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N-(2-Chloro-eth-yl)pyrazine-2-carboxamide.

ABSTRACT: In the title mol-ecule, C(7)H(8)ClN(3)O, the pyrazine and amide groups are almost co-planar [N-C-C-N torsion angle = -2.4?(2) °], a conformation stabilized by an intra-molecular N-H?N hydrogen bond. The chloro-ethyl group lies out of the plane [N-C-C-Cl = -65.06?(17) °]. In the crystal, the presence of N-H?N hydrogen bonds leads to the formation of a C(6) supra-molecular chain along the b axis. The carbonyl-O atom accepts two C-H?O inter-actions. These, plus Cl?Cl short contacts [3.3653?(6)?Å], consolidate the packing of the chains in the crystal.

SUBMITTER: da Silva Lima CH

PROVIDER: S-EPMC3009184 | biostudies-literature | 2010 Oct

REPOSITORIES: biostudies-literature

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N-(2-Chloro-eth-yl)pyrazine-2-carboxamide.

da Silva Lima Camilo H CH de Souza Marcus V N MV Wardell Solange M S V SM Wardell James L JL Tiekink Edward R T ER

Acta crystallographica. Section E, Structure reports online 20101023 Pt 11

In the title mol-ecule, C(7)H(8)ClN(3)O, the pyrazine and amide groups are almost co-planar [N-C-C-N torsion angle = -2.4 (2) °], a conformation stabilized by an intra-molecular N-H⋯N hydrogen bond. The chloro-ethyl group lies out of the plane [N-C-C-Cl = -65.06 (17) °]. In the crystal, the presence of N-H⋯N hydrogen bonds leads to the formation of a C(6) supra-molecular chain along the b axis. The carbonyl-O atom accepts two C-H⋯O inter-actions. These, plus Cl⋯Cl short contacts [3.3653 (6) Å], ...[more]

PMID: 21589067

Similar Datasets

Crystal structures of N-(pyridin-2-ylmeth-yl)pyrazine-2-carboxamide (monoclinic polymorph) and N-(pyridin-4-ylmeth-yl)pyrazine-2-carboxamide.

Project description:The title compounds, C11H10N4O (HL1) and C11H10N4O (HL2), are pyridine 2-ylmethyl and 4-ylmethyl derivatives, respectively, of pyrazine-2-carboxamide. HL1 was measured at 153?K and crystallized in the monoclinic space group P21/c with Z = 4. There has been a report of the same structure measured at room temperature but assumed to crystallize in the triclinic space group P-1 with Z = 4 [Sasan et al. (2008 ?). Monatsh. Chem. 139, 773-780]. In HL1, the pyridine ring is inclined to the pyrazine ring by 61.34?(6)°, while in HL2 this dihedral angle is 84.33?(12)°. In both mol-ecules, there is a short N-H?N inter-action involving the pyrazine carboxamide unit. In the crystal of HL1, mol-ecules are linked by N-H?N hydrogen bonds, forming inversion dimers with an R 2 (2)(10) ring motif. The dimers are linked via bifurcated-acceptor C-H?O hydrogen bonds, forming sheets lying parallel to (102). The sheets are linked via C-H?N hydrogen bonds, forming a three-dimensional structure. In the crystal of HL2, mol-ecules are linked by N-H?N and C-H?N hydrogen bonds to form chains propagating along [010]. The chains are linked via C-H?O hydrogen bonds, forming sheets lying parallel to (100). Within the sheets there are ?-? inter-actions involving neighbouring pyrazine rings [inter-centroid distance = 3.711?(15)?Å]. Adjacent sheets are linked via parallel slipped ?-? inter-actions involving inversion-related pyridine rings [inter-centroid distance = 3.6395?(17)?Å], forming a three-dimensional structure.

| S-EPMC4120586 | biostudies-literature

3,6-Bis(4-chloro-phen-yl)-N,N-bis-(1-phenyl-eth-yl)-1,2,4,5-tetra-zine-1,4-di-carboxamide.

Project description:In the title mol-ecule, C(32)H(28)Cl(2)N(6)O(2), the amide-substituted N atoms of the tetra-zine ring deviate from the approximate plane of the four other atoms in the ring by 0.468?(3) and 0.484?(3)?Å, forming a boat conformation. The dihedral angle between the two phenyl rings is 67.0?(1)° and that between the two chloro-substituted benzene rings is 73.8?(1)°. Two intra-molecular N-H?N hydrogen bonds are observed.

| S-EPMC3297322 | biostudies-literature

1-[2-(Pyrazin-2-ylsulfan-yl)eth-yl]pyrazine-2(1H)-thione.

Project description:The title multifunctional twisted organic ligand, C(10)H(10)N(4)S(2), contains a short C=S bond [1.671?(2)?Å]. The dihedral angle between the two pyrazine rings is 39.83?(6)°. In the crystal, inter-molecular C-H?N and C-H?S hydrogen bonds result in the formation of a supra-molecular network.

| S-EPMC3051550 | biostudies-literature

(E)-2,4-Dichloro-6-{1-[(2-chloro-eth-yl)imino]-eth-yl}phenol.

Project description:The title Schiff base compound, C(10)H(10)Cl(3)NO, was prepared by the condensation of 1-(3,5-dichloro-2-hy-droxy-phen-yl)ethanone with chloro-ethyl-amine. The imine adopts an E configuration with respect to the C=N bond. The H atom of the phenolic OH group is disordered over two positions with site occupation factors of 0.52?(7) and 0.48?(7), respectively, and the major occupancy component is involved in an intramolecular N-H?O hydrogen bond. The compound therefore exists in an iminium-phenolate as well as in the imino-phenol form. In the crystal, mol-ecules are connected by C-H?O and C-H?Cl hydrogen bonds and Cl?Cl inter-actions [3.7864?(9)?Å] into a three-dimensional network. In addition, inter-molecular ?-? stacking inter-actions [centroid-centroid distance = 4.4312?(9)?Å] are observed.

| S-EPMC3011393 | biostudies-literature

2,4-Di-chloro-N-[eth-yl(2-hy-droxy-eth-yl)carbamo-thio-yl]benzamide.

Project description:In the title compound, C12H14Cl2N2O2S, the mol-ecule adopts a cis conformation with respect to the di-chloro-benzoyl group against the thiono group about the C-N bond. However, the di-chloro-benzene group and the thio-urea moiety are twisted by 75.41?(8)°. An intra-molecular N-H?O hydrogen bond occurs between the amido H atom and hydroxyl O atom. In the crystal, O-H?S and O-H?O hydrogen bonds link the molecules, forming chains along the b-axis direction.

| S-EPMC3914078 | biostudies-literature

N-[2,6-Bis(1-methyl-eth-yl)phen-yl]pyridine-4-carboxamide.

Project description:In the title compound, C(18)H(22)N(2)O, the dihedral angle between the benzene ring and the pyridine ring is 80.0?(1)°. In the crystal, N-H?O hydrogen bonds connect the mol-ecules into chains along the b axis. The packing also features C-H?O and C-H?N hydrogen bonds and C-H?? interactions, one directed to the benzene ring and the other to the center of the pyridine ring.

| S-EPMC3470342 | biostudies-literature

N-(4-Chloro-phen-yl)morpholine-4-carboxamide.

Project description:In the title mol-ecule, C(11)H(13)ClN(2)O(2), the morpholine ring has a chair conformation. In the crystal, mol-ecules are linked into chains along [100] by N-H?O hydrogen bonds.

| S-EPMC3200746 | biostudies-literature

{4-Chloro-2-[(2-hy-droxy-eth-yl)imino-meth-yl]phenolato}{4-chloro-2-[(2-oxido-eth-yl)imino-meth-yl]phenolato}cobalt(III).

Project description:In the title mononuclear cobalt(III) compound, [Co(C(9)H(8)ClNO(2))(C(9)H(9)ClNO(2))], the Co(II) atom is six-coordinated by two imine N atoms, two phenolate O atoms, and one hy-droxy and one oxide O atom from two Schiff base ligands, forming an octa-hedral geometry. In the crystal structure, adjacent mol-ecules are linked through inter-molecular O-H?O hydrogen bonds. The 2-oxidoethyl group is disordered over two positions in a 0.638?(3):0.362?(3) ratio.

| S-EPMC3008055 | biostudies-literature

5-{2-(4-Chloro-phen-yl)-1-[2-(4-chloro-phen-yl)-1-(3,4,5-trimeth-oxy-phen-yl)eth-oxy]eth-yl}-1,2,3-trimeth-oxy-benzene.

Project description:The title compound, C(34)H(36)Cl(2)O(7), is a by-product from the reaction of 4-chloro-benzyl-zinc chloride with 3,4,5-trimeth-oxy-benzaldehyde. In each of the two 1,2-diphenyl-ethyl moieties, the two benzene rings are arranged in a trans conformation and make C(ar)-C-C-C(ar) torsion angles of 163.64 (19) and 174.43 (18)°. The crystal structure is stabilized by van der Waals inter-actions only.

| S-EPMC3343973 | biostudies-literature

Dichloro-phosphinic bis-(2-chloro-eth-yl)amide.

Project description:In the title compound, C4H8Cl4NOP, the two chloro-ethyl groups are not related by crystallographic symmetry. The difference in the conformation of the two groups is shown by their N-C-C-Cl torsion angles of 64.57?(15) and 175.62?(10)°.

| S-EPMC3588365 | biostudies-literature

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