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Methyl 11-hy-droxy-9-[1-(4-meth-oxy-phen-yl)-4-oxo-3-phenyl-azetidin-2-yl]-18-oxo-10-oxa-2-aza-penta-cyclo-[9.7.0.0(1,8).0(2,6).0(12,17)]octa-deca-12(17),13,15-triene-8-carboxyl-ate.

ABSTRACT: In the title compound, C34H32N2O7, the furan ring adopts a twist conformation and both the pyrrolidine rings adopt envelope conformations with O and C as flap atoms. The ?-lactam ring makes a dihedral angles of 80.20?(10)° with the furan ring, of 75.55?(10)° with the pyrrolidine ring, of 12.26?(10)° with the meth-oxy-phenyl ring and of 73.77?(13)° with the phenyl ring. The O atom attached to the ?-lactam ring deviates by 0.0385?(13)?Å from the ring plane. The mol-ecular conformation is stabilized by intra-molecular O-H?N and C-H?O hydrogen bonds. The packing of the crystal is stabilized by inter-molecular C-H?O hydrogen bonds, which form a chain running along the b axis.

SUBMITTER: Suhitha S

PROVIDER: S-EPMC3588541 | biostudies-literature | 2013 Mar

REPOSITORIES: biostudies-literature

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Methyl 11-hy-droxy-9-[1-(4-meth-oxy-phen-yl)-4-oxo-3-phenyl-azetidin-2-yl]-18-oxo-10-oxa-2-aza-penta-cyclo-[9.7.0.0(1,8).0(2,6).0(12,17)]octa-deca-12(17),13,15-triene-8-carboxyl-ate.

Suhitha Sivasubramanian S Srinivasan Thothadri T Rajesh Raju R Raghunathan Raghavachary R Velmurugan Devadasan D

Acta crystallographica. Section E, Structure reports online 20130223 Pt 3

In the title compound, C34H32N2O7, the furan ring adopts a twist conformation and both the pyrrolidine rings adopt envelope conformations with O and C as flap atoms. The β-lactam ring makes a dihedral angles of 80.20 (10)° with the furan ring, of 75.55 (10)° with the pyrrolidine ring, of 12.26 (10)° with the meth-oxy-phenyl ring and of 73.77 (13)° with the phenyl ring. The O atom attached to the β-lactam ring deviates by 0.0385 (13) Å from the ring plane. The mol-ecular conformation is stabilize ...[more]

PMID: 23476608

Similar Datasets

Methyl 11-hy-droxy-9-[1-(4-meth-oxy-phen-yl)-4-oxo-3-phen-oxy-azetidin-2-yl]-18-oxo-10-oxa-2-aza-penta-cyclo-[9.7.0.0(1,8).0(2,6).0(12,17)]octa-deca-12(17),13,15-triene-8-carboxyl-ate.

Project description:In the title compound, C(34)H(32)N(2)O(8), one of the pyrrolidine rings in the pyrrolizidine ring system adopts a twist conformation, whereas the other ring adopts an envelope conformation (C atom as flap). The five-membered ring in the indene ring system and the fused furan ring also adopt envelope conformations (C and O atoms as flaps, respectively). The β-lactam ring makes dihedral angles of 23.41 (2) and 25.98 (2)°, respectively, with the attached meth-oxy-phenyl and phen-oxy rings. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯N hydrogen bond, generating an S(5) motif. In the crystal, mol-ecules are linked into C(12) chains running along the a axis by C-H⋯O hydrogen bonds. The structure is further consolidated by weak inter-molecular C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.7987 (14) Å].

| S-EPMC3393998 | biostudies-literature

11-Hy-droxy-9-[1-(4-methyl-phen-yl)-4-oxo-3-phenyl-azetidin-2-yl]-18-oxo-10-oxa-2-aza-penta-cyclo-[9.7.0.0(1,8).0(2,6).0(12,17)]octa-deca-12,14,16-triene-8-carbonitrile.

