(2E)-1-(Pyridin-2-yl)-3-(2,4,6-trimeth­oxy­phen­yl)prop-2-en-1-one

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

doi:10.1107/S1600536811039110

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Pages o2789-o2790

https://doi.org/10.1107/S1600536811039110

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(2E)-1-(Pyridin-2-yl)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one

Hoong-Kun Fun,^a ^*‡ Suchada Chantrapromma ^b § and Thitipone Suwunwong ^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 19 September 2011; accepted 23 September 2011; online 30 September 2011)

The title heteroaryl chalcone derivative, C₁₇H₁₇NO₄, is a condensation product of 2-acetylpyridine and 2,4,6-trimethoxybenzaldehyde. The molecule is roughly planar, the dihedral angle between the pyridine and benzene rings being 5.51 (10)°. All the three methoxy groups are almost co-planar with the bound benzene ring [r.m.s. deviation of 0.0306 (2) Å]. A weak C—H⋯O intramolecular interaction involving one of the ortho-methoxy groups generates an S(6) ring motif. In the crystal, the molecules are linked by weak C—H⋯O interactions into anti-parallel face-to-face pairs. Adjacent pairs are further connected into sheets parallel to the ab plane.

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 ); Fun et al. (2010 , 2011 ). For background to and applications of chalcones and heteroaryl chalcones, see: Bandgar et al. (2010 ); Gacche et al. (2008 ); Go et al. (2005 ); Isomoto et al. (2005 ); Jung et al. (2008 ); Suwunwong et al. (2011 ); Tewtrakul et al. (2003 ). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ).

Experimental

Crystal data

C₁₇H₁₇NO₄
M_r = 299.32
Orthorhombic, F d d 2
a = 31.563 (2) Å
b = 44.508 (3) Å
c = 3.9504 (3) Å
V = 5549.6 (7) Å³
Z = 16
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.58 × 0.14 × 0.04 mm

Data collection

Bruker APEXII CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.943, T_max = 0.996
31465 measured reflections
2309 independent reflections
1908 reflections with I > 2σ(I)
R_int = 0.100

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.105
S = 1.09
2309 reflections
267 parameters
1 restraint
All H-atom parameters refined
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O2ⁱ	1.00 (2)	2.45 (3)	3.369 (2)	157.8 (17)
C7—H11B⋯O4	0.97 (3)	2.31 (2)	2.835 (2)	113.1 (18)
C17—H17B⋯O4ⁱⁱ	0.99 (2)	2.46 (2)	3.337 (3)	148 (2)
Symmetry codes: (i) $[x+{\script{9\over 4}}, -y+{\script{9\over 4}}, z+{\script{1\over 4}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y, z-{\script{1\over 2}}]$ .

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/S1600536811039110/rz2642sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811039110/rz2642Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811039110/rz2642Isup3.cml

checkCIF report

Comment top

Chalcones and heteroaryl chalcones have drawn a lot of interests due to their wide range of biological properties including antioxidant (Gacche et al., 2008), antibacterial (Go et al., 2005; Isomoto et al., 2005), anti-inflammatory and anticancer (Bandgar et al., 2010) as well as HIV-1 protease inhibitory (Tewtrakul et al., 2003) activities. Furthermore they also exhibit fluorescent property (Jung et al., 2008; Suwunwong et al., 2011). In our on-going research on the biological and fluorescent properties of chalcones and heteroaryl chalcones (Chantrapromma et al., 2009; Fun et al., 2010, 2011; Suwunwong et al., 2011), the title heteroaryl chalcone derivative (I) was synthesized in order to study the effects of substituted positions on the fluorescent property in comparision with the closely related compounds (Fun et al., 2011; Suwunwong et al., 2011). In addition (I) was also tested for analgesic and antibacterial activities. Our results showed that (I) exhibits a moderate analgesic activity but is inactive for antibacterial activity. Herein we report the crystal structure of (I).

The molecule of the title heteroaryl chalcone derivative (Fig. 1) exists in an E configuration with respect to the C7═C8 double bond [1.341 (3) Å]. The torsion angle C6–C7–C8–C9 is 179.0 (2)°. The molecule is almost planar with a dihedral angle between the pyridine and 2,4,6-trimethoxyphenyl rings of 5.51 (10)°. Atoms of the propenone bridge (C6, C7, C8 and O1) lie on the same plane [r.m.s. deviation of 0.017 (2)] and the torsion angle O1–C6–C7–C8 is -5.8 (4)°. The mean plane through this bridge makes dihedral angles of 6.96 (16) and 11.72 (16)° with the planes of pyridine and benzene rings, respectively. All the three substituted methoxy groups of the 2,4,6-trimethoxyphenyl unit are co-planar with the phenyl ring as indicated by the torsion angles C15–O2–C10–C11 = -0.4 (3)°, C16–O3–C12–C13 = 0.9 (3)° and C17–O4–C14–C13 = -4.7 (3)°. In the molecule, a weak intramolecular C7—H7A···O4 interaction (Table 1) generates an S(6) ring motif (Bernstein et al., 1995). The bond distances are of normal values (Allen et al., 1987) and comparable with related structures (Chantrapromma et al., 2009; Fun et al., 2010; 2011).

In the crystal packing (Fig. 2), only the two ortho-methoxy groups are involved in weak C—H···O interactions (Table 1). The adjacent molecules are linked by weak C17—H17B···O4 interaction (Table 1) into anti-parallel face-to-face pairs. The adjacent pairs were further connected by weak C3—H3A···O2 interactions (Table 1) into sheets parallel to the ab plane which are stacked down the c axis. The crystal may be further stabilized by C···O [3.203 (2) Å] short contacts.

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); Fun et al. (2010, 2011). For background to and applications of chalcones and heteroaryl chalcones, see: Bandgar et al. (2010); Gacche et al. (2008); Go et al. (2005); Isomoto et al. (2005); Jung et al. (2008); Suwunwong et al. (2011); Tewtrakul et al. (2003). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986).

Experimental top

The title compound was synthesized by the condensation reaction of 2,4,6-trimethoxybenzaldehyde (0.40 g, 2 mmol) with 2-acetylpyridine (0.20 g, 2 mmol) in ethanol (30 ml) in the presence of 30% NaOH(aq) (5 ml). After stirring in ice bath at 278 K for 4 h, the resulting pale yellow solid appeared and was then collected by filtration, washed with distilled water, dried and purified by repeated recrystallization from acetone. Pale yellow plate-shaped single crystals of the title compound suitable for X-ray structure determination were recrystalized from acetone/ethanol (1:1 v/v) by the evaporation of the solvent at room temperature after several days, M.p. 392-393 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); Fun et al. (2010, 2011). For background to and applications of chalcones and heteroaryl chalcones, see: Bandgar et al. (2010); Gacche et al. (2008); Go et al. (2005); Isomoto et al. (2005); Jung et al. (2008); Suwunwong et al. (2011); Tewtrakul et al. (2003). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986).

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. A weak intramolecular C—H···O interaction is shown as a dashed line.
	Fig. 2. The crystal packing of the title compound viewed along the c axis, showing molecular sheets parallel to the ab plane. Hydrogen bonds are shown as dashed lines.

(2E)-1-(Pyridin-2-yl)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₇H₁₇NO₄	D_x = 1.433 Mg m⁻³
M_r = 299.32	Melting point = 392–393 K
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 2309 reflections
a = 31.563 (2) Å	θ = 1.6–30.0°
b = 44.508 (3) Å	µ = 0.10 mm⁻¹
c = 3.9504 (3) Å	T = 100 K
V = 5549.6 (7) Å³	Plate, pale yellow
Z = 16	0.58 × 0.14 × 0.04 mm
F(000) = 2528

Data collection top

Bruker APEXII CCD area detector diffractometer	2309 independent reflections
Radiation source: sealed tube	1908 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.100
φ and ω scans	θ_max = 30.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −44→44
T_min = 0.943, T_max = 0.996	k = −62→62
31465 measured reflections	l = −5→5

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	All H-atom parameters refined
S = 1.09	w = 1/[σ²(F_o²) + (0.0467P)² + 4.8268P] where P = (F_o² + 2F_c²)/3
2309 reflections	(Δ/σ)_max = 0.001
267 parameters	Δρ_max = 0.23 e Å⁻³
1 restraint	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₇H₁₇NO₄	V = 5549.6 (7) Å³
M_r = 299.32	Z = 16
Orthorhombic, Fdd2	Mo Kα radiation
a = 31.563 (2) Å	µ = 0.10 mm⁻¹
b = 44.508 (3) Å	T = 100 K
c = 3.9504 (3) Å	0.58 × 0.14 × 0.04 mm

Data collection top

Bruker APEXII CCD area detector diffractometer	2309 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1908 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.996	R_int = 0.100
31465 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	1 restraint
wR(F²) = 0.105	All H-atom parameters refined
S = 1.09	Δρ_max = 0.23 e Å⁻³
2309 reflections	Δρ_min = −0.27 e Å⁻³
267 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 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
O1	0.18610 (5)	0.11217 (3)	1.2030 (5)	0.0298 (4)
O2	0.07115 (4)	0.04799 (3)	1.1758 (5)	0.0239 (3)
O3	0.05980 (4)	−0.04831 (3)	0.6752 (5)	0.0248 (4)
O4	0.19307 (4)	0.00496 (3)	0.6918 (5)	0.0242 (4)
N1	0.27419 (5)	0.08486 (4)	0.7393 (6)	0.0245 (4)
C1	0.31419 (7)	0.09271 (5)	0.6662 (7)	0.0263 (5)
C2	0.33299 (7)	0.11932 (5)	0.7701 (7)	0.0266 (5)
C3	0.30912 (7)	0.13912 (5)	0.9612 (7)	0.0270 (5)
C4	0.26779 (7)	0.13153 (5)	1.0406 (7)	0.0254 (5)
C5	0.25139 (6)	0.10419 (4)	0.9256 (7)	0.0225 (4)
C6	0.20685 (6)	0.09511 (4)	1.0251 (7)	0.0226 (4)
C7	0.19132 (7)	0.06578 (4)	0.9048 (7)	0.0228 (4)
C8	0.15391 (7)	0.05521 (4)	1.0129 (7)	0.0228 (4)
C9	0.13222 (6)	0.02737 (4)	0.9251 (6)	0.0213 (4)
C10	0.08883 (6)	0.02411 (4)	1.0100 (6)	0.0217 (4)
C11	0.06569 (6)	−0.00125 (4)	0.9267 (7)	0.0225 (4)
C12	0.08555 (6)	−0.02465 (4)	0.7554 (6)	0.0216 (4)
C13	0.12828 (6)	−0.02332 (4)	0.6760 (7)	0.0220 (4)
C14	0.15094 (6)	0.00253 (4)	0.7601 (6)	0.0217 (4)
C15	0.02726 (7)	0.04603 (5)	1.2600 (7)	0.0252 (5)
C16	0.07863 (7)	−0.07331 (5)	0.5027 (7)	0.0259 (5)
C17	0.21410 (7)	−0.02095 (5)	0.5537 (7)	0.0261 (5)
H1A	0.3305 (7)	0.0785 (5)	0.524 (8)	0.023 (6)*
H2A	0.3622 (7)	0.1239 (5)	0.708 (9)	0.027 (6)*
H3A	0.3216 (7)	0.1581 (5)	1.051 (8)	0.025 (6)*
H4A	0.2489 (7)	0.1445 (5)	1.187 (9)	0.030 (7)*
H8A	0.1375 (8)	0.0676 (6)	1.166 (9)	0.039 (8)*
H11A	0.0350 (7)	−0.0029 (5)	0.980 (8)	0.023 (6)*
H11B	0.2095 (7)	0.0554 (5)	0.747 (9)	0.025 (6)*
H13A	0.1415 (7)	−0.0402 (5)	0.545 (8)	0.025 (6)*
H15A	0.0101 (8)	0.0457 (6)	1.054 (9)	0.033 (8)*
H15B	0.0223 (8)	0.0281 (6)	1.428 (10)	0.038 (7)*
H15C	0.0194 (7)	0.0634 (5)	1.389 (8)	0.024 (7)*
H16A	0.0549 (7)	−0.0874 (5)	0.453 (8)	0.023 (6)*
H16B	0.0916 (7)	−0.0668 (5)	0.282 (9)	0.023 (6)*
H16C	0.1003 (8)	−0.0827 (5)	0.644 (9)	0.031 (7)*
H17A	0.2010 (8)	−0.0257 (6)	0.328 (9)	0.030 (8)*
H17B	0.2445 (7)	−0.0160 (5)	0.542 (8)	0.025 (6)*
H17C	0.2105 (7)	−0.0383 (5)	0.714 (9)	0.028 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0320 (8)	0.0216 (7)	0.0360 (11)	−0.0005 (6)	0.0043 (8)	−0.0058 (8)
O2	0.0246 (7)	0.0189 (6)	0.0283 (9)	0.0001 (5)	0.0026 (7)	−0.0024 (7)
O3	0.0251 (7)	0.0175 (6)	0.0317 (10)	−0.0026 (5)	0.0018 (7)	−0.0032 (7)
O4	0.0236 (7)	0.0194 (6)	0.0295 (10)	−0.0009 (5)	0.0026 (7)	−0.0034 (7)
N1	0.0284 (9)	0.0189 (8)	0.0264 (11)	0.0003 (6)	−0.0011 (8)	−0.0007 (8)
C1	0.0279 (10)	0.0233 (9)	0.0276 (13)	0.0008 (8)	0.0002 (10)	0.0019 (10)
C2	0.0290 (11)	0.0239 (9)	0.0270 (13)	−0.0012 (8)	−0.0014 (10)	0.0061 (10)
C3	0.0320 (11)	0.0203 (9)	0.0288 (14)	−0.0037 (8)	−0.0050 (11)	0.0023 (10)
C4	0.0313 (11)	0.0197 (9)	0.0251 (12)	−0.0004 (8)	−0.0021 (10)	0.0009 (9)
C5	0.0274 (10)	0.0188 (9)	0.0214 (11)	−0.0013 (7)	−0.0012 (9)	0.0033 (9)
C6	0.0267 (10)	0.0185 (9)	0.0224 (11)	0.0004 (7)	−0.0010 (9)	0.0029 (9)
C7	0.0278 (10)	0.0162 (9)	0.0242 (12)	0.0008 (7)	−0.0007 (9)	0.0012 (9)
C8	0.0266 (10)	0.0173 (8)	0.0245 (12)	0.0013 (7)	−0.0014 (9)	0.0017 (9)
C9	0.0258 (10)	0.0181 (9)	0.0200 (12)	0.0013 (7)	−0.0009 (9)	0.0019 (9)
C10	0.0287 (10)	0.0162 (8)	0.0201 (11)	0.0015 (7)	−0.0017 (9)	0.0011 (9)
C11	0.0233 (9)	0.0195 (9)	0.0248 (12)	0.0001 (7)	0.0002 (9)	0.0027 (9)
C12	0.0287 (10)	0.0156 (8)	0.0206 (12)	−0.0024 (7)	−0.0039 (9)	0.0021 (8)
C13	0.0263 (10)	0.0176 (8)	0.0220 (12)	−0.0009 (7)	−0.0012 (9)	−0.0009 (9)
C14	0.0245 (10)	0.0191 (9)	0.0214 (12)	0.0007 (7)	−0.0014 (9)	0.0028 (9)
C15	0.0247 (10)	0.0231 (9)	0.0279 (13)	0.0018 (8)	0.0003 (10)	−0.0022 (10)
C16	0.0305 (11)	0.0179 (9)	0.0292 (13)	−0.0016 (8)	−0.0011 (10)	−0.0026 (10)
C17	0.0264 (11)	0.0194 (9)	0.0325 (14)	0.0009 (8)	0.0045 (10)	−0.0029 (10)

Geometric parameters (Å, º) top

O1—C6	1.224 (3)	C7—H11B	0.96 (3)
O2—C10	1.368 (2)	C8—C9	1.458 (3)
O2—C15	1.427 (3)	C8—H8A	0.97 (3)
O3—C12	1.367 (2)	C9—C14	1.413 (3)
O3—C16	1.434 (3)	C9—C10	1.417 (3)
O4—C14	1.361 (2)	C10—C11	1.384 (3)
O4—C17	1.438 (3)	C11—C12	1.392 (3)
N1—C5	1.341 (3)	C11—H11A	0.99 (2)
N1—C1	1.342 (3)	C12—C13	1.386 (3)
C1—C2	1.387 (3)	C13—C14	1.395 (3)
C1—H1A	0.99 (3)	C13—H13A	1.00 (3)
C2—C3	1.383 (3)	C15—H15A	0.98 (3)
C2—H2A	0.97 (2)	C15—H15B	1.05 (3)
C3—C4	1.384 (3)	C15—H15C	0.96 (3)
C3—H3A	1.00 (2)	C16—H16A	1.00 (2)
C4—C5	1.398 (3)	C16—H16B	1.01 (3)
C4—H4A	1.01 (3)	C16—H16C	0.98 (3)
C5—C6	1.515 (3)	C17—H17A	1.01 (3)
C6—C7	1.474 (3)	C17—H17B	0.99 (2)
C7—C8	1.341 (3)	C17—H17C	1.00 (3)

C10—O2—C15	117.39 (16)	O2—C10—C9	115.35 (17)
C12—O3—C16	117.48 (16)	C11—C10—C9	122.49 (19)
C14—O4—C17	117.55 (16)	C10—C11—C12	119.22 (19)
C5—N1—C1	117.13 (18)	C10—C11—H11A	121.7 (14)
N1—C1—C2	124.1 (2)	C12—C11—H11A	119.1 (14)
N1—C1—H1A	116.3 (13)	O3—C12—C13	123.98 (18)
C2—C1—H1A	119.5 (13)	O3—C12—C11	114.91 (18)
C3—C2—C1	118.2 (2)	C13—C12—C11	121.11 (18)
C3—C2—H2A	121.2 (15)	C12—C13—C14	118.69 (19)
C1—C2—H2A	120.6 (15)	C12—C13—H13A	119.3 (13)
C2—C3—C4	118.8 (2)	C14—C13—H13A	121.8 (13)
C2—C3—H3A	121.3 (14)	O4—C14—C13	121.27 (19)
C4—C3—H3A	119.8 (14)	O4—C14—C9	115.97 (17)
C3—C4—C5	119.2 (2)	C13—C14—C9	122.75 (18)
C3—C4—H4A	123.1 (13)	O2—C15—H15A	110.2 (17)
C5—C4—H4A	117.7 (13)	O2—C15—H15B	109.8 (14)
N1—C5—C4	122.54 (19)	H15A—C15—H15B	115 (2)
N1—C5—C6	117.99 (17)	O2—C15—H15C	109.0 (14)
C4—C5—C6	119.4 (2)	H15A—C15—H15C	108 (2)
O1—C6—C7	123.82 (19)	H15B—C15—H15C	104 (2)
O1—C6—C5	118.70 (18)	O3—C16—H16A	105.8 (14)
C7—C6—C5	117.47 (19)	O3—C16—H16B	111.0 (14)
C8—C7—C6	120.1 (2)	H16A—C16—H16B	108 (2)
C8—C7—H11B	124.1 (14)	O3—C16—H16C	110.5 (17)
C6—C7—H11B	115.8 (14)	H16A—C16—H16C	112 (2)
C7—C8—C9	129.5 (2)	H16B—C16—H16C	109 (2)
C7—C8—H8A	118.2 (15)	O4—C17—H17A	108.4 (15)
C9—C8—H8A	112.3 (15)	O4—C17—H17B	106.7 (14)
C14—C9—C10	115.68 (17)	H17A—C17—H17B	114 (2)
C14—C9—C8	125.35 (18)	O4—C17—H17C	109.0 (16)
C10—C9—C8	118.97 (18)	H17A—C17—H17C	111 (2)
O2—C10—C11	122.16 (18)	H17B—C17—H17C	108 (2)

C5—N1—C1—C2	−0.2 (4)	C8—C9—C10—O2	−1.0 (3)
N1—C1—C2—C3	0.0 (4)	C14—C9—C10—C11	−2.2 (3)
C1—C2—C3—C4	0.1 (4)	C8—C9—C10—C11	178.1 (2)
C2—C3—C4—C5	−0.1 (4)	O2—C10—C11—C12	179.5 (2)
C1—N1—C5—C4	0.3 (3)	C9—C10—C11—C12	0.5 (4)
C1—N1—C5—C6	−177.1 (2)	C16—O3—C12—C13	0.9 (3)
C3—C4—C5—N1	−0.1 (4)	C16—O3—C12—C11	−179.1 (2)
C3—C4—C5—C6	177.2 (2)	C10—C11—C12—O3	−178.1 (2)
N1—C5—C6—O1	178.0 (2)	C10—C11—C12—C13	1.9 (4)
C4—C5—C6—O1	0.5 (3)	O3—C12—C13—C14	177.6 (2)
N1—C5—C6—C7	−1.1 (3)	C11—C12—C13—C14	−2.3 (3)
C4—C5—C6—C7	−178.5 (2)	C17—O4—C14—C13	−4.7 (3)
O1—C6—C7—C8	−5.8 (4)	C17—O4—C14—C9	174.2 (2)
C5—C6—C7—C8	173.2 (2)	C12—C13—C14—O4	179.2 (2)
C6—C7—C8—C9	179.0 (2)	C12—C13—C14—C9	0.4 (3)
C7—C8—C9—C14	14.7 (4)	C10—C9—C14—O4	−177.1 (2)
C7—C8—C9—C10	−165.6 (2)	C8—C9—C14—O4	2.6 (3)
C15—O2—C10—C11	−0.4 (3)	C10—C9—C14—C13	1.8 (3)
C15—O2—C10—C9	178.7 (2)	C8—C9—C14—C13	−178.6 (2)
C14—C9—C10—O2	178.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2ⁱ	1.00 (2)	2.45 (3)	3.369 (2)	157.8 (17)
C7—H11B···O4	0.97 (3)	2.31 (2)	2.835 (2)	113.1 (18)
C17—H17B···O4ⁱⁱ	0.99 (2)	2.46 (2)	3.337 (3)	148 (2)

Symmetry codes: (i) x+9/4, −y+9/4, z+1/4; (ii) −x+1/2, −y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇NO₄
M_r	299.32
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	100
a, b, c (Å)	31.563 (2), 44.508 (3), 3.9504 (3)
V (Å³)	5549.6 (7)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.58 × 0.14 × 0.04

Data collection
Diffractometer	Bruker APEXII CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.943, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	31465, 2309, 1908
R_int	0.100
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.105, 1.09
No. of reflections	2309
No. of parameters	267
No. of restraints	1
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.27

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
C3—H3A···O2ⁱ	1.00 (2)	2.45 (3)	3.369 (2)	157.8 (17)
C7—H11B···O4	0.97 (3)	2.31 (2)	2.835 (2)	113.1 (18)
C17—H17B···O4ⁱⁱ	0.99 (2)	2.46 (2)	3.337 (3)	148 (2)

Symmetry codes: (i) x+9/4, −y+9/4, z+1/4; (ii) −x+1/2, −y, z−1/2.

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 (grant No. RSA5280033) and Prince of Songkla University for financial support. They also thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. Mr Teerasak Anantapong, Department of Biotechnology, Faculty of Agro-Industry, Prince of Songkla University, is acknowledged for the bacterial assay.

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