2-Phenyl-4-(3,4,5-trimethoxy­benzyl­idene)-1,3-oxazol-5(4H)-one

Sun, Y.-F.; Cui, Y.-P.

doi:10.1107/S1600536808005746

organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o678

doi:10.1107/S1600536808005746

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2-Phenyl-4-(3,4,5-trimethoxybenzylidene)-1,3-oxazol-5(4H)-one

Yi-Feng Sun ^a,^b ^* and Yi-Ping Cui ^a

^aAdvanced Photonics Center, School of Electronic Science and Engineering, Southeast University, 210096 Nanjing, Jiangsu, People's Republic of China, and ^bDepartment of Chemistry, Taishan University, 271021 Taian, Shandong, People's Republic of China
^*Correspondence e-mail: sunyf50@hotmail.com

(Received 22 February 2008; accepted 29 February 2008; online 7 March 2008)

The title compound, C₁₉H₁₇NO₅, was synthesized as part of a continuing project involving the structures of oxazolone derivatives. The molecule adopts a Z configuration about the central olefinic bond. The 2-phenyl ring is slightly twisted out of the plane of the oxazolone ring system by 11.2 (2)°. The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For background literature, see: Aaglawe et al. (2003 ); Grassi et al. (2004 ); Khan et al. (2006 ); Song et al. (2001 ). For related structures, see: Sun et al. (2007 ); Imhof & Garms (2005 ); Song et al. (2004 ); Vasuki et al. (2001 ).

Experimental

Crystal data

C₁₉H₁₇NO₅
M_r = 339.34
Triclinic, $[P \overline 1]$
a = 7.3897 (5) Å
b = 8.1532 (6) Å
c = 14.0023 (9) Å
α = 86.917 (5)°
β = 83.306 (4)°
γ = 82.471 (5)°
V = 830.02 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 273 (2) K
0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.985, T_max = 0.990
4665 measured reflections
2904 independent reflections
2056 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.121
S = 1.04
2904 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O1ⁱ	0.93	2.59	3.503 (2)	168
C6—H6⋯O3ⁱⁱ	0.93	2.62	3.420 (2)	144
Symmetry codes: (i) -x+1, -y, -z; (ii) -x, -y+2, -z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005746/pk2085sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808005746/pk2085Isup2.hkl

checkCIF report

Comment top

The development of highly efficient nonlinear optical crystals is extremely important for laser spectroscopy and laser processing. Oxazolone derivatives are highly versatile intermediates used for the synthesis of several biologically active organic molecules, such as amino acids, peptides, antimicrobial or antitumor compounds, immunomodulators, heterocyclic precursors for biosensor coupling, and photosensitive composition devices for proteins (Aaglawe et al., 2003; Grassi et al., 2004; Khan et al., 2006). It has been reported (Song et al., 2001) that some oxazolone derivatives exhibit promising nonlinear optical properties. The second-harmonic generation (SHG) value of the title compound is 1.821, as compared with urea powder. In this contribution, we report the crystal structure of the title compound.

The molecule possesses normal geometric parameters and adopts a Z configuration about the central olefinic bond (Fig. 1). The C11–C16 phenyl ring and the oxazolone ring are almost coplanar. However, the C4–C9 phenyl ring is slightly twisted out of the plane of the oxazolone ring system by 11.2 (2) °. Comparison with 2,6-dimethoxy-4- (5-oxo-2-phenyl-4,5-dihydro-1,3-oxazol-4-ylidenemethyl)-phenyl acetate (Sun et al., 2007) suggests that the presence of the 4-methoxy group leads to this deviation from coplanarity. Also, while O3, O4, O5, C17 and C19 are approximately coplanar with their attached benzene ring, C18 deviate from their mother benzene ring (Fig. 1). The crystal structure is stabilized by the weak intermolecular C—H···O hydrogen bonds (Table 1).

Similar structures have been observed in the related oxazolone analogues reported by Sun et al. (2007), Imhof & Garms (2005), Song et al. (2004), and by Vasuki et al. (2001).

Related literature top

For background literature, see: Aaglawe et al. (2003); Grassi et al. (2004); Khan et al. (2006); Song et al. (2001). For related structures, see: Sun et al. (2007); Imhof & Garms (2005); Song et al. (2004); Vasuki et al. (2001).

Experimental top

The title compound was synthesized from 3,4,5-trimethoxybenzaldehyde and hippuric acid as reported by Song et al. (2001). A mixture of hippuric acid (2.2 mmol), 3,4,5-trimethoxybenzaldehyde (2 mmol), sodium acetate (3 mmol) in acetic anhydride (8 ml) was refluxed for 5 hr. It was then cooled and ethanol (10 ml) was added to it. The resulting mixture was left over night at room temp. The solid thus obtained was filtered, dried and crystallized from ethanol to yield the title compound in 73% yield. A single-crystal suitable for an X-ray structural analysis was obtained by slowly evaporating from ethanol at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of the title molecule showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.

2-Phenyl-4-(3,4,5-trimethoxybenzylidene)-1,3-oxazol-5(4H)-one top

Crystal data top

C₁₉H₁₇NO₅	Z = 2
M_r = 339.34	F(000) = 356
Triclinic, P1	D_x = 1.358 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3897 (5) Å	Cell parameters from 1358 reflections
b = 8.1532 (6) Å	θ = 2.9–24.7°
c = 14.0023 (9) Å	µ = 0.10 mm⁻¹
α = 86.917 (5)°	T = 273 K
β = 83.306 (4)°	Block, yellow
γ = 82.471 (5)°	0.15 × 0.12 × 0.10 mm
V = 830.02 (10) Å³

Data collection top

Bruker SMART CCD area detector diffractometer	2904 independent reflections
Radiation source: fine-focus sealed tube	2056 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 25.1°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.985, T_max = 0.990	k = −9→8
4665 measured reflections	l = −16→14

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: difference Fourier map
wR(F²) = 0.121	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0602P)² + 0.0668P] where P = (F_o² + 2F_c²)/3
2904 reflections	(Δ/σ)_max < 0.001
229 parameters	Δρ_max = 0.12 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₉H₁₇NO₅	γ = 82.471 (5)°
M_r = 339.34	V = 830.02 (10) Å³
Triclinic, P1	Z = 2
a = 7.3897 (5) Å	Mo Kα radiation
b = 8.1532 (6) Å	µ = 0.10 mm⁻¹
c = 14.0023 (9) Å	T = 273 K
α = 86.917 (5)°	0.15 × 0.12 × 0.10 mm
β = 83.306 (4)°

Data collection top

Bruker SMART CCD area detector diffractometer	2904 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2056 reflections with I > 2σ(I)
T_min = 0.985, T_max = 0.990	R_int = 0.020
4665 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.04	Δρ_max = 0.12 e Å⁻³
2904 reflections	Δρ_min = −0.15 e Å⁻³
229 parameters

Special details top

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 > 2σ(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	0.5421 (2)	0.11697 (18)	−0.16116 (10)	0.0843 (5)
O2	0.47613 (18)	0.36419 (17)	−0.23924 (9)	0.0666 (4)
O3	−0.0038 (2)	0.77451 (16)	0.17976 (10)	0.0760 (4)
O4	−0.0466 (2)	0.58784 (18)	0.33970 (10)	0.0759 (4)
O5	0.09472 (19)	0.26856 (16)	0.34793 (9)	0.0685 (4)
N1	0.3293 (2)	0.51906 (19)	−0.11774 (10)	0.0559 (4)
C1	0.4742 (3)	0.2583 (3)	−0.15782 (14)	0.0626 (5)
C2	0.3888 (2)	0.5149 (2)	−0.20767 (13)	0.0560 (5)
C3	0.3759 (2)	0.3591 (2)	−0.07986 (13)	0.0546 (4)
C4	0.3748 (2)	0.6523 (2)	−0.27805 (12)	0.0567 (5)
C5	0.3176 (3)	0.8105 (3)	−0.24711 (14)	0.0656 (5)
H5	0.2910	0.8276	−0.1816	0.079*
C6	0.2996 (3)	0.9427 (3)	−0.31155 (15)	0.0720 (6)
H6	0.2600	1.0486	−0.2898	0.086*
C7	0.3402 (3)	0.9181 (3)	−0.40840 (15)	0.0764 (6)
H7	0.3282	1.0074	−0.4524	0.092*
C8	0.3981 (3)	0.7630 (3)	−0.43997 (15)	0.0836 (7)
H8	0.4258	0.7471	−0.5056	0.100*
C9	0.4161 (3)	0.6292 (3)	−0.37596 (14)	0.0742 (6)
H9	0.4558	0.5237	−0.3983	0.089*
C10	0.3399 (2)	0.2976 (2)	0.01042 (13)	0.0566 (5)
H10	0.3867	0.1873	0.0207	0.068*
C11	0.2390 (2)	0.3772 (2)	0.09430 (12)	0.0509 (4)
C12	0.1654 (2)	0.5438 (2)	0.09198 (13)	0.0551 (4)
H12	0.1786	0.6078	0.0352	0.066*
C13	0.0733 (2)	0.6129 (2)	0.17411 (13)	0.0560 (4)
C14	0.0515 (2)	0.5183 (2)	0.25978 (12)	0.0561 (5)
C15	0.1226 (2)	0.3522 (2)	0.26160 (12)	0.0535 (4)
C16	0.2174 (2)	0.2820 (2)	0.17932 (12)	0.0541 (4)
H16	0.2666	0.1710	0.1810	0.065*
C17	0.0240 (3)	0.8792 (2)	0.09656 (15)	0.0776 (6)
H17A	0.1533	0.8797	0.0785	0.116*
H17B	−0.0321	0.9897	0.1101	0.116*
H17C	−0.0303	0.8391	0.0448	0.116*
C18	0.0640 (4)	0.6488 (3)	0.40255 (16)	0.1007 (8)
H18A	0.1511	0.5600	0.4234	0.151*
H18B	−0.0125	0.6940	0.4575	0.151*
H18C	0.1284	0.7337	0.3694	0.151*
C19	0.1573 (3)	0.0968 (3)	0.35144 (15)	0.0724 (6)
H19A	0.1064	0.0437	0.3030	0.109*
H19B	0.1190	0.0500	0.4137	0.109*
H19C	0.2889	0.0802	0.3399	0.109*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1024 (12)	0.0654 (10)	0.0810 (10)	0.0056 (8)	−0.0041 (8)	−0.0184 (8)
O2	0.0715 (8)	0.0709 (9)	0.0554 (7)	−0.0040 (7)	0.0000 (6)	−0.0128 (7)
O3	0.0942 (11)	0.0559 (8)	0.0699 (9)	0.0064 (7)	0.0051 (7)	0.0006 (7)
O4	0.0790 (9)	0.0789 (9)	0.0652 (8)	−0.0073 (7)	0.0123 (7)	−0.0120 (7)
O5	0.0813 (9)	0.0644 (8)	0.0575 (8)	−0.0123 (7)	0.0021 (6)	0.0062 (6)
N1	0.0542 (9)	0.0615 (10)	0.0526 (9)	−0.0109 (7)	−0.0033 (7)	−0.0048 (7)
C1	0.0636 (12)	0.0642 (13)	0.0608 (11)	−0.0072 (10)	−0.0074 (9)	−0.0108 (10)
C2	0.0492 (10)	0.0639 (12)	0.0564 (11)	−0.0098 (8)	−0.0043 (8)	−0.0124 (9)
C3	0.0531 (10)	0.0557 (11)	0.0561 (10)	−0.0084 (8)	−0.0068 (8)	−0.0067 (9)
C4	0.0490 (10)	0.0685 (12)	0.0537 (10)	−0.0114 (9)	−0.0047 (8)	−0.0052 (9)
C5	0.0624 (12)	0.0762 (14)	0.0563 (11)	−0.0055 (10)	−0.0022 (9)	−0.0031 (10)
C6	0.0673 (13)	0.0734 (14)	0.0740 (14)	−0.0078 (10)	−0.0058 (10)	0.0020 (11)
C7	0.0715 (13)	0.0897 (16)	0.0693 (13)	−0.0199 (12)	−0.0095 (11)	0.0132 (12)
C8	0.0985 (17)	0.0996 (18)	0.0541 (12)	−0.0228 (14)	−0.0034 (11)	−0.0001 (12)
C9	0.0891 (15)	0.0769 (14)	0.0570 (12)	−0.0157 (11)	−0.0004 (10)	−0.0088 (10)
C10	0.0578 (11)	0.0521 (10)	0.0613 (11)	−0.0089 (8)	−0.0086 (9)	−0.0049 (8)
C11	0.0502 (10)	0.0510 (10)	0.0530 (10)	−0.0107 (8)	−0.0063 (8)	−0.0042 (8)
C12	0.0585 (11)	0.0547 (11)	0.0520 (10)	−0.0098 (8)	−0.0044 (8)	0.0010 (8)
C13	0.0556 (10)	0.0509 (10)	0.0606 (11)	−0.0049 (8)	−0.0042 (9)	−0.0030 (9)
C14	0.0527 (10)	0.0600 (11)	0.0552 (10)	−0.0097 (8)	0.0014 (8)	−0.0076 (9)
C15	0.0521 (10)	0.0579 (11)	0.0519 (10)	−0.0137 (8)	−0.0054 (8)	0.0020 (8)
C16	0.0542 (10)	0.0495 (10)	0.0600 (11)	−0.0100 (8)	−0.0086 (8)	−0.0010 (8)
C17	0.0939 (16)	0.0551 (12)	0.0790 (14)	0.0018 (11)	−0.0067 (12)	0.0070 (10)
C18	0.146 (2)	0.0862 (17)	0.0716 (14)	−0.0273 (16)	0.0020 (15)	−0.0237 (12)
C19	0.0762 (13)	0.0681 (14)	0.0708 (13)	−0.0087 (11)	−0.0078 (11)	0.0161 (10)

Geometric parameters (Å, º) top

O1—C1	1.196 (2)	C8—C9	1.377 (3)
O2—C2	1.381 (2)	C8—H8	0.9300
O2—C1	1.393 (2)	C9—H9	0.9300
O3—C13	1.368 (2)	C10—C11	1.452 (2)
O3—C17	1.418 (2)	C10—H10	0.9300
O4—C14	1.368 (2)	C11—C16	1.391 (2)
O4—C18	1.418 (3)	C11—C12	1.396 (2)
O5—C15	1.363 (2)	C12—C13	1.374 (2)
O5—C19	1.417 (2)	C12—H12	0.9300
N1—C2	1.285 (2)	C13—C14	1.396 (3)
N1—C3	1.397 (2)	C14—C15	1.387 (3)
C1—C3	1.466 (3)	C15—C16	1.387 (2)
C2—C4	1.453 (3)	C16—H16	0.9300
C3—C10	1.345 (3)	C17—H17A	0.9600
C4—C5	1.380 (3)	C17—H17B	0.9600
C4—C9	1.387 (3)	C17—H17C	0.9600
C5—C6	1.371 (3)	C18—H18A	0.9600
C5—H5	0.9300	C18—H18B	0.9600
C6—C7	1.374 (3)	C18—H18C	0.9600
C6—H6	0.9300	C19—H19A	0.9600
C7—C8	1.361 (3)	C19—H19B	0.9600
C7—H7	0.9300	C19—H19C	0.9600

C2—O2—C1	105.35 (14)	C16—C11—C10	117.84 (16)
C13—O3—C17	117.23 (15)	C12—C11—C10	122.32 (16)
C14—O4—C18	113.61 (16)	C13—C12—C11	119.65 (16)
C15—O5—C19	117.33 (15)	C13—C12—H12	120.2
C2—N1—C3	105.67 (15)	C11—C12—H12	120.2
O1—C1—O2	121.82 (18)	O3—C13—C12	124.40 (16)
O1—C1—C3	133.22 (19)	O3—C13—C14	114.73 (16)
O2—C1—C3	104.96 (17)	C12—C13—C14	120.87 (17)
N1—C2—O2	115.89 (16)	O4—C14—C15	120.64 (16)
N1—C2—C4	126.61 (17)	O4—C14—C13	119.91 (17)
O2—C2—C4	117.50 (15)	C15—C14—C13	119.39 (16)
C10—C3—N1	129.17 (16)	O5—C15—C16	124.20 (16)
C10—C3—C1	122.71 (18)	O5—C15—C14	115.69 (16)
N1—C3—C1	108.10 (15)	C16—C15—C14	120.10 (16)
C5—C4—C9	118.72 (18)	C15—C16—C11	120.14 (16)
C5—C4—C2	119.35 (16)	C15—C16—H16	119.9
C9—C4—C2	121.92 (18)	C11—C16—H16	119.9
C6—C5—C4	120.99 (18)	O3—C17—H17A	109.5
C6—C5—H5	119.5	O3—C17—H17B	109.5
C4—C5—H5	119.5	H17A—C17—H17B	109.5
C5—C6—C7	119.7 (2)	O3—C17—H17C	109.5
C5—C6—H6	120.1	H17A—C17—H17C	109.5
C7—C6—H6	120.1	H17B—C17—H17C	109.5
C8—C7—C6	120.0 (2)	O4—C18—H18A	109.5
C8—C7—H7	120.0	O4—C18—H18B	109.5
C6—C7—H7	120.0	H18A—C18—H18B	109.5
C7—C8—C9	120.8 (2)	O4—C18—H18C	109.5
C7—C8—H8	119.6	H18A—C18—H18C	109.5
C9—C8—H8	119.6	H18B—C18—H18C	109.5
C8—C9—C4	119.8 (2)	O5—C19—H19A	109.5
C8—C9—H9	120.1	O5—C19—H19B	109.5
C4—C9—H9	120.1	H19A—C19—H19B	109.5
C3—C10—C11	129.81 (17)	O5—C19—H19C	109.5
C3—C10—H10	115.1	H19A—C19—H19C	109.5
C11—C10—H10	115.1	H19B—C19—H19C	109.5
C16—C11—C12	119.84 (16)

C2—O2—C1—O1	−179.16 (18)	C1—C3—C10—C11	−177.22 (17)
C2—O2—C1—C3	1.44 (18)	C3—C10—C11—C16	178.06 (17)
C3—N1—C2—O2	−0.07 (19)	C3—C10—C11—C12	−2.3 (3)
C3—N1—C2—C4	−179.39 (16)	C16—C11—C12—C13	0.5 (3)
C1—O2—C2—N1	−0.9 (2)	C10—C11—C12—C13	−179.12 (16)
C1—O2—C2—C4	178.45 (15)	C17—O3—C13—C12	−4.2 (3)
C2—N1—C3—C10	−177.93 (18)	C17—O3—C13—C14	176.14 (17)
C2—N1—C3—C1	1.01 (18)	C11—C12—C13—O3	179.96 (16)
O1—C1—C3—C10	−1.8 (3)	C11—C12—C13—C14	−0.4 (3)
O2—C1—C3—C10	177.47 (16)	C18—O4—C14—C15	87.7 (2)
O1—C1—C3—N1	179.2 (2)	C18—O4—C14—C13	−95.3 (2)
O2—C1—C3—N1	−1.55 (19)	O3—C13—C14—O4	2.2 (2)
N1—C2—C4—C5	10.3 (3)	C12—C13—C14—O4	−177.52 (16)
O2—C2—C4—C5	−168.97 (16)	O3—C13—C14—C15	179.23 (15)
N1—C2—C4—C9	−169.19 (18)	C12—C13—C14—C15	−0.5 (3)
O2—C2—C4—C9	11.5 (3)	C19—O5—C15—C16	−4.0 (2)
C9—C4—C5—C6	0.8 (3)	C19—O5—C15—C14	176.91 (16)
C2—C4—C5—C6	−178.80 (17)	O4—C14—C15—O5	−2.7 (2)
C4—C5—C6—C7	−0.5 (3)	C13—C14—C15—O5	−179.76 (15)
C5—C6—C7—C8	0.0 (3)	O4—C14—C15—C16	178.17 (15)
C6—C7—C8—C9	0.2 (3)	C13—C14—C15—C16	1.1 (3)
C7—C8—C9—C4	0.0 (3)	O5—C15—C16—C11	180.00 (15)
C5—C4—C9—C8	−0.5 (3)	C14—C15—C16—C11	−1.0 (3)
C2—C4—C9—C8	179.02 (19)	C12—C11—C16—C15	0.1 (2)
N1—C3—C10—C11	1.6 (3)	C10—C11—C16—C15	179.81 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1ⁱ	0.93	2.59	3.503 (2)	168
C6—H6···O3ⁱⁱ	0.93	2.62	3.420 (2)	144

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇NO₅
M_r	339.34
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	7.3897 (5), 8.1532 (6), 14.0023 (9)
α, β, γ (°)	86.917 (5), 83.306 (4), 82.471 (5)
V (Å³)	830.02 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.15 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.985, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	4665, 2904, 2056
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.121, 1.04
No. of reflections	2904
No. of parameters	229
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.15

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1ⁱ	0.93	2.59	3.503 (2)	168.1
C6—H6···O3ⁱⁱ	0.93	2.62	3.420 (2)	144.0

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

Acknowledgements

This project was supported by the Jiangsu Planned Projects for Postdoctoral Research Funds (grant No. 0701001B).

References

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