Startseite Crystal structure of 1,3-dimethyl-2-(p-tolyl)-1H-perimidin-3-ium iodide 1.5 hydrate, C20H22IN2O1.5
Artikel Open Access

Crystal structure of 1,3-dimethyl-2-(p-tolyl)-1H-perimidin-3-ium iodide 1.5 hydrate, C20H22IN2O1.5

  • Lin Yuan , Zhong-Yan Li EMAIL logo , Xian-You Yuan und Min Zhang
Veröffentlicht/Copyright: 8. August 2018

Abstract

C20H22IN2O1.5, monoclinic, C2/c (no. 15), a = 38.828(4) Å, b = 9.5689(9) Å, c = 26.186(2) Å, β = 127.719(1)°, Z = 8, V = 7696.0(12) Å3, Rgt(F) = 0.0379, wRref(F2) = 0.1058, T = 296(2) K.

CCDC no.: 1472982

The 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, colorless
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.68 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω-scans
θmax, completeness:25°, >99%
N(hkl)measured, N(hkl)unique, Rint:35774, 6781, 0.018
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 5614
N(param)refined:448
Programs:Bruker programs [1], SHELX [2, 3]
Table 2:

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

AtomxyzUiso*/Ueq
I2−0.079488(9)0.98965(3)0.020967(15)0.07124(12)
I10.164420(10)0.36573(4)0.309302(15)0.07974(13)
O2−0.03783(19)0.2095(5)0.1576(2)0.1342(17)
H2A−0.01360.20910.19530.201*
H2B−0.03630.15590.13320.201*
N10.01707(9)0.7558(3)0.07866(14)0.0492(7)
N2−0.02088(11)0.6172(4)0.10198(16)0.0590(8)
N3−0.18228(9)0.8937(3)−0.15015(14)0.0463(7)
C5−0.06228(15)0.6206(6)−0.1137(2)0.0773(14)
H5−0.07980.5913−0.15660.093*
C6−0.06783(12)0.5627(5)−0.0705(2)0.0662(12)
C1−0.04127(11)0.6118(4)−0.00493(18)0.0519(9)
C2−0.00965(11)0.7131(4)0.01290(17)0.0509(8)
C120.01034(11)0.7107(4)0.11965(18)0.0515(8)
C140.03907(12)0.7594(4)0.18777(18)0.0542(9)
C150.03324(17)0.8884(6)0.2047(2)0.0874(16)
H150.01070.94630.17370.105*
C160.06129(18)0.9309(6)0.2685(2)0.0947(18)
H160.05681.01690.28010.114*
C170.09582(14)0.8488(5)0.3153(2)0.0687(12)
C200.12821(18)0.9053(8)0.3836(2)0.0993(19)
H20A0.14240.98640.38280.149*
H20B0.14950.83490.41050.149*
H20C0.11310.93020.40060.149*
C130.05114(14)0.8595(5)0.0980(2)0.0667(11)
H13A0.06830.82730.08530.100*
H13B0.06950.87170.14390.100*
H13C0.03780.94710.07720.100*
C11−0.03097(19)0.5807(7)0.1463(3)0.0955(17)
H11A−0.02060.48810.16280.143*
H11B−0.06190.58430.12340.143*
H11C−0.01700.64600.18150.143*
C10−0.04721(12)0.5593(4)0.0390(2)0.0585(10)
C9−0.07704(15)0.4560(5)0.0215(3)0.0837(15)
H9−0.08070.41980.05090.100*
C8−0.10241(15)0.4057(6)−0.0435(3)0.0947(19)
H8−0.12230.3342−0.05590.114*
C7−0.09848(15)0.4576(6)−0.0869(3)0.0870(16)
H7−0.11640.4238−0.12890.104*
C180.10090(14)0.7214(5)0.2975(2)0.0663(11)
H180.12380.66410.32850.080*
C190.07292(14)0.6756(5)0.23470(19)0.0615(10)
H190.07680.58770.22380.074*
C3−0.00445(14)0.7657(5)−0.0302(2)0.0659(11)
H30.01690.8321−0.01740.079*
C4−0.03175(17)0.7183(6)−0.0940(2)0.0821(14)
H4−0.02860.7559−0.12370.099*
C25−0.17093(13)1.2183(5)−0.24712(19)0.0614(10)
H25−0.16881.2895−0.26920.074*
C24−0.15646(14)1.0879(5)−0.2457(2)0.0651(11)
H24−0.14451.0717−0.26690.078*
C23−0.15906(13)0.9769(4)−0.21310(19)0.0570(9)
H23−0.14960.8880−0.21360.068*
C22−0.17574(11)1.0019(4)−0.18056(17)0.0462(8)
C32−0.19358(10)0.9213(4)−0.11245(16)0.0453(8)
C34−0.20099(12)0.8063(4)−0.08252(17)0.0502(8)
C39−0.24237(13)0.7961(5)−0.0990(2)0.0643(11)
H39−0.26340.8627−0.12590.077*
C38−0.25224(15)0.6872(5)−0.0756(2)0.0739(12)
H38−0.28010.6809−0.08710.089*
C37−0.22143(16)0.5866(5)−0.0351(2)0.0670(11)
C40−0.2330(2)0.4671(6)−0.0103(3)0.0951(17)
H40A−0.22950.49640.02770.143*
H40B−0.21420.38920.00000.143*
H40C−0.26270.4399−0.04290.143*
C27−0.20642(12)1.3776(4)−0.21622(19)0.0599(10)
H27−0.20631.4512−0.23930.072*
C26−0.18931(11)1.2466(4)−0.21521(17)0.0521(9)
C33−0.17779(17)0.7502(4)−0.1652(2)0.0686(11)
H33A−0.19180.7425−0.21050.103*
H33B−0.19120.6866−0.15370.103*
H33C−0.14750.7277−0.14110.103*
C35−0.16969(13)0.7085(4)−0.0410(2)0.0604(10)
H35−0.14170.7155−0.02890.072*
C36−0.18009(15)0.6008(5)−0.0176(2)0.0663(11)
H36−0.15870.53620.01060.080*
N4−0.20240(9)1.0517(3)−0.10570(14)0.0473(7)
C31−0.20382(15)1.0908(5)−0.05240(19)0.0626(10)
H31A−0.23341.1090−0.06940.094*
H31B−0.18661.1732−0.03140.094*
H31C−0.19241.0156−0.02180.094*
C30−0.20565(10)1.1629(4)−0.14404(16)0.0454(8)
C21−0.19002(10)1.1365(4)−0.17953(16)0.0446(8)
C29−0.22229(12)1.2903(4)−0.1464(2)0.0565(9)
H29−0.23301.3063−0.12350.068*
C28−0.22303(13)1.3972(4)−0.1839(2)0.0629(11)
H28−0.23521.4832−0.18660.076*
O10.04859(19)0.3069(7)0.2480(3)0.158(2)
H1A0.07580.34220.29170.236*
H1B0.05260.23710.27350.236*
O3−0.1282(3)0.3201(10)0.0871(4)0.251(4)
H3A−0.10820.25970.10110.376*
H3B−0.14440.29600.09730.376*

