(E)-4-Meth­oxy-N′-(4-methyl­benzyl­idene)benzo­hydrazide

Maheswari, R.; Manjula, J.; Gunasekaran, B.

doi:10.1107/S2414314616004314

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 3| March 2016| x160431

doi:10.1107/S2414314616004314

Open

access

(E)-4-Methoxy-N′-(4-methylbenzylidene)benzohydrazide

R. Maheswari,^a J. Manjula ^b ^* and B. Gunasekaran ^c

^aDepartment of Chemistry, Saranathan College of Engineering, Tiruchirappalli, Tamilnadu, India, ^bPG and Research Department of Chemistry, Periyar EVR College, Tiruchirappalli, Tamilnadu, India, and ^cDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai-603 203 Tamil Nadu, India
^*Correspondence e-mail: swaroopapranav@gmail.com, phdguna@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 5 March 2016; accepted 14 March 2016; online 18 March 2016)

In the title compound, C₁₆H₁₆N₂O₂, the dihedral angle between the methoxyphenyl ring and the methylbenzylidene ring is 60.43 (5)°. In the crystal, molecules are linked via N—H⋯O hydrogen bonds, reinforced by C—H⋯O hydrogen bonds, forming chains propagating along the c-axis direction. Inversion-related chains are linked via C—H⋯π interactions, forming ribbons propagating along the c-axis direction.

Keywords: crystal structure; hydrazide; benzohydrazide; N—H⋯O hydrogen bonding..

CCDC reference: 1465282

3D view (loading...)

Chemical scheme

Structure description

Hydrazones have attracted interest due to their versatile applications in various fields, such as biology (Ibrahim et al., 2016 ), medicine (Velezheva et al., 2016 ) and catalysis (Selvamurugan et al., 2016 ). Hydrazone derivatives exhibit antimicrobial (Pieczonka et al., 2013 ), anti-proliferation (Yadagiri et al., 2014 ) and antiplatelet (Mashayekhi et al., 2013 ) activities.

The geometric parameters of the title molecule (Fig. 1) agree well with those reported for similar structures (Maheswari et al., 2016 ; Nair et al., 2012 ). The dihedral angle between the methoxyphenyl ring and the methylbenzylidene ring is 60.43 (5)°.

Figure 1
The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

The crystal packing is controlled by N—H⋯O and C—H⋯O hydrogen bonds (Fig. 2 and Table 1), which result in the formation of chains along [001]. Inversion-related chains are linked via C—H⋯π interactions, forming ribbons propagating along [001].

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.86	2.09	2.9280 (12)	164
C6—H6⋯O2ⁱ	0.93	2.58	3.3093 (14)	136
C9—H9⋯O2ⁱ	0.93	2.50	3.3051 (15)	145
C1—H1C⋯Cg1ⁱⁱ	0.96	2.77	3.6515 (5)	152
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+2, -y+1, -z+1.

Figure 2
The crystal packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines (see Table 1

Synthesis and crystallization

A few drops of conc. HCl were added to a mixture of 4-methoxybenzohydrazide (1.7 g, 0.01 mol) and p-methyl benzaldehyde (1.2 ml, 0.01 mol) in ethanol (15 ml). The reaction mixture was refluxed for 3 h. The precipitate that formed was filtered and washed with petroleum ether and dried in a vacuum desiccator. The crude solid was recrystallized from DMSO giving colourless block-like crystals (yield 96%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O₂
M_r	268.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.7678 (7), 13.0072 (7), 9.9025 (6)
β (°)	112.371 (2)
V (Å³)	1401.66 (14)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.15 × 0.13 × 0.11

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996 )
T_min, T_max	0.987, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	13430, 3517, 2752
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.136, 1.00
No. of reflections	3517
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.18
Computer programs: APEX2 (Bruker, 2008 ), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008 ), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1465282

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616004314/su4020sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616004314/su4020Isup2.hkl

checkCIF report

Experimental top

A few drops of conc. HCl were added to a mixture of 4-methoxybenzohydrazide (1.7 g, 0.01 mol) and p-methyl benzaldehyde (1.2 ml, 0.01 mol) in ethanol (xx ml) how much??. The reaction mixture was refluxed for 3 h. The precipitate that formed was filtered and washed with petroleum ether and dried in a vacuum desiccator. The crude solid was recrystallized from DMSO giving colourless block-like crystals (yield 96%).

Structure description top

Hydrazones have attracted interest due to their versatile applications in various fields, such as biology (Ibrahim et al., 2016), medicine (Velezheva et al., 2016) and catalysis (Selvamurugan et al., 2016). Hydrazone derivatives exhibit antimicrobial (Pieczonka et al., 2013), anti-proliferation (Yadagiri et al., 2014) and antiplatelet (Mashayekhi et al., 2013) activities.

The geometric parameters of the title molecule (Fig. 1) agree well with those reported for similar structures (Maheswari et al., 2016; Nair et al., 2012). The dihedral angle between the methoxyphenyl ring and the methylbenzylidene ring is 60.43 (5)°.

The crystal packing is controlled by N—H···O and C—H···O hydrogen bonds (Fig. 2 and Table 1), which result in the formation of chains along [001]. Inversion-related chains are linked via C—H···π interactions, forming ribbons propagating along [001].

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis. Hydrogen bonds are shown as dashed lines (see Table 1).

(E)-4-Methoxy-N'-(4-methylbenzylidene)benzohydrazide top

Crystal data top

C₁₆H₁₆N₂O₂	F(000) = 568
M_r = 268.31	D_x = 1.271 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.7678 (7) Å	Cell parameters from 3517 reflections
b = 13.0072 (7) Å	θ = 1.9–28.4°
c = 9.9025 (6) Å	µ = 0.09 mm⁻¹
β = 112.371 (2)°	T = 296 K
V = 1401.66 (14) Å³	Block, colourless
Z = 4	0.15 × 0.13 × 0.11 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3517 independent reflections
Radiation source: fine-focus sealed tube	2752 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 0 pixels mm^-1	θ_max = 28.4°, θ_min = 1.9°
ω and φ scans	h = −15→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −17→17
T_min = 0.987, T_max = 0.991	l = −13→12
13430 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.136	w = 1/[σ²(F_o²) + (0.0794P)² + 0.199P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
3517 reflections	Δρ_max = 0.21 e Å⁻³
184 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00

Crystal data top

C₁₆H₁₆N₂O₂	V = 1401.66 (14) Å³
M_r = 268.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.7678 (7) Å	µ = 0.09 mm⁻¹
b = 13.0072 (7) Å	T = 296 K
c = 9.9025 (6) Å	0.15 × 0.13 × 0.11 mm
β = 112.371 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3517 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2752 reflections with I > 2σ(I)
T_min = 0.987, T_max = 0.991	R_int = 0.025
13430 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.00	Δρ_max = 0.21 e Å⁻³
3517 reflections	Δρ_min = −0.18 e Å⁻³
184 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C16	0.5536 (2)	0.86088 (13)	0.1367 (3)	0.0842 (6)
H16A	0.6252	0.9031	0.1805	0.126*
H16B	0.5046	0.8633	0.1952	0.126*
H16C	0.5062	0.8858	0.0404	0.126*
O2	0.76856 (10)	0.20548 (7)	0.35951 (9)	0.0538 (3)
N2	0.70263 (10)	0.37061 (7)	0.17516 (11)	0.0427 (3)
C8	0.77468 (11)	0.19967 (8)	0.23869 (12)	0.0385 (3)
C5	0.82056 (11)	0.10506 (8)	0.19119 (11)	0.0376 (3)
N1	0.74327 (10)	0.27769 (7)	0.14161 (10)	0.0431 (3)
H1	0.7485	0.2697	0.0580	0.052*
C6	0.79284 (11)	0.07902 (9)	0.04612 (12)	0.0401 (3)
H6	0.7425	0.1221	−0.0273	0.048*
O1	0.96488 (10)	−0.16261 (7)	0.09212 (12)	0.0629 (3)
C7	0.83872 (12)	−0.00995 (9)	0.00857 (13)	0.0440 (3)
H7	0.8183	−0.0267	−0.0892	0.053*
C2	0.91488 (12)	−0.07376 (9)	0.11683 (14)	0.0451 (3)
C4	0.89715 (14)	0.03958 (10)	0.29838 (13)	0.0517 (3)
H4	0.9164	0.0553	0.3962	0.062*
C9	0.70520 (12)	0.44398 (9)	0.09164 (13)	0.0446 (3)
H9	0.7339	0.4308	0.0179	0.054*
C10	0.66494 (11)	0.54833 (9)	0.10661 (12)	0.0423 (3)
C3	0.94501 (15)	−0.04806 (10)	0.26235 (14)	0.0559 (4)
H3	0.9975	−0.0900	0.3356	0.067*
C13	0.59258 (13)	0.75127 (10)	0.12739 (16)	0.0541 (3)
C11	0.58724 (12)	0.57071 (10)	0.17829 (15)	0.0482 (3)
H11	0.5589	0.5179	0.2207	0.058*
C12	0.55146 (13)	0.67065 (11)	0.18738 (18)	0.0561 (4)
H12	0.4985	0.6840	0.2350	0.067*
C1	0.93554 (16)	−0.19275 (12)	−0.0552 (2)	0.0667 (4)
H1A	0.8487	−0.2048	−0.1015	0.100*
H1B	0.9792	−0.2547	−0.0576	0.100*
H1C	0.9589	−0.1392	−0.1062	0.100*
C15	0.70586 (16)	0.62896 (11)	0.04561 (18)	0.0595 (4)
H15	0.7576	0.6156	−0.0036	0.071*
C14	0.67073 (16)	0.72906 (11)	0.05695 (19)	0.0636 (4)
H14	0.7002	0.7822	0.0165	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C16	0.0873 (12)	0.0478 (9)	0.1117 (16)	0.0202 (8)	0.0314 (11)	−0.0069 (9)
O2	0.0900 (7)	0.0450 (5)	0.0398 (5)	−0.0012 (4)	0.0399 (5)	−0.0007 (4)
N2	0.0585 (6)	0.0357 (5)	0.0368 (5)	0.0042 (4)	0.0215 (4)	−0.0034 (4)
C8	0.0520 (6)	0.0355 (6)	0.0326 (5)	−0.0045 (5)	0.0213 (5)	−0.0017 (4)
C5	0.0510 (6)	0.0325 (5)	0.0322 (5)	−0.0032 (4)	0.0192 (5)	0.0006 (4)
N1	0.0666 (6)	0.0358 (5)	0.0329 (5)	0.0059 (4)	0.0258 (4)	−0.0008 (4)
C6	0.0505 (6)	0.0366 (6)	0.0323 (5)	0.0033 (5)	0.0145 (5)	0.0014 (4)
O1	0.0764 (7)	0.0416 (5)	0.0668 (7)	0.0149 (5)	0.0228 (5)	−0.0052 (4)
C7	0.0552 (7)	0.0401 (6)	0.0354 (6)	0.0009 (5)	0.0159 (5)	−0.0056 (4)
C2	0.0537 (7)	0.0322 (6)	0.0495 (7)	0.0008 (5)	0.0197 (5)	−0.0010 (5)
C4	0.0775 (9)	0.0442 (7)	0.0309 (6)	0.0032 (6)	0.0176 (6)	0.0032 (5)
C9	0.0617 (7)	0.0391 (6)	0.0381 (6)	0.0040 (5)	0.0245 (5)	−0.0016 (5)
C10	0.0526 (7)	0.0369 (6)	0.0370 (6)	0.0030 (5)	0.0165 (5)	−0.0019 (4)
C3	0.0772 (9)	0.0417 (7)	0.0410 (7)	0.0117 (6)	0.0137 (6)	0.0095 (5)
C13	0.0533 (7)	0.0416 (7)	0.0604 (8)	0.0082 (5)	0.0137 (6)	−0.0043 (6)
C11	0.0495 (7)	0.0439 (7)	0.0546 (7)	−0.0022 (5)	0.0235 (6)	−0.0017 (5)
C12	0.0500 (7)	0.0554 (8)	0.0678 (9)	0.0057 (6)	0.0278 (7)	−0.0081 (6)
C1	0.0732 (10)	0.0504 (8)	0.0802 (11)	0.0034 (7)	0.0333 (8)	−0.0223 (7)
C15	0.0824 (10)	0.0452 (7)	0.0675 (9)	0.0082 (7)	0.0470 (8)	0.0068 (6)
C14	0.0824 (10)	0.0398 (7)	0.0774 (10)	0.0039 (7)	0.0401 (9)	0.0076 (7)

Geometric parameters (Å, º) top

C16—C13	1.5113 (19)	C4—C3	1.3772 (19)
C16—H16A	0.9600	C4—H4	0.9300
C16—H16B	0.9600	C9—C10	1.4636 (16)
C16—H16C	0.9600	C9—H9	0.9300
O2—C8	1.2279 (14)	C10—C15	1.3849 (18)
N2—C9	1.2707 (15)	C10—C11	1.3851 (18)
N2—N1	1.3860 (13)	C3—H3	0.9300
C8—N1	1.3491 (14)	C13—C14	1.380 (2)
C8—C5	1.4901 (15)	C13—C12	1.380 (2)
C5—C6	1.3886 (15)	C11—C12	1.3799 (18)
C5—C4	1.3914 (17)	C11—H11	0.9300
N1—H1	0.8600	C12—H12	0.9300
C6—C7	1.3864 (16)	C1—H1A	0.9600
C6—H6	0.9300	C1—H1B	0.9600
O1—C2	1.3606 (15)	C1—H1C	0.9600
O1—C1	1.421 (2)	C15—C14	1.384 (2)
C7—C2	1.3820 (17)	C15—H15	0.9300
C7—H7	0.9300	C14—H14	0.9300
C2—C3	1.3875 (19)

C13—C16—H16A	109.5	N2—C9—H9	118.6
C13—C16—H16B	109.5	C10—C9—H9	118.6
H16A—C16—H16B	109.5	C15—C10—C11	118.12 (12)
C13—C16—H16C	109.5	C15—C10—C9	118.58 (12)
H16A—C16—H16C	109.5	C11—C10—C9	123.30 (11)
H16B—C16—H16C	109.5	C4—C3—C2	120.03 (12)
C9—N2—N1	113.77 (10)	C4—C3—H3	120.0
O2—C8—N1	123.11 (11)	C2—C3—H3	120.0
O2—C8—C5	121.40 (10)	C14—C13—C12	117.95 (12)
N1—C8—C5	115.48 (9)	C14—C13—C16	120.30 (15)
C6—C5—C4	117.96 (11)	C12—C13—C16	121.75 (15)
C6—C5—C8	123.87 (10)	C12—C11—C10	120.58 (13)
C4—C5—C8	118.17 (10)	C12—C11—H11	119.7
C8—N1—N2	120.74 (9)	C10—C11—H11	119.7
C8—N1—H1	119.6	C11—C12—C13	121.47 (13)
N2—N1—H1	119.6	C11—C12—H12	119.3
C7—C6—C5	121.26 (10)	C13—C12—H12	119.3
C7—C6—H6	119.4	O1—C1—H1A	109.5
C5—C6—H6	119.4	O1—C1—H1B	109.5
C2—O1—C1	117.80 (11)	H1A—C1—H1B	109.5
C2—C7—C6	119.81 (11)	O1—C1—H1C	109.5
C2—C7—H7	120.1	H1A—C1—H1C	109.5
C6—C7—H7	120.1	H1B—C1—H1C	109.5
O1—C2—C7	124.60 (12)	C14—C15—C10	120.86 (14)
O1—C2—C3	115.75 (11)	C14—C15—H15	119.6
C7—C2—C3	119.66 (11)	C10—C15—H15	119.6
C3—C4—C5	121.27 (11)	C13—C14—C15	121.01 (14)
C3—C4—H4	119.4	C13—C14—H14	119.5
C5—C4—H4	119.4	C15—C14—H14	119.5
N2—C9—C10	122.80 (11)

O2—C8—C5—C6	157.52 (12)	N1—N2—C9—C10	179.27 (11)
N1—C8—C5—C6	−23.71 (17)	N2—C9—C10—C15	159.59 (14)
O2—C8—C5—C4	−23.46 (17)	N2—C9—C10—C11	−20.7 (2)
N1—C8—C5—C4	155.32 (12)	C5—C4—C3—C2	−1.5 (2)
O2—C8—N1—N2	0.57 (19)	O1—C2—C3—C4	−178.89 (13)
C5—C8—N1—N2	−178.18 (10)	C7—C2—C3—C4	1.3 (2)
C9—N2—N1—C8	163.64 (12)	C15—C10—C11—C12	0.4 (2)
C4—C5—C6—C7	0.69 (18)	C9—C10—C11—C12	−179.28 (12)
C8—C5—C6—C7	179.72 (11)	C10—C11—C12—C13	−0.8 (2)
C5—C6—C7—C2	−0.86 (19)	C14—C13—C12—C11	0.3 (2)
C1—O1—C2—C7	−0.9 (2)	C16—C13—C12—C11	179.89 (15)
C1—O1—C2—C3	179.30 (14)	C11—C10—C15—C14	0.5 (2)
C6—C7—C2—O1	−179.95 (12)	C9—C10—C15—C14	−179.86 (14)
C6—C7—C2—C3	−0.1 (2)	C12—C13—C14—C15	0.6 (2)
C6—C5—C4—C3	0.5 (2)	C16—C13—C14—C15	−179.04 (16)
C8—C5—C4—C3	−178.61 (13)	C10—C15—C14—C13	−1.0 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	2.09	2.9280 (12)	164
C6—H6···O2ⁱ	0.93	2.58	3.3093 (14)	136
C9—H9···O2ⁱ	0.93	2.50	3.3051 (15)	145
C1—H1C···Cg1ⁱⁱ	0.96	2.77	3.6515 (5)	152

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	2.09	2.9280 (12)	164
C6—H6···O2ⁱ	0.93	2.58	3.3093 (14)	136
C9—H9···O2ⁱ	0.93	2.50	3.3051 (15)	145
C1—H1C···Cg1ⁱⁱ	0.96	2.77	3.6515 (5)	152

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O₂
M_r	268.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.7678 (7), 13.0072 (7), 9.9025 (6)
β (°)	112.371 (2)
V (Å³)	1401.66 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.15 × 0.13 × 0.11

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.987, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	13430, 3517, 2752
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.136, 1.00
No. of reflections	3517
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.18

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Acknowledgements

The authors are grateful to the authorities of Saranathan College of Engineering, Tiruchirappalli, for providing laboratory facilities, and the CAS in Crystallography and Biophysics, University of Madras, Chennai, for the data collection.

References

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ibrahim, H. S., Abou-seri, S. M., Ismail, N. S. M., Elaasser, M. M., Aly, M. H. & Abdel-Aziz, H. A. (2016). Eur. J. Med. Chem. 108, 415–422. CrossRef CAS PubMed Google Scholar
Maheswari, R., Manjula, J. & Gunasekaran, B. (2016). IUCrData, 1, x160304. Google Scholar
Mashayekhi, V., Haj Mohammad Ebrahim Tehrani, K., Amidi, S. & Kobarfard, F. (2013). Chem. Pharm. Bull. 61, 144–150. CrossRef CAS PubMed Google Scholar
Nair, Y., Sithambaresan, M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o2709. CSD CrossRef IUCr Journals Google Scholar
Pieczonka, A. M., Strzelczyk, A., Sadowska, B., Mlostoń, G. & Stączek, P. (2013). Eur. J. Med. Chem. 64, 389–395. Web of Science CrossRef CAS PubMed Google Scholar
Selvamurugan, S., Ramachandran, R., Prakash, G., Viswanathamurthi, P., Malecki, J. G. & Endo, A. (2016). J. Organomet. Chem. 803, 119–127. CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Velezheva, V., Brennan, P., Ivanov, P., Kornienko, A., Lyubimov, S., Kazarian, K., Nikonenko, B., Majorov, K. & Apt, A. (2016). Bioorg. Med. Chem. Lett. 26, 978–985. CrossRef CAS PubMed Google Scholar
Yadagiri, B., Holagunda, U. D., Bantu, R., Nagarapu, L., Guguloth, V., Polepally, S. & Jain, N. (2014). Bioorg. Med. Chem. Lett. 24, 5041–5044. Web of Science CrossRef CAS PubMed Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 3| March 2016| x160431

doi:10.1107/S2414314616004314

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-4-Meth­­oxy-N′-(4-methyl­benzyl­­idene)benzo­hydrazide

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

(E)-4-Methoxy-N′-(4-methylbenzylidene)benzohydrazide