7,9-Dimethyl-5-phenyl-sulfonyl-5H-benzo[b]carbazole.

In the title compound, C(24)H(19)NO(2)S, the mean plane of the benzo[b]carbazole ring system makes a dihedral angle of 79.26 (5)° with the phenyl ring. The S atom is in a distorted tetra-hedral configuration. The crystal structure exhibits weak C-H⋯O and C-H⋯π inter-actions.

Related literature

For related literature, see: Allen et al. (1987 ▶); Chakkaravarthi et al. (2007 ▶, 2008 ▶); Diaz et al. (2002 ▶); Etter et al. (1990 ▶); Friend et al. (1999 ▶); Govindasamy et al. (1998 ▶); Hökelek et al. (1998 ▶); Hosomi et al. (2000 ▶); Itoigawa et al. (2000 ▶); Ramsewak et al. (1999 ▶); Rodriguez et al. (1995 ▶); Sankaranarayanan et al. (2000 ▶); Tachibana et al. (2001 ▶); Zhang et al. (2004 ▶).

Experimental

Crystal data

C24H19NO2S

M = 385.46

Orthorhombic,

a = 13.9260 (6) Å

b = 10.1995 (5) Å

c = 27.3014 (14) Å

V = 3877.8 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.19 mm−1

T = 295 (2) K

0.30 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.940, T max = 0.971

26413 measured reflections

5626 independent reflections

3490 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.157

S = 1.04

5626 reflections

255 parameters

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: APEX2; 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/S1600536808024380/bt2759sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024380/bt2759Isup2.hkl

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

C24H19NO2S	F000 = 1616
Mr = 385.46	Dx = 1.320 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5907 reflections
a = 13.9260 (6) Å	θ = 2.6–28.4º
b = 10.1995 (5) Å	µ = 0.19 mm−1
c = 27.3014 (14) Å	T = 295 (2) K
V = 3877.8 (3) Å3	Block, colourless
Z = 8	0.30 × 0.20 × 0.16 mm

Bruker Kappa APEXII diffractometer	5626 independent reflections
Radiation source: fine-focus sealed tube	3490 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.038
T = 295(2) K	θmax = 30.0º
ω and φ scans	θmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −11→19
Tmin = 0.940, Tmax = 0.971	k = −14→11
26413 measured reflections	l = −37→38

