4-Methyl­phenyl 4-bromo­benzoate

Moreno-Fuquen, R.; Ellena, J.; De Simone, C.A.

doi:10.1107/S1600536811040426

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2869

doi:10.1107/S1600536811040426

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4-Methylphenyl 4-bromobenzoate

Rodolfo Moreno-Fuquen,^a ^* Javier Ellena ^b and Carlos A. De Simone ^b

^aDepartamento de Química – Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia, and ^bInstituto de Física, IFSC, Universidade de São Paulo, São Carlos, Brazil
^*Correspondence e-mail: rodimo26@yahoo.es

(Received 29 September 2011; accepted 30 September 2011; online 8 October 2011)

In the title compound, C₁₄H₁₁BrO₂, an ester formed from the reaction of 4-methylphenol with 4-bromobenzoylchloride, the dihedral angle between the benzene rings is 54.43 (7)°, indicating a twist in the molecule. In the crystal, weak C—H⋯O interactions link the molecules into supramolecular layers in the bc plane, and these are connected along the a axis by Br⋯Br contacts [3.6328 (5) Å].

Related literature

For industrial applications of ester systems, see: Gowda et al. (2007a ); Brüning et al. (2009 ). For related structures, see: Gowda et al. (2007b , 2008 ). For hydrogen bonding, see: Nardelli (1995 ). For halogen interactions, see: Ritter (2009 ).

Experimental

Crystal data

C₁₄H₁₁BrO₂
M_r = 291.13
Monoclinic, P 2₁ /c
a = 15.0219 (9) Å
b = 11.3585 (8) Å
c = 7.5077 (4) Å
β = 99.730 (4)°
V = 1262.58 (14) Å³
Z = 4
Mo Kα radiation
μ = 3.24 mm⁻¹
T = 293 K
0.47 × 0.18 × 0.10 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.472, T_max = 0.698
9090 measured reflections
2829 independent reflections
1811 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.125
S = 1.01
2829 reflections
156 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.93	2.67	3.483 (4)	147
C13—H13⋯O1ⁱⁱ	0.93	2.77	3.422 (4)	128
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 2004 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PARST (Nardelli, 1995).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811040426/tk2795sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811040426/tk2795Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811040426/tk2795Isup3.cml

checkCIF report

Comment top

This work is part of the study of the effect of substituents on the ester system. Similar work, involving ester systems with an emphasis on industrial applications has been published (Gowda et al., 2007a; Brüning et al., 2009). The molecular structure of the title compound (I) is similar to that of 4-bromophenyl benzoate (4BPB) (Gowda et al., 2008) and 4-methylphenyl 4-methylbenzoate (4MPB) (Gowda et al., 2007b). Compound (I) shows a dihedral angle of 54.43 (7)° between the mean planes of the benzene rings (Fig. 1). This dihedral angle is close to the values presented in the 4BPB and 4MPB molecules [58.43 (17) and 60.17 (7)°, respectively].

The crystal packing is stabilized by C—H···O interactions (Nardelli, 1995); Table 1. These weak interactions link the molecules into supramolecular layers in the bc plane. The layers are connected by Br···Br interactions (Ritter, 2009).

Related literature top

For industrial applications of ester systems, see: Gowda et al. (2007a); Brüning et al. (2009). For related structures, see: Gowda et al. (2007b, 2008). For hydrogen bonding, see: Nardelli (1995). For halogen interactions, see: Ritter (2009).

Experimental top

A solution containing equimolar quantities (3.4 mmol) of 4-bromobenzoyl chloride and 4-methylphenol in acetonitrile (60 ml) was gradually heated to reflux for 2 h and then allowed to cool. At room temperature, triethylamine was added to get a solid which was poured in cold water. The solid was recrystallized from its dichlorometane solution to yield colourless crystals; M.pt. 385 (1) K.

Computing details top

Data collection: COLLECT (Nonius, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

Figures top

Fig. 1. Molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.

4-Methylphenyl 4-bromobenzoate top

Crystal data top

C₁₄H₁₁BrO₂	F(000) = 584
M_r = 291.13	D_x = 1.532 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 385(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.0219 (9) Å	Cell parameters from 9005 reflections
b = 11.3585 (8) Å	θ = 2.9–27.5°
c = 7.5077 (4) Å	µ = 3.24 mm⁻¹
β = 99.730 (4)°	T = 293 K
V = 1262.58 (14) Å³	Prism, colourless
Z = 4	0.47 × 0.18 × 0.10 mm

Data collection top

Bruker–Nonius KappaCCD diffractometer	2829 independent reflections
Radiation source: fine-focus sealed tube	1811 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromator	R_int = 0.052
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 3.7°
CCD scans	h = −19→19
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→10
T_min = 0.472, T_max = 0.698	l = −9→9
9090 measured reflections

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.125	w = 1/[σ²(F_o²) + (0.0577P)² + 0.3548P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2829 reflections	Δρ_max = 0.31 e Å⁻³
156 parameters	Δρ_min = −0.36 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (3)

Crystal data top

C₁₄H₁₁BrO₂	V = 1262.58 (14) Å³
M_r = 291.13	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.0219 (9) Å	µ = 3.24 mm⁻¹
b = 11.3585 (8) Å	T = 293 K
c = 7.5077 (4) Å	0.47 × 0.18 × 0.10 mm
β = 99.730 (4)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	2829 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1811 reflections with I > 2σ(I)
T_min = 0.472, T_max = 0.698	R_int = 0.052
9090 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.01	Δρ_max = 0.31 e Å⁻³
2829 reflections	Δρ_min = −0.36 e Å⁻³
156 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	U_iso*/U_eq
Br1	0.61020 (2)	0.93326 (4)	0.00395 (6)	0.0970 (2)
C14	1.4444 (2)	0.8443 (4)	0.4571 (6)	0.1050 (13)
H14A	1.4685	0.8902	0.5615	0.158*
H14B	1.4718	0.8687	0.3564	0.158*
H14C	1.4572	0.7625	0.4817	0.158*
O2	1.06435 (14)	0.91018 (16)	0.2775 (3)	0.0640 (5)
O1	1.02822 (15)	0.7422 (2)	0.4071 (3)	0.0864 (7)
C5	0.8438 (2)	0.7772 (2)	0.2633 (4)	0.0615 (7)
H5	0.8594	0.7079	0.3270	0.074*
C1	0.7324 (2)	0.9019 (3)	0.0998 (4)	0.0631 (7)
C3	0.8867 (2)	0.9613 (2)	0.1444 (4)	0.0590 (6)
H3	0.9309	1.0156	0.1275	0.071*
C2	0.7978 (2)	0.9834 (3)	0.0749 (4)	0.0619 (7)
H2	0.7815	1.0526	0.0116	0.074*
C8	1.15716 (19)	0.8889 (2)	0.3280 (3)	0.0558 (6)
C7	1.0054 (2)	0.8281 (3)	0.3177 (4)	0.0617 (7)
C4	0.91105 (18)	0.8576 (2)	0.2403 (3)	0.0545 (6)
C6	0.7555 (2)	0.7987 (3)	0.1938 (4)	0.0663 (7)
H6	0.7111	0.7444	0.2095	0.080*
C11	1.3432 (2)	0.8623 (3)	0.4124 (4)	0.0723 (8)
C13	1.1971 (2)	0.7893 (2)	0.2718 (4)	0.0641 (7)
H13	1.1624	0.7313	0.2056	0.077*
C9	1.2087 (2)	0.9753 (3)	0.4252 (4)	0.0636 (7)
H9	1.1814	1.0422	0.4630	0.076*
C12	1.2891 (2)	0.7777 (3)	0.3156 (4)	0.0710 (8)
H12	1.3161	0.7103	0.2789	0.085*
C10	1.3008 (2)	0.9615 (3)	0.4656 (4)	0.0720 (8)
H10	1.3355	1.0202	0.5302	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0691 (3)	0.1091 (4)	0.1086 (4)	0.00332 (19)	0.00328 (19)	0.0103 (2)
C14	0.067 (2)	0.107 (3)	0.140 (3)	0.002 (2)	0.014 (2)	0.004 (3)
O2	0.0677 (12)	0.0511 (11)	0.0726 (11)	0.0013 (9)	0.0099 (9)	0.0076 (9)
O1	0.0789 (14)	0.0797 (15)	0.0998 (15)	0.0048 (12)	0.0129 (11)	0.0395 (13)
C5	0.0802 (19)	0.0442 (14)	0.0603 (14)	−0.0036 (13)	0.0130 (13)	0.0073 (11)
C1	0.0668 (16)	0.0635 (17)	0.0598 (15)	0.0025 (14)	0.0127 (12)	−0.0013 (13)
C3	0.0727 (17)	0.0450 (14)	0.0630 (14)	−0.0011 (12)	0.0221 (13)	0.0035 (11)
C2	0.0724 (17)	0.0500 (15)	0.0656 (15)	0.0088 (14)	0.0187 (13)	0.0065 (13)
C8	0.0665 (16)	0.0492 (14)	0.0530 (13)	0.0001 (12)	0.0137 (11)	0.0047 (11)
C7	0.0760 (18)	0.0527 (15)	0.0577 (14)	−0.0008 (14)	0.0145 (12)	0.0066 (13)
C4	0.0695 (16)	0.0446 (14)	0.0507 (13)	0.0012 (12)	0.0141 (11)	0.0017 (10)
C6	0.0751 (18)	0.0569 (17)	0.0677 (15)	−0.0106 (14)	0.0144 (13)	0.0014 (13)
C11	0.0743 (18)	0.066 (2)	0.0790 (18)	0.0034 (15)	0.0196 (15)	0.0049 (15)
C13	0.0816 (19)	0.0510 (15)	0.0596 (14)	0.0004 (14)	0.0118 (13)	−0.0032 (12)
C9	0.0733 (18)	0.0506 (15)	0.0700 (16)	−0.0020 (14)	0.0212 (13)	−0.0066 (13)
C12	0.086 (2)	0.0580 (17)	0.0729 (17)	0.0097 (16)	0.0240 (15)	−0.0012 (14)
C10	0.078 (2)	0.0616 (18)	0.0766 (18)	−0.0107 (15)	0.0145 (15)	−0.0076 (14)

Geometric parameters (Å, º) top

Br1—C1	1.889 (3)	C3—H3	0.9300
C14—C11	1.515 (5)	C2—H2	0.9300
C14—H14A	0.9600	C8—C9	1.380 (4)
C14—H14B	0.9600	C8—C13	1.380 (4)
C14—H14C	0.9600	C7—C4	1.477 (4)
O2—C7	1.355 (3)	C6—H6	0.9300
O2—C8	1.402 (3)	C11—C10	1.386 (5)
O1—C7	1.200 (3)	C11—C12	1.383 (5)
C5—C6	1.363 (4)	C13—C12	1.372 (4)
C5—C4	1.394 (4)	C13—H13	0.9300
C5—H5	0.9300	C9—C10	1.375 (4)
C1—C6	1.382 (4)	C9—H9	0.9300
C1—C2	1.384 (4)	C12—H12	0.9300
C3—C2	1.373 (4)	C10—H10	0.9300
C3—C4	1.397 (4)

C11—C14—H14A	109.5	O1—C7—C4	124.7 (3)
C11—C14—H14B	109.5	O2—C7—C4	112.1 (2)
H14A—C14—H14B	109.5	C5—C4—C3	119.0 (3)
C11—C14—H14C	109.5	C5—C4—C7	118.0 (2)
H14A—C14—H14C	109.5	C3—C4—C7	123.0 (2)
H14B—C14—H14C	109.5	C5—C6—C1	119.4 (3)
C7—O2—C8	118.6 (2)	C5—C6—H6	120.3
C6—C5—C4	120.9 (3)	C1—C6—H6	120.3
C6—C5—H5	119.6	C10—C11—C12	117.3 (3)
C4—C5—H5	119.6	C10—C11—C14	122.6 (3)
C6—C1—C2	120.9 (3)	C12—C11—C14	120.1 (3)
C6—C1—Br1	119.9 (2)	C12—C13—C8	118.5 (3)
C2—C1—Br1	119.2 (2)	C12—C13—H13	120.7
C2—C3—C4	120.2 (3)	C8—C13—H13	120.7
C2—C3—H3	119.9	C10—C9—C8	119.3 (3)
C4—C3—H3	119.9	C10—C9—H9	120.3
C3—C2—C1	119.6 (3)	C8—C9—H9	120.3
C3—C2—H2	120.2	C13—C12—C11	122.6 (3)
C1—C2—H2	120.2	C13—C12—H12	118.7
C9—C8—C13	120.7 (3)	C11—C12—H12	118.7
C9—C8—O2	117.6 (2)	C9—C10—C11	121.6 (3)
C13—C8—O2	121.5 (3)	C9—C10—H10	119.2
O1—C7—O2	123.3 (3)	C11—C10—H10	119.2

C4—C3—C2—C1	−0.3 (4)	O2—C7—C4—C3	−2.8 (4)
C6—C1—C2—C3	0.1 (4)	C4—C5—C6—C1	−0.2 (4)
Br1—C1—C2—C3	179.9 (2)	C2—C1—C6—C5	0.2 (4)
C7—O2—C8—C9	−128.0 (3)	Br1—C1—C6—C5	−179.6 (2)
C7—O2—C8—C13	56.6 (3)	C9—C8—C13—C12	0.4 (4)
C8—O2—C7—O1	6.1 (4)	O2—C8—C13—C12	175.6 (2)
C8—O2—C7—C4	−174.3 (2)	C13—C8—C9—C10	0.2 (4)
C6—C5—C4—C3	0.0 (4)	O2—C8—C9—C10	−175.2 (2)
C6—C5—C4—C7	−179.4 (2)	C8—C13—C12—C11	−0.6 (4)
C2—C3—C4—C5	0.3 (4)	C10—C11—C12—C13	0.2 (5)
C2—C3—C4—C7	179.7 (2)	C14—C11—C12—C13	179.8 (3)
O1—C7—C4—C5	−3.8 (4)	C8—C9—C10—C11	−0.6 (5)
O2—C7—C4—C5	176.6 (2)	C12—C11—C10—C9	0.4 (5)
O1—C7—C4—C3	176.7 (3)	C14—C11—C10—C9	−179.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.93	2.67	3.483 (4)	147
C13—H13···O1ⁱⁱ	0.93	2.77	3.422 (4)	128

Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁BrO₂
M_r	291.13
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	15.0219 (9), 11.3585 (8), 7.5077 (4)
β (°)	99.730 (4)
V (Å³)	1262.58 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.24
Crystal size (mm)	0.47 × 0.18 × 0.10

Data collection
Diffractometer	Bruker–Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.472, 0.698
No. of measured, independent and observed [I > 2σ(I)] reflections	9090, 2829, 1811
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.125, 1.01
No. of reflections	2829
No. of parameters	156
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.36

Computer programs: COLLECT (Nonius, 2004), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.93	2.67	3.483 (4)	146.5
C13—H13···O1ⁱⁱ	0.93	2.77	3.422 (4)	128.4

Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) x, −y+3/2, z−1/2.

Acknowledgements

RMF is grateful to the Spanish Research Council (CSIC) for the use of a free-of-charge licence to the Cambridge Structural Database (Allen, 2002 ). RMF also thank the Universidad del Valle, Colombia, for partial financial support.

References

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