1-(4-Isopropyl­phen­yl)-5-(4-methoxy­phen­yl)pyrazolidin-3-one

Jia, H.-S.; Li, Y.-F.; Liu, Y.-Y.; Liu, S.; Zhu, H.-J.

doi:10.1107/S1600536808009823

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o855

doi:10.1107/S1600536808009823

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1-(4-Isopropylphenyl)-5-(4-methoxyphenyl)pyrazolidin-3-one

Hong-Sheng Jia,^a Yu-Feng Li,^a Yuan-Yuan Liu,^a Shan Liu ^a and Hong-Jun Zhu ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: zhuhj@njut.edu.cn

(Received 7 April 2008; accepted 10 April 2008; online 16 April 2008)

In the molecule of the title compound, C₁₉H₂₂N₂O₂, the pyrazolidinone ring has an envelope conformation, with the C atom attached to the 4-methoxyphenyl ring displaced by 0.354 (3) Å from the plane of the other ring atoms. The 4-isopropylphenyl ring is oriented with respect to the 4-methoxyphenyl ring at a dihedral angle of 88.94 (3)°. Intramolecular C—H⋯N hydrogen bonds result in the formation of two planar five-membered rings, which are oriented with respect to the adjacent 4-isopropylphenyl and 4-methoxyphenyl rings at dihedral angles of 4.05 (3) and 0.50 (3)°, respectively. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For general background, see: Menozzi et al. (1990 ); Brooks et al. (1990 ); Greenwood et al. (1995 ).

Experimental

Crystal data

C₁₉H₂₂N₂O₂
M_r = 310.39
Monoclinic, P 2₁ /n
a = 14.737 (3) Å
b = 7.1490 (14) Å
c = 17.493 (4) Å
β = 112.03 (3)°
V = 1708.4 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 294 (2) K
0.40 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.969, T_max = 0.984
3472 measured reflections
3340 independent reflections
1835 reflections with I > 2σ(I)
R_int = 0.052
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.078
wR(F²) = 0.163
S = 1.06
3340 reflections
202 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.78 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.86	1.96	2.819 (4)	175
C8—H8A⋯N2	0.93	2.44	2.761 (5)	100
C14—H14A⋯N1	0.93	2.54	2.887 (5)	102
Symmetry code: (i) -x+1, -y+2, -z+2.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009823/hk2451sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808009823/hk2451Isup2.hkl

checkCIF report

Comment top

Pyrazolidin-3-one derivatives are important chemical materials of effective medicines used for treatment of inflammation. They are of great interest because of their biological properties, such as antipyretic activity (Menozzi et al., 1990), liphoxygenase enzyme inhibition (Brooks et al., 1990) and cholecystokinin (CCK) receptor antagonist activity (Greenwood et al., 1995). We report herein the crystal structure of the title compound, (I).

In the molecule of (I), (Fig. 1), rings A (C4-C9) and C (C13-C18) are, of course, planar. The dihedral angle between them is A/C = 88.94 (3)°. Ring B (N1/N2/C10-C12) has envelope conformation with atom C10 displaced by 0.354 (3) Å from the plane of the other ring atoms. The intramolecular C-H···N hydrogen bonds (Table 1) result in the formation of two planar five-membered rings D (N1/N2/C7/C8/H8A) and E (N1/C10/C13/C14/H14A). They are oriented with respect to the adjacent rings at dihedral angles of A/D = 4.05 (3)° and C/E = 0.50 (3)°. So, they are also nearly coplanar.

In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For general background, see: Menozzi et al. (1990); Brooks et al. (1990); Greenwood et al. (1995).

Experimental top

For the preparation of the title compound, ethanolamine (4 ml) and n-butanol (20 ml) were added to a solution of sodium (40 mmol) in anhydrous methanol (9 mol). Then, the methanol was removed by distillation and 3-(4-methylphenyl) acrylate was added. The mixture was refluxed for 1 h at the temperature above 373 K, after which isopropyphenyl hydrazine (4 ml) was added. The reactants were refluxed for a further 10 h, left to cool to room temperature, and then acidified with acetic acid (36%), allowed to stand, filtered, and the filter cake was crystallized from ethyl acetate to give the title compound (m.p. 435-437 K). It was crystallized by the slow evaporation of an ethyl acetate solution.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bond is shown as dashed line.
	Fig. 2. A partial packing diagram of (I). Hydrogen bonds are shown as dashed lines.

