4-Bromo­phenyl 2,4-di­bromo­phenyl ether

The title compound, C₁₂H₇Br₃O, belongs to a group of flame retardants known as polybrominated di­phenyl ethers (PBDE). Salient features of the packing of the title compound are infinite intermolecular Br...Br contact chains along the b direction.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.035
• wR factor = 0.044
• Data-to-parameter ratio = 17.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



RINTA_01  Alert C The value of Rint is greater than 0.10
          Rint given   0.103


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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Computing details

Data collection: EXPOSE in IPDS (Stoe, 1997); cell refinement: CELL in IPDS; data reduction: INTEGRATE in IPDS and X-RED (Stoe, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff, 1996).

2,4-Bibromophenyl 4-bromophenyl ether

Crystal data

C12H7Br3O	Dx = 2.092 Mg m^−3
Mr = 406.91	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 1235 reflections
a = 15.480 (3) Å	θ = 1.7–26.0°
b = 5.9692 (9) Å	µ = 9.34 mm^−1
c = 27.962 (5) Å	T = 293 K
V = 2583.7 (8) Å^3	Irregular, colourless
Z = 8	0.16 × 0.07 × 0.06 mm
F(000) = 1536

Data collection

Stoe IPDS area-detector diffractometer	2513 independent reflections
Radiation source: fine-focus sealed tube	1335 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.103
Detector resolution: 6.0 pixels mm^-1	θmax = 26.0°, θmin = 2.0°
area detector scans	h = −19→19
Absorption correction: numerical (XRED; Stoe & Cie, 1997)	k = −7→7
Tmin = 0.231, Tmax = 0.574	l = −34→34
36351 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.044	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.01P)^2] where P = (Fo^2 + 2Fc^2)/3
2513 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.53 e Å^−3
40 restraints	Δρmin = −0.41 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.64870 (3)	−0.19445 (13)	0.165844 (15)	0.0833 (2)
Br2	0.67846 (2)	0.17074 (10)	0.415110 (16)	0.06006 (14)
Br3	0.34387 (3)	0.32515 (11)	0.486260 (15)	0.06214 (16)
O	0.59364 (19)	−0.2643 (5)	0.37919 (10)	0.0590 (9)
C1	0.6023 (2)	−0.2375 (8)	0.33024 (14)	0.0447 (12)
C2	0.5668 (3)	−0.0669 (8)	0.30430 (16)	0.0560 (13)
H2	0.5330	0.0402	0.3196	0.067*
C3	0.5806 (3)	−0.0519 (8)	0.25538 (16)	0.0556 (13)
H3	0.5568	0.0657	0.2380	0.067*
C4	0.6295 (2)	−0.2111 (9)	0.23291 (14)	0.0508 (12)
C5	0.6660 (3)	−0.3846 (8)	0.25861 (15)	0.0587 (13)
H5	0.6994	−0.4923	0.2433	0.070*
C6	0.6522 (3)	−0.3965 (8)	0.30768 (15)	0.0542 (13)
H6	0.6768	−0.5122	0.3253	0.065*
C7	0.5366 (3)	−0.1259 (8)	0.40292 (13)	0.0467 (12)
C8	0.5628 (2)	0.0757 (8)	0.42236 (13)	0.0408 (11)
C9	0.5069 (2)	0.2116 (8)	0.44708 (12)	0.0384 (11)
H9	0.5251	0.3483	0.4594	0.046*
C10	0.4222 (2)	0.1388 (8)	0.45310 (13)	0.0411 (12)
C11	0.3956 (3)	−0.0634 (9)	0.43452 (15)	0.0537 (13)
H11	0.3388	−0.1103	0.4387	0.064*
C12	0.4526 (3)	−0.1959 (9)	0.40987 (15)	0.0557 (11)
H12	0.4347	−0.3334	0.3978	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0966 (4)	0.1040 (6)	0.0492 (3)	0.0095 (5)	0.0052 (3)	−0.0010 (3)
Br2	0.0372 (2)	0.0669 (3)	0.0761 (3)	0.0025 (3)	0.0028 (2)	0.0101 (3)
Br3	0.0481 (2)	0.0738 (4)	0.0645 (3)	0.0102 (3)	0.0116 (2)	0.0004 (3)
O	0.080 (2)	0.049 (3)	0.0477 (16)	0.0253 (17)	0.0002 (14)	0.0012 (16)
C1	0.047 (2)	0.045 (4)	0.043 (2)	0.007 (3)	−0.003 (2)	−0.004 (2)
C2	0.059 (3)	0.052 (4)	0.057 (3)	0.022 (3)	−0.004 (2)	−0.002 (3)
C3	0.058 (3)	0.054 (3)	0.054 (3)	0.014 (3)	−0.008 (2)	0.011 (3)
C4	0.041 (2)	0.052 (4)	0.059 (2)	0.001 (2)	−0.004 (2)	−0.009 (3)
C5	0.052 (3)	0.057 (4)	0.068 (3)	0.016 (3)	0.004 (2)	−0.009 (2)
C6	0.064 (3)	0.040 (4)	0.058 (3)	0.018 (3)	−0.010 (3)	0.007 (2)
C7	0.061 (3)	0.041 (4)	0.038 (2)	0.011 (2)	−0.001 (2)	0.004 (2)
C8	0.039 (2)	0.044 (3)	0.040 (3)	0.011 (2)	−0.0034 (19)	0.002 (2)
C9	0.040 (2)	0.032 (3)	0.043 (2)	0.003 (2)	−0.0067 (17)	−0.003 (2)
C10	0.038 (2)	0.048 (4)	0.038 (2)	−0.001 (2)	−0.0022 (17)	0.005 (2)
C11	0.043 (3)	0.059 (4)	0.059 (3)	−0.011 (3)	0.000 (2)	0.003 (3)
C12	0.064 (3)	0.044 (3)	0.058 (2)	−0.015 (3)	−0.007 (3)	−0.009 (3)

