(2E)-3-(3-Benzyl­oxyphen­yl)-1-(2-hydroxy-5-methyl­phen­yl)prop-2-en-1-one

Fun, H.-K.; Arshad, S.; Sarojini, B.K.; Khaleel, V.M.; Narayana, B.

doi:10.1107/S1600536811016977

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1372-o1373

doi:10.1107/S1600536811016977

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(2E)-3-(3-Benzyloxyphenyl)-1-(2-hydroxy-5-methylphenyl)prop-2-en-1-one

Hoong-Kun Fun,^a ^*‡ Suhana Arshad,^a B. K. Sarojini,^b V. Musthafa Khaleel ^b and B. Narayana ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, P. A. College of Engineering, Mangalore 574 153, India, and ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 28 April 2011; accepted 5 May 2011; online 11 May 2011)

In the molecule of the title compound, C₂₃H₂₀O₃, an intramolecular O—H⋯O hydrogen bond generates an S(6) ring. The central benzene ring makes dihedral angles of 80.17 (8) and 16.99 (7)°, respectively, with the benzyloxy and hydroxymethyl phenyl rings. In the crystal, molecules are linked via intermolecular C—H⋯O hydrogen bonds to form dimers. The dimers are connected by C—H⋯O hydrogen bonds and C—H⋯π interactions to form columns down the b axis.

Related literature

For general background and applications of chalcones, see: Awad et al. (1960 ); Coudert et al. (1988 ); Insuasty et al. (1992 , 1997 ); Kolos et al. (1996 ); Sarojini et al. (2006 ); Shettigar et al. (2010 ); Samshuddin et al. (2010 ); Fun et al. (2010 ). For related structures, see: Butcher et al. (2006 ); Ravishankar et al. (2003 , 2005 ); Narayana et al. (2007 ); Sarojini, Narayana et al. (2007 ); Sarojini, Yathirajan et al. (2007 ); Sharma et al. (1997 ); Jasinski et al. (2011 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₃H₂₀O₃
M_r = 344.39
Triclinic, $[P \overline 1]$
a = 8.7308 (5) Å
b = 9.5721 (5) Å
c = 11.5286 (6) Å
α = 106.547 (1)°
β = 94.572 (1)°
γ = 101.671 (1)°
V = 894.74 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.42 × 0.37 × 0.28 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.966, T_max = 0.977
18270 measured reflections
5238 independent reflections
3853 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.163
S = 1.03
5238 reflections
240 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C17–C22 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O3	0.93 (2)	1.65 (3)	2.521 (2)	155 (3)
C16—H16B⋯O3ⁱ	0.97	2.60	3.445 (2)	146
C22—H22A⋯O2ⁱⁱ	0.93	2.56	3.435 (2)	158
C11—H11A⋯Cg1ⁱⁱⁱ	0.93	2.80	3.660 (2)	153
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -z; (iii) x, y-1, z.

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/S1600536811016977/ci5187sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811016977/ci5187Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811016977/ci5187Isup3.cml

checkCIF report

Comment top

Chalcones (1,3-diarylpropenones) have been widely used as starting materials in numerous synthetic reactions (Awad et al., 1960; Coudert et al., 1988) including the preparation of fused-ring heterocyclic compounds (Insuasty et al., 1992, 1997; Kolos et al., 1996; Samshuddin et al., 2010; Fun et al., 2010). Chalcones are also finding application as organic nonlinear optical materials (NLO) for their SHG conversion efficiency (Sarojini et al., 2006; Shettigar et al., 2010). The crystal structures of some of the related chalcones viz 1-(3,4-dimethoxyphenyl)-3-(3-methylphenyl)prop-2-en-1-one (Sharma et al., 1997), 3-(3,4-dimethoxyphenyl)-1-(4-hydroxy-phenyl)prop-2-en-1-one (Ravishankar et al., 2003), 1-(4-chlorophenyl)-3-(4-hydroxyphenyl) prop-2-en-1-one (Ravishankar et al., 2005), 3-(3,4-dimethoxyphenyl)-1- (4-fluorophenyl)prop-2-en-1-one (Butcher et al., 2006), 3-(2-chlorophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one (Narayana et al., 2007), (2E)-1-(2-hydroxyphenyl)-3-(4-methoxy-phenyl)prop-2-en-1-one, (2E)-1-(2-hydroxyphenyl)-3-[4-(methyl-sulfanyl)phenyl]prop-2-en-1-one (Sarojini, Narayana et al., 2007; Sarojini, Yathirajan et al., 2007) and (2E)-3- (3,4-dimethoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one (Jasinski et al., 2011) have been reported. In continuation to our studies on structures of chalcones, we report here the crystal structure of a new chalcone, the title compound.

In the molecular structure (Fig. 1), an intramolecular O2—H1O2···O3 hydrogen bond (Table 1) forming an S(6) ring motif (Bernstein et al., 1995) is observed. The C1–C6 and C10–C15 benzene rings form a dihedral angle of 16.99 (7)° between them. In addition, they also make dihedral angles of 69.01 (7) and 80.17 (8)°, respectively, with the terminal phenyl ring (C17–C22). Bond lengths (Allen et al., 1987) and angles are within normal range.

The crystal packing is shown in Fig. 2. The molecules are linked by intermolecular C22—H22A···O2 hydrogen bonds (Table 1) to form dimers. Furthermore, these dimers are connected by intermolecular C16—H16B···O3 hydrogen bonds (Table 1) to form columns down the b axis. The C—H···π interactions (Table 1) which involve C11 and the C17–C22 phenyl ring further stabilize the crystal structure.

Related literature top

For general background and applications of chalcones, see: Awad et al. (1960); Coudert et al. (1988); Insuasty et al. (1992, 1997); Kolos et al. (1996); Sarojini et al. (2006); Shettigar et al. (2010); Samshuddin et al. (2010); Fun et al. (2010). For related structures, see: Butcher et al. (2006); Ravishankar et al. (2003, 2005); Narayana et al. (2007); Sarojini, Narayana et al. (2007); Sarojini, Yathirajan et al. (2007) ; Sharma et al. (1997); Jasinski et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987).

Experimental top

2-Hydroxy-5-methoxyacetophenone (1.66 g, 0.01 mol) was mixed with 4-benzyloxybenzaldehyde (2.12 g, 0.01 mol) and dissolved in ethanol (30 ml). To this solution, 3 ml of KOH (50%, 10 mL) was added at 5°C. The reaction mixture was stirred for 5 h and poured on to crushed ice. The pH of this mixture was adjusted to 3–4 with 2 M HCl aqueous solution. The resulting crude yellow solid was filtered, washed successively with dilute HCl solution and distilled water and finally recrystallized from ethanol (95%) to give the pure chalcone. Crystals suitable for X-ray diffraction studies were grown by slow evaporation of the solution of the compound in ethyl alcohol-DMF (4:1) mixture (m.p. 393–397 K). Composition: found (calculated) for C₂₃H₂₀O₃: C 76.65 (76.63), H 5.59 (5.57).

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 and the atom-numbering scheme. The dashed line indicates an intramolecular hydrogen bond.
	Fig. 2. The crystal packing of the title compound. Dashed lines represent hydrogen bonds.

(2E)-3-(3-Benzyloxyphenyl)-1-(2-hydroxy-5-methylphenyl)prop-2-en-1-one top

Crystal data top

C₂₃H₂₀O₃	Z = 2
M_r = 344.39	F(000) = 364
Triclinic, P1	D_x = 1.278 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7308 (5) Å	Cell parameters from 5803 reflections
b = 9.5721 (5) Å	θ = 2.8–30.0°
c = 11.5286 (6) Å	µ = 0.08 mm⁻¹
α = 106.547 (1)°	T = 296 K
β = 94.572 (1)°	Block, orange
γ = 101.671 (1)°	0.42 × 0.37 × 0.28 mm
V = 894.74 (8) Å³

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	5238 independent reflections
Radiation source: fine-focus sealed tube	3853 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 30.1°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
T_min = 0.966, T_max = 0.977	k = −13→13
18270 measured reflections	l = −15→16

