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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2302.
Published online 2010 August 18. doi:  10.1107/S1600536810031880
PMCID: PMC3008096

1-(4-Chloro­phen­yl)-3-(3,4-dimethyl­phen­yl)prop-2-en-1-one

Abstract

The title compound, C17H15ClO, was prepared from 3,4-dimethyl­benzaldehyde and 4-chloro­hypnone by Aldol condensation. The dihedral angle formed by the two benzene rings is 48.91 (8)°. Only van der Waals forces affect the packing.

Related literature

For background to the aplications of chalcones, see: Anto et al. (1994 [triangle]); Hsieh et al. (1998 [triangle]). For a related structure, see: Zhou (2010 [triangle]).

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Object name is e-66-o2302-scheme1.jpg

Experimental

Crystal data

  • C17H15ClO
  • M r = 270.74
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2302-efi1.jpg
  • a = 5.9621 (12) Å
  • b = 7.7369 (15) Å
  • c = 15.513 (3) Å
  • α = 98.30 (3)°
  • β = 99.96 (3)°
  • γ = 95.23 (3)°
  • V = 692.5 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.26 mm−1
  • T = 293 K
  • 0.25 × 0.20 × 0.18 mm

Data collection

  • Bruker SMART CCD diffractometer
  • 6689 measured reflections
  • 3141 independent reflections
  • 2643 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.061
  • wR(F 2) = 0.188
  • S = 1.08
  • 3141 reflections
  • 172 parameters
  • H-atom parameters constrained
  • Δρmax = 0.54 e Å−3
  • Δρmin = −0.52 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810031880/hb5576sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031880/hb5576Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The author thanks the National Natural Science Foundation of Shandong (Y2008B29) and Weifang University for research grants.

supplementary crystallographic information

Comment

Among flavonoids, chalcones have been identified as interesting compounds having multiple biological actions which include antiinflammatory (Hsieh et al.,1998) and antioxidant (Anto et al.,1994). As part of our search for new biologically active compounds we synthesized the title compound (I) and report its crystal structure herein.

In the crystal structure of compound(I)(Fig.1),the dihedral angle between the two benzene rings(C1—C6) and (C10—C15) is 48.91 (8)°. All of the bond lengths and bond angles are in normal ranges and comparable to those in a related structure (Zhou,2010).

Experimental

A mixture of the 4-chlorohypnone (0.01 mol) and 3,4-dimethylbenzaldehyde(0.01 mol) and 10% NaOH (10 ml) was stirred in ethanol (30 ml) for 3 h to afford the title compound (yield 65%). Yellow bars of (I) were obtailed by recrystallization from ethyl acetate at room temperature.

Refinement

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H distances of 0.93–0.96 Å, and with Uiso(H) = 1.2-1.5Ueq of the parent atoms.

Figures

Fig. 1.
The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level.

Crystal data

C17H15ClOZ = 2
Mr = 270.74F(000) = 284
Triclinic, P1Dx = 1.299 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.9621 (12) ÅCell parameters from 2643 reflections
b = 7.7369 (15) Åθ = 3.2–27.5°
c = 15.513 (3) ŵ = 0.26 mm1
α = 98.30 (3)°T = 293 K
β = 99.96 (3)°Bar, yellow
γ = 95.23 (3)°0.25 × 0.20 × 0.18 mm
V = 692.5 (2) Å3

Data collection

Bruker SMART CCD diffractometer2643 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
graphiteθmax = 27.5°, θmin = 3.2°
phi and ω scansh = −7→7
6689 measured reflectionsk = −10→10
3141 independent reflectionsl = −20→18

Refinement

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) = 0.188H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.1287P)2 + 0.0873P] where P = (Fo2 + 2Fc2)/3
3141 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.54 e Å3
0 restraintsΔρmin = −0.52 e Å3

Special details

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)

xyzUiso*/Ueq
Cl10.06653 (10)0.43200 (7)−0.40023 (3)0.0645 (2)
C20.2286 (3)0.4248 (2)−0.22733 (12)0.0442 (4)
H2A0.36750.4759−0.23700.053*
C150.3097 (3)0.2253 (2)0.26373 (11)0.0398 (4)
H15A0.18220.27630.27740.048*
C100.3326 (3)0.1916 (2)0.17512 (11)0.0372 (4)
C10.0394 (3)0.3865 (2)−0.29529 (11)0.0419 (4)
C90.1543 (3)0.2354 (2)0.10668 (11)0.0405 (4)
H9A0.01940.26440.12450.049*
C7−0.0361 (3)0.2764 (2)−0.04009 (11)0.0417 (4)
C6−0.1707 (3)0.3131 (2)−0.28266 (12)0.0476 (4)
H6A−0.29590.2877−0.32930.057*
O1−0.2265 (2)0.2775 (2)−0.02091 (9)0.0582 (4)
C110.5261 (3)0.1151 (2)0.15544 (12)0.0425 (4)
H11A0.54900.09420.09720.051*
C80.1647 (3)0.2382 (2)0.02181 (12)0.0449 (4)
H8A0.29870.21610.00130.054*
C4−0.0022 (3)0.3133 (2)−0.12946 (10)0.0369 (4)
C30.2072 (3)0.3857 (2)−0.14451 (11)0.0425 (4)
H3A0.33400.4081−0.09850.051*
C120.6825 (3)0.0710 (2)0.22314 (12)0.0445 (4)
H12A0.80840.01810.20920.053*
C140.4693 (3)0.1859 (2)0.33241 (11)0.0412 (4)
C130.6579 (3)0.1031 (2)0.31155 (12)0.0417 (4)
C5−0.1902 (3)0.2784 (2)−0.19930 (12)0.0441 (4)
H5A−0.33090.2311−0.18950.053*
C170.4398 (4)0.2300 (4)0.42722 (13)0.0626 (6)
H17A0.56470.19380.46570.094*
H17B0.29770.16970.43430.094*
H17C0.43810.35460.44220.094*
C160.8291 (4)0.0483 (3)0.38260 (15)0.0594 (5)
H16A0.9448−0.00630.35620.089*
H16B0.7525−0.03380.41190.089*
H16C0.89940.14990.42500.089*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0855 (4)0.0709 (4)0.0412 (3)0.0036 (3)0.0171 (2)0.0203 (2)
C20.0418 (8)0.0477 (9)0.0442 (9)−0.0002 (7)0.0126 (7)0.0093 (7)
C150.0371 (7)0.0445 (8)0.0399 (8)0.0054 (6)0.0118 (6)0.0086 (7)
C100.0372 (7)0.0368 (7)0.0384 (8)0.0012 (6)0.0094 (6)0.0085 (6)
C10.0527 (9)0.0393 (8)0.0353 (8)0.0056 (7)0.0108 (7)0.0087 (6)
C90.0418 (8)0.0423 (8)0.0391 (8)0.0037 (6)0.0106 (6)0.0094 (6)
C70.0433 (8)0.0462 (8)0.0369 (8)0.0062 (6)0.0105 (6)0.0067 (7)
C60.0450 (8)0.0537 (10)0.0407 (9)0.0009 (7)−0.0002 (7)0.0092 (7)
O10.0451 (7)0.0882 (10)0.0464 (7)0.0088 (6)0.0163 (5)0.0177 (7)
C110.0449 (8)0.0433 (8)0.0411 (9)0.0041 (7)0.0150 (7)0.0052 (7)
C80.0457 (8)0.0541 (10)0.0383 (8)0.0103 (7)0.0119 (7)0.0116 (7)
C40.0385 (7)0.0377 (7)0.0353 (8)0.0056 (6)0.0084 (6)0.0058 (6)
C30.0371 (7)0.0493 (9)0.0390 (8)0.0010 (6)0.0049 (6)0.0053 (7)
C120.0410 (8)0.0414 (8)0.0527 (10)0.0064 (6)0.0139 (7)0.0056 (7)
C140.0397 (8)0.0463 (8)0.0387 (8)0.0012 (6)0.0108 (6)0.0090 (7)
C130.0384 (8)0.0386 (8)0.0475 (9)0.0010 (6)0.0058 (7)0.0102 (7)
C50.0374 (8)0.0494 (9)0.0443 (9)−0.0002 (7)0.0058 (7)0.0093 (7)
C170.0549 (10)0.0958 (16)0.0399 (9)0.0154 (10)0.0116 (8)0.0130 (10)
C160.0561 (10)0.0655 (12)0.0585 (12)0.0147 (9)0.0040 (9)0.0194 (10)

Geometric parameters (Å, °)

Cl1—C11.7455 (17)C11—H11A0.9300
C2—C11.382 (3)C8—H8A0.9300
C2—C31.386 (3)C4—C31.392 (2)
C2—H2A0.9300C4—C51.394 (2)
C15—C141.389 (2)C3—H3A0.9300
C15—C101.394 (2)C12—C131.394 (2)
C15—H15A0.9300C12—H12A0.9300
C10—C111.403 (2)C14—C131.406 (2)
C10—C91.467 (2)C14—C171.505 (3)
C1—C61.385 (3)C13—C161.504 (2)
C9—C81.332 (2)C5—H5A0.9300
C9—H9A0.9300C17—H17A0.9600
C7—O11.222 (2)C17—H17B0.9600
C7—C81.481 (2)C17—H17C0.9600
C7—C41.499 (2)C16—H16A0.9600
C6—C51.380 (3)C16—H16B0.9600
C6—H6A0.9300C16—H16C0.9600
C11—C121.383 (3)
C1—C2—C3118.67 (15)C5—C4—C7118.34 (15)
C1—C2—H2A120.7C2—C3—C4120.69 (15)
C3—C2—H2A120.7C2—C3—H3A119.7
C14—C15—C10122.73 (15)C4—C3—H3A119.7
C14—C15—H15A118.6C11—C12—C13122.25 (15)
C10—C15—H15A118.6C11—C12—H12A118.9
C15—C10—C11118.03 (15)C13—C12—H12A118.9
C15—C10—C9119.14 (14)C15—C14—C13118.70 (15)
C11—C10—C9122.83 (15)C15—C14—C17120.56 (15)
C2—C1—C6122.03 (16)C13—C14—C17120.74 (16)
C2—C1—Cl1118.89 (13)C12—C13—C14118.63 (15)
C6—C1—Cl1119.08 (13)C12—C13—C16120.30 (16)
C8—C9—C10127.04 (15)C14—C13—C16121.07 (16)
C8—C9—H9A116.5C6—C5—C4121.01 (16)
C10—C9—H9A116.5C6—C5—H5A119.5
O1—C7—C8122.36 (16)C4—C5—H5A119.5
O1—C7—C4119.56 (16)C14—C17—H17A109.5
C8—C7—C4118.08 (14)C14—C17—H17B109.5
C5—C6—C1118.51 (15)H17A—C17—H17B109.5
C5—C6—H6A120.7C14—C17—H17C109.5
C1—C6—H6A120.7H17A—C17—H17C109.5
C12—C11—C10119.58 (15)H17B—C17—H17C109.5
C12—C11—H11A120.2C13—C16—H16A109.5
C10—C11—H11A120.2C13—C16—H16B109.5
C9—C8—C7120.28 (16)H16A—C16—H16B109.5
C9—C8—H8A119.9C13—C16—H16C109.5
C7—C8—H8A119.9H16A—C16—H16C109.5
C3—C4—C5119.06 (15)H16B—C16—H16C109.5
C3—C4—C7122.57 (14)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5576).

References

  • Anto, R. J., Kuttan, G., Kuttan, R., Sathyanarayana, K. & Rao, M. N. A. (1994). J. Clin. Biochem. Nutr.17, 73–80.
  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Hsieh, H. K., Lee, T. H., Wang, J. P., Wang, J. J. & Lin, C. N. (1998). Pharm. Res.15, 39–46. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhou, Y. (2010). Acta Cryst. E66, o1412. [PMC free article] [PubMed]

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