2-(Di­phenyl­methyl­idene)-2,3-di­hydro-1H-inden-1-one

Zhang, T.; Bandero, V.; McCabe, T.; Frankish, N.; Sheridan, H.

doi:10.1107/S1600536813018990

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Pages o1306-o1307

doi:10.1107/S1600536813018990

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2-(Diphenylmethylidene)-2,3-dihydro-1H-inden-1-one

Tao Zhang,^a Vilmar Bandero,^a Tom McCabe,^b Neil Frankish ^a and Helen Sheridan ^a ^*

^aDrug Discovery Group, School of Pharmacy and Pharmaceutical Sciences, Trinity College Dublin, Dublin 2, Ireland, and ^bSchool of Chemistry, Trinity College Dublin, Dublin 2, Ireland
^*Correspondence e-mail: hsheridn@tcd.ie

(Received 10 June 2013; accepted 9 July 2013; online 24 July 2013)

In the title molecule, 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 interactions occur and molecules 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_r = 296.35
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.070
wR(F²) = 0.145
S = 1.25
2680 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x, -y+1, -z+1.

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).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813018990/gg2117sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813018990/gg2117Isup3.cml

checkCIF report

Comment top

The indanone scaffold has been widely observed in the natural world (Jaki et al., 1999; Ito et al., 2004; Chen et al., 2008; Chanda et al., 2012; Rukachaisirikul et al., 2013). As organic intermediates, many indanone derivatives are used during chemical synthesis (Sheridan et al., 1990; Farrell et al., 1996; Sheridan et al., 1999a,b; Frankish et al., 2004; Borbone et al., 2011; Fu & Wang, 2008). Many studies show indanone pharmacophore is associated with a wide variety of biological properties such as: KDR kinase inhibition, mast cell stabilization, smooth muscle relaxation, antioxidation, and is used to target diseases such as cancer and Alzheimer's disease (Schumann et al., 2001; Herzog et al., 2002; Dinges et al., 2006; Sheridan et al., 2009a,b; Kou et al., 2012).

The asymmetric unit of the title molecule (I) is shown in Figure 1. It crystallizes in the non-chiral, monoclinic space group P2₁/c. The two benzene rings, C8—C13 and C1—C6 in the molecule lie above and below the C16—C21 plane, with the dihedral angles 70.30 (12)° and 44.74 (13)°, respectively. The torsion angles of these two benzene groups are [C14—C7—C8—C9] = 56.4 (3)° and [C14—C7—C6—C5] = 36.5 (4)°. The rest of the molecule is essentially planar. The indanone fraction shows the normal values for this type of molecules (Ali et al., 2010a,b; Ali et al., 2011; Chen et al., 2011a,b; Li et al., 2012; Lin et al., 2012), with the C20—C21—C16—C15 bond angle being 176.3 (2)° and the bond length of benzylic carbonyl functionality (C22—O1) 1.231 (3) Å. The double bond (C14=C7) is located at alpha position to the carbonyl group of the indanone ring, with the bond length being 1.362 (4) Å. The geometry around quaternary C7 can be considered as a planar triangle: C14—C7—C8 = 119.0 (2)°, C14—C7—C6 = 126.2 (3)° and C6—C7—C8 = 114.6 (2)°. The packing diagrams of the molecular structure are presented in Figure 2. Weak intermolecular C—H···π and π-π interactions are observed in Figure 2a, which seems to be very effective in the stabilization of the crystal structure. Figure 2b shows that the molecules are separated by forming a sheet-like structure in the bc-plane when viewed along the crystallographic b-axis. It is suggested that weak Van der Vaals force or electrostatic interaction could be contributed to the linkage of the sheets.

Related literature top

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 top

To a stirred solution of 2-((2-hydroxyethoxy)diphenylmethyl)-2,3-dihydroinden-1-one (2.23 mmol) in methanol/DCM (12 ml, v:v, 3:1) was added trifluoromethanesulfonic acid (0.2 ml). The reaction was stirred at reflux for one hour, after which time the reaction was quenched by the addition of 2M NaOH aq. solution (20 ml) and the product was extracted with DCM (3 x 25 ml). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo, and the residue was purified by flash column chromatography on silica gel 230–400mesh (eluent: hexane: ethyl acetate, 10:1). All homogenous fractions were collected and the solvent removed in vacuo to afford titled crossed aldol condensed compound (94%) as yellow solid. Crystals suitable for X-ray diffraction were obtained after 7 days of slow evaporation of an ethyl acetate solution.

Computing details top

Data collection: CrystalClear (Rigaku, 2006); cell refinement: CrystalClear (Rigaku, 2006); data reduction: CrystalClear (Rigaku, 2006); 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 (Sheldrick, 2008) and Mercury (Macrae et al., 2006).

Figures top

	Fig. 1. The molecule structure of the titled compound with the atom numbering scheme. Displacement ellipsoids are shown at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. a. The molecular packing, viewed along the a axis.
	Fig. 3. b. The molecular packing, viewed along the b axis.

2-(Diphenylmethylidene)-2,3-dihydro-1H-inden-1-one top

Crystal data top

C₂₂H₁₆O	F(000) = 624
M_r = 296.35	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0358P)² + 1.5166P] where P = (F_o² + 2F_c²)/3
2680 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₂H₁₆O	V = 1525.0 (7) Å³
M_r = 296.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.1634 (18) Å	µ = 0.08 mm⁻¹
b = 17.570 (3) Å	T = 150 K
c = 10.717 (4) Å	0.50 × 0.20 × 0.20 mm
β = 117.89 (2)°

Data collection top

Rigaku Saturn 724 diffractometer	2587 reflections with I > 2σ(I)
Absorption correction: multi-scan (CrystalClear; Rigaku, 2006)	R_int = 0.058
T_min = 0.763, T_max = 1.000	4590 standard reflections every 120 reflections
11746 measured reflections	intensity decay: none
2680 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.25	Δρ_max = 0.19 e Å⁻³
2680 reflections	Δρ_min = −0.24 e Å⁻³
209 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+3/2, z−1/2; (ii) x−1, −y+3/2, z−1/2; (iii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₆O
M_r	296.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	9.1634 (18), 17.570 (3), 10.717 (4)
β (°)	117.89 (2)
V (Å³)	1525.0 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku Saturn 724 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2006)
T_min, T_max	0.763, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11746, 2680, 2587
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.145, 1.25
No. of reflections	2680
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.24

Computer programs: CrystalClear (Rigaku, 2006), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006), SHELXL97 (Sheldrick, 2008) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

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) x, −y+3/2, z−1/2; (ii) x−1, −y+3/2, z−1/2; (iii) −x, −y+1, −z+1.

Acknowledgements

We wish to thank Trinity College Dublin for financial support, Trinity College Postgraduate Research Studentships.

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Volume 69| Part 8| August 2013| Pages o1306-o1307

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