In the title compound, C
29H
25NO
2S
2, the benzene rings of the phenylsulfonyl and the dimethylbenzyl substituents are almost perpendicular to the indole unit, whereas the dihedral angle between the phenyl rings of the phenylsulfanyl and phenylsulfonyl groups is 71.2 (1)°. The molecules in the crystal structure are held together by van der Waals, C—H
O and C—H
S interactions.
Supporting information
CCDC reference: 277206
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.003 Å
- R factor = 0.049
- wR factor = 0.143
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.68
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.78 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C26
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C27
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C28
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C25 -C30 1.37 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
7 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
2-(2,5-Dimethylbenzyl)-3-phenylsulfanyl-1-phenylsulfonyl-1
H-indole
top
Crystal data top
C29H25NO2S2 | F(000) = 1016 |
Mr = 483.62 | Dx = 1.352 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5656 reflections |
a = 10.8372 (6) Å | θ = 2.2–27.5° |
b = 17.2384 (10) Å | µ = 0.25 mm−1 |
c = 12.7220 (7) Å | T = 273 K |
β = 90.269 (1)° | Block, colourless |
V = 2376.6 (2) Å3 | 0.23 × 0.22 × 0.20 mm |
Z = 4 | |
Data collection top
CCD Area Detector diffractometer | 4227 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 28.0°, θmin = 2.0° |
ω scans | h = −14→14 |
14279 measured reflections | k = −22→21 |
5221 independent reflections | l = −14→16 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0882P)2 + 0.5156P] where P = (Fo2 + 2Fc2)/3 |
5221 reflections | (Δ/σ)max < 0.001 |
309 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Special details top
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. |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.19553 (4) | 0.14502 (3) | 0.40570 (4) | 0.04367 (15) | |
S2 | −0.12103 (5) | −0.09334 (3) | 0.29680 (5) | 0.05571 (18) | |
O1 | 0.26970 (14) | 0.09530 (9) | 0.46788 (12) | 0.0569 (4) | |
O2 | 0.15292 (15) | 0.21698 (9) | 0.44644 (12) | 0.0605 (4) | |
N1 | 0.06757 (13) | 0.09474 (9) | 0.37415 (13) | 0.0415 (4) | |
C2 | 0.05464 (16) | 0.01335 (10) | 0.36412 (14) | 0.0397 (4) | |
C3 | −0.05516 (17) | −0.00109 (11) | 0.31560 (15) | 0.0426 (4) | |
