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The title compound, C12H11BrO4, is an allylic bromide, which is an inter­esting precursor in organic synthesis. The skeleton of the mol­ecule is nearly planar, indicating delocalization. The crystal packing is governed by C—H...O hydrogen bonds, with the mol­ecules stacked along the [100] and [010] directions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602695X/rz2046sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680602695X/rz2046Isup2.hkl
Contains datablock I

CCDC reference: 618307

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.039
  • wR factor = 0.111
  • Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.32 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
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 2 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: SET4 in CAD-4 EXPRESS; data reduction: HELENA (Spek, 1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Methyl (Z)-2-(bromomethyl)-3-(3,4-methylenedioxyphenyl)prop-2-enoate top
Crystal data top
C12H11BrO4Z = 2
Mr = 299.12F(000) = 300
Triclinic, P1Dx = 1.699 Mg m3
a = 6.725 (3) ÅMo Kα radiation, λ = 0.71069 Å
b = 8.845 (2) ÅCell parameters from 25 reflections
c = 9.941 (1) Åθ = 4.1–13.4°
α = 91.41 (2)°µ = 3.52 mm1
β = 90.98 (2)°T = 293 K
γ = 98.490 (2)°Irregular block, colorless
V = 584.5 (3) Å30.50 × 0.47 × 0.43 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1691 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
Graphite monochromatorθmax = 25.5°, θmin = 2.1°
ω–2θ scansh = 88
Absorption correction: ψ scan
(North et al., 1968)
k = 1010
Tmin = 0.200, Tmax = 0.225l = 121
2567 measured reflections3 standard reflections every 200 reflections
2166 independent reflections intensity decay: 1%
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0595P)2 + 0.5446P]
where P = (Fo2 + 2Fc2)/3
2166 reflections(Δ/σ)max = 0.001
155 parametersΔρmax = 0.99 e Å3
0 restraintsΔρmin = 0.43 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.9019 (5)0.5965 (4)0.7446 (3)0.0384 (8)
C20.9570 (6)0.4637 (4)0.6828 (4)0.0448 (8)
H20.88460.41590.60900.054*
C31.1194 (5)0.4080 (4)0.7346 (4)0.0422 (8)
C41.2283 (5)0.4754 (4)0.8435 (4)0.0404 (8)
C51.1813 (6)0.6041 (4)0.9062 (4)0.0453 (9)
H51.25520.64900.98050.054*
C61.0179 (6)0.6650 (4)0.8540 (4)0.0423 (8)
H60.98460.75430.89320.051*
C70.7290 (5)0.6525 (4)0.6832 (4)0.0416 (8)
H70.69040.60610.60000.050*
C80.6144 (5)0.7564 (4)0.7214 (3)0.0391 (8)
C90.4523 (5)0.7800 (4)0.6233 (4)0.0410 (8)
C100.2000 (6)0.9269 (5)0.5684 (5)0.0570 (10)
H10A0.25480.95700.48290.086*
H10B0.13481.00730.60590.086*
H10C0.10410.83560.55640.086*
C111.3756 (7)0.2801 (6)0.7705 (5)0.0645 (12)
H11A1.49400.30140.71570.077*
H11B1.37430.18030.80890.077*
C120.6267 (6)0.8424 (4)0.8525 (4)0.0474 (9)
H12A0.67810.78160.92130.057*
H12B0.49280.85920.87770.057*
O11.1995 (5)0.2815 (3)0.6900 (3)0.0654 (8)
O21.3809 (4)0.3938 (3)0.8750 (3)0.0550 (7)
