Startseite Crystal structure of 2-(4-bromophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16BrIN2
Artikel Open Access

Crystal structure of 2-(4-bromophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16BrIN2

  • Long-Sheng Zou EMAIL logo und Xian-You Yuan
Veröffentlicht/Copyright: 17. Oktober 2018

Abstract

C19H16BrIN2, monoclinic, P21/c (no. 14), a = 7.3409(17) Å, b = 18.494(4) Å, c = 12.905(3) Å, β = 93.372(3)°, V = 1749.0(7) Å3, Z = 4, Rgt(F) = 0.0205, wRref(F2) = 0.0512, T = 296(2) K.

CCDC no.: 1871996

The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Block
Size:0.38 × 0.34 × 0.30 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:4.12 mm−1
Diffractometer, scan mode:Bruker SMART, φ and ω-scans
θmax, completeness:26.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:18407, 3616, 0.018
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3262
N(param)refined:210
Programs:Bruker programs [1], SHELX [2], [3]
Table 2:

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

AtomxyzUiso*/Ueq
I10.84550(2)0.18172(2)0.13134(2)0.04970(6)
Br10.22252(4)0.48680(2)0.41402(2)0.05925(8)
N10.3063(2)0.12110(10)0.33821(13)0.0393(4)
C10.2763(3)0.00601(11)0.42360(17)0.0384(4)
N20.2413(2)0.11962(9)0.51234(13)0.0370(4)
C20.3030(3)0.04431(12)0.33151(16)0.0404(5)
C30.3262(4)0.00870(15)0.2400(2)0.0585(6)
H30.3412540.0344140.1791900.070*
C40.3269(4)−0.06717(16)0.2397(2)0.0682(8)
H40.343311−0.0913850.1777850.082*
C50.3045(3)−0.10600(14)0.3264(3)0.0627(7)
H50.306707−0.1562360.3235280.075*
C60.2775(3)−0.07069(12)0.4223(2)0.0475(5)
C70.2479(3)−0.10779(14)0.5153(2)0.0585(7)
H70.245956−0.1580660.5157960.070*
C80.2222(4)−0.07086(15)0.6040(2)0.0604(7)
H80.204279−0.0963650.6646230.072*
C90.2222(3)0.00526(14)0.60629(19)0.0509(5)
H90.2053700.0297810.6679160.061*
C100.2471(3)0.04273(11)0.51670(16)0.0368(4)
C110.1932(3)0.15803(13)0.60708(18)0.0492(5)
H11A0.2926740.1547090.6585660.074*
H11B0.0862790.1364390.6333630.074*
H11C0.1692510.2079320.5909760.074*
C120.2706(3)0.15538(11)0.42504(15)0.0358(4)
C130.3585(4)0.16118(14)0.24536(19)0.0542(6)
H13A0.2614430.1583280.1923150.081*
H13B0.4672010.1403380.2201830.081*
H13C0.3807380.2109090.2633120.081*
C140.2615(3)0.23594(11)0.42463(16)0.0393(4)
C150.1098(3)0.26924(13)0.37634(18)0.0478(5)
H150.0158160.2415780.3453380.057*
C160.0995(3)0.34381(13)0.37474(19)0.0493(5)
H16−0.0023940.3665690.3434020.059*
C170.2400(3)0.38436(12)0.41947(17)0.0439(5)
C180.3919(3)0.35184(13)0.46772(18)0.0483(5)
H180.4862080.3797420.4977960.058*
C190.4014(3)0.27727(13)0.47059(18)0.0476(5)
H190.5021140.2547050.5035270.057*

Source of material

Iodomethane (3.02 g, 0.021 mol) was added dropwise to a solution of 2-(4-bromophenyl)-1-methyl-1H-perimidine (3.37 g, 0.01 mol) in dimethylformamide (20 mL) at 373 K. The mixture was heated for 8 h, giving a yellow precipitate. After cooling, the yellow solid was filtered, washed with anhydrous ethanol and dried under vacuum to give the desired salt 2-(4-bromophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide (3.35 g, 70%). Light yellow needle crystals were obtained by recrystallized from anhydrous ethanol.

Experimental details

All hydrogen atoms were identified in difference Fourier syntheses. The methyl groups were idealized and refined using rigid groups allowed to rotate about the N—C bond (AFIX 137 option of the SHELXL program). The Uiso values of the hydrogen atoms of methyl groups were set to 1.5Ueq(C) and those of all other hydrogen atoms were set to 1.2Ueq(C).

Discussion

Perimidines have drawn extensive examinations for a long time, because they exhibit a diverse range of biological activities [4], [5], [6]. There are several preparative methods for the synthesis of perimidine derivatives [7], [8], [9], [10], [11], [12]. And some structures are already reported [7], [8], [10]. Herein, a novel perimidine compound was synthesized and characterized by single-crystal X-ray diffraction.

In the title structure, the bond angles of N(1)—C(12)—N(2), N(1)—C(12)—C(14) and N(2)—C(12)—C(14) are 121.72(19), 119.03(18) and 119.25(18) in turn, which indicates the sp2 hybridization state of C12 and the new-formed heterocyclic ring is almost planar. Geometric parameters are in perfect accord with those in similar structure [7], [8], [10].

Acknowledgements

This work was financially supported by the Research Foundation for PhD of Guilin University of Aerospace Technology.

References

1. Bruker: APEX3, SAINT-Plus, XPREP. Bruker AXS Inc., Madison, WI, USA (2016).Suche in Google Scholar

2. Sheldrick, G. M.: SHELXT – Integrated space-group and crystal-structure determination. Acta Crystallogr. A71 (2015) 3–8.10.1107/S2053273314026370Suche in Google Scholar

3. Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Suche in Google Scholar

4. Bu, X.; Deady, L. W.; Finlay, G. J.; Baguley, B. C.; Denny, W. A.: Synthesis and cytotoxic activity of 7-oxo-7H-dibenz[f,ij]isoquinoline and 7-oxo-7H-benzo[e]perimidine derivatives. J. Med. Chem. 44 (2001) 2004–2014.10.1021/jm010041lSuche in Google Scholar

5. Farghaly, T. A.; Mahmoud, H. K.: Synthesis, zautomeric structures, and antitumor activity of new perimidines. Arch. Pharm. 346 (2013) 392–402.10.1002/ardp.201200486Suche in Google Scholar

6. Fu, C. R.; Pei, J.; Ning, Y.; Liu, M.; Shan, P. C.; Liu, J.; Li, Y. Q.; Hu, F. Z.; Zhu, Y. Q.; Yang, H. Z.; Zou, X. M.: Synthesis and insecticidal activities of novel pyrazole oxime ether derivatives with different substituted pyridyl rings. Pest Manag. Sci. 70 (2013) 1207–C1214.10.1002/ps.3672Suche in Google Scholar

7. Yuan, L.; Li, Z. Y.; Yuan, X. Y.; Zhang, M.; Liu, F.: Crystal structure of 1,3-dimethyl-2-phenyl-1H-perimidin-3-ium iodide, C19H17IN2. Z. Kristallogr. NCS. 232 (2017) 541–543.10.1515/ncrs-2016-0302Suche in Google Scholar

8. Zhang, M.; Yuan, L.; Yuan, X. Y.; Li, Z. Y.: Crystal structure of 4-(1,3-dimethyl-2,3-dihydro-1H-perimidin-2-yl)benzonitrile, C20H17N3. Z. Kristallogr. NCS. 232 (2017) 267–268.10.1515/ncrs-2016-0233Suche in Google Scholar

9. Hendrickson, J. B.; Hussoin, M. S.: Seeking the ideal dehydrating reagent. J. Org. Chem. 52 (1987) 4137–4139.10.1021/jo00227a041Suche in Google Scholar

10. Li, Z. Y.; Yuan, L.; Yuan, X. Y.; Zhang, M.: Crystal structure of 2-(4-chlorophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16ClIN2. Z. Kristallogr. NCS. 232 (2017) 821–822.10.1515/ncrs-2017-0062Suche in Google Scholar

11. Vanden, E. J. J.; Delfosse, F.; Mayence, A.; Haverbeke, Y. V.: Old reagents, new results-aromatization of hantzsch 1,4-dihydropyridines with manganese-dioxide and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Tetrahedron 51 (1995) 5813–5818.10.1016/0040-4020(95)00318-3Suche in Google Scholar

12. Deady, L. W.; Rodemann, T. J.: Synthesis of perimidine and fused perimidine derivatives from reaction of 1,8-naphthalenediamine with an iminoisocoumarin. Heterocycl. Chem. 35 (1998) 1417–1419.10.1002/jhet.5570350633Suche in Google Scholar

Received: 2018-08-09
Accepted: 2018-10-08
Published Online: 2018-10-17
Published in Print: 2018-12-19

©2018 Long-Sheng Zou et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure of bis(6,6′-((ethane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2,4-diiodophenolato)-κ4N,N′,O,O′)cer(IV), C32H20CeI8N4O4
  3. Crystal structure of (6,6′-((ethane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2-chlorophenolato-κ2N,O))copper(II), C16H12Cl2CuN2O2
  4. Crystal structure of poly[aqua-(μ3-4-(pyridin-4-yl)isophthalato-κ4O,O′:O′′:O′′′)-(μ2-5-carboxy-2-(pyridin-4-yl)benzoato-κ2O:O′)samarium(III)], C26H18N2O9Sm
  5. Crystal structure of 1-{4-[(2-hydroxy-5-nitrobenzylidene)amino]phenyl}ethanone O-methyl oxime, C16H15N3O4
  6. Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)-bis(μ2-1-(8-(2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)naphthalen-2-olato-κ6O:O,N,N′,O′:O′)trizinc(II), C44H38Zn3N4O12
  7. Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)–bis(μ2–(8-(2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)naphthalen-2-olato-κ6O:O,N,N′,O′:O′)tricobalt(II), C44H38Co3N4O12
  8. Crystal structure of poly[aqua(μ4-2,2′,2′′-nitrilotriacetato-κ6O1,O3,O5:O2:O4:O6)-yttrium(III)], C6H8NO7Y
  9. Crystal structure of catena-poly[bromido-(μ2-pyrazine-2-carboxylato-κ3N:N′,O)copper(II)], C10H6N4Cu2O4Br
  10. Crystal structure of poly[dodekais(μ2-2,6-difluorobenzoato-κ2O:O′)-bis((μ3-hexamethylenetetramine-κ3N:N′:N′′)hexacopper(II)], C48H30N4O12F12Cu3
  11. Crystal structure of methyl 4-(4-hydroxy-3-nitrophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C18H18N2O6
  12. Crystal structure of N-phenyl-2-(propan-2-ylidene)hydrazine-1-carbothioamide, C10H13N3S
  13. Crystal structure of sodium caesium zinc phosphate, NaCsZnP2O7
  14. Crystal structure of methyl 4-(4-isopropylphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylate, C23H29NO3
  15. Crystal structure of catena-poly[bis(μ2-1,3-di(4H-1,2,4-triazol-4-yl)benzene-κ2N:N′)-bis(thiocyanato-κ1N)cobalt(II), C22H16CoN14S2
  16. Crystal structure of catena-poly[(μ2-2,5-di(pyridin-3-yl)-1,3,4-thiadiazole-κ2N:N′)-bis(2,5-di(pyridin-3-yl)-1,3,4-thiadiazole-κ1N)-bis(thiocyanato-κ1N)cobalt(II)], C38H24CoN14S5
  17. Crystal structure of bis(2,5-di(pyridin-2-yl)-1,3,4-thiadiazole-κ2N,N′)-bis(thiocyanato-κ1N)cobalt(II), C26H16CoN10S4
  18. Crystal structure of (bis((1H-benzo[d]imidazol2-yl)methyl)amine-κ3N,N′,N′′)-(pyridine-2,6-dicarboxylato-κ3N,O,O′)zinc(II) — methanol — water (1/2/1), C25H28N6O7Zn
  19. Crystal structure of catena-poly[triaqua-(μ2-5-methoxy-isophthalato-κ2O:O′)copper(II)], C9H12CuO8
  20. Structure and photochromism of 1-[2-methyl-5-phenyl-3-thienyl]-2-[2-methyl-5-(4-chlorophenyl)-3-thienyl]3,3,4,4,5,5-hexafluorocyclopent-1-ene, C27H16ClF6S2
