9-Meth­oxy-5-phenyl­sulfonyl-5H-benzo[b]carbazole

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

doi:10.1107/S1600536808024756

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 9| September 2008| Pages o1712-o1713

doi:10.1107/S1600536808024756

Open

access

9-Methoxy-5-phenylsulfonyl-5H-benzo[b]carbazole

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

^aDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and ^cDepartment of Physics, Presidency College, Chennai 600 005, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com

(Received 30 July 2008; accepted 1 August 2008; online 6 August 2008)

In the title compound, C₂₃H₁₇NO₃S, the mean plane of the benzo[b]carbazole ring system makes a dihedral angle of 77.17 (4)° with the phenyl ring. The S atom is in a distorted tetrahedral configuration. There are three intramolecular C—H⋯O interactions forming five- and six-membered rings with graph-set motifs S(5) and S(6), respectively.

Related literature

For related literature, see: Allen et al. (1987 ); Chakkaravarthi et al. (2007 , 2008 ); Diaz et al. (2002 ); Etter et al. (1990 ); Govindasamy et al. (1998 ); Hökelek et al. (1998 ); Hosomi et al. (2000 ); Itoigawa et al. (2000 ); Ramsewak et al. (1999 ); Rodriguez et al. (1995 ); Sankaranarayanan et al. (2000 ); Tachibana et al. (2001 ); Zhang et al. (2004 ).

Experimental

Crystal data

C₂₃H₁₇NO₃S
M_r = 387.44
Triclinic, $[P \overline 1]$
a = 8.3608 (3) Å
b = 9.3103 (3) Å
c = 12.1754 (4) Å
α = 76.061 (2)°
β = 88.680 (1)°
γ = 88.715 (2)°
V = 919.46 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 295 (2) K
0.30 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEX2 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.909, T_max = 0.969
23200 measured reflections
5739 independent reflections
4330 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.134
S = 1.05
5739 reflections
254 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
C8—H8⋯O1	0.93	2.36	2.951 (2)	121
C21—H21⋯O2	0.93	2.36	2.9460 (18)	121
C6—H6⋯O1	0.93	2.54	2.906 (2)	104

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808024756/bt2761sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808024756/bt2761Isup2.hkl

checkCIF report

Comment top

Carbazole derivatives exhibit antitumor (Itoigawa et al., 2000), antioxidative (Tachibana et al., 2001), anti-inflammatory and antimutagenic (Ramsewak et al., 1999) activities. These compounds are thermally and photochemically stable, which makes them useful materials for technological applications. For instance, the carbazole ring is easily funtionalized and covalently linked to other molecules (Diaz et al., 2002). This enables its use as a convenient building block for the design and synthesis of molecular glasses, which are widely studied as components of electroactive and photoactive materials (Zhang et al., 2004).

The geometric parameters in (I), (Fig. 1) agree with the reported similiar structures (Hökelek et al., 1998; Hosomi et al., 2000). The mean planes of the benzo[b]carbazole and phenyl ring form a dihedral angle of 77.17 (4)°. The N1—S1—C1 plane is almost orthogonal to carbazole ring [dihedral angle 89.54 (5)°] and phenyl ring [dihedral angle 86.02 (6)°]. The best plane of pyrrole ring N1/C7/C12/C13/C22 subtends a dihedral angle of 30.13 (8)° with sulfonyl group.

The average S—O, S—C, and S—N distances are comparable with those observed in similiar structures (Chakkaravarthi et al., 2007; Sankaranarayanan et al., 2000). The N—C bond lengths, namely N1—C7 and N1—C22 [1.4352 (17) & 1.4340 (16) Å] deviate slightly from the normal mean value reported in the literature (Allen et al., 1987). This indicates that the substitution of the phenylsulfonyl group at atom N1 results in lengthening of the C—N bond lengths. This may be due to the electron-withdrawing character of the phenylsulfonyl group (Govindasamy et al., 1998).

The S atom exhibits significant deviation from a regular tetrahedron, with the largest deviations being seen for the O1—S1—O2 [120.09 (9)°] and O1—S1—N1 [106.78 (7)°] angles. 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; Rodriguez et al., 1995). The sum of the bond angles around N1 [351.97°] indicate the sp² hybridized state of the atom N, in the molecule.

The benzene ring C15—C20 is almost coplanar with methoxy group [torsion angle C23—O3—C17—C16 5.4 (2)°]. The torsion angles O1—S1—N1—C7 and O2—S1—N1—C22 [-44.62 (12)° and 41.56 (12)°, respectively] describe the syn conformation of the phenylsulfonyl group with respect to benzocarbazole ring system. This conformation is influenced by the intramolecular C—H··· O hydrogen bonds, C8—H8··· O1 and C21—H21···O2, involving sulfonyl atoms O1 and O2 (Table 1). The intramolecular hydrogen bonds form a six-membered ring with a graph-set motif of S(6) and a five-membered ring with a graph-set motif of S(5) (Etter et al., 1990).

Related literature top

For related literature, see: Allen et al. (1987); Chakkaravarthi et al. (2007, 2008); Diaz et al. (2002); Etter et al. (1990); Govindasamy et al. (1998); Hökelek et al. (1998); Hosomi et al. (2000); Itoigawa et al. (2000); Ramsewak et al. (1999); Rodriguez et al. (1995); Sankaranarayanan et al. (2000); Tachibana et al. (2001); Zhang et al. (2004).

Experimental top

To a solution of diethyl 2-((2-(bromomethyl)-1-(phenylsulfonyl)-1H-indol-3-yl)methylene) malonate (0.57 mmol) in dry 1,2-DCE (10 ml), ZnBr₂ (1.15 mmol) and anisole (1.15 mmol) were added. The reaction mixture was then refluxed for 1 h under N₂ atmosphere. It was then poured over ice-water (30 ml) containing 1 ml of concentrated HCl, extracted with Chloroform (2 X 10 ml) and dried (Na₂SO₄). The solvent was removed under vacuo, then crude products was purified by flash column chromatography (silica gel, 230–420 mesh, n-hexane/ethyl acetate 98:2) afforded the title compound suitable for X-ray analysis.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), with atom labeling scheme. Displacement ellipsoids are drawn at 50% probability level. H atoms are presented as a small spheres of arbitrary radius. Intramolecular H-bonds are shown as dashed lines.

9-Methoxy-5-phenylsulfonyl-5H-benzo[b]carbazole top

Crystal data top

C₂₃H₁₇NO₃S	Z = 2
M_r = 387.44	F(000) = 404
Triclinic, P1	D_x = 1.399 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3608 (3) Å	Cell parameters from 6534 reflections
b = 9.3103 (3) Å	θ = 2.4–30.7°
c = 12.1754 (4) Å	µ = 0.20 mm⁻¹
α = 76.061 (2)°	T = 295 K
β = 88.680 (1)°	Block, colourless
γ = 88.715 (2)°	0.30 × 0.20 × 0.16 mm
V = 919.46 (5) Å³

Data collection top

Bruker Kappa APEX2 diffractometer	5739 independent reflections
Radiation source: fine-focus sealed tube	4330 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω and ϕ scans	θ_max = 30.9°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.909, T_max = 0.969	k = −12→13
23200 measured reflections	l = −17→17

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0653P)² + 0.1785P] where P = (F_o² + 2F_c²)/3
5739 reflections	(Δ/σ)_max < 0.001
254 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₃H₁₇NO₃S	γ = 88.715 (2)°
M_r = 387.44	V = 919.46 (5) Å³
Triclinic, P1	Z = 2
a = 8.3608 (3) Å	Mo Kα radiation
b = 9.3103 (3) Å	µ = 0.20 mm⁻¹
c = 12.1754 (4) Å	T = 295 K
α = 76.061 (2)°	0.30 × 0.20 × 0.16 mm
β = 88.680 (1)°

Data collection top

Bruker Kappa APEX2 diffractometer	5739 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4330 reflections with I > 2σ(I)
T_min = 0.909, T_max = 0.969	R_int = 0.022
23200 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.05	Δρ_max = 0.29 e Å⁻³
5739 reflections	Δρ_min = −0.35 e Å⁻³
254 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.46793 (4)	0.47800 (4)	0.77672 (3)	0.04613 (11)
O1	0.54144 (15)	0.52427 (14)	0.66788 (10)	0.0629 (3)
O2	0.55193 (14)	0.49026 (13)	0.87398 (10)	0.0595 (3)
O3	0.19450 (16)	−0.22782 (14)	1.37354 (9)	0.0650 (3)
N1	0.42588 (14)	0.30123 (12)	0.79458 (9)	0.0434 (2)
C1	0.28152 (18)	0.56690 (14)	0.77467 (12)	0.0473 (3)
C2	0.2064 (2)	0.57404 (18)	0.87596 (15)	0.0616 (4)
H2	0.2572	0.5391	0.9447	0.074*
C3	0.0533 (3)	0.6349 (2)	0.8715 (2)	0.0820 (6)
H3	−0.0003	0.6411	0.9380	0.098*
C4	−0.0204 (3)	0.6865 (2)	0.7683 (3)	0.0895 (7)
H4	−0.1243	0.7246	0.7663	0.107*
C5	0.0581 (3)	0.6822 (2)	0.6692 (2)	0.0845 (7)
H5	0.0085	0.7199	0.6004	0.101*
C6	0.2093 (2)	0.62243 (18)	0.67116 (15)	0.0635 (4)
H6	0.2631	0.6191	0.6041	0.076*
C7	0.35493 (16)	0.24535 (15)	0.70734 (11)	0.0419 (3)
C8	0.37507 (19)	0.29073 (17)	0.59112 (12)	0.0512 (3)
H8	0.4363	0.3725	0.5579	0.061*
C9	0.3005 (2)	0.20949 (19)	0.52609 (13)	0.0578 (4)
H9	0.3115	0.2377	0.4477	0.069*
C10	0.2101 (2)	0.0875 (2)	0.57509 (13)	0.0602 (4)
H10	0.1620	0.0347	0.5294	0.072*
C11	0.1905 (2)	0.04329 (18)	0.69090 (13)	0.0540 (4)
H11	0.1295	−0.0388	0.7237	0.065*
C12	0.26309 (16)	0.12316 (15)	0.75771 (11)	0.0427 (3)
C13	0.27196 (15)	0.10092 (14)	0.87926 (11)	0.0409 (3)
C14	0.20944 (17)	−0.00631 (16)	0.96676 (12)	0.0457 (3)
H14	0.1427	−0.0777	0.9521	0.055*
C15	0.24777 (16)	−0.00676 (15)	1.07919 (11)	0.0428 (3)
C16	0.19098 (19)	−0.11947 (17)	1.17162 (12)	0.0504 (3)
H16	0.1228	−0.1911	1.1589	0.060*
C17	0.23668 (18)	−0.12252 (17)	1.27913 (12)	0.0498 (3)
C18	0.33749 (19)	−0.01305 (17)	1.29944 (12)	0.0516 (3)
H18	0.3674	−0.0160	1.3731	0.062*
C19	0.39146 (19)	0.09670 (16)	1.21281 (12)	0.0486 (3)
H19	0.4572	0.1686	1.2280	0.058*
C20	0.34939 (16)	0.10378 (14)	1.09928 (11)	0.0419 (3)
C21	0.41158 (17)	0.21431 (15)	1.00847 (12)	0.0444 (3)
H21	0.4774	0.2874	1.0216	0.053*
C22	0.37207 (15)	0.21053 (14)	0.90096 (11)	0.0398 (3)
C23	0.1076 (2)	−0.3496 (2)	1.35768 (15)	0.0671 (5)
H23A	0.0031	−0.3164	1.3303	0.101*
H23B	0.0974	−0.4218	1.4284	0.101*
H23C	0.1632	−0.3932	1.3036	0.101*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0454 (2)	0.04688 (19)	0.04625 (18)	−0.01263 (14)	0.00349 (13)	−0.01082 (13)
O1	0.0640 (7)	0.0674 (7)	0.0561 (6)	−0.0223 (6)	0.0174 (5)	−0.0124 (5)
O2	0.0592 (7)	0.0604 (6)	0.0604 (6)	−0.0184 (5)	−0.0094 (5)	−0.0151 (5)
O3	0.0758 (8)	0.0647 (7)	0.0478 (6)	−0.0110 (6)	−0.0011 (5)	0.0005 (5)
N1	0.0449 (6)	0.0423 (5)	0.0435 (5)	−0.0045 (5)	0.0008 (4)	−0.0115 (4)
C1	0.0536 (8)	0.0348 (6)	0.0532 (7)	−0.0069 (5)	0.0004 (6)	−0.0094 (5)
C2	0.0682 (10)	0.0485 (8)	0.0638 (9)	−0.0045 (7)	0.0141 (8)	−0.0062 (7)
C3	0.0766 (13)	0.0555 (10)	0.1082 (17)	0.0014 (9)	0.0332 (12)	−0.0121 (10)
C4	0.0642 (12)	0.0570 (11)	0.145 (2)	0.0128 (9)	−0.0064 (14)	−0.0210 (13)
C5	0.0874 (15)	0.0581 (11)	0.1115 (18)	0.0186 (10)	−0.0349 (14)	−0.0258 (11)
C6	0.0789 (12)	0.0500 (8)	0.0634 (9)	0.0034 (8)	−0.0149 (8)	−0.0160 (7)
C7	0.0396 (6)	0.0440 (6)	0.0445 (6)	0.0008 (5)	0.0015 (5)	−0.0154 (5)
C8	0.0554 (8)	0.0526 (8)	0.0460 (7)	−0.0061 (6)	0.0064 (6)	−0.0129 (6)
C9	0.0680 (10)	0.0649 (9)	0.0428 (7)	−0.0058 (8)	0.0028 (6)	−0.0177 (6)
C10	0.0701 (11)	0.0673 (10)	0.0492 (8)	−0.0115 (8)	−0.0030 (7)	−0.0243 (7)
C11	0.0595 (9)	0.0555 (8)	0.0503 (7)	−0.0133 (7)	0.0001 (6)	−0.0182 (6)
C12	0.0406 (7)	0.0464 (7)	0.0429 (6)	−0.0011 (5)	0.0010 (5)	−0.0146 (5)
C13	0.0369 (6)	0.0435 (6)	0.0434 (6)	0.0003 (5)	−0.0011 (5)	−0.0129 (5)
C14	0.0434 (7)	0.0473 (7)	0.0474 (7)	−0.0078 (5)	−0.0011 (5)	−0.0127 (5)
C15	0.0395 (6)	0.0437 (6)	0.0445 (6)	0.0013 (5)	−0.0003 (5)	−0.0098 (5)
C16	0.0492 (8)	0.0508 (7)	0.0490 (7)	−0.0055 (6)	0.0005 (6)	−0.0076 (6)
C17	0.0495 (8)	0.0499 (7)	0.0464 (7)	0.0041 (6)	0.0003 (6)	−0.0051 (6)
C18	0.0587 (9)	0.0516 (8)	0.0447 (7)	0.0086 (6)	−0.0078 (6)	−0.0121 (6)
C19	0.0534 (8)	0.0458 (7)	0.0486 (7)	0.0031 (6)	−0.0076 (6)	−0.0149 (6)
C20	0.0410 (7)	0.0411 (6)	0.0446 (6)	0.0053 (5)	−0.0027 (5)	−0.0126 (5)
C21	0.0455 (7)	0.0404 (6)	0.0490 (7)	−0.0019 (5)	−0.0039 (5)	−0.0133 (5)
C22	0.0373 (6)	0.0385 (6)	0.0438 (6)	0.0012 (5)	0.0000 (5)	−0.0107 (5)
C23	0.0704 (11)	0.0616 (10)	0.0617 (10)	−0.0096 (8)	0.0024 (8)	0.0004 (8)

Geometric parameters (Å, º) top

S1—O2	1.4197 (11)	C10—C11	1.377 (2)
S1—O1	1.4208 (11)	C10—H10	0.9300
S1—N1	1.6521 (12)	C11—C12	1.385 (2)
S1—C1	1.7461 (16)	C11—H11	0.9300
O3—C17	1.3641 (17)	C12—C13	1.4475 (18)
O3—C23	1.414 (2)	C13—C14	1.3748 (18)
N1—C22	1.4340 (16)	C13—C22	1.4107 (18)
N1—C7	1.4352 (17)	C14—C15	1.4120 (19)
C1—C2	1.386 (2)	C14—H14	0.9300
C1—C6	1.388 (2)	C15—C20	1.418 (2)
C2—C3	1.385 (3)	C15—C16	1.4219 (19)
C2—H2	0.9300	C16—C17	1.366 (2)
C3—C4	1.386 (3)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.407 (2)
C4—C5	1.369 (3)	C18—C19	1.356 (2)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.368 (3)	C19—C20	1.4200 (19)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—C21	1.4146 (19)
C7—C8	1.3833 (19)	C21—C22	1.3662 (18)
C7—C12	1.3933 (19)	C21—H21	0.9300
C8—C9	1.386 (2)	C23—H23A	0.9600
C8—H8	0.9300	C23—H23B	0.9600
C9—C10	1.381 (2)	C23—H23C	0.9600
C9—H9	0.9300

O2—S1—O1	119.66 (7)	C10—C11—H11	120.6
O2—S1—N1	106.69 (6)	C12—C11—H11	120.6
O1—S1—N1	106.78 (7)	C11—C12—C7	119.86 (13)
O2—S1—C1	109.52 (7)	C11—C12—C13	131.94 (13)
O1—S1—C1	108.60 (8)	C7—C12—C13	108.10 (12)
N1—S1—C1	104.52 (6)	C14—C13—C22	120.69 (12)
C17—O3—C23	117.30 (13)	C14—C13—C12	131.56 (13)
C22—N1—C7	107.12 (10)	C22—C13—C12	107.65 (11)
C22—N1—S1	122.77 (9)	C13—C14—C15	119.27 (13)
C7—N1—S1	122.08 (9)	C13—C14—H14	120.4
C2—C1—C6	121.82 (16)	C15—C14—H14	120.4
C2—C1—S1	119.46 (12)	C14—C15—C20	119.23 (12)
C6—C1—S1	118.64 (13)	C14—C15—C16	120.91 (13)
C3—C2—C1	117.85 (18)	C20—C15—C16	119.81 (13)
C3—C2—H2	121.1	C17—C16—C15	119.97 (14)
C1—C2—H2	121.1	C17—C16—H16	120.0
C2—C3—C4	120.2 (2)	C15—C16—H16	120.0
C2—C3—H3	119.9	O3—C17—C16	125.14 (15)
C4—C3—H3	119.9	O3—C17—C18	114.46 (13)
C5—C4—C3	120.8 (2)	C16—C17—C18	120.40 (14)
C5—C4—H4	119.6	C19—C18—C17	120.70 (14)
C3—C4—H4	119.6	C19—C18—H18	119.6
C6—C5—C4	120.1 (2)	C17—C18—H18	119.6
C6—C5—H5	119.9	C18—C19—C20	121.16 (14)
C4—C5—H5	119.9	C18—C19—H19	119.4
C5—C6—C1	119.11 (19)	C20—C19—H19	119.4
C5—C6—H6	120.4	C21—C20—C15	120.89 (12)
C1—C6—H6	120.4	C21—C20—C19	121.12 (13)
C8—C7—C12	121.66 (13)	C15—C20—C19	117.95 (13)
C8—C7—N1	129.40 (13)	C22—C21—C20	118.05 (13)
C12—C7—N1	108.81 (11)	C22—C21—H21	121.0
C7—C8—C9	117.38 (14)	C20—C21—H21	121.0
C7—C8—H8	121.3	C21—C22—C13	121.87 (12)
C9—C8—H8	121.3	C21—C22—N1	129.70 (12)
C10—C9—C8	121.48 (14)	C13—C22—N1	108.31 (11)
C10—C9—H9	119.3	O3—C23—H23A	109.5
C8—C9—H9	119.3	O3—C23—H23B	109.5
C11—C10—C9	120.74 (15)	H23A—C23—H23B	109.5
C11—C10—H10	119.6	O3—C23—H23C	109.5
C9—C10—H10	119.6	H23A—C23—H23C	109.5
C10—C11—C12	118.87 (14)	H23B—C23—H23C	109.5

O2—S1—N1—C22	41.56 (12)	C11—C12—C13—C14	−0.7 (3)
O1—S1—N1—C22	170.62 (11)	C7—C12—C13—C14	−176.98 (14)
C1—S1—N1—C22	−74.41 (12)	C11—C12—C13—C22	175.59 (15)
O2—S1—N1—C7	−173.68 (10)	C7—C12—C13—C22	−0.70 (15)
O1—S1—N1—C7	−44.62 (12)	C22—C13—C14—C15	−0.6 (2)
C1—S1—N1—C7	70.35 (11)	C12—C13—C14—C15	175.24 (13)
O2—S1—C1—C2	−29.51 (14)	C13—C14—C15—C20	0.2 (2)
O1—S1—C1—C2	−161.84 (12)	C13—C14—C15—C16	−177.31 (13)
N1—S1—C1—C2	84.48 (13)	C14—C15—C16—C17	176.37 (13)
O2—S1—C1—C6	153.51 (12)	C20—C15—C16—C17	−1.2 (2)
O1—S1—C1—C6	21.18 (14)	C23—O3—C17—C16	5.4 (2)
N1—S1—C1—C6	−92.51 (13)	C23—O3—C17—C18	−173.41 (14)
C6—C1—C2—C3	1.9 (2)	C15—C16—C17—O3	−177.59 (14)
S1—C1—C2—C3	−174.97 (13)	C15—C16—C17—C18	1.2 (2)
C1—C2—C3—C4	−0.1 (3)	O3—C17—C18—C19	178.60 (14)
C2—C3—C4—C5	−1.8 (3)	C16—C17—C18—C19	−0.3 (2)
C3—C4—C5—C6	1.9 (3)	C17—C18—C19—C20	−0.6 (2)
C4—C5—C6—C1	−0.1 (3)	C14—C15—C20—C21	0.4 (2)
C2—C1—C6—C5	−1.9 (3)	C16—C15—C20—C21	177.97 (12)
S1—C1—C6—C5	175.06 (14)	C14—C15—C20—C19	−177.30 (12)
C22—N1—C7—C8	−176.94 (14)	C16—C15—C20—C19	0.3 (2)
S1—N1—C7—C8	33.57 (19)	C18—C19—C20—C21	−177.08 (13)
C22—N1—C7—C12	−1.03 (14)	C18—C19—C20—C15	0.6 (2)
S1—N1—C7—C12	−150.52 (10)	C15—C20—C21—C22	−0.6 (2)
C12—C7—C8—C9	−0.2 (2)	C19—C20—C21—C22	177.01 (12)
N1—C7—C8—C9	175.27 (14)	C20—C21—C22—C13	0.2 (2)
C7—C8—C9—C10	−0.3 (3)	C20—C21—C22—N1	−175.36 (12)
C8—C9—C10—C11	0.4 (3)	C14—C13—C22—C21	0.4 (2)
C9—C10—C11—C12	−0.1 (3)	C12—C13—C22—C21	−176.35 (12)
C10—C11—C12—C7	−0.4 (2)	C14—C13—C22—N1	176.82 (12)
C10—C11—C12—C13	−176.35 (15)	C12—C13—C22—N1	0.06 (14)
C8—C7—C12—C11	0.5 (2)	C7—N1—C22—C21	176.62 (13)
N1—C7—C12—C11	−175.75 (13)	S1—N1—C22—C21	−34.15 (19)
C8—C7—C12—C13	177.36 (13)	C7—N1—C22—C13	0.58 (14)
N1—C7—C12—C13	1.07 (15)	S1—N1—C22—C13	149.81 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1	0.93	2.36	2.951 (2)	121
C21—H21···O2	0.93	2.36	2.9460 (18)	121
C6—H6···O1	0.93	2.54	2.906 (2)	104

Experimental details

Crystal data
Chemical formula	C₂₃H₁₇NO₃S
M_r	387.44
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.3608 (3), 9.3103 (3), 12.1754 (4)
α, β, γ (°)	76.061 (2), 88.680 (1), 88.715 (2)
V (Å³)	919.46 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.30 × 0.20 × 0.16

Data collection
Diffractometer	Bruker Kappa APEX2 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.909, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	23200, 5739, 4330
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.722

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.134, 1.05
No. of reflections	5739
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.35

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1	0.93	2.36	2.951 (2)	121
C21—H21···O2	0.93	2.36	2.9460 (18)	121
C6—H6···O1	0.93	2.54	2.906 (2)	104

Acknowledgements

The authors acknowledge the Sophisticated Analytical Instrument Facility, Indian Institute of Technology, Madras, for the data collection.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3673. 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
Diaz, J. L., Villacampa, B., Lopez-Calahorra, F. & Velasco, D. (2002). Chem. Mater. 14, 2240–2251. Web of Science CrossRef CAS Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Govindasamy, L., Velmurugan, D., Ravikumar, K. & Mohanakrishnan, A. K. (1998). Acta Cryst. C54, 277–279. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Hökelek, T., Gündüz, H., Patir, S. & Uludaug, N. (1998). Acta Cryst. C54, 1297–1299. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hosomi, H., Ohba, S. & Ito, Y. (2000). Acta Cryst. C56, e144–e146. CSD CrossRef CAS IUCr Journals Google Scholar
Itoigawa, M., Kashiwada, Y., Ito, C., Furukawa, H., Tachibana, Y., Bastow, K. F. & Lee, K. H. (2000). J. Nat. Prod. 63, 893–897. Web of Science CrossRef PubMed CAS Google Scholar
Ramsewak, R. S., Nair, M. G., Strasburg, G. M., DeWitt, D. L. & Nitiss, J. L. (1999). J. Agric. Food Chem. 47, 444–447. Web of Science CrossRef PubMed CAS Google Scholar
Rodriguez, J. G., del Valle, C., Esteban-Calderon, C. & Martinez-Repoll, M. (1995). J. Chem. Crystallogr. 25, 249–257. CSD CrossRef Web of Science Google Scholar
Sankaranarayanan, R., Velmurugan, D., Shanmuga Sundara Raj, S., Fun, H.-K., Babu, G. & Perumal, P. T. (2000). Acta Cryst. C56, 475–476. CrossRef CAS 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
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tachibana, Y., Kikuzaki, H., Lajis, N. H. & Nakatani, N. (2001). J. Agric. Food Chem. 49, 5589–5594. Web of Science CrossRef PubMed CAS Google Scholar
Zhang, Q., Chen, J., Cheng, Y., Wang, L., Ma, D., Jing, X. & Wang, F. (2004). J. Mater. Chem. 14, 895–900. Web of Science CrossRef CAS Google Scholar