2-[(5-Amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)(4-chloro­phen­yl)meth­yl]malononitrile

Zhang, X.-Y.; Li, X.-Y.; Wang, X.; Li, D.-F.; Fan, X.-S.

doi:10.1107/S1600536808011562

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o908

doi:10.1107/S1600536808011562

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2-[(5-Amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)(4-chlorophenyl)methyl]malononitrile

Xin-Ying Zhang,^a ^* Xiao-Yan Li,^a Xia Wang,^a Dong-Fang Li ^a and Xue-Sen Fan ^a ^*

^aSchool of Chemical and Environmental Sciences, Henan Key Laboratory for Environmental Pollution Control, Henan Normal University, Xinxiang, Henan 453007, People's Republic of China
^*Correspondence e-mail: xyzh518@sohu.com, xuesen.fan@sohu.com

(Received 17 April 2008; accepted 22 April 2008; online 26 April 2008)

In the crystal structure of the title compound, C₂₀H₁₆ClN₅, the dihedral angle between the pyrazole ring and the phenyl ring is 54.7 (1)° and that between the pyrazole ring and the chloro-substituted phenyl ring is 72.4 (1)°. The methyl H atoms are disordered over two positions with site occupancy factors of ca 0.7 and 0.3. One amino H is disordered equally over two positions. In the crystal structure, the molecules are linked via intermolecular N—H⋯N hydrogen bonding.

Experimental

Crystal data

C₂₀H₁₆ClN₅
M_r = 361.83
Orthorhombic, P b c a
a = 10.4700 (11) Å
b = 14.0482 (15) Å
c = 25.409 (3) Å
V = 3737.3 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 294 (2) K
0.49 × 0.48 × 0.45 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.901, T_max = 0.908
32456 measured reflections
4661 independent reflections
3055 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.118
S = 1.03
4661 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯N4ⁱ	0.86	2.41	3.159 (2)	146
N3—H2N3⋯N2ⁱⁱ	0.86	2.53	3.325 (2)	155
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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: 10.1107/S1600536808011562/nc2101sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808011562/nc2101Isup2.hkl

checkCIF report

Comment top

The structure determination was undertaken as a part of a project on the synthesis of new pyrazole derivatives. In the title compound the dihedral angle between the pyrazole ring and the non-substituted phenyl ring which is directly connected to the pyrazole ring is 54.7 (1)° and that between the pyrazole ring and the chloro-substituted phenyl ring is 72.4 (1)°. The dihedral angle between the non-substituted and the chloro-substituted phenyl ring amount to 69.7 (1)° (Fig. 1).

In the crystal structure the molecules are connected via intermolecular N—H···N hydrogen bonding between the amino group at N3 and the N atoms N2 and N4 (Fig. 2 and Table 1).

Experimental top

To 1 ml of 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim][BF₄]), 4-chloroaldehyde (1 mmol), malononitrile (1 mmol) and 5-amino-3-methyl-1-phenylpyrazole (1 mmol) were added. The reaction mixture was stirred at room temperature for 4 h and afterwards extracted five times with 2 ml of diethylether. The ether extracts were combined and concentrated. The obtained residue was recrystallized with 95% ethanol to give the product in a yield of 95% as white solid. Single crystals of the title compound were obtained by slow evaporation of the solvent from a petroleum ether-ethyl ether (1:1 v/v) solution.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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. Molecular structure of the title compound, with labelling displacement ellipsoids drawn at the 30% probability level. The disordering of the H atoms is not shown for clarity.
	Fig. 2. Crystal structure of the title compound with view along the a-axis. Intermolecular N—H···N hydrogen bonding is shown as dashed lines and the disordering of the H atoms is not shown for clarity.

2-[(5-Amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)(4- chlorophenyl)methyl]malononitrile top

Crystal data top

C₂₀H₁₆ClN₅	D_x = 1.286 Mg m⁻³
M_r = 361.83	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 8329 reflections
a = 10.4700 (11) Å	θ = 2.5–25.8°
b = 14.0482 (15) Å	µ = 0.22 mm⁻¹
c = 25.409 (3) Å	T = 294 K
V = 3737.3 (7) Å³	Block, colourless
Z = 8	0.49 × 0.48 × 0.45 mm
F(000) = 1504

Data collection top

Bruker SMART CCD area-detector diffractometer	4661 independent reflections
Radiation source: fine-focus sealed tube	3055 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 28.4°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −14→13
T_min = 0.901, T_max = 0.909	k = −18→18
32456 measured reflections	l = −33→33

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)] = 0.041	H-atom parameters constrained
wR(F²) = 0.118	w = 1/[σ²(F_o²) + (0.0404P)² + 1.3457P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
4661 reflections	Δρ_max = 0.18 e Å⁻³
237 parameters	Δρ_min = −0.32 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: 0.0012 (3)

Crystal data top

C₂₀H₁₆ClN₅	V = 3737.3 (7) Å³
M_r = 361.83	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 10.4700 (11) Å	µ = 0.22 mm⁻¹
b = 14.0482 (15) Å	T = 294 K
c = 25.409 (3) Å	0.49 × 0.48 × 0.45 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4661 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	3055 reflections with I > 2σ(I)
T_min = 0.901, T_max = 0.909	R_int = 0.033
32456 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.03	Δρ_max = 0.18 e Å⁻³
4661 reflections	Δρ_min = −0.32 e Å⁻³
237 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	Occ. (<1)
Cl1	0.34596 (7)	1.04230 (4)	0.53076 (2)	0.0837 (2)
N1	0.27144 (14)	0.71251 (10)	0.78626 (5)	0.0509 (4)
N2	0.17726 (15)	0.64522 (12)	0.77803 (6)	0.0605 (4)
N3	0.43568 (16)	0.79533 (11)	0.74011 (5)	0.0623 (4)
N4	0.4155 (2)	0.44105 (12)	0.68772 (7)	0.0751 (5)
N5	0.52582 (19)	0.58634 (13)	0.54493 (7)	0.0748 (5)
C1	0.18531 (16)	0.62494 (13)	0.72710 (6)	0.0512 (4)
C2	0.28333 (15)	0.67629 (11)	0.70228 (5)	0.0414 (3)
C3	0.33723 (15)	0.73171 (11)	0.74145 (6)	0.0429 (4)
C4	0.0940 (2)	0.55545 (17)	0.70288 (8)	0.0772 (7)
H4A	0.0613	0.5811	0.6706	0.116*	0.73
H4B	0.0245	0.5440	0.7267	0.116*	0.73
H4C	0.1376	0.4967	0.6958	0.116*	0.73
H4D	0.0876	0.5001	0.7249	0.116*	0.27
H4E	0.1244	0.5372	0.6687	0.116*	0.27
H4F	0.0114	0.5845	0.6996	0.116*	0.27
C5	0.29537 (17)	0.74496 (15)	0.83845 (6)	0.0579 (5)
C6	0.2963 (2)	0.84064 (18)	0.84956 (9)	0.0847 (7)
H6	0.2812	0.8854	0.8233	0.102*
C7	0.3206 (3)	0.8691 (3)	0.90156 (14)	0.1220 (14)
H7	0.3232	0.9335	0.9099	0.146*
C8	0.3407 (3)	0.8023 (4)	0.94005 (12)	0.1401 (18)
H8	0.3567	0.8218	0.9744	0.168*
C9	0.3375 (3)	0.7080 (3)	0.92837 (10)	0.1239 (13)
H9	0.3504	0.6632	0.9548	0.149*
C10	0.3151 (2)	0.6782 (2)	0.87746 (8)	0.0846 (7)
H10	0.3133	0.6136	0.8695	0.102*
C11	0.33508 (15)	0.76013 (11)	0.61584 (5)	0.0415 (3)
C12	0.22572 (17)	0.79784 (13)	0.59298 (6)	0.0516 (4)
H12	0.1491	0.7647	0.5956	0.062*
C13	0.2283 (2)	0.88387 (14)	0.56630 (6)	0.0588 (5)
H13	0.1545	0.9082	0.5510	0.071*
C14	0.3417 (2)	0.93244 (12)	0.56298 (6)	0.0550 (5)
C15	0.45228 (19)	0.89664 (13)	0.58425 (7)	0.0569 (5)
H15	0.5287	0.9299	0.5811	0.068*
C16	0.44836 (17)	0.81010 (12)	0.61058 (6)	0.0510 (4)
H16	0.5230	0.7853	0.6249	0.061*
C17	0.32395 (14)	0.66623 (11)	0.64546 (5)	0.0401 (3)
H17	0.2568	0.6296	0.6278	0.048*
C18	0.44800 (16)	0.60557 (11)	0.64192 (6)	0.0444 (4)
H18	0.5153	0.6391	0.6613	0.053*
C19	0.42937 (18)	0.51193 (13)	0.66700 (6)	0.0525 (4)
C20	0.49158 (17)	0.59315 (12)	0.58707 (7)	0.0511 (4)
H1N3	0.4639	0.8173	0.7695	0.061*
H2N3	0.5027	0.7693	0.7270	0.061*	0.50
H3N3	0.4647	0.8134	0.7101	0.061*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1235 (5)	0.0600 (3)	0.0677 (3)	0.0238 (3)	0.0273 (3)	0.0234 (2)
N1	0.0586 (9)	0.0588 (8)	0.0354 (7)	−0.0138 (7)	0.0064 (6)	−0.0075 (6)
N2	0.0636 (9)	0.0760 (11)	0.0418 (8)	−0.0252 (8)	0.0098 (7)	−0.0067 (7)
N3	0.0761 (11)	0.0659 (9)	0.0448 (8)	−0.0308 (8)	0.0096 (7)	−0.0120 (7)
N4	0.1013 (14)	0.0569 (10)	0.0669 (11)	0.0076 (9)	−0.0131 (10)	0.0121 (8)
N5	0.0918 (13)	0.0807 (12)	0.0518 (9)	0.0059 (10)	0.0158 (9)	−0.0074 (8)
C1	0.0543 (10)	0.0587 (10)	0.0405 (8)	−0.0137 (8)	0.0015 (7)	−0.0033 (7)
C2	0.0474 (8)	0.0430 (8)	0.0338 (7)	−0.0020 (7)	0.0003 (6)	−0.0009 (6)
C3	0.0505 (9)	0.0416 (8)	0.0365 (7)	−0.0045 (7)	0.0040 (6)	−0.0021 (6)
C4	0.0765 (14)	0.0976 (16)	0.0575 (11)	−0.0416 (12)	0.0044 (10)	−0.0101 (11)
C5	0.0542 (10)	0.0810 (13)	0.0384 (8)	−0.0124 (9)	0.0110 (7)	−0.0155 (8)
C6	0.0862 (16)	0.0897 (16)	0.0782 (14)	−0.0306 (13)	0.0300 (12)	−0.0365 (12)
C7	0.102 (2)	0.157 (3)	0.107 (2)	−0.063 (2)	0.0500 (18)	−0.088 (2)
C8	0.091 (2)	0.268 (5)	0.0613 (17)	−0.046 (3)	0.0176 (15)	−0.071 (3)
C9	0.112 (2)	0.220 (4)	0.0398 (12)	0.002 (3)	0.0031 (13)	−0.0061 (18)
C10	0.0911 (17)	0.120 (2)	0.0427 (10)	0.0025 (15)	0.0073 (10)	−0.0001 (12)
C11	0.0507 (9)	0.0458 (8)	0.0281 (7)	0.0033 (7)	0.0007 (6)	−0.0010 (6)
C12	0.0513 (10)	0.0586 (10)	0.0449 (9)	0.0051 (8)	−0.0033 (7)	0.0022 (7)
C13	0.0670 (12)	0.0632 (11)	0.0461 (9)	0.0200 (10)	−0.0025 (8)	0.0052 (8)
C14	0.0803 (13)	0.0494 (9)	0.0353 (8)	0.0139 (9)	0.0115 (8)	0.0056 (7)
C15	0.0649 (11)	0.0555 (10)	0.0503 (10)	−0.0040 (9)	0.0091 (8)	0.0076 (8)
C16	0.0514 (10)	0.0555 (10)	0.0462 (9)	0.0005 (8)	−0.0012 (7)	0.0083 (7)
C17	0.0450 (8)	0.0438 (8)	0.0315 (7)	−0.0024 (7)	−0.0039 (6)	−0.0020 (6)
C18	0.0516 (9)	0.0471 (9)	0.0345 (7)	0.0018 (7)	−0.0056 (6)	−0.0022 (6)
C19	0.0623 (11)	0.0530 (10)	0.0421 (8)	0.0088 (8)	−0.0079 (8)	−0.0005 (7)
C20	0.0560 (10)	0.0515 (10)	0.0457 (9)	0.0062 (8)	0.0001 (8)	−0.0027 (7)

