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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

2-(4-Chloro­phen­yl)-2-oxo­ethyl 2,4-di­fluoro­benzoate

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bOrganic Chemistry Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India, and cDepartment of Physics, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India
*Correspondence e-mail: hkfun@usm.my

(Received 26 May 2011; accepted 30 May 2011; online 11 June 2011)

The asymmetric unit of title compound, C15H9ClF2O3, consists of two crystallographically independent mol­ecules. The dihedral angle between the two terminal benzene rings in one mol­ecule is 7.92 (14)°, while that in the other mol­ecule is 73.50 (16)°. In the crystal, mol­ecules are stacked into columns along the b axis by inter­molecular C—H⋯O hydrogen bonds. A ππ inter­action with a centroid-to-centroid distance of 3.747 (2) Å further stabilizes the crystal structure.

Related literature

For background to and applications of phenacyl benzoates, see: Rather & Reid (1919[Rather, J. B. & Reid, E. (1919). J. Am. Chem. Soc. 41, 75-83.]); Sheehan & Umezaw (1973[Sheehan, J. C. & Umezaw, K. (1973). J. Org. Chem. 58, 3771-3773.]); Ruzicka et al. (2002[Ruzicka, R., Zabadal, M. & Klan, P. (2002). Synth. Commun. 32, 2581-2590.]); Litera et al. (2006[Litera, J. K., Loya, A. D. & Klan, P. (2006). J. Org. Chem. 71, 713-723.]); Huang et al. (1996[Huang, W., Pian, J., Chen, B., Pei, W. & Ye, X. (1996). Tetrahedron, 52, 10131-10136.]); Gandhi et al. (1995[Gandhi, S. S., Bell, K. L. & Gibson, M. S. (1995). Tetrahedron, 51, 13301-13308.]). For reference bond-length values, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C15H9ClF2O3

  • Mr = 310.67

  • Monoclinic, P 21 /c

  • a = 16.0179 (17) Å

  • b = 7.9609 (8) Å

  • c = 24.0172 (18) Å

  • β = 115.939 (5)°

  • V = 2754.1 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.31 mm−1

  • T = 296 K

  • 0.55 × 0.26 × 0.09 mm

Data collection
  • Bruker SMART APEXII DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.850, Tmax = 0.974

  • 17424 measured reflections

  • 6308 independent reflections

  • 3353 reflections with I > 2σ(I)

  • Rint = 0.030

Refinement
  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.206

  • S = 1.03

  • 6308 reflections

  • 379 parameters

  • H-atom parameters constrained

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C8A—H8AB⋯O3B 0.97 2.60 3.451 (4) 147
C8A—H8AA⋯O1Bi 0.97 2.42 3.294 (3) 149
C5B—H5BA⋯O3Aii 0.93 2.50 3.376 (4) 158
C8B—H8BB⋯O3Aii 0.97 2.58 3.415 (3) 144
C14B—H14B⋯O1Aiii 0.93 2.59 3.216 (5) 125
Symmetry codes: (i) x, y-1, z; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Phenacyl benzoates derivatives are very important in identification of organic acids (Rather & Reid, 1919), they undergo photolysis in neutral and mild conditions (Sheehan & Umezaw, 1973; Ruzicka et al., 2002; Litera et al., 2006). They find applications in the field of synthetic chemistry for the synthesis of oxazoles, imidazoles (Huang et al., 1996), benzoxazepine (Gandhi et al., 1995). We hereby report the crystal structure of 2-(4-chlorophenyl)-2-oxoethyl 2,4-difluorobenzoate of potential commercial importance.

The asymmetric unit of the title compound (Fig. 1), consists of two crystallographically independent molecules A and B. Both terminal phenyl rings (C1–C6 and C10–C15) in molecules A and B make dihedral angles of 7.92 (14) and 73.50 (16)° to each other, respectively. The bond lengths (Allen et al., 1987) and angles are within normal ranges.

The crystal packing is shown in Fig. 2. The intermolecular C8A—H8AB···O3B hydrogen bond linked the molecule A with molecule B together. The molecules are linked into columns along the b axis by the intermolecular C8A—H8AA···O1B, C5B—H5BA···O3A, C8B—H8BB···O3A and C14B—H14B···O1A hydrogen bonds (Table 1). A ππ interaction further stabilizes the crystal structure [Cg1···Cg2ii = 3.747 (2) Å; Cg1 and Cg2 are centroids of C1B–C6B and C10B–C15B benzene ring, respectively].

Related literature top

For background to and applications of phenacyl benzoates, see: Rather & Reid (1919); Sheehan & Umezaw (1973); Ruzicka et al. (2002); Litera et al. (2006); Huang et al. (1996); Gandhi et al. (1995). For reference bond-length values, see: Allen et al. (1987).

Experimental top

A mixture of 2,4-difluorobenzoic acid (1.0 g, 0.0063 mol) potassium carbonate (0.95 g, 0.0069 mol) and 2-bromo-1-(4-chlorophenyl)ethanone (1.41 g, 0.0063 mol) in dimethylformamide (10 ml) was stirred at room temperature for 2 h. On cooling, colourless needle-shaped crystals 2-(4-chlorophenyl)-2-oxoethyl 2,4-difluorobenzoate begin to separate. It was collected by filtration and recrystallized from ethanol. Yield: 1.65 g, 84.1%. M.p.: 376–377 K.

Refinement top

All H atoms were positioned geometrically (C—H = 0.93 or 0.97 Å) and refined using a riding model with Uiso(H) = 1.2Ueq(C). Four reflections, -6 4 4, -6 5 8, -1 1 1 and -1 4 10, were omitted.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing two independent molecules with atom labels with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing of the title compound. Dashed lines represent the hydrogen bonds.
2-(4-Chlorophenyl)-2-oxoethyl 2,4-difluorobenzoate top
Crystal data top
C15H9ClF2O3F(000) = 1264
Mr = 310.67Dx = 1.499 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3882 reflections
a = 16.0179 (17) Åθ = 2.6–22.5°
b = 7.9609 (8) ŵ = 0.31 mm1
c = 24.0172 (18) ÅT = 296 K
β = 115.939 (5)°Needle, colourless
V = 2754.1 (5) Å30.55 × 0.26 × 0.09 mm
Z = 8
Data collection top
Bruker SMART APEXII DUO CCD area-detector
diffractometer
6308 independent reflections
Radiation source: fine-focus sealed tube3353 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ϕ and ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 2019
Tmin = 0.850, Tmax = 0.974k = 1010
17424 measured reflectionsl = 3131
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.206H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.114P)2 + 0.0306P]
where P = (Fo2 + 2Fc2)/3
6308 reflections(Δ/σ)max = 0.001
379 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C15H9ClF2O3V = 2754.1 (5) Å3
Mr = 310.67Z = 8
Monoclinic, P21/cMo Kα radiation
a = 16.0179 (17) ŵ = 0.31 mm1
b = 7.9609 (8) ÅT = 296 K
c = 24.0172 (18) Å0.55 × 0.26 × 0.09 mm
β = 115.939 (5)°
Data collection top
Bruker SMART APEXII DUO CCD area-detector
diffractometer
6308 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3353 reflections with I > 2σ(I)
Tmin = 0.850, Tmax = 0.974Rint = 0.030
17424 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.206H-atom parameters constrained
S = 1.03Δρmax = 0.33 e Å3
6308 reflectionsΔρmin = 0.32 e Å3
379 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
Cl1A0.01833 (6)0.69373 (15)0.67059 (4)0.1116 (4)
F1A0.77697 (12)0.3081 (3)1.00087 (8)0.1006 (6)
F2A0.80582 (16)0.0433 (3)1.16292 (10)0.1139 (7)
O1A0.32955 (14)0.3728 (3)0.93888 (9)0.0827 (6)
O2A0.49808 (12)0.3539 (2)0.95029 (8)0.0654 (5)
O3A0.60473 (13)0.3792 (3)0.91508 (8)0.0869 (7)
C1A0.1715 (2)0.4728 (4)0.83169 (14)0.0734 (8)
H1AA0.16150.40760.86030.088*
C2A0.0965 (2)0.5297 (4)0.77968 (15)0.0828 (9)
H2AA0.03640.50100.77270.099*
C3A0.11135 (19)0.6286 (4)0.73861 (13)0.0718 (7)
C4A0.1996 (2)0.6748 (4)0.74836 (13)0.0710 (7)
H4AA0.20860.74610.72080.085*
C5A0.27448 (19)0.6134 (4)0.79980 (12)0.0661 (7)
H5AA0.33430.64130.80610.079*
C6A0.26202 (17)0.5109 (3)0.84226 (11)0.0570 (6)
C7A0.34074 (18)0.4379 (3)0.89723 (11)0.0589 (6)
C8A0.43456 (17)0.4445 (3)0.89777 (11)0.0608 (6)
H8AA0.43190.39490.86010.073*
H8AB0.45470.56030.89990.073*
C9A0.58203 (18)0.3275 (3)0.95319 (11)0.0590 (6)
C10A0.64078 (17)0.2283 (3)1.00863 (11)0.0573 (6)
C11A0.73636 (19)0.2215 (4)1.03031 (12)0.0667 (7)
C12A0.7933 (2)0.1312 (4)1.08180 (13)0.0754 (8)
H12A0.85720.12851.09540.091*
C13A0.7515 (2)0.0455 (4)1.11226 (13)0.0760 (8)
C14A0.6584 (2)0.0462 (4)1.09386 (13)0.0758 (8)
H14A0.63250.01521.11540.091*
C15A0.6027 (2)0.1400 (3)1.04240 (12)0.0649 (7)
H15A0.53900.14441.03010.078*
Cl1B0.01753 (7)1.09979 (18)0.57396 (5)0.1307 (5)
F1B0.70241 (15)1.0849 (3)0.83037 (10)0.1280 (9)
F2B0.92324 (16)0.8868 (4)1.01835 (10)0.1338 (8)
O1B0.41561 (18)1.1476 (3)0.79738 (10)0.1000 (7)
O2B0.54117 (14)0.9566 (3)0.78473 (8)0.0834 (6)
O3B0.49789 (16)0.8028 (3)0.84487 (11)0.1036 (8)
C1B0.2248 (3)1.1648 (4)0.71976 (14)0.0828 (9)
H1BA0.24671.21990.75770.099*
C2B0.1322 (3)1.1733 (5)0.67968 (16)0.0935 (10)
H2BA0.09151.23410.69020.112*
C3B0.1000 (2)1.0906 (4)0.62378 (13)0.0838 (9)
C4B0.1590 (2)1.0031 (4)0.60703 (12)0.0816 (9)
H4BA0.13650.94950.56880.098*
C5B0.2515 (2)0.9953 (4)0.64709 (11)0.0717 (7)
H5BA0.29160.93570.63580.086*
C6B0.2865 (2)1.0750 (3)0.70449 (11)0.0644 (7)
C7B0.3848 (2)1.0667 (3)0.74964 (12)0.0696 (7)
C8B0.4479 (2)0.9489 (5)0.73696 (12)0.0805 (9)
H8BA0.42480.83500.73390.097*
H8BB0.44750.97780.69760.097*
C9B0.5572 (2)0.8795 (4)0.83760 (13)0.0702 (7)
C10B0.65445 (19)0.8922 (3)0.88491 (12)0.0629 (7)
C11B0.7239 (2)0.9844 (4)0.88009 (13)0.0757 (8)
C12B0.8133 (2)0.9838 (5)0.92315 (15)0.0882 (9)
H12B0.85821.04660.91790.106*
C13B0.8352 (2)0.8877 (5)0.97465 (14)0.0862 (9)
C14B0.7698 (3)0.7944 (4)0.98378 (14)0.0864 (9)
H14B0.78580.73001.01930.104*
C15B0.6810 (2)0.8001 (4)0.93878 (13)0.0757 (8)
H15B0.63590.73900.94450.091*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0784 (6)0.1292 (9)0.1112 (7)0.0192 (5)0.0266 (5)0.0172 (6)
F1A0.0685 (11)0.1358 (18)0.1080 (13)0.0061 (10)0.0484 (10)0.0250 (11)
F2A0.1271 (17)0.1155 (17)0.1067 (13)0.0402 (13)0.0580 (13)0.0393 (12)
O1A0.0813 (13)0.0993 (16)0.0837 (12)0.0051 (11)0.0511 (11)0.0162 (11)
O2A0.0666 (11)0.0714 (12)0.0692 (10)0.0014 (9)0.0398 (9)0.0027 (9)
