organic compounds
1-(2,4-Dichlorophenyl)-3-(4-methylphenyl)prop-2-en-1-one
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India
*Correspondence e-mail: hkfun@usm.my
The molecule of the title compound, C16H12Cl2O, adopts an E configuration. The dihedral angle between the two benzene rings is 42.09 (5)°. In the molecules are linked into a three-dimensional framework by weak C—H⋯O interactions and by C—H⋯π interactions involving the methylphenyl ring.
Related literature
For related literature, see: Agrinskaya et al. (1999); Gu et al. (2008); Patil et al. (2006); Patil, Dharmaprakash et al. (2007); Patil, Teh et al. (2007).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
Supporting information
10.1107/S1600536808011008/ci2584sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808011008/ci2584Isup2.hkl
The title compound was synthesized by the condensation of p-tolualdehyde (0.01 mol) with 2,4-dichloroacetophenone (0.01 mol) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (5 ml, 30%). After stirring for 2 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 collected by filtration and dried. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of an acetone solution at room temperature.
H atoms were positioned geometrically [C-H = 0.93 (aromatic) or 0.96 Å (methyl)] and refined using a riding model, with Uiso(H) = 1.5Ueq(methyl C) or 1.2Ueq(C).
Data collection: APEX2 (Bruker, 2005); cell
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).C16H12Cl2O | F(000) = 1200 |
Mr = 291.16 | Dx = 1.432 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 9639 reflections |
a = 12.54850 (1) Å | θ = 2.8–34.6° |
b = 7.47750 (1) Å | µ = 0.47 mm−1 |
c = 28.7764 (3) Å | T = 100 K |
V = 2700.13 (3) Å3 | Block, colourless |
Z = 8 | 0.47 × 0.39 × 0.20 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 7296 independent reflections |
Radiation source: fine-focus sealed tube | 4995 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
ϕ and ω scans | θmax = 37.9°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −21→21 |
Tmin = 0.811, Tmax = 0.914 | k = −12→12 |
50054 measured reflections | l = −48→49 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.078P)2 + 0.0443P] where P = (Fo2 + 2Fc2)/3 |
7296 reflections | (Δ/σ)max = 0.001 |
173 parameters | Δρmax = 0.64 e Å−3 |
0 restraints | Δρmin = −0.53 e Å−3 |
C16H12Cl2O | V = 2700.13 (3) Å3 |
Mr = 291.16 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 12.54850 (1) Å | µ = 0.47 mm−1 |
b = 7.47750 (1) Å | T = 100 K |
c = 28.7764 (3) Å | 0.47 × 0.39 × 0.20 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 7296 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 4995 reflections with I > 2σ(I) |
Tmin = 0.811, Tmax = 0.914 | Rint = 0.052 |
50054 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.64 e Å−3 |
7296 reflections | Δρmin = −0.53 e Å−3 |
173 parameters |
Experimental. The 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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.46470 (2) | 0.76088 (4) | 0.057148 (10) | 0.02125 (8) | |
