9-Meth-oxy-5-phenyl-sulfonyl-5H-benzo[b]carbazole.

In the title compound, C(23)H(17)NO(3)S, the mean plane of the benzo[b]carbazole ring system makes a dihedral angle of 77.17 (4)° with the phenyl ring. The S atom is in a distorted tetra-hedral configuration. There are three intra-molecular C-H⋯O inter-actions forming five- and six-membered rings with graph-set motifs S(5) and S(6), respectively.

Related literature

For related literature, see: Allen et al. (1987 ▶); Chakkaravarthi et al. (2007 ▶, 2008 ▶); Diaz et al. (2002 ▶); Etter et al. (1990 ▶); 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

C23H17NO3S

M = 387.44

Triclinic,

a = 8.3608 (3) Å

b = 9.3103 (3) Å

c = 12.1754 (4) Å

α = 76.061 (2)°

β = 88.680 (1)°

γ = 88.715 (2)°

V = 919.46 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 295 (2) K

0.30 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEX2 diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.909, T max = 0.969

23200 measured reflections

5739 independent reflections

4330 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.134

S = 1.05

5739 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.35 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/S1600536808024756/bt2761sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024756/bt2761Isup2.hkl

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

C23H17NO3S	Z = 2
Mr = 387.44	F000 = 404
Triclinic, P1	Dx = 1.399 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.3608 (3) Å	Cell parameters from 6534 reflections
b = 9.3103 (3) Å	θ = 2.4–30.7º
c = 12.1754 (4) Å	µ = 0.20 mm−1
α = 76.061 (2)º	T = 295 (2) K
β = 88.6800 (10)º	Block, colourless
γ = 88.715 (2)º	0.30 × 0.20 × 0.16 mm
V = 919.46 (5) Å3

Bruker Kappa APEX2 diffractometer	5739 independent reflections
Radiation source: fine-focus sealed tube	4330 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.022
T = 295(2) K	θmax = 30.9º
ω and φ scans	θmin = 2.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.909, Tmax = 0.969	k = −12→13
23200 measured reflections	l = −17→17

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.134	w = 1/[σ2(Fo2) + (0.0653P)2 + 0.1785P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
5739 reflections	Δρmax = 0.29 e Å−3
254 parameters	Δρmin = −0.35 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
S1	0.46793 (4)	0.47800 (4)	0.77672 (3)	0.04613 (11)
O1	0.54144 (15)	0.52427 (14)	0.66788 (10)	0.0629 (3)
O2	0.55193 (14)	0.49026 (13)	0.87398 (10)	0.0595 (3)
O3	0.19450 (16)	−0.22782 (14)	1.37354 (9)	0.0650 (3)
N1	0.42588 (14)	0.30123 (12)	0.79458 (9)	0.0434 (2)
C1	0.28152 (18)	0.56690 (14)	0.77467 (12)	0.0473 (3)
C2	0.2064 (2)	0.57404 (18)	0.87596 (15)	0.0616 (4)
H2	0.2572	0.5391	0.9447	0.074*
C3	0.0533 (3)	0.6349 (2)	0.8715 (2)	0.0820 (6)
H3	−0.0003	0.6411	0.9380	0.098*
C4	−0.0204 (3)	0.6865 (2)	0.7683 (3)	0.0895 (7)
H4	−0.1243	0.7246	0.7663	0.107*
C5	0.0581 (3)	0.6822 (2)	0.6692 (2)	0.0845 (7)
H5	0.0085	0.7199	0.6004	0.101*
C6	0.2093 (2)	0.62243 (18)	0.67116 (15)	0.0635 (4)
H6	0.2631	0.6191	0.6041	0.076*
C7	0.35493 (16)	0.24535 (15)	0.70734 (11)	0.0419 (3)
C8	0.37507 (19)	0.29073 (17)	0.59112 (12)	0.0512 (3)
H8	0.4363	0.3725	0.5579	0.061*
C9	0.3005 (2)	0.20949 (19)	0.52609 (13)	0.0578 (4)
H9	0.3115	0.2377	0.4477	0.069*
C10	0.2101 (2)	0.0875 (2)	0.57509 (13)	0.0602 (4)
H10	0.1620	0.0347	0.5294	0.072*
C11	0.1905 (2)	0.04329 (18)	0.69090 (13)	0.0540 (4)
H11	0.1295	−0.0388	0.7237	0.065*
C12	0.26309 (16)	0.12316 (15)	0.75771 (11)	0.0427 (3)
C13	0.27196 (15)	0.10092 (14)	0.87926 (11)	0.0409 (3)
C14	0.20944 (17)	−0.00631 (16)	0.96676 (12)	0.0457 (3)
H14	0.1427	−0.0777	0.9521	0.055*
C15	0.24777 (16)	−0.00676 (15)	1.07919 (11)	0.0428 (3)
C16	0.19098 (19)	−0.11947 (17)	1.17162 (12)	0.0504 (3)
H16	0.1228	−0.1911	1.1589	0.060*
C17	0.23668 (18)	−0.12252 (17)	1.27913 (12)	0.0498 (3)
C18	0.33749 (19)	−0.01305 (17)	1.29944 (12)	0.0516 (3)
H18	0.3674	−0.0160	1.3731	0.062*
C19	0.39146 (19)	0.09670 (16)	1.21281 (12)	0.0486 (3)
H19	0.4572	0.1686	1.2280	0.058*
C20	0.34939 (16)	0.10378 (14)	1.09928 (11)	0.0419 (3)
C21	0.41158 (17)	0.21431 (15)	1.00847 (12)	0.0444 (3)
H21	0.4774	0.2874	1.0216	0.053*
C22	0.37207 (15)	0.21053 (14)	0.90096 (11)	0.0398 (3)
C23	0.1076 (2)	−0.3496 (2)	1.35768 (15)	0.0671 (5)
H23A	0.0031	−0.3164	1.3303	0.101*
H23B	0.0974	−0.4218	1.4284	0.101*
H23C	0.1632	−0.3932	1.3036	0.101*

	U11	U22	U33	U12	U13	U23
S1	0.0454 (2)	0.04688 (19)	0.04625 (18)	−0.01263 (14)	0.00349 (13)	−0.01082 (13)
O1	0.0640 (7)	0.0674 (7)	0.0561 (6)	−0.0223 (6)	0.0174 (5)	−0.0124 (5)
O2	0.0592 (7)	0.0604 (6)	0.0604 (6)	−0.0184 (5)	−0.0094 (5)	−0.0151 (5)
O3	0.0758 (8)	0.0647 (7)	0.0478 (6)	−0.0110 (6)	−0.0011 (5)	0.0005 (5)
N1	0.0449 (6)	0.0423 (5)	0.0435 (5)	−0.0045 (5)	0.0008 (4)	−0.0115 (4)
C1	0.0536 (8)	0.0348 (6)	0.0532 (7)	−0.0069 (5)	0.0004 (6)	−0.0094 (5)
C2	0.0682 (10)	0.0485 (8)	0.0638 (9)	−0.0045 (7)	0.0141 (8)	−0.0062 (7)
C3	0.0766 (13)	0.0555 (10)	0.1082 (17)	0.0014 (9)	0.0332 (12)	−0.0121 (10)
C4	0.0642 (12)	0.0570 (11)	0.145 (2)	0.0128 (9)	−0.0064 (14)	−0.0210 (13)
C5	0.0874 (15)	0.0581 (11)	0.1115 (18)	0.0186 (10)	−0.0349 (14)	−0.0258 (11)
C6	0.0789 (12)	0.0500 (8)	0.0634 (9)	0.0034 (8)	−0.0149 (8)	−0.0160 (7)
C7	0.0396 (6)	0.0440 (6)	0.0445 (6)	0.0008 (5)	0.0015 (5)	−0.0154 (5)
C8	0.0554 (8)	0.0526 (8)	0.0460 (7)	−0.0061 (6)	0.0064 (6)	−0.0129 (6)
C9	0.0680 (10)	0.0649 (9)	0.0428 (7)	−0.0058 (8)	0.0028 (6)	−0.0177 (6)
C10	0.0701 (11)	0.0673 (10)	0.0492 (8)	−0.0115 (8)	−0.0030 (7)	−0.0243 (7)
C11	0.0595 (9)	0.0555 (8)	0.0503 (7)	−0.0133 (7)	0.0001 (6)	−0.0182 (6)
C12	0.0406 (7)	0.0464 (7)	0.0429 (6)	−0.0011 (5)	0.0010 (5)	−0.0146 (5)
C13	0.0369 (6)	0.0435 (6)	0.0434 (6)	0.0003 (5)	−0.0011 (5)	−0.0129 (5)
C14	0.0434 (7)	0.0473 (7)	0.0474 (7)	−0.0078 (5)	−0.0011 (5)	−0.0127 (5)
C15	0.0395 (6)	0.0437 (6)	0.0445 (6)	0.0013 (5)	−0.0003 (5)	−0.0098 (5)
C16	0.0492 (8)	0.0508 (7)	0.0490 (7)	−0.0055 (6)	0.0005 (6)	−0.0076 (6)
C17	0.0495 (8)	0.0499 (7)	0.0464 (7)	0.0041 (6)	0.0003 (6)	−0.0051 (6)
C18	0.0587 (9)	0.0516 (8)	0.0447 (7)	0.0086 (6)	−0.0078 (6)	−0.0121 (6)
C19	0.0534 (8)	0.0458 (7)	0.0486 (7)	0.0031 (6)	−0.0076 (6)	−0.0149 (6)
C20	0.0410 (7)	0.0411 (6)	0.0446 (6)	0.0053 (5)	−0.0027 (5)	−0.0126 (5)
C21	0.0455 (7)	0.0404 (6)	0.0490 (7)	−0.0019 (5)	−0.0039 (5)	−0.0133 (5)
C22	0.0373 (6)	0.0385 (6)	0.0438 (6)	0.0012 (5)	0.0000 (5)	−0.0107 (5)
C23	0.0704 (11)	0.0616 (10)	0.0617 (10)	−0.0096 (8)	0.0024 (8)	0.0004 (8)

