Ethyl 2-acetoxy­methyl-1-phenyl­sulfonyl-1H-indole-3-carboxyl­ate

Gunasekaran, B.; Sureshbabu, R.; Mohanakrishnan, A.K.; Chakkaravarthi, G.; Manivannan, V.

doi:10.1107/S1600536809029985

organic compounds

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Volume 65| Part 9| September 2009| Page o2069

doi:10.1107/S1600536809029985

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Ethyl 2-acetoxymethyl-1-phenylsulfonyl-1H-indole-3-carboxylate

B. Gunasekaran,^a Radhakrishnan Sureshbabu,^b A. K. Mohanakrishnan,^b G. Chakkaravarthi ^c and V. Manivannan ^d ^*

^aDepartment of Physics, AMET University, Kanathur, Chennai 603 112, 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: manivan_1999@yahoo.com

(Received 26 July 2009; accepted 28 July 2009; online 8 August 2009)

In the title compound, C₂₀H₁₉NO₆S, the phenyl ring of the phenylsulfonyl group makes a dihedral angle of 83.35 (5)° with the indole ring system. The molecular structure exhibits a number of short intramolecular C—H⋯O contacts.

Related literature

For the biological activity of indole derivatives, see: Andreani et al. (2001 ); Quetin-Leclercq (1994 ); Mukhopadhyay et al. (1981 ); Singh et al. (2000 ). For related structures, see: Chakkaravarthi et al. (2007 , 2008 ); Gunasekaran et al. (2009 ); For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₁₉NO₆S
M_r = 401.42
Orthorhombic, P b c a
a = 18.9097 (6) Å
b = 7.9737 (2) Å
c = 24.7877 (7) Å
V = 3737.50 (18) Å³
Z = 8
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 295 K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.949, T_max = 0.959
28247 measured reflections
5788 independent reflections
3533 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.153
S = 1.01
5788 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O5	0.93	2.57	3.446 (2)	157
C6—H6⋯O2	0.93	2.50	2.875 (3)	105
C8—H8⋯O2	0.93	2.42	2.993 (3)	120
C11—H11⋯O3	0.93	2.48	3.003 (3)	116
C18—H18A⋯O4	0.97	2.31	2.886 (3)	117
C18—H18B⋯O1	0.97	2.30	2.793 (3)	111

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: 10.1107/S1600536809029985/gk2226sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809029985/gk2226Isup2.hkl

checkCIF report

Comment top

Indole derivatives exhibit antibacterial, antifungal (Singh et al., 2000) and antitumour activities (Andreani et al., 2001). Some of the indole alkaloids extracted from plants possess interesting cytotoxic and antiparasitic properties (Quetin-Leclercq, 1994; Mukhopadhyay et al., 1981).

The geometric parameters of the title compound (Fig. 1) agree well with reported similar structures (Chakkaravarthi et al., 2007, 2008); (Gunasekaran et al., 2009). The phenyl ring makes a dihedral angle of 83.35 (5) ° with the indole ring system. The sum of the bond angles around N1 [356.99 (5)°] indicate the sp² hybridized state of atom N1 in the molecule.

A distorted tetrahedral geometry [O1—S1—O2 = 120.74 (10) ° and O1—S1—N1 = 106.73 (8) °] around S1 is observed. The widening of the angles may be due to repulsive interactions between the two short S=O bonds. The torsion angles O1—S1—N1—C14 and O2—S1—N1—C7 [20.02 (18) ° and -51.75 (15) ° respectively] indicate the syn conformation of sulfonyl moiety.

The molecular structure is stabilized by weak intramolecular C—H···O interactions. The C6—H6···O2 interaction generate an S(5) graph set motif. The C8—H8···O2, C11—H11···O3, C18—H18A···O4 & C18—H18B···O1 interactions generate S(6) graph set motif and C2—H2···O5 interaction generate an S(8) graph set motif. The C6—H6···O2 and C8—H8···O2 interactions together constitute a pair of bifurcated acceptor bonds generating a ring of graph set R₂¹(9) (Bernstein et al., 1995).

