2-(Di-phenyl-methyl-idene)-2,3-di-hydro-1H-inden-1-one.

In the title mol-ecule, C22H16O, the indanone ring system is approximately planar with a dihedral angle between the fused rings of 5.13 (14)°. Two benzene rings are linked together at one side of a double bond, sitting on either side of the indanone ring system and making dihedral angles of 70.30 (12) and 44.74 (13)° with it. In the crystal, hydrogen bonding is not present, but weak C-H⋯π or π-π inter-actions occur and mol-ecules form a sheet-like structure in the bc plane.

Related literature

For background to the indanone pharmacophore, its use as an organic inter­mediate and its biological activity, see: Buckle et al. (1973 ▶); Sheridan et al. (1990 ▶, 1999a ▶,b ▶, 2008 ▶, 2009a ▶,b ▶); Vacca et al. (1994 ▶); Schumann et al. (2001 ▶); Herzog et al. (2002 ▶); Frankish et al. (2004 ▶); Frankish & Sheridan (2012 ▶); Dinges et al. (2006 ▶); Kou et al. (2012 ▶); Ito et al. (2004 ▶); Jaki et al. (1999 ▶); Chanda et al. (2012 ▶); Chen et al. (2008 ▶); Rukachaisirikul et al. (2013 ▶); Farrell et al. (1996 ▶); Borbone et al. (2011 ▶); Fu & Wang (2008 ▶). For bond lengths and angles in related compounds, see: Ali et al. (2010a ▶,b ▶, 2011 ▶); Chen et al. (2011a ▶ 2011b ▶); Li et al. (2012 ▶); Lin et al. (2012 ▶).

Experimental

Crystal data

C22H16O

M = 296.35

Monoclinic,

a = 9.1634 (18) Å

b = 17.570 (3) Å

c = 10.717 (4) Å

β = 117.89 (2)°

V = 1525.0 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 150 K

0.50 × 0.20 × 0.20 mm

Data collection

Rigaku Saturn 724 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2006 ▶) T min = 0.763, T max = 1.000

11746 measured reflections

2680 independent reflections

2587 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.145

S = 1.25

2680 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrystalClear (Rigaku, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 and Mercury (Macrae et al., 2006 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813018990/gg2117sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018990/gg2117Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813018990/gg2117Isup3.cml

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

C22H16O	F(000) = 624
Mr = 296.35	Dx = 1.291 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5979 reflections
a = 9.1634 (18) Å	θ = 2.4–31.1°
b = 17.570 (3) Å	µ = 0.08 mm−1
c = 10.717 (4) Å	T = 150 K
β = 117.89 (2)°	Prism, colourless
V = 1525.0 (7) Å3	0.50 × 0.20 × 0.20 mm
Z = 4

Rigaku Saturn 724 diffractometer	2587 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.058
Graphite monochromator	θmax = 25.0°, θmin = 2.4°
ω and φ scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2006)	k = −20→13
Tmin = 0.763, Tmax = 1.000	l = −11→12
11746 measured reflections	4590 standard reflections every 120 reflections
2680 independent reflections	intensity decay: none

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.25	w = 1/[σ2(Fo2) + (0.0358P)2 + 1.5166P] where P = (Fo2 + 2Fc2)/3
2680 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.24 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
O1	0.3991 (2)	0.62562 (11)	0.58262 (19)	0.0266 (4)
C1	0.2609 (3)	0.69082 (14)	0.1518 (3)	0.0216 (6)
H1	0.1860	0.7305	0.1127	0.026*
C2	0.3856 (3)	0.68115 (15)	0.1133 (3)	0.0241 (6)
H2	0.3944	0.7148	0.0502	0.029*
C3	0.4960 (3)	0.62161 (15)	0.1689 (3)	0.0256 (6)
H3	0.5790	0.6151	0.1431	0.031*
C4	0.4829 (3)	0.57117 (16)	0.2640 (3)	0.0253 (6)
H4	0.5567	0.5309	0.3009	0.030*
C5	0.3595 (3)	0.58118 (15)	0.3035 (3)	0.0230 (6)
H5	0.3517	0.5475	0.3671	0.028*
C6	0.2469 (3)	0.64149 (14)	0.2488 (3)	0.0200 (5)
C7	0.1051 (3)	0.65032 (13)	0.2802 (3)	0.0192 (5)
C8	−0.0542 (3)	0.67304 (14)	0.1560 (3)	0.0195 (5)
C9	−0.1456 (3)	0.73524 (15)	0.1641 (3)	0.0244 (6)
H9	−0.1056	0.7638	0.2466	0.029*
C10	−0.2959 (3)	0.75445 (16)	0.0491 (3)	0.0306 (7)
H10	−0.3562	0.7956	0.0551	0.037*
C11	−0.3559 (3)	0.71206 (17)	−0.0747 (3)	0.0329 (7)
H11	−0.4570	0.7245	−0.1510	0.040*
C12	−0.2652 (3)	0.65121 (17)	−0.0848 (3)	0.0304 (7)
H12	−0.3054	0.6230	−0.1677	0.036*
C13	−0.1145 (3)	0.63269 (16)	0.0291 (3)	0.0255 (6)
H13	−0.0528	0.5928	0.0209	0.031*
C14	0.1063 (3)	0.63406 (14)	0.4049 (3)	0.0195 (5)
C15	−0.0506 (3)	0.62441 (15)	0.4193 (3)	0.0227 (6)
H15A	−0.1067	0.6728	0.4076	0.027*
H15B	−0.1256	0.5888	0.3498	0.027*
C16	0.0094 (3)	0.59403 (14)	0.5668 (3)	0.0208 (6)
C17	−0.0825 (3)	0.56906 (14)	0.6321 (3)	0.0239 (6)
H17	−0.1972	0.5682	0.5831	0.029*
C18	0.0010 (3)	0.54542 (15)	0.7717 (3)	0.0268 (6)
H18	−0.0591	0.5273	0.8153	0.032*
C19	0.1738 (4)	0.54814 (15)	0.8486 (3)	0.0278 (6)
H19	0.2266	0.5335	0.9429	0.033*
C20	0.2664 (3)	0.57288 (14)	0.7835 (3)	0.0250 (6)
H20	0.3810	0.5750	0.8332	0.030*
C21	0.1817 (3)	0.59445 (14)	0.6412 (3)	0.0209 (6)
C22	0.2509 (3)	0.61871 (14)	0.5466 (3)	0.0206 (6)

	U11	U22	U33	U12	U13	U23
O1	0.0225 (10)	0.0323 (11)	0.0230 (10)	−0.0011 (8)	0.0091 (8)	0.0002 (8)
C1	0.0214 (13)	0.0210 (13)	0.0214 (14)	−0.0001 (10)	0.0091 (11)	−0.0005 (10)
C2	0.0263 (14)	0.0235 (14)	0.0240 (15)	−0.0064 (11)	0.0130 (12)	−0.0018 (11)
C3	0.0200 (13)	0.0327 (15)	0.0256 (15)	−0.0035 (11)	0.0119 (12)	−0.0076 (12)
C4	0.0204 (13)	0.0296 (14)	0.0231 (15)	0.0028 (11)	0.0079 (12)	−0.0016 (11)
C5	0.0236 (13)	0.0230 (13)	0.0213 (14)	0.0013 (10)	0.0095 (12)	0.0026 (10)
C6	0.0197 (12)	0.0198 (12)	0.0184 (13)	−0.0034 (10)	0.0072 (11)	−0.0041 (10)
C7	0.0197 (13)	0.0159 (12)	0.0209 (14)	−0.0008 (10)	0.0087 (11)	−0.0019 (10)
C8	0.0191 (13)	0.0194 (12)	0.0206 (14)	−0.0003 (10)	0.0099 (11)	0.0045 (10)
C9	0.0246 (13)	0.0233 (13)	0.0289 (15)	0.0012 (11)	0.0155 (12)	0.0057 (11)
C10	0.0228 (14)	0.0286 (15)	0.0444 (19)	0.0074 (12)	0.0191 (14)	0.0168 (13)
C11	0.0203 (13)	0.0411 (17)	0.0319 (17)	0.0016 (12)	0.0077 (13)	0.0205 (14)
C12	0.0267 (15)	0.0394 (17)	0.0192 (15)	−0.0054 (12)	0.0059 (12)	0.0053 (12)
C13	0.0236 (14)	0.0301 (14)	0.0220 (15)	0.0011 (11)	0.0101 (12)	0.0041 (11)
C14	0.0211 (13)	0.0175 (12)	0.0201 (14)	−0.0005 (10)	0.0099 (11)	−0.0005 (10)
C15	0.0221 (13)	0.0251 (13)	0.0220 (14)	0.0017 (11)	0.0112 (11)	0.0021 (11)
C16	0.0280 (14)	0.0149 (12)	0.0205 (14)	−0.0005 (10)	0.0122 (12)	−0.0030 (10)
C17	0.0266 (14)	0.0209 (13)	0.0276 (15)	−0.0029 (11)	0.0156 (12)	−0.0037 (11)
C18	0.0378 (16)	0.0229 (13)	0.0257 (15)	−0.0037 (12)	0.0197 (13)	−0.0021 (11)
C19	0.0378 (16)	0.0260 (14)	0.0188 (14)	−0.0049 (12)	0.0125 (13)	−0.0010 (11)
C20	0.0280 (14)	0.0224 (13)	0.0219 (14)	−0.0072 (11)	0.0094 (12)	−0.0052 (11)
C21	0.0269 (14)	0.0158 (12)	0.0219 (14)	−0.0021 (10)	0.0130 (12)	−0.0033 (10)
C22	0.0233 (14)	0.0168 (12)	0.0229 (14)	−0.0011 (10)	0.0119 (12)	−0.0029 (10)

