(E)-2-(3,4-Dimeth-oxy-benzyl-idene)-5,6-dimeth-oxy-2,3-dihydro-1H-inden-1-one.

In the title compound, C(20)H(20)O(5), the 2,3-dihydro-1H-indene ring system is essentially planar [maximum deviation = 0.010 (1) Å] and is inclined at an angle of 4.09 (4)° with respect to the phenyl ring. The C=C bond has an E configuration. In the crystal, the mol-ecules are linked into chains propagating in [102] via inter-molecular C-H⋯O hydrogen bonds. The crystal structure is further consolidated by C-H⋯π inter-actions.

Related literature

For general background to and the biological activity of chalcones, see: Nielsen et al. (1998 ▶); Go et al. (2005 ▶); Nowakowska (2007 ▶); Furusawa et al. (2005 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C20H20O5

M = 340.36

Monoclinic,

a = 7.7991 (7) Å

b = 7.2595 (6) Å

c = 29.589 (2) Å

β = 101.977 (3)°

V = 1638.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.53 × 0.45 × 0.09 mm

Data collection

Bruker APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.950, T max = 0.992

19303 measured reflections

5535 independent reflections

4471 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.124

S = 1.04

5535 reflections

230 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.21 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/S1600536810041619/hb5680sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041619/hb5680Isup2.hkl

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

C20H20O5	F(000) = 720
Mr = 340.36	Dx = 1.380 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6986 reflections
a = 7.7991 (7) Å	θ = 2.7–31.7°
b = 7.2595 (6) Å	µ = 0.10 mm−1
c = 29.589 (2) Å	T = 100 K
β = 101.977 (3)°	Plate, yellow
V = 1638.8 (2) Å3	0.53 × 0.45 × 0.09 mm
Z = 4

Bruker APEXII DUO CCD diffractometer	5535 independent reflections
Radiation source: fine-focus sealed tube	4471 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 31.8°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.950, Tmax = 0.992	k = −10→10
19303 measured reflections	l = −41→43

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0668P)2 + 0.3686P] where P = (Fo2 + 2Fc2)/3
5535 reflections	(Δ/σ)max = 0.002
230 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.21 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
O1	1.13991 (11)	0.89751 (10)	1.10930 (2)	0.02109 (16)
O2	1.10936 (10)	0.63257 (10)	1.16292 (2)	0.02089 (16)
O3	0.67192 (11)	0.17121 (11)	1.04585 (3)	0.02565 (18)
O4	0.20749 (12)	0.09725 (11)	0.79852 (3)	0.02789 (19)
O5	0.29534 (11)	0.38568 (11)	0.75804 (2)	0.02474 (18)
C1	0.73939 (12)	0.57231 (13)	0.97826 (3)	0.01539 (17)
H1A	0.8144	0.5695	0.9559	0.018*
H1B	0.6512	0.6672	0.9695	0.018*
C2	0.84490 (12)	0.60464 (13)	1.02641 (3)	0.01469 (17)
C3	0.94756 (13)	0.75715 (13)	1.04280 (3)	0.01598 (18)
H3A	0.9571	0.8557	1.0234	0.019*
C4	1.03547 (13)	0.75888 (13)	1.08879 (3)	0.01591 (18)
C5	1.01914 (13)	0.60926 (13)	1.11875 (3)	0.01583 (18)
C6	0.91645 (13)	0.45957 (13)	1.10221 (3)	0.01591 (17)
H6A	0.9045	0.3613	1.1215	0.019*
C7	0.83024 (12)	0.45901 (13)	1.05551 (3)	0.01495 (17)
C8	0.71294 (12)	0.31778 (13)	1.03029 (3)	0.01670 (18)
C9	0.65574 (12)	0.38678 (13)	0.98188 (3)	0.01564 (18)
C10	0.54838 (12)	0.28635 (13)	0.94942 (3)	0.01632 (18)
H10A	0.5090	0.1764	0.9598	0.020*
C11	0.48499 (12)	0.32517 (13)	0.90031 (3)	0.01607 (18)
C12	0.37662 (13)	0.19248 (13)	0.87386 (3)	0.01689 (18)
H12A	0.3464	0.0866	0.8881	0.020*
C13	0.31431 (14)	0.21748 (14)	0.82688 (3)	0.01865 (19)
C14	0.36029 (13)	0.37598 (14)	0.80457 (3)	0.01844 (19)
C15	0.46461 (14)	0.50818 (14)	0.83057 (3)	0.0205 (2)
H15A	0.4942	0.6143	0.8163	0.025*
C16	0.52578 (14)	0.48376 (14)	0.87797 (3)	0.0202 (2)
H16A	0.5948	0.5746	0.8950	0.024*
C17	1.16649 (16)	1.04933 (14)	1.08102 (4)	0.0240 (2)
H17A	1.2447	1.1362	1.0991	0.036*
H17B	1.0562	1.1080	1.0689	0.036*
H17C	1.2165	1.0061	1.0559	0.036*
C18	1.10498 (16)	0.48297 (16)	1.19368 (3)	0.0249 (2)
H18A	1.1819	0.5085	1.2228	0.037*
H18B	1.1425	0.3725	1.1808	0.037*
H18C	0.9876	0.4669	1.1983	0.037*
C19	0.14395 (17)	−0.05676 (16)	0.81966 (4)	0.0273 (2)
H19A	0.0667	−0.1276	0.7966	0.041*
H19B	0.0813	−0.0147	0.8424	0.041*
H19C	0.2408	−0.1322	0.8343	0.041*
C20	0.34068 (19)	0.54410 (17)	0.73445 (4)	0.0317 (3)
H20A	0.2863	0.5362	0.7023	0.048*
H20B	0.4656	0.5496	0.7377	0.048*
H20C	0.3006	0.6530	0.7475	0.048*

	U11	U22	U33	U12	U13	U23
O1	0.0295 (4)	0.0158 (3)	0.0161 (3)	−0.0051 (3)	0.0005 (3)	0.0003 (2)
O2	0.0289 (4)	0.0214 (3)	0.0106 (3)	−0.0031 (3)	−0.0002 (3)	0.0017 (2)
O3	0.0300 (4)	0.0223 (4)	0.0217 (3)	−0.0077 (3)	−0.0016 (3)	0.0067 (3)
O4	0.0412 (5)	0.0264 (4)	0.0150 (3)	−0.0166 (3)	0.0035 (3)	−0.0035 (3)
O5	0.0322 (4)	0.0277 (4)	0.0128 (3)	−0.0068 (3)	0.0013 (3)	0.0024 (3)
C1	0.0150 (4)	0.0183 (4)	0.0122 (3)	−0.0007 (3)	0.0014 (3)	0.0022 (3)
C2	0.0135 (4)	0.0174 (4)	0.0133 (4)	0.0013 (3)	0.0030 (3)	0.0009 (3)
C3	0.0189 (4)	0.0156 (4)	0.0132 (4)	0.0000 (3)	0.0029 (3)	0.0019 (3)
C4	0.0183 (4)	0.0147 (4)	0.0144 (4)	−0.0004 (3)	0.0026 (3)	−0.0006 (3)
C5	0.0181 (4)	0.0177 (4)	0.0114 (3)	0.0018 (3)	0.0022 (3)	0.0005 (3)
C6	0.0172 (4)	0.0168 (4)	0.0136 (4)	0.0004 (3)	0.0029 (3)	0.0022 (3)
C7	0.0143 (4)	0.0166 (4)	0.0136 (4)	0.0002 (3)	0.0021 (3)	0.0016 (3)
C8	0.0147 (4)	0.0189 (4)	0.0158 (4)	−0.0005 (3)	0.0017 (3)	0.0018 (3)
C9	0.0146 (4)	0.0179 (4)	0.0139 (4)	−0.0001 (3)	0.0018 (3)	0.0016 (3)
C10	0.0152 (4)	0.0181 (4)	0.0153 (4)	−0.0006 (3)	0.0025 (3)	0.0009 (3)
C11	0.0149 (4)	0.0183 (4)	0.0149 (4)	−0.0005 (3)	0.0027 (3)	−0.0006 (3)
C12	0.0196 (4)	0.0171 (4)	0.0146 (4)	−0.0019 (3)	0.0049 (3)	−0.0007 (3)
C13	0.0219 (5)	0.0188 (4)	0.0155 (4)	−0.0041 (4)	0.0045 (3)	−0.0035 (3)
C14	0.0198 (4)	0.0216 (4)	0.0135 (4)	−0.0005 (4)	0.0026 (3)	0.0002 (3)
C15	0.0224 (5)	0.0203 (4)	0.0176 (4)	−0.0035 (4)	0.0016 (4)	0.0031 (3)
C16	0.0211 (4)	0.0205 (4)	0.0174 (4)	−0.0057 (4)	0.0001 (3)	0.0005 (3)
C17	0.0334 (6)	0.0151 (4)	0.0219 (4)	−0.0044 (4)	0.0020 (4)	0.0017 (3)
C18	0.0312 (5)	0.0270 (5)	0.0147 (4)	−0.0029 (4)	0.0009 (4)	0.0066 (4)
C19	0.0366 (6)	0.0237 (5)	0.0228 (5)	−0.0125 (5)	0.0091 (4)	−0.0038 (4)
C20	0.0415 (7)	0.0325 (6)	0.0191 (5)	−0.0071 (5)	0.0013 (5)	0.0088 (4)

O1—C4	1.3562 (11)	C10—C11	1.4618 (12)
O1—C17	1.4247 (12)	C10—H10A	0.9300
O2—C5	1.3601 (11)	C11—C16	1.3968 (14)
O2—C18	1.4220 (12)	C11—C12	1.4072 (13)
O3—C8	1.2279 (12)	C12—C13	1.3862 (13)
O4—C13	1.3674 (12)	C12—H12A	0.9300
O4—C19	1.4197 (13)	C13—C14	1.4094 (14)
O5—C14	1.3667 (11)	C14—C15	1.3839 (14)
O5—C20	1.4273 (14)	C15—C16	1.3958 (13)
C1—C2	1.5084 (12)	C15—H15A	0.9300
C1—C9	1.5100 (14)	C16—H16A	0.9300
C1—H1A	0.9700	C17—H17A	0.9600
C1—H1B	0.9700	C17—H17B	0.9600
C2—C7	1.3832 (13)	C17—H17C	0.9600
C2—C3	1.3932 (13)	C18—H18A	0.9600
C3—C4	1.3909 (12)	C18—H18B	0.9600
C3—H3A	0.9300	C18—H18C	0.9600
C4—C5	1.4244 (13)	C19—H19A	0.9600
C5—C6	1.3781 (13)	C19—H19B	0.9600
C6—C7	1.4057 (12)	C19—H19C	0.9600
C6—H6A	0.9300	C20—H20A	0.9600
C7—C8	1.4703 (13)	C20—H20B	0.9600
C8—C9	1.4955 (12)	C20—H20C	0.9600
C9—C10	1.3497 (13)
C4—O1—C17	117.28 (7)	C13—C12—C11	120.88 (9)
C5—O2—C18	116.34 (8)	C13—C12—H12A	119.6
C13—O4—C19	117.15 (8)	C11—C12—H12A	119.6
C14—O5—C20	117.16 (8)	O4—C13—C12	125.03 (9)
C2—C1—C9	103.34 (7)	O4—C13—C14	114.56 (8)
C2—C1—H1A	111.1	C12—C13—C14	120.41 (9)
C9—C1—H1A	111.1	O5—C14—C15	125.21 (9)
C2—C1—H1B	111.1	O5—C14—C13	115.89 (9)
C9—C1—H1B	111.1	C15—C14—C13	118.89 (9)
H1A—C1—H1B	109.1	C14—C15—C16	120.63 (9)
C7—C2—C3	120.42 (8)	C14—C15—H15A	119.7
C7—C2—C1	111.71 (8)	C16—C15—H15A	119.7
C3—C2—C1	127.88 (8)	C15—C16—C11	121.08 (9)
C4—C3—C2	118.61 (8)	C15—C16—H16A	119.5
C4—C3—H3A	120.7	C11—C16—H16A	119.5
C2—C3—H3A	120.7	O1—C17—H17A	109.5
O1—C4—C3	124.94 (8)	O1—C17—H17B	109.5
O1—C4—C5	114.23 (8)	H17A—C17—H17B	109.5
C3—C4—C5	120.82 (8)	O1—C17—H17C	109.5
O2—C5—C6	125.87 (9)	H17A—C17—H17C	109.5
O2—C5—C4	114.07 (8)	H17B—C17—H17C	109.5
C6—C5—C4	120.05 (8)	O2—C18—H18A	109.5
C5—C6—C7	118.39 (9)	O2—C18—H18B	109.5
C5—C6—H6A	120.8	H18A—C18—H18B	109.5
C7—C6—H6A	120.8	O2—C18—H18C	109.5
C2—C7—C6	121.70 (9)	H18A—C18—H18C	109.5
C2—C7—C8	109.88 (8)	H18B—C18—H18C	109.5
C6—C7—C8	128.41 (9)	O4—C19—H19A	109.5
O3—C8—C7	126.65 (8)	O4—C19—H19B	109.5
O3—C8—C9	126.89 (9)	H19A—C19—H19B	109.5
C7—C8—C9	106.45 (8)	O4—C19—H19C	109.5
C10—C9—C8	121.23 (9)	H19A—C19—H19C	109.5
C10—C9—C1	130.15 (8)	H19B—C19—H19C	109.5
C8—C9—C1	108.62 (7)	O5—C20—H20A	109.5
C9—C10—C11	129.43 (9)	O5—C20—H20B	109.5
C9—C10—H10A	115.3	H20A—C20—H20B	109.5
C11—C10—H10A	115.3	O5—C20—H20C	109.5
C16—C11—C12	118.07 (8)	H20A—C20—H20C	109.5
C16—C11—C10	124.47 (8)	H20B—C20—H20C	109.5
C12—C11—C10	117.45 (9)
C9—C1—C2—C7	0.61 (11)	C7—C8—C9—C10	178.86 (9)
C9—C1—C2—C3	−179.23 (10)	O3—C8—C9—C1	−179.52 (10)
C7—C2—C3—C4	0.46 (15)	C7—C8—C9—C1	−0.30 (11)
C1—C2—C3—C4	−179.72 (9)	C2—C1—C9—C10	−179.22 (10)
C17—O1—C4—C3	−2.52 (15)	C2—C1—C9—C8	−0.16 (10)
C17—O1—C4—C5	178.15 (9)	C8—C9—C10—C11	−176.82 (10)
C2—C3—C4—O1	179.82 (9)	C1—C9—C10—C11	2.15 (18)
C2—C3—C4—C5	−0.89 (15)	C9—C10—C11—C16	−1.16 (17)
C18—O2—C5—C6	4.19 (15)	C9—C10—C11—C12	178.32 (10)
C18—O2—C5—C4	−176.80 (9)	C16—C11—C12—C13	0.89 (15)
O1—C4—C5—O2	0.83 (13)	C10—C11—C12—C13	−178.62 (9)
C3—C4—C5—O2	−178.53 (9)	C19—O4—C13—C12	5.66 (17)
O1—C4—C5—C6	179.91 (9)	C19—O4—C13—C14	−174.51 (10)
C3—C4—C5—C6	0.55 (15)	C11—C12—C13—O4	−179.43 (10)
O2—C5—C6—C7	179.19 (9)	C11—C12—C13—C14	0.74 (16)
C4—C5—C6—C7	0.23 (15)	C20—O5—C14—C15	0.73 (16)
C3—C2—C7—C6	0.33 (15)	C20—O5—C14—C13	−179.60 (10)
C1—C2—C7—C6	−179.52 (9)	O4—C13—C14—O5	−1.25 (14)
C3—C2—C7—C8	179.02 (9)	C12—C13—C14—O5	178.59 (10)
C1—C2—C7—C8	−0.83 (11)	O4—C13—C14—C15	178.44 (10)
C5—C6—C7—C2	−0.67 (15)	C12—C13—C14—C15	−1.72 (16)
C5—C6—C7—C8	−179.10 (10)	O5—C14—C15—C16	−179.29 (10)
C2—C7—C8—O3	179.92 (10)	C13—C14—C15—C16	1.05 (16)
C6—C7—C8—O3	−1.51 (18)	C14—C15—C16—C11	0.60 (17)
C2—C7—C8—C9	0.70 (11)	C12—C11—C16—C15	−1.57 (16)
C6—C7—C8—C9	179.27 (10)	C10—C11—C16—C15	177.91 (10)
O3—C8—C9—C10	−0.35 (17)

Cg1 is the cetroid of C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···O4i	0.96	2.34	3.0939 (13)	135
C1—H1A···Cg1ii	0.97	2.64	3.4804 (11)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the cetroid of C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18A⋯O4i	0.96	2.34	3.0939 (13)	135
C1—H1A⋯Cg1ii	0.97	2.64	3.4804 (11)	146

Symmetry codes: (i) ; (ii) .