Home The crystal structure of N,N′-(Disulfanediyldi-2,1-phenylene)di(6′-methylpyridine)-2-carboxamide, C26H22N4O2S2
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The crystal structure of N,N′-(Disulfanediyldi-2,1-phenylene)di(6′-methylpyridine)-2-carboxamide, C26H22N4O2S2

  • Nana Xin , Jun Zheng and Qingpeng He EMAIL logo
Published/Copyright: July 14, 2021
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 236 Issue 5

Abstract

C26H22N4O2S2, triclinic, P 1 ‾ (no. 2), a = 7.9495(7) Å, b = 11.2494(12) Å, c = 13.7829(13) Å, α = 81.433(2)°, β = 76.536(1)°, γ = 82.641(2)°, V = 1179.7(2) Å3, Z = 2, R gt (F) = 0.0727, wRref(F2) = 0.2189, T = 298(2) K.

CCDC no.: 2092800

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: Yellow block
Size: 0.23 × 0.21 × 0.20 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.26 mm−1
Diffractometer, scan mode: Bruker SMART APEX II, φ and ω
θmax, completeness: 25.0°, 98%
N(hkl)measured, N(hkl)unique, Rint: 6008, 4109, 0.067
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2424
N(param)refined: 309
Programs: Bruker [1], SHELX [2]
Table 2:

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

Atom x y z Uiso*/Ueq
N1 0.7177 (5) 0.7664 (3) 0.2043 (3) 0.0588 (10)
H1 0.670456 0.716123 0.253320 0.071*
N2 0.6380 (6) 0.5491 (4) 0.2069 (3) 0.0718 (12)
N3 1.0316 (5) 0.7030 (3) 0.3478 (2) 0.0538 (9)
H3′ 0.997609 0.753084 0.391490 0.065*
N4 1.1458 (5) 0.9091 (3) 0.3548 (3) 0.0614 (10)
O1 0.8270 (7) 0.7863 (4) 0.0357 (3) 0.1122 (16)
O2 1.2059 (5) 0.6831 (3) 0.1943 (3) 0.0941 (13)
S1 0.54357 (15) 0.79815 (11) 0.41849 (8) 0.0582 (4)
S2 0.70671 (16) 0.71049 (10) 0.51002 (8) 0.0572 (4)
C1 0.6675 (6) 0.9025 (4) 0.3295 (3) 0.0534 (11)
C2 0.6883 (7) 1.0132 (4) 0.3573 (4) 0.0672 (13)
H2 0.643264 1.029291 0.423095 0.081*
C3 0.7743 (7) 1.0987 (5) 0.2886 (4) 0.0756 (15)
H3 0.785486 1.172740 0.307529 0.091*
C4 0.8438 (7) 1.0744 (5) 0.1919 (4) 0.0714 (14)
H4 0.902745 1.132176 0.145583 0.086*
C5 0.8274 (6) 0.9656 (4) 0.1626 (3) 0.0609 (12)
H5 0.875053 0.950463 0.096787 0.073*
C6 0.7399 (6) 0.8781 (4) 0.2308 (3) 0.0510 (11)
C7 0.7597 (7) 0.7257 (5) 0.1128 (4) 0.0683 (13)
C8 0.7114 (7) 0.6009 (4) 0.1161 (4) 0.0624 (12)
C9 0.7419 (7) 0.5429 (5) 0.0286 (4) 0.0732 (14)
C10 0.6893 (9) 0.4266 (6) 0.0439 (5) 0.0928 (19)
H10 0.706046 0.384018 −0.011033 0.111*
C11 0.6149 (9) 0.3740 (6) 0.1356 (6) 0.097 (2)
H11 0.580265 0.296503 0.144218 0.116*
C12 0.5915 (8) 0.4382 (5) 0.2167 (4) 0.0835 (16)
H12 0.541239 0.402251 0.280347 0.100*
C13 0.8273 (10) 0.5978 (6) −0.0750 (4) 0.110 (2)
H13A 0.831778 0.542691 −0.122594 0.165*
H13B 0.943163 0.613764 −0.075150 0.165*
H13C 0.761290 0.672054 −0.093152 0.165*
C14 0.8085 (6) 0.5824 (4) 0.4495 (3) 0.0490 (10)
C15 0.7402 (6) 0.4719 (4) 0.4800 (3) 0.0575 (12)
H15 0.641084 0.465493 0.531268 0.069*
C16 0.8191 (7) 0.3712 (4) 0.4345 (4) 0.0629 (12)
H16 0.775195 0.296642 0.455838 0.076*
C17 0.9627 (6) 0.3826 (4) 0.3576 (4) 0.0611 (12)
H17 1.012461 0.315849 0.324980 0.073*
C18 1.0348 (6) 0.4901 (4) 0.3277 (3) 0.0559 (11)
H18 1.134389 0.494795 0.276634 0.067*
C19 0.9592 (6) 0.5924 (4) 0.3734 (3) 0.0493 (10)
C20 1.1469 (6) 0.7423 (4) 0.2644 (3) 0.0559 (11)
C21 1.1947 (6) 0.8672 (4) 0.2649 (3) 0.0527 (11)
C22 1.2820 (6) 0.9350 (4) 0.1781 (3) 0.0579 (12)
C23 1.3214 (6) 1.0475 (5) 0.1901 (4) 0.0724 (14)
H23 1.379576 1.095328 0.134613 0.087*
C24 1.2765 (7) 1.0902 (4) 0.2820 (4) 0.0715 (14)
H24 1.305139 1.165410 0.289570 0.086*
C25 1.1884 (7) 1.0185 (4) 0.3621 (4) 0.0673 (13)
H25 1.156608 1.047116 0.424353 0.081*
C26 1.3245 (8) 0.8923 (5) 0.0747 (4) 0.0847 (17)
H26A 1.414779 0.826687 0.072271 0.127*
H26B 1.362995 0.957700 0.024447 0.127*
H26C 1.222498 0.865556 0.062098 0.127*

