(E)-3-(3-Chloro-phen-yl)-1-(4-methoxy-phen-yl)prop-2-en-1-one.

The title mol-ecule, C(16)H(13)ClO(2), is trans with respect to the C=C double bond. The dihedral angles between the mean plane of the prop-2-en-1-one unit and those of the 3-chloro- and 4-meth-oxy-substituted benzene rings are 20.93 (9) and 20.42 (10)°, respectively, and the dihedral angle between the mean planes of the two benzene rings is 40.96 (5)°. The crystal structure is stabilized by weak inter-molecular C-H⋯O hydrogen bonds, forming chains along the b axis.

Related literature

For the biological activity of chalcones, see: Dimmock et al. (1999 ▶); Opletalova & Sedivy (1999 ▶); Lin et al. (2002 ▶); Nowakowska (2007 ▶). For the synthesis and biological activity of related chalcone derivatives, see: Hussain et al. (2009 ▶). For non-linear optical studies of chalcones, see: Sarojini et al. (2006 ▶); Poornesh et al. (2009 ▶); Shettigar et al. (2006 ▶; 2008 ▶). For related structures, see: Rosli et al. (2006 ▶); Patil et al. (2006 ▶); Harrison et al. (2006 ▶); Fun et al. (2008 ▶); Jasinski et al. (2010 ▶).

Experimental

Crystal data

C16H13ClO2

M = 272.71

Monoclinic,

a = 10.3415 (6) Å

b = 3.8938 (1) Å

c = 16.9152 (10) Å

β = 107.582 (2)°

V = 649.32 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.29 mm−1

T = 173 K

0.18 × 0.16 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.950, T max = 0.989

2099 measured reflections

2099 independent reflections

2075 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.073

S = 1.15

2099 reflections

173 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.14 e Å−3

Absolute structure: Flack (1983 ▶), 687 Friedel pairs

Flack parameter: 0.08 (6)

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017150/lh5044sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017150/lh5044Isup2.hkl

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

C16H13ClO2	F(000) = 284
Mr = 272.71	Dx = 1.395 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1186 reflections
a = 10.3415 (6) Å	θ = 1.0–27.5°
b = 3.8938 (1) Å	µ = 0.29 mm−1
c = 16.9152 (10) Å	T = 173 K
β = 107.582 (2)°	Plate, colourless
V = 649.32 (6) Å3	0.18 × 0.16 × 0.04 mm
Z = 2

Nonius KappaCCD diffractometer	2099 independent reflections
Radiation source: fine-focus sealed tube	2075 reflections with I > 2σ(I)
graphite	Rint = 0.000
ω and φ scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −12→12
Tmin = 0.950, Tmax = 0.989	k = −4→4
2099 measured reflections	l = −20→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026	H-atom parameters constrained
wR(F2) = 0.073	w = 1/[σ2(Fo2) + (0.0313P)2 + 0.151P] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max < 0.001
2099 reflections	Δρmax = 0.13 e Å−3
173 parameters	Δρmin = −0.14 e Å−3
1 restraint	Absolute structure: Flack (1983), 687 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.08 (6)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.28612 (5)	0.84356 (13)	−0.07337 (2)	0.03991 (15)
O1	1.26882 (11)	0.5880 (4)	0.35589 (7)	0.0330 (3)
O2	0.67938 (12)	0.6392 (4)	0.39544 (8)	0.0413 (4)
C1	0.85889 (16)	0.6328 (4)	0.33613 (10)	0.0247 (4)
C2	0.90929 (17)	0.7521 (4)	0.27311 (10)	0.0267 (4)
H2	0.8490	0.8486	0.2242	0.032*
C3	1.04622 (18)	0.7304 (5)	0.28148 (10)	0.0290 (4)
H3	1.0797	0.8125	0.2385	0.035*
C4	1.13507 (16)	0.5884 (4)	0.35290 (10)	0.0253 (4)
C5	1.08649 (17)	0.4606 (5)	0.41555 (10)	0.0264 (4)
H5	1.1465	0.3585	0.4637	0.032*
C6	0.94934 (17)	0.4851 (5)	0.40622 (10)	0.0261 (4)
H6	0.9158	0.3989	0.4488	0.031*
C7	1.36446 (17)	0.4448 (5)	0.42797 (12)	0.0365 (5)
H7A	1.4561	0.4645	0.4229	0.044*
H7B	1.3430	0.2022	0.4330	0.044*
H7C	1.3598	0.5697	0.4773	0.044*
C8	0.71475 (17)	0.6756 (5)	0.33309 (10)	0.0287 (4)
C9	0.61392 (17)	0.7636 (5)	0.25241 (10)	0.0284 (4)
H9	0.6357	0.7207	0.2026	0.034*
C10	0.49465 (16)	0.9000 (5)	0.24782 (10)	0.0276 (4)
H10	0.4780	0.9468	0.2990	0.033*
C11	0.38516 (17)	0.9868 (5)	0.17214 (11)	0.0252 (3)
C12	0.38969 (16)	0.8919 (5)	0.09297 (10)	0.0267 (4)
H12	0.4662	0.7735	0.0865	0.032*
C13	0.28167 (17)	0.9727 (5)	0.02468 (10)	0.0280 (4)
C14	0.16803 (17)	1.1442 (5)	0.03152 (11)	0.0311 (4)
H14	0.0946	1.1960	−0.0164	0.037*
C15	0.16385 (18)	1.2383 (5)	0.10952 (12)	0.0325 (4)
H15	0.0870	1.3567	0.1154	0.039*
C16	0.27161 (17)	1.1606 (5)	0.17948 (11)	0.0290 (4)
H16	0.2677	1.2268	0.2328	0.035*

	U11	U22	U33	U12	U13	U23
Cl1	0.0526 (3)	0.0409 (3)	0.0234 (2)	−0.0034 (2)	0.00716 (18)	0.0004 (2)
O1	0.0243 (6)	0.0444 (8)	0.0294 (6)	0.0004 (6)	0.0068 (5)	0.0020 (6)
O2	0.0302 (6)	0.0675 (10)	0.0268 (6)	0.0045 (7)	0.0093 (5)	0.0055 (7)
C1	0.0258 (8)	0.0247 (8)	0.0214 (8)	−0.0002 (7)	0.0037 (6)	−0.0034 (7)
C2	0.0300 (9)	0.0279 (9)	0.0201 (8)	0.0004 (7)	0.0044 (6)	0.0020 (7)
C3	0.0323 (8)	0.0330 (9)	0.0217 (8)	−0.0033 (7)	0.0082 (6)	−0.0001 (7)
C4	0.0255 (8)	0.0254 (8)	0.0242 (8)	−0.0018 (7)	0.0061 (6)	−0.0042 (7)
C5	0.0280 (8)	0.0268 (8)	0.0216 (8)	0.0014 (7)	0.0034 (6)	−0.0002 (7)
C6	0.0313 (8)	0.0264 (8)	0.0207 (8)	−0.0007 (7)	0.0080 (6)	−0.0009 (7)
C7	0.0260 (8)	0.0436 (12)	0.0349 (10)	0.0017 (8)	0.0017 (7)	0.0037 (9)
C8	0.0284 (8)	0.0325 (9)	0.0235 (8)	−0.0005 (8)	0.0055 (7)	−0.0017 (8)
C9	0.0262 (8)	0.0349 (10)	0.0227 (8)	−0.0006 (7)	0.0053 (6)	−0.0029 (8)
C10	0.0294 (8)	0.0307 (10)	0.0222 (8)	−0.0002 (8)	0.0071 (6)	0.0001 (7)
C11	0.0244 (7)	0.0245 (8)	0.0263 (8)	−0.0041 (7)	0.0069 (6)	0.0010 (7)
C12	0.0259 (8)	0.0266 (9)	0.0270 (8)	−0.0022 (7)	0.0070 (6)	−0.0001 (8)
C13	0.0331 (9)	0.0246 (8)	0.0250 (8)	−0.0075 (7)	0.0067 (7)	0.0008 (7)
C14	0.0276 (8)	0.0280 (9)	0.0319 (9)	−0.0034 (8)	0.0003 (7)	0.0064 (8)
C15	0.0249 (8)	0.0292 (10)	0.0427 (10)	0.0014 (7)	0.0090 (7)	0.0026 (8)
C16	0.0284 (8)	0.0298 (9)	0.0291 (9)	−0.0014 (8)	0.0091 (7)	−0.0001 (8)

Cl1—C13	1.747 (2)	C7—H7C	0.9800
O1—C4	1.369 (2)	C8—C9	1.486 (2)
O1—C7	1.431 (2)	C9—C10	1.323 (2)
O2—C8	1.225 (2)	C9—H9	0.9500
C1—C6	1.393 (2)	C10—C11	1.470 (2)
C1—C2	1.400 (2)	C10—H10	0.9500
C1—C8	1.485 (2)	C11—C16	1.393 (2)
C2—C3	1.383 (2)	C11—C12	1.404 (2)
C2—H2	0.9500	C12—C13	1.379 (2)
C3—C4	1.393 (2)	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.387 (3)
C4—C5	1.395 (2)	C14—C15	1.383 (3)
C5—C6	1.382 (2)	C14—H14	0.9500
C5—H5	0.9500	C15—C16	1.392 (2)
C6—H6	0.9500	C15—H15	0.9500
C7—H7A	0.9800	C16—H16	0.9500
C7—H7B	0.9800
C4—O1—C7	117.56 (13)	O2—C8—C9	120.56 (15)
C6—C1—C2	118.44 (15)	C1—C8—C9	118.44 (14)
C6—C1—C8	118.99 (14)	C10—C9—C8	121.97 (15)
C2—C1—C8	122.48 (14)	C10—C9—H9	119.0
C3—C2—C1	120.48 (15)	C8—C9—H9	119.0
C3—C2—H2	119.8	C9—C10—C11	127.06 (15)
C1—C2—H2	119.8	C9—C10—H10	116.5
C2—C3—C4	120.00 (15)	C11—C10—H10	116.5
C2—C3—H3	120.0	C16—C11—C12	119.01 (16)
C4—C3—H3	120.0	C16—C11—C10	118.85 (15)
O1—C4—C3	115.28 (14)	C12—C11—C10	122.11 (15)
O1—C4—C5	124.30 (15)	C13—C12—C11	119.15 (16)
C3—C4—C5	120.42 (15)	C13—C12—H12	120.4
C6—C5—C4	118.77 (15)	C11—C12—H12	120.4
C6—C5—H5	120.6	C12—C13—C14	122.17 (16)
C4—C5—H5	120.6	C12—C13—Cl1	118.86 (14)
C5—C6—C1	121.85 (15)	C14—C13—Cl1	118.94 (13)
C5—C6—H6	119.1	C15—C14—C13	118.62 (15)
C1—C6—H6	119.1	C15—C14—H14	120.7
O1—C7—H7A	109.5	C13—C14—H14	120.7
O1—C7—H7B	109.5	C14—C15—C16	120.40 (16)
H7A—C7—H7B	109.5	C14—C15—H15	119.8
O1—C7—H7C	109.5	C16—C15—H15	119.8
H7A—C7—H7C	109.5	C15—C16—C11	120.65 (16)
H7B—C7—H7C	109.5	C15—C16—H16	119.7
O2—C8—C1	120.99 (15)	C11—C16—H16	119.7
C6—C1—C2—C3	−1.5 (3)	O2—C8—C9—C10	19.7 (3)
C8—C1—C2—C3	174.97 (16)	C1—C8—C9—C10	−160.40 (17)
C1—C2—C3—C4	0.2 (3)	C8—C9—C10—C11	−177.75 (17)
C7—O1—C4—C3	−179.98 (16)	C9—C10—C11—C16	−173.68 (18)
C7—O1—C4—C5	0.4 (2)	C9—C10—C11—C12	8.1 (3)
C2—C3—C4—O1	−178.27 (15)	C16—C11—C12—C13	−0.1 (3)
C2—C3—C4—C5	1.4 (3)	C10—C11—C12—C13	178.09 (16)
O1—C4—C5—C6	178.08 (17)	C11—C12—C13—C14	−0.2 (3)
C3—C4—C5—C6	−1.5 (2)	C11—C12—C13—Cl1	−178.31 (13)
C4—C5—C6—C1	0.2 (3)	C12—C13—C14—C15	0.4 (3)
C2—C1—C6—C5	1.4 (3)	Cl1—C13—C14—C15	178.47 (14)
C8—C1—C6—C5	−175.25 (16)	C13—C14—C15—C16	−0.2 (3)
C6—C1—C8—O2	12.6 (3)	C14—C15—C16—C11	−0.1 (3)
C2—C1—C8—O2	−163.87 (19)	C12—C11—C16—C15	0.2 (3)
C6—C1—C8—C9	−167.35 (17)	C10—C11—C16—C15	−178.02 (16)
C2—C1—C8—C9	16.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O2i	0.98	2.58	3.545 (2)	168
C16—H16···O1ii	0.95	2.51	3.424 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O2i	0.98	2.58	3.545 (2)	168
C16—H16⋯O1ii	0.95	2.51	3.424 (2)	162

Symmetry codes: (i) ; (ii) .