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H-atom parameters constrained
wR(F2) = 0.157	w = 1/[σ2(Fo2) + (0.0716P)2 + 1.0437P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
5626 reflections	Δρmax = 0.68 e Å−3
255 parameters	Δρmin = −0.31 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
S1	0.53043 (3)	0.01070 (5)	0.179632 (16)	0.04540 (15)
O1	0.57705 (11)	0.10159 (16)	0.21087 (5)	0.0640 (4)
O2	0.58196 (10)	−0.09761 (15)	0.16030 (5)	0.0577 (4)
N1	0.49029 (11)	0.09650 (16)	0.13202 (5)	0.0426 (4)
C1	0.42667 (14)	−0.0487 (2)	0.20902 (7)	0.0477 (5)
C2	0.38759 (17)	−0.1665 (2)	0.19457 (8)	0.0591 (5)
H2	0.4160	−0.2151	0.1696	0.071*
C3	0.30584 (19)	−0.2116 (3)	0.21752 (10)	0.0772 (7)
H3	0.2787	−0.2909	0.2079	0.093*
C4	0.2648 (2)	−0.1411 (3)	0.25400 (11)	0.0809 (8)
H4	0.2099	−0.1727	0.2694	0.097*
C5	0.30312 (19)	−0.0243 (3)	0.26847 (10)	0.0785 (8)
H5	0.2741	0.0228	0.2936	0.094*
C6	0.38543 (18)	0.0250 (2)	0.24591 (8)	0.0627 (6)
H6	0.4117	0.1049	0.2554	0.075*
C7	0.44478 (13)	0.22122 (19)	0.13769 (7)	0.0454 (4)
C8	0.46434 (16)	0.3208 (2)	0.17055 (8)	0.0581 (5)
H8	0.5103	0.3106	0.1950	0.070*
C9	0.4132 (2)	0.4357 (3)	0.16576 (9)	0.0717 (7)
H9	0.4250	0.5042	0.1874	0.086*
C10	0.3448 (2)	0.4517 (3)	0.12961 (10)	0.0745 (7)
H10	0.3115	0.5304	0.1273	0.089*
C11	0.32554 (17)	0.3529 (2)	0.09714 (9)	0.0643 (6)
H11	0.2794	0.3642	0.0729	0.077*
C12	0.37554 (14)	0.2355 (2)	0.10081 (7)	0.0486 (5)
C13	0.37626 (13)	0.1181 (2)	0.07144 (6)	0.0446 (4)
C14	0.32703 (14)	0.0819 (2)	0.02981 (7)	0.0497 (5)
H14	0.2800	0.1367	0.0169	0.060*
C15	0.34814 (13)	−0.0379 (2)	0.00694 (7)	0.0491 (5)
C16	0.29952 (16)	−0.0775 (3)	−0.03650 (7)	0.0600 (6)
H16	0.2513	−0.0243	−0.0492	0.072*
C17	0.32182 (18)	−0.1911 (3)	−0.05996 (8)	0.0651 (7)
C18	0.39480 (18)	−0.2716 (2)	−0.04030 (8)	0.0648 (6)
H18	0.4103	−0.3488	−0.0566	0.078*
C19	0.44376 (15)	−0.2408 (2)	0.00171 (7)	0.0546 (5)
C20	0.42069 (14)	−0.12157 (19)	0.02648 (7)	0.0459 (4)
C21	0.47023 (13)	−0.08330 (19)	0.06929 (6)	0.0435 (4)
H21	0.5176	−0.1366	0.0827	0.052*
C22	0.44720 (12)	0.03323 (19)	0.09060 (6)	0.0410 (4)
C23	0.2711 (2)	−0.2323 (3)	−0.10647 (9)	0.0899 (9)
H23A	0.2321	−0.1613	−0.1182	0.135*
H23B	0.2312	−0.3070	−0.0999	0.135*
H23C	0.3179	−0.2549	−0.1309	0.135*
C24	0.5218 (2)	−0.3292 (2)	0.02088 (10)	0.0711 (7)
H24A	0.5012	−0.3687	0.0510	0.107*
H24B	0.5789	−0.2788	0.0266	0.107*
H24C	0.5350	−0.3966	−0.0027	0.107*

