9-(4-Bromo-but-yl)-9H-carbazole.

In the title compound, C(16)H(16)BrN, the tricyclic carbazole system is essentially planar (r.m.s. deviation of all non-H atoms = 0.010 Å). The dihedral angle between the two outer carbazole rings is 1.1 (3)°. There are no directional inter-molecular contacts in the crystal packing.

Related literature

For synthesis and properties of carbazole derivatives, see: Bo et al. (1998 ▶). For chemical properties of carbazoles, see: Knolker & Reddy (2002 ▶), for their physical properties, see: Koyuncu et al. (2011 ▶), for their medicinal properties, see: Zhang et al. (2010 ▶) and for their opto-electronic and electrochemical properties, see: Taranekar et al. (2007 ▶); Morisaki et al. (2009 ▶). For related structures, see: Gerkin & Reppart (1986 ▶); Duan et al. (2005 ▶); Zhou et al. (2008 ▶); Panchatcharam et al. (2011 ▶).

Experimental

Crystal data

C16H16BrN

M = 302.21

Orthorhombic,

a = 16.0949 (4) Å

b = 7.7012 (2) Å

c = 22.6874 (4) Å

V = 2812.10 (11) Å3

Z = 8

Mo Kα radiation

μ = 2.91 mm−1

T = 293 K

0.24 × 0.21 × 0.17 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.510, T max = 0.589

25173 measured reflections

2860 independent reflections

2002 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.146

S = 1.03

2860 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.45 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022398/zs2201sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022398/zs2201Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022398/zs2201Isup3.cml

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

C16H16BrN	Dx = 1.428 Mg m−3
Mr = 302.21	Melting point: 379(1) K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 18997 reflections
a = 16.0949 (4) Å	θ = 2.9–26.4°
b = 7.7012 (2) Å	µ = 2.91 mm−1
c = 22.6874 (4) Å	T = 293 K
V = 2812.10 (11) Å3	Prism, colourless
Z = 8	0.24 × 0.21 × 0.17 mm
F(000) = 1232

Nonius KappaCCD diffractometer	2860 independent reflections
Radiation source: fine-focus sealed tube	2002 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
CCD rotation images, thick slices scans	θmax = 26.4°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→20
Tmin = 0.510, Tmax = 0.589	k = −9→9
25173 measured reflections	l = −28→19

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.064P)2 + 2.1492P] where P = (Fo2 + 2Fc2)/3
2860 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.45 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
Br	0.35086 (4)	1.17737 (6)	0.51126 (3)	0.1073 (3)
N1	0.43223 (16)	0.4566 (3)	0.63370 (11)	0.0617 (6)
C1	0.5664 (2)	0.4352 (6)	0.57887 (17)	0.0885 (11)
H1	0.5559	0.5272	0.5534	0.106*
C2	0.6389 (3)	0.3424 (9)	0.5758 (2)	0.1156 (19)
H2	0.6783	0.3726	0.5476	0.139*
C3	0.6552 (3)	0.2047 (9)	0.6134 (3)	0.118 (2)
H3	0.7049	0.1442	0.6098	0.141*
C4	0.5985 (3)	0.1559 (6)	0.6562 (2)	0.0960 (14)
H4	0.6096	0.0633	0.6813	0.115*
C5	0.4308 (3)	0.1312 (5)	0.74590 (18)	0.0816 (11)
H5	0.4668	0.0449	0.7589	0.098*
C6	0.3562 (3)	0.1551 (6)	0.7728 (2)	0.0954 (14)
H6	0.3414	0.0846	0.8045	0.115*
C7	0.3019 (3)	0.2824 (5)	0.75390 (18)	0.0859 (11)
H7	0.2510	0.2951	0.7728	0.103*
C8	0.3215 (2)	0.3911 (5)	0.70768 (16)	0.0702 (9)
H8	0.2848	0.4770	0.6953	0.084*
C10	0.5093 (2)	0.3865 (5)	0.62154 (14)	0.0655 (8)
C11	0.5247 (2)	0.2484 (5)	0.66088 (16)	0.0681 (9)
C12	0.4529 (2)	0.2368 (4)	0.69877 (14)	0.0624 (8)
C13	0.39748 (19)	0.3677 (4)	0.68040 (14)	0.0578 (7)
C14	0.3937 (2)	0.6011 (4)	0.60257 (15)	0.0690 (9)
H14A	0.3347	0.5782	0.5985	0.083*
H14B	0.4172	0.6086	0.5633	0.083*
C15	0.4052 (3)	0.7739 (5)	0.63337 (18)	0.0841 (11)
H15A	0.4641	0.8002	0.6356	0.101*
H15B	0.3841	0.7652	0.6733	0.101*
C16	0.3595 (2)	0.9255 (5)	0.60072 (19)	0.0807 (10)
H16A	0.3055	0.8862	0.5872	0.097*
H16B	0.3510	1.0218	0.6277	0.097*
C17	0.4087 (3)	0.9825 (5)	0.55080 (19)	0.0903 (11)
H17A	0.4160	0.8872	0.5233	0.108*
H17B	0.4631	1.0198	0.5641	0.108*

	U11	U22	U33	U12	U13	U23
Br	0.1314 (5)	0.0737 (3)	0.1168 (4)	−0.0018 (2)	−0.0395 (3)	0.0214 (2)
N1	0.0734 (16)	0.0522 (14)	0.0593 (15)	0.0028 (12)	−0.0059 (12)	0.0041 (12)
C1	0.086 (2)	0.113 (3)	0.066 (2)	−0.008 (2)	0.002 (2)	−0.015 (2)
C2	0.083 (3)	0.180 (6)	0.084 (3)	0.001 (3)	0.003 (2)	−0.043 (4)
C3	0.081 (3)	0.167 (6)	0.106 (4)	0.039 (3)	−0.023 (3)	−0.062 (4)
C4	0.090 (3)	0.102 (3)	0.096 (3)	0.032 (2)	−0.035 (3)	−0.031 (2)
C5	0.101 (3)	0.063 (2)	0.081 (2)	−0.009 (2)	−0.031 (2)	0.0146 (18)
C6	0.115 (4)	0.088 (3)	0.083 (3)	−0.033 (3)	−0.014 (3)	0.025 (2)
C7	0.081 (3)	0.095 (3)	0.081 (2)	−0.023 (2)	0.000 (2)	0.006 (2)
C8	0.0662 (19)	0.069 (2)	0.075 (2)	−0.0044 (17)	−0.0103 (17)	0.0006 (18)
C10	0.072 (2)	0.0667 (19)	0.0577 (18)	−0.0047 (16)	−0.0081 (16)	−0.0118 (16)
C11	0.070 (2)	0.0630 (19)	0.071 (2)	0.0079 (17)	−0.0221 (17)	−0.0164 (17)
C12	0.075 (2)	0.0460 (15)	0.0662 (19)	−0.0012 (15)	−0.0232 (16)	−0.0021 (14)
C13	0.0655 (18)	0.0486 (15)	0.0595 (17)	−0.0051 (14)	−0.0124 (15)	−0.0006 (13)
C14	0.086 (2)	0.0568 (18)	0.0639 (19)	−0.0002 (17)	−0.0141 (17)	0.0060 (15)
C15	0.106 (3)	0.066 (2)	0.080 (2)	−0.0028 (19)	−0.013 (2)	−0.0008 (18)
C16	0.079 (2)	0.067 (2)	0.096 (3)	−0.0004 (17)	0.0006 (19)	−0.0061 (19)
C17	0.098 (3)	0.077 (2)	0.095 (3)	−0.003 (2)	−0.010 (2)	0.008 (2)

Br—C17	1.981 (4)	C7—C8	1.378 (5)
N1—C13	1.380 (4)	C7—H7	0.9300
N1—C10	1.380 (4)	C8—C13	1.383 (5)
N1—C14	1.457 (4)	C8—H8	0.9300
C1—C2	1.371 (7)	C10—C11	1.411 (5)
C1—C10	1.387 (5)	C11—C12	1.442 (5)
C1—H1	0.9300	C12—C13	1.409 (4)
C2—C3	1.385 (9)	C14—C15	1.514 (5)
C2—H2	0.9300	C14—H14A	0.9700
C3—C4	1.386 (8)	C14—H14B	0.9700
C3—H3	0.9300	C15—C16	1.567 (5)
C4—C11	1.389 (5)	C15—H15A	0.9700
C4—H4	0.9300	C15—H15B	0.9700
C5—C6	1.360 (6)	C16—C17	1.450 (6)
C5—C12	1.389 (5)	C16—H16A	0.9700
C5—H5	0.9300	C16—H16B	0.9700
C6—C7	1.382 (6)	C17—H17A	0.9700
C6—H6	0.9300	C17—H17B	0.9700
C13—N1—C10	108.9 (3)	C10—C11—C12	106.5 (3)
C13—N1—C14	125.4 (3)	C5—C12—C13	118.9 (4)
C10—N1—C14	125.8 (3)	C5—C12—C11	134.4 (3)
C2—C1—C10	117.3 (5)	C13—C12—C11	106.6 (3)
C2—C1—H1	121.3	N1—C13—C8	129.6 (3)
C10—C1—H1	121.3	N1—C13—C12	109.0 (3)
C1—C2—C3	121.9 (5)	C8—C13—C12	121.4 (3)
C1—C2—H2	119.0	N1—C14—C15	113.3 (3)
C3—C2—H2	119.0	N1—C14—H14A	108.9
C2—C3—C4	121.0 (4)	C15—C14—H14A	108.9
C2—C3—H3	119.5	N1—C14—H14B	108.9
C4—C3—H3	119.5	C15—C14—H14B	108.9
C3—C4—C11	118.5 (5)	H14A—C14—H14B	107.7
C3—C4—H4	120.7	C14—C15—C16	112.3 (3)
C11—C4—H4	120.7	C14—C15—H15A	109.1
C6—C5—C12	119.6 (4)	C16—C15—H15A	109.1
C6—C5—H5	120.2	C14—C15—H15B	109.1
C12—C5—H5	120.2	C16—C15—H15B	109.1
C5—C6—C7	120.9 (4)	H15A—C15—H15B	107.9
C5—C6—H6	119.5	C17—C16—C15	109.7 (3)
C7—C6—H6	119.5	C17—C16—H16A	109.7
C8—C7—C6	121.6 (4)	C15—C16—H16A	109.7
C8—C7—H7	119.2	C17—C16—H16B	109.7
C6—C7—H7	119.2	C15—C16—H16B	109.7
C7—C8—C13	117.6 (3)	H16A—C16—H16B	108.2
C7—C8—H8	121.2	C16—C17—Br	109.0 (3)
C13—C8—H8	121.2	C16—C17—H17A	109.9
N1—C10—C1	129.0 (4)	Br—C17—H17A	109.9
N1—C10—C11	109.0 (3)	C16—C17—H17B	109.9
C1—C10—C11	122.0 (4)	Br—C17—H17B	109.9
C4—C11—C10	119.3 (4)	H17A—C17—H17B	108.3
C4—C11—C12	134.3 (4)
C10—C1—C2—C3	0.2 (7)	C4—C11—C12—C5	1.6 (7)
C1—C2—C3—C4	−0.5 (8)	C10—C11—C12—C5	−179.1 (4)
C2—C3—C4—C11	−0.1 (7)	C4—C11—C12—C13	−179.0 (4)
C12—C5—C6—C7	0.2 (6)	C10—C11—C12—C13	0.3 (3)
C5—C6—C7—C8	−0.7 (7)	C10—N1—C13—C8	−179.7 (3)
C6—C7—C8—C13	0.4 (6)	C14—N1—C13—C8	0.4 (5)
C13—N1—C10—C1	−179.4 (3)	C10—N1—C13—C12	−0.2 (3)
C14—N1—C10—C1	0.5 (5)	C14—N1—C13—C12	179.9 (3)
C13—N1—C10—C11	0.4 (3)	C7—C8—C13—N1	179.9 (3)
C14—N1—C10—C11	−179.7 (3)	C7—C8—C13—C12	0.5 (5)
C2—C1—C10—N1	−179.6 (4)	C5—C12—C13—N1	179.5 (3)
C2—C1—C10—C11	0.6 (5)	C11—C12—C13—N1	0.0 (3)
C3—C4—C11—C10	0.9 (5)	C5—C12—C13—C8	−1.0 (5)
C3—C4—C11—C12	−179.9 (4)	C11—C12—C13—C8	179.5 (3)
N1—C10—C11—C4	178.9 (3)	C13—N1—C14—C15	82.5 (4)
C1—C10—C11—C4	−1.2 (5)	C10—N1—C14—C15	−97.3 (4)
N1—C10—C11—C12	−0.4 (3)	N1—C14—C15—C16	−177.1 (3)
C1—C10—C11—C12	179.4 (3)	C14—C15—C16—C17	−79.7 (4)
C6—C5—C12—C13	0.6 (5)	C15—C16—C17—Br	−178.8 (3)
C6—C5—C12—C11	180.0 (4)