Crystal structure of 6-amino-3-methyl-4-phenyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile European Journal of Chemistry 15 (2) (2024) 143-148 European Journal of Chemistry ISSN 2153-2249 (Print) / ISSN 2153-2257 (Online) – Copyright © 2024 The Authors – Atlanta Publishing House LLC – Printed in the USA. This work is published and licensed by Atlanta Publishing House LLC – CC BY NC – Some Rights Reserved. https://dx.doi.org/10.5155/eurjchem.15.2.143-148.2525 European Journal of Chemistry View Journal Online View Article Online Crystal structure of 6-amino-3-methyl-4-phenyl-2,4-dihydropyrano [2,3-c]pyrazole-5-carbonitrile Naresh Sharma 1,*, Indrajit Karmakar 2, Goutam Brahmachari 2 and Vivek Kumar Gupta 3 1 Department of Physics, Government Degree College Billawar, Billawar-184204, (J&K) India 2 Laboratory of Natural Products and Organic Synthesis, Department of Chemistry, Visva-Bharati (A Central University), Santiniketan-731235, West Bengal, India 3 Department of Physics, University of Jammu, Jammu Tawi-180006, India * Corresponding author at: Department of Physics, Government Degree College Billawar, Billawar-184204, (J&K) India. e-mail: nareshbasotra@gmail.com (N. Sharma). 10.5155/eurjchem.15.2.143-148.2525 Received: 22 February 2024 Received in revised form: 8 April 2024 Accepted: 27 April 2024 Published online: 30 June 2024 Printed: 30 June 2024 The crystal structure of the title compound, 6-amino-3-methyl-4-phenyl-2,4- dihydropyrano[2,3-c]pyrazole-5-carbonitrile, were determined by single crystal X-ray structure analysis. The compound C14H12N4O crystallizes in the triclinic crystal system with the P-1 space group (no. 2), having unit cell parameters a = 6.4788(7) Å, b = 8.8433(7) Å, c = 10.7377(9) Å, α = 103.456(7)°, β = 99.207(8)°, γ = 92.451(8)°, V = 588.55(9) Å3, Z = 2. The crystal structure was solved by direct methods using single-crystal X-ray diffraction data collected at room temperature and refined by full-matrix least-squares procedure with a final R-value of 0.0464 for 1432 observed reflections. The dihedral angle between the pyran ring and the pyrazole ring is 178.08(6)°, between the pyrazole ring and the benzene ring is 98.92(6)° and between the pyran ring and the benzene ring is 97.10(5)°. The molecules in the crystal are linked to an infinite two-dimensional network by N−H···N and C−H···π types of hydrogen bonds. Molecules are also reinforced by the π···π interaction between the pyrazole ring and the pyran ring, respectively. Carbonitrile Direct methods Dihydropyrano Hydrogen bonding Biological properties X-ray crystallography Cite this: Eur. J. Chem. 2024, 15(2), 143-148 Journal website: www.eurjchem.com 1. Introduction Pyrano[2,3-c]pyrazole is a heterocyclic compound that has garnered significant attention in the field of organic chemistry due to its unique structural characteristics and a diverse range of potential applications. This fused-ring system consists of a pyrazole ring fused to a pyran ring, resulting in a complex yet intriguing molecular framework. The synthesis and charac- terization of pyrano[2,3-c]pyrazole derivatives have been the subject of extensive research efforts, driven by the promising biological activities of the compound and its potential pharma- cological properties. The synthesis of pyrano[2,3-c]pyrazole derivatives has been the subject of intense investigation, with researchers exploring innovative synthetic methodologies to access structurally diverse compounds with enhanced biolo- gical properties. The development of efficient synthetic routes and strategies for the preparation of pyrano[2,3-c]pyrazole derivatives has been crucial in expanding the chemical space and exploring the structure-activity relationships of these compounds. Pyrano[2,3-c] pyrazole scaffolds represent a 'privileged' structural motif, well distributed in bioactive natural products and pharmaceutically potent synthetic heterocycles that possess a wide range of activities such as antiviral [1], insecticidal [2], molluscicidal [3], antimicrobial [4], analgesic [5], hypotensive [6], hypoglycemic and anticancer agents [7-9]. Pyrano[2,3-c]pyrazole framework present in natural and synthetic organic compounds is reported to be responsible for imparting potent biological properties, anti- inflammatory [10,11], antimicrobial [12-14], anti-angiogenesis [15], Chk1 inhibitor activity [16], and analgesic [17], and molluscicidal activity [18]. The present communication aims to disclose the crystal structure of a member of this series of bio- logically important scaffolds, 6-amino-3-methyl-4-phenyl-2, 4- dihydropyrano[2,3-c]pyrazole-5-carbo-nitrile [19,20]. This research publication aims to provide a comprehensive over- view of the synthesis, structural characterization, and biological evaluation of pyrano[2,3-c]pyrazole derivatives. By highlight- ing the synthetic strategies employed, the structural modifica- tions made, and the pharmacological potential exhibited by the pyrano[2,3-c]pyrazole derivatives, this study contributes to the growing body of knowledge on heterocyclic chemistry and drug discovery. Exploring of pyrano[2,3-c]pyrazole derivatives as potential drug candidates holds great promise for the develop- ment of novel therapeutic agents with improved efficacy and reduced side effects, thus addressing unmet medical needs and advancing the field of medicinal chemistry. ABSTRACT RESEARCH ARTICLE KEYWORDS https://dx.doi.org/10.5155/eurjchem.15.2.143-148.2525 https://www.eurjchem.com/ https://dx.doi.org/10.5155/eurjchem.15.2.143-148.2525 mailto:nareshbasotra@gmail.com http://www.eurjchem.com/ https://crossmark.crossref.org/dialog/?doi=10.5155/eurjchem.15.2.143-148.2525&domain=pdf&date_stamp=2024-06-30 144 Sharma et al. / European Journal of Chemistry 15 (2) (2024) 143-148 2024 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.15.2.143-148.2525 Table 1. Crystallographic characteristics, details of X-ray data collection, and structure refinement parameters for the title compound. Empirical formula C14H12N4O Formula weight (g/mol) 252.28 Temperature (K) 293(2) Crystal system Triclinic Space group P-1 a, (Å) 6.4788(7) b, (Å) 8.8433(7) c, (Å) 10.7377(9) α (°) 103.456(7) β (°) 99.207(8) γ (°) 92.451(8) Volume (Å3) 588.55(9) Z 2 ρcalc (g/cm3) 1.424 μ (mm-1) 0.095 F(000) 264.0 Crystal size (mm3) 0.3 × 0.2 × 0.2 Radiation MoKα (λ = 0.71073) 2Θ range for data collection (°) 6.88 to 49.98 Index ranges -4 ≤ h ≤ 7, -10 ≤ k ≤ 10, -12 ≤ l ≤ 12 Reflections collected 3695 Independent reflections 2073 [Rint = 0.0304, Rsigma = 0.0645] Data/restraints/parameters 2073/0/185 Goodness-of-fit on F2 0.996 Final R indexes [I≥2σ (I)] R1 = 0.0464, wR2 = 0.0966 Final R indexes [all data] R1 = 0.0768, wR2 = 0.1104 Largest diff. peak/hole (e.Å-3) 0.21/-0.22 Scheme 1. Synthesis of 6-amino-3-methyl-4-phenyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile, 5. 2. Experimental 2.1. Synthesis of 6-amino-3-methyl-4-phenyl-2,4-dihydro pyrano[2,3-c]pyrazole-5-carbonitrile (5) An oven-dried screw-cap test tube was sequentially charged with a magnetic stirrer bar, ethyl acetoacetate (1, 1 mmol) and hydrazine hydrate (2, 1 mmol) (Scheme 1). The reaction mixture was vigorously stirred at room temperature for about 10 minutes to generate the corresponding pyrazole derivative 3 in situ. The resulting reaction mixture was then added with malononitrile (3, 1.1 mmol), benzaldehyde (4, 1 mmol), trisodium citrate dihydrate (10 mol%), and EtOH/H2O (1:1, v/v, 4 mL), followed by vigorous stirring at room temperature for another 2 h. The progress of the reaction was monitored by TLC. At the end of the reaction, a solid mass was precipitated, which was filtered off and washed with aqueous ethanol to obtain the crude product 6-amino-3-methyl-4- phenyl-2, 4-dihydropyrano[2, 3-c]pyrazole-5-carbonitrile, 5. The product was purified (with 76% yield) by recrystallization from ethanol, upon which we obtained single crystals. 