Source of material

In the typical case, 6-methyl-2-pyridinecarboxylic acid (1.2 mmol), N-methyl morpholine (0.4 mmol), and ethylchloroformate (0.4 mmol) were successively added to the 10 mL dry tetrahydrofuran (THF) and stirred at −15 °C for 20 min. After 20 min of stirring, 2-(2-(2-aminophenyl)disulfanyl)-benzenamine (0.3 mmol) was added to the solution, and the reaction mixture was stirred for 2 h at −15 °C. The stirring was later continued at room temperature for an additional 12 h. The reaction was monitored by using thin layer chromatography. After the reaction was completed, the reaction mixture was concentrated to remove the THF and then extracted into ethyl acetate. The organic layer was dried over sodium sulfate and was concentrated under vacuum, to get crude solid, which was recrystallized from chloroform-acetonitrile to get diffraction-quality crystals. Yield 72%. Anal. Calc. for C26H22N4O2S2: C, 64.18; H, 4.56; N, 11.51; S, 13.18; found: C, 64.37; H 4.32; N 11.48; S, 13.15.

Experimental details

Hydrogen atoms were assigned with common isotropic displacement factors Uiso (H) = 1.2 times Ueq (C, benzene ring; N, amide) and Uiso(H) = 1.5 times Ueq(C, methyl carbon). All the H atoms were refined as riding on their parent atom.

Comment

In nature, disulfide compounds have received much attention in the field of coordination chemistry, pharmaceutical chemistry, biochemistry, and organic synthesis [3], [4], [5]. It is particularly noteworthy that the disulfide bonds played an important role in the areas of folding, structure, and stability of the proteins because the S–S bonds are the only readily reversible covalent chemical cross-linking bonds presented in the native proteins [6], [7]. Consequently, the syntheses of new disulfide compounds has become a hot spot. For instance, Sobczak et al. firstly described that the heterodimeric product 1-[(4-chloro-phenyl)disulfanyl]-2-nitrobenzene was synthesized by the reaction of bis 4-chlorophenyl disulfide [(4–ClPhS)2]and bis 2-nitrophenyl disulfide [(2–NO2PhS)2] [8]. Singh’s group synthesized three hexadentate disulfide ligands and tested their performance for binding with library of metal ions [9]. So far, despite some thrilling work has been achieved, newly designed disulfide compounds are long-sought-after yet still unmet.

The molecular structure of the title disulfide compound is shown in the figure. Single crystal X-ray diffraction analysis reveals that the title structure consists of one diphenyl disulfide unit and two (6′-methylpyridine)-2-carboxamide units, in two halves of the molecule (about S–S bond) the phenyl ring and the substituted pyridine are forming very different dihedral angles (31.91(2); 6.60(2)°) between the phenyl plane (C14/C15/C16/C17/C18/C19) and the pyridine plane (C21/C22/C23/C24/C25/N4) and the phenyl plane (C1/C2/C3/C4/C5/C6) and the pyridine plane (C8/C9/C10/C11/C12/N2), respectively, suggesting that one-half is relatively more planar than the other. The torsion angle C1–S1–S2–C14 is 90.32° in the molecular structure of the title compound and shows a kink around the S–S bond making the two halves out of plane with each other. The bond distance of S–S is 2.0758(17) Å, which is similar with that of the reported N,N′-(disulfanediyl-bis(4-(morpholin-4-yl)-2,1-phenylene)) bis(1,3-benzothiazol-2-amine) chloroform solvate [10]. Additionally, the title compound adopts weak π⃛π interactions between the pyridine ring (C21/C22/C23/C24/C25/N4) and phenyl ring (C1/C2/C3/C4/C5/C6) with a centroid to centroid distance as 3.83 Å, which was similar to that of the reported N,N′-(disulfanediyldi-2,1-phenylene)dipyridine-2-carboxamide [11].

Corresponding author: Qingpeng He, School of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252000, Shandong, China, E-mail:

Funding source: Liaocheng University Doctoral Foundation

Award Identifier / Grant number: 318051437

  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 funded by Liaocheng University Doctoral Foundation (318051437).

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

References

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Received: 2021-05-24
Accepted: 2021-06-28
Published Online: 2021-07-14
Published in Print: 2021-09-27

© 2021 Nana Xin et al., published by De Gruyter, Berlin/Boston

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

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  68. The crystal structure of 3-(carboxymethyl)-1-ethenyl-1H-imidazol-3-ium chloride, C7H9N2O2Cl
  69. The crystal structure of adamantylmethoxydiphenylsilane, C23H28OSi
  70. Redetermination of the crystal structure of (2E,4Z,13E,15Z)-3,5,14,16-tetramethyl-2,6,13,17-tetraazatricyclo[16.4.0.07,12]docosa-1(22),2,4,7,9,11,13,15,18,20-decaene, C22H24N4
  71. Crystal structure of (E)-7-hydroxy-2-((6-methoxypyridin-2-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H15NO3
  72. Crystal structure of catena-poly[diaqua-bis(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2 N:N′)cobalt(II)] dinitrate, C18H28N10O8Co
https://doi.org/10.1515/ncrs-2021-0206
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of [aqua-(4-iodopyridine-2,6-dicarboxylato-κ3 O,N,O′)-(1,10-phenanothroline-κ2 N,N′)copper(II)] dihydrate, C19H16O7N3CuI
  4. The crystal structure of tetrakis(1-isopropyl-1H-imidazolium) octamolybdate, C24H44Mo8N8O26
  5. Crystal structure of catena-poly[bis(µ2-3,5-bis(1-imidazolyl)pyridine-κ2 N:N′)-(µ2-3-nitrophthalato-k3 O,O′:O″)cadmium(II)] dihydrate, C30H25N11O8Cd
  6. The crystal structure of diaqua-bis(2-(3-(1H-pyrazol-4-yl)-1H-1,2,4-triazol-5-yl)pyridine-κ2 N:N′)-bis(3,5-dicarboxybenzoato-κ1 O)cobalt(II), C38H30CoN12O14
  7. Crystal structure of the nickel(II) complex aqua-(2,6-di(pyrazin-2-yl)-4,4′-bipyridine-κ3 N,N′,N′′)-(phthalato-κ2 O,O′)nickel(II) tetrahydrate, C26H26N6O9Ni
  8. The crystal structure of 1-[5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)-1H-pyrrol-3-yl]-N-methylmethanaminium 3-carboxyprop-2-enoate, C21H20FN3O6S
  9. The crystal structure of 1,2-bis(4-pyridyl)ethane - 4,4-dihydroxydiphenylmethane (1/1), C25H21N2O2
  10. Crystal structure of bis(2-((E)-5-chloro-2-hydroxybenzylidene)hydrazineyl)methaniminium trifluoroacetate dihydrate, C34H36Cl4N10O12
  11. Crystal structure of 1-cyclopropyl-7-ethoxy-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, C15H13F2NO4
  12. Crystal structure of methyl 3-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)benzoate, C18H15BN2O2
  13. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-2-hydroxybenzohydrazide, C14H11ClN2O3
  14. Crystal structure of Al-rich fluorophlogopite, K1.0(Mg2.8Al0.2)(Si2.8Al1.2)O10F2
  15. The crystal structure of 4,5-diiodo-1,3-dimesityl-1H-1,2,3-triazol-3-ium hexafluoridoantimonate(V), C20H22F6I2N3Sb
  16. Crystal structure of tris(3-iodopyridin-1-ium) catena-poly[(hexachlorido-κ1 Cl)-(μ2-trichlorido-κ2 Cl:Cl)diantimony(III)], C15H15Cl9I3N3Sb2
  17. Crystal structure of methyl 2-(1H-naphtho[1,8-de][1.3.2]diazaborinin-2(3H-yl)benzoate C18H15BN2O2
  18. The crystal structure of 1,8-bis(4-methoxybenzoyl)naphthalene-2,7-diyl dibenzoate, C40H28O8
  19. Crystal structure of 2-bromo-1,3,6,8-tetramethylBOPHY (BOPHY = bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine), C14H15B2BrF4N4
  20. The crystal structure of (E)-3-chloro-2-(2-(2-fluorobenzylidene)hydrazinyl)pyridine, C12H9ClFN3
  21. Crystal structure of bis(µ2- 4-iodopyridine-2,6-dicarboxylato-κ3O:N:O′)-bis(4-iodopyridine-2,6-dicarboxylato-κ3O:N:O′)-bis(µ2-1-(4-pyridyl)piperazine-κ2N:N′)-hexa-aqua-tetra-copper(II), C46H46Cu4I4N10O22
  22. Crystal structure of poly[diaqua-(μ2-2,5-dihydroxyterephthalato-κ2O:O′)(μ2-bis(4-pyridylformyl)piperazine-κ2N:N′)cadmium(II)] dihydrate, C24H28CdN4O12
  23. Crystal structure of poly[aqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-(μ3-2,3,5,6-tetrafluoroterephthalato-κ3O:O′:O′′)cadmium(II)], C17H14N4O5F4Cd
  24. Crystal structure of 6-(quinolin-8-yl)benzo[a]phenanthridin-5(6H)-one, C26H16N2O
  25. The crystal structure of aqua-bis(6-chloropicolinato-κ2N,O)copper(II), C12H8Cl2N2O5Cu
  26. Crystal structure of catena-poly[diaqua-bis(μ2-4,4′-bipyridyl-κ2N:N′) disilver(I)] 4-oxidopyridine-3-sulfonate trihydrate, C25H29Ag2N5O9S
  27. The crystal structure of 4-(3-bromophenyl)pyrimidin-2-amine, C10H8BrN3
  28. Crystal structure of 6-oxo-4-phenyl-1-propyl-1,6-dihydropyridine-3-carbonitrile, C15H14N2O
  29. Crystal structure of 4-(2,2-difluoroethyl)-2,4-dimethyl-6-(trifluoromethyl)isoquinoline-1,3(2H,4H)-dione, C14H12F5NO2
  30. Crystal structure of dibromido-(1-methyl-1H-imidazole-κ1N)-(3-(3-methyl-1H-imidazol-3-ium-1-yl)propanoato-κ1O)zinc(II), C11H16Br2N4O2Zn
  31. The crystal structure of 1,1′-(((2 (dimethylamino)ethyl)azanediyl)bis(methylene)) bis(naphthalen-2-olato-κ4 N,N′,O,O′)-(pyridine-2,6-dicarboxylato-N,O,O′)- titanium(IV) ─ dichloromethane (2/1), C33H29N3O6Ti
  32. The layered crystal structure of bis(theophyllinium) hexachloridostannate (IV), C14H18N8O8SnCl6
  33. The crystal structre of 3-(1-ethenyl-1H-imidazol-3-ium-3-yl)propane-1-sulfonate, C8H12N2O3S
  34. Synthesis and crystal structure of di-tert-butyl 1″-acetyl-2,2″,9′-trioxo-4a′,9a′-dihydro-1′H,3′H,9′H-dispiro[indoline-3,2′-xanthene-4′,3″-indoline]-1,3′-dicarboxylate, C39H38N2O9
  35. The crystal structure of 4-chloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H9ClN2O2
  36. The crystal structure of 1-fluoro-4-(p-tolylethynyl)benzene, C15H11F
  37. The crystal structure of bis[4-bromo-2-(1H-pyrazol-3-yl) phenolato-κ2N,O] copper(II), C18H12Br2CuN4O2
  38. The crystal structure of poly[(μ 3-imidazolato-κ 3 N:N:N′)(tetrahydrofuran- κ 1 O)lithium(I)], C7H11LiN2O
  39. Crystal structure of N′,N′′′-((1E,1′E)-(propane-2,2-diylbis(1H-pyrrole-5,2diyl))bis(methaneylylidene))di(nicotinohydrazide) pentahydrate, C25H24N8O2·5H2O
  40. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-ethyl-1H-imidazol-3-ium hexafluoridophos-phate(V), C9H15F6N2O2P
  41. Crystal structure of (1,10-phenanthroline-κ2N,N′)-bis(3-thiophenecarboxylato-κ2O,O′)copper(II), C22H14N2O4S2Cu
  42. The crystal structure of 2-amino-3-carboxypyridin-1-ium iodide hemihydrate, C6H8IN2O2.5
  43. Crystal structure of (E)-7-methoxy-2-((6-methoxypyridin-2-yl)methylene)-tetralone, C18H17NO3
  44. The crystal structure of [μ-hydroxido-bis[(5,5′-dimethyl-2,2′-bipyridine-κ2N,N′)-tricarbonylrhenium(I)] bromide hemihydrate, C30H26N4O9Re2Br
  45. The crystal structure of 2,5-bis(3,5-dimethylphenyl)thiazolo[5,4-d]thiazole, C20H18N2S2
  46. The crystal structure of 5-benzoyl-1-[(E)-(4-fluorobenzylidene)amino]-4-phenylpyrimidin-2(1H)-one, C24H16FN3O2
  47. Crystal structure of monocarbonyl(N-nitroso-N-oxido-phenylamine-κ 2 O,O′)(tricyclohexylphosphine-κP)rhodium(I), C25H39N2O3PRh
  48. Crystal structure of poly[bis[μ3-1,3,5-tris[(1H-imidazol-1-yl)methyl]benzene-κ3N:N′:N″]nickel(II)] hexafluorosilicate, C36H36N12NiSiF6
  49. The crystal structure of 13-(pyrazole-1-yl-4-carbonitrile)-matrine, C19H25N5O
  50. Crystal structure of 3,5-bis((E)-4-methoxy-2-(trifluoromethyl)benzylidene)-1-methylpiperidin-4-one, C24H21F6NO3
  51. The crystal structure of N,N′-(Disulfanediyldi-2,1-phenylene)di(6′-methylpyridine)-2-carboxamide, C26H22N4O2S2
  52. Crystal structure of (E)-7-fluoro-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  53. Crystal structure of ethyl 1-(4-fluorophenyl)-4-phenyl-1H-pyrrole-3-carboxylate, C19H16FNO2
  54. The crystal structure of cis-diaqua-bis (N-butyl-N-(pyridin-2-yl)pyridin-2-amine-κ2N,N′)cobalt(II)] dichloride trihydrate, C28H44Cl2N6O5Co
  55. Crystal structure of (E)-7-methoxy-2-((6-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C18H17NO3
  56. Crystal structure of (E)-2-((3-fluoropyridin-4-yl)methylene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  57. The crystal structure of 6-bromohexanoic acid, C6H11BrO2
  58. The crystal structure of 4-chloro-thiophenol, C6H5ClS
  59. The crystal structure of 4-bromobenzyl chloride, C7H6BrCl
  60. The crystal structure of di-tert-butyl dicarbonate, C10H18O5
  61. The crystal structure of (2-(4-chlorophenyl)-5-methyl-1,3-dioxan-5-yl)methanol, C12H15ClO3
  62. The crystal structure of the co-crystal: 2-hydroxybenzoic acid – N′-(butan-2-ylidene)pyridine-4-carbohydrazide, C10H13N3O·C7H6O3
  63. Crystal structure and anti-inflammatory activity of (E)-7-fluoro-2-((5-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  64. Crystal structure of (E)-7-fluoro-2-((6-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  65. Crystal structure of 1,1′-(butane-1,4-diyl)bis(3-propyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C32H56F24N8P4
  66. The crystal structure of dichlorido-bis(3-methyl-3-imidazolium-1-ylpropionato-κ2)-cadmium(II), C14H20CdCl2N4O4
  67. Crystal structure of 1-(2-cyanobenzyl)-3-cyano-4-phenyl-4-(2-cyanobenzyl)-1,4-dihydropyridine monohydrate, C56H42N8O
  68. The crystal structure of 3-(carboxymethyl)-1-ethenyl-1H-imidazol-3-ium chloride, C7H9N2O2Cl
  69. The crystal structure of adamantylmethoxydiphenylsilane, C23H28OSi
  70. Redetermination of the crystal structure of (2E,4Z,13E,15Z)-3,5,14,16-tetramethyl-2,6,13,17-tetraazatricyclo[16.4.0.07,12]docosa-1(22),2,4,7,9,11,13,15,18,20-decaene, C22H24N4
  71. Crystal structure of (E)-7-hydroxy-2-((6-methoxypyridin-2-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H15NO3
  72. Crystal structure of catena-poly[diaqua-bis(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2 N:N′)cobalt(II)] dinitrate, C18H28N10O8Co
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