(E)-3-(Anthracen-9-yl)-1-(furan-2-yl)prop-2-en-1-one

Horkaew, J.; Suwunwong, T.; Chantrapromma, S.; Karalai, C.; Fun, H.-K.

doi:10.1107/S1600536810005982

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages o800-o801

doi:10.1107/S1600536810005982

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(E)-3-(Anthracen-9-yl)-1-(furan-2-yl)prop-2-en-1-one †

Jirapa Horkaew,^a Thitipone Suwunwong,^a Suchada Chantrapromma,^a ^*‡ Chatchanok Karalai ^a and Hoong-Kun Fun ^b §

^aCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: suchada.c@psu.ac.th

(Received 1 February 2010; accepted 14 February 2010; online 13 March 2010)

In the molecule of the title heteroaryl chalcone derivative, C₂₁H₁₄O₂, the almost planar prop-2-en-1-one unit [r.m.s. deviation = 0.0087 (1) Å] forms dihedral angles of 5.81 (7) and 49.85 (6)°, respectively, with the furan ring and anthracene ring system. In the crystal structure, the molecules are linked into a two-dimensional network parallel to (100) by C—H⋯O hydrogen bonds and π⋯π interactions involving the furan rings [centroid–centroid distance = 3.7205 (6) Å].

Related literature

For background and applications of chalcones, see: Gaber et al. (2008 ); Niu et al. (2006 ); Xu et al. (2005 ). For related structures, see: Chantrapromma et al. (2009 , 2010 ); Fun et al. (2009 ); Suwunwong et al. (2009 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₁H₁₄O₂
M_r = 298.32
Monoclinic, P 2₁ /c
a = 21.5743 (4) Å
b = 5.4571 (1) Å
c = 12.8394 (2) Å
β = 104.099 (1)°
V = 1466.09 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.55 × 0.25 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.955, T_max = 0.994
19468 measured reflections
4251 independent reflections
3549 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.118
S = 1.03
4251 reflections
264 parameters
All H-atom parameters refined
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.98 (2)	2.34 (2)	3.2871 (14)	165 (1)
C6—H6⋯O1ⁱ	0.94 (2)	2.40 (2)	3.3366 (13)	173 (1)
C19—H19⋯O1ⁱⁱ	0.98 (1)	2.47 (1)	3.3419 (13)	148 (1)
Symmetry codes: (i) x, y+1, z; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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/S1600536810005982/ci5032sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005982/ci5032Isup2.hkl

checkCIF report

Comment top

Chalcones have been studied for their wide range of applications including laser activity (Gaber et al., 2008) and fluorescence properties (Niu et al., 2006; Xu et al., 2005). We have previously reported crystal structures of several chalcone derivatives containing the anthracene moiety which exist in E configuration (Suwunwong et al., 2009) or Z configuration (Chantrapromma et al., 2009, 2010; Fun et al., 2009). The title compound was synthesized on account of its fluorescence properties. The crystal structure determination was undertaken to elucidate its conformation and to study the structure and fluorescence activity relationship.

The molecule of the title chalcone derivative (Fig. 1) exists in an E configuration with respect to the C6═C7 ethenyl bond, with a C5—C6—C7—C8 torsion angle of 178.00 (9)°. The anthracene ring system (C8–C21) is essentially planar (r.m.s. deviation = 0.0258 (1) Å). The prop-2-en-1-one unit (C5–C7/O1) is also planar (r.m.s. deviation = 0.0087 (1) Å; O1—C5—C6—C7 = 2.92 (15)°) and it forms dihedral angles of 5.81 (7) and 49.85 (6)°, respectively, with the furan ring and anthracene ring system. The interplanar angle between the furan ring and anthracene ring system is 48.53 (5)°. The bond distances show normal values (Allen et al., 1987) and are comparable with those in closely related structures (Chantrapromma, Horkaew et al., 2009; Chantrapromma, Suwunwong et al., 2010; Fun et al., 2009; Suwunwong et al., 2009).

In the crystal structure, the molecules are linked into a two-dimensional network parallel to the (100) by C—H···O hydrogen bonds (Fig. 2 and Table 1) and π···π interactions between the furan rings at (x, y, z) and (-x, 1-y, -z) [centroid···centroid distance = 3.7205 (6) Å].

