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The configuration in the solid state structure of the title compound, C11H11BrO2, about the C=C double bond is E. In the crystal structure, symmetry-related mol­ecules are linked by O—H...O hydrogen bonds, forming centrosymmetric carboxylic acid dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807018843/ez2071sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807018843/ez2071Isup2.hkl
Contains datablock I

CCDC reference: 647191

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.026
  • wR factor = 0.067
  • Data-to-parameter ratio = 18.6

checkCIF/PLATON results

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Alert level C PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.12 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 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 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-Plus (Bruker, 2000); data reduction: XPREP (Bruker, 2000); program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTO (Meetsma, 2007) and PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

3-(4-Bromophenyl)-2-ethylacrylic acid top
Crystal data top
C11H11BrO2F(000) = 512
Mr = 255.11The final unit cell was obtained from the xyz centroids of 4668 reflections after integration using the SAINTPLUS software package (Bruker, 2000).
Reduced cell calculations did not indicate any higher metric lattice symmetry and examination of the finalatomic coordinates of the structure did not yield extra symmetry elements (Spek, 1988; Le Page 1987, 1988)
Monoclinic, P21/cDx = 1.695 Mg m3
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 11.9803 (9) ÅCell parameters from 4668 reflections
b = 5.0008 (4) Åθ = 2.5–29.7°
c = 16.986 (1) ŵ = 4.10 mm1
β = 101.880 (1)°T = 100 K
V = 995.85 (12) Å3Block, colourless
Z = 40.49 × 0.39 × 0.21 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2461 independent reflections
Radiation source: fine focus sealed Siemens Mo tube2168 reflections with I > 2σ(I)
Parallel mounted graphite monochromatorRint = 0.026
Detector resolution: 66.06 pixels mm-1θmax = 28.3°, θmin = 2.5°
φ and ω scansh = 1515
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
k = 66
Tmin = 0.164, Tmax = 0.423l = 2122
8570 measured reflections
Refinement top
Refinement on F2Primary atom site location: heavy-atom method
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: difference Fourier map
wR(F2) = 0.067H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.035P)2 + 0.5488P]
where P = (Fo2 + 2Fc2)/3
2461 reflections(Δ/σ)max < 0.001
132 parametersΔρmax = 0.73 e Å3
0 restraintsΔρmin = 0.47 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Br0.10293 (1)0.00456 (3)0.11662 (1)0.0179 (1)
O10.48650 (11)1.2836 (3)0.40981 (8)0.0180 (4)
O20.39590 (10)1.3078 (2)0.51247 (7)0.0177 (3)
C10.17990 (15)0.5620 (3)0.29802 (11)0.0152 (4)
C20.12616 (14)0.3632 (3)0.24646 (10)0.0153 (4)
C30.17875 (14)0.2639 (3)0.18739 (10)0.0153 (4)
C40.28467 (15)0.3581 (3)0.17836 (11)0.0166 (5)
C50.33695 (15)0.5577 (4)0.22982 (11)0.0171 (5)
C60.28693 (13)0.6633 (3)0.29121 (10)0.0136 (4)
C70.34837 (13)0.8779 (3)0.34163 (10)0.0142 (5)
C80.33502 (14)0.9728 (3)0.41337 (11)0.0137 (4)
C90.25341 (14)0.8740 (3)0.46371 (10)0.0151 (5)
C100.14192 (15)1.0335 (3)0.44993 (12)0.0188 (5)
C110.40807 (13)1.2020 (3)0.44961 (10)0.0136 (4)
H10.143600.630370.338520.0183*
H20.053880.296370.251820.0183*
H40.320420.287470.137880.0199*
H50.408680.625130.223410.0205*
H70.406550.962840.320230.0170*
H90.290930.885270.521260.0181*
H9'0.235620.683620.450880.0181*
H100.158851.222200.462640.0281*
H10'0.092950.963480.484790.0281*
H10"0.102621.016800.393540.0281*
H110.517 (3)1.414 (7)0.4302 (19)0.053 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.0228 (1)0.0143 (1)0.0161 (1)0.0014 (1)0.0026 (1)0.0027 (1)
O10.0158 (6)0.0185 (6)0.0209 (7)0.0061 (5)0.0064 (5)0.0031 (5)
O20.0177 (6)0.0169 (6)0.0191 (6)0.0045 (5)0.0050 (5)0.0026 (5)
C10.0146 (8)0.0158 (7)0.0157 (8)0.0014 (6)0.0042 (7)0.0003 (7)
C20.0144 (7)0.0149 (8)0.0166 (8)0.0005 (6)0.0033 (7)0.0021 (6)
C30.0185 (8)0.0115 (7)0.0147 (8)0.0000 (6)0.0010 (7)0.0005 (6)
C40.0189 (8)0.0157 (8)0.0164 (8)0.0026 (6)0.0066 (7)0.0007 (6)
C50.0154 (8)0.0176 (7)0.0195 (9)0.0006 (6)0.0063 (7)0.0014 (7)
C60.0134 (7)0.0125 (7)0.0148 (8)0.0003 (6)0.0029 (6)0.0003 (6)
C70.0094 (7)0.0139 (8)0.0191 (9)0.0007 (6)0.0028 (6)0.0024 (6)
C80.0100 (7)0.0112 (7)0.0191 (9)0.0006 (5)0.0011 (7)0.0017 (6)
C90.0154 (8)0.0143 (8)0.0155 (8)0.0016 (6)0.0029 (7)0.0002 (6)
C100.0154 (8)0.0178 (8)0.0253 (10)0.0008 (6)0.0094 (8)0.0019 (7)
C110.0102 (7)0.0126 (7)0.0176 (8)0.0016 (6)0.0018 (6)0.0031 (6)
Geometric parameters (Å, º) top
Br—C31.9034 (16)C8—C91.508 (2)
O1—C111.330 (2)C9—C101.532 (2)
O2—C111.227 (2)C1—H10.9500
O1—H110.79 (4)C2—H20.9500
C1—C21.392 (2)C4—H40.9500
C1—C61.405 (2)C5—H50.9500
C2—C31.382 (2)C7—H70.9500
C3—C41.391 (2)C9—H90.9900
C4—C51.388 (3)C9—H9'0.9900
C5—C61.408 (2)C10—H100.9800
C6—C71.472 (2)C10—H10'0.9800
C7—C81.348 (2)C10—H10"0.9800
C8—C111.496 (2)
Br···C1i3.7246 (18)C2···H2xi3.0600
Br···C6i3.7042 (17)C4···H9iii2.9800
Br···C10ii3.7221 (18)C6···H9'2.9000
Br···H10iii3.1600C8···H12.9300
Br···H10'iv3.1900C9···H12.5700
O1···C6v3.376 (2)C10···H12.7700
O1···O2vi2.6716 (18)C11···H103.0400
O2···C11vi3.3641 (19)C11···H11vi2.81 (3)
O2···C9v3.3219 (19)H1···C82.9300
O2···O1vi2.6715 (18)H1···C92.5700
O2···C103.307 (2)H1···C102.7700
O1···H5vii2.9100H1···H9'2.0200
O1···H72.2800H1···H10"2.2400
O1···H9viii2.8100H2···C1xii2.9900
O2···H102.8200H2···C2xii3.0600
O2···H92.4800H4···O2iii2.5200
O2···H9'v2.7400H4···H9iii2.5400
O2···H11vi1.89 (3)H5···H72.3600
O2···H4ix2.5200H5···O1xiii2.9100
C1···Brv3.7246 (18)H7···O12.2800
C1···C93.180 (2)H7···H52.3600
C1···C103.593 (2)H9···O22.4800
C3···C6i3.587 (2)H9···O1viii2.8100
C3···C7i3.539 (2)H9···C4ix2.9800
C6···Brv3.7042 (17)H9···H4ix2.5400
C6···O1i3.376 (2)H9'···O2i2.7400
C6···C3v3.587 (2)H9'···C12.6200
C7···C3v3.539 (2)H9'···C62.9000
C8···C11viii3.564 (2)H9'···H12.0200
C9···C13.180 (2)H9'···H10i2.5100
C9···O2i3.3219 (19)H10···O22.8200
C10···C13.593 (2)H10···C113.0400
C10···O23.307 (2)H10···H9'v2.5100
C10···Brx3.7221 (18)H10···Brix3.1600
C11···C11viii3.211 (2)H10'···H10'xiv2.4200
C11···O2vi3.3641 (19)H10'···Brxv3.1900
C11···C8viii3.564 (2)H10"···C13.0500
C1···H10"3.0500H10"···H12.2400
C1···H2xi2.9900H11···O2vi1.89 (3)
C1···H9'2.6200H11···C11vi2.81 (3)
C11—O1—H11110 (2)C6—C1—H1119.00
C2—C1—C6121.15 (16)C1—C2—H2120.00
C1—C2—C3119.50 (16)C3—C2—H2120.00
Br—C3—C2118.83 (12)C3—C4—H4121.00
C2—C3—C4121.38 (15)C5—C4—H4121.00
Br—C3—C4119.78 (12)C4—C5—H5119.00
C3—C4—C5118.52 (16)C6—C5—H5119.00
C4—C5—C6122.03 (17)C6—C7—H7115.00
C1—C6—C5117.41 (15)C8—C7—H7115.00
C5—C6—C7117.79 (15)C8—C9—H9109.00
C1—C6—C7124.77 (15)C8—C9—H9'109.00
C6—C7—C8130.13 (15)C10—C9—H9109.00
C7—C8—C11118.28 (15)C10—C9—H9'109.00
C9—C8—C11114.23 (14)H9—C9—H9'108.00
C7—C8—C9127.49 (15)C9—C10—H10109.00
C8—C9—C10112.92 (13)C9—C10—H10'109.00
O1—C11—C8116.16 (14)C9—C10—H10"109.00
O2—C11—C8121.63 (15)H10—C10—H10'109.00
O1—C11—O2122.22 (15)H10—C10—H10"109.00
C2—C1—H1119.00H10'—C10—H10"109.00
C6—C1—C2—C30.2 (2)C1—C6—C7—C818.6 (3)
C2—C1—C6—C50.6 (2)C5—C6—C7—C8163.67 (18)
C2—C1—C6—C7178.30 (15)C6—C7—C8—C92.3 (3)
C1—C2—C3—Br179.19 (12)C6—C7—C8—C11177.88 (15)
C1—C2—C3—C40.1 (2)C7—C8—C9—C1095.5 (2)
Br—C3—C4—C5178.74 (13)C11—C8—C9—C1084.67 (18)
C2—C3—C4—C50.6 (2)C7—C8—C11—O14.2 (2)
C3—C4—C5—C61.1 (3)C7—C8—C11—O2175.82 (15)
C4—C5—C6—C11.1 (3)C9—C8—C11—O1175.65 (14)
C4—C5—C6—C7178.93 (16)C9—C8—C11—O24.4 (2)
Symmetry codes: (i) x, y1, z; (ii) x, y3/2, z+1/2; (iii) x, y+3/2, z1/2; (iv) x, y+1/2, z1/2; (v) x, y+1, z; (vi) x+1, y+3, z+1; (vii) x+1, y+1/2, z+1/2; (viii) x+1, y+2, z+1; (ix) x, y+3/2, z+1/2; (x) x, y+3/2, z+1/2; (xi) x, y+1/2, z+1/2; (xii) x, y1/2, z+1/2; (xiii) x+1, y1/2, z+1/2; (xiv) x, y+2, z+1; (xv) x, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H11···O2vi0.79 (4)1.89 (3)2.6716 (18)172 (3)
C4—H4···O2iii0.952.523.457 (2)167
C7—H7···O10.952.282.722 (2)107
Symmetry codes: (iii) x, y+3/2, z1/2; (vi) x+1, y+3, z+1.
 

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