(2Z)-3-(4-Fluoro­anilino)-1-(5-hy­droxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)but-2-en-1-one

Asiri, A.M.; Faidallah, H.M.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812006514

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o764

doi:10.1107/S1600536812006514

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(2Z)-3-(4-Fluoroanilino)-1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)but-2-en-1-one

Abdullah M. Asiri,^a,^b ‡ Hassan M. Faidallah,^a Seik Weng Ng ^c and Edward R. T. Tiekink ^c ^*

^aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia, ^bThe Center of Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah, PO Box 80203, Saudi Arabia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 12 February 2012; accepted 14 February 2012; online 17 February 2012)

The central carbonyl group in the title compound, C₂₀H₁₈FN₃O₂, forms amine–hydroxy N—H⋯O and hydroxy–hydroxy O—H⋯O hydrogen bonds, leading to two S(6) rings. The N-bound phenyl ring is coplanar with the five-membered ring to which it is attached [dihedral angle = 6.27 (10)°], but an overall twist in the molecule is evident, the dihedral angle between the terminal phenyl and benzene rings being 27.30 (10)°. Molecules aggregate into a three-dimensional architecture via C—H⋯F, C—H⋯O and C—H⋯π interactions.

Related literature

For background to the synthesis, see: Gelin et al. (1983 ); Bendaas et al. (1999 ). For the structures of the 4-chloro and 4-methoxy derivatives, see: Asiri, Al-Youbi, Alamry et al. (2011 ); Asiri, Al-Youbi, Faidallah et al. (2011 ).

Experimental

Crystal data

C₂₀H₁₈FN₃O₂
M_r = 351.37
Monoclinic, P 2₁ /c
a = 8.3871 (7) Å
b = 11.1368 (9) Å
c = 18.4772 (16) Å
β = 101.317 (8)°
V = 1692.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.20 × 0.05 × 0.02 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.981, T_max = 0.998
7099 measured reflections
3866 independent reflections
2504 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.123
S = 1.05
3866 reflections
245 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C15–C20 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.86 (1)	1.73 (2)	2.521 (2)	152 (3)
N3—H3⋯O2	0.88 (1)	1.95 (2)	2.686 (2)	139 (2)
C14—H14A⋯F1ⁱ	0.98	2.43	3.309 (3)	150
C19—H19⋯O2ⁱⁱ	0.95	2.55	3.410 (3)	150
C16—H16⋯Cg1ⁱⁱⁱ	0.95	2.59	3.496 (3)	161
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812006514/hg5178sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006514/hg5178Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812006514/hg5178Isup3.cml

checkCIF report

Comment top

During recent investigations of reactions between pyrazoles and aniline derivatives based on literature precedents (Gelin et al., 1983; Bendaas et al., 1999), several compounds were isolated in crystalline form and some structures determined (Asiri, Al-Youbi, Alamry et al., 2011; Asiri, Al-Youbi, Faidallah et al., 2011). As a continuation of these studies, the title compound 3-(4-fluoroanilino)-1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)but-2-en-1-one (I) was investigated.

In (I), Fig. 1, the central O2-carbonyl atom accepts two hydrogen bonds from the adjacent hydroxyl and amine groups to close a pair of fused S(6) rings, Table 1. The N-bound phenyl ring is co-planar with the five-membered ring forming a dihedral angle of 6.27 (10)°. By contrast, the fluorobenzene ring is twisted out of the plane of the rest of the molecule as seen in the value of the C13—N3—C15—C16 torsion angle of -149.5 (2)°; the dihedral angle between the terminal phenyl and benzene rings is 27.30 (10)°.

Molecules aggregate into the three-dimensional architecture via C—H···F, C—H···O and C—H···π interactions, Fig. 2 and Table 1.

Related literature top

For background to the synthesis, see: Gelin et al. (1983); Bendaas et al. (1999). For the structures of the 4-chloro and 4-methoxy derivatives, see: Asiri, Al-Youbi, Alamry et al. (2011); Asiri, Al-Youbi, Faidallah et al. (2011).

Experimental top

A solution of 4-acetoacetyl-5-hydroxy-3-methyl-1 phenylpyrazole (0.005 mol) and 4-fluoroaniline (0.005 mol) in ethanol (25 ml) was refluxed for 2 h. The precipitate, obtained from the hot solution, was collected, washed with methanol and recrystallized from was from its ethanol-benzene solution. Orange plates were harvested; M.pt: 443–445 K.

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: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view in projection down the a axis of the unit-cell contents of (I). The C—H···F, C—H···O and C—H···π interactions are shown as blue, orange and purple dashed lines, respectively.

(2Z)-3-(4-Fluoroanilino)-1-(5-hydroxy-3-methyl-1-phenyl-1H- pyrazol-4-yl)but-2-en-1-one top

Crystal data top

C₂₀H₁₈FN₃O₂	F(000) = 736
M_r = 351.37	D_x = 1.379 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1871 reflections
a = 8.3871 (7) Å	θ = 2.5–27.5°
b = 11.1368 (9) Å	µ = 0.10 mm⁻¹
c = 18.4772 (16) Å	T = 100 K
β = 101.317 (8)°	Plate, orange
V = 1692.3 (2) Å³	0.20 × 0.05 × 0.02 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3866 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2504 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.038
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.5°
ω scan	h = −7→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −10→14
T_min = 0.981, T_max = 0.998	l = −22→24
7099 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0355P)²] where P = (F_o² + 2F_c²)/3
3866 reflections	(Δ/σ)_max = 0.001
245 parameters	Δρ_max = 0.25 e Å⁻³
2 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₀H₁₈FN₃O₂	V = 1692.3 (2) Å³
M_r = 351.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.3871 (7) Å	µ = 0.10 mm⁻¹
b = 11.1368 (9) Å	T = 100 K
c = 18.4772 (16) Å	0.20 × 0.05 × 0.02 mm
β = 101.317 (8)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3866 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2504 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.998	R_int = 0.038
7099 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	2 restraints
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.25 e Å⁻³
3866 reflections	Δρ_min = −0.29 e Å⁻³
245 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F1	0.00255 (17)	0.62060 (12)	0.97089 (8)	0.0409 (4)
O1	0.41629 (18)	0.25671 (13)	0.53785 (8)	0.0231 (4)
H1	0.375 (3)	0.286 (2)	0.5730 (12)	0.069 (10)*
O2	0.27537 (17)	0.39755 (12)	0.61177 (8)	0.0224 (4)
N1	0.40945 (19)	0.33193 (15)	0.41680 (9)	0.0182 (4)
N2	0.34816 (19)	0.43289 (15)	0.37538 (10)	0.0196 (4)
N3	0.1370 (2)	0.55252 (16)	0.69228 (10)	0.0203 (4)
H3	0.193 (2)	0.4868 (13)	0.6878 (13)	0.036 (7)*
C1	0.4836 (2)	0.23985 (18)	0.38159 (12)	0.0180 (5)
C2	0.5548 (2)	0.13998 (18)	0.42087 (13)	0.0241 (5)
H2	0.5564	0.1330	0.4723	0.029*
C3	0.6234 (3)	0.0508 (2)	0.38406 (13)	0.0277 (5)
H3A	0.6712	−0.0177	0.4105	0.033*
C4	0.6227 (3)	0.0607 (2)	0.30946 (13)	0.0273 (6)
H4	0.6699	−0.0006	0.2847	0.033*
C5	0.5528 (2)	0.1606 (2)	0.27070 (13)	0.0258 (5)
H5	0.5520	0.1674	0.2194	0.031*
C6	0.4842 (2)	0.25036 (19)	0.30655 (12)	0.0231 (5)
H6	0.4376	0.3190	0.2800	0.028*
C7	0.3767 (2)	0.33942 (18)	0.48588 (11)	0.0175 (5)
C8	0.2937 (2)	0.44604 (18)	0.49086 (11)	0.0168 (4)
C9	0.2795 (2)	0.49994 (18)	0.41992 (12)	0.0176 (5)
C10	0.2000 (2)	0.61536 (18)	0.39152 (12)	0.0221 (5)
H10A	0.1995	0.6224	0.3386	0.033*
H10B	0.2606	0.6828	0.4178	0.033*
H10C	0.0880	0.6166	0.3996	0.033*
C11	0.2433 (2)	0.47650 (18)	0.55928 (12)	0.0184 (5)
C12	0.1636 (2)	0.58608 (18)	0.56826 (11)	0.0177 (5)
H12	0.1423	0.6388	0.5271	0.021*
C13	0.1141 (2)	0.62287 (18)	0.63183 (12)	0.0183 (5)
C14	0.0365 (3)	0.74430 (18)	0.63272 (12)	0.0233 (5)
H14A	0.0672	0.7948	0.5942	0.035*
H14B	0.0738	0.7819	0.6810	0.035*
H14C	−0.0820	0.7354	0.6235	0.035*
C15	0.0973 (2)	0.57223 (19)	0.76250 (12)	0.0198 (5)
C16	0.1966 (3)	0.51939 (19)	0.82326 (13)	0.0254 (5)
H16	0.2878	0.4734	0.8164	0.030*
C17	0.1645 (3)	0.5328 (2)	0.89379 (13)	0.0275 (5)
H17	0.2311	0.4954	0.9352	0.033*
C18	0.0323 (3)	0.6024 (2)	0.90176 (13)	0.0265 (5)
C19	−0.0693 (3)	0.6538 (2)	0.84292 (13)	0.0255 (5)
H19	−0.1594	0.7006	0.8503	0.031*
C20	−0.0396 (2)	0.63699 (19)	0.77237 (13)	0.0235 (5)
H20	−0.1120	0.6694	0.7309	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0595 (10)	0.0460 (9)	0.0209 (8)	−0.0049 (7)	0.0172 (7)	−0.0090 (7)
O1	0.0295 (9)	0.0225 (9)	0.0180 (9)	0.0055 (7)	0.0067 (7)	0.0035 (7)
O2	0.0260 (8)	0.0237 (8)	0.0188 (9)	0.0018 (6)	0.0071 (7)	0.0027 (7)
N1	0.0188 (9)	0.0195 (9)	0.0161 (10)	0.0028 (7)	0.0031 (8)	0.0010 (8)
N2	0.0193 (9)	0.0209 (10)	0.0184 (10)	0.0018 (7)	0.0032 (8)	0.0015 (8)
N3	0.0226 (10)	0.0226 (11)	0.0166 (10)	0.0013 (8)	0.0063 (8)	−0.0013 (8)
C1	0.0131 (10)	0.0201 (12)	0.0201 (12)	0.0005 (8)	0.0013 (9)	−0.0046 (9)
C2	0.0253 (11)	0.0242 (12)	0.0224 (13)	0.0029 (10)	0.0039 (10)	−0.0031 (10)
C3	0.0292 (12)	0.0220 (13)	0.0309 (14)	0.0046 (10)	0.0035 (11)	−0.0018 (10)
C4	0.0252 (12)	0.0265 (13)	0.0300 (14)	0.0027 (10)	0.0048 (11)	−0.0121 (11)
C5	0.0204 (11)	0.0334 (14)	0.0233 (13)	0.0007 (10)	0.0036 (10)	−0.0073 (11)
C6	0.0194 (11)	0.0291 (13)	0.0202 (12)	0.0033 (9)	0.0029 (10)	−0.0004 (10)
C7	0.0159 (10)	0.0209 (11)	0.0157 (11)	−0.0022 (9)	0.0027 (9)	0.0018 (9)
C8	0.0133 (9)	0.0215 (11)	0.0157 (11)	−0.0023 (8)	0.0034 (8)	0.0001 (9)
C9	0.0150 (10)	0.0186 (11)	0.0190 (11)	−0.0020 (8)	0.0026 (9)	−0.0019 (9)
C10	0.0248 (11)	0.0213 (11)	0.0209 (12)	0.0011 (9)	0.0063 (10)	0.0005 (9)
C11	0.0139 (10)	0.0228 (12)	0.0176 (11)	−0.0063 (9)	0.0014 (9)	−0.0015 (10)
C12	0.0177 (10)	0.0195 (11)	0.0160 (11)	0.0006 (9)	0.0031 (9)	0.0008 (9)
C13	0.0164 (10)	0.0193 (11)	0.0192 (12)	−0.0044 (9)	0.0033 (9)	−0.0003 (9)
C14	0.0282 (12)	0.0227 (13)	0.0199 (13)	0.0008 (9)	0.0069 (10)	−0.0010 (10)
C15	0.0234 (11)	0.0208 (12)	0.0160 (11)	−0.0033 (9)	0.0062 (9)	−0.0013 (9)
C16	0.0283 (12)	0.0246 (13)	0.0244 (13)	0.0014 (10)	0.0082 (10)	0.0010 (10)
C17	0.0338 (13)	0.0286 (13)	0.0179 (12)	−0.0021 (11)	−0.0005 (10)	0.0035 (10)
C18	0.0391 (13)	0.0268 (13)	0.0160 (12)	−0.0091 (11)	0.0114 (11)	−0.0072 (10)
C19	0.0262 (12)	0.0243 (13)	0.0288 (14)	−0.0030 (10)	0.0126 (11)	−0.0036 (10)
C20	0.0206 (11)	0.0281 (13)	0.0213 (13)	−0.0023 (9)	0.0031 (10)	−0.0010 (10)

Geometric parameters (Å, º) top

F1—C18	1.364 (2)	C8—C9	1.425 (3)
O1—C7	1.325 (2)	C8—C11	1.450 (3)
O1—H1	0.860 (10)	C9—C10	1.495 (3)
O2—C11	1.298 (2)	C10—H10A	0.9800
N1—C7	1.360 (2)	C10—H10B	0.9800
N1—N2	1.400 (2)	C10—H10C	0.9800
N1—C1	1.421 (2)	C11—C12	1.417 (3)
N2—C9	1.324 (2)	C12—C13	1.382 (3)
N3—C13	1.347 (3)	C12—H12	0.9500
N3—C15	1.419 (2)	C13—C14	1.502 (3)
N3—H3	0.884 (9)	C14—H14A	0.9800
C1—C6	1.393 (3)	C14—H14B	0.9800
C1—C2	1.397 (3)	C14—H14C	0.9800
C2—C3	1.391 (3)	C15—C16	1.390 (3)
C2—H2	0.9500	C15—C20	1.397 (3)
C3—C4	1.382 (3)	C16—C17	1.389 (3)
C3—H3A	0.9500	C16—H16	0.9500
C4—C5	1.389 (3)	C17—C18	1.384 (3)
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.385 (3)	C18—C19	1.368 (3)
C5—H5	0.9500	C19—C20	1.387 (3)
C6—H6	0.9500	C19—H19	0.9500
C7—C8	1.388 (3)	C20—H20	0.9500

C7—O1—H1	102 (2)	H10A—C10—H10B	109.5
C7—N1—N2	110.10 (16)	C9—C10—H10C	109.5
C7—N1—C1	131.38 (18)	H10A—C10—H10C	109.5
N2—N1—C1	118.42 (16)	H10B—C10—H10C	109.5
C9—N2—N1	105.73 (17)	O2—C11—C12	121.97 (18)
C13—N3—C15	130.36 (18)	O2—C11—C8	116.11 (18)
C13—N3—H3	113.3 (15)	C12—C11—C8	121.92 (19)
C15—N3—H3	116.1 (16)	C13—C12—C11	125.6 (2)
C6—C1—C2	119.97 (19)	C13—C12—H12	117.2
C6—C1—N1	118.86 (19)	C11—C12—H12	117.2
C2—C1—N1	121.17 (19)	N3—C13—C12	120.95 (19)
C3—C2—C1	119.4 (2)	N3—C13—C14	120.42 (18)
C3—C2—H2	120.3	C12—C13—C14	118.62 (19)
C1—C2—H2	120.3	C13—C14—H14A	109.5
C4—C3—C2	120.6 (2)	C13—C14—H14B	109.5
C4—C3—H3A	119.7	H14A—C14—H14B	109.5
C2—C3—H3A	119.7	C13—C14—H14C	109.5
C3—C4—C5	119.8 (2)	H14A—C14—H14C	109.5
C3—C4—H4	120.1	H14B—C14—H14C	109.5
C5—C4—H4	120.1	C16—C15—C20	119.36 (19)
C6—C5—C4	120.3 (2)	C16—C15—N3	117.51 (18)
C6—C5—H5	119.9	C20—C15—N3	123.1 (2)
C4—C5—H5	119.9	C17—C16—C15	121.1 (2)
C5—C6—C1	119.9 (2)	C17—C16—H16	119.5
C5—C6—H6	120.0	C15—C16—H16	119.5
C1—C6—H6	120.0	C18—C17—C16	117.8 (2)
O1—C7—N1	124.71 (18)	C18—C17—H17	121.1
O1—C7—C8	127.17 (18)	C16—C17—H17	121.1
N1—C7—C8	108.11 (18)	F1—C18—C19	118.8 (2)
C7—C8—C9	104.59 (17)	F1—C18—C17	118.7 (2)
C7—C8—C11	119.57 (19)	C19—C18—C17	122.5 (2)
C9—C8—C11	135.84 (19)	C18—C19—C20	119.4 (2)
N2—C9—C8	111.47 (18)	C18—C19—H19	120.3
N2—C9—C10	119.03 (19)	C20—C19—H19	120.3
C8—C9—C10	129.50 (18)	C19—C20—C15	119.7 (2)
C9—C10—H10A	109.5	C19—C20—H20	120.1
C9—C10—H10B	109.5	C15—C20—H20	120.1

