Bis(2-bromo-5-methyl-phen-oxy)methane.

The complete mol-ecule of the title compund, C(15)H(14)Br(2)O(2), is generated by the application of crystallographic twofold symmetry, with the central C atom lying on the rotation axis. The dihedral angle between the benzene rings is 62.4 (3)°. In the crystal, short Br⋯Br contacts [3.4885 (16) Å] occur.

Related literature

For background to bromo­aromatic compounds, see: Butler & Walker (1993 ▶); Seevers & Counsell (1982 ▶). For a related structure, see: Zheng et al. (2004 ▶).

Experimental

Crystal data

C15H14Br2O2

M = 386.08

Orthorhombic,

a = 10.7752 (11) Å

b = 15.8690 (17) Å

c = 4.3272 (10) Å

V = 739.9 (2) Å3

Z = 2

Cu Kα radiation

μ = 6.91 mm−1

T = 291 K

0.35 × 0.30 × 0.30 mm

Data collection

Agilent Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.196, T max = 0.231

1505 measured reflections

1022 independent reflections

754 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.123

S = 1.02

1022 reflections

88 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.41 e Å−3

Absolute structure: Flack (1983 ▶), 212 Friedel pairs

Flack parameter: −0.11 (9)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811034805/hb6383sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034805/hb6383Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034805/hb6383Isup3.cml

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

C15H14Br2O2	Dx = 1.733 Mg m−3
Mr = 386.08	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P21212	Cell parameters from 443 reflections
a = 10.7752 (11) Å	θ = 4.1–69.9°
b = 15.8690 (17) Å	µ = 6.91 mm−1
c = 4.3272 (10) Å	T = 291 K
V = 739.9 (2) Å3	Prism, colorless
Z = 2	0.35 × 0.30 × 0.30 mm
F(000) = 380

Agilent Xcalibur Eos Gemini diffractometer	1022 independent reflections
Radiation source: fine-focus sealed tube	754 reflections with I > 2σ(I)
graphite	Rint = 0.044
Detector resolution: 16.2312 pixels mm-1	θmax = 66.9°, θmin = 5.0°
ω scans	h = −12→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −18→14
Tmin = 0.196, Tmax = 0.231	l = −3→4
1505 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.040P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
1022 reflections	Δρmax = 0.36 e Å−3
88 parameters	Δρmin = −0.41 e Å−3
0 restraints	Absolute structure: Flack (1983), 212 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.11 (9)

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	Occ. (<1)
Br1	0.85154 (9)	0.95619 (6)	0.6233 (4)	0.0946 (6)
O1	0.6042 (5)	0.9803 (3)	0.3521 (17)	0.0668 (18)
C1	0.7175 (7)	0.8802 (4)	0.624 (3)	0.054 (2)
C2	0.6083 (7)	0.9029 (5)	0.489 (2)	0.056 (3)
C3	0.5091 (8)	0.8444 (5)	0.500 (2)	0.066 (3)
H3	0.4330	0.8573	0.4098	0.079*
C4	0.5267 (8)	0.7679 (5)	0.646 (3)	0.070 (3)
H4	0.4617	0.7294	0.6501	0.084*
C5	0.6369 (8)	0.7465 (4)	0.787 (2)	0.060 (3)
C6	0.7312 (8)	0.8044 (5)	0.779 (2)	0.058 (3)
H6	0.8056	0.7925	0.8792	0.069*
C7	0.6509 (9)	0.6621 (5)	0.946 (2)	0.090 (3)
H7A	0.7023	0.6684	1.1261	0.135*
H7B	0.6886	0.6226	0.8070	0.135*
H7C	0.5706	0.6417	1.0072	0.135*
C8	0.5000	1.0000	0.168 (4)	0.080 (5)
H8A	0.4805	0.9524	0.0361	0.096*	0.50
H8B	0.5195	1.0476	0.0361	0.096*	0.50

