organic compounds
The title compound, C18H17NO3S, is the product of an epoxidation reaction, followed by cyclization and hydrolysis of the resulting epoxide. There are two independent molecules in the asymmetric unit; one has a slightly twisted heterocyclic ring, and the ring in the other is almost planar. Molecules form centrosymmetric pairs through N—HO=C hydrogen bonds, involving the carbonyl group in the ring.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802010735/bt6153sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802010735/bt6153Isup2.hkl |
CCDC reference: 189904
Key indicators
- Single-crystal X-ray study
- T = 160 K
- Mean (C-C) = 0.005 Å
- R factor = 0.073
- wR factor = 0.145
- Data-to-parameter ratio = 15.5
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 1.053 Tmax scaled 0.985 Tmin scaled 0.889
Computing details top
Data collection: SMART (Siemens, 1995); cell refinement: local programs; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 1994); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.
(4RS,5RS)-4-Benzyl-5-(4-tolylthiocarbonyl)oxazolidin-2-one top
Crystal data top
C18H17NO3S | F(000) = 1376 |
Mr = 327.39 | Dx = 1.309 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 22.696 (3) Å | Cell parameters from 4377 reflections |
b = 6.2094 (8) Å | θ = 1.7–24.6° |
c = 24.555 (3) Å | µ = 0.21 mm−1 |
β = 106.205 (3)° | T = 160 K |
V = 3323.0 (7) Å3 | Plate, colourless |
Z = 8 | 0.56 × 0.14 × 0.07 mm |
Data collection top
Siemens SMART 1K CCD diffractometer | 6588 independent reflections |
Radiation source: sealed tube | 3940 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.070 |
Detector resolution: 8.192 pixels mm-1 | θmax = 26.3°, θmin = 1.7° |
ω rotation with narrow frames scans | h = −27→21 |
Absorption correction: multi-scan (XPREP in SHELXTL; Sheldrick, 1994) | k = −7→7 |
Tmin = 0.844, Tmax = 0.936 | l = −29→30 |
16452 measured reflections |
Refinement top
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)] = 0.073 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.145 | w = 1/[σ2(Fo2) + (0.0292P)2 + 4.1967P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max = 0.006 |
6588 reflections | Δρmax = 0.32 e Å−3 |
424 parameters | Δρmin = −0.26 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0014 (2) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.06024 (12) | 1.1506 (4) | 0.04677 (10) | 0.0480 (7) | |
C1 | 0.03424 (18) | 1.0806 (6) | 0.08004 (15) | 0.0383 (9) | |
O2 | 0.04911 (12) | 1.1574 (4) | 0.13487 (10) | 0.0423 (7) | |
C2 | 0.01549 (18) | 1.0380 (6) | 0.16668 (15) | 0.0417 (10) | |
H2A | −0.0049 | 1.1409 | 0.1870 | 0.050* | |
C3 | −0.03426 (19) | 0.9134 (7) | 0.12144 (15) | 0.0437 (10) | |
H3 | −0.0740 | 0.9937 | 0.1130 | 0.052* | |
N1 | −0.00896 (15) | 0.9309 (5) | 0.07346 (13) | 0.0382 (8) | |
H1 | −0.0258 (18) | 0.893 (7) | 0.0420 (15) | 0.046* | |
C4 | −0.0443 (2) | 0.6825 (7) | 0.13687 (17) | 0.0571 (12) | |
H4A | −0.0580 | 0.6817 | 0.1717 | 0.069* | |
H4B | −0.0048 | 0.6040 | 0.1451 | 0.069* | |
C5 | −0.0914 (2) | 0.5657 (7) | 0.09007 (17) | 0.0509 (12) | |
C6 | −0.1529 (2) | 0.5690 (9) | 0.08728 (18) | 0.0661 (14) | |
H6 | −0.1663 | 0.6486 | 0.1146 | 0.079* | |
C7 | −0.1952 (2) | 0.4583 (9) | 0.0453 (2) | 0.0732 (15) | |
H7 | −0.2375 | 0.4617 | 0.0440 | 0.088* | |
C8 | −0.1761 (2) | 0.3433 (8) | 0.0057 (2) | 0.0637 (14) | |
H8 | −0.2051 | 0.2636 | −0.0225 | 0.076* | |
C9 | −0.1156 (2) | 0.3428 (7) | 0.00648 (19) | 0.0613 (13) | |
H9 | −0.1027 | 0.2668 | −0.0218 | 0.074* | |
C10 | −0.0732 (2) | 0.4537 (7) | 0.04873 (19) | 0.0570 (12) | |
H10 | −0.0311 | 0.4530 | 0.0494 | 0.068* | |
C11 | 0.05887 (18) | 0.8926 (6) | 0.20995 (16) | 0.0436 (10) | |
O3 | 0.04889 (14) | 0.8368 (5) | 0.25343 (11) | 0.0571 (8) | |
S1 | 0.12376 (5) | 0.81572 (19) | 0.18834 (4) | 0.0475 (3) | |
C12 | 0.16347 (18) | 0.6361 (7) | 0.24307 (16) | 0.0426 (10) | |
C13 | 0.17624 (18) | 0.4320 (7) | 0.22782 (17) | 0.0466 (11) | |
H13 | 0.1574 | 0.3804 | 0.1906 | 0.056* | |
C14 | 0.21643 (18) | 0.3021 (7) | 0.26665 (16) | 0.0459 (10) | |
H14 | 0.2251 | 0.1617 | 0.2555 | 0.055* | |
C15 | 0.24450 (18) | 0.3712 (7) | 0.32146 (16) | 0.0433 (10) | |
C16 | 0.2285 (2) | 0.5747 (7) | 0.33639 (17) | 0.0576 (13) | |
H16 | 0.2454 | 0.6236 | 0.3742 | 0.069* | |
C17 | 0.1888 (2) | 0.7083 (7) | 0.29780 (17) | 0.0588 (13) | |
H17 | 0.1792 | 0.8476 | 0.3088 | 0.071* | |
C18 | 0.2917 (2) | 0.2348 (7) | 0.36194 (19) | 0.0618 (13) | |
H18A | 0.2851 | 0.2411 | 0.3997 | 0.093* | |
H18B | 0.3328 | 0.2889 | 0.3640 | 0.093* | |
H18C | 0.2880 | 0.0854 | 0.3486 | 0.093* | |
O4 | 0.44831 (11) | 0.3418 (4) | 0.44597 (9) | 0.0318 (6) | |
C19 | 0.47389 (16) | 0.4528 (5) | 0.41827 (13) | 0.0275 (8) | |
O5 | 0.46145 (11) | 0.4188 (4) | 0.36105 (9) | 0.0341 (6) | |
C20 | 0.49661 (17) | 0.5672 (5) | 0.33757 (13) | 0.0303 (8) | |
H20 | 0.5252 | 0.4836 | 0.3211 | 0.036* | |
C21 | 0.53527 (17) | 0.7036 (5) | 0.38864 (13) | 0.0293 (8) | |
H21 | 0.5796 | 0.6657 | 0.3958 | 0.035* | |
N2 | 0.51271 (14) | 0.6140 (5) | 0.43364 (11) | 0.0303 (7) | |
H2 | 0.5279 (16) | 0.638 (6) | 0.4656 (14) | 0.036* | |
C22 | 0.52799 (17) | 0.9464 (5) | 0.38215 (14) | 0.0346 (9) | |
H22A | 0.5293 | 0.9865 | 0.3435 | 0.042* | |
H22B | 0.4870 | 0.9867 | 0.3857 | 0.042* | |
C23 | 0.57609 (16) | 1.0762 (5) | 0.42464 (14) | 0.0301 (8) | |
C24 | 0.57951 (17) | 1.0749 (6) | 0.48245 (14) | 0.0347 (9) | |
H24 | 0.5523 | 0.9858 | 0.4956 | 0.042* | |
C25 | 0.62166 (17) | 1.2007 (6) | 0.52060 (15) | 0.0374 (9) | |
H25 | 0.6237 | 1.1957 | 0.5598 | 0.045* | |
C26 | 0.66077 (17) | 1.3337 (6) | 0.50213 (15) | 0.0384 (9) | |
H26 | 0.6890 | 1.4236 | 0.5282 | 0.046* | |
C27 | 0.65852 (17) | 1.3347 (6) | 0.44532 (16) | 0.0381 (9) | |
H27 | 0.6858 | 1.4245 | 0.4324 | 0.046* | |
C28 | 0.61700 (16) | 1.2066 (6) | 0.40701 (14) | 0.0328 (9) | |
H28 | 0.6164 | 1.2077 | 0.3682 | 0.039* | |
C29 | 0.45279 (16) | 0.6945 (5) | 0.29055 (13) | 0.0304 (8) | |
O6 | 0.46932 (12) | 0.7674 (4) | 0.25180 (10) | 0.0397 (7) | |
S2 | 0.37844 (5) | 0.72526 (15) | 0.29963 (4) | 0.0367 (3) | |
C30 | 0.34413 (16) | 0.8991 (6) | 0.24202 (14) | 0.0311 (8) | |
C31 | 0.36731 (18) | 1.1034 (6) | 0.23738 (15) | 0.0374 (9) | |
H31 | 0.4032 | 1.1530 | 0.2646 | 0.045* | |
C32 | 0.33720 (18) | 1.2334 (6) | 0.19249 (15) | 0.0399 (9) | |
H32 | 0.3536 | 1.3717 | 0.1889 | 0.048* | |
C33 | 0.28404 (18) | 1.1689 (6) | 0.15260 (15) | 0.0376 (9) | |
C34 | 0.26172 (17) | 0.9643 (6) | 0.15820 (15) | 0.0383 (9) | |
H34 | 0.2255 | 0.9156 | 0.1312 | 0.046* | |
C35 | 0.29145 (17) | 0.8297 (6) | 0.20251 (14) | 0.0349 (9) | |
H35 | 0.2756 | 0.6901 | 0.2057 | 0.042* | |
C36 | 0.2514 (2) | 1.3130 (7) | 0.10403 (16) | 0.0533 (12) | |
H36A | 0.2163 | 1.2358 | 0.0794 | 0.080* | |
H36B | 0.2798 | 1.3539 | 0.0822 | 0.080* | |
