The structures of eight 2,4,6-trisubstituted-5-nitrosopyrimidines (one of which crystallizes in two polymorphs) have been determined, including seven O
6-benzyl derivatives which are potential, or proven,
in vitro inhibitors of the human DNA-repair protein O
6-alkylguanine-DNA-transferase. In the derivatives having an amino substituent at the 4-position, an intramolecular N—H
O hydrogen bond with the nitroso O as an acceptor leads to an overall molecular shape similar to that of substituted purines. There is a marked propensity for these nitroso compounds to crystallize with
Z′ = 2. The structure of an analogue with no nitroso group is also reported for comparative purposes. Compounds containing the
N-alkyl substituents —NHCH
2COOEt, —NHCH
2CH
2COOEt and —NHCH(CH
2Ph)COOEt, derived from amino acid esters, exhibit a rich variety of conformational behaviour, and in all of the nitroso compounds the bond lengths provide strong evidence for a highly polarized electronic structure. Associated with this polarization is extensive charge-assisted hydrogen bonding between the molecules, leading to supramolecular aggregation in the form of finite (zero-dimensional) aggregates, chains, molecular ladders, sheets and frameworks.
Supporting information
| Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768101021607/na0133sup1.cif Contains datablocks global, 3, 4, 5A, 5B, 6, 7, 8, 9, 10, 11 |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101021607/na01333sup2.hkl Contains datablock 3 |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101021607/na01334sup3.hkl Contains datablock 4 |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101021607/na01335Asup4.hkl Contains datablock III |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101021607/na01335Bsup5.hkl Contains datablock IV |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101021607/na01336sup6.hkl Contains datablock 6 |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101021607/na01337sup7.hkl Contains datablock 7 |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101021607/na01338sup8.hkl Contains datablock 8 |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101021607/na01339sup9.hkl Contains datablock 9 |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101021607/na013310sup10.hkl Contains datablock IX |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101021607/na013311sup11.hkl Contains datablock X |
CCDC references: 184908; 184909; 184910; 184911; 184912; 184913; 184914; 184915; 184916; 184917
For all compounds, data collection: Kappa-CCD server software (Nonius, 1997). Cell refinement: DENZO-SMN (Otwinowski & Minor, 1997) for (3), (5A), (5B), (7), (8), (9), (10), (11); DENZO (Otwinowski & Minor, 1997) for (4), (6). Data reduction: DENZO-SMN (Otwinowski & Minor, 1997) for (3), (5A), (5B), (7), (8), (9), (10), (11); DENZO (Otwinowski & Minor, 1997) for (4), (6). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: PLATON (Spek, 2001). Software used to prepare material for publication: SHELXL97 (Sheldrick, 1997b) and PRPKAPPA (Ferguson, 1999) for (3), (4), (5A), (5B), (7), (8), (9), (10), (11); SHELXL97 SHELXL97 (Sheldrick, 1997b) and PRPKAPPA (Ferguson, 1999) for (6).
(3) 2-Amino-4-benzylamino-6-benzyloxy-5-nitrosopyrimidine
top
Crystal data top
C18H17N5O2 | F(000) = 1408 |
Mr = 335.37 | Dx = 1.362 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.677 (2) Å | Cell parameters from 21450 reflections |
b = 13.362 (3) Å | θ = 1.0–27.5° |
c = 21.478 (4) Å | µ = 0.09 mm−1 |
β = 102.58 (3)° | T = 150 K |
V = 3270.7 (11) Å3 | Block, purple |
Z = 8 | 0.34 × 0.18 × 0.18 mm |
Data collection top
Kappa-CCD diffractometer | 7334 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 4449 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.063 |
φ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 1.8° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −14→14 |
Tmin = 0.969, Tmax = 0.983 | k = −17→17 |
36834 measured reflections | l = −27→27 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0833P)2] where P = (Fo2 + 2Fc2)/3 |
7334 reflections | (Δ/σ)max = 0.001 |
451 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.41 e Å−3 |
Special details top
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm
[Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which
effectively corrects for absorption effects. High redundancy data were used in
the scaling program hence the 'multi-scan' code word was used. No transmission
coefficients are available from the program (only scale factors for each
frame). The scale factors in the experimental table are calculated from the
'size' command in the SHELXL97 input file. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N11 | 0.72275 (12) | 0.80433 (11) | 0.25679 (7) | 0.0225 (4) | |
C12 | 0.64409 (15) | 0.76915 (14) | 0.29038 (9) | 0.0215 (4) | |
N12 | 0.62340 (13) | 0.67198 (11) | 0.28445 (8) | 0.0268 (4) | |
N13 | 0.58763 (12) | 0.82167 (11) | 0.32740 (7) | 0.0225 (4) | |
C14 | 0.61234 (15) | 0.91950 (14) | 0.33366 (9) | 0.0209 (4) | |
C141 | 0.49667 (15) | 0.88079 (14) | 0.45839 (9) | 0.0241 (4) | |
C142 | 0.40942 (17) | 0.84741 (15) | 0.48737 (10) | 0.0300 (5) | |
C143 | 0.43522 (19) | 0.79373 (15) | 0.54365 (11) | 0.0358 (5) | |
C144 | 0.5494 (2) | 0.77246 (17) | 0.57219 (11) | 0.0401 (6) | |
C145 | 0.63678 (19) | 0.80565 (17) | 0.54421 (10) | 0.0393 (6) | |
C146 | 0.61181 (17) | 0.85974 (16) | 0.48770 (10) | 0.0322 (5) | |
C147 | 0.46236 (16) | 0.93826 (15) | 0.39689 (10) | 0.0275 (5) | |
N14 | 0.55851 (13) | 0.97465 (12) | 0.36995 (8) | 0.0250 (4) | |
C15 | 0.69525 (15) | 0.96644 (13) | 0.30181 (9) | 0.0211 (4) | |
N15 | 0.72645 (13) | 1.06334 (11) | 0.30250 (8) | 0.0261 (4) | |
O15 | 0.68109 (12) | 1.12291 (10) | 0.33691 (7) | 0.0315 (3) | |
C16 | 0.74592 (15) | 0.89990 (13) | 0.26271 (9) | 0.0205 (4) | |
C161 | 0.91781 (16) | 0.94421 (14) | 0.14578 (10) | 0.0244 (4) | |
C162 | 0.85096 (17) | 0.98018 (16) | 0.08877 (11) | 0.0351 (5) | |
C163 | 0.89713 (19) | 1.04988 (18) | 0.05312 (11) | 0.0446 (6) | |
C164 | 1.00978 (19) | 1.08450 (17) | 0.07418 (12) | 0.0414 (6) | |
C165 | 1.07737 (18) | 1.04791 (16) | 0.13024 (11) | 0.0351 (5) | |
C166 | 1.03279 (16) | 0.97820 (14) | 0.16600 (10) | 0.0273 (5) | |
C167 | 0.86425 (17) | 0.87567 (14) | 0.18617 (10) | 0.0294 (5) | |
O16 | 0.82046 (11) | 0.94060 (9) | 0.23052 (6) | 0.0256 (3) | |
N21 | 1.28017 (13) | 0.83599 (11) | 0.25079 (8) | 0.0234 (4) | |
C22 | 1.35551 (15) | 0.87739 (14) | 0.21750 (9) | 0.0217 (4) | |
N22 | 1.36975 (13) | 0.97493 (11) | 0.22494 (8) | 0.0282 (4) | |
N23 | 1.41586 (12) | 0.83015 (11) | 0.17965 (8) | 0.0229 (4) | |
C24 | 1.39762 (15) | 0.73157 (14) | 0.17216 (9) | 0.0211 (4) | |
C241 | 1.52442 (16) | 0.68368 (14) | 0.03603 (9) | 0.0249 (4) | |
C242 | 1.60612 (16) | 0.61795 (14) | 0.02028 (10) | 0.0274 (5) | |
C243 | 1.58884 (17) | 0.57701 (15) | −0.04033 (10) | 0.0311 (5) | |
C244 | 1.49054 (18) | 0.60106 (16) | −0.08612 (10) | 0.0343 (5) | |
C246 | 1.42553 (17) | 0.70853 (15) | −0.01085 (10) | 0.0311 (5) | |
C245 | 1.40869 (18) | 0.66696 (16) | −0.07109 (10) | 0.0361 (5) | |
C247 | 1.53934 (17) | 0.72553 (15) | 0.10228 (10) | 0.0287 (5) | |
N24 | 1.45421 (13) | 0.68138 (12) | 0.13498 (8) | 0.0246 (4) | |
C25 | 1.31737 (15) | 0.67867 (13) | 0.20373 (9) | 0.0219 (4) | |
N25 | 1.28927 (14) | 0.58079 (11) | 0.19968 (8) | 0.0286 (4) | |
O25 | 1.33788 (13) | 0.52564 (10) | 0.16443 (7) | 0.0377 (4) | |
C26 | 1.26368 (15) | 0.74022 (14) | 0.24356 (9) | 0.0219 (4) | |
C261 | 1.08612 (16) | 0.68076 (14) | 0.35586 (10) | 0.0260 (4) | |
C262 | 1.14663 (17) | 0.63364 (16) | 0.41034 (10) | 0.0333 (5) | |
C263 | 1.09523 (18) | 0.55771 (17) | 0.43825 (10) | 0.0380 (5) | |
C264 | 0.98147 (18) | 0.53005 (16) | 0.41231 (11) | 0.0348 (5) | |
C265 | 0.91835 (17) | 0.57870 (15) | 0.35897 (10) | 0.0286 (5) | |
C266 | 0.97098 (16) | 0.65294 (14) | 0.33053 (10) | 0.0258 (4) | |
C267 | 1.14750 (17) | 0.75406 (15) | 0.32164 (10) | 0.0319 (5) | |
O26 | 1.19289 (11) | 0.69385 (9) | 0.27542 (6) | 0.0273 (3) | |
H12A | 0.5773 | 0.6417 | 0.3061 | 0.032* | |
H12B | 0.6578 | 0.6331 | 0.2626 | 0.032* | |
H142 | 0.3298 | 0.8616 | 0.4682 | 0.036* | |
H143 | 0.3735 | 0.7715 | 0.5627 | 0.043* | |
H144 | 0.5674 | 0.7353 | 0.6108 | 0.048* | |
H145 | 0.7162 | 0.7914 | 0.5638 | 0.047* | |
H146 | 0.6739 | 0.8823 | 0.4691 | 0.039* | |
H14A | 0.4120 | 0.8947 | 0.3649 | 0.033* | |
H14B | 0.4143 | 0.9964 | 0.4041 | 0.033* | |
H14 | 0.5823 | 1.0367 | 0.3782 | 0.030* | |
H162 | 0.7729 | 0.9569 | 0.0740 | 0.042* | |
H163 | 0.8507 | 1.0738 | 0.0140 | 0.053* | |
H164 | 1.0408 | 1.1333 | 0.0502 | 0.050* | |
H165 | 1.1557 | 1.0710 | 0.1444 | 0.042* | |
H166 | 1.0805 | 0.9533 | 0.2045 | 0.033* | |
H16A | 0.7993 | 0.8369 | 0.1596 | 0.035* | |
H16B | 0.9235 | 0.8284 | 0.2096 | 0.035* | |
H22A | 1.4163 | 1.0032 | 0.2035 | 0.034* | |
H22B | 1.3210 | 1.0108 | 0.2469 | 0.034* | |
H242 | 1.6745 | 0.6010 | 0.0514 | 0.033* | |
H243 | 1.6452 | 0.5320 | −0.0504 | 0.037* | |
H244 | 1.4788 | 0.5728 | −0.1276 | 0.041* | |
H246 | 1.3695 | 0.7543 | −0.0013 | 0.037* | |
H245 | 1.3406 | 0.6836 | −0.1025 | 0.043* | |
H24A | 1.6198 | 0.7114 | 0.1268 | 0.034* | |
H24B | 1.5287 | 0.7990 | 0.0999 | 0.034* | |
H24 | 1.4395 | 0.6170 | 0.1296 | 0.029* | |
H262 | 1.2247 | 0.6537 | 0.4289 | 0.040* | |
H263 | 1.1383 | 0.5248 | 0.4752 | 0.046* | |
H264 | 0.9461 | 0.4773 | 0.4311 | 0.042* | |
H265 | 0.8389 | 0.5610 | 0.3420 | 0.034* | |
H266 | 0.9281 | 0.6853 | 0.2933 | 0.031* | |
H26A | 1.0921 | 0.8055 | 0.2997 | 0.038* | |
H26B | 1.2123 | 0.7877 | 0.3518 | 0.038* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N11 | 0.0246 (8) | 0.0199 (9) | 0.0236 (9) | 0.0011 (6) | 0.0062 (7) | 0.0010 (7) |
C12 | 0.0204 (10) | 0.0223 (10) | 0.0205 (11) | −0.0002 (7) | 0.0020 (8) | 0.0037 (8) |
N12 | 0.0293 (9) | 0.0199 (9) | 0.0337 (11) | −0.0020 (7) | 0.0124 (7) | 0.0002 (8) |
N13 | 0.0237 (8) | 0.0224 (9) | 0.0219 (9) | −0.0011 (6) | 0.0057 (7) | 0.0014 (7) |
C14 | 0.0212 (10) | 0.0235 (10) | 0.0177 (10) | 0.0001 (7) | 0.0034 (7) | 0.0011 (8) |
C141 | 0.0267 (10) | 0.0228 (10) | 0.0251 (11) | −0.0009 (8) | 0.0108 (8) | −0.0058 (9) |
C142 | 0.0282 (11) | 0.0298 (11) | 0.0349 (13) | −0.0011 (8) | 0.0135 (9) | −0.0046 (10) |
C143 | 0.0455 (14) | 0.0323 (12) | 0.0359 (14) | −0.0062 (9) | 0.0226 (11) | −0.0009 (10) |
C144 | 0.0516 (15) | 0.0419 (14) | 0.0286 (13) | 0.0004 (10) | 0.0131 (11) | 0.0057 (11) |
C145 | 0.0361 (12) | 0.0540 (15) | 0.0264 (13) | 0.0030 (10) | 0.0042 (9) | 0.0031 (11) |
C146 | 0.0310 (12) | 0.0426 (13) | 0.0250 (12) | −0.0027 (9) | 0.0101 (9) | −0.0013 (10) |
C147 | 0.0243 (11) | 0.0327 (12) | 0.0281 (12) | 0.0018 (8) | 0.0112 (8) | −0.0010 (9) |
N14 | 0.0312 (9) | 0.0223 (9) | 0.0237 (9) | −0.0022 (6) | 0.0113 (7) | −0.0026 (7) |
C15 | 0.0231 (10) | 0.0210 (10) | 0.0195 (10) | −0.0014 (7) | 0.0052 (8) | 0.0011 (8) |
N15 | 0.0317 (9) | 0.0232 (9) | 0.0238 (10) | −0.0014 (7) | 0.0074 (7) | −0.0027 (7) |
O15 | 0.0429 (9) | 0.0233 (8) | 0.0324 (9) | −0.0013 (6) | 0.0171 (7) | −0.0061 (6) |
C16 | 0.0197 (9) | 0.0225 (10) | 0.0194 (10) | −0.0002 (7) | 0.0047 (7) | 0.0033 (8) |
C161 | 0.0269 (10) | 0.0210 (10) | 0.0286 (12) | 0.0011 (7) | 0.0132 (8) | −0.0023 (9) |
C162 | 0.0225 (11) | 0.0478 (14) | 0.0356 (13) | −0.0031 (9) | 0.0078 (9) | 0.0018 (11) |
C163 | 0.0445 (14) | 0.0569 (16) | 0.0319 (14) | 0.0022 (11) | 0.0073 (10) | 0.0148 (12) |
C164 | 0.0471 (14) | 0.0398 (14) | 0.0425 (15) | −0.0035 (10) | 0.0212 (11) | 0.0103 (11) |
C165 | 0.0302 (12) | 0.0372 (13) | 0.0413 (14) | −0.0074 (9) | 0.0148 (10) | −0.0006 (11) |
C166 | 0.0254 (10) | 0.0298 (11) | 0.0270 (12) | 0.0013 (8) | 0.0063 (8) | 0.0002 (9) |
C167 | 0.0340 (11) | 0.0222 (11) | 0.0379 (13) | −0.0001 (8) | 0.0208 (9) | −0.0055 (9) |
O16 | 0.0318 (8) | 0.0224 (7) | 0.0271 (8) | −0.0034 (5) | 0.0162 (6) | −0.0018 (6) |
N21 | 0.0263 (9) | 0.0195 (9) | 0.0256 (10) | −0.0002 (6) | 0.0081 (7) | −0.0001 (7) |
C22 | 0.0219 (10) | 0.0214 (10) | 0.0206 (11) | 0.0005 (7) | 0.0023 (7) | 0.0002 (8) |
N22 | 0.0353 (9) | 0.0189 (9) | 0.0349 (11) | −0.0014 (7) | 0.0175 (8) | 0.0019 (7) |
N23 | 0.0258 (8) | 0.0205 (9) | 0.0229 (9) | −0.0002 (6) | 0.0067 (7) | −0.0002 (7) |
C24 | 0.0213 (10) | 0.0240 (11) | 0.0174 (10) | 0.0016 (7) | 0.0032 (7) | 0.0006 (8) |
C241 | 0.0261 (10) | 0.0251 (11) | 0.0258 (11) | −0.0072 (8) | 0.0104 (8) | 0.0013 (9) |
C242 | 0.0238 (10) | 0.0312 (11) | 0.0287 (12) | −0.0029 (8) | 0.0090 (8) | 0.0010 (9) |
C243 | 0.0320 (11) | 0.0329 (12) | 0.0328 (13) | −0.0046 (9) | 0.0169 (9) | −0.0044 (10) |
C244 | 0.0420 (13) | 0.0394 (13) | 0.0244 (12) | −0.0139 (10) | 0.0137 (9) | −0.0036 (10) |
C246 | 0.0277 (11) | 0.0347 (12) | 0.0330 (13) | 0.0014 (8) | 0.0110 (9) | 0.0039 (10) |
C245 | 0.0345 (12) | 0.0450 (14) | 0.0268 (12) | −0.0080 (10) | 0.0025 (9) | 0.0097 (11) |
C247 | 0.0275 (11) | 0.0318 (12) | 0.0302 (12) | −0.0058 (8) | 0.0137 (9) | −0.0038 (9) |
N24 | 0.0280 (9) | 0.0219 (9) | 0.0267 (10) | −0.0025 (6) | 0.0124 (7) | −0.0029 (7) |
C25 | 0.0271 (10) | 0.0190 (10) | 0.0204 (11) | −0.0004 (7) | 0.0071 (8) | −0.0012 (8) |
N25 | 0.0381 (10) | 0.0217 (9) | 0.0291 (10) | 0.0008 (7) | 0.0143 (8) | −0.0036 (8) |
O25 | 0.0547 (10) | 0.0252 (8) | 0.0411 (10) | −0.0014 (6) | 0.0275 (8) | −0.0074 (7) |
C26 | 0.0215 (10) | 0.0214 (11) | 0.0226 (11) | −0.0016 (7) | 0.0045 (8) | 0.0015 (8) |
C261 | 0.0289 (11) | 0.0259 (11) | 0.0275 (12) | −0.0015 (8) | 0.0152 (8) | −0.0071 (9) |
C262 | 0.0238 (11) | 0.0498 (14) | 0.0274 (12) | −0.0024 (9) | 0.0081 (9) | −0.0079 (10) |
C263 | 0.0336 (12) | 0.0560 (15) | 0.0252 (12) | 0.0073 (10) | 0.0084 (9) | 0.0081 (11) |
C264 | 0.0401 (12) | 0.0358 (13) | 0.0333 (13) | −0.0006 (9) | 0.0186 (10) | 0.0040 (10) |
C265 | 0.0252 (10) | 0.0299 (11) | 0.0314 (12) | −0.0018 (8) | 0.0075 (8) | −0.0043 (9) |
C266 | 0.0281 (10) | 0.0263 (11) | 0.0248 (11) | 0.0033 (8) | 0.0092 (8) | −0.0004 (9) |
C267 | 0.0364 (12) | 0.0277 (12) | 0.0388 (14) | −0.0039 (9) | 0.0240 (10) | −0.0101 (10) |
O26 | 0.0345 (8) | 0.0213 (7) | 0.0314 (8) | −0.0041 (5) | 0.0189 (6) | −0.0049 (6) |
Geometric parameters (Å, º) top
N11—C16 | 1.306 (2) | N21—C26 | 1.298 (2) |
N11—C12 | 1.369 (2) | N21—C22 | 1.366 (2) |
C12—N12 | 1.322 (2) | C22—N22 | 1.319 (2) |
C12—N13 | 1.337 (2) | C22—N23 | 1.344 (2) |
N12—H12A | 0.88 | N22—H22A | 0.87 |
N12—H12B | 0.86 | N22—H22B | 0.94 |
N13—C14 | 1.339 (2) | N23—C24 | 1.338 (2) |
C14—N14 | 1.326 (2) | C24—N24 | 1.324 (2) |
C14—C15 | 1.445 (2) | C24—C25 | 1.454 (2) |
C141—C142 | 1.379 (3) | C241—C242 | 1.392 (3) |
C141—C146 | 1.384 (3) | C241—C246 | 1.397 (3) |
C141—C147 | 1.505 (3) | C241—C247 | 1.503 (3) |
C142—C143 | 1.381 (3) | C242—C243 | 1.386 (3) |
C142—H142 | 0.9500 | C242—H242 | 0.9500 |
C143—C144 | 1.370 (3) | C243—C244 | 1.377 (3) |
C143—H143 | 0.9500 | C243—H243 | 0.9500 |
C144—C145 | 1.366 (3) | C244—C245 | 1.388 (3) |
C144—H144 | 0.9500 | C244—H244 | 0.9500 |
C145—C146 | 1.388 (3) | C246—C245 | 1.382 (3) |
C145—H145 | 0.9500 | C246—H246 | 0.9500 |
C146—H146 | 0.9500 | C245—H245 | 0.9500 |
C147—N14 | 1.454 (2) | C247—N24 | 1.461 (2) |
C147—H14A | 0.9900 | C247—H24A | 0.9900 |
C147—H14B | 0.9900 | C247—H24B | 0.9900 |
N14—H14 | 0.88 | N24—H24 | 0.88 |
C15—N15 | 1.344 (2) | C25—N25 | 1.347 (2) |
C15—C16 | 1.436 (3) | C25—C26 | 1.426 (2) |
N15—O15 | 1.2772 (19) | N25—O25 | 1.275 (2) |
C16—O16 | 1.339 (2) | C26—O26 | 1.335 (2) |
C161—C162 | 1.387 (3) | C261—C262 | 1.380 (3) |
C161—C166 | 1.394 (3) | C261—C266 | 1.387 (3) |
C161—C167 | 1.490 (3) | C261—C267 | 1.498 (3) |
C162—C163 | 1.387 (3) | C262—C263 | 1.380 (3) |
C162—H162 | 0.9500 | C262—H262 | 0.9500 |
C163—C164 | 1.375 (3) | C263—C264 | 1.375 (3) |
C163—H163 | 0.9500 | C263—H263 | 0.9500 |
C164—C165 | 1.378 (3) | C264—C265 | 1.382 (3) |
C164—H164 | 0.9500 | C264—H264 | 0.9500 |
C165—C166 | 1.379 (3) | C265—C266 | 1.378 (3) |
C165—H165 | 0.9500 | C265—H265 | 0.9500 |
C166—H166 | 0.9500 | C266—H266 | 0.9500 |
C167—O16 | 1.461 (2) | C267—O26 | 1.464 (2) |
C167—H16A | 0.9900 | C267—H26A | 0.9900 |
C167—H16B | 0.9900 | C267—H26B | 0.9900 |
| | | |
C16—N11—C12 | 115.66 (15) | C26—N21—C22 | 115.61 (16) |
N12—C12—N13 | 118.00 (16) | N22—C22—N23 | 117.94 (16) |
N12—C12—N11 | 114.59 (16) | N22—C22—N21 | 114.54 (16) |
N13—C12—N11 | 127.41 (17) | N23—C22—N21 | 127.51 (17) |
C12—N12—H12A | 121.3 | C22—N22—H22A | 116.2 |
C12—N12—H12B | 123.5 | C22—N22—H22B | 119.2 |
H12A—N12—H12B | 115.0 | H22A—N22—H22B | 123.8 |
C12—N13—C14 | 116.67 (15) | C24—N23—C22 | 116.39 (15) |
N14—C14—N13 | 118.82 (16) | N24—C24—N23 | 118.92 (16) |
N14—C14—C15 | 119.29 (17) | N24—C24—C25 | 119.46 (16) |
N13—C14—C15 | 121.88 (16) | N23—C24—C25 | 121.61 (16) |
C142—C141—C146 | 117.99 (19) | C242—C241—C246 | 118.54 (19) |
C142—C141—C147 | 118.67 (17) | C242—C241—C247 | 121.38 (18) |
C146—C141—C147 | 123.35 (17) | C246—C241—C247 | 120.07 (18) |
C141—C142—C143 | 121.42 (19) | C243—C242—C241 | 120.68 (19) |
C141—C142—H142 | 119.3 | C243—C242—H242 | 119.7 |
C143—C142—H142 | 119.3 | C241—C242—H242 | 119.7 |
C144—C143—C142 | 120.32 (19) | C244—C243—C242 | 120.46 (19) |
C144—C143—H143 | 119.8 | C244—C243—H243 | 119.8 |
C142—C143—H143 | 119.8 | C242—C243—H243 | 119.8 |
C145—C144—C143 | 118.9 (2) | C243—C244—C245 | 119.4 (2) |
C145—C144—H144 | 120.6 | C243—C244—H244 | 120.3 |
C143—C144—H144 | 120.6 | C245—C244—H244 | 120.3 |
C144—C145—C146 | 121.3 (2) | C245—C246—C241 | 120.40 (19) |
C144—C145—H145 | 119.4 | C245—C246—H246 | 119.8 |
C146—C145—H145 | 119.4 | C241—C246—H246 | 119.8 |
C141—C146—C145 | 120.13 (19) | C246—C245—C244 | 120.5 (2) |
C141—C146—H146 | 119.9 | C246—C245—H245 | 119.7 |
C145—C146—H146 | 119.9 | C244—C245—H245 | 119.7 |
N14—C147—C141 | 116.03 (15) | N24—C247—C241 | 110.75 (15) |
N14—C147—H14A | 108.3 | N24—C247—H24A | 109.5 |
C141—C147—H14A | 108.3 | C241—C247—H24A | 109.5 |
N14—C147—H14B | 108.3 | N24—C247—H24B | 109.5 |
C141—C147—H14B | 108.3 | C241—C247—H24B | 109.5 |
H14A—C147—H14B | 107.4 | H24A—C247—H24B | 108.1 |
C14—N14—C147 | 123.62 (16) | C24—N24—C247 | 124.51 (16) |
C14—N14—H14 | 118.2 | C24—N24—H24 | 117.7 |
C147—N14—H14 | 118.2 | C247—N24—H24 | 117.7 |
N15—C15—C16 | 117.23 (16) | N25—C25—C26 | 117.78 (16) |
N15—C15—C14 | 128.39 (17) | N25—C25—C24 | 127.93 (16) |
C16—C15—C14 | 114.33 (16) | C26—C25—C24 | 114.30 (16) |
O15—N15—C15 | 117.46 (15) | O25—N25—C25 | 117.78 (15) |
N11—C16—O16 | 119.41 (16) | N21—C26—O26 | 119.23 (16) |
N11—C16—C15 | 124.02 (16) | N21—C26—C25 | 124.54 (16) |
O16—C16—C15 | 116.57 (16) | O26—C26—C25 | 116.23 (16) |
C162—C161—C166 | 118.75 (18) | C262—C261—C266 | 118.94 (18) |
C162—C161—C167 | 120.02 (18) | C262—C261—C267 | 120.21 (18) |
C166—C161—C167 | 121.12 (19) | C266—C261—C267 | 120.63 (19) |
C161—C162—C163 | 120.55 (19) | C261—C262—C263 | 120.84 (19) |
C161—C162—H162 | 119.7 | C261—C262—H262 | 119.6 |
C163—C162—H162 | 119.7 | C263—C262—H262 | 119.6 |
C164—C163—C162 | 120.2 (2) | C264—C263—C262 | 119.7 (2) |
C164—C163—H163 | 119.9 | C264—C263—H263 | 120.2 |
C162—C163—H163 | 119.9 | C262—C263—H263 | 120.2 |
C163—C164—C165 | 119.5 (2) | C263—C264—C265 | 120.2 (2) |
C163—C164—H164 | 120.2 | C263—C264—H264 | 119.9 |
C165—C164—H164 | 120.2 | C265—C264—H264 | 119.9 |
C164—C165—C166 | 120.8 (2) | C266—C265—C264 | 119.82 (19) |
C164—C165—H165 | 119.6 | C266—C265—H265 | 120.1 |
C166—C165—H165 | 119.6 | C264—C265—H265 | 120.1 |
C165—C166—C161 | 120.1 (2) | C265—C266—C261 | 120.46 (19) |
C165—C166—H166 | 120.0 | C265—C266—H266 | 119.8 |
C161—C166—H166 | 120.0 | C261—C266—H266 | 119.8 |
O16—C167—C161 | 105.41 (14) | O26—C267—C261 | 104.84 (15) |
O16—C167—H16A | 110.7 | O26—C267—H26A | 110.8 |
C161—C167—H16A | 110.7 | C261—C267—H26A | 110.8 |
O16—C167—H16B | 110.7 | O26—C267—H26B | 110.8 |
C161—C167—H16B | 110.7 | C261—C267—H26B | 110.8 |
H16A—C167—H16B | 108.8 | H26A—C267—H26B | 108.9 |
C16—O16—C167 | 117.04 (14) | C26—O26—C267 | 116.66 (14) |
| | | |
C16—N11—C12—N12 | −179.00 (16) | C26—N21—C22—N22 | 179.18 (16) |
C16—N11—C12—N13 | 1.1 (3) | C26—N21—C22—N23 | −1.6 (3) |
N12—C12—N13—C14 | 178.53 (16) | N22—C22—N23—C24 | −178.73 (16) |
N11—C12—N13—C14 | −1.6 (3) | N21—C22—N23—C24 | 2.1 (3) |
C12—N13—C14—N14 | −179.96 (16) | C22—N23—C24—N24 | 179.52 (16) |
C12—N13—C14—C15 | 0.4 (2) | C22—N23—C24—C25 | −0.4 (3) |
C146—C141—C142—C143 | −0.6 (3) | C246—C241—C242—C243 | −0.9 (3) |
C147—C141—C142—C143 | 179.59 (19) | C247—C241—C242—C243 | 177.49 (17) |
C141—C142—C143—C144 | 0.1 (3) | C241—C242—C243—C244 | 0.2 (3) |
C142—C143—C144—C145 | 0.3 (3) | C242—C243—C244—C245 | 0.1 (3) |
C143—C144—C145—C146 | −0.3 (3) | C242—C241—C246—C245 | 1.2 (3) |
C142—C141—C146—C145 | 0.6 (3) | C247—C241—C246—C245 | −177.20 (18) |
C147—C141—C146—C145 | −179.5 (2) | C241—C246—C245—C244 | −0.9 (3) |
C144—C145—C146—C141 | −0.2 (3) | C243—C244—C245—C246 | 0.2 (3) |
C142—C141—C147—N14 | 177.77 (17) | C242—C241—C247—N24 | −108.39 (19) |
C146—C141—C147—N14 | −2.1 (3) | C246—C241—C247—N24 | 70.0 (2) |
N13—C14—N14—C147 | −8.4 (3) | N23—C24—N24—C247 | 1.9 (3) |
C15—C14—N14—C147 | 171.22 (17) | C25—C24—N24—C247 | −178.15 (17) |
C141—C147—N14—C14 | 83.8 (2) | C241—C247—N24—C24 | −139.77 (18) |
N14—C14—C15—N15 | −1.3 (3) | N24—C24—C25—N25 | −1.2 (3) |
N13—C14—C15—N15 | 178.33 (18) | N23—C24—C25—N25 | 178.77 (18) |
N14—C14—C15—C16 | −178.62 (16) | N24—C24—C25—C26 | 178.69 (16) |
N13—C14—C15—C16 | 1.0 (3) | N23—C24—C25—C26 | −1.4 (3) |
C16—C15—N15—O15 | 179.60 (16) | C26—C25—N25—O25 | −179.52 (17) |
C14—C15—N15—O15 | 2.4 (3) | C24—C25—N25—O25 | 0.3 (3) |
C12—N11—C16—O16 | −178.85 (15) | C22—N21—C26—O26 | 178.79 (16) |
C12—N11—C16—C15 | 0.6 (3) | C22—N21—C26—C25 | −0.6 (3) |
N15—C15—C16—N11 | −179.18 (17) | N25—C25—C26—N21 | −178.21 (18) |
C14—C15—C16—N11 | −1.6 (3) | C24—C25—C26—N21 | 1.9 (3) |
N15—C15—C16—O16 | 0.3 (2) | N25—C25—C26—O26 | 2.4 (2) |
C14—C15—C16—O16 | 177.88 (15) | C24—C25—C26—O26 | −177.45 (16) |
C166—C161—C162—C163 | −1.0 (3) | C266—C261—C262—C263 | 2.1 (3) |
C167—C161—C162—C163 | 175.11 (19) | C267—C261—C262—C263 | −172.52 (18) |
C161—C162—C163—C164 | −0.3 (3) | C261—C262—C263—C264 | −1.4 (3) |
C162—C163—C164—C165 | 1.4 (4) | C262—C263—C264—C265 | −0.7 (3) |
C163—C164—C165—C166 | −1.1 (3) | C263—C264—C265—C266 | 2.1 (3) |
C164—C165—C166—C161 | −0.3 (3) | C264—C265—C266—C261 | −1.4 (3) |
C162—C161—C166—C165 | 1.4 (3) | C262—C261—C266—C265 | −0.7 (3) |
C167—C161—C166—C165 | −174.74 (18) | C267—C261—C266—C265 | 173.92 (17) |
C162—C161—C167—O16 | −91.9 (2) | C262—C261—C267—O26 | 90.1 (2) |
C166—C161—C167—O16 | 84.2 (2) | C266—C261—C267—O26 | −84.4 (2) |
N11—C16—O16—C167 | 4.9 (2) | N21—C26—O26—C267 | −5.9 (3) |
C15—C16—O16—C167 | −174.58 (16) | C25—C26—O26—C267 | 173.54 (16) |
C161—C167—O16—C16 | 165.71 (15) | C261—C267—O26—C26 | −172.39 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N14—H14···O15 | 0.88 | 1.97 | 2.630 (2) | 131 |
N24—H24···O25 | 0.88 | 1.96 | 2.636 (2) | 133 |
N12—H12B···N15i | 0.86 | 2.34 | 3.177 (2) | 166 |
N22—H22B···N25ii | 0.94 | 2.12 | 3.063 (2) | 175 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+5/2, y+1/2, −z+1/2. |
(4) Ethyl
N-(2-amino-6-benzyloxypyrimidin-4-yl)gylcinate
top
Crystal data top
C15H17N5O4 | Z = 2 |
Mr = 331.34 | F(000) = 348 |
Triclinic, P1 | Dx = 1.411 Mg m−3 |
a = 7.3525 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.5420 (5) Å | Cell parameters from 11231 reflections |
c = 14.9454 (13) Å | θ = 1.0–27.5° |
α = 91.797 (3)° | µ = 0.11 mm−1 |
β = 100.467 (3)° | T = 150 K |
γ = 106.102 (6)° | Needle, violet |
V = 780.06 (10) Å3 | 0.50 × 0.20 × 0.10 mm |
Data collection top
Kappa-CCD diffractometer | 3418 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 1860 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.065 |
φ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 1.4° |
Absorption correction: multi-scan Sortav (Blessing, 1995 & 1997) | h = −9→9 |
Tmin = 0.949, Tmax = 0.990 | k = −9→9 |
10165 measured reflections | l = −19→19 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0778P)2] where P = (Fo2 + 2Fc2)/3 |
3418 reflections | (Δ/σ)max < 0.001 |
218 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.51 e Å−3 |
Special details top
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm
[Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which
effectively corrects for absorption effects. High redundancy data were used in
the scaling program hence the 'multi-scan' code word was used. No transmission
coefficients are available from the program (only scale factors for each
frame). The scale factors in the experimental table are calculated from the
'size' command in the SHELXL97 input file. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.4868 (3) | 0.8017 (3) | 0.42584 (13) | 0.0264 (5) | |
C2 | 0.6363 (3) | 0.7661 (3) | 0.48421 (16) | 0.0255 (5) | |
N2 | 0.7993 (3) | 0.7959 (3) | 0.45505 (14) | 0.0331 (5) | |
N3 | 0.6330 (3) | 0.7038 (3) | 0.56703 (13) | 0.0265 (5) | |
C4 | 0.4658 (3) | 0.6690 (3) | 0.59524 (16) | 0.0245 (5) | |
N4 | 0.4573 (3) | 0.6023 (3) | 0.67613 (13) | 0.0288 (5) | |
C5 | 0.2981 (3) | 0.7031 (3) | 0.54129 (16) | 0.0239 (5) | |
N5 | 0.1237 (3) | 0.6805 (3) | 0.56383 (13) | 0.0288 (5) | |
O5 | 0.0994 (2) | 0.6172 (2) | 0.64024 (11) | 0.0347 (5) | |
C6 | 0.3243 (3) | 0.7695 (3) | 0.45470 (16) | 0.0239 (5) | |
O6 | 0.1708 (2) | 0.7983 (2) | 0.40071 (10) | 0.0271 (4) | |
C67 | 0.1965 (3) | 0.8561 (3) | 0.31110 (16) | 0.0288 (6) | |
C61 | 0.0016 (3) | 0.8490 (3) | 0.25717 (16) | 0.0286 (6) | |
C62 | −0.0762 (4) | 0.9941 (4) | 0.26918 (18) | 0.0362 (6) | |
C63 | −0.2574 (4) | 0.9871 (4) | 0.2210 (2) | 0.0489 (8) | |
C64 | −0.3588 (4) | 0.8399 (5) | 0.1593 (2) | 0.0573 (9) | |
C65 | −0.2833 (4) | 0.6944 (5) | 0.1459 (2) | 0.0528 (8) | |
C66 | −0.1029 (4) | 0.6981 (4) | 0.19537 (18) | 0.0389 (7) | |
C7 | 0.6207 (3) | 0.5638 (3) | 0.73296 (16) | 0.0298 (6) | |
O81 | 0.6461 (3) | 0.8241 (3) | 0.83713 (13) | 0.0445 (5) | |
C8 | 0.7069 (3) | 0.7010 (4) | 0.81541 (16) | 0.0307 (6) | |
O82 | 0.8650 (2) | 0.6655 (2) | 0.86189 (11) | 0.0368 (5) | |
C9 | 0.9701 (4) | 0.7979 (4) | 0.93927 (18) | 0.0440 (7) | |
C10 | 1.1550 (4) | 0.7549 (5) | 0.9771 (2) | 0.0610 (9) | |
H2A | 0.9004 | 0.7751 | 0.4895 | 0.040* | |
H2B | 0.8074 | 0.8369 | 0.4010 | 0.040* | |
H4 | 0.3480 | 0.5807 | 0.6958 | 0.035* | |
H67A | 0.2531 | 0.7723 | 0.2804 | 0.035* | |
H67B | 0.2845 | 0.9836 | 0.3166 | 0.035* | |
H62 | −0.0045 | 1.0984 | 0.3107 | 0.043* | |
H63 | −0.3117 | 1.0849 | 0.2308 | 0.059* | |
H64 | −0.4821 | 0.8373 | 0.1252 | 0.069* | |
H65 | −0.3547 | 0.5923 | 0.1030 | 0.063* | |
H66 | −0.0512 | 0.5978 | 0.1870 | 0.047* | |
H7A | 0.7208 | 0.5663 | 0.6964 | 0.036* | |
H7B | 0.5792 | 0.4378 | 0.7533 | 0.036* | |
H9A | 0.8910 | 0.7900 | 0.9868 | 0.053* | |
H9B | 0.9984 | 0.9252 | 0.9197 | 0.053* | |
H10A | 1.1258 | 0.6307 | 0.9987 | 0.091* | |
H10B | 1.2292 | 0.8461 | 1.0282 | 0.091* | |
H10C | 1.2310 | 0.7598 | 0.9293 | 0.091* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0205 (10) | 0.0291 (12) | 0.0306 (12) | 0.0094 (8) | 0.0044 (8) | 0.0010 (9) |
C2 | 0.0212 (13) | 0.0249 (14) | 0.0305 (14) | 0.0079 (10) | 0.0041 (10) | −0.0018 (11) |
N2 | 0.0223 (11) | 0.0458 (14) | 0.0324 (13) | 0.0112 (9) | 0.0057 (9) | 0.0064 (10) |
N3 | 0.0200 (10) | 0.0296 (12) | 0.0302 (12) | 0.0092 (8) | 0.0027 (8) | 0.0011 (9) |
C4 | 0.0247 (13) | 0.0223 (13) | 0.0260 (14) | 0.0083 (10) | 0.0020 (10) | −0.0035 (10) |
N4 | 0.0258 (11) | 0.0352 (13) | 0.0265 (12) | 0.0112 (9) | 0.0035 (8) | 0.0049 (10) |
C5 | 0.0196 (12) | 0.0245 (13) | 0.0283 (14) | 0.0088 (9) | 0.0034 (9) | −0.0009 (10) |
N5 | 0.0272 (12) | 0.0318 (12) | 0.0278 (12) | 0.0090 (9) | 0.0062 (9) | 0.0019 (9) |
O5 | 0.0315 (10) | 0.0448 (11) | 0.0320 (11) | 0.0141 (8) | 0.0111 (7) | 0.0094 (9) |
C6 | 0.0209 (13) | 0.0225 (13) | 0.0285 (14) | 0.0093 (9) | 0.0010 (10) | −0.0021 (10) |
O6 | 0.0227 (9) | 0.0349 (10) | 0.0269 (10) | 0.0126 (7) | 0.0051 (7) | 0.0075 (7) |
C67 | 0.0271 (13) | 0.0352 (15) | 0.0261 (14) | 0.0122 (11) | 0.0055 (10) | 0.0052 (11) |
C61 | 0.0278 (13) | 0.0328 (15) | 0.0277 (14) | 0.0106 (11) | 0.0077 (10) | 0.0098 (12) |
C62 | 0.0354 (15) | 0.0406 (16) | 0.0375 (16) | 0.0152 (12) | 0.0112 (12) | 0.0110 (13) |
C63 | 0.0393 (17) | 0.061 (2) | 0.057 (2) | 0.0264 (15) | 0.0138 (15) | 0.0282 (17) |
C64 | 0.0314 (16) | 0.087 (3) | 0.052 (2) | 0.0167 (17) | 0.0020 (14) | 0.031 (2) |
C65 | 0.0394 (17) | 0.066 (2) | 0.0369 (18) | −0.0061 (15) | −0.0007 (13) | 0.0014 (15) |
C66 | 0.0366 (15) | 0.0425 (17) | 0.0333 (16) | 0.0047 (12) | 0.0061 (12) | 0.0037 (13) |
C7 | 0.0315 (14) | 0.0318 (15) | 0.0266 (14) | 0.0124 (11) | 0.0018 (10) | 0.0032 (11) |
O81 | 0.0480 (12) | 0.0451 (12) | 0.0425 (12) | 0.0233 (10) | 0.0005 (9) | −0.0075 (9) |
C8 | 0.0318 (14) | 0.0338 (16) | 0.0272 (14) | 0.0102 (11) | 0.0053 (11) | 0.0088 (12) |
O82 | 0.0376 (10) | 0.0370 (11) | 0.0317 (10) | 0.0123 (8) | −0.0055 (8) | 0.0002 (8) |
C9 | 0.0481 (17) | 0.0422 (18) | 0.0316 (16) | 0.0062 (13) | −0.0062 (13) | −0.0029 (13) |
C10 | 0.0484 (19) | 0.060 (2) | 0.060 (2) | 0.0103 (15) | −0.0169 (15) | 0.0090 (17) |
Geometric parameters (Å, º) top
N1—C6 | 1.306 (3) | C62—C63 | 1.381 (4) |
N1—C2 | 1.368 (3) | C62—H62 | 0.9500 |
C2—N2 | 1.312 (3) | C63—C64 | 1.366 (4) |
C2—N3 | 1.339 (3) | C63—H63 | 0.9500 |
N2—H2A | 0.88 | C64—C65 | 1.385 (5) |
N2—H2B | 0.88 | C64—H64 | 0.9500 |
N3—C4 | 1.332 (3) | C65—C66 | 1.388 (4) |
C4—N4 | 1.329 (3) | C65—H65 | 0.9500 |
C4—C5 | 1.436 (3) | C66—H66 | 0.9500 |
N4—C7 | 1.445 (3) | C7—C8 | 1.504 (3) |
N4—H4 | 0.88 | C7—H7A | 0.9900 |
C5—N5 | 1.352 (3) | C7—H7B | 0.9900 |
C5—C6 | 1.428 (3) | O81—C8 | 1.196 (3) |
N5—O5 | 1.275 (2) | C8—O82 | 1.341 (3) |
C6—O6 | 1.337 (3) | O82—C9 | 1.451 (3) |
O6—C67 | 1.450 (3) | C9—C10 | 1.500 (4) |
C67—C61 | 1.498 (3) | C9—H9A | 0.9900 |
C67—H67A | 0.9900 | C9—H9B | 0.9900 |
C67—H67B | 0.9900 | C10—H10A | 0.9800 |
C61—C62 | 1.388 (3) | C10—H10B | 0.9800 |
C61—C66 | 1.389 (4) | C10—H10C | 0.9800 |
| | | |
C6—N1—C2 | 115.6 (2) | C64—C63—C62 | 120.1 (3) |
N2—C2—N3 | 117.2 (2) | C64—C63—H63 | 119.9 |
N2—C2—N1 | 115.9 (2) | C62—C63—H63 | 119.9 |
N3—C2—N1 | 126.9 (2) | C63—C64—C65 | 120.5 (3) |
C2—N2—H2A | 120.0 | C63—C64—H64 | 119.8 |
C2—N2—H2B | 120.0 | C65—C64—H64 | 119.8 |
H2A—N2—H2B | 120.0 | C64—C65—C66 | 119.9 (3) |
C4—N3—C2 | 116.93 (19) | C64—C65—H65 | 120.1 |
N4—C4—N3 | 118.1 (2) | C66—C65—H65 | 120.1 |
N4—C4—C5 | 120.0 (2) | C65—C66—C61 | 119.7 (3) |
N3—C4—C5 | 121.9 (2) | C65—C66—H66 | 120.2 |
C4—N4—C7 | 122.43 (19) | C61—C66—H66 | 120.2 |
C4—N4—H4 | 118.8 | N4—C7—C8 | 112.5 (2) |
C7—N4—H4 | 118.8 | N4—C7—H7A | 109.1 |
N5—C5—C6 | 118.0 (2) | C8—C7—H7A | 109.1 |
N5—C5—C4 | 127.4 (2) | N4—C7—H7B | 109.1 |
C6—C5—C4 | 114.59 (19) | C8—C7—H7B | 109.1 |
O5—N5—C5 | 117.87 (19) | H7A—C7—H7B | 107.8 |
N1—C6—O6 | 119.0 (2) | O81—C8—O82 | 124.4 (2) |
N1—C6—C5 | 124.0 (2) | O81—C8—C7 | 126.0 (2) |
O6—C6—C5 | 116.94 (19) | O82—C8—C7 | 109.6 (2) |
C6—O6—C67 | 116.35 (17) | C8—O82—C9 | 114.8 (2) |
O6—C67—C61 | 107.39 (18) | O82—C9—C10 | 108.8 (2) |
O6—C67—H67A | 110.2 | O82—C9—H9A | 109.9 |
C61—C67—H67A | 110.2 | C10—C9—H9A | 109.9 |
O6—C67—H67B | 110.2 | O82—C9—H9B | 109.9 |
C61—C67—H67B | 110.2 | C10—C9—H9B | 109.9 |
H67A—C67—H67B | 108.5 | H9A—C9—H9B | 108.3 |
C62—C61—C66 | 119.6 (2) | C9—C10—H10A | 109.5 |
C62—C61—C67 | 119.8 (2) | C9—C10—H10B | 109.5 |
C66—C61—C67 | 120.6 (2) | H10A—C10—H10B | 109.5 |
C63—C62—C61 | 120.2 (3) | C9—C10—H10C | 109.5 |
C63—C62—H62 | 119.9 | H10A—C10—H10C | 109.5 |
C61—C62—H62 | 119.9 | H10B—C10—H10C | 109.5 |
| | | |
C6—N1—C2—N2 | 179.2 (2) | N1—C6—O6—C67 | 2.7 (3) |
C6—N1—C2—N3 | −0.6 (3) | C5—C6—O6—C67 | −176.80 (19) |
N2—C2—N3—C4 | −178.3 (2) | C6—O6—C67—C61 | 170.59 (19) |
N1—C2—N3—C4 | 1.5 (4) | O6—C67—C61—C62 | 81.0 (3) |
C2—N3—C4—N4 | 178.2 (2) | O6—C67—C61—C66 | −98.7 (3) |
C2—N3—C4—C5 | −2.3 (3) | C66—C61—C62—C63 | 1.0 (4) |
N3—C4—N4—C7 | −1.1 (3) | C67—C61—C62—C63 | −178.8 (2) |
C5—C4—N4—C7 | 179.5 (2) | C61—C62—C63—C64 | −1.9 (4) |
N4—C4—C5—N5 | 2.3 (4) | C62—C63—C64—C65 | 1.5 (4) |
N3—C4—C5—N5 | −177.2 (2) | C63—C64—C65—C66 | −0.2 (4) |
N4—C4—C5—C6 | −178.2 (2) | C64—C65—C66—C61 | −0.8 (4) |
N3—C4—C5—C6 | 2.3 (3) | C62—C61—C66—C65 | 0.4 (4) |
C6—C5—N5—O5 | 178.4 (2) | C67—C61—C66—C65 | −179.9 (2) |
C4—C5—N5—O5 | −2.1 (3) | C4—N4—C7—C8 | 108.0 (2) |
C2—N1—C6—O6 | −178.95 (19) | N4—C7—C8—O81 | 3.9 (4) |
C2—N1—C6—C5 | 0.5 (3) | N4—C7—C8—O82 | −175.88 (19) |
N5—C5—C6—N1 | 178.2 (2) | O81—C8—O82—C9 | −4.4 (4) |
C4—C5—C6—N1 | −1.4 (3) | C7—C8—O82—C9 | 175.4 (2) |
N5—C5—C6—O6 | −2.3 (3) | C8—O82—C9—C10 | −172.9 (2) |
C4—C5—C6—O6 | 178.12 (19) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O5 | 0.88 | 1.96 | 2.623 (2) | 131 |
N2—H2A···N5i | 0.88 | 2.12 | 2.987 (2) | 171 |
Symmetry code: (i) x+1, y, z. |
(5A) Ethyl
N-(2-amino-6 benzyloxy-5-nitrosopyrimidin-4-yl)-
β-alaninate
top
Crystal data top
C16H19N5O4 | F(000) = 728 |
Mr = 345.36 | Dx = 1.458 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 5.2399 (16) Å | Cell parameters from 66201 reflections |
b = 31.1630 (14) Å | θ = 1.0–27.5° |
c = 9.792 (4) Å | µ = 0.11 mm−1 |
β = 100.200 (12)° | T = 150 K |
V = 1573.7 (8) Å3 | Plate, blue |
Z = 4 | 0.20 × 0.10 × 0.02 mm |
Data collection top
Kappa-CCD diffractometer | 2525 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 822 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.065 |
φ scans, and ω scans with κ offsets | θmax = 25.0°, θmin = 2.5° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −6→6 |
Tmin = 0.979, Tmax = 0.998 | k = −36→37 |
10470 measured reflections | l = −11→11 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.106 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.283 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0757P)2 + 2.3684P] where P = (Fo2 + 2Fc2)/3 |
2525 reflections | (Δ/σ)max = 0.002 |
227 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Special details top
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm
[Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which
effectively corrects for absorption effects. High redundancy data were used in
the scaling program hence the 'multi-scan' code word was used. No transmission
coefficients are available from the program (only scale factors for each
frame). The scale factors in the experimental table are calculated from the
'size' command in the SHELXL97 input file. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.9265 (14) | 0.4168 (2) | 0.2453 (7) | 0.053 (2) | |
C2 | 0.9267 (19) | 0.4508 (3) | 0.3336 (8) | 0.058 (3) | |
N2 | 1.1277 (13) | 0.4505 (2) | 0.4369 (7) | 0.059 (2) | |
N3 | 0.7538 (14) | 0.4831 (2) | 0.3308 (7) | 0.051 (2) | |
C4 | 0.5553 (18) | 0.4809 (3) | 0.2231 (9) | 0.052 (3) | |
N4 | 0.3830 (15) | 0.5117 (2) | 0.2111 (7) | 0.057 (2) | |
C5 | 0.5266 (18) | 0.4463 (3) | 0.1260 (9) | 0.050 (3) | |
N5 | 0.3306 (15) | 0.4405 (3) | 0.0150 (7) | 0.062 (2) | |
O5 | 0.1513 (13) | 0.4682 (2) | −0.0022 (6) | 0.073 (2) | |
C6 | 0.7264 (19) | 0.4166 (3) | 0.1428 (9) | 0.056 (3) | |
O6 | 0.7049 (12) | 0.3841 (2) | 0.0510 (6) | 0.065 (2) | |
C67 | 0.9058 (17) | 0.3523 (3) | 0.0611 (9) | 0.060 (3) | |
C61 | 0.823 (2) | 0.3201 (3) | −0.0537 (9) | 0.061 (3) | |
C62 | 0.595 (2) | 0.3242 (3) | −0.1459 (8) | 0.063 (3) | |
C63 | 0.540 (2) | 0.2940 (3) | −0.2488 (10) | 0.067 (3) | |
C64 | 0.705 (2) | 0.2605 (3) | −0.2633 (10) | 0.069 (3) | |
C65 | 0.927 (2) | 0.2566 (3) | −0.1678 (10) | 0.071 (3) | |
C66 | 0.990 (2) | 0.2868 (3) | −0.0653 (10) | 0.070 (3) | |
C7 | 0.3879 (16) | 0.5479 (3) | 0.3068 (8) | 0.058 (3) | |
C8 | 0.1487 (16) | 0.5752 (3) | 0.2668 (8) | 0.057 (3) | |
C9 | 0.1156 (19) | 0.6117 (3) | 0.3632 (9) | 0.050 (3) | |
O91 | −0.0761 (14) | 0.6330 (2) | 0.3515 (6) | 0.073 (2) | |
O92 | 0.3289 (12) | 0.61788 (18) | 0.4604 (6) | 0.0586 (19) | |
C10 | 0.3154 (18) | 0.6550 (3) | 0.5500 (9) | 0.063 (3) | |
C11 | 0.5731 (17) | 0.6589 (3) | 0.6409 (9) | 0.073 (3) | |
H2A | 1.1446 | 0.4708 | 0.5004 | 0.071* | |
H2B | 1.2442 | 0.4299 | 0.4421 | 0.071* | |
H4 | 0.2543 | 0.5106 | 0.1400 | 0.069* | |
H67A | 0.9292 | 0.3379 | 0.1526 | 0.072* | |
H67B | 1.0721 | 0.3658 | 0.0504 | 0.072* | |
H62 | 0.4791 | 0.3472 | −0.1389 | 0.075* | |
H63 | 0.3810 | 0.2962 | −0.3126 | 0.080* | |
H64 | 0.6649 | 0.2407 | −0.3378 | 0.083* | |
H65 | 1.0384 | 0.2327 | −0.1722 | 0.085* | |
H66 | 1.1501 | 0.2847 | −0.0023 | 0.084* | |
H7A | 0.5443 | 0.5655 | 0.3048 | 0.070* | |
H7B | 0.3963 | 0.5370 | 0.4025 | 0.070* | |
H8A | 0.1504 | 0.5873 | 0.1734 | 0.068* | |
H8B | −0.0051 | 0.5563 | 0.2593 | 0.068* | |
H10A | 0.1784 | 0.6508 | 0.6065 | 0.075* | |
H10B | 0.2754 | 0.6813 | 0.4935 | 0.075* | |
H11A | 0.6083 | 0.6329 | 0.6977 | 0.110* | |
H11B | 0.5739 | 0.6839 | 0.7014 | 0.110* | |
H11C | 0.7072 | 0.6623 | 0.5835 | 0.110* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.049 (5) | 0.073 (5) | 0.034 (4) | −0.004 (4) | 0.001 (4) | −0.002 (4) |
C2 | 0.070 (8) | 0.071 (8) | 0.030 (5) | −0.005 (6) | −0.002 (6) | −0.005 (5) |
N2 | 0.052 (5) | 0.071 (5) | 0.051 (5) | 0.005 (4) | −0.001 (4) | −0.008 (4) |
N3 | 0.040 (5) | 0.072 (6) | 0.040 (4) | 0.000 (4) | 0.000 (4) | 0.000 (4) |
C4 | 0.048 (7) | 0.062 (7) | 0.045 (6) | −0.001 (5) | 0.010 (5) | −0.002 (5) |
N4 | 0.060 (6) | 0.067 (5) | 0.041 (5) | −0.001 (5) | −0.005 (4) | −0.010 (4) |
C5 | 0.048 (7) | 0.059 (6) | 0.044 (6) | −0.006 (5) | 0.008 (5) | −0.004 (5) |
N5 | 0.053 (5) | 0.081 (6) | 0.049 (5) | −0.003 (5) | 0.003 (5) | −0.003 (4) |
O5 | 0.065 (5) | 0.087 (5) | 0.059 (4) | 0.019 (4) | −0.012 (4) | −0.015 (4) |
C6 | 0.053 (7) | 0.071 (7) | 0.046 (6) | 0.000 (6) | 0.014 (6) | −0.003 (6) |
O6 | 0.067 (5) | 0.081 (5) | 0.046 (4) | 0.005 (4) | 0.002 (3) | −0.009 (4) |
C67 | 0.046 (6) | 0.072 (7) | 0.063 (7) | 0.025 (6) | 0.010 (5) | 0.011 (6) |
C61 | 0.085 (9) | 0.055 (6) | 0.042 (6) | −0.001 (6) | 0.010 (6) | −0.009 (5) |
C62 | 0.078 (9) | 0.071 (7) | 0.036 (5) | −0.001 (6) | 0.001 (6) | −0.005 (5) |
C63 | 0.067 (8) | 0.080 (7) | 0.054 (7) | −0.013 (7) | 0.013 (6) | −0.006 (6) |
C64 | 0.088 (9) | 0.073 (8) | 0.048 (6) | −0.006 (7) | 0.017 (6) | −0.012 (5) |
C65 | 0.077 (9) | 0.066 (7) | 0.072 (7) | −0.001 (6) | 0.017 (7) | −0.008 (6) |
C66 | 0.080 (9) | 0.069 (7) | 0.061 (7) | 0.011 (7) | 0.008 (6) | 0.010 (6) |
C7 | 0.045 (6) | 0.095 (8) | 0.032 (5) | 0.004 (6) | −0.001 (5) | −0.002 (5) |
C8 | 0.047 (7) | 0.076 (7) | 0.041 (5) | −0.001 (5) | −0.010 (5) | −0.009 (5) |
C9 | 0.034 (6) | 0.068 (7) | 0.048 (6) | −0.007 (5) | 0.009 (5) | 0.014 (5) |
O91 | 0.063 (5) | 0.094 (5) | 0.060 (4) | 0.012 (4) | 0.002 (4) | −0.006 (4) |
O92 | 0.051 (5) | 0.070 (4) | 0.050 (4) | −0.002 (3) | −0.004 (3) | −0.007 (3) |
C10 | 0.078 (8) | 0.052 (6) | 0.057 (6) | 0.000 (5) | 0.010 (6) | −0.007 (5) |
C11 | 0.057 (8) | 0.087 (8) | 0.070 (7) | 0.004 (6) | −0.002 (6) | −0.016 (5) |
Geometric parameters (Å, º) top
N1—C6 | 1.317 (10) | C63—C64 | 1.379 (12) |
N1—C2 | 1.368 (10) | C63—H63 | 0.9500 |
C2—N2 | 1.325 (9) | C64—C65 | 1.363 (11) |
C2—N3 | 1.351 (11) | C64—H64 | 0.9500 |
N2—H2A | 0.88 | C65—C66 | 1.374 (11) |
N2—H2B | 0.88 | C65—H65 | 0.9500 |
N3—C4 | 1.345 (9) | C66—H66 | 0.9500 |
C4—N4 | 1.310 (10) | C7—C8 | 1.508 (10) |
C4—C5 | 1.427 (11) | C7—H7A | 0.9900 |
N4—C7 | 1.464 (9) | C7—H7B | 0.9900 |
N4—H4 | 0.88 | C8—C9 | 1.507 (12) |
C5—N5 | 1.369 (9) | C8—H8A | 0.9900 |
C5—C6 | 1.386 (12) | C8—H8B | 0.9900 |
N5—O5 | 1.264 (9) | C9—O91 | 1.193 (10) |
C6—O6 | 1.346 (9) | C9—O92 | 1.348 (9) |
O6—C67 | 1.436 (9) | O92—C10 | 1.461 (9) |
C67—C61 | 1.510 (11) | C10—C11 | 1.485 (10) |
C67—H67A | 0.9900 | C10—H10A | 0.9900 |
C67—H67B | 0.9900 | C10—H10B | 0.9900 |
C61—C62 | 1.369 (11) | C11—H11A | 0.9800 |
C61—C66 | 1.378 (12) | C11—H11B | 0.9800 |
C62—C63 | 1.372 (11) | C11—H11C | 0.9800 |
C62—H62 | 0.9500 | | |
| | | |
C6—N1—C2 | 113.4 (8) | C65—C64—C63 | 118.3 (9) |
N2—C2—N3 | 117.5 (8) | C65—C64—H64 | 120.9 |
N2—C2—N1 | 112.8 (9) | C63—C64—H64 | 120.9 |
N3—C2—N1 | 129.7 (8) | C64—C65—C66 | 120.4 (10) |
C2—N2—H2A | 120.0 | C64—C65—H65 | 119.8 |
C2—N2—H2B | 120.0 | C66—C65—H65 | 119.8 |
H2A—N2—H2B | 120.0 | C65—C66—C61 | 120.1 (9) |
C4—N3—C2 | 113.6 (8) | C65—C66—H66 | 119.9 |
N4—C4—N3 | 117.2 (8) | C61—C66—H66 | 119.9 |
N4—C4—C5 | 120.3 (8) | N4—C7—C8 | 110.4 (6) |
N3—C4—C5 | 122.5 (9) | N4—C7—H7A | 109.6 |
C4—N4—C7 | 125.0 (7) | C8—C7—H7A | 109.6 |
C4—N4—H4 | 117.5 | N4—C7—H7B | 109.6 |
C7—N4—H4 | 117.5 | C8—C7—H7B | 109.6 |
N5—C5—C6 | 116.8 (9) | H7A—C7—H7B | 108.1 |
N5—C5—C4 | 127.2 (9) | C9—C8—C7 | 116.4 (7) |
C6—C5—C4 | 115.9 (8) | C9—C8—H8A | 108.2 |
O5—N5—C5 | 116.9 (8) | C7—C8—H8A | 108.2 |
N1—C6—O6 | 118.3 (9) | C9—C8—H8B | 108.2 |
N1—C6—C5 | 124.7 (9) | C7—C8—H8B | 108.2 |
O6—C6—C5 | 116.9 (8) | H8A—C8—H8B | 107.3 |
C6—O6—C67 | 120.0 (7) | O91—C9—O92 | 124.5 (9) |
O6—C67—C61 | 107.2 (7) | O91—C9—C8 | 123.3 (8) |
O6—C67—H67A | 110.3 | O92—C9—C8 | 112.2 (8) |
C61—C67—H67A | 110.3 | C9—O92—C10 | 114.6 (7) |
O6—C67—H67B | 110.3 | O92—C10—C11 | 106.8 (7) |
C61—C67—H67B | 110.3 | O92—C10—H10A | 110.4 |
H67A—C67—H67B | 108.5 | C11—C10—H10A | 110.4 |
C62—C61—C66 | 120.6 (9) | O92—C10—H10B | 110.4 |
C62—C61—C67 | 122.1 (9) | C11—C10—H10B | 110.4 |
C66—C61—C67 | 117.2 (9) | H10A—C10—H10B | 108.6 |
C61—C62—C63 | 117.9 (10) | C10—C11—H11A | 109.5 |
C61—C62—H62 | 121.1 | C10—C11—H11B | 109.5 |
C63—C62—H62 | 121.1 | H11A—C11—H11B | 109.5 |
C62—C63—C64 | 122.7 (9) | C10—C11—H11C | 109.5 |
C62—C63—H63 | 118.7 | H11A—C11—H11C | 109.5 |
C64—C63—H63 | 118.7 | H11B—C11—H11C | 109.5 |
| | | |
C6—N1—C2—N2 | 179.4 (8) | N1—C6—O6—C67 | −4.0 (12) |
C6—N1—C2—N3 | 0.5 (14) | C5—C6—O6—C67 | 179.4 (9) |
N2—C2—N3—C4 | −179.5 (8) | C6—O6—C67—C61 | 179.0 (8) |
N1—C2—N3—C4 | −0.7 (14) | O6—C67—C61—C62 | 0.9 (13) |
C2—N3—C4—N4 | −178.2 (9) | O6—C67—C61—C66 | 178.9 (9) |
C2—N3—C4—C5 | 2.8 (13) | C66—C61—C62—C63 | 0.4 (15) |
N3—C4—N4—C7 | −1.1 (14) | C67—C61—C62—C63 | 178.4 (9) |
C5—C4—N4—C7 | 177.9 (8) | C61—C62—C63—C64 | −0.9 (15) |
N4—C4—C5—N5 | −0.2 (15) | C62—C63—C64—C65 | 2.7 (16) |
N3—C4—C5—N5 | 178.7 (9) | C63—C64—C65—C66 | −3.9 (16) |
N4—C4—C5—C6 | 176.4 (9) | C64—C65—C66—C61 | 3.5 (16) |
N3—C4—C5—C6 | −4.6 (14) | C62—C61—C66—C65 | −1.7 (16) |
C6—C5—N5—O5 | −178.4 (9) | C67—C61—C66—C65 | −179.8 (9) |
C4—C5—N5—O5 | −1.8 (14) | C4—N4—C7—C8 | −175.7 (9) |
C2—N1—C6—O6 | −178.9 (8) | N4—C7—C8—C9 | 175.0 (8) |
C2—N1—C6—C5 | −2.6 (14) | C7—C8—C9—O91 | −172.2 (9) |
N5—C5—C6—N1 | −178.4 (8) | C7—C8—C9—O92 | 9.4 (12) |
C4—C5—C6—N1 | 4.5 (15) | O91—C9—O92—C10 | −3.0 (13) |
N5—C5—C6—O6 | −2.1 (13) | C8—C9—O92—C10 | 175.3 (7) |
C4—C5—C6—O6 | −179.1 (8) | C9—O92—C10—C11 | −175.1 (8) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O5 | 0.88 | 1.93 | 2.603 (9) | 133 |
N4—H4···O5i | 0.88 | 2.40 | 3.223 (10) | 156 |
N2—H2A···N3ii | 0.88 | 2.18 | 3.056 (9) | 171 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+2, −y+1, −z+1. |
(5B) Ethyl
N-(2-amino-6-benzyloxo-5-nitrosopyrimidin-4-yl)-
β-alaninate
top
Crystal data top
C16H19N5O4 | F(000) = 728 |
Mr = 345.36 | Dx = 1.364 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.4830 (2) Å | Cell parameters from 8888 reflections |
b = 16.6110 (6) Å | θ = 1.0–27.5° |
c = 13.5378 (6) Å | µ = 0.10 mm−1 |
β = 91.5420 (11)° | T = 150 K |
V = 1682.14 (11) Å3 | Needle, pink |
Z = 4 | 0.50 × 0.20 × 0.18 mm |
Data collection top
Kappa-CCD diffractometer | 2992 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2487 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.083 |
φ scans, and ω scans with κ offsets | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −8→8 |
Tmin = 0.951, Tmax = 0.982 | k = −19→19 |
19365 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.1159P)2] where P = (Fo2 + 2Fc2)/3 |
2992 reflections | (Δ/σ)max = 0.004 |
453 parameters | Δρmax = 0.56 e Å−3 |
1 restraint | Δρmin = −0.33 e Å−3 |
Special details top
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm
[Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which
effectively corrects for absorption effects. High redundancy data were used in
the scaling program hence the 'multi-scan' code word was used. No transmission
coefficients are available from the program (only scale factors for each
frame). The scale factors in the experimental table are calculated from the
'size' command in the SHELXL97 input file. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N11 | 1.0633 (4) | 0.0120 (2) | 0.2019 (2) | 0.0291 (8) | |
C110 | 0.7109 (8) | −0.0180 (5) | 0.7469 (4) | 0.0727 (18) | |
C111 | 0.5954 (8) | −0.0804 (4) | 0.7052 (4) | 0.0673 (17) | |
C12 | 1.2030 (5) | 0.0057 (2) | 0.2705 (3) | 0.0285 (9) | |
N12 | 1.3640 (4) | 0.0108 (3) | 0.2344 (3) | 0.0379 (9) | |
N13 | 1.1903 (4) | −0.0061 (2) | 0.3681 (2) | 0.0294 (8) | |
N14 | 1.0080 (5) | −0.0300 (2) | 0.4985 (3) | 0.0345 (8) | |
C14 | 1.0259 (5) | −0.0147 (2) | 0.4028 (3) | 0.0272 (9) | |
C15 | 0.8686 (5) | −0.0083 (2) | 0.3396 (3) | 0.0246 (9) | |
N15 | 0.6965 (4) | −0.0158 (2) | 0.3646 (2) | 0.0279 (8) | |
O15 | 0.6638 (3) | −0.03154 (18) | 0.4547 (2) | 0.0322 (7) | |
C16 | 0.9037 (5) | 0.0051 (2) | 0.2372 (3) | 0.0251 (9) | |
C161 | 0.6164 (5) | −0.0028 (3) | 0.0197 (3) | 0.0271 (9) | |
C162 | 0.5734 (5) | −0.0806 (3) | −0.0081 (3) | 0.0334 (10) | |
C163 | 0.4066 (6) | −0.0975 (3) | −0.0512 (3) | 0.0429 (12) | |
C164 | 0.2853 (6) | −0.0371 (4) | −0.0685 (3) | 0.0472 (13) | |
C165 | 0.3277 (6) | 0.0416 (4) | −0.0419 (3) | 0.0467 (13) | |
C166 | 0.4949 (6) | 0.0587 (3) | 0.0012 (3) | 0.0335 (10) | |
C167 | 0.7930 (5) | 0.0145 (3) | 0.0705 (3) | 0.0307 (10) | |
O16 | 0.7601 (3) | 0.00849 (17) | 0.17628 (19) | 0.0286 (7) | |
C17 | 1.1556 (5) | −0.0369 (3) | 0.5703 (3) | 0.0371 (11) | |
C18 | 1.1562 (6) | 0.0310 (3) | 0.6449 (3) | 0.0475 (12) | |
C19 | 0.9996 (6) | 0.0369 (3) | 0.7105 (4) | 0.0502 (13) | |
O191 | 0.9810 (6) | 0.0871 (4) | 0.7716 (4) | 0.0957 (19) | |
O192 | 0.8763 (5) | −0.0215 (2) | 0.6912 (2) | 0.0585 (10) | |
N21 | −0.0683 (4) | 0.2105 (2) | 0.2997 (2) | 0.0321 (8) | |
C210 | 0.3345 (7) | 0.2998 (4) | −0.2190 (4) | 0.0640 (16) | |
C211 | 0.4022 (7) | 0.2158 (4) | −0.2139 (4) | 0.0552 (13) | |
C22 | −0.2057 (5) | 0.2146 (3) | 0.2309 (3) | 0.0279 (9) | |
N22 | −0.3680 (4) | 0.2106 (3) | 0.2679 (3) | 0.0395 (9) | |
N23 | −0.1934 (4) | 0.2217 (2) | 0.1332 (3) | 0.0288 (8) | |
C24 | −0.0286 (5) | 0.2268 (2) | 0.0973 (3) | 0.0245 (8) | |
N24 | −0.0080 (4) | 0.2340 (2) | 0.0012 (3) | 0.0277 (8) | |
C25 | 0.1287 (5) | 0.2231 (3) | 0.1621 (3) | 0.0258 (8) | |
N25 | 0.3010 (4) | 0.2253 (2) | 0.1362 (2) | 0.0292 (8) | |
O25 | 0.3347 (3) | 0.23345 (19) | 0.0449 (2) | 0.0340 (7) | |
C26 | 0.0915 (5) | 0.2143 (3) | 0.2643 (3) | 0.0274 (9) | |
C261 | 0.3809 (5) | 0.2102 (3) | 0.4828 (3) | 0.0291 (9) | |
C262 | 0.4865 (6) | 0.1424 (3) | 0.4901 (3) | 0.0324 (10) | |
C263 | 0.6565 (6) | 0.1482 (3) | 0.5330 (3) | 0.0397 (11) | |
C264 | 0.7225 (6) | 0.2200 (4) | 0.5661 (3) | 0.0458 (12) | |
C265 | 0.6170 (7) | 0.2881 (4) | 0.5601 (3) | 0.0488 (14) | |
C266 | 0.4473 (6) | 0.2836 (3) | 0.5169 (3) | 0.0399 (11) | |
C267 | 0.2017 (5) | 0.2063 (3) | 0.4317 (3) | 0.0351 (10) | |
O26 | 0.2338 (3) | 0.2118 (2) | 0.32645 (19) | 0.0321 (7) | |
C27 | −0.1533 (5) | 0.2377 (3) | −0.0735 (3) | 0.0324 (10) | |
C28 | −0.1392 (5) | 0.3107 (3) | −0.1401 (3) | 0.0394 (10) | |
C29 | 0.0143 (5) | 0.3083 (3) | −0.2087 (3) | 0.0368 (10) | |
O291 | 0.0006 (5) | 0.3144 (3) | −0.2967 (3) | 0.0664 (12) | |
O292 | 0.1711 (4) | 0.3057 (3) | −0.1607 (2) | 0.0577 (10) | |
H11A | 0.7361 | −0.0281 | 0.8180 | 0.087* | |
H11B | 0.6539 | 0.0356 | 0.7396 | 0.087* | |
H11C | 0.5644 | −0.0673 | 0.6363 | 0.101* | |
H11D | 0.4860 | −0.0838 | 0.7432 | 0.101* | |
H11E | 0.6578 | −0.1323 | 0.7081 | 0.101* | |
H12A | 1.4587 | 0.0064 | 0.2740 | 0.045* | |
H12B | 1.3771 | 0.0186 | 0.1707 | 0.045* | |
H14 | 0.8989 | −0.0363 | 0.5200 | 0.041* | |
H162 | 0.6578 | −0.1226 | 0.0022 | 0.040* | |
H163 | 0.3768 | −0.1513 | −0.0687 | 0.052* | |
H164 | 0.1722 | −0.0489 | −0.0987 | 0.057* | |
H165 | 0.2432 | 0.0835 | −0.0530 | 0.056* | |
H166 | 0.5254 | 0.1126 | 0.0180 | 0.040* | |
H16A | 0.8840 | −0.0253 | 0.0509 | 0.037* | |
H16B | 0.8354 | 0.0691 | 0.0536 | 0.037* | |
H17A | 1.2699 | −0.0366 | 0.5352 | 0.045* | |
H17B | 1.1464 | −0.0890 | 0.6054 | 0.045* | |
H18A | 1.2653 | 0.0257 | 0.6874 | 0.057* | |
H18B | 1.1658 | 0.0824 | 0.6085 | 0.057* | |
H21A | 0.4265 | 0.3373 | −0.1922 | 0.077* | |
H21B | 0.3073 | 0.3147 | −0.2886 | 0.077* | |
H21C | 0.4244 | 0.2007 | −0.1447 | 0.083* | |
H21D | 0.5138 | 0.2119 | −0.2499 | 0.083* | |
H21E | 0.3131 | 0.1794 | −0.2438 | 0.083* | |
H22A | −0.4630 | 0.2126 | 0.2282 | 0.047* | |
H22B | −0.3805 | 0.2059 | 0.3321 | 0.047* | |
H24 | 0.1022 | 0.2367 | −0.0198 | 0.033* | |
H262 | 0.4432 | 0.0921 | 0.4661 | 0.039* | |
H263 | 0.7283 | 0.1012 | 0.5393 | 0.048* | |
H264 | 0.8406 | 0.2232 | 0.5933 | 0.055* | |
H265 | 0.6607 | 0.3379 | 0.5854 | 0.059* | |
H266 | 0.3762 | 0.3308 | 0.5105 | 0.048* | |
H26A | 0.1412 | 0.1550 | 0.4471 | 0.042* | |
H26B | 0.1253 | 0.2514 | 0.4530 | 0.042* | |
H27A | −0.2692 | 0.2392 | −0.0400 | 0.039* | |
H27B | −0.1511 | 0.1883 | −0.1144 | 0.039* | |
H28A | −0.2516 | 0.3158 | −0.1799 | 0.047* | |
H28B | −0.1275 | 0.3594 | −0.0982 | 0.047* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N11 | 0.0231 (18) | 0.037 (2) | 0.027 (2) | −0.0009 (14) | −0.0014 (13) | 0.0005 (16) |
C110 | 0.075 (4) | 0.102 (5) | 0.042 (3) | −0.016 (4) | 0.032 (3) | −0.016 (3) |
C111 | 0.067 (3) | 0.091 (5) | 0.045 (3) | 0.001 (3) | 0.016 (3) | 0.003 (3) |
C12 | 0.028 (2) | 0.026 (2) | 0.031 (2) | −0.0016 (16) | 0.0044 (17) | −0.0003 (18) |
N12 | 0.0261 (19) | 0.060 (3) | 0.028 (2) | −0.0050 (16) | 0.0040 (14) | −0.0015 (18) |
N13 | 0.0278 (18) | 0.040 (2) | 0.0207 (19) | −0.0023 (14) | 0.0008 (13) | −0.0038 (15) |
N14 | 0.0308 (17) | 0.049 (2) | 0.0235 (19) | 0.0007 (15) | 0.0009 (12) | −0.0005 (17) |
C14 | 0.029 (2) | 0.026 (2) | 0.027 (2) | −0.0022 (16) | 0.0014 (16) | −0.0061 (18) |
C15 | 0.020 (2) | 0.029 (2) | 0.024 (2) | 0.0009 (15) | 0.0028 (15) | −0.0010 (17) |
N15 | 0.0297 (19) | 0.0275 (19) | 0.027 (2) | −0.0030 (14) | 0.0065 (13) | −0.0037 (15) |
O15 | 0.0314 (15) | 0.0401 (18) | 0.0257 (17) | −0.0042 (12) | 0.0087 (11) | 0.0007 (13) |
C16 | 0.020 (2) | 0.026 (2) | 0.029 (2) | −0.0004 (15) | −0.0010 (15) | −0.0030 (18) |
C161 | 0.029 (2) | 0.035 (2) | 0.018 (2) | −0.0007 (17) | 0.0054 (16) | 0.0023 (17) |
C162 | 0.042 (2) | 0.030 (2) | 0.028 (2) | −0.0002 (18) | 0.0008 (18) | −0.0021 (19) |
C163 | 0.050 (3) | 0.047 (3) | 0.032 (3) | −0.016 (2) | 0.0030 (19) | 0.000 (2) |
C164 | 0.037 (3) | 0.074 (4) | 0.030 (3) | −0.012 (2) | −0.0044 (19) | 0.007 (2) |
C165 | 0.038 (3) | 0.061 (3) | 0.041 (3) | 0.004 (2) | −0.001 (2) | 0.018 (3) |
C166 | 0.034 (2) | 0.036 (2) | 0.030 (2) | 0.0006 (17) | 0.0035 (16) | 0.0045 (19) |
C167 | 0.033 (2) | 0.039 (2) | 0.021 (2) | −0.0047 (17) | 0.0045 (15) | 0.0007 (19) |
O16 | 0.0241 (14) | 0.0408 (17) | 0.0210 (15) | 0.0017 (11) | 0.0009 (10) | 0.0000 (13) |
C17 | 0.031 (2) | 0.058 (3) | 0.023 (2) | 0.0034 (19) | −0.0031 (17) | 0.002 (2) |
C18 | 0.046 (3) | 0.060 (3) | 0.036 (3) | −0.004 (2) | −0.0037 (19) | −0.001 (2) |
C19 | 0.053 (3) | 0.060 (3) | 0.037 (3) | 0.008 (2) | −0.010 (2) | −0.011 (3) |
O191 | 0.073 (3) | 0.115 (5) | 0.098 (4) | 0.006 (3) | 0.002 (2) | −0.069 (4) |
O192 | 0.062 (2) | 0.075 (3) | 0.040 (2) | −0.0073 (19) | 0.0167 (16) | −0.0088 (18) |
N21 | 0.0221 (17) | 0.044 (2) | 0.030 (2) | 0.0027 (15) | 0.0043 (13) | 0.0073 (17) |
C210 | 0.057 (3) | 0.084 (4) | 0.052 (3) | 0.011 (3) | 0.026 (2) | 0.015 (3) |
C211 | 0.052 (3) | 0.061 (3) | 0.054 (3) | −0.004 (3) | 0.019 (2) | −0.004 (3) |
C22 | 0.025 (2) | 0.035 (2) | 0.024 (2) | 0.0026 (18) | −0.0008 (15) | 0.0044 (19) |
N22 | 0.0226 (18) | 0.068 (3) | 0.028 (2) | 0.0045 (17) | 0.0027 (13) | 0.009 (2) |
N23 | 0.0184 (17) | 0.032 (2) | 0.036 (2) | 0.0000 (14) | 0.0015 (13) | 0.0053 (16) |
C24 | 0.025 (2) | 0.022 (2) | 0.026 (2) | 0.0003 (16) | −0.0004 (15) | 0.0037 (17) |
N24 | 0.0183 (15) | 0.038 (2) | 0.0267 (18) | −0.0018 (13) | −0.0011 (12) | 0.0042 (16) |
C25 | 0.022 (2) | 0.026 (2) | 0.029 (2) | −0.0010 (17) | −0.0009 (15) | 0.0009 (18) |
N25 | 0.0265 (18) | 0.033 (2) | 0.028 (2) | 0.0011 (15) | 0.0012 (13) | 0.0034 (16) |
O25 | 0.0270 (15) | 0.048 (2) | 0.0275 (17) | −0.0005 (12) | 0.0033 (11) | 0.0066 (14) |
C26 | 0.026 (2) | 0.031 (2) | 0.025 (2) | 0.0023 (18) | −0.0012 (15) | 0.0045 (19) |
C261 | 0.029 (2) | 0.039 (3) | 0.020 (2) | 0.0020 (18) | 0.0042 (16) | 0.0019 (19) |
C262 | 0.038 (2) | 0.034 (2) | 0.025 (2) | −0.0031 (17) | 0.0002 (17) | −0.0030 (19) |
C263 | 0.030 (2) | 0.051 (3) | 0.037 (3) | 0.0070 (19) | −0.0027 (18) | −0.003 (2) |
C264 | 0.036 (2) | 0.068 (3) | 0.033 (3) | −0.012 (3) | −0.0042 (18) | −0.003 (3) |
C265 | 0.064 (3) | 0.056 (3) | 0.026 (3) | −0.027 (3) | 0.000 (2) | −0.007 (2) |
C266 | 0.054 (3) | 0.037 (3) | 0.029 (3) | 0.001 (2) | 0.0051 (19) | 0.000 (2) |
C267 | 0.030 (2) | 0.052 (3) | 0.023 (2) | 0.0076 (19) | −0.0005 (16) | 0.003 (2) |
O26 | 0.0209 (14) | 0.0511 (18) | 0.0240 (16) | 0.0019 (13) | −0.0019 (10) | 0.0034 (14) |
C27 | 0.025 (2) | 0.039 (3) | 0.033 (3) | −0.0006 (16) | −0.0029 (16) | −0.0007 (19) |
C28 | 0.026 (2) | 0.049 (3) | 0.043 (3) | −0.0013 (18) | −0.0104 (16) | 0.008 (2) |
C29 | 0.040 (2) | 0.044 (3) | 0.026 (2) | −0.0092 (19) | −0.0082 (17) | 0.005 (2) |
O291 | 0.075 (3) | 0.092 (3) | 0.031 (2) | −0.035 (2) | −0.0116 (16) | 0.0106 (19) |
O292 | 0.0359 (17) | 0.103 (3) | 0.0350 (19) | 0.0141 (18) | 0.0091 (13) | 0.013 (2) |
Geometric parameters (Å, º) top
N11—C16 | 1.304 (5) | N21—C26 | 1.301 (5) |
N11—C12 | 1.383 (5) | N21—C22 | 1.371 (5) |
C110—C111 | 1.455 (9) | C210—O292 | 1.477 (5) |
C110—O192 | 1.468 (6) | C210—C211 | 1.485 (9) |
C110—H11A | 0.9900 | C210—H21A | 0.9900 |
C110—H11B | 0.9900 | C210—H21B | 0.9900 |
C111—H11C | 0.9800 | C211—H21C | 0.9800 |
C111—H11D | 0.9800 | C211—H21D | 0.9800 |
C111—H11E | 0.9800 | C211—H21E | 0.9800 |
C12—N12 | 1.314 (5) | C22—N22 | 1.327 (5) |
C12—N13 | 1.342 (5) | C22—N23 | 1.333 (5) |
N12—H12A | 0.8800 | N22—H22A | 0.8800 |
N12—H12B | 0.8800 | N22—H22B | 0.8800 |
N13—C14 | 1.336 (5) | N23—C24 | 1.340 (5) |
N14—C14 | 1.330 (6) | C24—N24 | 1.320 (5) |
N14—C17 | 1.456 (5) | C24—C25 | 1.450 (5) |
N14—H14 | 0.8800 | N24—C27 | 1.466 (5) |
C14—C15 | 1.441 (5) | N24—H24 | 0.8800 |
C15—N15 | 1.346 (5) | C25—N25 | 1.345 (5) |
C15—C16 | 1.435 (6) | C25—C26 | 1.427 (5) |
N15—O15 | 1.277 (4) | N25—O25 | 1.276 (4) |
C16—O16 | 1.338 (4) | C26—O26 | 1.340 (4) |
C161—C162 | 1.381 (6) | C261—C262 | 1.378 (6) |
C161—C166 | 1.386 (6) | C261—C266 | 1.391 (7) |
C161—C167 | 1.500 (5) | C261—C267 | 1.494 (5) |
C162—C163 | 1.392 (6) | C262—C263 | 1.388 (6) |
C162—H162 | 0.9500 | C262—H262 | 0.9500 |
C163—C164 | 1.369 (7) | C263—C264 | 1.362 (7) |
C163—H163 | 0.9500 | C263—H263 | 0.9500 |
C164—C165 | 1.390 (8) | C264—C265 | 1.380 (8) |
C164—H164 | 0.9500 | C264—H264 | 0.9500 |
C165—C166 | 1.395 (6) | C265—C266 | 1.386 (7) |
C165—H165 | 0.9500 | C265—H265 | 0.9500 |
C166—H166 | 0.9500 | C266—H266 | 0.9500 |
C167—O16 | 1.463 (5) | C267—O26 | 1.454 (5) |
C167—H16A | 0.9900 | C267—H26A | 0.9900 |
C167—H16B | 0.9900 | C267—H26B | 0.9900 |
C17—C18 | 1.514 (7) | C27—C28 | 1.517 (6) |
C17—H17A | 0.9900 | C27—H27A | 0.9900 |
C17—H17B | 0.9900 | C27—H27B | 0.9900 |
C18—C19 | 1.492 (6) | C28—C29 | 1.498 (6) |
C18—H18A | 0.9900 | C28—H28A | 0.9900 |
C18—H18B | 0.9900 | C28—H28B | 0.9900 |
C19—O191 | 1.185 (6) | C29—O291 | 1.197 (5) |
C19—O192 | 1.359 (6) | C29—O292 | 1.326 (5) |
| | | |
C16—N11—C12 | 115.5 (3) | C26—N21—C22 | 115.3 (3) |
C111—C110—O192 | 105.8 (5) | O292—C210—C211 | 108.9 (5) |
C111—C110—H11A | 110.6 | O292—C210—H21A | 109.9 |
O192—C110—H11A | 110.6 | C211—C210—H21A | 109.9 |
C111—C110—H11B | 110.6 | O292—C210—H21B | 109.9 |
O192—C110—H11B | 110.6 | C211—C210—H21B | 109.9 |
H11A—C110—H11B | 108.7 | H21A—C210—H21B | 108.3 |
C110—C111—H11C | 109.5 | C210—C211—H21C | 109.5 |
C110—C111—H11D | 109.5 | C210—C211—H21D | 109.5 |
H11C—C111—H11D | 109.5 | H21C—C211—H21D | 109.5 |
C110—C111—H11E | 109.5 | C210—C211—H21E | 109.5 |
H11C—C111—H11E | 109.5 | H21C—C211—H21E | 109.5 |
H11D—C111—H11E | 109.5 | H21D—C211—H21E | 109.5 |
N12—C12—N13 | 117.7 (4) | N22—C22—N23 | 117.8 (3) |
N12—C12—N11 | 115.5 (4) | N22—C22—N21 | 114.7 (3) |
N13—C12—N11 | 126.8 (3) | N23—C22—N21 | 127.4 (3) |
C12—N12—H12A | 120.0 | C22—N22—H22A | 120.0 |
C12—N12—H12B | 120.0 | C22—N22—H22B | 120.0 |
H12A—N12—H12B | 120.0 | H22A—N22—H22B | 120.0 |
C14—N13—C12 | 116.9 (3) | C22—N23—C24 | 117.0 (3) |
C14—N14—C17 | 124.8 (3) | N24—C24—N23 | 119.8 (3) |
C14—N14—H14 | 117.6 | N24—C24—C25 | 119.0 (3) |
C17—N14—H14 | 117.6 | N23—C24—C25 | 121.2 (4) |
N14—C14—N13 | 118.7 (4) | C24—N24—C27 | 125.4 (3) |
N14—C14—C15 | 119.4 (3) | C24—N24—H24 | 117.3 |
N13—C14—C15 | 121.9 (4) | C27—N24—H24 | 117.3 |
N15—C15—C16 | 117.3 (3) | N25—C25—C26 | 117.9 (3) |
N15—C15—C14 | 128.0 (4) | N25—C25—C24 | 127.6 (4) |
C16—C15—C14 | 114.7 (3) | C26—C25—C24 | 114.5 (3) |
O15—N15—C15 | 118.0 (3) | O25—N25—C25 | 118.1 (3) |
N11—C16—O16 | 120.0 (4) | N21—C26—O26 | 119.3 (3) |
N11—C16—C15 | 124.1 (3) | N21—C26—C25 | 124.6 (3) |
O16—C16—C15 | 115.9 (3) | O26—C26—C25 | 116.1 (3) |
C162—C161—C166 | 119.5 (4) | C262—C261—C266 | 119.6 (4) |
C162—C161—C167 | 120.0 (4) | C262—C261—C267 | 120.3 (4) |
C166—C161—C167 | 120.5 (4) | C266—C261—C267 | 120.0 (4) |
C161—C162—C163 | 120.2 (4) | C261—C262—C263 | 119.4 (4) |
C161—C162—H162 | 119.9 | C261—C262—H262 | 120.3 |
C163—C162—H162 | 119.9 | C263—C262—H262 | 120.3 |
C164—C163—C162 | 120.4 (5) | C264—C263—C262 | 121.2 (4) |
C164—C163—H163 | 119.8 | C264—C263—H263 | 119.4 |
C162—C163—H163 | 119.8 | C262—C263—H263 | 119.4 |
C163—C164—C165 | 119.9 (4) | C263—C264—C265 | 119.8 (4) |
C163—C164—H164 | 120.0 | C263—C264—H264 | 120.1 |
C165—C164—H164 | 120.0 | C265—C264—H264 | 120.1 |
C164—C165—C166 | 119.7 (5) | C264—C265—C266 | 119.8 (5) |
C164—C165—H165 | 120.1 | C264—C265—H265 | 120.1 |
C166—C165—H165 | 120.1 | C266—C265—H265 | 120.1 |
C161—C166—C165 | 120.1 (4) | C265—C266—C261 | 120.2 (4) |
C161—C166—H166 | 119.9 | C265—C266—H266 | 119.9 |
C165—C166—H166 | 119.9 | C261—C266—H266 | 119.9 |
O16—C167—C161 | 105.4 (3) | O26—C267—C261 | 106.4 (3) |
O16—C167—H16A | 110.7 | O26—C267—H26A | 110.5 |
C161—C167—H16A | 110.7 | C261—C267—H26A | 110.5 |
O16—C167—H16B | 110.7 | O26—C267—H26B | 110.5 |
C161—C167—H16B | 110.7 | C261—C267—H26B | 110.5 |
H16A—C167—H16B | 108.8 | H26A—C267—H26B | 108.6 |
C16—O16—C167 | 116.9 (3) | C26—O26—C267 | 117.9 (3) |
N14—C17—C18 | 112.0 (4) | N24—C27—C28 | 112.4 (3) |
N14—C17—H17A | 109.2 | N24—C27—H27A | 109.1 |
C18—C17—H17A | 109.2 | C28—C27—H27A | 109.1 |
N14—C17—H17B | 109.2 | N24—C27—H27B | 109.1 |
C18—C17—H17B | 109.2 | C28—C27—H27B | 109.1 |
H17A—C17—H17B | 107.9 | H27A—C27—H27B | 107.9 |
C19—C18—C17 | 117.2 (4) | C29—C28—C27 | 114.4 (4) |
C19—C18—H18A | 108.0 | C29—C28—H28A | 108.7 |
C17—C18—H18A | 108.0 | C27—C28—H28A | 108.6 |
C19—C18—H18B | 108.0 | C29—C28—H28B | 108.6 |
C17—C18—H18B | 108.0 | C27—C28—H28B | 108.6 |
H18A—C18—H18B | 107.2 | H28A—C28—H28B | 107.6 |
O191—C19—O192 | 123.0 (5) | O291—C29—O292 | 122.8 (4) |
O191—C19—C18 | 124.7 (5) | O291—C29—C28 | 124.6 (4) |
O192—C19—C18 | 112.3 (4) | O292—C29—C28 | 112.3 (3) |
C19—O192—C110 | 116.8 (4) | C29—O292—C210 | 118.3 (4) |
| | | |
C16—N11—C12—N12 | 178.5 (4) | C26—N21—C22—N22 | 179.9 (4) |
C16—N11—C12—N13 | −0.3 (6) | C26—N21—C22—N23 | 0.4 (7) |
N12—C12—N13—C14 | −177.1 (4) | N22—C22—N23—C24 | 179.1 (4) |
N11—C12—N13—C14 | 1.6 (6) | N21—C22—N23—C24 | −1.3 (7) |
C17—N14—C14—N13 | 1.1 (6) | C22—N23—C24—N24 | −179.9 (4) |
C17—N14—C14—C15 | −179.2 (4) | C22—N23—C24—C25 | 1.3 (6) |
C12—N13—C14—N14 | 177.2 (4) | N23—C24—N24—C27 | 0.6 (6) |
C12—N13—C14—C15 | −2.5 (6) | C25—C24—N24—C27 | 179.4 (4) |
N14—C14—C15—N15 | 0.2 (6) | N24—C24—C25—N25 | −0.7 (6) |
N13—C14—C15—N15 | 179.8 (4) | N23—C24—C25—N25 | 178.1 (4) |
N14—C14—C15—C16 | −177.6 (4) | N24—C24—C25—C26 | −179.2 (4) |
N13—C14—C15—C16 | 2.0 (5) | N23—C24—C25—C26 | −0.4 (6) |
C16—C15—N15—O15 | 176.7 (4) | C26—C25—N25—O25 | −179.8 (4) |
C14—C15—N15—O15 | −1.0 (6) | C24—C25—N25—O25 | 1.8 (6) |
C12—N11—C16—O16 | −178.5 (3) | C22—N21—C26—O26 | 179.1 (4) |
C12—N11—C16—C15 | −0.2 (6) | C22—N21—C26—C25 | 0.7 (6) |
N15—C15—C16—N11 | −178.6 (4) | N25—C25—C26—N21 | −179.3 (4) |
C14—C15—C16—N11 | −0.6 (6) | C24—C25—C26—N21 | −0.7 (6) |
N15—C15—C16—O16 | −0.2 (5) | N25—C25—C26—O26 | 2.3 (6) |
C14—C15—C16—O16 | 177.8 (3) | C24—C25—C26—O26 | −179.1 (4) |
C166—C161—C162—C163 | −2.3 (6) | C266—C261—C262—C263 | 1.1 (6) |
C167—C161—C162—C163 | 177.1 (4) | C267—C261—C262—C263 | 176.4 (4) |
C161—C162—C163—C164 | 1.5 (7) | C261—C262—C263—C264 | −1.3 (7) |
C162—C163—C164—C165 | −0.8 (7) | C262—C263—C264—C265 | 2.0 (7) |
C163—C164—C165—C166 | 0.8 (7) | C263—C264—C265—C266 | −2.5 (7) |
C162—C161—C166—C165 | 2.3 (7) | C264—C265—C266—C261 | 2.3 (7) |
C167—C161—C166—C165 | −177.0 (4) | C262—C261—C266—C265 | −1.6 (6) |
C164—C165—C166—C161 | −1.6 (7) | C267—C261—C266—C265 | −176.9 (4) |
C162—C161—C167—O16 | −91.8 (4) | C262—C261—C267—O26 | −81.0 (5) |
C166—C161—C167—O16 | 87.6 (4) | C266—C261—C267—O26 | 94.2 (5) |
N11—C16—O16—C167 | 4.1 (5) | N21—C26—O26—C267 | −1.1 (6) |
C15—C16—O16—C167 | −174.4 (3) | C25—C26—O26—C267 | 177.5 (4) |
C161—C167—O16—C16 | 166.7 (3) | C261—C267—O26—C26 | −176.2 (4) |
C14—N14—C17—C18 | 112.8 (5) | C24—N24—C27—C28 | 126.5 (4) |
N14—C17—C18—C19 | 63.1 (5) | N24—C27—C28—C29 | 69.2 (5) |
C17—C18—C19—O191 | −179.3 (6) | C27—C28—C29—O291 | 123.9 (5) |
C17—C18—C19—O192 | −0.6 (6) | C27—C28—C29—O292 | −61.7 (5) |
O191—C19—O192—C110 | 2.8 (8) | O291—C29—O292—C210 | −8.0 (7) |
C18—C19—O192—C110 | −175.9 (5) | C28—C29—O292—C210 | 177.6 (5) |
C111—C110—O192—C19 | 173.8 (5) | C211—C210—O292—C29 | −103.5 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N14—H14···O15 | 0.88 | 1.95 | 2.628 (4) | 133 |
N24—H24···O25 | 0.88 | 1.93 | 2.616 (4) | 134 |
N12—H12A···N15i | 0.88 | 2.17 | 3.042 (5) | 174 |
N22—H22A···N25ii | 0.88 | 2.14 | 3.023 (4) | 176 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
(6) Ethyl
N-(2-amino-6-benzyloxy-5-nitrosopyrimidin-4-yl)-
L-phenylalaninate
top
Crystal data top
C22H23N5O4 | Z = 2 |
Mr = 421.45 | F(000) = 444 |
Triclinic, P1 | Dx = 1.338 Mg m−3 |
a = 7.9899 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.4278 (3) Å | Cell parameters from 14344 reflections |
c = 17.0042 (7) Å | θ = 2.9–27.5° |
α = 99.9100 (12)° | µ = 0.10 mm−1 |
β = 90.5610 (13)° | T = 150 K |
γ = 111.4880 (17)° | Plate, pink |
V = 1046.22 (7) Å3 | 0.30 × 0.20 × 0.03 mm |
Data collection top
Kappa-CCD diffractometer | 8664 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 6321 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
φ scans and ω scans with κ offsets | θmax = 27.5°, θmin = 2.9° |
Absorption correction: multi-scan Sortav (Blessing, 1995 & 1997) | h = −10→10 |
Tmin = 0.972, Tmax = 0.997 | k = −10→10 |
14846 measured reflections | l = −22→22 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0638P)2] where P = (Fo2 + 2Fc2)/3 |
4686 reflections | (Δ/σ)max < 0.001 |
561 parameters | Δρmax = 0.20 e Å−3 |
3 restraints | Δρmin = −0.24 e Å−3 |
Special details top
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm
[Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which
effectively corrects for absorption effects. High redundancy data were used in
the scaling program hence the 'multi-scan' code word was used. No transmission
coefficients are available from the program (only scale factors for each
frame). The scale factors in the experimental table are calculated from the
'size' command in the SHELXL97 input file. |
Geometry. Mean-plane data from the final SHELXL97 refinement run:- |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N11 | 0.0293 (3) | −0.2813 (3) | 0.02734 (15) | 0.0246 (5) | |
C12 | 0.1004 (4) | −0.3196 (4) | 0.09199 (17) | 0.0237 (6) | |
N12 | 0.0819 (4) | −0.4846 (3) | 0.08480 (16) | 0.0293 (6) | |
N13 | 0.1826 (3) | −0.2111 (3) | 0.16057 (15) | 0.0240 (5) | |
C14 | 0.2072 (4) | −0.0452 (4) | 0.16334 (17) | 0.0223 (6) | |
N14 | 0.2901 (3) | 0.0711 (3) | 0.22901 (14) | 0.0250 (6) | |
C15 | 0.1471 (4) | 0.0160 (4) | 0.09847 (17) | 0.0216 (6) | |
N15 | 0.1604 (3) | 0.1771 (3) | 0.09448 (15) | 0.0262 (6) | |
O15 | 0.2394 (3) | 0.2984 (2) | 0.15520 (13) | 0.0306 (5) | |
C16 | 0.0545 (4) | −0.1182 (4) | 0.03139 (17) | 0.0227 (6) | |
O16 | −0.0073 (3) | −0.0666 (3) | −0.02881 (12) | 0.0275 (5) | |
C167 | −0.0932 (4) | −0.1948 (4) | −0.10057 (18) | 0.0287 (7) | |
C161 | 0.0472 (4) | −0.2161 (4) | −0.15633 (18) | 0.0272 (7) | |
C162 | 0.1141 (5) | −0.3435 (4) | −0.1546 (2) | 0.0357 (8) | |
C163 | 0.2414 (5) | −0.3636 (5) | −0.2058 (2) | 0.0439 (9) | |
C164 | 0.3039 (5) | −0.2517 (5) | −0.2592 (2) | 0.0471 (9) | |
C165 | 0.2371 (5) | −0.1228 (4) | −0.2609 (2) | 0.0388 (8) | |
C166 | 0.1097 (5) | −0.1046 (4) | −0.21054 (19) | 0.0324 (7) | |
C17 | 0.3394 (4) | 0.0235 (4) | 0.30105 (18) | 0.0255 (6) | |
C177 | 0.4611 (4) | 0.1883 (4) | 0.35974 (18) | 0.0296 (7) | |
C171 | 0.6462 (4) | 0.2759 (4) | 0.33286 (17) | 0.0262 (7) | |
C172 | 0.7875 (5) | 0.2307 (4) | 0.3533 (2) | 0.0348 (7) | |
C173 | 0.9596 (5) | 0.3103 (5) | 0.3295 (2) | 0.0376 (8) | |
C174 | 0.9908 (5) | 0.4387 (4) | 0.2848 (2) | 0.0372 (8) | |
C175 | 0.8518 (5) | 0.4869 (4) | 0.26380 (19) | 0.0347 (8) | |
C176 | 0.6808 (4) | 0.4062 (4) | 0.28762 (19) | 0.0308 (7) | |
C18 | 0.1706 (4) | −0.0666 (4) | 0.34322 (18) | 0.0275 (7) | |
O181 | 0.0266 (3) | −0.0607 (3) | 0.33049 (14) | 0.0387 (6) | |
O182 | 0.2141 (3) | −0.1407 (3) | 0.39837 (13) | 0.0337 (5) | |
C19 | 0.0717 (4) | −0.2167 (4) | 0.4498 (2) | 0.0343 (7) | |
C110 | 0.1538 (5) | −0.2719 (6) | 0.5128 (3) | 0.0509 (10) | |
N21 | 0.4828 (3) | 0.2320 (3) | −0.04116 (15) | 0.0274 (6) | |
C22 | 0.3976 (4) | 0.2719 (4) | −0.10001 (18) | 0.0240 (6) | |
N22 | 0.2352 (3) | 0.2700 (3) | −0.08595 (16) | 0.0293 (6) | |
N23 | 0.4645 (3) | 0.3201 (3) | −0.16885 (15) | 0.0245 (5) | |
C24 | 0.6208 (4) | 0.3054 (4) | −0.18474 (18) | 0.0237 (6) | |
N24 | 0.6952 (3) | 0.3525 (3) | −0.25112 (15) | 0.0280 (6) | |
C25 | 0.7164 (4) | 0.2455 (4) | −0.13176 (19) | 0.0262 (7) | |
N25 | 0.8677 (4) | 0.2153 (4) | −0.14242 (17) | 0.0344 (6) | |
O25 | 0.9404 (3) | 0.2381 (3) | −0.20923 (15) | 0.0399 (6) | |
C26 | 0.6390 (4) | 0.2230 (4) | −0.05630 (18) | 0.0250 (6) | |
O26 | 0.7375 (3) | 0.1916 (3) | −0.00212 (13) | 0.0354 (5) | |
C267 | 0.6668 (5) | 0.1644 (4) | 0.07555 (19) | 0.0334 (8) | |
C261 | 0.6380 (4) | −0.0157 (4) | 0.0852 (2) | 0.0291 (7) | |
C262 | 0.5376 (5) | −0.1581 (5) | 0.0281 (2) | 0.0467 (10) | |
C263 | 0.5142 (6) | −0.3246 (5) | 0.0412 (4) | 0.0704 (17) | |
C264 | 0.5878 (7) | −0.3473 (6) | 0.1109 (4) | 0.0721 (16) | |
C265 | 0.6852 (6) | −0.2060 (6) | 0.1665 (3) | 0.0595 (12) | |
C266 | 0.7104 (5) | −0.0426 (5) | 0.1543 (2) | 0.0371 (8) | |
C27 | 0.6230 (4) | 0.4392 (4) | −0.30142 (18) | 0.0260 (7) | |
C277 | 0.7688 (4) | 0.5249 (4) | −0.3556 (2) | 0.0290 (7) | |
C271 | 0.7171 (4) | 0.6401 (4) | −0.40159 (19) | 0.0291 (7) | |
C272 | 0.6541 (5) | 0.5842 (5) | −0.4818 (2) | 0.0369 (8) | |
C273 | 0.6065 (5) | 0.6922 (6) | −0.5229 (2) | 0.0464 (9) | |
C274 | 0.6180 (5) | 0.8537 (6) | −0.4845 (3) | 0.0486 (10) | |
C275 | 0.6814 (5) | 0.9103 (5) | −0.4047 (2) | 0.0441 (9) | |
C276 | 0.7310 (4) | 0.8037 (4) | −0.3643 (2) | 0.0357 (8) | |
C28 | 0.4558 (4) | 0.3088 (4) | −0.3519 (2) | 0.0319 (7) | |
O281 | 0.4513 (4) | 0.1771 (3) | −0.39268 (19) | 0.0582 (8) | |
O282 | 0.3187 (3) | 0.3594 (4) | −0.34457 (15) | 0.0477 (7) | |
C29 | 0.1453 (5) | 0.2399 (7) | −0.3849 (3) | 0.0615 (12) | |
C210 | 0.1270 (7) | 0.2630 (6) | −0.4673 (3) | 0.0672 (13) | |
H12A | 0.1476 | −0.5155 | 0.1163 | 0.035* | |
H12B | 0.0202 | −0.5584 | 0.0415 | 0.035* | |
H14 | 0.3160 | 0.1818 | 0.2285 | 0.030* | |
H16A | −0.1777 | −0.1576 | −0.1285 | 0.034* | |
H16B | −0.1633 | −0.3076 | −0.0855 | 0.034* | |
H162 | 0.0725 | −0.4194 | −0.1175 | 0.043* | |
H163 | 0.2857 | −0.4535 | −0.2044 | 0.053* | |
H164 | 0.3919 | −0.2637 | −0.2944 | 0.057* | |
H165 | 0.2798 | −0.0458 | −0.2974 | 0.047* | |
H166 | 0.0639 | −0.0159 | −0.2126 | 0.039* | |
H17 | 0.4058 | −0.0563 | 0.2871 | 0.031* | |
H17A | 0.4000 | 0.2724 | 0.3676 | 0.035* | |
H17B | 0.4746 | 0.1567 | 0.4122 | 0.035* | |
H172 | 0.7669 | 0.1429 | 0.3844 | 0.042* | |
H173 | 1.0550 | 0.2765 | 0.3439 | 0.045* | |
H174 | 1.1081 | 0.4940 | 0.2685 | 0.045* | |
H175 | 0.8732 | 0.5753 | 0.2330 | 0.042* | |
H176 | 0.5856 | 0.4402 | 0.2729 | 0.037* | |
H19A | −0.0273 | −0.3175 | 0.4181 | 0.041* | |
H19B | 0.0216 | −0.1298 | 0.4741 | 0.041* | |
H11A | 0.2466 | −0.1700 | 0.5457 | 0.076* | |
H11B | 0.2087 | −0.3528 | 0.4879 | 0.076* | |
H11C | 0.0605 | −0.3296 | 0.5466 | 0.076* | |
H22A | 0.1615 | 0.2775 | −0.1231 | 0.035* | |
H22B | 0.1805 | 0.2268 | −0.0453 | 0.035* | |
H24 | 0.7914 | 0.3303 | −0.2649 | 0.034* | |
H26A | 0.5513 | 0.1825 | 0.0787 | 0.040* | |
H26B | 0.7533 | 0.2488 | 0.1191 | 0.040* | |
H262 | 0.4852 | −0.1437 | −0.0193 | 0.056* | |
H263 | 0.4471 | −0.4234 | 0.0019 | 0.085* | |
H264 | 0.5699 | −0.4606 | 0.1195 | 0.087* | |
H265 | 0.7364 | −0.2203 | 0.2142 | 0.071* | |
H266 | 0.7790 | 0.0548 | 0.1940 | 0.045* | |
H27 | 0.5906 | 0.5306 | −0.2668 | 0.031* | |
H27A | 0.8828 | 0.5948 | −0.3223 | 0.035* | |
H27B | 0.7906 | 0.4332 | −0.3940 | 0.035* | |
H272 | 0.6434 | 0.4719 | −0.5085 | 0.044* | |
H273 | 0.5657 | 0.6541 | −0.5781 | 0.056* | |
H274 | 0.5826 | 0.9259 | −0.5126 | 0.058* | |
H275 | 0.6908 | 1.0221 | −0.3778 | 0.053* | |
H276 | 0.7757 | 0.8439 | −0.3096 | 0.043* | |
H29A | 0.0467 | 0.2600 | −0.3552 | 0.074* | |
H29B | 0.1342 | 0.1190 | −0.3849 | 0.074* | |
H21A | 0.2190 | 0.2346 | −0.4978 | 0.101* | |
H21B | 0.1430 | 0.3839 | −0.4674 | 0.101* | |
H21C | 0.0068 | 0.1861 | −0.4918 | 0.101* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N11 | 0.0281 (13) | 0.0235 (13) | 0.0228 (13) | 0.0103 (11) | 0.0018 (10) | 0.0044 (10) |
C12 | 0.0249 (14) | 0.0270 (16) | 0.0223 (16) | 0.0115 (13) | 0.0065 (12) | 0.0081 (12) |
N12 | 0.0356 (14) | 0.0240 (13) | 0.0295 (14) | 0.0127 (12) | −0.0019 (11) | 0.0051 (11) |
N13 | 0.0267 (13) | 0.0198 (12) | 0.0242 (14) | 0.0062 (10) | 0.0038 (10) | 0.0060 (10) |
C14 | 0.0240 (14) | 0.0240 (15) | 0.0195 (15) | 0.0090 (12) | 0.0039 (11) | 0.0056 (11) |
N14 | 0.0338 (13) | 0.0174 (12) | 0.0214 (13) | 0.0063 (11) | −0.0011 (10) | 0.0050 (10) |
C15 | 0.0229 (14) | 0.0226 (14) | 0.0223 (15) | 0.0104 (12) | 0.0067 (12) | 0.0076 (11) |
N15 | 0.0311 (14) | 0.0234 (13) | 0.0228 (14) | 0.0087 (11) | 0.0041 (11) | 0.0038 (10) |
O15 | 0.0412 (13) | 0.0199 (10) | 0.0263 (12) | 0.0075 (10) | −0.0025 (9) | 0.0025 (9) |
C16 | 0.0231 (14) | 0.0278 (16) | 0.0197 (15) | 0.0125 (13) | 0.0038 (12) | 0.0041 (11) |
O16 | 0.0360 (12) | 0.0284 (11) | 0.0206 (11) | 0.0159 (10) | −0.0004 (9) | 0.0029 (8) |
C167 | 0.0329 (17) | 0.0324 (17) | 0.0220 (16) | 0.0149 (14) | −0.0035 (13) | 0.0026 (12) |
C161 | 0.0330 (16) | 0.0261 (15) | 0.0193 (16) | 0.0100 (13) | −0.0047 (12) | −0.0015 (12) |
C162 | 0.046 (2) | 0.0350 (18) | 0.0306 (18) | 0.0185 (16) | 0.0071 (15) | 0.0099 (14) |
C163 | 0.057 (2) | 0.044 (2) | 0.044 (2) | 0.0311 (18) | 0.0186 (18) | 0.0145 (16) |
C164 | 0.057 (2) | 0.051 (2) | 0.038 (2) | 0.025 (2) | 0.0194 (18) | 0.0103 (17) |
C165 | 0.051 (2) | 0.0291 (17) | 0.0302 (19) | 0.0075 (16) | 0.0073 (15) | 0.0072 (14) |
C166 | 0.0436 (19) | 0.0271 (16) | 0.0256 (17) | 0.0137 (15) | −0.0025 (14) | 0.0015 (13) |
C17 | 0.0305 (16) | 0.0258 (15) | 0.0199 (15) | 0.0081 (13) | 0.0006 (12) | 0.0088 (12) |
C177 | 0.0320 (16) | 0.0295 (16) | 0.0217 (16) | 0.0047 (14) | 0.0010 (13) | 0.0056 (13) |
C171 | 0.0303 (17) | 0.0233 (15) | 0.0200 (15) | 0.0059 (13) | 0.0001 (12) | 0.0010 (12) |
C172 | 0.0388 (18) | 0.0320 (17) | 0.0317 (18) | 0.0098 (15) | −0.0011 (14) | 0.0094 (13) |
C173 | 0.0337 (18) | 0.0383 (19) | 0.039 (2) | 0.0126 (16) | −0.0008 (15) | 0.0049 (15) |
C174 | 0.0331 (18) | 0.0371 (18) | 0.0331 (19) | 0.0063 (15) | 0.0091 (15) | −0.0003 (15) |
C175 | 0.0420 (19) | 0.0322 (17) | 0.0276 (18) | 0.0110 (16) | 0.0063 (14) | 0.0058 (14) |
C176 | 0.0346 (17) | 0.0303 (16) | 0.0275 (17) | 0.0136 (15) | 0.0007 (13) | 0.0021 (13) |
C18 | 0.0327 (17) | 0.0243 (15) | 0.0241 (17) | 0.0083 (13) | −0.0006 (13) | 0.0058 (12) |
O181 | 0.0346 (13) | 0.0420 (13) | 0.0416 (14) | 0.0134 (11) | 0.0014 (11) | 0.0157 (11) |
O182 | 0.0333 (12) | 0.0388 (12) | 0.0298 (12) | 0.0099 (10) | 0.0060 (9) | 0.0162 (10) |
C19 | 0.0329 (17) | 0.0371 (18) | 0.0303 (17) | 0.0074 (15) | 0.0095 (14) | 0.0121 (14) |
C110 | 0.045 (2) | 0.070 (3) | 0.047 (2) | 0.022 (2) | 0.0150 (18) | 0.034 (2) |
N21 | 0.0278 (13) | 0.0327 (14) | 0.0247 (14) | 0.0140 (12) | 0.0018 (11) | 0.0071 (11) |
C22 | 0.0240 (15) | 0.0214 (15) | 0.0269 (16) | 0.0091 (13) | 0.0014 (12) | 0.0041 (12) |
N22 | 0.0242 (13) | 0.0375 (15) | 0.0293 (15) | 0.0144 (12) | 0.0024 (11) | 0.0076 (12) |
N23 | 0.0237 (12) | 0.0276 (13) | 0.0242 (14) | 0.0110 (11) | 0.0028 (10) | 0.0070 (10) |
C24 | 0.0244 (15) | 0.0247 (15) | 0.0240 (16) | 0.0116 (13) | 0.0005 (12) | 0.0045 (12) |
N24 | 0.0272 (13) | 0.0384 (15) | 0.0276 (14) | 0.0201 (12) | 0.0069 (11) | 0.0130 (11) |
C25 | 0.0226 (14) | 0.0307 (16) | 0.0285 (17) | 0.0116 (13) | 0.0017 (12) | 0.0103 (13) |
N25 | 0.0309 (14) | 0.0433 (16) | 0.0373 (16) | 0.0178 (13) | 0.0109 (12) | 0.0197 (13) |
O25 | 0.0358 (13) | 0.0585 (16) | 0.0427 (14) | 0.0290 (12) | 0.0181 (11) | 0.0282 (12) |
C26 | 0.0231 (15) | 0.0272 (16) | 0.0274 (17) | 0.0109 (13) | −0.0004 (12) | 0.0085 (12) |
O26 | 0.0353 (13) | 0.0530 (15) | 0.0289 (13) | 0.0234 (11) | 0.0054 (10) | 0.0205 (11) |
C267 | 0.0422 (19) | 0.0419 (19) | 0.0191 (16) | 0.0185 (16) | −0.0008 (14) | 0.0073 (14) |
C261 | 0.0253 (15) | 0.0305 (17) | 0.0307 (18) | 0.0097 (13) | 0.0086 (13) | 0.0045 (13) |
C262 | 0.0363 (19) | 0.047 (2) | 0.042 (2) | 0.0055 (18) | 0.0061 (16) | −0.0058 (17) |
C263 | 0.054 (3) | 0.030 (2) | 0.099 (4) | −0.006 (2) | 0.038 (3) | −0.017 (2) |
C264 | 0.074 (3) | 0.041 (3) | 0.114 (5) | 0.027 (3) | 0.053 (3) | 0.034 (3) |
C265 | 0.068 (3) | 0.056 (3) | 0.075 (3) | 0.035 (2) | 0.031 (2) | 0.040 (3) |
C266 | 0.0398 (19) | 0.044 (2) | 0.036 (2) | 0.0227 (17) | 0.0060 (15) | 0.0149 (16) |
C27 | 0.0284 (15) | 0.0312 (16) | 0.0261 (16) | 0.0178 (14) | 0.0055 (12) | 0.0098 (13) |
C277 | 0.0248 (15) | 0.0330 (17) | 0.0307 (17) | 0.0107 (14) | 0.0049 (13) | 0.0100 (13) |
C271 | 0.0214 (15) | 0.0361 (18) | 0.0297 (17) | 0.0098 (14) | 0.0023 (12) | 0.0080 (13) |
C272 | 0.0378 (18) | 0.0392 (19) | 0.0317 (19) | 0.0111 (16) | 0.0030 (14) | 0.0089 (14) |
C273 | 0.045 (2) | 0.066 (3) | 0.035 (2) | 0.022 (2) | 0.0055 (16) | 0.0225 (19) |
C274 | 0.039 (2) | 0.063 (3) | 0.060 (3) | 0.0250 (19) | 0.0091 (18) | 0.039 (2) |
C275 | 0.0362 (19) | 0.036 (2) | 0.063 (3) | 0.0152 (17) | 0.0077 (18) | 0.0120 (18) |
C276 | 0.0322 (17) | 0.0335 (18) | 0.040 (2) | 0.0113 (15) | 0.0000 (14) | 0.0054 (14) |
C28 | 0.0324 (18) | 0.0337 (18) | 0.0367 (19) | 0.0160 (15) | 0.0036 (14) | 0.0170 (15) |
O281 | 0.0538 (16) | 0.0290 (14) | 0.088 (2) | 0.0187 (13) | −0.0222 (15) | −0.0056 (14) |
O282 | 0.0350 (13) | 0.0757 (18) | 0.0347 (14) | 0.0275 (13) | −0.0034 (11) | 0.0011 (12) |
C29 | 0.0309 (19) | 0.102 (4) | 0.047 (2) | 0.018 (2) | −0.0045 (17) | 0.016 (2) |
C210 | 0.075 (3) | 0.060 (3) | 0.060 (3) | 0.015 (2) | −0.021 (2) | 0.019 (2) |
Geometric parameters (Å, º) top
N11—C16 | 1.303 (4) | N21—C26 | 1.303 (4) |
N11—C12 | 1.371 (4) | N21—C22 | 1.359 (4) |
C12—N12 | 1.327 (4) | C22—N22 | 1.317 (4) |
C12—N13 | 1.344 (4) | C22—N23 | 1.356 (4) |
N12—H12A | 0.8784 | N22—H22A | 0.8853 |
N12—H12B | 0.8842 | N22—H22B | 0.8806 |
N13—C14 | 1.331 (4) | N23—C24 | 1.325 (4) |
C14—N14 | 1.334 (4) | C24—N24 | 1.334 (4) |
C14—C15 | 1.442 (4) | C24—C25 | 1.441 (4) |
N14—C17 | 1.446 (4) | N24—C27 | 1.453 (4) |
N14—H14 | 0.8800 | N24—H24 | 0.8800 |
C15—N15 | 1.336 (4) | C25—N25 | 1.332 (4) |
C15—C16 | 1.433 (4) | C25—C26 | 1.442 (4) |
N15—O15 | 1.289 (3) | N25—O25 | 1.292 (3) |
C16—O16 | 1.335 (4) | C26—O26 | 1.327 (4) |
O16—C167 | 1.454 (4) | O26—C267 | 1.463 (4) |
C167—C161 | 1.516 (5) | C267—C261 | 1.488 (5) |
C167—H16A | 0.9900 | C267—H26A | 0.9900 |
C167—H16B | 0.9900 | C267—H26B | 0.9900 |
C161—C162 | 1.367 (5) | C261—C262 | 1.380 (5) |
C161—C166 | 1.395 (5) | C261—C266 | 1.394 (5) |
C162—C163 | 1.384 (5) | C262—C263 | 1.405 (7) |
C162—H162 | 0.9500 | C262—H262 | 0.9500 |
C163—C164 | 1.387 (5) | C263—C264 | 1.390 (8) |
C163—H163 | 0.9500 | C263—H263 | 0.9500 |
C164—C165 | 1.378 (5) | C264—C265 | 1.355 (8) |
C164—H164 | 0.9500 | C264—H264 | 0.9500 |
C165—C166 | 1.371 (5) | C265—C266 | 1.369 (5) |
C165—H165 | 0.9500 | C265—H265 | 0.9500 |
C166—H166 | 0.9500 | C266—H266 | 0.9500 |
C17—C18 | 1.538 (4) | C27—C28 | 1.519 (4) |
C17—C177 | 1.544 (4) | C27—C277 | 1.537 (4) |
C17—H17 | 1.0000 | C27—H27 | 1.0000 |
C177—C171 | 1.507 (4) | C277—C271 | 1.507 (4) |
C177—H17A | 0.9900 | C277—H27A | 0.9900 |
C177—H17B | 0.9900 | C277—H27B | 0.9900 |
C171—C172 | 1.376 (5) | C271—C276 | 1.379 (5) |
C171—C176 | 1.395 (4) | C271—C272 | 1.388 (5) |
C172—C173 | 1.391 (5) | C272—C273 | 1.390 (5) |
C172—H172 | 0.9500 | C272—H272 | 0.9500 |
C173—C174 | 1.377 (5) | C273—C274 | 1.374 (6) |
C173—H173 | 0.9500 | C273—H273 | 0.9500 |
C174—C175 | 1.378 (5) | C274—C275 | 1.383 (6) |
C174—H174 | 0.9500 | C274—H274 | 0.9500 |
C175—C176 | 1.385 (5) | C275—C276 | 1.380 (5) |
C175—H175 | 0.9500 | C275—H275 | 0.9500 |
C176—H176 | 0.9500 | C276—H276 | 0.9500 |
C18—O181 | 1.189 (4) | C28—O281 | 1.191 (4) |
C18—O182 | 1.321 (4) | C28—O282 | 1.313 (4) |
O182—C19 | 1.466 (4) | O282—C29 | 1.458 (5) |
C19—C110 | 1.474 (5) | C29—C210 | 1.460 (6) |
C19—H19A | 0.9900 | C29—H29A | 0.9900 |
C19—H19B | 0.9900 | C29—H29B | 0.9900 |
C110—H11A | 0.9800 | C210—H21A | 0.9800 |
C110—H11B | 0.9800 | C210—H21B | 0.9800 |
C110—H11C | 0.9800 | C210—H21C | 0.9800 |
| | | |
C16—N11—C12 | 115.7 (2) | C26—N21—C22 | 116.0 (2) |
N12—C12—N13 | 117.6 (3) | N22—C22—N23 | 117.4 (3) |
N12—C12—N11 | 114.7 (3) | N22—C22—N21 | 115.4 (3) |
N13—C12—N11 | 127.7 (3) | N23—C22—N21 | 127.2 (3) |
C12—N12—H12A | 120.7 | C22—N22—H22A | 122.6 |
C12—N12—H12B | 118.1 | C22—N22—H22B | 120.5 |
H12A—N12—H12B | 119.9 | H22A—N22—H22B | 113.9 |
C14—N13—C12 | 115.5 (2) | C24—N23—C22 | 115.8 (2) |
N13—C14—N14 | 119.1 (3) | N23—C24—N24 | 118.9 (3) |
N13—C14—C15 | 123.1 (2) | N23—C24—C25 | 122.5 (3) |
N14—C14—C15 | 117.8 (2) | N24—C24—C25 | 118.6 (3) |
C14—N14—C17 | 123.0 (2) | C24—N24—C27 | 122.3 (2) |
C14—N14—H14 | 118.5 | C24—N24—H24 | 118.8 |
C17—N14—H14 | 118.5 | C27—N24—H24 | 118.8 |
N15—C15—C16 | 117.1 (3) | N25—C25—C24 | 128.6 (3) |
N15—C15—C14 | 128.8 (2) | N25—C25—C26 | 117.0 (3) |
C16—C15—C14 | 114.1 (2) | C24—C25—C26 | 114.3 (2) |
O15—N15—C15 | 117.8 (2) | O25—N25—C25 | 117.7 (3) |
N11—C16—O16 | 120.5 (3) | N21—C26—O26 | 121.3 (3) |
N11—C16—C15 | 123.9 (3) | N21—C26—C25 | 123.1 (3) |
O16—C16—C15 | 115.6 (2) | O26—C26—C25 | 115.5 (2) |
C16—O16—C167 | 118.3 (2) | C26—O26—C267 | 118.8 (2) |
O16—C167—C161 | 110.5 (2) | O26—C267—C261 | 109.2 (3) |
O16—C167—H16A | 109.5 | O26—C267—H26A | 109.8 |
C161—C167—H16A | 109.5 | C261—C267—H26A | 109.8 |
O16—C167—H16B | 109.5 | O26—C267—H26B | 109.8 |
C161—C167—H16B | 109.5 | C261—C267—H26B | 109.8 |
H16A—C167—H16B | 108.1 | H26A—C267—H26B | 108.3 |
C162—C161—C166 | 119.1 (3) | C262—C261—C266 | 118.8 (3) |
C162—C161—C167 | 121.1 (3) | C262—C261—C267 | 121.7 (3) |
C166—C161—C167 | 119.8 (3) | C266—C261—C267 | 119.5 (3) |
C161—C162—C163 | 121.1 (3) | C261—C262—C263 | 118.8 (4) |
C161—C162—H162 | 119.5 | C261—C262—H262 | 120.6 |
C163—C162—H162 | 119.5 | C263—C262—H262 | 120.6 |
C162—C163—C164 | 119.6 (3) | C264—C263—C262 | 121.1 (4) |
C162—C163—H163 | 120.2 | C264—C263—H263 | 119.5 |
C164—C163—H163 | 120.2 | C262—C263—H263 | 119.5 |
C165—C164—C163 | 119.4 (3) | C265—C264—C263 | 119.3 (4) |
C165—C164—H164 | 120.3 | C265—C264—H264 | 120.3 |
C163—C164—H164 | 120.3 | C263—C264—H264 | 120.3 |
C166—C165—C164 | 120.7 (3) | C264—C265—C266 | 120.4 (5) |
C166—C165—H165 | 119.6 | C264—C265—H265 | 119.8 |
C164—C165—H165 | 119.6 | C266—C265—H265 | 119.8 |
C165—C166—C161 | 120.1 (3) | C265—C266—C261 | 121.7 (4) |
C165—C166—H166 | 120.0 | C265—C266—H266 | 119.2 |
C161—C166—H166 | 120.0 | C261—C266—H266 | 119.2 |
N14—C17—C18 | 110.7 (2) | N24—C27—C28 | 110.0 (2) |
N14—C17—C177 | 109.7 (2) | N24—C27—C277 | 108.6 (2) |
C18—C17—C177 | 107.9 (2) | C28—C27—C277 | 110.2 (3) |
N14—C17—H17 | 109.5 | N24—C27—H27 | 109.3 |
C18—C17—H17 | 109.5 | C28—C27—H27 | 109.3 |
C177—C17—H17 | 109.5 | C277—C27—H27 | 109.3 |
C171—C177—C17 | 114.5 (2) | C271—C277—C27 | 112.6 (2) |
C171—C177—H17A | 108.6 | C271—C277—H27A | 109.1 |
C17—C177—H17A | 108.6 | C27—C277—H27A | 109.1 |
C171—C177—H17B | 108.6 | C271—C277—H27B | 109.1 |
C17—C177—H17B | 108.6 | C27—C277—H27B | 109.1 |
H17A—C177—H17B | 107.6 | H27A—C277—H27B | 107.8 |
C172—C171—C176 | 117.9 (3) | C276—C271—C272 | 118.6 (3) |
C172—C171—C177 | 120.6 (3) | C276—C271—C277 | 120.3 (3) |
C176—C171—C177 | 121.5 (3) | C272—C271—C277 | 121.0 (3) |
C171—C172—C173 | 121.6 (3) | C271—C272—C273 | 120.1 (4) |
C171—C172—H172 | 119.2 | C271—C272—H272 | 119.9 |
C173—C172—H172 | 119.2 | C273—C272—H272 | 119.9 |
C174—C173—C172 | 119.6 (3) | C274—C273—C272 | 120.5 (4) |
C174—C173—H173 | 120.2 | C274—C273—H273 | 119.7 |
C172—C173—H173 | 120.2 | C272—C273—H273 | 119.7 |
C173—C174—C175 | 120.0 (3) | C273—C274—C275 | 119.5 (3) |
C173—C174—H174 | 120.0 | C273—C274—H274 | 120.2 |
C175—C174—H174 | 120.0 | C275—C274—H274 | 120.2 |
C174—C175—C176 | 120.0 (3) | C276—C275—C274 | 119.8 (4) |
C174—C175—H175 | 120.0 | C276—C275—H275 | 120.1 |
C176—C175—H175 | 120.0 | C274—C275—H275 | 120.1 |
C175—C176—C171 | 121.0 (3) | C271—C276—C275 | 121.3 (3) |
C175—C176—H176 | 119.5 | C271—C276—H276 | 119.3 |
C171—C176—H176 | 119.5 | C275—C276—H276 | 119.3 |
O181—C18—O182 | 126.0 (3) | O281—C28—O282 | 124.8 (3) |
O181—C18—C17 | 124.4 (3) | O281—C28—C27 | 123.6 (3) |
O182—C18—C17 | 109.4 (3) | O282—C28—C27 | 111.6 (3) |
C18—O182—C19 | 116.1 (2) | C28—O282—C29 | 117.4 (3) |
O182—C19—C110 | 107.3 (3) | O282—C29—C210 | 111.2 (4) |
O182—C19—H19A | 110.3 | O282—C29—H29A | 109.4 |
C110—C19—H19A | 110.3 | C210—C29—H29A | 109.4 |
O182—C19—H19B | 110.3 | O282—C29—H29B | 109.4 |
C110—C19—H19B | 110.3 | C210—C29—H29B | 109.4 |
H19A—C19—H19B | 108.5 | H29A—C29—H29B | 108.0 |
C19—C110—H11A | 109.5 | C29—C210—H21A | 109.5 |
C19—C110—H11B | 109.5 | C29—C210—H21B | 109.5 |
H11A—C110—H11B | 109.5 | H21A—C210—H21B | 109.5 |
C19—C110—H11C | 109.5 | C29—C210—H21C | 109.5 |
H11A—C110—H11C | 109.5 | H21A—C210—H21C | 109.5 |
H11B—C110—H11C | 109.5 | H21B—C210—H21C | 109.5 |
| | | |
C16—N11—C12—N12 | −176.5 (3) | C26—N21—C22—N22 | 176.0 (3) |
C16—N11—C12—N13 | 4.4 (4) | C26—N21—C22—N23 | −7.2 (4) |
N12—C12—N13—C14 | 176.4 (3) | N22—C22—N23—C24 | −174.1 (3) |
N11—C12—N13—C14 | −4.5 (4) | N21—C22—N23—C24 | 9.1 (4) |
C12—N13—C14—N14 | −179.1 (3) | C22—N23—C24—N24 | −179.2 (3) |
C12—N13—C14—C15 | 1.3 (4) | C22—N23—C24—C25 | −1.2 (4) |
N13—C14—N14—C17 | −6.3 (4) | N23—C24—N24—C27 | 7.8 (4) |
C15—C14—N14—C17 | 173.3 (2) | C25—C24—N24—C27 | −170.3 (3) |
N13—C14—C15—N15 | 178.6 (3) | N23—C24—C25—N25 | 175.7 (3) |
N14—C14—C15—N15 | −0.9 (4) | N24—C24—C25—N25 | −6.2 (5) |
N13—C14—C15—C16 | 1.4 (4) | N23—C24—C25—C26 | −7.0 (4) |
N14—C14—C15—C16 | −178.1 (2) | N24—C24—C25—C26 | 171.0 (3) |
C16—C15—N15—O15 | 178.3 (2) | C24—C25—N25—O25 | −1.6 (5) |
C14—C15—N15—O15 | 1.2 (4) | C26—C25—N25—O25 | −178.8 (3) |
C12—N11—C16—O16 | 179.2 (3) | C22—N21—C26—O26 | 177.4 (3) |
C12—N11—C16—C15 | −1.0 (4) | C22—N21—C26—C25 | −2.8 (4) |
N15—C15—C16—N11 | −179.1 (3) | N25—C25—C26—N21 | −173.2 (3) |
C14—C15—C16—N11 | −1.6 (4) | C24—C25—C26—N21 | 9.2 (4) |
N15—C15—C16—O16 | 0.7 (4) | N25—C25—C26—O26 | 6.6 (4) |
C14—C15—C16—O16 | 178.2 (2) | C24—C25—C26—O26 | −170.9 (3) |
N11—C16—O16—C167 | −3.7 (4) | N21—C26—O26—C267 | 0.9 (4) |
C15—C16—O16—C167 | 176.5 (2) | C25—C26—O26—C267 | −179.0 (3) |
C16—O16—C167—C161 | −84.4 (3) | C26—O26—C267—C261 | 116.3 (3) |
O16—C167—C161—C162 | 94.5 (3) | O26—C267—C261—C262 | −52.9 (4) |
O16—C167—C161—C166 | −85.6 (3) | O26—C267—C261—C266 | 128.6 (3) |
C166—C161—C162—C163 | −0.4 (5) | C266—C261—C262—C263 | −0.9 (5) |
C167—C161—C162—C163 | 179.6 (3) | C267—C261—C262—C263 | −179.4 (3) |
C161—C162—C163—C164 | 0.8 (6) | C261—C262—C263—C264 | 1.1 (6) |
C162—C163—C164—C165 | −0.5 (6) | C262—C263—C264—C265 | −0.8 (7) |
C163—C164—C165—C166 | −0.1 (6) | C263—C264—C265—C266 | 0.3 (6) |
C164—C165—C166—C161 | 0.5 (5) | C264—C265—C266—C261 | −0.1 (6) |
C162—C161—C166—C165 | −0.3 (5) | C262—C261—C266—C265 | 0.4 (5) |
C167—C161—C166—C165 | 179.7 (3) | C267—C261—C266—C265 | 179.0 (3) |
C14—N14—C17—C18 | −70.8 (4) | C24—N24—C27—C28 | −76.9 (4) |
C14—N14—C17—C177 | 170.2 (3) | C24—N24—C27—C277 | 162.4 (3) |
N14—C17—C177—C171 | −68.9 (3) | N24—C27—C277—C271 | −171.6 (3) |
C18—C17—C177—C171 | 170.4 (3) | C28—C27—C277—C271 | 67.8 (3) |
C17—C177—C171—C172 | −89.9 (3) | C27—C277—C271—C276 | 77.8 (4) |
C17—C177—C171—C176 | 90.9 (4) | C27—C277—C271—C272 | −101.8 (3) |
C176—C171—C172—C173 | −0.5 (5) | C276—C271—C272—C273 | 0.1 (5) |
C177—C171—C172—C173 | −179.7 (3) | C277—C271—C272—C273 | 179.8 (3) |
C171—C172—C173—C174 | 0.5 (5) | C271—C272—C273—C274 | −1.3 (5) |
C172—C173—C174—C175 | −0.3 (5) | C272—C273—C274—C275 | 1.5 (6) |
C173—C174—C175—C176 | 0.0 (5) | C273—C274—C275—C276 | −0.6 (5) |
C174—C175—C176—C171 | 0.0 (5) | C272—C271—C276—C275 | 0.9 (5) |
C172—C171—C176—C175 | 0.3 (4) | C277—C271—C276—C275 | −178.8 (3) |
C177—C171—C176—C175 | 179.5 (3) | C274—C275—C276—C271 | −0.6 (5) |
N14—C17—C18—O181 | −17.0 (4) | N24—C27—C28—O281 | −52.2 (4) |
C177—C17—C18—O181 | 103.0 (3) | C277—C27—C28—O281 | 67.5 (4) |
N14—C17—C18—O182 | 166.9 (2) | N24—C27—C28—O282 | 127.6 (3) |
C177—C17—C18—O182 | −73.1 (3) | C277—C27—C28—O282 | −112.6 (3) |
O181—C18—O182—C19 | −2.3 (4) | O281—C28—O282—C29 | 4.6 (5) |
C17—C18—O182—C19 | 173.8 (2) | C27—C28—O282—C29 | −175.3 (3) |
C18—O182—C19—C110 | −173.0 (3) | C28—O282—C29—C210 | −87.6 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N14—H14···O15 | 0.88 | 1.93 | 2.606 (3) | 132 |
N24—H24···O25 | 0.88 | 1.96 | 2.621 (4) | 131 |
N22—H22B···N15 | 0.88 | 2.48 | 3.302 (4) | 155 |
N22—H22B···O16 | 0.88 | 2.44 | 3.115 (3) | 133 |
N22—H22A···N25i | 0.88 | 2.22 | 2.925 (4) | 137 |
N22—H22A···O25i | 0.88 | 2.17 | 3.043 (4) | 167 |
N12—H12A···O15ii | 0.88 | 2.15 | 2.962 (4) | 153 |
N12—H12B···O26iii | 0.88 | 2.46 | 3.199 (4) | 142 |
Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z; (iii) x−1, y−1, z. |
(7) Ethyl
N-(2-benzylamino-6-benzyloxy-5-nitrosopyrimidin-4-yl)-
β-alaninate
top
Crystal data top
C23H25N5O4 | Z = 4 |
Mr = 435.48 | F(000) = 920 |
Triclinic, P1 | Dx = 1.342 Mg m−3 |
a = 8.6595 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 16.3567 (4) Å | Cell parameters from 9402 reflections |
c = 16.9014 (4) Å | θ = 1.3–27.5° |
α = 105.2210 (13)° | µ = 0.09 mm−1 |
β = 104.6960 (13)° | T = 150 K |
γ = 100.3720 (12)° | Plate, pink |
V = 2154.95 (9) Å3 | 0.40 × 0.40 × 0.05 mm |
Data collection top
Kappa-CCD diffractometer | 9402 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 5874 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.092 |
φ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 1.3° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −11→11 |
Tmin = 0.963, Tmax = 0.995 | k = −21→21 |
33749 measured reflections | l = −20→21 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.186 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.1133P)2] where P = (Fo2 + 2Fc2)/3 |
9402 reflections | (Δ/σ)max < 0.001 |
579 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.51 e Å−3 |
Special details top
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm
[Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which
effectively corrects for absorption effects. High redundancy data were used in
the scaling program hence the 'multi-scan' code word was used. No transmission
coefficients are available from the program (only scale factors for each
frame). The scale factors in the experimental table are calculated from the
'size' command in the SHELXL97 input file. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N11 | 1.0249 (2) | 0.60550 (11) | 0.36876 (11) | 0.0258 (4) | |
C12 | 1.0964 (3) | 0.53673 (14) | 0.35369 (14) | 0.0237 (5) | |
C110 | 0.9030 (3) | 0.05529 (15) | 0.06382 (17) | 0.0368 (6) | |
C111 | 0.7752 (3) | −0.00845 (16) | 0.07868 (18) | 0.0444 (7) | |
C121 | 1.1768 (3) | 0.36350 (15) | 0.38856 (14) | 0.0260 (5) | |
C122 | 1.2141 (3) | 0.29965 (16) | 0.32948 (15) | 0.0326 (6) | |
C123 | 1.1232 (3) | 0.21208 (16) | 0.30233 (16) | 0.0392 (6) | |
C124 | 0.9959 (3) | 0.18862 (16) | 0.33340 (16) | 0.0388 (6) | |
C125 | 0.9584 (3) | 0.25153 (17) | 0.39191 (17) | 0.0387 (6) | |
C126 | 1.0498 (3) | 0.33901 (16) | 0.41971 (15) | 0.0321 (6) | |
C127 | 1.2779 (3) | 0.45847 (14) | 0.42033 (14) | 0.0275 (5) | |
N12 | 1.1799 (2) | 0.52204 (12) | 0.42361 (11) | 0.0262 (4) | |
N13 | 1.0906 (2) | 0.48350 (12) | 0.27675 (11) | 0.0246 (4) | |
N14 | 0.9987 (2) | 0.44785 (12) | 0.12929 (12) | 0.0270 (4) | |
C14 | 1.0081 (3) | 0.49941 (14) | 0.20697 (14) | 0.0237 (5) | |
C15 | 0.9297 (3) | 0.57093 (14) | 0.21315 (14) | 0.0243 (5) | |
N15 | 0.8397 (2) | 0.59235 (12) | 0.14840 (12) | 0.0315 (5) | |
O15 | 0.8223 (2) | 0.54515 (11) | 0.07058 (10) | 0.0364 (4) | |
C16 | 0.9478 (3) | 0.62152 (14) | 0.30028 (14) | 0.0254 (5) | |
C161 | 0.8292 (3) | 0.82000 (15) | 0.38664 (15) | 0.0300 (5) | |
C162 | 0.8311 (4) | 0.87995 (19) | 0.46225 (18) | 0.0534 (8) | |
C163 | 0.7762 (4) | 0.9539 (2) | 0.4606 (2) | 0.0643 (10) | |
C164 | 0.7198 (4) | 0.96951 (17) | 0.38387 (18) | 0.0444 (7) | |
C165 | 0.7148 (3) | 0.91037 (16) | 0.30858 (17) | 0.0381 (6) | |
C166 | 0.7697 (3) | 0.83533 (16) | 0.30975 (16) | 0.0344 (6) | |
C167 | 0.8931 (3) | 0.74143 (15) | 0.39275 (15) | 0.0308 (5) | |
O16 | 0.8797 (2) | 0.68909 (10) | 0.30716 (10) | 0.0305 (4) | |
C17 | 1.0632 (3) | 0.37082 (14) | 0.11721 (15) | 0.0273 (5) | |
C18 | 0.9430 (3) | 0.29325 (14) | 0.12118 (14) | 0.0260 (5) | |
C19 | 0.9878 (3) | 0.20869 (15) | 0.09095 (14) | 0.0278 (5) | |
O191 | 1.1054 (2) | 0.20011 (11) | 0.06813 (12) | 0.0414 (5) | |
O192 | 0.8746 (2) | 0.14106 (10) | 0.09233 (10) | 0.0328 (4) | |
N21 | 0.5303 (2) | 0.52903 (11) | −0.15940 (11) | 0.0249 (4) | |
C22 | 0.5347 (3) | 0.60947 (14) | −0.10538 (14) | 0.0236 (5) | |
C210 | 0.7199 (3) | 0.99200 (19) | −0.29453 (19) | 0.0487 (7) | |
C211 | 0.8936 (3) | 1.0462 (2) | −0.2688 (2) | 0.0531 (8) | |
C221 | 0.4696 (3) | 0.72026 (14) | 0.06291 (13) | 0.0269 (5) | |
C222 | 0.4357 (3) | 0.80224 (15) | 0.07891 (15) | 0.0320 (6) | |
C223 | 0.2947 (3) | 0.81434 (17) | 0.09916 (16) | 0.0387 (6) | |
C224 | 0.1824 (3) | 0.74482 (18) | 0.10318 (15) | 0.0386 (6) | |
C225 | 0.2154 (3) | 0.66285 (17) | 0.08679 (15) | 0.0369 (6) | |
C226 | 0.3562 (3) | 0.65088 (15) | 0.06777 (14) | 0.0317 (6) | |
C227 | 0.6261 (3) | 0.70802 (14) | 0.04390 (14) | 0.0282 (5) | |
N22 | 0.6036 (2) | 0.62425 (12) | −0.02172 (12) | 0.0286 (4) | |
N23 | 0.4804 (2) | 0.67442 (11) | −0.12799 (11) | 0.0245 (4) | |
C24 | 0.4181 (3) | 0.66066 (14) | −0.21238 (14) | 0.0232 (5) | |
N24 | 0.3715 (2) | 0.72597 (11) | −0.23708 (12) | 0.0261 (4) | |
C25 | 0.4026 (3) | 0.57868 (14) | −0.27663 (13) | 0.0235 (5) | |
N25 | 0.3449 (2) | 0.55658 (12) | −0.36322 (12) | 0.0297 (5) | |
O25 | 0.2950 (2) | 0.61498 (11) | −0.39373 (10) | 0.0352 (4) | |
C26 | 0.4659 (3) | 0.51608 (14) | −0.24142 (14) | 0.0241 (5) | |
C261 | 0.5591 (3) | 0.31559 (14) | −0.34602 (14) | 0.0257 (5) | |
C262 | 0.6313 (3) | 0.24916 (15) | −0.33096 (15) | 0.0341 (6) | |
C263 | 0.6552 (3) | 0.18896 (17) | −0.39780 (17) | 0.0402 (6) | |
C264 | 0.6095 (3) | 0.19365 (17) | −0.48069 (16) | 0.0385 (6) | |
C265 | 0.5379 (3) | 0.25925 (16) | −0.49580 (15) | 0.0346 (6) | |
C266 | 0.5124 (3) | 0.31946 (15) | −0.42890 (15) | 0.0306 (5) | |
C267 | 0.5375 (3) | 0.37955 (14) | −0.26986 (15) | 0.0291 (5) | |
O26 | 0.46020 (19) | 0.44173 (9) | −0.30050 (9) | 0.0292 (4) | |
C27 | 0.3916 (3) | 0.81161 (14) | −0.17607 (14) | 0.0263 (5) | |
C28 | 0.5539 (3) | 0.87639 (15) | −0.16100 (14) | 0.0302 (5) | |
C29 | 0.5584 (3) | 0.90424 (14) | −0.23811 (15) | 0.0296 (5) | |
O291 | 0.4459 (2) | 0.88055 (12) | −0.30486 (11) | 0.0455 (5) | |
O292 | 0.7037 (2) | 0.96039 (11) | −0.22346 (11) | 0.0360 (4) | |
H11A | 1.0154 | 0.0558 | 0.0970 | 0.044* | |
H11B | 0.8932 | 0.0385 | 0.0017 | 0.044* | |
H11C | 0.7896 | 0.0072 | 0.1407 | 0.067* | |
H11D | 0.7876 | −0.0679 | 0.0574 | 0.067* | |
H11E | 0.6645 | −0.0064 | 0.0477 | 0.067* | |
H122 | 1.3016 | 0.3156 | 0.3075 | 0.039* | |
H123 | 1.1495 | 0.1685 | 0.2622 | 0.047* | |
H124 | 0.9339 | 0.1290 | 0.3145 | 0.047* | |
H125 | 0.8703 | 0.2354 | 0.4134 | 0.046* | |
H126 | 1.0241 | 0.3821 | 0.4606 | 0.038* | |
H12A | 1.3556 | 0.4713 | 0.4790 | 0.033* | |
H12B | 1.3447 | 0.4660 | 0.3819 | 0.033* | |
H12 | 1.1758 | 0.5520 | 0.4742 | 0.031* | |
H14 | 0.9515 | 0.4610 | 0.0834 | 0.032* | |
H162 | 0.8706 | 0.8701 | 0.5158 | 0.064* | |
H163 | 0.7775 | 0.9942 | 0.5129 | 0.077* | |
H164 | 0.6844 | 1.0211 | 0.3831 | 0.053* | |
H165 | 0.6737 | 0.9203 | 0.2552 | 0.046* | |
H166 | 0.7660 | 0.7946 | 0.2571 | 0.041* | |
H16A | 1.0101 | 0.7608 | 0.4301 | 0.037* | |
H16B | 0.8274 | 0.7063 | 0.4184 | 0.037* | |
H17A | 1.1705 | 0.3842 | 0.1628 | 0.033* | |
H17B | 1.0824 | 0.3556 | 0.0605 | 0.033* | |
H18A | 0.9419 | 0.3039 | 0.1814 | 0.031* | |
H18B | 0.8301 | 0.2881 | 0.0847 | 0.031* | |
H21A | 0.6413 | 1.0279 | −0.3059 | 0.058* | |
H21B | 0.6954 | 0.9419 | −0.3477 | 0.058* | |
H21C | 0.9166 | 1.0953 | −0.2158 | 0.080* | |
H21D | 0.9084 | 1.0691 | −0.3152 | 0.080* | |
H21E | 0.9700 | 1.0098 | −0.2585 | 0.080* | |
H222 | 0.5108 | 0.8505 | 0.0758 | 0.038* | |
H223 | 0.2746 | 0.8708 | 0.1104 | 0.046* | |
H224 | 0.0851 | 0.7529 | 0.1168 | 0.046* | |
H225 | 0.1392 | 0.6144 | 0.0888 | 0.044* | |
H226 | 0.3769 | 0.5945 | 0.0577 | 0.038* | |
H22A | 0.6702 | 0.7565 | 0.0242 | 0.034* | |
H22B | 0.7096 | 0.7120 | 0.0980 | 0.034* | |
H22 | 0.6372 | 0.5821 | −0.0049 | 0.034* | |
H24 | 0.3266 | 0.7168 | −0.2926 | 0.031* | |
H262 | 0.6642 | 0.2454 | −0.2742 | 0.041* | |
H263 | 0.7036 | 0.1437 | −0.3868 | 0.048* | |
H264 | 0.6271 | 0.1523 | −0.5265 | 0.046* | |
H265 | 0.5058 | 0.2631 | −0.5525 | 0.042* | |
H266 | 0.4620 | 0.3640 | −0.4403 | 0.037* | |
H26A | 0.4670 | 0.3478 | −0.2437 | 0.035* | |
H26B | 0.6464 | 0.4107 | −0.2254 | 0.035* | |
H27A | 0.3868 | 0.8046 | −0.1203 | 0.032* | |
H27B | 0.2987 | 0.8356 | −0.1983 | 0.032* | |
H28A | 0.5714 | 0.9290 | −0.1112 | 0.036* | |
H28B | 0.6458 | 0.8491 | −0.1461 | 0.036* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N11 | 0.0282 (10) | 0.0186 (10) | 0.0270 (10) | 0.0062 (8) | 0.0048 (8) | 0.0054 (8) |
C12 | 0.0226 (11) | 0.0205 (11) | 0.0246 (12) | 0.0014 (9) | 0.0044 (9) | 0.0078 (9) |
C110 | 0.0443 (15) | 0.0201 (13) | 0.0434 (15) | 0.0132 (11) | 0.0139 (12) | 0.0031 (11) |
C111 | 0.0517 (17) | 0.0235 (13) | 0.0504 (17) | 0.0066 (12) | 0.0104 (14) | 0.0077 (12) |
C121 | 0.0265 (12) | 0.0255 (12) | 0.0227 (12) | 0.0088 (10) | 0.0000 (9) | 0.0085 (9) |
C122 | 0.0350 (14) | 0.0304 (13) | 0.0316 (13) | 0.0121 (11) | 0.0098 (11) | 0.0072 (11) |
C123 | 0.0499 (16) | 0.0274 (13) | 0.0313 (14) | 0.0153 (12) | 0.0018 (12) | 0.0024 (11) |
C124 | 0.0383 (15) | 0.0259 (13) | 0.0411 (15) | 0.0031 (11) | −0.0037 (12) | 0.0123 (12) |
C125 | 0.0342 (14) | 0.0385 (15) | 0.0420 (15) | 0.0049 (12) | 0.0073 (12) | 0.0183 (13) |
C126 | 0.0342 (13) | 0.0323 (13) | 0.0287 (13) | 0.0103 (11) | 0.0073 (11) | 0.0098 (11) |
C127 | 0.0270 (12) | 0.0249 (12) | 0.0251 (12) | 0.0069 (10) | 0.0016 (10) | 0.0056 (10) |
N12 | 0.0320 (10) | 0.0242 (10) | 0.0200 (10) | 0.0101 (9) | 0.0048 (8) | 0.0048 (8) |
N13 | 0.0270 (10) | 0.0197 (9) | 0.0217 (10) | 0.0041 (8) | 0.0023 (8) | 0.0046 (8) |
N14 | 0.0330 (11) | 0.0208 (10) | 0.0211 (10) | 0.0052 (8) | 0.0015 (8) | 0.0053 (8) |
C14 | 0.0231 (11) | 0.0192 (11) | 0.0236 (12) | 0.0010 (9) | 0.0030 (9) | 0.0058 (9) |
C15 | 0.0254 (11) | 0.0173 (11) | 0.0259 (12) | 0.0028 (9) | 0.0039 (10) | 0.0060 (9) |
N15 | 0.0362 (11) | 0.0233 (10) | 0.0287 (11) | 0.0051 (9) | 0.0022 (9) | 0.0077 (9) |
O15 | 0.0478 (11) | 0.0284 (9) | 0.0269 (9) | 0.0113 (8) | 0.0021 (8) | 0.0075 (7) |
C16 | 0.0231 (11) | 0.0170 (11) | 0.0311 (13) | 0.0024 (9) | 0.0042 (10) | 0.0059 (9) |
C161 | 0.0290 (12) | 0.0240 (12) | 0.0321 (13) | 0.0056 (10) | 0.0048 (10) | 0.0066 (10) |
C162 | 0.084 (2) | 0.0459 (17) | 0.0301 (15) | 0.0381 (17) | 0.0083 (14) | 0.0076 (13) |
C163 | 0.099 (3) | 0.0473 (19) | 0.0444 (18) | 0.0448 (19) | 0.0145 (17) | 0.0029 (14) |
C164 | 0.0517 (17) | 0.0290 (14) | 0.0517 (17) | 0.0195 (13) | 0.0100 (14) | 0.0117 (13) |
C165 | 0.0433 (15) | 0.0298 (14) | 0.0424 (15) | 0.0106 (12) | 0.0099 (12) | 0.0164 (12) |
C166 | 0.0409 (14) | 0.0244 (13) | 0.0365 (14) | 0.0083 (11) | 0.0121 (12) | 0.0077 (11) |
C167 | 0.0362 (13) | 0.0250 (12) | 0.0284 (13) | 0.0118 (11) | 0.0060 (10) | 0.0056 (10) |
O16 | 0.0361 (9) | 0.0207 (8) | 0.0307 (9) | 0.0129 (7) | 0.0046 (7) | 0.0041 (7) |
C17 | 0.0285 (12) | 0.0233 (12) | 0.0256 (12) | 0.0072 (10) | 0.0055 (10) | 0.0035 (9) |
C18 | 0.0251 (12) | 0.0221 (12) | 0.0265 (12) | 0.0065 (10) | 0.0044 (10) | 0.0043 (9) |
C19 | 0.0281 (12) | 0.0262 (13) | 0.0267 (12) | 0.0077 (10) | 0.0055 (10) | 0.0071 (10) |
O191 | 0.0397 (11) | 0.0324 (10) | 0.0597 (12) | 0.0159 (9) | 0.0249 (9) | 0.0141 (9) |
O192 | 0.0383 (9) | 0.0176 (8) | 0.0425 (10) | 0.0088 (7) | 0.0170 (8) | 0.0050 (7) |
N21 | 0.0294 (10) | 0.0186 (10) | 0.0238 (10) | 0.0048 (8) | 0.0070 (8) | 0.0045 (8) |
C22 | 0.0253 (12) | 0.0213 (11) | 0.0215 (12) | 0.0030 (9) | 0.0053 (9) | 0.0068 (9) |
C210 | 0.0467 (17) | 0.0489 (17) | 0.0573 (18) | 0.0061 (14) | 0.0154 (14) | 0.0334 (15) |
C211 | 0.0438 (17) | 0.0467 (18) | 0.072 (2) | 0.0044 (14) | 0.0190 (15) | 0.0288 (16) |
C221 | 0.0347 (13) | 0.0221 (12) | 0.0155 (11) | 0.0040 (10) | −0.0009 (9) | 0.0032 (9) |
C222 | 0.0392 (14) | 0.0187 (12) | 0.0305 (13) | 0.0059 (10) | 0.0031 (11) | 0.0045 (10) |
C223 | 0.0468 (16) | 0.0302 (14) | 0.0325 (14) | 0.0160 (12) | 0.0046 (12) | 0.0031 (11) |
C224 | 0.0362 (14) | 0.0483 (17) | 0.0273 (13) | 0.0142 (13) | 0.0070 (11) | 0.0065 (12) |
C225 | 0.0414 (15) | 0.0369 (15) | 0.0258 (13) | 0.0025 (12) | 0.0072 (11) | 0.0081 (11) |
C226 | 0.0435 (15) | 0.0212 (12) | 0.0253 (12) | 0.0050 (11) | 0.0061 (11) | 0.0064 (10) |
C227 | 0.0336 (13) | 0.0205 (11) | 0.0209 (11) | 0.0052 (10) | 0.0006 (10) | 0.0003 (9) |
N22 | 0.0375 (11) | 0.0226 (10) | 0.0232 (10) | 0.0099 (9) | 0.0046 (9) | 0.0069 (8) |
N23 | 0.0296 (10) | 0.0192 (9) | 0.0229 (10) | 0.0061 (8) | 0.0050 (8) | 0.0073 (8) |
C24 | 0.0243 (11) | 0.0206 (11) | 0.0228 (12) | 0.0049 (9) | 0.0057 (9) | 0.0066 (9) |
N24 | 0.0353 (11) | 0.0205 (10) | 0.0204 (10) | 0.0087 (8) | 0.0044 (8) | 0.0066 (8) |
C25 | 0.0269 (12) | 0.0186 (11) | 0.0215 (11) | 0.0044 (9) | 0.0047 (9) | 0.0045 (9) |
N25 | 0.0345 (11) | 0.0271 (11) | 0.0259 (11) | 0.0083 (9) | 0.0066 (9) | 0.0086 (8) |
O25 | 0.0498 (11) | 0.0297 (9) | 0.0253 (9) | 0.0170 (8) | 0.0054 (8) | 0.0095 (7) |
C26 | 0.0255 (12) | 0.0178 (11) | 0.0251 (12) | 0.0017 (9) | 0.0061 (10) | 0.0050 (9) |
C261 | 0.0278 (12) | 0.0180 (11) | 0.0260 (12) | 0.0013 (9) | 0.0052 (10) | 0.0052 (9) |
C262 | 0.0500 (16) | 0.0255 (13) | 0.0274 (13) | 0.0147 (12) | 0.0094 (11) | 0.0092 (10) |
C263 | 0.0547 (17) | 0.0297 (14) | 0.0386 (15) | 0.0209 (13) | 0.0125 (13) | 0.0108 (11) |
C264 | 0.0512 (16) | 0.0289 (14) | 0.0327 (14) | 0.0114 (12) | 0.0157 (12) | 0.0030 (11) |
C265 | 0.0460 (15) | 0.0301 (13) | 0.0256 (13) | 0.0078 (12) | 0.0095 (11) | 0.0087 (10) |
C266 | 0.0386 (14) | 0.0216 (12) | 0.0277 (13) | 0.0074 (10) | 0.0062 (10) | 0.0062 (10) |
C267 | 0.0374 (13) | 0.0196 (11) | 0.0290 (12) | 0.0091 (10) | 0.0061 (10) | 0.0090 (10) |
O26 | 0.0380 (9) | 0.0181 (8) | 0.0256 (8) | 0.0083 (7) | 0.0037 (7) | 0.0031 (7) |
C27 | 0.0332 (13) | 0.0229 (12) | 0.0239 (12) | 0.0115 (10) | 0.0099 (10) | 0.0061 (9) |
C28 | 0.0328 (13) | 0.0241 (12) | 0.0283 (13) | 0.0073 (10) | 0.0042 (10) | 0.0053 (10) |
C29 | 0.0310 (13) | 0.0194 (12) | 0.0377 (14) | 0.0074 (10) | 0.0104 (11) | 0.0081 (10) |
O291 | 0.0415 (11) | 0.0499 (12) | 0.0351 (10) | −0.0038 (9) | −0.0016 (9) | 0.0217 (9) |
O292 | 0.0341 (9) | 0.0283 (9) | 0.0422 (10) | 0.0020 (8) | 0.0085 (8) | 0.0132 (8) |
Geometric parameters (Å, º) top
N11—C16 | 1.298 (3) | N21—C26 | 1.299 (3) |
N11—C12 | 1.376 (3) | N21—C22 | 1.378 (3) |
C12—N12 | 1.325 (3) | C22—N22 | 1.324 (3) |
C12—N13 | 1.345 (3) | C22—N23 | 1.341 (3) |
C110—O192 | 1.446 (3) | C210—O292 | 1.454 (3) |
C110—C111 | 1.496 (4) | C210—C211 | 1.491 (4) |
C110—H11A | 0.9900 | C210—H21A | 0.9900 |
C110—H11B | 0.9900 | C210—H21B | 0.9900 |
C111—H11C | 0.9800 | C211—H21C | 0.9800 |
C111—H11D | 0.9800 | C211—H21D | 0.9800 |
C111—H11E | 0.9800 | C211—H21E | 0.9800 |
C121—C126 | 1.376 (3) | C221—C226 | 1.396 (3) |
C121—C122 | 1.389 (3) | C221—C222 | 1.396 (3) |
C121—C127 | 1.517 (3) | C221—C227 | 1.505 (3) |
C122—C123 | 1.396 (3) | C222—C223 | 1.383 (4) |
C122—H122 | 0.9500 | C222—H222 | 0.9500 |
C123—C124 | 1.372 (4) | C223—C224 | 1.385 (4) |
C123—H123 | 0.9500 | C223—H223 | 0.9500 |
C124—C125 | 1.375 (4) | C224—C225 | 1.393 (4) |
C124—H124 | 0.9500 | C224—H224 | 0.9500 |
C125—C126 | 1.395 (3) | C225—C226 | 1.371 (4) |
C125—H125 | 0.9500 | C225—H225 | 0.9500 |
C126—H126 | 0.9500 | C226—H226 | 0.9500 |
C127—N12 | 1.455 (3) | C227—N22 | 1.463 (3) |
C127—H12A | 0.9900 | C227—H22A | 0.9900 |
C127—H12B | 0.9900 | C227—H22B | 0.9900 |
N12—H12 | 0.8800 | N22—H22 | 0.8800 |
N13—C14 | 1.330 (3) | N23—C24 | 1.332 (3) |
N14—C14 | 1.335 (3) | C24—N24 | 1.335 (3) |
N14—C17 | 1.455 (3) | C24—C25 | 1.446 (3) |
N14—H14 | 0.8800 | N24—C27 | 1.456 (3) |
C14—C15 | 1.448 (3) | N24—H24 | 0.8800 |
C15—N15 | 1.340 (3) | C25—N25 | 1.345 (3) |
C15—C16 | 1.440 (3) | C25—C26 | 1.435 (3) |
N15—O15 | 1.294 (2) | N25—O25 | 1.288 (2) |
C16—O16 | 1.336 (3) | C26—O26 | 1.339 (3) |
C161—C166 | 1.377 (3) | C261—C266 | 1.378 (3) |
C161—C162 | 1.386 (4) | C261—C262 | 1.395 (3) |
C161—C167 | 1.505 (3) | C261—C267 | 1.507 (3) |
C162—C163 | 1.381 (4) | C262—C263 | 1.377 (3) |
C162—H162 | 0.9500 | C262—H262 | 0.9500 |
C163—C164 | 1.372 (4) | C263—C264 | 1.382 (3) |
C163—H163 | 0.9500 | C263—H263 | 0.9500 |
C164—C165 | 1.367 (4) | C264—C265 | 1.380 (3) |
C164—H164 | 0.9500 | C264—H264 | 0.9500 |
C165—C166 | 1.397 (3) | C265—C266 | 1.385 (3) |
C165—H165 | 0.9500 | C265—H265 | 0.9500 |
C166—H166 | 0.9500 | C266—H266 | 0.9500 |
C167—O16 | 1.438 (3) | C267—O26 | 1.448 (2) |
C167—H16A | 0.9900 | C267—H26A | 0.9900 |
C167—H16B | 0.9900 | C267—H26B | 0.9900 |
C17—C18 | 1.517 (3) | C27—C28 | 1.518 (3) |
C17—H17A | 0.9900 | C27—H27A | 0.9900 |
C17—H17B | 0.9900 | C27—H27B | 0.9900 |
C18—C19 | 1.499 (3) | C28—C29 | 1.496 (3) |
C18—H18A | 0.9900 | C28—H28A | 0.9900 |
C18—H18B | 0.9900 | C28—H28B | 0.9900 |
C19—O191 | 1.195 (3) | C29—O291 | 1.204 (3) |
C19—O192 | 1.349 (3) | C29—O292 | 1.340 (3) |
| | | |
C16—N11—C12 | 115.32 (19) | C26—N21—C22 | 115.11 (18) |
N12—C12—N13 | 117.10 (19) | N22—C22—N23 | 116.8 (2) |
N12—C12—N11 | 115.47 (19) | N22—C22—N21 | 115.66 (19) |
N13—C12—N11 | 127.44 (19) | N23—C22—N21 | 127.50 (19) |
O192—C110—C111 | 107.4 (2) | O292—C210—C211 | 107.4 (2) |
O192—C110—H11A | 110.2 | O292—C210—H21A | 110.2 |
C111—C110—H11A | 110.2 | C211—C210—H21A | 110.2 |
O192—C110—H11B | 110.2 | O292—C210—H21B | 110.2 |
C111—C110—H11B | 110.2 | C211—C210—H21B | 110.2 |
H11A—C110—H11B | 108.5 | H21A—C210—H21B | 108.5 |
C110—C111—H11C | 109.5 | C210—C211—H21C | 109.5 |
C110—C111—H11D | 109.5 | C210—C211—H21D | 109.5 |
H11C—C111—H11D | 109.5 | H21C—C211—H21D | 109.5 |
C110—C111—H11E | 109.5 | C210—C211—H21E | 109.5 |
H11C—C111—H11E | 109.5 | H21C—C211—H21E | 109.5 |
H11D—C111—H11E | 109.5 | H21D—C211—H21E | 109.5 |
C126—C121—C122 | 119.1 (2) | C226—C221—C222 | 117.8 (2) |
C126—C121—C127 | 120.4 (2) | C226—C221—C227 | 121.2 (2) |
C122—C121—C127 | 120.5 (2) | C222—C221—C227 | 120.9 (2) |
C121—C122—C123 | 120.1 (2) | C223—C222—C221 | 121.1 (2) |
C121—C122—H122 | 119.9 | C223—C222—H222 | 119.5 |
C123—C122—H122 | 119.9 | C221—C222—H222 | 119.5 |
C124—C123—C122 | 120.3 (2) | C222—C223—C224 | 120.6 (2) |
C124—C123—H123 | 119.9 | C222—C223—H223 | 119.7 |
C122—C123—H123 | 119.9 | C224—C223—H223 | 119.7 |
C123—C124—C125 | 119.9 (2) | C223—C224—C225 | 118.5 (2) |
C123—C124—H124 | 120.0 | C223—C224—H224 | 120.8 |
C125—C124—H124 | 120.0 | C225—C224—H224 | 120.8 |
C124—C125—C126 | 120.0 (2) | C226—C225—C224 | 121.1 (2) |
C124—C125—H125 | 120.0 | C226—C225—H225 | 119.4 |
C126—C125—H125 | 120.0 | C224—C225—H225 | 119.4 |
C121—C126—C125 | 120.7 (2) | C225—C226—C221 | 120.9 (2) |
C121—C126—H126 | 119.7 | C225—C226—H226 | 119.5 |
C125—C126—H126 | 119.7 | C221—C226—H226 | 119.5 |
N12—C127—C121 | 114.33 (18) | N22—C227—C221 | 113.71 (18) |
N12—C127—H12A | 108.7 | N22—C227—H22A | 108.8 |
C121—C127—H12A | 108.7 | C221—C227—H22A | 108.8 |
N12—C127—H12B | 108.7 | N22—C227—H22B | 108.8 |
C121—C127—H12B | 108.7 | C221—C227—H22B | 108.8 |
H12A—C127—H12B | 107.6 | H22A—C227—H22B | 107.7 |
C12—N12—C127 | 122.82 (19) | C22—N22—C227 | 122.56 (18) |
C12—N12—H12 | 118.6 | C22—N22—H22 | 118.7 |
C127—N12—H12 | 118.6 | C227—N22—H22 | 118.7 |
C14—N13—C12 | 116.64 (19) | C24—N23—C22 | 116.49 (19) |
C14—N14—C17 | 122.87 (18) | N23—C24—N24 | 117.91 (19) |
C14—N14—H14 | 118.6 | N23—C24—C25 | 122.12 (19) |
C17—N14—H14 | 118.6 | N24—C24—C25 | 119.96 (19) |
N13—C14—N14 | 118.5 (2) | C24—N24—C27 | 122.78 (18) |
N13—C14—C15 | 121.9 (2) | C24—N24—H24 | 118.6 |
N14—C14—C15 | 119.51 (19) | C27—N24—H24 | 118.6 |
N15—C15—C16 | 117.8 (2) | N25—C25—C26 | 117.43 (19) |
N15—C15—C14 | 127.8 (2) | N25—C25—C24 | 128.32 (19) |
C16—C15—C14 | 114.30 (18) | C26—C25—C24 | 114.16 (18) |
O15—N15—C15 | 116.92 (19) | O25—N25—C25 | 116.58 (19) |
N11—C16—O16 | 120.7 (2) | N21—C26—O26 | 120.71 (19) |
N11—C16—C15 | 124.3 (2) | N21—C26—C25 | 124.6 (2) |
O16—C16—C15 | 115.01 (18) | O26—C26—C25 | 114.68 (18) |
C166—C161—C162 | 118.5 (2) | C266—C261—C262 | 118.6 (2) |
C166—C161—C167 | 123.2 (2) | C266—C261—C267 | 123.7 (2) |
C162—C161—C167 | 118.3 (2) | C262—C261—C267 | 117.6 (2) |
C163—C162—C161 | 120.7 (3) | C263—C262—C261 | 120.4 (2) |
C163—C162—H162 | 119.6 | C263—C262—H262 | 119.8 |
C161—C162—H162 | 119.6 | C261—C262—H262 | 119.8 |
C164—C163—C162 | 120.4 (3) | C262—C263—C264 | 120.7 (2) |
C164—C163—H163 | 119.8 | C262—C263—H263 | 119.6 |
C162—C163—H163 | 119.8 | C264—C263—H263 | 119.6 |
C165—C164—C163 | 119.6 (2) | C265—C264—C263 | 119.0 (2) |
C165—C164—H164 | 120.2 | C265—C264—H264 | 120.5 |
C163—C164—H164 | 120.2 | C263—C264—H264 | 120.5 |
C164—C165—C166 | 120.3 (2) | C264—C265—C266 | 120.5 (2) |
C164—C165—H165 | 119.8 | C264—C265—H265 | 119.8 |
C166—C165—H165 | 119.8 | C266—C265—H265 | 119.8 |
C161—C166—C165 | 120.5 (2) | C261—C266—C265 | 120.8 (2) |
C161—C166—H166 | 119.8 | C261—C266—H266 | 119.6 |
C165—C166—H166 | 119.8 | C265—C266—H266 | 119.6 |
O16—C167—C161 | 108.49 (18) | O26—C267—C261 | 108.03 (17) |
O16—C167—H16A | 110.0 | O26—C267—H26A | 110.1 |
C161—C167—H16A | 110.0 | C261—C267—H26A | 110.1 |
O16—C167—H16B | 110.0 | O26—C267—H26B | 110.1 |
C161—C167—H16B | 110.0 | C261—C267—H26B | 110.1 |
H16A—C167—H16B | 108.4 | H26A—C267—H26B | 108.4 |
C16—O16—C167 | 117.30 (17) | C26—O26—C267 | 117.61 (17) |
N14—C17—C18 | 110.87 (18) | N24—C27—C28 | 112.49 (19) |
N14—C17—H17A | 109.5 | N24—C27—H27A | 109.1 |
C18—C17—H17A | 109.5 | C28—C27—H27A | 109.1 |
N14—C17—H17B | 109.5 | N24—C27—H27B | 109.1 |
C18—C17—H17B | 109.5 | C28—C27—H27B | 109.1 |
H17A—C17—H17B | 108.1 | H27A—C27—H27B | 107.8 |
C19—C18—C17 | 112.19 (18) | C29—C28—C27 | 112.72 (19) |
C19—C18—H18A | 109.2 | C29—C28—H28A | 109.0 |
C17—C18—H18A | 109.2 | C27—C28—H28A | 109.0 |
C19—C18—H18B | 109.2 | C29—C28—H28B | 109.0 |
C17—C18—H18B | 109.2 | C27—C28—H28B | 109.0 |
H18A—C18—H18B | 107.9 | H28A—C28—H28B | 107.8 |
O191—C19—O192 | 123.4 (2) | O291—C29—O292 | 123.7 (2) |
O191—C19—C18 | 126.3 (2) | O291—C29—C28 | 124.9 (2) |
O192—C19—C18 | 110.31 (19) | O292—C29—C28 | 111.46 (19) |
C19—O192—C110 | 115.80 (18) | C29—O292—C210 | 115.66 (19) |
| | | |
C16—N11—C12—N12 | 177.88 (19) | C26—N21—C22—N22 | −178.46 (19) |
C16—N11—C12—N13 | −2.2 (3) | C26—N21—C22—N23 | 0.2 (3) |
C126—C121—C122—C123 | 0.1 (3) | C226—C221—C222—C223 | 0.2 (3) |
C127—C121—C122—C123 | 178.3 (2) | C227—C221—C222—C223 | −177.9 (2) |
C121—C122—C123—C124 | 0.4 (3) | C221—C222—C223—C224 | −0.7 (4) |
C122—C123—C124—C125 | −0.4 (4) | C222—C223—C224—C225 | 0.3 (4) |
C123—C124—C125—C126 | −0.1 (4) | C223—C224—C225—C226 | 0.5 (4) |
C122—C121—C126—C125 | −0.6 (3) | C224—C225—C226—C221 | −1.0 (3) |
C127—C121—C126—C125 | −178.8 (2) | C222—C221—C226—C225 | 0.6 (3) |
C124—C125—C126—C121 | 0.6 (3) | C227—C221—C226—C225 | 178.7 (2) |
C126—C121—C127—N12 | −45.6 (3) | C226—C221—C227—N22 | 40.0 (3) |
C122—C121—C127—N12 | 136.2 (2) | C222—C221—C227—N22 | −142.0 (2) |
N13—C12—N12—C127 | 6.9 (3) | N23—C22—N22—C227 | −2.1 (3) |
N11—C12—N12—C127 | −173.18 (18) | N21—C22—N22—C227 | 176.67 (19) |
C121—C127—N12—C12 | −76.1 (3) | C221—C227—N22—C22 | 76.6 (3) |
N12—C12—N13—C14 | −179.26 (19) | N22—C22—N23—C24 | 177.04 (19) |
N11—C12—N13—C14 | 0.9 (3) | N21—C22—N23—C24 | −1.6 (3) |
C12—N13—C14—N14 | −179.72 (19) | C22—N23—C24—N24 | −176.36 (19) |
C12—N13—C14—C15 | 0.6 (3) | C22—N23—C24—C25 | 2.7 (3) |
C17—N14—C14—N13 | 5.1 (3) | N23—C24—N24—C27 | 2.3 (3) |
C17—N14—C14—C15 | −175.26 (19) | C25—C24—N24—C27 | −176.7 (2) |
N13—C14—C15—N15 | −177.9 (2) | N23—C24—C25—N25 | −178.8 (2) |
N14—C14—C15—N15 | 2.4 (3) | N24—C24—C25—N25 | 0.2 (4) |
N13—C14—C15—C16 | −0.6 (3) | N23—C24—C25—C26 | −2.4 (3) |
N14—C14—C15—C16 | 179.72 (19) | N24—C24—C25—C26 | 176.62 (19) |
C16—C15—N15—O15 | −178.75 (19) | C26—C25—N25—O25 | −177.20 (19) |
C14—C15—N15—O15 | −1.5 (3) | C24—C25—N25—O25 | −0.9 (3) |
C12—N11—C16—O16 | −177.08 (18) | C22—N21—C26—O26 | 177.54 (19) |
C12—N11—C16—C15 | 2.1 (3) | C22—N21—C26—C25 | 0.1 (3) |
N15—C15—C16—N11 | 176.7 (2) | N25—C25—C26—N21 | 177.8 (2) |
C14—C15—C16—N11 | −0.9 (3) | C24—C25—C26—N21 | 0.9 (3) |
N15—C15—C16—O16 | −4.0 (3) | N25—C25—C26—O26 | 0.2 (3) |
C14—C15—C16—O16 | 178.38 (18) | C24—C25—C26—O26 | −176.64 (18) |
C166—C161—C162—C163 | −0.7 (5) | C266—C261—C262—C263 | 0.1 (4) |
C167—C161—C162—C163 | 179.1 (3) | C267—C261—C262—C263 | −179.7 (2) |
C161—C162—C163—C164 | −0.4 (5) | C261—C262—C263—C264 | 0.5 (4) |
C162—C163—C164—C165 | 1.4 (5) | C262—C263—C264—C265 | −0.6 (4) |
C163—C164—C165—C166 | −1.3 (4) | C263—C264—C265—C266 | 0.0 (4) |
C162—C161—C166—C165 | 0.9 (4) | C262—C261—C266—C265 | −0.6 (4) |
C167—C161—C166—C165 | −178.9 (2) | C267—C261—C266—C265 | 179.1 (2) |
C164—C165—C166—C161 | 0.1 (4) | C264—C265—C266—C261 | 0.6 (4) |
C166—C161—C167—O16 | −0.1 (3) | C266—C261—C267—O26 | 0.5 (3) |
C162—C161—C167—O16 | −179.8 (2) | C262—C261—C267—O26 | −179.7 (2) |
N11—C16—O16—C167 | −1.2 (3) | N21—C26—O26—C267 | −3.9 (3) |
C15—C16—O16—C167 | 179.55 (19) | C25—C26—O26—C267 | 173.77 (18) |
C161—C167—O16—C16 | 172.60 (18) | C261—C267—O26—C26 | −164.12 (18) |
C14—N14—C17—C18 | 80.2 (3) | C24—N24—C27—C28 | 92.3 (2) |
N14—C17—C18—C19 | 168.10 (18) | N24—C27—C28—C29 | 69.8 (2) |
C17—C18—C19—O191 | 2.1 (3) | C27—C28—C29—O291 | 1.7 (3) |
C17—C18—C19—O192 | −177.63 (17) | C27—C28—C29—O292 | −179.13 (19) |
O191—C19—O192—C110 | −0.2 (3) | O291—C29—O292—C210 | −0.3 (4) |
C18—C19—O192—C110 | 179.51 (18) | C28—C29—O292—C210 | −179.5 (2) |
C111—C110—O192—C19 | 174.4 (2) | C211—C210—O292—C29 | −174.7 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N14—H14···O15 | 0.88 | 1.94 | 2.605 (3) | 131 |
N24—H24···O25 | 0.88 | 1.97 | 2.626 (2) | 131 |
N22—H22···O15 | 0.88 | 2.07 | 2.853 (3) | 148 |
N12—H12···O25i | 0.88 | 2.09 | 2.875 (2) | 149 |
Symmetry code: (i) x+1, y, z+1. |
(8) 4-Benzylamino-2, 6-bis(benzyloxy)-5-nitrosopyrimidine
top
Crystal data top
C25H22N4O3 | F(000) = 896 |
Mr = 426.47 | Dx = 1.356 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 14.6856 (5) Å | Cell parameters from 3748 reflections |
b = 7.7726 (2) Å | θ = 1.0–27.5° |
c = 18.5721 (8) Å | µ = 0.09 mm−1 |
β = 99.8847 (13)° | T = 150 K |
V = 2088.45 (13) Å3 | Block, blue |
Z = 4 | 0.55 × 0.30 × 0.20 mm |
Data collection top
Kappa-CCD diffractometer | 4516 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 3296 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
φ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 1.6° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −19→19 |
Tmin = 0.952, Tmax = 0.982 | k = −10→10 |
12659 measured reflections | l = −23→24 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0762P)2] where P = (Fo2 + 2Fc2)/3 |
4516 reflections | (Δ/σ)max < 0.001 |
289 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
Special details top
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm
[Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which
effectively corrects for absorption effects. High redundancy data were used in
the scaling program hence the 'multi-scan' code word was used. No transmission
coefficients are available from the program (only scale factors for each
frame). The scale factors in the experimental table are calculated from the
'size' command in the SHELXL97 input file. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.43514 (9) | 0.16792 (15) | 0.16313 (7) | 0.0242 (3) | |
O1 | 0.31952 (7) | 0.07676 (13) | 0.21623 (5) | 0.0261 (3) | |
C2 | 0.35082 (10) | 0.09446 (18) | 0.15333 (8) | 0.0219 (3) | |
C27 | 0.22778 (11) | 0.0022 (2) | 0.21259 (8) | 0.0261 (4) | |
C21 | 0.19932 (10) | 0.03258 (18) | 0.28516 (8) | 0.0236 (3) | |
C22 | 0.12115 (11) | 0.1294 (2) | 0.29029 (8) | 0.0281 (4) | |
C23 | 0.09477 (11) | 0.1594 (2) | 0.35703 (9) | 0.0311 (4) | |
C24 | 0.14670 (12) | 0.0927 (2) | 0.42013 (9) | 0.0312 (4) | |
C25 | 0.22444 (12) | −0.0032 (2) | 0.41601 (9) | 0.0313 (4) | |
C26 | 0.25072 (11) | −0.03397 (19) | 0.34911 (8) | 0.0266 (4) | |
N3 | 0.29821 (8) | 0.04188 (15) | 0.09267 (7) | 0.0226 (3) | |
N4 | 0.28347 (9) | 0.01416 (16) | −0.03202 (7) | 0.0248 (3) | |
C47 | 0.19410 (10) | −0.07359 (19) | −0.03837 (9) | 0.0264 (4) | |
C41 | 0.11406 (10) | 0.04965 (18) | −0.05604 (8) | 0.0238 (3) | |
C42 | 0.08642 (11) | 0.14954 (19) | −0.00150 (9) | 0.0277 (4) | |
C43 | 0.01281 (12) | 0.2617 (2) | −0.01754 (10) | 0.0349 (4) | |
C44 | −0.03421 (12) | 0.2755 (2) | −0.08847 (11) | 0.0382 (4) | |
C45 | −0.00747 (12) | 0.1782 (2) | −0.14326 (10) | 0.0372 (4) | |
C46 | 0.06618 (11) | 0.0657 (2) | −0.12697 (9) | 0.0300 (4) | |
C4 | 0.33259 (10) | 0.06754 (18) | 0.03050 (8) | 0.0219 (3) | |
C5 | 0.42021 (10) | 0.15134 (18) | 0.03175 (8) | 0.0228 (3) | |
N5 | 0.46003 (9) | 0.19294 (17) | −0.02671 (7) | 0.0296 (3) | |
O5 | 0.41633 (8) | 0.15117 (15) | −0.08944 (6) | 0.0349 (3) | |
C6 | 0.46822 (10) | 0.19524 (18) | 0.10270 (8) | 0.0222 (3) | |
O6 | 0.55135 (7) | 0.26660 (14) | 0.10635 (6) | 0.0272 (3) | |
C67 | 0.59712 (11) | 0.3188 (2) | 0.17874 (9) | 0.0307 (4) | |
C61 | 0.69605 (10) | 0.36092 (18) | 0.17546 (8) | 0.0237 (3) | |
C62 | 0.76445 (11) | 0.2924 (2) | 0.22820 (9) | 0.0306 (4) | |
C63 | 0.85648 (12) | 0.3358 (2) | 0.23021 (9) | 0.0339 (4) | |
C64 | 0.88094 (12) | 0.4455 (2) | 0.17856 (9) | 0.0317 (4) | |
C65 | 0.81326 (12) | 0.51391 (19) | 0.12521 (9) | 0.0299 (4) | |
C66 | 0.72119 (11) | 0.47310 (19) | 0.12385 (8) | 0.0257 (4) | |
H27A | 0.2294 | −0.1227 | 0.2023 | 0.031* | |
H27B | 0.1835 | 0.0575 | 0.1732 | 0.031* | |
H22 | 0.0853 | 0.1756 | 0.2472 | 0.034* | |
H23 | 0.0411 | 0.2257 | 0.3597 | 0.037* | |
H24 | 0.1287 | 0.1132 | 0.4662 | 0.037* | |
H25 | 0.2602 | −0.0486 | 0.4593 | 0.038* | |
H26 | 0.3042 | −0.1010 | 0.3468 | 0.032* | |
H4 | 0.3059 | 0.0325 | −0.0723 | 0.030* | |
H47A | 0.1904 | −0.1330 | 0.0082 | 0.032* | |
H47B | 0.1895 | −0.1619 | −0.0773 | 0.032* | |
H42 | 0.1185 | 0.1405 | 0.0473 | 0.033* | |
H43 | −0.0055 | 0.3293 | 0.0201 | 0.042* | |
H44 | −0.0851 | 0.3521 | −0.0995 | 0.046* | |
H45 | −0.0395 | 0.1884 | −0.1921 | 0.045* | |
H46 | 0.0843 | −0.0015 | −0.1649 | 0.036* | |
H67A | 0.5942 | 0.2245 | 0.2141 | 0.037* | |
H67B | 0.5658 | 0.4208 | 0.1951 | 0.037* | |
H62 | 0.7482 | 0.2147 | 0.2634 | 0.037* | |
H63 | 0.9027 | 0.2897 | 0.2673 | 0.041* | |
H64 | 0.9440 | 0.4742 | 0.1795 | 0.038* | |
H65 | 0.8300 | 0.5892 | 0.0894 | 0.036* | |
H66 | 0.6750 | 0.5219 | 0.0875 | 0.031* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0204 (7) | 0.0294 (7) | 0.0230 (7) | −0.0011 (5) | 0.0040 (5) | −0.0010 (5) |
O1 | 0.0218 (6) | 0.0356 (6) | 0.0216 (6) | −0.0054 (4) | 0.0057 (5) | 0.0001 (4) |
C2 | 0.0204 (8) | 0.0230 (7) | 0.0226 (8) | 0.0020 (6) | 0.0048 (6) | 0.0014 (6) |
C27 | 0.0217 (8) | 0.0318 (8) | 0.0249 (9) | −0.0061 (6) | 0.0045 (6) | 0.0005 (6) |
C21 | 0.0238 (8) | 0.0239 (7) | 0.0235 (8) | −0.0067 (6) | 0.0053 (6) | −0.0005 (6) |
C22 | 0.0260 (9) | 0.0327 (8) | 0.0246 (8) | −0.0009 (7) | 0.0018 (7) | 0.0021 (6) |
C23 | 0.0266 (9) | 0.0359 (9) | 0.0317 (9) | −0.0005 (7) | 0.0074 (7) | −0.0041 (7) |
C24 | 0.0343 (10) | 0.0368 (9) | 0.0242 (8) | −0.0073 (7) | 0.0100 (7) | −0.0043 (7) |
C25 | 0.0360 (10) | 0.0331 (8) | 0.0232 (9) | −0.0059 (7) | 0.0001 (7) | 0.0028 (6) |
C26 | 0.0244 (8) | 0.0259 (8) | 0.0289 (9) | −0.0025 (6) | 0.0031 (7) | 0.0008 (6) |
N3 | 0.0214 (7) | 0.0248 (6) | 0.0216 (7) | 0.0003 (5) | 0.0039 (5) | −0.0006 (5) |
N4 | 0.0205 (7) | 0.0321 (7) | 0.0219 (7) | −0.0016 (5) | 0.0039 (5) | −0.0032 (5) |
C47 | 0.0252 (9) | 0.0252 (8) | 0.0280 (9) | −0.0027 (6) | 0.0019 (7) | −0.0055 (6) |
C41 | 0.0207 (8) | 0.0237 (7) | 0.0267 (8) | −0.0066 (6) | 0.0031 (6) | 0.0011 (6) |
C42 | 0.0283 (9) | 0.0266 (8) | 0.0283 (9) | −0.0044 (7) | 0.0050 (7) | −0.0003 (6) |
C43 | 0.0329 (10) | 0.0301 (8) | 0.0442 (10) | −0.0004 (7) | 0.0139 (8) | 0.0003 (7) |
C44 | 0.0240 (9) | 0.0325 (9) | 0.0578 (12) | 0.0013 (7) | 0.0061 (9) | 0.0121 (8) |
C45 | 0.0300 (10) | 0.0398 (10) | 0.0379 (10) | −0.0066 (8) | −0.0050 (8) | 0.0092 (8) |
C46 | 0.0281 (9) | 0.0337 (8) | 0.0268 (9) | −0.0061 (7) | 0.0009 (7) | −0.0009 (7) |
C4 | 0.0201 (8) | 0.0218 (7) | 0.0239 (8) | 0.0044 (6) | 0.0041 (6) | −0.0009 (6) |
C5 | 0.0224 (8) | 0.0246 (7) | 0.0221 (8) | 0.0028 (6) | 0.0060 (6) | 0.0002 (6) |
N5 | 0.0302 (8) | 0.0351 (7) | 0.0235 (7) | 0.0027 (6) | 0.0043 (6) | 0.0000 (6) |
O5 | 0.0327 (7) | 0.0474 (7) | 0.0242 (6) | −0.0019 (5) | 0.0042 (5) | 0.0003 (5) |
C6 | 0.0186 (8) | 0.0224 (7) | 0.0257 (8) | 0.0010 (6) | 0.0040 (6) | 0.0011 (6) |
O6 | 0.0205 (6) | 0.0364 (6) | 0.0245 (6) | −0.0054 (5) | 0.0034 (5) | −0.0021 (4) |
C67 | 0.0236 (9) | 0.0439 (9) | 0.0241 (8) | −0.0037 (7) | 0.0029 (7) | −0.0048 (7) |
C61 | 0.0216 (8) | 0.0269 (7) | 0.0228 (8) | −0.0028 (6) | 0.0040 (6) | −0.0026 (6) |
C62 | 0.0287 (9) | 0.0348 (8) | 0.0278 (9) | −0.0006 (7) | 0.0035 (7) | 0.0096 (7) |
C63 | 0.0252 (9) | 0.0428 (10) | 0.0316 (9) | 0.0026 (7) | −0.0014 (7) | 0.0035 (7) |
C64 | 0.0229 (9) | 0.0396 (9) | 0.0332 (9) | −0.0074 (7) | 0.0065 (7) | −0.0067 (7) |
C65 | 0.0378 (10) | 0.0284 (8) | 0.0249 (9) | −0.0106 (7) | 0.0094 (7) | −0.0014 (6) |
C66 | 0.0305 (9) | 0.0245 (7) | 0.0209 (8) | −0.0003 (6) | 0.0006 (7) | −0.0007 (6) |
Geometric parameters (Å, º) top
N1—C6 | 1.3145 (18) | C42—H42 | 0.9500 |
N1—C2 | 1.3472 (19) | C43—C44 | 1.383 (3) |
O1—C2 | 1.3339 (17) | C43—H43 | 0.9500 |
O1—C27 | 1.4575 (18) | C44—C45 | 1.378 (3) |
C2—N3 | 1.3169 (19) | C44—H44 | 0.9500 |
C27—C21 | 1.497 (2) | C45—C46 | 1.383 (2) |
C27—H27A | 0.9900 | C45—H45 | 0.9500 |
C27—H27B | 0.9900 | C46—H46 | 0.9500 |
C21—C22 | 1.389 (2) | C4—C5 | 1.439 (2) |
C21—C26 | 1.393 (2) | C5—N5 | 1.3577 (19) |
C22—C23 | 1.381 (2) | C5—C6 | 1.425 (2) |
C22—H22 | 0.9500 | N5—O5 | 1.2720 (16) |
C23—C24 | 1.384 (2) | C6—O6 | 1.3321 (18) |
C23—H23 | 0.9500 | O6—C67 | 1.4537 (18) |
C24—C25 | 1.377 (2) | C67—C61 | 1.501 (2) |
C24—H24 | 0.9500 | C67—H67A | 0.9900 |
C25—C26 | 1.384 (2) | C67—H67B | 0.9900 |
C25—H25 | 0.9500 | C61—C62 | 1.384 (2) |
C26—H26 | 0.9500 | C61—C66 | 1.392 (2) |
N3—C4 | 1.3522 (19) | C62—C63 | 1.387 (2) |
N4—C4 | 1.3241 (19) | C62—H62 | 0.9500 |
N4—C47 | 1.4659 (19) | C63—C64 | 1.377 (2) |
N4—H4 | 0.8800 | C63—H63 | 0.9500 |
C47—C41 | 1.508 (2) | C64—C65 | 1.383 (2) |
C47—H47A | 0.9900 | C64—H64 | 0.9500 |
C47—H47B | 0.9900 | C65—C66 | 1.385 (2) |
C41—C46 | 1.388 (2) | C65—H65 | 0.9500 |
C41—C42 | 1.391 (2) | C66—H66 | 0.9500 |
C42—C43 | 1.381 (2) | | |
| | | |
C6—N1—C2 | 114.76 (12) | C42—C43—H43 | 120.0 |
C2—O1—C27 | 117.07 (11) | C44—C43—H43 | 120.0 |
N3—C2—O1 | 118.51 (13) | C45—C44—C43 | 120.15 (16) |
N3—C2—N1 | 129.63 (14) | C45—C44—H44 | 119.9 |
O1—C2—N1 | 111.85 (12) | C43—C44—H44 | 119.9 |
O1—C27—C21 | 107.11 (12) | C44—C45—C46 | 119.78 (16) |
O1—C27—H27A | 110.3 | C44—C45—H45 | 120.1 |
C21—C27—H27A | 110.3 | C46—C45—H45 | 120.1 |
O1—C27—H27B | 110.3 | C45—C46—C41 | 120.93 (16) |
C21—C27—H27B | 110.3 | C45—C46—H46 | 119.5 |
H27A—C27—H27B | 108.5 | C41—C46—H46 | 119.5 |
C22—C21—C26 | 118.41 (14) | N4—C4—N3 | 118.39 (13) |
C22—C21—C27 | 120.59 (13) | N4—C4—C5 | 120.47 (14) |
C26—C21—C27 | 121.00 (14) | N3—C4—C5 | 121.13 (13) |
C23—C22—C21 | 121.04 (14) | N5—C5—C6 | 118.02 (13) |
C23—C22—H22 | 119.5 | N5—C5—C4 | 126.99 (14) |
C21—C22—H22 | 119.5 | C6—C5—C4 | 114.99 (13) |
C22—C23—C24 | 119.88 (15) | O5—N5—C5 | 116.93 (13) |
C22—C23—H23 | 120.1 | N1—C6—O6 | 119.58 (13) |
C24—C23—H23 | 120.1 | N1—C6—C5 | 123.65 (13) |
C25—C24—C23 | 119.82 (15) | O6—C6—C5 | 116.77 (13) |
C25—C24—H24 | 120.1 | C6—O6—C67 | 115.94 (12) |
C23—C24—H24 | 120.1 | O6—C67—C61 | 108.70 (12) |
C24—C25—C26 | 120.34 (15) | O6—C67—H67A | 110.0 |
C24—C25—H25 | 119.8 | C61—C67—H67A | 110.0 |
C26—C25—H25 | 119.8 | O6—C67—H67B | 110.0 |
C25—C26—C21 | 120.52 (15) | C61—C67—H67B | 110.0 |
C25—C26—H26 | 119.7 | H67A—C67—H67B | 108.3 |
C21—C26—H26 | 119.7 | C62—C61—C66 | 118.85 (14) |
C2—N3—C4 | 115.75 (12) | C62—C61—C67 | 118.52 (14) |
C4—N4—C47 | 124.19 (13) | C66—C61—C67 | 122.54 (14) |
C4—N4—H4 | 117.9 | C61—C62—C63 | 120.73 (15) |
C47—N4—H4 | 117.9 | C61—C62—H62 | 119.6 |
N4—C47—C41 | 112.06 (12) | C63—C62—H62 | 119.6 |
N4—C47—H47A | 109.2 | C64—C63—C62 | 120.09 (15) |
C41—C47—H47A | 109.2 | C64—C63—H63 | 120.0 |
N4—C47—H47B | 109.2 | C62—C63—H63 | 120.0 |
C41—C47—H47B | 109.2 | C63—C64—C65 | 119.73 (15) |
H47A—C47—H47B | 107.9 | C63—C64—H64 | 120.1 |
C46—C41—C42 | 118.50 (15) | C65—C64—H64 | 120.1 |
C46—C41—C47 | 120.83 (14) | C64—C65—C66 | 120.27 (14) |
C42—C41—C47 | 120.67 (14) | C64—C65—H65 | 119.9 |
C43—C42—C41 | 120.72 (15) | C66—C65—H65 | 119.9 |
C43—C42—H42 | 119.6 | C65—C66—C61 | 120.31 (14) |
C41—C42—H42 | 119.6 | C65—C66—H66 | 119.8 |
C42—C43—C44 | 119.92 (17) | C61—C66—H66 | 119.8 |
| | | |
C27—O1—C2—N3 | −0.97 (19) | C47—N4—C4—C5 | 179.43 (13) |
C27—O1—C2—N1 | 178.64 (12) | C2—N3—C4—N4 | 178.70 (12) |
C6—N1—C2—N3 | 2.2 (2) | C2—N3—C4—C5 | −1.55 (19) |
C6—N1—C2—O1 | −177.39 (12) | N4—C4—C5—N5 | 3.5 (2) |
C2—O1—C27—C21 | −167.21 (12) | N3—C4—C5—N5 | −176.24 (13) |
O1—C27—C21—C22 | 119.08 (15) | N4—C4—C5—C6 | −177.16 (13) |
O1—C27—C21—C26 | −60.39 (17) | N3—C4—C5—C6 | 3.1 (2) |
C26—C21—C22—C23 | 0.1 (2) | C6—C5—N5—O5 | 179.40 (12) |
C27—C21—C22—C23 | −179.42 (14) | C4—C5—N5—O5 | −1.3 (2) |
C21—C22—C23—C24 | 0.1 (2) | C2—N1—C6—O6 | −179.67 (12) |
C22—C23—C24—C25 | 0.0 (2) | C2—N1—C6—C5 | −0.2 (2) |
C23—C24—C25—C26 | −0.2 (2) | N5—C5—C6—N1 | 177.20 (13) |
C24—C25—C26—C21 | 0.4 (2) | C4—C5—C6—N1 | −2.2 (2) |
C22—C21—C26—C25 | −0.3 (2) | N5—C5—C6—O6 | −3.3 (2) |
C27—C21—C26—C25 | 179.17 (13) | C4—C5—C6—O6 | 177.30 (12) |
O1—C2—N3—C4 | 178.25 (12) | N1—C6—O6—C67 | −3.61 (19) |
N1—C2—N3—C4 | −1.3 (2) | C5—C6—O6—C67 | 176.87 (13) |
C4—N4—C47—C41 | 95.06 (16) | C6—O6—C67—C61 | 168.22 (12) |
N4—C47—C41—C46 | 100.32 (16) | O6—C67—C61—C62 | −132.15 (14) |
N4—C47—C41—C42 | −79.83 (18) | O6—C67—C61—C66 | 51.29 (19) |
C46—C41—C42—C43 | 0.2 (2) | C66—C61—C62—C63 | 0.6 (2) |
C47—C41—C42—C43 | −179.63 (14) | C67—C61—C62—C63 | −176.05 (15) |
C41—C42—C43—C44 | 0.0 (2) | C61—C62—C63—C64 | −1.3 (3) |
C42—C43—C44—C45 | −0.4 (3) | C62—C63—C64—C65 | 0.8 (3) |
C43—C44—C45—C46 | 0.5 (3) | C63—C64—C65—C66 | 0.3 (2) |
C44—C45—C46—C41 | −0.3 (2) | C64—C65—C66—C61 | −1.0 (2) |
C42—C41—C46—C45 | −0.1 (2) | C62—C61—C66—C65 | 0.5 (2) |
C47—C41—C46—C45 | 179.76 (14) | C67—C61—C66—C65 | 177.04 (14) |
C47—N4—C4—N3 | −0.8 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O5 | 0.88 | 1.94 | 2.606 (2) | 132 |
C23—H23···O5i | 0.95 | 2.40 | 3.304 (2) | 159 |
Symmetry code: (i) x−1/2, −y+1/2, z+1/2. |
(9) 2-Benzylamino-4,6-bis(benzyloxy)-5-nitrosopyrimidine
top
Crystal data top
C25H22N4O3 | F(000) = 896 |
Mr = 426.47 | Dx = 1.320 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.8074 (3) Å | Cell parameters from 10763 reflections |
b = 15.8175 (5) Å | θ = 1.0–27.5° |
c = 10.2119 (5) Å | µ = 0.09 mm−1 |
β = 105.7490 (11)° | T = 150 K |
V = 2146.54 (13) Å3 | Prism, green |
Z = 4 | 0.30 × 0.24 × 0.12 mm |
Data collection top
Kappa-CCD diffractometer | 4857 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 3078 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.075 |
φ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 1.5° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −17→17 |
Tmin = 0.974, Tmax = 0.989 | k = −20→17 |
18529 measured reflections | l = −13→13 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0662P)2] where P = (Fo2 + 2Fc2)/3 |
4857 reflections | (Δ/σ)max < 0.001 |
289 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
Special details top
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm
[Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which
effectively corrects for absorption effects. High redundancy data were used in
the scaling program hence the 'multi-scan' code word was used. No transmission
coefficients are available from the program (only scale factors for each
frame). The scale factors in the experimental table are calculated from the
'size' command in the SHELXL97 input file. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.50015 (9) | 0.07931 (8) | 0.71271 (13) | 0.0292 (3) | |
C2 | 0.44359 (11) | 0.04696 (10) | 0.79069 (15) | 0.0255 (4) | |
N2 | 0.44874 (9) | −0.03624 (8) | 0.80871 (12) | 0.0288 (3) | |
C27 | 0.39516 (12) | −0.08108 (10) | 0.89206 (16) | 0.0297 (4) | |
C21 | 0.28385 (12) | −0.09128 (9) | 0.82721 (15) | 0.0259 (4) | |
C22 | 0.24601 (12) | −0.10293 (10) | 0.68817 (15) | 0.0314 (4) | |
C23 | 0.14445 (13) | −0.11537 (11) | 0.63036 (17) | 0.0371 (4) | |
C24 | 0.07894 (13) | −0.11672 (11) | 0.70990 (18) | 0.0391 (4) | |
C25 | 0.11585 (14) | −0.10532 (12) | 0.84851 (18) | 0.0430 (5) | |
C26 | 0.21739 (13) | −0.09243 (11) | 0.90681 (16) | 0.0359 (4) | |
N3 | 0.38383 (9) | 0.08991 (8) | 0.85227 (12) | 0.0260 (3) | |
C4 | 0.38463 (11) | 0.17287 (10) | 0.83976 (15) | 0.0257 (4) | |
O4 | 0.32632 (8) | 0.21897 (6) | 0.89488 (11) | 0.0307 (3) | |
C47 | 0.26184 (12) | 0.17548 (10) | 0.96309 (16) | 0.0293 (4) | |
C41 | 0.20379 (11) | 0.24149 (10) | 1.01514 (14) | 0.0274 (4) | |
C42 | 0.22755 (12) | 0.32645 (10) | 1.01768 (16) | 0.0325 (4) | |
C43 | 0.17441 (13) | 0.38493 (11) | 1.07158 (17) | 0.0383 (4) | |
C44 | 0.09707 (13) | 0.35963 (12) | 1.12310 (17) | 0.0393 (4) | |
C45 | 0.07141 (14) | 0.27519 (12) | 1.11936 (18) | 0.0429 (5) | |
C46 | 0.12455 (13) | 0.21646 (11) | 1.06500 (17) | 0.0371 (4) | |
C5 | 0.44612 (11) | 0.21630 (9) | 0.77017 (16) | 0.0269 (4) | |
N5 | 0.45786 (10) | 0.30110 (8) | 0.75387 (14) | 0.0325 (3) | |
O5 | 0.41075 (9) | 0.35166 (7) | 0.80862 (12) | 0.0390 (3) | |
C6 | 0.50100 (11) | 0.16199 (10) | 0.70490 (16) | 0.0278 (4) | |
O6 | 0.55547 (8) | 0.19977 (7) | 0.63249 (11) | 0.0348 (3) | |
C67 | 0.61012 (12) | 0.14607 (11) | 0.56116 (17) | 0.0346 (4) | |
C61 | 0.70814 (12) | 0.11442 (10) | 0.65098 (15) | 0.0302 (4) | |
C62 | 0.78388 (13) | 0.17051 (11) | 0.71259 (16) | 0.0353 (4) | |
C63 | 0.87612 (14) | 0.14156 (13) | 0.78880 (17) | 0.0422 (5) | |
C64 | 0.89430 (14) | 0.05579 (13) | 0.80209 (18) | 0.0453 (5) | |
C65 | 0.81958 (15) | −0.00022 (12) | 0.74110 (18) | 0.0482 (5) | |
C66 | 0.72629 (14) | 0.02845 (11) | 0.66715 (17) | 0.0386 (4) | |
H2 | 0.4864 | −0.0657 | 0.7683 | 0.035* | |
H27A | 0.4048 | −0.0503 | 0.9791 | 0.036* | |
H27B | 0.4255 | −0.1379 | 0.9135 | 0.036* | |
H22 | 0.2906 | −0.1023 | 0.6318 | 0.038* | |
H23 | 0.1198 | −0.1230 | 0.5348 | 0.044* | |
H24 | 0.0090 | −0.1254 | 0.6702 | 0.047* | |
H25 | 0.0710 | −0.1063 | 0.9044 | 0.052* | |
H26 | 0.2417 | −0.0843 | 1.0023 | 0.043* | |
H47A | 0.3027 | 0.1413 | 1.0395 | 0.035* | |
H47B | 0.2152 | 0.1373 | 0.8989 | 0.035* | |
H42 | 0.2808 | 0.3449 | 0.9821 | 0.039* | |
H43 | 0.1917 | 0.4431 | 1.0729 | 0.046* | |
H44 | 0.0614 | 0.4000 | 1.1611 | 0.047* | |
H45 | 0.0175 | 0.2572 | 1.1539 | 0.052* | |
H46 | 0.1063 | 0.1584 | 1.0620 | 0.045* | |
H67A | 0.6234 | 0.1784 | 0.4848 | 0.042* | |
H67B | 0.5674 | 0.0971 | 0.5222 | 0.042* | |
H62 | 0.7721 | 0.2296 | 0.7022 | 0.042* | |
H63 | 0.9271 | 0.1806 | 0.8321 | 0.051* | |
H64 | 0.9582 | 0.0356 | 0.8532 | 0.054* | |
H65 | 0.8322 | −0.0593 | 0.7499 | 0.058* | |
H66 | 0.6746 | −0.0108 | 0.6274 | 0.046* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0287 (8) | 0.0237 (8) | 0.0370 (8) | 0.0000 (6) | 0.0120 (6) | −0.0003 (6) |
C2 | 0.0221 (8) | 0.0230 (9) | 0.0290 (8) | −0.0013 (7) | 0.0032 (6) | −0.0029 (6) |
N2 | 0.0304 (8) | 0.0195 (7) | 0.0390 (8) | 0.0012 (6) | 0.0138 (6) | −0.0018 (6) |
C27 | 0.0331 (9) | 0.0216 (9) | 0.0337 (9) | 0.0015 (7) | 0.0079 (7) | 0.0011 (7) |
C21 | 0.0315 (9) | 0.0160 (8) | 0.0313 (8) | 0.0012 (7) | 0.0102 (7) | 0.0002 (6) |
C22 | 0.0343 (10) | 0.0325 (10) | 0.0301 (9) | −0.0023 (8) | 0.0132 (7) | 0.0002 (7) |
C23 | 0.0393 (11) | 0.0403 (11) | 0.0287 (9) | −0.0045 (8) | 0.0042 (7) | 0.0031 (7) |
C24 | 0.0299 (10) | 0.0416 (11) | 0.0438 (10) | −0.0016 (8) | 0.0066 (8) | 0.0026 (8) |
C25 | 0.0384 (11) | 0.0527 (13) | 0.0439 (10) | 0.0000 (9) | 0.0212 (8) | −0.0019 (9) |
C26 | 0.0381 (11) | 0.0417 (11) | 0.0297 (9) | −0.0020 (8) | 0.0121 (7) | −0.0039 (7) |
N3 | 0.0254 (7) | 0.0190 (7) | 0.0333 (7) | 0.0008 (6) | 0.0074 (5) | −0.0007 (5) |
C4 | 0.0224 (8) | 0.0233 (9) | 0.0301 (8) | 0.0025 (7) | 0.0048 (6) | −0.0023 (6) |
O4 | 0.0328 (7) | 0.0220 (6) | 0.0415 (7) | 0.0006 (5) | 0.0172 (5) | −0.0010 (5) |
C47 | 0.0319 (9) | 0.0254 (9) | 0.0327 (9) | −0.0034 (7) | 0.0122 (7) | 0.0007 (7) |
C41 | 0.0263 (9) | 0.0298 (9) | 0.0248 (8) | 0.0023 (7) | 0.0049 (6) | −0.0002 (7) |
C42 | 0.0300 (10) | 0.0298 (10) | 0.0380 (9) | −0.0007 (7) | 0.0100 (7) | −0.0032 (7) |
C43 | 0.0391 (11) | 0.0310 (10) | 0.0428 (10) | 0.0030 (8) | 0.0079 (8) | −0.0061 (8) |
C44 | 0.0386 (11) | 0.0462 (12) | 0.0331 (9) | 0.0129 (9) | 0.0097 (8) | −0.0045 (8) |
C45 | 0.0408 (11) | 0.0492 (13) | 0.0453 (11) | 0.0075 (9) | 0.0227 (9) | 0.0067 (9) |
C46 | 0.0391 (11) | 0.0333 (11) | 0.0428 (10) | 0.0020 (8) | 0.0178 (8) | 0.0056 (8) |
C5 | 0.0242 (9) | 0.0203 (9) | 0.0354 (9) | 0.0000 (7) | 0.0066 (7) | 0.0014 (6) |
N5 | 0.0320 (8) | 0.0230 (8) | 0.0411 (8) | 0.0007 (6) | 0.0074 (6) | 0.0001 (6) |
O5 | 0.0427 (8) | 0.0226 (7) | 0.0525 (7) | 0.0023 (6) | 0.0143 (6) | −0.0017 (5) |
C6 | 0.0237 (9) | 0.0256 (9) | 0.0338 (9) | −0.0009 (7) | 0.0073 (7) | 0.0022 (7) |
O6 | 0.0343 (7) | 0.0275 (7) | 0.0484 (7) | 0.0032 (5) | 0.0209 (6) | 0.0052 (5) |
C67 | 0.0364 (10) | 0.0355 (10) | 0.0371 (9) | 0.0027 (8) | 0.0188 (8) | 0.0005 (7) |
C61 | 0.0360 (10) | 0.0288 (10) | 0.0313 (9) | 0.0027 (8) | 0.0185 (7) | 0.0018 (7) |
C62 | 0.0402 (11) | 0.0279 (10) | 0.0419 (10) | 0.0007 (8) | 0.0180 (8) | 0.0030 (7) |
C63 | 0.0396 (11) | 0.0515 (13) | 0.0381 (10) | −0.0052 (9) | 0.0149 (8) | −0.0002 (8) |
C64 | 0.0459 (12) | 0.0547 (14) | 0.0379 (10) | 0.0194 (10) | 0.0158 (8) | 0.0080 (9) |
C65 | 0.0656 (14) | 0.0322 (11) | 0.0481 (11) | 0.0169 (10) | 0.0178 (10) | 0.0040 (9) |
C66 | 0.0484 (12) | 0.0275 (10) | 0.0421 (10) | −0.0001 (8) | 0.0160 (8) | −0.0007 (7) |
Geometric parameters (Å, º) top
N1—C6 | 1.311 (2) | C42—C43 | 1.384 (2) |
N1—C2 | 1.3577 (19) | C42—H42 | 0.9500 |
C2—N2 | 1.3280 (19) | C43—C44 | 1.372 (2) |
C2—N3 | 1.3489 (19) | C43—H43 | 0.9500 |
N2—C27 | 1.4548 (19) | C44—C45 | 1.380 (3) |
N2—H2 | 0.8800 | C44—H44 | 0.9500 |
C27—C21 | 1.508 (2) | C45—C46 | 1.390 (2) |
C27—H27A | 0.9900 | C45—H45 | 0.9500 |
C27—H27B | 0.9900 | C46—H46 | 0.9500 |
C21—C26 | 1.381 (2) | C5—N5 | 1.3667 (19) |
C21—C22 | 1.386 (2) | C5—C6 | 1.425 (2) |
C22—C23 | 1.380 (2) | N5—O5 | 1.2541 (17) |
C22—H22 | 0.9500 | C6—O6 | 1.3309 (18) |
C23—C24 | 1.370 (2) | O6—C67 | 1.4560 (18) |
C23—H23 | 0.9500 | C67—C61 | 1.500 (2) |
C24—C25 | 1.380 (2) | C67—H67A | 0.9900 |
C24—H24 | 0.9500 | C67—H67B | 0.9900 |
C25—C26 | 1.382 (2) | C61—C66 | 1.385 (2) |
C25—H25 | 0.9500 | C61—C62 | 1.386 (2) |
C26—H26 | 0.9500 | C62—C63 | 1.378 (2) |
N3—C4 | 1.3188 (19) | C62—H62 | 0.9500 |
C4—O4 | 1.3201 (18) | C63—C64 | 1.380 (3) |
C4—C5 | 1.423 (2) | C63—H63 | 0.9500 |
O4—C47 | 1.4448 (17) | C64—C65 | 1.374 (3) |
C47—C41 | 1.499 (2) | C64—H64 | 0.9500 |
C47—H47A | 0.9900 | C65—C66 | 1.381 (2) |
C47—H47B | 0.9900 | C65—H65 | 0.9500 |
C41—C42 | 1.382 (2) | C66—H66 | 0.9500 |
C41—C46 | 1.384 (2) | | |
| | | |
C6—N1—C2 | 115.33 (13) | C41—C42—H42 | 119.7 |
N2—C2—N3 | 116.81 (14) | C43—C42—H42 | 119.7 |
N2—C2—N1 | 115.91 (13) | C44—C43—C42 | 120.62 (17) |
N3—C2—N1 | 127.28 (14) | C44—C43—H43 | 119.7 |
C2—N2—C27 | 123.20 (13) | C42—C43—H43 | 119.7 |
C2—N2—H2 | 118.4 | C43—C44—C45 | 119.51 (16) |
C27—N2—H2 | 118.4 | C43—C44—H44 | 120.2 |
N2—C27—C21 | 114.50 (12) | C45—C44—H44 | 120.2 |
N2—C27—H27A | 108.6 | C44—C45—C46 | 119.92 (17) |
C21—C27—H27A | 108.6 | C44—C45—H45 | 120.0 |
N2—C27—H27B | 108.6 | C46—C45—H45 | 120.0 |
C21—C27—H27B | 108.6 | C41—C46—C45 | 120.77 (16) |
H27A—C27—H27B | 107.6 | C41—C46—H46 | 119.6 |
C26—C21—C22 | 118.38 (15) | C45—C46—H46 | 119.6 |
C26—C21—C27 | 120.24 (13) | N5—C5—C4 | 129.88 (14) |
C22—C21—C27 | 121.34 (14) | N5—C5—C6 | 116.04 (14) |
C23—C22—C21 | 120.94 (15) | C4—C5—C6 | 114.06 (14) |
C23—C22—H22 | 119.5 | O5—N5—C5 | 118.59 (13) |
C21—C22—H22 | 119.5 | N1—C6—O6 | 119.84 (14) |
C24—C23—C22 | 120.42 (15) | N1—C6—C5 | 123.95 (14) |
C24—C23—H23 | 119.8 | O6—C6—C5 | 116.21 (14) |
C22—C23—H23 | 119.8 | C6—O6—C67 | 117.63 (12) |
C23—C24—C25 | 119.12 (16) | O6—C67—C61 | 113.13 (13) |
C23—C24—H24 | 120.4 | O6—C67—H67A | 109.0 |
C25—C24—H24 | 120.4 | C61—C67—H67A | 109.0 |
C24—C25—C26 | 120.68 (16) | O6—C67—H67B | 109.0 |
C24—C25—H25 | 119.7 | C61—C67—H67B | 109.0 |
C26—C25—H25 | 119.7 | H67A—C67—H67B | 107.8 |
C21—C26—C25 | 120.46 (15) | C66—C61—C62 | 119.01 (16) |
C21—C26—H26 | 119.8 | C66—C61—C67 | 120.32 (15) |
C25—C26—H26 | 119.8 | C62—C61—C67 | 120.57 (15) |
C4—N3—C2 | 115.71 (13) | C63—C62—C61 | 120.77 (17) |
N3—C4—O4 | 119.10 (13) | C63—C62—H62 | 119.6 |
N3—C4—C5 | 123.40 (13) | C61—C62—H62 | 119.6 |
O4—C4—C5 | 117.51 (14) | C62—C63—C64 | 119.86 (18) |
C4—O4—C47 | 118.00 (12) | C62—C63—H63 | 120.1 |
O4—C47—C41 | 107.35 (13) | C64—C63—H63 | 120.1 |
O4—C47—H47A | 110.2 | C65—C64—C63 | 119.69 (17) |
C41—C47—H47A | 110.2 | C65—C64—H64 | 120.2 |
O4—C47—H47B | 110.2 | C63—C64—H64 | 120.2 |
C41—C47—H47B | 110.2 | C64—C65—C66 | 120.68 (18) |
H47A—C47—H47B | 108.5 | C64—C65—H65 | 119.7 |
C42—C41—C46 | 118.60 (15) | C66—C65—H65 | 119.7 |
C42—C41—C47 | 122.48 (14) | C65—C66—C61 | 119.97 (17) |
C46—C41—C47 | 118.91 (15) | C65—C66—H66 | 120.0 |
C41—C42—C43 | 120.56 (16) | C61—C66—H66 | 120.0 |
| | | |
C6—N1—C2—N2 | −174.59 (13) | C42—C41—C46—C45 | −1.4 (2) |
C6—N1—C2—N3 | 4.8 (2) | C47—C41—C46—C45 | 177.33 (15) |
N3—C2—N2—C27 | −1.1 (2) | C44—C45—C46—C41 | 0.5 (3) |
N1—C2—N2—C27 | 178.38 (13) | N3—C4—C5—N5 | −177.06 (14) |
C2—N2—C27—C21 | 75.42 (18) | O4—C4—C5—N5 | 2.5 (2) |
N2—C27—C21—C26 | −147.96 (15) | N3—C4—C5—C6 | 5.0 (2) |
N2—C27—C21—C22 | 34.5 (2) | O4—C4—C5—C6 | −175.50 (13) |
C26—C21—C22—C23 | 0.0 (2) | C4—C5—N5—O5 | 1.7 (2) |
C27—C21—C22—C23 | 177.56 (14) | C6—C5—N5—O5 | 179.60 (13) |
C21—C22—C23—C24 | −0.2 (3) | C2—N1—C6—O6 | 179.01 (13) |
C22—C23—C24—C25 | 0.1 (3) | C2—N1—C6—C5 | −1.0 (2) |
C23—C24—C25—C26 | 0.2 (3) | N5—C5—C6—N1 | 178.37 (14) |
C22—C21—C26—C25 | 0.3 (2) | C4—C5—C6—N1 | −3.4 (2) |
C27—C21—C26—C25 | −177.26 (15) | N5—C5—C6—O6 | −1.7 (2) |
C24—C25—C26—C21 | −0.4 (3) | C4—C5—C6—O6 | 176.58 (13) |
N2—C2—N3—C4 | 176.05 (13) | N1—C6—O6—C67 | 1.7 (2) |
N1—C2—N3—C4 | −3.4 (2) | C5—C6—O6—C67 | −178.23 (13) |
C2—N3—C4—O4 | 178.55 (13) | C6—O6—C67—C61 | −81.55 (18) |
C2—N3—C4—C5 | −1.9 (2) | O6—C67—C61—C66 | 121.65 (16) |
N3—C4—O4—C47 | −1.9 (2) | O6—C67—C61—C62 | −62.1 (2) |
C5—C4—O4—C47 | 178.60 (13) | C66—C61—C62—C63 | 0.1 (2) |
C4—O4—C47—C41 | −179.63 (12) | C67—C61—C62—C63 | −176.22 (15) |
O4—C47—C41—C42 | −11.8 (2) | C61—C62—C63—C64 | 1.2 (2) |
O4—C47—C41—C46 | 169.48 (13) | C62—C63—C64—C65 | −1.1 (3) |
C46—C41—C42—C43 | 1.3 (2) | C63—C64—C65—C66 | −0.3 (3) |
C47—C41—C42—C43 | −177.44 (15) | C64—C65—C66—C61 | 1.7 (3) |
C41—C42—C43—C44 | −0.2 (3) | C62—C61—C66—C65 | −1.5 (2) |
C42—C43—C44—C45 | −0.8 (3) | C67—C61—C66—C65 | 174.79 (16) |
C43—C44—C45—C46 | 0.7 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O5i | 0.88 | 2.22 | 3.099 (2) | 173 |
N2—H2···N5i | 0.88 | 2.28 | 3.023 (2) | 143 |
Symmetry code: (i) −x+1, y−1/2, −z+3/2. |
(10) 2-Amino-4,6-bis(benzyloxy)pyrimidine
top
Crystal data top
C18H17N3O2 | F(000) = 1296 |
Mr = 307.35 | Dx = 1.326 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 32.4902 (9) Å | Cell parameters from 3482 reflections |
b = 7.5034 (2) Å | θ = 2.5–27.5° |
c = 12.7804 (4) Å | µ = 0.09 mm−1 |
β = 98.8790 (16)° | T = 150 K |
V = 3078.36 (15) Å3 | Block, colourless |
Z = 8 | 0.40 × 0.40 × 0.26 mm |
Data collection top
Kappa-CCD diffractometer | 3482 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2677 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
φ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 2.5° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −40→42 |
Tmin = 0.965, Tmax = 0.977 | k = −8→9 |
13174 measured reflections | l = −16→15 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0613P)2 + 0.8375P] where P = (Fo2 + 2Fc2)/3 |
3482 reflections | (Δ/σ)max = 0.001 |
208 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Special details top
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm
[Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which
effectively corrects for absorption effects. High redundancy data were used in
the scaling program hence the 'multi-scan' code word was used. No transmission
coefficients are available from the program (only scale factors for each
frame). The scale factors in the experimental table are calculated from the
'size' command in the SHELXL97 input file. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.51399 (3) | 0.30144 (14) | −0.10795 (7) | 0.0216 (2) | |
C2 | 0.55011 (4) | 0.37611 (16) | −0.12195 (9) | 0.0211 (3) | |
N2 | 0.55466 (3) | 0.42003 (16) | −0.22163 (8) | 0.0272 (3) | |
N3 | 0.58237 (3) | 0.41632 (14) | −0.04514 (8) | 0.0220 (2) | |
C4 | 0.57639 (4) | 0.37325 (17) | 0.05097 (9) | 0.0212 (3) | |
O4 | 0.60729 (3) | 0.40530 (13) | 0.13291 (6) | 0.0263 (2) | |
C47 | 0.64548 (4) | 0.47886 (18) | 0.10783 (10) | 0.0261 (3) | |
C41 | 0.67596 (4) | 0.49060 (17) | 0.20885 (10) | 0.0243 (3) | |
C42 | 0.67281 (4) | 0.38366 (19) | 0.29557 (10) | 0.0299 (3) | |
C43 | 0.70229 (4) | 0.3945 (2) | 0.38634 (11) | 0.0366 (4) | |
C44 | 0.73511 (4) | 0.5120 (2) | 0.39122 (12) | 0.0403 (4) | |
C45 | 0.73852 (4) | 0.6191 (2) | 0.30552 (13) | 0.0421 (4) | |
C46 | 0.70906 (4) | 0.6093 (2) | 0.21481 (12) | 0.0336 (3) | |
C5 | 0.54043 (4) | 0.29522 (17) | 0.07708 (9) | 0.0216 (3) | |
C6 | 0.50982 (4) | 0.26317 (16) | −0.00809 (9) | 0.0200 (3) | |
O6 | 0.47240 (2) | 0.18894 (12) | −0.00159 (6) | 0.0242 (2) | |
C67 | 0.46354 (4) | 0.14564 (17) | 0.10187 (9) | 0.0227 (3) | |
C61 | 0.42053 (4) | 0.06749 (17) | 0.09185 (9) | 0.0219 (3) | |
C62 | 0.39349 (4) | 0.06184 (18) | −0.00354 (10) | 0.0272 (3) | |
C63 | 0.35409 (4) | −0.0129 (2) | −0.00843 (11) | 0.0336 (3) | |
C64 | 0.34146 (4) | −0.08177 (19) | 0.08176 (12) | 0.0335 (3) | |
C66 | 0.40735 (4) | −0.00204 (18) | 0.18197 (10) | 0.0279 (3) | |
C65 | 0.36809 (4) | −0.07632 (19) | 0.17698 (11) | 0.0320 (3) | |
H2A | 0.5343 | 0.3993 | −0.2742 | 0.033* | |
H2B | 0.5780 | 0.4695 | −0.2343 | 0.033* | |
H47A | 0.6404 | 0.5988 | 0.0762 | 0.031* | |
H47B | 0.6568 | 0.4015 | 0.0562 | 0.031* | |
H42 | 0.6503 | 0.3022 | 0.2929 | 0.036* | |
H43 | 0.6998 | 0.3204 | 0.4454 | 0.044* | |
H44 | 0.7553 | 0.5191 | 0.4534 | 0.048* | |
H45 | 0.7611 | 0.7001 | 0.3085 | 0.051* | |
H46 | 0.7115 | 0.6843 | 0.1562 | 0.040* | |
H5 | 0.5373 | 0.2665 | 0.1478 | 0.026* | |
H67A | 0.4653 | 0.2543 | 0.1462 | 0.027* | |
H67B | 0.4842 | 0.0587 | 0.1363 | 0.027* | |
H62 | 0.4020 | 0.1093 | −0.0658 | 0.033* | |
H63 | 0.3358 | −0.0167 | −0.0740 | 0.040* | |
H64 | 0.3145 | −0.1327 | 0.0782 | 0.040* | |
H66 | 0.4255 | 0.0015 | 0.2478 | 0.033* | |
H65 | 0.3595 | −0.1236 | 0.2391 | 0.038* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0217 (5) | 0.0231 (6) | 0.0198 (5) | 0.0003 (4) | 0.0025 (4) | 0.0004 (4) |
C2 | 0.0228 (6) | 0.0189 (6) | 0.0219 (6) | 0.0029 (5) | 0.0040 (5) | 0.0012 (5) |
N2 | 0.0243 (6) | 0.0363 (7) | 0.0208 (5) | −0.0046 (5) | 0.0029 (4) | 0.0052 (5) |
N3 | 0.0224 (5) | 0.0223 (6) | 0.0213 (5) | −0.0002 (4) | 0.0032 (4) | −0.0010 (4) |
C4 | 0.0210 (6) | 0.0203 (6) | 0.0218 (6) | 0.0020 (5) | 0.0016 (5) | −0.0034 (5) |
O4 | 0.0194 (4) | 0.0382 (6) | 0.0210 (4) | −0.0063 (4) | 0.0025 (3) | −0.0035 (4) |
C47 | 0.0220 (6) | 0.0288 (7) | 0.0283 (6) | −0.0043 (5) | 0.0063 (5) | −0.0009 (6) |
C41 | 0.0201 (6) | 0.0246 (7) | 0.0285 (6) | 0.0007 (5) | 0.0049 (5) | −0.0050 (5) |
C42 | 0.0241 (7) | 0.0336 (8) | 0.0316 (7) | −0.0037 (6) | 0.0031 (6) | 0.0006 (6) |
C43 | 0.0293 (7) | 0.0489 (10) | 0.0306 (7) | 0.0030 (7) | 0.0016 (6) | 0.0036 (6) |
C44 | 0.0246 (7) | 0.0571 (11) | 0.0363 (8) | 0.0010 (7) | −0.0045 (6) | −0.0096 (7) |
C45 | 0.0267 (7) | 0.0488 (10) | 0.0489 (9) | −0.0125 (7) | −0.0001 (7) | −0.0065 (8) |
C46 | 0.0276 (7) | 0.0347 (8) | 0.0383 (8) | −0.0079 (6) | 0.0042 (6) | 0.0004 (6) |
C5 | 0.0230 (6) | 0.0242 (7) | 0.0179 (5) | −0.0002 (5) | 0.0043 (5) | −0.0009 (5) |
C6 | 0.0207 (6) | 0.0170 (6) | 0.0228 (6) | 0.0022 (5) | 0.0047 (5) | −0.0004 (5) |
O6 | 0.0211 (4) | 0.0319 (5) | 0.0199 (4) | −0.0049 (4) | 0.0038 (3) | 0.0003 (4) |
C67 | 0.0254 (6) | 0.0233 (7) | 0.0196 (6) | −0.0010 (5) | 0.0041 (5) | −0.0008 (5) |
C61 | 0.0224 (6) | 0.0177 (6) | 0.0264 (6) | 0.0017 (5) | 0.0066 (5) | −0.0022 (5) |
C62 | 0.0255 (7) | 0.0277 (7) | 0.0285 (6) | 0.0008 (5) | 0.0042 (5) | 0.0032 (6) |
C63 | 0.0239 (7) | 0.0382 (9) | 0.0366 (7) | 0.0006 (6) | −0.0023 (6) | 0.0018 (6) |
C64 | 0.0222 (7) | 0.0323 (8) | 0.0466 (8) | −0.0022 (6) | 0.0077 (6) | 0.0009 (6) |
C66 | 0.0309 (7) | 0.0268 (7) | 0.0264 (6) | −0.0031 (6) | 0.0061 (5) | −0.0017 (5) |
C65 | 0.0329 (7) | 0.0299 (8) | 0.0356 (7) | −0.0036 (6) | 0.0136 (6) | 0.0023 (6) |
Geometric parameters (Å, º) top
N1—C6 | 1.3353 (15) | C45—C46 | 1.387 (2) |
N1—C2 | 1.3372 (16) | C45—H45 | 0.9500 |
C2—N2 | 1.3459 (15) | C46—H46 | 0.9500 |
C2—N3 | 1.3550 (15) | C5—C6 | 1.3776 (16) |
N2—H2A | 0.8800 | C5—H5 | 0.9500 |
N2—H2B | 0.8800 | C6—O6 | 1.3516 (14) |
N3—C4 | 1.3132 (16) | O6—C67 | 1.4332 (14) |
C4—O4 | 1.3556 (14) | C67—C61 | 1.5026 (17) |
C4—C5 | 1.3927 (18) | C67—H67A | 0.9900 |
O4—C47 | 1.4388 (15) | C67—H67B | 0.9900 |
C47—C41 | 1.5034 (17) | C61—C62 | 1.3890 (17) |
C47—H47A | 0.9900 | C61—C66 | 1.3909 (18) |
C47—H47B | 0.9900 | C62—C63 | 1.3904 (19) |
C41—C42 | 1.3848 (19) | C62—H62 | 0.9500 |
C41—C46 | 1.3892 (18) | C63—C64 | 1.382 (2) |
C42—C43 | 1.3881 (18) | C63—H63 | 0.9500 |
C42—H42 | 0.9500 | C64—C65 | 1.381 (2) |
C43—C44 | 1.378 (2) | C64—H64 | 0.9500 |
C43—H43 | 0.9500 | C66—C65 | 1.3843 (19) |
C44—C45 | 1.377 (2) | C66—H66 | 0.9500 |
C44—H44 | 0.9500 | C65—H65 | 0.9500 |
| | | |
C6—N1—C2 | 116.01 (10) | C45—C46—H46 | 119.7 |
N1—C2—N2 | 117.13 (10) | C41—C46—H46 | 119.7 |
N1—C2—N3 | 126.39 (11) | C6—C5—C4 | 114.46 (11) |
N2—C2—N3 | 116.46 (11) | C6—C5—H5 | 122.8 |
C2—N2—H2A | 120.0 | C4—C5—H5 | 122.8 |
C2—N2—H2B | 120.0 | N1—C6—O6 | 111.85 (10) |
H2A—N2—H2B | 120.0 | N1—C6—C5 | 123.40 (11) |
C4—N3—C2 | 114.41 (10) | O6—C6—C5 | 124.75 (10) |
N3—C4—O4 | 118.69 (11) | C6—O6—C67 | 117.43 (9) |
N3—C4—C5 | 125.33 (11) | O6—C67—C61 | 109.05 (9) |
O4—C4—C5 | 115.98 (10) | O6—C67—H67A | 109.9 |
C4—O4—C47 | 117.21 (9) | C61—C67—H67A | 109.9 |
O4—C47—C41 | 107.91 (10) | O6—C67—H67B | 109.9 |
O4—C47—H47A | 110.1 | C61—C67—H67B | 109.9 |
C41—C47—H47A | 110.1 | H67A—C67—H67B | 108.3 |
O4—C47—H47B | 110.1 | C62—C61—C66 | 118.78 (11) |
C41—C47—H47B | 110.1 | C62—C61—C67 | 122.72 (11) |
H47A—C47—H47B | 108.4 | C66—C61—C67 | 118.50 (11) |
C42—C41—C46 | 118.66 (12) | C61—C62—C63 | 120.33 (12) |
C42—C41—C47 | 122.22 (11) | C61—C62—H62 | 119.8 |
C46—C41—C47 | 119.10 (12) | C63—C62—H62 | 119.8 |
C41—C42—C43 | 120.56 (13) | C64—C63—C62 | 120.21 (12) |
C41—C42—H42 | 119.7 | C64—C63—H63 | 119.9 |
C43—C42—H42 | 119.7 | C62—C63—H63 | 119.9 |
C44—C43—C42 | 120.30 (14) | C65—C64—C63 | 119.85 (12) |
C44—C43—H43 | 119.8 | C65—C64—H64 | 120.1 |
C42—C43—H43 | 119.8 | C63—C64—H64 | 120.1 |
C45—C44—C43 | 119.64 (13) | C65—C66—C61 | 120.81 (12) |
C45—C44—H44 | 120.2 | C65—C66—H66 | 119.6 |
C43—C44—H44 | 120.2 | C61—C66—H66 | 119.6 |
C44—C45—C46 | 120.27 (14) | C64—C65—C66 | 120.01 (13) |
C44—C45—H45 | 119.9 | C64—C65—H65 | 120.0 |
C46—C45—H45 | 119.9 | C66—C65—H65 | 120.0 |
C45—C46—C41 | 120.57 (14) | | |
| | | |
C6—N1—C2—N2 | −178.39 (11) | N3—C4—C5—C6 | 0.26 (19) |
C6—N1—C2—N3 | −0.17 (19) | O4—C4—C5—C6 | −179.49 (10) |
N1—C2—N3—C4 | 0.95 (18) | C2—N1—C6—O6 | 179.78 (10) |
N2—C2—N3—C4 | 179.17 (11) | C2—N1—C6—C5 | −0.65 (18) |
C2—N3—C4—O4 | 178.78 (11) | C4—C5—C6—N1 | 0.62 (18) |
C2—N3—C4—C5 | −0.97 (18) | C4—C5—C6—O6 | −179.87 (11) |
N3—C4—O4—C47 | −2.34 (16) | N1—C6—O6—C67 | −178.43 (10) |
C5—C4—O4—C47 | 177.43 (11) | C5—C6—O6—C67 | 2.01 (17) |
C4—O4—C47—C41 | −175.99 (10) | C6—O6—C67—C61 | 179.24 (10) |
O4—C47—C41—C42 | 23.68 (17) | O6—C67—C61—C62 | −6.91 (17) |
O4—C47—C41—C46 | −158.05 (12) | O6—C67—C61—C66 | 173.05 (11) |
C46—C41—C42—C43 | −0.3 (2) | C66—C61—C62—C63 | −0.3 (2) |
C47—C41—C42—C43 | 177.98 (13) | C67—C61—C62—C63 | 179.66 (12) |
C41—C42—C43—C44 | 0.0 (2) | C61—C62—C63—C64 | 0.2 (2) |
C42—C43—C44—C45 | 0.1 (2) | C62—C63—C64—C65 | 0.0 (2) |
C43—C44—C45—C46 | 0.2 (2) | C62—C61—C66—C65 | 0.3 (2) |
C44—C45—C46—C41 | −0.5 (2) | C67—C61—C66—C65 | −179.70 (12) |
C42—C41—C46—C45 | 0.5 (2) | C63—C64—C65—C66 | 0.0 (2) |
C47—C41—C46—C45 | −177.80 (13) | C61—C66—C65—C64 | −0.1 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N1i | 0.88 | 2.13 | 3.002 (2) | 170 |
N2—H2B···O4ii | 0.88 | 2.27 | 3.013 (2) | 142 |
Symmetry codes: (i) −x+1, y, −z−1/2; (ii) x, −y+1, z−1/2. |
(11) 2-Amino-4,6-bis(pyrrolidino)-5-nitrosopyrimidine hydrate
top
Crystal data top
C24H38.20N12O3.10 | F(000) = 1164 |
Mr = 544.47 | Dx = 1.345 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 18.4687 (8) Å | Cell parameters from 4758 reflections |
b = 8.1067 (3) Å | θ = 1.3–25.0° |
c = 19.1880 (6) Å | µ = 0.10 mm−1 |
β = 110.580 (2)° | T = 150 K |
V = 2689.50 (17) Å3 | Plate, colourless |
Z = 4 | 0.20 × 0.20 × 0.07 mm |
Data collection top
Kappa-CCD diffractometer | 4758 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 3200 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.060 |
φ scans and ω scans with κ offsets | θmax = 25.0°, θmin = 1.3° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −21→21 |
Tmin = 0.981, Tmax = 0.993 | k = −8→9 |
50212 measured reflections | l = −22→22 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.076 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.236 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.1429P)2 + 1.8403P] where P = (Fo2 + 2Fc2)/3 |
4758 reflections | (Δ/σ)max < 0.001 |
391 parameters | Δρmax = 0.52 e Å−3 |
13 restraints | Δρmin = −0.35 e Å−3 |
Special details top
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm
[Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which
effectively corrects for absorption effects. High redundancy data were used in
the scaling program hence the 'multi-scan' code word was used. No transmission
coefficients are available from the program (only scale factors for each
frame). The scale factors in the experimental table are calculated from the
'size' command in the SHELXL97 input file. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
N11 | 0.19035 (14) | 0.8837 (3) | 0.07345 (12) | 0.0298 (6) | |
C12 | 0.12823 (18) | 0.8534 (4) | 0.01186 (16) | 0.0386 (8) | |
N12 | 0.13982 (17) | 0.8564 (5) | −0.05275 (14) | 0.0583 (10) | |
N13 | 0.05638 (16) | 0.8135 (4) | 0.00832 (14) | 0.0475 (8) | |
C14 | 0.04130 (17) | 0.8310 (4) | 0.07010 (16) | 0.0348 (7) | |
N14 | −0.02471 (15) | 0.7687 (4) | 0.07128 (15) | 0.0413 (7) | |
C141 | −0.0795 (2) | 0.6865 (5) | 0.0052 (2) | 0.0519 (10) | |
C142 | −0.1421 (2) | 0.6266 (8) | 0.0317 (3) | 0.0938 (19) | |
C14B | −0.0883 (12) | 0.5790 (13) | 0.1085 (7) | 0.046* | 0.20 |
C143 | −0.1020 (4) | 0.5981 (10) | 0.1135 (3) | 0.147 (6) | 0.80 |
C144 | −0.0439 (2) | 0.7350 (5) | 0.1381 (2) | 0.0641 (12) | |
C15 | 0.09546 (18) | 0.9172 (4) | 0.13320 (17) | 0.0357 (7) | |
N15A | 0.0817 (2) | 1.0183 (5) | 0.1835 (2) | 0.0406 (11) | 0.792 (7) |
O15A | 0.01189 (15) | 1.0505 (4) | 0.17611 (16) | 0.0486 (10) | 0.792 (7) |
N15B | 0.0543 (9) | 1.0309 (18) | 0.1523 (8) | 0.0406 (11) | 0.21 |
O15B | 0.0896 (6) | 1.1434 (19) | 0.1925 (6) | 0.0486 (10) | 0.21 |
C16 | 0.17468 (17) | 0.9140 (4) | 0.13551 (16) | 0.0324 (7) | |
N16 | 0.23457 (15) | 0.9401 (4) | 0.19765 (14) | 0.0409 (7) | |
C161 | 0.31478 (19) | 0.9370 (5) | 0.19899 (18) | 0.0470 (9) | |
C163 | 0.3151 (2) | 0.9155 (7) | 0.3228 (2) | 0.0724 (14) | |
C162 | 0.3621 (2) | 0.9811 (7) | 0.2789 (2) | 0.0732 (14) | |
C164 | 0.2324 (2) | 0.9560 (5) | 0.27375 (17) | 0.0524 (10) | |
N21 | 0.30211 (14) | 0.8908 (3) | −0.07253 (13) | 0.0289 (6) | |
C22 | 0.35854 (18) | 0.8190 (4) | −0.01434 (16) | 0.0336 (7) | |
N22 | 0.34027 (16) | 0.7839 (4) | 0.04550 (14) | 0.0473 (8) | |
N23 | 0.42884 (15) | 0.7696 (3) | −0.01199 (14) | 0.0377 (7) | |
C24 | 0.45242 (17) | 0.8242 (4) | −0.06643 (16) | 0.0304 (7) | |
N24 | 0.52247 (14) | 0.7748 (3) | −0.06330 (14) | 0.0337 (6) | |
C241 | 0.57193 (18) | 0.6725 (5) | −0.00080 (18) | 0.0411 (8) | |
C242 | 0.6496 (2) | 0.6778 (5) | −0.0101 (2) | 0.0506 (9) | |
C243 | 0.6288 (2) | 0.6893 (5) | −0.0928 (2) | 0.0571 (11) | |
C244 | 0.5594 (2) | 0.8051 (5) | −0.1178 (2) | 0.0494 (9) | |
C25 | 0.40426 (17) | 0.9355 (4) | −0.12318 (16) | 0.0315 (7) | |
N25A | 0.4435 (2) | 1.0449 (4) | −0.14877 (17) | 0.0387 (10) | 0.887 (7) |
O25A | 0.40845 (14) | 1.1702 (3) | −0.18357 (14) | 0.0434 (9) | 0.887 (7) |
N25B | 0.426 (2) | 1.011 (4) | −0.1744 (13) | 0.0387 (10) | 0.11 |
O25B | 0.4883 (12) | 1.056 (3) | −0.1715 (12) | 0.0434 (9) | 0.11 |
C26 | 0.32333 (17) | 0.9402 (3) | −0.12923 (15) | 0.0289 (7) | |
N26 | 0.26710 (15) | 0.9911 (3) | −0.19068 (13) | 0.0347 (6) | |
C261 | 0.18556 (18) | 0.9925 (4) | −0.19584 (17) | 0.0378 (8) | |
C262 | 0.1419 (2) | 1.0545 (5) | −0.27375 (18) | 0.0480 (9) | |
C263 | 0.1902 (2) | 0.9920 (5) | −0.31777 (18) | 0.0505 (10) | |
C264 | 0.2731 (2) | 1.0189 (5) | −0.26436 (17) | 0.0438 (9) | |
O1 | 0.45652 (16) | 0.6786 (5) | 0.18190 (16) | 0.0644 (13) | 0.902 (8) |
O2 | −0.0446 (8) | 0.310 (2) | 0.1852 (8) | 0.078 (5) | 0.20 |
H12A | 0.1016 | 0.8331 | −0.0943 | 0.070* | |
H12B | 0.1857 | 0.8817 | −0.0539 | 0.070* | |
H14A | −0.0545 | 0.5934 | −0.0109 | 0.062* | |
H14B | −0.1001 | 0.7651 | −0.0366 | 0.062* | |
H14C | −0.1706 | 0.5311 | 0.0027 | 0.113* | |
H14D | −0.1787 | 0.7150 | 0.0326 | 0.113* | |
H14F | −0.1178 | 0.5433 | 0.1401 | 0.055* | 0.20 |
H14E | −0.0532 | 0.4889 | 0.1059 | 0.055* | 0.20 |
H14I | −0.0761 | 0.4892 | 0.1228 | 0.176* | 0.80 |
H14J | −0.1392 | 0.6033 | 0.1400 | 0.176* | 0.80 |
H14H | −0.0765 | 0.8222 | 0.1481 | 0.077* | |
H14G | 0.0025 | 0.7156 | 0.1829 | 0.077* | |
H16A | 0.3224 | 1.0189 | 0.1639 | 0.056* | |
H16B | 0.3287 | 0.8262 | 0.1860 | 0.056* | |
H16E | 0.3291 | 0.9710 | 0.3717 | 0.087* | |
H16F | 0.3223 | 0.7950 | 0.3307 | 0.087* | |
H16D | 0.4136 | 0.9282 | 0.2947 | 0.088* | |
H16C | 0.3688 | 1.1021 | 0.2850 | 0.088* | |
H16H | 0.1953 | 0.8771 | 0.2820 | 0.063* | |
H16G | 0.2182 | 1.0694 | 0.2831 | 0.063* | |
H22A | 0.3735 | 0.7313 | 0.0834 | 0.057* | |
H22B | 0.2950 | 0.8133 | 0.0470 | 0.057* | |
H24A | 0.5522 | 0.5581 | −0.0045 | 0.049* | |
H24B | 0.5749 | 0.7198 | 0.0477 | 0.049* | |
H24D | 0.6799 | 0.7751 | 0.0152 | 0.061* | |
H24C | 0.6798 | 0.5765 | 0.0098 | 0.061* | |
H24E | 0.6150 | 0.5796 | −0.1164 | 0.068* | |
H24F | 0.6723 | 0.7350 | −0.1056 | 0.068* | |
H24H | 0.5760 | 0.9216 | −0.1164 | 0.059* | |
H24G | 0.5243 | 0.7780 | −0.1687 | 0.059* | |
H26A | 0.1781 | 1.0672 | −0.1581 | 0.045* | |
H26B | 0.1682 | 0.8803 | −0.1886 | 0.045* | |
H26D | 0.1388 | 1.1764 | −0.2750 | 0.058* | |
H26C | 0.0889 | 1.0084 | −0.2933 | 0.058* | |
H26E | 0.1798 | 1.0560 | −0.3642 | 0.061* | |
H26F | 0.1800 | 0.8738 | −0.3304 | 0.061* | |
H26H | 0.3090 | 0.9392 | −0.2740 | 0.053* | |
H26G | 0.2909 | 1.1324 | −0.2686 | 0.053* | |
H11 | 0.465 (3) | 0.643 (7) | 0.2340 (11) | 0.097* | 0.902 (8) |
H12 | 0.5056 (17) | 0.735 (6) | 0.185 (3) | 0.097* | 0.902 (8) |
H21 | −0.011 (9) | 0.214 (16) | 0.186 (10) | 0.094* | 0.20 |
H22 | −0.048 (13) | 0.33 (3) | 0.236 (5) | 0.094* | 0.20 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N11 | 0.0288 (13) | 0.0387 (14) | 0.0229 (12) | 0.0035 (11) | 0.0103 (10) | 0.0018 (10) |
C12 | 0.0362 (18) | 0.054 (2) | 0.0277 (16) | −0.0090 (15) | 0.0135 (13) | 0.0004 (14) |
N12 | 0.0438 (18) | 0.108 (3) | 0.0256 (14) | −0.0287 (18) | 0.0157 (13) | −0.0085 (15) |
N13 | 0.0399 (16) | 0.077 (2) | 0.0277 (14) | −0.0175 (15) | 0.0140 (12) | −0.0066 (13) |
C14 | 0.0276 (17) | 0.0473 (19) | 0.0296 (16) | 0.0029 (14) | 0.0104 (13) | 0.0021 (13) |
N14 | 0.0288 (14) | 0.0591 (18) | 0.0386 (15) | −0.0024 (13) | 0.0150 (12) | −0.0028 (13) |
C141 | 0.0327 (19) | 0.071 (3) | 0.048 (2) | −0.0123 (17) | 0.0096 (15) | −0.0060 (18) |
C142 | 0.046 (3) | 0.145 (5) | 0.100 (4) | −0.043 (3) | 0.039 (3) | −0.054 (4) |
C143 | 0.148 (8) | 0.235 (12) | 0.107 (6) | −0.138 (9) | 0.108 (6) | −0.087 (6) |
C144 | 0.047 (2) | 0.100 (3) | 0.061 (2) | −0.016 (2) | 0.038 (2) | −0.023 (2) |
C15 | 0.0333 (17) | 0.0429 (19) | 0.0334 (16) | 0.0047 (14) | 0.0149 (13) | −0.0036 (13) |
N15A | 0.039 (3) | 0.051 (2) | 0.034 (2) | 0.0127 (19) | 0.0157 (18) | 0.000 (2) |
O15A | 0.0289 (16) | 0.077 (2) | 0.0404 (17) | 0.0121 (14) | 0.0124 (12) | −0.0140 (14) |
N15B | 0.039 (3) | 0.051 (2) | 0.034 (2) | 0.0127 (19) | 0.0157 (18) | 0.000 (2) |
O15B | 0.0289 (16) | 0.077 (2) | 0.0404 (17) | 0.0121 (14) | 0.0124 (12) | −0.0140 (14) |
C16 | 0.0305 (17) | 0.0385 (17) | 0.0296 (16) | 0.0025 (13) | 0.0124 (13) | −0.0025 (13) |
N16 | 0.0318 (15) | 0.0644 (19) | 0.0268 (14) | −0.0025 (13) | 0.0109 (11) | −0.0078 (12) |
C161 | 0.0308 (18) | 0.070 (3) | 0.0378 (18) | −0.0045 (17) | 0.0095 (14) | −0.0053 (17) |
C163 | 0.065 (3) | 0.113 (4) | 0.0281 (19) | 0.018 (3) | 0.0027 (18) | −0.012 (2) |
C162 | 0.038 (2) | 0.117 (4) | 0.051 (2) | −0.001 (2) | −0.0014 (18) | −0.026 (2) |
C164 | 0.050 (2) | 0.079 (3) | 0.0283 (17) | −0.0028 (19) | 0.0134 (15) | −0.0105 (17) |
N21 | 0.0308 (13) | 0.0320 (13) | 0.0259 (12) | 0.0006 (11) | 0.0124 (10) | 0.0006 (10) |
C22 | 0.0366 (17) | 0.0381 (17) | 0.0279 (15) | 0.0067 (14) | 0.0134 (13) | 0.0016 (13) |
N22 | 0.0384 (16) | 0.075 (2) | 0.0331 (15) | 0.0246 (15) | 0.0190 (12) | 0.0182 (14) |
N23 | 0.0378 (15) | 0.0497 (17) | 0.0313 (13) | 0.0141 (13) | 0.0192 (12) | 0.0082 (12) |
C24 | 0.0304 (17) | 0.0310 (16) | 0.0315 (16) | −0.0019 (12) | 0.0130 (13) | −0.0038 (12) |
N24 | 0.0297 (14) | 0.0390 (15) | 0.0367 (14) | 0.0019 (11) | 0.0169 (11) | 0.0036 (11) |
C241 | 0.0301 (17) | 0.054 (2) | 0.0410 (18) | 0.0079 (15) | 0.0150 (14) | 0.0043 (15) |
C242 | 0.0366 (19) | 0.056 (2) | 0.065 (2) | 0.0061 (17) | 0.0264 (17) | 0.0050 (18) |
C243 | 0.060 (2) | 0.059 (2) | 0.072 (3) | 0.0125 (19) | 0.047 (2) | 0.008 (2) |
C244 | 0.050 (2) | 0.058 (2) | 0.056 (2) | 0.0078 (18) | 0.0371 (18) | 0.0099 (18) |
C25 | 0.0343 (17) | 0.0311 (16) | 0.0335 (16) | −0.0004 (13) | 0.0176 (13) | 0.0015 (12) |
N25A | 0.048 (2) | 0.035 (2) | 0.041 (2) | −0.0024 (14) | 0.0255 (19) | 0.0000 (15) |
O25A | 0.0395 (16) | 0.0413 (16) | 0.0514 (16) | 0.0032 (12) | 0.0186 (12) | 0.0148 (12) |
N25B | 0.048 (2) | 0.035 (2) | 0.041 (2) | −0.0024 (14) | 0.0255 (19) | 0.0000 (15) |
O25B | 0.0395 (16) | 0.0413 (16) | 0.0514 (16) | 0.0032 (12) | 0.0186 (12) | 0.0148 (12) |
C26 | 0.0322 (16) | 0.0263 (15) | 0.0302 (15) | 0.0006 (12) | 0.0134 (13) | 0.0020 (12) |
N26 | 0.0318 (15) | 0.0453 (16) | 0.0282 (13) | 0.0016 (12) | 0.0122 (11) | 0.0089 (11) |
C261 | 0.0340 (18) | 0.0475 (19) | 0.0325 (16) | 0.0018 (15) | 0.0123 (13) | 0.0057 (14) |
C262 | 0.0361 (19) | 0.059 (2) | 0.0427 (19) | −0.0014 (17) | 0.0065 (15) | 0.0124 (16) |
C263 | 0.060 (2) | 0.059 (2) | 0.0296 (17) | −0.0038 (19) | 0.0125 (16) | 0.0082 (16) |
C264 | 0.048 (2) | 0.055 (2) | 0.0319 (17) | 0.0040 (17) | 0.0184 (15) | 0.0112 (15) |
O1 | 0.0348 (17) | 0.105 (3) | 0.0509 (19) | −0.0032 (16) | 0.0124 (13) | 0.0390 (17) |
O2 | 0.040 (8) | 0.137 (15) | 0.056 (8) | −0.005 (8) | 0.015 (6) | −0.058 (9) |
Geometric parameters (Å, º) top
N11—C16 | 1.343 (4) | N21—C26 | 1.341 (4) |
N11—C12 | 1.349 (4) | N21—C22 | 1.362 (4) |
C12—N12 | 1.330 (4) | C22—N22 | 1.336 (4) |
C12—N13 | 1.344 (4) | C22—N23 | 1.344 (4) |
N12—H12A | 0.8800 | N22—H22A | 0.8800 |
N12—H12B | 0.8800 | N22—H22B | 0.8800 |
N13—C14 | 1.317 (4) | N23—C24 | 1.340 (4) |
C14—N14 | 1.327 (4) | C24—N24 | 1.335 (4) |
C14—C15 | 1.450 (4) | C24—C25 | 1.453 (4) |
N14—C144 | 1.471 (4) | N24—C244 | 1.456 (4) |
N14—C141 | 1.473 (4) | N24—C241 | 1.480 (4) |
C141—C142 | 1.498 (6) | C241—C242 | 1.507 (5) |
C141—H14A | 0.9900 | C241—H24A | 0.9900 |
C141—H14B | 0.9900 | C241—H24B | 0.9900 |
C142—C143 | 1.499 (5) | C242—C243 | 1.498 (5) |
C142—C14B | 1.510 (5) | C242—H24D | 0.9900 |
C142—H14C | 0.9900 | C242—H24C | 0.9900 |
C142—H14D | 0.9900 | C243—C244 | 1.524 (5) |
C14B—C144 | 1.505 (5) | C243—H24E | 0.9900 |
C14B—H14F | 0.9900 | C243—H24F | 0.9900 |
C14B—H14E | 0.9900 | C244—H24H | 0.9900 |
C143—C144 | 1.500 (4) | C244—H24G | 0.9900 |
C143—H14I | 0.9900 | C25—N25B | 1.334 (5) |
C143—H14J | 0.9900 | C25—N25A | 1.342 (4) |
C144—H14H | 0.9900 | C25—C26 | 1.458 (4) |
C144—H14G | 0.9900 | N25A—O25A | 1.262 (3) |
C15—N15B | 1.326 (5) | N25B—O25B | 1.19 (4) |
C15—N15A | 1.357 (5) | C26—N26 | 1.333 (4) |
C15—C16 | 1.448 (4) | N26—C264 | 1.474 (4) |
N15A—O15A | 1.273 (4) | N26—C261 | 1.474 (4) |
N15B—O15B | 1.22 (2) | C261—C262 | 1.513 (4) |
C16—N16 | 1.328 (4) | C261—H26A | 0.9900 |
N16—C161 | 1.473 (4) | C261—H26B | 0.9900 |
N16—C164 | 1.480 (4) | C262—C263 | 1.515 (5) |
C161—C162 | 1.516 (5) | C262—H26D | 0.9900 |
C161—H16A | 0.9900 | C262—H26C | 0.9900 |
C161—H16B | 0.9900 | C263—C264 | 1.529 (5) |
C163—C162 | 1.504 (6) | C263—H26E | 0.9900 |
C163—C164 | 1.521 (5) | C263—H26F | 0.9900 |
C163—H16E | 0.9900 | C264—H26H | 0.9900 |
C163—H16F | 0.9900 | C264—H26G | 0.9900 |
C162—H16D | 0.9900 | O1—H11 | 1.000 (2) |
C162—H16C | 0.9900 | O1—H12 | 1.000 (2) |
C164—H16H | 0.9900 | O2—H21 | 1.000 (5) |
C164—H16G | 0.9900 | O2—H22 | 1.000 (5) |
| | | |
C16—N11—C12 | 115.3 (3) | N16—C164—C163 | 102.9 (3) |
N12—C12—N13 | 115.9 (3) | N16—C164—H16H | 111.2 |
N12—C12—N11 | 116.6 (3) | C163—C164—H16H | 111.2 |
N13—C12—N11 | 127.5 (3) | N16—C164—H16G | 111.2 |
C12—N12—H12A | 120.0 | C163—C164—H16G | 111.2 |
C12—N12—H12B | 120.0 | H16H—C164—H16G | 109.1 |
H12A—N12—H12B | 120.0 | C26—N21—C22 | 115.8 (2) |
C14—N13—C12 | 116.5 (3) | N22—C22—N23 | 116.1 (3) |
N13—C14—N14 | 117.4 (3) | N22—C22—N21 | 116.4 (3) |
N13—C14—C15 | 120.1 (3) | N23—C22—N21 | 127.4 (3) |
N14—C14—C15 | 122.5 (3) | C22—N22—H22A | 120.0 |
C14—N14—C144 | 126.2 (3) | C22—N22—H22B | 120.0 |
C14—N14—C141 | 120.9 (3) | H22A—N22—H22B | 120.0 |
C144—N14—C141 | 111.3 (3) | C24—N23—C22 | 116.7 (3) |
N14—C141—C142 | 103.5 (3) | N24—C24—N23 | 116.2 (3) |
N14—C141—H14A | 111.1 | N24—C24—C25 | 123.2 (3) |
C142—C141—H14A | 111.1 | N23—C24—C25 | 120.6 (3) |
N14—C141—H14B | 111.1 | C24—N24—C244 | 127.5 (3) |
C142—C141—H14B | 111.1 | C24—N24—C241 | 121.1 (2) |
H14A—C141—H14B | 109.0 | C244—N24—C241 | 111.4 (3) |
C141—C142—C143 | 104.4 (4) | N24—C241—C242 | 103.3 (3) |
C141—C142—C14B | 95.3 (10) | N24—C241—H24A | 111.1 |
C143—C142—C14B | 12.9 (13) | C242—C241—H24A | 111.1 |
C141—C142—H14C | 112.7 | N24—C241—H24B | 111.1 |
C143—C142—H14C | 115.9 | C242—C241—H24B | 111.1 |
C14B—C142—H14C | 112.7 | H24A—C241—H24B | 109.1 |
C141—C142—H14D | 112.7 | C243—C242—C241 | 103.1 (3) |
C143—C142—H14D | 100.4 | C243—C242—H24D | 111.1 |
C14B—C142—H14D | 112.7 | C241—C242—H24D | 111.1 |
H14C—C142—H14D | 110.2 | C243—C242—H24C | 111.1 |
C144—C14B—C142 | 103.8 (5) | C241—C242—H24C | 111.1 |
C144—C14B—H14F | 111.0 | H24D—C242—H24C | 109.1 |
C142—C14B—H14F | 111.0 | C242—C243—C244 | 104.2 (3) |
C144—C14B—H14E | 111.0 | C242—C243—H24E | 110.9 |
C142—C14B—H14E | 111.0 | C244—C243—H24E | 110.9 |
H14F—C14B—H14E | 109.0 | C242—C243—H24F | 110.9 |
C142—C143—C144 | 104.6 (4) | C244—C243—H24F | 110.9 |
C142—C143—H14I | 110.8 | H24E—C243—H24F | 108.9 |
C144—C143—H14I | 110.8 | N24—C244—C243 | 103.0 (3) |
C142—C143—H14J | 110.8 | N24—C244—H24H | 111.2 |
C144—C143—H14J | 110.8 | C243—C244—H24H | 111.2 |
H14I—C143—H14J | 108.9 | N24—C244—H24G | 111.2 |
N14—C144—C143 | 103.2 (3) | C243—C244—H24G | 111.2 |
N14—C144—C14B | 95.4 (9) | H24H—C244—H24G | 109.1 |
C143—C144—C14B | 12.9 (13) | N25B—C25—N25A | 24.1 (13) |
N14—C144—H14H | 112.7 | N25B—C25—C24 | 124.9 (16) |
C143—C144—H14H | 100.0 | N25A—C25—C24 | 114.7 (3) |
C14B—C144—H14H | 112.7 | N25B—C25—C26 | 119.8 (16) |
N14—C144—H14G | 112.7 | N25A—C25—C26 | 128.6 (3) |
C143—C144—H14G | 117.5 | C24—C25—C26 | 114.6 (2) |
C14B—C144—H14G | 112.7 | O25A—N25A—C25 | 118.9 (3) |
H14H—C144—H14G | 110.2 | O25B—N25B—C25 | 130 (3) |
N15B—C15—N15A | 27.6 (6) | N26—C26—N21 | 116.8 (3) |
N15B—C15—C16 | 132.5 (9) | N26—C26—C25 | 122.4 (3) |
N15A—C15—C16 | 115.4 (3) | N21—C26—C25 | 120.8 (3) |
N15B—C15—C14 | 105.8 (8) | C26—N26—C264 | 126.7 (3) |
N15A—C15—C14 | 129.6 (3) | C26—N26—C261 | 121.4 (2) |
C16—C15—C14 | 114.2 (3) | C264—N26—C261 | 110.7 (2) |
O15A—N15A—C15 | 118.7 (3) | N26—C261—C262 | 104.2 (3) |
O15B—N15B—C15 | 117.5 (13) | N26—C261—H26A | 110.9 |
N16—C16—N11 | 117.0 (3) | C262—C261—H26A | 110.9 |
N16—C16—C15 | 122.6 (3) | N26—C261—H26B | 110.9 |
N11—C16—C15 | 120.4 (3) | C262—C261—H26B | 110.9 |
C16—N16—C161 | 121.9 (3) | H26A—C261—H26B | 108.9 |
C16—N16—C164 | 126.7 (3) | C261—C262—C263 | 103.1 (3) |
C161—N16—C164 | 111.1 (3) | C261—C262—H26D | 111.1 |
N16—C161—C162 | 103.4 (3) | C263—C262—H26D | 111.1 |
N16—C161—H16A | 111.1 | C261—C262—H26C | 111.1 |
C162—C161—H16A | 111.1 | C263—C262—H26C | 111.1 |
N16—C161—H16B | 111.1 | H26D—C262—H26C | 109.1 |
C162—C161—H16B | 111.1 | C262—C263—C264 | 103.0 (3) |
H16A—C161—H16B | 109.0 | C262—C263—H26E | 111.2 |
C162—C163—C164 | 103.2 (3) | C264—C263—H26E | 111.2 |
C162—C163—H16E | 111.1 | C262—C263—H26F | 111.2 |
C164—C163—H16E | 111.1 | C264—C263—H26F | 111.2 |
C162—C163—H16F | 111.1 | H26E—C263—H26F | 109.1 |
C164—C163—H16F | 111.1 | N26—C264—C263 | 103.1 (3) |
H16E—C163—H16F | 109.1 | N26—C264—H26H | 111.1 |
C163—C162—C161 | 104.0 (3) | C263—C264—H26H | 111.1 |
C163—C162—H16D | 111.0 | N26—C264—H26G | 111.1 |
C161—C162—H16D | 111.0 | C263—C264—H26G | 111.1 |
C163—C162—H16C | 111.0 | H26H—C264—H26G | 109.1 |
C161—C162—H16C | 111.0 | H11—O1—H12 | 105 (4) |
H16D—C162—H16C | 109.0 | H21—O2—H22 | 111.1 (8) |
| | | |
C16—N11—C12—N12 | 166.7 (3) | N16—C161—C162—C163 | 30.2 (4) |
C16—N11—C12—N13 | −16.3 (5) | C16—N16—C164—C163 | 158.3 (4) |
N12—C12—N13—C14 | −171.4 (3) | C161—N16—C164—C163 | −14.9 (4) |
N11—C12—N13—C14 | 11.7 (6) | C162—C163—C164—N16 | 33.3 (4) |
C12—N13—C14—N14 | −169.8 (3) | C26—N21—C22—N22 | 173.7 (3) |
C12—N13—C14—C15 | 10.9 (5) | C26—N21—C22—N23 | −11.0 (5) |
N13—C14—N14—C144 | 162.8 (3) | N22—C22—N23—C24 | −170.7 (3) |
C15—C14—N14—C144 | −17.9 (5) | N21—C22—N23—C24 | 14.0 (5) |
N13—C14—N14—C141 | −1.3 (5) | C22—N23—C24—N24 | 179.7 (3) |
C15—C14—N14—C141 | 178.0 (3) | C22—N23—C24—C25 | 1.9 (4) |
C14—N14—C141—C142 | 176.6 (4) | N23—C24—N24—C244 | 174.9 (3) |
C144—N14—C141—C142 | 10.3 (5) | C25—C24—N24—C244 | −7.3 (5) |
N14—C141—C142—C143 | −28.8 (6) | N23—C24—N24—C241 | −3.0 (4) |
N14—C141—C142—C14B | −38.0 (8) | C25—C24—N24—C241 | 174.8 (3) |
C141—C142—C14B—C144 | 55.4 (16) | C24—N24—C241—C242 | −167.9 (3) |
C143—C142—C14B—C144 | −80.3 (14) | C244—N24—C241—C242 | 13.9 (4) |
C141—C142—C143—C144 | 37.1 (7) | N24—C241—C242—C243 | −32.3 (4) |
C14B—C142—C143—C144 | 83.1 (16) | C241—C242—C243—C244 | 39.2 (4) |
C14—N14—C144—C143 | −153.2 (5) | C24—N24—C244—C243 | −168.1 (3) |
C141—N14—C144—C143 | 12.2 (6) | C241—N24—C244—C243 | 10.0 (4) |
C14—N14—C144—C14B | −142.7 (8) | C242—C243—C244—N24 | −30.3 (4) |
C141—N14—C144—C14B | 22.6 (9) | N24—C24—C25—N25B | −5.5 (17) |
C142—C143—C144—N14 | −30.0 (7) | N23—C24—C25—N25B | 172.2 (17) |
C142—C143—C144—C14B | −83.7 (16) | N24—C24—C25—N25A | −30.7 (4) |
C142—C14B—C144—N14 | −48.3 (15) | N23—C24—C25—N25A | 147.0 (3) |
C142—C14B—C144—C143 | 79.6 (14) | N24—C24—C25—C26 | 164.5 (3) |
N13—C14—C15—N15B | 127.8 (9) | N23—C24—C25—C26 | −17.8 (4) |
N14—C14—C15—N15B | −51.5 (9) | N25B—C25—N25A—O25A | 76 (4) |
N13—C14—C15—N15A | 143.7 (4) | C24—C25—N25A—O25A | −162.8 (3) |
N14—C14—C15—N15A | −35.5 (6) | C26—C25—N25A—O25A | −0.6 (5) |
N13—C14—C15—C16 | −25.8 (4) | N25A—C25—N25B—O25B | 41 (3) |
N14—C14—C15—C16 | 154.9 (3) | C24—C25—N25B—O25B | −31 (4) |
N15B—C15—N15A—O15A | 32.7 (19) | C26—C25—N25B—O25B | 160 (3) |
C16—C15—N15A—O15A | 167.4 (3) | C22—N21—C26—N26 | 171.6 (3) |
C14—C15—N15A—O15A | −2.0 (6) | C22—N21—C26—C25 | −7.7 (4) |
N15A—C15—N15B—O15B | 43.7 (14) | N25B—C25—C26—N26 | 12.2 (17) |
C16—C15—N15B—O15B | −17 (2) | N25A—C25—C26—N26 | 39.5 (5) |
C14—C15—N15B—O15B | −163.4 (13) | C24—C25—C26—N26 | −158.3 (3) |
C12—N11—C16—N16 | 178.3 (3) | N25B—C25—C26—N21 | −168.6 (16) |
C12—N11—C16—C15 | −1.7 (4) | N25A—C25—C26—N21 | −141.3 (3) |
N15B—C15—C16—N16 | 56.3 (11) | C24—C25—C26—N21 | 20.9 (4) |
N15A—C15—C16—N16 | 29.8 (5) | N21—C26—N26—C264 | −166.8 (3) |
C14—C15—C16—N16 | −159.1 (3) | C25—C26—N26—C264 | 12.4 (5) |
N15B—C15—C16—N11 | −123.7 (10) | N21—C26—N26—C261 | −0.1 (4) |
N15A—C15—C16—N11 | −150.3 (3) | C25—C26—N26—C261 | 179.1 (3) |
C14—C15—C16—N11 | 20.8 (4) | C26—N26—C261—C262 | −178.9 (3) |
N11—C16—N16—C161 | 0.3 (5) | C264—N26—C261—C262 | −10.3 (4) |
C15—C16—N16—C161 | −179.8 (3) | N26—C261—C262—C263 | 31.1 (4) |
N11—C16—N16—C164 | −172.2 (3) | C261—C262—C263—C264 | −40.1 (4) |
C15—C16—N16—C164 | 7.7 (5) | C26—N26—C264—C263 | 153.4 (3) |
C16—N16—C161—C162 | 177.1 (4) | C261—N26—C264—C263 | −14.5 (4) |
C164—N16—C161—C162 | −9.3 (4) | C262—C263—C264—N26 | 33.4 (4) |
C164—C163—C162—C161 | −39.8 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N12—H12B···N21 | 0.88 | 2.30 | 3.163 (4) | 166 |
N22—H22B···N11 | 0.88 | 2.24 | 3.107 (4) | 169 |
N12—H12A···O15Ai | 0.88 | 2.33 | 3.059 (4) | 140 |
N22—H22A···O1 | 0.88 | 2.02 | 2.870 (4) | 163 |
O1—H11···O15Aii | 1.00 | 1.79 | 2.779 (4) | 171 |
O1—H11···N15Aii | 1.00 | 2.29 | 3.184 (5) | 149 |
O1—H12···O25Aiii | 1.00 | 1.77 | 2.769 (4) | 176 |
O1—H12···N25Aiii | 1.00 | 2.24 | 3.109 (5) | 145 |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+1, −y+2, −z. |