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

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

doi:10.1107/S1600536813015821

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 7| July 2013| Pages o1076-o1077

https://doi.org/10.1107/S1600536813015821

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

Suchada Chantrapromma,^a ^*‡ Thitipone Suwunwong,^a Nawong Boonnak ^b and Hoong-Kun Fun ^c,^d §

^aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^bFaculty of Traditional Thai Medicine, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^dDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia
^*Correspondence e-mail: suchada.c@psu.ac.th

(Received 6 June 2013; accepted 6 June 2013; online 12 June 2013)

The title heteroaryl chalcone derivative, C₁₇H₁₇NO₄, is close to planar: the dihedral angle between the pyridine and benzene rings is 3.71 (11)° and the methoxy C atoms deviate from their attached ring by 0.046 (3), −0.044 (2) and 0.127 (3) Å. The disposition of the pyridine N atom and the carbonyl group is anti [N—C—C—O = −177.7 (2)°]. In the crystal, molecules are linked by weak C—H⋯N and C—H⋯O interactions into (100) sheets and an aromatic π–π stacking interaction between the pyridine and benzene ring, with a centroid–centroid separation of 3.7036 (14) Å also occurs.

Related literature

For the fluorescence properties of heteroaryl chalcones, see: Suwunwong et al. (2011 ). For related structures, see: Chantrapromma et al. (2009 ); Fun et al. (2010 , 2011 ); Suwunwong et al. (2012 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₇H₁₇NO₄
M_r = 299.32
Monoclinic, P 2₁ /c
a = 8.4047 (3) Å
b = 8.7285 (3) Å
c = 19.5086 (7) Å
β = 94.113 (2)°
V = 1427.47 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.32 × 0.27 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.969, T_max = 0.984
14970 measured reflections
3792 independent reflections
2435 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.188
S = 1.07
3792 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O4ⁱ	0.93	2.39	3.277 (3)	160
C15—H15A⋯N1ⁱⁱ	0.96	2.47	3.349 (3)	153
Symmetry codes: (i) $[x-1, -y+{\script{5\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y-1, z.

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, PLATON (Spek, 2009 ), Mercury (Macrae et al., 2006 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813015821/hb7090sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813015821/hb7090Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813015821/hb7090Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of the crystal structures and fluorescent properties of chalcones and heteroaryl chalcones (Chantrapromma et al., 2009; Fun et al., 2010, 2011; Suwunwong et al., 2011, 2012), the title heteroaryl chalcone derivative (I) was synthesized and studied for fluorescent property and for further cyclization purpose. It was also screened for antibacterial and antityrosinase activities and found to be inactive. However it exhibited fluorescence with the emission wavelength at 530 nm when excited at 401 nm. Herein we report the crystal structure of (I).

The molecule of the title heteroaryl chalcone (Fig. 1) exists in an E conformation with respect to the C7═C8 double bond [1.343 (3) Å] and the torsion angle C6–C7–C8–C9 = 179.4 (2)°. The molecule is close to planar with the dihedral angle between pyridine and benzene rings being 3.71 (11)°. Atoms of the middle propenone bridge (C6, C7, C8 and O1) lie almost on the same plane as indicated by the torsion angle O1–C6–C7–C8 = -1.3 (4)°. The mean plane through this bridge makes dihedral angles of 3.03 (15) and 3.06 (15)° with the planes of pyridine and benzene rings, respectively. All the three substituted methoxy groups of 2,4,5-trimethoxyphenyl unit are close to co-planar with the bound benzene ring with the r.m.s. deviation of 0.0290 (2) Å for the twelve non H atoms and the torsion angles C15–O2–C10–C11 = 0.4 (3)°, C16–O3–C12–C13 = 177.9 (2)° and C17–O4–C13–C14 = -2.6 (3)°. The bond distances are comparable with those in related structures (Chantrapromma et al., 2009; Fun et al., 2010; 2011 and Suwunwong et al., 2012).

In the crystal (Fig. 2), only one methoxy group (at atom C10) is involved in weak C—H···N and C—H···O interactions (Table 1). The molecules are linked by weak C15—H15A···N1 and C3—H3A···O4 interactions (Table 1) into (100) sheets. π–π interaction with the Cg₁···Cg₂ⁱⁱⁱ distance of 3.7036 (14) Å (iii = 2 - x, 2 - y, -z) was presented (Fig. 3); Cg₁ and Cg₂ are the centroids of N1/C1–C5 and C9–C14 rings, respectively.

Related literature top

For the fluorescence properties of heteroaryl chalcones, see: Suwunwong et al. (2011). For related structures, see: Chantrapromma et al. (2009); Fun et al. (2010, 2011); Suwunwong et al. (2012). 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 of 2,4,5-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 yellow solid appeared and was then collected by filtration, washed with distilled water, dried and purified by repeated recrystallization from acetone. Yellow blocks of (I) were recrystallized from acetone solution by the slow evaporation of the solvent at room temperature after several days, Mp. 428–429 K.

Structure description top

For the fluorescence properties of heteroaryl chalcones, see: Suwunwong et al. (2011). For related structures, see: Chantrapromma et al. (2009); Fun et al. (2010, 2011); Suwunwong et al. (2012). 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), PLATON (Spek, 2009), Mercury (Macrae et al., 2006) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of (I) viewed along the a axis, showing molecular sheets parallel to the bc plane. C—H···O and C—H···N interactions are shown as dashed lines.
	Fig. 3. The crystal packing of (I) viewed approximately along the b axis, showing π–π interactions; Cg₁ and Cg₂ are the centroids of N1/C1–C5 and C9–C14 rings, respectively. H atoms were omitted for clarity.

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

Crystal data top

C₁₇H₁₇NO₄	F(000) = 632
M_r = 299.32	D_x = 1.393 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 428–429 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.4047 (3) Å	Cell parameters from 3792 reflections
b = 8.7285 (3) Å	θ = 2.1–29.0°
c = 19.5086 (7) Å	µ = 0.10 mm⁻¹
β = 94.113 (2)°	T = 100 K
V = 1427.47 (9) Å³	Block, yellow
Z = 4	0.32 × 0.27 × 0.16 mm

Data collection top

Bruker APEXII CCD diffractometer	3792 independent reflections
Radiation source: sealed tube	2435 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
φ and ω scans	θ_max = 29.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→11
T_min = 0.969, T_max = 0.984	k = −11→11
14970 measured reflections	l = −26→26

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.188	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0802P)² + 1.2643P] where P = (F_o² + 2F_c²)/3
3792 reflections	(Δ/σ)_max = 0.001
202 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₇H₁₇NO₄	V = 1427.47 (9) Å³
M_r = 299.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.4047 (3) Å	µ = 0.10 mm⁻¹
b = 8.7285 (3) Å	T = 100 K
c = 19.5086 (7) Å	0.32 × 0.27 × 0.16 mm
β = 94.113 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3792 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2435 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.984	R_int = 0.054
14970 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.188	H-atom parameters constrained
S = 1.07	Δρ_max = 0.58 e Å⁻³
3792 reflections	Δρ_min = −0.29 e Å⁻³
202 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	0.6126 (2)	0.93348 (19)	−0.05940 (8)	0.0229 (4)
O2	0.9130 (2)	0.60091 (19)	0.09428 (8)	0.0234 (4)
O3	1.3110 (2)	0.78070 (19)	0.26882 (8)	0.0219 (4)
O4	1.2622 (2)	1.05914 (19)	0.22949 (8)	0.0234 (4)
N1	0.7107 (2)	1.3210 (2)	−0.02122 (10)	0.0194 (4)
C1	0.6314 (3)	1.2048 (3)	−0.05320 (11)	0.0166 (5)
C2	0.5113 (3)	1.2269 (3)	−0.10560 (12)	0.0221 (5)
H2A	0.4597	1.1436	−0.1270	0.027*
C3	0.4706 (3)	1.3755 (3)	−0.12499 (12)	0.0239 (5)
H3A	0.3901	1.3938	−0.1592	0.029*
C4	0.5517 (3)	1.4957 (3)	−0.09262 (12)	0.0234 (5)
H4A	0.5276	1.5964	−0.1050	0.028*
C5	0.6702 (3)	1.4634 (3)	−0.04114 (12)	0.0222 (5)
H5A	0.7241	1.5450	−0.0194	0.027*
C6	0.6774 (3)	1.0442 (3)	−0.03057 (11)	0.0184 (5)
C7	0.7993 (3)	1.0306 (3)	0.02671 (11)	0.0214 (5)
H7A	0.8459	1.1188	0.0459	0.026*
C8	0.8451 (3)	0.8932 (3)	0.05195 (11)	0.0199 (5)
H8A	0.7949	0.8080	0.0315	0.024*
C9	0.9661 (3)	0.8631 (3)	0.10836 (11)	0.0178 (5)
C10	0.9984 (3)	0.7123 (3)	0.12964 (11)	0.0172 (5)
C11	1.1109 (3)	0.6809 (3)	0.18425 (11)	0.0165 (5)
H11A	1.1281	0.5805	0.1989	0.020*
C12	1.1961 (3)	0.7987 (3)	0.21634 (11)	0.0173 (5)
C13	1.1689 (3)	0.9518 (3)	0.19514 (11)	0.0176 (5)
C14	1.0550 (3)	0.9814 (3)	0.14248 (11)	0.0177 (5)
H14A	1.0361	1.0824	0.1290	0.021*
C15	0.9402 (3)	0.4457 (3)	0.11480 (13)	0.0268 (6)
H15A	0.8753	0.3791	0.0853	0.040*
H15B	0.9130	0.4327	0.1614	0.040*
H15C	1.0507	0.4207	0.1115	0.040*
C16	1.3405 (3)	0.6280 (3)	0.29434 (12)	0.0230 (5)
H16A	1.4170	0.6315	0.3333	0.035*
H16B	1.3814	0.5662	0.2589	0.035*
H16C	1.2427	0.5844	0.3079	0.035*
C17	1.2442 (3)	1.2141 (3)	0.20699 (13)	0.0248 (5)
H17A	1.3223	1.2770	0.2319	0.037*
H17B	1.1392	1.2497	0.2153	0.037*
H17C	1.2590	1.2199	0.1587	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0286 (9)	0.0155 (9)	0.0246 (8)	−0.0034 (7)	0.0011 (7)	−0.0018 (7)
O2	0.0307 (10)	0.0092 (8)	0.0283 (8)	−0.0006 (7)	−0.0102 (7)	0.0001 (7)
O3	0.0235 (9)	0.0135 (8)	0.0271 (8)	0.0002 (7)	−0.0089 (7)	0.0034 (7)
O4	0.0269 (9)	0.0110 (9)	0.0307 (9)	−0.0018 (7)	−0.0094 (7)	0.0017 (7)
N1	0.0240 (10)	0.0142 (10)	0.0199 (9)	0.0012 (8)	0.0006 (8)	0.0004 (8)
C1	0.0188 (11)	0.0145 (11)	0.0168 (10)	0.0014 (9)	0.0030 (8)	0.0013 (9)
C2	0.0211 (12)	0.0231 (13)	0.0217 (11)	−0.0010 (10)	−0.0015 (9)	0.0009 (10)
C3	0.0214 (12)	0.0285 (14)	0.0216 (11)	0.0053 (11)	−0.0002 (9)	0.0035 (10)
C4	0.0250 (13)	0.0195 (13)	0.0263 (12)	0.0072 (10)	0.0063 (10)	0.0062 (10)
C5	0.0268 (13)	0.0155 (12)	0.0242 (11)	0.0022 (10)	0.0021 (9)	−0.0002 (9)
C6	0.0224 (12)	0.0167 (12)	0.0163 (10)	−0.0011 (10)	0.0033 (8)	−0.0007 (9)
C7	0.0249 (12)	0.0162 (12)	0.0225 (11)	−0.0009 (10)	−0.0031 (9)	−0.0013 (9)
C8	0.0206 (11)	0.0176 (12)	0.0214 (10)	−0.0014 (10)	−0.0007 (9)	−0.0009 (9)
C9	0.0210 (12)	0.0139 (11)	0.0183 (10)	0.0005 (9)	−0.0003 (9)	0.0011 (9)
C10	0.0189 (11)	0.0125 (11)	0.0202 (10)	−0.0009 (9)	0.0020 (9)	0.0005 (9)
C11	0.0167 (11)	0.0112 (11)	0.0216 (10)	0.0006 (9)	0.0008 (8)	0.0029 (9)
C12	0.0158 (11)	0.0172 (12)	0.0186 (10)	0.0023 (9)	−0.0014 (8)	0.0024 (9)
C13	0.0200 (11)	0.0110 (11)	0.0217 (10)	−0.0016 (9)	0.0009 (9)	0.0002 (9)
C14	0.0229 (12)	0.0108 (11)	0.0196 (10)	0.0013 (9)	0.0030 (9)	0.0018 (9)
C15	0.0369 (14)	0.0125 (12)	0.0295 (12)	−0.0012 (11)	−0.0089 (11)	0.0023 (10)
C16	0.0241 (12)	0.0163 (12)	0.0276 (12)	0.0004 (10)	−0.0049 (10)	0.0060 (10)
C17	0.0277 (13)	0.0115 (11)	0.0342 (13)	−0.0015 (10)	−0.0051 (10)	0.0025 (10)

Geometric parameters (Å, º) top

O1—C6	1.226 (3)	C7—H7A	0.9300
O2—C10	1.366 (3)	C8—C9	1.468 (3)
O2—C15	1.427 (3)	C8—H8A	0.9300
O3—C12	1.365 (3)	C9—C10	1.400 (3)
O3—C16	1.438 (3)	C9—C14	1.413 (3)
O4—C13	1.366 (3)	C10—C11	1.400 (3)
O4—C17	1.427 (3)	C11—C12	1.378 (3)
N1—C5	1.339 (3)	C11—H11A	0.9300
N1—C1	1.343 (3)	C12—C13	1.412 (3)
C1—C2	1.397 (3)	C13—C14	1.377 (3)
C1—C6	1.511 (3)	C14—H14A	0.9300
C2—C3	1.388 (4)	C15—H15A	0.9600
C2—H2A	0.9300	C15—H15B	0.9600
C3—C4	1.379 (4)	C15—H15C	0.9600
C3—H3A	0.9300	C16—H16A	0.9600
C4—C5	1.392 (3)	C16—H16B	0.9600
C4—H4A	0.9300	C16—H16C	0.9600
C5—H5A	0.9300	C17—H17A	0.9600
C6—C7	1.466 (3)	C17—H17B	0.9600
C7—C8	1.343 (3)	C17—H17C	0.9600

C10—O2—C15	117.81 (18)	O2—C10—C9	115.8 (2)
C12—O3—C16	117.48 (18)	C11—C10—C9	121.0 (2)
C13—O4—C17	117.05 (18)	C12—C11—C10	120.0 (2)
C5—N1—C1	117.3 (2)	C12—C11—H11A	120.0
N1—C1—C2	123.0 (2)	C10—C11—H11A	120.0
N1—C1—C6	117.17 (19)	O3—C12—C11	124.8 (2)
C2—C1—C6	119.9 (2)	O3—C12—C13	114.8 (2)
C3—C2—C1	118.6 (2)	C11—C12—C13	120.3 (2)
C3—C2—H2A	120.7	O4—C13—C14	125.5 (2)
C1—C2—H2A	120.7	O4—C13—C12	115.46 (19)
C4—C3—C2	118.9 (2)	C14—C13—C12	119.0 (2)
C4—C3—H3A	120.6	C13—C14—C9	122.0 (2)
C2—C3—H3A	120.6	C13—C14—H14A	119.0
C3—C4—C5	118.7 (2)	C9—C14—H14A	119.0
C3—C4—H4A	120.6	O2—C15—H15A	109.5
C5—C4—H4A	120.6	O2—C15—H15B	109.5
N1—C5—C4	123.5 (2)	H15A—C15—H15B	109.5
N1—C5—H5A	118.3	O2—C15—H15C	109.5
C4—C5—H5A	118.3	H15A—C15—H15C	109.5
O1—C6—C7	123.3 (2)	H15B—C15—H15C	109.5
O1—C6—C1	120.1 (2)	O3—C16—H16A	109.5
C7—C6—C1	116.6 (2)	O3—C16—H16B	109.5
C8—C7—C6	121.2 (2)	H16A—C16—H16B	109.5
C8—C7—H7A	119.4	O3—C16—H16C	109.5
C6—C7—H7A	119.4	H16A—C16—H16C	109.5
C7—C8—C9	126.9 (2)	H16B—C16—H16C	109.5
C7—C8—H8A	116.6	O4—C17—H17A	109.5
C9—C8—H8A	116.6	O4—C17—H17B	109.5
C10—C9—C14	117.6 (2)	H17A—C17—H17B	109.5
C10—C9—C8	120.0 (2)	O4—C17—H17C	109.5
C14—C9—C8	122.5 (2)	H17A—C17—H17C	109.5
O2—C10—C11	123.1 (2)	H17B—C17—H17C	109.5

C5—N1—C1—C2	0.3 (3)	C8—C9—C10—O2	0.9 (3)
C5—N1—C1—C6	−180.0 (2)	C14—C9—C10—C11	2.1 (3)
N1—C1—C2—C3	−0.8 (3)	C8—C9—C10—C11	−178.7 (2)
C6—C1—C2—C3	179.5 (2)	O2—C10—C11—C12	178.1 (2)
C1—C2—C3—C4	1.0 (3)	C9—C10—C11—C12	−2.4 (3)
C2—C3—C4—C5	−0.7 (3)	C16—O3—C12—C11	−2.8 (3)
C1—N1—C5—C4	0.0 (3)	C16—O3—C12—C13	177.9 (2)
C3—C4—C5—N1	0.2 (4)	C10—C11—C12—O3	−178.3 (2)
N1—C1—C6—O1	−177.7 (2)	C10—C11—C12—C13	1.0 (3)
C2—C1—C6—O1	2.0 (3)	C17—O4—C13—C14	−2.6 (3)
N1—C1—C6—C7	2.9 (3)	C17—O4—C13—C12	176.7 (2)
C2—C1—C6—C7	−177.4 (2)	O3—C12—C13—O4	0.7 (3)
O1—C6—C7—C8	−1.3 (4)	C11—C12—C13—O4	−178.7 (2)
C1—C6—C7—C8	178.0 (2)	O3—C12—C13—C14	−180.0 (2)
C6—C7—C8—C9	179.4 (2)	C11—C12—C13—C14	0.6 (3)
C7—C8—C9—C10	178.8 (2)	O4—C13—C14—C9	178.4 (2)
C7—C8—C9—C14	−2.0 (4)	C12—C13—C14—C9	−0.9 (3)
C15—O2—C10—C11	0.4 (3)	C10—C9—C14—C13	−0.4 (3)
C15—O2—C10—C9	−179.1 (2)	C8—C9—C14—C13	−179.7 (2)
C14—C9—C10—O2	−178.38 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O4ⁱ	0.93	2.39	3.277 (3)	160
C15—H15A···N1ⁱⁱ	0.96	2.47	3.349 (3)	153

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇NO₄
M_r	299.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	8.4047 (3), 8.7285 (3), 19.5086 (7)
β (°)	94.113 (2)
V (Å³)	1427.47 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.32 × 0.27 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.969, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	14970, 3792, 2435
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.188, 1.07
No. of reflections	3792
No. of parameters	202
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.29

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009), Mercury (Macrae et al., 2006) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O4ⁱ	0.93	2.39	3.277 (3)	160
C15—H15A···N1ⁱⁱ	0.96	2.47	3.349 (3)	153

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

Footnotes

‡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 through the Royal Golden Jubilee PhD Program (grant No. PHD/0257/2553) is gratefully acknowledged. The authors extend their appreciation to Prince of Songkla University, the Deanship of Scientific Research at the King Saud University and Universiti Sains Malaysia for the APEX DE2012 grant No.1002/PFIZIK/910323.

References

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