2,6-Dichloro­phenyl 4-methyl­benzoate

Gowda, B.T.; Foro, S.; Babitha, K.S.; Fuess, H.

doi:10.1107/S1600536808009616

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o843

doi:10.1107/S1600536808009616

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2,6-Dichlorophenyl 4-methylbenzoate

B. Thimme Gowda,^a ^* Sabine Foro,^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 26 March 2008; accepted 7 April 2008; online 16 April 2008)

The structure of the title compound (26DCP4MeBA), C₁₄H₁₀Cl₂O₂, resembles those of phenyl benzoate (PBA), 2,6-dichlorophenyl benzoate (26DCPBA), 2,4-dichlorophenyl 4-methylbenzoate (24DCP4MeBA) and other aryl benzoates, with similar bond parameters. The dihedral angle between the benzene and benzoyl rings in 26DCP4MeBA is 77.97 (9)°, compared with values of 55.7 (PBA), 75.75 (10) (26DCPBA) and 48.13 (5)° (24DCP4MeBA). The molecules in the title compound are packed into zigzag chains in the bc plane.

Related literature

For related literature, see: Adams & Morsi (1976 ); Gowda et al. (2007a ,b ); Nayak & Gowda (2008 ).

Experimental

Crystal data

C₁₄H₁₀Cl₂O₂
M_r = 281.12
Monoclinic, P 2₁ /n
a = 9.5688 (8) Å
b = 11.1370 (9) Å
c = 13.1947 (9) Å
β = 108.898 (7)°
V = 1330.33 (18) Å³
Z = 4
Cu Kα radiation
μ = 4.32 mm⁻¹
T = 299 (2) K
0.60 × 0.35 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.202, T_max = 0.273
3035 measured reflections
2366 independent reflections
2025 reflections with I > 2σ(I)
R_int = 0.040
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.168
S = 1.01
2366 reflections
165 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ); cell refinement: CAD-4-PC; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808009616/om2223sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808009616/om2223Isup2.hkl

checkCIF report

Comment top

In the present work, as part of a study of the substituent effects on the structures of chemically and industrially significant compounds (Gowda et al., 2007a,b), the structure of 2,6-dichlorophenyl 4-methylbenzoate (26DCP4MeBA) has been determined. The structure of 26DCP4MeBA (Fig. 1) resembles those of phenyl benzoate (PBA) (Adams & Morsi, 1976), 2,6-dichlorophenyl benzoate (26DCPBA) (Gowda et al., 2007a), 2,4-dichlorophenyl 4-methyl benzoate (24DCP4MeBA) (Gowda et al., 2007b) and other aryl benzoates. The bond parameters in 26DCP4MeBA are similar to those in PBA, 26DCPBA, 24DCP4MeBA and other benzoates. The dihedral angle between the benzene and benzoyl rings in 26DCP4MeBA is 77.97 (9)°, compared to the values of 55.7° (PBA)(Adams & Morsi, 1976), 75.75 (10)° (26DCPBA)(Gowda et al., 2007a) and 48.13 (5)° (24DCP4MeBA)(Gowda et al., 2007b). The molecules in 26DCP4MeBA are packed into a zigzag structure with the dichlorophenyl ring being nearly orthogonal to the benzoyl ring (Fig. 2).

Related literature top

For related literature, see: Adams & Morsi (1976); Gowda et al. (2007a,b); Nayak & Gowda (2008).

Experimental top

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.

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC (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 top

	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 a.
	Fig. 3. A view of the title molecule and unit cell

2,6-Dichlorophenyl 4-methylbenzoate top

Crystal data top

C₁₄H₁₀Cl₂O₂	F(000) = 576
M_r = 281.12	D_x = 1.404 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 9.5688 (8) Å	θ = 5.3–18.7°
b = 11.1370 (9) Å	µ = 4.32 mm⁻¹
c = 13.1947 (9) Å	T = 299 K
β = 108.898 (7)°	Rod, colourless
V = 1330.33 (18) Å³	0.60 × 0.35 × 0.30 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	2025 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.040
Graphite monochromator	θ_max = 67.0°, θ_min = 5.0°
ω/2θ scans	h = −11→2
Absorption correction: ψ scan (North et al., 1968)	k = −13→0
T_min = 0.202, T_max = 0.273	l = −15→15
3035 measured reflections	3 standard reflections every 120 min
2366 independent reflections	intensity decay: none

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)] = 0.049	H-atom parameters constrained
wR(F²) = 0.168	w = 1/[σ²(F_o²) + (0.1211P)² + 0.3061P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.011
2366 reflections	Δρ_max = 0.36 e Å⁻³
165 parameters	Δρ_min = −0.43 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: 0.0170 (18)

Crystal data top

C₁₄H₁₀Cl₂O₂	V = 1330.33 (18) Å³
M_r = 281.12	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 9.5688 (8) Å	µ = 4.32 mm⁻¹
b = 11.1370 (9) Å	T = 299 K
c = 13.1947 (9) Å	0.60 × 0.35 × 0.30 mm
β = 108.898 (7)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2025 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.040
T_min = 0.202, T_max = 0.273	3 standard reflections every 120 min
3035 measured reflections	intensity decay: none
2366 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.168	H-atom parameters constrained
S = 1.01	Δρ_max = 0.36 e Å⁻³
2366 reflections	Δρ_min = −0.43 e Å⁻³
165 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
C1	0.1987 (2)	0.6943 (2)	0.02446 (17)	0.0490 (5)
C2	0.1627 (3)	0.5987 (2)	−0.0454 (2)	0.0568 (6)
C3	0.0175 (3)	0.5780 (3)	−0.1077 (2)	0.0683 (7)
H3	−0.0065	0.5127	−0.1541	0.082*
C4	−0.0902 (3)	0.6551 (3)	−0.0999 (2)	0.0705 (7)
H4	−0.1879	0.6418	−0.1415	0.085*
C5	−0.0563 (3)	0.7510 (3)	−0.0320 (2)	0.0679 (7)
H5	−0.1304	0.8030	−0.0280	0.082*
C6	0.0887 (3)	0.7707 (2)	0.03086 (19)	0.0547 (6)
C7	0.4023 (2)	0.6546 (2)	0.17553 (18)	0.0499 (5)
C8	0.5626 (2)	0.6726 (2)	0.22269 (17)	0.0484 (5)
C9	0.6386 (3)	0.7563 (2)	0.1830 (2)	0.0636 (7)
H9	0.5881	0.8063	0.1266	0.076*
C10	0.7903 (3)	0.7648 (3)	0.2280 (3)	0.0744 (8)
H10	0.8409	0.8210	0.2009	0.089*
C11	0.8687 (3)	0.6923 (3)	0.3118 (2)	0.0693 (8)
C12	0.7918 (3)	0.6113 (3)	0.3517 (2)	0.0681 (7)
H12	0.8426	0.5620	0.4086	0.082*
C13	0.6393 (3)	0.6016 (2)	0.3082 (2)	0.0574 (6)
H13	0.5887	0.5471	0.3369	0.069*
C14	1.0350 (3)	0.7024 (4)	0.3581 (3)	0.1081 (14)
H14A	1.0606	0.7552	0.4189	0.130*
H14B	1.0733	0.7342	0.3047	0.130*
H14C	1.0766	0.6245	0.3799	0.130*
O1	0.34465 (16)	0.71769 (15)	0.08263 (13)	0.0551 (5)
O2	0.32703 (19)	0.59229 (19)	0.21108 (15)	0.0692 (6)
Cl1	0.30058 (9)	0.50474 (7)	−0.05432 (7)	0.0849 (4)
Cl2	0.13347 (8)	0.89253 (7)	0.11604 (6)	0.0796 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0404 (11)	0.0544 (12)	0.0506 (12)	0.0032 (9)	0.0127 (9)	0.0059 (9)
C2	0.0570 (14)	0.0574 (14)	0.0578 (13)	0.0078 (10)	0.0210 (11)	0.0025 (10)
C3	0.0700 (16)	0.0723 (17)	0.0568 (14)	−0.0073 (13)	0.0124 (12)	−0.0048 (12)
C4	0.0492 (13)	0.093 (2)	0.0597 (15)	−0.0064 (13)	0.0040 (11)	0.0035 (14)
C5	0.0443 (12)	0.091 (2)	0.0654 (15)	0.0142 (12)	0.0139 (11)	0.0084 (14)
C6	0.0488 (12)	0.0627 (14)	0.0522 (12)	0.0091 (10)	0.0157 (10)	0.0002 (10)
C7	0.0464 (12)	0.0493 (12)	0.0528 (12)	−0.0002 (9)	0.0143 (9)	0.0007 (9)
C8	0.0424 (11)	0.0485 (12)	0.0538 (12)	−0.0010 (9)	0.0148 (9)	−0.0070 (9)
C9	0.0577 (14)	0.0586 (14)	0.0741 (16)	−0.0067 (11)	0.0206 (12)	0.0040 (12)
C10	0.0577 (15)	0.0775 (19)	0.090 (2)	−0.0224 (13)	0.0267 (14)	−0.0050 (15)
C11	0.0432 (13)	0.091 (2)	0.0695 (16)	−0.0092 (12)	0.0131 (11)	−0.0208 (14)
C12	0.0478 (13)	0.0830 (18)	0.0635 (15)	0.0035 (12)	0.0042 (11)	−0.0020 (13)
C13	0.0479 (13)	0.0621 (14)	0.0597 (14)	−0.0038 (10)	0.0139 (10)	−0.0018 (10)
C14	0.0438 (15)	0.161 (4)	0.110 (3)	−0.0203 (19)	0.0125 (16)	−0.025 (3)
O1	0.0408 (8)	0.0593 (10)	0.0611 (10)	0.0006 (6)	0.0109 (7)	0.0097 (7)
O2	0.0502 (9)	0.0845 (13)	0.0681 (11)	−0.0149 (8)	0.0125 (8)	0.0170 (9)
Cl1	0.0880 (6)	0.0766 (5)	0.0967 (6)	0.0244 (4)	0.0389 (5)	−0.0084 (4)
Cl2	0.0782 (5)	0.0754 (5)	0.0764 (5)	0.0184 (3)	0.0128 (4)	−0.0178 (3)

Geometric parameters (Å, º) top

C1—C6	1.377 (3)	C8—C13	1.379 (3)
C1—C2	1.377 (3)	C8—C9	1.385 (3)
C1—O1	1.383 (3)	C9—C10	1.382 (4)
C2—C3	1.386 (4)	C9—H9	0.9300
C2—Cl1	1.718 (2)	C10—C11	1.379 (4)
C3—C4	1.371 (4)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.372 (4)
C4—C5	1.364 (4)	C11—C14	1.513 (4)
C4—H4	0.9300	C12—C13	1.389 (4)
C5—C6	1.384 (4)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—Cl2	1.725 (3)	C14—H14A	0.9600
C7—O2	1.199 (3)	C14—H14B	0.9600
C7—O1	1.365 (3)	C14—H14C	0.9600
C7—C8	1.470 (3)

C6—C1—C2	119.2 (2)	C9—C8—C7	122.4 (2)
C6—C1—O1	120.3 (2)	C10—C9—C8	119.4 (3)
C2—C1—O1	120.4 (2)	C10—C9—H9	120.3
C1—C2—C3	120.8 (2)	C8—C9—H9	120.3
C1—C2—Cl1	119.07 (19)	C11—C10—C9	121.8 (3)
C3—C2—Cl1	120.2 (2)	C11—C10—H10	119.1
C4—C3—C2	119.0 (3)	C9—C10—H10	119.1
C4—C3—H3	120.5	C12—C11—C10	118.2 (2)
C2—C3—H3	120.5	C12—C11—C14	121.3 (3)
C5—C4—C3	121.0 (2)	C10—C11—C14	120.5 (3)
C5—C4—H4	119.5	C11—C12—C13	121.0 (3)
C3—C4—H4	119.5	C11—C12—H12	119.5
C4—C5—C6	119.7 (2)	C13—C12—H12	119.5
C4—C5—H5	120.1	C8—C13—C12	120.2 (2)
C6—C5—H5	120.1	C8—C13—H13	119.9
C1—C6—C5	120.2 (2)	C12—C13—H13	119.9
C1—C6—Cl2	119.48 (19)	C11—C14—H14A	109.5
C5—C6—Cl2	120.26 (19)	C11—C14—H14B	109.5
O2—C7—O1	122.0 (2)	H14A—C14—H14B	109.5
O2—C7—C8	126.1 (2)	C11—C14—H14C	109.5
O1—C7—C8	111.85 (18)	H14A—C14—H14C	109.5
C13—C8—C9	119.3 (2)	H14B—C14—H14C	109.5
C13—C8—C7	118.3 (2)	C7—O1—C1	116.30 (17)

C6—C1—C2—C3	−0.9 (4)	O2—C7—C8—C9	−172.7 (3)
O1—C1—C2—C3	−177.0 (2)	O1—C7—C8—C9	7.8 (3)
C6—C1—C2—Cl1	179.23 (18)	C13—C8—C9—C10	1.7 (4)
O1—C1—C2—Cl1	3.2 (3)	C7—C8—C9—C10	−177.0 (2)
C1—C2—C3—C4	0.8 (4)	C8—C9—C10—C11	−0.2 (5)
Cl1—C2—C3—C4	−179.3 (2)	C9—C10—C11—C12	−1.0 (5)
C2—C3—C4—C5	−0.1 (4)	C9—C10—C11—C14	179.0 (3)
C3—C4—C5—C6	−0.6 (4)	C10—C11—C12—C13	0.5 (4)
C2—C1—C6—C5	0.2 (4)	C14—C11—C12—C13	−179.4 (3)
O1—C1—C6—C5	176.3 (2)	C9—C8—C13—C12	−2.2 (4)
C2—C1—C6—Cl2	−178.59 (18)	C7—C8—C13—C12	176.6 (2)
O1—C1—C6—Cl2	−2.5 (3)	C11—C12—C13—C8	1.0 (4)
C4—C5—C6—C1	0.5 (4)	O2—C7—O1—C1	−8.0 (3)
C4—C5—C6—Cl2	179.3 (2)	C8—C7—O1—C1	171.58 (18)
O2—C7—C8—C13	8.5 (4)	C6—C1—O1—C7	100.0 (3)
O1—C7—C8—C13	−171.0 (2)	C2—C1—O1—C7	−84.0 (3)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀Cl₂O₂
M_r	281.12
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	299
a, b, c (Å)	9.5688 (8), 11.1370 (9), 13.1947 (9)
β (°)	108.898 (7)
V (Å³)	1330.33 (18)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	4.32
Crystal size (mm)	0.60 × 0.35 × 0.30

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.202, 0.273
No. of measured, independent and observed [I > 2σ(I)] reflections	3035, 2366, 2025
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.168, 1.01
No. of reflections	2366
No. of parameters	165
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.43

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Acknowledgements

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

References

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