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1.  Dimethyl 4-(4-hy­droxy­phen­yl)-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
The title mol­ecule, C17H19NO5, was prepared by a Hantzsch dihydro­pyridine synthesis from 4-hy­droxy­benzaldehyde, methyl acetoacetate and NH4HCO3. In the mol­ecular structure of the title compound, the dihydro­pyridine ring adopts a flattened boat conformation and the plane of the base of the boat forms a dihedral angle of 80.8 (2)° with the aromatic six-membered ring. The packing is stabilized by strong inter­molecular N—H⋯Ocarbon­yl, Ohydrox­y—H⋯Ocarbon­yl and weak intra­molecular C—H⋯O hydrogen bonds.
doi:10.1107/S1600536811032521
PMCID: PMC3200733  PMID: 22064645
2.  1-(4-Bromo­phen­yl)-2-ethyl­sulfinyl-2-(phenyl­selan­yl)ethanone monohydrate 
In the title hydrate, C16H15BrO2SSe·H2O, the sulfinyl O atom lies on the opposite side of the mol­ecule to the Se and carbonyl O atoms. The benzene rings form a dihedral angle of 51.66 (17)° and are splayed with respect to each other. The observed conformation allows the water mol­ecules to bridge sulfinyl O atoms via O—H⋯O hydrogen bonds, generating a linear supra­molecular chain along the b axis; the chain is further stabilized by C—H⋯O contacts. The chains are held in place in the crystal structure by C⋯H⋯π and C—Br⋯π inter­actions.
doi:10.1107/S1600536811012712
PMCID: PMC3089188  PMID: 21754419
3.  Ethyl [1-(4-bromo­phen­yl)-1-hydr­oxy-3-oxobut­yl](phen­yl)phosphinate monohydrate1  
In the title hydrate, C18H20BrO4P·H2O, a staggered conformation is found when the organic mol­ecule is viewed down the central P—C bond, with the oxo and hydroxyl groups being diagonally opposite; each of the central P and C atoms has an S-configuration. The crystal structure features supra­molecular double chains along the b axis mediated by Ohydrox­yl–H⋯Ooxo, Owater–H⋯Ooxo, and Owater–H⋯Owater hydrogen bonds.
doi:10.1107/S160053681000437X
PMCID: PMC2983684  PMID: 21580337
4.  9-(3-Bromo-5-chloro-2-hy­droxy­phen­yl)-10-(2-hy­droxy­eth­yl)-1,2,3,4,5,6,7,8,9,10-deca­hydro­acridine-1,8-dione 
In the title compound, C21H21BrClNO4, the dihydro­pyridine ring adopts a flattened boat conformation. The 3-bromo-5-chloro-2-hy­droxy­phenyl ring forms a dihedral angles of 84.44 (7)° with the dihydro­pyridine mean plane. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯O hydrogen bond, with an S(8) ring motif. In the crystal, O—H⋯O and C—H⋯O hydrogen bonds link the mol­ecules, forming a three-dimensional network.
doi:10.1107/S1600536812050222
PMCID: PMC3588342  PMID: 23476467
5.  6-(4-Bromo­phen­yl)-2-eth­oxy-4-(2,4,6-trimethoxy­phen­yl)nicotinonitrile1  
In the asymmetric unit of the title nicotinonitrile derivative, C23H21BrN2O4, there are two non-planar independent mol­ecules. The central pyridine ring makes dihedral angles of 9.05 (7) and 77.06 (7)°, respectively, with the 4-bromo­phenyl and 2,4,6-trimethoxy­phenyl rings in one mol­ecule, whereas the corresponding values are 5.96 (7) and 82.37 (7)° in the other. All the three meth­oxy groups are essentially in the plane of the attached benzene ring [C—O—C—C angles = 2.99 (19), 4.8 (2) and −6.2 (2)° in one mol­ecule, and 2.69 (18), 176.73 (15) and 1.3 (2)° in the other]. The eth­oxy group is slightly twisted in one mol­ecule [C—C—O—C = 173.84 (12)°], whereas it is coplanar with the pyridine ring in the other [C—C—O—C = −177.23 (13)°]. Weak intra­molecular C—H⋯N inter­actions generate S(5) ring motifs. In the crystal structure, the mol­ecules are linked by weak inter­molecular C—H⋯N and C—H⋯O inter­actions into a supra­molecular three-dimensional network in such a way that the nicotinonitrile units of neighboring mol­ecules are stacked in an anti­parallel manner along the c axis. The crystal is further stabilized by C—H⋯π inter­actions.
doi:10.1107/S1600536809043943
PMCID: PMC2971038  PMID: 21578493
6.  Crystal structure of 5,5-bis­(4-methyl­benz­yl)pyrimidine-2,4,6(1H,3H,5H)-trione monohydrate 
Reaction of 4-methyl benzyl chloride with barbituric acid gave 5,5-bis­(4-methyl­benz­yl)pyrimidine-2,4,6(1H,3H,5H)-trione, which crystallized with two mol­ecules in its asymmetric unit along with two solvent water mol­ecules. A hydrogen-bonded sheet is formed by a combination of N—H⋯O and Owater—H⋯O hydrogen bonds, which are further inter­connected by C—H⋯πar­yl inter­actions, leading to a three-dimensional supra­molecular architecture.
The asymmetric unit of the title compound, C20H20N2O3·H2O, contains two independent mol­ecules (A and B), with similar conformations and two independent water mol­ecules. In the crystal, N—H⋯O and Owater—H⋯O hydrogen bonds link all moieties into two crystallographically independent kinds of sheets parallel to the ac plane. These independent sheets, each containing either A or B mol­ecules, are further alternately stacked along the b axis and inter­connected via C—H⋯πar­yl inter­actions.
doi:10.1107/S205698901402619X
PMCID: PMC4331871
crystal structure; hydrogen-bonded sheets; pyrimidine; C—H⋯π inter­actions; Knoevenagel condensation; three-dimensional structure
7.  Solid-state tautomeric structure and invariom refinement of a novel and potent HIV integrase inhibitor 
The conformation and tautomeric structure of (Z)-4-[5-(2,6-difluoro­benzyl)-1-(2-fluoro­benzyl)-2-oxo-1,2-dihydro­pyridin-3-yl]-4-hy­droxy-2-oxo-N-(2-oxopyrrolidin-1-yl)but-3-enamide, C27H22F3N3O5, in the solid state has been resolved by single-crystal X-ray crystallography. The electron distribution in the mol­ecule was evaluated by refinements with invarioms, aspherical scattering factors by the method of Dittrich et al. [Acta Cryst. (2005), A61, 314–320] that are based on the Hansen–Coppens multipole model [Hansen & Coppens (1978 ▶). Acta Cryst. A34, 909–921]. The β-diketo portion of the mol­ecule exists in the enol form. The enol –OH hydrogen forms a strong asymmetric hydrogen bond with the carbonyl O atom on the β-C atom of the chain. Weak intra­molecular hydrogen bonds exist between the weakly acidic α-CH hydrogen of the keto–enol group and the pyridinone carbonyl O atom, and also between the hydrazine N—H group and the carbonyl group in the β-position from the hydrazine N—H group. The electrostatic properties of the mol­ecule were derived from the mol­ecular charge density. The mol­ecule is in a lengthened conformation and the rings of the two benzyl groups are nearly orthogonal. Results from a high-field 1H and 13C NMR correlation spectroscopy study confirm that the same tautomer exists in solution as in the solid state.
doi:10.1107/S0108270113003806
PMCID: PMC3589111  PMID: 23459357
8.  1-(4-Bromo­phen­yl)-2-(phenyl­sulfon­yl)ethanone 
The overall conformation of the title mol­ecule, C14H11BrO3S, is L-shaped, as seen in the value of the dihedral angle formed between the terminal benzene rings of 75.44 (13)°. The presence of C—H⋯O inter­actions leads to the formation of linear supra­molecular chains along the a-axis direction in the crystal structure. These are connected into supra­molecular arrays in the ab plane via C—H⋯π contacts.
doi:10.1107/S1600536811036671
PMCID: PMC3201297  PMID: 22064893
9.  N-[3a-(4-Bromo­phen­yl)-8b-hy­droxy-6,8-dimeth­oxy-3-phenyl-2,3,3a,8b-tetra­hydro-1H-cyclo­penta­[b]benzofuran-1-yl]formamide monohydrate 
In the title compound, C26H24BrNO5·H2O, a synthetic analogue of natural flavagline, the cyclo­pentane ring adopts an envelope conformation (the flap atom bearing the phenyl group) and the vicinal phenyl and bromo­phenyl groups are slightly shifted relative to each other [CPh—C—C—CPhBr = 36.3 (2)°]. Intra­molecular N—H⋯O and C—H⋯O hydrogen bonds form S(5) motifs. In the crystal, the organic and the water mol­ecules are linked by an O—H⋯O hydrogen bond. Pairs of organic and water mol­ecules, located about inversion centers, inter­act through O—H⋯O hydrogen bonds, forming R 4 4(20) and R 4 4(26) motifs, which together lead to C 2 2(9) motifs. The crystal packing is also characterized by N—H⋯O and C—H⋯O hydrogen bonds between neighbouring organic mol­ecules, forming R 2 2(10) and R 2 2(18) motifs, respectively.
doi:10.1107/S1600536812049641
PMCID: PMC3588239  PMID: 23476436
10.  Dimethyl 4-(4-formyl­phen­yl)-2,6-di­methyl-1,4-dihydro­pyridine-3,5-dicar­boxyl­ate 
The title compound, C18H19NO5, is a product of the Hantzsch reaction of p-phthalaldehyde, methyl acetoacetate, and ammonium acetate. The 1,4-dihydro­pyridine ring of the mol­ecule adopts a flattened boat conformation. The benzene ring is almost perpendicular to the 1,4-dihydro­pyridine ring; the plane through the six C atoms of the benzene ring and the plane through the four C atoms that form the base of the boat-shaped 1,4-dihydro­pyridine ring (excluding the ring N atom and the opposite ring C atom) make a dihedral angle of 87.60 (3)°. Inter­molecular N—H⋯O hydrogen bonds result in the formation of extended chains along the a axis.
doi:10.1107/S1600536807063428
PMCID: PMC2915344  PMID: 21200858
11.  Diethyl 2,6-dimethyl-4-(5-phenyl-1H-pyrazol-4-yl)-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
In the title compound, C22H25N3O4, the dihydro­pyridine ring adopts a flattened boat conformation. The pyrazole ring makes a dihedral angle of 29.04 (5)° with the benzene ring. The mol­ecular structure is stabilized by an intra­molecular C—H⋯O hydrogen bond which generates an S(9) ring motif. In the crystal, mol­ecules are linked via N—H⋯O and C—H⋯N hydrogen bonds into a two-dimensional network parallel to the ab plane. The crystal structure is further consolidated by weak C—H⋯π inter­actions.
doi:10.1107/S1600536812008173
PMCID: PMC3297939  PMID: 22412742
12.  Ethyl 2-methyl-5-oxo-4-(3,4,5-trimeth­oxy­phen­yl)-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate 
In the mol­ecular structure of the title compound, C22H27NO6, the dihydro­pyridine ring adopts a flattened boat conformation while the cyclo­hexenone ring is in an envelope conformation. In the crystal, mol­ecules stack parallel to the crystallographic a axis linked by inter­molecular N—H⋯O and C—H⋯O hydrogen bonds.
doi:10.1107/S1600536810030333
PMCID: PMC3008019  PMID: 21588607
13.  1,1′-[4-(2,4-Dichloro­phen­yl)-2,6-di­methyl-1,4-di­hydro­pyridine-3,5-di­yl]diethanone 
In the title compound, C17H17Cl2NO2, the central 1,4-dihydro­pyridine ring adopts a flattened-boat conformation. The ethanone substituents of the dihydro­pyridine ring at positions 3 and 5 have synperiplanar (cis) or anti­periplanar (trans) conformations with respect to the adjacent C=C bonds in the dihydro­pyridine ring. The 2,4-dichloro­phenyl ring is almost planar [r.m.s. deviation = 0.0045 (1) Å] and almost perpendicular [89.27 (3)°] to the mean plane of the dihydro­pyridine ring. In the crystal, an N—H⋯O hydrogen bond links mol­ecules into a zigzag chain along the ac diagonal. C—H⋯Cl contacts form centrosymmetric dimers and additional weak C—H⋯O contacts further consolidate the packing.
doi:10.1107/S1600536810052839
PMCID: PMC3051630  PMID: 21523057
14.  Ethyl 4-(3-hydroxy­phen­yl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate 
In the mol­ecular structure of the title compound, C21H25NO4, the dihydro­pyridine ring adopts a flattened boat conformation while the cyclo­hexenone ring is in an envelope conformation. In the crystal structure, mol­ecules are linked into a two-dimensional network parallel to (10) by N—H⋯O and O—H⋯O hydrogen bonds. The network is generated by R 4 4(30) and R 4 4(34) graph-set motifs.
