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

With the exception of the terminal benzene rings, the atoms in the title compound, C(20)H(18)ClN(3)O(2), are approximately coplanar (r.m.s. deviation = 0.0495 Å). The benzene/chloro-benzene rings form dihedral angles of 3.02 (4) and 41.59 (5)°, respectively, with this plane. The hy-droxy, amino and carbonyl groups all lie to the same side of the mol-ecule, enabling the formation of intra-molecular O-H⋯O and N-H⋯O hydrogen bonds that close S(6) rings. The configuration about the 2-butene bond is Z. Supra-molecular chains mediated by C-H⋯Cl inter-actions and aligned along the c axis are found in the crystal packing. These assemble into layers that are connected by weak π-π inter-actions between centrosymmetrically related chloro-benzene rings [3.8156 (9) Å].

Related literature

For background to the synthesis, see: Gelin et al. (1983 ▶); Bendaas et al. (1999 ▶).

Experimental

Crystal data

C20H18ClN3O2

M = 367.82

Monoclinic,

a = 10.7782 (3) Å

b = 12.6349 (4) Å

c = 12.9071 (4) Å

β = 100.956 (3)°

V = 1725.67 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 100 K

0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.931, T max = 0.953

8785 measured reflections

3860 independent reflections

3199 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.103

S = 1.01

3860 reflections

245 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); 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/S1600536811029473/hg5069sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029473/hg5069Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029473/hg5069Isup3.cml

