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

Zou, D.; Lü, X.; Zhao, S.; Liu, X.

doi:10.1107/S160053681204086X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3148

doi:10.1107/S160053681204086X

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

Dan Zou,^a Xingqiang Lü,^a Shunsheng Zhao ^b and Xiangrong Liu ^b ^*

^aCollege of Chemical Engineering, Northwest University, Xi'an 710069, Shannxi, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Xian University of Science and Technology, Xi'an 710054, Shannxi, People's Republic of China
^*Correspondence e-mail: lvxq@nwu.edu.cn

(Received 1 August 2012; accepted 28 September 2012; online 20 October 2012)

The molecule of the title compound, C₂₃H₁₈Cl₂N₄O, assumes a non-planar conformation in which the pyrazolone ring forms dihedral angles of 32.61 (19), 76.73 (14) and 52.57 (19)° with the three benzene rings. The secondary amino group is involved in an intramolecular N—H⋯O hydrogen bond. In the crystal, molecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers. An offset stacking interaction is observed between the chloro-substituted benzene rings protruding on both sides of these dimers [centroid–centroid distance = 3.862 (1) Å].

Related literature

For related structures, see: Lu et al. (2011 ). For bond-length data, see: Allen et al. (1987 ). For the catalytic properties of asymmetric Schiff bases, see: Caboni et al. (2012 ). For the synthesis, see: Hennig & Mann (1988 ).

Experimental

Crystal data

C₂₃H₁₈Cl₂N₄O
M_r = 437.31
Triclinic, $[P \overline 1]$
a = 8.0653 (16) Å
b = 10.931 (2) Å
c = 13.851 (3) Å
α = 111.627 (3)°
β = 90.775 (3)°
γ = 110.226 (3)°
V = 1051.1 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 296 K
0.30 × 0.21 × 0.18 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.857, T_max = 1.000
5308 measured reflections
3688 independent reflections
1992 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.189
S = 1.03
3688 reflections
280 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1	0.86	2.01	2.735 (4)	141
N4—H4B⋯O1ⁱ	0.88 (2)	2.18 (2)	3.022 (5)	162 (4)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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 and local programs.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681204086X/fy2067sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681204086X/fy2067Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681204086X/fy2067Isup3.cml

checkCIF report

Comment top

Asymmetrical Schiff bases are of interest due to their catalytic activity and the selectivity of their transition metal complexes in various reactions. Several asymmetrical Schiff base ligands and their transition metal complexes have been synthesized and studied. Here we report the crystal structure of a novel asymmetrical Schiff base ligand (Fig. 1). Bond lengths of the compound are in the range of normal values (Allen et al., 1987) and are comparable to those observed in similar compounds (Lu et al., 2011). The molecules are linked by N—H···O hydrogen bonds and stacking interaction, as shown in Fig. 2. The distance between the centroids of adjacent rings (C18 to C23, x, y, z and -x + 2, -y + 1, -z + 1) is 3.862 (1) Å.

Related literature top

For related structures, see: Lu et al. (2011). For bond-length data, see: Allen et al. (1987). For the catalytic properties of asymmetric Schiff bases, see: Caboni et al. (2012). For the synthesis, see: Hennig & Mann (1988).

Experimental top

The title compound was obtained according to the synthetic procedure of Hennig & Mann (1988) with some modification. 1,2-diamino-4,5-dichlorobenzene and 4-benzoyl-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one were refluxed for 2 h in a molar ratio of 1:1 in absolute ethanol to give the product. The single-crystal suitble for X-ray diffraction was obtained by slow evaporation of the ethanolic solution of the title compound.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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) and local programs.

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), showing molecules connected by hydrogen bonds (dashed lines) and stacking interaction. H atoms not involved in hydrogen bonding have been omitted.

