Home Crystal structure of the cocrystal 2,4,6-triamino-1,3,5-triazine – 1H-isoindole-1,3(2H)-dione – methanol (1/1/1), C12H15N7O3
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Crystal structure of the cocrystal 2,4,6-triamino-1,3,5-triazine – 1H-isoindole-1,3(2H)-dione – methanol (1/1/1), C12H15N7O3

  • Madeline Christabel , Ruixue Zhou , Tianhao Yan , Haifei Zhang , Lifeng Ding and Ruiyao Wang ORCID logo EMAIL logo
Published/Copyright: July 12, 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

C12H15N7O3, P21/c (no. 14), a = 7.1782(3) Å, b = 16.6800(6) Å, c = 12.1070(5) Å, β = 92.030(2)°, V = 1448.69(10) Å3, Z = 4, Rgt (F) = 0.0449, wRref (F 2) = 0.1220, T = 296(2) K.

CCDC no.: 2182446

The molecular structure is shown in the figure (symmetry code i) −x + 1, y − 0.5, −z + 1.5; ii) −x + 1, y − 0.5, −z + 0.5; iii) x, −y + 1.5, z + 0.5; iv) −x + 1, y + 0.5, −z + 1.5; v) −x + 1, y + 0.5, −z + 0.5; vi) x, −y + 1.5, z − 0.5). 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: 0.20 × 0.20 × 0.20 mm
Wavelength: Cu Kα radiation (1.54178 Å)
μ: 0.89 mm−1
Diffractometer, scan mode: Bruker APEX3, φ and ω
θ max, completeness: 72.2°, 98%
N(hkl)measured, N(hkl)unique, R int: 12,956, 2788, 0.044
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2451
N(param)refined: 215
Programs: Bruker [1], Shelx [2, 3]
Table 2:

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

Atom x y z U iso*/U eq
O1 0.77763 (18) 0.48446 (7) 0.63688 (9) 0.0495 (3)
O2 0.73763 (17) 0.47187 (7) 0.26140 (9) 0.0472 (3)
N1 0.48553 (16) 0.76466 (7) 0.54272 (9) 0.0316 (3)
N2 0.48105 (17) 0.76418 (7) 0.34500 (9) 0.0347 (3)
N3 0.57738 (16) 0.64749 (7) 0.44564 (9) 0.0308 (3)
N4 0.58375 (17) 0.65188 (7) 0.63506 (9) 0.0359 (3)
H4A 0.565381 0.676383 0.696222 0.043*
H4B 0.624555 0.603403 0.635834 0.043*
N5 0.3781 (2) 0.87190 (8) 0.44225 (11) 0.0452 (4)
H5B 0.357019 0.895889 0.503428 0.054*
H5C 0.353090 0.895498 0.380335 0.054*
N6 0.5735 (2) 0.65050 (8) 0.25636 (10) 0.0473 (4)
H6B 0.613390 0.601880 0.257049 0.057*
H6C 0.553089 0.674837 0.194484 0.057*
N7 0.74011 (18) 0.49566 (8) 0.44844 (10) 0.0378 (3)
H7N 0.685 (3) 0.5476 (14) 0.4445 (17) 0.062 (6)*
C1 0.54889 (17) 0.68916 (8) 0.53879 (10) 0.0280 (3)
C2 0.44947 (19) 0.79830 (8) 0.44339 (11) 0.0313 (3)
C3 0.54331 (19) 0.68818 (8) 0.35128 (11) 0.0313 (3)
C4 0.87601 (19) 0.37945 (9) 0.51090 (12) 0.0364 (3)
C5 0.9523 (2) 0.31777 (10) 0.57374 (16) 0.0479 (4)
H5A 0.961700 0.320866 0.650429 0.057*
C6 1.0140 (2) 0.25114 (11) 0.51753 (19) 0.0561 (5)
H6A 1.066654 0.208632 0.557333 0.067*
C7 0.9991 (3) 0.24635 (11) 0.40369 (19) 0.0578 (5)
H7A 1.040814 0.200497 0.368521 0.069*
C8 0.9231 (2) 0.30867 (10) 0.34058 (16) 0.0490 (4)
H8A 0.913054 0.305583 0.263902 0.059*
C9 0.8635 (2) 0.37513 (9) 0.39665 (13) 0.0367 (3)
C10 0.7951 (2) 0.45710 (9) 0.54442 (12) 0.0360 (3)
C11 0.7750 (2) 0.45069 (9) 0.35583 (12) 0.0359 (3)
O1H 0.7746 (4) 0.46085 (12) 0.87128 (14) 0.1113 (8)
H1H 0.764 (5) 0.457 (2) 0.797 (4) 0.134*
C12 0.8271 (4) 0.53823 (16) 0.8936 (2) 0.0783 (7)
H12A 0.811 (5) 0.549 (2) 0.973 (3) 0.117*
H12B 0.752 (5) 0.579 (2) 0.850 (3) 0.117*
H12C 0.965 (5) 0.5445 (19) 0.883 (3) 0.117*

Source of material

2,4,6-Triamino-1,3,5-triazine (melamine) mono(dimethyl sulfoxide) solvate (MA-DMSO) was prepared by following the literature procedures [4]. MA-DMSO (25 mg, 0.198 mmol) was dissolved in methanol (12 mL) under reflux at 70 °C under N2 atmosphere to obtain a clear solution. To 4.0 mL of the solution, 29.2 mg (0.198 mmol) of 1H-isoindole-1,3(2H)-dione (phthalimide) was added. The mixture was kept at 50 °C to get a clear solution and was then cooled down naturally. Crystals of the title compound suitable for single crystal analysis were obtained in 2–3 days, with a yield of 12.5 mg or 50%.

Experimental details

A crystal of a size 0.20 × 0.20 × 0.20 mm was mounted on a glass fiber with expoxy glue. Data collection was performed on a Bruker D8 VENTURE Photon II diffractometer at room temperature, operating at 50 kV and 30 mA. Data were processed on a PC using the Bruker AXS Crystal Structure Analysis Package [1]. Data collection: Bruker APEX3; cell refinement: Bruker SAINT; Data reduction: Bruker SAINT; Structure solution: Shelxt 2014/5 [2]; Structure refinement: Shelxl-2018/3 [3]; Molecular graphics: Bruker Shelxtl [2]; Publication materials: Bruker Shelxtl [2].

The H-atoms on N7 and O1H were located from the difference-Fourier maps. All other H-atoms were placed geometrically and refined using a riding model with common isotropic displacement factors U iso(H) = 1.2 U eq (parent C-atom).

Comment

The development of multipoint hydrogen bonding motifs that form complexes or cocrystals with high stability and selectivity is important both for the understanding of biological processes and in the design of new materials [5]. In the study of organic semiconductors, the key materials of today’s organic electronics, hydrogen bonding have received surprisingly limited, but quickly growing attentions [6, 7]. Efficient charge transport in hydrogen-bonded materials has been realized in organic field-effect transistor (OFET) devices, where the organic complex or cocrystal serves as an active layer across extraordinary charge pathways, ensuring the efficient transport of induced charges [8], [9], [10], [11]. Naphthalenetetracarboxydiimide and its derivatives (NDIs) and related arylenetetracarboxydiimides are among the most promising candidates of next generation n-type organic semiconductors, with their electronic properties being easily tailored through π- and/or N-substitutions [12], [13], [14]. For examples, not only they show record-high electron mobilities in organic field electric transistors (OFETs), but also they are only second to fullerene derivatives when used in OPV as the acceptor. Meanwhile, the electronic properties of NDIs can be tuned through strong H-bonding interactions [15, 16].

With an Acceptor–Donor–Acceptor (ADA) structure, naphthalenetetracarboxydiimide (NDI) can triply hydrogen-bond to a compound with a complimentary structure, i.e. Donor–Acceptor–Donor (DAD) structure, such as 2,4-diaminopyridine or 2,4,6-triamino-1,3,5-triazine (melamine). However, since the structure of NDI is quite rigid, it has limited solubility in most of the solvents, which makes co-crystal production in solution very challenging. We therefore use 1H-isoindole-1,3(2H)-dione (phthalimide) as a model compound to study its co-crystallization reaction with melamine and the ADA…DAD triply hydrogen bonding. It is worth noting that, by reacting phthalimide (PI) and melamine (MA) via a gaseous phase reaction, a co-crystal compound, (MA)(PI)3 had been obtained [17].

The asymmetric unit contains one 2,4,6-triamino-1,3,5-triazine molecule (melamine: MA), one 1H-isoindole-1,3(2H)-dione molecule and one methanol solvent molecule (see the figure). All moieties are connected by hydrogen bonds to form the title cocrystal. The structure demonstrates a polymeric feature with each MA hydrogen-bonded to two neighboring MA molecules, two isoindoles and two methanol molecules. All bond lengths are in the expected ranges.

Corresponding author: Ruiyao Wang, Wisdom Lake Academy of Pharmacy, Xi’an Jiaotong-Liverpool University, 111 Ren’ai Road, Suzhou, Jiangsu 215123, P.R. China, E-mail:

Funding source: Key Program Special Fund of XJTLU

Award Identifier / Grant number: Research Project No. KSF-E-06

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

  2. Research funding: This work is supported by Key Program Special Fund of XJTLU (Research Project No. KSF-E-06).

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

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Received: 2022-05-20
Accepted: 2022-06-08
Published Online: 2022-07-12
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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  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-2022-0261
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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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