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CRYSTALLOGRAPHIC
COMMUNICATIONS

Volume 77| Part 11

ISSN: 2056-9890

November 2021 issue

Cover illustration: Energetic materials attract a great deal of attention because of their potential applications. At the same time, green approaches to pyrotechnic formulations are gaining interest in the synthesis of new flame colourants. In this contribution, Domasevitch & Ponomarova present the structures of isostrutural Rb and Cs complexes containing a nitro-substituted pyrazol/pyrazolate that exhibit the CsCl topology when considering their ionic networks. Purple and orange coloured flames, respectively, are produced when these cations burn. The crystal engineering approach to the design of these materials will be useful in the synthesis of other polynitro-based energetic compounds. See: Domasevitch & Ponomarova [Acta Cryst. (2021). E77, 1109–1115].

Jerry P. Jasinski tribute

Synthesis and absolute structure of (R)-2-(benzylselanyl)-1-phenylethanaminium hydrogen sulfate monohydrate: crystal structure and Hirshfeld surface analyses

H. R. Rajegowda, P. A. Suchetan, R. J. Butcher and P. Raghavendra Kumar

A hydrogen sulfate salt, [BnSeCH₂CH(Ph)NH₃⁺](HSO₄⁻), of a chiral selenated amine (R)-2-(benzylselanyl)-1-phenylethanamine (BnSeCH₂CH(Ph)NH₂) has been synthesized and characterized by elemental analysis,¹H and ¹³C{¹H} NMR, FT–IR analysis, and single-crystal X-ray diffraction studies. This selenated salt crystallizes as a monohydrate. In the crystal, several O—H⋯O and N—H⋯O hydrogen bonds and C–H⋯π and Se⋯O weak interactions result in a complex two-dimensional sheet-like supramolecular architecture.

CCDC reference: 2114403

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research communications

Synthesis, crystal structure and Hirshfeld surface analysis of (4-methylphenyl)[1-(pentafluorophenyl)-5-(trifluoromethyl)-1H-1,2,3-triazol-4-yl]methanone

N. T. Pokhodylo, Y. Slyvka, E. Goreshnik and R. Lytvyn

The title compound was obtained via the reaction of 1-azido-2,3,4,5,6-pentafluorobenzene with 4,4,4-trifluoro-1-(p-tolyl)butane-1,3-dione using triethylamine as a base catalyst and solvent. In the crystal, the molecules are linked by C—H⋯F and C—H⋯O hydrogen bonds as well as by aromatic π–π stacking interactions into a three-dimensional network.

CCDC reference: 2112438

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Crystal structure and Hirshfeld surface analysis of (3aSR,6RS,6aSR,7RS,11bSR,11cRS)-2,2-dibenzyl-2,3,6a,11c-tetrahydro-1H,6H,7H-3a,6:7,11b-diepoxydibenzo[de,h]isoquinolin-2-ium trifluoromethanesulfonate

Z. Atioğlu, M. Akkurt, G. Z. Mammadova and S. Mlowe

In the crystal, dimeric C—H⋯O hydrogen bonds connect pairs of cations, producing two $[R_{2}^{2}]$ (6) ring motifs parallel to the (001) plane. Intermolecular C—H⋯O hydrogen connections connect the cations and anions, producing a three-dimensional network.

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Crystal structure of methyl 1,3-benzoxazole-2-carboxylate

A. Poirot, N. Saffon-Merceron, N. Leygue, E. Benoist and S. Fery-Forgues

The herringbone structure of methyl 1,3-benzoxazole-2-carboxylate is characterized by strong C—H⋯N and weak C—H⋯O hydrogen bonds, and further stabilized by C—O⋯π and π–π interactions.

CCDC reference: 2112709

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Synthesis and crystal structure of diaquabis(hexamethylenetramine-κN)bis(thiocyanato-κN)cobalt(II)–hexamethylenetetramine–acetonitrile (1/2/2)

C. Krebs, M. Ceglarska and C. Näther

The crystal structure of the title compound consists of discrete neutral complexes in which the cobalt cations are octahedrally coordinated by two N-bonded thiocyanate anions, two hexamethylenetetraamine ligands and two water molecules with additional acetonitrile and hexamethylenetetramine solvate molecules, which are hydrogen bonded to the complexes.

CCDC reference: 2112185

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Crystal structure and Hirshfeld surface analysis of (Z)-2-{[(2,4-dimethylphenyl)imino]methyl}-4-methylphenol

S. Kansiz, A. Gul, N. Dege, E. Agar and E. Saif

The title Schiff base exists in the enol–imine tautomeric form and adopts a Z configuration. In the crystal, the molecules are linked by weak C—H⋯π hydrogen bonds and very weak π–π stacking interactions.

CCDC reference: 2113562

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Crystal structure of 2-oxo-1,2-diphenylethyl diisopropylcarbamate

V. Martens, H. Görls and W. Imhof

The title compound, C₂₁H₂₅NO₃, crystallizes as a racemic twin in the chiral space group P2₁. Both R- and S-enantiomers are connected into infinite helical chains by weak C—H⋯O hydrogen bonds between the phenyl ring of the benzoyl group and the carbamate carbonyl group.

CCDC reference: 2114278

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Crystal structures of two alanylpiperidine analogues

K. Mambourg, N. Tumanov, G. Henon, S. Lanners, J. Garcia-Ladona and J. Wouters

The crystal structures of ethyl 1-[N-(4-methylphenyl)-N-(methylsulfonyl)alanyl]piperidine-4-carboxylate and 1-[N-(4-methylphenyl)-N-(methylsulfonyl)alanyl]piperidine-4-carboxylic acid, two analogues studied as potentiators of Ubiquitin C-terminal hydrolase-L1 (UCH-L1), have been determined. Despite being analogues, different crystal packings are observed. A polymorph risk assessment was carried out to study interactions in the second compound.

CCDC references: 2114340; 2114339

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Formation of a macrocycle from dichlorodimethylsilane and a pyridoxalimine Schiff base ligand

U. Böhme, A. Schwarzer and B. Günther

The reaction of dichlorodimethylsilane with a polydentate Schiff base ligand derived from pyridoxal and 2-ethanolamine yielded a macrocyclic silicon compound.

CCDC reference: 2113407

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Hydrogen-bonding landscape of the carbamoylcyanonitrosomethanide anion in the crystal structure of its ammonium salt

K. V. Domasevitch, G. A. Senchyk, A. B. Lysenko and E. B. Rusanov

The structure of the title salt, ammonium carbamoylcyanonitrosomethanide, NH₄⁺·C₃H₂N₃O₂⁻, features the co-existence of different hydrogen-bonding patterns, which are specific to each of the three functional groups (nitroso, carbamoyl and cyano) of the methanide anion. The relatively simple scheme of these interactions allows the delineation of the supramolecular synthons, which may be applicable to crystal engineering of hydrogen-bonded solids containing polyfunctional methanide anions.

CCDC reference: 2113575

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Isostructural rubidium and caesium 4-(3,5-dinitropyrazol-4-yl)-3,5-dinitropyrazolates: crystal engineering with polynitro energetic species

K. V. Domasevitch and V. V. Ponomarova

In the structures of the title salts, two independent cations (Rb, Cs) are situated on a crystallographic twofold axis and on a center of inversion, respectively. Mutual intermolecular hydrogen bonding between the conjugate 3,5-dinitopyrazole NH-donor and 3,5-dinitropyrazolate N-acceptor sites of the anions governs the self-assembly of the translation-related anions in a predictable fashion. The anionic chains are further linked by multiple ion–dipole interactions involving the 12-coordinate cations bonded to two pyrazole N-atoms and all of the eight nitro O-atoms. The resulting ionic networks follow the CsCl topological archetype, with either metal or organic ions residing in an environment of eight counter-ions. Weak lone pair–π-hole interactions are also relevant to the packing.

CCDC references: 2113578; 2113577

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Synthesis and crystal structure of a new chiral α-aminooxime nickel(II) complex

Y. Homrani, A. Dahdouh, M. A. El Amrani, P. Loxq, F. Capet, I. Suisse and M. Sauthier

The reaction of a nickel precursor with an enantiomerically pure amino-oxime issued from (R)-limonene led to the formation of bis[κ³N,N,N-(aminooxime)-μ-chlorido]dichlorodinickel as a new dinuclear nickel complex.

CCDC reference: 2115017

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Comparison of the crystal structures of the low- and high-temperature forms of bis[4-(dimethylamino)pyridine]dithiocyanatocobalt(II)

C. Krebs, I. Jess and C. Näther

The crystal structures of the low-temperature and the already published high-temperature forms of Co(NCS)₂(DMAP)₂ (DMAP = 4-dimethylaminopyridine) were determined at 100 K, indicating that these two forms represent an exception from the Kitaigorodskii density rule.

