(2E)-3-[3-(Benz­yloxy)phen­yl]-1-(2-hy­droxy­phen­yl)prop-2-en-1-one

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

doi:10.1107/S160053681101614X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1313-o1314

doi:10.1107/S160053681101614X

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(2E)-3-[3-(Benzyloxy)phenyl]-1-(2-hydroxyphenyl)prop-2-en-1-one

Hoong-Kun Fun,^a ^*‡ Wan-Sin Loh,^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 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 25 April 2011; accepted 28 April 2011; online 7 May 2011)

In the title compound, C₂₂H₁₈O₃, an intramolecular O—H⋯O hydrogen bond stabilizes the molecular structure, forming an S(6) ring motif. The central benzene ring forms a dihedral angle of 64.74 (5)° with the phenyl ring and a dihedral angle of 5.58 (5)° with the terminal benzene ring. In the crystal, molecules are linked into columns along the a axis via intermolecular C—H⋯O hydrogen bonds. C—H⋯π interactions involving the centroid of the hydroxy-substituted benzene ring further stabilize the crystal structure.

Related literature

For the background to chalcones, see: Awad et al. (1960 ); Coudert et al. (1988 ); Insuasty et al. (1992 , 1997 ); Kolos et al. (1996 ); Samshuddin et al. (2010 ); Fun et al. (2010 ); Sarojini et al. (2006 ); Shettigar et al. (2010 ); Sharma et al. (1997 ); Ravishankar et al. (2003 , 2005 ); Butcher et al. (2006 ); Narayana et al. (2007 ); Sarojini et al. (2007a ,b ); Jasinski et al. (2011 ). For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₂H₁₈O₃
M_r = 330.36
Monoclinic, P 2₁ /c
a = 6.6343 (1) Å
b = 35.7706 (5) Å
c = 8.1537 (1) Å
β = 121.879 (1)°
V = 1643.12 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.46 × 0.41 × 0.28 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.960, T_max = 0.976
23662 measured reflections
5994 independent reflections
5154 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.126
S = 1.04
5994 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C17–C22 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1⋯O2	0.96	1.62	2.5121 (11)	152
C5—H5A⋯O3ⁱ	0.93	2.47	3.3912 (13)	170
C18—H18A⋯O3ⁱⁱ	0.93	2.48	3.1235 (16)	127
C7—H7B⋯Cg1ⁱ	0.97	2.75	3.6633 (11)	158
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x-1, y, 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/S160053681101614X/sj5129sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681101614X/sj5129Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681101614X/sj5129Isup3.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 et al., 2007a,b) and (2E)-3-(2-anthryl)-1-(2-hydroxyphenyl)prop-2-en-1-one (Jasinski et al., 2011) have been reported. In a continuation of our studies of the structures of chalcones, we report the crystal structure of a new chalcone, (2E)-3-(3-benzyloxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one, C₂₂H₁₈O₃, (I).

The molecular strucure of (I) is shown in Fig. 1. An intramolecular O3—H1···O2 hydrogen bond (Table 1) stabilized the molecular structure, forming an S(6) ring motif (Bernstein et al., 1995). The (C8–C13) benzene ring forms a dihedral angle of 64.74 (5)° with the C1–C6 phenyl ring and is almost co-planar with the C17–C22 phenyl ring with a dihedral angle of 5.58 (5)°. Bond lengths (Allen et al., 1987) and angles are within the normal ranges.

In the crystal packing (Fig. 2), the molecules are linked into columns along the a axis via intermolecular C5—H5A···O3 and C18—H18A···O3 hydrogen bonds (Table 1). C–H···π interactions (Table 1) involving the centroids of C17–C22 rings (Cg1) further stabilize the crystal structure.

Related literature top

For the background to chalcones, see: Awad et al. (1960); Coudert et al. (1988); Insuasty et al. (1992, 1997); Kolos et al. (1996); Samshuddin et al. (2010); Fun et al. (2010); Sarojini et al. (2006); Shettigar et al. (2010); Sharma et al. (1997); Ravishankar et al. (2003, 2005); Butcher et al. (2006); Narayana et al. (2007); Sarojini et al. (2007a,b); Jasinski et al. (2011). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

2-Hydroxyacetophenone (1.36 g, 0.01 mol) was mixed with 4-benzyloxybenzaldehyde (2.12 g, 0.01 mol) and dissolved in ethanol (40 ml). To this solution 4 ml of KOH (50%) was added at 278 K. The reaction mixture was stirred for 8 h and poured onto 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 the slow evaporation of the solution of the compound in ethyl alcohol (m. p.: 367–369 K). Composition: Found (calculated) for C₂₂H₁₈O₃, C 79.98 (79.93); H: 5.49 (5.52).

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 the intramolecular hydrogen bond.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

(2E)-3-[3-(Benzyloxy)phenyl]-1-(2-hydroxyphenyl)prop-2-en-1-one top

Crystal data top

C₂₂H₁₈O₃	F(000) = 696
M_r = 330.36	D_x = 1.335 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9442 reflections
a = 6.6343 (1) Å	θ = 3.0–32.7°
b = 35.7706 (5) Å	µ = 0.09 mm⁻¹
c = 8.1537 (1) Å	T = 100 K
β = 121.879 (1)°	Block, yellow
V = 1643.12 (4) Å³	0.46 × 0.41 × 0.28 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5994 independent reflections
Radiation source: fine-focus sealed tube	5154 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 32.7°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→9
T_min = 0.960, T_max = 0.976	k = −54→54
23662 measured reflections	l = −12→12

