A cocrystal of 1-(4-methoxy­phen­yl)-3-(3,4,5-trimethoxy­phen­yl)prop-2-en-1-one and (E)-3-(3-chloro-4,5-dimethoxy­phen­yl)-1-(4-methoxy­phen­yl)-2-propen-1-one (0.92/0.08)

Ng, S.-L.; Patil, P.S.; Razak, I.A.; Fun, H.-K.; Dharmaprakash, S.M.

doi:10.1107/S1600536806007239

A cocrystal of 1-(4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one and (E)-3-(3-chloro-4,5-dimethoxyphenyl)-1-(4-methoxyphenyl)-2-propen-1-one (0.92/0.08)

S.-L. Ng, P. S. Patil, I. A. Razak, H.-K. Fun and S. M. Dharmaprakash

In the title compound, 0.92C₁₉H₂₀O₅·0.08C₁₈H₁₇ClO₄, C—H

O and C—H

π interactions link the molecules into a three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007239/ci6758sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007239/ci6758Isup2.hkl Contains datablock I

CCDC reference: 605026

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.001 Å
Disorder in main residue
R factor = 0.043
wR factor = 0.128
Data-to-parameter ratio = 30.5

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.829     0.958
            Tmin(prime) and Tmax expected:      0.930     0.957
            RR(prime) =      0.891
            Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.89
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.65 mm
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms ..          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.32
PLAT301_ALERT_3_C Main Residue  Disorder .........................       8.00 Perc.

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C18.92 H19.77 Cl.08 O4.92
            Atom count from _chemical_formula_moiety:C18.92 H19.76 Cl.08 O4.92
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
            symmetry error - see SYMMG tests
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C18.92 H19.77 Cl0.08 O4.92
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         75.68     75.70   -0.02
           H         79.08     79.09   -0.01
           Cl         4.00      0.30    3.70
           O         19.68     19.70   -0.02

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one–(E)-3-(3-chloro- 4,5-dimethoxyphenyl)-1-(4-methoxyphenyl)-2-propen-1-one (0.92/0.08) top

Crystal data top

0.92C₁₉H₂₀O₅·0.08C₁₈H₁₇ClO₄	F(000) = 696
M_r = 328.69	D_x = 1.360 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6138 reflections
a = 7.4777 (2) Å	θ = 2.5–35.0°
b = 16.1092 (4) Å	µ = 0.11 mm⁻¹
c = 13.7416 (3) Å	T = 120 K
β = 104.043 (1)°	Block, yellow
V = 1605.84 (7) Å³	0.65 × 0.45 × 0.40 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7035 independent reflections
Radiation source: fine-focus sealed tube	5757 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 8.33 pixels mm^-1	θ_max = 35.0°, θ_min = 2.5°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −25→26
T_min = 0.829, T_max = 0.958	l = −21→22
32466 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) = 0.128	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0668P)² + 0.3474P] where P = (F_o² + 2F_c²)/3
7035 reflections	(Δ/σ)_max = 0.001
231 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.21 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	U_iso*/U_eq	Occ. (<1)
Cl1	1.0098 (7)	0.2020 (3)	0.3832 (2)	0.0280 (17)	0.076 (3)
O1	0.19937 (9)	0.02005 (4)	−0.51185 (5)	0.02297 (13)
O2	0.80761 (9)	−0.03265 (4)	−0.10244 (5)	0.02369 (13)
O3	0.93281 (16)	0.22600 (7)	0.36822 (6)	0.02048 (16)	0.924 (3)
O4	0.59970 (11)	0.28319 (4)	0.35088 (5)	0.02743 (15)
O5	0.33073 (9)	0.26521 (4)	0.17709 (5)	0.02238 (13)
C1	0.45007 (11)	0.08818 (5)	−0.26655 (6)	0.01865 (14)
H1	0.4558	0.1354	−0.2269	0.022*
C2	0.33494 (11)	0.08730 (5)	−0.36205 (6)	0.01962 (14)
H2	0.2662	0.1341	−0.3869	0.024*
C3	0.32218 (11)	0.01568 (5)	−0.42129 (6)	0.01794 (14)
C4	0.43174 (12)	−0.05342 (5)	−0.38571 (6)	0.01903 (14)
H4	0.4254	−0.1007	−0.4252	0.023*
C5	0.55018 (11)	−0.05059 (5)	−0.29074 (6)	0.01804 (14)
H5	0.6258	−0.0959	−0.2679	0.022*
C6	0.55844 (10)	0.01875 (5)	−0.22872 (6)	0.01645 (13)
C7	0.67881 (11)	0.01681 (5)	−0.12520 (6)	0.01742 (13)
C8	0.63364 (11)	0.07518 (5)	−0.05139 (6)	0.01949 (14)
H8	0.5209	0.1027	−0.0678	0.023*
C9	0.74901 (11)	0.08998 (5)	0.03827 (6)	0.01779 (14)
H9	0.8627	0.0633	0.0525	0.021*
C10	0.70937 (11)	0.14502 (5)	0.11542 (6)	0.01712 (13)
C11	0.84606 (11)	0.15764 (5)	0.20412 (6)	0.01844 (14)
H11	0.9609	0.1326	0.2125	0.022*
C12	0.80941 (11)	0.20791 (5)	0.27977 (6)	0.01842 (14)
C13	0.63504 (12)	0.24373 (5)	0.26920 (6)	0.01893 (14)
C14	0.49912 (11)	0.23087 (5)	0.18015 (6)	0.01797 (14)
C15	0.53689 (11)	0.18313 (5)	0.10314 (6)	0.01816 (14)
H15	0.4475	0.1765	0.0434	0.022*
C16	0.16695 (13)	−0.05366 (6)	−0.57164 (7)	0.02550 (17)
H16A	0.0724	−0.0432	−0.6315	0.038*
H16B	0.1282	−0.0975	−0.5341	0.038*
H16C	0.2785	−0.0697	−0.5895	0.038*
C17	0.18530 (12)	0.24602 (6)	0.09066 (7)	0.02337 (16)
H17A	0.0737	0.2728	0.0965	0.035*
H17B	0.1666	0.1870	0.0864	0.035*
H17C	0.2184	0.2654	0.0313	0.035*
C18	0.54695 (14)	0.36882 (6)	0.33991 (7)	0.02600 (17)
H18A	0.5510	0.3921	0.4047	0.039*
H18B	0.4240	0.3732	0.2983	0.039*
H18C	0.6305	0.3985	0.3093	0.039*
C19	1.12135 (17)	0.20302 (7)	0.37611 (7)	0.0239 (2)	0.924 (3)
H19A	1.1973	0.2248	0.4374	0.036*	0.924 (3)
H19B	1.1612	0.2253	0.3201	0.036*	0.924 (3)
H19C	1.1315	0.1436	0.3761	0.036*	0.924 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.037 (4)	0.0283 (19)	0.0153 (13)	−0.0015 (17)	−0.0002 (13)	−0.0017 (10)
O1	0.0249 (3)	0.0232 (3)	0.0185 (3)	0.0001 (2)	0.0010 (2)	−0.0045 (2)
O2	0.0209 (3)	0.0204 (3)	0.0273 (3)	0.0047 (2)	0.0011 (2)	−0.0039 (2)
O3	0.0211 (4)	0.0241 (4)	0.0142 (3)	0.0026 (3)	0.0002 (3)	−0.0027 (3)
O4	0.0409 (4)	0.0274 (3)	0.0149 (3)	0.0110 (3)	0.0085 (3)	0.0005 (2)
O5	0.0210 (3)	0.0279 (3)	0.0184 (3)	0.0055 (2)	0.0053 (2)	−0.0020 (2)
C1	0.0198 (3)	0.0154 (3)	0.0206 (3)	0.0011 (2)	0.0044 (3)	−0.0033 (3)
C2	0.0211 (3)	0.0167 (3)	0.0203 (3)	0.0015 (3)	0.0035 (3)	−0.0019 (3)
C3	0.0187 (3)	0.0183 (3)	0.0172 (3)	−0.0018 (2)	0.0051 (2)	−0.0017 (3)
C4	0.0232 (3)	0.0153 (3)	0.0193 (3)	−0.0013 (3)	0.0066 (3)	−0.0029 (3)
C5	0.0204 (3)	0.0145 (3)	0.0201 (3)	0.0004 (2)	0.0068 (3)	−0.0010 (2)
C6	0.0166 (3)	0.0152 (3)	0.0180 (3)	0.0000 (2)	0.0050 (2)	−0.0018 (2)
C7	0.0168 (3)	0.0158 (3)	0.0198 (3)	−0.0007 (2)	0.0048 (3)	−0.0019 (2)
C8	0.0182 (3)	0.0214 (3)	0.0185 (3)	0.0027 (3)	0.0039 (3)	−0.0028 (3)
C9	0.0177 (3)	0.0177 (3)	0.0184 (3)	0.0003 (2)	0.0052 (3)	−0.0008 (3)
C10	0.0181 (3)	0.0173 (3)	0.0163 (3)	−0.0003 (2)	0.0047 (2)	0.0002 (2)
C11	0.0187 (3)	0.0197 (3)	0.0168 (3)	0.0003 (3)	0.0041 (3)	−0.0001 (3)
C12	0.0216 (3)	0.0188 (3)	0.0141 (3)	−0.0010 (3)	0.0030 (3)	0.0014 (2)
C13	0.0250 (4)	0.0185 (3)	0.0139 (3)	0.0027 (3)	0.0060 (3)	0.0013 (2)
C14	0.0200 (3)	0.0188 (3)	0.0160 (3)	0.0022 (2)	0.0061 (3)	0.0016 (2)
C15	0.0195 (3)	0.0199 (3)	0.0156 (3)	0.0011 (3)	0.0053 (2)	−0.0005 (2)
C16	0.0258 (4)	0.0277 (4)	0.0219 (4)	−0.0041 (3)	0.0038 (3)	−0.0086 (3)
C17	0.0201 (3)	0.0247 (4)	0.0246 (4)	0.0026 (3)	0.0041 (3)	−0.0020 (3)
C18	0.0300 (4)	0.0256 (4)	0.0231 (4)	0.0053 (3)	0.0078 (3)	−0.0043 (3)
C19	0.0235 (5)	0.0262 (4)	0.0190 (4)	0.0041 (3)	−0.0007 (3)	−0.0010 (3)

Geometric parameters (Å, º) top

Cl1—C12	1.800 (5)	C8—H8	0.93
O1—C3	1.3573 (10)	C9—C10	1.4665 (11)
O1—C16	1.4308 (11)	C9—H9	0.93
O2—C7	1.2305 (10)	C10—C15	1.4011 (11)
O3—C12	1.3673 (12)	C10—C11	1.4025 (11)
O3—C19	1.4361 (19)	C11—C12	1.3963 (11)
O4—C13	1.3703 (10)	C11—H11	0.93
O4—C18	1.4326 (12)	C12—C13	1.4009 (12)
O5—C14	1.3665 (10)	C13—C14	1.4035 (12)
O5—C17	1.4359 (11)	C14—C15	1.3916 (11)
C1—C2	1.3839 (12)	C15—H15	0.93
C1—C6	1.4048 (11)	C16—H16A	0.96
C1—H1	0.93	C16—H16B	0.96
C2—C3	1.4017 (11)	C16—H16C	0.96
C2—H2	0.93	C17—H17A	0.96
C3—C4	1.3982 (12)	C17—H17B	0.96
C4—C5	1.3888 (12)	C17—H17C	0.96
C4—H4	0.93	C18—H18A	0.96
C5—C6	1.3973 (11)	C18—H18B	0.96
C5—H5	0.93	C18—H18C	0.96
C6—C7	1.4877 (11)	C19—H19A	0.96
C7—C8	1.4810 (11)	C19—H19B	0.96
C8—C9	1.3428 (11)	C19—H19C	0.96

C3—O1—C16	117.78 (7)	C12—C11—H11	120.1
C12—O3—C19	116.78 (8)	C10—C11—H11	120.1
C13—O4—C18	117.60 (7)	O3—C12—C11	124.99 (8)
C14—O5—C17	116.46 (7)	O3—C12—C13	114.50 (8)
C2—C1—C6	120.86 (7)	C11—C12—C13	120.50 (7)
C2—C1—H1	119.6	C11—C12—Cl1	106.32 (16)
C6—C1—H1	119.6	C13—C12—Cl1	132.78 (16)
C1—C2—C3	119.88 (7)	O4—C13—C12	117.77 (7)
C1—C2—H2	120.1	O4—C13—C14	122.67 (7)
C3—C2—H2	120.1	C12—C13—C14	119.24 (7)
O1—C3—C4	124.78 (7)	O5—C14—C15	123.77 (7)
O1—C3—C2	115.17 (7)	O5—C14—C13	115.72 (7)
C4—C3—C2	120.05 (8)	C15—C14—C13	120.46 (7)
C5—C4—C3	119.23 (7)	C14—C15—C10	120.09 (7)
C5—C4—H4	120.4	C14—C15—H15	120.0
C3—C4—H4	120.4	C10—C15—H15	120.0
C4—C5—C6	121.54 (7)	O1—C16—H16A	109.5
C4—C5—H5	119.2	O1—C16—H16B	109.5
C6—C5—H5	119.2	H16A—C16—H16B	109.5
C5—C6—C1	118.33 (7)	O1—C16—H16C	109.5
C5—C6—C7	119.56 (7)	H16A—C16—H16C	109.5
C1—C6—C7	122.10 (7)	H16B—C16—H16C	109.5
O2—C7—C8	122.11 (8)	O5—C17—H17A	109.5
O2—C7—C6	120.75 (7)	O5—C17—H17B	109.5
C8—C7—C6	117.12 (7)	H17A—C17—H17B	109.5
C9—C8—C7	122.59 (7)	O5—C17—H17C	109.5
C9—C8—H8	118.7	H17A—C17—H17C	109.5
C7—C8—H8	118.7	H17B—C17—H17C	109.5
C8—C9—C10	124.97 (7)	O4—C18—H18A	109.5
C8—C9—H9	117.5	O4—C18—H18B	109.5
C10—C9—H9	117.5	H18A—C18—H18B	109.5
C15—C10—C11	119.78 (7)	O4—C18—H18C	109.5
C15—C10—C9	121.29 (7)	H18A—C18—H18C	109.5
C11—C10—C9	118.91 (7)	H18B—C18—H18C	109.5
C12—C11—C10	119.85 (7)

C6—C1—C2—C3	1.59 (12)	C19—O3—C12—C11	10.95 (13)
C16—O1—C3—C4	5.99 (12)	C19—O3—C12—C13	−169.68 (8)
C16—O1—C3—C2	−174.06 (8)	C10—C11—C12—O3	−178.57 (8)
C1—C2—C3—O1	177.18 (7)	C10—C11—C12—C13	2.09 (12)
C1—C2—C3—C4	−2.87 (12)	C10—C11—C12—Cl1	175.71 (13)
O1—C3—C4—C5	−178.92 (7)	C18—O4—C13—C12	122.15 (9)
C2—C3—C4—C5	1.13 (12)	C18—O4—C13—C14	−64.39 (11)
C3—C4—C5—C6	1.93 (12)	O3—C12—C13—O4	−7.87 (11)
C4—C5—C6—C1	−3.18 (12)	C11—C12—C13—O4	171.53 (8)
C4—C5—C6—C7	176.18 (7)	Cl1—C12—C13—O4	−0.1 (2)
C2—C1—C6—C5	1.39 (12)	O3—C12—C13—C14	178.44 (8)
C2—C1—C6—C7	−177.95 (7)	C11—C12—C13—C14	−2.16 (12)
C5—C6—C7—O2	20.78 (12)	Cl1—C12—C13—C14	−173.81 (17)
C1—C6—C7—O2	−159.88 (8)	C17—O5—C14—C15	3.35 (12)
C5—C6—C7—C8	−157.78 (7)	C17—O5—C14—C13	−174.21 (7)
C1—C6—C7—C8	21.56 (11)	O4—C13—C14—O5	4.26 (12)
O2—C7—C8—C9	13.67 (13)	C12—C13—C14—O5	177.63 (7)
C6—C7—C8—C9	−167.79 (8)	O4—C13—C14—C15	−173.38 (8)
C7—C8—C9—C10	−178.01 (7)	C12—C13—C14—C15	−0.02 (12)
C8—C9—C10—C15	4.50 (13)	O5—C14—C15—C10	−175.19 (8)
C8—C9—C10—C11	−177.19 (8)	C13—C14—C15—C10	2.26 (12)
C15—C10—C11—C12	0.17 (12)	C11—C10—C15—C14	−2.33 (12)
C9—C10—C11—C12	−178.17 (7)	C9—C10—C15—C14	175.96 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2ⁱ	0.93	2.44	3.3472 (11)	164
C17—H17B···O2ⁱⁱ	0.96	2.50	3.4408 (12)	166
C17—H17C···O4ⁱⁱⁱ	0.96	2.54	3.2349 (12)	129
C18—H18B···O5	0.96	2.39	2.9411 (12)	116
C19—H19C···O1^iv	0.96	2.49	3.3110 (13)	143
C16—H16C···Cg1^v	0.96	2.76	3.5927 (11)	145

Symmetry codes: (i) −x+2, −y, −z; (ii) −x+1, −y, −z; (iii) x−1/2, −y+1/2, z−1/2; (iv) x+1, y, z+1; (v) −x+1, −y, −z−1.

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A cocrystal of 1-(4-methoxy­phen­yl)-3-(3,4,5-trimethoxy­phen­yl)prop-2-en-1-one and (E)-3-(3-chloro-4,5-dimethoxy­phen­yl)-1-(4-methoxy­phen­yl)-2-propen-1-one (0.92/0.08)

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A cocrystal of 1-(4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one and (E)-3-(3-chloro-4,5-dimethoxyphenyl)-1-(4-methoxyphenyl)-2-propen-1-one (0.92/0.08)