3,9-Dibromo-5,7-dihydro-dibenzo[c,e]oxepine.

The title compound, C(14)H(10)Br(2)O, is a biphenyl derivative containing a -CH(2)-O-CH(2)- bridge in the 2,2'-position. The compound displays a twisted conformation with the two benzene rings making a dihedral angle of 45.02 (5)°, while the central seven-membered ring is in a boat conformation. The mol-ecule lies on a crystallographic twofold axis of symmetry passing through the O atom and bis-ecting the 1,1' C-C bond.

Related literature

For a previous synthesis of related biphenyl mol­ecules, see: Mislow & Glass (1961 ▶).

Experimental

Crystal data

C14H10Br2O

M = 354.04

Orthorhombic,

a = 16.5965 (3) Å

b = 10.2476 (6) Å

c = 7.2626 (14) Å

V = 1235.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 6.54 mm−1

T = 291 (2) K

0.14 × 0.14 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.457, T max = 0.498 (expected range = 0.419–0.456)

2468 measured reflections

1371 independent reflections

896 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.042

S = 1.05

1371 reflections

78 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.46 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808018175/bv2098sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018175/bv2098Isup2.hkl

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

C14H10Br2O	F000 = 688
Mr = 354.04	Dx = 1.904 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 10356 reflections
a = 16.5965 (3) Å	θ = 2.5–54.9º
b = 10.2476 (6) Å	µ = 6.54 mm−1
c = 7.2626 (14) Å	T = 291 (2) K
V = 1235.2 (2) Å3	Block, colorless
Z = 4	0.14 × 0.14 × 0.12 mm

Rigaku R-AXIS RAPID diffractometer	1371 independent reflections
Radiation source: fine-focus sealed tube	896 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.014
T = 291(2) K	θmax = 27.5º
ω scans	θmin = 2.3º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	h = −21→21
Tmin = 0.457, Tmax = 0.498	k = −13→12
2468 measured reflections	l = −9→9

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)] = 0.024	H-atom parameters constrained
wR(F2) = 0.042	w = 1/[σ2(Fo2) + (0.0103P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1371 reflections	Δρmax = 0.28 e Å−3
78 parameters	Δρmin = −0.46 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.677363 (15)	0.36711 (3)	0.14224 (4)	0.04966 (11)
O1	1.0000	0.0746 (2)	0.2500	0.0401 (7)
C1	0.79077 (14)	0.3698 (3)	0.1813 (3)	0.0333 (6)
C6	0.82561 (17)	0.4814 (3)	0.2538 (3)	0.0392 (7)
H6A	0.7943	0.5534	0.2846	0.047*
C3	0.91882 (13)	0.2642 (2)	0.1600 (3)	0.0251 (5)
C7	0.96934 (14)	0.1504 (2)	0.1017 (3)	0.0342 (6)
H7A	0.9373	0.0944	0.0228	0.041*
H7B	1.0143	0.1825	0.0293	0.041*
C4	0.95561 (13)	0.3761 (2)	0.2353 (3)	0.0273 (5)
C2	0.83600 (13)	0.2626 (2)	0.1339 (3)	0.0295 (6)
H2A	0.8112	0.1891	0.0845	0.035*
C5	0.90852 (16)	0.4830 (3)	0.2793 (3)	0.0361 (7)
H5A	0.9329	0.5574	0.3270	0.043*

	U11	U22	U33	U12	U13	U23
Br1	0.03162 (14)	0.0648 (2)	0.05259 (17)	0.01473 (19)	−0.00240 (17)	0.0052 (2)
O1	0.0350 (15)	0.0224 (14)	0.0629 (18)	0.000	−0.0084 (15)	0.000
C1	0.0301 (13)	0.0443 (16)	0.0257 (13)	0.0091 (16)	0.0001 (11)	0.0004 (15)
C6	0.0487 (17)	0.0390 (16)	0.0299 (13)	0.0231 (19)	−0.0067 (15)	−0.0083 (12)
C3	0.0245 (13)	0.0250 (13)	0.0260 (12)	0.0011 (12)	0.0036 (13)	0.0030 (12)
C7	0.0270 (13)	0.0304 (15)	0.0452 (16)	−0.0031 (13)	0.0024 (12)	−0.0083 (12)
C4	0.0331 (13)	0.0259 (13)	0.0230 (11)	0.0045 (14)	−0.0011 (12)	0.0022 (12)
C2	0.0321 (15)	0.0282 (13)	0.0283 (12)	0.0001 (12)	0.0023 (15)	−0.0005 (12)
C5	0.0489 (18)	0.0275 (15)	0.0321 (13)	0.0069 (16)	−0.0108 (14)	−0.0061 (12)

Br1—C1	1.904 (2)	C3—C4	1.410 (3)
O1—C7i	1.422 (3)	C3—C7	1.497 (3)
O1—C7	1.422 (3)	C7—H7A	0.9700
C1—C2	1.375 (3)	C7—H7B	0.9700
C1—C6	1.386 (3)	C4—C5	1.383 (3)
C6—C5	1.389 (3)	C4—C4i	1.489 (4)
C6—H6A	0.9300	C2—H2A	0.9300
C3—C2	1.388 (3)	C5—H5A	0.9300
C7i—O1—C7	113.8 (2)	O1—C7—H7B	108.7
C2—C1—C6	121.8 (2)	C3—C7—H7B	108.7
C2—C1—Br1	119.40 (19)	H7A—C7—H7B	107.6
C6—C1—Br1	118.8 (2)	C5—C4—C3	119.3 (2)
C1—C6—C5	118.3 (2)	C5—C4—C4i	121.75 (17)
C1—C6—H6A	120.9	C3—C4—C4i	118.96 (16)
C5—C6—H6A	120.9	C1—C2—C3	119.8 (2)
C2—C3—C4	119.5 (2)	C1—C2—H2A	120.1
C2—C3—C7	120.5 (2)	C3—C2—H2A	120.1
C4—C3—C7	120.0 (2)	C4—C5—C6	121.4 (3)
O1—C7—C3	114.29 (19)	C4—C5—H5A	119.3
O1—C7—H7A	108.7	C6—C5—H5A	119.3
C3—C7—H7A	108.7