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

In the title compound, C(15)H(11)ClO(2), the dihedral angle between the mean planes of the chloro-benzene and hy-droxy-benzene rings is 6.5 (6)°. The mean plane of the prop-2-en-1-one group makes an angle of 18.0 (1)° with the hy-droxy-phenyl ring and 11.5 (1)° with the chloro-phenyl ring. The crystal packing is stabilized by inter-molecular O-H⋯O hydrogen bonds, weak C-H⋯O, C-H⋯π and π-π stacking inter-actions [centroid-centroid distances = 3.7771 (7) and 3.6917 (7) Å].

Related literature

For the biological properties of chalcones, see: Nowakowska (2007 ▶) and for their role in tubulin polymerization inhibition, see: Edwards et al. (1989 ▶). For related structures, see: Jasinski et al. (2010 ▶, 2011a ▶,b ▶); Butcher et al. (2007a ▶,b ▶); Narayana et al. (2007 ▶); Sarojini et al. (2007a ▶,b ▶). For standard bond lengths, see: Allen et al., (1987 ▶).

Experimental

Crystal data

C15H11ClO2

M = 258.69

Monoclinic,

a = 7.3570 (2) Å

b = 15.6450 (5) Å

c = 10.4954 (3) Å

β = 90.518 (3)°

V = 1207.97 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 200 K

0.51 × 0.45 × 0.36 mm

Data collection

Oxford Diffraction Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.984, T max = 1.000

10126 measured reflections

4020 independent reflections

2924 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.115

S = 1.07

4020 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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/S160053681100701X/sj5108sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100701X/sj5108Isup2.hkl

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

C15H11ClO2	F(000) = 536
Mr = 258.69	Dx = 1.422 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4738 reflections
a = 7.3570 (2) Å	θ = 4.7–32.4°
b = 15.6450 (5) Å	µ = 0.31 mm−1
c = 10.4954 (3) Å	T = 200 K
β = 90.518 (3)°	Irregular chunk, colorless
V = 1207.97 (6) Å3	0.51 × 0.45 × 0.36 mm
Z = 4

Oxford Diffraction Gemini diffractometer	4020 independent reflections
Radiation source: fine-focus sealed tube	2924 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 10.5081 pixels mm-1	θmax = 32.6°, θmin = 4.7°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −23→17
Tmin = 0.984, Tmax = 1.000	l = −11→15
10126 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0648P)2] where P = (Fo2 + 2Fc2)/3
4020 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.18 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	0.13335 (5)	0.12309 (2)	0.03417 (3)	0.03910 (12)
O1	0.83226 (11)	−0.31714 (6)	−0.88736 (8)	0.0269 (2)
H1O	0.7288	−0.3393	−0.8952	0.032*
O2	1.03166 (11)	−0.08981 (6)	−0.40899 (9)	0.0300 (2)
C1	0.86149 (15)	−0.16357 (7)	−0.56445 (10)	0.0217 (2)
C2	1.01626 (15)	−0.18219 (7)	−0.63990 (11)	0.0233 (2)
H2A	1.1307	−0.1587	−0.6162	0.028*
C3	1.00442 (15)	−0.23337 (7)	−0.74638 (11)	0.0240 (2)
H3A	1.1090	−0.2440	−0.7964	0.029*
C4	0.83821 (15)	−0.26923 (7)	−0.77995 (11)	0.0218 (2)
C5	0.68456 (15)	−0.25387 (8)	−0.70399 (11)	0.0249 (2)
H5A	0.5718	−0.2800	−0.7253	0.030*
C6	0.69667 (15)	−0.20111 (8)	−0.59876 (11)	0.0250 (2)
H6A	0.5916	−0.1903	−0.5494	0.030*
C7	0.88030 (15)	−0.10548 (7)	−0.45464 (11)	0.0228 (2)
C8	0.71613 (16)	−0.06563 (8)	−0.39876 (11)	0.0257 (2)
H8A	0.5998	−0.0789	−0.4335	0.031*
C9	0.72854 (16)	−0.01152 (7)	−0.30074 (11)	0.0244 (2)
H9A	0.8482	0.0042	−0.2753	0.029*
C10	0.57985 (15)	0.02682 (7)	−0.22700 (11)	0.0232 (2)
C11	0.39739 (16)	0.00729 (8)	−0.25006 (12)	0.0269 (3)
H11A	0.3655	−0.0270	−0.3215	0.032*
C12	0.26083 (16)	0.03728 (8)	−0.16994 (12)	0.0286 (3)
H12A	0.1376	0.0221	−0.1856	0.034*
C13	0.30593 (17)	0.08902 (8)	−0.06791 (11)	0.0267 (3)
C14	0.48422 (18)	0.11178 (8)	−0.04434 (12)	0.0296 (3)
H14A	0.5144	0.1483	0.0250	0.036*
C15	0.61975 (17)	0.08026 (8)	−0.12423 (12)	0.0277 (3)
H15A	0.7427	0.0957	−0.1080	0.033*

	U11	U22	U33	U12	U13	U23
Cl	0.0429 (2)	0.0418 (2)	0.03272 (18)	0.01436 (15)	0.01185 (14)	0.00176 (13)
O1	0.0232 (4)	0.0314 (5)	0.0261 (4)	−0.0042 (3)	0.0043 (3)	−0.0055 (3)
O2	0.0223 (4)	0.0345 (5)	0.0330 (5)	0.0028 (4)	−0.0034 (3)	−0.0045 (4)
C1	0.0207 (5)	0.0229 (5)	0.0216 (5)	0.0009 (4)	0.0022 (4)	0.0022 (4)
C2	0.0175 (5)	0.0265 (6)	0.0259 (6)	−0.0006 (4)	0.0006 (4)	0.0022 (5)
C3	0.0190 (5)	0.0280 (6)	0.0250 (6)	0.0004 (4)	0.0053 (4)	0.0015 (4)
C4	0.0236 (5)	0.0218 (5)	0.0203 (5)	0.0008 (4)	0.0022 (4)	0.0034 (4)
C5	0.0185 (5)	0.0296 (6)	0.0265 (6)	−0.0049 (4)	0.0031 (4)	0.0009 (5)
C6	0.0204 (5)	0.0296 (6)	0.0250 (6)	−0.0003 (4)	0.0057 (4)	0.0003 (5)
C7	0.0219 (5)	0.0241 (6)	0.0226 (5)	0.0012 (4)	0.0013 (4)	0.0033 (4)
C8	0.0203 (5)	0.0312 (6)	0.0257 (6)	0.0018 (5)	−0.0001 (4)	−0.0020 (5)
C9	0.0221 (5)	0.0250 (6)	0.0262 (6)	−0.0004 (4)	−0.0004 (4)	0.0004 (5)
C10	0.0243 (5)	0.0210 (5)	0.0241 (5)	0.0009 (4)	0.0001 (4)	−0.0003 (4)
C11	0.0265 (6)	0.0274 (6)	0.0267 (6)	0.0013 (5)	−0.0025 (5)	−0.0048 (5)
C12	0.0226 (6)	0.0319 (6)	0.0312 (6)	0.0027 (5)	−0.0010 (5)	−0.0002 (5)
C13	0.0311 (6)	0.0239 (6)	0.0251 (6)	0.0074 (5)	0.0041 (5)	0.0028 (5)
C14	0.0381 (7)	0.0244 (6)	0.0263 (6)	0.0012 (5)	−0.0021 (5)	−0.0048 (5)
C15	0.0273 (6)	0.0268 (6)	0.0290 (6)	−0.0029 (5)	−0.0031 (5)	−0.0029 (5)

