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1.  (2E)-1-(2-Methyl-4-phenyl­quinolin-3-yl)-3-(3-methyl­thio­phen-2-yl)prop-2-en-1-one 
In the title compound, C24H19NOS, the quinoline residue (r.m.s. deviation = 0.018 Å) is essentially orthogonal to both the phenyl [dihedral angle = 88.95 (8)°] and 2-thienyl [81.98 (9)°] rings. The carbonyl O atom lies to one side of the quinoline plane, the carbonyl C atom is almost coplanar and the remaining atoms of the chalcone residue lies to the other side, so that overall the mol­ecule has an L-shape. The conformation about the ethyl­ene bond [1.340 (2) Å] is E. In the crystal, a supra­molecular chain with the shape of a square rod aligned along the b-axis direction is sustained by C—H⋯π inter­actions, the π-systems being the heterocyclic rings.
doi:10.1107/S1600536813004753
PMCID: PMC3588408  PMID: 23476599
2.  (2E)-1-(2,4-Dimethyl­quinolin-3-yl)-3-phenyl­prop-2-en-1-one 
Two independent mol­ecules comprise the asymmetric unit of the title compound, C20H17NO, which differ in the orientation of the terminal phenyl ring with respect to the quinoline ring [the dihedral angles are 75.72 (11) and 84.53 (12)° for the two mol­ecules]. The conformation about each of the ethyl­ene bonds [1.329 (3) and 1.318 (3) Å] is E. The crystal structure features a combination of C—H⋯N, C—H⋯π and π–π contacts [inter-centroid between the phenyl ring and the quinoline benzene ring is 3.6024 (19) Å], generating a three-dimensional network.
doi:10.1107/S1600536813004765
PMCID: PMC3588443  PMID: 23476600
3.  Ethyl 2-amino-4-(4-bromo­phen­yl)-6-meth­oxy-4H-benzo[h]chromene-3-carboxyl­ate 
In the title compound, C23H20BrNO4, the pyran ring has a flattened boat conformation with the O and methine C atoms lying to one side of the plane [0.160 (5) and 0.256 (6) Å, respectively] defined by the remaining atoms. Nevertheless, the 4H-benzo[h]chromene ring system approximates a plane (r.m.s. deviation = 0.116 Å) with the bromo­benzene ring almost perpendicular [dihedral angle = 83.27 (16)°] and the ester group coplanar [C—C—C—O = 3.4 (5)°]; the meth­oxy substituent is also coplanar [C—O—C—C = 174.5 (3)°]. In addition to an intra­molecular N—H⋯O(ester carbon­yl) hydrogen bond, the ester carbonyl O atom also forms an inter­molecular N—H⋯O hydrogen bond with the second amine H atom, generating a zigzag supra­molecular chain along the c axis in the crystal packing. The chains are linked into layers in the bc plane by N—H⋯Br hydrogen bonds, and these layers are consolidated into a three-dimensional architecture by C—H⋯π inter­actions.
doi:10.1107/S160053681300490X
PMCID: PMC3588478  PMID: 23476606
4.  2-Methyl­sulfanyl-1,2,4-triazolo[1,5-a]quinazoline-5(4H)-thione 
In the title compound, C10H8N4S2, comprising fused six-, six- and five-membered rings, the mol­ecule is close to being planar (r.m.s. deviation of the non-H atoms = 0.041 Å). The S-bound methyl group is folded away from the single N atom of the triazole ring and the NH group of the six-membered ring, allowing for the formation of centrosymmetric eight-membered {⋯HNCN}2 synthons in the crystal. The resulting inversion dimers are connected into supra­molecular stacks aligned along the b-axis direction by π–π inter­actions [centroid–centroid distances = 3.6531 (12) and 3.7182 (12) Å].
doi:10.1107/S1600536813004881
PMCID: PMC3588520  PMID: 23476605
5.  4-Dimethyl­amino-1-(4-meth­oxy­phen­yl)-2,5-dioxo-2,5-dihydro-1H-pyrrole-3-carbonitrile 
In the title compound, C14H13N3O3, a twist occurs, as seen in the dihedral angle of 53.60 (12)° between the pyrrole and benzene rings. A three-dimensional architecture is formed in the crystal whereby layers of mol­ecules in the ac plane are connected by C—H⋯O and C—H⋯π inter­actions.
doi:10.1107/S1600536813004893
PMCID: PMC3588536  PMID: 23476607
6.  3-(4-Chloro­phen­yl)-5-(4-fluoro­phen­yl)-4,5-dihydro-1H-pyrazole-1-carbothio­amide 
In the title compound, C16H13ClFN3S, the pyrazole ring adopts an envelope conformation with the methine C atom being the flap atom. The chloro- and fluoro­benzene rings are twisted out of the plane of the pyrazole ring [dihedral angles = 15.12 (11) and 80.55 (10)°, respectively]. The amine group is orientated towards a ring N atom, forming an intra­molecular N—H⋯N hydrogen bond. This H atom also forms a hydrogen bond to the F atom, which along with N—H⋯S hydrogen bonding leads to a supra­molecular chain along the c axis. Connections between chains of the type Cl⋯π lead to a layer in the bc plane.
doi:10.1107/S1600536813004492
PMCID: PMC3588515  PMID: 23476591
7.  2-[5-(4-Fluoro­phen­yl)-3-(4-methyl­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia­zole 
In the title compound, C25H20FN3S, two independent mol­ecules comprise the asymmetric unit, which differ in the relative orientation of the fluoro­benzene ring with respect to the pyrazole ring to which it is attached [dihedral angles = 89.39 (17) and 75.23 (16)° in the two mol­ecules]. Each pyrazole ring adopts an envelope conformation with the methine C atom being the flap atom. There are additional twists in the mol­ecules, e.g. between the five-membered rings [dihedral angles = 18.23 (16) and 17.84 (16)°] and between the thia­zole and attached phenyl ring [10.26 (16) and 20.87 (15)°]. Overall, each mol­ecule has a T-shape. In the crystal, mol­ecules are connected into a three-dimensional architecture by weak C—H⋯π inter­actions.
doi:10.1107/S1600536813004339
PMCID: PMC3588500  PMID: 23476577
8.  5-(4-Fluoro­phen­yl)-3-(4-methyl­phen­yl)-4,5-dihydro-1H-pyrazole-1-carbothio­amide 
The central pyrazole ring in the title compound, C17H16FN3S, adopts an envelope conformation with the methine C atom bearing the 4-fluoro­phenyl substituent as the flap atom. Whereas the tolyl ring is slightly twisted out of the least-squares plane through the pyrazole ring [dihedral angle = 13.51 (11)°], the fluoro­benzene ring is almost perpendicular [dihedral angle = 80.21 (11)°]. The thio­amide group is almost coplanar with the N—N bond of the ring [N—N—C—N torsion angle = 1.2 (3)°] and the amine group forms an intra­molecular hydrogen bond with a ring N atom. In the crystal, supra­molecular double layers in the bc plane are formed via N—H⋯S, N—H⋯F and C—H⋯F inter­actions.
doi:10.1107/S1600536813004194
PMCID: PMC3588501  PMID: 23476571
9.  2-(2,4-Dichloro­phen­oxy­meth­yl)-5-(4-methyl­phen­yl)imidazo[2,1-b][1,3,4]thia­diazole1  
In the title compound, C18H13Cl2N3OS, the eight atoms comprising the central imidazo/thia­diazo­lethia­diazole residue are coplanar (r.m.s. deviation = 0.009 Å). The dihedral angle of 8.72 (13)° between the dichloro­benzene and tolyl rings reflects a twist about the O—C(benzene) bond; the Cm—O—Cb—Cb torsion angle = −168.5 (2)° (m = methyl­ene C and b is benzene C). Supra­molecular tapes along the b axis are found in the crystal structure which are mediated by π–π inter­actions occurring between centrosymmetrically related thia­diazole rings [inter-ring centroid distance = 3.6907 (16) Å] and between the benzene and tolyl rings [inter-ring centroid distance = 3.7597 (16) Å].