Related literature top

For background and applications of chalcones, see: Gaber et al. (2008); Niu et al. (2006); Xu et al. (2005). For related structures, see: Chantrapromma et al. (2009, 2010); Fun et al. (2009); Suwunwong et al. (2009). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was synthesized by the condensation of anthracene-9-carbaldehyde (0.41 g, 2 mmol) with 2-furylmethylketone (0.22 g, 2 mmol) in ethanol (30 ml) in the presence of 30 % aqueous NaOH (5 ml) at room temperature. The reaction mixture was stirred at 278 K for 3 h and then a yellow solid appeared was collected by filtration, washed with acetone and dried in air. Yellow plate-shaped single crystals of the title compound suitable for X-ray structure determination were recrystalized from acetone-ethanol (1:1 v/v) by slow evaporation of the solvent at room temperature after several days (m.p. 423-424 K).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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.
	Fig. 2. The crystal packing of the title compound viewed along the b axis. C—H···O hydrogen bonds are shown as dashed lines.

(E)-3-(anthracen-9-yl)-1-(furan-2-yl)prop-2-en-1-one top

Crystal data top

C₂₁H₁₄O₂	F(000) = 624
M_r = 298.32	D_x = 1.352 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 423–424 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 21.5743 (4) Å	Cell parameters from 4251 reflections
b = 5.4571 (1) Å	θ = 2.9–30.0°
c = 12.8394 (2) Å	µ = 0.09 mm⁻¹
β = 104.099 (1)°	T = 100 K
V = 1466.09 (4) Å³	Plate, yellow
Z = 4	0.55 × 0.25 × 0.07 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4251 independent reflections
Radiation source: sealed tube	3549 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −26→30
T_min = 0.955, T_max = 0.994	k = −7→7
19468 measured reflections	l = −17→18

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	All H-atom parameters refined
S = 1.03	w = 1/[σ²(F_o²) + (0.0624P)² + 0.4737P] where P = (F_o² + 2F_c²)/3
4251 reflections	(Δ/σ)_max = 0.001
264 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₁H₁₄O₂	V = 1466.09 (4) Å³
M_r = 298.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 21.5743 (4) Å	µ = 0.09 mm⁻¹
b = 5.4571 (1) Å	T = 100 K
c = 12.8394 (2) Å	0.55 × 0.25 × 0.07 mm
β = 104.099 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4251 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3549 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.994	R_int = 0.029
19468 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.118	All H-atom parameters refined
S = 1.03	Δρ_max = 0.37 e Å⁻³
4251 reflections	Δρ_min = −0.22 e Å⁻³
264 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 120.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.13071 (4)	0.32065 (14)	0.15881 (6)	0.02003 (17)
O2	0.00592 (3)	0.46137 (14)	0.12589 (6)	0.01846 (17)
C1	−0.04942 (5)	0.5903 (2)	0.11274 (9)	0.0201 (2)
H1	−0.0880 (7)	0.489 (3)	0.1018 (12)	0.030 (4)*
C2	−0.03863 (5)	0.8346 (2)	0.11454 (9)	0.0208 (2)
H2	−0.0701 (8)	0.964 (3)	0.1084 (13)	0.034 (4)*
C3	0.02854 (5)	0.8641 (2)	0.12983 (8)	0.0177 (2)
H3	0.0517 (7)	1.019 (3)	0.1342 (11)	0.027 (4)*
C4	0.05367 (5)	0.63332 (19)	0.13651 (8)	0.0152 (2)
C5	0.11877 (5)	0.54141 (19)	0.15040 (8)	0.0150 (2)
C6	0.16862 (5)	0.72918 (19)	0.15159 (8)	0.0163 (2)
C7	0.22914 (5)	0.66214 (19)	0.15739 (8)	0.0159 (2)
C8	0.28183 (5)	0.83333 (19)	0.15569 (8)	0.01475 (19)
C9	0.34004 (5)	0.80973 (19)	0.23544 (8)	0.0153 (2)
C10	0.34956 (5)	0.6249 (2)	0.31680 (8)	0.0183 (2)
C11	0.40571 (5)	0.6100 (2)	0.39433 (9)	0.0214 (2)
C12	0.45582 (5)	0.7804 (2)	0.39679 (9)	0.0231 (2)
C13	0.44862 (5)	0.9614 (2)	0.32146 (9)	0.0214 (2)
C14	0.39083 (5)	0.9814 (2)	0.23836 (8)	0.0166 (2)
C15	0.38256 (5)	1.1693 (2)	0.16251 (8)	0.0181 (2)
C16	0.32655 (5)	1.19033 (19)	0.08122 (8)	0.0164 (2)
C17	0.31916 (5)	1.3816 (2)	0.00291 (9)	0.0201 (2)
C18	0.26502 (6)	1.3994 (2)	−0.07801 (9)	0.0218 (2)
C19	0.21559 (5)	1.2226 (2)	−0.08673 (8)	0.0209 (2)
C20	0.22049 (5)	1.0396 (2)	−0.01267 (8)	0.0183 (2)
C21	0.27525 (5)	1.01872 (19)	0.07639 (8)	0.0154 (2)
H6	0.1563 (7)	0.895 (3)	0.1471 (11)	0.021 (3)*
H7	0.2399 (6)	0.482 (3)	0.1653 (11)	0.019 (3)*
H10	0.3158 (7)	0.507 (3)	0.3176 (11)	0.024 (4)*
H11	0.4105 (8)	0.479 (3)	0.4498 (13)	0.035 (4)*
H12	0.4960 (7)	0.766 (3)	0.4544 (13)	0.033 (4)*
H13	0.4831 (8)	1.086 (3)	0.3216 (13)	0.032 (4)*
H15	0.4171 (7)	1.291 (3)	0.1670 (11)	0.024 (4)*
H17	0.3534 (7)	1.501 (3)	0.0097 (12)	0.027 (4)*
H18	0.2611 (8)	1.533 (3)	−0.1306 (13)	0.036 (4)*
H19	0.1780 (7)	1.232 (3)	−0.1469 (11)	0.025 (4)*
H20	0.1864 (7)	0.916 (3)	−0.0210 (11)	0.025 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0184 (4)	0.0134 (4)	0.0265 (4)	−0.0007 (3)	0.0020 (3)	0.0008 (3)
O2	0.0144 (3)	0.0166 (4)	0.0236 (4)	−0.0032 (3)	0.0031 (3)	0.0005 (3)
C1	0.0134 (5)	0.0248 (5)	0.0216 (5)	−0.0011 (4)	0.0031 (4)	0.0001 (4)
C2	0.0154 (5)	0.0222 (5)	0.0244 (5)	0.0021 (4)	0.0042 (4)	0.0002 (4)
C3	0.0165 (5)	0.0165 (5)	0.0196 (5)	−0.0007 (4)	0.0034 (4)	−0.0002 (4)
C4	0.0142 (4)	0.0148 (5)	0.0161 (4)	−0.0026 (4)	0.0027 (3)	0.0000 (3)
C5	0.0147 (4)	0.0143 (5)	0.0149 (4)	−0.0017 (3)	0.0016 (3)	−0.0006 (3)
C6	0.0161 (5)	0.0125 (4)	0.0199 (4)	−0.0013 (4)	0.0038 (4)	−0.0004 (4)
C7	0.0163 (5)	0.0139 (5)	0.0170 (4)	−0.0011 (4)	0.0030 (3)	−0.0004 (3)
C8	0.0136 (4)	0.0137 (4)	0.0175 (4)	−0.0003 (3)	0.0047 (3)	−0.0019 (3)
C9	0.0140 (4)	0.0155 (5)	0.0173 (4)	0.0008 (4)	0.0051 (3)	−0.0012 (4)
C10	0.0162 (5)	0.0180 (5)	0.0212 (5)	0.0012 (4)	0.0054 (4)	0.0007 (4)
C11	0.0190 (5)	0.0232 (5)	0.0219 (5)	0.0047 (4)	0.0049 (4)	0.0032 (4)
C12	0.0156 (5)	0.0286 (6)	0.0232 (5)	0.0024 (4)	0.0011 (4)	0.0001 (4)
C13	0.0139 (5)	0.0248 (6)	0.0245 (5)	−0.0009 (4)	0.0027 (4)	−0.0015 (4)
C14	0.0135 (4)	0.0177 (5)	0.0192 (4)	−0.0002 (4)	0.0050 (4)	−0.0026 (4)
C15	0.0157 (5)	0.0184 (5)	0.0213 (5)	−0.0025 (4)	0.0067 (4)	−0.0012 (4)
C16	0.0167 (5)	0.0153 (5)	0.0190 (4)	−0.0003 (4)	0.0075 (4)	−0.0014 (4)
C17	0.0217 (5)	0.0176 (5)	0.0234 (5)	−0.0010 (4)	0.0105 (4)	0.0013 (4)
C18	0.0259 (6)	0.0213 (5)	0.0207 (5)	0.0027 (4)	0.0106 (4)	0.0039 (4)
C19	0.0204 (5)	0.0243 (6)	0.0175 (5)	0.0024 (4)	0.0038 (4)	0.0011 (4)
C20	0.0170 (5)	0.0193 (5)	0.0184 (4)	−0.0003 (4)	0.0037 (4)	−0.0003 (4)
C21	0.0150 (4)	0.0149 (5)	0.0168 (4)	0.0006 (4)	0.0049 (3)	−0.0011 (4)

Geometric parameters (Å, º) top

O1—C5	1.2312 (13)	C10—H10	0.973 (15)
O2—C1	1.3606 (13)	C11—C12	1.4209 (17)
O2—C4	1.3754 (12)	C11—H11	0.997 (17)
C1—C2	1.3526 (16)	C12—C13	1.3642 (17)
C1—H1	0.981 (16)	C12—H12	0.996 (16)
C2—C3	1.4235 (15)	C13—C14	1.4342 (14)
C2—H2	0.968 (17)	C13—H13	1.007 (16)
C3—C4	1.3654 (14)	C14—C15	1.3950 (15)
C3—H3	0.974 (15)	C15—C16	1.3959 (14)
C4—C5	1.4609 (14)	C15—H15	0.988 (15)
C5—C6	1.4827 (14)	C16—C17	1.4310 (15)
C6—C7	1.3406 (14)	C16—C21	1.4396 (14)
C6—H6	0.941 (15)	C17—C18	1.3645 (16)
C7—C8	1.4757 (14)	C17—H17	0.972 (15)
C7—H7	1.009 (14)	C18—C19	1.4225 (17)
C8—C21	1.4176 (14)	C18—H18	0.984 (17)
C8—C9	1.4196 (14)	C19—C20	1.3653 (15)
C9—C10	1.4303 (14)	C19—H19	0.975 (14)
C9—C14	1.4353 (14)	C20—C21	1.4346 (14)
C10—C11	1.3701 (15)	C20—H20	0.984 (15)

C1—O2—C4	105.84 (8)	C10—C11—H11	118.7 (9)
C2—C1—O2	111.43 (10)	C12—C11—H11	120.6 (9)
C2—C1—H1	134.0 (9)	C13—C12—C11	120.23 (10)
O2—C1—H1	114.6 (9)	C13—C12—H12	120.8 (9)
C1—C2—C3	106.20 (10)	C11—C12—H12	119.0 (9)
C1—C2—H2	127.0 (10)	C12—C13—C14	120.72 (10)
C3—C2—H2	126.8 (10)	C12—C13—H13	122.1 (9)
C4—C3—C2	106.24 (9)	C14—C13—H13	117.2 (9)
C4—C3—H3	127.2 (9)	C15—C14—C13	121.04 (10)
C2—C3—H3	126.6 (9)	C15—C14—C9	119.63 (9)
C3—C4—O2	110.29 (9)	C13—C14—C9	119.30 (10)
C3—C4—C5	132.80 (9)	C14—C15—C16	121.51 (10)
O2—C4—C5	116.90 (9)	C14—C15—H15	119.0 (8)
O1—C5—C4	121.40 (9)	C16—C15—H15	119.5 (8)
O1—C5—C6	122.66 (9)	C15—C16—C17	120.89 (10)
C4—C5—C6	115.93 (9)	C15—C16—C21	119.67 (9)
C7—C6—C5	120.41 (10)	C17—C16—C21	119.43 (9)
C7—C6—H6	121.6 (9)	C18—C17—C16	121.01 (10)
C5—C6—H6	118.0 (9)	C18—C17—H17	120.7 (9)
C6—C7—C8	124.74 (10)	C16—C17—H17	118.3 (9)
C6—C7—H7	117.9 (8)	C17—C18—C19	119.86 (10)
C8—C7—H7	117.4 (8)	C17—C18—H18	119.4 (9)
C21—C8—C9	119.94 (9)	C19—C18—H18	120.8 (9)
C21—C8—C7	121.30 (9)	C20—C19—C18	120.81 (10)
C9—C8—C7	118.76 (9)	C20—C19—H19	120.0 (9)
C8—C9—C10	122.36 (9)	C18—C19—H19	119.2 (9)
C8—C9—C14	119.68 (9)	C19—C20—C21	121.48 (10)
C10—C9—C14	117.92 (9)	C19—C20—H20	119.7 (8)
C11—C10—C9	121.13 (10)	C21—C20—H20	118.8 (8)
C11—C10—H10	118.9 (8)	C8—C21—C20	123.23 (9)
C9—C10—H10	119.9 (8)	C8—C21—C16	119.46 (9)
C10—C11—C12	120.68 (10)	C20—C21—C16	117.25 (9)

C4—O2—C1—C2	0.05 (12)	C12—C13—C14—C15	178.54 (10)
O2—C1—C2—C3	0.07 (13)	C12—C13—C14—C9	0.46 (16)
C1—C2—C3—C4	−0.16 (12)	C8—C9—C14—C15	−0.25 (15)
C2—C3—C4—O2	0.20 (11)	C10—C9—C14—C15	−177.91 (9)
C2—C3—C4—C5	179.04 (10)	C8—C9—C14—C13	177.85 (9)
C1—O2—C4—C3	−0.16 (11)	C10—C9—C14—C13	0.20 (15)
C1—O2—C4—C5	−179.20 (8)	C13—C14—C15—C16	179.91 (10)
C3—C4—C5—O1	176.89 (11)	C9—C14—C15—C16	−2.01 (16)
O2—C4—C5—O1	−4.33 (14)	C14—C15—C16—C17	−178.97 (10)
C3—C4—C5—C6	−4.22 (16)	C14—C15—C16—C21	1.51 (15)
O2—C4—C5—C6	174.56 (8)	C15—C16—C17—C18	178.56 (10)
O1—C5—C6—C7	2.92 (15)	C21—C16—C17—C18	−1.92 (16)
C4—C5—C6—C7	−175.95 (9)	C16—C17—C18—C19	−1.51 (17)
C5—C6—C7—C8	178.00 (9)	C17—C18—C19—C20	2.45 (17)
C6—C7—C8—C21	−49.44 (15)	C18—C19—C20—C21	0.14 (17)
C6—C7—C8—C9	130.63 (11)	C9—C8—C21—C20	173.77 (9)
C21—C8—C9—C10	−179.46 (9)	C7—C8—C21—C20	−6.16 (15)
C7—C8—C9—C10	0.48 (15)	C9—C8—C21—C16	−3.49 (15)
C21—C8—C9—C14	2.99 (15)	C7—C8—C21—C16	176.57 (9)
C7—C8—C9—C14	−177.07 (9)	C19—C20—C21—C8	179.21 (10)
C8—C9—C10—C11	−178.45 (10)	C19—C20—C21—C16	−3.47 (15)
C14—C9—C10—C11	−0.86 (15)	C15—C16—C21—C8	1.27 (15)
C9—C10—C11—C12	0.87 (17)	C17—C16—C21—C8	−178.26 (9)
C10—C11—C12—C13	−0.18 (18)	C15—C16—C21—C20	−176.16 (9)
C11—C12—C13—C14	−0.48 (18)	C17—C16—C21—C20	4.31 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.98 (2)	2.34 (2)	3.2871 (14)	165 (1)
C6—H6···O1ⁱ	0.94 (2)	2.40 (2)	3.3366 (13)	173 (1)
C19—H19···O1ⁱⁱ	0.98 (1)	2.47 (1)	3.3419 (13)	148 (1)

Symmetry codes: (i) x, y+1, z; (ii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₄O₂
M_r	298.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	21.5743 (4), 5.4571 (1), 12.8394 (2)
β (°)	104.099 (1)
V (Å³)	1466.09 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.55 × 0.25 × 0.07

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.955, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	19468, 4251, 3549
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.118, 1.03
No. of reflections	4251
No. of parameters	264
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.22

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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
C3—H3···O1ⁱ	0.98 (2)	2.34 (2)	3.2871 (14)	165 (1)
C6—H6···O1ⁱ	0.94 (2)	2.40 (2)	3.3366 (13)	173 (1)
C19—H19···O1ⁱⁱ	0.98 (1)	2.47 (1)	3.3419 (13)	148 (1)

Symmetry codes: (i) x, y+1, z; (ii) x, −y+3/2, z−1/2.

Footnotes

†This paper is dedicated to His Majesty King Bhumibol Adulyadej of Thailand (King Rama IX) for his sustainable development of the country.

‡Thomson Reuters ResearcherID: A-5085-2009.

§Additional correspondence author, e-mail: hkfun@usm.my. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Thailand Research Fund (TRF) for research grant (RSA 5280033) and Prince of Songkla University for financial support. They also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

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