Diethyl 2-[(2-benzyl-1-phenyl-sulfonyl-1H-indol-3-yl)methyl-ene]malonate.

In the title compound, C(29)H(27)NO(6)S, the sulfonyl-bound phenyl ring is almost perpendicular to the indole ring system [dihedral angle = 87.96 (6)°], while the benzyl-phenyl ring is oriented at an angle of 76.8 (7)°. An intra-molecular C-H⋯O hydrogen bond is observed. In the crystal structure, mol-ecules are linked into a zigzag C(10) chain along the b axis by inter-molecular C-H⋯O hydrogen bonds.

Related literature

For general background to indole derivatives and their biological activity, see: Andreani et al. (2001 ▶); Bassindale (1984 ▶); Quetin-Leclercq et al. (1995 ▶); Singh et al. (2000 ▶); Tsotinis et al. (1997 ▶); Wang & Ng (2002 ▶).

Experimental

Crystal data

C29H27NO6S

M = 517.58

Monoclinic,

a = 10.8280 (9) Å

b = 13.7762 (11) Å

c = 17.6832 (16) Å

β = 91.341 (4)°

V = 2637.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 293 (2) K

0.30 × 0.25 × 0.16 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.952, T max = 0.968

34168 measured reflections

7583 independent reflections

4683 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.142

S = 1.02

7583 reflections

334 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680804004X/ci2729sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680804004X/ci2729Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C29H27NO6S	F(000) = 1088
Mr = 517.58	Dx = 1.304 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7583 reflections
a = 10.8280 (9) Å	θ = 2.2–29.9°
b = 13.7762 (11) Å	µ = 0.17 mm−1
c = 17.6832 (16) Å	T = 293 K
β = 91.341 (4)°	Block, colourless
V = 2637.1 (4) Å3	0.30 × 0.25 × 0.16 mm
Z = 4

Bruker Kappa APEXII area-detector diffractometer	7583 independent reflections
Radiation source: fine-focus sealed tube	4683 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω and φ scans	θmax = 29.9°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −15→12
Tmin = 0.952, Tmax = 0.968	k = −14→19
34168 measured reflections	l = −22→24

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0628P)2 + 0.5537P] where P = (Fo2 + 2Fc2)/3
7583 reflections	(Δ/σ)max = 0.021
334 parameters	Δρmax = 0.25 e Å−3
1 restraint	Δρmin = −0.27 e Å−3

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.

	x	y	z	Uiso*/Ueq
C2	0.62844 (14)	0.59182 (11)	0.04158 (8)	0.0397 (3)
C3	0.51591 (14)	0.62397 (12)	0.06343 (8)	0.0413 (3)
C4	0.46420 (15)	0.55336 (12)	0.11419 (8)	0.0429 (3)
C5	0.54970 (15)	0.47797 (12)	0.12226 (8)	0.0433 (4)
C6	0.52568 (17)	0.39664 (14)	0.16628 (10)	0.0546 (4)
H6	0.5824	0.3462	0.1707	0.066*
C7	0.41513 (19)	0.39360 (15)	0.20291 (10)	0.0612 (5)
H7	0.3981	0.3409	0.2338	0.073*
C8	0.32872 (18)	0.46698 (15)	0.19496 (10)	0.0597 (5)
H8	0.2546	0.4624	0.2202	0.072*
C9	0.35069 (16)	0.54695 (13)	0.15017 (10)	0.0524 (4)
H9	0.2915	0.5954	0.1440	0.063*
C10	0.86326 (16)	0.49835 (14)	0.16366 (10)	0.0524 (4)
C11	0.96281 (18)	0.55897 (16)	0.15389 (12)	0.0648 (5)
H11	0.9927	0.5708	0.1059	0.078*
C12	1.0176 (2)	0.60210 (19)	0.21722 (15)	0.0835 (7)
H12	1.0852	0.6430	0.2118	0.100*
C13	0.9725 (2)	0.5846 (2)	0.28747 (16)	0.0986 (9)
H13	1.0073	0.6158	0.3294	0.118*
C14	0.8760 (3)	0.5212 (3)	0.29651 (13)	0.1091 (10)
H14	0.8478	0.5080	0.3447	0.131*
C15	0.8210 (2)	0.4773 (2)	0.23443 (12)	0.0856 (7)
H15	0.7560	0.4340	0.2403	0.103*
C16	0.71395 (15)	0.64140 (12)	−0.01088 (8)	0.0446 (4)
H16A	0.6652	0.6821	−0.0449	0.053*
H16B	0.7534	0.5923	−0.0414	0.053*
C17	0.81366 (14)	0.70333 (12)	0.02598 (9)	0.0426 (3)
C18	0.93068 (15)	0.70523 (13)	−0.00413 (10)	0.0510 (4)
H18	0.9470	0.6673	−0.0462	0.061*
C19	1.02346 (18)	0.76232 (15)	0.02708 (12)	0.0647 (5)
H19	1.1014	0.7624	0.0061	0.078*
C20	1.00051 (19)	0.81899 (17)	0.08912 (13)	0.0724 (6)
H20	1.0630	0.8570	0.1107	0.087*
C21	0.8847 (2)	0.81906 (17)	0.11901 (12)	0.0741 (6)
H21	0.8686	0.8581	0.1605	0.089*
C22	0.79141 (16)	0.76163 (14)	0.08807 (10)	0.0567 (5)
H22	0.7135	0.7622	0.1091	0.068*
C23	0.46256 (15)	0.71538 (13)	0.03676 (9)	0.0477 (4)
H23	0.4694	0.7277	−0.0147	0.057*
C24	0.40536 (15)	0.78361 (12)	0.07624 (9)	0.0476 (4)
C25	0.36165 (19)	0.87182 (15)	0.03489 (12)	0.0619 (5)
C26	0.2677 (3)	1.02592 (18)	0.04540 (15)	0.1004 (9)
H26A	0.3365	1.0636	0.0270	0.120*
H26B	0.2122	1.0115	0.0030	0.120*
C27	0.2032 (3)	1.0801 (2)	0.10279 (18)	0.1203 (12)
H27A	0.1723	1.1397	0.0814	0.180*
H27B	0.2591	1.0943	0.1442	0.180*
H27C	0.1355	1.0421	0.1206	0.180*
C28	0.38732 (16)	0.77720 (12)	0.15970 (10)	0.0502 (4)
C29	0.4911 (2)	0.74032 (19)	0.27630 (11)	0.0809 (7)
H29A	0.4125	0.7117	0.2892	0.097*
H29B	0.5012	0.8004	0.3043	0.097*
C30	0.5929 (3)	0.6728 (2)	0.29586 (14)	0.1064 (9)
H30A	0.5924	0.6590	0.3491	0.160*
H30B	0.6703	0.7020	0.2834	0.160*
H30C	0.5821	0.6136	0.2679	0.160*
N1	0.65221 (12)	0.50118 (10)	0.07694 (7)	0.0434 (3)
O1	0.76255 (13)	0.34702 (9)	0.10092 (8)	0.0690 (4)
O2	0.85555 (12)	0.46945 (10)	0.01832 (7)	0.0633 (4)
O3	0.3719 (2)	0.88321 (13)	−0.03157 (9)	0.1094 (7)
O4	0.31220 (15)	0.93642 (10)	0.08018 (8)	0.0764 (4)
O5	0.29041 (13)	0.78452 (13)	0.18992 (8)	0.0796 (4)
O6	0.49406 (12)	0.75941 (10)	0.19517 (6)	0.0585 (3)
S1	0.78964 (4)	0.44550 (3)	0.08437 (2)	0.04989 (13)

	U11	U22	U33	U12	U13	U23
C2	0.0459 (8)	0.0424 (8)	0.0309 (7)	0.0023 (7)	0.0020 (6)	−0.0038 (6)
C3	0.0452 (8)	0.0447 (8)	0.0340 (7)	0.0016 (7)	0.0032 (6)	−0.0048 (6)
C4	0.0464 (8)	0.0455 (9)	0.0370 (8)	−0.0037 (7)	0.0048 (6)	−0.0059 (7)
C5	0.0489 (9)	0.0456 (9)	0.0355 (7)	−0.0019 (7)	0.0027 (6)	−0.0039 (6)
C6	0.0612 (11)	0.0529 (10)	0.0498 (10)	−0.0033 (8)	0.0006 (8)	0.0058 (8)
C7	0.0703 (12)	0.0621 (12)	0.0514 (10)	−0.0159 (10)	0.0063 (9)	0.0086 (9)
C8	0.0590 (11)	0.0694 (13)	0.0512 (10)	−0.0182 (10)	0.0143 (8)	−0.0059 (9)
C9	0.0486 (9)	0.0565 (10)	0.0524 (10)	−0.0037 (8)	0.0107 (8)	−0.0101 (8)
C10	0.0457 (9)	0.0609 (11)	0.0506 (9)	0.0128 (8)	0.0012 (7)	0.0029 (8)
C11	0.0536 (11)	0.0751 (13)	0.0653 (12)	0.0044 (10)	−0.0044 (9)	0.0152 (10)
C12	0.0632 (13)	0.0920 (17)	0.0942 (18)	−0.0040 (12)	−0.0210 (13)	0.0058 (14)
C13	0.0718 (16)	0.141 (2)	0.0823 (18)	0.0089 (16)	−0.0203 (13)	−0.0306 (17)
C14	0.0797 (17)	0.195 (3)	0.0526 (13)	−0.012 (2)	0.0023 (12)	−0.0129 (17)
C15	0.0687 (13)	0.137 (2)	0.0510 (12)	−0.0199 (14)	0.0061 (10)	−0.0014 (13)
C16	0.0485 (9)	0.0516 (9)	0.0338 (7)	0.0050 (7)	0.0063 (6)	−0.0001 (7)
C17	0.0439 (8)	0.0426 (8)	0.0415 (8)	0.0067 (7)	0.0062 (6)	0.0043 (7)
C18	0.0505 (9)	0.0530 (10)	0.0499 (9)	0.0071 (8)	0.0113 (7)	0.0025 (8)
C19	0.0500 (10)	0.0672 (13)	0.0775 (13)	−0.0016 (9)	0.0109 (9)	0.0031 (11)
C20	0.0570 (11)	0.0733 (14)	0.0868 (15)	−0.0107 (10)	−0.0022 (10)	−0.0109 (12)
C21	0.0729 (13)	0.0775 (15)	0.0720 (13)	−0.0009 (11)	0.0059 (11)	−0.0294 (11)
C22	0.0480 (9)	0.0650 (12)	0.0575 (10)	0.0042 (8)	0.0101 (8)	−0.0138 (9)
C23	0.0488 (9)	0.0541 (10)	0.0405 (8)	0.0058 (8)	0.0053 (7)	0.0017 (7)
C24	0.0456 (8)	0.0496 (9)	0.0477 (9)	0.0084 (7)	0.0050 (7)	0.0033 (7)
C25	0.0677 (12)	0.0595 (11)	0.0588 (11)	0.0184 (10)	0.0064 (9)	0.0085 (9)
C26	0.132 (2)	0.0731 (16)	0.0966 (17)	0.0495 (15)	0.0213 (15)	0.0311 (13)
C27	0.153 (3)	0.0816 (18)	0.128 (2)	0.0647 (19)	0.038 (2)	0.0285 (16)
C28	0.0561 (10)	0.0433 (9)	0.0516 (9)	0.0084 (8)	0.0111 (8)	−0.0023 (7)
C29	0.1101 (18)	0.0912 (16)	0.0414 (10)	−0.0064 (14)	−0.0021 (11)	−0.0033 (10)
C30	0.152 (3)	0.098 (2)	0.0674 (15)	0.0107 (19)	−0.0347 (16)	0.0001 (14)
N1	0.0451 (7)	0.0462 (7)	0.0392 (7)	0.0041 (6)	0.0041 (5)	0.0004 (6)
O1	0.0787 (9)	0.0475 (7)	0.0809 (9)	0.0133 (7)	0.0053 (7)	0.0002 (7)
O2	0.0642 (8)	0.0748 (9)	0.0517 (7)	0.0226 (7)	0.0178 (6)	−0.0014 (6)
O3	0.1778 (19)	0.0924 (12)	0.0589 (10)	0.0551 (13)	0.0223 (11)	0.0235 (8)
O4	0.0987 (11)	0.0608 (9)	0.0703 (9)	0.0373 (8)	0.0117 (8)	0.0129 (7)
O5	0.0693 (9)	0.1000 (12)	0.0707 (9)	0.0266 (8)	0.0279 (7)	0.0055 (8)
O6	0.0627 (8)	0.0694 (8)	0.0434 (6)	−0.0004 (6)	0.0007 (6)	−0.0052 (6)
S1	0.0533 (3)	0.0490 (3)	0.0476 (2)	0.01314 (19)	0.00624 (18)	−0.00205 (18)

C2—C3	1.361 (2)	C18—H18	0.93
C2—N1	1.417 (2)	C19—C20	1.374 (3)
C2—C16	1.492 (2)	C19—H19	0.93
C3—C4	1.445 (2)	C20—C21	1.372 (3)
C3—C23	1.459 (2)	C20—H20	0.93
C4—C5	1.396 (2)	C21—C22	1.386 (3)
C4—C9	1.400 (2)	C21—H21	0.93
C5—C6	1.392 (2)	C22—H22	0.93
C5—N1	1.421 (2)	C23—C24	1.332 (2)
C6—C7	1.375 (3)	C23—H23	0.93
C6—H6	0.93	C24—C25	1.490 (2)
C7—C8	1.382 (3)	C24—C28	1.496 (2)
C7—H7	0.93	C25—O3	1.193 (2)
C8—C9	1.381 (3)	C25—O4	1.319 (2)
C8—H8	0.93	C26—C27	1.452 (4)
C9—H9	0.93	C26—O4	1.455 (2)
C10—C15	1.373 (3)	C26—H26A	0.97
C10—C11	1.378 (3)	C26—H26B	0.97
C10—S1	1.7548 (18)	C27—H27A	0.96
C11—C12	1.389 (3)	C27—H27B	0.96
C11—H11	0.93	C27—H27C	0.96
C12—C13	1.367 (4)	C28—O5	1.193 (2)
C12—H12	0.93	C28—O6	1.325 (2)
C13—C14	1.373 (4)	C29—O6	1.460 (2)
C13—H13	0.93	C29—C30	1.477 (4)
C14—C15	1.377 (3)	C29—H29A	0.97
C14—H14	0.93	C29—H29B	0.97
C15—H15	0.93	C30—H30A	0.96
C16—C17	1.512 (2)	C30—H30B	0.96
C16—H16A	0.97	C30—H30C	0.96
C16—H16B	0.97	N1—S1	1.6766 (13)
C17—C18	1.386 (2)	O1—S1	1.4199 (14)
C17—C22	1.386 (2)	O2—S1	1.4216 (13)
C18—C19	1.381 (3)
C3—C2—N1	108.43 (13)	C21—C20—C19	119.47 (19)
C3—C2—C16	126.91 (14)	C21—C20—H20	120.3
N1—C2—C16	124.67 (13)	C19—C20—H20	120.3
C2—C3—C4	108.64 (14)	C20—C21—C22	120.78 (19)
C2—C3—C23	122.64 (15)	C20—C21—H21	119.6
C4—C3—C23	128.71 (14)	C22—C21—H21	119.6
C5—C4—C9	119.58 (15)	C21—C22—C17	120.34 (16)
C5—C4—C3	107.37 (14)	C21—C22—H22	119.8
C9—C4—C3	132.97 (16)	C17—C22—H22	119.8
C6—C5—C4	121.58 (15)	C24—C23—C3	128.67 (15)
C6—C5—N1	130.93 (16)	C24—C23—H23	115.7
C4—C5—N1	107.45 (13)	C3—C23—H23	115.7
C7—C6—C5	117.64 (18)	C23—C24—C25	117.68 (16)
C7—C6—H6	121.2	C23—C24—C28	123.27 (15)
C5—C6—H6	121.2	C25—C24—C28	119.02 (15)
C6—C7—C8	121.64 (18)	O3—C25—O4	123.89 (18)
C6—C7—H7	119.2	O3—C25—C24	123.70 (18)
C8—C7—H7	119.2	O4—C25—C24	112.41 (16)
C9—C8—C7	121.09 (17)	C27—C26—O4	107.5 (2)
C9—C8—H8	119.5	C27—C26—H26A	110.2
C7—C8—H8	119.5	O4—C26—H26A	110.2
C8—C9—C4	118.42 (17)	C27—C26—H26B	110.2
C8—C9—H9	120.8	O4—C26—H26B	110.2
C4—C9—H9	120.8	H26A—C26—H26B	108.5
C15—C10—C11	121.37 (19)	C26—C27—H27A	109.5
