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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 4| April 2012| Page o1163
doi:10.1107/S1600536812011841

(2E)-1-(2,6-Di­chloro-3-fluoro­phen­yl)-3-(4-meth­­oxy­phen­yl)prop-2-en-1-one

A. S. Praveen,a Jerry P. Jasinski,b* James A. Golen,b H. S. Yathirajana and B. Narayanac

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, 574 199, India
*Correspondence e-mail: jjasinski@keene.edu

(Received 12 March 2012; accepted 19 March 2012; online 24 March 2012)

There are two independent mol­ecules in the asymmetric unit of the title compound, C16H11Cl2FO2. The F atom equally populates both meta positions of the 6-dichloro-3-fluoro­phenyl ring in each mol­ecule, resulting in 0.5 occupancy for both the F and H atoms in these positions. The dihedral angle between the mean planes of the benzene rings are 77.5 (2) and 89.8 (8)°in the two mol­ecules. In the crystal, weak C—H⋯F and C—H⋯O inter­actions involving the half-occupied H and F atoms are observed. Weak π–π stacking inter­actions [centroid—centroid distance = 3.150 (2) Å] also contribute to the crystal stability.

Related literature

For the pharmacological importance of chalcones, see: Dominguez et al. (2001[Dominguez, J. N., Charris, J. E., Lobo, G., de Dominguez, N. G., Moreno, M. M., Riggione, F., Sanchez, E., Olson, J. & Rosenthal, P. J. (2001). Eur. J. Med. Chem. 36, 555-560.]); Li et al. (1995[Li, R., Chen, X., Gong, B., Dominguez, J. N., Davidson, E., Kurzban, G., Miller, R. E., Nuzum, E. O. & Rosenthal, P. J. (1995). J. Med. Chem. 38, 5031-5037.]); Mei et al. (2001[Mei, L., Prapon, W. & Mei, L. G. (2001). J. Med. Chem. 44, 4443-4452.]); Sarojini et al. (2006[Sarojini, B. K., Narayana, B., Ashalatha, B. V., Indira, J. & Lobo, K. G. (2006). J. Cryst. Growth, 295, 54-59.]). For related structures, see: Betz et al. (2012[Betz, R., Gerber, T., Hosten, E., Praveen, A. S., Yathirajan, H. S. & Narayana, B. (2012). Acta Cryst. E68, o512.]); Yathirajan et al. (2007[Yathirajan, H. S., Mayekar, A. N., Narayana, B., Sarojini & Bolte, M. (2007). Acta Cryst. E63, o428-o429.]). For standard bond lengths, 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

  • C16H11Cl2FO2

  • Mr = 325.15

  • Monoclinic, P 21 /c

  • a = 11.9035 (6) Å

  • b = 10.4472 (5) Å

  • c = 23.7435 (12) Å

  • β = 92.296 (4)°

  • V = 2950.3 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.45 mm−1

  • T = 173 K

  • 0.24 × 0.20 × 0.17 mm
Data collection

  • Oxford Diffraction Xcalibur Eos Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.900, Tmax = 0.927

  • 15257 measured reflections

  • 7015 independent reflections

  • 5165 reflections with I > 2σ(I)

  • Rint = 0.023
Refinement

  • R[F2 > 2σ(F2)] = 0.061

  • wR(F2) = 0.145

  • S = 1.06

  • 7015 reflections

  • 401 parameters

  • 4 restraints

  • H-atom parameters constrained

  • Δρmax = 0.67 e Å−3

  • Δρmin = −0.57 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C2—H2A⋯F1Ai 0.95 2.79 3.657 (7) 153
C4—H4A⋯F1ii 0.95 2.75 3.410 (5) 127
C11—H11A⋯O3ii 0.95 2.56 3.451 (3) 156
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812011841/bt5846sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812011841/bt5846Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812011841/bt5846Isup3.cml

checkCIF report


Comment top

Many Chalcones are known to exhibit various biological properties such as antimalarial (Li et al., 1995), antifungal (Dominguez et al., 2001) and antibacterial activity (Mei et al., 2001). They are also finding application as organic nonlinear optical materials (NLO) for their SHG conversion efficiency (Sarojini et al., 2006). Crystal structures of some related chalcones, viz., (2E)-1-(2,4-dichlorophenyl)-3-(2-hydroxy-3-methoxyphenyl)prop-2-en-1-one (Yathirajan et al., 2007) and (2E)-1-(2,6-dichloro-3-fluorophenyl)-3-(4-fluorophenyl)prop-2-en-1-one (Betz et al., 2012) have been reported. As part of our ongoing studies on chalcones, the title compound (I), C16H11Cl2FO2, was synthesized and its crystal structure is reported.

