3-Methyl-1-phenyl-4-[(Z)-phen­yl(4-acetamido­anilino)methyl­idene]-1H-pyrazol-5(4H)-one

Zhi, L.-H.; Wang, Y.

doi:10.1107/S1600536812026840

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2132

https://doi.org/10.1107/S1600536812026840

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3-Methyl-1-phenyl-4-[(Z)-phenyl(4-acetamidoanilino)methylidene]-1H-pyrazol-5(4H)-one

Li-Hua Zhi ^a and Yuan Wang ^a ^*

^aDepartment of Physics and Chemistry, Henan Polytechnic University, Jiaozuo 454000, People's Republic of China
^*Correspondence e-mail: wangyuan08@hpu.edu.cn

(Received 9 June 2012; accepted 13 June 2012; online 20 June 2012)

In the title compound, C₂₅H₂₂N₄O₂, the dihedral angles between the central pyrazole ring and the phenyl and benzene rings are 37.01 (3), 75.58 (7) and 49.67 (8)°. An intramolecular N—H⋯O hydrogen bond generates an S(6) motif. In the crystal, N—H⋯O hydrogen bonds link molecules into a zigzag chain extended along the b axis.

Related literature

For the synthesis of Schiff bases derived from 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone and the DNA binding properties of their transition metal complexes, see: Wang & Yang (2005 ). For the structure of (E,E)-3,3′-dimethyl-1,1′-diphenyl-4,4′-{[3-azapentane-1,5-diylbis(azanediyl)]-bis(phenylmethylidyne)}di-1H-pyrazol-5(4H)-one, see: Zhang et al. (2010 ).

Experimental

Crystal data

C₂₅H₂₂N₄O₂
M_r = 410.47
Monoclinic, P 2₁ /n
a = 7.1800 (4) Å
b = 11.0562 (7) Å
c = 27.3932 (16) Å
β = 95.138 (4)°
V = 2165.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.19 × 0.18 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.985, T_max = 0.988
19323 measured reflections
5168 independent reflections
3047 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.169
S = 1.02
5168 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O1ⁱ	0.86	2.05	2.874 (2)	161
N3—H3A⋯O1	0.86	1.96	2.696 (2)	143
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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: https://doi.org/10.1107/S1600536812026840/gk2501sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812026840/gk2501Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812026840/gk2501Isup3.cml

checkCIF report

Comment top

For our interest in coordination chemistry of the Schiff bases derived from 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone (PMBP) (Wang & Yang, 2005; Zhang et al., 2010), the crystal structure of the title compound was determined by X-ray diffraction analysis.

As shown in Fig. 1, in the title molecule , the dihedral angles between the central pyrazole ring (r.m.s. deviation = 0.0094 Å) and the other three benzene rings (C1—C6, r.m.s. deviation = 0.0047 Å, C12—C17, r.m.s. deviation = 0.0097 Å and C18—C23, r.m.s. deviation = 0.0033 Å) are 37.01 (3)°, 75.58 (7)° and 49.67 (8)°, respectively. A strong intramolecular N3—H3···O1 hydrogen bond forms a six-membered ring, producing a S(6) ring motif. In the crystal, intermolecular N—H···O hydrogen bonds link the molecules into a zigzag chain structure along the b axis (Table 1, Fig. 2).

Related literature top

For the synthesis of Schiff bases derived from 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone and the DNA binding properties of their transition metal complexes, see: Wang & Yang (2005). For the structure of (E,E)-3,3'-dimethyl-1,1'-diphenyl-4,4'-{[3-azapentane-1,5-diylbis(azanediyl)]-bis(phenylmethylidyne)}di-1H-pyrazol-5(4H)-one, see: Zhang et al. (2010).

Experimental top

1-Phenyl-3-methyl-4-benzoyl-5-pyrazolone (1.1 g, 4 mmol) was dissolved in EtOH (50 ml), and ethanolic solution (10 ml) containing N-(4-aminophenyl)acetylamide (0.6 g, 4 mmol) was added dropwise. The reaction mixture was refluxed on a water bath for 3 h, then cooled to room temperature. Yellow block crystals were obtained by slow evaporation of the reaction mixture.

Structure description top

For the synthesis of Schiff bases derived from 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone and the DNA binding properties of their transition metal complexes, see: Wang & Yang (2005). For the structure of (E,E)-3,3'-dimethyl-1,1'-diphenyl-4,4'-{[3-azapentane-1,5-diylbis(azanediyl)]-bis(phenylmethylidyne)}di-1H-pyrazol-5(4H)-one, see: Zhang et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 shown with 30% probability displacement ellipsoids.
	Fig. 2. Extended zigzag chain structure along the b axis formed by N—H···O hydrogen bonds [ symmetry code (i): 0.5 - x, y - 0.5, 0.5 - z]. Hydrogen bonds are shown as dashed lines and C-bound H atoms are omitted for clarity.

3-Methyl-1-phenyl-4-[(Z)-phenyl(4-acetamidoanilino)methylidene]- 1H-pyrazol-5(4H)-one top

Crystal data top

C₂₅H₂₂N₄O₂	F(000) = 864
M_r = 410.47	D_x = 1.259 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 567(9) K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.1800 (4) Å	Cell parameters from 3801 reflections
b = 11.0562 (7) Å	θ = 2.4–22.2°
c = 27.3932 (16) Å	µ = 0.08 mm⁻¹
β = 95.138 (4)°	T = 296 K
V = 2165.8 (2) Å³	Block, yellow
Z = 4	0.19 × 0.18 × 0.15 mm

Data collection top

Bruker APEXII CCD diffractometer	5168 independent reflections
Radiation source: fine-focus sealed tube	3047 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
φ and ω scans	θ_max = 27.9°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −9→9
T_min = 0.985, T_max = 0.988	k = −14→12
19323 measured reflections	l = −36→31

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.169	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0834P)² + 0.3021P] where P = (F_o² + 2F_c²)/3
5168 reflections	(Δ/σ)_max < 0.001
280 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₅H₂₂N₄O₂	V = 2165.8 (2) Å³
M_r = 410.47	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.1800 (4) Å	µ = 0.08 mm⁻¹
b = 11.0562 (7) Å	T = 296 K
c = 27.3932 (16) Å	0.19 × 0.18 × 0.15 mm
β = 95.138 (4)°

