Crystal structure of ethyl (2S,2'R)-1'-benzyl-3-oxo-3H-di-spiro-[1-benzo-thio-phene-2,3'-pyrrolidine-2',11''-indeno[1,2-b]quinoxaline]-4'-carboxyl-ate.
ABSTRACT: In the title compound, C35H27N3O3S, the spiro-linked five-membered rings both adopt twisted conformations. The pyrrolidine ring makes dihedral angles of 80.5?(1) and 77.4?(9)° with the benzo-thio-phene ring system and the quinoxaline ring system, respectively. The S atom and C=O unit of the benzo-thio-phene ring system are disordered over two opposite orientations in a 0.768?(4):0.232?(4) ratio. The atoms of the ethyl side chain are disordered over two sets of sites in a 0.680?(16):0.320?(16) ratio. In the crystal, mol-ecules are linked by C-H?O, C-H?N and ?-? inter-actions [shortest centroid-centroid distance = 3.4145?(19)?Å], resulting in a three-dimensional network.
Project description:In the title compound, C(14)H(13)N(3)OS(2), the thio-phene ring is disordered over two orientations by ca 180° about the C-C bond axis linking the ring to the rest of the mol-ecule, with a site-occupancy ratio of 0.651?(5):0.349?(5). The central 1,3,4-oxadiazole-2(3H)-thione ring forms dihedral angles of 9.2?(5), 4.6?(11) and 47.70?(7)° with the major and minor parts of the disordered thio-phene ring and the terminal phenyl ring, respectively. In the crystal, no significant inter-molecular hydrogen bonds are observed. The crystal packing is stabilized by ?-? inter-actions [centroid-centroid distance = 3.589?(2)?Å].
Project description:The title compound, C(16)H(10)N(2)S, is almost planar (r.m.s. deviation for all non-H atoms = 0.080?Å). The dihedral angle between the three fused-ring system and the phenyl ring is 9.26?(3)°. The S atom and the opposite C atom of the thio-phene ring are mutually disordered with an occupancy ratio of 0.7706?(19):0.2294?(19).
Project description:In the title mol-ecule, C(16)H(16)O(4)S, the enone fragment, thio-phene ring and benzene ring are individually essentially planar. The thio-phene ring is disordered over two sites, corresponding to a rotation of approximately 180° about the single C-C bond to which it is attached. The approximate ratio of occupancies for the major and minor components is 0.872?(2):0.128?(2). The major component of the thio-phene ring and the benzene ring are twisted from each other by 13.92?(19)°. An intra-molecular C-H?O hydrogen bond generates an S(5)S(5) ring motif. The crystal structure is stabilized by inter-molecular C-H?O hydrogen-bonding inter-actions. In addition, a ?-? stacking inter-action, with a centroid-centroid distance of 3.852?(2)?Å, and short S?O [2.9378?(12)?Å] and O?O [2.5811?(16)?Å] contacts are observed.
Project description:In the title compound, C(22)H(19)NOS(2), the thio-phene rings form angles of 69.74?(18) and 65.56?(16)° with the benzene ring. The piperidone ring adopts a half-chair conformation due to the presence of the conjugated ketone systems. Both thio-phene rings are disordered over two orientations [occupancies of 0.758?(2)/0.242?(2) and 0.588?(2)/0.412?(2)] at 180° from one another. In the crystal, weak inter-molecular C-H?O hydrogen bonds, C-H?? and aromatic ?-? stacking inter-actions [shortest centroid-centroid separation = 3.865?(3)?Å] help to stabilize the packing.
Project description:The title compound, C(26)H(26)N(2)O(2)S, was prepared by the reaction of thio-phene-2,5-dicarboxylic acid and 2-amino-4-tert-butyl-phenol. One of the tert-butyl groups is disordered over two conformations, with occupancies of 0.539 (1) and 0.461 (2). The two 1,3-benzoxazole rings are almost planar, with dihedral angles of 0.83 (18) and 1.64 (17)° between the five- and six-membered rings. The thio-phene ring makes dihedral angles of 21.54 (19) and 4.49 (18)° with the planes of the five-membered oxazole rings. The crystal packing is controlled by π-π stacking inter-actions involving the thio-phene and benzene rings, with a centroid-centroid distance of 3.748 (2) Å.
Project description:In the title compound, C23H20N2O4S2, the central pyrrolidine ring adopts an envelope conformation with the spiro C atom, shared with the benzo-thio-phene ring system, as the flap. The thia-zole ring has a twisted conformation on the S-C bond, where the C atom is that closest to methine C atom. The mean planes of the benzo-thio-phene and indoline ring systems are inclined to the mean plane of the central pyrrolidine ring by 82.75?(8) and 80.03?(8)°, respectively, and to each other by 61.49?(6)°. In the crystal, mol-ecules are linked via pairs of N-H?O hydrogen bonds, forming inversion dimers with an R 2 (2)(8) ring motif. The dimers are linked via C-H?O and C-H?N hydrogen bonds, forming a three-dimensional structure. The eth-oxy-carbonyl group is disordered over two orientations, with an occupancy ratio of 0.717?(12):0.283?(12).
Project description:In the title mol-ecule, C24H23N3O3S2, the benzo-thia-diazole ring system is essentially planar, with an r.m.s. deviation of 0.020?(8)?Å. The thio-phene and hy-droxy-substitiuted rings form dihedral angles of 23.43?(9) and 35.45?(9)°, respectively, with the benzo-thia-diazole ring system. An intra-molecular O-H?N hydrogen bond is observed. In the crystal, weak C-H?O hydrogen bonds and ?-? stacking inter-actions [centroid-centroid distance = 3.880?(3)?Å] link mol-ecules into chains along . In addition, there are short S?S contacts [3.532?(3)?Å] which link these chains, forming a two-dimensional network parallel to (010).
Project description:In the cation of the title hydrated salt, C19H21N2O2S2 (+)·I(-)·H2O, the benzo-thia-zolium ring system is approximately planar [maximum deviation = 0.0251?(15)?Å], and it makes a small dihedral angle of 1.16?(18)° with the plane of the thio-phene ring. In the crystal, the cations, anions and crystalline water mol-ecules are linked by classical O-H?O, O-H?I and weak C-H?O hydrogn bonds, forming a three-dimensional supra-molecular network. ?-? stacking is observed between parallel thia-zole rings of adjacent cations [centroid-centroid distance = 3.5945?(16)?Å].
Project description:The title compound, C19H17N3O3S (I), was prepared by a [3 + 2]cyclo-addition azide condensation reaction using sodium azide and l-proline as a Lewis base catalyst. N-Methyl-ation of compound (I) using CH3I gave compound (II), C20H19N3O3S. The benzo-thio-phene ring systems in (I) and (II) are almost planar, with r.m.s deviations from the mean plane = 0.0205?(14) in (I) and 0.016?(2)?Å in (II). In (I) and (II), the triazole rings make dihedral angles of 32.68?(5) and 10.43?(8)°, respectively, with the mean planes of the benzo-thio-phene ring systems. The trimeth-oxy phenyl rings make dihedral angles with the benzo-thio-phene rings of 38.48?(4) in (I) and 60.43?(5)° in (II). In the crystal of (I), the mol-ecules are linked into chains by N-H?O hydrogen bonds with R (2) 1(5) ring motifs. After the N-methyl-ation of structure (I), no hydrogen-bonding inter-actions were observed for structure (II). The crystal structure of (II) has a minor component of disorder that corresponds to a 180° flip of the benzo-thio-phene ring system [occupancy ratio 0.9363?(14):0.0637?(14)].
Project description:In the title compound, C16H13Cl2N3O3S2, the thio-phene ring is disordered in a 0.762?(3):0.238?(3) ratio by an approximate 180° rotation of the ring around the S-C bond linking the ring to the sulfonyl unit. The di-chloro-benzene group is also disordered over two sets of sites with the same occupancy ratio. The mol-ecular conformation is stabilized by intra-molecular C-H?Cl and C-H?N hydrogen bonds, forming rings with graph-set notation S(5). In the crystal, pairs of mol-ecules are linked by N-H?O and C-H?O hydrogen bonds, forming inversion dimers with graph-set notation R22(8) and R12(11), which are connected by C-H?O hydrogen-bonding inter-actions into ribbons parallel to (100). The ribbons are further connected into a three-dimensional network by C-H?? inter-actions and ?-? stacking inter-actions between benzene and thio-phene rings, with centroid-to-centroid distances of 3.865?(2), 3.867?(7) and 3.853?(2)?Å. Hirshfeld surface analysis has been used to confirm and qu-antify the supra-molecular inter-actions.