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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2009 May 14;65(Pt 6):o1266. doi: 10.1107/S1600536809015177

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

Navin N Bappalige a, Brinda b,*, Y Narayana a, V Upadyaya c
PMCID: PMC2969683  PMID: 21583130

Abstract

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⋯π inter­actions are formed between mol­ecules.

Related literature

For related structures, see: Murafuji et al. (1999 ▶); Liu et al. (2002 ▶); Patil et al. (2007a ▶,b ▶); Rosli et al. (2007 ▶).graphic file with name e-65-o1266-scheme1.jpg

Experimental

Crystal data

  • C17H15Cl2NO

  • M r = 320.20

  • Monoclinic, Inline graphic

  • a = 8.5741 (19) Å

  • b = 12.706 (3) Å

  • c = 14.671 (3) Å

  • β = 102.645 (4)°

  • V = 1559.5 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.41 mm−1

  • T = 290 K

  • 0.25 × 0.15 × 0.07 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.923, T max = 0.972

  • 11540 measured reflections

  • 2908 independent reflections

  • 2039 reflections with I > 2σ(I)

  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042

  • wR(F 2) = 0.106

  • S = 1.03

  • 2908 reflections

  • 192 parameters

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015177/bi2360sup1.cif

e-65-o1266-sup1.cif (18.2KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015177/bi2360Isup2.hkl

e-65-o1266-Isup2.hkl (139.8KB, hkl)

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C12—H12⋯O1i 0.93 2.55 3.252 (3) 132
C4—H4⋯Cg1ii 0.93 2.95 3.784 (3) 150
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Symmetry codes: (i) Inline graphic; (ii) Inline graphic. Cg1 is the centroid of the C10–C15 ring.

Acknowledgments

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

supplementary crystallographic information

Experimental

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

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).

Figures

Fig. 1.

Fig. 1.

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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.

Fig. 2.

Fig. 2.

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Packing diagram. The dotted lines indicate intermolecular C—H···O and C—H···π interactions.

Crystal data

C17H15Cl2NO F(000) = 664
Mr = 320.20 Dx = 1.364 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc Cell parameters from 3980 reflections
a = 8.5741 (19) Å θ = 2.0–26.0°
b = 12.706 (3) Å µ = 0.41 mm−1
c = 14.671 (3) Å T = 290 K
β = 102.645 (4)° Block, orange
V = 1559.5 (6) Å3 0.25 × 0.15 × 0.07 mm
Z = 4
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Data collection

Bruker SMART APEX CCD area-detector diffractometer 2908 independent reflections
Radiation source: fine-focus sealed tube 2039 reflections with I > 2σ(I)
graphite Rint = 0.031
φ and ω scans θmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −10→10
Tmin = 0.923, Tmax = 0.972 k = −15→15
11540 measured reflections l = −16→17
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Refinement

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)] = 0.042 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106 H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0505P)2 + 0.1972P] where P = (Fo2 + 2Fc2)/3
2908 reflections (Δ/σ)max < 0.001
192 parameters Δρmax = 0.20 e Å−3
0 restraints Δρmin = −0.17 e Å−3
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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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
Cl1 0.42606 (8) −0.03118 (5) 0.21634 (5) 0.0704 (2)
Cl2 0.33039 (10) 0.29372 (6) 0.42942 (5) 0.0851 (3)
C13 0.2618 (2) 0.71607 (15) −0.03057 (14) 0.0421 (5)
C10 0.1972 (2) 0.54646 (15) 0.08139 (14) 0.0414 (5)
C9 0.1721 (2) 0.45849 (17) 0.13874 (15) 0.0461 (5)
H9 0.2244 0.3964 0.1299 0.055*
C15 0.2754 (2) 0.53119 (16) 0.00809 (15) 0.0459 (5)
H15 0.3078 0.4636 −0.0037 0.055*
C8 0.0829 (3) 0.45512 (17) 0.20297 (16) 0.0508 (6)
H8 0.0247 0.5151 0.2101 0.061*
N1 0.2898 (2) 0.79802 (13) −0.08543 (13) 0.0518 (5)
C12 0.1844 (3) 0.73163 (16) 0.04341 (14) 0.0481 (5)
H12 0.1548 0.7993 0.0568 0.058*
C6 0.1595 (2) 0.26655 (16) 0.25224 (16) 0.0469 (5)
C3 0.3204 (3) 0.08209 (17) 0.23089 (17) 0.0509 (6)
C14 0.3057 (2) 0.61262 (16) −0.04685 (14) 0.0456 (5)
H14 0.3561 0.599 −0.0957 0.055*
C4 0.3608 (3) 0.13662 (17) 0.31339 (16) 0.0519 (6)
H4 0.4425 0.1129 0.3616 0.062*
C11 0.1517 (2) 0.64926 (17) 0.09597 (15) 0.0476 (5)
H11 0.0972 0.6622 0.1431 0.057*
C7 0.0693 (3) 0.36611 (18) 0.26236 (17) 0.0547 (6)
O1 −0.0115 (2) 0.37083 (15) 0.32101 (14) 0.0849 (6)
C5 0.2780 (3) 0.22710 (17) 0.32357 (15) 0.0501 (5)
C2 0.2015 (3) 0.11710 (19) 0.15886 (17) 0.0576 (6)
H2 0.1737 0.079 0.1036 0.069*
C17 0.2722 (3) 0.90604 (18) −0.05879 (18) 0.0685 (7)
H17A 0.1625 0.9193 −0.0574 0.103*
H17B 0.304 0.9521 −0.1033 0.103*
H17C 0.3383 0.9185 0.0021 0.103*
C16 0.3630 (3) 0.77905 (19) −0.16414 (17) 0.0665 (7)
H16A 0.4725 0.7587 −0.1417 0.1*
H16B 0.3584 0.8422 −0.2006 0.1*
H16C 0.3064 0.7238 −0.2022 0.1*
C1 0.1244 (3) 0.20911 (18) 0.16968 (17) 0.0577 (6)
H1 0.046 0.2339 0.1202 0.069*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Cl1 0.0823 (5) 0.0539 (4) 0.0800 (5) 0.0084 (3) 0.0288 (4) 0.0038 (3)
Cl2 0.1090 (6) 0.0798 (5) 0.0577 (4) 0.0164 (4) −0.0008 (4) −0.0118 (3)
C13 0.0447 (12) 0.0425 (12) 0.0377 (11) −0.0018 (9) 0.0062 (9) 0.0013 (9)
C10 0.0437 (11) 0.0407 (12) 0.0406 (12) 0.0008 (9) 0.0110 (10) 0.0024 (9)
C9 0.0442 (12) 0.0439 (12) 0.0499 (13) 0.0026 (9) 0.0098 (10) 0.0023 (10)
C15 0.0531 (13) 0.0363 (11) 0.0508 (13) 0.0034 (10) 0.0166 (11) −0.0031 (10)
C8 0.0476 (12) 0.0472 (13) 0.0604 (15) 0.0057 (10) 0.0178 (11) 0.0116 (11)
N1 0.0671 (12) 0.0415 (10) 0.0496 (11) −0.0017 (9) 0.0187 (9) 0.0063 (8)
C12 0.0629 (14) 0.0365 (11) 0.0466 (13) 0.0078 (10) 0.0158 (11) 0.0002 (9)
C6 0.0451 (12) 0.0426 (12) 0.0546 (14) −0.0054 (10) 0.0142 (11) 0.0104 (10)
C3 0.0543 (14) 0.0443 (13) 0.0585 (15) −0.0036 (10) 0.0219 (12) 0.0083 (11)
C14 0.0524 (13) 0.0448 (12) 0.0430 (12) 0.0010 (10) 0.0176 (10) −0.0010 (10)
C4 0.0545 (13) 0.0502 (13) 0.0496 (14) 0.0017 (11) 0.0081 (11) 0.0124 (11)
C11 0.0556 (13) 0.0496 (13) 0.0413 (12) 0.0050 (10) 0.0189 (10) 0.0009 (10)
C7 0.0451 (12) 0.0573 (14) 0.0645 (15) −0.0020 (11) 0.0181 (12) 0.0118 (12)
O1 0.0906 (13) 0.0778 (13) 0.1068 (15) 0.0194 (10) 0.0665 (12) 0.0326 (11)
C5 0.0550 (13) 0.0484 (13) 0.0480 (13) −0.0035 (11) 0.0135 (11) 0.0069 (10)
C2 0.0610 (15) 0.0550 (15) 0.0539 (14) −0.0095 (12) 0.0061 (12) −0.0027 (11)
C17 0.0926 (19) 0.0432 (14) 0.0702 (17) −0.0039 (13) 0.0186 (15) 0.0076 (12)
C16 0.0852 (18) 0.0624 (16) 0.0571 (15) −0.0086 (13) 0.0268 (14) 0.0111 (12)
C1 0.0508 (13) 0.0598 (15) 0.0562 (15) −0.0032 (12) −0.0019 (11) 0.0079 (12)
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Geometric parameters (Å, °)

Cl1—C3 1.738 (2) C6—C1 1.389 (3)
Cl2—C5 1.739 (2) C6—C7 1.507 (3)
C13—N1 1.369 (2) C3—C4 1.372 (3)
C13—C14 1.402 (3) C3—C2 1.372 (3)
C13—C12 1.405 (3) C14—H14 0.930
C10—C11 1.393 (3) C4—C5 1.376 (3)
C10—C15 1.400 (3) C4—H4 0.9300
C10—C9 1.443 (3) C11—H11 0.930
C9—C8 1.338 (3) C7—O1 1.218 (3)
C9—H9 0.930 C2—C1 1.369 (3)
C15—C14 1.371 (3) C2—H2 0.930
C15—H15 0.930 C17—H17A 0.960
C8—C7 1.448 (3) C17—H17B 0.960
C8—H8 0.930 C17—H17C 0.960
N1—C17 1.444 (3) C16—H16A 0.960
N1—C16 1.450 (3) C16—H16B 0.960
C12—C11 1.365 (3) C16—H16C 0.960
C12—H12 0.930 C1—H1 0.930
C6—C5 1.383 (3)
N1—C13—C14 121.63 (18) C3—C4—C5 118.8 (2)
N1—C13—C12 121.38 (18) C3—C4—H4 120.6
C14—C13—C12 116.97 (18) C5—C4—H4 120.6
C11—C10—C15 116.45 (18) C12—C11—C10 122.21 (19)
C11—C10—C9 123.63 (19) C12—C11—H11 118.9
C15—C10—C9 119.89 (18) C10—C11—H11 118.9
C8—C9—C10 128.1 (2) O1—C7—C8 121.3 (2)
C8—C9—H9 116.0 O1—C7—C6 119.6 (2)
C10—C9—H9 116.0 C8—C7—C6 119.03 (19)
C14—C15—C10 122.09 (19) C4—C5—C6 122.1 (2)
C14—C15—H15 119.0 C4—C5—Cl2 117.72 (18)
C10—C15—H15 119.0 C6—C5—Cl2 120.17 (18)
C9—C8—C7 125.7 (2) C1—C2—C3 118.9 (2)
C9—C8—H8 117.2 C1—C2—H2 120.5
C7—C8—H8 117.2 C3—C2—H2 120.5
C13—N1—C17 121.42 (18) N1—C17—H17A 109.5
C13—N1—C16 120.27 (18) N1—C17—H17B 109.5
C17—N1—C16 117.56 (18) H17A—C17—H17B 109.5
C11—C12—C13 121.25 (19) N1—C17—H17C 109.5
C11—C12—H12 119.4 H17A—C17—H17C 109.5
C13—C12—H12 119.4 H17B—C17—H17C 109.5
C5—C6—C1 116.9 (2) N1—C16—H16A 109.5
C5—C6—C7 122.5 (2) N1—C16—H16B 109.5
C1—C6—C7 120.6 (2) H16A—C16—H16B 109.5
C4—C3—C2 121.1 (2) N1—C16—H16C 109.5
C4—C3—Cl1 119.27 (18) H16A—C16—H16C 109.5
C2—C3—Cl1 119.55 (19) H16B—C16—H16C 109.5
C15—C14—C13 120.99 (19) C2—C1—C6 122.1 (2)
C15—C14—H14 119.5 C2—C1—H1 118.9
C13—C14—H14 119.5 C6—C1—H1 118.9
C11—C10—C9—C8 11.4 (4) C9—C10—C11—C12 176.6 (2)
C15—C10—C9—C8 −170.5 (2) C9—C8—C7—O1 177.9 (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—O1 117.2 (3)
C14—C13—N1—C17 −168.4 (2) C5—C6—C7—C8 117.0 (2)
C12—C13—N1—C17 13.1 (3) C1—C6—C7—C8 −64.0 (3)
C14—C13—N1—C16 1.6 (3) C3—C4—C5—C6 −2.3 (3)
C12—C13—N1—C16 −177.0 (2) C3—C4—C5—Cl2 179.29 (16)
N1—C13—C12—C11 177.7 (2) C1—C6—C5—C4 1.5 (3)
C14—C13—C12—C11 −0.9 (3) C7—C6—C5—C4 −179.42 (19)
C10—C15—C14—C13 1.2 (3) C1—C6—C5—Cl2 179.91 (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—C1 1.1 (3)
C2—C3—C4—C5 0.9 (3) Cl1—C3—C2—C1 −176.93 (17)
Cl1—C3—C4—C5 178.95 (16) C3—C2—C1—C6 −1.9 (3)
C13—C12—C11—C10 2.1 (3) C5—C6—C1—C2 0.6 (3)
C15—C10—C11—C12 −1.5 (3) C7—C6—C1—C2 −178.5 (2)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
C12—H12···O1i 0.93 2.55 3.252 (3) 132
C4—H4···Cg1ii 0.93 2.95 3.784 (3) 150
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Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2360).

References

  1. Bruker (2004). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  2. Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  3. Liu, Z.-Q., Fang, Q., Yu, W.-T., Xue, G., Cao, D.-X. & Jiang, M.-H. (2002). Acta Cryst. C58, o445–o446. [DOI] [PubMed]
  4. Murafuji, T., Sugihara, Y., Moriya, T., Mikata, Y. & Yan, S. (1999). New J. Chem 23, 683–685.
  5. Patil, P. S., Chantrapromma, S., Fun, H.-K. & Dharmaprakash, S. M. (2007a). Acta Cryst. E63, o1738–o1740.
  6. Patil, P. S., Chantrapromma, S., Fun, H.-K. & Dharmaprakash, S. M. (2007b). Acta Cryst. E63, o3253–o3254.
  7. Rosli, M. M., Patil, P. S., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2007). Acta Cryst. E63, o2692.
  8. Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  9. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  10. Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]
  11. Watkin, D. J., Pearce, L. & Prout, C. K. (1993). CAMERON Chemical Crystallography Laboratory, University of Oxford, England.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015177/bi2360sup1.cif

e-65-o1266-sup1.cif (18.2KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015177/bi2360Isup2.hkl

e-65-o1266-Isup2.hkl (139.8KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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