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The structure of the title compound (24DCP4MeBA), C14H10Cl2O2, resembles that of phenyl benzoate (PBA), 4-methyl­phenyl benzoate (4MePBA) and 4-methyl­phenyl 4-methyl­benzoate (4MeP4MeBA), with similar bond parameters. The dihedral angle between the benzene and benzoyl rings in 24DCP4MeBA is 48.13 (5)°, compared with values in the other compounds of 55.7 (PBA), 60.17 (7) (4MePBA) and 63.57 (5)° (4MeP4MeBA). The mol­ecules of 24DCP4MeBA are packed into column-like infinite chains in the direction of the a axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041050/wn2195sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041050/wn2195Isup2.hkl
Contains datablock I

CCDC reference: 660340

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.044
  • wR factor = 0.130
  • Data-to-parameter ratio = 13.7

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 substituent effects on the crystal structures of aromatic esters (Gowda et al., 2007a,b,c; Gowda et al., 2007), the structure of 2,4-dichlorophenyl 4-methyl benzoate (24DCP4MeBA) has been determined. The structure of 24DCP4MeBA (Fig. 1) is similar to those of phenyl benzoate (PBA) (Adams & Morsi, 1976), 4-methylphenyl benzoate (4MePBA) (Gowda et al., 2007) and 4-methylphenyl 4-methylbenzoate (4MeP4MeBA) (Gowda et al., 2007c). The bond parameters in 24DCP4MeBA are similar to those in PBA, 4MePBA, 4MeP4MeBA and other aryl benzoates (Adams & Morsi, 1976; Gowda et al., 2007a,b,c; Gowda et al., 2007). The dihedral angle between the benzene and benzoyl rings in 24DCP4MeBA is 48.13 (5)°, compared to the values of 55.7° (PBA), 60.17 (7)° (4MePBA) and 63.57 (5)° (4MeP4MeBA). The molecules in 24DCP4MeBA are packed into column-like infinite chains in the direction of the a axis·(Fig. 2).

Related literature top

For related literature, see: Adams & Morsi (1976); Gowda et al. (2007, 2007a,b,c); 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 and refined using a riding model (C—H = 0.93–0.96 Å), with Uiso(H) = 1.2Ueq(parent atom).

Structure description top

In the present work, as part of a study of substituent effects on the crystal structures of aromatic esters (Gowda et al., 2007a,b,c; Gowda et al., 2007), the structure of 2,4-dichlorophenyl 4-methyl benzoate (24DCP4MeBA) has been determined. The structure of 24DCP4MeBA (Fig. 1) is similar to those of phenyl benzoate (PBA) (Adams & Morsi, 1976), 4-methylphenyl benzoate (4MePBA) (Gowda et al., 2007) and 4-methylphenyl 4-methylbenzoate (4MeP4MeBA) (Gowda et al., 2007c). The bond parameters in 24DCP4MeBA are similar to those in PBA, 4MePBA, 4MeP4MeBA and other aryl benzoates (Adams & Morsi, 1976; Gowda et al., 2007a,b,c; Gowda et al., 2007). The dihedral angle between the benzene and benzoyl rings in 24DCP4MeBA is 48.13 (5)°, compared to the values of 55.7° (PBA), 60.17 (7)° (4MePBA) and 63.57 (5)° (4MeP4MeBA). The molecules in 24DCP4MeBA are packed into column-like infinite chains in the direction of the a axis·(Fig. 2).

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

Computing details top

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 top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radius.
[Figure 2] Fig. 2. Molecular packing in the title compound.
2,4-Dichlorophenyl 4-methylbenzoate top
Crystal data top
C14H10Cl2O2F(000) = 576
Mr = 281.12Dx = 1.475 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 11.854 (1) Åθ = 5.7–23.9°
b = 7.2039 (9) ŵ = 4.53 mm1
c = 15.653 (2) ÅT = 299 K
β = 108.670 (9)°Plate, colourless
V = 1266.3 (3) Å30.55 × 0.53 × 0.18 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
2027 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
Graphite monochromatorθmax = 66.9°, θmin = 4.1°
ω/2θ scansh = 1411
Absorption correction: ψ scan
(North et al., 1968)
k = 80
Tmin = 0.159, Tmax = 0.443l = 1818
4377 measured reflections3 standard reflections every 120 min
2265 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.130 w = 1/[σ2(Fo2) + (0.0785P)2 + 0.3594P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.044
2265 reflectionsΔρmax = 0.40 e Å3
165 parametersΔρmin = 0.41 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0072 (8)
Crystal data top
C14H10Cl2O2V = 1266.3 (3) Å3
Mr = 281.12Z = 4
Monoclinic, P21/nCu Kα radiation
a = 11.854 (1) ŵ = 4.53 mm1
b = 7.2039 (9) ÅT = 299 K
c = 15.653 (2) Å0.55 × 0.53 × 0.18 mm
β = 108.670 (9)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
2027 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.034
Tmin = 0.159, Tmax = 0.4433 standard reflections every 120 min
4377 measured reflections intensity decay: none
2265 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.130H-atom parameters constrained
S = 1.05Δρmax = 0.40 e Å3
2265 reflectionsΔρmin = 0.41 e Å3
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
xyzUiso*/Ueq
C11.10692 (18)0.3187 (3)0.58894 (13)0.0423 (5)
C21.00700 (19)0.2403 (3)0.60261 (14)0.0430 (5)
C31.00055 (19)0.2195 (3)0.68847 (14)0.0468 (5)
H30.93460.16400.69770.056*
C41.0936 (2)0.2824 (3)0.76021 (14)0.0467 (5)
C51.1917 (2)0.3657 (4)0.74797 (15)0.0518 (5)
H51.25320.40950.79720.062*
C61.19799 (19)0.3834 (3)0.66157 (14)0.0494 (5)
H61.26400.43930.65260.059*
C71.19791 (18)0.2587 (3)0.47727 (14)0.0435 (5)
C81.16867 (18)0.2425 (3)0.37893 (13)0.0414 (5)
C91.25501 (19)0.1698 (3)0.34566 (15)0.0477 (5)
H91.32920.13730.38530.057*
C101.2311 (2)0.1459 (3)0.25453 (15)0.0516 (5)
H101.28950.09590.23330.062*
C111.1218 (2)0.1949 (3)0.19339 (15)0.0476 (5)
C121.0350 (2)0.2662 (3)0.22694 (15)0.0488 (5)
H120.96070.29820.18720.059*
C131.05811 (19)0.2900 (3)0.31857 (14)0.0453 (5)
H130.99940.33810.34000.054*
C141.0983 (3)0.1717 (4)0.09364 (16)0.0683 (7)
H14A1.13790.06220.08300.082*
H14B1.12780.27820.07060.082*
H14C1.01410.16010.06380.082*
O11.10552 (13)0.3344 (2)0.50051 (9)0.0475 (4)
O21.28845 (15)0.2095 (3)0.53218 (11)0.0657 (5)
Cl10.88757 (5)0.17361 (9)0.51123 (4)0.0578 (2)
Cl21.08550 (6)0.25810 (11)0.86852 (4)0.0663 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0423 (11)0.0501 (11)0.0367 (10)0.0031 (9)0.0156 (9)0.0014 (8)
C20.0395 (11)0.0474 (11)0.0395 (11)0.0011 (8)0.0092 (9)0.0015 (8)
C30.0432 (11)0.0534 (12)0.0472 (12)0.0009 (9)0.0191 (10)0.0026 (9)
C40.0473 (12)0.0579 (12)0.0374 (11)0.0079 (10)0.0173 (9)0.0031 (9)
C50.0461 (12)0.0662 (14)0.0395 (11)0.0022 (11)0.0087 (9)0.0052 (10)
C60.0427 (11)0.0618 (13)0.0448 (11)0.0077 (10)0.0153 (9)0.0017 (10)
C70.0361 (10)0.0530 (12)0.0422 (11)0.0051 (8)0.0134 (9)0.0009 (8)
C80.0389 (11)0.0463 (11)0.0401 (11)0.0034 (8)0.0144 (9)0.0006 (8)
C90.0373 (10)0.0585 (13)0.0485 (12)0.0010 (9)0.0156 (9)0.0021 (9)
C100.0479 (12)0.0603 (13)0.0545 (13)0.0012 (10)0.0273 (10)0.0027 (10)
C110.0526 (12)0.0521 (12)0.0421 (11)0.0049 (10)0.0210 (10)0.0032 (9)
C120.0428 (11)0.0593 (13)0.0424 (11)0.0017 (10)0.0108 (9)0.0001 (9)
C130.0410 (11)0.0544 (12)0.0440 (11)0.0037 (9)0.0185 (9)0.0006 (9)
C140.0794 (18)0.0868 (19)0.0411 (13)0.0041 (15)0.0227 (12)0.0068 (12)
O10.0447 (8)0.0631 (10)0.0360 (7)0.0046 (7)0.0150 (6)0.0030 (6)
O20.0422 (9)0.1043 (14)0.0445 (9)0.0114 (9)0.0054 (7)0.0046 (9)
Cl10.0448 (3)0.0756 (5)0.0471 (3)0.0110 (3)0.0066 (2)0.0050 (2)
Cl20.0661 (4)0.0979 (6)0.0391 (3)0.0083 (3)0.0225 (3)0.0052 (3)
Geometric parameters (Å, º) top
C1—C61.375 (3)C8—C91.391 (3)
C1—O11.384 (2)C8—C131.391 (3)
C1—C21.389 (3)C9—C101.373 (3)
C2—C31.379 (3)C9—H90.9300
C2—Cl11.728 (2)C10—C111.388 (3)
C3—C41.375 (3)C10—H100.9300
C3—H30.9300C11—C121.394 (3)
C4—C51.375 (3)C11—C141.505 (3)
C4—Cl21.738 (2)C12—C131.382 (3)
C5—C61.384 (3)C12—H120.9300
C5—H50.9300C13—H130.9300
C6—H60.9300C14—H14A0.9600
C7—O21.194 (3)C14—H14B0.9600
C7—O11.373 (3)C14—H14C0.9600
C7—C81.470 (3)
C6—C1—O1123.66 (19)C13—C8—C7123.14 (19)
C6—C1—C2119.54 (19)C10—C9—C8120.3 (2)
O1—C1—C2116.72 (18)C10—C9—H9119.9
C3—C2—C1120.70 (19)C8—C9—H9119.9
C3—C2—Cl1119.37 (17)C9—C10—C11121.4 (2)
C1—C2—Cl1119.91 (16)C9—C10—H10119.3
C4—C3—C2118.7 (2)C11—C10—H10119.3
C4—C3—H3120.7C10—C11—C12118.22 (19)
C2—C3—H3120.7C10—C11—C14120.6 (2)
C3—C4—C5121.55 (19)C12—C11—C14121.2 (2)
C3—C4—Cl2118.88 (17)C13—C12—C11120.8 (2)
C5—C4—Cl2119.56 (17)C13—C12—H12119.6
C4—C5—C6119.3 (2)C11—C12—H12119.6
C4—C5—H5120.4C12—C13—C8120.3 (2)
C6—C5—H5120.4C12—C13—H13119.8
C1—C6—C5120.2 (2)C8—C13—H13119.8
C1—C6—H6119.9C11—C14—H14A109.5
C5—C6—H6119.9C11—C14—H14B109.5
O2—C7—O1122.5 (2)H14A—C14—H14B109.5
O2—C7—C8125.9 (2)C11—C14—H14C109.5
O1—C7—C8111.61 (17)H14A—C14—H14C109.5
C9—C8—C13118.99 (19)H14B—C14—H14C109.5
C9—C8—C7117.83 (18)C7—O1—C1118.52 (16)
C6—C1—C2—C32.9 (3)O1—C7—C8—C133.1 (3)
O1—C1—C2—C3179.89 (19)C13—C8—C9—C100.1 (3)
C6—C1—C2—Cl1175.41 (18)C7—C8—C9—C10177.9 (2)
O1—C1—C2—Cl11.6 (3)C8—C9—C10—C110.7 (4)
C1—C2—C3—C41.8 (3)C9—C10—C11—C121.2 (4)
Cl1—C2—C3—C4176.53 (17)C9—C10—C11—C14178.6 (2)
C2—C3—C4—C50.3 (3)C10—C11—C12—C130.9 (3)
C2—C3—C4—Cl2179.53 (17)C14—C11—C12—C13178.9 (2)
C3—C4—C5—C61.2 (4)C11—C12—C13—C80.2 (3)
Cl2—C4—C5—C6179.54 (18)C9—C8—C13—C120.4 (3)
O1—C1—C6—C5178.7 (2)C7—C8—C13—C12178.0 (2)
C2—C1—C6—C51.9 (3)O2—C7—O1—C113.5 (3)
C4—C5—C6—C10.1 (4)C8—C7—O1—C1164.82 (18)
O2—C7—C8—C92.5 (3)C6—C1—O1—C757.5 (3)
O1—C7—C8—C9179.25 (18)C2—C1—O1—C7125.6 (2)
O2—C7—C8—C13175.1 (2)

Experimental details

Crystal data
Chemical formulaC14H10Cl2O2
Mr281.12
Crystal system, space groupMonoclinic, P21/n
Temperature (K)299
a, b, c (Å)11.854 (1), 7.2039 (9), 15.653 (2)
β (°) 108.670 (9)
V3)1266.3 (3)
Z4
Radiation typeCu Kα
µ (mm1)4.53
Crystal size (mm)0.55 × 0.53 × 0.18
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.159, 0.443
No. of measured, independent and
observed [I > 2σ(I)] reflections
4377, 2265, 2027
Rint0.034
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.130, 1.05
No. of reflections2265
No. of parameters165
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.40, 0.41

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

 

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