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1.  8-Bromo-3-(4-ethyl­phen­yl)-1-phenyl-3,3a,4,9b-tetra­hydro-1H-chromeno[4,3-c]isoxazole-3a-carbo­nitrile 
In the title compound, C25H21BrN2O2, the fused isoxazolidine ring adopts an envelope conformation with the N atom at the flap and the mean plane of the ring makes dihedral angles of 54.37 (12) and 87.32 (13)°, respectively, with the adjacent phenyl and benzene rings. The tetra­hydro­pyran ring has a half-chair conformation. In the crystal, mol­ecules are linked into a double-column structure along the b-axis direction through weak C—H⋯O and C—H⋯π inter­actions.
doi:10.1107/S1600536813023982
PMCID: PMC3790401  PMID: 24098220
2.  (E)-2-Bromo­methyl-3-(o-tol­yl)acrylo­nitrile 
The title compound C11H10BrN, has an E conformation at the C=C bond of the acrylo­nitrile unit. The vinyl group makes a dihedral angle of 44.53 (12)° with the benzene ring. In the crystal, weak C—H⋯π inter­actions involving the benzene ring are observed.
doi:10.1107/S1600536813021041
PMCID: PMC3884406  PMID: 24427013
3.  (E)-2-[(2-Formyl­phen­oxy)meth­yl]-3-(4-iso­propyl­phen­yl)acrylo­nitrile 
In the title compound, C20H19NO2, the dihedral angle between the benzene rings is 77.12 (8)°. The terminal isopropyl group is disordered over two orientations, with site occupancies of 0.720 (14) and 0.280 (14). In the crystal, mol­ecules are linked through a weak C—H⋯O inter­action, forming a zigzag chain along the c-axis direction.
doi:10.1107/S1600536813020618
PMCID: PMC3793832  PMID: 24109419
4.  Methyl 3′-benzyl-4′-(2-chloro­phen­yl)-1′-methyl-2-oxo­spiro­[indoline-3,2′-pyrrolidine]-3′-carboxyl­ate 
In the title compound, C27H25ClN2O3, the methyl­pyrrolidine ring adopts an envelope conformation with the N atom at the flap. The mean plane of the pyrrolidine ring makes dihedral angles of 82.1 (1), 84.4 (1) and 79.8 (1)°, respectively, with the adjacent benzene ring, the mean plane of the indoline ring system and the phenyl ring. The mol­ecular structure is stabilized by intra­molecular C—H⋯O hydrogen bonds. In the crystal, mol­ecules are linked into chains along [101] by N—H⋯O hydrogen bonds. C—H⋯π inter­actions are observed between the chains.
doi:10.1107/S1600536813018424
PMCID: PMC3793722  PMID: 24109309
5.  14-Meth­oxy-4,6-dimethyl-9-phenyl-8,12-dioxa-4,6-di­aza­tetra­cyclo­[8.8.0.02,7.013,18]octa­deca-2(7),13,15,17-tetra­ene-3,5,11-trione 
The title compound, C23H20N2O6, crystallizes with two mol­ecules in the asymmetric unit in which the dihedral angles between the mean planes of the pyran and phenyl rings are 66.6 (1) and 61.9 (1) °. The fused pyrone and pyran rings each adopts a sofa conformation. In the crystal, C—H⋯O hydrogen bonds link the mol­ecules, forming a two-dimensional network parallel to [001].
doi:10.1107/S1600536813017789
PMCID: PMC3793711  PMID: 24109298
6.  Methyl 2-[(2-chloro­quinolin-3-yl)(hy­droxy)meth­yl]acrylate 
There are two independent mol­ecules (A and B) in the asymmetric unit of the title compound, C14H12ClNO3. The mean planes of the methyl ester unit (Cmeth­yl—O—C=O; r.m.s. deviation = 0.051 Å for mol­ecule A and 0.016 Å for mol­ecule B) and the chloro­quilonine ring system (r.m.s. deviation = 0.023 Å for mol­ecule A and 0.014 Å for mol­ecule B) form dihedral angles of 63.5 (1)° in mol­ecule A and 78.1 (1)° in mol­ecule B. The main difference between the two independent mol­ecules is reflected in the (H)O—C—C=C(H2) torsion angle which is −109.7 (2)° in mol­ecule A and 10.6 (2)° in mol­ecule B. An intra­molecular O—H⋯O hydrogen bond is observed in mol­ecule A. In the crystal, mol­ecules A and B are linked into pairs via bifurcated O—H⋯(N,Cl) hydrogen bonds and a weak C—H⋯O hydrogen bond links pairs of mol­ecules into chains along [100].
doi:10.1107/S1600536813014050
PMCID: PMC3685122  PMID: 23795141
7.  2-[(2-Chloro­quinolin-3-yl)(hy­droxy)meth­yl]acrylo­nitrile 
In the title compound, C13H9ClN2O, the dihedral angle between the acrylo­nitrile C=C—CN plane and the quilonine ring system is 71.3 (2)°. In the crystal, mol­ecules are linked by O—H⋯N hydrogen bonds, forming chains along [01-1]. The chains are linked into a three-dimensional network through C—H⋯N inter­actions.
doi:10.1107/S1600536813010155
PMCID: PMC3648303  PMID: 23723923
8.  (Z)-3-(3,4-Di­meth­oxy­benz­yl)-1,5-benzo­thia­zepin-4(5H)-one 
In the title compound, C18H17NO3S, the thia­zepine ring adopts a slightly distorted twist-boat conformation. The dihedral angle between the mean plane of the benzo­thia­zepin ring system and the benzene ring is 60.3 (1)°. In the crystal, mol­ecules are linked by two pairs of inversion-related N—H⋯O and C—H⋯O hydrogen bonds, generating alternating R 2 2(8) and R 2 2(6) ring motifs, respectively, in a zigzag supra­molecular chain that runs along the c axis. These chains stack along the a axis via S⋯C [3.424 (2) Å] contacts. A three-dimensional supra­molecular network is consolidated by C—H⋯π and π–π inter­actions [inter-centroid distance between di­meth­oxy­benzene rings = 3.815 (1) Å]. The crystal studied was a non-merohedral twin, with a refined value of the minor twin fraction of 0.2477 (6) .
doi:10.1107/S1600536813009598
PMCID: PMC3648241  PMID: 23723861
9.  rac-3-(4-Chloro­phen­yl)-3a,4-di­hydro-3H-chromeno[4,3-c]isoxazole-3a-carbo­nitrile 
The title compound, C17H11ClN2O2, which contains two stereogenic C atoms, crystallizes in a centrosymmetric space group as a racemate. The pyran ring and the isoxazole ring adopt sofa and twisted conformations, respectively. The dihedral angle between the benzene ring and the mean plane through the near coplanar atoms of the pyran ring is 4.17 (5)°. The mol­ecular conformation features a weak C—H⋯O contact. In the crystal, C—H⋯O hydrogen bonds link the mol­ecules, forming chains along the a-axis direction.
doi:10.1107/S1600536813009653
PMCID: PMC3648249  PMID: 23723869
10.  3-(4-Methoxybenzyl)-1,5-benzo­thiazepin-4(5H)-one 
In the title compound, C17H15NO2S, the thia­zepine ring adopts a slightly distorted twist-boat conformation. The dihedral angle between the mean plane of the benzo­thia­zepin ring system and the benzene ring is 65.7 (1)°. In the crystal, pairs of N—H⋯O hydrogen bonds link inversion-related mol­ecules into dimers, generating R22(8) ring motifs. These dimers are further linked by C—H⋯π and π–π inter­actions [inter-centroid distance between the benzene rings of the benzo­thia­zepine unit = 3.656 (3) Å] into a three-dimensional supra­molecular network.
