(E)-2-(3-Chloro-benzyl-idene)-5,6-dimeth-oxy-2,3-dihydro-1H-inden-1-one.

In the title compound, C(18)H(15)ClO(3), the dihydro-indenone group makes a dihedral angle of 8.56 (6)° with the bezene ring. In the crystal, the mol-ecules are inter-connected into a three-dimensional network via inter-molecular C-H⋯O hydrogen bonds. Weak C-H⋯π and π⋯π [centroid-centroid distances 3.6598 (9)-3.6913 (9) Å] inter-actions are also observed.

Related literature

For general background to and the biological activity of chalcone derivatives, see: Marzinzik & Felder (1998 ▶); Srikanth & Castle (2005 ▶); Furusawa et al. (2005 ▶) Heidenreich et al. (2008 ▶); Syed et al. (2008 ▶). For related structures, see: Ali et al. (2010a ▶,b ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C18H15ClO3

M = 314.75

Tetragonal,

a = 20.5004 (16) Å

c = 7.0241 (7) Å

V = 2952.0 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.27 mm−1

T = 100 K

0.74 × 0.13 × 0.11 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.826, T max = 0.971

62722 measured reflections

4499 independent reflections

4251 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.084

S = 1.06

4499 reflections

259 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 1966 Friedel pairs

Flack parameter: −0.01 (5)

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/S1600536810040869/sj5044sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040869/sj5044Isup2.hkl

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

C18H15ClO3	Dx = 1.416 Mg m−3
Mr = 314.75	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P421c	Cell parameters from 9872 reflections
Hall symbol: P -4 2n	θ = 2.8–30.4°
a = 20.5004 (16) Å	µ = 0.27 mm−1
c = 7.0241 (7) Å	T = 100 K
V = 2952.0 (4) Å3	Needle, yellow
Z = 8	0.74 × 0.13 × 0.11 mm
F(000) = 1312

Bruker APEXII DUO CCD area-detector diffractometer	4499 independent reflections
Radiation source: fine-focus sealed tube	4251 reflections with I > 2σ(I)
graphite	Rint = 0.045
φ and ω scans	θmax = 30.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −29→29
Tmin = 0.826, Tmax = 0.971	k = −28→29
62722 measured reflections	l = −10→10

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)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084	w = 1/[σ2(Fo2) + (0.0483P)2 + 0.5709P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
4499 reflections	Δρmax = 0.37 e Å−3
259 parameters	Δρmin = −0.19 e Å−3
0 restraints	Absolute structure: Flack (1983), 1966 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.01 (5)

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

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	0.658402 (17)	0.24083 (2)	0.07331 (5)	0.03382 (9)
O1	0.35460 (5)	0.18458 (5)	0.76502 (14)	0.0273 (2)
O2	0.38949 (4)	0.34023 (5)	1.38581 (13)	0.02125 (18)
O3	0.49925 (5)	0.39341 (5)	1.30773 (13)	0.02196 (19)
C1	0.55261 (6)	0.20587 (6)	0.27855 (18)	0.0204 (2)
C2	0.59058 (6)	0.19228 (7)	0.11923 (18)	0.0235 (3)
C3	0.57575 (8)	0.14194 (8)	−0.0056 (2)	0.0300 (3)
C4	0.52078 (9)	0.10399 (8)	0.0310 (2)	0.0326 (3)
C5	0.48177 (8)	0.11719 (7)	0.1883 (2)	0.0275 (3)
C6	0.49729 (7)	0.16787 (6)	0.31451 (17)	0.0206 (2)
C7	0.45338 (6)	0.17840 (6)	0.47637 (17)	0.0207 (2)
C8	0.45819 (6)	0.21831 (6)	0.62791 (17)	0.0183 (2)
C9	0.40455 (6)	0.21715 (6)	0.77302 (17)	0.0190 (2)
C10	0.42366 (6)	0.26270 (6)	0.92367 (16)	0.0166 (2)
C11	0.38957 (6)	0.27681 (6)	1.09221 (17)	0.0173 (2)
C12	0.41636 (6)	0.32139 (6)	1.21623 (17)	0.0169 (2)
C13	0.47750 (6)	0.35135 (6)	1.17248 (16)	0.0168 (2)
C14	0.51055 (6)	0.33681 (6)	1.00419 (17)	0.0168 (2)
C15	0.48283 (6)	0.29164 (6)	0.87923 (16)	0.0156 (2)
C16	0.50915 (6)	0.26751 (6)	0.68977 (16)	0.0178 (2)
C17	0.32745 (6)	0.31173 (7)	1.4304 (2)	0.0237 (2)
C18	0.55815 (7)	0.42822 (7)	1.2670 (2)	0.0266 (3)
H1	0.5664 (9)	0.2390 (9)	0.359 (3)	0.029 (5)*
H3	0.6019 (10)	0.1348 (10)	−0.102 (3)	0.044 (6)*
H4	0.5118 (11)	0.0700 (10)	−0.069 (4)	0.051 (6)*
H5	0.4430 (11)	0.0892 (10)	0.215 (3)	0.051 (6)*
H7	0.4154 (8)	0.1528 (8)	0.465 (3)	0.025 (4)*
H11	0.3500 (9)	0.2539 (8)	1.115 (3)	0.026 (4)*
H14	0.5503 (8)	0.3565 (9)	0.974 (3)	0.024 (4)*
H18A	0.5551 (10)	0.4571 (9)	1.158 (3)	0.031 (5)*
H18B	0.5953 (9)	0.3989 (9)	1.237 (3)	0.031 (5)*
H18C	0.5683 (11)	0.4553 (10)	1.375 (3)	0.047 (6)*
H16A	0.5126 (8)	0.3044 (8)	0.600 (3)	0.020 (4)*
H16B	0.5517 (8)	0.2491 (8)	0.703 (2)	0.020 (4)*
H17A	0.3144 (9)	0.3303 (9)	1.556 (3)	0.031 (5)*
H17B	0.2950 (8)	0.3251 (8)	1.341 (2)	0.020 (4)*
H17C	0.3292 (8)	0.2645 (8)	1.439 (3)	0.022 (4)*

	U11	U22	U33	U12	U13	U23
Cl1	0.02695 (16)	0.0484 (2)	0.02614 (16)	0.00242 (14)	0.00952 (13)	0.00399 (15)
O1	0.0264 (5)	0.0360 (5)	0.0195 (4)	−0.0121 (4)	0.0032 (4)	−0.0053 (4)
O2	0.0214 (4)	0.0246 (4)	0.0178 (4)	−0.0037 (3)	0.0070 (3)	−0.0051 (3)
O3	0.0234 (4)	0.0250 (4)	0.0175 (4)	−0.0077 (4)	0.0032 (3)	−0.0038 (3)
C1	0.0232 (6)	0.0233 (6)	0.0147 (5)	0.0064 (4)	0.0015 (4)	0.0019 (4)
C2	0.0227 (6)	0.0293 (6)	0.0184 (5)	0.0103 (5)	0.0031 (4)	0.0062 (5)
C3	0.0372 (8)	0.0338 (7)	0.0189 (5)	0.0146 (6)	0.0066 (6)	−0.0015 (5)
C4	0.0449 (8)	0.0292 (7)	0.0238 (6)	0.0079 (6)	0.0037 (6)	−0.0084 (5)
C5	0.0341 (7)	0.0271 (6)	0.0213 (6)	0.0015 (5)	0.0031 (5)	−0.0048 (5)
C6	0.0241 (6)	0.0228 (6)	0.0150 (5)	0.0053 (4)	0.0005 (4)	0.0008 (4)
C7	0.0234 (6)	0.0235 (6)	0.0154 (5)	0.0006 (5)	0.0024 (4)	−0.0003 (4)
C8	0.0197 (5)	0.0213 (5)	0.0139 (5)	−0.0001 (4)	0.0024 (4)	0.0001 (4)
C9	0.0205 (5)	0.0222 (5)	0.0144 (5)	−0.0021 (4)	0.0022 (4)	−0.0004 (4)
C10	0.0176 (5)	0.0191 (5)	0.0130 (4)	0.0002 (4)	0.0010 (4)	0.0005 (4)
C11	0.0173 (5)	0.0195 (5)	0.0152 (5)	−0.0011 (4)	0.0027 (4)	−0.0001 (4)
C12	0.0179 (5)	0.0182 (5)	0.0148 (5)	0.0008 (4)	0.0027 (4)	0.0006 (4)
C13	0.0184 (5)	0.0172 (5)	0.0150 (5)	0.0000 (4)	−0.0003 (4)	0.0011 (4)
C14	0.0155 (5)	0.0186 (5)	0.0163 (4)	0.0004 (4)	0.0003 (4)	0.0013 (4)
C15	0.0166 (5)	0.0180 (5)	0.0122 (4)	0.0018 (4)	0.0012 (4)	0.0015 (4)
C16	0.0183 (5)	0.0216 (5)	0.0136 (5)	0.0005 (4)	0.0037 (4)	0.0004 (4)
C17	0.0206 (6)	0.0310 (6)	0.0195 (5)	−0.0026 (5)	0.0064 (5)	−0.0010 (5)
C18	0.0240 (6)	0.0327 (7)	0.0232 (6)	−0.0098 (5)	0.0013 (5)	−0.0047 (5)

Cl1—C2	1.7401 (15)	C8—C16	1.5160 (17)
O1—C9	1.2237 (15)	C9—C10	1.4647 (16)
O2—C12	1.3680 (14)	C10—C15	1.3860 (16)
O2—C17	1.4343 (15)	C10—C11	1.4048 (16)
O3—C13	1.3582 (14)	C11—C12	1.3768 (17)
O3—C18	1.4314 (16)	C11—H11	0.951 (18)
C1—C2	1.3914 (17)	C12—C13	1.4293 (16)
C1—C6	1.3988 (19)	C13—C14	1.3948 (16)
C1—H1	0.926 (19)	C14—C15	1.3968 (16)
C2—C3	1.388 (2)	C14—H14	0.935 (17)
C3—C4	1.393 (2)	C15—C16	1.5188 (16)
C3—H3	0.87 (2)	C16—H16A	0.989 (17)
C4—C5	1.390 (2)	C16—H16B	0.955 (17)
C4—H4	1.01 (2)	C17—H17A	0.994 (19)
C5—C6	1.4025 (18)	C17—H17B	0.953 (17)
C5—H5	1.00 (2)	C17—H17C	0.971 (17)
C6—C7	1.4661 (17)	C18—H18A	0.97 (2)
C7—C8	1.3461 (17)	C18—H18B	0.994 (19)
C7—H7	0.943 (17)	C18—H18C	0.96 (2)
C8—C9	1.4995 (16)
C12—O2—C17	115.60 (10)	C12—C11—H11	124.0 (11)
C13—O3—C18	116.98 (10)	C10—C11—H11	117.8 (11)
C2—C1—C6	119.16 (12)	O2—C12—C11	125.30 (11)
C2—C1—H1	117.7 (12)	O2—C12—C13	114.76 (10)
C6—C1—H1	123.1 (12)	C11—C12—C13	119.94 (11)
C3—C2—C1	122.31 (14)	O3—C13—C14	124.68 (11)
C3—C2—Cl1	118.89 (11)	O3—C13—C12	114.23 (10)
C1—C2—Cl1	118.79 (11)	C14—C13—C12	121.09 (11)
C2—C3—C4	118.40 (13)	C13—C14—C15	118.47 (11)
C2—C3—H3	118.6 (14)	C13—C14—H14	121.7 (12)
C4—C3—H3	123.0 (14)	C15—C14—H14	119.9 (12)
C5—C4—C3	120.22 (14)	C10—C15—C14	119.89 (11)
C5—C4—H4	125.7 (14)	C10—C15—C16	111.65 (10)
C3—C4—H4	113.9 (14)	C14—C15—C16	128.46 (11)
C4—C5—C6	121.06 (14)	C8—C16—C15	102.88 (9)
C4—C5—H5	119.9 (13)	C8—C16—H16A	112.0 (10)
C6—C5—H5	119.0 (13)	C15—C16—H16A	109.8 (10)
C1—C6—C5	118.84 (12)	C8—C16—H16B	113.2 (10)
C1—C6—C7	123.76 (12)	C15—C16—H16B	111.7 (10)
C5—C6—C7	117.39 (12)	H16A—C16—H16B	107.4 (14)
C8—C7—C6	131.13 (12)	O2—C17—H17A	106.0 (11)
C8—C7—H7	117.8 (11)	O2—C17—H17B	111.0 (10)
C6—C7—H7	111.1 (11)	H17A—C17—H17B	106.4 (14)
C7—C8—C9	118.31 (11)	O2—C17—H17C	112.8 (10)
C7—C8—C16	132.96 (11)	H17A—C17—H17C	109.7 (15)
C9—C8—C16	108.73 (10)	H17B—C17—H17C	110.5 (14)
O1—C9—C10	127.22 (11)	O3—C18—H18A	114.1 (12)
O1—C9—C8	126.23 (11)	O3—C18—H18B	112.8 (11)
C10—C9—C8	106.55 (10)	H18A—C18—H18B	104.5 (15)
C15—C10—C11	122.49 (11)	O3—C18—H18C	108.2 (14)
C15—C10—C9	110.14 (10)	H18A—C18—H18C	106.5 (16)
C11—C10—C9	127.37 (11)	H18B—C18—H18C	110.5 (17)
C12—C11—C10	118.13 (11)
C6—C1—C2—C3	−0.32 (19)	C9—C10—C11—C12	179.81 (12)
C6—C1—C2—Cl1	178.78 (10)	C17—O2—C12—C11	−2.01 (17)
C1—C2—C3—C4	0.0 (2)	C17—O2—C12—C13	178.74 (11)
Cl1—C2—C3—C4	−179.06 (12)	C10—C11—C12—O2	−179.80 (11)
C2—C3—C4—C5	0.7 (2)	C10—C11—C12—C13	−0.59 (17)
C3—C4—C5—C6	−1.1 (2)	C18—O3—C13—C14	4.38 (18)
C2—C1—C6—C5	−0.09 (19)	C18—O3—C13—C12	−176.10 (11)
C2—C1—C6—C7	−179.15 (12)	O2—C12—C13—O3	0.50 (15)
C4—C5—C6—C1	0.8 (2)	C11—C12—C13—O3	−178.79 (11)
C4—C5—C6—C7	179.91 (14)	O2—C12—C13—C14	−179.96 (11)
C1—C6—C7—C8	−7.7 (2)	C11—C12—C13—C14	0.74 (18)
C5—C6—C7—C8	173.26 (14)	O3—C13—C14—C15	178.91 (11)
C6—C7—C8—C9	−179.20 (12)	C12—C13—C14—C15	−0.58 (17)
C6—C7—C8—C16	0.6 (2)	C11—C10—C15—C14	−0.16 (18)
C7—C8—C9—O1	−2.7 (2)	C9—C10—C15—C14	−179.73 (11)
C16—C8—C9—O1	177.46 (13)	C11—C10—C15—C16	179.72 (10)
C7—C8—C9—C10	177.72 (11)	C9—C10—C15—C16	0.15 (14)
C16—C8—C9—C10	−2.16 (13)	C13—C14—C15—C10	0.29 (17)
O1—C9—C10—C15	−178.36 (13)	C13—C14—C15—C16	−179.57 (11)
C8—C9—C10—C15	1.25 (13)	C7—C8—C16—C15	−177.69 (13)
O1—C9—C10—C11	2.1 (2)	C9—C8—C16—C15	2.15 (12)
C8—C9—C10—C11	−178.30 (11)	C10—C15—C16—C8	−1.44 (13)
C15—C10—C11—C12	0.32 (18)	C14—C15—C16—C8	178.43 (12)

Cg2 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1i	0.942 (16)	2.489 (18)	3.2650 (16)	139.6 (15)
C11—H11···O1ii	0.951 (18)	2.561 (17)	3.3229 (16)	137.3 (14)
C18—H18C···O3iii	0.96 (2)	2.53 (2)	3.4684 (17)	165.2 (17)
C3—H3···Cg2iv	0.87 (2)	2.86 (2)	3.6072 (17)	144.4 (17)

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1i	0.942 (16)	2.489 (18)	3.2650 (16)	139.6 (15)
C11—H11⋯O1ii	0.951 (18)	2.561 (17)	3.3229 (16)	137.3 (14)
C18—H18C⋯O3iii	0.96 (2)	2.53 (2)	3.4684 (17)	165.2 (17)
C3—H3⋯Cg2iv	0.87 (2)	2.86 (2)	3.6072 (17)	144.4 (17)

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