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

Suchada Chantrapromma; Thawanrat Kobkeatthawin; Kullapa Chanawanno; Jaruwan Joothamongkhon; Hoong-Kun Fun

doi:10.1107/S1600536811034994

. 2011 Sep 3;67(Pt 10):o2554–o2555. doi: 10.1107/S1600536811034994

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, Hoong-Kun Fun ^b,^§

PMCID: PMC3201364 PMID: 22065671

Abstract

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,
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[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 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

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 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811034994/hb5945sup1.cif

e-67-o2554-sup1.cif^{(31.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034994/hb5945Isup2.hkl

e-67-o2554-Isup2.hkl^{(458.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811034994/hb5945Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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Symmetry code: (i) Inline graphic .

Acknowledgments

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.

supplementary crystallographic information

Comment

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].

Experimental

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.