Data collection top

Bruker APEXII CCD diffractometer	5168 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	3047 reflections with I > 2σ(I)
T_min = 0.985, T_max = 0.988	R_int = 0.037
19323 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.169	H-atom parameters constrained
S = 1.02	Δρ_max = 0.18 e Å⁻³
5168 reflections	Δρ_min = −0.22 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
C1	1.1453 (4)	0.8096 (3)	0.15116 (9)	0.0775 (7)
H1A	1.2285	0.8712	0.1610	0.093*
C2	0.9601 (4)	0.8167 (2)	0.16072 (10)	0.0790 (7)
H2B	0.9189	0.8829	0.1777	0.095*
C3	0.8358 (3)	0.7268 (2)	0.14534 (8)	0.0648 (6)
H3B	0.7110	0.7325	0.1517	0.078*
C4	0.8971 (3)	0.62867 (18)	0.12057 (7)	0.0485 (5)
C5	1.0823 (3)	0.6204 (2)	0.11169 (8)	0.0600 (6)
H5A	1.1247	0.5535	0.0953	0.072*
C6	1.2045 (3)	0.7111 (2)	0.12710 (9)	0.0718 (7)
H6A	1.3295	0.7051	0.1210	0.086*
C7	0.6243 (3)	0.48691 (17)	0.12369 (7)	0.0464 (5)
C8	0.5483 (3)	0.39817 (17)	0.08929 (6)	0.0441 (5)
C9	0.6660 (3)	0.40227 (18)	0.04957 (7)	0.0498 (5)
C10	0.6607 (4)	0.3296 (2)	0.00387 (8)	0.0725 (7)
H10A	0.7596	0.3552	−0.0151	0.109*
H10B	0.5424	0.3410	−0.0148	0.109*
H10C	0.6766	0.2456	0.0121	0.109*
C11	0.4038 (3)	0.31978 (17)	0.09954 (6)	0.0447 (4)
C12	0.3277 (3)	0.22780 (18)	0.06380 (6)	0.0456 (5)
C13	0.3630 (3)	0.10682 (19)	0.07272 (8)	0.0581 (6)
H13A	0.4253	0.0827	0.1023	0.070*
C14	0.3063 (4)	0.0220 (2)	0.03798 (9)	0.0746 (7)
H14A	0.3336	−0.0593	0.0438	0.090*
C15	0.2096 (4)	0.0564 (3)	−0.00520 (9)	0.0771 (7)
H15A	0.1720	−0.0014	−0.0287	0.092*
C16	0.1685 (4)	0.1755 (3)	−0.01361 (8)	0.0719 (7)
H16A	0.0998	0.1984	−0.0425	0.086*
C17	0.2282 (3)	0.2620 (2)	0.02036 (7)	0.0617 (6)
H17A	0.2018	0.3432	0.0142	0.074*
C18	0.1978 (3)	0.25908 (17)	0.16386 (7)	0.0463 (5)
C19	0.2328 (3)	0.21907 (19)	0.21160 (7)	0.0498 (5)
H19A	0.3489	0.2333	0.2285	0.060*
C20	0.0977 (3)	0.15856 (18)	0.23422 (7)	0.0491 (5)
H20A	0.1231	0.1323	0.2664	0.059*
C21	−0.0763 (3)	0.13596 (17)	0.20977 (6)	0.0443 (4)
C22	−0.1115 (3)	0.17695 (19)	0.16203 (7)	0.0549 (5)
H22A	−0.2276	0.1631	0.1451	0.066*
C23	0.0252 (3)	0.2384 (2)	0.13947 (7)	0.0550 (5)
H23A	−0.0001	0.2660	0.1075	0.066*
C24	−0.3715 (3)	0.02447 (19)	0.21917 (8)	0.0542 (5)
C25	−0.4773 (3)	−0.0323 (2)	0.25790 (9)	0.0727 (7)
H25A	−0.5909	−0.0673	0.2430	0.109*
H25B	−0.5068	0.0283	0.2811	0.109*
H25C	−0.4021	−0.0942	0.2744	0.109*
O1	0.57427 (19)	0.51393 (13)	0.16510 (5)	0.0552 (4)
O2	−0.4273 (2)	0.02170 (19)	0.17623 (6)	0.0864 (6)
N1	0.7704 (2)	0.53743 (15)	0.10245 (6)	0.0514 (4)
N2	0.7976 (2)	0.48311 (15)	0.05741 (6)	0.0551 (5)
N3	0.3406 (2)	0.32684 (15)	0.14348 (5)	0.0518 (4)
H3A	0.3941	0.3806	0.1626	0.062*
N4	−0.2087 (2)	0.07663 (15)	0.23616 (5)	0.0512 (4)
H4A	−0.1822	0.0732	0.2674	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0842 (18)	0.0814 (18)	0.0656 (15)	−0.0301 (15)	−0.0001 (13)	−0.0072 (13)
C2	0.0926 (19)	0.0665 (16)	0.0795 (16)	−0.0165 (14)	0.0161 (14)	−0.0244 (13)
C3	0.0673 (14)	0.0582 (14)	0.0711 (14)	−0.0075 (11)	0.0183 (11)	−0.0156 (11)
C4	0.0577 (12)	0.0457 (12)	0.0431 (10)	−0.0046 (9)	0.0104 (9)	0.0010 (8)
C5	0.0606 (13)	0.0569 (14)	0.0638 (13)	−0.0006 (11)	0.0125 (11)	0.0008 (10)
C6	0.0555 (14)	0.0841 (18)	0.0753 (15)	−0.0111 (13)	0.0033 (12)	0.0061 (14)
C7	0.0548 (11)	0.0453 (11)	0.0406 (9)	0.0002 (9)	0.0130 (8)	0.0001 (8)
C8	0.0556 (11)	0.0415 (11)	0.0364 (9)	−0.0023 (9)	0.0103 (8)	−0.0021 (8)
C9	0.0648 (13)	0.0457 (11)	0.0412 (10)	−0.0044 (10)	0.0174 (9)	−0.0013 (8)
C10	0.0918 (17)	0.0774 (17)	0.0527 (12)	−0.0174 (14)	0.0322 (12)	−0.0193 (11)
C11	0.0527 (11)	0.0445 (11)	0.0376 (9)	0.0017 (9)	0.0076 (8)	0.0018 (8)
C12	0.0535 (11)	0.0477 (11)	0.0366 (9)	−0.0034 (9)	0.0103 (8)	0.0011 (8)
C13	0.0704 (14)	0.0509 (13)	0.0518 (11)	0.0013 (11)	−0.0013 (10)	0.0011 (10)
C14	0.0971 (19)	0.0516 (14)	0.0741 (16)	−0.0021 (13)	0.0011 (14)	−0.0119 (12)
C15	0.0907 (18)	0.0791 (19)	0.0612 (14)	−0.0218 (15)	0.0061 (13)	−0.0232 (13)
C16	0.0824 (17)	0.090 (2)	0.0408 (11)	−0.0137 (15)	−0.0053 (11)	0.0003 (12)
C17	0.0786 (15)	0.0601 (14)	0.0458 (11)	−0.0037 (12)	0.0027 (10)	0.0091 (10)
C18	0.0537 (12)	0.0461 (11)	0.0410 (10)	−0.0025 (9)	0.0143 (8)	−0.0015 (8)
C19	0.0500 (11)	0.0606 (13)	0.0391 (9)	−0.0010 (9)	0.0068 (8)	−0.0012 (9)
C20	0.0556 (12)	0.0570 (13)	0.0349 (9)	0.0007 (10)	0.0061 (8)	0.0057 (8)
C21	0.0516 (11)	0.0429 (11)	0.0392 (9)	−0.0005 (9)	0.0087 (8)	0.0020 (8)
C22	0.0566 (12)	0.0653 (14)	0.0429 (10)	−0.0089 (11)	0.0052 (9)	0.0079 (9)
C23	0.0600 (13)	0.0674 (14)	0.0375 (10)	−0.0052 (11)	0.0042 (9)	0.0098 (9)
C24	0.0538 (12)	0.0580 (13)	0.0509 (12)	−0.0018 (10)	0.0055 (9)	0.0094 (10)
C25	0.0667 (15)	0.0776 (17)	0.0745 (15)	−0.0185 (13)	0.0091 (12)	0.0209 (13)
O1	0.0633 (9)	0.0631 (9)	0.0418 (7)	−0.0091 (7)	0.0185 (6)	−0.0139 (6)
O2	0.0724 (11)	0.1269 (16)	0.0576 (10)	−0.0295 (11)	−0.0074 (8)	0.0188 (10)
N1	0.0626 (10)	0.0486 (10)	0.0458 (9)	−0.0102 (8)	0.0200 (8)	−0.0080 (7)
N2	0.0714 (11)	0.0540 (10)	0.0429 (9)	−0.0074 (9)	0.0226 (8)	−0.0058 (7)
N3	0.0621 (10)	0.0549 (10)	0.0404 (8)	−0.0136 (8)	0.0161 (7)	−0.0061 (7)
N4	0.0578 (10)	0.0577 (11)	0.0386 (8)	−0.0110 (9)	0.0070 (7)	0.0064 (7)

Geometric parameters (Å, º) top

C1—C6	1.361 (4)	C14—C15	1.371 (4)
C1—C2	1.380 (4)	C14—H14A	0.9300
C1—H1A	0.9300	C15—C16	1.365 (4)
C2—C3	1.376 (3)	C15—H15A	0.9300
C2—H2B	0.9300	C16—C17	1.376 (3)
C3—C4	1.373 (3)	C16—H16A	0.9300
C3—H3B	0.9300	C17—H17A	0.9300
C4—C5	1.376 (3)	C18—C23	1.374 (3)
C4—N1	1.418 (2)	C18—C19	1.382 (3)
C5—C6	1.374 (3)	C18—N3	1.424 (2)
C5—H5A	0.9300	C19—C20	1.371 (3)
C6—H6A	0.9300	C19—H19A	0.9300
C7—O1	1.256 (2)	C20—C21	1.386 (3)
C7—N1	1.364 (2)	C20—H20A	0.9300
C7—C8	1.434 (3)	C21—C22	1.386 (3)
C8—C11	1.399 (3)	C21—N4	1.407 (2)
C8—C9	1.437 (2)	C22—C23	1.384 (3)
C9—N2	1.304 (3)	C22—H22A	0.9300
C9—C10	1.485 (3)	C23—H23A	0.9300
C10—H10A	0.9600	C24—O2	1.209 (3)
C10—H10B	0.9600	C24—N4	1.348 (3)
C10—H10C	0.9600	C24—C25	1.497 (3)
C11—N3	1.326 (2)	C25—H25A	0.9600
C11—C12	1.482 (3)	C25—H25B	0.9600
C12—C13	1.379 (3)	C25—H25C	0.9600
C12—C17	1.385 (3)	N1—N2	1.401 (2)
C13—C14	1.372 (3)	N3—H3A	0.8600
C13—H13A	0.9300	N4—H4A	0.8600

