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In the title molecule, C
11H
11BrO
2, all bond lengths and angles show normal values. Weak intermolecular C—H
O hydrogen bonds link the molecules into centrosymmetric dimers and C—H
π interactions contribute to the stability of the crystal packing.
Supporting information
CCDC reference: 647175
Key indicators
- Single-crystal X-ray study
- T = 300 K
- Mean (C-C) = 0.005 Å
- R factor = 0.039
- wR factor = 0.108
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Explicit P-1
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 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: Bruker SMART (Bruker, 2000); cell refinement: Bruker SMART; data reduction: Bruker SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Bruker SHELXTL (Bruker, 1997); software used to prepare material for publication: Bruker SHELXTL.
(
E)-methyl 3-(3-(bromomethyl)phenyl)acrylate
top
Crystal data top
C11H11BrO2 | Z = 2 |
Mr = 255.11 | F(000) = 256 |
Triclinic, P1 | Dx = 1.573 Mg m−3 |
Hall symbol: P-1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.1578 (5) Å | Cell parameters from 2018 reflections |
b = 7.8390 (7) Å | θ = 2.8–26.6° |
c = 12.0604 (10) Å | µ = 3.79 mm−1 |
α = 77.580 (1)° | T = 300 K |
β = 88.816 (1)° | Block, colourless |
γ = 71.594 (1)° | 0.30 × 0.30 × 0.30 mm |
V = 538.76 (8) Å3 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1698 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.036 |
Graphite monochromator | θmax = 26.0°, θmin = 1.7° |
φ and ω scans | h = −7→7 |
4156 measured reflections | k = −9→9 |
2097 independent reflections | l = −14→14 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0484P)2 + 0.1854P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
2097 reflections | Δρmax = 0.54 e Å−3 |
129 parameters | Δρmin = −0.42 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.046 (5) |
Special details top
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 | x | y | z | Uiso*/Ueq | |
Br1 | 0.19380 (7) | 0.70764 (6) | 0.52839 (3) | 0.0782 (2) | |
C1 | −0.0273 (5) | 0.6062 (4) | 0.7310 (2) | 0.0477 (7) | |
C2 | 0.1331 (5) | 0.5216 (4) | 0.8212 (2) | 0.0455 (7) | |
H2 | 0.2517 | 0.5689 | 0.8283 | 0.055* | |
C3 | 0.1225 (5) | 0.3690 (4) | 0.9012 (2) | 0.0448 (7) | |
C4 | −0.0583 (6) | 0.3018 (5) | 0.8898 (3) | 0.0535 (7) | |
H4 | −0.0710 | 0.2008 | 0.9432 | 0.064* | |
C5 | −0.2186 (6) | 0.3837 (5) | 0.7999 (3) | 0.0603 (8) | |
H5 | −0.3377 | 0.3370 | 0.7929 | 0.072* | |
C6 | −0.2030 (5) | 0.5348 (5) | 0.7202 (3) | 0.0562 (8) | |
H6 | −0.3105 | 0.5886 | 0.6594 | 0.067* | |
C7 | −0.0143 (7) | 0.7731 (5) | 0.6492 (3) | 0.0635 (9) | |
H7A | 0.0394 | 0.8482 | 0.6893 | 0.076* | |
H7B | −0.1661 | 0.8453 | 0.6156 | 0.076* | |
C8 | 0.3008 (5) | 0.2856 (4) | 0.9935 (3) | 0.0481 (7) | |
H8 | 0.4175 | 0.3378 | 0.9910 | 0.058* | |
C9 | 0.3152 (6) | 0.1473 (4) | 1.0784 (3) | 0.0534 (7) | |
H9 | 0.2009 | 0.0921 | 1.0855 | 0.064* | |
C10 | 0.5086 (6) | 0.0768 (4) | 1.1633 (3) | 0.0512 (7) | |
C11 | 0.6559 (7) | −0.1336 (6) | 1.3357 (3) | 0.0710 (10) | |
H11A | 0.8014 | −0.1763 | 1.3031 | 0.107* | |
H11B | 0.6261 | −0.2355 | 1.3863 | 0.107* | |
H11C | 0.6586 | −0.0426 | 1.3772 | 0.107* | |
O1 | 0.6749 (4) | 0.1278 (4) | 1.1593 (2) | 0.0699 (7) | |
O2 | 0.4793 (4) | −0.0539 (3) | 1.2470 (2) | 0.0625 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0808 (3) | 0.0940 (4) | 0.0517 (3) | −0.0250 (2) | 0.01467 (19) | −0.00436 (19) |
C1 | 0.0470 (16) | 0.0541 (17) | 0.0398 (15) | −0.0110 (13) | 0.0060 (12) | −0.0141 (13) |
C2 | 0.0441 (15) | 0.0502 (17) | 0.0449 (16) | −0.0161 (13) | 0.0049 (12) | −0.0145 (13) |
C3 | 0.0441 (15) | 0.0500 (16) | 0.0406 (15) | −0.0116 (13) | 0.0034 (12) | −0.0154 (13) |
C4 | 0.0582 (18) | 0.0554 (18) | 0.0505 (17) | −0.0242 (15) | 0.0080 (14) | −0.0102 (14) |
C5 | 0.0520 (18) | 0.073 (2) | 0.066 (2) | −0.0291 (17) | 0.0050 (16) | −0.0235 (18) |
C6 | 0.0486 (17) | 0.072 (2) | 0.0449 (17) | −0.0113 (15) | −0.0044 (14) | −0.0185 (15) |
C7 | 0.070 (2) | 0.061 (2) | 0.0506 (19) | −0.0119 (17) | 0.0056 (16) | −0.0073 (15) |
C8 | 0.0492 (16) | 0.0482 (17) | 0.0481 (16) | −0.0153 (14) | 0.0060 (13) | −0.0140 (14) |
C9 | 0.0588 (19) | 0.0510 (18) | 0.0537 (18) | −0.0211 (15) | 0.0011 (15) | −0.0126 (14) |
C10 | 0.0607 (19) | 0.0444 (17) | 0.0461 (17) | −0.0112 (14) | −0.0009 (14) | −0.0131 (13) |
C11 | 0.080 (2) | 0.072 (2) | 0.050 (2) | −0.0200 (19) | −0.0038 (18) | 0.0038 (17) |
O1 | 0.0759 (17) | 0.0707 (16) | 0.0647 (16) | −0.0369 (14) | −0.0123 (13) | 0.0038 (12) |
O2 | 0.0651 (14) | 0.0657 (15) | 0.0549 (14) | −0.0264 (12) | −0.0035 (11) | −0.0004 (11) |
Geometric parameters (Å, º) top
Br1—C7 | 1.964 (3) | C7—H7A | 0.9700 |
C1—C6 | 1.385 (5) | C7—H7B | 0.9700 |
C1—C2 | 1.386 (4) | C8—C9 | 1.303 (5) |
C1—C7 | 1.483 (5) | C8—H8 | 0.9300 |
C2—C3 | 1.385 (4) | C9—C10 | 1.471 (5) |
C2—H2 | 0.9300 | C9—H9 | 0.9300 |
C3—C4 | 1.394 (4) | C10—O1 | 1.208 (4) |
C3—C8 | 1.468 (4) | C10—O2 | 1.329 (4) |
C4—C5 | 1.380 (5) | C11—O2 | 1.431 (4) |
C4—H4 | 0.9300 | C11—H11A | 0.9600 |
C5—C6 | 1.384 (5) | C11—H11B | 0.9600 |
C5—H5 | 0.9300 | C11—H11C | 0.9600 |
C6—H6 | 0.9300 | | |
| | | |
C6—C1—C2 | 118.9 (3) | Br1—C7—H7A | 109.4 |
C6—C1—C7 | 120.7 (3) | C1—C7—H7B | 109.4 |
C2—C1—C7 | 120.4 (3) | Br1—C7—H7B | 109.4 |
C3—C2—C1 | 122.1 (3) | H7A—C7—H7B | 108.0 |
C3—C2—H2 | 118.9 | C9—C8—C3 | 127.9 (3) |
C1—C2—H2 | 118.9 | C9—C8—H8 | 116.1 |
C2—C3—C4 | 118.0 (3) | C3—C8—H8 | 116.1 |
C2—C3—C8 | 118.9 (3) | C8—C9—C10 | 121.4 (3) |
C4—C3—C8 | 123.2 (3) | C8—C9—H9 | 119.3 |
C5—C4—C3 | 120.6 (3) | C10—C9—H9 | 119.3 |
C5—C4—H4 | 119.7 | O1—C10—O2 | 123.1 (3) |
C3—C4—H4 | 119.7 | O1—C10—C9 | 125.6 (3) |
C4—C5—C6 | 120.4 (3) | O2—C10—C9 | 111.2 (3) |
C4—C5—H5 | 119.8 | O2—C11—H11A | 109.5 |
C6—C5—H5 | 119.8 | O2—C11—H11B | 109.5 |
C5—C6—C1 | 120.0 (3) | H11A—C11—H11B | 109.5 |
C5—C6—H6 | 120.0 | O2—C11—H11C | 109.5 |
C1—C6—H6 | 120.0 | H11A—C11—H11C | 109.5 |
C1—C7—Br1 | 111.2 (2) | H11B—C11—H11C | 109.5 |
C1—C7—H7A | 109.4 | C10—O2—C11 | 116.7 (3) |
| | | |
C6—C1—C2—C3 | −0.4 (4) | C6—C1—C7—Br1 | −96.3 (3) |
C7—C1—C2—C3 | 178.0 (3) | C2—C1—C7—Br1 | 85.3 (3) |
C1—C2—C3—C4 | −0.7 (4) | C2—C3—C8—C9 | 177.1 (3) |
C1—C2—C3—C8 | 179.2 (2) | C4—C3—C8—C9 | −3.0 (5) |
C2—C3—C4—C5 | 1.2 (4) | C3—C8—C9—C10 | 178.7 (3) |
C8—C3—C4—C5 | −178.7 (3) | C8—C9—C10—O1 | −5.4 (5) |
C3—C4—C5—C6 | −0.5 (5) | C8—C9—C10—O2 | 174.9 (3) |
C4—C5—C6—C1 | −0.7 (5) | O1—C10—O2—C11 | 0.6 (5) |
C2—C1—C6—C5 | 1.2 (4) | C9—C10—O2—C11 | −179.7 (3) |
C7—C1—C6—C5 | −177.2 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1i | 0.93 | 2.59 | 3.369 (4) | 141 |
C11—H11A···Cgii | 0.96 | 2.82 | 3.6048 | 140 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y+2, −z. |
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