(3-Phenyl­sulfanyl-1-phenyl­sulfonyl-1H-indol-2-yl)methyl acetate

Rammohan, A.; Govindan, E.; SubbiahPandi, A.; Sureshbabu, R.; Mohana Krishnan, A.K.

doi:10.1107/S1600536811014802

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages o1240-o1241

doi:10.1107/S1600536811014802

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(3-Phenylsulfanyl-1-phenylsulfonyl-1H-indol-2-yl)methyl acetate

Alagappa Rammohan,^a E. Govindan,^a A. SubbiahPandi,^a ^* R. Sureshbabu ^b and A. K. Mohana Krishnan ^b

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: a_sp59@yahoo.in

(Received 11 April 2011; accepted 20 April 2011; online 29 April 2011)

In the title compound, C₂₃H₁₉NO₄S₂, the indole ring system makes dihedral angles of 89.6 (1) and 84.5 (8)° with the phenylsulfonyl and phenylsulfanyl rings, respectively. In the crystal, the molecules are linked into C(10) chains running along the c axis by an intermolecular C—H⋯O hydrogen bond. In addition, the crystal packing is stabilized by C—H⋯π interactions.

Related literature

For biological activities of indole derivatives, see: Singh et al. (2000 ); Andreani et al. (2001 ); Quetin-Leclercq (1994 ); Mukhopadhyay et al. (1981 ); Taylor et al. (1999 ); Williams et al. (1993 ); Sivaraman et al. (1996 ). For related structures, see: Ravishankar et al. (2005 ); Chakkaravarthi et al. (2008 ). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₃H₁₉NO₄S₂
M_r = 437.51
Monoclinic, P 2₁ /c
a = 14.6530 (6) Å
b = 9.4482 (4) Å
c = 15.2461 (7) Å
β = 97.055 (3)°
V = 2094.76 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.981, T_max = 0.985
19397 measured reflections
5235 independent reflections
3638 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.104
S = 1.03
5235 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1/C1/C6–C8 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O4ⁱ	0.93	2.59	3.274 (2)	131
C15—H15⋯Cg1ⁱⁱ	0.93	2.77	3.559 (2)	143
C16—H16⋯Cg2ⁱⁱ	0.93	2.72	3.5146 (19)	143
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014802/bt5514sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811014802/bt5514Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811014802/bt5514Isup3.cml

checkCIF report

Comment top

Indole derivatives have been found to 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, antitumour or antiparasitic properties (Quetin-Leclercq, 1994; Mukhopadhyay et al., 1981). Pyrido[1,2-a]indole derivatives have been identified as potent inhibitors of human immunodeficiency virus type 1 (Taylor et al., 1999), and 5-chloro-3-(phenylsulfonyl)indole-2-carboxamide is reported to be a highly potent non-nucleoside inhibitor of HIV-1 reverse transcriptase (Williams et al.,1993). The interaction of phenylsulfonylindole with calf thymus DNA has also been studied by spectroscopic methods (Sivaraman et al., 1996). Against this background, and in order to obtain detailed information on molecular conformations in the solid state, X-ray studies of the title compound (I) have been carried out.

X-Ray analysis confirms the molecular structure and atom connectivity for (I), as illustrated in Fig. 1. The indole ring system is essentially planar, with maximum deviation of 0.020 (2) Å for atom N1. The mean planes of the indole ring system make a dihedral algles of 89.6 (1) and 84.5 (8)° with respect to the phenyl rings, it shows that both the phenyl rings are perpendicular with respect to the indole ring system. The S—O, S—C, and S—N distances are 1.420 (12), 1.754 (17) and 1.676 (14) Å, respectively, these are comparable as observed in similar structures (Ravishankar et al., 2005). As a result of the electron-withdrawing character of the phenylsulfonyl group, the N—Csp² bond lengths, viz. N1—C1 [1.422 (2) Å] and N1—C8 [1.418 (2) Å], are longer than the mean value of 1.355 (14) Å reported for N atoms with planar configurations.

The S atom exhibits significant deviation from that of a regular tetrahedron, with the largest deviations being seen for the O—S—O [O1—S1—O2 120.3 (7)°] and O—S—N angles [O1—S1—N1 105.4 (7)°]. The widening of the angles may be due to repulsive interactions between the two short S═O bonds, similar to what is observed in related structures (Chakkaravarthi et al., 2008). The atom C4 act as a donor to the atom O4 of the neighbouring molecule at (x, 3/2 - y, 1/2 + z). This hydrogen bond is involved in a motif C(10) chain along b axis. In addition to van der Waals interaction, the crystal packing is stabilized by C—H..O and C—H···π interactions.

Related literature top

For biological activities of idole derivatives, see: Singh et al. (2000); Andreani et al. (2001); Quetin-Leclercq (1994); Mukhopadhyay et al. (1981); Taylor et al. (1999); Williams et al. (1993); Sivaraman et al. (1996). For related structures, see: Ravishankar et al. (2005); Chakkaravarthi et al. (2008). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995).

Experimental top

To solution of 2-(bromomethyl)-1-(phenyl sulfonyl)-3-(phenylthio)-1H-indole (2.18 mmol) in dry dimethyl formamide (10 ml), potassium acetate (4.36 mmol) was added under nitrogen atmosphere, the reaction mixture was stirred at room temperature for 5 h, then it was poured over crushed ice (50 g) containing 1 ml of concentrated hydrochloric acid. The obtained brown solid was filtered and dried. Single crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a solution in methanol.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (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, 2009).

Figures top

	Fig. 1. View of the title molecule with the atom labeling scheme. The displacement ellipsoids are drawn at the 30% probability level while the H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The molecular packing viewed down the b axis.

(3-Phenylsulfanyl-1-phenylsulfonyl-1H-indol-2-yl)methyl acetate top

Crystal data top

C₂₃H₁₉NO₄S₂	F(000) = 912
M_r = 437.51	D_x = 1.387 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5235 reflections
a = 14.6530 (6) Å	θ = 1.4–28.4°
b = 9.4482 (4) Å	µ = 0.29 mm⁻¹
c = 15.2461 (7) Å	T = 293 K
β = 97.055 (3)°	Block, white
V = 2094.76 (16) Å³	0.25 × 0.22 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	5235 independent reflections
Radiation source: fine-focus sealed tube	3638 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and ϕ scans	θ_max = 28.4°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
T_min = 0.981, T_max = 0.985	k = −11→12
19397 measured reflections	l = −20→20

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0433P)² + 0.4791P] where P = (F_o² + 2F_c²)/3
5235 reflections	(Δ/σ)_max < 0.001
272 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₃H₁₉NO₄S₂	V = 2094.76 (16) Å³
M_r = 437.51	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.6530 (6) Å	µ = 0.29 mm⁻¹
b = 9.4482 (4) Å	T = 293 K
c = 15.2461 (7) Å	0.25 × 0.22 × 0.19 mm
β = 97.055 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5235 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3638 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.985	R_int = 0.027
19397 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.03	Δρ_max = 0.26 e Å⁻³
5235 reflections	Δρ_min = −0.29 e Å⁻³
272 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
C1	0.16888 (11)	0.62556 (16)	0.35882 (10)	0.0387 (4)
C2	0.09311 (12)	0.55131 (18)	0.38072 (11)	0.0463 (4)
H2	0.0349	0.5645	0.3500	0.056*
C3	0.10805 (13)	0.45722 (19)	0.44998 (12)	0.0530 (4)
H3	0.0586	0.4057	0.4660	0.064*
C4	0.19466 (14)	0.43671 (19)	0.49671 (12)	0.0543 (5)
H4	0.2019	0.3728	0.5434	0.065*
C5	0.26938 (13)	0.50947 (18)	0.47475 (11)	0.0482 (4)
H5	0.3273	0.4959	0.5061	0.058*
C6	0.25666 (11)	0.60461 (16)	0.40419 (10)	0.0410 (4)
C7	0.31844 (11)	0.69850 (17)	0.36612 (11)	0.0424 (4)
C8	0.27026 (11)	0.77336 (17)	0.30037 (11)	0.0422 (4)
C9	0.30417 (12)	0.89164 (18)	0.24908 (12)	0.0494 (4)
H9A	0.3708	0.8898	0.2536	0.059*
H9B	0.2795	0.8842	0.1872	0.059*
C10	0.28751 (13)	1.14037 (19)	0.24295 (13)	0.0534 (4)
C11	0.2490 (2)	1.2651 (2)	0.28528 (19)	0.0882 (8)
H11A	0.2619	1.3495	0.2540	0.132*
H11B	0.2765	1.2722	0.3456	0.132*
H11C	0.1837	1.2541	0.2836	0.132*
C12	0.07661 (13)	0.49985 (18)	0.14300 (12)	0.0522 (4)
H12	0.0490	0.4775	0.1930	0.063*
C13	0.08604 (15)	0.3989 (2)	0.08013 (13)	0.0622 (5)
H13	0.0656	0.3071	0.0880	0.075*
C14	0.12545 (14)	0.4326 (2)	0.00578 (13)	0.0600 (5)
H14	0.1311	0.3637	−0.0368	0.072*
C15	0.15663 (14)	0.5672 (2)	−0.00607 (12)	0.0598 (5)
H15	0.1831	0.5894	−0.0567	0.072*
C16	0.14880 (12)	0.66998 (19)	0.05698 (11)	0.0506 (4)
H16	0.1703	0.7612	0.0495	0.061*
C17	0.10864 (10)	0.63531 (16)	0.13106 (10)	0.0391 (3)
C18	0.43670 (12)	0.7939 (2)	0.50554 (13)	0.0557 (5)
C19	0.39555 (14)	0.9229 (3)	0.51322 (15)	0.0681 (6)
H19	0.3656	0.9675	0.4634	0.082*
C20	0.39877 (17)	0.9870 (3)	0.59577 (18)	0.0861 (8)
H20	0.3692	1.0730	0.6018	0.103*
C21	0.4459 (2)	0.9222 (4)	0.66824 (17)	0.0938 (9)
H21	0.4489	0.9654	0.7233	0.113*
C22	0.48819 (18)	0.7960 (4)	0.66036 (17)	0.0896 (8)
H22	0.5203	0.7537	0.7099	0.108*
C23	0.48383 (15)	0.7297 (3)	0.57906 (15)	0.0736 (6)
H23	0.5123	0.6426	0.5739	0.088*
N1	0.17660 (9)	0.73225 (14)	0.29437 (9)	0.0405 (3)
O1	0.01013 (8)	0.74327 (13)	0.24414 (9)	0.0550 (3)
O2	0.11545 (9)	0.90024 (12)	0.17575 (8)	0.0561 (3)
O3	0.27314 (8)	1.02147 (12)	0.28681 (8)	0.0544 (3)
O4	0.32709 (11)	1.14258 (15)	0.17888 (9)	0.0712 (4)
S1	0.09482 (3)	0.76585 (4)	0.21008 (3)	0.04212 (12)
S2	0.43695 (3)	0.71174 (6)	0.40011 (3)	0.05871 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0493 (9)	0.0344 (8)	0.0324 (8)	−0.0008 (7)	0.0050 (7)	−0.0040 (7)
C2	0.0514 (10)	0.0450 (9)	0.0421 (10)	−0.0070 (8)	0.0040 (8)	−0.0032 (8)
C3	0.0662 (12)	0.0463 (10)	0.0473 (11)	−0.0130 (9)	0.0105 (9)	0.0007 (8)
C4	0.0806 (13)	0.0408 (9)	0.0405 (10)	−0.0069 (9)	0.0033 (9)	0.0048 (8)
C5	0.0604 (11)	0.0417 (9)	0.0404 (9)	0.0018 (8)	−0.0027 (8)	−0.0027 (8)
C6	0.0519 (9)	0.0353 (8)	0.0355 (9)	0.0005 (7)	0.0036 (7)	−0.0066 (7)
C7	0.0454 (9)	0.0422 (9)	0.0397 (9)	−0.0008 (7)	0.0057 (7)	−0.0065 (7)
C8	0.0481 (9)	0.0408 (9)	0.0390 (9)	−0.0030 (7)	0.0105 (7)	−0.0067 (7)
C9	0.0580 (10)	0.0438 (9)	0.0487 (10)	−0.0043 (8)	0.0162 (8)	−0.0032 (8)
C10	0.0585 (11)	0.0451 (10)	0.0539 (12)	−0.0092 (8)	−0.0044 (9)	0.0015 (9)
C11	0.113 (2)	0.0501 (13)	0.102 (2)	0.0067 (12)	0.0184 (16)	−0.0035 (13)
C12	0.0707 (12)	0.0442 (10)	0.0436 (10)	−0.0074 (8)	0.0148 (9)	0.0013 (8)
C13	0.0913 (15)	0.0389 (10)	0.0581 (12)	−0.0086 (10)	0.0158 (11)	−0.0035 (9)
C14	0.0825 (14)	0.0500 (11)	0.0482 (11)	0.0101 (10)	0.0100 (10)	−0.0079 (9)
C15	0.0806 (13)	0.0579 (12)	0.0446 (11)	0.0002 (10)	0.0220 (10)	0.0007 (9)
C16	0.0657 (11)	0.0422 (9)	0.0455 (10)	−0.0056 (8)	0.0128 (9)	0.0043 (8)
C17	0.0436 (8)	0.0376 (8)	0.0354 (9)	0.0030 (7)	0.0015 (7)	0.0017 (7)
C18	0.0447 (10)	0.0705 (13)	0.0511 (11)	−0.0171 (9)	0.0025 (8)	−0.0018 (10)
C19	0.0653 (13)	0.0789 (15)	0.0596 (13)	−0.0093 (11)	0.0061 (10)	−0.0100 (11)
C20	0.0887 (17)	0.0921 (18)	0.0806 (18)	−0.0225 (14)	0.0230 (14)	−0.0285 (15)
C21	0.101 (2)	0.126 (3)	0.0559 (15)	−0.0570 (19)	0.0151 (14)	−0.0210 (17)
C22	0.0854 (18)	0.126 (2)	0.0537 (15)	−0.0416 (17)	−0.0083 (12)	0.0084 (16)
C23	0.0645 (13)	0.0873 (16)	0.0653 (15)	−0.0191 (11)	−0.0060 (11)	0.0076 (13)
N1	0.0465 (7)	0.0395 (7)	0.0350 (7)	−0.0020 (6)	0.0034 (6)	0.0009 (6)
O1	0.0473 (7)	0.0625 (8)	0.0560 (8)	0.0126 (6)	0.0097 (6)	−0.0015 (6)
O2	0.0733 (8)	0.0355 (6)	0.0579 (8)	0.0073 (6)	0.0010 (6)	0.0053 (6)
O3	0.0705 (8)	0.0421 (7)	0.0537 (7)	−0.0073 (6)	0.0205 (6)	−0.0047 (6)
O4	0.0962 (11)	0.0635 (9)	0.0545 (9)	−0.0183 (8)	0.0113 (8)	0.0085 (7)
S1	0.0477 (2)	0.0375 (2)	0.0408 (2)	0.00722 (17)	0.00382 (18)	0.00013 (17)
S2	0.0446 (3)	0.0741 (3)	0.0573 (3)	−0.0010 (2)	0.0058 (2)	−0.0084 (3)

Geometric parameters (Å, º) top

C1—C2	1.388 (2)	C12—C17	1.383 (2)
C1—C6	1.398 (2)	C12—H12	0.9300
C1—N1	1.422 (2)	C13—C14	1.371 (3)
C2—C3	1.377 (2)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.371 (3)
C3—C4	1.391 (3)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.381 (3)
C4—C5	1.369 (2)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.376 (2)
C5—C6	1.397 (2)	C16—H16	0.9300
C5—H5	0.9300	C17—S1	1.7532 (16)
C6—C7	1.440 (2)	C18—C19	1.371 (3)
C7—C8	1.353 (2)	C18—C23	1.382 (3)
C7—S2	1.7545 (17)	C18—S2	1.785 (2)
C8—N1	1.418 (2)	C19—C20	1.392 (3)
C8—C9	1.484 (2)	C19—H19	0.9300
C9—O3	1.451 (2)	C20—C21	1.373 (4)
C9—H9A	0.9700	C20—H20	0.9300
C9—H9B	0.9700	C21—C22	1.356 (4)
C10—O4	1.196 (2)	C21—H21	0.9300
C10—O3	1.337 (2)	C22—C23	1.383 (4)
C10—C11	1.488 (3)	C22—H22	0.9300
C11—H11A	0.9600	C23—H23	0.9300
C11—H11B	0.9600	N1—S1	1.6763 (14)
C11—H11C	0.9600	O1—S1	1.4190 (12)
C12—C13	1.371 (3)	O2—S1	1.4201 (12)

C2—C1—C6	121.60 (15)	C12—C13—H13	119.8
C2—C1—N1	131.17 (15)	C14—C13—H13	119.8
C6—C1—N1	107.21 (13)	C15—C14—C13	120.33 (18)
C3—C2—C1	117.01 (17)	C15—C14—H14	119.8
C3—C2—H2	121.5	C13—C14—H14	119.8
C1—C2—H2	121.5	C14—C15—C16	120.22 (17)
C2—C3—C4	122.14 (17)	C14—C15—H15	119.9
C2—C3—H3	118.9	C16—C15—H15	119.9
C4—C3—H3	118.9	C17—C16—C15	118.97 (16)
C5—C4—C3	120.78 (17)	C17—C16—H16	120.5
C5—C4—H4	119.6	C15—C16—H16	120.5
C3—C4—H4	119.6	C16—C17—C12	120.98 (15)
C4—C5—C6	118.46 (17)	C16—C17—S1	119.59 (13)
C4—C5—H5	120.8	C12—C17—S1	119.40 (12)
C6—C5—H5	120.8	C19—C18—C23	120.1 (2)
C5—C6—C1	120.00 (15)	C19—C18—S2	120.85 (16)
C5—C6—C7	132.54 (16)	C23—C18—S2	118.90 (18)
C1—C6—C7	107.41 (14)	C18—C19—C20	119.8 (2)
C8—C7—C6	108.92 (14)	C18—C19—H19	120.1
C8—C7—S2	126.09 (13)	C20—C19—H19	120.1
C6—C7—S2	124.99 (13)	C21—C20—C19	119.4 (3)
C7—C8—N1	108.51 (14)	C21—C20—H20	120.3
C7—C8—C9	127.31 (15)	C19—C20—H20	120.3
N1—C8—C9	123.79 (15)	C22—C21—C20	120.7 (3)
O3—C9—C8	106.62 (12)	C22—C21—H21	119.6
O3—C9—H9A	110.4	C20—C21—H21	119.6
C8—C9—H9A	110.4	C21—C22—C23	120.4 (3)
O3—C9—H9B	110.4	C21—C22—H22	119.8
C8—C9—H9B	110.4	C23—C22—H22	119.8
H9A—C9—H9B	108.6	C18—C23—C22	119.4 (3)
O4—C10—O3	123.03 (18)	C18—C23—H23	120.3
O4—C10—C11	126.05 (19)	C22—C23—H23	120.3
O3—C10—C11	110.92 (18)	C8—N1—C1	107.94 (13)
C10—C11—H11A	109.5	C8—N1—S1	126.33 (11)
C10—C11—H11B	109.5	C1—N1—S1	123.64 (11)
H11A—C11—H11B	109.5	C10—O3—C9	115.82 (13)
C10—C11—H11C	109.5	O1—S1—O2	120.31 (7)
H11A—C11—H11C	109.5	O1—S1—N1	105.42 (7)
H11B—C11—H11C	109.5	O2—S1—N1	106.70 (7)
C13—C12—C17	119.13 (16)	O1—S1—C17	109.01 (8)
C13—C12—H12	120.4	O2—S1—C17	109.15 (8)
C17—C12—H12	120.4	N1—S1—C17	105.16 (7)
C12—C13—C14	120.36 (17)	C7—S2—C18	100.69 (8)

C6—C1—C2—C3	0.8 (2)	C19—C20—C21—C22	−0.9 (4)
N1—C1—C2—C3	−177.37 (16)	C20—C21—C22—C23	−0.5 (4)
C1—C2—C3—C4	0.2 (3)	C19—C18—C23—C22	0.7 (3)
C2—C3—C4—C5	−0.6 (3)	S2—C18—C23—C22	176.63 (16)
C3—C4—C5—C6	−0.1 (3)	C21—C22—C23—C18	0.6 (3)
C4—C5—C6—C1	1.1 (2)	C7—C8—N1—C1	−1.09 (17)
C4—C5—C6—C7	178.16 (17)	C9—C8—N1—C1	−174.33 (14)
C2—C1—C6—C5	−1.5 (2)	C7—C8—N1—S1	−165.03 (11)
N1—C1—C6—C5	177.06 (14)	C9—C8—N1—S1	21.7 (2)
C2—C1—C6—C7	−179.21 (14)	C2—C1—N1—C8	179.43 (16)
N1—C1—C6—C7	−0.66 (16)	C6—C1—N1—C8	1.06 (16)
C5—C6—C7—C8	−177.32 (17)	C2—C1—N1—S1	−16.1 (2)
C1—C6—C7—C8	−0.01 (18)	C6—C1—N1—S1	165.54 (11)
C5—C6—C7—S2	2.9 (3)	O4—C10—O3—C9	−3.4 (3)
C1—C6—C7—S2	−179.79 (12)	C11—C10—O3—C9	177.29 (17)
C6—C7—C8—N1	0.68 (18)	C8—C9—O3—C10	−172.38 (15)
S2—C7—C8—N1	−179.54 (11)	C8—N1—S1—O1	−163.03 (13)
C6—C7—C8—C9	173.61 (15)	C1—N1—S1—O1	35.40 (14)
S2—C7—C8—C9	−6.6 (2)	C8—N1—S1—O2	−34.03 (15)
C7—C8—C9—O3	−100.22 (19)	C1—N1—S1—O2	164.40 (12)
N1—C8—C9—O3	71.71 (19)	C8—N1—S1—C17	81.83 (14)
C17—C12—C13—C14	−1.0 (3)	C1—N1—S1—C17	−79.75 (13)
C12—C13—C14—C15	0.6 (3)	C16—C17—S1—O1	143.04 (14)
C13—C14—C15—C16	0.2 (3)	C12—C17—S1—O1	−35.16 (16)
C14—C15—C16—C17	−0.6 (3)	C16—C17—S1—O2	9.83 (16)
C15—C16—C17—C12	0.2 (3)	C12—C17—S1—O2	−168.37 (14)
C15—C16—C17—S1	−177.98 (14)	C16—C17—S1—N1	−104.33 (14)
C13—C12—C17—C16	0.6 (3)	C12—C17—S1—N1	77.48 (15)
C13—C12—C17—S1	178.76 (15)	C8—C7—S2—C18	110.04 (16)
C23—C18—C19—C20	−2.1 (3)	C6—C7—S2—C18	−70.22 (16)
S2—C18—C19—C20	−177.95 (16)	C19—C18—S2—C7	−58.87 (17)
C18—C19—C20—C21	2.2 (3)	C23—C18—S2—C7	125.22 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N1/C1/C6–C8 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O4ⁱ	0.93	2.59	3.274 (2)	131
C15—H15···Cg1ⁱⁱ	0.93	2.77	3.559 (2)	143
C16—H16···Cg2ⁱⁱ	0.93	2.72	3.5146 (19)	143

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+1/2, z−3/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₉NO₄S₂
M_r	437.51
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.6530 (6), 9.4482 (4), 15.2461 (7)
β (°)	97.055 (3)
V (Å³)	2094.76 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.25 × 0.22 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.981, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	19397, 5235, 3638
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.104, 1.03
No. of reflections	5235
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.29

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N1/C1/C6–C8 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O4ⁱ	0.93	2.59	3.274 (2)	130.5
C15—H15···Cg1ⁱⁱ	0.93	2.77	3.559 (2)	143
C16—H16···Cg2ⁱⁱ	0.93	2.72	3.5146 (19)	143

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+1/2, z−3/2.

Acknowledgements

EG and ASP thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for the X-ray intensity data collection.

References

Andreani, A., Granaiola, M., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Giorgi, G., Salvini, L. & Garaliene, V. (2001). Anticancer Drug Des. 16, 167–174. Web of Science PubMed CAS Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2004). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. 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
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Mukhopadhyay, S., Handy, G. A., Funayama, S. & Cordell, G. A. (1981). J. Nat. Prod. 44, 696–700. CrossRef CAS PubMed Web of Science Google Scholar
Quetin-Leclercq, J. (1994). J. Pharm. Belg. 49, 181–192. CAS PubMed Google Scholar
Ravishankar, T., Chinnakali, K., Arumugam, N., Srinivasan, P. C., Usman, A. & Fun, H.-K. (2005). Acta Cryst. E61, o2455–o2457. Web of Science CSD CrossRef IUCr Journals 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
Singh, U. P., Sarma, B. K., Mishra, P. K. & Ray, A. B. (2000). Folia Microbiol. (Praha), 45, 173–176. Web of Science CrossRef PubMed CAS Google Scholar
Sivaraman, J., Subramanian, K., Velmurugan, D., Subramanian, E. & Seetharaman, J. (1996). J. Mol. Struct. 385, 123–128. CSD CrossRef CAS Web of Science Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Taylor, D. L., Ahmed, P. S., Chambers, P., Tyms, A. S., Bedard, J., Duchaine, J., Falardeau, G., Lavallee, J. F., Brown, W., Rando, R. F. & Bowlin, T. (1999). Antivir. Chem. Chemother. 10, 79–86. Web of Science PubMed CAS Google Scholar
Williams, T. M., Ciccarone, T. M., MacTough, S. C., Rooney, C. S., Balani, S. K., Condra, J. H., Emini, E. A., Goldman, M. E., Greenlee, W. J. & Kauffman, L. R. (1993). J. Med. Chem. 36, 1291–1294. CrossRef CAS PubMed Web of Science Google Scholar

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Volume 67| Part 5| May 2011| Pages o1240-o1241

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