MyMedR

Fulltext Design, synthesis and cytotoxic effects of curcuminoids on HeLa, K562, MCF-7 and MDA-MB-231 cancer cell lines

Zamrus SNH, Akhtar MN, Yeap SK, Quah CK, Loh WS, Alitheen NB, et al.

Chem Cent J, 2018 Mar 19;12(1):31.

PMID: 29556774 DOI: 10.1186/s13065-018-0398-1

BACKGROUND: Curcumin is one of the leading compound extracted from the dry powder of Curcuma longa (Zingiberaceae family), which possess several pharmacological properties. However, in vivo administration exhibited limited applications in cancer therapies.

RESULTS: Twenty-four curcumin derivatives have synthesized, which comprises cyclohexanone 1-10, acetone 11-17 and cyclopentanone 18-24 series. All the curcuminoids were synthesized by the acid or base catalyzed Claisen Schmidt condenstion reactions, in which β-diketone moiety of curcumin was modified with mono-ketone. These curcuminoids 1-24 were screened against HeLa, K562, MCF-7 (an estrogen-dependent) and MDA-MB-231 (an estrogen-independent) cancer cell lines. Among them, acetone series 11-17 were found to be more selective and potential cytotoxic agents. The compound 14 was exhibited (IC50 = 3.02 ± 1.20 and 1.52 ± 0.60 µg/mL) against MCF-7 and MDA-MB-231 breast cancer cell lines. Among the cyclohexanone series, the compound 4 exhibited (IC50 = 11.04 ± 2.80, 6.50 ± 01.80, 8.70 ± 3.10 and 2.30 ± 1.60 µg/mL) potential cytotoxicity against four proposed cancer cell lines, respectively. All the curcucminoids were characterized with the detailed1H NMR, IR, UV-Vis, and mass spectroscopic techniques. The structure of compound 4 was confirmed by using the single X-ray crystallography. Additionally, we are going to report the first time spectral data of (2E,6E)-2,6-bis(2-methoxybenzylidene)cyclohexanone (1). Structure-activity relationships revealed that the mono-carbonyl with 2,5-dimethoxy substituted curcuminoids could be an essential for the future drugs against cancer diseases.

CONCLUSIONS: Curcuminoids with diferuloyl(4-hydroxy-3-methoxycinnamoyl) moiety with mono carbonyl exhibiting potential cytotoxic properties. The compound 14 was exhibited (IC50 = 3.02 ± 1.20 and 1.52 ± 0.60 µg/mL) against MCF-7 and MDA-MB-231 breast cancer cell lines.

Fulltext Crystal structure and Hirshfeld surface analysis of a chalcone derivative: (E)-3-(4-fluoro-phen-yl)-1-(4-nitro-phen-yl)prop-2-en-1-one

Wong QA, Chia TS, Kwong HC, Chidan Kumar CS, Quah CK, Arafath MA

Acta Crystallogr E Crystallogr Commun, 2019 Jan 01;75(Pt 1):53-57.

PMID: 30713733 DOI: 10.1107/S2056989018017450

The mol-ecular structure of the title chalcone derivative, C15H10FNO3, is nearly planar and the mol-ecule adopts a trans configuration with respect to the C=C double bond. The nitro group is nearly coplanar with the attached benzene ring, which is nearly parallel to the second benzene ring. In the crystal, mol-ecules are connected by pairs of weak inter-molecular C-H⋯O hydrogen bonds into inversion dimers. The dimers are further linked by another C-H⋯O hydrogen bond and a C-H⋯F hydrogen bond into sheets parallel to (104). π-π inter-actions occur between the sheets, with a centroid-centroid distance of 3.8860 (11) Å. Hirshfeld surface analysis was used to investigate and qu-antify the inter-molecular inter-actions.

Crystal structure, vibrational spectra and DFT simulations of 2-fluoro-4-bromobenzaldehyde

Tursun M, Kumar CS, Bilge M, Rhyman L, Fun HK, Parlak C, et al.

Spectrochim Acta A Mol Biomol Spectrosc, 2015 Jul 5;146:342-9.

