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In the title cocrystal, 1-(4-chloro­phen­yl)-3-(3,4,5-trimethoxy­phen­yl)prop-2-en-1-one–3-(3-chloro-4,5-dimethoxy­phen­yl)-1-(4-chloro­phen­yl)prop-2-en-1-one (19/1), 0.95C18H17ClO4·0.05C17H14Cl2O3, the crystal packing is stabilized by weak inter­molecular C—H...O and π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806020769/sj2089sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806020769/sj2089Isup2.hkl
Contains datablock I

CCDC reference: 613825

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.001 Å
  • Disorder in main residue
  • R factor = 0.043
  • wR factor = 0.117
  • Data-to-parameter ratio = 34.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms .. ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.06 PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 22.09 Deg. O2 -C12 -CL2 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: H.K. Fun and I.A. Razak are supervisors of Shea-Lin Ng whereas S. M. Dharmaprakash is supervisor of Venkataraya Shettigar and P. S. Patil in this collaborative pulication. Mangalore University is involved in the extraction and synthesis of the title compound and USM is involved in the structure determination. All parties are involved in writing up the manuscript.

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

1-(4-chlorophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one–3-(3-chloro- 4,5-dimethoxyphenyl)-1-(4-chlorophenyl)-prop-2-en-1-one (19/1) top
Crystal data top
0.95C18H17ClO4·0.05C17H14Cl2O3F(000) = 696
Mr = 332.99Dx = 1.403 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5383 reflections
a = 7.5517 (1) Åθ = 2.0–37.5°
b = 15.9894 (2) ŵ = 0.27 mm1
c = 13.6914 (2) ÅT = 100 K
β = 107.491 (1)°Block, yellow
V = 1576.76 (4) Å30.48 × 0.29 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
8205 independent reflections
Radiation source: fine-focus sealed tube6659 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
Detector resolution: 8.33 pixels mm-1θmax = 37.5°, θmin = 2.0°
ω scansh = 1112
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 2527
Tmin = 0.829, Tmax = 0.949l = 2323
54905 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118Only H-atom coordinates refined
S = 1.03 w = 1/[σ2(Fo2) + (0.0593P)2 + 0.3778P]
where P = (Fo2 + 2Fc2)/3
8205 reflections(Δ/σ)max = 0.001
235 parametersΔρmax = 0.60 e Å3
0 restraintsΔρmin = 0.29 e Å3
Special details top

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) top
xyzUiso*/UeqOcc. (<1)
Cl10.26314 (3)0.036431 (15)0.048792 (16)0.02339 (6)
O10.09304 (10)0.03333 (4)0.40221 (5)0.01918 (12)
O20.42928 (11)0.23592 (5)0.86696 (5)0.01879 (12)0.95
C160.2614 (2)0.20325 (7)0.88009 (8)0.02203 (19)0.95
H16A0.25080.22080.94520.032 (4)*0.95
H16B0.26350.14330.87740.027 (4)*0.95
H16C0.15710.22390.82640.026 (4)*0.95
Cl20.3488 (11)0.2094 (3)0.8835 (3)0.0260 (10)0.05
O30.73553 (11)0.29782 (5)0.84878 (5)0.02495 (15)
O40.84485 (10)0.27023 (4)0.67746 (5)0.01971 (12)
C10.29291 (13)0.06698 (5)0.22211 (6)0.01851 (14)
H1A0.33750.11600.25760.025 (3)*
C20.30698 (14)0.05539 (6)0.12358 (6)0.02035 (15)
H2A0.35980.09640.09290.028 (4)*
C30.24059 (12)0.01858 (6)0.07217 (6)0.01790 (14)
C40.15617 (13)0.07945 (6)0.11535 (6)0.01840 (14)
H4A0.11030.12810.07950.022 (3)*
C50.14144 (12)0.06654 (5)0.21276 (6)0.01632 (13)
H5A0.08340.10660.24180.019 (3)*
C60.21247 (11)0.00568 (5)0.26783 (6)0.01458 (13)
C70.19937 (11)0.01283 (5)0.37470 (6)0.01455 (13)
C80.31886 (12)0.07429 (5)0.44439 (6)0.01608 (13)
H8A0.41280.10090.42530.023 (3)*
C90.29390 (12)0.09235 (5)0.53548 (6)0.01496 (13)
H9A0.19530.06630.55070.023 (3)*
C100.40825 (11)0.14941 (5)0.61257 (6)0.01464 (13)
C110.35781 (12)0.16382 (5)0.70188 (6)0.01575 (13)
H11A0.25290.13820.71050.023 (3)*
C120.46580 (12)0.21671 (5)0.77773 (6)0.01609 (13)
C130.62649 (12)0.25415 (5)0.76673 (6)0.01686 (14)
C140.67837 (12)0.23762 (5)0.67819 (6)0.01580 (13)
C150.56747 (12)0.18736 (5)0.60067 (6)0.01570 (13)
H15A0.59920.17900.54080.025 (3)*
C170.79406 (15)0.38026 (6)0.83215 (7)0.02447 (18)
H17A0.84120.40850.89670.032 (4)*
H17B0.69050.41090.78920.050 (5)*
H17C0.88990.37680.79950.045 (5)*
C180.90061 (14)0.25371 (6)0.58809 (7)0.02052 (15)
H18A1.01460.28260.59340.032 (4)*
H18B0.80580.27280.52840.018 (3)*
H18C0.91870.19470.58260.029 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.02906 (12)0.02670 (11)0.01587 (8)0.00048 (8)0.00896 (7)0.00372 (7)
O10.0227 (3)0.0168 (3)0.0208 (3)0.0044 (2)0.0107 (2)0.0029 (2)
O20.0223 (3)0.0215 (3)0.0138 (2)0.0066 (2)0.0073 (2)0.0057 (2)
C160.0269 (6)0.0240 (5)0.0178 (4)0.0070 (4)0.0107 (4)0.0048 (3)
Cl20.041 (3)0.023 (2)0.0144 (16)0.001 (2)0.010 (2)0.0053 (14)
O30.0338 (4)0.0241 (3)0.0133 (2)0.0126 (3)0.0016 (2)0.0022 (2)
O40.0191 (3)0.0239 (3)0.0156 (2)0.0061 (2)0.0044 (2)0.0005 (2)
C10.0242 (4)0.0155 (3)0.0169 (3)0.0039 (3)0.0077 (3)0.0025 (3)
C20.0270 (4)0.0193 (4)0.0164 (3)0.0035 (3)0.0090 (3)0.0011 (3)
C30.0192 (4)0.0198 (4)0.0146 (3)0.0015 (3)0.0050 (3)0.0022 (3)
C40.0213 (4)0.0168 (3)0.0167 (3)0.0009 (3)0.0050 (3)0.0041 (3)
C50.0181 (4)0.0147 (3)0.0158 (3)0.0016 (2)0.0046 (2)0.0021 (2)
C60.0160 (3)0.0137 (3)0.0142 (3)0.0001 (2)0.0048 (2)0.0019 (2)
C70.0160 (3)0.0131 (3)0.0148 (3)0.0005 (2)0.0050 (2)0.0016 (2)
C80.0169 (3)0.0167 (3)0.0148 (3)0.0022 (2)0.0052 (2)0.0018 (2)
C90.0155 (3)0.0150 (3)0.0140 (3)0.0007 (2)0.0039 (2)0.0011 (2)
C100.0155 (3)0.0149 (3)0.0125 (3)0.0000 (2)0.0028 (2)0.0006 (2)
C110.0170 (3)0.0160 (3)0.0140 (3)0.0012 (2)0.0043 (2)0.0014 (2)
C120.0204 (4)0.0152 (3)0.0123 (3)0.0007 (2)0.0043 (2)0.0008 (2)
C130.0206 (4)0.0158 (3)0.0122 (3)0.0029 (3)0.0018 (2)0.0002 (2)
C140.0167 (3)0.0161 (3)0.0134 (3)0.0022 (2)0.0027 (2)0.0013 (2)
C150.0168 (3)0.0168 (3)0.0126 (3)0.0014 (2)0.0030 (2)0.0002 (2)
C170.0274 (5)0.0209 (4)0.0239 (4)0.0083 (3)0.0059 (3)0.0049 (3)
C180.0217 (4)0.0221 (4)0.0189 (3)0.0040 (3)0.0079 (3)0.0008 (3)
Geometric parameters (Å, º) top
Cl1—C31.7386 (8)C5—C61.3952 (11)
O1—C71.2301 (10)C5—H5A0.9301
O2—C121.3659 (10)C6—C71.5002 (11)
O2—C161.4318 (15)C7—C81.4740 (11)
C16—H16A0.9601C8—C91.3474 (11)
C16—H16B0.9599C8—H8A0.9299
C16—H16C0.9600C9—C101.4644 (11)
Cl2—C121.913 (6)C9—H9A0.9299
Cl2—H16A1.2921C10—C151.3994 (12)
Cl2—H16B1.2276C10—C111.4048 (11)
Cl2—H16C1.4426C11—C121.3963 (11)
O3—C131.3682 (10)C11—H11A0.9301
O3—C171.4301 (12)C12—C131.4012 (12)
O4—C141.3638 (11)C13—C141.4064 (12)
O4—C181.4332 (11)C14—C151.3926 (11)
C1—C61.3965 (12)C15—H15A0.9300
C1—C21.3970 (12)C17—H17A0.9600
C1—H1A0.9301C17—H17B0.9600
C2—C31.3906 (13)C17—H17C0.9601
C2—H2A0.9300C18—H18A0.9600
C3—C41.3892 (13)C18—H18B0.9600
C4—C51.3867 (11)C18—H18C0.9601
C4—H4A0.9300
C12—O2—C16117.05 (7)C7—C8—H8A119.6
O2—C16—H16A109.5C8—C9—C10125.77 (8)
O2—C16—H16B109.5C8—C9—H9A117.1
H16A—C16—H16B109.5C10—C9—H9A117.1
O2—C16—H16C109.4C15—C10—C11119.84 (7)
H16A—C16—H16C109.5C15—C10—C9121.83 (7)
H16B—C16—H16C109.5C11—C10—C9118.30 (7)
C12—Cl2—H16A166.3C12—C11—C10119.74 (8)
C12—Cl2—H16B110.7C12—C11—H11A120.1
H16A—Cl2—H16B76.9C10—C11—H11A120.1
C12—Cl2—H16C101.3O2—C12—C11124.87 (8)
H16A—Cl2—H16C69.7O2—C12—C13114.47 (7)
H16B—Cl2—H16C71.4C11—C12—C13120.66 (7)
C13—O3—C17118.57 (7)O2—C12—Cl222.09 (18)
C14—O4—C18116.34 (7)C11—C12—Cl2103.1 (2)
C6—C1—C2120.62 (8)C13—C12—Cl2136.0 (2)
C6—C1—H1A119.7O3—C13—C12117.18 (7)
C2—C1—H1A119.7O3—C13—C14123.28 (8)
C3—C2—C1118.76 (8)C12—C13—C14119.14 (7)
C3—C2—H2A120.6O4—C14—C15124.02 (7)
C1—C2—H2A120.6O4—C14—C13115.51 (7)
C4—C3—C2121.49 (8)C15—C14—C13120.38 (8)
C4—C3—Cl1118.64 (6)C14—C15—C10120.16 (7)
C2—C3—Cl1119.87 (7)C14—C15—H15A119.9
C5—C4—C3118.99 (8)C10—C15—H15A119.9
C5—C4—H4A120.5O3—C17—H17A109.5
C3—C4—H4A120.5O3—C17—H17B109.5
C4—C5—C6120.94 (8)H17A—C17—H17B109.5
C4—C5—H5A119.5O3—C17—H17C109.4
C6—C5—H5A119.5H17A—C17—H17C109.5
C5—C6—C1119.14 (7)H17B—C17—H17C109.5
C5—C6—C7117.57 (7)O4—C18—H18A109.5
C1—C6—C7123.28 (7)O4—C18—H18B109.5
O1—C7—C8122.06 (7)H18A—C18—H18B109.5
O1—C7—C6119.56 (7)O4—C18—H18C109.5
C8—C7—C6118.37 (7)H18A—C18—H18C109.5
C9—C8—C7120.89 (8)H18B—C18—H18C109.5
C9—C8—H8A119.6
C6—C1—C2—C30.46 (14)C16—O2—C12—Cl214.8 (5)
C1—C2—C3—C42.00 (14)C10—C11—C12—O2179.31 (8)
C1—C2—C3—Cl1177.83 (7)C10—C11—C12—C131.44 (13)
C2—C3—C4—C51.29 (14)C10—C11—C12—Cl2176.56 (19)
Cl1—C3—C4—C5178.54 (7)C17—O3—C13—C12130.90 (9)
C3—C4—C5—C60.99 (13)C17—O3—C13—C1456.42 (13)
C4—C5—C6—C12.49 (13)O2—C12—C13—O36.16 (12)
C4—C5—C6—C7176.99 (8)C11—C12—C13—O3173.17 (8)
C2—C1—C6—C51.74 (14)Cl2—C12—C13—O30.0 (3)
C2—C1—C6—C7177.70 (8)O2—C12—C13—C14179.15 (8)
C5—C6—C7—O116.38 (12)C11—C12—C13—C140.18 (13)
C1—C6—C7—O1164.17 (9)Cl2—C12—C13—C14173.0 (3)
C5—C6—C7—C8162.24 (8)C18—O4—C14—C153.00 (12)
C1—C6—C7—C817.21 (12)C18—O4—C14—C13179.69 (8)
O1—C7—C8—C911.41 (13)O3—C13—C14—O41.76 (12)
C6—C7—C8—C9170.02 (8)C12—C13—C14—O4174.30 (8)
C7—C8—C9—C10177.30 (8)O3—C13—C14—C15175.07 (8)
C8—C9—C10—C154.57 (13)C12—C13—C14—C152.53 (12)
C8—C9—C10—C11177.35 (8)O4—C14—C15—C10173.29 (8)
C15—C10—C11—C120.73 (12)C13—C14—C15—C103.25 (13)
C9—C10—C11—C12178.86 (7)C11—C10—C15—C141.60 (12)
C16—O2—C12—C114.07 (13)C9—C10—C15—C14176.45 (8)
C16—O2—C12—C13176.64 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O10.932.512.829 (1)100
C17—H17C···O40.962.342.866 (1)114
C9—H9A···O1i0.932.513.414 (1)166
C18—H18C···O1ii0.962.593.526 (1)164
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z+1.
 

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