doi:10.1107/S160053681300384X
PMCID: PMC3588533  PMID: 23476564
10.  Tris(1,10-phenanthroline-κ2 N,N′)iron(II) bis­(1,1,3,3-tetra­cyano-2-eth­oxy­propenide) hemihydrate 
In the title hydrated mol­ecular salt, [Fe(C12H8N2)3](C9H5N4O)2·0.5H2O, the water mol­ecule site is half-occupied. The Fe—N bond lengths within the octa­hedral tris-chelate [Fe(phen)3]2+ ion (phen is 1,10-phenantroline) are indicative of a low-spin d 6 electronic configuration for the metal ion. The C—N, C—C and C—O bond lengths in the polynitrile anions indicate extensive electronic delocalization. In the crystal, the components are linked through O—H⋯N hydrogen bonds, forming [100] chains, as well as through Coulombic inter­actions.
doi:10.1107/S1600536812048611
PMCID: PMC3588335  PMID: 23476315
11.  Tetra­kis(triphenyl­phosphane-κP)silver(I) trifluoro­acetate ethanol monosolvate 
In the title solvated salt, [Ag(C18H15P)4](CF3CO2)·C2H5OH, the AgI atom is coordinated by four P atoms from triphenyl­phosphane ligands in a distorted tetra­hedral geometry. The anion and solvent are engaged in weak O—H⋯O hydrogen bonds. Of the four triphenyl­phosphane ligands, two each have an equally disordered phenyl ring while the AgI atom is disordered over two positions in a 0.9595 (15):0.0405 (15) ratio and the trifluoro­acetate anion is equally disordered over two positions with respect to the lattice ethanol mol­ecule.
doi:10.1107/S1600536812045060
PMCID: PMC3588779  PMID: 23468744
12.  Tetra­kis(triphenyl­arsane-κAs)silver(I) trifluoro­acetate hemihydrate methanol hemisolvate 
The AgI atom in the title hydrated solvated salt, [Ag(C18H15As)4](CF3CO2)·0.5CH3OH·0.5H2O, is coordinated by four As atoms from triphenyl­arsane ligands in a distorted tetra­hedral geometry. In the crystal, O—H⋯O hydrogen bonding occurs between carboxyl­ate groups of anions and lattice solvent mol­ecules. Of the four triphenyl­arsane ligands in the Ag complex cation, two each have an equally disordered phenyl ring while the trifluoro­acetate anion is disordered over two positions with respect to the lattice methanol and water mol­ecules which both show half-occupyncy. The crystal studied was a non-merohedral twin with a 13.6 (1)% contribution of the minor twin component.
doi:10.1107/S1600536812045072
PMCID: PMC3588780  PMID: 23468745
13.  Bis{μ-2-[(pyrimidin-2-yl)amino­meth­yl]phenolato}-κ2 N 1:O;κ2 O:N 1-bis­({2-[(pyrimidin-2-yl-κN)amino­meth­yl]phenol}silver(I)) dihydrate 
The AgI atom in the title centrosymmetric dinuclear compound, [Ag2(C11H10N3O)2(C11H11N3O)2]·2H2O, shows a T-shaped coordination arising from bonding to the N atom of a neutral 2-[(pyrimidin-2-yl)amino­meth­yl]phenol ligand, the N atom of the 2-[(pyrimidin-2-yl)amino­meth­yl]phenolate anion [N—Ag—N = 171.8 (1)°] and the terminal O atom of the other anion [Ag—O = 2.606 (3) Å]. A pair of 2-[(pyrimidin-2-yl)amino­meth­yl]phenolate anions link the two AgI atoms to form the dinuclear compound. In the crystal, adjacent dinuclear mol­ecules are linked to the lattice water mol­ecules, generating an O—H⋯O- and N—H⋯O-connected three-dimensional network. In the crystal, the hy­droxy H atom is disordered over two positions in a 1:1 ratio; one half-occupancy H atom is connected to one hy­droxy group, whereas the other half-occupancy H atom is connected to another hy­droxy group.
doi:10.1107/S1600536812045783
PMCID: PMC3588781  PMID: 23468746
14.  Poly[[[μ3-(E)-N-(pyridin-4-yl­methyl­idene)hy­droxy­laminato-κ3 O:N:N′][μ2-(E)-N-(pyridin-4-yl­methyl­idene)hydroxyl­amine-κ2 N:N′][(E)-N-(pyridin-4-yl­methyl­idene-κN)hydroxyl­amine]­disilver(I)] nitrate] 
The title coordination polymer, {[Ag2(C6H5N2O)(C6H6N2O)2]NO3}n, features a deprotonated N-(pyridin-4-yl­methyl­idene)hy­droxy­laminate anion and two neutral N-(pyridin-4-yl­methyl­idene)hydroxyl­amine mol­ecules in the asymmetric unit. The anion connects three AgI atoms through its O and two N-donor atoms. One neutral ligand functions in a monodentate mode; the other functions in a bridging mode, binding though its two N atoms. The coordination geometry of the two independent metal atoms is T-shaped; the manner of bridging gives rise to a layer motif parallel to (100). In the crystal, the nitrate ion is disordered over two positions in a 1:1 ratio, and is sandwiched between adjacent layers. O—H⋯O hydrogen bonding is present between nitrate ions and layers, and also between adjacent layers.
doi:10.1107/S1600536812046090
PMCID: PMC3588782  PMID: 23468747
15.  (Nitrato-κ2 O,O′)bis­[(E)-N-(pyridin-4-yl­methyl­idene-κN)hy­droxy­amine]­silver(I) 
In the mononuclear title compound, [Ag(NO3)(C6H6N2O)2], the AgI atom is located on a twofold rotation axis and the nitrate-chelated AgI atom is further coordinated by two aromatic N atoms of hydroxyl­amine ligands in a distorted tetra­hedral geometry. In the crystal, the nitrate ion has 2 symmetry with the N atom and one O atom located on the twofold rotation axis, and is linked to hy­droxy groups of the hydroxyl­amine ligands by O—H⋯O hydrogen bonds, generating a chain running along the b axis.
doi:10.1107/S1600536812046107
PMCID: PMC3588783  PMID: 23468748
16.  Tris{2-[(pyrimidin-2-yl-κN)amino­meth­yl]phenol}silver(I) nitrate 
The AgI atom in the title compound, [Ag(C11H11N3O)3]NO3, shows a T-shaped coordination arising from bonding to the N atom of three N-heterocycles; the geometry is distorted towards square pyramidal owing to two weak Ag⋯Onitrate inter­actions [Ag⋯O = 2.691 (5) and 3.073 (5) Å]. The cation and anion are linked by O—H⋯N and N—H⋯O hydrogen bonds, generating a three-dimensional network.
doi:10.1107/S1600536812046119
PMCID: PMC3588784  PMID: 23468749
17.  Dimeth­yl(1,10-phenanthroline-κ2 N,N′)bis­(thio­cyanato-κN)tin(IV) 
The SnIV atom in the title compound, [Sn(CH3)2(NCS)2(C12H8N2)], is located on a twofold rotation axis in a distorted octa­hedral enviroment. The methyl groups are trans to each other [C—Sn—C = 175.7 (3)°], whereas the thio­cyanate groups are cis to each other.
doi:10.1107/S1600536812047691
PMCID: PMC3588785  PMID: 23468750
18.  Di-μ2-ethano­lato-octa­methyl­bis­(μ-4-methyl-5-sulfanyl­idene-4,5-dihydro-1H-1,2,4-triazol-1-ido-κ2 N 1:N 2)di-μ3-oxido-tetra­tin(IV) 
The tetra­nuclear title compound, [Sn4(CH3)8(C2H5O)2O2(C3H4N3S)2], lies about a center of inversion; the mol­ecule features a three-rung-staircase Sn4O4 core in which two SnIV atoms are bridged by the 4-methyl-5-sulfanyl­idene-4,5-dihydro-1H-1,2,4-triazol-1-ide group. The negatively charged N atom of the group binds to the terminal SnIV atom at a shorter distance [Sn—N = 2.240 (3) Å] compared with the neutral N atom that binds to the central SnIV atom [Sn← N = 2.641 (3) Å]. The terminal SnIV atom is five-coordinate in a cis-C2SnNO2 trigonal–bipyramidal geometry [C—Sn—C = 127.5 (2)°], whereas the central SnIV atom is six-coordinate in a C2SnNO3 skew-trazepoidal bipyramidal geometry [C—Sn—C = 145.0 (2)°].
doi:10.1107/S1600536812047708
PMCID: PMC3588786  PMID: 23468751
19.  Di-μ2-isopropano­lato-octa­methyl­bis­(μ-4-methyl-5-sulfanyl­idene-4,5-dihydro-1H-1,2,4-triazol-1-ido-κ2 N 1:N 2)di-μ3-oxido-tetra­tin(IV) 
The tetra­nuclear title compound, [Sn4(CH3)8(C3H7O)2O2(C3H4N3S)2], lies about a center of inversion; the mol­ecule features a three-rung-staircase Sn4O4 core in which two SnIV atoms are bridged by the 4-methyl-5-sulfanyl­idene-4,5-dihydro-1H-1,2,4-triazol-1-ide group. The negatively charged N atom of the group binds to the terminal SnIV atom at a shorter distance [Sn—N = 2.236 (2) Å] compared with the neutral N atom that binds to the central SnIV atom [Sn← N = 2.805 (2) Å]. The terminal SnIV atom is five-coordinate in a cis-C2SnNO2 trigonal–bipyramidal geometry [C—Sn—C = 136.4 (1)°], whereas the central SnIV atom is six-coordinate in a C2SnNO3 skew-trazepoidal bipyramidal geometry [C—Sn—C = 145.4 (1)°]. The C atoms of the isopropoxy group are disordered over two positions in a 0.591 (7):0.409 (7) ratio.
doi:10.1107/S160053681204771X
PMCID: PMC3588787  PMID: 23468752
20.  Bis[μ-(E)-N-(pyridin-3-yl­methyl­idene)hy­droxy­amine]-κ2 N 1:N 3;κ2 N 3:N 1-bis­{[(E)-N-(pyridin-3-yl­methyl­idene-κN)hy­droxy­amine]­silver(I)} dinitrate 
In the centrosymmetric dinuclear title AgI compound, [Ag2(C6H6N2O)4](NO3)2, the aromatic amine-coordinated AgI atom is further bridged by two hydroxyl­amine mol­ecules that use aromatic and oxime N atoms for bridging, and it exists in a distorted trigonal-planar geometry. In the crystal, the nitrate anions link to the dinuclear compound mol­ecules via O—H⋯O hydrogen bonds, generating a chain running along the a-axis direction.
doi:10.1107/S1600536812045898
PMCID: PMC3588788  PMID: 23468753
21.  Di-μ3-acetato-bis­{μ-6,6′-dieth­oxy-2,2′-[propane-1,2-diylbis(nitrilo­methanylyl­idene)]diphenolato}dicadmiumdisodium ethanol 0.67-solvate 
In the crystal of the title compound, [Cd2Na2(C2H3O2)2(C21H24N2O4)2]·0.67C2H6O, the doubly deprotonated Schiff base ligand N,N′,O,O′-chelates to the CdII cation, which is also O,O′-chelated by the acetate ion. Two Cd–Schiff base units are connected to two Na+ atoms to form the tetra­nuclear complex, in which the Cd2+ and Na+ cations show distorted octa­hedral coordinations. The asymmetric unit consists of half a tetra­nuclear mol­ecule (lying on an inversion center) and a full tetra­nuclear mol­ecule (lying on a general position) along with a lattice ethanol mol­ecule, which links to the coordinating acetate ion via an O—H⋯O hydrogen bond. In the crystal, the propyl and ethyl groups of the complex mol­ecule are disordered over two positions in a 1:1 ratio; the ethyl group of the lattice ethanol mol­ecule is also equally disordered over two positions.
doi:10.1107/S1600536812047356
PMCID: PMC3588789  PMID: 23468754
22.  [μ-1,2,3,4-Tetra­kis(pyridin-4-yl)butane-κ2 N 1:N 4]bis­[trimeth­yl(thio­cyanato-κN)tin(IV)] 
In the title compound, [Sn2(CH3)6(NCS)2(C24H22N4)], the 1,2,3,4-tetra­kis­(pyridin-4-yl)butane ligand uses the pyridine N atoms at the ends of the butyl chain to coordinate to two trimethylthiocyanatotin(IV) units, forming a dinuclear structure. The SnIV atom in the mol­ecule shows a distorted trans-trigonal–bipyramidal coordination with the methyl groups in equatorial positions. The mol­ecule lies on a center of inversion, with the mid-point of the butyl chain coinciding with this symmetry element. In the crystal, weak C—H⋯π inter­actions occur between pyridine rings of adjacent mol­ecules.
doi:10.1107/S160053681204737X
PMCID: PMC3588790  PMID: 23468755
23.  Dimethyl­bis­(2-methyl­quinolin-8-olato-κ2 N,O)tin(IV) 
The SnIV cation in the title compound, [Sn(CH3)2(C10H8NO)2], is N,O-chelated by two 2-methyl­quinolin-8-olate anions and coordinated by two methyl groups in a skew-trapezoidal bipyramidal geometry. In the mol­ecule, the two quinoline ring systems are twisted to one another at 10.91 (18)°. The dimethyl­tin skeleton [C—Sn—C = 149.6 (2)°] is bent over the longer edge of the trapezoid that is defined by the four chelating atoms. Weak inter­molecular C—H⋯O hydrogen bonding occurs in the crystal.
doi:10.1107/S1600536812047393
PMCID: PMC3588791  PMID: 23468756
24.  1-Benzoyl-3-(4-chloro­phen­yl)thio­urea dichloro­methane hemisolvate 
In the title hemisolvate, C14H11ClN2OS·0.5CH2Cl2, an anti disposition is found for the thione and ketone atoms, as well as the N—H H atoms; the dichloro­methane C atom lies on a twofold axis. The central chromophore (including the two adjacent ipso C atoms) is planar (r.m.s. deviation = 0.021 Å) owing to the presence of an intra­molecular N—H⋯O hydrogen bond, which closes an S(6) loop. Significant twists are evident in the mol­ecule, the dihedral angles between the central moiety and the phenyl and benzene rings being 29.52 (7) and 40.02 (7)°, respectively. In the crystal, eight-membered {⋯HNC= S}2 synthons with twofold symmetry form via N—H⋯S hydrogen bonds. The dimers are connected into a supra­molecular chain along [111] by C—H⋯O inter­actions. The chains stack along the c axis, forming columns which define channels in which the occluded dichloro­methane mol­ecules reside.
doi:10.1107/S1600536812045588
PMCID: PMC3588922  PMID: 23476158
25.  3-Benzoyl-1-(2-meth­oxy­phen­yl)thio­urea 
In the title compound, C15H14N2O2S, the central C2N2OS moiety is planar (r.m.s. deviation of fitted atoms = 0.0336 Å). This is ascribed to the formation of an S(6) loop stabilized by an intra­molecular N—H⋯O hydrogen bond; additional intramolecular N—H⋯O and C—H⋯S contacts are also noted. The dihedral angles between the central unit and the phenyl and benzene rings are 23.79 (7) and 29.52 (5)°, respectively. The thione S and ketone O atoms are mutually anti, as are the N—H H atoms; the O atoms lie to the same side of the mol­ecule. Centrosymmetric eight-membered {⋯HNC=S}2 synthons feature in the crystal packing. The resulting inversion dimers stack along the a axis and are connected into a three-dimensional structure by C—H⋯O and C—H⋯π inter­actions.
doi:10.1107/S160053681204456X
PMCID: PMC3588812  PMID: 23468777

Results 1-25 (1188)