Startseite Crystal structure of N-(4′-chloro-[1,1′-biphenyl]-2-yl)formamide, C13H10ClNO
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Crystal structure of N-(4′-chloro-[1,1′-biphenyl]-2-yl)formamide, C13H10ClNO

  • Mo Du , Xiaona Xu und Hongjuan Tong ORCID logo EMAIL logo
Veröffentlicht/Copyright: 12. Juli 2023

Abstract

C13H10ClNO, monoclinic, P21 (no. 4), a = 4.3011(7) Å, b = 11.2236(19) Å, c = 11.776(2) Å, β = 94.281(5)°, V = 566.90(16) Å3, Z = 2, R gt (F) = 0.0420, wR ref (F2) = 0.0827, T = 170 K.

CCDC no.: 2249544

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: 0.12 × 0.08 × 0.05 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.31 mm−1
Diffractometer, scan mode: Bruker D8 VENTURE, φ and ω
θmax, completeness: 26.4°, 98 %
N(hkl)measured, N(hkl)unique, Rint: 5406, 2210, 0.046
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 1683
N(param)refined: 145
Programs: Bruker [1], SHELX [2, 3], Olex2 [4]
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.9103 (9) 0.7277 (3) 0.1815 (4) 0.0374 (10)
C2 0.7480 (9) 0.6985 (3) 0.2735 (4) 0.0378 (10)
H2 0.679136 0.758834 0.322339 0.045*
C3 0.6860 (8) 0.5793 (3) 0.2939 (3) 0.0337 (10)
H3 0.574375 0.558298 0.357605 0.040*
C4 0.7848 (9) 0.4898 (3) 0.2225 (3) 0.0316 (9)
C5 0.9492 (9) 0.5234 (4) 0.1304 (3) 0.0387 (10)
H5 1.018426 0.463738 0.080941 0.046*
C6 1.0148 (10) 0.6419 (4) 0.1091 (4) 0.0401 (10)
H6 1.128772 0.663709 0.046240 0.048*
C7 0.7072 (8) 0.3623 (3) 0.2410 (3) 0.0313 (9)
C8 0.5639 (9) 0.2960 (4) 0.1517 (4) 0.0402 (10)
H8 0.524871 0.332306 0.079197 0.048*
C9 0.4768 (10) 0.1782 (3) 0.1662 (4) 0.0438 (11)
H9 0.378542 0.134733 0.104255 0.053*
C10 0.5339 (9) 0.1246 (4) 0.2713 (4) 0.0418 (11)
H10 0.471985 0.044363 0.282144 0.050*
C11 0.6812 (9) 0.1877 (3) 0.3606 (4) 0.0377 (10)
H11 0.721479 0.150631 0.432734 0.045*
C12 0.7700 (8) 0.3046 (3) 0.3453 (3) 0.0311 (9)
C13 0.8085 (8) 0.4077 (3) 0.5280 (3) 0.0349 (10)
H13 0.941877 0.440281 0.588045 0.042*
Cl1 0.9912 (3) 0.87769 (10) 0.15545 (10) 0.0573 (4)
N1 0.9411 (6) 0.3644 (3) 0.4379 (2) 0.0319 (7)
H1 1.143752 0.372943 0.434966 0.038*
O1 0.5273 (6) 0.4086 (3) 0.5392 (2) 0.0466 (8)

1 Source of materials

To a stirred mixture of HCO2H (0.76 g, 14 mmol, 85 %) and N-butyl-imidazolium trifluoroacetate based ionic liquids (126 mg, 0.5 mmol) was added 4′-chloro-[1,1′-biphenyl]-2-amine (2.03 g, 10 mmol) and then the reaction mixture was heated at 70 °C for 1 h. The progress of the reaction was monitored by TLC. After completion, the mixture was diluted with water (10 mL) and extracted with ether (30 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and evaporated to give residue under reduced pressure. The crude product was passed through a short pad silica-gel column (in order to remove any trace amount of ionic liquid left in the product) by elution with diethyl ether. The evaporation of the solvent under high vacuum afforded a light yellow solid. Yield: 88.4 %.

2 Experimental details

The collected diffraction data were then processed using the Bruker SAINT program [1], which applies standard corrections for absorption and decay of the X-ray source. The corrected data were then further analyzed using the SHELXT software suite to obtain the crystal structure [2]. The final refinement was performed using the Bruker Shelxl program [3], with the aid of the OLEX2 program for visualizing and refining the structure [4].

