5-Methyl-12-phenyl-sulfonyl-12H-naphtho-[1,2-b]carbazole.

In the title compound, C(27)H(19)NO(2)S, the naphtho-carbazole unit is approximately planar (r.m.s. deviation = 0.002 Å) except for the N atom, which is displaced by 0.122 (1) Å out of the mean plane. The dihedral angle between the naphtho-carbazole mean plane and the phenyl ring of the phenyl-sulfonyl substituent is 83.16 (3)°. An inter-molecular C-H⋯π inter-action involving the phenyl group and the pyrrole ring is observed in the crystal structure.

Related literature

For the biological activity of indole and carbazole derivatives see: Chai et al. (2006 ▶); Rani et al. (2004 ▶); Panwar et al. (2006 ▶); Abele et al. (2003 ▶). For related structures see: Chakkaravarthi et al. (2007 ▶); Liu et al. (2007 ▶).

Experimental

Crystal data

C27H19NO2S

M = 421.49

Triclinic,

a = 9.4527 (3) Å

b = 10.7457 (3) Å

c = 11.5791 (3) Å

α = 115.592 (1)°

β = 93.324 (2)°

γ = 105.206 (2)°

V = 1003.61 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 295 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.946, T max = 0.964

23737 measured reflections

5360 independent reflections

4477 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.120

S = 1.05

5360 reflections

281 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.29 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, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681104949X/bh2396sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104949X/bh2396Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681104949X/bh2396Isup3.cml

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

C27H19NO2S	Z = 2
Mr = 421.49	F(000) = 440
Triclinic, P1	Dx = 1.395 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4527 (3) Å	Cell parameters from 6046 reflections
b = 10.7457 (3) Å	θ = 2.2–29.0°
c = 11.5791 (3) Å	µ = 0.19 mm−1
α = 115.592 (1)°	T = 295 K
β = 93.324 (2)°	Prism, colourless
γ = 105.206 (2)°	0.30 × 0.25 × 0.20 mm
V = 1003.61 (5) Å3

