11-Hy­droxy-9-(prop-2-en-1-yl)-9,10-dihydro-9,10-propano­anthracen-12-one

Karama, U.; Almansour, A.I.; Arumugam, N.; Razak, I.A.; Arshad, S.

doi:10.1107/S1600536811033538

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2487

doi:10.1107/S1600536811033538

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11-Hydroxy-9-(prop-2-en-1-yl)-9,10-dihydro-9,10-propanoanthracen-12-one

Usama Karama,^a Abdulrahman I. Almansour,^a Natarajan Arumugam,^a Ibrahim Abdul Razak ^b ^*‡ and Suhana Arshad ^b

^aDepartment of Chemistry, College of Sciences, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia, and ^bSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: arazaki@usm.my

(Received 11 August 2011; accepted 17 August 2011; online 27 August 2011)

In the title compound, C₂₀H₁₈O₂, the central six-membered ring adopts a boat conformation and the terminal benzene rings make a dihedral angle of 42.66 (4)° with each other. In the crystal structure, the O—H group forms both an intra- and an intermolecular O—H⋯O hydrogen bond; the former generates an S(5) ring and the latter leads to inversion-generated R₂²(10) loops. The dimers are further linked into ribbons propagating along the a axis by C—H⋯O interactions, and the packing is consolidated by weak C—H⋯π interactions.

Related literature

For background to benzoctamine, see: Wilhelm & Schmidt (1969 ); Karama et al. (2010a ). For further synthetic details, see: Karama et al. (2010b ). For ring conformations, see: Cremer & Pople (1975 ). For bond-length data, see: Allen et al. (1987 ). For graph-set descriptors of hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₁₈O₂
M_r = 290.34
Triclinic, $[P \overline 1]$
a = 7.60940 (1) Å
b = 9.16090 (1) Å
c = 11.1735 (2) Å
α = 84.202 (1)°
β = 85.707 (1)°
γ = 69.895 (1)°
V = 727.02 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.57 × 0.39 × 0.27 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.954, T_max = 0.978
14851 measured reflections
5283 independent reflections
4634 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.130
S = 1.06
5283 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1	0.948 (18)	2.08 (2)	2.600 (2)	113 (2)
O2—H1O2⋯O1ⁱ	0.948 (18)	2.01 (2)	2.8041 (10)	140 (2)
C14—H14A⋯O2ⁱⁱ	1.00	2.41	3.3909 (12)	166
C17—H17A⋯Cg1ⁱⁱⁱ	1.00	2.92	3.6542 (10)	131
C20—H20A⋯Cg1^iv	0.95	2.79	3.6357 (11)	149
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x+1, y, z; (iii) -x+1, -y+2, -z; (iv) -x+1, -y+2, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811033538/hb6360sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033538/hb6360Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811033538/hb6360Isup3.cml

checkCIF report

Comment top

Benzoctamine is a clinically useful drug for the treatment of anxiety (Wilhelm & Schmidt, 1969) and our research group recently reported (Karama et al., 2010a) the synthesis of bishomobenzoctamine (Karama et al., 2010b) as it is a structural mimic of benzoctamine and was derived from anthrone which might be exhibited antidepressant activity. The title compound is the key intermediate for the synthesis of bishomobenzoctamine and its crystal structure is presented here.

In the molecular structure (Fig 1), the central 6-membered ring (C1/C6–C8/C13/C14) adopts a boat conformation with puckering amplitude Q = 0.6082 (9) Å, θ = 91.42 (8)° and ϕ = 120.69 (9)° (Cremer & Pople, 1975). The terminal benzene rings (C1–C6 and C8–C13) make a dihedral angle of 42.66 (4)° to each other. The bond lengths (Allen et al., 1987) and angles are within normal ranges.

The crystal packing is shown in Fig. 2. The molecules are linked by the intermolecular O2—H1O2···O1 hydrogen bonds (Table 1) and generating R²₂(10) ring motifs (Bernstein et al., 1995). These ring motifs are further linked into ribbons along a axis via intermolecular C14—H14A···O2 hydrogen bonds (Table 1). In addition, the C—H···π interactions (Table 1) which involves C17 and C20 with the phenyl ring (Cg1; C1–C6) further stabilized the structure.

Related literature top

For background to benzoctamine, see: Wilhelm & Schmidt (1969); Karama et al. (2010a). For further synthetic details, see: Karama et al. (2010b). For ring conformations, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987). For graph-set descriptors of hydrogen-bond motifs, see: Bernstein et al. (1995). For the operation of the cryostat, see: Cosier & Glazer (1986).

Experimental top

To 12-Bromo-9-(prop-2-en-1-yl)-9,10-dihydro-9,10-ethanoanthracen-12-carbaldehyde (Karama et al., 2010a) (1 g, 2.85 mmol) in THF (10 ml) was added 1M aqueous NaOH (10 ml). The mixture was stirred at room temperature for 4 h, extracted with ether twice, washed with water, dried with MgSO₄ and the solvent was evaporated in vacuo to yield the crude product. The crude product was purified by column chromatography on silica gel (petroleum ether–ethyl acetate 5:1) and product was crystallized from EtOAc to reveal the title compound as colourless blocks.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. Dashed lines represent the intermolecular hydrogen bonds.

15-hydroxy-1-(prop-2-en-1-yl)tetracyclo[6.6.3.0^2,7.0^9,14]heptadeca- 2,4,6,9(14),10,12-hexaen-16-one top

Crystal data top

C₂₀H₁₈O₂	Z = 2
M_r = 290.34	F(000) = 308
Triclinic, P1	D_x = 1.326 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.60940 (1) Å	Cell parameters from 7628 reflections
b = 9.16090 (1) Å	θ = 2.4–32.6°
c = 11.1735 (2) Å	µ = 0.08 mm⁻¹
α = 84.202 (1)°	T = 100 K
β = 85.707 (1)°	Block, colourless
γ = 69.895 (1)°	0.57 × 0.39 × 0.27 mm
V = 727.02 (2) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	5283 independent reflections
Radiation source: fine-focus sealed tube	4634 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 32.7°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.954, T_max = 0.978	k = −13→13
14851 measured reflections	l = −16→15

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.073P)² + 0.1953P] where P = (F_o² + 2F_c²)/3
5283 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₀H₁₈O₂	γ = 69.895 (1)°
M_r = 290.34	V = 727.02 (2) Å³
Triclinic, P1	Z = 2
a = 7.60940 (1) Å	Mo Kα radiation
b = 9.16090 (1) Å	µ = 0.08 mm⁻¹
c = 11.1735 (2) Å	T = 100 K
α = 84.202 (1)°	0.57 × 0.39 × 0.27 mm
β = 85.707 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	5283 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4634 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.978	R_int = 0.022
14851 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.59 e Å⁻³
5283 reflections	Δρ_min = −0.26 e Å⁻³
203 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.68817 (9)	0.54934 (8)	−0.00032 (6)	0.01745 (14)
O2	0.37722 (10)	0.68003 (9)	0.12072 (7)	0.01983 (15)
C1	0.78621 (12)	0.92873 (9)	0.16802 (8)	0.01291 (15)
C2	0.85293 (13)	1.05379 (10)	0.15089 (8)	0.01569 (16)
H2A	0.9775	1.0374	0.1203	0.019*
C3	0.73774 (14)	1.20262 (10)	0.17841 (9)	0.01855 (17)
H3A	0.7840	1.2873	0.1686	0.022*
C4	0.55436 (14)	1.22547 (10)	0.22043 (9)	0.01800 (17)
H4A	0.4745	1.3268	0.2383	0.022*
C5	0.48627 (12)	1.10130 (10)	0.23671 (8)	0.01547 (16)
H5A	0.3600	1.1192	0.2643	0.019*
C6	0.60259 (12)	0.95029 (9)	0.21274 (8)	0.01269 (15)
C7	0.54044 (11)	0.80676 (9)	0.23205 (8)	0.01258 (15)
C8	0.70206 (12)	0.66696 (9)	0.28388 (8)	0.01320 (15)
C9	0.67772 (13)	0.55204 (10)	0.36921 (8)	0.01689 (17)
H9A	0.5554	0.5601	0.4004	0.020*
C10	0.83112 (15)	0.42584 (11)	0.40902 (9)	0.02055 (18)
H10A	0.8126	0.3484	0.4668	0.025*
C11	1.01105 (14)	0.41270 (11)	0.36456 (9)	0.02113 (19)
H11A	1.1156	0.3280	0.3934	0.025*
C12	1.03761 (13)	0.52413 (10)	0.27754 (9)	0.01737 (17)
H12A	1.1602	0.5145	0.2460	0.021*
C13	0.88421 (12)	0.64985 (9)	0.23660 (8)	0.01354 (15)
C14	0.90580 (11)	0.76761 (9)	0.13675 (8)	0.01299 (15)
H14A	1.0400	0.7611	0.1273	0.016*
C15	0.84323 (12)	0.73065 (10)	0.01665 (8)	0.01417 (15)
H15A	0.8081	0.8262	−0.0392	0.017*
H15B	0.9498	0.6507	−0.0216	0.017*
C16	0.67958 (12)	0.67252 (10)	0.03665 (8)	0.01311 (15)
C17	0.50015 (12)	0.76547 (10)	0.10507 (8)	0.01383 (15)
H17A	0.4382	0.8650	0.0557	0.017*
C18	0.35765 (12)	0.83894 (10)	0.31087 (8)	0.01568 (16)
H18A	0.2566	0.9225	0.2683	0.019*
H18B	0.3227	0.7437	0.3195	0.019*
C19	0.36715 (13)	0.88655 (11)	0.43476 (8)	0.01713 (17)
H19A	0.4780	0.8350	0.4775	0.021*
C20	0.22942 (14)	0.99649 (11)	0.48766 (9)	0.02011 (18)
H20C	0.1170	1.0500	0.4471	0.024*
H20A	0.2434	1.0216	0.5660	0.024*
H1O2	0.412 (3)	0.602 (2)	0.0653 (18)	0.048 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0180 (3)	0.0167 (3)	0.0194 (3)	−0.0076 (2)	0.0007 (2)	−0.0050 (2)
O2	0.0168 (3)	0.0261 (3)	0.0222 (3)	−0.0133 (3)	0.0034 (2)	−0.0089 (3)
C1	0.0129 (3)	0.0129 (3)	0.0139 (4)	−0.0056 (3)	−0.0012 (3)	−0.0005 (3)
C2	0.0174 (4)	0.0158 (3)	0.0161 (4)	−0.0087 (3)	−0.0010 (3)	0.0000 (3)
C3	0.0244 (4)	0.0143 (3)	0.0192 (4)	−0.0094 (3)	−0.0022 (3)	0.0000 (3)
C4	0.0224 (4)	0.0121 (3)	0.0182 (4)	−0.0039 (3)	−0.0025 (3)	−0.0014 (3)
C5	0.0153 (4)	0.0143 (3)	0.0154 (4)	−0.0031 (3)	−0.0016 (3)	−0.0013 (3)
C6	0.0127 (3)	0.0126 (3)	0.0133 (3)	−0.0049 (3)	−0.0010 (3)	−0.0010 (3)
C7	0.0112 (3)	0.0139 (3)	0.0133 (4)	−0.0050 (3)	0.0005 (3)	−0.0020 (3)
C8	0.0141 (3)	0.0131 (3)	0.0132 (4)	−0.0056 (3)	−0.0005 (3)	−0.0010 (3)
C9	0.0201 (4)	0.0159 (4)	0.0157 (4)	−0.0082 (3)	0.0014 (3)	−0.0004 (3)
C10	0.0278 (5)	0.0154 (4)	0.0179 (4)	−0.0078 (3)	−0.0010 (3)	0.0029 (3)
C11	0.0235 (4)	0.0146 (4)	0.0218 (4)	−0.0022 (3)	−0.0042 (3)	0.0017 (3)
C12	0.0151 (4)	0.0157 (4)	0.0193 (4)	−0.0025 (3)	−0.0020 (3)	−0.0010 (3)
C13	0.0134 (3)	0.0128 (3)	0.0145 (4)	−0.0046 (3)	−0.0008 (3)	−0.0009 (3)
C14	0.0115 (3)	0.0134 (3)	0.0147 (4)	−0.0053 (3)	0.0007 (3)	−0.0009 (3)
C15	0.0134 (3)	0.0154 (3)	0.0150 (4)	−0.0069 (3)	0.0025 (3)	−0.0022 (3)
C16	0.0130 (3)	0.0146 (3)	0.0119 (3)	−0.0050 (3)	0.0000 (3)	−0.0010 (3)
C17	0.0116 (3)	0.0162 (3)	0.0151 (4)	−0.0062 (3)	0.0003 (3)	−0.0027 (3)
C18	0.0129 (3)	0.0197 (4)	0.0157 (4)	−0.0071 (3)	0.0017 (3)	−0.0035 (3)
C19	0.0157 (4)	0.0214 (4)	0.0156 (4)	−0.0079 (3)	0.0014 (3)	−0.0032 (3)
C20	0.0201 (4)	0.0223 (4)	0.0188 (4)	−0.0086 (3)	0.0040 (3)	−0.0044 (3)