Cl2 | 0.36980 (3) | 0.56187 (5) | −0.116828 (9) | 0.02538 (9) | |
O1 | 0.13288 (7) | 0.72551 (12) | 0.08499 (3) | 0.02032 (17) | |
C1 | 0.37202 (9) | 0.67308 (15) | 0.01850 (4) | 0.0158 (2) | |
C2 | 0.40554 (10) | 0.64861 (15) | −0.02709 (4) | 0.0177 (2) | |
H2 | 0.4759 | 0.6696 | −0.0356 | 0.021* | |
C3 | 0.33080 (10) | 0.59184 (15) | −0.05947 (4) | 0.0177 (2) | |
C4 | 0.22518 (9) | 0.56292 (16) | −0.04764 (4) | 0.0183 (2) | |
H4 | 0.1760 | 0.5265 | −0.0699 | 0.022* | |
C5 | 0.19470 (9) | 0.58948 (15) | −0.00210 (4) | 0.0173 (2) | |
H5 | 0.1238 | 0.5715 | 0.0060 | 0.021* | |
C6 | 0.26690 (9) | 0.64245 (14) | 0.03220 (3) | 0.01531 (19) | |
C7 | 0.22310 (9) | 0.66606 (15) | 0.08060 (4) | 0.0165 (2) | |
C8 | 0.28861 (9) | 0.60913 (15) | 0.12039 (4) | 0.0168 (2) | |
H8 | 0.3512 | 0.5458 | 0.1151 | 0.020* | |
C9 | 0.25956 (10) | 0.64712 (15) | 0.16419 (4) | 0.0168 (2) | |
H9 | 0.1962 | 0.7100 | 0.1680 | 0.020* | |
C10 | 0.31720 (9) | 0.59981 (15) | 0.20655 (4) | 0.01556 (19) | |
C11 | 0.27256 (10) | 0.64353 (15) | 0.24970 (4) | 0.0179 (2) | |
H11 | 0.2075 | 0.7031 | 0.2508 | 0.021* | |
C12 | 0.32405 (10) | 0.59919 (16) | 0.29076 (4) | 0.0189 (2) | |
H12 | 0.2929 | 0.6294 | 0.3190 | 0.023* | |
C13 | 0.42150 (10) | 0.51030 (16) | 0.29039 (4) | 0.0182 (2) | |
C14 | 0.46702 (9) | 0.46835 (16) | 0.24731 (4) | 0.0185 (2) | |
H14 | 0.5325 | 0.4102 | 0.2463 | 0.022* | |
C15 | 0.41598 (9) | 0.51215 (16) | 0.20617 (4) | 0.0177 (2) | |
H15 | 0.4476 | 0.4831 | 0.1779 | 0.021* | |
C16 | 0.47564 (11) | 0.45835 (18) | 0.33516 (4) | 0.0251 (3) | |
H16A | 0.4802 | 0.5608 | 0.3552 | 0.038* | |
H16B | 0.5460 | 0.4149 | 0.3286 | 0.038* | |
H16C | 0.4352 | 0.3662 | 0.3503 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.01778 (15) | 0.02973 (16) | 0.01623 (13) | −0.00376 (10) | −0.00292 (9) | −0.00163 (10) |
Cl2 | 0.02586 (17) | 0.03750 (18) | 0.01277 (12) | 0.00235 (12) | 0.00091 (10) | −0.00154 (10) |
O1 | 0.0168 (4) | 0.0256 (4) | 0.0185 (4) | 0.0022 (3) | −0.0001 (3) | −0.0017 (3) |
C1 | 0.0158 (5) | 0.0171 (5) | 0.0145 (4) | 0.0009 (4) | −0.0025 (4) | −0.0003 (3) |
C2 | 0.0158 (5) | 0.0216 (5) | 0.0157 (4) | 0.0016 (4) | 0.0004 (4) | 0.0001 (4) |
C3 | 0.0213 (6) | 0.0200 (5) | 0.0117 (4) | 0.0020 (4) | −0.0010 (4) | 0.0007 (3) |
C4 | 0.0183 (5) | 0.0210 (5) | 0.0156 (4) | −0.0001 (4) | −0.0043 (4) | −0.0007 (4) |
C5 | 0.0166 (5) | 0.0198 (5) | 0.0154 (4) | −0.0007 (4) | −0.0014 (4) | 0.0005 (4) |
C6 | 0.0177 (5) | 0.0155 (4) | 0.0127 (4) | 0.0013 (4) | −0.0010 (4) | 0.0012 (3) |
C7 | 0.0191 (5) | 0.0152 (4) | 0.0153 (4) | −0.0006 (4) | 0.0005 (4) | −0.0008 (3) |
C8 | 0.0188 (5) | 0.0172 (5) | 0.0144 (4) | 0.0018 (4) | 0.0001 (4) | 0.0001 (3) |
C9 | 0.0170 (5) | 0.0173 (5) | 0.0159 (4) | −0.0006 (4) | 0.0003 (4) | −0.0001 (3) |
C10 | 0.0177 (5) | 0.0163 (4) | 0.0127 (4) | −0.0004 (4) | 0.0012 (4) | −0.0001 (3) |
C11 | 0.0180 (5) | 0.0200 (5) | 0.0156 (4) | 0.0021 (4) | 0.0006 (4) | −0.0008 (4) |
