2,3,6,7-Tetra-bromo-9-butyl-9H-carbazole.

In he title compound, C(16)H(13)Br(4)N, the carbazole skeleton is nearly planar [maximum deviation = 0.026 (4) Å] and makes a dihedral angle of 73.8 (4)° with the butyl chain. The butyl chain adopts a trans conformation. In the crystal, mol-ecules are linked by π-π stacking inter-actions [centroid-centroid distance = 3.559 (2) Å].

Related literature

For general background to carbazole derivatives, see: Uludağ et al. (2011 ▶); Zuluaga et al. (2011 ▶). For their biological activity, see: Kubicki et al. (2007 ▶); Lohier et al. (2010 ▶) and for their applications, see: Thomas et al. (2001 ▶); Tsuboyama et al. (2003 ▶). For related structures, see: Ergün et al. (2010 ▶); Saeed et al. (2010 ▶); Chen et al. (2009 ▶); Gagnon & Laliberté (2008 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H13Br4N

M = 538.91

Triclinic,

a = 8.7127 (4) Å

b = 9.5712 (4) Å

c = 11.3379 (5) Å

α = 87.225 (2)°

β = 72.014 (2)°

γ = 67.673 (2)°

V = 829.30 (6) Å3

Z = 2

Mo Kα radiation

μ = 9.70 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.159, T max = 0.247

18599 measured reflections

3816 independent reflections

2739 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.092

S = 1.05

3816 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −1.03 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812013761/bx2400sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013761/bx2400Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812013761/bx2400Isup3.cml

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

C16H13Br4N	Z = 2
Mr = 538.91	F(000) = 512
Triclinic, P1	Dx = 2.158 Mg m−3
a = 8.7127 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.5712 (4) Å	Cell parameters from 3816 reflections
c = 11.3379 (5) Å	θ = 2.3–27.5°
α = 87.225 (2)°	µ = 9.70 mm−1
β = 72.014 (2)°	T = 293 K
γ = 67.673 (2)°	Block, colourless
V = 829.30 (6) Å3	0.30 × 0.25 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	3816 independent reflections
Radiation source: fine-focus sealed tube	2739 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
ω and φ scan	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
Tmin = 0.159, Tmax = 0.247	k = −12→12
18599 measured reflections	l = −14→14

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0467P)2 + 0.1503P] where P = (Fo2 + 2Fc2)/3
3816 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −1.03 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
C11	−0.0404 (4)	0.8421 (4)	−0.2274 (3)	0.0339 (8)
C13	0.2397 (4)	0.2502 (4)	−0.2560 (3)	0.0367 (9)
H13A	0.1541	0.2705	−0.2992	0.044*
H13B	0.2257	0.1748	−0.1979	0.044*
C14	0.4196 (5)	0.1866 (4)	−0.3490 (3)	0.0399 (9)
H14A	0.4358	0.0914	−0.3874	0.048*
H14B	0.5046	0.1647	−0.3051	0.048*
C15	0.4566 (5)	0.2883 (4)	−0.4502 (4)	0.0399 (9)
H15A	0.3721	0.3101	−0.4946	0.048*
H15B	0.4406	0.3836	−0.4121	0.048*
C16	0.6373 (6)	0.2225 (5)	−0.5420 (4)	0.0609 (12)
H16A	0.6519	0.2930	−0.6034	0.091*
H16B	0.6535	0.1295	−0.5819	0.091*
H16C	0.7221	0.2030	−0.4993	0.091*
Br4	−0.14241 (6)	1.05229 (4)	−0.23930 (4)	0.05545 (15)
C1	0.2321 (4)	0.5848 (4)	0.0618 (3)	0.0327 (8)
H1	0.1932	0.6854	0.0910	0.039*
C2	0.3235 (4)	0.4702 (4)	0.1212 (3)	0.0335 (8)
C3	0.3859 (4)	0.3180 (4)	0.0743 (3)	0.0352 (8)
C4	0.3534 (4)	0.2801 (4)	−0.0269 (3)	0.0322 (8)
H4	0.3945	0.1794	−0.0565	0.039*
C5	0.2565 (4)	0.3966 (4)	−0.0850 (3)	0.0291 (8)
C6	0.1984 (4)	0.5490 (4)	−0.0424 (3)	0.0301 (8)
C7	0.1094 (4)	0.6384 (3)	−0.1249 (3)	0.0293 (7)
C8	0.1159 (4)	0.5363 (4)	−0.2117 (3)	0.0296 (8)
C9	0.0450 (4)	0.5845 (4)	−0.3070 (3)	0.0320 (8)
H9	0.0498	0.5156	−0.3644	0.038*
C10	−0.0330 (4)	0.7382 (4)	−0.3138 (3)	0.0329 (8)
C12	0.0301 (4)	0.7926 (4)	−0.1317 (3)	0.0341 (8)
H12	0.0241	0.8614	−0.0735	0.041*
N	0.2045 (4)	0.3899 (3)	−0.1862 (3)	0.0329 (7)
Br1	0.35722 (6)	0.52290 (5)	0.26623 (4)	0.05058 (14)
Br2	−0.11763 (6)	0.80537 (5)	−0.44827 (4)	0.05302 (15)
Br3	0.52215 (6)	0.16149 (5)	0.15025 (4)	0.05527 (15)

	U11	U22	U33	U12	U13	U23
C11	0.0365 (19)	0.0273 (17)	0.035 (2)	−0.0103 (14)	−0.0101 (17)	0.0067 (15)
C13	0.048 (2)	0.0304 (18)	0.035 (2)	−0.0173 (16)	−0.0147 (18)	0.0008 (16)
C14	0.051 (2)	0.0328 (19)	0.034 (2)	−0.0114 (16)	−0.0158 (18)	−0.0008 (16)
C15	0.042 (2)	0.045 (2)	0.035 (2)	−0.0163 (16)	−0.0166 (18)	0.0065 (17)
C16	0.050 (3)	0.080 (3)	0.045 (3)	−0.022 (2)	−0.009 (2)	0.005 (2)
Br4	0.0757 (3)	0.0309 (2)	0.0614 (3)	−0.01020 (19)	−0.0373 (2)	0.00839 (19)
C1	0.0383 (19)	0.0312 (18)	0.028 (2)	−0.0129 (15)	−0.0097 (16)	0.0024 (15)
C2	0.0368 (19)	0.043 (2)	0.024 (2)	−0.0184 (15)	−0.0104 (16)	0.0041 (16)
C3	0.039 (2)	0.0337 (19)	0.033 (2)	−0.0146 (15)	−0.0119 (17)	0.0107 (16)
C4	0.0382 (19)	0.0265 (17)	0.030 (2)	−0.0112 (14)	−0.0104 (16)	0.0064 (15)
C5	0.0330 (18)	0.0304 (17)	0.024 (2)	−0.0150 (14)	−0.0054 (15)	0.0014 (14)
C6	0.0320 (18)	0.0294 (17)	0.027 (2)	−0.0111 (13)	−0.0071 (15)	0.0046 (14)
C7	0.0314 (18)	0.0302 (17)	0.025 (2)	−0.0108 (14)	−0.0083 (15)	0.0050 (15)
C8	0.0307 (18)	0.0315 (17)	0.026 (2)	−0.0140 (14)	−0.0061 (15)	0.0039 (15)
C9	0.0376 (19)	0.0355 (19)	0.025 (2)	−0.0147 (15)	−0.0113 (16)	0.0007 (15)
C10	0.0319 (18)	0.041 (2)	0.025 (2)	−0.0122 (15)	−0.0118 (15)	0.0089 (16)
C12	0.0388 (19)	0.0325 (18)	0.029 (2)	−0.0122 (15)	−0.0100 (17)	0.0018 (15)
N	0.0401 (16)	0.0292 (15)	0.0285 (18)	−0.0110 (12)	−0.0124 (14)	0.0014 (12)
Br1	0.0693 (3)	0.0567 (3)	0.0358 (3)	−0.0256 (2)	−0.0287 (2)	0.00626 (19)
Br2	0.0665 (3)	0.0530 (3)	0.0447 (3)	−0.0154 (2)	−0.0350 (2)	0.0109 (2)
Br3	0.0703 (3)	0.0449 (2)	0.0528 (3)	−0.0126 (2)	−0.0362 (2)	0.0171 (2)

