Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Crystal structure determination, Hirshfeld surface analysis and energy frameworks of 6-phenyl-sulfonyl-6H-thieno[3,2-c]carbazole.

ABSTRACT: In the title compound, C₂₀H₁₃NO₂S₂, the carbazole ring system forms a dihedral angle of 89.08?(1)° with the sulfonyl-substituted phenyl ring. Intra-molecular C-H?O hydrogen bonds involving the sulfone O atoms and the carbazole moiety result in two S(6) rings. In the crystal, mol-ecules are linked via pairs of C-H?O hydrogen bonds forming inversion dimers with an R₂²(12) graph-set motif. Analysis of the Hirshfeld surfaces and two-dimensional fingerprint plots was used to explore the distribution of weak inter-molecular inter-actions in the crystal structure.

SUBMITTER: Mohamooda Sumaya U

PROVIDER: S-EPMC6038642 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Crystal structure determination, Hirshfeld surface analysis and energy frameworks of 6-phenyl-sulfonyl-6H-thieno[3,2-c]carbazole.

Mohamooda Sumaya U U Sankar E E Arasambattu MohanaKrishnan K K Biruntha K K Usha G G

Acta crystallographica. Section E, Crystallographic communications 20180605 Pt 7

In the title compound, C20H13NO2S2, the carbazole ring system forms a dihedral angle of 89.08 (1)° with the sulfonyl-substituted phenyl ring. Intra-molecular C-H⋯O hydrogen bonds involving the sulfone O atoms and the carbazole moiety result in two S(6) rings. In the crystal, mol-ecules are linked via pairs of C-H⋯O hydrogen bonds forming inversion dimers with an R22(12) graph-set motif. Analysis of the Hirshfe ...[more]

PMID: 30002878

Similar Datasets

6-Meth-oxy-9-phenyl-sulfonyl-2-(2-thien-yl)-9H-thieno[2,3-b]carbazole.

Project description:In the title compound, C(25)H(17)NO(3)S(3), the mean planes of the thieno[2,3-b]carbazole and phenyl rings are inclined at an angle of 63.6?(1)°. The mol-ecular structure features short intra-molecular C-H?O contacts and the crystal packing exhibits weak inter-molecular C-H?S and ?-? inter-actions [centroid-to-centroid distances 3.734?(2)-3.888?(2)?Å].

| S-EPMC2968599 | biostudies-literature

Crystal structure of ethyl 2-phenyl-9-phenyl-sulfonyl-9H-carbazole-3-carboxyl-ate.

Project description:In the title compound, C27H21NO4S, the dihedral angles between the carbazole ring system (r.m.s. deviation = 0.015 Å) and the sulfur-bonded and directly linked benzene rings are 79.98 (11) and 53.51 (18)°, respectively. The benzene rings subtend a dihedral angle of 48.4 (2)°. The ethyl side chain of the ester group has an extended conformation [C-O-C-C = -172.3 (3)°]. In the crystal, inversion dimers linked by pairs of weak C-H⋯O hydrogen bonds generate R 2 (2)(22) loops. The dimers are linked by weak C-H⋯π and π-π [centroid-to-centroid distances ranging from 3.5042 (14) to 3.888 (2) Å] inter-actions, thereby forming a three-dimensional supra-molecular network.

| S-EPMC4647343 | biostudies-literature

Crystal structures of two new carbazole derivatives: 12-(4-nitro-phen-yl)-7-phenyl-sulfonyl-7H-benzofuro[2,3-b]carbazole and 2-methyl-4-(4-nitro-phen-yl)-9-phenyl-sulfonyl-9H-thieno[2,3-b]carbazole.

Project description:The title compounds, C30H18N2O5S, (I), and C27H18N2O4S2, (II), are carbazole derivatives with a phenyl-sulfonyl group and a nitro-phenyl group attached to the carbazole moiety in identical positions in both mol-ecules. A benzo-furan ring system in (I) and a methyl-thio-phene ring in (II) are fused with the respective carbazole moieties on the same sides. The mean plane of the carbazole ring system makes a dihedral angle of 3.17?(7)° with the benzo-furan ring system in (I) and a dihedral angle of 3.39?(11)° with the methyl-thio-phene ring in (II), implying that both fused units are essentially planar. The mean planes of the carbazole ring systems in both the compounds are almost orthogonal to the respective nitro-substituted phenyl rings, making dihedral angles of 75.64?(10) and 77.63?(12)° in compounds (I) and (II), respectively. In (I), the phenyl-sulfonyl ring system is positionally disordered with a refined occupancy ratio of 0.63?(2):0.37?(2). In both compounds, the mol-ecular structures are stabilized by intra-molecular C-H?O hydrogen bonds, generating S(6) ring motifs with the sulfone group O atoms. In the crystal of compound (I), mol-ecules are linked by pairs of C-H?O hydrogen bonds, which generate R22(18) inversion dimers, and inter-connected by C(14) chains running along the c-axis direction, whereas in compound (II), the C-H?O hydrogen bonds generate R43(37) ring motifs. In the crystals of both compounds, C-H?O hydrogen-bonded sheets are formed lying parallel to (10-1). In addition, C-H?? and offset ?-? inter-actions [inter-centroid distance = 3.7158?(14)?Å in (I) and 3.9040?(15)?Å in (II)] are also present in the crystals of both compounds.

| S-EPMC5137598 | biostudies-literature

7-Phenyl-sulfonyl-7H-benzofurano[2,3-b]carbazole.

Project description:In the title compound, C(24)H(15)NO(3)S, the dihedral angle between the phenyl ring and the carbozole system is 74.91?(6)°. The S atom exhibits a distorted tetra-hedral geometry [N-S-C = 104.85?(8)°; O-S-O = 119.59?(9)°]. The crystal structure is established by weak inter-molecular ?-? inter-actions [centroid-centroid distances = 3.583?(2)-3.782?(2)?Å].

| S-EPMC3247568 | biostudies-literature

7,9-Dimethyl-5-phenyl-sulfonyl-5H-benzo[b]carbazole.

Project description:In the title compound, C(24)H(19)NO(2)S, the mean plane of the benzo[b]carbazole ring system makes a dihedral angle of 79.26?(5)° with the phenyl ring. The S atom is in a distorted tetra-hedral configuration. The crystal structure exhibits weak C-H?O and C-H?? inter-actions.

| S-EPMC2960676 | biostudies-literature

Crystal structures of three carbazole derivatives: 12-ethyl-7-phenyl-sulfonyl-7H-benzofuro[2,3-b]carbazole, (1), 2-(4,5-dimeth-oxy-2-nitro-phen-yl)-4-hy-droxy-9-phenyl-sulfonyl-9H-carbazole-3-carbaldehyde, (2), and 12-phenyl-7-phenyl-sulfonyl-7H-benzofuro[2,3-b]carbazole, (3).

Project description:The three title compounds, C26H19NO3S, (1), C27H20N2O8S, (2), and C30H19NO3S, (3), are carbazole derivatives, where (1) and (3) are heterocycle-containing carbazoles with a benzo-furan moiety fused to a carbazole unit. In (2), a di-meth-oxy-nitro-phenyl ring is attached to the carbazole moiety. In the three derivatives, a phenyl-sulfonyl group is attached to the N atom of the carbazole unit. Compound (1) crystallizes with two independent mol-ecules in the asymmetric unit (A and B). The carbazole skeleton in the three compounds is essentially planar. In compound (1), the benzene ring of the phenyl-sulfonyl moiety is almost orthogonal to the carbazole moiety, with dihedral angles of 85.42?(9) and 84.52?(9)° in mol-ecules A and B, respectively. The benzene ring of the phenyl-sulfonyl group in compounds (2) and (3) are inclined to the carbazole moiety, making dihedral angles of 70.73?(13) and 81.73?(12)°, respectively. The S atom has a distorted tetra-hedral configuration in all three compounds. In the crystals, C-H?O hydrogen bonds give rise to R22(12) inversion dimers for compound (1), and to R22(24) inversion dimers and R44(40) ring motifs for compound (2). The crystal packing in (1) also features C-H?? and ?-? inter-actions [shortest inter-centroid distance = 3.684?(1)?Å], leading to supra-molecular three-dimensional aggregation. In the crystal of compound (2), the combination of the various C-H?O hydrogen bonds leads to the formation of a three-dimensional network. In the crystal of compound (3), mol-ecules are linked by C-H?O hydrogen bonds, forming chains running parallel to the a axis, and the chains are linked by C-H?? inter-actions, forming corrugated sheets parallel to the ab plane.

| S-EPMC5137599 | biostudies-literature

8,9-Dimeth-oxy-5-phenyl-sulfonyl-5H-benzo[b]carbazole.

Project description:In the title compound, C(24)H(19)NO(4)S, the benzocarbazole ring system is planar (r.m.s. deviation = 0.016?Å) and forms a dihedral angle of 78.54?(4)° with the sulfonyl-bound phenyl ring. Intra-molecular C-H?O inter-actions are observed. A C(8) chain running along the b axis is formed via inter-molecular C-H?O hydrogen bonds. The chains are linked via weak C-H? ? inter-actions.

| S-EPMC2979030 | biostudies-literature

9-Meth-oxy-5-phenyl-sulfonyl-5H-benzo[b]carbazole.

Project description:In the title compound, C(23)H(17)NO(3)S, the mean plane of the benzo[b]carbazole ring system makes a dihedral angle of 77.17?(4)° with the phenyl ring. The S atom is in a distorted tetra-hedral configuration. There are three intra-molecular C-H?O inter-actions forming five- and six-membered rings with graph-set motifs S(5) and S(6), respectively.

| S-EPMC2960649 | biostudies-literature

5-Methyl-12-phenyl-sulfonyl-12H-naphtho-[1,2-b]carbazole.

Project description:In the title compound, C(27)H(19)NO(2)S, the naphtho-carbazole unit is approximately planar (r.m.s. deviation = 0.002 Å) except for the N atom, which is displaced by 0.122 (1) Å out of the mean plane. The dihedral angle between the naphtho-carbazole mean plane and the phenyl ring of the phenyl-sulfonyl substituent is 83.16 (3)°. An inter-molecular C-H⋯π inter-action involving the phenyl group and the pyrrole ring is observed in the crystal structure.

| S-EPMC3239104 | biostudies-literature

Crystal structure of 2-(2,4-di-chloro-phen-yl)-4-hydroxy-9-phenyl-sulfonyl-9H-carbazole-3-carbaldehyde.

Project description:In the title compound, C25H15Cl2NO4S, the di-chloro-phenyl ring is twisted by 68.69 (11)° from the mean plane of the carbazole ring system [r.m.s. deviation = 0.084 (2)°]. The hy-droxy group is involved in an intra-molecular O-H⋯O hydrogen bond, which generates an S(6) graph-set motif. In the crystal, pairs of C-H⋯Cl hydrogen bonds link mol-ecules into inversion dimers with an R (2) 2(26) motif. Weak C-H⋯O inter-actions further link these dimers into ribbons propagating in [100].

| S-EPMC4257421 | biostudies-literature