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

Lu, R.; Xia, H.; Lü, X.; Zhao, S.

doi:10.1107/S1600536811037470

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2701

https://doi.org/10.1107/S1600536811037470

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

Rong Lu,^a ^* Hua Xia,^a Xingqiang Lü ^a and Shunsheng Zhao ^b

^aCollege of Chemical Engineering, Northwest University, Xi'an 710069, Shaanxi, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Xian University of Science and Technology, Xi'an 710054, Shaanxi, People's Republic of China
^*Correspondence e-mail: lu78441@yahoo.com.cn

(Received 17 July 2011; accepted 14 September 2011; online 30 September 2011)

The molecule of the title compound, C₂₃H₂₀N₄O, assumes a non-planar conformation in which the pyrazolone ring forms dihedral angles of 10.33 (11), 65.34 (11) and 63.52 (10)° with the three benzene rings. In the crystal, the molecules are linked by intermolecular N—H⋯N hydrogen bonds, generating chains parallel to the b axis. The secondary amino group is involved in an intramolecular N—H⋯O hydrogen bond.

Related literature

For the synthesis, properties and applications of the title compound, see: Hennig & Mann (1988 ); Bao et al. (2005 ).

Experimental

Crystal data

C₂₃H₂₀N₄O
M_r = 368.43
Monoclinic, P 2₁ /c
a = 9.200 (2) Å
b = 21.680 (5) Å
c = 9.608 (2) Å
β = 97.840 (4)°
V = 1898.4 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 273 K
0.30 × 0.20 × 0.20 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
9447 measured reflections
3369 independent reflections
1983 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.119
S = 0.94
3369 reflections
258 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1C⋯O1	0.96 (2)	1.93 (2)	2.733 (2)	139.8 (16)
N4—H4B⋯N2ⁱ	0.86	2.34	3.194 (2)	173
N4—H4A⋯N2ⁱⁱ	0.86	2.50	3.209 (2)	140
Symmetry codes: (i) x, y, z-1; (ii) -x+1, -y+1, -z+2.

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: https://doi.org/10.1107/S1600536811037470/fy2020sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811037470/fy2020Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811037470/fy2020Isup3.cml

checkCIF report

Comment top

The molecules of the title compound (Fig. 1) are linked by N—H···N hydrogen bonds, generating parallel chains as shown in Fig. 2. The aminophenyl rings protrude on both sides of these chains. Adjacent chains are linked by stacking interactions between the protruding rings. The distance between the ring centroids is 3.6953 (14) Å.

Related literature top

For the synthesis, properties and applications of the title compound, see: Hennig & Mann (1988); Bao et al. (2005).

Experimental top

The title compound was obtained according to the synthetic procedure of Hennig & Mann (1988). o-Phenylenediamine and 4-benzoyl-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one were refluxed for 2 h in a 1:1 ratio 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.

Structure description top

For the synthesis, properties and applications of the title compound, see: Hennig & Mann (1988); Bao et al. (2005).

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. Molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. Packing of (I), showing molecules connected by N—H···N hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonding have been omitted.
	Fig. 3. Packing of (I), showing assembly of molecules connected by stacking interaction.

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

Crystal data top

C₂₃H₂₀N₄O	F(000) = 776
M_r = 368.43	D_x = 1.289 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10250 reflections
a = 9.200 (2) Å	θ = 1.9–25.1°
b = 21.680 (5) Å	µ = 0.08 mm⁻¹
c = 9.608 (2) Å	T = 273 K
β = 97.840 (4)°	Block, orange
V = 1898.4 (7) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3369 independent reflections
Radiation source: fine-focus sealed tube	1983 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
thin–slice ω scans	θ_max = 25.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −8→10
T_min = 0.857, T_max = 1.000	k = −25→25
9447 measured reflections	l = −11→9

