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The title compound, C12H22Br2, displays crystallographic inversion symmetry. Bond lengths C=C = 1.352 (4) Å and Csp2—Csp3 = 1.574 (3) Å are inter­preted as symptoms of steric overcrowding. Mol­ecules are linked into chains parallel to [101] by Br...Br inter­actions of 3.4275 (9) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806009627/fl2012sup1.cif
Contains datablocks 2, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806009627/fl20122sup2.hkl
Contains datablock 2

CCDC reference: 605238

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.027
  • wR factor = 0.068
  • Data-to-parameter ratio = 21.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.63
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT412_ALERT_2_C Short Intra XH3 .. XHn H3A .. H6B .. 1.89 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Br .. Br .. 3.43 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 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 2 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

Computing details top

Data collection: DIF4 (Stoe & Cie, 1992); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1992); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

(E)-3,4-bis(bromomethyl)-2,2,5,5-tetramethylhex-3-ene top
Crystal data top
C12H22Br2F(000) = 656
Mr = 326.12Dx = 1.671 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 15.658 (4) ÅCell parameters from 60 reflections
b = 7.3521 (12) Åθ = 10–11.5°
c = 11.284 (2) ŵ = 6.22 mm1
β = 93.53 (2)°T = 173 K
V = 1296.6 (5) Å3Block, colourless
Z = 40.5 × 0.4 × 0.4 mm
Data collection top
Stoe STADI4
diffractometer
1341 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
Graphite monochromatorθmax = 27.5°, θmin = 3.1°
ω/θ scansh = 2020
Absorption correction: ψ scan
(XEMP; Siemens, 1994)
k = 94
Tmin = 0.035, Tmax = 0.083l = 014
2458 measured reflections3 standard reflections every 60 min
1487 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027H-atom parameters constrained
wR(F2) = 0.068 w = 1/[σ2(Fo2) + (0.0302P)2 + 1.7902P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
1487 reflectionsΔρmax = 0.60 e Å3
70 parametersΔρmin = 0.57 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0023 (4)
Special details top

Experimental. MS (70 eV): m/z (%) = 328 (3), 326 (6), 324 (3) [M+], 247 (5), 245 (5), 83 (100), 58 (78)

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
Br0.435600 (14)0.11695 (4)0.62158 (2)0.03111 (13)
C10.28891 (12)0.2506 (3)0.47719 (17)0.0142 (4)
C20.32972 (14)0.4144 (3)0.41075 (19)0.0173 (4)
C30.27146 (15)0.4888 (3)0.3070 (2)0.0246 (5)
H3A0.22520.56060.33840.030*
H3B0.24700.38720.26000.030*
H3C0.30510.56600.25660.030*
C40.35479 (16)0.5664 (3)0.4995 (2)0.0255 (5)
H4A0.39480.51840.56200.031*
H4B0.30340.61210.53520.031*
H4C0.38210.66590.45810.031*
C50.41272 (16)0.3583 (3)0.3529 (2)0.0263 (5)
H5A0.45360.30860.41380.032*
H5B0.43780.46510.31630.032*
H5C0.39940.26580.29210.032*
C60.34563 (14)0.0873 (3)0.49072 (19)0.0179 (4)
H6A0.37320.06580.41540.022 (7)*
H6B0.31040.02070.50680.027 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.01868 (16)0.04656 (19)0.02728 (17)0.00689 (9)0.00526 (10)0.00523 (10)
C10.0149 (9)0.0148 (9)0.0125 (9)0.0003 (7)0.0011 (7)0.0007 (7)
C20.0151 (10)0.0186 (10)0.0188 (10)0.0017 (8)0.0057 (8)0.0005 (8)
C30.0281 (11)0.0265 (11)0.0197 (11)0.0022 (9)0.0043 (9)0.0079 (9)
C40.0264 (12)0.0223 (11)0.0282 (12)0.0073 (9)0.0052 (10)0.0052 (9)
C50.0205 (11)0.0324 (12)0.0269 (12)0.0007 (9)0.0091 (10)0.0038 (10)
C60.0151 (10)0.0197 (10)0.0188 (10)0.0020 (8)0.0005 (8)0.0014 (8)
Geometric parameters (Å, º) top
Br—C61.989 (2)C3—H3C0.9800
C1—C1i1.352 (4)C4—H4A0.9800
C1—C61.495 (3)C4—H4B0.9800
C1—C21.574 (3)C4—H4C0.9800
C2—C41.536 (3)C5—H5A0.9800
C2—C31.540 (3)C5—H5B0.9800
C2—C51.546 (3)C5—H5C0.9800
C3—H3A0.9800C6—H6A0.9900
C3—H3B0.9800C6—H6B0.9900
C1i—C1—C6120.0 (2)C2—C4—H4B109.5
C1i—C1—C2126.0 (2)H4A—C4—H4B109.5
C6—C1—C2113.99 (17)C2—C4—H4C109.5
C4—C2—C3110.66 (19)H4A—C4—H4C109.5
C4—C2—C5106.36 (18)H4B—C4—H4C109.5
C3—C2—C5104.35 (18)C2—C5—H5A109.5
C4—C2—C1109.93 (18)C2—C5—H5B109.5
C3—C2—C1113.28 (18)H5A—C5—H5B109.5
C5—C2—C1111.94 (17)C2—C5—H5C109.5
C1—C6—Br112.14 (14)H5A—C5—H5C109.5
C2—C3—H3A109.5H5B—C5—H5C109.5
C2—C3—H3B109.5C1—C6—H6A109.2
H3A—C3—H3B109.5Br—C6—H6A109.2
C2—C3—H3C109.5C1—C6—H6B109.2
H3A—C3—H3C109.5Br—C6—H6B109.2
H3B—C3—H3C109.5H6A—C6—H6B107.9
C2—C4—H4A109.5
C1i—C1—C2—C471.3 (3)C6—C1—C2—C510.9 (3)
C6—C1—C2—C4107.1 (2)C1i—C1—C6—Br100.3 (3)
C1i—C1—C2—C353.1 (3)C2—C1—C6—Br78.20 (19)
C6—C1—C2—C3128.51 (19)C6—C1—C1i—C2i1.7 (4)
C1i—C1—C2—C5170.7 (3)
Symmetry code: (i) x+1/2, y+1/2, z+1.
 

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