(2E)-2-Benzyl-idene-5,6-dimethoxy-indan-1-one.

The mol-ecular structure of the title compound, C(18)H(16)O(3), is roughly planar; the maximum deviation of the indanone ring system is 0.027 (1) Å and it makes a dihedral angle of 2.69 (3)° with the phenyl ring. The torsion angles between the two meth-oxy groups and the -indanone ring are -14.67 (11) and -1.11 (12)°. In the crystal, mol-ecules are connected into a ribbon along the a axis via weak inter-molecular C-H⋯O hydrogen bonds. Weak inter-molecular C-H⋯π and π-π [centroid-centroid distance = 3.7086 (6) Å] inter-actions are also observed.

Related literature

For general background to and the biological activity of chalcone derivatives, see: Boumendjel et al. (2009 ▶); D’Archivio et al. (2008 ▶); Dicarlo et al. (1999 ▶); Echeverria et al. (2009 ▶); Heidenreich et al. (2008 ▶); Katsori & Hadjipavlou-Latina (2009 ▶); Miranda et al. (1999 ▶); Nowakowska (2007 ▶); Shah et al. (2008 ▶); Syed et al. (2008 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C18H16O3

M = 280.31

Monoclinic,

a = 6.0209 (6) Å

b = 14.8550 (14) Å

c = 15.2292 (15) Å

β = 90.603 (2)°

V = 1362.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.44 × 0.29 × 0.16 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.960, T max = 0.985

31475 measured reflections

6003 independent reflections

4902 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.130

S = 1.09

6003 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.58 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/S1600536810035695/is2598sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035695/is2598Isup2.hkl

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

C18H16O3	F(000) = 592
Mr = 280.31	Dx = 1.367 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7296 reflections
a = 6.0209 (6) Å	θ = 2.7–34.9°
b = 14.8550 (14) Å	µ = 0.09 mm−1
c = 15.2292 (15) Å	T = 100 K
β = 90.603 (2)°	Yellow, colourless
V = 1362.0 (2) Å3	0.44 × 0.29 × 0.16 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	6003 independent reflections
Radiation source: fine-focus sealed tube	4902 reflections with I > 2σ(I)
graphite	Rint = 0.048
φ and ω scans	θmax = 35.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.960, Tmax = 0.985	k = −23→23
31475 measured reflections	l = −23→24

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) = 0.130	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0698P)2 + 0.2363P] where P = (Fo2 + 2Fc2)/3
6003 reflections	(Δ/σ)max = 0.001
192 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.58 e Å−3

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
O1	0.07043 (10)	0.71482 (4)	0.09037 (4)	0.01685 (13)
O2	0.07512 (10)	0.55593 (4)	0.41523 (4)	0.01527 (12)
O3	0.42675 (10)	0.46101 (4)	0.40716 (4)	0.01623 (13)
C1	0.22764 (13)	0.66575 (5)	0.11035 (5)	0.01189 (13)
C2	0.26214 (13)	0.61731 (5)	0.19344 (5)	0.01122 (13)
C3	0.12486 (13)	0.61613 (5)	0.26768 (5)	0.01208 (13)
H3A	−0.0055	0.6497	0.2689	0.014*
C4	0.18842 (13)	0.56395 (5)	0.33862 (5)	0.01188 (13)
C5	0.38768 (13)	0.51154 (5)	0.33496 (5)	0.01213 (13)
C6	0.52425 (13)	0.51522 (5)	0.26166 (5)	0.01263 (14)
H6A	0.6561	0.4827	0.2602	0.015*
C7	0.45911 (12)	0.56873 (5)	0.19043 (5)	0.01121 (13)
C8	0.57760 (13)	0.58179 (5)	0.10412 (5)	0.01231 (13)
H8A	0.5966	0.5249	0.0738	0.015*
H8B	0.7219	0.6095	0.1131	0.015*
C9	0.42250 (13)	0.64368 (5)	0.05349 (5)	0.01186 (13)
C10	0.43407 (13)	0.67809 (5)	−0.02828 (5)	0.01274 (14)
H10A	0.3154	0.7150	−0.0441	0.015*
C11	0.60191 (13)	0.66724 (5)	−0.09638 (5)	0.01229 (13)
C12	0.79718 (14)	0.61621 (6)	−0.08618 (5)	0.01469 (14)
H12A	0.8259	0.5868	−0.0334	0.018*
C13	0.94801 (14)	0.60945 (6)	−0.15463 (6)	0.01690 (15)
H13A	1.0760	0.5751	−0.1472	0.020*
C14	0.90917 (15)	0.65353 (6)	−0.23413 (6)	0.01682 (15)
H14A	1.0106	0.6487	−0.2795	0.020*
C15	0.71743 (15)	0.70489 (6)	−0.24506 (6)	0.01576 (15)
H15A	0.6910	0.7349	−0.2977	0.019*
C16	0.56526 (14)	0.71135 (5)	−0.17716 (5)	0.01416 (14)
H16A	0.4370	0.7454	−0.1853	0.017*
C17	−0.09525 (14)	0.62140 (6)	0.43137 (6)	0.01619 (15)
H17A	−0.1545	0.6122	0.4890	0.024*
H17B	−0.2118	0.6149	0.3883	0.024*
H17C	−0.0333	0.6808	0.4276	0.024*
C18	0.62128 (14)	0.40534 (6)	0.40883 (6)	0.01640 (15)
H18A	0.6235	0.3701	0.4617	0.025*
H18B	0.7514	0.4426	0.4071	0.025*
H18C	0.6192	0.3660	0.3588	0.025*

