(E,E)-4,4′-Dichloro-2,2′-[azinobis(phenyl­methyl­idyne)]diphenol

Chang, J.-G.

doi:10.1107/S1600536809041427

organic compounds

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Volume 65| Part 11| November 2009| Page o2767

https://doi.org/10.1107/S1600536809041427

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(E,E)-4,4′-Dichloro-2,2′-[azinobis(phenylmethylidyne)]diphenol

Jian-Guo Chang ^a ^*

^aDepartment of Materials Science and Chemical Engineering, Taishan University, 271021 Taian,Shandong, People's Republic of China
^*Correspondence e-mail: tsucjg@163.com

(Received 25 September 2009; accepted 10 October 2009; online 17 October 2009)

The title compound, C₂₆H₁₈Cl₂N₂O₂, was synthesized by the reaction of (5-chloro-2-hydroxyphenyl)(phenyl)methanone with hydrazine hydrate. The molecule possesses a crystallographically imposed centre of symmetry at the mid-point of the N—N bond. The conformation of the molecule is stabilized by an intramolecular O—H⋯N hydrogen bond.

Related literature

For further details of the chemistry of the title compound, see: Glaser et al. (1995 ); Hunig et al. (2000 ). For similar structures, see: Kundu et al. (2005 ); Chang et al. (2007 ); Kesslen et al. (1999 ).

Experimental

Crystal data

C₂₆H₁₈Cl₂N₂O₂
M_r = 461.32
Orthorhombic, P b c n
a = 13.1622 (11) Å
b = 10.6184 (9) Å
c = 16.0671 (13) Å
V = 2245.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 295 K
0.21 × 0.19 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.925, T_max = 0.960
11062 measured reflections
1995 independent reflections
1448 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.163
S = 1.00
1995 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.85	2.572 (3)	145

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); 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 global, I. DOI: https://doi.org/10.1107/S1600536809041427/pk2195sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809041427/pk2195Isup2.hkl

checkCIF report

Comment top

Recently, a number of azine compounds containing both a diimine linkage and N—N bonding have been investigated in terms of their crystallography and coordination chemistry (Kundu et al., 2005; Kesslen et al., 1999; Chang et al., 2007;). As an extension of work on the structural characterization of azine derivatives, the title compound was synthesized and its crystal structure is reported here.

In the title compound, there is a crystallographic centre of symmetry at the midpoint of the N—N bond (Fig. 1.). The molecule displays an (E, E) conformation with respect to the C7=N1 and its symmetry related c7a=N1a double bond (Fig. 1.). This configuration agrees with those commonly found in similar compounds (Glaser et al., 1995; Hunig et al., 2000). The benzene rings, C1—C6(A), C8—C13(B) make dihedral angles of 85.26 (10)°. The conformation of the molecule is stabilized by intramolecular O—H···N hydrogen bonds. (Table 1. and Fig. 1).

Related literature top

For further details of the chemistry of the title compound, see: Glaser et al. (1995); Hunig et al. (2000). For similar structures, see: Kundu et al. (2005); Chang et al. (2007); Kesslen et al. (1999).

Experimental top

An ethanol solution (50 ml) of hydrazine (0.02 mol) and (5-chloro-2-hydroxyphenyl)(phenyl)methanone (0.04 mol) was refluxed and stirred for 6 h; the mixture was cooled and the resulting solid product, was collected by filtration. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of a solution in acetone.

Structure description top

For further details of the chemistry of the title compound, see: Glaser et al. (1995); Hunig et al. (2000). For similar structures, see: Kundu et al. (2005); Chang et al. (2007); Kesslen et al. (1999).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Dashed lines show intramolecular hydrogen bonds.

(E,E)-4,4'-Dichloro-2,2'-[azinobis(phenylmethylidyne)]diphenol top

Crystal data top

C₂₆H₁₈Cl₂N₂O₂	F(000) = 952
M_r = 461.32	D_x = 1.365 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2411 reflections
a = 13.1622 (11) Å	θ = 2.5–24.9°
b = 10.6184 (9) Å	µ = 0.32 mm⁻¹
c = 16.0671 (13) Å	T = 295 K
V = 2245.6 (3) Å³	Plate, yellow
Z = 4	0.21 × 0.19 × 0.15 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	1995 independent reflections
Radiation source: fine-focus sealed tube	1448 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
φ and ω scans	θ_max = 25.1°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −7→15
T_min = 0.925, T_max = 0.960	k = −12→12
11062 measured reflections	l = −18→19

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.113P)² + 0.120P] where P = (F_o^2^ + 2F_c^2^)/3
1995 reflections	(Δ/σ)_max < 0.001
146 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₂₆H₁₈Cl₂N₂O₂	V = 2245.6 (3) Å³
M_r = 461.32	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 13.1622 (11) Å	µ = 0.32 mm⁻¹
b = 10.6184 (9) Å	T = 295 K
c = 16.0671 (13) Å	0.21 × 0.19 × 0.15 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	1995 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1448 reflections with I > 2σ(I)
T_min = 0.925, T_max = 0.960	R_int = 0.033
11062 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.00	Δρ_max = 0.23 e Å⁻³
1995 reflections	Δρ_min = −0.41 e Å⁻³
146 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
Cl1	0.23969 (7)	0.00971 (8)	0.37894 (5)	0.0751 (4)
O1	0.0498 (2)	−0.25287 (17)	0.10094 (15)	0.0776 (7)
H1	0.0336	−0.2049	0.0632	0.116*
N1	0.01697 (18)	−0.03788 (18)	0.03234 (13)	0.0534 (6)
C1	0.0915 (2)	−0.1871 (2)	0.16297 (18)	0.0584 (8)
C2	0.09948 (19)	−0.0543 (2)	0.16200 (16)	0.0487 (7)
C3	0.1464 (2)	0.0039 (2)	0.22956 (15)	0.0502 (7)
H3	0.1534	0.0911	0.2300	0.060*
C4	0.1822 (2)	−0.0646 (2)	0.29475 (16)	0.0555 (7)
C5	0.1737 (2)	−0.1941 (3)	0.29588 (19)	0.0671 (8)
H5	0.1983	−0.2402	0.3408	0.081*
C6	0.1291 (3)	−0.2536 (3)	0.2306 (2)	0.0709 (9)
H6	0.1235	−0.3409	0.2312	0.085*
C7	0.06111 (19)	0.0215 (2)	0.09230 (15)	0.0468 (6)
C8	0.0749 (2)	0.1609 (2)	0.09250 (16)	0.0503 (7)
C9	−0.0003 (3)	0.2398 (3)	0.1189 (2)	0.0801 (10)
H9	−0.0609	0.2068	0.1391	0.096*
C10	0.0135 (3)	0.3694 (3)	0.1158 (3)	0.1007 (13)
H10	−0.0377	0.4230	0.1342	0.121*
C11	0.1022 (3)	0.4180 (3)	0.0857 (2)	0.0905 (11)
H11	0.1108	0.5048	0.0827	0.109*
C12	0.1777 (3)	0.3402 (3)	0.0602 (2)	0.0782 (10)
H12	0.2384	0.3737	0.0405	0.094*
C13	0.1644 (2)	0.2118 (3)	0.06340 (19)	0.0660 (8)
H13	0.2164	0.1587	0.0457	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0985 (7)	0.0654 (6)	0.0615 (6)	−0.0123 (4)	−0.0284 (4)	0.0114 (3)
O1	0.124 (2)	0.0360 (11)	0.0729 (14)	−0.0034 (11)	−0.0286 (14)	0.0010 (9)
N1	0.0740 (15)	0.0362 (11)	0.0500 (12)	0.0003 (10)	−0.0115 (10)	0.0046 (9)
C1	0.0757 (19)	0.0383 (14)	0.0612 (17)	0.0019 (12)	−0.0088 (14)	0.0026 (12)
C2	0.0576 (15)	0.0352 (12)	0.0533 (14)	0.0035 (11)	−0.0037 (11)	0.0052 (11)
C3	0.0596 (15)	0.0379 (12)	0.0531 (15)	−0.0002 (11)	−0.0045 (11)	0.0052 (11)
C4	0.0639 (16)	0.0462 (14)	0.0565 (15)	0.0000 (12)	−0.0074 (13)	0.0065 (12)
C5	0.084 (2)	0.0506 (16)	0.0673 (18)	0.0046 (15)	−0.0175 (15)	0.0158 (14)
C6	0.099 (2)	0.0402 (14)	0.0733 (19)	0.0036 (14)	−0.0188 (17)	0.0107 (13)
C7	0.0564 (15)	0.0362 (13)	0.0477 (13)	0.0009 (10)	−0.0035 (11)	0.0037 (10)
C8	0.0636 (16)	0.0387 (13)	0.0486 (13)	−0.0017 (12)	−0.0098 (12)	0.0031 (11)
C9	0.080 (2)	0.0472 (17)	0.113 (3)	0.0045 (15)	0.0075 (18)	−0.0080 (16)
C10	0.112 (3)	0.057 (2)	0.133 (3)	0.022 (2)	−0.006 (2)	−0.015 (2)
C11	0.128 (3)	0.0418 (18)	0.102 (3)	−0.0125 (19)	−0.032 (2)	0.0059 (17)
C12	0.104 (2)	0.0579 (19)	0.0724 (19)	−0.0258 (18)	−0.0146 (18)	0.0126 (16)
C13	0.0825 (19)	0.0504 (16)	0.0653 (17)	−0.0083 (14)	−0.0043 (15)	0.0053 (13)

Geometric parameters (Å, º) top

Cl1—C4	1.739 (3)	C6—H6	0.9300
O1—C1	1.335 (3)	C7—C8	1.491 (4)
O1—H1	0.8200	C8—C9	1.365 (4)
N1—C7	1.290 (3)	C8—C13	1.378 (4)
N1—N1ⁱ	1.388 (4)	C9—C10	1.388 (4)
C1—C6	1.387 (4)	C9—H9	0.9300
C1—C2	1.414 (4)	C10—C11	1.365 (5)
C2—C3	1.394 (4)	C10—H10	0.9300
C2—C7	1.469 (3)	C11—C12	1.355 (5)
C3—C4	1.360 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.376 (4)
C4—C5	1.381 (4)	C12—H12	0.9300
C5—C6	1.359 (4)	C13—H13	0.9300
C5—H5	0.9300

C1—O1—H1	109.5	N1—C7—C8	122.8 (2)
C7—N1—N1ⁱ	114.9 (2)	C2—C7—C8	120.0 (2)
O1—C1—C6	117.7 (2)	C9—C8—C13	119.0 (3)
O1—C1—C2	122.9 (2)	C9—C8—C7	121.5 (3)
C6—C1—C2	119.4 (3)	C13—C8—C7	119.5 (2)
C3—C2—C1	117.8 (2)	C8—C9—C10	120.2 (4)
C3—C2—C7	120.2 (2)	C8—C9—H9	119.9
C1—C2—C7	122.0 (2)	C10—C9—H9	119.9
C4—C3—C2	121.1 (2)	C11—C10—C9	120.0 (4)
C4—C3—H3	119.5	C11—C10—H10	120.0
C2—C3—H3	119.5	C9—C10—H10	120.0
C3—C4—C5	121.0 (2)	C12—C11—C10	120.2 (3)
C3—C4—Cl1	120.50 (19)	C12—C11—H11	119.9
C5—C4—Cl1	118.5 (2)	C10—C11—H11	119.9
C6—C5—C4	119.2 (2)	C11—C12—C13	120.0 (3)
C6—C5—H5	120.4	C11—C12—H12	120.0
C4—C5—H5	120.4	C13—C12—H12	120.0
C5—C6—C1	121.5 (2)	C12—C13—C8	120.6 (3)
C5—C6—H6	119.3	C12—C13—H13	119.7
C1—C6—H6	119.3	C8—C13—H13	119.7
N1—C7—C2	117.2 (2)

O1—C1—C2—C3	−178.7 (3)	C1—C2—C7—N1	1.8 (4)
C6—C1—C2—C3	0.8 (4)	C3—C2—C7—C8	1.7 (4)
O1—C1—C2—C7	0.6 (4)	C1—C2—C7—C8	−177.6 (2)
C6—C1—C2—C7	−179.9 (3)	N1—C7—C8—C9	83.9 (4)
C1—C2—C3—C4	−0.8 (4)	C2—C7—C8—C9	−96.8 (3)
C7—C2—C3—C4	179.9 (2)	N1—C7—C8—C13	−94.4 (3)
C2—C3—C4—C5	0.4 (4)	C2—C7—C8—C13	84.9 (3)
C2—C3—C4—Cl1	−179.5 (2)	C13—C8—C9—C10	0.5 (5)
C3—C4—C5—C6	0.2 (5)	C7—C8—C9—C10	−177.8 (3)
Cl1—C4—C5—C6	−180.0 (3)	C8—C9—C10—C11	0.4 (6)
C4—C5—C6—C1	−0.2 (5)	C9—C10—C11—C12	−1.2 (6)
O1—C1—C6—C5	179.2 (3)	C10—C11—C12—C13	1.0 (5)
C2—C1—C6—C5	−0.3 (5)	C11—C12—C13—C8	−0.1 (5)
N1ⁱ—N1—C7—C2	−179.4 (3)	C9—C8—C13—C12	−0.6 (4)
N1ⁱ—N1—C7—C8	0.0 (4)	C7—C8—C13—C12	177.7 (3)
C3—C2—C7—N1	−178.9 (2)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.572 (3)	145

Experimental details

Crystal data
Chemical formula	C₂₆H₁₈Cl₂N₂O₂
M_r	461.32
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	295
a, b, c (Å)	13.1622 (11), 10.6184 (9), 16.0671 (13)
V (Å³)	2245.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.21 × 0.19 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.925, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	11062, 1995, 1448
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.163, 1.00
No. of reflections	1995
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.41

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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
O1—H1···N1	0.82	1.85	2.572 (3)	145.4

Acknowledgements

This project was supported by the Postgraduate Foundation of Taishan University (No. Y05–2–09)

References

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