C7—N1—N2—C9	0.1 (2)	C11—C8—C9—N2	−179.7 (2)
C1—N1—N2—C9	176.80 (16)	C7—C8—C9—C10	179.2 (2)
C7—N1—C1—C6	172.3 (2)	C11—C8—C9—C10	−0.3 (4)
N2—N1—C1—C6	−3.6 (3)	C7—C8—C11—O2	−2.4 (3)
C7—N1—C1—C2	−7.6 (3)	C9—C8—C11—O2	177.0 (2)
N2—N1—C1—C2	176.52 (18)	C7—C8—C11—C12	177.68 (19)
C6—C1—C2—C3	−1.1 (3)	C9—C8—C11—C12	−2.9 (4)
N1—C1—C2—C3	178.82 (18)	O2—C11—C12—C13	1.2 (3)
C1—C2—C3—C4	0.5 (3)	C8—C11—C12—C13	−178.86 (19)
C2—C3—C4—C5	−0.1 (3)	C15—N3—C13—C12	179.61 (19)
C3—C4—C5—C6	0.2 (3)	C15—N3—C13—C14	0.7 (3)
C4—C5—C6—C1	−0.7 (3)	C11—C12—C13—N3	−1.2 (3)
C2—C1—C6—C5	1.2 (3)	C11—C12—C13—C14	177.71 (19)
N1—C1—C6—C5	−178.71 (17)	C13—N3—C15—C16	−149.5 (2)
N2—N1—C7—O1	178.72 (18)	C13—N3—C15—C20	33.5 (3)
C1—N1—C7—O1	2.6 (3)	C20—C15—C16—C17	−1.8 (3)
N2—N1—C7—C8	−0.3 (2)	N3—C15—C16—C17	−179.00 (19)
C1—N1—C7—C8	−176.41 (19)	C15—C16—C17—C18	−1.3 (3)
O1—C7—C8—C9	−178.6 (2)	C16—C17—C18—F1	−177.45 (19)
N1—C7—C8—C9	0.3 (2)	C16—C17—C18—C19	2.5 (3)
O1—C7—C8—C11	0.9 (3)	F1—C18—C19—C20	179.42 (18)
N1—C7—C8—C11	179.86 (17)	C17—C18—C19—C20	−0.5 (3)
N1—N2—C9—C8	0.1 (2)	C18—C19—C20—C15	−2.7 (3)
N1—N2—C9—C10	−179.39 (17)	C16—C15—C20—C19	3.8 (3)
C7—C8—C9—N2	−0.3 (2)	N3—C15—C20—C19	−179.17 (19)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C15–C20 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.86 (1)	1.73 (2)	2.521 (2)	152 (3)
N3—H3···O2	0.88 (1)	1.95 (2)	2.686 (2)	139 (2)
C14—H14A···F1ⁱ	0.98	2.43	3.309 (3)	150
C19—H19···O2ⁱⁱ	0.95	2.55	3.410 (3)	150
C16—H16···Cg1ⁱⁱⁱ	0.95	2.59	3.496 (3)	161

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x, y+1/2, −z+3/2; (iii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈FN₃O₂
M_r	351.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	8.3871 (7), 11.1368 (9), 18.4772 (16)
β (°)	101.317 (8)
V (Å³)	1692.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.05 × 0.02

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.981, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	7099, 3866, 2504
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.123, 1.05
No. of reflections	3866
No. of parameters	245
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.29

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C15–C20 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.86 (1)	1.73 (2)	2.521 (2)	152 (3)
N3—H3···O2	0.88 (1)	1.95 (2)	2.686 (2)	139 (2)
C14—H14A···F1ⁱ	0.98	2.43	3.309 (3)	150
C19—H19···O2ⁱⁱ	0.95	2.55	3.410 (3)	150
C16—H16···Cg1ⁱⁱⁱ	0.95	2.59	3.496 (3)	161

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x, y+1/2, −z+3/2; (iii) x, −y+1/2, z+1/2.

Footnotes

‡Additional correspondence author, e-mail: aasiri2@kau.edu.sa.

Acknowledgements

The authors are thankful to the Center of Excellence for Advanced Materials Research and the Chemistry Department of King Abdulaziz University for providing research facilities. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Asiri, A. M., Al-Youbi, A. O., Alamry, K. A., Faidallah, H. M., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o2157. Web of Science CSD CrossRef IUCr Journals Google Scholar
Asiri, A. M., Al-Youbi, A. O., Faidallah, H. M., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o2353. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bendaas, A., Hamdi, M. & Sellier, N. (1999). J. Heterocycl. Chem. 36, 1291–1294. CrossRef CAS Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gelin, S., Chantegrel, B. & Nadi, A. I. (1983). J. Org. Chem. 48, 4078–4082. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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(2Z)-3-(4-Fluoro­anilino)-1-(5-hy­dr­oxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)but-2-en-1-one

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Experimental

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organic compounds

(2Z)-3-(4-Fluoroanilino)-1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)but-2-en-1-one