	U11	U22	U33	U12	U13	U23
O1	0.0151 (3)	0.0202 (3)	0.0153 (3)	0.0057 (2)	0.0018 (2)	0.0026 (2)
O2	0.0144 (3)	0.0191 (3)	0.0123 (3)	0.0035 (2)	0.0052 (2)	0.0029 (2)
O3	0.0157 (3)	0.0197 (3)	0.0133 (3)	0.0048 (2)	0.0024 (2)	0.0056 (2)
C1	0.0121 (3)	0.0125 (3)	0.0111 (3)	0.0000 (2)	0.0014 (2)	−0.0003 (2)
C2	0.0117 (3)	0.0116 (3)	0.0104 (3)	−0.0001 (2)	0.0013 (2)	0.0003 (2)
C3	0.0116 (3)	0.0128 (3)	0.0119 (3)	0.0004 (2)	0.0017 (2)	0.0001 (2)
C4	0.0109 (3)	0.0137 (3)	0.0111 (3)	−0.0003 (2)	0.0024 (2)	0.0000 (2)
C5	0.0122 (3)	0.0126 (3)	0.0116 (3)	0.0001 (2)	0.0005 (2)	0.0014 (2)
C6	0.0116 (3)	0.0143 (3)	0.0120 (3)	0.0013 (2)	0.0012 (2)	0.0009 (2)
C7	0.0112 (3)	0.0114 (3)	0.0110 (3)	−0.0005 (2)	0.0013 (2)	−0.0001 (2)
C8	0.0118 (3)	0.0140 (3)	0.0111 (3)	0.0013 (2)	0.0021 (2)	0.0007 (2)
C9	0.0118 (3)	0.0124 (3)	0.0115 (3)	0.0005 (2)	0.0019 (2)	0.0000 (2)
C10	0.0134 (3)	0.0130 (3)	0.0118 (3)	0.0010 (2)	0.0015 (2)	0.0003 (2)
C11	0.0136 (3)	0.0120 (3)	0.0113 (3)	−0.0004 (2)	0.0015 (2)	0.0002 (2)
C12	0.0143 (3)	0.0165 (3)	0.0133 (3)	0.0018 (3)	0.0019 (3)	0.0014 (3)
C13	0.0148 (3)	0.0193 (4)	0.0167 (4)	0.0021 (3)	0.0038 (3)	−0.0005 (3)
C14	0.0175 (4)	0.0185 (4)	0.0146 (3)	−0.0029 (3)	0.0057 (3)	−0.0015 (3)
C15	0.0186 (4)	0.0164 (3)	0.0123 (3)	−0.0030 (3)	0.0024 (3)	0.0015 (3)
C16	0.0154 (3)	0.0145 (3)	0.0126 (3)	0.0003 (2)	0.0012 (3)	0.0013 (2)
C17	0.0141 (3)	0.0189 (4)	0.0156 (3)	0.0024 (3)	0.0043 (3)	−0.0007 (3)
C18	0.0153 (3)	0.0169 (3)	0.0171 (4)	0.0032 (3)	−0.0010 (3)	0.0032 (3)

O1—C1	1.2303 (10)	C10—C11	1.4645 (11)
O2—C4	1.3628 (10)	C10—H10A	0.9300
O2—C17	1.4366 (10)	C11—C12	1.4061 (11)
O3—C5	1.3499 (10)	C11—C16	1.4092 (11)
O3—C18	1.4338 (10)	C12—C13	1.3933 (12)
C1—C2	1.4687 (11)	C12—H12A	0.9300
C1—C9	1.5017 (11)	C13—C14	1.3941 (12)
C2—C7	1.3894 (11)	C13—H13A	0.9300
C2—C3	1.4076 (11)	C14—C15	1.3923 (13)
C3—C4	1.3805 (11)	C14—H14A	0.9300
C3—H3A	0.9300	C15—C16	1.3920 (12)
C4—C5	1.4318 (11)	C15—H15A	0.9300
C5—C6	1.3945 (11)	C16—H16A	0.9300
C6—C7	1.3977 (11)	C17—H17A	0.9600
C6—H6A	0.9300	C17—H17B	0.9600
C7—C8	1.5146 (11)	C17—H17C	0.9600
C8—C9	1.5154 (11)	C18—H18A	0.9600
C8—H8A	0.9700	C18—H18B	0.9600
C8—H8B	0.9700	C18—H18C	0.9600
C9—C10	1.3487 (11)
C4—O2—C17	116.88 (6)	C9—C10—H10A	114.5
C5—O3—C18	118.07 (7)	C11—C10—H10A	114.5
O1—C1—C2	127.21 (7)	C12—C11—C16	118.04 (7)
O1—C1—C9	126.20 (7)	C12—C11—C10	124.30 (7)
C2—C1—C9	106.59 (6)	C16—C11—C10	117.65 (7)
C7—C2—C3	121.92 (7)	C13—C12—C11	120.47 (8)
C7—C2—C1	109.82 (7)	C13—C12—H12A	119.8
C3—C2—C1	128.26 (7)	C11—C12—H12A	119.8
C4—C3—C2	118.38 (7)	C12—C13—C14	120.74 (8)
C4—C3—H3A	120.8	C12—C13—H13A	119.6
C2—C3—H3A	120.8	C14—C13—H13A	119.6
O2—C4—C3	125.58 (7)	C15—C14—C13	119.50 (8)
O2—C4—C5	114.40 (7)	C15—C14—H14A	120.2
C3—C4—C5	120.02 (7)	C13—C14—H14A	120.2
O3—C5—C6	125.08 (7)	C16—C15—C14	120.02 (8)
O3—C5—C4	114.17 (7)	C16—C15—H15A	120.0
C6—C5—C4	120.75 (7)	C14—C15—H15A	120.0
C5—C6—C7	118.72 (7)	C15—C16—C11	121.21 (8)
C5—C6—H6A	120.6	C15—C16—H16A	119.4
C7—C6—H6A	120.6	C11—C16—H16A	119.4
C2—C7—C6	120.16 (7)	O2—C17—H17A	109.5
C2—C7—C8	111.85 (7)	O2—C17—H17B	109.5
C6—C7—C8	127.99 (7)	H17A—C17—H17B	109.5
C7—C8—C9	103.06 (6)	O2—C17—H17C	109.5
C7—C8—H8A	111.2	H17A—C17—H17C	109.5
C9—C8—H8A	111.2	H17B—C17—H17C	109.5
C7—C8—H8B	111.2	O3—C18—H18A	109.5
C9—C8—H8B	111.2	O3—C18—H18B	109.5
H8A—C8—H8B	109.1	H18A—C18—H18B	109.5
C10—C9—C1	119.86 (7)	O3—C18—H18C	109.5
C10—C9—C8	131.47 (7)	H18A—C18—H18C	109.5
C1—C9—C8	108.67 (6)	H18B—C18—H18C	109.5
C9—C10—C11	130.91 (7)
O1—C1—C2—C7	179.73 (8)	C5—C6—C7—C2	0.24 (11)
C9—C1—C2—C7	−0.12 (8)	C5—C6—C7—C8	−178.92 (7)
O1—C1—C2—C3	0.09 (13)	C2—C7—C8—C9	−1.30 (8)
C9—C1—C2—C3	−179.76 (7)	C6—C7—C8—C9	177.91 (8)
C7—C2—C3—C4	−0.86 (11)	O1—C1—C9—C10	−0.86 (13)
C1—C2—C3—C4	178.74 (7)	C2—C1—C9—C10	179.00 (7)
C17—O2—C4—C3	−14.67 (11)	O1—C1—C9—C8	179.44 (8)
C17—O2—C4—C5	165.99 (7)	C2—C1—C9—C8	−0.71 (8)
C2—C3—C4—O2	179.62 (7)	C7—C8—C9—C10	−178.48 (8)
C2—C3—C4—C5	−1.07 (11)	C7—C8—C9—C1	1.18 (8)
C18—O3—C5—C6	−1.11 (12)	C1—C9—C10—C11	−179.66 (8)
C18—O3—C5—C4	179.19 (7)	C8—C9—C10—C11	−0.03 (15)
O2—C4—C5—O3	1.72 (10)	C9—C10—C11—C12	−1.40 (14)
C3—C4—C5—O3	−177.66 (7)	C9—C10—C11—C16	178.97 (8)
O2—C4—C5—C6	−178.00 (7)	C16—C11—C12—C13	−0.44 (12)
C3—C4—C5—C6	2.62 (12)	C10—C11—C12—C13	179.93 (8)
O3—C5—C6—C7	178.15 (7)	C11—C12—C13—C14	0.46 (13)
C4—C5—C6—C7	−2.16 (12)	C12—C13—C14—C15	0.04 (13)
C3—C2—C7—C6	1.31 (11)	C13—C14—C15—C16	−0.54 (13)
C1—C2—C7—C6	−178.36 (7)	C14—C15—C16—C11	0.55 (12)
C3—C2—C7—C8	−179.41 (7)	C12—C11—C16—C15	−0.06 (12)
C1—C2—C7—C8	0.92 (9)	C10—C11—C16—C15	179.60 (7)

Cg1 is the centroid of C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···O3i	0.96	2.53	3.4107 (11)	152
C18—H18B···O2ii	0.96	2.58	3.5320 (11)	173
C16—H16A···Cg1iii	0.93	2.99	3.7224 (9)	137

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯O3i	0.96	2.53	3.4107 (11)	152
C18—H18B⋯O2ii	0.96	2.58	3.5320 (11)	173
C16—H16A⋯Cg1iii	0.93	2.99	3.7224 (9)	137

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