4-[(Ethoxy­imino)(phen­yl)meth­yl]-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one

Wang, J.-S.; Jiang, Y.-L.; Dong, W.-K.; Xu, L.; Kong, A.-P.

doi:10.1107/S1600536808026263

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1794

doi:10.1107/S1600536808026263

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4-[(Ethoxyimino)(phenyl)methyl]-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one

Jiu-Si Wang,^a Yan-Ling Jiang,^a Wen-Kui Dong,^a ^* Li Xu ^a and Ai-Ping Kong ^a

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: dongwk@mail.lzjtu.cn

(Received 12 August 2008; accepted 14 August 2008; online 20 August 2008)

In the molecule of the title compound, C₁₉H₁₉N₃O₂, the central pyrazole ring makes dihedral angles of 9.89 (3) and 66.06 (5)° with the two phenyl rings, and the two phenyl rings form an angle of 74.05 (5)°. An intramolecular C—H⋯O hydrogen bond forms a six-membered ring, producing an S(6) ring motif. In the crystal structure, intermolecular N—H⋯O and C—H⋯O hydrogen bonds link each molecule to two others, forming an infinite one-dimensional supramolecular structure along the c axis.

Related literature

For related literature, see: Beeam et al. (1984 ); Bonati (1980 ); Dong & Feng (2006 ); Dong et al. (2008a ,b ); Duan et al. (2007 ).

Experimental

Crystal data

C₁₉H₁₉N₃O₂
M_r = 321.37
Monoclinic, P 2₁ /c
a = 13.0046 (15) Å
b = 11.4657 (11) Å
c = 11.6874 (12) Å
β = 99.4530 (10)°
V = 1719.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.50 × 0.18 × 0.16 mm

Data collection

Brucker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.960, T_max = 0.987
8480 measured reflections
3028 independent reflections
1756 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.140
S = 1.02
3028 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O2ⁱ	0.86	1.80	2.653 (2)	171
C15—H15⋯O2ⁱ	0.93	2.42	3.200 (3)	141
C19—H19⋯O2	0.93	2.32	2.900 (3)	120
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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/S1600536808026263/zl2137sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808026263/zl2137Isup2.hkl

checkCIF report

Comment top

The pyrazole ring is a prominent structural motif found in numerous pharmaceutically active compounds. Due to the easy preparation and rich biological activity, the pyrazole framework plays an essential role in biologically active compounds and therefore represents an interesting template for combinatorial as well as medicinal chemistry (Beeam et al., 1984; Bonati et al., 1980). As an extension of our work (Dong et al., 2006; Duan et al., 2007; Dong et al., 2008a; Dong et al., 2008b) on the structural characterization of oxime compounds, the title compound, (Fig. 1), is reported here.

The single-crystal structure of the title compound is built up by only the C₁₉H₁₉N₃O₂ molecules, in which all bond lengths are in normal ranges. In the title compound, the central pyrazole ring makes dihedral angles of 9.89 (3) and 66.06 (5)° with the two outer benzene rings, and the two outer benzene rings form an angle of 74.05 (5)°. An intramolecular C—H···O hydrogen bond forms a six-membered ring, producing an S(6) ring motif. In the crystal structure, intermolecular N—H···O and C—H···O hydrogen bonds link each molecule to two others, forming an infinite one-dimensional supramolecular structure along the c axis (Fig. 2).

Related literature top

For related literature, see: Beeam et al. (1984); Bonati (1980); Dong & Feng (2006); Dong et al. (2008a,b); Duan et al. (2007).

Experimental top

To a solution of 1-phenyl-3-methyl-4-benzoyl-5-pyrazolon (5 mmol) in warm ethanol (5 ml) was added an ethanol (5 ml) solution of ethoxyamine (10 mmol). After stirring the reaction mixture at 338 K for 6 h, the solvent was removed under reduced pressure and the residue was recrystallized from ethanol to give the title compound. Yield, 68%. mp. 444–445 K. Anal. Calc. for C₁₉H₁₉N₃O₂: C, 71.01; H, 5.96; N, 13.08. Found: C, 71.32; H, 5.81; N, 13.15.

