Home Physical Sciences Crystal structure of sodium morpholine-4-carbodithioate, (C5H12NNaO3S2)
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Crystal structure of sodium morpholine-4-carbodithioate, (C5H12NNaO3S2)

  • Nolwazi Solomane , Peter A. Ajibade and Bernard Omondi EMAIL logo
Published/Copyright: March 26, 2019
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 234 Issue 4

Abstract

C5H12NNaO3S2, monoclinic, P21/c (no. 14), a = 28.8222(3) Å, b = 5.6782(3) Å, c = 12.3810(9) Å, β = 102.074(2)°, V = 1987.43(17) Å3, Z = 8, Rgt(F) = 0.0269, wRref(F2) = 0.0591, T = 100(2) K.

CCDC no.: 1855486

The asymmetric unit of the title crystal structure is shown in the figure (The disorder in the morpholine moieties is amitted for clarity.). Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Source of material

The title compound was synthesized by dispersing (4.33 mL, 50 mmol) of morpholine into 20 mL of diethyl ether and stirred for 10 minutes. Followed by the addition of 20 mL of an ice cold methanolic solution of sodium hydroxide (2.00 g, 50 mmol) and stirred for 15 minutes at an ice-cold temperature. To this mixture, cold carbon disulfide (3 mL, 50 mmol) was added dropwise. The mixture was stirred for 4 h while maintaining an ice-cold temperature resulting in a formation of white precipitate which was collected by filtration. The product obtained was rinsed with diethyl ether and dried in a desiccator. The crystals of the title compound were formed after four days of extracting the filtrate with diethyl ether. White powder. Yield = 61%. m.p. 308.4−310.3 °C. 1H NMR D2O: δ = 3.77 (4H, t, N—CH2), 4.36 (4H, t, O—CH2). 13C NMR D2O: δ = 51.40 (N—CH2), 66.13 (O—CH2), 209.36 (C-SSNa). IR v(cm−1): 972 (C—S), 1108 (C=S), 1414 (C—N). MS (m/z): 162.0045 [M+].

Table 1:

Data collection and handling.

Crystal:Yellow block
Size:0.36 × 0.23 × 0.14 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.55 mm−1
Diffractometer, scan mode:Bruker SMART, φ and ω-scans
θmax, completeness:27.4°, >99%
N(hkl)measured, N(hkl)unique, Rint:31639, 4506, 0.024
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4308
N(param)refined:150
Programs:Bruker programs [1], SHELX [2], WinGX and ORTEP [3]
Table 2:

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

AtomxyzUiso*/Ueq
S10.55623(2)0.03105(6)0.78588(3)0.01240(8)
O10.45297(4)−0.09325(19)0.91778(9)0.0155(2)
S20.63255(2)0.23405(7)0.96360(3)0.01908(9)
S40.94367(2)−0.03262(6)1.23051(3)0.01196(8)
S30.86773(2)−0.24153(6)1.33344(3)0.01535(8)
Na10.49327(2)0.25887(10)0.91592(4)0.01334(12)
Na20.99301(2)0.24134(10)1.07727(4)0.01347(12)
O20.54519(4)0.5878(2)0.94798(9)0.0150(2)
O30.95269(4)0.59302(19)1.03569(9)0.0151(2)
O41.04453(4)−0.0892(2)1.09677(9)0.0155(2)
O1Aa0.71454(6)−0.3683(3)0.76431(14)0.0275(4)
C2Aa0.66508(7)−0.3968(4)0.72608(17)0.0224(4)
H2AAa0.651540−0.4733590.7843750.027*
H2ABa0.659231−0.5013200.6606380.027*
C1Aa0.64031(8)−0.1632(5)0.69550(19)0.0179(5)
H1AAa0.652399−0.0889400.6344800.022*
H1ABa0.605753−0.1886960.6704030.022*
N1Aa0.64941(6)−0.0095(3)0.79245(16)0.0150(4)
C10.61594(5)0.0703(3)0.84542(12)0.0172(3)
C3Ab0.72386(8)−0.2202(5)0.85912(19)0.0268(5)
H3AAb0.758564−0.2000310.8842080.032*
H3ABb0.711654−0.2960280.9196010.032*
C4Ab0.70071(7)0.0202(4)0.83457(18)0.0221(4)
H4AAb0.7063210.1164350.9027480.027*
H4ABb0.7148820.1031370.7789690.027*
C7b0.88425(5)−0.0648(3)1.23605(13)0.0200(3)
N1Bb0.6461(3)−0.1046(17)0.8302(6)0.0229(17)
C3Bb0.6741(3)−0.1908(19)0.6646(7)0.033(2)
H3Ab0.668880−0.2835070.5954100.039*
H3Bb0.670723−0.0216930.6451340.039*
O1Bb0.7211(2)−0.2362(17)0.7295(6)0.0385(19)
C4Bb0.7287(3)−0.083(2)0.8248(7)0.035(2)
H12Ab0.761660−0.1004810.8672080.042*
H12Bb0.7240180.0830560.8004560.042*
C5Bb0.6959(3)−0.1413(18)0.8945(7)0.032(2)
H13Ab0.701842−0.0397840.9609840.038*
H13Bb0.700271−0.3074530.9187040.038*
C2Bb0.6398(3)−0.2571(19)0.7294(8)0.023(2)
H15Ab0.644200−0.4245230.7515030.027*
H15Bb0.607240−0.2379080.6846520.027*
O2Ac0.7808(2)0.3381(8)1.0415(4)0.0241(8)
N2Ac0.85009(7)0.0104(4)1.15107(17)0.0150(4)
C5Ac0.79895(8)−0.0287(5)1.1431(2)0.0213(5)
H5AAc0.793880−0.1127001.2097900.026*
H5ABc0.786137−0.1276701.0778730.026*
C8Ac0.85855(8)0.1566(5)1.0594(2)0.0183(5)
H8AAc0.8489210.0694460.9889920.022*
H8ABc0.8928000.1931851.0701670.022*
C7Ac0.83047(8)0.3831(5)1.0539(2)0.0223(5)
H7ACc0.8418400.4748851.1223100.027*
H7ADc0.8358260.4786900.9907670.027*
C6Ac0.77320(12)0.2054(7)1.1329(3)0.0238(7)
H6ACc0.7387650.1768931.1249810.029*
H6ADc0.7842210.2975181.2013690.029*
N2Bd0.85459(12)0.1221(7)1.1920(3)0.0129(7)
C6Bd0.86342(15)0.2834(9)1.1047(4)0.0178(9)
H2Cd0.8955020.2554111.0903990.021*
H2Dd0.8616390.4488961.1286460.021*
C7Bd0.82628(16)0.2389(9)1.0006(4)0.0217(9)
H9AAd0.8318250.3467240.9417860.026*
H9ABd0.8294970.0754080.9753940.026*
C9Bd0.80589(14)0.1546(8)1.2098(3)0.0172(8)
H6AAd0.8022220.3160161.2370830.021*
H6ABd0.7997140.0414401.2659590.021*
C8Bd0.7710(2)0.1153(12)1.1023(5)0.0211(12)
H7AAd0.773330−0.0496841.0781470.025*
H7ABd0.7383660.1411041.1135470.025*
O2Bd0.7800(4)0.2726(15)1.0174(8)0.0224(15)
H1A0.4492(7)−0.179(4)0.8673(17)0.026(5)*
H3C0.9494(7)0.679(4)1.0831(17)0.026(5)*
H2A0.5467(7)0.691(4)0.9045(17)0.028(5)*
H4A1.0458(7)−0.198(4)1.1437(18)0.033(6)*
H2B0.5699(8)0.514(4)0.9506(16)0.030(6)*
H4B1.0680(8)−0.015(4)1.1179(17)0.034(6)*
H3D0.9294(8)0.608(4)0.9877(18)0.032(6)*
H1B0.4288(8)−0.110(4)0.9439(18)0.039(6)*

  1. Occupancies: a = 0.8, b = 0.2, c = 0.65, d = 0.35.

Experimental details

Crystal evaluation and data collection were done on a Bruker Smart APEX2 diffractometer [1]. The structure was solved by the direct method using the SHELXS [2] program and refined using SHELXL [2]. The visual crystal structure information was obtained using ORTEP-3 [3] system software. All hydrogen atoms were placed in idealized positions and refined in riding models with Uiso assigning values of 1.2 times those of their parent atoms and the distances of C—Hs were constrained to 0.99 Å for all the methylene H atoms and 0.84 Å for water hydrogens.

Both morpholine moieties are disordered over two positions (Table 2).

Discussion

Dithiocarbamate ligands are known to be flexible ligands that are able to form diverse types of complexes and be able to stabilize transition metal in various oxidation states [4], [5]. They may possess electrochemical and optical properties because of their redox behaviour and strong coordination ability [6]. They are known to be planar and sterically non-demanding ligands that can be automatically changed by having choices of substituents [7]. Their functionalization of substituents on the nitrogen atom of the dithiocarbamate moeity, can result in various complex structures through secondary interactions hence desirable physical properties [8]. The ease of formation of metal complexes is due to the electron delocalization around the N(CSS)- moiety which is also transferred to the metal centre [9]. This ability is recognized to the approval of dithiocarbamates and thioureide tautomers [10]. In dithiocarbamates, the sulfur atoms act as soft donor atoms containing a lone pair of electron localized on nitrogen (sp3) resulting in pyramidal arrangement of substituents. In thioureide systems there are donor ligands which are planar with lone pair of electron localized in the backbone of carbon-nitrogen bond and onto the sulfur atoms [10]. Dithiocarbamate ligands have been widely used in coordination chemistry due to diverse applications, for example used in dyes, agricultural and pharmaceutical industries and to chelate with heavy metals [11], [12], [13].

Dithiocarbamate ligands are mostly synthesized from nucleophilic addition reaction of primary or secondary amines with carbon disulfide in the presence of a strong base i.e. sodium/ potassium hydroxide acting as a proton acceptor [14]. The formation of these compounds is often accompanied by release of heat, hence the syntheses are carried out at low temperatures [15]. The title compound was as such prepared by the reaction morpholine 4-dithiocarbamate with sodium hydroxide in ethanol.

The asymmetric unit of the title compound contains two fragments of two chains of coordination polymers (see the figure). The fragments contain a morpholine 4-dithiocarbamate moiety and two water molecules coordinated to a sodium centre. The coordination of the two water molecules to the Na center results in four member metallacycles connected in alternating orthogonal fashion in the b crystallographic direction. Two S atoms from two morpholine moieties also in the same chains occupy the other coordination sites such that adjacent chains have the O containing sides of the chair conformed morpholine facing each other. The interaction between the sodium cation and water molecules does not disturb the geometric conformation of the ligand [16]. The S—Na bond distances are 3.0291(7) Å, while the S—C ones are 1.7151(15) Å and 1.7390(15) Å indicating a tendency towards a double bond character of electron density in the S—C—S group [17]. The C—S—Na bond angle is 132.42(5)°, while the S—C—S bond angle is 120.40(8)° and is similar to what is observed for similar complexes.

Acknowledgements

We acknowledge the University of KwaZulu-Natal and National Research Foundation of South Africa for financial support for Ekemini Akpan and Sizwe J. Zamisa.

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Received: 2018-11-19
Accepted: 2019-02-14
Published Online: 2019-03-26
Published in Print: 2019-06-26

© 2019 Nolwazi Solomane 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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  44. Crystal structure of 6-hydroxy-4,8,11b-trimethyltetradecayhdro-8,11-epoxy-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid – methanol (1/1), C20H30O4
  45. The crystal structure of aqua-bis(3-acetyl-2-oxo-2H-chromen-4-olato-κ2O,O′)zinc(II) monohydrate, C22H18O10Zn
  46. Crystal structure of poly[bis(μ2-4-bromoisophthalate-κ2O:O′)-tris(μ2-1-(3-((1H-1,2,4-triazol-1-yl)methyl)benzyl)-1H-1,2,4-triazole-κ2N:N′)dicobalt(II)] monohydrate, C26H23CoN9O5Br
  47. A cyclic I102− anion in the layered crystal structure of theophyllinium pentaiodide, C7H9I5N4O2
  48. Crystal structure of catena-poly[diaqua-bis(μ2-4-((4-(pyridin-2-ylmethoxy)phenyl)diazenyl)benzoato-κ3O,O′:N)cadmium(III)], Cd(C19H14O3N3)2(H2O)
  49. Crystal structure of catena-poly[(μ2-4,4′-bipyridyl-κN,N′)-bis(O,O′-dimethyldithiophosphato-κS)-zinc(II)], {C14H20N2O4P2S4Zn}n
  50. Crystal structure of 3-amino-2-hydroxy-6-methoxybenzamide hydrate, C16H22N4O7
  51. Crystal structure of hemikis(cyclohexane-1,4-diammonium) (pyridine-2-carboxylate), [C6H16N2]0.5[C6H4NO2]
  52. Crystal structure of 2-chloro-4-(prop-2-yn-1-yloxy)-6-(thiophen-2-yl)-1,3,5-triazine, C10H6ClN3OS
  53. The crystal structure of 3-butyl-1-methyl-1H-imidazol-3-ium catena-poly[tris(μ2-bromido-κ2Br:Br)lead(II)], C8H15Br3N2Pb
  54. Crystal structure of 3-(5-amino-1H-1,2,4-triazol-3-yl)-1-(piperidin-1-yl)propan-1-one, C10H17N5O
  55. Crystal structure of aqua-2,2′,2′′-(((nitrilo-κN-tris(ethane-2,1-diyl))tris(azanylylidene-κ3N′,N′′,N′′′))tris(methanylylidene))tris(4-chlorophenolato-κ3O,O′,O′′)neodymium(III), C27H26Cl3N4NdO4
  56. Crystal structure of dichlorido-(μ2-2,2′-(diazene-1,2-diyl)bis(benzen-1-ido)-κ2C:C′)dimercury(II), C12H8Cl2Hg2N2
  57. Crystal structure of (3E,5E)-3,5-bis(4-cyanobenzylidene)-1-((4-fluorophenyl)sulfonyl)piperidin-4-one, C27H18FN3O3S
  58. Crystal structure of dichlorido(pyridine-κN)(2,4,6-tri-2-pyridyl-1,3,5-triazine-κ3N2,N1,N6)nickel(II), C23H17Cl2N7Ni
  59. Redetermination of the crystal structure of tetrakis(4-chlorobenzyl)tin(IV), C28H24Cl4Sn
  60. The crystal structure of 2,6-bis(pyridin-1-ium-3-ylmethyl)hexahydro-4,8-ethenopyrrolo-[3,4-f] isoindole-1,3,5,7-tetrone tetrachloridocuprate(II) monohydrate, C24H24Cl4CuN4O5
  61. Crystal structure of cyclo-[octaaqua-tetrakis(μ2-5,5′-(1H-imidazole-4,5-diyl)bis(tetrazol-2-ido)-κ4N,N′,N′′,N′′′)tetramagnesium(II)], C20H24N40O8Mg4
  62. The crystal structure of a matrine derivative, 13-(4-Cl-pyrrole)-matrine, C18H26ClN4O
  63. Crystal structure of (dibenzyl sulphoxide-κO)bis(2-chlorobenzyl-κC1)dichloridotin(IV), C28H26Cl4OSSn
  64. Crystal structure of catena-poly[(μ2-azido-κ2N:N)(μ2-4-cyanobenzoato-κ2O:O′)-(μ2-methanol-κ2O:O)copper(II)], C9H8CuN4O3
  65. Crystal structure of 1,1′-dibenzyl-3,3′-dicyano-1,1′,4,4′-tetrahydro-4,4′-bipyridine, C26H22N4
  66. Crystal structure of (2-bromobenzyl)((1-bromonaphthalen-2-yl)methyl)sulfane, C18H14Br2S
  67. Crystal structure of 2-(4-ammoniocyclohexyl)-3-(pyridin-2-yl)imidazo[1,5-a]pyridin-2-ium 2-[(2-carboxylatophenyl)disulfanyl]benzoate dihydrate, [C18H22N4][C14H8O4S2] ⋅ 2H2O
  68. Crystal structure of (E)-N-((3R,5S,10S, 13S,14S,17S)-17-((S)-1-(dimethylamino)ethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)-2-methylbut-2-enamide – water – methanol (1/1/1), C29H54N2O3
  69. Crystal structure of methyl 2-(4-(3-(2,4-difluorophenyl)pyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C21H15F2N3O2
  70. Crystal structure of poly[triaqua-(μ4-benzene-1,3,5-tricarboxylato-κ5O1,O2:O3:O4:O5)-(μ2-5-(3-pyridyl)tetrazolato-κ2N1:N3)dizinc(II)], C15H13N5O9Zn2
  71. Crystal structure of N-(3-methylphenyl)(propan-2-yloxy)carbothioamide, C11H15NOS
  72. Crystal structure of poly[(μ2-1,3-bis(imidazol-1-ylmethyl)benzene-κ2N:N′)(nitrato-κ1O)cadmium(II)] — water (2/1), C28H32CdN10O7
  73. Crystal structure of 4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, C8H7N3S
  74. Crystal structure of benzyltrichloridobis(1H-pyrazole-κ2N)tin(IV), C13H15Cl3N4Sn
  75. Crystal structure of chlorido-4-fluorobenzyl-bis(2-methylquinolin-8-olato-κ2N,O)tin(IV), C27H22ClFN2O2Sn
  76. Crystal structure of tetrakis(O,O′-diisopropyldithiophosphato-κ2S,S′)-(μ2-1,2-bis(4-pyridylmethylene)hydrazine-κ2N:N′)zinc(II), C36H66N4O8P4S8Zn2
  77. Crystal structure of tetrabutylammonium 4,4-oxydibenzoate – boric acid – water (1/2/6) C46H98B2N2O17
  78. Redetermination of the crystal structure of catena-poly[[tribenzyltin(IV)]-(μ2-pyridine-4-carboxylato-κ2N:O)], C27H25NO2Sn
  79. The synthysis and crystal structure of cyclohexyl 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C18H15N3Cl2F6O3S
  80. The crystal structure of 5,7-bis(2-hydroxyethoxy)-2-phenyl-4H-chromen-4-one, C19H18O6
  81. Synthesis and crystal structure of (±)-Ethyl 5′-(difluoromethyl)-2-oxo-4′,5′-dihydrospiro[indoline-3,3′-pyrazole]-4′-carboxylate, C14H13F2N3O3
https://doi.org/10.1515/ncrs-2018-0512
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Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of (E)-2-(1-((2-aminophenyl)imino)ethyl)-5-fluorophenol, C14H13FN2O
  3. Crystal structure of (E)-2-(1-((2-aminophenyl)imino)ethyl)-4,6-dichlorophenol, C14H12Cl2N2O
  4. The crystal structure of (E)-1-(4-methoxyphenyl)-3-(2-nitrophenyl)triaz-1-ene C8H8N2O4
  5. Crystal structure of (E)-2-(((6-bromopyridin-2-yl)methylene)amino)-3′,6′-bis(ethylamino)-2′,7′-dimethylspiro[isoindoline-1,9′-xanthen]-3-one—methanol (1:1), C32H30N5O2Br ⋅ CH4O
  6. Crystal structure of 2,4-pentanedione bis(2,4-dinitrophenylhydrazone), C17H16N8O8
  7. Crystal structure of sodium morpholine-4-carbodithioate, (C5H12NNaO3S2)
  8. Crystal structure of 1,1′-(hexane-1,6-diyl)bis(3-ethyl-1H-imidazol-3-ium) bis(hexafluorido phosphate), C16H28F12N4P2
  9. Crystal structure of 5-(4-chlorophenyl)-3-(4-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole, C21H16ClFN2
  10. Crystal structure of catena-poly[diaqua-bis(3-carboxy-5-methoxybenzoato-κO)-(1,2-bis(imidazol-1-yl)ethane-κ2N:N′)cobalt(II)], C26H28CoN4O12, [Co(C9H6O5)2(H2O)2(C8H10N4)]
  11. The crystal structure of 3-cyclohexyl-1,5-dioxaspiro[5.5]undecane-2,4-dione, C15H22O4
  12. Crystal structure of (2,4-dimethoxybenzyl)triphenylphosphonium trifluoroacetate — trifluoroacetic acid (1/1), C31H27F6O6P
  13. Crystal structure of 4-tert-butyl-1-(2,6-dimethylphenyl)-1H-1,2,3-triazole, C14H19N3
  14. Crystal structure of 1,1′-methylenebis(4-tert-butylpyridinium) tetrachloridocobaltate(II) – dichloromethane (1:1), C20H30Cl6CoN2
  15. Crystal structure of (4,4′-(ethane-1,2-diylbis((nitrilo)(2-furylmethylylidene)))bis(3-methyl-1-phenyl-1H-pyrazol-5-olato-κ4N,N′,O,O′))-nickel(II)), C32H26N6NiO4
  16. Synthesis and crystal structure of bis{((E)-((4-((E)-1-(benzyloxyimino)ethyl)phenyl)imino)methyl)-2-phenolato-κ2N,O}copper(II), C44H38CuN4O4
  17. Crystal structure of catena-poly[diaqua-bis(3,5-dichloropyridine-4-carboxylato-κ1O)-bis(μ2-4,4′-bipyridine-κ2N:N′)cobalt(II)], C22H16Cl4CoN4O6
  18. The crystal structure of 2-(4-chloro-2,6-dinitrophenyl)-1-(4-chloro-3,5-dinitrophenyl)diazene 1-oxide, C12H4Cl2N6O9
  19. The crystal structure of 3-(1H-benzo[d]imidazol-2-yl)-7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydroquinolin — dimethylsulfoxide (1/1), C21H19ClFN3O2S
  20. The crystal structure of dichlorido-bis(1-butyl-1H-imidazole-κN)zinc(II), C14H24Cl2ZnN4
  21. (Z)-N-tert-butyl-1-(2-(3,5-dichlorobenzamido)phenyl) methanimine oxide, C18H18Cl2N2O2
  22. Crystal structure of diaqua-bis(3-carboxy-5-bromoisophthalato-κO)-bis(1-(3-(1H-benzo[d]imidazol-1-yl)propyl)-1H-benzo[d]imidazol-3-ium-κN)nickel(II) bis(3-carboxy-5-bromoisophthalate), C66H54Br4N8NiO18
  23. Crystal structure of poly[aqua(μ2-5-methoxyisophthalato-κ2O,O′:O′′)-(1,2-bis(imidazol-1′-yl)ethane-κ2N:N′)cobalt(II), C34H36Co2N8O12
  24. Crystal structure of poly[diaqua-bis(μ2-1-(4-(1H-imidazol-1-yl)benzyl)-1H-1,2,4-triazole-κ2N:N′)manganese(II)] terephthalate tetrahydrate, MnC32H38N10O10
  25. Crystal structure of the fluorescent fipronil derivative 5,5′-(methylenebis(azanediyl))bis(1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carbonitrile), C25H6N8O2Cl4F12S2
  26. Crystal structure of the phosphorescent complex diethyldithiophosphonato-κ2S,S′-bis(2-phenylpyridinato-κ2C,N)iridium(III), C26H26N2O2PS2Ir
  27. The crystal structure of 4,10-diethoxy-6H,12H-6,12-epoxydibenzo[b,f][1,5]dioxocine, C18H18O5
  28. Crystal structure of dichlorido-bis(N-benzyl-2-(quinolin-8-yloxy)acetamide-κ2N,O)copper(II) — ethyl acetate (1/1), C38H36N4O6Cl2Cu
  29. Synthesis and crystal structure of bis{4-methyl-2-((E)-((4-((E)-1-(benzyloxyimino)ethyl)phenyl)imino)methyl)phenolato-κ3N,O,O}copper(II), C92H84Cu2N8O8
  30. The crystal structure of 1,3,5-trinitro-4,6-diazidobenzene, C6HN9O6
  31. Crystal structure 1-cinnamyl-2-((Z)-styryl)-1H-benzo[d]imidazole — methanol (1/1), C24H20N2 ⋅ CH4O
  32. The crystal structure of poly[m2-aqua-tetraaqua-bis(m9-4-formylbenzene-1,3-disulfonato)tetrasodium(I) hydrate, C14H18O19S4Na4
  33. Crystal structure of 2-((2,8-bis(trifluoromethyl)quinolin-4-yl)(hydroxy)methyl)piperidin-1-ium trifluoroacetate, [C17H17F6N2O][C2F3O2]
  34. The crystal structure of bis(ferrocenecarboxylato-κ2O,O′)bis[4-(dimethylamino)pyridine-κN]copper(II) — acetonitrile(1/2), C40H44CuO4Fe2N6
  35. Crystal structure of poly[di-μ2-aqua)-diaqua-bis(μ6-4,4′,4′′-(benzene-1,3,5-triyltris(oxy))tribenzoato-κ6O1:O2:O3:O3:O5:O6)tricadmium(II)] dihydrate, C54H42Cd3O24
  36. The crystal structure of dichlorido(1,3-bis(2,6-diisopropyl-phenyl)-1H-3λ4-imidazol-2-yl)(3-phenyl-pyridine-κN)palladium(IV), C38H45N3Cl2Pd
  37. The crystal structure of 2-chloro-4-(prop-2-yn-1-yloxy)-6-phenyl-1,3,5-triazine, C12H8ClN3O
  38. The crystal structure of 2,6-di-tert-butyl-4-(phenyl(phenylsulfonyl)methyl)phenol, C27H32O3S
  39. Crystal structure of bis{μ2-bis{(((((1-methoxyimino)ethyl)phenyl)imino)methyl)-2-phenolato-κ3N,O:O}copper(II)}, C68H68Cu2N8O8
  40. Crystal structure of catena-poly[tetraaqua-bis(μ2-2-(4-carboxylatophenoxy)benzoato-κ2O:O′)-pentakis(pyridine-κ1N)dinickel(II)], C53H47N5Ni2O13
  41. Synthesis and crystal structure of 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-5-(3-methoxy-benzylamino)-4-trifluoromethanesulfinyl-1H-pyrazole-3-carbonitrile, C20H12N4Cl2F6O2S
  42. Redetermination of the crystal structure of bis(μ2-di-ethyldithiocarbamato-κ3S,S′:S;κ3S:S: S′)-hexacarbonyl-di-rhenium(I), C16H20N2O6Re2S4
  43. The crystal structure of (E)-N′-((2-hydroxynaphthalen-1-yl)methylene)-2-phenylacetohydrazide, C19H16O2N2
  44. Crystal structure of 6-hydroxy-4,8,11b-trimethyltetradecayhdro-8,11-epoxy-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid – methanol (1/1), C20H30O4
  45. The crystal structure of aqua-bis(3-acetyl-2-oxo-2H-chromen-4-olato-κ2O,O′)zinc(II) monohydrate, C22H18O10Zn
  46. Crystal structure of poly[bis(μ2-4-bromoisophthalate-κ2O:O′)-tris(μ2-1-(3-((1H-1,2,4-triazol-1-yl)methyl)benzyl)-1H-1,2,4-triazole-κ2N:N′)dicobalt(II)] monohydrate, C26H23CoN9O5Br
  47. A cyclic I102− anion in the layered crystal structure of theophyllinium pentaiodide, C7H9I5N4O2
  48. Crystal structure of catena-poly[diaqua-bis(μ2-4-((4-(pyridin-2-ylmethoxy)phenyl)diazenyl)benzoato-κ3O,O′:N)cadmium(III)], Cd(C19H14O3N3)2(H2O)
  49. Crystal structure of catena-poly[(μ2-4,4′-bipyridyl-κN,N′)-bis(O,O′-dimethyldithiophosphato-κS)-zinc(II)], {C14H20N2O4P2S4Zn}n
  50. Crystal structure of 3-amino-2-hydroxy-6-methoxybenzamide hydrate, C16H22N4O7
  51. Crystal structure of hemikis(cyclohexane-1,4-diammonium) (pyridine-2-carboxylate), [C6H16N2]0.5[C6H4NO2]
  52. Crystal structure of 2-chloro-4-(prop-2-yn-1-yloxy)-6-(thiophen-2-yl)-1,3,5-triazine, C10H6ClN3OS
  53. The crystal structure of 3-butyl-1-methyl-1H-imidazol-3-ium catena-poly[tris(μ2-bromido-κ2Br:Br)lead(II)], C8H15Br3N2Pb
  54. Crystal structure of 3-(5-amino-1H-1,2,4-triazol-3-yl)-1-(piperidin-1-yl)propan-1-one, C10H17N5O
  55. Crystal structure of aqua-2,2′,2′′-(((nitrilo-κN-tris(ethane-2,1-diyl))tris(azanylylidene-κ3N′,N′′,N′′′))tris(methanylylidene))tris(4-chlorophenolato-κ3O,O′,O′′)neodymium(III), C27H26Cl3N4NdO4
  56. Crystal structure of dichlorido-(μ2-2,2′-(diazene-1,2-diyl)bis(benzen-1-ido)-κ2C:C′)dimercury(II), C12H8Cl2Hg2N2
  57. Crystal structure of (3E,5E)-3,5-bis(4-cyanobenzylidene)-1-((4-fluorophenyl)sulfonyl)piperidin-4-one, C27H18FN3O3S
  58. Crystal structure of dichlorido(pyridine-κN)(2,4,6-tri-2-pyridyl-1,3,5-triazine-κ3N2,N1,N6)nickel(II), C23H17Cl2N7Ni
  59. Redetermination of the crystal structure of tetrakis(4-chlorobenzyl)tin(IV), C28H24Cl4Sn
  60. The crystal structure of 2,6-bis(pyridin-1-ium-3-ylmethyl)hexahydro-4,8-ethenopyrrolo-[3,4-f] isoindole-1,3,5,7-tetrone tetrachloridocuprate(II) monohydrate, C24H24Cl4CuN4O5
  61. Crystal structure of cyclo-[octaaqua-tetrakis(μ2-5,5′-(1H-imidazole-4,5-diyl)bis(tetrazol-2-ido)-κ4N,N′,N′′,N′′′)tetramagnesium(II)], C20H24N40O8Mg4
  62. The crystal structure of a matrine derivative, 13-(4-Cl-pyrrole)-matrine, C18H26ClN4O
  63. Crystal structure of (dibenzyl sulphoxide-κO)bis(2-chlorobenzyl-κC1)dichloridotin(IV), C28H26Cl4OSSn
  64. Crystal structure of catena-poly[(μ2-azido-κ2N:N)(μ2-4-cyanobenzoato-κ2O:O′)-(μ2-methanol-κ2O:O)copper(II)], C9H8CuN4O3
  65. Crystal structure of 1,1′-dibenzyl-3,3′-dicyano-1,1′,4,4′-tetrahydro-4,4′-bipyridine, C26H22N4
  66. Crystal structure of (2-bromobenzyl)((1-bromonaphthalen-2-yl)methyl)sulfane, C18H14Br2S
  67. Crystal structure of 2-(4-ammoniocyclohexyl)-3-(pyridin-2-yl)imidazo[1,5-a]pyridin-2-ium 2-[(2-carboxylatophenyl)disulfanyl]benzoate dihydrate, [C18H22N4][C14H8O4S2] ⋅ 2H2O
  68. Crystal structure of (E)-N-((3R,5S,10S, 13S,14S,17S)-17-((S)-1-(dimethylamino)ethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)-2-methylbut-2-enamide – water – methanol (1/1/1), C29H54N2O3
  69. Crystal structure of methyl 2-(4-(3-(2,4-difluorophenyl)pyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C21H15F2N3O2
  70. Crystal structure of poly[triaqua-(μ4-benzene-1,3,5-tricarboxylato-κ5O1,O2:O3:O4:O5)-(μ2-5-(3-pyridyl)tetrazolato-κ2N1:N3)dizinc(II)], C15H13N5O9Zn2
  71. Crystal structure of N-(3-methylphenyl)(propan-2-yloxy)carbothioamide, C11H15NOS
  72. Crystal structure of poly[(μ2-1,3-bis(imidazol-1-ylmethyl)benzene-κ2N:N′)(nitrato-κ1O)cadmium(II)] — water (2/1), C28H32CdN10O7
  73. Crystal structure of 4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, C8H7N3S
  74. Crystal structure of benzyltrichloridobis(1H-pyrazole-κ2N)tin(IV), C13H15Cl3N4Sn
  75. Crystal structure of chlorido-4-fluorobenzyl-bis(2-methylquinolin-8-olato-κ2N,O)tin(IV), C27H22ClFN2O2Sn
  76. Crystal structure of tetrakis(O,O′-diisopropyldithiophosphato-κ2S,S′)-(μ2-1,2-bis(4-pyridylmethylene)hydrazine-κ2N:N′)zinc(II), C36H66N4O8P4S8Zn2
  77. Crystal structure of tetrabutylammonium 4,4-oxydibenzoate – boric acid – water (1/2/6) C46H98B2N2O17
  78. Redetermination of the crystal structure of catena-poly[[tribenzyltin(IV)]-(μ2-pyridine-4-carboxylato-κ2N:O)], C27H25NO2Sn
  79. The synthysis and crystal structure of cyclohexyl 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C18H15N3Cl2F6O3S
  80. The crystal structure of 5,7-bis(2-hydroxyethoxy)-2-phenyl-4H-chromen-4-one, C19H18O6
  81. Synthesis and crystal structure of (±)-Ethyl 5′-(difluoromethyl)-2-oxo-4′,5′-dihydrospiro[indoline-3,3′-pyrazole]-4′-carboxylate, C14H13F2N3O3
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