4-Bromo-N-phenyl-aniline.

In the title compound, C(12)H(10)BrN, the dihedral angle between the benzene rings is 52.5 (1)°, whereas the pitch angles, or the angles between the mean plane of each aryl group 'propeller blade' and the plane defined by the aryl bridging C-N-C angle, are 19.6 (2) and 36.2 (3)°. While the N-H group is not involved in hydrogen-bonding inter-actions, the structure exhibits a network of inter-molecular C-H⋯π and N-H⋯π inter-actions.

Related literature

The title compound is an amine analogue of n class="Chemical">brominated diphenyl ether flame retardant materials commonly used in household items. For information on environmental and health concerns related to brominated flame retardants, see: de Wit (2002 ▶); Lunder et al. (2010 ▶). For the synthesis, see: He et al. (2008 ▶); Sus (1947 ▶). For a related structure and information on C—H⋯π and N—H⋯π inter­actions, see: Krzymiński et al. (2009 ▶). For a description of the pitch angle in similar diphenyl structures, see: Duong & Tanski (2011 ▶); Lim & Tanski (2007 ▶).

Experimental

Crystal data

C12H10BrN

M = 248.12

Orthorhombic,

a = 15.6741 (6) Å

b = 17.7531 (7) Å

c = 7.3608 (3) Å

V = 2048.24 (14) Å3

Z = 8

Mo Kα radiation

μ = 3.97 mm−1

T = 125 K

0.31 × 0.21 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2007 ▶) T min = 0.373, T max = 0.857

31081 measured reflections

3137 independent reflections

2552 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.118

S = 1.07

3137 reflections

130 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.72 e Å−3

Δρmin = −0.77 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAIn class="Chemical">NT (Bruker, 2007 ▶); data reduction: SAINT; 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 and Mercury (Macrae et al., 2006 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681101052X/om2415sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101052X/om2415Isup2.hkl

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

C12H10BrN	F(000) = 992
Mr = 248.12	Dx = 1.609 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 9926 reflections
a = 15.6741 (6) Å	θ = 2.3–30.2°
b = 17.7531 (7) Å	µ = 3.97 mm−1
c = 7.3608 (3) Å	T = 125 K
V = 2048.24 (14) Å3	Plate, colourless
Z = 8	0.31 × 0.21 × 0.04 mm

Bruker APEXII CCD diffractometer	3137 independent reflections
Radiation source: fine-focus sealed tube	2552 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 30.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker 2007)	h = −22→22
Tmin = 0.373, Tmax = 0.857	k = −25→25
31081 measured reflections	l = −10→10

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0513P)2 + 4.1415P] where P = (Fo2 + 2Fc2)/3
3137 reflections	(Δ/σ)max = 0.001
130 parameters	Δρmax = 1.72 e Å−3
1 restraint	Δρmin = −0.77 e Å−3

Experimental. A suitable crystal was mounted in a nylon loop with Paratone-N cryoprotectant oil.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes and the e.s.d. for hydrogen-pi acceptor interactions) 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. Esds for the hydrogen-pi acceptor interactions are taken as the e.s.d.'s on the hydrogen donor to mean plane of the pi-acceptor distances.

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	0.14415 (2)	0.595132 (18)	0.26943 (4)	0.03453 (12)
N1	−0.02798 (16)	0.68765 (12)	0.9753 (3)	0.0256 (5)
H1	−0.009 (2)	0.7273 (14)	1.025 (4)	0.031*
C1	0.09072 (18)	0.62304 (14)	0.4908 (4)	0.0237 (5)
C2	0.13506 (17)	0.66570 (15)	0.6173 (4)	0.0250 (5)
H2	0.1920	0.6811	0.5936	0.030*
C3	0.09542 (18)	0.68562 (15)	0.7787 (4)	0.0248 (5)
H3	0.1258	0.7148	0.8654	0.030*
C4	0.01153 (17)	0.66358 (14)	0.8166 (3)	0.0220 (5)
C5	−0.03227 (17)	0.62058 (14)	0.6857 (3)	0.0225 (5)
H5	−0.0893	0.6052	0.7082	0.027*
C6	0.00745 (18)	0.60043 (14)	0.5232 (3)	0.0228 (5)
H6	−0.0224	0.5714	0.4353	0.027*
C7	−0.08697 (16)	0.64678 (14)	1.0792 (3)	0.0220 (5)
C8	−0.09352 (17)	0.56827 (14)	1.0688 (4)	0.0233 (5)
H8	−0.0593	0.5412	0.9846	0.028*
C9	−0.14950 (19)	0.52990 (17)	1.1805 (4)	0.0294 (6)
H9	−0.1534	0.4766	1.1721	0.035*
C10	−0.2008 (2)	0.5685 (2)	1.3063 (4)	0.0343 (6)
H10	−0.2389	0.5419	1.3835	0.041*
C11	−0.19422 (19)	0.6463 (2)	1.3148 (4)	0.0338 (6)
H11	−0.2284	0.6733	1.3993	0.041*
C12	−0.13888 (18)	0.68566 (16)	1.2028 (4)	0.0271 (5)
H12	−0.1361	0.7390	1.2098	0.033*

	U11	U22	U33	U12	U13	U23
Br1	0.03463 (18)	0.03743 (18)	0.03153 (17)	0.00533 (12)	0.00963 (12)	−0.00285 (11)
N1	0.0360 (12)	0.0194 (9)	0.0213 (10)	−0.0046 (9)	0.0032 (9)	−0.0044 (8)
C1	0.0275 (12)	0.0196 (11)	0.0241 (12)	0.0050 (9)	0.0014 (10)	0.0036 (9)
C2	0.0217 (12)	0.0233 (11)	0.0301 (13)	−0.0011 (9)	−0.0001 (10)	0.0059 (10)
C3	0.0286 (12)	0.0211 (11)	0.0246 (12)	−0.0041 (9)	−0.0039 (10)	0.0020 (9)
C4	0.0299 (13)	0.0175 (10)	0.0187 (11)	−0.0007 (9)	−0.0005 (9)	0.0014 (8)
C5	0.0238 (12)	0.0238 (11)	0.0200 (11)	−0.0010 (9)	−0.0011 (9)	−0.0012 (9)
C6	0.0283 (12)	0.0203 (11)	0.0198 (11)	0.0000 (9)	−0.0017 (9)	−0.0003 (9)
C7	0.0233 (12)	0.0232 (11)	0.0194 (11)	0.0023 (9)	−0.0033 (9)	−0.0004 (9)
C8	0.0255 (12)	0.0219 (11)	0.0225 (11)	0.0024 (9)	−0.0021 (9)	−0.0016 (9)
C9	0.0315 (14)	0.0302 (13)	0.0266 (13)	−0.0056 (11)	−0.0024 (11)	0.0023 (10)
C10	0.0287 (14)	0.0461 (17)	0.0280 (14)	−0.0090 (13)	0.0008 (11)	−0.0012 (12)
C11	0.0255 (13)	0.0497 (18)	0.0263 (13)	0.0019 (12)	0.0033 (11)	−0.0095 (12)
C12	0.0275 (13)	0.0283 (13)	0.0257 (12)	0.0046 (10)	−0.0027 (10)	−0.0053 (10)

Br1—C1	1.898 (3)	C6—H6	0.9500
N1—C4	1.389 (3)	C7—C8	1.400 (4)
N1—C7	1.402 (3)	C7—C12	1.402 (4)
N1—H1	0.849 (18)	C8—C9	1.382 (4)
C1—C6	1.386 (4)	C8—H8	0.9500
C1—C2	1.387 (4)	C9—C10	1.404 (4)
C2—C3	1.387 (4)	C9—H9	0.9500
C2—H2	0.9500	C10—C11	1.388 (5)
C3—C4	1.400 (4)	C10—H10	0.9500
C3—H3	0.9500	C11—C12	1.385 (4)
C4—C5	1.408 (4)	C11—H11	0.9500
C5—C6	1.395 (4)	C12—H12	0.9500
C5—H5	0.9500
C4—N1—C7	126.4 (2)	C5—C6—H6	120.2
C4—N1—H1	117 (2)	C8—C7—N1	122.3 (2)
C7—N1—H1	115 (2)	C8—C7—C12	118.9 (2)
C6—C1—C2	121.0 (2)	N1—C7—C12	118.8 (2)
C6—C1—Br1	119.2 (2)	C9—C8—C7	120.3 (3)
C2—C1—Br1	119.9 (2)	C9—C8—H8	119.8
C3—C2—C1	119.3 (2)	C7—C8—H8	119.8
C3—C2—H2	120.3	C8—C9—C10	121.0 (3)
C1—C2—H2	120.3	C8—C9—H9	119.5
C2—C3—C4	121.4 (2)	C10—C9—H9	119.5
C2—C3—H3	119.3	C11—C10—C9	118.2 (3)
C4—C3—H3	119.3	C11—C10—H10	120.9
N1—C4—C3	120.0 (2)	C9—C10—H10	120.9
N1—C4—C5	121.6 (2)	C12—C11—C10	121.4 (3)
C3—C4—C5	118.2 (2)	C12—C11—H11	119.3
C6—C5—C4	120.5 (2)	C10—C11—H11	119.3
C6—C5—H5	119.7	C11—C12—C7	120.1 (3)
C4—C5—H5	119.7	C11—C12—H12	120.0
C1—C6—C5	119.6 (2)	C7—C12—H12	120.0
C1—C6—H6	120.2
C6—C1—C2—C3	0.3 (4)	C4—C5—C6—C1	0.0 (4)
Br1—C1—C2—C3	−179.87 (19)	C4—N1—C7—C8	20.8 (4)
C1—C2—C3—C4	0.0 (4)	C4—N1—C7—C12	−161.7 (3)
C7—N1—C4—C3	−145.7 (3)	N1—C7—C8—C9	176.6 (3)
C7—N1—C4—C5	38.0 (4)	C12—C7—C8—C9	−0.8 (4)
C2—C3—C4—N1	−176.7 (2)	C7—C8—C9—C10	0.0 (4)
C2—C3—C4—C5	−0.2 (4)	C8—C9—C10—C11	0.4 (4)
N1—C4—C5—C6	176.6 (2)	C9—C10—C11—C12	0.1 (4)
C3—C4—C5—C6	0.3 (4)	C10—C11—C12—C7	−1.0 (4)
C2—C1—C6—C5	−0.3 (4)	C8—C7—C12—C11	1.3 (4)
Br1—C1—C6—C5	179.89 (19)	N1—C7—C12—C11	−176.2 (3)

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg2i	0.95	2.69	3.404 (3)	132
N1—H1···Cg1ii	0.85 (2)	2.65	3.501 (2)	175
C9—H9···Cg1iii	0.95	2.96	3.651 (3)	131

Table 1

C—H⋯π and N—H⋯π interactions (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cg2i	0.95	2.69	3.404 (3)	132
N1—H1⋯Cg1ii	0.85 (2)	2.65	3.501 (2)	175
C9—H9⋯Cg1iii	0.95	2.96	3.651 (3)	131

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