S1—O2	1.4197 (11)	C10—C11	1.377 (2)
S1—O1	1.4208 (11)	C10—H10	0.9300
S1—N1	1.6521 (12)	C11—C12	1.385 (2)
S1—C1	1.7461 (16)	C11—H11	0.9300
O3—C17	1.3641 (17)	C12—C13	1.4475 (18)
O3—C23	1.414 (2)	C13—C14	1.3748 (18)
N1—C22	1.4340 (16)	C13—C22	1.4107 (18)
N1—C7	1.4352 (17)	C14—C15	1.4120 (19)
C1—C2	1.386 (2)	C14—H14	0.9300
C1—C6	1.388 (2)	C15—C20	1.418 (2)
C2—C3	1.385 (3)	C15—C16	1.4219 (19)
C2—H2	0.9300	C16—C17	1.366 (2)
C3—C4	1.386 (3)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.407 (2)
C4—C5	1.369 (3)	C18—C19	1.356 (2)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.368 (3)	C19—C20	1.4200 (19)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—C21	1.4146 (19)
C7—C8	1.3833 (19)	C21—C22	1.3662 (18)
C7—C12	1.3933 (19)	C21—H21	0.9300
C8—C9	1.386 (2)	C23—H23A	0.9600
C8—H8	0.9300	C23—H23B	0.9600
C9—C10	1.381 (2)	C23—H23C	0.9600
C9—H9	0.9300
O2—S1—O1	119.66 (7)	C10—C11—H11	120.6
O2—S1—N1	106.69 (6)	C12—C11—H11	120.6
O1—S1—N1	106.78 (7)	C11—C12—C7	119.86 (13)
O2—S1—C1	109.52 (7)	C11—C12—C13	131.94 (13)
O1—S1—C1	108.60 (8)	C7—C12—C13	108.10 (12)
N1—S1—C1	104.52 (6)	C14—C13—C22	120.69 (12)
C17—O3—C23	117.30 (13)	C14—C13—C12	131.56 (13)
C22—N1—C7	107.12 (10)	C22—C13—C12	107.65 (11)
C22—N1—S1	122.77 (9)	C13—C14—C15	119.27 (13)
C7—N1—S1	122.08 (9)	C13—C14—H14	120.4
C2—C1—C6	121.82 (16)	C15—C14—H14	120.4
C2—C1—S1	119.46 (12)	C14—C15—C20	119.23 (12)
C6—C1—S1	118.64 (13)	C14—C15—C16	120.91 (13)
C3—C2—C1	117.85 (18)	C20—C15—C16	119.81 (13)
C3—C2—H2	121.1	C17—C16—C15	119.97 (14)
C1—C2—H2	121.1	C17—C16—H16	120.0
C2—C3—C4	120.2 (2)	C15—C16—H16	120.0
C2—C3—H3	119.9	O3—C17—C16	125.14 (15)
C4—C3—H3	119.9	O3—C17—C18	114.46 (13)
C5—C4—C3	120.8 (2)	C16—C17—C18	120.40 (14)
C5—C4—H4	119.6	C19—C18—C17	120.70 (14)
C3—C4—H4	119.6	C19—C18—H18	119.6
C6—C5—C4	120.1 (2)	C17—C18—H18	119.6
C6—C5—H5	119.9	C18—C19—C20	121.16 (14)
C4—C5—H5	119.9	C18—C19—H19	119.4
C5—C6—C1	119.11 (19)	C20—C19—H19	119.4
C5—C6—H6	120.4	C21—C20—C15	120.89 (12)
C1—C6—H6	120.4	C21—C20—C19	121.12 (13)
C8—C7—C12	121.66 (13)	C15—C20—C19	117.95 (13)
C8—C7—N1	129.40 (13)	C22—C21—C20	118.05 (13)
C12—C7—N1	108.81 (11)	C22—C21—H21	121.0
C7—C8—C9	117.38 (14)	C20—C21—H21	121.0
C7—C8—H8	121.3	C21—C22—C13	121.87 (12)
C9—C8—H8	121.3	C21—C22—N1	129.70 (12)
C10—C9—C8	121.48 (14)	C13—C22—N1	108.31 (11)
C10—C9—H9	119.3	O3—C23—H23A	109.5
C8—C9—H9	119.3	O3—C23—H23B	109.5
C11—C10—C9	120.74 (15)	H23A—C23—H23B	109.5
C11—C10—H10	119.6	O3—C23—H23C	109.5
C9—C10—H10	119.6	H23A—C23—H23C	109.5
C10—C11—C12	118.87 (14)	H23B—C23—H23C	109.5
O2—S1—N1—C22	41.56 (12)	C11—C12—C13—C14	−0.7 (3)
O1—S1—N1—C22	170.62 (11)	C7—C12—C13—C14	−176.98 (14)
C1—S1—N1—C22	−74.41 (12)	C11—C12—C13—C22	175.59 (15)
O2—S1—N1—C7	−173.68 (10)	C7—C12—C13—C22	−0.70 (15)
O1—S1—N1—C7	−44.62 (12)	C22—C13—C14—C15	−0.6 (2)
C1—S1—N1—C7	70.35 (11)	C12—C13—C14—C15	175.24 (13)
O2—S1—C1—C2	−29.51 (14)	C13—C14—C15—C20	0.2 (2)
O1—S1—C1—C2	−161.84 (12)	C13—C14—C15—C16	−177.31 (13)
N1—S1—C1—C2	84.48 (13)	C14—C15—C16—C17	176.37 (13)
O2—S1—C1—C6	153.51 (12)	C20—C15—C16—C17	−1.2 (2)
O1—S1—C1—C6	21.18 (14)	C23—O3—C17—C16	5.4 (2)
N1—S1—C1—C6	−92.51 (13)	C23—O3—C17—C18	−173.41 (14)
C6—C1—C2—C3	1.9 (2)	C15—C16—C17—O3	−177.59 (14)
S1—C1—C2—C3	−174.97 (13)	C15—C16—C17—C18	1.2 (2)
C1—C2—C3—C4	−0.1 (3)	O3—C17—C18—C19	178.60 (14)
C2—C3—C4—C5	−1.8 (3)	C16—C17—C18—C19	−0.3 (2)
C3—C4—C5—C6	1.9 (3)	C17—C18—C19—C20	−0.6 (2)
C4—C5—C6—C1	−0.1 (3)	C14—C15—C20—C21	0.4 (2)
C2—C1—C6—C5	−1.9 (3)	C16—C15—C20—C21	177.97 (12)
S1—C1—C6—C5	175.06 (14)	C14—C15—C20—C19	−177.30 (12)
C22—N1—C7—C8	−176.94 (14)	C16—C15—C20—C19	0.3 (2)
S1—N1—C7—C8	33.57 (19)	C18—C19—C20—C21	−177.08 (13)
C22—N1—C7—C12	−1.03 (14)	C18—C19—C20—C15	0.6 (2)
S1—N1—C7—C12	−150.52 (10)	C15—C20—C21—C22	−0.6 (2)
C12—C7—C8—C9	−0.2 (2)	C19—C20—C21—C22	177.01 (12)
N1—C7—C8—C9	175.27 (14)	C20—C21—C22—C13	0.2 (2)
C7—C8—C9—C10	−0.3 (3)	C20—C21—C22—N1	−175.36 (12)
C8—C9—C10—C11	0.4 (3)	C14—C13—C22—C21	0.4 (2)
C9—C10—C11—C12	−0.1 (3)	C12—C13—C22—C21	−176.35 (12)
C10—C11—C12—C7	−0.4 (2)	C14—C13—C22—N1	176.82 (12)
C10—C11—C12—C13	−176.35 (15)	C12—C13—C22—N1	0.06 (14)
C8—C7—C12—C11	0.5 (2)	C7—N1—C22—C21	176.62 (13)
N1—C7—C12—C11	−175.75 (13)	S1—N1—C22—C21	−34.15 (19)
C8—C7—C12—C13	177.36 (13)	C7—N1—C22—C13	0.58 (14)
N1—C7—C12—C13	1.07 (15)	S1—N1—C22—C13	149.81 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1	0.93	2.36	2.951 (2)	121
C21—H21···O2	0.93	2.36	2.9460 (18)	121
C6—H6···O1	0.93	2.54	2.906 (2)	104

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1	0.93	2.36	2.951 (2)	121
C21—H21⋯O2	0.93	2.36	2.9460 (18)	121
C6—H6⋯O1	0.93	2.54	2.906 (2)	104