Home Physical Sciences Crystal structure of N-(4-bromobenzyl)-3-(difluoromethyl)-1-methyl-N-(pyridin-2-yl)-1H-pyrazole-4-carboxamide, C18H15BrF2N4O
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Crystal structure of N-(4-bromobenzyl)-3-(difluoromethyl)-1-methyl-N-(pyridin-2-yl)-1H-pyrazole-4-carboxamide, C18H15BrF2N4O

  • Ya-Li Liu , Hua-Jin Zhang , Juan Luo , Shang-Xing Chen ORCID logo EMAIL logo and Ji Zhang ORCID logo EMAIL logo
Published/Copyright: January 15, 2024
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 239 Issue 2

Abstract

C18H15BrF2N4O, monoclinic, C2/c (no. 15), a = 22.984(4) Å, b = 10.0726(16) Å, c = 16.551(3) Å, β = 107.972(2)°, V = 3644.8(10) Å3, Z = 8, Rgt(F) = 0.0412, wRref(F2) = 0.1051, T = 296(2) K.

CCDC no.: 2321869

The molecular structure is shown in the figure. 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: 0.20 × 0.15 × 0.14 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 2.29 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 25.5°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 13,255, 3390, 0.045
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 2181
N(param)refined: 237
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 Uiso*/Ueq
C1 0.16762 (15) 0.7552 (3) 0.28637 (19) 0.0601 (8)
H1 0.1951 0.7739 0.3395 0.072*
C2 0.11871 (16) 0.8397 (3) 0.2521 (2) 0.0648 (9)
H2 0.1133 0.9147 0.2817 0.078*
C3 0.07848 (14) 0.8111 (3) 0.1739 (2) 0.0579 (8)
C4 0.08649 (14) 0.7021 (3) 0.1292 (2) 0.0599 (8)
H4 0.0592 0.6839 0.0758 0.072*
C5 0.13554 (14) 0.6198 (3) 0.16443 (19) 0.0535 (8)
H5 0.1412 0.5459 0.1340 0.064*
C6 0.17631 (13) 0.6437 (3) 0.24321 (17) 0.0464 (7)
C7 0.22571 (14) 0.5432 (3) 0.2794 (2) 0.0577 (8)
H7A 0.2078 0.4671 0.2988 0.069*
H7B 0.2415 0.5132 0.2346 0.069*
C8 0.28921 (13) 0.5241 (3) 0.42894 (18) 0.0437 (7)
N1 0.24392 (14) 0.5203 (3) 0.4606 (2) 0.0771 (9)
C12 0.2534 (3) 0.4499 (5) 0.5317 (4) 0.1080 (16)
H12 0.2216 0.4449 0.5552 0.130*
C11 0.3057 (3) 0.3854 (5) 0.5722 (3) 0.1023 (16)
H11 0.3096 0.3378 0.6217 0.123*
C10 0.3519 (2) 0.3918 (4) 0.5391 (3) 0.0928 (13)
H10 0.3888 0.3496 0.5659 0.111*
C13 0.31674 (13) 0.6772 (3) 0.33157 (18) 0.0482 (7)
C14 0.36331 (12) 0.7445 (3) 0.40087 (17) 0.0434 (7)
C15 0.36056 (13) 0.7901 (3) 0.47766 (18) 0.0484 (7)
H15 0.3289 0.7757 0.5005 0.058*
C16 0.41965 (12) 0.7925 (3) 0.39641 (18) 0.0456 (7)
C17 0.44625 (15) 0.7774 (3) 0.3256 (2) 0.0614 (9)
H17 0.4282 0.7004 0.2905 0.074*
C18 0.42850 (17) 0.9286 (4) 0.5948 (2) 0.0778 (11)
H18A 0.3922 0.9602 0.6057 0.117*
H18B 0.4544 1.0025 0.5929 0.117*
H18C 0.4499 0.8690 0.6392 0.117*
F1 0.50773 (9) 0.7643 (2) 0.35612 (14) 0.0866 (6)
F2 0.43681 (12) 0.8889 (2) 0.27754 (16) 0.1063 (9)
C9 0.34422 (16) 0.4614 (3) 0.4654 (2) 0.0661 (9)
H9 0.3754 0.4661 0.4406 0.079*
N2 0.27710 (11) 0.5923 (2) 0.35049 (14) 0.0478 (6)
N3 0.41167 (11) 0.8591 (3) 0.51367 (15) 0.0522 (6)
N4 0.44917 (11) 0.8612 (3) 0.46532 (17) 0.0540 (6)
O1 0.31226 (11) 0.7041 (2) 0.25761 (14) 0.0727 (7)
Br1 0.01111 (2) 0.92581 (4) 0.12561 (3) 0.0921 (2)

1 Source of materials

3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (1.76 g, 10.0 mmol), thionyl chloride (30.0 mmol) and N,N-dimethylformamide (0.5 mL) were reacted at 95 °C for 4 h. At the end of the reaction, the excess thionyl chloride was distilled away to obtain 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride, which was dissolved in dichloromethane solution (30.0 mL). Then, N-(4-bromobenzyl)pyridin-2-amine (2.62 g, 10.0 mmol), triethylamine (2.02 g, 20.0 mmol) and dichloromethane (30.0 mL) were added into 100 mL single neck bottle, cooled to 0 °C, and the dichloromethane solution of 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride parts was slowly added under stirring conditions. After addition, the reaction solution was stirred at room temperature for 6 h, and the reaction was monitored by thin-layer chromatography (TLC). After the reaction is over, silica gel was added and fully mixed. Column chromatography (V[petroleum ether]:V[ethyl acetate] = 1:2) was used to elute and purify the final product N-(4-bromobenzyl)-3-(difluoromethyl)-1-methyl–N-(pyridin-2-yl)-1H-pyrazole-4-carboxamide (1.46 g), which was a light yellow solid with a yield of 58.0 %.

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 Uiso(H) = 1.5 Ueq(C) for methyl H atoms and 1.2 Ueq(C) for all other H atoms.

3 Comment

Nitrogen-containing heterocyclic compounds have gained significant attention as crucial intermediates in the synthesis of numerous pharmaceutical drugs [5, 6]. Pyrazole amides, as a significant class of nitrogen-containing heterocyclic compounds, serve as fundamental structural frameworks for numerous drug molecules [7, 8]. They encompass a wide range of pharmacological effects, making them vital in the fields of pesticides and medicine [9, 10]. Therefore, in recent years, the synthesis of pyrazole amide compounds and the investigation of their biological activity have garnered increasing attention from the scientific community. For instance, Zhong et al. have designed and synthesized 36 novel pyridine ring pyrazolamide derivatives with the help of active substructure splicing strategy [11]. Zhong et al. also have reported the structure of 3-(difluoromethyl)-1-methyl–N-(4, 11, 11-trimethyl-1, 2, 3, 4-tetrahydro-1,4-tetrahydro-1,4-methanoacridin-9-yl)-1H-pyrazole-4-carboxamide monohydrate [12]. These reports are all based on amide compounds formed by carboxylic acids and bases, which show different pharmacological effects through different substituents. N-(4-bromobenzyl)-3-(difluoromethyl)-1-methyl–N-(pyridin-2-yl)-1H-pyrazole-4-carboxamide was synthesized by us from 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride and N-(4-bromobenzyl)pyridin-2-amine.

In the molecule of the title compound, bond lengths and angles are very similar to those given in the literature [11–13]. The dihedral angles of the C1–C6 phenyl plane, the pyrazole ring and the pyridine ring plane were 69.3(1)°, 66.3(1)° and 67.3(1)°, respectively. The torsion angles of C5–C6–C7–N2, C6–C7–N2–C8, C6–C7–N2–C13, C7–N2–C13–O1, C7–N2–C13–C14, and N2–C13–C14–C15 are 163.8(3)°, 120.8(3)°, −73.6(3)°, −5.1(4)°, 170.9(3)° and 38.6(4)°, respectively. There are still some weak C–H⋯N, C–H⋯O and C–H⋯F hydrogen bonds in the stacking structure of molecules.

Corresponding authors: Shang-Xing Chen and Ji Zhang, National Forestry and Grassland Bureau Woody Spice (East China) Engineering Technology Research Center; The Institute of Plant Natural Products and Forest Products Chemical Engineering, College of Forestry, Jiangxi Agricultural University, Nanchang 330045, People’s Republic of China, E-mail: (S.-X. Chen), (J. Zhang)

Funding source: Special Funding for Scientific and Technological Research and Development in Jiangxi Province

Award Identifier / Grant number: (No. 20203ABC28W016)

Funding source: Natural Science Foundation of Jiangxi

Award Identifier / Grant number: (No. 20212BAB215012)

Funding source: Special Research Project on CamphorTree (KRPCT) of Jiangxi Forestry Department

Award Identifier / Grant number: (No. 2020CXZX07)

Funding source: Earmarked Fund for the Youthful Innovation Research Team of Jiangxi Agricultural University-05, Innovation Team project of Ji’an City

Award Identifier / Grant number: (No. jasb202310102)

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 work was supported by the Special Funding for Scientific and Technological Research and Development in Jiangxi Province (No. 20203ABC28W016), the Natural Science Foundation of Jiangxi (No. 20212BAB215012), Special Research Project on CamphorTree (KRPCT) of Jiangxi Forestry Department (No. 2020CXZX07) and the Earmarked Fund for the Youthful Innovation Research Team of Jiangxi Agricultural University-05, Innovation Team project of Ji’an City (No. jasb202310102).

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

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Received: 2023-11-22
Accepted: 2023-12-26
Published Online: 2024-01-15
Published in Print: 2024-04-25

© 2023 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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https://doi.org/10.1515/ncrs-2023-0513
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Solvothermal synthesis and crystal structure of aqua-tris(p-acetamidobenzoate-κ2O,O′)-(2,2′-bipyridine-κ2N,N′)terbium(III) - water - methanol (1/1/1)
  4. Crystal structure of hexaaquazinc(II) catena-poly[bis(1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxylato-κ2O,O′)-bis(μ2-1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxylato-κ2O:O′)trizinc(II)] hexahydrate C26H36N4O20Zn2
  5. The crystal structure of valinyl-N-ium-4-(5-(thiophen-2-yl)isoxazol-3-yl)phenyl trifluoroacetate
  6. Crystal structure of bis(3,5-diisopropyl-1H-pyrazol-4-ammonium) tetrafluoroterephthalate, 2[C9H18N3][C8F4O4]
  7. Crystal structure of aqua-octakis(μ3-salicylato)-(1,10-phenanthroline)-(acetonitrile)-dicobalt(II)-trititanium(IV), C70H45N3O25Co2Ti3
  8. Crystal structure of catena-poly[aqua-(μ2-4,4′-diimidazole diphenyl ether-κ2N:N′)-(sulfato-κ1O)-cobalt(II)] – dimethylformamide (2/1), C39H37CoN9O8S
  9. Crystal structure of (5R,8R,9R,10R,12R, 13R,14R,17S)-2-(E-3-fluorobenzylidene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl) hexadecahydro-3H-cyclopenta[a]phenanthren-3-one, C37H53FO3
  10. Crystal structure of (Z)-4-((4,5,6-trimethoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)phenyl diphenylphosphinate, C30H25O7P
  11. Crystal structure of 3-((5-methylpyridin-2-yl)amino)-1-phenylpropan-1-one, C15H16N2O
  12. The crystal structure of (R)-9-(5-methoxy-2-methyl-2,3-dihydro-1H-cyclopenta[a]naphthalen-1-ylidene)-9H-thioxanthene, C28H22OS
  13. Crystal structure of diaqua-bis[1-(1-(hydroxymethyl)-1H-pyrazol-3-yl)-5-methyl-1H-1,2,3-triazole-4-carboxylato-κ2N,O)] manganese(II), C16H20MnN10O8
  14. The crystal structure of t-butyl 7-[4-(4-fluorophenyl)-2-[(methanesulfonyl)(methyl)amino]-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoate, C26H36FN3O6S
  15. The crystal structure of samarium sulfate pentahydrate, Sm2(SO4)3(H2O)5
  16. The crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ 4 N,O,O,O)-zinc(II)] monohydrate, C12H15NO9Zn
  17. The crystal structure of 2,3-difluoro-11H-benzo-[4,5]imidazo[2,1-a]isoindol-11-one, C14H6F2N2O
  18. The crystal structure of 2,3-di(9H-carbazol-9-yl)-9H-fluoren-9-one, C37H22N2O
  19. The crystal structure of 5-(2-chloro-3-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)-10,11-dihydro-5H-dibenzo[b,f]azepine, C40H39ClN2
  20. Crystal structure of 2-bromo-1-hydroxy-3-(3-methylbut-2-enyloxy)-9H-xanthen-9-one, C18H15BrO4
  21. Crystal structure of bis(μ2-benzenesulfonato-κ2O:O′)-bis(μ2-6,6′-((ethane-1,2-diylbis(azaneylylidene))bis(methaneylylidene))-bis(2-methoxyphenolato-κ6O,O′:O′,N,N′,O′′:O′′,O′′′))disodium(I)dicopper(II)
  22. The crystal structure of (E)-1,2-bis(benzo[e][1,2]azaborinin-2(1H)-yl)ethene, C18H16B2N2
  23. Crystal structure of 3-oxo-urs-12-en-28-benzyl ester, C37H52O3
  24. The crystal structure of ethyl (E)-1-chloro-3-(4-chloro-1-methyl-1H-indole-2-carbonyl)-4-oxo-2-phenylcyclooct-2-ene-1-carboxylate, C27H25Cl2NO4
  25. The crystal structure of 4,4′-((5-bromo-2-iodo-1,3-phenylene)bis(oxy))bis(tert-butylbenzene) ─ ethanol (2/1), C26H28BrIO2
  26. Crystal structure of (E)-1-(4-(benzyloxy)-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one, C18H19NO3
  27. The crystal structure of N1,N3-bis(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)\ propanediamide hydrate, C25H26N6O4, 2(H2O)
  28. The crystal structure of 2,5-bis[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)amino]cyclohexa-2,5-diene-1,4-dione, C28H26N6O4
  29. Crystal structure of 3,4-bis[2-(hydroxymethyl)-pyrrolidin-1-yl] cyclobut-3-ene-1,2-dione hydrate, C14H22N2O5
  30. The crystal structure of 2-(3,4–dichlorobenzyl)-1H-benzimidazole, C14H10Cl2N2
  31. The crystal structure of 2-(2-((4,6-dimethoxypyrimidin-2-yl)oxy)phenyl)-4-(piperidin-1-yl)-5H-chromeno[2,3-d]pyrimidine, C28H27N5O4
  32. The crystal structure of 6-(benzofuran-2-yl)-2-oxo-4,5-diphenyl-3,4-dihydro-2H-pyran-3-carbonitrile, C26H17NO3
  33. Crystal structure of N-(4-bromobenzyl)-3-(difluoromethyl)-1-methyl-N-(pyridin-2-yl)-1H-pyrazole-4-carboxamide, C18H15BrF2N4O
  34. The crystal structure of the host-guest complex: N′-{5-[2-(2,6-dimethylphenoxy)acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl}-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide-diethyl ether (2/1)
  35. The crystal structure of (Z)-4-amino-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H17N3O2
  36. The crystal structure of diethyl 1,4-dihydro-2,6-dimethyl-4-(3-cyanophenyl)-3,5-pyridinedicarboxylate, C20H22N2O4
  37. Crystal structure of 3-(5-((4-(difluoromethoxy)phenyl) sulfonyl)-3,4,5,6-tetrahydropyrrolo[3,4-c]pyrrol-2(1H)-yl) oxetane-3-carboxamide, C17H19F2N3O5S
  38. Crystal structure of 2-((2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)amino)-N-(2-(4-methylpiperazin-1-yl)ethyl)benzamide hydrate, C25H37Cl2N5O6
  39. Crystal structure of 3-(benzo[d]thiazol-2-yl)-5-bromo-2-hydroxybenzaldehyde, C14H8BrNO2S
  40. Crystal structure of 3-(difluoromethyl)-1-methyl-N-(pyridin-2-yl)-1H-pyrazole-4-carboxamide, C11H10F2N4O
  41. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-isopropyl-1H-imidazol-3-ium hexafluoridophosphate(V), C20H34F12N4P2
  42. Crystal structure of ethyl 5,6-dichloro-2-methyl-2,3-dihydro-1 H-benzo[d]imidazole-2-carboxylate, C11H12Cl2N2O2
  43. The crystal of structure of (OC-6-22)-pentakis(acetonitrile)bromidoruthenium(II)bromide monohydrate, C10H15Br2N5Ru
  44. Crystal structure of (2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(((4aS,5R,6S)-1-oxo-5-vinyl-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl)oxy)tetrahydro-2H-pyran-3-yl 2,3-dihydroxybenzoate hydrate, C23H26O12·H2O
  45. The crystal structure of (E)-4-amino-N′-(1-(4-fluorophenyl)propylidene)benzohydrazide, C16H16FN3O
  46. The crystal structure of 2′-(9H-carbazol-9-yl)-[1,1′-binaphthalen]-2-amine, C32H22N2
  47. Crystal structure of poly[μ3-diiodido-[μ2-di(1H-pyrazol-1-yl)methane-κ2N,N′)]dicopper(I)], C7H8Cu2I2N4
  48. Crystal structure of 3-amino-N′-hydroxy-1H-pyrazole-4-carboximidamide, C4H7N5O
  49. The crystal structure of 1,3-diacetyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, C8H10O4N4
  50. Crystal structure of catena-poly[aqua-(μ2-1,4-diazabicyclo[2.2.2]octane-k2N: N′)-bis(sorbato-κ1O)-copper(II), C18H28CuN2O5
  51. Crystal structure of catena-poly[triaqua-(μ2 -1-(4-carboxylatophenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylato-κ3O,O′:O′′)manganese(II)], C12H12N2O8Mn
  52. The crystal structure of [hexaaquamagnesium(II)] 4-[(pyridine-4-carbonyl)-amino]-phthalate trihydrate, C14H26N2O14Mg
  53. Crystal structure of 1-(p-tolylphenyl)-4-(2-furoyl)-3-methyl-1H-pyrazol-5-ol, C16H14N2O3
  54. The crystal structure of bis(1,4,7,10,13-pentaoxacyclopentadecane)-potassium(I) dichloridocopper(I), C20H40Cl2CuKO10
  55. The crystal structure of tris(tetra-n-butylammonium) hexanitrato-κ2O,O′-lanthanium(III) C48H108N9O18La
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