1,2,4,5-Tetra­kis(bromo­meth­yl)benzene

The title mol­ecule, C₁₀H₁₀Br₄, lies on a crystallographic inversion center which is located at the center of the benzene ring. The crystal structure is stabilized by inter­molecular Br...Br and C—H...Br inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.037
• wR factor = 0.097
• Data-to-parameter ratio = 21.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.80
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.41
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.14
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  Br2     ..       3.52 Ang.
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.14 Ratio

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.412
            Tmax scaled      0.075 Tmin scaled      0.075

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 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: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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.

1,2,4,5-tetrakis(bromomethyl)benzene

Crystal data

C10H10Br4	F(000) = 420
Mr = 449.82	Dx = 2.417 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1394 reflections
a = 6.9695 (14) Å	θ = 3.0–27.1°
b = 9.880 (2) Å	µ = 12.98 mm^−1
c = 9.2352 (19) Å	T = 298 K
β = 103.638 (4)°	Block, colourless
V = 618.0 (2) Å^3	0.20 × 0.20 × 0.20 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	1343 independent reflections
Radiation source: fine-focus sealed tube	1067 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 27.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −8→8
Tmin = 0.181, Tmax = 0.181	k = −11→12
3526 measured reflections	l = −6→11

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.045P)^2 + 0.7024P] where P = (Fo^2 + 2Fc^2)/3
1343 reflections	(Δ/σ)max = 0.001
64 parameters	Δρmax = 0.57 e Å^−3
0 restraints	Δρmin = −0.61 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	0.27950 (9)	0.86420 (5)	1.00357 (6)	0.0482 (2)
Br2	−0.27607 (9)	0.83080 (5)	0.79953 (6)	0.0496 (2)
C1	0.1369 (7)	0.5903 (4)	0.9656 (5)	0.0316 (10)
C2	−0.0561 (7)	0.5880 (4)	0.8778 (5)	0.0314 (10)
C3	0.1882 (7)	0.5028 (4)	1.0863 (5)	0.0321 (10)
H3	0.3163	0.5054	1.1451	0.039*
C4	0.2977 (8)	0.6786 (5)	0.9324 (6)	0.0418 (12)
H4A	0.2870	0.6800	0.8258	0.050*
H4B	0.4254	0.6409	0.9801	0.050*
C5	−0.1232 (9)	0.6802 (5)	0.7472 (6)	0.0436 (12)
H5A	−0.2038	0.6300	0.6647	0.052*
H5B	−0.0093	0.7151	0.7159	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0684 (4)	0.0245 (3)	0.0521 (4)	−0.0120 (2)	0.0153 (3)	−0.0004 (2)
Br2	0.0617 (4)	0.0330 (3)	0.0511 (4)	0.0115 (2)	0.0074 (3)	0.0044 (2)
C1	0.047 (3)	0.018 (2)	0.035 (2)	−0.0032 (18)	0.019 (2)	−0.0069 (17)
C2	0.049 (3)	0.019 (2)	0.029 (2)	0.0046 (18)	0.014 (2)	−0.0026 (16)
C3	0.038 (2)	0.023 (2)	0.035 (2)	−0.0028 (17)	0.0068 (19)	−0.0061 (18)
C4	0.052 (3)	0.031 (3)	0.050 (3)	−0.010 (2)	0.026 (3)	−0.010 (2)
C5	0.063 (3)	0.034 (3)	0.037 (3)	0.008 (2)	0.017 (2)	0.002 (2)

Geometric parameters (Å, º)

Br1—C4	1.962 (5)	C3—C2^i	1.380 (6)
Br2—C5	1.956 (5)	C3—H3	0.93
C1—C3	1.389 (6)	C4—H4A	0.97
C1—C2	1.398 (7)	C4—H4B	0.97
C1—C4	1.508 (6)	C5—H5A	0.97
C2—C3^i	1.380 (6)	C5—H5B	0.97
C2—C5	1.495 (7)
C3—C1—C2	119.1 (4)	Br1—C4—H4A	109.4
C3—C1—C4	117.4 (4)	C1—C4—H4B	109.4
C2—C1—C4	123.4 (4)	Br1—C4—H4B	109.4
C3^i—C2—C1	118.4 (4)	H4A—C4—H4B	108.0
C3^i—C2—C5	119.4 (5)	C2—C5—Br2	110.4 (3)
C1—C2—C5	122.2 (4)	C2—C5—H5A	109.6
C2^i—C3—C1	122.5 (4)	Br2—C5—H5A	109.6
C2^i—C3—H3	118.7	C2—C5—H5B	109.6
C1—C3—H3	118.7	Br2—C5—H5B	109.6
C1—C4—Br1	111.3 (3)	H5A—C5—H5B	108.1
C1—C4—H4A	109.4
C3—C1—C2—C3^i	−0.7 (7)	C4—C1—C3—C2^i	−176.4 (4)
C4—C1—C2—C3^i	176.2 (4)	C3—C1—C4—Br1	−101.9 (4)
C3—C1—C2—C5	179.3 (4)	C2—C1—C4—Br1	81.1 (5)
C4—C1—C2—C5	−3.8 (7)	C3^i—C2—C5—Br2	78.0 (5)
C2—C1—C3—C2^i	0.7 (7)	C1—C2—C5—Br2	−101.9 (5)

Symmetry code: (i) −x, −y+1, −z+2.