N,N-Bis(2-bromo-ethyl)aniline.

The mol-ecule of the title compound, C(10)H(13)Br(2)N, has a twofold rotation axis along the N-C(phen-yl) bond. The compound shows a slightly distorted trigonal planar geometry around the N atom. The structural study shows the presence of inter-molecular C-H⋯Br inter-actions, resulting in a three-dimensional supra-molecular architecture.

Related literature

For related literature, see: Bricks et al. (2005 ▶); Chapman & Triggle (1963 ▶); Ross (1949 ▶); Hartley et al. (2000 ▶); Palmer et al. (1990 ▶); Panthananickal et al. (1978 ▶).

Experimental

Crystal data

C10H13Br2N

M = 307.03

Orthorhombic,

a = 13.682 (12) Å

b = 13.926 (12) Å

c = 12.215 (10) Å

V = 2327 (3) Å3

Z = 8

Mo Kα radiation

μ = 6.92 mm−1

T = 297 (2) K

0.27 × 0.23 × 0.09 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.155, T max = 0.534

4145 measured reflections

1191 independent reflections

893 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.088

S = 0.99

1191 reflections

61 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.41 e Å−3

Absolute structure: Flack (1983 ▶), 564 Friedel pairs

Flack parameter: 0.05 (3)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2000 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2001 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg & Putz, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2007 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807056279/cf2168sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807056279/cf2168Isup2.hkl

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

C10H13Br2N	F000 = 1200
Mr = 307.03	Dx = 1.752 Mg m−3
Orthorhombic, Fdd2	Mo Kα radiation λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 1908 reflections
a = 13.682 (12) Å	θ = 2.7–24.3º
b = 13.926 (12) Å	µ = 6.92 mm−1
c = 12.215 (10) Å	T = 297 (2) K
V = 2327 (3) Å3	Block, colourless
Z = 8	0.27 × 0.23 × 0.09 mm

Bruker SMART APEX diffractometer	1191 independent reflections
Radiation source: fine-focus sealed tube	893 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.047
T = 297(2) K	θmax = 26.4º
φ and ω scans	θmin = 2.7º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −17→17
Tmin = 0.155, Tmax = 0.534	k = −17→17
4145 measured reflections	l = −15→15

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.037	w = 1/[σ2(Fo2) + (0.0396P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.088	(Δ/σ)max < 0.001
S = 0.99	Δρmax = 0.61 e Å−3
1191 reflections	Δρmin = −0.41 e Å−3
61 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 564 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.05 (3)
Secondary atom site location: difference Fourier map

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
C6	0.4227 (4)	0.2321 (4)	0.3885 (5)	0.0665 (14)
H6A	0.4458	0.2250	0.4632	0.080*
H6B	0.4729	0.2653	0.3472	0.080*
C5	0.3302 (4)	0.2919 (4)	0.3884 (4)	0.0595 (14)
H5A	0.3448	0.3544	0.4193	0.071*
H5B	0.3097	0.3016	0.3132	0.071*
Br1	0.40184 (5)	0.10577 (5)	0.32538 (10)	0.0854 (3)
C1	0.2500	0.2500	0.5638 (6)	0.0453 (14)
N1	0.2500	0.2500	0.4487 (4)	0.0521 (13)
C2	0.3190 (3)	0.3010 (4)	0.6240 (4)	0.0569 (13)
H2	0.3669	0.3356	0.5871	0.068*
C3	0.3183 (5)	0.3014 (4)	0.7376 (5)	0.0687 (16)
H3	0.3649	0.3371	0.7753	0.082*
C4	0.2500	0.2500	0.7949 (7)	0.074 (2)
H4	0.2500	0.2500	0.8710	0.089*

	U11	U22	U33	U12	U13	U23
C6	0.053 (3)	0.067 (3)	0.079 (4)	−0.001 (2)	0.012 (3)	−0.004 (3)
C5	0.071 (3)	0.052 (3)	0.056 (3)	0.007 (3)	0.008 (3)	0.008 (2)
Br1	0.0888 (4)	0.0783 (4)	0.0891 (4)	0.0256 (3)	0.0001 (4)	−0.0161 (4)
C1	0.047 (3)	0.036 (3)	0.053 (4)	0.012 (3)	0.000	0.000
N1	0.044 (3)	0.062 (3)	0.051 (3)	0.000 (3)	0.000	0.000
C2	0.045 (3)	0.051 (3)	0.075 (3)	−0.004 (2)	−0.004 (2)	−0.007 (3)
C3	0.061 (3)	0.069 (4)	0.076 (4)	0.015 (3)	−0.025 (3)	−0.014 (3)
C4	0.078 (6)	0.083 (6)	0.062 (5)	0.019 (5)	0.000	0.000

C6—C5	1.515 (7)	C1—C2	1.391 (6)
C6—Br1	1.942 (6)	C1—N1	1.406 (9)
C6—H6A	0.970	C2—C3	1.388 (8)
C6—H6B	0.970	C2—H2	0.930
C5—N1	1.445 (6)	C3—C4	1.370 (8)
C5—H5A	0.970	C3—H3	0.930
C5—H5B	0.970	C4—H4	0.930
C5—C6—Br1	112.0 (4)	C2—C1—N1	121.9 (3)
C5—C6—H6A	109.2	C1—N1—C5	120.7 (3)
Br1—C6—H6A	109.2	C1—N1—C5i	120.7 (3)
C5—C6—H6B	109.2	C5—N1—C5i	118.6 (6)
Br1—C6—H6B	109.2	C3—C2—C1	121.7 (5)
H6A—C6—H6B	107.9	C3—C2—H2	119.1
N1—C5—C6	114.3 (4)	C1—C2—H2	119.1
N1—C5—H5A	108.7	C4—C3—C2	120.9 (6)
C6—C5—H5A	108.7	C4—C3—H3	119.6
N1—C5—H5B	108.7	C2—C3—H3	119.6
C6—C5—H5B	108.7	C3—C4—C3i	118.6 (8)
H5A—C5—H5B	107.6	C3—C4—H4	120.7
C2i—C1—C2	116.2 (7)	C3i—C4—H4	120.7
C2i—C1—N1	121.9 (3)
Br1—C6—C5—N1	59.5 (6)	C6—C5—N1—C5i	−105.7 (5)
C2i—C1—N1—C5	−171.0 (3)	C2i—C1—C2—C3	−0.5 (4)
C2—C1—N1—C5	9.0 (3)	N1—C1—C2—C3	179.5 (4)
C2i—C1—N1—C5i	8.9 (3)	C1—C2—C3—C4	1.1 (7)
C2—C1—N1—C5i	−171.1 (3)	C2—C3—C4—C3i	−0.5 (4)
C6—C5—N1—C1	74.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···Br1ii	0.97	3.05	3.933 (6)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5B⋯Br1i	0.97	3.05	3.933 (6)	153

Symmetry code: (i) .