	U11	U22	U33	U12	U13	U23
S1	0.0375 (2)	0.0617 (3)	0.0370 (2)	0.0086 (2)	−0.00775 (18)	0.0004 (2)
O1	0.0572 (9)	0.0790 (11)	0.0557 (9)	0.0017 (8)	−0.0242 (7)	−0.0081 (8)
O2	0.0462 (7)	0.0755 (10)	0.0514 (8)	0.0223 (7)	−0.0049 (6)	−0.0018 (7)
N1	0.0413 (8)	0.0515 (9)	0.0350 (7)	−0.0009 (7)	−0.0056 (6)	0.0016 (7)
C1	0.0475 (10)	0.0575 (12)	0.0381 (9)	0.0151 (9)	0.0005 (8)	0.0109 (8)
C2	0.0635 (13)	0.0623 (14)	0.0514 (11)	0.0022 (11)	0.0064 (10)	0.0072 (10)
C3	0.0754 (17)	0.0786 (17)	0.0776 (17)	−0.0049 (14)	0.0120 (14)	0.0157 (14)
C4	0.0658 (16)	0.095 (2)	0.0812 (18)	0.0141 (15)	0.0191 (14)	0.0270 (16)
C5	0.0709 (16)	0.100 (2)	0.0647 (15)	0.0353 (16)	0.0233 (13)	0.0080 (14)
C6	0.0665 (14)	0.0663 (14)	0.0553 (12)	0.0216 (11)	0.0047 (11)	0.0011 (11)
C7	0.0436 (9)	0.0517 (11)	0.0410 (9)	−0.0013 (8)	−0.0029 (8)	0.0032 (8)
C8	0.0616 (13)	0.0608 (13)	0.0518 (11)	0.0015 (11)	−0.0108 (10)	−0.0044 (10)
C9	0.0864 (17)	0.0596 (14)	0.0690 (15)	0.0060 (13)	−0.0117 (13)	−0.0124 (12)
C10	0.0851 (18)	0.0611 (15)	0.0773 (17)	0.0192 (13)	−0.0111 (14)	−0.0043 (13)
C11	0.0618 (13)	0.0677 (15)	0.0635 (14)	0.0129 (11)	−0.0145 (11)	0.0051 (12)
C12	0.0450 (10)	0.0561 (12)	0.0446 (10)	0.0007 (9)	−0.0052 (8)	0.0056 (9)
C13	0.0387 (9)	0.0575 (11)	0.0376 (9)	−0.0068 (8)	−0.0033 (7)	0.0085 (8)
C14	0.0437 (10)	0.0622 (12)	0.0433 (10)	−0.0063 (9)	−0.0102 (8)	0.0104 (9)
C15	0.0440 (10)	0.0675 (13)	0.0359 (9)	−0.0200 (9)	−0.0030 (8)	0.0083 (9)
C16	0.0556 (12)	0.0824 (16)	0.0422 (10)	−0.0268 (11)	−0.0098 (9)	0.0062 (11)
C17	0.0692 (14)	0.0837 (17)	0.0425 (11)	−0.0398 (13)	−0.0033 (10)	−0.0006 (11)
C18	0.0757 (15)	0.0689 (15)	0.0499 (11)	−0.0344 (12)	0.0056 (11)	−0.0080 (11)
C19	0.0628 (12)	0.0549 (12)	0.0462 (10)	−0.0237 (10)	0.0041 (9)	0.0006 (9)
C20	0.0479 (10)	0.0532 (11)	0.0366 (9)	−0.0171 (8)	0.0035 (8)	0.0041 (8)
C21	0.0446 (10)	0.0500 (10)	0.0358 (9)	−0.0065 (8)	−0.0017 (7)	0.0058 (8)
C22	0.0381 (9)	0.0522 (11)	0.0329 (8)	−0.0072 (8)	−0.0026 (7)	0.0051 (7)
C23	0.099 (2)	0.117 (2)	0.0532 (13)	−0.0450 (19)	−0.0173 (13)	−0.0105 (15)
C24	0.0975 (19)	0.0495 (13)	0.0662 (15)	−0.0065 (13)	0.0034 (13)	−0.0067 (11)

