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Ethyl 3-(4-chloro-benzo-yl)-1-(4-chloro-benz-yl)-4-(4-chloro-phen-yl)-2,2-dioxo-3,4,6,7,8,8a-hexa-hydro-1H-pyrrolo-[2,1-c][1,4]thia-zine-1-carboxyl-ate.

ABSTRACT: In the title compound, C30H28Cl3NO5S, the pyrrolidine ring adopts an envelope conformation (with the N atom as the flap) and the thia-zine ring is in a distorted chair conformation. The mol-ecular structure shows three intra-molecular C-H?O inter-actions leading to self-associated ring S(6) and two S(7) motifs. In the crystal, the molecules are linked by C-H?O and C-H?Cl inter-actions. Two R 2 (2)(10) and one R 2 (2)(16) centrosymmetrically related ring motifs are observed in the unit cell and they are connected through C(6) and C(11) chain motifs extending along the b and c axes, respectively.

SUBMITTER: Chitradevi A

PROVIDER: S-EPMC3648240 | biostudies-literature | 2013 May

REPOSITORIES: biostudies-literature

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Ethyl 3-(4-chloro-benzo-yl)-1-(4-chloro-benz-yl)-4-(4-chloro-phen-yl)-2,2-dioxo-3,4,6,7,8,8a-hexa-hydro-1H-pyrrolo-[2,1-c][1,4]thia-zine-1-carboxyl-ate.

Chitradevi A A Athimoolam S S Bahadur S Asath SA Indumathi S S Perumal S S

Acta crystallographica. Section E, Structure reports online 20130413 Pt 5

In the title compound, C30H28Cl3NO5S, the pyrrolidine ring adopts an envelope conformation (with the N atom as the flap) and the thia-zine ring is in a distorted chair conformation. The mol-ecular structure shows three intra-molecular C-H⋯O inter-actions leading to self-associated ring S(6) and two S(7) motifs. In the crystal, the molecules are linked by C-H⋯O and C-H⋯Cl inter-actions. Two R 2 (2)(10) and one R 2 (2)(16) centrosymmetrically related ring motifs are observed in the unit cell and t ...[more]

PMID: 23723860

Similar Datasets

Isomorphous diethyl 1-(4-chloro-benz-yl)-4-(4-chloro-phen-yl)-2,2-dioxo-3,4,6,7,8,8a-hexa-hydro-1<i>H</i>-pyrrolo-[2,1-<i>c</i>][1,4]thia-zine-1,3-di-carboxyl-ate and its 1-(4-methyl-benz-yl)-4-(4-methyl-phen-yl)-substituted analogue obeying the chloro-methyl exchange rule.

Project description:Accurate studies on the effect of substituents on the crystal packing are essential for understanding the inter-molecular inter-actions and thus paving the way to crystal structure prediction. The crystal structures of diethyl 1-(4-chloro-benz-yl)-4-(4-chloro-phen-yl)-2,2-dioxo-3,4,6,7,8,8a-hexa-hydro-1H-pyrrolo-[2,1-c][1,4]thiazine-1,3-di-carboxyl-ate, C26H29Cl2NO6S, (I), and its isomorphous pair diethyl 1-(4-methyl-benz-yl)-4-(4-methyl-phen-yl)-2,2-dioxo-3,4,6,7,8,8a-hexa-hydro-1H-pyrrolo-[2,1-c][1,4]thia-zine-1,3-di-carboxyl-ate, C28H35NO6S, (II), are described. The mol-ecular aggregation patterns appear to be strikingly similar despite changes in the substituents, with a Cl atom in (I) being replaced by a methyl group in (II). Inspite of the chemical modifications, the structures of (I) and (I) are isomorphous, isostructural and found to obey the chlorine-methyl exchange rule. Both the structures feature C-H?O hydrogen bonding. However, a distinguishing feature between (I) and (II) is observed in the conformation of the pyrrole rings where the twist occurs on different C-N bonds. Hirshfeld analysis of both structures is presented and discussed.

| S-EPMC6127705 | biostudies-literature

Diethyl 1-benzyl-2,2-dioxo-4-phenyl-3,4,6,7,8,8a-hexa-hydro-1H-pyrrolo-[2,1-c][1,4]thia-zine-1,3-dicarboxyl-ate.

Project description:In the title compound, C(26)H(31)NO(6)S, the five-membered pyrrolidine ring adopts an envelope conformation and the six-membered thia-zine ring is in a distorted chair conformation. The crystal packing is stabilized through an inter-molecular C-H?O inter-action, generating inversion-related R(2) (2)(10) ring motifs.

| S-EPMC3200855 | biostudies-other

Methyl 5-chloro-4-hy-droxy-2,2-dioxo-1H-2?6,1-benzo-thia-zine-3-carboxyl-ate: structure and Hirshfeld surface analysis.

Project description:The title compound, C10H8ClNO5S, which has potential analgesic activity, crystallizes in space group P21/n. The benzo-thia-zine ring system adopts an inter-mediate form between sofa and twist-boat conformations. The coplanarity of the ester substituent to the bicyclic fragment is stabilized by an O-H?O intra-molecular hydrogen bond. In the crystal, hydrogen bonds of type N-H?O(SO2) link the mol-ecules into zigzag chains extending along the b-axis direction. Neighbouring chains are linked by both O-H?Cl and C-H?Cl inter-actions. A Hirshfeld surface analysis was used to compare different types of inter-molecular inter-actions, giving contributions of O?H/H?O = 42.0%, C?H/H?C = 17.3%, Cl?H/H?Cl = 14.2%, H?H = 11.1%.

| S-EPMC7534242 | biostudies-literature

Ethyl 6-amino-8-(4-chloro-phen-yl)-9-nitro-2,3,4,8-tetra-hydro-pyrido[2,1-b][1,3]thia-zine-7-carboxyl-ate.

Project description:In the structure of the title compound, C(17)H(18)ClN(3)O(4)S, the thia-zinane ring displays a twist-boat conformation. The 1,4-dihydro-pyridine ring is approximately perpendicular to the benzene ring [dihedral angle = 88.3?(1)°]. The mol-ecular conformation is stabilized by an intra-molecular N-H?O hydrogen bond. In the crystal, mol-ecules are linked by N-H?O inter-actions into a C(8) chain along [100].

| S-EPMC3200856 | biostudies-other

3-[(4-Amino-5-chloro-2-ethoxy-benz-amido)meth-yl]pyrrolo[2,1-c][1,4]oxazin-5-ium chloride monohydrate.

Project description:The title compound, C(17)H(25)ClN(3)O(3) (+)·Cl(-)·H(2)O, is a monohydrated hydro-chloride salt of a new derivative of mosapride, which is a pharmaceutical compound possessing gastrointestinal pro-kinetic activity. The chloride anion accepts hydrogen bonds from the NH group of the pyrrolooxazine fused-ring system and from the amine group, and the water mol-ecules form hydrogen bonds that bridge between the chloride anion and the C=O bond of the amide.

| S-EPMC2967935 | biostudies-literature

2,5-Bis[(3-chloro-benz-yl)sulfan-yl]-1,3,4-thia-diazole.

Project description:The complete mol-ecule of the title compound, C(16)H(12)Cl(2)N(2)S(3), is generated by crystallographic twofold symmetry, with the S atom of the thiadiazole ring lying on the rotation axis. The dihedral angle between the mean planes of the 1,3,4-thia-diazole and benzene rings is 87.19 (7)°. In the crystal, mol-ecules are linked by C-H⋯N inter-actions and short S⋯S contacts [3.3389 (9) Å] occur.

| S-EPMC3379226 | biostudies-literature

10-Ethynyl-2,3,6,6a,9,10-hexa-hydro-1H-6,9-methano-pyrrolo[2,1-i][2,1]benzo-thia-zol-10-ol 5,5-dioxide.

Project description:In the title compound, C(13)H(15)NO(3)S, the sole classical hydrogen-bond donor is involved in an intra-molecular O-H?N hydrogen bond. In the crystal structure, pairs of mol-ecules related by inversion centres are linked by pairs of weak inter-molecular C-H?O inter-actions; these centrosymmetric pairs are, in turn, linked further by weak inter-molecular C-H?O inter-actions, forming two-dimensional sheets oriented parallel to (101).

| S-EPMC2971063 | biostudies-literature

Dimethyl 3-(cyclo-propyl-carbon-yl)pyrrolo-[2,1-a]isoquinoline-1,2-dicarboxyl-ate.

Project description:In the mol-ecular structure of the title compound, C(20)H(17)NO(5), two intra-molecular C-H?O hydrogen bond generate six- and seven-membered ring motifs. The dihedral angles between the almost planar 13-atom triple-fused-ring system (r.m.s. deviation = 0.003?Å) and the planes of the two meth-oxy-carbonyl substituents are 61.7?(2) and 33.01?(10)°.

| S-EPMC3344550 | biostudies-literature

6-(3-Chloro-phen-yl)imidazo[2,1-b][1,3,4]thia-diazole.

Project description:In the title compound, C10H8ClN3S, the dihedral angle between the mean planes of the benzene and imidazo[2,1-b][1,3,4]thia-diazole rings is 6.0?(9)°. In the crystal, mol-ecules are assembled by the formation of centrosymmetric dimers by ?-stacking of the thia-diazole and benzene rings of neighboring mol-ecules [centroid-centroid distance = 3.6938?(11)?Å] along [010].

| S-EPMC3588322 | biostudies-literature

Crystal structures of three 6-aryl-2-(4-chloro-benz-yl)-5-[(1H-indol-3-yl)meth-yl]imidazo[2,1-b][1,3,4]thia-diazo-les.

Project description:Three title compounds, namely, 2-(4-chloro-benz-yl)-5-[(1H-indol-3-yl)meth-yl]-6-phenyl-imidazo[2,1-b][1,3,4]thia-diazole, C26H19ClN4S, (I), 2-(4-chloro-benz-yl)-6-(4-fluoro-phen-yl)-5-[(1H-indol-3-yl)meth-yl]imidazo[2,1-b][1,3,4]thia-diazole, C26H18ClFN4S, (II), and 6-(4-bromo-phen-yl)-2-(4-chloro-benz-yl)-5-[(1H-indol-3-yl)meth-yl]imidazo[2,1-b][1,3,4]thia-diazole, C26H18BrClN4S, (III), have been prepared using a reductive condensation of indole with the corresponding 6-aryl-2-(4-chloro-benz-yl)imidazo[2,1-b][1,3,4]thia-diazole-5-carbaldehydes (aryl = phenyl, 4-fluoro-phenyl or 4-bromo-phen-yl), and their crystal structures have been determined. The asymmetric unit of compound (I) consists of two independent mol-ecules and one of the mol-ecules exhibits disorder of the 4-chloro-benzyl substituent with occupancies 0.6289?(17) and 0.3711?(17). Each type of mol-ecule forms a C(8) chain motif built from N-H?N hydrogen bonds, which for the fully ordered mol-ecule is reinforced by C-H?? inter-actions. In compound (II), the chloro-benzyl unit is again disordered, with occupancies 0.822?(6) and 0.178?(6), and the mol-ecules form C(8) chains similar to those in (I), reinforced by C-H?? inter-actions involving only the major disorder component. The chloro-benzyl unit in compound (III) is also disordered with occupancies of 0.839?(5) and 0.161?(5). The mol-ecules are linked by a combination of one N-H?N hydrogen bond and four C-H?? inter-actions, forming a three-dimensional framework.

| S-EPMC6944076 | biostudies-literature

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