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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
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
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
In the title molecule, C17H14BrFN2O, the benzene rings form dihedral angles of 6.58 (6) and 85.31 (6)° with the mean plane of the 4,5-dihydro-1H-pyrazole ring (r.m.s. deviation = 0.0231 Å). The latter ring is planar with a maximum deviation of 0.032 (1) Å The dihedral angle between the benzene rings is 78.75 (6)°. In the crystal, weak C—H⋯O and C—H⋯F hydrogen bonds link the molecules into corrugated layers parallel to the ab plane.
doi:10.1107/S1600536812033351
PMCID: PMC3415024
PMID: 22905011
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
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
The molecule of the title pyrazole derivative, C18H19BrN4S, is twisted. The central pyrazole ring, which adopts a flattened envelope conformation, is almost coplanar with the 4-bromophenyl ring, whereas it is inclined to the 4-(dimethylamino)phenyl ring making dihedral angles of 1.68 (6) and 85.12 (6)°, respectively. The dihedral angle between the two benzene rings is 86.56 (6)°. The dimethylamino group is slightly twisted from the attached benzene ring [C—C—N—C torsion angles = 8.4 (2) and 8.9 (2)°]. In the crystal, molecules are linked by intermolecular N—H⋯S hydrogen bonds into chains along [20]. The crystal is further stabilized by C—H⋯π interactions.
doi:10.1107/S1600536811006106
PMCID: PMC3052174
PMID: 21522446
In the title compound, C21H16Br2N2, the central pyrazole ring adopts an flattened envelope conformation, with the stereogenic C atom in the flap position. The deviations from planarity for this ring are relatively minor (r.m.s. deviation = 0.045 Å) and the dihedral angles formed with the N- and Cimine-bound benzene rings are 7.73 (13) and 11.00 (13)°, respectively. By contrast, the benzene ring bound at the chiral C atom is almost orthogonal to the rest of the molecule; the dihedral angle formed between this ring and the pyrazole ring is 79.53 (13)°. In the crystal, the packing is stabilized by C—H⋯N and C—H⋯Br interactions.
doi:10.1107/S1600536810015795
PMCID: PMC2979444
PMID: 21579379
9.
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
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
In the title compound, C19H23NO6, the 1,4-dihydropyridine ring is twisted slightly from planarity, with a maximum deviation of 0.101 (1) Å, and adopts a very flattened boat conformation. The dihedral angle formed between the plane through the four C atoms of the 1,4-dihydropyridine ring and the benzene ring is 84.67 (7)°. In the crystal structure, intermolecular N—H⋯O and C—H⋯O hydrogen bonds link the molecules into a three-dimensional network.
doi:10.1107/S160053681001679X
PMCID: PMC2979474
PMID: 21579441
In the title compound, C19H21Cl2NO4, the dihydropyridine ring adopts a flattened boat conformation. The dichlorophenyl ring is oriented almost perpendicular to the planar part of the dihydropyridine ring [dihedral angle = 89.1 (1)°]. An intramolecular C—H⋯O hydrogen bond is observed. In the crystal structure, molecules are linked into chains along the b axis by N—H⋯O hydrogen bonds
doi:10.1107/S1600536810001066
PMCID: PMC2979797
PMID: 21579787
In the title compound, C21H28N2O4, the dihydropyridine ring adopts a flattened boat conformation. The mean plane of the dihydropyridine ring and the attached benzene ring form a dihedral angle of 85.1 (1) Å. One of two ethyl fragments is disordered between two conformations in a 0.67 (4):0.33 (4) ratio. In the crystal structure, molecules related by translation along the a axis are linked into chains via intermolecular N—H⋯O hydrogen bonds.
doi:10.1107/S1600536810003508
PMCID: PMC2983663
PMID: 21580293
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
In the title compound, C18H21NO3, which belongs to the family of calcium channel blockers, the dihydropyridine ring assumes a flattened boat conformation. The two carbonyl units adopt a synperiplanar conformation with respect to the double bonds in the dihydropyridine ring. The methoxyphenyl ring is almost perpendicular to the prydine ring [dihedral angle = 89.01 (7)°]. In the crystal, the molecules are connected by intermolecular N—H⋯O hydrogen bonds.
doi:10.1107/S1600536809041592
PMCID: PMC2971090
PMID: 21578387
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
In the title compound, C47H34BrNO3, the central benzene ring makes a dihedral angle of 42.71 (7)° with the bromophenyl ring. The pyrrolidine ring adopts an envelope conformation. The molecular structure is stabilized by weak intramolecular C—H⋯O interactions and the crystal packing is stabilized by weak intermolecular C—H⋯π interactions.
doi:10.1107/S1600536810040171
PMCID: PMC3009035
PMID: 21588996
In the title molecule, C19H23NO5, the dihedral angle formed by the benzene ring and the planar part of the dihydropyridine ring is 83.52 (5)°. The dihydropyridine ring adopts a flattened boat conformation. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, generating chains running parallel to [100]. The crystal structure is consolidated by C—H⋯O contacts.
doi:10.1107/S1600536809033364
PMCID: PMC2969859
PMID: 21577652
The 1,4-dihydropyridine ring in the title compound, C17H19NO5, has a flattened-boat conformation, and the benzene ring is almost orthogonal to it [dihedral angle = 82.98 (12)°]. The hydroxy group is disordered over two positions in a 0.780 (4):0.220 (4) ratio. In the crystal, hydrogen-bonding interactions of the type Na—H⋯Oc and Oh—H⋯Oc (a = amine, c = carbonyl and h = hydroxy) link the molecules into a three-dimensional network.
doi:10.1107/S1600536810011268
PMCID: PMC2983893
PMID: 21580781
The title molecule, C19H23NO4, was synthesized by the reaction of benzaldehyde, ethyl acetoacetate and NH4HCO3. The dihydropyridine ring adopts a flattened boat conformation and the plane of the base of the boat forms a dihedral angle of 88.78 (9)° with the phenyl ring. The packing is stabilized by strong intermolecular N—H⋯O and weak intermolecular C—H⋯O hydrogen bonds.
doi:10.1107/S1600536809009118
PMCID: PMC2969073
PMID: 21582523
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
In the title compound, C22H24ClN3O4, intramolecular C—H⋯O and C—H⋯N hydrogen bonds form S(9) and S(7) ring motifs, respectively. The 1,4-dihydropyridine ring adopts a flattened boat conformation. The benzene ring makes a dihedral angle of 33.36 (6)° with the pyrazole ring. In the crystal, pairs of N—H⋯N hydrogen bonds link the molecules into inversion dimers. The dimers are stacked in column along the a axis through N—H⋯O and C—H⋯N hydrogen bonds. The crystal packing also features C—H⋯π interactions involving the pyrazole ring.
doi:10.1107/S160053681201344X
PMCID: PMC3344438
PMID: 22590200
In the title compound, C19H17NO2, the dihydropyridine ring adopts a flattened boat conformation while the furanone ring is almost planar (r.m.s. deviation 0.018 Å). The molecules are linked into chains along the b axis by N—H⋯O intermolecular hydrogen bonds. In addition, C—H⋯π interactions involving the phenyl ring of the tolyl group as π acceptor are observed.
doi:10.1107/S1600536808041457
PMCID: PMC2968025
PMID: 21581564
In the molecule of the title compound, C21H20BrN3O3, the pyrimidine ring is oriented at dihedral angles of 80.87 (3) and 15.99 (3)°, respectively, to the pyrimidine and bromophenyl rings. The dihedral angle between the two benzene rings is 88.37 (3)°. In the crystal structure, intermolecular N—H⋯O and O—H⋯N hydrogen bonds link the molecules. A π–π contact between pyrimidine and phenyl rings [centroid–centroid distance = 3.776 (3) Å] may further stabilize the structure. The methine H and the methyl C and H atoms are disordered over two positions and were refined with occupancies of 0.522 (13) and 0.478 (13).
doi:10.1107/S1600536809003821
PMCID: PMC2968538
PMID: 21582156
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