2,5-Bis(bromo-meth-yl)biphen-yl.

In the title compound, C(14)H(12)Br(2), the Br atoms lie on opposite sides of their ring plane. The biphenyl inter-planar angle is 53.52 (8)°. The packing is characterized by several H⋯Br contacts to each Br atom, but at long distances of 3.07-3.43 Å.

Related literature

For the structures of bromo­methyl-substituted aromatic ring systems, see: Jones & Kuś (2005 ▶, 2007 ▶); Jones et al. (2007 ▶). For the synthesis, see: Czuchajowski & Zemanek (1990 ▶); For a related structure with a similar conformation, see: Obrey et al. (2002 ▶). For the phenomenon of tertiary contacts, see: Du Mont et al. (2008 ▶);

Experimental

Crystal data

C14H12Br2

M = 340.06

Monoclinic,

a = 33.084 (4) Å

b = 4.3354 (6) Å

c = 18.017 (2) Å

β = 103.702 (4)°

V = 2510.7 (5) Å3

Z = 8

Mo Kα radiation

μ = 6.43 mm−1

T = 133 K

0.25 × 0.10 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.316, T max = 0.566 (expected range = 0.294–0.526)

18269 measured reflections

3120 independent reflections

2518 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.085

S = 1.05

3120 reflections

145 parameters

H-atom parameters constrained

Δρmax = 1.00 e Å−3

Δρmin = −1.00 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1994 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018066/bt2951sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018066/bt2951Isup2.hkl

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

C14H12Br2	F(000) = 1328
Mr = 340.06	Dx = 1.799 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 33.084 (4) Å	Cell parameters from 6730 reflections
b = 4.3354 (6) Å	θ = 2.3–28.8°
c = 18.017 (2) Å	µ = 6.43 mm−1
β = 103.702 (4)°	T = 133 K
V = 2510.7 (5) Å3	Prism, colourless
Z = 8	0.25 × 0.10 × 0.10 mm

Bruker SMART 1000 CCD area-detector diffractometer	3120 independent reflections
Radiation source: fine-focus sealed tube	2518 reflections with I > 2σ(I)
graphite	Rint = 0.040
Detector resolution: 8.192 pixels mm-1	θmax = 28.3°, θmin = 1.3°
φ and ω scans	h = −44→44
Absorption correction: multi-scan (SADABS; Bruker, 1998)	k = −5→5
Tmin = 0.316, Tmax = 0.566	l = −24→24
18269 measured reflections

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0515P)2 + 1.9201P] where P = (Fo2 + 2Fc2)/3
3120 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 1.00 e Å−3
0 restraints	Δρmin = −1.00 e Å−3

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
Br1	0.219743 (8)	0.60712 (7)	0.152339 (16)	0.02600 (10)
Br2	−0.025878 (8)	0.25836 (8)	0.108852 (19)	0.03229 (11)
C1	0.11964 (8)	0.5306 (6)	0.22477 (14)	0.0176 (5)
C2	0.13425 (8)	0.6193 (6)	0.16080 (15)	0.0179 (5)
C3	0.11266 (8)	0.5205 (7)	0.08827 (15)	0.0209 (5)
H3	0.1219	0.5856	0.0447	0.025*
C4	0.07831 (9)	0.3310 (7)	0.07839 (17)	0.0244 (6)
H4	0.0647	0.2621	0.0287	0.029*
C5	0.06355 (8)	0.2407 (6)	0.14127 (17)	0.0222 (6)
C6	0.08387 (8)	0.3445 (7)	0.21324 (16)	0.0209 (6)
H6	0.0733	0.2883	0.2560	0.025*
C7	0.17006 (8)	0.8325 (7)	0.16619 (16)	0.0211 (6)
H7A	0.1765	0.9347	0.2168	0.025*
H7B	0.1625	0.9942	0.1265	0.025*
C8	0.02710 (8)	0.0280 (7)	0.13151 (19)	0.0304 (7)
H8A	0.0294	−0.0937	0.1788	0.037*
H8B	0.0273	−0.1176	0.0893	0.037*
C11	0.14006 (8)	0.6257 (7)	0.30405 (14)	0.0187 (5)
C12	0.18247 (9)	0.5758 (7)	0.33539 (16)	0.0247 (6)
H12	0.1989	0.4783	0.3056	0.030*
C13	0.20058 (9)	0.6669 (8)	0.40922 (17)	0.0300 (7)
H13	0.2293	0.6288	0.4300	0.036*
C14	0.17707 (10)	0.8145 (8)	0.45354 (17)	0.0306 (7)
H14	0.1898	0.8822	0.5038	0.037*
C15	0.13489 (9)	0.8614 (8)	0.42342 (16)	0.0279 (7)
H15	0.1186	0.9615	0.4532	0.033*
C16	0.11642 (9)	0.7626 (7)	0.34998 (16)	0.0225 (6)
H16	0.0873	0.7883	0.3306	0.027*

	U11	U22	U33	U12	U13	U23
Br1	0.01373 (14)	0.03068 (18)	0.03439 (16)	−0.00368 (11)	0.00730 (10)	−0.00446 (13)
Br2	0.01203 (15)	0.0309 (2)	0.0514 (2)	−0.00186 (11)	0.00244 (12)	0.00305 (14)
C1	0.0114 (11)	0.0171 (13)	0.0231 (12)	0.0036 (10)	0.0018 (9)	0.0018 (11)
C2	0.0130 (11)	0.0162 (13)	0.0236 (12)	0.0016 (10)	0.0027 (9)	0.0000 (11)
C3	0.0177 (12)	0.0208 (14)	0.0234 (12)	0.0028 (11)	0.0036 (10)	0.0026 (11)
C4	0.0165 (13)	0.0260 (15)	0.0273 (14)	0.0032 (11)	−0.0013 (10)	−0.0023 (12)
C5	0.0120 (12)	0.0158 (14)	0.0371 (15)	0.0029 (10)	0.0025 (11)	−0.0001 (12)
C6	0.0135 (12)	0.0208 (14)	0.0278 (13)	0.0025 (10)	0.0033 (10)	0.0051 (11)
C7	0.0174 (13)	0.0201 (14)	0.0264 (13)	0.0016 (11)	0.0064 (10)	0.0013 (11)
C8	0.0137 (13)	0.0213 (15)	0.0528 (19)	0.0011 (12)	0.0009 (12)	0.0013 (14)
C11	0.0139 (12)	0.0221 (14)	0.0194 (12)	0.0007 (10)	0.0027 (9)	0.0045 (11)
C12	0.0162 (13)	0.0326 (17)	0.0252 (13)	0.0037 (12)	0.0049 (10)	−0.0003 (12)
C13	0.0156 (13)	0.045 (2)	0.0266 (14)	0.0033 (13)	−0.0003 (11)	0.0033 (14)
C14	0.0276 (16)	0.0415 (19)	0.0209 (13)	−0.0006 (14)	0.0018 (11)	0.0002 (13)
C15	0.0260 (15)	0.0366 (18)	0.0233 (13)	0.0043 (13)	0.0104 (11)	0.0026 (13)
C16	0.0174 (13)	0.0252 (16)	0.0254 (13)	0.0055 (11)	0.0059 (10)	0.0057 (12)

Br1—C7	1.978 (3)	C14—C15	1.387 (4)
Br2—C8	1.974 (3)	C15—C16	1.387 (4)
C1—C2	1.405 (4)	C3—H3	0.9500
C1—C6	1.407 (4)	C4—H4	0.9500
C1—C11	1.486 (4)	C6—H6	0.9500
C2—C3	1.400 (4)	C7—H7A	0.9900
C2—C7	1.487 (4)	C7—H7B	0.9900
C3—C4	1.379 (4)	C8—H8A	0.9900
C4—C5	1.392 (4)	C8—H8B	0.9900
C5—C6	1.387 (4)	C12—H12	0.9500
C5—C8	1.495 (4)	C13—H13	0.9500
C11—C16	1.398 (4)	C14—H14	0.9500
C11—C12	1.400 (4)	C15—H15	0.9500
C12—C13	1.381 (4)	C16—H16	0.9500
C13—C14	1.395 (4)
C2—C1—C6	118.5 (2)	C3—C4—H4	120.0
C2—C1—C11	123.1 (2)	C5—C4—H4	120.0
C6—C1—C11	118.4 (2)	C5—C6—H6	119.0
C3—C2—C1	118.9 (2)	C1—C6—H6	119.0
C3—C2—C7	118.3 (2)	C2—C7—H7A	109.4
C1—C2—C7	122.7 (2)	Br1—C7—H7A	109.4
C4—C3—C2	121.7 (3)	C2—C7—H7B	109.4
C3—C4—C5	120.0 (3)	Br1—C7—H7B	109.4
C6—C5—C4	119.0 (3)	H7A—C7—H7B	108.0
C6—C5—C8	120.6 (3)	C5—C8—H8A	109.4
C4—C5—C8	120.4 (3)	Br2—C8—H8A	109.4
C5—C6—C1	121.9 (3)	C5—C8—H8B	109.4
C2—C7—Br1	111.0 (2)	Br2—C8—H8B	109.4
C5—C8—Br2	111.4 (2)	H8A—C8—H8B	108.0
C16—C11—C12	118.3 (3)	C13—C12—H12	119.7
C16—C11—C1	119.7 (2)	C11—C12—H12	119.7
C12—C11—C1	121.9 (2)	C12—C13—H13	119.7
C13—C12—C11	120.6 (3)	C14—C13—H13	119.7
C12—C13—C14	120.6 (3)	C15—C14—H14	120.4
C15—C14—C13	119.3 (3)	C13—C14—H14	120.4
C14—C15—C16	120.2 (3)	C14—C15—H15	119.9
C15—C16—C11	120.9 (3)	C16—C15—H15	119.9
C4—C3—H3	119.1	C15—C16—H16	119.5
C2—C3—H3	119.1	C11—C16—H16	119.5
C6—C1—C2—C3	0.2 (4)	C6—C5—C8—Br2	93.8 (3)
C11—C1—C2—C3	−179.4 (3)	C4—C5—C8—Br2	−87.9 (3)
C6—C1—C2—C7	175.8 (3)	C2—C1—C11—C16	128.0 (3)
C11—C1—C2—C7	−3.8 (4)	C6—C1—C11—C16	−51.6 (4)
C1—C2—C3—C4	−2.1 (4)	C2—C1—C11—C12	−53.6 (4)
C7—C2—C3—C4	−177.8 (3)	C6—C1—C11—C12	126.8 (3)
C2—C3—C4—C5	1.9 (4)	C16—C11—C12—C13	−1.6 (4)
C3—C4—C5—C6	0.1 (4)	C1—C11—C12—C13	179.9 (3)
C3—C4—C5—C8	−178.2 (3)	C11—C12—C13—C14	−1.0 (5)
C4—C5—C6—C1	−1.9 (4)	C12—C13—C14—C15	1.8 (5)
C8—C5—C6—C1	176.3 (3)	C13—C14—C15—C16	−0.1 (5)
C2—C1—C6—C5	1.8 (4)	C14—C15—C16—C11	−2.5 (5)
C11—C1—C6—C5	−178.6 (3)	C12—C11—C16—C15	3.3 (4)
C3—C2—C7—Br1	−77.2 (3)	C1—C11—C16—C15	−178.2 (3)
C1—C2—C7—Br1	107.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···Br1i	0.99	3.23	3.773 (3)	116
C12—H12···Br1ii	0.95	3.07	3.782 (3)	133
C13—H13···Br1ii	0.95	3.37	3.931 (3)	120
C13—H13···Br1iii	0.95	3.24	3.634 (3)	107
C14—H14···Br1iv	0.95	3.37	3.971 (3)	123
C14—H14···Br1v	0.95	3.43	4.326 (3)	157
C4—H4···Br2vi	0.95	3.37	4.260 (3)	156
C4—H4···Br2vii	0.95	3.26	3.845 (3)	122
C6—H6···Br2viii	0.95	3.20	4.124 (3)	166
C8—H8B···Br2ix	0.99	3.29	3.746 (3)	110
C8—H8A···Br2ix	0.99	3.43	3.746 (3)	101
C15—H15···Br2x	0.95	3.27	3.913 (3)	127
C16—H16···Br2viii	0.95	3.41	3.918 (3)	116
C16—H16···Br2x	0.95	3.24	3.898 (3)	128

Table 1

H⋯Br contacts (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯Br1i	0.99	3.23	3.773 (3)	116
C12—H12⋯Br1ii	0.95	3.07	3.782 (3)	133
C13—H13⋯Br1ii	0.95	3.37	3.931 (3)	120
C13—H13⋯Br1iii	0.95	3.24	3.634 (3)	107
C14—H14⋯Br1iv	0.95	3.37	3.971 (3)	123
C14—H14⋯Br1v	0.95	3.43	4.326 (3)	157
C4—H4⋯Br2vi	0.95	3.37	4.260 (3)	156
C4—H4⋯Br2vii	0.95	3.26	3.845 (3)	122
C6—H6⋯Br2viii	0.95	3.20	4.124 (3)	166
C8—H8B⋯Br2ix	0.99	3.29	3.746 (3)	110
C8—H8A⋯Br2ix	0.99	3.43	3.746 (3)	101
C15—H15⋯Br2x	0.95	3.27	3.913 (3)	127
C16—H16⋯Br2viii	0.95	3.41	3.918 (3)	116
C16—H16⋯Br2x	0.95	3.24	3.898 (3)	128

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) ; (x) .