Geometric parameters (Å, º) top

Cl1—C14	1.7477 (17)	C6—H6	0.9300
N1—C3	1.3577 (19)	C7—C8	1.371 (5)
N1—N2	1.3819 (19)	C7—H7	0.9300
N1—C5	1.424 (2)	C8—C9	1.359 (5)
N2—C1	1.328 (2)	C8—H8	0.9300
N3—C3	1.365 (2)	C9—C10	1.379 (3)
N3—H1N3	0.8602	C9—H9	0.9300
N3—H2N3	0.8587	C10—H10	0.9300
N3—H3N3	0.8595	C11—C16	1.385 (2)
N4—C19	1.136 (2)	C11—C12	1.389 (2)
N5—C20	1.133 (2)	C11—C17	1.523 (2)
C1—C2	1.404 (2)	C12—C13	1.386 (2)
C1—C4	1.499 (2)	C12—H12	0.9300
C2—C3	1.384 (2)	C13—C14	1.372 (3)
C2—C17	1.5117 (19)	C13—H13	0.9300
C4—H4A	0.9600	C14—C15	1.373 (3)
C4—H4B	0.9600	C15—C16	1.388 (2)
C4—H4C	0.9600	C15—H15	0.9300
C4—H4D	0.9600	C16—H16	0.9300
C4—H4E	0.9600	C17—C18	1.556 (2)
C4—H4F	0.9600	C17—H17	0.9800
C5—C6	1.373 (3)	C18—C19	1.475 (2)
C5—C10	1.380 (3)	C18—C20	1.477 (2)
C6—C7	1.404 (4)	C18—H18	0.9800

C3—N1—N2	111.78 (12)	C7—C6—H6	120.9
C3—N1—C5	128.89 (14)	C8—C7—C6	120.3 (3)
N2—N1—C5	119.03 (13)	C8—C7—H7	119.8
C1—N2—N1	104.41 (13)	C6—C7—H7	119.8
C3—N3—H1N3	118.2	C9—C8—C7	120.5 (3)
C3—N3—H2N3	110.3	C9—C8—H8	119.8
H1N3—N3—H2N3	102.1	C7—C8—H8	119.8
C3—N3—H3N3	118.9	C8—C9—C10	120.3 (3)
H1N3—N3—H3N3	122.9	C8—C9—H9	119.8
H2N3—N3—H3N3	59.4	C10—C9—H9	119.8
N2—C1—C2	111.96 (14)	C9—C10—C5	119.6 (3)
N2—C1—C4	119.96 (16)	C9—C10—H10	120.2
C2—C1—C4	128.07 (15)	C5—C10—H10	120.2
C3—C2—C1	105.31 (13)	C16—C11—C12	118.19 (15)
C3—C2—C17	128.66 (14)	C16—C11—C17	123.53 (14)
C1—C2—C17	125.92 (14)	C12—C11—C17	118.29 (14)
N1—C3—N3	122.28 (14)	C13—C12—C11	121.41 (17)
N1—C3—C2	106.52 (13)	C13—C12—H12	119.3
N3—C3—C2	131.19 (14)	C11—C12—H12	119.3
C1—C4—H4A	109.5	C14—C13—C12	118.72 (17)
C1—C4—H4B	109.5	C14—C13—H13	120.6
H4A—C4—H4B	109.5	C12—C13—H13	120.6
C1—C4—H4C	109.5	C13—C14—C15	121.56 (16)
H4A—C4—H4C	109.5	C13—C14—Cl1	119.35 (15)
H4B—C4—H4C	109.5	C15—C14—Cl1	119.09 (16)
C1—C4—H4D	109.5	C14—C15—C16	119.04 (18)
H4A—C4—H4D	141.1	C14—C15—H15	120.5
H4B—C4—H4D	56.3	C16—C15—H15	120.5
H4C—C4—H4D	56.3	C11—C16—C15	121.05 (16)
C1—C4—H4E	109.5	C11—C16—H16	119.5
H4A—C4—H4E	56.3	C15—C16—H16	119.5
H4B—C4—H4E	141.1	C2—C17—C11	114.36 (12)
H4C—C4—H4E	56.3	C2—C17—C18	109.95 (12)
H4D—C4—H4E	109.5	C11—C17—C18	112.45 (12)
C1—C4—H4F	109.5	C2—C17—H17	106.5
H4A—C4—H4F	56.3	C11—C17—H17	106.5
H4B—C4—H4F	56.3	C18—C17—H17	106.5
H4C—C4—H4F	141.1	C19—C18—C20	110.08 (14)
H4D—C4—H4F	109.5	C19—C18—C17	110.68 (14)
H4E—C4—H4F	109.5	C20—C18—C17	112.15 (13)
C6—C5—C10	121.1 (2)	C19—C18—H18	107.9
C6—C5—N1	120.4 (2)	C20—C18—H18	107.9
C10—C5—N1	118.53 (19)	C17—C18—H18	107.9
C5—C6—C7	118.2 (3)	N4—C19—C18	177.99 (18)
C5—C6—H6	120.9	N5—C20—C18	178.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···N4ⁱ	0.86	2.41	3.159 (2)	146
N3—H2N3···N2ⁱⁱ	0.86	2.53	3.325 (2)	155

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆ClN₅
M_r	361.83
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	294
a, b, c (Å)	10.4700 (11), 14.0482 (15), 25.409 (3)
V (Å³)	3737.3 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.49 × 0.48 × 0.45

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.901, 0.909
No. of measured, independent and observed [I > 2σ(I)] reflections	32456, 4661, 3055
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.118, 1.03
No. of reflections	4661
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.32

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), 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
N3—H1N3···N4ⁱ	0.86	2.41	3.159 (2)	146.2
N3—H2N3···N2ⁱⁱ	0.86	2.53	3.325 (2)	154.6

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 20772025), the Program for Science & Technology Innovation Talents in Universities of Henan Province (No. 2008HASTIT006) and the Department of Education of Henan Province (No. 2008 A150013).

References

Bruker (1997). SMART and SAINT. 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

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Volume 64| Part 5| May 2008| Page o908

doi:10.1107/S1600536808011562

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

2-[(5-Amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)(4-chloro­phen­yl)meth­yl]malono­nitrile

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-[(5-Amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)(4-chlorophenyl)methyl]malononitrile