Colorless prismatic crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from ethanol at room temperature.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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. ORTEP representation of the title compound with atom numbering. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.
	Fig. 2. Part of the supramolecular structure of the title compound viewed along the b axis. Intra- and intermolecular hydrogen bonds are shown as dashed lines.

4-[(Ethoxyimino)(phenyl)methyl]-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one top

Crystal data top

C₁₉H₁₉N₃O₂	F(000) = 680
M_r = 321.37	D_x = 1.242 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1770 reflections
a = 13.0046 (15) Å	θ = 2.4–22.5°
b = 11.4657 (11) Å	µ = 0.08 mm⁻¹
c = 11.6874 (12) Å	T = 298 K
β = 99.453 (1)°	Prismatic, colorless
V = 1719.0 (3) Å³	0.50 × 0.18 × 0.16 mm
Z = 4

Data collection top

Brucker SMART 1000 CCD area-detector diffractometer	3028 independent reflections
Radiation source: fine-focus sealed tube	1756 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.960, T_max = 0.987	k = −13→9
8480 measured reflections	l = −13→13

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0687P)² + 0.0591P] where P = (F_o² + 2F_c²)/3
3028 reflections	(Δ/σ)_max < 0.001
219 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₉H₁₉N₃O₂	V = 1719.0 (3) Å³
M_r = 321.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.0046 (15) Å	µ = 0.08 mm⁻¹
b = 11.4657 (11) Å	T = 298 K
c = 11.6874 (12) Å	0.50 × 0.18 × 0.16 mm
β = 99.453 (1)°

Data collection top

Brucker SMART 1000 CCD area-detector diffractometer	3028 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1756 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.987	R_int = 0.041
8480 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.02	Δρ_max = 0.17 e Å⁻³
3028 reflections	Δρ_min = −0.24 e Å⁻³
219 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 > 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
N1	0.53222 (14)	0.34824 (17)	−0.06367 (17)	0.0486 (5)
N2	0.84502 (13)	0.23475 (16)	0.16076 (15)	0.0369 (5)
N3	0.78882 (13)	0.29323 (15)	0.23325 (15)	0.0386 (5)
H3	0.8064	0.2996	0.3072	0.046*
O1	0.49758 (11)	0.28139 (15)	0.02320 (14)	0.0546 (5)
O2	0.82634 (12)	0.20296 (15)	−0.03673 (13)	0.0529 (5)
C1	0.38665 (18)	0.2834 (2)	0.0039 (3)	0.0623 (8)
H1A	0.3595	0.2505	−0.0715	0.075*
H1B	0.3617	0.3630	0.0061	0.075*
C2	0.3515 (2)	0.2130 (3)	0.0975 (3)	0.0805 (10)
H2A	0.3776	0.1349	0.0954	0.121*
H2B	0.2767	0.2113	0.0859	0.121*
H2C	0.3774	0.2474	0.1715	0.121*
C3	0.63196 (17)	0.35862 (19)	−0.04638 (19)	0.0395 (6)
C4	0.70377 (15)	0.31546 (19)	0.05486 (18)	0.0363 (5)
C5	0.79385 (17)	0.24753 (19)	0.04860 (19)	0.0371 (5)
C6	0.70309 (16)	0.33834 (19)	0.17079 (19)	0.0360 (5)
C7	0.62708 (17)	0.4013 (2)	0.2301 (2)	0.0496 (7)
H7A	0.5735	0.3484	0.2446	0.074*
H7B	0.5964	0.4640	0.1817	0.074*
H7C	0.6622	0.4323	0.3023	0.074*
C8	0.67571 (18)	0.4228 (2)	−0.1379 (2)	0.0432 (6)
C9	0.6212 (2)	0.4282 (2)	−0.2505 (2)	0.0576 (7)
H9	0.5572	0.3908	−0.2688	0.069*
C10	0.6611 (3)	0.4881 (3)	−0.3347 (3)	0.0755 (9)
H10	0.6238	0.4914	−0.4097	0.091*
C11	0.7555 (3)	0.5432 (3)	−0.3093 (3)	0.0773 (9)
H11	0.7823	0.5832	−0.3671	0.093*
C12	0.8107 (2)	0.5397 (2)	−0.1988 (3)	0.0664 (8)
H12	0.8743	0.5782	−0.1811	0.080*
C13	0.77084 (19)	0.4782 (2)	−0.1138 (2)	0.0516 (7)
H13	0.8089	0.4743	−0.0393	0.062*
C14	0.94564 (15)	0.19033 (19)	0.20265 (19)	0.0358 (5)
C15	0.99788 (18)	0.2239 (2)	0.3093 (2)	0.0517 (7)
H15	0.9678	0.2775	0.3535	0.062*
C16	1.09499 (19)	0.1782 (3)	0.3508 (2)	0.0659 (8)
H16	1.1296	0.2005	0.4235	0.079*
C17	1.1406 (2)	0.1007 (3)	0.2862 (3)	0.0667 (8)
H17	1.2063	0.0706	0.3143	0.080*
C18	1.0891 (2)	0.0678 (2)	0.1801 (3)	0.0647 (8)
H18	1.1203	0.0153	0.1358	0.078*
C19	0.99121 (17)	0.1113 (2)	0.1374 (2)	0.0520 (7)
H19	0.9564	0.0875	0.0652	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0485 (12)	0.0550 (13)	0.0405 (13)	0.0035 (10)	0.0019 (10)	0.0055 (10)
N2	0.0349 (10)	0.0546 (12)	0.0209 (10)	0.0067 (8)	0.0036 (8)	0.0001 (9)
N3	0.0394 (10)	0.0560 (12)	0.0200 (10)	0.0020 (9)	0.0038 (8)	−0.0052 (9)
O1	0.0391 (9)	0.0719 (12)	0.0507 (11)	−0.0002 (8)	0.0010 (8)	0.0123 (9)
O2	0.0585 (10)	0.0778 (12)	0.0223 (9)	0.0200 (9)	0.0069 (8)	−0.0005 (8)
C1	0.0402 (14)	0.0705 (19)	0.073 (2)	0.0002 (13)	−0.0002 (14)	0.0023 (16)
C2	0.0532 (17)	0.109 (3)	0.080 (2)	−0.0073 (16)	0.0143 (16)	0.007 (2)
C3	0.0398 (13)	0.0446 (14)	0.0328 (13)	0.0031 (10)	0.0020 (10)	−0.0023 (11)
C4	0.0359 (12)	0.0465 (13)	0.0258 (13)	−0.0004 (10)	0.0034 (10)	0.0039 (10)
C5	0.0396 (12)	0.0490 (14)	0.0225 (12)	0.0010 (10)	0.0039 (10)	0.0016 (11)
C6	0.0354 (12)	0.0423 (13)	0.0297 (13)	−0.0027 (10)	0.0036 (10)	0.0004 (10)
C7	0.0479 (14)	0.0618 (16)	0.0400 (15)	0.0050 (12)	0.0098 (12)	−0.0069 (13)
C8	0.0518 (14)	0.0436 (14)	0.0332 (14)	0.0124 (12)	0.0038 (11)	0.0021 (11)
C9	0.0661 (17)	0.0619 (17)	0.0428 (17)	0.0110 (14)	0.0026 (14)	0.0081 (14)
C10	0.096 (2)	0.084 (2)	0.0456 (19)	0.0188 (19)	0.0093 (17)	0.0216 (17)
C11	0.101 (3)	0.076 (2)	0.062 (2)	0.0172 (19)	0.034 (2)	0.0259 (17)
C12	0.0723 (19)	0.0598 (18)	0.072 (2)	0.0014 (15)	0.0254 (17)	0.0119 (16)
C13	0.0570 (16)	0.0532 (16)	0.0447 (16)	0.0036 (13)	0.0088 (13)	0.0033 (13)
C14	0.0325 (12)	0.0446 (13)	0.0293 (13)	0.0011 (10)	0.0025 (10)	0.0048 (11)
C15	0.0437 (14)	0.0661 (17)	0.0423 (16)	0.0060 (12)	−0.0023 (12)	−0.0078 (13)
C16	0.0507 (16)	0.086 (2)	0.0528 (18)	0.0087 (15)	−0.0162 (14)	−0.0103 (16)
C17	0.0473 (15)	0.080 (2)	0.066 (2)	0.0174 (15)	−0.0093 (15)	0.0000 (17)
C18	0.0568 (16)	0.0708 (19)	0.065 (2)	0.0203 (14)	0.0056 (15)	−0.0057 (16)
C19	0.0487 (14)	0.0649 (17)	0.0395 (15)	0.0124 (13)	−0.0011 (12)	−0.0048 (13)

Geometric parameters (Å, º) top

N1—C3	1.285 (3)	C8—C13	1.378 (3)
N1—O1	1.404 (2)	C8—C9	1.389 (3)
N2—C5	1.377 (3)	C9—C10	1.371 (4)
N2—N3	1.380 (2)	C9—H9	0.9300
N2—C14	1.415 (3)	C10—C11	1.369 (4)
N3—C6	1.333 (3)	C10—H10	0.9300
N3—H3	0.8600	C11—C12	1.371 (4)
O1—C1	1.423 (3)	C11—H11	0.9300
O2—C5	1.254 (2)	C12—C13	1.386 (3)
C1—C2	1.491 (4)	C12—H12	0.9300
C1—H1A	0.9700	C13—H13	0.9300
C1—H1B	0.9700	C14—C15	1.373 (3)
C2—H2A	0.9600	C14—C19	1.379 (3)
C2—H2B	0.9600	C15—C16	1.380 (3)
C2—H2C	0.9600	C15—H15	0.9300
C3—C4	1.468 (3)	C16—C17	1.363 (3)
C3—C8	1.487 (3)	C16—H16	0.9300
C4—C6	1.382 (3)	C17—C18	1.362 (4)
C4—C5	1.419 (3)	C17—H17	0.9300
C6—C7	1.485 (3)	C18—C19	1.383 (3)
C7—H7A	0.9600	C18—H18	0.9300
C7—H7B	0.9600	C19—H19	0.9300
C7—H7C	0.9600

C3—N1—O1	111.86 (18)	H7B—C7—H7C	109.5
C5—N2—N3	108.11 (16)	C13—C8—C9	118.3 (2)
C5—N2—C14	130.00 (18)	C13—C8—C3	121.2 (2)
N3—N2—C14	121.03 (17)	C9—C8—C3	120.5 (2)
C6—N3—N2	109.39 (17)	C10—C9—C8	120.5 (3)
C6—N3—H3	125.3	C10—C9—H9	119.7
N2—N3—H3	125.3	C8—C9—H9	119.7
N1—O1—C1	108.28 (17)	C11—C10—C9	120.5 (3)
O1—C1—C2	107.5 (2)	C11—C10—H10	119.7
O1—C1—H1A	110.2	C9—C10—H10	119.7
C2—C1—H1A	110.2	C10—C11—C12	120.2 (3)
O1—C1—H1B	110.2	C10—C11—H11	119.9
C2—C1—H1B	110.2	C12—C11—H11	119.9
H1A—C1—H1B	108.5	C11—C12—C13	119.4 (3)
C1—C2—H2A	109.5	C11—C12—H12	120.3
C1—C2—H2B	109.5	C13—C12—H12	120.3
H2A—C2—H2B	109.5	C8—C13—C12	121.1 (3)
C1—C2—H2C	109.5	C8—C13—H13	119.5
H2A—C2—H2C	109.5	C12—C13—H13	119.5
H2B—C2—H2C	109.5	C15—C14—C19	119.5 (2)
N1—C3—C4	126.0 (2)	C15—C14—N2	120.3 (2)
N1—C3—C8	115.4 (2)	C19—C14—N2	120.1 (2)
C4—C3—C8	118.62 (19)	C14—C15—C16	120.0 (2)
C6—C4—C5	107.05 (19)	C14—C15—H15	120.0
C6—C4—C3	128.4 (2)	C16—C15—H15	120.0
C5—C4—C3	124.40 (19)	C17—C16—C15	120.6 (3)
O2—C5—N2	122.71 (19)	C17—C16—H16	119.7
O2—C5—C4	130.8 (2)	C15—C16—H16	119.7
N2—C5—C4	106.46 (18)	C18—C17—C16	119.4 (2)
N3—C6—C4	108.91 (19)	C18—C17—H17	120.3
N3—C6—C7	119.62 (19)	C16—C17—H17	120.3
C4—C6—C7	131.5 (2)	C17—C18—C19	121.0 (3)
C6—C7—H7A	109.5	C17—C18—H18	119.5
C6—C7—H7B	109.5	C19—C18—H18	119.5
H7A—C7—H7B	109.5	C14—C19—C18	119.4 (2)
C6—C7—H7C	109.5	C14—C19—H19	120.3
H7A—C7—H7C	109.5	C18—C19—H19	120.3

C5—N2—N3—C6	2.1 (2)	N1—C3—C8—C13	155.2 (2)
C14—N2—N3—C6	172.45 (18)	C4—C3—C8—C13	−23.6 (3)
C3—N1—O1—C1	174.5 (2)	N1—C3—C8—C9	−24.8 (3)
N1—O1—C1—C2	−179.5 (2)	C4—C3—C8—C9	156.4 (2)
O1—N1—C3—C4	−4.5 (3)	C13—C8—C9—C10	−0.6 (4)
O1—N1—C3—C8	176.79 (17)	C3—C8—C9—C10	179.4 (2)
N1—C3—C4—C6	−55.2 (4)	C8—C9—C10—C11	0.3 (4)
C8—C3—C4—C6	123.5 (2)	C9—C10—C11—C12	−0.5 (4)
N1—C3—C4—C5	130.1 (2)	C10—C11—C12—C13	1.1 (4)
C8—C3—C4—C5	−51.3 (3)	C9—C8—C13—C12	1.1 (3)
N3—N2—C5—O2	−179.5 (2)	C3—C8—C13—C12	−178.9 (2)
C14—N2—C5—O2	11.3 (4)	C11—C12—C13—C8	−1.4 (4)
N3—N2—C5—C4	−0.3 (2)	C5—N2—C14—C15	155.0 (2)
C14—N2—C5—C4	−169.5 (2)	N3—N2—C14—C15	−13.0 (3)
C6—C4—C5—O2	177.7 (2)	C5—N2—C14—C19	−26.1 (3)
C3—C4—C5—O2	−6.7 (4)	N3—N2—C14—C19	165.9 (2)
C6—C4—C5—N2	−1.4 (2)	C19—C14—C15—C16	−0.4 (4)
C3—C4—C5—N2	174.25 (19)	N2—C14—C15—C16	178.5 (2)
N2—N3—C6—C4	−3.0 (2)	C14—C15—C16—C17	0.9 (4)
N2—N3—C6—C7	177.33 (17)	C15—C16—C17—C18	−0.5 (4)
C5—C4—C6—N3	2.8 (2)	C16—C17—C18—C19	−0.3 (4)
C3—C4—C6—N3	−172.7 (2)	C15—C14—C19—C18	−0.4 (4)
C5—C4—C6—C7	−177.7 (2)	N2—C14—C19—C18	−179.3 (2)
C3—C4—C6—C7	6.9 (4)	C17—C18—C19—C14	0.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2ⁱ	0.86	1.80	2.653 (2)	171
C15—H15···O2ⁱ	0.93	2.42	3.200 (3)	141
C19—H19···O2	0.93	2.32	2.900 (3)	120

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉N₃O₂
M_r	321.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	13.0046 (15), 11.4657 (11), 11.6874 (12)
β (°)	99.453 (1)
V (Å³)	1719.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.18 × 0.16

Data collection
Diffractometer	Brucker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.960, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	8480, 3028, 1756
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.140, 1.02
No. of reflections	3028
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.24

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), 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
N3—H3···O2ⁱ	0.860	1.800	2.653 (2)	170.88
C15—H15···O2ⁱ	0.930	2.420	3.200 (3)	141.00
C19—H19···O2	0.930	2.320	2.900 (3)	120.00

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

This work was supported by the Foundation of the Education Department of Gansu Province (No. 0604–01) and the `Qing Lan' Talent Engineering Funds of Lanzhou Jiaotong University (No. QL-03–01 A), which are gratefully acknowledged.

References

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