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Acta Cryst. (2008). E64, o1720-o1721    [ doi:10.1107/S1600536808024872 ]

3-(2-Chloro-6-fluorophenyl)-1-(2-thienyl)prop-2-en-1-one

H.-K. Fun, S. Chantrapromma, P. S. Patil and S. M. Dharmaprakash

Abstract top

The title chalcone derivative, C13H8ClFOS, crystallized as an inversion twin with two independent molecules in the asymmetric unit. The thiophene rings in both molecules are disordered over two sites: the ratios of occupancies for the major and minor components in the two molecules are 0.820 (2):0.180 (2) and 0.853 (2):0.147 (2). The dihedral angles between the major and minor components of the thiophene and benzene rings are 1.13 (18) and 2.2 (6)°, respectively, in one molecule, with corresponding values 6.09 (17) and 1.3 (6)° in the other. Weak intramolecular C-H...O and C-H...F interactions involving the prop-2-en-1-one group generate an S(5)S(5) ring motif, whereas a weak intramolecular C-H...Cl contact generates an S(6) ring motif. In the crystal structure, molecules of both the major and minor components are linked into infinite one-dimensional chains along the b axis. The crystal structure is stabilized by weak C-H...O, C-H...F, C-H...Cl and C-H...[pi] interactions.

Comment top

Chalcone derivatives have received much attention in recent years (Chopra et al., 2007). Some chalcone derivatives have been found to have nonlinear optical properties (Agrinskaya et al., 1999). As part of our research on the synthesis and characterization of chalcone derivatives (Patil et al., 2007a, b, c), we report here the structure of the title compound.

In the asymmetric unit of the title compound (Fig. 1), there are two independent molecules A and B. The enone fragment, thiophene and benzene rings are individually essentially co-planar. The thiophene rings in both molecules are disordered over two sites which correspond to a rotation of approximately 180° about the single C—C bond (C9—C10). The approximate ratios of occupancies for the major and minor components are 0.820 (2):0.180 (2) in A and 0.853 (2):0.147 (2) in B. The dihedral angles between the major and and minor components of thiophene and the benzene rings are 1.13 (18)° [S1A/C10A–C13A with C1A–C6A] and 2.2 (6)° [S1X/C10A/C11X–C13X with C1A–C6A] in A and 6.09 (17)° [S1B/C10B–C13B with C1B–C6B] and 1.3 (6)° [S1Y/C10B/C11Y–C13Y with C1B–C6B] in B. Weak intramolecular C—H···O and C—H···F interactions involving the prop-2-en-1-one moiety generate an S(5)S(5) ring motif whereas a weak intramolecular C—H···Cl interaction generates an S(6) ring motif (Bernstein et al., 1995) (Fig. 1 and Table 1). Bond lengths and angles in molecules A and B are slightly different but all are in normal ranges (Allen et al., 1987) and comparable to those in a related structure (Fun et al., 2008).

Since the thiophene rings in both molecules are disordered over two sites, there will be four discrete modes of packing in the structure involving the major and minor components. In Fig. 2 only the molecules of the two major components are shown and they are linked into chains along the b axis. The crystal is stabilized by weak C—H···O, C—H···F and C—H···Cl interactions (Table 1) and further stabilized by C—H···π interactions (Table 1); Cg1, Cg2, Cg3, Cg4, Cg5 and Cg6 are the centroids of the S1A/C10A–C13A, S1B/C10B—C13B, S1X/C10A/C11X–C13X, S1Y/C10B/C11Y–C13Y, C1A–C6A and C1B–C6B rings, respectively.

Related literature top

For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For related structures, see, for example: Fun et al. (2008); Patil et al. (2007b,c). For background to the applications of substituted chalcones, see, for example: Agrinskaya et al. (1999); Chopra et al. (2007). Patil et al. (2007a).

Experimental top

The title compound was synthesized by the condensation of 2-chloro-6-fluorobenzaldehyde (0.01 mol, 1.58 g) with 2-acetylthiophene (0.01 mol, 1.07 ml) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (5 ml, 30%). After stirring (6 h), the contents of the flask were poured into ice-cold water (500 ml) and left to stand for 5 h. The resulting crude solid was filtered and dried. Colorless single crystals of the title compound suitable for x-ray structure determination were grown by slow evaporation of an acetone solution at room temperature.

