6-Bromo-2-[(E)-thio-phen-2-yl-methyl-idene]-2,3,4,9-tetra-hydro-1H-carbazol-1-one.

In the title compound, C(17)H(12)BrNOS, the cyclo-hexene ring deviates only slightly from planarity (r.m.s. deviation for non-H atoms = 0.047 Å). In the crystal, the mol-ecules are linked into centro-symmetric R(2) (2)(10) dimers via pairs of N-H⋯O hydrogen bonds. The thio-phene ring is disordered over two positions rotated by 180° and with a site-occupation factor of 0.843 (4) for the major occupied site.

Related literature

For the biological activity of carbazole derivatives, see: Magnus et al. (1992 ▶); Abraham (1975 ▶); Saxton (1983 ▶); Phillipson & Zenk (1980 ▶); Bergman & Pelcman (1990 ▶); Bonesi et al. (2004 ▶); Chakraborty et al. (1965 ▶); Kirtikar & Basu (1933 ▶); Chakraborty et al. (1973 ▶); Savini et al. (2004 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Nardelli (1983 ▶). For n class="Chemical">hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H12BrNOS

M = 358.25

Monoclinic,

a = 13.8655 (5) Å

b = 6.3081 (3) Å

c = 17.4583 (7) Å

β = 103.666 (2)°

V = 1483.76 (11) Å3

Z = 4

Mo Kα radiation

μ = 2.91 mm−1

T = 296 K

0.21 × 0.17 × 0.16 mm

Data collection

Bruker SMART APEX CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.558, T max = 0.628

12158 measured reflections

4487 independent reflections

1953 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.148

S = 0.85

4487 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; 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 datablock(s) global, I. DOI: 10.1107/S1600536811046551/bt5684sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046551/bt5684Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811046551/bt5684Isup3.cml

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

C17H12BrNOS	F(000) = 720
Mr = 358.25	Dx = 1.604 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1432 reflections
a = 13.8655 (5) Å	θ = 2.4–30.5°
b = 6.3081 (3) Å	µ = 2.91 mm−1
c = 17.4583 (7) Å	T = 296 K
β = 103.666 (2)°	Block, yellow
V = 1483.76 (11) Å3	0.21 × 0.17 × 0.16 mm
Z = 4

Bruker SMART APEX CCD detector diffractometer	4487 independent reflections
Radiation source: fine-focus sealed tube	1953 reflections with I > 2σ(I)
graphite	Rint = 0.044
ω scans	θmax = 30.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −19→19
Tmin = 0.558, Tmax = 0.628	k = −4→8
12158 measured reflections	l = −24→24

