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(E)-1-(2,4-Dinitro-phen-yl)-2-(2-fluoro-benzyl-idene)hydrazine.

ABSTRACT: In the title compound, C(13)H(9)FN(4)O(4), the dihedral angle between the mean planes of the two benzene rings of the nearly planar mol-ecule is 6.6?(9)°. The dihedral angles between the mean planes of the benzene ring and its two attached nitro groups are 6.7?(7) and 7.2?(9)°. Crystal packing is stabilized by N-H?O hydrogen bonds, weak C-H?O and C-H?F inter-molecular inter-actions and centroid-centroid ?-ring stacking inter-actions.

SUBMITTER: Jasinski JP

PROVIDER: S-EPMC3089184 | biostudies-literature | 2011 May

REPOSITORIES: biostudies-literature

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(E)-1-(2,4-Dinitro-phen-yl)-2-(2-fluoro-benzyl-idene)hydrazine.

Jasinski Jerry P JP Braley Adam N AN Chidan Kumar C S CS Yathirajan H S HS Mayekar A N AN

Acta crystallographica. Section E, Structure reports online 20110422 Pt 5

In the title compound, C(13)H(9)FN(4)O(4), the dihedral angle between the mean planes of the two benzene rings of the nearly planar mol-ecule is 6.6 (9)°. The dihedral angles between the mean planes of the benzene ring and its two attached nitro groups are 6.7 (7) and 7.2 (9)°. Crystal packing is stabilized by N-H⋯O hydrogen bonds, weak C-H⋯O and C-H⋯F inter-molecular inter-actions and centroid-centroid π-ring stacking inter-actions. ...[more]

PMID: 21754502

Similar Datasets

1-(2-Chloro-benzyl-idene)-2-(2,4-dinitro-phen-yl)hydrazine.

Project description:In the title compound, C(13)H(9)ClN(4)O(4), there are two crystallographically independent mol-ecules in the asymmetric unit, which have very similar conformations. The C=N-N angles in each independent mol-ecule are 115.0?(2) and 116.6?(2)°, which are significantly smaller than the ideal value of 120° expected for sp(2)-hybridized N atoms. This is probably a consequence of repulsion between the nitro-gen lone pairs and the adjacent N-N bonds. Two bifurcated intra-molecular N-H?O hydrogen bonds help to establish the mol-ecular conformation and consolidate the crystal packing.

| S-EPMC2959777 | biostudies-literature

(E)-1-(2,4-Dinitro-phen-yl)-2-[1-(4-fluoro-phen-yl)ethyl-idene]hydrazine.

Project description:The title compound, C(14)H(11)FN(4)O(4), crystallizes with two essentially planar mol-ecules in the asymmetric unit; the dihedral angles between the benzene rings are 1.57?(15) and 6.17?(15)°. In each mol-ecule, an intra-molecular N-H?O hydrogen bond generates an S(6) ring. In the crystal, mol-ecules are linked by weak C-H?O and C-H?F inter-actions into sheets lying parallel to (120). O?C [2.980?(4)?Å] and O?N [2.892?(3)?Å] short contacts also occur.

| S-EPMC3275075 | biostudies-literature

1-(2,3-Dimeth-oxy-benzyl-idene)-2-(2,4-dinitro-phen-yl)hydrazine.

Project description:In the title compound, C(15)H(14)N(4)O(6), the dihedral angle between the aromatic rings is 3.7?(4)°. The nitro groups make dihedral angles of 6.0?(4) and 5.2?(4)° with the parent ring and are oriented at 6.0?(6)° with respect to each other. The meth-oxy groups are inclined at 54.0?(2) and 2.5?(3)° with respect to the benzene ring to which they are attached. In the crystal, mol-ecules are linked by weak C-H?O inter-actions. The mol-ecular conformation is consolidated by an intra-molecular N-H?O hydrogen bond.

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N-[1-(Biphenyl-4-yl)ethyl-idene]-N'-(2,4-dinitro-phen-yl)hydrazine.

Project description:The title compound, C(20)H(16)N(4)O(4), contains two crystallographically independent mol-ecules (A and B) in the asymmetric unit. Intra-molecular N-H?O hydrogen bonds generate S(6) ring motifs in both molecules. The dihedral angles between the nitro-substituted benzene rings and the two benzene rings in mol-ecules A and B are 14.32?(9), 17.89?(9)° and 13.04?(9) and 25.71?(9)°. The ortho and para nitro groups form dihedral angles of 6.2?(2) and 8.5?(2)° in mol-ecule A, and 5.3?(3) and 13.8?(2)° in mol-ecule B, with the benzene rings to which they are attached. The crystal structure is stabilized by inter-molecular C-H?O inter-actions.

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(E)-1-[1-(2-Chloro-phen-yl)ethyl-idene]-2-(2,4-dinitro-phen-yl)hydrazine.

Project description:The title mol-ecule, C(14)H(11)ClN(4)O(4), is in an E configuration and is twisted with the dihedral angle between the two benzene rings being 38.48?(8)°. The ethyl-idenehydrazine plane makes dihedral angles of 6.03?(10) and 44.04?(11)°, respectively, with the dinitro- and chloro-substituted benzene rings. The two nitro groups are essentially coplanar with the bound benzene ring, making dihedral angles of 0.9?(2) and 1.65?(18)°. An intra-molecular N-H?O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked by a weak C-H?O inter-action into a chain along the c axis. The chains are further stacked along the b axis by a ?-? inter-action with a centroid-centroid distance of 3.6088?(10)?Å.

| S-EPMC3239123 | biostudies-literature

(E)-1-(2,4-Dinitro-phen-yl)-2-[1-(thio-phen-2-yl)ethyl-idene]hydrazine.

Project description:The mol-ecule of the title compound, C(12)H(10)N(4)O(4)S, is slightly twisted, with a dihedral angle of 8.23?(9)° between the benzene and thio-phene rings. One nitro group is co-planar [O-N-C-C torsion angles = -0.5?(3) and -1.9?(3)°] whereas the other is slightly twisted with respect to the benzene ring [O-N-C-C torsion angles = -5.1?(3) and -5.7?(3)°]. In the crystal, the mol-ecules are linked by weak C-H?O inter-actions into screw chains along the b axis. The mol-ecular conformation is consolidated by an intra-molecular N-H?O hydrogen bond.

| S-EPMC3089201 | biostudies-literature

(E)-1-(2,4-Dinitro-phen-yl)-2-[1-(2-nitro-phen-yl)ethyl-idene]hydrazine.

Project description:The title compound, C(14)H(11)N(5)O(6), was obtained from the condensation reaction of 2,4-dinitro-phenyl-hydrazine and 2-nitro-acetophenone. The mol-ecule displays an E conformation about the C=N double bond and an intra-molecular N-H?O hydrogen bond generates an S(6) ring motif. The dihedral angle between the benzene rings is 7.84?(6)°. In the crystal, mol-ecules are linked by C-H?O hydrogen bonds and ?-? stacking inter-actions [centroid-centroid distance = 3.6447?(8)?Å] into a three-dimensional network.

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(E)-1-(2,4-Dinitro-phen-yl)-2-[1-(3-nitro-phen-yl)ethyl-idene]hydrazine.

Project description:In the asymmetric unit of the title compound, C(14)H(11)N(5)O(6), there are three crystallographically independent mol-ecules with similar conformations but some differences in bond angles. The mol-ecules are slightly twisted with the dihedral angles between the benzene rings being 10.02?(14), 8.41?(15) and 1.40?(14)°. In each mol-ecule, an intra-molecular N-H?O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked by weak C-H?O inter-actions into a three-dimensional network. ?-? inter-actions with centroid-centroid distances of 3.5635?(17)-3.8273?(18)?Å are observed.

| S-EPMC3435706 | biostudies-literature

(1Z)-1-[(2E)-3-(4-Bromo-phen-yl)-1-(4-fluoro-phen-yl)prop-2-en-1-yl-idene]-2-(2,4-dinitro-phen-yl)hydrazine.

Project description:In the title mol-ecule, C(21)H(14)BrFN(4)O(4), the mean planes of the two nitro groups form dihedral angles of 3.1 (2) and 7.1 (5)° with the benzene ring to which they are attached. The dinitro-substituted ring forms dihedral angles of 8.6 (2) and 71.9 (2)° with the bromo- and fluoro-substituted benzene rings, respectively. The dihedral angle between the bromo- and fluoro-substituted benzene rings is 80.6 (2)°. There is an intra-molecular N-H⋯O hydrogen bond. In the crystal, pairs of weak C-H⋯O hydrogen bonds form inversion dimers. In addition, π-π stacking inter-actions between the bromo- and dinitro-substituted rings [centroid-centroid separation = 3.768 (2) Å] are observed.

| S-EPMC3393993 | biostudies-literature

(E)-1-(2,4-Dinitro-phen-yl)-2-[1-(3-fluoro-phen-yl)ethyl-idene]hydrazine.

Project description:The mol-ecule of the title hydrazone derivative, C(14)H(11)FN(4)O(4), is nearly planar, with a dihedral angle between the benzene rings of 3.71?(7)°. The central ethyl-idenehydrazine N-N=C-C plane makes dihedral angles of 5.32?(10) and 9.02?(10)° with the 2,4-dinitro- and 3-fluoro-substituted benzene rings, respectively. An intra-molecular N-H?O bond generates an S(6) ring motif. In the crystal, mol-ecules are linked by weak C-H?O inter-actions into a sheet parallel to (10-1). The mol-ecules are further stacked along the a axis by ?-? inter-actions with centroid-centroid distances of 3.6314?(9) and 3.7567?(10)?Å. A C?F short contact [2.842?(3)?Å] is observed. The 3-fluoro-phenyl group is disordered over two orientations with a site-occupancy ratio of 0.636?(3):0.364?(3).

| S-EPMC3379246 | biostudies-other

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