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0847P)² + 0.1176P] where P = (F_o² + 2F_c²)/3
5238 reflections	(Δ/σ)_max = 0.001
240 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₃H₂₀O₃	γ = 101.671 (1)°
M_r = 344.39	V = 894.74 (8) Å³
Triclinic, P1	Z = 2
a = 8.7308 (5) Å	Mo Kα radiation
b = 9.5721 (5) Å	µ = 0.08 mm⁻¹
c = 11.5286 (6) Å	T = 296 K
α = 106.547 (1)°	0.42 × 0.37 × 0.28 mm
β = 94.572 (1)°

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	5238 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3853 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.977	R_int = 0.020
18270 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.26 e Å⁻³
5238 reflections	Δρ_min = −0.23 e Å⁻³
240 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	0.16772 (13)	0.30000 (11)	−0.13861 (10)	0.0679 (3)
O2	0.43323 (13)	−0.41373 (11)	0.37191 (11)	0.0644 (3)
O3	0.37319 (15)	−0.32210 (11)	0.19276 (10)	0.0681 (3)
C1	0.66751 (15)	−0.03177 (14)	0.42278 (11)	0.0459 (3)
H1A	0.6795	0.0439	0.3861	0.055*
C2	0.76064 (15)	−0.00671 (14)	0.53313 (11)	0.0485 (3)
C3	0.73915 (17)	−0.12245 (17)	0.58579 (13)	0.0552 (3)
H3A	0.8003	−0.1083	0.6599	0.066*
C4	0.63119 (17)	−0.25623 (16)	0.53216 (13)	0.0561 (3)
H4A	0.6195	−0.3308	0.5700	0.067*
C5	0.53927 (15)	−0.28026 (14)	0.42114 (12)	0.0475 (3)
C6	0.55590 (14)	−0.16674 (13)	0.36425 (10)	0.0428 (2)
C7	0.45402 (16)	−0.19356 (14)	0.24783 (11)	0.0475 (3)
C8	0.44225 (16)	−0.07006 (14)	0.19893 (11)	0.0484 (3)
H8A	0.5083	0.0245	0.2364	0.058*
C9	0.33780 (17)	−0.09225 (15)	0.10131 (12)	0.0526 (3)
H9A	0.2805	−0.1906	0.0646	0.063*
C10	0.30100 (16)	0.01655 (14)	0.04420 (11)	0.0490 (3)
C11	0.1932 (2)	−0.03475 (16)	−0.06343 (15)	0.0703 (5)
H11A	0.1479	−0.1369	−0.0963	0.084*
C12	0.1525 (2)	0.06119 (17)	−0.12187 (15)	0.0732 (5)
H12A	0.0811	0.0237	−0.1939	0.088*
C13	0.21741 (16)	0.21433 (14)	−0.07401 (12)	0.0511 (3)
C14	0.32657 (17)	0.26857 (15)	0.03205 (12)	0.0536 (3)
H14A	0.3720	0.3708	0.0644	0.064*
C15	0.36739 (17)	0.16958 (15)	0.08932 (12)	0.0537 (3)
H15A	0.4413	0.2066	0.1600	0.064*
C16	0.24447 (19)	0.45417 (15)	−0.10512 (15)	0.0644 (4)
H16A	0.3565	0.4657	−0.1101	0.077*
H16B	0.2321	0.5047	−0.0218	0.077*
C17	0.17020 (16)	0.52033 (13)	−0.19193 (13)	0.0526 (3)
C18	0.01997 (18)	0.54490 (19)	−0.18521 (17)	0.0677 (4)
H18A	−0.0364	0.5200	−0.1259	0.081*
C19	−0.04746 (19)	0.60627 (19)	−0.26593 (18)	0.0711 (4)
