N-[(3-Phenylsulfanyl-1-phenylsulfonyl-1H-indol-2-yl)methyl]acetamide

Thenmozhi, S.; SubbiahPandi, A.; Dhayalan, V.; MohanaKrishnan, A.K.

doi:10.1107/S1600536809012525

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Pages o1020-o1021

doi:10.1107/S1600536809012525

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N-[(3-Phenylsulfanyl-1-phenylsulfonyl-1H-indol-2-yl)methyl]acetamide

S. Thenmozhi,^a A. SubbiahPandi,^a ^* V. Dhayalan ^b and A. K. MohanaKrishnan ^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_spandian@yahoo.com

(Received 30 March 2009; accepted 2 April 2009; online 10 April 2009)

In the title compound, C₂₃H₂₀N₂O₃S₂, the phenylsulfonyl ring and phenylthio ring make dihedral angles of 66.5 (7) and 81.2 (6)°, respectively, with the indole unit. In the crystal, molecules are linked into centrosymmetric dimers via pairs of N—H⋯O hydrogen bonds with graph-set motif R₂²(14). The crystal structure is further stabilized by weak intermolecular C—H⋯O and very weak C—H⋯π interactions.

Related literature

For the biological activity 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 a related structure, see: Ravishankar et al. (2005 ).

Experimental

Crystal data

C₂₃H₂₀N₂O₃S₂
M_r = 436.53
Triclinic, $[P \overline 1]$
a = 8.8129 (2) Å
b = 10.8880 (3) Å
c = 11.3711 (3) Å
α = 86.698 (1)°
β = 76.494 (1)°
γ = 83.317 (1)°
V = 1053.21 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 293 K
0.21 × 0.19 × 0.17 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.943, T_max = 0.953
28160 measured reflections
7167 independent reflections
5294 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.121
S = 0.98
7167 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.86	2.48	3.3179 (15)	165
C21—H21⋯O1ⁱⁱ	0.93	2.44	3.2666 (18)	149
C5—H5⋯Cg3ⁱⁱⁱ	0.93	2.94	3.7634 (18)	149
C9—H9A⋯Cg4^iv	0.97	2.95	3.5792 (16)	124
C11—H11A⋯Cg2^v	0.96	2.91	3.5974 (21)	129
C16—H16⋯Cg4^vi	0.93	2.95	3.7453 (21)	145
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) x, y, z-1; (iii) x-1, y, z; (iv) -x+2, -y+1, -z+1; (v) -x+1, -y+1, -z+2; (vi) -x+2, -y, -z+1. Cg2, Cg3 and Cg4 are the centroids of the C1–C6, C12–C17 and C18–C23 rings, respectively.

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: 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/S1600536809012525/bt2922sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809012525/bt2922Isup2.hkl

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 (Fig. 1) have been carried out.

The mean plane of the indole ring system makes dihedral angles of 66.5 (7) and 81.2 (6)° with respect to the phenyl rings. The S–O, S–C, and S–N distances are 1.419 (11), 1.750 (13) and 1.679 (11) 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 (9) Å] and N1–C8 [1.433 (6) Å], are longer than the mean value of 1.355 (14)Å for N atoms with planar configurations.

Via N2–H2···O2 hydrogen bonds the molecules form cyclic centrosymmetric dimers [R₂²(14)] shown in Fig.2. The structure is further stabilized by intermolecular C–H···π and C–H···O interactions as shown in Table. 1.

Related literature top

For the biological activity 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 a related structure, see: Ravishankar et al. (2005). Cg2, Cg3 and Cg4 are the centroids of the C1–C6, C12–C17 and C18–C23 rings, respectively.

Experimental top

To a solution of 1-phenylsulfonyl-2-(bromomethyl)-3-(phenylthio)-1H-indole (0.5 g, 1.09 mmol) in dry acetonitrile (20 ml), ZnBr₂ (0.49 g, 2.18 mmol), was added. The reaction mixture was then refluxed for 5 hr under N₂ atmosphere. It was then poured over ice-water (30 ml) containing 1 ml of conc.HCl, extracted with CHCl₃ (30 ml) and dried (Na₂ SO₄). Removal of solvent followed by crystallization from methanol afforded amide product. The amide was recrystallization from CDCl₃. 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: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELX97 (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 crystal structure showing the centrosymmetric hydrogen bond motif R₂²(14). For the sake of clarity, the H atoms not involved in the motif have been omitted. The atoms marked with an asterisk (*) are at the symmetry position (-x, 1 - y, 2 - z). The dashed lines indicate the hydrogen bonds.

N-[(3-Phenylsulfanyl-1-phenylsulfonyl-1H-indol-2- yl)methyl]acetamide top

Crystal data top

C₂₃H₂₀N₂O₃S₂	Z = 2
M_r = 436.53	F(000) = 456
Triclinic, P1	D_x = 1.377 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8129 (2) Å	Cell parameters from 7167 reflections
b = 10.8880 (3) Å	θ = 2.4–31.9°
c = 11.3711 (3) Å	µ = 0.28 mm⁻¹
α = 86.698 (1)°	T = 293 K
β = 76.494 (1)°	Block, colourless
γ = 83.317 (1)°	0.21 × 0.19 × 0.17 mm
V = 1053.21 (5) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	7167 independent reflections
Radiation source: fine-focus sealed tube	5294 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 31.9°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.943, T_max = 0.953	k = −16→16
28160 measured reflections	l = −16→16

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0595P)² + 0.2774P] where P = (F_o² + 2F_c²)/3
7167 reflections	(Δ/σ)_max = 0.005
272 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₂₃H₂₀N₂O₃S₂	γ = 83.317 (1)°
M_r = 436.53	V = 1053.21 (5) Å³
Triclinic, P1	Z = 2
a = 8.8129 (2) Å	Mo Kα radiation
b = 10.8880 (3) Å	µ = 0.28 mm⁻¹
c = 11.3711 (3) Å	T = 293 K
α = 86.698 (1)°	0.21 × 0.19 × 0.17 mm
β = 76.494 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	7167 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5294 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.953	R_int = 0.026
28160 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 0.98	Δρ_max = 0.33 e Å⁻³
7167 reflections	Δρ_min = −0.39 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	0.80217 (15)	0.18662 (12)	0.83970 (11)	0.0347 (3)
C2	0.79544 (18)	0.07935 (15)	0.91125 (14)	0.0470 (3)
H2	0.8532	0.0644	0.9703	0.056*
C3	0.6993 (2)	−0.00414 (16)	0.89092 (17)	0.0567 (4)
H3	0.6929	−0.0775	0.9370	0.068*
C4	0.6116 (2)	0.01768 (16)	0.80390 (17)	0.0561 (4)
H4	0.5467	−0.0404	0.7937	0.067*
C5	0.61930 (18)	0.12411 (15)	0.73246 (14)	0.0465 (3)
H5	0.5611	0.1385	0.6736	0.056*
C6	0.71616 (15)	0.20927 (12)	0.75069 (11)	0.0348 (3)
C7	0.74318 (15)	0.33121 (12)	0.69884 (11)	0.0338 (3)
C8	0.83792 (15)	0.38163 (12)	0.75660 (11)	0.0329 (2)
C9	0.87341 (16)	0.51288 (13)	0.75136 (13)	0.0393 (3)
H9A	0.9854	0.5152	0.7415	0.047*
H9B	0.8427	0.5560	0.6822	0.047*
C10	0.64041 (17)	0.62259 (15)	0.87510 (15)	0.0463 (3)
C11	0.5609 (2)	0.66919 (19)	0.99829 (18)	0.0619 (5)
H11A	0.4948	0.7443	0.9901	0.093*
H11B	0.6387	0.6850	1.0405	0.093*
H11C	0.4982	0.6081	1.0430	0.093*
C12	1.17375 (14)	0.22315 (13)	0.72453 (12)	0.0355 (3)
C13	1.23409 (17)	0.30613 (15)	0.63391 (14)	0.0458 (3)
H13	1.2222	0.3904	0.6477	0.055*
C14	1.31247 (19)	0.26126 (19)	0.52229 (16)	0.0560 (4)
H14	1.3537	0.3157	0.4601	0.067*
C15	1.3295 (2)	0.1370 (2)	0.50313 (16)	0.0602 (5)
H15	1.3821	0.1075	0.4277	0.072*
C16	1.2700 (2)	0.05551 (18)	0.59387 (19)	0.0656 (5)
H16	1.2830	−0.0288	0.5798	0.079*
C17	1.19143 (19)	0.09758 (15)	0.70519 (16)	0.0517 (4)
H17	1.1506	0.0425	0.7669	0.062*
C18	0.76928 (15)	0.32193 (12)	0.45609 (11)	0.0336 (3)
C19	0.90885 (16)	0.24822 (14)	0.45385 (12)	0.0417 (3)
H19	0.9484	0.2367	0.5232	0.050*
C20	0.98919 (19)	0.19193 (16)	0.34812 (14)	0.0503 (4)
H20	1.0825	0.1418	0.3468	0.060*
C21	0.9327 (2)	0.20926 (16)	0.24488 (14)	0.0512 (4)
H21	0.9882	0.1719	0.1738	0.061*
C22	0.7938 (2)	0.28199 (17)	0.24709 (13)	0.0524 (4)
H22	0.7551	0.2934	0.1774	0.063*
C23	0.71127 (17)	0.33808 (15)	0.35210 (13)	0.0440 (3)
H23	0.6169	0.3867	0.3533	0.053*
N1	0.87779 (12)	0.29375 (10)	0.84621 (9)	0.0346 (2)
N2	0.78974 (13)	0.57402 (11)	0.86117 (11)	0.0403 (3)
H2A	0.8371	0.5792	0.9185	0.048*
O1	1.06998 (14)	0.18125 (12)	0.95384 (10)	0.0559 (3)
O2	1.09978 (14)	0.39630 (11)	0.88318 (11)	0.0552 (3)
O3	0.57273 (17)	0.62503 (18)	0.79379 (14)	0.0910 (5)
S1	1.06294 (4)	0.27656 (3)	0.86411 (3)	0.03906 (10)
S2	0.65950 (4)	0.40353 (3)	0.58434 (3)	0.04266 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0339 (6)	0.0363 (7)	0.0294 (6)	0.0033 (5)	−0.0017 (5)	−0.0011 (5)
C2	0.0472 (8)	0.0473 (8)	0.0409 (8)	0.0023 (6)	−0.0049 (6)	0.0087 (6)
C3	0.0589 (10)	0.0442 (9)	0.0590 (10)	−0.0056 (7)	−0.0003 (8)	0.0117 (7)
C4	0.0557 (9)	0.0456 (9)	0.0646 (11)	−0.0137 (7)	−0.0041 (8)	−0.0036 (8)
C5	0.0465 (8)	0.0474 (8)	0.0459 (8)	−0.0054 (6)	−0.0093 (6)	−0.0084 (6)
C6	0.0363 (6)	0.0365 (7)	0.0288 (6)	0.0022 (5)	−0.0039 (5)	−0.0048 (5)
C7	0.0373 (6)	0.0350 (6)	0.0270 (5)	0.0056 (5)	−0.0072 (5)	−0.0034 (5)
C8	0.0341 (6)	0.0346 (6)	0.0268 (5)	0.0043 (5)	−0.0043 (4)	−0.0025 (5)
C9	0.0388 (6)	0.0359 (7)	0.0403 (7)	−0.0002 (5)	−0.0049 (5)	−0.0030 (5)
C10	0.0393 (7)	0.0476 (8)	0.0508 (8)	0.0029 (6)	−0.0097 (6)	−0.0097 (7)
C11	0.0522 (9)	0.0638 (11)	0.0635 (11)	0.0005 (8)	0.0013 (8)	−0.0246 (9)
C12	0.0307 (6)	0.0404 (7)	0.0362 (6)	−0.0001 (5)	−0.0105 (5)	−0.0041 (5)
C13	0.0396 (7)	0.0441 (8)	0.0503 (8)	−0.0011 (6)	−0.0060 (6)	0.0022 (6)
C14	0.0432 (8)	0.0730 (12)	0.0446 (8)	−0.0027 (7)	0.0002 (6)	0.0076 (8)
C15	0.0448 (8)	0.0834 (14)	0.0490 (9)	−0.0026 (8)	−0.0006 (7)	−0.0234 (9)
C16	0.0572 (10)	0.0559 (11)	0.0783 (13)	−0.0077 (8)	0.0028 (9)	−0.0295 (10)
C17	0.0490 (8)	0.0422 (8)	0.0576 (9)	−0.0052 (6)	0.0015 (7)	−0.0055 (7)
C18	0.0365 (6)	0.0355 (6)	0.0295 (6)	−0.0043 (5)	−0.0093 (5)	0.0010 (5)
C19	0.0411 (7)	0.0508 (8)	0.0330 (6)	0.0029 (6)	−0.0113 (5)	−0.0029 (6)
C20	0.0460 (8)	0.0584 (10)	0.0411 (8)	0.0068 (7)	−0.0043 (6)	−0.0064 (7)
C21	0.0606 (9)	0.0569 (10)	0.0322 (7)	−0.0065 (7)	−0.0015 (6)	−0.0070 (6)
C22	0.0645 (10)	0.0649 (10)	0.0310 (7)	−0.0076 (8)	−0.0170 (7)	−0.0010 (7)
C23	0.0449 (7)	0.0534 (9)	0.0355 (7)	−0.0003 (6)	−0.0163 (6)	0.0022 (6)
N1	0.0343 (5)	0.0400 (6)	0.0282 (5)	0.0025 (4)	−0.0076 (4)	−0.0017 (4)
N2	0.0391 (6)	0.0397 (6)	0.0439 (6)	0.0019 (5)	−0.0137 (5)	−0.0120 (5)
O1	0.0594 (7)	0.0743 (8)	0.0344 (5)	0.0054 (6)	−0.0204 (5)	0.0089 (5)
O2	0.0576 (6)	0.0579 (7)	0.0580 (7)	−0.0021 (5)	−0.0261 (5)	−0.0220 (5)
O3	0.0563 (8)	0.1470 (15)	0.0704 (9)	0.0362 (9)	−0.0318 (7)	−0.0335 (9)
S1	0.04034 (17)	0.0485 (2)	0.03049 (16)	0.00304 (14)	−0.01514 (13)	−0.00580 (13)
S2	0.04688 (19)	0.0454 (2)	0.03417 (17)	0.01400 (14)	−0.01465 (14)	−0.00459 (14)

