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In the title compound, C10H10Br2O2, the angle between the dibromovinyl group and the benzene ring is 42.2 (2)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026262/bv2023sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026262/bv2023Isup2.hkl
Contains datablock I

CCDC reference: 620704

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.015 Å
  • R factor = 0.065
  • wR factor = 0.194
  • Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 15
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Molecular Structure Corporation & Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: CrystalStructure.

1-(2,2-dibromo-vinyl)-3,5-dimethoxy-benzene top
Crystal data top
C10H10Br2O2Dx = 1.800 Mg m3
Mr = 321.98Melting point: 345 K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 4.129 (2) ÅCell parameters from 1498 reflections
b = 11.192 (6) Åθ = 2.4–22.5°
c = 25.732 (15) ŵ = 6.80 mm1
β = 92.274 (10)°T = 294 K
V = 1188.2 (11) Å3Block, colorless
Z = 40.26 × 0.24 × 0.12 mm
F(000) = 624
Data collection top
CCD area detector
diffractometer
2086 independent reflections
Radiation source: fine-focus sealed tube1422 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
phi and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 44
Tmin = 0.186, Tmax = 0.442k = 1312
5582 measured reflectionsl = 3023
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)] = 0.066H-atom parameters constrained
wR(F2) = 0.194 w = 1/[σ2(Fo2) + (0.0831P)2 + 5.9795P]
where P = (Fo2 + 2Fc2)/3
S = 1.18(Δ/σ)max < 0.001
2086 reflectionsΔρmax = 1.00 e Å3
130 parametersΔρmin = 0.82 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.013 (2)
Special details top

Experimental. Spectroscopic analysis: 1H NMR (CDCl3, δ, p.p.m.): 7.41 (s, 1H), 6.68 (d, J = 2.1 Hz, 2H), 6.44 (brs, 1H), 3.79(s, 6H).

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
Br10.6528 (3)0.66784 (10)0.20443 (5)0.0506 (5)
Br20.3449 (3)0.40741 (10)0.22553 (4)0.0452 (5)
O10.051 (2)0.3094 (7)0.0342 (3)0.051 (2)
O20.497 (2)0.0420 (6)0.1005 (3)0.050 (2)
C10.512 (2)0.5157 (9)0.1750 (4)0.033 (2)
C20.543 (3)0.4929 (10)0.1230 (4)0.039 (3)
H20.62880.55400.10330.047*
C30.451 (3)0.3786 (9)0.0943 (4)0.031 (2)
C40.301 (3)0.3912 (9)0.0442 (4)0.038 (3)
H40.26200.46700.03040.046*
C50.208 (3)0.2878 (9)0.0148 (4)0.033 (2)
C60.273 (3)0.1721 (10)0.0350 (4)0.039 (3)
H60.21060.10460.01600.046*
C70.434 (3)0.1605 (9)0.0842 (4)0.040 (3)
C80.527 (3)0.2618 (10)0.1142 (4)0.036 (3)
H80.63670.25280.14630.043*
C90.067 (3)0.2056 (11)0.0643 (5)0.052 (3)
H9A0.11220.15480.07200.078*
H9B0.17180.23230.09620.078*
H9C0.21900.16180.04440.078*
C100.663 (3)0.0253 (11)0.1518 (4)0.055 (3)
H10A0.88380.05180.15030.082*
H10B0.65980.05780.16110.082*
H10C0.55430.07090.17750.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0625 (9)0.0327 (7)0.0561 (9)0.0036 (6)0.0049 (6)0.0132 (5)
Br20.0551 (8)0.0426 (7)0.0387 (7)0.0003 (6)0.0122 (5)0.0025 (5)
O10.079 (6)0.038 (4)0.033 (4)0.001 (4)0.008 (4)0.004 (3)
O20.073 (6)0.027 (4)0.049 (5)0.010 (4)0.013 (4)0.000 (4)
C10.035 (6)0.032 (6)0.032 (6)0.000 (5)0.009 (5)0.000 (4)
C20.045 (7)0.033 (6)0.038 (6)0.008 (5)0.009 (5)0.005 (5)
C30.039 (6)0.031 (5)0.025 (5)0.006 (5)0.009 (4)0.006 (4)
C40.050 (7)0.026 (6)0.039 (6)0.002 (5)0.006 (5)0.001 (5)
C50.040 (6)0.031 (6)0.029 (6)0.001 (5)0.005 (5)0.004 (4)
C60.051 (7)0.038 (6)0.027 (6)0.004 (5)0.011 (5)0.000 (5)
C70.055 (7)0.026 (5)0.038 (6)0.001 (5)0.011 (5)0.002 (5)
C80.039 (6)0.040 (6)0.029 (6)0.003 (5)0.009 (5)0.007 (5)
C90.066 (9)0.054 (8)0.034 (6)0.010 (7)0.015 (6)0.011 (6)
C100.075 (9)0.049 (7)0.039 (7)0.018 (7)0.007 (6)0.003 (6)
Geometric parameters (Å, º) top
Br1—C11.944 (10)C4—H40.9300
Br2—C11.925 (11)C5—C61.417 (15)
O1—C51.415 (13)C6—C71.413 (15)
O1—C91.469 (13)C6—H60.9300
O2—C71.412 (13)C7—C81.416 (15)
O2—C101.475 (13)C8—H80.9300
C1—C21.371 (14)C9—H9A0.9600
C2—C31.517 (14)C9—H9B0.9600
C2—H20.9300C9—H9C0.9600
C3—C41.418 (15)C10—H10A0.9600
C3—C81.434 (14)C10—H10B0.9600
C4—C51.425 (15)C10—H10C0.9600
C5—O1—C9117.8 (8)C5—C6—H6120.4
C7—O2—C10117.3 (9)O2—C7—C6115.3 (9)
C2—C1—Br2126.3 (8)O2—C7—C8123.2 (10)
C2—C1—Br1120.3 (8)C6—C7—C8121.5 (10)
Br2—C1—Br1113.4 (5)C7—C8—C3119.0 (10)
C1—C2—C3126.9 (10)C7—C8—H8120.5
C1—C2—H2116.6C3—C8—H8120.5
C3—C2—H2116.6O1—C9—H9A109.5
C4—C3—C8119.8 (9)O1—C9—H9B109.5
C4—C3—C2116.8 (9)H9A—C9—H9B109.5
C8—C3—C2123.2 (9)O1—C9—H9C109.5
C3—C4—C5120.0 (9)H9A—C9—H9C109.5
C3—C4—H4120.0H9B—C9—H9C109.5
C5—C4—H4120.0O2—C10—H10A109.5
O1—C5—C6123.7 (9)O2—C10—H10B109.5
O1—C5—C4115.9 (9)H10A—C10—H10B109.5
C6—C5—C4120.3 (9)O2—C10—H10C109.5
C7—C6—C5119.2 (10)H10A—C10—H10C109.5
C7—C6—H6120.4H10B—C10—H10C109.5
Br2—C1—C2—C30.4 (17)O1—C5—C6—C7179.4 (10)
Br1—C1—C2—C3178.7 (8)C4—C5—C6—C70.7 (16)
C1—C2—C3—C4139.6 (11)C10—O2—C7—C6179.7 (10)
C1—C2—C3—C844.3 (17)C10—O2—C7—C81.2 (16)
C8—C3—C4—C53.7 (15)C5—C6—C7—O2178.2 (9)
C2—C3—C4—C5179.9 (10)C5—C6—C7—C80.9 (16)
C9—O1—C5—C63.8 (16)O2—C7—C8—C3179.8 (10)
C9—O1—C5—C4176.1 (10)C6—C7—C8—C31.2 (16)
C3—C4—C5—O1178.4 (9)C4—C3—C8—C73.4 (15)
C3—C4—C5—C61.6 (16)C2—C3—C8—C7179.5 (10)
 

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