6-Meth-oxy-9-phenyl-sulfonyl-2-(2-thien-yl)-9H-thieno[2,3-b]carbazole.

In the title compound, C(25)H(17)NO(3)S(3), the mean planes of the thieno[2,3-b]carbazole and phenyl rings are inclined at an angle of 63.6 (1)°. The mol-ecular structure features short intra-molecular C-H⋯O contacts and the crystal packing exhibits weak inter-molecular C-H⋯S and π-π inter-actions [centroid-to-centroid distances 3.734 (2)-3.888 (2) Å].

Related literature

For biological activities of carbazole derivatives, see: Diaz et al. (2002 ▶); Itoigawa et al. (2000 ▶); Ramsewak et al. (1999 ▶); Tachibana et al. (2001 ▶); Zhang et al. (2004 ▶). For the structures of closely related compounds, see: Chakkaravarthi et al. (2008a ▶,b ▶); Hökelek et al. (1998 ▶). For bond-length data, see: Allen et al. (1987 ▶). For graph-set notation, see: Etter et al. (1990 ▶). For general background, see: Govindasamy et al. (1998 ▶).

Experimental

Crystal data

C25H17NO3S3

M = 475.58

Orthorhombic,

a = 15.3900 (12) Å

b = 10.1269 (7) Å

c = 28.233 (2) Å

V = 4400.2 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.37 mm−1

T = 295 (2) K

0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEX2 diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.914, T max = 0.931

25628 measured reflections

5212 independent reflections

3570 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.175

S = 1.04

5212 reflections

290 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.55 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: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003493/bt2862sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003493/bt2862Isup2.hkl

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

C25H17NO3S3	F(000) = 1968
Mr = 475.58	Dx = 1.436 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6275 reflections
a = 15.3900 (12) Å	θ = 2.5–25.4°
b = 10.1269 (7) Å	µ = 0.37 mm−1
c = 28.233 (2) Å	T = 295 K
V = 4400.2 (6) Å3	Block, colourless
Z = 8	0.25 × 0.20 × 0.20 mm

Bruker Kappa APEX2 diffractometer	5212 independent reflections
Radiation source: fine-focus sealed tube	3570 reflections with I > 2σ(I)
graphite	Rint = 0.040
ω and φ scans	θmax = 27.8°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→20
Tmin = 0.914, Tmax = 0.931	k = −7→13
25628 measured reflections	l = −37→36

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0908P)2 + 2.7061P] where P = (Fo2 + 2Fc2)/3
5212 reflections	(Δ/σ)max < 0.001
290 parameters	Δρmax = 0.55 e Å−3
2 restraints	Δρmin = −0.55 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.93528 (19)	−0.0624 (3)	0.20557 (10)	0.0443 (6)
C2	0.8927 (2)	0.0321 (4)	0.23253 (11)	0.0603 (9)
H2	0.9211	0.1084	0.2423	0.072*
C3	0.8070 (3)	0.0097 (5)	0.24438 (14)	0.0821 (13)
H3	0.7772	0.0714	0.2625	0.099*
C4	0.7651 (3)	−0.1032 (6)	0.22961 (16)	0.0911 (14)
H4	0.7071	−0.1165	0.2376	0.109*
C5	0.8074 (3)	−0.1944 (5)	0.20365 (15)	0.0873 (14)
H5	0.7784	−0.2704	0.1940	0.105*
C6	0.8939 (2)	−0.1764 (4)	0.19114 (12)	0.0632 (9)
H6	0.9232	−0.2397	0.1734	0.076*
C7	0.98916 (17)	−0.0076 (3)	0.09633 (9)	0.0385 (6)
C8	1.00292 (18)	−0.1328 (3)	0.07857 (10)	0.0447 (7)
H8	1.0426	−0.1908	0.0921	0.054*
C9	0.95349 (18)	−0.1667 (3)	0.03908 (9)	0.0404 (6)
C10	0.87808 (19)	−0.2665 (3)	−0.03036 (10)	0.0432 (6)
C11	0.85167 (18)	−0.1409 (3)	−0.02240 (10)	0.0434 (6)
H11	0.8101	−0.0985	−0.0408	0.052*
C12	0.89407 (17)	−0.0797 (3)	0.01716 (9)	0.0403 (6)
C13	0.88459 (18)	0.0474 (3)	0.03532 (9)	0.0415 (6)
H13	0.8474	0.1075	0.0208	0.050*
C14	0.93126 (16)	0.0831 (3)	0.07524 (9)	0.0379 (6)
C15	0.93339 (17)	0.2031 (3)	0.10301 (9)	0.0395 (6)
C16	0.88881 (19)	0.3216 (3)	0.09834 (10)	0.0459 (7)
H16	0.8497	0.3349	0.0737	0.055*
C17	0.9044 (2)	0.4192 (3)	0.13154 (11)	0.0491 (7)
C18	0.9644 (2)	0.4001 (3)	0.16782 (11)	0.0528 (8)
H18	0.9740	0.4676	0.1896	0.063*
C19	1.0099 (2)	0.2840 (3)	0.17224 (10)	0.0501 (7)
H19	1.0509	0.2723	0.1961	0.060*
C20	0.99236 (17)	0.1851 (3)	0.13975 (9)	0.0417 (6)
C21	0.85065 (19)	−0.3600 (3)	−0.06662 (10)	0.0450 (6)
C22	0.89216 (19)	−0.4794 (3)	−0.08041 (10)	0.0460 (6)
H22	0.9418	−0.5142	−0.0664	0.055*
C23	0.8466 (2)	−0.5371 (3)	−0.11860 (12)	0.0569 (8)
H23	0.8657	−0.6131	−0.1339	0.068*
C24	0.7753 (2)	−0.4750 (4)	−0.13083 (13)	0.0664 (9)
H24	0.7385	−0.5036	−0.1548	0.080*
C25	0.7922 (3)	0.5579 (4)	0.10138 (15)	0.0769 (11)
H25A	0.8090	0.5441	0.0690	0.115*
H25B	0.7699	0.6459	0.1050	0.115*
H25C	0.7481	0.4953	0.1099	0.115*
N1	1.02958 (15)	0.0539 (2)	0.13643 (8)	0.0421 (5)
O1	1.08087 (14)	−0.1554 (2)	0.17329 (8)	0.0562 (6)
O2	1.08494 (15)	0.0508 (2)	0.21908 (8)	0.0604 (6)
O3	0.86577 (17)	0.5408 (2)	0.13127 (9)	0.0695 (7)
S1	1.04166 (5)	−0.03348 (8)	0.18631 (2)	0.0445 (2)
S2	0.95684 (5)	−0.31754 (8)	0.01006 (3)	0.0507 (2)
S3	0.75741 (7)	−0.33734 (10)	−0.09832 (4)	0.0750 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0485 (16)	0.0515 (16)	0.0329 (13)	0.0051 (13)	−0.0020 (11)	0.0074 (12)
C2	0.073 (2)	0.063 (2)	0.0449 (17)	0.0128 (17)	0.0092 (16)	0.0052 (15)
C3	0.085 (3)	0.096 (3)	0.065 (2)	0.036 (3)	0.031 (2)	0.021 (2)
C4	0.060 (2)	0.137 (4)	0.076 (3)	−0.010 (3)	0.019 (2)	0.016 (3)
C5	0.074 (3)	0.118 (4)	0.070 (3)	−0.037 (3)	0.020 (2)	−0.010 (2)
C6	0.067 (2)	0.073 (2)	0.0502 (18)	−0.0099 (18)	0.0100 (16)	−0.0031 (16)
C7	0.0345 (12)	0.0513 (16)	0.0297 (12)	−0.0015 (11)	0.0001 (10)	0.0009 (11)
C8	0.0442 (16)	0.0526 (17)	0.0372 (14)	0.0062 (13)	−0.0056 (12)	−0.0003 (12)
C9	0.0427 (14)	0.0433 (15)	0.0353 (13)	0.0000 (11)	0.0009 (11)	0.0000 (11)
C10	0.0455 (15)	0.0455 (15)	0.0386 (14)	−0.0005 (12)	−0.0039 (11)	0.0001 (12)
C11	0.0440 (15)	0.0464 (15)	0.0397 (14)	0.0008 (12)	−0.0085 (12)	0.0007 (12)
C12	0.0392 (14)	0.0467 (15)	0.0349 (13)	−0.0013 (11)	−0.0007 (11)	0.0003 (11)
C13	0.0398 (14)	0.0472 (15)	0.0376 (13)	0.0036 (12)	−0.0050 (11)	−0.0018 (12)
C14	0.0347 (13)	0.0459 (15)	0.0331 (13)	−0.0014 (11)	0.0012 (10)	−0.0010 (11)
C15	0.0373 (13)	0.0477 (15)	0.0335 (13)	−0.0042 (11)	0.0007 (10)	−0.0019 (11)
C16	0.0427 (15)	0.0526 (17)	0.0425 (15)	−0.0014 (13)	−0.0065 (12)	−0.0058 (13)
C17	0.0470 (15)	0.0495 (17)	0.0508 (17)	0.0020 (13)	−0.0015 (13)	−0.0084 (13)
C18	0.0599 (19)	0.0549 (18)	0.0437 (16)	−0.0056 (15)	−0.0068 (14)	−0.0108 (14)
C19	0.0535 (17)	0.0579 (18)	0.0388 (15)	−0.0058 (14)	−0.0109 (13)	−0.0043 (13)
C20	0.0381 (14)	0.0500 (16)	0.0370 (14)	−0.0040 (12)	−0.0011 (11)	−0.0007 (12)
C21	0.0501 (14)	0.0442 (15)	0.0407 (14)	−0.0049 (12)	−0.0022 (10)	0.0010 (12)
C22	0.0426 (15)	0.0519 (17)	0.0434 (15)	0.0052 (12)	−0.0069 (11)	−0.0041 (12)
C23	0.065 (2)	0.0474 (17)	0.0579 (18)	−0.0049 (15)	−0.0049 (14)	−0.0143 (14)
C24	0.067 (2)	0.065 (2)	0.067 (2)	−0.0017 (18)	−0.0189 (17)	−0.0188 (18)
C25	0.080 (3)	0.068 (2)	0.082 (3)	0.024 (2)	−0.022 (2)	−0.013 (2)
N1	0.0422 (12)	0.0502 (14)	0.0337 (11)	−0.0010 (10)	−0.0041 (9)	0.0006 (10)
O1	0.0533 (13)	0.0639 (13)	0.0514 (12)	0.0212 (11)	−0.0061 (10)	−0.0004 (10)
O2	0.0627 (14)	0.0726 (15)	0.0460 (12)	−0.0020 (11)	−0.0226 (10)	−0.0019 (11)
O3	0.0739 (16)	0.0571 (14)	0.0775 (17)	0.0132 (12)	−0.0235 (13)	−0.0201 (12)
S1	0.0414 (4)	0.0569 (5)	0.0353 (4)	0.0058 (3)	−0.0090 (3)	0.0010 (3)
S2	0.0622 (5)	0.0464 (4)	0.0435 (4)	0.0082 (3)	−0.0120 (3)	−0.0020 (3)
S3	0.0713 (6)	0.0670 (6)	0.0867 (7)	0.0164 (5)	−0.0298 (5)	−0.0227 (5)

C1—C6	1.380 (5)	C14—C15	1.446 (4)
C1—C2	1.388 (4)	C15—C16	1.389 (4)
C1—S1	1.750 (3)	C15—C20	1.390 (4)
C2—C3	1.379 (6)	C16—C17	1.383 (4)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.376 (7)	C17—O3	1.368 (4)
C3—H3	0.9300	C17—C18	1.393 (4)
C4—C5	1.347 (7)	C18—C19	1.374 (5)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.388 (5)	C19—C20	1.385 (4)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—N1	1.449 (4)
C7—C8	1.379 (4)	C21—C22	1.422 (4)
C7—C14	1.411 (4)	C21—S3	1.707 (3)
C7—N1	1.434 (3)	C22—C23	1.413 (4)
C8—C9	1.393 (4)	C22—H22	0.9300
C8—H8	0.9300	C23—C24	1.311 (5)
C9—C12	1.412 (4)	C23—H23	0.9300
C9—S2	1.734 (3)	C24—S3	1.692 (4)
C10—C11	1.354 (4)	C24—H24	0.9300
C10—C21	1.457 (4)	C25—O3	1.422 (4)
C10—S2	1.743 (3)	C25—H25A	0.9600
C11—C12	1.434 (4)	C25—H25B	0.9600
C11—H11	0.9300	C25—H25C	0.9600
C12—C13	1.394 (4)	N1—S1	1.674 (2)
C13—C14	1.384 (4)	O1—S1	1.422 (2)
C13—H13	0.9300	O2—S1	1.424 (2)
C6—C1—C2	121.4 (3)	C17—C16—C15	117.9 (3)
C6—C1—S1	118.7 (2)	C17—C16—H16	121.1
C2—C1—S1	119.8 (3)	C15—C16—H16	121.1
C3—C2—C1	118.1 (4)	O3—C17—C16	124.4 (3)
C3—C2—H2	121.0	O3—C17—C18	114.6 (3)
C1—C2—H2	121.0	C16—C17—C18	121.0 (3)
C4—C3—C2	120.8 (4)	C19—C18—C17	121.5 (3)
C4—C3—H3	119.6	C19—C18—H18	119.2
C2—C3—H3	119.6	C17—C18—H18	119.2
C5—C4—C3	120.5 (4)	C18—C19—C20	117.4 (3)
C5—C4—H4	119.7	C18—C19—H19	121.3
C3—C4—H4	119.7	C20—C19—H19	121.3
C4—C5—C6	120.8 (4)	C19—C20—C15	121.8 (3)
C4—C5—H5	119.6	C19—C20—N1	128.9 (3)
C6—C5—H5	119.6	C15—C20—N1	109.3 (2)
C1—C6—C5	118.5 (4)	C22—C21—C10	127.9 (3)
C1—C6—H6	120.7	C22—C21—S3	110.4 (2)
C5—C6—H6	120.7	C10—C21—S3	121.7 (2)
C8—C7—C14	122.8 (2)	C23—C22—C21	109.7 (3)
C8—C7—N1	128.3 (2)	C23—C22—H22	125.1
C14—C7—N1	108.9 (2)	C21—C22—H22	125.1
C7—C8—C9	115.7 (3)	C24—C23—C22	114.7 (3)
C7—C8—H8	122.2	C24—C23—H23	122.7
C9—C8—H8	122.2	C22—C23—H23	122.7
C8—C9—C12	123.4 (3)	C23—C24—S3	112.9 (3)
C8—C9—S2	125.4 (2)	C23—C24—H24	123.6
C12—C9—S2	111.2 (2)	S3—C24—H24	123.6
C11—C10—C21	129.8 (3)	O3—C25—H25A	109.5
C11—C10—S2	112.2 (2)	O3—C25—H25B	109.5
C21—C10—S2	118.0 (2)	H25A—C25—H25B	109.5
C10—C11—C12	113.5 (3)	O3—C25—H25C	109.5
C10—C11—H11	123.3	H25A—C25—H25C	109.5
C12—C11—H11	123.3	H25B—C25—H25C	109.5
C13—C12—C9	118.9 (2)	C7—N1—C20	106.1 (2)
C13—C12—C11	129.6 (3)	C7—N1—S1	118.85 (19)
C9—C12—C11	111.5 (2)	C20—N1—S1	118.30 (18)
C14—C13—C12	119.1 (3)	C17—O3—C25	117.3 (3)
C14—C13—H13	120.5	O1—S1—O2	119.31 (14)
C12—C13—H13	120.5	O1—S1—N1	106.77 (13)
C13—C14—C7	120.1 (3)	O2—S1—N1	106.37 (13)
C13—C14—C15	132.2 (3)	O1—S1—C1	109.39 (15)
C7—C14—C15	107.7 (2)	O2—S1—C1	109.64 (15)
C16—C15—C20	120.4 (3)	N1—S1—C1	104.24 (12)
C16—C15—C14	131.6 (2)	C9—S2—C10	91.58 (13)
C20—C15—C14	108.0 (2)	C24—S3—C21	92.11 (16)
C6—C1—C2—C3	−0.5 (5)	C16—C15—C20—C19	−1.1 (4)
S1—C1—C2—C3	175.8 (3)	C14—C15—C20—C19	179.0 (3)
C1—C2—C3—C4	−0.3 (6)	C16—C15—C20—N1	−179.9 (2)
C2—C3—C4—C5	0.7 (7)	C14—C15—C20—N1	0.2 (3)
C3—C4—C5—C6	−0.2 (7)	C11—C10—C21—C22	165.1 (3)
C2—C1—C6—C5	0.8 (5)	S2—C10—C21—C22	−14.8 (4)
S1—C1—C6—C5	−175.4 (3)	C11—C10—C21—S3	−16.4 (5)
C4—C5—C6—C1	−0.5 (6)	S2—C10—C21—S3	163.72 (17)
C14—C7—C8—C9	−2.2 (4)	C10—C21—C22—C23	−177.0 (3)
N1—C7—C8—C9	179.5 (3)	S3—C21—C22—C23	4.4 (3)
C7—C8—C9—C12	1.4 (4)	C21—C22—C23—C24	−3.9 (4)
C7—C8—C9—S2	−179.3 (2)	C22—C23—C24—S3	1.7 (4)
C21—C10—C11—C12	179.9 (3)	C8—C7—N1—C20	179.9 (3)
S2—C10—C11—C12	−0.2 (3)	C14—C7—N1—C20	1.4 (3)
C8—C9—C12—C13	0.8 (4)	C8—C7—N1—S1	−43.8 (4)
S2—C9—C12—C13	−178.6 (2)	C14—C7—N1—S1	137.7 (2)
C8—C9—C12—C11	−179.5 (3)	C19—C20—N1—C7	−179.6 (3)
S2—C9—C12—C11	1.2 (3)	C15—C20—N1—C7	−1.0 (3)
C10—C11—C12—C13	179.0 (3)	C19—C20—N1—S1	43.8 (4)
C10—C11—C12—C9	−0.7 (4)	C15—C20—N1—S1	−137.5 (2)
C9—C12—C13—C14	−2.3 (4)	C16—C17—O3—C25	13.9 (5)
C11—C12—C13—C14	178.0 (3)	C18—C17—O3—C25	−167.9 (3)
C12—C13—C14—C7	1.6 (4)	C7—N1—S1—O1	50.2 (2)
C12—C13—C14—C15	−177.5 (3)	C20—N1—S1—O1	−178.7 (2)
C8—C7—C14—C13	0.7 (4)	C7—N1—S1—O2	178.7 (2)
N1—C7—C14—C13	179.3 (2)	C20—N1—S1—O2	−50.3 (2)
C8—C7—C14—C15	−179.9 (2)	C7—N1—S1—C1	−65.5 (2)
N1—C7—C14—C15	−1.3 (3)	C20—N1—S1—C1	65.6 (2)
C13—C14—C15—C16	0.0 (5)	C6—C1—S1—O1	−22.2 (3)
C7—C14—C15—C16	−179.2 (3)	C2—C1—S1—O1	161.4 (2)
C13—C14—C15—C20	179.9 (3)	C6—C1—S1—O2	−154.8 (3)
C7—C14—C15—C20	0.7 (3)	C2—C1—S1—O2	28.9 (3)
C20—C15—C16—C17	−0.7 (4)	C6—C1—S1—N1	91.6 (3)
C14—C15—C16—C17	179.1 (3)	C2—C1—S1—N1	−84.7 (3)
C15—C16—C17—O3	179.6 (3)	C8—C9—S2—C10	179.6 (3)
C15—C16—C17—C18	1.5 (5)	C12—C9—S2—C10	−1.1 (2)
O3—C17—C18—C19	−178.7 (3)	C11—C10—S2—C9	0.7 (2)
C16—C17—C18—C19	−0.4 (5)	C21—C10—S2—C9	−179.4 (2)
C17—C18—C19—C20	−1.4 (5)	C23—C24—S3—C21	0.9 (3)
C18—C19—C20—C15	2.2 (4)	C22—C21—S3—C24	−3.1 (3)
C18—C19—C20—N1	−179.3 (3)	C10—C21—S3—C24	178.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.93	2.57	2.930 (4)	103
C8—H8···O1	0.93	2.39	2.940 (3)	117
C19—H19···O2	0.93	2.39	2.943 (4)	118
C22—H22···S2i	0.93	2.80	3.684 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1	0.93	2.57	2.930 (4)	103
C8—H8⋯O1	0.93	2.39	2.940 (3)	117
C19—H19⋯O2	0.93	2.39	2.943 (4)	118
C22—H22⋯S2i	0.93	2.80	3.684 (3)	158

Symmetry code: (i) .