O3A0.0691 (12)0.130 (2)0.0746 (11)0.0026 (11)0.0432 (10)0.0174 (11)
C1A0.0694 (18)0.0748 (19)0.0922 (18)0.0099 (15)0.0504 (16)0.0013 (15)
C2A0.0612 (17)0.091 (2)0.107 (2)0.0066 (15)0.0467 (17)0.0037 (18)
C3A0.0655 (17)0.0686 (18)0.0827 (17)0.0034 (14)0.0337 (14)0.0080 (14)
C4A0.0788 (19)0.0675 (18)0.0772 (16)0.0013 (14)0.0437 (15)0.0051 (14)
C5A0.0656 (16)0.0652 (17)0.0790 (16)0.0064 (13)0.0420 (14)0.0023 (13)
C6A0.0631 (15)0.0524 (14)0.0665 (13)0.0075 (11)0.0386 (12)0.0110 (11)
C7A0.0722 (17)0.0505 (14)0.0670 (14)0.0098 (12)0.0426 (13)0.0107 (12)
C8A0.0652 (16)0.0622 (16)0.0629 (13)0.0041 (12)0.0352 (12)0.0022 (12)
C9A0.0619 (15)0.0620 (16)0.0619 (13)0.0168 (12)0.0352 (12)0.0134 (12)
C10A0.0647 (15)0.0523 (15)0.0632 (13)0.0099 (12)0.0356 (12)0.0121 (11)
C11A0.0684 (17)0.0688 (18)0.0739 (15)0.0073 (14)0.0414 (14)0.0037 (13)
C12A0.0723 (18)0.078 (2)0.0825 (17)0.0069 (15)0.0396 (15)0.0008 (15)
C13A0.096 (2)0.0638 (18)0.0739 (16)0.0151 (16)0.0419 (16)0.0045 (14)
C14A0.099 (2)0.0632 (18)0.0848 (18)0.0055 (16)0.0580 (18)0.0019 (15)
C15A0.0722 (17)0.0585 (16)0.0745 (15)0.0096 (13)0.0416 (14)0.0075 (13)
Cl1B0.0942 (7)0.1856 (13)0.1040 (7)0.0478 (7)0.0356 (6)0.0041 (7)
F1B0.1063 (16)0.154 (2)0.1211 (15)0.0321 (14)0.0474 (13)0.0536 (14)
F2B0.0901 (15)0.181 (2)0.1081 (15)0.0141 (15)0.0231 (13)0.0130 (15)
O1B0.1165 (19)0.0871 (16)0.0938 (15)0.0155 (13)0.0435 (14)0.0334 (12)
O2B0.0794 (14)0.1104 (17)0.0709 (11)0.0151 (12)0.0426 (11)0.0034 (11)
O3B0.0879 (16)0.0978 (17)0.1253 (18)0.0294 (13)0.0468 (14)0.0205 (14)
C1B0.109 (3)0.075 (2)0.0801 (18)0.0001 (17)0.0553 (19)0.0151 (15)
C2B0.106 (3)0.095 (3)0.096 (2)0.026 (2)0.059 (2)0.0040 (19)
C3B0.085 (2)0.097 (2)0.0764 (17)0.0228 (17)0.0423 (16)0.0098 (16)
C4B0.087 (2)0.102 (2)0.0608 (15)0.0152 (17)0.0365 (16)0.0038 (15)
C5B0.085 (2)0.078 (2)0.0655 (15)0.0082 (15)0.0451 (15)0.0012 (13)
C6B0.0864 (19)0.0554 (16)0.0664 (14)0.0021 (13)0.0472 (14)0.0018 (12)
C7B0.093 (2)0.0588 (17)0.0702 (15)0.0190 (14)0.0481 (16)0.0099 (13)
C8B0.077 (2)0.103 (2)0.0665 (15)0.0066 (16)0.0357 (15)0.0138 (15)
C9B0.0790 (19)0.0623 (17)0.0821 (17)0.0141 (15)0.0470 (15)0.0104 (14)
C10B0.0774 (18)0.0541 (16)0.0727 (15)0.0107 (13)0.0473 (14)0.0084 (12)
C11B0.089 (2)0.0713 (19)0.0778 (17)0.0086 (16)0.0466 (17)0.0091 (15)
C12B0.080 (2)0.100 (3)0.094 (2)0.0243 (18)0.0477 (18)0.0006 (19)
C13B0.075 (2)0.103 (3)0.0771 (18)0.0093 (18)0.0295 (16)0.0089 (17)
C14B0.107 (3)0.086 (2)0.0711 (17)0.0115 (19)0.0433 (18)0.0055 (16)
C15B0.095 (2)0.0682 (19)0.0792 (17)0.0194 (15)0.0523 (17)0.0038 (14)
Geometric parameters (Å, º) top
Cl1A—C3A1.740 (3)Cl1B—C3B1.735 (3)
F1A—C11A1.342 (3)F1B—C11B1.351 (3)
F2A—C13A1.346 (3)F2B—C13B1.340 (4)
O1A—C7A1.207 (3)O1B—C7B1.216 (3)
O2A—C9A1.332 (3)O2B—C9B1.330 (3)
O2A—C8A1.423 (3)O2B—C8B1.432 (3)