CCDC references: 2114553; 2114552

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Crystal structure and Hirshfeld surface analysis of bis[(ethoxymethanethioyl)sulfanido](N,N,N′,N′-tetramethylethane-1,2-diamine)mercury(II)

A. M. Qadir, S. Kansiz, N. Dege and E. Saif

In the crystal, molecules are linked by weak C—H⋯S hydrogen bonds, forming a two-dimensional supramolecular architecture.

CCDC reference: 2115100

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Synthesis and crystal structure of a solvated Co^III complex with 2-hydroxy-3-methoxybenzaldehyde thiosemicarbazone ligands

J. A. Rusanova, V. N. Kokozay, S. Petrusenko and N. Plyuta

The synthesis, crystal structure and spectroscopic characterization of the novel and, according to our knowledge the first to be obtained in crystalline form, Co^III complex with a multidentate NSO-containing mixed-ligand − 2-hydroxy-3-methoxybenzaldehyde thiosemicarbazone – is reported.

CCDC reference: 2115486

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Crystal structure studies of 4-ethylpiperazin-1-ium 3,5-dinitrobenzoate, 4-methylpiperazin-1-ium 3,5-dinitrobenzoate and 4-methylpiperazin-1-ium 4-iodobenzoate

S. D. Archana, H. K. Kumar, H. S. Yathirajan, S. Foro, M. S. M. Abdelbaky and S. Garcia-Granda

Three novel piperazinium salts are described. Their crystal structure is based on layers formed by hydrogen bonding, halogen bonding and other weak interactions. One exhibits an asymmetric unit containing a 1-ethylpiperazinium cation and a 3,5-dinitrobenzoate anion while the other two salts have asymmetric units containing 1-methylpiperazinium as a common cation and a 3,5-dinitrobenzoate anion or a 4-iodobenzoate anion.

CCDC references: 2115865; 2115864; 2115863

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Crystal structure of [{[Ni(C₁₀H₂₄N₄)][Ni(CN)₄]}·2H₂O]_n, a one-dimensional coordination polymer formed from the [Ni(cyclam)]²⁺ cation and the [Ni(CN)₄]^2– anion

L. V. Tsymbal, I. L. Andriichuk, S. Shova and Y. D. Lampeka

The title coordination polymer consists of parallel linear chains built up of macrocyclic cations possessing a slightly tetragonally distorted NiN₆ octahedral coordination geometry formed by four N atoms of the azamacrocyclic ligand in the equatorial plane and two trans N atoms of the cyanide groups of the bridging tetracyanonickelate anion in the axial positions. In the crystal, two independent [1 $[\overline{1}]$ 0] polymeric chains are cross-linked by N—H⋯O_w (w = water) and O_w—H⋯N_c (c = cyanide) hydrogen bonds into a three-dimensional network.

CCDC reference: 2114932

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Role of pK_a in establishing the crystal structures of six hydrogen-bonded compounds of 4-methylquinoline with different isomers of chloro- and nitro-substituted benzoic acids

H. Ishida

The structures of the six hydrogen-bonded 1:1 compounds of 4-methylquinoline with 2-chloro-4-nitrobenzoic acid, 2-chloro-5-nitrobenzoic acid, 2-chloro-6-nitrobenzoic acid, 3-chloro-2-nitrobenzoic acid, 4-chloro-2-nitrobenzoic acid and 5-chloro-2-nitrobenzoic acid have been determined at 185–190 K. In each crystal, the acid and base molecules are linked by a short hydrogen bond between a carboxy/carboxylate O atom and an N atom of the base.

CCDC references: 2116680; 2116679; 2116678; 2116677; 2116676; 2116675

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Crystal structure and Hirshfeld surface analysis of di-μ-chlorido-bis[(acetonitrile-κN)chlorido(ethyl 5-methyl-1H-pyrazole-3-carboxylate-κ²N²,O)copper(II)]

O. S. Vynohradov, V. A. Pavlenko, O. I. Kucheriv, I. A. Golenya, D. Petlovanyi and S. Shova

The title compound, [Cu₂Cl₄(C₅H₁₀N₂O₂)₂(CH₃CN)₂] or [Cu₂(μ₂-Cl)₂(CH₃—Pz-COOCH₂CH₃)₂Cl₂(CH₃CN)₂], was synthesized using an one-pot reaction of copper powder, copper(II) chloride dihydrate and ethyl 5-methyl-1H-pyrazole-3-carboxylate (CH₃—Pz-COOCH₂CH₃) in acetonitrile under ambient conditions. This complex consists of discrete binuclear molecules with a {Cu₂(μ₂-Cl)₂} core.

CCDC reference: 2115608

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Crystal structure and Hirshfeld surface analysis of (E)-1-[2,2-dichloro-1-(4-fluorophenyl)ethenyl]-2-(2,4-dichlorophenyl)diazene

N. Q. Shikhaliyev, K. Özkaraca, M. Akkurt, X. N. Bagirova, G. T. Suleymanova, M. S. Abdulov and S. Mlowe

In the crystal, C—H⋯N, C—Cl⋯π interactions and face-to-face π–π stacking interactions connect the molecules, forming ribbons along the a-axis direction.

CCDC reference: 2116300

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Crystal structure, Hirshfeld surface analysis and DFT studies of tetrakis(μ-3-nitrobenzoato-κ²O¹:O^1′)bis[(N,N-dimethylformamide-κO)copper(II)] dimethylformamide disolvate

M. A. Ziyaev, J. M. Ashurov, A. G. Eshimbetov and B. T. Ibragimov

The title compound, [Cu₂(C₇H₄NO₄)₄(C₃H₇NO)₂]·(C₃H₇NO)₂, is a binuclear copper(II) complex located on an inversion center midway between the two copper(II) cations. The asymmetric unit consists of one Cu^II cation, two 3-nitrobenzoato ligands, and two dimethylformamide (DMF) molecules, one of which coordinates to the Cu^II cation and one is a solvate molecule. The carboxylate groups of the ligands bridge two Cu^II cations, completing a distorted octahedral O₅Cu coordination environment.

CCDC reference: 2036680

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Crystal structure, Hirshfeld surface and frontier molecular orbital analysis of 9-(3-bromo-4-hydroxy-5-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione

N. Suresh Babu, V. Sughanya, D. Praveenkumar and M. L. Sundararajan

In the xanthene moiety of the title compound, the central ring adopts a flattened-boat conformation whereas the cyclohexenone rings adopt envelope conformations. In the crystal, molecules are linked by pairs of O—H⋯O hydrogen bonds, forming inversion dimers with an $[R_{2}^{2}]$ (20) ring motif.

CCDC reference: 2064558

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Crystal structure of trans-diaqua(1,4,8,11-tetraazaundecane)nickel(II) bis(pyridine-2,6-dicarboxylato)nickel(II)

I. L. Andriichuk, L. V. Tsymbal, V. B. Arion and Y. D. Lampeka

The coordination polyhedra of the nickel(II) ions of the title compound in the complex cation and the anion, viz., trans-NiN₄O₂ and trans-NiO₄N₂, are distorted octahedra. In the crystal, the donor groups of the tetraamine and the coordinated water molecules and the carboxylate groups of the pyridine-2,6-dicarboxylate anions are involved in numerous N—H⋯O and O—H⋯O hydrogen bonds, thereby forming sheets of ions lying parallel to the (001) plane.

CCDC reference: 2115829

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Syntheses and crystal structures of two copper(I)–halide π,σ-coordination compounds based on 2-[(prop-2-en-1-yl)sulfanyl]pyridine

Y. Slyvka, N. T. Pokhodylo, E. Goreshnik, O. Pavlyuk and M. Mys'kiv

The title compounds, di-μ-chlorido-bis({2-[(η-2,3)-(prop-2-en-1-yl)sulfanyl]pyridine-κN}copper(I)) and di-μ-bromido-bis({2-[(η-2,3)-(prop-2-en-1-yl)sulfanyl]pyridine-κN}copper(I)) were obtained by alternating-current electrochemical synthesis starting from an ethanolic solution of 2-[(prop-2-en-1-yl)sulfanyl]pyridine (Psup) and the copper(II) halide. The isostructural crystals are built up from centrosymmetric [Cu₂Hal₂(Psup)₂] dimers, which are formed due to the π,σ-chelating behavior of the organic ligand.

CCDC references: 2116969; 2116968

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Crystal structures of Zn(cyclam)I₂ (second monoclinic polymorph) and Zn(cyclam)I(I₃)

S. P. Gavrish, S. Shova and Y. D. Lampeka

The crystal of the first title compound contains five-coordinate [Zn(L)I]⁺ (L = cyclam) cations and non-coordinated iodide anions; the extended structure is consolidated by N—H⋯I and N—H⋯(I,I) hydrogen bonds. The crystals of the second title compound consist of chains of [Zn(L)I]⁺ units and triiodide counter-ions but without significant hydrogen-bonding interactions.

CCDC references: 2115387; 2115388

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issue contents

November 2021 issue

Jerry P. Jasinski tribute

Synthesis and absolute structure of (R)-2-(benzylselanyl)-1-phenylethanaminium hydrogen sulfate monohydrate: crystal structure and Hirshfeld surface analyses

research communications

Synthesis, crystal structure and Hirshfeld surface analysis of (4-methylphenyl)[1-(pentafluorophenyl)-5-(trifluoromethyl)-1H-1,2,3-triazol-4-yl]methanone

Crystal structure and Hirshfeld surface analysis of (3aSR,6RS,6aSR,7RS,11bSR,11cRS)-2,2-dibenzyl-2,3,6a,11c-tetrahydro-1H,6H,7H-3a,6:7,11b-diepoxydibenzo[de,h]isoquinolin-2-ium trifluoromethanesulfonate

Crystal structure of methyl 1,3-benzoxazole-2-carboxylate

Synthesis and crystal structure of diaquabis(hexamethylenetramine-κN)bis(thiocyanato-κN)cobalt(II)–hexamethylenetetramine–acetonitrile (1/2/2)

Crystal structure and Hirshfeld surface analysis of (Z)-2-{[(2,4-dimethylphenyl)imino]methyl}-4-methylphenol

Crystal structure of 2-oxo-1,2-diphenylethyl diisopropylcarbamate

Crystal structures of two alanylpiperidine analogues

Formation of a macrocycle from dichlorodimethylsilane and a pyridoxalimine Schiff base ligand

Hydrogen-bonding landscape of the carbamoylcyanonitrosomethanide anion in the crystal structure of its ammonium salt

Isostructural rubidium and caesium 4-(3,5-dinitropyrazol-4-yl)-3,5-dinitropyrazolates: crystal engineering with polynitro energetic species

Synthesis and crystal structure of a new chiral α-aminooxime nickel(II) complex

Comparison of the crystal structures of the low- and high-temperature forms of bis[4-(dimethylamino)pyridine]dithiocyanatocobalt(II)

Crystal structure and Hirshfeld surface analysis of bis[(ethoxymethanethioyl)sulfanido](N,N,N′,N′-tetramethylethane-1,2-diamine)mercury(II)

Synthesis and crystal structure of a solvated Co^III complex with 2-hydroxy-3-methoxybenzaldehyde thiosemicarbazone ligands

Crystal structure studies of 4-ethylpiperazin-1-ium 3,5-dinitrobenzoate, 4-methylpiperazin-1-ium 3,5-dinitrobenzoate and 4-methylpiperazin-1-ium 4-iodobenzoate

Crystal structure of [{[Ni(C₁₀H₂₄N₄)][Ni(CN)₄]}·2H₂O]_n, a one-dimensional coordination polymer formed from the [Ni(cyclam)]²⁺ cation and the [Ni(CN)₄]^2– anion

Role of pK_a in establishing the crystal structures of six hydrogen-bonded compounds of 4-methylquinoline with different isomers of chloro- and nitro-substituted benzoic acids

Crystal structure and Hirshfeld surface analysis of di-μ-chlorido-bis[(acetonitrile-κN)chlorido(ethyl 5-methyl-1H-pyrazole-3-carboxylate-κ²N²,O)copper(II)]

Crystal structure and Hirshfeld surface analysis of (E)-1-[2,2-dichloro-1-(4-fluorophenyl)ethenyl]-2-(2,4-dichlorophenyl)diazene

Crystal structure, Hirshfeld surface analysis and DFT studies of tetrakis(μ-3-nitrobenzoato-κ²O¹:O^1′)bis[(N,N-dimethylformamide-κO)copper(II)] dimethylformamide disolvate

Crystal structure, Hirshfeld surface and frontier molecular orbital analysis of 9-(3-bromo-4-hydroxy-5-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione

Crystal structure of trans-diaqua(1,4,8,11-tetraazaundecane)nickel(II) bis(pyridine-2,6-dicarboxylato)nickel(II)

Syntheses and crystal structures of two copper(I)–halide π,σ-coordination compounds based on 2-[(prop-2-en-1-yl)sulfanyl]pyridine

Crystal structures of Zn(cyclam)I₂ (second monoclinic polymorph) and Zn(cyclam)I(I₃)

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