4-[(3-Meth­oxy­anilino)methyl­idene]-2-phenyl-1,3-oxazol-5(4H)-one

Huang, W.-Y.; Zhang, Y.; Hu, K.; Lin, Q.-M.; Liu, X.-X.

doi:10.1107/S1600536812008276

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1008

doi:10.1107/S1600536812008276

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4-[(3-Methoxyanilino)methylidene]-2-phenyl-1,3-oxazol-5(4H)-one

Wan-Yun Huang,^a Ye Zhang,^a Kun Hu,^b Qing-Mei Lin ^b and Xian-Xian Liu ^a ^*

^aDepartment of Chemistry, Guilin Normal College, Xinyi Road 21, Guilin 541001, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Guangxi Normal University, Yucai Road 15, Guilin 541004, People's Republic of China
^*Correspondence e-mail: lizhangdong2005@163.com

(Received 1 February 2012; accepted 24 February 2012; online 10 March 2012)

In the title compound, C₁₇H₁₄N₂O₃, the oxazolone ring is essentially planar [maximum deviation = 0.004 (1) Å] and is oriented with respect to the phenyl and benzene rings at 10.06 (9) and 5.63 (8)°, respectively; the dihedral angle between the phenyl ring and the benzene ring is 15.69 (8)°. In the crystal, N—H⋯O hydrogen bonds link the molecules into chains running along the a axis. Neighbouring chains are interconnected by π–π stacking, the centroid–centroid distance being 3.6201 (9) Å.

Related literature

For background to the oxazolones, see: Fisk et al. (2007 ); Mosey et al. (2008 ); Hewlett et al. (2009 ). For the bioactivities of 4-(aminomethylene)-2-phenyl-4H-oxazol-5-one derivatives, see: Tandon et al. (2004 ); John et al. (2008 ). For the synthesis, see: Matos et al. (2003 ). For related structures, see: Romeiro et al. (2010 ); Vasuki et al. (2002 ).

Experimental

Crystal data

C₁₇H₁₄N₂O₃
M_r = 294.30
Triclinic, $[P \overline 1]$
a = 6.6085 (5) Å
b = 7.1887 (5) Å
c = 15.3659 (10) Å
α = 98.629 (5)°
β = 94.096 (5)°
γ = 108.715 (6)°
V = 677.96 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 150 K
0.25 × 0.20 × 0.15 mm

Data collection

Agilent SuperNova (single source at offset) Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.975, T_max = 0.985
5557 measured reflections
2759 independent reflections
2317 reflections with I > 2σ(I)
R_int = 0.023
Standard reflections: 0

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.118
S = 1.02
2759 reflections
204 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 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
N2—H2A⋯O1ⁱ	0.92 (2)	2.26 (2)	3.0110 (18)	138.1 (17)
Symmetry code: (i) x+1, y, z.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812008276/xu5464sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812008276/xu5464Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812008276/xu5464Isup3.cml

checkCIF report

Comment top

Oxazolones are heterocyclic compounds which serve as a very important role in the synthesis of amino acids, peptides and natural product (Fisk et al., 2007; Mosey et al., 2008; Hewlett et al., 2009). Among them, 4- (aminomethylene)-2-phenyl-4H-oxazol-5-one derivatives show a range of interesting and medicinally relevant bioactivities (Tandon et al., 2004; John et al., 2008). Recently, Romeiro reported the crystal structure of the 4-[(Dimethylamino)methylidene]-2- (4-nitrophenyl)-1,3-oxazol-5(4H)-one (Romeiro et al., 2010). Herein, we wish to report the synthesis and crystal structure of 4-[(3-Methoxy-phenylamino)-methylene]-2- phenyl-4H-oxazol-5-one. The molecule with the Z-configuration (Fig. 1) of the title compound is planar with the maximum deviations from the least-squares plane through all non-hydrogen atoms being 0.292 Å for atom C4 and -0.237 Å for atom C1; the r.m.s. = 0.089 Å. The sequence of C7—N1, N1—C9, C9—C10, C10—N2, and N2—C11 bond distances of 1.2917 (19), 1.407 (2), 1.372 (2), 1.337 (2), and 1.4201 (19) Å, respectively, indicate substantial delocalization of π-electron density over these atoms. The geometric parameters match closely those related structure (Romeiro et al., 2010; Vasuki et al., 2002). The crystal packing is dominated by N—H···O and π-π interactions. An intermolecular N(2)—H(2 A)···O(1) (Symmetry code: x + 1, y, z) hydrogen bond (Table 1) link the molecule into a one-dimensional chain along the a axis (Fig. 2). And the neighbouring chains are interconnected by π-π stacking interactions occurring between oxazolin-5-one and the 3-methoxy-phenyl ring with a centroid-centroid distance of 3.62 Å, which lead to form a two-dimensional network (Fig. 3).

Related literature top

For background to the oxazolones, see: Fisk et al. (2007); Mosey et al. (2008); Hewlett et al. (2009). For the bioactivities of 4-(aminomethylene)-2-phenyl-4H-oxazol-5-one derivatives, see: Tandon et al. (2004); John et al. (2008). For the synthesis, see: Matos et al. (2003). For related structures, see: Romeiro et al. (2010); Vasuki et al. (2002).

Experimental top

A mixture of 4-ethoxymethylene-2-phenyl-4H-oxazol-5-one (Matos et al., 2003) (0.01 mol) and 3-methoxy-phenylamine (0.01 mol) in THF (25 ml) was stirred at room temperature for 4 h. The solvent was then evaporated under reduced pressure and the residue was crystallized from ethyl acetate to give orange crystals suitable for X-ray analysis (yield 82%).

Structure description top

For background to the oxazolones, see: Fisk et al. (2007); Mosey et al. (2008); Hewlett et al. (2009). For the bioactivities of 4-(aminomethylene)-2-phenyl-4H-oxazol-5-one derivatives, see: Tandon et al. (2004); John et al. (2008). For the synthesis, see: Matos et al. (2003). For related structures, see: Romeiro et al. (2010); Vasuki et al. (2002).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atomic labeling scheme with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A view of the one-dimensional chain along a axis sustained by N(2)—H(2 A)···O(1)(i) ((i) x + 1, y, z) hydrogen bond (shown as dashed lines).
	Fig. 3. View of the two-dimensional network constructed by hydrogen bond and π-π interactions shown as green and purple dashed lines respectively.

4-[(3-Methoxyanilino)methylidene]-2-phenyl-1,3-oxazol-5(4H)-one top

Crystal data top

C₁₇H₁₄N₂O₃	Z = 2
M_r = 294.30	F(000) = 308
Triclinic, P1	D_x = 1.442 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6085 (5) Å	Cell parameters from 2524 reflections
b = 7.1887 (5) Å	θ = 3.0–28.7°
c = 15.3659 (10) Å	µ = 0.10 mm⁻¹
α = 98.629 (5)°	T = 150 K
β = 94.096 (5)°	Block, green
γ = 108.715 (6)°	0.25 × 0.20 × 0.15 mm
V = 677.96 (8) Å³

Data collection top

Agilent SuperNova (single source at offset) Eos diffractometer	2759 independent reflections
Radiation source: fine-focus sealed tube	2317 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 26.4°, θ_min = 3.0°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −8→8
T_min = 0.975, T_max = 0.985	k = −8→8
5557 measured reflections	l = −19→19

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) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.060P)² + 0.1704P] where P = (F_o² + 2F_c²)/3
2759 reflections	(Δ/σ)_max < 0.001
204 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₇H₁₄N₂O₃	γ = 108.715 (6)°
M_r = 294.30	V = 677.96 (8) Å³
Triclinic, P1	Z = 2
a = 6.6085 (5) Å	Mo Kα radiation
b = 7.1887 (5) Å	µ = 0.10 mm⁻¹
c = 15.3659 (10) Å	T = 150 K
α = 98.629 (5)°	0.25 × 0.20 × 0.15 mm
β = 94.096 (5)°

Data collection top

Agilent SuperNova (single source at offset) Eos diffractometer	2759 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2317 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.985	R_int = 0.023
5557 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.22 e Å⁻³
2759 reflections	Δρ_min = −0.29 e Å⁻³
204 parameters

Special details top

Experimental. ¹H NMR (DMSO, 500 MHz) δ: 10.70 (d, 1H, NH), 7.97–8.05 (m, 3H, Ar—H), 7.55–7.57(m, 3H, Ar—H), 7.25 (t, 1H, Ar—H), 7.10–7.14 (m, 2H, Ar—H), 6.67 (q, 1H, Ar—H), 3.78 (s, 3H, CH3). ¹³C NMR (DMSO, 125.77 MHz) δ: 167.11, 160.27, 154.44, 141.21, 135.31, 131.34, 130.28, 129.09, 126.55, 126.40, 125.82, 111.06, 109.81, 109.29, 102.70, 55.23.

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
C1	0.2537 (3)	0.6133 (3)	0.85604 (11)	0.0242 (4)
H1	0.3396	0.5732	0.8151	0.029*
C2	0.3478 (3)	0.7213 (3)	0.93963 (11)	0.0311 (4)
H2	0.4981	0.7544	0.9562	0.037*
C3	0.2225 (3)	0.7811 (3)	0.99922 (11)	0.0318 (4)
H3	0.2876	0.8552	1.0565	0.038*
C4	0.0043 (3)	0.7337 (3)	0.97570 (11)	0.0297 (4)
H4	−0.0803	0.7762	1.0165	0.036*
C5	−0.0917 (3)	0.6238 (3)	0.89242 (11)	0.0243 (4)
H5	−0.2425	0.5895	0.8766	0.029*
C6	0.0327 (2)	0.5636 (2)	0.83184 (10)	0.0189 (3)
C7	−0.0642 (2)	0.4518 (2)	0.74310 (10)	0.0176 (3)
C8	−0.3384 (3)	0.2824 (2)	0.63810 (10)	0.0192 (3)
C9	−0.1337 (2)	0.3036 (2)	0.60730 (10)	0.0177 (3)
C10	−0.1006 (2)	0.2327 (2)	0.52347 (10)	0.0177 (3)
H10	−0.2216	0.1660	0.4796	0.021*
C11	0.1565 (3)	0.2043 (2)	0.41664 (9)	0.0179 (3)
C12	0.3751 (3)	0.2674 (2)	0.40875 (10)	0.0194 (3)
H12	0.4774	0.3409	0.4588	0.023*
C13	0.4433 (3)	0.2222 (2)	0.32722 (10)	0.0214 (4)
H13	0.5925	0.2669	0.3213	0.026*
C14	0.2950 (3)	0.1127 (2)	0.25468 (10)	0.0220 (4)
H14	0.3422	0.0818	0.1991	0.026*
C15	0.0758 (3)	0.0477 (2)	0.26330 (10)	0.0184 (3)
C16	0.0038 (2)	0.0943 (2)	0.34428 (10)	0.0184 (3)
H16	−0.1457	0.0522	0.3499	0.022*
C17	−0.2821 (3)	−0.1308 (3)	0.19348 (11)	0.0292 (4)
H17A	−0.3122	−0.2117	0.2400	0.044*
H17B	−0.3592	−0.2118	0.1364	0.044*
H17C	−0.3300	−0.0154	0.2077	0.044*
N1	0.0328 (2)	0.41031 (19)	0.67659 (8)	0.0183 (3)
N2	0.0970 (2)	0.2548 (2)	0.50167 (9)	0.0194 (3)
O1	−0.52599 (17)	0.20389 (18)	0.60520 (7)	0.0254 (3)
O2	−0.28635 (16)	0.38163 (16)	0.72695 (7)	0.0195 (3)
O3	−0.05667 (17)	−0.06328 (17)	0.18811 (7)	0.0235 (3)
H2A	0.211 (3)	0.304 (3)	0.5461 (13)	0.036 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0235 (9)	0.0242 (9)	0.0223 (8)	0.0044 (7)	0.0045 (7)	0.0031 (7)
C2	0.0262 (9)	0.0315 (10)	0.0271 (9)	0.0013 (8)	−0.0029 (7)	0.0013 (8)
C3	0.0432 (11)	0.0260 (10)	0.0179 (8)	0.0048 (8)	−0.0032 (8)	−0.0026 (7)
C4	0.0415 (11)	0.0292 (10)	0.0195 (8)	0.0148 (8)	0.0068 (8)	0.0006 (7)
C5	0.0278 (9)	0.0256 (9)	0.0211 (8)	0.0117 (7)	0.0037 (7)	0.0033 (7)
C6	0.0229 (8)	0.0160 (8)	0.0172 (8)	0.0054 (6)	0.0026 (6)	0.0043 (6)
C7	0.0183 (8)	0.0166 (8)	0.0189 (8)	0.0063 (6)	0.0037 (6)	0.0046 (6)
C8	0.0226 (9)	0.0213 (8)	0.0153 (7)	0.0096 (7)	0.0034 (6)	0.0030 (6)
C9	0.0182 (8)	0.0186 (8)	0.0167 (7)	0.0066 (6)	0.0029 (6)	0.0034 (6)
C10	0.0190 (8)	0.0176 (8)	0.0174 (7)	0.0074 (6)	0.0016 (6)	0.0031 (6)
C11	0.0244 (8)	0.0161 (8)	0.0161 (8)	0.0098 (6)	0.0053 (6)	0.0038 (6)
C12	0.0200 (8)	0.0185 (8)	0.0188 (8)	0.0061 (6)	0.0022 (6)	0.0018 (6)
C13	0.0199 (8)	0.0222 (9)	0.0233 (8)	0.0076 (7)	0.0070 (7)	0.0047 (7)
C14	0.0247 (9)	0.0258 (9)	0.0178 (8)	0.0106 (7)	0.0086 (7)	0.0035 (7)
C15	0.0225 (8)	0.0172 (8)	0.0163 (7)	0.0075 (6)	0.0022 (6)	0.0034 (6)
C16	0.0176 (8)	0.0200 (8)	0.0201 (8)	0.0085 (6)	0.0056 (6)	0.0052 (6)
C17	0.0196 (9)	0.0384 (11)	0.0251 (9)	0.0087 (8)	0.0001 (7)	−0.0043 (7)
N1	0.0184 (7)	0.0196 (7)	0.0170 (6)	0.0064 (5)	0.0037 (5)	0.0028 (5)
N2	0.0170 (7)	0.0246 (8)	0.0156 (7)	0.0073 (6)	0.0025 (5)	0.0001 (5)
O1	0.0177 (6)	0.0362 (7)	0.0209 (6)	0.0083 (5)	0.0005 (5)	0.0030 (5)
O2	0.0157 (6)	0.0264 (6)	0.0151 (5)	0.0068 (5)	0.0031 (4)	−0.0003 (4)
O3	0.0217 (6)	0.0296 (7)	0.0158 (6)	0.0059 (5)	0.0027 (5)	−0.0002 (5)

Geometric parameters (Å, º) top

C1—C2	1.384 (2)	C10—N2	1.337 (2)
C1—C6	1.395 (2)	C10—H10	0.9500
C1—H1	0.9500	C11—C12	1.389 (2)
C2—C3	1.388 (3)	C11—C16	1.394 (2)
C2—H2	0.9500	C11—N2	1.4201 (19)
C3—C4	1.378 (3)	C12—C13	1.389 (2)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.387 (2)	C13—C14	1.381 (2)
C4—H4	0.9500	C13—H13	0.9500
C5—C6	1.396 (2)	C14—C15	1.395 (2)
C5—H5	0.9500	C14—H14	0.9500
C6—C7	1.460 (2)	C15—O3	1.3670 (19)
C7—N1	1.2917 (19)	C15—C16	1.396 (2)
C7—O2	1.3810 (18)	C16—H16	0.9500
C8—O1	1.2191 (19)	C17—O3	1.4237 (19)
C8—O2	1.4051 (18)	C17—H17A	0.9800
C8—C9	1.435 (2)	C17—H17B	0.9800
C9—C10	1.372 (2)	C17—H17C	0.9800
C9—N1	1.407 (2)	N2—H2A	0.92 (2)

C2—C1—C6	120.00 (16)	C12—C11—C16	121.14 (14)
C2—C1—H1	120.0	C12—C11—N2	116.95 (14)
C6—C1—H1	120.0	C16—C11—N2	121.90 (14)
C1—C2—C3	120.03 (17)	C13—C12—C11	119.60 (15)
C1—C2—H2	120.0	C13—C12—H12	120.2
C3—C2—H2	120.0	C11—C12—H12	120.2
C4—C3—C2	120.38 (16)	C14—C13—C12	120.30 (15)
C4—C3—H3	119.8	C14—C13—H13	119.8
C2—C3—H3	119.8	C12—C13—H13	119.8
C3—C4—C5	120.01 (16)	C13—C14—C15	119.82 (14)
C3—C4—H4	120.0	C13—C14—H14	120.1
C5—C4—H4	120.0	C15—C14—H14	120.1
C4—C5—C6	120.10 (16)	O3—C15—C14	115.12 (13)
C4—C5—H5	119.9	O3—C15—C16	124.11 (14)
C6—C5—H5	119.9	C14—C15—C16	120.77 (15)
C1—C6—C5	119.48 (15)	C11—C16—C15	118.35 (14)
C1—C6—C7	119.49 (14)	C11—C16—H16	120.8
C5—C6—C7	121.03 (15)	C15—C16—H16	120.8
N1—C7—O2	115.14 (13)	O3—C17—H17A	109.5
N1—C7—C6	127.89 (14)	O3—C17—H17B	109.5
O2—C7—C6	116.97 (13)	H17A—C17—H17B	109.5
O1—C8—O2	120.54 (14)	O3—C17—H17C	109.5
O1—C8—C9	135.12 (15)	H17A—C17—H17C	109.5
O2—C8—C9	104.33 (13)	H17B—C17—H17C	109.5
C10—C9—N1	124.09 (14)	C7—N1—C9	104.91 (13)
C10—C9—C8	126.24 (15)	C10—N2—C11	128.04 (14)
N1—C9—C8	109.67 (13)	C10—N2—H2A	118.3 (12)
N2—C10—C9	121.89 (15)	C11—N2—H2A	113.6 (13)
N2—C10—H10	119.1	C7—O2—C8	105.95 (11)
C9—C10—H10	119.1	C15—O3—C17	117.09 (12)

C6—C1—C2—C3	−0.4 (3)	C12—C13—C14—C15	0.2 (2)
C1—C2—C3—C4	0.0 (3)	C13—C14—C15—O3	−178.56 (13)
C2—C3—C4—C5	0.6 (3)	C13—C14—C15—C16	0.9 (2)
C3—C4—C5—C6	−0.9 (3)	C12—C11—C16—C15	0.4 (2)
C2—C1—C6—C5	0.1 (2)	N2—C11—C16—C15	−178.82 (13)
C2—C1—C6—C7	179.27 (15)	O3—C15—C16—C11	178.24 (13)
C4—C5—C6—C1	0.5 (2)	C14—C15—C16—C11	−1.2 (2)
C4—C5—C6—C7	−178.59 (14)	O2—C7—N1—C9	0.53 (17)
C1—C6—C7—N1	−9.5 (2)	C6—C7—N1—C9	−179.07 (14)
C5—C6—C7—N1	169.59 (15)	C10—C9—N1—C7	179.11 (14)
C1—C6—C7—O2	170.88 (13)	C8—C9—N1—C7	−0.69 (16)
C5—C6—C7—O2	−10.0 (2)	C9—C10—N2—C11	−174.39 (14)
O1—C8—C9—C10	0.7 (3)	C12—C11—N2—C10	171.24 (15)
O2—C8—C9—C10	−179.20 (14)	C16—C11—N2—C10	−9.5 (2)
O1—C8—C9—N1	−179.47 (17)	N1—C7—O2—C8	−0.17 (17)
O2—C8—C9—N1	0.59 (16)	C6—C7—O2—C8	179.48 (12)
N1—C9—C10—N2	2.3 (2)	O1—C8—O2—C7	179.78 (14)
C8—C9—C10—N2	−177.99 (14)	C9—C8—O2—C7	−0.27 (15)
C16—C11—C12—C13	0.7 (2)	C14—C15—O3—C17	−179.23 (14)
N2—C11—C12—C13	179.92 (14)	C16—C15—O3—C17	1.3 (2)
C11—C12—C13—C14	−1.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.92 (2)	2.26 (2)	3.0110 (18)	138.1 (17)

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄N₂O₃
M_r	294.30
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	6.6085 (5), 7.1887 (5), 15.3659 (10)
α, β, γ (°)	98.629 (5), 94.096 (5), 108.715 (6)
V (Å³)	677.96 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Agilent SuperNova (single source at offset) Eos
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.975, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	5557, 2759, 2317
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.118, 1.02
No. of reflections	2759
No. of parameters	204
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.29

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.92 (2)	2.26 (2)	3.0110 (18)	138.1 (17)

Symmetry code: (i) x+1, y, z.

Acknowledgements

The authors thank the Science Foundation of Guilin Normal College (grant No. 2008), Guilin Scientific Research and Technological Development Projects (grant No. 20110106-2) and Guangxi University Scientific Research Projects (grant No. 200103YB159).

References

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