Acta Cryst. (2007). E63, o3702 [ doi:10.1107/S1600536807037634 ]
In the centrosymmetric title compound, C24H16Cl2O2, the dihedral angle between the central and terminal benzene rings is 46.27 (9)°. Edge-to-face C-H
![[pi]](http://journals.iucr.org/logos/entities/pi_rmgif.gif)
interactions are observed, with Hcentroid distances in the range 2.70-2.83 Å. ClCl contacts of 3.3701 (14) Å are also present.
A mixture of methanol (25 ml) and 10% aqueous NaOH (5 ml) solution were taken in a conical flask. A previously prepared small portion of terephthalaldehyde (0.001 mol) and 1-(4-chlorophenyl)ethanone (0.002 mol) dissolved in methanol was added to the conical flask with stirring and the temperature of the solution was maintained between 298 and 303 K. A precipitate was obtained after stirring the solution for about five minutes. The remaining portion of the aldehyde and ketone mixture was added and the solution was stirred for a further 60 minutes. The separated product was filtered, washed with water and dried. The resulting compound was purified by recrystallization from DMF. Single crystals used for X-ray diffraction analysis were grown by slow evaporation of a DMF solution.
H atoms were placed in calculated positions (C—H = 0.95 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).
Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997), and SORTAV (Blessing, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.
![[Figure 1]](./bi2226fig1thm.gif)
| Fig. 1. The molecular structure of the title compound showing 50% displacement ellipsoids (H atoms are drawn as spheres of arbitrary radius). Symmetry code: (i) −x, 1 − y, −z. |
![[Figure 2]](./bi2226fig2thm.gif)
| Fig. 2. Partial packing diagram showing the C—H···π interactions as dashed lines. |
![[Figure 3]](./bi2226fig3thm.gif)
| Fig. 3. Unit-cell packing viewed down [010] with H atoms omitted for clarity. |
| C24H16Cl2O2 | F000 = 420 |
| Mr = 407.26 | Dx = 1.438 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 8003 reflections |
| a = 22.9779 (19) Å | θ = 2.9–27.5º |
| b = 7.0369 (5) Å | µ = 0.36 mm−1 |
| c = 5.8425 (5) Å | T = 120 (2) K |
| β = 95.229 (3)º | Plate, pale yellow |
| V = 940.76 (13) Å3 | 0.24 × 0.12 × 0.02 mm |
| Z = 2 |
| Nonius KappaCCD area-detector diffractometer | 1739 independent reflections |
| Radiation source: fine-focus sealed tube | 1556 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.035 |
| T = 120(2) K | θmax = 26.0º |
| ω and φ scans | θmin = 3.0º |
| Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −28→28 |
| Tmin = 0.918, Tmax = 0.993 | k = −8→8 |
| 6340 measured reflections | l = −7→7 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.061 | H-atom parameters constrained |
| wR(F2) = 0.200 | w = 1/[σ2(Fo2) + (0.0964P)2 + 1.6678P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.16 | (Δ/σ)max < 0.001 |
| 1739 reflections | Δρmax = 0.43 e Å−3 |
| 127 parameters | Δρmin = −0.45 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C24H16Cl2O2 | V = 940.76 (13) Å3 |
| Mr = 407.26 | Z = 2 |
| Monoclinic, P21/c | Mo Kα |
| a = 22.9779 (19) Å | µ = 0.36 mm−1 |
| b = 7.0369 (5) Å | T = 120 (2) K |
| c = 5.8425 (5) Å | 0.24 × 0.12 × 0.02 mm |
| β = 95.229 (3)º |
