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Crystal structures of methyl 3,5-di-bromo-4-cyano-benzoate and methyl 3,5-di-bromo-4-iso-cyano-benzoate.

ABSTRACT: The title crystals, C9H5Br2NO2, are the first reported 2,6-dihalophenyl cyanide-isocyanide pair that have neither three- nor two-dimensional isomorphism. Both crystals contain contacts between the carbonyl O atom and a Br atom. In the crystal of the cyanide, R22(10) inversion dimers form based on C?N?Br contacts, a common packing feature in this series of crystals. In the isocyanide, the corresponding N?C?Br contacts are not observed. Instead, the iso-cyano C atom forms contacts with the meth-oxy C atom. RNC was refined as a two-component pseudo-merohedral twin.

SUBMITTER: Noland WE

PROVIDER: S-EPMC5947800 | biostudies-other | 2018 Mar

REPOSITORIES: biostudies-other

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Crystal structures of methyl 3,5-di-bromo-4-cyano-benzoate and methyl 3,5-di-bromo-4-iso-cyano-benzoate.

Noland Wayland E WE Herzig Ryan J RJ Engwall Abigail J AJ Jensen Renee C RC Tritch Kenneth J KJ

Acta crystallographica. Section E, Crystallographic communications 20180213 Pt 3

The title crystals, C9H5Br2NO2, are the first reported 2,6-dihalophenyl cyanide-isocyanide pair that have neither three- nor two-dimensional isomorphism. Both crystals contain contacts between the carbonyl O atom and a Br atom. In the crystal of the cyanide, R22(10) inversion dimers form based on C≡N⋯Br contacts, a common packing feature in this series of crystals. In the isocyanide, the corresponding N≡C⋯Br contacts are no ...[more]

PMID: 29765720

Similar Datasets

A 2:1 co-crystal of 3,5-di-bromo-4-cyano-benzoic acid and anthracene.

Project description:The title co-crystal, C8H3Br2NO2·0.5C14H10, was self-assembled from a 2:1 mixture of the components in slowly evaporating di-chloro-methane. The mol-ecules adopt a sheet structure parallel to (1-12) in which carb-oxy hydrogen-bonded dimers and anthracene mol-ecules stagger in both dimensions. Within the sheets, six individual cyano acid mol-ecules surround each anthracene mol-ecule. Cyano acid mol-ecules form one of the two possible R22(10) rings between neighboring cyano and bromo groups. Compared to the di-chloro analog [Britton (2012 ?). J. Chem. Crystallogr.42, 851-855], the dihedral angle between the best-fit planes of acid and anthracene mol-ecules has decreased from 7.1 to 0.9?(2)°.

| S-EPMC5683504 | biostudies-literature

Crystal structures of 2,6-di-bromo-4-methyl-benzo-nitrile and 2,6-di-bromo-4-methyl-phenyl isocyanide.

Project description:In the title crystals, C8H5Br2N, which are isomorphous, the steric bulk of the methyl group causes neighboring mol-ecules to become mutually inclined. This prevents the formation of planar or nearly planar sheets, which were observed in the tri-chloro and tri-bromo analogs. Instead of CN/NC?Br contacts, tetra-meric Br?Br contacts are observed. These contacts form tetra-gonally puckered sheets parallel to (001). The CN/NC and methyl groups are grouped at the peaks and troughs. Both mol-ecules lie across crystallographic mirror planes; thus, the methyl H atoms are disordered over two sets of sites with equal occupancy. The title nitrile is a redetermination. The refinement converged at R[F2 > 2?(F2)] = 0.020, whereas the original determination [Gleason & Britton, (1976 ?). Cryst. Struct. Commun.5, 229-232] had R = 0.112.

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Crystal structure studies of 4-ethyl-piperazin-1-ium 3,5-di-nitro-benzoate, 4-methyl-piperazin-1-ium 3,5-di-nitro-benzoate and 4-methyl-piperazin-1-ium 4-iodo-benzoate.

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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.

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Synthesis and crystal structures of 2-bromo-1,3-di-methyl-imidazolium iodides.

Project description:Attempts at direct bromination of 1,3-di-methyl-imidazolium salts were futile. The title compounds, 2-bromo-1,3-di-methyl-imidazolium iodide chloro-form 0.33-solvate, C5H8BrN2+·I-·0.33CHCl3, 2-bromo-1,3-di-methyl-imidazolium iodide di-chloro-methane hemisolvate, C5H8BrN2+·I-·0.5CH2Cl2, and 2-bromo-1,3-di-methyl-imidazolium iodide hemi(diiodide), C5H8BrN2+·I-·0.5I2, were obtained by methyl-ation of 2-bromo-1-methyl-imidazole. They crystallized as CHCl3, CH2Cl2 or I2 solvates/adducts. The Br atom acts as a σ-hole to accept short C-Br⋯I inter-actions. C-H⋯I hydrogen bonds are observed in each structure.

| S-EPMC5946976 | biostudies-literature

Methyl 3,5-dibromo-4-methyl-benzoate.

Project description:In the title compound, C(9)H(8)Br(2)O(2), the mol-ecule is essentially planar with an r.m.s. deviation of 0.0652?Å from the mean plane through all non-H atoms and a dihedral angle of 7.1?(2)° between the benzene ring plane and the carboxyl-ate substituent. In the crystal structure, weak C-H?Br hydrogen bonds and weak inter-molecular O?Br contacts [3.095?(2)?Å], link adjacent mol-ecules into layers parallel to (102). Additional weak inter-molecular C-H?O hydrogen bond inter-actions stack the layers above and below the mol-ecular plane and down the a axis.

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Methyl 2-methyl-3,5-dinitro-benzoate.

Project description:In the title compound, C(9)H(8)N(2)O(6), the methyl ester group is almost planar (r.m.s. deviation = 0.002 Å) and is oriented at a dihedral angle of 24.27 (16)° with respect to the benzene ring. The nitro groups make dihedral angles of 4.2 (5)° and 60.21 (11)° with the benzene ring. In the crystal, mol-ecules are linked by C-H⋯O inter-actions, resulting in zigzag chains.

| S-EPMC2979943 | biostudies-literature

2-{2-[5-(4-Cyano-5-di-cyano-methyl-idene-2,2-dimethyl-2,5-di-hydro-furan-3-yl)penta-2,4-dienyl-idene]-3,3-dimethyl-2,3-di-hydro-1H-indol-1-yl}ethyl 3,5-bis-(benz-yloxy)benzoate.

Project description:In the title mol-ecule, C48H42N4O5, a potential non-linear optical compound, the furan ring [r.m.s. deviation = 0.010?(1)?Å] and the indolyl-idene ring system [r.m.s. deviation = 0.013?(2)?Å] are inclined to one another by 18.52?(6)°. This is similar to the arrangement [16.51?(18)°] found for the N-hy-droxy-ethyl adduct of the title compound [Bhuiyan et al. (2011 ?). Mol. Cryst. Liq. Cryst. 548, 1-12]. Replacing the hy-droxy-ethyl group with 3,5-di-benzyl-oxybenzoate has not resulted in a non-centrosymmetric lattice arrangement or significant changes to the basic mol-ecular structure. In the crystal, mol-ecules are linked via pairs of C-H?N hydrogen bonds, forming inversion dimers with an R (2) 2(20) ring motif. The dimers are linked via C-H?O hydrogen bonds, forming C(17) chains along [010]. The chains are linked by further C-H?N hydrogen bonds, forming layers parallel to (001) and enclosing R 2 (2)(44) ring motifs. There are also C-H?? inter-actions present, stabilizing the inter-layer orientation of the pendant bis-(benz-yloxy)benzo-yloxy group.

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Cyano-methyl 4-(4-methyl-benzene-sulfonamido)-benzoate.

Project description:The title mol-ecule, C(16)H(14)N(2)O(4)S, adopts an L-shaped conformation, with the central C-S-N-C torsion angle being -69.1?(3)°. The two benzene rings form a dihedral angle of 89.94?(15)°. The mol-ecular conformation may be influenced by a weak intra-molecular C-H?O hydrogen bond which generates an S(6) ring motif. In the crystal, mol-ecules are linked by N-H?O and weak C-H?O hydrogen bonds, forming chains propagating along the b axis. Weak C-H?N hydrogen bonds connect the chains into a two-dimensional network parallel to (011). The crystal studied was an inversion twin, the ratio of components being 0.7?(1):0.3?(1).

| S-EPMC3344598 | biostudies-literature

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