In (I) two molecules crystallize in the asymmetric unit (Fig. 1). In the 2,6-dichloro-3-fluorophenyl ring, the fluorine atom equally populates both meta positions of the phenyl ring in each molecule (C2 & C4; C18 & C20) resulting in 0.5 occupancy for both the fluorine and hydrogen atoms (H2A & H4A; H18A & H20A) in these positions. The dihedral angle between the mean planes of the benzene rings in each molecule is 77.5 (2)° and 89.8 (8)°, respectively. Bond lengths are in normal ranges (Allen et al., 1987). Crystal packing is enhanced by weak C—H···F and C—H···O intermolecular interactions (Table 1) from both half-occupied H and F atoms supporting parallel chains along the b axis (Fig. 2) aa well as weak π–π stacking interactions (Table 2).

Related literature top

For the pharmacological importance of chalcones, see: Dominguez et al. (2001); Li et al. (1995); Mei et al. (2001); Sarojini et al. (2006). For related structures, see: Betz et al. (2012); Yathirajan et al. (2007). For standard bond lengths, see: Allen et al. (1987).

Experimental top

To a stirred solution of 1-(2,6-dichloro-3-fluorophenyl)ethanone (1 g, 4.8 mmol) and 4-methoxybenzaldehyde (0.65 g, 4.8 mmol) in ethanol (10 ml), powdered KOH (0.40 g, 7.2 mmol) was added at 273 K. The reaction mixture was stirred at room temperature for 3 h. After completion of the reaction, the reaction mixture was poured to ice cold water and acidified with 1.5 N HCl (pH 3). The solid precipitated was filtered and dried to afford 1.4 g of the title compound, (I,) in 89% yield. X-ray quality crystals were obtained by slow evaporation of a tetrahydrofuran solution (m.p.: 361–362 K).

Refinement top

All of the H atoms were placed in their calculated positions and refined using the riding model with C—H lengths of 0.95 Å (CH) or 0.98 Å (CH3). The isotropic displacement parameters for these atoms were set from 1.19 to 1.20 (CH), or 1.49 (CH3) times Ueq of the parent atom. Overlapping of the F atoms in the meta position of the phenyl ring in each molecule resulted in H2A, H4A, H18A, H20A and F1, F1A, F2, F2A being refined at 0.50 occupancy. C2—F1 and C4—F1A bond distances were fixed at 1.33 (2) Å, C18—F2 and C20—F2A bond distances were fixed at 1.33 (06) Å.

Structure description top

Many Chalcones are known to exhibit various biological properties such as antimalarial (Li et al., 1995), antifungal (Dominguez et al., 2001) and antibacterial activity (Mei et al., 2001). They are also finding application as organic nonlinear optical materials (NLO) for their SHG conversion efficiency (Sarojini et al., 2006). Crystal structures of some related chalcones, viz., (2E)-1-(2,4-dichlorophenyl)-3-(2-hydroxy-3-methoxyphenyl)prop-2-en-1-one (Yathirajan et al., 2007) and (2E)-1-(2,6-dichloro-3-fluorophenyl)-3-(4-fluorophenyl)prop-2-en-1-one (Betz et al., 2012) have been reported. As part of our ongoing studies on chalcones, the title compound (I), C16H11Cl2FO2, was synthesized and its crystal structure is reported.

In (I) two molecules crystallize in the asymmetric unit (Fig. 1). In the 2,6-dichloro-3-fluorophenyl ring, the fluorine atom equally populates both meta positions of the phenyl ring in each molecule (C2 & C4; C18 & C20) resulting in 0.5 occupancy for both the fluorine and hydrogen atoms (H2A & H4A; H18A & H20A) in these positions. The dihedral angle between the mean planes of the benzene rings in each molecule is 77.5 (2)° and 89.8 (8)°, respectively. Bond lengths are in normal ranges (Allen et al., 1987). Crystal packing is enhanced by weak C—H···F and C—H···O intermolecular interactions (Table 1) from both half-occupied H and F atoms supporting parallel chains along the b axis (Fig. 2) aa well as weak π–π stacking interactions (Table 2).

For the pharmacological importance of chalcones, see: Dominguez et al. (2001); Li et al. (1995); Mei et al. (2001); Sarojini et al. (2006). For related structures, see: Betz et al. (2012); Yathirajan et al. (2007). For standard bond lengths, see: Allen et al. (1987).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing the atom labeling scheme and 50% probability displacement ellipsoids for two molecules in the asymmetric unit.
[Figure 2] Fig. 2. Packing diagram of the title compound viewed along the a axis.
(2E)-1-(2,6-Dichloro-3-fluorophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one top
Crystal data top
C16H11Cl2FO2F(000) = 1328
Mr = 325.15Dx = 1.464 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3879 reflections
a = 11.9035 (6) Åθ = 3.1–30.0°
b = 10.4472 (5) ŵ = 0.45 mm−1
c = 23.7435 (12) ÅT = 173 K
β = 92.296 (4)°Block, colorless
V = 2950.3 (3) Å30.24 × 0.20 × 0.17 mm
Z = 8
Data collection top
Oxford Diffraction Xcalibur Eos Gemini
diffractometer		7015 independent reflections
Radiation source: Enhance (Mo) X-ray Source5165 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 16.1500 pixels mm-1θmax = 27.9°, θmin = 3.1°
ω scansh = −10→15
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2010)		k = −13→10
Tmin = 0.900, Tmax = 0.927l = −30→31
15257 measured reflections
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.042P)2 + 3.2887P]
where P = (Fo2 + 2Fc2)/3
7015 reflections(Δ/σ)max < 0.001
401 parametersΔρmax = 0.67 e Å−3
4 restraintsΔρmin = −0.57 e Å−3
Crystal data top
C16H11Cl2FO2V = 2950.3 (3) Å3
Mr = 325.15Z = 8
Monoclinic, P21/cMo Kα radiation
a = 11.9035 (6) ŵ = 0.45 mm−1
b = 10.4472 (5) ÅT = 173 K
c = 23.7435 (12) Å0.24 × 0.20 × 0.17 mm
β = 92.296 (4)°
Data collection top
Oxford Diffraction Xcalibur Eos Gemini
diffractometer		7015 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2010)		5165 reflections with I > 2σ(I)
Tmin = 0.900, Tmax = 0.927Rint = 0.023
15257 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0614 restraints
wR(F2) = 0.145H-atom parameters constrained
S = 1.06Δρmax = 0.67 e Å−3
7015 reflectionsΔρmin = −0.57 e Å−3
401 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*/UeqOcc. (<1)
Cl10.73833 (6)0.53784 (8)0.11864 (4)0.0566 (2)
Cl20.73589 (8)0.86623 (10)0.29381 (4)0.0697 (3)
Cl30.75952 (8)0.51754 (10)0.41195 (6)0.0931 (4)
Cl40.75948 (8)0.21696 (11)0.22698 (4)0.0719 (3)
F10.5430 (3)0.4344 (3)0.16850 (18)0.0600 (10)0.50
F1A0.5483 (5)0.7210 (7)0.3246 (2)0.121 (2)0.50
F20.9551 (3)0.6350 (3)0.3500 (2)0.0771 (13)0.50
F2A0.9515 (4)0.3907 (7)0.2061 (2)0.118 (2)0.50
O10.91972 (15)0.72821 (19)0.18987 (9)0.0473 (5)
O20.57619 (15)1.3317 (2)−0.00869 (9)0.0499 (5)
O30.57623 (15)0.3266 (2)0.33521 (10)0.0514 (5)
O41.00724 (16)−0.28448 (19)0.48786 (9)0.0499 (5)
C10.6802 (2)0.5932 (3)0.17975 (13)0.0418 (6)
C20.5874 (2)0.5310 (3)0.20029 (16)0.0554 (8)
H2A0.55570.46010.18040.066*0.50
C30.5411 (3)0.5714 (3)0.24921 (17)0.0611 (9)
H3A0.47760.52870.26340.073*
C40.5875 (3)0.6741 (4)0.27727 (14)0.0570 (9)
H4A0.55640.70180.31140.068*0.50
C50.6787 (2)0.7381 (3)0.25700 (12)0.0451 (7)
C60.7264 (2)0.6993 (2)0.20724 (11)0.0355 (5)
C70.8245 (2)0.7701 (2)0.18319 (11)0.0361 (6)
C80.8000 (2)0.8855 (2)0.15059 (11)0.0360 (5)
H8A0.86140.93770.14050.043*
C90.6966 (2)0.9225 (2)0.13400 (11)0.0357 (6)
H9A0.63620.87330.14750.043*
C100.6665 (2)1.0297 (2)0.09763 (11)0.0345 (5)
C110.5534 (2)1.0535 (3)0.08407 (13)0.0447 (7)
H11A0.49791.00020.09970.054*
C120.5196 (2)1.1523 (3)0.04865 (13)0.0470 (7)
H12A0.44201.16630.04000.056*
C130.5993 (2)1.2302 (3)0.02593 (12)0.0376 (6)
C140.7130 (2)1.2079 (3)0.03816 (12)0.0402 (6)
H14A0.76801.26070.02190.048*
C150.7457 (2)1.1101 (3)0.07347 (12)0.0386 (6)
H15A0.82351.09640.08180.046*
C160.4637 (3)1.3482 (3)−0.02947 (16)0.0602 (9)
H16A0.45961.4221−0.05490.090*
H16B0.41481.36280.00220.090*
H16C0.43901.2712−0.05000.090*
C170.8124 (3)0.4772 (3)0.34698 (17)0.0618 (9)
C180.9025 (3)0.5439 (3)0.3250 (3)0.0935 (18)
H18A0.93270.61500.34540.112*0.50
C190.9488 (3)0.5117 (5)0.2757 (3)0.104 (2)
H19A1.01130.55620.26160.125*
C200.9013 (3)0.4145 (4)0.2488 (2)0.0862 (15)
H20A0.93190.39140.21390.103*0.50
C210.8131 (2)0.3439 (3)0.26580 (15)0.0562 (9)
C220.7669 (2)0.3748 (3)0.31718 (14)0.0465 (7)
C230.6745 (2)0.2949 (3)0.34163 (12)0.0406 (6)
C240.7103 (2)0.1816 (3)0.37319 (12)0.0400 (6)
H24A0.65460.13100.39020.048*
C250.8174 (2)0.1453 (2)0.37936 (11)0.0360 (6)
H25A0.87090.19790.36170.043*
C260.86199 (19)0.0345 (2)0.40993 (11)0.0328 (5)
C270.9691 (2)−0.0094 (3)0.39798 (11)0.0367 (6)
H27A1.01170.03530.37130.044*
C281.0141 (2)−0.1161 (3)0.42405 (12)0.0418 (6)
H28A1.0864−0.14580.41460.050*
C290.9545 (2)−0.1804 (2)0.46389 (11)0.0356 (5)
C300.8491 (2)−0.1371 (3)0.47756 (12)0.0404 (6)
H30A0.8083−0.18010.50550.049*
C310.8035 (2)−0.0312 (3)0.45043 (12)0.0396 (6)
H31A0.7307−0.00260.45960.048*
C320.9572 (3)−0.3425 (3)0.53478 (13)0.0508 (7)
H32A1.0056−0.41180.54940.076*
H32B0.8835−0.37730.52300.076*
H32C0.9479−0.27830.56440.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0398 (4)0.0599 (5)0.0693 (5)0.0048 (3)−0.0089 (3)−0.0187 (4)
Cl20.0707 (6)0.0786 (6)0.0601 (5)−0.0014 (5)0.0070 (4)−0.0206 (5)
Cl30.0633 (6)0.0740 (6)0.1389 (10)0.0131 (5)−0.0371 (6)−0.0454 (7)
Cl40.0612 (5)0.0891 (7)0.0663 (6)0.0046 (5)0.0130 (4)0.0001 (5)
F10.0344 (17)0.0391 (17)0.106 (3)−0.0165 (14)−0.0007 (17)−0.0054 (19)
F1A0.111 (4)0.154 (6)0.102 (4)0.008 (4)0.048 (3)0.035 (4)
F20.061 (2)0.0393 (19)0.129 (4)−0.0120 (18)−0.026 (2)−0.012 (2)
F2A0.077 (3)0.191 (7)0.086 (4)0.000 (4)0.016 (3)0.056 (4)
O10.0286 (9)0.0475 (11)0.0655 (13)0.0027 (8)−0.0018 (8)0.0070 (10)
O20.0358 (10)0.0515 (12)0.0622 (13)0.0030 (9)−0.0004 (9)0.0201 (10)
O30.0288 (9)0.0486 (11)0.0764 (15)0.0101 (9)−0.0027 (9)−0.0001 (11)
O40.0418 (10)0.0481 (11)0.0606 (13)0.0136 (9)0.0100 (9)0.0170 (10)
C10.0287 (12)0.0377 (14)0.0585 (18)0.0052 (11)−0.0052 (11)0.0057 (13)
C20.0306 (14)0.0423 (16)0.093 (3)−0.0017 (12)−0.0051 (15)0.0131 (17)
C30.0391 (16)0.056 (2)0.089 (3)0.0004 (15)0.0112 (16)0.0328 (19)
C40.0467 (17)0.070 (2)0.0554 (19)0.0143 (16)0.0148 (14)0.0232 (17)
C50.0413 (15)0.0473 (16)0.0468 (16)0.0065 (13)−0.0002 (12)0.0086 (13)
C60.0270 (12)0.0346 (13)0.0445 (14)0.0044 (10)−0.0036 (10)0.0077 (11)
C70.0307 (12)0.0364 (13)0.0410 (14)−0.0006 (10)−0.0006 (10)−0.0016 (11)
C80.0323 (12)0.0354 (13)0.0402 (14)−0.0037 (10)0.0011 (10)0.0012 (11)
C90.0312 (12)0.0336 (13)0.0424 (14)−0.0019 (10)0.0034 (10)0.0000 (11)
C100.0287 (11)0.0339 (13)0.0409 (14)−0.0003 (10)0.0013 (10)0.0003 (11)
C110.0280 (12)0.0464 (15)0.0602 (18)−0.0030 (11)0.0065 (12)0.0119 (14)
C120.0273 (12)0.0516 (17)0.0621 (19)0.0025 (12)0.0019 (12)0.0139 (15)
C130.0318 (12)0.0367 (13)0.0442 (15)0.0015 (11)−0.0005 (10)0.0028 (12)
C140.0308 (12)0.0400 (14)0.0499 (16)−0.0041 (11)0.0027 (11)0.0063 (12)
C150.0274 (12)0.0395 (14)0.0486 (15)−0.0014 (11)−0.0029 (10)0.0029 (12)
C160.0421 (16)0.059 (2)0.078 (2)0.0068 (15)−0.0109 (15)0.0170 (18)
C170.0412 (16)0.0400 (16)0.102 (3)0.0077 (13)−0.0227 (17)0.0070 (17)
C180.048 (2)0.050 (2)0.178 (5)−0.0162 (18)−0.052 (3)0.047 (3)
C190.041 (2)0.103 (4)0.166 (5)−0.017 (2)−0.022 (3)0.098 (4)
C200.0372 (18)0.099 (3)0.121 (4)−0.001 (2)−0.007 (2)0.073 (3)
C210.0315 (14)0.0593 (19)0.078 (2)0.0049 (13)−0.0020 (14)0.0289 (18)
C220.0287 (13)0.0353 (14)0.075 (2)0.0052 (11)−0.0088 (13)0.0157 (14)
C230.0303 (13)0.0363 (14)0.0549 (17)0.0047 (11)−0.0011 (11)−0.0043 (13)
C240.0309 (12)0.0375 (13)0.0518 (16)0.0017 (11)0.0052 (11)0.0027 (12)
C250.0317 (12)0.0324 (12)0.0440 (15)0.0010 (10)0.0020 (10)−0.0013 (11)
C260.0286 (11)0.0312 (12)0.0384 (14)0.0008 (10)−0.0013 (10)−0.0047 (11)
C270.0290 (12)0.0388 (13)0.0425 (14)0.0020 (10)0.0054 (10)0.0031 (12)
C280.0287 (12)0.0472 (15)0.0498 (16)0.0081 (11)0.0069 (11)0.0037 (13)
C290.0326 (12)0.0328 (12)0.0412 (14)0.0046 (10)−0.0009 (10)0.0014 (11)
C300.0361 (13)0.0418 (14)0.0439 (15)0.0021 (12)0.0094 (11)0.0047 (12)
C310.0298 (12)0.0402 (14)0.0496 (16)0.0057 (11)0.0096 (11)0.0015 (12)
C320.0507 (17)0.0482 (17)0.0536 (18)0.0037 (14)0.0040 (14)0.0162 (14)
Geometric parameters (Å, º) top
