Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680201872X/bt6201sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680201872X/bt62014sup2.hkl |
CCDC reference: 155873
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.004 Å
- R factor = 0.045
- wR factor = 0.111
- Data-to-parameter ratio = 18.6
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(3) - C(12) = 1.44 Ang. PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 31 C4 -C3 -C12 -N13 126.00 12.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 32 C2 -C3 -C12 -N13 -53.00 12.00 1.555 1.555 1.555 1.555 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 7289 Count of symmetry unique reflns 4155 Completeness (_total/calc) 175.43% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3134 Fraction of Friedel pairs measured 0.754 Are heavy atom types Z>Si present yes 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.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check
Data collection: XSCANS (Fait, 1991); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.
C30H33N3O9S | Dx = 1.281 Mg m−3 |
Mr = 611.65 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 61 reflections |
a = 8.0237 (14) Å | θ = 4.5–12.5° |
b = 10.2293 (14) Å | µ = 0.16 mm−1 |
c = 38.636 (6) Å | T = 173 K |
V = 3171.1 (9) Å3 | Tablet, colourless |
Z = 4 | 0.60 × 0.45 × 0.25 mm |
F(000) = 1288 |
Siemens P4 diffractometer | Rint = 0.022 |
Radiation source: fine-focus sealed tube | θmax = 27.5°, θmin = 3.2° |
Graphite monochromator | h = −10→10 |
ω–scans | k = −13→0 |
7824 measured reflections | l = 0→50 |
7289 independent reflections | 3 standard reflections every 247 reflections |
5529 reflections with I > 2σ(I) | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.111 | w = 1/[σ2(Fo2) + (0.0643P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max = 0.018 |
7289 reflections | Δρmax = 0.43 e Å−3 |
392 parameters | Δρmin = −0.28 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.09 (8) |
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 2.3626 (0.0187) x + 5.2939 (0.0127) y + 31.0403 (0.0432) z = 28.5469 (0.0330) * -0.0107 (0.0009) C5 * 0.0109 (0.0009) C9 * -0.0229 (0.0019) C10 * 0.0227 (0.0019) C11 - 1.2242 (0.0061) C6 - 1.2060 (0.0073) C7 - 1.1798 (0.0060) C8 Rms deviation of fitted atoms = 0.0178 - 2.3734 (0.0457) x + 5.4440 (0.0190) y + 30.6484 (0.0889) z = 27.1271 (0.0634) Angle to previous plane (with approximate e.s.d.) = 1.02 (0.42) * 0.0000 (0.0000) C6 * 0.0000 (0.0000) C7 * 0.0000 (0.0000) C8 Rms deviation of fitted atoms = 0.0000 |
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 | ||
S | 0.60092 (7) | 0.49702 (6) | 0.878323 (16) | 0.03099 (13) | |
O1 | 0.37769 (19) | 0.42109 (14) | 0.92324 (4) | 0.0277 (3) | |
O2 | 0.64631 (18) | 0.18940 (15) | 0.87778 (4) | 0.0304 (4) | |
O3 | 0.5351 (2) | 0.04489 (14) | 0.93768 (4) | 0.0304 (4) | |
O4 | 0.2138 (2) | 0.11383 (15) | 0.95799 (4) | 0.0341 (4) | |
O5 | 0.0610 (2) | 0.51253 (18) | 0.93864 (5) | 0.0414 (4) | |
O6 | 0.8998 (3) | 0.2544 (3) | 0.89351 (7) | 0.0785 (8) | |
O7 | 0.4022 (3) | −0.09843 (16) | 0.90312 (4) | 0.0432 (4) | |
O8 | 0.2244 (3) | 0.1743 (2) | 1.01388 (5) | 0.0497 (5) | |
O9 | 0.2129 (3) | 0.66015 (19) | 0.96802 (5) | 0.0523 (5) | |
N1 | 0.2985 (3) | 0.52590 (19) | 0.84962 (6) | 0.0386 (5) | |
C2 | 0.4462 (3) | 0.5818 (2) | 0.85412 (6) | 0.0297 (5) | |
C3 | 0.4818 (3) | 0.7062 (2) | 0.84100 (6) | 0.0266 (5) | |
C4 | 0.3653 (3) | 0.7689 (2) | 0.82020 (6) | 0.0331 (5) | |
C5 | 0.0740 (4) | 0.7722 (3) | 0.79327 (9) | 0.0528 (8) | |
H5A | −0.0228 | 0.7914 | 0.8083 | 0.063* | |
H5B | 0.1161 | 0.8566 | 0.7843 | 0.063* | |
C6 | 0.0156 (5) | 0.6917 (4) | 0.76345 (9) | 0.0723 (10) | |
H6A | 0.1137 | 0.6502 | 0.7525 | 0.087* | |
H6B | −0.0356 | 0.7505 | 0.7461 | 0.087* | |
C7 | −0.1100 (5) | 0.5851 (3) | 0.77267 (9) | 0.0672 (9) | |
H7A | −0.2078 | 0.6266 | 0.7838 | 0.081* | |
H7B | −0.1489 | 0.5435 | 0.7510 | 0.081* | |
C8 | −0.0437 (4) | 0.4786 (3) | 0.79671 (10) | 0.0707 (10) | |
H8A | −0.1322 | 0.4122 | 0.8000 | 0.085* | |
H8B | 0.0514 | 0.4350 | 0.7852 | 0.085* | |
C9 | 0.0117 (3) | 0.5247 (3) | 0.83142 (9) | 0.0523 (8) | |
H9A | 0.0150 | 0.4488 | 0.8473 | 0.063* | |
H9B | −0.0724 | 0.5867 | 0.8405 | 0.063* | |
C10 | 0.1800 (3) | 0.5906 (3) | 0.83190 (7) | 0.0407 (6) | |
C11 | 0.2089 (3) | 0.7105 (3) | 0.81512 (7) | 0.0403 (6) | |
C12 | 0.6375 (3) | 0.7688 (2) | 0.84973 (6) | 0.0310 (5) | |
N13 | 0.7596 (3) | 0.8178 (2) | 0.85719 (7) | 0.0454 (6) | |
C14 | 0.4056 (3) | 0.9003 (2) | 0.80537 (6) | 0.0328 (5) | |
C15 | 0.4877 (4) | 0.9112 (3) | 0.77388 (7) | 0.0430 (6) | |
H15 | 0.5193 | 0.8356 | 0.7612 | 0.052* | |
C16 | 0.5222 (4) | 1.0348 (3) | 0.76147 (8) | 0.0530 (8) | |
H16 | 0.5783 | 1.0410 | 0.7399 | 0.064* | |
N17 | 0.4835 (4) | 1.1445 (2) | 0.77724 (7) | 0.0569 (7) | |
C18 | 0.4039 (6) | 1.1327 (3) | 0.80750 (8) | 0.0648 (10) | |
H18 | 0.3732 | 1.2104 | 0.8194 | 0.078* | |
C19 | 0.3636 (4) | 1.0138 (3) | 0.82255 (7) | 0.0513 (8) | |
H19 | 0.3082 | 1.0105 | 0.8443 | 0.062* | |
C20 | 0.4705 (3) | 0.3686 (2) | 0.89534 (6) | 0.0250 (5) | |
H20 | 0.3915 | 0.3397 | 0.8768 | 0.030* | |
C21 | 0.5714 (3) | 0.2505 (2) | 0.90755 (6) | 0.0249 (5) | |
H21 | 0.6568 | 0.2756 | 0.9252 | 0.030* | |
C22 | 0.4460 (3) | 0.1521 (2) | 0.92205 (6) | 0.0260 (5) | |
H22 | 0.3760 | 0.1179 | 0.9027 | 0.031* | |
C23 | 0.3333 (3) | 0.2134 (2) | 0.94904 (6) | 0.0271 (5) | |
H23 | 0.3995 | 0.2392 | 0.9699 | 0.033* | |
C24 | 0.2474 (3) | 0.3324 (2) | 0.93358 (6) | 0.0299 (5) | |
H24 | 0.1830 | 0.3049 | 0.9126 | 0.036* | |
C30 | 0.1334 (3) | 0.4050 (2) | 0.95776 (7) | 0.0378 (6) | |
H30A | 0.0446 | 0.3461 | 0.9663 | 0.045* | |
H30B | 0.1969 | 0.4383 | 0.9779 | 0.045* | |
C31 | 0.8125 (3) | 0.1985 (3) | 0.87389 (8) | 0.0404 (6) | |
C32 | 0.4965 (3) | −0.0777 (2) | 0.92633 (6) | 0.0337 (6) | |
C33 | 0.1739 (3) | 0.1009 (3) | 0.99221 (7) | 0.0371 (6) | |
C34 | 0.1195 (3) | 0.6331 (2) | 0.94491 (7) | 0.0398 (6) | |
C35 | 0.8684 (4) | 0.1336 (3) | 0.84150 (8) | 0.0544 (8) | |
H35A | 0.9894 | 0.1427 | 0.8392 | 0.082* | |
H35B | 0.8134 | 0.1746 | 0.8216 | 0.082* | |
H35C | 0.8391 | 0.0406 | 0.8423 | 0.082* | |
C36 | 0.5863 (4) | −0.1782 (2) | 0.94682 (8) | 0.0510 (7) | |
H36A | 0.5232 | −0.1975 | 0.9679 | 0.077* | |
H36B | 0.6970 | −0.1454 | 0.9530 | 0.077* | |
H36C | 0.5978 | −0.2581 | 0.9330 | 0.077* | |
C37 | 0.0610 (4) | −0.0132 (3) | 0.99696 (8) | 0.0641 (10) | |
H37A | 0.1169 | −0.0928 | 0.9889 | 0.096* | |
H37B | −0.0413 | 0.0004 | 0.9836 | 0.096* | |
H37C | 0.0331 | −0.0224 | 1.0215 | 0.096* | |
C38 | 0.0523 (4) | 0.7278 (3) | 0.91904 (9) | 0.0583 (8) | |
H38A | 0.0242 | 0.8101 | 0.9307 | 0.088* | |
H38B | −0.0479 | 0.6913 | 0.9083 | 0.088* | |
H38C | 0.1366 | 0.7443 | 0.9012 | 0.088* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S | 0.0260 (2) | 0.0266 (3) | 0.0404 (3) | −0.0020 (3) | −0.0022 (3) | 0.0103 (3) |
O1 | 0.0273 (8) | 0.0236 (7) | 0.0324 (8) | −0.0019 (7) | 0.0022 (7) | 0.0005 (6) |
O2 | 0.0286 (8) | 0.0297 (8) | 0.0329 (8) | −0.0016 (6) | 0.0038 (7) | −0.0010 (7) |
O3 | 0.0369 (9) | 0.0236 (8) | 0.0308 (8) | 0.0009 (7) | −0.0031 (7) | 0.0037 (7) |
O4 | 0.0398 (9) | 0.0316 (9) | 0.0308 (9) | −0.0115 (8) | 0.0083 (7) | −0.0031 (7) |
O5 | 0.0338 (9) | 0.0404 (10) | 0.0500 (10) | 0.0091 (8) | −0.0030 (8) | −0.0022 (9) |
O6 | 0.0296 (11) | 0.113 (2) | 0.0930 (18) | −0.0122 (13) | −0.0010 (12) | −0.0369 (16) |
O7 | 0.0637 (12) | 0.0300 (9) | 0.0359 (10) | −0.0035 (10) | −0.0083 (10) | −0.0049 (8) |
O8 | 0.0625 (13) | 0.0567 (12) | 0.0300 (9) | −0.0102 (11) | 0.0113 (9) | −0.0045 (9) |
O9 | 0.0686 (13) | 0.0436 (11) | 0.0448 (11) | −0.0002 (11) | −0.0083 (11) | −0.0048 (9) |
N1 | 0.0357 (11) | 0.0316 (11) | 0.0487 (13) | −0.0045 (9) | −0.0093 (10) | 0.0125 (10) |
C2 | 0.0293 (11) | 0.0283 (11) | 0.0316 (12) | 0.0003 (9) | −0.0022 (10) | 0.0044 (10) |
C3 | 0.0270 (11) | 0.0251 (11) | 0.0277 (11) | 0.0000 (9) | 0.0011 (9) | 0.0006 (9) |
C4 | 0.0387 (14) | 0.0262 (12) | 0.0343 (13) | 0.0002 (10) | −0.0039 (11) | 0.0023 (10) |
C5 | 0.0462 (17) | 0.0462 (16) | 0.0661 (19) | −0.0037 (14) | −0.0157 (15) | 0.0182 (15) |
C6 | 0.068 (2) | 0.085 (3) | 0.064 (2) | 0.004 (2) | −0.0282 (19) | 0.011 (2) |
C7 | 0.0564 (19) | 0.070 (2) | 0.075 (2) | −0.0084 (19) | −0.0307 (18) | −0.0021 (19) |
C8 | 0.0603 (19) | 0.054 (2) | 0.098 (3) | −0.0101 (17) | −0.032 (2) | −0.005 (2) |
C9 | 0.0404 (14) | 0.0435 (17) | 0.073 (2) | −0.0049 (13) | −0.0074 (14) | 0.0131 (15) |
C10 | 0.0349 (13) | 0.0384 (14) | 0.0487 (16) | −0.0023 (12) | −0.0054 (12) | 0.0023 (13) |
C11 | 0.0388 (14) | 0.0371 (14) | 0.0450 (15) | −0.0023 (12) | −0.0091 (12) | 0.0076 (12) |
C12 | 0.0353 (13) | 0.0228 (11) | 0.0350 (13) | 0.0030 (10) | −0.0003 (11) | 0.0052 (10) |
N13 | 0.0376 (13) | 0.0357 (12) | 0.0630 (15) | −0.0071 (10) | −0.0111 (12) | 0.0107 (11) |
C14 | 0.0377 (13) | 0.0268 (11) | 0.0338 (13) | −0.0008 (11) | −0.0117 (11) | 0.0056 (10) |
C15 | 0.0464 (15) | 0.0326 (13) | 0.0502 (16) | 0.0014 (12) | 0.0031 (13) | 0.0073 (13) |
C16 | 0.0529 (17) | 0.0488 (18) | 0.0574 (19) | −0.0078 (14) | 0.0003 (15) | 0.0204 (15) |
N17 | 0.0739 (18) | 0.0380 (14) | 0.0587 (17) | −0.0164 (13) | −0.0271 (15) | 0.0159 (12) |
C18 | 0.117 (3) | 0.0288 (14) | 0.0487 (19) | −0.0054 (18) | −0.030 (2) | 0.0007 (13) |
C19 | 0.088 (2) | 0.0362 (14) | 0.0297 (13) | 0.0044 (16) | −0.0110 (14) | 0.0005 (12) |
C20 | 0.0259 (11) | 0.0216 (10) | 0.0275 (11) | −0.0027 (9) | 0.0004 (9) | 0.0038 (9) |
C21 | 0.0233 (11) | 0.0258 (11) | 0.0255 (11) | −0.0007 (9) | −0.0023 (9) | 0.0008 (9) |
C22 | 0.0303 (12) | 0.0216 (10) | 0.0262 (11) | −0.0015 (9) | −0.0036 (9) | 0.0031 (9) |
C23 | 0.0276 (11) | 0.0276 (11) | 0.0263 (11) | −0.0065 (9) | 0.0009 (9) | 0.0020 (9) |
C24 | 0.0263 (11) | 0.0312 (12) | 0.0322 (12) | −0.0026 (10) | 0.0012 (10) | −0.0023 (10) |
C30 | 0.0350 (14) | 0.0378 (13) | 0.0406 (14) | 0.0060 (12) | 0.0075 (12) | 0.0025 (12) |
C31 | 0.0311 (13) | 0.0344 (13) | 0.0557 (17) | 0.0005 (11) | 0.0092 (13) | 0.0029 (13) |
C32 | 0.0459 (15) | 0.0260 (12) | 0.0292 (12) | 0.0015 (11) | 0.0078 (11) | 0.0006 (10) |
C33 | 0.0426 (14) | 0.0320 (13) | 0.0366 (14) | 0.0019 (12) | 0.0139 (11) | 0.0022 (11) |
C34 | 0.0392 (14) | 0.0404 (14) | 0.0397 (14) | 0.0127 (12) | 0.0036 (13) | −0.0072 (12) |
C35 | 0.0467 (17) | 0.0448 (16) | 0.072 (2) | −0.0011 (13) | 0.0281 (16) | −0.0024 (14) |
C36 | 0.076 (2) | 0.0284 (13) | 0.0486 (16) | 0.0112 (14) | −0.0056 (16) | 0.0065 (12) |
C37 | 0.085 (2) | 0.0420 (17) | 0.066 (2) | −0.0126 (17) | 0.0454 (18) | 0.0000 (15) |
C38 | 0.068 (2) | 0.0476 (17) | 0.0599 (19) | 0.0109 (16) | −0.0065 (17) | 0.0033 (15) |
S—C2 | 1.780 (2) | C12—N13 | 1.138 (3) |
S—C20 | 1.803 (2) | C14—C19 | 1.379 (4) |
O1—C20 | 1.416 (3) | C14—C15 | 1.388 (4) |
O1—C24 | 1.441 (3) | C15—C16 | 1.380 (4) |
O2—C31 | 1.345 (3) | C15—H15 | 0.9500 |
O2—C21 | 1.440 (3) | C16—N17 | 1.315 (4) |
O3—C32 | 1.364 (3) | C16—H16 | 0.9500 |
O3—C22 | 1.442 (3) | N17—C18 | 1.338 (4) |
O4—C33 | 1.367 (3) | C18—C19 | 1.387 (4) |
O4—C23 | 1.441 (3) | C18—H18 | 0.9500 |
O5—C34 | 1.342 (3) | C19—H19 | 0.9500 |
O5—C30 | 1.447 (3) | C20—C21 | 1.529 (3) |
O6—C31 | 1.179 (3) | C20—H20 | 1.0000 |
O7—C32 | 1.192 (3) | C21—C22 | 1.529 (3) |
O8—C33 | 1.195 (3) | C21—H21 | 1.0000 |
O9—C34 | 1.198 (3) | C22—C23 | 1.516 (3) |
N1—C2 | 1.327 (3) | C22—H22 | 1.0000 |
N1—C10 | 1.346 (3) | C23—C24 | 1.521 (3) |
C2—C3 | 1.399 (3) | C23—H23 | 1.0000 |
C3—C4 | 1.390 (3) | C24—C30 | 1.504 (3) |
C3—C12 | 1.444 (3) | C24—H24 | 1.0000 |
C4—C11 | 1.404 (4) | C30—H30A | 0.9900 |
C4—C14 | 1.496 (3) | C30—H30B | 0.9900 |
C5—C6 | 1.492 (5) | C31—C35 | 1.486 (4) |
C5—C11 | 1.510 (4) | C32—C36 | 1.484 (4) |
C5—H5A | 0.9900 | C33—C37 | 1.489 (4) |
C5—H5B | 0.9900 | C34—C38 | 1.493 (4) |
C6—C7 | 1.527 (5) | C35—H35A | 0.9800 |
C6—H6A | 0.9900 | C35—H35B | 0.9800 |
C6—H6B | 0.9900 | C35—H35C | 0.9800 |
C7—C8 | 1.527 (5) | C36—H36A | 0.9800 |
C7—H7A | 0.9900 | C36—H36B | 0.9800 |
C7—H7B | 0.9900 | C36—H36C | 0.9800 |
C8—C9 | 1.490 (5) | C37—H37A | 0.9800 |
C8—H8A | 0.9900 | C37—H37B | 0.9800 |
C8—H8B | 0.9900 | C37—H37C | 0.9800 |
C9—C10 | 1.510 (4) | C38—H38A | 0.9800 |
C9—H9A | 0.9900 | C38—H38B | 0.9800 |
C9—H9B | 0.9900 | C38—H38C | 0.9800 |
C10—C11 | 1.407 (4) | ||
C2—S—C20 | 98.15 (11) | C21—C20—S | 112.40 (15) |
C20—O1—C24 | 110.72 (16) | O1—C20—H20 | 108.8 |
C31—O2—C21 | 118.2 (2) | C21—C20—H20 | 108.8 |
C32—O3—C22 | 116.89 (18) | S—C20—H20 | 108.8 |
C33—O4—C23 | 117.14 (19) | O2—C21—C20 | 108.50 (17) |
C34—O5—C30 | 117.8 (2) | O2—C21—C22 | 106.38 (17) |
C2—N1—C10 | 119.1 (2) | C20—C21—C22 | 106.52 (17) |
N1—C2—C3 | 121.7 (2) | O2—C21—H21 | 111.7 |
N1—C2—S | 118.82 (17) | C20—C21—H21 | 111.7 |
C3—C2—S | 119.42 (17) | C22—C21—H21 | 111.7 |
C4—C3—C2 | 119.5 (2) | O3—C22—C23 | 108.80 (18) |
C4—C3—C12 | 120.8 (2) | O3—C22—C21 | 109.10 (17) |
C2—C3—C12 | 119.7 (2) | C23—C22—C21 | 111.88 (18) |
C3—C4—C11 | 119.1 (2) | O3—C22—H22 | 109.0 |
C3—C4—C14 | 119.4 (2) | C23—C22—H22 | 109.0 |
C11—C4—C14 | 121.5 (2) | C21—C22—H22 | 109.0 |
C6—C5—C11 | 115.2 (3) | O4—C23—C22 | 105.63 (17) |
C6—C5—H5A | 108.5 | O4—C23—C24 | 110.98 (18) |
C11—C5—H5A | 108.5 | C22—C23—C24 | 109.32 (18) |
C6—C5—H5B | 108.5 | O4—C23—H23 | 110.3 |
C11—C5—H5B | 108.5 | C22—C23—H23 | 110.3 |
H5A—C5—H5B | 107.5 | C24—C23—H23 | 110.3 |
C5—C6—C7 | 114.9 (3) | O1—C24—C30 | 107.60 (19) |
C5—C6—H6A | 108.5 | O1—C24—C23 | 106.49 (17) |
C7—C6—H6A | 108.5 | C30—C24—C23 | 115.3 (2) |
C5—C6—H6B | 108.5 | O1—C24—H24 | 109.1 |
C7—C6—H6B | 108.5 | C30—C24—H24 | 109.1 |
H6A—C6—H6B | 107.5 | C23—C24—H24 | 109.1 |
C8—C7—C6 | 114.9 (3) | O5—C30—C24 | 107.6 (2) |
C8—C7—H7A | 108.5 | O5—C30—H30A | 110.2 |
C6—C7—H7A | 108.5 | C24—C30—H30A | 110.2 |
C8—C7—H7B | 108.5 | O5—C30—H30B | 110.2 |
C6—C7—H7B | 108.5 | C24—C30—H30B | 110.2 |
H7A—C7—H7B | 107.5 | H30A—C30—H30B | 108.5 |
C9—C8—C7 | 115.2 (3) | O6—C31—O2 | 123.4 (3) |
C9—C8—H8A | 108.5 | O6—C31—C35 | 125.4 (3) |
C7—C8—H8A | 108.5 | O2—C31—C35 | 111.2 (3) |
C9—C8—H8B | 108.5 | O7—C32—O3 | 123.3 (2) |
C7—C8—H8B | 108.5 | O7—C32—C36 | 125.9 (2) |
H8A—C8—H8B | 107.5 | O3—C32—C36 | 110.8 (2) |
C8—C9—C10 | 114.8 (3) | O8—C33—O4 | 122.5 (2) |
C8—C9—H9A | 108.6 | O8—C33—C37 | 127.8 (3) |
C10—C9—H9A | 108.6 | O4—C33—C37 | 109.7 (2) |
C8—C9—H9B | 108.6 | O9—C34—O5 | 124.4 (2) |
C10—C9—H9B | 108.6 | O9—C34—C38 | 125.1 (3) |
H9A—C9—H9B | 107.5 | O5—C34—C38 | 110.5 (2) |
N1—C10—C11 | 123.2 (2) | C31—C35—H35A | 109.5 |
N1—C10—C9 | 114.7 (2) | C31—C35—H35B | 109.5 |
C11—C10—C9 | 122.1 (2) | H35A—C35—H35B | 109.5 |
C4—C11—C10 | 117.0 (2) | C31—C35—H35C | 109.5 |
C4—C11—C5 | 122.8 (2) | H35A—C35—H35C | 109.5 |
C10—C11—C5 | 120.3 (2) | H35B—C35—H35C | 109.5 |
N13—C12—C3 | 178.8 (3) | C32—C36—H36A | 109.5 |
C19—C14—C15 | 118.0 (2) | C32—C36—H36B | 109.5 |
C19—C14—C4 | 121.3 (2) | H36A—C36—H36B | 109.5 |
C15—C14—C4 | 120.7 (2) | C32—C36—H36C | 109.5 |
C16—C15—C14 | 118.3 (3) | H36A—C36—H36C | 109.5 |
C16—C15—H15 | 120.9 | H36B—C36—H36C | 109.5 |
C14—C15—H15 | 120.9 | C33—C37—H37A | 109.5 |
N17—C16—C15 | 125.0 (3) | C33—C37—H37B | 109.5 |
N17—C16—H16 | 117.5 | H37A—C37—H37B | 109.5 |
C15—C16—H16 | 117.5 | C33—C37—H37C | 109.5 |
C16—N17—C18 | 116.1 (3) | H37A—C37—H37C | 109.5 |
N17—C18—C19 | 123.8 (3) | H37B—C37—H37C | 109.5 |
N17—C18—H18 | 118.1 | C34—C38—H38A | 109.5 |
C19—C18—H18 | 118.1 | C34—C38—H38B | 109.5 |
C14—C19—C18 | 118.7 (3) | H38A—C38—H38B | 109.5 |
C14—C19—H19 | 120.7 | C34—C38—H38C | 109.5 |
C18—C19—H19 | 120.7 | H38A—C38—H38C | 109.5 |
O1—C20—C21 | 110.08 (17) | H38B—C38—H38C | 109.5 |
O1—C20—S | 107.84 (14) | ||
C10—N1—C2—C3 | 0.1 (4) | C4—C14—C19—C18 | −179.9 (3) |
C10—N1—C2—S | 178.7 (2) | N17—C18—C19—C14 | −0.8 (5) |
C20—S—C2—N1 | −10.7 (2) | C24—O1—C20—C21 | −68.6 (2) |
C20—S—C2—C3 | 167.95 (19) | C24—O1—C20—S | 168.46 (14) |
N1—C2—C3—C4 | −5.6 (4) | C2—S—C20—O1 | −78.05 (16) |
S—C2—C3—C4 | 175.83 (18) | C2—S—C20—C21 | 160.43 (17) |
N1—C2—C3—C12 | 173.3 (2) | C31—O2—C21—C20 | 110.0 (2) |
S—C2—C3—C12 | −5.3 (3) | C31—O2—C21—C22 | −135.8 (2) |
C2—C3—C4—C11 | 5.1 (4) | O1—C20—C21—O2 | 172.45 (16) |
C12—C3—C4—C11 | −173.7 (2) | S—C20—C21—O2 | −67.3 (2) |
C2—C3—C4—C14 | −178.2 (2) | O1—C20—C21—C22 | 58.3 (2) |
C12—C3—C4—C14 | 2.9 (3) | S—C20—C21—C22 | 178.51 (15) |
C11—C5—C6—C7 | 80.5 (4) | C32—O3—C22—C23 | 112.3 (2) |
C5—C6—C7—C8 | −63.8 (4) | C32—O3—C22—C21 | −125.4 (2) |
C6—C7—C8—C9 | 61.4 (5) | O2—C21—C22—O3 | 71.0 (2) |
C7—C8—C9—C10 | −77.5 (4) | C20—C21—C22—O3 | −173.38 (17) |
C2—N1—C10—C11 | 5.8 (4) | O2—C21—C22—C23 | −168.55 (17) |
C2—N1—C10—C9 | −174.0 (3) | C20—C21—C22—C23 | −52.9 (2) |
C8—C9—C10—N1 | −114.2 (3) | C33—O4—C23—C22 | 138.5 (2) |
C8—C9—C10—C11 | 66.0 (4) | C33—O4—C23—C24 | −103.1 (2) |
C3—C4—C11—C10 | 0.4 (4) | O3—C22—C23—O4 | −64.3 (2) |
C14—C4—C11—C10 | −176.2 (2) | C21—C22—C23—O4 | 175.06 (17) |
C3—C4—C11—C5 | 179.4 (3) | O3—C22—C23—C24 | 176.19 (17) |
C14—C4—C11—C5 | 2.8 (4) | C21—C22—C23—C24 | 55.6 (2) |
N1—C10—C11—C4 | −6.0 (4) | C20—O1—C24—C30 | −168.38 (18) |
C9—C10—C11—C4 | 173.8 (3) | C20—O1—C24—C23 | 67.5 (2) |
N1—C10—C11—C5 | 175.0 (3) | O4—C23—C24—O1 | −175.80 (17) |
C9—C10—C11—C5 | −5.2 (4) | C22—C23—C24—O1 | −59.7 (2) |
C6—C5—C11—C4 | 121.1 (3) | O4—C23—C24—C30 | 65.0 (3) |
C6—C5—C11—C10 | −59.9 (4) | C22—C23—C24—C30 | −178.9 (2) |
C4—C3—C12—N13 | 126 (12) | C34—O5—C30—C24 | −104.6 (2) |
C2—C3—C12—N13 | −53 (12) | O1—C24—C30—O5 | 62.4 (2) |
C3—C4—C14—C19 | −91.6 (3) | C23—C24—C30—O5 | −178.97 (19) |
C11—C4—C14—C19 | 85.0 (3) | C21—O2—C31—O6 | −0.3 (4) |
C3—C4—C14—C15 | 88.0 (3) | C21—O2—C31—C35 | −178.5 (2) |
C11—C4—C14—C15 | −95.4 (3) | C22—O3—C32—O7 | 4.8 (3) |
C19—C14—C15—C16 | −0.2 (4) | C22—O3—C32—C36 | −174.9 (2) |
C4—C14—C15—C16 | −179.8 (3) | C23—O4—C33—O8 | 5.7 (4) |
C14—C15—C16—N17 | 0.1 (5) | C23—O4—C33—C37 | −175.1 (2) |
C15—C16—N17—C18 | −0.3 (5) | C30—O5—C34—O9 | −9.4 (4) |
C16—N17—C18—C19 | 0.7 (5) | C30—O5—C34—C38 | 170.5 (2) |
C15—C14—C19—C18 | 0.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C37—H37C···O1i | 0.98 | 2.68 | 3.544 (3) | 147 |
C24—H24···O6ii | 1.00 | 2.45 | 3.288 (3) | 142 |
C19—H19···O7iii | 0.95 | 2.64 | 3.332 (3) | 130 |
C38—H38C···O7iii | 0.98 | 2.67 | 3.379 (4) | 129 |
C21—H21···O8iv | 1.00 | 2.47 | 3.364 (3) | 149 |
C5—H5A···N13ii | 0.99 | 2.59 | 3.561 (4) | 168 |
C35—H35C···N13v | 0.98 | 2.44 | 3.401 (4) | 168 |
C15—H15···N17vi | 0.95 | 2.45 | 3.375 (4) | 163 |
Symmetry codes: (i) x−1/2, −y+1/2, −z+2; (ii) x−1, y, z; (iii) x, y+1, z; (iv) x+1/2, −y+1/2, −z+2; (v) x, y−1, z; (vi) −x+1, y−1/2, −z+3/2. |