1,2-Bis(3-phen­oxy­benzyl­idene)hydrazine

Jasinski, J.P.; Golen, J.A.; Praveen, A.S.; Narayana, B.; Yathirajan, H.S.

doi:10.1107/S1600536811052469

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o81

doi:10.1107/S1600536811052469

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1,2-Bis(3-phenoxybenzylidene)hydrazine

Jerry P. Jasinski,^a ^* James A. Golen,^a A. S. Praveen,^b B. Narayana ^c and H. S. Yathirajan ^b

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, 574 199, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 24 November 2011; accepted 5 December 2011; online 10 December 2011)

Molecules of the title compound, C₂₆H₂₀N₂O₂, reside on crystallographic centres of inversion located at the mid-point of the N—N bond. The benzylidene ring is essentially coplanar with the central hydrazine group, with an interplanar angle of 4.5 (2)°, whereas the phenyl ring is oriented at 34.0 (3)° with respect to the mean plane of the central 1,2-dibenzylidenehydrazine group. In the crystal, C—H⋯π(arene)-ring interactions link molecules about inversion centres.

Related literature

For the biological activity of Schiff bases, see: Aydogan et al. (2001 ); Desai et al. (2001 ); El-masry et al. (2000 ); Hodnett & Dunn (1970 ); Kundu et al. (2005 ); Pandeya et al. (1999 ); Singh & Dash (1988 ); Taggi et al. (2002 ); Xu et al. (1997 ); For crystallography and coordination chemistry of compounds containing the azine functionality or a diimine linkage, see: Xu et al. (1997); Kundu et al. (2005); For related structures, see: Liu et al. (2007 ); Odabaşoğlu et al. (2007 ); Zhang & Zheng (2008 ); Zheng et al. (2005a ,b ). For standard bond lengths, see Allen et al. (1987 ).

Experimental

Crystal data

C₂₆H₂₀N₂O₂
M_r = 392.44
Monoclinic, C 2/c
a = 23.6271 (16) Å
b = 11.2942 (6) Å
c = 8.2359 (7) Å
β = 109.538 (8)°
V = 2071.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 170 K
0.44 × 0.20 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.966, T_max = 0.995
4228 measured reflections
2341 independent reflections
1643 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.144
S = 1.05
2341 reflections
136 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C7–C12 benzylidene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯Cgⁱ	0.93	2.68	3.5947 (17)	167
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811052469/gg2067sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811052469/gg2067Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811052469/gg2067Isup3.cml

checkCIF report

Comment top

Schiff bases are known to exhibit biological activity such as antimicrobial (El-masry et al., 2000 & Pandeya et al., 1999), antifungal (Singh & Dash, 1988), antitumor (Hodnett & Dunn, 1970; Desai et al., 2001) and as herbicides. Moreover, Schiff bases are used as substrates in the preparation of number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. Schiff bases have also been employed as ligands for complexation of metal ions (Aydogan et al., 2001). On the industrial scale, they have wide range of applications such as dyes and pigments (Taggi et al., 2002). Compounds containing an azine functionality or a diimine linkage have been investigated in terms of their crystallography and coordination chemistry (Xu et al., 1997; Kundu et al., 2005).

The crystal structures of some Schiff base hydrazines, viz., 4-fluorobenzaldehyde[(E)-4-fluorobenzylidene]hydrazone (Odabaşoğlu et al., 2007), N,N'-bis(3-nitrobenzylidene)hydrazine (Zheng et al., 2005a), N,N'-Bis(4-chlorobenzylidene)hydrazine (Zheng et al., 2005b), 1,2-bis(2-chlorobenzylidene)hydrazine (Zhang & Zheng, 2008), N,N'-Bis(4-hydroxybenzylidene)hydrazine (Liu et al., 2007) have been reported. In view of the importance of Schiff base hydrazines, the crystal structure of title compound (I) is reported herein.

The complete molecule of the title compound, C₂₆H₂₀N₂O₂, is generated by the application of a centre of inversion (Fig. 1). The benzylidene ring is essentially coplanar with the central hydrazine group [dihedral angle = 4.5 (2)°] The dihedral angle between the mean plane of the 1,2-bis(benzylidene) hydrazine group and the two parallel phenyl rings is 34.0 (3)°. Weak C—H···Cg π-ring intermolecular interactions are observed (Table 1) providing some crystal packing stability (Fig. 2).

Related literature top

For the biological activity of Schiff bases, see: Aydogan et al. (2001); Desai et al. (2001); El-masry et al. (2000); Hodnett & Dunn (1970); Kundu et al. (2005) ; Pandeya et al. (1999); Singh & Dash (1988); Taggi et al. (2002); Xu et al. (1997); For crystallography and coordination chemistry of compounds containing the azine functionality or a diimine linkage, see: Xu et al. (1997); Kundu et al. (2005); For related structures, see: Liu et al. (2007); Odabaşoğlu et al. (2007); Zhang & Zheng (2008); Zheng et al. (2005a,b). For standard bond lengths, see Allen et al. (1987).

Experimental top

A mixture of 3-phenoxybenzaldehyde (0.02 mol) and hydrazine hydrate (0.012 mol) was refluxed in 15 ml of absolute alcohol containing 2 drops of sulfuric acid, for about 3 hours. On cooling, the resulting solid was filtered and dried. Single crystals were grown from DMF (dimethylformamide) by the slow evaporation method. Yield: 86%. (m.p.: 404 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound viewed along the c axis. The H atoms have been removed for clarity.

1,2-Bis(3-phenoxybenzylidene)hydrazine top

Crystal data top

C₂₆H₂₀N₂O₂	F(000) = 824
M_r = 392.44	D_x = 1.259 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1146 reflections
a = 23.6271 (16) Å	θ = 3.1–28.6°
b = 11.2942 (6) Å	µ = 0.08 mm⁻¹
c = 8.2359 (7) Å	T = 170 K
β = 109.538 (8)°	Plate, yellow
V = 2071.2 (3) Å³	0.44 × 0.20 × 0.06 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	2341 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1643 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 16.1500 pixels mm^-1	θ_max = 28.7°, θ_min = 3.1°
ω scans	h = −31→19
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −12→14
T_min = 0.966, T_max = 0.995	l = −10→10
4228 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0591P)² + 0.4457P] where P = (F_o² + 2F_c²)/3
2341 reflections	(Δ/σ)_max < 0.001
136 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₆H₂₀N₂O₂	V = 2071.2 (3) Å³
M_r = 392.44	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 23.6271 (16) Å	µ = 0.08 mm⁻¹
b = 11.2942 (6) Å	T = 170 K
c = 8.2359 (7) Å	0.44 × 0.20 × 0.06 mm
β = 109.538 (8)°

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	2341 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	1643 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.995	R_int = 0.023
4228 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.144	H-atom parameters constrained
S = 1.05	Δρ_max = 0.14 e Å⁻³
2341 reflections	Δρ_min = −0.19 e Å⁻³
136 parameters

Special details top

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
O1	0.28415 (5)	0.56492 (12)	0.14723 (17)	0.0634 (4)
N1	0.02329 (6)	0.53855 (12)	0.04610 (19)	0.0533 (4)
C1	0.36654 (9)	0.54126 (16)	0.4051 (2)	0.0582 (5)
H1B	0.3467	0.4787	0.4361	0.070*
C2	0.42338 (10)	0.5731 (2)	0.5077 (3)	0.0769 (7)
H2A	0.4421	0.5321	0.6096	0.092*
C3	0.45254 (9)	0.6644 (2)	0.4612 (3)	0.0818 (7)
H3A	0.4911	0.6854	0.5310	0.098*
C4	0.42510 (10)	0.7249 (2)	0.3120 (3)	0.0760 (7)
H4A	0.4450	0.7870	0.2802	0.091*
C5	0.36825 (9)	0.69433 (15)	0.2091 (2)	0.0584 (5)
H5A	0.3493	0.7355	0.1076	0.070*
C6	0.33985 (7)	0.60286 (14)	0.2574 (2)	0.0432 (4)
C7	0.23306 (7)	0.60721 (15)	0.1737 (2)	0.0442 (4)
C8	0.23209 (7)	0.70730 (14)	0.2691 (2)	0.0483 (4)
H8A	0.2672	0.7497	0.3218	0.058*
C9	0.17840 (8)	0.74360 (15)	0.2851 (2)	0.0491 (4)
H9A	0.1776	0.8111	0.3491	0.059*
C10	0.12623 (7)	0.68200 (14)	0.2084 (2)	0.0462 (4)
H10A	0.0905	0.7071	0.2213	0.055*
C11	0.12717 (7)	0.58123 (13)	0.1108 (2)	0.0416 (4)
C12	0.18101 (7)	0.54480 (14)	0.0936 (2)	0.0441 (4)
H12A	0.1820	0.4783	0.0281	0.053*
C13	0.07271 (7)	0.51346 (15)	0.0257 (2)	0.0469 (4)
H13A	0.0743	0.4504	−0.0452	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0376 (6)	0.0815 (9)	0.0687 (9)	−0.0038 (6)	0.0148 (6)	−0.0324 (7)
N1	0.0396 (8)	0.0516 (9)	0.0670 (10)	−0.0047 (6)	0.0156 (7)	−0.0052 (7)
C1	0.0663 (12)	0.0553 (11)	0.0548 (11)	−0.0063 (9)	0.0226 (9)	0.0036 (9)
C2	0.0680 (14)	0.0838 (16)	0.0605 (13)	0.0133 (13)	−0.0029 (11)	0.0005 (11)
C3	0.0425 (11)	0.0966 (18)	0.0949 (18)	−0.0106 (12)	0.0079 (11)	−0.0309 (15)
C4	0.0707 (14)	0.0690 (14)	0.0975 (18)	−0.0299 (12)	0.0403 (14)	−0.0178 (13)
C5	0.0670 (12)	0.0496 (10)	0.0595 (11)	−0.0038 (9)	0.0225 (10)	0.0045 (9)
C6	0.0354 (8)	0.0473 (9)	0.0479 (9)	−0.0026 (7)	0.0152 (7)	−0.0100 (7)
C7	0.0383 (8)	0.0501 (9)	0.0433 (9)	0.0021 (7)	0.0123 (7)	−0.0041 (7)
C8	0.0431 (9)	0.0499 (10)	0.0466 (9)	−0.0039 (8)	0.0080 (7)	−0.0081 (8)
C9	0.0516 (10)	0.0447 (9)	0.0482 (10)	0.0061 (8)	0.0131 (8)	−0.0054 (8)
C10	0.0434 (9)	0.0477 (9)	0.0479 (9)	0.0082 (7)	0.0157 (7)	0.0030 (7)
C11	0.0407 (8)	0.0412 (9)	0.0425 (9)	0.0005 (7)	0.0134 (7)	0.0047 (7)
C12	0.0423 (9)	0.0431 (9)	0.0459 (9)	−0.0014 (7)	0.0133 (7)	−0.0063 (7)
C13	0.0436 (9)	0.0453 (9)	0.0527 (10)	−0.0013 (7)	0.0175 (8)	−0.0007 (8)

Geometric parameters (Å, º) top

O1—C7	1.3814 (18)	C5—H5A	0.9300
O1—C6	1.3930 (18)	C7—C12	1.379 (2)
N1—C13	1.266 (2)	C7—C8	1.381 (2)
N1—N1ⁱ	1.410 (3)	C8—C9	1.381 (2)
C1—C6	1.359 (2)	C8—H8A	0.9300
C1—C2	1.374 (3)	C9—C10	1.372 (2)
C1—H1B	0.9300	C9—H9A	0.9300
C2—C3	1.364 (3)	C10—C11	1.398 (2)
C2—H2A	0.9300	C10—H10A	0.9300
C3—C4	1.365 (3)	C11—C12	1.388 (2)
C3—H3A	0.9300	C11—C13	1.459 (2)
C4—C5	1.371 (3)	C12—H12A	0.9300
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.362 (2)

C7—O1—C6	118.43 (12)	C12—C7—O1	115.75 (14)
C13—N1—N1ⁱ	112.25 (17)	C8—C7—O1	123.66 (14)
C6—C1—C2	118.82 (18)	C9—C8—C7	119.21 (15)
C6—C1—H1B	120.6	C9—C8—H8A	120.4
C2—C1—H1B	120.6	C7—C8—H8A	120.4
C3—C2—C1	120.4 (2)	C10—C9—C8	121.21 (15)
C3—C2—H2A	119.8	C10—C9—H9A	119.4
C1—C2—H2A	119.8	C8—C9—H9A	119.4
C2—C3—C4	119.92 (19)	C9—C10—C11	119.53 (15)
C2—C3—H3A	120.0	C9—C10—H10A	120.2
C4—C3—H3A	120.0	C11—C10—H10A	120.2
C3—C4—C5	120.2 (2)	C12—C11—C10	119.42 (14)
C3—C4—H4A	119.9	C12—C11—C13	119.11 (14)
C5—C4—H4A	119.9	C10—C11—C13	121.47 (14)
C6—C5—C4	119.14 (19)	C7—C12—C11	120.06 (15)
C6—C5—H5A	120.4	C7—C12—H12A	120.0
C4—C5—H5A	120.4	C11—C12—H12A	120.0
C1—C6—C5	121.55 (17)	N1—C13—C11	121.53 (15)
C1—C6—O1	118.67 (15)	N1—C13—H13A	119.2
C5—C6—O1	119.58 (16)	C11—C13—H13A	119.2
C12—C7—C8	120.56 (15)

C6—C1—C2—C3	−0.5 (3)	O1—C7—C8—C9	178.76 (16)
C1—C2—C3—C4	0.2 (3)	C7—C8—C9—C10	0.1 (3)
C2—C3—C4—C5	0.1 (3)	C8—C9—C10—C11	−0.6 (2)
C3—C4—C5—C6	−0.2 (3)	C9—C10—C11—C12	0.3 (2)
C2—C1—C6—C5	0.4 (3)	C9—C10—C11—C13	−179.48 (15)
C2—C1—C6—O1	175.27 (16)	C8—C7—C12—C11	−1.1 (3)
C4—C5—C6—C1	0.0 (3)	O1—C7—C12—C11	−179.24 (14)
C4—C5—C6—O1	−174.87 (16)	C10—C11—C12—C7	0.5 (2)
C7—O1—C6—C1	88.2 (2)	C13—C11—C12—C7	−179.68 (14)
C7—O1—C6—C5	−96.80 (19)	N1ⁱ—N1—C13—C11	−179.40 (15)
C6—O1—C7—C12	−163.42 (14)	C12—C11—C13—N1	175.49 (16)
C6—O1—C7—C8	18.5 (2)	C10—C11—C13—N1	−4.7 (3)
C12—C7—C8—C9	0.7 (3)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C7–C12 benzylidene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···Cgⁱⁱ	0.93	2.68	3.5947 (17)	167

Symmetry code: (ii) −x+1/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₀N₂O₂
M_r	392.44
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	170
a, b, c (Å)	23.6271 (16), 11.2942 (6), 8.2359 (7)
β (°)	109.538 (8)
V (Å³)	2071.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.44 × 0.20 × 0.06

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.966, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	4228, 2341, 1643
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.675

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.144, 1.05
No. of reflections	2341
No. of parameters	136
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.19

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C7–C12 benzylidene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···Cgⁱ	0.93	2.68	3.5947 (17)	167

Symmetry code: (i) −x+1/2, −y+1/2, −z.

Acknowledgements

ASP thanks the University of Mysore for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o81

doi:10.1107/S1600536811052469

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