Geometric parameters (Å, º) top

O1—C16	1.2198 (10)	C10—C11	1.3903 (14)
O2—C17	1.4034 (10)	C10—H10A	0.9500
O2—H1O2	0.948 (19)	C11—C12	1.3929 (13)
C1—C2	1.3957 (11)	C11—H11A	0.9500
C1—C6	1.4023 (11)	C12—C13	1.3955 (12)
C1—C14	1.5039 (11)	C12—H12A	0.9500
C2—C3	1.3945 (13)	C13—C14	1.5122 (12)
C2—H2A	0.9500	C14—C15	1.5622 (12)
C3—C4	1.3901 (14)	C14—H14A	1.0000
C3—H3A	0.9500	C15—C16	1.5081 (12)
C4—C5	1.3946 (12)	C15—H15A	0.9900
C4—H4A	0.9500	C15—H15B	0.9900
C5—C6	1.4024 (12)	C16—C17	1.5329 (12)
C5—H5A	0.9500	C17—H17A	1.0000
C6—C7	1.5342 (11)	C18—C19	1.5069 (13)
C7—C8	1.5369 (12)	C18—H18A	0.9900
C7—C18	1.5441 (12)	C18—H18B	0.9900
C7—C17	1.5822 (12)	C19—C20	1.3281 (13)
C8—C9	1.3988 (12)	C19—H19A	0.9500
C8—C13	1.4081 (12)	C20—H20C	0.9500
C9—C10	1.3939 (13)	C20—H20A	0.9500
C9—H9A	0.9500

C17—O2—H1O2	109.6 (11)	C11—C12—H12A	120.0
C2—C1—C6	120.78 (8)	C13—C12—H12A	120.0
C2—C1—C14	121.59 (8)	C12—C13—C8	120.62 (8)
C6—C1—C14	117.62 (7)	C12—C13—C14	121.59 (8)
C3—C2—C1	120.39 (8)	C8—C13—C14	117.74 (7)
C3—C2—H2A	119.8	C1—C14—C13	109.28 (7)
C1—C2—H2A	119.8	C1—C14—C15	110.01 (7)
C4—C3—C2	119.14 (8)	C13—C14—C15	109.10 (7)
C4—C3—H3A	120.4	C1—C14—H14A	109.5
C2—C3—H3A	120.4	C13—C14—H14A	109.5
C3—C4—C5	120.75 (8)	C15—C14—H14A	109.5
C3—C4—H4A	119.6	C16—C15—C14	112.12 (7)
C5—C4—H4A	119.6	C16—C15—H15A	109.2
C4—C5—C6	120.56 (8)	C14—C15—H15A	109.2
C4—C5—H5A	119.7	C16—C15—H15B	109.2
C6—C5—H5A	119.7	C14—C15—H15B	109.2
C5—C6—C1	118.33 (7)	H15A—C15—H15B	107.9
C5—C6—C7	123.79 (7)	O1—C16—C15	120.54 (8)
C1—C6—C7	117.88 (7)	O1—C16—C17	118.56 (8)
C6—C7—C8	109.17 (7)	C15—C16—C17	120.90 (7)
C6—C7—C18	111.72 (7)	O2—C17—C16	109.59 (7)
C8—C7—C18	112.73 (7)	O2—C17—C7	109.46 (7)
C6—C7—C17	108.29 (7)	C16—C17—C7	112.40 (7)
C8—C7—C17	107.27 (6)	O2—C17—H17A	108.4
C18—C7—C17	107.46 (7)	C16—C17—H17A	108.4
C9—C8—C13	118.50 (8)	C7—C17—H17A	108.4
C9—C8—C7	124.06 (8)	C19—C18—C7	115.09 (7)
C13—C8—C7	117.33 (7)	C19—C18—H18A	108.5
C10—C9—C8	120.67 (8)	C7—C18—H18A	108.5
C10—C9—H9A	119.7	C19—C18—H18B	108.5
C8—C9—H9A	119.7	C7—C18—H18B	108.5
C11—C10—C9	120.33 (8)	H18A—C18—H18B	107.5
C11—C10—H10A	119.8	C20—C19—C18	123.72 (9)
C9—C10—H10A	119.8	C20—C19—H19A	118.1
C10—C11—C12	119.80 (8)	C18—C19—H19A	118.1
C10—C11—H11A	120.1	C19—C20—H20C	120.0
C12—C11—H11A	120.1	C19—C20—H20A	120.0
C11—C12—C13	120.02 (9)	H20C—C20—H20A	120.0

