Browse
Submit Data
Databases
API
Help

Dataset Information

9 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Crystal structure of meso-3,3'-(1,4-phenyl-ene)bis-(2-phenyl-2,3,5,6-tetra-hydro-4H-1,3-thia-zin-4-one).

ABSTRACT: The crystal structure of the title compound - meso-C₂₆H₂₄N₂O₂S₂ with two stereocenters - has half the mol-ecule in the asymmetric unit with the other half generated by a crystallographic center of inversion. The thia-zine ring is in a conformation that is between half-chair and envelope [? = 52.51?(17)°]. The phenyl ring on the 2-carbon atom of the thia-zine ring is pseudo-axial. The central phenyl ring of the mol-ecule is close to orthogonal to the phenyl rings on either side with an angle of 76.85?(11)° between those planes. In the crystal, pairwise, weak C-H?O hydrogen bonds between the central phenyl ring and the oxygen atoms of neighboring mol-ecules result in continuous strips propagating along the a-axis direction. Hydro-phobic inter-actions of the C-H?? type are also observed.

SUBMITTER: Yennawar HP

PROVIDER: S-EPMC6176446 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Crystal structure of meso-3,3'-(1,4-phenyl-ene)bis-(2-phenyl-2,3,5,6-tetra-hydro-4H-1,3-thia-zin-4-one).

Yennawar Hemant P HP Moyer Quentin J QJ Silverberg Lee J LJ

Acta crystallographica. Section E, Crystallographic communications 20180928 Pt 10

The crystal structure of the title compound - meso-C26H24N2O2S2 with two stereocenters - has half the mol-ecule in the asymmetric unit with the other half generated by a crystallographic center of inversion. The thia-zine ring is in a conformation that is between half-chair and envelope [θ = 52.51 (17)°]. The phenyl ring on the 2-carbon atom of the thia-zine ring is pseudo-axial. The central phenyl ring of the mol-ecule is close to or ...[more]

PMID: 30319809

Similar Datasets

2,3-Diphenyl-2,3,5,6-tetra-hydro-4H-1,3-thia-zin-4-one.

Project description:The six-membered thia-zine ring in the title compound, C16H15NOS, adopts a half-chair conformation, with the S atom forming the back of the chair. The base of the chair has a slight twist reflected in the r.m.s. deviation (0.0756 Å) of those five atoms from the plane defined by them. The phenyl substituents are almost perpendicular to each other [dihedral angle 87.06 (9)°]. In the crystal, mol-ecules are linked into chains parallel to the c axis through C-H⋯O inter-actions.

| S-EPMC3998299 | biostudies-literature

Synthesis and crystal structure of racemic (R*,R*)-2,2'-(1,4-phenyl-ene)bis-(3-phenyl-2,3,5,6-tetra-hydro-4H-1,3-thia-zin-4-one).

Project description:In the racemic title compound, C26H24N2O2S2, one of the thia-zine rings shows a twisted boat conformation (Q = 0.743 Å, θ = 92.1°) and the other a half-chair puckering (Q = 0.669 Å, θ = 54.3°). The terminal phenyl rings are almost parallel to each other [dihedral angle 21.71 (10)°]. Both of these rings are orthogonal to the central phenyl ring, subtending a dihedral angle of about 78° in each case. The extended structure is consolidated by C-H⋯O and C-H⋯S hydrogen bonds as well as aromatic ring inter-actions of parallel-displaced and T-type. The mol-ecule has approximate C2 local symmetry but this is not carried over to its three-dimensional structure or the inter-molecular inter-actions.

| S-EPMC8647733 | biostudies-literature

Spontaneous resolution and crystal structure of (2S)-2-(3-nitro-phen-yl)-3-phenyl-2,3,5,6-tetra-hydro-4H-1,3-thia-zin-4-one; crystal structure of rac-2-(4-nitro-phen-yl)-3-phenyl-2,3,5,6-tetra-hydro-4H-1,3-thia-zin-4-one.

Project description:The crystal structures of isomeric rac-2-(4-nitro-phen-yl)-3-phenyl-2,3,5,6-tetra-hydro-4H-1,3-thia-zin-4-one (C16H14N2O3S) (1) and (2S)-2-(3-nitro-phen-yl)-3-phenyl-2,3,5,6-tetra-hydro-4H-1,3-thia-zin-4-one (C16H14N2O3S) (2) are reported here. While 1 crystallizes in a centrosymmetric space group, the crystal of 2 chosen for data collection has mol-ecules only with (2S) chirality. This is the result of spontaneous resolution during crystallization, as the synthesis produces a racemic mixture. A crystal with (2R) mol-ecules was also found in the same crystallization vial (structure factors available). The six-membered thia-zine ring in both 1 and 2 displays an envelope conformation with the S atom forming the flap. The aryl rings in both structures adopt an approximate V shape with angles between their planes of 46.97 (14)° in 1 and 58.37 (10)° in 2. In both structures, the mol-ecules form layers in the ab plane. Within such a layer in 1, one of the O atoms of the nitro-phenyl group accepts a C-H⋯O hydrogen bond from the CH group at position 5 of the thia-zine ring of a mol-ecule of opposite chirality, forming chains along the a-axis direction. Each of the thia-zine rings also participate in C-H⋯O bonds with the same carbon atom as above, resulting in chains along the b-axis direction, albeit of monochiral type. Adjacent layers are consolidated along the c-axis direction by pairs of parallel hydrogen bonds (C-H⋯O type) between the nitro-phenyl groups of enanti-omers. In 2, the two C-H⋯O hydrogen bonds contribute to chain formation along the b-axis direction. Weak edge-to-face inter-actions between the aryl groups of neighbouring mol-ecules in 1, and C-H⋯π inter-actions between a thia-zine ring CH group and a phenyl group of a neighboring mol-ecule in 2 are also observed.

| S-EPMC5946966 | biostudies-literature

Crystal structures of 2-(4-nitro-phen-yl)-3-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one and 2-(2-nitro-phen-yl)-3-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one.

Project description:The crystal structures are reported of the isomeric compounds 2-(4-nitro-phen-yl)-3-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one, (I), and 2-(2-nitro-phen-yl)-3-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one, (II), both C20H14N2O3S, being the para-nitro and ortho-nitro forms, respectively, the meta-form of which is known [Yennawar et al. (2013). Acta Cryst. E69, o1679]. The six-membered thia-zone ring fused with a benzene ring displays a screw-boat conformation with a total puckering amplitude of 0.627 (1) Å in (I), and a near screw-boat conformation with a total puckering amplitude of 0.600 (1) Å in (II). The dihedral angles between the planes of the substituent nitrophenyl and phenyl and rings with the benzene ring of the parent benzo-thia-zone moiety are 75.93 (5) and 82.61 (5)° [in (I)], and 76.79 (6) and 71.66 (6)° [in (II)]. Weak inter-molecular C-H⋯O hydrogen-bonding inter-actions between aromatic H-atom donors and both a nitro-O atom and a thia-zone O-atom acceptor in (I) and a thia-zone O atom in (II) are present, forming in (I) a centrosymmetric 22-membered cyclic dimer which is extended through a similar inversion-related 14-membered cyclic hydrogen-bonding association into a zigzag chain structure extending along c. In (II), a single inter-molecular C-H⋯O hydrogen bond gives a chain structure extending along b. In addition, weak C-H⋯π inter-actions are present in both structures [minimum C⋯ring-centroid separations = 3.630 (2) and 3.581 (2) Å, respectively].

| S-EPMC4438845 | biostudies-literature

2-(3-Nitro-phen-yl)-3-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one.

Project description:The title compound, C20H14N2O3S, has three aromatic rings, viz. (i) a phenyl ring, (ii) a 3-nitro-phenyl and (iii) a 1,3-benzo-thia-zine fused-ring system. The dihedral angle between (i) and (ii) is 85.31?(15)°, between (ii) and (iii) is 81.33?(15)° and between (i) and (iii) is 75.73?(15)°. The six-membered 1,3-thia-zine ring has an envelope conformation with the C atom in the 2-position forming the flap. In the crystal, mol-ecules are linked by weak C-H?O inter-actions, forming a three-dimensional network.

| S-EPMC3884335 | biostudies-literature

2,3-Diphenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one.

Project description:In the title compound, C20H15NOS, the dihedral angle between the phenyl rings is 74.25 (6)°. The six-membered 1,3-thia-zine ring has an envelope conformation with the C atom at the 2-position forming the flap. The crystal structure features weak C-H⋯O inter-actions, which lead to the formation of a tape motif along [110].

| S-EPMC3998534 | biostudies-literature

Crystal structures of three substituted 3-aryl-2-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-ones.

Project description:Three ring-substituted 3-aryl analogs of 2-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one, namely 3-(4-meth-oxy-phen-yl)-2-phenyl-4H-1,3-benzo-thia-zin-4-one, C21H17NO2S, (I), 2-phenyl-3-[4-(tri-fluoro-meth-yl)phen-yl]-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one toluene hemisolvate, C21H14F3NOS·0.5C7H8, (II), and 3-(3-bromo-phen-yl)-2-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one toluene hemisolvate, C20H14BrNOS·0.5C7H8, (III), were synthesized and their crystal structures determined. The hemisolvates differ in that in (II), the asymmetric unit comprises two molecules of the benzo-thia-zinone compound and a toluene solvent mol-ecule, whereas in (III), the unit comprises one benzo-thia-zinone mol-ecule and a half-occupancy toluene solvent mol-ecule. All crystals are of racemic mixtures of the chiral 2-C atom of the thia-zine moiety, which in all structures has a screw-boat puckering, with the puckering amplitude values within the range 0.575-0.603 Å. In all three structures, the benzene plane of the benzo-thia-zine system makes a dihedral angle in the range 78.60 (5) to 98.40 (5)° with the unsubstituted benzene plane and in the range 70.50 (1) to 121.00 (5)° with the substituted benzene plane. The CF3 substituent group in one of the mol-ecules of (II) shows positional disorder, with an occupancy ratio of 0.57 (3):0.43 (3). In the crystals of (I) and (II), weak inter-molecular C-H⋯O inter-actions are present, giving in (I), mol-ecules arranged in a plane parallel to (010), and in (II), chains along a. In addition, all three structures show weak C-H⋯π inter-actions involving various aromatic rings.

| S-EPMC4971851 | biostudies-literature

Crystal structures of two solvated 2-aryl-3-phenyl-2,3-di-hydro-4H-pyrido[3,2-e][1,3]thia-zin-4-ones.

Project description:The synthesis and crystal structures of 2-(4-fluoro-phen-yl)-3-phenyl-2,3-di-hydro-4H-pyrido[3,2-e][1,3]thia-zin-4-one toluene hemisolvate (1), C19H13FN2OS·0.5C7H8, and 2-(4-nitro-phen-yl)-3-phenyl-2,3-di-hydro-4H-pyrido[3,2-e][1,3]thia-zin-4-one iso-propanol 0.25-solvate 0.0625-hydrate (2), C19H13N3O3S·0.25C3H7O·0.0625H2O, are reported. Both are racemic mixtures (centrosymmetric crystal structures) of the individual com-pounds and incorporate solvent mol-ecules in their structures. Compound 2 has four thia-zine mol-ecules in the asymmetric unit. All the thia-zine rings in this study show an envelope pucker, with the C atom bearing the substituted phenyl ring displaced from the other atoms. The phenyl and aryl rings in each of the mol-ecules are roughly orthogonal to each other, with dihedral angles of about 75°. The extended structures of 1 and 2 are consolidated by C-H⋯O and C-H⋯N(π), as well as T-type (C-H⋯π) inter-actions. Parallel aromatic ring inter-actions (π-π stacking) are observed only in 2.

| S-EPMC6829726 | biostudies-literature

3,3'-Di-tert-butyl-1,1'-[1,3-phenyl-enebis(methyl-ene)]diurea.

Project description:The title compound, C(18)H(30)N(4)O(2), contains two tert-butyl urea groups, each connected to a benzene ring though a methyl-ene group. One of the groups occupies a position almost normal to the aromatic plane with a C-N-C-C torsion angle of -94.4?(4)°, while the other is considerably twisted from the ring with a C-N-C-C torsion angle of -136.1?(4)°. In the crystal, pairs of mol-ecules are connected to each other, forming centrosymmetric dimers in which two NH groups of one mol-ecule act as hydrogen-bond donors to one carbonyl O atom of the other mol-ecule. The dimers are linked into sheets parallel to (100) by N-H?O hydrogen bonds involving the remaining N-H and C=O groups.

| S-EPMC2983681 | biostudies-literature

3,3'-Diethyl-1,1'-(1,4-phenyl-ene-dimethyl-ene)diimidazol-3-ium bis-(hexa-fluoro-phosphate).

Project description:In the title mol-ecular salt, C(18)H(24)N(4) (2+)·2PF(6) (-), the complete dication is generated by a crystallographic inversion centre. The central benzene ring makes a dihedral angle of 77.19 (9)° with each of the imidazole rings. In the crystal, C-H⋯F inter-actions link the cations and anions into layers lying parallel to the bc plane. The hexa-fluoro-phosphate anion is disordered over two sets of sites in a 0.520 (11):0.480 (11) ratio.

| S-EPMC3394059 | biostudies-literature