1-(2-Naphth­yl)-3-phenyl­prop-2-en-1-one

Tang, S.-P.; Kuang, D.-Z.; Feng, Y.-L.; Chen, M.-S.; Li, W.

doi:10.1107/S1600536809025483

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1785

doi:10.1107/S1600536809025483

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1-(2-Naphthyl)-3-phenylprop-2-en-1-one

Si-Ping Tang,^a ^* Dai-Zhi Kuang,^a Yong-Lan Feng,^a Man-Sheng Chen ^a and Wei Li ^a

^aKey Laboratory of Functional Organometallic Materials, Hengyang Normal University, Hengyang, Hunan 421008, People's Republic of China
^*Correspondence e-mail: sptang88@163.com

(Received 20 June 2009; accepted 1 July 2009; online 4 July 2009)

The title compound, C₁₉H₁₄O, contains two independent molecules with the same s-cis conformation for the ketone unit. Both molecules are non-planar with dihedral angles of 51.9 (1) and 48.0 (1)° between the benzene ring and the naphthalene ring system. In the crystal, neighboring molecules are stabilized by intermolecular C—H⋯π interactions, giving a two-dimensional supramolecular array parallel to the ab plane.

Related literature

For background to chalcone and its derivatives, see: Agrinskaya et al. (1999 ); Indira et al. (2002 ); Opletalova (2000 ); Pandey et al. (2005 ). For related structures, see: Moorthi et al. (2005 ); Tang et al. (2008 ).

Experimental

Crystal data

C₁₉H₁₄O
M_r = 258.30
Triclinic, $[P \overline 1]$
a = 9.5878 (8) Å
b = 9.6111 (8) Å
c = 15.5358 (13) Å
α = 98.746 (2)°
β = 91.222 (2)°
γ = 105.764 (1)°
V = 1358.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.30 × 0.28 × 0.20 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.972, T_max = 0.982
10623 measured reflections
5271 independent reflections
3483 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.174
S = 1.03
5271 reflections
361 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3, Cg5 and Cg6 are the centroids of the C1–C10, C5–C10, C14–C19, C20–C29 and C24–C29 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1	0.93	2.49	2.814 (2)	101
C32—H32⋯O2	0.93	2.50	2.820 (2)	101
C18—H18⋯Cg1ⁱ	0.93	2.98	3.644	130
C15—H15⋯Cg2ⁱⁱ	0.93	2.94	3.642	134
C37—H37⋯Cg3ⁱⁱⁱ	0.93	2.96	3.610	128
C1—H1⋯Cg5ⁱⁱ	0.93	2.97	3.611	127
C6—H6⋯Cg6ⁱⁱⁱ	0.93	2.92	3.583	130
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1; (iii) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025483/at2828sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809025483/at2828Isup2.hkl

checkCIF report

Comment top

Chalcone and its analogues have been extensively researched because of their facile synthesis and potential applications as excellent non-linear optical materials (Agrinskaya et al., 1999; Indira et al., 2002) and biological activities (Opletalova, 2000; Pandey et al., 2005). Ongoing our efforts on the research of chalcone compounds (Tang et al., 2008), a new compound was here presented.

As shown in Fig.1, the title molecule contains two independent and isostructural molecules, which are non-planar because of the serious tilts between the benzene and naphthalene rings of 51.9 (1) ° and 48.0 (1) ° dihedral angles, respectively. In the two molecules, the ketone units display the same s-cis. conformations with the torsion angles of 14.7 (3) ° and 12.3 (3) °, respectively. Meanwhile, the intramolecular C—H···O hydrogen bonds exist within the ketone units, which are also found in the other similar structures (Moorthi et al., 2005; Tang et al., 2008).

In the crystal structure, as shown in Fig.2, neighboring molecules are stacked into a two-dimensional supramolecular layer by intermolecular C—H···π interactions parallel to the ab plane.

Related literature top

For background to chalcone and its derivatives, see: Agrinskaya et al. (1999); Indira et al. (2002); Opletalova (2000); Pandey et al. (2005). For related structures, see: Moorthi et al. (2005); Tang et al. (2008).

Experimental top

A mixture of 2-acetonaphthone (1.70 g, 10.0 mmol) and benzaldehyde (1.069 g, 10.0 mmol), sodium hydroxide (0.40 g, 10.0 mmol), ethanol (20 ml) and water (10 ml) was stirred at room temperature for 10 h. After filtering, the resulting precipitate was washed with water and iced ethanol, and further recrystallized from acetonitrile to afford colourless block crystals of the title compound [yield: 1.22 g (47.2 %)].

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The title molecule with displacement ellipsoids drawn at the 30% probability level, and H atoms as spheres of arbitrary radius.
	Fig. 2. Packing diagram of the title structure showing the C—H···O and C—H···π interactions. The H atoms not involved in hydrogen bonding have been omitted for clarity.

1-(2-Naphthyl)-3-phenylprop-2-en-1-one top

Crystal data top

C₁₉H₁₄O	Z = 4
M_r = 258.30	F(000) = 544
Triclinic, P1	D_x = 1.263 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5878 (8) Å	Cell parameters from 2584 reflections
b = 9.6111 (8) Å	θ = 2.2–26.9°
c = 15.5358 (13) Å	µ = 0.08 mm⁻¹
α = 98.746 (2)°	T = 295 K
β = 91.222 (2)°	Block, colourless
γ = 105.764 (1)°	0.30 × 0.28 × 0.20 mm
V = 1358.8 (2) Å³

Data collection top

Bruker SMART APEX area-detector diffractometer	5271 independent reflections
Radiation source: fine-focus sealed tube	3483 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.972, T_max = 0.982	k = −11→11
10623 measured reflections	l = −16→19

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.174	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0943P)² + 0.07P] where P = (F_o² + 2F_c²)/3
5271 reflections	(Δ/σ)_max < 0.001
361 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₉H₁₄O	γ = 105.764 (1)°
M_r = 258.30	V = 1358.8 (2) Å³
Triclinic, P1	Z = 4
a = 9.5878 (8) Å	Mo Kα radiation
b = 9.6111 (8) Å	µ = 0.08 mm⁻¹
c = 15.5358 (13) Å	T = 295 K
α = 98.746 (2)°	0.30 × 0.28 × 0.20 mm
β = 91.222 (2)°

Data collection top

Bruker SMART APEX area-detector diffractometer	5271 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3483 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.982	R_int = 0.017
10623 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.174	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
5271 reflections	Δρ_min = −0.19 e Å⁻³
361 parameters

Special details top

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 > 2sigma(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
C1	0.55561 (16)	0.34700 (16)	0.30964 (10)	0.0513 (4)
H1	0.6529	0.3967	0.3072	0.062*
C2	0.50388 (16)	0.31927 (16)	0.38862 (10)	0.0512 (4)
C3	0.35522 (17)	0.24451 (16)	0.39193 (11)	0.0564 (4)
H3	0.3193	0.2228	0.4449	0.068*
C4	0.26443 (17)	0.20422 (17)	0.31847 (11)	0.0569 (4)
H4	0.1666	0.1581	0.3224	0.068*
C5	0.31541 (16)	0.23088 (15)	0.23681 (10)	0.0492 (4)
C6	0.22432 (18)	0.18909 (17)	0.15896 (12)	0.0617 (4)
H6	0.1260	0.1428	0.1611	0.074*
C7	0.2783 (2)	0.2156 (2)	0.08125 (12)	0.0730 (5)
H7	0.2168	0.1879	0.0308	0.088*
C8	0.4258 (2)	0.2841 (2)	0.07654 (12)	0.0735 (5)
H8	0.4618	0.3014	0.0229	0.088*
C9	0.51710 (19)	0.32576 (18)	0.14943 (11)	0.0634 (5)
H9	0.6152	0.3705	0.1451	0.076*
C10	0.46492 (16)	0.30194 (15)	0.23190 (10)	0.0493 (4)
C11	0.60363 (17)	0.37413 (17)	0.46910 (11)	0.0556 (4)
C12	0.57387 (18)	0.29557 (18)	0.54382 (11)	0.0598 (4)
H12	0.5089	0.2024	0.5359	0.072*
C13	0.63803 (17)	0.35515 (17)	0.62227 (11)	0.0548 (4)
H13	0.6999	0.4496	0.6276	0.066*
C14	0.62209 (15)	0.28857 (16)	0.70127 (11)	0.0510 (4)
C15	0.67187 (17)	0.37583 (18)	0.78179 (11)	0.0581 (4)
H15	0.7170	0.4753	0.7845	0.070*
C16	0.65513 (19)	0.3166 (2)	0.85796 (12)	0.0693 (5)
H16	0.6880	0.3765	0.9114	0.083*
C17	0.59008 (19)	0.1694 (2)	0.85492 (13)	0.0728 (5)
H17	0.5791	0.1297	0.9062	0.087*
C18	0.54137 (18)	0.08120 (19)	0.77577 (13)	0.0678 (5)
H18	0.4979	−0.0184	0.7737	0.081*
C19	0.55654 (17)	0.13930 (17)	0.69964 (12)	0.0596 (4)
H19	0.5228	0.0785	0.6466	0.071*
C20	0.17274 (16)	0.87506 (16)	0.70822 (10)	0.0511 (4)
H20	0.2253	0.9728	0.7122	0.061*
C21	0.11862 (16)	0.79474 (16)	0.62779 (10)	0.0522 (4)
C22	0.03921 (17)	0.64537 (17)	0.62222 (11)	0.0590 (4)
H22	0.0000	0.5909	0.5682	0.071*
C23	0.01976 (17)	0.58105 (17)	0.69474 (11)	0.0592 (4)
H23	−0.0299	0.4822	0.6894	0.071*
C24	0.07335 (16)	0.66125 (16)	0.77786 (11)	0.0509 (4)
C25	0.05131 (18)	0.59894 (18)	0.85505 (12)	0.0639 (5)
H25	0.0025	0.5001	0.8513	0.077*
C26	0.10026 (19)	0.6810 (2)	0.93437 (12)	0.0701 (5)
H26	0.0844	0.6380	0.9843	0.084*
C27	0.17445 (19)	0.8298 (2)	0.94162 (12)	0.0675 (5)
H27	0.2066	0.8853	0.9964	0.081*
C28	0.19983 (17)	0.89384 (17)	0.86894 (11)	0.0584 (4)
H28	0.2505	0.9925	0.8745	0.070*
C29	0.15019 (15)	0.81224 (16)	0.78502 (10)	0.0489 (4)
C30	0.14645 (18)	0.86629 (18)	0.54882 (11)	0.0586 (4)
C31	0.04008 (18)	0.80888 (19)	0.47213 (11)	0.0641 (5)
H31	−0.0495	0.7444	0.4786	0.077*
C32	0.06982 (18)	0.84735 (17)	0.39480 (11)	0.0570 (4)
H32	0.1619	0.9090	0.3907	0.068*
C33	−0.02592 (17)	0.80371 (16)	0.31523 (10)	0.0519 (4)
C34	0.03151 (18)	0.83379 (17)	0.23635 (11)	0.0590 (4)
H34	0.1296	0.8816	0.2351	0.071*
C35	−0.0556 (2)	0.79344 (19)	0.16030 (12)	0.0668 (5)
H35	−0.0160	0.8138	0.1080	0.080*
C36	−0.2010 (2)	0.72311 (18)	0.16094 (12)	0.0664 (5)
H36	−0.2594	0.6956	0.1092	0.080*
C37	−0.25980 (18)	0.69361 (17)	0.23827 (12)	0.0628 (5)
H37	−0.3582	0.6465	0.2388	0.075*
C38	−0.17429 (17)	0.73317 (17)	0.31472 (11)	0.0581 (4)
H38	−0.2153	0.7129	0.3667	0.070*
O1	0.70779 (13)	0.48236 (13)	0.47157 (8)	0.0757 (4)
O2	0.25405 (14)	0.96832 (14)	0.54733 (8)	0.0820 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0439 (8)	0.0479 (8)	0.0599 (10)	0.0099 (6)	0.0067 (7)	0.0072 (7)
C2	0.0504 (9)	0.0477 (8)	0.0545 (9)	0.0131 (7)	0.0059 (7)	0.0058 (7)
C3	0.0554 (9)	0.0568 (9)	0.0559 (10)	0.0126 (7)	0.0119 (8)	0.0105 (7)
C4	0.0468 (9)	0.0538 (9)	0.0677 (11)	0.0100 (7)	0.0082 (8)	0.0096 (8)
C5	0.0478 (8)	0.0433 (8)	0.0577 (10)	0.0160 (6)	0.0038 (7)	0.0060 (7)
C6	0.0529 (9)	0.0570 (9)	0.0723 (12)	0.0134 (7)	−0.0040 (8)	0.0059 (8)
C7	0.0762 (13)	0.0800 (12)	0.0596 (11)	0.0207 (10)	−0.0071 (9)	0.0047 (9)
C8	0.0792 (13)	0.0863 (13)	0.0551 (11)	0.0230 (10)	0.0082 (9)	0.0115 (9)
C9	0.0600 (10)	0.0676 (10)	0.0620 (11)	0.0160 (8)	0.0134 (8)	0.0114 (8)
C10	0.0498 (9)	0.0432 (8)	0.0561 (9)	0.0150 (6)	0.0063 (7)	0.0071 (7)
C11	0.0532 (9)	0.0548 (9)	0.0561 (10)	0.0129 (7)	0.0074 (7)	0.0042 (7)
C12	0.0585 (10)	0.0542 (9)	0.0621 (11)	0.0101 (7)	−0.0001 (8)	0.0062 (8)
C13	0.0482 (9)	0.0516 (9)	0.0629 (10)	0.0111 (7)	0.0015 (7)	0.0095 (7)
C14	0.0414 (8)	0.0522 (9)	0.0596 (10)	0.0134 (7)	0.0013 (7)	0.0090 (7)
C15	0.0518 (9)	0.0571 (9)	0.0629 (11)	0.0118 (7)	−0.0012 (8)	0.0091 (8)
C16	0.0642 (11)	0.0820 (13)	0.0599 (11)	0.0181 (9)	−0.0020 (8)	0.0110 (9)
C17	0.0624 (11)	0.0871 (13)	0.0783 (13)	0.0238 (10)	0.0067 (10)	0.0364 (11)
C18	0.0545 (10)	0.0579 (10)	0.0948 (14)	0.0149 (8)	0.0027 (9)	0.0262 (10)
C19	0.0514 (9)	0.0541 (9)	0.0727 (11)	0.0144 (7)	−0.0026 (8)	0.0101 (8)
C20	0.0449 (8)	0.0442 (8)	0.0612 (10)	0.0084 (6)	0.0009 (7)	0.0064 (7)
C21	0.0451 (8)	0.0546 (9)	0.0555 (10)	0.0136 (7)	0.0012 (7)	0.0053 (7)
C22	0.0555 (9)	0.0529 (9)	0.0624 (10)	0.0122 (7)	−0.0045 (8)	−0.0034 (8)
C23	0.0537 (9)	0.0454 (8)	0.0747 (12)	0.0110 (7)	−0.0006 (8)	0.0045 (8)
C24	0.0418 (8)	0.0465 (8)	0.0653 (10)	0.0139 (6)	0.0016 (7)	0.0095 (7)
C25	0.0592 (10)	0.0544 (9)	0.0807 (12)	0.0146 (8)	0.0026 (9)	0.0219 (9)
C26	0.0708 (12)	0.0732 (12)	0.0702 (12)	0.0192 (9)	0.0039 (9)	0.0255 (10)
C27	0.0689 (11)	0.0751 (12)	0.0568 (10)	0.0190 (9)	−0.0034 (8)	0.0085 (9)
C28	0.0585 (10)	0.0523 (9)	0.0604 (10)	0.0119 (7)	−0.0016 (8)	0.0050 (8)
C29	0.0418 (8)	0.0480 (8)	0.0563 (10)	0.0128 (6)	0.0008 (7)	0.0063 (7)
C30	0.0520 (9)	0.0614 (10)	0.0574 (10)	0.0104 (8)	0.0046 (7)	0.0045 (8)
C31	0.0550 (10)	0.0697 (11)	0.0607 (11)	0.0064 (8)	0.0034 (8)	0.0100 (8)
C32	0.0531 (9)	0.0526 (9)	0.0617 (11)	0.0094 (7)	0.0045 (8)	0.0084 (8)
C33	0.0511 (9)	0.0452 (8)	0.0593 (10)	0.0124 (7)	0.0021 (7)	0.0105 (7)
C34	0.0554 (9)	0.0561 (9)	0.0659 (11)	0.0124 (7)	0.0100 (8)	0.0159 (8)
C35	0.0761 (12)	0.0660 (11)	0.0601 (11)	0.0196 (9)	0.0090 (9)	0.0154 (8)
C36	0.0708 (12)	0.0614 (10)	0.0661 (11)	0.0182 (9)	−0.0082 (9)	0.0097 (8)
C37	0.0507 (9)	0.0572 (10)	0.0794 (12)	0.0122 (7)	−0.0023 (9)	0.0145 (9)
C38	0.0541 (9)	0.0588 (10)	0.0621 (10)	0.0131 (7)	0.0070 (8)	0.0168 (8)
O1	0.0676 (8)	0.0766 (8)	0.0653 (8)	−0.0072 (6)	0.0031 (6)	0.0079 (6)
O2	0.0733 (8)	0.0853 (9)	0.0667 (8)	−0.0125 (7)	−0.0006 (6)	0.0129 (6)

