Diethyl 2-{[3-(2,4,6-trimethyl­benz­yl)-1-phenyl­sulfonyl-1H-indol-2-yl]methyl­idene}propane­dioate

Saravanan, B.; Dhayalan, V.; Mohanakrishnan, A.K.; Chakkaravarthi, G.; Manivannan, V.

doi:10.1107/S1600536810019690

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1509

https://doi.org/10.1107/S1600536810019690

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Diethyl 2-{[3-(2,4,6-trimethylbenzyl)-1-phenylsulfonyl-1H-indol-2-yl]methylidene}propanedioate

B. Saravanan,^a V. Dhayalan,^b A. K. Mohanakrishnan,^b G. Chakkaravarthi ^c and V. Manivannan ^d ^*

^aDepartment of Physics, J. J. College of Arts and Science, Pudukkottai 622 422, Tamil Nadu, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, ^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and ^dDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
^*Correspondence e-mail: manivan1948@yahoo.com

(Received 15 May 2010; accepted 25 May 2010; online 29 May 2010)

In the title compound, C₃₂H₃₃NO₆S, 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 molecules are linked through intermolecular C—H⋯O hydrogen bonds, forming a chain along the a axis. Between the chains, a weak aromatic π–π stacking interaction [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_r = 559.65
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.062
wR(F²) = 0.211
S = 1.03
7349 reflections
370 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.31 e Å⁻³

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) x+1, y, z.

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810019690/is2550Isup2.hkl

checkCIF report

Comment top

Indole derivatives are found to possess anticancer, antimalarial and antihypertensive activities (Ma et al., 2001; Zhou et al., 2006; Zhao et al., 2002). In continuation of our studies in indole derivatives, we report the crystal structure of the title compound, (I). The geometric parameters of (I) (Fig. 1) agree with those in the reported structures (Chakkaravarthi et al., 2007, 2008).

The nine-membered indole ring system forms dihedral angles of 62.78 (10) and 80.53 (8)° with the phenyl ring (C1–C6) and benzene ring (C24–C29), respectively. The torsion angles O2—S1—N1—C7 and O1—S1—N1—C14 [-37.8 (2)° and 62.87 (18)°, respectively] indicate the syn-conformation of the sulfonyl moiety. The sum of the bond angles around N1 [342.1 (2)°] indicates that N1 is sp³-hybridized.

The molecular structure is stabilized by a weak intramolecular C—H···O interaction and the crystal packing of (I) (Fig. 2) exhibits weak intermolecular C—H···O (Table 1) and π–π interactions [Cg···Cg (-x, -y, 1-z) distance of 3.831 (2) Å]; Cg is the centroid of the C1–C6 ring.

Related literature top

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 top

To a solution of diethyl-2-((3-(bromomethyl)-1-(phenylsulfonyl) -1H-indol-2-yl)methylene)malonate (0.3 g, 0.57 mmol) in dry 1,2-dichloroethane (15 ml), anhydrous ZnBr₂ (0.25 g, 1.11 mmol) and mesitylene (0.19 ml, 1.41 mmol) were added. It was then refluxed for 4 h under N₂ atmosphere. The solvent was removed and the residue was quenched with ice-water (50 ml) containing 1 ml of conc. HCl, extracted with chloroform (2 × 10 ml) and dried (Na₂SO₄). Removal of solvent followed by flash column chromatographic purification (n-hexane/ethyl acetate 98:2) led to the isolation of product as a colourless crystal.

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); 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: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), viewed down the c axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

Diethyl 2-{[3-(2,4,6-trimethylbenzyl)-1-phenylsulfonyl- 1H-indol-2-yl]methylidene}propanedioate top

Crystal data top

C₃₂H₃₃NO₆S	Z = 2
M_r = 559.65	F(000) = 592
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.062	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(F_o²) + (0.105P)² + 0.4069P] where P = (F_o² + 2F_c²)/3
7349 reflections	(Δ/σ)_max < 0.001
370 parameters	Δρ_max = 0.42 e Å⁻³
2 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₃₂H₃₃NO₆S	γ = 86.736 (3)°
M_r = 559.65	V = 1463.99 (12) Å³
Triclinic, P1	Z = 2
a = 8.5103 (4) Å	Mo Kα radiation
b = 8.9540 (4) Å	µ = 0.16 mm⁻¹
c = 19.6546 (10) Å	T = 295 K
α = 78.456 (3)°	0.22 × 0.18 × 0.16 mm
β = 87.236 (4)°

Data collection top

Bruker Kappa APEXII diffractometer	7349 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4328 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.976	R_int = 0.042
26660 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	2 restraints
wR(F²) = 0.211	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.42 e Å⁻³
7349 reflections	Δρ_min = −0.31 e Å⁻³
370 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₃₂H₃₃NO₆S
M_r	559.65
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.5103 (4), 8.9540 (4), 19.6546 (10)
α, β, γ (°)	78.456 (3), 87.236 (4), 86.736 (3)
V (Å³)	1463.99 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.22 × 0.18 × 0.16

Data collection
Diffractometer	Bruker Kappa APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.967, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	26660, 7349, 4328
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.672

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.211, 1.03
No. of reflections	7349
No. of parameters	370
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.31

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z.

Acknowledgements

The authors wish to acknowledge DV University of Madras for the data collection.

References

Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3698. Web of Science CSD CrossRef IUCr Journals Google Scholar
Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ma, C., Liu, X., Li, X., Flippen-Anderson, J., Yu, S. & Cook, J. M. (2001). J. Org. Chem. 66, 4525–4542. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhao, S., Liao, X. & Cook, J. M. (2002). Org. Lett. 4, 687–690. Web of Science CrossRef PubMed CAS Google Scholar
Zhou, H., Liao, X., Yin, W., Ma, J. & Cook, J. M. (2006). J. Org. Chem. 71, 251–259. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 66| Part 6| June 2010| Page o1509

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di­ethyl 2-{[3-(2,4,6-tri­methyl­benz­yl)-1-phenyl­sulfonyl-1H-indol-2-yl]methyl­­idene}propane­dioate

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Experimental

Crystal data

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Refinement

Supporting information

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organic compounds

Diethyl 2-{[3-(2,4,6-trimethylbenzyl)-1-phenylsulfonyl-1H-indol-2-yl]methylidene}propanedioate