C15—C10—S1	119.07 (16)	C26—C27—H27B	109.5
C11—C10—S1	119.56 (15)	H27A—C27—H27B	109.5
C10—C11—C12	118.6 (2)	C26—C27—H27C	109.5
C10—C11—H11	120.7	H27A—C27—H27C	109.5
C12—C11—H11	120.7	H27B—C27—H27C	109.5
C13—C12—C11	120.2 (2)	O5—C28—O6	124.78 (17)
C13—C12—H12	119.9	O5—C28—C24	124.99 (17)
C11—C12—H12	119.9	O6—C28—C24	110.20 (14)
C12—C13—C14	120.5 (2)	O6—C29—C30	108.07 (19)
C12—C13—H13	119.8	O6—C29—H29A	110.1
C14—C13—H13	119.8	C30—C29—H29A	110.1
C13—C14—C15	120.2 (2)	O6—C29—H29B	110.1
C13—C14—H14	119.9	C30—C29—H29B	110.1
C15—C14—H14	119.9	H29A—C29—H29B	108.4
C10—C15—C14	119.1 (2)	C29—C30—H30A	109.5
C10—C15—H15	120.4	C29—C30—H30B	109.5
C14—C15—H15	120.4	H30A—C30—H30B	109.5
C2—C16—C17	115.95 (12)	C29—C30—H30C	109.5
C2—C16—H16A	108.3	H30A—C30—H30C	109.5
C17—C16—H16A	108.3	H30B—C30—H30C	109.5
C2—C16—H16B	108.3	C2—N1—C5	108.11 (12)
C17—C16—H16B	108.3	C2—N1—S1	126.11 (11)
H16A—C16—H16B	107.4	C5—N1—S1	123.82 (11)
C18—C17—C22	118.08 (16)	C25—O4—C26	116.75 (17)
C18—C17—C16	119.68 (14)	C28—O6—C29	117.36 (16)
C22—C17—C16	122.21 (14)	O1—S1—O2	120.08 (9)
C19—C18—C17	121.36 (17)	O1—S1—N1	105.43 (8)
C19—C18—H18	119.3	O2—S1—N1	106.92 (7)
C17—C18—H18	119.3	O1—S1—C10	108.90 (9)
C20—C19—C18	119.95 (18)	O2—S1—C10	109.44 (9)
C20—C19—H19	120.0	N1—S1—C10	104.98 (7)
C18—C19—H19	120.0
N1—C2—C3—C4	0.01 (17)	C3—C2—N1—S1	−164.69 (11)
C16—C2—C3—C4	179.63 (14)	C16—C2—N1—S1	15.7 (2)
N1—C2—C3—C23	−179.53 (13)	C6—C5—N1—C2	177.89 (16)
C16—C2—C3—C23	0.1 (2)	C4—C5—N1—C2	0.36 (16)
C2—C3—C4—C5	0.22 (17)	C6—C5—N1—S1	−17.2 (2)
C23—C3—C4—C5	179.72 (15)	C4—C5—N1—S1	165.27 (11)
C2—C3—C4—C9	−176.51 (17)	O4—C25—O3—O3	0.0 (3)
C23—C3—C4—C9	3.0 (3)	C24—C25—O3—O3	0.0 (3)
C9—C4—C5—C6	−0.9 (2)	O3—C25—O4—C26	0.4 (4)
C3—C4—C5—C6	−178.16 (14)	O3—C25—O4—C26	0.4 (4)
C9—C4—C5—N1	176.89 (14)	C24—C25—O4—C26	179.4 (2)
C3—C4—C5—N1	−0.35 (17)	C27—C26—O4—C25	172.6 (2)
C4—C5—C6—C7	−1.1 (2)	O5—C28—O6—C29	4.8 (3)
N1—C5—C6—C7	−178.33 (16)	C24—C28—O6—C29	−173.44 (16)
C5—C6—C7—C8	1.8 (3)	C30—C29—O6—C28	148.87 (19)
C6—C7—C8—C9	−0.5 (3)	O1—O1—S1—O2	0.00 (10)
C7—C8—C9—C4	−1.5 (3)	O1—O1—S1—O2	0.00 (10)
C5—C4—C9—C8	2.2 (2)	O1—O1—S1—O2	0.00 (10)
C3—C4—C9—C8	178.61 (16)	O1—O1—S1—N1	0.00 (9)
C15—C10—C11—C12	−2.5 (3)	O1—O1—S1—C10	0.00 (10)
S1—C10—C11—C12	178.27 (16)	O2—O2—S1—O1	0.00 (6)
C10—C11—C12—C13	−0.3 (3)	O2—O2—S1—O1	0.00 (6)
C11—C12—C13—C14	2.7 (4)	O2—O2—S1—O1	0.00 (6)
C12—C13—C14—C15	−2.3 (5)	O2—O2—S1—O1	0.00 (6)
C11—C10—C15—C14	2.9 (4)	O2—O2—S1—O2	0.00 (4)
S1—C10—C15—C14	−177.9 (2)	O2—O2—S1—O2	0.00 (4)
C13—C14—C15—C10	−0.5 (5)	O2—O2—S1—N1	0.00 (2)
C3—C2—C16—C17	95.29 (18)	O2—O2—S1—N1	0.00 (2)
N1—C2—C16—C17	−85.15 (19)	O2—O2—S1—C10	0.00 (5)
C2—C16—C17—C22	−40.0 (2)	O2—O2—S1—C10	0.00 (5)
C2—C16—C17—C18	142.20 (15)	C2—N1—S1—O1	−161.77 (13)
C22—C17—C18—C19	0.9 (3)	C5—N1—S1—O1	36.07 (15)
C16—C17—C18—C19	178.73 (16)	C2—N1—S1—O1	−161.77 (13)
C17—C18—C19—C20	−0.2 (3)	C5—N1—S1—O1	36.07 (15)
C18—C19—C20—C21	−0.7 (3)	C2—N1—S1—O2	−32.90 (15)
C19—C20—C21—C22	1.0 (4)	C5—N1—S1—O2	164.94 (13)
C20—C21—C22—C17	−0.3 (3)	C2—N1—S1—O2	−32.90 (15)
C18—C17—C22—C21	−0.6 (3)	C5—N1—S1—O2	164.94 (13)
C16—C17—C22—C21	−178.43 (18)	C2—N1—S1—O2	−32.90 (15)
C2—C3—C23—C24	−135.86 (19)	C5—N1—S1—O2	164.94 (13)
C4—C3—C23—C24	44.7 (3)	C2—N1—S1—C10	83.29 (14)
C3—C23—C24—C25	178.68 (17)	C5—N1—S1—C10	−78.86 (14)
C3—C23—C24—C28	0.9 (3)	C15—C10—S1—O1	−41.3 (2)
C23—C24—C25—O3	2.2 (3)	C11—C10—S1—O1	137.98 (16)
C28—C24—C25—O3	−179.9 (2)	C15—C10—S1—O1	−41.3 (2)
C23—C24—C25—O3	2.2 (3)	C11—C10—S1—O1	137.98 (16)
C28—C24—C25—O3	−179.9 (2)	C15—C10—S1—O2	−174.34 (17)
C23—C24—C25—O4	−176.75 (17)	C11—C10—S1—O2	4.93 (18)
C28—C24—C25—O4	1.1 (3)	C15—C10—S1—O2	−174.34 (17)
C23—C24—C28—O5	−126.2 (2)	C11—C10—S1—O2	4.93 (18)
C25—C24—C28—O5	56.1 (3)	C15—C10—S1—O2	−174.34 (17)
C23—C24—C28—O6	52.0 (2)	C11—C10—S1—O2	4.93 (18)
C25—C24—C28—O6	−125.73 (17)	C15—C10—S1—N1	71.20 (19)
C3—C2—N1—C5	−0.23 (16)	C11—C10—S1—N1	−109.53 (15)
C16—C2—N1—C5	−179.86 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.93	2.33	2.919 (2)	121
C7—H7···O5i	0.93	2.59	3.317 (2)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1	0.93	2.33	2.919 (2)	121
C7—H7⋯O5i	0.93	2.59	3.317 (2)	135

Symmetry code: (i) .