(2E)-1-(2,4-Dichloro-phen-yl)-3-(3,4,5-trimeth-oxy-phen-yl)prop-2-en-1-one.

In the title compound, C(18)H(16)Cl(2)O(4), the dihedral angle between the benzene rings is 82.40 (4)°. The meth-oxy groups at both meta positions of the 3,4,5-trimeth-oxy-phenyl ring are slightly twisted from the aromatic ring [C-O-C-C = -166.60 (8) and -6.18 (13)°], whereas the meth-oxy group at the para position is almost perpendicular [C-O-C-C = 112.08 (9)°]. The ketone O atom is connected to the 2,4-dichloro-phenyl group through a C(ar)-C(ar)-C-O (ar = aromatic) torsion angle of -116.43 (9)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds into infinite chains along the b axis. The crystal structure also features C-H⋯π inter-actions.

Related literature

For a related structure, see: Fun et al. (2012 ▶). For background to various chalcone derivatives, see: Samshuddin et al. (2011 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C18H16Cl2O4

M = 367.21

Orthorhombic,

a = 9.4305 (5) Å

b = 13.9334 (8) Å

c = 25.6417 (14) Å

V = 3369.3 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.40 mm−1

T = 100 K

0.48 × 0.39 × 0.22 mm

Data collection

Bruker APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.829, T max = 0.917

24763 measured reflections

6139 independent reflections

5445 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.086

S = 1.03

6139 reflections

220 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812016339/hb6742sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016339/hb6742Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812016339/hb6742Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H16Cl2O4	F(000) = 1520
Mr = 367.21	Dx = 1.448 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9912 reflections
a = 9.4305 (5) Å	θ = 2.7–32.7°
b = 13.9334 (8) Å	µ = 0.40 mm−1
c = 25.6417 (14) Å	T = 100 K
V = 3369.3 (3) Å3	Block, colourless
Z = 8	0.48 × 0.39 × 0.22 mm

Bruker APEX DUO CCD diffractometer	6139 independent reflections
Radiation source: fine-focus sealed tube	5445 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 32.7°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→14
Tmin = 0.829, Tmax = 0.917	k = −20→21
24763 measured reflections	l = −38→35

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0458P)2 + 1.108P] where P = (Fo2 + 2Fc2)/3
6139 reflections	(Δ/σ)max = 0.002
220 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1	0.28135 (3)	0.217251 (16)	0.611803 (9)	0.02108 (6)
Cl2	0.68551 (3)	0.053651 (17)	0.730224 (9)	0.02548 (6)
O1	0.85362 (8)	0.59918 (5)	0.48151 (3)	0.02017 (13)
O2	0.81150 (7)	0.78269 (5)	0.51372 (3)	0.01807 (13)
O3	0.67985 (7)	0.82227 (5)	0.60144 (3)	0.01813 (13)
O4	0.22886 (7)	0.40914 (5)	0.67797 (3)	0.01916 (13)
C1	0.41001 (9)	0.22749 (6)	0.65990 (3)	0.01458 (14)
C2	0.48428 (10)	0.14561 (6)	0.67434 (3)	0.01770 (15)
H2A	0.4638	0.0865	0.6593	0.021*
C3	0.58992 (10)	0.15424 (6)	0.71183 (3)	0.01775 (16)
C4	0.62109 (11)	0.24156 (7)	0.73518 (4)	0.02006 (17)
H4A	0.6907	0.2458	0.7608	0.024*
C5	0.54655 (10)	0.32244 (6)	0.71967 (3)	0.01803 (16)
H5A	0.5680	0.3815	0.7346	0.022*
C6	0.43967 (9)	0.31692 (6)	0.68200 (3)	0.01377 (14)
C7	0.35648 (9)	0.40595 (6)	0.66920 (3)	0.01436 (14)
C8	0.43334 (9)	0.48838 (6)	0.64771 (3)	0.01531 (14)
H8A	0.3917	0.5488	0.6498	0.018*
C9	0.56145 (9)	0.48055 (6)	0.62511 (3)	0.01455 (14)
H9A	0.6055	0.4208	0.6259	0.017*
C10	0.63649 (9)	0.55929 (6)	0.59932 (3)	0.01371 (14)
C11	0.72028 (9)	0.53747 (6)	0.55583 (3)	0.01506 (14)
H11A	0.7355	0.4739	0.5462	0.018*
C12	0.78076 (9)	0.61202 (6)	0.52700 (3)	0.01442 (14)
C13	0.76521 (9)	0.70727 (6)	0.54348 (3)	0.01393 (14)
C14	0.68727 (9)	0.72740 (6)	0.58881 (3)	0.01376 (14)
C15	0.62042 (9)	0.65414 (6)	0.61624 (3)	0.01450 (14)
H15A	0.5657	0.6680	0.6455	0.017*
C16	0.84445 (12)	0.50620 (8)	0.45782 (4)	0.02523 (19)
H16A	0.8912	0.5074	0.4246	0.038*
H16B	0.7466	0.4893	0.4531	0.038*
H16C	0.8894	0.4597	0.4799	0.038*
C17	0.96130 (10)	0.79619 (7)	0.51322 (4)	0.02343 (18)
H17A	0.9849	0.8475	0.4898	0.035*
H17B	1.0066	0.7382	0.5018	0.035*
H17C	0.9933	0.8119	0.5477	0.035*
C18	0.58610 (11)	0.84829 (7)	0.64272 (4)	0.0248 (2)
H18A	0.5853	0.9168	0.6465	0.037*
H18B	0.6178	0.8194	0.6746	0.037*
H18C	0.4921	0.8262	0.6348	0.037*

