3-Methyl-1-phenyl-4-[(phen-yl)(2-phenyl-hydrazin-1-yl)meth-ylidene]-1H-pyrazol-5(4H)-one.

The title compound, C(23)H(20)N(4)O, is a heterocyclic phenyl-hydrazone Schiff base with a pyrazole moiety. In the crystal, a variety of inter-actions occur, including N-H⋯π and π-π stacking between the phenyl ring of the phenyl-hydrazinyl group and its symmetry-generated equivalent [centroid-centroid distance = 3.6512 (7) Å].

Related literature

For related structures, see: Zhu et al. (2010 ▶, 2011 ▶); Goh et al. (2009 ▶). For general background to pyrazolo­nes and their applications, see: Yang et al. (2000 ▶); Konstanti­novic et al. (2008 ▶); Joshi et al. (2011 ▶); Turan-Zitouni et al. (2000 ▶). For the biological activities of hydrazone Schiff bases, see: Yadav et al. (2010 ▶); Ozdemir et al. (2008 ▶); Vicini et al. (2006 ▶); Jagadeesh et al. (2010 ▶); Walcourt et al. (2004 ▶) and for their catalytic abilities, see: Pouralimardan et al. (2007 ▶).

Experimental

Crystal data

C23H20N4O

M = 368.43

Monoclinic,

a = 8.6806 (2) Å

b = 20.4319 (4) Å

c = 10.6100 (2) Å

β = 99.713 (1)°

V = 1854.83 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 200 K

0.59 × 0.40 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: numerical (SADABS; Bruker, 2010 ▶) T min = 0.87, T max = 0.98

17965 measured reflections

4607 independent reflections

3891 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.108

S = 1.04

4607 reflections

262 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and ShelXle (Hübschle et al., 2011 ▶); molecular graphics: ORTEP-3 (Farrugia,1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812013463/zj2068sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013463/zj2068Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812013463/zj2068Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812013463/zj2068Isup4.cml

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

C23H20N4O	F(000) = 776
Mr = 368.43	Dx = 1.319 Mg m−3
Monoclinic, P21/c	Melting point: 464 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.6806 (2) Å	Cell parameters from 200 reflections
b = 20.4319 (4) Å	θ = 2.6–26.6°
c = 10.6100 (2) Å	µ = 0.08 mm−1
β = 99.713 (1)°	T = 200 K
V = 1854.83 (7) Å3	Block, yellow
Z = 4	0.59 × 0.40 × 0.22 mm

Bruker APEXII CCD diffractometer	4607 independent reflections
Radiation source: sealed tube	3891 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
Detector resolution: 8.3333 pixels mm-1	θmax = 28.3°, θmin = 2.4°
φ and ω scans	h = −11→11
Absorption correction: numerical (SADABS; Bruker, 2010)	k = −27→26
Tmin = 0.87, Tmax = 0.98	l = −14→14
17965 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0506P)2 + 0.492P] where P = (Fo2 + 2Fc2)/3
4607 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.17 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
O1	0.37112 (10)	−0.06816 (4)	0.56481 (8)	0.0415 (2)
N1	0.19594 (11)	−0.06784 (5)	0.37026 (8)	0.0317 (2)
N2	0.08885 (10)	−0.02411 (5)	0.30147 (9)	0.0326 (2)
N3	0.35993 (12)	0.04986 (5)	0.68161 (8)	0.0351 (2)
H3	0.3866 (18)	0.0073 (8)	0.6855 (14)	0.049 (4)*
N4	0.42974 (12)	0.09280 (5)	0.77706 (8)	0.0333 (2)
H4	0.529 (2)	0.0996 (8)	0.7705 (16)	0.055 (4)*
C1	0.27317 (13)	−0.04046 (6)	0.48275 (9)	0.0314 (2)
C2	0.21562 (12)	0.02578 (5)	0.48023 (9)	0.0301 (2)
C3	0.10127 (12)	0.03072 (5)	0.36586 (10)	0.0308 (2)
C4	−0.00114 (14)	0.08688 (6)	0.31689 (12)	0.0410 (3)
H4A	0.0612	0.1205	0.2829	0.062*
H4B	−0.048	0.1054	0.3868	0.062*
H4C	−0.084	0.0717	0.2488	0.062*
C5	0.27016 (12)	0.07110 (5)	0.57521 (9)	0.0295 (2)
C11	0.22094 (13)	−0.12928 (5)	0.31617 (10)	0.0318 (2)
C12	0.31193 (16)	−0.17665 (6)	0.38711 (12)	0.0422 (3)
H12	0.356	−0.1683	0.4738	0.051*
C13	0.33855 (19)	−0.23605 (7)	0.33154 (14)	0.0521 (3)
H13	0.4021	−0.268	0.3802	0.063*
C14	0.27385 (18)	−0.24925 (7)	0.20636 (14)	0.0516 (3)
H14	0.291	−0.2903	0.1692	0.062*
C15	0.18389 (16)	−0.20201 (7)	0.13574 (12)	0.0477 (3)
H15	0.1397	−0.2108	0.0493	0.057*
C16	0.15679 (14)	−0.14194 (6)	0.18873 (11)	0.0390 (3)
H16	0.0953	−0.1097	0.1389	0.047*
C21	0.23894 (12)	0.14208 (5)	0.56126 (10)	0.0316 (2)
C22	0.29871 (15)	0.17609 (6)	0.46630 (11)	0.0410 (3)
H22	0.3529	0.1533	0.4092	0.049*
C23	0.27886 (18)	0.24303 (7)	0.45546 (14)	0.0526 (4)
H23	0.3216	0.2665	0.3922	0.063*
C24	0.19696 (19)	0.27574 (7)	0.53651 (15)	0.0575 (4)
H24	0.1834	0.3218	0.5289	0.069*
C25	0.13434 (18)	0.24193 (7)	0.62892 (15)	0.0534 (4)
H25	0.0757	0.2647	0.683	0.064*
C26	0.15687 (14)	0.17513 (6)	0.64279 (12)	0.0401 (3)
H26	0.1164	0.1521	0.7078	0.048*
C31	0.40268 (12)	0.07932 (5)	0.90166 (9)	0.0275 (2)
C32	0.51420 (13)	0.09944 (5)	1.00413 (10)	0.0314 (2)
H32	0.6078	0.1197	0.989	0.038*
C33	0.48897 (14)	0.08995 (6)	1.12813 (10)	0.0348 (2)
H33	0.5649	0.1043	1.1978	0.042*
C34	0.35439 (14)	0.05974 (6)	1.15146 (10)	0.0364 (2)
H34	0.3384	0.0525	1.2368	0.044*
C35	0.24276 (13)	0.04011 (6)	1.04931 (11)	0.0359 (2)
H35	0.1497	0.0196	1.0651	0.043*
C36	0.26506 (13)	0.05003 (5)	0.92422 (10)	0.0314 (2)
H36	0.1873	0.037	0.8547	0.038*

	U11	U22	U33	U12	U13	U23
O1	0.0531 (5)	0.0408 (5)	0.0266 (4)	0.0052 (4)	−0.0043 (3)	−0.0013 (3)
N1	0.0352 (5)	0.0358 (5)	0.0233 (4)	−0.0036 (4)	0.0026 (3)	−0.0006 (3)
N2	0.0315 (4)	0.0386 (5)	0.0269 (4)	−0.0043 (4)	0.0028 (3)	0.0017 (4)
N3	0.0482 (6)	0.0343 (5)	0.0215 (4)	−0.0007 (4)	0.0023 (4)	−0.0021 (4)
N4	0.0386 (5)	0.0394 (5)	0.0217 (4)	−0.0079 (4)	0.0048 (4)	−0.0014 (4)
C1	0.0365 (5)	0.0374 (6)	0.0207 (4)	−0.0040 (4)	0.0056 (4)	−0.0008 (4)
C2	0.0332 (5)	0.0359 (5)	0.0218 (5)	−0.0031 (4)	0.0068 (4)	0.0012 (4)
C3	0.0295 (5)	0.0375 (6)	0.0261 (5)	−0.0053 (4)	0.0069 (4)	0.0019 (4)
C4	0.0387 (6)	0.0424 (6)	0.0394 (6)	0.0009 (5)	−0.0008 (5)	0.0016 (5)
C5	0.0316 (5)	0.0359 (5)	0.0224 (4)	−0.0033 (4)	0.0089 (4)	0.0011 (4)
C11	0.0338 (5)	0.0360 (5)	0.0268 (5)	−0.0089 (4)	0.0091 (4)	−0.0031 (4)
C12	0.0570 (7)	0.0376 (6)	0.0313 (6)	−0.0038 (5)	0.0048 (5)	−0.0010 (5)
C13	0.0703 (9)	0.0385 (7)	0.0465 (7)	0.0016 (6)	0.0069 (7)	−0.0017 (6)
C14	0.0616 (8)	0.0440 (7)	0.0502 (8)	−0.0049 (6)	0.0126 (6)	−0.0145 (6)
C15	0.0476 (7)	0.0586 (8)	0.0366 (6)	−0.0082 (6)	0.0065 (5)	−0.0175 (6)
C16	0.0371 (6)	0.0493 (7)	0.0304 (5)	−0.0048 (5)	0.0051 (4)	−0.0060 (5)
C21	0.0338 (5)	0.0342 (5)	0.0258 (5)	−0.0055 (4)	0.0022 (4)	−0.0003 (4)
C22	0.0480 (7)	0.0428 (7)	0.0318 (6)	−0.0101 (5)	0.0057 (5)	0.0034 (5)
C23	0.0622 (9)	0.0438 (7)	0.0465 (7)	−0.0173 (6)	−0.0060 (6)	0.0118 (6)
C24	0.0667 (9)	0.0340 (6)	0.0615 (9)	−0.0028 (6)	−0.0189 (7)	0.0021 (6)
C25	0.0573 (8)	0.0465 (7)	0.0519 (8)	0.0131 (6)	−0.0036 (6)	−0.0093 (6)
C26	0.0403 (6)	0.0444 (7)	0.0355 (6)	0.0027 (5)	0.0060 (5)	−0.0009 (5)
C31	0.0333 (5)	0.0267 (5)	0.0226 (4)	0.0014 (4)	0.0050 (4)	0.0004 (4)
C32	0.0326 (5)	0.0336 (5)	0.0276 (5)	−0.0032 (4)	0.0040 (4)	−0.0001 (4)
C33	0.0404 (6)	0.0378 (6)	0.0246 (5)	0.0008 (4)	0.0006 (4)	−0.0015 (4)
C34	0.0463 (6)	0.0387 (6)	0.0258 (5)	0.0029 (5)	0.0110 (4)	0.0029 (4)
C35	0.0374 (6)	0.0359 (6)	0.0367 (6)	−0.0030 (4)	0.0132 (4)	0.0021 (4)
C36	0.0334 (5)	0.0309 (5)	0.0293 (5)	−0.0029 (4)	0.0030 (4)	−0.0019 (4)

O1—C1	1.2456 (13)	C15—C16	1.3865 (18)
N1—C1	1.3844 (13)	C15—H15	0.95
N1—N2	1.4021 (13)	C16—H16	0.95
N1—C11	1.4123 (14)	C21—C26	1.3856 (16)
N2—C3	1.3072 (14)	C21—C22	1.3941 (15)
N3—C5	1.3316 (14)	C22—C23	1.381 (2)
N3—N4	1.3983 (13)	C22—H22	0.95
N3—H3	0.899 (16)	C23—C24	1.378 (2)
N4—C31	1.4084 (13)	C23—H23	0.95
N4—H4	0.887 (17)	C24—C25	1.383 (2)
C1—C2	1.4414 (16)	C24—H24	0.95
C2—C5	1.3915 (15)	C25—C26	1.3832 (19)
C2—C3	1.4358 (14)	C25—H25	0.95
C3—C4	1.4903 (16)	C26—H26	0.95
C4—H4A	0.98	C31—C32	1.3903 (14)
C4—H4B	0.98	C31—C36	1.3925 (15)
C4—H4C	0.98	C32—C33	1.3834 (15)
C5—C21	1.4782 (15)	C32—H32	0.95
C11—C12	1.3880 (17)	C33—C34	1.3801 (17)
C11—C16	1.3968 (15)	C33—H33	0.95
C12—C13	1.3856 (19)	C34—C35	1.3858 (16)
C12—H12	0.95	C34—H34	0.95
C13—C14	1.379 (2)	C35—C36	1.3881 (15)
C13—H13	0.95	C35—H35	0.95
C14—C15	1.380 (2)	C36—H36	0.95
C14—H14	0.95
C1—N1—N2	111.93 (9)	C14—C15—H15	119.4
C1—N1—C11	128.62 (9)	C16—C15—H15	119.4
N2—N1—C11	119.25 (9)	C15—C16—C11	119.29 (12)
C3—N2—N1	106.56 (9)	C15—C16—H16	120.4
C5—N3—N4	121.98 (10)	C11—C16—H16	120.4
C5—N3—H3	117.6 (10)	C26—C21—C22	120.10 (11)
N4—N3—H3	119.8 (10)	C26—C21—C5	121.36 (10)
N3—N4—C31	115.89 (9)	C22—C21—C5	118.50 (10)
N3—N4—H4	110.4 (11)	C23—C22—C21	119.83 (13)
C31—N4—H4	115.0 (11)	C23—C22—H22	120.1
O1—C1—N1	126.39 (11)	C21—C22—H22	120.1
O1—C1—C2	129.28 (10)	C24—C23—C22	119.92 (13)
N1—C1—C2	104.33 (9)	C24—C23—H23	120.0
C5—C2—C3	131.87 (10)	C22—C23—H23	120.0
C5—C2—C1	122.48 (10)	C23—C24—C25	120.39 (13)
C3—C2—C1	105.65 (9)	C23—C24—H24	119.8
N2—C3—C2	111.45 (10)	C25—C24—H24	119.8
N2—C3—C4	119.07 (10)	C26—C25—C24	120.19 (14)
C2—C3—C4	129.46 (10)	C26—C25—H25	119.9
C3—C4—H4A	109.5	C24—C25—H25	119.9
C3—C4—H4B	109.5	C25—C26—C21	119.52 (13)
H4A—C4—H4B	109.5	C25—C26—H26	120.2
C3—C4—H4C	109.5	C21—C26—H26	120.2
H4A—C4—H4C	109.5	C32—C31—C36	119.81 (9)
H4B—C4—H4C	109.5	C32—C31—N4	118.15 (9)
N3—C5—C2	118.43 (10)	C36—C31—N4	121.94 (9)
N3—C5—C21	118.41 (9)	C33—C32—C31	120.08 (10)
C2—C5—C21	123.10 (9)	C33—C32—H32	120.0
C12—C11—C16	119.55 (11)	C31—C32—H32	120.0
C12—C11—N1	120.79 (10)	C34—C33—C32	120.52 (10)
C16—C11—N1	119.64 (10)	C34—C33—H33	119.7
C13—C12—C11	120.03 (12)	C32—C33—H33	119.7
C13—C12—H12	120.0	C33—C34—C35	119.38 (10)
C11—C12—H12	120.0	C33—C34—H34	120.3
C14—C13—C12	120.75 (14)	C35—C34—H34	120.3
C14—C13—H13	119.6	C34—C35—C36	120.91 (10)
C12—C13—H13	119.6	C34—C35—H35	119.5
C13—C14—C15	119.17 (13)	C36—C35—H35	119.5
C13—C14—H14	120.4	C35—C36—C31	119.28 (10)
C15—C14—H14	120.4	C35—C36—H36	120.4
C14—C15—C16	121.20 (12)	C31—C36—H36	120.4
C1—N1—N2—C3	2.24 (12)	C11—C12—C13—C14	−0.9 (2)
C11—N1—N2—C3	−173.08 (9)	C12—C13—C14—C15	1.1 (2)
C5—N3—N4—C31	127.25 (11)	C13—C14—C15—C16	−0.5 (2)
N2—N1—C1—O1	177.77 (10)	C14—C15—C16—C11	−0.44 (19)
C11—N1—C1—O1	−7.46 (18)	C12—C11—C16—C15	0.69 (17)
N2—N1—C1—C2	−2.98 (11)	N1—C11—C16—C15	179.00 (10)
C11—N1—C1—C2	171.79 (10)	N3—C5—C21—C26	−64.01 (14)
O1—C1—C2—C5	2.00 (18)	C2—C5—C21—C26	118.77 (12)
N1—C1—C2—C5	−177.23 (9)	N3—C5—C21—C22	113.82 (12)
O1—C1—C2—C3	−178.25 (11)	C2—C5—C21—C22	−63.40 (14)
N1—C1—C2—C3	2.53 (11)	C26—C21—C22—C23	1.41 (18)
N1—N2—C3—C2	−0.47 (11)	C5—C21—C22—C23	−176.45 (11)
N1—N2—C3—C4	−179.01 (9)	C21—C22—C23—C24	−1.53 (19)
C5—C2—C3—N2	178.40 (10)	C22—C23—C24—C25	0.0 (2)
C1—C2—C3—N2	−1.33 (11)	C23—C24—C25—C26	1.6 (2)
C5—C2—C3—C4	−3.25 (19)	C24—C25—C26—C21	−1.7 (2)
C1—C2—C3—C4	177.03 (11)	C22—C21—C26—C25	0.22 (18)
N4—N3—C5—C2	174.74 (10)	C5—C21—C26—C25	178.02 (11)
N4—N3—C5—C21	−2.61 (15)	N3—N4—C31—C32	152.77 (10)
C3—C2—C5—N3	169.52 (11)	N3—N4—C31—C36	−30.79 (15)
C1—C2—C5—N3	−10.79 (15)	C36—C31—C32—C33	0.46 (16)
C3—C2—C5—C21	−13.26 (17)	N4—C31—C32—C33	176.98 (10)
C1—C2—C5—C21	166.43 (10)	C31—C32—C33—C34	0.88 (17)
C1—N1—C11—C12	13.08 (17)	C32—C33—C34—C35	−1.32 (18)
N2—N1—C11—C12	−172.48 (10)	C33—C34—C35—C36	0.44 (18)
C1—N1—C11—C16	−165.22 (11)	C34—C35—C36—C31	0.89 (17)
N2—N1—C11—C16	9.22 (15)	C32—C31—C36—C35	−1.33 (16)
C16—C11—C12—C13	−0.05 (19)	N4—C31—C36—C35	−177.71 (10)
N1—C11—C12—C13	−178.35 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.899 (16)	1.994 (16)	2.7204 (13)	136.9 (13)
C12—H12···O1	0.95	2.26	2.8993 (15)	124
C16—H16···N2	0.95	2.46	2.7950 (16)	100
C33—H33···O1i	0.95	2.59	3.3094 (13)	132
N4—H4···Cg2ii	0.887 (18)	2.728 (17)	3.5021 (12)	146.6 (14)

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯Cg2i	0.887 (18)	2.728 (17)	3.5021 (12)	146.6 (14)

Symmetry code: (i) .