Home Crystal structure of N-(diaminomethylene)-1-(dimethylamino)-1-iminiomethanaminium dichloride, C4H13Cl2N5
Article Open Access

Crystal structure of N-(diaminomethylene)-1-(dimethylamino)-1-iminiomethanaminium dichloride, C4H13Cl2N5

  • Yu-Pei Xia ORCID logo EMAIL logo
Published/Copyright: June 7, 2023

Abstract

C4H13Cl2N5, monoclinic, P21 (no. 4), a = 7.1868(6) Å, b = 5.8408(4) Å, c = 12.6534(11) Å, β =  105.134 ( 2 ) , V = 512.73(7) Å3, Z = 2, R gt(F) = 0.0354, wR ref(F 2) = 0.0961, T = 298 K.

CCDC no.: 2259709

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: Colourless block
Size: 0.50 × 0.47 × 0.46 mm
Wavelength: Mo radiation (0.71073 Å)
μ: 0.59 mm−1
Diffractometer, scan mode: Bruker Smart CCD 6000, φ and ω
θ max, completeness: 28.4°, 99 %
N(hkl)measured, N(hkl)unique, R int: 3305, 2382, 0.035
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 2268
N(param)refined: 103
Programs: Bruker [1], Olex2 [2], Shelx [3, 4]
Table 2:

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

Atom x y z U iso*/U eq
C1 −0.4706 (5) −0.2228 (6) 0.7169 (3) 0.0444 (7)
H1A −0.415971 −0.371277 0.737610 0.067*
H1B −0.441084 −0.175112 0.650455 0.067*
H1C −0.607927 −0.229900 0.705353 0.067*
C2 −0.4158 (6) −0.1130 (8) 0.9128 (3) 0.0598 (12)
H2A −0.540060 −0.181902 0.904399 0.090*
H2B −0.407448 0.024582 0.955346 0.090*
H2C −0.317222 −0.217948 0.949508 0.090*
C3 −0.2648 (4) 0.1060 (5) 0.7946 (2) 0.0303 (6)
C4 −0.0943 (4) 0.2179 (5) 0.6582 (2) 0.0311 (6)
Cl1 0.07056 (11) 0.67390 (13) 0.85708 (6) 0.0431 (3)
Cl2 0.33337 (9) 0.30461 (12) 0.55093 (5) 0.0369 (2)
N1 −0.3892 (4) −0.0572 (5) 0.8045 (2) 0.0365 (6)
N2 −0.1567 (4) 0.2194 (5) 0.8788 (2) 0.0390 (6)
H2D −0.164402 0.189245 0.944057 0.047*
H2E −0.078514 0.323250 0.868395 0.047*
N3 −0.2598 (3) 0.1716 (5) 0.69010 (19) 0.0367 (6)
H3 −0.368037 0.184353 0.641486 0.044*
N4 −0.1068 (4) 0.3607 (5) 0.5753 (2) 0.0407 (6)
H4A −0.006283 0.390569 0.552836 0.049*
H4B −0.215358 0.423575 0.543873 0.049*
N5 0.0688 (4) 0.1192 (5) 0.7078 (2) 0.0398 (6)
H5A 0.171062 0.146583 0.686744 0.048*
H5B 0.073526 0.027053 0.761466 0.048*

1 Source of materials

3-(Diaminomethylidene)-1,1-dimethylguanidine hydrochloride (metformin·HCl) was purchased from Shanghai Aladdin Biochemical Technology Co., Ltd. Under stirring, 1 g (6.038 mmol) of metformin · HCl was added to a mixed solution of concentrated hydrochloric acid and CH3OH (10 mL, 5:5, v/v). The mixture was heated to 40 °C, and then filtered. Colorless block crystals were obtained by slow evaporation within 1 week, yielding 65 % (based on the metformin·HCl).

2 Experimental details

The raw frame of the title structure was solved by the Shelxt program and refined with the Shelxl program, respectively. H atoms were placed in their idealized positions with isotropic thermal parameters. The bond length of H2B–H2D was fixed to 2.100 Å with the command DFIX.

3 Comment

The salt 3-(diaminomethylidene)-1,1-dimethylguanidine hydrochloride (metformin·HCl), is a famous hypoglycemic drug and is able to construct crystal structures with inorganic and organic components [5], [6], [7], [8]. However, only a limited number of metformin-based crystal structures were reported. To extend the family of the metformin-based structures, the title metformin·2HCl was synthesized. The asymmetric unit contains one protonated metformin molecule and two free chlorine anions (Cl1 and Cl2). The distances of N2–C3 and N3–C4 are 1.321(4) and 1.378(3) Å, respectively. All the N–C bond lengths are within the normal range of 1.310(4)–1.473(4), comparable to the reported metformin-based structures [9], [10], [11], [12]. The protonated metformin molecules are linked by the free chlorine anions through N–H⋯Cl hydrogen bonding interactions (N2–H2D⋯Cl11−x,1/2+y,−z , N2–H2E⋯Cl1−1+x,1+y,z , N3–H3⋯Cl21−x,1/2+y,1−z , N4–H4A⋯Cl2x,1/2+y,1−z , N4–H4B⋯Cl2 x,1+y,z , N5–H5A⋯Cl2x,1/2+y,1−z , N5–H5B⋯Cl1−1+x,y,z ) and finally resulted in a 3D network.


Corresponding author: Yu-Pei Xia, College of Chemistry and Chemical Engineering, Weifang University, Weifang, Shandong 261061, P.R. China, E-mail:

  1. Author contributions: The author has accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: Research Fund for the Doctoral Program of Weifang University (No. 2021BS09).

  3. Conflict of interest statement: The author declares no conflicts of interest regarding this article.

References

1. Bruker. Saint and Sadabs; Bruker AXS Inc.: Madison, Wisconsin, USA, 2000.Search in Google Scholar

2. Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K., Puschmann, H. Olex2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 2009, 42, 339–341; https://doi.org/10.1107/s0021889808042726.Search in Google Scholar

3. Sheldrick, G. M. Crystal structure refinement with Shelxl. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Search in Google Scholar

4. Sheldrick, G. M. Shelxtl – integrated space-group and crystal-structure determination. Acta Crystallogr. 2015, A71, 3–8; https://doi.org/10.1107/s2053273314026370.Search in Google Scholar PubMed PubMed Central

5. Olar, R., Badea, M., Marinescu, D., Chifiriuc, M.-C., Bleotu, C., Grecu, M. N., Iorgulescu, E.-E., Lazar, V. N,N-dimethylbiguanide complexes displaying low cytotoxicity as potential large spectrum antimicrobial agents. Eur. J. Med. Chem. 2010, 45, 3027–3034; https://doi.org/10.1016/j.ejmech.2010.03.033.Search in Google Scholar PubMed

6. Gopalakrishnan, D., Ganeshpandian, M., Loganathan, R., Bhuvanesh, N. S. P., Sabina, X. J., Karthikeyan, J. Water soluble Ru(II)-arene complexes of the antidiabetic drug metformin: DNA and protein binding, molecular docking, cytotoxicity and apoptosis-inducing activity. RSC Adv. 2017, 7, 37706–37719; https://doi.org/10.1039/c7ra06514k.Search in Google Scholar

7. Hariharan, M., Rajan, S. S., Srinivasan, R. Structure of metformin hydrochloride. Acta Crystallogr. 1989, C45, 911–913; https://doi.org/10.1107/s0108270188014246.Search in Google Scholar

8. Villamizar-Delgado, S., Porras-Osorio, L. M., Piñeros, O., Ellena, J., Balcazar, N., Varela-Miranda, R. E., D’vries, R. F. Biguanide-transition metals complexes as potential drug for hyperglycemia treatment. RSC Adv. 2020, 10, 22856–22863; https://doi.org/10.1039/d0ra04059b.Search in Google Scholar PubMed PubMed Central

9. Tomas, A., Morgant, G., Nguyen-Huy, D., Lemoine, P., Viossat, B. Crystal structure of tetrachloro(metformin)platinum(IV)–dimethylformamide (1:2), C4N5H11PtCl4·2(CH3)2NCHO. Z. Kristalogr. N. Cryst. Struct. 2002, 217, 131–132; https://doi.org/10.1524/ncrs.2002.217.jg.131.Search in Google Scholar

10. Lemoine, P., Chiadmi, M., Bissery, V., Tomas, A., Viossat, B. Les Composés de la metformine avec les Ions CoII, CuII et NiII. Acta Crystallogr. 1996, C52, 1430–1436; https://doi.org/10.1107/s0108270195008377.Search in Google Scholar

11. Chen, F., Moat, J., Mcfeely, D., Clarkson, G., Hands-Portman, I. J., Furner-Pardoe, J. P., Harrison, F., Dowson, C. G., Sadler, P. J. Biguanide iridium(III) complexes with potent antimicrobial activity. J. Med. Chem. 2018, 61, 7330–7344; https://doi.org/10.1021/acs.jmedchem.8b00906.Search in Google Scholar PubMed

12. Ramadan, A. E.-M. M., Shaban, S. Y., Ibrahim, M. M., Sallam, S. A., El-Shami, F. I., Al-Juaid, S. Metformin-based copper(II) complexes: synthesis, structural characterization and mimicking activity of catechol oxidase and phenoxazinone synthase. J. Mater. Sci. 2020, 55, 6457–6481; https://doi.org/10.1007/s10853-019-04165-5.Search in Google Scholar

Received: 2023-05-05
Accepted: 2023-05-24
Published Online: 2023-06-07
Published in Print: 2023-08-28

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

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

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of a polymorph of potassium picrate, C6H2KN3O7
  4. The crystal structure of (1E,2E)-1,2-bis(quinolin-2-ylmethylene)hydrazine, C20H14N4
  5. 5-Amino-2-chloro-4-fluoro-N-(N-isopropyl-N-methylsulfamoyl) benzamide, C11H15O3ClFN3S
  6. Crystal structure of trans-N 1,N 8-bis(2-cyanoethyl)-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, C22H42N6
  7. The crystal structure of [N-{[2-(oxy)-4-methoxyphenyl](phenyl)methylidene}alaninato]-diphenyl-silicon(IV) – chloroform (1/1), C29H25NO4Si·CHCl3
  8. Crystal structure of tetracarbonyl-{μ-[N-(diphenylphosphanyl)-N,P,P-triphenylphosphinous amide]}-bis[μ-(phenylmethanethiolato)]diiron (Fe–Fe), C48H39Fe2NO4P2S2
  9. Crystal structure of baryte from Mine du Pradet (France)
  10. The crystal structure of [(2,2′-bipyridine-6-carboxylato-κ3 N,N,O)-(6-phenylpyridine-2-carboxylate-κ2 N,O)copper(II)] monohydrate, C23H17N3O5Cu
  11. Crystal structure of bis(μ-benzeneselenolato)-(μ-[N-benzyl-N-(diphenylphosphanyl)-P,P-diphenylphosphinous amide])-tetracarbonyl diiron (Fe–Fe), C47H37Fe2NO4P2Se2
  12. The crystal structure of diaqua-methanol-κ1 O- (3-thiophenecarboxylato-κO)-(2,2′-dipyridyl-κ2 N,N′)manganese(II) 3-thiophenecarboxylate, C21H22N2O7S2Mn
  13. Crystal structure of catena-poly[tetrakis(butyl)-μ2-2-((oxido(phenyl)methylene)hydrazineylidene)propanoato-κ4 O:O,O′,N-μ2-2-((oxido(phenyl)methylene)hydrazineylidene)propanoato-κ4 O,N,O′:N′-ditin(IV)], C34H50N6O6Sn2
  14. Crystal structure of 4-chloro-N′-[(1E)-(2-nitrophenyl)methylidene]benzohydrazide, C14H10ClN3O3
  15. The crystal structure of 3-(1′-deoxy-3′,5′-O-dibenzy-β-d-ribosyl)adenine dichloromethane solvate, C49H52Cl2N10O6
  16. The crystal structure of (Z)-4-amino-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H17N3O
  17. The co-crystal structure of etoricoxib–phthalic acid (1/1), C18H15ClN2O2S·C8H6O4
  18. Crystal structure of (glycinto-κ 2 O,N )-[5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ 4 N,N ,N ,N ]nickel(II) perchlorate monohydrate C18H42ClN5NiO7
  19. The crystal structure of catena-poly[bis(1-ethylimidazole-k1 N)-(μ 2-benzene-1-carboxyl-3,5-dicarboxylato-κ 2 O, O′)zinc(II)], C19H20N4O6Zn
  20. Crystal structure of 3-(thiazol-2-ylcarbamoyl)-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid, C11H12N2O4S
  21. Rietveld structure analysis of keatite, a rare, metastable SiO2 polymorph
  22. Crystal structure of catena-poly[(μ2-isophthalato-k3 O,O′:O″)(4-(4-pyridyl)-2,5-dipyrazylpyridine-k3 N,N′,N″)cobalt(II)] trihydrate C26H22N6O7Co1
  23. Crystal structure of 3,5–di-O-benzoyl-1,2-O-isopropylidene-α–D-ribose, C22H22O7
  24. The crystal structure of fac-tricarbonyl(6-bromo-2,2-bipyridine-κ2 N,N)-(nitrato-κO)rhenium(I), C13H7BrN3O6Re
  25. The crystal structure of (E)-N′-(4-hydroxy-3-methoxybenzylidene)-2-naphthohydrazide monohydrate, C19H18N2O4
  26. The crystal structure of 5,5′-diselanediyl-bis(2-hydroxybenzaldehyde), C14H10O4Se2
  27. The crystal structure of catena-poly[diaqua-m2-dicyanido-κ2 C:N-dicyanido-κ1 C-bis(4-(pyridin-4-yl)benzaldehyde-κ1N)iron(II)-platinum(II), C28H22N6O4PtFe
  28. Redetermination of the crystal structure of 5,14-dihydro-6,17-dimethyl-8,15-diphenyldibenzo(b,i)(1,4,8,11)tetra-azacyclotetradecine, C32H28N4
  29. Crystal structure of poly[(μ3-2-(3,5-dicarboxyphenyl) benzimidazole-6-carboxylato-κ4O:O:O′:O″)lead(II)] monohydrate, C16H10N2O7Pb
  30. The crystal structure of fac-tricarbonyl(2-pyridin-2-yl-quinoline-κ2 N,N′)-(pyrazole-κN)rhenium(I)nitrate, C20H14N4O3ReNO3
  31. Crystal structure of dibromo-dicarbonyl-bis(tricyclohexylphosphine)-osmium(II) dichloromethane solvate, C38H66Br2O2OsP2
  32. Crystal structure of poly[bis(μ 2-2,6-bis(1-imidazoly)pyridine-κ 2 N:N′)copper(II)] diperchlorate dihydrate, C22H22Cl2CuN10O10
  33. The crystal structure of fac-tricarbonyl(N-benzoyl-N,N-cyclohexylmethylcarbamimidothioato-κ2 S,O)-(pyridine-κN)rhenium(I), C23H24N3O4ReS
  34. Crystal structure of (E)-7-fluoro-2-(4-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C17H12F2O
  35. Synthesis and crystal structure of 1-((3R,10S,13S, 17S)-3-((2-methoxyphenyl)amino)-10,13-dimethylhexadecahydro-1H-cyclopenta[α]phenanthren-17-yl)ethan-1-one, C28H41NO2
  36. The crystal structure of fac-tricarbonyl((pyridin-2-yl)methanamino-κ2 N,N′)-((pyridin-2-yl)methanamino-κN)rhenium(I) nitrate, C15H16O3N4Re
  37. The crystal structure of (1-(pyridin-2-yl)-N-(pyridin-2-ylmethyl)-N-((1-(4-vinylbenzyl)-1H-benzo[d]imidazol-2-yl)methyl)methanamine-κ 4 N,N′,N″,N‴)tris(nitrato-kO,O′)-erbium(III), C29H27ErN8O9
  38. Crystal structure of tetracene-5,12-dione, C18H10O2
  39. Crystal structure of (3R,3aS,6R,6aR)-6-hexyl-3-methyltetrahydrofuro[3,4-b]furan-2,4-dione, C13H20O4
  40. The crystal structure of N1,N3-bis((E)-thiophen-2-ylmethylene)isophthalohydrazide monohydrate, C18H16N4O3S2
  41. Crystal structure of methyl ((4-aminobenzyl)sulfonyl)-L-prolinate, C13H18N2O4S
  42. Crystal structure of (E)-3-(3-methoxybenzylidene)benzofuran-2(3H)-one, C16H12O3
  43. Synthesis and crystal structure (E)-1-(4-bromo-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one, C11H12BrNO2
  44. Synthesis and crystal structure of (S,E)-4-hydroxy-3-(2-((4aR,6aS,7R,10aS,10bR)-3,3,6a,10b-tetramethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethylidene)dihydrofuran-2(3H)-one, C23H34O5
  45. The crystal structure of N,N′-(1,2-phenylene)bis (2-((2-oxopropyl)selanyl)benzamide), C26H24N2O4Se2
  46. The crystal structure of 1-ethyl-2-nitro-imidazole oxide, C5H7N3O3
  47. The crystal structure of 2-(2-fluorophenyl)naphtho[2,1-d]thiazole, C17H10FNS
  48. Crystal structure of (E)-2,4-di-tert-butyl-6-(((2-fluorophenyl)imino) methyl)phenol, C21H26FNO
  49. Synthesis and crystal structure of 3-methyl-2-(methylthio)-4H-chromen-4-one, C12H12O2S
  50. Crystal structure of dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene-5,10-dione, C14H4O2S4
  51. The crystal structure of dimethyl 2,2ʹ-((adamantane-1,3-diylbis(4,1-phenylene)) bis(oxy))diacetate, C28H32O6
  52. The crystal structure of N-(6-chloro-2-methyl-2H-indazol-5-yl)acetamide, C10H10ClN3O
  53. Crystal structure of triaqua-(5-bromoisophthalato-κ1 O)-(2,2′-bipyridine-κ2 N:N′)nickel(II) hydrate, C18H19BrN2NiO8
  54. The crystal structure of 2-amino-4-carboxypyridin-1-ium perchlorate, C6H7ClN2O6
  55. The crystal structure of catena-poly[5-aminonicotinic acid-k1 N-m2-bromido-copper(I)], Cu(C6N2H6O2)Br
  56. The crystal structure of 2,2-bis(3-methoxyphenyl)-1-tosyl-1,2-dihydro- 4,3λ4  -[1,3,2]diazaborolo[4,5,1-ij]quinoline - dichloromethane (1/1)
  57. The crystal structure of catena-poly[bis(6-phenylpyridine-2-carboxylato-κ2 N,O)-(μ2-4,4′-bipyridne-κ2 N:N)cadmium(II)], C34H24N4O4Cd
  58. The crystal structure of 5,7-dinitropyrazolo[5,1-b]quinazolin-9(4H)-one, C10H5N5O5
  59. Crystal structure of rac-1,8-bis(2-carbamoylethyl)-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, C22H46N6O2
  60. The crystal structure of (E)-N -(2-bromobenzylidene)-2-naphthohydrazide, C36H26Br2N4O2
  61. The crystal structure of 5-nitronaphthoquinone, C10H5NO4
  62. The crystal structure of (S, R p )-4–benzhydrylideneamino-12-(4-tert-butyl oxazolin-2-yl)[2.2]paracyclophane, C36H36N2O
  63. Synthesis and crystal structure of 2-(2-oxo-2-(o-tolyl)ethyl)-4H-chromen-4-one, C18H14O3
  64. Crystal structure of 2-(thiazol-2-yl)hexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione, C11H10N2O3S
  65. Crystal structure of N-(diaminomethylene)-1-(dimethylamino)-1-iminiomethanaminium dichloride, C4H13Cl2N5
  66. Crystal structure of poly[(μ3-3, 5-dichloro-2-hydroxy-benzoato-κ4 Cl,O:O′:O″) silver(I)], C7H3AgCl2O3
  67. The crystal structure of tetrakis(1-isopropylimidazole-κ1 N)-[μ2- imidazole-4,5-dicarboxylato-κ4 O,N,O′,N′)]- trioxido-divanadium, C29H41N10O7V2
  68. Crystal structure of catena-[(μ3-bromido)-(1H-1,2,4-triazol-1-yl)benzoato-κ1 N)copper(I)], C9H7BrCuN3O2
  69. The crystal structure of (E)-4-fluoro-N′-(1-(2-hydroxyphenyl)propylidene)benzohydrazide, C16H15FN2O2
Downloaded on 7.9.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2023-0218/html
Scroll to top button