The crystal structure of the molecular complex of camphoramic acid with mandelic acid: A partial separation of a racemic mixture of mandelic acid by (1R,3S)-camphoramic acid

From an ethanol/water solution containing (1R,3S)-camphoramic acid and a racemic mixture of mandelic acid, the title complex crystallizes in the space group P2₁2₁2₁ with a = 8.015(2), b = 11.041(2), c = 21.781(4) Å. Both molecular complexes, the (1R,3S)-camphoramic acid (S)-mandelic acid complex and the (1R,3S)-camphoramic acid (R)-mandelic acid complex, randomly distribute in a disordered crystal structure with an approximate molar ratio of 3:1, thus a 3:1 separation of the mandelic acid enantiomers was achieved. Molecules of (S)-mandelic and (R)-mandelic acid form very similar intermolecular interactions with adjacent camphoramic acid and water molecules in the structure. This results in the formation of a cocrystal containing two diastereomers. The crystal structure consists of camphoramic acid layers and mandelic acid layers. An extensive H-bonding network occurs within and between the layers.     

Synthesis and crystal structure of 2-benzoyl-4-methyl phenyl benzoate

The crystal structure of the title compound, C₂₁H₁₆O₃, has been determined. The compound crystallizes in triclinic space group PĪ with cell parameters a = 9.2240(9) Å, b = 9.8050(8) Å, c = 10.1610(11) Å, α = 94.749(6)^∘, β = 112.544(4)^∘, γ = 102.145(6)^∘ and Z = 2. The structure exhibits both intra and intermolecular interactions of the type C–H ⋅s O. The intermolecular interaction between the molecules form centrosymmetric dimers.     

Structure of tetrahydro-2-naphthyl-4H-1,3,6,2-dioxazaboracine

Intramolecular B-N coordination occurs in tetrahydro-2-naphthyl-4H-1,3,6,2-dioxazaboracine, 2: (R = 2-naphthyl; R = H) both in the solid state and in CDCl₃ solution. Compound 2: (R = 2-naphthyl; R = H) crystallizes in the orthorhombic space group P2₁2₁2₁ (Z = 4), with a = 9.266(6), b = 11.034(8), c = 12.0635(10) Å. Molecules are linked, in the solid state, into spiral chains. As only one of the two oxygen atoms present in each molecule is involved in H-bonding, the boron and nitrogen centres are chiral. The intramolecular B-N bond length is 1.671(4) Å; other geometric parameters are B-O bond lengths of 1.448(4) and 1.464(4) Å, a B-C bond length of 1.598(4) Å, and bond angles at B between 100.6(3) and 115.4(3)°. The ¹¹B value for 2 (R = 2-naphthyl, R = H) at 25°C in CDCl₃ solution is 10.7 ppm.     

Crystal structures of 2,4,9-trimethyl-(3ar,4c,9c,9ac)-3a,4,9,9a-tetrahydro-benzo[?] isoindole-1,3-dione(endo), C15H17NO2 (1), and 2-methyl-(3ac,9ac)-3a,4,9,9a-tetrahydro-4r,9c-ethano-benzo[?]isoindole-1, 3-dione(endo), C15H15NO2 (2)

The title compounds crystallize in the space group P-1 (compound 1), with a = 7.198(2) Å, b = 7.965(2) Å, c = 12.707(2) Å, α = 72.05(1)^∘, β = 87.65(2)^∘, γ = 65.18(2)^∘ and Pbca (compound 2), with a = 8.156(3) Å, b = 13.177(3) Å, c = 22.742(4) Å. The chiral centers in both compounds C3a, C4, C9, C9a are either R, S, R, S or S, R, S, R (compound 1) and either R, R, S, S or S, S, R, R (compound 2) because of the centric space group.     

Crystal structure of 4-methyl-2-phenylbenzo[de]cyclobut[i] isoquinoline-3,5(2H)-dione

4-Methyl-2-phenylbenzo[de]cyclobut[i]isoquinoline-3,5(2H)-dione, C₂₁H₁₅NO₂, resulted from the photochemical reaction of N-methyl-1,8-naphthalenedicarboximide with phenylacetylene, has been characterized by ¹H NMR, IR, and MS spectra and established by single-crystal X-ray crystallography. The crystal structure belongs to the monoclinic space group P2₁/n with cell parameters a = 12.530(2) Å, b = 9.324(2) Å, c = 13.296(2) Å, = 96.85(1), V = 1542.3(4) ų, and Z = 4.     

X-ray crystal structure of cytochalasin D produced by Tubercularia sp., a novel endophytic fungus of Taxus mairei

The crystal structure of cytochalasin D, which was isolated from Tubercularia sp., a novel endophytic fungus of Taxus mairei, and cocrystallized with dimethyl sulfoxide, is reported. The title compound crystallizes in the monoclinic space group P2₁, with a = 7.583(6) Å, b = 11.053(10) Å, c = 18.632(10) Å, = 95.79(6)°, V = 1553.6(3) ų, Z = 2. The structure was solved by direct methods and refined by least-squares methods to a final R factor of 0.103 for 2937 independent reflections.     

Reactivity of 1,2,4,5-tetracarboxylatebenzene with cobalt(II)

The complexes [Co(H₂O)₆][Co(BTCA)(H₂O)₄]⋅7.2H₂O (1) and [Na₂Co(H₂O)₄(μ-H₂O)₂ (μ-BTCA)] (2) (BTCA = 1,2,4,5-tetracarboxylatebenzene) have been synthesized and characterized by single crystal X-ray diffraction. Compound (1) crystallizes in the triclinic space group P-1 with a = 6.8591(9) Å, b = 9.9691(13) Å, c = 10.9231(11) Å, α = 93.021(2)^∘, β = 104.883(2)^∘, and γ = 103.702^∘ with Z = 1. This compound exhibits a 1-dimensional structure of two alternating layers. A chain of cobalt ions and BTCA constitute one layer. Cobalt complex ions and solvent water molecules occupy the other. Compound (2) crystallizes in the monoclinic space group C 2/m with a = 8.8647(6) Å, b = 10.5247(7) Å, c = 21.2265(14) Å, and β = 92.525(2)^∘, with Z = 2. This compound consists of a 3-dimensional network of cobalt and sodium ions linked by BTCA. The sodium complex moiety is disordered around a center of inversion.     

Crystal structures of a pair of diastereomeric 3-(N,N-dimethylammonium)-1,1-diphenyl-1-butanol O,O′-di-p-toloyl hydrogen tartrates

The crystal structures of a pair of diastereomeric salts of (–)-(2R, 3R)-O, O-di-p-toloyl tartaric acid and (–)- and ( + )-3-N,N-dimethylamino-1,1-diphenyl-1-butanol have been determined. Crystal data: 3: (-)-(R)-C₁₈HC₂₄NO⁺(-)-(2R,3R)-C₂₀H₁₇O^- ₈ orthorhombic, P2₁2₁2₁, a = 7.873(2), b = 15.343(3), c = 28.76(1) Å, V = 3474(2) ų, Z = 4, and D _calc = 1.254 g cm^–3. 4: (+)- (S)-C₁₈H₂₄NO⁺, (-)-(2R,3R)-C₂₀H₁₇O^- ₈orthorhombic, P2₁2₁2₁, a = 7.504(1), b = 17.215(2), c = 26.490(4) Å, V = 3422.0(8) ų,Z = 4, and D _calc = 1.273 g cm^–3. The geometries and the conformational energies of the solid state conformations of the cations have been compared with global and local energy minimum conformations determined by molecular mechanics calculations. In the solid state, one conformation with and one without an intramolecular hydrogen bond are observed. The calculated global energy minimum conformation in aqueous solution contains the intramolecular hydrogen bond.     

Crystal structures of the cis and trans isomers of a tetrathia[3.3.3.3]cyclophane

Both the cis and trans isomers of 3,11,18,26-tetrathiatricyclo[26.2.2.1^5,9.2^13,16.1^20,24] hexatriaconta-5,7,9,20,22,24-hexene have been prepared and structurally characterized. Each of these centrosymmetric tetrathia dimers includes two cyclohexane rings in chair conformations with either 1,4-cis or 1,4-trans bonding and two meta-substituted benzene rings. The cis isomer packs into the monoclinic space group P2₁/a with a = 10.485(3)Å, b = 10.3956(18)Å, c = 14.1343(10)Å, = 105.200(13)°, Z = 2 and refined to an R factor of 0.046. The trans isomer crystallizes in the monoclinic space group P2₁/c with a = 10.7217(12)Å, b = 5.6797(7)Å, c = 25.415(5)Å, = 96.001(12)°, Z = 2 and refined to an R factor of 0.043. In the cis structure each benzene ring faces a cyclohexane ring while in the trans structure the cyclohexane rings face one another.     

Keto–enol tautomerism, conformations, and structure of 1-[N-(4-chlorophenyl)]aminomethylidene-2(1H)naphthalenone

1-[N-(4-chlorophenyl)]aminomethylidene-2(1H)naphthalenone (C₁₇H₁₂NOCl) (1) was synthesized and the crystal structure was determined. Compound 1 crystallizes in the monoclinic space group P2₁/n with a = 4.761(3) Å, b = 20.347(1) Å, c = 13.773(2) Å, = 92.89(3)°, V = 1332.4(3) ų, Z = 4, D _c = 1.404 g cm^–3, (Mo K) = 0.28 mm^–1, and R = 0.036 for 2680 reflections [I > 2(I)]. Molecule 1 is not planar, and the dihedral angle between the naphthaldeyde plane A [C1–C11, 01] and the 4-chloroaniline plane B [C12–C17, C11, N1] is 20.1(3)°. An intramolecular hydrogen bond occurs between the hydroxyl oxygen and imine nitrogen atoms [2.528(3) Å]. IR, ¹H NMR, and UV measurements and AM1 semiempirical quantum mechanical calculations support the keto form found in the X-ray structure.     

4- and 5-nitro-2-benzoylbenzoic acid

The structures of two isomeric nitro 2-benzoylbenzoic acids have been determined. 4-Nitro-2-benzoylbenzoic acid, C₁₄H₉NO₅, monoclinic, P2₁/c, a = 9.455(5), b = 6.632(2), c = 21.333(7)Å, = 107.96(3)°, Z = 4, V = 1270.6(9)ų, 5-nitro-2-benzoylbenzoic acid, C₁₄H₉NO₅, monoclinic, P2₁/c, a = 10.201(6), b = 8.515(4), c = 14.573(7)Å, = 101.35(4)°, Z = 4, V = 1241.1(11)ų. Both carboxylic acids form the usual H-bonded dimers across crystallographic centers of inversion. The nitro groups are essentially in the ring planes, and the interplanar angle between the mean planes described by the atoms of the benzoyl substituents and those of the benzoic acid aryl rings are 69(1)° and 84(1)°, respectively. The lower cell volume, higher density, and lower solubility in ethyl ethanoate correlates with the greater packing efficiency in 5-nitro-2-benzoylbenzoic acid.     

Solid-state formation of an inclusion compound of cholic acid withp-toluidine

Cholic acid undergoes solid-solid reactions with some aromatic molecules to form inclusion compounds. Simple shaking of a mixture of powdered cholic acid andp-toluidine results in formation of the 11 (host:guest) inclusion compound which has the same structure as that formed by conventional crystallization methods: monoclinic space groupP2₁ witha=13.577(4),b=8.078(2),c=14.182(6) Å, =114.42(3)°,Z=2 andR ₁=0.061 for 2680 unique reflections.     

Hydrogen bonding in labdane diterpenoids, labda-7,12(E),14-triene-17-oic acid and labda-12(Z),14,17-triene-18-oic acid

Two labdane diterpenoids, labda-7,12(E),14-triene-17-oic acid (1) and labda-12(Z),14,17-triene-18-oic acid (2), C₂₀H₃₀O₂, have been isolated from Croton oblongifolius. Both 1 and 2 crystallized in the monoclinic system, space group C2, with cell dimensions of a = 21.912(1) Å, b = 7.4002(4) Å, c = 11.5079(7) Å, = 101.999(1)^o and a = 21.308(2) Å, b = 11.9067(9) Å, c = 7.5606(6) Å, = 100.763(1)^o, respectively. Compound 1, a rare example of carboxylic group bound to a cyclohexene ring, forms an infinite intermolecular hydrogen-bonded polymer [O1 O2(–x + 1/2, y + 1/2, –z + 2) 2.697(2) Å], whereas molecules of compound 2 are linked to form an asymmetric hydrogen-bonded dimer [O1 O2(–x, y, –z) 2.657(3) Å].     

