organic compounds
3-(4-Chlorobenzoyl)-6-(4-chlorophenyl)-2,4-dimethylbenzonitrile
aSchool of Chemistry and Environmental Science, Henan Normal University, Xinxiang, Henan 453007, People's Republic of China, and bXinyang Agricultural College, Xinyang, Henan 464000, People's Republic of China
*Correspondence e-mail: hxxzhym@sina.com
In the title compound, C22H15Cl2NO, the terminal chlorobenzene rings are oriented at 44.51 (15) and 86.06 (17)° with respect to the central polysubstituted benzene ring, and make a dihedral angle of 49.48 (17)°with each other. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯N interactions.
Related literature
For background to the title compound, see: Ma (2003, 2005, 2007); Hoffmann-Röder et al. (2004). For related structures, see: Zhang et al. (2011); Fun et al. (2012); Jagadeesan et al. (2011).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536812036409/xu5613sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812036409/xu5613Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812036409/xu5613Isup3.cdx
Supporting information file. DOI: 10.1107/S1600536812036409/xu5613Isup4.cml
A mixture of 1-(4-chlorophenyl)buta-2,3-dien-1-one (1 mmol), cyanoacetate (0.5 mmol) and K2CO3 (0.5 mmol) in acetone (5 ml) was refluxed for 15 min. Upon completion, the reaction mixture was cooled to room temperature, added with water (10 ml) and extracted with ethyl acetate. The combined organic phases were washed with brine, dried, filtered and concentrated under vacuum. The residue was purified by
on silica gel eluting with ethyl acetate/hexane (1:20 v/v) to give the title compound as Colorless solids with a yield of 80%. Single crystals, suitable for X-ray were obtained by slow evaporation of solvent from a petroleum ether-dichloromethane (2:1 v/v) solution.The H atoms were included at calculated positions and were refined as riding atoms: C—H = 0.93 and 0.96 Å for aromatic and methyl H atoms, respectively, with Uiso(H) =xUeq(C), where x = 1.2 for aromatic H, and x = 1.5 for methyl H atoms.
Data collection: SMART (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. Molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. Fig. 2. of the title compound, viewed along the a axis. Intermolecular C—H···O and C—H···N hydrogen bonds are shown as dashed lines, only H atoms involved in hydrogen bonds are shown. |
C22H15Cl2NO | F(000) = 784 |
Mr = 380.25 | Dx = 1.351 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3123 reflections |
a = 7.8102 (12) Å | θ = 2.6–22.9° |
b = 30.032 (5) Å | µ = 0.36 mm−1 |
c = 8.2054 (13) Å | T = 296 K |
β = 103.739 (2)° | Block, colourless |
V = 1869.6 (5) Å3 | 0.39 × 0.33 × 0.23 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 3442 independent reflections |
Radiation source: fine-focus sealed tube | 2013 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
phi and ω scans | θmax = 25.5°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −9→9 |
Tmin = 0.873, Tmax = 0.922 | k = −36→36 |
11684 measured reflections | l = −9→9 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0235P)2 + 1.9216P] where P = (Fo2 + 2Fc2)/3 |
3442 reflections | (Δ/σ)max < 0.001 |
237 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C22H15Cl2NO | V = 1869.6 (5) Å3 |
Mr = 380.25 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.8102 (12) Å | µ = 0.36 mm−1 |
b = 30.032 (5) Å | T = 296 K |
c = 8.2054 (13) Å | 0.39 × 0.33 × 0.23 mm |
β = 103.739 (2)° |
Bruker SMART CCD area-detector diffractometer | 3442 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 2013 reflections with I > 2σ(I) |
Tmin = 0.873, Tmax = 0.922 | Rint = 0.034 |
11684 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.21 e Å−3 |
3442 reflections | Δρmin = −0.24 e Å−3 |
237 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.7995 (4) | 0.21705 (10) | 0.1502 (4) | 0.0402 (7) | |
C2 | 0.6497 (4) | 0.20687 (10) | 0.2063 (4) | 0.0452 (8) | |
H2 | 0.5945 | 0.2292 | 0.2535 | 0.054* | |
C3 | 0.5808 (4) | 0.16426 (11) | 0.1934 (4) | 0.0525 (9) | |
H3 | 0.4806 | 0.1580 | 0.2318 | 0.063* | |
C4 | 0.6621 (5) | 0.13136 (10) | 0.1233 (4) | 0.0518 (9) | |
C5 | 0.8084 (5) | 0.14040 (11) | 0.0632 (4) | 0.0529 (9) | |
H5 | 0.8606 | 0.1181 | 0.0131 | 0.063* | |
C6 | 0.8767 (4) | 0.18288 (10) | 0.0779 (4) | 0.0483 (8) | |
H6 | 0.9767 | 0.1889 | 0.0386 | 0.058* | |
C7 | 0.8714 (4) | 0.26288 (10) | 0.1663 (4) | 0.0398 (7) | |
C8 | 1.0517 (4) | 0.27148 (10) | 0.2239 (4) | 0.0442 (8) | |
C9 | 1.1199 (4) | 0.31495 (11) | 0.2343 (4) | 0.0483 (8) | |
C10 | 1.0020 (4) | 0.35035 (10) | 0.1930 (4) | 0.0460 (8) | |
C11 | 0.8210 (4) | 0.34288 (10) | 0.1389 (4) | 0.0467 (8) | |
C12 | 0.7596 (4) | 0.29920 (10) | 0.1238 (4) | 0.0451 (8) | |
H12 | 0.6394 | 0.2942 | 0.0838 | 0.054* | |
C13 | 1.1720 (5) | 0.23601 (12) | 0.2910 (5) | 0.0558 (9) | |
C14 | 1.3152 (5) | 0.32286 (14) | 0.2910 (5) | 0.0772 (12) | |
H14A | 1.3698 | 0.3164 | 0.2005 | 0.116* | |
H14B | 1.3639 | 0.3038 | 0.3845 | 0.116* | |
H14C | 1.3365 | 0.3534 | 0.3241 | 0.116* | |
C15 | 0.6925 (5) | 0.38100 (11) | 0.0981 (5) | 0.0646 (10) | |
H15A | 0.5752 | 0.3695 | 0.0592 | 0.097* | |
H15B | 0.7215 | 0.3991 | 0.0122 | 0.097* | |
H15C | 0.6988 | 0.3986 | 0.1969 | 0.097* | |
C16 | 1.0722 (5) | 0.39731 (11) | 0.2256 (5) | 0.0547 (9) | |
C17 | 1.1277 (4) | 0.42252 (11) | 0.0920 (4) | 0.0495 (8) | |
C18 | 1.2013 (5) | 0.46432 (11) | 0.1290 (5) | 0.0634 (10) | |
H18 | 1.2167 | 0.4758 | 0.2367 | 0.076* | |
C19 | 1.2517 (5) | 0.48886 (12) | 0.0070 (5) | 0.0693 (11) | |
H19 | 1.3029 | 0.5167 | 0.0326 | 0.083* | |
C20 | 1.2263 (5) | 0.47210 (11) | −0.1532 (5) | 0.0589 (10) | |
C21 | 1.1562 (5) | 0.43075 (11) | −0.1909 (5) | 0.0658 (11) | |
H21 | 1.1412 | 0.4194 | −0.2988 | 0.079* | |
C22 | 1.1076 (5) | 0.40580 (11) | −0.0673 (5) | 0.0619 (10) | |
H22 | 1.0608 | 0.3774 | −0.0924 | 0.074* | |
Cl1 | 0.57545 (16) | 0.07788 (3) | 0.10760 (15) | 0.0838 (4) | |
Cl2 | 1.28408 (16) | 0.50406 (3) | −0.30697 (14) | 0.0848 (4) | |
N1 | 1.2698 (4) | 0.20909 (12) | 0.3525 (5) | 0.0805 (11) | |
O1 | 1.0819 (4) | 0.41318 (9) | 0.3638 (3) | 0.0857 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0442 (18) | 0.0436 (17) | 0.0329 (18) | 0.0008 (14) | 0.0092 (14) | 0.0012 (14) |
C2 | 0.049 (2) | 0.0429 (18) | 0.045 (2) | 0.0041 (15) | 0.0140 (16) | −0.0021 (15) |
C3 | 0.055 (2) | 0.051 (2) | 0.054 (2) | −0.0044 (17) | 0.0172 (17) | 0.0015 (17) |
C4 | 0.067 (2) | 0.0420 (18) | 0.045 (2) | −0.0002 (17) | 0.0117 (18) | 0.0021 (16) |
C5 | 0.069 (2) | 0.050 (2) | 0.041 (2) | 0.0109 (18) | 0.0164 (18) | −0.0040 (16) |
C6 | 0.057 (2) | 0.0477 (19) | 0.044 (2) | 0.0038 (17) | 0.0204 (17) | 0.0003 (16) |
C7 | 0.0453 (19) | 0.0439 (18) | 0.0323 (18) | −0.0010 (15) | 0.0130 (15) | −0.0001 (14) |
C8 | 0.045 (2) | 0.0508 (19) | 0.040 (2) | 0.0009 (16) | 0.0165 (15) | −0.0008 (15) |
C9 | 0.046 (2) | 0.061 (2) | 0.039 (2) | −0.0086 (17) | 0.0138 (16) | −0.0054 (16) |
C10 | 0.057 (2) | 0.0502 (19) | 0.0314 (19) | −0.0099 (17) | 0.0125 (16) | −0.0035 (14) |
C11 | 0.058 (2) | 0.0470 (19) | 0.0354 (19) | −0.0021 (16) | 0.0117 (16) | 0.0022 (15) |
C12 | 0.0446 (19) | 0.0485 (19) | 0.042 (2) | −0.0017 (16) | 0.0095 (15) | 0.0012 (15) |
C13 | 0.050 (2) | 0.062 (2) | 0.059 (2) | 0.0008 (19) | 0.0207 (19) | 0.0016 (19) |
C14 | 0.054 (2) | 0.085 (3) | 0.090 (3) | −0.016 (2) | 0.013 (2) | −0.010 (2) |
C15 | 0.070 (3) | 0.044 (2) | 0.076 (3) | 0.0014 (18) | 0.011 (2) | 0.0032 (18) |
C16 | 0.063 (2) | 0.055 (2) | 0.048 (2) | −0.0154 (18) | 0.0178 (18) | −0.0095 (18) |
C17 | 0.059 (2) | 0.0467 (18) | 0.044 (2) | −0.0116 (17) | 0.0144 (17) | −0.0070 (16) |
C18 | 0.083 (3) | 0.053 (2) | 0.057 (2) | −0.023 (2) | 0.021 (2) | −0.0158 (18) |
C19 | 0.092 (3) | 0.043 (2) | 0.077 (3) | −0.022 (2) | 0.030 (2) | −0.010 (2) |
C20 | 0.070 (3) | 0.045 (2) | 0.066 (3) | −0.0041 (18) | 0.026 (2) | 0.0057 (18) |
C21 | 0.094 (3) | 0.053 (2) | 0.056 (2) | −0.020 (2) | 0.028 (2) | −0.0097 (18) |
C22 | 0.082 (3) | 0.049 (2) | 0.058 (3) | −0.0240 (19) | 0.022 (2) | −0.0079 (18) |
Cl1 | 0.1082 (9) | 0.0465 (5) | 0.1010 (9) | −0.0146 (5) | 0.0337 (7) | −0.0085 (5) |
Cl2 | 0.1219 (10) | 0.0556 (6) | 0.0896 (8) | −0.0063 (6) | 0.0505 (7) | 0.0130 (5) |
N1 | 0.065 (2) | 0.083 (2) | 0.095 (3) | 0.018 (2) | 0.023 (2) | 0.014 (2) |
O1 | 0.127 (3) | 0.0814 (19) | 0.0601 (19) | −0.0443 (17) | 0.0442 (18) | −0.0276 (15) |
C1—C2 | 1.389 (4) | C12—H12 | 0.9300 |
C1—C6 | 1.393 (4) | C13—N1 | 1.144 (4) |
C1—C7 | 1.481 (4) | C14—H14A | 0.9600 |
C2—C3 | 1.382 (4) | C14—H14B | 0.9600 |
C2—H2 | 0.9300 | C14—H14C | 0.9600 |
C3—C4 | 1.373 (4) | C15—H15A | 0.9600 |
C3—H3 | 0.9300 | C15—H15B | 0.9600 |
C4—C5 | 1.374 (5) | C15—H15C | 0.9600 |
C4—Cl1 | 1.736 (3) | C16—O1 | 1.216 (4) |
C5—C6 | 1.377 (4) | C16—C17 | 1.479 (4) |
C5—H5 | 0.9300 | C17—C22 | 1.374 (4) |
C6—H6 | 0.9300 | C17—C18 | 1.384 (4) |
C7—C12 | 1.389 (4) | C18—C19 | 1.373 (5) |
C7—C8 | 1.398 (4) | C18—H18 | 0.9300 |
C8—C9 | 1.405 (4) | C19—C20 | 1.377 (5) |
C8—C13 | 1.440 (5) | C19—H19 | 0.9300 |
C9—C10 | 1.395 (4) | C20—C21 | 1.363 (5) |
C9—C14 | 1.504 (5) | C20—Cl2 | 1.729 (3) |
C10—C11 | 1.396 (4) | C21—C22 | 1.384 (5) |
C10—C16 | 1.514 (4) | C21—H21 | 0.9300 |
C11—C12 | 1.392 (4) | C22—H22 | 0.9300 |
C11—C15 | 1.507 (4) | ||
C2—C1—C6 | 117.6 (3) | C11—C12—H12 | 118.8 |
C2—C1—C7 | 120.4 (3) | N1—C13—C8 | 176.2 (4) |
C6—C1—C7 | 122.0 (3) | C9—C14—H14A | 109.5 |
C3—C2—C1 | 121.4 (3) | C9—C14—H14B | 109.5 |
C3—C2—H2 | 119.3 | H14A—C14—H14B | 109.5 |
C1—C2—H2 | 119.3 | C9—C14—H14C | 109.5 |
C4—C3—C2 | 119.2 (3) | H14A—C14—H14C | 109.5 |
C4—C3—H3 | 120.4 | H14B—C14—H14C | 109.5 |
C2—C3—H3 | 120.4 | C11—C15—H15A | 109.5 |
C3—C4—C5 | 121.0 (3) | C11—C15—H15B | 109.5 |
C3—C4—Cl1 | 119.1 (3) | H15A—C15—H15B | 109.5 |
C5—C4—Cl1 | 119.9 (3) | C11—C15—H15C | 109.5 |
C4—C5—C6 | 119.3 (3) | H15A—C15—H15C | 109.5 |
C4—C5—H5 | 120.3 | H15B—C15—H15C | 109.5 |
C6—C5—H5 | 120.3 | O1—C16—C17 | 121.8 (3) |
C5—C6—C1 | 121.5 (3) | O1—C16—C10 | 118.0 (3) |
C5—C6—H6 | 119.3 | C17—C16—C10 | 120.2 (3) |
C1—C6—H6 | 119.3 | C22—C17—C18 | 119.2 (3) |
C12—C7—C8 | 117.5 (3) | C22—C17—C16 | 122.0 (3) |
C12—C7—C1 | 120.3 (3) | C18—C17—C16 | 118.8 (3) |
C8—C7—C1 | 122.2 (3) | C19—C18—C17 | 120.2 (3) |
C7—C8—C9 | 121.9 (3) | C19—C18—H18 | 119.9 |
C7—C8—C13 | 120.4 (3) | C17—C18—H18 | 119.9 |
C9—C8—C13 | 117.4 (3) | C18—C19—C20 | 119.9 (3) |
C10—C9—C8 | 118.4 (3) | C18—C19—H19 | 120.1 |
C10—C9—C14 | 121.1 (3) | C20—C19—H19 | 120.1 |
C8—C9—C14 | 120.5 (3) | C21—C20—C19 | 120.6 (3) |
C9—C10—C11 | 121.0 (3) | C21—C20—Cl2 | 120.0 (3) |
C9—C10—C16 | 118.5 (3) | C19—C20—Cl2 | 119.4 (3) |
C11—C10—C16 | 120.2 (3) | C20—C21—C22 | 119.5 (3) |
C12—C11—C10 | 118.8 (3) | C20—C21—H21 | 120.3 |
C12—C11—C15 | 119.9 (3) | C22—C21—H21 | 120.3 |
C10—C11—C15 | 121.3 (3) | C17—C22—C21 | 120.6 (3) |
C7—C12—C11 | 122.3 (3) | C17—C22—H22 | 119.7 |
C7—C12—H12 | 118.8 | C21—C22—H22 | 119.7 |
C6—C1—C2—C3 | 1.0 (5) | C16—C10—C11—C12 | −174.6 (3) |
C7—C1—C2—C3 | −179.6 (3) | C9—C10—C11—C15 | 178.5 (3) |
C1—C2—C3—C4 | −0.2 (5) | C16—C10—C11—C15 | 5.1 (5) |
C2—C3—C4—C5 | −1.2 (5) | C8—C7—C12—C11 | −0.9 (4) |
C2—C3—C4—Cl1 | 179.9 (3) | C1—C7—C12—C11 | 179.2 (3) |
C3—C4—C5—C6 | 1.8 (5) | C10—C11—C12—C7 | 2.4 (5) |
Cl1—C4—C5—C6 | −179.4 (3) | C15—C11—C12—C7 | −177.3 (3) |
C4—C5—C6—C1 | −0.9 (5) | C7—C8—C13—N1 | −119 (6) |
C2—C1—C6—C5 | −0.4 (5) | C9—C8—C13—N1 | 55 (6) |
C7—C1—C6—C5 | −179.9 (3) | C9—C10—C16—O1 | −86.8 (4) |
C2—C1—C7—C12 | −44.8 (4) | C11—C10—C16—O1 | 86.8 (4) |
C6—C1—C7—C12 | 134.6 (3) | C9—C10—C16—C17 | 92.8 (4) |
C2—C1—C7—C8 | 135.3 (3) | C11—C10—C16—C17 | −93.6 (4) |
C6—C1—C7—C8 | −45.3 (4) | O1—C16—C17—C22 | −176.1 (4) |
C12—C7—C8—C9 | −1.9 (4) | C10—C16—C17—C22 | 4.3 (5) |
C1—C7—C8—C9 | 178.1 (3) | O1—C16—C17—C18 | 3.5 (6) |
C12—C7—C8—C13 | 171.8 (3) | C10—C16—C17—C18 | −176.1 (3) |
C1—C7—C8—C13 | −8.3 (4) | C22—C17—C18—C19 | 0.7 (6) |
C7—C8—C9—C10 | 3.0 (5) | C16—C17—C18—C19 | −179.0 (4) |
C13—C8—C9—C10 | −170.8 (3) | C17—C18—C19—C20 | 1.0 (6) |
C7—C8—C9—C14 | −177.8 (3) | C18—C19—C20—C21 | −1.9 (6) |
C13—C8—C9—C14 | 8.4 (5) | C18—C19—C20—Cl2 | 178.0 (3) |
C8—C9—C10—C11 | −1.4 (4) | C19—C20—C21—C22 | 1.1 (6) |
C14—C9—C10—C11 | 179.4 (3) | Cl2—C20—C21—C22 | −178.9 (3) |
C8—C9—C10—C16 | 172.1 (3) | C18—C17—C22—C21 | −1.5 (6) |
C14—C9—C10—C16 | −7.1 (5) | C16—C17—C22—C21 | 178.1 (4) |
C9—C10—C11—C12 | −1.2 (5) | C20—C21—C22—C17 | 0.6 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···N1i | 0.93 | 2.61 | 3.305 (5) | 132 |
C5—H5···O1ii | 0.93 | 2.53 | 3.390 (5) | 155 |
Symmetry codes: (i) x−1, y, z; (ii) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C22H15Cl2NO |
Mr | 380.25 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 7.8102 (12), 30.032 (5), 8.2054 (13) |
β (°) | 103.739 (2) |
V (Å3) | 1869.6 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.36 |
Crystal size (mm) | 0.39 × 0.33 × 0.23 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2007) |
Tmin, Tmax | 0.873, 0.922 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11684, 3442, 2013 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.121, 1.08 |
No. of reflections | 3442 |
No. of parameters | 237 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.24 |
Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···N1i | 0.93 | 2.61 | 3.305 (5) | 132.0 |
C5—H5···O1ii | 0.93 | 2.53 | 3.390 (5) | 155.0 |
Symmetry codes: (i) x−1, y, z; (ii) x, −y+1/2, z−1/2. |
Acknowledgements
This work was supported by the National Natural Science Foundation of China (No. 21172057).
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It has been well documented that benzenoid compounds are ubiquitous structural units in a wide variety of naturally occurring compounds and a plethora of pharmaceuticals. On the other hand, allene derivatives are powerful synthetic intermediates toward a plethora of important organic compounds and frequent building blocks of natural products (Ma, 2003, 2005, 2007; Hoffmann-Röder et al., 2004). In this regard, Zhang et al. have developed a novel and efficient method for the preparation of polysubstituted benzenes by one-pot double Michael addition/intramolecular aldol reaction/ decarboxylation of 1,2-allenic ketones with cyanoacetate (Zhang et al., 2011). Herein, we would like to report the structure of one of the products obtained by this method.
In the title compound (Fig. 1), all the bond lengths and bond angles are within normal ranges. The central polysubstituted benzene ring (C7—C12) forms dihedral angles of 44.51 (15)° and 86.06 (17)° with the other two chloro-substituted phenyl rings (C1—C6) and (C17—C22), respectively. And the dihedral angle between the two chloro-substituted phenyl rings, (C1—C7) and (C7—C12), is 49.48 (17)°. The mean plane of the ketone group is almost co-planar with the neighboring chloro-substituted phenyl ring (C17-C22).
In the crystal structure, the molecules are connected via C—H···O and C—H···N interactions.