1,4-Bis(bromo­meth­yl)benzene

In the title compound, C₈H₈Br₂, the mol­ecules are located on inversion centres and are connected through weak inter­molecular Br...Br inter­actions into layers parallel to the (102) plane.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.047
• wR factor = 0.149
• Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.20 Ratio

   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
   0 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
   1 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, 2001); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

1,4-Bis(bromomethyl)benzene

Crystal data

C8H8Br2	F(000) = 252
Mr = 263.96	Dx = 2.027 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1976 reflections
a = 8.7424 (7) Å	θ = 2.4–28.0°
b = 4.6275 (4) Å	µ = 9.30 mm^−1
c = 10.8189 (9) Å	T = 297 K
β = 98.885 (1)°	Plate, colourless
V = 432.43 (6) Å^3	0.30 × 0.30 × 0.20 mm
Z = 2

Data collection

Bruker SMART APEX CCD area-detector diffractometer	848 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	712 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
0.3° wide ω exposures scans	θmax = 26.0°, θmin = 3.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.082, Tmax = 0.157	k = −5→5
3213 measured reflections	l = −13→13

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.149	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.1099P)^2] where P = (Fo^2 + 2Fc^2)/3
848 reflections	(Δ/σ)max < 0.001
46 parameters	Δρmax = 0.77 e Å^−3
0 restraints	Δρmin = −0.85 e Å^−3

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

	x	y	z	Uiso*/Ueq
Br1	0.12045 (5)	0.07974 (12)	0.16966 (4)	0.0578 (4)
C1	0.3699 (5)	0.1456 (10)	0.0280 (4)	0.0435 (10)
C2	0.5155 (6)	0.1886 (11)	0.1000 (5)	0.0493 (11)
H2	0.5257	0.3154	0.1675	0.059*
C3	0.6432 (6)	0.0451 (11)	0.0720 (5)	0.0511 (12)
H3	0.7393	0.0760	0.1205	0.061*
C4	0.2306 (7)	0.3049 (12)	0.0570 (6)	0.0585 (13)
H4A	0.1613	0.3442	−0.0202	0.070*
H4B	0.2627	0.4885	0.0959	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0532 (5)	0.0686 (5)	0.0573 (5)	−0.0004 (2)	0.0272 (3)	−0.00340 (19)
C1	0.044 (3)	0.041 (2)	0.049 (2)	0.0051 (19)	0.022 (2)	0.0073 (18)
C2	0.054 (3)	0.049 (2)	0.049 (2)	−0.001 (2)	0.019 (2)	−0.005 (2)
C3	0.048 (3)	0.056 (3)	0.051 (3)	−0.002 (2)	0.013 (2)	0.002 (2)
C4	0.053 (3)	0.050 (3)	0.079 (3)	0.008 (2)	0.031 (3)	0.010 (3)

Geometric parameters (Å, º)

Br1—C4	1.965 (6)	C2—H2	0.9300
C1—C3^i	1.387 (7)	C3—C1^i	1.387 (7)
C1—C2	1.400 (7)	C3—H3	0.9300
C1—C4	1.498 (7)	C4—H4A	0.9700
C2—C3	1.372 (7)	C4—H4B	0.9700
C3^i—C1—C2	118.9 (4)	C1^i—C3—H3	119.7
C3^i—C1—C4	120.3 (5)	C1—C4—Br1	111.2 (3)
C2—C1—C4	120.8 (4)	C1—C4—H4A	109.4
C3—C2—C1	120.6 (5)	Br1—C4—H4A	109.4
C3—C2—H2	119.7	C1—C4—H4B	109.4
C1—C2—H2	119.7	Br1—C4—H4B	109.4
C2—C3—C1^i	120.5 (5)	H4A—C4—H4B	108.0
C2—C3—H3	119.7
C3^i—C1—C2—C3	0.2 (8)	C3^i—C1—C4—Br1	88.2 (5)
C4—C1—C2—C3	−179.1 (5)	C2—C1—C4—Br1	−92.5 (5)
C1—C2—C3—C1^i	−0.2 (8)

Symmetry code: (i) −x+1, −y, −z.