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

Crystal data top

C₂₃H₁₈Cl₂N₄O	Z = 2
M_r = 437.31	F(000) = 452
Triclinic, P1	D_x = 1.382 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0653 (16) Å	Cell parameters from 3250 reflections
b = 10.931 (2) Å	θ = 1.8–25.2°
c = 13.851 (3) Å	µ = 0.33 mm⁻¹
α = 111.627 (3)°	T = 296 K
β = 90.775 (3)°	Block, red
γ = 110.226 (3)°	0.30 × 0.21 × 0.18 mm
V = 1051.1 (4) Å³

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3688 independent reflections
Radiation source: fine-focus sealed tube	1992 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
thin–slice ω scans	θ_max = 25.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→7
T_min = 0.857, T_max = 1.000	k = −13→12
5308 measured reflections	l = −15→16

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.189	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0881P)²] where P = (F_o² + 2F_c²)/3
3688 reflections	(Δ/σ)_max < 0.001
280 parameters	Δρ_max = 0.51 e Å⁻³
2 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₂₃H₁₈Cl₂N₄O	γ = 110.226 (3)°
M_r = 437.31	V = 1051.1 (4) Å³
Triclinic, P1	Z = 2
a = 8.0653 (16) Å	Mo Kα radiation
b = 10.931 (2) Å	µ = 0.33 mm⁻¹
c = 13.851 (3) Å	T = 296 K
α = 111.627 (3)°	0.30 × 0.21 × 0.18 mm
β = 90.775 (3)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3688 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	1992 reflections with I > 2σ(I)
T_min = 0.857, T_max = 1.000	R_int = 0.027
5308 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	2 restraints
wR(F²) = 0.189	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.51 e Å⁻³
3688 reflections	Δρ_min = −0.45 e Å⁻³
280 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
Cl2	1.11130 (17)	0.22914 (15)	0.36132 (9)	0.0878 (5)
Cl1	1.18254 (17)	0.24718 (17)	0.59173 (10)	0.0939 (5)
O1	0.5427 (3)	0.6431 (3)	0.7490 (2)	0.0541 (7)
N2	0.2712 (4)	0.4857 (3)	0.8999 (2)	0.0573 (9)
N3	0.6743 (4)	0.4320 (3)	0.6750 (2)	0.0498 (8)
H3A	0.6612	0.5073	0.6759	0.060*
N1	0.3415 (4)	0.5927 (3)	0.8613 (2)	0.0511 (8)
C19	0.9177 (5)	0.3465 (4)	0.6293 (3)	0.0503 (10)
H19A	0.9434	0.3579	0.6985	0.060*
C22	0.8476 (5)	0.3187 (4)	0.4243 (3)	0.0502 (10)
H22A	0.8266	0.3111	0.3558	0.060*
C18	0.7801 (5)	0.3803 (4)	0.6009 (3)	0.0433 (9)
C9	0.3620 (5)	0.4033 (4)	0.8684 (3)	0.0532 (10)
C6	0.2573 (5)	0.6900 (4)	0.8746 (3)	0.0482 (9)
C23	0.7409 (5)	0.3646 (4)	0.4970 (3)	0.0451 (9)
C11	0.5925 (5)	0.3812 (4)	0.7431 (3)	0.0444 (9)
C7	0.4691 (5)	0.5709 (4)	0.8000 (3)	0.0455 (9)
C20	1.0185 (5)	0.2954 (4)	0.5552 (3)	0.0526 (10)
C12	0.6100 (5)	0.2515 (4)	0.7451 (3)	0.0459 (9)
N4	0.6018 (5)	0.3963 (4)	0.4673 (3)	0.0624 (10)
C8	0.4918 (5)	0.4480 (4)	0.8058 (3)	0.0444 (9)
C21	0.9834 (5)	0.2847 (4)	0.4539 (3)	0.0538 (10)
C13	0.7013 (5)	0.2581 (4)	0.8339 (3)	0.0537 (10)
H13A	0.7464	0.3428	0.8934	0.064*
C5	0.0782 (6)	0.6554 (5)	0.8833 (3)	0.0607 (11)
H5A	0.0107	0.5666	0.8825	0.073*
C1	0.3573 (6)	0.8244 (4)	0.8808 (3)	0.0623 (11)
H1A	0.4793	0.8504	0.8782	0.075*
C17	0.5389 (5)	0.1236 (4)	0.6589 (3)	0.0625 (11)
H17A	0.4743	0.1174	0.6000	0.075*
C15	0.6556 (7)	0.0121 (5)	0.7463 (4)	0.0749 (14)
H15A	0.6714	−0.0683	0.7462	0.090*
C10	0.3125 (6)	0.2748 (4)	0.8947 (4)	0.0731 (14)
H10A	0.2210	0.2745	0.9383	0.110*
H10B	0.4161	0.2775	0.9316	0.110*
H10C	0.2687	0.1904	0.8310	0.110*
C4	−0.0012 (6)	0.7519 (6)	0.8933 (3)	0.0719 (13)
H4C	−0.1228	0.7268	0.8969	0.086*
C2	0.2773 (7)	0.9199 (5)	0.8910 (4)	0.0775 (14)
H2B	0.3445	1.0095	0.8932	0.093*
C14	0.7249 (6)	0.1390 (5)	0.8336 (4)	0.0668 (12)
H14A	0.7879	0.1441	0.8926	0.080*
C16	0.5628 (6)	0.0062 (5)	0.6596 (4)	0.0753 (13)
H16A	0.5157	−0.0789	0.6006	0.090*
C3	0.0976 (8)	0.8833 (6)	0.8979 (4)	0.0811 (15)
H3B	0.0442	0.9486	0.9057	0.097*
H4A	0.508 (4)	0.381 (4)	0.495 (3)	0.062 (13)*
H4B	0.572 (6)	0.371 (5)	0.3997 (17)	0.092 (17)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl2	0.0813 (9)	0.1355 (12)	0.0620 (7)	0.0711 (9)	0.0337 (6)	0.0267 (7)
Cl1	0.0773 (9)	0.1571 (13)	0.0793 (9)	0.0818 (9)	0.0190 (7)	0.0461 (9)
O1	0.0631 (17)	0.0617 (17)	0.0604 (17)	0.0372 (14)	0.0316 (13)	0.0354 (14)
N2	0.070 (2)	0.059 (2)	0.060 (2)	0.0348 (19)	0.0336 (17)	0.0300 (17)
N3	0.062 (2)	0.058 (2)	0.0479 (19)	0.0391 (17)	0.0273 (16)	0.0249 (16)
N1	0.057 (2)	0.0536 (19)	0.058 (2)	0.0311 (17)	0.0300 (16)	0.0295 (16)
C19	0.053 (2)	0.059 (2)	0.043 (2)	0.026 (2)	0.0123 (18)	0.0201 (19)
C22	0.048 (2)	0.065 (3)	0.041 (2)	0.026 (2)	0.0137 (18)	0.0214 (19)
C18	0.044 (2)	0.048 (2)	0.046 (2)	0.0230 (18)	0.0170 (17)	0.0215 (17)
C9	0.067 (3)	0.056 (2)	0.051 (2)	0.032 (2)	0.028 (2)	0.027 (2)
C6	0.056 (3)	0.056 (2)	0.045 (2)	0.035 (2)	0.0187 (18)	0.0200 (19)
C23	0.049 (2)	0.048 (2)	0.043 (2)	0.0229 (19)	0.0135 (17)	0.0178 (18)
C11	0.046 (2)	0.051 (2)	0.040 (2)	0.0218 (19)	0.0120 (17)	0.0200 (18)
C7	0.046 (2)	0.051 (2)	0.045 (2)	0.0242 (19)	0.0168 (18)	0.0194 (18)
C20	0.046 (2)	0.066 (3)	0.051 (2)	0.031 (2)	0.0133 (19)	0.020 (2)
C12	0.047 (2)	0.046 (2)	0.049 (2)	0.0238 (19)	0.0154 (18)	0.0182 (19)
N4	0.060 (3)	0.088 (3)	0.067 (3)	0.047 (2)	0.021 (2)	0.042 (2)
C8	0.057 (2)	0.047 (2)	0.042 (2)	0.0327 (19)	0.0211 (18)	0.0192 (17)
C21	0.045 (2)	0.064 (3)	0.053 (2)	0.025 (2)	0.0189 (19)	0.019 (2)
C13	0.067 (3)	0.052 (2)	0.047 (2)	0.028 (2)	0.012 (2)	0.0184 (19)
C5	0.060 (3)	0.065 (3)	0.057 (3)	0.030 (2)	0.018 (2)	0.018 (2)
C1	0.061 (3)	0.065 (3)	0.073 (3)	0.034 (2)	0.024 (2)	0.031 (2)
C17	0.069 (3)	0.058 (3)	0.055 (3)	0.025 (2)	0.018 (2)	0.016 (2)
C15	0.109 (4)	0.071 (3)	0.087 (4)	0.064 (3)	0.056 (3)	0.046 (3)
C10	0.093 (4)	0.066 (3)	0.088 (3)	0.043 (3)	0.051 (3)	0.048 (3)
C4	0.059 (3)	0.098 (4)	0.064 (3)	0.047 (3)	0.019 (2)	0.021 (3)
C2	0.098 (4)	0.076 (3)	0.083 (3)	0.054 (3)	0.037 (3)	0.037 (3)
C14	0.085 (3)	0.078 (3)	0.067 (3)	0.053 (3)	0.032 (2)	0.039 (3)
C16	0.096 (4)	0.048 (3)	0.075 (3)	0.029 (3)	0.032 (3)	0.015 (2)
C3	0.110 (4)	0.103 (4)	0.066 (3)	0.080 (4)	0.033 (3)	0.035 (3)

Geometric parameters (Å, º) top

Cl2—C21	1.724 (4)	C12—C17	1.380 (5)
Cl1—C20	1.716 (4)	C12—C13	1.391 (5)
O1—C7	1.254 (4)	N4—H4A	0.850 (18)
N2—C9	1.309 (4)	N4—H4B	0.876 (19)
N2—N1	1.409 (4)	C13—C14	1.378 (5)
N3—C11	1.336 (4)	C13—H13A	0.9300
N3—C18	1.424 (4)	C5—C4	1.380 (5)
N3—H3A	0.8600	C5—H5A	0.9300
N1—C7	1.372 (4)	C1—C2	1.374 (5)
N1—C6	1.409 (4)	C1—H1A	0.9300
C19—C18	1.379 (5)	C17—C16	1.365 (5)
C19—C20	1.394 (5)	C17—H17A	0.9300
C19—H19A	0.9300	C15—C16	1.375 (6)
C22—C21	1.374 (5)	C15—C14	1.380 (6)
C22—C23	1.398 (5)	C15—H15A	0.9300
C22—H22A	0.9300	C10—H10A	0.9600
C18—C23	1.404 (5)	C10—H10B	0.9600
C9—C8	1.439 (5)	C10—H10C	0.9600
C9—C10	1.502 (5)	C4—C3	1.357 (7)
C6—C1	1.379 (5)	C4—H4C	0.9300
C6—C5	1.380 (5)	C2—C3	1.378 (7)
C23—N4	1.381 (5)	C2—H2B	0.9300
C11—C8	1.382 (5)	C14—H14A	0.9300
C11—C12	1.482 (5)	C16—H16A	0.9300
C7—C8	1.448 (5)	C3—H3B	0.9300
C20—C21	1.380 (5)

C9—N2—N1	105.9 (3)	C11—C8—C7	122.6 (3)
C11—N3—C18	129.7 (3)	C9—C8—C7	104.5 (3)
C11—N3—H3A	115.2	C22—C21—C20	121.3 (3)
C18—N3—H3A	115.2	C22—C21—Cl2	118.2 (3)
C7—N1—C6	128.5 (3)	C20—C21—Cl2	120.5 (3)
C7—N1—N2	112.0 (3)	C14—C13—C12	119.9 (4)
C6—N1—N2	118.6 (3)	C14—C13—H13A	120.1
C18—C19—C20	120.5 (3)	C12—C13—H13A	120.1
C18—C19—H19A	119.7	C6—C5—C4	120.3 (4)
C20—C19—H19A	119.7	C6—C5—H5A	119.8
C21—C22—C23	120.2 (3)	C4—C5—H5A	119.8
C21—C22—H22A	119.9	C2—C1—C6	120.1 (4)
C23—C22—H22A	119.9	C2—C1—H1A	119.9
C19—C18—C23	120.3 (3)	C6—C1—H1A	119.9
C19—C18—N3	121.7 (3)	C16—C17—C12	120.4 (4)
C23—C18—N3	118.0 (3)	C16—C17—H17A	119.8
N2—C9—C8	112.2 (3)	C12—C17—H17A	119.8
N2—C9—C10	118.4 (3)	C16—C15—C14	119.1 (4)
C8—C9—C10	129.3 (3)	C16—C15—H15A	120.4
C1—C6—C5	119.1 (4)	C14—C15—H15A	120.4
C1—C6—N1	119.1 (4)	C9—C10—H10A	109.5
C5—C6—N1	121.8 (4)	C9—C10—H10B	109.5
N4—C23—C22	120.6 (3)	H10A—C10—H10B	109.5
N4—C23—C18	120.7 (3)	C9—C10—H10C	109.5
C22—C23—C18	118.6 (3)	H10A—C10—H10C	109.5
N3—C11—C8	119.3 (3)	H10B—C10—H10C	109.5
N3—C11—C12	117.7 (3)	C3—C4—C5	120.2 (4)
C8—C11—C12	123.0 (3)	C3—C4—H4C	119.9
O1—C7—N1	125.3 (3)	C5—C4—H4C	119.9
O1—C7—C8	129.5 (3)	C1—C2—C3	120.2 (5)
N1—C7—C8	105.2 (3)	C1—C2—H2B	119.9
C21—C20—C19	119.0 (3)	C3—C2—H2B	119.9
C21—C20—Cl1	121.7 (3)	C13—C14—C15	120.5 (4)
C19—C20—Cl1	119.3 (3)	C13—C14—H14A	119.8
C17—C12—C13	119.1 (3)	C15—C14—H14A	119.8
C17—C12—C11	120.8 (3)	C17—C16—C15	120.9 (4)
C13—C12—C11	120.0 (3)	C17—C16—H16A	119.5
C23—N4—H4A	120 (3)	C15—C16—H16A	119.5
C23—N4—H4B	117 (3)	C4—C3—C2	120.0 (4)
H4A—N4—H4B	110 (4)	C4—C3—H3B	120.0
C11—C8—C9	131.6 (3)	C2—C3—H3B	120.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.86	2.01	2.735 (4)	141
N4—H4B···O1ⁱ	0.88 (2)	2.18 (2)	3.022 (5)	162 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₈Cl₂N₄O
M_r	437.31
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.0653 (16), 10.931 (2), 13.851 (3)
α, β, γ (°)	111.627 (3), 90.775 (3), 110.226 (3)
V (Å³)	1051.1 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.30 × 0.21 × 0.18

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.857, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5308, 3688, 1992
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.189, 1.03
No. of reflections	3688
No. of parameters	280
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)	0.51, −0.45

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and local programs.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.86	2.01	2.735 (4)	141.3
N4—H4B···O1ⁱ	0.876 (19)	2.18 (2)	3.022 (5)	162 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The project was supported by the National Natural Science Foundation of China (program Nos. 21103135 and 21073139), the Natural Science Basic Research Plan in Shaanxi Province of China (program No. 2011JQ2011) and the Scientific Research Program Funded by Shaanxi Provincial Education Department (program No.12 J K0622).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc., Perkin Trans. 2, pp. S1–S19. Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Caboni, L., Kinsella, G. K., Blanco, F., Fayne, D., Jagoe, W. N., Carr, M., Williams, D. C., Meegan, M. J. & Lloyd, D. G. (2012). J. Med. Chem. 55, 1635–1644. Web of Science CrossRef CAS PubMed Google Scholar
Hennig, L. & Mann, G. (1988). Z. Chem. 28, 364–365. CrossRef CAS Google Scholar
Lu, R., Xia, H., Lü, X. & Zhao, S. (2011). Acta Cryst. E67, o2701. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2004). 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

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Volume 68| Part 11| November 2012| Page o3148

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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