(E)-1-(4-Amino­phen­yl)-3-(2,4,5-trimeth­oxy­phen­yl)prop-2-en-1-one

Fun, H.-K.; Kobkeatthawin, T.; Ruanwas, P.; Chantrapromma, S.

doi:10.1107/S1600536810026346

organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Pages o1973-o1974

https://doi.org/10.1107/S1600536810026346

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(E)-1-(4-Aminophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one

Hoong-Kun Fun,^a ^*‡ Thawanrat Kobkeatthawin,^b Pumsak Ruanwas ^b and Suchada Chantrapromma ^b §

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

(Received 2 July 2010; accepted 4 July 2010; online 10 July 2010)

Molecules of the title aminochalcone, C₁₈H₁₉NO₄, are twisted, with a dihedral angle of 11.26 (6)° between the 4-aminophenyl and 2,4,5-trimethoxyphenyl rings. The conformations of the three methoxy groups with respect to the benzene ring are slightly different. Two methoxy groups are almost coplanar with the attached benzene ring [C—O—C—C torsion angles of −1.45 (19) and 1.5 (2)°], while the third is (−)-synclinal with the attached benzene ring [C—O—C—C = −81.36 (17)°]. In the crystal structure, molecules are stacked into columns along the b axis and molecules in adjacent columns are linked by N—H⋯O hydrogen bonds into V-shaped double columns. Weak π–π interactions are also observed, with a centroid-centroid distance of 3.7532 (8) Å.

Related literature

For bond-length data, see: Allen et al. (1987 ). For hydrogen bond motifs, see: Bernstein et al. (1995 ). For related structures, see: Chantrapromma et al. (2009 , 2010 ); Suwunwong et al. (2009 ). For background to and applications of chalcones, see: Batovska et al. (2007 ); Jung et al. (2008 ); Kim et al. (2010 ); Nielsen et al. (2004 ); Niu et al. (2006 ); Romagnoli et al. (2008 ); Tewtrakul et al. (2003 ); Won et al. (2005 ); Xia et al. (2000 ).

Experimental

Crystal data

C₁₈H₁₉NO₄
M_r = 313.34
Monoclinic, C 2/c
a = 13.6117 (2) Å
b = 10.3540 (2) Å
c = 22.3920 (4) Å
β = 100.879 (1)°
V = 3099.11 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.38 × 0.32 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.965, T_max = 0.991
19818 measured reflections
4506 independent reflections
3581 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.131
S = 1.05
4506 reflections
219 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1ⁱ	0.86 (2)	2.12 (2)	2.9692 (16)	170.4 (17)
N1—H2N1⋯O1ⁱⁱ	0.88 (2)	2.21 (2)	3.0176 (17)	153.4 (19)
Symmetry codes: (i) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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/S1600536810026346/fj2326sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810026346/fj2326Isup2.hkl

checkCIF report

Comment top

Chalcones are important compounds which have considerable interesting applications involving biological activities such as antibacterial (Nielsen et al., 2004), antifungal (Batovska et al., 2007), anti-inflammatory (Won et al., 2005), anti-HIV-1 protease inhibition (Tewtrakul et al., 2003) and antitumor (Romagnoli et al., 2008) properties. Moreover they also show electroactive fluorescent properties (Jung et al., 2008; Niu et al., 2006). From previous reports, aminochalcone showed good cytotoxicity in vitro against human tumor cell lines (Xia et al., 2000) and was a new class of both activator and inhibitor of the TREK2 channel which turn out to be an important channel in charge of tuning neuronal transmitter and hormone levels (Kim et al., 2010). In continuing our on-going research on bioactivity and fluorescence properties of chalcones (Chantrapromma et al., 2009; 2010; Suwunwong et al., 2009), the title aminochalcone (I) was synthesized. (I) doesn't possess antibacterial and cytotoxic activities. However (I) exhibits fluorescence with the maximum emission at 480 nm when the compound is excited at 320 nm in chloroform solution.

The molecule of the title aminochalcone, (Fig. 1), exists in an E configuration with respect to the C8═C9 double bond [1.3407 (19) Å] with torsion angle C7–C8–C9–C10 = 177.99 (13)°. The whole molecule is not planar indicated by the dihedral angle between 4-aminophenyl and 2,4,5-trimethoxyphenyl rings being 11.26 (6)°. The propenone unit (C7—C9/O1) is planar with the r.m.s. deviation 0.0031 (1) Å. The mean plane through the propenone unit makes dihedral angles of 11.70 (9) and 9.19 (9)° respectively with the planes of 4-aminophenyl and 2,4,5-trimethoxyphenyl rings. The three methoxy groups of 2,4,5-trimethoxyphenyl unit have two different orientations: two methoxy groups (at atom C11 and C13 positions) are co-planar with the attached benzene ring with torsion angles C16–O2–C11–C12 = -1.45 (19)° and C17–O3–C13–C12 = 1.5 (2)° whereas the one at atom C14 position is (-)-syn-clinally attached with the torsion angle C18–O4–C14–C13 = -81.36 (17)°. Weak C9—H9A···O1 and C9—H9A···O2 intramolecular interactions generate two S(5) motifs (Bernstein et al., 1995) (Fig. 1 and Table 1). The bond distances and angles are of normal values (Allen et al., 1987) and are comparable with the related structures (Chantrapromma et al., 2009; 2010; Suwunwong et al., 2009).

In the crystal packing (Fig. 2), the molecules are stacked into columns along the b axis. The molecules in the adjacent columns are linked by N—H···O hydrogen bonds (Table 1) into a V-shape double columns. π–π interaction was observed with the Cg₁···Cg₂ distance of 3.7532 (8) Å (symmetry code -1/2 - x, 3/2 - y, 1 - z); Cg₁ and Cg₂ are the centroids of C1–C6 and C10–C15 rings, respectively.

Related literature top

For bond-length data, see: Allen et al. (1987). For hydrogen bond motifs, see: Bernstein et al. (1995). For related structures, see: Chantrapromma et al. (2009, 2010); Suwunwong et al. (2009). For background to and applications of chalcones, see: Batovska et al. (2007); Jung et al. (2008); Kim et al. (2010); Nielsen et al. (2004); Niu et al. (2006); Romagnoli et al. (2008); Tewtrakul et al. (2003); Won et al. (2005); Xia et al. (2000).

Experimental top

The title compound was synthesized by the condensation of 2,4,5-trimethoxybenzaldehyde (0.40 g, 2 mmol) with 4-aminoacetophenone (0.28 g, 2 mmol) in ethanol (30 ml) in the presence of 30% NaOH(aq) (5 ml). After stirring for 3 h at room temperature, the resulting orange solid appeared and was then collected by filtration, washed with distilled water, dried and purified by repeated recrystallization from acetone. Orange block-shaped single crystals of the title compound suitable for x-ray structure determination were recrystallized from acetone by the slow evaporation of the solvent at room temperature after several days, Mp. 393–394 K.

Structure description top

For bond-length data, see: Allen et al. (1987). For hydrogen bond motifs, see: Bernstein et al. (1995). For related structures, see: Chantrapromma et al. (2009, 2010); Suwunwong et al. (2009). For background to and applications of chalcones, see: Batovska et al. (2007); Jung et al. (2008); Kim et al. (2010); Nielsen et al. (2004); Niu et al. (2006); Romagnoli et al. (2008); Tewtrakul et al. (2003); Won et al. (2005); Xia et al. (2000).

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. The dashed lines represent the intramolecular C—H···O interactions.
	Fig. 2. The crystal packing of the title compound viewed along the a axis. Hydrogen bonds are shown as dashed lines.

(E)-1-(4-Aminophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₈H₁₉NO₄	F(000) = 1328
M_r = 313.34	D_x = 1.343 Mg m⁻³
Monoclinic, C2/c	Melting point = 393–394 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 13.6117 (2) Å	Cell parameters from 4506 reflections
b = 10.3540 (2) Å	θ = 1.9–30.0°
c = 22.3920 (4) Å	µ = 0.10 mm⁻¹
β = 100.879 (1)°	T = 100 K
V = 3099.11 (9) Å³	Block, orange
Z = 8	0.38 × 0.32 × 0.10 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4506 independent reflections
Radiation source: sealed tube	3581 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
φ and ω scans	θ_max = 30.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −19→19
T_min = 0.965, T_max = 0.991	k = −14→12
19818 measured reflections	l = −31→31

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0552P)² + 3.4363P] where P = (F_o² + 2F_c²)/3
4506 reflections	(Δ/σ)_max < 0.001
219 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₈H₁₉NO₄	V = 3099.11 (9) Å³
M_r = 313.34	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 13.6117 (2) Å	µ = 0.10 mm⁻¹
b = 10.3540 (2) Å	T = 100 K
c = 22.3920 (4) Å	0.38 × 0.32 × 0.10 mm
β = 100.879 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4506 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3581 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.991	R_int = 0.029
19818 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.43 e Å⁻³
4506 reflections	Δρ_min = −0.23 e Å⁻³
219 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
O1	0.38020 (7)	0.71239 (11)	0.65434 (5)	0.0236 (2)
O2	0.40102 (7)	0.40284 (10)	0.49618 (5)	0.0226 (2)
O3	0.10593 (7)	0.26403 (10)	0.35317 (5)	0.0237 (2)
O4	−0.00667 (7)	0.42294 (10)	0.40878 (5)	0.0230 (2)
N1	0.09228 (9)	1.16277 (13)	0.71073 (6)	0.0226 (3)
H1N1	0.0289 (15)	1.1700 (18)	0.6971 (8)	0.028 (5)*
H2N1	0.1136 (15)	1.197 (2)	0.7468 (9)	0.036 (5)*
C1	0.23640 (9)	0.84035 (13)	0.65403 (6)	0.0165 (3)
C2	0.28745 (9)	0.92608 (13)	0.69789 (6)	0.0169 (3)
H2A	0.3552	0.9129	0.7131	0.020*
C3	0.23973 (10)	1.02891 (13)	0.71892 (6)	0.0174 (3)
H3A	0.2749	1.0829	0.7486	0.021*
C4	0.13779 (10)	1.05267 (13)	0.69558 (6)	0.0171 (3)
C5	0.08494 (9)	0.96364 (14)	0.65447 (6)	0.0183 (3)
H5A	0.0166	0.9746	0.6407	0.022*
C6	0.13318 (10)	0.86001 (14)	0.63425 (6)	0.0182 (3)
H6A	0.0968	0.8020	0.6070	0.022*
C7	0.29247 (10)	0.73650 (13)	0.63014 (6)	0.0177 (3)
C8	0.24234 (10)	0.66396 (14)	0.57644 (6)	0.0201 (3)
H8A	0.1762	0.6835	0.5598	0.024*
C9	0.28853 (9)	0.57075 (13)	0.55064 (6)	0.0177 (3)
H9A	0.3553	0.5549	0.5673	0.021*
C10	0.24334 (9)	0.49221 (13)	0.49882 (6)	0.0163 (3)
C11	0.30112 (9)	0.40495 (13)	0.47178 (6)	0.0174 (3)
C12	0.25784 (10)	0.32686 (13)	0.42310 (6)	0.0185 (3)
H12A	0.2973	0.2697	0.4059	0.022*
C13	0.15546 (10)	0.33465 (13)	0.40038 (6)	0.0181 (3)
C14	0.09645 (9)	0.42119 (13)	0.42698 (6)	0.0181 (3)
C15	0.14011 (10)	0.49721 (13)	0.47490 (6)	0.0177 (3)
H15A	0.1002	0.5538	0.4921	0.021*
C16	0.46300 (10)	0.31421 (15)	0.47127 (7)	0.0227 (3)
H16A	0.5310	0.3231	0.4922	0.034*
H16B	0.4590	0.3324	0.4288	0.034*
H16C	0.4406	0.2276	0.4760	0.034*
C17	0.16178 (11)	0.17238 (15)	0.32512 (7)	0.0249 (3)
H17A	0.1189	0.1338	0.2908	0.037*
H17B	0.1877	0.1065	0.3540	0.037*
H17C	0.2162	0.2155	0.3118	0.037*
C18	−0.04143 (12)	0.49413 (19)	0.35457 (8)	0.0338 (4)
H18A	−0.1129	0.5017	0.3482	0.051*
H18B	−0.0228	0.4500	0.3207	0.051*
H18C	−0.0120	0.5787	0.3582	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0160 (5)	0.0295 (6)	0.0228 (5)	0.0039 (4)	−0.0025 (4)	−0.0032 (4)
O2	0.0130 (4)	0.0288 (6)	0.0253 (5)	0.0038 (4)	0.0019 (4)	−0.0025 (4)
O3	0.0197 (5)	0.0270 (5)	0.0244 (5)	−0.0026 (4)	0.0043 (4)	−0.0092 (4)
O4	0.0132 (4)	0.0286 (6)	0.0263 (5)	−0.0023 (4)	0.0012 (4)	−0.0023 (4)
N1	0.0168 (6)	0.0277 (7)	0.0220 (6)	0.0043 (5)	0.0001 (4)	−0.0045 (5)
C1	0.0151 (6)	0.0176 (6)	0.0160 (6)	−0.0007 (5)	0.0009 (4)	0.0023 (5)
C2	0.0126 (5)	0.0202 (6)	0.0164 (6)	−0.0009 (5)	−0.0009 (4)	0.0036 (5)
C3	0.0157 (6)	0.0201 (6)	0.0151 (6)	−0.0029 (5)	−0.0004 (4)	0.0012 (5)
C4	0.0162 (6)	0.0200 (6)	0.0152 (6)	−0.0005 (5)	0.0035 (4)	0.0034 (5)
C5	0.0116 (5)	0.0230 (7)	0.0195 (6)	−0.0014 (5)	0.0003 (4)	0.0023 (5)
C6	0.0151 (6)	0.0206 (6)	0.0176 (6)	−0.0038 (5)	−0.0002 (4)	0.0006 (5)
C7	0.0160 (6)	0.0194 (6)	0.0170 (6)	−0.0002 (5)	0.0012 (5)	0.0022 (5)
C8	0.0151 (6)	0.0225 (7)	0.0203 (6)	0.0011 (5)	−0.0024 (5)	−0.0015 (5)
C9	0.0137 (5)	0.0220 (7)	0.0170 (6)	−0.0018 (5)	0.0019 (4)	0.0029 (5)
C10	0.0145 (6)	0.0184 (6)	0.0161 (6)	−0.0008 (5)	0.0034 (4)	0.0018 (5)
C11	0.0135 (5)	0.0202 (6)	0.0186 (6)	−0.0002 (5)	0.0034 (5)	0.0035 (5)
C12	0.0178 (6)	0.0186 (6)	0.0209 (6)	0.0013 (5)	0.0080 (5)	0.0005 (5)
C13	0.0190 (6)	0.0186 (6)	0.0174 (6)	−0.0038 (5)	0.0052 (5)	−0.0006 (5)
C14	0.0129 (6)	0.0208 (7)	0.0206 (6)	−0.0023 (5)	0.0033 (5)	0.0008 (5)
C15	0.0148 (6)	0.0187 (6)	0.0200 (6)	0.0003 (5)	0.0045 (5)	−0.0005 (5)
C16	0.0166 (6)	0.0260 (7)	0.0265 (7)	0.0058 (5)	0.0071 (5)	0.0040 (6)
C17	0.0281 (7)	0.0221 (7)	0.0260 (7)	−0.0023 (6)	0.0091 (6)	−0.0064 (6)
C18	0.0208 (7)	0.0432 (10)	0.0345 (9)	0.0005 (7)	−0.0023 (6)	0.0071 (7)

Geometric parameters (Å, º) top

O1—C7	1.2400 (16)	C8—C9	1.3407 (19)
O2—C11	1.3666 (15)	C8—H8A	0.9300
O2—C16	1.4293 (17)	C9—C10	1.4549 (18)
O3—C13	1.3557 (16)	C9—H9A	0.9300
O3—C17	1.4329 (17)	C10—C15	1.4071 (18)
O4—C14	1.3859 (15)	C10—C11	1.4076 (18)
O4—C18	1.4228 (19)	C11—C12	1.3953 (19)
N1—C4	1.3704 (18)	C12—C13	1.3927 (18)
N1—H1N1	0.862 (19)	C12—H12A	0.9300
N1—H2N1	0.88 (2)	C13—C14	1.4083 (19)
C1—C6	1.4060 (18)	C14—C15	1.3724 (19)
C1—C2	1.4064 (18)	C15—H15A	0.9300
C1—C7	1.4760 (19)	C16—H16A	0.9600
C2—C3	1.3758 (19)	C16—H16B	0.9600
C2—H2A	0.9300	C16—H16C	0.9600
C3—C4	1.4089 (18)	C17—H17A	0.9600
C3—H3A	0.9300	C17—H17B	0.9600
C4—C5	1.4016 (19)	C17—H17C	0.9600
C5—C6	1.378 (2)	C18—H18A	0.9600
C5—H5A	0.9300	C18—H18B	0.9600
C6—H6A	0.9300	C18—H18C	0.9600
C7—C8	1.4718 (19)

C11—O2—C16	118.06 (11)	C11—C10—C9	121.02 (12)
C13—O3—C17	118.17 (11)	O2—C11—C12	123.00 (12)
C14—O4—C18	114.38 (11)	O2—C11—C10	115.65 (12)
C4—N1—H1N1	117.0 (13)	C12—C11—C10	121.35 (12)
C4—N1—H2N1	118.4 (13)	C13—C12—C11	119.84 (12)
H1N1—N1—H2N1	115.1 (18)	C13—C12—H12A	120.1
C6—C1—C2	117.47 (12)	C11—C12—H12A	120.1
C6—C1—C7	123.07 (12)	O3—C13—C12	124.72 (12)
C2—C1—C7	119.46 (11)	O3—C13—C14	115.69 (12)
C3—C2—C1	121.63 (12)	C12—C13—C14	119.59 (12)
C3—C2—H2A	119.2	C15—C14—O4	119.17 (12)
C1—C2—H2A	119.2	C15—C14—C13	119.88 (12)
C2—C3—C4	120.24 (12)	O4—C14—C13	120.72 (12)
C2—C3—H3A	119.9	C14—C15—C10	122.04 (12)
C4—C3—H3A	119.9	C14—C15—H15A	119.0
N1—C4—C5	120.65 (12)	C10—C15—H15A	119.0
N1—C4—C3	120.86 (12)	O2—C16—H16A	109.5
C5—C4—C3	118.44 (12)	O2—C16—H16B	109.5
C6—C5—C4	120.69 (12)	H16A—C16—H16B	109.5
C6—C5—H5A	119.7	O2—C16—H16C	109.5
C4—C5—H5A	119.7	H16A—C16—H16C	109.5
C5—C6—C1	121.26 (12)	H16B—C16—H16C	109.5
C5—C6—H6A	119.4	O3—C17—H17A	109.5
C1—C6—H6A	119.4	O3—C17—H17B	109.5
O1—C7—C8	120.93 (12)	H17A—C17—H17B	109.5
O1—C7—C1	120.63 (12)	O3—C17—H17C	109.5
C8—C7—C1	118.43 (11)	H17A—C17—H17C	109.5
C9—C8—C7	122.45 (12)	H17B—C17—H17C	109.5
C9—C8—H8A	118.8	O4—C18—H18A	109.5
C7—C8—H8A	118.8	O4—C18—H18B	109.5
C8—C9—C10	125.73 (12)	H18A—C18—H18B	109.5
C8—C9—H9A	117.1	O4—C18—H18C	109.5
C10—C9—H9A	117.1	H18A—C18—H18C	109.5
C15—C10—C11	117.31 (12)	H18B—C18—H18C	109.5
C15—C10—C9	121.64 (12)

C6—C1—C2—C3	−2.81 (19)	C15—C10—C11—O2	179.96 (11)
C7—C1—C2—C3	176.14 (12)	C9—C10—C11—O2	−1.95 (18)
C1—C2—C3—C4	−1.5 (2)	C15—C10—C11—C12	0.21 (19)
C2—C3—C4—N1	−172.31 (13)	C9—C10—C11—C12	178.30 (12)
C2—C3—C4—C5	5.09 (19)	O2—C11—C12—C13	−179.69 (12)
N1—C4—C5—C6	173.09 (13)	C10—C11—C12—C13	0.0 (2)
C3—C4—C5—C6	−4.31 (19)	C17—O3—C13—C12	1.5 (2)
C4—C5—C6—C1	−0.1 (2)	C17—O3—C13—C14	−178.72 (12)
C2—C1—C6—C5	3.6 (2)	C11—C12—C13—O3	179.60 (13)
C7—C1—C6—C5	−175.30 (13)	C11—C12—C13—C14	−0.2 (2)
C6—C1—C7—O1	−170.62 (13)	C18—O4—C14—C15	104.12 (16)
C2—C1—C7—O1	10.5 (2)	C18—O4—C14—C13	−81.36 (17)
C6—C1—C7—C8	10.37 (19)	O3—C13—C14—C15	−179.72 (12)
C2—C1—C7—C8	−168.52 (12)	C12—C13—C14—C15	0.1 (2)
O1—C7—C8—C9	−1.0 (2)	O3—C13—C14—O4	5.79 (19)
C1—C7—C8—C9	177.98 (13)	C12—C13—C14—O4	−174.38 (12)
C7—C8—C9—C10	177.99 (13)	O4—C14—C15—C10	174.73 (12)
C8—C9—C10—C15	−7.9 (2)	C13—C14—C15—C10	0.2 (2)
C8—C9—C10—C11	174.10 (14)	C11—C10—C15—C14	−0.3 (2)
C16—O2—C11—C12	−1.45 (19)	C9—C10—C15—C14	−178.39 (13)
C16—O2—C11—C10	178.80 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.86 (2)	2.12 (2)	2.9692 (16)	170.4 (17)
N1—H2N1···O1ⁱⁱ	0.88 (2)	2.21 (2)	3.0176 (17)	153.4 (19)

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₉NO₄
M_r	313.34
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	13.6117 (2), 10.3540 (2), 22.3920 (4)
β (°)	100.879 (1)
V (Å³)	3099.11 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.38 × 0.32 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.965, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	19818, 4506, 3581
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.131, 1.05
No. of reflections	4506
No. of parameters	219
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.23

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
N1—H1N1···O1ⁱ	0.86 (2)	2.12 (2)	2.9692 (16)	170.4 (17)
N1—H2N1···O1ⁱⁱ	0.88 (2)	2.21 (2)	3.0176 (17)	153.4 (19)

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.

Acknowledgements

The authors thank the Thailand Research Fund (TRF) for the research grant (RSA5280033), Prince of Songkla University and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. TK and PR thank the Graduate School, Prince of Songkla University, for partial financial support.

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