Decabromo­diphenyl­ethane

Decabromo­diphenyl­ethane [systematic name: 1,1′-ethane-1,2-diylbis(penta­bromo­benzene)], C₁₄H₄Br₁₀ (DBDPE), was crystallized from toluene. The mol­ecule shows crystallographic inversion symmetry. The C—Br distances are in the range 1.873 (7)–1.891 (6) Å; inter­molecular Br...Br contacts contribute to the formation of ribbons.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.043
• wR factor = 0.121
• Data-to-parameter ratio = 20.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.07
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and SHELXTL (Bruker 1997); software used to prepare material for publication: SHELXL97.

1,1'-ethane-1,2-diylbis(pentabromobenzene)

Crystal data

C14H4Br10	Z = 1
Mr = 971.17	F(000) = 438
Triclinic, P1	Dx = 3.264 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.864 (5) Å	Cell parameters from 128 reflections
b = 7.970 (4) Å	θ = 3.5–29.6°
c = 9.116 (5) Å	µ = 20.27 mm^−1
α = 94.095 (7)°	T = 273 K
β = 107.198 (8)°	Block, colourless
γ = 112.263 (8)°	0.12 × 0.10 × 0.10 mm
V = 494.1 (5) Å^3

Data collection

Bruker APEX CCD area-detector diffractometer	2247 independent reflections
Radiation source: fine-focus sealed tube	1491 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scan	θmax = 27.6°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −10→8
Tmin = 0.108, Tmax = 0.132	k = −6→10
3366 measured reflections	l = −11→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.0562P)^2 + 1.2587P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
2247 reflections	Δρmax = 0.94 e Å^−3
110 parameters	Δρmin = −0.97 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0022 (6)

Special details

Experimental. IR (KBr, pellet, cm^-1): 2976.7, 2950.7, 2945.4, 2867.2, 2780.9, 2716.0, 2704.3, 1509.8, 1449.6, 1392.8, 1322.4, 1313.4, 1284.3, 1228.4, 1179.3, 1140.9, 1058.0, 882.8, 764.4, 662.7, 555.9

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.

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

	x	y	z	Uiso*/Ueq
Br1	0.46511 (15)	0.32632 (11)	0.13937 (10)	0.0500 (3)
Br2	0.17999 (14)	−0.10536 (11)	−0.02084 (9)	0.0453 (3)
Br3	−0.00682 (13)	−0.39108 (10)	0.18809 (10)	0.0449 (3)
Br4	0.09457 (12)	−0.23991 (10)	0.56051 (9)	0.0396 (3)
Br5	0.38625 (13)	0.19002 (10)	0.72440 (9)	0.0417 (3)
C1	0.5504 (10)	0.4370 (9)	0.5009 (9)	0.0291 (17)
H1	0.6440	0.4814	0.4477	0.035*
H2	0.6232	0.4424	0.6089	0.035*
C2	0.4101 (9)	0.2353 (8)	0.4226 (8)	0.0247 (15)
C4	0.2353 (10)	−0.0195 (9)	0.1926 (8)	0.0273 (16)
C5	0.1571 (10)	−0.1398 (9)	0.2812 (8)	0.0267 (16)
C7	0.3282 (10)	0.1096 (9)	0.5100 (8)	0.0265 (16)
C3	0.3625 (11)	0.1659 (9)	0.2634 (8)	0.0270 (16)
C6	0.2010 (10)	−0.0748 (9)	0.4392 (8)	0.0249 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0767 (7)	0.0294 (4)	0.0382 (5)	0.0079 (4)	0.0304 (5)	0.0099 (3)
Br2	0.0676 (6)	0.0345 (5)	0.0263 (4)	0.0137 (4)	0.0178 (4)	0.0007 (3)
Br3	0.0558 (6)	0.0217 (4)	0.0388 (5)	0.0014 (3)	0.0125 (4)	−0.0012 (3)
Br4	0.0522 (5)	0.0267 (4)	0.0382 (5)	0.0086 (3)	0.0225 (4)	0.0124 (3)
Br5	0.0640 (6)	0.0299 (4)	0.0257 (4)	0.0134 (4)	0.0170 (4)	0.0037 (3)
C1	0.029 (4)	0.021 (3)	0.029 (4)	0.004 (3)	0.008 (3)	0.004 (3)
C2	0.025 (4)	0.017 (3)	0.028 (4)	0.003 (3)	0.011 (3)	−0.002 (3)
C4	0.033 (4)	0.027 (4)	0.024 (4)	0.016 (3)	0.010 (3)	0.001 (3)
C5	0.028 (4)	0.018 (3)	0.032 (4)	0.008 (3)	0.009 (3)	0.002 (3)
C7	0.033 (4)	0.023 (3)	0.023 (3)	0.012 (3)	0.008 (3)	0.002 (3)
C3	0.038 (4)	0.021 (3)	0.028 (4)	0.013 (3)	0.018 (3)	0.008 (3)
C6	0.028 (4)	0.019 (3)	0.030 (4)	0.010 (3)	0.013 (3)	0.006 (3)

Geometric parameters (Å, º)

Br1—C3	1.879 (6)	C2—C7	1.408 (9)
Br2—C4	1.878 (7)	C4—C3	1.401 (9)
Br3—C5	1.884 (7)	C4—C5	1.382 (9)
Br4—C6	1.891 (6)	C5—C6	1.387 (10)
Br5—C7	1.873 (7)	C7—C6	1.395 (9)
C1—C2	1.529 (9)	Br1—H1	2.694
C1—C1^i	1.495 (15)	Br5—H2	2.692
C2—C3	1.400 (9)
C2—C1—C1^i	113.6 (7)	C2—C7—Br5	120.0 (5)
C3—C2—C7	117.1 (6)	C4—C3—C2	121.7 (6)
C3—C2—C1	121.9 (6)	C4—C3—Br1	118.9 (5)
C7—C2—C1	120.9 (6)	C2—C3—Br1	119.4 (5)
C3—C4—C5	119.9 (6)	C7—C6—C5	120.5 (6)
C3—C4—Br2	119.7 (5)	C7—C6—Br4	119.9 (5)
C5—C4—Br2	120.3 (5)	C5—C6—Br4	119.6 (5)
C4—C5—C6	119.7 (6)	Br1—H1—C1	109.2
C4—C5—Br3	120.0 (5)	Br1—H1—C1	109.1
C6—C5—Br3	120.3 (5)	C3—Br1—H1	68.2
C6—C7—C2	121.1 (6)	C7—Br5—H2	68.1
C6—C7—Br5	118.9 (5)

Symmetry code: (i) −x+1, −y+1, −z+1.