S1—O1	1.4170 (15)	C11—H11	0.9300
S1—O2	1.4190 (15)	C12—C13	1.442 (3)
S1—N1	1.6636 (15)	C13—C14	1.377 (3)
S1—C1	1.760 (2)	C13—C22	1.414 (3)
N1—C7	1.430 (2)	C14—C15	1.404 (3)
N1—C22	1.434 (2)	C14—H14	0.9300
C1—C2	1.377 (3)	C15—C16	1.424 (3)
C1—C6	1.382 (3)	C15—C20	1.426 (3)
C2—C3	1.379 (3)	C16—C17	1.360 (4)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.355 (4)	C17—C18	1.412 (4)
C3—H3	0.9300	C17—C23	1.513 (3)
C4—C5	1.363 (4)	C18—C19	1.371 (3)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.395 (4)	C19—C20	1.428 (3)
C5—H5	0.9300	C19—C24	1.506 (3)
C6—H6	0.9300	C20—C21	1.412 (3)
C7—C8	1.382 (3)	C21—C22	1.362 (3)
C7—C12	1.402 (3)	C21—H21	0.9300
C8—C9	1.378 (3)	C23—H23A	0.9600
C8—H8	0.9300	C23—H23B	0.9600
C9—C10	1.381 (4)	C23—H23C	0.9600
C9—H9	0.9300	C24—H24A	0.9600
C10—C11	1.368 (3)	C24—H24B	0.9600
C10—H10	0.9300	C24—H24C	0.9600
C11—C12	1.388 (3)
O1—S1—O2	120.10 (9)	C7—C12—C13	107.97 (17)
O1—S1—N1	106.26 (9)	C14—C13—C22	119.30 (19)
O2—S1—N1	106.79 (8)	C14—C13—C12	132.68 (19)
O1—S1—C1	109.07 (10)	C22—C13—C12	107.91 (16)
O2—S1—C1	108.47 (10)	C13—C14—C15	119.73 (18)
N1—S1—C1	105.14 (8)	C13—C14—H14	120.1
C7—N1—C22	107.48 (14)	C15—C14—H14	120.1
C7—N1—S1	122.17 (12)	C14—C15—C16	121.2 (2)
C22—N1—S1	121.34 (13)	C14—C15—C20	120.20 (17)
C2—C1—C6	121.3 (2)	C16—C15—C20	118.6 (2)
C2—C1—S1	119.61 (16)	C17—C16—C15	121.7 (2)
C6—C1—S1	119.11 (19)	C17—C16—H16	119.2
C1—C2—C3	119.2 (2)	C15—C16—H16	119.2
C1—C2—H2	120.4	C16—C17—C18	118.7 (2)
C3—C2—H2	120.4	C16—C17—C23	121.7 (3)
C4—C3—C2	120.3 (3)	C18—C17—C23	119.5 (3)
C4—C3—H3	119.8	C19—C18—C17	122.9 (2)
C2—C3—H3	119.8	C19—C18—H18	118.6
C3—C4—C5	120.8 (3)	C17—C18—H18	118.6
C3—C4—H4	119.6	C18—C19—C20	118.6 (2)
C5—C4—H4	119.6	C18—C19—C24	120.8 (2)
C4—C5—C6	120.6 (2)	C20—C19—C24	120.51 (19)
C4—C5—H5	119.7	C21—C20—C15	119.36 (18)
C6—C5—H5	119.7	C21—C20—C19	121.15 (19)
C1—C6—C5	117.9 (3)	C15—C20—C19	119.46 (18)
C1—C6—H6	121.1	C22—C21—C20	118.67 (18)
C5—C6—H6	121.1	C22—C21—H21	120.7
C8—C7—C12	121.70 (19)	C20—C21—H21	120.7
C8—C7—N1	129.54 (17)	C21—C22—C13	122.74 (16)
C12—C7—N1	108.65 (17)	C21—C22—N1	129.15 (17)
C9—C8—C7	117.5 (2)	C13—C22—N1	107.99 (16)
C9—C8—H8	121.3	C17—C23—H23A	109.5
C7—C8—H8	121.3	C17—C23—H23B	109.5
C8—C9—C10	121.6 (2)	H23A—C23—H23B	109.5
C8—C9—H9	119.2	C17—C23—H23C	109.5
C10—C9—H9	119.2	H23A—C23—H23C	109.5
C11—C10—C9	120.7 (2)	H23B—C23—H23C	109.5
C11—C10—H10	119.6	C19—C24—H24A	109.5
C9—C10—H10	119.6	C19—C24—H24B	109.5
C10—C11—C12	119.3 (2)	H24A—C24—H24B	109.5
C10—C11—H11	120.3	C19—C24—H24C	109.5
C12—C11—H11	120.3	H24A—C24—H24C	109.5
C11—C12—C7	119.10 (19)	H24B—C24—H24C	109.5
C11—C12—C13	132.82 (18)
O1—S1—N1—C7	−43.11 (16)	C7—C12—C13—C14	−176.6 (2)
O2—S1—N1—C7	−172.43 (14)	C11—C12—C13—C22	175.6 (2)
C1—S1—N1—C7	72.46 (16)	C7—C12—C13—C22	−0.6 (2)
O1—S1—N1—C22	173.90 (14)	C22—C13—C14—C15	−0.3 (3)
O2—S1—N1—C22	44.58 (16)	C12—C13—C14—C15	175.41 (19)
C1—S1—N1—C22	−70.53 (16)	C13—C14—C15—C16	−179.16 (17)
O1—S1—C1—C2	−158.20 (16)	C13—C14—C15—C20	−0.4 (3)
O2—S1—C1—C2	−25.75 (18)	C14—C15—C16—C17	177.57 (19)
N1—S1—C1—C2	88.19 (17)	C20—C15—C16—C17	−1.2 (3)
O1—S1—C1—C6	22.46 (19)	C15—C16—C17—C18	0.4 (3)
O2—S1—C1—C6	154.91 (16)	C15—C16—C17—C23	−179.2 (2)
N1—S1—C1—C6	−91.15 (17)	C16—C17—C18—C19	0.6 (3)
C6—C1—C2—C3	−0.1 (3)	C23—C17—C18—C19	−179.9 (2)
S1—C1—C2—C3	−179.44 (18)	C17—C18—C19—C20	−0.6 (3)
C1—C2—C3—C4	−0.4 (4)	C17—C18—C19—C24	−179.3 (2)
C2—C3—C4—C5	0.4 (4)	C14—C15—C20—C21	0.7 (3)
C3—C4—C5—C6	0.0 (4)	C16—C15—C20—C21	179.44 (17)
C2—C1—C6—C5	0.5 (3)	C14—C15—C20—C19	−177.66 (17)
S1—C1—C6—C5	179.85 (17)	C16—C15—C20—C19	1.1 (3)
C4—C5—C6—C1	−0.5 (4)	C18—C19—C20—C21	−178.54 (18)
C22—N1—C7—C8	−176.3 (2)	C24—C19—C20—C21	0.2 (3)
S1—N1—C7—C8	36.3 (3)	C18—C19—C20—C15	−0.2 (3)
C22—N1—C7—C12	−0.2 (2)	C24—C19—C20—C15	178.47 (18)
S1—N1—C7—C12	−147.55 (14)	C15—C20—C21—C22	−0.2 (3)
C12—C7—C8—C9	−0.1 (3)	C19—C20—C21—C22	178.10 (16)
N1—C7—C8—C9	175.6 (2)	C20—C21—C22—C13	−0.5 (3)
C7—C8—C9—C10	0.0 (4)	C20—C21—C22—N1	−176.05 (17)
C8—C9—C10—C11	0.0 (4)	C14—C13—C22—C21	0.8 (3)
C9—C10—C11—C12	0.0 (4)	C12—C13—C22—C21	−175.89 (17)
C10—C11—C12—C7	−0.1 (3)	C14—C13—C22—N1	177.13 (16)
C10—C11—C12—C13	−175.9 (2)	C12—C13—C22—N1	0.5 (2)
C8—C7—C12—C11	0.2 (3)	C7—N1—C22—C21	175.86 (18)
N1—C7—C12—C11	−176.30 (18)	S1—N1—C22—C21	−36.4 (2)
C8—C7—C12—C13	176.93 (19)	C7—N1—C22—C13	−0.19 (19)
N1—C7—C12—C13	0.5 (2)	S1—N1—C22—C13	147.52 (13)
C11—C12—C13—C14	−0.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1	0.93	2.37	2.945 (3)	120
C21—H21···O2	0.93	2.34	2.935 (2)	122
C8—H8···Cg1i	0.93	3.00	3.859	155
C11—H11···Cg2ii	0.93	2.90	3.693	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1	0.93	2.37	2.945 (3)	120
C21—H21⋯O2	0.93	2.34	2.935 (2)	122
C8—H8⋯Cg1i	0.93	3.00	3.859	155
C11—H11⋯Cg2ii	0.93	2.90	3.693	144

Symmetry codes: (i) ; (ii) . Cg1 and Cg2 are the centroids of the C7–C12 and C15–C20 rings, respectively.