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Crystal structure of 1–methyl-3-propyl-4-nitro-1H-pyrazole-5-carboxylic acid, C8H11N3O4

  • Wen-Chao Fang , Xiao-Fei Liao , Yuan-Zhen Xiong , Ping Zhao EMAIL logo and Jian-Ping Huang ORCID logo EMAIL logo
Published/Copyright: May 7, 2024
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 239 Issue 4

Abstract

[C8H11N3O4], monoclinic, P21/c (no. 14), a = 4.5811(16) Å, b = 19.734(7) Å, c = 11.812(4) Å, β = 101.181(11)°, V = 1047.6(6) Å3, Z = 4, Rgt (F) = 0.0742, wRref (F 2) = 0.1176, T = 296(2) K.

Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colorless block
Size: 0.23 × 0.17 × 0.15 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.11 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 25.5°, >99 %
N(hkl)measured, N(hkl)unique, R int: 7790, 1955, 0.046
Criterion for I obs, N(hkl)gt: I obs > 2σ (I obs), 1221
N(param)refined: 153
Programs: Bruker, 1 SHELX, 2 , 3 Diamond 4
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z U iso*/U eq
O1 1.3410 (6) 0.29653 (15) 0.5133 (2) 0.1072 (10)
O2 1.1428 (5) 0.25361 (12) 0.65278 (19) 0.0834 (8)
H2 1.2933 0.2682 0.6947 0.100*
O3 1.2302 (7) 0.11401 (14) 0.6067 (2) 0.1158 (11)
O4 0.8442 (7) 0.05339 (15) 0.5592 (3) 0.1226 (12)
N1 0.7795 (5) 0.24700 (12) 0.3729 (2) 0.0588 (7)
N2 0.5908 (6) 0.20091 (13) 0.3140 (2) 0.0657 (8)
N3 0.9850 (8) 0.10356 (14) 0.5508 (2) 0.0730 (8)
C1 1.1680 (8) 0.26039 (16) 0.5468 (3) 0.0620 (9)
C2 0.9445 (6) 0.21973 (14) 0.4667 (2) 0.0513 (7)
C3 0.8591 (7) 0.15316 (14) 0.4669 (2) 0.0541 (8)
C4 0.6380 (7) 0.14301 (16) 0.3702 (3) 0.0621 (9)
C5 0.4728 (10) 0.0812 (2) 0.3225 (3) 0.0988 (14)
H5A 0.6046 0.0431 0.3457 0.119*
H5B 0.3079 0.0763 0.3624 0.119*
C6a 0.357 (6) 0.0728 (9) 0.2066 (14) 0.098 (7)
H6Aa 0.4739 0.0995 0.1626 0.118*
H6Ba 0.1557 0.0904 0.1904 0.118*
C7 0.3516 (12) −0.0017 (2) 0.1644 (4) 0.146 (2)
H7A 0.2733 −0.0273 0.2205 0.175*
H7B 0.1920 0.0151 0.1076 0.175*
H7C 0.4746 −0.0301 0.1286 0.175*
C8 0.7637 (8) 0.31731 (15) 0.3345 (3) 0.0776 (11)
H8A 0.9562 0.3317 0.3233 0.116*
H8B 0.7015 0.3454 0.3919 0.116*
H8C 0.6229 0.3212 0.2632 0.116*
C6Ab 0.560 (4) 0.0547 (5) 0.2206 (10) 0.100 (4)
H6AAb 0.597 (13) 0.080 (3) 0.154 (4) 0.149*
H6ABb 0.754 (8) 0.040 (3) 0.262 (5) 0.149*

  1. aOccupancy: 0.35(2), bOccupancy: 0.65(2).

1 Source of materials

To a stirred solution of 65 % concentrated nitric acid (120 mL) and 98 % concentrated sulfuric acid (180 mL) was added 1-methyl-3-propyl-1H-pyrazole-5-carboxylic acid (38.62 g, 0.23 mol). After heated at 100 °C for 16 h, the reaction was completed (monitored by TLC). The reaction solution was poured into ice water (200 mL), and the white precipitate appeared. The solid precipitate was collected by vacuum filtration and crystallized from acetone to obtain 1-methyl-4-nitro-3-propyl-1H-pyrazole-5-carboxylic acid in 79.6 % yield. 1H (400 MHz)and 13C (100 MHz) NMR spectra of 1-methyl-4-nitro-3-propyl-1H-pyrazole-5-carboxylic acid were recorded on a Bruker Avance 400 spectrometer in CDCl3 using tetramethylsilane (TMS) and CDCl3 (13C, δ 77.0 ppm) as internal standards. J-values were given in Hertz. 1 H NMR (400 MHz, CDCl3): δ = 0.99–1.03 (t, J = 8.0 Hz, 3H, CH2CH3), 1.68–1.77 (m, 2H, CH2CH3), 2.86–2.90 (t, J = 8.0 Hz, 2H, CH2C=N), 4.14 (s, 3H, N–CH3), 8.38 (br, 1 H, COOH) ppm. 13 C NMR (100 MHz, CDCl3): δ = 158.58, 149.81, 132.33, 130.87, 40.63, 29.08, 21.25, 13.79 ppm.

2 Experimental details

All H atoms were included in calculated positions and refined as riding atoms, with C–H = 0.90–0.97 Å with U iso(H) = 1.5 U eq(C) for methyl H atoms and 1.2 U eq(C) for all other H atoms.

3 Comment

Having been developed by Pfizer and first come into the market in the United States in April 1998, Sildenafil (trade name: Viagra) is a highly selective and specific phosphodiesterase type 5 inhibitor (PDE5i) to treat erectile dysfunction (ED), 5 , 6 to protect the heart and lungs to enhance the vitality of the body, to treat pulmonary hypertension, 7 – 9 and to promote left ventricular function and cardiopulmonary performance. 10 , 11 Nowadays, the synthesis and modification of Sildenafil have also attracted wide attention from chemical workers. Recently, an impactful and high-yielding method for the synthesis of Sildenafil has been developed in our group, and single crystals of several key intermediates have been achieved, and the using of the key intermediates as catalytic agents has been also explored.

In the molecule of the title compound bond lengths and angles within 1-methyl-3-propyl-4-nitro-1H-pyrazole-5-carboxylic acid are very similar to those given in the literature. 12 – 14 The propyl group in the molecule is disordered. The dihedral angles between the pyrazole ring, the O1–C1–O2 carboxyl group and the nitro group are 48.8°, 21.3° and 52.239(364)°, respectively. The torsion angles of C3–C4–C5–C6, C3–C4–C5–C6A, C4–C5–C6–C7 and C4–C5–C6A–C7 are −151.9°, −106.3°, 148.2° and −171.0°, respectively. Intermolecular O–H⋯N hydrogen bonds between oxygen atom (O2) of carboxyl group and nitrogen atoms (N2) of pyrazole ring connect the adjacent title compound to form a one dimensional chain. In addition, there also exist weak Intermolecular C–H⋯O hydrogen bonds, which contributes to the stability of the crystal structure.

Corresponding authors: Ping Zhao, College of Materials and Chemical Engineering, Southwest Forestry University, Kunming 650224, P.R. China, E-mail: ; and Jian-Ping Huang, College of Chemistry and Materials, Jiangxi Agricultural University, Nanchang 330045, P.R. China; and Key Laboratory of Chemical Utilization of Plant Resources of Nanchang, Nanchang Tangteng Science and Technology Ltd, Nanchang 330045, P.R. China; and Jiangxi Jiren Linhua Industrial Co., Ltd, Chongren 344200, P.R. China; and Jiangxi Longyuan Chemical Industry Co., Ltd, Zhangshu 331200, P.R. China, E-mail:

Funding source: Natural Science Foundation of Science and Technology Department of Jiangxi Province

Award Identifier / Grant number: 20151BBF60081; 20171BBE50027; 20171BBG70029; 20202BBEL53028

Funding source: Science and Technology Research Project of Education Department of Jiangxi Province

Award Identifier / Grant number: GJJ170275

Funding source: Natural Science Foundation of Nanchang City

Award Identifier / Grant number: 2018CXTD014

Funding source: Natural Science Foundation of Fuzhou City, Jiangxi Province

Award Identifier / Grant number: 202205127297

Funding source: Natural Science Foundation of Jiangxi Agriculture University

Award Identifier / Grant number: 09004634; 09005194; 201610410007; 201610410079; 2022JXAUHX128

Funding source: 2021 Innovation Team Project of Ji’an City, Jiangxi Province

Acknowledgments

X-ray data were collected at Instrumental Analysis Center Nanchang Hangkong University, Nanchang, 330063, People’s Republic of China.

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This study was supported by grants from Natural Science Foundation of Science and Technology Department of Jiangxi Province (No. 20151BBF60081; 20171BBE50027; 20171BBG70029; 20202BBEL53028), Science and Technology Research Project of Education Department of Jiangxi Province (No. GJJ170275), Natural Science Foundation of Nanchang City (No. 2018CXTD014), Natural Science Foundation of Fuzhou City, Jiangxi Province (No. 202205127297), Natural Science Foundation of Jiangxi Agriculture University (No. 201610410007; 201610410079; 2022JXAUHX128), 2021 Innovation Team Project of Ji’an City, Jiangxi Province and 2023 “Jie Bang Gua Shuai” Project of Fuzhou City, Jiangxi Province.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2024-03-06
Accepted: 2024-04-11
Published Online: 2024-05-07
Published in Print: 2024-08-27

© 2024 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  4. The crystal structure of poly[((2-(4,5-dihydro-1H-pyrazol-4-yl)-1,3-dioxoisoindoline-5-carbonyl)oxy)(1-(dimethylamino)ethoxy)zinc[II]], C16H14ZnN4O5
  5. Crystal structure of bis[(triaqua-4-iodopyridine-2,6-dicarboxylato-κ 3 N,O,O ″)cobalt(II)] trihydrate, C14H22N2O17I2Co2
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https://doi.org/10.1515/ncrs-2024-0114
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of hexaquazinc(II) poly[hexakis(μ2-4-methylbenzenesulfinato-κ2O:O′) dizinc(II)]
  4. The crystal structure of poly[((2-(4,5-dihydro-1H-pyrazol-4-yl)-1,3-dioxoisoindoline-5-carbonyl)oxy)(1-(dimethylamino)ethoxy)zinc[II]], C16H14ZnN4O5
  5. Crystal structure of bis[(triaqua-4-iodopyridine-2,6-dicarboxylato-κ 3 N,O,O ″)cobalt(II)] trihydrate, C14H22N2O17I2Co2
  6. Crystal structure of bis(methanol-κO)-bis(nitrato-kO)-bis(1-((2-(2-chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolan-2-yl)methyl)-1H-1,2,4-triazole-κN)cadmium(II), C40H42O14N8Cl4Cd
  7. Crystal structure of poly[μ2-dichlorido-(μ2-1-[(2,4-dimethyl-1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2N:N′)cadmium(II)], C11H12CdN6Cl2
  8. The crystal structure of (3aS, 4R, 7S, 7aR)-hexahydro-4, 7-methano-1H-isoindole-1, 3-(2H)-dione, C9H11NO2
  9. The crystal structure of N-(acridin-9-yl)-4-chloro-N-(4-chloro-butanoyl) butanamide, C21H20Cl2N2O2
  10. Crystal structure of 3,3′-dimethoxy-4,4′-oxy-di-benzaldehyde, C16H14O5
  11. The crystal structure of tetrakis(μ 2-2-amino-3,5-dibromobenzoate-κ 2 O:O′)-octakis(n-butyl-κ 1 C)-bis(μ 3-oxo)tetratin(II), C60H92Br8N4O10Sn4
  12. Crystal structure of methyl-1-(naphthalen-1-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H20N2O2
  13. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  14. Crystal structure of 6,6′-((1E,1′E)-((2-phenylpyrimidine-4,6-diyl)bis(hydrazin-2-yl-1-ylidene))bis(methaneylylidene))bis(2-methoxyphenol)monohydrate, C26H26N6O5
  15. Crystal structure of bis(N,N,N-trimethylbutanaminium) tetrathiotungstate(VI), (BuMe3N)2[WS4]
  16. The crystal structure of 2,3,9-triphenyl-9-(2-phenylbenzofuran-3-yl)-9H-9λ 5-benzo[4,5][1,2]oxaphospholo[2,3-b][1,2,5]oxadiphosphole 2-oxide, C40H28O4P2
  17. Crystal structure of 1–methyl-3-propyl-4-nitro-1H-pyrazole-5-carboxylic acid, C8H11N3O4
  18. Crystal structure of N-(benzo[d]thiazol-2-yl)-2-chloroacetamide, C9H7ClN2OS
  19. The crystal structure of N-benzyl-2-chloro-N-(p-tolyl) acetamide, C16H16ClNO
  20. Crystal structure of 3,4-dimethoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H24O5
  21. Crystal structure of 2,5-bis(2,5-dimethoxybenzyl)-3,6-dimethyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione, C26H28N2O6
  22. Crystal structure of poly[(μ3-5-bromoisophthalato-κ4 O,O′ :O″,O‴)-(μ2-1,2-bis(1,2,4-triazole-1-ylmethyl)benzene-κ2 N:N′)cobalt(II)], C20H15BrCoN6O4
  23. The crystal structure of bis(2-(piperidin-1-ium-4-yl)-1Hbenzo[d]imidazol-3-ium) dihydrogen decavanadate, C24H36N6O28V10
  24. Crystal structure of diaqua-bis(1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine3-carboxylato-O,O′)-cobalt(ii)dihydrate, C26H36N4O14Co
  25. Crystal structure of poly[(μ2-5-bromoisophthalato-κ4 O,O ′:O ″,O ‴)-(μ2-1,4-bis(2-methylimidazol-1-ylmethyl)benzene-N:N′)cadmium(II)], C24H21BrCdN4O4
  26. The crystal structure of dimethyl 8-(3-methoxy-2-(methoxycarbonyl)-3-oxoprop-1-en-1-yl)-4-methyl-1-(p-tolyl)-1,3a,4,8b-tetrahydro-3H-furo[3,4-b]indole-3,3-dicarboxylate. C28H29NO9
  27. Crystal structure of (3R)-1-(3,5-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate chloride, C21H23ClN2O4
  28. Synthesis and crystal structure of 3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)benzoic acid, C12H13NO5S
  29. The crystal structure of hexaaquamagnesium(II) bis-3-(1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-α]pyridin-1-yl)benzoate, C36H42N4O10Mg
  30. Crystal structure of 4-formyl-2-methoxyphenyl 2-acetoxybenzoate, C17H14O6
  31. Crystal structure of poly[octakis(μ-oxido)-tris(μ-1,1′-[[1,1′-biphenyl]-4,4′-diylbis(methylene)]bis(1H-imidazole))-tetrakis(oxido)-tetra-vanadium-dimanganese(II)dihydrate], C30H29MnN6O7V2
  32. Crystal structure of 4,8a-bis(4-chlorophenyl)-1,5,6-tris(4-fluorobenzyl)-1,4,4a,4b,5,6,8a,8b-octahydrocyclobuta[1,2-b:3,4-c′]dipyridine-3,8-dicarbonitrile, C45H33Cl2F3N4
  33. Crystal structure of benzo[d][1,3]dioxol-5-ylmethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H20O5
  34. Crystal structure of N-benzoyl-N-phenylhydroxylaminato-dicarbonylrhodium(I), [Rh(BNA)CO2]
  35. The crystal structure of N-(2-((2-methoxynaphthalen-1-yl)ethynyl)phenyl)-4-methylbenzenesulfonamide, C26H21NO3S
  36. The crystal structure of methyl ((4-aminobenzyl)sulfonyl)-d-prolinate, C13H18N2O4S
  37. The crystal structure of dichlorido-(N-isopropyl-N-(pyridin-2-ylmethyl)propan-2-amine-κ 2 N, N′)palladium(II), C12H20N2PdCl2
  38. Crystal structure of poly[(μ 2-5-hydroxyisophthalato-κ4 O,O′:O″,O‴)-(μ 2-1,4-bis(2-methylimidazolyl)-1-butene-N:N′)nickel(II)], C20H20NiN4O5
  39. The crystal structure of {hexakis(1-methyl-1H-imidazole-κ 1 N)cobalt(II)}(μ 2-oxido)-hexaoxido-dimolybdenum(VI)— 1-methyl-1H-imidazole (1/2), C32H48CoMo2N16O7
  40. Synthesis, crystal structure and nonlinear optical property of 1-((propan-2-ylideneamino)oxy)propan-2-yl-4-methylbenzenesulfonate, C13H19O4NS
  41. The crystal structure of N,N-(ethane-1,1-diyl)dibenzamide, C16H16N2O2
  42. Crystal structure of 1-(4-bromophenyl)-3-(diphenylphosphoryl)-3-hydroxypropan-1-one, C21H18BrO3P
  43. The crystal structure of fac-tricarbonyl(bis(3,5-dimethyl-4H-pyrazole)-κ1 N)-((nitrato)-κ1 O)-rhenium(I)— 3,5-dimethyl-4H-pyrazole(1/1), C18H23N7O6Re
  44. The crystal structure of 4′-chloro-griseofulvin: (2S,6′R)-4′,7-dichloro-4,6-dimethoxy-6′-methyl-3H-spiro[benzofuran-2,1′-cyclohexan]-3′-ene-2′,3-dione, C16H14Cl2O5
  45. Crystal structure of tetraethylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  46. Crystal structure of 1-cyclohexyl-4-p-tolyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester, C22H27NO4
  47. The crystal structure of catena-poly(μ2-1,4-bis-(1H-imidazol-1-yl)benzene-copper(I)) dichloridocopper(I), {[CuC12H10N4]+[CuCl2]−} n
  48. The crystal structure of propane-1-aminium-2-carbamate, C4H10N2O2
  49. Crystal structure of 5,6,3′,4′,5′-pentamethoxy-flavone dihydrate, C20H24O9
  50. Crystal structure of (E)-N-(2-bromophenyl)-4-(4-(3,5-dimethoxystyryl)phenoxy)pyrimidin-2-amine, C26H22BrN3O3
  51. Crystal structure of methyl (3R)-1-(2-bromo-4-fluorophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride hydrate, C19H19BrClFN2O3
  52. The crystal structure of 1-(2-chlorophenyl)-3-(p-tolyl)urea, C14H13ClN2O
  53. The crystal structure of 1-cyclohexyl-3-(p-tolyl)urea, C14H20N2O
  54. Crystal structure of ((benzyl(hydroxy)-amino)(4-chlorophenyl)methyl)-diphenylphosphine oxide, C26H23ClNO2P
  55. The crystal structure of ethyl 3-(1-methyl-1H-indole-2-carbonyl)-2-phenylquinoline-4-carboxylate, C28H22N2O3
  56. The crystal structure of 1,4-bis(1H-imidazol-3-ium-1-yl)benzene dinitrate, C12H12N4 2+·2(NO3 −)
  57. Crystal structure of tris(hexafluoroacetylacetonato-κ2O,O′) bis(triphenylphosphine oxide-κ1O)samarium(III), C51H33F18O8P2Sm
  58. Crystal structure of 1-(4-(dimethylamino)phenyl)-2,3-bis(diphenylphosphoryl)propan-1-one, C35H33NO3P2
  59. Crystal structure of diaqua[bis(μ 2-pyridine 2,6-dicarboxylato) bismuth(III) potassium(I)], C14H10BiKN2O10
  60. Crystal structure of (R)-N, N ′-dimethyl-[1, 1′-binaphthalene]-2, 2′-diamine, C22H20N2
  61. Crystal structure of 1-phenyl-4-(2-furoyl)-3-furyl-1H-pyrazol-5-ol, C18H12N2O4
  62. Crystal structure of bis(14,34-dimethyl[11,21:23,31-terphenyl]-22-yl)diselane, C40H34Se2
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