Project description:In the title compound, C33H29N3O5, the four-membered ring of the ?-lactam fragment is essentially planar (r.m.s. deviation = 0.0122?Å), with the carbonyl O atom displaced from this ring by 0.856?(9)?Å. The mean planes of the meth-oxy-phenyl and phenyl rings are inclined at dihedral angles 85.10?(7) and 21.56?(14)°, respectively, with respect to the mean plane of the four-membered ring. The pyrrolidine rings adopt envelope conformations with C atoms lying 0.535?(4) and 0.519?(4)?Å out of the planes formed by the remaining ring atoms. The furan ring also adopts an envelope conformation with a C atom 0.560?(3)?Å out of the plane formed by the remaining ring atoms. The nine-membered indene ring is almost planar (r.m.s. deviation = 0.0240?Å), with the carbonyl O atom displaced by 0.145?(3)?Å from this ring. The mol-ecular structure is stabilized by a strong intra-molecular O-H?N hydrogen bond and the crystal structure is consolidated by C-H?O hydrogen bonds.

| S-EPMC3588836 | biostudies-other

11-[1-(4-Meth-oxy-phen-yl)-4-oxo-3-phen-oxy-azetidin-2-yl]-14-methyl-12-oxa-8,14-diaza-tetra-cyclo-[8.3.3.0(1,10).0(2,7)]hexa-deca-2(7),3,5-triene-9,13-dione.

Project description:In the title compound, C(30)H(27)N(3)O(6), the furan and pyrrolidine rings adopt envelope conformations (with C and N atoms as the flaps, respectively). The piperidine ring is in a distorted boat conformation. The β-lactam ring is planar [maximum deviation = 0.0044 (16) Å] and forms dihedral angles of 30.61 (9) and 85.51 (9)°, respectively, with the attached meth-oxy-phenyl and phen-oxy rings. The crystal packing is stabilized by N-H⋯O and C-H⋯O inter-actions forming R(2) (2)(8), R(2) (2)(20) and R(2) (2)(14) ring motifs. The crystal structure is further consolidated by weak C-H⋯π inter-actions.

| S-EPMC3393999 | biostudies-literature

2,9-Diiodo-hexa-cyclo-[9.3.1.1(2,6).1(4,8).1(9,13).0(1,8)]octa-deca-ne.

Project description:The title compound, C(18)H(24)I(2), has an adamantanoid structure with tetra-hedral cages having four C atoms lying on the same plane [(I-)C-C-C-C(-I) torsion angle = 0°]. The plane is extended by the two I atoms, each having a deviation of 1.0?(6)?Å [C-C-C-I torsion angle = 178.9?(4)°]. The central C-C bond connecting the two quaternary carbons seems enlarged [1.593?(9)?Å] in comparison to the corresponding bond in [2]diadamantane [1.554?(3)?Å]. This is attributed to the presence of the electronegative I atoms, which affect inductively the C atoms of the four-C-atom plane, making the central C-C bond weaker.

| S-EPMC3414276 | biostudies-literature

Crystal structures and conformations of two Diels-Alder adduct derivatives: 1,8-bis-(thio-phen-2-yl)-14-oxa-tetra-cyclo-[6.5.1.0(2,7).0(9,13)]tetra-deca-2(7),3,5-trien-10-one and 1,8-diphenyl-14-oxa-tetra-cyclo[6.5.1.0(2,7).0(9,13)] tetra-deca-2,4,6-trien-10-one.

Project description:The title compounds, C21H16O2S2 (I) and C25H20O2 (II), are products of a tandem 'pincer' Diels-Alder reaction consisting of [2 + 2] cyclo-additions between benzo[c]furan and cyclo-penta-none. Each comprises a fused tetra-cyclic ring system containing two five-membered rings (in envelope conformations with the O atom as the flap) and six-membered rings (in boat conformations). In addition, two thio-phene rings in (I) and two phenyl rings in (II) are attached to the tetra-cyclic ring system. The cyclo-penta-none ring adopts a twisted conformation in (I) and an envelope conformation in (II). In (I), the thio-phene rings are positionally disordered over two sets of sites, with occupancy ratios of 0.901?(2):0.099?(2) and 0.666?(2):0.334?(2). In (II), the oxygen atom of the cyclo-penta-none ring is rotationally disordered over two sites with an occupancy ratio of 0.579?(4):0.421?(4). The mol-ecular structure of (I) is stabilized by an intra-molecular C-H?O hydrogen bond, which generates an S(7) ring motif. In the crystal, the mol-ecules are linked via weak C-H?O hydrogen bonds, which generate R (2) 2(16) ring motifs in (I) and C(8) chains in (II). In both structures, the crystal packing also features C-H?? inter-actions. The crystal studied of compound (I) was twinned by non-merohedry. The twin component is related by the twin law [-1 0 0 -0.101 1 -0.484 0 0 -1] operated by a twofold rotation axis parallel to the b axis. The structure of (I) was refined with a twin scale factor of 0.275?(2).

| S-EPMC4384542 | biostudies-literature

Crystal structure of methyl 2-(2H-1,3-benzodioxol-5-yl)-7,9-di-bromo-8-oxo-1-oxa-spiro-[4.5]deca-2,6,9-triene-3-car-boxyl-ate.

Project description:The title compound, C18H12Br2O6, was synthesized from Morita-Baylis-Hillman adducts. It incorporates the bromin-ated spiro-hexa-dienone moiety typically exhibited by compounds of this class that exhibit biological activity. Both the brominated cyclo-hexa-dienone and the central five-membered rings are nearly planar (r.m.s. deviations of 0.044 and 0.016?Å, respectively), being almost perpendicularly oriented [inter-planar angle = 89.47?(5)°]. With respect to the central five-membered ring, the brominated cyclo-hexa-dienone ring, the benzodioxol ring and the carboxyl-ate fragment make C-O-C-C, O-C-C-C and C-C-C-O dihedral angles of -122.11?(8), -27.20?(11) and -8.40?(12)°, respectively. An intra-molecular C-H?O hydrogen bond occurs. In the crystal, mol-ecules are linked by non-classical C-H?O and C-H?Br hydrogen bonds resulting in a molecular packing in which the brominated rings are in a head-to-head orientation, forming well marked planes parallel to the b axis.

| S-EPMC4257376 | biostudies-literature

2,5,11,14-Tetra-oxa-8-aza-dispiro-[13.4.0]nona-deca-15,17,19-triene.

Project description:The title compound, C(14)H(21)NO(4), has been synthesized from o-dihydroxy-benzene by a three-step reaction. There are two chemically equal but crystallographically independent mol-ecules in the asymmetric unit. The crystal packing is governed by C-H?O hydrogen bonds and C-H?? inter-actions, forming an infinite network.

| S-EPMC2979120 | biostudies-literature

Methyl 9-hy-droxy-15-methyl-2-oxo-11-(pyren-1-yl)-10-oxa-15-aza-tetra-cyclo-[7.6.0.0(1,12).0(3,8)]penta-deca-3(8),4,6-triene-12-carboxyl-ate.

Project description:In the title compound, C32H25NO5, the furan and pyrrole rings each adopt an envelope conformation, the respective flap atoms being the C atom bearing the pyrene substituent and the CH2 atom adjacent to the N atom. The mol-ecular conformation is stabilized by an intra-molecular O-H?N hydrogen bond. In the crystal, C-H?O contacts link the mol-ecules, forming a two-dimensional network parallel to (001).

| S-EPMC3790429 | biostudies-other

Crystal structure of 14-methyl-11-(3-methyl-phen-yl)-12-oxa-8,14-di-aza-tetra-cyclo-[8.3.3.0(1,10).0(2,7)]hexa-deca-2(7),3,5-triene-9,13-dione.

Project description:In the title compound, C21H20N2O3, the lactone ring adopts an envelope conformation with the quaternary C atom bonded to two other C atoms as the flap. The fused pyrrolidine ring adopts a twisted conformation about the Cq-N (q = quaternary) bond. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R 2 (2)(8) loops. The dimers are linked into [110] chains by pairs of C-H⋯O inter-actions, which generate R 2 (2)(14) loops.

| S-EPMC4459358 | biostudies-literature

Ethyl 27-oxo-15-oxa-2,20-diaza-hexa-cyclo-[18.6.1.0(1,8).0(2,6).0(9,14).0(21,26)]hepta-cosa-9,11,13,21,23,25-hexa-ene-7-carboxyl-ate.

Project description:In the title compound, C27H30N2O4, the pyrrolidine ring adopts a twisted conformation. The indoline ring system is almost perpendicular to the mean plane of the pyrrolidine ring, making a dihedral angle of 81.7?(8)°. In the crystal, mol-ecules are linked into centrosymmetric dimers with graph-set motif R2(2)(16) via pairs of C-H?O hydrogen bonds. The terminal ethyl group of the ester group is disordered over two sets of sites, with a site-occupancy ratio of 0.587?(11):0.413?(11).

| S-EPMC3588369 | biostudies-literature

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