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

C20H18ClN3O2	F(000) = 768
Mr = 367.82	Dx = 1.416 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4068 reflections
a = 10.7782 (3) Å	θ = 2.5–29.3°
b = 12.6349 (4) Å	µ = 0.24 mm−1
c = 12.9071 (4) Å	T = 100 K
β = 100.956 (3)°	Block, orange
V = 1725.67 (9) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	3860 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3199 reflections with I > 2σ(I)
Mirror	Rint = 0.025
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.5°
ω scans	h = −13→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −13→16
Tmin = 0.931, Tmax = 0.953	l = −15→16
8785 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0495P)2 + 0.5858P] where P = (Fo2 + 2Fc2)/3
3860 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.30 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
Cl1	0.91036 (4)	0.59737 (3)	1.20821 (3)	0.02517 (13)
O1	0.69340 (10)	0.75724 (9)	0.38953 (9)	0.0208 (3)
O2	0.73186 (10)	0.65748 (9)	0.56249 (9)	0.0216 (3)
N1	0.59886 (11)	0.64664 (11)	0.24798 (10)	0.0184 (3)
N2	0.56236 (12)	0.54063 (11)	0.23365 (10)	0.0201 (3)
N3	0.77747 (12)	0.55053 (12)	0.74398 (11)	0.0200 (3)
C1	0.57853 (13)	0.71508 (14)	0.15919 (12)	0.0195 (3)
C2	0.60600 (15)	0.82241 (14)	0.17012 (13)	0.0238 (4)
H2	0.6377	0.8518	0.2377	0.029*
C3	0.58657 (16)	0.88614 (15)	0.08098 (14)	0.0290 (4)
H3A	0.6056	0.9595	0.0878	0.035*
C4	0.53986 (16)	0.84422 (16)	−0.01787 (14)	0.0291 (4)
H4	0.5276	0.8885	−0.0785	0.035*
C5	0.51121 (15)	0.73772 (16)	−0.02783 (13)	0.0282 (4)
H5	0.4780	0.7090	−0.0954	0.034*
C6	0.53058 (14)	0.67263 (15)	0.06000 (13)	0.0236 (4)
H6	0.5113	0.5993	0.0527	0.028*
C7	0.56011 (16)	0.38241 (13)	0.33884 (14)	0.0241 (4)
H7A	0.5145	0.3555	0.2710	0.036*
H7B	0.5070	0.3749	0.3922	0.036*
H7C	0.6383	0.3420	0.3606	0.036*
C8	0.59131 (13)	0.49623 (13)	0.32786 (12)	0.0193 (3)
C9	0.64770 (14)	0.57033 (13)	0.40580 (12)	0.0185 (3)
C10	0.64989 (13)	0.66471 (13)	0.35046 (12)	0.0175 (3)
C11	0.69441 (14)	0.56817 (13)	0.51866 (12)	0.0189 (3)
C12	0.69884 (14)	0.47308 (13)	0.57726 (13)	0.0210 (3)
H12	0.6726	0.4100	0.5393	0.025*
C13	0.73809 (14)	0.46454 (13)	0.68479 (13)	0.0196 (3)
C14	0.74065 (15)	0.35747 (13)	0.73563 (13)	0.0223 (4)
H14A	0.7539	0.3030	0.6848	0.033*
H14B	0.6601	0.3448	0.7581	0.033*
H14C	0.8097	0.3548	0.7971	0.033*
C15	0.80969 (14)	0.55777 (13)	0.85538 (12)	0.0187 (3)
C16	0.73868 (14)	0.50806 (14)	0.92039 (13)	0.0223 (4)
H16	0.6675	0.4665	0.8902	0.027*
C17	0.77113 (14)	0.51871 (14)	1.02897 (13)	0.0220 (4)
H17	0.7244	0.4827	1.0736	0.026*
C18	0.87226 (14)	0.58229 (13)	1.07155 (12)	0.0192 (3)
C19	0.94267 (14)	0.63411 (13)	1.00821 (13)	0.0199 (3)
H19	1.0115	0.6781	1.0386	0.024*
C20	0.91164 (14)	0.62108 (13)	0.89951 (13)	0.0192 (3)
H20	0.9601	0.6555	0.8552	0.023*
H1	0.721 (3)	0.739 (2)	0.462 (2)	0.077 (9)*
H3	0.7859 (18)	0.6100 (17)	0.7060 (17)	0.035 (6)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0307 (2)	0.0284 (2)	0.0149 (2)	0.00130 (16)	0.00068 (15)	−0.00084 (17)
O1	0.0259 (6)	0.0178 (6)	0.0170 (6)	−0.0017 (4)	0.0000 (4)	−0.0009 (5)
O2	0.0283 (6)	0.0188 (6)	0.0167 (6)	−0.0025 (5)	0.0019 (4)	−0.0017 (5)
N1	0.0190 (6)	0.0191 (7)	0.0162 (7)	−0.0017 (5)	0.0013 (5)	−0.0003 (6)
N2	0.0225 (7)	0.0184 (7)	0.0186 (7)	−0.0019 (5)	0.0019 (5)	−0.0015 (6)
N3	0.0245 (7)	0.0193 (7)	0.0150 (7)	−0.0012 (5)	0.0009 (5)	0.0018 (6)
C1	0.0151 (7)	0.0269 (9)	0.0164 (8)	0.0016 (6)	0.0031 (6)	0.0032 (7)
C2	0.0229 (8)	0.0279 (10)	0.0200 (8)	−0.0024 (7)	0.0029 (6)	0.0012 (7)
C3	0.0313 (9)	0.0291 (10)	0.0264 (9)	−0.0025 (7)	0.0051 (7)	0.0066 (8)
C4	0.0290 (9)	0.0385 (11)	0.0195 (9)	0.0003 (8)	0.0039 (7)	0.0096 (8)
C5	0.0255 (8)	0.0433 (12)	0.0152 (8)	0.0010 (8)	0.0021 (6)	0.0013 (8)
C6	0.0226 (8)	0.0293 (10)	0.0187 (8)	−0.0006 (7)	0.0037 (6)	−0.0018 (7)
C7	0.0285 (8)	0.0201 (9)	0.0226 (9)	−0.0031 (7)	0.0019 (7)	−0.0038 (7)
C8	0.0187 (7)	0.0207 (9)	0.0185 (8)	0.0010 (6)	0.0033 (6)	−0.0015 (7)
C9	0.0195 (7)	0.0190 (8)	0.0169 (8)	0.0004 (6)	0.0030 (6)	−0.0008 (7)
C10	0.0152 (7)	0.0204 (8)	0.0167 (8)	0.0003 (6)	0.0023 (6)	−0.0022 (7)
C11	0.0187 (7)	0.0215 (8)	0.0166 (8)	0.0008 (6)	0.0043 (6)	−0.0016 (7)
C12	0.0236 (8)	0.0200 (9)	0.0190 (8)	0.0001 (6)	0.0032 (6)	−0.0017 (7)
C13	0.0173 (7)	0.0202 (8)	0.0214 (8)	0.0005 (6)	0.0037 (6)	−0.0007 (7)
C14	0.0244 (8)	0.0200 (9)	0.0210 (9)	−0.0009 (6)	0.0009 (6)	0.0010 (7)
C15	0.0206 (7)	0.0187 (8)	0.0156 (8)	0.0036 (6)	0.0006 (6)	−0.0001 (6)
C16	0.0189 (7)	0.0261 (9)	0.0209 (8)	−0.0038 (6)	0.0012 (6)	−0.0004 (7)
C17	0.0229 (8)	0.0239 (9)	0.0198 (8)	0.0002 (6)	0.0052 (6)	0.0016 (7)
C18	0.0221 (7)	0.0195 (8)	0.0145 (8)	0.0052 (6)	−0.0002 (6)	0.0007 (6)
C19	0.0212 (8)	0.0164 (8)	0.0204 (8)	0.0008 (6)	0.0000 (6)	−0.0015 (7)
C20	0.0225 (8)	0.0155 (8)	0.0196 (8)	0.0018 (6)	0.0041 (6)	0.0016 (6)

Cl1—C18	1.7438 (16)	C7—H7A	0.9800
O1—C10	1.3233 (19)	C7—H7B	0.9800
O1—H1	0.96 (3)	C7—H7C	0.9800
O2—C11	1.2921 (19)	C8—C9	1.423 (2)
N1—C10	1.3519 (19)	C9—C10	1.392 (2)
N1—N2	1.3984 (19)	C9—C11	1.448 (2)
N1—C1	1.419 (2)	C11—C12	1.416 (2)
N2—C8	1.321 (2)	C12—C13	1.376 (2)
N3—C13	1.349 (2)	C12—H12	0.9500
N3—C15	1.417 (2)	C13—C14	1.502 (2)
N3—H3	0.91 (2)	C14—H14A	0.9800
C1—C2	1.389 (2)	C14—H14B	0.9800
C1—C6	1.394 (2)	C14—H14C	0.9800
C2—C3	1.387 (2)	C15—C20	1.391 (2)
C2—H2	0.9500	C15—C16	1.389 (2)
C3—C4	1.385 (3)	C16—C17	1.385 (2)
C3—H3A	0.9500	C16—H16	0.9500
C4—C5	1.381 (3)	C17—C18	1.381 (2)
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.384 (2)	C18—C19	1.382 (2)
C5—H5	0.9500	C19—C20	1.389 (2)
C6—H6	0.9500	C19—H19	0.9500
C7—C8	1.490 (2)	C20—H20	0.9500
C10—O1—H1	100.3 (17)	C8—C9—C11	135.94 (15)
C10—N1—N2	110.06 (13)	O1—C10—N1	124.81 (14)
C10—N1—C1	131.22 (14)	O1—C10—C9	126.90 (14)
N2—N1—C1	118.72 (13)	N1—C10—C9	108.29 (14)
C8—N2—N1	105.88 (12)	O2—C11—C12	122.09 (14)
C13—N3—C15	128.07 (15)	O2—C11—C9	116.35 (14)
C13—N3—H3	114.3 (13)	C12—C11—C9	121.56 (15)
C15—N3—H3	117.6 (13)	C13—C12—C11	125.31 (16)
C2—C1—C6	120.24 (15)	C13—C12—H12	117.3
C2—C1—N1	121.03 (15)	C11—C12—H12	117.3
C6—C1—N1	118.73 (15)	N3—C13—C12	120.74 (15)
C1—C2—C3	119.12 (16)	N3—C13—C14	120.02 (14)
C1—C2—H2	120.4	C12—C13—C14	119.21 (15)
C3—C2—H2	120.4	C13—C14—H14A	109.5
C4—C3—C2	120.88 (18)	C13—C14—H14B	109.5
C4—C3—H3A	119.6	H14A—C14—H14B	109.5
C2—C3—H3A	119.6	C13—C14—H14C	109.5
C5—C4—C3	119.61 (17)	H14A—C14—H14C	109.5
C5—C4—H4	120.2	H14B—C14—H14C	109.5
C3—C4—H4	120.2	C20—C15—C16	119.74 (15)
C4—C5—C6	120.43 (17)	C20—C15—N3	118.36 (14)
C4—C5—H5	119.8	C16—C15—N3	121.82 (14)
C6—C5—H5	119.8	C17—C16—C15	120.35 (15)
C5—C6—C1	119.71 (17)	C17—C16—H16	119.8
C5—C6—H6	120.1	C15—C16—H16	119.8
C1—C6—H6	120.1	C18—C17—C16	119.18 (15)
C8—C7—H7A	109.5	C18—C17—H17	120.4
C8—C7—H7B	109.5	C16—C17—H17	120.4
H7A—C7—H7B	109.5	C19—C18—C17	121.39 (15)
C8—C7—H7C	109.5	C19—C18—Cl1	119.77 (12)
H7A—C7—H7C	109.5	C17—C18—Cl1	118.84 (13)
H7B—C7—H7C	109.5	C18—C19—C20	119.19 (15)
N2—C8—C9	111.44 (14)	C18—C19—H19	120.4
N2—C8—C7	118.63 (14)	C20—C19—H19	120.4
C9—C8—C7	129.91 (15)	C19—C20—C15	120.12 (15)
C10—C9—C8	104.32 (14)	C19—C20—H20	119.9
C10—C9—C11	119.70 (15)	C15—C20—H20	119.9
C10—N1—N2—C8	0.30 (16)	C11—C9—C10—O1	1.3 (2)
C1—N1—N2—C8	−179.71 (12)	C8—C9—C10—N1	−0.15 (16)
C10—N1—C1—C2	−3.9 (2)	C11—C9—C10—N1	−178.50 (13)
N2—N1—C1—C2	176.08 (13)	C10—C9—C11—O2	2.5 (2)
C10—N1—C1—C6	175.87 (14)	C8—C9—C11—O2	−175.18 (16)
N2—N1—C1—C6	−4.1 (2)	C10—C9—C11—C12	−177.32 (14)
C6—C1—C2—C3	−0.8 (2)	C8—C9—C11—C12	5.0 (3)
N1—C1—C2—C3	178.97 (14)	O2—C11—C12—C13	2.2 (2)
C1—C2—C3—C4	0.3 (2)	C9—C11—C12—C13	−177.93 (14)
C2—C3—C4—C5	0.5 (3)	C15—N3—C13—C12	173.70 (14)
C3—C4—C5—C6	−0.9 (3)	C15—N3—C13—C14	−8.2 (2)
C4—C5—C6—C1	0.4 (2)	C11—C12—C13—N3	−0.4 (2)
C2—C1—C6—C5	0.4 (2)	C11—C12—C13—C14	−178.47 (14)
N1—C1—C6—C5	−179.35 (14)	C13—N3—C15—C20	141.37 (16)
N1—N2—C8—C9	−0.40 (16)	C13—N3—C15—C16	−42.0 (2)
N1—N2—C8—C7	178.35 (13)	C20—C15—C16—C17	−1.9 (2)
N2—C8—C9—C10	0.35 (17)	N3—C15—C16—C17	−178.53 (15)
C7—C8—C9—C10	−178.22 (15)	C15—C16—C17—C18	2.2 (2)
N2—C8—C9—C11	178.29 (16)	C16—C17—C18—C19	−1.0 (2)
C7—C8—C9—C11	−0.3 (3)	C16—C17—C18—Cl1	178.69 (12)
N2—N1—C10—O1	−179.86 (13)	C17—C18—C19—C20	−0.6 (2)
C1—N1—C10—O1	0.1 (2)	Cl1—C18—C19—C20	179.74 (12)
N2—N1—C10—C9	−0.08 (16)	C18—C19—C20—C15	0.9 (2)
C1—N1—C10—C9	179.92 (14)	C16—C15—C20—C19	0.3 (2)
C8—C9—C10—O1	179.62 (14)	N3—C15—C20—C19	177.05 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.96 (3)	1.64 (3)	2.5283 (16)	153 (3)
N3—H3···O2	0.91 (2)	1.93 (2)	2.6678 (18)	136.9 (18)
C4—H4···Cl1i	0.95	2.81	3.6217 (18)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.96 (3)	1.64 (3)	2.5283 (16)	153 (3)
N3—H3⋯O2	0.91 (2)	1.93 (2)	2.6678 (18)	136.9 (18)
C4—H4⋯Cl1i	0.95	2.81	3.6217 (18)	144

Symmetry code: (i) .