1-Phenyl-5-[4-(trifluoro-meth-yl)phen-yl]-pyrazolidin-3-one monohydrate.

In the mol-ecule of the title compound, C(16)H(13)F(3)N(2)O·H(2)O, 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, inter-molecular C-H⋯F hydrogen bonds link the mol-ecules 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·n class="Chemical">H2O

M = 324.30

Triclinic,

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[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.186

S = 1.00

3196 reflections

211 parameters

48 restraints

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.23 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H13F3N2O·H2O	Z = 2
Mr = 324.30	F(000) = 336
Triclinic, P1	Dx = 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

Enraf–Nonius CAD-4 diffractometer	1611 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.068
graphite	θmax = 25.2°, θmin = 1.6°
ω/2θ scans	h = −8→8
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
Tmin = 0.980, Tmax = 0.995	l = 0→15
3463 measured reflections	3 standard reflections every 120 min
3196 independent reflections	intensity decay: none

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(Fo2) + (0.06P)2 + 0.58P] where P = (Fo2 + 2Fc2)/3
3196 reflections	(Δ/σ)max < 0.001
211 parameters	Δρmax = 0.21 e Å−3
48 restraints	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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)

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

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) ; (ii) ; (iii) .