8,9-Dimeth-oxy-5-phenyl-sulfonyl-5H-benzo[b]carbazole.

In the title compound, C(24)H(19)NO(4)S, 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. Intra-molecular C-H⋯O inter-actions are observed. A C(8) chain running along the b axis is formed via inter-molecular C-H⋯O hydrogen bonds. The chains are linked via weak C-H⋯ π inter-actions.

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 = 417.46

Triclinic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.138

S = 1.04

7025 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.25 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 I, global. DOI: 10.1107/S160053681001247X/ci5059sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001247X/ci5059Isup2.hkl

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

C24H19NO4S	Z = 2
Mr = 417.46	F(000) = 436
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0749P)2 + 0.1333P] where P = (Fo2 + 2Fc2)/3
7025 reflections	(Δ/σ)max = 0.001
273 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.25 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
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*

	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)

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)

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

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) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C7–C10/C22/C23 and C1–C4/C21/C20 rings, respectively.