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Crystal structure of (S)-(+)-1-cyclohexylethylaminium chloride, C8H18NCl

  • Ann-Kathrin Scherer and Walter Frank ORCID logo EMAIL logo
Published/Copyright: April 29, 2020
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 235 Issue 4

Abstract

C8H18NCl, orthorhombic, P212121 (no. 19), a = 5.5244(3) Å, b = 11.0915(6) Å, c = 16.0339(12) Å, V = 982.46(11) Å3, Z = 4, Rgt(F) = 0.0295, wRref(F2) = 0.0785, T = 233(2) K.

CCDC no.: 1996962

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 needle
Size:0.90 × 0.30 × 0.22 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.33 mm−1
Diffractometer, scan mode:STOE IPDS 2T, ω
θmax, completeness:27.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:17396, 2248, 0.130
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2242
N(param)refined:104
Programs:SHELX [1], [2], Diamond [3]
Table 2:

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

AtomxyzUiso*/Ueq
Cl10.09050(8)0.13794(4)0.90935(3)0.04724(14)
N10.5898(3)0.27635(16)0.90315(9)0.0444(3)
H10.591(6)0.306(3)0.9595(19)0.083(9)*
H20.718(5)0.233(2)0.8945(15)0.051(6)*
H30.454(5)0.234(2)0.8988(16)0.060(7)*
C10.5740(3)0.37912(16)0.84298(10)0.0419(4)
H110.4304570.4278850.8581320.050*
C20.7976(4)0.4579(2)0.85491(14)0.0553(5)
H210.9421170.4097220.8465000.083*
H220.7981340.4907130.9109960.083*
H230.7949140.5234080.8148350.083*
C30.5348(3)0.33088(15)0.75430(11)0.0386(4)
H310.4033870.2703680.7574150.046*
C40.7574(4)0.26687(19)0.71782(11)0.0462(4)
H410.8926370.3238190.7144090.055*
H420.8054690.2006270.7547160.055*
C50.7024(4)0.21738(19)0.63133(12)0.0511(5)
H510.8480550.1790460.6086370.061*
H520.5758790.1557610.6355390.061*
C60.6196(4)0.3160(2)0.57266(11)0.0521(4)
H610.5778080.2808030.5184930.063*
H620.7517470.3736280.5640260.063*
C70.3998(4)0.3819(2)0.60811(13)0.0585(5)
H710.3572070.4491870.5713260.070*
H720.2616020.3265320.6099720.070*
C80.4496(4)0.42975(18)0.69545(12)0.0487(4)
H810.5735960.4927820.6923810.058*
H820.3015580.4662010.7177750.058*

Source of material

For the synthesis of (S)-(+)-1-cyclohexylethylaminium chloride 0.057 g (0.45 mmol) (S)-(+)-1-cyclohexylethylamine (Sigma-Aldrich) were mixed with 2 mL concentrated hydrochloric acid and 1 mL methanol. Colourless crystals (m.p. 521 K) suitable for X-ray crystal structure determination grew in the course of evaporating this solution to dryness under isothermal conditions (T = 293 K). Note that the compound crystallizes acicular with a strong tendency of the needles to break into thinner segments. Raman spectra were measured with a Bruker MultiRAM spectrometer equipped with a Nd:YAG laser (1064 nm) and an InGaAs detector. Raman 4000-70 cm−1: ν(C—H): 3050 cm−1 (w); ν(N—H): 2972 cm−1 (m); ν(C—H): 2928 cm−1 (vs), 2860 cm−1 (s); δas(C—H): 1444 cm−1 (m). IR spectroscopic data were obtained with a Perkin-Elmer Spektrum Two FT-IR spectrometer equipped with a LiTaO3 detector and universal ATR equipment. IR 4000-350 cm−1: ν(N—H): 2969 cm−1 (m); ν(C—H): 2924 cm−1 (vs), 2883 cm−1 (s), 2854 cm−1 (s), δ(N—H): 1606 cm−1 (m), 1518 cm−1 (m), δ(C—H): 1455 cm−1 (w), 1395 cm−1 (w). The band assignments are based on [4]. A CHN analysis was performed with a Elementar Analysensysteme vario Micro CUBE. EA C8H18NCl (163.688 g/mol): C 58.42, H 10.98, N 8.51; calc. C 58.70, H 11.08, N 8.56.

Experimental details

Positions of the H atoms bound to N1 and the majority of the hydrogen atoms bound to carbon atoms were identified by difference-Fourier synthesis. Coordinates and isotropic displacement parameters of the N-bonded H atoms were refined. For the C-bonded hydrogen atoms in the refinement a riding model was applied using idealized C—H bond lengths (0.97–0.99 Å) and H—C—H and C—C—H angles. In addition, the H atoms of the CH3-group were allowed to rotate around the adjacent C—C bond. The Uiso(C) values were set to 1.5Ueq(Cmethyl) and 1.2Ueq(Cmethylene and Cmethine). Absolute structure parameters were refined to 0.01(2) (Flack [5]) and 0.002(17) (Hooft [6]).

Comment

Enantiomers do not differ in their physical and chemical properties, but could differ in their physiological mode of action [7]. Therefore crystal structures of chiral amines or hydrochlorides thereof are almost exclusively related to investigations prior to pharmacological use. However, enantiomeric pure chiral amines or the related aminium ions may also serve as chiral building blocks for the construction of chiral supramolecular hydrogen-bonded networks in crystal engineering. Surprisingly, only very few crystal structures of carbon-based chiral primary amine hydrochlorides [R*–NH3]Cl are known so far, namely (S)-(–)-1-(4-methylphenyl)ethylammonium chloride [8], (S)-α-methylbenzylammonium chloride [9] and rimantadine hydrochloride [10]. Herein we present the crystal structure of the ‘chiral salt’ (S)-(+)-1-cyclohexylethylaminium chloride that exhibits a ladder-shaped hydrogen-bonded double chain combined with a ‘ladder in the tube’ structure motif based on the surrounding organic substituents.

The title compound crystallizes in the noncentrosymmetric space group P212121. The absolute structure is given by synthesis based on the corresponding amine, (S)-(+)-1-cyclohexylethylamine. The asymmetric unit of the crystal structure is defined by one (S)-(+)-1-cyclohexylethylaminium cation and one chloride anion. In the protonated amine moiety the bond lengths N1—C1 1.496(2) Å, C1—C2 1.526(3) Å, and C1—C3 1.535(2) Å as well as the angles at C1 are as expected [11]. The cyclohexyl group of the cation is present in the energetically most favourable conformation, the chair conformation [12]. The C—C bonds in the group have bond lengths of 1.514(3) Å to 1.536(3) Å with an average length of 1.524(3) Å, which is close to the reference value of 1.535(16) Å for C(sp3)–C(sp3) bonds in cyclohexyl groups [11]. In correspondence with the values given by Bastiansen et al. (gas phase ED of C6H12, [13]) and Kahn et al. (crystal structure analysis of C6H12-II [14]), the C—C—C bond angles in the six-membered ring vary from 110.17(15)° to 112.02(16)°, averaging to 111.10(16)° ([13]: 111.4°; [14]: 111.34°). The torsion angles in the cyclohexyl group range from 54.6(3)° to 57.4(2)° with an average value of 55.8(2)°, which is in good agreement with the calculated value of 55.7° [15]. Taking a closer look at the cation’s structure, it is obvious that C5—C6 is shorter and C3—C4 is longer than the average bond length in the cyclohexyl moiety. This is the only feature that might be attributed to the asymmetry of the chiral ethylaminium ‘substituent’ in equatorial postion. However, the difference is at the border of significance and the torsion angles C1—C3—C4—C5 [177.85(15)°] and C1—C3—C8—C7 [177.56(16)°] do not seem to be different, in both cases indicating a nearly staggered conformation. The NH3 group of the cation is engaged in N—H⋯Cl type hydrogen bonds to the neighbouring Cl− ions and each anion serves as an acceptor for two further hydrogen bonds. The N⋯Cl distances range from 3.1529(16) to 3.1650(17) Å and the hydrogen bond angles from 163(2) to 176(3)°. According to the bond valence method [16] these hydrogen bonds have to be characterized as moderately strong. As shown in the upper part of the figure, altogether the hydrogen bonds form a double-chain hydrogen bond system propagating along the a axis of the unit cell that is similar to the system found in (S)-(–)-1-(4-methylphenyl) ethylammonium chloride [8]. Note the graph set symbols [17] of the two hydrogen bond motifs defining this ladder-like structure. Projected along the chain propagation direction the lower part of the figure shows a packing diagram indicating the arrangement of the double-chains (blue) according to a moderately distorted hexagonal pattern. Around each of the double-chains a closed surrounding of organyl groups can be recognized that reminds of a tube (red). Each organyl group is part of three neighbouring tubes, giving a pattern of interpenetrating tubular ‘organic’ sections visualized by the different red areas in the figure. We suppose that this ‘ladder in the tube’-structure with its tightly interlocking organic groups is responsible for the unexpected high thermal stability (m. p. 521 K) in comparison to other classes of organylammonium chlorides.

Acknowledgements

We thank E. Hammes and P. Roloff for technical support.

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Received: 2020-03-04
Accepted: 2020-04-15
Published Online: 2020-04-29
Published in Print: 2020-06-25

©2020 Ann-Kathrin Scherer et al., published by De Gruyter, Berlin/Boston

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

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  62. Crystal structure and anti-inflammatory activity of (3E,5E)-3,5-bis(4-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)piperidin-4-one-dichloromethane (1/1), C26H20Cl2F3NO3S
  63. Crystal structure of (S)-(+)-1-cyclohexylethylaminium chloride, C8H18NCl
  64. The crystal structure of tris(nitrato-κ2O,O′)-bis(4,4,5,5-tetramethyl-2-(o-pyridyl)imidazoline-1-oxyl 3-oxide-κ2N,O)yttrium(III), C24H32N9O13Y
  65. Hydrogen bonding versus packing effects in the crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetraiodidozincate(II), C10H16I4ZnN2
  66. Dimerization of 2-[(2-((2-aminophenyl)thio)phenyl)amino]-cyclohepta-2,4,6-trien-1-one through hydrogen bonding, C19H16N2OS
  67. Crystal structure of 1-(4-chloro-phenyl)-7-ethoxyl-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, C18H12ClF2NO4
  68. Crystal structure of 7-ethoxy-6,8-difluoro-4-oxo-1-pyridin-2-ylmethyl-1,4-dihydro-quinoline-3-carboxylic acid, C18H14F2N2O4
  69. Crystal structure of octahydro-7aR,8′R-dimethylspiro[isobenzofuran-4(1H), 4′ (3′H)-[1H-7,9a]methanocyclohepta[c]pyran]-1′,3, 9′ (3aH,4′aH)-trione, C20H26O5
  70. Crystal structure of bis(5-ethoxy-2-(((1-hydroxy-2-methyl-3-oxidopropan-2-yl)imino)methyl)phenolato-κ3N,O,O’)manganese(IV) – methanol (1/1), C27H38MnN2O9
  71. Crystal structure of 8a,8a′′-oxybis(8aH-8,9-dioxa-3a1λ4-aza-8aλ4-borabenzo[fg]tetracene), C34H22B2N2O5
  72. Crystal structure of bromido-triphenyl-(triphenylarsine oxide-κO)tin(IV), C36H30AsBrOSn
  73. Crystal structure of catena-poly[chlorido-(μ2-formato-κ2O:O′)-(1,10-phenathroline-κ2N,N′)copper(II)], C26H18Cl2Cu2N4O4
  74. The crystal structure of poly[(μ10-5-carboxyisophthalato-κ10O)disodium], C9H4Na2O6
  75. The crystal structure of 3,5-difluoroisonicotinic acid, C6H3F2NO2
  76. The crystal structure of ethyl-1-(N-(adamantan-1-yl)-carbamothioyl)piperidine-4-carboxylate, C19H30N2O2S
  77. Crystal structure of 5-methyl-3-phenyl-1-tosyl-1,2,3,4-tetrahydropyridine, C19H21NO2S
  78. Crystal structure of bis((3-chlorosalicylidene)-ethylenediaminato-κ4N,N′,O,O′)nickel (II), C16H12Cl2NiN2O2
  79. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-4-hydroxybenzohydrazide — dihydrofuran-2(3H)-one (1/1), C18H17ClN2O5
  80. Crystal structure of bis((3-bromosalicylidene)-ethylenediaminato-κ4N,N′,O,O′) nickel (II), C16H12Br2NiN2O2
  81. Crystal structure of trimethylsulfoxonium tetrachloridocobaltate(II) [(CH3)3SO]2CoCl4
https://doi.org/10.1515/ncrs-2020-0121
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Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of bis [1-(phenylsulfonyl)-2-(1-(pyrazin-2-yl)ethylidene)hydrazin-1-ido-κ3N,N′,O]cobalt(II), C24H22N8O4S2Co
  3. The crystal structure of 1,3-bis(4-(methoxycarbonyl)benzyl)-2-methyl-1H-benzo[d]imidazol-3-ium bromide, C26H25BrN2O4
  4. Crystal structure of {tris((1H-benzo[d]imidazol-2-yl)methyl)amine-κ4N,N′,N′′,N′′′}-(nitrito-κ2O,O′)nickel(II) perchlorate – ethanol (1/1), C26H27ClN8NiO7
  5. Crystal structure of catena-poly[aqua[(μ2-4,5-dicarboxylato-2-(2-carboxylatophenyl)imidazol-1-ido-κ4N,O,O′:N′)](μ2-4,4′-bipyridine-κ2N:N′)dicopper(II)], C22H14Cu2N4O7
  6. Crystal structure of chlorido-tris(4-methylbenzyl-κC)-(triphenylarsine oxide-κO)tin(IV), C42H42AsClOSn
  7. The crystal structure of 4,4′-bipyridinium bis(3-carboxy-2-nitrobenzoate) tetrahydrate, C13H13N2O8
  8. Crystal structure of 1-(3-chlorophenyl)-4-(4-(((2,3-dihydro-1H-inden-5-yl)oxy)methyl)phenethyl)piperazine, C28H31ClN2O
  9. Crystal structure of catena-poly[diaqua-bis(μ2-5,5′-(1H-imidazole-4,5-diyl)bis(tetrazol-2-ido)-κ4N,N′:N′′,N′′′)magnesium], C10H8N20O2Mg
  10. The crystal structure of (E)-2-((2-hydroxy-4-ethoxybenzylidene)amino)-2-methylpropane-1,3-diol monohydrate, C13H21NO5
  11. Crystal structure of catena-poly[diaqua-(μ2-bipyridine-κ2N:N′)-bis(3,5-dichloroisonicotinato-κO)cadmium(II)] dihydrate, C22H20CdCl4N4O8
  12. The crystal structure of 4-(4-chlorophenyl)cyclohexane-1-carboxylic acid, C13H15ClO2
  13. Redetermination of the crystal structure of yttrium(III) trinitrate(V) pentahydrate, Y(NO3)3 ⋅ 5 H2O, H10N3O14Y
  14. Crystal structure of catena-poly[di-μ2-chlorido-1,10-phenanthroline-κ2N,N′-cadmium(II)], C12H8Cl2CdN2
  15. Crystal structure of 4-((2-methyl-6-(trifluoromethyl)pyrimidin-4-yl)oxy)benzoic acid, C13H9F3N2O3
  16. Crystal structure of 3-acetyl-4-hydroxybenzoic acid, C18H16O8
  17. Crystal structure of bis(N,2-bis(4-ethoxybenzylidene)hydrazine-1-carbohydrazonothioato-κ2N,S)nickel(II) — N,N-dimethylformamide (1/2), C44H56N10S2O6Ni
  18. The crystal structure of 5-chloro-4,6-dimethoxypyrimidin-2-amine, C6H8ClN3O2
  19. Crystal structure of poly[aqua-(μ4-benzene-1,2,4,5-tetracarboxylato-κ4O,O′,O′′,O′′′)bis(μ2-1-(4-(1H-imidazol-1-yl)benzyl)-1H-1,2,4-triazole-κ2N:N)dinickel(II)], NiC17H14N5O5
  20. Crystal structure of poly[aqua(5-dimethylamino)naphthalene-1-sulfonato-κ2N:O)(μ2-4,4′-bipyridyl -κ2N:N′)silver(I)], C44H44Ag2N6O8S2
  21. Crystal structure of 1-[3-(trifluoromethyl)cinnamoyl]-3-(pyridin-2-yl-κN)pyrazole-κ2N-bis(2-phenylpyridinato-k2C,N)iridium(III) hexafluorophosphate complex, [C40H28F3IrN5O]PF6
  22. Crystal structure of catena-poly[aqua(μ6-piperazine-1,4-bisethanesulfonato-κ6N:N′:O:O′:O′′:O′′′)(μ2-pyrazinyl-κ2N:N′)disilver(I)sesquihydrate], C12H30Ag2N4O11S2
  23. Crystal structure of (E)-1-(2-nitrophenyl)-N-(o-tolyl)methanimine, C14H12N2O2
  24. Crystal structure of 4′-amino-3′,5′-diisopropyl-(1,1′-biphenyl)-4-carbonitrile, C19H22N2
  25. The crystal structure of poly[bis(N,N-dimethylformamide-κ1O)-tetrakis(μ2-cyanido-κ2C:N)dinickel(II)], C10H14N6O2Ni2
  26. Crystal structure of rac-trans-N,N′-bis(3-bromo-5-chlorosalicylidene)-1,2-cyclohexanediamine, C20H18Br2Cl2N2O2
  27. Crystal structure of rac-trans-N,N′-bis(3,5-dibromosalicylidene)-1,2-cyclohexanediamine, C20H18Br4N2O2
  28. The crystal structure of (dichromato-κ2O,O′)bis(1,10-phenanthroline-κ2N,N′)nickel(II), C12H16N4O7Cr2Ni
  29. The crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetrachloridozincate(II) monohydrate, C10H18Cl4ZnN2O
  30. Crystal structure of bis(μ2-azido-k2N,N)-bis(2-amino-1-(N-(3-bromosalicylaldiminato))ethane)-dicopper(II), C20H18Br4N2O2
  31. Crystal structure of (η6-1-methyl-4-isopropylbenzene)-[5-bromo-2-(2-pyridyl)phenyl-κ2C,N]-chloro-ruthenium(II), C21H21BrClNRu
  32. Crystal structure of N-(methyl(oxo)(1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-λ6-sulfanylidene)cyanamide, C10H10F3N3OS
  33. Crystal structure of 6,6′-((cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2-bromo-4-chlorophenolato-κ4N,N′,O,O′)nickel(II), C20H16Br2Cl2NiN2O2
  34. Redetermination of the crystal structure of catena-poly[aqua-(1,10-phenanthroline-κ2N,N′)-(μ2-tetraoxidomolybdato(VI)-κ2O:O′)manganese(II) monohydrate, C12H12N2O6MoMn
  35. The crystal structure tetrakis(μ2-o-chlorobenzoato-κ2O:O′)-bis(methanol-κ1O)dirhodium(II), C30H24Cl4O10Rh2
  36. Crystal structure of bis(2,3-diphenyltetrazolidine-5-thione-κ1S)-(nitrato-κ1O)-(nitrato-κ2O,O′)lead(II), C26H20N10O6S2Pb
  37. Crystal structure of bis(3-bromo-N-(1-(3-methylpyrazin-2-yl)ethylidene)benzohydrazonato-κ3O,N,N′)cadmium(II) hemihydrate, C28H25N8O2.5Br2Cd
  38. Crystal structure of catena-poly[tetrakis(μ2-trifluoroacetato-κ2O:O′)(μ2-2,5-dimethylpyrazine-κ2N,N′)dicopper(II)], C7H4CuF6NO4
  39. The crystal structure of catena-poly[bis[3-azoniapentane-1,5-diammonium][bis(μ4-oxo)-tetrakis(μ3-oxo)-heptakis(μ2-oxo)-tetradecaoxo-octa-molybdenum] dihydrate], (C8H36N6O29Mo8)n
  40. Crystal structure of tetraaqua-bis(2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-κO)-nickel(II)—diaqua-bis(2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-nickel(II), C28H24Cl12N4Ni2O18
  41. The crystal structure of bis(2-hydroxypyrimidinium) pentachloridobismuthate(III), (C4N2H5O)2BiCl5
  42. The crystal structure of catena-poly[(μ2-4,4′-dipyridine-κ2N,N′)-bis(3,5,6-trichloropyridine-2-oxyacetato-κO)-bis(ethanol-κO)nickel(II)], C28H26Cl6N4NiO8
  43. Crystal structure and anti-inflammatory activity of (3E,5E)-1-((4-chlorophenyl)sulfonyl)-3,5-bis(4-fluorobenzylidene)piperidin-4-one-dichloromethane (1/1), C26H20Cl3F2NO3S
  44. The crystal structure of 5-bromopicolinic acid monohydrate, C6H6BrNO3
  45. The crystal structure of 2-(3-(4-bromophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-8H-indeno[1,2-d]thiazole, C25H17BrFN3S
  46. The crystal structure of catena-poly[(μ2-2-((3-bromo-2-oxidobenzylidene)amino)acetato-κ4O,N,O′:O′′)-(dimethylformamide-κ1O)]zinc(II), C12H13N2O4BrZn
  47. Crystal structure of aqua-azido-κ1N-(6,6′-((propane-1,3-diylbis(azanylylidene))bis(methanylylidene))bis(3-bromophenolato)-κ4N,N′,O,O′iron(III), C17H16Br2FeN5O3
  48. The crystal structure of tris(1-ethylimidazole-κ1N)-(sulfato-κ2O,O′)vanadium(IV), C15H24N6O5SV
  49. Crystal structure of (E)-3-methoxy-N′-(1-(pyridin-2-yl)ethylidene)benzohydrazide, C15H15N3O2
  50. Crystal structure of dichloro-bis-(1-butyl-1H-benzo[d]imidazole)-nickel(II), C22H28Cl2N4Ni
  51. The crystal structure of 2-(2,3-dimethoxyphenyl)-3-hydroxy-4H-chromen-4-one, C17H14O5
  52. The crystal structure of 5-(2-(4-fluorophenyl)hydrazono)-4-methyl-2-((3-(5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazono)-2,5-dihydrothiazole dimethylformamide monosolvate, C30H25FN10S⋅C3H7NO
  53. The crystal structure of 1,8-bis(pyridin-4-ylethynyl)anthracene-1,2,4,5-tetrafluoro-3,6-diiodobenzene (2/1), C62H32F4I2N4
  54. The crystal structure of 3,6-di-tert-butyl-1,8-diiodo-9-methyl-9H-carbazole, C21H25I2N
  55. The crystal structure of 8-((4-chlorophenylamino)methylene)-6,10-dioxaspiro[4.5]decane-7,9-dione, C15H14ClNO4
  56. The crystal structure of catena-poly[oktaaqua-bis(μ2-4,4′-ethene-1,2-diyldipyridine-κ2N:N′)-(μ2-3,3′-(1-oxidodiazene-1,2-diyl)diphthalato-κ2O:O′)dicobalt(II)] dihydrate, C28H36N4O19Co2
  57. Crystal structure of (E)-1-(2-cyano-3-oxo-1-phenylprop-1-en-1-yl)-3,7-diphenylindolizine-6-carbonitrile, C31H19N3O
  58. Crystal structure of 1,1′-bis(diphenylphosphino)ferrocene-(1,1′-bis(diphenylphosphino)ferrocene-κ2P,P′)-(O-isobutyl sulfurodithioito-κ2S,S′)copper(I), C39H37CuFeOP2S2
  59. Crystal structure of poly[(5-bimethylamino-1-naphthalenesulfonato-κO)-(μ3-hexamethylenetetramino-κ3N:N′:N′′)silver(I)] dihydrate, C36H52Ag2N10O8S2
  60. Crystal structure of poly[μ2-diaqua-(μ2-2-amino-4,5-dicyano-κ2N:N′-imidazol-1-ide)sodium(I)], C5H6N5O2Na
  61. Crystal structure of (1,3-propanediamine-κ2N,N′)(N-(3-aminopropyl)-α-methyl aspartato-κ4N,N′,O,O′)cobalt(III) chloride, C11H24ClCoN4O4
  62. Crystal structure and anti-inflammatory activity of (3E,5E)-3,5-bis(4-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)piperidin-4-one-dichloromethane (1/1), C26H20Cl2F3NO3S
  63. Crystal structure of (S)-(+)-1-cyclohexylethylaminium chloride, C8H18NCl
  64. The crystal structure of tris(nitrato-κ2O,O′)-bis(4,4,5,5-tetramethyl-2-(o-pyridyl)imidazoline-1-oxyl 3-oxide-κ2N,O)yttrium(III), C24H32N9O13Y
  65. Hydrogen bonding versus packing effects in the crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetraiodidozincate(II), C10H16I4ZnN2
  66. Dimerization of 2-[(2-((2-aminophenyl)thio)phenyl)amino]-cyclohepta-2,4,6-trien-1-one through hydrogen bonding, C19H16N2OS
  67. Crystal structure of 1-(4-chloro-phenyl)-7-ethoxyl-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, C18H12ClF2NO4
  68. Crystal structure of 7-ethoxy-6,8-difluoro-4-oxo-1-pyridin-2-ylmethyl-1,4-dihydro-quinoline-3-carboxylic acid, C18H14F2N2O4
  69. Crystal structure of octahydro-7aR,8′R-dimethylspiro[isobenzofuran-4(1H), 4′ (3′H)-[1H-7,9a]methanocyclohepta[c]pyran]-1′,3, 9′ (3aH,4′aH)-trione, C20H26O5
  70. Crystal structure of bis(5-ethoxy-2-(((1-hydroxy-2-methyl-3-oxidopropan-2-yl)imino)methyl)phenolato-κ3N,O,O’)manganese(IV) – methanol (1/1), C27H38MnN2O9
  71. Crystal structure of 8a,8a′′-oxybis(8aH-8,9-dioxa-3a1λ4-aza-8aλ4-borabenzo[fg]tetracene), C34H22B2N2O5
  72. Crystal structure of bromido-triphenyl-(triphenylarsine oxide-κO)tin(IV), C36H30AsBrOSn
  73. Crystal structure of catena-poly[chlorido-(μ2-formato-κ2O:O′)-(1,10-phenathroline-κ2N,N′)copper(II)], C26H18Cl2Cu2N4O4
  74. The crystal structure of poly[(μ10-5-carboxyisophthalato-κ10O)disodium], C9H4Na2O6
  75. The crystal structure of 3,5-difluoroisonicotinic acid, C6H3F2NO2
  76. The crystal structure of ethyl-1-(N-(adamantan-1-yl)-carbamothioyl)piperidine-4-carboxylate, C19H30N2O2S
  77. Crystal structure of 5-methyl-3-phenyl-1-tosyl-1,2,3,4-tetrahydropyridine, C19H21NO2S
  78. Crystal structure of bis((3-chlorosalicylidene)-ethylenediaminato-κ4N,N′,O,O′)nickel (II), C16H12Cl2NiN2O2
  79. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-4-hydroxybenzohydrazide — dihydrofuran-2(3H)-one (1/1), C18H17ClN2O5
  80. Crystal structure of bis((3-bromosalicylidene)-ethylenediaminato-κ4N,N′,O,O′) nickel (II), C16H12Br2NiN2O2
  81. Crystal structure of trimethylsulfoxonium tetrachloridocobaltate(II) [(CH3)3SO]2CoCl4
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