3-Methyl-1-phenyl-4-[(Z)-phen-yl(4-acetamido-anilino)methyl-idene]-1H-pyrazol-5(4H)-one.

In the title compound, C(25)H(22)N(4)O(2), 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 intra-molecular N-H⋯O hydrogen bond generates an S(6) motif. In the crystal, N-H⋯O hydrogen bonds link mol-ecules 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 = 410.47

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.169

S = 1.02

5168 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.22 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812026840/gk2501sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026840/gk2501Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812026840/gk2501Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H22N4O2	F(000) = 864
Mr = 410.47	Dx = 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

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

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(Fo2) + (0.0834P)2 + 0.3021P] where P = (Fo2 + 2Fc2)/3
5168 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .