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

In the title compound, C(15)H(11)ClO, the dihedral angle between the mean planes of the benzene ring and the chloro-substituted benzene ring is 48.8 (3)°. The dihedral angles between the mean plane of the prop-2-ene-1-one group and the mean planes of the 3-chloro-phenyl and benzene rings are 27.0 (4) and 27.9 (3)°, respectively. In the crystal, weak inter-molecular C-H⋯π-ring inter-actions occur.

Related literature

For background to chalcones, see: Chen et al. (1994 ▶); Marais et al. (2005 ▶); Poornesh et al. (2009 ▶); Ram et al. (2000 ▶); Sarojini et al. (2006 ▶); Shettigar et al. (2006 ▶, 2008 ▶); Troeberg et al. (2000 ▶). For related structures, see: Jasinski et al. (2007 ▶); Li & Su (1994 ▶).

Experimental

Crystal data

C15H11ClO

M = 242.69

Triclinic,

a = 5.8388 (7) Å

b = 7.5975 (11) Å

c = 13.1300 (16) Å

α = 83.182 (11)°

β = 89.422 (10)°

γ = 86.662 (11)°

V = 577.35 (13) Å3

Z = 2

Cu Kα radiation

μ = 2.74 mm−1

T = 110 K

0.50 × 0.32 × 0.28 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.541, T max = 1.000

3661 measured reflections

2243 independent reflections

2148 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.099

S = 1.02

2243 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97) (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809053458/tk2596sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053458/tk2596Isup2.hkl

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

C15H11ClO	Z = 2
Mr = 242.69	F(000) = 252
Triclinic, P1	Dx = 1.396 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 5.8388 (7) Å	Cell parameters from 3077 reflections
b = 7.5975 (11) Å	θ = 5.9–73.8°
c = 13.1300 (16) Å	µ = 2.74 mm−1
α = 83.182 (11)°	T = 110 K
β = 89.422 (10)°	Prism, colorless
γ = 86.662 (11)°	0.50 × 0.32 × 0.28 mm
V = 577.35 (13) Å3

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector	2243 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2148 reflections with I > 2σ(I)
graphite	Rint = 0.017
Detector resolution: 10.5081 pixels mm-1	θmax = 73.8°, θmin = 5.9°
ω scans	h = −7→5
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −9→9
Tmin = 0.541, Tmax = 1.000	l = −16→15
3661 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0647P)2 + 0.2987P] where P = (Fo2 + 2Fc2)/3
2243 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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
Cl	0.32652 (6)	0.68985 (5)	0.56518 (3)	0.02296 (15)
O	0.27901 (18)	0.72419 (15)	0.96930 (8)	0.0224 (3)
C1	0.5736 (2)	0.67070 (18)	0.84979 (11)	0.0160 (3)
C2	0.4270 (2)	0.69988 (18)	0.76536 (11)	0.0162 (3)
H2A	0.2759	0.7510	0.7719	0.019*
C3	0.5060 (3)	0.65289 (19)	0.67198 (11)	0.0165 (3)
C4	0.7258 (3)	0.57602 (19)	0.66031 (12)	0.0189 (3)
H4A	0.7771	0.5448	0.5956	0.023*
C5	0.8677 (3)	0.54612 (19)	0.74507 (12)	0.0193 (3)
H5A	1.0170	0.4916	0.7387	0.023*
C6	0.7950 (2)	0.59463 (19)	0.83940 (12)	0.0177 (3)
H6A	0.8955	0.5762	0.8966	0.021*
C7	0.4848 (3)	0.72066 (19)	0.95085 (11)	0.0175 (3)
C8	0.6548 (3)	0.7663 (2)	1.02521 (12)	0.0192 (3)
H8A	0.8081	0.7850	1.0035	0.023*
C9	0.5952 (2)	0.78129 (19)	1.12239 (11)	0.0170 (3)
H9A	0.4423	0.7560	1.1418	0.020*
C10	0.7434 (2)	0.83314 (19)	1.20198 (11)	0.0161 (3)
C11	0.9534 (3)	0.90987 (19)	1.17865 (11)	0.0180 (3)
H11A	1.0036	0.9293	1.1094	0.022*
C12	1.0875 (3)	0.95730 (19)	1.25607 (12)	0.0194 (3)
H12A	1.2287	1.0103	1.2396	0.023*
C13	1.0172 (3)	0.9280 (2)	1.35792 (12)	0.0217 (3)
H13A	1.1107	0.9600	1.4108	0.026*
C14	0.8103 (3)	0.8519 (2)	1.38218 (12)	0.0221 (3)
H14A	0.7623	0.8313	1.4517	0.026*
C15	0.6734 (3)	0.80576 (19)	1.30478 (12)	0.0185 (3)
H15A	0.5309	0.7552	1.3217	0.022*

	U11	U22	U33	U12	U13	U23
Cl	0.0222 (2)	0.0308 (2)	0.0164 (2)	0.00195 (15)	−0.00390 (14)	−0.00610 (14)
O	0.0149 (5)	0.0340 (6)	0.0190 (5)	−0.0032 (4)	0.0000 (4)	−0.0044 (4)
C1	0.0171 (7)	0.0139 (6)	0.0173 (7)	−0.0054 (5)	0.0001 (5)	−0.0010 (5)
C2	0.0140 (7)	0.0149 (7)	0.0198 (7)	−0.0028 (5)	0.0000 (5)	−0.0019 (5)
C3	0.0177 (7)	0.0173 (7)	0.0152 (7)	−0.0036 (5)	−0.0023 (5)	−0.0031 (5)
C4	0.0209 (7)	0.0165 (7)	0.0203 (7)	−0.0034 (5)	0.0034 (6)	−0.0050 (6)
C5	0.0145 (7)	0.0156 (7)	0.0277 (8)	−0.0003 (5)	0.0009 (6)	−0.0030 (6)
C6	0.0161 (7)	0.0160 (7)	0.0208 (7)	−0.0032 (5)	−0.0023 (5)	−0.0001 (5)
C7	0.0175 (7)	0.0168 (7)	0.0179 (7)	−0.0030 (5)	−0.0005 (5)	−0.0002 (5)
C8	0.0166 (7)	0.0213 (7)	0.0199 (7)	−0.0033 (6)	−0.0009 (6)	−0.0023 (6)
C9	0.0143 (7)	0.0154 (7)	0.0212 (7)	−0.0003 (5)	−0.0004 (5)	−0.0021 (5)
C10	0.0155 (7)	0.0139 (6)	0.0188 (7)	0.0015 (5)	−0.0010 (5)	−0.0030 (5)
C11	0.0173 (7)	0.0175 (7)	0.0189 (7)	−0.0001 (5)	0.0011 (5)	−0.0024 (5)
C12	0.0161 (7)	0.0156 (7)	0.0264 (8)	−0.0011 (5)	−0.0017 (6)	−0.0020 (6)
C13	0.0228 (8)	0.0201 (7)	0.0227 (8)	0.0003 (6)	−0.0064 (6)	−0.0046 (6)
C14	0.0268 (8)	0.0221 (8)	0.0171 (7)	0.0001 (6)	0.0010 (6)	−0.0027 (6)
C15	0.0172 (7)	0.0166 (7)	0.0220 (8)	−0.0010 (5)	0.0029 (6)	−0.0032 (6)

Cl—C3	1.7452 (15)	C8—H8A	0.9500
O—C7	1.2226 (19)	C9—C10	1.467 (2)
C1—C2	1.396 (2)	C9—H9A	0.9500
C1—C6	1.397 (2)	C10—C15	1.402 (2)
C1—C7	1.502 (2)	C10—C11	1.404 (2)
C2—C3	1.385 (2)	C11—C12	1.383 (2)
C2—H2A	0.9500	C11—H11A	0.9500
C3—C4	1.393 (2)	C12—C13	1.391 (2)
C4—C5	1.383 (2)	C12—H12A	0.9500
C4—H4A	0.9500	C13—C14	1.387 (2)
C5—C6	1.389 (2)	C13—H13A	0.9500
C5—H5A	0.9500	C14—C15	1.389 (2)
C6—H6A	0.9500	C14—H14A	0.9500
C7—C8	1.483 (2)	C15—H15A	0.9500
C8—C9	1.335 (2)
C2—C1—C6	120.12 (14)	C7—C8—H8A	119.6
C2—C1—C7	118.15 (13)	C8—C9—C10	126.15 (14)
C6—C1—C7	121.73 (13)	C8—C9—H9A	116.9
C3—C2—C1	118.72 (13)	C10—C9—H9A	116.9
C3—C2—H2A	120.6	C15—C10—C11	118.75 (13)
C1—C2—H2A	120.6	C15—C10—C9	119.08 (13)
C2—C3—C4	121.96 (13)	C11—C10—C9	122.18 (13)
C2—C3—Cl	119.50 (11)	C12—C11—C10	120.27 (14)
C4—C3—Cl	118.54 (11)	C12—C11—H11A	119.9
C5—C4—C3	118.53 (14)	C10—C11—H11A	119.9
C5—C4—H4A	120.7	C11—C12—C13	120.46 (14)
C3—C4—H4A	120.7	C11—C12—H12A	119.8
C4—C5—C6	120.91 (14)	C13—C12—H12A	119.8
C4—C5—H5A	119.5	C14—C13—C12	119.92 (14)
C6—C5—H5A	119.5	C14—C13—H13A	120.0
C5—C6—C1	119.74 (14)	C12—C13—H13A	120.0
C5—C6—H6A	120.1	C13—C14—C15	119.97 (14)
C1—C6—H6A	120.1	C13—C14—H14A	120.0
O—C7—C8	122.19 (14)	C15—C14—H14A	120.0
O—C7—C1	120.25 (13)	C14—C15—C10	120.63 (14)
C8—C7—C1	117.56 (13)	C14—C15—H15A	119.7
C9—C8—C7	120.80 (14)	C10—C15—H15A	119.7
C9—C8—H8A	119.6
C6—C1—C2—C3	−0.3 (2)	O—C7—C8—C9	12.5 (2)
C7—C1—C2—C3	−179.41 (12)	C1—C7—C8—C9	−168.11 (14)
C1—C2—C3—C4	0.7 (2)	C7—C8—C9—C10	−177.12 (13)
C1—C2—C3—Cl	−179.48 (10)	C8—C9—C10—C15	−166.17 (15)
C2—C3—C4—C5	0.1 (2)	C8—C9—C10—C11	14.0 (2)
Cl—C3—C4—C5	−179.76 (11)	C15—C10—C11—C12	0.0 (2)
C3—C4—C5—C6	−1.2 (2)	C9—C10—C11—C12	179.79 (13)
C4—C5—C6—C1	1.6 (2)	C10—C11—C12—C13	0.6 (2)
C2—C1—C6—C5	−0.8 (2)	C11—C12—C13—C14	−0.5 (2)
C7—C1—C6—C5	178.26 (12)	C12—C13—C14—C15	−0.2 (2)
C2—C1—C7—O	26.0 (2)	C13—C14—C15—C10	0.9 (2)
C6—C1—C7—O	−153.08 (14)	C11—C10—C15—C14	−0.7 (2)
C2—C1—C7—C8	−153.42 (13)	C9—C10—C15—C14	179.46 (13)
C6—C1—C7—C8	27.50 (19)

Cg1 is the centroid of the C1–C6 ring and Cg2 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···Cg2i	0.95	2.90	3.5541 (16)	127
C5—H5A···Cg2ii	0.95	2.90	3.5338 (17)	125
C12—H12A···Cg1iii	0.95	2.92	3.6040 (17)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯Cg2i	0.95	2.90	3.5541 (16)	127
C5—H5A⋯Cg2ii	0.95	2.90	3.5338 (17)	125
C12—H12A⋯Cg1iii	0.95	2.92	3.6040 (17)	130

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C1–C6 ring and Cg2 is the centroid of the C10–C15 ring.