1-(Phenyl­sulfon­yl)benzo[1,2:2′,3′]thieno[5′,4′-b]carbazole

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

doi:10.1107/S1600536810010044

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o954

doi:10.1107/S1600536810010044

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1-(Phenylsulfonyl)benzo[1,2:2′,3′]thieno[5′,4′-b]carbazole

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: as_pandian59@yahoo.com

(Received 25 February 2010; accepted 17 March 2010; online 27 March 2010)

In the title compound, C₂₄H₁₅NO₂S₂, the ring system composed of the five fused rings is almost planar (r.m.s. deviation for all non-H atoms = 0.056 Å). The dihedral angle between the fused ring system and the phenyl ring is 83.4 (9)°. The crystal packing is stabilized by C—H⋯π and π–π interactions between parallel ring systems [centroid–centroid distances = 3.526 (3), 3.877 (3) and 3.712 (3) Å].

Related literature

For related structures, see: Murugavel et al. (2009 ); Chakkaravarthi et al. (2008 ); Ravishankar et al. (2005 ).

Experimental

Crystal data

C₂₄H₁₅NO₂S₂
M_r = 413.49
Triclinic, $[P \overline 1]$
a = 7.463 (5) Å
b = 10.462 (5) Å
c = 12.335 (5) Å
α = 80.438 (5)°
β = 89.433 (5)°
γ = 81.876 (5)°
V = 940.1 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.31 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
24843 measured reflections
6428 independent reflections
4863 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.192
S = 1.01
6428 reflections
262 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.98 e Å⁻³
Δρ_min = −0.62 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg6 is the centeroid of the C19–C24 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯Cg6ⁱ	0.93	2.78	3.685 (4)	166
Symmetry code: (i) -x+2, -y+1, -z+2.

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/S1600536810010044/bt5204sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810010044/bt5204Isup2.hkl

checkCIF report

Comment top

Carbazole and its derivatives have become quite attractive compounds owing to their applications in pharmacy and molecular electronics.

In order to obtain detailed information on molecular conformations in the solid state, an X-ray study of the title compound was carried out.

The ring system composed of the five rings is almost planar (r.m.s. deviation for all non-H atoms 0.056Å). The crystal packing is stabilized by C–H..O and C–H···π (Table. 1) hydrogen bonds. In addition, there are π–π interactions between the extended ring system with a mean distance between the ring planes of 3.7Å.

Related literature top

For related structures, see: Murugavel et al. (2009); Chakkaravarthi et al. (2008); Ravishankar et al. (2005).

Experimental top

To a solution of diethyl-2-((2-(bromomethyl)-1-(phenylsulfonyl)-1H-indol-3-yl) methylene)malonate (0.3 g 0.57 mmol) in dry 1,2-DCE (10 ml), InBr3 (0.02 g 0.06 mmol) and benzo[b]thiophene (0.09 g, 0.67 mmol) were added. The reaction mixture was stirred at room temperature for 4 h and then refluxed for 1 h under N2 atmosphere. It was then poured over ice-water (30 ml) containing 1 ml of Conc.HCl, extracted with chloroform (2 X 10 ml) and dried (Na₂SO₄). The removal of solvent followed by flash column chromatographic purification (silica gel, 230-420 mesh, n-hexane/ethyl acetate 99:1) afforded the product as a colorless solid. The product was recrystallization from CDCl₃

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 structure of showing the atom-numbering scheme and intramolecular hydrogen bond. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The molecular packing viewed down the a axis.

1-(Phenylsulfonyl)benzo[1,2:2',3']thieno[5',4'-b]carbazole top

Crystal data top

C₂₄H₁₅NO₂S₂	Z = 2
M_r = 413.49	F(000) = 428
Triclinic, P1	D_x = 1.461 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.463 (5) Å	Cell parameters from 6428 reflections
b = 10.462 (5) Å	θ = 1.7–32.2°
c = 12.335 (5) Å	µ = 0.31 mm⁻¹
α = 80.438 (5)°	T = 293 K
β = 89.433 (5)°	Block, white crystalline
γ = 81.876 (5)°	0.25 × 0.22 × 0.19 mm
V = 940.1 (9) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	6428 independent reflections
Radiation source: fine-focus sealed tube	4863 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω and ϕ scans	θ_max = 32.2°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.981, T_max = 0.985	k = −15→15
24843 measured reflections	l = −18→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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.192	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.1079P)² + 0.4678P] where P = (F_o² + 2F_c²)/3
6428 reflections	(Δ/σ)_max = 0.001
262 parameters	Δρ_max = 0.98 e Å⁻³
3 restraints	Δρ_min = −0.62 e Å⁻³

Crystal data top

C₂₄H₁₅NO₂S₂	γ = 81.876 (5)°
M_r = 413.49	V = 940.1 (9) Å³
Triclinic, P1	Z = 2
a = 7.463 (5) Å	Mo Kα radiation
b = 10.462 (5) Å	µ = 0.31 mm⁻¹
c = 12.335 (5) Å	T = 293 K
α = 80.438 (5)°	0.25 × 0.22 × 0.19 mm
β = 89.433 (5)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	6428 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4863 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.985	R_int = 0.024
24843 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	3 restraints
wR(F²) = 0.192	H-atom parameters constrained
S = 1.01	Δρ_max = 0.98 e Å⁻³
6428 reflections	Δρ_min = −0.62 e Å⁻³
262 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
C1	0.8004 (3)	0.5479 (2)	0.66419 (19)	0.0477 (5)
H1	0.8537	0.4628	0.6910	0.057*
C2	0.7893 (3)	0.5939 (3)	0.5527 (2)	0.0538 (5)
H2	0.8355	0.5391	0.5038	0.065*
C3	0.7106 (3)	0.7203 (3)	0.51279 (18)	0.0517 (5)
H3	0.7050	0.7491	0.4372	0.062*
C4	0.6398 (3)	0.8051 (2)	0.58229 (17)	0.0456 (4)
H4	0.5878	0.8904	0.5550	0.055*
C5	0.6495 (3)	0.75792 (19)	0.69390 (15)	0.0367 (4)
C6	0.7303 (3)	0.63112 (18)	0.73581 (16)	0.0368 (4)
C7	0.7156 (2)	0.61248 (17)	0.85389 (15)	0.0347 (3)
C8	0.6261 (2)	0.72886 (17)	0.88294 (15)	0.0344 (3)
C9	0.5880 (3)	0.74249 (19)	0.99044 (16)	0.0394 (4)
H9	0.5291	0.8202	1.0089	0.047*
C10	0.6430 (3)	0.63321 (19)	1.06946 (15)	0.0380 (4)
C11	0.7341 (2)	0.51533 (18)	1.04347 (15)	0.0360 (4)
C12	0.7710 (3)	0.50503 (19)	0.93443 (16)	0.0388 (4)
H12	0.8314	0.4279	0.9158	0.047*
C13	0.7743 (3)	0.4149 (2)	1.13958 (16)	0.0402 (4)
C14	0.8661 (3)	0.2850 (2)	1.1441 (2)	0.0502 (5)
H14	0.9123	0.2541	1.0815	0.060*
C15	0.8825 (4)	0.2076 (2)	1.2471 (2)	0.0564 (5)
H15	0.9393	0.1215	1.2554	0.068*
C16	0.8114 (3)	0.2611 (3)	1.34032 (18)	0.0531 (5)
H16	0.8280	0.2079	1.4088	0.064*
C17	0.7254 (4)	0.3785 (3)	1.3365 (2)	0.0593 (6)
H17	0.6768	0.4077	1.3992	0.071*
