3-[β-(4-Chloro­phen­yl)-α-(4-methoxy­phen­yl)vin­yl]-2-meth­yl-1-phenyl­sulfon­yl-1H-indole

In the title compound, C₃₀H₂₄ClNO₃S, 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.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](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

---

Computing details

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- 1H-indole

Crystal data

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) Å^3	0.24 × 0.22 × 0.19 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.085	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.277	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.1623P)^2 + 1.4648P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O1^i	0.96	2.47	3.264 (5)	140
C31—H31B···O1^ii	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.