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

The title compound, C(16)H(13)ClO(2), adopts an E configuration with respect to the double bond of the propenone unit. The two benzene rings are twisted slightly from each other, making a dihedral angle of 7.14 (5)°. The mol-ecules are arranged in stacks, in which adjacent mol-ecules are related by inversion symmetry and form π-π inter-actions with a centroid-centroid distance of 3.7098 (6) Å. C-H⋯O and C-H⋯π inter-actions are formed between neighbouring mol-ecules.

Related literature

For related literature, see: Chantrapromma et al. (2005 ▶, 2006 ▶); Fun et al. (2006 ▶); Patil, Fun et al. (2007 ▶); Patil, Dharmaprakash et al. (2006 ▶, 2007 ▶).

Experimental

Crystal data

C16H13ClO2

M = 272.71

Triclinic,

a = 7.7352 (2) Å

b = 8.1405 (2) Å

c = 10.7411 (2) Å

α = 87.392 (1)°

β = 82.147 (1)°

γ = 74.794 (1)°

V = 646.52 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.29 mm−1

T = 100.0 (1) K

0.38 × 0.30 × 0.16 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.899, T max = 0.955

17497 measured reflections

4314 independent reflections

3644 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.101

S = 1.06

4314 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808021910/bi2296sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021910/bi2296Isup2.hkl

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

C16H13ClO2	Z = 2
Mr = 272.71	F000 = 284
Triclinic, P1	Dx = 1.401 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.7352 (2) Å	Cell parameters from 7792 reflections
b = 8.1405 (2) Å	θ = 2.2–37.5º
c = 10.7411 (2) Å	µ = 0.29 mm−1
α = 87.392 (1)º	T = 100.0 (1) K
β = 82.147 (1)º	Block, colourless
γ = 74.794 (1)º	0.38 × 0.30 × 0.16 mm
V = 646.52 (3) Å3

Bruker SMART APEXII CCD diffractometer	4314 independent reflections
Radiation source: fine-focus sealed tube	3644 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.025
T = 100(1) K	θmax = 31.7º
φ and ω scans	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −11→10
Tmin = 0.899, Tmax = 0.955	k = −11→12
17497 measured reflections	l = −15→15

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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0513P)2 + 0.1689P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
4314 reflections	Δρmax = 0.53 e Å−3
173 parameters	Δρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	1.15204 (4)	0.08594 (3)	−0.41471 (2)	0.02216 (8)
O1	0.78728 (11)	0.44819 (10)	−0.05788 (8)	0.02200 (17)
O2	0.46589 (11)	0.70028 (11)	0.36344 (8)	0.02281 (17)
C1	1.29054 (14)	−0.01282 (13)	−0.30363 (10)	0.01529 (19)
C2	1.44112 (15)	−0.14294 (13)	−0.34590 (10)	0.0184 (2)
H2A	1.4678	−0.1705	−0.4307	0.022*
C3	1.55059 (15)	−0.23075 (13)	−0.25988 (11)	0.0196 (2)
H3A	1.6517	−0.3178	−0.2870	0.024*
C4	1.51011 (15)	−0.18945 (13)	−0.13323 (11)	0.0189 (2)
H4A	1.5830	−0.2495	−0.0755	0.023*
C5	1.36046 (14)	−0.05817 (13)	−0.09349 (10)	0.0172 (2)
H5A	1.3348	−0.0311	−0.0086	0.021*
C6	1.24650 (14)	0.03518 (12)	−0.17720 (10)	0.01485 (19)
C7	1.09255 (14)	0.17825 (13)	−0.13473 (10)	0.01589 (19)
H7A	1.0407	0.2526	−0.1957	0.019*
C8	1.02124 (15)	0.20974 (13)	−0.01471 (10)	0.0173 (2)
H8A	1.0667	0.1341	0.0477	0.021*
C9	0.87148 (14)	0.36241 (13)	0.02113 (10)	0.01643 (19)
C10	0.82784 (14)	0.40997 (13)	0.15679 (10)	0.01584 (19)
C11	0.94385 (16)	0.34122 (14)	0.24498 (11)	0.0207 (2)
H11A	1.0518	0.2604	0.2210	0.025*
C12	0.89719 (18)	0.39431 (15)	0.36938 (11)	0.0248 (2)
H12A	0.9748	0.3489	0.4284	0.030*
C13	0.73691 (17)	0.51359 (14)	0.40576 (11)	0.0218 (2)
H13A	0.7062	0.5474	0.4892	0.026*
C14	0.62110 (15)	0.58335 (13)	0.31749 (10)	0.0173 (2)
C15	0.66548 (14)	0.53249 (13)	0.19298 (10)	0.01602 (19)
H15A	0.5882	0.5793	0.1341	0.019*
C16	0.34703 (16)	0.78256 (16)	0.27587 (12)	0.0253 (2)
H16A	0.2445	0.8619	0.3194	0.038*
H16B	0.3070	0.6989	0.2355	0.038*
H16C	0.4096	0.8423	0.2137	0.038*

	U11	U22	U33	U12	U13	U23
Cl1	0.02040 (14)	0.02714 (14)	0.01654 (13)	−0.00027 (10)	−0.00537 (9)	−0.00122 (9)
O1	0.0219 (4)	0.0231 (4)	0.0173 (4)	0.0008 (3)	−0.0021 (3)	−0.0019 (3)
O2	0.0212 (4)	0.0263 (4)	0.0173 (4)	−0.0009 (3)	0.0018 (3)	−0.0059 (3)
C1	0.0140 (4)	0.0170 (4)	0.0154 (4)	−0.0045 (4)	−0.0027 (4)	−0.0004 (3)
C2	0.0166 (5)	0.0204 (5)	0.0177 (5)	−0.0041 (4)	−0.0005 (4)	−0.0049 (4)
C3	0.0155 (5)	0.0170 (4)	0.0249 (5)	−0.0014 (4)	−0.0019 (4)	−0.0049 (4)
C4	0.0168 (5)	0.0179 (5)	0.0223 (5)	−0.0030 (4)	−0.0061 (4)	−0.0004 (4)
C5	0.0162 (5)	0.0197 (5)	0.0159 (5)	−0.0044 (4)	−0.0027 (4)	−0.0019 (4)
C6	0.0129 (4)	0.0159 (4)	0.0162 (5)	−0.0043 (3)	−0.0014 (3)	−0.0022 (3)
C7	0.0137 (4)	0.0161 (4)	0.0181 (5)	−0.0038 (3)	−0.0019 (4)	−0.0023 (3)
C8	0.0173 (5)	0.0150 (4)	0.0184 (5)	−0.0029 (4)	0.0000 (4)	−0.0006 (4)
C9	0.0152 (5)	0.0162 (4)	0.0176 (5)	−0.0046 (4)	0.0005 (4)	−0.0023 (3)
C10	0.0168 (5)	0.0158 (4)	0.0154 (4)	−0.0056 (4)	−0.0005 (4)	−0.0015 (3)
C11	0.0201 (5)	0.0191 (5)	0.0218 (5)	−0.0019 (4)	−0.0042 (4)	−0.0028 (4)
C12	0.0303 (6)	0.0228 (5)	0.0204 (5)	−0.0022 (5)	−0.0100 (5)	−0.0007 (4)
C13	0.0286 (6)	0.0216 (5)	0.0151 (5)	−0.0058 (4)	−0.0025 (4)	−0.0027 (4)
C14	0.0185 (5)	0.0166 (4)	0.0168 (5)	−0.0058 (4)	0.0013 (4)	−0.0028 (4)
C15	0.0163 (5)	0.0172 (4)	0.0150 (5)	−0.0056 (4)	−0.0009 (4)	−0.0008 (3)
C16	0.0173 (5)	0.0288 (6)	0.0272 (6)	−0.0010 (4)	−0.0022 (4)	−0.0070 (5)

Cl1—C1	1.7400 (11)	C8—C9	1.4836 (15)
O1—C9	1.2208 (14)	C8—H8A	0.930
O2—C14	1.3684 (13)	C9—C10	1.4952 (14)
O2—C16	1.4264 (15)	C10—C11	1.3915 (15)
C1—C2	1.3917 (14)	C10—C15	1.4028 (14)
C1—C6	1.4018 (14)	C11—C12	1.3933 (16)
C2—C3	1.3849 (16)	C11—H11A	0.930
C2—H2A	0.930	C12—C13	1.3796 (17)
C3—C4	1.3899 (16)	C12—H12A	0.930
C3—H3A	0.930	C13—C14	1.3929 (16)
C4—C5	1.3863 (15)	C13—H13A	0.930
C4—H4A	0.930	C14—C15	1.3886 (14)
C5—C6	1.4021 (15)	C15—H15A	0.930
C5—H5A	0.930	C16—H16A	0.960
C6—C7	1.4680 (14)	C16—H16B	0.960
C7—C8	1.3391 (15)	C16—H16C	0.960
C7—H7A	0.930
C14—O2—C16	117.57 (9)	O1—C9—C10	120.76 (10)
C2—C1—C6	122.55 (10)	C8—C9—C10	118.14 (9)
C2—C1—Cl1	116.93 (8)	C11—C10—C15	120.12 (10)
C6—C1—Cl1	120.49 (8)	C11—C10—C9	122.44 (10)
C3—C2—C1	119.02 (10)	C15—C10—C9	117.41 (9)
C3—C2—H2A	120.5	C10—C11—C12	119.56 (10)
C1—C2—H2A	120.5	C10—C11—H11A	120.2
C2—C3—C4	120.35 (10)	C12—C11—H11A	120.2
C2—C3—H3A	119.8	C13—C12—C11	120.58 (11)
C4—C3—H3A	119.8	C13—C12—H12A	119.7
C5—C4—C3	119.61 (10)	C11—C12—H12A	119.7
C5—C4—H4A	120.2	C12—C13—C14	119.96 (10)
C3—C4—H4A	120.2	C12—C13—H13A	120.0
C4—C5—C6	122.09 (10)	C14—C13—H13A	120.0
C4—C5—H5A	119.0	O2—C14—C15	124.45 (10)
C6—C5—H5A	119.0	O2—C14—C13	115.23 (10)
C1—C6—C5	116.37 (9)	C15—C14—C13	120.32 (10)
C1—C6—C7	122.05 (9)	C14—C15—C10	119.46 (10)
C5—C6—C7	121.56 (9)	C14—C15—H15A	120.3
C8—C7—C6	124.89 (10)	C10—C15—H15A	120.3
C8—C7—H7A	117.6	O2—C16—H16A	109.5
C6—C7—H7A	117.6	O2—C16—H16B	109.5
C7—C8—C9	121.58 (10)	H16A—C16—H16B	109.5
C7—C8—H8A	119.2	O2—C16—H16C	109.5
C9—C8—H8A	119.2	H16A—C16—H16C	109.5
O1—C9—C8	121.09 (10)	H16B—C16—H16C	109.5
C6—C1—C2—C3	1.08 (15)	O1—C9—C10—C11	−164.94 (10)
Cl1—C1—C2—C3	−176.96 (8)	C8—C9—C10—C11	14.25 (15)
C1—C2—C3—C4	0.12 (16)	O1—C9—C10—C15	13.15 (15)
C2—C3—C4—C5	−0.79 (16)	C8—C9—C10—C15	−167.66 (9)
C3—C4—C5—C6	0.30 (16)	C15—C10—C11—C12	0.30 (16)
C2—C1—C6—C5	−1.52 (15)	C9—C10—C11—C12	178.33 (10)
Cl1—C1—C6—C5	176.45 (7)	C10—C11—C12—C13	0.30 (18)
C2—C1—C6—C7	176.86 (9)	C11—C12—C13—C14	−0.69 (18)
Cl1—C1—C6—C7	−5.17 (13)	C16—O2—C14—C15	−3.86 (15)
C4—C5—C6—C1	0.82 (15)	C16—O2—C14—C13	176.68 (10)
C4—C5—C6—C7	−177.57 (10)	C12—C13—C14—O2	179.96 (10)
C1—C6—C7—C8	165.91 (10)	C12—C13—C14—C15	0.48 (17)
C5—C6—C7—C8	−15.79 (15)	O2—C14—C15—C10	−179.32 (9)
C6—C7—C8—C9	176.74 (9)	C13—C14—C15—C10	0.11 (15)
C7—C8—C9—O1	12.94 (16)	C11—C10—C15—C14	−0.50 (15)
C7—C8—C9—C10	−166.25 (9)	C9—C10—C15—C14	−178.64 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2i	0.93	2.50	3.3887 (13)	161
C4—H4A···O1ii	0.93	2.57	3.3003 (13)	136
C16—H16B···O1iii	0.96	2.58	3.4899 (14)	158
C16—H16C···Cg1iv	0.96	2.82	3.6137 (14)	135

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O2i	0.93	2.50	3.3887 (13)	161
C4—H4A⋯O1ii	0.93	2.57	3.3003 (13)	136
C16—H16B⋯O1iii	0.96	2.58	3.4899 (14)	158
C16—H16C⋯Cg1iv	0.96	2.82	3.6137 (14)	135

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .