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

Asiri, A.M.; Al-Youbi, A.O.; Alamry, K.A.; Faidallah, H.M.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536811029473

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2157

doi:10.1107/S1600536811029473

Open

access

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

Abdullah M. Asiri,^a,^b ‡ Abdulrahman O. Al-Youbi,^a Khalid A. Alamry,^a Hassan M. Faidallah,^a Seik Weng Ng ^c,^a 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 21 July 2011; accepted 21 July 2011; online 30 July 2011)

With the exception of the terminal benzene rings, the atoms in the title compound, C₂₀H₁₈ClN₃O₂, are approximately coplanar (r.m.s. deviation = 0.0495 Å). The benzene/chlorobenzene rings form dihedral angles of 3.02 (4) and 41.59 (5)°, respectively, with this plane. The hydroxy, amino and carbonyl groups all lie to the same side of the molecule, enabling the formation of intramolecular O—H⋯O and N—H⋯O hydrogen bonds that close S(6) rings. The configuration about the 2-butene bond is Z. Supramolecular chains mediated by C—H⋯Cl interactions and aligned along the c axis are found in the crystal packing. These assemble into layers that are connected by weak π–π interactions between centrosymmetrically related chlorobenzene 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_r = 367.82
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.103
S = 1.01
3860 reflections
245 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{3\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811029473/hg5069sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811029473/hg5069Isup3.cml

checkCIF report

Comment top

The title compound (I) was isolated during an investigation of reactions between pyrazoles and aniline derivatives following literature precedents (Gelin et al., 1983; Bendaas et al., 1999). The molecular structure of (I), Fig. 1, features a Z configuration about the C12—C13 [1.376 (2) Å] bond. The hydroxy and amino groups are syn to the central carbonyl group and each forms a hydrogen bond to close a S(6) ring (Table 1). A result of this feature of the structure is that the central residue is planar; the values of the C10—C9—C11–O2, C9—C11—C12—C13 and C11—C12—C13—N3 torsion angles are 2.5 (2), -177.93 (14) and -0.4 (2) °, respectively. Indeed, the r.m.s. deviation for the non-hydrogen atoms comprising the entire molecule excluding the terminal benzene rings is 0.0495 Å. The benzene and chlorobenzene rings form dihedral angles of 3.02 (4) and 41.59 (5) °, respectively, with the central plane.

The most prominent feature of the crystal packing is the formation of supramolecular chains mediated by C—H···Cl interactions, Table 1. The chains assemble into layers in the bc plane, Fig. 2. The closest interactions between layers stacking along the a direction are weak π–π contacts between centrosymmetrically related chlorobenzene rings [3.8156 (9) Å for symmetry operation: 2 - x, 1 - y, 2 - z].

Related literature top

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

Experimental top

A solution of 4-acetoacetyl-5-hydroxy-3-methyl-1-p-sulfamylphenypyrazole (1.7 g, 0.005 mol) and 4-chloroaniline (0.63 g, 0.005 mole) in ethanol (25 ml) was refluxed for 2 h. The precipitate, obtained from the hot solution, was collected, washed with methanol, and recrystallized from ethanol-benzene as orange crystals; M.pt 505–507 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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. Assembly of supramolecular chains aligned along the c axis in (I) mediated by C—H···Cl interactions shown as orange dashed lines.

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

Crystal data top

C₂₀H₁₈ClN₃O₂	F(000) = 768
M_r = 367.82	D_x = 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

Data collection top

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 monochromator	R_int = 0.025
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.5°
ω scans	h = −13→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −13→16
T_min = 0.931, T_max = 0.953	l = −15→16
8785 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)] = 0.039	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(F_o²) + (0.0495P)² + 0.5858P] where P = (F_o² + 2F_c²)/3
3860 reflections	(Δ/σ)_max < 0.001
245 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₀H₁₈ClN₃O₂	V = 1725.67 (9) Å³
M_r = 367.82	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.7782 (3) Å	µ = 0.24 mm⁻¹
b = 12.6349 (4) Å	T = 100 K
c = 12.9071 (4) Å	0.30 × 0.25 × 0.20 mm
β = 100.956 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3860 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3199 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.953	R_int = 0.025
8785 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.27 e Å⁻³
3860 reflections	Δρ_min = −0.30 e Å⁻³
245 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
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+3/2, z−3/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈ClN₃O₂
M_r	367.82
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	10.7782 (3), 12.6349 (4), 12.9071 (4)
β (°)	100.956 (3)
V (Å³)	1725.67 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.931, 0.953
No. of measured, independent and observed [I > 2σ(I)] reflections	8785, 3860, 3199
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.103, 1.01
No. of reflections	3860
No. of parameters	245
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.30

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

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+3/2, z−3/2.

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 at King Abdulaziz University for providing the research facilities. They also thank the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2157

doi:10.1107/S1600536811029473

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

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