8,9-Dimeth­oxy-5-phenyl­sulfonyl-5H-benzo[b]carbazole

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

doi:10.1107/S160053681001247X

organic compounds

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Volume 66| Part 5| May 2010| Page o1071

https://doi.org/10.1107/S160053681001247X

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8,9-Dimethoxy-5-phenylsulfonyl-5H-benzo[b]carbazole

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 600 025, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 12 March 2010; accepted 2 April 2010; online 14 April 2010)

In the title compound, C₂₄H₁₉NO₄S, the benzocarbazole ring system is planar (r.m.s. deviation = 0.016 Å) and forms a dihedral angle of 78.54 (4)° with the sulfonyl-bound phenyl ring. Intramolecular C—H⋯O interactions are observed. A C(8) chain running along the b axis is formed via intermolecular C—H⋯O hydrogen bonds. The chains are linked via weak C—H⋯ π interactions.

Related literature

For bond-length data, see: Allen et al. (1987 ). For the biological activity of carbazole derivatives, see: Itoigawa et al. (2000 ); Tachibana et al. (2001 ); Ramsewak et al. (1999 ). For related structures, see: Chakkaravarthi et al. (2008 ); Govindasamy et al. (1998 ).

Experimental

Crystal data

C₂₄H₁₉NO₄S
M_r = 417.46
Triclinic, $[P \overline 1]$
a = 7.8606 (2) Å
b = 9.5892 (2) Å
c = 13.8846 (4) Å
α = 100.387 (1)°
β = 93.168 (2)°
γ = 105.883 (1)°
V = 984.05 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.943, T_max = 0.962
26246 measured reflections
7025 independent reflections
5372 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.138
S = 1.04
7025 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1	0.93	2.34	2.9238 (19)	120
C6—H6⋯O2	0.93	2.37	2.9674 (15)	122
C2—H2⋯O2ⁱ	0.93	2.55	3.3361 (17)	143
C24—H24C⋯Cg1ⁱⁱ	0.96	2.84	3.727 (2)	154
C25—H25A⋯Cg2ⁱⁱⁱ	0.96	2.90	3.628 (2)	134
Symmetry codes: (i) x, y-1, z; (ii) -x+2, -y+1, -z; (iii) -x+2, -y, -z. Cg1 and Cg2 are the centroids of the C7–C10/C22/C23 and C1–C4/C21/C20 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 I, global. DOI: https://doi.org/10.1107/S160053681001247X/ci5059sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681001247X/ci5059Isup2.hkl

checkCIF report

Comment top

Carbazole and its derivatives are considered as potential compounds owing to their applications in pharmacy and molecular electronics. They also possess various biological activities such as antitumor (Itoigawa et al., 2000), antioxidative (Tachibana et al., 2001), anti-inflammatory and antimutagenic (Ramsewak et al., 1999) properties.

The benzocarbazole ring system is planar (r.m.s. deviation 0.016 Å) and it forms a dihedral angle of 78.54 (4)° with the sulfonyl-bound phenyl ring (Fig.1). The N—C bond lengths, namely N5—C19 and N5—C21 [1.432 (1) & 1.436 (2) Å] deviate slightly from the mean value reported in the literature (1.370 (12) Å; Allen et al., 1987). This may be due to the electron-withdrawing character of the phenylsulfonyl group (Govindasamy et al., 1998) substitued at N atom of the carbazole group. The S atom exhibits a distorted tetrahedral geometry. The widening of the O1—S1—O2 [119.60 (6)°] angle may be due to repulsive interactions between the two S═O bonds (Chakkaravarthi et al., 2008). The sum of the bond angles around N1 [350.6°] indicate the sp² hybridization. The methoxy groups substituted at C8 and C9 lie almost in the plane of the attached benzene ring [C7—C8—O3—C24 = -3.8 (2)° and C10—C9—O4—C25 = 6.8 (2)°].

The intermolecular C—H···O hydrogen bonds link the molecules into a C(8) chain running along the b axis (Fig.2). The packing of the molecules is further influenced by C—H··· π interactions.

Related literature top

For bond-length data, see: Allen et al. (1987). For the biological activity of carbazole derivatives, see: Itoigawa et al. (2000); Tachibana et al. (2001); Ramsewak et al. (1999). For related structures, see: Chakkaravarthi et al. (2008); Govindasamy et al. (1998).

Experimental top

To a solution of diethyl-2-[(2-bromomethyl-1-phenylsulfonyl-1H-indol-3-yl)methylene]malonate (0.41 g, 0.78 mmol) in dry 1,2-dichloroethane (15 ml), anhydrous ZnBr₂ (0.35 g, 1.55 mmol) and veratrole (0.12 ml, 0.94 mmol) were added. The mixture was refluxed for 5 h under N₂ atmosphere. The solvent was removed and the reaction mixture was quenched with ice-water (50 ml) containing 1 ml of conc. HCl, extracted with chloroform (2 × 10 ml) and dried (Na₂SO₄). Removal of the solvent followed by flash column chromatographic purification (n-hexane-ethyl acetate 99:1) led to the isolation of the title compound as a colourless solid. The compound was recrystallized from CDCl₃.

Structure description top

For bond-length data, see: Allen et al. (1987). For the biological activity of carbazole derivatives, see: Itoigawa et al. (2000); Tachibana et al. (2001); Ramsewak et al. (1999). For related structures, see: Chakkaravarthi et al. (2008); Govindasamy et al. (1998).

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, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
	Fig. 2. Crystal packing of the title compound. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

8,9-Dimethoxy-5-phenylsulfonyl-5H-benzo[b]carbazole top

Crystal data top

C₂₄H₁₉NO₄S	Z = 2
M_r = 417.46	F(000) = 436
Triclinic, P1	D_x = 1.409 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8606 (2) Å	Cell parameters from 7025 reflections
b = 9.5892 (2) Å	θ = 1.5–33.3°
c = 13.8846 (4) Å	µ = 0.20 mm⁻¹
α = 100.387 (1)°	T = 293 K
β = 93.168 (2)°	Block, colourless
γ = 105.883 (1)°	0.30 × 0.25 × 0.20 mm
V = 984.05 (4) Å³

Data collection top

Bruker Kappa APEXII area-detector diffractometer	7025 independent reflections
Radiation source: fine-focus sealed tube	5372 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω and φ scans	θ_max = 33.3°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −12→11
T_min = 0.943, T_max = 0.962	k = −14→13
26246 measured reflections	l = −21→21

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0749P)² + 0.1333P] where P = (F_o² + 2F_c²)/3
7025 reflections	(Δ/σ)_max = 0.001
273 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₄H₁₉NO₄S	γ = 105.883 (1)°
M_r = 417.46	V = 984.05 (4) Å³
Triclinic, P1	Z = 2
a = 7.8606 (2) Å	Mo Kα radiation
b = 9.5892 (2) Å	µ = 0.20 mm⁻¹
c = 13.8846 (4) Å	T = 293 K
α = 100.387 (1)°	0.30 × 0.25 × 0.20 mm
β = 93.168 (2)°

Data collection top

Bruker Kappa APEXII area-detector diffractometer	7025 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	5372 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.962	R_int = 0.024
26246 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.04	Δρ_max = 0.39 e Å⁻³
7025 reflections	Δρ_min = −0.25 e Å⁻³
273 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
S1	0.62768 (4)	0.24308 (3)	0.35159 (2)	0.03860 (9)
O1	0.54424 (14)	0.18104 (12)	0.42890 (8)	0.0543 (3)
O2	0.57390 (13)	0.35798 (11)	0.31820 (7)	0.0483 (2)
O3	0.84578 (17)	0.47850 (12)	−0.16011 (8)	0.0580 (3)
O4	0.89925 (15)	0.24214 (13)	−0.25315 (7)	0.0566 (3)
C1	0.6666 (2)	−0.24922 (15)	0.16579 (12)	0.0538 (3)
H1	0.7018	−0.2941	0.1083	0.065*
C2	0.6256 (2)	−0.32426 (16)	0.24138 (14)	0.0600 (4)
H2	0.6350	−0.4200	0.2351	0.072*
C3	0.5710 (2)	−0.25904 (16)	0.32592 (13)	0.0543 (4)
H3	0.5440	−0.3121	0.3757	0.065*
C4	0.55495 (18)	−0.11624 (15)	0.33915 (11)	0.0484 (3)
H4	0.5166	−0.0732	0.3962	0.058*
N5	0.59104 (14)	0.10465 (11)	0.25487 (8)	0.0387 (2)
C6	0.67353 (17)	0.25195 (13)	0.12110 (9)	0.0386 (2)
H6	0.6486	0.3362	0.1542	0.046*
C7	0.76027 (18)	0.37119 (14)	−0.01873 (9)	0.0421 (3)
H7	0.7390	0.4572	0.0142	0.051*
C8	0.81631 (18)	0.36643 (15)	−0.11016 (9)	0.0430 (3)
C9	0.84830 (17)	0.23465 (15)	−0.16184 (9)	0.0432 (3)
C10	0.82608 (18)	0.11485 (15)	−0.11883 (9)	0.0442 (3)
H10	0.8490	0.0300	−0.1525	0.053*
C11	0.74574 (18)	−0.00587 (13)	0.02134 (10)	0.0424 (3)
H11	0.7687	−0.0913	−0.0112	0.051*
C12	0.85883 (16)	0.30130 (14)	0.38223 (8)	0.0386 (2)
C13	0.9589 (2)	0.42875 (18)	0.35613 (11)	0.0530 (3)
H13	0.9045	0.4838	0.3228	0.064*
C14	1.1410 (2)	0.4730 (2)	0.38032 (12)	0.0677 (5)
H14	1.2102	0.5592	0.3641	0.081*
C15	1.2202 (2)	0.3895 (2)	0.42836 (13)	0.0687 (5)
H15	1.3429	0.4197	0.4445	0.082*
C16	1.1192 (3)	0.2617 (2)	0.45275 (15)	0.0726 (5)
H16	1.1743	0.2055	0.4845	0.087*
C17	0.9365 (2)	0.21628 (18)	0.43036 (12)	0.0575 (4)
H17	0.8674	0.1306	0.4473	0.069*
C18	0.68934 (16)	0.00057 (12)	0.11331 (9)	0.0379 (2)
C19	0.65257 (15)	0.12981 (12)	0.16256 (8)	0.0348 (2)
C20	0.65429 (16)	−0.10571 (13)	0.17721 (10)	0.0406 (2)
C21	0.59885 (15)	−0.04054 (13)	0.26328 (10)	0.0396 (2)
C22	0.76869 (16)	0.11715 (13)	−0.02368 (9)	0.0382 (2)
C23	0.73374 (16)	0.24697 (12)	0.02715 (8)	0.0368 (2)
C24	0.8057 (3)	0.60947 (18)	−0.11663 (13)	0.0630 (4)
H24A	0.6826	0.5860	−0.1055	0.094*
