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Crystal structure of 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile, C12H14N2

  • Yingfan Liu EMAIL logo and Mengfei Wang
Published/Copyright: August 15, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 5

Abstract

C12H14N2, monoclinic, P21/c (no. 14), a = 10.16290(10) Å, b = 8.25800(10) Å, c = 13.4328(2), β = 95.910(1)∘, V = 1121.36(2) Å3, Z = 4, R gt (F) = 0.0380, wR ref (F2) = 0.1126, T = 294 K.

CCDC no.: 1832141

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 (Figure 1).

Table 1:

Data collection and handling.

Crystal: Yellow block
Size: 0.60 × 0.45 × 0.42 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 0.51 mm−1
Diffractometer, scan mode: SuperNova, ω
θmax, completeness: 71.6°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 3671, 2139, 0.008
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 1960
N(param)refined: 131
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 Uiso*/Ueq
C1 0.95319 (14) 0.19810 (19) 0.58784 (16) 0.0886 (5)
H1A 0.937886 0.192964 0.516190 0.133*
H1B 0.950306 0.090838 0.615090 0.133*
H1C 1.038492 0.245051 0.606867 0.133*
C2 0.86581 (15) 0.3063 (2) 0.74244 (12) 0.0791 (4)
H2A 0.951900 0.348962 0.764107 0.119*
H2B 0.858505 0.198510 0.768022 0.119*
H2C 0.799428 0.373935 0.767007 0.119*
C3 0.84613 (10) 0.30248 (14) 0.62833 (10) 0.0564 (3)
C4 0.71067 (11) 0.23079 (14) 0.59265 (10) 0.0568 (3)
H4A 0.705277 0.213780 0.520899 0.068*
H4B 0.702398 0.126038 0.624083 0.068*
C5 0.59753 (10) 0.33623 (13) 0.61587 (7) 0.0468 (3)
C6 0.61680 (11) 0.50934 (13) 0.61440 (8) 0.0491 (3)
H6 0.545931 0.576941 0.623764 0.059*
C7 0.73334 (11) 0.57547 (13) 0.60001 (8) 0.0500 (3)
C8 0.85237 (11) 0.47402 (14) 0.58650 (10) 0.0579 (3)
H8A 0.930156 0.527686 0.619013 0.069*
H8B 0.862654 0.467315 0.515626 0.069*
C9 0.75105 (14) 0.75502 (15) 0.59533 (11) 0.0650 (4)
H9A 0.666870 0.807258 0.596729 0.097*
H9B 0.787733 0.783005 0.534557 0.097*
H9C 0.809902 0.790037 0.651709 0.097*
C10 0.47978 (10) 0.26966 (14) 0.63330 (8) 0.0499 (3)
C11 0.45798 (11) 0.09777 (15) 0.63106 (8) 0.0551 (3)
C12 0.36794 (11) 0.36560 (17) 0.65226 (9) 0.0592 (3)
N1 0.43880 (12) −0.03904 (15) 0.62874 (9) 0.0734 (4)
N2 0.27682 (12) 0.43866 (19) 0.66729 (10) 0.0820 (4)
Figure 1: A view of the molecule. Displacement ellipsoids are drawn at the 50 % probability level and H atoms are shown as small spheres of arbitrary radii.
Figure 1:

A view of the molecule. Displacement ellipsoids are drawn at the 50 % probability level and H atoms are shown as small spheres of arbitrary radii.

1 Source of material

The title compound, 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile, was synthesized according to the literatured methodology with slight modification [5, 6]. Ethanol is the better solvent for the condenstation between isophorone and malononitrile in contrast to toluene. Additionally, the condensation could be smoothly proceeded at lower temperature. To a 100 mL round bottom flask, isophorone 3.45 g (25 mmol) and malononitrile 1.65 g (25 mmol) were dissolved in anhydrous ethanol 50 mL. Then sodium acetate trihydrate (1 g, 12.5 mmol) was added. The mixture was heated to 80 °C and stirred for about 12 h. The reaction progress was monitored by TLC. Once the starting isophorone disappeared totally on TLC and the target spot formed regularly, the reaction mixture was cooled to room temperature. The solid sodium acetate trihydrate was removed by filtration. 25 mL Ethanol was removed in vacuum. The left mixture was stand still at −27 °C for overnight. The crystals were collected by filtration and washed carefully with cooled anhydrous ethanol. The analytical samples can be obtained by recrystallization one more time from ethanol. Crystals were obtained by slow evaporation of its solution in anhydrous ethanol within several days.

2 Experimental details

Hydrogen atoms attached to C atoms were placed geometrically and refined using a riding model approximation, with d (C–H) = 0.93 Å or 0.96 Å (–CH3, –CH2). Uiso(H) = 1.2 Ueq(C) for CH or Uiso(H) = 1.5 Ueq(C) for CH3 and CH2 groups [3].

3 Comment

2-(3,5,5–Trimethylcyclohex-2-en-1-ylidene)malononitrile was an important intermediate in the construction of chemical sensors and dye-sensitized solar cells [7], [8], [9], [10]. Due to the acidity of 3-position methyl, cabronyl-containing compounds can be condensed smoothly with this methyl. Based on the strong electron withdrawing power of malononitrile, it is easy to construct an intramoleular electron push-pull effect. Together with the asymmetrical π conjugation structure of the isophorone skelton, a significant fluorescence red-shifting occured. The emission peaks of these fluorescent derivatives generally extends to red region (640–680 nm) and saturated red-emitting devices were fabricated using these materias as dopants.

In the title crystal structure, the asymmetric unit contains one molecule. Most of the atoms are coplanar with the RMSD distance estimated to be 0.040 Å. Only C3, including the two bonded methyl grous (C1 and C2) is twisted out of this molecular plane with the distance of 0.6238 Å. The angel between the malononitrile group (N1/C11/C10/C12/N2) and plane (C4/C5/C6/C7/C8) is determined to be 1.523(1.5)°. The distances of C5–C10 and C6–C7 are 1.359 and 1.336 Å, respectively, which have the typical character of double bonds. The alternating single/double bond character demonstrates that the malononitrile group was conjugated with the isophorone. In addition, the cohesion of adjacent molecules depends on the intermolecular hydrogen bonds (C2–H2b⋯N2, C1–H1c⋯N2, C9–H9c⋯N2, C4–H4a⋯N1, C9–H9a⋯N1, C3–H4a⋯N1) [11]. The H⋯N distances range from 2.715 to 3.006 Å. The N⋯C contacts were determined to be about 3.568–3.913 Å, which are inside the interval of 3.0–4.0 Å, basing on a survey of over 100 structures. The C–H⋯N angles (from 140.2–171.9°) are also in agreement with the above mentioned survey [11, 12]. The hydrogen bonds analysis in solid and crystal structure is useful for depper understanding the solid emission behavior of fluorescent materials [13], [14], [15], [16], [17]. Configuration of the intermolecular hydrogen bonding in dye materials can be used to modify the excitate of dye molecules, and thus modify the emission efficiency. The stronger the intermolecular hydrogen bonds constructed, the more signficiant fluorescence quench will be.

The intermolecular interactions that stabilized the crystal lattice were mainly the C–H⋯N hydrogen bonds. In total, six hydrogens (H2C, H9A, H4A, H2B, H1C, and H9C) were involved. They connect the adjacent molecules in layers. In addition, no C–H⋯π interactions were established in the crystal lattice [18]. Interestingly, there exist weak π⋯π interactions between the double bond of C6–C7 and C5–C10, which assemble the adjacent molecules parallel-displaced to each other [19, 20]. It also plays an important role to the emission behavior of dye molecules. The emission enhancement or quenching of dye depends on the non-radiative energy transfer between excited molecules and the environment [21], [22], [23]. Owing to the various interactions existing in the crystal, the molecules were staggered layer by layer along the axis c, and H⋯N interactions promoted the cohesion of the crystal [24, 25]. Both the bond lengths and the angles are in the expected ranges [26, 27].

Corresponding author: Yingfan Liu, College of Material and Chemical Engineering, Zhengzhou University of Light Industry, Henan Provincial Key Lab of Surface and Interface Science, Zhengzhou, 450002, P.R. China, E-mail:

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

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

  3. Research funding: None declared.

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Supplementary Material

This article contains supplementary material (https://doi.org/10.1515/ncrs-2023-0316).

Received: 2023-07-08
Accepted: 2023-08-01
Published Online: 2023-08-15
Published in Print: 2023-10-26

© 2023 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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  46. Crystal structure of 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene-N,N′-bis(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-1,3,2-diazaborol-2-yl)-l2-germenediamine, C63H94B2GeN8
  47. The crystal structure of (bromido, chlorido)-tricarbonyl-(5,5′-dimethyl-2,2′-bipyridine)-rhenium(I), C15H12Br0.2Cl0.8N2O3Re1
  48. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-bis(propan-2-yl)-1H-pyrazol-4-amine, C26H36N6
  49. The crystal structure of poly[2-(4-carboxypyridin-3-yl)terephthalpoly[diaqua-(μ4-2-(6-carboxylatopyridin-3-yl)terephthalato-κ5O,N:O′:O″,O‴)]) cadmium(II)] dihydrate, C28H20Cd3N2O16
  50. Crystal structure of [tetraaqua-bis((3-carboxy-5-(pyridin-4-yl)benzoate-κ1N)cobalt(II)] tetrahydrate, C26H32CoN2O16
  51. Crystal structure of bis(μ2-azido-κ2N:N)-tetrakis(azido-κ1N)-tetrakis(1,10-phenanthroline-κ2N,N′)dibismuth(III), C48H32N26Bi2
  52. Crystal structure of (Z)-N-(4-(4-(4-((4,5,6-trimethoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)phenoxy)butoxy)phenyl)acetamide, C30H31NO8
  53. Crystal structure of poly[diaqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-bis(μ2-5-carboxybenzene-1,3-dicarboxylato-O,O′:O″)-aqua-di-zinc dihydrate solvate], C27H28N4O16Zn2
  54. Crystal structure of 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile, C12H14N2
  55. Crystal structure of chlorido-(5-nitro-2-phenylpyridine-κ2N,C)-[(methylsulfinyl)methane-κ1S]platinum(II), C13H13ClN2O3PtS
  56. The crystal structure of the co-crystal 1,4-dioxane–4,6-bis(nitroimino)-1,3,5-triazinan-2-one(2/1), C11H19N7O9
  57. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-dimethyl-1H-pyrazol-4-amine di-methanol solvate, C18H20N6·2(CH3OH)
  58. Crystal structure of catena-poly[bis(μ2-azido-k2N:N′)-(nitrato-K2N:N′)-bis(1,10-phenanthroline-K2N:N′)samarium(III)], C24H16N11O3Sm
  59. Crystal structure of (Z)-2-(4-((5-bromopentyl)oxy)benzylidene)-4,5,6-trimethoxybenzofuran-3(2H)-one, C23H25BrO6
  60. Crystal structure of bis(3,5-dimethyl-1H-pyrazol-4-ammonium) tetrafluoroterephthate, 2[C5H10N3][C8F4O4]
  61. Crystal structure of 2-amino-4-(2-fluoro-4-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  62. Crystal structure of 6-(pyridin-3-yl)-1,3,5-triazine-2,4-diamine-sebacic acid (2/1), C13H17N6O2
https://doi.org/10.1515/ncrs-2023-0316
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of (N-([1,1′:4′,1″-terphenyl]-4,4′-diethyl)-2-(bis(pyridin-2-ylmethyl)amino)acetamide-κ4N,N,N″, O)tri(nitrato-kO, O′) samarium(III) - methanol - acetonitrile (1/1/1), C40H39SmN8O14
  4. The crystal structure of 6,6′-(((2-(dimethylamino)ethyl)azanediyl)bis(methylene))bis(2-chloro-4-methyl phenolate-κ4N,N′,O,O′)-(pyridine-2,6-dicarboxylato-N,O,O′)-titanium(IV), C27H27Cl2N3O6Ti
  5. N′-[(1E)-(4–Fluorophenyl)methylidene]adamantane-1-carbohydrazide, C18H21FN2O
  6. Crystal structure of 4-bromo-3-nitro-1H-pyrazole-5-carboxylic acid monohydrate, C4H2N3BrO4·H2O
  7. Crystal structure of dipyridine-k1N-tris(2,2,6,6-tetramethyl-5-oxohept-3-en-3-olato-k2O,O′)dysprosium(III), DyC43H67O6N2
  8. Crystal structure of cyclo[tetraiodido-bis{μ2-1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-isopropyl-imidazol)-k2N:N}dicadmiun(II)], C26H30N10Cd2I4
  9. The crystal structure of tert-butyl (E)-3-(2-(benzylideneamino)phenyl)-1H-indole-1-carboxylate, C26H24N2O2
  10. The crystal structure of 4-(3-carboxy-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4- dihydroquinolin-7-yl)-2-methylpiperazin-1-ium 2,5-dihydroxybenzoate methanol solvate, C27H32FN3O9
  11. Crystal structure of (μ2-1-(4,4′-bipyridine-κ2N:N′)-bis[diaqua-(4-iodopyridine-2,6-dicarboxylato-κ3O,N,O′)–cobalt(II)], C24H20Co2I2N4O12
  12. The crystal structure of dimethyl 4,4′-(10,20-diphenylporphyrin-5,15-diyl)dibenzoate dichloromethane solvate, C49H36N4O4Cl2
  13. (E)-2-((E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-ylidene)hydrazine-1-carbothioamide C14H23N3S1
  14. The crystal structure of [1-(4-(trifluoromethyl)phenyl)-3,4-dihydroquinolin-2(1H)-one], C16H12F3NO
  15. Crystal structure of (E)-2-amino-N′-((3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene)benzohydrazide – dimethylformamide – water (1/1/2), C15H16N4O3·C3H7NO·2H2O
  16. Crystal structure of 3-(4-bromophenyl)-5-methyl-1H-pyrazole, C10H9BrN2
  17. Crystal structure of 1,10-phenanthrolinium bromide dihydrate, C12H9N2Br
  18. Crystal structure of N-(4′-chloro-[1,1′-biphenyl]-2-yl)formamide, C13H10ClNO
  19. The crystal structure of nitroterephthalic acid, C8H5NO6
  20. Crystal structure of (2-((4-bromo-2,6-dichlorophenyl)amino)phenyl) (morpholino)methanone, C17H15BrCl2N2O2
  21. Crystal structure of tetraaqua-bis(ethanol-κO)-tetrakis(μ2-trifluoroacetate-κ2O:O′)-bis(trifluoroacetate-κ2O)digadolinium(III) Gd2C16H20O18F18
  22. The crystal structure of dimethyl 4,4′-[10,20-bis(2,6-difluorophenyl)porphyrin-5,15-diyl]dibenzoate chloroform solvate, C50H32Cl6F4N4O4
  23. The crystal structure of N,N′-((nitroazanediyl)bis(methylene))diacetamide, C6H12O4N4
  24. The crystal structure of [bis(2,2′-bipyridine-6-carboxylato-κ3N,N,O)magnesium(II)]dihydrate, C22H18N4O6Mg
  25. Crystal structure of poly[diaqua-(bis(μ2-1,4-bis(imidazol-1-ylmethyl)benzene)-κ2N,N′] cobalt(II)-tetraqua-bis(1,4-bis(imidazol-1-ylmethyl)benzene)-κ1N)-cobalt(II) di(2,5-thiophenedicarboxylate) dihydrate, C68H76Co2N16O16S2
  26. Crystal structure of poly[chlorido-μ2-chlorido-(μ2-1-[(2-ethyl-4-methyl-1H-imidazol-1-yl)methyl]-1H-benzotriazole-κN:N’)cadmium(II)], C13H15CdN5Cl2
  27. The crystal structure of (4-hydroxybenzenesulfonate)-k1O-6,6′-((1E,1′E)- (ethane-1,2-diylbis(azaneylylidene))bis(methaneylylidene)) bis(2-methoxyphenol)-κ2N,N,μ2O,O,κ2O, O)-(methanol)-cobalt(II) sodium(I), C25H27CoN2NaO9S
  28. Crystal structure of (1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)(4-((2-methyl-6-(trifluoromethyl)pyrimidin-4-yl)amino)piperidin-1-yl)methanone, C17H18F6N6O
  29. Crystal structure of bis{[(cyclohexylimino)(phenylimino)-l5-(methyl)diethylazane-κ2N:N′]-(ethyl)-zinc(II)]}, C38H62N6Zn2
  30. Crystal structure of 2-[(4-bromobenzyl)thio]-5-(5-bromothiophen-2-yl)-1,3,4-oxadiazole, C13H8Br2N2OS2
  31. Crystal structure of 10-methoxy-7,11b,12,13-tetrahydro-6H-pyrazino [2′,3′:5,6]pyrazino[2,1-a]isoquinoline, C15H16N4O
  32. The crystal structure of 1-propyl-2-nitro-imidazole oxide, C6H9N3O3
  33. The crystal structure of 3-nitrobenzene-1,2-dicarboxylic acid–2-ethoxybenzamide (1/1), C17H16N2O8
  34. The structure of RUB-1, (C8H16N)6[B6Si48O108], a boron containing levyne-type zeolite, occluding N-methyl-quinuclidinium in the cage-like pores
  35. The crystal structure of diaqua-(naphthalene-4,5-dicarboxylate-1,8-dicarboxylic anhydride-κ1O)-(4′-(4-(1H-benzimidazolyl-1-yl)phenyl)-2,2′:6′,2″-terpyridine-κ3N,N′,N″)–manganese(II) dihydrate, C42H27MnN5O9·2H2O
  36. Crystal structure of 6,6′-((1E,1′E)-hydrazine-1,2-diylidenebis(methanylylidene))bis (3-(3-bromopropoxy)phenol), C20H22Br2N2O4
  37. The crystal structure of 3-(2-hydroxyphenyl)-4-phenyl-6-(p-tolyl)-2H-pyran-2-one, C24H18O3
  38. Crystal structure of bis(μ2-2-(1,5-dimethyl–3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino)methyl)phenolato-κ4O:O,N,O′)-(nitrato-κ2O,O′)dicobalt(II), C36H32Co2N8O4
  39. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α] phenanthren-3-one O-(4-fluorobenzoyl) oxime, C28H36FNO2
  40. The crystal structure of 4-aminiumbiphenyl benzenesulfonate, C18H17NO3S
  41. Synthesis and crystal structure of 1-(7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)-N,N-dimethylmethanaminiumnitrate, C18H17N3O9
  42. Crystal structure of N-(Ar)-N′-(Ar′)-formamidine, C14H12Br2N2O
  43. The crystal structure of 4-(2,4-dichlorophenyl)-2-(4-fluorophenyl)-5-methyl-1H-imidazole, C16H11Cl2FN2
  44. Crystal structure of 1-(4–chlorophenyl)-4-benzoyl-3-methyl-1H-pyrazol-5-ol, C17H13ClN2O2
  45. The crystal structure of 5-amino-1-methyl-4-nitroimidazole, C4H6O2N4
  46. Crystal structure of 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene-N,N′-bis(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-1,3,2-diazaborol-2-yl)-l2-germenediamine, C63H94B2GeN8
  47. The crystal structure of (bromido, chlorido)-tricarbonyl-(5,5′-dimethyl-2,2′-bipyridine)-rhenium(I), C15H12Br0.2Cl0.8N2O3Re1
  48. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-bis(propan-2-yl)-1H-pyrazol-4-amine, C26H36N6
  49. The crystal structure of poly[2-(4-carboxypyridin-3-yl)terephthalpoly[diaqua-(μ4-2-(6-carboxylatopyridin-3-yl)terephthalato-κ5O,N:O′:O″,O‴)]) cadmium(II)] dihydrate, C28H20Cd3N2O16
  50. Crystal structure of [tetraaqua-bis((3-carboxy-5-(pyridin-4-yl)benzoate-κ1N)cobalt(II)] tetrahydrate, C26H32CoN2O16
  51. Crystal structure of bis(μ2-azido-κ2N:N)-tetrakis(azido-κ1N)-tetrakis(1,10-phenanthroline-κ2N,N′)dibismuth(III), C48H32N26Bi2
  52. Crystal structure of (Z)-N-(4-(4-(4-((4,5,6-trimethoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)phenoxy)butoxy)phenyl)acetamide, C30H31NO8
  53. Crystal structure of poly[diaqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-bis(μ2-5-carboxybenzene-1,3-dicarboxylato-O,O′:O″)-aqua-di-zinc dihydrate solvate], C27H28N4O16Zn2
  54. Crystal structure of 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile, C12H14N2
  55. Crystal structure of chlorido-(5-nitro-2-phenylpyridine-κ2N,C)-[(methylsulfinyl)methane-κ1S]platinum(II), C13H13ClN2O3PtS
  56. The crystal structure of the co-crystal 1,4-dioxane–4,6-bis(nitroimino)-1,3,5-triazinan-2-one(2/1), C11H19N7O9
  57. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-dimethyl-1H-pyrazol-4-amine di-methanol solvate, C18H20N6·2(CH3OH)
  58. Crystal structure of catena-poly[bis(μ2-azido-k2N:N′)-(nitrato-K2N:N′)-bis(1,10-phenanthroline-K2N:N′)samarium(III)], C24H16N11O3Sm
  59. Crystal structure of (Z)-2-(4-((5-bromopentyl)oxy)benzylidene)-4,5,6-trimethoxybenzofuran-3(2H)-one, C23H25BrO6
  60. Crystal structure of bis(3,5-dimethyl-1H-pyrazol-4-ammonium) tetrafluoroterephthate, 2[C5H10N3][C8F4O4]
  61. Crystal structure of 2-amino-4-(2-fluoro-4-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  62. Crystal structure of 6-(pyridin-3-yl)-1,3,5-triazine-2,4-diamine-sebacic acid (2/1), C13H17N6O2
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