1-(4-Chloro­phen­yl)-3-(2,4,5-trimethoxy­phen­yl)prop-2-en-1-one

Teh, J.B.-J.; Patil, P.S.; Fun, H.-K.; Razak, I.A.; Dharmaprakash, S.M.

doi:10.1107/S1600536806023191

1-(4-Chlorophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one

J. B.-J. Teh, P. S. Patil, H.-K. Fun, I. A. Razak and S. M. Dharmaprakash

In the title compound, C₁₈H₁₆Cl₂O₄, the dihedral angle between the benzene rings is 65.9 (1)°. The crystal packing is stabilized by intermolecular C—H

O interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806023191/fl2032sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806023191/fl2032Isup2.hkl Contains datablock I

CCDC reference: 613682

checkCIF report

Key indicators

Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.002 Å
R factor = 0.054
wR factor = 0.178
Data-to-parameter ratio = 34.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.34

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 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-Chlorophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₈H₁₆Cl₂O₄	Z = 2
M_r = 367.21	F(000) = 380
Triclinic, P1	D_x = 1.405 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4985 (1) Å	Cell parameters from 7354 reflections
b = 9.3394 (2) Å	θ = 2.5–35.0°
c = 11.4856 (2) Å	µ = 0.39 mm⁻¹
α = 83.199 (1)°	T = 297 K
β = 74.701 (1)°	Block, yellow
γ = 82.419 (1)°	0.41 × 0.38 × 0.29 mm
V = 868.29 (3) Å³

Data collection top

Brucker SMART APEX2 CCD area-detector diffractometer	7577 independent reflections
Radiation source: fine-focus sealed tube	4710 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 8.33 pixels mm^-1	θ_max = 35.0°, θ_min = 2.5°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −14→15
T_min = 0.816, T_max = 0.895	l = −18→18
18803 measured reflections

Refinement top

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)] = 0.054	H-atom parameters constrained
wR(F²) = 0.178	w = 1/[σ²(F_o²) + (0.0838P)² + 0.1675P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
7577 reflections	Δρ_max = 0.65 e Å⁻³
221 parameters	Δρ_min = −0.47 e Å⁻³
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.045 (5)

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
Cl1	0.52251 (6)	0.72438 (5)	0.08214 (5)	0.06765 (16)
Cl2	0.95400 (8)	0.38434 (7)	−0.22189 (4)	0.0825 (2)
O1	0.29504 (18)	0.09872 (15)	0.21394 (10)	0.0646 (4)
O2	0.13395 (15)	−0.20217 (11)	0.59043 (10)	0.0535 (3)
O3	0.22937 (15)	−0.02397 (12)	0.70496 (9)	0.0524 (3)
O4	0.5997 (3)	0.60235 (17)	0.32927 (13)	0.0980 (7)
C1	0.28089 (18)	0.06510 (15)	0.33547 (12)	0.0436 (3)
C2	0.20904 (18)	−0.05736 (16)	0.39870 (13)	0.0453 (3)
H2A	0.1693	−0.1196	0.3584	0.054*
C3	0.19764 (16)	−0.08505 (14)	0.52149 (12)	0.0417 (3)
C4	0.25229 (16)	0.01179 (14)	0.58327 (11)	0.0392 (3)
C5	0.32665 (16)	0.12973 (14)	0.51932 (12)	0.0397 (3)
H5A	0.3652	0.1924	0.5600	0.048*
C6	0.34536 (16)	0.15700 (14)	0.39333 (11)	0.0402 (3)
C7	0.43704 (17)	0.27306 (15)	0.32205 (12)	0.0427 (3)
H7A	0.4648	0.2708	0.2383	0.051*
C8	0.4853 (2)	0.38234 (16)	0.36500 (13)	0.0529 (4)
H8A	0.4544	0.3891	0.4483	0.063*
C9	0.5836 (3)	0.49182 (17)	0.28869 (14)	0.0575 (4)
C10	0.67078 (19)	0.46607 (15)	0.15972 (12)	0.0451 (3)
C11	0.65620 (18)	0.56705 (15)	0.06241 (13)	0.0439 (3)
C12	0.74426 (19)	0.54386 (16)	−0.05514 (12)	0.0483 (3)
H12A	0.7332	0.6117	−0.1194	0.058*
C13	0.8483 (2)	0.41823 (18)	−0.07462 (13)	0.0502 (3)
C14	0.8682 (2)	0.31696 (18)	0.01945 (15)	0.0539 (4)
H14A	0.9406	0.2335	0.0048	0.065*
C15	0.7786 (2)	0.34170 (16)	0.13591 (13)	0.0516 (4)
H15A	0.7909	0.2735	0.1997	0.062*
C16	0.2018 (3)	0.0319 (2)	0.15686 (16)	0.0623 (4)
H16A	0.2167	0.0728	0.0745	0.093*
H16B	0.0880	0.0471	0.1988	0.093*
H16C	0.2364	−0.0703	0.1581	0.093*
C17	0.0952 (3)	−0.3121 (2)	0.52903 (19)	0.0689 (5)
H17A	0.0598	−0.3922	0.5863	0.103*
H17B	0.1908	−0.3448	0.4687	0.103*
H17C	0.0091	−0.2732	0.4908	0.103*
C18	0.2917 (2)	0.06401 (18)	0.77087 (14)	0.0561 (4)
H18A	0.2722	0.0250	0.8540	0.084*
H18B	0.2376	0.1607	0.7666	0.084*
H18C	0.4074	0.0660	0.7368	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0719 (3)	0.0504 (2)	0.0760 (3)	−0.00265 (19)	−0.0161 (2)	0.00320 (19)
Cl2	0.0964 (4)	0.0887 (4)	0.0456 (2)	−0.0116 (3)	0.0089 (2)	0.0019 (2)
O1	0.0839 (8)	0.0806 (8)	0.0362 (5)	−0.0424 (7)	−0.0208 (5)	0.0180 (5)
O2	0.0701 (7)	0.0469 (5)	0.0450 (5)	−0.0263 (5)	−0.0161 (5)	0.0169 (4)
O3	0.0727 (7)	0.0504 (5)	0.0339 (5)	−0.0230 (5)	−0.0123 (5)	0.0128 (4)
O4	0.1785 (19)	0.0661 (8)	0.0458 (7)	−0.0676 (11)	0.0044 (9)	−0.0048 (6)
C1	0.0476 (7)	0.0482 (7)	0.0336 (6)	−0.0142 (5)	−0.0095 (5)	0.0111 (5)
C2	0.0504 (7)	0.0475 (7)	0.0390 (6)	−0.0175 (6)	−0.0125 (5)	0.0093 (5)
C3	0.0420 (6)	0.0402 (6)	0.0398 (6)	−0.0110 (5)	−0.0090 (5)	0.0128 (5)
C4	0.0413 (6)	0.0396 (6)	0.0326 (5)	−0.0067 (5)	−0.0068 (4)	0.0102 (4)
C5	0.0439 (6)	0.0376 (5)	0.0355 (6)	−0.0098 (5)	−0.0083 (5)	0.0080 (4)
C6	0.0432 (6)	0.0397 (6)	0.0343 (6)	−0.0098 (5)	−0.0074 (5)	0.0104 (4)
C7	0.0478 (7)	0.0415 (6)	0.0348 (6)	−0.0108 (5)	−0.0066 (5)	0.0109 (5)
C8	0.0732 (10)	0.0453 (7)	0.0341 (6)	−0.0204 (7)	−0.0007 (6)	0.0068 (5)
C9	0.0877 (12)	0.0473 (7)	0.0358 (6)	−0.0297 (8)	−0.0060 (7)	0.0062 (5)
C10	0.0589 (8)	0.0435 (6)	0.0338 (6)	−0.0225 (6)	−0.0105 (5)	0.0099 (5)
C11	0.0502 (7)	0.0411 (6)	0.0413 (6)	−0.0155 (5)	−0.0138 (5)	0.0099 (5)
C12	0.0579 (8)	0.0505 (7)	0.0376 (6)	−0.0178 (6)	−0.0165 (6)	0.0149 (5)
C13	0.0533 (8)	0.0580 (8)	0.0368 (6)	−0.0173 (6)	−0.0072 (6)	0.0090 (6)
C14	0.0555 (9)	0.0513 (8)	0.0506 (8)	−0.0061 (6)	−0.0119 (7)	0.0095 (6)
C15	0.0670 (9)	0.0471 (7)	0.0408 (7)	−0.0149 (7)	−0.0179 (6)	0.0154 (6)
C16	0.0720 (11)	0.0771 (11)	0.0423 (8)	−0.0227 (9)	−0.0191 (7)	0.0046 (7)
C17	0.0961 (14)	0.0508 (9)	0.0646 (11)	−0.0328 (9)	−0.0244 (10)	0.0129 (8)
C18	0.0773 (11)	0.0520 (8)	0.0379 (7)	−0.0135 (7)	−0.0116 (7)	0.0019 (6)

Geometric parameters (Å, º) top

Cl1—C11	1.7331 (16)	C8—H8A	0.9300
Cl2—C13	1.7373 (16)	C9—C10	1.503 (2)
O1—C1	1.3707 (16)	C10—C15	1.388 (2)
O1—C16	1.396 (2)	C10—C11	1.3952 (18)
O2—C3	1.3569 (14)	C11—C12	1.387 (2)
O2—C17	1.429 (2)	C12—C13	1.376 (2)
O3—C4	1.3659 (15)	C12—H12A	0.9300
O3—C18	1.415 (2)	C13—C14	1.379 (2)
O4—C9	1.219 (2)	C14—C15	1.383 (2)
C1—C6	1.389 (2)	C14—H14A	0.9300
C1—C2	1.4007 (17)	C15—H15A	0.9300
C2—C3	1.3833 (19)	C16—H16A	0.9600
C2—H2A	0.9300	C16—H16B	0.9600
C3—C4	1.405 (2)	C16—H16C	0.9600
C4—C5	1.3782 (16)	C17—H17A	0.9600
C5—C6	1.4093 (17)	C17—H17B	0.9600
C5—H5A	0.9300	C17—H17C	0.9600
C6—C7	1.4589 (16)	C18—H18A	0.9600
C7—C8	1.338 (2)	C18—H18B	0.9600
C7—H7A	0.9300	C18—H18C	0.9600
C8—C9	1.4626 (19)

C1—O1—C16	119.10 (12)	C12—C11—C10	121.46 (14)
C3—O2—C17	117.34 (12)	C12—C11—Cl1	116.92 (10)
C4—O3—C18	117.70 (11)	C10—C11—Cl1	121.58 (12)
O1—C1—C6	116.64 (11)	C13—C12—C11	118.52 (12)
O1—C1—C2	122.29 (13)	C13—C12—H12A	120.7
C6—C1—C2	121.05 (12)	C11—C12—H12A	120.7
C3—C2—C1	119.55 (13)	C12—C13—C14	121.73 (15)
C3—C2—H2A	120.2	C12—C13—Cl2	119.14 (11)
C1—C2—H2A	120.2	C14—C13—Cl2	119.11 (14)
O2—C3—C2	124.23 (13)	C13—C14—C15	118.87 (16)
O2—C3—C4	115.53 (12)	C13—C14—H14A	120.6
C2—C3—C4	120.23 (11)	C15—C14—H14A	120.6
O3—C4—C5	125.44 (13)	C14—C15—C10	121.42 (13)
O3—C4—C3	115.03 (10)	C14—C15—H15A	119.3
C5—C4—C3	119.50 (12)	C10—C15—H15A	119.3
C4—C5—C6	121.17 (13)	O1—C16—H16A	109.5
C4—C5—H5A	119.4	O1—C16—H16B	109.5
C6—C5—H5A	119.4	H16A—C16—H16B	109.5
C1—C6—C5	118.30 (11)	O1—C16—H16C	109.5
C1—C6—C7	119.57 (12)	H16A—C16—H16C	109.5
C5—C6—C7	122.06 (12)	H16B—C16—H16C	109.5
C8—C7—C6	126.56 (13)	O2—C17—H17A	109.5
C8—C7—H7A	116.7	O2—C17—H17B	109.5
C6—C7—H7A	116.7	H17A—C17—H17B	109.5
C7—C8—C9	123.84 (13)	O2—C17—H17C	109.5
C7—C8—H8A	118.1	H17A—C17—H17C	109.5
C9—C8—H8A	118.1	H17B—C17—H17C	109.5
O4—C9—C8	120.84 (15)	O3—C18—H18A	109.5
O4—C9—C10	119.32 (13)	O3—C18—H18B	109.5
C8—C9—C10	119.80 (13)	H18A—C18—H18B	109.5
C15—C10—C11	117.98 (13)	O3—C18—H18C	109.5
C15—C10—C9	119.30 (13)	H18A—C18—H18C	109.5
C11—C10—C9	122.58 (15)	H18B—C18—H18C	109.5

C16—O1—C1—C6	−165.59 (16)	C1—C6—C7—C8	169.38 (16)
C16—O1—C1—C2	16.0 (3)	C5—C6—C7—C8	−13.9 (2)
O1—C1—C2—C3	−179.69 (15)	C6—C7—C8—C9	177.08 (16)
C6—C1—C2—C3	1.9 (2)	C7—C8—C9—O4	167.0 (2)
C17—O2—C3—C2	8.0 (2)	C7—C8—C9—C10	−15.1 (3)
C17—O2—C3—C4	−172.63 (15)	O4—C9—C10—C15	122.2 (2)
C1—C2—C3—O2	−178.38 (14)	C8—C9—C10—C15	−55.7 (2)
C1—C2—C3—C4	2.3 (2)	O4—C9—C10—C11	−53.5 (3)
C18—O3—C4—C5	−2.3 (2)	C8—C9—C10—C11	128.58 (17)
C18—O3—C4—C3	175.90 (14)	C15—C10—C11—C12	1.0 (2)
O2—C3—C4—O3	−1.68 (19)	C9—C10—C11—C12	176.75 (14)
C2—C3—C4—O3	177.69 (14)	C15—C10—C11—Cl1	178.93 (11)
O2—C3—C4—C5	176.60 (13)	C9—C10—C11—Cl1	−5.3 (2)
C2—C3—C4—C5	−4.0 (2)	C10—C11—C12—C13	−0.3 (2)
O3—C4—C5—C6	179.64 (13)	Cl1—C11—C12—C13	−178.29 (11)
C3—C4—C5—C6	1.6 (2)	C11—C12—C13—C14	−0.9 (2)
O1—C1—C6—C5	177.20 (14)	C11—C12—C13—Cl2	177.71 (11)
C2—C1—C6—C5	−4.3 (2)	C12—C13—C14—C15	1.2 (2)
O1—C1—C6—C7	−6.0 (2)	Cl2—C13—C14—C15	−177.37 (13)
C2—C1—C6—C7	172.48 (14)	C13—C14—C15—C10	−0.4 (2)
C4—C5—C6—C1	2.6 (2)	C11—C10—C15—C14	−0.7 (2)
C4—C5—C6—C7	−174.15 (13)	C9—C10—C15—C14	−176.53 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O4ⁱ	0.93	2.51	3.420 (2)	165
C7—H7A···O1	0.93	2.38	2.727 (2)	102
C8—H8A···O4ⁱ	0.93	2.48	3.410 (2)	174
C15—H15A···O3ⁱⁱ	0.93	2.46	3.295 (2)	149

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1.

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1-(4-Chloro­phen­yl)-3-(2,4,5-trimethoxy­phen­yl)prop-2-en-1-one

Supporting information

Key indicators

checkCIF/PLATON results

1-(4-Chlorophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one