PMID: 25829021 DOI: 10.1016/j.saa.2015.03.022

Molecular structure and properties of 2-fluoro-4-bromobenzaldehyde (FBB, C7H4BrFO) was experimentally investigated by X-ray diffraction technique and vibrational spectroscopy. Experimental results on the molecular structure of FBB were supported with computational studies using the density functional theory, with the Becke-3-Lee-Yang-Parr functional and the 6-311+G(3df,p) basis set. Molecular dimer formed by the intermolecular hydrogen bonding was investigated. Potential energy distribution analysis of normal modes was performed to identify characteristic frequencies. FBB crystallizes in orthorhombic space group P2(1)2(1)2(1) with the O-trans conformation. In order to investigate halogen effect, the chloro- (CBB) and bromo- (BBB) analogs of FBB have also been studied theoretically. It is observed that all compounds prefer the stable O-trans conformation. Although the free energy difference between the O-cis and O-trans conformers is less than 2.5 kcal/mol, the free energy rotational barrier is at least 7.4 kcal/mol. There is a good agreement between the experimentally determined structural parameters, and vibrational frequencies of FBB and those predicted theoretically.

Then LY, Chidan Kumar CS, Kwong HC, Win YF, Mah SH, Quah CK, et al.

Acta Crystallogr E Crystallogr Commun, 2017 Jul 01;73(Pt 7):1087-1091.

PMID: 28775889 DOI: 10.1107/S2056989017009422

The compounds 2-(1-benzo-furan-2-yl)-2-oxoethyl 2-nitro-benzoate, C17H11NO6 (I), and 2-(1-benzo-furan-2-yl)-2-oxoethyl 2-amino-benzoate, C17H13NO4 (II), were synthesized under mild conditions. Their mol-ecular structures were characterized by both spectroscopic and single-crystal X-ray diffraction analysis. The mol-ecular conformations of both title compounds are generally similar. However, different ortho-substituted moieties at the phenyl ring of the two compounds cause deviations in the torsion angles between the carbonyl group and the attached phenyl ring. In compound (I), the ortho-nitro-phenyl ring is twisted away from the adjacent carbonyl group whereas in compound (II), the ortho-amino-phenyl ring is almost co-planar with the carbonyl group. In the crystal of compound (I), two C-H⋯O hydrogen bonds link the mol-ecules into chains propagating along the c-axis direction and the chains are inter-digitated, forming sheets parallel to [20-1]. Conversely, pairs of N-H⋯O hydrogen bonds in compound (II) link inversion-related mol-ecules into dimers, which are further extended by C-H⋯O hydrogen bonds into dimer chains. These chains are inter-connected by π-π inter-actions involving the furan rings, forming sheets parallel to the ac plane.

Fulltext Steric repulsion and supra-molecular assemblies via a two-dimensional plate by C-H⋯O hydrogen bonds in two closely related 2-(benzo-furan-2-yl)-2-oxoethyl benzoates

Then LY, Chidan Kumar CS, Kwong HC, Win YF, Mah SH, Quah CK, et al.

Acta Crystallogr E Crystallogr Commun, 2017 Jul 01;73(Pt 8):1227-1231.

PMID: 28932442 DOI: 10.1107/S2056989017010556

2-(Benzo-furan-2-yl)-2-oxoethyl 2-chloro-benzoate, C17H11ClO4 (I), and 2-(benzo-furan-2-yl)-2-oxoethyl 2-meth-oxy-benzoate, C18H14O5 (II), were synthesized under mild conditions. Their chemical and mol-ecular structures were analyzed by spectroscopic and single-crystal X-ray diffraction studies, respectively. These compounds possess different ortho-substituted functional groups on their phenyl rings, thus experiencing extra steric repulsion force within their mol-ecules as the substituent changes from 2-chloro (I) to 2-meth-oxy (II). The crystal packing of compound (I) depends on weak inter-molecular hydrogen bonds and π-π inter-actions. Mol-ecules are related by inversion into centrosymmetric dimers via C-H⋯O hydrogen bonds, and further strengthened by π-π inter-actions between furan rings. Conversely, mol-ecules in compound (II) are linked into alternating dimeric chains propagating along the [101] direction, which develop into a two-dimensional plate through extensive inter-molecular hydrogen bonds. These plates are further stabilized by π-π and C-H⋯π inter-actions.

Fulltext 6-(4-Amino-phen-yl)-2-meth-oxy-4-phenyl-nicotino-nitrile

Suwunwong T, Chantrapromma S, Quah CK, Fun HK

Acta Crystallogr Sect E Struct Rep Online, 2013 Nov 23;69(Pt 12):o1816-7.

