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
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. |