4-Methyl­phenyl 4-chloro­benzoate

Gowda, B.T.; Svoboda, I.; Babitha, K.S.; Fuess, H.

doi:10.1107/S1600536807062137

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o88

https://doi.org/10.1107/S1600536807062137

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4-Methylphenyl 4-chlorobenzoate

B. Thimme Gowda,^a ^* Ingrid Svoboda,^b K. S. Babitha ^a and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 21 November 2007; accepted 22 November 2007; online 6 December 2007)

The crystal structure of the title compound, C₁₄H₁₁ClO₂, is similar to those of phenyl benzoate, 4-methylphenyl benzoate and 4-methylphenyl 4-methylbenzoate. The dihedral angle between the phenyl and benzene rings is 51.86 (4)°. The molecules crystallize in planes parallel to ( $[\overline{1}]$ 02).

Related literature

For related literature, see: Adams & Morsi (1976 ); Gowda, Foro, Babitha & Fuess (2007a ,b ,c ,d ,e ); Gowda, Foro, Nayak & Fuess (2007a ,b ); Nayak & Gowda (2007 ).

Experimental

Crystal data

C₁₄H₁₁ClO₂
M_r = 246.68
Monoclinic, P 2₁ /c
a = 14.6932 (4) Å
b = 11.3269 (3) Å
c = 7.2386 (2) Å
β = 101.050 (3)°
V = 1182.37 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 100 (2) K
0.40 × 0.28 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.887, T_max = 0.976
17127 measured reflections
2407 independent reflections
1889 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.096
S = 1.04
2407 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 1.04 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED; data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek 2003 ) and ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807062137/bt2647sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062137/bt2647Isup2.hkl

checkCIF report

Comment top

In the present work, the structure of 4-methylphenyl 4-chlorobenzoate (4MP4CBA) has been determined, as part of a study of substituent effects on the structures of industrially significant compounds (Gowda, Foro, Babitha & Fuess, 2007a, 2007b; Gowda, Foro, Nayak & Fuess, 2007a, 2007b). The structure of 4MP4CBA (Fig. 1) resembles those of phenyl benzoate (PBA)(Adams & Morsi, 1976), 4-methylphenyl benzoate (4MPBA) (Gowda, Foro, Nayak & Fuess, 2007b), 4-methylphenyl 4-methylbenzoate (4MP4MBA)(Gowda, Foro, Babitha & Fuess, 2007b) and other aryl benzoates (Gowda, Foro, Babitha & Fuess, 2007a; Gowda, Foro, Nayak & Fuess, 2007a). The bond parameters in 4MP4CBA are similar to those in PBA, 4MPBA, 4MP4MBA and other benzoates (Gowda, Foro, Babitha & Fuess, 2007a, 2007b; Gowda, Foro, Nayak & Fuess, 2007a, 2007b). The molecules in the title compound are packed into plane parallel to (-1 0 2) (Fig. 2).

Related literature top

For related literature, see: Adams & Morsi (1976); Gowda, Foro, Babitha & Fuess (2007a,b,c,d,e); Gowda, Foro, Nayak & Fuess (2007a,b); Nayak & Gowda (2007).

Experimental top

The title compound was prepared according to a literature method (Nayak & Gowda, 2007). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Nayak & Gowda, 2007). 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.

Structure description top

For related literature, see: Adams & Morsi (1976); Gowda, Foro, Babitha & Fuess (2007a,b,c,d,e); Gowda, Foro, Nayak & Fuess (2007a,b); Nayak & Gowda (2007).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek 2003) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom labeling. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radius.
	Fig. 2. Molecular packing of the title compound.

4-Methylphenyl 4-chlorobenzoate top

Crystal data top

C₁₄H₁₁ClO₂	F(000) = 512
M_r = 246.68	D_x = 1.386 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 5716 reflections
a = 14.6932 (4) Å	θ = 2.2–26.9°
b = 11.3269 (3) Å	µ = 0.31 mm⁻¹
c = 7.2386 (2) Å	T = 100 K
β = 101.050 (3)°	Prism, colourless
V = 1182.37 (6) Å³	0.40 × 0.28 × 0.08 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2407 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1889 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 8.4012 pixels mm^-1	θ_max = 26.4°, θ_min = 2.3°
Rotation method data acquisition using ω scans.	h = −18→18
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −13→14
T_min = 0.887, T_max = 0.976	l = −9→9
17127 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0437P)² + 0.873P] where P = (F_o² + 2F_c²)/3
2407 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 1.04 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₄H₁₁ClO₂	V = 1182.37 (6) Å³
M_r = 246.68	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.6932 (4) Å	µ = 0.31 mm⁻¹
b = 11.3269 (3) Å	T = 100 K
c = 7.2386 (2) Å	0.40 × 0.28 × 0.08 mm
β = 101.050 (3)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2407 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	1889 reflections with I > 2σ(I)
T_min = 0.887, T_max = 0.976	R_int = 0.023
17127 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.04	Δρ_max = 1.04 e Å⁻³
2407 reflections	Δρ_min = −0.29 e Å⁻³
155 parameters

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	U_iso*/U_eq
Cl1	−0.39495 (3)	0.43951 (5)	0.00266 (7)	0.03131 (16)
O1	0.06211 (8)	0.40950 (10)	0.28512 (17)	0.0203 (3)
O2	0.02463 (9)	0.23571 (11)	0.40524 (18)	0.0264 (3)
C1	−0.27915 (12)	0.40681 (16)	0.0929 (2)	0.0204 (4)
C2	−0.25731 (12)	0.30158 (16)	0.1886 (2)	0.0214 (4)
H2	−0.3045	0.2473	0.2043	0.026*
C3	−0.16463 (12)	0.27738 (15)	0.2611 (2)	0.0193 (4)
H3	−0.1481	0.2058	0.3275	0.023*
C4	−0.09585 (11)	0.35718 (15)	0.2371 (2)	0.0172 (3)
C5	−0.11937 (12)	0.46239 (15)	0.1393 (2)	0.0184 (4)
H5	−0.0723	0.5167	0.1224	0.022*
C6	−0.21182 (12)	0.48738 (15)	0.0668 (2)	0.0196 (4)
H6	−0.2287	0.5588	0.0002	0.024*
C7	0.00171 (12)	0.32497 (15)	0.3186 (2)	0.0188 (4)
C8	0.15790 (11)	0.38716 (16)	0.3334 (2)	0.0185 (4)
C9	0.19650 (12)	0.28504 (15)	0.2769 (2)	0.0197 (4)
H9	0.1583	0.2245	0.2123	0.024*
C10	0.29215 (12)	0.27312 (15)	0.3169 (2)	0.0208 (4)
H10	0.3193	0.2028	0.2806	0.025*
C11	0.34947 (12)	0.36115 (16)	0.4084 (2)	0.0222 (4)
C12	0.30820 (12)	0.46299 (16)	0.4619 (2)	0.0224 (4)
H12	0.3462	0.5244	0.5243	0.027*
C13	0.21257 (12)	0.47634 (15)	0.4254 (2)	0.0199 (4)
H13	0.1851	0.5460	0.4633	0.024*
C14	0.45367 (13)	0.34475 (18)	0.4483 (3)	0.0327 (5)
H14A	0.4683	0.2603	0.4581	0.049*
H14B	0.4805	0.3840	0.5669	0.049*
H14C	0.4797	0.3794	0.3457	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0190 (2)	0.0368 (3)	0.0365 (3)	0.00206 (19)	0.00115 (18)	0.0060 (2)
O1	0.0181 (6)	0.0181 (6)	0.0245 (6)	−0.0002 (5)	0.0033 (5)	0.0019 (5)
O2	0.0240 (7)	0.0247 (7)	0.0303 (7)	0.0022 (5)	0.0044 (5)	0.0110 (6)
C1	0.0170 (8)	0.0249 (9)	0.0192 (9)	0.0012 (7)	0.0032 (7)	−0.0033 (7)
C2	0.0224 (9)	0.0220 (9)	0.0200 (9)	−0.0038 (7)	0.0049 (7)	−0.0003 (7)
C3	0.0254 (9)	0.0158 (8)	0.0168 (8)	−0.0002 (7)	0.0043 (7)	0.0003 (7)
C4	0.0206 (8)	0.0167 (8)	0.0149 (8)	0.0011 (7)	0.0052 (6)	−0.0018 (7)
C5	0.0221 (8)	0.0160 (8)	0.0184 (8)	−0.0012 (7)	0.0070 (7)	−0.0010 (7)
C6	0.0239 (9)	0.0168 (8)	0.0190 (8)	0.0033 (7)	0.0062 (7)	0.0012 (7)
C7	0.0215 (8)	0.0184 (9)	0.0171 (8)	−0.0022 (7)	0.0051 (7)	−0.0016 (7)
C8	0.0183 (8)	0.0209 (9)	0.0167 (8)	0.0008 (7)	0.0047 (7)	0.0041 (7)
C9	0.0252 (9)	0.0173 (9)	0.0166 (8)	−0.0010 (7)	0.0043 (7)	0.0000 (7)
C10	0.0265 (9)	0.0178 (9)	0.0200 (8)	0.0031 (7)	0.0087 (7)	0.0009 (7)
C11	0.0221 (9)	0.0234 (9)	0.0226 (9)	0.0010 (7)	0.0080 (7)	0.0037 (7)
C12	0.0241 (9)	0.0200 (9)	0.0231 (9)	−0.0041 (7)	0.0045 (7)	−0.0005 (7)
C13	0.0239 (9)	0.0166 (8)	0.0205 (9)	0.0013 (7)	0.0074 (7)	−0.0002 (7)
C14	0.0221 (9)	0.0310 (11)	0.0448 (12)	0.0012 (8)	0.0061 (8)	0.0015 (9)

Geometric parameters (Å, º) top

Cl1—C1	1.7414 (17)	C8—C13	1.380 (2)
O1—C7	1.359 (2)	C8—C9	1.384 (2)
O1—C8	1.407 (2)	C9—C10	1.386 (2)
O2—C7	1.203 (2)	C9—H9	0.9500
C1—C2	1.385 (3)	C10—C11	1.389 (3)
C1—C6	1.385 (3)	C10—H10	0.9500
C2—C3	1.390 (2)	C11—C12	1.392 (3)
C2—H2	0.9500	C11—C14	1.514 (2)
C3—C4	1.391 (2)	C12—C13	1.387 (2)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.395 (2)	C13—H13	0.9500
C4—C7	1.487 (2)	C14—H14A	0.9800
C5—C6	1.388 (2)	C14—H14B	0.9800
C5—H5	0.9500	C14—H14C	0.9800
C6—H6	0.9500

C7—O1—C8	119.05 (13)	C13—C8—O1	116.77 (15)
C2—C1—C6	122.14 (16)	C9—C8—O1	121.61 (15)
C2—C1—Cl1	119.12 (14)	C8—C9—C10	118.44 (16)
C6—C1—Cl1	118.74 (14)	C8—C9—H9	120.8
C1—C2—C3	118.36 (16)	C10—C9—H9	120.8
C1—C2—H2	120.8	C9—C10—C11	121.84 (16)
C3—C2—H2	120.8	C9—C10—H10	119.1
C2—C3—C4	120.50 (16)	C11—C10—H10	119.1
C2—C3—H3	119.8	C10—C11—C12	118.09 (16)
C4—C3—H3	119.8	C10—C11—C14	120.10 (16)
C3—C4—C5	120.19 (16)	C12—C11—C14	121.81 (17)
C3—C4—C7	117.33 (15)	C13—C12—C11	121.12 (17)
C5—C4—C7	122.48 (15)	C13—C12—H12	119.4
C6—C5—C4	119.67 (16)	C11—C12—H12	119.4
C6—C5—H5	120.2	C8—C13—C12	119.11 (16)
C4—C5—H5	120.2	C8—C13—H13	120.4
C1—C6—C5	119.14 (16)	C12—C13—H13	120.4
C1—C6—H6	120.4	C11—C14—H14A	109.5
C5—C6—H6	120.4	C11—C14—H14B	109.5
O2—C7—O1	123.92 (15)	H14A—C14—H14B	109.5
O2—C7—C4	124.41 (15)	C11—C14—H14C	109.5
O1—C7—C4	111.66 (14)	H14A—C14—H14C	109.5
C13—C8—C9	121.39 (16)	H14B—C14—H14C	109.5

C6—C1—C2—C3	0.4 (3)	C3—C4—C7—O1	179.72 (14)
Cl1—C1—C2—C3	−179.45 (13)	C5—C4—C7—O1	−0.1 (2)
C1—C2—C3—C4	−0.2 (3)	C7—O1—C8—C13	−134.88 (16)
C2—C3—C4—C5	−0.2 (3)	C7—O1—C8—C9	50.6 (2)
C2—C3—C4—C7	−179.97 (15)	C13—C8—C9—C10	0.8 (3)
C3—C4—C5—C6	0.3 (2)	O1—C8—C9—C10	174.97 (14)
C7—C4—C5—C6	−179.89 (15)	C8—C9—C10—C11	−1.1 (3)
C2—C1—C6—C5	−0.2 (3)	C9—C10—C11—C12	0.6 (3)
Cl1—C1—C6—C5	179.59 (13)	C9—C10—C11—C14	−179.67 (17)
C4—C5—C6—C1	−0.1 (3)	C10—C11—C12—C13	0.2 (3)
C8—O1—C7—O2	7.9 (2)	C14—C11—C12—C13	−179.55 (17)
C8—O1—C7—C4	−172.71 (14)	C9—C8—C13—C12	0.0 (3)
C3—C4—C7—O2	−0.9 (3)	O1—C8—C13—C12	−174.50 (15)
C5—C4—C7—O2	179.27 (17)	C11—C12—C13—C8	−0.5 (3)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁ClO₂
M_r	246.68
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	14.6932 (4), 11.3269 (3), 7.2386 (2)
β (°)	101.050 (3)
V (Å³)	1182.37 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.40 × 0.28 × 0.08

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.887, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	17127, 2407, 1889
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.096, 1.04
No. of reflections	2407
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.04, −0.29

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek 2003) and ORTEP-3 (Farrugia, 1997).

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

References

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