Refinement top

All H atoms were placed in calculated positions with d(C—H) = 0.93 Å, Uiso=1.2Ueq(C) for CH and aromatic. The highest residual electron density peak is located at 0.36 Å from F1B and the deepest hole is located at 0.56 Å from Cl1B. Similarity and rigid-bond restraints were applied to the disordered atoms in the thiophene rings. Even though the structure contains heavy atoms, the absolute structure cannot be acertained from the Flack parameter because of the racemic twinning of the crystal with BASF = 0.43 (7).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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, 2003).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atomic numbering. Weak intramolecular C—H···O, C—H···F and C—H···Cl interactions are drawn as dashed lines. The major disorder components are shown with the solid bonds whereas the minor disorder components are shown with open bonds.
[Figure 2] Fig. 2. The crystal packing of the major components of (I), viewed along the a axis showing that the molecules are linked in infinite one-dimensional chains approximately along the b axis. Hydrogen bonds are drawn as dashed lines.
3-(2-Chloro-6-fluorophenyl)-1-(2-thienyl)prop-2-en-1-one top
Crystal data top
C13H8ClFOSF000 = 1088
Mr = 266.71Dx = 1.568 Mg m−3
Monoclinic, CcMo Kα radiation
λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 6525 reflections
a = 12.1137 (3) Åθ = 2.3–30.0º
b = 10.5012 (3) ŵ = 0.51 mm−1
c = 18.6689 (5) ÅT = 100.0 (1) K
β = 107.882 (3)ºBlock, colorless
V = 2260.11 (11) Å30.38 × 0.27 × 0.19 mm
Z = 8
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		6525 independent reflections
Radiation source: fine-focus sealed tube5474 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.084
Detector resolution: 8.33 pixels mm-1θmax = 30.0º
T = 100.0(1) Kθmin = 2.3º
ω scansh = −17→17
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		k = −14→14
Tmin = 0.830, Tmax = 0.911l = −26→26
26405 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.063  w = 1/[σ2(Fo2) + (0.089P)2 + 4.5385P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.171(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.83 e Å−3
6525 reflectionsΔρmin = −0.91 e Å−3
347 parametersExtinction correction: none
233 restraintsAbsolute structure: Flack (1983), 3231 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.43 (7)
