(Z)-3-(9-Anthr­yl)-1-(4-methoxy­phen­yl)prop-2-en-1-one

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

doi:10.1107/S1600536809038665

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 11| November 2009| Pages o2673-o2674

https://doi.org/10.1107/S1600536809038665

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(Z)-3-(9-Anthryl)-1-(4-methoxyphenyl)prop-2-en-1-one¹

Suchada Chantrapromma,^a ^*‡ Jirapa Horkaew,^a Thitipone Suwunwong ^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 19 September 2009; accepted 24 September 2009; online 10 October 2009)

The title chalcone derivative, C₂₄H₁₈O₂, which consists of the substituted 4-methoxyphenyl and anthracene rings bridged by the prop-2-en-1-one unit, exists in a cis configuration. The molecule is twisted, the interplanar angle between the benzene and anthracene rings being 69.50 (10)°. The methoxy group is coplanar with the attached benzene ring [C—O—C—C angle = 2.9 (3)°]. In the crystal structure, molecules are linked into chains along the a axis by a weak C—H⋯O(enone) interaction. The chains are stacked along the c axis. A C—H⋯π interaction involving the benzene ring is observed.

Related literature

For bond-length data, see: Allen et al. (1987 ). For related structures, see: Fun et al. (2009 ); Suwunwong et al. (2009 ). For background to and applications of chalcones, see: Patil & Dharmaprakash (2008 ); Saydam et al. (2003 ); Svetlichny et al. (2007 ). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ).

Experimental

Crystal data

C₂₄H₁₈O₂
M_r = 338.38
Monoclinic, C c
a = 5.5018 (2) Å
b = 19.9215 (8) Å
c = 16.0500 (7) Å
β = 95.072 (2)°
V = 1752.26 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.54 × 0.27 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.958, T_max = 0.993
7966 measured reflections
1721 independent reflections
1545 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.087
S = 1.07
1721 reflections
236 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1ⁱ	0.93	2.47	3.290 (3)	147
C24—H24A⋯O1ⁱⁱ	0.96	2.59	3.176 (4)	120
C17—H17A⋯Cg1ⁱⁱⁱ	0.93	2.89	3.694 (3)	145
Symmetry codes: (i) x-1, y, z; (ii) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ . Cg1 is the centroid of the C1–C6 ring.

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/S1600536809038665/sj2659sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809038665/sj2659Isup2.hkl

checkCIF report

Comment top

Chalcones have been studied for their wide range of applications such as non-linear optical (Patil & Dharmaprakash, 2008) and fluorescent properties (Svetlichny et al., 2007) and biological activities (Saydam et al., 2003). We have previously reported crystal structures of chalcone derivatives containing the anthracene moiety which exist in both the E (Suwunwong et al., 2009) and Z configurations (Fun et al., 2009). The title compound was synthesized to study its fluorescent properties in addition to its antibacterial activity. The title compound shows interesting fluorescence properties which will be reported elsewhere. The crystal structure of the title compound was studied in order to elucidate its conformation which may affect the fluorescence properties.

The molecule of the title chalcone derivative, C₂₄H₁₈O₂, (Fig. 1) exists in a Z configuration with respect to the C8=C9 ethenyl bond with the torsion angle C7–C8–C9–C10 being 3.6 (5)°. The anthracene ring system (C10–C23) is essentially planar with the root mean deviation of 0.050 (3) Å. The molecule is twisted as shown by the interplanar angle between the 4-methoxyphenyl and anthracene rings being 69.50 (10)°. The substituted methoxy group is coplanar with the phenyl ring with the torsion angle C24–O2–C3–C2 being 2.9 (3)°. The prop-2-en-1-one unit (C7—C9/O1) is twisted with the torsion angle O1–C7–C8–C9 of 44.5 (4)°. The orientation of the prop-2-en-1-one unit with respect to the 4-methoxyphenyl and anthracene rings is indicated by the torsion angles C1–C6–C7–C8 = 15.6 (4) and C7–C8–C9–C10 = 3.6 (5) °. The bond distances (Allen et al., 1987) and angles are normal and comparable to those found in closely related structures (Fun et al., 2009; Suwunwong et al., 2009).

In the crystal packing, the molecules are linked into chains along the a axis through the enone unit by a weak C8—H8A···O1 interaction (Fig. 2, Table 1). These chains are stacked along the c axis involving a C—H···π interaction (Table 1); Cg₁ is the centroid of the C1–C6 ring.

Related literature top

For bond-length data, see: Allen et al. (1987). For related structures, see: Fun et al. (2009); Suwunwong et al. (2009). For background to and applications of chalcones, see: Patil & Dharmaprakash (2008); Saydam et al. (2003); Svetlichny et al. (2007). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986). Cg1 is the centroid of the C1–C6 ring.

Experimental top

The title compound was synthesized by condensation of anthracene-9-carbaldehyde (0.41 g, 2 mmol) with 4-methoxyacetophenone (0.30 g, 2 mmol) in ethanol (30 ml) in the presence of 30% aqueous NaOH (5 ml) at room temperature. After stirring for 3 hr, a yellow solid appeared and was then collected by filtration, washed with acetone and dried in air. Yellow block-shaped single crystals of the title compound suitable for x-ray structure determination were recrystalized from ethanol by the slow evaporation of the solvent at room temperature after several days, Mp. 440–441 K.

Structure description top

For bond-length data, see: Allen et al. (1987). For related structures, see: Fun et al. (2009); Suwunwong et al. (2009). For background to and applications of chalcones, see: Patil & Dharmaprakash (2008); Saydam et al. (2003); Svetlichny et al. (2007). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986). Cg1 is the centroid of the C1–C6 ring.

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, showing chains running along the a axis. Weak C—H···O interactions are shown as dashed lines.

(Z)-3-(9-Anthryl)-1-(4-methoxyphenyl)prop-2-en-1-one top

Crystal data top

C₂₄H₁₈O₂	F(000) = 712
M_r = 338.38	D_x = 1.283 Mg m⁻³
Monoclinic, Cc	Melting point = 440–441 K
Hall symbol: C -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 5.5018 (2) Å	Cell parameters from 1721 reflections
b = 19.9215 (8) Å	θ = 2.0–26.0°
c = 16.0500 (7) Å	µ = 0.08 mm⁻¹
β = 95.072 (2)°	T = 293 K
V = 1752.26 (12) Å³	Plate, yellow
Z = 4	0.54 × 0.27 × 0.09 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1721 independent reflections
Radiation source: fine-focus sealed tube	1545 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 8.33 pixels mm^-1	θ_max = 26.0°, θ_min = 2.0°
ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −24→23
T_min = 0.958, T_max = 0.993	l = −19→19
7966 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0414P)² + 0.4575P] where P = (F_o² + 2F_c²)/3
1721 reflections	(Δ/σ)_max = 0.001
236 parameters	Δρ_max = 0.14 e Å⁻³
2 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₄H₁₈O₂	V = 1752.26 (12) Å³
M_r = 338.38	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 5.5018 (2) Å	µ = 0.08 mm⁻¹
b = 19.9215 (8) Å	T = 293 K
c = 16.0500 (7) Å	0.54 × 0.27 × 0.09 mm
β = 95.072 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1721 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1545 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.993	R_int = 0.023
7966 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	2 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.07	Δρ_max = 0.14 e Å⁻³
1721 reflections	Δρ_min = −0.14 e Å⁻³
236 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	0.7379 (3)	0.26049 (10)	0.44324 (14)	0.0584 (5)
O2	0.5958 (4)	−0.04663 (10)	0.52663 (15)	0.0663 (6)
C1	0.3633 (5)	0.11209 (14)	0.43620 (17)	0.0469 (7)
H1A	0.2261	0.1294	0.4055	0.056*
C2	0.3691 (5)	0.04454 (15)	0.45676 (18)	0.0514 (7)
H2A	0.2382	0.0169	0.4394	0.062*
C3	0.5709 (5)	0.01859 (14)	0.50326 (17)	0.0469 (6)
C4	0.7641 (5)	0.06087 (14)	0.52870 (18)	0.0498 (7)
H4A	0.8992	0.0437	0.5607	0.060*
C5	0.7586 (4)	0.12742 (14)	0.50729 (17)	0.0448 (6)
H5A	0.8907	0.1548	0.5243	0.054*
C6	0.5565 (4)	0.15470 (13)	0.46010 (15)	0.0394 (6)
C7	0.5525 (4)	0.22645 (13)	0.43565 (16)	0.0413 (6)
C8	0.3147 (4)	0.25664 (13)	0.40406 (18)	0.0454 (6)
H8A	0.1795	0.2456	0.4322	0.054*
C9	0.2783 (5)	0.29786 (13)	0.33936 (17)	0.0451 (6)
H9A	0.1214	0.3150	0.3286	0.054*
C10	0.4614 (4)	0.31959 (13)	0.28220 (16)	0.0411 (6)
C11	0.5862 (5)	0.27224 (13)	0.23652 (16)	0.0428 (6)
C12	0.5348 (6)	0.20192 (15)	0.23660 (18)	0.0527 (7)
H12A	0.4126	0.1859	0.2678	0.063*
C13	0.6601 (6)	0.15829 (16)	0.1923 (2)	0.0634 (9)
H13A	0.6205	0.1129	0.1927	0.076*
C14	0.8495 (7)	0.18016 (18)	0.1455 (2)	0.0670 (9)
H14A	0.9371	0.1492	0.1167	0.080*
C15	0.9040 (6)	0.24607 (17)	0.14224 (18)	0.0580 (8)
H15A	1.0296	0.2601	0.1112	0.070*
C16	0.7721 (5)	0.29480 (14)	0.18577 (15)	0.0460 (6)
C17	0.8194 (5)	0.36309 (15)	0.17973 (16)	0.0491 (7)
H17A	0.9427	0.3773	0.1478	0.059*
C18	0.6874 (5)	0.41081 (14)	0.22015 (16)	0.0463 (7)
C19	0.7276 (6)	0.48094 (15)	0.21182 (19)	0.0559 (8)
H19A	0.8496	0.4957	0.1796	0.067*
C20	0.5933 (6)	0.52656 (16)	0.2495 (2)	0.0622 (8)
H20A	0.6211	0.5721	0.2422	0.075*
C21	0.4106 (6)	0.50528 (17)	0.2999 (2)	0.0616 (8)
H21A	0.3169	0.5370	0.3251	0.074*
C22	0.3704 (5)	0.43918 (16)	0.31209 (18)	0.0529 (7)
H22A	0.2533	0.4263	0.3473	0.063*
C23	0.5028 (5)	0.38878 (13)	0.27229 (16)	0.0426 (6)
C24	0.4045 (7)	−0.09228 (16)	0.4985 (3)	0.0761 (10)
H24A	0.4477	−0.1368	0.5173	0.114*
H24B	0.3820	−0.0916	0.4385	0.114*
H24C	0.2557	−0.0790	0.5209	0.114*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0426 (10)	0.0571 (12)	0.0750 (14)	−0.0105 (10)	0.0021 (9)	0.0098 (11)
O2	0.0777 (15)	0.0442 (12)	0.0741 (15)	−0.0021 (11)	−0.0085 (12)	0.0055 (11)
C1	0.0362 (13)	0.0538 (17)	0.0499 (15)	−0.0038 (12)	−0.0007 (11)	0.0081 (13)
C2	0.0466 (15)	0.0532 (17)	0.0532 (16)	−0.0111 (13)	−0.0017 (13)	0.0015 (13)
C3	0.0513 (15)	0.0464 (16)	0.0435 (15)	0.0022 (12)	0.0071 (12)	0.0015 (12)
C4	0.0450 (15)	0.0519 (17)	0.0514 (16)	0.0072 (13)	−0.0026 (12)	0.0011 (13)
C5	0.0340 (13)	0.0535 (16)	0.0471 (15)	−0.0037 (12)	0.0041 (11)	−0.0032 (12)
C6	0.0337 (12)	0.0493 (16)	0.0365 (13)	−0.0027 (11)	0.0101 (10)	0.0015 (11)
C7	0.0372 (13)	0.0498 (15)	0.0387 (13)	−0.0049 (12)	0.0132 (11)	0.0020 (12)
C8	0.0357 (13)	0.0479 (15)	0.0543 (16)	−0.0020 (12)	0.0133 (11)	0.0064 (13)
C9	0.0363 (13)	0.0449 (16)	0.0542 (15)	0.0019 (11)	0.0042 (11)	0.0035 (13)
C10	0.0381 (13)	0.0470 (16)	0.0377 (13)	−0.0006 (11)	−0.0003 (10)	0.0045 (11)
C11	0.0459 (14)	0.0439 (15)	0.0376 (13)	0.0007 (11)	−0.0018 (11)	0.0044 (12)
C12	0.0589 (17)	0.0486 (16)	0.0505 (16)	−0.0023 (14)	0.0040 (14)	0.0033 (14)
C13	0.084 (2)	0.0470 (17)	0.0592 (18)	0.0052 (16)	0.0048 (17)	−0.0025 (15)
C14	0.084 (2)	0.063 (2)	0.0557 (18)	0.0208 (18)	0.0146 (17)	−0.0049 (16)
C15	0.0646 (19)	0.068 (2)	0.0430 (16)	0.0071 (16)	0.0165 (14)	0.0037 (14)
C16	0.0495 (16)	0.0547 (17)	0.0335 (13)	0.0020 (13)	0.0015 (11)	0.0041 (12)
C17	0.0483 (15)	0.0615 (19)	0.0384 (14)	−0.0058 (13)	0.0083 (12)	0.0093 (13)
C18	0.0499 (15)	0.0505 (17)	0.0370 (13)	−0.0056 (13)	−0.0043 (12)	0.0073 (12)
C19	0.0635 (19)	0.0537 (19)	0.0496 (16)	−0.0158 (15)	0.0000 (14)	0.0084 (14)
C20	0.079 (2)	0.0415 (17)	0.063 (2)	−0.0042 (16)	−0.0104 (17)	0.0035 (15)
C21	0.070 (2)	0.0494 (19)	0.0640 (19)	0.0076 (15)	−0.0005 (16)	−0.0029 (15)
C22	0.0531 (16)	0.0531 (19)	0.0520 (17)	0.0021 (14)	0.0027 (13)	0.0015 (14)
C23	0.0438 (14)	0.0436 (15)	0.0390 (13)	−0.0005 (12)	−0.0037 (11)	0.0029 (11)
C24	0.093 (3)	0.052 (2)	0.082 (2)	−0.0170 (18)	−0.003 (2)	0.0025 (18)

Geometric parameters (Å, º) top

O1—C7	1.222 (3)	C12—H12A	0.9300
O2—C3	1.356 (3)	C13—C14	1.407 (5)
O2—C24	1.433 (4)	C13—H13A	0.9300
C1—C2	1.385 (4)	C14—C15	1.349 (5)
C1—C6	1.387 (4)	C14—H14A	0.9300
C1—H1A	0.9300	C15—C16	1.431 (4)
C2—C3	1.382 (4)	C15—H15A	0.9300
C2—H2A	0.9300	C16—C17	1.390 (4)
C3—C4	1.389 (4)	C17—C18	1.391 (4)
C4—C5	1.369 (4)	C17—H17A	0.9300
C4—H4A	0.9300	C18—C19	1.423 (4)
C5—C6	1.399 (4)	C18—C23	1.440 (4)
C5—H5A	0.9300	C19—C20	1.348 (5)
C6—C7	1.482 (4)	C19—H19A	0.9300
C7—C8	1.488 (4)	C20—C21	1.411 (5)
C8—C9	1.325 (4)	C20—H20A	0.9300
C8—H8A	0.9300	C21—C22	1.352 (5)
C9—C10	1.486 (4)	C21—H21A	0.9300
C9—H9A	0.9300	C22—C23	1.425 (4)
C10—C23	1.408 (4)	C22—H22A	0.9300
C10—C11	1.410 (4)	C24—H24A	0.9600
C11—C12	1.429 (4)	C24—H24B	0.9600
C11—C16	1.435 (4)	C24—H24C	0.9600
C12—C13	1.350 (4)

C3—O2—C24	117.9 (2)	C12—C13—H13A	119.4
C2—C1—C6	121.8 (3)	C14—C13—H13A	119.4
C2—C1—H1A	119.1	C15—C14—C13	120.0 (3)
C6—C1—H1A	119.1	C15—C14—H14A	120.0
C3—C2—C1	119.5 (3)	C13—C14—H14A	120.0
C3—C2—H2A	120.2	C14—C15—C16	121.2 (3)
C1—C2—H2A	120.2	C14—C15—H15A	119.4
O2—C3—C2	124.4 (3)	C16—C15—H15A	119.4
O2—C3—C4	116.4 (2)	C17—C16—C15	121.6 (3)
C2—C3—C4	119.3 (3)	C17—C16—C11	119.5 (2)
C5—C4—C3	120.9 (2)	C15—C16—C11	118.9 (3)
C5—C4—H4A	119.5	C16—C17—C18	121.9 (2)
C3—C4—H4A	119.5	C16—C17—H17A	119.1
C4—C5—C6	120.7 (2)	C18—C17—H17A	119.1
C4—C5—H5A	119.6	C17—C18—C19	122.4 (3)
C6—C5—H5A	119.6	C17—C18—C23	119.1 (2)
C1—C6—C5	117.7 (2)	C19—C18—C23	118.5 (3)
C1—C6—C7	121.6 (2)	C20—C19—C18	121.6 (3)
C5—C6—C7	120.7 (2)	C20—C19—H19A	119.2
O1—C7—C6	121.1 (2)	C18—C19—H19A	119.2
O1—C7—C8	120.7 (2)	C19—C20—C21	120.1 (3)
C6—C7—C8	118.2 (2)	C19—C20—H20A	119.9
C9—C8—C7	125.8 (2)	C21—C20—H20A	119.9
C9—C8—H8A	117.1	C22—C21—C20	120.6 (3)
C7—C8—H8A	117.1	C22—C21—H21A	119.7
C8—C9—C10	126.9 (2)	C20—C21—H21A	119.7
C8—C9—H9A	116.5	C21—C22—C23	121.7 (3)
C10—C9—H9A	116.5	C21—C22—H22A	119.2
C23—C10—C11	120.3 (2)	C23—C22—H22A	119.2
C23—C10—C9	118.7 (2)	C10—C23—C22	123.0 (2)
C11—C10—C9	120.9 (2)	C10—C23—C18	119.6 (2)
C10—C11—C12	123.4 (2)	C22—C23—C18	117.4 (2)
C10—C11—C16	119.3 (2)	O2—C24—H24A	109.5
C12—C11—C16	117.3 (2)	O2—C24—H24B	109.5
C13—C12—C11	121.4 (3)	H24A—C24—H24B	109.5
C13—C12—H12A	119.3	O2—C24—H24C	109.5
C11—C12—H12A	119.3	H24A—C24—H24C	109.5
C12—C13—C14	121.2 (3)	H24B—C24—H24C	109.5

C6—C1—C2—C3	0.8 (4)	C12—C13—C14—C15	−2.0 (5)
C24—O2—C3—C2	2.6 (4)	C13—C14—C15—C16	0.0 (5)
C24—O2—C3—C4	−177.4 (3)	C14—C15—C16—C17	−177.0 (3)
C1—C2—C3—O2	−179.8 (3)	C14—C15—C16—C11	2.8 (4)
C1—C2—C3—C4	0.1 (4)	C10—C11—C16—C17	−2.6 (4)
O2—C3—C4—C5	179.0 (3)	C12—C11—C16—C17	176.3 (2)
C2—C3—C4—C5	−1.0 (4)	C10—C11—C16—C15	177.6 (2)
C3—C4—C5—C6	0.8 (4)	C12—C11—C16—C15	−3.4 (3)
C2—C1—C6—C5	−1.0 (4)	C15—C16—C17—C18	178.3 (2)
C2—C1—C6—C7	178.0 (2)	C11—C16—C17—C18	−1.5 (4)
C4—C5—C6—C1	0.1 (4)	C16—C17—C18—C19	−177.5 (3)
C4—C5—C6—C7	−178.9 (2)	C16—C17—C18—C23	2.4 (4)
C1—C6—C7—O1	−166.3 (3)	C17—C18—C19—C20	178.0 (3)
C5—C6—C7—O1	12.6 (4)	C23—C18—C19—C20	−1.8 (4)
C1—C6—C7—C8	15.6 (4)	C18—C19—C20—C21	1.2 (5)
C5—C6—C7—C8	−165.4 (2)	C19—C20—C21—C22	0.9 (5)
O1—C7—C8—C9	44.5 (4)	C20—C21—C22—C23	−2.5 (5)
C6—C7—C8—C9	−137.5 (3)	C11—C10—C23—C22	175.5 (2)
C7—C8—C9—C10	3.6 (5)	C9—C10—C23—C22	−2.5 (4)
C8—C9—C10—C23	−124.0 (3)	C11—C10—C23—C18	−4.8 (3)
C8—C9—C10—C11	58.1 (4)	C9—C10—C23—C18	177.2 (2)
C23—C10—C11—C12	−173.1 (2)	C21—C22—C23—C10	−178.5 (3)
C9—C10—C11—C12	4.8 (4)	C21—C22—C23—C18	1.8 (4)
C23—C10—C11—C16	5.7 (4)	C17—C18—C23—C10	0.8 (3)
C9—C10—C11—C16	−176.3 (2)	C19—C18—C23—C10	−179.3 (2)
C10—C11—C12—C13	−179.6 (3)	C17—C18—C23—C22	−179.5 (2)
C16—C11—C12—C13	1.5 (4)	C19—C18—C23—C22	0.4 (3)
C11—C12—C13—C14	1.2 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1ⁱ	0.93	2.47	3.290 (3)	147
C24—H24A···O1ⁱⁱ	0.96	2.59	3.176 (4)	120
C17—H17A···Cg1ⁱⁱⁱ	0.93	2.89	3.694 (3)	145

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

Experimental details

Crystal data
Chemical formula	C₂₄H₁₈O₂
M_r	338.38
Crystal system, space group	Monoclinic, Cc
Temperature (K)	293
a, b, c (Å)	5.5018 (2), 19.9215 (8), 16.0500 (7)
β (°)	95.072 (2)
V (Å³)	1752.26 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.54 × 0.27 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.958, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	7966, 1721, 1545
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.087, 1.07
No. of reflections	1721
No. of parameters	236
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.14

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
C8—H8A···O1ⁱ	0.93	2.47	3.290 (3)	147
C24—H24A···O1ⁱⁱ	0.96	2.59	3.176 (4)	120
C17—H17A···Cg1ⁱⁱⁱ	0.93	2.89	3.694 (3)	145

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

Footnotes

¹This paper is dedicated to the late His Royal Highness Prince Mahidol of Songkla for his contributions to the development of medical education in Thailand on the occasion of Mahidol Day which falls on the 24th September.

‡Thomson Reuters ResearcherID: A-5085-2009.

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

Acknowledgements

Financial support from the Thailand Research Fund (TRF) and Prince of Songkla University are gratefully acknowledged. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

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