Bruker Kappa APEXII CCD diffractometer	5360 independent reflections
Radiation source: fine-focus sealed tube	4477 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 0 pixels mm-1	θmax = 29.1°, θmin = 2.2°
ω and φ scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→14
Tmin = 0.946, Tmax = 0.964	l = −15→15
23737 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0679P)2 + 0.1767P] where P = (Fo2 + 2Fc2)/3
5360 reflections	(Δ/σ)max < 0.001
281 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.18888 (14)	0.24807 (14)	0.29115 (12)	0.0353 (3)
C2	0.09995 (18)	0.17091 (17)	0.16743 (14)	0.0485 (3)
H2	0.1056	0.0812	0.1079	0.058*
C3	0.0023 (2)	0.2323 (2)	0.13579 (16)	0.0581 (4)
H3	−0.0599	0.1819	0.0538	0.070*
C4	−0.0052 (2)	0.3660 (2)	0.22221 (17)	0.0591 (4)
H4	−0.0720	0.4043	0.1979	0.071*
C5	0.08503 (18)	0.44334 (17)	0.34419 (16)	0.0502 (4)
H5	0.0808	0.5344	0.4020	0.060*
C6	0.18221 (15)	0.38411 (14)	0.37986 (13)	0.0362 (3)
C7	0.28394 (14)	0.43405 (13)	0.50043 (12)	0.0338 (3)
C8	0.35218 (13)	0.32723 (12)	0.48302 (11)	0.0316 (2)
C9	0.45294 (14)	0.34082 (13)	0.58145 (12)	0.0346 (3)
H9	0.4977	0.2694	0.5675	0.042*
C10	0.48713 (14)	0.46487 (13)	0.70383 (12)	0.0331 (3)
C11	0.42165 (15)	0.57442 (13)	0.72159 (12)	0.0363 (3)
C12	0.32029 (15)	0.55734 (14)	0.61848 (13)	0.0389 (3)
H12	0.2776	0.6296	0.6300	0.047*
C13	0.46254 (17)	0.70407 (14)	0.84397 (14)	0.0444 (3)
H13	0.4194	0.7756	0.8538	0.053*
C14	0.56095 (17)	0.72673 (15)	0.94549 (13)	0.0447 (3)
C15	0.62605 (16)	0.61556 (14)	0.93291 (12)	0.0404 (3)
C16	0.59082 (15)	0.48544 (13)	0.81357 (12)	0.0367 (3)
C17	0.65618 (19)	0.38032 (16)	0.80598 (14)	0.0493 (4)
H17	0.6333	0.2943	0.7283	0.059*
C18	0.7536 (2)	0.40075 (19)	0.91058 (16)	0.0605 (4)
H18	0.7960	0.3294	0.9032	0.073*
C19	0.7880 (2)	0.52832 (19)	1.02674 (16)	0.0625 (5)
H19	0.8538	0.5427	1.0976	0.075*
C20	0.7258 (2)	0.63266 (17)	1.03758 (14)	0.0535 (4)
H20	0.7499	0.7176	1.1164	0.064*
C21	0.6035 (2)	0.86763 (18)	1.07059 (16)	0.0640 (5)
H21A	0.5506	0.9292	1.0621	0.096*
H21B	0.7091	0.9158	1.0881	0.096*
H21C	0.5777	0.8477	1.1412	0.096*
C22	0.21436 (14)	−0.03734 (13)	0.37019 (12)	0.0345 (3)
C23	0.27678 (16)	−0.03293 (15)	0.48342 (14)	0.0416 (3)
H23	0.3771	0.0189	0.5212	0.050*
C24	0.18862 (19)	−0.10623 (18)	0.53972 (16)	0.0515 (4)
H24	0.2293	−0.1045	0.6157	0.062*
C25	0.04021 (19)	−0.18190 (17)	0.48296 (17)	0.0540 (4)
H25	−0.0191	−0.2308	0.5214	0.065*
C26	−0.02169 (18)	−0.18632 (17)	0.37012 (17)	0.0535 (4)
H26	−0.1222	−0.2380	0.3329	0.064*
C27	0.06510 (16)	−0.11417 (15)	0.31198 (14)	0.0449 (3)
H27	0.0243	−0.1170	0.2355	0.054*
N1	0.29778 (12)	0.21380 (11)	0.35213 (10)	0.0351 (2)
O1	0.26995 (12)	−0.02036 (11)	0.16013 (9)	0.0458 (2)
O2	0.47830 (10)	0.08335 (10)	0.34758 (9)	0.0414 (2)
S1	0.32587 (3)	0.05452 (3)	0.29722 (3)	0.03372 (10)

