Redetermination of (E)-3-(anthracen-9-yl)-1-(2-hy­droxy­phen­yl)prop-2-en-1-one

Chantrapromma, S.; Kobkeatthawin, T.; Chanawanno, K.; Joothamongkhon, J.; Fun, H.-K.

doi:10.1107/S1600536811034994

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Pages o2554-o2555

https://doi.org/10.1107/S1600536811034994

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Redetermination of (E)-3-(anthracen-9-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one¹

Suchada Chantrapromma,^a ^*‡ Thawanrat Kobkeatthawin,^a Kullapa Chanawanno,^a Jaruwan Joothamongkhon ^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 4 July 2011; accepted 26 August 2011; online 3 September 2011)

The redetermined structure of title chalcone derivative, C₂₃H₁₆O₂, corrects errors in the title, scheme and synthesis in the previous report of the same structure [Jasinski et al. (2011 ). Acta Cryst. E67, o795]. There are two independent molecules in the asymmetric unit with slight differences in bond lengths and angles. The dihedral angle between the benzene ring and the anthracene ring system is 73.30 (4)° in one molecule and 73.18 (4)° in the other. Both molecules feature an intramolecular O—H⋯O hydrogen bond, which generates an S(6) ring. In the crystal, molecules are arranged into sheets lying parallel to the ac plane and further stacked along the b axis by π–π interactions with centroid–centroid distances in the range 3.6421 (6)–3.7607 (6) Å. The crystal structure is further stabilized by C—H⋯π interactions. There are also C⋯O [3.2159 (15) Å] short contacts.

Related literature

For the previous structure determination, see: Jasinski et al. (2011). For a related structure and background references, see: Joothamongkhon et al. (2010 ). For graph-set 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

C₂₃H₁₆O₂
M_r = 324.36
Monoclinic, P 2₁ /c
a = 14.0843 (2) Å
b = 13.7224 (2) Å
c = 16.9615 (3) Å
β = 101.411 (1)°
V = 3213.36 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.50 × 0.39 × 0.37 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.959, T_max = 0.969
40230 measured reflections
9368 independent reflections
7868 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.132
S = 1.02
9368 reflections
459 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg3, Cg5, Cg6 and Cg7 are the centroids of the C1A–C6A, C8A–C13A, C1B–C6B, C1B/C6B–C8B/C13B–C14B and C8B–C13B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2A—H1OA⋯O1A	0.93 (2)	1.69 (2)	2.5459 (12)	152.2 (19)
O2B—H1OB⋯O1B	0.88 (2)	1.75 (2)	2.5725 (13)	154.2 (19)
C5A—H5AA⋯Cg5	0.93	2.84	3.6754 (13)	151
C7A—H7AA⋯Cg6	0.93	2.76	3.6440 (12)	158
C9A—H9AA⋯Cg7	0.93	2.73	3.6325 (12)	164
C9B—H9BA⋯Cg1ⁱ	0.93	2.76	3.4023 (12)	127
C23B—H23B⋯Cg3	0.93	2.91	3.7661 (11)	154
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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: https://doi.org/10.1107/S1600536811034994/hb5945sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811034994/hb5945Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811034994/hb5945Isup3.cml

checkCIF report

Comment top

From our previous work, which revealed that a chalcone derivative containing the anthracene moiety displayed fluorescence (Joothamongkhon et al., 2010), the title compound (I) was synthesized by changing the substituent group on the phenyl ring for comparison of their properties. It was then discovered that a recent study of the same structure (Jasinski et al., 2011) contained errors in the title, scheme and synthesis. It was found that (I) exhibits fluorescence with the maximum emission at 438 nm when excited at 380 nm in chloroform solution. In addition our experiment shows that (I) also exhibits tyrosinase inhibitory activity with % inhibition of 12.882±8.511 at the concentration 0.125 mg ml^-1 when L-tyrosine was used as substrate.

The asymmetric unit of (I) contains two molecules, A and B, with the same configuration but with slight differences in bond lengths and angles. The molecule of (I) (Fig. 1) exists in an E configuration with respect to the C15═C16 double bond [1.3392 (15) Å in molecule A and 1.3370 (15) Å in molecule B] and the torsion angle C14–C15–C16–C17 = 177.64 (10)° in molecule A [-179.49 (10)° in molecule B]. The anthracene unit is essentially planar with the r.m.s. 0.0270 (1) Å for molecule A [0.0236 (1) Å for molecule B]. Atom O1 of the prop-2-en-1-one (C15–C17/O1) moiety is deviated from the propene plane with the torsion angle C15–C16–C17–O1 = 18.56 (16)° in molecule A [-17.28 (17)° in molecule B]. The total molecule is twisted as the dihedral angle between phenyl and anthracene rings is 73.70 (4)° and the mean through the pro-2-en-1-one unit makes the dihedral angles of 14.70 (7) and 61.46 (6)° with the phenyl and anthracene rings, respectively [the corresponding values are 73.18 (4), 11.04 (7) and 62.15 (6)° in molecule B]. Intramolecular O2A—H1OA···O1A and O2B—H1OB..O1B hydrogen bonds (Table 1) generate S(6) ring motifs (Bernstein et al., 1995).

The bond distances are comparable with those in the related structure noted above (Joothamongkhon et al., 2010).

In the crystal (Fig. 2), the molecules are arranged into sheets parallel to the ac plane and further stacked along the b axis by π–π interactions with the centroid···centroid distances: Cg₁···Cg₂ⁱⁱ = 3.6421 (6) Å; Cg₁···Cg₃ⁱⁱ = 3.6800 (7) Å; Cg₂···Cg₂ⁱⁱ = 3.7607 (6) Å; Cg₄···Cg₈ⁱⁱⁱ = 3.6434 (7) Å and Cg₅···Cg₆ⁱⁱ = 3.7084 (6) Å. The crystal structure is further stabilized by C—H···π interactions (Table 1); Cg₁, Cg₂, Cg₃, Cg₄, Cg₅, Cg₆, Cg₇ and Cg₈ are the centroids of C1A–C6A, C1A/C6A–C8A/C13A–C14A, C8A–C13A, C18A–C23A, C1B–C6B, C1B/C6B–C8B/C13B–C14B, C8B–C13B and C18B–C23B rings, respectively. C···Oⁱⁱⁱ[3.2159 (15) Å] short contacts were also observed [symmetry code: (iii) -x, -1/2 + y, 1/2 - z].

Related literature top

For the previous structure determination, see: Jasinski et al. (2011). For a related structure and background references, see: Joothamongkhon et al. (2010). For graph-set motifs, see: Bernstein et al. (1995). 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 (2 mmol, 0.41 g) with 2-hydroxyacetophenone (2 mmol, 0.27 g) in ethanol (40 ml) in the presence of NaOH(aq) (10 ml, 40%). After stirring for 4 hr at room temperature, a yellow solid appeared and was then collected by filtration, washed with distilled water and dried in air. Yellow blocks of (I) were recrystalized from acetone by the slow evaporation of the solvent at room temperature after several days, Mp. 431–432 K.

Structure description top

The bond distances are comparable with those in the related structure noted above (Joothamongkhon et al., 2010).

For the previous structure determination, see: Jasinski et al. (2011). For a related structure and background references, see: Joothamongkhon et al. (2010). For graph-set motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986).

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. O—H···O hydrogen bonds are shown as dashed lines.
	Fig. 2. The crystal packing of the title compound viewed along the b axis.

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

Crystal data top

C₂₃H₁₆O₂	F(000) = 1360
M_r = 324.36	D_x = 1.341 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 431–432 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.0843 (2) Å	Cell parameters from 9368 reflections
b = 13.7224 (2) Å	θ = 1.9–30.0°
c = 16.9615 (3) Å	µ = 0.09 mm⁻¹
β = 101.411 (1)°	T = 100 K
V = 3213.36 (9) Å³	Block, yellow
Z = 8	0.50 × 0.39 × 0.37 mm

Data collection top

Bruker APEXII CCD diffractometer	9368 independent reflections
Radiation source: sealed tube	7868 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
φ and ω scans	θ_max = 30.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −19→19
T_min = 0.959, T_max = 0.969	k = −17→19
40230 measured reflections	l = −23→23

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0739P)² + 1.125P] where P = (F_o² + 2F_c²)/3
9368 reflections	(Δ/σ)_max = 0.001
459 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₃H₁₆O₂	V = 3213.36 (9) Å³
M_r = 324.36	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.0843 (2) Å	µ = 0.09 mm⁻¹
b = 13.7224 (2) Å	T = 100 K
c = 16.9615 (3) Å	0.50 × 0.39 × 0.37 mm
β = 101.411 (1)°