H36C | 0.2369 | 1.4427 | 0.1190 | 0.080* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0569 (18) | 0.0559 (18) | 0.0332 (15) | −0.0149 (15) | 0.0160 (13) | 0.0004 (14) |
C1 | 0.041 (2) | 0.043 (2) | 0.029 (2) | 0.000 (2) | 0.0054 (18) | 0.0016 (18) |
O2 | 0.0541 (17) | 0.0428 (16) | 0.0292 (14) | −0.0077 (14) | 0.0105 (12) | −0.0022 (12) |
C2 | 0.048 (2) | 0.049 (2) | 0.031 (2) | 0.000 (2) | 0.0143 (18) | −0.0030 (19) |
C3 | 0.047 (2) | 0.052 (3) | 0.032 (2) | −0.004 (2) | 0.0102 (18) | 0.0029 (19) |
N1 | 0.041 (2) | 0.045 (2) | 0.0284 (17) | −0.0081 (17) | 0.0092 (15) | 0.0019 (16) |
C4 | 0.063 (3) | 0.064 (3) | 0.037 (2) | −0.015 (3) | 0.003 (2) | 0.015 (2) |
C5 | 0.054 (3) | 0.055 (3) | 0.036 (2) | −0.017 (2) | −0.001 (2) | 0.016 (2) |
C6 | 0.053 (3) | 0.101 (4) | 0.044 (3) | −0.032 (3) | 0.014 (2) | −0.010 (3) |
C7 | 0.055 (3) | 0.104 (4) | 0.062 (3) | −0.027 (3) | 0.018 (3) | −0.010 (3) |
C8 | 0.064 (3) | 0.061 (3) | 0.053 (3) | −0.016 (3) | −0.005 (3) | 0.005 (3) |
C9 | 0.070 (3) | 0.049 (3) | 0.058 (3) | 0.005 (3) | 0.005 (3) | −0.002 (2) |
C10 | 0.053 (3) | 0.045 (3) | 0.064 (3) | 0.001 (2) | 0.003 (2) | 0.006 (2) |
C11 | 0.051 (3) | 0.042 (2) | 0.034 (2) | −0.009 (2) | 0.0060 (19) | −0.0058 (19) |
O3 | 0.073 (2) | 0.075 (2) | 0.0274 (14) | −0.0062 (18) | 0.0204 (14) | 0.0069 (15) |
S1 | 0.0451 (6) | 0.0609 (7) | 0.0373 (6) | 0.0007 (6) | 0.0128 (5) | 0.0044 (5) |
C12 | 0.041 (2) | 0.050 (3) | 0.036 (2) | −0.002 (2) | 0.0093 (18) | −0.006 (2) |
C13 | 0.047 (3) | 0.050 (3) | 0.039 (2) | −0.012 (2) | 0.006 (2) | −0.010 (2) |
C14 | 0.050 (3) | 0.042 (2) | 0.046 (2) | −0.006 (2) | 0.013 (2) | −0.008 (2) |
C15 | 0.040 (2) | 0.044 (2) | 0.043 (2) | −0.002 (2) | 0.0068 (19) | −0.001 (2) |
C16 | 0.075 (3) | 0.051 (3) | 0.036 (2) | 0.003 (3) | −0.003 (2) | −0.011 (2) |
C17 | 0.075 (3) | 0.045 (3) | 0.048 (3) | 0.009 (2) | 0.003 (2) | −0.010 (2) |
C18 | 0.058 (3) | 0.056 (3) | 0.062 (3) | 0.005 (2) | 0.002 (2) | −0.005 (2) |
O4 | 0.0442 (15) | 0.0293 (13) | 0.0219 (12) | −0.0042 (12) | 0.0091 (11) | 0.0034 (11) |
C19 | 0.038 (2) | 0.0223 (19) | 0.0203 (18) | 0.0092 (17) | 0.0041 (16) | 0.0029 (15) |
O5 | 0.0603 (17) | 0.0225 (13) | 0.0189 (12) | −0.0065 (12) | 0.0098 (11) | 0.0026 (10) |
C20 | 0.047 (2) | 0.0254 (19) | 0.0206 (17) | 0.0051 (17) | 0.0130 (16) | 0.0011 (15) |
C21 | 0.040 (2) | 0.0280 (19) | 0.0224 (17) | 0.0040 (17) | 0.0120 (16) | 0.0054 (15) |
N2 | 0.047 (2) | 0.0264 (17) | 0.0174 (14) | −0.0051 (15) | 0.0095 (14) | −0.0030 (13) |
C22 | 0.048 (2) | 0.028 (2) | 0.0280 (19) | 0.0018 (18) | 0.0102 (17) | 0.0011 (16) |
C23 | 0.038 (2) | 0.0228 (19) | 0.0298 (19) | 0.0044 (17) | 0.0091 (16) | 0.0024 (16) |
C24 | 0.047 (2) | 0.029 (2) | 0.032 (2) | 0.0013 (19) | 0.0157 (17) | 0.0034 (17) |
C25 | 0.046 (2) | 0.037 (2) | 0.0262 (19) | 0.009 (2) | 0.0063 (17) | 0.0004 (18) |
C26 | 0.038 (2) | 0.038 (2) | 0.033 (2) | 0.0019 (19) | −0.0003 (17) | −0.0016 (18) |
C27 | 0.036 (2) | 0.033 (2) | 0.048 (2) | −0.0006 (19) | 0.0162 (18) | 0.0072 (19) |
C28 | 0.043 (2) | 0.032 (2) | 0.0265 (18) | 0.0060 (18) | 0.0151 (17) | 0.0035 (17) |
C29 | 0.047 (2) | 0.0244 (19) | 0.0220 (18) | 0.0019 (17) | 0.0132 (16) | −0.0036 (15) |
O6 | 0.0560 (17) | 0.0410 (16) | 0.0271 (13) | 0.0073 (13) | 0.0201 (12) | 0.0094 (12) |
S2 | 0.0457 (6) | 0.0365 (6) | 0.0295 (5) | −0.0011 (5) | 0.0131 (4) | 0.0070 (4) |
C30 | 0.039 (2) | 0.031 (2) | 0.0256 (18) | 0.0000 (17) | 0.0119 (16) | −0.0006 (16) |
C31 | 0.044 (2) | 0.031 (2) | 0.033 (2) | −0.0030 (19) | 0.0049 (18) | −0.0032 (17) |
C32 | 0.050 (2) | 0.031 (2) | 0.042 (2) | 0.0005 (19) | 0.0176 (19) | 0.0034 (18) |
C33 | 0.046 (2) | 0.035 (2) | 0.032 (2) | 0.0079 (19) | 0.0124 (18) | 0.0013 (18) |
C34 | 0.037 (2) | 0.046 (2) | 0.032 (2) | −0.001 (2) | 0.0100 (17) | −0.0066 (19) |
C35 | 0.044 (2) | 0.030 (2) | 0.034 (2) | −0.0041 (19) | 0.0168 (18) | −0.0020 (17) |
C36 | 0.072 (3) | 0.048 (3) | 0.036 (2) | 0.014 (2) | 0.009 (2) | 0.007 (2) |
Geometric parameters (Å, º) top
O1—C1 | 1.214 (4) | O4—C19 | 1.223 (4) |
C1—O2 | 1.379 (4) | C19—O5 | 1.370 (4) |
C1—N1 | 1.327 (5) | C19—N2 | 1.317 (4) |
O2—C2 | 1.441 (4) | O5—C20 | 1.441 (4) |
C2—H2A | 1.000 | C20—H20 | 1.000 |
C2—C3 | 1.551 (5) | C20—C21 | 1.564 (4) |
C2—C11 | 1.526 (5) | C20—C29 | 1.519 (4) |
C3—H3 | 1.000 | C21—H21 | 1.000 |
C3—N1 | 1.452 (5) | C21—N2 | 1.452 (4) |
C3—C4 | 1.516 (6) | C21—C22 | 1.520 (5) |
N1—H1 | 0.79 (4) | N2—H2 | 0.78 (3) |
C4—H4A | 0.990 | C22—H22A | 0.990 |
C4—H4B | 0.990 | C22—H22B | 0.990 |
C4—C5 | 1.518 (5) | C22—C23 | 1.515 (5) |
C5—C6 | 1.378 (6) | C23—C24 | 1.400 (5) |
C5—C10 | 1.386 (6) | C23—C28 | 1.389 (5) |
C6—H6 | 0.950 | C24—H24 | 0.950 |
C6—C7 | 1.380 (6) | C24—C25 | 1.379 (5) |
C7—H7 | 0.950 | C25—H25 | 0.950 |
C7—C8 | 1.372 (7) | C25—C26 | 1.378 (5) |
C8—H8 | 0.950 | C26—H26 | 0.950 |
C8—C9 | 1.368 (6) | C26—C27 | 1.382 (5) |
C9—H9 | 0.950 | C27—H27 | 0.950 |
C9—C10 | 1.386 (6) | C27—C28 | 1.383 (5) |
C10—H10 | 0.950 | C28—H28 | 0.950 |
C11—O3 | 1.203 (4) | C29—O6 | 1.204 (4) |
C11—S1 | 1.765 (4) | C29—S2 | 1.773 (4) |
S1—C12 | 1.785 (4) | S2—C30 | 1.777 (3) |
C12—C13 | 1.375 (5) | C30—C31 | 1.390 (5) |
C12—C17 | 1.381 (5) | C30—C35 | 1.382 (5) |
C13—H13 | 0.950 | C31—H31 | 0.950 |
C13—C14 | 1.381 (5) | C31—C32 | 1.383 (5) |
C14—H14 | 0.950 | C32—H32 | 0.950 |
C14—C15 | 1.387 (5) | C32—C33 | 1.384 (5) |
C15—C16 | 1.391 (6) | C33—C34 | 1.388 (5) |
C15—C18 | 1.503 (5) | C33—C36 | 1.510 (5) |
C16—H16 | 0.950 | C34—H34 | 0.950 |
C16—C17 | 1.386 (6) | C34—C35 | 1.388 (5) |
C17—H17 | 0.950 | C35—H35 | 0.950 |
C18—H18A | 0.980 | C36—H36A | 0.980 |
C18—H18B | 0.980 | C36—H36B | 0.980 |
C18—H18C | 0.980 | C36—H36C | 0.980 |
O1—C1—O2 | 120.0 (4) | O4—C19—O5 | 119.3 (3) |
O1—C1—N1 | 130.5 (4) | O4—C19—N2 | 130.7 (3) |
O2—C1—N1 | 109.4 (3) | O5—C19—N2 | 109.9 (3) |
C1—O2—C2 | 109.2 (3) | C19—O5—C20 | 109.5 (3) |
O2—C2—H2A | 109.3 | O5—C20—H20 | 108.9 |
O2—C2—C3 | 105.0 (3) | O5—C20—C21 | 106.0 (2) |
O2—C2—C11 | 110.2 (3) | O5—C20—C29 | 108.6 (3) |
H2A—C2—C3 | 109.3 | H20—C20—C21 | 108.9 |
H2A—C2—C11 | 109.3 | H20—C20—C29 | 108.9 |
C3—C2—C11 | 113.8 (3) | C21—C20—C29 | 115.4 (3) |
C2—C3—H3 | 109.5 | C20—C21—H21 | 109.1 |
C2—C3—N1 | 99.8 (3) | C20—C21—N2 | 99.5 (3) |
C2—C3—C4 | 115.0 (3) | C20—C21—C22 | 115.6 (3) |
H3—C3—N1 | 109.5 | H21—C21—N2 | 109.1 |
H3—C3—C4 | 109.5 | H21—C21—C22 | 109.1 |
N1—C3—C4 | 113.2 (3) | N2—C21—C22 | 114.1 (3) |
C1—N1—C3 | 113.6 (3) | C19—N2—C21 | 115.0 (3) |
C1—N1—H1 | 118 (3) | C19—N2—H2 | 120 (3) |
C3—N1—H1 | 125 (3) | C21—N2—H2 | 123 (3) |
C3—C4—H4A | 109.1 | C21—C22—H22A | 108.6 |
C3—C4—H4B | 109.1 | C21—C22—H22B | 108.6 |
C3—C4—C5 | 112.7 (3) | C21—C22—C23 | 114.8 (3) |
H4A—C4—H4B | 107.8 | H22A—C22—H22B | 107.6 |
H4A—C4—C5 | 109.1 | H22A—C22—C23 | 108.6 |
H4B—C4—C5 | 109.1 | H22B—C22—C23 | 108.6 |
C4—C5—C6 | 121.4 (4) | C22—C23—C24 | 121.4 (3) |
C4—C5—C10 | 120.2 (4) | C22—C23—C28 | 120.8 (3) |
C6—C5—C10 | 118.4 (4) | C24—C23—C28 | 117.8 (3) |
C5—C6—H6 | 119.5 | C23—C24—H24 | 119.4 |
C5—C6—C7 | 121.0 (5) | C23—C24—C25 | 121.1 (4) |
H6—C6—C7 | 119.5 | H24—C24—C25 | 119.4 |
C6—C7—H7 | 120.1 | C24—C25—H25 | 119.9 |
C6—C7—C8 | 119.8 (5) | C24—C25—C26 | 120.3 (3) |
H7—C7—C8 | 120.1 | H25—C25—C26 | 119.9 |
C7—C8—H8 | 119.8 | C25—C26—H26 | 120.3 |
C7—C8—C9 | 120.4 (5) | C25—C26—C27 | 119.3 (3) |
H8—C8—C9 | 119.8 | H26—C26—C27 | 120.3 |
C8—C9—H9 | 120.2 | C26—C27—H27 | 119.7 |
C8—C9—C10 | 119.7 (5) | C26—C27—C28 | 120.7 (3) |
H9—C9—C10 | 120.2 | H27—C27—C28 | 119.7 |
C5—C10—C9 | 120.7 (4) | C23—C28—C27 | 120.8 (3) |
C5—C10—H10 | 119.7 | C23—C28—H28 | 119.6 |
C9—C10—H10 | 119.7 | C27—C28—H28 | 119.6 |
C2—C11—O3 | 122.9 (4) | C20—C29—O6 | 120.9 (3) |
C2—C11—S1 | 112.4 (3) | C20—C29—S2 | 113.9 (2) |
O3—C11—S1 | 124.7 (3) | O6—C29—S2 | 125.2 (3) |
C11—S1—C12 | 103.35 (19) | C29—S2—C30 | 100.73 (16) |
S1—C12—C13 | 118.1 (3) | S2—C30—C31 | 121.9 (3) |
S1—C12—C17 | 121.0 (3) | S2—C30—C35 | 118.1 (3) |
C13—C12—C17 | 120.1 (4) | C31—C30—C35 | 120.0 (3) |
C12—C13—H13 | 120.0 | C30—C31—H31 | 120.5 |
C12—C13—C14 | 120.0 (4) | C30—C31—C32 | 118.9 (3) |
H13—C13—C14 | 120.0 | H31—C31—C32 | 120.5 |
C13—C14—H14 | 119.2 | C31—C32—H32 | 118.8 |
C13—C14—C15 | 121.7 (4) | C31—C32—C33 | 122.3 (4) |
H14—C14—C15 | 119.2 | H32—C32—C33 | 118.8 |
C14—C15—C16 | 117.0 (4) | C32—C33—C34 | 117.7 (3) |
C14—C15—C18 | 121.1 (4) | C32—C33—C36 | 121.8 (4) |
C16—C15—C18 | 121.8 (4) | C34—C33—C36 | 120.5 (4) |
C15—C16—H16 | 119.0 | C33—C34—H34 | 119.4 |
C15—C16—C17 | 122.1 (4) | C33—C34—C35 | 121.2 (4) |
H16—C16—C17 | 119.0 | H34—C34—C35 | 119.4 |
C12—C17—C16 | 119.1 (4) | C30—C35—C34 | 119.9 (3) |
C12—C17—H17 | 120.5 | C30—C35—H35 | 120.1 |
C16—C17—H17 | 120.5 | C34—C35—H35 | 120.1 |
C15—C18—H18A | 109.5 | C33—C36—H36A | 109.5 |
C15—C18—H18B | 109.5 | C33—C36—H36B | 109.5 |
C15—C18—H18C | 109.5 | C33—C36—H36C | 109.5 |
H18A—C18—H18B | 109.5 | H36A—C36—H36B | 109.5 |
H18A—C18—H18C | 109.5 | H36A—C36—H36C | 109.5 |
H18B—C18—H18C | 109.5 | H36B—C36—H36C | 109.5 |
O1—C1—O2—C2 | −175.7 (3) | O4—C19—O5—C20 | −180.0 (3) |
N1—C1—O2—C2 | 3.8 (4) | N2—C19—O5—C20 | 1.7 (4) |
C1—O2—C2—C11 | 109.5 (3) | C19—O5—C20—C29 | −123.8 (3) |
C1—O2—C2—C3 | −13.4 (4) | C19—O5—C20—C21 | 0.8 (3) |
O2—C2—C3—N1 | 16.7 (4) | O5—C20—C21—N2 | −2.7 (3) |
C11—C2—C3—N1 | −103.9 (4) | C29—C20—C21—N2 | 117.5 (3) |
O2—C2—C3—C4 | 138.2 (4) | O5—C20—C21—C22 | −125.3 (3) |
C11—C2—C3—C4 | 17.6 (5) | C29—C20—C21—C22 | −5.1 (4) |
O1—C1—N1—C3 | −172.0 (4) | O4—C19—N2—C21 | 178.1 (4) |
O2—C1—N1—C3 | 8.5 (4) | O5—C19—N2—C21 | −3.9 (4) |
C4—C3—N1—C1 | −138.5 (4) | C22—C21—N2—C19 | 127.8 (3) |
C2—C3—N1—C1 | −15.8 (4) | C20—C21—N2—C19 | 4.0 (4) |
N1—C3—C4—C5 | −63.7 (5) | N2—C21—C22—C23 | 79.4 (4) |
C2—C3—C4—C5 | −177.5 (4) | C20—C21—C22—C23 | −166.1 (3) |
C3—C4—C5—C6 | −89.5 (5) | C21—C22—C23—C28 | 115.3 (4) |
C3—C4—C5—C10 | 90.1 (5) | C21—C22—C23—C24 | −66.9 (5) |
C10—C5—C6—C7 | 1.9 (7) | C28—C23—C24—C25 | 0.7 (5) |
C4—C5—C6—C7 | −178.5 (4) | C22—C23—C24—C25 | −177.1 (3) |
C5—C6—C7—C8 | −0.1 (8) | C23—C24—C25—C26 | 1.1 (5) |
C6—C7—C8—C9 | −1.9 (8) | C24—C25—C26—C27 | −1.9 (5) |
C7—C8—C9—C10 | 2.0 (7) | C25—C26—C27—C28 | 0.9 (6) |
C6—C5—C10—C9 | −1.7 (7) | C26—C27—C28—C23 | 0.9 (5) |
C4—C5—C10—C9 | 178.7 (4) | C24—C23—C28—C27 | −1.7 (5) |
C8—C9—C10—C5 | −0.2 (7) | C22—C23—C28—C27 | 176.2 (3) |
O2—C2—C11—O3 | 152.9 (4) | O5—C20—C29—O6 | −152.7 (3) |
C3—C2—C11—O3 | −89.5 (5) | C21—C20—C29—O6 | 88.6 (4) |
O2—C2—C11—S1 | −27.7 (4) | O5—C20—C29—S2 | 28.2 (3) |
C3—C2—C11—S1 | 89.9 (3) | C21—C20—C29—S2 | −90.5 (3) |
O3—C11—S1—C12 | 3.0 (4) | O6—C29—S2—C30 | −4.4 (4) |
C2—C11—S1—C12 | −176.4 (3) | C20—C29—S2—C30 | 174.7 (2) |
C11—S1—C12—C13 | 124.0 (3) | C29—S2—C30—C35 | 121.9 (3) |
C11—S1—C12—C17 | −65.7 (4) | C29—S2—C30—C31 | −60.9 (3) |
C17—C12—C13—C14 | −2.6 (6) | C35—C30—C31—C32 | −0.7 (5) |
S1—C12—C13—C14 | 167.8 (3) | S2—C30—C31—C32 | −177.8 (3) |
C12—C13—C14—C15 | 0.4 (6) | C30—C31—C32—C33 | 1.3 (6) |
C13—C14—C15—C16 | 2.4 (6) | C31—C32—C33—C34 | −1.2 (6) |
C13—C14—C15—C18 | −175.4 (4) | C31—C32—C33—C36 | 179.6 (4) |
C14—C15—C16—C17 | −3.2 (7) | C32—C33—C34—C35 | 0.5 (5) |
C18—C15—C16—C17 | 174.6 (4) | C36—C33—C34—C35 | 179.7 (3) |
C13—C12—C17—C16 | 1.8 (7) | C31—C30—C35—C34 | 0.0 (5) |
S1—C12—C17—C16 | −168.3 (4) | S2—C30—C35—C34 | 177.2 (3) |
C15—C16—C17—C12 | 1.2 (7) | C33—C34—C35—C30 | 0.1 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.79 (4) | 2.12 (4) | 2.900 (4) | 168 (4) |
N2—H2···O4ii | 0.78 (3) | 2.09 (3) | 2.853 (3) | 167 (4) |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1, −y+1, −z+1. |