C6—C1—C2—C3	0.18 (13)	C9—C8—C13—C12	−2.45 (13)
C14—C1—C2—C3	178.71 (8)	C7—C8—C13—C12	−178.77 (8)
C1—C2—C3—C4	−1.48 (14)	C9—C8—C13—C14	174.81 (8)
C2—C3—C4—C5	0.90 (14)	C7—C8—C13—C14	−1.50 (11)
C3—C4—C5—C6	1.00 (14)	C2—C1—C14—C13	136.26 (8)
C4—C5—C6—C1	−2.27 (13)	C6—C1—C14—C13	−45.17 (10)
C4—C5—C6—C7	178.01 (8)	C2—C1—C14—C15	−103.98 (9)
C2—C1—C6—C5	1.69 (13)	C6—C1—C14—C15	74.60 (9)
C14—C1—C6—C5	−176.90 (8)	C12—C13—C14—C1	−138.29 (8)
C2—C1—C6—C7	−178.58 (8)	C8—C13—C14—C1	44.47 (10)
C14—C1—C6—C7	2.83 (11)	C12—C13—C14—C15	101.38 (9)
C5—C6—C7—C8	−140.45 (8)	C8—C13—C14—C15	−75.85 (9)
C1—C6—C7—C8	39.84 (10)	C1—C14—C15—C16	−83.63 (8)
C5—C6—C7—C18	−15.07 (11)	C13—C14—C15—C16	36.24 (9)
C1—C6—C7—C18	165.21 (8)	C14—C15—C16—O1	−125.97 (9)
C5—C6—C7—C17	103.08 (9)	C14—C15—C16—C17	53.24 (10)
C1—C6—C7—C17	−76.64 (9)	O1—C16—C17—O2	4.54 (11)
C6—C7—C8—C9	143.59 (8)	C15—C16—C17—O2	−174.69 (7)
C18—C7—C8—C9	18.81 (12)	O1—C16—C17—C7	126.48 (8)
C17—C7—C8—C9	−99.29 (9)	C15—C16—C17—C7	−52.74 (10)
C6—C7—C8—C13	−40.32 (10)	C6—C7—C17—O2	−156.87 (7)
C18—C7—C8—C13	−165.10 (7)	C8—C7—C17—O2	85.43 (8)
C17—C7—C8—C13	76.81 (9)	C18—C7—C17—O2	−36.03 (9)
C13—C8—C9—C10	1.83 (13)	C6—C7—C17—C16	81.11 (8)
C7—C8—C9—C10	177.88 (8)	C8—C7—C17—C16	−36.59 (9)
C8—C9—C10—C11	0.19 (15)	C18—C7—C17—C16	−158.05 (7)
C9—C10—C11—C12	−1.64 (15)	C6—C7—C18—C19	−59.15 (10)
C10—C11—C12—C13	1.02 (15)	C8—C7—C18—C19	64.23 (10)
C11—C12—C13—C8	1.05 (14)	C17—C7—C18—C19	−177.80 (7)
C11—C12—C13—C14	−176.11 (8)	C7—C18—C19—C20	139.88 (9)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1	0.948 (18)	2.08 (2)	2.600 (2)	113 (2)
O2—H1O2···O1ⁱ	0.948 (18)	2.01 (2)	2.8041 (10)	140 (2)
C14—H14A···O2ⁱⁱ	1.00	2.41	3.3909 (12)	166
C17—H17A···Cg1ⁱⁱⁱ	1.00	2.92	3.6542 (10)	131
C20—H20A···Cg1^iv	0.95	2.79	3.6357 (11)	149

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y, z; (iii) −x+1, −y+2, −z; (iv) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈O₂
M_r	290.34
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.60940 (1), 9.16090 (1), 11.1735 (2)
α, β, γ (°)	84.202 (1), 85.707 (1), 69.895 (1)
V (Å³)	727.02 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.57 × 0.39 × 0.27

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.954, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	14851, 5283, 4634
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.759

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.130, 1.06
No. of reflections	5283
No. of parameters	203
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.26

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1	0.948 (18)	2.08 (2)	2.600 (2)	113 (2)
O2—H1O2···O1ⁱ	0.948 (18)	2.01 (2)	2.8041 (10)	140 (2)
C14—H14A···O2ⁱⁱ	1.00	2.41	3.3909 (12)	166
C17—H17A···Cg1ⁱⁱⁱ	1.00	2.92	3.6542 (10)	131
C20—H20A···Cg1^iv	0.9500	2.79	3.6357 (11)	149

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y, z; (iii) −x+1, −y+2, −z; (iv) −x+1, −y+2, −z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

UK, AIM and NA are grateful to the Deanship of Scientific Research, College of Science, King Saud University (KSU), for funding the synthetic chemistry work under Research Grant No. RGP-VPP-128.

References

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