Data collection top

Bruker APEXII CCD diffractometer	9368 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	7868 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.969	R_int = 0.032
40230 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.54 e Å⁻³
9368 reflections	Δρ_min = −0.21 e Å⁻³
459 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 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
O1A	0.23244 (6)	0.20731 (6)	0.25499 (5)	0.02242 (17)
O2A	0.12311 (6)	0.12104 (6)	0.13834 (5)	0.02449 (18)
C1A	0.44611 (8)	0.49417 (8)	0.37297 (6)	0.0174 (2)
C2A	0.50222 (8)	0.44622 (9)	0.32283 (6)	0.0227 (2)
H2AA	0.4773	0.3914	0.2936	0.027*
C3A	0.59212 (9)	0.48005 (11)	0.31737 (7)	0.0271 (3)
H3AA	0.6279	0.4475	0.2850	0.033*
C4A	0.63149 (9)	0.56412 (11)	0.36045 (7)	0.0279 (3)
H4AA	0.6923	0.5867	0.3556	0.033*
C5A	0.58036 (8)	0.61172 (9)	0.40878 (7)	0.0239 (2)
H5AA	0.6069	0.6666	0.4371	0.029*
C6A	0.48658 (8)	0.57869 (8)	0.41671 (6)	0.0185 (2)
C7A	0.43416 (8)	0.62652 (8)	0.46690 (7)	0.0194 (2)
H7AA	0.4608	0.6811	0.4955	0.023*
C8A	0.34265 (8)	0.59435 (8)	0.47522 (6)	0.0173 (2)
C9A	0.29196 (9)	0.64164 (8)	0.52973 (7)	0.0210 (2)
H9AA	0.3197	0.6953	0.5590	0.025*
C10A	0.20378 (9)	0.60920 (9)	0.53942 (7)	0.0231 (2)
H10A	0.1713	0.6412	0.5746	0.028*
C11A	0.16130 (8)	0.52659 (9)	0.49592 (7)	0.0217 (2)
H11A	0.1012	0.5045	0.5032	0.026*
C12A	0.20734 (8)	0.47903 (8)	0.44350 (6)	0.0188 (2)
H12A	0.1782	0.4248	0.4159	0.023*
C13A	0.29970 (8)	0.51123 (8)	0.43031 (6)	0.01584 (19)
C14A	0.35199 (8)	0.46226 (8)	0.37893 (6)	0.01602 (19)
C15A	0.31128 (8)	0.37739 (8)	0.33147 (6)	0.0184 (2)
H15A	0.3487	0.3211	0.3358	0.022*
C16A	0.22424 (8)	0.37492 (8)	0.28239 (6)	0.0199 (2)
H16A	0.1840	0.4292	0.2782	0.024*
C17A	0.19193 (8)	0.28682 (8)	0.23504 (6)	0.0179 (2)
C18A	0.11383 (8)	0.29411 (8)	0.16329 (6)	0.0172 (2)
C19A	0.08536 (8)	0.20943 (9)	0.11699 (6)	0.0193 (2)
C20A	0.01483 (9)	0.21635 (10)	0.04625 (7)	0.0242 (2)
H20A	−0.0024	0.1613	0.0147	0.029*
C21A	−0.02897 (9)	0.30437 (10)	0.02334 (7)	0.0252 (2)
H21A	−0.0761	0.3080	−0.0234	0.030*
C22A	−0.00370 (9)	0.38831 (9)	0.06921 (7)	0.0240 (2)
H22A	−0.0346	0.4472	0.0538	0.029*
C23A	0.06780 (8)	0.38290 (9)	0.13788 (7)	0.0209 (2)
H23A	0.0858	0.4390	0.1679	0.025*
O1B	0.18383 (6)	0.94230 (6)	0.26687 (5)	0.02468 (18)
O2B	0.03389 (7)	0.89265 (7)	0.16165 (5)	0.02348 (18)
C1B	0.50277 (8)	0.87960 (7)	0.47232 (6)	0.01604 (19)
C2B	0.53592 (8)	0.88359 (8)	0.39761 (6)	0.0194 (2)
H2BA	0.4912	0.8925	0.3499	0.023*
C3B	0.63166 (9)	0.87455 (9)	0.39523 (7)	0.0221 (2)
H3BA	0.6512	0.8783	0.3461	0.026*
C4B	0.70218 (9)	0.85953 (9)	0.46673 (7)	0.0223 (2)
H4BA	0.7673	0.8534	0.4641	0.027*
C5B	0.67406 (8)	0.85419 (8)	0.53925 (7)	0.0198 (2)
H5BA	0.7203	0.8442	0.5859	0.024*
C6B	0.57425 (8)	0.86375 (8)	0.54417 (6)	0.0166 (2)
C7B	0.54489 (8)	0.85640 (8)	0.61815 (6)	0.0173 (2)
H7BA	0.5912	0.8461	0.6647	0.021*
C8B	0.44772 (8)	0.86415 (8)	0.62337 (6)	0.0175 (2)
C9B	0.41872 (9)	0.85451 (9)	0.69944 (6)	0.0220 (2)
H9BA	0.4652	0.8414	0.7453	0.026*
C10B	0.32440 (9)	0.86416 (10)	0.70549 (7)	0.0253 (2)
H10B	0.3065	0.8564	0.7550	0.030*
C11B	0.25298 (9)	0.88619 (9)	0.63594 (7)	0.0233 (2)
H11B	0.1888	0.8945	0.6407	0.028*
C12B	0.27755 (8)	0.89535 (8)	0.56208 (7)	0.0196 (2)
H12B	0.2298	0.9104	0.5175	0.024*
C13B	0.37537 (8)	0.88220 (8)	0.55225 (6)	0.0165 (2)
C14B	0.40387 (8)	0.88795 (7)	0.47662 (6)	0.01590 (19)
C15B	0.33125 (8)	0.90127 (8)	0.40140 (6)	0.0180 (2)
H15B	0.3405	0.9525	0.3679	0.022*
C16B	0.25332 (8)	0.84486 (8)	0.37825 (6)	0.0189 (2)
H16B	0.2422	0.7934	0.4110	0.023*
C17B	0.18418 (8)	0.86241 (8)	0.30157 (6)	0.0181 (2)
C18B	0.11590 (8)	0.78474 (8)	0.26706 (6)	0.0167 (2)
C19B	0.04372 (8)	0.80431 (8)	0.19787 (6)	0.0184 (2)
C20B	−0.02191 (8)	0.73166 (9)	0.16524 (6)	0.0215 (2)
H20B	−0.0693	0.7450	0.1200	0.026*
C21B	−0.01681 (8)	0.64008 (9)	0.19984 (7)	0.0229 (2)
H21B	−0.0609	0.5922	0.1778	0.027*
C22B	0.05418 (9)	0.61899 (9)	0.26782 (7)	0.0217 (2)
