Diethyl 2-[(2-benzyl-1-phenyl­sulfonyl-1H-indol-3-yl)methyl­ene]malonate

Kavitha, T.; Thenmozhi, M.; Dhayalan, V.; Mohanakrishnan, A.K.; Ponnuswamy, M.N.

doi:10.1107/S160053680804004X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o12

doi:10.1107/S160053680804004X

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Diethyl 2-[(2-benzyl-1-phenylsulfonyl-1H-indol-3-yl)methylene]malonate

T. Kavitha,^a M. Thenmozhi,^a V. Dhayalan,^b A. K. Mohanakrishnan ^b and M. N. Ponnuswamy ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600025, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600025, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 18 November 2008; accepted 27 November 2008; online 3 December 2008)

In the title compound, C₂₉H₂₇NO₆S, the sulfonyl-bound phenyl ring is almost perpendicular to the indole ring system [dihedral angle = 87.96 (6)°], while the benzylphenyl ring is oriented at an angle of 76.8 (7)°. An intramolecular C—H⋯O hydrogen bond is observed. In the crystal structure, molecules are linked into a zigzag C(10) chain along the b axis by intermolecular 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_r = 517.58
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.142
S = 1.02
7583 reflections
334 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.27 e Å⁻³

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) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

Indole derivatives have been found to exhibit antibacterial, antifungal (Wang & Ng, 2002; Singh et al., 2000; Tsotinis et al., 1997; Quetin-Leclercq et al., 1995) and antitumour activities (Andreani et al., 2001).

The longer C—N distances [N1—C2 = 1.417 (2) Å and N1—C5 = 1.421 (2) Å] are indicative of the electronic withdrawing character of the phenylsulfonyl group. Atom S1 has a distorted tetrahedral configuration. The widening of the O1—S1—O2 angle to 120.09 (8)°, and the resultant narrowing of the N1—S1—C10 to 104.99 (8)°, from the ideal tetrahedral values, are attributed to the Thorpe- Ingold effect (Bassindale, 1984). The indole ring system is planar. The sum of bond angles around N1 (358.0°) indicates that N1 is in sp² hybridization. The sulfonyl bound phenyl ring is almost perpendicular to the indole ring system, with a dihedral angle of 87.96 (6)°. The benzylphenyl ring is oriented at an angle of 76.69 (5)° with respect to the indole ring system. The ester groups attached to the indole ring system assume extended conformations [C3—C23—C24—C25 = 178.7 (2)°, C23—C24—C25—O4 = -176.8 (2)°, C24—C25—O4—C26 =179.4 (2)°, C25—O4—C26—C27 = 172.6 (2)°]. An intramolecular C6—H6···O1 hydrogen bond is observed.

In the crystal structure, the molecules are linked into a zigzag C(10) chain along the b axis by intermolecular C—H···O hydrogen bonds (Table 1 and Fig.2).

Related literature top

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 top

To a solution of diethyl-2-((2-(bromomethyl)-1-(phenylsulfonyl)-1H-indol-3-yl)methylene)malonate (0.5 g, 0.96 mmol) in dry benzene (15 ml), ZnBr₂ (0.43 g, 1.90 mmol) was added. The reaction mixture was then refluxed for 5 h under N₂ atmosphere. It was then poured over ice-water (50 ml) containing 1 ml of concentrated HCl, extracted with chloroform (2 × 10 ml) and dried (Na₂SO₄). Removal of solvent followed by flash column chromatography (silica gel, 230–420 mesh, n-hexane/ethyl acetate 99:1) led to the isolation of diethyl-2-((2-benzyl-1-(phenylsulfonyl)-1H-indol-3-yl)methylene)malonate as a colourless solid. Single crystals were obtained by recrystallization from CDCl₃.

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: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 20% probability level. H atoms have been omitted for clarity.
	Fig. 2. Crystal packing of the title compound. H atoms not involved in hydrogen bonding have been omitted.

Diethyl 2-[(2-benzyl-1-phenylsulfonyl-1H-indol-3-yl)methylene]malonate top

Crystal data top

C₂₉H₂₇NO₆S	F(000) = 1088
M_r = 517.58	D_x = 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

Data collection top

Bruker Kappa APEXII area-detector diffractometer	7583 independent reflections
Radiation source: fine-focus sealed tube	4683 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω and ϕ scans	θ_max = 29.9°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −15→12
T_min = 0.952, T_max = 0.968	k = −14→19
34168 measured reflections	l = −22→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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0628P)² + 0.5537P] where P = (F_o² + 2F_c²)/3
7583 reflections	(Δ/σ)_max = 0.021
334 parameters	Δρ_max = 0.25 e Å⁻³
1 restraint	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₉H₂₇NO₆S	V = 2637.1 (4) Å³
M_r = 517.58	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.8280 (9) Å	µ = 0.17 mm⁻¹
b = 13.7762 (11) Å	T = 293 K
c = 17.6832 (16) Å	0.30 × 0.25 × 0.16 mm
β = 91.341 (4)°

Data collection top

Bruker Kappa APEXII area-detector diffractometer	7583 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	4683 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.968	R_int = 0.030
34168 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	1 restraint
wR(F²) = 0.142	H-atom parameters constrained
S = 1.02	Δρ_max = 0.25 e Å⁻³
7583 reflections	Δρ_min = −0.27 e Å⁻³
334 parameters

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	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₉H₂₇NO₆S
M_r	517.58
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.8280 (9), 13.7762 (11), 17.6832 (16)
β (°)	91.341 (4)
V (Å³)	2637.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.30 × 0.25 × 0.16

Data collection
Diffractometer	Bruker Kappa APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.952, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	34168, 7583, 4683
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.701

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.142, 1.02
No. of reflections	7583
No. of parameters	334
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.27

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

TK thanks Dr Babu Varghese, SAIF, IIT-Madras, Chennai, India, for his help with the data collection. VD thanks UGC, India, for financial support.

References

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