In the title compound, C
18H
14O
8·2C
6H
18N
3OP, one acid and two phosphoramide molecules are linked together by strong O—H
O hydrogen bonds. There are two crystallographically independent amide–acid assemblies in the asymmetric unit. Three of the four symmetry-independent phosphoramide molecules adopt propeller-like conformations. The crystal structure is additionally stabilized by C—H
O interactions.
Supporting information
CCDC reference: 642993
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.003 Å
- R factor = 0.035
- wR factor = 0.098
- Data-to-parameter ratio = 19.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.66 mm
PLAT213_ALERT_2_C Atom C59 has ADP max/min Ratio ............. 3.10 prola
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.90 Ratio
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.89 Ratio
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.65 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.58 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for P4 - N12 .. 5.18 su
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for P4
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N12
PLAT731_ALERT_1_C Bond Calc 0.81(3), Rep 0.815(10) ...... 3.00 su-Ra
O13 -H13O 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.81(3), Rep 0.815(10) ...... 3.00 su-Ra
O13 -H13O 1.555 1.555
PLAT736_ALERT_1_C H...A Calc 1.68(3), Rep 1.684(13) ...... 2.31 su-Ra
H3O -O19 1.555 1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C18 H14 O8
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3
C6 H18 N3 O P
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 6
C6 H18 N3 O P
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.48
From the CIF: _reflns_number_total 17538
Count of symmetry unique reflns 9591
Completeness (_total/calc) 182.86%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 7947
Fraction of Friedel pairs measured 0.829
Are heavy atom types Z>Si present yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C26 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C28 = . R
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
15 ALERT level C = Check and explain
5 ALERT level G = General alerts; check
7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
7 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
(-)-(2
R,3
R)-
O,
O'-Dibenzoyl-(2
R,3
R)-tartaric acid–hexamethylphosphoramide (1/2)
top
Crystal data top
C18H14O8·2C6H18N3OP | F(000) = 3056 |
Mr = 716.70 | Dx = 1.242 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 72558 reflections |
a = 12.2940 (2) Å | θ = 3.0–27.5° |
b = 19.1370 (3) Å | µ = 0.17 mm−1 |
c = 32.5842 (6) Å | T = 153 K |
V = 7666.1 (2) Å3 | Block, colorless |
Z = 8 | 0.66 × 0.60 × 0.43 mm |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 17538 independent reflections |
Radiation source: fine-focus sealed tube | 16986 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: empirical (using intensity measurements) (SHELXTL; Bruker, 1998) | h = −15→15 |
Tmin = 0.896, Tmax = 0.930 | k = −24→24 |
75480 measured reflections | l = −42→41 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.0611P)2 + 1.9189P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.099 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.65 e Å−3 |
17538 reflections | Δρmin = −0.35 e Å−3 |
905 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
4 restraints | Extinction coefficient: 0.00144 (18) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 7969 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.01 (4) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
P1 | 0.13863 (4) | 0.26509 (2) | 0.667800 (14) | 0.02901 (9) | |
P2 | 0.71607 (3) | 0.03102 (2) | 0.616460 (12) | 0.02503 (8) | |
P3 | −0.20907 (3) | −0.12980 (2) | 0.478180 (12) | 0.02244 (8) | |
P4 | −0.54515 (4) | −0.04960 (3) | 0.836700 (16) | 0.03801 (11) | |
O1 | 0.20609 (9) | −0.03026 (5) | 0.58923 (3) | 0.0237 (2) | |
O2 | 0.18329 (11) | −0.14392 (6) | 0.60546 (4) | 0.0324 (3) | |
O3 | 0.04013 (9) | −0.06667 (7) | 0.54276 (4) | 0.0311 (3) | |
O4 | 0.14125 (11) | −0.08164 (7) | 0.48638 (4) | 0.0368 (3) | |
O5 | 0.45881 (10) | −0.02727 (7) | 0.55845 (5) | 0.0372 (3) | |
O6 | 0.41509 (11) | 0.08578 (6) | 0.56581 (4) | 0.0347 (3) | |
O7 | 0.22425 (9) | 0.06768 (6) | 0.52593 (4) | 0.0263 (2) | |
O8 | 0.33128 (10) | 0.11084 (7) | 0.47587 (4) | 0.0370 (3) | |
O9 | −0.28699 (9) | 0.19469 (6) | 0.78833 (3) | 0.0251 (2) | |
O10 | −0.43071 (11) | 0.18114 (8) | 0.74633 (4) | 0.0416 (3) | |
O11 | −0.07661 (10) | 0.15476 (6) | 0.71719 (4) | 0.0311 (3) | |
O12 | −0.15101 (12) | 0.25775 (7) | 0.73419 (5) | 0.0423 (3) | |
O13 | −0.31018 (11) | 0.02309 (7) | 0.78817 (4) | 0.0358 (3) | |
O14 | −0.22739 (14) | 0.03867 (7) | 0.84878 (4) | 0.0433 (3) | |
O15 | −0.09648 (9) | 0.13906 (6) | 0.81715 (3) | 0.0266 (2) | |
O16 | 0.01587 (13) | 0.04707 (8) | 0.82515 (4) | 0.0483 (4) | |
O17 | 0.06665 (11) | 0.20278 (7) | 0.67135 (4) | 0.0368 (3) | |
O18 | 0.64841 (10) | −0.00655 (7) | 0.58574 (4) | 0.0356 (3) | |
O19 | −0.12337 (10) | −0.11772 (8) | 0.50950 (4) | 0.0394 (3) | |
O20 | −0.43284 (13) | −0.06244 (9) | 0.82249 (7) | 0.0623 (5) | |
N1 | 0.09442 (16) | 0.31830 (9) | 0.63265 (6) | 0.0465 (4) | |
N2 | 0.14431 (15) | 0.30533 (9) | 0.71213 (5) | 0.0414 (4) | |
N3 | 0.26349 (14) | 0.24666 (11) | 0.65334 (6) | 0.0480 (4) | |
N4 | 0.78128 (12) | −0.02690 (7) | 0.64458 (4) | 0.0289 (3) | |
N5 | 0.79852 (14) | 0.08470 (8) | 0.59218 (4) | 0.0360 (3) | |
N6 | 0.65271 (13) | 0.07917 (9) | 0.65082 (5) | 0.0371 (3) | |
N7 | −0.30990 (11) | −0.17658 (7) | 0.49573 (5) | 0.0295 (3) | |
N8 | −0.15703 (11) | −0.16987 (7) | 0.43845 (4) | 0.0278 (3) | |
N9 | −0.26322 (13) | −0.05615 (7) | 0.46299 (4) | 0.0316 (3) | |
N10 | −0.58744 (15) | 0.03168 (10) | 0.83515 (6) | 0.0480 (4) | |
N11 | −0.5503 (2) | −0.06998 (12) | 0.88550 (7) | 0.0683 (6) | |
N12 | −0.6314 (2) | −0.09688 (14) | 0.81113 (9) | 0.0795 (8) | |
C1 | 0.15722 (15) | 0.01362 (9) | 0.66674 (6) | 0.0323 (3) | |
H1 | 0.1754 | 0.0464 | 0.6468 | 0.039* | |
C2 | 0.13258 (17) | 0.03498 (10) | 0.70651 (6) | 0.0403 (4) | |
H2 | 0.1340 | 0.0822 | 0.7132 | 0.048* | |
C3 | 0.10596 (17) | −0.01397 (11) | 0.73617 (6) | 0.0411 (4) | |
H3 | 0.0901 | 0.0005 | 0.7628 | 0.049* | |
C4 | 0.10284 (16) | −0.08405 (11) | 0.72644 (6) | 0.0369 (4) | |
H4 | 0.0845 | −0.1166 | 0.7465 | 0.044* | |
C5 | 0.12703 (14) | −0.10627 (9) | 0.68687 (5) | 0.0314 (3) | |
H5 | 0.1249 | −0.1536 | 0.6804 | 0.038* | |
C6 | 0.15447 (12) | −0.05739 (8) | 0.65700 (5) | 0.0258 (3) | |
C7 | 0.18147 (12) | −0.08318 (8) | 0.61532 (5) | 0.0244 (3) | |
C8 | 0.23168 (12) | −0.05067 (8) | 0.54795 (5) | 0.0230 (3) | |
H8 | 0.2783 | −0.0922 | 0.5489 | 0.028* | |
C9 | 0.13058 (12) | −0.06770 (8) | 0.52232 (5) | 0.0239 (3) | |
C10 | 0.29524 (12) | 0.00866 (8) | 0.52880 (5) | 0.0245 (3) | |
H10 | 0.3177 | −0.0051 | 0.5011 | 0.029* | |
C11 | 0.39667 (12) | 0.02795 (8) | 0.55371 (5) | 0.0244 (3) | |
C12 | 0.25391 (13) | 0.11687 (9) | 0.49818 (5) | 0.0276 (3) | |
C13 | 0.17936 (13) | 0.17758 (9) | 0.49866 (5) | 0.0301 (3) | |
C14 | 0.09099 (17) | 0.18145 (11) | 0.52494 (7) | 0.0453 (5) | |
H14 | 0.0767 | 0.1451 | 0.5431 | 0.054* | |
C15 | 0.0240 (2) | 0.23953 (14) | 0.52412 (10) | 0.0668 (8) | |
H15 | −0.0342 | 0.2426 | 0.5423 | 0.080* | |
C16 | 0.0431 (2) | 0.29322 (12) | 0.49640 (9) | 0.0579 (6) | |
H16 | −0.0032 | 0.3316 | 0.4955 | 0.070* | |
C17 | 0.1300 (2) | 0.28926 (11) | 0.47059 (7) | 0.0505 (5) | |
H17 | 0.1434 | 0.3255 | 0.4522 | 0.061* | |
C18 | 0.19858 (17) | 0.23194 (11) | 0.47139 (6) | 0.0419 (4) | |
H18 | 0.2577 | 0.2298 | 0.4536 | 0.050* | |
C19 | −0.39103 (14) | 0.30002 (9) | 0.83090 (5) | 0.0297 (3) | |
H19 | −0.3155 | 0.2981 | 0.8324 | 0.036* | |
C20 | −0.44879 (16) | 0.34634 (10) | 0.85567 (5) | 0.0358 (4) | |
H20 | −0.4115 | 0.3762 | 0.8732 | 0.043* | |
C21 | −0.56111 (17) | 0.34828 (11) | 0.85433 (6) | 0.0404 (4) | |
H21 | −0.5994 | 0.3788 | 0.8712 | 0.048* | |
C22 | −0.61614 (17) | 0.30442 (14) | 0.82768 (7) | 0.0538 (6) | |
H22 | −0.6917 | 0.3054 | 0.8268 | 0.065* | |
C23 | −0.55983 (16) | 0.25921 (12) | 0.80239 (7) | 0.0443 (5) | |
H23 | −0.5975 | 0.2304 | 0.7843 | 0.053* | |
C24 | −0.44692 (13) | 0.25671 (8) | 0.80397 (5) | 0.0260 (3) | |
C25 | −0.38985 (13) | 0.20736 (8) | 0.77597 (5) | 0.0255 (3) | |
C26 | −0.22253 (12) | 0.15071 (8) | 0.76234 (4) | 0.0218 (3) | |
H26 | −0.2709 | 0.1248 | 0.7439 | 0.026* | |
C27 | −0.14554 (13) | 0.19533 (8) | 0.73655 (5) | 0.0242 (3) | |
C28 | −0.16136 (12) | 0.09907 (8) | 0.78918 (4) | 0.0232 (3) | |
H28 | −0.1133 | 0.0708 | 0.7718 | 0.028* | |
C29 | −0.23749 (14) | 0.05049 (8) | 0.81288 (5) | 0.0278 (3) | |
C30 | −0.01169 (14) | 0.10517 (9) | 0.83458 (5) | 0.0313 (3) | |
C31 | 0.04182 (14) | 0.14950 (10) | 0.86644 (5) | 0.0322 (4) | |
C32 | 0.00569 (14) | 0.21662 (9) | 0.87538 (5) | 0.0296 (3) | |
H32 | −0.0520 | 0.2358 | 0.8607 | 0.036* | |
C33 | 0.05573 (16) | 0.25512 (10) | 0.90620 (6) | 0.0373 (4) | |
H33 | 0.0318 | 0.3001 | 0.9122 | 0.045* | |
C34 | 0.14132 (18) | 0.22625 (14) | 0.92800 (7) | 0.0505 (5) | |
H34 | 0.1751 | 0.2521 | 0.9485 | 0.061* | |
C35 | 0.1771 (2) | 0.15907 (15) | 0.91945 (8) | 0.0632 (7) | |
H35 | 0.2341 | 0.1398 | 0.9344 | 0.076* | |
C36 | 0.1276 (2) | 0.12051 (13) | 0.88839 (7) | 0.0560 (6) | |
H36 | 0.1517 | 0.0756 | 0.8824 | 0.067* | |
C37 | −0.0223 (2) | 0.33556 (17) | 0.63343 (11) | 0.0722 (8) | |
H37A | −0.0515 | 0.3322 | 0.6062 | 0.087* | |
H37B | −0.0317 | 0.3823 | 0.6435 | 0.087* | |
H37C | −0.0597 | 0.3035 | 0.6511 | 0.087* | |
C38 | 0.1606 (3) | 0.36685 (16) | 0.60916 (9) | 0.0790 (9) | |
H38A | 0.1529 | 0.4130 | 0.6203 | 0.095* | |
H38B | 0.1371 | 0.3668 | 0.5811 | 0.095* | |
H38C | 0.2355 | 0.3528 | 0.6106 | 0.095* | |
C39 | 0.1845 (3) | 0.37679 (13) | 0.71519 (9) | 0.0651 (7) | |
H39A | 0.2530 | 0.3770 | 0.7293 | 0.078* | |
H39B | 0.1330 | 0.4047 | 0.7301 | 0.078* | |
H39C | 0.1939 | 0.3958 | 0.6882 | 0.078* | |
C40 | 0.13351 (18) | 0.26933 (14) | 0.75089 (7) | 0.0493 (5) | |
H40A | 0.0862 | 0.2955 | 0.7686 | 0.059* | |
H40B | 0.2038 | 0.2649 | 0.7635 | 0.059* | |
H40C | 0.1034 | 0.2237 | 0.7463 | 0.059* | |
C41 | 0.3505 (2) | 0.23795 (19) | 0.68172 (9) | 0.0696 (8) | |
H41A | 0.4170 | 0.2541 | 0.6695 | 0.083* | |
H41B | 0.3574 | 0.1894 | 0.6887 | 0.083* | |
H41C | 0.3357 | 0.2645 | 0.7061 | 0.083* | |
C42 | 0.2781 (2) | 0.20833 (19) | 0.61509 (10) | 0.0779 (10) | |
H42A | 0.2694 | 0.1592 | 0.6201 | 0.094* | |
H42B | 0.3496 | 0.2171 | 0.6045 | 0.094* | |
H42C | 0.2247 | 0.2235 | 0.5955 | 0.094* | |
C43 | 0.83819 (15) | −0.08261 (10) | 0.62267 (6) | 0.0354 (4) | |
H43A | 0.8392 | −0.1240 | 0.6393 | 0.042* | |
H43B | 0.9115 | −0.0682 | 0.6170 | 0.042* | |
H43C | 0.8013 | −0.0922 | 0.5973 | 0.042* | |
C44 | 0.8304 (2) | −0.01129 (13) | 0.68409 (6) | 0.0531 (6) | |
H44A | 0.9044 | 0.0033 | 0.6801 | 0.064* | |
H44B | 0.8289 | −0.0523 | 0.7010 | 0.064* | |
H44C | 0.7904 | 0.0255 | 0.6972 | 0.064* | |
C45 | 0.8866 (2) | 0.11865 (16) | 0.61478 (7) | 0.0657 (8) | |
H45A | 0.9071 | 0.1610 | 0.6010 | 0.079* | |
H45B | 0.9482 | 0.0878 | 0.6161 | 0.079* | |
H45C | 0.8625 | 0.1294 | 0.6421 | 0.079* | |
C46 | 0.82486 (19) | 0.07248 (11) | 0.54911 (6) | 0.0438 (5) | |
H46A | 0.8913 | 0.0463 | 0.5472 | 0.053* | |
H46B | 0.8336 | 0.1165 | 0.5354 | 0.053* | |
H46C | 0.7670 | 0.0466 | 0.5364 | 0.053* | |
C47 | 0.5724 (2) | 0.04252 (15) | 0.67619 (8) | 0.0599 (7) | |
H47A | 0.5038 | 0.0413 | 0.6621 | 0.072* | |
H47B | 0.5640 | 0.0666 | 0.7018 | 0.072* | |
H47C | 0.5967 | −0.0044 | 0.6812 | 0.072* | |
C48 | 0.6199 (3) | 0.15073 (13) | 0.64077 (7) | 0.0600 (7) | |
H48A | 0.6006 | 0.1750 | 0.6655 | 0.072* | |
H48B | 0.5584 | 0.1496 | 0.6226 | 0.072* | |
H48C | 0.6791 | 0.1745 | 0.6276 | 0.072* | |
C49 | −0.33702 (16) | −0.24654 (9) | 0.48281 (6) | 0.0359 (4) | |
H49A | −0.4091 | −0.2470 | 0.4715 | 0.043* | |
H49B | −0.3340 | −0.2775 | 0.5060 | 0.043* | |
H49C | −0.2860 | −0.2618 | 0.4624 | 0.043* | |
C50 | −0.37046 (17) | −0.15222 (11) | 0.53123 (7) | 0.0464 (5) | |
H50A | −0.3604 | −0.1842 | 0.5536 | 0.056* | |
H50B | −0.4464 | −0.1495 | 0.5245 | 0.056* | |
H50C | −0.3446 | −0.1068 | 0.5391 | 0.056* | |
C51 | −0.06732 (18) | −0.21887 (13) | 0.44291 (8) | 0.0506 (5) | |
H51A | −0.0156 | −0.2114 | 0.4213 | 0.061* | |
H51B | −0.0946 | −0.2658 | 0.4414 | 0.061* | |
H51C | −0.0326 | −0.2117 | 0.4690 | 0.061* | |
C52 | −0.21689 (16) | −0.17701 (9) | 0.40016 (5) | 0.0331 (3) | |
H52A | −0.2461 | −0.2234 | 0.3982 | 0.040* | |
H52B | −0.1688 | −0.1686 | 0.3775 | 0.040* | |
H52C | −0.2753 | −0.1437 | 0.3996 | 0.040* | |
C53 | −0.1895 (2) | −0.00054 (10) | 0.44965 (6) | 0.0462 (5) | |
H53A | −0.2146 | 0.0435 | 0.4601 | 0.055* | |
H53B | −0.1877 | 0.0010 | 0.4202 | 0.055* | |
H53C | −0.1177 | −0.0097 | 0.4599 | 0.055* | |
C54 | −0.37541 (18) | −0.04687 (12) | 0.44964 (7) | 0.0491 (5) | |
H54A | −0.3769 | −0.0383 | 0.4206 | 0.059* | |
H54B | −0.4069 | −0.0078 | 0.4638 | 0.059* | |
H54C | −0.4163 | −0.0884 | 0.4557 | 0.059* | |
C55 | −0.5286 (2) | 0.08434 (12) | 0.85847 (9) | 0.0582 (6) | |
H55A | −0.5795 | 0.1156 | 0.8712 | 0.070* | |
H55B | −0.4819 | 0.1102 | 0.8404 | 0.070* | |
H55C | −0.4855 | 0.0620 | 0.8792 | 0.070* | |
C56 | −0.6496 (3) | 0.05830 (18) | 0.80108 (10) | 0.0785 (9) | |
H56A | −0.6010 | 0.0744 | 0.7801 | 0.094* | |
H56B | −0.6942 | 0.0964 | 0.8102 | 0.094* | |
H56C | −0.6949 | 0.0218 | 0.7903 | 0.094* | |
C57 | −0.6298 (4) | −0.0437 (2) | 0.91505 (10) | 0.0934 (11) | |
H57A | −0.5990 | −0.0449 | 0.9421 | 0.112* | |
H57B | −0.6938 | −0.0724 | 0.9143 | 0.112* | |
H57C | −0.6487 | 0.0036 | 0.9082 | 0.112* | |
C58 | −0.4941 (4) | −0.13183 (18) | 0.89993 (11) | 0.0847 (10) | |
H58A | −0.5437 | −0.1706 | 0.9003 | 0.102* | |
H58B | −0.4670 | −0.1237 | 0.9271 | 0.102* | |
H58C | −0.4345 | −0.1422 | 0.8819 | 0.102* | |
C59 | −0.6148 (4) | −0.1272 (3) | 0.77356 (16) | 0.154 (3) | |
H59A | −0.5419 | −0.1180 | 0.7646 | 0.185* | 0.50 |
H59B | −0.6654 | −0.1082 | 0.7541 | 0.185* | 0.50 |
H59C | −0.6256 | −0.1768 | 0.7757 | 0.185* | 0.50 |
H59D | −0.6800 | −0.1507 | 0.7650 | 0.185* | 0.50 |
H59E | −0.5565 | −0.1604 | 0.7755 | 0.185* | 0.50 |
H59F | −0.5963 | −0.0919 | 0.7539 | 0.185* | 0.50 |
C60 | −0.7433 (3) | −0.1080 (2) | 0.82836 (13) | 0.1027 (14) | |
H60A | −0.7559 | −0.1571 | 0.8320 | 0.123* | |
H60B | −0.7963 | −0.0893 | 0.8097 | 0.123* | |
H60C | −0.7492 | −0.0846 | 0.8543 | 0.123* | |
H3O | −0.0120 (18) | −0.0784 (17) | 0.5287 (9) | 0.076 (10)* | |
H5O | 0.5180 (15) | −0.0169 (17) | 0.5680 (10) | 0.082 (10)* | |
H11O | −0.038 (2) | 0.1788 (13) | 0.7022 (7) | 0.060 (8)* | |
H13O | −0.341 (3) | −0.0103 (13) | 0.7983 (10) | 0.093 (12)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.02788 (19) | 0.02493 (19) | 0.0342 (2) | −0.00459 (15) | 0.00849 (16) | −0.00191 (16) |
P2 | 0.02070 (17) | 0.02834 (19) | 0.02606 (18) | 0.00089 (14) | −0.00294 (14) | −0.00823 (15) |
P3 | 0.02010 (16) | 0.02318 (17) | 0.02405 (16) | −0.00374 (14) | −0.00453 (14) | 0.00116 (14) |
P4 | 0.0329 (2) | 0.0340 (2) | 0.0472 (3) | −0.01166 (18) | 0.0121 (2) | −0.0117 (2) |
O1 | 0.0240 (5) | 0.0201 (5) | 0.0269 (5) | −0.0011 (4) | −0.0028 (4) | −0.0017 (4) |
O2 | 0.0425 (7) | 0.0214 (5) | 0.0334 (6) | −0.0005 (5) | −0.0018 (5) | −0.0017 (4) |
O3 | 0.0187 (5) | 0.0453 (7) | 0.0293 (6) | −0.0034 (5) | −0.0032 (4) | −0.0058 (5) |
