Acta Cryst. (2008). E64, o771 [ doi:10.1107/S1600536808008167 ]
The structure of the title compound (4BPBA), C13H9BrO2, is similar to that of phenyl benzoate (PBA), 4-methylphenyl benzoate (4MePBA) and 4-methoxyphenyl benzoate, with somewhat different bond parameters. The dihedral angle between the phenyl and benzoyl rings in 4BPBA is 58.43 (17)°, compared with values of 55.7° in PBA and 60.17 (7)° in 4MPBA. The molecules in the title compound are packed into infinite chains in the a-axis direction.
The title compound was prepared according to a literature method (Nayak & Gowda, 2008). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Nayak & Gowda, 2008). Single crystals of the title compound were obtained by slow evaporation of an ethanolic solution and used for X-ray diffraction studies at room temperature.
The H atoms were positioned with idealized geometry using a riding model (C—H = 0.93 Å) with Uiso = 1.2 Ueq of the parent atom.
The residual electron-density features are located in the region of Br1. The highest peak is 0.91 Å from C4 and deepest hole is 0.78 Å from Br1.
Data collection: CAD-4-PC Software (Enraf–Nonius, 1996); cell refinement: CAD-4-PC Software (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./om2221fig1thm.gif)
| Fig. 1. Molecular structure of the title compound, showing the atom labeling. Displacement ellipsoids are drawn at the 50% probability level. |
![[Figure 2]](./om2221fig2thm.gif)
| Fig. 2. Molecular packing of the title compound as viewed down the bc plane. |
| C13H9BrO2 | F000 = 552 |
| Mr = 277.11 | Dx = 1.584 Mg m−3 |
| Orthorhombic, Pca21 | Cu Kα radiation λ = 1.54180 Å |
| Hall symbol: P 2c -2ac | Cell parameters from 25 reflections |
| a = 7.748 (1) Å | θ = 9.9–23.4º |
| b = 5.5946 (7) Å | µ = 4.67 mm−1 |
| c = 26.814 (5) Å | T = 299 (2) K |
| V = 1162.3 (3) Å3 | Plate, colourless |
| Z = 4 | 0.38 × 0.30 × 0.08 mm |
| Enraf–Nonius CAD-4 diffractometer | Rint = 0.039 |
| Radiation source: fine-focus sealed tube | θmax = 66.9º |
| Monochromator: graphite | θmin = 3.3º |
| T = 299(2) K | h = −1→9 |
| ω/2θ scans | k = −1→6 |
| Absorption correction: ψ scan (North et al., 1968) | l = −8→32 |
| Tmin = 0.242, Tmax = 0.685 | 3 standard reflections |
| 1986 measured reflections | every 120 min |
| 1442 independent reflections | intensity decay: 2.0% |
| 1252 reflections with I > 2σ(I) |
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.059 | w = 1/[σ2(Fo2) + (0.1268P)2 + 0.565P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.189 | (Δ/σ)max = 0.001 |
| S = 1.15 | Δρmax = 1.04 e Å−3 |
| 1442 reflections | Δρmin = −1.32 e Å−3 |
| 145 parameters | Extinction correction: none |
| 1 restraint | Absolute structure: Flack (1983), with 375 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Flack parameter: −0.04 (6) |
| Secondary atom site location: difference Fourier map |
| C13H9BrO2 | V = 1162.3 (3) Å3 |
| Mr = 277.11 | Z = 4 |
| Orthorhombic, Pca21 | Cu Kα |
| a = 7.748 (1) Å | µ = 4.67 mm−1 |
| b = 5.5946 (7) Å | T = 299 (2) K |
| c = 26.814 (5) Å | 0.38 × 0.30 × 0.08 mm |
| Enraf–Nonius CAD-4 diffractometer | 1252 reflections with I > 2σ(I) |
| Absorption correction: ψ scan (North et al., 1968) | Rint = 0.039 |
| Tmin = 0.242, Tmax = 0.685 | 3 standard reflections |