	U11	U22	U33	U12	U13	U23
C1	0.0346 (6)	0.0376 (6)	0.0340 (6)	0.0090 (5)	0.0029 (5)	0.0189 (5)
C2	0.0535 (9)	0.0477 (8)	0.0375 (7)	0.0172 (7)	−0.0048 (6)	0.0147 (6)
C3	0.0605 (10)	0.0640 (10)	0.0474 (8)	0.0204 (8)	−0.0091 (7)	0.0258 (8)
C4	0.0613 (10)	0.0668 (10)	0.0589 (10)	0.0291 (8)	−0.0019 (8)	0.0345 (8)
C5	0.0558 (9)	0.0471 (8)	0.0532 (9)	0.0225 (7)	0.0039 (7)	0.0254 (7)
C6	0.0364 (6)	0.0360 (6)	0.0380 (6)	0.0095 (5)	0.0049 (5)	0.0201 (5)
C7	0.0328 (6)	0.0319 (6)	0.0362 (6)	0.0075 (5)	0.0052 (5)	0.0173 (5)
C8	0.0317 (6)	0.0284 (5)	0.0292 (5)	0.0056 (4)	0.0040 (4)	0.0111 (4)
C9	0.0365 (6)	0.0309 (6)	0.0312 (6)	0.0100 (5)	0.0020 (5)	0.0107 (5)
C10	0.0344 (6)	0.0300 (5)	0.0302 (6)	0.0063 (5)	0.0048 (4)	0.0121 (5)
C11	0.0382 (7)	0.0309 (6)	0.0338 (6)	0.0081 (5)	0.0064 (5)	0.0116 (5)
C12	0.0419 (7)	0.0319 (6)	0.0419 (7)	0.0142 (5)	0.0064 (5)	0.0151 (5)
C13	0.0519 (8)	0.0327 (6)	0.0407 (7)	0.0150 (6)	0.0076 (6)	0.0096 (5)
C14	0.0512 (8)	0.0364 (6)	0.0337 (6)	0.0094 (6)	0.0062 (6)	0.0079 (5)
C15	0.0456 (7)	0.0355 (6)	0.0307 (6)	0.0058 (5)	0.0041 (5)	0.0116 (5)
C16	0.0397 (7)	0.0335 (6)	0.0306 (6)	0.0067 (5)	0.0031 (5)	0.0125 (5)
C17	0.0613 (9)	0.0408 (7)	0.0372 (7)	0.0178 (7)	−0.0031 (6)	0.0113 (6)
C18	0.0766 (12)	0.0516 (9)	0.0485 (9)	0.0251 (8)	−0.0101 (8)	0.0191 (7)
C19	0.0790 (12)	0.0561 (9)	0.0422 (8)	0.0184 (8)	−0.0139 (8)	0.0187 (7)
C20	0.0673 (10)	0.0451 (8)	0.0328 (7)	0.0099 (7)	−0.0054 (6)	0.0111 (6)
C21	0.0805 (12)	0.0458 (8)	0.0424 (8)	0.0222 (8)	−0.0008 (8)	0.0005 (7)
C22	0.0339 (6)	0.0299 (5)	0.0355 (6)	0.0112 (5)	0.0042 (5)	0.0114 (5)
C23	0.0374 (7)	0.0442 (7)	0.0436 (7)	0.0138 (6)	0.0035 (5)	0.0208 (6)
C24	0.0567 (9)	0.0550 (8)	0.0525 (9)	0.0209 (7)	0.0130 (7)	0.0315 (7)
C25	0.0565 (9)	0.0440 (8)	0.0647 (10)	0.0143 (7)	0.0239 (8)	0.0276 (7)
C26	0.0391 (8)	0.0444 (8)	0.0594 (9)	0.0033 (6)	0.0065 (7)	0.0150 (7)
C27	0.0390 (7)	0.0409 (7)	0.0434 (7)	0.0080 (6)	−0.0013 (6)	0.0134 (6)
N1	0.0378 (6)	0.0323 (5)	0.0290 (5)	0.0108 (4)	−0.0012 (4)	0.0101 (4)
O1	0.0552 (6)	0.0442 (5)	0.0280 (5)	0.0177 (4)	0.0019 (4)	0.0078 (4)
O2	0.0335 (5)	0.0459 (5)	0.0406 (5)	0.0156 (4)	0.0065 (4)	0.0150 (4)
S1	0.03463 (17)	0.03321 (16)	0.02764 (16)	0.01181 (12)	0.00277 (11)	0.00900 (12)

C1—C2	1.3838 (18)	C15—C16	1.4172 (17)
C1—C6	1.3981 (18)	C16—C17	1.397 (2)
C1—N1	1.4258 (16)	C17—C18	1.378 (2)
C2—C3	1.382 (2)	C17—H17	0.9300
C2—H2	0.9300	C18—C19	1.384 (2)
C3—C4	1.374 (3)	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.361 (2)
C4—C5	1.374 (2)	C19—H19	0.9300
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.3818 (19)	C21—H21A	0.9600
C5—H5	0.9300	C21—H21B	0.9600
C6—C7	1.4451 (17)	C21—H21C	0.9600
C7—C12	1.3725 (17)	C22—C23	1.3825 (18)
C7—C8	1.4063 (17)	C22—C27	1.3872 (18)
C8—C9	1.3729 (16)	C22—S1	1.7542 (13)
C8—N1	1.4255 (14)	C23—C24	1.379 (2)
C9—C10	1.4065 (16)	C23—H23	0.9300
C9—H9	0.9300	C24—C25	1.376 (2)
C10—C11	1.4139 (18)	C24—H24	0.9300
C10—C16	1.4572 (17)	C25—C26	1.377 (2)
C11—C12	1.4010 (18)	C25—H25	0.9300
C11—C13	1.4307 (18)	C26—C27	1.382 (2)
C12—H12	0.9300	C26—H26	0.9300
C13—C14	1.347 (2)	C27—H27	0.9300
C13—H13	0.9300	N1—S1	1.6499 (11)
C14—C15	1.440 (2)	O1—S1	1.4223 (9)
C14—C21	1.5069 (19)	O2—S1	1.4228 (10)
C15—C20	1.406 (2)
C2—C1—C6	121.28 (12)	C15—C16—C10	119.28 (12)
C2—C1—N1	130.60 (12)	C18—C17—C16	121.74 (14)
C6—C1—N1	108.12 (11)	C18—C17—H17	119.1
C3—C2—C1	117.42 (14)	C16—C17—H17	119.1
C3—C2—H2	121.3	C17—C18—C19	119.51 (16)
C1—C2—H2	121.3	C17—C18—H18	120.2
C4—C3—C2	121.79 (15)	C19—C18—H18	120.2
C4—C3—H3	119.1	C20—C19—C18	120.24 (15)
C2—C3—H3	119.1	C20—C19—H19	119.9
C5—C4—C3	120.61 (15)	C18—C19—H19	119.9
C5—C4—H4	119.7	C19—C20—C15	121.79 (14)
C3—C4—H4	119.7	C19—C20—H20	119.1
C4—C5—C6	119.13 (15)	C15—C20—H20	119.1
C4—C5—H5	120.4	C14—C21—H21A	109.5
C6—C5—H5	120.4	C14—C21—H21B	109.5
C5—C6—C1	119.74 (13)	H21A—C21—H21B	109.5
C5—C6—C7	132.16 (13)	C14—C21—H21C	109.5
C1—C6—C7	108.06 (11)	H21A—C21—H21C	109.5
C12—C7—C8	119.46 (11)	H21B—C21—H21C	109.5
C12—C7—C6	132.79 (12)	C23—C22—C27	121.37 (13)
C8—C7—C6	107.75 (11)	C23—C22—S1	119.60 (10)
C9—C8—C7	122.08 (11)	C27—C22—S1	119.03 (10)
C9—C8—N1	129.99 (11)	C24—C23—C22	119.25 (13)
C7—C8—N1	107.94 (10)	C24—C23—H23	120.4
C8—C9—C10	118.68 (12)	C22—C23—H23	120.4
C8—C9—H9	120.7	C25—C24—C23	119.69 (15)
C10—C9—H9	120.7	C25—C24—H24	120.2
C9—C10—C11	119.69 (11)	C23—C24—H24	120.2
C9—C10—C16	121.78 (12)	C24—C25—C26	120.97 (15)
C11—C10—C16	118.52 (11)	C24—C25—H25	119.5
C12—C11—C10	119.97 (12)	C26—C25—H25	119.5
C12—C11—C13	120.35 (12)	C25—C26—C27	120.14 (14)
C10—C11—C13	119.66 (12)	C25—C26—H26	119.9
C7—C12—C11	120.07 (12)	C27—C26—H26	119.9
C7—C12—H12	120.0	C26—C27—C22	118.58 (14)
C11—C12—H12	120.0	C26—C27—H27	120.7
C14—C13—C11	122.69 (14)	C22—C27—H27	120.7
C14—C13—H13	118.7	C8—N1—C1	108.03 (10)
C11—C13—H13	118.7	C8—N1—S1	124.03 (8)
C13—C14—C15	119.35 (12)	C1—N1—S1	126.23 (8)
C13—C14—C21	120.28 (14)	O1—S1—O2	120.40 (6)
C15—C14—C21	120.37 (14)	O1—S1—N1	106.72 (6)
C20—C15—C16	118.27 (14)	O2—S1—N1	106.51 (6)
C20—C15—C14	121.30 (13)	O1—S1—C22	108.78 (6)
C16—C15—C14	120.43 (12)	O2—S1—C22	108.04 (6)
C17—C16—C15	118.46 (12)	N1—S1—C22	105.42 (6)
C17—C16—C10	122.26 (12)
C6—C1—C2—C3	−1.1 (2)	C20—C15—C16—C10	179.69 (13)
N1—C1—C2—C3	179.49 (15)	C14—C15—C16—C10	−0.39 (19)
C1—C2—C3—C4	1.1 (3)	C9—C10—C16—C17	−3.4 (2)
C2—C3—C4—C5	−0.1 (3)	C11—C10—C16—C17	177.57 (13)
C3—C4—C5—C6	−1.0 (3)	C9—C10—C16—C15	177.25 (12)
C4—C5—C6—C1	0.9 (2)	C11—C10—C16—C15	−1.77 (18)
C4—C5—C6—C7	−176.62 (15)	C15—C16—C17—C18	−0.4 (2)
C2—C1—C6—C5	0.1 (2)	C10—C16—C17—C18	−179.74 (15)
N1—C1—C6—C5	179.63 (13)	C16—C17—C18—C19	0.2 (3)
C2—C1—C6—C7	178.23 (13)	C17—C18—C19—C20	0.1 (3)
N1—C1—C6—C7	−2.27 (14)	C18—C19—C20—C15	−0.2 (3)
C5—C6—C7—C12	−1.4 (3)	C16—C15—C20—C19	−0.1 (2)
C1—C6—C7—C12	−179.23 (14)	C14—C15—C20—C19	−179.97 (16)
C5—C6—C7—C8	178.09 (15)	C27—C22—C23—C24	−0.1 (2)
C1—C6—C7—C8	0.31 (14)	S1—C22—C23—C24	−179.57 (11)
C12—C7—C8—C9	1.12 (19)	C22—C23—C24—C25	−0.3 (2)
C6—C7—C8—C9	−178.49 (11)	C23—C24—C25—C26	0.4 (2)
C12—C7—C8—N1	−178.62 (11)	C24—C25—C26—C27	0.0 (3)
C6—C7—C8—N1	1.77 (13)	C25—C26—C27—C22	−0.4 (2)
C7—C8—C9—C10	0.81 (19)	C23—C22—C27—C26	0.5 (2)
N1—C8—C9—C10	−179.52 (12)	S1—C22—C27—C26	179.90 (11)
C8—C9—C10—C11	−2.16 (18)	C9—C8—N1—C1	177.12 (12)
C8—C9—C10—C16	178.83 (11)	C7—C8—N1—C1	−3.17 (13)
C9—C10—C11—C12	1.62 (19)	C9—C8—N1—S1	11.21 (19)
C16—C10—C11—C12	−179.33 (12)	C7—C8—N1—S1	−169.08 (9)
C9—C10—C11—C13	−176.69 (12)	C2—C1—N1—C8	−177.19 (14)
C16—C10—C11—C13	2.35 (19)	C6—C1—N1—C8	3.37 (14)
C8—C7—C12—C11	−1.66 (19)	C2—C1—N1—S1	−11.7 (2)
C6—C7—C12—C11	177.83 (13)	C6—C1—N1—S1	168.89 (9)
C10—C11—C12—C7	0.3 (2)	C8—N1—S1—O1	−173.31 (10)
C13—C11—C12—C7	178.62 (12)	C1—N1—S1—O1	23.37 (13)
C12—C11—C13—C14	−179.06 (14)	C8—N1—S1—O2	−43.51 (11)
C10—C11—C13—C14	−0.7 (2)	C1—N1—S1—O2	153.16 (11)
C11—C13—C14—C15	−1.5 (2)	C8—N1—S1—C22	71.12 (11)
C11—C13—C14—C21	178.00 (14)	C1—N1—S1—C22	−92.20 (11)
C13—C14—C15—C20	−178.06 (15)	C23—C22—S1—O1	150.21 (11)
C21—C14—C15—C20	2.5 (2)	C27—C22—S1—O1	−29.23 (13)
C13—C14—C15—C16	2.0 (2)	C23—C22—S1—O2	17.93 (13)
C21—C14—C15—C16	−177.44 (14)	C27—C22—S1—O2	−161.51 (11)
C20—C15—C16—C17	0.3 (2)	C23—C22—S1—N1	−95.64 (11)
C14—C15—C16—C17	−179.76 (14)	C27—C22—S1—N1	84.91 (11)

Cg1 is the centroid of the pyrrole ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.31	2.9003 (18)	121.
C9—H9···O2	0.93	2.42	2.9994 (15)	120.
C23—H23···O2	0.93	2.55	2.9088 (18)	103.
C25—H25···Cg1i	0.93	2.61	3.4770 (2)	156.

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the pyrrole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25⋯Cg1i	0.93	2.61	3.4770 (2)	156

Symmetry code: (i) .