O4 | 0.0306 (6) | 0.0492 (7) | 0.0306 (6) | −0.0063 (5) | 0.0016 (5) | −0.0102 (5) |
O5 | 0.0203 (5) | 0.0271 (6) | 0.0643 (9) | 0.0015 (5) | −0.0135 (5) | −0.0075 (6) |
O6 | 0.0345 (6) | 0.0261 (6) | 0.0436 (7) | −0.0006 (5) | −0.0067 (5) | −0.0070 (5) |
O7 | 0.0200 (5) | 0.0244 (5) | 0.0346 (6) | 0.0023 (4) | 0.0019 (4) | 0.0055 (4) |
O8 | 0.0308 (6) | 0.0430 (7) | 0.0374 (6) | 0.0005 (5) | 0.0074 (5) | 0.0071 (6) |
O9 | 0.0229 (5) | 0.0288 (5) | 0.0237 (5) | 0.0060 (4) | −0.0009 (4) | −0.0064 (4) |
O10 | 0.0338 (7) | 0.0541 (8) | 0.0369 (6) | 0.0146 (6) | −0.0122 (5) | −0.0212 (6) |
O11 | 0.0362 (6) | 0.0232 (6) | 0.0340 (6) | −0.0034 (5) | 0.0140 (5) | −0.0020 (5) |
O12 | 0.0451 (8) | 0.0238 (6) | 0.0581 (8) | 0.0041 (5) | 0.0113 (6) | 0.0055 (6) |
O13 | 0.0359 (7) | 0.0327 (6) | 0.0386 (7) | −0.0085 (5) | 0.0041 (5) | 0.0033 (5) |
O14 | 0.0661 (9) | 0.0390 (7) | 0.0248 (6) | −0.0044 (7) | 0.0084 (6) | 0.0014 (5) |
O15 | 0.0284 (5) | 0.0254 (5) | 0.0261 (5) | 0.0038 (4) | −0.0066 (4) | −0.0037 (4) |
O16 | 0.0600 (9) | 0.0449 (8) | 0.0400 (7) | 0.0277 (7) | −0.0174 (6) | −0.0161 (6) |
O17 | 0.0414 (7) | 0.0291 (6) | 0.0400 (6) | −0.0110 (5) | 0.0133 (6) | −0.0039 (5) |
O18 | 0.0221 (5) | 0.0439 (7) | 0.0407 (7) | 0.0030 (5) | −0.0090 (5) | −0.0177 (6) |
O19 | 0.0287 (6) | 0.0560 (8) | 0.0336 (6) | −0.0135 (6) | −0.0117 (5) | 0.0037 (6) |
O20 | 0.0418 (8) | 0.0420 (8) | 0.1029 (14) | −0.0042 (7) | 0.0335 (9) | 0.0149 (9) |
N1 | 0.0526 (10) | 0.0365 (9) | 0.0503 (10) | 0.0030 (8) | 0.0080 (8) | 0.0101 (8) |
N2 | 0.0431 (9) | 0.0391 (9) | 0.0420 (8) | −0.0114 (7) | 0.0096 (7) | −0.0117 (7) |
N3 | 0.0324 (8) | 0.0579 (11) | 0.0537 (10) | −0.0014 (7) | 0.0114 (7) | −0.0184 (9) |
N4 | 0.0276 (6) | 0.0314 (7) | 0.0275 (6) | −0.0011 (6) | −0.0014 (5) | −0.0027 (5) |
N5 | 0.0446 (9) | 0.0392 (8) | 0.0243 (6) | −0.0091 (7) | −0.0040 (6) | −0.0002 (6) |
N6 | 0.0353 (8) | 0.0373 (8) | 0.0385 (8) | 0.0043 (6) | 0.0035 (6) | −0.0139 (6) |
N7 | 0.0267 (7) | 0.0247 (7) | 0.0370 (7) | −0.0078 (5) | 0.0064 (6) | −0.0068 (5) |
N8 | 0.0217 (6) | 0.0309 (7) | 0.0309 (7) | 0.0038 (5) | −0.0012 (5) | 0.0007 (5) |
N9 | 0.0403 (8) | 0.0224 (6) | 0.0321 (7) | 0.0004 (6) | −0.0010 (6) | 0.0020 (5) |
N10 | 0.0457 (9) | 0.0409 (9) | 0.0573 (10) | −0.0014 (8) | −0.0091 (8) | −0.0124 (8) |
N11 | 0.0947 (18) | 0.0500 (11) | 0.0600 (12) | 0.0092 (12) | 0.0309 (13) | 0.0055 (10) |
N12 | 0.0653 (14) | 0.0755 (16) | 0.0976 (18) | −0.0112 (13) | −0.0007 (14) | −0.0527 (15) |
C1 | 0.0368 (9) | 0.0246 (8) | 0.0353 (8) | 0.0025 (6) | −0.0048 (7) | −0.0018 (6) |
C2 | 0.0451 (10) | 0.0321 (9) | 0.0436 (10) | 0.0073 (8) | −0.0022 (8) | −0.0122 (8) |
C3 | 0.0412 (10) | 0.0486 (11) | 0.0336 (9) | 0.0114 (8) | −0.0017 (8) | −0.0071 (8) |
C4 | 0.0355 (9) | 0.0421 (10) | 0.0333 (9) | 0.0071 (7) | 0.0025 (7) | 0.0046 (7) |
C5 | 0.0309 (8) | 0.0273 (8) | 0.0360 (8) | 0.0008 (6) | −0.0013 (7) | 0.0014 (7) |
C6 | 0.0212 (7) | 0.0252 (7) | 0.0311 (7) | 0.0027 (5) | −0.0038 (6) | −0.0022 (6) |
C7 | 0.0217 (7) | 0.0215 (7) | 0.0299 (7) | −0.0001 (5) | −0.0049 (6) | 0.0005 (6) |
C8 | 0.0189 (7) | 0.0217 (7) | 0.0284 (7) | 0.0000 (5) | −0.0019 (5) | −0.0023 (5) |
C9 | 0.0206 (6) | 0.0208 (7) | 0.0303 (7) | −0.0013 (5) | −0.0022 (6) | −0.0028 (6) |
C10 | 0.0189 (6) | 0.0232 (7) | 0.0313 (7) | −0.0004 (5) | −0.0005 (6) | −0.0004 (6) |
C11 | 0.0194 (6) | 0.0248 (7) | 0.0289 (7) | −0.0016 (5) | 0.0003 (5) | −0.0003 (6) |
C12 | 0.0238 (7) | 0.0300 (8) | 0.0291 (7) | −0.0032 (6) | −0.0030 (6) | 0.0034 (6) |
C13 | 0.0257 (7) | 0.0295 (8) | 0.0351 (8) | −0.0004 (6) | −0.0037 (6) | 0.0066 (7) |
C14 | 0.0374 (10) | 0.0389 (10) | 0.0596 (12) | 0.0111 (8) | 0.0136 (9) | 0.0212 (9) |
C15 | 0.0548 (14) | 0.0528 (13) | 0.0929 (19) | 0.0251 (11) | 0.0299 (14) | 0.0312 (14) |
C16 | 0.0501 (12) | 0.0417 (11) | 0.0820 (17) | 0.0159 (10) | −0.0002 (12) | 0.0245 (12) |
C17 | 0.0560 (13) | 0.0367 (10) | 0.0587 (13) | 0.0014 (9) | −0.0055 (10) | 0.0215 (9) |
C18 | 0.0393 (10) | 0.0402 (10) | 0.0462 (10) | −0.0023 (8) | 0.0012 (8) | 0.0159 (8) |
C19 | 0.0294 (8) | 0.0294 (8) | 0.0302 (7) | 0.0041 (6) | 0.0001 (6) | −0.0033 (6) |
C20 | 0.0416 (10) | 0.0343 (9) | 0.0315 (8) | 0.0082 (7) | −0.0023 (7) | −0.0090 (7) |
C21 | 0.0417 (10) | 0.0435 (10) | 0.0359 (9) | 0.0213 (8) | −0.0006 (8) | −0.0076 (8) |
C22 | 0.0304 (9) | 0.0699 (15) | 0.0612 (13) | 0.0212 (10) | −0.0080 (9) | −0.0266 (12) |
C23 | 0.0294 (9) | 0.0550 (12) | 0.0484 (10) | 0.0138 (8) | −0.0093 (8) | −0.0202 (9) |
C24 | 0.0269 (7) | 0.0268 (7) | 0.0243 (7) | 0.0079 (6) | −0.0013 (6) | −0.0004 (6) |
C25 | 0.0258 (7) | 0.0262 (7) | 0.0244 (7) | 0.0037 (6) | −0.0020 (6) | −0.0003 (6) |
C26 | 0.0225 (7) | 0.0222 (7) | 0.0209 (6) | 0.0018 (5) | 0.0008 (5) | −0.0040 (5) |
C27 | 0.0244 (7) | 0.0234 (7) | 0.0247 (7) | −0.0001 (6) | −0.0014 (6) | 0.0003 (5) |
C28 | 0.0256 (7) | 0.0232 (7) | 0.0209 (6) | 0.0019 (6) | 0.0004 (5) | −0.0028 (5) |
C29 | 0.0345 (8) | 0.0203 (7) | 0.0286 (7) | 0.0035 (6) | 0.0095 (6) | −0.0016 (6) |
C30 | 0.0332 (8) | 0.0370 (9) | 0.0237 (7) | 0.0112 (7) | −0.0051 (6) | −0.0038 (7) |
C31 | 0.0311 (8) | 0.0398 (9) | 0.0258 (7) | 0.0074 (7) | −0.0061 (6) | −0.0022 (7) |
C32 | 0.0273 (7) | 0.0344 (8) | 0.0271 (7) | −0.0026 (6) | 0.0003 (6) | 0.0001 (6) |
C33 | 0.0354 (9) | 0.0396 (10) | 0.0370 (9) | −0.0073 (8) | 0.0016 (7) | −0.0063 (7) |
C34 | 0.0422 (11) | 0.0671 (14) | 0.0421 (10) | −0.0035 (10) | −0.0113 (9) | −0.0188 (10) |
C35 | 0.0577 (14) | 0.0752 (17) | 0.0568 (13) | 0.0211 (12) | −0.0363 (12) | −0.0183 (12) |
C36 | 0.0574 (13) | 0.0598 (14) | 0.0508 (12) | 0.0276 (11) | −0.0276 (11) | −0.0175 (11) |
C37 | 0.0632 (17) | 0.0674 (17) | 0.086 (2) | 0.0261 (14) | −0.0074 (15) | 0.0074 (15) |
C38 | 0.114 (3) | 0.0542 (15) | 0.0683 (17) | −0.0291 (17) | 0.0071 (17) | 0.0264 (13) |
C39 | 0.0793 (18) | 0.0484 (13) | 0.0677 (15) | −0.0224 (12) | 0.0152 (14) | −0.0251 (12) |
C40 | 0.0396 (10) | 0.0691 (14) | 0.0393 (10) | −0.0070 (10) | −0.0029 (8) | −0.0105 (10) |
C41 | 0.0370 (12) | 0.102 (2) | 0.0692 (16) | 0.0155 (13) | 0.0081 (11) | 0.0011 (15) |
C42 | 0.0491 (14) | 0.105 (2) | 0.0797 (19) | −0.0085 (15) | 0.0266 (14) | −0.0491 (18) |
C43 | 0.0295 (8) | 0.0336 (9) | 0.0430 (9) | 0.0061 (7) | 0.0027 (7) | −0.0018 (7) |
C44 | 0.0734 (16) | 0.0507 (12) | 0.0352 (10) | 0.0100 (11) | −0.0203 (10) | −0.0047 (9) |
C45 | 0.0709 (16) | 0.0863 (19) | 0.0398 (11) | −0.0500 (15) | −0.0100 (11) | 0.0096 (12) |
C46 | 0.0595 (13) | 0.0409 (10) | 0.0311 (9) | 0.0036 (9) | 0.0073 (8) | −0.0007 (8) |
C47 | 0.0445 (12) | 0.0691 (16) | 0.0661 (15) | −0.0117 (11) | 0.0272 (11) | −0.0328 (13) |
C48 | 0.0840 (18) | 0.0503 (13) | 0.0457 (11) | 0.0329 (13) | −0.0053 (11) | −0.0173 (10) |
C49 | 0.0465 (10) | 0.0273 (8) | 0.0338 (8) | −0.0138 (7) | 0.0003 (7) | −0.0024 (7) |
C50 | 0.0383 (10) | 0.0419 (10) | 0.0590 (12) | −0.0150 (8) | 0.0227 (9) | −0.0192 (9) |
C51 | 0.0379 (10) | 0.0566 (13) | 0.0572 (12) | 0.0230 (9) | −0.0054 (9) | −0.0052 (10) |
C52 | 0.0414 (9) | 0.0329 (8) | 0.0251 (7) | 0.0022 (7) | 0.0013 (7) | 0.0002 (6) |
C53 | 0.0785 (15) | 0.0289 (9) | 0.0312 (8) | −0.0160 (9) | −0.0009 (9) | 0.0054 (7) |
C54 | 0.0475 (12) | 0.0496 (12) | 0.0503 (11) | 0.0241 (10) | −0.0042 (9) | 0.0054 (9) |
C55 | 0.0678 (16) | 0.0325 (10) | 0.0743 (16) | −0.0046 (10) | −0.0118 (13) | −0.0131 (10) |
C56 | 0.085 (2) | 0.0708 (18) | 0.0794 (19) | −0.0204 (16) | −0.0305 (17) | 0.0194 (16) |
C57 | 0.119 (3) | 0.098 (3) | 0.0636 (18) | 0.002 (2) | 0.0351 (19) | −0.0108 (18) |
C58 | 0.111 (3) | 0.0671 (19) | 0.0764 (19) | −0.0034 (19) | 0.0025 (19) | 0.0194 (16) |
C59 | 0.096 (3) | 0.210 (6) | 0.156 (4) | −0.002 (3) | −0.008 (3) | −0.146 (5) |
C60 | 0.082 (2) | 0.131 (3) | 0.095 (2) | −0.063 (2) | 0.0126 (19) | −0.025 (2) |
Geometric parameters (Å, º) top
P1—O17 | 1.4894 (13) | C21—H21 | 0.9300 |
P1—N1 | 1.6261 (18) | C22—C23 | 1.381 (3) |
P1—N2 | 1.6384 (16) | C22—H22 | 0.9300 |
P1—N3 | 1.6440 (17) | C23—C24 | 1.390 (2) |
P2—O18 | 1.4869 (12) | C23—H23 | 0.9300 |
P2—N5 | 1.6458 (16) | C24—C25 | 1.489 (2) |
P2—N6 | 1.6460 (15) | C26—C28 | 1.519 (2) |
P2—N4 | 1.6465 (15) | C26—C27 | 1.527 (2) |
P3—O19 | 1.4849 (12) | C26—H26 | 0.9800 |
P3—N7 | 1.6325 (14) | C28—C29 | 1.529 (2) |
P3—N8 | 1.6350 (14) | C28—H28 | 0.9800 |
P3—N9 | 1.6354 (15) | C30—C31 | 1.493 (2) |
P4—O20 | 1.4769 (16) | C31—C36 | 1.389 (3) |
P4—N12 | 1.624 (2) | C31—C32 | 1.390 (2) |
P4—N11 | 1.638 (2) | C32—C33 | 1.389 (2) |
P4—N10 | 1.641 (2) | C32—H32 | 0.9300 |
O1—C7 | 1.3564 (19) | C33—C34 | 1.385 (3) |
O1—C8 | 1.4355 (18) | C33—H33 | 0.9300 |
O2—C7 | 1.206 (2) | C34—C35 | 1.387 (4) |
O3—C9 | 1.2963 (19) | C34—H34 | 0.9300 |
O3—H3O | 0.819 (10) | C35—C36 | 1.393 (3) |
O4—C9 | 1.208 (2) | C35—H35 | 0.9300 |
O5—C11 | 1.313 (2) | C36—H36 | 0.9300 |
O5—H5O | 0.817 (10) | C37—H37A | 0.9600 |
O6—C11 | 1.196 (2) | C37—H37B | 0.9600 |
O7—C12 | 1.3552 (19) | C37—H37C | 0.9600 |
O7—C10 | 1.4304 (18) | C38—H38A | 0.9600 |
O8—C12 | 1.203 (2) | C38—H38B | 0.9600 |
O9—C25 | 1.3491 (19) | C38—H38C | 0.9600 |
O9—C26 | 1.4330 (17) | C39—H39A | 0.9600 |
O10—C25 | 1.199 (2) | C39—H39B | 0.9600 |
O11—C27 | 1.3111 (19) | C39—H39C | 0.9600 |
O11—H11O | 0.822 (10) | C40—H40A | 0.9600 |
O12—C27 | 1.199 (2) | C40—H40B | 0.9600 |
O13—C29 | 1.312 (2) | C40—H40C | 0.9600 |
O13—H13O | 0.815 (10) | C41—H41A | 0.9600 |
O14—C29 | 1.198 (2) | C41—H41B | 0.9600 |
O15—C30 | 1.3527 (19) | C41—H41C | 0.9600 |
O15—C28 | 1.4327 (18) | C42—H42A | 0.9600 |
O16—C30 | 1.202 (2) | C42—H42B | 0.9600 |
N1—C38 | 1.453 (3) | C42—H42C | 0.9600 |
N1—C37 | 1.472 (3) | C43—H43A | 0.9600 |
N2—C40 | 1.445 (3) | C43—H43B | 0.9600 |
N2—C39 | 1.457 (3) | C43—H43C | 0.9600 |
N3—C41 | 1.423 (3) | C44—H44A | 0.9600 |
N3—C42 | 1.457 (3) | C44—H44B | 0.9600 |
N4—C44 | 1.453 (2) | C44—H44C | 0.9600 |
N4—C43 | 1.461 (2) | C45—H45A | 0.9600 |
N5—C46 | 1.459 (2) | C45—H45B | 0.9600 |
N5—C45 | 1.462 (3) | C45—H45C | 0.9600 |
N6—C48 | 1.465 (3) | C46—H46A | 0.9600 |
N6—C47 | 1.467 (3) | C46—H46B | 0.9600 |
N7—C49 | 1.443 (2) | C46—H46C | 0.9600 |
N7—C50 | 1.452 (2) | C47—H47A | 0.9600 |
N8—C51 | 1.455 (2) | C47—H47B | 0.9600 |
N8—C52 | 1.455 (2) | C47—H47C | 0.9600 |
N9—C54 | 1.457 (3) | C48—H48A | 0.9600 |
N9—C53 | 1.464 (2) | C48—H48B | 0.9600 |
N10—C56 | 1.441 (3) | C48—H48C | 0.9600 |
N10—C55 | 1.455 (3) | C49—H49A | 0.9600 |
N11—C58 | 1.449 (4) | C49—H49B | 0.9600 |
N11—C57 | 1.461 (4) | C49—H49C | 0.9600 |
N12—C59 | 1.370 (4) | C50—H50A | 0.9600 |
N12—C60 | 1.501 (4) | C50—H50B | 0.9600 |
C1—C2 | 1.392 (3) | C50—H50C | 0.9600 |
C1—C6 | 1.396 (2) | C51—H51A | 0.9600 |
C1—H1 | 0.9300 | C51—H51B | 0.9600 |
C2—C3 | 1.385 (3) | C51—H51C | 0.9600 |
C2—H2 | 0.9300 | C52—H52A | 0.9600 |
C3—C4 | 1.379 (3) | C52—H52B | 0.9600 |
C3—H3 | 0.9300 | C52—H52C | 0.9600 |
C4—C5 | 1.390 (3) | C53—H53A | 0.9600 |
C4—H4 | 0.9300 | C53—H53B | 0.9600 |
C5—C6 | 1.391 (2) | C53—H53C | 0.9600 |
C5—H5 | 0.9300 | C54—H54A | 0.9600 |
C6—C7 | 1.483 (2) | C54—H54B | 0.9600 |
C8—C10 | 1.513 (2) | C54—H54C | 0.9600 |
C8—C9 | 1.532 (2) | C55—H55A | 0.9600 |
C8—H8 | 0.9800 | C55—H55B | 0.9600 |
C10—C11 | 1.533 (2) | C55—H55C | 0.9600 |
C10—H10 | 0.9800 | C56—H56A | 0.9600 |
C12—C13 | 1.480 (2) | C56—H56B | 0.9600 |
C13—C14 | 1.385 (3) | C56—H56C | 0.9600 |
C13—C18 | 1.388 (2) | C57—H57A | 0.9600 |
C14—C15 | 1.383 (3) | C57—H57B | 0.9600 |
C14—H14 | 0.9300 | C57—H57C | 0.9600 |
C15—C16 | 1.388 (3) | C58—H58A | 0.9600 |
C15—H15 | 0.9300 | C58—H58B | 0.9600 |
C16—C17 | 1.362 (4) | C58—H58C | 0.9600 |
C16—H16 | 0.9300 | C59—H59A | 0.9600 |
C17—C18 | 1.384 (3) | C59—H59B | 0.9600 |
C17—H17 | 0.9300 | C59—H59C | 0.9600 |
C18—H18 | 0.9300 | C59—H59D | 0.9600 |
C19—C24 | 1.389 (2) | C59—H59E | 0.9600 |
C19—C20 | 1.393 (2) | C59—H59F | 0.9600 |
C19—H19 | 0.9300 | C60—H60A | 0.9600 |
C20—C21 | 1.382 (3) | C60—H60B | 0.9600 |
C20—H20 | 0.9300 | C60—H60C | 0.9600 |
C21—C22 | 1.384 (3) | | |
| | | |
O17—P1—N1 | 110.94 (9) | C33—C32—H32 | 120.0 |
O17—P1—N2 | 109.46 (8) | C31—C32—H32 | 120.0 |
N1—P1—N2 | 109.93 (10) | C34—C33—C32 | 119.72 (18) |
O17—P1—N3 | 113.91 (9) | C34—C33—H33 | 120.1 |
N1—P1—N3 | 104.16 (10) | C32—C33—H33 | 120.1 |
N2—P1—N3 | 108.28 (10) | C33—C34—C35 | 120.53 (19) |
O18—P2—N5 | 108.83 (8) | C33—C34—H34 | 119.7 |
O18—P2—N6 | 117.64 (8) | C35—C34—H34 | 119.7 |
N5—P2—N6 | 105.61 (9) | C34—C35—C36 | 119.9 (2) |
O18—P2—N4 | 108.75 (8) | C34—C35—H35 | 120.1 |
N5—P2—N4 | 112.82 (8) | C36—C35—H35 | 120.1 |
N6—P2—N4 | 103.22 (8) | C31—C36—C35 | 119.6 (2) |
O19—P3—N7 | 112.54 (8) | C31—C36—H36 | 120.2 |
O19—P3—N8 | 109.85 (8) | C35—C36—H36 | 120.2 |
N7—P3—N8 | 108.50 (7) | N1—C37—H37A | 109.5 |
O19—P3—N9 | 111.26 (8) | N1—C37—H37B | 109.5 |
N7—P3—N9 | 105.64 (8) | H37A—C37—H37B | 109.5 |
N8—P3—N9 | 108.90 (7) | N1—C37—H37C | 109.5 |
O20—P4—N12 | 110.90 (13) | H37A—C37—H37C | 109.5 |
O20—P4—N11 | 107.49 (13) | H37B—C37—H37C | 109.5 |
N12—P4—N11 | 109.89 (16) | N1—C38—H38A | 109.5 |
O20—P4—N10 | 116.38 (10) | N1—C38—H38B | 109.5 |
N12—P4—N10 | 107.79 (13) | H38A—C38—H38B | 109.5 |
N11—P4—N10 | 104.08 (11) | N1—C38—H38C | 109.5 |
C7—O1—C8 | 115.66 (11) | H38A—C38—H38C | 109.5 |
C9—O3—H3O | 112 (2) | H38B—C38—H38C | 109.5 |
C11—O5—H5O | 112 (2) | N2—C39—H39A | 109.5 |
C12—O7—C10 | 115.34 (12) | N2—C39—H39B | 109.5 |
C25—O9—C26 | 116.58 (11) | H39A—C39—H39B | 109.5 |
C27—O11—H11O | 109 (2) | N2—C39—H39C | 109.5 |
C29—O13—H13O | 113 (3) | H39A—C39—H39C | 109.5 |
C30—O15—C28 | 116.11 (12) | H39B—C39—H39C | 109.5 |
C38—N1—C37 | 114.3 (2) | N2—C40—H40A | 109.5 |
C38—N1—P1 | 125.8 (2) | N2—C40—H40B | 109.5 |
C37—N1—P1 | 117.00 (18) | H40A—C40—H40B | 109.5 |
C40—N2—C39 | 114.76 (19) | N2—C40—H40C | 109.5 |
C40—N2—P1 | 122.86 (14) | H40A—C40—H40C | 109.5 |
C39—N2—P1 | 121.05 (16) | H40B—C40—H40C | 109.5 |
C41—N3—C42 | 113.9 (2) | N3—C41—H41A | 109.5 |
C41—N3—P1 | 122.70 (16) | N3—C41—H41B | 109.5 |
C42—N3—P1 | 117.89 (17) | H41A—C41—H41B | 109.5 |
C44—N4—C43 | 112.57 (16) | N3—C41—H41C | 109.5 |
C44—N4—P2 | 123.85 (13) | H41A—C41—H41C | 109.5 |
C43—N4—P2 | 116.90 (12) | H41B—C41—H41C | 109.5 |
C46—N5—C45 | 113.02 (18) | N3—C42—H42A | 109.5 |
C46—N5—P2 | 119.93 (14) | N3—C42—H42B | 109.5 |
C45—N5—P2 | 119.44 (13) | H42A—C42—H42B | 109.5 |
C48—N6—C47 | 112.8 (2) | N3—C42—H42C | 109.5 |
C48—N6—P2 | 120.12 (15) | H42A—C42—H42C | 109.5 |
C47—N6—P2 | 115.75 (14) | H42B—C42—H42C | 109.5 |
C49—N7—C50 | 114.32 (14) | N4—C43—H43A | 109.5 |
C49—N7—P3 | 125.61 (12) | N4—C43—H43B | 109.5 |
C50—N7—P3 | 119.48 (11) | H43A—C43—H43B | 109.5 |
C51—N8—C52 | 114.11 (15) | N4—C43—H43C | 109.5 |
C51—N8—P3 | 121.32 (13) | H43A—C43—H43C | 109.5 |
C52—N8—P3 | 121.67 (11) | H43B—C43—H43C | 109.5 |
C54—N9—C53 | 114.14 (17) | N4—C44—H44A | 109.5 |
C54—N9—P3 | 125.50 (14) | N4—C44—H44B | 109.5 |
C53—N9—P3 | 117.66 (14) | H44A—C44—H44B | 109.5 |
C56—N10—C55 | 114.9 (2) | N4—C44—H44C | 109.5 |
C56—N10—P4 | 121.80 (19) | H44A—C44—H44C | 109.5 |
C55—N10—P4 | 118.88 (16) | H44B—C44—H44C | 109.5 |
C58—N11—C57 | 112.7 (3) | N5—C45—H45A | 109.5 |
C58—N11—P4 | 119.4 (2) | N5—C45—H45B | 109.5 |
C57—N11—P4 | 125.7 (2) | H45A—C45—H45B | 109.5 |
C59—N12—C60 | 114.2 (3) | N5—C45—H45C | 109.5 |
C59—N12—P4 | 126.7 (3) | H45A—C45—H45C | 109.5 |
C60—N12—P4 | 119.0 (2) | H45B—C45—H45C | 109.5 |
C2—C1—C6 | 119.49 (17) | N5—C46—H46A | 109.5 |
C2—C1—H1 | 120.3 | N5—C46—H46B | 109.5 |
C6—C1—H1 | 120.3 | H46A—C46—H46B | 109.5 |
C3—C2—C1 | 120.15 (18) | N5—C46—H46C | 109.5 |
C3—C2—H2 | 119.9 | H46A—C46—H46C | 109.5 |
C1—C2—H2 | 119.9 | H46B—C46—H46C | 109.5 |
C4—C3—C2 | 120.27 (18) | N6—C47—H47A | 109.5 |
C4—C3—H3 | 119.9 | N6—C47—H47B | 109.5 |
C2—C3—H3 | 119.9 | H47A—C47—H47B | 109.5 |
C3—C4—C5 | 120.33 (18) | N6—C47—H47C | 109.5 |
C3—C4—H4 | 119.8 | H47A—C47—H47C | 109.5 |
C5—C4—H4 | 119.8 | H47B—C47—H47C | 109.5 |
C4—C5—C6 | 119.68 (16) | N6—C48—H48A | 109.5 |
C4—C5—H5 | 120.2 | N6—C48—H48B | 109.5 |
C6—C5—H5 | 120.2 | H48A—C48—H48B | 109.5 |
C5—C6—C1 | 120.09 (16) | N6—C48—H48C | 109.5 |
C5—C6—C7 | 118.11 (14) | H48A—C48—H48C | 109.5 |
C1—C6—C7 | 121.80 (15) | H48B—C48—H48C | 109.5 |
O2—C7—O1 | 123.26 (15) | N7—C49—H49A | 109.5 |
O2—C7—C6 | 124.68 (15) | N7—C49—H49B | 109.5 |
O1—C7—C6 | 112.06 (13) | H49A—C49—H49B | 109.5 |
O1—C8—C10 | 107.18 (12) | N7—C49—H49C | 109.5 |
O1—C8—C9 | 113.00 (12) | H49A—C49—H49C | 109.5 |
C10—C8—C9 | 110.72 (13) | H49B—C49—H49C | 109.5 |
O1—C8—H8 | 108.6 | N7—C50—H50A | 109.5 |
C10—C8—H8 | 108.6 | N7—C50—H50B | 109.5 |
C9—C8—H8 | 108.6 | H50A—C50—H50B | 109.5 |
O4—C9—O3 | 126.47 (14) | N7—C50—H50C | 109.5 |
O4—C9—C8 | 119.15 (14) | H50A—C50—H50C | 109.5 |
O3—C9—C8 | 114.36 (13) | H50B—C50—H50C | 109.5 |
O7—C10—C8 | 107.72 (12) | N8—C51—H51A | 109.5 |
O7—C10—C11 | 109.92 (12) | N8—C51—H51B | 109.5 |
C8—C10—C11 | 112.49 (13) | H51A—C51—H51B | 109.5 |
O7—C10—H10 | 108.9 | N8—C51—H51C | 109.5 |
C8—C10—H10 | 108.9 | H51A—C51—H51C | 109.5 |
C11—C10—H10 | 108.9 | H51B—C51—H51C | 109.5 |
O6—C11—O5 | 126.55 (15) | N8—C52—H52A | 109.5 |
O6—C11—C10 | 123.45 (14) | N8—C52—H52B | 109.5 |
O5—C11—C10 | 109.98 (13) | H52A—C52—H52B | 109.5 |
O8—C12—O7 | 123.33 (15) | N8—C52—H52C | 109.5 |
O8—C12—C13 | 124.86 (15) | H52A—C52—H52C | 109.5 |
O7—C12—C13 | 111.82 (13) | H52B—C52—H52C | 109.5 |
C14—C13—C18 | 119.28 (17) | N9—C53—H53A | 109.5 |
C14—C13—C12 | 122.29 (15) | N9—C53—H53B | 109.5 |
C18—C13—C12 | 118.43 (16) | H53A—C53—H53B | 109.5 |
C15—C14—C13 | 119.85 (19) | N9—C53—H53C | 109.5 |
C15—C14—H14 | 120.1 | H53A—C53—H53C | 109.5 |
C13—C14—H14 | 120.1 | H53B—C53—H53C | 109.5 |
C14—C15—C16 | 120.5 (2) | N9—C54—H54A | 109.5 |
C14—C15—H15 | 119.8 | N9—C54—H54B | 109.5 |
C16—C15—H15 | 119.8 | H54A—C54—H54B | 109.5 |
C17—C16—C15 | 119.5 (2) | N9—C54—H54C | 109.5 |
C17—C16—H16 | 120.2 | H54A—C54—H54C | 109.5 |
C15—C16—H16 | 120.2 | H54B—C54—H54C | 109.5 |
C16—C17—C18 | 120.70 (19) | N10—C55—H55A | 109.5 |
C16—C17—H17 | 119.7 | N10—C55—H55B | 109.5 |
C18—C17—H17 | 119.7 | H55A—C55—H55B | 109.5 |
C17—C18—C13 | 120.16 (19) | N10—C55—H55C | 109.5 |
C17—C18—H18 | 119.9 | H55A—C55—H55C | 109.5 |
C13—C18—H18 | 119.9 | H55B—C55—H55C | 109.5 |
C24—C19—C20 | 119.57 (16) | N10—C56—H56A | 109.5 |
C24—C19—H19 | 120.2 | N10—C56—H56B | 109.5 |
C20—C19—H19 | 120.2 | H56A—C56—H56B | 109.5 |
C21—C20—C19 | 120.53 (17) | N10—C56—H56C | 109.5 |
C21—C20—H20 | 119.7 | H56A—C56—H56C | 109.5 |
C19—C20—H20 | 119.7 | H56B—C56—H56C | 109.5 |
C20—C21—C22 | 119.46 (17) | N11—C57—H57A | 109.5 |
C20—C21—H21 | 120.3 | N11—C57—H57B | 109.5 |
C22—C21—H21 | 120.3 | H57A—C57—H57B | 109.5 |
C23—C22—C21 | 120.61 (19) | N11—C57—H57C | 109.5 |
C23—C22—H22 | 119.7 | H57A—C57—H57C | 109.5 |
C21—C22—H22 | 119.7 | H57B—C57—H57C | 109.5 |
C22—C23—C24 | 120.01 (18) | N11—C58—H58A | 109.5 |
C22—C23—H23 | 120.0 | N11—C58—H58B | 109.5 |
C24—C23—H23 | 120.0 | H58A—C58—H58B | 109.5 |
C19—C24—C23 | 119.80 (15) | N11—C58—H58C | 109.5 |
C19—C24—C25 | 122.18 (14) | H58A—C58—H58C | 109.5 |
C23—C24—C25 | 118.02 (15) | H58B—C58—H58C | 109.5 |
O10—C25—O9 | 123.92 (15) | N12—C59—H59A | 109.5 |
O10—C25—C24 | 124.18 (15) | N12—C59—H59B | 109.5 |
O9—C25—C24 | 111.89 (13) | H59A—C59—H59B | 109.5 |
O9—C26—C28 | 108.40 (11) | N12—C59—H59C | 109.5 |
O9—C26—C27 | 109.85 (12) | H59A—C59—H59C | 109.5 |
C28—C26—C27 | 111.95 (12) | H59B—C59—H59C | 109.5 |
O9—C26—H26 | 108.9 | N12—C59—H59D | 109.5 |
C28—C26—H26 | 108.9 | H59A—C59—H59D | 141.1 |
C27—C26—H26 | 108.9 | H59B—C59—H59D | 56.3 |
O12—C27—O11 | 126.54 (15) | H59C—C59—H59D | 56.3 |
O12—C27—C26 | 123.90 (15) | N12—C59—H59E | 109.5 |
O11—C27—C26 | 109.53 (12) | H59A—C59—H59E | 56.3 |
O15—C28—C26 | 107.12 (12) | H59B—C59—H59E | 141.1 |
O15—C28—C29 | 110.14 (12) | H59C—C59—H59E | 56.3 |
C26—C28—C29 | 112.55 (13) | H59D—C59—H59E | 109.5 |
O15—C28—H28 | 109.0 | N12—C59—H59F | 109.5 |
C26—C28—H28 | 109.0 | H59A—C59—H59F | 56.3 |
C29—C28—H28 | 109.0 | H59B—C59—H59F | 56.3 |
O14—C29—O13 | 126.46 (16) | H59C—C59—H59F | 141.1 |
O14—C29—C28 | 123.00 (16) | H59D—C59—H59F | 109.5 |
O13—C29—C28 | 110.49 (13) | H59E—C59—H59F | 109.5 |
O16—C30—O15 | 123.59 (16) | N12—C60—H60A | 109.5 |
O16—C30—C31 | 125.37 (16) | N12—C60—H60B | 109.5 |
O15—C30—C31 | 111.04 (14) | H60A—C60—H60B | 109.5 |
C36—C31—C32 | 120.23 (17) | N12—C60—H60C | 109.5 |
C36—C31—C30 | 117.73 (17) | H60A—C60—H60C | 109.5 |
C32—C31—C30 | 122.00 (15) | H60B—C60—H60C | 109.5 |
C33—C32—C31 | 120.01 (17) | | |
| | | |
O17—P1—N1—C38 | −153.2 (2) | C8—O1—C7—O2 | 1.9 (2) |
N2—P1—N1—C38 | 85.5 (2) | C8—O1—C7—C6 | −179.10 (12) |
N3—P1—N1—C38 | −30.3 (2) | C5—C6—C7—O2 | −1.4 (2) |
O17—P1—N1—C37 | 47.4 (2) | C1—C6—C7—O2 | 177.92 (16) |
N2—P1—N1—C37 | −73.8 (2) | C5—C6—C7—O1 | 179.69 (14) |
N3—P1—N1—C37 | 170.4 (2) | C1—C6—C7—O1 | −1.0 (2) |
O17—P1—N2—C40 | 30.1 (2) | C7—O1—C8—C10 | −159.40 (12) |
N1—P1—N2—C40 | 152.22 (17) | C7—O1—C8—C9 | 78.36 (15) |
N3—P1—N2—C40 | −94.59 (19) | O1—C8—C9—O4 | 175.77 (14) |
O17—P1—N2—C39 | −163.7 (2) | C10—C8—C9—O4 | 55.52 (19) |
N1—P1—N2—C39 | −41.6 (2) | O1—C8—C9—O3 | −5.49 (18) |
N3—P1—N2—C39 | 71.6 (2) | C10—C8—C9—O3 | −125.73 (14) |
O17—P1—N3—C41 | −96.2 (2) | C12—O7—C10—C8 | −159.26 (13) |
N1—P1—N3—C41 | 142.8 (2) | C12—O7—C10—C11 | 77.86 (16) |
N2—P1—N3—C41 | 25.8 (3) | O1—C8—C10—O7 | −65.51 (14) |
O17—P1—N3—C42 | 55.9 (2) | C9—C8—C10—O7 | 58.14 (16) |
N1—P1—N3—C42 | −65.1 (2) | O1—C8—C10—C11 | 55.79 (15) |
N2—P1—N3—C42 | 177.9 (2) | C9—C8—C10—C11 | 179.44 (12) |
O18—P2—N4—C44 | −162.32 (17) | O7—C10—C11—O6 | −5.2 (2) |
N5—P2—N4—C44 | 76.83 (19) | C8—C10—C11—O6 | −125.27 (17) |
N6—P2—N4—C44 | −36.66 (19) | O7—C10—C11—O5 | 176.26 (13) |
O18—P2—N4—C43 | 48.53 (14) | C8—C10—C11—O5 | 56.23 (17) |
N5—P2—N4—C43 | −72.31 (14) | C10—O7—C12—O8 | 3.4 (2) |
N6—P2—N4—C43 | 174.19 (13) | C10—O7—C12—C13 | −177.13 (13) |
O18—P2—N5—C46 | −21.74 (18) | O8—C12—C13—C14 | 179.61 (19) |
N6—P2—N5—C46 | −148.90 (16) | O7—C12—C13—C14 | 0.1 (2) |
N4—P2—N5—C46 | 99.06 (16) | O8—C12—C13—C18 | 0.4 (3) |
O18—P2—N5—C45 | −169.23 (19) | O7—C12—C13—C18 | −179.11 (16) |
N6—P2—N5—C45 | 63.6 (2) | C18—C13—C14—C15 | −0.8 (4) |
N4—P2—N5—C45 | −48.4 (2) | C12—C13—C14—C15 | 179.9 (2) |
O18—P2—N6—C48 | −83.6 (2) | C13—C14—C15—C16 | 1.7 (5) |
N5—P2—N6—C48 | 38.0 (2) | C14—C15—C16—C17 | −1.7 (5) |
N4—P2—N6—C48 | 156.67 (18) | C15—C16—C17—C18 | 0.8 (4) |
O18—P2—N6—C47 | 57.39 (19) | C16—C17—C18—C13 | 0.0 (4) |
N5—P2—N6—C47 | 179.02 (17) | C14—C13—C18—C17 | 0.0 (3) |
N4—P2—N6—C47 | −62.34 (18) | C12—C13—C18—C17 | 179.30 (19) |
O19—P3—N7—C49 | −112.37 (16) | C24—C19—C20—C21 | 1.6 (3) |
N8—P3—N7—C49 | 9.40 (17) | C19—C20—C21—C22 | −0.9 (3) |
N9—P3—N7—C49 | 126.03 (15) | C20—C21—C22—C23 | −0.3 (4) |
O19—P3—N7—C50 | 58.31 (18) | C21—C22—C23—C24 | 0.9 (4) |
N8—P3—N7—C50 | −179.91 (15) | C20—C19—C24—C23 | −0.9 (3) |
N9—P3—N7—C50 | −63.28 (17) | C20—C19—C24—C25 | 178.46 (16) |
O19—P3—N8—C51 | 31.83 (18) | C22—C23—C24—C19 | −0.3 (3) |
N7—P3—N8—C51 | −91.57 (17) | C22—C23—C24—C25 | −179.7 (2) |
N9—P3—N8—C51 | 153.91 (16) | C26—O9—C25—O10 | 4.3 (2) |
O19—P3—N8—C52 | −168.55 (13) | C26—O9—C25—C24 | −176.76 (12) |
N7—P3—N8—C52 | 68.04 (15) | C19—C24—C25—O10 | −162.27 (18) |
N9—P3—N8—C52 | −46.47 (15) | C23—C24—C25—O10 | 17.1 (3) |
O19—P3—N9—C54 | −148.55 (16) | C19—C24—C25—O9 | 18.8 (2) |
N7—P3—N9—C54 | −26.13 (18) | C23—C24—C25—O9 | −161.82 (17) |
N8—P3—N9—C54 | 90.23 (17) | C25—O9—C26—C28 | −136.12 (13) |
O19—P3—N9—C53 | 51.23 (15) | C25—O9—C26—C27 | 101.26 (15) |
N7—P3—N9—C53 | 173.65 (13) | O9—C26—C27—O12 | −10.5 (2) |
N8—P3—N9—C53 | −69.98 (14) | C28—C26—C27—O12 | −130.94 (17) |
O20—P4—N10—C56 | 95.9 (2) | O9—C26—C27—O11 | 171.22 (12) |
N12—P4—N10—C56 | −29.3 (3) | C28—C26—C27—O11 | 50.73 (16) |
N11—P4—N10—C56 | −146.0 (2) | C30—O15—C28—C26 | −159.86 (13) |
O20—P4—N10—C55 | −59.3 (2) | C30—O15—C28—C29 | 77.43 (16) |
N12—P4—N10—C55 | 175.4 (2) | O9—C26—C28—O15 | −58.43 (15) |
N11—P4—N10—C55 | 58.8 (2) | C27—C26—C28—O15 | 62.90 (15) |
O20—P4—N11—C58 | −41.0 (3) | O9—C26—C28—C29 | 62.77 (15) |
N12—P4—N11—C58 | 79.8 (3) | C27—C26—C28—C29 | −175.90 (12) |
N10—P4—N11—C58 | −165.0 (3) | O15—C28—C29—O14 | −13.5 (2) |
O20—P4—N11—C57 | 157.1 (3) | C26—C28—C29—O14 | −132.94 (17) |
N12—P4—N11—C57 | −82.1 (3) | O15—C28—C29—O13 | 168.71 (13) |
N10—P4—N11—C57 | 33.1 (3) | C26—C28—C29—O13 | 49.25 (17) |
O20—P4—N12—C59 | −20.2 (5) | C28—O15—C30—O16 | 6.6 (3) |
N11—P4—N12—C59 | −138.9 (5) | C28—O15—C30—C31 | −173.64 (13) |
N10—P4—N12—C59 | 108.2 (5) | O16—C30—C31—C36 | −3.0 (3) |
O20—P4—N12—C60 | 162.1 (3) | O15—C30—C31—C36 | 177.21 (19) |
N11—P4—N12—C60 | 43.4 (4) | O16—C30—C31—C32 | 179.41 (19) |
N10—P4—N12—C60 | −69.4 (4) | O15—C30—C31—C32 | −0.4 (2) |
C6—C1—C2—C3 | 0.2 (3) | C36—C31—C32—C33 | 0.4 (3) |
C1—C2—C3—C4 | −0.5 (3) | C30—C31—C32—C33 | 177.90 (17) |
C2—C3—C4—C5 | 0.4 (3) | C31—C32—C33—C34 | −0.2 (3) |
C3—C4—C5—C6 | 0.0 (3) | C32—C33—C34—C35 | −0.3 (4) |
C4—C5—C6—C1 | −0.3 (3) | C33—C34—C35—C36 | 0.7 (4) |
C4—C5—C6—C7 | 179.04 (15) | C32—C31—C36—C35 | 0.1 (4) |
C2—C1—C6—C5 | 0.1 (3) | C30—C31—C36—C35 | −177.6 (2) |
C2—C1—C6—C7 | −179.12 (16) | C34—C35—C36—C31 | −0.6 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3O···O19 | 0.82 (1) | 1.68 (1) | 2.4839 (16) | 165 (3) |
O5—H5O···O18 | 0.82 (1) | 1.72 (1) | 2.5262 (16) | 172 (4) |
O11—H11O···O17 | 0.82 (1) | 1.70 (1) | 2.4854 (16) | 160 (3) |
O13—H13O···O20 | 0.82 (1) | 1.70 (2) | 2.4908 (19) | 164 (4) |
C3—H3···O16 | 0.93 | 2.40 | 3.316 (2) | 168 |
C16—H16···O8i | 0.93 | 2.49 | 3.312 (2) | 147 |
C35—H35···O4ii | 0.93 | 2.54 | 3.455 (2) | 168 |
C50—H50C···O18iii | 0.96 | 2.45 | 3.314 (2) | 150 |
Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) −x+1/2, −y, z+1/2; (iii) x−1, y, z. |