(E)-1-(4-Amino­phen­yl)-3-(naphthalen-2-yl)prop-2-en-1-one

Kobkeatthawin, T.; Chantrapromma, S.; Saewan, N.; Fun, H.-K.

doi:10.1107/S1600536811014024

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages o1204-o1205

doi:10.1107/S1600536811014024

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(E)-1-(4-Aminophenyl)-3-(naphthalen-2-yl)prop-2-en-1-one

Thawanrat Kobkeatthawin,^a Suchada Chantrapromma,^a ^*‡ Nisakorn Saewan ^b and Hoong-Kun Fun ^c §

^aCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^bSchool of Cosmetic Science, Mae Fah Luang University, Muang, Chiang Rai 57100, Thailand, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: suchada.c@psu.ac.th

(Received 29 March 2011; accepted 13 April 2011; online 22 April 2011)

The molecule of the title chalcone derivative, C₁₉H₁₅NO, exists in a trans configuration with respect to the C=C double bond. The molecule is slightly twisted with a dihedral angle of 6.12 (12)° between the benzene ring and the naphthalene ring system. The prop-2-en-1-one bridge is nearly planar, with an r.m.s. deviation of 0.0194 (2), and makes dihedral angles of 8.05 (19) and 11.47 (18)° with the benzene ring and the naphthalene ring system, respectively. In the crystal, molecules are linked by N—H⋯O hydrogen bonds into chains along the b axis. Weak N—H⋯π and C—H⋯π interactions and a short N⋯O contact [2.974 (4) Å] are also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ). For related structures, see: Fun et al. (2008 ); Horkaew et al. (2010 ). For background to and applications of chalcones, see: Bandgar & Gawande (2010 ); Cheng et al. (2008); Gaber et al. (2008 ); Nerya et al. (2004 ); Nowakowska et al. (2008 ); Patil et al. (2007 ); Svetlichny et al. (2007 ); Tewtrakul et al. (2003 ); Xu et al. (2005 ). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ).

Experimental

Crystal data

C₁₉H₁₅NO
M_r = 273.32
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.7422 (6) Å
b = 9.8022 (10) Å
c = 25.504 (3) Å
V = 1435.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.32 × 0.28 × 0.07 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.976, T_max = 0.994
8109 measured reflections
1940 independent reflections
1633 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.119
S = 1.14
1940 reflections
198 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C10–C12/C17–C19 and C12–C17 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1ⁱ	0.90 (4)	2.12 (4)	2.974 (4)	159 (4)
N1—H2N1⋯Cg1ⁱⁱ	0.86 (4)	2.99 (4)	3.475 (3)	118 (3)
C5—H5A⋯Cg3ⁱⁱⁱ	0.93	2.82	3.513 (3)	132
C11—H11A⋯Cg3^iv	0.93	2.92	3.631 (3)	135
C13—H13A⋯Cg2^iv	0.93	2.86	3.551 (3)	132
C16—H16A⋯Cg1ⁱⁱⁱ	0.93	2.87	3.603 (4)	136
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iii) $[-x-1, y+{\script{3\over 2}}, -z+{\script{5\over 2}}]$ ; (iv) $[-x, y+{\script{1\over 2}}, -z+{\script{5\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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/S1600536811014024/rz2579sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811014024/rz2579Isup2.hkl

checkCIF report

Comment top

Chalcones are the precursors of flavonoids and antiflavonoids which are available in plenty in ferns and higher plants. Their derivatives are known to display a variety of biological properties such as analgesic, anti-inflammatory, antibacterial and antifungal activities (Bandgar & Gawande, 2010; Cheng et al., 2008; Nowakowska et al., 2008), HIV-1 protease inhibitory (Tewtrakul et al., 2003) and tyrosinase inhibitory (Nerya et al., 2004) activities. Moreover, some of them have also been studied for fluorescent property (Gaber et al., 2008) and used for sensor, liquid crystal display and fluorescence probe for sensing of DNA or proteins (Svetlichny et al., 2007; Xu et al., 2005). In addition, some of them exhibit second harmonic generation (SHG), and hence are used in non-linear optical (NLO) applications (Patil et al., 2007). These interesting properties of chalcones have lead us to synthesize the title compound, (I), which contains the amino and fluorophore (naphthalene) groups in order to study its NLO and fluorescent properties. Compound (I) crystallizes in the chiral orthorhombic P2₁2₁2₁ space group and should therefore exhibit second-order nonlinear optical properties. (I) also shows fluorescent emission at 440 nm when excited at 380 nm. Our results also showed that (I) was inactive for tyrosinase inhibitory. Herein the crystal structure of (I) is reported.

The molecule of the title chalcone derivative (Fig. 1), C₁₉H₁₅NO, exists in an E configuration with respect to the C8═C9 ethenyl bond [1.330 (4) Å], as indicated by the torsion angle C7–C8–C9–C10 = 179.1 (3)°. The molecule is slightly twisted with the dihedral angle between the benzene and naphthalene rings of 6.12 (12)°. The prop-2-en-1-one unit (C7—C9/O1) is nearly planar [r.m.s. of 0.0194 (2) Å] and the torsion angle O1–C7–C8–C9 is 6.4 (5)°. This middle bridge makes dihedral angles of 8.05 (19) and 11.47 (18) ° with the benzene and naphthalene rings, respectively. The bond distances are of normal values (Allen et al., 1987) and are comparable with those found in related structures (Fun et al., 2008; Horkaew et al., 2010).

In the crystal packing, the molecules are linked by N—H···O hydrogen bonds (Table 1) into chains along the b axis (Fig. 2). N—H···π and C—H···π weak interactions (Table 1) are present in the crystal. In addition, a N···O short contact [2.974 (4) Å; symmetry code 2 - x, 1/2 + y, 3/2 - z] is also observed.

Related literature top

For bond-length data, see: Allen et al. (1987). For related structures, see: Fun et al. (2008); Horkaew et al. (2010). For background to and applications of chalcones, see: Bandgar & Gawande (2010); Cheng et al. (2008); Gaber et al. (2008); Nerya et al. (2004); Nowakowska et al. (2008); Patil et al. (2007); Svetlichny et al. (2007); Tewtrakul et al. (2003); Xu et al. (2005). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986).

Experimental top

The title compound was synthesized by condensation of 4-aminoacetophenone (0.40 g, 3 mmol) with 2-naphthaldehyde (0.46 g, 3 mmol) in ethanol (25 ml) in the presence of 20% NaOH(aq) (5 ml). After stirring for 6 h at room temperature, the resulting yellow solid was collected by filtration, washed with distilled diethylether, dried and purified by repeated recrysallization from acetone. Yellow plate-shaped single crystals of the title compound suitable for X-ray structure determination were recrystalized from acetone by slow evaporation of the solvent at room temperature after several days. M.p. 416–417 K.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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.
	Fig. 2. The crystal packing of the title compound viewed along the a axis, showing chains running along the [010] direction.

(E)-1-(4-Aminophenyl)-3-(naphthalen-2-yl)prop-2-en-1-one top

Crystal data top

C₁₉H₁₅NO	D_x = 1.265 Mg m⁻³
M_r = 273.32	Melting point = 416–417 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1940 reflections
a = 5.7422 (6) Å	θ = 2.2–27.5°
b = 9.8022 (10) Å	µ = 0.08 mm⁻¹
c = 25.504 (3) Å	T = 100 K
V = 1435.5 (3) Å³	Plate, yellow
Z = 4	0.32 × 0.28 × 0.07 mm
F(000) = 576

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	1940 independent reflections
Radiation source: sealed tube	1633 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→7
T_min = 0.976, T_max = 0.994	k = −9→12
8109 measured reflections	l = −32→33

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ²(F_o²) + (0.0233P)² + 1.3561P] where P = (F_o² + 2F_c²)/3
1940 reflections	(Δ/σ)_max = 0.001
198 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₉H₁₅NO	V = 1435.5 (3) Å³
M_r = 273.32	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.7422 (6) Å	µ = 0.08 mm⁻¹
b = 9.8022 (10) Å	T = 100 K
c = 25.504 (3) Å	0.32 × 0.28 × 0.07 mm

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	1940 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1633 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.994	R_int = 0.042
8109 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	Δρ_max = 0.29 e Å⁻³
1940 reflections	Δρ_min = −0.24 e Å⁻³
198 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 100.0 (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
O1	1.1598 (4)	0.7032 (2)	0.85128 (9)	0.0266 (5)
N1	0.5373 (7)	1.1585 (3)	0.74175 (13)	0.0339 (8)
H2N1	0.409 (8)	1.195 (4)	0.7515 (15)	0.045 (13)*
H1N1	0.599 (7)	1.187 (4)	0.7112 (14)	0.033 (11)*
C1	0.8419 (6)	0.8481 (3)	0.83133 (11)	0.0201 (7)
C2	0.9516 (6)	0.9000 (3)	0.78648 (12)	0.0224 (7)
H2A	1.0945	0.8641	0.7763	0.027*
C3	0.8535 (6)	1.0026 (3)	0.75714 (12)	0.0230 (7)
H3A	0.9314	1.0356	0.7278	0.028*
C4	0.6354 (6)	1.0583 (3)	0.77112 (12)	0.0233 (7)
C5	0.5252 (6)	1.0072 (3)	0.81610 (12)	0.0232 (7)
H5A	0.3827	1.0434	0.8264	0.028*
C6	0.6244 (6)	0.9045 (3)	0.84519 (12)	0.0219 (7)
H6A	0.5466	0.8715	0.8746	0.026*
C7	0.9597 (6)	0.7405 (3)	0.86224 (13)	0.0222 (7)
C8	0.8373 (6)	0.6782 (3)	0.90735 (12)	0.0221 (7)
H8A	0.6818	0.7000	0.9133	0.027*
C9	0.9441 (6)	0.5920 (3)	0.93962 (11)	0.0198 (7)
H9A	1.0988	0.5718	0.9321	0.024*
C10	0.8433 (6)	0.5257 (3)	0.98562 (12)	0.0187 (7)
C11	0.9577 (6)	0.4164 (3)	1.00866 (11)	0.0204 (7)
H11A	1.1021	0.3900	0.9956	0.025*
C12	0.8612 (6)	0.3438 (3)	1.05134 (12)	0.0199 (7)
C13	0.9733 (6)	0.2294 (3)	1.07446 (12)	0.0234 (7)
H13A	1.1171	0.2010	1.0617	0.028*
C14	0.8731 (7)	0.1609 (3)	1.11511 (13)	0.0275 (8)
H14A	0.9490	0.0864	1.1299	0.033*
C15	0.6544 (7)	0.2022 (3)	1.13492 (13)	0.0276 (8)
H15A	0.5864	0.1540	1.1624	0.033*
C16	0.5423 (7)	0.3123 (3)	1.11405 (12)	0.0263 (7)
H16A	0.3998	0.3395	1.1279	0.032*
C17	0.6402 (6)	0.3855 (3)	1.07164 (11)	0.0196 (7)
C18	0.5282 (6)	0.4987 (3)	1.04803 (12)	0.0220 (7)
H18A	0.3853	0.5277	1.0611	0.026*
C19	0.6240 (6)	0.5658 (3)	1.00685 (12)	0.0211 (7)
H19A	0.5453	0.6395	0.9922	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0249 (13)	0.0254 (11)	0.0297 (12)	0.0044 (12)	0.0068 (11)	0.0020 (10)
N1	0.0305 (19)	0.0385 (18)	0.0326 (17)	0.0104 (17)	0.0064 (16)	0.0122 (15)
C1	0.0240 (18)	0.0180 (15)	0.0185 (14)	−0.0039 (15)	−0.0014 (14)	−0.0037 (12)
C2	0.0215 (17)	0.0213 (15)	0.0244 (16)	−0.0025 (15)	0.0041 (14)	−0.0062 (13)
C3	0.0257 (18)	0.0216 (15)	0.0216 (15)	−0.0037 (17)	0.0047 (15)	−0.0005 (13)
C4	0.0236 (17)	0.0226 (15)	0.0237 (15)	−0.0024 (16)	−0.0032 (15)	−0.0039 (13)
C5	0.0183 (17)	0.0272 (16)	0.0242 (15)	0.0003 (15)	0.0017 (14)	−0.0039 (14)
C6	0.0196 (17)	0.0233 (15)	0.0229 (15)	−0.0050 (15)	0.0028 (14)	−0.0033 (13)
C7	0.0227 (17)	0.0184 (15)	0.0256 (16)	−0.0021 (15)	0.0001 (15)	−0.0051 (13)
C8	0.0242 (18)	0.0152 (14)	0.0269 (15)	−0.0016 (15)	0.0052 (15)	−0.0045 (13)
C9	0.0203 (16)	0.0113 (13)	0.0278 (16)	−0.0040 (13)	0.0037 (14)	−0.0071 (12)
C10	0.0207 (16)	0.0121 (14)	0.0234 (15)	−0.0012 (13)	−0.0001 (14)	−0.0065 (11)
C11	0.0153 (15)	0.0220 (15)	0.0240 (15)	−0.0012 (15)	0.0005 (14)	−0.0075 (13)
C12	0.0202 (17)	0.0171 (14)	0.0225 (14)	−0.0037 (15)	−0.0026 (14)	−0.0074 (12)
C13	0.0234 (17)	0.0188 (15)	0.0281 (16)	−0.0019 (15)	−0.0033 (15)	−0.0065 (13)
C14	0.035 (2)	0.0181 (15)	0.0297 (17)	0.0039 (16)	−0.0075 (17)	−0.0003 (14)
C15	0.035 (2)	0.0226 (16)	0.0255 (16)	−0.0092 (17)	0.0008 (17)	0.0016 (13)
C16	0.0245 (18)	0.0296 (17)	0.0249 (16)	−0.0078 (17)	0.0015 (15)	−0.0075 (14)
C17	0.0198 (16)	0.0196 (14)	0.0196 (14)	−0.0024 (14)	0.0009 (14)	−0.0085 (12)
C18	0.0188 (16)	0.0220 (15)	0.0251 (15)	0.0022 (15)	0.0027 (14)	−0.0069 (13)
C19	0.0221 (17)	0.0152 (14)	0.0261 (15)	0.0084 (15)	−0.0014 (14)	−0.0020 (13)

Geometric parameters (Å, º) top

O1—C7	1.238 (4)	C9—H9A	0.9300
N1—C4	1.358 (4)	C10—C11	1.388 (4)
N1—H2N1	0.86 (4)	C10—C19	1.426 (5)
N1—H1N1	0.90 (4)	C11—C12	1.413 (4)
C1—C2	1.402 (4)	C11—H11A	0.9300
C1—C6	1.411 (5)	C12—C13	1.421 (4)
C1—C7	1.480 (4)	C12—C17	1.430 (5)
C2—C3	1.374 (4)	C13—C14	1.363 (5)
C2—H2A	0.9300	C13—H13A	0.9300
C3—C4	1.412 (5)	C14—C15	1.413 (5)
C3—H3A	0.9300	C14—H14A	0.9300
C4—C5	1.403 (4)	C15—C16	1.364 (5)
C5—C6	1.374 (4)	C15—H15A	0.9300
C5—H5A	0.9300	C16—C17	1.415 (4)
C6—H6A	0.9300	C16—H16A	0.9300
C7—C8	1.480 (4)	C17—C18	1.417 (4)
C8—C9	1.330 (4)	C18—C19	1.356 (4)
C8—H8A	0.9300	C18—H18A	0.9300
C9—C10	1.461 (4)	C19—H19A	0.9300

C4—N1—H2N1	120 (3)	C11—C10—C19	118.1 (3)
C4—N1—H1N1	123 (2)	C11—C10—C9	119.7 (3)
H2N1—N1—H1N1	117 (4)	C19—C10—C9	122.1 (3)
C2—C1—C6	117.4 (3)	C10—C11—C12	121.9 (3)
C2—C1—C7	119.2 (3)	C10—C11—H11A	119.0
C6—C1—C7	123.4 (3)	C12—C11—H11A	119.0
C3—C2—C1	121.7 (3)	C11—C12—C13	122.6 (3)
C3—C2—H2A	119.1	C11—C12—C17	118.9 (3)
C1—C2—H2A	119.1	C13—C12—C17	118.5 (3)
C2—C3—C4	120.6 (3)	C14—C13—C12	120.9 (3)
C2—C3—H3A	119.7	C14—C13—H13A	119.6
C4—C3—H3A	119.7	C12—C13—H13A	119.6
N1—C4—C5	121.5 (3)	C13—C14—C15	120.4 (3)
N1—C4—C3	120.6 (3)	C13—C14—H14A	119.8
C5—C4—C3	117.9 (3)	C15—C14—H14A	119.8
C6—C5—C4	121.1 (3)	C16—C15—C14	120.4 (3)
C6—C5—H5A	119.4	C16—C15—H15A	119.8
C4—C5—H5A	119.4	C14—C15—H15A	119.8
C5—C6—C1	121.2 (3)	C15—C16—C17	120.8 (3)
C5—C6—H6A	119.4	C15—C16—H16A	119.6
C1—C6—H6A	119.4	C17—C16—H16A	119.6
O1—C7—C8	119.6 (3)	C16—C17—C18	122.8 (3)
O1—C7—C1	121.0 (3)	C16—C17—C12	118.9 (3)
C8—C7—C1	119.4 (3)	C18—C17—C12	118.2 (3)
C9—C8—C7	121.6 (3)	C19—C18—C17	121.7 (3)
C9—C8—H8A	119.2	C19—C18—H18A	119.2
C7—C8—H8A	119.2	C17—C18—H18A	119.2
C8—C9—C10	126.7 (3)	C18—C19—C10	121.2 (3)
C8—C9—H9A	116.7	C18—C19—H19A	119.4
C10—C9—H9A	116.7	C10—C19—H19A	119.4

C6—C1—C2—C3	0.5 (4)	C9—C10—C11—C12	−176.3 (3)
C7—C1—C2—C3	−178.1 (3)	C10—C11—C12—C13	178.3 (3)
C1—C2—C3—C4	−0.7 (5)	C10—C11—C12—C17	−0.7 (4)
C2—C3—C4—N1	−179.2 (3)	C11—C12—C13—C14	−179.0 (3)
C2—C3—C4—C5	1.0 (5)	C17—C12—C13—C14	0.0 (4)
N1—C4—C5—C6	179.1 (3)	C12—C13—C14—C15	0.2 (5)
C3—C4—C5—C6	−1.0 (5)	C13—C14—C15—C16	−0.8 (5)
C4—C5—C6—C1	0.9 (5)	C14—C15—C16—C17	1.2 (5)
C2—C1—C6—C5	−0.6 (4)	C15—C16—C17—C18	178.7 (3)
C7—C1—C6—C5	178.0 (3)	C15—C16—C17—C12	−1.0 (5)
C2—C1—C7—O1	5.3 (4)	C11—C12—C17—C16	179.4 (3)
C6—C1—C7—O1	−173.3 (3)	C13—C12—C17—C16	0.4 (4)
C2—C1—C7—C8	−175.6 (3)	C11—C12—C17—C18	−0.3 (4)
C6—C1—C7—C8	5.8 (4)	C13—C12—C17—C18	−179.3 (3)
O1—C7—C8—C9	6.4 (5)	C16—C17—C18—C19	−178.9 (3)
C1—C7—C8—C9	−172.7 (3)	C12—C17—C18—C19	0.8 (4)
C7—C8—C9—C10	179.1 (3)	C17—C18—C19—C10	−0.3 (5)
C8—C9—C10—C11	165.8 (3)	C11—C10—C19—C18	−0.6 (4)
C8—C9—C10—C19	−11.5 (5)	C9—C10—C19—C18	176.8 (3)
C19—C10—C11—C12	1.1 (4)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C10–C12/C17–C19 and C12–C17 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.90 (4)	2.12 (4)	2.974 (4)	159 (4)
N1—H2N1···Cg1ⁱⁱ	0.86 (4)	2.99 (4)	3.475 (3)	118 (3)
C5—H5A···Cg3ⁱⁱⁱ	0.93	2.82	3.513 (3)	132
C11—H11A···Cg3^iv	0.93	2.92	3.631 (3)	135
C13—H13A···Cg2^iv	0.93	2.86	3.551 (3)	132
C16—H16A···Cg1ⁱⁱⁱ	0.93	2.87	3.603 (4)	136

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) x+3/2, −y+1/2, −z+1; (iii) −x−1, y+3/2, −z+5/2; (iv) −x, y+1/2, −z+5/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅NO
M_r	273.32
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	5.7422 (6), 9.8022 (10), 25.504 (3)
V (Å³)	1435.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.32 × 0.28 × 0.07

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.976, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	8109, 1940, 1633
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.119, 1.14
No. of reflections	1940
No. of parameters	198
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.24

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

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C10–C12/C17–C19 and C12–C17 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.90 (4)	2.12 (4)	2.974 (4)	159 (4)
N1—H2N1···Cg1ⁱⁱ	0.86 (4)	2.99 (4)	3.475 (3)	118 (3)
C5—H5A···Cg3ⁱⁱⁱ	0.93	2.82	3.513 (3)	132
C11—H11A···Cg3^iv	0.93	2.92	3.631 (3)	135
C13—H13A···Cg2^iv	0.93	2.86	3.551 (3)	132
C16—H16A···Cg1ⁱⁱⁱ	0.93	2.87	3.603 (4)	136

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) x+3/2, −y+1/2, −z+1; (iii) −x−1, y+3/2, −z+5/2; (iv) −x, y+1/2, −z+5/2.

Footnotes

‡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 the 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

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bandgar, B. P. & Gawande, S. S. (2010). J. Bioorg. Med. Chem. 18, 2060–2065. CrossRef CAS Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cheng, J. H., Hung, C.-F., Yang, S. C., Wang, J.-P., Won, S.-J. & Lin, S.-J. (2008). J. Bioorg. Med. Chem. 16, 7270–7276. CrossRef CAS Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fun, H.-K., Patil, P. S., Dharmaprakash, S. M. & Chantrapromma, S. (2008). Acta Cryst. E64, o1540–o1541. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gaber, M., El-Daly, S. A., Fayed, T. A. & El-Sayed, Y. S. (2008). J. Opt. Laser Techol. 40, 528–537. CrossRef CAS Google Scholar
Horkaew, J., Chantrapromma, S., Saewan, N. & Fun, H.-K. (2010). Acta Cryst. E66, o2346–o2347. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nerya, O., Musa, R., Khatib, S., Tamir, S. & Vaya, J. (2004). Phytochemistry, 65, 1389–1395. Web of Science CrossRef PubMed CAS Google Scholar
Nowakowska, Z., Kedzia, B. & Schroeder, G. (2008). Eur. J. Med. Chem. 43, 707–713. Web of Science CrossRef PubMed CAS Google Scholar
Patil, P. S., Dharmaprakash, S. M., Ramakrishna, K., Fun, H.-K., Kumar, R. S. S. & Narayana Rao, D. (2007). J. Cryst. Growth. 303, 520–524. CrossRef CAS 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
Svetlichny, V. Y., Merola, F., Dobretsov, G. E., Gularyan, S. K. & Syrejshchikova, T. I. (2007). J. Chem. Phys. Lipids, 145, 13–26. Web of Science CrossRef CAS Google Scholar
Tewtrakul, S., Subhadhirasakul, S., Puripattanavong, J. & Panphadung, T. (2003). Songklanakarin J. Sci. Technol. 25, 503–508. CAS Google Scholar
Xu, Z., Bai, G. & Dong, C. (2005). J. Bioorg. Med. Chem. 13, 5694–5699. Web of Science CrossRef CAS Google Scholar

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Volume 67| Part 5| May 2011| Pages o1204-o1205

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