  21. Crystal structure of methyl 4-(3-phenoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C26H27NO4
  22. Crystal structure of poly[diaqua-di-μ2-hydroxido-(μ4-3,4,5,6-tetrafluoro-1,2-phthalato-κ4O:O′:O′′:O′′′)-(μ4-3,4,5,6-tetrafluoro-1,2-phthalato-κ5O,O:O′:O′′:O′′′)disamarium(III)] – bipyridine (2/1), C21H11NF16O12Sm2
  23. Crystal structural of diethyl 4-(3,5-dibromo-4-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, C19H21Br2NO5
  24. Crystal structure of catena-poly[tetraaqua(μ2-4-(1H-imidazol-1-yl)pyridine-κ2N:N′))zinc(II)] thiophene-2,5-dicarboxylate, C14H17N3O8ZnS
  25. Crystal structure of (20S)-20-(dimethylamino)-3-(tigloylamino)-5α-pregn-2,16-dien-4-one, C28H42N2O2
  26. Crystal structure of rac-trans-N,N′-bis(3,5-diiodosalicylidene)-1,2-cyclohexanediamine, C20H18I4N2O2
  27. Crystal structure of 2-bromo-7-(4-(dimethylamino)phenyl)-10-methylacridin-9 (10H)-one, C22H19BrN2O
  28. Crystal structure of catena-poly[(μ2-pentane-1,5-dicarboxylato-κ2O:O′)-(μ2-2-[(1H-imidazol-1-yl)methyl]-6-methyl-1H-benzimidazole-κ2N:N′)zinc(II)] sesquihydrate, C17H21N4O5.5Zn
  29. Crystal structure of ethyl 2-amino-4-(3,4-difluorophenyl)-5-oxo-4H,5H-pyrano[3,2-c] chromene-3-carboxylate, C21H15F2NO5
  30. Crystal structure of 9-(5-methylthiophen-2-yl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione, C18H18O3S
  31. Crystal structure of [5,5′-((propane-1,3-diylbis(azanylylidene))bis(ethan-1-yl-2-ylidene))bis(3-(ethoxycarbonyl)-2,4-dimethylpyrrol-1-ido)-κ4N,N′,N′′,N′′′]nickel(II), C23H30N4O4Ni
  32. Crystal structure of (Z)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazineyl) terephthalic acid-dimethylsulfoxide (1/1), C18H15N3O6 ⋅ C2H6OS
  33. Crystal structure of (2E,4Z)-dimethyl 4-((phenylamino)methylene)pent-2-enedioate, C14H15N1O4
  34. Crystal structure of (2Z,2′Z)-1,1′-(pyridine-2,6-diyl) bis(3-hydroxy-3-phenylprop-2-en-1-one), C23H17NO4
  35. Crystal structure of ethyl 2-amino-4-(3-bromophenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carboxylate, C21H16BrNO5
  36. Crystal structure of bis(μ2-3,5-dichloro-2-oxidobenzoato-κ4O,O′:O′,O′′)-hexakis(μ2-pivalato-κ2O:O′)-bis(pivalato-κ2O,O′)-tetrakis(1,10-phenanthroline-κ2N,N′)tetragadolinium(III), C102H108Cl4Gd4N8O22
  37. Crystal structure of catena-poly[aqua-bis(formato-κ1O)-(μ2-1,1′-(oxybis(1,4-phenylene))-bis(1H-1,2,4-triazole)-κ2N:N′)copper(II)]hydrate, C18H16CuN6O6
  38. Crystal structure of 5-bromo-2-(naphthalen-6-yl)pyridine, C15H10BrN
  39. Crystal structure of N-(4-methoxybenzyl)pyridazin-3-amine- a rare Z′ = 4 structure, C12H13N3O
  40. Crystal structure of bis(perchlorato-κ1O)-bis(3,4,5-trimethoxy-N-(pyridin-2-yl)benzamide-κ2N,O)copper(II), C32H30Cl2CuN4O16
  41. Crystal structure of methyl 4-methyl-2,5-di(pyridin-4-yl)-1H-pyrrole-3-carboxylate monohydrate C17H15N3O2⋅H2O
  42. Crystal structure of dimethyl 5-(10-(methoxycarbonyl)anthracen-9-yl) isophthalate,C26H20O6
  43. Crystal structure of tert-butyl (R)-(1-(benzylamino)-3-methoxy-1-oxopropan-2-yl)carbamate, C16H24N2O4
  44. Crystal structure of aqua-bis(1,5-dimethyl-2-phenyl-4-(((E)-4-pyridylmethylene)amino)pyrazolidin-3-one-κN)-(nitrato-κO)-(nitrato-κ2O,O′)zinc(II), C34H34N10O9Zn
  45. Crystal structure of catena-poly[dichlorido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O)cobalt(II)] – methanol (1/1), C18H20Cl2CoN4O2
  46. Crystal structure of poly[diaqua-bis(μ2-1-(4-(1H-imidazol-1-yl)benzyl)-1H-1,2,4-triazole-κ2N:N′)manganese(II)]bis(2-carboxybenzoate) dihydrate, MnC40H40N10O12
  47. The crystal structure of 4-((3,4-dichlorobenzylidene)amino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one, C18H15Cl2N3O
  48. Crystal structure of bis(2-methoxy-6-((2-(pyrimidin-2-yl)hydrazono)methyl)phenolato-κ3N,N′,O)iron(III) perchlorate, C24H22N8O8ClFe
  49. The crystal structure of 2-[4-hydroxy-3-methoxyphenyl]-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl, C14H19N2O4
  50. Crystal structure of diaqua-bis(3,3-dimethylacrylato-κ2O,O′)zinc(II), C10H18ZnO6
  51. Crystal structure of dichloro-tetrakis[(E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol-κN]cadmium (II), C60H74CdCl6N12O4
  52. Crystal structure of (20R)-20,25-epoxy-dammaran-3,12-dione, C30H48O3
  53. Crystal structure of (E)-3′,6′-bis(ethylamino)-2′,7′-dimethyl-2-((pyridin-2-ylmethylene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C32H31N5O2
  54. The crystal structure of 2-(4-fluorophenyl)-1,3,4-oxadiazole, C8H5FN2O
  55. Crystal structure of (2,2′-bipyridine-κ2N,N′)bis(tri(p-tolyl)phosphine-κP)copper(I) tetrafluoroborate – 4,4′-bipyridine (2/1), C57H54BCuF4N3P2
  56. The crystal structure of 2,6-dimethyl-3,5-dinitrocyclohexa-2,5-diene-1,4-dione, C8H6N2O6
  57. The crystal structure of 2,3-dimethyl-1,4-dinitrobenzene – a Z′ = 4 structure, C8H8N2O4
  58. Crystal structure of [(1,2-η)-1,2,3,4,5-pentamethyl-cyclopenta-2,4-dien-1-yl] (1,4,10,13-tetraoxa-7,16-diazacyclooctadecane-κ6N2,O4) rubidium (I), [Rb(diaza-18-crown-6)]Cp*, C22H41N2O4Rb
  59. Crystal structure of 2-(4-fluorophenyl)-N-phenyl-2-(phenylamino)ethanesulfonamide – toluene (1/0.5), C23.5H23FN2O2S
  60. Crystal structure of pyrene-4-aldehyde, C17H10O
  61. Crystal structure of 2-(furan-2-yl)-5-methyl-1,3-dioxane-5-carboxylic acid, C10H12O5
  62. Crystal structure of 2-(4-chlorophenyl)-3-phenyl-1,8-naphthyridine, C20H13N2Cl
  63. Crystal structure and photochromism of 1-(2-ethyl-5-formylthiophen-3yl)-2-(2-cyano-1,5-dimethyl-4-pyrrl)-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C19H14F6N2OS
  64. Crystal structure of 2-(4-bromophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16BrIN2
  65. Crystal structure of 2-(4-(dimethylamino)phenyl)-10-methylacridin-9(10H)-one, C22H20N2O
  66. Crystal structure of 4-(acetoxymethyl)-6-(3-acetyl-3-(4-fluorophenyl)thioureido)cyclohex-4-ene-1,2,3-triyl triacetate, C24H26FN2O9S
Heruntergeladen am 21.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2018-0301/html
Button zum nach oben scrollen