H24B	0.8287	0.6784	−0.1600	0.094*
H24C	0.8788	0.6528	−0.0550	0.094*
C25	0.9127 (2)	0.1091 (2)	−0.31191 (12)	0.0639 (4)
H25A	1.0028	0.0769	−0.2805	0.096*
H25B	0.9438	0.1264	−0.3755	0.096*
H25C	0.8005	0.0341	−0.3195	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.04190 (16)	0.04201 (16)	0.03897 (15)	0.01777 (12)	0.01525 (11)	0.01425 (11)
O1	0.0600 (6)	0.0618 (6)	0.0504 (5)	0.0199 (5)	0.0287 (5)	0.0245 (5)
O2	0.0553 (5)	0.0502 (5)	0.0523 (5)	0.0299 (4)	0.0170 (4)	0.0168 (4)
O3	0.0840 (8)	0.0512 (6)	0.0463 (5)	0.0219 (5)	0.0177 (5)	0.0221 (4)
O4	0.0694 (7)	0.0673 (7)	0.0392 (5)	0.0250 (5)	0.0174 (5)	0.0151 (4)
C1	0.0658 (9)	0.0351 (6)	0.0620 (9)	0.0165 (6)	0.0024 (7)	0.0124 (6)
C2	0.0685 (9)	0.0359 (6)	0.0768 (11)	0.0123 (6)	−0.0037 (8)	0.0224 (7)
C3	0.0503 (7)	0.0453 (7)	0.0676 (9)	0.0041 (6)	−0.0019 (6)	0.0296 (7)
C4	0.0456 (6)	0.0460 (7)	0.0551 (7)	0.0068 (5)	0.0065 (6)	0.0241 (6)
N5	0.0430 (5)	0.0359 (5)	0.0405 (5)	0.0118 (4)	0.0081 (4)	0.0140 (4)
C6	0.0494 (6)	0.0326 (5)	0.0367 (5)	0.0152 (4)	0.0084 (5)	0.0084 (4)
C7	0.0546 (7)	0.0358 (5)	0.0382 (6)	0.0146 (5)	0.0078 (5)	0.0103 (4)
C8	0.0482 (6)	0.0444 (6)	0.0377 (6)	0.0121 (5)	0.0051 (5)	0.0134 (5)
C9	0.0442 (6)	0.0520 (7)	0.0340 (5)	0.0147 (5)	0.0057 (5)	0.0088 (5)
C10	0.0513 (7)	0.0448 (6)	0.0381 (6)	0.0186 (5)	0.0072 (5)	0.0044 (5)
C11	0.0524 (7)	0.0340 (5)	0.0428 (6)	0.0173 (5)	0.0050 (5)	0.0054 (4)
C12	0.0426 (6)	0.0437 (6)	0.0313 (5)	0.0159 (5)	0.0085 (4)	0.0052 (4)
C13	0.0522 (7)	0.0612 (8)	0.0453 (7)	0.0092 (6)	0.0095 (6)	0.0198 (6)
C14	0.0506 (8)	0.0878 (12)	0.0531 (8)	−0.0009 (8)	0.0129 (7)	0.0152 (8)
C15	0.0437 (7)	0.0943 (13)	0.0579 (9)	0.0186 (8)	0.0040 (7)	−0.0083 (9)
C16	0.0676 (10)	0.0737 (11)	0.0762 (12)	0.0361 (9)	−0.0170 (9)	−0.0025 (9)
C17	0.0611 (8)	0.0498 (8)	0.0610 (9)	0.0184 (6)	−0.0082 (7)	0.0106 (6)
C18	0.0411 (6)	0.0313 (5)	0.0414 (6)	0.0105 (4)	0.0015 (4)	0.0084 (4)
C19	0.0370 (5)	0.0329 (5)	0.0356 (5)	0.0105 (4)	0.0036 (4)	0.0089 (4)
C20	0.0416 (6)	0.0327 (5)	0.0477 (6)	0.0089 (4)	−0.0004 (5)	0.0127 (5)
C21	0.0359 (5)	0.0349 (5)	0.0482 (6)	0.0065 (4)	0.0014 (5)	0.0157 (5)
C22	0.0417 (6)	0.0369 (5)	0.0362 (5)	0.0129 (4)	0.0036 (4)	0.0060 (4)
C23	0.0425 (6)	0.0337 (5)	0.0344 (5)	0.0112 (4)	0.0042 (4)	0.0074 (4)
C24	0.0872 (12)	0.0493 (8)	0.0610 (9)	0.0243 (8)	0.0164 (8)	0.0236 (7)
C25	0.0695 (10)	0.0806 (11)	0.0418 (7)	0.0277 (8)	0.0139 (7)	0.0017 (7)

Geometric parameters (Å, º) top

S1—O2	1.4231 (10)	C9—C10	1.3623 (19)
S1—O2	1.4231 (10)	C10—C22	1.4177 (17)
S1—O1	1.4251 (9)	C10—H10	0.93
S1—O1	1.4251 (9)	C11—C18	1.3712 (17)
S1—N5	1.6594 (11)	C11—C22	1.4060 (17)
S1—C12	1.7515 (13)	C11—H11	0.93
O3—C8	1.3564 (15)	C12—C17	1.3811 (19)
O3—C24	1.416 (2)	C12—C13	1.3816 (19)
O4—C9	1.3587 (15)	C13—C14	1.380 (2)
O4—C25	1.4183 (19)	C13—H13	0.93
C1—C2	1.381 (2)	C14—C15	1.376 (3)
C1—C20	1.3872 (18)	C14—H14	0.93
C1—H1	0.93	C15—C16	1.376 (3)
C2—C3	1.375 (3)	C15—H15	0.93
C2—H2	0.93	C16—C17	1.381 (2)
C3—C4	1.390 (2)	C16—H16	0.93
C3—H3	0.93	C17—H17	0.93
C4—C21	1.3909 (17)	C18—C19	1.4139 (16)
C4—H4	0.93	C18—C20	1.4494 (16)
N5—C19	1.4321 (14)	C20—C21	1.3950 (19)
N5—C21	1.4355 (15)	C22—C23	1.4196 (17)
C6—C19	1.3705 (15)	C24—H24A	0.96
C6—C23	1.4093 (16)	C24—H24B	0.96
C6—H6	0.93	C24—H24C	0.96
C7—C8	1.3637 (17)	C25—H25A	0.96
C7—C23	1.4215 (16)	C25—H25B	0.96
C7—H7	0.93	C25—H25C	0.96
C8—C9	1.4289 (19)

O2—S1—O1	119.60 (6)	C14—C13—C12	118.85 (16)
O2—S1—N5	106.42 (6)	C14—C13—H13	120.6
O1—S1—N5	106.38 (6)	C12—C13—H13	120.6
O2—S1—C12	109.08 (6)	C15—C14—C13	120.03 (17)
O2—S1—C12	109.08 (6)	C15—C14—H14	120.0
O1—S1—C12	109.33 (6)	C13—C14—H14	120.0
O1—S1—C12	109.33 (6)	C14—C15—C16	120.53 (15)
N5—S1—C12	105.02 (5)	C14—C15—H15	119.7
C8—O3—C24	117.66 (12)	C16—C15—H15	119.7
C9—O4—C25	116.75 (12)	C15—C16—C17	120.44 (17)
C2—C1—C20	118.78 (15)	C15—C16—H16	119.8
C2—C1—H1	120.6	C17—C16—H16	119.8
C20—C1—H1	120.6	C12—C17—C16	118.38 (16)
C3—C2—C1	120.75 (14)	C12—C17—H17	120.8
C3—C2—H2	119.6	C16—C17—H17	120.8
C1—C2—H2	119.6	C11—C18—C19	120.27 (11)
C2—C3—C4	121.93 (14)	C11—C18—C20	132.36 (11)
C2—C3—H3	119.0	C19—C18—C20	107.37 (11)
C4—C3—H3	119.0	C6—C19—C18	121.62 (11)
C3—C4—C21	117.01 (15)	C6—C19—N5	129.82 (10)
C3—C4—H4	121.5	C18—C19—N5	108.55 (9)
C21—C4—H4	121.5	C1—C20—C21	120.01 (12)
C19—N5—C21	107.00 (9)	C1—C20—C18	131.88 (13)
C19—N5—S1	120.99 (8)	C21—C20—C18	108.10 (11)
C21—N5—S1	122.60 (8)	C4—C21—C20	121.51 (12)
C19—C6—C23	118.47 (11)	C4—C21—N5	129.56 (13)
C19—C6—H6	120.8	C20—C21—N5	108.88 (10)
C23—C6—H6	120.8	C11—C22—C10	121.58 (11)
C8—C7—C23	121.15 (12)	C11—C22—C23	119.36 (11)
C8—C7—H7	119.4	C10—C22—C23	119.06 (11)
C23—C7—H7	119.4	C6—C23—C22	120.47 (11)
O3—C8—C7	125.72 (13)	C6—C23—C7	120.86 (11)
O3—C8—C9	114.26 (11)	C22—C23—C7	118.67 (11)
C7—C8—C9	120.02 (12)	O3—C24—H24A	109.5
O4—C9—C10	125.54 (12)	O3—C24—H24B	109.5
O4—C9—C8	114.56 (12)	H24A—C24—H24B	109.5
C10—C9—C8	119.89 (12)	O3—C24—H24C	109.5
C9—C10—C22	121.20 (12)	H24A—C24—H24C	109.5
C9—C10—H10	119.4	H24B—C24—H24C	109.5
C22—C10—H10	119.4	O4—C25—H25A	109.5
C18—C11—C22	119.80 (11)	O4—C25—H25B	109.5
C18—C11—H11	120.1	H25A—C25—H25B	109.5
C22—C11—H11	120.1	O4—C25—H25C	109.5
C17—C12—C13	121.76 (13)	H25A—C25—H25C	109.5
C17—C12—S1	118.76 (11)	H25B—C25—H25C	109.5
C13—C12—S1	119.47 (11)

O2—S1—O1—O1	0.00 (16)	C13—C14—C15—C16	0.0 (3)
O2—S1—O1—O1	0.00 (16)	C14—C15—C16—C17	−0.8 (3)
N5—S1—O1—O1	0.00 (14)	C13—C12—C17—C16	0.2 (2)
C12—S1—O1—O1	0.00 (17)	S1—C12—C17—C16	178.91 (12)
O1—S1—O2—O2	0.00 (14)	C15—C16—C17—C12	0.7 (3)
O1—S1—O2—O2	0.00 (14)	C22—C11—C18—C19	0.61 (19)
N5—S1—O2—O2	0.00 (15)	C22—C11—C18—C20	−179.99 (12)
C12—S1—O2—O2	0.00 (16)	C23—C6—C19—C18	−0.16 (18)
C20—C1—C2—C3	0.9 (2)	C23—C6—C19—N5	−178.68 (11)
C1—C2—C3—C4	−0.1 (2)	C11—C18—C19—C6	−0.69 (18)
C2—C3—C4—C21	−0.8 (2)	C20—C18—C19—C6	179.78 (11)
O2—S1—N5—C19	49.36 (10)	C11—C18—C19—N5	178.11 (11)
O2—S1—N5—C19	49.36 (10)	C20—C18—C19—N5	−1.42 (13)
O1—S1—N5—C19	177.92 (9)	C21—N5—C19—C6	−178.66 (12)
O1—S1—N5—C19	177.92 (9)	S1—N5—C19—C6	−31.42 (17)
C12—S1—N5—C19	−66.23 (10)	C21—N5—C19—C18	2.67 (12)
O2—S1—N5—C21	−168.55 (9)	S1—N5—C19—C18	149.90 (9)
O2—S1—N5—C21	−168.55 (9)	C2—C1—C20—C21	−0.9 (2)
O1—S1—N5—C21	−39.99 (11)	C2—C1—C20—C18	179.24 (14)
O1—S1—N5—C21	−39.99 (11)	C11—C18—C20—C1	0.0 (2)
C12—S1—N5—C21	75.86 (10)	C19—C18—C20—C1	179.45 (14)
C24—O3—C8—C7	−3.8 (2)	C11—C18—C20—C21	−179.87 (13)
C24—O3—C8—C9	175.91 (13)	C19—C18—C20—C21	−0.41 (13)
C23—C7—C8—O3	−179.89 (12)	C3—C4—C21—C20	0.81 (19)
C23—C7—C8—C9	0.4 (2)	C3—C4—C21—N5	178.13 (12)
C25—O4—C9—C10	6.8 (2)	C1—C20—C21—C4	0.02 (19)
C25—O4—C9—C8	−172.91 (13)	C18—C20—C21—C4	179.91 (11)
O3—C8—C9—O4	−1.32 (17)	C1—C20—C21—N5	−177.80 (12)
C7—C8—C9—O4	178.41 (12)	C18—C20—C21—N5	2.09 (13)
O3—C8—C9—C10	179.00 (12)	C19—N5—C21—C4	179.47 (12)
C7—C8—C9—C10	−1.3 (2)	S1—N5—C21—C4	32.88 (17)
O4—C9—C10—C22	−178.64 (12)	C19—N5—C21—C20	−2.94 (13)
C8—C9—C10—C22	1.0 (2)	S1—N5—C21—C20	−149.53 (9)
O2—S1—C12—C17	170.30 (11)	C18—C11—C22—C10	−179.74 (11)
O2—S1—C12—C17	170.30 (11)	C18—C11—C22—C23	0.28 (19)
O1—S1—C12—C17	37.83 (12)	C9—C10—C22—C11	−179.87 (12)
O1—S1—C12—C17	37.83 (12)	C9—C10—C22—C23	0.11 (19)
N5—S1—C12—C17	−75.97 (12)	C19—C6—C23—C22	1.07 (18)
O2—S1—C12—C13	−10.97 (13)	C19—C6—C23—C7	−179.10 (12)
O2—S1—C12—C13	−10.97 (13)	C11—C22—C23—C6	−1.14 (18)
O1—S1—C12—C13	−143.44 (11)	C10—C22—C23—C6	178.88 (11)
O1—S1—C12—C13	−143.44 (11)	C11—C22—C23—C7	179.02 (12)
N5—S1—C12—C13	102.76 (11)	C10—C22—C23—C7	−0.95 (18)
C17—C12—C13—C14	−1.0 (2)	C8—C7—C23—C6	−179.15 (12)
S1—C12—C13—C14	−179.69 (12)	C8—C7—C23—C22	0.7 (2)
C12—C13—C14—C15	0.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1	0.93	2.34	2.9238 (19)	120
C6—H6···O2	0.93	2.37	2.9674 (15)	122
C2—H2···O2ⁱ	0.93	2.55	3.3361 (17)	143
C24—H24C···Cg1ⁱⁱ	0.96	2.84	3.727 (2)	154
C25—H25A···Cg2ⁱⁱⁱ	0.96	2.90	3.628 (2)	134

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

Experimental details

Crystal data
Chemical formula	C₂₄H₁₉NO₄S
M_r	417.46
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.8606 (2), 9.5892 (2), 13.8846 (4)
α, β, γ (°)	100.387 (1), 93.168 (2), 105.883 (1)
V (Å³)	984.05 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.943, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	26246, 7025, 5372
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.773

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.138, 1.04
No. of reflections	7025
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.25

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

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1	0.93	2.34	2.9238 (19)	120
C6—H6···O2	0.93	2.37	2.9674 (15)	122
C2—H2···O2ⁱ	0.93	2.55	3.3361 (17)	143
C24—H24C···Cg1ⁱⁱ	0.96	2.84	3.7272 (21)	154
C25—H25A···Cg2ⁱⁱⁱ	0.96	2.90	3.6276 (21)	134

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

Acknowledgements

TK thanks the CSIR, India, for financial support in the form of a senior research fellowship.

References

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