	U11	U22	U33	U12	U13	U23
Br1	0.0546 (6)	0.0668 (6)	0.1623 (14)	−0.0129 (5)	−0.0131 (8)	0.0130 (8)
O1	0.049 (3)	0.062 (3)	0.089 (5)	0.017 (3)	0.004 (4)	0.012 (4)
C1	0.052 (4)	0.042 (4)	0.066 (7)	0.009 (3)	0.001 (5)	0.004 (5)
C2	0.048 (4)	0.056 (5)	0.062 (8)	0.020 (4)	0.010 (5)	−0.001 (5)
C3	0.043 (4)	0.081 (6)	0.074 (8)	0.006 (5)	−0.009 (5)	−0.012 (6)
C4	0.058 (5)	0.061 (5)	0.090 (9)	−0.011 (4)	0.009 (7)	−0.008 (7)
C5	0.064 (5)	0.041 (4)	0.074 (8)	−0.006 (4)	0.020 (5)	−0.001 (5)
C6	0.058 (5)	0.057 (5)	0.058 (7)	0.008 (4)	0.007 (5)	0.002 (5)
C7	0.110 (8)	0.062 (5)	0.098 (9)	−0.002 (6)	0.019 (9)	0.026 (6)
C8	0.082 (10)	0.077 (9)	0.081 (12)	0.023 (8)	0.000	0.000

Br1—C1	1.882 (7)	C5—C6	1.370 (10)
O1—C2	1.364 (9)	C5—C7	1.515 (10)
O1—C8	1.412 (10)	C6—H6	0.9300
C1—C2	1.363 (11)	C7—H7A	0.9600
C1—C6	1.385 (10)	C7—H7B	0.9600
C2—C3	1.417 (11)	C7—H7C	0.9600
C3—C4	1.383 (11)	C8—O1i	1.412 (10)
C3—H3	0.9300	C8—H8A	0.9700
C4—C5	1.376 (12)	C8—H8B	0.9700
C4—H4	0.9300
C2—O1—C8	118.0 (6)	C5—C6—C1	121.0 (8)
C2—C1—C6	122.1 (7)	C5—C6—H6	119.5
C2—C1—Br1	119.4 (6)	C1—C6—H6	119.5
C6—C1—Br1	118.4 (6)	C5—C7—H7A	109.5
C1—C2—O1	117.0 (7)	C5—C7—H7B	109.5
C1—C2—C3	117.6 (8)	H7A—C7—H7B	109.5
O1—C2—C3	125.5 (8)	C5—C7—H7C	109.5
C4—C3—C2	119.2 (8)	H7A—C7—H7C	109.5
C4—C3—H3	120.4	H7B—C7—H7C	109.5
C2—C3—H3	120.4	O1—C8—O1i	111.2 (12)
C5—C4—C3	122.5 (8)	O1—C8—H8A	109.4
C5—C4—H4	118.7	O1i—C8—H8A	109.4
C3—C4—H4	118.7	O1—C8—H8B	109.4
C6—C5—C4	117.6 (8)	O1i—C8—H8B	109.4
C6—C5—C7	122.0 (9)	H8A—C8—H8B	108.0
C4—C5—C7	120.3 (8)
C6—C1—C2—O1	177.7 (8)	C2—C3—C4—C5	1.0 (16)
Br1—C1—C2—O1	1.3 (13)	C3—C4—C5—C6	0.2 (16)
C6—C1—C2—C3	−2.4 (15)	C3—C4—C5—C7	179.6 (9)
Br1—C1—C2—C3	−178.8 (7)	C4—C5—C6—C1	−2.5 (15)
C8—O1—C2—C1	170.0 (9)	C7—C5—C6—C1	178.1 (8)
C8—O1—C2—C3	−9.8 (14)	C2—C1—C6—C5	3.7 (15)
C1—C2—C3—C4	0.1 (15)	Br1—C1—C6—C5	−179.8 (7)
O1—C2—C3—C4	179.9 (9)	C2—O1—C8—O1i	76.7 (6)