Cl1—C11.732 (3)C14—H14A0.9500
Cl2—C51.724 (3)C15—H15A0.9500
Cl3—C171.741 (4)C16—H16A0.9800
Cl4—C211.723 (4)C16—H16B0.9800
O1—C71.220 (3)C16—H16C0.9800
O2—C131.363 (3)C17—C221.381 (4)
O2—C161.419 (3)C17—C181.398 (6)
O3—C231.219 (3)C18—C191.354 (7)
O4—C291.369 (3)C18—H18A0.9500
O4—C321.420 (3)C19—C201.315 (7)
C1—C21.387 (4)C19—H19A0.9500
C1—C61.388 (4)C20—C211.359 (5)
C2—C31.372 (5)C20—H20A0.9500
C2—H2A0.9500C21—C221.396 (5)
C3—C41.368 (5)C22—C231.516 (4)
C3—H3A0.9500C23—C241.456 (4)
C4—C51.378 (4)C24—C251.333 (3)
C4—H4A0.9500C24—H24A0.9500
C5—C61.391 (4)C25—C261.455 (3)
C6—C71.514 (3)C25—H25A0.9500
C7—C81.456 (4)C26—C311.391 (4)
C8—C91.335 (3)C26—C271.395 (3)
C8—H8A0.9500C27—C281.373 (4)
C9—C101.450 (4)C27—H27A0.9500
C9—H9A0.9500C28—C291.379 (4)
C10—C111.393 (3)C28—H28A0.9500
C10—C151.403 (3)C29—C301.384 (3)
C11—C121.381 (4)C30—C311.381 (4)
C11—H11A0.9500C30—H30A0.9500
C12—C131.376 (4)C31—H31A0.9500
C12—H12A0.9500C32—H32A0.9800
C13—C141.393 (3)C32—H32B0.9800
C14—C151.368 (4)C32—H32C0.9800
C13—O2—C16118.0 (2)H16B—C16—H16C109.5
C29—O4—C32117.7 (2)C22—C17—C18119.0 (4)
C2—C1—C6120.9 (3)C22—C17—Cl3119.5 (3)
C2—C1—Cl1119.3 (2)C18—C17—Cl3121.4 (3)
C6—C1—Cl1119.8 (2)C19—C18—C17122.9 (4)
C3—C2—C1120.5 (3)C19—C18—H18A118.5
C3—C2—H2A119.8C17—C18—H18A118.5
C1—C2—H2A119.8C20—C19—C18115.5 (4)
C4—C3—C2119.0 (3)C20—C19—H19A122.3
C4—C3—H3A120.5C18—C19—H19A122.3
C2—C3—H3A120.5C19—C20—C21126.7 (5)
C3—C4—C5121.3 (3)C19—C20—H20A116.7
C3—C4—H4A119.3C21—C20—H20A116.7
C5—C4—H4A119.3C20—C21—C22118.0 (4)
C4—C5—C6120.6 (3)C20—C21—Cl4122.2 (3)
C4—C5—Cl2120.0 (3)C22—C21—Cl4119.7 (2)
C6—C5—Cl2119.4 (2)C17—C22—C21117.9 (3)
C1—C6—C5117.7 (2)C17—C22—C23120.4 (3)
C1—C6—C7120.6 (2)C21—C22—C23121.6 (3)
C5—C6—C7121.7 (2)O3—C23—C24123.1 (3)
O1—C7—C8122.1 (2)O3—C23—C22120.6 (2)
O1—C7—C6120.2 (2)C24—C23—C22116.3 (2)
C8—C7—C6117.7 (2)C25—C24—C23123.2 (3)
C9—C8—C7124.0 (2)C25—C24—H24A118.4
C9—C8—H8A118.0C23—C24—H24A118.4
C7—C8—H8A118.0C24—C25—C26127.5 (2)
C8—C9—C10127.0 (2)C24—C25—H25A116.2
C8—C9—H9A116.5C26—C25—H25A116.2
C10—C9—H9A116.5C31—C26—C27117.7 (2)
C11—C10—C15117.2 (2)C31—C26—C25123.7 (2)
C11—C10—C9119.3 (2)C27—C26—C25118.6 (2)
C15—C10—C9123.5 (2)C28—C27—C26121.2 (2)
C12—C11—C10122.0 (2)C28—C27—H27A119.4
C12—C11—H11A119.0C26—C27—H27A119.4
C10—C11—H11A119.0C27—C28—C29120.1 (2)
C13—C12—C11119.5 (2)C27—C28—H28A119.9
C13—C12—H12A120.3C29—C28—H28A119.9
C11—C12—H12A120.3O4—C29—C28115.6 (2)
O2—C13—C12124.8 (2)O4—C29—C30124.6 (2)
O2—C13—C14115.3 (2)C28—C29—C30119.9 (2)
C12—C13—C14119.9 (2)C31—C30—C29119.7 (2)
C15—C14—C13120.2 (2)C31—C30—H30A120.2
C15—C14—H14A119.9C29—C30—H30A120.2
C13—C14—H14A119.9C30—C31—C26121.3 (2)
C14—C15—C10121.2 (2)C30—C31—H31A119.3
C14—C15—H15A119.4C26—C31—H31A119.3
C10—C15—H15A119.4O4—C32—H32A109.5
O2—C16—H16A109.5O4—C32—H32B109.5
O2—C16—H16B109.5H32A—C32—H32B109.5
H16A—C16—H16B109.5O4—C32—H32C109.5
O2—C16—H16C109.5H32A—C32—H32C109.5
H16A—C16—H16C109.5H32B—C32—H32C109.5
C6—C1—C2—C3−1.8 (4)C22—C17—C18—C19−0.9 (5)
Cl1—C1—C2—C3178.8 (2)Cl3—C17—C18—C19177.1 (3)
C1—C2—C3—C40.2 (5)C17—C18—C19—C201.7 (6)
C2—C3—C4—C50.8 (5)C18—C19—C20—C21−1.0 (6)
C3—C4—C5—C6−0.3 (4)C19—C20—C21—C22−0.5 (5)
C3—C4—C5—Cl2−179.4 (2)C19—C20—C21—Cl4−179.1 (3)
C2—C1—C6—C52.2 (4)C18—C17—C22—C21−0.7 (4)
Cl1—C1—C6—C5−178.3 (2)Cl3—C17—C22—C21−178.7 (2)
C2—C1—C6—C7−177.3 (2)C18—C17—C22—C23175.9 (3)
Cl1—C1—C6—C72.2 (3)Cl3—C17—C22—C23−2.2 (4)
C4—C5—C6—C1−1.2 (4)C20—C21—C22—C171.3 (4)
Cl2—C5—C6—C1177.96 (19)Cl4—C21—C22—C17180.0 (2)
C4—C5—C6—C7178.3 (3)C20—C21—C22—C23−175.1 (3)
Cl2—C5—C6—C7−2.5 (3)Cl4—C21—C22—C233.5 (4)
C1—C6—C7—O1−79.7 (3)C17—C22—C23—O386.1 (4)
C5—C6—C7—O1100.9 (3)C21—C22—C23—O3−97.5 (3)
C1—C6—C7—C898.1 (3)C17—C22—C23—C24−93.0 (3)
C5—C6—C7—C8−81.3 (3)C21—C22—C23—C2483.4 (3)
O1—C7—C8—C9167.9 (3)O3—C23—C24—C25178.7 (3)
C6—C7—C8—C9−9.8 (4)C22—C23—C24—C25−2.2 (4)
C7—C8—C9—C10−174.4 (2)C23—C24—C25—C26179.9 (3)
C8—C9—C10—C11179.2 (3)C24—C25—C26—C31−18.7 (4)
C8—C9—C10—C151.2 (4)C24—C25—C26—C27160.9 (3)
C15—C10—C11—C12−0.4 (4)C31—C26—C27—C281.8 (4)
C9—C10—C11—C12−178.5 (3)C25—C26—C27—C28−177.7 (2)
C10—C11—C12—C13−0.1 (5)C26—C27—C28—C29−1.6 (4)
C16—O2—C13—C12−9.4 (4)C32—O4—C29—C28170.9 (3)
C16—O2—C13—C14170.9 (3)C32—O4—C29—C30−8.3 (4)
C11—C12—C13—O2−178.8 (3)C27—C28—C29—O4−179.2 (2)
C11—C12—C13—C140.9 (5)C27—C28—C29—C300.0 (4)
O2—C13—C14—C15178.6 (3)O4—C29—C30—C31−179.7 (3)
C12—C13—C14—C15−1.1 (4)C28—C29—C30—C311.2 (4)
C13—C14—C15—C100.6 (4)C29—C30—C31—C26−0.8 (4)
C11—C10—C15—C140.1 (4)C27—C26—C31—C30−0.6 (4)
C9—C10—C15—C14178.2 (3)C25—C26—C31—C30178.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···F1Ai0.952.793.657 (7)153
C4—H4A···F1ii0.952.753.410 (5)127
C11—H11A···O3ii0.952.563.451 (3)156
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC16H11Cl2FO2
Mr325.15
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)11.9035 (6), 10.4472 (5), 23.7435 (12)
β (°) 92.296 (4)
V (Å3)2950.3 (3)
Z8
Radiation typeMo Kα
µ (mm−1)0.45
Crystal size (mm)0.24 × 0.20 × 0.17
Data collection
DiffractometerOxford Diffraction Xcalibur Eos Gemini
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2010)
Tmin, Tmax0.900, 0.927
No. of measured, independent and
observed [I > 2σ(I)] reflections		15257, 7015, 5165
Rint0.023
(sin θ/λ)max (Å−1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.145, 1.06
No. of reflections7015
No. of parameters401
No. of restraints4
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.67, −0.57

