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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o739.
Published online 2009 March 11. doi:  10.1107/S1600536809007430
PMCID: PMC2968919

(E)-1-(4-Chloro­phen­yl)-3-[4-(dimethyl­amino)phen­yl]prop-2-en-1-one

Abstract

The title compound, C17H16ClNO, was synthesized using a solvent-free method by reaction of 4-(dimethyl­amino)benzaldehyde with 4-chloro­acetophenone and NaOH. The chloro­phenyl ring makes a dihedral angle of 18.1 (3)° with the central propenone unit, while the (dimethyl­amino)phenyl group is disordered over two orientations of equal occupancies, which make dihedral angles with the central propenone unit of 32.9 (3) and 57.4 (3)°, respectively.

Related literature

For a related structure, see: Li et al. (1992 [triangle]).

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Object name is e-65-0o739-scheme1.jpg

Experimental

Crystal data

  • C17H16ClNO
  • M r = 285.76
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o739-efi1.jpg
  • a = 16.792 (2) Å
  • b = 14.5602 (16) Å
  • c = 6.1160 (8) Å
  • β = 98.333 (2)°
  • V = 1479.5 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.25 mm−1
  • T = 298 K
  • 0.42 × 0.20 × 0.13 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003 [triangle]) T min = 0.901, T max = 0.968
  • 7357 measured reflections
  • 2605 independent reflections
  • 1066 reflections with I > 2˘I)
  • R int = 0.068

Refinement

  • R[F 2 > 2σ(F 2)] = 0.059
  • wR(F 2) = 0.170
  • S = 0.90
  • 2605 reflections
  • 237 parameters
  • 4 restraints
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.12 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 I, global. DOI: 10.1107/S1600536809007430/bi2339sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007430/bi2339Isup2.hkl

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

Acknowledgments

This project was supported by the Foundation of Tianshui Normal University.

supplementary crystallographic information

Comment

This paper discloses a user-friendly, solvent-free protocol for the synthesis of chalcones, starting from the fragrant aldehydes and fragrant ketones in the presence of NaOH. The method can be considered to be a general route for chalcone synthesis, and the title compound was prepared in this way.

The bond lengths and angles of the molecule (Fig. 1) are normal and comparable to those observed in the related compound (Li et al., 1992). The (dimethylamino)phenyl group exhibits rotational disorder, with one orientation including atoms C10, C11, C12, C13, C14 and C15, and another orientation including C10, C11', C12', C13, C14' and C15'. The refined site occupancy factors for the two orientations is 0.500 (5).

Experimental

4-(Dimethylamino)benzaldehyde (0.5 mmol) and 4-chloroacetophenone (0.5 mmol), NaOH (0.5 mmol) were mixed in 50 ml flask under solvent-free conditions After stirring for 6 min at 373 K, the mixture was slowly solidified to give the title compound. Recrystallization from ethanol gave a yellow crystalline solid. Elemental analysis calculated: C 71.45, H 5.64, N 4.90%; found: C 71.53, H 5.56, N 4.95%.

Refinement

All H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.96 Å and Uiso(H) = 1.2 or 1.5Ueq(C). The five-membered ring was treated as disordered between two orientations with site occupancy factors refined to 0.500 (5). The bonds N1—C16, N1—C16', N1—C17 and N1—C17' were restrained to be 1.47 (1)Å.

Figures

Fig. 1.
The molecular structure showing 30% probability displacement ellipsoids for non-H atoms.

Crystal data

C17H16ClNOF(000) = 600
Mr = 285.76Dx = 1.283 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 987 reflections
a = 16.792 (2) Åθ = 2.5–19.9°
b = 14.5602 (16) ŵ = 0.25 mm1
c = 6.1160 (8) ÅT = 298 K
β = 98.333 (2)°Needle, yellow
V = 1479.5 (3) Å30.42 × 0.20 × 0.13 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer2605 independent reflections
Radiation source: fine-focus sealed tube1066 reflections with I > 2˘I)
graphiteRint = 0.068
[var phi] and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)h = −19→19
Tmin = 0.901, Tmax = 0.968k = −17→12
7357 measured reflectionsl = −7→7

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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H-atom parameters constrained
S = 0.90w = 1/[σ2(Fo2) + (0.0749P)2] where P = (Fo2 + 2Fc2)/3
2605 reflections(Δ/σ)max < 0.001
237 parametersΔρmax = 0.16 e Å3
4 restraintsΔρmin = −0.12 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*/UeqOcc. (<1)
Cl11.12683 (6)0.14642 (9)1.2060 (3)0.1285 (7)
N10.34724 (18)0.1225 (2)0.8419 (7)0.0891 (11)
O10.80650 (17)0.1009 (2)0.4377 (6)0.1225 (12)
C10.8071 (2)0.1135 (2)0.6344 (8)0.0739 (11)
C20.8853 (2)0.1192 (2)0.7831 (7)0.0683 (10)
C30.8921 (2)0.1538 (2)0.9959 (7)0.0742 (11)
H30.84600.17121.05300.089*
C40.9663 (2)0.1627 (2)1.1247 (7)0.0801 (11)
H40.97010.18681.26660.096*
C51.0345 (2)0.1356 (3)1.0416 (9)0.0831 (12)
C61.0292 (3)0.0990 (3)0.8348 (9)0.0889 (13)
H61.07550.07920.78160.107*
C70.9552 (2)0.0914 (2)0.7048 (7)0.0792 (11)
H70.95200.06730.56290.095*
C80.7314 (2)0.1221 (2)0.7236 (7)0.0754 (11)
H80.73430.12720.87620.090*
C90.6615 (2)0.1233 (3)0.6088 (7)0.0872 (12)
H90.66170.12250.45680.105*
C100.5811 (2)0.1255 (3)0.6741 (6)0.0639 (9)
C110.5655 (5)0.0979 (6)0.8724 (14)0.055 (2)0.500 (5)
H110.60760.08210.98210.065*0.500 (5)
C120.4860 (5)0.0928 (6)0.9147 (13)0.059 (2)0.500 (5)
H120.47730.06511.04630.070*0.500 (5)
C130.4234 (2)0.1232 (2)0.7863 (7)0.0639 (10)
C140.4419 (4)0.1658 (5)0.5679 (11)0.057 (2)0.500 (5)
H140.40070.18850.46410.068*0.500 (5)
C150.5208 (4)0.1695 (5)0.5295 (12)0.059 (2)0.500 (5)
H150.53390.20120.40750.070*0.500 (5)
C160.2783 (5)0.0794 (8)0.7432 (18)0.103 (4)0.500 (5)
H16A0.25830.11020.60740.154*0.510 (7)
H16B0.23830.08150.84040.154*0.510 (7)
H16C0.29020.01660.71280.154*0.510 (7)
C170.3364 (5)0.1683 (7)1.0661 (13)0.106 (4)0.500 (5)
H17A0.38110.15261.17580.158*0.510 (7)
H17B0.28740.14661.11230.158*0.510 (7)
H17C0.33380.23371.04830.158*0.510 (7)
C11'0.5658 (5)0.1596 (6)0.8637 (16)0.060 (2)0.500 (5)
H11'0.60890.18420.95810.073*0.500 (5)
C12'0.4923 (4)0.1618 (6)0.9327 (12)0.060 (2)0.500 (5)
H12'0.48590.18701.06880.072*0.500 (5)
C14'0.4368 (4)0.0774 (5)0.6145 (12)0.059 (2)0.500 (5)
H14'0.39490.04450.53440.070*0.500 (5)
C15'0.5112 (4)0.0760 (5)0.5472 (12)0.064 (2)0.500 (5)
H15'0.51840.04360.42030.076*0.500 (5)
C16'0.2804 (4)0.1498 (7)0.6472 (14)0.090 (3)0.500 (5)
H16D0.29190.20950.59310.135*0.490 (7)
H16E0.22900.15090.69880.135*0.490 (7)
H16F0.27910.10560.53020.135*0.490 (7)
C17'0.3231 (5)0.0619 (6)0.9866 (13)0.079 (3)0.500 (5)
H17D0.34310.00190.95900.119*0.490 (7)
H17E0.26540.06040.96880.119*0.490 (7)
H17F0.34370.08041.13470.119*0.490 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0640 (8)0.1472 (12)0.1697 (14)−0.0010 (6)0.0012 (8)−0.0022 (9)
N10.053 (2)0.084 (2)0.132 (3)0.0039 (18)0.021 (2)−0.008 (3)
O10.085 (2)0.211 (4)0.078 (2)0.001 (2)0.0324 (18)0.006 (2)
C10.069 (3)0.072 (3)0.087 (3)−0.0025 (19)0.033 (2)0.000 (2)
C20.061 (2)0.061 (2)0.089 (3)−0.0045 (18)0.032 (2)0.003 (2)
C30.059 (3)0.080 (3)0.087 (3)0.0014 (18)0.024 (2)−0.003 (2)
C40.074 (3)0.075 (3)0.094 (3)−0.001 (2)0.022 (2)−0.003 (2)
C50.060 (3)0.074 (3)0.118 (4)0.003 (2)0.023 (3)0.007 (3)
C60.071 (3)0.084 (3)0.120 (4)0.003 (2)0.043 (3)−0.005 (3)
C70.074 (3)0.074 (3)0.097 (3)0.001 (2)0.037 (3)−0.007 (2)
C80.062 (2)0.090 (3)0.077 (3)−0.010 (2)0.021 (2)−0.015 (2)
C90.071 (3)0.130 (3)0.063 (3)0.021 (2)0.018 (2)0.019 (2)
C100.058 (2)0.075 (2)0.059 (3)0.007 (2)0.0076 (19)0.001 (2)
C110.050 (5)0.057 (5)0.056 (6)0.007 (4)0.003 (4)0.004 (5)
C120.069 (6)0.057 (5)0.052 (5)−0.006 (5)0.013 (4)0.000 (4)
C130.050 (2)0.054 (2)0.087 (3)0.0039 (19)0.005 (2)−0.008 (2)
C140.057 (5)0.051 (5)0.058 (5)0.002 (3)0.000 (3)0.008 (3)
C150.066 (5)0.053 (5)0.058 (5)−0.007 (4)0.012 (4)0.003 (3)
C160.076 (6)0.114 (8)0.118 (10)−0.024 (6)0.015 (6)−0.030 (7)
C170.071 (6)0.151 (9)0.098 (8)−0.002 (5)0.025 (5)−0.002 (6)
C11'0.053 (5)0.058 (6)0.067 (6)−0.005 (5)−0.001 (4)−0.012 (5)
C12'0.058 (5)0.072 (6)0.051 (5)−0.008 (5)0.011 (4)−0.008 (4)
C14'0.047 (4)0.060 (6)0.067 (5)−0.005 (3)0.000 (4)−0.011 (4)
C15'0.067 (5)0.064 (6)0.060 (5)0.005 (4)0.008 (4)−0.006 (4)
C16'0.049 (5)0.111 (8)0.105 (8)−0.001 (5)−0.001 (5)0.014 (6)
C17'0.076 (5)0.094 (7)0.071 (7)0.011 (5)0.023 (5)0.011 (5)

Geometric parameters (Å, °)

Cl1—C51.729 (4)C11—H110.930
N1—C17'1.353 (7)C12—C131.296 (8)
N1—C131.370 (4)C12—H120.930
N1—C161.377 (7)C13—C14'1.292 (7)
N1—C171.559 (7)C13—C12'1.468 (8)
N1—C16'1.565 (7)C13—C141.545 (8)
O1—C11.215 (4)C14—C151.379 (8)
C1—C81.460 (5)C14—H140.930
C1—C21.486 (5)C15—H150.930
C2—C31.385 (5)C16—H16A0.960
C2—C71.391 (4)C16—H16B0.960
C3—C41.379 (5)C16—H16C0.960
C3—H30.930C17—H17A0.960
C4—C51.376 (5)C17—H17B0.960
C4—H40.930C17—H17C0.960
C5—C61.364 (5)C11'—C12'1.362 (10)
C6—C71.380 (5)C11'—H11'0.930
C6—H60.930C12'—H12'0.930
C7—H70.930C14'—C15'1.372 (9)
C8—C91.278 (5)C14'—H14'0.930
C8—H80.930C15'—H15'0.930
C9—C101.463 (5)C16'—H16D0.960
C9—H90.930C16'—H16E0.960
C10—C11'1.320 (9)C16'—H16F0.960
C10—C111.339 (9)C17'—H17D0.960
C10—C151.399 (8)C17'—H17E0.960
C10—C15'1.495 (8)C17'—H17F0.960
C11—C121.398 (10)
C17'—N1—C13123.1 (5)N1—C13—C12'122.2 (5)
C13—N1—C16130.6 (5)C12—C13—C14114.4 (5)
C13—N1—C17116.6 (4)N1—C13—C14122.0 (4)
C16—N1—C17112.5 (5)C15—C14—C13118.8 (6)
C17'—N1—C16'114.4 (6)C15—C14—H14120.6
C13—N1—C16'113.7 (5)C13—C14—H14120.6
O1—C1—C8120.0 (4)C14—C15—C10119.9 (6)
O1—C1—C2119.6 (3)C14—C15—H15120.0
C8—C1—C2120.4 (4)C10—C15—H15120.0
C3—C2—C7118.0 (4)N1—C16—H16A109.5
C3—C2—C1122.8 (3)N1—C16—H16B109.5
C7—C2—C1119.2 (4)H16A—C16—H16B109.5
C4—C3—C2121.1 (4)N1—C16—H16C109.5
C4—C3—H3119.5H16A—C16—H16C109.5
C2—C3—H3119.5H16B—C16—H16C109.5
C5—C4—C3119.5 (4)N1—C17—H17A109.5
C5—C4—H4120.2N1—C17—H17B109.5
C3—C4—H4120.2H17A—C17—H17B109.5
C6—C5—C4120.6 (4)N1—C17—H17C109.5
C6—C5—Cl1120.5 (3)H17A—C17—H17C109.5
C4—C5—Cl1118.9 (4)H17B—C17—H17C109.5
C5—C6—C7119.8 (4)C10—C11'—C12'125.5 (7)
C5—C6—H6120.1C10—C11'—H11'117.2
C7—C6—H6120.1C12'—C11'—H11'117.2
C6—C7—C2120.9 (4)C11'—C12'—C13118.2 (7)
C6—C7—H7119.6C11'—C12'—H12'120.9
C2—C7—H7119.6C13—C12'—H12'120.9
C9—C8—C1125.2 (4)C13—C14'—C15'121.8 (6)
C9—C8—H8117.4C13—C14'—H14'119.1
C1—C8—H8117.4C15'—C14'—H14'119.1
C8—C9—C10131.4 (4)C14'—C15'—C10121.1 (6)
C8—C9—H9114.3C14'—C15'—H15'119.4
C10—C9—H9114.3C10—C15'—H15'119.4
C11—C10—C15119.4 (5)N1—C16'—H16D109.5
C11—C10—C9123.4 (4)N1—C16'—H16E109.5
C15—C10—C9116.7 (4)H16D—C16'—H16E109.5
C9—C10—C15'122.2 (4)N1—C16'—H16F109.5
C10—C11—C12120.1 (6)H16D—C16'—H16F109.5
C10—C11—H11120.0H16E—C16'—H16F109.5
C12—C11—H11120.0N1—C17'—H17D109.5
C13—C12—C11125.6 (7)N1—C17'—H17E109.5
C13—C12—H12117.2H17D—C17'—H17E109.5
C11—C12—H12117.2N1—C17'—H17F109.5
C14'—C13—N1118.5 (4)H17D—C17'—H17F109.5
C12—C13—N1123.5 (5)H17E—C17'—H17F109.5
C14'—C13—C12'118.6 (5)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2339).

References

  • Bruker (1997). SMART and SAINT Bruker AXS, Inc., Madison, Wisconsin, USA.
  • Li, Z.-D., Huang, L.-Z., Su, G.-B. & Wang, H.-Y. (1992). Chin. J. Struct. Chem.11, 1–4.
  • Sheldrick, G. M. (2003). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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