Crystal and Molecular Structures of Two Triazole Derivatives: 4-Cyclopropyl-4,5-dihydro-1H-1,2,3-triazole and Methyl 1-benzyl-1H-1,2,3-triazole-4-carboxylate

Abstract  

The molecule in 4-cyclopropyl-4,5-dihydro-1H-1,2,3-triazole (I) is disposed about a mirror plane with the triazole ring lying in the plane and being orthogonal to the cyclopropyl ring. Considerable delocalization of π-electron density within the triazole ring is indicated by the pattern of bond distances in (I). The molecule of methyl 1-benzyl-1H-1,2,3-triazole-4-carboxylate (II) adopts a curved shape with the dihedral angle formed between the triazole and benzene rings being 63.23(8)°. By contrast to (I), localization of π-electron density within the triazole ring in (II) is indicated. Both (I), via N–H···N hydrogen bonding, and (II), via C–H···O and C–H···N interactions, associate in the solid state to form supramolecular chains. In (I), the chain is a zigzag with a flat topology, whereas in (II) the linear chain has a curved topology. Compound (I) crystallizes in the orthorhombic space group Pnma with a = 5.6470(2) ?, b = 7.3359(4) ?, c = 13.4404(7) ?, and Z = 4. Compound (II) crystallizes in the monoclinic space group P2₁/c with a = 12.1314(5) ?, b = 5.5951(2) ?, c = 16.4339(7) ?, β = 111.269(2)°, and Z = 4.     

Crystal structures of molecular complexes of 18-crown-6 with 2-aminobenzoic and 5-amino-1-benzyl-1,2,3-triazole-4-carboxylic acid hydrazides

The crystal structures of two host-guest molecular complexes of 18-crown-6 with 2-aminobenzoic acid hydrazide monohydrate (the ratio host: guest: H₂O = 1: 2: 2) (complex I) and 5-amino-1-benzyl-1,2,3-triazole-4-carboxylic acid hydrazide (the host: guest ratio = 1: 2) (complex II) are determined by X-ray diffraction analysis. Crystals I are monoclinic, a = 8.468(2) Å, b = 17.378(3) Å, c = 10.517(2) Å, β = 96.88(3)°, space group P2₁/n, and R = 0.0393 for 6692 reflections. Crystals II are orthorhombic, a = 18.489(1) Å, b = 10.192(3) Å, c = 20.412(2) Å, space group Pbca, and R = 0.0540 for 3513 reflections. In both complexes, the centrosymmetric 18-crown-6 and guest molecules are joined together through the NH?O (crown) hydrogen bonds, which involve all the hydrogen atoms of the hydrazine group. The NH?O=C intramolecular hydrogen bond is observed in the guest molecule. In structure I, the water molecule serves as a bridge between the guest molecules related by the glide-reflection plane and combines the guest-host-guest complexes into layers. In structure II, the guest molecules are linked into chains through hydrogen bonds of the NH?O=C type; in turn, the chains composed of guest molecules and the crown ether molecules bonded to these chains form a layered structure.     

Crystal and molecular structure of 4-bromo-2,2,3,3-tetramethyl-1-benzyl-1-phenylphosphetanium bromide

The title compound crystallizes in the monoclinic space groupP2₁/n, witha=8.881(1),b=17.718(1),c=13.077(8) Å,=99.17(2)° andZ=4. The structure was solved by the heavy-atom method and refined to a finalR value of 0.059. The four-membered ring is nonplanar, with a puckering angle of 22.0°. The Br and phenyl are in pseudoaxial positions and aretrans to each other in the solid state.     

Crystal structure of 4,6-dinitro-1-(5-tetrazolyl)-1H-indazole trihydrate

The title compound, C₈H₄N₈O₄·3H₂O, crystallizes in space groupP¯1 with cell constantsa=7.022(1),b=9.507(2),c=10.906(2) Å,=84.99(1),=71.89(1),=72.56(1)°,Z=2, andV _c =660.2 ų. The structure was solved by direct methods using diffractometer data and was refined by full-matrix least-squares methods to anR value of 0.060 for 2112 observed reflections. The molecule, consisting of a phenyl ring fused to a pyrazole ring with a tetrazole ring connected to it equatorially, is planar except for the N(7) nitro-group oxygen atoms. The structure is stabilized by a three-dimensional network of O-HO, O-HN, and N-HO hydrogen bonds through the water molecules.     

Crystal and molecular structure of 4-amino-4-carboxyl thiapyran

4-Amino-4-carboxylthiapyran crystallizes in space groupP2₁/c witha = 10.61,b = 6.55,c= 10.97 Å, =96.3 °, andZ = 4. The structure was solved by the heavy-atom method, with 897 observed reflections, and refined to anR of 0.093. The packing of the structure is found to be very similar to that in the structure of 1-aminocyclohexane carboxylic acid. The conformation of the thiapyran ring exists in the puckered chair form.Contribution No. 410 from the Dept. of Crystallography and Biophysics, Univeristy of Madras, Guindy Campus, Madras-600025, India.     

Crystal and molecular structure of 5-amino-1,2,3,4-thiatriazole

The crystal structure of 5-amino-1,2,3,4-thiatriazole has been determined from three-dimensional counter data and refined by full-matrix least-squares techniques. The crystals belong to the monoclinic space groupP2₁/n witha = 3.780(2),b = 10.179(5),c = 10.139(5) Å, = 91.78(4) °, andD _x = 1.74 g cm^–3 forZ = 4. The finalR factor for 572 observed reflections is 0.042. This structure represents the first X-ray structure determination of an ammosubstituted thiatriazole, although electron diffraction and CNDO calculations have been carried out on related systems. The results show that the discrepancy between the observed reactivity and that calculated might be due to the fact that 5-substitution appreciably affects the -system of the heteroaromatic ring.     

Crystal structure of potassium sodium tartrate trihydrate

Crystals of potassium sodium tartrate trihydrate (dl-KNaC₄H₄O₆ · 3H₂O) were obtained from an aqueous solution. The crystal shape was described. The atomic structure of the compound was determined and compared with the known structures of dl-KNaC₄H₄O₆ · 4H₂O and l-KNaC₄H₄O₆ · 4H₂O.     

Crystal and molecular structure of 4-amino-4-carboxyl thiapyran hydrobromide

Journal of Chemical Crystallography - 4-Amino-4-carboxylthiapyran hydrobromide crystallizes in the monoclinic space groupP21/m, witha= 9.72 Å,b= 6.60 Å andc=7.10 Å,β = 94.8...     

Crystal and molecular structure of (2-amino-4-methyl-1-pyridinio) cyanoborane

The crystal structure of the title compound, C₇H₁₀N₃B, has been determined by X-ray diffraction using CuK radiation. The crystals are monoclinic,P2₁/c witha=6.941(2),b=15.961(3),c=7.739(2) Å,=90.5(2)° andZ=4. The structure was solved by direct methods, and refined by full matrix least squares to a finalR-value of 056 with 833 observed reflections. The molecule is in the elongated form, but is not planar; the torsion angle C(2)-N(1)-B-C(8) is 82.9(4)°. The bond distances N(1)-B=1.587(5) Å; B-C(8)=1.586(6) Å; C(8)N(3)=1.134(5) Å. The B-C-N moiety is slightly [176.9(4)°] nonlinear. The molecules are linked by weak hydrogen bonds N(2)-H(1N)N(3), N(2)-N(3)=3.055(5) Å and N(2)-H(2N)N(3), N(2)-N(3)=3.165 Å.     

Crystal and molecular structure of 1-amino-1-methylethylphosphonic acid monohydrate

The crystal and molecular structure of 1-amino-1-methylethylphosphonic acid monohydrate (C₃H₁₀NO₃P·H₂O) has been determined by single-crystal X-ray diffraction methods. The crystals are orthorhombic:Pna2₁,a=11.665(2),b=9.415(1),c=6.386(1) Å,Z=4. The structure was solved by the heavy-atom method and refined to a finalR=0.028. The molecule exists as a zwitterion, H ₃ ⁺ N-C-(CH₃)₂-PO₃₄H^–. There are six independent hydrogen bonds in the structure, three of the type N-HO with lengths 2.904(5), 2.745(6), and 2.765(5) Å and three of the type O-HO with lengths 2.754(4), 2.833 (7), and 2.548(5) Å.     

Synthesis,Characterization and Crystal Structure of Ethyl 2-amino-4-(4-fluorophenyl)-6-phenylcyclohexa-1,3-diene-1-carboxylate

Ethyl 2-amino-4-(4-fluorophenyl)-6-phenylcyclohexa-1,3-diene-1-carboxylate was synthesized from ethyl 6-(4-bromophenyl)-4-(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate and ammonium acetate in glacial acetic acid. The synthesized compound was characterized by elemental analysis, FT-IR, thermogravimetric analysis (TGA), differential thermal analysis (DTA), UV-Visible, and single-crystal X-ray diffraction. The title compound, ethyl 2-amino-4-(4-fluorophenyl)-6-phenylcyclohexa-1,3-diene-1-carboxylate, C₂₁H₂OFNO₂, crystallizes in the orthorhombic space group Pbca with the following unit-cell parameters: a = 17.417(2), b = 9.7287(9), c = 21.014(2) Å, and Z = 8. The crystal structure was solved by direct methods using single-crystal X-ray diffraction data collected at room temperature and refined by full-matrix least-squares procedures to a final R-value of 0.0644 for 1616 observed reflections. An intramolecular N–H…O hydrogen bond generates an S(6) graph-set motif. In the crystal, molecules are linked by N–H…O hydrogen bonds, forming a two-dimensional network.     

Molecular complexes of 3-amino-1,2,4-triazole: The crystal structure of 3-amino-1,2,4-triazolium 5-nitrofuran-d2-carboxylate

3-Amino-1,2,4-triazolium (3-AT) 5-nitrofuran-2-carboxylate has been prepared and its x-ray crystal structure reported (a = 12.363(3) Å, b = 12.5720(10) Å, c = 12.8550(10) Å, Pbca, orthorhombic, Z = 8, and D _c = 1.604 mg m^–3). The solid-state packing of this organic acid-base salt consists of a three-dimensional hydrogen-bonded network which exhibits a cage-like repeat unit involving both the N(2)–H and N(4)–H sites of 3-AT. A review of five such structures reveals that in all cases the carboxylate groups interact with either of these sites [and the N(31)H₂] and form a R ² ₂(8) graph set interaction. Analysis of all 3-AT complexes which form this interaction reveals that the hydrogen-bonding distances between the non-hydrogen atoms are not equal [av. 2.712(5) Å and 2.897(5) Å], with the shorter distance being the interaction between the heterocyclic nitrogen and the corresponding carboxylate oxygen. Furthermore, a review of the interactive modes of all 3-AT adducts has been undertaken.     

Crystal structure of 1β-methyl-4α-isopropylcyclohexyl-spiro-5′-hydantoin

The crystal structure of 1-methyl-4-isopropylcyclohexyl-spiro-5-hydantoin has been determined by single-crystal X-ray diffraction techniques, and refined by full-matrix least-squares methods. The molecule C₁₂H₂₀N₂O₂·H₂O crystallizes with one molecule of water in the orthorombicP2₁2₁2₁ space group, witha=15.869(5),b=14.043(4),c=6.240(2) Å, andZ=4; the finalR factor was 0.032. The X-ray results showed that both substituents (methyl and isopropyl) in the cyclohexyl ring are in thetrans configuration. The configuration of the molecule is in agreement with suggestions of organic chemists.     

The Crystal Structures of Some 1-Aryl-5-methyl-1,2,3-triazole Derivatives

Abstract  The two 1-aryl-5-methyl-1,2,3-triazole derivatives were prepared by the 1-aryl-5-methyl-1,2,3-triazol-4-carboxylic acids 3. The yielded products 4a–b were confirmed by NMR, MS, IR spectra. We investigated the crystalline structure of compounds 4a and 4b. Compound 4a, C₉H₈BrN₃, Mr = 238.09, crystallizes in the monoclinic space group P2(1)/n with unit cell parameters a = 11.660(2), b = 7.668(2), c = 11.818(2) ?, α = 90.00, β = 116.01(3), γ = 90.00o. V = 949.6(3) ?³, Z = 4, Dx = 1.665 Mg m⁻³. The final R was 0.0477. Compound 4b, C₁₃H₁₁N₃, Mr = 209.25, crystallized in the orthorhombic space group Pbca with unit cell parameters a = 10.373(2) ?, b = 11.691(2) ?, c = 17.579(4) ?, α = 90.00o, β = 90.00o, γ = 90.00o, V = 2131.8(7) ?³, Z = 8, D _m = 1.304 Mg m⁻³. The final R was 0.0565. Index Abstract  The two 1-aryl-5-methyl-1,2,3-triazole derivatives were prepared by the 1-aryl-5-methyl-1,2,3-triazol-4-carboxylic acids 3. The yielded products 4a–b were confirmed by NMR, MS, IR spectra. We investigated the crystalline structure of compounds 4a and 4b. Compound 4a, C9H8BrN3, Mr = 238.09, crystallizes in the monoclinic space group P2(1)/n with unit cell parameters a = 11.660(2), b = 7.668(2), c = 11.818(2)  ?, α = 90.00, β = 116.01(3), γ =90.00o. V = 949.6(3) ?³, Z = 4, Dx = 1.665 Mg m⁻³. The final R was 0.0477. Compound 4b, C13H11N3, Mr = 209.25, crystallized in the orthorhombic space group Pbca with unit cell parameters a = 10.373(2) ?, b = 11.691(2) ?, c = 17.579(4) ?, α = 90.00o, β = 90.00o, γ = 90.00o, V = 2131.8(7) ?³, Z = 8, D _m = 1.304 Mg m⁻³. The final R was 0.0565.      

The Synthesis and Crystal Structure of 5-Methyl-1-(1-naphthyl)-1,2,3-triazol-4-carboxyl Acid

Abstract  5-Methyl-1-(1-naphthyl)-1,2,3-triazol-4-carboxyl acid 3 was synthesized from 1-aminonaphthalene. The yielded product 3 was investigated with X-ray crystallographic, NMR, MS and IR techniques. Compound 3, C₁₄H₁₁N₃O₂, Mr = 253.26, crystallizes in the orthorhombic space group Pbca with unit cell parameters a = 10.068(2), b = 12.353(2), c = 20.102(4) ?, V = 2500.1(8) ?³, Z = 8, Dx = 1.346 Mgm^-3. The final R was 0.0474. The molecular packing is stabilized by intermolecular O–H···N interactions. Index Abstract  5-Methyl-1-(1-naphthyl)-1,2,3-triazol-4-carboxyl acid 3 was synthesized from 1-aminonaphthalene. The yielded product 3 was investigated with X-ray crystallographic, NMR, MS and IR techniques. Compound 3, C₁₄H₁₁N₃O₂, Mr = 253.26, crystallizes in the orthorhombic space group Pbca with unit cell parameters a = 10.068(2), b = 12.353(2), c = 20.102(4) ?, α = β = γ = 90.00o. V = 2,500.1(8) ?³, Z = 8, Dx = 1.346 Mgm⁻³. The final R was 0.0474. The molecular packing is stabilized by intermolecular O–H···N interactions.      

Crystal structure of dicalcium potassium trihydrogen bis(pyrophosphate) trihydrate

The crystal structure of Ca₂KH₃(P₂O₇)₂·3H₂O has been determined by single crystal X-ray diffraction. Crystals are monoclinic, space groupP2₁/n witha=10.518(3),b=19.253(9),c=7.340(3)Å,=90.07(2)°, andZ=4. The structure was refined toR=0.048 andR _w=0.044 for 1839 reflections withI3(I). The structure consists of a compact assembly of Ca, K, HP₂O₇, and H₂P₂O₇ ions and three water molecules arranged in layers perpendicular to theb-axis. The two independent Ca ions and the HP₂O₇ ion comprise one layer; K and H₂P₂O₇ ions and the three water molecules form an interstitial layer. Coordinations of the two independent Ca ions are quite similar, but the environments of HP₂O₇ and H₂P₂O₇ ions are quite different, probably due to their locations in different layers. The general structural features are quite similar to those of Ca(NH₄)HP₂O₇.Certain commercial materials and equipments are identified in this paper to specify the experimental procedure. In no instance does such identification imply recommendation or endorsement by the National Institute of Standards and Technology or the ADA Health Foundation or that the material or equipment identified is necessarily the best available for the purpose.     

Crystal structure of 2-amino-3-methylpyridinium ortho-phthalate

A new crystal of 2-amino-3-methylpyridinium ortho-phthalate has been prepared and characterized by X-ray crystallography. The salt crystallizes in the monoclinic space group P2₁/c with a = 11.015(2) Å, b = 11.057(2) Å, c = 15.767(2) Å, = 90.00°, = 96.220(10)°, = 90.00°, V = 1909.0(5) ų, Z = 4. In the cell unit, the phthalate anion is linked with two pyridinium cations by NHO hydrogen bond on both sites of annular and exocyclic nitrogen atoms. The two pyridinium cations are arranged in a face-to-face pattern with a dihedral angle of 7.3° and a shortest aspectant distance of 3.4(1) Å between them, indicating the existence of – interaction. The C(5) atom is an electron donating center. The exocyclic N atom is an electron receiving center, which is consistent with features of imino resonance evidenced by bond lengths and angles. In the cell unit, two entities of pyridinium cation are aligned with each other in a face-to-face manner of electron receiving to donating center.