2.2. Synthesis of single crystal A single crystal was obtained using dimethyl sulfoxide (DMSO) as a solvent. For crystallization, 50 mg of the compound, 6-amino-3-methyl-4-phenyl-2, 4-dihydropyrano [2, 3-c]pyrazole-5-carbonitrile (molecular formula C14H12N4O) was dissolved in 5 ml of DMSO and left for several days at room temperature, which produced block-shaped crystals suitable for XRD analysis. 2.3. Crystal structure determination and refinement X-ray intensity data of 3695 reflections (of which 2073 unique) were collected on X’calibur CCD area-detector diffract- tometer equipped with graphite monochromated MoKα radiation (λ = 0.71073 Å). The crystal used for data collection was of dimensions 0.30×0.20×0.20 mm. The cell dimensions were determined by least-squares fit of angular settings of 1276 reflections in the θ range 3.81 to 28.61°. The intensities were measured by ω scan mode for θ ranges 3.44 to 24.99°. 2073 reflections were treated as observed (I > 2σ(I)). Data were corrected for Lorentz, polarization, and absorption factors. The structure was solved by direct methods using SHELXS97 [21]. The positions of the amino and H2 attached to the N2 atoms were determined from a difference Fourier map and refined isotropically. All remaining H atoms were geometrically fixed and allowed to ride on their parent C atoms with C-H = 0.93- 0.98 Å, and Uiso(H) = 1.5 Ueq(C) of the attached C atoms for the methyl H atoms and 1.2 Ueq for the other H atoms. Full-matrix least squares refinement was carried out using SHELXL97 [21]. The final refinement cycles converged to an R = 0.0464 and wR(F2) = 0.1104 for the observed data. Residual electron densities ranged from -0.220 to 0.209 e.Å-3. The crystallo- graphic data for the title compound are summarized in Table 1. 3. Results and discussion The crystal structure consists of a three-ring system, the pyran ring, the pyrazole ring, and the benzene ring (Figure 1). The benzene ring and the pyrazole ring are nearly planar with a maximum deviation of 0.0027 Å for the benzene C13 atom and 0.0038 Å for the pyrazole C7A atom. Sharma et al. / European Journal of Chemistry 15 (2) (2024) 143-148 145 2024 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.15.2.143-148.2525 Table 2. Bond lengths for the title compound. Atom Atom Length (Å) Atom Atom Length (Å) N1 N2 1.364(2) C6 O7 1.377(2) N1 C7A 1.320(3) C6 N17 1.348(3) N2 C3 1.355(3) O7 C7A 1.374(2) C3 C3A 1.380(3) C8 C9 1.384(3) C3 C14 1.488(3) C8 C13 1.382(3) C3A C4 1.500(3) C9 C10 1.387(3) C3A C7A 1.382(3) C10 C11 1.377(3) C4 C5 1.526(3) C11 C12 1.372(3) C4 C8 1.526(3) C12 C13 1.386(3) C5 C6 1.354(3) C15 N16 1.149(3) C5 C15 1.415(3) Table 3. Bond angles for the title compound. Atom Atom Atom Angle (°) Atom Atom Atom Angle (°) C7A N1 N2 101.42(17) N17 C6 C5 127.4(2) C3 N2 N1 113.87(18) N17 C6 O7 108.99(19) N2 C3 C3A 105.66(18) C7A O7 C6 114.57(17) N2 C3 C14 122.21(19) N1 C7A C3A 115.17(18) C3A C3 C14 132.1(2) N1 C7A O7 118.77(18) C3 C3A C4 132.80(19) O7 C7A C3A 126.05(19) C3 C3A C7A 103.87(18) C9 C8 C4 120.3(2) C7A C3A C4 123.33(18) C13 C8 C4 121.55(19) C3A C4 C5 106.05(16) C13 C8 C9 118.09(19) C3A C4 C8 112.18(15) C8 C9 C10 120.9(2) C8 C4 C5 112.05(16) C11 C10 C9 120.2(2) C6 C5 C4 126.15(18) C12 C11 C10 119.5(2) C6 C5 C15 116.96(18) C11 C12 C13 120.1(2) C15 C5 C4 116.88(18) C8 C13 C12 121.2(2) C5 C6 O7 123.62(18) N16 C15 C5 178.9(2) Figure 1. The molecular structure of the title compound, displacement ellipsoids were drawn at 40% probability level. Furthermore, in the molecule, the pyran ring is essentially planar and deviates slightly from the planarity with a maximum torsion angle equal to 5.2(3)° for C3A/C4/C5/C6. The pyran and pyrazole rings are fused through the common atoms C7a and C3a. In the molecule, the expected geometric parameters are observed. The overall molecular geometry of the title compound, including bond distances [22], has a normal range and corresponds to those observed in related structures [23- 26]. The six C-C bond lengths in the benzene ring range from 1.372(4) to 1.387(4) Å with an average value of 1.381(4) Å (Table 2). The bond angles in this benzene ring vary from 118.1(2) to 121.2(3)° with an average value of 120(3)°, which coincides exactly with the theoretical value of sp2-hybridization (Table 3). The dihedral angle between the pyran ring and the pyrazole ring is 178.08(6)°, between the pyrazole ring and the benzene ring is 98.92(6)° and between the pyran ring and the benzene ring is 97.10(5)° (Table 4). From the dihedral angle between the pyrazole ring and pyran ring, it shows that these rings are nearly coplanar to each other. The torsion angle C15-C5-C6-O7 = 176.31(18)° and N17-C6-O7-C7A = 179.87(17)° conveys that the carbon atom C15 and the nitrogen atom of the amino group lie almost in the plane of the pyran ring. In addition, the torsion angle C14-C3-C3A-C4 = 0.5(4)° shows that the C14 atom of the methyl group lies in the plane of the pyrazole ring. The exocyclic bond angles at the ring junction, that is, at C3A and C7A, are 132.8(2) and 118.8(2)°, respectively. The length of the bond C15-N16 = 1.149(3) Å and the angle of the bond C5-C15-N16 = 178.9(2)°, shows linear character of the carbonitrile group, a characteristic observed in carbonitrile compounds [27]. The values of the C-O bonds (C7A-O7 = 1.374(2) Å, C6-O7 = 1.377(2) Å) in the pyran ring are in good agreement with the value of the literature and the related structure [23-26]. The bond distances C3-C3A = 1.380(3), N1- C7A = 1.320(3), C3-N2 = 1.355(3) Å in the pyrazole ring and C6- C5 = 1.354(3), C5-C4 = 1.526(3), C4-C3A = 1.500(3) Å in the pyran ring also agree well with the standard values [22] and with some related structures [23-26]. Furthermore, C4-C8 = 1.526(3) Å conveys the presence of a single C-C bond. Some other important torsion angles are given in Table 4. Intermolecular interactions are responsible for the stability of molecules within the unit cell. A pair of intermolecular N17- H171···N1 and N17-H172···N16 hydrogen bonds link the molecules to inversion dimers that generate R22(23) graph-set motifs for N-H···N interactions [28,29] (Figure 2). These dimers are arranged in a manner to form chains of rings parallel to the (110) direction. 146 Sharma et al. / European Journal of Chemistry 15 (2) (2024) 143-148 2024 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.15.2.143-148.2525 Table 4. Torsion angles for the title compound. A B C D Angle (°) A B C D Angle (°) N1 N2 C3 C3A -0.1(2) C5 C4 C8 C13 47.0(3) N1 N2 C3 C14 179.74(18) C5 C6 O7 C7A -1.1(3) N2 N1 C7A C3A 0.6(2) C6 C5 C15 N16 152(14) N2 N1 C7A O7 -179.32(17) C6 O7 C7A N1 -176.90(18) N2 C3 C3A C4 -179.6(2) C6 O7 C7A C3A 3.2(3) N2 C3 C3A C7A 0.5(2) C7A N1 N2 C3 -0.3(2) C3 C3A C4 C5 177.0(2) C7A C3A C4 C5 -3.1(3) C3 C3A C4 C8 -60.4(3) C7A C3A C4 C8 119.5(2) C3 C3A C7A N1 -0.7(2) C8 C4 C5 C6 -117.6(2) C3 C3A C7A O7 179.20(19) C8 C4 C5 C15 62.7(2) C3A C4 C5 C6 5.2(3) C8 C9 C10 C11 -0.2(3) C3A C4 C5 C15 -174.55(18) C9 C8 C13 C12 -0.7(3) C3A C4 C8 C9 106.9(2) C9 C10 C11 C12 0.0(4) C3A C4 C8 C13 -72.2(2) C10 C11 C12 C13 -0.1(3) C4 C3A C7A N1 179.32(18) C11 C12 C13 C8 0.5(3) C4 C3A C7A O7 -0.7(3) C13 C8 C9 C10 0.6(3) C4 C5 C6 O7 -3.4(3) C14 C3 C3A C4 0.5(4) C4 C5 C6 N17 175.4(2) C14 C3 C3A C7A -179.4(2) C4 C5 C15 N16 -28(14) C15 C5 C6 O7 176.31(18) C4 C8 C9 C10 -178.52(18) C15 C5 C6 N17 -4.9(3) C4 C8 C13 C12 178.39(18) N17 C6 O7 C7A 179.87(17) C5 C4 C8 C9 -134.0(2) Table 5. Geometry of intermolecular interactions of the title compound. D–H···A D–H, Å H···A, Å D···A, Å θ (D–H···A), ° N17-H171···N1 i 0.89(2) 2.20 3.080(3) 171.6 N17-H172···N16 ii 0.92(2) 2.17 3.079(3) 171 N2-H2···Cg3 iii 0.92(3) 2.55 3.38(2) 149 Symmetry codes: (i) –x-1, -y+1, -z; (ii) -x, -y+1, -z+1; (iii) -x, -y+2, -z. Table 6. Geometry of π-π interactions for the title compound *. CgI CgJ CgI···CgJ, Å CgI···P, Å α, ° β, ° Δ, Å Cg1 Cg2i 3.523 3.444 1.81 10.38 0.74 * Symmetric code: (i) -x, 1-y, -z. Cg1 represents the center of gravity of the pyrazole ring, and Cg2 represents the center of gravity of the pyran ring. CgI···CgJ represents the distance between the ring centroid; CgI···P represents the perpendicular distance of the centroid of one ring from the plane of the other; α is the dihedral angle between the planes of rings I and J; β is the angle between the normal to the centroid of ring I and the line joining the ring centroids; Δ is the displacement of the centroid of rings J relative to the intersection point of the normal to the centroid of ring I and the least squares plane of ring J. Figure 2. Dimer structure of the title compound. Symmetry codes: (i) -x, 1-y, 1-z; (ii) 1-x, 1-y, 2-z. Furthermore, molecules are reinforced by π…π interaction between pyrazole and pyran rings (I and J): the distance between the ring centroids Cg1···Cg2 (-x, 1-y, -z) is 3.523 Å; the perpendicular distance of the centroid of ring I from the plane of ring J (CgI···P is 3.444 Å); the dihedral angle between the planes of rings (α is 1.81°); the angle between normal to the centroid of ring I and the line joining ring centroids (β is 10.38°); and the displacement of the centroid of ring J relative to the intersection point of the normal to the ring I and the least squares plane of ring J (Δ is 0.74 Å). The geometry of N−H···N and N−H···π type of intermolecular hydrogen bonding is given in Table 5. Crystal packing analysis showed that there exist intermolecular hydrogen bonds of N-H···N and N-H···π type, along with π-π interactions; which play an important role in crystal structure stabilization. The pack view of molecules within the unit cell was generated using OLEX2 [30] and is viewed down to the a-axis as shown in Figure 3. The molecules are organized in the crystal lattice, forming ladder-like patterns. The geometry of these interactions is presented in Tables 5 and 6. Sharma et al. / European Journal of Chemistry 15 (2) (2024) 143-148 147 2024 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.15.2.143-148.2525 Figure 3. Packing view of molecules down to the a axis for hydrogen interactions. 4. Conclusion The biologically important scaffold, 6-amino-3-methyl-4- phenyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile, was synthesized using DMSO as a solvent under ambient conditions, and characterized by means of single X-ray crystallographic studies in order to elucidate the crystal structure and understand the behavior of the title molecule in the presence of different hydrogen bond modes and π···π interactions stabilization. Intermolecular interactions are responsible for the stability of molecules within the unit cell. Acknowledgements Vivek Kumar Gupta thanks the University of Jammu, Jammu, India, for financial support. Supporting information CCDC-971311 contains the supplementary crystallographic data for this article. These data can be obtained free of charge via https://www.ccdc.cam. ac.uk/structures/, or by e-mailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(0)1223-336033. Disclosure statement Conflict of interest: The authors declare that they have no conflict of interest. Author contributions: All authors contributed equally to this work. Ethical approval: All ethical guidelines have been adhered to. Sample availability: Samples of the compound are available from the author. CRediT authorship contribution statement Conceptualization: Naresh Sharma, Indrajit Karmakar, Goutam Brahmachari, Vivek Kumar Gupta; Methodology: Naresh Sharma, Indrajit Karmakar, Goutam Brahmachari, Vivek Kumar Gupta; Software: Naresh Sharma, Indrajit Karmakar, Goutam Brahmachari, Vivek Kumar Gupta; Validation: Naresh Sharma, Indrajit Karmakar, Goutam Brahmachari, Vivek Kumar Gupta; Formal Analysis: Naresh Sharma, Indrajit Karmakar, Goutam Brahmachari, Vivek Kumar Gupta; Investigation: Naresh Sharma, Indrajit Karmakar, Goutam Brahmachari, Vivek Kumar Gupta; Resources: Naresh Sharma, Indrajit Karmakar, Goutam Brahmachari, Vivek Kumar Gupta; Data Curation: Naresh Sharma, Indrajit Karmakar, Goutam Brahmachari, Vivek Kumar Gupta; Writing - Original Draft: Naresh Sharma, Indrajit Karmakar, Goutam Brahmachari, Vivek Kumar Gupta; Writing - Review and Editing: Naresh Sharma, Indrajit Karmakar, Goutam Brahmachari, Vivek Kumar Gupta; Visualization: Naresh Sharma, Indrajit Karmakar, Goutam Brahmachari, Vivek Kumar Gupta; Supervision: Naresh Sharma, Indrajit Karmakar, Goutam Brahmachari, Vivek Kumar Gupta; Project Administration: Naresh Sharma, Indrajit Karmakar, Goutam Brahmachari, Vivek Kumar Gupta. ORCID and Email Naresh Sharma nareshbasotra@gmail.com https://orcid.org/0000-0002-1128-880X Indrajit Karmakar ijk91.chem@gmail.com https://orcid.org/0000-0002-2713-8080 Goutam Brahmachari brahmg2001@yahoo.co.in https://orcid.org/0000-0001-9925-6281 Vivek Kumar Gupta vivek.gupta2k9@gmail.com https://orcid.org/0000-0003-2471-5943 References [1]. Nasr, M. N.; Gineinah, M. M. Pyrido [2, 3-d]pyrimidines and Pyrimido[5′, 4′:5, 6]pyrido[2, 3-d]pyrimidines as New Antiviral Agents: Synthesis and Biological Activity. Arch. Pharm. (Weinheim) 2002, 335, 289–295. [2]. Ismail, Z. H., Aly, G. M.; El-Degwi, M. S.; Heiba, H. I.; Ghorab, M. M. Synthesis and insecticidal activity of some new pyranopyrazoles, pyrazolopyranopyrimidines, and pyrazolopyranopyridines. Egypt. J. Biotechnol. 2003, 13, 73–82. [3]. Abdelrazek, F. M.; Metz, P.; Metwally, N. H.; El-Mahrouky, S. F. Synthesis and molluscicidal activity of new cinnoline and pyrano [2,3- c]pyrazole derivatives. Arch. Pharm. 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[30]. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 2009, 42, 339–341. Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry). https://doi.org/10.3389/fchem.2014.00078 https://www.jofamericanscience.org/journals/am-sci/am1010/041_27380am101014_284_294.pdf https://www.jofamericanscience.org/journals/am-sci/am1010/041_27380am101014_284_294.pdf https://www.eurjchem.com/index.php/eurjchem/terms http://creativecommons.org/licenses/by-nc/4.0 https://www.eurjchem.com/index.php/eurjchem/terms 1. Introduction 2. Experimental 2.1. Synthesis of 6-amino-3-methyl-4-phenyl-2,4-dihydro pyrano[2,3-c]pyrazole-5-carbonitrile (5) 2.2. Synthesis of single crystal 2.3. Crystal structure determination and refinement 3. Results and discussion 4. Conclusion Acknowledgements Supporting information Disclosure statement CRediT authorship contribution statement ORCID and Email References PrintField10: PrintField11: PrintField12: PrintField13: PrintField14: PrintField15: PrintField20: PrintField21: PrintField22: PrintField23: PrintField24: PrintField25: