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The structure of the title compound, C13H8Cl2O2, closely resembles those of phenyl benzoate, 3-methyl­phenyl benzoate and 4-methyl­phenyl benzoate, with similar geometric parameters. The dihedral angle between the phenyl and benzoyl rings is 53.77 (5)°, compared to values of 55.7° in phenyl benzoate, 79.61 (6)° in 3-methyl­phenyl benzoate and 60.17 (7)° in 4-methyl­phenyl benzoate.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807039396/bt2472sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807039396/bt2472Isup2.hkl
Contains datablock I

CCDC reference: 660285

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.043
  • wR factor = 0.116
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

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, Foro, Babitha & Fuess, 2007; Gowda, Foro, Nayak & Fuess, 2007), the structure of 3,4-dichlorophenyl benzoate has been determined. The structure (Fig. 1) is similar to that of phenyl benzoate (Adams & Morsi, 1976), 3-methylphenyl benzoate (Gowda, Foro, Babitha & Fuess, 2007) and 4-methylphenyl benzoate (Gowda, Foro, Nayak & Fuess, 2007). The bond parameters in are similar to those in other benzoates.

Related literature top

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

Refinement top

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

Structure description top

In the present work, as part of a study of the substituent effects on the structures of chemically and industrially significant compounds (Gowda, Foro, Babitha & Fuess, 2007; Gowda, Foro, Nayak & Fuess, 2007), the structure of 3,4-dichlorophenyl benzoate has been determined. The structure (Fig. 1) is similar to that of phenyl benzoate (Adams & Morsi, 1976), 3-methylphenyl benzoate (Gowda, Foro, Babitha & Fuess, 2007) and 4-methylphenyl benzoate (Gowda, Foro, Nayak & Fuess, 2007). The bond parameters in are similar to those in other benzoates.

