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

In the title compound, C(16)H(16)BrN, the bromo-butyl group lies on one side of the carbazole ring plane and has a zigzag shape. The dihedral angle between the two benzene rings is 0.55°. In the crystal, mol-ecules are connected by van der Waals inter-actions.

Related literature

For charge-transport properties and π-conjugated systems in carbazoles, see: Zhang et al. (2010a ▶). For the bioactivity of carbazole derivatives, see: Yan et al. (2011 ▶). For the synthesis of the title compound, see: Zhang et al. (2010b ▶).

Experimental

Crystal data

C16H16BrN

M = 302.20

Orthorhombic,

a = 7.696 (3) Å

b = 22.658 (8) Å

c = 16.030 (6) Å

V = 2795.3 (18) Å3

Z = 8

Mo Kα radiation

μ = 2.92 mm−1

T = 296 K

0.35 × 0.33 × 0.32 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.428, T max = 0.455

13981 measured reflections

2460 independent reflections

1252 reflections with I > 2σ(I)

R int = 0.094

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.145

S = 0.97

2460 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.42 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812010987/rk2343sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010987/rk2343Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812010987/rk2343Isup3.cml

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

C16H16BrN	F(000) = 1232
Mr = 302.20	Dx = 1.436 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1683 reflections
a = 7.696 (3) Å	θ = 2.2–20.5°
b = 22.658 (8) Å	µ = 2.92 mm−1
c = 16.030 (6) Å	T = 296 K
V = 2795.3 (18) Å3	Block, colourless
Z = 8	0.35 × 0.33 × 0.32 mm

Bruker SMART CCD diffractometer	2460 independent reflections
Radiation source: fine-focus sealed tube	1252 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.094
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.428, Tmax = 0.455	k = −26→23
13981 measured reflections	l = −19→18

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0728P)2] where P = (Fo2 + 2Fc2)/3
2460 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.42 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
Br1	1.17750 (8)	0.51102 (3)	0.14901 (4)	0.0961 (4)
N1	0.4563 (4)	0.63416 (15)	0.0682 (2)	0.0503 (9)
C1	0.9838 (6)	0.5506 (2)	0.0916 (3)	0.0804 (16)
H1A	1.0214	0.5640	0.0371	0.097*
H1B	0.8887	0.5230	0.0840	0.097*
C2	0.9256 (7)	0.6005 (2)	0.1406 (3)	0.0728 (15)
H2A	1.0216	0.6275	0.1495	0.087*
H2B	0.8853	0.5869	0.1946	0.087*
C3	0.7738 (6)	0.6334 (2)	0.0939 (3)	0.0710 (16)
H3A	0.7660	0.6736	0.1143	0.085*
H3B	0.7995	0.6349	0.0347	0.085*
C4	0.6020 (6)	0.60279 (19)	0.1069 (3)	0.0589 (12)
H4A	0.6086	0.5633	0.0837	0.071*
H4B	0.5804	0.5991	0.1662	0.071*
C5	0.3858 (6)	0.6217 (2)	−0.0087 (3)	0.0534 (12)
C6	0.4334 (8)	0.5788 (2)	−0.0656 (3)	0.0744 (15)
H6	0.5249	0.5531	−0.0549	0.089*
C7	0.3397 (11)	0.5757 (3)	−0.1393 (4)	0.107 (2)
H7	0.3692	0.5475	−0.1791	0.128*
C8	0.2017 (10)	0.6140 (4)	−0.1546 (4)	0.106 (3)
H8	0.1403	0.6107	−0.2044	0.127*
C9	0.1550 (7)	0.6562 (3)	−0.0986 (4)	0.0820 (17)
H9	0.0626	0.6815	−0.1095	0.098*
C10	0.2482 (6)	0.6607 (2)	−0.0248 (3)	0.0546 (12)
C11	0.2370 (5)	0.6987 (2)	0.0468 (3)	0.0517 (12)
C12	0.1309 (6)	0.7458 (2)	0.0690 (4)	0.0684 (15)
H12	0.0438	0.7587	0.0331	0.082*
C13	0.1557 (7)	0.7729 (3)	0.1436 (4)	0.0810 (17)
H13	0.0852	0.8046	0.1584	0.097*
C14	0.2847 (7)	0.7542 (2)	0.1985 (4)	0.0744 (16)
H14	0.2990	0.7734	0.2493	0.089*
C15	0.3906 (6)	0.7079 (2)	0.1782 (3)	0.0576 (12)
H15	0.4762	0.6952	0.2150	0.069*
C16	0.3682 (5)	0.68078 (19)	0.1028 (3)	0.0462 (11)

	U11	U22	U33	U12	U13	U23
Br1	0.0657 (4)	0.1089 (6)	0.1138 (6)	0.0220 (3)	0.0026 (3)	0.0376 (4)
N1	0.046 (2)	0.051 (2)	0.054 (3)	0.0042 (18)	−0.0053 (18)	0.0027 (19)
C1	0.068 (4)	0.086 (4)	0.087 (4)	0.003 (3)	0.000 (3)	0.013 (3)
C2	0.062 (3)	0.089 (4)	0.068 (4)	−0.010 (3)	0.001 (3)	−0.007 (3)
C3	0.049 (3)	0.070 (3)	0.094 (5)	0.004 (2)	0.000 (3)	0.017 (3)
C4	0.046 (3)	0.059 (3)	0.072 (3)	0.006 (2)	−0.002 (3)	0.011 (3)
C5	0.055 (3)	0.047 (3)	0.058 (3)	−0.011 (2)	0.008 (3)	0.006 (3)
C6	0.101 (4)	0.060 (3)	0.062 (4)	−0.010 (3)	0.003 (3)	0.004 (3)
C7	0.171 (8)	0.082 (5)	0.067 (5)	−0.049 (5)	0.010 (5)	−0.003 (4)
C8	0.151 (7)	0.095 (5)	0.072 (5)	−0.050 (5)	−0.043 (5)	0.022 (4)
C9	0.090 (4)	0.085 (4)	0.071 (4)	−0.030 (3)	−0.028 (4)	0.031 (4)
C10	0.050 (3)	0.060 (3)	0.054 (4)	−0.014 (2)	−0.003 (2)	0.015 (3)
C11	0.036 (2)	0.056 (3)	0.063 (4)	−0.002 (2)	0.003 (2)	0.024 (3)
C12	0.053 (3)	0.074 (4)	0.079 (4)	0.011 (3)	0.007 (3)	0.028 (3)
C13	0.075 (4)	0.071 (4)	0.097 (5)	0.020 (3)	0.030 (4)	0.013 (4)
C14	0.087 (4)	0.077 (4)	0.060 (4)	0.007 (3)	0.018 (3)	0.004 (3)
C15	0.056 (3)	0.067 (3)	0.050 (3)	0.003 (3)	0.003 (2)	0.009 (3)
C16	0.043 (3)	0.049 (3)	0.046 (3)	−0.002 (2)	0.006 (2)	0.010 (2)

Br1—C1	1.968 (5)	C6—H6	0.9300
N1—C16	1.372 (5)	C7—C8	1.394 (10)
N1—C5	1.377 (5)	C7—H7	0.9300
N1—C4	1.465 (5)	C8—C9	1.361 (9)
C1—C2	1.447 (7)	C8—H8	0.9300
C1—H1A	0.9700	C9—C10	1.386 (7)
C1—H1B	0.9700	C9—H9	0.9300
C2—C3	1.575 (6)	C10—C11	1.437 (7)
C2—H2A	0.9700	C11—C12	1.391 (7)
C2—H2B	0.9700	C11—C16	1.411 (6)
C3—C4	1.507 (6)	C12—C13	1.358 (7)
C3—H3A	0.9700	C12—H12	0.9300
C3—H3B	0.9700	C13—C14	1.392 (8)
C4—H4A	0.9700	C13—H13	0.9300
C4—H4B	0.9700	C14—C15	1.367 (6)
C5—C6	1.382 (6)	C14—H14	0.9300
C5—C10	1.403 (6)	C15—C16	1.368 (6)
C6—C7	1.386 (8)	C15—H15	0.9300
C16—N1—C5	108.9 (4)	C7—C6—H6	121.3
C16—N1—C4	125.6 (4)	C6—C7—C8	121.0 (7)
C5—N1—C4	125.5 (4)	C6—C7—H7	119.5
C2—C1—Br1	109.7 (4)	C8—C7—H7	119.5
C2—C1—H1A	109.7	C9—C8—C7	121.5 (6)
Br1—C1—H1A	109.7	C9—C8—H8	119.2
C2—C1—H1B	109.7	C7—C8—H8	119.2
Br1—C1—H1B	109.7	C8—C9—C10	118.5 (6)
H1A—C1—H1B	108.2	C8—C9—H9	120.7
C1—C2—C3	110.0 (4)	C10—C9—H9	120.7
C1—C2—H2A	109.7	C9—C10—C5	120.1 (5)
C3—C2—H2A	109.7	C9—C10—C11	133.9 (5)
C1—C2—H2B	109.7	C5—C10—C11	106.0 (4)
C3—C2—H2B	109.7	C12—C11—C16	118.5 (5)
H2A—C2—H2B	108.2	C12—C11—C10	134.4 (5)
C4—C3—C2	111.6 (4)	C16—C11—C10	107.1 (4)
C4—C3—H3A	109.3	C13—C12—C11	119.4 (5)
C2—C3—H3A	109.3	C13—C12—H12	120.3
C4—C3—H3B	109.3	C11—C12—H12	120.3
C2—C3—H3B	109.3	C12—C13—C14	121.3 (5)
H3A—C3—H3B	108.0	C12—C13—H13	119.4
N1—C4—C3	113.0 (4)	C14—C13—H13	119.4
N1—C4—H4A	109.0	C15—C14—C13	120.6 (5)
C3—C4—H4A	109.0	C15—C14—H14	119.7
N1—C4—H4B	109.0	C13—C14—H14	119.7
C3—C4—H4B	109.0	C14—C15—C16	118.6 (4)
H4A—C4—H4B	107.8	C14—C15—H15	120.7
N1—C5—C6	129.1 (5)	C16—C15—H15	120.7
N1—C5—C10	109.5 (4)	C15—C16—N1	129.8 (4)
C6—C5—C10	121.4 (5)	C15—C16—C11	121.6 (4)
C5—C6—C7	117.4 (6)	N1—C16—C11	108.5 (4)
C5—C6—H6	121.3
Br1—C1—C2—C3	178.5 (3)	C9—C10—C11—C12	−1.1 (9)
C1—C2—C3—C4	80.9 (5)	C5—C10—C11—C12	179.6 (5)
C16—N1—C4—C3	−83.0 (5)	C9—C10—C11—C16	179.2 (5)
C5—N1—C4—C3	96.9 (5)	C5—C10—C11—C16	−0.1 (5)
C2—C3—C4—N1	176.7 (4)	C16—C11—C12—C13	−0.3 (7)
C16—N1—C5—C6	179.6 (4)	C10—C11—C12—C13	180.0 (5)
C4—N1—C5—C6	−0.3 (7)	C11—C12—C13—C14	−0.3 (8)
C16—N1—C5—C10	−0.2 (5)	C12—C13—C14—C15	0.2 (8)
C4—N1—C5—C10	179.8 (4)	C13—C14—C15—C16	0.6 (7)
N1—C5—C6—C7	−180.0 (5)	C14—C15—C16—N1	179.9 (4)
C10—C5—C6—C7	−0.2 (7)	C14—C15—C16—C11	−1.2 (6)
C5—C6—C7—C8	−0.6 (8)	C5—N1—C16—C15	179.2 (4)
C6—C7—C8—C9	0.6 (10)	C4—N1—C16—C15	−0.9 (7)
C7—C8—C9—C10	0.1 (9)	C5—N1—C16—C11	0.2 (4)
C8—C9—C10—C5	−0.9 (7)	C4—N1—C16—C11	−179.9 (3)
C8—C9—C10—C11	179.9 (5)	C12—C11—C16—C15	1.1 (6)
N1—C5—C10—C9	−179.2 (4)	C10—C11—C16—C15	−179.1 (4)
C6—C5—C10—C9	0.9 (7)	C12—C11—C16—N1	−179.8 (3)
N1—C5—C10—C11	0.2 (5)	C10—C11—C16—N1	0.0 (5)
C6—C5—C10—C11	−179.6 (4)