(E,E)-4,4'-Dichloro-2,2'-[azinobis(phenyl-methyl-idyne)]diphenol.

The title compound, C(26)H(18)Cl(2)N(2)O(2), was synthesized by the reaction of (5-chloro-2-hydroxy-phen-yl)(phen-yl)methanone with hydrazine hydrate. The mol-ecule possesses a crystallographically imposed centre of symmetry at the mid-point of the N-N bond. The conformation of the mol-ecule is stabilized by an intra-molecular 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 = 461.32

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.163

S = 1.00

1995 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.41 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809041427/pk2195sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041427/pk2195Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H18Cl2N2O2	F(000) = 952
Mr = 461.32	Dx = 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

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

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(Fo2) + (0.113P)2 + 0.120P] where P = (Fo^2^ + 2Fc^2^)/3
1995 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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