The configuration in the solid state structure of the title compound, C
11H
11BrO
2, 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
CCDC reference: 647191
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.026
- wR factor = 0.067
- Data-to-parameter ratio = 18.6
checkCIF/PLATON results
No syntax errors found
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
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
C11H11BrO2 | F(000) = 512 |
Mr = 255.11 | The 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/c | Dx = 1.695 Mg m−3 |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 11.9803 (9) Å | Cell parameters from 4668 reflections |
b = 5.0008 (4) Å | θ = 2.5–29.7° |
c = 16.986 (1) Å | µ = 4.10 mm−1 |
β = 101.880 (1)° | T = 100 K |
V = 995.85 (12) Å3 | Block, colourless |
Z = 4 | 0.49 × 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 tube | 2168 reflections with I > 2σ(I) |
Parallel mounted graphite monochromator | Rint = 0.026 |
Detector resolution: 66.06 pixels mm-1 | θmax = 28.3°, θmin = 2.5° |
φ and ω scans | h = −15→15 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | k = −6→6 |
Tmin = 0.164, Tmax = 0.423 | l = −21→22 |
8570 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: heavy-atom method |
Least-squares matrix: full | Secondary atom site location: structure-invariant direct methods |
R[F2 > 2σ(F2)] = 0.026 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.067 | H 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 parameters | Δρmax = 0.73 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Br | 0.10293 (1) | −0.00456 (3) | 0.11662 (1) | 0.0179 (1) | |
O1 | 0.48650 (11) | 1.2836 (3) | 0.40981 (8) | 0.0180 (4) | |
O2 | 0.39590 (10) | 1.3078 (2) | 0.51247 (7) | 0.0177 (3) | |
C1 | 0.17990 (15) | 0.5620 (3) | 0.29802 (11) | 0.0152 (4) | |
C2 | 0.12616 (14) | 0.3632 (3) | 0.24646 (10) | 0.0153 (4) | |
C3 | 0.17875 (14) | 0.2639 (3) | 0.18739 (10) | 0.0153 (4) | |
C4 | 0.28467 (15) | 0.3581 (3) | 0.17836 (11) | 0.0166 (5) | |
C5 | 0.33695 (15) | 0.5577 (4) | 0.22982 (11) | 0.0171 (5) | |
C6 | 0.28693 (13) | 0.6633 (3) | 0.29121 (10) | 0.0136 (4) | |
C7 | 0.34837 (13) | 0.8779 (3) | 0.34163 (10) | 0.0142 (5) | |
C8 | 0.33502 (14) | 0.9728 (3) | 0.41337 (11) | 0.0137 (4) | |
C9 | 0.25341 (14) | 0.8740 (3) | 0.46371 (10) | 0.0151 (5) | |
C10 | 0.14192 (15) | 1.0335 (3) | 0.44993 (12) | 0.0188 (5) | |
C11 | 0.40807 (13) | 1.2020 (3) | 0.44961 (10) | 0.0136 (4) | |
H1 | 0.14360 | 0.63037 | 0.33852 | 0.0183* | |
H2 | 0.05388 | 0.29637 | 0.25182 | 0.0183* | |
H4 | 0.32042 | 0.28747 | 0.13788 | 0.0199* | |
H5 | 0.40868 | 0.62513 | 0.22341 | 0.0205* | |
H7 | 0.40655 | 0.96284 | 0.32023 | 0.0170* | |
H9 | 0.29093 | 0.88527 | 0.52126 | 0.0181* | |
H9' | 0.23562 | 0.68362 | 0.45088 | 0.0181* | |
H10 | 0.15885 | 1.22220 | 0.46264 | 0.0281* | |
