The synthesis and structural characterization of three families of coordination com­plexes synthesized from 4'-phenyl-2,2':6',2''-terpyridine (8, Ph-TPY), 4'-(4-chloro­phen­yl)-2,2':6',2''-terpyridine (9, ClPh-TPY) and 4'-(4-meth­oxy­phen­yl)-2,2':6',2''-terpyridine (10, MeOPh-TPY) ligands with the divalent metals Co2+, Fe2+, Mn2+ and Ni2+ are reported. The com­pounds were synthesized from a 1:2 mixture of the metal and ligand, resulting in a series of com­plexes with the general formula [M(R-TPY)2](ClO4)2 (where M = Co2+, Fe2+, Mn2+ and Ni2+, and R-TPY = Ph-TPY, ClPh-TPY and MeOPh-TPY). The general formula and structural and supra­molecular features were determinated by single-crystal X-ray diffraction for bis­(4'-phenyl-2,2':6',2''-terpyridine)­nickel(II) bis­(per­chlo­rate), [Ni(C21H15N3)2](ClO4)2 or [Ni(Ph-TPY)2](ClO4)2, bis­[4'-(4-meth­oxy­phen­yl)-2,2':6',2''-terpyridine]­manganese(II) bis­(per­chlo­rate), [Mn(C22H17N3O)2](ClO4)2 or [Mn(MeOPh-TPY)2](ClO4)2, and bis­(4'-phenyl-2,2':6',2''-ter­py­ridine)­manganese(II) bis­(per­chlo­rate), [Mn(C21H15N3)2](ClO4)2 or [Mn(Ph-TPY)2](ClO4)2. In all three cases, the com­plexes present distorted octa­hedral coordination polyhedra and the crystal packing is determined mainly by weak C—H⋯π inter­actions. All the com­pounds (except for the Ni derivatives, for which FT–IR, UV–Vis and thermal analysis are reported) were fully characterized by spectroscopic (FT–IR, UV–Vis and NMR spectroscopy) and thermal (TGA–DSC, thermogravimetric analysis–differential scanning calorimetry) methods.

The mol­ecular and crystal structure of a discrete [Ni8(μ4-OH)6(μ-4-Rpz)12]2− (R = H; pz = pyrazolate anion, C3H3N2−) cluster with an unprecedented, perfectly cubic arrangement of its eight Ni centers is reported, along with its lower-symmetry alkyl-functionalized (R = methyl and n-oct­yl) derivatives. Crystals of the latter two were obtained with two identical counter-ions (Bu4N+), whereas the crystal of the complex with the parent pyrazole ligand has one Me4N+ and one Bu4N+ counter-ion. The methyl derivative incorporates 1,2-di­chloro­ethane solvent mol­ecules in its crystal structure, whereas the other two are solvent-free. The compounds are tetra­butyl­aza­nium tetra­methyl­aza­nium hexa-μ4-hydroxido-dodeca-μ2-pyrazolato-hexa­hedro-octa­nickel, (C16H36N)(C4H12N)[Ni8(C3H3N2)12(OH)6] or (Bu4N)(Me4N)[Ni8(μ4-OH)6(μ-pz)12] (1), bis­(tetra­butyl­aza­nium) hexa-μ4-hydroxido-dodeca-μ2-(4-methyl­pyrazolato)-hexa­hedro-octa­nickel 1,2-di­chloro­ethane 7.196-solvate, (C16H36N)2[Ni8(C4H5N2)12(OH)6]·7.196C2H4Cl2 or (Bu4N)2[Ni8(μ4-OH)6(μ-4-Mepz)12]·7.196(ClCH2CH2Cl) (2), and bis­(tetra­butyl­aza­nium) hexa-μ4-hydroxido-dodeca-μ2-(4-octylpyrazolato)-hexa­hedro-octa­nickel, (C16H36N)2[Ni8(C11H19N2)12(OH)6] or (Bu4N)2[Ni8(μ4-OH)6(μ-4-nOctpz)12] (3). All counter-ions are disordered (with the exception of one Bu4N+ in 3). Some of the octyl chains of 3 (the crystal is twinned by non-merohedry) are also disordered. Various structural features are discussed and contrasted with those of other known [Ni8(μ4-OH)6(μ-4-Rpz)12]2− complexes, including extended three-dimensional metal–organic frameworks. In all three structures, the Ni8 units are lined up in columns.

Three organoplatinum(II) complexes bearing natural aryl­olefin and quinoline derivatives, namely, [4-meth­oxy-5-(2-meth­oxy-2-oxoeth­oxy)-2-(prop-2-en-1-yl)phen­yl](quinolin-8-olato)platinum(II), [Pt(C13H15O4)(C9H6NO)], (I), [4-meth­oxy-5-(2-oxo-2-propoxyeth­oxy)-2-(prop-2-en-1-yl)phen­yl](quinoline-2-carboxy­l­ato)platinum(II), [Pt(C15H19O4)(C10H6NO2)], (II), and chlorido­[4-meth­oxy-5-(2-oxo-2-propoxyeth­oxy)-2-(prop-2-en-1-yl)phen­yl](quinoline)­plat­inum(II), [Pt(C15H19O4)Cl(C9H7N)], (III), were synthesized and structurally characterized by IR and 1H NMR spectroscopy, and by single-crystal X-ray diffraction. The results showed that the cyclo­platinated aryl­olefin coordinates with PtII via the carbon atom of the phenyl ring and the C=Colefinic group. The deprotonated 8-hy­droxy­quinoline (C9H6NO) and quinoline-2-carb­oxy­lic acid (C10H6NO2) coordinate with the PtII atom via the N and O atoms in complexes (I) and (II) while the quinoline (C9H7N) coordinates via the N atom in (III). Moreover, the coordinating N atom in complexes (I)–(III) is in the cis position compared to the C=Colefinic group. The crystal packing is characterized by C—H⋯π, C—H⋯O [for (II) and (III)], C—H⋯Cl [for (III) and π–π [for (I)] inter­actions.

Three new 1H-indole derivatives, namely, 2-(bromo­meth­yl)-3-methyl-1-(phenyl­sulfon­yl)-1H-indole, C16H14BrNO2S, (I), 2-[(E)-2-(2-bromo-5-meth­oxy­phen­yl)ethen­yl]-3-methyl-1-(phenyl­sulfon­yl)-1H-indole, C24H20BrNO3S, (II), and 2-[(E)-2-(2-bromo­phen­yl)ethen­yl]-3-methyl-1-(phenyl­sulfon­yl)-1H-indole, C23H18BrNO2S, (III), exhibit nearly orthogonal orientations of their indole ring systems and sulfonyl-bound phenyl rings. Such conformations are favourable for inter­molecular bonding involving sets of slipped π–π inter­actions between the indole systems and mutual C—H⋯π hydrogen bonds, with the generation of two-dimensional monoperiodic patterns. The latter are found in all three structures, in the form of supra­molecular columns with every pair of successive mol­ecules related by inversion. The crystal packing of the compounds is additionally stabilized by weaker slipped π–π inter­actions between the outer phenyl rings (in II and III) and by weak C—H⋯O, C—H⋯Br and C—H⋯π hydrogen bonds. The structural significance of the different kinds of inter­actions agree with the results of a Hirshfeld surface analysis and the calculated inter­action energies. In particular, the largest inter­action energies (up to −60.8 kJ mol−1) are associated with pairing of anti­parallel indole systems, while the energetics of weak hydrogen bonds and phenyl π–π inter­actions are comparable and account for 13–34 kJ mol−1.

The crystal structures of 2-[1'-(carb­oxy­meth­yl)-4,4'-bi­pyridine-1,1'-diium-1-yl]acetate tetra­fluoro­borate, C14H13N2O4+·BF4− or (Hbcbpy)(BF4), and neutral 1,1'-bis­(carboxyl­atometh­yl)-4,4'-bi­pyridine-1,1'-diium (bcbpy), C14H20N2O8, are reported. The asymmetric unit of the (Hbcbpy)(BF4) consists of a Hbcbpy+ monocation, a BF4− anion, and one-half of a water mol­ecule. The BF4− anion is disordered. Two pyridinium rings of the Hbcbpy+ monocation are twisted at a torsion angle of 30.3 (2)° with respect to each other. The Hbcbpy monocation contains a carb­oxy­lic acid group and a deprotonated carboxyl­ate group. Both groups exhibit both a long and a short C—O bond. The cations are linked by inter­molecular hydrogen-bonding inter­actions between the carb­oxy­lic acid and the deprotonated carboxyl­ate group to give one-dimensional zigzag chains. The asymmetric unit of the neutral bcbpy consists of one-half of the bcbpy and two water mol­ecules. In contrast to the Hbcbpy+ monocation, the neutral bcbpy mol­ecule contains two pyridinium rings that are coplanar with each other and a carboxyl­ate group with similar C—O bond lengths. The mol­ecules are connected by inter­molecular hydrogen-bonding inter­actions between water mol­ecules and carboxyl­ate groups, forming a three-dimensional hydrogen-bonding network.