Geometric parameters (Å, º) top

C1—C2	1.3834 (19)	C12—S1	1.7496 (13)
C1—C6	1.3949 (18)	C13—C14	1.382 (2)
C1—N1	1.4226 (18)	C13—H13	0.9300
C2—C3	1.376 (2)	C14—C15	1.368 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.385 (3)	C15—C16	1.370 (3)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.375 (2)	C16—C17	1.369 (2)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.386 (2)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.3840 (18)
C6—C7	1.4439 (19)	C18—C23	1.3885 (17)
C7—C8	1.3543 (18)	C18—S2	1.7727 (13)
C7—S2	1.7477 (12)	C19—C20	1.382 (2)
C8—N1	1.4332 (16)	C19—H19	0.9300
C8—C9	1.4930 (19)	C20—C21	1.374 (2)
C9—N2	1.4482 (17)	C20—H20	0.9300
C9—H9A	0.9700	C21—C22	1.375 (2)
C9—H9B	0.9700	C21—H21	0.9300
C10—O3	1.2093 (19)	C22—C23	1.379 (2)
C10—N2	1.3368 (18)	C22—H22	0.9300
C10—C11	1.500 (2)	C23—H23	0.9300
C11—H11A	0.9600	N1—S1	1.6789 (11)
C11—H11B	0.9600	N2—H2A	0.8600
C11—H11C	0.9600	O1—S1	1.4193 (11)
C12—C13	1.382 (2)	O2—S1	1.4198 (12)
C12—C17	1.382 (2)

C2—C1—C6	121.75 (14)	C14—C13—H13	120.7
C2—C1—N1	130.00 (13)	C15—C14—C13	120.14 (16)
C6—C1—N1	108.02 (11)	C15—C14—H14	119.9
C3—C2—C1	116.88 (15)	C13—C14—H14	119.9
C3—C2—H2	121.6	C14—C15—C16	120.71 (16)
C1—C2—H2	121.6	C14—C15—H15	119.6
C2—C3—C4	122.07 (15)	C16—C15—H15	119.6
C2—C3—H3	119.0	C17—C16—C15	120.32 (17)
C4—C3—H3	119.0	C17—C16—H16	119.8
C5—C4—C3	120.89 (16)	C15—C16—H16	119.8
C5—C4—H4	119.6	C16—C17—C12	119.01 (16)
C3—C4—H4	119.6	C16—C17—H17	120.5
C4—C5—C6	118.11 (15)	C12—C17—H17	120.5
C4—C5—H5	120.9	C19—C18—C23	119.60 (13)
C6—C5—H5	120.9	C19—C18—S2	123.85 (10)
C5—C6—C1	120.29 (13)	C23—C18—S2	116.52 (10)
C5—C6—C7	132.35 (13)	C20—C19—C18	119.66 (13)
C1—C6—C7	107.20 (12)	C20—C19—H19	120.2
C8—C7—C6	109.04 (11)	C18—C19—H19	120.2
C8—C7—S2	125.89 (11)	C21—C20—C19	120.68 (15)
C6—C7—S2	125.02 (10)	C21—C20—H20	119.7
C7—C8—N1	108.48 (11)	C19—C20—H20	119.7
C7—C8—C9	128.32 (12)	C20—C21—C22	119.72 (14)
N1—C8—C9	122.13 (11)	C20—C21—H21	120.1
N2—C9—C8	110.29 (11)	C22—C21—H21	120.1
N2—C9—H9A	109.6	C21—C22—C23	120.40 (14)
C8—C9—H9A	109.6	C21—C22—H22	119.8
N2—C9—H9B	109.6	C23—C22—H22	119.8
C8—C9—H9B	109.6	C22—C23—C18	119.92 (13)
H9A—C9—H9B	108.1	C22—C23—H23	120.0
O3—C10—N2	121.55 (15)	C18—C23—H23	120.0
O3—C10—C11	122.30 (15)	C1—N1—C8	107.23 (10)
N2—C10—C11	116.11 (14)	C1—N1—S1	119.17 (9)
C10—C11—H11A	109.5	C8—N1—S1	118.64 (9)
C10—C11—H11B	109.5	C10—N2—C9	121.31 (12)
H11A—C11—H11B	109.5	C10—N2—H2A	119.3
C10—C11—H11C	109.5	C9—N2—H2A	119.3
H11A—C11—H11C	109.5	O1—S1—O2	119.66 (7)
H11B—C11—H11C	109.5	O1—S1—N1	106.41 (7)
C13—C12—C17	121.18 (14)	O2—S1—N1	106.61 (6)
C13—C12—S1	120.19 (11)	O1—S1—C12	108.97 (7)
C17—C12—S1	118.52 (12)	O2—S1—C12	110.17 (7)
C12—C13—C14	118.64 (15)	N1—S1—C12	103.77 (6)
C12—C13—H13	120.7	C7—S2—C18	101.32 (6)

C6—C1—C2—C3	−0.2 (2)	C19—C20—C21—C22	−0.9 (3)
N1—C1—C2—C3	173.51 (14)	C20—C21—C22—C23	0.3 (3)
C1—C2—C3—C4	−0.6 (2)	C21—C22—C23—C18	0.5 (2)
C2—C3—C4—C5	1.0 (3)	C19—C18—C23—C22	−0.8 (2)
C3—C4—C5—C6	−0.5 (2)	S2—C18—C23—C22	177.16 (12)
C4—C5—C6—C1	−0.3 (2)	C2—C1—N1—C8	−175.59 (13)
C4—C5—C6—C7	−175.17 (14)	C6—C1—N1—C8	−1.19 (13)
C2—C1—C6—C5	0.7 (2)	C2—C1—N1—S1	46.01 (18)
N1—C1—C6—C5	−174.30 (12)	C6—C1—N1—S1	−139.59 (9)
C2—C1—C6—C7	176.72 (12)	C7—C8—N1—C1	0.11 (13)
N1—C1—C6—C7	1.76 (14)	C9—C8—N1—C1	169.22 (11)
C5—C6—C7—C8	173.66 (14)	C7—C8—N1—S1	138.76 (10)
C1—C6—C7—C8	−1.72 (14)	C9—C8—N1—S1	−52.12 (14)
C5—C6—C7—S2	−3.8 (2)	O3—C10—N2—C9	−5.2 (3)
C1—C6—C7—S2	−179.22 (9)	C11—C10—N2—C9	172.65 (14)
C6—C7—C8—N1	0.98 (14)	C8—C9—N2—C10	−83.42 (16)
S2—C7—C8—N1	178.45 (9)	C1—N1—S1—O1	−43.85 (11)
C6—C7—C8—C9	−167.25 (12)	C8—N1—S1—O1	−177.59 (10)
S2—C7—C8—C9	10.2 (2)	C1—N1—S1—O2	−172.62 (10)
C7—C8—C9—N2	104.47 (15)	C8—N1—S1—O2	53.64 (11)
N1—C8—C9—N2	−62.33 (15)	C1—N1—S1—C12	71.05 (10)
C17—C12—C13—C14	0.4 (2)	C8—N1—S1—C12	−62.69 (11)
S1—C12—C13—C14	−175.91 (12)	C13—C12—S1—O1	−156.18 (11)
C12—C13—C14—C15	−0.2 (2)	C17—C12—S1—O1	27.46 (13)
C13—C14—C15—C16	−0.2 (3)	C13—C12—S1—O2	−23.05 (13)
C14—C15—C16—C17	0.4 (3)	C17—C12—S1—O2	160.59 (12)
C15—C16—C17—C12	−0.2 (3)	C13—C12—S1—N1	90.75 (12)
C13—C12—C17—C16	−0.2 (2)	C17—C12—S1—N1	−85.61 (12)
S1—C12—C17—C16	176.18 (14)	C8—C7—S2—C18	108.39 (12)
C23—C18—C19—C20	0.2 (2)	C6—C7—S2—C18	−74.53 (12)
S2—C18—C19—C20	−177.54 (12)	C19—C18—S2—C7	−15.37 (14)
C18—C19—C20—C21	0.6 (2)	C23—C18—S2—C7	166.79 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	2.48	3.3179 (15)	165
C21—H21···O1ⁱⁱ	0.93	2.44	3.2666 (18)	149
C5—H5···Cg3ⁱⁱⁱ	0.93	2.94	3.7634 (18)	149
C9—H9A···Cg4^iv	0.97	2.95	3.5792 (16)	124
C11—H11A···Cg2^v	0.96	2.91	3.597 (2)	129
C16—H16···Cg4^vi	0.93	2.95	3.745 (2)	145

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) x, y, z−1; (iii) x−1, y, z; (iv) −x+2, −y+1, −z+1; (v) −x+1, −y+1, −z+2; (vi) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₀N₂O₃S₂
M_r	436.53
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.8129 (2), 10.8880 (3), 11.3711 (3)
α, β, γ (°)	86.698 (1), 76.494 (1), 83.317 (1)
V (Å³)	1053.21 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.21 × 0.19 × 0.17

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.943, 0.953
No. of measured, independent and observed [I > 2σ(I)] reflections	28160, 7167, 5294
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.743

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.121, 0.98
No. of reflections	7167
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.39

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELX97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	2.48	3.3179 (15)	165
C21—H21···O1ⁱⁱ	0.93	2.44	3.2666 (18)	149
C5—H5···Cg3ⁱⁱⁱ	0.93	2.94	3.7634 (18)	149
C9—H9A···Cg4^iv	0.97	2.95	3.5792 (16)	124
C11—H11A···Cg2^v	0.96	2.91	3.5974 (21)	129
C16—H16···Cg4^vi	0.93	2.95	3.7453 (21)	145

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) x, y, z−1; (iii) x−1, y, z; (iv) −x+2, −y+1, −z+1; (v) −x+1, −y+1, −z+2; (vi) −x+2, −y, −z+1.

Acknowledgements

ST and ASP thank Dr J. Jothi Kumar, Principal of Presidency College (Autonomous), Chennai, for providing computer and internet facilities. Dr Babu Vargheese, SAIF, IIT, Madras, India, is thanked for his help with the 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
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. 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 Gottingen, 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. 45, 173–176. Web of Science CrossRef 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). Antiviral Chem. Chemother. 10, 79–86. 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