2,6-Dichloro-phenyl 4-methyl-benzoate.

The structure of the title compound (26DCP4MeBA), C(14)H(10)Cl(2)O(2), resembles those of phenyl benzoate (PBA), 2,6-dichloro-phenyl benzoate (26DCPBA), 2,4-dichloro-phenyl 4-methyl-benzoate (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 mol-ecules 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 = 281.12

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.168

S = 1.01

2366 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Enhanced figure: interactive version of Fig. 3

C14H10Cl2O2	F000 = 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 = 5.3–18.7º
b = 11.1370 (9) Å	µ = 4.32 mm−1
c = 13.1947 (9) Å	T = 299 (2) K
β = 108.898 (7)º	Rod, colourless
V = 1330.33 (18) Å3	0.60 × 0.35 × 0.30 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.040
Radiation source: fine-focus sealed tube	θmax = 67.0º
Monochromator: graphite	θmin = 5.0º
T = 299(2) K	h = −11→2
ω/2θ scans	k = −13→0
Absorption correction: ψ scan(North et al., 1968)	l = −15→15
Tmin = 0.202, Tmax = 0.273	3 standard reflections
3035 measured reflections	every 120 min
2366 independent reflections	intensity decay: none
2025 reflections with I > 2σ(I)

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049	w = 1/[σ2(Fo2) + (0.1211P)2 + 0.3061P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.168	(Δ/σ)max = 0.011
S = 1.01	Δρmax = 0.36 e Å−3
2366 reflections	Δρmin = −0.43 e Å−3
165 parameters	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)
Secondary atom site location: difference Fourier map

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.

	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)

	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)

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)