1-(Phenyl-sulfon-yl)benzo[1,2:2',3']thieno[5',4'-b]carbazole.

In the title compound, C(24)H(15)NO(2)S(2), 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 inter-actions 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 = 413.49

Triclinic,

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[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.192

S = 1.01

6428 reflections

262 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.98 e Å−3

Δρmin = −0.62 e Å−3

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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010044/bt5204sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C24H15NO2S2	Z = 2
Mr = 413.49	F(000) = 428
Triclinic, P1	Dx = 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

Bruker APEXII CCD area-detector diffractometer	6428 independent reflections
Radiation source: fine-focus sealed tube	4863 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω and φ scans	θmax = 32.2°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.981, Tmax = 0.985	k = −15→15
24843 measured reflections	l = −18→17

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(Fo2) + (0.1079P)2 + 0.4678P] where P = (Fo2 + 2Fc2)/3
6428 reflections	(Δ/σ)max = 0.001
262 parameters	Δρmax = 0.98 e Å−3
3 restraints	Δρmin = −0.61 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .