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1.  Crystal structures of 2-meth­oxy­isoindoline-1,3-dione, 1,3-dioxoisoindolin-2-yl methyl carbonate and 1,3-dioxo-2,3-di­hydro-1H-benzo[de]isoquinolin-2-yl methyl carbonate: three anti­convulsant compounds 
In three potentially anti­convulsant compounds, of which two are isoindoline derivatives and one an iso­quinoline derivative, the central moiety is planar. In the crystals of all three compounds, there are C—H⋯O hydrogen bonds present linking the mol­ecules into two-dimensional slabs for the isoindoline derivatives, and into a three-dimensional framework for the iso­quinoline derivative.
The title compounds, C9H7NO3, (1), C10H7NO5, (2), and C14H9NO5, (3), are three potentially anti­convulsant compounds. Compounds (1) and (2) are isoindoline derivatives and (3) is an iso­quinoline derivative. Compounds (2) and (3) crystallize with two independent mol­ecules (A and B) in their asymmetric units. In all three cases, the isoindoline and benzoiso­quinoline moieties are planar [r.m.s. deviations are 0.021 Å for (1), 0.04 and 0.018 Å for (2), and 0.033 and 0.041 Å for (3)]. The substituents attached to the N atom are almost perpendicular to the mean planes of the heterocycles, with dihedral angles of 89.7 (3)° for the N—O—Cmeth­yl group in (1), 71.01 (4) and 80.00 (4)° for the N—O—C(=O)O—Cmeth­yl groups in (2), and 75.62 (14) and 74.13 (4)° for the same groups in (3). In the crystal of (1), there are unusual inter­molecular C=O⋯C contacts of 2.794 (1) and 2.873 (1) Å present in mol­ecules A and B, respectively. There are also C—H⋯O hydrogen bonds and π–π inter­actions [inter-centroid distance = 3.407 (3) Å] present, forming slabs lying parallel to (001). In the crystal of (2), the A and B mol­ecules are linked by C—H⋯O hydrogen bonds, forming slabs parallel to (10-1), which are in turn linked via a number of π–π inter­actions [the most significant centroid–centroid distances are 3.4202 (7) and 3.5445 (7) Å], forming a three-dimensional structure. In the crystal of (3), the A and B mol­ecules are linked via C—H⋯O hydrogen bonds, forming a three-dimensional structure, which is consolidated by π–π inter­actions [the most significant inter-centroid distances are 3.575 (3) and 3.578 (3) Å].
PMCID: PMC4257384  PMID: 25552964
crystal structure; anti­convulsant; isoindoline; iso­quinoline; indoline
2.  Crystal structure of (5R)-5-[(1S)-1,2-di­hydroxy­eth­yl]-4-meth­oxy-3-phenyl-2,5-di­hydro­furan-2-one 
In the title compound, C13H14O5, the furan ring is essentially planar [maximum deviation = 0.031 (3) Å] with a stereogenic center (R) at the sp 3 hybridized C atom. The C atom bearing the dihy­droxy ethyl group is S. The absolute configuration is based on the precursor in the synthesis. The two O—H groups are in an anti conformation with respect to each other. The mean plane of the furan­one group is twisted by 8.2 (4)° from that of the phenyl ring. In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds involving furan­one C=O groups and symmetry-related hy­droxy groups, forming a two-dimensional network parallel to (001). Weak C—H⋯O hydrogen bonds are observed within the two-dimensional network.
PMCID: PMC4257168  PMID: 25484718
Crystal structure; l-ascorbic acid derivative; hydrogen bonding.; crystal structure
3.  Crystal structure of anhydrous poly[bis­(μ2-sarcosinato-κ3 O,N:O′)copper(II)] 
The copper(II) ion of the anhydrous form of bis­(sarcosinato)copper(II) exhibits a [4 + 2] coordination sphere with four shorter equatorial bonds to the N and carboxyl­ate O atoms of two sarcosinate anions, and two longer axial bonds to O atoms of neighboring complexes, leading to a sheet structure parallel to (001).
The title compound, [Cu(C3H6NO2)2]n, is a bis-complex of the anion of sarcosine (N-methyl­glycine). The asymmetric unit consists of a copper(II) ion, located on a center of inversion, and one mol­ecule of the uninegative sarcosinate anion. The copper(II) ion exhibits a typical Jahn–Teller distorted [4 + 2] coordination geometry. The four shorter equatorial bonds are to the nitro­gen and carboxyl­ate O atoms of two sarcosinate anions, and the longer axial bonds are to carboxyl­ate O atoms of neighboring complexes. The overall structure is made up from two chains formed by these longer axial Cu—O bonds, one extending parallel to [011] and the other parallel to [0-11]. Each one-dimensional array is connected by the equatorial bridging moieties to the chains on either side, creating an extended two-dimensional framework parallel to (100). There is a single inter­molecular hydrogen-bonding inter­action within the sheets between the amino NH group and an O atom of an adjacent mol­ecule.
PMCID: PMC4257172  PMID: 25484653
crystal structure; anhydrous bis­(sarcosinato)copper(II); non-proteinogenic amino acid
4.  Crystal structure of (N 1-benzyl-N 1,N 2,N 2-tri­methyl­ethane-1,2-di­amine-κ2 N,N′)di­chloridomercury(II) 
The mol­ecular structure of [HgCl2(C12H20N2)] is a rare example where the HgII atom is bound to a Cl2N2 donor set for which the N atoms originate from aliphatic tertiary amine groups.
In the structure of the title compound, [HgCl2(C12H20N2)], the HgII atom has a distorted tetra­hedral coordination sphere defined by two tertiary amine N-atom donors, as well as two Cl− anions [the dihedral angle between the N—Hg—N and Cl—Hg—Cl planes is 82.80 (9)°]. The five-membered chelate ring adopts an envelope conformation, with puckering parameters of Q(2) = 0.446 (6) Å and ϕ(2) = 88.8 (6)°, with the two amine CH3 substituents on opposite sides of the ring. In the crystal, the mol­ecules are linked by C—H⋯Cl inter­actions into a zigzag chain parallel to [101].
PMCID: PMC4186188  PMID: 25309156
crystal structure; mercury complex; tertiary amine donors
5.  Crystal structure of N 1-benzyl-N 1,N 2,N 2-tri­methyl­ethane-1,2-diaminium dichloride 
In the title mol­ecular salt, C12H22N2 2+·2Cl−, which was obtained as a by-product in the attempted synthesis of a mercury derivative, the conformation of the N—C—C—N bond in the cation is anti [torsion angle = 175.1 (10)°]. In the crystal, the cations are linked to the anions by N—H⋯Cl hydrogen bonds, generating ion-triplets. These are linked by numerous weak C—H⋯Cl inter­actions, generating a three-dimensional network. The structure was refined as an inversion twin.
PMCID: PMC4186135  PMID: 25309248
crystal structure; hydrogen bonds; C—H⋯Cl inter­actions; ion-triplets; inversion twin
6.  Crystal structure of 4-bromo-N-(2-bromo-3-nitro­benz­yl)-2-nitro­naphthalen-1-amine 
In the title compound, C17H11Br2N3O4, the dihedral angle between the planes of the naphthalene system and the benzene ring is 52.86 (8)°. The nitro substituent and the attached naphthalene system are almost coplanar [dihedral angle = 5.6 (4)°], probably as a consequence of an intra­molecular N—H⋯O hydrogen bond with the amine group. The nitro substituent attached to the benzene ring is disordered over two sets of sites with occupancies of 0.694 (3) and 0.306 (3). The major component deviates significantly from the ring plane [dihedral angle = 53.6 (2)°]. In the crystal, the mol­ecules are linked into a three-dimensional array by extensive π–π inter­actions involving both the naphthalene and benzene rings [range of centroid–centroid distances = 3.5295 (16)–3.9629 (18) Å] and C—H⋯O inter­actions involving the methyl­ene H atoms and the phenyl-attached nitro group.
PMCID: PMC4186169  PMID: 25309280
crystal structure; naphthalen-1-amine; π–π inter­actions; hydrogen bonding; aryl­selenium compounds; photoluminescent seleno­spiro­cyclic compounds
7.  2-Bromo-5-tert-butyl-N-methyl-N-[2-(methyl­amino)­phen­yl]-3-(1-methyl-1H-benzimidazol-2-yl)benzamide 
In the title compound, C27H29BrN4O, benzimidazole ring system and the amide moiety are planar [r.m.s. deviations = 0.016 (2) and 0.017 (1) Å, respectively]. The mol­ecule adopts a conformation in which the amide linkage is almost perpendicular to the central ring [dihedral angle = 85.79 (8)°], while the benzimidazole ring system makes a dihedral angle of 70.26 (11)° with the central ring. In the crystal, the mol­ecules form dimers through N—H⋯O hydrogen bonds and C—H⋯O interactions. These dimers are further linked into zigzag ribbons along [201] by weak C—H⋯Br inter­actions. As a result of the bulky nature of the mol­ecule, as evidenced by the large dihedral angles between rings, there is little evidence for any π–π inter­actions.
PMCID: PMC4120529  PMID: 25161598
crystal structure
8.  4-(Furan-2-carbon­yl)piperazin-1-ium 3,5-di­nitro­benzoate 
In the cation of the title salt, C9H13N2O2 +·C7H3N2O6 −, the piperazine ring adopts a slightly distorted chair conformation. Twofold rotational disorder is exhibited by the furan ring in a 0.430 (4):0.570 (4) ratio. In the crystal, N—H⋯O hydrogen bonds link the ions into chains along [010]. Additional weak C—H⋯O inter­actions are observed, leading to a supra­molecular layer parallel to (011).
PMCID: PMC4051063  PMID: 24940274
9.  (E)-2-{[4-(Di­methyl­amino)­benzyl­idene]amino}-5-nitro­phenol 
The title Schiff base compound, C15H15N3O3, crystallizes with two mol­ecules (A and B) in the asymmetric unit. Each mol­ecule adopts an E conformation around the C= N imine bond. The two mol­ecules have minor differences in their conformations. In mol­ecule A, the dihedral angle between the nitro group and its benzene ring is 2.1 (2)° and that between the two benzene rings is 0.88 (7)°, while the corresponding angles for mol­ecule B are 5.7 (1) and 2.45 (6)°, respectively. In each mol­ecule, there is an intra­molecular O—H⋯N hydrogen bond. In the crystal, inversion-related mol­ecules are linked via O—H⋯O hydrogen bonds forming A–A and B–B dimers. These dimers are linked via C—H⋯O hydrogen bonds involving the nitro O atoms, forming A–A–A and B–B–B slabs that lie parallel to one another and to (010).
PMCID: PMC4011306  PMID: 24860394
10.  2-Chloro-N-(2-chloro­benzo­yl)-N-(2-ethyl-4-oxo-3,4-di­hydro­quinazolin-3-yl)benzamide 
In the title compound, C24H17Cl2N3O3, the quinazolinone ring system is close to planar (r.m.s. deviation = 0.0132 Å), with the imide unit almost perpendicular to it, subtending a dihedral angle of 89.1 (1)°. However, the imide unit itself is not planar, the dihedral angle between the two O=C—N components being 34.6 (1)°. The dihedral angle between the two chlorobenzene rings is 40.50 (7)°, while the angles between these rings and the imide moiety are 54.6 (1) and 58.2 (1)°, respectively. The dihedral angles between the 2-chloro­phenyl rings and the quinazolinone ring system are 48.77 (5) and 32.92 (7)° for rings A and B, respectively. In the crystal, weak C—H⋯O inter­actions link the mol­ecules into a three-dimensional array.