C12 | 0.0222 (6) | 0.0218 (5) | 0.0126 (4) | 0.0004 (4) | 0.0013 (4) | −0.0008 (4) |
C13 | 0.0204 (6) | 0.0184 (5) | 0.0158 (5) | −0.0024 (4) | −0.0019 (4) | 0.0007 (4) |
C14 | 0.0168 (5) | 0.0207 (5) | 0.0179 (5) | 0.0013 (4) | 0.0002 (4) | 0.0001 (4) |
C15 | 0.0175 (5) | 0.0209 (5) | 0.0149 (4) | 0.0013 (4) | 0.0009 (4) | −0.0002 (4) |
C16 | 0.0284 (7) | 0.0290 (6) | 0.0179 (5) | 0.0016 (5) | −0.0058 (5) | 0.0011 (4) |
Cl1—C1 | 1.7380 (11) | C9—C10 | 1.4609 (15) |
Cl2—C3 | 1.7360 (11) | C9—H9 | 0.93 |
O1—C7 | 1.2228 (14) | C10—C11 | 1.4008 (15) |
C1—C2 | 1.3895 (15) | C10—C15 | 1.4022 (17) |
C1—C6 | 1.3957 (16) | C11—C12 | 1.3871 (16) |
C2—C3 | 1.3887 (16) | C11—H11 | 0.93 |
C2—H2 | 0.93 | C12—C13 | 1.3919 (18) |
C3—C4 | 1.3854 (17) | C12—H12 | 0.93 |
C4—C5 | 1.3795 (15) | C13—C14 | 1.4006 (16) |
C4—H4 | 0.93 | C13—C16 | 1.5072 (16) |
C5—C6 | 1.3971 (15) | C14—C15 | 1.3855 (16) |
C5—H5 | 0.93 | C14—H14 | 0.93 |
C6—C7 | 1.5077 (15) | C15—H15 | 0.93 |
C7—C8 | 1.4725 (15) | C16—H16A | 0.96 |
C8—C9 | 1.3424 (14) | C16—H16B | 0.96 |
C8—H8 | 0.93 | C16—H16C | 0.96 |
C2—C1—C6 | 122.08 (10) | C10—C9—H9 | 116.6 |
C2—C1—Cl1 | 116.83 (9) | C11—C10—C15 | 118.00 (10) |
C6—C1—Cl1 | 120.90 (8) | C11—C10—C9 | 119.02 (10) |
C3—C2—C1 | 118.00 (11) | C15—C10—C9 | 122.98 (10) |
C3—C2—H2 | 121.0 | C12—C11—C10 | 120.88 (11) |
C1—C2—H2 | 121.0 | C12—C11—H11 | 119.6 |
C4—C3—C2 | 121.92 (10) | C10—C11—H11 | 119.6 |
C4—C3—Cl2 | 118.90 (9) | C11—C12—C13 | 121.12 (10) |
C2—C3—Cl2 | 119.15 (10) | C11—C12—H12 | 119.4 |
C5—C4—C3 | 118.45 (10) | C13—C12—H12 | 119.4 |
C5—C4—H4 | 120.8 | C12—C13—C14 | 118.17 (10) |
C3—C4—H4 | 120.8 | C12—C13—C16 | 120.83 (10) |
C4—C5—C6 | 122.15 (11) | C14—C13—C16 | 120.99 (11) |
C4—C5—H5 | 118.9 | C15—C14—C13 | 121.00 (11) |
C6—C5—H5 | 118.9 | C15—C14—H14 | 119.5 |
C1—C6—C5 | 117.38 (10) | C13—C14—H14 | 119.5 |
C1—C6—C7 | 125.90 (10) | C14—C15—C10 | 120.83 (10) |
C5—C6—C7 | 116.70 (10) | C14—C15—H15 | 119.6 |
O1—C7—C8 | 122.79 (10) | C10—C15—H15 | 119.6 |
O1—C7—C6 | 118.40 (10) | C13—C16—H16A | 109.5 |
C8—C7—C6 | 118.75 (10) | C13—C16—H16B | 109.5 |
C9—C8—C7 | 121.15 (11) | H16A—C16—H16B | 109.5 |
C9—C8—H8 | 119.4 | C13—C16—H16C | 109.5 |
C7—C8—H8 | 119.4 | H16A—C16—H16C | 109.5 |
C8—C9—C10 | 126.71 (11) | H16B—C16—H16C | 109.5 |
C8—C9—H9 | 116.6 | ||
C6—C1—C2—C3 | 0.00 (17) | C5—C6—C7—C8 | 141.55 (11) |
Cl1—C1—C2—C3 | −175.09 (9) | O1—C7—C8—C9 | −11.25 (18) |
C1—C2—C3—C4 | 1.20 (17) | C6—C7—C8—C9 | 171.61 (10) |
C1—C2—C3—Cl2 | 179.44 (9) | C7—C8—C9—C10 | −179.61 (11) |
C2—C3—C4—C5 | −0.88 (17) | C8—C9—C10—C11 | −177.16 (12) |
Cl2—C3—C4—C5 | −179.12 (9) | C8—C9—C10—C15 | 2.91 (19) |
C3—C4—C5—C6 | −0.67 (17) | C15—C10—C11—C12 | −0.83 (17) |
C2—C1—C6—C5 | −1.44 (17) | C9—C10—C11—C12 | 179.24 (11) |
Cl1—C1—C6—C5 | 173.45 (9) | C10—C11—C12—C13 | 0.09 (19) |
C2—C1—C6—C7 | −179.70 (10) | C11—C12—C13—C14 | 0.69 (18) |
Cl1—C1—C6—C7 | −4.80 (16) | C11—C12—C13—C16 | −178.42 (11) |
C4—C5—C6—C1 | 1.79 (17) | C12—C13—C14—C15 | −0.73 (18) |
C4—C5—C6—C7 | −179.80 (10) | C16—C13—C14—C15 | 178.38 (11) |
C1—C6—C7—O1 | 142.55 (12) | C13—C14—C15—C10 | −0.01 (18) |
C5—C6—C7—O1 | −35.72 (15) | C11—C10—C15—C14 | 0.79 (17) |
C1—C6—C7—C8 | −40.19 (15) | C9—C10—C15—C14 | −179.29 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1i | 0.93 | 2.55 | 3.4352 (15) | 159 |
C8—H8···O1ii | 0.93 | 2.55 | 3.1995 (14) | 127 |
C11—H11···Cg1iii | 0.93 | 2.81 | 3.5611 (13) | 139 |
C14—H14···Cg1iv | 0.93 | 2.93 | 3.7066 (13) | 142 |
Symmetry codes: (i) x+1/2, −y+3/2, −z; (ii) −x+1/2, y−1/2, z; (iii) −x+1/2, y+1/2, z; (iv) −x+1, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C16H12Cl2O |
Mr | 291.16 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 100 |
a, b, c (Å) | 12.54850 (1), 7.47750 (1), 28.7764 (3) |
V (Å3) | 2700.13 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.47 |
Crystal size (mm) | 0.47 × 0.39 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.811, 0.914 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 50054, 7296, 4995 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.864 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.148, 1.07 |
No. of reflections | 7296 |
No. of parameters | 173 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.64, −0.53 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1i | 0.93 | 2.55 | 3.4352 (15) | 159 |
C8—H8···O1ii | 0.93 | 2.55 | 3.1995 (14) | 127 |
C11—H11···Cg1iii | 0.93 | 2.81 | 3.5611 (13) | 139 |
C14—H14···Cg1iv | 0.93 | 2.93 | 3.7066 (13) | 142 |
Symmetry codes: (i) x+1/2, −y+3/2, −z; (ii) −x+1/2, y−1/2, z; (iii) −x+1/2, y+1/2, z; (iv) −x+1, y−1/2, −z+1/2. |
Footnotes
‡Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.
Acknowledgements
FHK and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks the Universiti Sains Malaysia for the award of a post-doctoral research fellowship. PSP thanks the DRDO, Government of India, for a Senior Research Fellowship (SRF). This work is also supported by the Department of Science and Technology (DST), Government of India, under grant No. SR/S2/LOP-17/2006.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Chalcone derivatives have been studied extensively owing to their fascinating, technologically relevant nonlinear optical properties (Gu et al., 2008; Agrinskaya et al., 1999; Patil et al., 2006; Patil, Dharmaprakash et al., 2007; Patil, Teh et al., 2007).
The title molecule exhibits an E configuration with respect to the C8═C9 double bond [1.3424 (14) Å]; the C7—C8—-C9—-C10 torsion angle is 179.61 (11)°. The dihedral angle between the two benzene rings is 42.09 (5)°. The bond lengths and angles in the title molecule have normal values.
The crystal structure is stabilized by weak C—H···O intermolecular hydrogen bonding interactions (Table 1), which link the molecules into a three-dimensional framework (Fig. 2). In addition weak C—H..π interactions involving the C10—C15 benzene ring (centroid Cg1) is observed.