H22B	0.0578	0.5572	0.2907	0.026*
C23B	0.11898 (8)	0.69067 (8)	0.30083 (6)	0.0190 (2)
H23B	0.1656	0.6765	0.3463	0.023*
H1OA	0.1696 (15)	0.1326 (15)	0.1845 (13)	0.052 (6)*
H1OB	0.0847 (15)	0.9246 (15)	0.1878 (12)	0.052 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0194 (4)	0.0219 (4)	0.0243 (4)	0.0023 (3)	0.0002 (3)	−0.0037 (3)
O2A	0.0203 (4)	0.0243 (4)	0.0272 (4)	0.0028 (3)	0.0006 (3)	−0.0089 (3)
C1A	0.0145 (5)	0.0220 (5)	0.0147 (4)	−0.0008 (4)	0.0008 (3)	0.0034 (4)
C2A	0.0185 (5)	0.0334 (6)	0.0157 (4)	0.0012 (4)	0.0021 (4)	0.0007 (4)
C3A	0.0182 (5)	0.0450 (8)	0.0187 (5)	0.0036 (5)	0.0048 (4)	0.0056 (5)
C4A	0.0159 (5)	0.0417 (7)	0.0254 (5)	−0.0036 (5)	0.0026 (4)	0.0124 (5)
C5A	0.0177 (5)	0.0273 (6)	0.0247 (5)	−0.0061 (4)	−0.0005 (4)	0.0094 (4)
C6A	0.0166 (5)	0.0195 (5)	0.0181 (4)	−0.0027 (4)	0.0004 (4)	0.0062 (4)
C7A	0.0206 (5)	0.0150 (5)	0.0209 (5)	−0.0032 (4)	−0.0001 (4)	0.0028 (4)
C8A	0.0187 (5)	0.0149 (5)	0.0173 (4)	0.0000 (4)	0.0011 (4)	0.0024 (3)
C9A	0.0255 (6)	0.0155 (5)	0.0210 (5)	0.0025 (4)	0.0023 (4)	−0.0006 (4)
C10A	0.0257 (6)	0.0226 (6)	0.0216 (5)	0.0057 (4)	0.0065 (4)	0.0009 (4)
C11A	0.0182 (5)	0.0245 (6)	0.0232 (5)	0.0006 (4)	0.0062 (4)	0.0034 (4)
C12A	0.0171 (5)	0.0193 (5)	0.0199 (5)	−0.0025 (4)	0.0030 (4)	0.0013 (4)
C13A	0.0159 (5)	0.0155 (5)	0.0154 (4)	−0.0003 (4)	0.0015 (3)	0.0019 (3)
C14A	0.0148 (5)	0.0178 (5)	0.0148 (4)	−0.0014 (4)	0.0013 (3)	0.0010 (3)
C15A	0.0176 (5)	0.0193 (5)	0.0182 (5)	−0.0005 (4)	0.0034 (4)	−0.0013 (4)
C16A	0.0194 (5)	0.0200 (5)	0.0192 (5)	0.0001 (4)	0.0016 (4)	−0.0035 (4)
C17A	0.0142 (5)	0.0221 (5)	0.0175 (4)	−0.0013 (4)	0.0037 (4)	−0.0028 (4)
C18A	0.0139 (5)	0.0222 (5)	0.0156 (4)	−0.0021 (4)	0.0036 (3)	−0.0017 (4)
C19A	0.0148 (5)	0.0242 (5)	0.0197 (5)	−0.0007 (4)	0.0055 (4)	−0.0046 (4)
C20A	0.0194 (5)	0.0319 (6)	0.0201 (5)	−0.0018 (5)	0.0012 (4)	−0.0084 (4)
C21A	0.0207 (5)	0.0365 (7)	0.0172 (5)	−0.0010 (5)	0.0010 (4)	−0.0010 (4)
C22A	0.0230 (6)	0.0274 (6)	0.0207 (5)	0.0000 (5)	0.0024 (4)	0.0045 (4)
C23A	0.0216 (5)	0.0221 (5)	0.0188 (5)	−0.0030 (4)	0.0032 (4)	0.0010 (4)
O1B	0.0254 (4)	0.0208 (4)	0.0249 (4)	−0.0021 (3)	−0.0021 (3)	0.0047 (3)
O2B	0.0221 (4)	0.0248 (4)	0.0214 (4)	0.0002 (3)	−0.0009 (3)	0.0023 (3)
C1B	0.0177 (5)	0.0129 (5)	0.0173 (4)	−0.0021 (4)	0.0028 (4)	−0.0009 (3)
C2B	0.0223 (5)	0.0185 (5)	0.0173 (5)	−0.0008 (4)	0.0038 (4)	0.0005 (4)
C3B	0.0242 (6)	0.0221 (5)	0.0217 (5)	−0.0015 (4)	0.0088 (4)	−0.0001 (4)
C4B	0.0179 (5)	0.0230 (6)	0.0273 (5)	−0.0004 (4)	0.0074 (4)	−0.0004 (4)
C5B	0.0165 (5)	0.0194 (5)	0.0228 (5)	−0.0003 (4)	0.0023 (4)	−0.0002 (4)
C6B	0.0173 (5)	0.0136 (5)	0.0186 (5)	−0.0009 (4)	0.0027 (4)	−0.0010 (3)
C7B	0.0179 (5)	0.0162 (5)	0.0169 (4)	−0.0013 (4)	0.0011 (4)	−0.0011 (3)
C8B	0.0195 (5)	0.0159 (5)	0.0169 (4)	−0.0029 (4)	0.0033 (4)	−0.0027 (3)
C9B	0.0234 (6)	0.0260 (6)	0.0163 (5)	−0.0046 (4)	0.0031 (4)	−0.0032 (4)
C10B	0.0254 (6)	0.0324 (6)	0.0193 (5)	−0.0059 (5)	0.0078 (4)	−0.0065 (4)
C11B	0.0183 (5)	0.0278 (6)	0.0249 (5)	−0.0035 (4)	0.0067 (4)	−0.0079 (4)
C12B	0.0177 (5)	0.0189 (5)	0.0219 (5)	−0.0018 (4)	0.0031 (4)	−0.0042 (4)
C13B	0.0172 (5)	0.0139 (5)	0.0180 (4)	−0.0020 (4)	0.0026 (4)	−0.0028 (3)
C14B	0.0170 (5)	0.0129 (5)	0.0171 (4)	−0.0015 (4)	0.0018 (4)	−0.0006 (3)
C15B	0.0193 (5)	0.0171 (5)	0.0172 (4)	0.0005 (4)	0.0023 (4)	0.0003 (4)
C16B	0.0188 (5)	0.0186 (5)	0.0182 (5)	−0.0012 (4)	0.0010 (4)	0.0013 (4)
C17B	0.0162 (5)	0.0194 (5)	0.0183 (4)	−0.0002 (4)	0.0026 (4)	−0.0006 (4)
C18B	0.0144 (5)	0.0203 (5)	0.0155 (4)	0.0000 (4)	0.0035 (3)	−0.0020 (4)
C19B	0.0164 (5)	0.0231 (5)	0.0164 (4)	0.0019 (4)	0.0046 (4)	−0.0015 (4)
C20B	0.0163 (5)	0.0305 (6)	0.0173 (5)	−0.0011 (4)	0.0028 (4)	−0.0052 (4)
C21B	0.0191 (5)	0.0264 (6)	0.0237 (5)	−0.0049 (4)	0.0057 (4)	−0.0081 (4)
C22B	0.0212 (5)	0.0208 (5)	0.0241 (5)	−0.0019 (4)	0.0069 (4)	−0.0028 (4)
C23B	0.0172 (5)	0.0216 (5)	0.0184 (5)	0.0002 (4)	0.0042 (4)	−0.0014 (4)

Geometric parameters (Å, º) top

O1A—C17A	1.2466 (14)	O1B—C17B	1.2438 (14)
O2A—C19A	1.3449 (14)	O2B—C19B	1.3537 (14)
O2A—H1OA	0.93 (2)	O2B—H1OB	0.88 (2)
C1A—C14A	1.4186 (14)	C1B—C14B	1.4138 (15)
C1A—C2A	1.4306 (15)	C1B—C6B	1.4354 (14)
C1A—C6A	1.4329 (16)	C1B—C2B	1.4356 (14)
C2A—C3A	1.3688 (17)	C2B—C3B	1.3627 (16)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.418 (2)	C3B—C4B	1.4224 (17)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.3606 (19)	C4B—C5B	1.3668 (15)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.4277 (15)	C5B—C6B	1.4307 (15)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.3962 (16)	C6B—C7B	1.4003 (14)
C7A—C8A	1.3957 (15)	C7B—C8B	1.3930 (15)
C7A—H7AA	0.9300	C7B—H7BA	0.9300
C8A—C9A	1.4306 (15)	C8B—C9B	1.4344 (14)
C8A—C13A	1.4371 (15)	C8B—C13B	1.4383 (15)
C9A—C10A	1.3595 (17)	C9B—C10B	1.3590 (17)
C9A—H9AA	0.9300	C9B—H9BA	0.9300
C10A—C11A	1.4187 (17)	C10B—C11B	1.4231 (17)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.3657 (15)	C11B—C12B	1.3699 (15)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.4327 (15)	C12B—C13B	1.4315 (15)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.4167 (14)	C13B—C14B	1.4200 (14)
C14A—C15A	1.4664 (15)	C14B—C15B	1.4802 (14)
C15A—C16A	1.3392 (15)	C15B—C16B	1.3370 (15)
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—C17A	1.4728 (15)	C16B—C17B	1.4821 (14)
C16A—H16A	0.9300	C16B—H16B	0.9300
C17A—C18A	1.4736 (14)	C17B—C18B	1.4767 (15)
C18A—C23A	1.4072 (16)	C18B—C23B	1.4095 (15)
C18A—C19A	1.4153 (15)	C18B—C19B	1.4179 (14)
C19A—C20A	1.4014 (15)	C19B—C20B	1.3972 (16)
C20A—C21A	1.3768 (18)	C20B—C21B	1.3828 (18)
C20A—H20A	0.9300	C20B—H20B	0.9300
C21A—C22A	1.3962 (17)	C21B—C22B	1.3989 (17)
C21A—H21A	0.9300	C21B—H21B	0.9300
C22A—C23A	1.3828 (16)	C22B—C23B	1.3827 (16)
C22A—H22A	0.9300	C22B—H22B	0.9300
C23A—H23A	0.9300	C23B—H23B	0.9300

C19A—O2A—H1OA	104.3 (13)	C19B—O2B—H1OB	102.6 (13)
C14A—C1A—C2A	122.30 (10)	C14B—C1B—C6B	120.07 (9)
C14A—C1A—C6A	119.63 (10)	C14B—C1B—C2B	122.56 (10)
C2A—C1A—C6A	118.04 (10)	C6B—C1B—C2B	117.34 (10)
C3A—C2A—C1A	120.75 (12)	C3B—C2B—C1B	121.28 (10)
C3A—C2A—H2AA	119.6	C3B—C2B—H2BA	119.4
C1A—C2A—H2AA	119.6	C1B—C2B—H2BA	119.4
C2A—C3A—C4A	120.91 (11)	C2B—C3B—C4B	121.07 (10)
C2A—C3A—H3AA	119.5	C2B—C3B—H3BA	119.5
C4A—C3A—H3AA	119.5	C4B—C3B—H3BA	119.5
C5A—C4A—C3A	120.09 (11)	C5B—C4B—C3B	119.82 (11)
C5A—C4A—H4AA	120.0	C5B—C4B—H4BA	120.1
C3A—C4A—H4AA	120.0	C3B—C4B—H4BA	120.1
C4A—C5A—C6A	120.94 (12)	C4B—C5B—C6B	120.71 (10)
C4A—C5A—H5AA	119.5	C4B—C5B—H5BA	119.6
C6A—C5A—H5AA	119.5	C6B—C5B—H5BA	119.6
C7A—C6A—C5A	121.26 (11)	C7B—C6B—C5B	120.89 (10)
C7A—C6A—C1A	119.48 (10)	C7B—C6B—C1B	119.33 (10)
C5A—C6A—C1A	119.26 (10)	C5B—C6B—C1B	119.77 (9)
C8A—C7A—C6A	121.55 (10)	C8B—C7B—C6B	121.30 (10)
C8A—C7A—H7AA	119.2	C8B—C7B—H7BA	119.4
C6A—C7A—H7AA	119.2	C6B—C7B—H7BA	119.4
C7A—C8A—C9A	120.72 (10)	C7B—C8B—C9B	120.55 (10)
C7A—C8A—C13A	119.85 (10)	C7B—C8B—C13B	120.12 (9)
C9A—C8A—C13A	119.41 (10)	C9B—C8B—C13B	119.33 (10)
C10A—C9A—C8A	120.95 (11)	C10B—C9B—C8B	121.02 (11)
C10A—C9A—H9AA	119.5	C10B—C9B—H9BA	119.5
C8A—C9A—H9AA	119.5	C8B—C9B—H9BA	119.5
C9A—C10A—C11A	120.00 (10)	C9B—C10B—C11B	119.96 (10)
C9A—C10A—H10A	120.0	C9B—C10B—H10B	120.0
C11A—C10A—H10A	120.0	C11B—C10B—H10B	120.0
C12A—C11A—C10A	120.98 (11)	C12B—C11B—C10B	120.83 (11)
C12A—C11A—H11A	119.5	C12B—C11B—H11B	119.6
C10A—C11A—H11A	119.5	C10B—C11B—H11B	119.6
C11A—C12A—C13A	121.14 (10)	C11B—C12B—C13B	121.21 (11)
C11A—C12A—H12A	119.4	C11B—C12B—H12B	119.4
C13A—C12A—H12A	119.4	C13B—C12B—H12B	119.4
C14A—C13A—C12A	123.25 (10)	C14B—C13B—C12B	123.29 (10)
C14A—C13A—C8A	119.15 (9)	C14B—C13B—C8B	119.16 (10)
C12A—C13A—C8A	117.51 (9)	C12B—C13B—C8B	117.54 (9)
C13A—C14A—C1A	120.29 (10)	C1B—C14B—C13B	119.97 (9)
C13A—C14A—C15A	121.33 (9)	C1B—C14B—C15B	119.04 (9)
C1A—C14A—C15A	118.38 (9)	C13B—C14B—C15B	120.98 (10)
C16A—C15A—C14A	124.87 (10)	C16B—C15B—C14B	124.67 (10)
C16A—C15A—H15A	117.6	C16B—C15B—H15B	117.7
C14A—C15A—H15A	117.6	C14B—C15B—H15B	117.7
C15A—C16A—C17A	120.39 (10)	C15B—C16B—C17B	121.49 (10)
C15A—C16A—H16A	119.8	C15B—C16B—H16B	119.3
C17A—C16A—H16A	119.8	C17B—C16B—H16B	119.3
O1A—C17A—C16A	119.67 (10)	O1B—C17B—C18B	120.49 (10)
O1A—C17A—C18A	120.69 (10)	O1B—C17B—C16B	119.92 (10)
C16A—C17A—C18A	119.62 (10)	C18B—C17B—C16B	119.59 (10)
C23A—C18A—C19A	118.57 (10)	C23B—C18B—C19B	117.98 (10)
C23A—C18A—C17A	122.35 (10)	C23B—C18B—C17B	122.32 (10)
C19A—C18A—C17A	119.07 (10)	C19B—C18B—C17B	119.70 (10)
O2A—C19A—C20A	117.85 (10)	O2B—C19B—C20B	117.32 (10)
O2A—C19A—C18A	122.52 (10)	O2B—C19B—C18B	122.50 (10)
C20A—C19A—C18A	119.63 (11)	C20B—C19B—C18B	120.17 (10)
C21A—C20A—C19A	120.22 (11)	C21B—C20B—C19B	120.36 (10)
C21A—C20A—H20A	119.9	C21B—C20B—H20B	119.8
C19A—C20A—H20A	119.9	C19B—C20B—H20B	119.8
C20A—C21A—C22A	121.06 (11)	C20B—C21B—C22B	120.44 (11)
C20A—C21A—H21A	119.5	C20B—C21B—H21B	119.8
C22A—C21A—H21A	119.5	C22B—C21B—H21B	119.8
C23A—C22A—C21A	119.21 (11)	C23B—C22B—C21B	119.57 (11)
C23A—C22A—H22A	120.4	C23B—C22B—H22B	120.2
C21A—C22A—H22A	120.4	C21B—C22B—H22B	120.2
C22A—C23A—C18A	121.27 (11)	C22B—C23B—C18B	121.48 (10)
C22A—C23A—H23A	119.4	C22B—C23B—H23B	119.3
C18A—C23A—H23A	119.4	C18B—C23B—H23B	119.3

C14A—C1A—C2A—C3A	178.79 (11)	C14B—C1B—C2B—C3B	−179.47 (10)
C6A—C1A—C2A—C3A	0.37 (16)	C6B—C1B—C2B—C3B	−1.22 (16)
C1A—C2A—C3A—C4A	−0.77 (18)	C1B—C2B—C3B—C4B	0.83 (18)
C2A—C3A—C4A—C5A	0.78 (18)	C2B—C3B—C4B—C5B	−0.13 (18)
C3A—C4A—C5A—C6A	−0.38 (17)	C3B—C4B—C5B—C6B	−0.13 (18)
C4A—C5A—C6A—C7A	179.27 (11)	C4B—C5B—C6B—C7B	178.72 (11)
C4A—C5A—C6A—C1A	−0.01 (16)	C4B—C5B—C6B—C1B	−0.31 (16)
C14A—C1A—C6A—C7A	2.27 (15)	C14B—C1B—C6B—C7B	0.20 (15)
C2A—C1A—C6A—C7A	−179.27 (10)	C2B—C1B—C6B—C7B	−178.10 (10)
C14A—C1A—C6A—C5A	−178.44 (10)	C14B—C1B—C6B—C5B	179.24 (10)
C2A—C1A—C6A—C5A	0.03 (15)	C2B—C1B—C6B—C5B	0.95 (15)
C5A—C6A—C7A—C8A	−179.69 (10)	C5B—C6B—C7B—C8B	−179.03 (10)
C1A—C6A—C7A—C8A	−0.41 (16)	C1B—C6B—C7B—C8B	0.01 (16)
C6A—C7A—C8A—C9A	177.12 (10)	C6B—C7B—C8B—C9B	178.75 (10)
C6A—C7A—C8A—C13A	−1.18 (16)	C6B—C7B—C8B—C13B	−1.40 (16)
C7A—C8A—C9A—C10A	−178.48 (10)	C7B—C8B—C9B—C10B	178.48 (11)
C13A—C8A—C9A—C10A	−0.17 (16)	C13B—C8B—C9B—C10B	−1.37 (17)
C8A—C9A—C10A—C11A	0.81 (17)	C8B—C9B—C10B—C11B	−1.32 (19)
C9A—C10A—C11A—C12A	−0.55 (17)	C9B—C10B—C11B—C12B	1.74 (19)
C10A—C11A—C12A—C13A	−0.37 (17)	C10B—C11B—C12B—C13B	0.62 (18)
C11A—C12A—C13A—C14A	177.54 (10)	C11B—C12B—C13B—C14B	177.98 (10)
C11A—C12A—C13A—C8A	0.98 (16)	C11B—C12B—C13B—C8B	−3.23 (16)
C7A—C8A—C13A—C14A	0.91 (15)	C7B—C8B—C13B—C14B	2.56 (15)
C9A—C8A—C13A—C14A	−177.41 (10)	C9B—C8B—C13B—C14B	−177.58 (10)
C7A—C8A—C13A—C12A	177.61 (10)	C7B—C8B—C13B—C12B	−176.28 (10)
C9A—C8A—C13A—C12A	−0.71 (15)	C9B—C8B—C13B—C12B	3.57 (15)
C12A—C13A—C14A—C1A	−175.56 (10)	C6B—C1B—C14B—C13B	1.00 (15)
C8A—C13A—C14A—C1A	0.95 (15)	C2B—C1B—C14B—C13B	179.20 (10)
C12A—C13A—C14A—C15A	3.81 (16)	C6B—C1B—C14B—C15B	−178.15 (9)
C8A—C13A—C14A—C15A	−179.68 (9)	C2B—C1B—C14B—C15B	0.05 (16)
C2A—C1A—C14A—C13A	179.07 (10)	C12B—C13B—C14B—C1B	176.41 (10)
C6A—C1A—C14A—C13A	−2.53 (15)	C8B—C13B—C14B—C1B	−2.36 (15)
C2A—C1A—C14A—C15A	−0.31 (15)	C12B—C13B—C14B—C15B	−4.45 (16)
C6A—C1A—C14A—C15A	178.08 (9)	C8B—C13B—C14B—C15B	176.78 (10)
C13A—C14A—C15A—C16A	52.54 (15)	C1B—C14B—C15B—C16B	125.91 (12)
C1A—C14A—C15A—C16A	−128.08 (12)	C13B—C14B—C15B—C16B	−53.23 (16)
C14A—C15A—C16A—C17A	177.64 (10)	C14B—C15B—C16B—C17B	−179.49 (10)
C15A—C16A—C17A—O1A	18.56 (16)	C15B—C16B—C17B—O1B	−17.28 (17)
C15A—C16A—C17A—C18A	−159.78 (10)	C15B—C16B—C17B—C18B	162.91 (10)
O1A—C17A—C18A—C23A	−178.62 (10)	O1B—C17B—C18B—C23B	174.78 (10)
C16A—C17A—C18A—C23A	−0.30 (15)	C16B—C17B—C18B—C23B	−5.41 (15)
O1A—C17A—C18A—C19A	−0.13 (15)	O1B—C17B—C18B—C19B	−5.71 (16)
C16A—C17A—C18A—C19A	178.20 (9)	C16B—C17B—C18B—C19B	174.10 (9)
C23A—C18A—C19A—O2A	−177.65 (10)	C23B—C18B—C19B—O2B	179.06 (9)
C17A—C18A—C19A—O2A	3.80 (15)	C17B—C18B—C19B—O2B	−0.47 (15)
C23A—C18A—C19A—C20A	1.96 (15)	C23B—C18B—C19B—C20B	0.22 (15)
C17A—C18A—C19A—C20A	−176.59 (10)	C17B—C18B—C19B—C20B	−179.31 (10)
O2A—C19A—C20A—C21A	177.39 (11)	O2B—C19B—C20B—C21B	−179.19 (10)
C18A—C19A—C20A—C21A	−2.24 (17)	C18B—C19B—C20B—C21B	−0.28 (16)
C19A—C20A—C21A—C22A	0.64 (18)	C19B—C20B—C21B—C22B	−0.11 (17)
C20A—C21A—C22A—C23A	1.23 (18)	C20B—C21B—C22B—C23B	0.56 (17)
C21A—C22A—C23A—C18A	−1.48 (17)	C21B—C22B—C23B—C18B	−0.63 (16)
C19A—C18A—C23A—C22A	−0.11 (16)	C19B—C18B—C23B—C22B	0.24 (15)
C17A—C18A—C23A—C22A	178.39 (10)	C17B—C18B—C23B—C22B	179.76 (10)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg3, Cg5, Cg6 and Cg7 are the centroids of the C1A–C6A, C8A–C13A, C1B–C6B, C1B/C6B–C8B/C13B–C14B and C8B–C13B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H1OA···O1A	0.93 (2)	1.69 (2)	2.5459 (12)	152.2 (19)
O2B—H1OB···O1B	0.88 (2)	1.75 (2)	2.5725 (13)	154.2 (19)
C5A—H5AA···Cg5	0.93	2.84	3.6754 (13)	151
C7A—H7AA···Cg6	0.93	2.76	3.6440 (12)	158
C9A—H9AA···Cg7	0.93	2.73	3.6325 (12)	164
C9B—H9BA···Cg1ⁱ	0.93	2.76	3.4023 (12)	127
C23B—H23B···Cg3	0.93	2.91	3.7661 (11)	154

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₆O₂
M_r	324.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	14.0843 (2), 13.7224 (2), 16.9615 (3)
β (°)	101.411 (1)
V (Å³)	3213.36 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.39 × 0.37

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.959, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	40230, 9368, 7868
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.132, 1.02
No. of reflections	9368
No. of parameters	459
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.21

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1, Cg3, Cg5, Cg6 and Cg7 are the centroids of the C1A–C6A, C8A–C13A, C1B–C6B, C1B/C6B–C8B/C13B–C14B and C8B–C13B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H1OA···O1A	0.93 (2)	1.69 (2)	2.5459 (12)	152.2 (19)
O2B—H1OB···O1B	0.88 (2)	1.75 (2)	2.5725 (13)	154.2 (19)
C5A—H5AA···Cg5	0.93	2.84	3.6754 (13)	151
C7A—H7AA···Cg6	0.93	2.76	3.6440 (12)	158
C9A—H9AA···Cg7	0.93	2.73	3.6325 (12)	164
C9B—H9BA···Cg1ⁱ	0.93	2.76	3.4023 (12)	127
C23B—H23B···Cg3	0.93	2.91	3.7661 (11)	154

Symmetry code: (i) x, −y+1/2, z−1/2.

Footnotes

¹This paper is dedicated to Her Royal Highness Princess Chulabhorn Walailak of Thailand for her contributions to science on the occasion of her 54th birthday, which fell on July 4th, 2011.

‡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 a research grant (RSA 5280033) and the Prince of Songkla University for financial support. The authors also thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

References

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 (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals 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
Joothamongkhon, J., Chantrapromma, S., Kobkeatthawin, T. & Fun, H.-K. (2010). Acta Cryst. E66, o2669–o2670. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals 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 10| October 2011| Pages o2554-o2555

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Redetermination of (E)-3-(anthracen-9-yl)-1-(2-hy­dr­oxy­phen­yl)prop-2-en-1-one1

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Redetermination of (E)-3-(anthracen-9-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one¹