	U11	U22	U33	U12	U13	U23
Cl1	0.02216 (11)	0.01837 (10)	0.02271 (10)	−0.00144 (8)	−0.00764 (8)	−0.00429 (7)
Cl2	0.03293 (13)	0.02033 (11)	0.02319 (11)	0.00754 (9)	−0.00281 (9)	0.00501 (8)
O1	0.0237 (3)	0.0184 (3)	0.0184 (3)	−0.0001 (3)	0.0076 (2)	−0.0007 (2)
O2	0.0143 (3)	0.0170 (3)	0.0229 (3)	−0.0021 (2)	0.0016 (2)	0.0081 (2)
O3	0.0185 (3)	0.0108 (3)	0.0251 (3)	−0.0023 (2)	0.0047 (2)	−0.0020 (2)
O4	0.0144 (3)	0.0186 (3)	0.0245 (3)	−0.0026 (2)	0.0027 (2)	−0.0016 (2)
C1	0.0158 (3)	0.0142 (3)	0.0137 (3)	−0.0028 (3)	−0.0004 (3)	−0.0005 (3)
C2	0.0225 (4)	0.0133 (3)	0.0173 (3)	−0.0006 (3)	0.0001 (3)	−0.0006 (3)
C3	0.0217 (4)	0.0151 (3)	0.0164 (3)	0.0015 (3)	0.0003 (3)	0.0035 (3)
C4	0.0227 (4)	0.0185 (4)	0.0190 (4)	−0.0014 (3)	−0.0058 (3)	0.0018 (3)
C5	0.0210 (4)	0.0147 (3)	0.0184 (4)	−0.0036 (3)	−0.0036 (3)	0.0000 (3)
C6	0.0148 (3)	0.0122 (3)	0.0143 (3)	−0.0027 (3)	0.0010 (3)	0.0011 (2)
C7	0.0153 (3)	0.0132 (3)	0.0146 (3)	−0.0027 (3)	0.0003 (3)	−0.0011 (3)
C8	0.0148 (3)	0.0118 (3)	0.0193 (4)	−0.0006 (3)	0.0017 (3)	0.0018 (3)
C9	0.0148 (3)	0.0122 (3)	0.0167 (3)	−0.0004 (3)	0.0006 (3)	0.0019 (3)
C10	0.0127 (3)	0.0117 (3)	0.0168 (3)	0.0002 (3)	0.0008 (3)	0.0024 (3)
C11	0.0144 (3)	0.0128 (3)	0.0180 (3)	0.0016 (3)	0.0017 (3)	0.0017 (3)
C12	0.0130 (3)	0.0151 (3)	0.0152 (3)	0.0013 (3)	0.0017 (3)	0.0017 (3)
C13	0.0117 (3)	0.0133 (3)	0.0168 (3)	−0.0003 (3)	0.0006 (3)	0.0035 (3)
C14	0.0120 (3)	0.0111 (3)	0.0182 (3)	−0.0006 (3)	−0.0002 (3)	0.0003 (3)
C15	0.0138 (3)	0.0127 (3)	0.0170 (3)	−0.0009 (3)	0.0023 (3)	0.0006 (3)
C16	0.0312 (5)	0.0230 (4)	0.0216 (4)	−0.0004 (4)	0.0065 (4)	−0.0058 (3)
C17	0.0156 (4)	0.0213 (4)	0.0334 (5)	−0.0034 (3)	0.0058 (3)	0.0033 (4)
C18	0.0246 (5)	0.0164 (4)	0.0334 (5)	−0.0007 (3)	0.0092 (4)	−0.0067 (3)

Cl1—C1	1.7360 (9)	C8—H8A	0.9300
Cl2—C3	1.7319 (9)	C9—C10	1.4635 (11)
O1—C12	1.3655 (10)	C9—H9A	0.9300
O1—C16	1.4334 (12)	C10—C15	1.3992 (11)
O2—C13	1.3702 (10)	C10—C11	1.4000 (12)
O2—C17	1.4252 (11)	C11—C12	1.3967 (12)
O3—C14	1.3628 (10)	C11—H11A	0.9300
O3—C18	1.4260 (12)	C12—C13	1.4005 (12)
O4—C7	1.2252 (11)	C13—C14	1.4034 (12)
C1—C2	1.3890 (12)	C14—C15	1.3909 (11)
C1—C6	1.3971 (11)	C15—H15A	0.9300
C2—C3	1.3896 (13)	C16—H16A	0.9600
C2—H2A	0.9300	C16—H16B	0.9600
C3—C4	1.3874 (13)	C16—H16C	0.9600
C4—C5	1.3864 (13)	C17—H17A	0.9600
C4—H4A	0.9300	C17—H17B	0.9600
C5—C6	1.3983 (12)	C17—H17C	0.9600
C5—H5A	0.9300	C18—H18A	0.9600
C6—C7	1.5040 (12)	C18—H18B	0.9600
C7—C8	1.4658 (12)	C18—H18C	0.9600
C8—C9	1.3444 (12)
C12—O1—C16	116.75 (7)	C12—C11—C10	119.38 (8)
C13—O2—C17	114.96 (7)	C12—C11—H11A	120.3
C14—O3—C18	117.06 (7)	C10—C11—H11A	120.3
C2—C1—C6	121.57 (8)	O1—C12—C11	124.07 (8)
C2—C1—Cl1	118.31 (6)	O1—C12—C13	115.76 (7)
C6—C1—Cl1	120.09 (6)	C11—C12—C13	120.15 (8)
C1—C2—C3	118.35 (8)	O2—C13—C12	121.69 (8)
C1—C2—H2A	120.8	O2—C13—C14	118.34 (7)
C3—C2—H2A	120.8	C12—C13—C14	119.62 (7)
C4—C3—C2	121.75 (8)	O3—C14—C15	124.64 (8)
C4—C3—Cl2	118.81 (7)	O3—C14—C13	114.69 (7)
C2—C3—Cl2	119.44 (7)	C15—C14—C13	120.63 (8)
C5—C4—C3	118.79 (8)	C14—C15—C10	119.16 (8)
C5—C4—H4A	120.6	C14—C15—H15A	120.4
C3—C4—H4A	120.6	C10—C15—H15A	120.4
C4—C5—C6	121.26 (8)	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	118.26 (8)	O1—C16—H16C	109.5
C1—C6—C7	122.87 (7)	H16A—C16—H16C	109.5
C5—C6—C7	118.78 (7)	H16B—C16—H16C	109.5
O4—C7—C8	121.76 (8)	O2—C17—H17A	109.5
O4—C7—C6	120.16 (8)	O2—C17—H17B	109.5
C8—C7—C6	118.06 (7)	H17A—C17—H17B	109.5
C9—C8—C7	122.88 (8)	O2—C17—H17C	109.5
C9—C8—H8A	118.6	H17A—C17—H17C	109.5
C7—C8—H8A	118.6	H17B—C17—H17C	109.5
C8—C9—C10	124.64 (8)	O3—C18—H18A	109.5
C8—C9—H9A	117.7	O3—C18—H18B	109.5
C10—C9—H9A	117.7	H18A—C18—H18B	109.5
C15—C10—C11	120.88 (7)	O3—C18—H18C	109.5
C15—C10—C9	121.04 (7)	H18A—C18—H18C	109.5
C11—C10—C9	118.03 (7)	H18B—C18—H18C	109.5
C6—C1—C2—C3	0.19 (13)	C15—C10—C11—C12	−4.30 (13)
Cl1—C1—C2—C3	178.29 (7)	C9—C10—C11—C12	173.10 (8)
C1—C2—C3—C4	0.71 (14)	C16—O1—C12—C11	11.64 (13)
C1—C2—C3—Cl2	−179.40 (7)	C16—O1—C12—C13	−166.60 (8)
C2—C3—C4—C5	−1.43 (14)	C10—C11—C12—O1	−174.04 (8)
Cl2—C3—C4—C5	178.69 (7)	C10—C11—C12—C13	4.13 (13)
C3—C4—C5—C6	1.26 (14)	C17—O2—C13—C12	−74.72 (11)
C2—C1—C6—C5	−0.34 (13)	C17—O2—C13—C14	112.08 (9)
Cl1—C1—C6—C5	−178.41 (7)	O1—C12—C13—O2	4.53 (12)
C2—C1—C6—C7	−176.86 (8)	C11—C12—C13—O2	−173.79 (8)
Cl1—C1—C6—C7	5.07 (11)	O1—C12—C13—C14	177.64 (8)
C4—C5—C6—C1	−0.39 (13)	C11—C12—C13—C14	−0.67 (13)
C4—C5—C6—C7	176.27 (8)	C18—O3—C14—C15	−6.18 (13)
C1—C6—C7—O4	60.07 (12)	C18—O3—C14—C13	171.48 (8)
C5—C6—C7—O4	−116.43 (9)	O2—C13—C14—O3	−7.14 (11)
C1—C6—C7—C8	−121.77 (9)	C12—C13—C14—O3	179.52 (8)
C5—C6—C7—C8	61.73 (11)	O2—C13—C14—C15	170.62 (8)
O4—C7—C8—C9	−162.01 (9)	C12—C13—C14—C15	−2.72 (13)
C6—C7—C8—C9	19.86 (12)	O3—C14—C15—C10	−179.90 (8)
C7—C8—C9—C10	174.62 (8)	C13—C14—C15—C10	2.57 (13)
C8—C9—C10—C15	31.54 (13)	C11—C10—C15—C14	0.95 (13)
C8—C9—C10—C11	−145.86 (9)	C9—C10—C15—C14	−176.36 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O3i	0.93	2.53	3.3442 (11)	147
C17—H17A···Cg1ii	0.96	2.60	3.2965 (11)	130

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10—C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O3i	0.93	2.53	3.3442 (11)	147
C17—H17A⋯Cg1ii	0.96	2.60	3.2965 (11)	130

Symmetry codes: (i) ; (ii) .