1-Phenyl-5-[4-(trifluoro­meth­yl)phen­yl]­pyrazolidin-3-one monohydrate

Liu, Y.-Y.; Wu, Z.-Y.; Shi, H.; Chu, Q.-Y.; Zhu, H.-J.

doi:10.1107/S1600536808032261

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2101

doi:10.1107/S1600536808032261

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1-Phenyl-5-[4-(trifluoromethyl)phenyl]pyrazolidin-3-one monohydrate

Yuan-Yuan Liu,^a Zhen-Yi Wu,^a Hong Shi,^a Qing-Yan Chu ^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 26 August 2008; accepted 7 October 2008; online 11 October 2008)

In the molecule of the title compound, C₁₆H₁₃F₃N₂O·H₂O, the two benzene rings are oriented at a dihedral angle of 82.55 (3)° and the pyrazole ring adopts an envelope conformation. In the crystal structure, intermolecular C—H⋯F hydrogen bonds link the molecules into chains.

Related literature

For general background, see: Menozzi et al. (1990 ); James & William (2003 ); Shi et al. (2006 ). For related literature, see: Jia et al. (2008 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₃F₃N₂O·H₂O
M_r = 324.30
Triclinic, $[P \overline 1]$
a = 7.4960 (15) Å
b = 9.794 (2) Å
c = 13.319 (3) Å
α = 97.70 (3)°
β = 101.58 (3)°
γ = 107.97 (3)°
V = 890.8 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 294 (2) K
0.20 × 0.10 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.980, T_max = 0.995
3463 measured reflections
3196 independent reflections
1611 reflections with I > 2σ(I)
R_int = 0.068
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.077
wR(F²) = 0.186
S = 1.00
3196 reflections
211 parameters
48 restraints
H-atom parameters constrained
Δρ_max = 0.21 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
OW2—HW2B⋯OW1	0.85	1.99	2.50 (3)	118
C14—H14A⋯F3ⁱ	0.93	2.54	3.262 (6)	134
N1—H1A⋯Oⁱⁱ	0.86	1.98	2.811 (6)	161
C9—H9B⋯Oⁱⁱⁱ	0.97	2.60	3.555 (7)	168
Symmetry code: (i) x-1, y+1, z; (ii) -x+1, -y+2, -z+2; (iii) -x+2, -y+2, -z+2.

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); 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); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808032261/hk2518sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808032261/hk2518Isup2.hkl

checkCIF report

Comment top

Nowadays, heterocyclic compounds as medicines and pesticides have been developed most quickly. Among them, pyrazole and its derivatives exhibit better bioactivity, such as antipyretic (Menozzi et al., 1990) and anticancer (James & William, 2003) activities. They are also useful in the treatment of inflammation and related disorders (Shi et al., 2006). We report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C2-C7) and C (C11-C16) are, of course, planar and the dihedral angle between them is 82.55 (3)°. Ring B (N1/N2/C8-C10) is not planar, and adopts envelope conformation with C8 atom displaced by 0.358 (3) Å from the plane of the other ring atoms. The intramolecular C-H···N and C-H···F hydrogen bonds (Table 1) result in the formation of two planar five-membered rings D (N2/C4/C5/C8/H4A) and E (F3/C1/C2/C7/H7A). They are oriented with respect to ring A at dihedral angles of 3.20 (3)° and 2.57 (3)°, respectively. So, rings A, D and E are nearly coplanar.

In the crystal structure, intermolecular C-H···F hydrogen bonds (Table 1) link the molecules into chains (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); James & William (2003); Shi et al. (2006). For related literature, see: Jia et al. (2008). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by the literature method (Jia et al., 2008). For the preparation of the title compound, n-butanol (40 ml) and ethanolamine (4 ml) were added to a solution of sodium (40 mmol) in anhydrous methanol (9 ml). Then, methanol was removed by distillation and methyl 3-(4-(trifluoromethyl)phenyl)acrylate (30 mmol) was added. The mixture was refluxed for 1.5 h at 385 K, after which phenylhydrazine (4 ml) was added. The mixture was refluxed for another 10 h, and then left to cool to room temperature. It was then acidified with acetic acid (50%), allowed to stand and filtered. The filter cake was chromatographed over silica gel (500 g) eluting with a mixture of ethyl acetate and petroleum ether to give the title compound (m.p. 413- 415 K). Crystals suitable for x-ray analysis were obtained by dissolving the title compound (1.5 g) in ethyl acetate (25 ml) and evaporating the solvent slowly at room temperature for about 10 d.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); 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); 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 50% probability level. Hydrogen bonds are shown as dotted lines.
	Fig. 2. A packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

1-Phenyl-5-[4-(trifluoromethyl)phenyl]pyrazolidin-3-one monohydrate top

Crystal data top

C₁₆H₁₃F₃N₂O·H₂O	Z = 2
M_r = 324.30	F(000) = 336
Triclinic, P1	D_x = 1.209 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4960 (15) Å	Cell parameters from 25 reflections
b = 9.794 (2) Å	θ = 9–12°
c = 13.319 (3) Å	µ = 0.10 mm⁻¹
α = 97.70 (3)°	T = 294 K
β = 101.58 (3)°	Needle, colorless
γ = 107.97 (3)°	0.20 × 0.10 × 0.05 mm
V = 890.8 (4) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	1611 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.068
Graphite monochromator	θ_max = 25.2°, θ_min = 1.6°
ω/2θ scans	h = −8→8
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
T_min = 0.980, T_max = 0.995	l = 0→15
3463 measured reflections	3 standard reflections every 120 min
3196 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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.186	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.06P)² + 0.58P] where P = (F_o² + 2F_c²)/3
3196 reflections	(Δ/σ)_max < 0.001
211 parameters	Δρ_max = 0.21 e Å⁻³
48 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₆H₁₃F₃N₂O·H₂O	γ = 107.97 (3)°
M_r = 324.30	V = 890.8 (4) Å³
Triclinic, P1	Z = 2
a = 7.4960 (15) Å	Mo Kα radiation
b = 9.794 (2) Å	µ = 0.10 mm⁻¹
c = 13.319 (3) Å	T = 294 K
α = 97.70 (3)°	0.20 × 0.10 × 0.05 mm
β = 101.58 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1611 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.068
T_min = 0.980, T_max = 0.995	3 standard reflections every 120 min
3463 measured reflections	intensity decay: none
3196 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.077	48 restraints
wR(F²) = 0.186	H-atom parameters constrained
S = 1.00	Δρ_max = 0.21 e Å⁻³
3196 reflections	Δρ_min = −0.23 e Å⁻³
211 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	Occ. (<1)
OW1	0.464 (3)	1.4138 (15)	1.0235 (11)	0.288 (8)	0.50
HW1A	0.5305	1.3813	1.0675	0.345*	0.50
HW1B	0.4367	1.4891	1.0439	0.345*	0.50
OW2	0.805 (3)	1.5022 (19)	1.0058 (13)	0.328 (9)	0.50
HW2A	0.8673	1.5642	0.9752	0.394*	0.50
HW2B	0.7436	1.5280	1.0477	0.394*	0.50
O	0.7711 (4)	1.0639 (3)	1.0297 (2)	0.0741 (9)
N1	0.5378 (4)	0.9682 (3)	0.8750 (2)	0.0520 (8)
H1A	0.4422	0.9388	0.9027	0.062*
N2	0.5122 (4)	0.9482 (3)	0.7661 (2)	0.0495 (7)
F1	0.8128 (5)	0.3357 (4)	0.6898 (3)	0.1429 (12)
F2	0.7729 (6)	0.3635 (4)	0.5389 (3)	0.1549 (14)
F3	1.0292 (5)	0.4452 (4)	0.6316 (3)	0.1343 (11)
C1	0.8642 (9)	0.4424 (7)	0.6409 (5)	0.097
C2	0.8153 (7)	0.5692 (4)	0.6625 (3)	0.0695 (11)
C3	0.6372 (7)	0.5629 (5)	0.6753 (4)	0.0924 (15)
H3A	0.5419	0.4721	0.6676	0.111*
C4	0.5972 (6)	0.6888 (5)	0.6994 (4)	0.0869 (14)
H4A	0.4717	0.6827	0.7014	0.104*
C5	0.7395 (5)	0.8228 (4)	0.7207 (3)	0.0480 (9)
C6	0.9191 (5)	0.8233 (4)	0.7059 (3)	0.0654 (11)
H6A	1.0176	0.9128	0.7150	0.079*
C7	0.9539 (6)	0.6985 (5)	0.6791 (3)	0.0660 (11)
H7A	1.0764	0.7030	0.6721	0.079*
C8	0.7150 (4)	0.9668 (4)	0.7541 (2)	0.0443 (8)
H8A	0.7384	1.0243	0.7003	0.053*
C9	0.8485 (5)	1.0570 (4)	0.8573 (2)	0.0512 (9)
H9A	0.9001	1.1596	0.8538	0.061*
H9B	0.9556	1.0222	0.8777	0.061*
C10	0.7225 (5)	1.0368 (4)	0.9337 (3)	0.0568 (10)
C11	0.4190 (4)	1.0326 (4)	0.7171 (3)	0.0485 (9)
C12	0.3624 (5)	1.0040 (4)	0.6080 (3)	0.0587 (10)
H12A	0.3921	0.9310	0.5698	0.070*
C13	0.2660 (6)	1.0793 (5)	0.5571 (3)	0.0694 (12)
H13A	0.2318	1.0592	0.4842	0.083*
C14	0.2170 (6)	1.1866 (5)	0.6116 (4)	0.0759 (12)
H14A	0.1510	1.2393	0.5760	0.091*
C15	0.2666 (6)	1.2142 (4)	0.7181 (4)	0.0716 (12)
H15A	0.2292	1.2840	0.7545	0.086*
C16	0.3695 (5)	1.1430 (4)	0.7737 (3)	0.0557 (10)
H16A	0.4060	1.1662	0.8466	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
OW1	0.37 (2)	0.239 (16)	0.249 (16)	0.119 (17)	0.069 (15)	0.038 (12)
OW2	0.31 (2)	0.312 (19)	0.33 (2)	0.089 (17)	0.053 (17)	0.039 (15)
O	0.0489 (17)	0.132 (3)	0.0524 (17)	0.0415 (16)	0.0149 (13)	0.0292 (16)
N1	0.0365 (17)	0.082 (2)	0.0465 (17)	0.0262 (16)	0.0146 (14)	0.0257 (15)
N2	0.0361 (16)	0.0695 (19)	0.0517 (18)	0.0246 (15)	0.0166 (14)	0.0191 (15)
F1	0.161 (3)	0.128 (3)	0.146 (3)	0.051 (2)	0.048 (3)	0.037 (2)
F2	0.168 (4)	0.152 (3)	0.143 (3)	0.061 (3)	0.033 (3)	0.020 (2)
F3	0.134 (3)	0.131 (3)	0.149 (3)	0.054 (2)	0.046 (2)	0.030 (2)
C1	0.106	0.099	0.095	0.045	0.038	0.010
C2	0.080 (3)	0.060 (2)	0.079 (3)	0.037 (2)	0.025 (2)	0.013 (2)
C3	0.084 (3)	0.070 (3)	0.119 (4)	0.013 (2)	0.043 (3)	0.009 (3)
C4	0.053 (3)	0.076 (3)	0.124 (4)	0.011 (2)	0.037 (3)	0.004 (3)
C5	0.0356 (19)	0.057 (2)	0.056 (2)	0.0196 (17)	0.0133 (16)	0.0184 (17)
C6	0.039 (2)	0.071 (2)	0.083 (3)	0.0130 (19)	0.023 (2)	0.007 (2)
C7	0.053 (2)	0.078 (3)	0.082 (3)	0.036 (2)	0.026 (2)	0.022 (2)
C8	0.0291 (18)	0.068 (2)	0.0437 (19)	0.0187 (17)	0.0230 (15)	0.0132 (17)
C9	0.0347 (19)	0.070 (2)	0.046 (2)	0.0167 (18)	0.0150 (16)	−0.0019 (17)
C10	0.036 (2)	0.087 (3)	0.053 (2)	0.021 (2)	0.0159 (18)	0.026 (2)
C11	0.0298 (19)	0.064 (2)	0.058 (2)	0.0191 (17)	0.0170 (17)	0.0159 (18)
C12	0.054 (2)	0.088 (3)	0.043 (2)	0.040 (2)	0.0123 (18)	0.0052 (19)
C13	0.069 (3)	0.110 (3)	0.040 (2)	0.039 (3)	0.018 (2)	0.025 (2)
C14	0.065 (3)	0.104 (3)	0.074 (3)	0.043 (3)	0.019 (2)	0.039 (3)
C15	0.065 (3)	0.069 (3)	0.095 (3)	0.040 (2)	0.029 (2)	0.012 (2)
C16	0.044 (2)	0.072 (2)	0.053 (2)	0.025 (2)	0.0106 (18)	0.0093 (19)

Geometric parameters (Å, º) top

OW1—HW1A	0.8502	C5—C8	1.499 (4)
OW1—HW1B	0.8499	C6—C7	1.344 (5)
OW2—HW2A	0.8500	C6—H6A	0.9300
OW2—HW2B	0.8499	C7—H7A	0.9300
O—C10	1.226 (4)	C8—C9	1.499 (4)
N1—C10	1.352 (4)	C8—H8A	0.9800
N1—N2	1.404 (4)	C9—C10	1.513 (4)
N1—H1A	0.8600	C9—H9A	0.9700
N2—C11	1.384 (4)	C9—H9B	0.9700
N2—C8	1.518 (4)	C11—C12	1.392 (5)
F1—C1	1.303 (6)	C11—C16	1.420 (5)
F2—C1	1.389 (6)	C12—C13	1.339 (5)
F3—C1	1.260 (6)	C12—H12A	0.9300
C1—C2	1.409 (6)	C13—C14	1.381 (5)
C2—C7	1.324 (5)	C13—H13A	0.9300
C2—C3	1.363 (6)	C14—C15	1.358 (5)
C3—C4	1.369 (6)	C14—H14A	0.9300
C3—H3A	0.9300	C15—C16	1.368 (5)
C4—C5	1.363 (5)	C15—H15A	0.9300
C4—H4A	0.9300	C16—H16A	0.9300
C5—C6	1.398 (4)

HW1A—OW1—HW1B	120.0	C5—C8—N2	112.4 (3)
HW2A—OW2—HW2B	120.0	C9—C8—N2	105.1 (2)
C10—N1—N2	115.7 (3)	C5—C8—H8A	108.2
C10—N1—H1A	122.2	C9—C8—H8A	108.2
N2—N1—H1A	122.2	N2—C8—H8A	108.2
C11—N2—N1	115.6 (3)	C8—C9—C10	104.5 (3)
C11—N2—C8	116.8 (3)	C8—C9—H9A	110.9
N1—N2—C8	102.8 (2)	C10—C9—H9A	110.9
F3—C1—F1	103.2 (5)	C8—C9—H9B	110.9
F3—C1—F2	92.8 (4)	C10—C9—H9B	110.9
F1—C1—F2	98.4 (5)	H9A—C9—H9B	108.9
F3—C1—C2	123.8 (6)	O—C10—N1	124.4 (3)
F1—C1—C2	120.7 (5)	O—C10—C9	129.1 (3)
F2—C1—C2	111.8 (5)	N1—C10—C9	106.2 (3)
C7—C2—C3	119.5 (4)	N2—C11—C12	119.1 (3)
C7—C2—C1	117.8 (5)	N2—C11—C16	122.5 (3)
C3—C2—C1	122.4 (5)	C12—C11—C16	118.3 (3)
C2—C3—C4	120.7 (4)	C13—C12—C11	121.3 (3)
C2—C3—H3A	119.7	C13—C12—H12A	119.3
C4—C3—H3A	119.7	C11—C12—H12A	119.3
C5—C4—C3	120.7 (4)	C12—C13—C14	120.7 (4)
C5—C4—H4A	119.7	C12—C13—H13A	119.6
C3—C4—H4A	119.7	C14—C13—H13A	119.6
C4—C5—C6	116.1 (4)	C15—C14—C13	119.0 (4)
C4—C5—C8	125.2 (3)	C15—C14—H14A	120.5
C6—C5—C8	118.7 (3)	C13—C14—H14A	120.5
C7—C6—C5	122.1 (4)	C14—C15—C16	122.4 (4)
C7—C6—H6A	118.9	C14—C15—H15A	118.8
C5—C6—H6A	118.9	C16—C15—H15A	118.8
C2—C7—C6	120.6 (4)	C15—C16—C11	118.1 (3)
C2—C7—H7A	119.7	C15—C16—H16A	120.9
C6—C7—H7A	119.7	C11—C16—H16A	120.9
C5—C8—C9	114.7 (3)

C10—N1—N2—C11	−109.8 (3)	C11—N2—C8—C5	−130.5 (3)
C10—N1—N2—C8	18.6 (4)	N1—N2—C8—C5	101.8 (3)
F3—C1—C2—C7	−3.6 (8)	C11—N2—C8—C9	104.2 (3)
F1—C1—C2—C7	132.2 (6)	N1—N2—C8—C9	−23.5 (3)
F2—C1—C2—C7	−112.9 (5)	C5—C8—C9—C10	−103.1 (3)
F3—C1—C2—C3	−178.0 (5)	N2—C8—C9—C10	20.8 (4)
F1—C1—C2—C3	−42.2 (8)	N2—N1—C10—O	179.7 (3)
F2—C1—C2—C3	72.7 (7)	N2—N1—C10—C9	−5.5 (4)
C7—C2—C3—C4	3.6 (7)	C8—C9—C10—O	164.2 (4)
C1—C2—C3—C4	177.9 (5)	C8—C9—C10—N1	−10.4 (4)
C2—C3—C4—C5	−6.1 (7)	N1—N2—C11—C12	−170.6 (3)
C3—C4—C5—C6	6.2 (6)	C8—N2—C11—C12	68.2 (4)
C3—C4—C5—C8	−176.1 (4)	N1—N2—C11—C16	6.1 (5)
C4—C5—C6—C7	−4.2 (6)	C8—N2—C11—C16	−115.1 (3)
C8—C5—C6—C7	177.9 (3)	N2—C11—C12—C13	177.7 (4)
C3—C2—C7—C6	−1.6 (7)	C16—C11—C12—C13	0.9 (6)
C1—C2—C7—C6	−176.2 (4)	C11—C12—C13—C14	−1.1 (6)
C5—C6—C7—C2	2.0 (6)	C12—C13—C14—C15	−0.5 (6)
C4—C5—C8—C9	121.9 (4)	C13—C14—C15—C16	2.3 (7)
C6—C5—C8—C9	−60.5 (4)	C14—C15—C16—C11	−2.4 (6)
C4—C5—C8—N2	2.0 (5)	N2—C11—C16—C15	−175.9 (3)
C6—C5—C8—N2	179.6 (3)	C12—C11—C16—C15	0.8 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
OW2—HW2B···OW1	0.85	1.99	2.50 (3)	118
C4—H4A···N2	0.93	2.53	2.875 (6)	102
C7—H7A···F3	0.93	2.41	2.731 (6)	100
C14—H14A···F3ⁱ	0.93	2.54	3.262 (6)	134
N1—H1A···Oⁱⁱ	0.86	1.98	2.811 (6)	161
C9—H9B···Oⁱⁱⁱ	0.97	2.60	3.555 (7)	168

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃F₃N₂O·H₂O
M_r	324.30
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	7.4960 (15), 9.794 (2), 13.319 (3)
α, β, γ (°)	97.70 (3), 101.58 (3), 107.97 (3)
V (Å³)	890.8 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.10 × 0.05

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.980, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	3463, 3196, 1611
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.077, 0.186, 1.00
No. of reflections	3196
No. of parameters	211
No. of restraints	48
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.23

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), 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
OW2—HW2B···OW1	0.85	1.99	2.50 (3)	118.00
C14—H14A···F3ⁱ	0.93	2.54	3.262 (6)	134.00
N1—H1A···Oⁱⁱ	0.86	1.98	2.811 (6)	161
C9—H9B···Oⁱⁱⁱ	0.97	2.60	3.555 (7)	168

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

Acknowledgements

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

References

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