Crystal structure of 4-chloro- N ′ -[(1 E )-(2-nitrophenyl)methylidene]benzohydrazide, C 14 H 10 ClN 3 O 3

C 14 H 10 ClN 3 O 3 , triclinic, P 1 (no. 1), a = 4.8813(2) Å, b = 6.7806(2) Å, c = 10.3135(2) Å, α = 98 . 101 ( 2 ) ∘ , β = 94 . 174 ( 2 ) ∘ , γ = 97 . 612 ( 3 ) ∘ , V = 333.515(18) Å 3 , Z = 1, R gt (F) = 0.0270, wR ref (F 2 ) = 0.0743, T = 160 K.


Experimental details
The C-bound H atoms were geometrically placed (C-H = 0.95 Å) and refined as riding with U iso (H) = 1.2U eq (C). The N-bound H atoms were located in a difference map and refined with N-H = 0.88 ± 0.01 and with U iso (H) = 1.2U eq (N).

Comment
Nʹ-Arylidene hydrazide derivatives have been utilised as important starting materials in the synthesis of various heterocyclic compounds having diverse biological activities [5][6][7][8]. Herein, the crystal and molecular structures of the title Nʹ-arylidene hydrazide derivative, (I), are described, complemented with an analysis of the calculated Hirshfeld surfaces and a comparison with the isomorphous bromo derivative [9]. The molecular structure of (I) is shown in the figure (50% probability ellipsoids). The central residue, comprising the C1, C2, N1, N2 and O1 atoms is close to planar, exhibiting an r.m.s. deviation of 0.0180 Å; the maximum deviations from the least-squares plane through these atoms are C1 [0.0237(14) Å] and N1 [0.0247(14) Å] atoms which lie to opposite sides of the plane. Each of the attached chlorophenyl and nitrophenyl rings is rotated out of the plane through the central residue, forming dihedral angles of 32.54 (11) and 36.61(11) ∘ , respectively. A disrotatory relationship exists between the phenyl rings as indicated by the dihedral angle between them of 4.08(15) ∘ . The nitro group is twisted out of the plane through the ring to which it is connected, forming a dihedral angle of 20.9( 3) ∘ . The constituent atoms of the amide group adopt an transconformation, and the configuration about the C2=N2 imine bond [1.

279(3) Å] is E.
In the crystallographic literature, there is the isostructural bromo derivative [9], (II), along with the parent nitro compound [10], (III), available for comparison; the parent nitro compound is not a hydrate as indicated in the title of the publication [10]. An overlay diagram (not shown) of (I)-(III) shows (I) and (II) to be virtually superimposable. However, minor differences are evident for (III), most notably in the opposite orientation of the nitro group; the dihedral angles between the outer rings in (II) and (III) are 4.13(9) and 1.45(8) ∘ , respectively, cf. 4.08(15) ∘ for (I).
In An analysis of the calculated Hirshfeld surfaces for (I) and isostructural (II) were also conducted employing CrystalExplorer [11] following literature precedents [12]. This analysis on the packing in the crystal of (I) indicates a wide range of significant surface contacts with 83.5 % of these involving hydrogen. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

Atom
x y z U iso */U eq