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···F1Ai0.952.793.657 (7)152.5
C4—H4A···F1ii0.952.753.410 (5)127.0
C11—H11A···O3ii0.952.563.451 (3)155.7
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2.
Selected geometric parmeters (Å): Cg···Cg π stacking interactions, Cg1, Cg3 are the centroids of rings C1—C6 and C17—C22 [Symmetry codes: (i) x, y, z] top
CgI···CgJCg···Cg (Å)CgI Perp (Å)Cgj Perp (Å)
Cg1···Cg3i3.650 (2)3.6203.604
 

Acknowledgements

ASP thanks the University of Mysore for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

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.  CSD CrossRef Web of Science Google Scholar
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 First citationDominguez, J. N., Charris, J. E., Lobo, G., de Dominguez, N. G., Moreno, M. M., Riggione, F., Sanchez, E., Olson, J. & Rosenthal, P. J. (2001). Eur. J. Med. Chem. 36, 555–560.  Web of Science PubMed CAS Google Scholar
 First citationLi, R., Chen, X., Gong, B., Dominguez, J. N., Davidson, E., Kurzban, G., Miller, R. E., Nuzum, E. O. & Rosenthal, P. J. (1995). J. Med. Chem. 38, 5031–5037.  CrossRef CAS PubMed Web of Science Google Scholar
 First citationMei, L., Prapon, W. & Mei, L. G. (2001). J. Med. Chem. 44, 4443–4452.  Web of Science PubMed Google Scholar
 First citationOxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
 First citationSarojini, B. K., Narayana, B., Ashalatha, B. V., Indira, J. & Lobo, K. G. (2006). J. Cryst. Growth, 295, 54–59.  Web of Science CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationYathirajan, H. S., Mayekar, A. N., Narayana, B., Sarojini & Bolte, M. (2007). Acta Cryst. E63, o428–o429.  CrossRef IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 68| Part 4| April 2012| Page o1163
doi:10.1107/S1600536812011841
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