9-(2-Bromo-eth-yl)-9H-carbazole.

In the title compound, C(14)H(12)BrN, the fused-ring system is slightly buckled as its two benzene rings are inclined to one another by 3.41 (14)°.

Related literature

For the synthesis, see: Huang et al. (2004 ▶). For a similar structure, see: Aravindan et al. (2003 ▶).

Experimental

Crystal data

C14H12BrN

M = 274.16

Monoclinic,

a = 5.417 (3) Å

b = 12.254 (6) Å

c = 17.505 (11) Å

β = 96.46 (3)°

V = 1154.6 (11) Å3

Z = 4

Mo Kα radiation

μ = 3.53 mm−1

T = 288 K

0.16 × 0.15 × 0.13 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.599, T max = 0.657

10873 measured reflections

2630 independent reflections

2093 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.082

S = 1.02

2630 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.59 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ▶); 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: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812024397/ng5265sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024397/ng5265Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812024397/ng5265Isup3.cml

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

C14H12BrN	F(000) = 552
Mr = 274.16	Dx = 1.577 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8078 reflections
a = 5.417 (3) Å	θ = 3.3–27.5°
b = 12.254 (6) Å	µ = 3.53 mm−1
c = 17.505 (11) Å	T = 288 K
β = 96.46 (3)°	Block, colorless
V = 1154.6 (11) Å3	0.16 × 0.15 × 0.13 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	2630 independent reflections
Radiation source: fine-focus sealed tube	2093 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
ω scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −6→7
Tmin = 0.599, Tmax = 0.657	k = −15→15
10873 measured reflections	l = −22→22

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0394P)2 + 0.3164P] where P = (Fo2 + 2Fc2)/3
2630 reflections	(Δ/σ)max = 0.007
145 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.59 e Å−3

Experimental. (See detailed section in the paper)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.25417 (5)	1.06970 (2)	0.430911 (16)	0.05611 (12)
C1	0.0265 (4)	0.88648 (17)	0.22679 (12)	0.0350 (4)
C2	−0.1470 (4)	0.94431 (18)	0.17824 (14)	0.0420 (5)
H2	−0.2717	0.9847	0.1974	0.050*
C3	−0.1273 (5)	0.9395 (2)	0.10030 (14)	0.0506 (6)
H3	−0.2424	0.9766	0.0664	0.061*
C4	0.0610 (5)	0.8802 (2)	0.07141 (14)	0.0504 (6)
H4	0.0706	0.8793	0.0187	0.060*
C5	0.2328 (4)	0.82325 (19)	0.11943 (13)	0.0446 (5)
H5	0.3591	0.7846	0.0997	0.054*
C6	0.2147 (4)	0.82425 (16)	0.19839 (12)	0.0356 (4)
C7	0.3499 (4)	0.77144 (17)	0.26390 (13)	0.0365 (5)
C8	0.5493 (4)	0.69878 (19)	0.27313 (15)	0.0473 (6)
H8	0.6248	0.6755	0.2309	0.057*
C9	0.6322 (5)	0.6623 (2)	0.34564 (18)	0.0572 (7)
H9	0.7654	0.6140	0.3522	0.069*
C10	0.5209 (5)	0.6961 (2)	0.40933 (16)	0.0546 (6)
H10	0.5813	0.6698	0.4577	0.066*
C11	0.3225 (4)	0.76790 (19)	0.40274 (14)	0.0465 (5)
H11	0.2484	0.7903	0.4455	0.056*
C12	0.2387 (4)	0.80512 (17)	0.32906 (13)	0.0357 (4)
C13	−0.1196 (4)	0.92796 (18)	0.35461 (14)	0.0417 (5)
H13A	−0.1073	0.8900	0.4035	0.050*
H13B	−0.2893	0.9207	0.3308	0.050*
C14	−0.0643 (4)	1.04724 (19)	0.36924 (15)	0.0466 (5)
H14A	−0.1951	1.0790	0.3956	0.056*
H14B	−0.0631	1.0846	0.3204	0.056*
N1	0.0445 (3)	0.87583 (15)	0.30599 (10)	0.0369 (4)

	U11	U22	U33	U12	U13	U23
Br1	0.05008 (16)	0.06487 (19)	0.05276 (18)	−0.01404 (11)	0.00307 (12)	−0.00812 (12)
C1	0.0349 (10)	0.0342 (10)	0.0358 (11)	−0.0048 (8)	0.0038 (8)	−0.0010 (9)
C2	0.0387 (11)	0.0423 (12)	0.0441 (13)	0.0013 (9)	0.0002 (10)	0.0007 (10)
C3	0.0585 (14)	0.0479 (13)	0.0417 (14)	−0.0059 (11)	−0.0106 (11)	0.0088 (10)
C4	0.0685 (16)	0.0497 (13)	0.0322 (12)	−0.0103 (12)	0.0017 (11)	0.0014 (10)
C5	0.0533 (13)	0.0427 (12)	0.0394 (13)	−0.0039 (10)	0.0117 (10)	−0.0061 (10)
C6	0.0370 (10)	0.0337 (10)	0.0363 (11)	−0.0056 (8)	0.0055 (9)	−0.0034 (9)
C7	0.0352 (10)	0.0339 (10)	0.0401 (12)	−0.0040 (9)	0.0035 (9)	−0.0024 (9)
C8	0.0413 (11)	0.0414 (12)	0.0589 (16)	0.0033 (10)	0.0042 (11)	−0.0067 (11)
C9	0.0480 (13)	0.0421 (13)	0.078 (2)	0.0077 (11)	−0.0076 (13)	0.0035 (13)
C10	0.0585 (14)	0.0464 (13)	0.0546 (16)	−0.0029 (12)	−0.0121 (12)	0.0163 (12)
C11	0.0520 (12)	0.0456 (12)	0.0411 (13)	−0.0052 (11)	0.0011 (11)	0.0075 (10)
C12	0.0343 (10)	0.0342 (10)	0.0379 (11)	−0.0038 (8)	0.0018 (8)	0.0014 (9)
C13	0.0355 (10)	0.0477 (13)	0.0432 (13)	−0.0033 (9)	0.0105 (9)	−0.0080 (10)
C14	0.0392 (11)	0.0496 (13)	0.0507 (15)	0.0037 (10)	0.0044 (10)	−0.0084 (11)
N1	0.0376 (9)	0.0403 (9)	0.0329 (9)	0.0028 (8)	0.0048 (7)	−0.0001 (8)

Br1—C14	1.949 (3)	C8—C9	1.373 (4)
C1—N1	1.385 (3)	C8—H8	0.9300
C1—C2	1.389 (3)	C9—C10	1.389 (4)
C1—C6	1.408 (3)	C9—H9	0.9300
C2—C3	1.382 (4)	C10—C11	1.383 (4)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.392 (4)	C11—C12	1.395 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.372 (4)	C12—N1	1.387 (3)
C4—H4	0.9300	C13—N1	1.447 (3)
C5—C6	1.397 (3)	C13—C14	1.508 (3)
C5—H5	0.9300	C13—H13A	0.9700
C6—C7	1.443 (3)	C13—H13B	0.9700
C7—C8	1.395 (3)	C14—H14A	0.9700
C7—C12	1.410 (3)	C14—H14B	0.9700
N1—C1—C2	128.8 (2)	C10—C9—H9	119.4
N1—C1—C6	109.29 (18)	C11—C10—C9	121.7 (2)
C2—C1—C6	121.8 (2)	C11—C10—H10	119.1
C3—C2—C1	117.4 (2)	C9—C10—H10	119.1
C3—C2—H2	121.3	C10—C11—C12	117.0 (2)
C1—C2—H2	121.3	C10—C11—H11	121.5
C2—C3—C4	121.5 (2)	C12—C11—H11	121.5
C2—C3—H3	119.3	N1—C12—C11	129.1 (2)
C4—C3—H3	119.3	N1—C12—C7	109.03 (19)
C5—C4—C3	121.1 (2)	C11—C12—C7	121.9 (2)
C5—C4—H4	119.5	N1—C13—C14	113.85 (19)
C3—C4—H4	119.5	N1—C13—H13A	108.8
C4—C5—C6	118.9 (2)	C14—C13—H13A	108.8
C4—C5—H5	120.5	N1—C13—H13B	108.8
C6—C5—H5	120.5	C14—C13—H13B	108.8
C5—C6—C1	119.2 (2)	H13A—C13—H13B	107.7
C5—C6—C7	134.2 (2)	C13—C14—Br1	112.18 (16)
C1—C6—C7	106.57 (18)	C13—C14—H14A	109.2
C8—C7—C12	119.3 (2)	Br1—C14—H14A	109.2
C8—C7—C6	134.1 (2)	C13—C14—H14B	109.2
C12—C7—C6	106.66 (18)	Br1—C14—H14B	109.2
C9—C8—C7	118.9 (2)	H14A—C14—H14B	107.9
C9—C8—H8	120.5	C12—N1—C1	108.42 (17)
C7—C8—H8	120.5	C12—N1—C13	126.90 (19)
C8—C9—C10	121.2 (2)	C1—N1—C13	124.65 (18)
C8—C9—H9	119.4