Diethyl 2-{[3-(2,4,6-trimethyl-benz-yl)-1-phenyl-sulfonyl-1H-indol-2-yl]methyl-idene}propane-dioate.

In the title compound, C(32)H(33)NO(6)S, the indole ring system makes dihedral angles of 62.78 (10) and 80.53 (8)°, respectively, with the phenyl and benzene rings. In the crystal, the mol-ecules are linked through inter-molecular C-H⋯O hydrogen bonds, forming a chain along the a axis. Between the chains, a weak aromatic π-π stacking inter-action [centroid-centroid distance = 3.831 (2) Å] is observed.

Related literature

For the biological activity of indole derivatives, see: Ma et al. (2001 ▶); Zhao et al. (2002 ▶); Zhou et al. (2006 ▶). For related structures, see: Chakkaravarthi et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C32H33NO6S

M = 559.65

Triclinic,

a = 8.5103 (4) Å

b = 8.9540 (4) Å

c = 19.6546 (10) Å

α = 78.456 (3)°

β = 87.236 (4)°

γ = 86.736 (3)°

V = 1463.99 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.16 mm−1

T = 295 K

0.22 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.967, T max = 0.976

26660 measured reflections

7349 independent reflections

4328 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.211

S = 1.03

7349 reflections

370 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810019690/is2550sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019690/is2550Isup2.hkl

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

C32H33NO6S	Z = 2
Mr = 559.65	F(000) = 592
Triclinic, P1	Dx = 1.270 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5103 (4) Å	Cell parameters from 7772 reflections
b = 8.9540 (4) Å	θ = 2.4–24.3°
c = 19.6546 (10) Å	µ = 0.16 mm−1
α = 78.456 (3)°	T = 295 K
β = 87.236 (4)°	Block, colourless
γ = 86.736 (3)°	0.22 × 0.18 × 0.16 mm
V = 1463.99 (12) Å3

Bruker Kappa APEXII diffractometer	7349 independent reflections
Radiation source: fine-focus sealed tube	4328 reflections with I > 2σ(I)
graphite	Rint = 0.042
ω and φ scans	θmax = 28.5°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
Tmin = 0.967, Tmax = 0.976	k = −11→11
26660 measured reflections	l = −26→22

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.211	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.105P)2 + 0.4069P] where P = (Fo2 + 2Fc2)/3
7349 reflections	(Δ/σ)max < 0.001
370 parameters	Δρmax = 0.42 e Å−3
2 restraints	Δρmin = −0.31 e Å−3

