(E)-3-(4-Methyl­phen­yl)-1-(4-nitro­phenyl)prop-2-en-1-one

Fun, H.-K.; Chantrapromma, S.; Patil, P.S.; D'Silva, E.D.; Dharmaprakash, S.M.

doi:10.1107/S1600536808012257

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages o954-o955

doi:10.1107/S1600536808012257

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(E)-3-(4-Methylphenyl)-1-(4-nitrophenyl)prop-2-en-1-one

Hoong-Kun Fun,^a ^* Suchada Chantrapromma,^b ‡ P. S. Patil,^c E. Deepak D'Silva ^c and S. M. Dharmaprakash ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 21 April 2008; accepted 28 April 2008; online 3 May 2008)

The asymmetric unit of the title compound, C₁₆H₁₃NO₃, contains two independent molecules related approximately by a pseudo-twofold rotation axis. The dihedral angle between the nitrobenzene and methylphenyl rings is 42.18 (6)° in one molecule and 12.97 (6)° in the other. In both molecules, the nitro group is slightly twisted away from the attached benzene ring. In the crystal structure, the molecules are stacked along the b axis and are linked via C—H⋯O and C—H⋯π interactions.

Related literature

For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For related structures, see: Fun et al. (2007 ); Patil et al. (2007 a ,b); Patil, Dharmaprakash et al. (2007). For background to the applications of substituted chalcones, see: Agrinskaya et al. (1999 ); Gu et al. (2008 ); Patil et al. (2006 ); Patil, Dharmaprakash et al. (2007).

Experimental

Crystal data

C₁₆H₁₃NO₃
M_r = 267.27
Triclinic, $[P \overline 1]$
a = 5.8857 (1) Å
b = 7.8800 (1) Å
c = 27.4745 (4) Å
α = 88.793 (1)°
β = 85.665 (1)°
γ = 82.645 (1)°
V = 1260.07 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100.0 (1) K
0.43 × 0.26 × 0.23 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.959, T_max = 0.977
32268 measured reflections
6666 independent reflections
5182 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.131
S = 1.09
6666 reflections
363 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1A—H1A⋯O1Bⁱ	0.93	2.58	3.2597 (17)	131
C9A—H9A⋯O1A	0.93	2.48	2.8045 (17)	101
C9B—H9B⋯O1B	0.93	2.48	2.8112 (17)	101
C1B—H1B⋯Cg1	0.93	2.90	3.4853 (15)	123
C4B—H4B⋯Cg1ⁱⁱ	0.93	2.86	3.4837 (15)	126
C16A—H16C⋯Cg2ⁱⁱⁱ	0.96	2.91	3.7837 (15)	151
Symmetry codes: (i) x+1, y-1, z; (ii) x-1, y+1, z; (iii) x+1, y, z. Cg1 and Cg2 are centroids of the C10A–C15A and C1B–C6B rings, ,respectively.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012257/ci2586sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808012257/ci2586Isup2.hkl

checkCIF report

Comment top

Substituted chalcones exhibit second-harmonic generation in crystalline form and possess optical limiting behavior with femtosecond laser pulse at 780 nm wavelength (Gu et al., 2008; Patil et al., 2006, 2007c; Agrinskaya et al., 1999). The main idea behind the above studies was to introduce various donor/acceptor substituents [OCH₃, N(CH₃)₂, NH₂, F, Cl, Br, CH₃, NO₂] on either side of benzene rings and to observe the structure-activity relationship. In view of the importance of substituted chalcones, the title compound was synthesized and its crystal structure is reported here.

There are two independent molecules, A and B, in the asymmetric unit of the title compound (Fig. 1). Bond lengths and angles in both molecules are in normal ranges (Allen et al., 1987) and comparable to those in related structures (Fun et al., 2007; Patil et al., 2007a,b). The dihedral angles between the nitrobenzene and methylphenyl rings are 42.18 (6)° and 12.97 (6)° in molecule A and B, respectively. In molecule A, atoms O1A, C6A, C7A and C8A are coplanar and the least-squares plane through these atoms makes dihedral angles of 20.21 (8)° and 24.41 (7)° with the nitrobenzene (C1A–C6A) and methylbenzene (C10A–C15A) rings, repectively. However, in molecule B atoms O1B, C6B, C7B, C8B, C9B and C10B are coplanar, and the dihedral angles formed by the mean plane through these atoms with the nirobenzene and methylbenzene rings are 16.85 (6)° and 16.97 (6)°, respectively. The nitro groups are slightly twisted away from the plane of the attached benzene rings, with the O2—N1—C3—C2 torsion angles being 11.2 (2)° and 5.84 (19)° in molecules A and B, respectively, and the O3—N1—C3—C4 torsion angles being 11.5 (2)° and 4.54 (19)°, in A and B,respectively. In each of the independent molecules, a weak C9—H9···O1 interaction generates an S(5) ring motif (Bernstein et al., 1995) (Table 1).

In the crystal structure (Fig. 2), the molecules are stacked in as anti-parallel pairs approximately along the b axis. The crystal structure is stabilized by weak C—H···O hydrogen bonds and C—H···π interactions (Table 1) involving the C10A-C15A (centroid Cg1) and C1B-C6B (centroid Cg2) benzene rings.

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: Fun et al. (2007); Patil et al. (2007a,b); Patil, Dharmaprakash et al. (2007). For background to the applications of substituted chalcones, see: Agrinskaya et al. (1999); Gu et al. (2008); Patil et al. (2006); Patil, Dharmaprakash et al. (2007). Cg1 and Cg2 are centroids of the C10A–C15A and C1B–C6B rings,respectively.

Experimental top

The title compound was synthesized by the condensation of p-tolualdehyde (0.01 mol) with 4-nitroacetophenone (0.01 mol) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (5 ml, 30%). After stirring for 2 hr, the contents of the flask were poured into ice-cold water (500 ml) and left to stand for 5 hr. The resulting crude solid was filtered and dried. Yellow single crystals of the title compound suitable for X-ray structure determination were recrystallized from N,N-dimethylformamide (DMF).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (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, 2003).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering. Weak C—H···O intramolecular interactions are drawn as dashed lines.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis showing stacking of anti-parallel pairs of molecules approximately along the b axis. Hydrogen bonds are drawn as dashed lines.

3-(4-methylphenyl)-1-(4-nitrophenyl)prop-2-en-1-one top

Crystal data top

C₁₆H₁₃NO₃	Z = 4
M_r = 267.27	F(000) = 560
Triclinic, P1	D_x = 1.409 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8857 (1) Å	Cell parameters from 6666 reflections
b = 7.8800 (1) Å	θ = 0.7–29.0°
c = 27.4745 (4) Å	µ = 0.10 mm⁻¹
α = 88.793 (1)°	T = 100 K
β = 85.665 (1)°	Block, yellow
γ = 82.645 (1)°	0.43 × 0.26 × 0.23 mm
V = 1260.07 (3) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6666 independent reflections
Radiation source: fine-focus sealed tube	5182 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 8.33 pixels mm^-1	θ_max = 29.0°, θ_min = 0.7°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→8
T_min = 0.959, T_max = 0.977	l = −37→37
32268 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.061P)² + 0.3735P] where P = (F_o² + 2F_c²)/3
6666 reflections	(Δ/σ)_max = 0.001
363 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₆H₁₃NO₃	γ = 82.645 (1)°
M_r = 267.27	V = 1260.07 (3) Å³
Triclinic, P1	Z = 4
a = 5.8857 (1) Å	Mo Kα radiation
b = 7.8800 (1) Å	µ = 0.10 mm⁻¹
c = 27.4745 (4) Å	T = 100 K
α = 88.793 (1)°	0.43 × 0.26 × 0.23 mm
β = 85.665 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6666 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	5182 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.977	R_int = 0.033
32268 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.09	Δρ_max = 0.38 e Å⁻³
6666 reflections	Δρ_min = −0.26 e Å⁻³
363 parameters

Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
O1A	0.21638 (17)	0.20887 (14)	0.77198 (4)	0.0239 (2)
O2A	0.88278 (19)	−0.18446 (17)	0.96280 (4)	0.0382 (3)
O3A	0.52447 (19)	−0.18264 (14)	0.98705 (4)	0.0271 (2)
N1A	0.6782 (2)	−0.14787 (16)	0.95730 (4)	0.0219 (3)
C1A	0.7223 (2)	0.03671 (18)	0.83164 (5)	0.0193 (3)
H1A	0.8340	0.0463	0.8063	0.023*
C2A	0.7813 (2)	−0.04744 (18)	0.87474 (5)	0.0196 (3)
H2A	0.9319	−0.0955	0.8785	0.024*
C3A	0.6122 (2)	−0.05826 (17)	0.91193 (5)	0.0171 (3)
C4A	0.3867 (2)	0.00997 (18)	0.90810 (5)	0.0203 (3)
H4A	0.2761	0.0009	0.9337	0.024*
C5A	0.3298 (2)	0.09255 (18)	0.86483 (5)	0.0197 (3)
H5A	0.1786	0.1394	0.8613	0.024*
C6A	0.4958 (2)	0.10657 (17)	0.82647 (5)	0.0158 (3)
C7A	0.4201 (2)	0.19297 (17)	0.77999 (5)	0.0169 (3)
C8A	0.5949 (2)	0.25902 (17)	0.74603 (5)	0.0174 (3)
H8A	0.7450	0.2555	0.7548	0.021*
C9A	0.5374 (2)	0.32427 (17)	0.70247 (5)	0.0170 (3)
H9A	0.3891	0.3156	0.6941	0.020*
C10A	0.6854 (2)	0.40782 (17)	0.66680 (5)	0.0158 (3)
C11A	0.6179 (2)	0.43784 (17)	0.61919 (5)	0.0172 (3)
H11A	0.4811	0.4026	0.6109	0.021*
C12A	0.7501 (2)	0.51888 (17)	0.58421 (5)	0.0185 (3)
H12A	0.7027	0.5350	0.5527	0.022*
C13A	0.9536 (2)	0.57638 (17)	0.59585 (5)	0.0179 (3)
C14A	1.0189 (2)	0.54932 (17)	0.64355 (5)	0.0181 (3)
H14A	1.1525	0.5887	0.6521	0.022*
C15A	0.8900 (2)	0.46549 (17)	0.67837 (5)	0.0177 (3)
H15A	0.9396	0.4474	0.7096	0.021*
C16A	1.0971 (2)	0.66602 (19)	0.55834 (5)	0.0224 (3)
H16A	0.9997	0.7509	0.5414	0.034*
H16B	1.1753	0.5841	0.5354	0.034*
H16C	1.2079	0.7203	0.5743	0.034*
O1B	−0.02096 (17)	0.84372 (13)	0.73497 (4)	0.0228 (2)
O2B	0.65858 (19)	1.10645 (15)	0.52474 (4)	0.0302 (3)
O3B	0.3249 (2)	1.25845 (15)	0.52514 (4)	0.0342 (3)
N1B	0.4637 (2)	1.14949 (16)	0.54285 (4)	0.0227 (3)
C1B	0.4905 (2)	0.88516 (18)	0.65652 (5)	0.0193 (3)
H1B	0.5979	0.8123	0.6726	0.023*
C2B	0.5542 (2)	0.95813 (18)	0.61183 (5)	0.0196 (3)
H2B	0.7030	0.9339	0.5976	0.024*
C3B	0.3911 (2)	1.06743 (17)	0.58920 (5)	0.0181 (3)
C4B	0.1681 (2)	1.10666 (18)	0.60879 (5)	0.0204 (3)
H4B	0.0625	1.1817	0.5928	0.024*
C5B	0.1060 (2)	1.03113 (18)	0.65291 (5)	0.0192 (3)
H5B	−0.0441	1.0541	0.6665	0.023*
C6B	0.2662 (2)	0.92085 (17)	0.67722 (5)	0.0167 (3)
C7B	0.1851 (2)	0.84063 (17)	0.72448 (5)	0.0175 (3)
C8B	0.3587 (2)	0.75994 (18)	0.75670 (5)	0.0190 (3)
H8B	0.5139	0.7541	0.7466	0.023*
C9B	0.2950 (2)	0.69516 (17)	0.80024 (5)	0.0186 (3)
H9B	0.1380	0.7050	0.8089	0.022*
C10B	0.4455 (2)	0.61059 (17)	0.83569 (5)	0.0176 (3)
C11B	0.3559 (2)	0.57945 (18)	0.88324 (5)	0.0196 (3)
H11B	0.2014	0.6141	0.8919	0.024*
C12B	0.4946 (2)	0.49752 (18)	0.91766 (5)	0.0203 (3)
H12B	0.4320	0.4792	0.9491	0.024*
C13B	0.7260 (2)	0.44249 (18)	0.90559 (5)	0.0194 (3)
C14B	0.8147 (2)	0.47184 (18)	0.85790 (5)	0.0197 (3)
H14B	0.9684	0.4348	0.8490	0.024*
C15B	0.6776 (2)	0.55527 (18)	0.82360 (5)	0.0192 (3)
H15B	0.7408	0.5746	0.7922	0.023*
C16B	0.8747 (3)	0.3557 (2)	0.94323 (5)	0.0236 (3)
H16D	0.8475	0.4184	0.9731	0.035*
H16E	1.0334	0.3520	0.9317	0.035*
H16F	0.8385	0.2413	0.9489	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0172 (5)	0.0334 (6)	0.0213 (5)	−0.0041 (4)	−0.0029 (4)	0.0080 (4)
O2A	0.0253 (6)	0.0570 (8)	0.0311 (6)	0.0002 (5)	−0.0093 (5)	0.0183 (6)
O3A	0.0333 (6)	0.0294 (6)	0.0187 (5)	−0.0066 (5)	0.0006 (4)	0.0073 (4)
N1A	0.0267 (6)	0.0219 (6)	0.0173 (6)	−0.0033 (5)	−0.0037 (5)	0.0040 (5)
C1A	0.0173 (6)	0.0225 (7)	0.0174 (6)	−0.0017 (5)	0.0016 (5)	0.0022 (5)
C2A	0.0172 (6)	0.0226 (7)	0.0187 (7)	−0.0005 (5)	−0.0023 (5)	0.0035 (5)
C3A	0.0205 (7)	0.0170 (6)	0.0143 (6)	−0.0036 (5)	−0.0030 (5)	0.0023 (5)
C4A	0.0190 (7)	0.0243 (7)	0.0175 (6)	−0.0040 (5)	0.0014 (5)	0.0032 (5)
C5A	0.0165 (6)	0.0232 (7)	0.0187 (6)	−0.0009 (5)	−0.0009 (5)	0.0037 (5)
C6A	0.0171 (6)	0.0146 (6)	0.0161 (6)	−0.0034 (5)	−0.0014 (5)	0.0010 (5)
C7A	0.0186 (6)	0.0172 (6)	0.0147 (6)	−0.0024 (5)	−0.0002 (5)	0.0017 (5)
C8A	0.0159 (6)	0.0177 (6)	0.0184 (6)	−0.0025 (5)	0.0000 (5)	0.0012 (5)
C9A	0.0159 (6)	0.0181 (6)	0.0166 (6)	−0.0015 (5)	−0.0002 (5)	0.0005 (5)
C10A	0.0166 (6)	0.0146 (6)	0.0155 (6)	−0.0002 (5)	0.0001 (5)	0.0012 (5)
C11A	0.0163 (6)	0.0178 (6)	0.0176 (6)	−0.0027 (5)	−0.0010 (5)	−0.0002 (5)
C12A	0.0223 (7)	0.0190 (7)	0.0132 (6)	−0.0001 (5)	−0.0004 (5)	0.0014 (5)
C13A	0.0190 (6)	0.0149 (6)	0.0184 (6)	0.0005 (5)	0.0028 (5)	0.0013 (5)
C14A	0.0150 (6)	0.0189 (7)	0.0204 (7)	−0.0028 (5)	−0.0001 (5)	−0.0006 (5)
C15A	0.0185 (6)	0.0187 (7)	0.0155 (6)	−0.0010 (5)	−0.0011 (5)	0.0005 (5)
C16A	0.0235 (7)	0.0222 (7)	0.0208 (7)	−0.0040 (6)	0.0038 (5)	0.0027 (5)
O1B	0.0193 (5)	0.0286 (6)	0.0201 (5)	−0.0027 (4)	−0.0007 (4)	0.0026 (4)
O2B	0.0307 (6)	0.0363 (6)	0.0235 (5)	−0.0083 (5)	0.0044 (4)	0.0055 (5)
O3B	0.0455 (7)	0.0300 (6)	0.0249 (6)	0.0027 (5)	−0.0036 (5)	0.0107 (5)
N1B	0.0318 (7)	0.0202 (6)	0.0169 (6)	−0.0065 (5)	−0.0013 (5)	0.0020 (5)
C1B	0.0185 (6)	0.0180 (7)	0.0209 (7)	−0.0001 (5)	−0.0033 (5)	0.0033 (5)
C2B	0.0173 (6)	0.0197 (7)	0.0212 (7)	−0.0014 (5)	0.0009 (5)	−0.0002 (5)
C3B	0.0255 (7)	0.0152 (6)	0.0140 (6)	−0.0045 (5)	−0.0020 (5)	0.0012 (5)
C4B	0.0227 (7)	0.0179 (7)	0.0201 (7)	0.0006 (5)	−0.0052 (5)	0.0019 (5)
C5B	0.0181 (6)	0.0191 (7)	0.0199 (7)	−0.0002 (5)	−0.0016 (5)	0.0002 (5)
C6B	0.0187 (6)	0.0160 (6)	0.0156 (6)	−0.0029 (5)	−0.0022 (5)	0.0001 (5)
C7B	0.0191 (6)	0.0163 (6)	0.0170 (6)	−0.0021 (5)	−0.0015 (5)	−0.0004 (5)
C8B	0.0176 (6)	0.0206 (7)	0.0187 (7)	−0.0014 (5)	−0.0022 (5)	0.0017 (5)
C9B	0.0193 (6)	0.0181 (7)	0.0184 (6)	−0.0020 (5)	−0.0016 (5)	0.0008 (5)
C10B	0.0204 (7)	0.0177 (6)	0.0155 (6)	−0.0047 (5)	−0.0028 (5)	0.0018 (5)
C11B	0.0181 (6)	0.0225 (7)	0.0179 (6)	−0.0024 (5)	−0.0003 (5)	0.0024 (5)
C12B	0.0234 (7)	0.0222 (7)	0.0152 (6)	−0.0036 (6)	−0.0010 (5)	0.0035 (5)
C13B	0.0215 (7)	0.0175 (7)	0.0198 (7)	−0.0043 (5)	−0.0032 (5)	0.0011 (5)
C14B	0.0179 (6)	0.0214 (7)	0.0194 (7)	−0.0015 (5)	−0.0012 (5)	0.0018 (5)
C15B	0.0226 (7)	0.0200 (7)	0.0150 (6)	−0.0040 (5)	−0.0001 (5)	0.0012 (5)
C16B	0.0237 (7)	0.0290 (8)	0.0177 (7)	−0.0020 (6)	−0.0027 (5)	0.0057 (6)

Geometric parameters (Å, º) top

O1A—C7A	1.2256 (16)	O1B—C7B	1.2224 (17)
O2A—N1A	1.2219 (16)	O2B—N1B	1.2245 (16)
O3A—N1A	1.2263 (16)	O3B—N1B	1.2264 (16)
N1A—C3A	1.4728 (17)	N1B—C3B	1.4751 (17)
C1A—C2A	1.3903 (18)	C1B—C2B	1.3909 (19)
C1A—C6A	1.3919 (18)	C1B—C6B	1.3944 (19)
C1A—H1A	0.93	C1B—H1B	0.93
C2A—C3A	1.3805 (19)	C2B—C3B	1.3808 (19)
C2A—H2A	0.93	C2B—H2B	0.93
C3A—C4A	1.3780 (19)	C3B—C4B	1.380 (2)
C4A—C5A	1.3857 (18)	C4B—C5B	1.3839 (19)
C4A—H4A	0.93	C4B—H4B	0.93
C5A—C6A	1.3944 (18)	C5B—C6B	1.3969 (18)
C5A—H5A	0.93	C5B—H5B	0.93
C6A—C7A	1.5048 (18)	C6B—C7B	1.5039 (18)
C7A—C8A	1.4735 (18)	C7B—C8B	1.4759 (18)
C8A—C9A	1.3422 (18)	C8B—C9B	1.3370 (19)
C8A—H8A	0.93	C8B—H8B	0.93
C9A—C10A	1.4644 (18)	C9B—C10B	1.4594 (18)
C9A—H9A	0.93	C9B—H9B	0.93
C10A—C15A	1.4002 (19)	C10B—C15B	1.3966 (19)
C10A—C11A	1.4024 (18)	C10B—C11B	1.4002 (18)
C11A—C12A	1.3876 (18)	C11B—C12B	1.3903 (18)
C11A—H11A	0.93	C11B—H11B	0.93
C12A—C13A	1.395 (2)	C12B—C13B	1.393 (2)
C12A—H12A	0.93	C12B—H12B	0.93
C13A—C14A	1.3976 (19)	C13B—C14B	1.3992 (19)
C13A—C16A	1.5050 (18)	C13B—C16B	1.5024 (19)
C14A—C15A	1.3853 (18)	C14B—C15B	1.3874 (19)
C14A—H14A	0.93	C14B—H14B	0.93
C15A—H15A	0.93	C15B—H15B	0.93
C16A—H16A	0.96	C16B—H16D	0.96
C16A—H16B	0.96	C16B—H16E	0.96
C16A—H16C	0.96	C16B—H16F	0.96

O2A—N1A—O3A	123.99 (12)	O2B—N1B—O3B	124.08 (12)
O2A—N1A—C3A	117.98 (12)	O2B—N1B—C3B	118.32 (12)
O3A—N1A—C3A	118.03 (12)	O3B—N1B—C3B	117.60 (12)
C2A—C1A—C6A	119.95 (12)	C2B—C1B—C6B	120.27 (12)
C2A—C1A—H1A	120.0	C2B—C1B—H1B	119.9
C6A—C1A—H1A	120.0	C6B—C1B—H1B	119.9
C3A—C2A—C1A	118.73 (12)	C3B—C2B—C1B	118.31 (13)
C3A—C2A—H2A	120.6	C3B—C2B—H2B	120.8
C1A—C2A—H2A	120.6	C1B—C2B—H2B	120.8
C4A—C3A—C2A	122.82 (12)	C4B—C3B—C2B	122.99 (12)
C4A—C3A—N1A	119.25 (12)	C4B—C3B—N1B	119.29 (12)
C2A—C3A—N1A	117.92 (12)	C2B—C3B—N1B	117.69 (12)
C3A—C4A—C5A	117.86 (12)	C3B—C4B—C5B	118.12 (12)
C3A—C4A—H4A	121.1	C3B—C4B—H4B	120.9
C5A—C4A—H4A	121.1	C5B—C4B—H4B	120.9
C4A—C5A—C6A	121.03 (13)	C4B—C5B—C6B	120.75 (13)
C4A—C5A—H5A	119.5	C4B—C5B—H5B	119.6
C6A—C5A—H5A	119.5	C6B—C5B—H5B	119.6
C1A—C6A—C5A	119.60 (12)	C1B—C6B—C5B	119.56 (12)
C1A—C6A—C7A	122.29 (12)	C1B—C6B—C7B	122.63 (12)
C5A—C6A—C7A	118.08 (12)	C5B—C6B—C7B	117.79 (12)
O1A—C7A—C8A	122.24 (12)	O1B—C7B—C8B	122.13 (12)
O1A—C7A—C6A	119.41 (12)	O1B—C7B—C6B	119.37 (12)
C8A—C7A—C6A	118.34 (11)	C8B—C7B—C6B	118.50 (12)
C9A—C8A—C7A	120.01 (12)	C9B—C8B—C7B	120.66 (13)
C9A—C8A—H8A	120.0	C9B—C8B—H8B	119.7
C7A—C8A—H8A	120.0	C7B—C8B—H8B	119.7
C8A—C9A—C10A	126.33 (13)	C8B—C9B—C10B	126.94 (13)
C8A—C9A—H9A	116.8	C8B—C9B—H9B	116.5
C10A—C9A—H9A	116.8	C10B—C9B—H9B	116.5
C15A—C10A—C11A	117.72 (12)	C15B—C10B—C11B	118.17 (12)
C15A—C10A—C9A	122.96 (12)	C15B—C10B—C9B	122.17 (12)
C11A—C10A—C9A	119.28 (12)	C11B—C10B—C9B	119.65 (12)
C12A—C11A—C10A	121.57 (13)	C12B—C11B—C10B	120.96 (13)
C12A—C11A—H11A	119.2	C12B—C11B—H11B	119.5
C10A—C11A—H11A	119.2	C10B—C11B—H11B	119.5
C11A—C12A—C13A	120.58 (12)	C11B—C12B—C13B	120.84 (13)
C11A—C12A—H12A	119.7	C11B—C12B—H12B	119.6
C13A—C12A—H12A	119.7	C13B—C12B—H12B	119.6
C12A—C13A—C14A	117.86 (12)	C12B—C13B—C14B	118.14 (12)
C12A—C13A—C16A	121.01 (12)	C12B—C13B—C16B	120.38 (12)
C14A—C13A—C16A	121.13 (13)	C14B—C13B—C16B	121.47 (13)
C15A—C14A—C13A	121.84 (13)	C15B—C14B—C13B	121.19 (13)
C15A—C14A—H14A	119.1	C15B—C14B—H14B	119.4
C13A—C14A—H14A	119.1	C13B—C14B—H14B	119.4
C14A—C15A—C10A	120.40 (12)	C14B—C15B—C10B	120.68 (12)
C14A—C15A—H15A	119.8	C14B—C15B—H15B	119.7
C10A—C15A—H15A	119.8	C10B—C15B—H15B	119.7
C13A—C16A—H16A	109.5	C13B—C16B—H16D	109.5
C13A—C16A—H16B	109.5	C13B—C16B—H16E	109.5
H16A—C16A—H16B	109.5	H16D—C16B—H16E	109.5
C13A—C16A—H16C	109.5	C13B—C16B—H16F	109.5
H16A—C16A—H16C	109.5	H16D—C16B—H16F	109.5
H16B—C16A—H16C	109.5	H16E—C16B—H16F	109.5

C6A—C1A—C2A—C3A	−0.6 (2)	C6B—C1B—C2B—C3B	0.8 (2)
C1A—C2A—C3A—C4A	0.4 (2)	C1B—C2B—C3B—C4B	−0.3 (2)
C1A—C2A—C3A—N1A	−179.99 (13)	C1B—C2B—C3B—N1B	177.49 (12)
O2A—N1A—C3A—C4A	−169.19 (14)	O2B—N1B—C3B—C4B	−176.27 (13)
O3A—N1A—C3A—C4A	11.5 (2)	O3B—N1B—C3B—C4B	4.54 (19)
O2A—N1A—C3A—C2A	11.2 (2)	O2B—N1B—C3B—C2B	5.84 (19)
O3A—N1A—C3A—C2A	−168.15 (13)	O3B—N1B—C3B—C2B	−173.35 (13)
C2A—C3A—C4A—C5A	0.0 (2)	C2B—C3B—C4B—C5B	−0.7 (2)
N1A—C3A—C4A—C5A	−179.61 (13)	N1B—C3B—C4B—C5B	−178.43 (12)
C3A—C4A—C5A—C6A	−0.2 (2)	C3B—C4B—C5B—C6B	1.2 (2)
C2A—C1A—C6A—C5A	0.5 (2)	C2B—C1B—C6B—C5B	−0.3 (2)
C2A—C1A—C6A—C7A	−177.56 (13)	C2B—C1B—C6B—C7B	177.65 (13)
C4A—C5A—C6A—C1A	0.0 (2)	C4B—C5B—C6B—C1B	−0.7 (2)
C4A—C5A—C6A—C7A	178.06 (13)	C4B—C5B—C6B—C7B	−178.75 (13)
C1A—C6A—C7A—O1A	159.57 (14)	C1B—C6B—C7B—O1B	−162.74 (14)
C5A—C6A—C7A—O1A	−18.5 (2)	C5B—C6B—C7B—O1B	15.3 (2)
C1A—C6A—C7A—C8A	−21.7 (2)	C1B—C6B—C7B—C8B	17.1 (2)
C5A—C6A—C7A—C8A	160.26 (13)	C5B—C6B—C7B—C8B	−164.91 (12)
O1A—C7A—C8A—C9A	−6.7 (2)	O1B—C7B—C8B—C9B	−3.8 (2)
C6A—C7A—C8A—C9A	174.58 (12)	C6B—C7B—C8B—C9B	176.38 (13)
C7A—C8A—C9A—C10A	174.30 (12)	C7B—C8B—C9B—C10B	179.38 (13)
C8A—C9A—C10A—C15A	−15.3 (2)	C8B—C9B—C10B—C15B	−13.8 (2)
C8A—C9A—C10A—C11A	167.03 (13)	C8B—C9B—C10B—C11B	167.69 (14)
C15A—C10A—C11A—C12A	1.2 (2)	C15B—C10B—C11B—C12B	0.7 (2)
C9A—C10A—C11A—C12A	179.00 (12)	C9B—C10B—C11B—C12B	179.31 (13)
C10A—C11A—C12A—C13A	−1.3 (2)	C10B—C11B—C12B—C13B	−0.7 (2)
C11A—C12A—C13A—C14A	0.1 (2)	C11B—C12B—C13B—C14B	−0.1 (2)
C11A—C12A—C13A—C16A	−179.37 (13)	C11B—C12B—C13B—C16B	179.37 (14)
C12A—C13A—C14A—C15A	1.2 (2)	C12B—C13B—C14B—C15B	0.8 (2)
C16A—C13A—C14A—C15A	−179.32 (13)	C16B—C13B—C14B—C15B	−178.62 (14)
C13A—C14A—C15A—C10A	−1.3 (2)	C13B—C14B—C15B—C10B	−0.8 (2)
C11A—C10A—C15A—C14A	0.09 (19)	C11B—C10B—C15B—C14B	0.0 (2)
C9A—C10A—C15A—C14A	−177.62 (12)	C9B—C10B—C15B—C14B	−178.54 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1A—H1A···O1Bⁱ	0.93	2.58	3.2597 (17)	131
C9A—H9A···O1A	0.93	2.48	2.8045 (17)	101
C9B—H9B···O1B	0.93	2.48	2.8112 (17)	101
C1B—H1B···Cg1	0.93	2.90	3.4853 (15)	123
C4B—H4B···Cg1ⁱⁱ	0.93	2.86	3.4837 (15)	126
C16A—H16C···Cg2ⁱⁱⁱ	0.96	2.91	3.7837 (15)	151

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃NO₃
M_r	267.27
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	5.8857 (1), 7.8800 (1), 27.4745 (4)
α, β, γ (°)	88.793 (1), 85.665 (1), 82.645 (1)
V (Å³)	1260.07 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.43 × 0.26 × 0.23

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.959, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	32268, 6666, 5182
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.131, 1.09
No. of reflections	6666
No. of parameters	363
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.26

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1A—H1A···O1Bⁱ	0.93	2.58	3.2597 (17)	131
C9A—H9A···O1A	0.93	2.48	2.8045 (17)	101
C9B—H9B···O1B	0.93	2.48	2.8112 (17)	101
C1B—H1B···Cg1	0.93	2.90	3.4853 (15)	123
C4B—H4B···Cg1ⁱⁱ	0.93	2.86	3.4837 (15)	126
C16A—H16C···Cg2ⁱⁱⁱ	0.96	2.91	3.7837 (15)	151

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

Footnotes

‡Additional correspondence author, e-mail: suchada.c@psu.ac.th.

Acknowledgements

This work is supported by the Department of Science and Technology (DST), Government of India, under grant No. SR/S2/LOP-17/2006. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

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