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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806042334/ci2194sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806042334/ci2194Isup2.hkl
Contains datablock I

CCDC reference: 627466

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

Computing details top

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 top
Crystal data top
C10H10Br4F(000) = 420
Mr = 449.82Dx = 2.417 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1394 reflections
a = 6.9695 (14) Åθ = 3.0–27.1°
b = 9.880 (2) ŵ = 12.98 mm1
c = 9.2352 (19) ÅT = 298 K
β = 103.638 (4)°Block, colourless
V = 618.0 (2) Å30.20 × 0.20 × 0.20 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
1343 independent reflections
Radiation source: fine-focus sealed tube1067 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
φ and ω scansθmax = 27.0°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 88
Tmin = 0.181, Tmax = 0.181k = 1112
3526 measured reflectionsl = 611
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.045P)2 + 0.7024P]
where P = (Fo2 + 2Fc2)/3
1343 reflections(Δ/σ)max = 0.001
64 parametersΔρmax = 0.57 e Å3
0 restraintsΔρmin = 0.61 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Br10.27950 (9)0.86420 (5)1.00357 (6)0.0482 (2)
Br20.27607 (9)0.83080 (5)0.79953 (6)0.0496 (2)
C10.1369 (7)0.5903 (4)0.9656 (5)0.0316 (10)
C20.0561 (7)0.5880 (4)0.8778 (5)0.0314 (10)
C30.1882 (7)0.5028 (4)1.0863 (5)0.0321 (10)
H30.31630.50541.14510.039*
C40.2977 (8)0.6786 (5)0.9324 (6)0.0418 (12)
H4A0.28700.68000.82580.050*
H4B0.42540.64090.98010.050*
C50.1232 (9)0.6802 (5)0.7472 (6)0.0436 (12)
H5A0.20380.63000.66470.052*
H5B0.00930.71510.71590.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0684 (4)0.0245 (3)0.0521 (4)0.0120 (2)0.0153 (3)0.0004 (2)
Br20.0617 (4)0.0330 (3)0.0511 (4)0.0115 (2)0.0074 (3)0.0044 (2)
C10.047 (3)0.018 (2)0.035 (2)0.0032 (18)0.019 (2)0.0069 (17)
C20.049 (3)0.019 (2)0.029 (2)0.0046 (18)0.014 (2)0.0026 (16)
C30.038 (2)0.023 (2)0.035 (2)0.0028 (17)0.0068 (19)0.0061 (18)
C40.052 (3)0.031 (3)0.050 (3)0.010 (2)0.026 (3)0.010 (2)
C50.063 (3)0.034 (3)0.037 (3)0.008 (2)0.017 (2)0.002 (2)
Geometric parameters (Å, º) top
Br1—C41.962 (5)C3—C2i1.380 (6)
Br2—C51.956 (5)C3—H30.93
C1—C31.389 (6)C4—H4A0.97
C1—C21.398 (7)C4—H4B0.97
C1—C41.508 (6)C5—H5A0.97
C2—C3i1.380 (6)C5—H5B0.97
C2—C51.495 (7)
C3—C1—C2119.1 (4)Br1—C4—H4A109.4
C3—C1—C4117.4 (4)C1—C4—H4B109.4
C2—C1—C4123.4 (4)Br1—C4—H4B109.4
C3i—C2—C1118.4 (4)H4A—C4—H4B108.0
C3i—C2—C5119.4 (5)C2—C5—Br2110.4 (3)
C1—C2—C5122.2 (4)C2—C5—H5A109.6
C2i—C3—C1122.5 (4)Br2—C5—H5A109.6
C2i—C3—H3118.7C2—C5—H5B109.6
C1—C3—H3118.7Br2—C5—H5B109.6
C1—C4—Br1111.3 (3)H5A—C5—H5B108.1
C1—C4—H4A109.4
C3—C1—C2—C3i0.7 (7)C4—C1—C3—C2i176.4 (4)
C4—C1—C2—C3i176.2 (4)C3—C1—C4—Br1101.9 (4)
C3—C1—C2—C5179.3 (4)C2—C1—C4—Br181.1 (5)
C4—C1—C2—C53.8 (7)C3i—C2—C5—Br278.0 (5)
C2—C1—C3—C2i0.7 (7)C1—C2—C5—Br2101.9 (5)
Symmetry code: (i) x, y+1, z+2.
 

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