C4 | −0.11465 (16) | 0.07161 (11) | 0.29197 (16) | 0.0446 (4) | |
C5 | −0.03739 (17) | 0.13065 (11) | 0.32845 (15) | 0.0428 (4) | |
C6 | −0.06920 (19) | 0.20819 (12) | 0.31902 (18) | 0.0535 (5) | |
H6 | −0.0180 | 0.2472 | 0.3447 | 0.064* | |
C7 | −0.1799 (2) | 0.22535 (15) | 0.2700 (2) | 0.0678 (7) | |
H7 | −0.2032 | 0.2769 | 0.2620 | 0.081* | |
C8 | −0.2566 (2) | 0.16760 (16) | 0.2327 (2) | 0.0714 (7) | |
H8 | −0.3303 | 0.1811 | 0.1997 | 0.086* | |
C9 | −0.22640 (19) | 0.09054 (14) | 0.2434 (2) | 0.0591 (6) | |
H9 | −0.2792 | 0.0520 | 0.2189 | 0.071* | |
C10 | 0.26982 (16) | 0.16222 (10) | 0.28523 (16) | 0.0418 (4) | |
C11 | 0.2348 (2) | 0.22401 (12) | 0.22219 (18) | 0.0536 (5) | |
H11 | 0.1725 | 0.2575 | 0.2434 | 0.064* | |
C12 | 0.2936 (2) | 0.23505 (14) | 0.12778 (19) | 0.0625 (6) | |
H12 | 0.2692 | 0.2754 | 0.0838 | 0.075* | |
C13 | 0.3879 (2) | 0.18695 (14) | 0.0982 (2) | 0.0636 (6) | |
H13 | 0.4282 | 0.1955 | 0.0349 | 0.076* | |
C14 | 0.4234 (2) | 0.12618 (13) | 0.16139 (19) | 0.0563 (5) | |
H14 | 0.4869 | 0.0935 | 0.1403 | 0.068* | |
C15 | 0.36531 (17) | 0.11354 (12) | 0.25560 (17) | 0.0482 (5) | |
H15 | 0.3898 | 0.0728 | 0.2989 | 0.058* | |
C16 | 0.14267 (17) | −0.04500 (11) | 0.40864 (16) | 0.0448 (4) | |
H16A | 0.0988 | −0.0935 | 0.4183 | 0.054* | |
H16B | 0.1691 | −0.0273 | 0.4775 | 0.054* | |
C17 | 0.25687 (16) | −0.06079 (10) | 0.34289 (15) | 0.0400 (4) | |
C18 | 0.24802 (17) | −0.06038 (10) | 0.23419 (15) | 0.0427 (4) | |
H18 | 0.1719 | −0.0499 | 0.2032 | 0.051* | |
C19 | 0.34839 (19) | −0.07504 (11) | 0.16967 (17) | 0.0486 (5) | |
C20 | 0.46121 (19) | −0.08935 (12) | 0.2180 (2) | 0.0541 (5) | |
H20 | 0.5308 | −0.0976 | 0.1770 | 0.065* | |
C21 | 0.47140 (19) | −0.09154 (12) | 0.3258 (2) | 0.0544 (5) | |
H21 | 0.5478 | −0.1022 | 0.3560 | 0.065* | |
C22 | 0.37029 (18) | −0.07814 (11) | 0.39106 (17) | 0.0462 (4) | |
C23 | 0.3854 (2) | −0.08273 (15) | 0.50820 (19) | 0.0632 (6) | |
H23A | 0.3635 | −0.0338 | 0.5390 | 0.095* | |
H23B | 0.4698 | −0.0946 | 0.5251 | 0.095* | |
H23C | 0.3328 | −0.1227 | 0.5354 | 0.095* | |
C24 | 0.3344 (3) | −0.07449 (16) | 0.05237 (19) | 0.0696 (7) | |
H24A | 0.3912 | −0.0379 | 0.0227 | 0.104* | |
H24B | 0.2515 | −0.0599 | 0.0341 | 0.104* | |
H24C | 0.3514 | −0.1253 | 0.0252 | 0.104* | |
C25 | −0.07346 (18) | −0.11824 (11) | 0.16738 (17) | 0.0468 (4) | |
C26 | −0.1042 (4) | −0.07425 (17) | 0.0819 (2) | 0.0968 (11) | |
H26 | −0.1487 | −0.0286 | 0.0906 | 0.116* | |
C27 | −0.0695 (4) | −0.0974 (2) | −0.0170 (2) | 0.1101 (14) | |
H27 | −0.0910 | −0.0670 | −0.0746 | 0.132* | |
C28 | −0.0057 (3) | −0.16242 (17) | −0.0322 (2) | 0.0750 (7) | |
H28 | 0.0185 | −0.1766 | −0.0996 | 0.090* | |
C29 | 0.0238 (3) | −0.20780 (18) | 0.0513 (2) | 0.0786 (8) | |
H29 | 0.0669 | −0.2538 | 0.0410 | 0.094* | |
C30 | −0.0100 (2) | −0.18578 (14) | 0.1515 (2) | 0.0658 (6) | |
H30 | 0.0105 | −0.2171 | 0.2085 | 0.079* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0436 (3) | 0.0471 (3) | 0.0404 (3) | −0.00085 (18) | 0.00129 (18) | −0.00724 (19) |
S2 | 0.0593 (3) | 0.0512 (3) | 0.0567 (4) | −0.0143 (2) | 0.0101 (2) | −0.0014 (2) |
O1 | 0.0565 (8) | 0.0673 (9) | 0.0469 (9) | 0.0017 (7) | −0.0078 (7) | −0.0018 (7) |
O2 | 0.0655 (9) | 0.0563 (9) | 0.0596 (10) | −0.0008 (7) | 0.0057 (7) | −0.0192 (7) |
N1 | 0.0378 (8) | 0.0430 (8) | 0.0437 (9) | 0.0016 (6) | 0.0034 (6) | −0.0036 (6) |
C2 | 0.0413 (9) | 0.0423 (9) | 0.0357 (10) | 0.0013 (7) | 0.0109 (7) | −0.0005 (7) |
C3 | 0.0407 (9) | 0.0448 (9) | 0.0424 (11) | −0.0015 (7) | 0.0084 (8) | −0.0016 (8) |
C4 | 0.0395 (9) | 0.0482 (10) | 0.0462 (11) | 0.0023 (7) | 0.0070 (8) | −0.0026 (8) |
C5 | 0.0383 (9) | 0.0482 (10) | 0.0421 (11) | 0.0055 (7) | 0.0073 (7) | −0.0036 (8) |
C6 | 0.0489 (11) | 0.0478 (11) | 0.0640 (14) | 0.0086 (8) | 0.0057 (10) | −0.0065 (9) |
C7 | 0.0552 (13) | 0.0574 (13) | 0.0907 (19) | 0.0189 (10) | −0.0007 (12) | −0.0024 (12) |
C8 | 0.0472 (12) | 0.0772 (16) | 0.090 (2) | 0.0193 (11) | −0.0096 (12) | −0.0045 (14) |
C9 | 0.0420 (10) | 0.0645 (13) | 0.0709 (16) | 0.0040 (9) | −0.0024 (10) | −0.0065 (11) |
C10 | 0.0400 (9) | 0.0417 (9) | 0.0438 (11) | −0.0036 (7) | 0.0011 (7) | −0.0045 (7) |
C11 | 0.0554 (12) | 0.0454 (10) | 0.0602 (14) | 0.0054 (9) | 0.0060 (10) | 0.0006 (9) |
C12 | 0.0760 (15) | 0.0526 (12) | 0.0588 (15) | 0.0024 (10) | 0.0085 (12) | 0.0112 (10) |
C13 | 0.0728 (15) | 0.0594 (13) | 0.0588 (15) | −0.0029 (11) | 0.0209 (11) | 0.0027 (11) |
C14 | 0.0535 (12) | 0.0524 (11) | 0.0632 (14) | 0.0011 (9) | 0.0186 (10) | −0.0012 (10) |
C15 | 0.0423 (9) | 0.0444 (10) | 0.0579 (13) | −0.0007 (8) | 0.0042 (8) | 0.0005 (9) |
C16 | 0.0488 (10) | 0.0456 (10) | 0.0399 (11) | 0.0045 (8) | 0.0060 (8) | 0.0044 (8) |
C17 | 0.0428 (9) | 0.0357 (8) | 0.0416 (11) | 0.0013 (7) | 0.0035 (7) | 0.0011 (7) |
C18 | 0.0418 (9) | 0.0437 (9) | 0.0426 (11) | 0.0019 (7) | 0.0014 (7) | −0.0006 (8) |
