Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The structure of the title compound (23DCPBA), C13H8Cl2O2, resembles that of phenyl benzoate (PBA), 2,6-dichloro­phenyl benzoate (26DCPBA) and 3,4-dichloro­phenyl benzoate (34DCPBA), with similar geometric parameters. The dihedral angle between the phenyl and benzoyl rings in 23DCPBA is 50.16 (7)°, compared to the value of 55.7° for PBA, 75.75 (10)° for 26DCPBA and 53.77 (5)° for 34DCPBA.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048751/bt2526sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048751/bt2526Isup2.hkl
Contains datablock I

CCDC reference: 667331

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C)= 0.004 Å
  • R factor = 0.047
  • wR factor = 0.129
  • Data-to-parameter ratio = 11.7

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 the substituent effects on the structures of aryl benzoates (Gowda, Foro, Babitha & Fuess, 2007a, b, c; Gowda, Foro, Nayak & Fuess, 2007a, Gowda, Foro, Nayak & Fuess, 2007b), the structure of 2,3-dichlorophenyl benzoate (23DCPBA) has been determined. The structure of 23DCPBA (Fig. 1) is similar to those of phenyl benzoate (PBA) (Adams & Morsi, 1976); 2,6-dichlorophenyl benzoate (26DCPBA)(Gowda et al., 2007c); 3,4-dichlorophenyl benzoate (34DCPBA)(Gowda, Foro, Babitha & Fuess, 2007b) and other aryl benzoates (Gowda, Foro, Babitha & Fuess, 2007a; Gowda, Foro, Nayak & Fuess, 2007a, b). The bond parameters in 23DCPBA are similar to those in PBA, 26DCPBA, 34DCPBA and other aryl benzoates. A packing diagram is shown in Fig. 2.

Related literature top

For related literature, see: Adams & Morsi (1976); Gowda, Foro, Babitha et al. (2007a,b,c); Gowda, Foro, Nayak et al. (2007a,b); 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 located in difference map, and their positional parameters were refined with Uiso = 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 aryl benzoates (Gowda, Foro, Babitha & Fuess, 2007a, b, c; Gowda, Foro, Nayak & Fuess, 2007a, Gowda, Foro, Nayak & Fuess, 2007b), the structure of 2,3-dichlorophenyl benzoate (23DCPBA) has been determined. The structure of 23DCPBA (Fig. 1) is similar to those of phenyl benzoate (PBA) (Adams & Morsi, 1976); 2,6-dichlorophenyl benzoate (26DCPBA)(Gowda et al., 2007c); 3,4-dichlorophenyl benzoate (34DCPBA)(Gowda, Foro, Babitha & Fuess, 2007b) and other aryl benzoates (Gowda, Foro, Babitha & Fuess, 2007a; Gowda, Foro, Nayak & Fuess, 2007a, b). The bond parameters in 23DCPBA are similar to those in PBA, 26DCPBA, 34DCPBA and other aryl benzoates. A packing diagram is shown in Fig. 2.

