Ethyl 3-methyl-1-phenyl-5-(p-tol­yl)-1H-pyrazole-4-carboxyl­ate

Naveen, S.; Dileep Kumar, A.; Kumara, K.; Ajay Kumar, K.; Lokanath, N.K.; Warad, I.

doi:10.1107/S2414314616019726

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 12| December 2016| x161972

https://doi.org/10.1107/S2414314616019726

Open

access

Ethyl 3-methyl-1-phenyl-5-(p-tolyl)-1H-pyrazole-4-carboxylate

S. Naveen,^a A. Dileep Kumar,^b Karthik Kumara,^c K. Ajay Kumar,^b N. K. Lokanath ^c ^* and Ismail Warad ^d ^*

^aInstitution of Excellence, University of Mysore, Manasagangotri, Mysuru 570 006, India, ^bDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysuru 570 005, India, ^cDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysuru 570 006, India, and ^dDepartment of Chemistry, Science College, An-Najah National University, PO Box 7, Nablus, West Bank, Palestinian Territories
^*Correspondence e-mail: lokanath@physics.uni-mysore.ac.in, khalil.i@najah.edu

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 7 December 2016; accepted 9 December 2016; online 13 December 2016)

In the title compound, C₂₀H₂₀N₂O₂, the pyrazole ring makes dihedral angles of 39.74 (8) and 60.35 (8)° with the phenyl and toluene rings, respectively. The dihedral angle between the phenyl and toluene rings is 62.01 (7)°.

Keywords: crystal structure; pyrazole; C—H⋯π interactions.

CCDC reference: 1521904

Structure description

Pyrazoles are an important class of five-membered nitrogen heterocycles, which are very widely used as synthetic scaffolds for the construction of bioactive molecules (Ajay et al., 2015 ). Apart from their synthetic utilities, pyrazole derivatives themselves exhibit a broad spectrum of biological activities (Farghaly et al., 2012 ). As part of our studies in this area, we herein report on the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The pyrazole ring (N1/N2/C1–C3) makes dihedral angles of 39.74 (8) and 60.35 (8)° with the phenyl (C8–C13) and the toluene (C14–C19) rings, respectively. The dihedral angle between the phenyl and toluene rings is 62.01 (7)°.

Figure 1
The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

In the crystal, molecules are linked by C—H⋯π interactions, forming chains propagating along the a axis (Table 1 and Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1/N2/C1–C3 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯Cg1ⁱ	0.97	2.93	3.794 (2)	149
C19—H19⋯Cg2ⁱ	0.93	2.93	3.780 (2)	152
Symmetry code: (i) x-1, y, z.

Figure 2
A view along the a axis of the crystal packing of the title compound. The C—H⋯π interactions are shown as dashed lines (see Table 1

) and, for clarity, only H atoms H6A and H19 (grey balls) have been included.

Synthesis and crystallization

To a solution of (E)-ethyl 2-(4-methylbenzylidene)-3-oxobutanoate (0.01 mol), which was obtained by our earlier reported procedure (Naveen et al., 2016 ), and phenylhydrazine hydrochloride (0.01 mol) in ethyl alcohol (20 ml), 3–4 drops of piperidine were added. The mixture was refluxed on a water bath for 3 h. The progress of the reaction was monitored by TLC. After completion, the mixture was poured into ice-cold water and the solid separated was filtered, and washed with ice-cold water to obtain the crude title product. The solid obtained was crystallized from methanol by slow evaporation giving pale-yellow rectangular-shaped crystals (90% yield; m.p. 358–359 K).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₀H₂₀N₂O₂
M_r	320.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	6.2796 (3), 18.9391 (9), 14.6430 (7)
β (°)	91.406 (2)
V (Å³)	1740.97 (14)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.64
Crystal size (mm)	0.29 × 0.26 × 0.24

Data collection
Diffractometer	Bruker X8 Proteum
Absorption correction	Multi-scan (SADABS; Bruker, 2013 )
T_min, T_max	0.837, 0.863
No. of measured, independent and observed [I > 2σ(I)] reflections	13541, 2872, 2535
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.585

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.143, 1.06
No. of reflections	2872
No. of parameters	221
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.13
Computer programs: APEX2 and SAINT (Bruker, 2013), SHELXS97 and SHELXL97 (Sheldrick, 2008 ), Mercury (Macrae et al., 2008 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1521904

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314616019726/su4108sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616019726/su4108Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616019726/su4108Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Ethyl 3-methyl-1-phenyl-5-(p-tolyl)-1H-pyrazole-4-carboxylate top

Crystal data top

C₂₀H₂₀N₂O₂	F(000) = 680
M_r = 320.38	D_x = 1.222 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 2535 reflections
a = 6.2796 (3) Å	θ = 4.7–64.5°
b = 18.9391 (9) Å	µ = 0.64 mm⁻¹
c = 14.6430 (7) Å	T = 296 K
β = 91.406 (2)°	Block, yellow
V = 1740.97 (14) Å³	0.29 × 0.26 × 0.24 mm
Z = 4

Data collection top

Bruker X8 Proteum diffractometer	2872 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	2535 reflections with I > 2σ(I)
Helios multilayer optics monochromator	R_int = 0.042
Detector resolution: 18.4 pixels mm^-1	θ_max = 64.5°, θ_min = 4.7°
φ and ω scans	h = −6→7
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −21→22
T_min = 0.837, T_max = 0.863	l = −16→17
13541 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)] = 0.045	H-atom parameters constrained
wR(F²) = 0.143	w = 1/[σ²(F_o²) + (0.0929P)² + 0.1486P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2872 reflections	Δρ_max = 0.18 e Å⁻³
221 parameters	Δρ_min = −0.13 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: 0.0058 (12)

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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	−0.0474 (2)	0.37329 (6)	0.57248 (10)	0.0816 (5)
O2	−0.06959 (18)	0.48057 (6)	0.63324 (9)	0.0694 (4)
N1	0.48074 (19)	0.36844 (6)	0.76439 (8)	0.0500 (4)
N2	0.4568 (2)	0.43678 (6)	0.79382 (9)	0.0585 (4)
C1	0.3333 (2)	0.35112 (7)	0.69887 (9)	0.0457 (4)
C2	0.2068 (2)	0.41063 (7)	0.68588 (10)	0.0497 (5)
C3	0.2920 (2)	0.46213 (8)	0.74707 (11)	0.0558 (5)
C4	0.2198 (3)	0.53571 (9)	0.76614 (16)	0.0826 (7)
C5	0.0209 (2)	0.41723 (8)	0.62416 (11)	0.0537 (5)
C6	−0.2603 (3)	0.49523 (10)	0.57961 (14)	0.0736 (6)
C7	−0.3193 (4)	0.56968 (13)	0.5990 (2)	0.1036 (10)
C8	0.6407 (2)	0.32691 (7)	0.81037 (9)	0.0486 (4)
C9	0.8308 (2)	0.35962 (8)	0.83481 (10)	0.0551 (5)
C10	0.9844 (3)	0.32222 (9)	0.88330 (11)	0.0623 (5)
C11	0.9497 (3)	0.25341 (9)	0.90858 (11)	0.0660 (6)
C12	0.7601 (3)	0.22121 (9)	0.88390 (12)	0.0673 (6)
C13	0.6040 (3)	0.25754 (8)	0.83511 (11)	0.0600 (5)
C14	0.3253 (2)	0.28043 (7)	0.65589 (9)	0.0459 (4)
C15	0.4968 (2)	0.25452 (8)	0.60870 (10)	0.0559 (5)
C16	0.4894 (3)	0.18672 (9)	0.57228 (11)	0.0627 (6)
C17	0.3139 (3)	0.14384 (8)	0.58204 (10)	0.0586 (5)
C18	0.1417 (3)	0.17121 (8)	0.62768 (11)	0.0600 (5)
C19	0.1455 (2)	0.23851 (8)	0.66403 (10)	0.0523 (5)
C20	0.3068 (4)	0.06983 (9)	0.54428 (14)	0.0861 (8)
H4A	0.07700	0.53470	0.78810	0.1240*
H4B	0.22330	0.56310	0.71100	0.1240*
H4C	0.31270	0.55670	0.81160	0.1240*
H6A	−0.37410	0.46360	0.59660	0.0880*
H6B	−0.23410	0.48910	0.51510	0.0880*
H7A	−0.34320	0.57510	0.66310	0.1550*
H7B	−0.44700	0.58160	0.56500	0.1550*
H7C	−0.20590	0.60040	0.58130	0.1550*
H9	0.85470	0.40640	0.81870	0.0660*
H10	1.11310	0.34390	0.89910	0.0750*
H11	1.05320	0.22880	0.94210	0.0790*
H12	0.73690	0.17440	0.90030	0.0810*
H13	0.47590	0.23560	0.81910	0.0720*
H15	0.61700	0.28240	0.60130	0.0670*
H16	0.60540	0.16990	0.54060	0.0750*
H18	0.02060	0.14360	0.63400	0.0720*
H19	0.02750	0.25580	0.69400	0.0630*
H20A	0.35410	0.03720	0.59070	0.1290*
H20B	0.39830	0.06660	0.49290	0.1290*
H20C	0.16350	0.05850	0.52520	0.1290*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0878 (9)	0.0628 (8)	0.0926 (9)	0.0055 (6)	−0.0325 (7)	−0.0182 (6)
O2	0.0634 (7)	0.0566 (7)	0.0874 (8)	0.0107 (5)	−0.0141 (6)	−0.0085 (6)
N1	0.0539 (7)	0.0411 (6)	0.0547 (7)	−0.0030 (5)	−0.0019 (5)	−0.0072 (5)
N2	0.0651 (8)	0.0435 (7)	0.0665 (8)	−0.0021 (6)	−0.0072 (6)	−0.0127 (6)
C1	0.0480 (7)	0.0416 (7)	0.0476 (7)	−0.0049 (6)	0.0024 (6)	−0.0036 (6)
C2	0.0514 (8)	0.0425 (8)	0.0554 (8)	−0.0028 (6)	0.0036 (6)	−0.0040 (6)
C3	0.0599 (9)	0.0429 (8)	0.0646 (9)	−0.0014 (6)	0.0004 (7)	−0.0075 (7)
C4	0.0880 (13)	0.0513 (10)	0.1075 (15)	0.0084 (9)	−0.0172 (11)	−0.0246 (10)
C5	0.0553 (8)	0.0458 (8)	0.0602 (9)	−0.0034 (6)	0.0028 (7)	−0.0008 (7)
C6	0.0557 (9)	0.0732 (11)	0.0914 (13)	0.0050 (8)	−0.0087 (8)	0.0075 (9)
C7	0.0825 (14)	0.0865 (15)	0.141 (2)	0.0298 (12)	−0.0146 (14)	0.0011 (14)
C8	0.0544 (8)	0.0471 (8)	0.0443 (7)	−0.0018 (6)	0.0004 (6)	−0.0050 (6)
C9	0.0596 (9)	0.0526 (8)	0.0529 (8)	−0.0065 (7)	−0.0002 (7)	−0.0024 (6)
C10	0.0606 (9)	0.0696 (10)	0.0562 (9)	−0.0026 (7)	−0.0073 (7)	−0.0046 (7)
C11	0.0734 (11)	0.0681 (11)	0.0561 (9)	0.0117 (8)	−0.0079 (8)	−0.0008 (7)
C12	0.0848 (12)	0.0527 (9)	0.0642 (10)	0.0019 (8)	−0.0040 (8)	0.0054 (7)
C13	0.0653 (9)	0.0509 (9)	0.0635 (9)	−0.0079 (7)	−0.0024 (7)	−0.0001 (7)
C14	0.0527 (8)	0.0401 (7)	0.0447 (7)	−0.0015 (6)	−0.0015 (6)	−0.0028 (5)
C15	0.0555 (9)	0.0538 (9)	0.0586 (9)	−0.0014 (7)	0.0039 (7)	−0.0049 (7)
C16	0.0736 (10)	0.0595 (10)	0.0551 (9)	0.0184 (8)	0.0023 (7)	−0.0074 (7)
C17	0.0862 (11)	0.0392 (8)	0.0497 (8)	0.0059 (7)	−0.0135 (8)	−0.0011 (6)
C18	0.0748 (10)	0.0437 (8)	0.0610 (9)	−0.0127 (7)	−0.0065 (8)	0.0006 (7)
C19	0.0557 (8)	0.0460 (8)	0.0554 (8)	−0.0045 (6)	0.0028 (6)	−0.0041 (6)
C20	0.1353 (18)	0.0453 (9)	0.0765 (12)	0.0147 (10)	−0.0200 (12)	−0.0094 (8)

Geometric parameters (Å, º) top

O1—C5	1.197 (2)	C17—C18	1.386 (2)
O2—C5	1.3354 (19)	C17—C20	1.507 (2)
O2—C6	1.443 (2)	C18—C19	1.381 (2)
N1—N2	1.3736 (16)	C4—H4A	0.9600
N1—C1	1.3571 (17)	C4—H4B	0.9600
N1—C8	1.4310 (17)	C4—H4C	0.9600
N2—C3	1.3173 (19)	C6—H6A	0.9700
C1—C2	1.3893 (18)	C6—H6B	0.9700
C1—C14	1.4797 (19)	C7—H7A	0.9600
C2—C3	1.420 (2)	C7—H7B	0.9600
C2—C5	1.4640 (19)	C7—H7C	0.9600
C3—C4	1.494 (2)	C9—H9	0.9300
C6—C7	1.487 (3)	C10—H10	0.9300
C8—C9	1.3842 (18)	C11—H11	0.9300
C8—C13	1.384 (2)	C12—H12	0.9300
C9—C10	1.379 (2)	C13—H13	0.9300
C10—C11	1.374 (2)	C15—H15	0.9300
C11—C12	1.378 (3)	C16—H16	0.9300
C12—C13	1.382 (3)	C18—H18	0.9300
C14—C15	1.3837 (19)	C19—H19	0.9300
C14—C19	1.3878 (19)	C20—H20A	0.9600
C15—C16	1.391 (2)	C20—H20B	0.9600
C16—C17	1.379 (3)	C20—H20C	0.9600

C5—O2—C6	117.92 (13)	H4A—C4—H4B	109.00
N2—N1—C1	111.81 (11)	H4A—C4—H4C	109.00
N2—N1—C8	116.83 (11)	H4B—C4—H4C	109.00
C1—N1—C8	131.19 (11)	O2—C6—H6A	110.00
N1—N2—C3	105.73 (12)	O2—C6—H6B	110.00
N1—C1—C2	106.18 (12)	C7—C6—H6A	110.00
N1—C1—C14	122.33 (12)	C7—C6—H6B	110.00
C2—C1—C14	131.49 (12)	H6A—C6—H6B	109.00
C1—C2—C3	105.40 (12)	C6—C7—H7A	110.00
C1—C2—C5	126.75 (13)	C6—C7—H7B	109.00
C3—C2—C5	127.82 (12)	C6—C7—H7C	109.00
N2—C3—C2	110.89 (13)	H7A—C7—H7B	109.00
N2—C3—C4	118.75 (14)	H7A—C7—H7C	110.00
C2—C3—C4	130.33 (14)	H7B—C7—H7C	109.00
O1—C5—O2	122.73 (14)	C8—C9—H9	120.00
O1—C5—C2	126.78 (14)	C10—C9—H9	120.00
O2—C5—C2	110.49 (13)	C9—C10—H10	120.00
O2—C6—C7	106.61 (17)	C11—C10—H10	120.00
N1—C8—C9	117.82 (12)	C10—C11—H11	120.00
N1—C8—C13	121.71 (13)	C12—C11—H11	120.00
C9—C8—C13	120.36 (13)	C11—C12—H12	120.00
C8—C9—C10	119.41 (14)	C13—C12—H12	120.00
C9—C10—C11	120.82 (16)	C8—C13—H13	120.00
C10—C11—C12	119.40 (16)	C12—C13—H13	120.00
C11—C12—C13	120.83 (16)	C14—C15—H15	120.00
C8—C13—C12	119.17 (16)	C16—C15—H15	120.00
C1—C14—C15	120.97 (12)	C15—C16—H16	119.00
C1—C14—C19	120.02 (12)	C17—C16—H16	119.00
C15—C14—C19	119.00 (13)	C17—C18—H18	119.00
C14—C15—C16	119.99 (13)	C19—C18—H18	119.00
C15—C16—C17	121.55 (16)	C14—C19—H19	120.00
C16—C17—C18	117.69 (15)	C18—C19—H19	120.00
C16—C17—C20	121.75 (17)	C17—C20—H20A	109.00
C18—C17—C20	120.56 (17)	C17—C20—H20B	110.00
C17—C18—C19	121.65 (15)	C17—C20—H20C	109.00
C14—C19—C18	120.08 (13)	H20A—C20—H20B	109.00
C3—C4—H4A	110.00	H20A—C20—H20C	109.00
C3—C4—H4B	109.00	H20B—C20—H20C	109.00
C3—C4—H4C	109.00

C6—O2—C5—O1	1.5 (2)	C5—C2—C3—N2	178.10 (14)
C6—O2—C5—C2	−177.83 (13)	C5—C2—C3—C4	0.1 (3)
C5—O2—C6—C7	−176.98 (16)	C1—C2—C5—O1	−3.0 (3)
C1—N1—N2—C3	0.62 (16)	C1—C2—C5—O2	176.28 (13)
C8—N1—N2—C3	−175.18 (12)	C3—C2—C5—O1	179.34 (16)
N2—N1—C1—C2	−0.61 (15)	C3—C2—C5—O2	−1.4 (2)
N2—N1—C1—C14	179.93 (12)	N1—C8—C9—C10	176.73 (13)
C8—N1—C1—C2	174.41 (13)	C13—C8—C9—C10	0.7 (2)
C8—N1—C1—C14	−5.1 (2)	N1—C8—C13—C12	−176.41 (14)
N2—N1—C8—C9	−39.04 (17)	C9—C8—C13—C12	−0.5 (2)
N2—N1—C8—C13	136.99 (14)	C8—C9—C10—C11	−0.9 (2)
C1—N1—C8—C9	146.15 (14)	C9—C10—C11—C12	1.0 (3)
C1—N1—C8—C13	−37.8 (2)	C10—C11—C12—C13	−0.8 (3)
N1—N2—C3—C2	−0.38 (16)	C11—C12—C13—C8	0.6 (3)
N1—N2—C3—C4	177.88 (14)	C1—C14—C15—C16	177.18 (13)
N1—C1—C2—C3	0.35 (15)	C19—C14—C15—C16	−1.6 (2)
N1—C1—C2—C5	−177.75 (13)	C1—C14—C19—C18	−176.92 (13)
C14—C1—C2—C3	179.74 (14)	C15—C14—C19—C18	1.9 (2)
C14—C1—C2—C5	1.6 (2)	C14—C15—C16—C17	−0.1 (2)
N1—C1—C14—C15	−60.00 (19)	C15—C16—C17—C18	1.6 (2)
N1—C1—C14—C19	118.79 (15)	C15—C16—C17—C20	−178.80 (16)
C2—C1—C14—C15	120.70 (17)	C16—C17—C18—C19	−1.3 (2)
C2—C1—C14—C19	−60.5 (2)	C20—C17—C18—C19	179.07 (16)
C1—C2—C3—N2	0.03 (16)	C17—C18—C19—C14	−0.4 (2)
C1—C2—C3—C4	−177.97 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N1/N2/C1–C3 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···Cg1ⁱ	0.97	2.93	3.794 (2)	149
C19—H19···Cg2ⁱ	0.93	2.93	3.780 (2)	152

Symmetry code: (i) x−1, y, z.

Acknowledgements

The authors are grateful to the Institution of Excellence, Vijnana Bhavana, University of Mysore, India, for providing the single-crystal X-ray diffractometer facility.

References

Ajay Kumar, K. & Govindaraju, M. (2015). Int. J. ChemTech Res. 8, 313–322. Google Scholar
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farghaly, A.-R., Esmail, S., Ali, A.-H., Vanelle, P. & El-Kashef, H. (2012). Arkivoc. vii. 228–241. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Naveen, S., Dileep Kumar, A., Ajay Kumar, K. & Lokanath, N. K. (2016). Chem. Data Coll. 3–4, 1–7. 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 12| December 2016| x161972

https://doi.org/10.1107/S2414314616019726

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Ethyl 3-methyl-1-phenyl-5-(p-tol­yl)-1H-pyrazole-4-carboxyl­ate

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

Ethyl 3-methyl-1-phenyl-5-(p-tolyl)-1H-pyrazole-4-carboxylate