Synthesis and crystal structure of a novel 3D supramolecular complex [Na(DC18C6-B)][Ni(mnt)<Subscript>2</Subscript>]

A supramolecular complex [Na(DC18C6-B)][Ni(mnt)₂] (1) (DC18C6-B = cis-anti-cis-dicyclohexyl-18-crown-6, isomer B; mnt = maleonitriledithiolate) has been prepared and characterized by elementary analysis, FT-IR spectroscopy and X-ray single crystal diffraction. It crystallizes in triclinic, space group P1 with crystallographic data: a = 7.974(4) Å, b = 14.343(7) Å, c = 15.559(8) Å, α = 96.230(8)^∘, β = 100.361(8)^∘, γ = 93.849(9)^∘, V = 1733.2(15) ų, Z = 2, D_calcd = 1.408 g/cm³, F(000) = 766, R₁ = 0.0491, wR₂ = 0.1018. The formula unit contains one [Na(DC18C6-B)]⁺ complex cation and one [Ni(mnt)₂]⁻ complex anion, which are constructed into an infinite chain-like structure through Na–N bonds. The resulting chains crisscross on the [Ni(mnt)₂]⁻ complex anions and further assemble into an unusual 3D supramolecular framework via the weak interactions.     

Terbium and holmium trans-2,3-dimethylacrylic acid complexes with 1,10-phenanthroline

Novel dinuclear complexes, [REL₃(phen)]₂ (where RE = Tb, Ho; HL = trans-2,3-dimethylacrylic acid; phen = 1,10-phenantheoline), were synthesized and determined by elemental analysis, infrared absorption spectra (IR), thermogravimetric analysis (TGA), and X-ray diffraction. The Tb complex crystallizes in space group P2_1/n with the cell dimensions a = 12.939(2) Å, b = 13.018(2) Å, c = 15.400(3) Å and = 94.72(1)°. The Ho complex crystallizes in P ⁽⁹⁾ with a = 12.406(3) Å, b = 13.280(3) Å, c = 9.823(2) Å, = 110.80(2)°, = 103.42(2)°, = 63.67(1)°. The Tb atom is nine coordinate and the separation of Tb...Tb* is 3.97 Å. The Ho atom is eight coordinate and the separation of Ho...Ho* is 4.01 Å.     

Ortho-metalation and carboxylate coordination in the reaction between the dipotassium salt of phthalic acid and Cp*Ir(PMe3)Cl2: X-ray diffraction structure of Cp*Ir(PMe3)[C6H3(CO2)(CO2H)]

The cyclopentadienyl complex Cp*Ir(PMe₃)Cl₂ reacts with the dipotassium salt of phthalic acid in the presence of AgPF₆ via chloride substitution to give the ortho-metalated compound Cp*Ir(PMe₃)[C₆H₃(CO₂)(CO₂H)]. This new compound has been isolated by recrystallization and has been characterized in solution by ¹H and ¹³C NMR spectroscopies, and the solid-state structure has been verified by X-ray crystallography. Cp*Ir(PMe₃)[C₆H₃(CO₂)(CO₂H)] crystallizes in the monoclinic space group P2₁/c, a = 9.1010(6) Å, b = 16.715(1) Å, c = 14.3965(9) Å, = 108.24(1)°, V = 2080.0(2) ų, Z = 4, and d _calc = 1.813 mg/m³; R = 0.0276, R _w = 0.0810 for 2730 reflections with I > 2(I). Coordination of the benzene ring to the iridium center via one of the carboxylate groups and ortho-metalation of the C–H moiety that was to the iridium-bound carboxylate group is confirmed.     

Preparation and crystal structure of tungstogallate acid H5GaW12O40

The heteropoly tungstogallate acid H₅GaW₁₂O₄₀ has been synthesized and characterized. Colorless octahedral crystals of the title compound were crystallized from acetonitrile with formula H₅GaW₁₂O₄₀. The single crystal X-ray structure analysis of the title compound revealed that it crystallized in monoclinic system, space group Cm with a = 17.691 (4) Å, b = 25.065 (5) Å, c = 15.315 (3) Å, = 125.21 (3)°, V= 5548.5 (19) ų, and Z = 2. The crystal consists of the heteropolyanion GaW₁₂O ₄₀ ^5– and H⁺ cations. The heteropolyanion GaW₁₂O ₄₀ ^5– is an independent unit and assumed to have the Keggin structure.     

Structure of 2-{2-[3-methyl-3-(2,4,6-trimethylphenyl) cyclobutyl]-2-oxoethyl}isoindole-1,3-dione

2-{2-[3-Methyl-3-(2,4,6-trimethylphenyl)cyclobutyl]-2-oxoethyl}isoindole-1,3-dione (C₂₄ H₂₅NO₃) was synthesized, and its crystal structure was determined by X-ray crystallographic techniques. The compound crystallizes in the triclinic space group P-1, with unit cell parameters: a = 14.109(9) Å, b = 14.130(8) Å, c = 12.152(6) Å, = 105.62(5)°, = 113.75(4)°, = 98.78(5)°, V = 2039.8(19) ų, D _c= 1.223 g/cm³, and Z = 4. The crystal structure has two crystallographically independent molecules, I and II. These molecules are held together by weak intermolecular C—H···O interactions, forming a continuous chain. The dihedral angles between the N-substituted phthalimide moiety and cyclobutane ring in molecules I and II are 60.37(14) and 68.18(18)°, respectively.     

Preparation,spectral studies,and X-ray crystal structures of (16S, 17R, 20S)-3-oxo-16-hydroxy-25-nor-lanostan-24-oic lactone (II) and (16S, 17R, 20S)-4,16-dihydroxy-25-nor-3,4-seco-lanostan-3,24-dioic acid dilactone (III)

The crystal and molecular structures of the title compounds have been determined by direct methods, and refined to a finalR of 0.059 forII and 0.046 forIII. Both molecules crystallize in space group P2₁2₁2₁. The cell dimensions forII area=10.096(5),b=11.255(3),c=20.300(7) Å;Z=4,D _x=1.188 g cm^–3, (MoK)=0.70 cm^–1, while the cell dimensions forIII area=7.346(1),b=10.470(3),c=30.546(5) Å;Z=4,D _x=1.212 g cm^–3, (MoK)=0.74 cm^–1. The rings of the triterpene skeletons aretrans-cis-trans-cis connected. The conformations of both molecules are discussed. Also the preparation and the spectral data of (17R, 20S)-3,16-dioxo-25-nor-lanostan-24-oic acid (V) and (17R, 20S)-3,16,24-trioxo-25-hydroxy-16,24-seco-lanostan-25-acetate (VI) are given.     

An X-ray diffraction study of mesoionic 1-thia-2,3,4-triazolo-5-aminidine and some of its derivatives

X-ray diffraction data are presented for the title mesoionic compound (I), its hydrochloride salt (II) and methylated derivative (III). The crystal of (I) is orthorombic, space group P2₁2₁2₁, with cell dimensions: a = 5.857(1) Å, b = 12.494(2) Å, c = 16.328(3) Å, with four molecules per unit cell. The crystal of (II) is monoclinic, space group P2₁/n, with cell dimensions: a = 5.5720(10) Å, b = 21.5770(4) Å, c = 11.2330(2) Å, beta = 95.15(3)°, with four molecules per unit cell. The crystal of (III) is monoclinic, space group P2₁/n, with cell dimensions: a = 12.0886(5) Å, b = 7.9103(4), c = 104.29(1) Å, beta = 104.29(1)°, with four molecules per unit cell. Of particular interest is the fact that the C5–N6 bond appears to have a high double bond character in all three of the compounds studied. In addition, it is found that the exocyclic N-phenyl group changes from being in the cis conformation with respect to sulfur in compounds (I) and (III) to the trans conformation in the hydrochloric salt (II).