Secondary atom site location: difference Fourier map
Crystal data top
C13H8ClFOSV = 2260.11 (11) Å3
Mr = 266.71Z = 8
Monoclinic, CcMo Kα
a = 12.1137 (3) ŵ = 0.51 mm−1
b = 10.5012 (3) ÅT = 100.0 (1) K
c = 18.6689 (5) Å0.38 × 0.27 × 0.19 mm
β = 107.882 (3)º
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		6525 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		5474 reflections with I > 2σ(I)
Tmin = 0.830, Tmax = 0.911Rint = 0.084
26405 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.171Δρmax = 0.83 e Å−3
S = 1.05Δρmin = −0.91 e Å−3
6525 reflectionsAbsolute structure: Flack (1983), 3231 Friedel pairs
347 parametersFlack parameter: 0.43 (7)
233 restraints
Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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*/UeqOcc. (<1)
Cl1A0.16981 (8)0.06049 (9)0.04048 (5)0.0439 (2)
F1A−0.22351 (13)−0.16353 (19)−0.01215 (9)0.0282 (4)
O1A−0.23551 (18)0.1662 (2)−0.18144 (12)0.0271 (5)
C1A0.0753 (3)−0.0405 (3)0.05750 (18)0.0304 (7)
C2A0.1172 (3)−0.1253 (3)0.11799 (18)0.0368 (8)
H2AA0.1943−0.12080.14780.044*
C3A0.0444 (4)−0.2155 (3)0.1335 (2)0.0450 (9)
H3AA0.0725−0.27010.17440.054*
C4A−0.0684 (4)−0.2251 (3)0.0895 (2)0.0408 (9)
H4AA−0.1171−0.28700.09890.049*
C5A−0.1078 (3)−0.1421 (3)0.03161 (18)0.0326 (7)
C6A−0.0413 (3)−0.0465 (3)0.01129 (16)0.0248 (6)
C7A−0.0979 (3)0.0341 (3)−0.05309 (16)0.0240 (6)
H7AA−0.17640.0172−0.07520.029*
C8A−0.0570 (3)0.1277 (3)−0.08580 (17)0.0250 (6)
H8AA0.02040.1516−0.06610.030*
C9A−0.1314 (2)0.1940 (2)−0.15224 (16)0.0209 (6)
C10A−0.0801 (2)0.2973 (2)−0.18457 (15)0.0206 (5)
S1A−0.16312 (8)0.37629 (9)−0.26092 (5)0.0256 (2)0.821 (2)
C11A0.0339 (4)0.3415 (5)−0.1616 (3)0.0319 (11)0.821 (2)
H11A0.09220.3078−0.12120.038*0.821 (2)
C12A0.0509 (4)0.4447 (4)−0.2072 (2)0.0288 (9)0.821 (2)
H12A0.12060.4877−0.19970.035*0.821 (2)
C13A−0.0498 (3)0.4716 (3)−0.2634 (2)0.0244 (8)0.821 (2)
H13A−0.05570.5350−0.29920.029*0.821 (2)
S1X0.0540 (5)0.3451 (5)−0.1503 (3)0.0244 (12)*0.179 (2)
C11X−0.1495 (13)0.3737 (17)−0.2410 (11)0.035 (5)*0.179 (2)
H11B−0.23000.3692−0.25970.042*0.179 (2)
C12X−0.0788 (12)0.4597 (16)−0.2659 (9)0.020 (4)*0.179 (2)
H12B−0.10500.5093−0.30910.025*0.179 (2)
C13X0.0334 (13)0.4609 (17)−0.2182 (10)0.026 (4)*0.179 (2)
H13B0.09060.5170−0.22220.031*0.179 (2)
Cl1B−0.16932 (8)0.69186 (9)−0.16305 (5)0.0416 (2)