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H-atom parameters constrained
S = 0.85	w = 1/[σ2(Fo2) + (0.0752P)2 + 0.4371P] where P = (Fo2 + 2Fc2)/3
4487 reflections	(Δ/σ)max = 0.002
191 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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	Occ. (<1)
Br1	1.44365 (3)	−0.32770 (7)	0.06412 (3)	0.0742 (2)
S1	0.76193 (8)	−0.1866 (2)	0.24215 (7)	0.0665 (5)	0.843 (4)
C18'	0.76193 (8)	−0.1866 (2)	0.24215 (7)	0.0665 (5)	0.157 (4)
H18'	0.8144	−0.2822	0.2546	0.080*	0.157 (4)
O1	0.91041 (18)	0.3896 (4)	0.06209 (14)	0.0557 (6)
N1	1.1050 (2)	0.2754 (5)	0.04571 (15)	0.0474 (7)
H1	1.0940	0.4036	0.0258	0.057*
C2	1.1893 (2)	0.1612 (5)	0.04737 (18)	0.0419 (8)
C3	1.2698 (3)	0.2105 (6)	0.0147 (2)	0.0546 (10)
H3	1.2722	0.3377	−0.0117	0.066*
C4	1.3444 (3)	0.0657 (7)	0.0229 (2)	0.0569 (10)
H4	1.3992	0.0949	0.0026	0.068*
C5	1.3393 (2)	−0.1272 (6)	0.0619 (2)	0.0523 (9)
C6	1.2619 (2)	−0.1797 (6)	0.09508 (19)	0.0458 (8)
H6	1.2604	−0.3082	0.1209	0.055*
C7	1.1855 (2)	−0.0306 (5)	0.08814 (16)	0.0401 (7)
C8	1.0929 (2)	−0.0273 (5)	0.11198 (16)	0.0380 (7)
C9	1.0491 (3)	−0.1861 (6)	0.1562 (2)	0.0556 (10)
H9A	1.0982	−0.2242	0.2037	0.067*
H9B	1.0334	−0.3129	0.1243	0.067*
C10	0.9568 (3)	−0.1110 (6)	0.1789 (2)	0.0598 (10)
H10A	0.9104	−0.2286	0.1706	0.072*
H10B	0.9746	−0.0836	0.2352	0.072*
C11	0.9014 (2)	0.0798 (5)	0.14016 (17)	0.0405 (7)
C12	0.9501 (2)	0.2235 (6)	0.09254 (18)	0.0413 (8)
C13	1.0475 (2)	0.1591 (5)	0.08458 (17)	0.0412 (8)
C14	0.8096 (2)	0.1348 (6)	0.14535 (19)	0.0472 (8)
H14	0.7854	0.2568	0.1174	0.057*
C15	0.7412 (2)	0.0388 (6)	0.18652 (17)	0.0480 (9)
C16	0.6513 (3)	−0.1697 (8)	0.2658 (2)	0.0711 (13)
H16	0.6297	−0.2663	0.2984	0.085*
C17	0.5980 (3)	−0.0032 (9)	0.2330 (3)	0.0820 (14)
H17	0.5350	0.0233	0.2406	0.098*
S1'	0.6432 (3)	0.1340 (6)	0.1851 (2)	0.0920 (14)	0.157 (4)
C18	0.6432 (3)	0.1340 (6)	0.1851 (2)	0.0920 (14)	0.843 (4)
H18	0.6164	0.2565	0.1589	0.110*	0.843 (4)

	U11	U22	U33	U12	U13	U23
Br1	0.0607 (3)	0.0682 (3)	0.1064 (4)	−0.0012 (2)	0.0451 (2)	−0.0058 (2)
S1	0.0530 (7)	0.0737 (10)	0.0782 (8)	−0.0023 (6)	0.0263 (6)	0.0248 (7)
C18'	0.0530 (7)	0.0737 (10)	0.0782 (8)	−0.0023 (6)	0.0263 (6)	0.0248 (7)
O1	0.0592 (14)	0.0422 (14)	0.0678 (15)	0.0038 (13)	0.0193 (12)	0.0176 (13)
N1	0.0558 (17)	0.0388 (16)	0.0505 (16)	−0.0049 (14)	0.0180 (13)	0.0134 (14)
C2	0.0544 (18)	0.0353 (18)	0.0381 (16)	−0.0101 (17)	0.0152 (14)	0.0008 (15)
C3	0.064 (2)	0.053 (2)	0.0515 (19)	−0.019 (2)	0.0240 (17)	0.0035 (18)
C4	0.058 (2)	0.064 (3)	0.057 (2)	−0.017 (2)	0.0289 (17)	−0.003 (2)
C5	0.0466 (18)	0.057 (2)	0.057 (2)	−0.0071 (18)	0.0210 (16)	−0.0063 (19)
C6	0.0471 (18)	0.044 (2)	0.0508 (18)	−0.0068 (17)	0.0199 (15)	0.0014 (17)
C7	0.0489 (17)	0.0386 (19)	0.0349 (15)	−0.0072 (16)	0.0141 (14)	−0.0016 (15)
C8	0.0455 (16)	0.0348 (18)	0.0352 (15)	−0.0046 (15)	0.0127 (13)	0.0018 (15)
C9	0.054 (2)	0.049 (2)	0.071 (2)	0.0043 (18)	0.0288 (18)	0.0206 (19)
C10	0.066 (2)	0.054 (2)	0.071 (2)	0.009 (2)	0.0374 (19)	0.023 (2)
C11	0.0510 (18)	0.0354 (18)	0.0364 (15)	−0.0037 (16)	0.0129 (14)	−0.0020 (15)
C12	0.0490 (18)	0.0353 (19)	0.0395 (16)	−0.0046 (16)	0.0099 (14)	−0.0004 (16)
C13	0.0471 (17)	0.0367 (19)	0.0408 (16)	−0.0073 (16)	0.0122 (14)	0.0006 (16)
C14	0.0522 (19)	0.044 (2)	0.0455 (18)	−0.0011 (17)	0.0112 (15)	0.0072 (16)
C15	0.0454 (17)	0.059 (2)	0.0402 (16)	−0.0049 (18)	0.0108 (14)	0.0017 (17)
C16	0.052 (2)	0.093 (4)	0.073 (3)	−0.014 (2)	0.022 (2)	0.016 (3)
C17	0.056 (2)	0.117 (4)	0.079 (3)	0.004 (3)	0.027 (2)	0.005 (3)
S1'	0.084 (2)	0.106 (3)	0.093 (2)	−0.006 (2)	0.0363 (18)	0.011 (2)
C18	0.084 (2)	0.106 (3)	0.093 (2)	−0.006 (2)	0.0363 (18)	0.011 (2)

Br1—C5	1.915 (4)	C8—C9	1.480 (4)
S1—C16	1.683 (4)	C9—C10	1.503 (4)
S1—C15	1.707 (4)	C9—H9A	0.9700
O1—C12	1.243 (4)	C9—H9B	0.9700
N1—C2	1.368 (4)	C10—C11	1.500 (5)
N1—C13	1.375 (4)	C10—H10A	0.9700
N1—H1	0.8789	C10—H10B	0.9700
C2—C3	1.403 (4)	C11—C14	1.343 (4)
C2—C7	1.411 (4)	C11—C12	1.495 (4)
C3—C4	1.361 (5)	C12—C13	1.448 (4)
C3—H3	0.9300	C14—C15	1.451 (4)
C4—C5	1.403 (5)	C14—H14	0.9300
C4—H4	0.9300	C15—S1'	1.480 (4)
C5—C6	1.376 (4)	C16—C17	1.333 (6)
C6—C7	1.400 (4)	C16—H16	0.9300
C6—H6	0.9300	C17—S1'	1.445 (6)
C7—C8	1.441 (4)	C17—H17	0.9300
C8—C13	1.366 (4)
C16—S1—C15	92.6 (2)	H9A—C9—H9B	107.7
C2—N1—C13	107.5 (3)	C11—C10—C9	120.7 (3)
C2—N1—H1	124.1	C11—C10—H10A	107.1
C13—N1—H1	128.2	C9—C10—H10A	107.1
N1—C2—C3	129.2 (3)	C11—C10—H10B	107.1
N1—C2—C7	109.2 (3)	C9—C10—H10B	107.1
C3—C2—C7	121.5 (3)	H10A—C10—H10B	106.8
C4—C3—C2	117.7 (3)	C14—C11—C12	116.2 (3)
C4—C3—H3	121.1	C14—C11—C10	124.7 (3)
C2—C3—H3	121.1	C12—C11—C10	119.1 (3)
C3—C4—C5	120.6 (3)	O1—C12—C13	121.6 (3)
C3—C4—H4	119.7	O1—C12—C11	122.5 (3)
C5—C4—H4	119.7	C13—C12—C11	115.9 (3)
C6—C5—C4	123.1 (3)	C8—C13—N1	111.1 (3)
C6—C5—Br1	119.5 (3)	C8—C13—C12	124.8 (3)
C4—C5—Br1	117.3 (2)	N1—C13—C12	124.1 (3)
C5—C6—C7	116.8 (3)	C11—C14—C15	131.8 (3)
C5—C6—H6	121.6	C11—C14—H14	114.1
C7—C6—H6	121.6	C15—C14—H14	114.1
C6—C7—C2	120.1 (3)	C14—C15—S1'	121.8 (3)
C6—C7—C8	133.8 (3)	C14—C15—S1	126.0 (3)
C2—C7—C8	106.0 (3)	S1'—C15—S1	112.2 (2)
C13—C8—C7	106.3 (3)	C17—C16—S1	112.9 (3)
C13—C8—C9	123.6 (3)	C17—C16—H16	123.6
C7—C8—C9	130.1 (3)	S1—C16—H16	123.6
C8—C9—C10	113.8 (3)	C16—C17—S1'	116.6 (4)
C8—C9—H9A	108.8	C16—C17—H17	121.7
C10—C9—H9A	108.8	S1'—C17—H17	121.7
C8—C9—H9B	108.8	C17—S1'—C15	105.6 (3)
C10—C9—H9B	108.8
C13—N1—C2—C3	178.8 (3)	C10—C11—C12—O1	−176.4 (3)
C13—N1—C2—C7	−0.2 (3)	C14—C11—C12—C13	−177.7 (3)
N1—C2—C3—C4	−178.3 (3)	C10—C11—C12—C13	2.9 (4)
C7—C2—C3—C4	0.6 (5)	C7—C8—C13—N1	−0.6 (3)
C2—C3—C4—C5	1.0 (5)	C9—C8—C13—N1	−180.0 (3)
C3—C4—C5—C6	−1.5 (6)	C7—C8—C13—C12	177.2 (3)
C3—C4—C5—Br1	175.9 (3)	C9—C8—C13—C12	−2.2 (5)
C4—C5—C6—C7	0.4 (5)	C2—N1—C13—C8	0.5 (4)
Br1—C5—C6—C7	−176.9 (2)	C2—N1—C13—C12	−177.4 (3)
C5—C6—C7—C2	1.1 (5)	O1—C12—C13—C8	−175.6 (3)
C5—C6—C7—C8	177.9 (3)	C11—C12—C13—C8	5.2 (4)
N1—C2—C7—C6	177.4 (3)	O1—C12—C13—N1	2.0 (5)
C3—C2—C7—C6	−1.6 (5)	C11—C12—C13—N1	−177.3 (3)
N1—C2—C7—C8	−0.2 (3)	C12—C11—C14—C15	−178.8 (3)
C3—C2—C7—C8	−179.3 (3)	C10—C11—C14—C15	0.6 (6)
C6—C7—C8—C13	−176.7 (3)	C11—C14—C15—S1'	178.2 (4)
C2—C7—C8—C13	0.5 (3)	C11—C14—C15—S1	−0.6 (6)
C6—C7—C8—C9	2.7 (6)	C16—S1—C15—C14	178.6 (3)
C2—C7—C8—C9	179.8 (3)	C16—S1—C15—S1'	−0.4 (3)
C13—C8—C9—C10	−8.5 (5)	C15—S1—C16—C17	0.8 (4)
C7—C8—C9—C10	172.2 (3)	S1—C16—C17—S1'	−1.1 (6)
C8—C9—C10—C11	16.1 (5)	C16—C17—S1'—C15	0.8 (5)
C9—C10—C11—C14	166.8 (4)	C14—C15—S1'—C17	−179.2 (3)
C9—C10—C11—C12	−13.8 (5)	S1—C15—S1'—C17	−0.2 (4)
C14—C11—C12—O1	3.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1	0.93	2.33	2.759 (4)	108.
N1—H1···O1i	0.88	2.00	2.804 (4)	151.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88	2.00	2.804 (4)	151

Symmetry code: (i) .