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0608P)² + 0.6186P] where P = (F_o² + 2F_c²)/3
5994 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₂H₁₈O₃	V = 1643.12 (4) Å³
M_r = 330.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.6343 (1) Å	µ = 0.09 mm⁻¹
b = 35.7706 (5) Å	T = 100 K
c = 8.1537 (1) Å	0.46 × 0.41 × 0.28 mm
β = 121.879 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5994 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5154 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.976	R_int = 0.024
23662 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.04	Δρ_max = 0.47 e Å⁻³
5994 reflections	Δρ_min = −0.21 e Å⁻³
226 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	0.22678 (13)	−0.12255 (2)	0.64011 (11)	0.01788 (14)
O2	1.16788 (13)	0.04531 (2)	0.73546 (11)	0.01926 (15)
O3	1.37772 (13)	0.10727 (2)	0.82954 (12)	0.01960 (15)
H1	1.3290	0.0824	0.7790	0.029*
C1	0.1804 (2)	−0.21718 (3)	0.69912 (16)	0.0233 (2)
H1A	0.3438	−0.2209	0.7668	0.028*
C2	0.0347 (3)	−0.24325 (3)	0.71398 (18)	0.0297 (3)
H2A	0.1013	−0.2641	0.7926	0.036*
C3	−0.2084 (2)	−0.23818 (3)	0.61239 (18)	0.0283 (2)
H3A	−0.3055	−0.2557	0.6219	0.034*
C4	−0.3076 (2)	−0.20672 (3)	0.49557 (17)	0.0238 (2)
H4A	−0.4713	−0.2033	0.4264	0.029*
C5	−0.16259 (19)	−0.18037 (3)	0.48208 (15)	0.01870 (18)
H5A	−0.2296	−0.1593	0.4053	0.022*
C6	0.08311 (18)	−0.18549 (3)	0.58347 (14)	0.01668 (17)
C7	0.24046 (18)	−0.15803 (3)	0.56323 (14)	0.01653 (17)
H7A	0.4030	−0.1670	0.6331	0.020*
H7B	0.1891	−0.1553	0.4282	0.020*
C8	0.37550 (16)	−0.09508 (3)	0.64855 (13)	0.01453 (16)
C9	0.53008 (17)	−0.09903 (3)	0.58253 (14)	0.01643 (17)
H9A	0.5357	−0.1213	0.5262	0.020*
C10	0.67596 (17)	−0.06915 (3)	0.60209 (14)	0.01585 (17)
H10A	0.7794	−0.0719	0.5585	0.019*
C11	0.67167 (16)	−0.03522 (3)	0.68526 (13)	0.01424 (16)
C12	0.51140 (17)	−0.03170 (3)	0.74868 (14)	0.01541 (17)
H12A	0.5032	−0.0093	0.8028	0.018*
C13	0.36650 (17)	−0.06120 (3)	0.73120 (14)	0.01546 (17)
H13A	0.2626	−0.0586	0.7744	0.019*
C14	0.83060 (17)	−0.00553 (3)	0.70116 (13)	0.01512 (17)
H14A	0.9183	−0.0100	0.6443	0.018*
C15	0.86482 (17)	0.02778 (3)	0.78915 (14)	0.01564 (17)
H15A	0.7793	0.0338	0.8463	0.019*
C16	1.03580 (16)	0.05459 (3)	0.79541 (13)	0.01431 (16)
C17	1.05437 (16)	0.09259 (3)	0.87343 (13)	0.01351 (16)
C18	0.90277 (17)	0.10566 (3)	0.93231 (14)	0.01700 (17)
H18A	0.7872	0.0898	0.9246	0.020*
C19	0.92093 (19)	0.14160 (3)	1.00144 (15)	0.02028 (19)
H19A	0.8178	0.1497	1.0388	0.024*
C20	1.09498 (19)	0.16556 (3)	1.01480 (15)	0.01988 (19)
H20A	1.1082	0.1897	1.0618	0.024*
C21	1.24825 (18)	0.15361 (3)	0.95848 (14)	0.01802 (18)
H21A	1.3642	0.1697	0.9682	0.022*
C22	1.22862 (16)	0.11736 (3)	0.88693 (13)	0.01474 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0210 (3)	0.0121 (3)	0.0250 (4)	−0.0031 (2)	0.0152 (3)	−0.0037 (3)
O2	0.0199 (3)	0.0171 (3)	0.0267 (4)	−0.0001 (3)	0.0163 (3)	−0.0017 (3)
O3	0.0174 (3)	0.0188 (3)	0.0277 (4)	−0.0011 (3)	0.0154 (3)	−0.0008 (3)
C1	0.0310 (5)	0.0153 (4)	0.0192 (5)	0.0003 (4)	0.0103 (4)	0.0007 (3)
C2	0.0488 (7)	0.0159 (5)	0.0248 (5)	−0.0033 (5)	0.0197 (5)	0.0015 (4)
C3	0.0467 (7)	0.0181 (5)	0.0315 (6)	−0.0120 (5)	0.0284 (5)	−0.0067 (4)
C4	0.0291 (5)	0.0209 (5)	0.0293 (5)	−0.0068 (4)	0.0207 (5)	−0.0066 (4)
C5	0.0239 (5)	0.0151 (4)	0.0212 (4)	−0.0005 (3)	0.0148 (4)	−0.0015 (3)
C6	0.0233 (4)	0.0123 (4)	0.0156 (4)	−0.0013 (3)	0.0110 (3)	−0.0024 (3)
C7	0.0195 (4)	0.0131 (4)	0.0177 (4)	0.0000 (3)	0.0103 (3)	−0.0017 (3)
C8	0.0145 (4)	0.0131 (4)	0.0155 (4)	−0.0004 (3)	0.0076 (3)	−0.0002 (3)
C9	0.0179 (4)	0.0145 (4)	0.0181 (4)	−0.0010 (3)	0.0104 (3)	−0.0028 (3)
C10	0.0167 (4)	0.0157 (4)	0.0165 (4)	−0.0002 (3)	0.0098 (3)	−0.0009 (3)
C11	0.0145 (4)	0.0133 (4)	0.0140 (4)	0.0004 (3)	0.0069 (3)	0.0009 (3)
C12	0.0168 (4)	0.0121 (4)	0.0171 (4)	0.0007 (3)	0.0089 (3)	0.0001 (3)
C13	0.0167 (4)	0.0139 (4)	0.0179 (4)	0.0010 (3)	0.0105 (3)	−0.0001 (3)
C14	0.0147 (4)	0.0146 (4)	0.0153 (4)	0.0006 (3)	0.0074 (3)	0.0018 (3)
C15	0.0163 (4)	0.0153 (4)	0.0169 (4)	−0.0005 (3)	0.0098 (3)	0.0005 (3)
C16	0.0140 (4)	0.0141 (4)	0.0146 (4)	0.0005 (3)	0.0074 (3)	0.0010 (3)
C17	0.0129 (4)	0.0134 (4)	0.0146 (4)	0.0005 (3)	0.0075 (3)	0.0003 (3)
C18	0.0166 (4)	0.0177 (4)	0.0193 (4)	0.0002 (3)	0.0113 (3)	−0.0008 (3)
C19	0.0217 (5)	0.0207 (5)	0.0215 (5)	0.0022 (4)	0.0136 (4)	−0.0025 (3)
C20	0.0237 (5)	0.0169 (4)	0.0169 (4)	0.0007 (3)	0.0093 (4)	−0.0022 (3)
C21	0.0184 (4)	0.0157 (4)	0.0178 (4)	−0.0034 (3)	0.0080 (3)	−0.0017 (3)
C22	0.0130 (4)	0.0162 (4)	0.0146 (4)	0.0004 (3)	0.0070 (3)	0.0011 (3)

Geometric parameters (Å, º) top

O1—C8	1.3683 (11)	C10—C11	1.3978 (13)
O1—C7	1.4395 (12)	C10—H10A	0.9300
O2—C16	1.2528 (11)	C11—C12	1.4123 (13)
O3—C22	1.3477 (11)	C11—C14	1.4535 (13)
O3—H1	0.9618	C12—C13	1.3833 (13)
C1—C2	1.3942 (17)	C12—H12A	0.9300
C1—C6	1.3956 (14)	C13—H13A	0.9300
C1—H1A	0.9300	C14—C15	1.3467 (13)
C2—C3	1.382 (2)	C14—H14A	0.9300
C2—H2A	0.9300	C15—C16	1.4656 (13)
C3—C4	1.3946 (17)	C15—H15A	0.9300
C3—H3A	0.9300	C16—C17	1.4780 (13)
C4—C5	1.3924 (14)	C17—C18	1.4038 (13)
C4—H4A	0.9300	C17—C22	1.4139 (13)
C5—C6	1.3966 (15)	C18—C19	1.3833 (14)
C5—H5A	0.9300	C18—H18A	0.9300
C6—C7	1.5044 (14)	C19—C20	1.3952 (15)
C7—H7A	0.9700	C19—H19A	0.9300
C7—H7B	0.9700	C20—C21	1.3860 (15)
C8—C9	1.3945 (13)	C20—H20A	0.9300
C8—C13	1.4031 (13)	C21—C22	1.3996 (14)
C9—C10	1.3933 (13)	C21—H21A	0.9300
C9—H9A	0.9300

C8—O1—C7	116.46 (7)	C10—C11—C14	118.56 (8)
C22—O3—H1	104.7	C12—C11—C14	123.57 (8)
C2—C1—C6	120.49 (11)	C13—C12—C11	120.71 (9)
C2—C1—H1A	119.8	C13—C12—H12A	119.6
C6—C1—H1A	119.8	C11—C12—H12A	119.6
C3—C2—C1	120.24 (11)	C12—C13—C8	120.33 (9)
C3—C2—H2A	119.9	C12—C13—H13A	119.8
C1—C2—H2A	119.9	C8—C13—H13A	119.8
C2—C3—C4	119.74 (11)	C15—C14—C11	127.18 (9)
C2—C3—H3A	120.1	C15—C14—H14A	116.4
C4—C3—H3A	120.1	C11—C14—H14A	116.4
C5—C4—C3	120.24 (11)	C14—C15—C16	120.47 (9)
C5—C4—H4A	119.9	C14—C15—H15A	119.8
C3—C4—H4A	119.9	C16—C15—H15A	119.8
C4—C5—C6	120.25 (10)	O2—C16—C15	120.07 (9)
C4—C5—H5A	119.9	O2—C16—C17	119.68 (8)
C6—C5—H5A	119.9	C15—C16—C17	120.26 (8)
C1—C6—C5	119.03 (10)	C18—C17—C22	117.95 (9)
C1—C6—C7	120.27 (9)	C18—C17—C16	122.79 (8)
C5—C6—C7	120.66 (9)	C22—C17—C16	119.25 (8)
O1—C7—C6	108.71 (8)	C19—C18—C17	121.67 (9)
O1—C7—H7A	109.9	C19—C18—H18A	119.2
C6—C7—H7A	109.9	C17—C18—H18A	119.2
O1—C7—H7B	109.9	C18—C19—C20	119.54 (9)
C6—C7—H7B	109.9	C18—C19—H19A	120.2
H7A—C7—H7B	108.3	C20—C19—H19A	120.2
O1—C8—C9	124.44 (8)	C21—C20—C19	120.43 (9)
O1—C8—C13	115.60 (8)	C21—C20—H20A	119.8
C9—C8—C13	119.96 (9)	C19—C20—H20A	119.8
C10—C9—C8	119.09 (9)	C20—C21—C22	120.05 (9)
C10—C9—H9A	120.5	C20—C21—H21A	120.0
C8—C9—H9A	120.5	C22—C21—H21A	120.0
C9—C10—C11	122.04 (9)	O3—C22—C21	117.97 (9)
C9—C10—H10A	119.0	O3—C22—C17	121.68 (9)
C11—C10—H10A	119.0	C21—C22—C17	120.35 (9)
C10—C11—C12	117.87 (8)

C6—C1—C2—C3	0.73 (17)	C9—C8—C13—C12	−0.39 (14)
C1—C2—C3—C4	−0.38 (17)	C10—C11—C14—C15	−174.62 (9)
C2—C3—C4—C5	−0.40 (17)	C12—C11—C14—C15	5.66 (15)
C3—C4—C5—C6	0.83 (16)	C11—C14—C15—C16	178.92 (9)
C2—C1—C6—C5	−0.30 (15)	C14—C15—C16—O2	−6.92 (14)
C2—C1—C6—C7	−178.15 (10)	C14—C15—C16—C17	173.44 (9)
C4—C5—C6—C1	−0.47 (15)	O2—C16—C17—C18	176.07 (9)
C4—C5—C6—C7	177.37 (9)	C15—C16—C17—C18	−4.29 (14)
C8—O1—C7—C6	174.51 (8)	O2—C16—C17—C22	−2.76 (13)
C1—C6—C7—O1	−117.15 (10)	C15—C16—C17—C22	176.88 (8)
C5—C6—C7—O1	65.04 (11)	C22—C17—C18—C19	0.09 (14)
C7—O1—C8—C9	2.20 (13)	C16—C17—C18—C19	−178.75 (9)
C7—O1—C8—C13	−177.49 (8)	C17—C18—C19—C20	−0.48 (15)
O1—C8—C9—C10	−178.92 (9)	C18—C19—C20—C21	0.32 (16)
C13—C8—C9—C10	0.75 (14)	C19—C20—C21—C22	0.24 (15)
C8—C9—C10—C11	−0.25 (15)	C20—C21—C22—O3	178.42 (9)
C9—C10—C11—C12	−0.60 (14)	C20—C21—C22—C17	−0.64 (14)
C9—C10—C11—C14	179.67 (9)	C18—C17—C22—O3	−178.55 (9)
C10—C11—C12—C13	0.97 (14)	C16—C17—C22—O3	0.33 (14)
C14—C11—C12—C13	−179.32 (9)	C18—C17—C22—C21	0.47 (14)
C11—C12—C13—C8	−0.49 (14)	C16—C17—C22—C21	179.36 (8)
O1—C8—C13—C12	179.31 (8)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C17–C22 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O2	0.96	1.62	2.5121 (11)	152
C5—H5A···O3ⁱ	0.93	2.47	3.3912 (13)	170
C18—H18A···O3ⁱⁱ	0.93	2.48	3.1235 (16)	127
C7—H7B···Cg1ⁱ	0.97	2.75	3.6633 (11)	158

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₈O₃
M_r	330.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	6.6343 (1), 35.7706 (5), 8.1537 (1)
β (°)	121.879 (1)
V (Å³)	1643.12 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.46 × 0.41 × 0.28

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.960, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	23662, 5994, 5154
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.760

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.126, 1.04
No. of reflections	5994
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.21

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

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C17–C22 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O2	0.96	1.62	2.5121 (11)	152
C5—H5A···O3ⁱ	0.93	2.47	3.3912 (13)	170
C18—H18A···O3ⁱⁱ	0.93	2.48	3.1235 (16)	127
C7—H7B···Cg1ⁱ	0.97	2.75	3.6633 (11)	158

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: C-7581-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of a research fellowship. VMK thanks P. A. College of Engineering for the research facilities.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Awad, W., El-Neweihy, M. & Selim, F. (1960). J. Org. Chem. 25, 1333–1336. CrossRef CAS Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Butcher, R. J., Yathirajan, H. S., Anilkumar, H. G., Sarojini, B. K. & Narayana, B. (2006). Acta Cryst. E62, o1633–o1635. Web of Science CSD CrossRef IUCr Journals Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Coudert, P., Couquelet, J. & Tronche, P. (1988). J. Heterocycl. Chem. 25, 799–802. CrossRef CAS Google Scholar
Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010). Acta Cryst. E66, o864–o865. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Insuasty, B., Abonia, R. & Quiroga, J. (1992). An. Quim. 88, 718–720. Google Scholar
Insuasty, B., Quiroga, J. & Meier, H. (1997). Trends Heterocycl. Chem. 5, 83–89. CAS Google Scholar
Jasinski, J. P., Butcher, R. J., Musthafa Khaleel, V., Sarojini, B. K. & Yathirajan, H. S. (2011). Acta Cryst. E67, o795. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kolos, N., Orlov, V., Arisa, D., Shishkin, O., Struchkov, T. & Vorobiova, N. (1996). Khim. Geterotsikl. Soedin. pp. 87–95; Chem. Abstr. 125, 195600. Google Scholar
Narayana, B., Lakshmana, K., Sarojini, B. K., Yathirajan, H. S. & Bolte, M. (2007). Private communication. Google Scholar
Ravishankar, T., Chinnakali, K., Nanjundan, S., Selvam, P., Fun, H.-K. & Yu, X.-L. (2005). Acta Cryst. E61, o405–o407. CSD CrossRef IUCr Journals Google Scholar
Ravishankar, T., Chinnakali, K., Nanjundan, S., Selvamalar, C. S. J., Ramnathan, A., Usman, A. & Fun, H.-K. (2003). Acta Cryst. E59, o1143–o1145. Web of Science CSD CrossRef IUCr Journals Google Scholar
Samshuddin, S., Narayana, B., Yathirajan, H. S., Safwan, A. P. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1279–o1280. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sarojini, B. K., Narayana, B., Ashalatha, B. V., Indira, J. & Lobo, K. J. (2006). J. Cryst. Growth, 295, 54–59. Web of Science CrossRef CAS Google Scholar
Sarojini, B. K., Narayana, B., Mayekar, A. N., Yathirajan, H. S. & Bolte, M. (2007a). Acta Cryst. E63, o4447. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sarojini, B. K., Yathirajan, H. S., Mustafa, K., Sarfraz, H. & Bolte, M. (2007b). Acta Cryst. E63, o4448. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sharma, N. K., Kumar, R., Parmar, V. S. & Errington, W. (1997). Acta Cryst. C53, 1438–1440. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shettigar, S., Poornesh, P., Umesh, G., Sarojini, B. K., Narayana, B. & Prakash Kamath, K. (2010). Opt. Laser Technol. 42, 1162–1166. CrossRef CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 6| June 2011| Pages o1313-o1314

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