Cl—C13	1.7517 (12)	C7—C8	1.4846 (15)
O1—C4	1.3541 (14)	C8—C9	1.3348 (16)
O1—H1O	0.8400	C8—H8A	0.9500
O2—C7	1.2328 (14)	C9—C10	1.4734 (15)
C1—C6	1.3917 (16)	C9—H9A	0.9500
C1—C2	1.4230 (14)	C10—C15	1.3939 (16)
C1—C7	1.4733 (16)	C10—C11	1.3957 (17)
C2—C3	1.3770 (16)	C11—C12	1.3971 (16)
C2—H2A	0.9500	C11—H11A	0.9500
C3—C4	1.3879 (16)	C12—C13	1.3804 (18)
C3—H3A	0.9500	C12—H12A	0.9500
C4—C5	1.4098 (15)	C13—C14	1.3793 (18)
C5—C6	1.3811 (17)	C14—C15	1.3984 (17)
C5—H5A	0.9500	C14—H14A	0.9500
C6—H6A	0.9500	C15—H15A	0.9500
C4—O1—H1O	109.5	C9—C8—H8A	119.3
C6—C1—C2	117.99 (10)	C7—C8—H8A	119.3
C6—C1—C7	122.56 (10)	C8—C9—C10	128.11 (11)
C2—C1—C7	119.45 (10)	C8—C9—H9A	115.9
C3—C2—C1	121.71 (10)	C10—C9—H9A	115.9
C3—C2—H2A	119.1	C15—C10—C11	117.45 (10)
C1—C2—H2A	119.1	C15—C10—C9	119.90 (11)
C2—C3—C4	119.35 (10)	C11—C10—C9	122.49 (11)
C2—C3—H3A	120.3	C10—C11—C12	121.18 (11)
C4—C3—H3A	120.3	C10—C11—H11A	119.4
O1—C4—C3	117.18 (10)	C12—C11—H11A	119.4
O1—C4—C5	123.03 (10)	C13—C12—C11	119.66 (11)
C3—C4—C5	119.78 (10)	C13—C12—H12A	120.2
C6—C5—C4	120.52 (11)	C11—C12—H12A	120.2
C6—C5—H5A	119.7	C14—C13—C12	120.79 (11)
C4—C5—H5A	119.7	C14—C13—Cl	120.34 (10)
C5—C6—C1	120.59 (10)	C12—C13—Cl	118.84 (10)
C5—C6—H6A	119.7	C13—C14—C15	118.92 (12)
C1—C6—H6A	119.7	C13—C14—H14A	120.5
O2—C7—C1	120.32 (10)	C15—C14—H14A	120.5
O2—C7—C8	119.88 (11)	C10—C15—C14	121.95 (11)
C1—C7—C8	119.80 (10)	C10—C15—H15A	119.0
C9—C8—C7	121.37 (11)	C14—C15—H15A	119.0
C6—C1—C2—C3	2.13 (17)	C1—C7—C8—C9	−178.78 (11)
C7—C1—C2—C3	−177.42 (11)	C7—C8—C9—C10	−173.67 (11)
C1—C2—C3—C4	−1.28 (17)	C8—C9—C10—C15	177.89 (12)
C2—C3—C4—O1	178.21 (10)	C8—C9—C10—C11	2.43 (19)
C2—C3—C4—C5	−0.86 (17)	C15—C10—C11—C12	−2.62 (18)
O1—C4—C5—C6	−176.85 (11)	C9—C10—C11—C12	172.94 (12)
C3—C4—C5—C6	2.17 (18)	C10—C11—C12—C13	1.71 (19)
C4—C5—C6—C1	−1.29 (18)	C11—C12—C13—C14	0.26 (19)
C2—C1—C6—C5	−0.81 (17)	C11—C12—C13—Cl	−178.00 (10)
C7—C1—C6—C5	178.72 (11)	C12—C13—C14—C15	−1.18 (19)
C6—C1—C7—O2	162.67 (11)	Cl—C13—C14—C15	177.05 (10)
C2—C1—C7—O2	−17.81 (17)	C11—C10—C15—C14	1.68 (18)
C6—C1—C7—C8	−17.34 (17)	C9—C10—C15—C14	−174.00 (11)
C2—C1—C7—C8	162.18 (11)	C13—C14—C15—C10	0.19 (19)
O2—C7—C8—C9	1.20 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2i	0.84	1.83	2.6556 (12)	167
C6—H6A···O1ii	0.95	2.57	3.5070 (13)	169
C11—H11A···O1ii	0.95	2.55	3.3382 (15)	141
C14—H14A···Cg1iii	0.95	2.79	3.7090 (14)	163

CgI···CgJ	Cg···Cg (Å)	CgI Perp (Å)	Cgj Perp (Å)	Slippage (Å)
Cg1···Cg2i	3.7771 (7)	3.3144 (5)	3.4958 (5)
Cg2···Cg2ii	3.6917 (7)	-3.3684 (5)	-3.3683 (5)	1.51 (1)

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
O1—H1O⋯O2i	0.84	1.83	2.6556 (12)	167
C6—H6A⋯O1ii	0.95	2.57	3.5070 (13)	169
C11—H11A⋯O1ii	0.95	2.55	3.3382 (15)	141
C14—H14A⋯Cg1iii	0.95	2.79	3.7090 (14)	163

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