	x	y	z	Uiso*/Ueq
S1	−0.00108 (7)	0.35985 (9)	0.37321 (3)	0.0626 (2)
O1	−0.0678 (2)	0.4651 (3)	0.41334 (11)	0.0837 (6)
O2	−0.0971 (2)	0.2939 (3)	0.33112 (10)	0.0790 (6)
O3	−0.0750 (3)	0.2569 (3)	0.11855 (14)	0.1099 (9)
O4	−0.1997 (3)	0.6190 (3)	0.21742 (15)	0.1050 (8)
O5	−0.1945 (3)	0.4863 (3)	0.08992 (14)	0.1139 (9)
O6	0.0438 (3)	0.6904 (2)	0.18672 (12)	0.0852 (6)
N1	0.1367 (2)	0.4543 (2)	0.31990 (10)	0.0526 (5)
C1	0.1061 (3)	0.2144 (3)	0.42788 (13)	0.0598 (6)
C2	0.1303 (4)	0.2243 (4)	0.49532 (16)	0.0859 (9)
H2	0.0909	0.3089	0.5126	0.103*
C3	0.2130 (5)	0.1083 (5)	0.5370 (2)	0.1025 (12)
H3	0.2274	0.1134	0.5831	0.123*
C4	0.2739 (5)	−0.0135 (5)	0.5118 (2)	0.1069 (13)
H4	0.3293	−0.0919	0.5406	0.128*
C5	0.2542 (6)	−0.0217 (4)	0.4438 (3)	0.1226 (16)
H5	0.2988	−0.1040	0.4261	0.147*
C6	0.1677 (5)	0.0930 (3)	0.40152 (18)	0.0889 (10)
H6	0.1518	0.0873	0.3556	0.107*
C7	0.2050 (3)	0.3920 (3)	0.26267 (12)	0.0489 (5)
C8	0.3634 (3)	0.4001 (2)	0.26078 (12)	0.0487 (5)
C9	0.4031 (3)	0.4704 (2)	0.31715 (12)	0.0490 (5)
C10	0.5466 (3)	0.5094 (3)	0.33863 (15)	0.0623 (6)
H10	0.6403	0.4902	0.3148	0.075*
C11	0.5468 (4)	0.5764 (3)	0.39536 (16)	0.0722 (8)
H11	0.6416	0.6032	0.4102	0.087*
C12	0.4072 (4)	0.6049 (3)	0.43112 (16)	0.0721 (8)
H12	0.4106	0.6489	0.4700	0.087*
C13	0.2652 (3)	0.5699 (3)	0.41068 (14)	0.0653 (7)
H13	0.1721	0.5906	0.4346	0.078*
C14	0.2644 (3)	0.5025 (3)	0.35296 (12)	0.0503 (5)
C15	0.1071 (3)	0.3562 (3)	0.20960 (13)	0.0563 (6)
C16	−0.0135 (3)	0.4425 (3)	0.18005 (13)	0.0592 (6)
C17	−0.0687 (4)	0.5916 (3)	0.19722 (14)	0.0671 (7)
C18	0.0018 (6)	0.8430 (4)	0.1979 (2)	0.1203 (15)
H19A	−0.1097	0.8655	0.1904	0.144*
H19B	0.0600	0.9163	0.1644	0.144*
C19	0.0364 (8)	0.8585 (6)	0.2684 (3)	0.161 (2)
H66A	−0.0292	0.7935	0.3014	0.241*
H66B	0.0159	0.9626	0.2730	0.241*
H66C	0.1451	0.8294	0.2769	0.241*
C20	−0.1044 (4)	0.4002 (4)	0.12446 (16)	0.0763 (8)
C21	−0.1577 (6)	0.2046 (7)	0.0635 (2)	0.1310 (17)
H21A	−0.1874	0.0999	0.0792	0.157*
H21B	−0.2520	0.2685	0.0512	0.157*
C22	−0.0463 (8)	0.2163 (10)	0.0041 (3)	0.191 (3)
H33A	0.0557	0.1769	0.0198	0.287*
H33B	−0.0402	0.3214	−0.0185	0.287*
H33C	−0.0812	0.1584	−0.0280	0.287*
C23	0.4831 (3)	0.3629 (3)	0.20674 (15)	0.0629 (7)
H23A	0.5870	0.3602	0.2253	0.076*
H23B	0.4785	0.4456	0.1665	0.076*
C24	0.4654 (3)	0.2139 (3)	0.18243 (12)	0.0514 (5)
C25	0.4139 (3)	0.2122 (3)	0.11623 (12)	0.0545 (6)
C26	0.4067 (3)	0.0728 (3)	0.09579 (14)	0.0637 (7)
H26	0.3716	0.0719	0.0518	0.076*
C27	0.4493 (3)	−0.0634 (3)	0.13816 (16)	0.0683 (7)
C28	0.5004 (4)	−0.0589 (3)	0.20301 (16)	0.0722 (8)
H28	0.5302	−0.1500	0.2324	0.087*
C29	0.5091 (3)	0.0768 (3)	0.22612 (13)	0.0606 (6)
C30	0.3701 (4)	0.3567 (3)	0.06561 (15)	0.0847 (9)
H30A	0.4612	0.4166	0.0538	0.127*
H30B	0.2894	0.4142	0.0865	0.127*
H30C	0.3319	0.3315	0.0244	0.127*
C31	0.4440 (5)	−0.2144 (4)	0.1150 (2)	0.1061 (13)
H31A	0.5475	−0.2632	0.1164	0.159*
H31B	0.4078	−0.1970	0.0685	0.159*
H31C	0.3732	−0.2789	0.1456	0.159*
C32	0.5710 (5)	0.0727 (5)	0.29715 (17)	0.0964 (11)
H32A	0.5875	−0.0314	0.3207	0.145*
H32B	0.4960	0.1244	0.3236	0.145*
H32C	0.6690	0.1227	0.2924	0.145*
H15	0.143 (4)	0.268 (4)	0.1932 (16)	0.085 (9)*

	U11	U22	U33	U12	U13	U23
S1	0.0375 (3)	0.0952 (5)	0.0569 (4)	0.0061 (3)	−0.0024 (3)	−0.0216 (3)
O1	0.0545 (11)	0.1244 (17)	0.0742 (13)	0.0296 (11)	0.0046 (9)	−0.0356 (12)
O2	0.0433 (10)	0.1292 (17)	0.0664 (11)	−0.0156 (10)	−0.0065 (8)	−0.0196 (12)
O3	0.116 (2)	0.123 (2)	0.1081 (18)	0.0088 (16)	−0.0507 (16)	−0.0572 (16)
O4	0.0776 (16)	0.0955 (16)	0.132 (2)	0.0165 (13)	0.0206 (15)	−0.0106 (15)
O5	0.114 (2)	0.134 (2)	0.0925 (17)	0.0064 (17)	−0.0521 (16)	−0.0129 (16)
O6	0.0803 (14)	0.0767 (13)	0.1012 (16)	−0.0048 (11)	−0.0096 (12)	−0.0222 (12)
N1	0.0419 (10)	0.0665 (12)	0.0531 (11)	0.0079 (9)	−0.0069 (8)	−0.0224 (9)
C1	0.0464 (13)	0.0751 (16)	0.0592 (14)	−0.0097 (12)	−0.0018 (11)	−0.0144 (12)
C2	0.082 (2)	0.112 (2)	0.0647 (18)	0.0148 (19)	−0.0113 (16)	−0.0244 (18)
C3	0.100 (3)	0.126 (3)	0.076 (2)	0.005 (2)	−0.025 (2)	−0.003 (2)
C4	0.112 (3)	0.079 (2)	0.117 (3)	−0.005 (2)	−0.026 (3)	0.016 (2)
C5	0.171 (5)	0.0572 (19)	0.136 (4)	0.013 (2)	−0.016 (3)	−0.014 (2)
C6	0.126 (3)	0.0638 (17)	0.080 (2)	−0.0078 (18)	−0.013 (2)	−0.0185 (16)
C7	0.0446 (12)	0.0520 (12)	0.0521 (12)	0.0033 (9)	−0.0016 (10)	−0.0168 (10)
C8	0.0460 (12)	0.0451 (11)	0.0557 (13)	0.0033 (9)	−0.0004 (10)	−0.0132 (10)
C9	0.0453 (12)	0.0443 (11)	0.0578 (13)	0.0030 (9)	−0.0075 (10)	−0.0111 (10)
C10	0.0492 (14)	0.0630 (15)	0.0762 (17)	−0.0023 (11)	−0.0088 (12)	−0.0160 (13)
C11	0.0664 (18)	0.0683 (16)	0.087 (2)	−0.0012 (13)	−0.0280 (15)	−0.0228 (15)
C12	0.081 (2)	0.0662 (16)	0.0774 (18)	0.0166 (14)	−0.0329 (16)	−0.0323 (14)
C13	0.0630 (16)	0.0722 (16)	0.0663 (16)	0.0201 (13)	−0.0149 (13)	−0.0305 (13)
C14	0.0471 (12)	0.0492 (12)	0.0571 (13)	0.0112 (10)	−0.0116 (10)	−0.0175 (10)
C15	0.0494 (13)	0.0685 (15)	0.0556 (14)	−0.0023 (11)	0.0002 (11)	−0.0243 (12)
C16	0.0516 (14)	0.0766 (16)	0.0496 (13)	−0.0056 (12)	−0.0022 (11)	−0.0121 (12)
C17	0.0627 (17)	0.0747 (17)	0.0579 (15)	0.0066 (14)	−0.0037 (13)	−0.0016 (13)
C18	0.129 (4)	0.080 (2)	0.152 (4)	0.010 (2)	−0.020 (3)	−0.025 (3)
C19	0.221 (7)	0.123 (4)	0.158 (5)	0.045 (4)	−0.067 (5)	−0.075 (3)
C20	0.0659 (18)	0.100 (2)	0.0638 (17)	−0.0061 (16)	−0.0127 (14)	−0.0151 (16)
C21	0.119 (4)	0.178 (5)	0.116 (3)	−0.015 (3)	−0.037 (3)	−0.069 (3)
C22	0.170 (6)	0.307 (9)	0.127 (4)	−0.039 (6)	−0.001 (4)	−0.109 (6)
C23	0.0544 (14)	0.0630 (14)	0.0751 (17)	−0.0084 (12)	0.0160 (12)	−0.0250 (13)
C24	0.0454 (12)	0.0514 (12)	0.0561 (13)	0.0037 (10)	0.0065 (10)	−0.0116 (10)
C25	0.0534 (13)	0.0565 (13)	0.0496 (13)	0.0071 (10)	0.0074 (10)	−0.0058 (10)
C26	0.0599 (15)	0.0753 (17)	0.0586 (15)	0.0010 (13)	0.0005 (12)	−0.0217 (13)
C27	0.0668 (17)	0.0553 (14)	0.0840 (19)	0.0031 (12)	0.0043 (14)	−0.0204 (14)
C28	0.0753 (19)	0.0520 (14)	0.082 (2)	0.0174 (13)	−0.0007 (15)	−0.0013 (13)
C29	0.0551 (14)	0.0650 (15)	0.0589 (15)	0.0131 (12)	−0.0055 (11)	−0.0092 (12)
C30	0.106 (3)	0.0739 (18)	0.0615 (17)	0.0176 (17)	0.0107 (16)	0.0080 (14)
C31	0.113 (3)	0.0680 (19)	0.146 (3)	−0.0031 (19)	0.008 (3)	−0.046 (2)
C32	0.096 (3)	0.117 (3)	0.074 (2)	0.029 (2)	−0.0270 (18)	−0.0164 (19)

S1—O2	1.420 (2)	C15—H15	0.94 (3)
S1—O1	1.424 (2)	C16—C17	1.487 (4)
S1—N1	1.682 (2)	C16—C20	1.488 (4)
S1—C1	1.755 (3)	C18—C19	1.465 (5)
O3—C20	1.320 (4)	C18—H19A	0.9700
O3—C21	1.483 (4)	C18—H19B	0.9700
O4—C17	1.194 (4)	C19—H66A	0.9600
O5—C20	1.190 (4)	C19—H66B	0.9600
O6—C17	1.321 (4)	C19—H66C	0.9600
O6—C18	1.449 (4)	C21—C22	1.458 (5)
N1—C14	1.422 (3)	C21—H21A	0.9700
N1—C7	1.438 (3)	C21—H21B	0.9700
C1—C6	1.363 (4)	C22—H33A	0.9600
C1—C2	1.372 (4)	C22—H33B	0.9600
C2—C3	1.370 (5)	C22—H33C	0.9600
C2—H2	0.9300	C23—C24	1.522 (3)
C3—C4	1.354 (6)	C23—H23A	0.9700
C3—H3	0.9300	C23—H23B	0.9700
C4—C5	1.371 (6)	C24—C29	1.392 (3)
C4—H4	0.9300	C24—C25	1.396 (3)
C5—C6	1.386 (5)	C25—C26	1.391 (3)
C5—H5	0.9300	C25—C30	1.506 (4)
C6—H6	0.9300	C26—C27	1.373 (4)
C7—C8	1.353 (3)	C26—H26	0.9300
C7—C15	1.460 (3)	C27—C28	1.375 (4)
C8—C9	1.441 (3)	C27—C31	1.514 (4)
C8—C23	1.508 (3)	C28—C29	1.387 (4)
C9—C14	1.391 (3)	C28—H28	0.9300
C9—C10	1.396 (3)	C29—C32	1.509 (4)
C10—C11	1.368 (4)	C30—H30A	0.9600
C10—H10	0.9300	C30—H30B	0.9600
C11—C12	1.389 (4)	C30—H30C	0.9600
C11—H11	0.9300	C31—H31A	0.9600
C12—C13	1.364 (4)	C31—H31B	0.9600
C12—H12	0.9300	C31—H31C	0.9600
C13—C14	1.388 (3)	C32—H32A	0.9600
C13—H13	0.9300	C32—H32B	0.9600
C15—C16	1.332 (4)	C32—H32C	0.9600
O2—S1—O1	120.54 (13)	C19—C18—H19B	109.4
O2—S1—N1	106.83 (11)	H19A—C18—H19B	108.0
O1—S1—N1	105.76 (13)	C18—C19—H66A	109.5
O2—S1—C1	109.32 (13)	C18—C19—H66B	109.5
O1—S1—C1	108.79 (13)	H66A—C19—H66B	109.5
N1—S1—C1	104.36 (11)	C18—C19—H66C	109.5
C20—O3—C21	116.6 (3)	H66A—C19—H66C	109.5
C17—O6—C18	117.1 (3)	H66B—C19—H66C	109.5
C14—N1—C7	106.24 (18)	O5—C20—O3	124.2 (3)
C14—N1—S1	115.80 (16)	O5—C20—C16	123.4 (3)
C7—N1—S1	120.08 (16)	O3—C20—C16	112.5 (3)
C6—C1—C2	120.7 (3)	C22—C21—O3	105.9 (4)
C6—C1—S1	118.6 (2)	C22—C21—H21A	110.5
C2—C1—S1	120.7 (2)	O3—C21—H21A	110.5
C3—C2—C1	119.4 (3)	C22—C21—H21B	110.5
C3—C2—H2	120.3	O3—C21—H21B	110.5
C1—C2—H2	120.3	H21A—C21—H21B	108.7
C4—C3—C2	120.6 (4)	C21—C22—H33A	109.5
C4—C3—H3	119.7	C21—C22—H33B	109.5
C2—C3—H3	119.7	H33A—C22—H33B	109.5
C3—C4—C5	120.2 (4)	C21—C22—H33C	109.5
C3—C4—H4	119.9	H33A—C22—H33C	109.5
C5—C4—H4	119.9	H33B—C22—H33C	109.5
C4—C5—C6	119.7 (4)	C8—C23—C24	116.5 (2)
C4—C5—H5	120.1	C8—C23—H23A	108.2
C6—C5—H5	120.1	C24—C23—H23A	108.2
C1—C6—C5	119.3 (3)	C8—C23—H23B	108.2
C1—C6—H6	120.4	C24—C23—H23B	108.2
C5—C6—H6	120.4	H23A—C23—H23B	107.3
C8—C7—N1	109.75 (19)	C29—C24—C25	119.5 (2)
C8—C7—C15	128.0 (2)	C29—C24—C23	119.0 (2)
N1—C7—C15	121.3 (2)	C25—C24—C23	121.5 (2)
C7—C8—C9	107.7 (2)	C26—C25—C24	118.9 (2)
C7—C8—C23	128.9 (2)	C26—C25—C30	119.0 (2)
C9—C8—C23	123.0 (2)	C24—C25—C30	122.1 (2)
C14—C9—C10	119.5 (2)	C27—C26—C25	122.4 (3)
C14—C9—C8	108.2 (2)	C27—C26—H26	118.8
C10—C9—C8	132.3 (2)	C25—C26—H26	118.8
C11—C10—C9	118.7 (3)	C26—C27—C28	117.6 (2)
C11—C10—H10	120.6	C26—C27—C31	122.1 (3)
C9—C10—H10	120.6	C28—C27—C31	120.2 (3)
C10—C11—C12	120.8 (3)	C27—C28—C29	122.3 (2)
C10—C11—H11	119.6	C27—C28—H28	118.9
C12—C11—H11	119.6	C29—C28—H28	118.9
C13—C12—C11	121.7 (3)	C28—C29—C24	119.3 (2)
C13—C12—H12	119.1	C28—C29—C32	119.1 (3)
C11—C12—H12	119.1	C24—C29—C32	121.6 (3)
C12—C13—C14	117.7 (3)	C25—C30—H30A	109.5
C12—C13—H13	121.1	C25—C30—H30B	109.5
C14—C13—H13	121.1	H30A—C30—H30B	109.5
C13—C14—C9	121.5 (2)	C25—C30—H30C	109.5
C13—C14—N1	130.4 (2)	H30A—C30—H30C	109.5
C9—C14—N1	108.11 (19)	H30B—C30—H30C	109.5
C16—C15—C7	126.1 (2)	C27—C31—H31A	109.5
C16—C15—H15	120.2 (19)	C27—C31—H31B	109.5
C7—C15—H15	113.4 (19)	H31A—C31—H31B	109.5
C15—C16—C17	124.2 (2)	C27—C31—H31C	109.5
C15—C16—C20	122.8 (3)	H31A—C31—H31C	109.5
C17—C16—C20	113.0 (2)	H31B—C31—H31C	109.5
O4—C17—O6	124.2 (3)	C29—C32—H32A	109.5
O4—C17—C16	123.9 (3)	C29—C32—H32B	109.5
O6—C17—C16	112.0 (2)	H32A—C32—H32B	109.5
O6—C18—C19	111.3 (4)	C29—C32—H32C	109.5
O6—C18—H19A	109.4	H32A—C32—H32C	109.5
C19—C18—H19A	109.4	H32B—C32—H32C	109.5
O6—C18—H19B	109.4
O2—S1—N1—C14	−167.56 (16)	C7—N1—C14—C13	−179.8 (3)
O1—S1—N1—C14	62.87 (18)	S1—N1—C14—C13	−43.7 (3)
C1—S1—N1—C14	−51.82 (18)	C7—N1—C14—C9	0.0 (2)
O2—S1—N1—C7	−37.8 (2)	S1—N1—C14—C9	136.08 (18)
O1—S1—N1—C7	−167.42 (17)	C8—C7—C15—C16	−124.3 (3)
C1—S1—N1—C7	77.89 (19)	N1—C7—C15—C16	42.8 (4)
O2—S1—C1—C6	40.3 (3)	C7—C15—C16—C17	−0.3 (4)
O1—S1—C1—C6	173.8 (2)	C7—C15—C16—C20	177.9 (2)
N1—S1—C1—C6	−73.7 (3)	C18—O6—C17—O4	−2.7 (5)
O2—S1—C1—C2	−141.1 (2)	C18—O6—C17—C16	176.6 (3)
O1—S1—C1—C2	−7.6 (3)	C15—C16—C17—O4	−122.4 (3)
N1—S1—C1—C2	104.9 (3)	C20—C16—C17—O4	59.2 (4)
C6—C1—C2—C3	−2.1 (5)	C15—C16—C17—O6	58.3 (4)
S1—C1—C2—C3	179.4 (3)	C20—C16—C17—O6	−120.1 (3)
C1—C2—C3—C4	1.6 (6)	C17—O6—C18—C19	94.3 (5)
C2—C3—C4—C5	0.4 (7)	C21—O3—C20—O5	1.9 (6)
C3—C4—C5—C6	−1.9 (7)	C21—O3—C20—C16	−178.8 (3)
C2—C1—C6—C5	0.6 (5)	C15—C16—C20—O5	−167.4 (3)
S1—C1—C6—C5	179.2 (3)	C17—C16—C20—O5	11.1 (4)
C4—C5—C6—C1	1.4 (7)	C15—C16—C20—O3	13.4 (4)
C14—N1—C7—C8	0.4 (3)	C17—C16—C20—O3	−168.2 (3)
S1—N1—C7—C8	−133.46 (18)	C20—O3—C21—C22	97.3 (6)
C14—N1—C7—C15	−168.9 (2)	C7—C8—C23—C24	−46.2 (4)
S1—N1—C7—C15	57.3 (3)	C9—C8—C23—C24	141.6 (2)
N1—C7—C8—C9	−0.6 (3)	C8—C23—C24—C29	−74.8 (3)
C15—C7—C8—C9	167.8 (2)	C8—C23—C24—C25	108.4 (3)
N1—C7—C8—C23	−173.7 (2)	C29—C24—C25—C26	0.4 (4)
C15—C7—C8—C23	−5.4 (4)	C23—C24—C25—C26	177.2 (2)
C7—C8—C9—C14	0.5 (3)	C29—C24—C25—C30	−177.9 (2)
C23—C8—C9—C14	174.2 (2)	C23—C24—C25—C30	−1.1 (4)
C7—C8—C9—C10	−178.5 (2)	C24—C25—C26—C27	−0.5 (4)
C23—C8—C9—C10	−4.9 (4)	C30—C25—C26—C27	177.9 (3)
C14—C9—C10—C11	1.0 (4)	C25—C26—C27—C28	0.1 (4)
C8—C9—C10—C11	−180.0 (2)	C25—C26—C27—C31	−178.8 (3)
C9—C10—C11—C12	0.2 (4)	C26—C27—C28—C29	0.3 (4)
C10—C11—C12—C13	−1.1 (5)	C31—C27—C28—C29	179.3 (3)
C11—C12—C13—C14	0.8 (4)	C27—C28—C29—C24	−0.3 (4)
C12—C13—C14—C9	0.4 (4)	C27—C28—C29—C32	−178.2 (3)
C12—C13—C14—N1	−179.9 (2)	C25—C24—C29—C28	0.0 (4)
C10—C9—C14—C13	−1.3 (4)	C23—C24—C29—C28	−176.9 (2)
C8—C9—C14—C13	179.5 (2)	C25—C24—C29—C32	177.8 (3)
C10—C9—C14—N1	178.9 (2)	C23—C24—C29—C32	0.9 (4)
C8—C9—C14—N1	−0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O4i	0.93	2.43	3.179 (4)	138
C13—H13···O1	0.93	2.48	3.030 (4)	118

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O4i	0.93	2.43	3.179 (4)	138

Symmetry code: (i) .