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ²(F_o²) + (0.0677P)²] where P = (F_o² + 2F_c²)/3
3369 reflections	(Δ/σ)_max < 0.001
258 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₃H₂₀N₄O	V = 1898.4 (7) Å³
M_r = 368.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.200 (2) Å	µ = 0.08 mm⁻¹
b = 21.680 (5) Å	T = 273 K
c = 9.608 (2) Å	0.30 × 0.20 × 0.20 mm
β = 97.840 (4)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3369 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	1983 reflections with I > 2σ(I)
T_min = 0.857, T_max = 1.000	R_int = 0.039
9447 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	Δρ_max = 0.20 e Å⁻³
3369 reflections	Δρ_min = −0.24 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
N1	0.34922 (16)	0.43731 (6)	1.14992 (14)	0.0474 (4)
O1	0.24396 (16)	0.42406 (6)	0.91531 (13)	0.0633 (4)
N2	0.40425 (17)	0.48648 (7)	1.23643 (14)	0.0496 (4)
N3	0.20658 (17)	0.53669 (7)	0.78768 (14)	0.0507 (5)
N4	0.30500 (17)	0.51166 (7)	0.53720 (16)	0.0606 (5)
H4A	0.3527	0.4993	0.6155	0.073*
H4B	0.3353	0.5021	0.4592	0.073*
C7	0.2924 (2)	0.45725 (8)	1.01684 (18)	0.0474 (5)
C8	0.30147 (19)	0.52375 (8)	1.02509 (17)	0.0439 (5)
C11	0.24301 (19)	0.56189 (8)	0.91417 (18)	0.0447 (5)
C6	0.3536 (2)	0.37681 (8)	1.20613 (19)	0.0484 (5)
C18	0.1294 (2)	0.56260 (8)	0.66247 (18)	0.0444 (5)
C23	0.1803 (2)	0.54668 (8)	0.53687 (18)	0.0437 (5)
C9	0.3752 (2)	0.53710 (8)	1.16249 (18)	0.0464 (5)
C12	0.2170 (2)	0.62851 (8)	0.93519 (19)	0.0463 (5)
C19	0.0030 (2)	0.59683 (9)	0.6613 (2)	0.0556 (5)
H19A	−0.0302	0.6068	0.7457	0.067*
C22	0.0969 (2)	0.56593 (8)	0.41134 (19)	0.0521 (5)
H22A	0.1273	0.5553	0.3261	0.063*
C20	−0.0747 (2)	0.61646 (9)	0.5361 (2)	0.0589 (6)
H20A	−0.1581	0.6407	0.5360	0.071*
C21	−0.0276 (2)	0.59984 (9)	0.4113 (2)	0.0560 (6)
H21A	−0.0812	0.6118	0.3265	0.067*
C10	0.4277 (2)	0.59724 (9)	1.2264 (2)	0.0634 (6)
H10A	0.4739	0.5905	1.3209	0.095*
H10B	0.3458	0.6247	1.2271	0.095*
H10C	0.4971	0.6152	1.1722	0.095*
C5	0.4291 (2)	0.36538 (10)	1.3386 (2)	0.0614 (6)
H5A	0.4777	0.3973	1.3905	0.074*
C1	0.2792 (3)	0.32924 (9)	1.1319 (2)	0.0670 (6)
H1A	0.2265	0.3365	1.0438	0.080*
C17	0.2816 (2)	0.67312 (9)	0.8609 (2)	0.0592 (6)
H17A	0.3417	0.6617	0.7949	0.071*
C14	0.0998 (3)	0.70835 (12)	1.0518 (3)	0.0808 (8)
H14A	0.0365	0.7202	1.1147	0.097*
C4	0.4318 (3)	0.30662 (12)	1.3930 (2)	0.0780 (7)
H4C	0.4834	0.2991	1.4815	0.094*
C16	0.2562 (3)	0.73473 (10)	0.8853 (3)	0.0779 (8)
H16A	0.3003	0.7646	0.8357	0.094*
C15	0.1671 (3)	0.75248 (12)	0.9814 (3)	0.0877 (9)
H15A	0.1526	0.7941	0.9985	0.105*
C2	0.2838 (3)	0.27058 (10)	1.1899 (3)	0.0884 (8)
H2B	0.2341	0.2385	1.1396	0.106*
C13	0.1247 (2)	0.64666 (10)	1.0308 (2)	0.0636 (6)
H13A	0.0797	0.6171	1.0806	0.076*
C3	0.3600 (3)	0.25895 (11)	1.3197 (3)	0.0867 (8)
H3B	0.3630	0.2194	1.3574	0.104*
H1C	0.220 (2)	0.4928 (10)	0.787 (2)	0.070 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0579 (11)	0.0482 (9)	0.0345 (9)	0.0048 (7)	0.0009 (7)	−0.0006 (7)
O1	0.0923 (11)	0.0558 (8)	0.0373 (8)	0.0027 (7)	−0.0070 (7)	−0.0063 (6)
N2	0.0593 (11)	0.0532 (9)	0.0348 (9)	0.0034 (8)	0.0009 (7)	−0.0044 (7)
N3	0.0710 (12)	0.0487 (10)	0.0317 (9)	0.0107 (8)	0.0045 (8)	0.0002 (7)
N4	0.0600 (12)	0.0826 (12)	0.0390 (9)	0.0162 (9)	0.0059 (8)	−0.0078 (8)
C7	0.0540 (13)	0.0530 (11)	0.0349 (11)	0.0074 (9)	0.0053 (9)	−0.0008 (9)
C8	0.0516 (12)	0.0470 (10)	0.0328 (10)	0.0056 (9)	0.0053 (9)	−0.0003 (8)
C11	0.0472 (12)	0.0533 (11)	0.0345 (11)	0.0033 (9)	0.0094 (9)	0.0002 (8)
C6	0.0535 (13)	0.0518 (11)	0.0412 (11)	0.0128 (9)	0.0107 (9)	0.0037 (9)
C18	0.0514 (12)	0.0450 (10)	0.0360 (11)	0.0013 (9)	0.0030 (9)	0.0020 (8)
C23	0.0496 (12)	0.0431 (10)	0.0374 (11)	−0.0043 (9)	0.0026 (9)	−0.0032 (8)
C9	0.0511 (12)	0.0519 (11)	0.0368 (11)	0.0043 (9)	0.0083 (9)	−0.0029 (9)
C12	0.0514 (13)	0.0478 (11)	0.0387 (10)	0.0043 (9)	0.0023 (9)	−0.0017 (8)
C19	0.0593 (14)	0.0597 (12)	0.0488 (13)	0.0046 (11)	0.0108 (10)	−0.0011 (9)
C22	0.0604 (14)	0.0598 (12)	0.0349 (11)	−0.0094 (11)	0.0021 (9)	0.0006 (9)
C20	0.0523 (14)	0.0586 (12)	0.0640 (15)	0.0066 (10)	0.0011 (11)	0.0047 (10)
C21	0.0582 (14)	0.0584 (12)	0.0479 (13)	−0.0035 (11)	−0.0058 (11)	0.0062 (10)
C10	0.0738 (15)	0.0611 (12)	0.0527 (13)	−0.0036 (11)	−0.0010 (11)	−0.0094 (10)
C5	0.0581 (14)	0.0749 (14)	0.0510 (13)	0.0100 (11)	0.0069 (11)	0.0136 (11)
C1	0.0972 (18)	0.0512 (12)	0.0512 (13)	0.0067 (12)	0.0052 (12)	−0.0013 (10)
C17	0.0594 (14)	0.0607 (13)	0.0559 (13)	−0.0024 (11)	0.0023 (11)	0.0036 (10)
C14	0.0823 (19)	0.0806 (17)	0.0775 (18)	0.0269 (14)	0.0038 (14)	−0.0240 (14)
C4	0.0871 (19)	0.0848 (17)	0.0628 (15)	0.0292 (14)	0.0128 (13)	0.0267 (14)
C16	0.0868 (19)	0.0544 (15)	0.0843 (18)	−0.0080 (12)	−0.0180 (15)	0.0113 (12)
C15	0.101 (2)	0.0552 (14)	0.097 (2)	0.0219 (15)	−0.0250 (17)	−0.0167 (15)
C2	0.143 (3)	0.0514 (14)	0.0723 (18)	0.0021 (14)	0.0209 (17)	−0.0010 (12)
C13	0.0708 (16)	0.0670 (13)	0.0543 (13)	0.0116 (11)	0.0137 (12)	−0.0078 (10)
C3	0.128 (2)	0.0603 (15)	0.0780 (18)	0.0322 (15)	0.0379 (17)	0.0195 (14)

Geometric parameters (Å, º) top

N1—C7	1.383 (2)	C22—H22A	0.9300
N1—N2	1.4031 (18)	C20—C21	1.377 (3)
N1—C6	1.417 (2)	C20—H20A	0.9300
O1—C7	1.2446 (19)	C21—H21A	0.9300
N2—C9	1.315 (2)	C10—H10A	0.9600
N3—C11	1.333 (2)	C10—H10B	0.9600
N3—C18	1.426 (2)	C10—H10C	0.9600
N3—H1C	0.96 (2)	C5—C4	1.376 (3)
N4—C23	1.376 (2)	C5—H5A	0.9300
N4—H4A	0.8600	C1—C2	1.387 (3)
N4—H4B	0.8600	C1—H1A	0.9300
C7—C8	1.446 (2)	C17—C16	1.381 (3)
C8—C11	1.397 (2)	C17—H17A	0.9300
C8—C9	1.429 (2)	C14—C15	1.368 (3)
C11—C12	1.482 (2)	C14—C13	1.377 (3)
C6—C1	1.381 (3)	C14—H14A	0.9300
C6—C5	1.387 (3)	C4—C3	1.369 (3)
C18—C19	1.378 (3)	C4—H4C	0.9300
C18—C23	1.396 (2)	C16—C15	1.371 (4)
C23—C22	1.402 (2)	C16—H16A	0.9300
C9—C10	1.493 (3)	C15—H15A	0.9300
C12—C17	1.383 (3)	C2—C3	1.368 (3)
C12—C13	1.390 (3)	C2—H2B	0.9300
C19—C20	1.380 (3)	C13—H13A	0.9300
C19—H19A	0.9300	C3—H3B	0.9300
C22—C21	1.361 (3)