Related literature top

For the biological activity of indole derivatives, see: Andreani et al. (2001); Quetin-Leclercq (1994); Mukhopadhyay et al. (1981); Singh et al. (2000). For related structures, see: Chakkaravarthi et al. (2007, 2008); Gunasekaran et al. (2009); For graph-set notation, see: Bernstein et al. (1995)

Experimental top

Ethyl 2-(bromomethyl)-1-(phenylsulfonyl)-1H-indole-3-carboxylate (1 g, 2.4 mmol) was dissolved in dry dimethylformamide (10 ml). To this potassium acetate (0.47 g, 4.8 mmol) was added under nitrogen atmosphere. The reaction mixture was allowed to stir for 5 hr at room temperature. Then, the reaction mixture was poured over crushed ice (100 g) containing 1 mL of conc. HCl. The precipitated solid was filtered off and the solid was washed with water (3 x 20 ml) and dried. The product was recrystallized from methanol. Yield: 0.7 g (74%), m.p. 361–363K.

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 the title compound with atom labels and 30% probability displacement ellipsoids for non-H atoms.

Ethyl 2-acetoxymethyl-1-phenylsulfonyl-1H-indole-3-carboxylate top

Crystal data top

C₂₀H₁₉NO₆S	F(000) = 1680
M_r = 401.42	D_x = 1.427 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6552 reflections
a = 18.9097 (6) Å	θ = 2.7–27.1°
b = 7.9737 (2) Å	µ = 0.21 mm⁻¹
c = 24.7877 (7) Å	T = 295 K
V = 3737.50 (18) Å³	Block, colourless
Z = 8	0.25 × 0.20 × 0.20 mm

Data collection top

Bruker APEXII CCD diffractometer	5788 independent reflections
Radiation source: fine-focus sealed tube	3533 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 0 pixels mm^-1	θ_max = 31.6°, θ_min = 2.0°
ω and ϕ scans	h = −27→20
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→8
T_min = 0.949, T_max = 0.959	l = −36→36
28247 measured reflections

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0697P)² + 1.0858P] where P = (F_o² + 2F_c²)/3
5788 reflections	(Δ/σ)_max < 0.001
255 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₀H₁₉NO₆S	V = 3737.50 (18) Å³
M_r = 401.42	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 18.9097 (6) Å	µ = 0.21 mm⁻¹
b = 7.9737 (2) Å	T = 295 K
c = 24.7877 (7) Å	0.25 × 0.20 × 0.20 mm

Data collection top

Bruker APEXII CCD diffractometer	5788 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3533 reflections with I > 2σ(I)
T_min = 0.949, T_max = 0.959	R_int = 0.031
28247 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.01	Δρ_max = 0.28 e Å⁻³
5788 reflections	Δρ_min = −0.35 e Å⁻³
255 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.68111 (9)	0.2922 (2)	0.13401 (7)	0.0409 (4)
C2	0.66359 (10)	0.3751 (3)	0.18121 (7)	0.0483 (4)
H2	0.6165	0.3879	0.1913	0.058*
C3	0.71703 (11)	0.4382 (3)	0.21287 (8)	0.0541 (5)
H3	0.7062	0.4961	0.2444	0.065*
C4	0.78647 (11)	0.4159 (3)	0.19792 (9)	0.0558 (5)
H4	0.8224	0.4567	0.2199	0.067*
C5	0.80341 (11)	0.3345 (3)	0.15112 (9)	0.0552 (5)
H5	0.8506	0.3214	0.1413	0.066*
C6	0.75066 (11)	0.2720 (3)	0.11846 (8)	0.0483 (4)
H6	0.7617	0.2170	0.0865	0.058*
C7	0.60056 (10)	0.4924 (2)	0.03978 (6)	0.0428 (4)
C8	0.66197 (11)	0.4833 (3)	0.00964 (7)	0.0541 (5)
H8	0.6895	0.3868	0.0088	0.065*
C9	0.68026 (13)	0.6250 (3)	−0.01919 (8)	0.0637 (6)
H9	0.7214	0.6239	−0.0397	0.076*
C10	0.63942 (13)	0.7675 (3)	−0.01839 (8)	0.0625 (6)
H10	0.6535	0.8601	−0.0385	0.075*
C11	0.57857 (12)	0.7761 (3)	0.01128 (7)	0.0525 (5)
H11	0.5511	0.8729	0.0114	0.063*
C12	0.55875 (10)	0.6358 (2)	0.04138 (6)	0.0430 (4)
C13	0.49985 (10)	0.6010 (2)	0.07648 (6)	0.0413 (4)
C14	0.50652 (9)	0.4409 (2)	0.09542 (6)	0.0404 (4)
C15	0.44401 (11)	0.7252 (3)	0.08755 (7)	0.0494 (5)
C16	0.33828 (13)	0.7855 (4)	0.13344 (13)	0.0798 (8)
H16A	0.3227	0.8383	0.1002	0.096*
H16B	0.3533	0.8727	0.1582	0.096*
C17	0.28112 (17)	0.6899 (4)	0.15688 (15)	0.1048 (11)
H17A	0.2638	0.6106	0.1309	0.157*
H17B	0.2436	0.7644	0.1671	0.157*
H17C	0.2980	0.6313	0.1882	0.157*
C18	0.45723 (10)	0.3415 (3)	0.12950 (7)	0.0471 (4)
H18A	0.4095	0.3849	0.1262	0.057*
H18B	0.4573	0.2250	0.1182	0.057*
C19	0.45014 (11)	0.2553 (3)	0.22036 (8)	0.0537 (5)
C20	0.48239 (14)	0.2728 (4)	0.27501 (9)	0.0738 (7)
H20A	0.4577	0.2020	0.3001	0.111*
H20B	0.4789	0.3874	0.2866	0.111*
H20C	0.5312	0.2403	0.2735	0.111*
N1	0.56802 (8)	0.37097 (19)	0.07288 (6)	0.0430 (3)
O1	0.56787 (8)	0.10956 (18)	0.12805 (7)	0.0627 (4)
O2	0.64517 (9)	0.13016 (19)	0.04850 (6)	0.0663 (4)
O3	0.44205 (10)	0.8600 (2)	0.06699 (8)	0.0857 (6)
O4	0.39629 (8)	0.6727 (2)	0.12256 (6)	0.0641 (4)
O5	0.48159 (7)	0.35577 (17)	0.18482 (5)	0.0502 (3)
O6	0.40269 (11)	0.1643 (3)	0.20854 (7)	0.0913 (6)
S1	0.61405 (3)	0.20341 (6)	0.09468 (2)	0.04808 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0439 (9)	0.0323 (10)	0.0464 (8)	0.0010 (7)	−0.0041 (7)	0.0052 (7)
C2	0.0451 (10)	0.0481 (12)	0.0516 (9)	0.0023 (9)	0.0002 (8)	0.0016 (8)
C3	0.0603 (12)	0.0513 (13)	0.0508 (10)	−0.0009 (10)	−0.0050 (9)	−0.0036 (9)
C4	0.0541 (12)	0.0504 (13)	0.0631 (11)	−0.0073 (9)	−0.0138 (9)	0.0040 (9)
C5	0.0441 (10)	0.0516 (13)	0.0698 (12)	−0.0025 (9)	0.0003 (9)	0.0104 (10)
C6	0.0504 (10)	0.0405 (12)	0.0541 (9)	0.0027 (8)	0.0030 (8)	0.0026 (8)
C7	0.0524 (10)	0.0400 (11)	0.0359 (7)	−0.0054 (8)	−0.0076 (7)	−0.0011 (7)
C8	0.0604 (12)	0.0565 (13)	0.0454 (9)	−0.0010 (10)	0.0001 (8)	−0.0051 (9)
C9	0.0693 (14)	0.0767 (17)	0.0452 (10)	−0.0160 (12)	0.0061 (9)	−0.0028 (10)
C10	0.0826 (15)	0.0570 (15)	0.0478 (10)	−0.0208 (12)	−0.0024 (10)	0.0080 (9)
C11	0.0728 (13)	0.0397 (12)	0.0450 (9)	−0.0074 (9)	−0.0084 (9)	0.0026 (8)
C12	0.0551 (10)	0.0391 (11)	0.0348 (7)	−0.0054 (8)	−0.0106 (7)	−0.0035 (7)
C13	0.0491 (10)	0.0381 (10)	0.0366 (7)	−0.0010 (8)	−0.0114 (7)	−0.0010 (7)
C14	0.0420 (9)	0.0404 (11)	0.0389 (8)	−0.0030 (7)	−0.0104 (7)	0.0011 (7)
C15	0.0537 (11)	0.0463 (13)	0.0482 (9)	0.0039 (9)	−0.0120 (8)	0.0002 (8)
C16	0.0608 (14)	0.0734 (19)	0.1053 (19)	0.0158 (13)	0.0051 (14)	−0.0091 (15)
C17	0.084 (2)	0.087 (2)	0.144 (3)	0.0024 (17)	0.0415 (19)	−0.005 (2)
C18	0.0438 (9)	0.0490 (12)	0.0485 (9)	−0.0053 (8)	−0.0103 (7)	0.0048 (8)
C19	0.0529 (11)	0.0520 (13)	0.0562 (10)	−0.0001 (10)	0.0086 (9)	0.0086 (9)
C20	0.0858 (17)	0.0825 (18)	0.0532 (11)	−0.0016 (14)	0.0033 (11)	0.0150 (12)
N1	0.0468 (8)	0.0363 (9)	0.0459 (7)	−0.0002 (6)	−0.0071 (6)	0.0036 (6)
O1	0.0561 (8)	0.0387 (9)	0.0933 (11)	−0.0070 (6)	−0.0113 (8)	0.0163 (7)
O2	0.0780 (10)	0.0467 (9)	0.0743 (9)	0.0083 (7)	−0.0106 (8)	−0.0226 (7)
O3	0.0919 (13)	0.0588 (12)	0.1065 (14)	0.0256 (10)	0.0135 (11)	0.0258 (10)
O4	0.0605 (9)	0.0577 (10)	0.0741 (9)	0.0132 (7)	0.0094 (7)	0.0034 (8)
O5	0.0545 (8)	0.0515 (8)	0.0445 (6)	−0.0091 (6)	−0.0059 (6)	0.0084 (6)
O6	0.0865 (12)	0.1080 (15)	0.0792 (11)	−0.0482 (12)	0.0073 (10)	0.0148 (11)
S1	0.0519 (3)	0.0306 (3)	0.0617 (3)	0.0003 (2)	−0.0106 (2)	−0.0024 (2)

