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Acta Cryst. (2009). E65, o1266    [ doi:10.1107/S1600536809015177 ]

1-(2,4-Dichlorophenyl)-3-[4-(dimethylamino)phenyl]prop-2-enone

N. N. Bappalige, Brinda, Y. Narayana and V. Upadyaya

Abstract top

In the title compound, C17H15Cl2NO, the dimethylaminophenyl group is close to coplanar with the central propenone group [dihedral angle = 13.1 (1)° between the mean planes], while the dichlorophenyl group is twisted from the plane [dihedral angle = 64.0 (1)°]. In the crystal, C-H...O and weak C-H...[pi] interactions are formed between molecules.

Related literature top

For related structures, see: Murafuji et al. (1999); Liu et al. (2002); Patil et al. (2007a,b); Rosli et al. (2007). Cg1 is the centroid of the C10–C15 ring.

Experimental top

A solution of potassium hydroxide (6.25 g, 0.11 mol) in ethanol (25 ml) was added slowly to a mixture of dichloroacetophenone (18.8 g, 0.01 mol) and N-dimethyl benzaldehyde (14.9 g, 0.01 mol) in a conical flask. After stirring for two hours, the precipitate was filtered and recrystallized from ethanol to give pale orange crystals.

Refinement top

H atoms were positioned geometrically with C—H bond lengths of 0.93–0.96 Å and refined using a riding model with Uiso(H) = 1.2 or 1.5Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure with displacement ellipsoids drawn at the 50% probability level for non-H atoms. H atoms are shown as small spheres of arbitrary radius.
[Figure 2] Fig. 2. Packing diagram. The dotted lines indicate intermolecular C—H···O and C—H···π interactions.
1-(2,4-Dichlorophenyl)-3-[4-(dimethylamino)phenyl]prop-2-enone top
Crystal data top
C17H15Cl2NOF000 = 664
Mr = 320.20Dx = 1.364 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3980 reflections
a = 8.5741 (19) Åθ = 2.0–26.0º
b = 12.706 (3) ŵ = 0.41 mm−1
c = 14.671 (3) ÅT = 290 K
β = 102.645 (4)ºBlock, orange
V = 1559.5 (6) Å30.25 × 0.15 × 0.07 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		2908 independent reflections
Radiation source: fine-focus sealed tube2039 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.031
T = 290 Kθmax = 25.5º
φ and ω scansθmin = 2.1º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −10→10
Tmin = 0.923, Tmax = 0.972k = −15→15
11540 measured reflectionsl = −16→17
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.106  w = 1/[σ2(Fo2) + (0.0505P)2 + 0.1972P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2908 reflectionsΔρmax = 0.20 e Å−3
192 parametersΔρmin = −0.17 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C17H15Cl2NOV = 1559.5 (6) Å3
Mr = 320.20Z = 4
Monoclinic, P21/cMo Kα
a = 8.5741 (19) ŵ = 0.41 mm−1
b = 12.706 (3) ÅT = 290 K
c = 14.671 (3) Å0.25 × 0.15 × 0.07 mm
β = 102.645 (4)º
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		2908 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2039 reflections with I > 2σ(I)
Tmin = 0.923, Tmax = 0.972Rint = 0.031
11540 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.042192 parameters
wR(F2) = 0.106H-atom parameters constrained
S = 1.03Δρmax = 0.20 e Å−3
2908 reflectionsΔρmin = −0.17 e Å−3
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*/Ueq
Cl10.42606 (8)−0.03118 (5)0.21634 (5)0.0704 (2)
Cl20.33039 (10)0.29372 (6)0.42942 (5)0.0851 (3)
C130.2618 (2)0.71607 (15)−0.03057 (14)0.0421 (5)
C100.1972 (2)0.54646 (15)0.08139 (14)0.0414 (5)
C90.1721 (2)0.45849 (17)0.13874 (15)0.0461 (5)
H90.22440.39640.12990.055*
C150.2754 (2)0.53119 (16)0.00809 (15)0.0459 (5)
H150.30780.4636−0.00370.055*
C80.0829 (3)0.45512 (17)0.20297 (16)0.0508 (6)
H80.02470.51510.21010.061*
N10.2898 (2)0.79802 (13)−0.08543 (13)0.0518 (5)
C120.1844 (3)0.73163 (16)0.04341 (14)0.0481 (5)
H120.15480.79930.05680.058*
C60.1595 (2)0.26655 (16)0.25224 (16)0.0469 (5)
C30.3204 (3)0.08209 (17)0.23089 (17)0.0509 (6)
C140.3057 (2)0.61262 (16)−0.04685 (14)0.0456 (5)
H140.35610.599−0.09570.055*
C40.3608 (3)0.13662 (17)0.31339 (16)0.0519 (6)
H40.44250.11290.36160.062*
C110.1517 (2)0.64926 (17)0.09597 (15)0.0476 (5)
H110.09720.66220.14310.057*
C70.0693 (3)0.36611 (18)0.26236 (17)0.0547 (6)
O1−0.0115 (2)0.37083 (15)0.32101 (14)0.0849 (6)
C50.2780 (3)0.22710 (17)0.32357 (15)0.0501 (5)
C20.2015 (3)0.11710 (19)0.15886 (17)0.0576 (6)
H20.17370.0790.10360.069*
C170.2722 (3)0.90604 (18)−0.05879 (18)0.0685 (7)
H17A0.16250.9193−0.05740.103*
H17B0.3040.9521−0.10330.103*
H17C0.33830.91850.00210.103*
C160.3630 (3)0.77905 (19)−0.16414 (17)0.0665 (7)
H16A0.47250.7587−0.14170.1*
H16B0.35840.8422−0.20060.1*
H16C0.30640.7238−0.20220.1*
C10.1244 (3)0.20911 (18)0.16968 (17)0.0577 (6)
H10.0460.23390.12020.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0823 (5)0.0539 (4)0.0800 (5)0.0084 (3)0.0288 (4)0.0038 (3)
Cl20.1090 (6)0.0798 (5)0.0577 (4)0.0164 (4)−0.0008 (4)−0.0118 (3)
C130.0447 (12)0.0425 (12)0.0377 (11)−0.0018 (9)0.0062 (9)0.0013 (9)
C100.0437 (11)0.0407 (12)0.0406 (12)0.0008 (9)0.0110 (10)0.0024 (9)
C90.0442 (12)0.0439 (12)0.0499 (13)0.0026 (9)0.0098 (10)0.0023 (10)
C150.0531 (13)0.0363 (11)0.0508 (13)0.0034 (10)0.0166 (11)−0.0031 (10)
C80.0476 (12)0.0472 (13)0.0604 (15)0.0057 (10)0.0178 (11)0.0116 (11)
N10.0671 (12)0.0415 (10)0.0496 (11)−0.0017 (9)0.0187 (9)0.0063 (8)
C120.0629 (14)0.0365 (11)0.0466 (13)0.0078 (10)0.0158 (11)0.0002 (9)
C60.0451 (12)0.0426 (12)0.0546 (14)−0.0054 (10)0.0142 (11)0.0104 (10)
C30.0543 (14)0.0443 (13)0.0585 (15)−0.0036 (10)0.0219 (12)0.0083 (11)
C140.0524 (13)0.0448 (12)0.0430 (12)0.0010 (10)0.0176 (10)−0.0010 (10)
C40.0545 (13)0.0502 (13)0.0496 (14)0.0017 (11)0.0081 (11)0.0124 (11)
C110.0556 (13)0.0496 (13)0.0413 (12)0.0050 (10)0.0189 (10)0.0009 (10)
C70.0451 (12)0.0573 (14)0.0645 (15)−0.0020 (11)0.0181 (12)0.0118 (12)
O10.0906 (13)0.0778 (13)0.1068 (15)0.0194 (10)0.0665 (12)0.0326 (11)
C50.0550 (13)0.0484 (13)0.0480 (13)−0.0035 (11)0.0135 (11)0.0069 (10)
C20.0610 (15)0.0550 (15)0.0539 (14)−0.0095 (12)0.0061 (12)−0.0027 (11)
C170.0926 (19)0.0432 (14)0.0702 (17)−0.0039 (13)0.0186 (15)0.0076 (12)
C160.0852 (18)0.0624 (16)0.0571 (15)−0.0086 (13)0.0268 (14)0.0111 (12)
C10.0508 (13)0.0598 (15)0.0562 (15)−0.0032 (12)−0.0019 (11)0.0079 (12)
Geometric parameters (Å, °) top
Cl1—C31.738 (2)C6—C11.389 (3)
Cl2—C51.739 (2)C6—C71.507 (3)
C13—N11.369 (2)C3—C41.372 (3)
C13—C141.402 (3)C3—C21.372 (3)
C13—C121.405 (3)C14—H140.930
C10—C111.393 (3)C4—C51.376 (3)
C10—C151.400 (3)C4—H40.9300
C10—C91.443 (3)C11—H110.930
C9—C81.338 (3)C7—O11.218 (3)
C9—H90.930C2—C11.369 (3)
C15—C141.371 (3)C2—H20.930
C15—H150.930C17—H17A0.960
C8—C71.448 (3)C17—H17B0.960
C8—H80.930C17—H17C0.960
N1—C171.444 (3)C16—H16A0.960
N1—C161.450 (3)C16—H16B0.960
C12—C111.365 (3)C16—H16C0.960
C12—H120.930C1—H10.930
C6—C51.383 (3)
N1—C13—C14121.63 (18)C3—C4—C5118.8 (2)
N1—C13—C12121.38 (18)C3—C4—H4120.6
C14—C13—C12116.97 (18)C5—C4—H4120.6
C11—C10—C15116.45 (18)C12—C11—C10122.21 (19)
C11—C10—C9123.63 (19)C12—C11—H11118.9
C15—C10—C9119.89 (18)C10—C11—H11118.9
C8—C9—C10128.1 (2)O1—C7—C8121.3 (2)
C8—C9—H9116.0O1—C7—C6119.6 (2)
C10—C9—H9116.0C8—C7—C6119.03 (19)
C14—C15—C10122.09 (19)C4—C5—C6122.1 (2)
C14—C15—H15119.0C4—C5—Cl2117.72 (18)
C10—C15—H15119.0C6—C5—Cl2120.17 (18)
C9—C8—C7125.7 (2)C1—C2—C3118.9 (2)
C9—C8—H8117.2C1—C2—H2120.5
C7—C8—H8117.2C3—C2—H2120.5
C13—N1—C17121.42 (18)N1—C17—H17A109.5
C13—N1—C16120.27 (18)N1—C17—H17B109.5
C17—N1—C16117.56 (18)H17A—C17—H17B109.5
C11—C12—C13121.25 (19)N1—C17—H17C109.5
C11—C12—H12119.4H17A—C17—H17C109.5
C13—C12—H12119.4H17B—C17—H17C109.5
C5—C6—C1116.9 (2)N1—C16—H16A109.5
C5—C6—C7122.5 (2)N1—C16—H16B109.5
C1—C6—C7120.6 (2)H16A—C16—H16B109.5
C4—C3—C2121.1 (2)N1—C16—H16C109.5
C4—C3—Cl1119.27 (18)H16A—C16—H16C109.5
C2—C3—Cl1119.55 (19)H16B—C16—H16C109.5
C15—C14—C13120.99 (19)C2—C1—C6122.1 (2)
C15—C14—H14119.5C2—C1—H1118.9
C13—C14—H14119.5C6—C1—H1118.9
C11—C10—C9—C811.4 (4)C9—C10—C11—C12176.6 (2)
C15—C10—C9—C8−170.5 (2)C9—C8—C7—O1177.9 (2)
C11—C10—C15—C14−0.1 (3)C9—C8—C7—C6−0.9 (3)
C9—C10—C15—C14−178.3 (2)C5—C6—C7—O1−61.9 (3)
C10—C9—C8—C7−176.3 (2)C1—C6—C7—O1117.2 (3)
C14—C13—N1—C17−168.4 (2)C5—C6—C7—C8117.0 (2)
C12—C13—N1—C1713.1 (3)C1—C6—C7—C8−64.0 (3)
C14—C13—N1—C161.6 (3)C3—C4—C5—C6−2.3 (3)
C12—C13—N1—C16−177.0 (2)C3—C4—C5—Cl2179.29 (16)
N1—C13—C12—C11177.7 (2)C1—C6—C5—C41.5 (3)
C14—C13—C12—C11−0.9 (3)C7—C6—C5—C4−179.42 (19)
C10—C15—C14—C131.2 (3)C1—C6—C5—Cl2179.91 (16)
N1—C13—C14—C15−179.3 (2)C7—C6—C5—Cl2−1.0 (3)
C12—C13—C14—C15−0.7 (3)C4—C3—C2—C11.1 (3)
C2—C3—C4—C50.9 (3)Cl1—C3—C2—C1−176.93 (17)
Cl1—C3—C4—C5178.95 (16)C3—C2—C1—C6−1.9 (3)
C13—C12—C11—C102.1 (3)C5—C6—C1—C20.6 (3)
C15—C10—C11—C12−1.5 (3)C7—C6—C1—C2−178.5 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O1i0.932.553.252 (3)132
C4—H4···Cg1ii0.932.953.784 (3)150
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O1i0.932.553.252 (3)132
C4—H4···Cg1ii0.932.953.784 (3)150
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2.
Acknowledgements top

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the IRHPA-DST program at IISc.

references
References top

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Watkin, D. J., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.