| 1986 measured reflections | every 120 min |
| 1442 independent reflections | intensity decay: 2.0% |
| R[F2 > 2σ(F2)] = 0.059 | H-atom parameters constrained |
| wR(F2) = 0.189 | Δρmax = 1.04 e Å−3 |
| S = 1.15 | Δρmin = −1.32 e Å−3 |
| 1442 reflections | Absolute structure: Flack (1983), with 375 Friedel pairs |
| 145 parameters | Flack parameter: −0.04 (6) |
| 1 restraint |
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. |
| x | y | z | Uiso*/Ueq | ||
| Br1 | 0.29159 (16) | 0.2659 (2) | −0.12742 (8) | 0.0950 (5) | |
| O1 | 0.4692 (6) | 0.1882 (9) | 0.0901 (2) | 0.0581 (13) | |
| O2 | 0.3231 (11) | 0.5195 (14) | 0.1104 (3) | 0.107 (3) | |
| C1 | 0.4260 (8) | 0.2190 (10) | 0.0403 (3) | 0.0463 (14) | |
| C2 | 0.4854 (8) | 0.4121 (12) | 0.0127 (3) | 0.0544 (16) | |
| H2 | 0.5500 | 0.5321 | 0.0278 | 0.065* | |
| C3 | 0.4478 (8) | 0.4229 (12) | −0.0367 (3) | 0.0560 (17) | |
| H3 | 0.4888 | 0.5492 | −0.0559 | 0.067* | |
| C4 | 0.3474 (11) | 0.2440 (12) | −0.0586 (3) | 0.0559 (17) | |
| C5 | 0.2920 (9) | 0.0437 (12) | −0.0313 (3) | 0.0589 (18) | |
| H5 | 0.2301 | −0.0794 | −0.0462 | 0.071* | |
| C6 | 0.3332 (9) | 0.0389 (13) | 0.0176 (3) | 0.0583 (17) | |
| H6 | 0.2977 | −0.0908 | 0.0368 | 0.070* | |
| C7 | 0.4106 (9) | 0.3510 (14) | 0.1226 (3) | 0.0577 (17) | |
| C8 | 0.4601 (9) | 0.2976 (12) | 0.1748 (3) | 0.0521 (15) | |
| C9 | 0.5527 (8) | 0.0900 (13) | 0.1879 (3) | 0.0585 (17) | |
| H9 | 0.5846 | −0.0209 | 0.1638 | 0.070* | |
| C10 | 0.5943 (10) | 0.0558 (13) | 0.2368 (4) | 0.0644 (19) | |
| H10 | 0.6544 | −0.0820 | 0.2454 | 0.077* | |
| C11 | 0.5530 (10) | 0.2107 (14) | 0.2731 (4) | 0.0627 (19) | |
| H11 | 0.5834 | 0.1803 | 0.3060 | 0.075* | |
| C12 | 0.4636 (9) | 0.4180 (14) | 0.2604 (3) | 0.0602 (17) | |
| H12 | 0.4353 | 0.5284 | 0.2851 | 0.072* | |
| C13 | 0.4164 (9) | 0.4607 (13) | 0.2112 (3) | 0.0585 (16) | |
| H13 | 0.3558 | 0.5985 | 0.2029 | 0.070* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Br1 | 0.1056 (8) | 0.1322 (9) | 0.0472 (6) | 0.0167 (6) | −0.0058 (7) | −0.0056 (7) |
| O1 | 0.053 (2) | 0.064 (3) | 0.058 (3) | 0.008 (2) | −0.003 (2) | −0.011 (3) |
| O2 | 0.145 (6) | 0.117 (5) | 0.059 (4) | 0.089 (5) | 0.005 (4) | 0.001 (4) |
| C1 | 0.044 (3) | 0.047 (3) | 0.049 (4) | 0.003 (2) | −0.001 (3) | −0.003 (3) |
| C2 | 0.046 (3) | 0.052 (3) | 0.066 (5) | −0.007 (3) | 0.004 (3) | −0.009 (3) |
| C3 | 0.055 (3) | 0.052 (3) | 0.061 (5) | 0.007 (3) | 0.011 (3) | 0.005 (3) |
| C4 | 0.058 (4) | 0.067 (4) | 0.042 (4) | 0.006 (3) | 0.005 (4) | −0.006 (3) |
| C5 | 0.062 (4) | 0.049 (3) | 0.066 (5) | −0.004 (3) | −0.005 (4) | −0.006 (3) |
| C6 | 0.054 (3) | 0.058 (4) | 0.063 (5) | −0.012 (3) | 0.002 (4) | 0.010 (4) |
| C7 | 0.050 (3) | 0.068 (4) | 0.055 (4) | 0.019 (3) | 0.004 (3) | 0.002 (4) |
| C8 | 0.051 (3) | 0.055 (3) | 0.050 (4) | −0.005 (3) | 0.006 (3) | −0.001 (3) |
| C9 | 0.053 (3) | 0.062 (3) | 0.061 (4) | 0.017 (3) | −0.004 (3) | −0.010 (4) |
| C10 | 0.057 (3) | 0.062 (4) | 0.074 (5) | 0.007 (3) | −0.008 (4) | 0.015 (4) |
| C11 | 0.056 (3) | 0.082 (5) | 0.050 (5) | −0.001 (3) | −0.002 (3) | 0.003 (4) |
| C12 | 0.064 (4) | 0.065 (4) | 0.052 (4) | −0.007 (3) | 0.005 (4) | −0.002 (4) |
| C13 | 0.056 (3) | 0.059 (4) | 0.060 (4) | 0.010 (3) | −0.003 (3) | 0.001 (3) |
| Br1—C4 | 1.899 (9) | C6—H6 | 0.9300 |
| O1—C7 | 1.340 (10) | C7—C8 | 1.481 (12) |
| O1—C1 | 1.388 (10) | C8—C13 | 1.379 (11) |
| O2—C7 | 1.206 (9) | C8—C9 | 1.410 (10) |
| C1—C6 | 1.379 (10) | C9—C10 | 1.364 (12) |
| C1—C2 | 1.388 (10) | C9—H9 | 0.9300 |
| C2—C3 | 1.356 (12) | C10—C11 | 1.342 (12) |
| C2—H2 | 0.9300 | C10—H10 | 0.9300 |
| C3—C4 | 1.398 (11) | C11—C12 | 1.392 (11) |
| C3—H3 | 0.9300 | C11—H11 | 0.9300 |
| C4—C5 | 1.406 (11) | C12—C13 | 1.390 (12) |
| C5—C6 | 1.351 (12) | C12—H12 | 0.9300 |
| C5—H5 | 0.9300 | C13—H13 | 0.9300 |
| C7—O1—C1 | 117.4 (5) | O2—C7—C8 | 124.1 (7) |
| C6—C1—C2 | 120.4 (8) | O1—C7—C8 | 112.9 (6) |
| C6—C1—O1 | 117.3 (6) | C13—C8—C9 | 119.5 (8) |
| C2—C1—O1 | 122.0 (6) | C13—C8—C7 | 118.2 (6) |
| C3—C2—C1 | 118.9 (6) | C9—C8—C7 | 122.2 (7) |
| C3—C2—H2 | 120.5 | C10—C9—C8 | 118.4 (7) |
| C1—C2—H2 | 120.5 | C10—C9—H9 | 120.8 |
| C2—C3—C4 | 119.9 (7) | C8—C9—H9 | 120.8 |
| C2—C3—H3 | 120.1 | C11—C10—C9 | 123.4 (7) |
| C4—C3—H3 | 120.1 | C11—C10—H10 | 118.3 |
| C3—C4—C5 | 121.4 (8) | C9—C10—H10 | 118.3 |
| C3—C4—Br1 | 119.3 (6) | C10—C11—C12 | 118.7 (8) |
| C5—C4—Br1 | 119.2 (6) | C10—C11—H11 | 120.7 |
| C6—C5—C4 | 116.7 (7) | C12—C11—H11 | 120.7 |
| C6—C5—H5 | 121.6 | C13—C12—C11 | 120.4 (8) |
| C4—C5—H5 | 121.6 | C13—C12—H12 | 119.8 |
| C5—C6—C1 | 122.4 (7) | C11—C12—H12 | 119.8 |
| C5—C6—H6 | 118.8 | C8—C13—C12 | 119.6 (7) |
| C1—C6—H6 | 118.8 | C8—C13—H13 | 120.2 |
| O2—C7—O1 | 123.0 (8) | C12—C13—H13 | 120.2 |
| C7—O1—C1—C6 | −120.1 (7) | C1—O1—C7—C8 | 178.5 (6) |
| C7—O1—C1—C2 | 65.4 (9) | O2—C7—C8—C13 | −5.8 (12) |
| C6—C1—C2—C3 | 1.3 (10) | O1—C7—C8—C13 | 175.9 (6) |
| O1—C1—C2—C3 | 175.6 (6) | O2—C7—C8—C9 | 175.6 (9) |
| C1—C2—C3—C4 | 1.4 (10) | O1—C7—C8—C9 | −2.7 (10) |
| C2—C3—C4—C5 | −3.8 (10) | C13—C8—C9—C10 | 0.9 (10) |
| C2—C3—C4—Br1 | 178.5 (5) | C7—C8—C9—C10 | 179.5 (7) |
| C3—C4—C5—C6 | 3.2 (10) | C8—C9—C10—C11 | −0.6 (12) |
| Br1—C4—C5—C6 | −179.1 (6) | C9—C10—C11—C12 | −0.3 (12) |
| C4—C5—C6—C1 | −0.5 (11) | C10—C11—C12—C13 | 0.9 (11) |
| C2—C1—C6—C5 | −1.8 (11) | C9—C8—C13—C12 | −0.3 (11) |
| O1—C1—C6—C5 | −176.4 (7) | C7—C8—C13—C12 | −178.9 (7) |
| C1—O1—C7—O2 | 0.2 (12) | C11—C12—C13—C8 | −0.6 (11) |
BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions to his research fellowship.
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In the present work, the structure of 4-bromophenyl benzoate (4BPBA) has been determined, as part of a study of substituent effects on the structures of industrially significant compounds (Gowda, Foro, Babitha & Fuess, 2007; Gowda, Foro, Nayak & Fuess, 2007). The structure of 4BPBA (Fig. 1) resembles those of phenyl benzoate (PBA) (Adams & Morsi, 1976), 4-methylphenyl benzoate (4MePBA), 4-methoxyphenyl benzoate (4MeOPBA), 3-methylphenyl benzoate (3MePBA), 2,3-dichlorophenyl benzoate (23DCPBA) and other aryl benzoates (Gowda, Foro, Babitha & Fuess, 2007; Gowda, Foro, Nayak & Fuess, 2007). The bond parameters in 4BPBA are similar to those in PBA, 4MePBA, 4MeOPBA, 3MePBA, 23DCPBA and other benzoates (Adams & Morsi, 1976; Gowda, Foro, Babitha & Fuess, 2007; Gowda, Foro, Nayak & Fuess, 2007). The molecules in the title compound are packed into chains in the bc plane (Fig. 2).