C7—N1—N2	111.75 (13)	C21—C20—H20A	120.3
C7—N1—C6	128.99 (15)	C19—C20—H20A	120.3
N2—N1—C6	119.23 (14)	C22—C21—C20	120.38 (18)
C9—N2—N1	106.48 (13)	C22—C21—H21A	119.8
C11—N3—C18	129.94 (16)	C20—C21—H21A	119.8
C11—N3—H1C	113.5 (11)	C9—C10—H10A	109.5
C18—N3—H1C	115.6 (11)	C9—C10—H10B	109.5
C23—N4—H4A	120.0	H10A—C10—H10B	109.5
C23—N4—H4B	120.0	C9—C10—H10C	109.5
H4A—N4—H4B	120.0	H10A—C10—H10C	109.5
O1—C7—N1	126.42 (16)	H10B—C10—H10C	109.5
O1—C7—C8	129.15 (16)	C4—C5—C6	119.6 (2)
N1—C7—C8	104.43 (14)	C4—C5—H5A	120.2
C11—C8—C9	132.03 (16)	C6—C5—H5A	120.2
C11—C8—C7	122.34 (15)	C6—C1—C2	119.4 (2)
C9—C8—C7	105.62 (14)	C6—C1—H1A	120.3
N3—C11—C8	118.40 (16)	C2—C1—H1A	120.3
N3—C11—C12	119.89 (15)	C16—C17—C12	119.7 (2)
C8—C11—C12	121.68 (15)	C16—C17—H17A	120.2
C1—C6—C5	119.43 (18)	C12—C17—H17A	120.2
C1—C6—N1	120.54 (17)	C15—C14—C13	120.7 (2)
C5—C6—N1	120.00 (17)	C15—C14—H14A	119.6
C19—C18—C23	120.54 (17)	C13—C14—H14A	119.6
C19—C18—N3	122.79 (17)	C3—C4—C5	121.4 (2)
C23—C18—N3	116.40 (16)	C3—C4—H4C	119.3
N4—C23—C18	120.83 (16)	C5—C4—H4C	119.3
N4—C23—C22	121.65 (17)	C15—C16—C17	121.0 (2)
C18—C23—C22	117.49 (18)	C15—C16—H16A	119.5
N2—C9—C8	111.47 (15)	C17—C16—H16A	119.5
N2—C9—C10	118.43 (16)	C14—C15—C16	119.3 (2)
C8—C9—C10	130.00 (17)	C14—C15—H15A	120.3
C17—C12—C13	119.14 (18)	C16—C15—H15A	120.3
C17—C12—C11	121.51 (18)	C3—C2—C1	121.3 (2)
C13—C12—C11	119.35 (18)	C3—C2—H2B	119.4
C18—C19—C20	120.60 (19)	C1—C2—H2B	119.4
C18—C19—H19A	119.7	C14—C13—C12	120.1 (2)
C20—C19—H19A	119.7	C14—C13—H13A	120.0
C21—C22—C23	121.51 (19)	C12—C13—H13A	120.0
C21—C22—H22A	119.2	C2—C3—C4	118.8 (2)
C23—C22—H22A	119.2	C2—C3—H3B	120.6
C21—C20—C19	119.4 (2)	C4—C3—H3B	120.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1C···O1	0.96 (2)	1.93 (2)	2.733 (2)	139.8 (16)
N4—H4B···N2ⁱ	0.86	2.34	3.194 (2)	173
N4—H4A···N2ⁱⁱ	0.86	2.50	3.209 (2)	140

Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₀N₄O
M_r	368.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	9.200 (2), 21.680 (5), 9.608 (2)
β (°)	97.840 (4)
V (Å³)	1898.4 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector
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	9447, 3369, 1983
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.119, 0.94
No. of reflections	3369
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)	0.20, −0.24

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—H1C···O1	0.96 (2)	1.93 (2)	2.733 (2)	139.8 (16)
N4—H4B···N2ⁱ	0.86	2.34	3.194 (2)	173.4
N4—H4A···N2ⁱⁱ	0.86	2.50	3.209 (2)	140.3

Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z+2.

Acknowledgements

This project was supported by the Natural Science Basic Research Plan in Shaanxi Province of China (program Nos 2010JM2006 and 2011JQ2011) and the Scientific Research Program funded by the Shaanxi Provincial Education Department (program No. 2008 J K440).

References

Bao, F., Ma, R., Lv, X. Q., Gui, G. Q. & Wu, Q. (2005). Appl. Organomet. Chem. 20, 32–38. Web of Science CSD CrossRef Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hennig, L. & Mann, G. (1988). Z. Chem. 28, 364–365. CrossRef CAS 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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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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