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In the crystal structure of the title mol­ecule, C8H8Br2, there is a single C—H...π(arene) inter­action.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048422/lh2233sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048422/lh2233Isup2.hkl
Contains datablock I

CCDC reference: 630093

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.050
  • wR factor = 0.135
  • Data-to-parameter ratio = 21.2

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.151 0.406 Tmin and Tmax expected: 0.129 0.406 RR = 1.172 Please check that your absorption correction is appropriate. PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.14 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C7 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 3 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

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

1,1-Dibromo-m-xylene top
Crystal data top
C8H8Br2F(000) = 504
Mr = 263.96Dx = 1.963 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1879 reflections
a = 13.084 (2) Åθ = 2.7–25.2°
b = 4.5374 (8) ŵ = 9.00 mm1
c = 15.075 (3) ÅT = 298 K
β = 93.846 (3)°Plate, colorless
V = 893.0 (3) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
1933 independent reflections
Radiation source: fine-focus sealed tube1221 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
φ and ω scansθmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1616
Tmin = 0.151, Tmax = 0.406k = 55
6118 measured reflectionsl = 1519
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0726P)2]
where P = (Fo2 + 2Fc2)/3
1933 reflections(Δ/σ)max = 0.001
91 parametersΔρmax = 0.75 e Å3
0 restraintsΔρmin = 0.52 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
Br11.14084 (4)0.13612 (12)0.54062 (4)0.0657 (3)
Br20.78109 (4)0.11695 (13)0.88989 (4)0.0714 (3)
C11.0528 (4)0.2013 (10)0.7084 (3)0.0485 (12)
C20.9747 (3)0.0101 (10)0.7284 (3)0.0472 (12)
H20.92240.02930.68520.057*
C30.9724 (4)0.1217 (9)0.8098 (4)0.0495 (12)
C41.0508 (4)0.0605 (12)0.8732 (4)0.0632 (14)
H41.05110.14880.92890.076*
C51.1285 (4)0.1305 (12)0.8546 (4)0.0684 (16)
H51.18060.17260.89770.082*
C61.1286 (4)0.2572 (13)0.7726 (4)0.0623 (14)
H61.18140.38460.76020.075*
C71.0501 (5)0.3407 (12)0.6194 (4)0.0758 (18)
H7A1.07120.54510.62570.091*
H7B0.98050.33720.59290.091*
C80.8883 (4)0.3254 (12)0.8302 (5)0.0717 (17)
H8A0.91570.48340.86810.086*
H8B0.85910.41240.77540.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0676 (4)0.0718 (4)0.0609 (4)0.0019 (3)0.0273 (3)0.0036 (3)
Br20.0634 (4)0.0832 (5)0.0705 (5)0.0103 (3)0.0271 (3)0.0021 (3)
C10.058 (3)0.038 (2)0.053 (3)0.010 (2)0.022 (2)0.002 (2)
C20.046 (2)0.044 (3)0.052 (3)0.009 (2)0.010 (2)0.007 (3)
C30.057 (3)0.041 (3)0.053 (3)0.005 (2)0.018 (2)0.003 (2)
C40.071 (3)0.066 (3)0.055 (4)0.016 (3)0.014 (3)0.006 (3)
C50.055 (3)0.089 (4)0.061 (4)0.002 (3)0.001 (3)0.012 (3)
C60.051 (3)0.055 (3)0.083 (4)0.006 (2)0.020 (3)0.010 (3)
C70.095 (4)0.057 (3)0.080 (5)0.023 (3)0.039 (4)0.015 (3)
C80.082 (4)0.054 (3)0.083 (5)0.005 (3)0.037 (3)0.009 (3)
Geometric parameters (Å, º) top
Br1—C71.967 (5)C4—C51.379 (7)
Br2—C81.961 (5)C4—H40.9300
C1—C61.362 (7)C5—C61.363 (8)
C1—C21.389 (6)C5—H50.9300
C1—C71.482 (7)C6—H60.9300
C2—C31.367 (7)C7—H7A0.9700
C2—H20.9300C7—H7B0.9700
C3—C41.383 (7)C8—H8A0.9700
C3—C81.485 (7)C8—H8B0.9700
C6—C1—C2118.3 (5)C1—C6—C5121.4 (5)
C6—C1—C7122.4 (5)C1—C6—H6119.3
C2—C1—C7119.4 (5)C5—C6—H6119.3
C3—C2—C1121.9 (5)C1—C7—Br1111.5 (3)
C3—C2—H2119.0C1—C7—H7A109.3
C1—C2—H2119.0Br1—C7—H7A109.3
C2—C3—C4118.2 (5)C1—C7—H7B109.3
C2—C3—C8121.3 (5)Br1—C7—H7B109.3
C4—C3—C8120.5 (5)H7A—C7—H7B108.0
C5—C4—C3120.5 (5)C3—C8—Br2111.0 (3)
C5—C4—H4119.7C3—C8—H8A109.4
C3—C4—H4119.7Br2—C8—H8A109.4
C6—C5—C4119.7 (5)C3—C8—H8B109.4
C6—C5—H5120.2Br2—C8—H8B109.4
C4—C5—H5120.2H8A—C8—H8B108.0
C6—C1—C2—C30.2 (7)C2—C1—C6—C50.1 (8)
C7—C1—C2—C3179.1 (4)C7—C1—C6—C5178.8 (5)
C1—C2—C3—C40.0 (6)C4—C5—C6—C10.5 (8)
C1—C2—C3—C8180.0 (4)C6—C1—C7—Br181.3 (6)
C2—C3—C4—C50.5 (7)C2—C1—C7—Br199.9 (5)
C8—C3—C4—C5179.5 (5)C2—C3—C8—Br295.4 (5)
C3—C4—C5—C60.7 (8)C4—C3—C8—Br284.6 (5)
 

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