Geometric parameters (Å, º) top

C1—C2	1.370 (2)	C20—C21	1.374 (2)
C1—C10	1.412 (2)	C20—C29	1.412 (2)
C1—H1	0.9300	C20—H20	0.9300
C2—C3	1.417 (2)	C21—C22	1.419 (2)
C2—C11	1.493 (2)	C21—C30	1.490 (2)
C3—C4	1.360 (2)	C22—C23	1.358 (2)
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.404 (2)	C23—C24	1.407 (2)
C4—H4	0.9300	C23—H23	0.9300
C5—C6	1.415 (2)	C24—C25	1.415 (2)
C5—C10	1.420 (2)	C24—C29	1.424 (2)
C6—C7	1.356 (2)	C25—C26	1.356 (2)
C6—H6	0.9300	C25—H25	0.9300
C7—C8	1.397 (3)	C26—C27	1.400 (2)
C7—H7	0.9300	C26—H26	0.9300
C8—C9	1.356 (2)	C27—C28	1.362 (2)
C8—H8	0.9300	C27—H27	0.9300
C9—C10	1.414 (2)	C28—C29	1.415 (2)
C9—H9	0.9300	C28—H28	0.9300
C11—O1	1.2258 (18)	C30—O2	1.2184 (18)
C11—C12	1.471 (2)	C30—C31	1.485 (2)
C12—C13	1.325 (2)	C31—C32	1.324 (2)
C12—H12	0.9300	C31—H31	0.9300
C13—C14	1.460 (2)	C32—C33	1.460 (2)
C13—H13	0.9300	C32—H32	0.9300
C14—C15	1.391 (2)	C33—C34	1.392 (2)
C14—C19	1.397 (2)	C33—C38	1.399 (2)
C15—C16	1.383 (2)	C34—C35	1.374 (2)
C15—H15	0.9300	C34—H34	0.9300
C16—C17	1.375 (3)	C35—C36	1.375 (2)
C16—H16	0.9300	C35—H35	0.9300
C17—C18	1.376 (3)	C36—C37	1.374 (2)
C17—H17	0.9300	C36—H36	0.9300
C18—C19	1.377 (2)	C37—C38	1.371 (2)
C18—H18	0.9300	C37—H37	0.9300
C19—H19	0.9300	C38—H38	0.9300

C2—C1—C10	121.64 (14)	C21—C20—C29	121.38 (14)
C2—C1—H1	119.2	C21—C20—H20	119.3
C10—C1—H1	119.2	C29—C20—H20	119.3
C1—C2—C3	118.81 (14)	C20—C21—C22	119.00 (15)
C1—C2—C11	119.27 (14)	C20—C21—C30	119.14 (14)
C3—C2—C11	121.86 (14)	C22—C21—C30	121.86 (14)
C4—C3—C2	120.73 (15)	C23—C22—C21	120.81 (15)
C4—C3—H3	119.6	C23—C22—H22	119.6
C2—C3—H3	119.6	C21—C22—H22	119.6
C3—C4—C5	121.34 (15)	C22—C23—C24	121.21 (14)
C3—C4—H4	119.3	C22—C23—H23	119.4
C5—C4—H4	119.3	C24—C23—H23	119.4
C4—C5—C6	122.83 (15)	C23—C24—C25	122.72 (14)
C4—C5—C10	118.66 (14)	C23—C24—C29	118.78 (15)
C6—C5—C10	118.50 (15)	C25—C24—C29	118.49 (15)
C7—C6—C5	120.92 (16)	C26—C25—C24	121.06 (15)
C7—C6—H6	119.5	C26—C25—H25	119.5
C5—C6—H6	119.5	C24—C25—H25	119.5
C6—C7—C8	120.41 (17)	C25—C26—C27	120.53 (17)
C6—C7—H7	119.8	C25—C26—H26	119.7
C8—C7—H7	119.8	C27—C26—H26	119.7
C9—C8—C7	120.66 (17)	C28—C27—C26	120.38 (16)
C9—C8—H8	119.7	C28—C27—H27	119.8
C7—C8—H8	119.7	C26—C27—H27	119.8
C8—C9—C10	120.75 (16)	C27—C28—C29	120.85 (15)
C8—C9—H9	119.6	C27—C28—H28	119.6
C10—C9—H9	119.6	C29—C28—H28	119.6
C1—C10—C9	122.51 (14)	C20—C29—C28	122.54 (14)
C1—C10—C5	118.75 (14)	C20—C29—C24	118.78 (14)
C9—C10—C5	118.74 (15)	C28—C29—C24	118.68 (15)
O1—C11—C12	121.57 (15)	O2—C30—C31	121.21 (16)
O1—C11—C2	119.81 (15)	O2—C30—C21	120.69 (15)
C12—C11—C2	118.62 (13)	C31—C30—C21	118.09 (14)
C13—C12—C11	121.17 (15)	C32—C31—C30	121.54 (15)
C13—C12—H12	119.4	C32—C31—H31	119.2
C11—C12—H12	119.4	C30—C31—H31	119.2
C12—C13—C14	127.04 (15)	C31—C32—C33	127.23 (15)
C12—C13—H13	116.5	C31—C32—H32	116.4
C14—C13—H13	116.5	C33—C32—H32	116.4
C15—C14—C19	118.01 (16)	C34—C33—C38	118.17 (15)
C15—C14—C13	119.50 (14)	C34—C33—C32	119.13 (14)
C19—C14—C13	122.48 (15)	C38—C33—C32	122.70 (15)
C16—C15—C14	120.84 (16)	C35—C34—C33	120.51 (16)
C16—C15—H15	119.6	C35—C34—H34	119.7
C14—C15—H15	119.6	C33—C34—H34	119.7
C17—C16—C15	120.22 (17)	C34—C35—C36	120.51 (17)
C17—C16—H16	119.9	C34—C35—H35	119.7
C15—C16—H16	119.9	C36—C35—H35	119.7
C16—C17—C18	119.73 (18)	C37—C36—C35	119.78 (17)
C16—C17—H17	120.1	C37—C36—H36	120.1
C18—C17—H17	120.1	C35—C36—H36	120.1
C17—C18—C19	120.50 (16)	C38—C37—C36	120.42 (16)
C17—C18—H18	119.8	C38—C37—H37	119.8
C19—C18—H18	119.8	C36—C37—H37	119.8
C18—C19—C14	120.70 (16)	C37—C38—C33	120.61 (16)
C18—C19—H19	119.7	C37—C38—H38	119.7
C14—C19—H19	119.7	C33—C38—H38	119.7

C10—C1—C2—C3	−0.5 (2)	C29—C20—C21—C22	−0.4 (2)
C10—C1—C2—C11	−177.88 (13)	C29—C20—C21—C30	−179.62 (13)
C1—C2—C3—C4	−1.7 (2)	C20—C21—C22—C23	−1.7 (2)
C11—C2—C3—C4	175.60 (14)	C30—C21—C22—C23	177.56 (14)
C2—C3—C4—C5	2.1 (2)	C21—C22—C23—C24	2.1 (3)
C3—C4—C5—C6	179.33 (14)	C22—C23—C24—C25	178.04 (15)
C3—C4—C5—C10	−0.3 (2)	C22—C23—C24—C29	−0.5 (2)
C4—C5—C6—C7	−179.29 (15)	C23—C24—C25—C26	−177.69 (15)
C10—C5—C6—C7	0.3 (2)	C29—C24—C25—C26	0.9 (2)
C5—C6—C7—C8	0.4 (3)	C24—C25—C26—C27	−0.2 (3)
C6—C7—C8—C9	−0.3 (3)	C25—C26—C27—C28	−0.7 (3)
C7—C8—C9—C10	−0.6 (3)	C26—C27—C28—C29	0.9 (3)
C2—C1—C10—C9	−178.13 (14)	C21—C20—C29—C28	−177.50 (14)
C2—C1—C10—C5	2.3 (2)	C21—C20—C29—C24	1.9 (2)
C8—C9—C10—C1	−178.34 (15)	C27—C28—C29—C20	179.19 (14)
C8—C9—C10—C5	1.2 (2)	C27—C28—C29—C24	−0.2 (2)
C4—C5—C10—C1	−1.9 (2)	C23—C24—C29—C20	−1.5 (2)
C6—C5—C10—C1	178.51 (13)	C25—C24—C29—C20	179.91 (13)
C4—C5—C10—C9	178.52 (14)	C23—C24—C29—C28	177.96 (14)
C6—C5—C10—C9	−1.1 (2)	C25—C24—C29—C28	−0.7 (2)
C1—C2—C11—O1	26.3 (2)	C20—C21—C30—O2	27.6 (2)
C3—C2—C11—O1	−150.94 (16)	C22—C21—C30—O2	−151.59 (17)
C1—C2—C11—C12	−153.52 (15)	C20—C21—C30—C31	−152.83 (15)
C3—C2—C11—C12	29.2 (2)	C22—C21—C30—C31	27.9 (2)
O1—C11—C12—C13	14.7 (3)	O2—C30—C31—C32	12.3 (3)
C2—C11—C12—C13	−165.43 (15)	C21—C30—C31—C32	−167.26 (15)
C11—C12—C13—C14	−178.11 (14)	C30—C31—C32—C33	−177.63 (15)
C12—C13—C14—C15	−166.36 (16)	C31—C32—C33—C34	−168.95 (16)
C12—C13—C14—C19	12.8 (3)	C31—C32—C33—C38	11.4 (3)
C19—C14—C15—C16	−0.8 (2)	C38—C33—C34—C35	−0.7 (2)
C13—C14—C15—C16	178.42 (14)	C32—C33—C34—C35	179.67 (15)
C14—C15—C16—C17	0.7 (3)	C33—C34—C35—C36	0.2 (3)
C15—C16—C17—C18	−0.1 (3)	C34—C35—C36—C37	0.3 (3)
C16—C17—C18—C19	−0.4 (3)	C35—C36—C37—C38	−0.3 (3)
C17—C18—C19—C14	0.3 (3)	C36—C37—C38—C33	−0.2 (3)
C15—C14—C19—C18	0.3 (2)	C34—C33—C38—C37	0.7 (2)
C13—C14—C19—C18	−178.88 (14)	C32—C33—C38—C37	−179.68 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.93	2.49	2.814 (2)	101
C32—H32···O2	0.93	2.50	2.820 (2)	101
C18—H18···Cg1ⁱ	0.93	2.98	3.644	130
C15—H15···Cg2ⁱⁱ	0.93	2.94	3.642	134
C37—H37···Cg3ⁱⁱⁱ	0.93	2.96	3.610	128
C1—H1···Cg5ⁱⁱ	0.93	2.97	3.611	127
C6—H6···Cg6ⁱⁱⁱ	0.93	2.92	3.583	130

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₄O
M_r	258.30
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	9.5878 (8), 9.6111 (8), 15.5358 (13)
α, β, γ (°)	98.746 (2), 91.222 (2), 105.764 (1)
V (Å³)	1358.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.28 × 0.20

Data collection
Diffractometer	Bruker SMART APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.972, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	10623, 5271, 3483
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.174, 1.03
No. of reflections	5271
No. of parameters	361
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.19

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.93	2.49	2.814 (2)	100.5
C32—H32···O2	0.93	2.50	2.820 (2)	100.6
C18—H18···Cg1ⁱ	0.93	2.98	3.644	130
C15—H15···Cg2ⁱⁱ	0.93	2.94	3.642	134
C37—H37···Cg3ⁱⁱⁱ	0.93	2.96	3.610	128
C1—H1···Cg5ⁱⁱ	0.93	2.97	3.611	127
C6—H6···Cg6ⁱⁱⁱ	0.93	2.92	3.583	130

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

Acknowledgements

We thank the Construct Program for Key Disciplines in Hunan Province and the Foundation of Hunan Province Education Office (No. 08 C178) for supporting this study.

References

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