Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602469X/hb2095sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680602469X/hb2095Isup2.hkl |
CCDC reference: 610181
Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2002); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2003); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C52H40O12·8C3H7NO | Z = 1 |
Mr = 1441.61 | F(000) = 768 |
Triclinic, P1 | Dx = 1.307 Mg m−3 |
Hall symbol: -P 1 | Melting point: 632 K |
a = 12.199 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.397 (4) Å | Cell parameters from 8495 reflections |
c = 13.712 (4) Å | θ = 2.6–30.6° |
α = 105.282 (5)° | µ = 0.10 mm−1 |
β = 101.099 (5)° | T = 100 K |
γ = 106.854 (5)° | Plate, colourless |
V = 1831.5 (9) Å3 | 0.5 × 0.4 × 0.07 mm |
Bruker SMART APEX CCD diffractometer | 8997 independent reflections |
Radiation source: fine-focus sealed tube | 5924 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
ω scans | θmax = 28.3°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2002) | h = −16→16 |
Tmin = 0.768, Tmax = 1 | k = −16→16 |
18122 measured reflections | l = −18→18 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.169 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0871P)2 + 0.3671P] where P = (Fo2 + 2Fc2)/3 |
8997 reflections | (Δ/σ)max < 0.001 |
501 parameters | Δρmax = 0.48 e Å−3 |
26 restraints | Δρmin = −0.28 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.31161 (14) | −0.04065 (14) | 0.60839 (14) | 0.0333 (4) | |
N1 | 0.25617 (16) | 0.12137 (17) | 0.64951 (15) | 0.0254 (4) | |
C1 | 0.33408 (19) | 0.0673 (2) | 0.65680 (18) | 0.0273 (5) | |
H1 | 0.4129 | 0.1137 | 0.7021 | 0.033* | |
C2 | 0.1351 (2) | 0.0559 (2) | 0.5769 (2) | 0.0339 (6) | |
H2C | 0.1387 | 0.0385 | 0.5038 | 0.051* | |
H2D | 0.0855 | 0.1049 | 0.5891 | 0.051* | |
H2E | 0.1000 | −0.0194 | 0.5891 | 0.051* | |
C3 | 0.2873 (2) | 0.2479 (2) | 0.70856 (19) | 0.0289 (5) | |
H3C | 0.3732 | 0.2839 | 0.7456 | 0.043* | |
H3D | 0.2419 | 0.2557 | 0.7601 | 0.043* | |
H3E | 0.2676 | 0.2892 | 0.6596 | 0.043* | |
O2 | 0.3715 (3) | 0.2357 (4) | 0.4735 (4) | 0.0340 (8) | 0.863 (3) |
C4 | 0.3017 (3) | 0.2879 (3) | 0.4568 (2) | 0.0286 (6) | 0.863 (3) |
H4 | 0.2300 | 0.2649 | 0.4762 | 0.034* | 0.863 (3) |
N2 | 0.3185 (2) | 0.3742 (2) | 0.41351 (19) | 0.0303 (6) | 0.863 (3) |
C5 | 0.2340 (3) | 0.4366 (3) | 0.4046 (3) | 0.0385 (8) | 0.863 (3) |
