4-Bromo­phenyl benzoate

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.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.011 Å
• R factor = 0.059
• wR factor = 0.190
• Data-to-parameter ratio = 9.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         11

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           66.93
           From the CIF: _reflns_number_total               1442
           Count of symmetry unique reflns         1067
           Completeness (_total/calc)            135.15%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       375
           Fraction of Friedel pairs measured     0.351
           Are heavy atom types Z>Si present        yes
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   2 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

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).

Related literature

For related literature, see: Adams & Morsi (1976); Gowda, Foro, Babitha & Fuess (2007); Gowda, Foro, Nayak & Fuess (2007); Nayak & Gowda (2008).

S2. Experimental

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.

S3. Refinement

The H atoms were positioned with idealized geometry using a riding model (C—H = 0.93 Å) with U_iso = 1.2 U_eq 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.

Computing details

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).

Figures

	Fig. 1. Molecular structure of the title compound, showing the atom labeling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of the title compound as viewed down the bc plane.

4-Bromophenyl benzoate

Crystal data

C13H9BrO2	F(000) = 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 = 9.9–23.4°
b = 5.5946 (7) Å	µ = 4.67 mm^−1
c = 26.814 (5) Å	T = 299 K
V = 1162.3 (3) Å^3	Plate, colourless
Z = 4	0.38 × 0.30 × 0.08 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	1252 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
Graphite monochromator	θmax = 66.9°, θmin = 3.3°
ω/2θ scans	h = −1→9
Absorption correction: ψ scan (North et al., 1968)	k = −1→6
Tmin = 0.242, Tmax = 0.685	l = −8→32
1986 measured reflections	3 standard reflections every 120 min
1442 independent reflections	intensity decay: 2.0%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.189	w = 1/[σ^2(Fo^2) + (0.1268P)^2 + 0.565P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max = 0.001
1442 reflections	Δρmax = 1.04 e Å^−3
145 parameters	Δρmin = −1.32 e Å^−3
1 restraint	Absolute structure: Flack (1983), with 375 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (6)

Special details

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 (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)