H10' | 0.09295 | 0.96348 | 0.48479 | 0.0281* | |
H10" | 0.10262 | 1.01680 | 0.39354 | 0.0281* | |
H11 | 0.517 (3) | 1.414 (7) | 0.4302 (19) | 0.053 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br | 0.0228 (1) | 0.0143 (1) | 0.0161 (1) | −0.0014 (1) | 0.0026 (1) | −0.0027 (1) |
O1 | 0.0158 (6) | 0.0185 (6) | 0.0209 (7) | −0.0061 (5) | 0.0064 (5) | −0.0031 (5) |
O2 | 0.0177 (6) | 0.0169 (6) | 0.0191 (6) | −0.0045 (5) | 0.0050 (5) | −0.0026 (5) |
C1 | 0.0146 (8) | 0.0158 (7) | 0.0157 (8) | 0.0014 (6) | 0.0042 (7) | −0.0003 (7) |
C2 | 0.0144 (7) | 0.0149 (8) | 0.0166 (8) | −0.0005 (6) | 0.0033 (7) | 0.0021 (6) |
C3 | 0.0185 (8) | 0.0115 (7) | 0.0147 (8) | 0.0000 (6) | 0.0010 (7) | −0.0005 (6) |
C4 | 0.0189 (8) | 0.0157 (8) | 0.0164 (8) | 0.0026 (6) | 0.0066 (7) | −0.0007 (6) |
C5 | 0.0154 (8) | 0.0176 (7) | 0.0195 (9) | −0.0006 (6) | 0.0063 (7) | 0.0014 (7) |
C6 | 0.0134 (7) | 0.0125 (7) | 0.0148 (8) | 0.0003 (6) | 0.0029 (6) | 0.0003 (6) |
C7 | 0.0094 (7) | 0.0139 (8) | 0.0191 (9) | −0.0007 (6) | 0.0028 (6) | 0.0024 (6) |
C8 | 0.0100 (7) | 0.0112 (7) | 0.0191 (9) | 0.0006 (5) | 0.0011 (7) | 0.0017 (6) |
C9 | 0.0154 (8) | 0.0143 (8) | 0.0155 (8) | −0.0016 (6) | 0.0029 (7) | 0.0002 (6) |
C10 | 0.0154 (8) | 0.0178 (8) | 0.0253 (10) | −0.0008 (6) | 0.0094 (8) | −0.0019 (7) |
C11 | 0.0102 (7) | 0.0126 (7) | 0.0176 (8) | 0.0016 (6) | 0.0018 (6) | 0.0031 (6) |
Geometric parameters (Å, º) top
Br—C3 | 1.9034 (16) | C8—C9 | 1.508 (2) |
O1—C11 | 1.330 (2) | C9—C10 | 1.532 (2) |
O2—C11 | 1.227 (2) | C1—H1 | 0.9500 |
O1—H11 | 0.79 (4) | C2—H2 | 0.9500 |
C1—C2 | 1.392 (2) | C4—H4 | 0.9500 |
C1—C6 | 1.405 (2) | C5—H5 | 0.9500 |
C2—C3 | 1.382 (2) | C7—H7 | 0.9500 |
C3—C4 | 1.391 (2) | C9—H9 | 0.9900 |
C4—C5 | 1.388 (3) | C9—H9' | 0.9900 |
C5—C6 | 1.408 (2) | C10—H10 | 0.9800 |
C6—C7 | 1.472 (2) | C10—H10' | 0.9800 |
C7—C8 | 1.348 (2) | C10—H10" | 0.9800 |
C8—C11 | 1.496 (2) | | |
| | | |
Br···C1i | 3.7246 (18) | C2···H2xi | 3.0600 |
Br···C6i | 3.7042 (17) | C4···H9iii | 2.9800 |
Br···C10ii | 3.7221 (18) | C6···H9' | 2.9000 |
Br···H10iii | 3.1600 | C8···H1 | 2.9300 |
Br···H10'iv | 3.1900 | C9···H1 | 2.5700 |
O1···C6v | 3.376 (2) | C10···H1 | 2.7700 |
O1···O2vi | 2.6716 (18) | C11···H10 | 3.0400 |
O2···C11vi | 3.3641 (19) | C11···H11vi | 2.81 (3) |
O2···C9v | 3.3219 (19) | H1···C8 | 2.9300 |
O2···O1vi | 2.6715 (18) | H1···C9 | 2.5700 |
O2···C10 | 3.307 (2) | H1···C10 | 2.7700 |
O1···H5vii | 2.9100 | H1···H9' | 2.0200 |
O1···H7 | 2.2800 | H1···H10" | 2.2400 |
O1···H9viii | 2.8100 | H2···C1xii | 2.9900 |
O2···H10 | 2.8200 | H2···C2xii | 3.0600 |
O2···H9 | 2.4800 | H4···O2iii | 2.5200 |
O2···H9'v | 2.7400 | H4···H9iii | 2.5400 |
O2···H11vi | 1.89 (3) | H5···H7 | 2.3600 |
O2···H4ix | 2.5200 | H5···O1xiii | 2.9100 |
C1···Brv | 3.7246 (18) | H7···O1 | 2.2800 |
C1···C9 | 3.180 (2) | H7···H5 | 2.3600 |