doi:10.1107/S1600536809039877
PMCID: PMC2971334  PMID: 21578275
15.  Chlorido[(E)-2-hydr­oxy-6-(isonicotinoyl­hydrazonometh­yl)phen­yl]mercury(II) monohydrate 
The asymmetric unit of the title compound, [Hg(C13H10N3O2)Cl]·H2O, contains two independent mercury(II) complexes with slightly different conformations, related via a pseudo-inversion centre, and two water mol­ecules. The HgII atoms show a typical linear geometry to a C atom of the benzene ring and to a Cl atom. A benzene C and the azomethine N atom chelate the HgII atoms with weak intra­molecular Hg⋯N bonding distances of 2.735 (3) and 2.739 (3) Å, respectively. The resulting five-membered metallacycles are nearly coplanar with the benzene rings [dihedral angles = 0.9 (1) and 0.7 (1)°], while the pyridine rings make dihedral angles with the benzene units of 58.17 (1) and 56.58 (1)°. In the crystal structure, the HgII complexes are linked by hydr­oxy donor and pyridine acceptor groups into chains along [010]. The water mol­ecules connect the complexes through inter­molecular O—H⋯Ocarbon­yl bonds in the a-axis direction, and the azomethine H atoms donate towards the water O atoms, forming a three-dimensional network of inter­molecular O—H⋯N, O—H⋯O and N—H⋯O hydrogen bonds.
doi:10.1107/S1600536809023824
PMCID: PMC2969284  PMID: 21582756
16.  (1E)-1-(3-Bromo­phen­yl)ethanone 2,4-di­nitro­phenyl­hydrazone 
The title compound, C14H11BrN4O4, contains 3-bromo­phenyl and 2,4-dinitro­phenyl groups on opposite sides of a hydrazone unit and crystallizes with two mol­ecules in the asymmetric unit. The dihedral angles between the two ring systems in each mol­ecule are 2.0 (1) and 2.5 (4)°. Weak C—H⋯O hydrogen bonds and weak π–π stacking inter­actions [centroid–centroid distance = 3.7269 (14) Å] help to establish the packing. Intra­molecular N—H⋯O hydrogen bonds are also observed. On one of the rings, the Br atom is disordered over two equivalent positions of the phenyl ring [occupancy ratio 0.8734 (10):0.1266 (10).
doi:10.1107/S1600536810037980
PMCID: PMC3008979  PMID: 21589019
17.  N-(3-Bromo­phen­yl)acetamide 
The conformation of the N—H bond in the structure of the title compound, C8H8BrNO, is anti to the C=O bond and to the meta-bromo substituent of the aromatic ring in both independent mol­ecules comprising the asymmetric unit. Mol­ecules are linked through N—H⋯O hydrogen bonding into supra­molecular chains with a twisted topology.
doi:10.1107/S1600536809013294
PMCID: PMC2977722  PMID: 21583858
18.  1-[(4-Bromo­phen­yl)(morpholin-4-yl)meth­yl]naphthalen-2-ol 
The title compound, C21H20BrNO2, was obtained from a condensation reaction of 4-bromo­benzaldehyde, 2-naphthol and morpholine. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯N hydrogen bond, closing a six-membered ring. The dihedral angle between the naphthalene ring system and the benzene ring is 76.72 (8)°. In addition to the intra­molecular hydrogen bond, the O—H groups of centrosymmetrically related mol­ecules form short inter­molecular H⋯O contacts of 2.59 Å. These mol­ecules are also linked by pairs of C—H⋯O inter­actions, generating an R 2 2(14) motif.
doi:10.1107/S1600536812002620
PMCID: PMC3275269  PMID: 22347125
19.  2-(Benzo[d]thia­zol-2-ylsulfon­yl)-1-(4-bromo­phen­yl)ethanone 
In the title mol­ecule, C15H10BrNO3S2, the dihedral angle between the benzothia­zole ring system and the benzene ring is 67.57 (12)°. The crystal structure is stabilized by weak inter­molecular C—H⋯O inter­actions. In addition, there is an inter­molecular Br⋯C [3.379 (3) Å] contact which is shorter than the sum of the van der Waals radii of these atoms.
doi:10.1107/S1600536809053112
PMCID: PMC2980183  PMID: 21580093
20.  Diisobutyl 4-(3-eth­oxy-4-hy­droxy­phen­yl)-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
The asymmetric unit of the title compound, C25H35NO6, contains two independent mol­ecules. In each mol­ecule, the 1,4-dihydro­pyridine ring adopts a flattened boat conformation. The dihedral angles between the 1,4-dihydro­pyridine and benzene rings are 87.55 (7) and 87.23 (7)°. In one of these mol­ecules, one of the isobutyl groups is disordered over two sets of sites, with an occupancy ratio of 0.890 (2):0.110 (2). In the crystal, mol­ecules are linked through N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds forming two-dimensional networks parallel to the ab plane. The crystal structure is further stabilized by weak C—H⋯π inter­actions.
doi:10.1107/S1600536811055334
PMCID: PMC3274982  PMID: 22346927
21.  4-Amino-2,3,5-trimethyl­pyridine monohydrate 
In the title compound, C8H12N2·H2O, four substituted pyridine mol­ecules alternate with four water mol­ecules, forming a large ring via Owater—H⋯Npyridine and Namine—H⋯Owater hydrogen bonding. Adjacent rings are connected via Owater—H⋯Owater hydrogen-bonds, forming a three-dimensional network.
doi:10.1107/S1600536809016833
PMCID: PMC2969585  PMID: 21583183
22.  1-Methyl-3,5-bis­[(E)-(3-methyl-2-thienyl)methyl­ene]piperidin-4-one monohydrate 
In the title mol­ecule, C18H19NOS2·H2O, the piperidine ring adopts an envelope conformation with the methyl substituent in an equatorial position. Each of the olefinic double bonds has an E configuration. The dihedral angle between the two thio­phene rings is 6.04 (14)°. The water mol­ecule forms two donor inter­actions, one with the carbonyl O atom and the other to the hetero N atom. The centrosymmetric {C18H19NOS2·H2O}2 pairs thus formed are linked into a supra­molecular chain via C—H⋯Owater contacts.
doi:10.1107/S1600536809010393
PMCID: PMC2968964  PMID: 21582594
23.  4-(4-Chloro­phen­yl)-2,6-bis­(1H-indol-3-yl)-1,4-dihydro­pyridine-3,5-dicarbo­nitrile ethanol monosolvate 
In the title compound, C29H18ClN5·C2H6O, the dihydro­pyridine ring adopts a strongly flattened envelope conformation, with a maximum deviation of 0.139 (2) Å from its best plane for the Csp 3 atom. The dihedral angles between the dihydro­pyridine ring plane and the two indole rings in positions 2 and 6 are 34.28 (5) and 40.50 (6)°, respectively. In turn, the benzene ring and the dihydro­pyridine ring are oriented at a dihedral angle of 74.69 (6)°. An intra­molecular C—H⋯Cl hydrogen bond occurs. In the crystal, mol­ecules are linked by N—H⋯N, N—H⋯O and O—H⋯N hydrogen bonds into layers parallel to (001). There are short C—H⋯Cl contacts between mol­ecules in neighboring layers.
doi:10.1107/S1600536812013906
PMCID: PMC3344446  PMID: 22590208
24.  2-{[3-Methyl-4-(2,2,2-trifluoro­eth­oxy)pyridin-2-yl]methyl­sulfan­yl}-1H-benzimidazole monohydrate 
The asymmetric unit of the title compound, C16H14F3N3OS·H2O, contains two independent mol­ecules (A and B) and two water mol­ecules, one of which is disordered over two positions in a 0.790 (8):0.210 (8) ratio. The mol­ecular conformations are close, the benzimidazole mean plane and pyridine ring forming dihedral angles of 1.8 (3) and 0.1 (2)° in mol­ecules A and B, respectively. The water mol­ecules are involved in formation of two independent hydrogen-bonded chains via N—H⋯O and O—H⋯N hydrogen bonds. Chains propagating along the a axis are formed by mol­ecule A and one independent water mol­ecule, while chains propagating along the b axis are formed by mol­ecule B and the other independent water mol­ecule. The crystal packing exhibits π–π inter­actions, as indicated by short distances of 3.607 (3) and 3.701 (3) Å between the centroids of the imidazole and pyridine rings of neighbouring mol­ecules.
doi:10.1107/S1600536810053730
PMCID: PMC3051707  PMID: 21522962
25.  4′-(4-Bromo­phen­yl)-1′-methyl­dispiro­[acenaphthyl­ene-1,2′-pyrrolidine-3′,2′′-indane]-2,1′′(1H)-dione 
In the title compound, C30H22BrNO2, the cyclo­pentane ring of the dihydro­acenaphthyl­ene group and the pyrrolidine ring are both in envelope conformations with the spiro C atom and N atom, respectively, as the flap atom. The cyclo­pentane ring of the indane group adopts a half-chair conformation. A weak intra­molecular C—H⋯O hydrogen bond forms an S(8) ring motif. The naphthalene ring system of the dihydro­acenaphthyl­ene group forms dihedral angles of 41.76 (6) and 42.17 (6)° with the benzene ring of the bromo­phenyl group and the benzene ring of the indane group, respectively. The dihedral angle between the two benzene rings is 83.92 (7)°. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯N hydrogen bonds into a two-dimensional network parallel to the ac plane. Weak C—H⋯π inter­actions are also observed.
doi:10.1107/S1600536812014213
PMCID: PMC3344476  PMID: 22590238

Results 1-25 (293053)