Source of material

Iodomethane (3.02 g, 0.021 mol) was added dropwise to a solution of 1-methyl-2-(p-tolyl)-1H-perimidine (2.72 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 ethanol and dried under vacuum to give the title compound (3.11 g, 75%). Yellow needle crystals were obtained by recrystallization from ethyl acetate.

Experimental details

The methyl groups refined using rigid groups allowed to rotate about the N—C bond (AFIX 137 option of the SHELX program). The Uiso values of the hydrogen atoms of methyl groups were set to 1.5Ueq(C) and the Uiso values of other hydrogen atons were set to 1.2Ueq(C).

Discussion

Perimidines have drawn extensive examinations [4], [5]. There are several preparative methods for the synthesis of perimidine derivatives [6], [7].

There are two cations, two anions and three water molecules in the asymmetric unit. In its 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 121.5(3), 119.7(3) and 118.7(3) in turn, which indicates the sp2 hybridization state of C(12) atom and the new-formed three-membered heterocyclic ring is essentially planar. Geometric parameteres are in accord with those of other compounds of this class reported by us [8].

Acknowledgements

This work was financially supported by the Natural Science Foundation of Hunan Province of China (2017JJ3093).

References

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Received: 2018-04-16
Accepted: 2018-07-11
Published Online: 2018-08-08
Published in Print: 2018-11-27

©2018 Lin Yuan 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 di-μ2-aqua-tetraaqua-bis(4-(1H-1,2,4-triazol-1-yl)benzoato-κN)disodium(I) C18H24N6Na2O10
  3. Crystal structure of diaqua-bis(2-bromo-4-chloro-6-formylphenolato-κ2O,O′)cobalt(II), C16H16Cl2CrN3O7
  4. Crystal structure of catena-poly[(μ2-1-(4-(1H-pyrazol-1-yl)phenyl)ethan-1-one-κ2N:O)-bis(1,1,1-trifluoro-4-oxo-4-(thiophen-2-yl)but-2-en-2-olato-κ2O,O′)copper(II)], C27H18CuF6N2O5S2
  5. Crystal structure of ethyl 2-amino-4-(3,5-difluorophenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carboxylate, C18H15F2NO5
  6. Crystal structure of 5,5′-dimethoxy-2,2′-[1,1′-(ethylenedioxydinitrilo)diethylidyne]diphenol, C20H24N2O6
  7. Crystal structure of (E)-1-(4-(((E)-3,5-dichloro-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H14Cl2N2O2
  8. Crystal structure of 2,3,9,10,16,17,23,24-octakis(2,6-dimethylphenoxy)phthalocyanine - trichloromethane (1/2), C98H84Cl6N8O8
  9. Crystal structure of methyl 2-((1-(2-(methoxycarbonyl)benzyl)-1H-1,2,3-triazol-4-yl)methoxy)-1-naphthoate, C24H21N3O5
  10. Crystal structure of catena-poly[(μ2-3,3′-thiodipropionato-κ2O:O′)-(bipyridine-κ2N,N′)copper(II)] C16H16CuN2O4S
  11. Crystal structure of [4-chloro-2-(((2-((3-ethoxy-2-oxidobenzylidene)amino)phenyl)imino)(phenyl)methyl)phenolato-κ4N,N′,O,O′}nickel(II) - ethyl acetate (1/1), C32H29ClN2NiO5
  12. Crystal structure of (4-(4-chlorophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κ2O,O′)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, C29H52Cl2N4NiO9
  13. Crystal structure of ethyl 2-amino-4-(3,4-dimethylphenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carboxylate, C20H21NO5
  14. Structure and photochromism of 1,2-bis[2-methyl-5-(3-quinolyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C33H20F6N2S2
  15. Crystal structure of catena-poly[diaqua-bis(μ2-3,5-di(1H-1,2,4-triazol-1-yl)benzoate-κ2N:N′)cobalt(II))] 2.5 hydrate, C22H23CoN12O8.50
  16. The crystal structure of dichlorido(1,3-dimesityl-1H-3λ4-imidazol-2-yl)(morpholine-κN)palladium(IV), C25H33Cl2N3OPd
  17. Crystal structure of catena-poly[bis(4,4′-dipyridylaminium-kN)-(μ2-germanowolframato-κ2O:O′)-(2,2′-bipyridine-κ2N,N′)copper(II)] with a Keggin-type heteropolyoxoanion, [Cu(C10H8N2)(C10H10N3)2][GeW12O40] ⋅ H2O
  18. Crystal structure of diaqua-(N-(1-(pyrazin-2-yl)ethylidene)pyridin-1-ium-4-carbohydrazonate-κ3N,N′,O)-tris[nitrato-κ2O,O′)lanthanum(III), C12H15N8O12La
  19. The crystal structure of 2-hydroxy-4-((2-hydroxy-4-methoxy-3,6-dimethylbenzoyl)oxy)-3,6-dimethylbenzoic acid–methanol (1/1), C20H24O8
  20. Crystal structure of guanidinium tetrapropylammonium bis(hydrogencarbonate) dihydrate, C15H40N4O8
  21. Crystal structure of (Z)-2-bromo-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-phenylprop-2-en-1-one, C23H27BrO2
  22. Crystal structure of 2-(4-(4H-1,2,4-triazol-4-yl)phenyl)acetic acid, C10H9N3O4
  23. Crystal structure of 4,4′-(1,4-phenylene)bis(1H-imidazol-3-ium)bis(2-carboxybenzoate), C30H26N4O8
  24. Crystal structure of 4,4′-(4,10-diphenyl-4,10-dihydropyreno[4,5-d:9,10-d′]diimidazole-5,11-diyl)bis(N,N-diphenylaniline), C66H44N6
  25. Crystal structure of catena-poly[diaqua-bis(μ2-5-(3-(1H-imidazol-5-yl)phenyl)tetrazol-2-ido-κ2N:N′)cobalt(II)], C20H18CoN12O2
  26. Crystal structure of 1,3-dimethyl-2-(p-tolyl)-1H-perimidin-3-ium iodide 1.5 hydrate, C20H22IN2O1.5
  27. Crystal structure of 2-(4-methoxyphenyl)chromane, C16H16O2
  28. Crystal structure of poly[(μ2-2-carboxy-5-nitroisophthalato-κ2O:O′)-(μ2-4-((1H-imidazol-1-yl)methyl)pyridine-κ2N:N′)zinc(II)], C18H12N4O8Zn
  29. Crystal structure of bis(1-((2-ethyl-4-methyl-1H-imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κ2N:N′)tetraiodidodicadmium(II), [Cd2(C13H15N5)2I4]
  30. Crystal structure of tetramethylammonium bis(acetato-κ1O)-tetrakis(μ3-3-((hydroxyimino)methyl)-5-methoxy-2-oxidobenzoate-κ5O,O′:O′,N:O′′)tetrazinc(II) — N,N′-dimethylformamide — water (1/2/2), C62H96Zn4N10O28
  31. Crystal structure of poly[(μ4-5-tert-butylisophthalato-κ4O:O′:O′′:O′′′)-(1,3-dimethyl-2-imidazolidinone-κO)zinc(II)] C17H22N2O5Zn
  32. Crystal structure of [tris(2-benzimidazolylmethyl)amine-κ4N,N′,N′′,N′′′]-[(pyridine-2,6-dicarboxylato-κ2O,N)]cadmium(II)–methanol (1:3) C34H36CdN8O7
  33. The crystal structure of bis(1H-benzo[d]imidazol-2-amine-κN)-diiodidocadmium(II), C14H14CdI2N6
  34. Crystal structure of tetrakis(1H-benzimidazol-2-amine)-κN)-bis(μ2-sulfonato-κ2O:O′)dizinc(II) - methanol (1/1), C30H36N12O10S2Zn2
  35. Crystal structure of 3β-methoxy-20α-dimethylamino-pregn-5-ene, C24H41NO
  36. Crystal structure of dimethyl 4,4′-oxydibenzoate, C16H14O5
  37. Crystal structure of catena-poly[diiodido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-3-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O)zinc(II)], C17H16I2N4OZn
  38. Crystal structure of 4-((E)-((E)-5-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-4-oxopiperidin-3-ylidene)methyl)benzonitrile, C26H18F2N2O3S
  39. Crystal structure of bis(acetato-κ1O)-bis(1-(pyridin-2-yl)ethan-1-one oxime-κ2N,N′)zinc(II), C18H22N4O6Zn
  40. The crystal structure of 9-butoxy-2-(hydroxymethyl)-2H-imidazo[1,5-a]quinolin-10-ium bromide, C17H21O2N2Br
  41. Crystal stucture of 2-(tert-butyl)-6-(hydroxymethyl)-4-methylphenol, C12H18O2
  42. Crystal structure of catena-poly[(2-(5-chloroquinolin-8-yloxy)-1-(pyrrolidin-1-yl)ethan-1-one-κ3N,O,O′)-(dinitrato-κ2O,O′)mercury(II)], C15H15N4O8ClHg
  43. Crystal structure of dimethyl (3aS,6R,6aS,7S)-1H,3H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isochromene-3a1,6a-dicarboxylate, C16H16O7
  44. The crystal structure of 2-(dimethoxymethyl)-4-(4-methylphenyl)-1H-imidazole—petroleum ether-chloroform (3/1), C27H33Cl3N4O4
  45. Crystal structure of 8-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carbaldehyde, C9H5F3N2O
  46. The crystal structure of N,N-diethyl-4,6-bis(naphthalen-2-yloxy)-1,3,5-triazin-2-amine, C27H24N4O2
  47. Crystal structure of 5-bromo-7-chloro-3,3a-dihydrocyclopenta[b]chromen-1(2H)-one, C12H8BrClO2
  48. Crystal structure of 2-(bis(4-fluorophenyl)methylene)hydrazine-1-carbothioamide, C14H11F2N3S
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