Geometric parameters (Å, º) top

C1—C6	1.380 (3)	C13—C15	1.473 (3)
C1—C2	1.384 (3)	C14—N1	1.406 (2)
C1—S1	1.7492 (18)	C14—C18	1.487 (3)
C2—C3	1.375 (3)	C15—O3	1.190 (3)
C2—H2	0.9300	C15—O4	1.320 (2)
C3—C4	1.376 (3)	C16—O4	1.444 (3)
C3—H3	0.9300	C16—C17	1.445 (4)
C4—C5	1.367 (3)	C16—H16A	0.9700
C4—H4	0.9300	C16—H16B	0.9700
C5—C6	1.378 (3)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—H6	0.9300	C17—H17C	0.9600
C7—C8	1.383 (3)	C18—O5	1.451 (2)
C7—C12	1.390 (3)	C18—H18A	0.9700
C7—N1	1.411 (2)	C18—H18B	0.9700
C8—C9	1.380 (3)	C19—O6	1.190 (3)
C8—H8	0.9300	C19—O5	1.331 (2)
C9—C10	1.374 (4)	C19—C20	1.492 (3)
C9—H9	0.9300	C20—H20A	0.9600
C10—C11	1.367 (3)	C20—H20B	0.9600
C10—H10	0.9300	C20—H20C	0.9600
C11—C12	1.396 (3)	N1—S1	1.6838 (16)
C11—H11	0.9300	O1—S1	1.4166 (15)
C12—C13	1.440 (3)	O2—S1	1.4136 (16)
C13—C14	1.366 (3)

C6—C1—C2	121.34 (17)	O3—C15—O4	123.1 (2)
C6—C1—S1	119.21 (14)	O3—C15—C13	123.3 (2)
C2—C1—S1	119.39 (14)	O4—C15—C13	113.56 (17)
C3—C2—C1	118.77 (18)	O4—C16—C17	108.4 (2)
C3—C2—H2	120.6	O4—C16—H16A	110.0
C1—C2—H2	120.6	C17—C16—H16A	110.0
C2—C3—C4	120.01 (19)	O4—C16—H16B	110.0
C2—C3—H3	120.0	C17—C16—H16B	110.0
C4—C3—H3	120.0	H16A—C16—H16B	108.4
C5—C4—C3	120.91 (19)	C16—C17—H17A	109.5
C5—C4—H4	119.5	C16—C17—H17B	109.5
C3—C4—H4	119.5	H17A—C17—H17B	109.5
C4—C5—C6	120.04 (19)	C16—C17—H17C	109.5
C4—C5—H5	120.0	H17A—C17—H17C	109.5
C6—C5—H5	120.0	H17B—C17—H17C	109.5
C5—C6—C1	118.91 (18)	O5—C18—C14	107.23 (14)
C5—C6—H6	120.5	O5—C18—H18A	110.3
C1—C6—H6	120.5	C14—C18—H18A	110.3
C8—C7—C12	122.42 (18)	O5—C18—H18B	110.3
C8—C7—N1	130.14 (18)	C14—C18—H18B	110.3
C12—C7—N1	107.44 (16)	H18A—C18—H18B	108.5
C9—C8—C7	116.6 (2)	O6—C19—O5	122.7 (2)
C9—C8—H8	121.7	O6—C19—C20	126.1 (2)
C7—C8—H8	121.7	O5—C19—C20	111.21 (19)
C10—C9—C8	121.9 (2)	C19—C20—H20A	109.5
C10—C9—H9	119.1	C19—C20—H20B	109.5
C8—C9—H9	119.1	H20A—C20—H20B	109.5
C11—C10—C9	121.5 (2)	C19—C20—H20C	109.5
C11—C10—H10	119.3	H20A—C20—H20C	109.5
C9—C10—H10	119.3	H20B—C20—H20C	109.5
C10—C11—C12	118.2 (2)	C14—N1—C7	108.65 (15)
C10—C11—H11	120.9	C14—N1—S1	127.94 (12)
C12—C11—H11	120.9	C7—N1—S1	120.40 (13)
C7—C12—C11	119.40 (18)	C15—O4—C16	116.42 (19)
C7—C12—C13	107.40 (16)	C19—O5—C18	115.88 (15)
C11—C12—C13	133.20 (19)	O2—S1—O1	120.74 (10)
C14—C13—C12	108.42 (16)	O2—S1—N1	106.44 (9)
C14—C13—C15	129.06 (18)	O1—S1—N1	106.73 (8)
C12—C13—C15	122.52 (17)	O2—S1—C1	108.47 (9)
C13—C14—N1	108.09 (16)	O1—S1—C1	109.60 (9)
C13—C14—C18	129.45 (17)	N1—S1—C1	103.45 (8)
N1—C14—C18	122.22 (16)

C6—C1—C2—C3	0.1 (3)	C12—C13—C15—O4	−177.13 (16)
S1—C1—C2—C3	177.33 (15)	C13—C14—C18—O5	−97.2 (2)
C1—C2—C3—C4	−1.1 (3)	N1—C14—C18—O5	89.02 (19)
C2—C3—C4—C5	1.5 (3)	C13—C14—N1—C7	0.88 (18)
C3—C4—C5—C6	−0.7 (3)	C18—C14—N1—C7	175.80 (14)
C4—C5—C6—C1	−0.4 (3)	C13—C14—N1—S1	160.98 (12)
C2—C1—C6—C5	0.7 (3)	C18—C14—N1—S1	−24.1 (2)
S1—C1—C6—C5	−176.58 (15)	C8—C7—N1—C14	179.48 (17)
C12—C7—C8—C9	0.1 (3)	C12—C7—N1—C14	−0.79 (18)
N1—C7—C8—C9	179.75 (17)	C8—C7—N1—S1	17.6 (2)
C7—C8—C9—C10	−0.5 (3)	C12—C7—N1—S1	−162.66 (12)
C8—C9—C10—C11	0.2 (3)	O3—C15—O4—C16	2.7 (3)
C9—C10—C11—C12	0.4 (3)	C13—C15—O4—C16	−177.34 (18)
C8—C7—C12—C11	0.6 (3)	C17—C16—O4—C15	160.9 (2)
N1—C7—C12—C11	−179.20 (14)	O6—C19—O5—C18	−3.3 (3)
C8—C7—C12—C13	−179.84 (16)	C20—C19—O5—C18	176.40 (18)
N1—C7—C12—C13	0.40 (18)	C14—C18—O5—C19	−170.56 (16)
C10—C11—C12—C7	−0.8 (3)	C14—N1—S1—O2	150.20 (15)
C10—C11—C12—C13	179.76 (18)	C7—N1—S1—O2	−51.75 (15)
C7—C12—C13—C14	0.13 (18)	C14—N1—S1—O1	20.02 (18)
C11—C12—C13—C14	179.66 (18)	C7—N1—S1—O1	178.06 (13)
C7—C12—C13—C15	−179.64 (15)	C14—N1—S1—C1	−95.58 (16)
C11—C12—C13—C15	−0.1 (3)	C7—N1—S1—C1	62.47 (14)
C12—C13—C14—N1	−0.62 (18)	C6—C1—S1—O2	−4.02 (18)
C15—C13—C14—N1	179.14 (16)	C2—C1—S1—O2	178.69 (15)
C12—C13—C14—C18	−175.05 (16)	C6—C1—S1—O1	129.69 (16)
C15—C13—C14—C18	4.7 (3)	C2—C1—S1—O1	−47.59 (17)
C14—C13—C15—O3	−176.9 (2)	C6—C1—S1—N1	−116.77 (15)
C12—C13—C15—O3	2.8 (3)	C2—C1—S1—N1	65.94 (16)
C14—C13—C15—O4	3.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O5	0.93	2.57	3.446 (2)	157
C6—H6···O2	0.93	2.50	2.875 (3)	105
C8—H8···O2	0.93	2.42	2.993 (3)	120
C11—H11···O3	0.93	2.48	3.003 (3)	116
C18—H18A···O4	0.97	2.31	2.886 (3)	117
C18—H18B···O1	0.97	2.30	2.793 (3)	111

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉NO₆S
M_r	401.42
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	295
a, b, c (Å)	18.9097 (6), 7.9737 (2), 24.7877 (7)
V (Å³)	3737.50 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.949, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	28247, 5788, 3533
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.737

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.153, 1.01
No. of reflections	5788
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.35

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
C2—H2···O5	0.93	2.57	3.446 (2)	157
C6—H6···O2	0.93	2.50	2.875 (3)	105
C8—H8···O2	0.93	2.42	2.993 (3)	120
C11—H11···O3	0.93	2.48	3.003 (3)	116
C18—H18A···O4	0.97	2.31	2.886 (3)	117
C18—H18B···O1	0.97	2.30	2.793 (3)	111

Acknowledgements

BG thanks AMET University management, India, for their kind support.

References

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