Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620004131/ef3005sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620004131/ef30051sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620004131/ef30052sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620004131/ef30053sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620004131/ef30055sup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620004131/ef30056sup6.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229620004131/ef3005sup7.pdf | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229620004131/ef3005sup8.pdf | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229620004131/ef3005sup9.pdf | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620004131/ef30051sup10.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620004131/ef30052sup11.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620004131/ef30053sup12.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620004131/ef30055sup13.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620004131/ef30056sup14.cml |
CCDC references: 1992894; 1957707; 1957708; 1957709; 1957710
For all structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020).
C10H11N5 | F(000) = 848 |
Mr = 201.24 | Dx = 1.268 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.7107 Å |
a = 10.1953 (4) Å | Cell parameters from 3131 reflections |
b = 14.2866 (5) Å | θ = 3.4–26.5° |
c = 14.9027 (5) Å | µ = 0.08 mm−1 |
β = 103.845 (3)° | T = 295 K |
V = 2107.60 (13) Å3 | Prism, colourless |
Z = 8 | 0.35 × 0.2 × 0.2 mm |
Agilent Xcalibur Eos diffractometer | 4041 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3222 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
Detector resolution: 16.2413 pixels mm-1 | θmax = 26.5°, θmin = 3.4° |
ω scans | h = −11→12 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −17→12 |
Tmin = 0.906, Tmax = 1.000 | l = −17→18 |
8099 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0485P)2 + 0.3264P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
4041 reflections | Δρmax = 0.16 e Å−3 |
281 parameters | Δρmin = −0.18 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.29100 (14) | 0.55930 (9) | 0.56620 (9) | 0.0595 (4) | |
C2A | 0.3758 (2) | 0.61528 (12) | 0.53505 (13) | 0.0685 (5) | |
H2A | 0.4173 | 0.6634 | 0.5736 | 0.082* | |
C3A | 0.40551 (18) | 0.60682 (12) | 0.45105 (13) | 0.0643 (5) | |
H3A | 0.4652 | 0.6477 | 0.4328 | 0.077* | |
C4A | 0.34390 (16) | 0.53550 (12) | 0.39410 (12) | 0.0600 (4) | |
H4A | 0.3620 | 0.5273 | 0.3363 | 0.072* | |
C5A | 0.25616 (16) | 0.47675 (11) | 0.42275 (11) | 0.0541 (4) | |
H5A | 0.2137 | 0.4284 | 0.3850 | 0.065* | |
C6A | 0.23184 (14) | 0.49111 (10) | 0.50992 (10) | 0.0464 (3) | |
N7A | 0.14372 (13) | 0.43413 (9) | 0.54394 (9) | 0.0528 (3) | |
C7A | 0.11997 (19) | 0.44791 (13) | 0.63509 (11) | 0.0652 (5) | |
H7A | 0.0266 | 0.4630 | 0.6295 | 0.098* | |
H7B | 0.1755 | 0.4983 | 0.6656 | 0.098* | |
H7C | 0.1421 | 0.3916 | 0.6706 | 0.098* | |
N8A | 0.07932 (12) | 0.36620 (8) | 0.48537 (8) | 0.0460 (3) | |
C9A | −0.00148 (15) | 0.30931 (10) | 0.51143 (11) | 0.0472 (3) | |
H9A | −0.0168 | 0.3142 | 0.5703 | 0.057* | |
C10A | −0.06858 (13) | 0.23755 (9) | 0.44859 (10) | 0.0411 (3) | |
N11A | −0.06041 (11) | 0.23075 (8) | 0.35855 (8) | 0.0411 (3) | |
H11A | −0.0116 (17) | 0.2686 (12) | 0.3266 (12) | 0.064 (5)* | |
C12A | −0.13159 (14) | 0.15517 (10) | 0.32253 (11) | 0.0463 (3) | |
H12A | −0.1413 | 0.1355 | 0.2618 | 0.056* | |
N13A | −0.18627 (13) | 0.11179 (9) | 0.38249 (9) | 0.0517 (3) | |
C14A | −0.14698 (15) | 0.16375 (10) | 0.46165 (11) | 0.0498 (4) | |
H14A | −0.1706 | 0.1505 | 0.5169 | 0.060* | |
N1B | 0.76134 (11) | 0.50517 (9) | 0.11245 (8) | 0.0478 (3) | |
C2B | 0.79490 (16) | 0.57779 (12) | 0.06520 (11) | 0.0550 (4) | |
H2B | 0.8812 | 0.5784 | 0.0547 | 0.066* | |
C3B | 0.71148 (17) | 0.65028 (12) | 0.03179 (11) | 0.0574 (4) | |
H3B | 0.7398 | 0.6991 | −0.0003 | 0.069* | |
C4B | 0.58293 (17) | 0.64901 (11) | 0.04708 (11) | 0.0554 (4) | |
H4B | 0.5231 | 0.6975 | 0.0250 | 0.066* | |
C5B | 0.54352 (14) | 0.57650 (10) | 0.09463 (10) | 0.0477 (4) | |
H5B | 0.4576 | 0.5749 | 0.1058 | 0.057* | |
C6B | 0.63668 (13) | 0.50498 (10) | 0.12588 (9) | 0.0391 (3) | |
N7B | 0.60307 (11) | 0.42776 (8) | 0.17296 (8) | 0.0446 (3) | |
C7B | 0.69653 (14) | 0.35214 (11) | 0.20626 (12) | 0.0529 (4) | |
H7D | 0.7012 | 0.3414 | 0.2705 | 0.079* | |
H7E | 0.7845 | 0.3686 | 0.1986 | 0.079* | |
H7F | 0.6659 | 0.2963 | 0.1718 | 0.079* | |
N8B | 0.47252 (10) | 0.42396 (8) | 0.17907 (8) | 0.0407 (3) | |
C9B | 0.42794 (13) | 0.35244 (10) | 0.21386 (9) | 0.0416 (3) | |
H9B | 0.4848 | 0.3028 | 0.2373 | 0.050* | |
C10B | 0.28703 (13) | 0.35056 (9) | 0.21593 (9) | 0.0386 (3) | |
N11B | 0.19760 (11) | 0.42037 (9) | 0.17942 (8) | 0.0396 (3) | |
H11B | 0.2133 (16) | 0.4736 (12) | 0.1521 (11) | 0.055 (5)* | |
C12B | 0.07718 (14) | 0.39654 (11) | 0.19431 (10) | 0.0459 (3) | |
H12B | −0.0003 | 0.4329 | 0.1762 | 0.055* | |
N13B | 0.08147 (12) | 0.31597 (9) | 0.23748 (9) | 0.0510 (3) | |
C14B | 0.21332 (15) | 0.28725 (11) | 0.25122 (10) | 0.0476 (4) | |
H14B | 0.2476 | 0.2320 | 0.2807 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0704 (9) | 0.0473 (8) | 0.0561 (8) | −0.0145 (7) | 0.0061 (7) | −0.0095 (6) |
C2A | 0.0822 (12) | 0.0505 (10) | 0.0670 (11) | −0.0253 (9) | 0.0063 (9) | −0.0091 (9) |
C3A | 0.0661 (11) | 0.0537 (10) | 0.0694 (11) | −0.0170 (8) | 0.0093 (9) | 0.0027 (9) |
C4A | 0.0592 (10) | 0.0600 (10) | 0.0596 (10) | −0.0096 (8) | 0.0118 (8) | −0.0036 (8) |
C5A | 0.0535 (9) | 0.0511 (9) | 0.0562 (9) | −0.0121 (7) | 0.0102 (7) | −0.0125 (7) |
C6A | 0.0450 (8) | 0.0383 (8) | 0.0512 (8) | −0.0018 (6) | 0.0020 (6) | −0.0038 (6) |
N7A | 0.0622 (8) | 0.0462 (7) | 0.0497 (7) | −0.0135 (6) | 0.0128 (6) | −0.0121 (6) |
C7A | 0.0868 (13) | 0.0579 (10) | 0.0503 (9) | −0.0145 (9) | 0.0152 (9) | −0.0076 (8) |
N8A | 0.0471 (7) | 0.0376 (6) | 0.0518 (7) | −0.0047 (5) | 0.0087 (5) | −0.0065 (5) |
C9A | 0.0519 (8) | 0.0421 (8) | 0.0491 (8) | −0.0016 (7) | 0.0151 (7) | −0.0032 (7) |
C10A | 0.0411 (7) | 0.0343 (7) | 0.0503 (8) | 0.0004 (6) | 0.0159 (6) | 0.0018 (6) |
N11A | 0.0388 (6) | 0.0375 (6) | 0.0483 (7) | −0.0051 (5) | 0.0131 (5) | 0.0046 (5) |
C12A | 0.0451 (8) | 0.0449 (8) | 0.0500 (8) | −0.0059 (7) | 0.0134 (6) | −0.0033 (7) |
N13A | 0.0531 (7) | 0.0424 (7) | 0.0646 (8) | −0.0117 (6) | 0.0237 (6) | −0.0042 (6) |
C14A | 0.0560 (9) | 0.0439 (8) | 0.0564 (9) | −0.0074 (7) | 0.0268 (7) | −0.0008 (7) |
N1B | 0.0361 (6) | 0.0583 (8) | 0.0513 (7) | −0.0034 (6) | 0.0148 (5) | −0.0047 (6) |
C2B | 0.0467 (8) | 0.0675 (11) | 0.0545 (9) | −0.0137 (8) | 0.0195 (7) | −0.0062 (8) |
C3B | 0.0676 (11) | 0.0551 (10) | 0.0520 (9) | −0.0172 (8) | 0.0190 (8) | −0.0012 (8) |
C4B | 0.0620 (10) | 0.0444 (9) | 0.0593 (9) | 0.0012 (7) | 0.0135 (8) | 0.0025 (7) |
C5B | 0.0420 (8) | 0.0448 (8) | 0.0575 (9) | 0.0023 (7) | 0.0146 (7) | −0.0004 (7) |
C6B | 0.0354 (7) | 0.0428 (8) | 0.0384 (7) | −0.0025 (6) | 0.0077 (5) | −0.0065 (6) |
N7B | 0.0307 (6) | 0.0472 (7) | 0.0571 (7) | 0.0058 (5) | 0.0130 (5) | 0.0073 (6) |
C7B | 0.0390 (8) | 0.0521 (9) | 0.0684 (10) | 0.0102 (7) | 0.0146 (7) | 0.0057 (8) |
N8B | 0.0315 (6) | 0.0452 (7) | 0.0463 (6) | 0.0020 (5) | 0.0112 (5) | 0.0017 (5) |
C9B | 0.0401 (7) | 0.0416 (8) | 0.0428 (7) | 0.0044 (6) | 0.0089 (6) | 0.0029 (6) |
C10B | 0.0404 (7) | 0.0390 (7) | 0.0371 (7) | −0.0006 (6) | 0.0104 (5) | 0.0028 (6) |
N11B | 0.0372 (6) | 0.0404 (7) | 0.0435 (6) | −0.0009 (5) | 0.0143 (5) | 0.0061 (5) |
C12B | 0.0370 (7) | 0.0548 (9) | 0.0475 (8) | −0.0033 (7) | 0.0131 (6) | 0.0023 (7) |
N13B | 0.0470 (7) | 0.0585 (8) | 0.0500 (7) | −0.0128 (6) | 0.0164 (6) | 0.0054 (6) |
C14B | 0.0523 (9) | 0.0436 (8) | 0.0468 (8) | −0.0040 (7) | 0.0119 (6) | 0.0074 (7) |
N1A—C6A | 1.3319 (18) | N1B—C6B | 1.3330 (16) |
N1A—C2A | 1.339 (2) | N1B—C2B | 1.343 (2) |
C2A—C3A | 1.362 (3) | C2B—C3B | 1.357 (2) |
C2A—H2A | 0.9300 | C2B—H2B | 0.9300 |
C3A—C4A | 1.378 (2) | C3B—C4B | 1.383 (2) |
C3A—H3A | 0.9300 | C3B—H3B | 0.9300 |
C4A—C5A | 1.367 (2) | C4B—C5B | 1.369 (2) |
C4A—H4A | 0.9300 | C4B—H4B | 0.9300 |
C5A—C6A | 1.395 (2) | C5B—C6B | 1.3969 (19) |
C5A—H5A | 0.9300 | C5B—H5B | 0.9300 |
C6A—N7A | 1.3946 (19) | C6B—N7B | 1.3934 (17) |
N7A—N8A | 1.3640 (16) | N7B—N8B | 1.3567 (14) |
N7A—C7A | 1.449 (2) | N7B—C7B | 1.4475 (18) |
C7A—H7A | 0.9600 | C7B—H7D | 0.9600 |
C7A—H7B | 0.9600 | C7B—H7E | 0.9600 |
C7A—H7C | 0.9600 | C7B—H7F | 0.9600 |
N8A—C9A | 1.2819 (18) | N8B—C9B | 1.2776 (17) |
C9A—C10A | 1.445 (2) | C9B—C10B | 1.4445 (18) |
C9A—H9A | 0.9300 | C9B—H9B | 0.9300 |
C10A—C14A | 1.3649 (19) | C10B—C14B | 1.3596 (19) |
C10A—N11A | 1.3677 (18) | C10B—N11B | 1.3728 (18) |
N11A—C12A | 1.3395 (18) | N11B—C12B | 1.3427 (17) |
N11A—H11A | 0.938 (17) | N11B—H11B | 0.895 (17) |
C12A—N13A | 1.3160 (18) | C12B—N13B | 1.3143 (19) |
C12A—H12A | 0.9300 | C12B—H12B | 0.9300 |
N13A—C14A | 1.370 (2) | N13B—C14B | 1.3732 (19) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C6A—N1A—C2A | 116.81 (15) | C6B—N1B—C2B | 116.86 (13) |
N1A—C2A—C3A | 124.72 (16) | N1B—C2B—C3B | 124.46 (14) |
N1A—C2A—H2A | 117.6 | N1B—C2B—H2B | 117.8 |
C3A—C2A—H2A | 117.6 | C3B—C2B—H2B | 117.8 |
C2A—C3A—C4A | 117.57 (16) | C2B—C3B—C4B | 117.71 (15) |
C2A—C3A—H3A | 121.2 | C2B—C3B—H3B | 121.1 |
C4A—C3A—H3A | 121.2 | C4B—C3B—H3B | 121.1 |
C5A—C4A—C3A | 119.83 (17) | C5B—C4B—C3B | 120.16 (15) |
C5A—C4A—H4A | 120.1 | C5B—C4B—H4B | 119.9 |
C3A—C4A—H4A | 120.1 | C3B—C4B—H4B | 119.9 |
C4A—C5A—C6A | 118.42 (14) | C4B—C5B—C6B | 117.76 (14) |
C4A—C5A—H5A | 120.8 | C4B—C5B—H5B | 121.1 |
C6A—C5A—H5A | 120.8 | C6B—C5B—H5B | 121.1 |
N1A—C6A—N7A | 115.60 (14) | N1B—C6B—N7B | 115.81 (12) |
N1A—C6A—C5A | 122.65 (14) | N1B—C6B—C5B | 123.03 (13) |
N7A—C6A—C5A | 121.75 (13) | N7B—C6B—C5B | 121.16 (12) |
N8A—N7A—C6A | 115.85 (12) | N8B—N7B—C6B | 115.40 (11) |
N8A—N7A—C7A | 122.26 (13) | N8B—N7B—C7B | 121.53 (11) |
C6A—N7A—C7A | 121.88 (13) | C6B—N7B—C7B | 122.86 (11) |
N7A—C7A—H7A | 109.5 | N7B—C7B—H7D | 109.5 |
N7A—C7A—H7B | 109.5 | N7B—C7B—H7E | 109.5 |
H7A—C7A—H7B | 109.5 | H7D—C7B—H7E | 109.5 |
N7A—C7A—H7C | 109.5 | N7B—C7B—H7F | 109.5 |
H7A—C7A—H7C | 109.5 | H7D—C7B—H7F | 109.5 |
H7B—C7A—H7C | 109.5 | H7E—C7B—H7F | 109.5 |
C9A—N8A—N7A | 120.21 (13) | C9B—N8B—N7B | 120.61 (12) |
N8A—C9A—C10A | 119.50 (13) | N8B—C9B—C10B | 118.40 (12) |
N8A—C9A—H9A | 120.3 | N8B—C9B—H9B | 120.8 |
C10A—C9A—H9A | 120.3 | C10B—C9B—H9B | 120.8 |
C14A—C10A—N11A | 105.08 (12) | C14B—C10B—N11B | 105.10 (12) |
C14A—C10A—C9A | 131.16 (14) | C14B—C10B—C9B | 131.69 (13) |
N11A—C10A—C9A | 123.74 (12) | N11B—C10B—C9B | 123.21 (12) |
C12A—N11A—C10A | 107.22 (12) | C12B—N11B—C10B | 107.29 (12) |
C12A—N11A—H11A | 124.4 (10) | C12B—N11B—H11B | 124.1 (10) |
C10A—N11A—H11A | 128.4 (10) | C10B—N11B—H11B | 128.6 (10) |
N13A—C12A—N11A | 112.61 (13) | N13B—C12B—N11B | 112.23 (13) |
N13A—C12A—H12A | 123.7 | N13B—C12B—H12B | 123.9 |
N11A—C12A—H12A | 123.7 | N11B—C12B—H12B | 123.9 |
C12A—N13A—C14A | 104.20 (12) | C12B—N13B—C14B | 104.56 (12) |
C10A—C14A—N13A | 110.88 (13) | C10B—C14B—N13B | 110.82 (13) |
C10A—C14A—H14A | 124.6 | C10B—C14B—H14B | 124.6 |
N13A—C14A—H14A | 124.6 | N13B—C14B—H14B | 124.6 |
C12H12N6·H2O | F(000) = 1088 |
Mr = 258.29 | Dx = 1.341 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2711 (7) Å | Cell parameters from 1351 reflections |
b = 14.0773 (12) Å | θ = 3.8–22.0° |
c = 22.2655 (16) Å | µ = 0.09 mm−1 |
β = 99.373 (8)° | T = 295 K |
V = 2557.9 (4) Å3 | Block, colourless |
Z = 8 | 0.25 × 0.2 × 0.2 mm |
Rigaku Xcalibur Eos diffractometer | 4502 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 2671 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
Detector resolution: 16.2413 pixels mm-1 | θmax = 25.0°, θmin = 2.9° |
ω scans | h = −9→8 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −16→14 |
Tmin = 0.987, Tmax = 1.000 | l = −26→24 |
9720 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.0345P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.95 | (Δ/σ)max < 0.001 |
4502 reflections | Δρmax = 0.14 e Å−3 |
377 parameters | Δρmin = −0.17 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.8016 (2) | 0.55051 (14) | 0.51023 (9) | 0.0557 (5) | |
C2A | 0.7451 (3) | 0.49279 (18) | 0.54771 (10) | 0.0498 (6) | |
N3A | 0.6744 (2) | 0.41254 (15) | 0.52159 (9) | 0.0546 (5) | |
H3A | 0.620 (3) | 0.3708 (19) | 0.5396 (11) | 0.084 (10)* | |
C4A | 0.6854 (3) | 0.41917 (18) | 0.46037 (10) | 0.0516 (6) | |
C5A | 0.6353 (3) | 0.35981 (19) | 0.41178 (11) | 0.0649 (7) | |
H5A | 0.5818 | 0.3029 | 0.4167 | 0.078* | |
C6A | 0.6672 (3) | 0.3877 (2) | 0.35545 (11) | 0.0751 (8) | |
H6A | 0.6358 | 0.3490 | 0.3217 | 0.090* | |
C7A | 0.7455 (3) | 0.4729 (3) | 0.34887 (12) | 0.0775 (9) | |
H7A | 0.7649 | 0.4904 | 0.3104 | 0.093* | |
C8A | 0.7960 (3) | 0.5330 (2) | 0.39729 (12) | 0.0701 (8) | |
H8A | 0.8487 | 0.5900 | 0.3921 | 0.084* | |
C9A | 0.7647 (3) | 0.50469 (19) | 0.45402 (10) | 0.0537 (6) | |
N10A | 0.7565 (2) | 0.50712 (15) | 0.60928 (8) | 0.0555 (5) | |
C10A | 0.8294 (3) | 0.59270 (18) | 0.63762 (11) | 0.0709 (8) | |
H10A | 0.8902 | 0.6243 | 0.6103 | 0.106* | |
H10B | 0.9017 | 0.5766 | 0.6744 | 0.106* | |
H10C | 0.7446 | 0.6341 | 0.6470 | 0.106* | |
N11A | 0.6686 (2) | 0.44424 (13) | 0.63728 (8) | 0.0511 (5) | |
C12A | 0.6511 (2) | 0.45719 (17) | 0.69275 (10) | 0.0540 (6) | |
H12A | 0.7012 | 0.5082 | 0.7150 | 0.065* | |
C13A | 0.5519 (3) | 0.39091 (19) | 0.71978 (10) | 0.0515 (6) | |
N14A | 0.4845 (2) | 0.31230 (15) | 0.69140 (10) | 0.0599 (6) | |
H14A | 0.493 (3) | 0.2927 (19) | 0.6481 (11) | 0.096 (9)* | |
C15A | 0.3926 (3) | 0.2704 (2) | 0.72949 (12) | 0.0766 (8) | |
H15A | 0.3303 | 0.2154 | 0.7222 | 0.092* | |
C16A | 0.4108 (3) | 0.3254 (2) | 0.78018 (11) | 0.0734 (8) | |
H16A | 0.3623 | 0.3133 | 0.8143 | 0.088* | |
N17A | 0.5105 (2) | 0.40146 (16) | 0.77419 (8) | 0.0608 (6) | |
N1B | 0.37852 (18) | −0.06562 (13) | 0.43343 (7) | 0.0435 (5) | |
C2B | 0.2985 (2) | −0.00740 (16) | 0.46394 (9) | 0.0386 (5) | |
N3B | 0.2820 (2) | 0.08276 (14) | 0.44092 (8) | 0.0431 (5) | |
H3B | 0.239 (3) | 0.1329 (17) | 0.4589 (10) | 0.082 (9)* | |
C4B | 0.3597 (2) | 0.08246 (17) | 0.39025 (9) | 0.0414 (5) | |
C5B | 0.3825 (3) | 0.15232 (18) | 0.34914 (9) | 0.0540 (6) | |
H5B | 0.3406 | 0.2132 | 0.3519 | 0.065* | |
C6B | 0.4701 (3) | 0.1283 (2) | 0.30377 (10) | 0.0634 (7) | |
H6B | 0.4892 | 0.1740 | 0.2756 | 0.076* | |
C7B | 0.5302 (3) | 0.0370 (2) | 0.29952 (10) | 0.0656 (8) | |
H7B | 0.5890 | 0.0227 | 0.2685 | 0.079* | |
C8B | 0.5050 (2) | −0.03307 (19) | 0.34020 (10) | 0.0571 (7) | |
H8B | 0.5451 | −0.0942 | 0.3368 | 0.068* | |
C9B | 0.4183 (2) | −0.00962 (17) | 0.38616 (9) | 0.0425 (5) | |
N10B | 0.23477 (18) | −0.03130 (13) | 0.51470 (7) | 0.0428 (4) | |
C10B | 0.2359 (3) | −0.12909 (15) | 0.53573 (9) | 0.0508 (6) | |
H10D | 0.2869 | −0.1688 | 0.5092 | 0.076* | |
H10E | 0.1253 | −0.1500 | 0.5356 | 0.076* | |
H10F | 0.2961 | −0.1330 | 0.5763 | 0.076* | |
N11B | 0.16643 (18) | 0.04169 (13) | 0.54156 (7) | 0.0424 (5) | |
C12B | 0.1063 (2) | 0.02586 (16) | 0.59005 (9) | 0.0434 (5) | |
H12B | 0.1101 | −0.0348 | 0.6067 | 0.052* | |
C13B | 0.0330 (2) | 0.10253 (17) | 0.61852 (9) | 0.0429 (6) | |
N14B | −0.0372 (2) | 0.08652 (17) | 0.66841 (8) | 0.0498 (5) | |
H14B | −0.040 (3) | 0.022 (2) | 0.6875 (11) | 0.106 (10)* | |
C15B | −0.1010 (3) | 0.1710 (2) | 0.68290 (10) | 0.0595 (7) | |
H15B | −0.1576 | 0.1824 | 0.7150 | 0.071* | |
C16B | −0.0661 (3) | 0.23489 (18) | 0.64171 (10) | 0.0595 (7) | |
H16B | −0.0954 | 0.2987 | 0.6410 | 0.071* | |
N17B | 0.0186 (2) | 0.19240 (14) | 0.60106 (8) | 0.0516 (5) | |
O1W | 0.5012 (3) | 0.25241 (13) | 0.56776 (8) | 0.0585 (5) | |
H1W1 | 0.553 (4) | 0.189 (3) | 0.5662 (14) | 0.172 (16)* | |
H1W2 | 0.405 (3) | 0.252 (2) | 0.5505 (13) | 0.107 (13)* | |
O2W | 0.1769 (2) | 0.25006 (14) | 0.50022 (8) | 0.0627 (5) | |
H2W1 | 0.168 (3) | 0.317 (3) | 0.4924 (13) | 0.130 (13)* | |
H2W2 | 0.118 (3) | 0.233 (2) | 0.5328 (14) | 0.138 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0576 (12) | 0.0437 (14) | 0.0681 (14) | 0.0025 (10) | 0.0172 (11) | 0.0103 (11) |
C2A | 0.0549 (14) | 0.0365 (16) | 0.0594 (15) | 0.0043 (12) | 0.0136 (12) | 0.0023 (13) |
N3A | 0.0755 (14) | 0.0383 (14) | 0.0515 (13) | −0.0017 (11) | 0.0146 (11) | 0.0059 (11) |
C4A | 0.0616 (14) | 0.0452 (17) | 0.0485 (15) | 0.0130 (13) | 0.0109 (12) | 0.0087 (13) |
C5A | 0.0802 (17) | 0.0561 (19) | 0.0566 (16) | 0.0104 (14) | 0.0055 (14) | 0.0040 (15) |
C6A | 0.0832 (19) | 0.089 (3) | 0.0520 (17) | 0.0272 (18) | 0.0091 (14) | 0.0015 (16) |
C7A | 0.0688 (18) | 0.106 (3) | 0.0610 (18) | 0.0223 (18) | 0.0217 (15) | 0.022 (2) |
C8A | 0.0605 (16) | 0.078 (2) | 0.0752 (18) | 0.0080 (14) | 0.0204 (15) | 0.0220 (18) |
C9A | 0.0515 (13) | 0.0547 (18) | 0.0579 (16) | 0.0117 (13) | 0.0177 (12) | 0.0144 (14) |
N10A | 0.0697 (12) | 0.0419 (14) | 0.0564 (12) | −0.0050 (11) | 0.0145 (10) | −0.0026 (11) |
C10A | 0.0758 (17) | 0.0509 (19) | 0.0847 (19) | −0.0077 (14) | 0.0087 (14) | −0.0133 (15) |
N11A | 0.0601 (12) | 0.0417 (13) | 0.0527 (12) | 0.0042 (10) | 0.0134 (10) | 0.0007 (10) |
C12A | 0.0555 (14) | 0.0502 (17) | 0.0557 (15) | 0.0079 (12) | 0.0071 (12) | −0.0090 (13) |
C13A | 0.0570 (14) | 0.0479 (17) | 0.0506 (15) | 0.0087 (13) | 0.0115 (12) | −0.0034 (13) |
N14A | 0.0787 (14) | 0.0479 (15) | 0.0580 (13) | 0.0031 (12) | 0.0251 (12) | −0.0074 (12) |
C15A | 0.100 (2) | 0.061 (2) | 0.0788 (19) | −0.0112 (16) | 0.0441 (17) | −0.0135 (16) |
C16A | 0.0907 (19) | 0.070 (2) | 0.0686 (18) | 0.0028 (17) | 0.0392 (16) | −0.0031 (17) |
N17A | 0.0697 (13) | 0.0662 (17) | 0.0497 (12) | 0.0062 (12) | 0.0192 (10) | −0.0082 (11) |
N1B | 0.0479 (10) | 0.0380 (12) | 0.0460 (11) | 0.0014 (9) | 0.0124 (9) | −0.0044 (9) |
C2B | 0.0391 (11) | 0.0370 (15) | 0.0396 (12) | −0.0006 (11) | 0.0059 (10) | −0.0031 (11) |
N3B | 0.0504 (11) | 0.0348 (13) | 0.0454 (11) | 0.0032 (10) | 0.0120 (9) | −0.0002 (10) |
C4B | 0.0444 (12) | 0.0433 (15) | 0.0370 (12) | −0.0044 (11) | 0.0082 (10) | −0.0008 (11) |
C5B | 0.0638 (14) | 0.0488 (17) | 0.0494 (14) | −0.0037 (12) | 0.0092 (12) | 0.0058 (13) |
C6B | 0.0718 (16) | 0.071 (2) | 0.0480 (15) | −0.0102 (15) | 0.0129 (13) | 0.0096 (14) |
C7B | 0.0724 (16) | 0.082 (2) | 0.0472 (15) | −0.0089 (16) | 0.0231 (13) | −0.0077 (16) |
C8B | 0.0616 (14) | 0.0564 (18) | 0.0569 (14) | −0.0010 (13) | 0.0205 (12) | −0.0128 (14) |
C9B | 0.0440 (12) | 0.0406 (15) | 0.0427 (12) | −0.0037 (11) | 0.0064 (10) | −0.0068 (12) |
N10B | 0.0522 (10) | 0.0349 (12) | 0.0437 (10) | 0.0039 (9) | 0.0158 (9) | 0.0015 (9) |
C10B | 0.0646 (14) | 0.0339 (15) | 0.0555 (14) | 0.0020 (12) | 0.0148 (12) | 0.0065 (12) |
N11B | 0.0478 (10) | 0.0392 (12) | 0.0416 (10) | 0.0036 (9) | 0.0112 (9) | −0.0015 (9) |
C12B | 0.0482 (12) | 0.0408 (15) | 0.0416 (12) | 0.0000 (11) | 0.0080 (10) | 0.0035 (11) |
C13B | 0.0467 (12) | 0.0460 (16) | 0.0373 (12) | −0.0014 (12) | 0.0112 (10) | −0.0022 (12) |
N14B | 0.0576 (11) | 0.0520 (15) | 0.0424 (11) | 0.0004 (11) | 0.0162 (9) | −0.0026 (11) |
C15B | 0.0691 (15) | 0.064 (2) | 0.0509 (15) | −0.0029 (14) | 0.0246 (13) | −0.0120 (14) |
C16B | 0.0711 (16) | 0.0467 (17) | 0.0637 (16) | 0.0043 (13) | 0.0203 (14) | −0.0062 (14) |
N17B | 0.0625 (11) | 0.0422 (13) | 0.0533 (12) | 0.0011 (10) | 0.0190 (10) | 0.0005 (10) |
O1W | 0.0702 (13) | 0.0425 (12) | 0.0637 (11) | 0.0022 (10) | 0.0136 (10) | −0.0049 (9) |
O2W | 0.0830 (11) | 0.0410 (12) | 0.0703 (12) | 0.0000 (10) | 0.0306 (10) | 0.0030 (10) |
N1A—C2A | 1.304 (3) | C2B—N10B | 1.365 (2) |
N1A—C9A | 1.397 (3) | C2B—N3B | 1.367 (3) |
C2A—N3A | 1.359 (3) | N3B—C4B | 1.386 (2) |
C2A—N10A | 1.374 (3) | N3B—H3B | 0.91 (2) |
N3A—C4A | 1.384 (3) | C4B—C5B | 1.377 (3) |
N3A—H3A | 0.88 (2) | C4B—C9B | 1.392 (3) |
C4A—C5A | 1.376 (3) | C5B—C6B | 1.377 (3) |
C4A—C9A | 1.389 (3) | C5B—H5B | 0.9300 |
C5A—C6A | 1.380 (3) | C6B—C7B | 1.388 (3) |
C5A—H5A | 0.9300 | C6B—H6B | 0.9300 |
C6A—C7A | 1.381 (4) | C7B—C8B | 1.377 (3) |
C6A—H6A | 0.9300 | C7B—H7B | 0.9300 |
C7A—C8A | 1.381 (4) | C8B—C9B | 1.382 (3) |
C7A—H7A | 0.9300 | C8B—H8B | 0.9300 |
C8A—C9A | 1.388 (3) | N10B—N11B | 1.357 (2) |
C8A—H8A | 0.9300 | N10B—C10B | 1.454 (2) |
N10A—N11A | 1.360 (2) | C10B—H10D | 0.9600 |
N10A—C10A | 1.445 (3) | C10B—H10E | 0.9600 |
C10A—H10A | 0.9600 | C10B—H10F | 0.9600 |
C10A—H10B | 0.9600 | N11B—C12B | 1.280 (2) |
C10A—H10C | 0.9600 | C12B—C13B | 1.435 (3) |
N11A—C12A | 1.280 (2) | C12B—H12B | 0.9300 |
C12A—C13A | 1.438 (3) | C13B—N17B | 1.323 (3) |
C12A—H12A | 0.9300 | C13B—N14B | 1.354 (2) |
C13A—N17A | 1.320 (2) | N14B—C15B | 1.360 (3) |
C13A—N14A | 1.349 (3) | N14B—H14B | 1.00 (3) |
N14A—C15A | 1.362 (3) | C15B—C16B | 1.349 (3) |
N14A—H14A | 1.02 (2) | C15B—H15B | 0.9300 |
C15A—C16A | 1.357 (3) | C16B—N17B | 1.369 (2) |
C15A—H15A | 0.9300 | C16B—H16B | 0.9300 |
C16A—N17A | 1.371 (3) | O1W—H1W1 | 1.00 (4) |
C16A—H16A | 0.9300 | O1W—H1W2 | 0.82 (3) |
N1B—C2B | 1.311 (2) | O2W—H2W1 | 0.96 (4) |
N1B—C9B | 1.396 (2) | O2W—H2W2 | 0.97 (3) |
C2A—N1A—C9A | 103.7 (2) | N1B—C2B—N10B | 124.8 (2) |
N1A—C2A—N3A | 114.7 (2) | N1B—C2B—N3B | 114.47 (18) |
N1A—C2A—N10A | 125.0 (2) | N10B—C2B—N3B | 120.72 (19) |
N3A—C2A—N10A | 120.3 (2) | C2B—N3B—C4B | 105.72 (19) |
C2A—N3A—C4A | 105.8 (2) | C2B—N3B—H3B | 125.2 (14) |
C2A—N3A—H3A | 125.4 (16) | C4B—N3B—H3B | 128.6 (14) |
C4A—N3A—H3A | 128.1 (17) | C5B—C4B—N3B | 132.1 (2) |
C5A—C4A—N3A | 132.3 (2) | C5B—C4B—C9B | 122.3 (2) |
C5A—C4A—C9A | 122.2 (2) | N3B—C4B—C9B | 105.57 (19) |
N3A—C4A—C9A | 105.5 (2) | C4B—C5B—C6B | 117.2 (2) |
C4A—C5A—C6A | 117.6 (3) | C4B—C5B—H5B | 121.4 |
C4A—C5A—H5A | 121.2 | C6B—C5B—H5B | 121.4 |
C6A—C5A—H5A | 121.2 | C5B—C6B—C7B | 120.9 (2) |
C5A—C6A—C7A | 120.4 (3) | C5B—C6B—H6B | 119.5 |
C5A—C6A—H6A | 119.8 | C7B—C6B—H6B | 119.5 |
C7A—C6A—H6A | 119.8 | C8B—C7B—C6B | 121.6 (2) |
C8A—C7A—C6A | 122.5 (3) | C8B—C7B—H7B | 119.2 |
C8A—C7A—H7A | 118.8 | C6B—C7B—H7B | 119.2 |
C6A—C7A—H7A | 118.8 | C7B—C8B—C9B | 117.9 (2) |
C7A—C8A—C9A | 117.2 (3) | C7B—C8B—H8B | 121.0 |
C7A—C8A—H8A | 121.4 | C9B—C8B—H8B | 121.0 |
C9A—C8A—H8A | 121.4 | C8B—C9B—C4B | 119.9 (2) |
C8A—C9A—C4A | 120.1 (3) | C8B—C9B—N1B | 129.6 (2) |
C8A—C9A—N1A | 129.6 (3) | C4B—C9B—N1B | 110.45 (18) |
C4A—C9A—N1A | 110.30 (19) | N11B—N10B—C2B | 115.02 (18) |
N11A—N10A—C2A | 114.03 (19) | N11B—N10B—C10B | 123.78 (16) |
N11A—N10A—C10A | 123.95 (18) | C2B—N10B—C10B | 121.15 (18) |
C2A—N10A—C10A | 120.9 (2) | N10B—C10B—H10D | 109.5 |
N10A—C10A—H10A | 109.5 | N10B—C10B—H10E | 109.5 |
N10A—C10A—H10B | 109.5 | H10D—C10B—H10E | 109.5 |
H10A—C10A—H10B | 109.5 | N10B—C10B—H10F | 109.5 |
N10A—C10A—H10C | 109.5 | H10D—C10B—H10F | 109.5 |
H10A—C10A—H10C | 109.5 | H10E—C10B—H10F | 109.5 |
H10B—C10A—H10C | 109.5 | C12B—N11B—N10B | 119.13 (18) |
C12A—N11A—N10A | 120.2 (2) | N11B—C12B—C13B | 119.5 (2) |
N11A—C12A—C13A | 118.3 (2) | N11B—C12B—H12B | 120.3 |
N11A—C12A—H12A | 120.9 | C13B—C12B—H12B | 120.3 |
C13A—C12A—H12A | 120.9 | N17B—C13B—N14B | 111.7 (2) |
N17A—C13A—N14A | 111.9 (2) | N17B—C13B—C12B | 127.85 (19) |
N17A—C13A—C12A | 124.2 (2) | N14B—C13B—C12B | 120.4 (2) |
N14A—C13A—C12A | 123.8 (2) | C13B—N14B—C15B | 106.5 (2) |
C13A—N14A—C15A | 107.1 (2) | C13B—N14B—H14B | 122.7 (14) |
C13A—N14A—H14A | 125.4 (15) | C15B—N14B—H14B | 130.8 (14) |
C15A—N14A—H14A | 127.2 (14) | C16B—C15B—N14B | 106.7 (2) |
C16A—C15A—N14A | 105.9 (2) | C16B—C15B—H15B | 126.6 |
C16A—C15A—H15A | 127.1 | N14B—C15B—H15B | 126.6 |
N14A—C15A—H15A | 127.1 | C15B—C16B—N17B | 110.3 (2) |
C15A—C16A—N17A | 110.6 (2) | C15B—C16B—H16B | 124.8 |
C15A—C16A—H16A | 124.7 | N17B—C16B—H16B | 124.8 |
N17A—C16A—H16A | 124.7 | C13B—N17B—C16B | 104.75 (19) |
C13A—N17A—C16A | 104.6 (2) | H1W1—O1W—H1W2 | 111 (3) |
C2B—N1B—C9B | 103.79 (18) | H2W1—O2W—H2W2 | 111 (2) |
C9A—N1A—C2A—N3A | 0.2 (3) | C9B—N1B—C2B—N10B | 179.95 (17) |
C9A—N1A—C2A—N10A | 178.6 (2) | C9B—N1B—C2B—N3B | −0.1 (2) |
N1A—C2A—N3A—C4A | −0.3 (3) | N1B—C2B—N3B—C4B | 0.0 (2) |
N10A—C2A—N3A—C4A | −178.80 (19) | N10B—C2B—N3B—C4B | 179.92 (16) |
C2A—N3A—C4A—C5A | −179.9 (2) | C2B—N3B—C4B—C5B | −180.0 (2) |
C2A—N3A—C4A—C9A | 0.3 (2) | C2B—N3B—C4B—C9B | 0.2 (2) |
N3A—C4A—C5A—C6A | −179.4 (2) | N3B—C4B—C5B—C6B | 178.7 (2) |
C9A—C4A—C5A—C6A | 0.4 (3) | C9B—C4B—C5B—C6B | −1.5 (3) |
C4A—C5A—C6A—C7A | −0.6 (3) | C4B—C5B—C6B—C7B | 0.9 (3) |
C5A—C6A—C7A—C8A | 0.5 (4) | C5B—C6B—C7B—C8B | 0.0 (4) |
C6A—C7A—C8A—C9A | −0.1 (4) | C6B—C7B—C8B—C9B | −0.5 (3) |
C7A—C8A—C9A—C4A | −0.1 (3) | C7B—C8B—C9B—C4B | −0.1 (3) |
C7A—C8A—C9A—N1A | 179.9 (2) | C7B—C8B—C9B—N1B | −178.65 (19) |
C5A—C4A—C9A—C8A | 0.0 (3) | C5B—C4B—C9B—C8B | 1.1 (3) |
N3A—C4A—C9A—C8A | 179.79 (19) | N3B—C4B—C9B—C8B | −179.06 (17) |
C5A—C4A—C9A—N1A | 180.0 (2) | C5B—C4B—C9B—N1B | 179.90 (18) |
N3A—C4A—C9A—N1A | −0.2 (2) | N3B—C4B—C9B—N1B | −0.2 (2) |
C2A—N1A—C9A—C8A | −180.0 (2) | C2B—N1B—C9B—C8B | 178.9 (2) |
C2A—N1A—C9A—C4A | 0.1 (2) | C2B—N1B—C9B—C4B | 0.2 (2) |
N1A—C2A—N10A—N11A | 171.11 (19) | N1B—C2B—N10B—N11B | 175.63 (17) |
N3A—C2A—N10A—N11A | −10.6 (3) | N3B—C2B—N10B—N11B | −4.3 (2) |
N1A—C2A—N10A—C10A | 2.5 (3) | N1B—C2B—N10B—C10B | −6.8 (3) |
N3A—C2A—N10A—C10A | −179.1 (2) | N3B—C2B—N10B—C10B | 173.23 (18) |
C2A—N10A—N11A—C12A | −170.73 (19) | C2B—N10B—N11B—C12B | −178.78 (17) |
C10A—N10A—N11A—C12A | −2.6 (3) | C10B—N10B—N11B—C12B | 3.7 (3) |
N10A—N11A—C12A—C13A | 177.65 (18) | N10B—N11B—C12B—C13B | −179.63 (16) |
N11A—C12A—C13A—N17A | −172.8 (2) | N11B—C12B—C13B—N17B | −0.5 (3) |
N11A—C12A—C13A—N14A | 4.4 (3) | N11B—C12B—C13B—N14B | 177.31 (18) |
N17A—C13A—N14A—C15A | 0.8 (3) | N17B—C13B—N14B—C15B | 0.6 (2) |
C12A—C13A—N14A—C15A | −176.7 (2) | C12B—C13B—N14B—C15B | −177.46 (18) |
C13A—N14A—C15A—C16A | −0.9 (3) | C13B—N14B—C15B—C16B | −0.5 (2) |
N14A—C15A—C16A—N17A | 0.7 (3) | N14B—C15B—C16B—N17B | 0.2 (3) |
N14A—C13A—N17A—C16A | −0.3 (3) | N14B—C13B—N17B—C16B | −0.5 (2) |
C12A—C13A—N17A—C16A | 177.2 (2) | C12B—C13B—N17B—C16B | 177.40 (19) |
C15A—C16A—N17A—C13A | −0.3 (3) | C15B—C16B—N17B—C13B | 0.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3A—H3A···O1W | 0.88 (2) | 2.08 (2) | 2.944 (3) | 168 (2) |
N14A—H14A···O1W | 1.02 (2) | 1.89 (2) | 2.904 (3) | 177 (2) |
N3B—H3B···O2W | 0.91 (2) | 2.00 (2) | 2.902 (3) | 172 (2) |
N14B—H14B···N17Ai | 1.00 (3) | 1.90 (3) | 2.894 (3) | 172 (2) |
O1W—H1W1···N1Bii | 1.00 (4) | 1.82 (4) | 2.813 (3) | 172 (3) |
O1W—H1W2···O2W | 0.82 (3) | 2.03 (3) | 2.854 (3) | 175 (3) |
O2W—H2W1···N1Aiii | 0.96 (4) | 1.88 (4) | 2.825 (3) | 167 (3) |
O2W—H2W2···N17B | 0.97 (3) | 1.93 (3) | 2.893 (2) | 175 (3) |
Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+1. |
4C13H14N6·5H2O | Z = 2 |
Mr = 1107.28 | F(000) = 1172 |
Triclinic, P1 | Dx = 1.277 Mg m−3 |
a = 9.1836 (3) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 16.5814 (4) Å | Cell parameters from 24014 reflections |
c = 20.8041 (6) Å | θ = 2.9–75.9° |
α = 106.760 (2)° | µ = 0.72 mm−1 |
β = 97.854 (2)° | T = 130 K |
γ = 103.408 (2)° | Plate, yellow |
V = 2879.43 (15) Å3 | 0.25 × 0.25 × 0.08 mm |
Rigaku SuperNova diffractometer with an Atlas detector | 11893 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 9917 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.039 |
ω scans | θmax = 77.2°, θmin = 2.3° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2019) | h = −11→11 |
Tmin = 0.702, Tmax = 1.000 | k = −20→20 |
51173 measured reflections | l = −26→26 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.047 | w = 1/[σ2(Fo2) + (0.0801P)2 + 0.6386P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.140 | (Δ/σ)max = 0.001 |
S = 1.02 | Δρmax = 0.37 e Å−3 |
11893 reflections | Δρmin = −0.27 e Å−3 |
739 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.00062 (11) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.1006 (2) | 0.65283 (9) | 0.30680 (7) | 0.0529 (4) | |
C2A | 0.2002 (2) | 0.70535 (10) | 0.36361 (8) | 0.0439 (4) | |
N3A | 0.31496 (17) | 0.67284 (8) | 0.38354 (8) | 0.0476 (3) | |
H3A | 0.3911 | 0.6988 | 0.4199 | 0.057* | |
C4A | 0.2878 (2) | 0.59034 (10) | 0.33486 (10) | 0.0527 (5) | |
C5A | 0.3646 (3) | 0.52657 (11) | 0.32779 (13) | 0.0681 (6) | |
H5A | 0.4545 | 0.5343 | 0.3603 | 0.082* | |
C6A | 0.3036 (3) | 0.45072 (12) | 0.27088 (15) | 0.0802 (8) | |
H6A | 0.3537 | 0.4058 | 0.2641 | 0.096* | |
C7A | 0.1718 (4) | 0.43884 (13) | 0.22374 (13) | 0.0802 (8) | |
H7A | 0.1339 | 0.3859 | 0.1856 | 0.096* | |
C8A | 0.0938 (3) | 0.50202 (12) | 0.23071 (10) | 0.0696 (6) | |
H8A | 0.0032 | 0.4935 | 0.1983 | 0.084* | |
C9A | 0.1543 (3) | 0.57897 (11) | 0.28765 (9) | 0.0557 (5) | |
N10A | 0.19294 (16) | 0.78744 (8) | 0.39994 (7) | 0.0433 (3) | |
C10A | 0.0724 (2) | 0.82248 (11) | 0.37705 (9) | 0.0489 (4) | |
H10A | 0.0169 | 0.8378 | 0.4137 | 0.073* | |
H10B | 0.0012 | 0.7782 | 0.3360 | 0.073* | |
H10C | 0.1178 | 0.8751 | 0.3660 | 0.073* | |
N11A | 0.30574 (15) | 0.83167 (8) | 0.45715 (7) | 0.0405 (3) | |
C12A | 0.30878 (17) | 0.90948 (9) | 0.49366 (8) | 0.0392 (3) | |
H12A | 0.2353 | 0.9367 | 0.4800 | 0.047* | |
C13A | 0.42641 (17) | 0.95447 (9) | 0.55576 (8) | 0.0388 (3) | |
N14A | 0.43848 (15) | 1.03703 (8) | 0.59762 (7) | 0.0390 (3) | |
C14A | 0.3458 (2) | 1.09420 (10) | 0.58572 (9) | 0.0445 (4) | |
H14A | 0.3602 | 1.1071 | 0.5435 | 0.067* | |
H14B | 0.3776 | 1.1492 | 0.6247 | 0.067* | |
H14C | 0.2373 | 1.0646 | 0.5809 | 0.067* | |
C15A | 0.55619 (18) | 1.05772 (10) | 0.65305 (8) | 0.0424 (3) | |
H15A | 0.5916 | 1.1107 | 0.6912 | 0.051* | |
C16A | 0.61218 (19) | 0.98671 (10) | 0.64232 (9) | 0.0442 (3) | |
H16A | 0.6952 | 0.9825 | 0.6726 | 0.053* | |
N17A | 0.53181 (15) | 0.92211 (8) | 0.58154 (7) | 0.0426 (3) | |
N1B | −0.12074 (14) | 0.77801 (8) | 0.50452 (7) | 0.0394 (3) | |
C2B | −0.03609 (17) | 0.72259 (10) | 0.49817 (8) | 0.0377 (3) | |
N3B | 0.09466 (14) | 0.75019 (8) | 0.54767 (6) | 0.0368 (3) | |
H3B | 0.1639 | 0.7220 | 0.5513 | 0.044* | |
C4B | 0.09702 (16) | 0.83176 (9) | 0.59129 (8) | 0.0350 (3) | |
C5B | 0.19983 (17) | 0.89038 (10) | 0.65015 (8) | 0.0390 (3) | |
H5B | 0.2907 | 0.8787 | 0.6680 | 0.047* | |
C6B | 0.16441 (17) | 0.96739 (10) | 0.68222 (8) | 0.0399 (3) | |
H6B | 0.2323 | 1.0091 | 0.7229 | 0.048* | |
C7B | 0.03097 (18) | 0.98443 (10) | 0.65567 (8) | 0.0402 (3) | |
H7B | 0.0095 | 1.0373 | 0.6789 | 0.048* | |
C8B | −0.07084 (17) | 0.92560 (10) | 0.59604 (8) | 0.0397 (3) | |
H8B | −0.1607 | 0.9379 | 0.5778 | 0.048* | |
C9B | −0.03759 (16) | 0.84811 (9) | 0.56367 (8) | 0.0367 (3) | |
N10B | −0.07246 (15) | 0.64388 (8) | 0.44646 (7) | 0.0423 (3) | |
C10B | −0.2115 (2) | 0.61264 (12) | 0.39344 (10) | 0.0536 (4) | |
H10D | −0.1855 | 0.5991 | 0.3481 | 0.080* | |
H10E | −0.2648 | 0.6582 | 0.3991 | 0.080* | |
H10F | −0.2783 | 0.5595 | 0.3971 | 0.080* | |
N11B | 0.02528 (15) | 0.59472 (8) | 0.45275 (7) | 0.0409 (3) | |
C12B | −0.00486 (19) | 0.51711 (10) | 0.40921 (9) | 0.0432 (3) | |
H12B | −0.0940 | 0.4937 | 0.3731 | 0.052* | |
C13B | 0.10147 (18) | 0.46625 (10) | 0.41691 (9) | 0.0431 (4) | |
N14B | 0.07809 (16) | 0.38259 (8) | 0.37481 (7) | 0.0455 (3) | |
C14B | −0.0531 (2) | 0.33053 (11) | 0.31835 (9) | 0.0534 (4) | |
H14D | −0.1476 | 0.3261 | 0.3357 | 0.080* | |
H14E | −0.0425 | 0.2716 | 0.2982 | 0.080* | |
H14F | −0.0575 | 0.3590 | 0.2831 | 0.080* | |
C15B | 0.2000 (2) | 0.35555 (11) | 0.39614 (10) | 0.0513 (4) | |
H15B | 0.2165 | 0.3000 | 0.3767 | 0.062* | |
C16B | 0.2936 (2) | 0.42408 (11) | 0.45094 (10) | 0.0520 (4) | |
H16B | 0.3876 | 0.4238 | 0.4763 | 0.062* | |
N17B | 0.23158 (16) | 0.49358 (9) | 0.46407 (8) | 0.0478 (3) | |
N1C | 0.90144 (15) | 0.77482 (8) | 0.91446 (7) | 0.0429 (3) | |
C2C | 0.77356 (17) | 0.73583 (9) | 0.92967 (8) | 0.0392 (3) | |
N3C | 0.64301 (15) | 0.72889 (8) | 0.88699 (7) | 0.0422 (3) | |
H3C | 0.5486 | 0.7052 | 0.8895 | 0.051* | |
C4C | 0.68662 (19) | 0.76641 (9) | 0.83840 (9) | 0.0423 (3) | |
C5C | 0.6040 (2) | 0.77749 (11) | 0.78278 (10) | 0.0509 (4) | |
H5C | 0.4951 | 0.7593 | 0.7721 | 0.061* | |
C6C | 0.6872 (2) | 0.81654 (11) | 0.74279 (10) | 0.0563 (4) | |
H6C | 0.6339 | 0.8249 | 0.7039 | 0.068* | |
C7C | 0.8469 (2) | 0.84344 (11) | 0.75901 (10) | 0.0562 (5) | |
H7C | 0.9005 | 0.8697 | 0.7308 | 0.067* | |
C8C | 0.9292 (2) | 0.83277 (10) | 0.81533 (9) | 0.0507 (4) | |
H8C | 1.0382 | 0.8514 | 0.8261 | 0.061* | |
C9C | 0.84778 (19) | 0.79387 (9) | 0.85592 (8) | 0.0426 (3) | |
N10C | 0.77001 (15) | 0.70443 (8) | 0.98395 (7) | 0.0429 (3) | |
C10C | 0.90810 (19) | 0.71395 (11) | 1.03182 (9) | 0.0487 (4) | |
H10G | 0.9090 | 0.7529 | 1.0775 | 0.073* | |
H10H | 0.9981 | 0.7392 | 1.0160 | 0.073* | |
H10I | 0.9107 | 0.6562 | 1.0344 | 0.073* | |
N11C | 0.62613 (15) | 0.66466 (8) | 0.98822 (7) | 0.0424 (3) | |
C12C | 0.60595 (19) | 0.63293 (10) | 1.03705 (9) | 0.0438 (4) | |
H12C | 0.6889 | 0.6368 | 1.0716 | 0.053* | |
C13C | 0.4465 (2) | 0.59059 (10) | 1.03555 (9) | 0.0467 (4) | |
N14C | 0.40234 (17) | 0.55088 (9) | 1.08143 (8) | 0.0496 (3) | |
C14C | 0.4992 (2) | 0.53727 (12) | 1.13622 (10) | 0.0565 (5) | |
H14G | 0.5441 | 0.4901 | 1.1165 | 0.085* | |
H14H | 0.4375 | 0.5208 | 1.1678 | 0.085* | |
H14I | 0.5813 | 0.5916 | 1.1614 | 0.085* | |
C15C | 0.2457 (2) | 0.52005 (11) | 1.06339 (11) | 0.0570 (5) | |
H15C | 0.1807 | 0.4896 | 1.0859 | 0.068* | |
C16C | 0.2012 (2) | 0.54155 (12) | 1.00693 (11) | 0.0577 (5) | |
H16C | 0.0980 | 0.5279 | 0.9831 | 0.069* | |
N17C | 0.32713 (16) | 0.58581 (9) | 0.98952 (8) | 0.0508 (3) | |
N1D | 0.69809 (15) | 0.84644 (8) | 1.14451 (7) | 0.0399 (3) | |
C2D | 0.62430 (17) | 0.85759 (9) | 1.09017 (8) | 0.0370 (3) | |
N3D | 0.46901 (14) | 0.82471 (8) | 1.07649 (7) | 0.0382 (3) | |
H3D | 0.4022 | 0.8257 | 1.0423 | 0.046* | |
C4D | 0.43775 (19) | 0.78909 (9) | 1.12775 (8) | 0.0405 (3) | |
C5D | 0.3007 (2) | 0.74768 (10) | 1.14076 (9) | 0.0480 (4) | |
H5D | 0.2043 | 0.7397 | 1.1127 | 0.058* | |
C6D | 0.3122 (2) | 0.71870 (11) | 1.19686 (10) | 0.0535 (4) | |
H6D | 0.2212 | 0.6900 | 1.2076 | 0.064* | |
C7D | 0.4533 (2) | 0.73041 (11) | 1.23789 (9) | 0.0531 (4) | |
H7D | 0.4561 | 0.7089 | 1.2756 | 0.064* | |
C8D | 0.5903 (2) | 0.77276 (10) | 1.22529 (8) | 0.0477 (4) | |
H8D | 0.6864 | 0.7810 | 1.2538 | 0.057* | |
C9D | 0.58099 (19) | 0.80276 (10) | 1.16908 (8) | 0.0412 (3) | |
N10D | 0.69364 (14) | 0.89884 (8) | 1.04912 (6) | 0.0378 (3) | |
C10D | 0.85700 (17) | 0.94191 (11) | 1.06742 (8) | 0.0431 (3) | |
H10J | 0.9040 | 0.9174 | 1.0296 | 0.065* | |
H10K | 0.9028 | 0.9324 | 1.1090 | 0.065* | |
H10L | 0.8748 | 1.0051 | 1.0761 | 0.065* | |
N11D | 0.59626 (14) | 0.90323 (8) | 0.99588 (6) | 0.0362 (3) | |
C12D | 0.65110 (16) | 0.94564 (9) | 0.95770 (7) | 0.0357 (3) | |
H12D | 0.7577 | 0.9746 | 0.9672 | 0.043* | |
C13D | 0.54862 (16) | 0.94869 (9) | 0.90029 (7) | 0.0346 (3) | |
N14D | 0.59963 (13) | 0.99073 (7) | 0.85647 (6) | 0.0346 (2) | |
C14D | 0.75707 (17) | 1.03912 (10) | 0.86089 (9) | 0.0414 (3) | |
H14J | 0.7978 | 1.0841 | 0.9064 | 0.062* | |
H14K | 0.7590 | 1.0673 | 0.8255 | 0.062* | |
H14L | 0.8202 | 0.9984 | 0.8537 | 0.062* | |
C15D | 0.47602 (17) | 0.97874 (10) | 0.80676 (8) | 0.0390 (3) | |
H15D | 0.4755 | 1.0001 | 0.7690 | 0.047* | |
C16D | 0.35309 (18) | 0.92978 (11) | 0.82211 (8) | 0.0421 (3) | |
H16D | 0.2508 | 0.9112 | 0.7960 | 0.051* | |
N17D | 0.39775 (14) | 0.91102 (8) | 0.88071 (6) | 0.0385 (3) | |
O1W | 0.99057 (19) | 0.83613 (13) | 0.20951 (8) | 0.0822 (5) | |
H1WA | 0.9140 | 0.8453 | 0.1911 | 0.123* | |
H1WB | 0.9686 | 0.7696 | 0.2074 | 0.123* | |
O2W | 0.32669 (13) | 0.66353 (8) | 0.56699 (7) | 0.0546 (3) | |
H2WA | 0.4146 | 0.6897 | 0.5630 | 0.082* | |
H2WB | 0.2992 | 0.6084 | 0.5292 | 0.082* | |
O3W | 0.32990 (14) | 0.66653 (8) | 0.88886 (7) | 0.0541 (3) | |
H3WA | 0.2933 | 0.7092 | 0.9038 | 0.081* | |
H3WB | 0.3377 | 0.6452 | 0.9214 | 0.081* | |
O4W | 0.23582 (13) | 0.81835 (8) | 0.95918 (6) | 0.0492 (3) | |
H4WA | 0.2838 | 0.8587 | 0.9373 | 0.074* | |
H4WB | 0.1391 | 0.8096 | 0.9460 | 0.074* | |
O5W | 0.55630 (13) | 0.74966 (7) | 0.50868 (7) | 0.0528 (3) | |
H5WA | 0.6494 | 0.7521 | 0.5115 | 0.079* | |
H5WB | 0.5606 | 0.7994 | 0.5341 | 0.079* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0857 (11) | 0.0338 (7) | 0.0463 (8) | 0.0178 (7) | 0.0292 (7) | 0.0166 (6) |
C2A | 0.0623 (10) | 0.0308 (7) | 0.0482 (8) | 0.0151 (7) | 0.0314 (8) | 0.0169 (6) |
N3A | 0.0567 (8) | 0.0304 (6) | 0.0658 (9) | 0.0154 (6) | 0.0360 (7) | 0.0182 (6) |
C4A | 0.0728 (11) | 0.0304 (7) | 0.0678 (11) | 0.0162 (7) | 0.0478 (10) | 0.0194 (7) |
C5A | 0.0727 (12) | 0.0368 (9) | 0.1093 (17) | 0.0200 (8) | 0.0616 (13) | 0.0235 (10) |
C6A | 0.1079 (19) | 0.0349 (9) | 0.117 (2) | 0.0263 (11) | 0.0828 (18) | 0.0220 (11) |
C7A | 0.138 (2) | 0.0357 (9) | 0.0785 (15) | 0.0215 (12) | 0.0734 (17) | 0.0164 (9) |
C8A | 0.1266 (19) | 0.0381 (9) | 0.0511 (10) | 0.0200 (10) | 0.0447 (12) | 0.0165 (8) |
C9A | 0.0928 (14) | 0.0335 (8) | 0.0522 (10) | 0.0187 (8) | 0.0430 (10) | 0.0183 (7) |
N10A | 0.0543 (8) | 0.0304 (6) | 0.0493 (7) | 0.0144 (6) | 0.0208 (6) | 0.0132 (5) |
C10A | 0.0623 (10) | 0.0378 (8) | 0.0537 (9) | 0.0200 (7) | 0.0205 (8) | 0.0177 (7) |
N11A | 0.0474 (7) | 0.0321 (6) | 0.0490 (7) | 0.0131 (5) | 0.0246 (6) | 0.0161 (5) |
C12A | 0.0446 (8) | 0.0314 (7) | 0.0510 (8) | 0.0144 (6) | 0.0260 (7) | 0.0176 (6) |
C13A | 0.0452 (8) | 0.0312 (7) | 0.0500 (8) | 0.0147 (6) | 0.0281 (7) | 0.0172 (6) |
N14A | 0.0472 (7) | 0.0320 (6) | 0.0466 (7) | 0.0154 (5) | 0.0250 (6) | 0.0160 (5) |
C14A | 0.0563 (9) | 0.0339 (7) | 0.0512 (9) | 0.0200 (7) | 0.0234 (7) | 0.0150 (7) |
C15A | 0.0487 (8) | 0.0393 (8) | 0.0451 (8) | 0.0144 (7) | 0.0227 (7) | 0.0157 (6) |
C16A | 0.0481 (8) | 0.0436 (8) | 0.0491 (8) | 0.0170 (7) | 0.0238 (7) | 0.0182 (7) |
N17A | 0.0470 (7) | 0.0373 (6) | 0.0537 (8) | 0.0179 (6) | 0.0260 (6) | 0.0188 (6) |
N1B | 0.0380 (6) | 0.0386 (6) | 0.0448 (7) | 0.0147 (5) | 0.0145 (5) | 0.0130 (5) |
C2B | 0.0371 (7) | 0.0368 (7) | 0.0445 (8) | 0.0121 (6) | 0.0189 (6) | 0.0156 (6) |
N3B | 0.0345 (6) | 0.0359 (6) | 0.0467 (7) | 0.0142 (5) | 0.0171 (5) | 0.0171 (5) |
C4B | 0.0339 (7) | 0.0342 (7) | 0.0430 (7) | 0.0106 (5) | 0.0178 (6) | 0.0171 (6) |
C5B | 0.0361 (7) | 0.0404 (7) | 0.0471 (8) | 0.0118 (6) | 0.0163 (6) | 0.0204 (6) |
C6B | 0.0411 (8) | 0.0373 (7) | 0.0439 (8) | 0.0098 (6) | 0.0151 (6) | 0.0157 (6) |
C7B | 0.0447 (8) | 0.0350 (7) | 0.0468 (8) | 0.0151 (6) | 0.0180 (7) | 0.0159 (6) |
C8B | 0.0397 (7) | 0.0404 (8) | 0.0467 (8) | 0.0174 (6) | 0.0150 (6) | 0.0186 (6) |
C9B | 0.0361 (7) | 0.0358 (7) | 0.0437 (8) | 0.0115 (6) | 0.0162 (6) | 0.0170 (6) |
N10B | 0.0389 (6) | 0.0400 (7) | 0.0496 (7) | 0.0156 (5) | 0.0158 (6) | 0.0110 (6) |
C10B | 0.0473 (9) | 0.0523 (10) | 0.0553 (10) | 0.0194 (8) | 0.0095 (8) | 0.0058 (8) |
N11B | 0.0415 (7) | 0.0373 (6) | 0.0522 (7) | 0.0153 (5) | 0.0242 (6) | 0.0178 (6) |
C12B | 0.0443 (8) | 0.0390 (8) | 0.0513 (9) | 0.0128 (6) | 0.0248 (7) | 0.0148 (7) |
C13B | 0.0466 (8) | 0.0350 (7) | 0.0556 (9) | 0.0129 (6) | 0.0289 (7) | 0.0174 (7) |
N14B | 0.0519 (8) | 0.0362 (6) | 0.0560 (8) | 0.0143 (6) | 0.0292 (6) | 0.0172 (6) |
C14B | 0.0652 (11) | 0.0413 (8) | 0.0557 (10) | 0.0169 (8) | 0.0256 (9) | 0.0121 (7) |
C15B | 0.0597 (10) | 0.0385 (8) | 0.0695 (11) | 0.0212 (8) | 0.0333 (9) | 0.0241 (8) |
C16B | 0.0515 (9) | 0.0433 (9) | 0.0744 (12) | 0.0196 (7) | 0.0283 (9) | 0.0275 (8) |
N17B | 0.0467 (7) | 0.0388 (7) | 0.0657 (9) | 0.0142 (6) | 0.0262 (7) | 0.0211 (6) |
N1C | 0.0437 (7) | 0.0318 (6) | 0.0513 (7) | 0.0060 (5) | 0.0253 (6) | 0.0080 (5) |
C2C | 0.0421 (8) | 0.0282 (6) | 0.0487 (8) | 0.0101 (6) | 0.0235 (7) | 0.0085 (6) |
N3C | 0.0419 (7) | 0.0350 (6) | 0.0569 (8) | 0.0123 (5) | 0.0269 (6) | 0.0176 (6) |
C4C | 0.0497 (8) | 0.0296 (7) | 0.0545 (9) | 0.0154 (6) | 0.0283 (7) | 0.0134 (6) |
C5C | 0.0585 (10) | 0.0418 (8) | 0.0637 (10) | 0.0231 (8) | 0.0288 (9) | 0.0202 (8) |
C6C | 0.0801 (13) | 0.0415 (9) | 0.0617 (11) | 0.0271 (9) | 0.0353 (10) | 0.0218 (8) |
C7C | 0.0781 (12) | 0.0381 (8) | 0.0626 (11) | 0.0177 (8) | 0.0421 (10) | 0.0192 (8) |
C8C | 0.0581 (10) | 0.0336 (7) | 0.0591 (10) | 0.0060 (7) | 0.0336 (8) | 0.0097 (7) |
C9C | 0.0500 (8) | 0.0269 (6) | 0.0520 (9) | 0.0090 (6) | 0.0278 (7) | 0.0089 (6) |
N10C | 0.0409 (7) | 0.0378 (6) | 0.0537 (7) | 0.0088 (5) | 0.0235 (6) | 0.0165 (6) |
C10C | 0.0460 (9) | 0.0451 (9) | 0.0572 (10) | 0.0098 (7) | 0.0215 (8) | 0.0181 (7) |
N11C | 0.0428 (7) | 0.0318 (6) | 0.0579 (8) | 0.0108 (5) | 0.0278 (6) | 0.0147 (6) |
C12C | 0.0486 (8) | 0.0333 (7) | 0.0563 (9) | 0.0140 (6) | 0.0279 (7) | 0.0158 (7) |
C13C | 0.0530 (9) | 0.0334 (7) | 0.0633 (10) | 0.0149 (7) | 0.0349 (8) | 0.0181 (7) |
N14C | 0.0601 (9) | 0.0349 (6) | 0.0644 (9) | 0.0154 (6) | 0.0378 (7) | 0.0197 (6) |
C14C | 0.0726 (12) | 0.0430 (9) | 0.0648 (11) | 0.0184 (8) | 0.0378 (10) | 0.0222 (8) |
C15C | 0.0588 (10) | 0.0420 (9) | 0.0774 (12) | 0.0100 (8) | 0.0433 (10) | 0.0209 (8) |
C16C | 0.0489 (9) | 0.0494 (9) | 0.0805 (13) | 0.0090 (8) | 0.0366 (9) | 0.0238 (9) |
N17C | 0.0468 (8) | 0.0436 (7) | 0.0705 (9) | 0.0130 (6) | 0.0323 (7) | 0.0228 (7) |
N1D | 0.0497 (7) | 0.0363 (6) | 0.0413 (6) | 0.0182 (5) | 0.0178 (6) | 0.0161 (5) |
C2D | 0.0440 (8) | 0.0318 (7) | 0.0418 (7) | 0.0159 (6) | 0.0183 (6) | 0.0139 (6) |
N3D | 0.0420 (6) | 0.0354 (6) | 0.0439 (7) | 0.0135 (5) | 0.0179 (5) | 0.0171 (5) |
C4D | 0.0541 (9) | 0.0310 (7) | 0.0448 (8) | 0.0180 (6) | 0.0241 (7) | 0.0144 (6) |
C5D | 0.0574 (10) | 0.0379 (8) | 0.0574 (9) | 0.0169 (7) | 0.0292 (8) | 0.0186 (7) |
C6D | 0.0730 (12) | 0.0408 (8) | 0.0581 (10) | 0.0181 (8) | 0.0390 (9) | 0.0206 (8) |
C7D | 0.0852 (13) | 0.0400 (8) | 0.0485 (9) | 0.0243 (8) | 0.0361 (9) | 0.0212 (7) |
C8D | 0.0711 (11) | 0.0387 (8) | 0.0433 (8) | 0.0241 (8) | 0.0244 (8) | 0.0166 (7) |
C9D | 0.0569 (9) | 0.0337 (7) | 0.0424 (8) | 0.0201 (7) | 0.0231 (7) | 0.0152 (6) |
N10D | 0.0381 (6) | 0.0393 (6) | 0.0412 (6) | 0.0119 (5) | 0.0132 (5) | 0.0185 (5) |
C10D | 0.0393 (8) | 0.0453 (8) | 0.0480 (8) | 0.0112 (6) | 0.0143 (7) | 0.0191 (7) |
N11D | 0.0395 (6) | 0.0335 (6) | 0.0401 (6) | 0.0135 (5) | 0.0134 (5) | 0.0143 (5) |
C12D | 0.0366 (7) | 0.0310 (6) | 0.0425 (7) | 0.0105 (5) | 0.0152 (6) | 0.0129 (6) |
C13D | 0.0392 (7) | 0.0306 (6) | 0.0400 (7) | 0.0125 (5) | 0.0179 (6) | 0.0146 (6) |
N14D | 0.0359 (6) | 0.0322 (6) | 0.0419 (6) | 0.0119 (5) | 0.0169 (5) | 0.0159 (5) |
C14D | 0.0386 (7) | 0.0387 (7) | 0.0534 (9) | 0.0112 (6) | 0.0200 (7) | 0.0201 (7) |
C15D | 0.0400 (7) | 0.0428 (8) | 0.0427 (8) | 0.0156 (6) | 0.0162 (6) | 0.0204 (6) |
C16D | 0.0374 (7) | 0.0501 (9) | 0.0451 (8) | 0.0129 (6) | 0.0152 (6) | 0.0219 (7) |
N17D | 0.0369 (6) | 0.0407 (6) | 0.0430 (7) | 0.0106 (5) | 0.0166 (5) | 0.0184 (5) |
O1W | 0.0844 (11) | 0.1240 (14) | 0.0628 (9) | 0.0657 (10) | 0.0238 (8) | 0.0355 (9) |
O2W | 0.0435 (6) | 0.0457 (6) | 0.0804 (9) | 0.0159 (5) | 0.0200 (6) | 0.0241 (6) |
O3W | 0.0498 (7) | 0.0516 (7) | 0.0680 (8) | 0.0170 (5) | 0.0280 (6) | 0.0218 (6) |
O4W | 0.0419 (6) | 0.0533 (7) | 0.0596 (7) | 0.0092 (5) | 0.0178 (5) | 0.0294 (6) |
O5W | 0.0424 (6) | 0.0343 (5) | 0.0878 (9) | 0.0150 (5) | 0.0277 (6) | 0.0200 (6) |
N1A—C2A | 1.317 (2) | N3C—H3C | 0.8800 |
N1A—C9A | 1.398 (2) | C4C—C5C | 1.377 (3) |
C2A—N3A | 1.359 (2) | C4C—C9C | 1.405 (2) |
C2A—N10A | 1.3753 (19) | C5C—C6C | 1.396 (2) |
N3A—C4A | 1.390 (2) | C5C—H5C | 0.9500 |
N3A—H3A | 0.8800 | C6C—C7C | 1.393 (3) |
C4A—C5A | 1.386 (3) | C6C—H6C | 0.9500 |
C4A—C9A | 1.400 (3) | C7C—C8C | 1.384 (3) |
C5A—C6A | 1.389 (3) | C7C—H7C | 0.9500 |
C5A—H5A | 0.9500 | C8C—C9C | 1.397 (2) |
C6A—C7A | 1.385 (4) | C8C—H8C | 0.9500 |
C6A—H6A | 0.9500 | N10C—N11C | 1.3603 (17) |
C7A—C8A | 1.386 (3) | N10C—C10C | 1.448 (2) |
C7A—H7A | 0.9500 | C10C—H10G | 0.9800 |
C8A—C9A | 1.400 (3) | C10C—H10H | 0.9800 |
C8A—H8A | 0.9500 | C10C—H10I | 0.9800 |
N10A—N11A | 1.354 (2) | N11C—C12C | 1.287 (2) |
N10A—C10A | 1.450 (2) | C12C—C13C | 1.462 (2) |
C10A—H10A | 0.9800 | C12C—H12C | 0.9500 |
C10A—H10B | 0.9800 | C13C—N17C | 1.324 (2) |
C10A—H10C | 0.9800 | C13C—N14C | 1.361 (2) |
N11A—C12A | 1.2863 (19) | N14C—C15C | 1.368 (2) |
C12A—C13A | 1.443 (2) | N14C—C14C | 1.451 (3) |
C12A—H12A | 0.9500 | C14C—H14G | 0.9800 |
C13A—N17A | 1.333 (2) | C14C—H14H | 0.9800 |
C13A—N14A | 1.3639 (18) | C14C—H14I | 0.9800 |
N14A—C15A | 1.369 (2) | C15C—C16C | 1.361 (3) |
N14A—C14A | 1.462 (2) | C15C—H15C | 0.9500 |
C14A—H14A | 0.9800 | C16C—N17C | 1.372 (2) |
C14A—H14B | 0.9800 | C16C—H16C | 0.9500 |
C14A—H14C | 0.9800 | N1D—C2D | 1.319 (2) |
C15A—C16A | 1.364 (2) | N1D—C9D | 1.395 (2) |
C15A—H15A | 0.9500 | C2D—N3D | 1.3605 (19) |
C16A—N17A | 1.374 (2) | C2D—N10D | 1.3734 (18) |
C16A—H16A | 0.9500 | N3D—C4D | 1.3915 (19) |
N1B—C2B | 1.3250 (19) | N3D—H3D | 0.8800 |
N1B—C9B | 1.398 (2) | C4D—C5D | 1.388 (2) |
C2B—N3B | 1.359 (2) | C4D—C9D | 1.400 (2) |
C2B—N10B | 1.365 (2) | C5D—C6D | 1.385 (2) |
N3B—C4B | 1.3879 (18) | C5D—H5D | 0.9500 |
N3B—H3B | 0.8800 | C6D—C7D | 1.389 (3) |
C4B—C5B | 1.381 (2) | C6D—H6D | 0.9500 |
C4B—C9B | 1.408 (2) | C7D—C8D | 1.390 (3) |
C5B—C6B | 1.394 (2) | C7D—H7D | 0.9500 |
C5B—H5B | 0.9500 | C8D—C9D | 1.397 (2) |
C6B—C7B | 1.397 (2) | C8D—H8D | 0.9500 |
C6B—H6B | 0.9500 | N10D—N11D | 1.3556 (17) |
C7B—C8B | 1.388 (2) | N10D—C10D | 1.4477 (19) |
C7B—H7B | 0.9500 | C10D—H10J | 0.9800 |
C8B—C9B | 1.392 (2) | C10D—H10K | 0.9800 |
C8B—H8B | 0.9500 | C10D—H10L | 0.9800 |
N10B—N11B | 1.3624 (18) | N11D—C12D | 1.2832 (18) |
N10B—C10B | 1.447 (2) | C12D—C13D | 1.437 (2) |
C10B—H10D | 0.9800 | C12D—H12D | 0.9500 |
C10B—H10E | 0.9800 | C13D—N17D | 1.3317 (19) |
C10B—H10F | 0.9800 | C13D—N14D | 1.3669 (17) |
N11B—C12B | 1.283 (2) | N14D—C15D | 1.362 (2) |
C12B—C13B | 1.452 (2) | N14D—C14D | 1.4580 (18) |
C12B—H12B | 0.9500 | C14D—H14J | 0.9800 |
C13B—N17B | 1.330 (2) | C14D—H14K | 0.9800 |
C13B—N14B | 1.359 (2) | C14D—H14L | 0.9800 |
N14B—C15B | 1.365 (2) | C15D—C16D | 1.363 (2) |
N14B—C14B | 1.457 (2) | C15D—H15D | 0.9500 |
C14B—H14D | 0.9800 | C16D—N17D | 1.376 (2) |
C14B—H14E | 0.9800 | C16D—H16D | 0.9500 |
C14B—H14F | 0.9800 | O1W—H1WA | 0.8215 |
C15B—C16B | 1.364 (3) | O1W—H1WB | 1.0606 |
C15B—H15B | 0.9500 | O2W—H2WA | 0.8501 |
C16B—N17B | 1.375 (2) | O2W—H2WB | 0.9702 |
C16B—H16B | 0.9500 | O3W—H3WA | 0.8500 |
N1C—C2C | 1.3285 (18) | O3W—H3WB | 0.8501 |
N1C—C9C | 1.398 (2) | O4W—H4WA | 0.9715 |
C2C—N3C | 1.351 (2) | O4W—H4WB | 0.8580 |
C2C—N10C | 1.374 (2) | O5W—H5WA | 0.8398 |
N3C—C4C | 1.3882 (19) | O5W—H5WB | 0.8301 |
C2A—N1A—C9A | 103.78 (16) | N3C—C2C—N10C | 121.28 (13) |
N1A—C2A—N3A | 114.56 (14) | C2C—N3C—C4C | 106.68 (13) |
N1A—C2A—N10A | 123.71 (16) | C2C—N3C—H3C | 126.7 |
N3A—C2A—N10A | 121.71 (16) | C4C—N3C—H3C | 126.7 |
C2A—N3A—C4A | 106.10 (16) | C5C—C4C—N3C | 132.55 (15) |
C2A—N3A—H3A | 127.0 | C5C—C4C—C9C | 122.48 (15) |
C4A—N3A—H3A | 127.0 | N3C—C4C—C9C | 104.96 (15) |
C5A—C4A—N3A | 132.7 (2) | C4C—C5C—C6C | 117.20 (18) |
C5A—C4A—C9A | 121.98 (18) | C4C—C5C—H5C | 121.4 |
N3A—C4A—C9A | 105.29 (15) | C6C—C5C—H5C | 121.4 |
C4A—C5A—C6A | 116.7 (2) | C7C—C6C—C5C | 121.11 (19) |
C4A—C5A—H5A | 121.6 | C7C—C6C—H6C | 119.4 |
C6A—C5A—H5A | 121.6 | C5C—C6C—H6C | 119.4 |
C7A—C6A—C5A | 121.8 (2) | C8C—C7C—C6C | 121.40 (16) |
C7A—C6A—H6A | 119.1 | C8C—C7C—H7C | 119.3 |
C5A—C6A—H6A | 119.1 | C6C—C7C—H7C | 119.3 |
C6A—C7A—C8A | 121.8 (2) | C7C—C8C—C9C | 118.23 (17) |
C6A—C7A—H7A | 119.1 | C7C—C8C—H8C | 120.9 |
C8A—C7A—H7A | 119.1 | C9C—C8C—H8C | 120.9 |
C7A—C8A—C9A | 117.0 (3) | C8C—C9C—N1C | 129.92 (16) |
C7A—C8A—H8A | 121.5 | C8C—C9C—C4C | 119.58 (17) |
C9A—C8A—H8A | 121.5 | N1C—C9C—C4C | 110.50 (13) |
N1A—C9A—C4A | 110.27 (16) | N11C—N10C—C2C | 113.81 (14) |
N1A—C9A—C8A | 129.0 (2) | N11C—N10C—C10C | 123.92 (13) |
C4A—C9A—C8A | 120.69 (19) | C2C—N10C—C10C | 122.27 (13) |
N11A—N10A—C2A | 115.08 (14) | N10C—C10C—H10G | 109.5 |
N11A—N10A—C10A | 123.70 (12) | N10C—C10C—H10H | 109.5 |
C2A—N10A—C10A | 121.21 (15) | H10G—C10C—H10H | 109.5 |
N10A—C10A—H10A | 109.5 | N10C—C10C—H10I | 109.5 |
N10A—C10A—H10B | 109.5 | H10G—C10C—H10I | 109.5 |
H10A—C10A—H10B | 109.5 | H10H—C10C—H10I | 109.5 |
N10A—C10A—H10C | 109.5 | C12C—N11C—N10C | 120.35 (15) |
H10A—C10A—H10C | 109.5 | N11C—C12C—C13C | 115.28 (16) |
H10B—C10A—H10C | 109.5 | N11C—C12C—H12C | 122.4 |
C12A—N11A—N10A | 119.16 (13) | C13C—C12C—H12C | 122.4 |
N11A—C12A—C13A | 118.48 (14) | N17C—C13C—N14C | 111.55 (15) |
N11A—C12A—H12A | 120.8 | N17C—C13C—C12C | 124.43 (15) |
C13A—C12A—H12A | 120.8 | N14C—C13C—C12C | 124.02 (17) |
N17A—C13A—N14A | 111.08 (14) | C13C—N14C—C15C | 106.53 (16) |
N17A—C13A—C12A | 126.33 (13) | C13C—N14C—C14C | 128.00 (15) |
N14A—C13A—C12A | 122.54 (14) | C15C—N14C—C14C | 125.34 (15) |
C13A—N14A—C15A | 107.26 (13) | N14C—C14C—H14G | 109.5 |
C13A—N14A—C14A | 126.95 (14) | N14C—C14C—H14H | 109.5 |
C15A—N14A—C14A | 125.78 (13) | H14G—C14C—H14H | 109.5 |
N14A—C14A—H14A | 109.5 | N14C—C14C—H14I | 109.5 |
N14A—C14A—H14B | 109.5 | H14G—C14C—H14I | 109.5 |
H14A—C14A—H14B | 109.5 | H14H—C14C—H14I | 109.5 |
N14A—C14A—H14C | 109.5 | C16C—C15C—N14C | 106.55 (15) |
H14A—C14A—H14C | 109.5 | C16C—C15C—H15C | 126.7 |
H14B—C14A—H14C | 109.5 | N14C—C15C—H15C | 126.7 |
C16A—C15A—N14A | 105.98 (14) | C15C—C16C—N17C | 110.05 (18) |
C16A—C15A—H15A | 127.0 | C15C—C16C—H16C | 125.0 |
N14A—C15A—H15A | 127.0 | N17C—C16C—H16C | 125.0 |
C15A—C16A—N17A | 110.56 (15) | C13C—N17C—C16C | 105.31 (16) |
C15A—C16A—H16A | 124.7 | C2D—N1D—C9D | 103.61 (13) |
N17A—C16A—H16A | 124.7 | N1D—C2D—N3D | 114.82 (13) |
C13A—N17A—C16A | 105.12 (13) | N1D—C2D—N10D | 124.58 (14) |
C2B—N1B—C9B | 103.44 (12) | N3D—C2D—N10D | 120.60 (13) |
N1B—C2B—N3B | 114.71 (13) | C2D—N3D—C4D | 105.70 (13) |
N1B—C2B—N10B | 124.31 (14) | C2D—N3D—H3D | 127.1 |
N3B—C2B—N10B | 120.97 (13) | C4D—N3D—H3D | 127.1 |
C2B—N3B—C4B | 106.24 (12) | C5D—C4D—N3D | 131.83 (16) |
C2B—N3B—H3B | 126.9 | C5D—C4D—C9D | 122.71 (15) |
C4B—N3B—H3B | 126.9 | N3D—C4D—C9D | 105.46 (13) |
C5B—C4B—N3B | 132.40 (13) | C6D—C5D—C4D | 116.41 (18) |
C5B—C4B—C9B | 122.38 (13) | C6D—C5D—H5D | 121.8 |
N3B—C4B—C9B | 105.22 (13) | C4D—C5D—H5D | 121.8 |
C4B—C5B—C6B | 117.05 (14) | C5D—C6D—C7D | 121.78 (16) |
C4B—C5B—H5B | 121.5 | C5D—C6D—H6D | 119.1 |
C6B—C5B—H5B | 121.5 | C7D—C6D—H6D | 119.1 |
C5B—C6B—C7B | 121.28 (15) | C6D—C7D—C8D | 121.77 (16) |
C5B—C6B—H6B | 119.4 | C6D—C7D—H7D | 119.1 |
C7B—C6B—H6B | 119.4 | C8D—C7D—H7D | 119.1 |
C8B—C7B—C6B | 121.28 (14) | C7D—C8D—C9D | 117.27 (17) |
C8B—C7B—H7B | 119.4 | C7D—C8D—H8D | 121.4 |
C6B—C7B—H7B | 119.4 | C9D—C8D—H8D | 121.4 |
C7B—C8B—C9B | 118.12 (14) | N1D—C9D—C8D | 129.54 (16) |
C7B—C8B—H8B | 120.9 | N1D—C9D—C4D | 110.42 (13) |
C9B—C8B—H8B | 120.9 | C8D—C9D—C4D | 120.04 (15) |
C8B—C9B—N1B | 129.71 (14) | N11D—N10D—C2D | 114.96 (12) |
C8B—C9B—C4B | 119.89 (14) | N11D—N10D—C10D | 123.91 (12) |
N1B—C9B—C4B | 110.40 (12) | C2D—N10D—C10D | 120.79 (13) |
N11B—N10B—C2B | 114.33 (13) | N10D—C10D—H10J | 109.5 |
N11B—N10B—C10B | 123.33 (13) | N10D—C10D—H10K | 109.5 |
C2B—N10B—C10B | 122.09 (13) | H10J—C10D—H10K | 109.5 |
N10B—C10B—H10D | 109.5 | N10D—C10D—H10L | 109.5 |
N10B—C10B—H10E | 109.5 | H10J—C10D—H10L | 109.5 |
H10D—C10B—H10E | 109.5 | H10K—C10D—H10L | 109.5 |
N10B—C10B—H10F | 109.5 | C12D—N11D—N10D | 118.81 (13) |
H10D—C10B—H10F | 109.5 | N11D—C12D—C13D | 118.92 (13) |
H10E—C10B—H10F | 109.5 | N11D—C12D—H12D | 120.5 |
C12B—N11B—N10B | 119.05 (14) | C13D—C12D—H12D | 120.5 |
N11B—C12B—C13B | 117.95 (16) | N17D—C13D—N14D | 110.93 (13) |
N11B—C12B—H12B | 121.0 | N17D—C13D—C12D | 126.99 (12) |
C13B—C12B—H12B | 121.0 | N14D—C13D—C12D | 122.06 (13) |
N17B—C13B—N14B | 111.38 (14) | C15D—N14D—C13D | 107.45 (12) |
N17B—C13B—C12B | 125.96 (15) | C15D—N14D—C14D | 125.57 (12) |
N14B—C13B—C12B | 122.66 (16) | C13D—N14D—C14D | 126.98 (13) |
C13B—N14B—C15B | 106.99 (15) | N14D—C14D—H14J | 109.5 |
C13B—N14B—C14B | 126.85 (14) | N14D—C14D—H14K | 109.5 |
C15B—N14B—C14B | 126.15 (14) | H14J—C14D—H14K | 109.5 |
N14B—C14B—H14D | 109.5 | N14D—C14D—H14L | 109.5 |
N14B—C14B—H14E | 109.5 | H14J—C14D—H14L | 109.5 |
H14D—C14B—H14E | 109.5 | H14K—C14D—H14L | 109.5 |
N14B—C14B—H14F | 109.5 | N14D—C15D—C16D | 106.04 (13) |
H14D—C14B—H14F | 109.5 | N14D—C15D—H15D | 127.0 |
H14E—C14B—H14F | 109.5 | C16D—C15D—H15D | 127.0 |
C16B—C15B—N14B | 106.48 (15) | C15D—C16D—N17D | 110.57 (14) |
C16B—C15B—H15B | 126.8 | C15D—C16D—H16D | 124.7 |
N14B—C15B—H15B | 126.8 | N17D—C16D—H16D | 124.7 |
C15B—C16B—N17B | 109.95 (17) | C13D—N17D—C16D | 105.01 (12) |
C15B—C16B—H16B | 125.0 | H1WA—O1W—H1WB | 111.3 |
N17B—C16B—H16B | 125.0 | H2WA—O2W—H2WB | 102.5 |
C13B—N17B—C16B | 105.20 (15) | H3WA—O3W—H3WB | 104.5 |
C2C—N1C—C9C | 103.35 (14) | H4WA—O4W—H4WB | 104.9 |
N1C—C2C—N3C | 114.51 (14) | H5WA—O5W—H5WB | 102.2 |
N1C—C2C—N10C | 124.21 (15) | ||
C9A—N1A—C2A—N3A | 0.13 (17) | C9C—N1C—C2C—N3C | −0.70 (16) |
C9A—N1A—C2A—N10A | 178.88 (13) | C9C—N1C—C2C—N10C | 179.37 (13) |
N1A—C2A—N3A—C4A | −0.10 (17) | N1C—C2C—N3C—C4C | 0.17 (17) |
N10A—C2A—N3A—C4A | −178.88 (13) | N10C—C2C—N3C—C4C | −179.90 (13) |
C2A—N3A—C4A—C5A | −179.95 (17) | C2C—N3C—C4C—C5C | 179.59 (16) |
C2A—N3A—C4A—C9A | 0.03 (16) | C2C—N3C—C4C—C9C | 0.44 (15) |
N3A—C4A—C5A—C6A | −179.32 (16) | N3C—C4C—C5C—C6C | −178.06 (15) |
C9A—C4A—C5A—C6A | 0.7 (2) | C9C—C4C—C5C—C6C | 1.0 (2) |
C4A—C5A—C6A—C7A | −0.5 (3) | C4C—C5C—C6C—C7C | −0.4 (2) |
C5A—C6A—C7A—C8A | 0.1 (3) | C5C—C6C—C7C—C8C | −0.2 (3) |
C6A—C7A—C8A—C9A | 0.2 (3) | C6C—C7C—C8C—C9C | 0.1 (2) |
C2A—N1A—C9A—C4A | −0.10 (17) | C7C—C8C—C9C—N1C | 179.37 (15) |
C2A—N1A—C9A—C8A | −179.59 (17) | C7C—C8C—C9C—C4C | 0.4 (2) |
C5A—C4A—C9A—N1A | −179.97 (15) | C2C—N1C—C9C—C8C | −178.03 (15) |
N3A—C4A—C9A—N1A | 0.05 (17) | C2C—N1C—C9C—C4C | 0.97 (16) |
C5A—C4A—C9A—C8A | −0.4 (2) | C5C—C4C—C9C—C8C | −1.0 (2) |
N3A—C4A—C9A—C8A | 179.58 (14) | N3C—C4C—C9C—C8C | 178.23 (13) |
C7A—C8A—C9A—N1A | 179.40 (16) | C5C—C4C—C9C—N1C | 179.86 (14) |
C7A—C8A—C9A—C4A | 0.0 (2) | N3C—C4C—C9C—N1C | −0.89 (16) |
N1A—C2A—N10A—N11A | 179.94 (13) | N1C—C2C—N10C—N11C | −178.11 (13) |
N3A—C2A—N10A—N11A | −1.39 (19) | N3C—C2C—N10C—N11C | 1.96 (19) |
N1A—C2A—N10A—C10A | −0.5 (2) | N1C—C2C—N10C—C10C | 2.2 (2) |
N3A—C2A—N10A—C10A | 178.18 (13) | N3C—C2C—N10C—C10C | −177.72 (14) |
C2A—N10A—N11A—C12A | 179.05 (12) | C2C—N10C—N11C—C12C | −179.37 (13) |
C10A—N10A—N11A—C12A | −0.5 (2) | C10C—N10C—N11C—C12C | 0.3 (2) |
N10A—N11A—C12A—C13A | 177.81 (12) | N10C—N11C—C12C—C13C | −179.06 (12) |
N11A—C12A—C13A—N17A | −2.7 (2) | N11C—C12C—C13C—N17C | −1.9 (2) |
N11A—C12A—C13A—N14A | 179.99 (12) | N11C—C12C—C13C—N14C | 177.93 (14) |
N17A—C13A—N14A—C15A | −0.67 (15) | N17C—C13C—N14C—C15C | −0.56 (18) |
C12A—C13A—N14A—C15A | 176.96 (12) | C12C—C13C—N14C—C15C | 179.57 (14) |
N17A—C13A—N14A—C14A | 178.36 (13) | N17C—C13C—N14C—C14C | 175.50 (15) |
C12A—C13A—N14A—C14A | −4.0 (2) | C12C—C13C—N14C—C14C | −4.4 (3) |
C13A—N14A—C15A—C16A | 0.48 (15) | C13C—N14C—C15C—C16C | 0.56 (19) |
C14A—N14A—C15A—C16A | −178.57 (13) | C14C—N14C—C15C—C16C | −175.63 (16) |
N14A—C15A—C16A—N17A | −0.15 (16) | N14C—C15C—C16C—N17C | −0.4 (2) |
N14A—C13A—N17A—C16A | 0.57 (15) | N14C—C13C—N17C—C16C | 0.32 (19) |
C12A—C13A—N17A—C16A | −176.95 (13) | C12C—C13C—N17C—C16C | −179.81 (15) |
C15A—C16A—N17A—C13A | −0.25 (16) | C15C—C16C—N17C—C13C | 0.0 (2) |
C9B—N1B—C2B—N3B | −0.10 (16) | C9D—N1D—C2D—N3D | −0.35 (16) |
C9B—N1B—C2B—N10B | −179.47 (13) | C9D—N1D—C2D—N10D | 179.53 (13) |
N1B—C2B—N3B—C4B | 0.18 (16) | N1D—C2D—N3D—C4D | 0.69 (16) |
N10B—C2B—N3B—C4B | 179.58 (12) | N10D—C2D—N3D—C4D | −179.20 (12) |
C2B—N3B—C4B—C5B | 179.54 (14) | C2D—N3D—C4D—C5D | 179.21 (15) |
C2B—N3B—C4B—C9B | −0.18 (14) | C2D—N3D—C4D—C9D | −0.69 (15) |
N3B—C4B—C5B—C6B | −179.12 (14) | N3D—C4D—C5D—C6D | 179.11 (15) |
C9B—C4B—C5B—C6B | 0.6 (2) | C9D—C4D—C5D—C6D | −1.0 (2) |
C4B—C5B—C6B—C7B | −0.3 (2) | C4D—C5D—C6D—C7D | 0.0 (2) |
C5B—C6B—C7B—C8B | −0.5 (2) | C5D—C6D—C7D—C8D | 0.8 (3) |
C6B—C7B—C8B—C9B | 0.9 (2) | C6D—C7D—C8D—C9D | −0.5 (2) |
C7B—C8B—C9B—N1B | 178.78 (14) | C2D—N1D—C9D—C8D | 179.11 (15) |
C7B—C8B—C9B—C4B | −0.6 (2) | C2D—N1D—C9D—C4D | −0.13 (16) |
C2B—N1B—C9B—C8B | −179.44 (15) | C7D—C8D—C9D—N1D | −179.68 (14) |
C2B—N1B—C9B—C4B | −0.03 (15) | C7D—C8D—C9D—C4D | −0.5 (2) |
C5B—C4B—C9B—C8B | −0.2 (2) | C5D—C4D—C9D—N1D | −179.39 (13) |
N3B—C4B—C9B—C8B | 179.61 (12) | N3D—C4D—C9D—N1D | 0.52 (16) |
C5B—C4B—C9B—N1B | −179.63 (12) | C5D—C4D—C9D—C8D | 1.3 (2) |
N3B—C4B—C9B—N1B | 0.13 (15) | N3D—C4D—C9D—C8D | −178.80 (13) |
N1B—C2B—N10B—N11B | −175.56 (13) | N1D—C2D—N10D—N11D | −179.96 (13) |
N3B—C2B—N10B—N11B | 5.11 (19) | N3D—C2D—N10D—N11D | −0.09 (19) |
N1B—C2B—N10B—C10B | −1.1 (2) | N1D—C2D—N10D—C10D | −6.3 (2) |
N3B—C2B—N10B—C10B | 179.51 (14) | N3D—C2D—N10D—C10D | 173.53 (13) |
C2B—N10B—N11B—C12B | 175.37 (13) | C2D—N10D—N11D—C12D | 175.60 (12) |
C10B—N10B—N11B—C12B | 1.0 (2) | C10D—N10D—N11D—C12D | 2.2 (2) |
N10B—N11B—C12B—C13B | 179.75 (12) | N10D—N11D—C12D—C13D | 178.58 (12) |
N11B—C12B—C13B—N17B | −2.3 (2) | N11D—C12D—C13D—N17D | −0.4 (2) |
N11B—C12B—C13B—N14B | 178.10 (13) | N11D—C12D—C13D—N14D | −178.31 (12) |
N17B—C13B—N14B—C15B | −0.30 (17) | N17D—C13D—N14D—C15D | −0.39 (16) |
C12B—C13B—N14B—C15B | 179.38 (13) | C12D—C13D—N14D—C15D | 177.77 (13) |
N17B—C13B—N14B—C14B | 178.65 (14) | N17D—C13D—N14D—C14D | −179.85 (13) |
C12B—C13B—N14B—C14B | −1.7 (2) | C12D—C13D—N14D—C14D | −1.7 (2) |
C13B—N14B—C15B—C16B | 0.18 (17) | C13D—N14D—C15D—C16D | 0.18 (16) |
C14B—N14B—C15B—C16B | −178.78 (15) | C14D—N14D—C15D—C16D | 179.65 (13) |
N14B—C15B—C16B—N17B | −0.01 (19) | N14D—C15D—C16D—N17D | 0.08 (18) |
N14B—C13B—N17B—C16B | 0.29 (17) | N14D—C13D—N17D—C16D | 0.43 (16) |
C12B—C13B—N17B—C16B | −179.38 (14) | C12D—C13D—N17D—C16D | −177.63 (14) |
C15B—C16B—N17B—C13B | −0.17 (18) | C15D—C16D—N17D—C13D | −0.31 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3A—H3A···O5W | 0.88 | 2.04 | 2.918 (2) | 174 |
N3B—H3B···O2W | 0.88 | 2.00 | 2.8786 (17) | 176 |
N3C—H3C···O3W | 0.88 | 1.96 | 2.8309 (17) | 171 |
C10C—H10G···O1Wi | 0.98 | 2.60 | 3.542 (2) | 160 |
N3D—H3D···O4W | 0.88 | 2.10 | 2.9787 (18) | 176 |
O1W—H1WA···N1Dii | 0.82 | 2.09 | 2.903 (2) | 170 |
O2W—H2WA···O5W | 0.85 | 2.10 | 2.8738 (17) | 151 |
O2W—H2WB···N17B | 0.97 | 1.89 | 2.8558 (19) | 172 |
O3W—H3WA···O4W | 0.85 | 2.07 | 2.9076 (17) | 168 |
O3W—H3WB···N17C | 0.85 | 1.95 | 2.792 (2) | 172 |
O4W—H4WA···N17D | 0.97 | 1.93 | 2.8789 (16) | 164 |
O4W—H4WB···N1Ciii | 0.86 | 2.08 | 2.9361 (18) | 174 |
O5W—H5WA···N1Biv | 0.84 | 2.09 | 2.9107 (16) | 166 |
O5W—H5WB···N17A | 0.83 | 2.08 | 2.9012 (17) | 168 |
Symmetry codes: (i) x, y, z+1; (ii) x, y, z−1; (iii) x−1, y, z; (iv) x+1, y, z. |
C12H13N6+·CF3O3S−·H2O | F(000) = 840 |
Mr = 408.37 | Dx = 1.500 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9818 (5) Å | Cell parameters from 2227 reflections |
b = 9.5704 (5) Å | θ = 3.8–25.6° |
c = 21.1278 (12) Å | µ = 0.24 mm−1 |
β = 95.383 (5)° | T = 295 K |
V = 1808.12 (17) Å3 | Prism, colourless |
Z = 4 | 0.4 × 0.25 × 0.2 mm |
Rigaku Xcalibur Eos diffractometer | 3603 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 2782 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
Detector resolution: 16.2413 pixels mm-1 | θmax = 27.0°, θmin = 3.2° |
ω scans | h = −11→10 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −11→12 |
Tmin = 0.936, Tmax = 1.000 | l = −24→26 |
7345 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.060 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.168 | w = 1/[σ2(Fo2) + (0.0748P)2 + 1.3789P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3603 reflections | Δρmax = 0.56 e Å−3 |
293 parameters | Δρmin = −0.38 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.8811 (3) | 0.5516 (3) | 0.41351 (11) | 0.0539 (6) | |
C2 | 0.8038 (3) | 0.5451 (3) | 0.46349 (12) | 0.0459 (6) | |
N3 | 0.7686 (3) | 0.4143 (3) | 0.48062 (12) | 0.0490 (6) | |
H3 | 0.725 (3) | 0.391 (3) | 0.5096 (14) | 0.046 (8)* | |
C4 | 0.8295 (3) | 0.3244 (3) | 0.43831 (13) | 0.0504 (7) | |
C5 | 0.8274 (4) | 0.1801 (4) | 0.43244 (17) | 0.0651 (9) | |
H5 | 0.777 (4) | 0.122 (4) | 0.4631 (18) | 0.083 (12)* | |
C6 | 0.9011 (5) | 0.1249 (4) | 0.3836 (2) | 0.0761 (10) | |
H6 | 0.895 (4) | 0.030 (5) | 0.381 (2) | 0.098 (14)* | |
C7 | 0.9746 (4) | 0.2101 (5) | 0.34283 (19) | 0.0761 (11) | |
H7 | 1.028 (4) | 0.166 (4) | 0.3117 (18) | 0.078 (11)* | |
C8 | 0.9750 (4) | 0.3534 (4) | 0.34858 (17) | 0.0682 (9) | |
H8 | 1.025 (4) | 0.414 (4) | 0.3194 (18) | 0.078 (11)* | |
C9 | 0.9003 (3) | 0.4112 (3) | 0.39720 (13) | 0.0530 (7) | |
N10 | 0.7609 (3) | 0.6599 (2) | 0.49611 (11) | 0.0512 (6) | |
C10 | 0.8070 (4) | 0.8006 (3) | 0.48028 (15) | 0.0615 (8) | |
H10A | 0.7209 | 0.8535 | 0.4641 | 0.092* | |
H10B | 0.8768 | 0.7957 | 0.4486 | 0.092* | |
H10C | 0.8536 | 0.8452 | 0.5177 | 0.092* | |
N11 | 0.6765 (3) | 0.6323 (2) | 0.54464 (10) | 0.0464 (5) | |
C12 | 0.6314 (3) | 0.7334 (3) | 0.57690 (14) | 0.0497 (7) | |
H12 | 0.656 (3) | 0.820 (3) | 0.5692 (14) | 0.054 (8)* | |
C13 | 0.5439 (3) | 0.7007 (3) | 0.62923 (13) | 0.0452 (6) | |
N14 | 0.5057 (3) | 0.5664 (3) | 0.64411 (12) | 0.0491 (6) | |
H14 | 0.527 (4) | 0.501 (4) | 0.6236 (17) | 0.077 (12)* | |
C15 | 0.4250 (3) | 0.5691 (3) | 0.69324 (14) | 0.0521 (7) | |
H15 | 0.381 (3) | 0.492 (3) | 0.7137 (14) | 0.060 (9)* | |
N16 | 0.4099 (3) | 0.6999 (3) | 0.71078 (12) | 0.0531 (6) | |
H16 | 0.353 (4) | 0.729 (4) | 0.7424 (17) | 0.068 (10)* | |
C17 | 0.4832 (3) | 0.7837 (3) | 0.67137 (14) | 0.0534 (7) | |
H17 | 0.483 (3) | 0.883 (4) | 0.6767 (15) | 0.064 (9)* | |
C1A | 0.7593 (5) | 0.1925 (5) | 0.6715 (2) | 0.0921 (13) | |
F1A | 0.7374 (6) | 0.2944 (4) | 0.71194 (18) | 0.1793 (18) | |
F2A | 0.8792 (3) | 0.2204 (5) | 0.6460 (3) | 0.203 (2) | |
F3A | 0.7821 (4) | 0.0780 (4) | 0.70420 (18) | 0.1551 (14) | |
S1A | 0.59941 (9) | 0.17915 (7) | 0.61386 (4) | 0.0550 (3) | |
O1A | 0.6403 (5) | 0.0741 (3) | 0.57192 (16) | 0.1230 (13) | |
O2A | 0.4833 (3) | 0.1407 (4) | 0.65088 (18) | 0.1133 (12) | |
O3A | 0.5863 (3) | 0.3149 (2) | 0.58571 (11) | 0.0691 (7) | |
O1W | 0.2707 (3) | 0.7781 (3) | 0.81181 (12) | 0.0745 (7) | |
H1W1 | 0.310 (5) | 0.824 (5) | 0.843 (2) | 0.120 (18)* | |
H1W2 | 0.178 (5) | 0.743 (5) | 0.8232 (19) | 0.096 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0561 (14) | 0.0583 (15) | 0.0485 (13) | −0.0001 (11) | 0.0119 (11) | 0.0012 (11) |
C2 | 0.0481 (14) | 0.0464 (15) | 0.0429 (14) | 0.0020 (12) | 0.0025 (11) | 0.0014 (11) |
N3 | 0.0600 (14) | 0.0461 (13) | 0.0419 (13) | 0.0053 (11) | 0.0107 (11) | 0.0043 (10) |
C4 | 0.0532 (16) | 0.0530 (16) | 0.0446 (14) | 0.0112 (13) | 0.0034 (12) | 0.0009 (12) |
C5 | 0.081 (2) | 0.0513 (18) | 0.0631 (19) | 0.0162 (16) | 0.0071 (17) | −0.0040 (15) |
C6 | 0.088 (3) | 0.060 (2) | 0.080 (2) | 0.021 (2) | 0.006 (2) | −0.0157 (19) |
C7 | 0.073 (2) | 0.085 (3) | 0.071 (2) | 0.023 (2) | 0.0118 (18) | −0.020 (2) |
C8 | 0.061 (2) | 0.086 (3) | 0.0595 (19) | 0.0084 (18) | 0.0153 (16) | −0.0058 (18) |
C9 | 0.0470 (15) | 0.0630 (18) | 0.0488 (15) | 0.0080 (13) | 0.0031 (12) | −0.0021 (13) |
N10 | 0.0647 (15) | 0.0418 (12) | 0.0487 (13) | −0.0028 (11) | 0.0142 (11) | 0.0013 (10) |
C10 | 0.077 (2) | 0.0484 (17) | 0.0599 (18) | −0.0154 (15) | 0.0120 (16) | −0.0013 (14) |
N11 | 0.0546 (13) | 0.0422 (12) | 0.0431 (11) | 0.0005 (10) | 0.0080 (10) | 0.0009 (10) |
C12 | 0.0614 (17) | 0.0370 (15) | 0.0510 (16) | −0.0009 (13) | 0.0067 (13) | −0.0020 (12) |
C13 | 0.0520 (15) | 0.0365 (13) | 0.0467 (14) | 0.0024 (11) | 0.0025 (11) | −0.0032 (11) |
N14 | 0.0587 (14) | 0.0394 (13) | 0.0495 (13) | 0.0022 (11) | 0.0061 (11) | −0.0061 (11) |
C15 | 0.0589 (17) | 0.0487 (16) | 0.0492 (16) | −0.0014 (13) | 0.0073 (13) | −0.0021 (13) |
N16 | 0.0560 (14) | 0.0540 (15) | 0.0502 (13) | 0.0013 (11) | 0.0101 (11) | −0.0105 (11) |
C17 | 0.0640 (18) | 0.0407 (15) | 0.0560 (17) | 0.0014 (13) | 0.0081 (14) | −0.0083 (13) |
C1A | 0.074 (3) | 0.093 (3) | 0.105 (3) | 0.004 (2) | −0.009 (2) | 0.015 (3) |
F1A | 0.234 (5) | 0.155 (3) | 0.132 (3) | 0.008 (3) | −0.075 (3) | −0.045 (2) |
F2A | 0.0641 (17) | 0.268 (5) | 0.273 (5) | −0.040 (2) | 0.001 (2) | 0.096 (4) |
F3A | 0.133 (2) | 0.145 (3) | 0.176 (3) | 0.022 (2) | −0.047 (2) | 0.073 (2) |
S1A | 0.0621 (5) | 0.0394 (4) | 0.0640 (5) | 0.0011 (3) | 0.0082 (3) | 0.0052 (3) |
O1A | 0.211 (4) | 0.0481 (15) | 0.109 (2) | 0.0202 (19) | 0.010 (2) | −0.0251 (15) |
O2A | 0.0668 (16) | 0.124 (3) | 0.153 (3) | 0.0063 (16) | 0.0326 (18) | 0.064 (2) |
O3A | 0.1047 (18) | 0.0394 (11) | 0.0649 (13) | 0.0120 (11) | 0.0166 (12) | 0.0039 (10) |
O1W | 0.0820 (18) | 0.0836 (18) | 0.0609 (14) | −0.0136 (14) | 0.0227 (13) | −0.0227 (13) |
N1—C2 | 1.319 (3) | N11—C12 | 1.272 (3) |
N1—C9 | 1.402 (4) | C12—C13 | 1.450 (4) |
C2—N3 | 1.349 (4) | C12—H12 | 0.88 (3) |
C2—N10 | 1.371 (3) | C13—C17 | 1.346 (4) |
N3—C4 | 1.390 (4) | C13—N14 | 1.374 (3) |
N3—H3 | 0.79 (3) | N14—C15 | 1.321 (4) |
C4—C5 | 1.386 (4) | N14—H14 | 0.79 (4) |
C4—C9 | 1.398 (4) | C15—N16 | 1.316 (4) |
C5—C6 | 1.383 (5) | C15—H15 | 0.96 (3) |
C5—H5 | 0.99 (4) | N16—C17 | 1.369 (4) |
C6—C7 | 1.395 (6) | N16—H16 | 0.92 (4) |
C6—H6 | 0.91 (4) | C17—H17 | 0.96 (3) |
C7—C8 | 1.376 (5) | C1A—F2A | 1.276 (6) |
C7—H7 | 0.95 (4) | C1A—F3A | 1.301 (5) |
C8—C9 | 1.393 (4) | C1A—F1A | 1.324 (6) |
C8—H8 | 0.99 (4) | C1A—S1A | 1.798 (4) |
N10—N11 | 1.357 (3) | S1A—O2A | 1.410 (3) |
N10—C10 | 1.456 (4) | S1A—O1A | 1.411 (3) |
C10—H10A | 0.9600 | S1A—O3A | 1.429 (2) |
C10—H10B | 0.9600 | O1W—H1W1 | 0.85 (5) |
C10—H10C | 0.9600 | O1W—H1W2 | 0.95 (5) |
C2—N1—C9 | 103.8 (2) | H10B—C10—H10C | 109.5 |
N1—C2—N3 | 114.4 (2) | C12—N11—N10 | 119.0 (2) |
N1—C2—N10 | 124.0 (3) | N11—C12—C13 | 117.8 (3) |
N3—C2—N10 | 121.7 (2) | N11—C12—H12 | 122 (2) |
C2—N3—C4 | 106.6 (2) | C13—C12—H12 | 120 (2) |
C2—N3—H3 | 128 (2) | C17—C13—N14 | 106.0 (3) |
C4—N3—H3 | 125 (2) | C17—C13—C12 | 131.2 (3) |
C5—C4—N3 | 132.2 (3) | N14—C13—C12 | 122.8 (2) |
C5—C4—C9 | 122.7 (3) | C15—N14—C13 | 109.2 (2) |
N3—C4—C9 | 105.1 (3) | C15—N14—H14 | 129 (3) |
C6—C5—C4 | 116.4 (4) | C13—N14—H14 | 122 (3) |
C6—C5—H5 | 124 (2) | N16—C15—N14 | 108.6 (3) |
C4—C5—H5 | 120 (2) | N16—C15—H15 | 123.1 (19) |
C5—C6—C7 | 121.6 (4) | N14—C15—H15 | 128.4 (19) |
C5—C6—H6 | 113 (3) | C15—N16—C17 | 108.5 (3) |
C7—C6—H6 | 125 (3) | C15—N16—H16 | 125 (2) |
C8—C7—C6 | 121.7 (4) | C17—N16—H16 | 126 (2) |
C8—C7—H7 | 120 (2) | C13—C17—N16 | 107.7 (3) |
C6—C7—H7 | 118 (2) | C13—C17—H17 | 132.2 (19) |
C7—C8—C9 | 117.6 (4) | N16—C17—H17 | 120.1 (19) |
C7—C8—H8 | 122 (2) | F2A—C1A—F3A | 107.6 (4) |
C9—C8—H8 | 120 (2) | F2A—C1A—F1A | 107.5 (5) |
C8—C9—C4 | 120.0 (3) | F3A—C1A—F1A | 107.6 (5) |
C8—C9—N1 | 129.9 (3) | F2A—C1A—S1A | 112.4 (4) |
C4—C9—N1 | 110.1 (2) | F3A—C1A—S1A | 112.1 (3) |
N11—N10—C2 | 115.3 (2) | F1A—C1A—S1A | 109.4 (3) |
N11—N10—C10 | 123.0 (2) | O2A—S1A—O1A | 114.3 (2) |
C2—N10—C10 | 121.7 (2) | O2A—S1A—O3A | 115.59 (17) |
N10—C10—H10A | 109.5 | O1A—S1A—O3A | 113.71 (17) |
N10—C10—H10B | 109.5 | O2A—S1A—C1A | 103.2 (2) |
H10A—C10—H10B | 109.5 | O1A—S1A—C1A | 103.7 (2) |
N10—C10—H10C | 109.5 | O3A—S1A—C1A | 104.28 (19) |
H10A—C10—H10C | 109.5 | H1W1—O1W—H1W2 | 107 (4) |
C10H13N52+·2CF3O3S− | F(000) = 1016 |
Mr = 501.39 | Dx = 1.732 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.2524 (5) Å | Cell parameters from 4019 reflections |
b = 14.0242 (5) Å | θ = 3.1–27.8° |
c = 11.4488 (5) Å | µ = 0.38 mm−1 |
β = 102.259 (4)° | T = 295 K |
V = 1922.39 (14) Å3 | Prism, colourless |
Z = 4 | 0.45 × 0.2 × 0.15 mm |
Rigaku Xcalibur Eos diffractometer | 3929 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 2957 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 16.1544 pixels mm-1 | θmax = 26.5°, θmin = 3.1° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −17→17 |
Tmin = 0.955, Tmax = 1.000 | l = −13→14 |
19010 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.059P)2 + 1.1585P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.003 |
3929 reflections | Δρmax = 0.54 e Å−3 |
281 parameters | Δρmin = −0.32 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.20195 (18) | 0.84745 (15) | 0.5313 (2) | 0.0467 (5) | |
H1 | 0.2374 | 0.8141 | 0.4884 | 0.056* | |
C2 | 0.2058 (3) | 0.9428 (2) | 0.5228 (3) | 0.0572 (7) | |
H2 | 0.2451 | 0.9708 | 0.4705 | 0.069* | |
C3 | 0.1528 (3) | 0.9986 (2) | 0.5898 (3) | 0.0652 (9) | |
H3 | 0.1548 | 1.0648 | 0.5848 | 0.078* | |
C4 | 0.0956 (3) | 0.9533 (2) | 0.6662 (3) | 0.0654 (9) | |
H4 | 0.0589 | 0.9903 | 0.7133 | 0.078* | |
C5 | 0.0912 (2) | 0.8571 (2) | 0.6748 (3) | 0.0570 (8) | |
H5 | 0.0527 | 0.8287 | 0.7274 | 0.068* | |
C6 | 0.1456 (2) | 0.80102 (19) | 0.6032 (2) | 0.0427 (6) | |
N7 | 0.14560 (17) | 0.70476 (16) | 0.60157 (18) | 0.0426 (5) | |
C7 | 0.0859 (2) | 0.6461 (2) | 0.6734 (3) | 0.0541 (7) | |
H7A | 0.0369 | 0.6029 | 0.6221 | 0.081* | |
H7B | 0.0430 | 0.6865 | 0.7143 | 0.081* | |
H7C | 0.1388 | 0.6104 | 0.7308 | 0.081* | |
N8 | 0.20882 (17) | 0.66511 (14) | 0.53060 (18) | 0.0388 (5) | |
C9 | 0.2150 (2) | 0.57497 (18) | 0.5230 (2) | 0.0409 (6) | |
H9 | 0.1736 | 0.5346 | 0.5613 | 0.049* | |
C10 | 0.2900 (2) | 0.53860 (17) | 0.4515 (2) | 0.0394 (6) | |
N11 | 0.31405 (19) | 0.44784 (14) | 0.43736 (19) | 0.0462 (5) | |
H11 | 0.2847 | 0.4002 | 0.4667 | 0.055* | |
C12 | 0.3925 (2) | 0.4414 (2) | 0.3690 (3) | 0.0524 (7) | |
H12 | 0.4241 | 0.3858 | 0.3468 | 0.063* | |
C13 | 0.4152 (2) | 0.53037 (19) | 0.3401 (2) | 0.0498 (7) | |
H13 | 0.4652 | 0.5485 | 0.2935 | 0.060* | |
N14 | 0.35088 (17) | 0.58989 (15) | 0.39217 (18) | 0.0439 (5) | |
H14 | 0.3501 | 0.6511 | 0.3871 | 0.053* | |
S1A | 0.11671 (6) | 0.32082 (5) | 0.61625 (6) | 0.0454 (2) | |
O1A | 0.1761 (2) | 0.31792 (17) | 0.5216 (2) | 0.0777 (7) | |
O2A | 0.05228 (18) | 0.23784 (15) | 0.62733 (19) | 0.0670 (6) | |
O3A | 0.06083 (18) | 0.40887 (15) | 0.6250 (2) | 0.0681 (6) | |
C1A | 0.2271 (3) | 0.3193 (2) | 0.7483 (3) | 0.0711 (9) | |
F1A | 0.2736 (2) | 0.23723 (19) | 0.7680 (3) | 0.1312 (11) | |
F2A | 0.3049 (2) | 0.3810 (2) | 0.7382 (3) | 0.1349 (11) | |
F3A | 0.1874 (3) | 0.3408 (2) | 0.8440 (2) | 0.1325 (11) | |
S1B | 0.41086 (6) | 0.83315 (5) | 0.31694 (6) | 0.0444 (2) | |
O1B | 0.4542 (2) | 0.77597 (19) | 0.2363 (2) | 0.0817 (7) | |
O2B | 0.3858 (2) | 0.92845 (16) | 0.2831 (2) | 0.0821 (7) | |
O3B | 0.32475 (16) | 0.78518 (13) | 0.36507 (18) | 0.0537 (5) | |
C1B | 0.5234 (3) | 0.8416 (2) | 0.4480 (3) | 0.0631 (8) | |
F1B | 0.55674 (19) | 0.75603 (17) | 0.4874 (2) | 0.1023 (8) | |
F2B | 0.4907 (2) | 0.88692 (19) | 0.53512 (18) | 0.1051 (8) | |
F3B | 0.60951 (18) | 0.88743 (18) | 0.4238 (2) | 0.1053 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0469 (13) | 0.0412 (12) | 0.0577 (14) | −0.0014 (10) | 0.0237 (11) | −0.0083 (10) |
C2 | 0.0582 (18) | 0.0447 (16) | 0.074 (2) | −0.0041 (13) | 0.0257 (16) | −0.0035 (14) |
C3 | 0.064 (2) | 0.0416 (16) | 0.091 (2) | 0.0023 (14) | 0.0184 (18) | −0.0130 (15) |
C4 | 0.0594 (19) | 0.064 (2) | 0.077 (2) | 0.0102 (16) | 0.0255 (17) | −0.0204 (16) |
C5 | 0.0541 (17) | 0.0612 (18) | 0.0621 (18) | 0.0056 (14) | 0.0271 (15) | −0.0126 (14) |
C6 | 0.0345 (13) | 0.0506 (15) | 0.0449 (14) | 0.0008 (11) | 0.0125 (11) | −0.0075 (12) |
N7 | 0.0426 (12) | 0.0463 (12) | 0.0441 (12) | 0.0007 (9) | 0.0210 (10) | −0.0039 (9) |
C7 | 0.0563 (17) | 0.0630 (18) | 0.0518 (16) | −0.0054 (14) | 0.0313 (14) | 0.0004 (13) |
N8 | 0.0362 (11) | 0.0449 (12) | 0.0387 (11) | 0.0000 (9) | 0.0154 (9) | −0.0039 (9) |
C9 | 0.0415 (14) | 0.0416 (14) | 0.0432 (14) | −0.0021 (11) | 0.0172 (11) | −0.0005 (11) |
C10 | 0.0413 (14) | 0.0387 (13) | 0.0405 (13) | −0.0027 (11) | 0.0137 (11) | −0.0015 (10) |
N11 | 0.0558 (14) | 0.0352 (11) | 0.0537 (13) | −0.0022 (10) | 0.0251 (11) | −0.0010 (9) |
C12 | 0.0614 (18) | 0.0453 (15) | 0.0576 (17) | 0.0012 (13) | 0.0289 (15) | −0.0090 (13) |
C13 | 0.0535 (16) | 0.0494 (15) | 0.0550 (16) | −0.0022 (13) | 0.0306 (14) | −0.0075 (13) |
N14 | 0.0474 (13) | 0.0360 (11) | 0.0538 (13) | −0.0038 (9) | 0.0232 (11) | −0.0011 (9) |
S1A | 0.0458 (4) | 0.0469 (4) | 0.0472 (4) | −0.0047 (3) | 0.0180 (3) | 0.0049 (3) |
O1A | 0.0914 (17) | 0.0844 (17) | 0.0724 (15) | −0.0188 (13) | 0.0511 (14) | −0.0056 (12) |
O2A | 0.0694 (14) | 0.0625 (13) | 0.0738 (14) | −0.0238 (11) | 0.0252 (12) | −0.0023 (11) |
O3A | 0.0669 (14) | 0.0585 (13) | 0.0839 (15) | 0.0152 (11) | 0.0269 (12) | 0.0176 (11) |
C1A | 0.068 (2) | 0.062 (2) | 0.076 (2) | −0.0011 (18) | 0.0008 (19) | 0.0078 (17) |
F1A | 0.1041 (19) | 0.0985 (18) | 0.171 (3) | 0.0359 (15) | −0.0165 (18) | 0.0425 (18) |
F2A | 0.0938 (18) | 0.127 (2) | 0.158 (3) | −0.0570 (17) | −0.0312 (17) | 0.0225 (18) |
F3A | 0.155 (3) | 0.174 (3) | 0.0566 (14) | 0.018 (2) | −0.0034 (15) | −0.0068 (15) |
S1B | 0.0468 (4) | 0.0423 (4) | 0.0480 (4) | −0.0053 (3) | 0.0189 (3) | 0.0062 (3) |
O1B | 0.0789 (16) | 0.1037 (19) | 0.0753 (15) | −0.0141 (14) | 0.0452 (13) | −0.0260 (14) |
O2B | 0.0851 (17) | 0.0536 (13) | 0.0972 (17) | −0.0062 (12) | −0.0037 (14) | 0.0283 (12) |
O3B | 0.0482 (11) | 0.0496 (11) | 0.0710 (12) | −0.0050 (9) | 0.0298 (10) | −0.0009 (9) |
C1B | 0.061 (2) | 0.064 (2) | 0.063 (2) | −0.0101 (16) | 0.0091 (16) | 0.0114 (16) |
F1B | 0.0874 (16) | 0.0928 (16) | 0.1144 (17) | 0.0106 (12) | −0.0063 (13) | 0.0467 (13) |
F2B | 0.128 (2) | 0.121 (2) | 0.0613 (13) | −0.0191 (16) | 0.0084 (13) | −0.0195 (13) |
F3B | 0.0652 (13) | 0.128 (2) | 0.1133 (17) | −0.0455 (13) | −0.0020 (12) | 0.0242 (15) |
N1—C2 | 1.343 (3) | N11—C12 | 1.365 (3) |
N1—C6 | 1.349 (3) | N11—H11 | 0.8600 |
N1—H1 | 0.8600 | C12—C13 | 1.335 (4) |
C2—C3 | 1.354 (4) | C12—H12 | 0.9300 |
C2—H2 | 0.9300 | C13—N14 | 1.368 (3) |
C3—C4 | 1.386 (4) | C13—H13 | 0.9300 |
C3—H3 | 0.9300 | N14—H14 | 0.8600 |
C4—C5 | 1.354 (4) | S1A—O3A | 1.426 (2) |
C4—H4 | 0.9300 | S1A—O2A | 1.427 (2) |
C5—C6 | 1.403 (3) | S1A—O1A | 1.428 (2) |
C5—H5 | 0.9300 | S1A—C1A | 1.802 (4) |
C6—N7 | 1.350 (3) | C1A—F1A | 1.283 (4) |
N7—N8 | 1.355 (3) | C1A—F2A | 1.311 (4) |
N7—C7 | 1.464 (3) | C1A—F3A | 1.324 (4) |
C7—H7A | 0.9600 | S1B—O2B | 1.407 (2) |
C7—H7B | 0.9600 | S1B—O1B | 1.410 (2) |
C7—H7C | 0.9600 | S1B—O3B | 1.4548 (18) |
N8—C9 | 1.270 (3) | S1B—C1B | 1.813 (3) |
C9—C10 | 1.448 (3) | C1B—F3B | 1.315 (4) |
C9—H9 | 0.9300 | C1B—F2B | 1.315 (4) |
C10—N14 | 1.323 (3) | C1B—F1B | 1.316 (4) |
C10—N11 | 1.324 (3) | ||
C2—N1—C6 | 123.7 (2) | C10—N11—H11 | 125.2 |
C2—N1—H1 | 118.1 | C12—N11—H11 | 125.2 |
C6—N1—H1 | 118.1 | C13—C12—N11 | 106.8 (2) |
N1—C2—C3 | 120.4 (3) | C13—C12—H12 | 126.6 |
N1—C2—H2 | 119.8 | N11—C12—H12 | 126.6 |
C3—C2—H2 | 119.8 | C12—C13—N14 | 107.0 (2) |
C2—C3—C4 | 117.4 (3) | C12—C13—H13 | 126.5 |
C2—C3—H3 | 121.3 | N14—C13—H13 | 126.5 |
C4—C3—H3 | 121.3 | C10—N14—C13 | 109.4 (2) |
C5—C4—C3 | 122.4 (3) | C10—N14—H14 | 125.3 |
C5—C4—H4 | 118.8 | C13—N14—H14 | 125.3 |
C3—C4—H4 | 118.8 | O3A—S1A—O2A | 114.65 (14) |
C4—C5—C6 | 119.0 (3) | O3A—S1A—O1A | 114.07 (14) |
C4—C5—H5 | 120.5 | O2A—S1A—O1A | 115.14 (13) |
C6—C5—H5 | 120.5 | O3A—S1A—C1A | 103.71 (16) |
N1—C6—N7 | 118.2 (2) | O2A—S1A—C1A | 104.28 (15) |
N1—C6—C5 | 117.0 (3) | O1A—S1A—C1A | 102.93 (18) |
N7—C6—C5 | 124.8 (2) | F1A—C1A—F2A | 107.6 (3) |
C6—N7—N8 | 114.8 (2) | F1A—C1A—F3A | 106.6 (3) |
C6—N7—C7 | 123.6 (2) | F2A—C1A—F3A | 109.0 (3) |
N8—N7—C7 | 121.6 (2) | F1A—C1A—S1A | 112.6 (3) |
N7—C7—H7A | 109.5 | F2A—C1A—S1A | 110.4 (3) |
N7—C7—H7B | 109.5 | F3A—C1A—S1A | 110.5 (3) |
H7A—C7—H7B | 109.5 | O2B—S1B—O1B | 116.78 (17) |
N7—C7—H7C | 109.5 | O2B—S1B—O3B | 114.22 (14) |
H7A—C7—H7C | 109.5 | O1B—S1B—O3B | 112.95 (13) |
H7B—C7—H7C | 109.5 | O2B—S1B—C1B | 104.40 (15) |
C9—N8—N7 | 119.9 (2) | O1B—S1B—C1B | 104.66 (16) |
N8—C9—C10 | 116.3 (2) | O3B—S1B—C1B | 101.65 (13) |
N8—C9—H9 | 121.8 | F3B—C1B—F2B | 108.1 (3) |
C10—C9—H9 | 121.8 | F3B—C1B—F1B | 108.3 (3) |
N14—C10—N11 | 107.2 (2) | F2B—C1B—F1B | 107.6 (3) |
N14—C10—C9 | 126.4 (2) | F3B—C1B—S1B | 111.1 (2) |
N11—C10—C9 | 126.3 (2) | F2B—C1B—S1B | 111.0 (2) |
C10—N11—C12 | 109.6 (2) | F1B—C1B—S1B | 110.5 (2) |
C6—N1—C2—C3 | 1.1 (5) | N11—C10—N14—C13 | −0.4 (3) |
N1—C2—C3—C4 | 0.0 (5) | C9—C10—N14—C13 | 177.1 (3) |
C2—C3—C4—C5 | −0.2 (5) | C12—C13—N14—C10 | −0.1 (3) |
C3—C4—C5—C6 | −0.6 (5) | O3A—S1A—C1A—F1A | 167.5 (3) |
C2—N1—C6—N7 | 178.3 (3) | O2A—S1A—C1A—F1A | 47.1 (3) |
C2—N1—C6—C5 | −1.9 (4) | O1A—S1A—C1A—F1A | −73.4 (3) |
C4—C5—C6—N1 | 1.6 (4) | O3A—S1A—C1A—F2A | −72.2 (3) |
C4—C5—C6—N7 | −178.6 (3) | O2A—S1A—C1A—F2A | 167.5 (3) |
N1—C6—N7—N8 | 3.4 (3) | O1A—S1A—C1A—F2A | 46.9 (3) |
C5—C6—N7—N8 | −176.4 (2) | O3A—S1A—C1A—F3A | 48.4 (3) |
N1—C6—N7—C7 | −178.7 (2) | O2A—S1A—C1A—F3A | −71.9 (3) |
C5—C6—N7—C7 | 1.5 (4) | O1A—S1A—C1A—F3A | 167.5 (3) |
C6—N7—N8—C9 | 179.7 (2) | O2B—S1B—C1B—F3B | −58.3 (3) |
C7—N7—N8—C9 | 1.8 (4) | O1B—S1B—C1B—F3B | 64.9 (3) |
N7—N8—C9—C10 | −176.1 (2) | O3B—S1B—C1B—F3B | −177.4 (2) |
N8—C9—C10—N14 | −1.2 (4) | O2B—S1B—C1B—F2B | 62.1 (3) |
N8—C9—C10—N11 | 175.8 (2) | O1B—S1B—C1B—F2B | −174.7 (2) |
N14—C10—N11—C12 | 0.7 (3) | O3B—S1B—C1B—F2B | −57.0 (2) |
C9—C10—N11—C12 | −176.8 (3) | O2B—S1B—C1B—F1B | −178.6 (2) |
C10—N11—C12—C13 | −0.8 (3) | O1B—S1B—C1B—F1B | −55.3 (3) |
N11—C12—C13—N14 | 0.5 (3) | O3B—S1B—C1B—F1B | 62.4 (3) |
NCNN | NCCN | A/B | B/C | A/C | |
1A | 177.83 (12) | -5.8 (2) | 2.30 (15) | 7.57 (13) | 8.81 (11) |
1B | -174.34 (11) | 2.4 (2) | 7.33 (12) | 1.49 (12) | 6.70 (9) |
2A | -10.6 (3) | 4.4 (3) | 11.32 (19) | 12.0 (2) | 15.64 (13) |
2B | -4.3 (3) | -0.5 (3) | 4.39 (12) | 2.56 (15) | 2.67 (12) |
3A | -1.39 (19) | -2.8 (2) | 2.76 (16) | 3.99 (19) | 6.42 (10) |
3B | 5.10 (19) | -2.3 (2) | 4.89 (13) | 5.33 (15) | 6.07 (10) |
3C | 1.96 (19) | -1.9 (2) | 3.22 (13) | 1.52 (16) | 3.53 (10) |
3D | -0.09 (19) | -0.5 (2) | 2.61 (10) | 3.84 (14) | 6.03 (9) |
4 | -179.71 (15) | -2.1 (3) | 3.09 | 2.36 | 4.98 |
5 | -2.5 (4) | -1.5 (4) | 1.12 (16) | 0.8 (2) | 1.65 (17) |
6 | 3.4 (3) | -1.2 (4) | 6.4 (3) | 4.8 (3) | 9.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
1 | ||||
N11A—H11A···N13B | 0.938 (17) | 1.931 (18) | 2.8423 (16) | 163.5 (15) |
N11B—H11B···N13Ai | 0.895 (17) | 2.042 (17) | 2.8796 (18) | 155.3 (14) |
2 | ||||
N3A—H3A···O1W | 0.88 (2) | 2.08 (2) | 2.944 (3) | 168 (2) |
N14A—H14A···O1W | 1.02 (2) | 1.89 (2) | 2.904 (3) | 177 (2) |
N3B—H3B···O2W | 0.91 (2) | 2.00 (2) | 2.902 (3) | 172 (2) |
N14B—H14B···N17Aii | 1.00 (3) | 1.90 (3) | 2.894 (3) | 172 (2) |
O1W—H1W1···N12Biii | 1.00 (4) | 1.82 (4) | 2.813 (3) | 172 (3) |
O1W—H1W2···O2W | 0.82 (3) | 2.03 (3) | 2.854 (3) | 175 (3) |
O2W—H2W1···N1Aiv | 0.96 (4) | 1.88 (4) | 2.825 (3) | 167 (3) |
O2W—H2W2···N17B | 0.97 (3) | 1.93 (3) | 2.893 (2) | 175 (3) |
3 | ||||
N3A—H3A···O1W | 0.88 | 2.04 | 2.918 (2) | 174 |
N3B—H3B···O2W | 0.88 | 2.00 | 2.8786 (17) | 176 |
N3C—H3C···O3W | 0.88 | 1.96 | 2.8309 (17) | 171 |
N3D—H3D···O4W | 0.88 | 2.10 | 2.9787 (18) | 176 |
O1W—H1WA···N17A | 0.83 | 2.09 | 168 | |
O1W—H1WB···N1Dv | 0.82 | 2.09 | 2.903 (2) | 170 |
O2W—H2WA···N17B | 0.97 | 1.89 | 2.8558 (19) | 172 |
O2W—H2WB···O1W | 0.85 | 2.10 | 2.8738 (17) | 151 |
O3W—H3WA···N17C | 0.85 | 1.95 | 2.792 (2) | 172 |
O3W—H3WB···O4W | 0.85 | 2.07 | 2.9076 (17) | 168 |
O4W—H4WA···N17D | 0.97 | 1.93 | 2.8789 (16) | 164 |
O4W—H4WB···N1Cvi | 0.86 | 2.08 | 2.9361 (18) | 174 |
O5W—H5WA···N1Bvii | 0.84 | 2.09 | 2.9107 (16) | 166 |
O5W—H5WB···N17A | 0.83 | 2.08 | 2.9012 (17) | 168 |
4 | ||||
N14—H14···Cl1 | 0.87 (3) | 2.24 (3) | 3.0831 (18) | 162 (3) |
O1A—H1A···Cl1viii | 0.84 | 2.48 | 3.176 (2) | 141 |
5 | ||||
N3—H3···O3A | 0.79 (3) | 2.25 (3) | 3.032 (3) | 175 (3) |
N14—H14···O3A | 0.79 (4) | 2.05 (4) | 2.830 (3) | 170 (4) |
N16—H16···O1W | 0.92 (4) | 1.76 (4) | 2.680 (3) | 170 (3) |
O1W—H1W1···N1ix | 0.85 (5) | 1.96 (6) | 2.803 (4) | 173 (5) |
O1W—H1W2···O2Ax | 0.95 (5) | 1.88 (5) | 2.809 (4) | 168 (4) |
6 | ||||
N1—H1···O3B | 0.86 | 1.99 | 2.804 (3) | 159 |
N11—H11···O1A | 0.86 | 1.96 | 2.793 (3) | 162 |
N14—H14···O3B | 0.86 | 1.91 | 2.767 (3) | 171 |
Symmetry codes: (i) -x, y+1/2, -z+1/2; (ii) -x+1/2, y-1/2, -z+3/2; (iii) -x+1, -y, -z+1; (iv) -x+1, -y+1, -z+1; (v) x, y, z+1; (vi) x-1, y, z; (vii) x+1, y, z; (viii) -x+2, -y+1, -z+1; (ix) x-1/2, -y+3/2, z+1/2; (x) -x+1/2, y+1/2, -z+3/2. |