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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1626.
Published online 2008 July 31. doi:  10.1107/S1600536808023003
PMCID: PMC2962235

2,6-Bis(2,4-dichloro­benzyl­idene)cyclo­hexa­none

Abstract

The title compound, C20H14Cl4O, was prepared from a mixture of 2,4-dichloro­benzophenone and cyclo­hexa­none. The dihedral angles formed by the cyclohexane ring and two benzene rings are 39.18 (2) and 60.72 (2)°. There are some weak intra­molecular C—H(...)O and C—H(...)Cl hydrogen-bond contacts in the crystal structure.

Related literature

For related literature, see: Butcher et al. (2006 [triangle]); Deli et al. (1984 [triangle]); Jia et al. (1989 [triangle]); Yu et al. (2000 [triangle]).

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Object name is e-64-o1626-scheme1.jpg

Experimental

Crystal data

  • C20H14Cl4O
  • M r = 412.11
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1626-efi1.jpg
  • a = 14.469 (2) Å
  • b = 8.0602 (12) Å
  • c = 31.554 (4) Å
  • V = 3679.9 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.65 mm−1
  • T = 293 (2) K
  • 0.20 × 0.15 × 0.10 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1997 [triangle]) T min = 0.881, T max = 0.938
  • 21985 measured reflections
  • 4570 independent reflections
  • 2735 reflections with I > 2σ(I)
  • R int = 0.053

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.118
  • S = 1.03
  • 4570 reflections
  • 226 parameters
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.28 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.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808023003/at2592sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023003/at2592Isup2.hkl

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

Acknowledgments

The authors thank the National Science Foundation of Weifang University (grant: No.2008Z04).

supplementary crystallographic information

Comment

As useful precursors to potentially bioactive pyrimidine derivatives, a,a-bis(substituted benzylidene) cycloalkanones have attracted considerable attention for many years (Deli et al., 1984). In recent years, a series of non-linear optically active bis(benzylidene) ketones have been synthesized (Yu et al., 2000). As part of our search for new non-linear optically active compounds, we synthesized the title compound (I), and describe its structure here.

In the structure of (I) (Fig. 1), all of the bond lengthes and bond angles fall in the normal range (Yu et al., 2000; Jia et al., 1989; Butcher et al., 2006). There are some weak C—H···O and C—H···Cl intramolecular hydrogen bonds in the crystal structure.

Experimental

A mixture of the 2,4-dichlorobenzophenone (0.2 mol), and cyclohexanone (0.1 mol) and 10% NaOH (10 ml) was stirred in ethanol (30 mL) for 5 h to afford the title compound [yield: 82%]. Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Refinement

H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H = 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Crystal data

C20H14Cl4OZ = 8
Mr = 412.11F000 = 1680
Orthorhombic, PbcaDx = 1.488 Mg m3
Hall symbol: -P 2ac 2abMo Kα radiation λ = 0.71073 Å
a = 14.469 (2) ŵ = 0.65 mm1
b = 8.0602 (12) ÅT = 293 (2) K
c = 31.554 (4) ÅBar, yellow
V = 3679.9 (9) Å30.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer4570 independent reflections
Radiation source: fine-focus sealed tube2735 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.053
T = 293(2) Kθmax = 28.4º
[var phi] and ω scansθmin = 1.3º
Absorption correction: multi-scan(SADABS; Bruker, 1997)h = −19→18
Tmin = 0.881, Tmax = 0.938k = −10→10
21985 measured reflectionsl = −19→42

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.118  w = 1/[σ2(Fo2) + (0.0381P)2 + 1.6278P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
4570 reflectionsΔρmax = 0.24 e Å3
226 parametersΔρmin = −0.28 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
Cl1−0.37152 (7)0.07869 (15)−0.49524 (3)0.1044 (4)
Cl2−0.51233 (4)0.04759 (9)−0.33808 (2)0.05594 (19)
Cl30.06595 (6)0.60906 (12)−0.04572 (3)0.0852 (3)
Cl4−0.21635 (6)0.20911 (12)−0.08713 (2)0.0825 (3)
O1−0.36351 (10)0.3253 (2)−0.22630 (5)0.0557 (5)
C1−0.42738 (15)0.1234 (3)−0.37207 (8)0.0468 (6)
C2−0.43315 (18)0.0787 (4)−0.41435 (8)0.0578 (7)
H2A−0.48040.0098−0.42380.069*
C3−0.36783 (19)0.1381 (4)−0.44228 (9)0.0635 (8)
C4−0.29917 (19)0.2442 (4)−0.42879 (9)0.0663 (8)
H4A−0.25720.2881−0.44810.080*
C5−0.29343 (17)0.2844 (4)−0.38653 (9)0.0592 (7)
H5A−0.24650.3550−0.37760.071*
C6−0.35581 (16)0.2229 (3)−0.35643 (8)0.0466 (6)
C7−0.34846 (15)0.2620 (3)−0.31106 (8)0.0461 (6)
H7A−0.40410.2752−0.29670.055*
C8−0.27162 (14)0.2811 (3)−0.28761 (8)0.0419 (6)
C9−0.17413 (14)0.2600 (3)−0.30424 (8)0.0499 (6)
H9A−0.15710.3581−0.32020.060*
H9B−0.17270.1661−0.32350.060*
C10−0.10328 (15)0.2324 (3)−0.26939 (8)0.0502 (6)
H10A−0.11420.1261−0.25590.060*
H10B−0.04170.2310−0.28150.060*
C11−0.11002 (15)0.3693 (3)−0.23677 (8)0.0457 (6)
H11A−0.06120.3563−0.21600.055*
H11B−0.10200.4760−0.25050.055*
C12−0.20266 (14)0.3642 (3)−0.21491 (8)0.0412 (5)
C13−0.28552 (15)0.3230 (3)−0.24158 (7)0.0423 (6)
C14−0.21556 (16)0.3858 (3)−0.17333 (8)0.0466 (6)
H14A−0.27510.3680−0.16320.056*
C15−0.14545 (15)0.4349 (3)−0.14198 (8)0.0443 (6)
C16−0.08247 (16)0.5614 (3)−0.15088 (8)0.0512 (6)
H16A−0.08400.6112−0.17750.061*
C17−0.01834 (18)0.6150 (3)−0.12186 (8)0.0554 (7)
H17A0.02270.6995−0.12880.067*
C18−0.01524 (17)0.5426 (3)−0.08242 (8)0.0539 (7)
C19−0.07653 (18)0.4177 (3)−0.07173 (8)0.0555 (7)
H19A−0.07460.3691−0.04500.067*
C20−0.14056 (17)0.3665 (3)−0.10137 (8)0.0490 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.1071 (7)0.1580 (10)0.0482 (5)−0.0068 (7)0.0000 (5)−0.0108 (5)
Cl20.0381 (3)0.0687 (4)0.0610 (4)−0.0027 (3)0.0010 (3)0.0002 (3)
Cl30.0747 (5)0.1149 (7)0.0660 (5)−0.0291 (5)−0.0131 (4)−0.0144 (5)
Cl40.0959 (6)0.0945 (6)0.0572 (5)−0.0482 (5)−0.0024 (4)0.0122 (4)
O10.0313 (9)0.0847 (14)0.0509 (10)−0.0009 (8)0.0073 (8)0.0041 (10)
C10.0355 (13)0.0554 (16)0.0497 (15)0.0080 (11)−0.0013 (11)0.0045 (12)
C20.0506 (16)0.0682 (19)0.0546 (17)0.0054 (13)−0.0080 (13)−0.0023 (14)
C30.0559 (17)0.090 (2)0.0445 (15)0.0099 (16)−0.0043 (14)−0.0017 (15)
C40.0524 (16)0.093 (2)0.0531 (17)0.0033 (16)0.0063 (14)0.0141 (16)
C50.0459 (15)0.077 (2)0.0549 (17)−0.0076 (13)−0.0001 (13)0.0080 (15)
C60.0355 (12)0.0555 (15)0.0488 (15)0.0069 (11)−0.0019 (11)0.0027 (12)
C70.0335 (12)0.0547 (15)0.0501 (15)0.0002 (10)0.0026 (11)0.0034 (12)
C80.0331 (12)0.0459 (14)0.0468 (14)−0.0012 (10)0.0041 (10)0.0056 (11)
C90.0331 (12)0.0648 (17)0.0517 (15)−0.0026 (11)0.0061 (11)−0.0020 (13)
C100.0318 (12)0.0576 (16)0.0612 (16)0.0049 (11)0.0045 (12)−0.0007 (13)
C110.0316 (12)0.0537 (15)0.0518 (15)−0.0006 (11)−0.0006 (11)0.0023 (12)
C120.0327 (12)0.0436 (14)0.0473 (14)0.0007 (10)0.0024 (11)0.0048 (11)
C130.0331 (12)0.0458 (14)0.0481 (14)0.0018 (10)0.0034 (11)0.0096 (11)
C140.0340 (12)0.0552 (15)0.0507 (15)−0.0003 (11)0.0016 (11)0.0050 (12)
C150.0370 (12)0.0527 (15)0.0431 (14)0.0021 (11)0.0027 (11)−0.0019 (12)
C160.0490 (14)0.0575 (16)0.0471 (15)−0.0007 (12)0.0020 (12)0.0047 (13)
C170.0513 (15)0.0566 (17)0.0583 (17)−0.0101 (13)0.0042 (13)−0.0005 (14)
C180.0484 (14)0.0633 (17)0.0499 (16)−0.0018 (13)−0.0033 (12)−0.0111 (14)
C190.0629 (17)0.0642 (18)0.0393 (14)−0.0059 (14)−0.0008 (12)−0.0001 (13)
C200.0487 (14)0.0513 (16)0.0469 (15)−0.0062 (12)0.0052 (12)−0.0013 (12)

Geometric parameters (Å, °)

Cl1—C31.739 (3)C9—H9B0.9700
Cl2—C11.742 (2)C10—C111.512 (3)
Cl3—C181.735 (3)C10—H10A0.9700
Cl4—C201.736 (3)C10—H10B0.9700
O1—C131.227 (2)C11—C121.508 (3)
C1—C21.384 (3)C11—H11A0.9700
C1—C61.400 (3)C11—H11B0.9700
C2—C31.378 (4)C12—C141.337 (3)
C2—H2A0.9300C12—C131.502 (3)
C3—C41.378 (4)C14—C151.471 (3)
C4—C51.375 (4)C14—H14A0.9300
C4—H4A0.9300C15—C161.396 (3)
C5—C61.401 (3)C15—C201.397 (3)
C5—H5A0.9300C16—C171.373 (3)
C6—C71.470 (3)C16—H16A0.9300
C7—C81.345 (3)C17—C181.375 (4)
C7—H7A0.9300C17—H17A0.9300
C8—C131.504 (3)C18—C191.383 (4)
C8—C91.515 (3)C19—C201.380 (3)
C9—C101.520 (3)C19—H19A0.9300
C9—H9A0.9700
C2—C1—C6122.2 (2)H10A—C10—H10B108.2
C2—C1—Cl2117.4 (2)C12—C11—C10110.4 (2)
C6—C1—Cl2120.4 (2)C12—C11—H11A109.6
C3—C2—C1119.0 (3)C10—C11—H11A109.6
C3—C2—H2A120.5C12—C11—H11B109.6
C1—C2—H2A120.5C10—C11—H11B109.6
C2—C3—C4120.8 (3)H11A—C11—H11B108.1
C2—C3—Cl1119.9 (2)C14—C12—C13117.9 (2)
C4—C3—Cl1119.3 (2)C14—C12—C11124.7 (2)
C5—C4—C3119.3 (3)C13—C12—C11117.3 (2)
C5—C4—H4A120.3O1—C13—C12120.7 (2)
C3—C4—H4A120.3O1—C13—C8120.4 (2)
C4—C5—C6122.4 (3)C12—C13—C8118.93 (19)
C4—C5—H5A118.8C12—C14—C15126.8 (2)
C6—C5—H5A118.8C12—C14—H14A116.6
C1—C6—C5116.1 (2)C15—C14—H14A116.6
C1—C6—C7121.3 (2)C16—C15—C20116.1 (2)
C5—C6—C7122.5 (2)C16—C15—C14120.7 (2)
C8—C7—C6128.4 (2)C20—C15—C14123.1 (2)
C8—C7—H7A115.8C17—C16—C15122.5 (2)
C6—C7—H7A115.8C17—C16—H16A118.8
C7—C8—C13116.5 (2)C15—C16—H16A118.8
C7—C8—C9124.5 (2)C16—C17—C18119.5 (2)
C13—C8—C9118.96 (19)C16—C17—H17A120.3
C8—C9—C10113.2 (2)C18—C17—H17A120.3
C8—C9—H9A108.9C17—C18—C19120.6 (2)
C10—C9—H9A108.9C17—C18—Cl3119.7 (2)
C8—C9—H9B108.9C19—C18—Cl3119.8 (2)
C10—C9—H9B108.9C20—C19—C18118.9 (2)
H9A—C9—H9B107.8C20—C19—H19A120.6
C11—C10—C9110.0 (2)C18—C19—H19A120.6
C11—C10—H10A109.7C19—C20—C15122.5 (2)
C9—C10—H10A109.7C19—C20—Cl4117.9 (2)
C11—C10—H10B109.7C15—C20—Cl4119.59 (19)
C9—C10—H10B109.7
C6—C1—C2—C3−1.9 (4)C11—C12—C13—O1−176.1 (2)