F1B0.22038 (13)0.9255 (2)−0.10610 (9)0.0291 (4)
O1B0.23296 (17)0.60229 (19)0.06450 (12)0.0267 (5)
C1B−0.0721 (3)0.7932 (3)−0.18114 (17)0.0250 (6)
C2B−0.1171 (3)0.8706 (4)−0.24489 (19)0.0353 (8)
H2BA−0.19300.8603−0.27580.042*
C3B−0.0460 (3)0.9621 (3)−0.2606 (2)0.0352 (7)
H3BA−0.07431.0140−0.30260.042*
C4B0.0651 (3)0.9774 (3)−0.21507 (17)0.0341 (7)
H4BA0.11271.0397−0.22540.041*
C5B0.1055 (3)0.8987 (3)−0.15358 (16)0.0248 (6)
C6B0.0415 (2)0.8020 (3)−0.13370 (16)0.0206 (5)
C7B0.0981 (2)0.7253 (2)−0.06705 (15)0.0205 (5)
H7BA0.17260.7514−0.04010.025*
C8B0.0591 (3)0.6225 (3)−0.03853 (16)0.0232 (6)
H8BA−0.01360.5885−0.06290.028*
C9B0.1334 (3)0.5649 (3)0.03181 (16)0.0229 (6)
C10B0.0835 (2)0.4603 (3)0.06389 (15)0.0195 (5)
S1B0.16576 (7)0.39734 (8)0.14734 (5)0.02200 (18)0.853 (2)
C11B0.0601 (3)0.2918 (4)0.1489 (2)0.0220 (9)0.853 (2)
H11C0.06620.23410.18770.026*0.853 (2)
C12B−0.0348 (3)0.3014 (4)0.0865 (2)0.0243 (8)0.853 (2)
H12C−0.10070.25070.07730.029*0.853 (2)
C13B−0.0199 (4)0.3982 (4)0.0380 (2)0.0222 (8)0.853 (2)
H13C−0.07550.4179−0.00740.027*0.853 (2)
S1Y−0.0509 (5)0.4042 (6)0.0261 (3)0.0182 (12)0.147 (2)
C11Y−0.0421 (15)0.293 (2)0.0931 (12)0.028 (5)*0.147 (2)
H11D−0.10160.23800.09470.034*0.147 (2)
C12Y0.0663 (16)0.295 (2)0.1448 (13)0.028 (6)*0.147 (2)
H12D0.09120.24180.18630.033*0.147 (2)
C13Y0.1343 (15)0.3903 (17)0.1263 (10)0.028 (5)*0.147 (2)
H13D0.21060.40450.15550.034*0.147 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0386 (4)0.0458 (5)0.0426 (5)−0.0123 (4)0.0056 (4)0.0065 (4)
F1A0.0116 (6)0.0517 (10)0.0204 (7)−0.0127 (7)0.0036 (6)0.0033 (7)
O1A0.0269 (9)0.0264 (9)0.0285 (10)−0.0043 (8)0.0090 (8)0.0000 (8)
C1A0.0317 (15)0.0328 (15)0.0268 (14)0.0066 (12)0.0090 (12)−0.0026 (12)
C2A0.0403 (17)0.0429 (17)0.0254 (15)0.0147 (15)0.0074 (14)−0.0034 (13)
C3A0.081 (2)0.0263 (14)0.0353 (16)0.0153 (16)0.0295 (17)0.0072 (12)
C4A0.069 (2)0.0250 (14)0.0328 (16)0.0000 (16)0.0216 (16)0.0028 (13)
C5A0.0544 (17)0.0239 (13)0.0264 (13)−0.0046 (13)0.0225 (12)−0.0031 (11)
C6A0.0343 (14)0.0207 (11)0.0227 (12)0.0018 (11)0.0138 (11)−0.0031 (9)
C7A0.0270 (12)0.0229 (12)0.0233 (12)0.0017 (11)0.0094 (10)−0.0029 (10)
C8A0.0279 (13)0.0218 (12)0.0264 (13)−0.0039 (10)0.0102 (11)0.0016 (10)
C9A0.0295 (13)0.0158 (10)0.0185 (11)0.0010 (10)0.0089 (10)−0.0008 (9)
C10A0.0254 (12)0.0199 (11)0.0193 (11)−0.0015 (10)0.0110 (10)−0.0031 (9)
S1A0.0276 (4)0.0256 (4)0.0234 (4)−0.0015 (3)0.0078 (3)0.0045 (3)
C11A0.0287 (19)0.044 (2)0.0208 (18)−0.0121 (17)0.0050 (15)−0.0007 (15)
C12A0.0340 (17)0.0274 (17)0.0274 (18)−0.0059 (15)0.0130 (14)−0.0062 (14)
C13A0.0245 (15)0.0188 (14)0.0354 (17)−0.0091 (13)0.0172 (13)−0.0001 (12)
Cl1B0.0370 (4)0.0403 (4)0.0428 (4)−0.0098 (3)0.0053 (4)0.0077 (4)
F1B0.0074 (6)0.0587 (11)0.0163 (7)−0.0102 (7)−0.0037 (5)0.0189 (7)
O1B0.0227 (9)0.0250 (9)0.0307 (10)−0.0037 (8)0.0059 (8)0.0044 (8)
C1B0.0251 (13)0.0275 (13)0.0227 (13)0.0006 (11)0.0076 (11)0.0039 (11)
C2B0.0312 (15)0.0475 (18)0.0287 (15)0.0180 (14)0.0111 (12)0.0114 (13)
C3B0.0498 (17)0.0322 (14)0.0287 (14)0.0198 (14)0.0196 (13)0.0133 (12)
C4B0.0592 (19)0.0254 (13)0.0247 (14)0.0095 (13)0.0235 (13)0.0042 (11)
C5B0.0328 (14)0.0222 (12)0.0212 (12)−0.0005 (11)0.0108 (11)−0.0018 (10)
C6B0.0231 (12)0.0189 (11)0.0222 (12)0.0012 (9)0.0108 (10)−0.0025 (9)
C7B0.0229 (11)0.0195 (11)0.0210 (12)0.0001 (10)0.0096 (10)0.0004 (9)
C8B0.0256 (13)0.0210 (12)0.0220 (12)−0.0015 (10)0.0059 (10)−0.0003 (10)
C9B0.0278 (13)0.0172 (11)0.0253 (13)−0.0019 (10)0.0108 (11)−0.0005 (10)
C10B0.0208 (11)0.0191 (11)0.0187 (11)0.0013 (10)0.0061 (9)−0.0008 (9)
S1B0.0200 (4)0.0232 (3)0.0219 (4)−0.0004 (3)0.0051 (3)0.0069 (3)
C11B0.0279 (15)0.0198 (15)0.0219 (15)0.0022 (12)0.0132 (12)0.0063 (11)
C12B0.0255 (15)0.0203 (14)0.0292 (17)−0.0052 (12)0.0117 (13)−0.0045 (12)
C13B0.0195 (16)0.0220 (15)0.0212 (16)0.0032 (13)0.0005 (13)0.0009 (12)
S1Y0.006 (2)0.029 (2)0.015 (2)−0.0037 (18)−0.0044 (16)0.0052 (18)
Geometric parameters (Å, °) top
Cl1A—C1A1.661 (4)Cl1B—C1B1.697 (3)
F1A—C5A1.407 (4)F1B—C5B1.430 (3)
O1A—C9A1.245 (3)O1B—C9B1.237 (3)
C1A—C2A1.405 (5)C1B—C6B1.392 (4)
C1A—C6A1.413 (4)C1B—C2B1.405 (4)
C2A—C3A1.385 (6)C2B—C3B1.380 (5)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.365 (6)C3B—C4B1.363 (5)
C3A—H3AA0.9300C3B—H3BA0.9300
C4A—C5A1.355 (5)C4B—C5B1.377 (4)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.410 (4)C5B—C6B1.395 (4)
C6A—C7A1.458 (4)C6B—C7B1.464 (4)
C7A—C8A1.331 (4)C7B—C8B1.351 (4)
C7A—H7AA0.9300C7B—H7BA0.9300
C8A—C9A1.466 (4)C8B—C9B1.474 (4)
C8A—H8AA0.9300C8B—H8BA0.9300
C9A—C10A1.470 (4)C9B—C10B1.467 (4)
C10A—C11X1.384 (14)C10B—C13Y1.355 (14)
C10A—C11A1.394 (5)C10B—C13B1.363 (5)
C10A—S1X1.631 (6)C10B—S1Y1.671 (6)
C10A—S1A1.688 (3)C10B—S1B1.704 (3)
S1A—C13A1.712 (4)S1B—C11B1.700 (4)
C11A—C12A1.431 (6)C11B—C12B1.366 (5)
C11A—H11A0.9300C11B—H11C0.9300
C12A—C13A1.372 (5)C12B—C13B1.409 (6)
C12A—H12A0.9300C12B—H12C0.9300
C13A—H13A0.9300C13B—H13C0.9300
S1X—C13X1.718 (14)S1Y—C11Y1.692 (16)
C11X—C12X1.418 (16)C11Y—C12Y1.369 (16)
C11X—H11B0.9300C11Y—H11D0.9300
C12X—C13X1.377 (15)C12Y—C13Y1.402 (17)
C12X—H12B0.9300C12Y—H12D0.9300
C13X—H13B0.9300C13Y—H13D0.9300
C2A—C1A—C6A120.6 (3)C6B—C1B—C2B123.5 (3)
C2A—C1A—Cl1A117.3 (3)C6B—C1B—Cl1B121.7 (2)
C6A—C1A—Cl1A122.0 (2)C2B—C1B—Cl1B114.7 (2)
C3A—C2A—C1A120.4 (3)C3B—C2B—C1B118.5 (3)
C3A—C2A—H2AA119.8C3B—C2B—H2BA120.8
C1A—C2A—H2AA119.8C1B—C2B—H2BA120.8
C4A—C3A—C2A120.5 (3)C4B—C3B—C2B120.7 (3)
C4A—C3A—H3AA119.7C4B—C3B—H3BA119.6
C2A—C3A—H3AA119.7C2B—C3B—H3BA119.6
C5A—C4A—C3A118.4 (4)C3B—C4B—C5B118.6 (3)
C5A—C4A—H4AA120.8C3B—C4B—H4BA120.7
C3A—C4A—H4AA120.8C5B—C4B—H4BA120.7
C4A—C5A—F1A113.8 (3)C4B—C5B—C6B125.1 (3)
C4A—C5A—C6A125.6 (3)C4B—C5B—F1B115.3 (3)
F1A—C5A—C6A120.5 (3)C6B—C5B—F1B119.5 (2)
C5A—C6A—C1A114.5 (3)C1B—C6B—C5B113.6 (3)
C5A—C6A—C7A118.2 (3)C1B—C6B—C7B128.1 (3)
C1A—C6A—C7A127.4 (3)C5B—C6B—C7B118.3 (2)
C8A—C7A—C6A131.3 (3)C8B—C7B—C6B130.2 (3)
C8A—C7A—H7AA114.4C8B—C7B—H7BA114.9
C6A—C7A—H7AA114.4C6B—C7B—H7BA114.9
C7A—C8A—C9A121.3 (3)C7B—C8B—C9B119.2 (3)
C7A—C8A—H8AA119.4C7B—C8B—H8BA120.4
C9A—C8A—H8AA119.4C9B—C8B—H8BA120.4
O1A—C9A—C8A122.5 (3)O1B—C9B—C10B119.8 (3)
O1A—C9A—C10A119.5 (2)O1B—C9B—C8B123.0 (3)
C8A—C9A—C10A118.0 (2)C10B—C9B—C8B117.1 (2)
C11X—C10A—C11A110.8 (7)C13Y—C10B—C13B99.8 (8)
C11X—C10A—C9A120.4 (7)C13Y—C10B—C9B128.5 (8)
C11A—C10A—C9A128.6 (3)C13B—C10B—C9B131.5 (3)
C11X—C10A—S1X114.8 (7)C13Y—C10B—S1Y107.3 (8)
C9A—C10A—S1X124.2 (3)C9B—C10B—S1Y124.2 (3)
C11A—C10A—S1A111.9 (3)C13B—C10B—S1B110.7 (3)
C9A—C10A—S1A119.5 (2)C9B—C10B—S1B117.7 (2)
S1X—C10A—S1A116.3 (3)S1Y—C10B—S1B118.0 (3)
C10A—S1A—C13A92.04 (16)C11B—S1B—C10B92.09 (15)
C10A—C11A—C12A112.2 (4)C12B—C11B—S1B112.3 (3)
C10A—C11A—H11A123.9C12B—C11B—H11C123.9
C12A—C11A—H11A123.9S1B—C11B—H11C123.9
C13A—C12A—C11A110.8 (4)C11B—C12B—C13B111.1 (3)
C13A—C12A—H12A124.6C11B—C12B—H12C124.4
C11A—C12A—H12A124.6C13B—C12B—H12C124.4
C12A—C13A—S1A112.9 (3)C10B—C13B—C12B113.8 (3)
C12A—C13A—H13A123.5C10B—C13B—H13C123.1
S1A—C13A—H13A123.5C12B—C13B—H13C123.1
C10A—S1X—C13X91.6 (6)C10B—S1Y—C11Y95.7 (6)
C10A—C11X—C12X109.3 (11)C12Y—C11Y—S1Y109.6 (13)
C10A—C11X—H11B125.3C12Y—C11Y—H11D125.2
C12X—C11X—H11B125.3S1Y—C11Y—H11D125.2
C13X—C12X—C11X111.7 (13)C11Y—C12Y—C13Y110.5 (15)
C13X—C12X—H12B124.1C11Y—C12Y—H12D124.7
C11X—C12X—H12B124.1C13Y—C12Y—H12D124.7
C12X—C13X—S1X111.1 (11)C10B—C13Y—C12Y116.8 (13)
C12X—C13X—H13B124.4C10B—C13Y—H13D121.6
S1X—C13X—H13B124.4C12Y—C13Y—H13D121.6
C6A—C1A—C2A—C3A−0.5 (5)C6B—C1B—C2B—C3B−1.5 (5)
Cl1A—C1A—C2A—C3A−177.4 (3)Cl1B—C1B—C2B—C3B175.4 (3)
C1A—C2A—C3A—C4A1.3 (5)C1B—C2B—C3B—C4B−0.2 (5)
C2A—C3A—C4A—C5A−1.7 (5)C2B—C3B—C4B—C5B0.7 (5)
C3A—C4A—C5A—F1A177.4 (3)C3B—C4B—C5B—C6B0.6 (5)
C3A—C4A—C5A—C6A1.4 (5)C3B—C4B—C5B—F1B−176.4 (3)
C4A—C5A—C6A—C1A−0.5 (5)C2B—C1B—C6B—C5B2.5 (4)
F1A—C5A—C6A—C1A−176.3 (3)Cl1B—C1B—C6B—C5B−174.2 (2)
C4A—C5A—C6A—C7A179.7 (3)C2B—C1B—C6B—C7B−178.7 (3)
F1A—C5A—C6A—C7A3.9 (4)Cl1B—C1B—C6B—C7B4.6 (4)
C2A—C1A—C6A—C5A0.1 (4)C4B—C5B—C6B—C1B−2.1 (4)
Cl1A—C1A—C6A—C5A176.8 (2)F1B—C5B—C6B—C1B174.8 (3)
C2A—C1A—C6A—C7A179.8 (3)C4B—C5B—C6B—C7B179.0 (3)
Cl1A—C1A—C6A—C7A−3.4 (5)F1B—C5B—C6B—C7B−4.1 (4)
C5A—C6A—C7A—C8A−177.9 (3)C1B—C6B—C7B—C8B5.9 (5)
C1A—C6A—C7A—C8A2.3 (5)C5B—C6B—C7B—C8B−175.4 (3)
C6A—C7A—C8A—C9A178.5 (3)C6B—C7B—C8B—C9B−178.0 (3)
C7A—C8A—C9A—O1A−0.3 (4)C7B—C8B—C9B—O1B−3.7 (4)
C7A—C8A—C9A—C10A179.3 (3)C7B—C8B—C9B—C10B175.0 (3)
O1A—C9A—C10A—C11X8.0 (11)O1B—C9B—C10B—C13Y−3.0 (13)
C8A—C9A—C10A—C11X−171.6 (11)C8B—C9B—C10B—C13Y178.2 (12)
O1A—C9A—C10A—C11A−178.8 (4)O1B—C9B—C10B—C13B−176.5 (4)
C8A—C9A—C10A—C11A1.6 (5)C8B—C9B—C10B—C13B4.7 (5)
O1A—C9A—C10A—S1X178.4 (3)O1B—C9B—C10B—S1Y178.4 (4)
C8A—C9A—C10A—S1X−1.2 (4)C8B—C9B—C10B—S1Y−0.4 (5)
O1A—C9A—C10A—S1A−0.2 (4)O1B—C9B—C10B—S1B1.6 (4)
C8A—C9A—C10A—S1A−179.8 (2)C8B—C9B—C10B—S1B−177.1 (2)
C11X—C10A—S1A—C13A81 (5)C13Y—C10B—S1B—C11B−19 (5)
C11A—C10A—S1A—C13A−1.0 (3)C13B—C10B—S1B—C11B−1.8 (3)
C9A—C10A—S1A—C13A−179.7 (2)C9B—C10B—S1B—C11B179.7 (3)
S1X—C10A—S1A—C13A1.6 (3)S1Y—C10B—S1B—C11B2.7 (3)
C11X—C10A—C11A—C12A−6.0 (11)C10B—S1B—C11B—C12B1.5 (3)
C9A—C10A—C11A—C12A−179.8 (3)S1B—C11B—C12B—C13B−0.9 (5)
S1X—C10A—C11A—C12A−151 (5)C13Y—C10B—C13B—C12B5.0 (11)
S1A—C10A—C11A—C12A1.6 (5)C9B—C10B—C13B—C12B179.9 (3)
C10A—C11A—C12A—C13A−1.5 (6)S1Y—C10B—C13B—C12B−150 (3)
C11A—C12A—C13A—S1A0.8 (5)S1B—C10B—C13B—C12B1.6 (4)
C10A—S1A—C13A—C12A0.1 (3)C11B—C12B—C13B—C10B−0.5 (5)
C11X—C10A—S1X—C13X−7.8 (13)C13Y—C10B—S1Y—C11Y1.6 (14)
C11A—C10A—S1X—C13X29 (4)C13B—C10B—S1Y—C11Y28 (2)
C9A—C10A—S1X—C13X−178.6 (8)C9B—C10B—S1Y—C11Y−179.5 (10)
S1A—C10A—S1X—C13X0.0 (8)S1B—C10B—S1Y—C11Y−2.8 (10)
C11A—C10A—C11X—C12X9.6 (18)C10B—S1Y—C11Y—C12Y−1(2)
C9A—C10A—C11X—C12X−176.1 (11)S1Y—C11Y—C12Y—C13Y1(3)
S1X—C10A—C11X—C12X12.7 (19)C13B—C10B—C13Y—C12Y−5(2)
S1A—C10A—C11X—C12X−91 (6)C9B—C10B—C13Y—C12Y179.7 (16)
C10A—C11X—C12X—C13X−12 (2)S1Y—C10B—C13Y—C12Y−1(2)
C11X—C12X—C13X—S1X7(2)S1B—C10B—C13Y—C12Y159 (6)
C10A—S1X—C13X—C12X0.4 (16)C11Y—C12Y—C13Y—C10B0(3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C7A—H7AA···F1A0.932.392.814 (4)107
C7A—H7AA···O1A0.932.452.827 (4)104
C8A—H8AA···Cl1A0.932.443.103 (3)129
C7B—H7BA···F1B0.932.372.794 (3)107
C7B—H7BA···O1B0.932.432.812 (3)104
C8B—H8BA···Cl1B0.932.463.105 (3)126
C11A—H11A···F1Ai0.932.543.375 (6)150
C12A—H12A···O1Ai0.932.513.402 (5)161
C12B—H12C···O1Bii0.932.503.427 (4)174
C3A—H3AA···Cg1iii0.933.063.748 (4)132
C3A—H3AA···Cg3iii0.933.143.825 (7)132
C3B—H3BA···Cg5iv0.933.023.778 (4)140
C11B—H11C···Cg6v0.932.813.677 (4)155
C13A—H13A···Cg2iv0.932.823.608 (4)143
C13A—H13A···Cg4iv0.932.823.625 (8)145
C12X—H12B···Cg2iv0.933.213.835 (16)126
C12X—H12B···Cg4iv0.933.183.840 (18)129
C12Y—H12D···Cg6v0.933.043.79 (2)139
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x−1/2, y−1/2, z; (iii) x, −y, z+1/2; (iv) x, −y+1, z−1/2; (v) x, −y+1, z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C7A—H7AA···F1A0.932.392.814 (4)107
C7A—H7AA···O1A0.932.452.827 (4)104
C8A—H8AA···Cl1A0.932.443.103 (3)129
C7B—H7BA···F1B0.932.372.794 (3)107
C7B—H7BA···O1B0.932.432.812 (3)104
C8B—H8BA···Cl1B0.932.463.105 (3)126
C11A—H11A···F1Ai0.932.543.375 (6)150
C12A—H12A···O1Ai0.932.513.402 (5)161
C12B—H12C···O1Bii0.932.503.427 (4)174
C3A—H3AA···Cg1iii0.933.063.748 (4)132
C3A—H3AA···Cg3iii0.933.143.825 (7)132
C3B—H3BA···Cg5iv0.933.023.778 (4)140
C11B—H11C···Cg6v0.932.813.677 (4)155
C13A—H13A···Cg2iv0.932.823.608 (4)143
C13A—H13A···Cg4iv0.932.823.625 (8)145
C12X—H12B···Cg2iv0.933.213.835 (16)126
C12X—H12B···Cg4iv0.933.183.840 (18)129
C12Y—H12D···Cg6v0.933.043.79 (2)139
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x−1/2, y−1/2, z; (iii) x, −y, z+1/2; (iv) x, −y+1, z−1/2; (v) x, −y+1, z+1/2.
Acknowledgements top

This work is supported by Department of Science and Technology (DST), Government of India, under grant No. SR/S2/LOP-17/2006. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

references
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