doi:10.1107/S1600536813009215
PMCID: PMC3648230  PMID: 23723850
11.  rac-Methyl 3-(2-meth­oxy­phen­yl)-3a,4-di­hydro-3H-chromeno[4,3-c]isoxazole-3a-carboxyl­ate 
The title compound, C19H17NO5, comprising two stereogenic C atoms of the same configuration, crystallizes in a centrosymmetric space group as a racemate. The pyran ring adopts a half-chair conformation, while the isoxazole ring adopts an envelope conformation with the C atom bonded to the meth­oxy­phenyl group as the flap. The dihedral angle between the mean plane of the pyran ring and the adjacent benzene ring is 5.86 (5)°. In the crystal, mol­ecules are linked by a weak C—H⋯O hydrogen bond, forming a chain along the a axis.
doi:10.1107/S1600536813008635
PMCID: PMC3647860  PMID: 23723826
12.  (Z)-3-(3,4-Dimeth­oxy­benzyl­idene)-2,3-dihydro-1,5-benzothia­zepin-4(5H)-one 
In the title compound, C18H17NO3S, the seven-membered thia­zepine ring adopts a slightly distorted sofa conformation. The dihedral angle between the mean plane of the benzothia­zepine ring system and the benzene ring is 5.9 (1)°. The mol­ecular conformation is stabilized by an intra­molecular C—H⋯S hydrogen bond, which generates an S(7) ring motif. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds link inversion-related mol­ecules into dimers, incorporating R 1 2(6) and R 2 2(8) ring motifs; the acceptor O atom is bifurcated. These dimers are further linked by C—H⋯O hydrogen bonds, forming supra­molecular tapes running along the a axis. These are connected into the three-dimensional architecture by C—H⋯π inter­actions.
doi:10.1107/S1600536813007423
PMCID: PMC3629613  PMID: 23634100
13.  (Z)-3-(2,4-Dichloro­benz­yl)-1,5-benzo­thia­zepin-4(5H)-one 
In the title compound, C16H11Cl2NOS, the seven-membered thia­zepine ring adopts a distorted twist-boat conformation. The dihedral angle between the mean plane of the benzothia­zepine ring system and the benzene ring is 78.6 (1)°. The mol­ecular conformation is stabilized by a weak intra­molecular C—H⋯Cl hydrogen bond, which generates an S(5) ring motif. In the crystal, pairs of N—H⋯O hydrogen bonds link inversion-related mol­ecules into dimers, generating R 2 2(8) ring motifs. The crystal packing also features alternating π–π inter­actions between benzothia­zepine benzene rings [inter-centroid distance = 3.740 (3) Å] and dichloro­benzene rings [inter-centroid distance = 3.882 (3) Å] to consolidate a three-dimensional architecture.
doi:10.1107/S1600536813007435
PMCID: PMC3629614  PMID: 23634101
14.  [4-(4-Meth­oxy­phen­yl)-1-methyl-3-nitro­pyrrolidin-3-yl]methanol 
In the title compound, C13H18N2O4, the dihedral angle between the benzene and pyrrolidine (all atoms) rings is 70.6 (1)°. The pyrrolidine ring adopts a half-chair conformation. In the crystal, mol­ecules form chains along the c-axis direction linked by O—H⋯N hydrogen bonds, which are then connected by C—H⋯O inter­actions, forming a sheet parallel to the bc plane.
doi:10.1107/S1600536813003073
PMCID: PMC3588458  PMID: 23476560
15.  8-Bromo-3-phenyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-carbo­nitrile 
In the title compound, C17H11BrN2O2, the five-membered isoxazole ring has an envelope conformation with the C atom bearing the phenyl ring as the flap. The pyran ring has a half-chair conformation. In the chromeno ring system, the dihedral angle between the mean plane of the pyran ring and the benzene ring is 4.68 (2)°. The dihedral angle between the mean planes of the chromeno ring system and the isoxazole ring is 13.79 (15)°. The latter forms a dihedral angle of 34.10 (17)° with the phenyl ring. In the crystal, mol­ecules are linked by C—H⋯N hydrogen bonds, forming an undulating two-dimensional network parallel to the ab plane.
doi:10.1107/S1600536813002511
PMCID: PMC3569831  PMID: 23424577
16.  14-Eth­oxy-4,6,9-trimethyl-8,12-dioxa-4,6-diaza­tetra­cyclo­[8.8.0.02,7.013,18]octa­deca-2(7),13,15,17-tetra­ene-3,5,11-trione 
In the title compound, C19H20N2O6, the pyrone and pyran rings adopt envelope conformations with the same common C atom as the flap, the dihedral angle between the planes of the remaining ring atoms being 68.27 (4)°. The planar atoms of the pyran ring and the diaza­cyclic ring are almost coplanar, the dihedral angle between their mean planes being 3.29 (7)°. Moreover, the planar atoms of the pyrone ring and benzene ring of the coumarin unit are also close to coplanar, the dihedral angle between their mean planes being 8.03 (9)°. The meth­oxy group lies in the plane of the benzene ring, with a dihedral angle between their mean planes of 9.4 (2)°. In the crystal, the molecules are linked by C—H⋯O hydrogen bonds resulting in sheets of mol­ecules in the ac plane.
doi:10.1107/S1600536813000743
PMCID: PMC3569800  PMID: 23424546
17.  Methyl 4′-(4-fluoro­phen­yl)-1′-methyl-3′-nitro­methyl-2-oxospiro­[indoline-3,2′-pyrrolidine]-3′-carboxyl­ate 
In the title compound, C21H20FN3O5, the the pyrrolidine ring makes dihedral angles of 84.91 (6) and 62.38 (7)° with the oxindole unit and the fluoro­phenyl ring, respectively. The pyrrolidine ring assumes an envelope conformation with the spiro C atom as the flap. The crystal packing features weak N—H⋯N and C—H⋯O hydrogen bonds.
doi:10.1107/S1600536813001578
PMCID: PMC3569805  PMID: 23424551
18.  (6bS*,14R*,14aR*)-Methyl 14-(4-methyl­phen­yl)-7-oxo-6b,6c,7,12b,14,14a-hexa­hydro-1H-pyrano[3,2-c:5,4-c′]dichromene-14a-carboxyl­ate 
In the title compound, C28H22O6, the chromeno ring system is almost planar, with a dihedral angle between the mean planes of the pyran and benzene rings of 1.87 (8)°. The pyran ring bearing the methyl­phenyl substituent has a half-chair conformation while the other pyran ring has an envelope conformation with the tetra­substituted C atom as the flap. The benzene ring of the chromeno ring system is inclined to the benzene ring fused to the latter pyran ring by 74.66 (9)°. These aromatic rings are inclined to the 4-methyl­phenyl ring by 52.67 (9) and 66.63 (10)°, respectively. In the crystal, mol­ecules are linked via C—H⋯O hydrogen bonds, forming a two-dimensional network parallel to the bc plane.
doi:10.1107/S1600536813001244
PMCID: PMC3569797  PMID: 23424543
19.  Methyl 6-eth­oxy-3-phenyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-car­boxylate 
In the title compound, C20H19NO5, the dihedral angle between the mean plane of the pyran ring (which has a half-chair conformation) and the benzene ring of the chromeno ring system is 7.21 (7)°. The dihedral angle between the mean plane of the chromeno ring system and the isoxazole ring is 21.78 (6)°, while the isoxazole ring forms a dihedral angle of 72.60 (8)° with the attached phenyl ring. In the crystal, mol­ecules are linked via pairs of C—H⋯O hydrogen bonds, forming inversion dimers with an R 2 2(10) ring motif. These dimers are linked via C—H⋯N hydrogen bonds, forming chains along [001].
doi:10.1107/S1600536812051720
PMCID: PMC3569242  PMID: 23424465
20.  3-(2-Methyl­phen­yl)-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-carbo­nitrile 
In the title compound, C18H14N2O2, the pyran ring of the chromeno ring system has a half-chair conformation, and the dihedral angle between its mean plane and the benzene ring is 5.3 (2)°. The isoxazole ring forms a dihedral angle of 74.6 (2)° with the attached benzene ring and is inclined to the mean plane of the chromeno ring system by 15.06 (19)°. In the crystal, there are no significant inter­molecular inter­actions.
doi:10.1107/S1600536812051732
PMCID: PMC3569243  PMID: 23424466
21.  14-Eth­oxy-4,6-dimethyl-9-phenyl-8,12-dioxa-4,6-diaza­tetra­cyclo­[8.8.0.02,7.013,18]octa­deca-2(7),13,15,17-tetra­ene-3,5,11-trione 
In the title compound, C23H20N2O6, the fused pyrone and pyran rings each adopt a sofa conformation. The dihedral angle between the mean planes of the pyran and phenyl rings is 61.9 (1)°. In the crystal, mol­ecules are linked by two pairs of C—H⋯O hydrogen bonds, forming dimers. These dimers are linked via a third C—H⋯O hydrogen bond, forming a two-dimensional network parallel to (10-2).
doi:10.1107/S160053681205009X
PMCID: PMC3588261  PMID: 23476462
22.  (E)-3-(1,3-Benzodioxol-5-yl)-2-{[N-(2-formylphenyl)-4-methylbenzenesulfon­amido]methyl}prop-2-enenitrile 
In the title compound, C25H20N2O5S, the benzodioxole ring system is essentially planar [maximum deviation = 0.021 (2) Å] and forms dihedral angles of 85.2 (1) and 74.2 (1)°, respectively, with the formyl benzene and sulfonyl-bound benzene rings. In the crystal, C—H⋯O hydrogen bonds generate C(8) chains along [100] and R33(19) ring motifs. In addition, a weak π–π inter­action [centroid–centroid distance = 3.937 (3) Å] is also observed.
doi:10.1107/S1600536812042663
PMCID: PMC3515259  PMID: 23284479
23.  Methyl (E)-2-cyano-3-(6-nitro-1,3-benzodioxol-5-yl)acrylate 
In the title compound, C12H8N2O6, the 1,3-benzodioxole ring system is essentially planar [maximum deviation = 0.036 (2) Å] and the nitro group is oriented at a dihedral angle of 15.4 (1)° with respect to its mean plane. In the crystal, moleucles are linked into C(8) [101] chains by C—H⋯O hydrogen bonds, and weak aromatic π–π stacking [centroid–centroid distance = 3.887 (1) Å] also occurs.
doi:10.1107/S1600536812043164
PMCID: PMC3515275  PMID: 23284495
24.  2-[Hy­droxy(2-meth­oxy­phenyl)methyl]acrylonitrile 
In the title compound, C11H11NO2, the mean planes formed by the benzene ring and the C and N atoms of the acryl group are almost orthogonal to each other, with a dihedral angle of 85.7 (1)°. During the structure analysis, it was observed that the unit cell contains large accessible voids, with a volume of 186.9 Å3, which may host disordered solvent mol­ecules. This affects the diffraction pattern, mostly at low scattering angles. Density identified in these solvent-accessible areas was calculated and corrected for using the SQUEEZE routine in PLATON [Spek (2009 ▶), Acta Cryst. D65, 148–155]. Despite the presence of the hy­droxy group in the mol­ecule, no classical or nonclassical hydrogen bonds are observed in the structure. This may reflect the fact that the O—H group points towards the solvent-accessible void.
doi:10.1107/S1600536812031728
PMCID: PMC3414923  PMID: 22904910
25.  2-(2-Nitro­phen­yl)-1,3-benzothia­zole 
In the title compound, C13H8N2O2S, the essentially planar benzothia­zole system [maximum deviation = −0.012 (1) Å for the S atom] is oriented at a dihedral angle of 48.3 (1)° with respect to the benzene ring. The nitro group is substanti­ally twisted from the plane of its attached benzene ring [dihedral angle = 52.0 (1)°]. The crystal packing features C—H⋯O hydrogen bonds, which generate C(6) helical chains propagating along [010]. Weak C—H⋯π inter­actions also occur in the crystal.
doi:10.1107/S1600536812029844
PMCID: PMC3414295  PMID: 22904828

Results 1-25 (74)