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Crystal structures of 4-chloro-phenyl N-(3,5-di-nitro-phen-yl)carbamate and phenyl N-(3,5-di-nitro-phen-yl)carbamate.

ABSTRACT: The title compounds, C13H8ClN3O6, (I), and C13H9N3O6, (II), differ in the orientation of the two aromatic rings. In (I), they are essentially coplanar, making a dihedral angle of 8.2 (1)°, while in (II), they are inclined to one another by 76.2 (1)°. The two nitro groups are essentially coplanar with the attached benzene rings, as indicated by the dihedral angles of 1.4 (2) and 2.3 (2)° in (I), and 4.96 (18) and 5.4 (2)° in (II). The carbamate group is twisted slightly from the attached benzene ring, with a C-N-C-O torsion angle of -170.17 (15)° for (I) and 168.91 (13)° for (II). In the crystals of of both compounds, mol-ecules are linked via N-H⋯O hydrogen bonds, forming chains propagating along [010]. In (I), C-H⋯O hydrogen bonds also link mol-ecules within the chains. The crystal packing in (I) also features a very weak π-π inter-action [centroid-centroid distance = 3.7519 (9) Å].

SUBMITTER: Raja R

PROVIDER: S-EPMC4518992 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystal structures of isomeric 3,5-di-chloro-N-(2,3-di-methyl-phen-yl)benzene-sulfonamide, 3,5-di-chloro-N-(2,6-di-methyl-phen-yl)benzene-sulfonamide and 3,5-di-chloro-N-(3,5-di-methyl-phen-yl)benzene-sulfonamide.

Project description:The crystal structures of three isomeric compounds of formula C14H13Cl2NO2S, namely 3,5-di-chloro-N-(2,3-di-methyl-phen-yl)-benzene-sulfonamide (I), 3,5-di-chloro-N-(2,6-di-methyl-phen-yl)benzene-sulfonamide (II) and 3,5-di-chloro-N-(3,5-di-methyl-phen-yl)benzene-sulfonamide (III) are described. The mol-ecules of all the three compounds are U-shaped with the two aromatic rings inclined at 41.3?(6)° in (I), 42.1?(2)° in (II) and 54.4?(3)° in (III). The mol-ecular conformation of (II) is stabilized by intra-molecular C-H?O hydrogen bonds and C-H?? inter-actions. The crystal structure of (I) features N-H?O hydrogen-bonded R22(8) loops inter-connected via C(7) chains of C-H?O inter-actions, forming a three-dimensional architecture. The structure also features ?-? inter-actions [Cg?Cg = 3.6970?(14)?Å]. In (II), N-H?O hydrogen-bonded R22(8) loops are inter-connected via ?-? inter-actions [inter-centroid distance = 3.606?(3)?Å] to form a one-dimensional architecture running parallel to the a axis. In (III), adjacent C(4) chains of N-H?O hydrogen-bonded mol-ecules running parallel to [010] are connected via C-H?? inter-actions, forming sheets parallel to the ab plane. Neighbouring sheets are linked via offset ?-? inter-actions [inter-centroid distance = 3.8303?(16)?Å] to form a three-dimensional architecture.

| S-EPMC5418781 | biostudies-literature

Crystal structure of phenyl N-(4-nitro-phen-yl)carbamate.

Project description:The asymmetric unit of the title compound, C13H10N2O4, contains two independent mol-ecules (A and B). The dihedral angle between the aromatic rings is 48.18 (14)° in mol-ecule A and 45.81 (14)° in mol-ecule B. The mean plane of the carbamate N-C(=O)-O group is twisted slightly from the attached benzene and phenyl rings, making respective dihedral angles of 12.97 (13) and 60.93 (14)° in A, and 23.11 (14) and 59.10 (14)° in B. In the crystal, A and B mol-ecules are arranged alternately through N-H⋯O hydrogen bonds and C-H⋯π inter-actions, forming chains along the a axis. The chains are further linked by C-H⋯O hydrogen bonds into a double-chain structure.

| S-EPMC4719927 | biostudies-literature

Isotypic crystal structures of 2,6-di-bromo-N,N-bis-(4-nitro-phen-yl)aniline and 2,6-di-chloro-N,N-bis-(4-nitro-phen-yl)aniline.

Project description:In the mol-ecules of the two isotypic title compounds, C18H11Br2N3O4 (I) and C18H11Cl2N3O4 (II), the tri-phenyl-amine N atoms show no sign of pyramidalization, with marginal displacements of the N atoms from the mean plane of the three connecting C atoms: 0.0058?(13)?Å for the Br compound (I) and 0.0074?(9)?Å for the Cl compound (II). In the crystals, mol-ecules are linked through C-H?O hydrogen bonds between phenyl rings and nitro groups and by X?O (X = Br, Cl) inter-actions, that are shorter than the sum of the van der Waals radii, leading to a three-dimensional network.

| S-EPMC4158496 | biostudies-literature

Phenyl N-[4-chloro-3-(trifluoro-meth-yl)phen-yl]carbamate.

Project description:In the mol-ecule of the title compound, C(14)H(9)ClF(3)NO(2), the aromatic rings are oriented at a dihedral angle of 66.49?(3)°. Intra-molecular C-H?F and C-H?O inter-actions result in the formation of one planar five- and one non-planar six-membered ring. In the crystal structure, inter-molecular N-H?O hydrogen bonds link the mol-ecules into chains.

| S-EPMC2968454 | biostudies-literature

Crystal structures of ethyl {2-[4-(4-iso-propyl-phen-yl)thia-zol-2-yl]phen-yl}carbamate and ethyl {2-[4-(3-nitro-phen-yl)thia-zol-2-yl]phen-yl}carbamate.

Project description:The title compounds, C21H22N2O2S (I) and C18H15N3O4S (II), are structural analogs of the alkaloid Thio-sporine B. Both mol-ecules adopt a near-planar V-shaped conformation, which is consolidated by intra-molecular N-H?N and C-H?O hydrogen bonds. The crystal structure of (I) consists of mlecular stacks along the a axis, in which the mol-ecules are linked to each other by ?(S)??(C) inter-actions. In the crystal of (II), mol-ecules are linked into chains by C-H?O hydrogen bonds and the chains are cross-linked into (100) sheets by ?-? stacking inter-actions.

| S-EPMC5120716 | biostudies-literature

Phenyl N-(5-chloro-2-nitro-phenyl)carbamate.

Project description:In the title compound, C(13)H(9)ClN(2)O(4), the dihedral angle between the benzene rings is 79.5 (1)°. The mean plane of the carbamate group makes angles of 7.4 (2) and 73.6 (2)° with the mean planes of the two benzene rings. In the crystal, weak C-H⋯O inter-actions are observed between the mol-ecules, connecting them into a two-dimensional network.

| S-EPMC3414992 | biostudies-literature

Crystal structure of phenyl N-(3,5-di-methyl-phenyl)carbamate.

Project description:The asymmetric unit of the title compound, C15H15NO2, contains two independent mol-ecules (A and B). The di-methyl-phenyl ring, the phenyl ring and the central carbamate N-C(=O)-O group are not coplanar. In mol-ecule A, the di-methyl-phenyl and phenyl rings are inclined to the carbamate group mean plane by 27.71?(13) and 71.70?(4)°, respectively, and to one another by 84.53?(13)°. The corresponding dihedral angles in mol-ecule B are 34.33?(11), 66.32?(13) and 85.48?(12)°, respectively. In the crystal, the A and B mol-ecules are arranged alternately linked through N-H?O(carbon-yl) hydrogen bonds, forming -A-B-A-B- chains, which extend along [100]. Within the chains and linking neighbouring chains there are C-H?? inter-actions present, forming columns along the a-axis direction. The columns are linked by offset ?-? stacking inter-actions, forming a three-dimensional network [shortest centroid-centroid distance = 3.606?(1)?Å].

| S-EPMC5458307 | biostudies-other

Crystal structures and Hirshfeld surface analyses of the two isotypic compounds (<i>E</i>)-1-(4-bromo-phen-yl)-2-[2,2-di-chloro-1-(4-nitro-phen-yl)ethen-yl]diazene and (<i>E</i>)-1-(4-chloro-phen-yl)-2-[2,2-di-chloro-1-(4-nitro-phen-yl)ethen-yl]diazene.

Project description:In the two isotypic title compounds, C14H8BrCl2N3O2, (I), and C14H8Cl3N3O2, (II), the substitution of one of the phenyl rings is different [Br for (I) and Cl for (II)]. Aromatic rings form dihedral angles of 60.9 (2) and 64.1 (2)°, respectively. Mol-ecules are linked through weak X⋯Cl contacts [X = Br for (I) and Cl for (II)], C-H⋯Cl and C-Cl⋯π inter-actions into sheets parallel to the ab plane. Additional van der Waals inter-actions consolidate the three-dimensional packing. Hirshfeld surface analysis of the crystal structures indicates that the most important contributions for the crystal packing for (I) are from C⋯H/H⋯C (16.1%), O⋯H/H⋯O (13.1%), Cl⋯H/H⋯Cl (12.7%), H⋯H (11.4%), Br⋯H/H⋯Br (8.9%), N⋯H/H⋯N (6.9%) and Cl⋯C/C⋯Cl (6.6%) inter-actions, and for (II), from Cl⋯H / H⋯Cl (21.9%), C⋯H/H⋯C (15.3%), O⋯H/H⋯O (13.4%), H⋯H (11.5%), Cl⋯C/C⋯Cl (8.3%), N⋯H/H⋯N (7.0%) and Cl⋯Cl (5.9%) inter-actions. The crystal of (I) studied was refined as an inversion twin, the ratio of components being 0.9917 (12):0.0083 (12).

| S-EPMC6690453 | biostudies-literature

Crystal structure of 3,5-di-methyl-phenyl 2-nitro-benzene-sulfonate.

Project description:The title compound, C14H13NO5S, was synthesized via a nucleophilic substitution reaction between 3,5-di-methyl-phenol and 2-nitro-benzene-sulfonyl chloride. The aromatic rings attached to the SO3 group are oriented in a gauche fashion around the ester S-O bond, with a C-S-O-C torsion angle of 84.68?(11)°. The mol-ecules form centrosymmetric dimers via ?-? stacking inter-actions between 3,5-di-methyl-phenyl groups (centroid-centroid distance = 3.709?Å). An inter-molecular S=O?N inter-action between the sulfonyl and nitro groups, with an O?N distance of 2.9840?(18)?Å, organizes the dimers into columns extending along [011]. These columns are further assembled into (111) layers through C-H?O inter-actions.

| S-EPMC4555383 | biostudies-literature

2-(4,5-Di-chloro-2-nitro-phen-yl)-4-meth-oxy-3-methyl-9-phenyl-sulfon-yl-9H-carbazole.

Project description:In the title compound, C26H18Cl2N2O5S, the carbazole ring system is essentially planar with a maximum deviation of 0.0498?(16)?Å for the N atom. The carbazole ring system is almost orthogonal to the phenyl-sulfonyl and di-chloro-substituted nitro-phenyl rings, making dihedral angles of 84.23?(7) and 85.46?(12)°, respectively. The mol-ecular structure features intra-molecular C-H?O inter-actions, which generate two S(6) ring motifs. In the crystal, mol-ecules are linked by C-Cl?O halogen bonds [3.016?(3)?Å, 166.63?(5)°], which generate infinite C(8) chains running parallel to [010].

| S-EPMC3998356 | biostudies-literature

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