1-(4-Isopropylphenyl)-5-(4-methoxyphenyl)pyrazolidin-3-one top

Crystal data top

C₁₉H₂₂N₂O₂	F(000) = 664
M_r = 310.39	D_x = 1.207 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 14.737 (3) Å	θ = 9–13°
b = 7.1490 (14) Å	µ = 0.08 mm⁻¹
c = 17.493 (4) Å	T = 294 K
β = 112.03 (3)°	Block, colorless
V = 1708.4 (7) Å³	0.40 × 0.30 × 0.20 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1835 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.052
Graphite monochromator	θ_max = 26.0°, θ_min = 1.6°
ω/2θ scans	h = −18→16
Absorption correction: ψ scan (North et al., 1968)	k = 0→8
T_min = 0.969, T_max = 0.984	l = 0→21
3472 measured reflections	3 standard reflections every 120 min
3340 independent reflections	intensity decay: none

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.008P)² + 3.2P] where P = (F_o² + 2F_c²)/3
3340 reflections	(Δ/σ)_max < 0.001
202 parameters	Δρ_max = 0.38 e Å⁻³
1 restraint	Δρ_min = −0.78 e Å⁻³

Crystal data top

C₁₉H₂₂N₂O₂	V = 1708.4 (7) Å³
M_r = 310.39	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.737 (3) Å	µ = 0.08 mm⁻¹
b = 7.1490 (14) Å	T = 294 K
c = 17.493 (4) Å	0.40 × 0.30 × 0.20 mm
β = 112.03 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1835 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.052
T_min = 0.969, T_max = 0.984	3 standard reflections every 120 min
3472 measured reflections	intensity decay: none
3340 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.078	1 restraint
wR(F²) = 0.163	H-atom parameters constrained
S = 1.06	Δρ_max = 0.38 e Å⁻³
3340 reflections	Δρ_min = −0.78 e Å⁻³
202 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 > 2sigma(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	0.52570 (18)	0.7545 (4)	1.04046 (16)	0.0569 (7)
N1	0.2835 (2)	0.9106 (4)	0.97974 (18)	0.0486 (8)
N2	0.3849 (2)	0.9266 (4)	0.99532 (18)	0.0508 (8)
H2A	0.4104	1.0278	0.9859	0.061*
C1	0.0956 (5)	1.2768 (9)	1.2266 (4)	0.117 (2)
H1A	0.0772	1.3608	1.2611	0.176*
H1B	0.1383	1.1821	1.2601	0.176*
H1C	0.0380	1.2191	1.1876	0.176*
O2	0.0840 (2)	0.3384 (4)	0.67816 (16)	0.0656 (8)
C2	0.0897 (4)	1.5470 (7)	1.1350 (3)	0.091
H2B	0.0705	1.6238	1.1714	0.136*
H2C	0.0323	1.5035	1.0906	0.136*
H2D	0.1294	1.6189	1.1131	0.136*
C3	0.1471 (4)	1.3827 (7)	1.1817 (3)	0.0881 (16)
H3A	0.2057	1.4352	1.2244	0.106*
C4	0.1840 (3)	1.2577 (6)	1.1290 (3)	0.0657 (11)
C5	0.1216 (3)	1.1481 (7)	1.0656 (3)	0.0792 (14)
H5A	0.0549	1.1507	1.0548	0.095*
C6	0.1557 (3)	1.0349 (6)	1.0180 (3)	0.0684 (12)
H6A	0.1116	0.9649	0.9754	0.082*
C7	0.2539 (3)	1.0251 (5)	1.0332 (2)	0.0467 (9)
C8	0.3165 (3)	1.1359 (5)	1.0951 (2)	0.0538 (10)
H8A	0.3831	1.1348	1.1053	0.065*
C9	0.2817 (3)	1.2487 (6)	1.1424 (3)	0.0626 (11)
H9A	0.3257	1.3203	1.1843	0.075*
C10	0.2671 (3)	0.7054 (5)	0.9853 (2)	0.0485 (9)
H10A	0.2251	0.6878	1.0169	0.058*
C11	0.3691 (3)	0.6265 (5)	1.0361 (2)	0.0522 (10)
H11A	0.3780	0.6123	1.0936	0.063*
H11B	0.3792	0.5064	1.0147	0.063*
C12	0.4378 (3)	0.7731 (5)	1.0257 (2)	0.0473 (9)
C13	0.2185 (3)	0.6143 (5)	0.9026 (2)	0.0489 (9)
C14	0.1919 (3)	0.7046 (6)	0.8282 (2)	0.0556 (10)
H14A	0.2044	0.8320	0.8274	0.067*
C15	0.1471 (3)	0.6114 (6)	0.7545 (2)	0.0583 (11)
H15A	0.1289	0.6768	0.7050	0.070*
C16	0.1289 (3)	0.4205 (6)	0.7537 (2)	0.0544 (10)
C17	0.1560 (3)	0.3291 (6)	0.8282 (2)	0.0691 (12)
H17A	0.1439	0.2017	0.8292	0.083*
C18	0.2002 (3)	0.4224 (5)	0.9003 (2)	0.0636 (12)
H18A	0.2188	0.3565	0.9497	0.076*
C19	0.0726 (3)	0.1427 (6)	0.6765 (3)	0.0721 (13)
H19A	0.0399	0.1019	0.6206	0.108*
H19B	0.0344	0.1084	0.7083	0.108*
H19C	0.1358	0.0845	0.6996	0.108*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0495 (16)	0.0490 (16)	0.0681 (17)	0.0004 (13)	0.0174 (13)	0.0023 (13)
N1	0.0495 (18)	0.0428 (17)	0.0569 (19)	−0.0016 (15)	0.0238 (15)	0.0036 (15)
N2	0.0493 (18)	0.0411 (17)	0.068 (2)	−0.0024 (15)	0.0287 (16)	0.0015 (16)
C1	0.158 (6)	0.112 (5)	0.131 (5)	0.002 (4)	0.110 (5)	−0.012 (4)
O2	0.0709 (19)	0.0627 (19)	0.0500 (16)	−0.0031 (15)	0.0077 (14)	−0.0046 (14)
C2	0.091	0.091	0.091	0.000	0.034	0.000
C3	0.098 (4)	0.083 (4)	0.105 (4)	0.008 (3)	0.064 (3)	−0.003 (3)
C4	0.071 (3)	0.059 (3)	0.078 (3)	−0.003 (2)	0.042 (2)	−0.006 (2)
C5	0.051 (2)	0.092 (4)	0.105 (4)	0.001 (3)	0.040 (3)	−0.009 (3)
C6	0.054 (2)	0.068 (3)	0.089 (3)	−0.016 (2)	0.034 (2)	−0.020 (3)
C7	0.047 (2)	0.042 (2)	0.053 (2)	−0.0051 (17)	0.0211 (18)	−0.0005 (18)
C8	0.051 (2)	0.055 (2)	0.055 (2)	−0.0008 (19)	0.0204 (19)	0.011 (2)
C9	0.074 (3)	0.057 (3)	0.061 (3)	−0.007 (2)	0.029 (2)	−0.008 (2)
C10	0.051 (2)	0.044 (2)	0.055 (2)	−0.0040 (18)	0.0254 (18)	−0.0009 (18)
C11	0.063 (2)	0.041 (2)	0.046 (2)	−0.0069 (19)	0.0129 (18)	−0.0012 (17)
C12	0.056 (2)	0.044 (2)	0.042 (2)	−0.0043 (19)	0.0191 (17)	−0.0029 (17)
C13	0.047 (2)	0.045 (2)	0.050 (2)	−0.0016 (18)	0.0125 (17)	0.0050 (18)
C14	0.057 (2)	0.045 (2)	0.058 (2)	−0.0012 (19)	0.014 (2)	0.0083 (19)
C15	0.065 (3)	0.056 (3)	0.046 (2)	0.001 (2)	0.0116 (19)	0.008 (2)
C16	0.045 (2)	0.061 (3)	0.049 (2)	−0.0008 (19)	0.0084 (17)	0.000 (2)
C17	0.089 (3)	0.046 (2)	0.057 (3)	−0.012 (2)	0.010 (2)	0.001 (2)
C18	0.090 (3)	0.042 (2)	0.049 (2)	−0.008 (2)	0.014 (2)	0.0026 (19)
C19	0.075 (3)	0.069 (3)	0.067 (3)	−0.017 (3)	0.020 (2)	−0.017 (2)

Geometric parameters (Å, º) top

O1—C12	1.229 (4)	C7—C8	1.379 (5)
N1—N2	1.418 (4)	C8—C9	1.383 (5)
N1—C7	1.429 (4)	C8—H8A	0.9300
N1—C10	1.496 (4)	C9—H9A	0.9300
N2—C12	1.336 (4)	C10—C13	1.501 (5)
N2—H2A	0.8600	C10—C11	1.538 (5)
C1—C3	1.488 (6)	C10—H10A	0.9800
C1—H1A	0.9600	C11—C12	1.515 (5)
C1—H1B	0.9600	C11—H11A	0.9700
C1—H1C	0.9600	C11—H11B	0.9700
O2—C16	1.368 (4)	C13—C14	1.372 (5)
O2—C19	1.407 (5)	C13—C18	1.396 (5)
C2—C3	1.498 (6)	C14—C15	1.380 (5)
C2—H2B	0.9600	C14—H14A	0.9300
C2—H2C	0.9600	C15—C16	1.390 (5)
C2—H2D	0.9600	C15—H15A	0.9300
C3—C4	1.524 (6)	C16—C17	1.378 (5)
C3—H3A	0.9800	C17—C18	1.358 (5)
C4—C9	1.370 (5)	C17—H17A	0.9300
C4—C5	1.386 (6)	C18—H18A	0.9300
C5—C6	1.384 (6)	C19—H19A	0.9600
C5—H5A	0.9300	C19—H19B	0.9600
C6—C7	1.372 (5)	C19—H19C	0.9600
C6—H6A	0.9300

N2—N1—C7	112.7 (3)	C4—C9—H9A	119.1
N2—N1—C10	104.5 (3)	C8—C9—H9A	119.1
C7—N1—C10	115.0 (3)	N1—C10—C13	113.1 (3)
C12—N2—N1	115.2 (3)	N1—C10—C11	104.5 (3)
C12—N2—H2A	122.4	C13—C10—C11	114.0 (3)
N1—N2—H2A	122.4	N1—C10—H10A	108.3
C3—C1—H1A	109.5	C13—C10—H10A	108.3
C3—C1—H1B	109.5	C11—C10—H10A	108.3
H1A—C1—H1B	109.5	C12—C11—C10	103.3 (3)
C3—C1—H1C	109.5	C12—C11—H11A	111.1
H1A—C1—H1C	109.5	C10—C11—H11A	111.1
H1B—C1—H1C	109.5	C12—C11—H11B	111.1
C16—O2—C19	117.2 (3)	C10—C11—H11B	111.1
C3—C2—H2B	109.5	H11A—C11—H11B	109.1
C3—C2—H2C	109.5	O1—C12—N2	125.8 (3)
H2B—C2—H2C	109.5	O1—C12—C11	126.8 (3)
C3—C2—H2D	109.5	N2—C12—C11	107.4 (3)
H2B—C2—H2D	109.5	C14—C13—C18	116.9 (4)
H2C—C2—H2D	109.5	C14—C13—C10	125.0 (3)
C1—C3—C2	113.1 (4)	C18—C13—C10	118.1 (3)
C1—C3—C4	112.9 (4)	C13—C14—C15	121.7 (4)
C2—C3—C4	112.7 (4)	C13—C14—H14A	119.1
C1—C3—H3A	105.8	C15—C14—H14A	119.1
C2—C3—H3A	105.8	C14—C15—C16	120.4 (4)
C4—C3—H3A	105.8	C14—C15—H15A	119.8
C9—C4—C5	116.7 (4)	C16—C15—H15A	119.8
C9—C4—C3	121.0 (4)	O2—C16—C17	125.1 (4)
C5—C4—C3	122.4 (4)	O2—C16—C15	116.9 (4)
C6—C5—C4	122.0 (4)	C17—C16—C15	118.0 (4)
C6—C5—H5A	119.0	C18—C17—C16	121.0 (4)
C4—C5—H5A	119.0	C18—C17—H17A	119.5
C7—C6—C5	120.5 (4)	C16—C17—H17A	119.5
C7—C6—H6A	119.8	C17—C18—C13	122.0 (4)
C5—C6—H6A	119.8	C17—C18—H18A	119.0
C6—C7—C8	118.0 (4)	C13—C18—H18A	119.0
C6—C7—N1	117.5 (3)	O2—C19—H19A	109.5
C8—C7—N1	124.4 (3)	O2—C19—H19B	109.5
C7—C8—C9	121.0 (4)	H19A—C19—H19B	109.5
C7—C8—H8A	119.5	O2—C19—H19C	109.5
C9—C8—H8A	119.5	H19A—C19—H19C	109.5
C4—C9—C8	121.7 (4)	H19B—C19—H19C	109.5

C7—N1—N2—C12	112.7 (3)	C7—N1—C10—C11	−103.1 (3)
C10—N1—N2—C12	−12.9 (4)	N1—C10—C11—C12	−21.7 (4)
C1—C3—C4—C9	−120.1 (5)	C13—C10—C11—C12	102.3 (3)
C2—C3—C4—C9	110.2 (5)	N1—N2—C12—O1	176.9 (3)
C1—C3—C4—C5	59.8 (7)	N1—N2—C12—C11	−1.5 (4)
C2—C3—C4—C5	−69.8 (6)	C10—C11—C12—O1	−163.7 (4)
C9—C4—C5—C6	0.0 (7)	C10—C11—C12—N2	14.7 (4)
C3—C4—C5—C6	−180.0 (4)	N1—C10—C13—C14	0.7 (5)
C4—C5—C6—C7	1.2 (8)	C11—C10—C13—C14	−118.5 (4)
C5—C6—C7—C8	−2.2 (6)	N1—C10—C13—C18	179.5 (4)
C5—C6—C7—N1	−177.8 (4)	C11—C10—C13—C18	60.3 (5)
N2—N1—C7—C6	173.6 (3)	C18—C13—C14—C15	1.4 (6)
C10—N1—C7—C6	−66.8 (5)	C10—C13—C14—C15	−179.8 (4)
N2—N1—C7—C8	−1.8 (5)	C13—C14—C15—C16	−1.0 (6)
C10—N1—C7—C8	117.9 (4)	C19—O2—C16—C17	−5.9 (6)
C6—C7—C8—C9	2.1 (6)	C19—O2—C16—C15	174.9 (4)
N1—C7—C8—C9	177.4 (4)	C14—C15—C16—O2	179.8 (3)
C5—C4—C9—C8	0.0 (7)	C14—C15—C16—C17	0.6 (6)
C3—C4—C9—C8	179.9 (4)	O2—C16—C17—C18	−179.9 (4)
C7—C8—C9—C4	−1.1 (6)	C15—C16—C17—C18	−0.7 (7)
N2—N1—C10—C13	−103.6 (3)	C16—C17—C18—C13	1.2 (7)
C7—N1—C10—C13	132.3 (3)	C14—C13—C18—C17	−1.5 (7)
N2—N1—C10—C11	21.0 (4)	C10—C13—C18—C17	179.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	1.96	2.819 (4)	175
C8—H8A···N2	0.93	2.44	2.761 (5)	100
C14—H14A···N1	0.93	2.54	2.887 (5)	102

Symmetry code: (i) −x+1, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₂N₂O₂
M_r	310.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	14.737 (3), 7.1490 (14), 17.493 (4)
β (°)	112.03 (3)
V (Å³)	1708.4 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.969, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	3472, 3340, 1835
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.163, 1.06
No. of reflections	3340
No. of parameters	202
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.78

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	1.96	2.819 (4)	175.0
C8—H8A···N2	0.93	2.44	2.761 (5)	100.0
C14—H14A···N1	0.93	2.54	2.887 (5)	102.0

Symmetry code: (i) −x+1, −y+2, −z+2.

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

Brooks, D. W., Basha, A., Gunn, B. P. & Bhatia, P. A. (1990). US Patent No. 4 970 210. Google Scholar
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Greenwood, B., Helton, D. R. & Howbert, J. J. (1995). US Patent No. 5 399 565. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
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North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
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Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar