In the title compound, C
30H
24ClNO
3S, the phenylsulfonyl, chlorophenyl and methoxyphenyl rings are each almost perpendicular to the indole ring system. The crystal packing shows centrosymmetrically related pairs of molecules. Intermolecular C—H
O interactions are present.
Supporting information
CCDC reference: 277200
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.006 Å
- R factor = 0.085
- wR factor = 0.277
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.94
PLAT230_ALERT_2_B Hirshfeld Test Diff for C17 - C25 .. 10.70 su
PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for O3
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C28
Alert level C
RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25
Weighted R factor given 0.277
PLAT084_ALERT_2_C High R2 Value .................................. 0.28
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.76 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for O3 - C28 .. 6.15 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C14
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 C10
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C22
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C17 - C25 ... 1.54 Ang.
0 ALERT level A = In general: serious problem
4 ALERT level B = Potentially serious problem
12 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
13 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 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).
3-[
α-(4-Methoxyphenyl)-
β-(4-chlorophenyl)vinyl]-2-methyl-1-phenylsulfonyl-
1
H-indole
top
Crystal data top
C30H24ClNO3S | F(000) = 1072 |
Mr = 514.01 | Dx = 1.323 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5225 reflections |
a = 13.6402 (9) Å | θ = 2.3–25.6° |
b = 10.4097 (6) Å | µ = 0.26 mm−1 |
c = 18.4430 (11) Å | T = 273 K |
β = 99.756 (1)° | Block, colourless |
V = 2580.9 (3) Å3 | 0.24 × 0.22 × 0.19 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 4054 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.022 |
Graphite monochromator | θmax = 28.0°, θmin = 2.3° |
ω scans | h = −17→14 |
15377 measured reflections | k = −13→13 |
5533 independent reflections | l = −23→24 |
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)] = 0.085 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.277 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.1623P)2 + 1.4648P] where P = (Fo2 + 2Fc2)/3 |
5533 reflections | (Δ/σ)max < 0.001 |
327 parameters | Δρmax = 0.98 e Å−3 |
0 restraints | Δρmin = −0.51 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 | 0.30984 (7) | 0.85500 (7) | 0.20721 (6) | 0.0676 (4) | |
Cl1 | 0.07037 (12) | 0.34662 (15) | −0.10709 (8) | 0.1114 (5) | |
O1 | 0.4143 (2) | 0.8614 (3) | 0.2226 (2) | 0.1022 (12) | |
O2 | 0.2522 (3) | 0.9572 (2) | 0.22978 (18) | 0.0935 (10) | |
O3 | 0.4508 (4) | 0.1867 (5) | 0.5500 (3) | 0.1487 (18) | |
N1 | 0.2763 (2) | 0.7239 (2) | 0.24790 (15) | 0.0560 (7) | |
C2 | 0.3202 (2) | 0.6006 (3) | 0.24180 (19) | 0.0540 (7) | |
C3 | 0.2578 (2) | 0.5116 (2) | 0.26004 (17) | 0.0480 (7) | |
C4 | 0.1706 (2) | 0.5734 (3) | 0.27728 (16) | 0.0475 (7) | |
C5 | 0.1810 (2) | 0.7052 (3) | 0.26764 (16) | 0.0493 (7) | |
C6 | 0.1076 (3) | 0.7913 (3) | 0.2801 (2) | 0.0709 (10) | |
H6 | 0.1149 | 0.8793 | 0.2741 | 0.085* | |
C7 | 0.0246 (4) | 0.7412 (5) | 0.3015 (3) | 0.0906 (14) | |
H7 | −0.0261 | 0.7966 | 0.3093 | 0.109* | |
C8 | 0.0132 (3) | 0.6107 (5) | 0.3118 (3) | 0.0858 (12) | |
H8 | −0.0445 | 0.5804 | 0.3264 | 0.103* | |
C9 | 0.0858 (3) | 0.5258 (4) | 0.3008 (2) | 0.0654 (9) | |
H9 | 0.0787 | 0.4383 | 0.3089 | 0.079* | |
C10 | 0.2716 (3) | 0.8276 (3) | 0.1138 (2) | 0.0616 (9) | |
C11 | 0.1715 (3) | 0.8342 (4) | 0.0859 (2) | 0.0764 (11) | |
H11 | 0.1258 | 0.8539 | 0.1164 | 0.092* | |
C12 | 0.1400 (5) | 0.8108 (6) | 0.0114 (3) | 0.1041 (17) | |
H12 | 0.0730 | 0.8151 | −0.0091 | 0.125* | |
C13 | 0.2102 (7) | 0.7813 (7) | −0.0312 (3) | 0.127 (2) | |
H13 | 0.1894 | 0.7669 | −0.0812 | 0.152* | |
C14 | 0.3069 (6) | 0.7723 (8) | −0.0038 (4) | 0.131 (2) | |
H14 | 0.3518 | 0.7492 | −0.0343 | 0.158* | |
C15 | 0.3404 (4) | 0.7969 (5) | 0.0693 (3) | 0.1006 (16) | |
H15 | 0.4079 | 0.7931 | 0.0886 | 0.121* | |
C16 | 0.4185 (3) | 0.5790 (4) | 0.2193 (3) | 0.0945 (15) | |
H16A | 0.4374 | 0.4907 | 0.2274 | 0.142* | |
H16B | 0.4674 | 0.6332 | 0.2479 | 0.142* | |
H16C | 0.4141 | 0.5992 | 0.1681 | 0.142* | |
C17 | 0.2766 (3) | 0.3709 (3) | 0.2665 (2) | 0.0644 (9) | |
C18 | 0.2556 (3) | 0.2917 (3) | 0.2105 (2) | 0.0675 (9) | |
H18 | 0.2724 | 0.2063 | 0.2208 | 0.081* | |
C19 | 0.2103 (3) | 0.3176 (3) | 0.1353 (2) | 0.0589 (8) | |
C20 | 0.1742 (3) | 0.4323 (3) | 0.1024 (2) | 0.0705 (10) | |
H20 | 0.1786 | 0.5070 | 0.1304 | 0.085* | |
C21 | 0.1326 (3) | 0.4376 (4) | 0.0302 (2) | 0.0792 (11) | |
H21 | 0.1087 | 0.5155 | 0.0097 | 0.095* | |
C22 | 0.1253 (3) | 0.3287 (4) | −0.0134 (2) | 0.0720 (10) | |
C23 | 0.1577 (3) | 0.2153 (4) | 0.0159 (3) | 0.0861 (13) | |
H23 | 0.1519 | 0.1414 | −0.0128 | 0.103* | |
C24 | 0.1993 (3) | 0.2101 (3) | 0.0885 (3) | 0.0783 (11) | |
H24 | 0.2217 | 0.1310 | 0.1081 | 0.094* | |
C25 | 0.3242 (3) | 0.3208 (3) | 0.3432 (2) | 0.0628 (8) | |
C26 | 0.3401 (5) | 0.1957 (5) | 0.3608 (3) | 0.1055 (17) | |
H26 | 0.3213 | 0.1341 | 0.3246 | 0.127* | |
C27 | 0.3827 (5) | 0.1556 (5) | 0.4300 (4) | 0.1158 (19) | |
H27 | 0.3933 | 0.0683 | 0.4389 | 0.139* | |
C28 | 0.4099 (3) | 0.2420 (5) | 0.4864 (3) | 0.0836 (12) | |
C29 | 0.3942 (4) | 0.3686 (4) | 0.4700 (2) | 0.0811 (11) | |
H29 | 0.4125 | 0.4303 | 0.5062 | 0.097* | |
C30 | 0.3516 (3) | 0.4060 (4) | 0.4003 (2) | 0.0727 (10) | |
H30 | 0.3406 | 0.4931 | 0.3911 | 0.087* | |
C31 | 0.4708 (4) | 0.2690 (6) | 0.6074 (3) | 0.119 (2) | |
H31A | 0.5196 | 0.3304 | 0.5979 | 0.179* | |
H31B | 0.4962 | 0.2219 | 0.6513 | 0.179* | |
H31C | 0.4110 | 0.3130 | 0.6137 | 0.179* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0798 (6) | 0.0351 (4) | 0.0797 (7) | −0.0141 (3) | −0.0093 (5) | 0.0098 (3) |
Cl1 | 0.1192 (11) | 0.1329 (12) | 0.0748 (8) | 0.0042 (8) | −0.0046 (8) | −0.0144 (7) |
O1 | 0.086 (2) | 0.0754 (18) | 0.130 (3) | −0.0372 (15) | −0.0237 (19) | 0.0312 (17) |
O2 | 0.144 (3) | 0.0327 (11) | 0.098 (2) | −0.0005 (13) | 0.0032 (19) | −0.0024 (12) |
O3 | 0.130 (4) | 0.179 (5) | 0.129 (4) | 0.005 (3) | −0.003 (3) | 0.066 (4) |
N1 | 0.0671 (16) | 0.0333 (11) | 0.0642 (17) | −0.0003 (10) | 0.0018 (14) | 0.0066 (10) |
C2 | 0.0523 (16) | 0.0393 (13) | 0.068 (2) | 0.0066 (11) | 0.0029 (15) | 0.0102 (13) |
C3 | 0.0518 (15) | 0.0341 (12) | 0.0557 (18) | 0.0028 (10) | 0.0022 (13) | 0.0003 (11) |
C4 | 0.0530 (16) | 0.0430 (14) | 0.0439 (16) | 0.0015 (11) | 0.0008 (13) | −0.0063 (11) |
C5 | 0.0645 (18) | 0.0418 (13) | 0.0388 (15) | 0.0076 (12) | 0.0004 (14) | −0.0020 (11) |
C6 | 0.095 (3) | 0.0513 (17) | 0.066 (2) | 0.0241 (17) | 0.013 (2) | −0.0002 (15) |
C7 | 0.091 (3) | 0.092 (3) | 0.095 (3) | 0.037 (2) | 0.032 (3) | −0.002 (2) |
C8 | 0.070 (2) | 0.092 (3) | 0.100 (3) | 0.008 (2) | 0.030 (2) | −0.007 (2) |
C9 | 0.0611 (19) | 0.0621 (19) | 0.073 (2) | −0.0036 (15) | 0.0114 (18) | −0.0065 (16) |
C10 | 0.068 (2) | 0.0476 (16) | 0.068 (2) | −0.0071 (14) | 0.0078 (18) | 0.0183 (14) |
C11 | 0.074 (2) | 0.080 (3) | 0.072 (3) | −0.0058 (19) | 0.003 (2) | 0.0129 (19) |
C12 | 0.112 (4) | 0.118 (4) | 0.073 (3) | −0.028 (3) | −0.011 (3) | 0.023 (3) |
C13 | 0.183 (7) | 0.138 (5) | 0.057 (3) | −0.029 (5) | 0.017 (4) | 0.015 (3) |
C14 | 0.156 (6) | 0.164 (6) | 0.084 (4) | 0.007 (5) | 0.049 (4) | 0.030 (4) |
C15 | 0.093 (3) | 0.114 (4) | 0.101 (4) | 0.005 (3) | 0.036 (3) | 0.038 (3) |
C16 | 0.066 (2) | 0.070 (2) | 0.153 (5) | 0.0094 (19) | 0.032 (3) | 0.037 (3) |
C17 | 0.062 (2) | 0.0353 (13) | 0.101 (3) | 0.0027 (12) | 0.0283 (19) | 0.0025 (15) |
C18 | 0.086 (3) | 0.0442 (16) | 0.073 (2) | 0.0071 (15) | 0.016 (2) | 0.0045 (15) |
C19 | 0.0586 (18) | 0.0535 (16) | 0.065 (2) | 0.0034 (14) | 0.0115 (16) | 0.0098 (14) |
C20 | 0.099 (3) | 0.0426 (16) | 0.061 (2) | 0.0061 (16) | −0.011 (2) | −0.0027 (14) |
C21 | 0.099 (3) | 0.0554 (19) | 0.075 (3) | −0.0005 (19) | −0.009 (2) | 0.0067 (17) |
C22 | 0.067 (2) | 0.085 (3) | 0.063 (2) | −0.0045 (18) | 0.0097 (19) | −0.0119 (18) |
C23 | 0.091 (3) | 0.073 (3) | 0.093 (3) | 0.000 (2) | 0.012 (3) | −0.028 (2) |
C24 | 0.089 (3) | 0.0440 (17) | 0.104 (3) | 0.0095 (16) | 0.021 (2) | 0.0060 (18) |
C25 | 0.0581 (19) | 0.0638 (19) | 0.066 (2) | −0.0035 (15) | 0.0088 (17) | 0.0032 (16) |
C26 | 0.148 (5) | 0.067 (3) | 0.091 (3) | −0.004 (3) | −0.010 (3) | −0.001 (2) |
C27 | 0.150 (5) | 0.064 (3) | 0.123 (5) | 0.002 (3) | −0.007 (4) | 0.022 (3) |
C28 | 0.073 (2) | 0.098 (3) | 0.075 (3) | 0.002 (2) | 0.000 (2) | 0.035 (2) |
C29 | 0.089 (3) | 0.087 (3) | 0.063 (3) | −0.004 (2) | −0.002 (2) | 0.003 (2) |
C30 | 0.090 (3) | 0.064 (2) | 0.061 (2) | 0.0024 (19) | 0.000 (2) | 0.0048 (17) |
C31 | 0.078 (3) | 0.169 (6) | 0.101 (4) | −0.017 (3) | −0.010 (3) | 0.066 (4) |
Geometric parameters (Å, º) top
S1—O1 | 1.407 (3) | C14—H14 | 0.9300 |
S1—O2 | 1.426 (3) | C15—H15 | 0.9300 |
S1—N1 | 1.658 (2) | C16—H16A | 0.9600 |
S1—C10 | 1.738 (4) | C16—H16B | 0.9600 |
Cl1—C22 | 1.773 (4) | C16—H16C | 0.9600 |
O3—C28 | 1.340 (6) | C17—C18 | 1.314 (5) |
O3—C31 | 1.353 (4) | C17—C25 | 1.544 (6) |
N1—C5 | 1.421 (4) | C18—C19 | 1.444 (5) |
N1—C2 | 1.429 (4) | C18—H18 | 0.9300 |
C2—C3 | 1.339 (4) | C19—C20 | 1.392 (5) |
C2—C16 | 1.485 (5) | C19—C24 | 1.406 (5) |
C3—C4 | 1.434 (4) | C20—C21 | 1.357 (6) |
C3—C17 | 1.488 (4) | C20—H20 | 0.9300 |
C4—C5 | 1.394 (4) | C21—C22 | 1.382 (6) |
C4—C9 | 1.394 (5) | C21—H21 | 0.9300 |
C5—C6 | 1.391 (4) | C22—C23 | 1.342 (6) |
C6—C7 | 1.365 (6) | C23—C24 | 1.364 (6) |
C6—H6 | 0.9300 | C23—H23 | 0.9300 |
C7—C8 | 1.384 (7) | C24—H24 | 0.9300 |
C7—H7 | 0.9300 | C25—C26 | 1.351 (6) |
C8—C9 | 1.368 (5) | C25—C30 | 1.379 (5) |
C8—H8 | 0.9300 | C26—C27 | 1.374 (8) |
C9—H9 | 0.9300 | C26—H26 | 0.9300 |
C10—C11 | 1.376 (5) | C27—C28 | 1.378 (8) |
C10—C15 | 1.384 (6) | C27—H27 | 0.9300 |
C11—C12 | 1.391 (7) | C28—C29 | 1.362 (6) |
C11—H11 | 0.9300 | C29—C30 | 1.374 (6) |
C12—C13 | 1.371 (9) | C29—H29 | 0.9300 |
C12—H12 | 0.9300 | C30—H30 | 0.9300 |
C13—C14 | 1.334 (9) | C31—H31A | 0.9600 |
C13—H13 | 0.9300 | C31—H31B | 0.9600 |
C14—C15 | 1.373 (9) | C31—H31C | 0.9600 |
| | | |
O1—S1—O2 | 119.7 (2) | C2—C16—H16B | 109.5 |
O1—S1—N1 | 107.2 (2) | H16A—C16—H16B | 109.5 |
O2—S1—N1 | 105.9 (2) | C2—C16—H16C | 109.5 |
O1—S1—C10 | 109.4 (2) | H16A—C16—H16C | 109.5 |
O2—S1—C10 | 108.9 (2) | H16B—C16—H16C | 109.5 |
N1—S1—C10 | 104.8 (1) | C18—C17—C3 | 122.9 (4) |
C28—O3—C31 | 114.3 (5) | C18—C17—C25 | 120.7 (3) |
C5—N1—C2 | 108.1 (2) | C3—C17—C25 | 116.4 (3) |
C5—N1—S1 | 124.3 (2) | C17—C18—C19 | 129.6 (3) |
C2—N1—S1 | 123.5 (2) | C17—C18—H18 | 115.2 |
C3—C2—N1 | 108.0 (3) | C19—C18—H18 | 115.2 |
C3—C2—C16 | 127.4 (3) | C20—C19—C24 | 114.9 (3) |
N1—C2—C16 | 124.6 (3) | C20—C19—C18 | 129.9 (3) |
C2—C3—C4 | 109.4 (2) | C24—C19—C18 | 115.2 (3) |
C2—C3—C17 | 126.4 (3) | C21—C20—C19 | 121.5 (3) |
C4—C3—C17 | 124.2 (3) | C21—C20—H20 | 119.3 |
C5—C4—C9 | 119.8 (3) | C19—C20—H20 | 119.3 |
C5—C4—C3 | 107.9 (3) | C20—C21—C22 | 120.9 (4) |
C9—C4—C3 | 132.3 (3) | C20—C21—H21 | 119.6 |
C4—C5—C6 | 121.4 (3) | C22—C21—H21 | 119.6 |
C4—C5—N1 | 106.6 (2) | C23—C22—C21 | 120.1 (4) |
C6—C5—N1 | 131.9 (3) | C23—C22—Cl1 | 122.7 (3) |
C7—C6—C5 | 117.2 (3) | C21—C22—Cl1 | 117.2 (3) |
C7—C6—H6 | 121.4 | C22—C23—C24 | 119.0 (4) |
C5—C6—H6 | 121.4 | C22—C23—H23 | 120.5 |
C6—C7—C8 | 122.2 (4) | C24—C23—H23 | 120.5 |
C6—C7—H7 | 118.9 | C23—C24—C19 | 123.7 (3) |
C8—C7—H7 | 118.9 | C23—C24—H24 | 118.1 |
C9—C8—C7 | 120.9 (4) | C19—C24—H24 | 118.1 |
C9—C8—H8 | 119.5 | C26—C25—C30 | 115.1 (4) |
C7—C8—H8 | 119.5 | C26—C25—C17 | 124.9 (4) |
C8—C9—C4 | 118.4 (4) | C30—C25—C17 | 120.0 (3) |
C8—C9—H9 | 120.8 | C25—C26—C27 | 122.9 (5) |
C4—C9—H9 | 120.8 | C25—C26—H26 | 118.6 |
C11—C10—C15 | 121.4 (4) | C27—C26—H26 | 118.6 |
C11—C10—S1 | 118.3 (3) | C26—C27—C28 | 121.3 (4) |
C15—C10—S1 | 120.3 (4) | C26—C27—H27 | 119.3 |
C12—C11—C10 | 118.7 (5) | C28—C27—H27 | 119.3 |
C12—C11—H11 | 120.7 | O3—C28—C29 | 129.6 (5) |
C10—C11—H11 | 120.7 | O3—C28—C27 | 113.5 (5) |
C13—C12—C11 | 118.5 (5) | C29—C28—C27 | 116.9 (4) |
C13—C12—H12 | 120.8 | C28—C29—C30 | 120.5 (4) |
C11—C12—H12 | 120.8 | C28—C29—H29 | 119.7 |
C14—C13—C12 | 122.7 (6) | C30—C29—H29 | 119.7 |
C14—C13—H13 | 118.6 | C25—C30—C29 | 123.3 (4) |
C12—C13—H13 | 118.6 | C25—C30—H30 | 118.3 |
C13—C14—C15 | 120.1 (6) | C29—C30—H30 | 118.3 |
C13—C14—H14 | 120.0 | O3—C31—H31A | 109.5 |
C15—C14—H14 | 120.0 | O3—C31—H31B | 109.5 |
C10—C15—C14 | 118.6 (5) | H31A—C31—H31B | 109.5 |
C10—C15—H15 | 120.7 | O3—C31—H31C | 109.5 |
C14—C15—H15 | 120.7 | H31A—C31—H31C | 109.5 |
C2—C16—H16A | 109.5 | H31B—C31—H31C | 109.5 |
| | | |
O1—S1—N1—C5 | 157.2 (3) | C10—C11—C12—C13 | 0.5 (7) |
O2—S1—N1—C5 | 28.3 (3) | C11—C12—C13—C14 | 1.0 (10) |
C10—S1—N1—C5 | −86.7 (3) | C12—C13—C14—C15 | −2.1 (11) |
O1—S1—N1—C2 | −48.4 (3) | C11—C10—C15—C14 | −0.3 (7) |
O2—S1—N1—C2 | −177.3 (3) | S1—C10—C15—C14 | 178.1 (4) |
C10—S1—N1—C2 | 67.7 (3) | C13—C14—C15—C10 | 1.7 (10) |
C5—N1—C2—C3 | −2.7 (4) | C2—C3—C17—C18 | −88.1 (5) |
S1—N1—C2—C3 | −160.6 (2) | C4—C3—C17—C18 | 96.0 (4) |
C5—N1—C2—C16 | 177.6 (4) | C2—C3—C17—C25 | 91.0 (4) |
S1—N1—C2—C16 | 19.7 (5) | C4—C3—C17—C25 | −84.9 (4) |
N1—C2—C3—C4 | 1.0 (4) | C3—C17—C18—C19 | −1.8 (6) |
C16—C2—C3—C4 | −179.2 (4) | C25—C17—C18—C19 | 179.1 (3) |
N1—C2—C3—C17 | −175.4 (3) | C17—C18—C19—C20 | −2.0 (7) |
C16—C2—C3—C17 | 4.3 (6) | C17—C18—C19—C24 | 179.3 (4) |
C2—C3—C4—C5 | 1.0 (4) | C24—C19—C20—C21 | −0.6 (6) |
C17—C3—C4—C5 | 177.6 (3) | C18—C19—C20—C21 | −179.3 (4) |
C2—C3—C4—C9 | −178.2 (3) | C19—C20—C21—C22 | −0.4 (7) |
C17—C3—C4—C9 | −1.6 (6) | C20—C21—C22—C23 | 1.3 (7) |
C9—C4—C5—C6 | −0.9 (5) | C20—C21—C22—Cl1 | −179.6 (3) |
C3—C4—C5—C6 | 179.8 (3) | C21—C22—C23—C24 | −1.2 (7) |
C9—C4—C5—N1 | 176.7 (3) | Cl1—C22—C23—C24 | 179.8 (3) |
C3—C4—C5—N1 | −2.6 (3) | C22—C23—C24—C19 | 0.2 (7) |
C2—N1—C5—C4 | 3.3 (3) | C20—C19—C24—C23 | 0.7 (6) |
S1—N1—C5—C4 | 161.0 (2) | C18—C19—C24—C23 | 179.6 (4) |
C2—N1—C5—C6 | −179.6 (4) | C18—C17—C25—C26 | −5.9 (6) |
S1—N1—C5—C6 | −21.8 (5) | C3—C17—C25—C26 | 175.0 (4) |
C4—C5—C6—C7 | −0.6 (5) | C18—C17—C25—C30 | 175.9 (4) |
N1—C5—C6—C7 | −177.4 (4) | C3—C17—C25—C30 | −3.2 (5) |
C5—C6—C7—C8 | 1.1 (7) | C30—C25—C26—C27 | −1.6 (8) |
C6—C7—C8—C9 | 0.0 (8) | C17—C25—C26—C27 | −179.9 (5) |
C7—C8—C9—C4 | −1.5 (7) | C25—C26—C27—C28 | 1.5 (10) |
C5—C4—C9—C8 | 1.9 (5) | C31—O3—C28—C29 | 6.6 (8) |
C3—C4—C9—C8 | −179.0 (4) | C31—O3—C28—C27 | −175.1 (5) |
O1—S1—C10—C11 | −172.0 (3) | C26—C27—C28—O3 | −179.7 (6) |
O2—S1—C10—C11 | −39.5 (3) | C26—C27—C28—C29 | −1.1 (9) |
N1—S1—C10—C11 | 73.4 (3) | O3—C28—C29—C30 | 179.3 (5) |
O1—S1—C10—C15 | 9.6 (4) | C27—C28—C29—C30 | 1.0 (7) |
O2—S1—C10—C15 | 142.1 (3) | C26—C25—C30—C29 | 1.6 (6) |
N1—S1—C10—C15 | −105.0 (3) | C17—C25—C30—C29 | 179.9 (4) |
C15—C10—C11—C12 | −0.8 (6) | C28—C29—C30—C25 | −1.3 (7) |
S1—C10—C11—C12 | −179.2 (3) | | |
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 | 2.889 (5) | 120 |
C16—H16A···O1i | 0.96 | 2.47 | 3.264 (5) | 140 |
C31—H31B···O1ii | 0.96 | 2.59 | 3.531 (6) | 168 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1. |