Home The crystal structure of N′,N″,2-tris((E)-5-chloro-2-hydroxybenzylidene)hydrazine-1-carbohydrazonhydrazide hydrochloride – methanol (1/3), C25H30Cl4N6O6
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The crystal structure of N′,N″,2-tris((E)-5-chloro-2-hydroxybenzylidene)hydrazine-1-carbohydrazonhydrazide hydrochloride – methanol (1/3), C25H30Cl4N6O6

  • An Zhan , E. Liu , Fangfang Jian EMAIL logo and Tongling Liang
Published/Copyright: August 3, 2022
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 237 Issue 5

Abstract

C25H30Cl4N6O6, triclinic, P 1 ‾ (no. 2), a = 9.2652(2) Å, b = 11.7642(3) Å, c = 14.6692(4) Å, α = 106.929(2)°, β = 99.753(2)°, γ = 98.675(2)°, V = 1473.15(7) Å3, Z = 2, R gt (F) = 0.0292, wRref (F 2) = 0.0839, T = 170 K.

CCDC no.: 2190507

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: Pink block
Size: 0.31 × 0.15 × 0.12 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 4.09 mm−1
Diffractometer, scan mode: XtaLAB Synergy R, ω
θ max, completeness: 77.3°, >99%
N(hkl)measured, N(hkl)unique, R int: 18,336, 5986, 0.020
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 5692
N(param)refined: 400
Programs: CrysAlisPRO [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
Cl1 0.66164 (5) 0.18556 (3) 0.12521 (3) 0.04561 (11)
Cl2 −0.09921 (4) 0.99436 (3) 0.20952 (3) 0.04146 (10)
Cl3 0.77613 (4) 0.96687 (3) 0.94730 (2) 0.04106 (10)
O1 0.88354 (11) 0.52448 (9) 0.67899 (7) 0.0360 (2)
H1 0.951147 0.498117 0.707228 0.054*
O2 0.26637 (12) 0.47623 (9) −0.01314 (7) 0.0367 (2)
H2 0.237084 0.449433 −0.074334 0.055*
O3 0.23621 (11) 1.17478 (8) 0.61925 (7) 0.0321 (2)
H3 0.202833 1.231584 0.652679 0.048*
N1 0.54046 (12) 0.65597 (9) 0.46849 (7) 0.0250 (2)
H1A 0.561322 0.588724 0.433015 0.030*
N2 0.59646 (11) 0.70307 (9) 0.56865 (7) 0.0242 (2)
N3 0.40530 (11) 0.68274 (9) 0.33138 (7) 0.0238 (2)
H3A 0.349003 0.722790 0.303578 0.029*
N4 0.44751 (11) 0.58122 (9) 0.27617 (7) 0.0242 (2)
N5 0.41405 (12) 0.81334 (9) 0.48564 (7) 0.0249 (2)
H5 0.447451 0.838692 0.549540 0.030*
N6 0.31906 (11) 0.87128 (9) 0.44088 (7) 0.0240 (2)
C1 0.45322 (13) 0.71731 (10) 0.42812 (8) 0.0217 (2)
C2 0.68857 (14) 0.64710 (11) 0.60325 (9) 0.0262 (2)
H2A 0.709754 0.576569 0.560963 0.031*
C3 0.76136 (13) 0.69054 (11) 0.70701 (9) 0.0252 (2)
C4 0.73543 (14) 0.79538 (11) 0.77063 (9) 0.0272 (3)
H4 0.667221 0.838575 0.747037 0.033*
C5 0.80885 (15) 0.83617 (12) 0.86769 (9) 0.0302 (3)
C6 0.90966 (16) 0.77488 (13) 0.90348 (10) 0.0363 (3)
H6 0.960310 0.804427 0.970474 0.044*
C7 0.93604 (15) 0.67087 (13) 0.84138 (10) 0.0346 (3)
H7 1.004783 0.628599 0.865735 0.041*
C8 0.86217 (14) 0.62765 (12) 0.74305 (10) 0.0281 (3)
C9 0.39335 (14) 0.54939 (11) 0.18402 (9) 0.0257 (2)
H9 0.332087 0.596329 0.159111 0.031*
C10 0.42423 (14) 0.44201 (11) 0.11654 (9) 0.0260 (2)
C11 0.51707 (14) 0.37243 (11) 0.14974 (9) 0.0279 (3)
H11 0.562633 0.394950 0.217312 0.033*
C12 0.54232 (16) 0.27096 (12) 0.08405 (10) 0.0326 (3)
C13 0.47444 (18) 0.23478 (13) −0.01452 (10) 0.0381 (3)
H13 0.491472 0.163695 −0.058655 0.046*
C14 0.38191 (17) 0.30248 (13) −0.04833 (10) 0.0354 (3)
H14 0.335284 0.277986 −0.115869 0.042*
C15 0.35678 (15) 0.40682 (12) 0.01657 (9) 0.0289 (3)
C16 0.28616 (14) 0.96367 (11) 0.49841 (9) 0.0257 (2)
H16 0.329460 0.989287 0.566521 0.031*
C17 0.18291 (13) 1.03014 (11) 0.46062 (9) 0.0248 (2)
C18 0.10420 (14) 0.98776 (11) 0.36259 (9) 0.0277 (3)
H18 0.121806 0.917093 0.318264 0.033*
C19 0.00126 (14) 1.04895 (12) 0.33078 (10) 0.0295 (3)
C20 −0.02548 (15) 1.15270 (12) 0.39405 (11) 0.0327 (3)
H20 −0.096956 1.193809 0.371023 0.039*
C21 0.05215 (15) 1.19622 (12) 0.49080 (10) 0.0312 (3)
H21 0.034503 1.267657 0.534124 0.037*
C22 0.15622 (14) 1.13545 (11) 0.52481 (9) 0.0259 (2)
Cl4 −0.13211 (3) 0.60410 (3) 0.24272 (2) 0.03116 (9)
O4 0.72925 (13) 0.50240 (9) 0.39093 (8) 0.0394 (2)
H4A 0.764360 0.524568 0.348195 0.059*
C23 0.7849 (2) 0.40109 (15) 0.40234 (13) 0.0447 (4)
H23A 0.728822 0.327590 0.349158 0.067*
H23B 0.773275 0.392190 0.465238 0.067*
H23C 0.891222 0.413050 0.400547 0.067*
O5 0.16415 (11) 0.72976 (10) 0.20877 (7) 0.0384 (2)
H5A 0.087527 0.701953 0.225399 0.058*
C24 0.1235 (2) 0.73236 (18) 0.11198 (12) 0.0506 (4)
H24A 0.051216 0.657412 0.071530 0.076*
H24B 0.212972 0.738943 0.084972 0.076*
H24C 0.078095 0.802526 0.112483 0.076*
O6a 0.44043 (16) 0.91932 (12) 0.69584 (9) 0.0378 (4)
H6Aa 0.401499 0.891210 0.734590 0.057*
C25a 0.5144 (6) 1.0382 (5) 0.7439 (4) 0.0496 (14)
H25Aa 0.581853 1.063958 0.705485 0.074*
H25Ba 0.572862 1.044965 0.808221 0.074*
H25Ca 0.441286 1.090370 0.752128 0.074*
O6Ab 0.5538 (5) 0.9895 (4) 0.6780 (3) 0.0375 (14)
H6AAb 0.610989 1.031171 0.655511 0.056*
C25Ab 0.523 (3) 1.057 (2) 0.7509 (19) 0.072 (7)
H25Db 0.485257 1.123396 0.734595 0.108*
H25Eb 0.613737 1.090115 0.803708 0.108*
H25Fb 0.446680 1.010026 0.772157 0.108*

  1. aOccupancy: 0.776 (3), bOccupancy: 0.224 (3).

Source of material

5-Chlorosalicylaldehyde (4.69 g, 0.01 mol) was placed in 15 mL ethanol at room temperature, then added into triaminoguanidine hydrochloride (1.40 g, 0.01 mol) solution containing 10 mL water and 8 mL ethanol. The mixture was heated and stirred at 65 °C for 3 h, and finally cooled to room temperature, Then remove the sediment was removed and the obtained filtrate stands for three days to precipitate light pink block crystals.

Experimental details

The crystal data collection was done on a XtaLAB Synergy R, HyPix diffractometer [1]. Using Olex2 [2], the structure was solved with the SHELXT [3] structure solution program and refined with the SHELXL [4] refinement package. All H-atoms were placed geometrically and refined using a riding model with common isotropic displacement factors U iso(H) = 1.2 or 1.5 U eq (parent C-atom).

Comment

As a good building block, triaminoguanidinium chloride and its derivatives are widely used in coordination chemistry [5, 6]. In addition, because triaminoguanidinium chloride contains rich N atoms and has good biological activity, it is also used in the research field of energetic materials [7] and biomedicine [8]. As far as we know, there are four reported structures of salts containing a triaminoguanidine-based Schiff base cation [10], [11], [12], [13]. We synthesized the title compound on the basis of previous studies.

The asymmetric units of the title compound include one [C22H18Cl3N6O3]+ cation, one Cl− anion and three solvent methanol molecules (see the figure). They are connected by O–H⋯Cl and N–H⋯O weak intermolecular hydrogen bonds, which makes the structure of the whole compound more stable. In the title compound, the bond lengths of N2=C2, N4=C9 and N6=C16 are 1.279 (2), 1.279(2) and 1.280(2) Å respectively. They are basically consistent with the reported C=N (1.279 Å) [9] double bond lengths of similar structures. Other bond lengths and bond angles are also within the normal range.

Corresponding author: Fangfang Jian, School of Chemical Engineering and Pharmaceutics, Henan University of Science and Technology, Luoyang Hekeda Recycling Energy Co. LTD., Luoyang, Henan 471003, P. R. China, E-mail:

Funding source: Henan University

Award Identifier / Grant number: 135100001

Acknowledgments

The authors would like to thank the financial supports from the Henan University of Science and Technology Distinguished Professor Open Fund (Grant No. 135100001).

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

  2. Research funding: Henan University of Science and Technology Distinguished Professor Open Fund (Grant No. 135100001).

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

References

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Received: 2022-06-16
Accepted: 2022-07-15
Published Online: 2022-08-03
Published in Print: 2022-10-26

© 2022 the author(s), published by De Gruyter, Berlin/Boston

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

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  53. Crystal structure of bis(μ2-2-oxido-2-phenylacetato-κ3 O,O′:O′)-bis(N-oxido-benzamide-κ2 O,O′)-bis(propan-2-olato-κ1 O)dititanium(IV), C36H38N2O12Ti2
  54. Crystal structure of poly[diaqua-(μ2-1H-benzo[d][1,2,3]triazole-5-carboxylato-κ2 O:O′)(μ2-oxalato-κ4O,O:O″,O′″)europium(III)] monohydrate, C9H10N3O9Eu
  55. Crystal structure of bis((N-methyl-2-oxyethyl)amine)-bis(μ 2-N,N,N-tris(2-oxoethyl)amine)-bis(isopropoxy)-bis(μ 3-oxo)tetratitanium(IV)– isopropanol (1/2), C34H76N4O16Ti4
  56. Synthesis and crystal structure of ethyl 4-((4-iodobenzyl)amino)benzoate, C16H16INO2
  57. Crystal structure of (Z)-2-(tert-butyl)-5-((5-(tert- butyl)-2H-pyrrol-2-ylidene)(mesityl)methyl)-1H-pyrrole, C26H34N2
  58. Crystal structure of dimethylammonium poly[μ4-1,1′-(1,4- phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato-κ6 N,O:O′:N′,O″:O‴) manganese(II)], C22H26MnN6O8
https://doi.org/10.1515/ncrs-2022-0308
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of 3-(1-(2-((5-methylthiophen-2-yl)methylene)hydrazinyl)ethylidene)chroman-2,4-dione, C17H14N2O3S
  4. Crystal structure of chlorido-(η 6-toluene)(5,5′-dimethyl-2,2′-bipyridine-κ2 N,N′)ruthenium(II) hexafluoridophosphate(V) ─ acetone (1/1) C22H26ClN2ORuPF6
  5. Crystal structure of 4-(((2-(3-(1-(3-(3-cyanophenyl)-6-oxopyridazin-1(6H)-yl)ethyl)phenyl) pyrimidin-5-yl)oxy)methyl)-1-methylpiperidin-1-ium chloride monohydrate, C30H33N6O2Cl
  6. The crystal structure of 2-chloro-N-((2-chlorophenyl)carbamoyl)nicotinamide, C13H9Cl2N3O2
  7. Crystal structure of 9-(t-butyl)-3,11-dihydro-6H-pyrazolo [1,5-a]pyrrolo[3′,2′:5,6]pyrido[4,3-d]pyrimidin-6-one hemihydrate, C30H32N10O3
  8. Crystal structure of di-μ2-hydroxido-tetrakis(6-methylpyridine-2-carboxylato-k2 N,O) diiron(III) trihydrate C28H32Fe2N4O13
  9. Crystal structure of catena-poly[qua-(μ2-2-aminoisophthalat-κ3 O,O′:O′′)(1,10-phenanthroline-κ2 N,N′)manganese(II)] C20H15MnN3O5
  10. Crystal structure of poly[(bis(isothiocyano)-bis(μ 2-(E)-N′-(pyridin-4-ylmethylene)isonicotinohydrazide))iron(II) – methanol – 1,4-dioxane (1/2/2), C36H44FeN10O8S2
  11. Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl)propylidene)-4-hydroxybenzohydrazide, C16H15ClN2O3
  12. Crystal structure of bis(μ2-benzoato-k2O:O′)-bis(μ2-benzoato-k3O,O′:O′)dinitrato-k2O,O′-bis(phenanthroline-k2 N,N′)dierbium(III), C52H36Er2N6O14
  13. Crystal structure of 4-ethyl-2-{[(4-nitrophenyl)methyl]sulfanyl}-6-oxo-1,6-dihydropyrimidine-5-carbonitrile, C14H12N4O3S
  14. Synthesis and crystal structure of 1-((3R,10S,13R,17S)-10,13-dimethyl-3- (phenylamino)hexadecahydro-1H-cyclopenta[α] phenanthren-17-yl)ethan-1-one, C27H39NO
  15. Crystal structre of 1,4-bis(bromomethyl)-2,3,5,6-tetramethylbenzene, C12H16Br2
  16. Crystal structure of 2-(adamantan-1-yl)-5-(3,5-dinitrophenyl)-1,3,4-oxadiazole, C18H18N4O5
  17. Crystal structure of (E)-N′-benzylidene-4-nitrobenzohydrazide – methanol (1/1), C15H15N3O4
  18. The crystal structure of 3-(2-bromophenyl)-1,5-di-p-tolylpentane-1,5-dione, C25H23BrO2
  19. Crystal structure of catena-poly[(μ 2-4,4′-bipyridine-κ2 N:N′)-bis(4-bromobenzoato-κ1 O)zinc(II)], C24H16Br2N2O4Zn
  20. Crystal structure of 1,1′-(1,2-ethanediyl)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S)zinc(II), C20H14N6ZnS4
  21. Crystal structure of pentacarbonyl-(μ2-propane-1,3-dithiolato-κ4 S:S,S′:S′)-(diphenyl(o-tolyl)phosphine-κ1 P)diiron (Fe-Fe), C27H23Fe2O5PS2
  22. The crystal structure of the cocrystal 4-hydroxy-3,5-dimethoxybenzoic acid–pyrazine-2-carboxamide(1/1), C14H15N3O6
  23. The crystal structure of dichlorido-bis((RS)-2-(4-chlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)hexanenitrile-κ1 N)zinc(II), C30H34Cl4N8Zn
  24. Crystal structure of the cocrystal 2,4,6-triamino-1,3,5-triazine – 1H-isoindole-1,3(2H)-dione – methanol (1/1/1), C12H15N7O3
  25. The crystal structure of methyl 4-((3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)methyl) benzoate, C23H28O3
  26. Crystal structure of (poly[µ2-(1H-pyrazol-1-yl)methyl]-1H-benzotriazole-κ 2 N:N)-(nitrato-κ 2 O:O′) silver(I), C9H8AgN7O3
  27. Crystal structure of tetraaqua-bis[4-(1H-1,2,4-triazol-1-yl)benzoato-k1 N]cadmium(II), C18H20CdN6O8
  28. The crystal structure of diaqua-bis(pyrazolo[1,5-a]pyrimidine-3-carboxylato-κ2N,O)nickel(II) dihydrate, C14H16N6O8Ni
  29. Crystal structure of poly[μ2-aqua-aqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2 N:N′)-(μ2-4,4′-(1H-1,2,4-triazole-3,5-diyl)dibenzoato-κ2 O:O′)-(μ4-4,4′-(1H-1,2,4-triazole-3,5-diyl)dibenzoato-κ5 O,O′:O″:O′″:O′″)dicobalt(II)] – water – dimethylformamide (1/1/1) C44H43N11O12Co2
  30. Crystal structure of N-((Z)-amino(((E)-amino(phenylamino)methylene) amino)methylene)benzenaminium chloride – benzo[f]isoquinolino[3,4-b][1,8]naphthyridine – tetrahydrofurane (1/2/2), C60H54ClN11O2
  31. The crystal structure of Chrysosplenol D, C18H16O8
  32. Crystal structure of poly[deca aqua-bis(μ 4-2-(triazol-1-yl)-benzene-1,3,5-tricarboxylato)- bis(μ 5-2-(triazol-1-yl)-benzene-1,3-dicarboxylato-5-carboxyl acid) pentamanganese(II)] dihydrate, C44H42Mn5N12O36
  33. Synthesis and crystal structure of (E)-1-(4-(((E)-3-(tert-butyl)-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C20H24N2O2
  34. The crystal structure of 4,4′-dichloro-6,6′-dimethoxy-2,2′,3,3′,5,5′- hexanitroazobenzene, C14H6N8O14Cl2
  35. Crystal structure of N 2,N 4-dimesitylpentane-2,4-diamine, C23H34N2
  36. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ 6O6)potassium(2-methylphenylamino)ethyl-2-methylphenylamide ammoniate (1/3.5), [K(18-crown-6)](o-CH3C6H4)NH(CH2)2N(o-CH3C6H4) 3.5 NH3, C28H53.5KN5.5O6
  37. The crystal structure of N′,N″,2-tris((E)-5-chloro-2-hydroxybenzylidene)hydrazine-1-carbohydrazonhydrazide hydrochloride – methanol (1/3), C25H30Cl4N6O6
  38. Crystal structure of (E)-7-bromo-2-(3,5-dimethoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C19H17BrO3
  39. Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)-4-hydroxybenzohydrazide, C15H13ClN2O3
  40. {2-(((2-aminoethyl)imino)methyl)-6-bromophenolato-κ3 N,N′,O}iron(III) nitrate, C18H20Br2FeN5O5
  41. Crystal structure of 2-(tert-pentyl)anthracene-9,10-dione, C19H18O2
  42. Crystal structure of 5,5′-(1,4-phenylene)bis(1H-imidazol-3-ium) bis(2-(2-(carboxymethyl)phenyl)acetate), C32H30N4O8
  43. Crystal structure of N 2,N 6-bis(2-(((E)-naphthalen-1-ylmethylene)amino)phenyl)pyridine-2,6-dicarboxamide, C41H29N5O2
  44. The crystal structure of 3-amino-1,2,4-triazolium 2,4,5-trinitroimidazolate, C5H5O6N9
  45. Hydrogen bonded dimers in the crystal structure of 2-chloro-N-(phenylcarbamoyl)nicotinamide, C26H20Cl2N6O4
  46. The crystal structure of 4,4′-bipyridine-5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one-water(1/2/2), C40H32N2O12
  47. Crystal structure of N,N'-bis(4-fluoro-salicylaldehyde)-3,6-dioxa-1,8-diaminooctane, C20H22F2N2O4
  48. Crystal structure of 3-(1,3-dinitropropan-2-yl)-4H-chromen-4-one, C12H10N2O6
  49. The crystal structure of (4-(2-bromoethoxy)-phenyl)(phenyl)methanone, C15H13BrO2
  50. Crystal structure of (E)-7-bromo-2-(4-methoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C18H15BrO2
  51. Crystal structure of dichlorido-tetrakis((E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ 1 N)cadmium(II), C60H68O4N12Cl10Cd
  52. Crystal structure of diaqua-diphenanthroline-κ2 N,N′-bis(μ2-2-carboxy-3,4,5,6-tetrafluorobenzoato-κ2 O:O′)-bis(μ2-tetrafluorophthalato-κ3 O,O′:O′)didysprosium(III) – phenanthroline (1/2), C80H38Dy2F16N8O18
  53. Crystal structure of bis(μ2-2-oxido-2-phenylacetato-κ3 O,O′:O′)-bis(N-oxido-benzamide-κ2 O,O′)-bis(propan-2-olato-κ1 O)dititanium(IV), C36H38N2O12Ti2
  54. Crystal structure of poly[diaqua-(μ2-1H-benzo[d][1,2,3]triazole-5-carboxylato-κ2 O:O′)(μ2-oxalato-κ4O,O:O″,O′″)europium(III)] monohydrate, C9H10N3O9Eu
  55. Crystal structure of bis((N-methyl-2-oxyethyl)amine)-bis(μ 2-N,N,N-tris(2-oxoethyl)amine)-bis(isopropoxy)-bis(μ 3-oxo)tetratitanium(IV)– isopropanol (1/2), C34H76N4O16Ti4
  56. Synthesis and crystal structure of ethyl 4-((4-iodobenzyl)amino)benzoate, C16H16INO2
  57. Crystal structure of (Z)-2-(tert-butyl)-5-((5-(tert- butyl)-2H-pyrrol-2-ylidene)(mesityl)methyl)-1H-pyrrole, C26H34N2
  58. Crystal structure of dimethylammonium poly[μ4-1,1′-(1,4- phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato-κ6 N,O:O′:N′,O″:O‴) manganese(II)], C22H26MnN6O8
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