C18	0.7093 (3)	0.4578 (2)	1.23556 (18)	0.0482 (5)
C19	0.6988 (3)	1.05404 (18)	0.76966 (16)	0.0378 (4)
C20	0.7881 (3)	1.0581 (2)	0.86625 (19)	0.0478 (5)
H20	0.7459	1.0208	0.9336	0.057*
C21	0.9420 (3)	1.1189 (3)	0.8608 (2)	0.0579 (6)
H21	1.0036	1.1228	0.9250	0.070*
C22	1.0040 (4)	1.1735 (3)	0.7611 (3)	0.0606 (6)
H22	1.1082	1.2133	0.7581	0.073*
C23	0.9128 (4)	1.1697 (3)	0.6658 (2)	0.0648 (7)
H23	0.9549	1.2078	0.5987	0.078*
C24	0.7592 (3)	1.1098 (2)	0.6689 (2)	0.0517 (5)
H24	0.6974	1.1070	0.6044	0.062*
N1	0.5814 (2)	0.81927 (16)	0.78385 (13)	0.0385 (3)
O1	0.4119 (2)	1.01545 (15)	0.67159 (13)	0.0470 (3)
O2	0.4131 (2)	0.99247 (15)	0.87383 (13)	0.0461 (3)
S1	0.50484 (6)	0.97634 (4)	0.77433 (4)	0.03684 (13)
S2	0.60075 (9)	0.62317 (6)	1.20851 (5)	0.05295 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0510 (11)	0.0457 (11)	0.0460 (11)	0.0000 (9)	0.0036 (9)	−0.0127 (9)
C2	0.0555 (13)	0.0620 (14)	0.0468 (12)	−0.0036 (10)	0.0082 (10)	−0.0223 (10)
C3	0.0546 (12)	0.0650 (14)	0.0358 (10)	−0.0087 (10)	0.0050 (9)	−0.0093 (9)
C4	0.0495 (11)	0.0495 (11)	0.0351 (9)	−0.0042 (9)	−0.0001 (8)	−0.0014 (8)
C5	0.0378 (9)	0.0393 (9)	0.0331 (8)	−0.0059 (7)	0.0009 (7)	−0.0055 (7)
C6	0.0359 (8)	0.0373 (9)	0.0375 (9)	−0.0053 (7)	0.0006 (7)	−0.0064 (7)
C7	0.0342 (8)	0.0341 (8)	0.0356 (8)	−0.0046 (6)	0.0002 (6)	−0.0053 (6)
C8	0.0366 (8)	0.0312 (8)	0.0346 (8)	−0.0055 (6)	0.0005 (6)	−0.0026 (6)
C9	0.0485 (10)	0.0346 (8)	0.0348 (9)	−0.0041 (7)	0.0029 (7)	−0.0070 (7)
C10	0.0439 (10)	0.0366 (9)	0.0348 (8)	−0.0096 (7)	0.0007 (7)	−0.0067 (7)
C11	0.0358 (8)	0.0364 (8)	0.0351 (8)	−0.0065 (7)	−0.0028 (7)	−0.0027 (6)
C12	0.0414 (9)	0.0351 (8)	0.0389 (9)	−0.0019 (7)	0.0001 (7)	−0.0065 (7)
C13	0.0391 (9)	0.0427 (8)	0.0385 (9)	−0.0114 (7)	−0.0037 (7)	−0.0006 (7)
C14	0.0469 (11)	0.0470 (9)	0.0523 (12)	−0.0071 (8)	−0.0063 (9)	0.0053 (9)
C15	0.0573 (13)	0.0452 (11)	0.0607 (12)	−0.0046 (10)	−0.0072 (10)	0.0071 (9)
C16	0.0505 (12)	0.0673 (12)	0.0383 (9)	−0.0205 (9)	−0.0106 (8)	0.0116 (8)
C17	0.0689 (15)	0.0661 (12)	0.0443 (11)	−0.0252 (10)	−0.0056 (11)	−0.0001 (10)
C18	0.0519 (12)	0.0587 (13)	0.0379 (10)	−0.0244 (10)	−0.0010 (8)	−0.0053 (9)
C19	0.0377 (9)	0.0340 (8)	0.0402 (9)	−0.0014 (7)	0.0009 (7)	−0.0051 (7)
C20	0.0466 (11)	0.0518 (12)	0.0438 (11)	−0.0014 (9)	−0.0003 (8)	−0.0093 (9)
C21	0.0500 (13)	0.0619 (14)	0.0647 (15)	−0.0057 (10)	−0.0092 (11)	−0.0199 (12)
C22	0.0475 (12)	0.0555 (14)	0.0813 (18)	−0.0152 (10)	0.0011 (12)	−0.0116 (12)
C23	0.0622 (15)	0.0656 (16)	0.0658 (16)	−0.0245 (13)	0.0082 (12)	0.0045 (12)
C24	0.0561 (13)	0.0546 (12)	0.0434 (11)	−0.0166 (10)	0.0006 (9)	0.0021 (9)
N1	0.0475 (9)	0.0335 (7)	0.0325 (7)	−0.0013 (6)	0.0013 (6)	−0.0033 (6)
O1	0.0434 (8)	0.0467 (8)	0.0464 (8)	0.0002 (6)	−0.0085 (6)	0.0007 (6)
O2	0.0452 (8)	0.0437 (8)	0.0460 (8)	0.0023 (6)	0.0109 (6)	−0.0060 (6)
S1	0.0362 (2)	0.0344 (2)	0.0371 (2)	−0.00038 (16)	0.00092 (17)	−0.00168 (16)
S2	0.0709 (4)	0.0497 (3)	0.0405 (3)	−0.0133 (3)	0.0044 (2)	−0.0102 (2)

Geometric parameters (Å, º) top

C1—C2	1.379 (3)	C14—C15	1.386 (3)
C1—C6	1.389 (3)	C14—H14	0.9300
C1—H1	0.9300	C15—C16	1.426 (4)
C2—C3	1.381 (4)	C15—H15	0.9300
C2—H2	0.9300	C16—C17	1.297 (4)
C3—C4	1.383 (3)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.372 (3)
C4—C5	1.382 (3)	C17—H17	0.9300
C4—H4	0.9300	C18—S2	1.783 (3)
C5—C6	1.394 (3)	C19—C20	1.381 (3)
C5—N1	1.427 (2)	C19—C24	1.382 (3)
C6—C7	1.442 (3)	C19—S1	1.753 (2)
C7—C12	1.388 (3)	C20—C21	1.385 (4)
C7—C8	1.403 (3)	C20—H20	0.9300
C8—C9	1.380 (3)	C21—C22	1.371 (4)
C8—N1	1.426 (2)	C21—H21	0.9300
C9—C10	1.389 (3)	C22—C23	1.373 (4)
C9—H9	0.9300	C22—H22	0.9300
C10—C11	1.406 (3)	C23—C24	1.380 (4)
C10—S2	1.729 (2)	C23—H23	0.9300
C11—C12	1.389 (3)	C24—H24	0.9300
C11—C13	1.450 (3)	N1—S1	1.6469 (18)
C12—H12	0.9300	O1—S1	1.4212 (16)
C13—C18	1.393 (3)	O2—S1	1.4223 (16)
C13—C14	1.425 (3)