O1—C22	1.231 (3)	C11—C12	1.389 (4)
C1—C2	1.395 (3)	C11—H11	0.9300
C1—C6	1.405 (3)	C12—C13	1.388 (4)
C1—H1	0.9300	C12—H12	0.9300
C2—C3	1.382 (4)	C13—H13	0.9300
C2—H2	0.9300	C14—C22	1.501 (4)
C3—C4	1.397 (4)	C14—C15	1.525 (3)
C3—H3	0.9300	C15—C16	1.508 (3)
C4—C5	1.392 (4)	C15—H15A	0.9700
C4—H4	0.9300	C15—H15B	0.9700
C5—C6	1.402 (4)	C16—C17	1.393 (4)
C5—H5	0.9300	C16—C21	1.397 (4)
C6—C7	1.495 (3)	C17—C18	1.388 (4)
C7—C14	1.362 (4)	C17—H17	0.9300
C7—C8	1.498 (3)	C18—C19	1.403 (4)
C8—C13	1.398 (4)	C18—H18	0.9300
C8—C9	1.404 (4)	C19—C20	1.396 (4)
C9—C10	1.394 (4)	C19—H19	0.9300
C9—H9	0.9300	C20—C21	1.402 (4)
C10—C11	1.391 (4)	C20—H20	0.9300
C10—H10	0.9300	C21—C22	1.488 (3)
C2—C1—C6	121.0 (2)	C11—C12—H12	120.1
C2—C1—H1	119.5	C12—C13—C8	121.0 (3)
C6—C1—H1	119.5	C12—C13—H13	119.5
C3—C2—C1	120.0 (2)	C8—C13—H13	119.5
C3—C2—H2	120.0	C7—C14—C22	128.9 (2)
C1—C2—H2	120.0	C7—C14—C15	123.2 (2)
C2—C3—C4	120.0 (2)	C22—C14—C15	107.8 (2)
C2—C3—H3	120.0	C16—C15—C14	104.3 (2)
C4—C3—H3	120.0	C16—C15—H15A	110.9
C5—C4—C3	120.1 (2)	C14—C15—H15A	110.9
C5—C4—H4	120.0	C16—C15—H15B	110.9
C3—C4—H4	120.0	C14—C15—H15B	110.9
C4—C5—C6	120.8 (2)	H15A—C15—H15B	108.9
C4—C5—H5	119.6	C17—C16—C21	120.1 (2)
C6—C5—H5	119.6	C17—C16—C15	128.9 (2)
C5—C6—C1	118.1 (2)	C21—C16—C15	110.9 (2)
C5—C6—C7	122.1 (2)	C18—C17—C16	118.6 (2)
C1—C6—C7	119.5 (2)	C18—C17—H17	120.7
C14—C7—C6	126.2 (2)	C16—C17—H17	120.7
C14—C7—C8	119.0 (2)	C17—C18—C19	121.6 (2)
C6—C7—C8	114.6 (2)	C17—C18—H18	119.2
C13—C8—C9	118.6 (2)	C19—C18—H18	119.2
C13—C8—C7	120.4 (2)	C20—C19—C18	120.0 (3)
C9—C8—C7	121.0 (2)	C20—C19—H19	120.0
C10—C9—C8	120.4 (3)	C18—C19—H19	120.0
C10—C9—H9	119.8	C19—C20—C21	118.1 (2)
C8—C9—H9	119.8	C19—C20—H20	120.9
C11—C10—C9	120.0 (3)	C21—C20—H20	120.9
C11—C10—H10	120.0	C16—C21—C20	121.5 (2)
C9—C10—H10	120.0	C16—C21—C22	109.9 (2)
C12—C11—C10	120.2 (3)	C20—C21—C22	128.6 (2)
C12—C11—H11	119.9	O1—C22—C21	125.0 (2)
C10—C11—H11	119.9	O1—C22—C14	128.5 (2)
C13—C12—C11	119.8 (3)	C21—C22—C14	106.5 (2)
C13—C12—H12	120.1
C6—C1—C2—C3	1.1 (4)	C6—C7—C14—C15	−163.5 (2)
C1—C2—C3—C4	−0.1 (4)	C8—C7—C14—C15	10.9 (4)
C2—C3—C4—C5	−0.5 (4)	C7—C14—C15—C16	170.5 (2)
C3—C4—C5—C6	0.2 (4)	C22—C14—C15—C16	−6.8 (3)
C4—C5—C6—C1	0.7 (4)	C14—C15—C16—C17	−174.2 (2)
C4—C5—C6—C7	175.1 (2)	C14—C15—C16—C21	7.2 (3)
C2—C1—C6—C5	−1.4 (4)	C21—C16—C17—C18	0.5 (4)
C2—C1—C6—C7	−175.9 (2)	C15—C16—C17—C18	−178.1 (2)
C5—C6—C7—C14	36.5 (4)	C16—C17—C18—C19	1.8 (4)
C1—C6—C7—C14	−149.2 (3)	C17—C18—C19—C20	−2.0 (4)
C5—C6—C7—C8	−138.0 (2)	C18—C19—C20—C21	0.0 (4)
C1—C6—C7—C8	36.2 (3)	C17—C16—C21—C20	−2.5 (4)
C14—C7—C8—C13	−123.9 (3)	C15—C16—C21—C20	176.3 (2)
C6—C7—C8—C13	51.1 (3)	C17—C16—C21—C22	176.4 (2)
C14—C7—C8—C9	56.4 (3)	C15—C16—C21—C22	−4.8 (3)
C6—C7—C8—C9	−128.6 (2)	C19—C20—C21—C16	2.2 (4)
C13—C8—C9—C10	2.1 (4)	C19—C20—C21—C22	−176.5 (2)
C7—C8—C9—C10	−178.2 (2)	C16—C21—C22—O1	178.9 (2)
C8—C9—C10—C11	−0.2 (4)	C20—C21—C22—O1	−2.2 (4)
C9—C10—C11—C12	−0.9 (4)	C16—C21—C22—C14	0.2 (3)
C10—C11—C12—C13	0.1 (4)	C20—C21—C22—C14	179.1 (2)
C11—C12—C13—C8	1.9 (4)	C7—C14—C22—O1	8.6 (4)
C9—C8—C13—C12	−2.9 (4)	C15—C14—C22—O1	−174.4 (2)
C7—C8—C13—C12	177.3 (2)	C7—C14—C22—C21	−172.8 (2)
C6—C7—C14—C22	13.2 (4)	C15—C14—C22—C21	4.2 (3)
C8—C7—C14—C22	−172.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cg1i	0.93	2.91	3.763 (3)	153
C11—H11···Cg2ii	0.93	2.99	3.712 (3)	136
C15—H15B···Cg4iii	0.97	2.92	3.640 (3)	132

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg4 are the centroids of the C14–C16/C21/C22, C1–C6 and C16–C21 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cg1i	0.93	2.91	3.763 (3)	153
C11—H11⋯Cg2ii	0.93	2.99	3.712 (3)	136
C15—H15B⋯Cg4iii	0.97	2.92	3.640 (3)	132

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