Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Mol-ecular and crystal structure of methyl 4-methyl-2,2-dioxo-1H-2?⁶,1-benzo-thia-zine-3-carboxyl-ate.

ABSTRACT: The title compound, C₁₁H₁₁NO₄S, possesses weak analgesic properties and is a source compound for the synthesis of highly active analgesic and anti-inflammatory compounds. The benzo-thia-zine ring adopts a conformation intermediate between twist-boat and sofa. The ester substituent is turned towards the endocyclic double bond because of steric repulsion. In the crystal, the mol-ecules form columns along the [001] direction, bound by N-H?O hydrogen bonds and stacking inter-actions.

SUBMITTER: Shishkina S

PROVIDER: S-EPMC6127716 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Mol-ecular and crystal structure of methyl 4-methyl-2,2-dioxo-1H-2λ6,1-benzo-thia-zine-3-carboxyl-ate.

Shishkina Svitlana S Ukrainets Igor I Hamza Ganna G Grinevich Lina L

Acta crystallographica. Section E, Crystallographic communications 20180821 Pt 9

The title compound, C11H11NO4S, possesses weak analgesic properties and is a source compound for the synthesis of highly active analgesic and anti-inflammatory compounds. The benzo-thia-zine ring adopts a conformation intermediate between twist-boat and sofa. The ester substituent is turned towards the endocyclic double bond because of steric repulsion. In the crystal, the mol-ecules form columns along the [001] direction, bound by N-H⋯O hydrogen bonds and stacki ...[more]

PMID: 30225121

Similar Datasets

Methyl 1-allyl-4-hy-droxy-2,2-dioxo-1H-2?(6),1-benzo-thia-zine-3-carboxyl-ate.

Project description:There are two independent mol-ecules in the asymmetric unit of the title compound, C13H13NO5S, in both of which the ester substituent is nearly coplanar [C-C-C-O torsion angles = 2.7?(7) and -0.8?(7)°] with the planar fragment of the bicycle due to the formation of a strong O-H?O intra-molecular hydrogen bond. The vinyl group at the ring N atom is approximately orthogonal to the heterocyclic mean plane [C-N-C-C torsion angles = 103.1?(6) and 98.2?(5)°]. The refinement was performed on a two-component, non-merohedrally twinned crystal [population ratio = 0.483?(3):0.517?(3).

| S-EPMC3884348 | biostudies-literature

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

Methyl 2-ethyl-4-hydr-oxy-2H-1,2-benzo-thia-zine-3-carboxyl-ate 1,1-dioxide.

Project description:In the title compound, C(12)H(13)NO(5)S, the thia-zine ring adopts a half chair conformation and an intra-molecular O-H?O hydrogen bond generates an S(6) ring. In the crystal, the mol-ecules are linked by C-H?O inter-actions, leading to zigzag chains along the b axis.

| S-EPMC2979064 | biostudies-literature

Crystal structure of methyl 1-allyl-4-methyl-1H-benzo[c][1,2]thia-zine-3-carboxyl-ate 2,2-dioxide.

Project description:In the title compound, C14H15NO4S, the di-hydro-thia-zine ring adopts a distorted sofa conformation with the S atom displaced from the mean plane through the N and C ring atoms by 0.767 (1) Å. The allyl substituent (C-C=C) is inclined to this mean plane by 78.5 (7)° and the acetate group [C(=O)-O-C] by 66.5 (3)°. In the crystal, mol-ecules are linked by C-H⋯π inter-actions forming chains propagating along the a-axis direction.

| S-EPMC5095836 | biostudies-literature

Crystal structure of 2-(4-methyl-phen-yl)-4H-1,3-benzo-thia-zine.

Project description:In the title compound, C15H13NS, the thia-zine ring adopts a boat conformation. The dihedral angle between the planes of the benzene ring of the benzo-thia-zine unit and the tolyl ring is 19.52?(9)°. In the crystal, mol-ecules are linked by weak C-H?? inter-actions into a tape structure along the b-axis direction.

| S-EPMC4384615 | biostudies-literature

Methyl 4-hy-droxy-2-isopropyl-1,1-dioxo-2H-1,2-benzothia-zine-3-carboxyl-ate.

Project description:In the crystal structure of the title mol-ecule, C(13)H(15)NO(5)S, the S and N atoms of the thia-zine ring exihibit the maximum deviations from the least-squares plane of 0.3008?(6) and 0.3280?(7)?Å, respectively. The ring therefore adopts a half chair conformation. The thia-zine ring is twisted by an angle of 13.29?(7)° with respect to the aromatic ring. The isopropyl substituent is oriented at a dihedral angle of 53.2?(12)° with respect to the thia-zine ring. An intra-molecular O-H?O hydrogen bond occurs. Inter-molecular hydrogen bonding is observed in the crystal structure.

| S-EPMC3152111 | biostudies-literature

Methyl 2-butyl-4-hy-droxy-1,1-dioxo-2H-1,2-benzothia-zine-3-carboxyl-ate.

Project description:In the title compound, C(14)H(17)NO(5)S, the thia-zine ring adopts a half-chair conformation. The mol-ecule exhibits an intra-molecular O-H?O hydrogen bond, which forms a six-membered S(6) ring motif. The planes of the benzene and thia-zine rings are inclined at a dihedral angle of 15.30?(12)°.

| S-EPMC3379260 | biostudies-literature

6-Bromo-4-(2-cyclo-hexyl-idenehydrazin-1-yl-idene)-1-methyl-2,2-dioxo-3,4-dihydro-1H-2λ(6),1-benzothia-zine.

Project description:The asymmetric unit of the title compound, C(15)H(18)BrN(3)O(2)S, contains two independent mol-ecules in both of which the (thia-zine)C=N-N double bond exhibits an E conformation. The cyclo-hexyl rings adopt chair conformations while the thia-zine rings are in sofa conformations. The mean planes of these rings are oriented at dihedral angles of 64.43 (13) and 28.6 (2)° in the two independent mol-ecules while the aromatic and thia-zine rings are twisted by dihedral angles of 8.73 (8) and 13.07 (2)°, respectively. In the crystal, C-H⋯O and C-H⋯Br inter-actions connect mol-ecules into chains propagating along the a axis.

| S-EPMC3393904 | 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-literature

Methyl 4-hy-droxy-2-meth-oxy-carbonyl-methyl-1,1-dioxo-1,2-dihydro-1λ,2-benzothia-zine-3-carboxyl-ate.

Project description:There are two independent mol-ecules in the asymmetric unit of the title compound, C(13)H(13)NO(7)S, which have almost identical geometries. The thia-zine ring adopts a sofa conformation in both mol-ecules and the mol-ecular conformations are stabilized by intramolecular O-H⋯O hydrogen bonds. Inter-molecular C-H⋯O hydrogen bonds stabilize the crystal packing.

| S-EPMC3200958 | biostudies-literature