Two new [1-(phenyl­sulfon­yl)-1H-indol-2-yl]methanamine derivatives, namely, N-(3-meth­oxy­phen­yl)-N-{[1-(phenyl­sulfon­yl)-1H-indol-2-yl]meth­yl}acetamide, C24H22N2O4S, (I), and N-(2,5-di­meth­oxy­phen­yl)-N-{[1-(phenyl­sulfon­yl)-1H-indol-2-yl]meth­yl}benzene­sulfonamide, C29H26N2O6S2, (II), reveal a nearly orthogonal orientation of their indole ring systems and sulfonyl-bound phenyl rings. The sulfonyl moieties adopt the anti-periplanar conformation. For both compounds, the crystal packing is dominated by C—H⋯O bonding [C⋯O = 3.312 (4)–3.788 (8) Å], with the structure of II exhibiting a larger number, but weaker bonds of this type. Slipped π–π inter­actions of anti­parallel indole systems are specific for I, whereas the structure of II delivers two kinds of C—H⋯π inter­actions at both axial sides of the indole moiety. These findings agree with the results of Hirshfeld surface analysis. The primary contributions to the surface areas are associated with the contacts involving H atoms. Although II manifests a larger fraction of the O⋯H/H⋯O contacts (25.8 versus 22.4%), most of them are relatively distal and agree with the corresponding van der Waals separations.

Two new phenyl­sulfonyl­indole derivatives, namely, N-{[3-bromo-1-(phenyl­sulfon­yl)-1H-indol-2-yl]meth­yl}-N-(4-bromo-3-meth­oxy­phen­yl)benzene­sulfonamide, C28H22Br2N2O5S2, (I), and N,N-bis­{[3-bromo-1-(phenyl­sulfon­yl)-1H-indol-2-yl]meth­yl}benzene­sulfonamide, C36H27Br2N3O6S3, (II), reveal the impact of intra­molecular π–π inter­actions of the indole moieties as a factor not only governing the conformation of N,N-bis­(1H-indol-2-yl)meth­yl)amines, but also significantly influencing the crystal patterns. For I, the crystal packing is dominated by C—H⋯π and π–π bonding, with a particular significance of mutual indole–indole inter­actions. In the case of II, the mol­ecules adopt short intra­molecular π–π inter­actions between two nearly parallel indole ring systems [with the centroids of their pyrrole rings separated by 3.267 (2) Å] accompanied by a set of forced Br⋯O contacts. This provides suppression of similar inter­actions between the mol­ecules, while the importance of weak C—H⋯O hydrogen bonding to the packing naturally increases. Short contacts of the latter type [C⋯O = 3.389 (6) Å] assemble pairs of mol­ecules into centrosymmetric dimers with a cyclic R22(13) ring motif. These findings are consistent with the results of a Hirshfeld surface analysis and together they suggest a tool for modulating the supra­molecular behavior of phenyl­sulfonyl­ated indoles.

National Instrument 93-101 Derivatives: Business Conduct (the Rule) will come into force on September 28, 2024 (the Effective Date), pursuant to section 143.4 of the Securities Act (Ontario).

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This document is only available as a PDF.

The Minister of Finance has approved amendments to Ontario Securities Commission (OSC) Rule 91-507 Trade Repositories and Derivatives Data Reporting and consequential amendments to OSC Rule 13-502 Fees (collectively, the Amendments) pursuant to

1. Ontario Securities Commission Rule 91-507 Trade Repositories and Derivatives Data Reporting is amended by this Instrument.

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TORONTO – The Canadian Securities Administrators (CSA) today published

IntroductionThe members of the Canadian Securities Administrators (the CSA or we) are publishing for comment proposed amendments to National Instrument 94-101 Mandatory Central Counterparty Clearing of Derivatives (National Instrument 94

02-2014 : Montréal Exchange Derivatives Education Initiative Continues to Grow

01-2017 : MX Brings OptionsPlay to Canada's Derivatives Market

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