C19 | 0.0524 (11) | 0.0442 (10) | 0.0492 (12) | 0.0029 (8) | 0.0106 (9) | −0.0030 (8) |
C20 | 0.0458 (10) | 0.0487 (11) | 0.0679 (15) | 0.0062 (8) | 0.0143 (10) | −0.0026 (10) |
C21 | 0.0416 (10) | 0.0502 (11) | 0.0715 (16) | 0.0059 (8) | −0.0041 (9) | −0.0025 (10) |
C22 | 0.0486 (10) | 0.0396 (9) | 0.0505 (12) | 0.0040 (7) | −0.0051 (8) | 0.0009 (8) |
C23 | 0.0659 (14) | 0.0673 (14) | 0.0564 (15) | 0.0086 (11) | −0.0128 (11) | 0.0051 (11) |
C24 | 0.0789 (16) | 0.0806 (16) | 0.0496 (15) | 0.0104 (13) | 0.0172 (12) | −0.0021 (12) |
C25 | 0.0476 (10) | 0.0428 (9) | 0.0500 (12) | −0.0083 (8) | −0.0033 (8) | −0.0022 (8) |
C26 | 0.163 (3) | 0.0678 (16) | 0.0596 (19) | 0.0482 (19) | −0.0158 (19) | −0.0032 (13) |
C27 | 0.199 (4) | 0.085 (2) | 0.0463 (18) | 0.034 (2) | −0.015 (2) | −0.0003 (14) |
C28 | 0.0899 (19) | 0.0799 (17) | 0.0551 (17) | −0.0071 (14) | −0.0005 (13) | −0.0159 (13) |
C29 | 0.0768 (17) | 0.0828 (18) | 0.076 (2) | 0.0215 (14) | −0.0012 (14) | −0.0179 (15) |
C30 | 0.0710 (15) | 0.0653 (14) | 0.0610 (15) | 0.0153 (11) | −0.0029 (11) | 0.0055 (11) |
Geometric parameters (Å, º) top
S1—O1 | 1.414 (2) | C16—C17 | 1.522 (2) |
S1—O2 | 1.422 (2) | C16—H16A | 0.9700 |
S1—N1 | 1.682 (2) | C16—H16B | 0.9700 |
S1—C10 | 1.760 (2) | C17—C18 | 1.386 (3) |
S2—C3 | 1.759 (2) | C17—C22 | 1.403 (3) |
S2—C25 | 1.780 (2) | C18—C19 | 1.389 (3) |
N1—C5 | 1.417 (2) | C18—H18 | 0.9300 |
N1—C2 | 1.416 (2) | C19—C20 | 1.388 (3) |
C2—C3 | 1.361 (3) | C19—C24 | 1.499 (3) |
C2—C16 | 1.496 (3) | C20—C21 | 1.375 (3) |
C3—C4 | 1.440 (3) | C20—H20 | 0.9300 |
C4—C9 | 1.395 (3) | C21—C22 | 1.397 (3) |
C4—C5 | 1.396 (3) | C21—H21 | 0.9300 |
C5—C6 | 1.385 (3) | C22—C23 | 1.501 (3) |
C6—C7 | 1.381 (3) | C23—H23A | 0.9600 |
C6—H6 | 0.9300 | C23—H23B | 0.9600 |
C7—C8 | 1.380 (4) | C23—H23C | 0.9600 |
C7—H7 | 0.9300 | C24—H24A | 0.9600 |
C8—C9 | 1.375 (3) | C24—H24B | 0.9600 |
C8—H8 | 0.9300 | C24—H24C | 0.9600 |
C9—H9 | 0.9300 | C25—C26 | 1.366 (4) |
C10—C11 | 1.385 (3) | C25—C30 | 1.368 (3) |
C10—C15 | 1.386 (3) | C26—C27 | 1.374 (4) |
C11—C12 | 1.376 (3) | C26—H26 | 0.9300 |
C11—H11 | 0.9300 | C27—C28 | 1.331 (4) |
C12—C13 | 1.370 (3) | C27—H27 | 0.9300 |
C12—H12 | 0.9300 | C28—C29 | 1.356 (4) |
C13—C14 | 1.374 (3) | C28—H28 | 0.9300 |
C13—H13 | 0.9300 | C29—C30 | 1.382 (4) |
C14—C15 | 1.374 (3) | C29—H29 | 0.9300 |
C14—H14 | 0.9300 | C30—H30 | 0.9300 |
C15—H15 | 0.9300 | | |
| | | |
O1—S1—O2 | 120.6 (1) | C2—C16—H16A | 108.4 |
O1—S1—N1 | 106.7 (1) | C17—C16—H16A | 108.4 |
O2—S1—N1 | 105.5 (1) | C2—C16—H16B | 108.4 |
O1—S1—C10 | 109.2 (1) | C17—C16—H16B | 108.4 |
O2—S1—C10 | 108.7 (1) | H16A—C16—H16B | 107.5 |
N1—S1—C10 | 105.0 (1) | C18—C17—C22 | 119.56 (17) |
C3—S2—C25 | 103.0 (1) | C18—C17—C16 | 119.67 (17) |
C5—N1—C2 | 108.5 (2) | C22—C17—C16 | 120.74 (17) |
C5—N1—S1 | 122.1 (1) | C19—C18—C17 | 122.55 (19) |
C2—N1—S1 | 127.8 (1) | C19—C18—H18 | 118.7 |
C3—C2—N1 | 107.94 (16) | C17—C18—H18 | 118.7 |
C3—C2—C16 | 127.12 (17) | C20—C19—C18 | 117.4 (2) |
N1—C2—C16 | 124.72 (17) | C20—C19—C24 | 121.8 (2) |
C2—C3—C4 | 108.97 (16) | C18—C19—C24 | 120.7 (2) |
C2—C3—S2 | 125.48 (15) | C21—C20—C19 | 120.88 (19) |
C4—C3—S2 | 125.25 (15) | C21—C20—H20 | 119.6 |
C9—C4—C5 | 119.64 (19) | C19—C20—H20 | 119.6 |
C9—C4—C3 | 133.04 (19) | C20—C21—C22 | 121.9 (2) |
C5—C4—C3 | 107.32 (17) | C20—C21—H21 | 119.1 |
C6—C5—C4 | 121.74 (19) | C22—C21—H21 | 119.1 |
C6—C5—N1 | 130.98 (18) | C21—C22—C17 | 117.60 (19) |
C4—C5—N1 | 107.27 (16) | C21—C22—C23 | 119.95 (19) |
C7—C6—C5 | 117.4 (2) | C17—C22—C23 | 122.45 (19) |
C7—C6—H6 | 121.3 | C22—C23—H23A | 109.5 |
C5—C6—H6 | 121.3 | C22—C23—H23B | 109.5 |
C6—C7—C8 | 121.4 (2) | H23A—C23—H23B | 109.5 |
C6—C7—H7 | 119.3 | C22—C23—H23C | 109.5 |
C8—C7—H7 | 119.3 | H23A—C23—H23C | 109.5 |
C9—C8—C7 | 121.3 (2) | H23B—C23—H23C | 109.5 |
C9—C8—H8 | 119.3 | C19—C24—H24A | 109.5 |
C7—C8—H8 | 119.3 | C19—C24—H24B | 109.5 |
C8—C9—C4 | 118.4 (2) | H24A—C24—H24B | 109.5 |
C8—C9—H9 | 120.8 | C19—C24—H24C | 109.5 |
C4—C9—H9 | 120.8 | H24A—C24—H24C | 109.5 |
C11—C10—C15 | 120.73 (19) | H24B—C24—H24C | 109.5 |
C11—C10—S1 | 120.57 (15) | C26—C25—C30 | 118.4 (2) |
C15—C10—S1 | 118.69 (16) | C26—C25—S2 | 122.12 (18) |
C12—C11—C10 | 119.01 (19) | C30—C25—S2 | 119.33 (17) |
C12—C11—H11 | 120.5 | C25—C26—C27 | 120.0 (3) |
C10—C11—H11 | 120.5 | C25—C26—H26 | 120.0 |
C13—C12—C11 | 120.4 (2) | C27—C26—H26 | 120.0 |
C13—C12—H12 | 119.8 | C28—C27—C26 | 121.6 (3) |
C11—C12—H12 | 119.8 | C28—C27—H27 | 119.2 |
C12—C13—C14 | 120.5 (2) | C26—C27—H27 | 119.2 |
C12—C13—H13 | 119.7 | C27—C28—C29 | 119.4 (3) |
C14—C13—H13 | 119.7 | C27—C28—H28 | 120.3 |
C15—C14—C13 | 120.2 (2) | C29—C28—H28 | 120.3 |
C15—C14—H14 | 119.9 | C28—C29—C30 | 120.1 (3) |
C13—C14—H14 | 119.9 | C28—C29—H29 | 119.9 |
C14—C15—C10 | 119.1 (2) | C30—C29—H29 | 119.9 |
C14—C15—H15 | 120.4 | C25—C30—C29 | 120.4 (2) |
C10—C15—H15 | 120.4 | C25—C30—H30 | 119.8 |
C2—C16—C17 | 115.5 (2) | C29—C30—H30 | 119.8 |
| | | |
O1—S1—N1—C5 | 168.30 (14) | O1—S1—C10—C15 | 16.28 (18) |
O2—S1—N1—C5 | 38.89 (17) | O2—S1—C10—C15 | 149.7 (2) |
C10—S1—N1—C5 | −75.92 (16) | N1—S1—C10—C15 | −97.77 (16) |
O1—S1—N1—C2 | −27.64 (18) | C15—C10—C11—C12 | 2.1 (3) |
O2—S1—N1—C2 | −157.06 (16) | S1—C10—C11—C12 | −179.03 (17) |
C10—S1—N1—C2 | 88.13 (17) | C10—C11—C12—C13 | −2.0 (4) |
C5—N1—C2—C3 | −1.0 (2) | C11—C12—C13—C14 | 1.3 (4) |
S1—N1—C2—C3 | −166.77 (14) | C12—C13—C14—C15 | −0.7 (4) |
C5—N1—C2—C16 | −175.99 (16) | C13—C14—C15—C10 | 0.8 (3) |
S1—N1—C2—C16 | 18.2 (3) | C11—C10—C15—C14 | −1.5 (3) |
N1—C2—C3—C4 | 0.8 (2) | S1—C10—C15—C14 | 179.59 (16) |
C16—C2—C3—C4 | 175.67 (17) | C3—C2—C16—C17 | 103.6 (2) |
N1—C2—C3—S2 | −173.25 (13) | N1—C2—C16—C17 | −82.3 (2) |
C16—C2—C3—S2 | 1.6 (3) | C2—C16—C17—C18 | −35.8 (2) |
C25—S2—C3—C2 | −95.56 (18) | C2—C16—C17—C22 | 146.17 (18) |
C25—S2—C3—C4 | 91.33 (18) | C22—C17—C18—C19 | −1.3 (3) |
C2—C3—C4—C9 | 179.8 (2) | C16—C17—C18—C19 | −179.39 (17) |
S2—C3—C4—C9 | −6.1 (3) | C17—C18—C19—C20 | −1.0 (3) |
C2—C3—C4—C5 | −0.3 (2) | C17—C18—C19—C24 | 179.6 (2) |
S2—C3—C4—C5 | 173.73 (14) | C18—C19—C20—C21 | 2.3 (3) |
C9—C4—C5—C6 | 0.8 (3) | C24—C19—C20—C21 | −178.3 (2) |
C3—C4—C5—C6 | −179.04 (18) | C19—C20—C21—C22 | −1.2 (3) |
C9—C4—C5—N1 | 179.59 (18) | C20—C21—C22—C17 | −1.1 (3) |
C3—C4—C5—N1 | −0.3 (2) | C20—C21—C22—C23 | 178.8 (2) |
C2—N1—C5—C6 | 179.4 (2) | C18—C17—C22—C21 | 2.4 (3) |
S1—N1—C5—C6 | −13.8 (3) | C16—C17—C22—C21 | −179.62 (17) |
C2—N1—C5—C4 | 0.7 (2) | C18—C17—C22—C23 | −177.53 (19) |
S1—N1—C5—C4 | 167.52 (13) | C16—C17—C22—C23 | 0.5 (3) |
C4—C5—C6—C7 | −1.2 (3) | C3—S2—C25—C26 | −59.7 (3) |
N1—C5—C6—C7 | −179.7 (2) | C3—S2—C25—C30 | 124.04 (19) |
C5—C6—C7—C8 | 0.6 (4) | C30—C25—C26—C27 | −1.2 (5) |
C6—C7—C8—C9 | 0.4 (4) | S2—C25—C26—C27 | −177.4 (3) |
C7—C8—C9—C4 | −0.9 (4) | C25—C26—C27—C28 | −0.1 (6) |
C5—C4—C9—C8 | 0.3 (3) | C26—C27—C28—C29 | 1.3 (6) |
C3—C4—C9—C8 | −179.9 (2) | C27—C28—C29—C30 | −1.3 (5) |
O1—S1—C10—C11 | −162.65 (16) | C26—C25—C30—C29 | 1.2 (4) |
O2—S1—C10—C11 | −29.25 (19) | S2—C25—C30—C29 | 177.5 (2) |
N1—S1—C10—C11 | 83.30 (17) | C28—C29—C30—C25 | 0.1 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O2 | 0.93 | 2.31 | 2.900 (3) | 121 |
C15—H15···O1 | 0.93 | 2.55 | 2.914 (3) | 104 |
C16—H16A···S2 | 0.97 | 2.83 | 3.294 (2) | 110 |
C16—H16B···O1 | 0.97 | 2.38 | 2.881 (3) | 112 |