organic compounds
The title compound, C17H15NO3S, 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, both with a slightly twisted heterocyclic ring. N—HO=C hydrogen bonds link the molecules together into centrosymmetric sets of four.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802010723/bt6152sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802010723/bt6152Isup2.hkl |
CCDC reference: 189903
Computing details top
Data collection: SMART (Siemens, 1995); cell refinement: Siemens SMART; 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-Phenyl-5-(4-tolylthiocarbonyl)oxazolidin-2-one top
Crystal data top
C17H15NO3S | Z = 4 |
Mr = 313.36 | F(000) = 656 |
Triclinic, P1 | Dx = 1.344 Mg m−3 |
a = 8.931 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.854 (5) Å | Cell parameters from 68 reflections |
c = 14.884 (4) Å | θ = 1.5–23.0° |
α = 75.067 (18)° | µ = 0.22 mm−1 |
β = 72.757 (14)° | T = 160 K |
γ = 75.547 (15)° | Block, colourless |
V = 1548.7 (9) Å3 | 0.78 × 0.74 × 0.70 mm |
Data collection top
Siemens SMART 1K CCD diffractometer | 4723 independent reflections |
Radiation source: sealed tube | 4468 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 8.192 pixels mm-1 | θmax = 25.2°, θmin = 1.5° |
ω rotation with narrow frames scans | h = −7→10 |
Absorption correction: multi-scan (XPREP in SHELXTL; Sheldrick, 1994) | k = −15→12 |
Tmin = 0.814, Tmax = 0.950 | l = −17→17 |
6481 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)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0536P)2 + 0.8478P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.003 |
4723 reflections | Δρmax = 0.65 e Å−3 |
406 parameters | Δρmin = −0.25 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: 0.0111 (15) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.28985 (17) | 0.56163 (12) | 1.05274 (11) | 0.0451 (4) | |
C1 | 0.3180 (2) | 0.61817 (15) | 0.97183 (15) | 0.0358 (5) | |
N1 | 0.4494 (2) | 0.60768 (14) | 0.90180 (12) | 0.0391 (4) | |
H1 | 0.526 (3) | 0.559 (2) | 0.9056 (17) | 0.047* | |
C2 | 0.4385 (2) | 0.68283 (15) | 0.81164 (14) | 0.0343 (4) | |
H2A | 0.4229 | 0.6423 | 0.7671 | 0.041* | |
C3 | 0.2773 (2) | 0.76061 (16) | 0.84776 (14) | 0.0340 (4) | |
H3 | 0.2046 | 0.7671 | 0.8061 | 0.041* | |
O2 | 0.20927 (15) | 0.70543 (11) | 0.94370 (10) | 0.0363 (3) | |
C5 | 0.5864 (2) | 0.73263 (15) | 0.76410 (13) | 0.0320 (4) | |
C6 | 0.6550 (2) | 0.73596 (16) | 0.66652 (14) | 0.0388 (5) | |
H6 | 0.6065 | 0.7093 | 0.6303 | 0.047* | |
C7 | 0.7935 (3) | 0.77799 (18) | 0.62183 (17) | 0.0498 (6) | |
H7 | 0.8403 | 0.7793 | 0.5554 | 0.060* | |
C8 | 0.8630 (3) | 0.81771 (18) | 0.67370 (19) | 0.0551 (6) | |
H8 | 0.9567 | 0.8477 | 0.6428 | 0.066* | |
C9 | 0.7968 (3) | 0.81419 (18) | 0.77073 (19) | 0.0494 (6) | |
H9 | 0.8453 | 0.8417 | 0.8063 | 0.059* | |
C10 | 0.6596 (2) | 0.77063 (17) | 0.81646 (15) | 0.0387 (5) | |
H10 | 0.6159 | 0.7668 | 0.8834 | 0.046* | |
C4 | 0.2943 (2) | 0.87516 (16) | 0.84913 (14) | 0.0326 (4) | |
O3 | 0.32182 (17) | 0.94177 (11) | 0.77568 (10) | 0.0402 (3) | |
S1 | 0.27086 (6) | 0.89610 (4) | 0.96645 (4) | 0.03890 (16) | |
C11 | 0.3068 (2) | 1.03196 (16) | 0.94028 (14) | 0.0362 (4) | |
C12 | 0.1883 (3) | 1.11083 (19) | 0.98022 (17) | 0.0461 (5) | |
H12 | 0.0883 | 1.0929 | 1.0175 | 0.055* | |
C13 | 0.2150 (3) | 1.21643 (19) | 0.96610 (18) | 0.0509 (6) | |
H13 | 0.1331 | 1.2701 | 0.9944 | 0.061* | |
C14 | 0.3597 (3) | 1.24455 (17) | 0.91127 (16) | 0.0461 (5) | |
C15 | 0.4771 (3) | 1.16452 (18) | 0.87126 (16) | 0.0460 (5) | |
H15 | 0.5765 | 1.1828 | 0.8330 | 0.055* | |
C16 | 0.4528 (3) | 1.05842 (18) | 0.88582 (15) | 0.0423 (5) | |
H16 | 0.5353 | 1.0043 | 0.8587 | 0.051* | |
C17 | 0.3897 (4) | 1.3591 (2) | 0.8960 (2) | 0.0643 (7) | |
H17A | 0.3326 | 1.4086 | 0.8497 | 0.096* | |
H17B | 0.5044 | 1.3589 | 0.8712 | 0.096* | |
H17C | 0.3516 | 1.3841 | 0.9571 | 0.096* | |
O4 | 0.1110 (2) | 0.59694 (13) | 0.81705 (12) | 0.0508 (4) | |
C18 | 0.0686 (2) | 0.55830 (16) | 0.76494 (15) | 0.0365 (5) | |
N2 | −0.0374 (2) | 0.49307 (15) | 0.78628 (13) | 0.0412 (4) | |
H2 | −0.095 (3) | 0.480 (2) | 0.8403 (18) | 0.049* | |
C19 | −0.0699 (2) | 0.47179 (16) | 0.70356 (13) | 0.0333 (4) | |
H19 | −0.1740 | 0.5184 | 0.6940 | 0.040* | |
C20 | 0.0694 (2) | 0.51803 (16) | 0.62296 (14) | 0.0352 (4) | |
H20 | 0.0249 | 0.5701 | 0.5704 | 0.042* | |
O5 | 0.13334 (16) | 0.57698 (11) | 0.66783 (10) | 0.0390 (3) | |
C22 | −0.0756 (2) | 0.35299 (16) | 0.71130 (13) | 0.0318 (4) | |
C23 | −0.1580 (2) | 0.32791 (18) | 0.65604 (15) | 0.0403 (5) | |
H23 | −0.2130 | 0.3853 | 0.6162 | 0.048* | |
C24 | −0.1604 (3) | 0.21945 (19) | 0.65875 (17) | 0.0462 (5) | |
H24 | −0.2151 | 0.2029 | 0.6199 | 0.055* | |
C25 | −0.0834 (3) | 0.13564 (18) | 0.71794 (17) | 0.0468 (5) | |
H25 | −0.0857 | 0.0615 | 0.7202 | 0.056* | |
C26 | −0.0026 (3) | 0.16031 (17) | 0.77393 (17) | 0.0460 (5) | |
H26 | 0.0499 | 0.1030 | 0.8150 | 0.055* | |
C27 | 0.0017 (2) | 0.26823 (17) | 0.77016 (15) | 0.0395 (5) | |
H27 | 0.0582 | 0.2844 | 0.8083 | 0.047* | |
C21 | 0.2002 (2) | 0.42980 (16) | 0.58084 (13) | 0.0350 (4) | |
O6 | 0.19195 (17) | 0.39438 (13) | 0.51557 (10) | 0.0459 (4) | |
S2 | 0.35965 (6) | 0.38545 (4) | 0.63860 (4) | 0.03778 (16) | |
C28 | 0.4747 (2) | 0.27834 (16) | 0.57799 (14) | 0.0341 (4) | |
C29 | 0.4622 (2) | 0.16979 (16) | 0.62086 (14) | 0.0373 (5) | |
H29 | 0.3879 | 0.1528 | 0.6807 | 0.045* | |
C30 | 0.5600 (2) | 0.08700 (16) | 0.57485 (15) | 0.0379 (5) | |
H30 | 0.5521 | 0.0129 | 0.6038 | 0.045* | |
C31 | 0.6697 (2) | 0.11003 (16) | 0.48700 (14) | 0.0345 (4) | |
C32 | 0.6784 (2) | 0.21907 (16) | 0.44548 (14) | 0.0354 (4) | |
H32 | 0.7514 | 0.2363 | 0.3852 | 0.043* | |
C33 | 0.5827 (2) | 0.30298 (16) | 0.49049 (14) | 0.0365 (4) | |
H33 | 0.5909 | 0.3771 | 0.4616 | 0.044* | |
C34 | 0.7777 (3) | 0.01949 (17) | 0.43826 (16) | 0.0416 (5) | |
H34A | 0.7259 | −0.0444 | 0.4571 | 0.062* | |
H34B | 0.8786 | −0.0009 | 0.4575 | 0.062* | |
H34C | 0.7987 | 0.0449 | 0.3685 | 0.062* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0403 (8) | 0.0366 (8) | 0.0459 (9) | −0.0092 (6) | 0.0029 (6) | −0.0003 (7) |
C1 | 0.0341 (10) | 0.0272 (10) | 0.0451 (12) | −0.0106 (8) | −0.0030 (9) | −0.0089 (9) |
N1 | 0.0358 (9) | 0.0283 (9) | 0.0423 (10) | −0.0039 (7) | 0.0017 (8) | −0.0036 (7) |
C2 | 0.0380 (11) | 0.0318 (10) | 0.0360 (10) | −0.0102 (8) | −0.0066 (8) | −0.0111 (8) |
C3 | 0.0322 (10) | 0.0375 (10) | 0.0355 (10) | −0.0103 (8) | −0.0093 (8) | −0.0083 (8) |
O2 | 0.0304 (7) | 0.0355 (7) | 0.0416 (8) | −0.0092 (6) | −0.0036 (6) | −0.0083 (6) |
C5 | 0.0310 (10) | 0.0271 (9) | 0.0358 (10) | −0.0040 (8) | −0.0066 (8) | −0.0059 (8) |
C6 | 0.0412 (11) | 0.0326 (10) | 0.0354 (11) | 0.0007 (9) | −0.0068 (9) | −0.0050 (8) |
C7 | 0.0450 (13) | 0.0370 (11) | 0.0470 (13) | −0.0002 (10) | 0.0065 (10) | −0.0010 (10) |
C8 | 0.0333 (11) | 0.0377 (12) | 0.0783 (17) | −0.0082 (9) | 0.0038 (11) | −0.0033 (12) |
C9 | 0.0371 (12) | 0.0414 (12) | 0.0735 (16) | −0.0099 (9) | −0.0156 (11) | −0.0134 (11) |
C10 | 0.0363 (11) | 0.0381 (11) | 0.0428 (11) | −0.0076 (9) | −0.0096 (9) | −0.0098 (9) |
C4 | 0.0285 (9) | 0.0334 (10) | 0.0378 (11) | −0.0040 (8) | −0.0109 (8) | −0.0093 (9) |
O3 | 0.0486 (8) | 0.0346 (7) | 0.0386 (8) | −0.0057 (6) | −0.0155 (6) | −0.0057 (6) |
S1 | 0.0458 (3) | 0.0400 (3) | 0.0349 (3) | −0.0148 (2) | −0.0076 (2) | −0.0107 (2) |
C11 | 0.0397 (11) | 0.0389 (11) | 0.0364 (10) | −0.0092 (9) | −0.0147 (9) | −0.0108 (8) |
C12 | 0.0378 (11) | 0.0528 (13) | 0.0554 (13) | −0.0063 (10) | −0.0132 (10) | −0.0244 (11) |
C13 | 0.0511 (14) | 0.0459 (13) | 0.0669 (15) | 0.0034 (10) | −0.0270 (12) | −0.0279 (11) |
C14 | 0.0655 (15) | 0.0383 (12) | 0.0474 (12) | −0.0094 (10) | −0.0331 (11) | −0.0091 (10) |
C15 | 0.0546 (13) | 0.0471 (13) | 0.0440 (12) | −0.0209 (11) | −0.0144 (10) | −0.0087 (10) |
C16 | 0.0428 (12) | 0.0420 (12) | 0.0451 (12) | −0.0088 (9) | −0.0096 (9) | −0.0145 (9) |
C17 | 0.101 (2) | 0.0412 (13) | 0.0676 (16) | −0.0178 (13) | −0.0426 (16) | −0.0098 (12) |
O4 | 0.0574 (10) | 0.0455 (9) | 0.0612 (10) | −0.0147 (7) | −0.0187 (8) | −0.0212 (8) |
C18 | 0.0357 (11) | 0.0308 (10) | 0.0434 (11) | −0.0067 (8) | −0.0074 (9) | −0.0105 (9) |
N2 | 0.0484 (11) | 0.0454 (10) | 0.0320 (9) | −0.0228 (8) | 0.0041 (8) | −0.0143 (8) |
C19 | 0.0288 (10) | 0.0348 (10) | 0.0360 (10) | −0.0048 (8) | −0.0057 (8) | −0.0103 (8) |
C20 | 0.0371 (11) | 0.0331 (10) | 0.0321 (10) | −0.0045 (8) | −0.0067 (8) | −0.0048 (8) |
O5 | 0.0393 (8) | 0.0319 (7) | 0.0425 (8) | −0.0126 (6) | 0.0012 (6) | −0.0091 (6) |
C22 | 0.0270 (9) | 0.0349 (10) | 0.0342 (10) | −0.0064 (8) | −0.0042 (8) | −0.0114 (8) |
C23 | 0.0375 (11) | 0.0448 (12) | 0.0425 (11) | −0.0080 (9) | −0.0146 (9) | −0.0094 (9) |
C24 | 0.0446 (12) | 0.0497 (13) | 0.0545 (13) | −0.0141 (10) | −0.0141 (10) | −0.0206 (11) |
C25 | 0.0410 (12) | 0.0376 (11) | 0.0628 (14) | −0.0091 (9) | −0.0036 (10) | −0.0208 (10) |
C26 | 0.0445 (12) | 0.0349 (11) | 0.0558 (13) | −0.0019 (9) | −0.0152 (10) | −0.0061 (10) |
C27 | 0.0371 (11) | 0.0403 (11) | 0.0446 (12) | −0.0054 (9) | −0.0153 (9) | −0.0103 (9) |
C21 | 0.0347 (10) | 0.0350 (10) | 0.0299 (10) | −0.0056 (8) | −0.0040 (8) | −0.0026 (8) |
O6 | 0.0424 (8) | 0.0592 (10) | 0.0351 (8) | 0.0040 (7) | −0.0111 (6) | −0.0191 (7) |
S2 | 0.0343 (3) | 0.0392 (3) | 0.0408 (3) | −0.0027 (2) | −0.0099 (2) | −0.0130 (2) |
C28 | 0.0303 (10) | 0.0346 (10) | 0.0392 (11) | −0.0049 (8) | −0.0118 (8) | −0.0076 (8) |
C29 | 0.0337 (10) | 0.0388 (11) | 0.0379 (11) | −0.0109 (9) | −0.0066 (8) | −0.0036 (9) |
C30 | 0.0376 (11) | 0.0326 (10) | 0.0440 (11) | −0.0102 (8) | −0.0113 (9) | −0.0034 (9) |
C31 | 0.0308 (10) | 0.0358 (10) | 0.0403 (11) | −0.0051 (8) | −0.0133 (8) | −0.0094 (8) |
C32 | 0.0313 (10) | 0.0366 (11) | 0.0349 (10) | −0.0074 (8) | −0.0051 (8) | −0.0038 (8) |
C33 | 0.0340 (10) | 0.0319 (10) | 0.0413 (11) | −0.0068 (8) | −0.0087 (9) | −0.0035 (8) |
C34 | 0.0423 (12) | 0.0374 (11) | 0.0465 (12) | −0.0033 (9) | −0.0127 (9) | −0.0130 (9) |
Geometric parameters (Å, º) top
O1—C1 | 1.226 (2) | O4—C18 | 1.207 (2) |
C1—N1 | 1.323 (3) | C18—N2 | 1.335 (3) |
C1—O2 | 1.353 (2) | C18—O5 | 1.370 (2) |
N1—H1 | 0.80 (3) | N2—H2 | 0.82 (3) |
N1—C2 | 1.451 (3) | N2—C19 | 1.449 (3) |
C2—H2A | 1.000 | C19—H19 | 1.000 |
C2—C3 | 1.569 (3) | C19—C20 | 1.568 (3) |
C2—C5 | 1.513 (3) | C19—C22 | 1.514 (3) |
C3—H3 | 1.000 | C20—H20 | 1.000 |
C3—O2 | 1.446 (2) | C20—O5 | 1.431 (2) |
C3—C4 | 1.523 (3) | C20—C21 | 1.521 (3) |
C5—C6 | 1.393 (3) | C22—C23 | 1.392 (3) |
C5—C10 | 1.390 (3) | C22—C27 | 1.386 (3) |
C6—H6 | 0.950 | C23—H23 | 0.950 |
C6—C7 | 1.388 (3) | C23—C24 | 1.390 (3) |
C7—H7 | 0.950 | C24—H24 | 0.950 |
C7—C8 | 1.374 (4) | C24—C25 | 1.382 (3) |
C8—H8 | 0.950 | C25—H25 | 0.950 |
C8—C9 | 1.382 (4) | C25—C26 | 1.386 (3) |
C9—H9 | 0.950 | C26—H26 | 0.950 |
C9—C10 | 1.389 (3) | C26—C27 | 1.384 (3) |
C10—H10 | 0.950 | C27—H27 | 0.950 |
C4—O3 | 1.205 (2) | C21—O6 | 1.202 (2) |
C4—S1 | 1.778 (2) | C21—S2 | 1.777 (2) |
S1—C11 | 1.778 (2) | S2—C28 | 1.775 (2) |
C11—C12 | 1.379 (3) | C28—C29 | 1.394 (3) |
C11—C16 | 1.388 (3) | C28—C33 | 1.386 (3) |
C12—H12 | 0.950 | C29—H29 | 0.950 |
C12—C13 | 1.388 (3) | C29—C30 | 1.386 (3) |
C13—H13 | 0.950 | C30—H30 | 0.950 |
C13—C14 | 1.386 (4) | C30—C31 | 1.394 (3) |
C14—C15 | 1.386 (3) | C31—C32 | 1.390 (3) |
C14—C17 | 1.509 (3) | C31—C34 | 1.507 (3) |
C15—H15 | 0.950 | C32—H32 | 0.950 |
C15—C16 | 1.386 (3) | C32—C33 | 1.384 (3) |
C16—H16 | 0.950 | C33—H33 | 0.950 |
C17—H17A | 0.980 | C34—H34A | 0.980 |
C17—H17B | 0.980 | C34—H34B | 0.980 |
C17—H17C | 0.980 | C34—H34C | 0.980 |
O1—C1—N1 | 128.36 (19) | O4—C18—N2 | 129.9 (2) |
O1—C1—O2 | 121.18 (18) | O4—C18—O5 | 121.13 (18) |
N1—C1—O2 | 110.45 (17) | N2—C18—O5 | 108.94 (17) |
C1—N1—H1 | 123.9 (17) | C18—N2—H2 | 121.5 (17) |
C1—N1—C2 | 114.33 (18) | C18—N2—C19 | 114.44 (17) |
H1—N1—C2 | 121.3 (18) | H2—N2—C19 | 122.2 (17) |
N1—C2—H2A | 108.8 | N2—C19—H19 | 109.0 |
N1—C2—C3 | 99.05 (15) | N2—C19—C20 | 99.39 (15) |
N1—C2—C5 | 112.49 (16) | N2—C19—C22 | 113.92 (16) |
H2A—C2—C3 | 108.8 | H19—C19—C20 | 109.0 |
H2A—C2—C5 | 108.8 | H19—C19—C22 | 109.0 |
C3—C2—C5 | 118.24 (16) | C20—C19—C22 | 116.00 (15) |
C2—C3—H3 | 108.8 | C19—C20—H20 | 109.2 |
C2—C3—O2 | 105.35 (15) | C19—C20—O5 | 105.26 (15) |
C2—C3—C4 | 114.71 (15) | C19—C20—C21 | 113.75 (16) |
H3—C3—O2 | 108.8 | H20—C20—O5 | 109.2 |
H3—C3—C4 | 108.8 | H20—C20—C21 | 109.2 |
O2—C3—C4 | 110.16 (15) | O5—C20—C21 | 110.00 (16) |
C1—O2—C3 | 109.34 (15) | C18—O5—C20 | 110.33 (14) |
C2—C5—C6 | 119.30 (18) | C19—C22—C23 | 118.98 (17) |
C2—C5—C10 | 121.47 (17) | C19—C22—C27 | 122.04 (17) |
C6—C5—C10 | 119.16 (19) | C23—C22—C27 | 118.96 (18) |
C5—C6—H6 | 119.8 | C22—C23—H23 | 119.8 |
C5—C6—C7 | 120.5 (2) | C22—C23—C24 | 120.4 (2) |
H6—C6—C7 | 119.8 | H23—C23—C24 | 119.8 |
C6—C7—H7 | 120.0 | C23—C24—H24 | 119.9 |
C6—C7—C8 | 120.0 (2) | C23—C24—C25 | 120.1 (2) |
H7—C7—C8 | 120.0 | H24—C24—C25 | 119.9 |
C7—C8—H8 | 119.9 | C24—C25—H25 | 120.2 |
C7—C8—C9 | 120.2 (2) | C24—C25—C26 | 119.7 (2) |
H8—C8—C9 | 119.9 | H25—C25—C26 | 120.2 |
C8—C9—H9 | 119.8 | C25—C26—H26 | 119.9 |
C8—C9—C10 | 120.3 (2) | C25—C26—C27 | 120.2 (2) |
H9—C9—C10 | 119.8 | H26—C26—C27 | 119.9 |
C5—C10—C9 | 119.9 (2) | C22—C27—C26 | 120.65 (19) |
C5—C10—H10 | 120.0 | C22—C27—H27 | 119.7 |
C9—C10—H10 | 120.0 | C26—C27—H27 | 119.7 |
C3—C4—O3 | 120.83 (17) | C20—C21—O6 | 121.75 (18) |
C3—C4—S1 | 113.37 (14) | C20—C21—S2 | 113.43 (14) |
O3—C4—S1 | 125.80 (15) | O6—C21—S2 | 124.81 (16) |
C4—S1—C11 | 100.98 (9) | C21—S2—C28 | 99.96 (9) |
S1—C11—C12 | 118.35 (16) | S2—C28—C29 | 119.91 (15) |
S1—C11—C16 | 121.73 (16) | S2—C28—C33 | 119.56 (15) |
C12—C11—C16 | 119.8 (2) | C29—C28—C33 | 120.45 (18) |
C11—C12—H12 | 119.9 | C28—C29—H29 | 120.5 |
C11—C12—C13 | 120.2 (2) | C28—C29—C30 | 118.95 (18) |
H12—C12—C13 | 119.9 | H29—C29—C30 | 120.5 |
C12—C13—H13 | 119.6 | C29—C30—H30 | 119.3 |
C12—C13—C14 | 120.8 (2) | C29—C30—C31 | 121.49 (18) |
H13—C13—C14 | 119.6 | H30—C30—C31 | 119.3 |
C13—C14—C15 | 118.3 (2) | C30—C31—C32 | 118.30 (18) |
C13—C14—C17 | 121.1 (2) | C30—C31—C34 | 121.19 (18) |
C15—C14—C17 | 120.6 (2) | C32—C31—C34 | 120.51 (18) |
C14—C15—H15 | 119.3 | C31—C32—H32 | 119.4 |
C14—C15—C16 | 121.5 (2) | C31—C32—C33 | 121.15 (18) |
H15—C15—C16 | 119.3 | H32—C32—C33 | 119.4 |
C11—C16—C15 | 119.4 (2) | C28—C33—C32 | 119.66 (18) |
C11—C16—H16 | 120.3 | C28—C33—H33 | 120.2 |
C15—C16—H16 | 120.3 | C32—C33—H33 | 120.2 |
C14—C17—H17A | 109.5 | C31—C34—H34A | 109.5 |
C14—C17—H17B | 109.5 | C31—C34—H34B | 109.5 |
C14—C17—H17C | 109.5 | C31—C34—H34C | 109.5 |
H17A—C17—H17B | 109.5 | H34A—C34—H34B | 109.5 |
H17A—C17—H17C | 109.5 | H34A—C34—H34C | 109.5 |
H17B—C17—H17C | 109.5 | H34B—C34—H34C | 109.5 |
O1—C1—N1—C2 | 174.83 (19) | O4—C18—N2—C19 | 174.0 (2) |
O2—C1—N1—C2 | −6.1 (2) | O5—C18—N2—C19 | −7.3 (2) |
C1—N1—C2—C3 | 11.0 (2) | C18—N2—C19—C20 | 12.0 (2) |
C1—N1—C2—C5 | 136.75 (18) | C18—N2—C19—C22 | 136.04 (18) |
N1—C2—C3—O2 | −11.54 (17) | N2—C19—C20—O5 | −11.96 (18) |
N1—C2—C3—C4 | 109.77 (17) | N2—C19—C20—C21 | 108.52 (18) |
C5—C2—C3—O2 | −133.23 (17) | C22—C19—C20—O5 | −134.50 (16) |
C5—C2—C3—C4 | −11.9 (2) | C22—C19—C20—C21 | −14.0 (2) |
O1—C1—O2—C3 | 176.50 (17) | O4—C18—O5—C20 | 177.07 (18) |
N1—C1—O2—C3 | −2.7 (2) | N2—C18—O5—C20 | −1.8 (2) |
C2—C3—O2—C1 | 9.32 (19) | C19—C20—O5—C18 | 9.0 (2) |
C4—C3—O2—C1 | −114.91 (17) | C21—C20—O5—C18 | −113.88 (17) |
N1—C2—C5—C6 | 133.50 (19) | N2—C19—C22—C23 | 157.66 (18) |
N1—C2—C5—C10 | −43.5 (2) | N2—C19—C22—C27 | −23.8 (3) |
C3—C2—C5—C6 | −111.9 (2) | C20—C19—C22—C23 | −87.8 (2) |
C3—C2—C5—C10 | 71.0 (2) | C20—C19—C22—C27 | 90.7 (2) |
C2—C5—C6—C7 | −177.92 (18) | C19—C22—C23—C24 | 177.56 (19) |
C10—C5—C6—C7 | −0.8 (3) | C27—C22—C23—C24 | −1.0 (3) |
C5—C6—C7—C8 | −0.7 (3) | C22—C23—C24—C25 | 1.3 (3) |
C6—C7—C8—C9 | 1.1 (3) | C23—C24—C25—C26 | −0.5 (3) |
C7—C8—C9—C10 | −0.1 (3) | C24—C25—C26—C27 | −0.4 (3) |
C8—C9—C10—C5 | −1.5 (3) | C25—C26—C27—C22 | 0.6 (3) |
C2—C5—C10—C9 | 178.92 (18) | C19—C22—C27—C26 | −178.46 (19) |
C6—C5—C10—C9 | 1.9 (3) | C23—C22—C27—C26 | 0.1 (3) |
C2—C3—C4—O3 | 74.5 (2) | C19—C20—C21—O6 | 86.5 (2) |
C2—C3—C4—S1 | −105.10 (16) | C19—C20—C21—S2 | −92.65 (18) |
O2—C3—C4—O3 | −166.88 (17) | O5—C20—C21—O6 | −155.69 (18) |
O2—C3—C4—S1 | 13.55 (19) | O5—C20—C21—S2 | 25.13 (19) |
C3—C4—S1—C11 | 177.37 (13) | C20—C21—S2—C28 | 175.37 (14) |
O3—C4—S1—C11 | −2.2 (2) | O6—C21—S2—C28 | −3.8 (2) |
C4—S1—C11—C12 | 121.24 (17) | C21—S2—C28—C29 | −98.96 (17) |
C4—S1—C11—C16 | −62.48 (18) | C21—S2—C28—C33 | 84.43 (17) |
S1—C11—C12—C13 | 176.29 (17) | S2—C28—C29—C30 | −176.23 (15) |
C16—C11—C12—C13 | −0.1 (3) | C33—C28—C29—C30 | 0.4 (3) |
C11—C12—C13—C14 | 0.6 (3) | C28—C29—C30—C31 | −0.1 (3) |
C12—C13—C14—C15 | −0.2 (3) | C29—C30—C31—C32 | −0.5 (3) |
C12—C13—C14—C17 | −179.7 (2) | C29—C30—C31—C34 | 178.91 (18) |
C13—C14—C15—C16 | −0.6 (3) | C30—C31—C32—C33 | 0.9 (3) |
C17—C14—C15—C16 | 178.9 (2) | C34—C31—C32—C33 | −178.48 (18) |
C14—C15—C16—C11 | 1.1 (3) | C31—C32—C33—C28 | −0.7 (3) |
S1—C11—C16—C15 | −176.98 (16) | S2—C28—C33—C32 | 176.66 (15) |
C12—C11—C16—C15 | −0.8 (3) | C29—C28—C33—C32 | 0.1 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.80 (3) | 2.08 (3) | 2.874 (3) | 167 (2) |
N2—H2···O1ii | 0.82 (3) | 2.06 (3) | 2.835 (2) | 159 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x, −y+1, −z+2. |