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

Sharma, N.; Vyas, K.M.; Jadeja, R.N.; Kant, R.; Gupta, V.K.

doi:10.1107/S1600536812040330

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o3036

https://doi.org/10.1107/S1600536812040330

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

Naresh Sharma,^a Komal M. Vyas,^b R. N. Jadeja,^b Rajni Kant ^a and Vivek K. Gupta ^a ^*

^aPost-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and ^bDepartment of Chemistry, Faculty of Science, The M. S. University of Baroda, Vadodara 390 002, India
^*Correspondence e-mail: vivek_gupta2k2@hotmail.com

(Received 17 September 2012; accepted 24 September 2012; online 29 September 2012)

In the title molecule, C₂₅H₂₃N₃O₂, the pyrazole ring forms dihedral angles of 28.56 (7), 80.35 (7) and 31.99 (7)° with the phenyl ring, the p-tolyl ring and the p-tolylamino ring, respectively. The N—H group attached to the exocyclic C=C bond is in a syn arrangement with respect to the C=O bond of the pyrazolone group and an intramolecular N—H⋯O hydrogen bond is observed. In the crystal, weak C—H⋯π interactions link molecules along [100].

Related literature

For related structures, see: Vyas et al. (2011 ); Ma et al. (2006 ); Sun et al. (2007 ).

Experimental

Crystal data

C₂₅H₂₃N₃O
M_r = 381.46
Monoclinic, P 2₁ /n
a = 9.2694 (4) Å
b = 18.3156 (8) Å
c = 12.6716 (7) Å
β = 105.124 (5)°
V = 2076.80 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.30 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.914, T_max = 1.000
9542 measured reflections
4077 independent reflections
2343 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.132
S = 1.01
4077 reflections
270 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C7–C12 ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N21—H21⋯O5	0.99 (2)	1.82 (2)	2.702 (2)	146.4 (17)
C15—H15⋯Cgⁱ	0.93	2.63	3.470 (2)	152
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812040330/lh5535sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812040330/lh5535Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812040330/lh5535Isup3.cml

checkCIF report

Comment top

The title compound (I) was prepared as a continuation of our studies of the structures 4-toluoyl pyrazolones (Vyas et al., 2011). The molecular structure of (I) is shown in Fig 1. The bond lengths and angles in (I) are normal and correspond to those observed in related structures (Ma et al., 2006; Sun et al., 2007). The pyrazolone ring forms dihedral angles of 28.56 (7)°, 80.35 (7)° and 31.99 (7)° with the phenyl ring (C7—C12) and two benzene rings (C14—C19 and C22—C27). In The N—H group attached to the exocyclic C═C bond (C4-C13) is in a syn arrangement with respect to the C═O bond of the pyrazolone group and an intramolecular N—H···O hydrogen bond is observed. In the crystal, a weak C—H···π interaction link molecules along [100] (Fig .2).

Related literature top

For related structures, see: Vyas et al. (2011); Ma et al. (2006); Sun et al. (2007).

Experimental top

Equimolar (10 mmol) ethanolic solution (50 ml) of 5-Methyl-4-(4-methyl-benzoyl)-2-phenyl-2,4-dihydro-pyrazol-3-one and p-toluidine was refluxed for 6 h in round bottom flask, whereupon a microcrystalline yellow precipitate appeared. The product was then isolated and recrystallized from ethanol, and then dried in vacuo to give the title compound in 85% yield. Yellow single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution of the title compound.

Structure description top

For related structures, see: Vyas et al. (2011); Ma et al. (2006); Sun et al. (2007).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with ellipsoids are drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii. The dashed line indicates a hydrogen bond.
	Fig. 2. Part of the one-dimensional motif along [100] formed by weak C—H···π interactions (shown as dashed lines).

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

Crystal data top

C₂₅H₂₃N₃O	F(000) = 808
M_r = 381.46	D_x = 1.220 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3374 reflections
a = 9.2694 (4) Å	θ = 3.5–29.0°
b = 18.3156 (8) Å	µ = 0.08 mm⁻¹
c = 12.6716 (7) Å	T = 293 K
β = 105.124 (5)°	Block, yellow
V = 2076.80 (17) Å³	0.30 × 0.30 × 0.20 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4077 independent reflections
Radiation source: fine-focus sealed tube	2343 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.5°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −22→19
T_min = 0.914, T_max = 1.000	l = −15→12
9542 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.132	w = 1/[σ²(F_o²) + (0.0435P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
4077 reflections	Δρ_max = 0.17 e Å⁻³
270 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0018 (5)

Crystal data top

C₂₅H₂₃N₃O	V = 2076.80 (17) Å³
M_r = 381.46	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.2694 (4) Å	µ = 0.08 mm⁻¹
b = 18.3156 (8) Å	T = 293 K
c = 12.6716 (7) Å	0.30 × 0.30 × 0.20 mm
β = 105.124 (5)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4077 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2343 reflections with I > 2σ(I)
T_min = 0.914, T_max = 1.000	R_int = 0.039
9542 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.17 e Å⁻³
4077 reflections	Δρ_min = −0.14 e Å⁻³
270 parameters

Special details top

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.37979 (16)	0.27791 (8)	0.08898 (14)	0.0507 (5)
N2	0.34012 (18)	0.35209 (9)	0.07998 (16)	0.0566 (5)
C3	0.1970 (2)	0.35428 (11)	0.03270 (17)	0.0497 (6)
C4	0.1351 (2)	0.28261 (10)	0.01024 (16)	0.0453 (5)
C5	0.2589 (2)	0.23347 (11)	0.04912 (16)	0.0466 (5)
O5	0.26105 (14)	0.16518 (7)	0.04952 (12)	0.0560 (4)
C6	0.1232 (2)	0.42734 (11)	0.0119 (2)	0.0711 (8)
H6A	0.1927	0.4645	0.0460	0.107*
H6B	0.0380	0.4284	0.0416	0.107*
H6C	0.0914	0.4361	−0.0654	0.107*
C7	0.5268 (2)	0.25907 (11)	0.14877 (18)	0.0489 (5)
C8	0.5900 (2)	0.19386 (12)	0.12908 (19)	0.0588 (6)
H8	0.5369	0.1621	0.0757	0.071*
C9	0.7325 (2)	0.17612 (13)	0.1892 (2)	0.0707 (7)
H9	0.7753	0.1322	0.1761	0.085*
C10	0.8117 (3)	0.22272 (15)	0.2681 (2)	0.0741 (8)
H10	0.9072	0.2102	0.3089	0.089*
C11	0.7492 (2)	0.28799 (14)	0.28674 (19)	0.0656 (7)
H11	0.8033	0.3198	0.3397	0.079*
C12	0.6064 (2)	0.30674 (12)	0.22733 (18)	0.0562 (6)
H12	0.5644	0.3509	0.2401	0.067*
C13	−0.0104 (2)	0.25866 (11)	−0.03560 (16)	0.0447 (5)
C14	−0.1359 (2)	0.31073 (10)	−0.07300 (16)	0.0426 (5)
C15	−0.2309 (2)	0.32528 (11)	−0.00777 (18)	0.0503 (6)
H15	−0.2187	0.3008	0.0583	0.060*
C16	−0.3446 (2)	0.37642 (12)	−0.04055 (19)	0.0574 (6)
H16	−0.4067	0.3861	0.0047	0.069*
C17	−0.3674 (2)	0.41302 (11)	−0.1384 (2)	0.0541 (6)
C18	−0.2724 (2)	0.39762 (12)	−0.20344 (18)	0.0593 (6)
H18	−0.2858	0.4217	−0.2699	0.071*
C19	−0.1579 (2)	0.34719 (11)	−0.17182 (17)	0.0555 (6)
H19	−0.0956	0.3377	−0.2170	0.067*
C20	−0.4894 (2)	0.46931 (12)	−0.1720 (2)	0.0826 (9)
H20A	−0.5745	0.4544	−0.1474	0.124*
H20B	−0.5176	0.4739	−0.2502	0.124*
H20C	−0.4538	0.5155	−0.1398	0.124*
N21	−0.0338 (2)	0.18632 (9)	−0.04121 (15)	0.0546 (5)
C22	−0.1653 (2)	0.14481 (11)	−0.08416 (18)	0.0503 (6)
C23	−0.1729 (3)	0.07733 (11)	−0.03820 (19)	0.0636 (7)
H23	−0.0940	0.0612	0.0186	0.076*
C24	−0.2965 (3)	0.03342 (13)	−0.0756 (2)	0.0750 (8)
H24	−0.2995	−0.0122	−0.0440	0.090*
C25	−0.4156 (3)	0.05601 (13)	−0.1591 (2)	0.0666 (7)
C26	−0.4042 (3)	0.12227 (13)	−0.2062 (2)	0.0676 (7)
H26	−0.4824	0.1379	−0.2639	0.081*
C27	−0.2809 (2)	0.16660 (12)	−0.17105 (19)	0.0621 (7)
H27	−0.2756	0.2109	−0.2057	0.074*
C28	−0.5540 (3)	0.00866 (15)	−0.1984 (3)	0.1072 (11)
H28A	−0.5999	0.0188	−0.2741	0.161*
H28B	−0.6235	0.0192	−0.1560	0.161*
H28C	−0.5261	−0.0419	−0.1900	0.161*
H21	0.060 (2)	0.1594 (11)	−0.0076 (17)	0.071 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0428 (9)	0.0367 (10)	0.0719 (12)	0.0019 (8)	0.0134 (8)	0.0041 (9)
N2	0.0461 (10)	0.0386 (10)	0.0830 (13)	0.0030 (8)	0.0129 (9)	0.0032 (9)
C3	0.0441 (11)	0.0432 (13)	0.0617 (14)	0.0017 (10)	0.0135 (10)	0.0022 (11)
C4	0.0409 (10)	0.0384 (12)	0.0571 (13)	0.0009 (9)	0.0136 (9)	0.0017 (10)
C5	0.0500 (12)	0.0393 (13)	0.0524 (13)	−0.0001 (10)	0.0167 (10)	0.0026 (11)
O5	0.0573 (9)	0.0382 (9)	0.0702 (10)	0.0036 (7)	0.0126 (8)	0.0043 (8)
C6	0.0557 (13)	0.0414 (13)	0.107 (2)	0.0041 (11)	0.0059 (13)	0.0020 (13)
C7	0.0434 (11)	0.0462 (13)	0.0589 (14)	0.0036 (10)	0.0165 (10)	0.0100 (11)
C8	0.0518 (13)	0.0508 (14)	0.0747 (16)	0.0046 (11)	0.0183 (11)	0.0078 (12)
C9	0.0602 (15)	0.0585 (16)	0.093 (2)	0.0177 (12)	0.0189 (14)	0.0180 (15)
C10	0.0546 (14)	0.0829 (19)	0.0786 (19)	0.0143 (14)	0.0063 (13)	0.0259 (16)
C11	0.0580 (14)	0.0756 (18)	0.0593 (15)	−0.0034 (13)	0.0084 (12)	0.0096 (13)
C12	0.0522 (12)	0.0586 (15)	0.0606 (14)	0.0035 (11)	0.0197 (11)	0.0062 (12)
C13	0.0487 (11)	0.0385 (12)	0.0502 (12)	0.0021 (10)	0.0187 (9)	0.0016 (10)
C14	0.0398 (10)	0.0402 (12)	0.0481 (12)	−0.0007 (9)	0.0119 (9)	−0.0011 (10)
C15	0.0489 (12)	0.0503 (14)	0.0540 (13)	−0.0028 (10)	0.0174 (10)	0.0030 (11)
C16	0.0471 (12)	0.0565 (14)	0.0725 (16)	−0.0016 (11)	0.0227 (11)	−0.0076 (13)
C17	0.0439 (12)	0.0397 (13)	0.0700 (16)	−0.0004 (10)	−0.0006 (11)	−0.0071 (12)
C18	0.0719 (15)	0.0464 (14)	0.0547 (14)	0.0044 (12)	0.0077 (12)	0.0075 (12)
C19	0.0662 (14)	0.0516 (14)	0.0529 (14)	0.0054 (11)	0.0228 (11)	0.0029 (11)
C20	0.0592 (15)	0.0561 (15)	0.116 (2)	0.0091 (12)	−0.0072 (15)	−0.0108 (15)
N21	0.0467 (10)	0.0416 (11)	0.0733 (13)	−0.0009 (9)	0.0117 (9)	0.0031 (10)
C22	0.0532 (12)	0.0380 (12)	0.0631 (14)	−0.0033 (10)	0.0211 (11)	−0.0037 (11)
C23	0.0741 (15)	0.0430 (14)	0.0709 (16)	−0.0051 (12)	0.0139 (13)	−0.0025 (12)
C24	0.1014 (19)	0.0424 (14)	0.0863 (18)	−0.0170 (14)	0.0338 (16)	−0.0045 (14)
C25	0.0684 (15)	0.0524 (15)	0.0857 (18)	−0.0165 (13)	0.0324 (14)	−0.0247 (14)
C26	0.0591 (14)	0.0579 (16)	0.0823 (17)	−0.0048 (12)	0.0120 (12)	−0.0122 (14)
C27	0.0601 (14)	0.0498 (14)	0.0724 (16)	−0.0072 (11)	0.0102 (12)	−0.0001 (12)
C28	0.099 (2)	0.089 (2)	0.140 (3)	−0.0458 (17)	0.0429 (19)	−0.038 (2)

Geometric parameters (Å, º) top

N1—C5	1.370 (2)	C15—H15	0.9300
N1—N2	1.404 (2)	C16—C17	1.377 (3)
N1—C7	1.418 (2)	C16—H16	0.9300
N2—C3	1.306 (2)	C17—C18	1.383 (3)
C3—C4	1.431 (3)	C17—C20	1.507 (3)
C3—C6	1.495 (3)	C18—C19	1.385 (3)
C4—C13	1.392 (2)	C18—H18	0.9300
C4—C5	1.440 (2)	C19—H19	0.9300
C5—O5	1.251 (2)	C20—H20A	0.9600
C6—H6A	0.9600	C20—H20B	0.9600
C6—H6B	0.9600	C20—H20C	0.9600
C6—H6C	0.9600	N21—C22	1.419 (2)
C7—C8	1.381 (3)	N21—H21	0.99 (2)
C7—C12	1.384 (3)	C22—C23	1.376 (3)
C8—C9	1.381 (3)	C22—C27	1.380 (3)
C8—H8	0.9300	C23—C24	1.378 (3)
C9—C10	1.372 (3)	C23—H23	0.9300
C9—H9	0.9300	C24—C25	1.378 (3)
C10—C11	1.375 (3)	C24—H24	0.9300
C10—H10	0.9300	C25—C26	1.369 (3)
C11—C12	1.384 (3)	C25—C28	1.521 (3)
C11—H11	0.9300	C26—C27	1.378 (3)
C12—H12	0.9300	C26—H26	0.9300
C13—N21	1.342 (2)	C27—H27	0.9300
C13—C14	1.483 (2)	C28—H28A	0.9600
C14—C15	1.382 (3)	C28—H28B	0.9600
C14—C19	1.386 (3)	C28—H28C	0.9600
C15—C16	1.390 (3)

C5—N1—N2	111.90 (14)	C17—C16—C15	121.6 (2)
C5—N1—C7	129.18 (16)	C17—C16—H16	119.2
N2—N1—C7	118.26 (15)	C15—C16—H16	119.2
C3—N2—N1	106.27 (15)	C16—C17—C18	117.72 (19)
N2—C3—C4	111.68 (17)	C16—C17—C20	121.0 (2)
N2—C3—C6	118.15 (18)	C18—C17—C20	121.2 (2)
C4—C3—C6	130.17 (17)	C17—C18—C19	121.5 (2)
C13—C4—C3	131.76 (18)	C17—C18—H18	119.2
C13—C4—C5	122.98 (18)	C19—C18—H18	119.2
C3—C4—C5	105.24 (15)	C18—C19—C14	120.2 (2)
O5—C5—N1	125.57 (16)	C18—C19—H19	119.9
O5—C5—C4	129.53 (17)	C14—C19—H19	119.9
N1—C5—C4	104.89 (16)	C17—C20—H20A	109.5
C3—C6—H6A	109.5	C17—C20—H20B	109.5
C3—C6—H6B	109.5	H20A—C20—H20B	109.5
H6A—C6—H6B	109.5	C17—C20—H20C	109.5
C3—C6—H6C	109.5	H20A—C20—H20C	109.5
H6A—C6—H6C	109.5	H20B—C20—H20C	109.5
H6B—C6—H6C	109.5	C13—N21—C22	131.33 (18)
C8—C7—C12	120.25 (18)	C13—N21—H21	110.9 (11)
C8—C7—N1	120.50 (19)	C22—N21—H21	117.8 (11)
C12—C7—N1	119.25 (18)	C23—C22—C27	118.87 (19)
C9—C8—C7	119.6 (2)	C23—C22—N21	116.91 (18)
C9—C8—H8	120.2	C27—C22—N21	124.16 (19)
C7—C8—H8	120.2	C22—C23—C24	120.5 (2)
C10—C9—C8	120.5 (2)	C22—C23—H23	119.7
C10—C9—H9	119.7	C24—C23—H23	119.7
C8—C9—H9	119.7	C25—C24—C23	121.1 (2)
C9—C10—C11	119.8 (2)	C25—C24—H24	119.5
C9—C10—H10	120.1	C23—C24—H24	119.5
C11—C10—H10	120.1	C26—C25—C24	117.6 (2)
C10—C11—C12	120.5 (2)	C26—C25—C28	121.1 (2)
C10—C11—H11	119.7	C24—C25—C28	121.2 (2)
C12—C11—H11	119.7	C25—C26—C27	122.2 (2)
C7—C12—C11	119.3 (2)	C25—C26—H26	118.9
C7—C12—H12	120.3	C27—C26—H26	118.9
C11—C12—H12	120.3	C26—C27—C22	119.6 (2)
N21—C13—C4	117.32 (17)	C26—C27—H27	120.2
N21—C13—C14	121.02 (17)	C22—C27—H27	120.2
C4—C13—C14	121.62 (17)	C25—C28—H28A	109.5
C15—C14—C19	118.75 (19)	C25—C28—H28B	109.5
C15—C14—C13	120.14 (18)	H28A—C28—H28B	109.5
C19—C14—C13	121.09 (19)	C25—C28—H28C	109.5
C14—C15—C16	120.2 (2)	H28A—C28—H28C	109.5
C14—C15—H15	119.9	H28B—C28—H28C	109.5
C16—C15—H15	119.9

C5—N1—N2—C3	−1.5 (2)	C3—C4—C13—C14	0.8 (3)
C7—N1—N2—C3	−173.05 (18)	C5—C4—C13—C14	178.85 (19)
N1—N2—C3—C4	1.1 (2)	N21—C13—C14—C15	77.8 (3)
N1—N2—C3—C6	−179.7 (2)	C4—C13—C14—C15	−99.8 (2)
N2—C3—C4—C13	178.0 (2)	N21—C13—C14—C19	−104.0 (2)
C6—C3—C4—C13	−1.1 (4)	C4—C13—C14—C19	78.3 (3)
N2—C3—C4—C5	−0.4 (2)	C19—C14—C15—C16	−1.0 (3)
C6—C3—C4—C5	−179.4 (2)	C13—C14—C15—C16	177.19 (17)
N2—N1—C5—O5	−178.0 (2)	C14—C15—C16—C17	0.9 (3)
C7—N1—C5—O5	−7.6 (4)	C15—C16—C17—C18	−0.4 (3)
N2—N1—C5—C4	1.2 (2)	C15—C16—C17—C20	−178.89 (18)
C7—N1—C5—C4	171.6 (2)	C16—C17—C18—C19	0.0 (3)
C13—C4—C5—O5	0.1 (4)	C20—C17—C18—C19	178.46 (18)
C3—C4—C5—O5	178.6 (2)	C17—C18—C19—C14	−0.1 (3)
C13—C4—C5—N1	−179.07 (19)	C15—C14—C19—C18	0.6 (3)
C3—C4—C5—N1	−0.5 (2)	C13—C14—C19—C18	−177.60 (18)
C5—N1—C7—C8	33.6 (3)	C4—C13—N21—C22	−178.6 (2)
N2—N1—C7—C8	−156.5 (2)	C14—C13—N21—C22	3.6 (4)
C5—N1—C7—C12	−146.3 (2)	C13—N21—C22—C23	−152.0 (2)
N2—N1—C7—C12	23.6 (3)	C13—N21—C22—C27	30.9 (4)
C12—C7—C8—C9	0.8 (3)	C27—C22—C23—C24	−2.4 (4)
N1—C7—C8—C9	−179.15 (19)	N21—C22—C23—C24	−179.6 (2)
C7—C8—C9—C10	0.0 (4)	C22—C23—C24—C25	−0.5 (4)
C8—C9—C10—C11	−0.7 (4)	C23—C24—C25—C26	2.5 (4)
C9—C10—C11—C12	0.7 (4)	C23—C24—C25—C28	−178.2 (2)
C8—C7—C12—C11	−0.7 (3)	C24—C25—C26—C27	−1.6 (4)
N1—C7—C12—C11	179.17 (19)	C28—C25—C26—C27	179.1 (2)
C10—C11—C12—C7	0.0 (3)	C25—C26—C27—C22	−1.3 (4)
C3—C4—C13—N21	−176.9 (2)	C23—C22—C27—C26	3.3 (4)
C5—C4—C13—N21	1.2 (3)	N21—C22—C27—C26	−179.7 (2)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C7–C12 ring

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···O5	0.99 (2)	1.82 (2)	2.702 (2)	146.4 (17)
C15—H15···Cgⁱ	0.93	2.63	3.470 (2)	152

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₃N₃O
M_r	381.46
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.2694 (4), 18.3156 (8), 12.6716 (7)
β (°)	105.124 (5)
V (Å³)	2076.80 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.914, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9542, 4077, 2343
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.132, 1.01
No. of reflections	4077
No. of parameters	270
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.14

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C7–C12 ring

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···O5	0.99 (2)	1.82 (2)	2.702 (2)	146.4 (17)
C15—H15···Cgⁱ	0.93	2.63	3.470 (2)	152

Symmetry code: (i) x−1, y, z.

Acknowledgements

RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003. VKG is thankful to the University of Jammu, Jammu, for financial support.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Ma, R.-M., Sun, S.-F. & Ng, S. W. (2006). Acta Cryst. E62, o4679–o4680. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, Y.-F., Li, J.-K., Wu, R.-T. & Zheng, Z.-B. (2007). Acta Cryst. E63, o2176–o2177. Web of Science CSD CrossRef IUCr Journals Google Scholar
Vyas, K. M., Jadeja, R. N., Gupta, V. K. & Surati, K. R. (2011). J. Mol. Struct. 990, 110–120. Web of Science CSD CrossRef CAS Google Scholar

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

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

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Experimental

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organic compounds

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