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

Computing details top

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

Figures top
[Figure 1] 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.
[Figure 2] Fig. 2. Packing diagram of the title compound.
2,3-Dichlorophenyl benzoate top
Crystal data top
C13H8Cl2O2F(000) = 544
Mr = 267.09Dx = 1.501 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 10.696 (1) Åθ = 5.4–24.7°
b = 3.9820 (6) ŵ = 4.83 mm1
c = 27.796 (3) ÅT = 299 K
β = 93.045 (8)°Thick needle, colourless
V = 1182.2 (2) Å30.60 × 0.20 × 0.08 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
1896 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.078
Graphite monochromatorθmax = 67.0°, θmin = 3.2°
ω/2θ scansh = 121
Absorption correction: ψ scan
(North et al., 1968)
k = 04
Tmin = 0.370, Tmax = 0.683l = 3333
2351 measured reflections3 standard reflections every 120 min
2100 independent reflections intensity decay: 0.5%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Only H-atom coordinates refined
wR(F2) = 0.129 w = 1/[σ2(Fo2) + (0.0863P)2 + 0.2888P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
2100 reflectionsΔρmax = 0.52 e Å3
179 parametersΔρmin = 0.37 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: 0.0027 (6)
Crystal data top
C13H8Cl2O2V = 1182.2 (2) Å3
Mr = 267.09Z = 4
Monoclinic, P21/cCu Kα radiation
a = 10.696 (1) ŵ = 4.83 mm1
b = 3.9820 (6) ÅT = 299 K
c = 27.796 (3) Å0.60 × 0.20 × 0.08 mm
β = 93.045 (8)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
1896 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.078
Tmin = 0.370, Tmax = 0.6833 standard reflections every 120 min
2351 measured reflections intensity decay: 0.5%
2100 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.129Only H-atom coordinates refined
S = 1.08Δρmax = 0.52 e Å3
2100 reflectionsΔρmin = 0.37 e Å3
179 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
C10.35221 (19)1.1414 (5)0.33167 (8)0.0462 (5)
C20.25186 (19)0.9787 (5)0.35114 (7)0.0441 (5)
C30.15267 (18)0.8761 (5)0.32041 (8)0.0451 (5)
C40.1547 (2)0.9281 (6)0.27142 (8)0.0536 (5)
H40.088 (3)0.836 (8)0.2505 (10)0.064*
C50.2550 (2)1.0901 (7)0.25289 (9)0.0579 (6)
H50.251 (3)1.143 (8)0.2200 (11)0.069*
C60.3542 (2)1.1994 (6)0.28270 (9)0.0554 (6)
H60.414 (3)1.328 (8)0.2692 (10)0.066*
C70.5653 (2)1.1548 (6)0.35963 (8)0.0498 (5)
C80.6490 (2)1.2783 (6)0.39969 (8)0.0490 (5)
C90.7764 (2)1.2084 (8)0.39827 (10)0.0610 (6)
H90.804 (3)1.088 (9)0.3738 (12)0.073*
C100.8569 (3)1.3019 (9)0.43582 (11)0.0720 (8)
H100.948 (3)1.229 (10)0.4369 (12)0.086*
C110.8123 (3)1.4670 (9)0.47510 (11)0.0751 (8)
H110.868 (3)1.529 (10)0.5021 (13)0.090*
C120.6869 (3)1.5410 (9)0.47650 (10)0.0712 (7)
H120.659 (3)1.674 (10)0.5014 (13)0.085*
C130.6047 (2)1.4482 (7)0.43874 (8)0.0578 (6)
H130.516 (3)1.501 (8)0.4386 (10)0.069*
O10.44532 (13)1.2603 (4)0.36404 (6)0.0557 (4)
O20.59487 (17)0.9773 (6)0.32765 (6)0.0752 (6)
Cl10.25156 (6)0.90985 (17)0.412174 (18)0.0618 (2)
Cl20.02437 (5)0.68095 (17)0.34350 (2)0.0618 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0443 (10)0.0418 (11)0.0526 (11)0.0037 (8)0.0033 (9)0.0046 (9)
C20.0472 (10)0.0415 (11)0.0438 (10)0.0086 (8)0.0047 (8)0.0000 (8)
C30.0436 (10)0.0387 (10)0.0533 (11)0.0049 (8)0.0046 (8)0.0010 (8)
C40.0532 (12)0.0538 (13)0.0529 (12)0.0060 (10)0.0066 (10)0.0007 (10)
C50.0636 (14)0.0612 (14)0.0489 (12)0.0071 (11)0.0028 (10)0.0110 (10)
C60.0550 (12)0.0514 (13)0.0604 (13)0.0001 (10)0.0099 (10)0.0088 (10)
C70.0491 (11)0.0500 (12)0.0508 (11)0.0049 (9)0.0078 (9)0.0010 (9)
C80.0461 (11)0.0478 (12)0.0534 (11)0.0029 (9)0.0057 (9)0.0041 (9)
C90.0503 (12)0.0706 (16)0.0623 (13)0.0026 (11)0.0055 (11)0.0028 (12)
C100.0508 (13)0.084 (2)0.0805 (18)0.0093 (13)0.0049 (12)0.0141 (15)
C110.0723 (16)0.088 (2)0.0636 (14)0.0257 (15)0.0107 (13)0.0088 (15)
C120.0787 (17)0.0787 (19)0.0565 (13)0.0171 (15)0.0057 (12)0.0090 (13)
C130.0566 (13)0.0627 (15)0.0546 (12)0.0067 (11)0.0090 (10)0.0047 (11)
O10.0433 (8)0.0604 (10)0.0634 (9)0.0013 (7)0.0028 (7)0.0170 (8)
O20.0637 (10)0.0992 (15)0.0623 (10)0.0254 (10)0.0002 (8)0.0258 (10)
Cl10.0693 (4)0.0726 (4)0.0436 (3)0.0008 (3)0.0055 (2)0.0013 (2)
Cl20.0511 (4)0.0636 (4)0.0713 (4)0.0080 (2)0.0106 (3)0.0025 (3)
Geometric parameters (Å, º) top
C1—C61.382 (3)C7—O11.362 (3)
C1—C21.388 (3)C7—C81.476 (3)
C1—O11.389 (3)C8—C131.384 (3)
C2—C31.388 (3)C8—C91.393 (3)
C2—Cl11.719 (2)C9—C101.369 (4)
C3—C41.379 (3)C9—H90.89 (3)
C3—Cl21.730 (2)C10—C111.381 (5)
C4—C51.375 (4)C10—H101.02 (3)
C4—H40.97 (3)C11—C121.376 (4)
C5—C61.381 (4)C11—H110.97 (4)
C5—H50.94 (3)C12—C131.383 (4)
C6—H60.91 (3)C12—H120.93 (4)
C7—O21.192 (3)C13—H130.97 (3)
C6—C1—C2121.0 (2)O1—C7—C8111.49 (18)
C6—C1—O1122.2 (2)C13—C8—C9119.8 (2)
C2—C1—O1116.67 (19)C13—C8—C7122.4 (2)
C3—C2—C1118.62 (19)C9—C8—C7117.9 (2)
C3—C2—Cl1121.28 (16)C10—C9—C8120.1 (3)
C1—C2—Cl1120.10 (16)C10—C9—H9121 (2)
C4—C3—C2120.8 (2)C8—C9—H9119 (2)
C4—C3—Cl2119.25 (17)C9—C10—C11120.1 (3)
C2—C3—Cl2119.96 (16)C9—C10—H10121 (2)
C5—C4—C3119.6 (2)C11—C10—H10119 (2)
C5—C4—H4121.3 (17)C12—C11—C10120.2 (3)
C3—C4—H4119.0 (17)C12—C11—H11119 (2)
C4—C5—C6120.8 (2)C10—C11—H11121 (2)
C4—C5—H5118.2 (19)C11—C12—C13120.2 (3)
C6—C5—H5120.7 (19)C11—C12—H12120 (2)
C5—C6—C1119.1 (2)C13—C12—H12120 (2)
C5—C6—H6117.4 (18)C12—C13—C8119.7 (2)
C1—C6—H6123.1 (18)C12—C13—H13121.8 (18)
O2—C7—O1122.6 (2)C8—C13—H13118.6 (18)
O2—C7—C8125.9 (2)C7—O1—C1118.89 (17)
C6—C1—C2—C30.3 (3)O1—C7—C8—C136.4 (3)
O1—C1—C2—C3175.68 (18)O2—C7—C8—C96.2 (4)
C6—C1—C2—Cl1179.96 (18)O1—C7—C8—C9175.9 (2)
O1—C1—C2—Cl14.0 (3)C13—C8—C9—C101.3 (4)
C1—C2—C3—C41.4 (3)C7—C8—C9—C10176.5 (3)
Cl1—C2—C3—C4179.01 (17)C8—C9—C10—C110.3 (5)
C1—C2—C3—Cl2178.56 (16)C9—C10—C11—C120.6 (5)
Cl1—C2—C3—Cl21.1 (3)C10—C11—C12—C130.5 (5)
C2—C3—C4—C51.5 (3)C11—C12—C13—C80.5 (4)
Cl2—C3—C4—C5178.46 (19)C9—C8—C13—C121.3 (4)
C3—C4—C5—C60.5 (4)C7—C8—C13—C12176.3 (2)
C4—C5—C6—C10.5 (4)O2—C7—O1—C13.8 (4)
C2—C1—C6—C50.6 (4)C8—C7—O1—C1174.26 (19)
O1—C1—C6—C5176.4 (2)C6—C1—O1—C761.0 (3)
O2—C7—C8—C13171.5 (3)C2—C1—O1—C7123.0 (2)

Experimental details

Crystal data
Chemical formulaC13H8Cl2O2
Mr267.09
Crystal system, space groupMonoclinic, P21/c
Temperature (K)299
a, b, c (Å)10.696 (1), 3.9820 (6), 27.796 (3)
β (°) 93.045 (8)
V3)1182.2 (2)
Z4
Radiation typeCu Kα
µ (mm1)4.83
Crystal size (mm)0.60 × 0.20 × 0.08
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.370, 0.683
No. of measured, independent and
observed [I > 2σ(I)] reflections
2351, 2100, 1896
Rint0.078
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.129, 1.08
No. of reflections2100
No. of parameters179
H-atom treatmentOnly H-atom coordinates refined
Δρmax, Δρmin (e Å3)0.52, 0.37

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

 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds