1,2-Bis[(2-hydr­oxy-3-methoxy­benzyl­idene)hydrazono]-1,2-diphenyl­ethane

Zhang, X.-Y.; Ma, H.; Chang, J.-L.; Wu, X.-C.

doi:10.1107/S1600536808014049

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1090

doi:10.1107/S1600536808014049

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1,2-Bis[(2-hydroxy-3-methoxybenzylidene)hydrazono]-1,2-diphenylethane

Xiu-Ying Zhang,^a ^* Hui Ma,^a Jiu-Li Chang ^a and Xin-Cheng Wu ^a

^aHenan Normal University, College of Chemistry and Environmental Science, Xinxiang 453002, People's Republic of China
^*Correspondence e-mail: zhangxyemail@126.com

(Received 17 March 2008; accepted 10 May 2008; online 17 May 2008)

The title compound, C₃₀H₂₆N₄O₄, was synthesized by the reaction of benzyl dihydrazone and 2-hydroxy-3-methoxybenzaldehyde in ethanol. In the crystal strucutre, the molecule is centrosymmetric. The structure displays two symmetry-related intramolecular O—H⋯N hydrogen bonds.

Related literature

For related literature, see: Pankaj et al. (2000 ); Senjuti et al. (2006 ); Shubhamoy et al. (2003 ); Boudalis et al. (2004 ); Veauthier et al. (2004 ).

Experimental

Crystal data

C₃₀H₂₆N₄O₄
M_r = 506.55
Monoclinic, P 2₁ /c
a = 8.3732 (11) Å
b = 12.7267 (16) Å
c = 12.4229 (16) Å
β = 98.188 (2)°
V = 1310.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 291 (2) K
0.36 × 0.19 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.969, T_max = 0.991
9588 measured reflections
2437 independent reflections
1543 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.117
S = 1.01
2437 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	1.91	2.6350 (18)	146

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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 I, global. DOI: 10.1107/S1600536808014049/kp2163sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808014049/kp2163Isup2.hkl

checkCIF report

Comment top

The design of multidentate Schiff-base ligands and their metal complexes are of great interest in the last few years (Boudalis et al., 2004; Veauthier et al., 2224; Pal et al., 2000). The crystal structure determination of the title compound, (I), has been carried out in order to elucidate its molecular conformation. The molecule of the compound, (I), (Fig.1) is centrosymmetric with a centre of inversion in the middle of C9—C9 A bond. The two benzene rings (C10→C15 and C10 A→C15 A) are parallel. The dihedral angle between the benzene ring (C10→C15) and the least-squares best plane (C1→C6, C8, N1, O1, O2, r.m.s.= 0.0262 Å) is 74.2°. The bond lengths of C9—C9 A, N2—C9, N2—N1, N1—C8 are 1.474 (3) Å, 1.289 (2) Å, 1.4013 (19) Å, and 1.284 (2) Å, respectively. All the angles and bond lengths are within normal range (Pankaj et al., 2000). The symmetry related intramolecular hydrogen bonds O—H···N are observed (Fig. 1, Table 1).

Related literature top

For related literature, see: Pankaj et al. (2000); Senjuti et al. (2006); Shubhamoy et al. (2003); Boudalis et al. (2004); Veauthier et al. (2004).

Experimental top

All reagents were of AR grade, available commercially and used without further purification. The mixture of benzyl dihydrazone (0.595 g, 2.5 mmol), 2-hydroxy-3-methoxybenzaldehyde (0.76 g, 5 mmol) was heated and refluxed in ethanol (20 ml for 3 h, and then the resulting solution was cooled to room temperature. After filtration, the filtrate was allowed to stand at room temperature. Upon slow evaporation, yellow block crystals suitable for X-ray diffraction analysis were isolated after three days.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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. The molecular structure of (I) with atom labels and the 30% probability displacement ellipsoids for non-H atoms. The symmetry related atoms (A) are generated by symmetry operation: 1 - x, -y, 2 - z.

1,2-Bis[(2-hydroxy-3-methoxybenzylidene)hydrazono]-1,2-diphenylethane top

Crystal data top

C₃₀H₂₆N₄O₄	F(000) = 532
M_r = 506.55	D_x = 1.284 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.3732 (11) Å	Cell parameters from 1614 reflections
b = 12.7267 (16) Å	θ = 2.5–22.5°
c = 12.4229 (16) Å	µ = 0.09 mm⁻¹
β = 98.188 (2)°	T = 291 K
V = 1310.3 (3) Å³	Block, yellow
Z = 2	0.36 × 0.19 × 0.11 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2437 independent reflections
Radiation source: fine-focus sealed tube	1543 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.969, T_max = 0.991	k = −15→15
9588 measured reflections	l = −15→15

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0507P)² + 0.1624P] where P = (F_o² + 2F_c²)/3
2437 reflections	(Δ/σ)_max < 0.001
174 parameters	Δρ_max = 0.11 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₃₀H₂₆N₄O₄	V = 1310.3 (3) Å³
M_r = 506.55	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.3732 (11) Å	µ = 0.09 mm⁻¹
b = 12.7267 (16) Å	T = 291 K
c = 12.4229 (16) Å	0.36 × 0.19 × 0.11 mm
β = 98.188 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2437 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1543 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.991	R_int = 0.030
9588 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.02	Δρ_max = 0.11 e Å⁻³
2437 reflections	Δρ_min = −0.15 e Å⁻³
174 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)

are estimated using the full covariance matrix. The cell e.s.d.'s are taken

into account individually in the estimation of e.s.d.'s in distances, angles

and torsion angles; correlations between e.s.d.'s in cell parameters are only

used when they are defined by crystal symmetry. An approximate (isotropic)

treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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	0.47861 (17)	0.23761 (11)	0.56864 (11)	0.0720 (4)
O2	0.30818 (16)	0.17749 (10)	0.71864 (11)	0.0648 (4)
H2	0.2592	0.1502	0.7640	0.097*
N1	0.24208 (19)	0.03065 (11)	0.85518 (12)	0.0567 (4)
N2	0.15856 (19)	−0.02470 (11)	0.92719 (12)	0.0578 (4)
C1	0.4277 (2)	0.11223 (14)	0.69686 (15)	0.0503 (4)
C2	0.5195 (2)	0.14299 (15)	0.61656 (15)	0.0549 (5)
C3	0.6395 (2)	0.07799 (17)	0.59099 (17)	0.0661 (6)
H3	0.6997	0.0977	0.5369	0.079*
C4	0.6719 (2)	−0.01642 (16)	0.64473 (18)	0.0708 (6)
H4	0.7542	−0.0592	0.6268	0.085*
C5	0.5847 (2)	−0.04748 (15)	0.72363 (17)	0.0632 (5)
H5	0.6082	−0.1108	0.7597	0.076*
C6	0.4592 (2)	0.01623 (13)	0.75048 (14)	0.0497 (4)
C7	0.5529 (3)	0.26528 (19)	0.47601 (16)	0.0854 (7)
H7A	0.6672	0.2722	0.4972	0.128*
H7B	0.5094	0.3308	0.4468	0.128*
H7C	0.5320	0.2114	0.4217	0.128*
C8	0.3612 (2)	−0.02192 (14)	0.82838 (15)	0.0551 (5)
H8	0.3851	−0.0871	0.8605	0.066*
C9	0.0459 (2)	0.02843 (13)	0.96279 (14)	0.0499 (4)
C10	0.0056 (2)	0.14018 (13)	0.93434 (15)	0.0494 (5)
C11	−0.0776 (3)	0.16613 (16)	0.83395 (17)	0.0721 (6)
H11	−0.1114	0.1133	0.7842	0.087*
C12	−0.1110 (3)	0.26938 (19)	0.8066 (2)	0.0839 (7)
H12	−0.1656	0.2859	0.7381	0.101*
C13	−0.0644 (3)	0.34772 (17)	0.8795 (2)	0.0753 (6)
H13	−0.0891	0.4174	0.8616	0.090*
C14	0.0186 (3)	0.32303 (16)	0.97909 (19)	0.0697 (6)
H14	0.0514	0.3763	1.0286	0.084*
C15	0.0545 (2)	0.21959 (15)	1.00694 (16)	0.0600 (5)
H15	0.1117	0.2036	1.0747	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0830 (10)	0.0687 (9)	0.0680 (9)	−0.0023 (7)	0.0232 (8)	0.0159 (7)
O2	0.0686 (9)	0.0565 (8)	0.0741 (10)	0.0137 (7)	0.0271 (7)	0.0126 (7)
N1	0.0599 (10)	0.0488 (9)	0.0657 (10)	0.0003 (8)	0.0242 (8)	0.0066 (8)
N2	0.0613 (10)	0.0504 (9)	0.0656 (10)	−0.0009 (8)	0.0230 (8)	0.0070 (8)
C1	0.0488 (10)	0.0489 (10)	0.0540 (11)	−0.0016 (8)	0.0104 (8)	−0.0042 (9)
C2	0.0572 (12)	0.0540 (11)	0.0540 (11)	−0.0104 (9)	0.0100 (9)	−0.0018 (9)
C3	0.0598 (13)	0.0732 (15)	0.0701 (14)	−0.0096 (11)	0.0254 (11)	−0.0097 (11)
C4	0.0599 (13)	0.0699 (15)	0.0872 (15)	0.0049 (11)	0.0260 (12)	−0.0096 (12)
C5	0.0603 (13)	0.0521 (11)	0.0791 (14)	0.0048 (9)	0.0164 (11)	−0.0057 (10)
C6	0.0500 (11)	0.0430 (10)	0.0576 (11)	−0.0031 (8)	0.0129 (9)	−0.0038 (8)
C7	0.115 (2)	0.0852 (16)	0.0582 (13)	−0.0224 (14)	0.0215 (13)	0.0074 (11)
C8	0.0617 (12)	0.0413 (10)	0.0632 (12)	−0.0007 (9)	0.0122 (10)	0.0006 (8)
C9	0.0516 (11)	0.0463 (10)	0.0527 (11)	−0.0035 (8)	0.0108 (9)	0.0014 (8)
C10	0.0461 (10)	0.0485 (10)	0.0561 (11)	−0.0019 (8)	0.0158 (9)	0.0023 (9)
C11	0.0846 (16)	0.0638 (14)	0.0646 (14)	0.0045 (11)	−0.0004 (12)	−0.0023 (11)
C12	0.0991 (19)	0.0722 (15)	0.0766 (15)	0.0168 (13)	−0.0001 (13)	0.0155 (13)
C13	0.0737 (15)	0.0544 (13)	0.0999 (18)	0.0071 (11)	0.0203 (14)	0.0188 (13)
C14	0.0718 (14)	0.0490 (12)	0.0898 (16)	−0.0081 (10)	0.0162 (12)	−0.0057 (11)
C15	0.0643 (13)	0.0524 (12)	0.0626 (12)	−0.0043 (10)	0.0063 (10)	0.0004 (10)

Geometric parameters (Å, º) top

O1—C2	1.365 (2)	C7—H7A	0.9600
O1—C7	1.428 (2)	C7—H7B	0.9600
O2—C1	1.357 (2)	C7—H7C	0.9600
O2—H2	0.8200	C8—H8	0.9300
N1—C8	1.284 (2)	C9—C9ⁱ	1.474 (3)
N1—N2	1.4013 (19)	C9—C10	1.492 (2)
N2—C9	1.289 (2)	C10—C15	1.377 (3)
C1—C6	1.399 (2)	C10—C11	1.379 (3)
C1—C2	1.399 (2)	C11—C12	1.376 (3)
C2—C3	1.374 (3)	C11—H11	0.9300
C3—C4	1.382 (3)	C12—C13	1.366 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.362 (3)	C13—C14	1.366 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.404 (2)	C14—C15	1.383 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—C8	1.439 (2)	C15—H15	0.9300

C2—O1—C7	117.26 (16)	H7A—C7—H7C	109.5
C1—O2—H2	109.5	H7B—C7—H7C	109.5
C8—N1—N2	112.36 (15)	N1—C8—C6	122.49 (17)
C9—N2—N1	114.29 (15)	N1—C8—H8	118.8
O2—C1—C6	122.30 (16)	C6—C8—H8	118.8
O2—C1—C2	117.81 (16)	N2—C9—C9ⁱ	115.5 (2)
C6—C1—C2	119.88 (16)	N2—C9—C10	124.79 (15)
O1—C2—C3	125.21 (17)	C9ⁱ—C9—C10	119.7 (2)
O1—C2—C1	115.38 (16)	C15—C10—C11	118.76 (17)
C3—C2—C1	119.40 (18)	C15—C10—C9	120.53 (17)
C2—C3—C4	120.76 (19)	C11—C10—C9	120.69 (17)
C2—C3—H3	119.6	C12—C11—C10	120.7 (2)
C4—C3—H3	119.6	C12—C11—H11	119.6
C5—C4—C3	120.76 (19)	C10—C11—H11	119.6
C5—C4—H4	119.6	C13—C12—C11	120.3 (2)
C3—C4—H4	119.6	C13—C12—H12	119.9
C4—C5—C6	119.96 (19)	C11—C12—H12	119.9
C4—C5—H5	120.0	C14—C13—C12	119.5 (2)
C6—C5—H5	120.0	C14—C13—H13	120.2
C1—C6—C5	119.22 (16)	C12—C13—H13	120.2
C1—C6—C8	121.85 (16)	C13—C14—C15	120.6 (2)
C5—C6—C8	118.84 (17)	C13—C14—H14	119.7
O1—C7—H7A	109.5	C15—C14—H14	119.7
O1—C7—H7B	109.5	C10—C15—C14	120.05 (19)
H7A—C7—H7B	109.5	C10—C15—H15	120.0
O1—C7—H7C	109.5	C14—C15—H15	120.0

C8—N1—N2—C9	174.82 (16)	N2—N1—C8—C6	176.37 (15)
C7—O1—C2—C3	8.0 (3)	C1—C6—C8—N1	−1.7 (3)
C7—O1—C2—C1	−171.27 (17)	C5—C6—C8—N1	−178.34 (17)
O2—C1—C2—O1	0.5 (2)	N1—N2—C9—C9ⁱ	178.95 (17)
C6—C1—C2—O1	179.61 (16)	N1—N2—C9—C10	−1.4 (3)
O2—C1—C2—C3	−178.83 (16)	N2—C9—C10—C15	−102.7 (2)
C6—C1—C2—C3	0.3 (3)	C9ⁱ—C9—C10—C15	76.9 (3)
O1—C2—C3—C4	179.79 (18)	N2—C9—C10—C11	75.6 (3)
C1—C2—C3—C4	−0.9 (3)	C9ⁱ—C9—C10—C11	−104.8 (2)
C2—C3—C4—C5	0.5 (3)	C15—C10—C11—C12	0.1 (3)
C3—C4—C5—C6	0.6 (3)	C9—C10—C11—C12	−178.26 (19)
O2—C1—C6—C5	179.88 (17)	C10—C11—C12—C13	−1.1 (4)
C2—C1—C6—C5	0.8 (3)	C11—C12—C13—C14	1.4 (4)
O2—C1—C6—C8	3.3 (3)	C12—C13—C14—C15	−0.6 (3)
C2—C1—C6—C8	−175.80 (16)	C11—C10—C15—C14	0.7 (3)
C4—C5—C6—C1	−1.3 (3)	C9—C10—C15—C14	179.01 (17)
C4—C5—C6—C8	175.46 (18)	C13—C14—C15—C10	−0.4 (3)

Symmetry code: (i) −x, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.91	2.6350 (18)	146

Experimental details

Crystal data
Chemical formula	C₃₀H₂₆N₄O₄
M_r	506.55
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	8.3732 (11), 12.7267 (16), 12.4229 (16)
β (°)	98.188 (2)
V (Å³)	1310.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.36 × 0.19 × 0.11

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.969, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	9588, 2437, 1543
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.117, 1.02
No. of reflections	2437
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.15

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.91	2.6350 (18)	146.1

Acknowledgements

This work was supported by the Education Committee Department of Henan Province (grant No. 2007150027).

References

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