H19A	−0.1485	0.6225	−0.2604	0.085*
C20	0.0337 (2)	0.64284 (18)	−0.35342 (15)	0.0685 (4)
H20A	−0.0119	0.6837	−0.4077	0.082*
C21	0.1825 (2)	0.6194 (2)	−0.36131 (15)	0.0724 (4)
H21A	0.2380	0.6446	−0.4209	0.087*
C22	0.25088 (19)	0.55839 (17)	−0.28101 (14)	0.0615 (4)
H22A	0.3521	0.5429	−0.2871	0.074*
C23	0.87881 (19)	0.13954 (18)	0.59510 (15)	0.0658 (4)
H23A	0.8420	0.2194	0.5759	0.099*
H23B	0.9787	0.1346	0.5670	0.099*
H23C	0.8911	0.1579	0.6820	0.099*
H1O2	0.392 (3)	−0.406 (3)	0.298 (2)	0.110 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0792 (7)	0.0450 (5)	0.0711 (7)	0.0010 (5)	−0.0301 (5)	0.0254 (5)
O2	0.0715 (6)	0.0486 (5)	0.0734 (7)	0.0049 (4)	−0.0062 (5)	0.0304 (5)
O3	0.0917 (8)	0.0466 (5)	0.0566 (6)	0.0033 (5)	−0.0159 (5)	0.0173 (4)
C1	0.0530 (6)	0.0458 (6)	0.0430 (6)	0.0145 (5)	0.0042 (5)	0.0188 (5)
C2	0.0505 (6)	0.0519 (6)	0.0451 (6)	0.0164 (5)	0.0027 (5)	0.0162 (5)
C3	0.0606 (7)	0.0635 (8)	0.0473 (6)	0.0225 (6)	−0.0012 (5)	0.0232 (6)
C4	0.0668 (8)	0.0557 (7)	0.0561 (7)	0.0199 (6)	0.0032 (6)	0.0310 (6)
C5	0.0523 (6)	0.0452 (6)	0.0514 (6)	0.0162 (5)	0.0064 (5)	0.0217 (5)
C6	0.0498 (6)	0.0437 (6)	0.0397 (5)	0.0165 (5)	0.0050 (4)	0.0168 (4)
C7	0.0571 (7)	0.0454 (6)	0.0417 (6)	0.0137 (5)	0.0029 (5)	0.0162 (5)
C8	0.0589 (7)	0.0453 (6)	0.0431 (6)	0.0135 (5)	0.0012 (5)	0.0177 (5)
C9	0.0681 (8)	0.0453 (6)	0.0431 (6)	0.0117 (5)	−0.0031 (5)	0.0156 (5)
C10	0.0585 (7)	0.0458 (6)	0.0415 (6)	0.0108 (5)	−0.0038 (5)	0.0157 (5)
C11	0.0894 (11)	0.0432 (7)	0.0645 (9)	−0.0001 (7)	−0.0308 (8)	0.0175 (6)
C12	0.0889 (11)	0.0487 (7)	0.0666 (9)	−0.0018 (7)	−0.0384 (8)	0.0198 (7)
C13	0.0563 (7)	0.0444 (6)	0.0507 (7)	0.0082 (5)	−0.0092 (5)	0.0190 (5)
C14	0.0607 (7)	0.0423 (6)	0.0500 (7)	0.0045 (5)	−0.0112 (5)	0.0128 (5)
C15	0.0617 (7)	0.0495 (6)	0.0436 (6)	0.0075 (5)	−0.0129 (5)	0.0139 (5)
C16	0.0729 (9)	0.0446 (7)	0.0673 (9)	0.0019 (6)	−0.0206 (7)	0.0211 (6)
C17	0.0583 (7)	0.0372 (5)	0.0567 (7)	0.0047 (5)	−0.0095 (6)	0.0153 (5)
C18	0.0572 (8)	0.0691 (9)	0.0813 (10)	0.0046 (7)	0.0034 (7)	0.0390 (8)
C19	0.0524 (7)	0.0668 (9)	0.0942 (12)	0.0110 (7)	−0.0089 (7)	0.0323 (9)
C20	0.0812 (10)	0.0570 (8)	0.0655 (9)	0.0160 (7)	−0.0137 (8)	0.0229 (7)
C21	0.0939 (12)	0.0728 (10)	0.0581 (9)	0.0244 (9)	0.0113 (8)	0.0287 (8)
C22	0.0650 (8)	0.0560 (8)	0.0647 (8)	0.0207 (6)	0.0057 (7)	0.0172 (7)
C23	0.0657 (9)	0.0635 (8)	0.0607 (8)	0.0067 (7)	−0.0080 (7)	0.0178 (7)

Geometric parameters (Å, º) top

O1—C13	1.3622 (14)	C11—H11A	0.93
O1—C16	1.4178 (16)	C12—C13	1.3884 (18)
O2—C5	1.3551 (16)	C12—H12A	0.93
O2—H1O2	0.93 (3)	C13—C14	1.3876 (17)
O3—C7	1.2439 (16)	C14—C15	1.3843 (18)
C1—C2	1.3854 (17)	C14—H14A	0.93
C1—C6	1.4011 (17)	C15—H15A	0.93
C1—H1A	0.93	C16—C17	1.4990 (19)
C2—C3	1.3958 (19)	C16—H16A	0.97
C2—C23	1.504 (2)	C16—H16B	0.97
C3—C4	1.371 (2)	C17—C22	1.381 (2)
C3—H3A	0.93	C17—C18	1.383 (2)
C4—C5	1.3889 (18)	C18—C19	1.386 (2)
C4—H4A	0.93	C18—H18A	0.93
C5—C6	1.4104 (16)	C19—C20	1.363 (3)
C6—C7	1.4764 (16)	C19—H19A	0.93
C7—C8	1.4647 (17)	C20—C21	1.368 (3)
C8—C9	1.3286 (17)	C20—H20A	0.93
C8—H8A	0.93	C21—C22	1.384 (2)
C9—C10	1.4538 (17)	C21—H21A	0.93
C9—H9A	0.93	C22—H22A	0.93
C10—C15	1.3880 (18)	C23—H23A	0.96
C10—C11	1.3950 (18)	C23—H23B	0.96
C11—C12	1.3674 (19)	C23—H23C	0.96

C13—O1—C16	118.66 (10)	O1—C13—C12	115.52 (11)
C5—O2—H1O2	102.3 (15)	C14—C13—C12	119.36 (12)
C2—C1—C6	122.54 (11)	C15—C14—C13	119.56 (12)
C2—C1—H1A	118.7	C15—C14—H14A	120.2
C6—C1—H1A	118.7	C13—C14—H14A	120.2
C1—C2—C3	117.23 (12)	C14—C15—C10	121.81 (11)
C1—C2—C23	121.74 (12)	C14—C15—H15A	119.1
C3—C2—C23	121.03 (12)	C10—C15—H15A	119.1
C4—C3—C2	122.34 (12)	O1—C16—C17	107.69 (11)
C4—C3—H3A	118.8	O1—C16—H16A	110.2
C2—C3—H3A	118.8	C17—C16—H16A	110.2
C3—C4—C5	119.85 (12)	O1—C16—H16B	110.2
C3—C4—H4A	120.1	C17—C16—H16B	110.2
C5—C4—H4A	120.1	H16A—C16—H16B	108.5
O2—C5—C4	117.85 (11)	C22—C17—C18	118.30 (13)
O2—C5—C6	122.05 (11)	C22—C17—C16	120.52 (14)
C4—C5—C6	120.09 (12)	C18—C17—C16	121.18 (14)
C1—C6—C5	117.95 (11)	C17—C18—C19	120.67 (15)
C1—C6—C7	122.97 (10)	C17—C18—H18A	119.7
C5—C6—C7	119.07 (11)	C19—C18—H18A	119.7
O3—C7—C8	119.66 (11)	C20—C19—C18	120.23 (15)
O3—C7—C6	119.36 (11)	C20—C19—H19A	119.9
C8—C7—C6	120.94 (11)	C18—C19—H19A	119.9
C9—C8—C7	120.42 (12)	C19—C20—C21	119.87 (14)
C9—C8—H8A	119.8	C19—C20—H20A	120.1
C7—C8—H8A	119.8	C21—C20—H20A	120.1
C8—C9—C10	128.73 (12)	C20—C21—C22	120.30 (16)
C8—C9—H9A	115.6	C20—C21—H21A	119.8
C10—C9—H9A	115.6	C22—C21—H21A	119.8
C15—C10—C11	117.27 (12)	C17—C22—C21	120.62 (15)
C15—C10—C9	124.19 (11)	C17—C22—H22A	119.7
C11—C10—C9	118.54 (12)	C21—C22—H22A	119.7
C12—C11—C10	121.74 (13)	C2—C23—H23A	109.5
C12—C11—H11A	119.1	C2—C23—H23B	109.5
C10—C11—H11A	119.1	H23A—C23—H23B	109.5
C11—C12—C13	120.24 (12)	C2—C23—H23C	109.5
C11—C12—H12A	119.9	H23A—C23—H23C	109.5
C13—C12—H12A	119.9	H23B—C23—H23C	109.5
O1—C13—C14	125.12 (11)

C6—C1—C2—C3	−0.22 (19)	C9—C10—C11—C12	179.73 (17)
C6—C1—C2—C23	−179.44 (13)	C10—C11—C12—C13	−0.6 (3)
C1—C2—C3—C4	0.0 (2)	C16—O1—C13—C14	7.7 (2)
C23—C2—C3—C4	179.26 (14)	C16—O1—C13—C12	−171.44 (16)
C2—C3—C4—C5	0.4 (2)	C11—C12—C13—O1	−179.34 (17)
C3—C4—C5—O2	−179.51 (12)	C11—C12—C13—C14	1.5 (3)
C3—C4—C5—C6	−0.6 (2)	O1—C13—C14—C15	−179.99 (14)
C2—C1—C6—C5	0.00 (18)	C12—C13—C14—C15	−0.9 (2)
C2—C1—C6—C7	178.84 (11)	C13—C14—C15—C10	−0.6 (2)
O2—C5—C6—C1	179.27 (11)	C11—C10—C15—C14	1.4 (2)
C4—C5—C6—C1	0.41 (19)	C9—C10—C15—C14	−179.16 (13)
O2—C5—C6—C7	0.39 (19)	C13—O1—C16—C17	178.62 (13)
C4—C5—C6—C7	−178.47 (11)	O1—C16—C17—C22	−107.22 (16)
C1—C6—C7—O3	170.34 (13)	O1—C16—C17—C18	72.78 (18)
C5—C6—C7—O3	−10.84 (19)	C22—C17—C18—C19	0.0 (2)
C1—C6—C7—C8	−12.05 (19)	C16—C17—C18—C19	179.95 (14)
C5—C6—C7—C8	166.77 (11)	C17—C18—C19—C20	0.2 (3)
O3—C7—C8—C9	4.9 (2)	C18—C19—C20—C21	−0.2 (3)
C6—C7—C8—C9	−172.75 (12)	C19—C20—C21—C22	0.1 (3)
C7—C8—C9—C10	175.62 (13)	C18—C17—C22—C21	0.0 (2)
C8—C9—C10—C15	−3.7 (2)	C16—C17—C22—C21	179.96 (14)
C8—C9—C10—C11	175.79 (16)	C20—C21—C22—C17	0.0 (2)
C15—C10—C11—C12	−0.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O3	0.93 (2)	1.65 (3)	2.521 (2)	155 (3)
C16—H16B···O3ⁱ	0.97	2.60	3.445 (2)	146
C22—H22A···O2ⁱⁱ	0.93	2.56	3.435 (2)	158
C11—H11A···Cg1ⁱⁱⁱ	0.93	2.80	3.660 (2)	153

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

Experimental details

Crystal data
Chemical formula	C₂₃H₂₀O₃
M_r	344.39
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.7308 (5), 9.5721 (5), 11.5286 (6)
α, β, γ (°)	106.547 (1), 94.572 (1), 101.671 (1)
V (Å³)	894.74 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.42 × 0.37 × 0.28

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.966, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	18270, 5238, 3853
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.163, 1.03
No. of reflections	5238
No. of parameters	240
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.23

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O3	0.93 (2)	1.65 (3)	2.521 (2)	155 (3)
C16—H16B···O3ⁱ	0.97	2.60	3.445 (2)	146
C22—H22A···O2ⁱⁱ	0.93	2.56	3.435 (2)	158
C11—H11A···Cg1ⁱⁱⁱ	0.93	2.80	3.660 (2)	153

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). SA thanks the Malaysian government and USM for the award of a research scholarship. VMK thanks P. A. College of Engineering for research facilities.

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