2,6-Dichloro­phenyl 4-methyl­benzoate

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.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.050
• wR factor = 0.169
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2    ..  O2      ..       3.12 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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

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

S3. Refinement

The H atoms were positioned with idealized geometry using a riding model (C—H = 0.93–0.96 Å) with U_iso = 1.2 U_eq of the parent atom.

Computing details

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

	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

Crystal data

C14H10Cl2O2	F(000) = 576
Mr = 281.12	Dx = 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) Å^3	0.60 × 0.35 × 0.30 mm
Z = 4

Data collection

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

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)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.168	w = 1/[σ^2(Fo^2) + (0.1211P)^2 + 0.3061P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.011
2366 reflections	Δρmax = 0.36 e Å^−3
165 parameters	Δρmin = −0.43 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0170 (18)

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
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 (Ų)

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

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)