O30.3601 (4)0.8981 (3)0.6585 (3)0.0507 (7)
O40.4062 (4)0.7031 (4)0.5248 (3)0.0663 (9)
Br10.80250 (7)1.04154 (5)0.84506 (5)0.0651 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0405 (19)0.0337 (17)0.0403 (19)0.0041 (14)0.0058 (15)0.0000 (14)
C20.045 (2)0.0423 (19)0.046 (2)0.0071 (16)0.0101 (16)0.0077 (16)
C30.0416 (19)0.0375 (18)0.048 (2)0.0101 (15)0.0039 (16)0.0039 (15)
C40.0376 (18)0.0420 (18)0.0419 (19)0.0059 (15)0.0031 (15)0.0080 (15)
C50.049 (2)0.0441 (19)0.042 (2)0.0050 (16)0.0137 (17)0.0035 (16)
C60.047 (2)0.0363 (18)0.044 (2)0.0088 (15)0.0088 (16)0.0049 (15)
C70.0419 (19)0.0380 (18)0.043 (2)0.0034 (15)0.0088 (16)0.0058 (15)
C80.0410 (19)0.0358 (17)0.0400 (19)0.0050 (14)0.0056 (15)0.0005 (14)
C90.0380 (19)0.0385 (18)0.046 (2)0.0052 (15)0.0049 (16)0.0026 (15)
C100.055 (2)0.052 (2)0.067 (3)0.0204 (19)0.020 (2)0.002 (2)
C110.062 (3)0.076 (3)0.062 (3)0.036 (2)0.011 (2)0.009 (2)
C120.054 (2)0.050 (2)0.040 (2)0.0143 (17)0.0040 (17)0.0006 (16)
O10.0660 (19)0.0571 (17)0.077 (2)0.0297 (14)0.0217 (16)0.0233 (15)
O20.0526 (15)0.0570 (16)0.0589 (17)0.0220 (13)0.0156 (13)0.0009 (13)
O30.0543 (15)0.0469 (14)0.0537 (16)0.0200 (12)0.0152 (12)0.0075 (12)
O40.0606 (18)0.079 (2)0.0638 (18)0.0341 (15)0.0283 (15)0.0300 (16)
Br10.0721 (3)0.0483 (3)0.0737 (3)0.0110 (2)0.0246 (2)0.0182 (2)
Geometric parameters (Å, º) top
C1—C61.399 (5)C8—C91.492 (5)
C1—C21.413 (5)C9—O41.189 (4)
C1—C71.460 (5)C9—O31.333 (4)
C2—C31.362 (5)C10—O31.445 (4)
C2—H20.9300C10—H10A0.9600
C3—C41.370 (5)C10—H10B0.9600
C3—O11.378 (4)C10—H10C0.9600
C4—C51.365 (5)C11—O11.419 (5)
C4—O21.375 (4)C11—O21.424 (5)
C5—C61.392 (5)C11—H11A0.9700
C5—H50.9300C11—H11B0.9700
C6—H60.9300C12—Br11.975 (4)
C7—C81.335 (5)C12—H12A0.9700
C7—H70.9300C12—H12B0.9700
C8—C121.488 (5)
C6—C1—C2118.6 (3)O4—C9—O3122.6 (3)
C6—C1—C7125.9 (3)O4—C9—C8125.0 (3)
C2—C1—C7115.4 (3)O3—C9—C8112.5 (3)
C3—C2—C1117.9 (3)O3—C10—H10A109.5
C3—C2—H2121.1O3—C10—H10B109.5
C1—C2—H2121.1H10A—C10—H10B109.5
C2—C3—C4122.4 (3)O3—C10—H10C109.5
C2—C3—O1127.6 (3)H10A—C10—H10C109.5
C4—C3—O1110.0 (3)H10B—C10—H10C109.5
C5—C4—C3121.9 (3)O1—C11—O2108.6 (3)
C5—C4—O2128.3 (3)O1—C11—H11A110.0
C3—C4—O2109.8 (3)O2—C11—H11A110.0
C4—C5—C6117.0 (3)O1—C11—H11B110.0
C4—C5—H5121.5O2—C11—H11B110.0
C6—C5—H5121.5H11A—C11—H11B108.4
C5—C6—C1122.2 (3)C8—C12—Br1112.1 (3)
C5—C6—H6118.9C8—C12—H12A109.2
C1—C6—H6118.9Br1—C12—H12A109.2
C8—C7—C1133.5 (3)C8—C12—H12B109.2
C8—C7—H7113.2Br1—C12—H12B109.2
C1—C7—H7113.2H12A—C12—H12B107.9
C7—C8—C12126.6 (3)C3—O1—C11105.3 (3)
C7—C8—C9115.2 (3)C4—O2—C11105.4 (3)
C12—C8—C9118.1 (3)C9—O3—C10115.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O40.932.332.756 (5)108
C2—H2···O4i0.932.443.318 (5)158
C11—H11A···O4ii0.972.503.300 (6)140
C10—H10B···O1iii0.962.523.334 (5)143
C12—H12A···O2iv0.972.583.458 (5)150
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+1, z+1; (iii) x1, y+1, z; (iv) x+2, y+1, z+2.
 

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