5-Methyl-4-(3-methyl-1-phenyl-1H-pyrazol-4-yl)-2-phenyl-2,3-di­hydro-1H-pyrazol-3-one

Ghandour, I.; Mague, J.T.; Bouayad, A.; Chakroune, S.; Essassi, E.M.; Kandri Rodi, Y.

doi:10.1107/S2414314617008537

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 6| June 2017| x170853

https://doi.org/10.1107/S2414314617008537

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5-Methyl-4-(3-methyl-1-phenyl-1H-pyrazol-4-yl)-2-phenyl-2,3-dihydro-1H-pyrazol-3-one

Ismail Ghandour,^a Joel T. Mague,^b Abdelouahed Bouayad,^a ^* Said Chakroune,^c El Mokhtar Essassi ^d and Youssef Kandri Rodi ^c

^aLaboratoire de Chimie de la Matière Condensée, Université Sidi Mohamed Ben Abdellah, Facultédes Sciences et Techniques, Route d'Immouzzer, BP 2202, Fez, Morocco, ^bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^cLaboratory of Applied Organic Chemistry, Faculty of Science and Technology, University Sidi Mohammed Ben Abdellah, Fez, Morocco, and ^dLaboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco
^*Correspondence e-mail: abdelouahedbouayad07@gmail.com

Edited by J. Simpson, University of Otago, New Zealand (Received 29 May 2017; accepted 8 June 2017; online 13 June 2017)

In the title compound, C₂₀H₁₈N₄O, the dihedral angle between the pyrazole and pyrazolone rings is 69.35 (3)° and an intramolecular C—H⋯O hydrogen bond encloses an R₂²(6) ring. In the crystal, the packing features N—H⋯O and C—H⋯O hydrogen bonds and C—H⋯π(ring) interactions.

Keywords: crystal structure; pyrazolone; pyrazole; hydrogen bonds.

CCDC reference: 1554813

Structure description

Materials containing pyrazolone ring systems represent an important class of compounds, not only for their theoretical interest, but also because of their pharmaceutical applications. These include use as anti-inflammatory, analgesic, antipyretic (El-Sayed & El-Ashmawey, 1998 ) and hypoglycemic agents (Das et al., 2008 ). They also have fungicidal (Singh & Singh, 1991 ) and antimicrobial properties (Sahu et al., 2007 ) and some have been tested as potential cardiovascular drugs (Higashi et al., 2006 ). In the past year, research has focused on existing molecules and their modifications in order to reduce side effects and to explore other pharmacological and biological effects. As part of our work in this area, the synthesis and structure of the title compound, Fig. 1, are described here.

Figure 1
The title molecule with the labeling scheme and 50% probability ellipsoids.

An intramolecular C6—H6⋯O1 hydrogen bond encloses an R₂²(6) ring and affects the conformation of the phenylpyrazalone segment of the molecule. The dihedral angle between the C1–C6 phenyl ring and the N1/N2/C7–C9 pyrazolone ring is 16.56 (6)° while that between the pyrazolone and pyrazole rings is 69.35 (3)°. The corresponding dihedral angle between the C15–C20 phenyl ring and the N3/N4/C11–C13 pyrazole ring is 39.72 (5)°.

In the crystal the strongest intermolecular interaction is the N2—H2A⋯O1ⁱ hydrogen bond (Table 1, Figs. 2 and 3. This is supported by a C2—H2⋯O1ⁱ hydrogen bond and together they link molecules into chains along the c-axis direction. The packing is further facilitated by four C—H⋯π(ring) interactions, as illustrated in Fig. 3.

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg3 and Cg4 are the centroids of the N3/N4/C11–C13, C1–C6 and C15–C20 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.948 (17)	1.788 (17)	2.7326 (12)	173.8 (15)
C2—H2⋯O1ⁱ	0.991 (16)	2.490 (16)	3.2058 (15)	128.8 (12)
C6—H6⋯O1	0.976 (16)	2.282 (16)	2.9210 (15)	122.2 (12)
C5—H5⋯Cg3ⁱⁱ	0.997 (17)	2.706 (16)	3.6201 (15)	153.0 (12)
C10—H10A⋯Cg2ⁱⁱⁱ	0.94 (2)	2.79 (2)	3.5373 (13)	136.5 (18)
C10—H10B⋯Cg4^iv	0.98 (2)	2.83 (2)	3.7117 (14)	150.3 (17)
C14—H14B⋯Cg2^v	0.99 (2)	2.77 (2)	3.6861 (16)	154.9 (16)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (v) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 2
Packing viewed along the b axis with intermolecular N—H⋯O hydrogen bonds shown as dotted lines.

Figure 3
Details of the C—H⋯π(ring) interactions (purple dotted lines) and the N—H⋯O hydrogen bond (blue dotted line) [symmetry codes: (i) x, $[{1\over 2}]$ − y, $[{1\over 2}]$ + z; (ii) 1 − x, − $[{1\over 2}]$ + y, $[{3\over 2}]$ − z; (iii) −x, − $[{1\over 2}]$ + y, $[{3\over 2}]$ − z; (iv) x, $[{3\over 2}]$ − y, $[{1\over 2}]$ + z].

Synthesis and crystallization

To a solution of dehydroacetic acid (0.168 g, 1 mmol), copper(II) sulfate pentahydrate (0.249 g, 1 mmol) was added as a catalyst together with a solution of phenylhydrazine (0.099 ml, 1 mmol) in absolute ethanol (30 ml). The reaction mixture was stirred for 3 h at 351 K. Colorless block-like crystals were obtained after cooling the reaction to 298 K (yield = 67%; m.p. = 523 K).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₀H₁₈N₄O
M_r	330.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	18.2838 (13), 7.7956 (6), 11.8081 (8)
β (°)	100.393 (3)
V (Å³)	1655.4 (2)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.68
Crystal size (mm)	0.22 × 0.18 × 0.10

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.86, 0.94
No. of measured, independent and observed [I > 2σ(I)] reflections	12696, 3308, 3049
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.093, 1.05
No. of reflections	3308
No. of parameters	299
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.18
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1554813

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617008537/sj4116sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S2414314617008537/sj4116Isup2.cdx

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617008537/sj4116Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617008537/sj4116Isup4.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

5-Methyl-4-(3-methyl-1-phenyl-1H-pyrazol-4-yl)-2-phenyl-2,3-dihydro-1H-pyrazol-3-one top

Crystal data top

C₂₀H₁₈N₄O	F(000) = 696
M_r = 330.38	D_x = 1.326 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 18.2838 (13) Å	Cell parameters from 9980 reflections
b = 7.7956 (6) Å	θ = 2.5–74.7°
c = 11.8081 (8) Å	µ = 0.68 mm⁻¹
β = 100.393 (3)°	T = 150 K
V = 1655.4 (2) Å³	Block, colourless
Z = 4	0.22 × 0.18 × 0.10 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3308 independent reflections
Radiation source: INCOATEC IµS micro-focus source	3049 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.029
Detector resolution: 10.4167 pixels mm^-1	θ_max = 74.7°, θ_min = 4.9°
ω scans	h = −22→21
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −9→8
T_min = 0.86, T_max = 0.94	l = −14→14
12696 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	All H-atom parameters refined
wR(F²) = 0.093	w = 1/[σ²(F_o²) + (0.0463P)² + 0.5397P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3308 reflections	Δρ_max = 0.22 e Å⁻³
299 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0106 (7)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.21528 (5)	0.21776 (12)	0.67688 (6)	0.0285 (2)
N1	0.19857 (5)	0.27643 (12)	0.86378 (7)	0.0197 (2)
N2	0.24072 (5)	0.35100 (12)	0.96039 (7)	0.0201 (2)
H2A	0.2330 (9)	0.319 (2)	1.0348 (14)	0.038 (4)*
N3	0.43012 (5)	0.45260 (12)	0.61521 (8)	0.0230 (2)
N4	0.36552 (5)	0.46088 (12)	0.65819 (8)	0.0200 (2)
C1	0.12381 (6)	0.22855 (14)	0.86357 (9)	0.0205 (2)
C2	0.08809 (7)	0.28638 (17)	0.95115 (10)	0.0284 (3)
H2	0.1155 (9)	0.361 (2)	1.0123 (14)	0.037 (4)*
C3	0.01570 (7)	0.2340 (2)	0.95303 (12)	0.0366 (3)
H3	−0.0102 (10)	0.275 (2)	1.0193 (16)	0.053 (5)*
C4	−0.02153 (7)	0.12675 (19)	0.86882 (12)	0.0368 (3)
H4	−0.0718 (10)	0.086 (2)	0.8707 (15)	0.046 (4)*
C5	0.01404 (7)	0.07181 (18)	0.78120 (12)	0.0339 (3)
H5	−0.0117 (9)	−0.007 (2)	0.7206 (14)	0.045 (4)*
C6	0.08652 (7)	0.12168 (16)	0.77770 (10)	0.0279 (3)
H6	0.1116 (9)	0.084 (2)	0.7157 (13)	0.034 (4)*
C7	0.23913 (6)	0.27631 (14)	0.77497 (9)	0.0203 (2)
C8	0.30915 (6)	0.35407 (13)	0.82245 (9)	0.0193 (2)
C9	0.30790 (6)	0.39215 (13)	0.93601 (9)	0.0194 (2)
C10	0.36562 (7)	0.46954 (16)	1.02632 (10)	0.0260 (3)
H10A	0.3676 (12)	0.418 (3)	1.099 (2)	0.080 (7)*
H10B	0.3533 (12)	0.589 (3)	1.0386 (18)	0.072 (6)*
H10C	0.4149 (13)	0.468 (3)	1.0048 (19)	0.073 (6)*
C11	0.37120 (6)	0.37597 (14)	0.76121 (9)	0.0196 (2)
C12	0.44289 (6)	0.31276 (15)	0.78571 (10)	0.0229 (2)
H12	0.4657 (9)	0.2424 (19)	0.8532 (13)	0.033 (4)*
C13	0.47676 (6)	0.36365 (15)	0.69282 (10)	0.0234 (2)
C14	0.55367 (7)	0.32664 (19)	0.67266 (12)	0.0324 (3)
H14A	0.5929 (12)	0.389 (3)	0.7326 (19)	0.071 (6)*
H14B	0.5649 (12)	0.203 (3)	0.6810 (18)	0.072 (6)*
H14C	0.5598 (10)	0.364 (2)	0.5934 (15)	0.046 (5)*
C15	0.30487 (6)	0.55447 (13)	0.59520 (9)	0.0202 (2)
C16	0.29122 (7)	0.54406 (14)	0.47580 (9)	0.0237 (2)
H16	0.3224 (8)	0.4722 (18)	0.4379 (12)	0.028 (4)*
C17	0.23177 (7)	0.63393 (16)	0.41357 (10)	0.0291 (3)
H17	0.2205 (8)	0.622 (2)	0.3278 (14)	0.035 (4)*
C18	0.18726 (7)	0.73638 (16)	0.46884 (12)	0.0322 (3)
H18	0.1438 (10)	0.800 (2)	0.4241 (15)	0.045 (4)*
C19	0.20264 (7)	0.74963 (17)	0.58769 (12)	0.0316 (3)
H19	0.1711 (9)	0.821 (2)	0.6277 (14)	0.045 (4)*
C20	0.26126 (7)	0.65856 (15)	0.65170 (10)	0.0253 (3)
H20	0.2732 (8)	0.6686 (19)	0.7353 (13)	0.031 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0274 (4)	0.0447 (5)	0.0145 (4)	−0.0073 (4)	0.0070 (3)	−0.0068 (3)
N1	0.0204 (5)	0.0261 (5)	0.0134 (4)	−0.0009 (3)	0.0052 (3)	−0.0016 (3)
N2	0.0233 (5)	0.0250 (5)	0.0127 (4)	−0.0012 (4)	0.0050 (4)	−0.0012 (3)
N3	0.0205 (5)	0.0274 (5)	0.0239 (5)	−0.0001 (4)	0.0111 (4)	0.0004 (4)
N4	0.0203 (5)	0.0234 (5)	0.0184 (4)	0.0008 (3)	0.0087 (4)	0.0019 (3)
C1	0.0193 (5)	0.0243 (5)	0.0189 (5)	0.0019 (4)	0.0058 (4)	0.0043 (4)
C2	0.0238 (6)	0.0416 (7)	0.0211 (5)	0.0027 (5)	0.0078 (5)	0.0000 (5)
C3	0.0257 (6)	0.0572 (9)	0.0302 (6)	0.0025 (6)	0.0136 (5)	0.0023 (6)
C4	0.0228 (6)	0.0478 (8)	0.0416 (7)	−0.0027 (5)	0.0109 (5)	0.0065 (6)
C5	0.0261 (6)	0.0376 (7)	0.0380 (7)	−0.0055 (5)	0.0058 (5)	−0.0031 (6)
C6	0.0252 (6)	0.0320 (6)	0.0277 (6)	−0.0014 (5)	0.0080 (5)	−0.0036 (5)
C7	0.0226 (5)	0.0247 (5)	0.0150 (5)	0.0010 (4)	0.0069 (4)	0.0009 (4)
C8	0.0218 (5)	0.0214 (5)	0.0158 (5)	−0.0001 (4)	0.0063 (4)	0.0015 (4)
C9	0.0225 (5)	0.0192 (5)	0.0171 (5)	0.0008 (4)	0.0051 (4)	0.0019 (4)
C10	0.0291 (6)	0.0291 (6)	0.0193 (5)	−0.0039 (5)	0.0033 (5)	−0.0025 (4)
C11	0.0226 (5)	0.0211 (5)	0.0160 (5)	−0.0011 (4)	0.0060 (4)	0.0000 (4)
C12	0.0229 (6)	0.0250 (6)	0.0210 (5)	0.0011 (4)	0.0048 (4)	0.0008 (4)
C13	0.0215 (5)	0.0247 (6)	0.0252 (5)	0.0000 (4)	0.0073 (4)	−0.0018 (4)
C14	0.0231 (6)	0.0401 (7)	0.0365 (7)	0.0047 (5)	0.0117 (5)	0.0007 (6)
C15	0.0207 (5)	0.0202 (5)	0.0204 (5)	−0.0025 (4)	0.0056 (4)	0.0022 (4)
C16	0.0282 (6)	0.0228 (5)	0.0209 (5)	−0.0051 (4)	0.0071 (5)	0.0005 (4)
C17	0.0336 (7)	0.0282 (6)	0.0236 (6)	−0.0082 (5)	0.0000 (5)	0.0055 (5)
C18	0.0277 (6)	0.0300 (6)	0.0367 (7)	−0.0001 (5)	−0.0004 (5)	0.0090 (5)
C19	0.0287 (6)	0.0302 (6)	0.0368 (7)	0.0056 (5)	0.0086 (5)	0.0034 (5)
C20	0.0266 (6)	0.0268 (6)	0.0239 (6)	0.0031 (4)	0.0079 (5)	0.0013 (4)

Geometric parameters (Å, º) top

O1—C7	1.2482 (13)	C8—C11	1.4611 (14)
N1—N2	1.3842 (12)	C9—C10	1.4862 (16)
N1—C7	1.3894 (13)	C10—H10A	0.94 (2)
N1—C1	1.4165 (14)	C10—H10B	0.98 (2)
N2—C9	1.3498 (14)	C10—H10C	0.98 (2)
N2—H2A	0.948 (17)	C11—C12	1.3813 (16)
N3—C13	1.3289 (15)	C12—C13	1.4102 (15)
N3—N4	1.3686 (12)	C12—H12	0.995 (16)
N4—C11	1.3723 (13)	C13—C14	1.4961 (16)
N4—C15	1.4204 (14)	C14—H14A	1.03 (2)
C1—C6	1.3920 (17)	C14—H14B	0.99 (2)
C1—C2	1.3939 (15)	C14—H14C	1.006 (18)
C2—C3	1.3890 (18)	C15—C16	1.3892 (15)
C2—H2	0.991 (16)	C15—C20	1.3897 (15)
C3—C4	1.381 (2)	C16—C17	1.3871 (17)
C3—H3	1.036 (19)	C16—H16	0.965 (15)
C4—C5	1.386 (2)	C17—C18	1.3848 (19)
C4—H4	0.977 (18)	C17—H17	1.000 (16)
C5—C6	1.3887 (17)	C18—C19	1.3845 (19)
C5—H5	0.997 (17)	C18—H18	1.001 (17)
C6—H6	0.976 (16)	C19—C20	1.3899 (18)
C7—C8	1.4359 (15)	C19—H19	0.983 (18)
C8—C9	1.3777 (14)	C20—H20	0.975 (15)

N2—N1—C7	109.19 (9)	C9—C10—H10B	110.0 (13)
N2—N1—C1	120.38 (8)	H10A—C10—H10B	104.2 (18)
C7—N1—C1	130.15 (9)	C9—C10—H10C	112.2 (13)
C9—N2—N1	108.47 (8)	H10A—C10—H10C	110.2 (18)
C9—N2—H2A	123.6 (10)	H10B—C10—H10C	107.3 (18)
N1—N2—H2A	120.0 (10)	N4—C11—C12	105.95 (9)
C13—N3—N4	104.96 (9)	N4—C11—C8	123.62 (10)
N3—N4—C11	111.94 (9)	C12—C11—C8	130.31 (10)
N3—N4—C15	118.33 (8)	C11—C12—C13	105.67 (10)
C11—N4—C15	129.72 (9)	C11—C12—H12	127.6 (9)
C6—C1—C2	120.03 (11)	C13—C12—H12	126.7 (9)
C6—C1—N1	120.32 (10)	N3—C13—C12	111.47 (10)
C2—C1—N1	119.64 (10)	N3—C13—C14	119.70 (10)
C3—C2—C1	119.49 (12)	C12—C13—C14	128.81 (11)
C3—C2—H2	121.3 (9)	C13—C14—H14A	110.9 (12)
C1—C2—H2	119.2 (9)	C13—C14—H14B	110.9 (13)
C4—C3—C2	120.90 (12)	H14A—C14—H14B	106.5 (17)
C4—C3—H3	120.0 (10)	C13—C14—H14C	110.9 (10)
C2—C3—H3	119.1 (10)	H14A—C14—H14C	108.7 (15)
C3—C4—C5	119.22 (12)	H14B—C14—H14C	108.8 (15)
C3—C4—H4	121.7 (10)	C16—C15—C20	120.51 (11)
C5—C4—H4	119.1 (10)	C16—C15—N4	118.80 (10)
C4—C5—C6	120.97 (13)	C20—C15—N4	120.66 (10)
C4—C5—H5	120.3 (10)	C17—C16—C15	119.23 (11)
C6—C5—H5	118.7 (10)	C17—C16—H16	121.3 (8)
C5—C6—C1	119.38 (11)	C15—C16—H16	119.4 (8)
C5—C6—H6	121.2 (9)	C18—C17—C16	120.84 (11)
C1—C6—H6	119.4 (9)	C18—C17—H17	120.0 (9)
O1—C7—N1	123.78 (10)	C16—C17—H17	119.2 (9)
O1—C7—C8	130.87 (10)	C19—C18—C17	119.44 (12)
N1—C7—C8	105.35 (9)	C19—C18—H18	119.7 (10)
C9—C8—C7	107.50 (9)	C17—C18—H18	120.9 (10)
C9—C8—C11	127.39 (10)	C18—C19—C20	120.58 (12)
C7—C8—C11	124.98 (9)	C18—C19—H19	120.0 (10)
N2—C9—C8	109.39 (9)	C20—C19—H19	119.4 (10)
N2—C9—C10	119.95 (9)	C15—C20—C19	119.35 (11)
C8—C9—C10	130.65 (10)	C15—C20—H20	119.3 (9)
C9—C10—H10A	112.6 (14)	C19—C20—H20	121.3 (9)

C7—N1—N2—C9	−2.24 (12)	C7—C8—C9—C10	178.44 (11)
C1—N1—N2—C9	−176.77 (9)	C11—C8—C9—C10	2.4 (2)
C13—N3—N4—C11	−0.78 (12)	N3—N4—C11—C12	0.82 (12)
C13—N3—N4—C15	177.91 (9)	C15—N4—C11—C12	−177.69 (10)
N2—N1—C1—C6	−166.17 (10)	N3—N4—C11—C8	−175.64 (10)
C7—N1—C1—C6	20.60 (18)	C15—N4—C11—C8	5.86 (17)
N2—N1—C1—C2	12.62 (15)	C9—C8—C11—N4	−128.38 (12)
C7—N1—C1—C2	−160.61 (11)	C7—C8—C11—N4	56.22 (16)
C6—C1—C2—C3	1.15 (19)	C9—C8—C11—C12	56.09 (18)
N1—C1—C2—C3	−177.64 (11)	C7—C8—C11—C12	−119.31 (14)
C1—C2—C3—C4	−0.5 (2)	N4—C11—C12—C13	−0.51 (12)
C2—C3—C4—C5	−0.3 (2)	C8—C11—C12—C13	175.62 (11)
C3—C4—C5—C6	0.6 (2)	N4—N3—C13—C12	0.43 (13)
C4—C5—C6—C1	0.0 (2)	N4—N3—C13—C14	178.99 (10)
C2—C1—C6—C5	−0.85 (18)	C11—C12—C13—N3	0.05 (13)
N1—C1—C6—C5	177.93 (11)	C11—C12—C13—C14	−178.34 (12)
N2—N1—C7—O1	−179.69 (10)	N3—N4—C15—C16	39.09 (14)
C1—N1—C7—O1	−5.87 (19)	C11—N4—C15—C16	−142.49 (11)
N2—N1—C7—C8	0.41 (12)	N3—N4—C15—C20	−139.05 (11)
C1—N1—C7—C8	174.23 (10)	C11—N4—C15—C20	39.37 (16)
O1—C7—C8—C9	−178.38 (12)	C20—C15—C16—C17	−2.36 (16)
N1—C7—C8—C9	1.52 (12)	N4—C15—C16—C17	179.50 (10)
O1—C7—C8—C11	−2.21 (19)	C15—C16—C17—C18	1.51 (17)
N1—C7—C8—C11	177.68 (10)	C16—C17—C18—C19	0.29 (18)
N1—N2—C9—C8	3.23 (12)	C17—C18—C19—C20	−1.27 (19)
N1—N2—C9—C10	−177.99 (9)	C16—C15—C20—C19	1.40 (17)
C7—C8—C9—N2	−2.95 (12)	N4—C15—C20—C19	179.50 (11)
C11—C8—C9—N2	−179.00 (10)	C18—C19—C20—C15	0.44 (19)

Hydrogen-bond geometry (Å, º) top

Cg2, Cg3 and Cg4 are the centroids of the N3/N4/C11–C13, C1–C6 and C15–C20 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.948 (17)	1.788 (17)	2.7326 (12)	173.8 (15)
C2—H2···O1ⁱ	0.991 (16)	2.490 (16)	3.2058 (15)	128.8 (12)
C6—H6···O1	0.976 (16)	2.282 (16)	2.9210 (15)	122.2 (12)
C5—H5···Cg3ⁱⁱ	0.997 (17)	2.706 (16)	3.6201 (15)	153.0 (12)
C10—H10A···Cg2ⁱⁱⁱ	0.94 (2)	2.79 (2)	3.5373 (13)	136.5 (18)
C10—H10B···Cg4^iv	0.98 (2)	2.83 (2)	3.7117 (14)	150.3 (17)
C14—H14B···Cg2^v	0.99 (2)	2.77 (2)	3.6861 (16)	154.9 (16)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x, y−1/2, −z+3/2; (iii) x, −y−1/2, z−1/2; (iv) x, −y+1/2, z−1/2; (v) −x+1, y−1/2, −z+3/2.

Acknowledgements

The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 2| Part 6| June 2017| x170853

https://doi.org/10.1107/S2414314617008537

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

5-Methyl-4-(3-methyl-1-phenyl-1H-pyrazol-4-yl)-2-phenyl-2,3-di­hydro-1H-pyrazol-3-one

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

5-Methyl-4-(3-methyl-1-phenyl-1H-pyrazol-4-yl)-2-phenyl-2,3-dihydro-1H-pyrazol-3-one