| Nonius KappaCCD area-detector diffractometer | 1739 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2003) | 1556 reflections with I > 2σ(I) |
| Tmin = 0.918, Tmax = 0.993 | Rint = 0.035 |
| 6340 measured reflections |
| R[F2 > 2σ(F2)] = 0.061 | 127 parameters |
| wR(F2) = 0.200 | H-atom parameters constrained |
| S = 1.16 | Δρmax = 0.43 e Å−3 |
| 1739 reflections | Δρmin = −0.45 e Å−3 |
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 > 2sigma(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. |
| x | y | z | Uiso*/Ueq | ||
| C1 | −0.00124 (14) | 0.4218 (4) | 0.2158 (5) | 0.0217 (7) | |
| H1 | −0.0022 | 0.3663 | 0.3636 | 0.026* | |
| C2 | 0.05237 (13) | 0.4808 (4) | 0.1436 (5) | 0.0200 (7) | |
| C3 | 0.05293 (14) | 0.5572 (4) | −0.0756 (6) | 0.0220 (7) | |
| H3 | 0.0889 | 0.5952 | −0.1298 | 0.026* | |
| C4 | 0.10477 (14) | 0.4691 (4) | 0.3076 (6) | 0.0229 (7) | |
| H4 | 0.0995 | 0.4224 | 0.4569 | 0.027* | |
| C5 | 0.15882 (14) | 0.5176 (4) | 0.2671 (6) | 0.0237 (7) | |
| H5 | 0.1668 | 0.5538 | 0.1164 | 0.028* | |
| C6 | 0.20686 (15) | 0.5159 (4) | 0.4554 (6) | 0.0246 (7) | |
| C7 | 0.26819 (14) | 0.5103 (4) | 0.3861 (6) | 0.0217 (7) | |
| C8 | 0.28095 (14) | 0.4390 (4) | 0.1750 (6) | 0.0241 (7) | |
| H8 | 0.2501 | 0.4002 | 0.0659 | 0.029* | |
| C9 | 0.33836 (15) | 0.4239 (5) | 0.1218 (6) | 0.0264 (7) | |
| H9 | 0.3471 | 0.3707 | −0.0205 | 0.032* | |
| C10 | 0.38278 (14) | 0.4877 (5) | 0.2800 (6) | 0.0249 (7) | |
| C11 | 0.37131 (15) | 0.5624 (5) | 0.4894 (6) | 0.0282 (8) | |
| H11 | 0.4023 | 0.6067 | 0.5947 | 0.034* | |
| C12 | 0.31431 (15) | 0.5719 (4) | 0.5438 (6) | 0.0256 (7) | |
| H12 | 0.3060 | 0.6205 | 0.6891 | 0.031* | |
| O1 | 0.19730 (10) | 0.5193 (4) | 0.6579 (4) | 0.0313 (6) | |
| Cl1 | 0.45434 (4) | 0.47454 (16) | 0.20782 (17) | 0.0420 (4) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0257 (15) | 0.0183 (14) | 0.0209 (15) | −0.0002 (12) | 0.0004 (12) | −0.0028 (12) |
| C2 | 0.0198 (14) | 0.0192 (14) | 0.0208 (15) | 0.0006 (11) | 0.0013 (11) | −0.0028 (12) |
| C3 | 0.0188 (14) | 0.0203 (14) | 0.0270 (16) | −0.0026 (11) | 0.0024 (12) | −0.0008 (12) |
| C4 | 0.0239 (16) | 0.0223 (15) | 0.0215 (16) | 0.0013 (12) | −0.0025 (13) | −0.0004 (12) |
| C5 | 0.0237 (16) | 0.0262 (16) | 0.0207 (16) | 0.0030 (12) | −0.0012 (12) | 0.0022 (13) |
| C6 | 0.0254 (16) | 0.0203 (15) | 0.0272 (18) | 0.0025 (12) | −0.0034 (13) | −0.0014 (13) |
| C7 | 0.0215 (15) | 0.0190 (14) | 0.0235 (16) | 0.0025 (12) | −0.0044 (12) | 0.0021 (12) |
| C8 | 0.0244 (16) | 0.0216 (15) | 0.0250 (17) | 0.0006 (12) | −0.0047 (13) | −0.0020 (13) |
| C9 | 0.0280 (17) | 0.0244 (16) | 0.0266 (17) | 0.0039 (13) | 0.0017 (13) | −0.0002 (13) |
| C10 | 0.0213 (15) | 0.0271 (16) | 0.0268 (17) | 0.0005 (13) | 0.0045 (13) | 0.0034 (13) |
| C11 | 0.0261 (17) | 0.0267 (17) | 0.0302 (18) | 0.0003 (13) | −0.0062 (14) | 0.0018 (14) |
| C12 | 0.0312 (17) | 0.0197 (15) | 0.0245 (16) | 0.0007 (12) | −0.0059 (14) | −0.0008 (13) |
| O1 | 0.0244 (12) | 0.0489 (16) | 0.0209 (13) | 0.0015 (10) | 0.0031 (9) | 0.0000 (10) |
| Cl1 | 0.0227 (5) | 0.0617 (7) | 0.0423 (6) | 0.0030 (4) | 0.0066 (4) | 0.0023 (4) |
| C1—C3i | 1.388 (4) | C6—C7 | 1.502 (5) |
| C1—C2 | 1.401 (5) | C7—C8 | 1.387 (5) |
| C1—H1 | 0.950 | C7—C12 | 1.408 (4) |
| C2—C3 | 1.390 (5) | C8—C9 | 1.387 (5) |
| C2—C4 | 1.471 (4) | C8—H8 | 0.950 |
| C3—C1i | 1.388 (4) | C9—C10 | 1.388 (5) |
| C3—H3 | 0.950 | C9—H9 | 0.950 |
| C4—C5 | 1.330 (5) | C10—C11 | 1.379 (5) |
| C4—H4 | 0.950 | C10—Cl1 | 1.737 (3) |
| C5—C6 | 1.486 (4) | C11—C12 | 1.377 (5) |
| C5—H5 | 0.950 | C11—H11 | 0.950 |
| C6—O1 | 1.223 (4) | C12—H12 | 0.950 |
| C3i—C1—C2 | 121.3 (3) | C8—C7—C12 | 119.1 (3) |
| C3i—C1—H1 | 119.4 | C8—C7—C6 | 121.9 (3) |
| C2—C1—H1 | 119.4 | C12—C7—C6 | 119.0 (3) |
| C3—C2—C1 | 118.3 (3) | C9—C8—C7 | 120.6 (3) |
| C3—C2—C4 | 123.1 (3) | C9—C8—H8 | 119.7 |
| C1—C2—C4 | 118.5 (3) | C7—C8—H8 | 119.7 |
| C1i—C3—C2 | 120.4 (3) | C8—C9—C10 | 118.8 (3) |
| C1i—C3—H3 | 119.8 | C8—C9—H9 | 120.6 |
| C2—C3—H3 | 119.8 | C10—C9—H9 | 120.6 |
| C5—C4—C2 | 126.3 (3) | C11—C10—C9 | 121.7 (3) |
| C5—C4—H4 | 116.9 | C11—C10—Cl1 | 119.8 (3) |
| C2—C4—H4 | 116.9 | C9—C10—Cl1 | 118.4 (3) |
| C4—C5—C6 | 120.6 (3) | C12—C11—C10 | 119.1 (3) |
| C4—C5—H5 | 119.7 | C12—C11—H11 | 120.5 |
| C6—C5—H5 | 119.7 | C10—C11—H11 | 120.5 |
| O1—C6—C5 | 121.9 (3) | C11—C12—C7 | 120.6 (3) |
| O1—C6—C7 | 121.1 (3) | C11—C12—H12 | 119.7 |
| C5—C6—C7 | 116.9 (3) | C7—C12—H12 | 119.7 |
| C3i—C1—C2—C3 | −1.6 (5) | C5—C6—C7—C12 | 158.7 (3) |
| C3i—C1—C2—C4 | 175.0 (3) | C12—C7—C8—C9 | 1.6 (5) |
| C1—C2—C3—C1i | 1.6 (5) | C6—C7—C8—C9 | −175.7 (3) |
| C4—C2—C3—C1i | −174.8 (3) | C7—C8—C9—C10 | −2.3 (5) |
| C3—C2—C4—C5 | −4.1 (5) | C8—C9—C10—C11 | 1.2 (5) |
| C1—C2—C4—C5 | 179.5 (3) | C8—C9—C10—Cl1 | −178.1 (2) |
| C2—C4—C5—C6 | 174.1 (3) | C9—C10—C11—C12 | 0.7 (5) |
| C4—C5—C6—O1 | −19.3 (5) | Cl1—C10—C11—C12 | 180.0 (2) |
| C4—C5—C6—C7 | 160.9 (3) | C10—C11—C12—C7 | −1.4 (5) |
| O1—C6—C7—C8 | 156.2 (3) | C8—C7—C12—C11 | 0.3 (5) |
| C5—C6—C7—C8 | −24.0 (4) | C6—C7—C12—C11 | 177.6 (3) |
| O1—C6—C7—C12 | −21.1 (4) |
| Symmetry codes: (i) −x, −y+1, −z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C1—H1···Cg1ii | 0.95 | 2.70 | 3.400 (3) | 131 |
| C9—H9···Cg2iii | 0.95 | 2.77 | 3.422 (4) | 127 |
| C12—H12···Cg2iv | 0.95 | 2.83 | 3.457 (3) | 124 |
| Symmetry codes: (ii) −x, y−1/2, −z+1/2; (iii) x, −y+1/2, z−1/2; (iv) x, −y+3/2, z+1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C1—H1···Cg1i | 0.95 | 2.70 | 3.400 (3) | 131 |
| C9—H9···Cg2ii | 0.95 | 2.77 | 3.422 (4) | 127 |
| C12—H12···Cg2iii | 0.95 | 2.83 | 3.457 (3) | 124 |
| Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x, −y+1/2, z−1/2; (iii) x, −y+3/2, z+1/2. |
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As part of our ongoing studies of organic nonlinear optical materials derived from substituted chalcones (Harrison et al., 2007a,b), we report here the synthesis and structure of the title compound (Fig. 1).
The molecule is centrosymmetric and the dihedral angle between the mean planes of the central C1–C3/C1i–C3i [symmetry code: (i) −x, 1 − y, −z] and pendant C7–C12 benzene rings is 46.27 (9)°. The linking enone (C4/C5/C6/O1) fragment is substantially twisted, with a torsion angle of −19.3 (5)°.
In the crystal, the molecules lie in sheets in the (100) planes, with C—H···π interactions observed between molecules (Table 1, Figs. 2 and 3). Inter-sheet Cl1···Cl1ii contacts [symmetry code: (ii) 1 − x, 1 − y, −z] of 3.3701 (14)Å are formed, which are slightly short compared to the expected van der Waals separation of 3.50 Å.