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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1525.
Published online 2008 July 19. doi:  10.1107/S1600536808021910
PMCID: PMC2962150

(E)-3-(2-Chloro­phen­yl)-1-(3-methoxy­phen­yl)prop-2-en-1-one

Abstract

The title compound, C16H13ClO2, adopts an E configuration with respect to the double bond of the propenone unit. The two benzene rings are twisted slightly from each other, making a dihedral angle of 7.14 (5)°. The mol­ecules are arranged in stacks, in which adjacent mol­ecules are related by inversion symmetry and form π–π inter­actions with a centroid–centroid distance of 3.7098 (6) Å. C—H(...)O and C—H(...)π inter­actions are formed between neighbouring mol­ecules.

Related literature

For related literature, see: Chantrapromma et al. (2005 [triangle], 2006 [triangle]); Fun et al. (2006 [triangle]); Patil, Fun et al. (2007 [triangle]); Patil, Dharmaprakash et al. (2006 [triangle], 2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1525-scheme1.jpg

Experimental

Crystal data

  • C16H13ClO2
  • M r = 272.71
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1525-efi1.jpg
  • a = 7.7352 (2) Å
  • b = 8.1405 (2) Å
  • c = 10.7411 (2) Å
  • α = 87.392 (1)°
  • β = 82.147 (1)°
  • γ = 74.794 (1)°
  • V = 646.52 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.29 mm−1
  • T = 100.0 (1) K
  • 0.38 × 0.30 × 0.16 mm

Data collection

  • Bruker SMART APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.899, T max = 0.955
  • 17497 measured reflections
  • 4314 independent reflections
  • 3644 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.101
  • S = 1.06
  • 4314 reflections
  • 173 parameters
  • H-atom parameters constrained
  • Δρmax = 0.53 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808021910/bi2296sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021910/bi2296Isup2.hkl

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

Acknowledgments

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks the Universiti Sains Malaysia for a postdoctoral research fellowship. This work was also supported by the Department of Science and Technology (DST), Government of India (grant No. SR/S2/LOP-17/2006).

supplementary crystallographic information

Comment

As a part of our ongoing investigation of non-linear optical (NLO) compounds (Chantrapromma et al., 2005, 2006; Fun et al., 2006; Patil, Fun et al., 2007; Patil, Dharmaprakash et al., 2006, 2007), the title compound has recently been prepared in our laboratory and its crystal structure is presented here.

The molecule exhibits an E configuration with respect to the C7=C8 double bond, the torsion angle being C7—C8—C9—C10 = -166.3 (9)°. The dihedral angle between the two phenyl rings is 7.14 (5)°, indicating that they are slightly twisted from each other. The molecules are interconnected by weak C—H···O interactions and the packing is further consolidated by C–H···π and π–π interactions between the C1—C6 (centroid Cg1) and C10—C15 (centroid Cg2) rings: Cg1···Cg2i = 3.7098 (6) Å [symmetry code: (i) 2 - x, -y, -z].

Experimental

2-Chlorobenzaldehyde (0.01 mol, 1.13 g) in ethanol (20 ml) was mixed with 3-methoxyacetophenone (0.01 mol, 1.37 ml) in 20 ml ethanol and the mixture was treated with 10 ml of 10% sodium hydroxide solution and stirred at room temperature for 8 h. The precipitate obtained was poured into ice-cold water (500 ml) and left to stand for 5 h. The resulting crude solid was filtered, dried and recrystallized from N,N-dimethylformamide by slow evaporation.

Refinement

H atoms were positioned geometrically with C—H = 0.93Å or Cmethyl—H = 0.96 Å and refined using a riding model, with Uiso(H) = 1.2Ueq(C) or 1.5eq(Cmethyl). A rotating group model was used for the methyl groups.

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids for non-H atoms.
Fig. 2.
Crystal packing of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C16H13ClO2Z = 2
Mr = 272.71F000 = 284
Triclinic, P1Dx = 1.401 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 7.7352 (2) ÅCell parameters from 7792 reflections
b = 8.1405 (2) Åθ = 2.2–37.5º
c = 10.7411 (2) ŵ = 0.29 mm1
α = 87.392 (1)ºT = 100.0 (1) K
β = 82.147 (1)ºBlock, colourless
γ = 74.794 (1)º0.38 × 0.30 × 0.16 mm
V = 646.52 (3) Å3

Data collection

Bruker SMART APEXII CCD diffractometer4314 independent reflections
Radiation source: fine-focus sealed tube3644 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.025
T = 100(1) Kθmax = 31.7º
[var phi] and ω scansθmin = 2.6º
Absorption correction: multi-scan(SADABS; Bruker, 2005)h = −11→10
Tmin = 0.899, Tmax = 0.955k = −11→12
17497 measured reflectionsl = −15→15

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.101  w = 1/[σ2(Fo2) + (0.0513P)2 + 0.1689P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
4314 reflectionsΔρmax = 0.53 e Å3
173 parametersΔρmin = −0.23 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
Cl11.15204 (4)0.08594 (3)−0.41471 (2)0.02216 (8)
O10.78728 (11)0.44819 (10)−0.05788 (8)0.02200 (17)
O20.46589 (11)0.70028 (11)0.36344 (8)0.02281 (17)
C11.29054 (14)−0.01282 (13)−0.30363 (10)0.01529 (19)
C21.44112 (15)−0.14294 (13)−0.34590 (10)0.0184 (2)
H2A1.4678−0.1705−0.43070.022*
C31.55059 (15)−0.23075 (13)−0.25988 (11)0.0196 (2)
H3A1.6517−0.3178−0.28700.024*
C41.51011 (15)−0.18945 (13)−0.13323 (11)0.0189 (2)
H4A1.5830−0.2495−0.07550.023*
C51.36046 (14)−0.05817 (13)−0.09349 (10)0.0172 (2)
H5A1.3348−0.0311−0.00860.021*
C61.24650 (14)0.03518 (12)−0.17720 (10)0.01485 (19)
C71.09255 (14)0.17825 (13)−0.13473 (10)0.01589 (19)
H7A1.04070.2526−0.19570.019*
C81.02124 (15)0.20974 (13)−0.01471 (10)0.0173 (2)
H8A1.06670.13410.04770.021*
C90.87148 (14)0.36241 (13)0.02113 (10)0.01643 (19)
C100.82784 (14)0.40997 (13)0.15679 (10)0.01584 (19)
C110.94385 (16)0.34122 (14)0.24498 (11)0.0207 (2)
H11A1.05180.26040.22100.025*
C120.89719 (18)0.39431 (15)0.36938 (11)0.0248 (2)
H12A0.97480.34890.42840.030*
C130.73691 (17)0.51359 (14)0.40576 (11)0.0218 (2)
H13A0.70620.54740.48920.026*
C140.62110 (15)0.58335 (13)0.31749 (10)0.0173 (2)
C150.66548 (14)0.53249 (13)0.19298 (10)0.01602 (19)
H15A0.58820.57930.13410.019*
C160.34703 (16)0.78256 (16)0.27587 (12)0.0253 (2)
H16A0.24450.86190.31940.038*
H16B0.30700.69890.23550.038*
H16C0.40960.84230.21370.038*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.02040 (14)0.02714 (14)0.01654 (13)−0.00027 (10)−0.00537 (9)−0.00122 (9)
O10.0219 (4)0.0231 (4)0.0173 (4)0.0008 (3)−0.0021 (3)−0.0019 (3)
O20.0212 (4)0.0263 (4)0.0173 (4)−0.0009 (3)0.0018 (3)−0.0059 (3)
C10.0140 (4)0.0170 (4)0.0154 (4)−0.0045 (4)−0.0027 (4)−0.0004 (3)
C20.0166 (5)0.0204 (5)0.0177 (5)−0.0041 (4)−0.0005 (4)−0.0049 (4)
C30.0155 (5)0.0170 (4)0.0249 (5)−0.0014 (4)−0.0019 (4)−0.0049 (4)
C40.0168 (5)0.0179 (5)0.0223 (5)−0.0030 (4)−0.0061 (4)−0.0004 (4)
C50.0162 (5)0.0197 (5)0.0159 (5)−0.0044 (4)−0.0027 (4)−0.0019 (4)
C60.0129 (4)0.0159 (4)0.0162 (5)−0.0043 (3)−0.0014 (3)−0.0022 (3)
C70.0137 (4)0.0161 (4)0.0181 (5)−0.0038 (3)−0.0019 (4)−0.0023 (3)
C80.0173 (5)0.0150 (4)0.0184 (5)−0.0029 (4)0.0000 (4)−0.0006 (4)
C90.0152 (5)0.0162 (4)0.0176 (5)−0.0046 (4)0.0005 (4)−0.0023 (3)
C100.0168 (5)0.0158 (4)0.0154 (4)−0.0056 (4)−0.0005 (4)−0.0015 (3)
C110.0201 (5)0.0191 (5)0.0218 (5)−0.0019 (4)−0.0042 (4)−0.0028 (4)
C120.0303 (6)0.0228 (5)0.0204 (5)−0.0022 (5)−0.0100 (5)−0.0007 (4)
C130.0286 (6)0.0216 (5)0.0151 (5)−0.0058 (4)−0.0025 (4)−0.0027 (4)
C140.0185 (5)0.0166 (4)0.0168 (5)−0.0058 (4)0.0013 (4)−0.0028 (4)
C150.0163 (5)0.0172 (4)0.0150 (5)−0.0056 (4)−0.0009 (4)−0.0008 (3)
C160.0173 (5)0.0288 (6)0.0272 (6)−0.0010 (4)−0.0022 (4)−0.0070 (5)

Geometric parameters (Å, °)

Cl1—C11.7400 (11)C8—C91.4836 (15)
O1—C91.2208 (14)C8—H8A0.930
O2—C141.3684 (13)C9—C101.4952 (14)
O2—C161.4264 (15)C10—C111.3915 (15)
C1—C21.3917 (14)C10—C151.4028 (14)
C1—C61.4018 (14)C11—C121.3933 (16)
C2—C31.3849 (16)C11—H11A0.930
C2—H2A0.930C12—C131.3796 (17)
C3—C41.3899 (16)C12—H12A0.930
C3—H3A0.930C13—C141.3929 (16)
C4—C51.3863 (15)C13—H13A0.930
C4—H4A0.930C14—C151.3886 (14)
C5—C61.4021 (15)C15—H15A0.930
C5—H5A0.930C16—H16A0.960
C6—C71.4680 (14)C16—H16B0.960
C7—C81.3391 (15)C16—H16C0.960
C7—H7A0.930
C14—O2—C16117.57 (9)O1—C9—C10120.76 (10)
C2—C1—C6122.55 (10)C8—C9—C10118.14 (9)
C2—C1—Cl1116.93 (8)C11—C10—C15120.12 (10)
C6—C1—Cl1120.49 (8)C11—C10—C9122.44 (10)
C3—C2—C1119.02 (10)C15—C10—C9117.41 (9)
C3—C2—H2A120.5C10—C11—C12119.56 (10)
C1—C2—H2A120.5C10—C11—H11A120.2
C2—C3—C4120.35 (10)C12—C11—H11A120.2
C2—C3—H3A119.8C13—C12—C11120.58 (11)
C4—C3—H3A119.8C13—C12—H12A119.7
C5—C4—C3119.61 (10)C11—C12—H12A119.7
C5—C4—H4A120.2C12—C13—C14119.96 (10)
C3—C4—H4A120.2C12—C13—H13A120.0
C4—C5—C6122.09 (10)C14—C13—H13A120.0
C4—C5—H5A119.0O2—C14—C15124.45 (10)
C6—C5—H5A119.0O2—C14—C13115.23 (10)
C1—C6—C5116.37 (9)C15—C14—C13120.32 (10)
C1—C6—C7122.05 (9)C14—C15—C10119.46 (10)
C5—C6—C7121.56 (9)C14—C15—H15A120.3
C8—C7—C6124.89 (10)C10—C15—H15A120.3
C8—C7—H7A117.6O2—C16—H16A109.5
C6—C7—H7A117.6O2—C16—H16B109.5
C7—C8—C9121.58 (10)H16A—C16—H16B109.5
C7—C8—H8A119.2O2—C16—H16C109.5
C9—C8—H8A119.2H16A—C16—H16C109.5
O1—C9—C8121.09 (10)H16B—C16—H16C109.5
C6—C1—C2—C31.08 (15)O1—C9—C10—C11−164.94 (10)
Cl1—C1—C2—C3−176.96 (8)C8—C9—C10—C1114.25 (15)
C1—C2—C3—C40.12 (16)O1—C9—C10—C1513.15 (15)
C2—C3—C4—C5−0.79 (16)C8—C9—C10—C15−167.66 (9)
C3—C4—C5—C60.30 (16)C15—C10—C11—C120.30 (16)
C2—C1—C6—C5−1.52 (15)C9—C10—C11—C12178.33 (10)
Cl1—C1—C6—C5176.45 (7)C10—C11—C12—C130.30 (18)
C2—C1—C6—C7176.86 (9)C11—C12—C13—C14−0.69 (18)
Cl1—C1—C6—C7−5.17 (13)C16—O2—C14—C15−3.86 (15)
C4—C5—C6—C10.82 (15)C16—O2—C14—C13176.68 (10)
C4—C5—C6—C7−177.57 (10)C12—C13—C14—O2179.96 (10)
C1—C6—C7—C8165.91 (10)C12—C13—C14—C150.48 (17)
C5—C6—C7—C8−15.79 (15)O2—C14—C15—C10−179.32 (9)
C6—C7—C8—C9176.74 (9)C13—C14—C15—C100.11 (15)
C7—C8—C9—O112.94 (16)C11—C10—C15—C14−0.50 (15)
C7—C8—C9—C10−166.25 (9)C9—C10—C15—C14−178.64 (9)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2A···O2i0.932.503.3887 (13)161
C4—H4A···O1ii0.932.573.3003 (13)136
C16—H16B···O1iii0.962.583.4899 (14)158
C16—H16C···Cg1iv0.962.823.6137 (14)135

Symmetry codes: (i) x+1, y−1, z−1; (ii) x+1, y−1, z; (iii) −x+1, −y+1, −z; (iv) −x+2, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2296).

References

  • Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chantrapromma, S., Jindawong, B., Fun, H.-K., Anjum, S. & Karalai, C. (2005). Acta Cryst. E61, o2096–o2098.
  • Chantrapromma, S., Ruanwas, P., Jindawong, B., Razak, I. A. & Fun, H.-K. (2006). Acta Cryst. E62, o875–o877.
  • Fun, H.-K., Rodwatcharapiban, P., Jindawong, B. & Chantrapromma, S. (2006). Acta Cryst. E62, o2725–o2727.
  • Patil, P. S., Dharmaprakash, S. M., Fun, H.-K. & Karthikeyan, M. S. (2006). J. Cryst. Growth, 297, 111–116.
  • Patil, P. S., Dharmaprakash, S. M., Ramakrishna, K., Fun, H.-K., Sai Santosh Kumar, R. & Rao, D. N. (2007). J. Cryst. Growth, 303, 520–524.
  • Patil, P. S., Fun, H.-K., Chantrapromma, S. & Dharmaprakash, S. M. (2007). Acta Cryst. E63, o2497–o2498.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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