H5C | 0.1650 | 0.3985 | 0.4263 | 0.058* | 0.863 (3) |
H5D | 0.2069 | 0.4324 | 0.3312 | 0.058* | 0.863 (3) |
H5E | 0.2735 | 0.5207 | 0.4504 | 0.058* | 0.863 (3) |
C6 | 0.4232 (3) | 0.4124 (3) | 0.3775 (3) | 0.0414 (8) | 0.863 (3) |
H6A | 0.4823 | 0.3801 | 0.4046 | 0.062* | 0.863 (3) |
H6B | 0.4584 | 0.5001 | 0.4035 | 0.062* | 0.863 (3) |
H6C | 0.3995 | 0.3826 | 0.3000 | 0.062* | 0.863 (3) |
O2C | 0.346 (3) | 0.226 (3) | 0.483 (3) | 0.0340 (8) | 0.137 (3) |
C4C | 0.3427 (17) | 0.2992 (18) | 0.4379 (17) | 0.0286 (6) | 0.137 (3) |
H4C | 0.4020 | 0.3192 | 0.4033 | 0.034* | 0.137 (3) |
N2C | 0.2618 (13) | 0.3525 (13) | 0.4335 (12) | 0.0303 (6) | 0.137 (3) |
C5C | 0.278 (2) | 0.453 (2) | 0.396 (2) | 0.0385 (8) | 0.137 (3) |
H5C1 | 0.3564 | 0.4762 | 0.3839 | 0.058* | 0.137 (3) |
H5C2 | 0.2731 | 0.5202 | 0.4498 | 0.058* | 0.137 (3) |
H5C3 | 0.2149 | 0.4300 | 0.3304 | 0.058* | 0.137 (3) |
C6C | 0.1593 (14) | 0.3203 (18) | 0.4742 (15) | 0.0414 (8) | 0.137 (3) |
H6C1 | 0.1419 | 0.2387 | 0.4763 | 0.062* | 0.137 (3) |
H6C2 | 0.0894 | 0.3239 | 0.4280 | 0.062* | 0.137 (3) |
H6C3 | 0.1779 | 0.3765 | 0.5457 | 0.062* | 0.137 (3) |
O3 | 0.74920 (14) | 0.90029 (14) | 0.89433 (13) | 0.0282 (4) | |
N3 | 0.67255 (15) | 0.96148 (16) | 0.76250 (14) | 0.0227 (4) | |
C7 | 0.76129 (19) | 0.96283 (19) | 0.83541 (17) | 0.0230 (4) | |
H7 | 0.8398 | 1.0146 | 0.8441 | 0.028* | |
C8 | 0.54917 (19) | 0.8842 (2) | 0.74269 (19) | 0.0297 (5) | |
H8A | 0.5196 | 0.8268 | 0.6704 | 0.045* | |
H8B | 0.4991 | 0.9332 | 0.7514 | 0.045* | |
H8C | 0.5458 | 0.8408 | 0.7930 | 0.045* | |
C9 | 0.6923 (2) | 1.0345 (2) | 0.69487 (19) | 0.0297 (5) | |
H9A | 0.7775 | 1.0835 | 0.7154 | 0.045* | |
H9B | 0.6456 | 1.0869 | 0.7029 | 0.045* | |
H9C | 0.6670 | 0.9821 | 0.6210 | 0.045* | |
O4 | −0.02849 (16) | 0.91253 (15) | 0.72569 (14) | 0.0369 (4) | |
N4 | 0.08930 (17) | 0.84605 (17) | 0.82835 (16) | 0.0279 (4) | |
C10 | −0.0153 (2) | 0.8451 (2) | 0.77530 (19) | 0.0292 (5) | |
H10 | −0.0858 | 0.7872 | 0.7758 | 0.035* | |
C11 | 0.2020 (2) | 0.9313 (2) | 0.8325 (2) | 0.0362 (6) | |
H11A | 0.1864 | 0.9800 | 0.7895 | 0.054* | |
H11B | 0.2513 | 0.8879 | 0.8050 | 0.054* | |
H11C | 0.2444 | 0.9834 | 0.9059 | 0.054* | |
C12 | 0.0940 (2) | 0.7637 (2) | 0.8862 (2) | 0.0334 (5) | |
H12A | 0.1253 | 0.8087 | 0.9622 | 0.050* | |
H12B | 0.1466 | 0.7213 | 0.8648 | 0.050* | |
H12C | 0.0133 | 0.7055 | 0.8705 | 0.050* | |
C1A | 0.66115 (19) | 0.25181 (19) | 0.91647 (17) | 0.0243 (4) | |
H1A1 | 0.7288 | 0.2446 | 0.8946 | 0.029* | |
C2A | 0.5985 (2) | 0.1667 (2) | 0.95465 (19) | 0.0306 (5) | |
H2A1 | 0.6243 | 0.1024 | 0.9593 | 0.037* | |
C3A | 0.4998 (2) | 0.1754 (2) | 0.98562 (19) | 0.0345 (6) | |
H3A1 | 0.4573 | 0.1171 | 1.0113 | 0.041* | |
C4A | 0.4623 (2) | 0.2699 (2) | 0.9792 (2) | 0.0378 (6) | |
H4A | 0.3942 | 0.2763 | 1.0006 | 0.045* | |
C5A | 0.52493 (19) | 0.3549 (2) | 0.94137 (19) | 0.0296 (5) | |
H5A | 0.4987 | 0.4189 | 0.9368 | 0.035* | |
C6A | 0.62514 (17) | 0.34758 (19) | 0.91011 (16) | 0.0204 (4) | |
C7A | 0.69330 (17) | 0.44472 (17) | 0.87167 (16) | 0.0177 (4) | |
H7A | 0.6328 | 0.4737 | 0.8378 | 0.021* | |
C8A | 0.74507 (17) | 0.39330 (17) | 0.78589 (16) | 0.0169 (4) | |
C9A | 0.66703 (16) | 0.32301 (17) | 0.68478 (16) | 0.0172 (4) | |
C10A | 0.70693 (17) | 0.26725 (17) | 0.60476 (16) | 0.0179 (4) | |
C11A | 0.82808 (17) | 0.28056 (17) | 0.62340 (15) | 0.0165 (4) | |
C12A | 0.90828 (16) | 0.35043 (17) | 0.72367 (16) | 0.0168 (4) | |
C13A | 0.86555 (17) | 0.40571 (17) | 0.80272 (16) | 0.0171 (4) | |
H13A | 0.9204 | 0.4535 | 0.8705 | 0.021* | |
C1B | 1.23977 (18) | 0.51700 (19) | 0.75398 (17) | 0.0219 (4) | |
H1B1 | 1.2799 | 0.4829 | 0.7968 | 0.026* | |
C2B | 1.3062 (2) | 0.6099 (2) | 0.72625 (18) | 0.0276 (5) | |
H2B1 | 1.3912 | 0.6391 | 0.7510 | 0.033* | |
C3B | 1.2499 (2) | 0.6601 (2) | 0.66308 (19) | 0.0299 (5) | |
H3B1 | 1.2957 | 0.7234 | 0.6443 | 0.036* | |
C4B | 1.1258 (2) | 0.6171 (2) | 0.62755 (19) | 0.0288 (5) | |
H4B | 1.0863 | 0.6507 | 0.5838 | 0.035* | |
C5B | 1.05914 (19) | 0.5250 (2) | 0.65568 (18) | 0.0244 (5) | |
H5B | 0.9742 | 0.4966 | 0.6310 | 0.029* | |
C6B | 1.11444 (17) | 0.47313 (18) | 0.71952 (16) | 0.0186 (4) | |
C7B | 1.04044 (16) | 0.36534 (17) | 0.74297 (15) | 0.0165 (4) | |
H7B | 1.0418 | 0.2932 | 0.6898 | 0.020* | |
C8B | 1.09230 (16) | 0.35832 (17) | 0.85051 (15) | 0.0164 (4) | |
C9B | 1.06900 (16) | 0.24441 (17) | 0.85955 (16) | 0.0176 (4) | |
C10B | 1.11424 (17) | 0.23081 (18) | 0.95522 (17) | 0.0190 (4) | |
C11B | 1.18962 (17) | 0.33193 (18) | 1.04200 (16) | 0.0190 (4) | |
C12B | 1.21629 (17) | 0.44726 (18) | 1.03517 (16) | 0.0179 (4) | |
C13B | 1.16358 (17) | 0.45734 (18) | 0.93973 (16) | 0.0180 (4) | |
H13B | 1.1769 | 0.5352 | 0.9355 | 0.022* | |
O1A | 0.54856 (12) | 0.30995 (14) | 0.66641 (12) | 0.0223 (3) | |
H1A | 0.5127 | 0.2738 | 0.6018 | 0.033* | |
O2A | 0.62121 (12) | 0.20383 (14) | 0.50824 (11) | 0.0232 (3) | |
H2A | 0.6411 | 0.1496 | 0.4738 | 0.035* | |
O3A | 0.87216 (12) | 0.22918 (13) | 0.54627 (11) | 0.0216 (3) | |
H3A | 0.8160 | 0.1714 | 0.4986 | 0.032* | |
O1B | 1.00058 (13) | 0.14664 (13) | 0.77173 (12) | 0.0223 (3) | |
H1B | 1.0080 | 0.0846 | 0.7814 | 0.033* | |
O2B | 1.07824 (13) | 0.11569 (13) | 0.95740 (12) | 0.0254 (3) | |
H2B | 1.1297 | 0.1102 | 1.0044 | 0.038* | |
O3B | 1.23926 (14) | 0.32294 (14) | 1.13777 (11) | 0.0248 (3) | |
H3B | 1.2480 | 0.2565 | 1.1273 | 0.037* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0238 (8) | 0.0261 (9) | 0.0415 (10) | 0.0084 (7) | 0.0040 (7) | 0.0026 (7) |
N1 | 0.0164 (8) | 0.0255 (10) | 0.0289 (10) | 0.0052 (7) | 0.0048 (7) | 0.0048 (8) |
C1 | 0.0174 (10) | 0.0273 (12) | 0.0315 (12) | 0.0054 (9) | 0.0065 (9) | 0.0046 (9) |
C2 | 0.0197 (11) | 0.0335 (13) | 0.0387 (13) | 0.0081 (10) | 0.0004 (10) | 0.0044 (11) |
C3 | 0.0229 (11) | 0.0270 (12) | 0.0345 (13) | 0.0079 (9) | 0.0100 (10) | 0.0068 (10) |
O2 | 0.032 (2) | 0.0377 (13) | 0.0331 (15) | 0.0185 (16) | 0.0002 (13) | 0.0127 (9) |
C4 | 0.0236 (16) | 0.0346 (14) | 0.0288 (15) | 0.0113 (13) | 0.0057 (11) | 0.0133 (11) |
N2 | 0.0261 (13) | 0.0292 (12) | 0.0349 (13) | 0.0098 (11) | 0.0047 (10) | 0.0130 (10) |
C5 | 0.042 (2) | 0.0393 (17) | 0.0422 (17) | 0.0238 (18) | 0.0086 (18) | 0.0183 (13) |
C6 | 0.0291 (15) | 0.0458 (18) | 0.0372 (16) | 0.0013 (13) | 0.0001 (12) | 0.0155 (14) |
O2C | 0.032 (2) | 0.0377 (13) | 0.0331 (15) | 0.0185 (16) | 0.0002 (13) | 0.0127 (9) |
C4C | 0.0236 (16) | 0.0346 (14) | 0.0288 (15) | 0.0113 (13) | 0.0057 (11) | 0.0133 (11) |
N2C | 0.0261 (13) | 0.0292 (12) | 0.0349 (13) | 0.0098 (11) | 0.0047 (10) | 0.0130 (10) |
C5C | 0.042 (2) | 0.0393 (17) | 0.0422 (17) | 0.0238 (18) | 0.0086 (18) | 0.0183 (13) |
C6C | 0.0291 (15) | 0.0458 (18) | 0.0372 (16) | 0.0013 (13) | 0.0001 (12) | 0.0155 (14) |
O3 | 0.0260 (8) | 0.0304 (8) | 0.0328 (9) | 0.0112 (7) | 0.0058 (7) | 0.0190 (7) |
N3 | 0.0176 (8) | 0.0233 (9) | 0.0283 (9) | 0.0055 (7) | 0.0047 (7) | 0.0141 (8) |
C7 | 0.0171 (10) | 0.0237 (11) | 0.0288 (11) | 0.0067 (8) | 0.0052 (8) | 0.0117 (9) |
C8 | 0.0184 (10) | 0.0338 (13) | 0.0349 (13) | 0.0040 (9) | 0.0039 (9) | 0.0172 (10) |
C9 | 0.0291 (12) | 0.0292 (12) | 0.0350 (13) | 0.0090 (10) | 0.0079 (10) | 0.0201 (10) |
O4 | 0.0376 (10) | 0.0250 (9) | 0.0453 (10) | 0.0112 (7) | 0.0043 (8) | 0.0133 (8) |
N4 | 0.0237 (9) | 0.0256 (10) | 0.0374 (11) | 0.0089 (8) | 0.0103 (8) | 0.0147 (8) |
C10 | 0.0255 (11) | 0.0216 (11) | 0.0384 (13) | 0.0076 (9) | 0.0073 (10) | 0.0095 (10) |
C11 | 0.0234 (11) | 0.0357 (14) | 0.0488 (15) | 0.0068 (10) | 0.0121 (11) | 0.0163 (12) |
C12 | 0.0345 (13) | 0.0324 (13) | 0.0397 (14) | 0.0155 (11) | 0.0118 (11) | 0.0178 (11) |
C1A | 0.0184 (10) | 0.0257 (11) | 0.0270 (11) | 0.0043 (8) | 0.0065 (8) | 0.0103 (9) |
C2A | 0.0290 (12) | 0.0269 (12) | 0.0319 (12) | 0.0028 (10) | 0.0063 (10) | 0.0135 (10) |
C3A | 0.0273 (12) | 0.0354 (13) | 0.0306 (13) | −0.0048 (10) | 0.0088 (10) | 0.0128 (10) |
C4A | 0.0221 (11) | 0.0454 (15) | 0.0407 (14) | 0.0019 (11) | 0.0175 (11) | 0.0117 (12) |
C5A | 0.0192 (11) | 0.0319 (12) | 0.0354 (13) | 0.0073 (9) | 0.0103 (9) | 0.0085 (10) |
C6A | 0.0125 (9) | 0.0240 (10) | 0.0196 (10) | 0.0014 (8) | 0.0028 (7) | 0.0061 (8) |
C7A | 0.0134 (9) | 0.0186 (10) | 0.0207 (10) | 0.0060 (7) | 0.0038 (7) | 0.0066 (8) |
C8A | 0.0148 (9) | 0.0158 (9) | 0.0217 (10) | 0.0053 (7) | 0.0057 (8) | 0.0088 (8) |
C9A | 0.0108 (9) | 0.0184 (10) | 0.0238 (10) | 0.0039 (7) | 0.0046 (7) | 0.0112 (8) |
C10A | 0.0147 (9) | 0.0169 (9) | 0.0207 (10) | 0.0028 (7) | 0.0025 (7) | 0.0092 (8) |
C11A | 0.0143 (9) | 0.0161 (9) | 0.0207 (10) | 0.0037 (7) | 0.0057 (7) | 0.0105 (8) |
C12A | 0.0122 (9) | 0.0175 (9) | 0.0230 (10) | 0.0040 (7) | 0.0050 (7) | 0.0118 (8) |
C13A | 0.0127 (9) | 0.0164 (9) | 0.0205 (10) | 0.0023 (7) | 0.0029 (7) | 0.0081 (8) |
C1B | 0.0160 (10) | 0.0229 (11) | 0.0282 (11) | 0.0061 (8) | 0.0072 (8) | 0.0112 (9) |
C2B | 0.0181 (10) | 0.0285 (12) | 0.0336 (12) | 0.0020 (9) | 0.0093 (9) | 0.0123 (10) |
C3B | 0.0281 (12) | 0.0278 (12) | 0.0332 (12) | 0.0024 (9) | 0.0120 (10) | 0.0160 (10) |
C4B | 0.0275 (11) | 0.0281 (12) | 0.0333 (12) | 0.0068 (9) | 0.0068 (10) | 0.0195 (10) |
C5B | 0.0176 (10) | 0.0272 (11) | 0.0300 (11) | 0.0054 (8) | 0.0065 (8) | 0.0158 (9) |
C6B | 0.0155 (9) | 0.0195 (10) | 0.0231 (10) | 0.0054 (8) | 0.0087 (8) | 0.0094 (8) |
C7B | 0.0125 (9) | 0.0169 (9) | 0.0204 (9) | 0.0040 (7) | 0.0033 (7) | 0.0094 (8) |
C8B | 0.0104 (8) | 0.0199 (10) | 0.0218 (10) | 0.0064 (7) | 0.0055 (7) | 0.0102 (8) |
C9B | 0.0099 (8) | 0.0182 (10) | 0.0250 (10) | 0.0042 (7) | 0.0053 (7) | 0.0084 (8) |
C10B | 0.0138 (9) | 0.0182 (10) | 0.0279 (11) | 0.0059 (8) | 0.0071 (8) | 0.0114 (8) |
C11B | 0.0132 (9) | 0.0246 (10) | 0.0226 (10) | 0.0080 (8) | 0.0054 (8) | 0.0119 (8) |
C12B | 0.0122 (9) | 0.0200 (10) | 0.0223 (10) | 0.0063 (7) | 0.0058 (8) | 0.0073 (8) |
C13B | 0.0135 (9) | 0.0187 (10) | 0.0251 (10) | 0.0069 (7) | 0.0075 (8) | 0.0102 (8) |
O1A | 0.0111 (6) | 0.0296 (8) | 0.0230 (7) | 0.0059 (6) | 0.0020 (5) | 0.0077 (6) |
O2A | 0.0161 (7) | 0.0278 (8) | 0.0211 (7) | 0.0075 (6) | 0.0016 (6) | 0.0044 (6) |
O3A | 0.0159 (7) | 0.0246 (8) | 0.0215 (7) | 0.0050 (6) | 0.0055 (6) | 0.0058 (6) |
O1B | 0.0191 (7) | 0.0167 (7) | 0.0279 (8) | 0.0035 (6) | 0.0014 (6) | 0.0099 (6) |
O2B | 0.0227 (8) | 0.0205 (7) | 0.0314 (9) | 0.0045 (6) | 0.0011 (6) | 0.0146 (7) |
O3B | 0.0249 (8) | 0.0259 (8) | 0.0244 (8) | 0.0091 (7) | 0.0023 (6) | 0.0136 (6) |
O1—C1 | 1.248 (3) | C1A—C6A | 1.397 (3) |
N1—C1 | 1.315 (3) | C1A—H1A1 | 0.9500 |
N1—C3 | 1.459 (3) | C2A—C3A | 1.375 (4) |
N1—C2 | 1.465 (3) | C2A—H2A1 | 0.9500 |
C1—H1 | 0.9500 | C3A—C4A | 1.392 (4) |
C2—H2C | 0.9800 | C3A—H3A1 | 0.9500 |
C2—H2D | 0.9800 | C4A—C5A | 1.392 (3) |
C2—H2E | 0.9800 | C4A—H4A | 0.9500 |
C3—H3C | 0.9800 | C5A—C6A | 1.390 (3) |
C3—H3D | 0.9800 | C5A—H5A | 0.9500 |
C3—H3E | 0.9800 | C6A—C7A | 1.530 (3) |
O2—C4 | 1.232 (4) | C7A—C8A | 1.521 (3) |
C4—N2 | 1.339 (3) | C7A—C12Bi | 1.530 (3) |
C4—H4 | 0.9500 | C7A—H7A | 1.0000 |
N2—C6 | 1.455 (4) | C8A—C13A | 1.399 (3) |
N2—C5 | 1.463 (4) | C8A—C9A | 1.401 (3) |
C5—H5C | 0.9800 | C9A—O1A | 1.372 (2) |
C5—H5D | 0.9800 | C9A—C10A | 1.385 (3) |
C5—H5E | 0.9800 | C10A—O2A | 1.380 (2) |
C6—H6A | 0.9800 | C10A—C11A | 1.403 (3) |
C6—H6B | 0.9800 | C11A—O3A | 1.370 (2) |
C6—H6C | 0.9800 | C11A—C12A | 1.400 (3) |
O2C—C4C | 1.234 (17) | C12A—C13A | 1.396 (3) |
C4C—N2C | 1.338 (15) | C12A—C7B | 1.530 (3) |
C4C—H4C | 0.9500 | C13A—H13A | 0.9500 |
N2C—C5C | 1.438 (16) | C1B—C2B | 1.391 (3) |
N2C—C6C | 1.459 (15) | C1B—C6B | 1.400 (3) |
C5C—H5C1 | 0.9800 | C1B—H1B1 | 0.9500 |
C5C—H5C2 | 0.9800 | C2B—C3B | 1.384 (3) |
C5C—H5C3 | 0.9800 | C2B—H2B1 | 0.9500 |
C6C—H6C1 | 0.9800 | C3B—C4B | 1.387 (3) |
C6C—H6C2 | 0.9800 | C3B—H3B1 | 0.9500 |
C6C—H6C3 | 0.9800 | C4B—C5B | 1.389 (3) |
O3—C7 | 1.259 (3) | C4B—H4B | 0.9500 |
N3—C7 | 1.317 (3) | C5B—C6B | 1.398 (3) |
N3—C8 | 1.458 (3) | C5B—H5B | 0.9500 |
N3—C9 | 1.463 (3) | C6B—C7B | 1.531 (3) |
C7—H7 | 0.9500 | C7B—C8B | 1.524 (3) |
C8—H8A | 0.9800 | C7B—H7B | 1.0000 |
C8—H8B | 0.9800 | C8B—C13B | 1.393 (3) |
C8—H8C | 0.9800 | C8B—C9B | 1.401 (3) |
C9—H9A | 0.9800 | C9B—O1B | 1.369 (2) |
C9—H9B | 0.9800 | C9B—C10B | 1.395 (3) |
C9—H9C | 0.9800 | C10B—O2B | 1.377 (2) |
O4—C10 | 1.235 (3) | C10B—C11B | 1.399 (3) |
N4—C10 | 1.336 (3) | C11B—O3B | 1.383 (2) |
N4—C11 | 1.451 (3) | C11B—C12B | 1.404 (3) |
N4—C12 | 1.456 (3) | C12B—C13B | 1.397 (3) |
C10—H10 | 0.9500 | C12B—C7Ai | 1.530 (3) |
C11—H11A | 0.9800 | C13B—H13B | 0.9500 |
C11—H11B | 0.9800 | O1A—H1A | 0.8400 |
C11—H11C | 0.9800 | O2A—H2A | 0.8400 |
C12—H12A | 0.9800 | O3A—H3A | 0.8400 |
C12—H12B | 0.9800 | O1B—H1B | 0.8400 |
C12—H12C | 0.9800 | O2B—H2B | 0.8400 |
C1A—C2A | 1.396 (3) | O3B—H3B | 0.8400 |
C1—N1—C3 | 122.19 (19) | C5A—C6A—C1A | 118.4 (2) |
C1—N1—C2 | 120.15 (19) | C5A—C6A—C7A | 119.42 (19) |
C3—N1—C2 | 117.61 (18) | C1A—C6A—C7A | 122.20 (18) |
O1—C1—N1 | 124.5 (2) | C8A—C7A—C12Bi | 114.82 (16) |
O1—C1—H1 | 117.7 | C8A—C7A—C6A | 111.36 (16) |
N1—C1—H1 | 117.7 | C12Bi—C7A—C6A | 110.94 (16) |
N1—C2—H2C | 109.5 | C8A—C7A—H7A | 106.4 |
N1—C2—H2D | 109.5 | C12Bi—C7A—H7A | 106.4 |
H2C—C2—H2D | 109.5 | C6A—C7A—H7A | 106.4 |
N1—C2—H2E | 109.5 | C13A—C8A—C9A | 117.21 (18) |
H2C—C2—H2E | 109.5 | C13A—C8A—C7A | 124.12 (17) |
H2D—C2—H2E | 109.5 | C9A—C8A—C7A | 118.56 (17) |
N1—C3—H3C | 109.5 | O1A—C9A—C10A | 120.22 (17) |
N1—C3—H3D | 109.5 | O1A—C9A—C8A | 118.19 (17) |
H3C—C3—H3D | 109.5 | C10A—C9A—C8A | 121.59 (17) |
N1—C3—H3E | 109.5 | O2A—C10A—C9A | 115.48 (17) |
H3C—C3—H3E | 109.5 | O2A—C10A—C11A | 124.19 (18) |
H3D—C3—H3E | 109.5 | C9A—C10A—C11A | 120.29 (18) |
O2—C4—N2 | 125.5 (3) | O3A—C11A—C12A | 118.16 (16) |
O2—C4—H4 | 117.3 | O3A—C11A—C10A | 122.41 (17) |
N2—C4—H4 | 117.3 | C12A—C11A—C10A | 119.42 (18) |
C4—N2—C6 | 121.4 (3) | C13A—C12A—C11A | 119.02 (17) |
C4—N2—C5 | 120.9 (3) | C13A—C12A—C7B | 121.93 (17) |
C6—N2—C5 | 117.6 (3) | C11A—C12A—C7B | 119.04 (17) |
O2C—C4C—N2C | 125 (2) | C12A—C13A—C8A | 122.47 (18) |
O2C—C4C—H4C | 117.5 | C12A—C13A—H13A | 118.8 |
N2C—C4C—H4C | 117.5 | C8A—C13A—H13A | 118.8 |
C4C—N2C—C5C | 121.0 (16) | C2B—C1B—C6B | 120.78 (19) |
C4C—N2C—C6C | 122.5 (14) | C2B—C1B—H1B1 | 119.6 |
C5C—N2C—C6C | 116.3 (15) | C6B—C1B—H1B1 | 119.6 |
N2C—C5C—H5C1 | 109.5 | C3B—C2B—C1B | 120.7 (2) |
N2C—C5C—H5C2 | 109.5 | C3B—C2B—H2B1 | 119.7 |
H5C1—C5C—H5C2 | 109.5 | C1B—C2B—H2B1 | 119.7 |
N2C—C5C—H5C3 | 109.5 | C2B—C3B—C4B | 119.3 (2) |
H5C1—C5C—H5C3 | 109.5 | C2B—C3B—H3B1 | 120.4 |
H5C2—C5C—H5C3 | 109.5 | C4B—C3B—H3B1 | 120.4 |
N2C—C6C—H6C1 | 109.5 | C3B—C4B—C5B | 120.2 (2) |
N2C—C6C—H6C2 | 109.5 | C3B—C4B—H4B | 119.9 |
H6C1—C6C—H6C2 | 109.5 | C5B—C4B—H4B | 119.9 |
N2C—C6C—H6C3 | 109.5 | C4B—C5B—C6B | 121.3 (2) |
H6C1—C6C—H6C3 | 109.5 | C4B—C5B—H5B | 119.3 |
H6C2—C6C—H6C3 | 109.5 | C6B—C5B—H5B | 119.3 |
C7—N3—C8 | 121.69 (18) | C5B—C6B—C1B | 117.68 (18) |
C7—N3—C9 | 122.10 (18) | C5B—C6B—C7B | 120.86 (17) |
C8—N3—C9 | 116.18 (17) | C1B—C6B—C7B | 121.26 (17) |
O3—C7—N3 | 124.5 (2) | C8B—C7B—C12A | 111.25 (16) |
O3—C7—H7 | 117.7 | C8B—C7B—C6B | 114.99 (16) |
N3—C7—H7 | 117.7 | C12A—C7B—C6B | 113.15 (15) |
C10—N4—C11 | 121.2 (2) | C8B—C7B—H7B | 105.5 |
C10—N4—C12 | 121.1 (2) | C12A—C7B—H7B | 105.5 |
C11—N4—C12 | 117.7 (2) | C6B—C7B—H7B | 105.5 |
O4—C10—N4 | 125.9 (2) | C13B—C8B—C9B | 117.82 (17) |
O4—C10—H10 | 117.0 | C13B—C8B—C7B | 124.39 (17) |
N4—C10—H10 | 117.0 | C9B—C8B—C7B | 117.77 (17) |
C2A—C1A—C6A | 120.5 (2) | O1B—C9B—C10B | 120.84 (18) |
C2A—C1A—H1A1 | 119.7 | O1B—C9B—C8B | 118.11 (17) |
C6A—C1A—H1A1 | 119.7 | C10B—C9B—C8B | 121.05 (18) |
C3A—C2A—C1A | 120.4 (2) | O2B—C10B—C9B | 116.17 (18) |
C3A—C2A—H2A1 | 119.8 | O2B—C10B—C11B | 124.26 (18) |
C1A—C2A—H2A1 | 119.8 | C9B—C10B—C11B | 119.55 (18) |
C2A—C3A—C4A | 119.8 (2) | O3B—C11B—C10B | 121.78 (18) |
C2A—C3A—H3A1 | 120.1 | O3B—C11B—C12B | 117.43 (18) |
C4A—C3A—H3A1 | 120.1 | C10B—C11B—C12B | 120.78 (18) |
C3A—C4A—C5A | 119.8 (2) | C13B—C12B—C11B | 117.77 (18) |
C3A—C4A—H4A | 120.1 | C13B—C12B—C7Ai | 122.50 (18) |
C5A—C4A—H4A | 120.1 | C11B—C12B—C7Ai | 119.62 (17) |
C6A—C5A—C4A | 121.1 (2) | C8B—C13B—C12B | 122.87 (18) |
C6A—C5A—H5A | 119.4 | C8B—C13B—H13B | 118.6 |
C4A—C5A—H5A | 119.4 | C12B—C13B—H13B | 118.6 |
Symmetry code: (i) −x+2, −y+1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O2 | 0.84 | 2.05 | 2.805 (5) | 149 |
O1A—H1A···O2A | 0.84 | 2.21 | 2.671 (2) | 115 |
O2A—H2A···O1ii | 0.84 | 1.82 | 2.661 (2) | 175 |
O3A—H3A···O1ii | 0.84 | 1.90 | 2.739 (2) | 180 |
O1B—H1B···O4iii | 0.84 | 1.95 | 2.702 (2) | 149 |
O1B—H1B···O2B | 0.84 | 2.29 | 2.706 (2) | 111 |
O2B—H2B···O3i | 0.84 | 1.88 | 2.722 (2) | 177 |
O3B—H3B···O3i | 0.84 | 1.90 | 2.735 (2) | 174 |
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+1, −y, −z+1; (iii) x+1, y−1, z. |