2,3,4,5,6-Penta­bromo­phenyl phenyl ether

The title compound, C₁₂H₅Br₅O, belongs to a group of flame retardants known as polybrominated di­phenyl ethers (PBDE). Salient features of the packing are stabilization due to intermolecular Br...Br contacts in the ab plane and aromatic intermolecular contacts along the c direction.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.036
• wR factor = 0.066
• Data-to-parameter ratio = 17.4

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   0.114


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

2,3,4,5,6-Pentabromophenyl phenyl ether

Crystal data

C12H5Br5O	F(000) = 1040
Mr = 564.71	Dx = 2.582 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.579 (4) Å	Cell parameters from 1573 reflections
b = 5.3284 (11) Å	θ = 1.7–26.0°
c = 24.133 (6) Å	µ = 13.82 mm^−1
β = 102.66 (3)°	T = 293 K
V = 1452.7 (6) Å^3	Slab, colourless
Z = 4	0.30 × 0.09 × 0.08 mm

Data collection

STOE IPDS area-detector diffractometer	2843 independent reflections
Radiation source: fine-focus sealed tube	1503 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.114
Detector resolution: 6.0 pixels mm^-1	θmax = 26.0°, θmin = 2.2°
φ scans	h = −14→14
Absorption correction: numerical (X-RED; Stoe & Cie, 1997)	k = −6→6
Tmin = 0.081, Tmax = 0.328	l = −29→29
18710 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.066	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.005P)^2] where P = (Fo^2 + 2Fc^2)/3
2843 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.55 e Å^−3
46 restraints	Δρmin = −0.68 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	0.41828 (7)	−0.49976 (14)	0.39688 (4)	0.0702 (3)
Br2	0.43124 (8)	−0.14732 (16)	0.28503 (4)	0.0776 (3)
Br3	0.22400 (9)	0.27635 (13)	0.24144 (4)	0.0742 (3)
Br4	0.01204 (8)	0.35015 (13)	0.31134 (3)	0.0643 (2)
Br5	0.00287 (7)	−0.01692 (15)	0.42045 (4)	0.0643 (2)
O	0.2005 (4)	−0.3910 (7)	0.44035 (19)	0.0504 (12)
C1	0.2119 (6)	−0.2252 (10)	0.3984 (3)	0.0387 (15)
C2	0.3031 (6)	−0.2569 (10)	0.3708 (3)	0.0437 (16)
C3	0.3068 (6)	−0.1071 (12)	0.3242 (3)	0.0474 (17)
C4	0.2189 (6)	0.0720 (10)	0.3044 (3)	0.0444 (16)
C5	0.1298 (6)	0.1052 (10)	0.3346 (3)	0.0417 (16)
C6	0.1252 (6)	−0.0476 (10)	0.3811 (3)	0.0377 (15)
C7	0.2418 (6)	−0.3206 (11)	0.4973 (3)	0.0424 (16)
C8	0.2054 (6)	−0.4716 (12)	0.5368 (3)	0.0526 (18)
H8	0.1563	−0.6085	0.5250	0.063*
C9	0.2420 (7)	−0.4186 (15)	0.5935 (4)	0.068 (2)
H9	0.2184	−0.5210	0.6202	0.082*
C10	0.3125 (7)	−0.2173 (14)	0.6109 (3)	0.063 (2)
H10	0.3371	−0.1821	0.6494	0.076*
C11	0.3474 (7)	−0.0657 (13)	0.5715 (3)	0.065 (2)
H11	0.3947	0.0735	0.5835	0.078*
C12	0.3126 (7)	−0.1186 (12)	0.5140 (3)	0.0561 (19)
H12	0.3372	−0.0177	0.4873	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0518 (5)	0.0524 (4)	0.0998 (7)	0.0107 (4)	0.0024 (5)	−0.0123 (4)
Br2	0.0648 (6)	0.0970 (6)	0.0841 (7)	−0.0227 (5)	0.0449 (5)	−0.0308 (5)
Br3	0.1041 (8)	0.0737 (5)	0.0446 (5)	−0.0332 (5)	0.0159 (4)	0.0063 (4)
Br4	0.0692 (6)	0.0520 (4)	0.0611 (5)	0.0118 (4)	−0.0088 (4)	−0.0021 (4)
Br5	0.0529 (5)	0.0799 (5)	0.0671 (5)	0.0038 (4)	0.0282 (4)	−0.0030 (5)
O	0.068 (4)	0.036 (2)	0.045 (3)	−0.012 (2)	0.010 (3)	0.003 (2)
C1	0.049 (4)	0.036 (3)	0.031 (4)	−0.001 (3)	0.007 (3)	0.001 (3)
C2	0.043 (4)	0.033 (3)	0.055 (4)	0.005 (3)	0.010 (4)	−0.011 (3)
C3	0.051 (5)	0.050 (4)	0.045 (4)	−0.013 (3)	0.019 (4)	−0.021 (3)
C4	0.047 (4)	0.044 (4)	0.042 (4)	−0.013 (3)	0.012 (3)	−0.009 (3)
C5	0.047 (4)	0.029 (3)	0.044 (4)	−0.002 (3)	−0.002 (3)	−0.007 (3)
C6	0.037 (4)	0.036 (3)	0.040 (4)	−0.003 (3)	0.008 (3)	−0.005 (3)
C7	0.045 (4)	0.040 (4)	0.041 (4)	0.005 (3)	0.007 (3)	0.008 (3)
C8	0.059 (5)	0.049 (4)	0.052 (5)	0.001 (3)	0.018 (4)	0.007 (4)
C9	0.069 (6)	0.087 (6)	0.052 (5)	0.011 (4)	0.021 (5)	0.016 (4)
C10	0.061 (6)	0.076 (5)	0.049 (5)	0.026 (4)	0.007 (4)	−0.007 (4)
C11	0.068 (6)	0.063 (5)	0.056 (5)	0.000 (4)	−0.007 (4)	−0.010 (4)
C12	0.063 (5)	0.051 (4)	0.049 (5)	−0.011 (4)	0.001 (4)	0.004 (3)

Geometric parameters (Å, º)

Br1—C2	1.866 (6)	C3—C4	1.401 (9)
Br2—C3	1.900 (6)	C4—C5	1.400 (9)
Br3—C4	1.880 (6)	C5—C6	1.397 (8)
Br4—C5	1.882 (6)	C7—C12	1.359 (8)
Br5—C6	1.876 (6)	C7—C8	1.383 (8)
O—C1	1.371 (7)	C8—C9	1.369 (10)
O—C7	1.403 (8)	C9—C10	1.358 (10)
C1—C2	1.377 (8)	C10—C11	1.375 (10)
C1—C6	1.377 (8)	C11—C12	1.387 (10)
C2—C3	1.388 (9)
C1—O—C7	118.9 (4)	C6—C5—Br4	119.4 (5)
O—C1—C2	119.1 (5)	C4—C5—Br4	120.0 (5)
O—C1—C6	119.0 (6)	C1—C6—C5	119.4 (6)
C2—C1—C6	121.6 (6)	C1—C6—Br5	119.2 (4)
C1—C2—C3	119.0 (6)	C5—C6—Br5	121.4 (5)
C1—C2—Br1	119.3 (5)	C12—C7—C8	120.8 (6)
C3—C2—Br1	121.7 (5)	C12—C7—O	123.8 (6)
C2—C3—C4	121.3 (6)	C8—C7—O	115.5 (6)
C2—C3—Br2	120.0 (5)	C9—C8—C7	119.6 (7)
C4—C3—Br2	118.7 (5)	C10—C9—C8	120.4 (7)
C5—C4—C3	118.1 (6)	C9—C10—C11	119.9 (8)
C5—C4—Br3	120.3 (5)	C10—C11—C12	120.5 (7)
C3—C4—Br3	121.4 (5)	C7—C12—C11	118.8 (7)
C6—C5—C4	120.5 (6)
C7—O—C1—C2	100.4 (7)	O—C1—C6—C5	−173.5 (5)
C7—O—C1—C6	−86.2 (7)	C2—C1—C6—C5	−0.3 (9)
O—C1—C2—C3	172.7 (5)	O—C1—C6—Br5	6.3 (8)
C6—C1—C2—C3	−0.5 (9)	C2—C1—C6—Br5	179.5 (5)
O—C1—C2—Br1	−7.2 (8)	C4—C5—C6—C1	2.6 (9)
C6—C1—C2—Br1	179.6 (5)	Br4—C5—C6—C1	−179.4 (5)
C1—C2—C3—C4	−0.9 (9)	C4—C5—C6—Br5	−177.2 (5)
Br1—C2—C3—C4	179.0 (5)	Br4—C5—C6—Br5	0.8 (7)
C1—C2—C3—Br2	−179.8 (5)	C1—O—C7—C12	−12.9 (9)
Br1—C2—C3—Br2	0.1 (7)	C1—O—C7—C8	166.8 (5)
C2—C3—C4—C5	3.1 (9)	C12—C7—C8—C9	−0.7 (10)
Br2—C3—C4—C5	−178.0 (4)	O—C7—C8—C9	179.6 (6)
C2—C3—C4—Br3	179.7 (5)	C7—C8—C9—C10	0.8 (11)
Br2—C3—C4—Br3	−1.5 (7)	C8—C9—C10—C11	0.0 (11)
C3—C4—C5—C6	−3.9 (9)	C9—C10—C11—C12	−0.9 (11)
Br3—C4—C5—C6	179.5 (4)	C8—C7—C12—C11	−0.2 (10)
C3—C4—C5—Br4	178.1 (4)	O—C7—C12—C11	179.5 (6)
Br3—C4—C5—Br4	1.5 (7)	C10—C11—C12—C7	1.0 (11)