2,6-Dichloro­phenyl benzoate

The structure of the title compound, C₁₃H₈Cl₂O₂, is similar to those of phenyl benzoate, 3,4-dichloro­phenyl benzoate and other aryl benzoates, with somewhat different bond parameters. The dihedral angle between the two aromatic rings is 75.75 (10)°.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.049
• wR factor = 0.151
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C5     -   C6      ..       6.19 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C6
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 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; Gowda et al., 2007), the structure of 2,6-dichlorophenyl benzoate (26DCPBA) has been determined. The structure of 26DCPBA (Fig. 1) resembles those of phenyl benzoate (PBA) (Adams & Morsi, 1976), 3,4-dichlorophenyl benzoate (34DCPBA) (Gowda et al., 2007b) and other aryl benzoates (Gowda et al., 2007a; Gowda et al., 2007). The bond parameters in 26DCPBA are similar to those in PBA, 34DCPBA and other aryl benzoates. The molecules in 26DCPBA are packed into column like structure with the benzoyl ring in the direction of b axis, while the dichlorophenyl ring being nearly orthogonal to the former(Fig. 2).

Related literature

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

S2. Experimental

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.

S3. Refinement

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

Computing details

Data collection: CAD-4-PC Software (Enraf–Nonius, 1996); cell refinement: CAD-4-PC Software; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures

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

2,6-Dichlorophenyl benzoate

Crystal data

C13H8Cl2O2	F(000) = 544
Mr = 267.09	Dx = 1.445 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.500 (2) Å	θ = 8.0–19.6°
b = 7.9800 (9) Å	µ = 4.65 mm^−1
c = 15.007 (2) Å	T = 299 K
β = 102.55 (1)°	Prism, colourless
V = 1227.4 (3) Å^3	0.55 × 0.35 × 0.20 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	1553 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 67.0°, θmin = 4.3°
ω/2θ scans	h = −12→1
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
Tmin = 0.200, Tmax = 0.406	l = −17→17
2541 measured reflections	3 standard reflections every 120 min
2185 independent reflections	intensity decay: 1.5%

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) = 0.151	w = 1/[σ^2(Fo^2) + (0.0891P)^2 + 0.1792P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.002
2185 reflections	Δρmax = 0.29 e Å^−3
155 parameters	Δρmin = −0.40 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0197 (15)

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	0.1122 (3)	0.4256 (3)	0.36182 (17)	0.0603 (7)
C2	0.0090 (3)	0.3476 (3)	0.38834 (18)	0.0630 (7)
C3	−0.0996 (3)	0.4377 (4)	0.3971 (2)	0.0719 (8)
H3	−0.1680	0.3846	0.4159	0.086*
C4	−0.1064 (4)	0.6032 (5)	0.3782 (2)	0.0788 (9)
H4	−0.1804	0.6631	0.3834	0.095*
C5	−0.0059 (4)	0.6843 (4)	0.3513 (2)	0.0814 (10)
H5	−0.0117	0.7985	0.3385	0.098*
C6	0.1044 (3)	0.5955 (4)	0.34339 (18)	0.0659 (7)
C7	0.3223 (3)	0.3196 (3)	0.42049 (19)	0.0615 (7)
C8	0.4239 (3)	0.2098 (3)	0.3977 (2)	0.0620 (7)
C9	0.5440 (3)	0.2070 (4)	0.4583 (3)	0.0821 (9)
H9	0.5592	0.2741	0.5101	0.098*
C10	0.6410 (4)	0.1028 (6)	0.4405 (4)	0.1016 (13)
H10	0.7217	0.0989	0.4810	0.122*
C11	0.6184 (4)	0.0059 (6)	0.3637 (4)	0.1099 (15)
H11	0.6843	−0.0628	0.3519	0.132*
C12	0.4996 (5)	0.0090 (5)	0.3041 (3)	0.1052 (13)
H12	0.4849	−0.0577	0.2520	0.126*
C13	0.4015 (4)	0.1111 (4)	0.3212 (2)	0.0805 (9)
H13	0.3205	0.1128	0.2809	0.097*
O1	0.21813 (19)	0.3328 (3)	0.34784 (13)	0.0707 (6)
O2	0.3255 (2)	0.3910 (3)	0.49034 (15)	0.0826 (7)
Cl1	0.01973 (10)	0.13767 (9)	0.41347 (6)	0.0910 (4)
Cl2	0.23311 (11)	0.69468 (14)	0.31154 (7)	0.1058 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0727 (17)	0.0557 (15)	0.0483 (13)	0.0110 (13)	0.0036 (12)	−0.0060 (11)
C2	0.0748 (18)	0.0537 (15)	0.0561 (14)	0.0037 (13)	0.0049 (13)	−0.0045 (12)
C3	0.0705 (18)	0.0787 (19)	0.0643 (16)	0.0103 (16)	0.0096 (14)	−0.0024 (15)
C4	0.087 (2)	0.081 (2)	0.0630 (17)	0.0311 (18)	0.0043 (16)	−0.0047 (15)
C5	0.122 (3)	0.0526 (16)	0.0604 (17)	0.0200 (18)	−0.0015 (18)	0.0003 (13)
C6	0.0821 (19)	0.0575 (16)	0.0537 (15)	0.0021 (14)	0.0053 (13)	0.0015 (12)
C7	0.0679 (17)	0.0553 (14)	0.0600 (16)	0.0013 (12)	0.0109 (13)	0.0013 (12)
C8	0.0642 (16)	0.0517 (14)	0.0720 (17)	0.0043 (12)	0.0187 (14)	0.0128 (12)
C9	0.071 (2)	0.076 (2)	0.097 (2)	0.0011 (16)	0.0145 (17)	0.0142 (18)
C10	0.069 (2)	0.094 (3)	0.146 (4)	0.016 (2)	0.031 (2)	0.035 (3)
C11	0.093 (3)	0.093 (3)	0.159 (4)	0.032 (2)	0.061 (3)	0.030 (3)
C12	0.119 (3)	0.088 (3)	0.120 (3)	0.027 (2)	0.051 (3)	−0.006 (2)
C13	0.085 (2)	0.0741 (19)	0.086 (2)	0.0123 (17)	0.0276 (18)	−0.0015 (17)
O1	0.0699 (12)	0.0779 (13)	0.0614 (11)	0.0193 (10)	0.0079 (9)	−0.0109 (9)
O2	0.0791 (14)	0.0949 (16)	0.0688 (12)	0.0136 (12)	0.0053 (10)	−0.0163 (12)
Cl1	0.1106 (7)	0.0539 (4)	0.1032 (7)	−0.0007 (4)	0.0117 (5)	0.0051 (4)
Cl2	0.1166 (8)	0.1045 (8)	0.0927 (7)	−0.0266 (6)	0.0150 (5)	0.0248 (5)

Geometric parameters (Å, º)

C1—C2	1.380 (4)	C7—O1	1.370 (3)
C1—C6	1.382 (4)	C7—C8	1.478 (4)
C1—O1	1.390 (3)	C8—C13	1.370 (4)
C2—C3	1.378 (4)	C8—C9	1.385 (5)
C2—Cl1	1.715 (3)	C9—C10	1.384 (5)
C3—C4	1.349 (5)	C9—H9	0.9300
C3—H3	0.9300	C10—C11	1.365 (6)
C4—C5	1.371 (5)	C10—H10	0.9300
C4—H4	0.9300	C11—C12	1.369 (7)
C5—C6	1.384 (5)	C11—H11	0.9300
C5—H5	0.9300	C12—C13	1.380 (5)
C6—Cl2	1.721 (3)	C12—H12	0.9300
C7—O2	1.187 (3)	C13—H13	0.9300
C2—C1—C6	118.9 (3)	O1—C7—C8	110.7 (2)
C2—C1—O1	120.5 (3)	C13—C8—C9	120.5 (3)
C6—C1—O1	120.5 (3)	C13—C8—C7	122.3 (3)
C3—C2—C1	120.6 (3)	C9—C8—C7	117.2 (3)
C3—C2—Cl1	120.3 (3)	C10—C9—C8	119.1 (4)
C1—C2—Cl1	119.1 (2)	C10—C9—H9	120.5
C4—C3—C2	119.9 (3)	C8—C9—H9	120.5
C4—C3—H3	120.1	C11—C10—C9	120.2 (4)
C2—C3—H3	120.1	C11—C10—H10	119.9
C3—C4—C5	120.9 (3)	C9—C10—H10	119.9
C3—C4—H4	119.5	C10—C11—C12	120.5 (4)
C5—C4—H4	119.5	C10—C11—H11	119.7
C4—C5—C6	119.7 (3)	C12—C11—H11	119.7
C4—C5—H5	120.2	C11—C12—C13	120.0 (4)
C6—C5—H5	120.2	C11—C12—H12	120.0
C1—C6—C5	120.0 (3)	C13—C12—H12	120.0
C1—C6—Cl2	119.4 (3)	C8—C13—C12	119.7 (4)
C5—C6—Cl2	120.7 (3)	C8—C13—H13	120.1
O2—C7—O1	122.1 (3)	C12—C13—H13	120.1
O2—C7—C8	127.3 (3)	C7—O1—C1	116.6 (2)
C6—C1—C2—C3	−0.5 (4)	O1—C7—C8—C13	−12.2 (4)
O1—C1—C2—C3	−176.2 (2)	O2—C7—C8—C9	−10.0 (4)
C6—C1—C2—Cl1	−178.7 (2)	O1—C7—C8—C9	169.3 (3)
O1—C1—C2—Cl1	5.7 (3)	C13—C8—C9—C10	−0.1 (5)
C1—C2—C3—C4	1.1 (4)	C7—C8—C9—C10	178.5 (3)
Cl1—C2—C3—C4	179.2 (2)	C8—C9—C10—C11	0.7 (5)
C2—C3—C4—C5	−0.8 (5)	C9—C10—C11—C12	−0.7 (6)
C3—C4—C5—C6	0.0 (5)	C10—C11—C12—C13	0.2 (7)
C2—C1—C6—C5	−0.2 (4)	C9—C8—C13—C12	−0.5 (5)
O1—C1—C6—C5	175.4 (2)	C7—C8—C13—C12	−179.0 (3)
C2—C1—C6—Cl2	179.26 (19)	C11—C12—C13—C8	0.4 (6)
O1—C1—C6—Cl2	−5.1 (3)	O2—C7—O1—C1	−4.0 (4)
C4—C5—C6—C1	0.5 (4)	C8—C7—O1—C1	176.6 (2)
C4—C5—C6—Cl2	−179.0 (2)	C2—C1—O1—C7	−93.7 (3)
O2—C7—C8—C13	168.5 (3)	C6—C1—O1—C7	90.7 (3)