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

In the title mol-ecule, C18H12BrN, the 4-bromo-phenyl ring is inclined to the mean plane of the carbazole moiety (r.m.s. devation = 0.027 Å) by 49.87 (5)°. In the crystal, molecules stack along [001] and are linked by C-H⋯π interactions forming a corrugated two-dimensional network lying parallel to (100).

Related literature

For isostructural crystal structures, see: Saha & Samanta (1999 ▶); Chen et al. (2005 ▶). For related carbazole-based crystal structures, see: Kim et al. (2011 ▶); Liu et al. (2010 ▶); Wu et al. (2007 ▶); Chen et al. (2012 ▶). For a chemically related non-isostructural compound, see: Xie et al. (2012 ▶). For applications of aryl­amines as functional materials, see: Shirota & Kageyama (2007 ▶); Tao et al. (2011 ▶); Yook & Lee (2012 ▶); Kautny et al. (2014 ▶). For isostructurality, see: Kálmán et al. (1999 ▶). For merotypism and its application to organic compounds, see: Ferraris et al. (2004 ▶); Stöger et al. (2012 ▶). For the synthesis of the title compound, see: Xu et al. (2007 ▶).

Experimental

Crystal data

C18H12BrN

M = 322.2

Monoclinic,

a = 8.4137 (3) Å

b = 20.1179 (7) Å

c = 8.6346 (3) Å

β = 108.5322 (14)°

V = 1385.76 (8) Å3

Z = 4

Mo Kα radiation

μ = 2.95 mm−1

T = 100 K

0.75 × 0.55 × 0.42 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.16, T max = 0.29

53140 measured reflections

5056 independent reflections

4340 reflections with I > 3σ(I)

R int = 0.035

Refinement

R[F 2 > 3σ(F 2)] = 0.031

wR(F) = 0.047

S = 1.69

5056 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.51 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT-Plus (Bruker, 2013 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ▶); molecular graphics: ATOMS (Dowty, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814003705/kj2237sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003705/kj2237Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814003705/kj2237Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H12BrN	F(000) = 648
Mr = 322.2	Dx = 1.544 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ycb	Cell parameters from 25237 reflections
a = 8.4137 (3) Å	θ = 2.5–32.5°
b = 20.1179 (7) Å	µ = 2.95 mm−1
c = 8.6346 (3) Å	T = 100 K
β = 108.5322 (14)°	Block, clear colourless
V = 1385.76 (8) Å3	0.75 × 0.55 × 0.42 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	5056 independent reflections
Radiation source: X-ray tube	4340 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.035
ω and φ scans	θmax = 32.8°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −12→12
Tmin = 0.16, Tmax = 0.29	k = −30→30
53140 measured reflections	l = −13→13

Refinement on F	Primary atom site location: iterative
R[F2 > 2σ(F2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.047	H-atom parameters constrained
S = 1.69	Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0004F2)
5056 reflections	(Δ/σ)max = 0.026
181 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.51 e Å−3
48 constraints

	x	y	z	Uiso*/Ueq
Br1	0.84651 (2)	−0.036314 (8)	−0.405902 (18)	0.02427 (6)
N1	0.51185 (14)	0.12342 (5)	0.00001 (13)	0.0116 (3)
C1	0.58687 (16)	0.08548 (6)	−0.09658 (15)	0.0111 (3)
C2	0.69269 (18)	0.03277 (6)	−0.02622 (17)	0.0133 (4)
C3	0.77018 (17)	−0.00373 (6)	−0.11813 (17)	0.0139 (4)
C4	0.73532 (17)	0.01171 (7)	−0.28261 (16)	0.0139 (4)
C5	0.62817 (17)	0.06309 (7)	−0.35594 (16)	0.0148 (4)
C6	0.55565 (17)	0.10094 (7)	−0.26077 (15)	0.0135 (3)
C7	0.34167 (16)	0.13791 (6)	−0.03947 (16)	0.0118 (3)
C8	0.21016 (17)	0.12051 (7)	−0.17824 (16)	0.0147 (4)
C9	0.04953 (18)	0.13772 (7)	−0.18154 (18)	0.0174 (4)
C10	0.01993 (18)	0.17175 (7)	−0.05191 (19)	0.0190 (4)
C11	0.15091 (18)	0.18942 (7)	0.08536 (18)	0.0172 (4)
C12	0.31464 (17)	0.17212 (6)	0.09265 (16)	0.0127 (4)
C13	0.47576 (17)	0.17913 (6)	0.21673 (16)	0.0122 (3)
C14	0.52962 (19)	0.20908 (6)	0.37103 (17)	0.0164 (4)
C15	0.6979 (2)	0.20772 (7)	0.46009 (17)	0.0186 (4)
C16	0.81376 (18)	0.17722 (7)	0.39656 (17)	0.0168 (4)
C17	0.76424 (17)	0.14676 (6)	0.24474 (16)	0.0143 (4)
C18	0.59415 (16)	0.14789 (6)	0.15611 (15)	0.0116 (3)
H1c2	0.712034	0.021682	0.086423	0.016*
H1c3	0.846464	−0.038992	−0.069149	0.0167*
H1c5	0.604265	0.072462	−0.470097	0.0178*
H1c6	0.484129	0.13771	−0.308549	0.0162*
H1c8	0.229898	0.097553	−0.267885	0.0176*
H1c9	−0.043798	0.125999	−0.275106	0.0208*
H1c10	−0.092883	0.182992	−0.058358	0.0228*
H1c11	0.130161	0.212998	0.17367	0.0206*
H1c14	0.450589	0.230279	0.414296	0.0197*
H1c15	0.735971	0.227799	0.566404	0.0223*
H1c16	0.930439	0.177463	0.459918	0.0202*
H1c17	0.844122	0.125706	0.202336	0.0172*

	U11	U22	U33	U12	U13	U23
Br1	0.02113 (9)	0.03450 (10)	0.02083 (9)	0.00656 (6)	0.01183 (6)	−0.00729 (6)
N1	0.0095 (5)	0.0143 (5)	0.0113 (4)	0.0012 (4)	0.0040 (4)	−0.0020 (4)
C1	0.0106 (5)	0.0134 (5)	0.0109 (5)	−0.0005 (4)	0.0055 (4)	−0.0013 (4)
C2	0.0139 (6)	0.0133 (5)	0.0145 (6)	−0.0009 (4)	0.0069 (5)	0.0000 (4)
C3	0.0127 (6)	0.0132 (5)	0.0174 (6)	0.0004 (4)	0.0071 (5)	−0.0009 (4)
C4	0.0121 (5)	0.0173 (6)	0.0148 (5)	−0.0017 (5)	0.0079 (5)	−0.0046 (5)
C5	0.0147 (6)	0.0199 (6)	0.0116 (5)	−0.0005 (5)	0.0066 (5)	−0.0015 (5)
C6	0.0125 (5)	0.0166 (6)	0.0120 (5)	0.0007 (4)	0.0047 (4)	0.0003 (4)
C7	0.0105 (5)	0.0114 (5)	0.0147 (5)	0.0016 (4)	0.0059 (4)	0.0011 (4)
C8	0.0128 (6)	0.0167 (6)	0.0145 (5)	0.0000 (4)	0.0042 (4)	0.0010 (4)
C9	0.0126 (6)	0.0192 (6)	0.0192 (6)	0.0008 (5)	0.0034 (5)	0.0048 (5)
C10	0.0130 (6)	0.0174 (6)	0.0286 (7)	0.0043 (5)	0.0094 (5)	0.0044 (5)
C11	0.0167 (6)	0.0140 (6)	0.0249 (7)	0.0037 (5)	0.0123 (5)	0.0008 (5)
C12	0.0134 (5)	0.0105 (5)	0.0161 (6)	0.0016 (4)	0.0073 (5)	0.0008 (4)
C13	0.0157 (6)	0.0091 (5)	0.0135 (5)	0.0001 (4)	0.0071 (4)	−0.0005 (4)
C14	0.0222 (7)	0.0117 (5)	0.0172 (6)	0.0004 (5)	0.0090 (5)	−0.0034 (4)
C15	0.0260 (7)	0.0148 (6)	0.0140 (6)	−0.0028 (5)	0.0051 (5)	−0.0039 (5)
C16	0.0181 (6)	0.0151 (6)	0.0158 (6)	−0.0031 (5)	0.0033 (5)	−0.0003 (5)
C17	0.0139 (6)	0.0147 (5)	0.0144 (5)	0.0000 (4)	0.0046 (5)	−0.0003 (4)
C18	0.0133 (5)	0.0109 (5)	0.0113 (5)	−0.0007 (4)	0.0051 (4)	−0.0011 (4)

Br1—C4	1.8909 (15)	C9—C10	1.400 (2)
N1—C1	1.4182 (19)	C9—H1c9	0.96
N1—C7	1.3932 (17)	C10—C11	1.3840 (18)
N1—C18	1.3947 (15)	C10—H1c10	0.96
C1—C2	1.3937 (17)	C11—C12	1.403 (2)
C1—C6	1.3925 (18)	C11—H1c11	0.96
C2—C3	1.387 (2)	C12—C13	1.4430 (17)
C2—H1c2	0.96	C13—C14	1.3999 (18)
C3—C4	1.3910 (19)	C13—C18	1.412 (2)
C3—H1c3	0.96	C14—C15	1.380 (2)
C4—C5	1.3853 (18)	C14—H1c14	0.96
C5—C6	1.395 (2)	C15—C16	1.403 (2)
C5—H1c5	0.96	C15—H1c15	0.96
C6—H1c6	0.96	C16—C17	1.3858 (19)
C7—C8	1.3928 (16)	C16—H1c16	0.96
C7—C12	1.411 (2)	C17—C18	1.3922 (18)
C8—C9	1.387 (2)	C17—H1c17	0.96
C8—H1c8	0.96
C1—N1—C7	125.70 (10)	C10—C9—H1c9	119.15
C1—N1—C18	125.54 (11)	C9—C10—C11	120.97 (14)
C7—N1—C18	108.58 (12)	C9—C10—H1c10	119.51
N1—C1—C2	119.68 (12)	C11—C10—H1c10	119.51
N1—C1—C6	120.22 (11)	C10—C11—C12	118.56 (14)
C2—C1—C6	120.10 (13)	C10—C11—H1c11	120.72
C1—C2—C3	120.32 (13)	C12—C11—H1c11	120.72
C1—C2—H1c2	119.84	C7—C12—C11	119.54 (11)
C3—C2—H1c2	119.84	C7—C12—C13	107.05 (12)
C2—C3—C4	118.76 (12)	C11—C12—C13	133.35 (13)
C2—C3—H1c3	120.62	C12—C13—C14	133.82 (14)
C4—C3—H1c3	120.62	C12—C13—C18	106.75 (11)
Br1—C4—C3	118.63 (10)	C14—C13—C18	119.43 (12)
Br1—C4—C5	119.37 (11)	C13—C14—C15	119.10 (15)
C3—C4—C5	121.92 (14)	C13—C14—H1c14	120.45
C4—C5—C6	118.75 (12)	C15—C14—H1c14	120.45
C4—C5—H1c5	120.62	C14—C15—C16	120.54 (13)
C6—C5—H1c5	120.63	C14—C15—H1c15	119.73
C1—C6—C5	120.10 (12)	C16—C15—H1c15	119.73
C1—C6—H1c6	119.95	C15—C16—C17	121.73 (12)
C5—C6—H1c6	119.95	C15—C16—H1c16	119.13
N1—C7—C8	129.17 (13)	C17—C16—H1c16	119.13
N1—C7—C12	108.74 (10)	C16—C17—C18	117.40 (14)
C8—C7—C12	122.00 (13)	C16—C17—H1c17	121.3
C7—C8—C9	117.23 (13)	C18—C17—H1c17	121.3
C7—C8—H1c8	121.39	N1—C18—C13	108.87 (11)
C9—C8—H1c8	121.39	N1—C18—C17	129.30 (14)
C8—C9—C10	121.70 (12)	C13—C18—C17	121.78 (12)
C8—C9—H1c9	119.15

D—H···A	D—H	H···A	D···A	D—H···A
C3—H1C3···Cg3i	0.96	2.57	3.3237 (14)	135
C5—H1C5···Cg4ii	0.96	2.96	3.7527 (15)	141
C14—H1C14···Cg1iii	0.96	2.79	3.5367 (14)	135

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg3 and Cg4 are the centroids of the N1/C7/C12/C13/C18, C7–C12 and C13–C18 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H1C3⋯Cg3i	0.96	2.57	3.3237 (14)	135
C5—H1C5⋯Cg4ii	0.96	2.96	3.7527 (15)	141
C14—H1C14⋯Cg1iii	0.96	2.79	3.5367 (14)	135

Symmetry codes: (i) ; (ii) ; (iii) .