(2Z)-3-(4-Fluoro-anilino)-1-(5-hy-droxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)but-2-en-1-one.

The central carbonyl group in the title compound, C(20)H(18)FN(3)O(2), forms amine-hy-droxy N-H⋯O and hy-droxy-hy-droxy 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 mol-ecule is evident, the dihedral angle between the terminal phenyl and benzene rings being 27.30 (10)°. Mol-ecules aggregate into a three-dimensional architecture via C-H⋯F, C-H⋯O and C-H⋯π inter-actions.

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 = 351.37

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.123

S = 1.05

3866 reflections

245 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.29 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812006514/hg5178sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812006514/hg5178Isup3.cml

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

C20H18FN3O2	F(000) = 736
Mr = 351.37	Dx = 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

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	Rint = 0.038
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.5°
ω scan	h = −7→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −10→14
Tmin = 0.981, Tmax = 0.998	l = −22→24
7099 measured reflections

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(Fo2) + (0.0355P)2] where P = (Fo2 + 2Fc2)/3
3866 reflections	(Δ/σ)max = 0.001
245 parameters	Δρmax = 0.25 e Å−3
2 restraints	Δρmin = −0.29 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .