(E)-3-(2,6-Dichloro-phen-yl)-1-(4-methoxy-phen-yl)prop-2-en-1-one.

In the title compound, C(16)H(12)Cl(2)O(2), the dichloro-phenyl and methoxy-phenyl groups are linked by a prop-2-en-1-one group. The C=C double bond is trans configured. The mol-ecule is not planar, as can be seen from the dihedral angle of 6.21 (7)° between the planes of the two rings. The crystal structure can be described by two types of crossed layers which are parallel to (110) and (10).

Related literature

For background to the applications of chalcones, see: Liu et al. (2003 ▶); Li et al. (1995 ▶); Hsieh et al. (1998 ▶); Barford et al. (2002 ▶); Rojas et al. (2002 ▶); Nerya et al. (2006 ▶); Yang et al. (2000 ▶); Ducki et al. (1998 ▶); Goto et al. (1991 ▶); Indira et al. (2002 ▶); Lawrence et al. (2001 ▶); Nielsen et al. (2005 ▶); Sarker & Nahar (2004 ▶); Sarojini et al. (2006 ▶). For related structures, see: Yathirajan et al. (2007 ▶); Butcher et al. (2007 ▶); Fischer et al. (2007 ▶).

Experimental

Crystal data

C16H12Cl2O2

M = 307.16

Orthorhombic,

a = 6.4793 (2) Å

b = 12.9807 (5) Å

c = 16.7819 (8) Å

V = 1411.46 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.46 mm−1

T = 100 K

0.37 × 0.28 × 0.2 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS, Bruker, 1998 ▶) T min = 0.824, T max = 0.913

6643 measured reflections

3211 independent reflections

2964 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.090

S = 1.05

3211 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 1331 Friedel pairs

Flack parameter: 0.01 (6)

Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020145/bq2141sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020145/bq2141Isup2.hkl

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

C16H12Cl2O2	F(000) = 632
Mr = 307.16	Dx = 1.445 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3041 reflections
a = 6.4793 (2) Å	θ = 2.4–27.4°
b = 12.9807 (5) Å	µ = 0.46 mm−1
c = 16.7819 (8) Å	T = 100 K
V = 1411.46 (10) Å3	Prism, colourless
Z = 4	0.37 × 0.28 × 0.2 mm

Bruker APEXII diffractometer	2964 reflections with I > 2σ(I)
graphite	Rint = 0.029
CCD rotation images, thin slices scans	θmax = 27.4°, θmin = 3.5°
Absorption correction: multi-scan (SADABS, Bruker, 1998)	h = −6→8
Tmin = 0.824, Tmax = 0.913	k = −15→16
6643 measured reflections	l = −20→21
3211 independent reflections

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0409P)2 + 0.5074P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.002
3211 reflections	Δρmax = 0.51 e Å−3
182 parameters	Δρmin = −0.20 e Å−3
0 restraints	Absolute structure: Flack (1983), 1331 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (6)

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	0.49869 (7)	1.03293 (4)	0.58897 (3)	0.02481 (12)
Cl5	0.06450 (7)	0.84015 (4)	0.35072 (3)	0.02267 (12)
C1	0.2990 (3)	0.95544 (14)	0.55269 (13)	0.0174 (4)
C2	0.1599 (3)	0.91924 (15)	0.60937 (13)	0.0211 (4)
H2	0.1779	0.9363	0.664	0.025*
C3	−0.0051 (3)	0.85821 (14)	0.58604 (13)	0.0226 (4)
H3	−0.1001	0.8333	0.6246	0.027*
C4	−0.0312 (3)	0.83360 (14)	0.50613 (12)	0.0206 (4)
H4	−0.1422	0.7907	0.4898	0.025*
C5	0.1068 (3)	0.87235 (14)	0.45044 (12)	0.0167 (4)
C6	0.2774 (3)	0.93459 (13)	0.47063 (13)	0.0149 (4)
C7	0.4050 (3)	0.97926 (13)	0.40676 (12)	0.0150 (4)
H7	0.3354	0.9928	0.358	0.018*
C8	0.6062 (3)	1.00344 (13)	0.40815 (13)	0.0169 (4)
H8	0.6877	0.9871	0.4535	0.02*
C9	0.7012 (3)	1.05587 (14)	0.33855 (12)	0.0172 (4)
O10	0.61836 (19)	1.05435 (10)	0.27255 (9)	0.0215 (3)
C11	0.8991 (3)	1.11288 (13)	0.35089 (12)	0.0154 (4)
C12	0.9741 (3)	1.13891 (13)	0.42704 (11)	0.0164 (4)
H12	0.9017	1.1168	0.4732	0.02*
C13	1.1527 (3)	1.19652 (14)	0.43510 (12)	0.0172 (4)
H13	1.2022	1.2139	0.4867	0.021*
C14	1.0073 (3)	1.14718 (13)	0.28402 (11)	0.0170 (4)
H14	0.9569	1.131	0.2324	0.02*
C15	1.1874 (3)	1.20463 (14)	0.29156 (12)	0.0173 (4)
H15	1.26	1.227	0.2455	0.021*
C16	1.2603 (3)	1.22906 (14)	0.36746 (12)	0.0172 (4)
O17	1.4376 (2)	1.28344 (10)	0.38116 (8)	0.0224 (3)
C18	1.5488 (3)	1.32052 (14)	0.31247 (13)	0.0225 (4)
H18A	1.5785	1.2628	0.2766	0.034*
H18B	1.6786	1.3522	0.3297	0.034*
H18C	1.4648	1.3718	0.2844	0.034*

	U11	U22	U33	U12	U13	U23
Cl1	0.0219 (2)	0.0314 (2)	0.0211 (3)	−0.0074 (2)	−0.0005 (2)	−0.0049 (2)
Cl5	0.0219 (2)	0.0227 (2)	0.0234 (3)	−0.0029 (2)	−0.0021 (2)	−0.0059 (2)
C1	0.0151 (8)	0.0157 (9)	0.0215 (11)	0.0023 (8)	−0.0002 (8)	0.0001 (8)
C2	0.0214 (10)	0.0226 (10)	0.0193 (11)	0.0027 (9)	0.0009 (8)	0.0047 (8)
C3	0.0193 (9)	0.0232 (9)	0.0255 (11)	−0.0005 (9)	0.0070 (9)	0.0083 (8)
C4	0.0156 (9)	0.0156 (8)	0.0305 (12)	−0.0028 (8)	0.0000 (8)	0.0023 (8)
C5	0.0157 (9)	0.0123 (8)	0.0221 (11)	0.0024 (8)	−0.0027 (8)	0.0005 (7)
C6	0.0129 (8)	0.0116 (8)	0.0203 (10)	0.0030 (7)	0.0014 (7)	0.0009 (7)
C7	0.0188 (9)	0.0112 (8)	0.0150 (10)	0.0024 (7)	−0.0008 (8)	0.0005 (8)
C8	0.0163 (9)	0.0161 (9)	0.0182 (11)	0.0025 (7)	−0.0013 (8)	0.0034 (8)
C9	0.0160 (8)	0.0161 (9)	0.0195 (11)	0.0034 (7)	0.0020 (8)	−0.0002 (8)
O10	0.0188 (6)	0.0280 (7)	0.0176 (8)	−0.0035 (6)	−0.0014 (6)	0.0022 (6)
C11	0.0140 (8)	0.0150 (8)	0.0172 (10)	0.0021 (7)	0.0000 (8)	0.0005 (8)
C12	0.0180 (9)	0.0168 (9)	0.0146 (10)	0.0039 (8)	0.0026 (7)	0.0019 (7)
C13	0.0212 (9)	0.0170 (9)	0.0135 (10)	0.0022 (8)	−0.0034 (8)	−0.0031 (7)
C14	0.0169 (8)	0.0193 (9)	0.0149 (9)	0.0017 (9)	−0.0016 (8)	0.0009 (7)
C15	0.0170 (9)	0.0185 (9)	0.0163 (10)	0.0003 (8)	0.0022 (8)	0.0040 (8)
C16	0.0166 (9)	0.0121 (8)	0.0228 (12)	0.0005 (8)	−0.0013 (7)	0.0013 (8)
O17	0.0214 (7)	0.0264 (7)	0.0195 (8)	−0.0088 (6)	−0.0016 (6)	0.0005 (6)
C18	0.0202 (10)	0.0218 (9)	0.0256 (11)	−0.0072 (8)	0.0001 (8)	0.0037 (8)

Cl1—C1	1.7484 (19)	C9—C11	1.494 (3)
Cl5—C5	1.747 (2)	C11—C14	1.396 (3)
C1—C2	1.392 (3)	C11—C12	1.409 (3)
C1—C6	1.410 (3)	C12—C13	1.384 (3)
C2—C3	1.387 (3)	C12—H12	0.95
C2—H2	0.95	C13—C16	1.397 (3)
C3—C4	1.389 (3)	C13—H13	0.95
C3—H3	0.95	C14—C15	1.391 (3)
C4—C5	1.388 (3)	C14—H14	0.95
C4—H4	0.95	C15—C16	1.395 (3)
C5—C6	1.410 (3)	C15—H15	0.95
C6—C7	1.473 (3)	C16—O17	1.368 (2)
C7—C8	1.342 (2)	O17—C18	1.442 (2)
C7—H7	0.95	C18—H18A	0.98
C8—C9	1.485 (3)	C18—H18B	0.98
C8—H8	0.95	C18—H18C	0.98
C9—O10	1.231 (2)
C2—C1—C6	122.56 (18)	C8—C9—C11	118.26 (17)
C2—C1—Cl1	115.81 (16)	C14—C11—C12	118.64 (16)
C6—C1—Cl1	121.59 (15)	C14—C11—C9	118.51 (18)
C3—C2—C1	119.9 (2)	C12—C11—C9	122.73 (17)
C3—C2—H2	120	C13—C12—C11	120.46 (17)
C1—C2—H2	120	C13—C12—H12	119.8
C2—C3—C4	119.84 (18)	C11—C12—H12	119.8
C2—C3—H3	120.1	C12—C13—C16	120.05 (18)
C4—C3—H3	120.1	C12—C13—H13	120
C5—C4—C3	119.26 (17)	C16—C13—H13	120
C5—C4—H4	120.4	C15—C14—C11	121.28 (18)
C3—C4—H4	120.4	C15—C14—H14	119.4
C4—C5—C6	123.41 (19)	C11—C14—H14	119.4
C4—C5—Cl5	117.23 (14)	C14—C15—C16	119.28 (18)
C6—C5—Cl5	119.36 (15)	C14—C15—H15	120.4
C1—C6—C5	114.98 (18)	C16—C15—H15	120.4
C1—C6—C7	125.42 (17)	O17—C16—C15	123.72 (18)
C5—C6—C7	119.37 (18)	O17—C16—C13	116.00 (18)
C8—C7—C6	128.68 (19)	C15—C16—C13	120.27 (17)
C8—C7—H7	115.7	C16—O17—C18	117.23 (15)
C6—C7—H7	115.7	O17—C18—H18A	109.5
C7—C8—C9	119.76 (19)	O17—C18—H18B	109.5
C7—C8—H8	120.1	H18A—C18—H18B	109.5
C9—C8—H8	120.1	O17—C18—H18C	109.5
O10—C9—C8	121.29 (17)	H18A—C18—H18C	109.5
O10—C9—C11	120.44 (17)	H18B—C18—H18C	109.5
C6—C1—C2—C3	1.5 (3)	C7—C8—C9—C11	159.67 (16)
Cl1—C1—C2—C3	179.21 (14)	O10—C9—C11—C14	−12.1 (3)
C1—C2—C3—C4	−0.1 (3)	C8—C9—C11—C14	169.21 (16)
C2—C3—C4—C5	−1.3 (3)	O10—C9—C11—C12	163.91 (17)
C3—C4—C5—C6	1.4 (3)	C8—C9—C11—C12	−14.8 (2)
C3—C4—C5—Cl5	−179.22 (14)	C14—C11—C12—C13	−0.6 (2)
C2—C1—C6—C5	−1.4 (3)	C9—C11—C12—C13	−176.57 (16)
Cl1—C1—C6—C5	−178.94 (13)	C11—C12—C13—C16	−0.2 (3)
C2—C1—C6—C7	173.05 (17)	C12—C11—C14—C15	1.0 (2)
Cl1—C1—C6—C7	−4.5 (3)	C9—C11—C14—C15	177.10 (16)
C4—C5—C6—C1	−0.1 (2)	C11—C14—C15—C16	−0.5 (3)
Cl5—C5—C6—C1	−179.47 (13)	C14—C15—C16—O17	178.75 (16)
C4—C5—C6—C7	−174.87 (16)	C14—C15—C16—C13	−0.3 (3)
Cl5—C5—C6—C7	5.8 (2)	C12—C13—C16—O17	−178.48 (15)
C1—C6—C7—C8	35.1 (3)	C12—C13—C16—C15	0.6 (3)
C5—C6—C7—C8	−150.75 (19)	C15—C16—O17—C18	2.6 (2)
C6—C7—C8—C9	−175.13 (17)	C13—C16—O17—C18	−178.31 (16)
C7—C8—C9—O10	−19.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cg1i	0.95	2.84	3.727	157
C7—H7···Cg2i	0.95	2.85	3.360	115

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cg1i	0.95	2.84	3.727	157
C7—H7⋯Cg2i	0.95	2.85	3.360	115

Symmetry code: (i) . Cg1 and Cg2 are the centroids of the C1–C6 and C11–C16 rings, respectively.