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

Computing details top

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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] 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.
[Figure 2] Fig. 2. Packing diagram of the title compound.
3,4-Dichlorophenyl benzoate top
Crystal data top
C13H8Cl2O2F(000) = 544
Mr = 267.09Dx = 1.504 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 6.1145 (7) Åθ = 3.4–22.4°
b = 13.161 (2) ŵ = 4.84 mm1
c = 14.696 (2) ÅT = 296 K
β = 94.20 (1)°Prism, colourless
V = 1179.5 (3) Å30.28 × 0.20 × 0.18 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
1769 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
Graphite monochromatorθmax = 66.9°, θmin = 4.5°
ω/2θ scansh = 07
Absorption correction: ψ scan
(North et al., 1968)
k = 1512
Tmin = 0.350, Tmax = 0.423l = 1717
4317 measured reflections3 standard reflections every 120 min
2100 independent reflections intensity decay: 1.0%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0717P)2 + 0.1729P]
where P = (Fo2 + 2Fc2)/3
2100 reflections(Δ/σ)max = 0.001
154 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.42 e Å3
Crystal data top
C13H8Cl2O2V = 1179.5 (3) Å3
Mr = 267.09Z = 4
Monoclinic, P21/cCu Kα radiation
a = 6.1145 (7) ŵ = 4.84 mm1
b = 13.161 (2) ÅT = 296 K
c = 14.696 (2) Å0.28 × 0.20 × 0.18 mm
β = 94.20 (1)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
1769 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.037
Tmin = 0.350, Tmax = 0.4233 standard reflections every 120 min
4317 measured reflections intensity decay: 1.0%
2100 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.07Δρmax = 0.26 e Å3
2100 reflectionsΔρmin = 0.42 e Å3
154 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
xyzUiso*/Ueq
C10.3955 (3)0.57105 (15)0.38247 (13)0.0408 (4)
C20.2631 (3)0.49899 (15)0.41736 (13)0.0439 (4)
H20.13840.51820.44570.053*
C30.3165 (3)0.39790 (15)0.40998 (13)0.0428 (4)
C40.5025 (3)0.36930 (15)0.36829 (13)0.0443 (4)
C50.6353 (3)0.44300 (17)0.33486 (14)0.0486 (5)
H50.76170.42410.30760.058*
C60.5829 (3)0.54449 (17)0.34145 (13)0.0466 (5)
H60.67230.59410.31860.056*
C70.1607 (3)0.71002 (15)0.35000 (12)0.0408 (4)
C80.1318 (3)0.82035 (15)0.36432 (12)0.0414 (4)
C90.2958 (4)0.88165 (16)0.40366 (15)0.0535 (5)
H90.42900.85370.42570.064*
C100.2597 (5)0.98542 (18)0.40998 (17)0.0675 (7)
H100.36991.02730.43580.081*
C110.0625 (5)1.02650 (18)0.37843 (17)0.0688 (7)
H110.03921.09610.38330.083*
C120.1004 (4)0.96541 (19)0.33972 (17)0.0650 (6)
H120.23360.99380.31820.078*
C130.0678 (4)0.86248 (17)0.33260 (15)0.0532 (5)
H130.17890.82120.30660.064*
O10.3519 (2)0.67433 (10)0.39223 (10)0.0479 (4)
O20.0353 (2)0.65649 (12)0.30619 (11)0.0571 (4)
Cl10.14815 (11)0.30812 (4)0.45478 (5)0.0679 (2)
Cl20.56926 (11)0.24258 (4)0.35640 (5)0.0687 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0372 (9)0.0385 (9)0.0461 (10)0.0025 (8)0.0009 (8)0.0036 (8)
C20.0391 (10)0.0449 (10)0.0488 (10)0.0015 (8)0.0106 (8)0.0051 (8)
C30.0407 (10)0.0434 (10)0.0448 (10)0.0065 (8)0.0062 (8)0.0001 (8)
C40.0471 (11)0.0409 (10)0.0449 (10)0.0039 (8)0.0020 (8)0.0061 (8)
C50.0392 (10)0.0574 (12)0.0504 (11)0.0017 (9)0.0102 (8)0.0048 (9)
C60.0364 (9)0.0520 (11)0.0518 (11)0.0084 (8)0.0063 (8)0.0027 (9)
C70.0367 (9)0.0432 (10)0.0427 (9)0.0072 (8)0.0045 (8)0.0019 (8)
C80.0425 (10)0.0412 (10)0.0408 (9)0.0034 (8)0.0050 (8)0.0054 (7)
C90.0576 (12)0.0445 (11)0.0565 (12)0.0034 (9)0.0081 (10)0.0004 (9)
C100.0873 (19)0.0463 (12)0.0658 (14)0.0084 (12)0.0167 (13)0.0038 (11)
C110.098 (2)0.0422 (12)0.0651 (14)0.0104 (13)0.0023 (13)0.0015 (10)
C120.0644 (15)0.0580 (14)0.0718 (15)0.0134 (12)0.0003 (12)0.0115 (11)
C130.0455 (11)0.0518 (12)0.0621 (13)0.0019 (9)0.0019 (9)0.0071 (10)
O10.0418 (7)0.0382 (7)0.0624 (8)0.0026 (6)0.0054 (6)0.0041 (6)
O20.0469 (8)0.0497 (8)0.0728 (10)0.0089 (7)0.0076 (7)0.0057 (7)
Cl10.0676 (4)0.0481 (3)0.0911 (5)0.0146 (3)0.0276 (3)0.0038 (3)
Cl20.0754 (4)0.0474 (3)0.0844 (4)0.0121 (3)0.0138 (3)0.0098 (3)
Geometric parameters (Å, º) top
C1—C21.371 (3)C7—O11.366 (2)
C1—C61.378 (3)C7—C81.480 (3)
C1—O11.395 (2)C8—C91.380 (3)
C2—C31.376 (3)C8—C131.390 (3)
C2—H20.9300C9—C101.388 (3)
C3—C41.383 (3)C9—H90.9300
C3—Cl11.7288 (19)C10—C111.371 (4)
C4—C51.379 (3)C10—H100.9300
C4—Cl21.729 (2)C11—C121.371 (4)
C5—C61.379 (3)C11—H110.9300
C5—H50.9300C12—C131.374 (3)
C6—H60.9300C12—H120.9300
C7—O21.194 (2)C13—H130.9300
C2—C1—C6121.40 (19)O1—C7—C8112.32 (15)
C2—C1—O1120.86 (17)C9—C8—C13120.0 (2)
C6—C1—O1117.63 (17)C9—C8—C7122.87 (19)
C1—C2—C3119.29 (18)C13—C8—C7117.05 (18)
C1—C2—H2120.4C8—C9—C10119.3 (2)
C3—C2—H2120.4C8—C9—H9120.4
C2—C3—C4120.38 (18)C10—C9—H9120.4
C2—C3—Cl1118.64 (15)C11—C10—C9120.4 (2)
C4—C3—Cl1120.97 (16)C11—C10—H10119.8
C5—C4—C3119.43 (19)C9—C10—H10119.8
C5—C4—Cl2119.55 (16)C10—C11—C12120.2 (2)
C3—C4—Cl2121.01 (16)C10—C11—H11119.9
C4—C5—C6120.70 (19)C12—C11—H11119.9
C4—C5—H5119.7C11—C12—C13120.3 (2)
C6—C5—H5119.7C11—C12—H12119.8
C1—C6—C5118.80 (19)C13—C12—H12119.8
C1—C6—H6120.6C12—C13—C8119.8 (2)
C5—C6—H6120.6C12—C13—H13120.1
O2—C7—O1122.42 (18)C8—C13—H13120.1
O2—C7—C8125.26 (18)C7—O1—C1116.90 (14)
C6—C1—C2—C31.0 (3)O2—C7—C8—C137.4 (3)
O1—C1—C2—C3177.17 (17)O1—C7—C8—C13173.30 (17)
C1—C2—C3—C40.4 (3)C13—C8—C9—C100.8 (3)
C1—C2—C3—Cl1179.74 (14)C7—C8—C9—C10176.4 (2)
C2—C3—C4—C50.6 (3)C8—C9—C10—C110.7 (4)
Cl1—C3—C4—C5178.77 (15)C9—C10—C11—C120.5 (4)
C2—C3—C4—Cl2178.71 (15)C10—C11—C12—C130.3 (4)
Cl1—C3—C4—Cl21.9 (2)C11—C12—C13—C80.4 (4)
C3—C4—C5—C60.9 (3)C9—C8—C13—C120.7 (3)
Cl2—C4—C5—C6178.39 (16)C7—C8—C13—C12176.7 (2)
C2—C1—C6—C50.7 (3)O2—C7—O1—C10.3 (3)
O1—C1—C6—C5176.96 (17)C8—C7—O1—C1179.62 (16)
C4—C5—C6—C10.3 (3)C2—C1—O1—C764.2 (2)
O2—C7—C8—C9169.9 (2)C6—C1—O1—C7119.56 (19)
O1—C7—C8—C99.4 (3)

Experimental details

Crystal data
Chemical formulaC13H8Cl2O2
Mr267.09
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)6.1145 (7), 13.161 (2), 14.696 (2)
β (°) 94.20 (1)
V3)1179.5 (3)
Z4
Radiation typeCu Kα
µ (mm1)4.84
Crystal size (mm)0.28 × 0.20 × 0.18
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.350, 0.423
No. of measured, independent and
observed [I > 2σ(I)] reflections
4317, 2100, 1769
Rint0.037
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.116, 1.07
No. of reflections2100
No. of parameters154
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.42

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), CAD-4-PC, REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.

 

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