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N ′ -[1-(5-Bromo-2-hy ­ droxy ­ phen ­ yl)ethyl ­ idene]isonicotinohydrazide monohydrate: crystal structure and Hirshfeld surface analysis

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ABSTRACT

In the title isonicotinohydrazide hydrate, C14H12BrN3O2·H2O {systematic name: N′-[(1E)-1-(5-bromo-2-hy­droxy­phen­yl)ethyl­idene]pyridine-4-carbohydrazide monohydrate}, the central CN2O region of the organic mol­ecule is planar and the conformation about the imine-C=N bond is E. While an intra­molecular hy­droxy-O—H⋯N(imine) hydrogen bond is evident, the dihedral angle between the central residue and the benzene rings is 48.99 (9)°. Overall, the mol­ecule is twisted, as seen in the dihedral angle of 71.79 (6)° between the outer rings. In the crystal, hydrogen-bonding inter­actions, i.e. hydrazide-N—H⋯O(water), water-O—H⋯O(carbon­yl) and water-O—H⋯N(pyrid­yl), lead to supra­molecular ribbons along the a-axis direction. Connections between these, leading to a three-dimensional architecture, are mediated by Br⋯Br halogen bonding [3.5366 (3) Å], pyridyl-C—H⋯O(carbon­yl) as well as weak π–π inter­actions [inter-centroid separation between benzene rings = 3.9315 (12) Å]. The Hirshfeld surface analysis reveals the importance of hydrogen atoms in the supra­molecular connectivity as well as the influence of the Br⋯Br halogen bonding.

No MeSH data available.


The mol­ecular structures of constituents of (I) showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.
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fig1: The mol­ecular structures of constituents of (I) showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.

Mentions: The mol­ecular structures of the constituents of (I) are shown in Fig. 1 ▸. The organic mol­ecule features a central, essentially planar region flanked on either side by a pyridyl ring and a di-substituted benzene ring. The central residue comprising the N1, N2, O1 and C1 atoms is strictly planar [r.m.s. deviation of the fitted atoms = 0.0001 Å] with the C2 and C10 atoms lying 0.171 (3) and 0.010 (4) Å, respectively, out of the plane; the carbonyl-O and hydrazide-NH groups are anti. The sequence of N1—N2—C2—C3 [−177.59 (15)°], N2—N1—C1—C10 [179.59 (15)°] and C1—N1—N2—C2 [171.14 (18)°] torsion angles is consistent with an all-trans relationship in the central chain and a small twist about the N1—N2 bond. The conformation about the imine-C2=N2 bond [1.292 (2) Å] is E. An intra­molecular hy­droxy-O1—H⋯N2(imine) hydrogen bond is noted, Table 1 ▸. The dihedral angles between the central residue and the pyridyl and benzene rings are 23.16 (10) and 48.99 (9)°, respectively. As the six-membered rings are con-rotatory with respect to the chain, the dihedral angle between them of 71.79 (6)° indicates an approximately orthogonal relationship.


N ′ -[1-(5-Bromo-2-hy ­ droxy ­ phen ­ yl)ethyl ­ idene]isonicotinohydrazide monohydrate: crystal structure and Hirshfeld surface analysis
The mol­ecular structures of constituents of (I) showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5382638&req=5

fig1: The mol­ecular structures of constituents of (I) showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.
Mentions: The mol­ecular structures of the constituents of (I) are shown in Fig. 1 ▸. The organic mol­ecule features a central, essentially planar region flanked on either side by a pyridyl ring and a di-substituted benzene ring. The central residue comprising the N1, N2, O1 and C1 atoms is strictly planar [r.m.s. deviation of the fitted atoms = 0.0001 Å] with the C2 and C10 atoms lying 0.171 (3) and 0.010 (4) Å, respectively, out of the plane; the carbonyl-O and hydrazide-NH groups are anti. The sequence of N1—N2—C2—C3 [−177.59 (15)°], N2—N1—C1—C10 [179.59 (15)°] and C1—N1—N2—C2 [171.14 (18)°] torsion angles is consistent with an all-trans relationship in the central chain and a small twist about the N1—N2 bond. The conformation about the imine-C2=N2 bond [1.292 (2) Å] is E. An intra­molecular hy­droxy-O1—H⋯N2(imine) hydrogen bond is noted, Table 1 ▸. The dihedral angles between the central residue and the pyridyl and benzene rings are 23.16 (10) and 48.99 (9)°, respectively. As the six-membered rings are con-rotatory with respect to the chain, the dihedral angle between them of 71.79 (6)° indicates an approximately orthogonal relationship.

View Article: PubMed Central - HTML - PubMed

ABSTRACT

In the title isonicotinohydrazide hydrate, C14H12BrN3O2·H2O {systematic name: N′-[(1E)-1-(5-bromo-2-hy­droxy­phen­yl)ethyl­idene]pyridine-4-carbohydrazide monohydrate}, the central CN2O region of the organic mol­ecule is planar and the conformation about the imine-C=N bond is E. While an intra­molecular hy­droxy-O—H⋯N(imine) hydrogen bond is evident, the dihedral angle between the central residue and the benzene rings is 48.99 (9)°. Overall, the mol­ecule is twisted, as seen in the dihedral angle of 71.79 (6)° between the outer rings. In the crystal, hydrogen-bonding inter­actions, i.e. hydrazide-N—H⋯O(water), water-O—H⋯O(carbon­yl) and water-O—H⋯N(pyrid­yl), lead to supra­molecular ribbons along the a-axis direction. Connections between these, leading to a three-dimensional architecture, are mediated by Br⋯Br halogen bonding [3.5366 (3) Å], pyridyl-C—H⋯O(carbon­yl) as well as weak π–π inter­actions [inter-centroid separation between benzene rings = 3.9315 (12) Å]. The Hirshfeld surface analysis reveals the importance of hydrogen atoms in the supra­molecular connectivity as well as the influence of the Br⋯Br halogen bonding.

No MeSH data available.