PMCID: PMC3998615  PMID: 24826190
11.  (E)-2-{[(Furan-2-ylmeth­yl)imino]­meth­yl}-4-nitro­phenol 
In the title compound, C12H10N2O4, the furan-2-ylmethyl group is disordered over two sets of sites, with refined occupancies of 0.858 (3) and 0.143 (3). In the major component of disorder, the dihedral angle between the furan and benzene rings is 63.1 (2)° and for the minor component this value is 67.9 (6)°. The planes of the nitro group and the attached benzene ring form a dihedral angle of 4.34 (17)°. In the crystal, inversion-related mol­ecules are linked by two pairs of weak C—H⋯O inter­actions, one involving the nitro group and the other involving the O—H group as an acceptor. As a result of these associations, ribbons are formed along [120]. A strong intra­molecular O—H⋯N hydrogen bond is observed.
PMCID: PMC3998629  PMID: 24826153
12.  Tri­phenyl­tellurium chloride 
The asymmetric unit of the title compound, C18H15ClTe, contains two mol­ecules which are in inverted orientations. The compound displays a tetra­hedral geometry around the Te atom in spite of there being five electron domains. This is attributed to the fact that the lone pair is not sterically active. The dihedral angles between the three phenyl rings are 76.51 (16)/73.75 (16)/71.06 (17) and 78.60 (17)/77.67 (16)/79.11 (16)° in the two mol­ecules. The crystal packing features eight C—H⋯π inter­actions.
PMCID: PMC3998628  PMID: 24826133
13.  4-Hy­droxy-5-meth­oxy-N,1-dimethyl-2-oxo-N-[4-(tri­fluoro­meth­yl)phen­yl]-1,2-di­hydro­quinoline-3-carboxamide 
The title compound, C20H17F3N2O4, named tasquinimod, is a second-generation oral quinoline-3-carboxamide analogue, which is currently in phase III clinical trials for the treatment of metastatic prostate cancer. The quinoline unit is almost planar (r.m.s. deviation of fitted atoms = 0.0075 Å). The carboxamide side chain, substituted at position 3, is tilted by 88.07 (7)° to the quinoline plane. Both the methyl and carbonyl groups of this carboxamide side chain are in a syn conformation. The 4-(tri­fluoro­meth­yl)phenyl plane is inclined at 50.62 (17)° to the plane of the carboxamide side chain, and at 87.14 (4)° to the plane of the quinoline ring system. The 4-hy­droxy H atom acts as a double proton donor in an intra­molecular hydrogen bond to the 5-position meth­oxy O atom and in an inter­molecular contact to the 2-oxo group, generating a chain along [010] in the crystal structure.
PMCID: PMC3998412  PMID: 24765003
14.  Bis[(2-methyl­benz­yl)bis­(pyridin-2-ylmethyl-κN)amine-κN]manganese(II) bis­(perchlorate) 
In the title complex, [Mn(C20H21N3)2](ClO4)2, two tridentate (2-methyl­benz­yl)bis­(pyridin-2-ylmeth­yl)amine (L) ligands form the MnII complex [MnL 2](ClO4)2. The MnII ion lies on a twofold axis and the complex cation is significantly distorted from regular octa­hedral geometry. The packing is stabilized by weak C—H⋯O inter­actions between the cations and anions, which link them into a zigzag ribbon along [101]. The perchlorate anion is disordered and was constrained to be tetra­hedral with two orientations having occupancies of 0.768 (4) and 0.232 (4). The 2-methylbenzyl moiety is also disordered over two sets of sites, with occupancies of 0.508 (15) and 0.492 (15).
PMCID: PMC3998448  PMID: 24764935
15.  Bis(η5-penta­methyl­cyclo­penta­dien­yl)aluminium tetra­bromido­aluminate 
The title compound, [Al(C10H15)2][AlBr4], was formed during the reduction of a mixture of Cp*AlBr2 and AlBr3. The AlIII atoms of the two crystallographically independent cations each lie on an inversion center, and the [AlBr4]− anions are on general positions. At 123 K, the structure exhibits disorder in two of the Br atoms of the [AlBr4]− ion, with a ratio occupancy of 0.733 (6): 0.267 (3). In the crystal, there is possible weak hydrogen bonding between some methyl groups and Br atoms. The interactions link the moieties in a three-dimensional array.
PMCID: PMC3998496  PMID: 24764951
16.  Tris(2,6-dibenzoyl-4-methyl­phenolato-κ2 O 1,O 2)cobalt(III) 
In the title compound, [Co(C21H15O3)3], the CoIII ion is coordinated in a slightly distorted octa­hedral environment by three phenolate O and three benzoyl O atoms from three monoanionic bidentate 2,6-dibenzoyl-4-methyl­phenolate ligands. The dihedral angles between the mean planes of the central phenolate rings and the peripheral phenyl rings are 46.62 (10)/87.06 (9), 60.44 (8)/23.13 (8) and 46.49 (6)/65.29 (6)°. The crystal packing is stabilized by weak inter­molecular C—H⋯O inter­actions. Mol­ecules are further linked by two π–π [centroid–centroid distances = 3.8612 (14) and 3.9479 (14) Å] and four C—H⋯π inter­actions, forming a three-dimensional network.
PMCID: PMC3998268  PMID: 24764829
17.  1-Aza­niumyl­cyclo­butane-1-carboxyl­ate monohydrate 
In the title compound, C5H9NO2·H2O, the amino acid is in the usual zwitterionic form involving the α-carboxyl­ate group. The cyclo­butane backbone of the amino acid is disordered over two conformations, with occupancies of 0.882 (7) and 0.118 (7). In the crystal, N—H⋯O and O—H⋯O hydrogen bonds link the zwitterions [with the water molecule involved as both acceptor (with the NH3 +) and donor (through a single carboxylate O from two different aminocyclobutane carb­oxylate moities)], resulting in a two-dimensional layered structure lying parallel to (100).
PMCID: PMC3998359  PMID: 24764920
18.  Poly[tetrakis(μ-1,1,1,3,3,3-hexafluoropropan-2-olato)iron(II)dipotassium] 
The title compound, [K2Fe{OCH(CF3)2}4]n, was formed from the reaction of potassium hexa­fluoro­isopropoxide with iron(II) chloride in toluene. The FeII atom has a highly distorted tetra­hedral coordination environment. All four of the non-equivalent hexa­fluoro­isoprop­oxy O atoms link the FeII atoms to one of the K+ atoms in an alternating chain of Fe—O—K—O fused four-membered rings, with K—Fe distances of 3.715 (2) and 3.717 (2) Å. This K+ atom is also bridged to eight of the F atoms. The other K+ atom is bonded to only two of the O atoms, but has seven short K⋯F contacts, one of which links the chains into a three-dimensional arrangement. Weak hydrogen bonding between the lone H atoms on the hexa­fluoro­isoprop­oxy groups and F atoms is also present. The crystal studied was refined as an inversion twin.
PMCID: PMC3998246  PMID: 24764807
19.  N-(3-Chloro-1,4-dioxo-1,4-di­hydro­naph­thalen-2-yl)-N-propionylpropionamide 
In the title mol­ecule, C16H14ClNO4, the four essentially planar atoms of the imide group [r.m.s. deviation = 0.0286 (11) Å] form a dihedral angle of 77.36 (13)° with the naphtho­quinone group [maximun deviation = 0.111 (2) Å for the carbonyl O atom in the naphthalene 1-position] and the two imide carbonyl groups are oriented anti with respect to each other. In the crystal, mol­ecules are connected by weak C—H⋯O hydrogen bonds, as well as π–π stacking inter­actions [centroid–centroid distance = 3.888 (3) Å], forming a three-dimensional network.
PMCID: PMC3998274  PMID: 24764835
20.  Di­aqua­bis­(2-ethyl-5-methyl­imidazole-4-sulfonato-κ2 N 3,O)nickel(II) dihydrate 
In the title complex, [Ni(C6H9N2O3S)2(H2O)2]·2H2O, the NiII atom lies on an inversion center and is chelated by N and O atoms of two symmetry-equivalent imidazole­sulfonate ligands in the basal plane, and two water O atoms in axial positions in an overall octa­hedral configuration. The crystal structure displays O—H⋯O and N—H⋯O hydrogen bonds, which connect the components into an extended three-dimensional network.
PMCID: PMC3914054  PMID: 24526946
21.  Ethyl 6-(4-chloro­phen­yl)-4-(4-fluoro­phen­yl)-2-oxo­cyclo­hex-3-ene-1-carboxyl­ate 
The asymmetric unit of the title compound, C21H18ClFO3, contains two independent mol­ecules. In one mol­ecule (A), the 4-chloro­phenyl, oxo­cyclo­hex-3-ene, carboxyl­ate, and ethyl groups were refined as disordered over two sets of sites with a 0.684 (5):0.316 (5) ratio. The cyclo­hexene ring in the disordered mol­ecule is in a slightly distorted envelope conformation for the major component (with the C atom bound to the carboxylate group being the flap atom) and in a screw-boat conformation for the minor component. In the ordered mol­ecule (B), the cyclo­hexene ring is in a half-chair conformation. The dihedral angles between the mean planes of the fluoro- and chloro-substituted benzene rings are 89.9 (7) (only the major component is considered for A) and 76.4 (7)° (B). In the crystal, inversion dimers are observed along with weak C—H⋯O hydrogen bonds, which form chains along [100].
PMCID: PMC3885083  PMID: 24454259
22.  2-Methyl­aspartic acid monohydrate 
The title compound, C5H9NO4·H2O, is an isomer of the α-amino acid glutamic acid that crystallizes from water in its zwitterionic form as a monohydrate. It is not one of the 20 proteinogenic α-amino acids that are used in living systems and differs from the natural amino acids in that it has an α-methyl group rather than an α-H atom. In the crystal, an O—H⋯O hydrogen bond is present between the acid and water mol­ecules while extensive N—H⋯O and O—H⋯O hydrogen bonds link the components into a three-dimensional array.
PMCID: PMC3885094  PMID: 24454270
23.  Isovaline monohydrate 
The title compound, C5H11NO2·H2O, is an isomer of the α-amino acid valine that crystallizes from water in its zwitterion form as a monohydrate. It is not one of the 20 proteinogenic amino acids that are used in living systems and differs from the natural amino acids in that it has no α-H atom. The compound exhibits hydrogen bonding between the water mol­ecule and the carboxyl­ate O atoms and an amine H atom. In addition, there are inter­molecular hydrogen-bonding inter­actions between the carboxyl­ate O atoms and amine H atoms. In the crystal, these extensive N—H⋯O and O—H⋯O hydrogen bonds lead to the formation of a three-dimensional network.
PMCID: PMC3885077  PMID: 24454253
24.  2-(Phenyl­selenon­yl)pyridine 
In the title compound, C11H9NO2Se, the pyridine and phenyl rings are almost perpendicular, with the dihedral angle between their mean planes being 79.16 (7)°. In the crystal, the mol­ecules pack so as to form ruffled sheets in the (110) plane connected by weak C—H⋯O inter­actions. In addition, there are weak π–π inter­actions between the mean planes of both the phenyl [centroid–centroid perpendicular distance of 3.591 (2) Å and slippage of 1.854 (2) Å] and pyridine rings [centroid–centroid perpendicular distance of 3.348 (2) Å and slippage of 1.854 (2) Å].
PMCID: PMC3885055  PMID: 24454231
25.  3-[1-(4-Bromo­phen­yl)eth­oxy]-2,2,5-trimethyl-4-phenyl-3-aza­hexa­ne 
The title compound, C22H30BrNO, is an alk­oxy­amine compound, an effective initiator in nitroxide-mediated free radical polymerization. It was prepared as a mixture of two diasteromers; the crystal for the X-ray analysis showed one of these as a pair of R,S and S,R enanti­omers. The tert-butyl and isopropyl groups are in an almost anti conformation in the crystal [C—N—C—C torsion angle = −168.8 (1)°], and the methyl group of the ethoxy group is in an approximate anti relationship to the tert-butyl group. The dihedral angle between the phenyl and benzene rings is 33.12 (7)°. The Br atom is disordered over two positions, with occupancies of 0.9139 (16) and 0.0861 (16). In the crystal, weak C—H⋯Br contacts link the mol­ecules into chains along [-110].
PMCID: PMC3885056  PMID: 24454232

Results 1-25 (219)