PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1266.
Published online 2009 May 14. doi:  10.1107/S1600536809015177
PMCID: PMC2969683

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

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 [triangle]); Liu et al. (2002 [triangle]); Patil et al. (2007a [triangle],b [triangle]); Rosli et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1266-scheme1.jpg

Experimental

Crystal data

  • C17H15Cl2NO
  • M r = 320.20
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1266-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT (Bruker, 2004 [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: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and CAMERON (Watkin et al., 1993 [triangle]); software used to prepare material for publication: PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

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

Crystal data

C17H15Cl2NOF(000) = 664
Mr = 320.20Dx = 1.364 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3980 reflections
a = 8.5741 (19) Åθ = 2.0–26.0°
b = 12.706 (3) ŵ = 0.41 mm1
c = 14.671 (3) ÅT = 290 K
β = 102.645 (4)°Block, orange
V = 1559.5 (6) Å30.25 × 0.15 × 0.07 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer2908 independent reflections
Radiation source: fine-focus sealed tube2039 reflections with I > 2σ(I)
graphiteRint = 0.031
[var phi] and ω scansθmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.923, Tmax = 0.972k = −15→15
11540 measured reflectionsl = −16→17

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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0505P)2 + 0.1972P] where P = (Fo2 + 2Fc2)/3
2908 reflections(Δ/σ)max < 0.001
192 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = −0.17 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
Cl10.42606 (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)

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, °)

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, °)

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.

Footnotes

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

References

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

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