(4Z)-4-[(2-Chloro­anilino)(phen­yl)methyl­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Xu, L.-Y.; Li, N.; Li, J.-M.; Zhang, H.-Q.; Sun, Z.-H.

doi:10.1107/S1600536812020004

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1843

doi:10.1107/S1600536812020004

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(4Z)-4-[(2-Chloroanilino)(phenyl)methylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Li-Ying Xu,^a,^b Ning Li,^a ^* Jia-Min Li,^c Heng-Qiang Zhang ^d and Zhen-Hai Sun ^b

^aSchool of Chemical Engineering and Technology, Harbin Institute of Technology, Harbin 150001, People's Republic of China, ^bSchool of Science, Harbin University, Harbin 150080, People's Republic of China, ^cSchool of Science, Northeast Forestry University, Harbin 150040, People's Republic of China, and ^dDepartment of Chemistry, East China Normal University, Shanghai 200062, People's Republic of China
^*Correspondence e-mail: lining1957@126.com

(Received 18 April 2012; accepted 4 May 2012; online 23 May 2012)

The title compound, C₂₃H₁₈ClN₃O, exists in an enamine–keto form with the amino group involved in an intramolecular N—H⋯O hydrogen bond. The five-membered ring is nearly planar, the largest deviation being 0.0004 (7) Å, and makes dihedral angles of 16.62 (6), 41.89 (5) and 71.27 (4)° with the phenyl rings. In the crystal, weak C—H⋯O hydrogen bonds link the molecules into supramolecular chains along the b axis.

Related literature

For general background to Schiff bases derived from 1-phenyl-3-methyl-4-benzoyl-1H-pyrazol-5(4H)-one and their pharmaceutical and agrochemical applications, see: Casas et al. (2007 ); Zhang et al. (2008 ). For related structures, see: Zhang et al. (2007 ); Li et al. (2009 ); Chi et al. (2010 ).

Experimental

Crystal data

C₂₃H₁₈ClN₃O
M_r = 387.85
Monoclinic, P 2₁ /n
a = 9.0425 (3) Å
b = 18.5180 (7) Å
c = 11.1983 (4) Å
β = 90.423 (1)°
V = 1875.09 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.951, T_max = 0.959
17018 measured reflections
4637 independent reflections
4251 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.095
S = 1.04
4613 reflections
258 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1	0.879 (18)	1.915 (18)	2.6800 (14)	144.5 (16)
C6—H6⋯O1	0.93	2.31	2.9027 (16)	121
C16—H16⋯O1ⁱ	0.93	2.56	3.4797 (17)	170
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812020004/zq2164sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812020004/zq2164Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812020004/zq2164Isup3.cml

checkCIF report

Comment top

The 1-phenyl-3-methyl-4-benzoyl-1H-pyrazol-5(4H)-ones (PMBP) are a novel type of β-enaminoketone. The Schiff bases derived from PMBP have attracted much attention due to their applications in pharmaceutical and agrochemical fields (e.g. Casas et al., 2007; Zhang et al., 2008). In order to expand this field, we now report the synthesis and structure of the title compound.

The molecular structure of the title compound is shown in Fig.1. Atoms O1, C10, C9 and C11 of the PMBP moiety and atom N3 of the o-chloroaniline group are coplanar, the largest deviation being 0.038 (11) Å for atom C10. The dihedral angle between this mean plane and the pyrazole ring of PMBP is 5.76 (3)°. The C9—C11 bond length of 1.3887 (15) Å, between usual C—C and C=C bond, indicates the delocalization of the electrons because of the addition of a proton to N3 is more favorable than to O2. The atom O2 of the PMBP moiety and the N3 atom of the o-chloroaniline group are on the same side of the C9—C11 bond, which are available for coordination with metal cations. A strong intramolecular hydrogen bond N3—H3A···O1 (Table 1) is also indicative of the enamine-keto form. In the crystal structure, the intramolecular hydrogen bond C6—H6···O1 and intermolecular hydrogen bond C16—H16···O1 are observed, the latter links the molecules into supramolecular chains along the b axis. All bond lengths and angles are normal and comparable with those found in related compounds (Zhang et al., 2007; Li et al., 2009; Chi et al., 2010).

Related literature top

For general background to Schiff bases derived from 1-phenyl-3-methyl-4-benzoyl-1H-pyrazol-5(4H)-one and their pharmaceutical and agrochemical applications, see: Casas et al. (2007); Zhang et al. (2008). For related structures, see: Zhang et al. (2007); Li et al. (2009); Chi et al. (2010).

Experimental top

A mixture of a 10 ml PMBP (2 mmol, 0.5566 g) anhydrous ethanol solution, and a 0.21 ml of an o-chloroaniline (2 mmol, 0.2545 g) solution was refluxed for ca 5 h, with addition of a few drops of glacial acetic acid as a catalyst. The ethanol was removed by evaporation and the resulting green precipitate formed was filtered off, washed with cold anhydrous ethanol and dried in air. Yellow block single crystals suitable for analysis were obtained by slow evaporation of a solution in anhydrous ethanol at room temperature for a few days.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound (thermal ellipsoids are shown at the 30% probability level).

(4Z)-4-[(2-Chloroanilino)(phenyl)methylidene]-3-methyl-1-phenyl- 1H-pyrazol-5(4H)-one top

Crystal data top

C₂₃H₁₈ClN₃O	F(000) = 808.0
M_r = 387.85	D_x = 1.374 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2yn	Cell parameters from 9949 reflections
a = 9.0425 (3) Å	θ = 3.1–28.2°
b = 18.5180 (7) Å	µ = 0.22 mm⁻¹
c = 11.1983 (4) Å	T = 296 K
β = 90.423 (1)°	Block, yellow
V = 1875.09 (12) Å³	0.22 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	4637 independent reflections
Radiation source: fine-focus sealed tube	4251 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
ω scans	θ_max = 28.2°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
T_min = 0.951, T_max = 0.959	k = −24→23
17018 measured reflections	l = −14→14

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0482P)² + 0.9306P] where P = (F_o² + 2F_c²)/3
4613 reflections	(Δ/σ)_max < 0.001
258 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₂₃H₁₈ClN₃O	V = 1875.09 (12) Å³
M_r = 387.85	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.0425 (3) Å	µ = 0.22 mm⁻¹
b = 18.5180 (7) Å	T = 296 K
c = 11.1983 (4) Å	0.22 × 0.20 × 0.18 mm
β = 90.423 (1)°

Data collection top

Bruker SMART CCD diffractometer	4637 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4251 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.959	R_int = 0.013
17018 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.37 e Å⁻³
4613 reflections	Δρ_min = −0.34 e Å⁻³
258 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
C1	0.86725 (13)	−0.06692 (6)	−0.09829 (10)	0.0186 (2)
C2	0.87873 (15)	−0.07367 (7)	−0.22145 (11)	0.0238 (2)
H2	0.8476	−0.0364	−0.2713	0.029*
C3	0.93725 (15)	−0.13668 (7)	−0.26969 (12)	0.0271 (3)
H3	0.9454	−0.1413	−0.3521	0.033*
C4	0.98343 (14)	−0.19250 (7)	−0.19629 (12)	0.0253 (3)
H4	1.0181	−0.2354	−0.2291	0.030*
C5	0.97757 (15)	−0.18398 (7)	−0.07385 (12)	0.0284 (3)
H5	1.0116	−0.2208	−0.0242	0.034*
C6	0.92153 (15)	−0.12112 (7)	−0.02397 (11)	0.0260 (3)
H6	0.9203	−0.1153	0.0585	0.031*
C7	0.70636 (14)	0.10296 (6)	−0.05496 (10)	0.0196 (2)
C8	0.67068 (17)	0.17489 (7)	−0.10804 (11)	0.0269 (3)
H8A	0.7155	0.1787	−0.1852	0.040*
H8B	0.7083	0.2124	−0.0570	0.040*
H8C	0.5654	0.1798	−0.1161	0.040*
C9	0.68060 (13)	0.07593 (6)	0.06368 (10)	0.0187 (2)
C10	0.74394 (13)	0.00384 (6)	0.06478 (10)	0.0198 (2)
C11	0.62430 (12)	0.10790 (6)	0.16590 (10)	0.0164 (2)
C12	0.56486 (12)	0.18268 (6)	0.16522 (10)	0.0169 (2)
C13	0.43881 (14)	0.20000 (7)	0.09874 (11)	0.0234 (2)
H13	0.3877	0.1641	0.0577	0.028*
C14	0.38969 (16)	0.27111 (8)	0.09393 (13)	0.0326 (3)
H14	0.3046	0.2826	0.0509	0.039*
C15	0.46709 (18)	0.32468 (7)	0.15296 (14)	0.0359 (3)
H15	0.4353	0.3723	0.1478	0.043*
C16	0.59174 (17)	0.30782 (7)	0.21975 (13)	0.0318 (3)
H16	0.6434	0.3442	0.2594	0.038*
C17	0.63988 (14)	0.23657 (7)	0.22775 (11)	0.0225 (2)
H17	0.7218	0.2250	0.2747	0.027*
C18	0.57642 (12)	0.08798 (6)	0.38216 (9)	0.0161 (2)
C19	0.43971 (13)	0.12143 (6)	0.39789 (10)	0.0189 (2)
H19	0.3851	0.1365	0.3317	0.023*
C20	0.38483 (13)	0.13232 (6)	0.51203 (11)	0.0211 (2)
H20	0.2938	0.1548	0.5218	0.025*
C21	0.46478 (14)	0.10990 (6)	0.61183 (10)	0.0213 (2)
H21	0.4270	0.1172	0.6879	0.026*
C22	0.60091 (13)	0.07666 (6)	0.59773 (10)	0.0196 (2)
H22	0.6550	0.0616	0.6642	0.024*
C23	0.65570 (12)	0.06605 (6)	0.48371 (10)	0.0166 (2)
Cl1	0.82565 (3)	0.023579 (16)	0.46642 (3)	0.02280 (9)
H3A	0.678 (2)	0.0288 (10)	0.2610 (16)	0.034 (5)*
N1	0.79928 (12)	−0.00523 (5)	−0.04860 (8)	0.0200 (2)
N2	0.77460 (12)	0.05536 (5)	−0.12101 (9)	0.0210 (2)
N3	0.63332 (12)	0.07069 (6)	0.26879 (8)	0.0194 (2)
O1	0.74879 (11)	−0.04063 (5)	0.14826 (8)	0.0267 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0193 (5)	0.0172 (5)	0.0194 (5)	0.0015 (4)	0.0010 (4)	−0.0038 (4)
C2	0.0306 (6)	0.0216 (6)	0.0193 (5)	0.0019 (5)	0.0034 (5)	−0.0022 (4)
C3	0.0305 (6)	0.0278 (7)	0.0232 (6)	0.0001 (5)	0.0044 (5)	−0.0099 (5)
C4	0.0191 (5)	0.0218 (6)	0.0349 (7)	0.0013 (4)	0.0014 (5)	−0.0117 (5)
C5	0.0285 (6)	0.0243 (6)	0.0322 (7)	0.0094 (5)	−0.0021 (5)	−0.0023 (5)
C6	0.0308 (6)	0.0258 (6)	0.0214 (6)	0.0095 (5)	−0.0013 (5)	−0.0023 (5)
C7	0.0268 (6)	0.0176 (5)	0.0143 (5)	0.0023 (4)	0.0000 (4)	0.0007 (4)
C8	0.0436 (7)	0.0197 (6)	0.0177 (5)	0.0079 (5)	0.0046 (5)	0.0039 (4)
C9	0.0255 (6)	0.0154 (5)	0.0152 (5)	0.0036 (4)	0.0005 (4)	0.0012 (4)
C10	0.0256 (6)	0.0175 (5)	0.0164 (5)	0.0044 (4)	0.0019 (4)	0.0001 (4)
C11	0.0179 (5)	0.0160 (5)	0.0152 (5)	0.0010 (4)	−0.0007 (4)	0.0006 (4)
C12	0.0195 (5)	0.0155 (5)	0.0158 (5)	0.0015 (4)	0.0042 (4)	0.0011 (4)
C13	0.0227 (6)	0.0242 (6)	0.0232 (6)	0.0036 (5)	0.0015 (4)	0.0052 (4)
C14	0.0303 (7)	0.0321 (7)	0.0356 (7)	0.0139 (6)	0.0092 (5)	0.0139 (6)
C15	0.0444 (8)	0.0186 (6)	0.0452 (8)	0.0103 (6)	0.0247 (7)	0.0082 (6)
C16	0.0402 (8)	0.0192 (6)	0.0362 (7)	−0.0072 (5)	0.0213 (6)	−0.0073 (5)
C17	0.0229 (6)	0.0225 (6)	0.0222 (5)	−0.0036 (4)	0.0078 (4)	−0.0049 (4)
C18	0.0201 (5)	0.0140 (5)	0.0143 (5)	−0.0007 (4)	0.0023 (4)	0.0001 (4)
C19	0.0202 (5)	0.0171 (5)	0.0193 (5)	0.0009 (4)	0.0017 (4)	0.0016 (4)
C20	0.0222 (5)	0.0159 (5)	0.0251 (6)	0.0001 (4)	0.0074 (4)	−0.0003 (4)
C21	0.0290 (6)	0.0176 (5)	0.0175 (5)	−0.0040 (4)	0.0077 (4)	−0.0023 (4)
C22	0.0263 (6)	0.0174 (5)	0.0151 (5)	−0.0040 (4)	−0.0003 (4)	0.0007 (4)
C23	0.0167 (5)	0.0149 (5)	0.0182 (5)	−0.0015 (4)	0.0008 (4)	0.0005 (4)
Cl1	0.01928 (14)	0.02670 (16)	0.02240 (15)	0.00267 (10)	−0.00047 (10)	0.00295 (10)
N1	0.0294 (5)	0.0163 (5)	0.0142 (4)	0.0054 (4)	0.0020 (4)	0.0006 (3)
N2	0.0311 (5)	0.0170 (5)	0.0150 (4)	0.0037 (4)	0.0003 (4)	0.0018 (4)
N3	0.0254 (5)	0.0179 (5)	0.0148 (4)	0.0072 (4)	0.0028 (4)	0.0007 (3)
O1	0.0408 (5)	0.0208 (4)	0.0186 (4)	0.0113 (4)	0.0073 (4)	0.0054 (3)

Geometric parameters (Å, º) top

C1—C2	1.3895 (16)	C12—C13	1.3941 (16)
C1—C6	1.3910 (17)	C13—C14	1.3906 (18)
C1—N1	1.4133 (14)	C13—H13	0.9300
C2—C3	1.3920 (17)	C14—C15	1.380 (2)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.383 (2)	C15—C16	1.384 (2)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.3816 (19)	C16—C17	1.3921 (19)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.3885 (18)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.3950 (16)
C6—H6	0.9300	C18—C23	1.4000 (15)
C7—N2	1.3084 (15)	C18—N3	1.4102 (14)
C7—C9	1.4403 (15)	C19—C20	1.3892 (16)
C7—C8	1.4928 (16)	C19—H19	0.9300
C8—H8A	0.9600	C20—C21	1.3900 (18)
C8—H8B	0.9600	C20—H20	0.9300
C8—H8C	0.9600	C21—C22	1.3863 (17)
C9—C11	1.3887 (15)	C21—H21	0.9300
C9—C10	1.4526 (16)	C22—C23	1.3870 (15)
C10—O1	1.2464 (14)	C22—H22	0.9300
C10—N1	1.3784 (14)	C23—Cl1	1.7384 (11)
C11—N3	1.3445 (14)	N1—N2	1.4012 (13)
C11—C12	1.4855 (15)	N3—H3A	0.877 (19)
C12—C17	1.3925 (16)

C2—C1—C6	120.02 (11)	C14—C13—H13	120.1
C2—C1—N1	119.96 (11)	C12—C13—H13	120.1
C6—C1—N1	120.02 (10)	C15—C14—C13	120.10 (13)
C1—C2—C3	119.47 (12)	C15—C14—H14	120.0
C1—C2—H2	120.3	C13—C14—H14	120.0
C3—C2—H2	120.3	C14—C15—C16	120.34 (12)
C4—C3—C2	120.65 (12)	C14—C15—H15	119.8
C4—C3—H3	119.7	C16—C15—H15	119.8
C2—C3—H3	119.7	C15—C16—C17	120.11 (13)
C5—C4—C3	119.39 (12)	C15—C16—H16	119.9
C5—C4—H4	120.3	C17—C16—H16	119.9
C3—C4—H4	120.3	C16—C17—C12	119.73 (12)
C4—C5—C6	120.78 (12)	C16—C17—H17	120.1
C4—C5—H5	119.6	C12—C17—H17	120.1
C6—C5—H5	119.6	C19—C18—C23	118.37 (10)
C5—C6—C1	119.50 (12)	C19—C18—N3	122.96 (10)
C5—C6—H6	120.2	C23—C18—N3	118.51 (10)
C1—C6—H6	120.2	C20—C19—C18	120.23 (11)
N2—C7—C9	111.56 (10)	C20—C19—H19	119.9
N2—C7—C8	118.52 (10)	C18—C19—H19	119.9
C9—C7—C8	129.90 (10)	C19—C20—C21	120.61 (11)
C7—C8—H8A	109.5	C19—C20—H20	119.7
C7—C8—H8B	109.5	C21—C20—H20	119.7
H8A—C8—H8B	109.5	C22—C21—C20	119.87 (11)
C7—C8—H8C	109.5	C22—C21—H21	120.1
H8A—C8—H8C	109.5	C20—C21—H21	120.1
H8B—C8—H8C	109.5	C21—C22—C23	119.42 (11)
C11—C9—C7	132.45 (11)	C21—C22—H22	120.3
C11—C9—C10	122.12 (10)	C23—C22—H22	120.3
C7—C9—C10	105.11 (10)	C22—C23—C18	121.49 (10)
O1—C10—N1	126.82 (11)	C22—C23—Cl1	119.26 (9)
O1—C10—C9	128.70 (11)	C18—C23—Cl1	119.25 (9)
N1—C10—C9	104.48 (9)	C10—N1—N2	112.22 (9)
N3—C11—C9	117.88 (10)	C10—N1—C1	128.54 (10)
N3—C11—C12	120.12 (10)	N2—N1—C1	119.16 (9)
C9—C11—C12	121.87 (10)	C7—N2—N1	106.62 (9)
C17—C12—C13	119.80 (11)	C11—N3—C18	129.41 (10)
C17—C12—C11	119.38 (10)	C11—N3—H3A	113.1 (12)
C13—C12—C11	120.77 (10)	C18—N3—H3A	117.4 (12)
C14—C13—C12	119.87 (13)

C6—C1—C2—C3	3.56 (19)	C13—C12—C17—C16	−2.44 (17)
N1—C1—C2—C3	−175.90 (12)	C11—C12—C17—C16	174.82 (11)
C1—C2—C3—C4	0.2 (2)	C23—C18—C19—C20	−0.05 (17)
C2—C3—C4—C5	−3.0 (2)	N3—C18—C19—C20	175.29 (11)
C3—C4—C5—C6	2.1 (2)	C18—C19—C20—C21	−0.23 (18)
C4—C5—C6—C1	1.6 (2)	C19—C20—C21—C22	0.31 (18)
C2—C1—C6—C5	−4.49 (19)	C20—C21—C22—C23	−0.10 (17)
N1—C1—C6—C5	174.98 (12)	C21—C22—C23—C18	−0.18 (17)
N2—C7—C9—C11	174.02 (13)	C21—C22—C23—Cl1	−179.40 (9)
C8—C7—C9—C11	−4.3 (2)	C19—C18—C23—C22	0.26 (17)
N2—C7—C9—C10	0.57 (14)	N3—C18—C23—C22	−175.30 (10)
C8—C7—C9—C10	−177.72 (13)	C19—C18—C23—Cl1	179.47 (8)
C11—C9—C10—O1	5.5 (2)	N3—C18—C23—Cl1	3.92 (14)
C7—C9—C10—O1	179.79 (13)	O1—C10—N1—N2	179.70 (12)
C11—C9—C10—N1	−174.35 (11)	C9—C10—N1—N2	−0.45 (13)
C7—C9—C10—N1	−0.05 (13)	O1—C10—N1—C1	3.2 (2)
C7—C9—C11—N3	−170.78 (12)	C9—C10—N1—C1	−176.98 (11)
C10—C9—C11—N3	1.74 (17)	C2—C1—N1—C10	161.96 (12)
C7—C9—C11—C12	5.1 (2)	C6—C1—N1—C10	−17.50 (19)
C10—C9—C11—C12	177.64 (11)	C2—C1—N1—N2	−14.36 (17)
N3—C11—C12—C17	63.52 (15)	C6—C1—N1—N2	166.17 (11)
C9—C11—C12—C17	−112.29 (13)	C9—C7—N2—N1	−0.83 (14)
N3—C11—C12—C13	−119.24 (13)	C8—C7—N2—N1	177.68 (11)
C9—C11—C12—C13	64.95 (15)	C10—N1—N2—C7	0.81 (14)
C17—C12—C13—C14	0.82 (18)	C1—N1—N2—C7	177.71 (11)
C11—C12—C13—C14	−176.41 (11)	C9—C11—N3—C18	−175.06 (11)
C12—C13—C14—C15	1.23 (19)	C12—C11—N3—C18	8.97 (18)
C13—C14—C15—C16	−1.7 (2)	C19—C18—N3—C11	37.69 (18)
C14—C15—C16—C17	0.0 (2)	C23—C18—N3—C11	−146.98 (12)
C15—C16—C17—C12	2.03 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.879 (18)	1.915 (18)	2.6800 (14)	144.5 (16)
C6—H6···O1	0.93	2.31	2.9027 (16)	121
C16—H16···O1ⁱ	0.93	2.56	3.4797 (17)	170

Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₈ClN₃O
M_r	387.85
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	9.0425 (3), 18.5180 (7), 11.1983 (4)
β (°)	90.423 (1)
V (Å³)	1875.09 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.951, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	17018, 4637, 4251
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.095, 1.04
No. of reflections	4613
No. of parameters	258
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.34

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.879 (18)	1.915 (18)	2.6800 (14)	144.5 (16)
C6—H6···O1	0.93	2.31	2.9027 (16)	121
C16—H16···O1ⁱ	0.93	2.56	3.4797 (17)	170

Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.

Acknowledgements

This work was supported by the Scientific Research Foundation of the Education Department of Heilongjiang Province (grant No. 12513059), the Youth Foundation of Harbin University (grant No. HXKQ200610) and the Fundamental Research Funds for the Central Universities (grant No. DL11BB28).

References

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Casas, J. S., García-Tasende, M. S., Sánchez, A., Sordo, J. & Touceda, Á. (2007). Coord. Chem. Rev. 251, 1561–1589. CrossRef CAS Google Scholar
Chi, X., Xiao, J., Yin, Y. & Xia, M. (2010). Acta Cryst. E66, o249. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, J., Li, J.-Z., Li, J.-Q., Zhang, H.-Q. & Li, J.-M. (2009). Acta Cryst. E65, o1824. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, H. Q., Li, J. Z., Zhang, Y. & Zhang, D. (2008). Chin. J. Inorg. Chem. 24, 990–993. Web of Science CSD CrossRef CAS Google Scholar
Zhang, H.-Q., Li, J.-Z., Zhang, Y., Zhang, D. & Su, Z.-H. (2007). Acta Cryst. E63, o3536. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 6| June 2012| Page o1843

doi:10.1107/S1600536812020004

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

(4Z)-4-[(2-Chloro­anilino)(phen­yl)methyl­­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

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Experimental

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organic compounds

(4Z)-4-[(2-Chloroanilino)(phenyl)methylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one