O3A—C9A1.196 (3)O3B—C9B1.204 (3)
C1A—C2A1.377 (4)C1B—C2B1.372 (5)
C1A—C6A1.392 (4)C1B—C6B1.393 (4)
C1A—H1AA0.9300C1B—H1BA0.9300
C2A—C3A1.362 (4)C2B—C3B1.377 (5)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.378 (4)C3B—C4B1.368 (4)
C4A—C5A1.381 (4)C4B—C5B1.370 (4)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.387 (3)C5B—C6B1.393 (3)
C5A—H5AA0.9300C5B—H5BA0.9300
C6A—C7A1.488 (4)C6B—C7B1.472 (4)
C7A—C8A1.498 (3)C7B—C8B1.504 (4)
C8A—H8AA0.9700C8B—H8BA0.9700
C8A—H8AB0.9700C8B—H8BB0.9700
C9A—C10A1.479 (4)C9B—C10B1.477 (4)
C10A—C11A1.386 (4)C10B—C11B1.380 (4)
C10A—C15A1.399 (3)C10B—C15B1.382 (4)
C11A—C12A1.375 (4)C11B—C12B1.350 (4)
C12A—C13A1.370 (4)C12B—C13B1.363 (4)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.357 (4)C13B—C14B1.378 (5)
C14A—C15A1.384 (4)C14B—C15B1.360 (4)
C14A—H14A0.9300C14B—H14B0.9300
C15A—H15A0.9300C15B—H15B0.9300
C9A—O2A—C8A116.13 (18)C9B—O2B—C8B116.3 (2)
C2A—C1A—C6A121.3 (3)C2B—C1B—C6B121.0 (3)
C2A—C1A—H1AA119.3C2B—C1B—H1BA119.5
C6A—C1A—H1AA119.3C6B—C1B—H1BA119.5
C3A—C2A—C1A119.2 (3)C1B—C2B—C3B119.3 (3)
C3A—C2A—H2AA120.4C1B—C2B—H2BA120.4
C1A—C2A—H2AA120.4C3B—C2B—H2BA120.4
C2A—C3A—C4A121.5 (3)C4B—C3B—C2B121.2 (3)
C2A—C3A—Cl1A120.2 (2)C4B—C3B—Cl1B120.0 (2)
C4A—C3A—Cl1A118.3 (2)C2B—C3B—Cl1B118.8 (2)
C3A—C4A—C5A118.8 (3)C3B—C4B—C5B119.4 (3)
C3A—C4A—H4AA120.6C3B—C4B—H4BA120.3
C5A—C4A—H4AA120.6C5B—C4B—H4BA120.3
C4A—C5A—C6A121.2 (2)C4B—C5B—C6B121.2 (3)
C4A—C5A—H5AA119.4C4B—C5B—H5BA119.4
C6A—C5A—H5AA119.4C6B—C5B—H5BA119.4
C5A—C6A—C1A117.9 (3)C1B—C6B—C5B118.0 (3)
C5A—C6A—C7A122.9 (2)C1B—C6B—C7B118.9 (2)
C1A—C6A—C7A119.2 (2)C5B—C6B—C7B123.1 (2)
O1A—C7A—C6A121.8 (2)O1B—C7B—C6B122.2 (3)
O1A—C7A—C8A121.3 (2)O1B—C7B—C8B119.3 (3)
C6A—C7A—C8A116.85 (19)C6B—C7B—C8B118.4 (2)
O2A—C8A—C7A108.40 (19)O2B—C8B—C7B111.6 (2)
O2A—C8A—H8AA110.0O2B—C8B—H8BA109.3
C7A—C8A—H8AA110.0C7B—C8B—H8BA109.3
O2A—C8A—H8AB110.0O2B—C8B—H8BB109.3
C7A—C8A—H8AB110.0C7B—C8B—H8BB109.3
H8AA—C8A—H8AB108.4H8BA—C8B—H8BB108.0
O3A—C9A—O2A122.9 (2)O3B—C9B—O2B122.5 (3)
O3A—C9A—C10A125.9 (2)O3B—C9B—C10B123.8 (3)
O2A—C9A—C10A111.19 (19)O2B—C9B—C10B113.6 (2)
C11A—C10A—C15A116.9 (2)C11B—C10B—C15B115.6 (3)
C11A—C10A—C9A121.5 (2)C11B—C10B—C9B126.2 (2)
C15A—C10A—C9A121.5 (2)C15B—C10B—C9B118.2 (2)
F1A—C11A—C12A117.3 (2)C12B—C11B—F1B117.0 (3)
F1A—C11A—C10A119.5 (2)C12B—C11B—C10B123.9 (3)
C12A—C11A—C10A123.2 (2)F1B—C11B—C10B119.1 (3)
C13A—C12A—C11A117.0 (3)C11B—C12B—C13B117.6 (3)
C13A—C12A—H12A121.5C11B—C12B—H12B121.2
C11A—C12A—H12A121.5C13B—C12B—H12B121.2
F2A—C13A—C14A118.7 (3)F2B—C13B—C12B118.6 (3)
F2A—C13A—C12A118.1 (3)F2B—C13B—C14B119.0 (3)
C14A—C13A—C12A123.2 (3)C12B—C13B—C14B122.3 (3)
C13A—C14A—C15A118.7 (3)C15B—C14B—C13B117.3 (3)
C13A—C14A—H14A120.7C15B—C14B—H14B121.3
C15A—C14A—H14A120.7C13B—C14B—H14B121.3
C14A—C15A—C10A121.0 (3)C14B—C15B—C10B123.3 (3)
C14A—C15A—H15A119.5C14B—C15B—H15B118.4
C10A—C15A—H15A119.5C10B—C15B—H15B118.4
C6A—C1A—C2A—C3A1.6 (5)C6B—C1B—C2B—C3B0.4 (5)
C1A—C2A—C3A—C4A0.9 (5)C1B—C2B—C3B—C4B1.3 (5)
C1A—C2A—C3A—Cl1A176.8 (2)C1B—C2B—C3B—Cl1B179.1 (3)
C2A—C3A—C4A—C5A2.6 (4)C2B—C3B—C4B—C5B1.1 (5)
Cl1A—C3A—C4A—C5A175.1 (2)Cl1B—C3B—C4B—C5B179.3 (3)
C3A—C4A—C5A—C6A1.8 (4)C3B—C4B—C5B—C6B0.1 (5)
C4A—C5A—C6A—C1A0.5 (4)C2B—C1B—C6B—C5B0.5 (4)
C4A—C5A—C6A—C7A178.1 (2)C2B—C1B—C6B—C7B178.6 (3)
C2A—C1A—C6A—C5A2.3 (4)C4B—C5B—C6B—C1B0.7 (4)
C2A—C1A—C6A—C7A176.4 (3)C4B—C5B—C6B—C7B178.4 (3)
C5A—C6A—C7A—O1A167.5 (2)C1B—C6B—C7B—O1B6.7 (4)
C1A—C6A—C7A—O1A13.9 (4)C5B—C6B—C7B—O1B174.1 (3)
C5A—C6A—C7A—C8A14.2 (3)C1B—C6B—C7B—C8B170.9 (3)
C1A—C6A—C7A—C8A164.4 (2)C5B—C6B—C7B—C8B8.2 (4)
C9A—O2A—C8A—C7A171.1 (2)C9B—O2B—C8B—C7B75.9 (3)
O1A—C7A—C8A—O2A4.4 (3)O1B—C7B—C8B—O2B2.8 (4)
C6A—C7A—C8A—O2A173.96 (19)C6B—C7B—C8B—O2B179.4 (2)
C8A—O2A—C9A—O3A1.6 (4)C8B—O2B—C9B—O3B2.2 (4)
C8A—O2A—C9A—C10A178.4 (2)C8B—O2B—C9B—C10B179.9 (2)
O3A—C9A—C10A—C11A16.9 (4)O3B—C9B—C10B—C11B176.8 (3)
O2A—C9A—C10A—C11A163.1 (2)O2B—C9B—C10B—C11B5.3 (4)
O3A—C9A—C10A—C15A164.6 (3)O3B—C9B—C10B—C15B5.4 (4)
O2A—C9A—C10A—C15A15.4 (3)O2B—C9B—C10B—C15B172.5 (2)
C15A—C10A—C11A—F1A177.9 (2)C15B—C10B—C11B—C12B2.1 (4)
C9A—C10A—C11A—F1A0.7 (4)C9B—C10B—C11B—C12B175.8 (3)
C15A—C10A—C11A—C12A1.1 (4)C15B—C10B—C11B—F1B176.4 (3)
C9A—C10A—C11A—C12A179.7 (2)C9B—C10B—C11B—F1B5.7 (4)
F1A—C11A—C12A—C13A178.9 (3)F1B—C11B—C12B—C13B177.6 (3)
C10A—C11A—C12A—C13A0.2 (4)C10B—C11B—C12B—C13B0.9 (5)
C11A—C12A—C13A—F2A179.8 (2)C11B—C12B—C13B—F2B179.2 (3)
C11A—C12A—C13A—C14A0.1 (4)C11B—C12B—C13B—C14B0.5 (5)
F2A—C13A—C14A—C15A178.8 (2)F2B—C13B—C14B—C15B179.2 (3)
C12A—C13A—C14A—C15A1.1 (4)C12B—C13B—C14B—C15B0.5 (5)
C13A—C14A—C15A—C10A2.1 (4)C13B—C14B—C15B—C10B0.9 (5)
C11A—C10A—C15A—C14A2.1 (4)C11B—C10B—C15B—C14B2.1 (4)
C9A—C10A—C15A—C14A179.4 (2)C9B—C10B—C15B—C14B176.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8A—H8AB···O3B0.972.603.451 (4)147
C8A—H8AA···O1Bi0.972.423.294 (3)149
C5B—H5BA···O3Aii0.932.503.376 (4)158
C8B—H8BB···O3Aii0.972.583.415 (3)144
C14B—H14B···O1Aiii0.932.593.216 (5)125
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1/2, z+3/2; (iii) x+1, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC15H9ClF2O3
Mr310.67
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)16.0179 (17), 7.9609 (8), 24.0172 (18)
β (°) 115.939 (5)
V3)2754.1 (5)
Z8
Radiation typeMo Kα
µ (mm1)0.31
Crystal size (mm)0.55 × 0.26 × 0.09
Data collection
DiffractometerBruker SMART APEXII DUO CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.850, 0.974
No. of measured, independent and
observed [I > 2σ(I)] reflections
17424, 6308, 3353
Rint0.030
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.206, 1.03
No. of reflections6308
No. of parameters379
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.32

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8A—H8AB···O3B0.97002.60003.451 (4)147.00
C8A—H8AA···O1Bi0.97002.42003.294 (3)149.00
C5B—H5BA···O3Aii0.93002.50003.376 (4)158.00
C8B—H8BB···O3Aii0.97002.58003.415 (3)144.00
C14B—H14B···O1Aiii0.93002.59003.216 (5)125.00
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1/2, z+3/2; (iii) x+1, y+1, z+2.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for Research University Grant No. 1001/PFIZIK/811160. SA thanks the Malaysian government and USM for the award of a research scholarship. AMI is grateful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for a Young Scientist Award. BG thanks the Department of Information Technology, New Delhi, India, for financial support.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationGandhi, S. S., Bell, K. L. & Gibson, M. S. (1995). Tetrahedron, 51, 13301–13308.  CrossRef CAS Web of Science Google Scholar
First citationHuang, W., Pian, J., Chen, B., Pei, W. & Ye, X. (1996). Tetrahedron, 52, 10131–10136.  CrossRef CAS Web of Science Google Scholar
First citationLitera, J. K., Loya, A. D. & Klan, P. (2006). J. Org. Chem. 71, 713–723.  Web of Science PubMed Google Scholar
First citationRather, J. B. & Reid, E. (1919). J. Am. Chem. Soc. 41, 75–83.  CrossRef CAS Google Scholar
First citationRuzicka, R., Zabadal, M. & Klan, P. (2002). Synth. Commun. 32, 2581–2590.  Web of Science CrossRef CAS Google Scholar
First citationSheehan, J. C. & Umezaw, K. (1973). J. Org. Chem. 58, 3771–3773.  CrossRef Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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