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), 0.95C
18H
17ClO
4·0.05C
17H
14Cl
2O
3, the crystal packing is stabilized by weak intermolecular C—H
O and π–π interactions.
Supporting information
CCDC reference: 613825
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (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
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
0.95C18H17ClO4·0.05C17H14Cl2O3 | F(000) = 696 |
Mr = 332.99 | Dx = 1.403 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5383 reflections |
a = 7.5517 (1) Å | θ = 2.0–37.5° |
b = 15.9894 (2) Å | µ = 0.27 mm−1 |
c = 13.6914 (2) Å | T = 100 K |
β = 107.491 (1)° | Block, yellow |
V = 1576.76 (4) Å3 | 0.48 × 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 tube | 6659 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
Detector resolution: 8.33 pixels mm-1 | θmax = 37.5°, θmin = 2.0° |
ω scans | h = −11→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −25→27 |
Tmin = 0.829, Tmax = 0.949 | l = −23→23 |
54905 measured reflections | |
Refinement top
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | Only 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 parameters | Δρmax = 0.60 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cl1 | 0.26314 (3) | −0.036431 (15) | −0.048792 (16) | 0.02339 (6) | |
O1 | 0.09304 (10) | −0.03333 (4) | 0.40221 (5) | 0.01918 (12) | |
O2 | 0.42928 (11) | 0.23592 (5) | 0.86696 (5) | 0.01879 (12) | 0.95 |
C16 | 0.2614 (2) | 0.20325 (7) | 0.88009 (8) | 0.02203 (19) | 0.95 |
H16A | 0.2508 | 0.2208 | 0.9452 | 0.032 (4)* | 0.95 |
H16B | 0.2635 | 0.1433 | 0.8774 | 0.027 (4)* | 0.95 |
H16C | 0.1571 | 0.2239 | 0.8264 | 0.026 (4)* | 0.95 |
Cl2 | 0.3488 (11) | 0.2094 (3) | 0.8835 (3) | 0.0260 (10) | 0.05 |
O3 | 0.73553 (11) | 0.29782 (5) | 0.84878 (5) | 0.02495 (15) | |
O4 | 0.84485 (10) | 0.27023 (4) | 0.67746 (5) | 0.01971 (12) | |
C1 | 0.29291 (13) | 0.06698 (5) | 0.22211 (6) | 0.01851 (14) | |
H1A | 0.3375 | 0.1160 | 0.2576 | 0.025 (3)* | |
C2 | 0.30698 (14) | 0.05539 (6) | 0.12358 (6) | 0.02035 (15) | |
H2A | 0.3598 | 0.0964 | 0.0929 | 0.028 (4)* | |
C3 | 0.24059 (12) | −0.01858 (6) | 0.07217 (6) | 0.01790 (14) | |
C4 | 0.15617 (13) | −0.07945 (6) | 0.11535 (6) | 0.01840 (14) | |
H4A | 0.1103 | −0.1281 | 0.0795 | 0.022 (3)* | |
C5 | 0.14144 (12) | −0.06654 (5) | 0.21276 (6) | 0.01632 (13) | |
H5A | 0.0834 | −0.1066 | 0.2418 | 0.019 (3)* | |
C6 | 0.21247 (11) | 0.00568 (5) | 0.26783 (6) | 0.01458 (13) | |
C7 | 0.19937 (11) | 0.01283 (5) | 0.37470 (6) | 0.01455 (13) | |
C8 | 0.31886 (12) | 0.07429 (5) | 0.44439 (6) | 0.01608 (13) | |
H8A | 0.4128 | 0.1009 | 0.4253 | 0.023 (3)* | |
C9 | 0.29390 (12) | 0.09235 (5) | 0.53548 (6) | 0.01496 (13) | |
H9A | 0.1953 | 0.0663 | 0.5507 | 0.023 (3)* | |
C10 | 0.40825 (11) | 0.14941 (5) | 0.61257 (6) | 0.01464 (13) | |
C11 | 0.35781 (12) | 0.16382 (5) | 0.70188 (6) | 0.01575 (13) | |
H11A | 0.2529 | 0.1382 | 0.7105 | 0.023 (3)* | |
C12 | 0.46580 (12) | 0.21671 (5) | 0.77773 (6) | 0.01609 (13) | |
C13 | 0.62649 (12) | 0.25415 (5) | 0.76673 (6) | 0.01686 (14) | |
C14 | 0.67837 (12) | 0.23762 (5) | 0.67819 (6) | 0.01580 (13) | |
C15 | 0.56747 (12) | 0.18736 (5) | 0.60067 (6) | 0.01570 (13) | |
H15A | 0.5992 | 0.1790 | 0.5408 | 0.025 (3)* | |
C17 | 0.79406 (15) | 0.38026 (6) | 0.83215 (7) | 0.02447 (18) | |
H17A | 0.8412 | 0.4085 | 0.8967 | 0.032 (4)* | |
H17B | 0.6905 | 0.4109 | 0.7892 | 0.050 (5)* | |
H17C | 0.8899 | 0.3768 | 0.7995 | 0.045 (5)* | |
C18 | 0.90061 (14) | 0.25371 (6) | 0.58809 (7) | 0.02052 (15) | |
H18A | 1.0146 | 0.2826 | 0.5934 | 0.032 (4)* | |
H18B | 0.8058 | 0.2728 | 0.5284 | 0.018 (3)* | |
H18C | 0.9187 | 0.1947 | 0.5826 | 0.029 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.02906 (12) | 0.02670 (11) | 0.01587 (8) | 0.00048 (8) | 0.00896 (7) | −0.00372 (7) |
O1 | 0.0227 (3) | 0.0168 (3) | 0.0208 (3) | −0.0044 (2) | 0.0107 (2) | −0.0029 (2) |
O2 | 0.0223 (3) | 0.0215 (3) | 0.0138 (2) | −0.0066 (2) | 0.0073 (2) | −0.0057 (2) |
C16 | 0.0269 (6) | 0.0240 (5) | 0.0178 (4) | −0.0070 (4) | 0.0107 (4) | −0.0048 (3) |
Cl2 | 0.041 (3) | 0.023 (2) | 0.0144 (16) | −0.001 (2) | 0.010 (2) | −0.0053 (14) |
O3 | 0.0338 (4) | 0.0241 (3) | 0.0133 (2) | −0.0126 (3) | 0.0016 (2) | −0.0022 (2) |
O4 | 0.0191 (3) | 0.0239 (3) | 0.0156 (2) | −0.0061 (2) | 0.0044 (2) | −0.0005 (2) |
C1 | 0.0242 (4) | 0.0155 (3) | 0.0169 (3) | −0.0039 (3) | 0.0077 (3) | −0.0025 (3) |
C2 | 0.0270 (4) | 0.0193 (4) | 0.0164 (3) | −0.0035 (3) | 0.0090 (3) | −0.0011 (3) |
C3 | 0.0192 (4) | 0.0198 (4) | 0.0146 (3) | 0.0015 (3) | 0.0050 (3) | −0.0022 (3) |
C4 | 0.0213 (4) | 0.0168 (3) | 0.0167 (3) | −0.0009 (3) | 0.0050 (3) | −0.0041 (3) |
C5 | 0.0181 (4) | 0.0147 (3) | 0.0158 (3) | −0.0016 (2) | 0.0046 (2) | −0.0021 (2) |
C6 | 0.0160 (3) | 0.0137 (3) | 0.0142 (3) | −0.0001 (2) | 0.0048 (2) | −0.0019 (2) |
C7 | 0.0160 (3) | 0.0131 (3) | 0.0148 (3) | 0.0005 (2) | 0.0050 (2) | −0.0016 (2) |
C8 | 0.0169 (3) | 0.0167 (3) | 0.0148 (3) | −0.0022 (2) | 0.0052 (2) | −0.0018 (2) |
C9 | 0.0155 (3) | 0.0150 (3) | 0.0140 (3) | −0.0007 (2) | 0.0039 (2) | −0.0011 (2) |
C10 | 0.0155 (3) | 0.0149 (3) | 0.0125 (3) | 0.0000 (2) | 0.0028 (2) | −0.0006 (2) |
C11 | 0.0170 (3) | 0.0160 (3) | 0.0140 (3) | −0.0012 (2) | 0.0043 (2) | −0.0014 (2) |
C12 | 0.0204 (4) | 0.0152 (3) | 0.0123 (3) | −0.0007 (2) | 0.0043 (2) | −0.0008 (2) |
C13 | 0.0206 (4) | 0.0158 (3) | 0.0122 (3) | −0.0029 (3) | 0.0018 (2) | −0.0002 (2) |
C14 | 0.0167 (3) | 0.0161 (3) | 0.0134 (3) | −0.0022 (2) | 0.0027 (2) | 0.0013 (2) |
C15 | 0.0168 (3) | 0.0168 (3) | 0.0126 (3) | −0.0014 (2) | 0.0030 (2) | −0.0002 (2) |
C17 | 0.0274 (5) | 0.0209 (4) | 0.0239 (4) | −0.0083 (3) | 0.0059 (3) | −0.0049 (3) |
C18 | 0.0217 (4) | 0.0221 (4) | 0.0189 (3) | −0.0040 (3) | 0.0079 (3) | 0.0008 (3) |
Geometric parameters (Å, º) top
Cl1—C3 | 1.7386 (8) | C5—C6 | 1.3952 (11) |
O1—C7 | 1.2301 (10) | C5—H5A | 0.9301 |
O2—C12 | 1.3659 (10) | C6—C7 | 1.5002 (11) |
O2—C16 | 1.4318 (15) | C7—C8 | 1.4740 (11) |
C16—H16A | 0.9601 | C8—C9 | 1.3474 (11) |
C16—H16B | 0.9599 | C8—H8A | 0.9299 |
C16—H16C | 0.9600 | C9—C10 | 1.4644 (11) |
Cl2—C12 | 1.913 (6) | C9—H9A | 0.9299 |
Cl2—H16A | 1.2921 | C10—C15 | 1.3994 (12) |
Cl2—H16B | 1.2276 | C10—C11 | 1.4048 (11) |
Cl2—H16C | 1.4426 | C11—C12 | 1.3963 (11) |
O3—C13 | 1.3682 (10) | C11—H11A | 0.9301 |
O3—C17 | 1.4301 (12) | C12—C13 | 1.4012 (12) |
O4—C14 | 1.3638 (11) | C13—C14 | 1.4064 (12) |
O4—C18 | 1.4332 (11) | C14—C15 | 1.3926 (11) |
C1—C6 | 1.3965 (12) | C15—H15A | 0.9300 |
C1—C2 | 1.3970 (12) | C17—H17A | 0.9600 |
C1—H1A | 0.9301 | C17—H17B | 0.9600 |
C2—C3 | 1.3906 (13) | C17—H17C | 0.9601 |
C2—H2A | 0.9300 | C18—H18A | 0.9600 |
C3—C4 | 1.3892 (13) | C18—H18B | 0.9600 |
C4—C5 | 1.3867 (11) | C18—H18C | 0.9601 |
C4—H4A | 0.9300 | | |
| | | |
C12—O2—C16 | 117.05 (7) | C7—C8—H8A | 119.6 |
O2—C16—H16A | 109.5 | C8—C9—C10 | 125.77 (8) |
O2—C16—H16B | 109.5 | C8—C9—H9A | 117.1 |
H16A—C16—H16B | 109.5 | C10—C9—H9A | 117.1 |
O2—C16—H16C | 109.4 | C15—C10—C11 | 119.84 (7) |
H16A—C16—H16C | 109.5 | C15—C10—C9 | 121.83 (7) |
H16B—C16—H16C | 109.5 | C11—C10—C9 | 118.30 (7) |
C12—Cl2—H16A | 166.3 | C12—C11—C10 | 119.74 (8) |
C12—Cl2—H16B | 110.7 | C12—C11—H11A | 120.1 |
H16A—Cl2—H16B | 76.9 | C10—C11—H11A | 120.1 |
C12—Cl2—H16C | 101.3 | O2—C12—C11 | 124.87 (8) |
H16A—Cl2—H16C | 69.7 | O2—C12—C13 | 114.47 (7) |
H16B—Cl2—H16C | 71.4 | C11—C12—C13 | 120.66 (7) |
C13—O3—C17 | 118.57 (7) | O2—C12—Cl2 | 22.09 (18) |
C14—O4—C18 | 116.34 (7) | C11—C12—Cl2 | 103.1 (2) |
C6—C1—C2 | 120.62 (8) | C13—C12—Cl2 | 136.0 (2) |
C6—C1—H1A | 119.7 | O3—C13—C12 | 117.18 (7) |
C2—C1—H1A | 119.7 | O3—C13—C14 | 123.28 (8) |
C3—C2—C1 | 118.76 (8) | C12—C13—C14 | 119.14 (7) |
C3—C2—H2A | 120.6 | O4—C14—C15 | 124.02 (7) |
C1—C2—H2A | 120.6 | O4—C14—C13 | 115.51 (7) |
C4—C3—C2 | 121.49 (8) | C15—C14—C13 | 120.38 (8) |
C4—C3—Cl1 | 118.64 (6) | C14—C15—C10 | 120.16 (7) |
C2—C3—Cl1 | 119.87 (7) | C14—C15—H15A | 119.9 |
C5—C4—C3 | 118.99 (8) | C10—C15—H15A | 119.9 |
C5—C4—H4A | 120.5 | O3—C17—H17A | 109.5 |
C3—C4—H4A | 120.5 | O3—C17—H17B | 109.5 |
C4—C5—C6 | 120.94 (8) | H17A—C17—H17B | 109.5 |
C4—C5—H5A | 119.5 | O3—C17—H17C | 109.4 |
C6—C5—H5A | 119.5 | H17A—C17—H17C | 109.5 |
C5—C6—C1 | 119.14 (7) | H17B—C17—H17C | 109.5 |
C5—C6—C7 | 117.57 (7) | O4—C18—H18A | 109.5 |
C1—C6—C7 | 123.28 (7) | O4—C18—H18B | 109.5 |
O1—C7—C8 | 122.06 (7) | H18A—C18—H18B | 109.5 |
O1—C7—C6 | 119.56 (7) | O4—C18—H18C | 109.5 |
C8—C7—C6 | 118.37 (7) | H18A—C18—H18C | 109.5 |
C9—C8—C7 | 120.89 (8) | H18B—C18—H18C | 109.5 |
C9—C8—H8A | 119.6 | | |
| | | |
C6—C1—C2—C3 | −0.46 (14) | C16—O2—C12—Cl2 | −14.8 (5) |
C1—C2—C3—C4 | 2.00 (14) | C10—C11—C12—O2 | 179.31 (8) |
C1—C2—C3—Cl1 | −177.83 (7) | C10—C11—C12—C13 | −1.44 (13) |
C2—C3—C4—C5 | −1.29 (14) | C10—C11—C12—Cl2 | −176.56 (19) |
Cl1—C3—C4—C5 | 178.54 (7) | C17—O3—C13—C12 | −130.90 (9) |
C3—C4—C5—C6 | −0.99 (13) | C17—O3—C13—C14 | 56.42 (13) |
C4—C5—C6—C1 | 2.49 (13) | O2—C12—C13—O3 | 6.16 (12) |
C4—C5—C6—C7 | −176.99 (8) | C11—C12—C13—O3 | −173.17 (8) |
C2—C1—C6—C5 | −1.74 (14) | Cl2—C12—C13—O3 | 0.0 (3) |
C2—C1—C6—C7 | 177.70 (8) | O2—C12—C13—C14 | 179.15 (8) |
C5—C6—C7—O1 | −16.38 (12) | C11—C12—C13—C14 | −0.18 (13) |
C1—C6—C7—O1 | 164.17 (9) | Cl2—C12—C13—C14 | 173.0 (3) |
C5—C6—C7—C8 | 162.24 (8) | C18—O4—C14—C15 | 3.00 (12) |
C1—C6—C7—C8 | −17.21 (12) | C18—O4—C14—C13 | 179.69 (8) |
O1—C7—C8—C9 | −11.41 (13) | O3—C13—C14—O4 | −1.76 (12) |
C6—C7—C8—C9 | 170.02 (8) | C12—C13—C14—O4 | −174.30 (8) |
C7—C8—C9—C10 | 177.30 (8) | O3—C13—C14—C15 | 175.07 (8) |
C8—C9—C10—C15 | −4.57 (13) | C12—C13—C14—C15 | 2.53 (12) |
C8—C9—C10—C11 | 177.35 (8) | O4—C14—C15—C10 | 173.29 (8) |
C15—C10—C11—C12 | 0.73 (12) | C13—C14—C15—C10 | −3.25 (13) |
C9—C10—C11—C12 | 178.86 (7) | C11—C10—C15—C14 | 1.60 (12) |
C16—O2—C12—C11 | −4.07 (13) | C9—C10—C15—C14 | −176.45 (8) |
C16—O2—C12—C13 | 176.64 (8) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···O1 | 0.93 | 2.51 | 2.829 (1) | 100 |
C17—H17C···O4 | 0.96 | 2.34 | 2.866 (1) | 114 |
C9—H9A···O1i | 0.93 | 2.51 | 3.414 (1) | 166 |
C18—H18C···O1ii | 0.96 | 2.59 | 3.526 (1) | 164 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y, −z+1. |