Cl2—C1—C2—C3179.2 (2)C14—C12—C13—C8−173.9 (2)
C1—C2—C3—C4−1.9 (4)C11—C12—C13—C83.0 (3)
C1—C2—C3—Cl1178.0 (2)C7—C8—C13—O15.7 (3)
C2—C3—C4—C53.2 (4)C9—C8—C13—O1−173.0 (2)
Cl1—C3—C4—C5−176.7 (2)C7—C8—C13—C12−173.4 (2)
C3—C4—C5—C6−0.8 (4)C9—C8—C13—C127.9 (3)
C2—C1—C6—C54.1 (4)C13—C12—C14—C15−176.6 (2)
Cl2—C1—C6—C5−176.99 (19)C11—C12—C14—C156.7 (4)
C2—C1—C6—C7−176.9 (2)C12—C14—C15—C1643.5 (4)
Cl2—C1—C6—C71.9 (3)C12—C14—C15—C20−140.1 (3)
C4—C5—C6—C1−2.8 (4)C20—C15—C16—C170.8 (4)
C4—C5—C6—C7178.3 (3)C14—C15—C16—C17177.5 (2)
C1—C6—C7—C8145.0 (3)C15—C16—C17—C180.0 (4)
C5—C6—C7—C8−36.1 (4)C16—C17—C18—C19−0.5 (4)
C6—C7—C8—C13179.4 (2)C16—C17—C18—Cl3179.7 (2)
C6—C7—C8—C9−2.0 (4)C17—C18—C19—C200.3 (4)
C7—C8—C9—C10−161.0 (2)Cl3—C18—C19—C20−180.0 (2)
C13—C8—C9—C1017.6 (3)C18—C19—C20—C150.6 (4)
C8—C9—C10—C11−53.5 (3)C18—C19—C20—Cl4179.8 (2)
C9—C10—C11—C1264.1 (3)C16—C15—C20—C19−1.1 (4)
C10—C11—C12—C14138.1 (3)C14—C15—C20—C19−177.7 (2)
C10—C11—C12—C13−38.5 (3)C16—C15—C20—Cl4179.69 (18)
C14—C12—C13—O17.0 (4)C14—C15—C20—Cl43.1 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C7—H7A···Cl20.932.743.055 (2)101
C7—H7A···O10.932.332.732 (3)105
C14—H14A···O10.932.392.759 (3)103

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2592).

References

  • Bruker (1997). SADABS, SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Butcher, R. J., Yathirajan, H. S., Sarojini, B. K., Narayana, B. & Indira, J. (2006). Acta Cryst. E62, o1910–o1912.
  • Deli, J., Lorand, T., Szabo, D. & Foldesi, A. (1984). Pharmazie, 39, 539–544. [PubMed]
  • Jia, Z., Quail, J. W., Arora, V. K. & Dimmock, J. R. (1989). Acta Cryst. C45, 285–289.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Yu, R. C., Yakimansky, A. V., Kothe, H., Voigt-Martin, I. G., Schollmeyer, D., Jansen, J., Zandbergen, H. & Tenkovtsev, A. V. (2000). Acta Cryst. A56, 436–450. [PubMed]

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