C2—C1—C6	118.7 (2)	C13—C14—H14	122.0
C2—C1—H1	120.6	C14—C15—C16	119.5 (2)
C6—C1—H1	120.6	C14—C15—H15	120.3
C1—C2—C3	120.7 (2)	C16—C15—H15	120.3
C1—C2—H2	119.6	C17—C16—C15	124.7 (2)
C3—C2—H2	119.6	C17—C16—H16	117.6
C2—C3—C4	121.7 (2)	C15—C16—H16	117.6
C2—C3—H3	119.1	C16—C17—C18	116.9 (3)
C4—C3—H3	119.1	C16—C17—H17	121.5
C5—C4—C3	117.2 (2)	C18—C17—H17	121.5
C5—C4—H4	121.4	C17—C18—C13	122.7 (3)
C3—C4—H4	121.4	C17—C18—S2	125.7 (2)
C4—C5—C6	121.90 (19)	C13—C18—S2	111.53 (16)
C4—C5—N1	129.92 (19)	C20—C19—C24	121.4 (2)
C6—C5—N1	108.16 (16)	C20—C19—S1	119.55 (16)
C1—C6—C5	119.68 (19)	C24—C19—S1	119.07 (17)
C1—C6—C7	132.31 (19)	C19—C20—C21	118.7 (2)
C5—C6—C7	107.97 (16)	C19—C20—H20	120.7
C12—C7—C8	120.30 (17)	C21—C20—H20	120.7
C12—C7—C6	131.54 (17)	C22—C21—C20	120.4 (2)
C8—C7—C6	108.15 (16)	C22—C21—H21	119.8
C9—C8—C7	122.62 (17)	C20—C21—H21	119.8
C9—C8—N1	129.72 (17)	C21—C22—C23	120.3 (2)
C7—C8—N1	107.63 (16)	C21—C22—H22	119.9
C8—C9—C10	116.03 (18)	C23—C22—H22	119.9
C8—C9—H9	122.0	C22—C23—C24	120.5 (3)
C10—C9—H9	122.0	C22—C23—H23	119.7
C9—C10—C11	122.92 (18)	C24—C23—H23	119.7
C9—C10—S2	124.73 (16)	C23—C24—C19	118.7 (2)
C11—C10—S2	112.31 (14)	C23—C24—H24	120.6
C12—C11—C10	119.59 (17)	C19—C24—H24	120.6
C12—C11—C13	127.69 (18)	C8—N1—C5	108.07 (15)
C10—C11—C13	112.69 (18)	C8—N1—S1	126.27 (13)
C7—C12—C11	118.53 (17)	C5—N1—S1	124.47 (13)
C7—C12—H12	120.7	O1—S1—O2	120.28 (10)
C11—C12—H12	120.7	O1—S1—N1	106.82 (9)
C18—C13—C14	120.1 (2)	O2—S1—N1	106.80 (9)
C18—C13—C11	112.01 (19)	O1—S1—C19	108.43 (10)
C14—C13—C11	127.9 (2)	O2—S1—C19	108.38 (10)
C15—C14—C13	116.0 (2)	N1—S1—C19	105.12 (10)
C15—C14—H14	122.0	C10—S2—C18	91.45 (10)

C6—C1—C2—C3	0.1 (4)	C15—C16—C17—C18	−2.9 (4)
C1—C2—C3—C4	−0.1 (4)	C16—C17—C18—C13	2.7 (4)
C2—C3—C4—C5	−0.6 (4)	C16—C17—C18—S2	−179.09 (18)
C3—C4—C5—C6	1.3 (3)	C14—C13—C18—C17	−1.7 (3)
C3—C4—C5—N1	−176.6 (2)	C11—C13—C18—C17	177.6 (2)
C2—C1—C6—C5	0.5 (3)	C14—C13—C18—S2	179.82 (16)
C2—C1—C6—C7	177.8 (2)	C11—C13—C18—S2	−0.8 (2)
C4—C5—C6—C1	−1.3 (3)	C24—C19—C20—C21	−0.4 (3)
N1—C5—C6—C1	177.01 (18)	S1—C19—C20—C21	179.44 (18)
C4—C5—C6—C7	−179.18 (18)	C19—C20—C21—C22	−0.2 (4)
N1—C5—C6—C7	−0.9 (2)	C20—C21—C22—C23	0.7 (4)
C1—C6—C7—C12	1.5 (4)	C21—C22—C23—C24	−0.7 (5)
C5—C6—C7—C12	179.1 (2)	C22—C23—C24—C19	0.1 (4)
C1—C6—C7—C8	−177.7 (2)	C20—C19—C24—C23	0.4 (4)
C5—C6—C7—C8	−0.2 (2)	S1—C19—C24—C23	−179.4 (2)
C12—C7—C8—C9	−0.4 (3)	C9—C8—N1—C5	−179.31 (19)
C6—C7—C8—C9	178.97 (17)	C7—C8—N1—C5	−1.7 (2)
C12—C7—C8—N1	−178.20 (17)	C9—C8—N1—S1	12.8 (3)
C6—C7—C8—N1	1.1 (2)	C7—C8—N1—S1	−169.59 (14)
C7—C8—C9—C10	−0.3 (3)	C4—C5—N1—C8	179.7 (2)
N1—C8—C9—C10	176.99 (18)	C6—C5—N1—C8	1.6 (2)
C8—C9—C10—C11	0.8 (3)	C4—C5—N1—S1	−12.1 (3)
C8—C9—C10—S2	−176.55 (14)	C6—C5—N1—S1	169.78 (14)
C9—C10—C11—C12	−0.6 (3)	C8—N1—S1—O1	−156.86 (17)
S2—C10—C11—C12	177.07 (15)	C5—N1—S1—O1	37.10 (18)
C9—C10—C11—C13	−178.95 (18)	C8—N1—S1—O2	−27.0 (2)
S2—C10—C11—C13	−1.3 (2)	C5—N1—S1—O2	167.01 (16)
C8—C7—C12—C11	0.6 (3)	C8—N1—S1—C19	88.06 (18)
C6—C7—C12—C11	−178.54 (19)	C5—N1—S1—C19	−77.97 (17)
C10—C11—C12—C7	−0.2 (3)	C20—C19—S1—O1	164.32 (16)
C13—C11—C12—C7	177.95 (18)	C24—C19—S1—O1	−15.8 (2)
C12—C11—C13—C18	−176.85 (19)	C20—C19—S1—O2	32.19 (19)
C10—C11—C13—C18	1.4 (2)	C24—C19—S1—O2	−147.95 (18)
C12—C11—C13—C14	2.4 (3)	C20—C19—S1—N1	−81.72 (18)
C10—C11—C13—C14	−179.34 (19)	C24—C19—S1—N1	98.14 (19)
C18—C13—C14—C15	0.8 (3)	C9—C10—S2—C18	178.30 (19)
C11—C13—C14—C15	−178.4 (2)	C11—C10—S2—C18	0.71 (15)
C13—C14—C15—C16	−1.0 (3)	C17—C18—S2—C10	−178.3 (2)
C14—C15—C16—C17	2.2 (4)	C13—C18—S2—C10	0.08 (16)

Hydrogen-bond geometry (Å, º) top

Cg6 is the centeroid of the C19–C24 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···Cg6ⁱ	0.93	2.78	3.685 (4)	166

Symmetry code: (i) −x+2, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₅NO₂S₂
M_r	413.49
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.463 (5), 10.462 (5), 12.335 (5)
α, β, γ (°)	80.438 (5), 89.433 (5), 81.876 (5)
V (Å³)	940.1 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
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	24843, 6428, 4863
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.750

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.192, 1.01
No. of reflections	6428
No. of parameters	262
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.98, −0.62

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

Cg6 is the centeroid of the C19–C24 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···Cg6ⁱ	0.93	2.78	3.685 (4)	166

Symmetry code: (i) −x+2, −y+1, −z+2.

Acknowledgements

ST and ASP thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

References

Bruker (2004). APEX2 and SAINT. 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
Murugavel, S., Ranjith, S., SubbiahPandi, A., Periyasami, G. & Raghunathan, R. (2009). Acta Cryst. E65, o139–o140. Web of Science CSD CrossRef IUCr Journals 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
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 4| April 2010| Page o954

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