1-(2,2-Dibromo­vin­yl)-3,5-dimeth­oxy­benzene

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

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

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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

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Computing details

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

Crystal data

C10H10Br2O2	Dx = 1.800 Mg m^−3
Mr = 321.98	Melting point: 345 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 4.129 (2) Å	Cell parameters from 1498 reflections
b = 11.192 (6) Å	θ = 2.4–22.5°
c = 25.732 (15) Å	µ = 6.80 mm^−1
β = 92.274 (10)°	T = 294 K
V = 1188.2 (11) Å^3	Block, colorless
Z = 4	0.26 × 0.24 × 0.12 mm
F(000) = 624

Data collection

CCD area detector diffractometer	2086 independent reflections
Radiation source: fine-focus sealed tube	1422 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
phi and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→4
Tmin = 0.186, Tmax = 0.442	k = −13→12
5582 measured reflections	l = −30→23

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.066	H-atom parameters constrained
wR(F^2) = 0.194	w = 1/[σ^2(Fo^2) + (0.0831P)^2 + 5.9795P] where P = (Fo^2 + 2Fc^2)/3
S = 1.18	(Δ/σ)max < 0.001
2086 reflections	Δρmax = 1.00 e Å^−3
130 parameters	Δρmin = −0.82 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.6528 (3)	0.66784 (10)	0.20443 (5)	0.0506 (5)
Br2	0.3449 (3)	0.40741 (10)	0.22553 (4)	0.0452 (5)
O1	0.051 (2)	0.3094 (7)	−0.0342 (3)	0.051 (2)
O2	0.497 (2)	0.0420 (6)	0.1005 (3)	0.050 (2)
C1	0.512 (2)	0.5157 (9)	0.1750 (4)	0.033 (2)
C2	0.543 (3)	0.4929 (10)	0.1230 (4)	0.039 (3)
H2	0.6288	0.5540	0.1033	0.047*
C3	0.451 (3)	0.3786 (9)	0.0943 (4)	0.031 (2)
C4	0.301 (3)	0.3912 (9)	0.0442 (4)	0.038 (3)
H4	0.2620	0.4670	0.0304	0.046*
C5	0.208 (3)	0.2878 (9)	0.0148 (4)	0.033 (2)
C6	0.273 (3)	0.1721 (10)	0.0350 (4)	0.039 (3)
H6	0.2106	0.1046	0.0160	0.046*
C7	0.434 (3)	0.1605 (9)	0.0842 (4)	0.040 (3)
C8	0.527 (3)	0.2618 (10)	0.1142 (4)	0.036 (3)
H8	0.6367	0.2528	0.1463	0.043*
C9	−0.067 (3)	0.2056 (11)	−0.0643 (5)	0.052 (3)
H9A	0.1122	0.1548	−0.0720	0.078*
H9B	−0.1718	0.2323	−0.0962	0.078*
H9C	−0.2190	0.1618	−0.0444	0.078*
C10	0.663 (3)	0.0253 (11)	0.1518 (4)	0.055 (3)
H10A	0.8838	0.0518	0.1503	0.082*
H10B	0.6598	−0.0578	0.1611	0.082*
H10C	0.5543	0.0709	0.1775	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0625 (9)	0.0327 (7)	0.0561 (9)	−0.0036 (6)	−0.0049 (6)	−0.0132 (5)
Br2	0.0551 (8)	0.0426 (7)	0.0387 (7)	−0.0003 (6)	0.0122 (5)	0.0025 (5)
O1	0.079 (6)	0.038 (4)	0.033 (4)	−0.001 (4)	−0.008 (4)	−0.004 (3)
O2	0.073 (6)	0.027 (4)	0.049 (5)	0.010 (4)	−0.013 (4)	0.000 (4)
C1	0.035 (6)	0.032 (6)	0.032 (6)	0.000 (5)	−0.009 (5)	0.000 (4)
C2	0.045 (7)	0.033 (6)	0.038 (6)	−0.008 (5)	−0.009 (5)	0.005 (5)
C3	0.039 (6)	0.031 (5)	0.025 (5)	−0.006 (5)	0.009 (4)	−0.006 (4)
C4	0.050 (7)	0.026 (6)	0.039 (6)	0.002 (5)	0.006 (5)	0.001 (5)
C5	0.040 (6)	0.031 (6)	0.029 (6)	−0.001 (5)	0.005 (5)	0.004 (4)
C6	0.051 (7)	0.038 (6)	0.027 (6)	0.004 (5)	0.011 (5)	0.000 (5)
C7	0.055 (7)	0.026 (5)	0.038 (6)	−0.001 (5)	0.011 (5)	0.002 (5)
C8	0.039 (6)	0.040 (6)	0.029 (6)	0.003 (5)	0.009 (5)	0.007 (5)
C9	0.066 (9)	0.054 (8)	0.034 (6)	−0.010 (7)	−0.015 (6)	−0.011 (6)
C10	0.075 (9)	0.049 (7)	0.039 (7)	0.018 (7)	−0.007 (6)	0.003 (6)

Geometric parameters (Å, º)

Br1—C1	1.944 (10)	C4—H4	0.9300
Br2—C1	1.925 (11)	C5—C6	1.417 (15)
O1—C5	1.415 (13)	C6—C7	1.413 (15)
O1—C9	1.469 (13)	C6—H6	0.9300
O2—C7	1.412 (13)	C7—C8	1.416 (15)
O2—C10	1.475 (13)	C8—H8	0.9300
C1—C2	1.371 (14)	C9—H9A	0.9600
C2—C3	1.517 (14)	C9—H9B	0.9600
C2—H2	0.9300	C9—H9C	0.9600
C3—C4	1.418 (15)	C10—H10A	0.9600
C3—C8	1.434 (14)	C10—H10B	0.9600
C4—C5	1.425 (15)	C10—H10C	0.9600
C5—O1—C9	117.8 (8)	C5—C6—H6	120.4
C7—O2—C10	117.3 (9)	O2—C7—C6	115.3 (9)
C2—C1—Br2	126.3 (8)	O2—C7—C8	123.2 (10)
C2—C1—Br1	120.3 (8)	C6—C7—C8	121.5 (10)
Br2—C1—Br1	113.4 (5)	C7—C8—C3	119.0 (10)
C1—C2—C3	126.9 (10)	C7—C8—H8	120.5
C1—C2—H2	116.6	C3—C8—H8	120.5
C3—C2—H2	116.6	O1—C9—H9A	109.5
C4—C3—C8	119.8 (9)	O1—C9—H9B	109.5
C4—C3—C2	116.8 (9)	H9A—C9—H9B	109.5
C8—C3—C2	123.2 (9)	O1—C9—H9C	109.5
C3—C4—C5	120.0 (9)	H9A—C9—H9C	109.5
C3—C4—H4	120.0	H9B—C9—H9C	109.5
C5—C4—H4	120.0	O2—C10—H10A	109.5
O1—C5—C6	123.7 (9)	O2—C10—H10B	109.5
O1—C5—C4	115.9 (9)	H10A—C10—H10B	109.5
C6—C5—C4	120.3 (9)	O2—C10—H10C	109.5
C7—C6—C5	119.2 (10)	H10A—C10—H10C	109.5
C7—C6—H6	120.4	H10B—C10—H10C	109.5
Br2—C1—C2—C3	0.4 (17)	O1—C5—C6—C7	179.4 (10)
Br1—C1—C2—C3	178.7 (8)	C4—C5—C6—C7	−0.7 (16)
C1—C2—C3—C4	139.6 (11)	C10—O2—C7—C6	−179.7 (10)
C1—C2—C3—C8	−44.3 (17)	C10—O2—C7—C8	1.2 (16)
C8—C3—C4—C5	3.7 (15)	C5—C6—C7—O2	−178.2 (9)
C2—C3—C4—C5	179.9 (10)	C5—C6—C7—C8	0.9 (16)
C9—O1—C5—C6	3.8 (16)	O2—C7—C8—C3	−179.8 (10)
C9—O1—C5—C4	−176.1 (10)	C6—C7—C8—C3	1.2 (16)
C3—C4—C5—O1	178.4 (9)	C4—C3—C8—C7	−3.4 (15)
C3—C4—C5—C6	−1.6 (16)	C2—C3—C8—C7	−179.5 (10)