C1···C10 | 3.593 (2) | H9···O2 | 2.4800 |
C3···C6i | 3.587 (2) | H9···O1viii | 2.8100 |
C3···C7i | 3.539 (2) | H9···C4ix | 2.9800 |
C6···Brv | 3.7042 (17) | H9···H4ix | 2.5400 |
C6···O1i | 3.376 (2) | H9'···O2i | 2.7400 |
C6···C3v | 3.587 (2) | H9'···C1 | 2.6200 |
C7···C3v | 3.539 (2) | H9'···C6 | 2.9000 |
C8···C11viii | 3.564 (2) | H9'···H1 | 2.0200 |
C9···C1 | 3.180 (2) | H9'···H10i | 2.5100 |
C9···O2i | 3.3219 (19) | H10···O2 | 2.8200 |
C10···C1 | 3.593 (2) | H10···C11 | 3.0400 |
C10···O2 | 3.307 (2) | H10···H9'v | 2.5100 |
C10···Brx | 3.7221 (18) | H10···Brix | 3.1600 |
C11···C11viii | 3.211 (2) | H10'···H10'xiv | 2.4200 |
C11···O2vi | 3.3641 (19) | H10'···Brxv | 3.1900 |
C11···C8viii | 3.564 (2) | H10"···C1 | 3.0500 |
C1···H10" | 3.0500 | H10"···H1 | 2.2400 |
C1···H2xi | 2.9900 | H11···O2vi | 1.89 (3) |
C1···H9' | 2.6200 | H11···C11vi | 2.81 (3) |
| | | |
C11—O1—H11 | 110 (2) | C6—C1—H1 | 119.00 |
C2—C1—C6 | 121.15 (16) | C1—C2—H2 | 120.00 |
C1—C2—C3 | 119.50 (16) | C3—C2—H2 | 120.00 |
Br—C3—C2 | 118.83 (12) | C3—C4—H4 | 121.00 |
C2—C3—C4 | 121.38 (15) | C5—C4—H4 | 121.00 |
Br—C3—C4 | 119.78 (12) | C4—C5—H5 | 119.00 |
C3—C4—C5 | 118.52 (16) | C6—C5—H5 | 119.00 |
C4—C5—C6 | 122.03 (17) | C6—C7—H7 | 115.00 |
C1—C6—C5 | 117.41 (15) | C8—C7—H7 | 115.00 |
C5—C6—C7 | 117.79 (15) | C8—C9—H9 | 109.00 |
C1—C6—C7 | 124.77 (15) | C8—C9—H9' | 109.00 |
C6—C7—C8 | 130.13 (15) | C10—C9—H9 | 109.00 |
C7—C8—C11 | 118.28 (15) | C10—C9—H9' | 109.00 |
C9—C8—C11 | 114.23 (14) | H9—C9—H9' | 108.00 |
C7—C8—C9 | 127.49 (15) | C9—C10—H10 | 109.00 |
C8—C9—C10 | 112.92 (13) | C9—C10—H10' | 109.00 |
O1—C11—C8 | 116.16 (14) | C9—C10—H10" | 109.00 |
O2—C11—C8 | 121.63 (15) | H10—C10—H10' | 109.00 |
O1—C11—O2 | 122.22 (15) | H10—C10—H10" | 109.00 |
C2—C1—H1 | 119.00 | H10'—C10—H10" | 109.00 |
| | | |
C6—C1—C2—C3 | −0.2 (2) | C1—C6—C7—C8 | 18.6 (3) |
C2—C1—C6—C5 | 0.6 (2) | C5—C6—C7—C8 | −163.67 (18) |
C2—C1—C6—C7 | 178.30 (15) | C6—C7—C8—C9 | 2.3 (3) |
C1—C2—C3—Br | −179.19 (12) | C6—C7—C8—C11 | −177.88 (15) |
C1—C2—C3—C4 | 0.1 (2) | C7—C8—C9—C10 | −95.5 (2) |
Br—C3—C4—C5 | 178.74 (13) | C11—C8—C9—C10 | 84.67 (18) |
C2—C3—C4—C5 | −0.6 (2) | C7—C8—C11—O1 | −4.2 (2) |
C3—C4—C5—C6 | 1.1 (3) | C7—C8—C11—O2 | 175.82 (15) |
C4—C5—C6—C1 | −1.1 (3) | C9—C8—C11—O1 | 175.65 (14) |
C4—C5—C6—C7 | −178.93 (16) | C9—C8—C11—O2 | −4.4 (2) |
Symmetry codes: (i) x, y−1, z; (ii) −x, y−3/2, −z+1/2; (iii) x, −y+3/2, z−1/2; (iv) x, −y+1/2, z−1/2; (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, y−1/2, −z+1/2; (xiii) −x+1, y−1/2, −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···A | D—H | H···A | D···A | D—H···A |
O1—H11···O2vi | 0.79 (4) | 1.89 (3) | 2.6716 (18) | 172 (3) |
C4—H4···O2iii | 0.95 | 2.52 | 3.457 (2) | 167 |
C7—H7···O1 | 0.95 | 2.28 | 2.722 (2) | 107 |
Symmetry codes: (iii) x, −y+3/2, z−1/2; (vi) −x+1, −y+3, −z+1. |