3 Comment

Formamides are a significant class of intermediates in organic syntheses, and their structures are present in a range of biologically vital compounds. The formyl group, which is essential as an amino-protecting group in peptide synthesis, has extensive applications in pharmaceutical research [5]. The structural studies of formamides derivatives have significant importance in designing and developing new materials with desired properties and applications in organic synthesis [6], [7], [8], [9].

N-(4′-chloro-[1,1′-biphenyl]-2-yl)formamide, hereafter referred to as the target compound, was synthesized and characterized through a combination of analytical methods. The two phenyl groups are non-coplanar, with a dihedral angle of 52.9°.

The crystal structure is comprised of the target molecule and layers of packing, which are primarily formed from hydrogen bonding N1–H1⋯O1. The bond length is 2.021(3) Å, and the bond angle is 139.8°. The packing is further stabilized by secondary interactions like π⃛π interactions. The result indicates that the polar C=O group is stabilized through a number of intermolecular interactions including one strong hydrogen bond between the carbonyl oxygen atom and the N-atom of an adjacent molecule. This bond forms a one-dimensional chain along a-axis direction.

Overall, the crystal structure of the target compound presented in this study provides detailed insights into the molecular organization and packing behavior. All parameters are in the typical ranges [1014].


Corresponding author: Hongjuan Tong, Xianyang Key Laboratory of Molecular Imaging and Drug Synthesis, School of Pharmacy, Shaanxi Institute of International Trade & Commerce, Xianyang, Shaanxi, China, E-mail:

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

  2. Research funding: Natural Science Foundation of Shannxi Province (2021JM-561), Scientific research plan project of Shaanxi Provincial Department of Education (22JK0277), Key Laboratory of Molecular Imaging and Drug Synthesis of Xianyang city (2021QXNL–PT-0008), Doctoral research fund project of Xianyang Vocational and Technical College (2021BK01) and the scientific research fund project of Xianyang Vocational and Technical College (2020KJB02).

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

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Received: 2023-05-21
Accepted: 2023-06-21
Published Online: 2023-07-12
Published in Print: 2023-10-26

© 2023 the author(s), published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of (N-([1,1′:4′,1″-terphenyl]-4,4′-diethyl)-2-(bis(pyridin-2-ylmethyl)amino)acetamide-κ4N,N,N″, O)tri(nitrato-kO, O′) samarium(III) - methanol - acetonitrile (1/1/1), C40H39SmN8O14
  4. The crystal structure of 6,6′-(((2-(dimethylamino)ethyl)azanediyl)bis(methylene))bis(2-chloro-4-methyl phenolate-κ4N,N,O,O′)-(pyridine-2,6-dicarboxylato-N,O,O′)-titanium(IV), C27H27Cl2N3O6Ti
  5. N′-[(1E)-(4–Fluorophenyl)methylidene]adamantane-1-carbohydrazide, C18H21FN2O
  6. Crystal structure of 4-bromo-3-nitro-1H-pyrazole-5-carboxylic acid monohydrate, C4H2N3BrO4·H2O
  7. Crystal structure of dipyridine-k1N-tris(2,2,6,6-tetramethyl-5-oxohept-3-en-3-olato-k2O,O′)dysprosium(III), DyC43H67O6N2
  8. Crystal structure of cyclo[tetraiodido-bis{μ2-1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-isopropyl-imidazol)-k2N:N}dicadmiun(II)], C26H30N10Cd2I4
  9. The crystal structure of tert-butyl (E)-3-(2-(benzylideneamino)phenyl)-1H-indole-1-carboxylate, C26H24N2O2
  10. The crystal structure of 4-(3-carboxy-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4- dihydroquinolin-7-yl)-2-methylpiperazin-1-ium 2,5-dihydroxybenzoate methanol solvate, C27H32FN3O9
  11. Crystal structure of (μ2-1-(4,4′-bipyridine-κ2N:N′)-bis[diaqua-(4-iodopyridine-2,6-dicarboxylato-κ3O,N,O′)–cobalt(II)], C24H20Co2I2N4O12
  12. The crystal structure of dimethyl 4,4′-(10,20-diphenylporphyrin-5,15-diyl)dibenzoate dichloromethane solvate, C49H36N4O4Cl2
  13. (E)-2-((E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-ylidene)hydrazine-1-carbothioamide C14H23N3S1
  14. The crystal structure of [1-(4-(trifluoromethyl)phenyl)-3,4-dihydroquinolin-2(1H)-one], C16H12F3NO
  15. Crystal structure of (E)-2-amino-N′-((3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene)benzohydrazide – dimethylformamide – water (1/1/2), C15H16N4O3·C3H7NO·2H2O
  16. Crystal structure of 3-(4-bromophenyl)-5-methyl-1H-pyrazole, C10H9BrN2
  17. Crystal structure of 1,10-phenanthrolinium bromide dihydrate, C12H9N2Br
  18. Crystal structure of N-(4′-chloro-[1,1′-biphenyl]-2-yl)formamide, C13H10ClNO
  19. The crystal structure of nitroterephthalic acid, C8H5NO6
  20. Crystal structure of (2-((4-bromo-2,6-dichlorophenyl)amino)phenyl) (morpholino)methanone, C17H15BrCl2N2O2
  21. Crystal structure of tetraaqua-bis(ethanol-κO)-tetrakis(μ2-trifluoroacetate-κ2O:O′)-bis(trifluoroacetate-κ2O)digadolinium(III) Gd2C16H20O18F18
  22. The crystal structure of dimethyl 4,4′-[10,20-bis(2,6-difluorophenyl)porphyrin-5,15-diyl]dibenzoate chloroform solvate, C50H32Cl6F4N4O4
  23. The crystal structure of N,N′-((nitroazanediyl)bis(methylene))diacetamide, C6H12O4N4
  24. The crystal structure of [bis(2,2′-bipyridine-6-carboxylato-κ3N,N,O)magnesium(II)]dihydrate, C22H18N4O6Mg
  25. Crystal structure of poly[diaqua-(bis(μ2-1,4-bis(imidazol-1-ylmethyl)benzene)-κ2N,N′] cobalt(II)-tetraqua-bis(1,4-bis(imidazol-1-ylmethyl)benzene)-κ1N)-cobalt(II) di(2,5-thiophenedicarboxylate) dihydrate, C68H76Co2N16O16S2
  26. Crystal structure of poly[chlorido-μ2-chlorido-(μ2-1-[(2-ethyl-4-methyl-1H-imidazol-1-yl)methyl]-1H-benzotriazole-κN:N’)cadmium(II)], C13H15CdN5Cl2
  27. The crystal structure of (4-hydroxybenzenesulfonate)-k1O-6,6′-((1E,1′E)- (ethane-1,2-diylbis(azaneylylidene))bis(methaneylylidene)) bis(2-methoxyphenol)-κ2N,N,μ2O,O2O, O)-(methanol)-cobalt(II) sodium(I), C25H27CoN2NaO9S
  28. Crystal structure of (1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)(4-((2-methyl-6-(trifluoromethyl)pyrimidin-4-yl)amino)piperidin-1-yl)methanone, C17H18F6N6O
  29. Crystal structure of bis{[(cyclohexylimino)(phenylimino)-l5-(methyl)diethylazane-κ2N:N′]-(ethyl)-zinc(II)]}, C38H62N6Zn2
  30. Crystal structure of 2-[(4-bromobenzyl)thio]-5-(5-bromothiophen-2-yl)-1,3,4-oxadiazole, C13H8Br2N2OS2
  31. Crystal structure of 10-methoxy-7,11b,12,13-tetrahydro-6H-pyrazino [2′,3′:5,6]pyrazino[2,1-a]isoquinoline, C15H16N4O
  32. The crystal structure of 1-propyl-2-nitro-imidazole oxide, C6H9N3O3
  33. The crystal structure of 3-nitrobenzene-1,2-dicarboxylic acid–2-ethoxybenzamide (1/1), C17H16N2O8
  34. The structure of RUB-1, (C8H16N)6[B6Si48O108], a boron containing levyne-type zeolite, occluding N-methyl-quinuclidinium in the cage-like pores
  35. The crystal structure of diaqua-(naphthalene-4,5-dicarboxylate-1,8-dicarboxylic anhydride1O)-(4′-(4-(1H-benzimidazolyl-1-yl)phenyl)-2,2′:6′,2″-terpyridine-κ3N,N′,N″)–manganese(II) dihydrate, C42H27MnN5O9·2H2O
  36. Crystal structure of 6,6′-((1E,1′E)-hydrazine-1,2-diylidenebis(methanylylidene))bis (3-(3-bromopropoxy)phenol), C20H22Br2N2O4
  37. The crystal structure of 3-(2-hydroxyphenyl)-4-phenyl-6-(p-tolyl)-2H-pyran-2-one, C24H18O3
  38. Crystal structure of bis(μ2-2-(1,5-dimethyl–3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino)methyl)phenolato-κ4O:O,N,O′)-(nitrato-κ2O,O′)dicobalt(II), C36H32Co2N8O4
  39. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α] phenanthren-3-one O-(4-fluorobenzoyl) oxime, C28H36FNO2
  40. The crystal structure of 4-aminiumbiphenyl benzenesulfonate, C18H17NO3S
  41. Synthesis and crystal structure of 1-(7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)-N,N-dimethylmethanaminiumnitrate, C18H17N3O9
  42. Crystal structure of N-(Ar)-N′-(Ar′)-formamidine, C14H12Br2N2O
  43. The crystal structure of 4-(2,4-dichlorophenyl)-2-(4-fluorophenyl)-5-methyl-1H-imidazole, C16H11Cl2FN2
  44. Crystal structure of 1-(4–chlorophenyl)-4-benzoyl-3-methyl-1H-pyrazol-5-ol, C17H13ClN2O2
  45. The crystal structure of 5-amino-1-methyl-4-nitroimidazole, C4H6O2N4
  46. Crystal structure of 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene-N,N′-bis(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-1,3,2-diazaborol-2-yl)-l2-germenediamine, C63H94B2GeN8
  47. The crystal structure of (bromido, chlorido)-tricarbonyl-(5,5′-dimethyl-2,2′-bipyridine)-rhenium(I), C15H12Br0.2Cl0.8N2O3Re1
  48. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-bis(propan-2-yl)-1H-pyrazol-4-amine, C26H36N6
  49. The crystal structure of poly[2-(4-carboxypyridin-3-yl)terephthalpoly[diaqua-(μ4-2-(6-carboxylatopyridin-3-yl)terephthalato-κ5O,N:O′:O″,O‴)]) cadmium(II)] dihydrate, C28H20Cd3N2O16
  50. Crystal structure of [tetraaqua-bis((3-carboxy-5-(pyridin-4-yl)benzoate-κ1N)cobalt(II)] tetrahydrate, C26H32CoN2O16
  51. Crystal structure of bis(μ2-azido-κ2N:N)-tetrakis(azido-κ1N)-tetrakis(1,10-phenanthroline-κ2N,N′)dibismuth(III), C48H32N26Bi2
  52. Crystal structure of (Z)-N-(4-(4-(4-((4,5,6-trimethoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)phenoxy)butoxy)phenyl)acetamide, C30H31NO8
  53. Crystal structure of poly[diaqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-bis(μ2-5-carboxybenzene-1,3-dicarboxylato-O,O′:O″)-aqua-di-zinc dihydrate solvate], C27H28N4O16Zn2
  54. Crystal structure of 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile, C12H14N2
  55. Crystal structure of chlorido-(5-nitro-2-phenylpyridine-κ2N,C)-[(methylsulfinyl)methane-κ1S]platinum(II), C13H13ClN2O3PtS
  56. The crystal structure of the co-crystal 1,4-dioxane–4,6-bis(nitroimino)-1,3,5-triazinan-2-one(2/1), C11H19N7O9
  57. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-dimethyl-1H-pyrazol-4-amine di-methanol solvate, C18H20N6·2(CH3OH)
  58. Crystal structure of catena-poly[bis(μ2-azido-k2N:N′)-(nitrato-K2N:N′)-bis(1,10-phenanthroline-K2N:N′)samarium(III)], C24H16N11O3Sm
  59. Crystal structure of (Z)-2-(4-((5-bromopentyl)oxy)benzylidene)-4,5,6-trimethoxybenzofuran-3(2H)-one, C23H25BrO6
  60. Crystal structure of bis(3,5-dimethyl-1H-pyrazol-4-ammonium) tetrafluoroterephthate, 2[C5H10N3][C8F4O4]
  61. Crystal structure of 2-amino-4-(2-fluoro-4-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  62. Crystal structure of 6-(pyridin-3-yl)-1,3,5-triazine-2,4-diamine-sebacic acid (2/1), C13H17N6O2
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