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
Key indicators
- Single-crystal X-ray study
- T = 160 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.108
- Data-to-parameter ratio = 11.6
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level A:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.20 From the CIF: _reflns_number_total 4723 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 5589 Completeness (_total/calc) 84.51% Alert A: < 85% complete (theta max?)
Alert Level B:
CRYSS_02 Alert B The value of _exptl_crystal_size_min is > 0.6 Minimum crystal size given = 0.700
Author response: Cutting the crystals degraded their quality and that of the resulting diffraction pattern. |
Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.814 0.950 Tmin' and Tmax expected: 0.838 0.857 RR' = 0.876 Please check that your absorption correction is appropriate. 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 0.902 Tmax scaled 0.857 Tmin scaled 0.734
1 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
1 Alert Level C = Please check
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. |