PMID: 24454245 DOI: 10.1107/S1600536813031437

In the structure of the title nicotino-nitrile derivative, C19H15N3O, the pyridine ring makes dihedral angles of 11.50 (7) and 43.36 (8)° with the 4-amino-phenyl and phenyl rings, respectively, and the dihedral angle between the phenyl rings is 36.28°. In the crystal, mol-ecules are linked by N-H⋯N hydrogen bonds into wave-like sheets parallel to (10-2). These sheets are stacked by π-π inter-actions between the 4-amino-phenyl rings of adjacent sheets, with centroid-centroid distances of 3.7499 (9) Å. C-H⋯π inter-actions are also present.

Fulltext Three closely related (2E,2'E)-3,3'-(1,4-phenyl-ene)bis-[1-(meth-oxy-phen-yl)prop-2-en-1-ones]: supra-molecular assemblies in one dimension mediated by hydrogen bonding and C-H⋯π inter-actions

Sim A, Chidan Kumar CS, Kwong HC, Then LY, Win YF, Quah CK, et al.

Acta Crystallogr E Crystallogr Commun, 2017 Jun 01;73(Pt 6):896-900.

PMID: 28638654 DOI: 10.1107/S2056989017007460

In the title compounds, (2E,2'E)-3,3'-(1,4-phenyl-ene)bis-[1-(2-meth-oxy-phen-yl)prop-2-en-1-one], C26H22O4 (I), (2E,2'E)-3,3'-(1,4-phenyl-ene)bis-[1-(3-meth-oxy-phen-yl)prop-2-en-1-one], C26H22O4 (II) and (2E,2'E)-3,3'-(1,4-phenyl-ene)bis-[1-(3,4-di-meth-oxy-phen-yl)prop-2-en-1-one], C28H26O6 (III), the asymmetric unit consists of a half-mol-ecule, completed by crystallographic inversion symmetry. The dihedral angles between the central and terminal benzene rings are 56.98 (8), 7.74 (7) and 7.73 (7)° for (I), (II) and (III), respectively. In the crystal of (I), mol-ecules are linked by pairs of C-H⋯π inter-actions into chains running parallel to [101]. The packing for (II) and (III), features inversion dimers linked by pairs of C-H⋯O hydrogen bonds, forming R2(2)(16) and R2(2)(14) ring motifs, respectively, as parts of [201] and [101] chains, respectively.

Fulltext Crystal structure and Hirshfeld surface analysis of (2E)-3-(3-chloro-phen-yl)-1-(3,4-di-meth-oxy-phen-yl)prop-2-en-1-one

Sheshadri SN, Atioğlu Z, Akkurt M, Chidan Kumar CS, Quah CK, Siddaraju BP, et al.

Acta Crystallogr E Crystallogr Commun, 2018 Jul 01;74(Pt 7):935-938.

PMID: 30002889 DOI: 10.1107/S205698901800837X

In title compound, C17H15ClO3, the dihedral angle between the benzene and chloro-phenyl rings is 18.46 (7)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen contacts, enclosing an R22(14) ring motif, and by a further C-H⋯O hydrogen contact, forming a two-dimensional supra-molecular structure extending along the direction parallel to the ac plane. Hirshfeld surface analysis shows that van der Waals inter-actions constitute the major contribution to the inter-molecular inter-actions, with H⋯H contacts accounting for 36.2% of the surface.

Fulltext Crystal structure and Hirshfeld surface analysis of a pyridiniminium bromide salt: 1-[2-([1,1'-biphen-yl]-4-yl)-2-oxoeth-yl]-3-methyl-1,4-di-hydro-pyridin-4-iminium bromide

Sheshadri SN, Kwong HC, Chidan Kumar CS, Quah CK, Siddaraju BP, Veeraiah MK, et al.

Acta Crystallogr E Crystallogr Commun, 2018 May 01;74(Pt 5):752-756.

PMID: 29850106 DOI: 10.1107/S2056989018006217

In the cation of the title salt, C20H19N2O+·Br-, the phenyl rings are inclined to one another by 38.38 (8)°, whereas the central phenyl ring and the pyridiniminium ring are almost perpendicular with a dihedral angle of 87.37 (9)°. The N+=C cationic double bond was verified by the shortened bond length of 1.337 (2) Å. In the crystal, the Br- anion is linked to the cation by an N-H⋯Br hydrogen bond. C-H⋯O hydrogen bonds link adjacent pyridiniminium cations into inversion dimers with an R22(18) graph-set motif. These dimers are stacked in a phen-yl-phenyl T-shaped geometry through C-H⋯π inter-actions. A Hirshfeld surface analysis was conducted to verify the contributions of the different inter-molecular inter-actions.

Fulltext Crystal structure and Hirshfeld surface analysis of (2E)-3-(3-bromo-4-fluoro-phen-yl)-1-(3,4-di-meth-oxy-phen-yl)prop-2-en-1-one

Sheshadri SN, Atioğlu Z, Akkurt M, Veeraiah MK, Quah CK, Chidan Kumar CS, et al.

Acta Crystallogr E Crystallogr Commun, 2018 Aug 01;74(Pt 8):1063-1066.

PMID: 30116562 DOI: 10.1107/S2056989018009416

In the mol-ecule of the title compound, C17H14BrFO3, the aromatic rings are tilted with respect to the enone bridge by 13.63 (14) and 4.27 (15)°, and form a dihedral angle 17.91 (17)°. In the crystal, centrosymmetrically related mol-ecules are linked by pairs of C-H⋯O hydrogen bonds into dimeric units, forming rings of R22(14) graph-set motif. The dimers are further connected by weak C-H⋯O hydrogen inter-actions, forming layers parallel to (10). Hirshfeld surface analysis shows that van der Waals inter-actions constitute the major contribution to the inter-molecular inter-actions, with H⋯H contacts accounting for 29.7% of the surface.

Fulltext Crystal structure and Hirshfeld surface analysis of (E)-3-(2-chloro-4-fluoro-phen-yl)-1-(2,5-di-chloro-thio-phen-3-yl)prop-2-en-1-one

Sanjeeva Murthy TN, Naveen S, Chidan Kumar CS, Veeraiah MK, Quah CK, Siddaraju BP, et al.

Acta Crystallogr E Crystallogr Commun, 2018 Aug 01;74(Pt 8):1134-1137.

PMID: 30116578 DOI: 10.1107/S2056989018010216

In the title chalcone-thio-phene derivative, C13H6Cl3FOS, the aromatic rings are inclined to one another by 12.9 (2)°, and the thio-phene ring is affected by π-conjugation. In the crystal, mol-ecules are linked by C-H⋯F hydrogen bonds, forming an R22(8) ring motif. A Hirshfeld surface analysis was conducted to verify the contribution of the different inter-molecular inter-actions. The shape-index surface clearly shows that the two sides of the mol-ecules are involved in the same contacts with neighbouring mol-ecules and the curvedness plots show flat surface patches characteristic of planar stacking.

New2-((2-(2,4-dinitrophenyl)hydrazineeylidene) derivatives: design, synthesis, in silico, and in vitro anticancer studies

Sajjan VP, Anigol LB, Gurubasavaraj PM, Patil D, Patil PS, Gummagol NB, et al.

J Biomol Struct Dyn, 2023;41(21):11681-11699.

PMID: 36602778 DOI: 10.1080/07391102.2022.2163424

A series of novel hydrazone compounds have been synthesized by the condensation of hydrazines and different substituted salicylaldehydes at a molar ratio of 1:1 in one step reaction and characterized by FT-IR, ESI-MS, 1H NMR, and single crystal x-ray diffraction. The crystal structure of the compound shows a trans configuration around the C = N bond and triclinic system with P -1/-p 1. Synthesized compounds were screened for cytotoxicity activities against A375 (melanoma), HT-29 (Colon), and A549 (lung) cancer cell lines. Among them, compound 2 exhibited the highest cytotoxic effect against the A375 cell line (IC50 = 0.30 µM) and HT-29 cell line (1.68 µM), compared to those of apatinib as a reference standard drug (0.28, 1.49 µM, respectively). The cytocompatibility assay on the L929 normal cell line and the hemolysis assay on human RBC were used to validate the non-toxic action. From DFT calculation, the various parameters such as HOMO-LUMO energies, Hirshfeld, and MEP have been studied. Furthermore, in silico molecular docking with three receptors was studied. Among four compounds, compound 2 has the lowest binding energy against cyclin dependent kinase (ΔGb = -9.3 kcal/mol). In addition to this, molecular dynamics (MD) simulation was also performed. Based on this study, these novel hydrazones can be considered a promising anticancer agent due to their potent cytotoxicity activities and computational analysis.Communicated by Ramaswamy H. Sarma.

Fulltext 6-(Hex-5-en-yloxy)naphthalene-2-carb-oxy-lic acid

Rahman ML, Srinivasa HT, Mohd Yusoff M, Kwong HC, Quah CK

Acta Crystallogr Sect E Struct Rep Online, 2014 Jun 1;70(Pt 6):o696-7.

PMID: 24940271 DOI: 10.1107/S1600536814010642

The asymmetric unit of the title compound, C17H18O3, comprises three independent mol-ecules with similar geometries. In each mol-ecule, the carbonyl group is twisted away from the napthalene ring system, making dihedral angles of 1.0 (2), 1.05 (19)° and 1.5 (2)°. The butene group in all three mol-ecules are disordered over two sets of sites, with a refined occupancy ratio of 0.664 (6):0.336 (6). In the crystal, mol-ecules are oriented with respect to their carbonyl groups, forming head-to-head dimers via O-H⋯O hydrogen bonds. Adjacent dimers are further inter-connected by C-H⋯O hydrogen bonds into chains along the a-axis direction. The crystal structure is further stabilized by weak C-H⋯π inter-actions.

Fulltext 6-Cyanona-phthalen-2-yl 4-hexyl-benzo-ate

Rahman ML, Srinivasa HT, Mashitah MY, Kwong HC, Quah CK

Acta Crystallogr Sect E Struct Rep Online, 2014 May 1;70(Pt 5):o620.

PMID: 24860410 DOI: 10.1107/S160053681400909X

In the title compound, C24H23NO2, a whole mol-ecule is disordered over two sets of sites with occupancies in a ratio of 0.692 (6):0.308 (6). In the major disorder component, the naphthalene ring system forms a dihedral angle of 68.6 (5)° with the benzene ring. The corresponding angle in the minor component is 81.6 (10)°. In the crystal, mol-ecules are linked into chains propagating along the b-axis direction via weak C-H⋯O hydrogen bonds. The crystal packing is further consolidated by weak C-H⋯π inter-actions.

Fulltext Crystal structure of (E)-4-{2-[4-(all-yloxy)phen-yl]diazen-yl}benzoic acid

Rahman ML, Mohd Yusoff M, Ismail J, Kwong HC, Quah CK

Acta Crystallogr Sect E Struct Rep Online, 2014 Dec 01;70(Pt 12):499-502.

PMID: 25552976 DOI: 10.1107/S1600536814023745

The title compound, C16H14N2O3, has an E conformation about the azo-benzene [-N=N- = 1.2481 (16) Å] linkage. The benzene rings are almost coplanar [dihedral angle = 1.36 (7)°]. The O atoms of the carb-oxy-lic acid group are disordered over two sets of sites and were refined with an occupancy ratio of 0.5:0.5. The two disordered components of the carb-oxy-lic acid group make dihedral angles of 1.5 (14) and 3.8 (12)° with the benzene ring to which they are attached. In the crystal, mol-ecules are linked via pairs of O-H⋯O hydrogen bonds, forming inversion dimers. The dimers are connected via C-H⋯O hydrogen bonds, forming ribbons lying parallel to [120]. These ribbons are linked via C-H⋯π inter-actions, forming slabs parallel to (001).

Fulltext Crystal structure of 3-{5-[3-(4-fluoro-phen-yl)-1-isopropyl-1H-indol-2-yl]-1H-pyrazol-1-yl}indolin-2-one ethanol monosolvate

Rahman ML, Kulkarni AD, Mohd Yusoff M, Kwong HC, Quah CK

Acta Crystallogr E Crystallogr Commun, 2016 Mar 01;72(Pt 3):283-6.

PMID: 27006787 DOI: 10.1107/S2056989016001614

The title indolin-2-one compound, C28H23FN4O·C2H6O, crystallizes as a 1:1 ethanol solvate. The ethanol mol-ecule is disordered over two positions with refined site occupancies of 0.560 (14) and 0.440 (14). The pyrazole ring makes dihedral angles of 84.16 (10) and 85.33 (9)° with the indolin-2-one and indole rings, respectively, whereas the dihedral angle between indolin-2-one and indole rings is 57.30 (7)°. In the crystal, the components are linked by N-H⋯O and O-H⋯O hydrogen bonds, forming an inversion mol-ecule-solvate 2:2 dimer with R 4 (4)(12) ring motifs. The crystal structure is consolidated by π-π inter-action between pairs of inversion-related indolin-2-one rings [inter-planar spacing = 3.599 (2) Å].

Fulltext 3-(4-Chloro-phen-yl)-5-(4-eth-oxy-phen-yl)-4,5-dihydro-1H-pyrazole-1-carbothio-amide ethanol monosolvate

Quah CK, Fun HK, Suwunwong T, Boonnak N, Chantrapromma S

Acta Crystallogr Sect E Struct Rep Online, 2013 Apr 1;69(Pt 4):o464-5.

PMID: 23634024 DOI: 10.1107/S1600536813005369

The asymmetric unit of the title compound, C18H18ClN3OS·C2H5OH, comprises a pyrazoline derivative and an ethanol solvent mol-ecule. In the mol-ecule of the pyrazoline derivative, the pyrazole ring adopts an envelope conformation with the C atom bearing the eth-oxy-phenyl substituent as the flap. The dihedral angle between the benzene rings is 74.22 (7)°. The eth-oxy group is coplanar with the attached benzene ring [C-O-C-Cmeth-yl = 175.50 (11)° and r.m.s. deviation = 0.0459 (1) Å for the nine non-H atoms]. In the crystal, the pyrazoline mol-ecules are linked by N-H⋯Oeth-oxy hydrogen bonds into chains along the c axis and are further linked with the solvent ethanol mol-ecules by N-H⋯Oethanol and Oethanol-H⋯S hydrogen bonds. C-H⋯π inter-actions are also present.

Fulltext 2-Amino-5-bromo-pyridine-4-hy-droxy-benzoic acid (1/1)

Quah CK, Hemamalini M, Fun HK

Acta Crystallogr Sect E Struct Rep Online, 2010;66(Pt 8):o1935-6.

PMID: 21588263 DOI: 10.1107/S1600536810025924

The title 1:1 adduct, C(5)H(5)BrN(2)·C(7)H(6)O(3), contains two mol-ecules of each species in the asymmetric unit, with similar geometries. In the crystal, mol-ecules are linked to form extended chains along [100] by N-H⋯O, O-H⋯O, O-H⋯N and C-H⋯O hydrogen bonds. Adjacent chains are crosslinked via further N-H⋯O inter-actions into sheets lying parallel to (001). The crystal studied was an inversion twin with a 0.54 (2):0.46 (2) domain ratio.

Fulltext 2-Amino-4-methylpyridinium 2-hy-droxy-3,5-dinitro-benzoate

Quah CK, Hemamalini M, Fun HK

Acta Crystallogr Sect E Struct Rep Online, 2010;66(Pt 8):o1933-4.

PMID: 21588262 DOI: 10.1107/S1600536810025912

In the anion of the title mol-ecular salt, C(6)H(9)N(2) (+)·C(7)H(3)N(2)O(7) (-), the two nitro groups are twisted from the attached benzene ring with dihedral angles of 27.36 (10) and 4.86 (11)°. The anion is stabilized by an intra-molecular O-H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, the cations and anions are linked by N-H⋯O and C-H⋯O inter-actions and are further consolidated by C-H⋯π inter-actions, to generate a three-dimensional network. A short O⋯N contact of 2.876 (2) Å also occurs.

Fulltext 2-Amino-4-methyl-pyridinium 2-carb-oxy-benzoate

Quah CK, Hemamalini M, Fun HK

Acta Crystallogr Sect E Struct Rep Online, 2010;66(Pt 8):o1932.

PMID: 21588261 DOI: 10.1107/S1600536810025900

In the title mol-ecular salt, C(6)H(9)N(2) (+)·C(8)H(5)O(4) (-), the anion is stabilized by an intra-molecular O-H⋯O hydrogen bond, which generates an S(7) ring motif. In the crystal, the cations and anions are linked to form extended chains along [001] by O-H⋯O and N-H⋯O hydrogen bonds. Adjacent chains are crosslinked via C-H⋯O inter-actions into sheets lying parallel to (100).

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