Geometric parameters (Å, º)

Br1—C4	1.901 (4)	C7—C8	1.381 (5)
Br2—C8	1.889 (4)	C8—C9	1.373 (5)
Br3—C10	1.889 (4)	C9—C10	1.391 (5)
O—C7	1.380 (5)	C10—C11	1.377 (6)
O—C1	1.385 (4)	C11—C12	1.371 (6)
C1—C2	1.365 (6)	C2—H2	0.9300
C1—C6	1.377 (6)	C3—H3	0.9300
C2—C3	1.387 (6)	C5—H5	0.9300
C3—C4	1.368 (6)	C6—H6	0.9300
C4—C5	1.381 (6)	C9—H9	0.9300
C5—C6	1.391 (5)	C11—H11	0.9300
C7—C12	1.378 (5)	C12—H12	0.9300
C7—O—C1	117.9 (3)	C11—C10—Br3	120.6 (3)
C2—C1—C6	119.8 (4)	C9—C10—Br3	118.7 (4)
C2—C1—O	124.9 (4)	C12—C11—C10	120.2 (4)
C6—C1—O	115.3 (4)	C11—C12—C7	120.2 (5)
C1—C2—C3	120.6 (4)	C1—C2—H2	119.7
C4—C3—C2	119.6 (4)	C3—C2—H2	119.7
C3—C4—C5	120.6 (4)	C4—C3—H3	120.2
C3—C4—Br1	120.2 (4)	C2—C3—H3	120.2
C5—C4—Br1	119.2 (3)	C4—C5—H5	120.4
C4—C5—C6	119.3 (4)	C6—C5—H5	120.4
C1—C6—C5	120.2 (4)	C1—C6—H6	119.9
C12—C7—O	119.3 (4)	C5—C6—H6	119.9
C12—C7—C8	119.0 (4)	C8—C9—H9	121.0
O—C7—C8	121.5 (4)	C10—C9—H9	121.0
C9—C8—C7	121.9 (4)	C12—C11—H11	119.9
C9—C8—Br2	118.3 (3)	C10—C11—H11	119.9
C7—C8—Br2	119.9 (3)	C11—C12—H12	119.9
C8—C9—C10	118.0 (4)	C7—C12—H12	119.9
C11—C10—C9	120.7 (4)
C7—O—C1—C2	8.5 (6)	C12—C7—C8—C9	−2.1 (6)
C7—O—C1—C6	−172.7 (4)	O—C7—C8—C9	−178.3 (3)
C6—C1—C2—C3	−0.1 (7)	C12—C7—C8—Br2	177.9 (3)
O—C1—C2—C3	178.7 (4)	O—C7—C8—Br2	1.8 (5)
C1—C2—C3—C4	0.7 (7)	C7—C8—C9—C10	1.3 (6)
C2—C3—C4—C5	−0.8 (6)	Br2—C8—C9—C10	−178.8 (3)
C2—C3—C4—Br1	179.6 (3)	C8—C9—C10—C11	−0.3 (6)
C3—C4—C5—C6	0.3 (6)	C8—C9—C10—Br3	−179.1 (3)
Br1—C4—C5—C6	179.8 (3)	C9—C10—C11—C12	0.1 (6)
C2—C1—C6—C5	−0.5 (7)	Br3—C10—C11—C12	179.0 (3)
O—C1—C6—C5	−179.3 (4)	C10—C11—C12—C7	−1.0 (7)
C4—C5—C6—C1	0.4 (6)	O—C7—C12—C11	178.2 (4)
C1—O—C7—C12	92.7 (5)	C8—C7—C12—C11	2.0 (6)
C1—O—C7—C8	−91.2 (5)