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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.  1-[5-(4-Bromo­phen­yl)-3-(4-fluoro­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone 
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
5.  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
6.  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
7.  3-(4-Bromo­phen­yl)-5-[4-(dimethyl­amino)­phen­yl]-4,5-dihydro-1H-pyrazole-1-carbothio­amide 
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
8.  3,5-Bis(4-bromo­phen­yl)-1-phenyl-4,5-dihydro-1H-pyrazole 
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
10.  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
11.  Dimethyl 4-(3,4-dimethoxy­phen­yl)-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
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
12.  Diethyl 4-(2,4-dichloro­phen­yl)-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
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
13.  Diethyl 4-[4-(dimethyl­amino)phen­yl]-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
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
14.  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
15.  1,1′-[4-(4-Methoxy­phen­yl)-2,6-dimethyl-1,4-dihydro­pyridine-3,5-di­yl]diethanone 
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
16.  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
17.  1′-(4-Bromo­phen­yl)-4′-{4-[(2-oxo-1,2,3,4-tetra­hydro­naphthalen-2-yl­idene)meth­yl]phen­yl}-3′′,4′′-dihydro­acenaphthylene-1-spiro-2′-pyrrolidine-3′-spiro-2′′-naphthalene-2,1′′(1H,2′′H)-dione 
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
18.  Dimethyl 4-(4-ethoxy­phen­yl)-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
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
19.  Dimethyl 4-(3-hydroxy­phen­yl)-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
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
20.  Diethyl 2,6-dimethyl-4-phenyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
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
21.  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
22.  Diethyl 4-[5-(4-chloro­phen­yl)-1H-pyrazol-4-yl]-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
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
23.  7-Methyl-9-p-tolyl-4,9-dihydro­furo[3,4-b]quinolin-1(3H)-one 
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
24.  3-(4-Bromo­phen­yl)-3-(4-hydr­oxy-6-oxo-1,6-dihydro­pyrimidin-5-yl)-N-[(S)-1-phenyl­ethyl]propanamide 
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
25.  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

Results 1-25 (203801)