C11—C12	1.386 (5)	C1—H1	0.9300
C11—C10	1.400 (5)	C2—C3	1.413 (5)
C11—Br4	1.883 (3)	C2—Br1	1.880 (4)
C13—N	1.466 (4)	C3—C4	1.359 (5)
C13—C14	1.502 (5)	C3—Br3	1.884 (3)
C13—H13A	0.9700	C4—C5	1.396 (5)
C13—H13B	0.9700	C4—H4	0.9300
C14—C15	1.507 (5)	C5—N	1.370 (4)
C14—H14A	0.9700	C5—C6	1.405 (4)
C14—H14B	0.9700	C6—C7	1.440 (5)
C15—C16	1.502 (5)	C7—C12	1.382 (5)
C15—H15A	0.9700	C7—C8	1.394 (5)
C15—H15B	0.9700	C8—C9	1.381 (5)
C16—H16A	0.9600	C8—N	1.386 (4)
C16—H16B	0.9600	C9—C10	1.376 (5)
C16—H16C	0.9600	C9—H9	0.9300
C1—C2	1.374 (5)	C10—Br2	1.876 (4)
C1—C6	1.389 (5)	C12—H12	0.9300
C12—C11—C10	120.7 (3)	C3—C2—Br1	122.0 (3)
C12—C11—Br4	118.2 (3)	C4—C3—C2	121.8 (3)
C10—C11—Br4	121.1 (3)	C4—C3—Br3	118.2 (3)
N—C13—C14	113.3 (3)	C2—C3—Br3	120.0 (3)
N—C13—H13A	108.9	C3—C4—C5	118.1 (3)
C14—C13—H13A	108.9	C3—C4—H4	121.0
N—C13—H13B	108.9	C5—C4—H4	121.0
C14—C13—H13B	108.9	N—C5—C4	129.9 (3)
H13A—C13—H13B	107.7	N—C5—C6	109.0 (3)
C13—C14—C15	114.9 (3)	C4—C5—C6	121.0 (3)
C13—C14—H14A	108.6	C1—C6—C5	119.8 (3)
C15—C14—H14A	108.6	C1—C6—C7	133.6 (3)
C13—C14—H14B	108.6	C5—C6—C7	106.6 (3)
C15—C14—H14B	108.6	C12—C7—C8	120.4 (3)
H14A—C14—H14B	107.5	C12—C7—C6	133.1 (3)
C16—C15—C14	113.9 (3)	C8—C7—C6	106.5 (3)
C16—C15—H15A	108.8	C9—C8—N	129.0 (3)
C14—C15—H15A	108.8	C9—C8—C7	121.8 (3)
C16—C15—H15B	108.8	N—C8—C7	109.2 (3)
C14—C15—H15B	108.8	C10—C9—C8	117.6 (3)
H15A—C15—H15B	107.7	C10—C9—H9	121.2
C15—C16—H16A	109.5	C8—C9—H9	121.2
C15—C16—H16B	109.5	C9—C10—C11	121.3 (3)
H16A—C16—H16B	109.5	C9—C10—Br2	118.1 (3)
C15—C16—H16C	109.5	C11—C10—Br2	120.6 (3)
H16A—C16—H16C	109.5	C7—C12—C11	118.2 (3)
H16B—C16—H16C	109.5	C7—C12—H12	120.9
C2—C1—C6	119.4 (3)	C11—C12—H12	120.9
C2—C1—H1	120.3	C5—N—C8	108.6 (3)
C6—C1—H1	120.3	C5—N—C13	125.1 (3)
C1—C2—C3	119.9 (3)	C8—N—C13	126.2 (3)
C1—C2—Br1	118.0 (3)
N—C13—C14—C15	−62.0 (4)	C12—C7—C8—N	178.9 (3)
C13—C14—C15—C16	179.9 (3)	C6—C7—C8—N	−0.2 (4)
C6—C1—C2—C3	1.6 (5)	N—C8—C9—C10	−178.2 (3)
C6—C1—C2—Br1	−177.2 (2)	C7—C8—C9—C10	0.1 (5)
C1—C2—C3—C4	−2.2 (5)	C8—C9—C10—C11	0.0 (5)
Br1—C2—C3—C4	176.5 (3)	C8—C9—C10—Br2	176.4 (3)
C1—C2—C3—Br3	176.5 (3)	C12—C11—C10—C9	−0.4 (5)
Br1—C2—C3—Br3	−4.7 (4)	Br4—C11—C10—C9	178.5 (3)
C2—C3—C4—C5	0.5 (5)	C12—C11—C10—Br2	−176.7 (3)
Br3—C3—C4—C5	−178.3 (2)	Br4—C11—C10—Br2	2.3 (4)
C3—C4—C5—N	−179.3 (3)	C8—C7—C12—C11	−0.7 (5)
C3—C4—C5—C6	1.7 (5)	C6—C7—C12—C11	178.0 (4)
C2—C1—C6—C5	0.6 (5)	C10—C11—C12—C7	0.8 (5)
C2—C1—C6—C7	−179.7 (4)	Br4—C11—C12—C7	−178.2 (2)
N—C5—C6—C1	178.6 (3)	C4—C5—N—C8	−177.9 (3)
C4—C5—C6—C1	−2.3 (5)	C6—C5—N—C8	1.1 (4)
N—C5—C6—C7	−1.2 (4)	C4—C5—N—C13	1.3 (6)
C4—C5—C6—C7	177.9 (3)	C6—C5—N—C13	−179.6 (3)
C1—C6—C7—C12	2.2 (7)	C9—C8—N—C5	177.8 (3)
C5—C6—C7—C12	−178.0 (4)	C7—C8—N—C5	−0.6 (4)
C1—C6—C7—C8	−178.9 (4)	C9—C8—N—C13	−1.4 (6)
C5—C6—C7—C8	0.8 (4)	C7—C8—N—C13	−179.8 (3)
C12—C7—C8—C9	0.3 (5)	C14—C13—N—C5	−81.3 (4)
C6—C7—C8—C9	−178.7 (3)	C14—C13—N—C8	97.8 (4)