(Z)-N′-[(E)-4-Methoxybenzylidene]-2-(methoxyimino)-2-{2-[(2-methylphenoxy)methyl]phenyl}acetohydrazide

The title compound crystallizes with two molecules in the asymmetric unit. In the crystal, asymmetric, bifurcated N—H⋯(N,O) hydrogen bonds link the molecules into [100] chains. The packing is consolidated by weak C—H⋯O interactions.

The title compound, C 25 H 25 N 3 O 4 , crystallizes with two molecules in the asymmetric unit. In both molecules, the central ethane hydrazide moiety is almost planar. In the crystal, asymmetric, bifurcated N-HÁ Á Á(N,O) hydrogen bonds link the molecules into [100] chains. The packing is consolidated by weak C-HÁ Á ÁO interactions.

Structure description
Kresoxim-methyl derivatives (Cao et al., 2017) are broad-spectrum fungicides (e.g., Grossmann & Retzlaff, 1997), have a site-specific action (Olaya et al., 1998) and high efficiency (Patel et al., 2012) against various diseases of agricultural crops (Balba, 2007). As these types of compounds are easily metabolized in nature as well as in living systems, their modifications are of importance in order to improve their activity (Balba, 2007). In order to increase the activity of the starting compounds (Kant et al. 2012), it is necessary to modify the basic skeleton and initiate a structural investigation of different derivatives of kresoxim-methyl derivatives and in that light we previously reported the crystal structure of a related derivative, (2E)-2-methoxyimino-2-{2-[(2-methylphenoxy)methyl]phenyl}-N 0 -(4-nitrobenzylidene)ethanohydrazide (Shripanavar & Butcher, 2015). This paper is a continuation in this series.
The title compound crystallizes with two molecules, A and B, in the asymmetric unit, as shown in Fig. 1. Both molecules exhibit similar conformations. For molecule A, the central ethane hydrazide moiety N2A/N3A/C17A/O3A is close to planar with an r.m.s. deviation of 0.02 Å for the fitted atoms. The dihedral angles between these atoms and the adjacent rings are 17.1 (2) (C19A methoxyphenyl ring) and 79.9 (2) (C14A benzene data reports ring). This latter ring and the C1A toluyl ring are almost perpendicular, with a dihedral angle of 82.1 (1) For molecule B, the central ethane hydrazide moiety N2B/ N3B/C17B/O3B is also close to planar, with an r.m.s. deviation of 0.01 Å for the fitted atoms. The equivalent dihedral angles to those in molecule A are 13.3 (2), 80.5 (2) and 86.1 (1) , respectively.
In the crystal, bifurcated, asymmetric N-HÁ Á Á(N,O) hydrogen bonds (Table 1) link alternating A and B molecules into a zigzag chain propagating in the a-axis direction, as shown in Fig. 2. It is of interest that the shorter bond is to an O atom in one of these links and to an N atom in the other. The packing is consolidated by weak C-HÁ Á ÁO interactions.
A search for related structures resulted in two close matches. The first is the parent azide from which the current structure is derived (Chopra et al., 2004) and the second is that with a nitro substituent instead of a methoxy substituent on the phenyl ring (CSD refcode JUFCIY; Shripanavar & Butcher, 2015). The major difference between the methoxy and nitro derivatives lies in the dihedral angles between the central benzene rings and the o-tolyl groups at the other end of the molecule: in the current structure these are 82.1 (1) and 86.1 (1) while in JUFCIY the equivalent angles are 46.98 (5) and 48.23 (4) .

Figure 1
The molecular structure of the two independent molecules of the title compound with hydrogen bonds shown as dashed lines. Atomic displacement parameters are at the 30% probability level.
where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.24 e Å −3 Δρ min = −0.28 e Å −3 Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

data-2
IUCrData (2020). 5, x201060 Refinement. H atoms were positioned geometrically and refined as riding: C-H = 0.95-0.98 Å with U iso (H) = 1.5U eq (C) for methyl H atoms and = 1.2U eq (C) for other H atoms. Amine H atoms were refined isotropically. The absolute structure could not be determined in the present refinement.