3-[(E)-3-(2,4-Dichloro-phen-yl)prop-2-en-oyl]-4-hy-droxy-2H-chromen-2-one.

In the title compound, C(18)H(10)Cl(2)O(4), the chromen-2-one ring system is almost planar [maximum deviation = 0.028 (1) Å] and is inclined at an angle of 16.35 (4)° with respect to the benzene ring. The C=C bond has an E configuration. The mol-ecular conformation is stabilized by an almost symmetric intra-molecular O⋯H⋯O hydrogen bond and a C-H⋯O inter-action, both of which form S(6) ring motifs. In the crystal structure, mol-ecules are linked into sheets lying parallel to (100) via inter-molecular C-H⋯O hydrogen bonds. The crystal packing is further consolidated by π-π stacking inter-actions [centroid-to-centroid separation = 3.6615 (6) Å].

Related literature

For general background to and the biological activity of chalcones, see: Claisen et al. (1881 ▶); Siddiqui et al. (2008 ▶); Harborne & Mabry (1982 ▶); Bandgar et al. (2010 ▶). For related structures, see: Arshad et al. (2010 ▶); Asad et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C18H10Cl2O4

M = 361.16

Monoclinic,

a = 4.5233 (2) Å

b = 21.2099 (9) Å

c = 15.6304 (7) Å

β = 91.607 (1)°

V = 1498.97 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.45 mm−1

T = 100 K

0.35 × 0.15 × 0.09 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.857, T max = 0.959

25117 measured reflections

6698 independent reflections

5270 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.101

S = 1.05

6698 reflections

222 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.54 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810043837/hb5700sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043837/hb5700Isup2.hkl

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

C18H10Cl2O4	F(000) = 736
Mr = 361.16	Dx = 1.600 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9100 reflections
a = 4.5233 (2) Å	θ = 2.3–35.1°
b = 21.2099 (9) Å	µ = 0.45 mm−1
c = 15.6304 (7) Å	T = 100 K
β = 91.607 (1)°	Needle, yellow
V = 1498.97 (11) Å3	0.35 × 0.15 × 0.09 mm
Z = 4

Bruker SMART APEXII DUO CCD diffractometer	6698 independent reflections
Radiation source: fine-focus sealed tube	5270 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 35.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
Tmin = 0.857, Tmax = 0.959	k = −27→34
25117 measured reflections	l = −25→22

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) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0509P)2 + 0.2749P] where P = (Fo2 + 2Fc2)/3
6698 reflections	(Δ/σ)max = 0.001
222 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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 > 2sigma(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	−0.68600 (6)	0.640460 (12)	0.153533 (17)	0.02236 (7)
Cl2	−0.07973 (6)	0.434153 (13)	0.069793 (16)	0.02180 (7)
O1	0.69790 (16)	0.35450 (4)	0.57063 (5)	0.01808 (14)
O2	0.37593 (19)	0.41872 (4)	0.51001 (5)	0.02516 (17)
O3	0.96509 (16)	0.28446 (4)	0.34161 (5)	0.01797 (14)
O4	0.63677 (16)	0.35486 (4)	0.26596 (5)	0.01701 (14)
C1	0.5646 (2)	0.37989 (5)	0.49758 (6)	0.01664 (17)
C2	0.9014 (2)	0.30666 (5)	0.56843 (6)	0.01535 (17)
C3	1.0072 (2)	0.28411 (5)	0.64694 (7)	0.01883 (18)
H3A	0.9402	0.3009	0.6978	0.023*
C4	1.2149 (2)	0.23600 (5)	0.64775 (7)	0.02067 (19)
H4A	1.2889	0.2207	0.6998	0.025*
C5	1.3149 (2)	0.21011 (5)	0.57151 (7)	0.02046 (19)
H5A	1.4544	0.1779	0.5731	0.025*
C6	1.2059 (2)	0.23256 (5)	0.49397 (7)	0.01786 (18)
H6A	1.2708	0.2153	0.4431	0.021*
C7	0.9967 (2)	0.28162 (5)	0.49195 (6)	0.01467 (16)
C8	0.87645 (19)	0.30746 (4)	0.41294 (6)	0.01417 (16)
C9	0.6643 (2)	0.35648 (4)	0.41544 (6)	0.01407 (16)
C10	0.54393 (19)	0.37953 (5)	0.33533 (6)	0.01447 (16)
C11	0.3233 (2)	0.42963 (5)	0.32717 (6)	0.01642 (17)
H11A	0.2750	0.4541	0.3742	0.020*
C12	0.1915 (2)	0.43961 (5)	0.25011 (6)	0.01545 (17)
H12A	0.2476	0.4133	0.2058	0.019*
C13	−0.0299 (2)	0.48736 (5)	0.22909 (6)	0.01444 (16)
C14	−0.1625 (2)	0.49008 (5)	0.14673 (6)	0.01522 (16)
C15	−0.3651 (2)	0.53657 (5)	0.12291 (6)	0.01714 (17)
H15A	−0.4475	0.5379	0.0677	0.021*
C16	−0.4410 (2)	0.58096 (5)	0.18364 (7)	0.01636 (17)
C17	−0.3254 (2)	0.57894 (5)	0.26670 (7)	0.01765 (17)
H17A	−0.3843	0.6082	0.3072	0.021*
C18	−0.1210 (2)	0.53266 (5)	0.28840 (6)	0.01714 (17)
H18A	−0.0415	0.5315	0.3439	0.021*
H1O	0.812 (5)	0.3171 (11)	0.2882 (15)	0.077 (7)*

	U11	U22	U33	U12	U13	U23
Cl1	0.02114 (11)	0.01919 (12)	0.02702 (13)	0.00611 (8)	0.00565 (9)	0.00516 (9)
Cl2	0.02795 (12)	0.02120 (13)	0.01605 (11)	0.00727 (9)	−0.00287 (8)	−0.00406 (9)
O1	0.0216 (3)	0.0197 (4)	0.0130 (3)	0.0062 (3)	0.0009 (2)	0.0002 (3)
O2	0.0307 (4)	0.0272 (4)	0.0177 (4)	0.0140 (3)	0.0026 (3)	0.0002 (3)
O3	0.0201 (3)	0.0190 (3)	0.0149 (3)	0.0025 (3)	0.0016 (2)	−0.0027 (3)
O4	0.0179 (3)	0.0202 (4)	0.0130 (3)	0.0002 (2)	−0.0004 (2)	−0.0016 (3)
C1	0.0194 (4)	0.0166 (4)	0.0139 (4)	0.0014 (3)	0.0001 (3)	0.0004 (3)
C2	0.0154 (4)	0.0149 (4)	0.0157 (4)	0.0007 (3)	0.0009 (3)	0.0016 (3)
C3	0.0196 (4)	0.0212 (5)	0.0157 (4)	0.0006 (3)	0.0005 (3)	0.0030 (4)
C4	0.0194 (4)	0.0220 (5)	0.0204 (5)	0.0004 (4)	−0.0016 (3)	0.0068 (4)
C5	0.0181 (4)	0.0179 (5)	0.0254 (5)	0.0025 (3)	0.0000 (3)	0.0038 (4)
C6	0.0169 (4)	0.0161 (4)	0.0206 (4)	0.0007 (3)	0.0016 (3)	−0.0001 (4)
C7	0.0150 (4)	0.0137 (4)	0.0154 (4)	−0.0010 (3)	0.0009 (3)	0.0007 (3)
C8	0.0140 (4)	0.0140 (4)	0.0146 (4)	−0.0021 (3)	0.0009 (3)	−0.0007 (3)
C9	0.0147 (4)	0.0150 (4)	0.0125 (4)	−0.0001 (3)	0.0004 (3)	0.0002 (3)
C10	0.0135 (4)	0.0147 (4)	0.0152 (4)	−0.0027 (3)	−0.0004 (3)	0.0000 (3)
C11	0.0164 (4)	0.0167 (4)	0.0161 (4)	0.0000 (3)	−0.0008 (3)	0.0006 (3)
C12	0.0148 (4)	0.0158 (4)	0.0156 (4)	−0.0012 (3)	−0.0005 (3)	0.0006 (3)
C13	0.0146 (4)	0.0150 (4)	0.0138 (4)	−0.0014 (3)	0.0004 (3)	0.0010 (3)
C14	0.0165 (4)	0.0156 (4)	0.0135 (4)	0.0001 (3)	0.0008 (3)	−0.0009 (3)
C15	0.0173 (4)	0.0181 (5)	0.0160 (4)	0.0013 (3)	−0.0001 (3)	0.0008 (3)
C16	0.0148 (4)	0.0145 (4)	0.0200 (4)	0.0007 (3)	0.0037 (3)	0.0021 (3)
C17	0.0187 (4)	0.0164 (4)	0.0179 (4)	−0.0005 (3)	0.0035 (3)	−0.0017 (3)
C18	0.0179 (4)	0.0181 (4)	0.0154 (4)	−0.0013 (3)	0.0004 (3)	−0.0012 (3)

Cl1—C16	1.7358 (10)	C6—H6A	0.9300
Cl2—C14	1.7376 (10)	C7—C8	1.4436 (13)
O1—C2	1.3711 (12)	C8—C9	1.4162 (13)
O1—C1	1.3851 (12)	C9—C10	1.4371 (13)
O2—C1	1.2059 (12)	C10—C11	1.4610 (13)
O3—C8	1.2910 (11)	C11—C12	1.3457 (13)
O3—H1O	1.27 (2)	C11—H11A	0.9300
O4—C10	1.2851 (12)	C12—C13	1.4554 (13)
O4—H1O	1.17 (2)	C12—H12A	0.9300
C1—C9	1.4595 (13)	C13—C18	1.4050 (14)
C2—C7	1.3877 (14)	C13—C14	1.4061 (13)
C2—C3	1.3895 (14)	C14—C15	1.3896 (13)
C3—C4	1.3869 (15)	C15—C16	1.3870 (14)
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.3988 (16)	C16—C17	1.3867 (14)
C4—H4A	0.9300	C17—C18	1.3841 (14)
C5—C6	1.3804 (15)	C17—H17A	0.9300
C5—H5A	0.9300	C18—H18A	0.9300
C6—C7	1.4062 (13)
C2—O1—C1	122.95 (8)	C10—C9—C1	122.14 (8)
C8—O3—H1O	100.6 (11)	O4—C10—C9	118.16 (9)
C10—O4—H1O	105.2 (12)	O4—C10—C11	117.46 (8)
O2—C1—O1	115.24 (9)	C9—C10—C11	124.38 (9)
O2—C1—C9	127.70 (9)	C12—C11—C10	118.48 (9)
O1—C1—C9	117.06 (8)	C12—C11—H11A	120.8
O1—C2—C7	122.00 (8)	C10—C11—H11A	120.8
O1—C2—C3	116.57 (9)	C11—C12—C13	126.60 (9)
C7—C2—C3	121.43 (9)	C11—C12—H12A	116.7
C4—C3—C2	118.53 (10)	C13—C12—H12A	116.7
C4—C3—H3A	120.7	C18—C13—C14	116.78 (9)
C2—C3—H3A	120.7	C18—C13—C12	122.66 (8)
C3—C4—C5	121.09 (9)	C14—C13—C12	120.56 (9)
C3—C4—H4A	119.5	C15—C14—C13	122.39 (9)
C5—C4—H4A	119.5	C15—C14—Cl2	116.89 (7)
C6—C5—C4	119.76 (9)	C13—C14—Cl2	120.72 (7)
C6—C5—H5A	120.1	C16—C15—C14	118.18 (9)
C4—C5—H5A	120.1	C16—C15—H15A	120.9
C5—C6—C7	119.91 (9)	C14—C15—H15A	120.9
C5—C6—H6A	120.0	C17—C16—C15	121.71 (9)
C7—C6—H6A	120.0	C17—C16—Cl1	119.83 (8)
C2—C7—C6	119.27 (9)	C15—C16—Cl1	118.46 (8)
C2—C7—C8	118.22 (8)	C18—C17—C16	118.89 (9)
C6—C7—C8	122.51 (9)	C18—C17—H17A	120.6
O3—C8—C9	121.89 (9)	C16—C17—H17A	120.6
O3—C8—C7	118.46 (8)	C17—C18—C13	121.97 (9)
C9—C8—C7	119.64 (8)	C17—C18—H18A	119.0
C8—C9—C10	117.78 (8)	C13—C18—H18A	119.0
C8—C9—C1	120.01 (8)
C2—O1—C1—O2	175.23 (9)	O2—C1—C9—C10	1.19 (16)
C2—O1—C1—C9	−4.08 (14)	O1—C1—C9—C10	−179.59 (8)
C1—O1—C2—C7	2.35 (14)	C8—C9—C10—O4	−0.56 (13)
C1—O1—C2—C3	−177.35 (9)	C1—C9—C10—O4	−177.65 (9)
O1—C2—C3—C4	−179.58 (9)	C8—C9—C10—C11	179.82 (9)
C7—C2—C3—C4	0.72 (15)	C1—C9—C10—C11	2.74 (14)
C2—C3—C4—C5	−0.55 (16)	O4—C10—C11—C12	11.55 (13)
C3—C4—C5—C6	−0.03 (16)	C9—C10—C11—C12	−168.83 (9)
C4—C5—C6—C7	0.47 (15)	C10—C11—C12—C13	−179.31 (9)
O1—C2—C7—C6	−179.98 (9)	C11—C12—C13—C18	4.13 (15)
C3—C2—C7—C6	−0.30 (15)	C11—C12—C13—C14	−176.17 (9)
O1—C2—C7—C8	0.23 (14)	C18—C13—C14—C15	2.61 (14)
C3—C2—C7—C8	179.92 (9)	C12—C13—C14—C15	−177.10 (9)
C5—C6—C7—C2	−0.31 (14)	C18—C13—C14—Cl2	−176.94 (7)
C5—C6—C7—C8	179.47 (9)	C12—C13—C14—Cl2	3.35 (13)
C2—C7—C8—O3	179.79 (9)	C13—C14—C15—C16	−1.12 (14)
C6—C7—C8—O3	0.01 (14)	Cl2—C14—C15—C16	178.44 (7)
C2—C7—C8—C9	−0.80 (13)	C14—C15—C16—C17	−1.44 (14)
C6—C7—C8—C9	179.43 (9)	C14—C15—C16—Cl1	178.24 (7)
O3—C8—C9—C10	1.20 (13)	C15—C16—C17—C18	2.35 (15)
C7—C8—C9—C10	−178.19 (8)	Cl1—C16—C17—C18	−177.32 (8)
O3—C8—C9—C1	178.35 (9)	C16—C17—C18—C13	−0.73 (15)
C7—C8—C9—C1	−1.04 (13)	C14—C13—C18—C17	−1.66 (14)
O2—C1—C9—C8	−175.83 (10)	C12—C13—C18—C17	178.05 (9)
O1—C1—C9—C8	3.39 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O···O4	1.27 (2)	1.17 (2)	2.3947 (11)	156 (2)
C11—H11A···O2	0.93	2.29	2.8704 (12)	120
C4—H4A···O4i	0.93	2.45	3.2514 (13)	144
C17—H17A···O1ii	0.93	2.54	3.3966 (13)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O⋯O4	1.27 (2)	1.17 (2)	2.3947 (11)	156 (2)
C11—H11A⋯O2	0.93	2.29	2.8704 (12)	120
C4—H4A⋯O4i	0.93	2.45	3.2514 (13)	144
C17—H17A⋯O1ii	0.93	2.54	3.3966 (13)	154

Symmetry codes: (i) ; (ii) .