C6—C1—C2	119.0 (2)	C16—C15—H15A	120.1
C6—C1—H1A	120.5	C14—C15—H15A	120.1
C2—C1—H1A	120.5	C15—C16—C17	120.5 (2)
C3—C2—C1	120.7 (2)	C15—C16—H16A	119.8
C3—C2—H2B	119.7	C17—C16—H16A	119.8
C1—C2—H2B	119.7	C16—C17—C12	119.8 (2)
C2—C3—C4	119.6 (2)	C16—C17—H17A	120.1
C2—C3—H3B	120.2	C12—C17—H17A	120.1
C4—C3—H3B	120.2	C23—C18—C19	119.12 (17)
C3—C4—C5	119.8 (2)	C23—C18—N3	123.15 (17)
C3—C4—N1	120.75 (18)	C19—C18—N3	117.60 (18)
C5—C4—N1	119.38 (18)	C20—C19—C18	120.51 (19)
C4—C5—C6	119.8 (2)	C20—C19—H19A	119.7
C4—C5—H5A	120.1	C18—C19—H19A	119.7
C6—C5—H5A	120.1	C19—C20—C21	120.86 (17)
C1—C6—C5	121.0 (2)	C19—C20—H20A	119.6
C1—C6—H6A	119.5	C21—C20—H20A	119.6
C5—C6—H6A	119.5	C22—C21—C20	118.52 (17)
O1—C7—N1	125.51 (18)	C22—C21—N4	124.24 (18)
O1—C7—C8	129.31 (17)	C20—C21—N4	117.18 (16)
N1—C7—C8	105.17 (15)	C21—C22—C23	120.34 (19)
C11—C8—C7	122.49 (15)	C21—C22—H22A	119.8
C11—C8—C9	131.94 (17)	C23—C22—H22A	119.8
C7—C8—C9	105.13 (16)	C18—C23—C22	120.64 (18)
N2—C9—C8	111.31 (16)	C18—C23—H23A	119.7
N2—C9—C10	118.23 (16)	C22—C23—H23A	119.7
C8—C9—C10	130.45 (19)	O2—C24—N4	123.28 (18)
C9—C10—H10A	109.5	O2—C24—C25	122.3 (2)
C9—C10—H10B	109.5	N4—C24—C25	114.45 (18)
H10A—C10—H10B	109.5	C24—C25—H25A	109.5
C9—C10—H10C	109.5	C24—C25—H25B	109.5
H10A—C10—H10C	109.5	H25A—C25—H25B	109.5
H10B—C10—H10C	109.5	C24—C25—H25C	109.5
N3—C11—C8	117.75 (17)	H25A—C25—H25C	109.5
N3—C11—C12	120.29 (16)	H25B—C25—H25C	109.5
C8—C11—C12	121.91 (15)	C7—N1—N2	111.92 (15)
C13—C12—C17	119.33 (19)	C7—N1—C4	129.48 (15)
C13—C12—C11	119.85 (18)	N2—N1—C4	118.51 (14)
C17—C12—C11	120.75 (18)	C9—N2—N1	106.42 (14)
C14—C13—C12	120.1 (2)	C11—N3—C18	129.94 (17)
C14—C13—H13A	119.9	C11—N3—H3A	115.0
C12—C13—H13A	119.9	C18—N3—H3A	115.0
C15—C14—C13	120.3 (2)	C24—N4—C21	128.81 (16)
C15—C14—H14A	119.8	C24—N4—H4A	115.6
C13—C14—H14A	119.8	C21—N4—H4A	115.6
C16—C15—C14	119.9 (2)

C6—C1—C2—C3	−1.3 (4)	C11—C12—C17—C16	176.10 (19)
C1—C2—C3—C4	0.5 (4)	C23—C18—C19—C20	0.6 (3)
C2—C3—C4—C5	0.6 (3)	N3—C18—C19—C20	176.74 (17)
C2—C3—C4—N1	−177.2 (2)	C18—C19—C20—C21	0.2 (3)
C3—C4—C5—C6	−0.8 (3)	C19—C20—C21—C22	−0.6 (3)
N1—C4—C5—C6	176.98 (19)	C19—C20—C21—N4	−178.09 (18)
C2—C1—C6—C5	1.0 (4)	C20—C21—C22—C23	0.3 (3)
C4—C5—C6—C1	0.1 (4)	N4—C21—C22—C23	177.62 (18)
O1—C7—C8—C11	−3.9 (3)	C19—C18—C23—C22	−0.9 (3)
N1—C7—C8—C11	174.95 (18)	N3—C18—C23—C22	−176.79 (18)
O1—C7—C8—C9	−177.1 (2)	C21—C22—C23—C18	0.4 (3)
N1—C7—C8—C9	1.7 (2)	O1—C7—N1—N2	176.45 (19)
C11—C8—C9—N2	−172.8 (2)	C8—C7—N1—N2	−2.4 (2)
C7—C8—C9—N2	−0.5 (2)	O1—C7—N1—C4	0.0 (3)
C11—C8—C9—C10	6.0 (4)	C8—C7—N1—C4	−178.89 (19)
C7—C8—C9—C10	178.3 (2)	C3—C4—N1—C7	−40.4 (3)
C7—C8—C11—N3	−2.1 (3)	C5—C4—N1—C7	141.8 (2)
C9—C8—C11—N3	169.1 (2)	C3—C4—N1—N2	143.3 (2)
C7—C8—C11—C12	−179.45 (18)	C5—C4—N1—N2	−34.5 (3)
C9—C8—C11—C12	−8.3 (3)	C8—C9—N2—N1	−1.0 (2)
N3—C11—C12—C13	−67.8 (3)	C10—C9—N2—N1	−179.88 (19)
C8—C11—C12—C13	109.5 (2)	C7—N1—N2—C9	2.2 (2)
N3—C11—C12—C17	115.0 (2)	C4—N1—N2—C9	179.07 (18)
C8—C11—C12—C17	−67.7 (3)	C8—C11—N3—C18	−179.58 (19)
C17—C12—C13—C14	2.6 (3)	C12—C11—N3—C18	−2.2 (3)
C11—C12—C13—C14	−174.6 (2)	C23—C18—N3—C11	−47.3 (3)
C12—C13—C14—C15	−1.9 (4)	C19—C18—N3—C11	136.7 (2)
C13—C14—C15—C16	−0.3 (4)	O2—C24—N4—C21	0.3 (4)
C14—C15—C16—C17	1.9 (4)	C25—C24—N4—C21	179.2 (2)
C15—C16—C17—C12	−1.2 (4)	C22—C21—N4—C24	16.4 (3)
C13—C12—C17—C16	−1.1 (3)	C20—C21—N4—C24	−166.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1ⁱ	0.86	2.05	2.874 (2)	161
N3—H3A···O1	0.86	1.96	2.696 (2)	143

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

Experimental details

Crystal data
Chemical formula	C₂₅H₂₂N₄O₂
M_r	410.47
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	7.1800 (4), 11.0562 (7), 27.3932 (16)
β (°)	95.138 (4)
V (Å³)	2165.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.19 × 0.18 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.985, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	19323, 5168, 3047
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.169, 1.02
No. of reflections	5168
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.22

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), 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
N4—H4A···O1ⁱ	0.86	2.05	2.874 (2)	161
N3—H3A···O1	0.86	1.96	2.696 (2)	143

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

Acknowledgements

The authors are grateful for financial support from the Natural Science Foundation of Henan Province (No.12B150011).

References

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Y. & Yang, Z.-Y. (2005). Transition Met. Chem. 30, 902–906. Web of Science CrossRef CAS Google Scholar
Zhang, Z.-P., Wang, Y., Li, X.-X. & Li, Y.-W. (2010). Acta Cryst. E66, o3326. Web of Science CSD CrossRef IUCr Journals Google Scholar

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

3-Methyl-1-phenyl-4-[(Z)-phen­yl(4-acetamido­anilino)methyl­­idene]-1H-pyrazol-5(4H)-one

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Experimental

Crystal data

Data collection

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organic compounds

3-Methyl-1-phenyl-4-[(Z)-phenyl(4-acetamidoanilino)methylidene]-1H-pyrazol-5(4H)-one