2-{[(4-{[(2-Hy-droxy-phen-yl)(phen-yl)methyl-idene]amino}-phen-yl)imino](phen-yl)meth-yl}phenol.

The title mol-ecule, C(32)H(24)N(2)O(2), has a crystallographically imposed inversion centre and exists in the crystal as an enol-imine tautomer. The mol-ecular structure is stabilized by two strong intra-molecular O-H⋯N hydrogen bonds. The dihedral angles between the central benzene ring and the mean planes of the phenyl substituents are 59.99 (1) and 62.79 (2)°. In the crystal, the mol-ecules are arranged into (010) layers via C-H⋯π inter-actions.

Related literature

For general background to Schiff bases, see: Blagus et al. (2010 ▶). For similar structures derived from p-phenyl­enediamine, see: Al-Douh et al. (2009 ▶); Hoshino et al. (1988 ▶); Inabe et al. (1994 ▶).

Experimental

Crystal data

C32H24N2O2

M = 468.53

Orthorhombic,

a = 17.383 (4) Å

b = 14.595 (3) Å

c = 9.476 (2) Å

V = 2404.1 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.6 × 0.5 × 0.3 mm

Data collection

Oxford Diffraction Xcalibur CCD diffractometer

18421 measured reflections

2361 independent reflections

1559 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.149

S = 1.03

2361 reflections

166 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2003 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2003 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), PARST97 (Nardelli, 1995 ▶) and Mercury (Macrae et al., 2006 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811046988/gk2425sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046988/gk2425Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811046988/gk2425Isup3.cml

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

C32H24N2O2	F(000) = 984
Mr = 468.53	Dx = 1.294 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 2361 reflections
a = 17.383 (4) Å	θ = 4–26°
b = 14.595 (3) Å	µ = 0.08 mm−1
c = 9.476 (2) Å	T = 298 K
V = 2404.1 (9) Å3	Prism, red-brown
Z = 4	0.6 × 0.5 × 0.3 mm

Oxford Diffraction Xcalibur CCD diffractometer	1559 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
graphite	θmax = 26.0°, θmin = 3.8°
ω scan	h = −21→21
18421 measured reflections	k = −18→15
2361 independent reflections	l = −11→11

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0869P)2] where P = (Fo2 + 2Fc2)/3
2361 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.19 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
O1	0.10687 (9)	0.20165 (9)	0.10710 (16)	0.0382 (4)
H1	0.0915 (13)	0.1651 (16)	0.179 (3)	0.046*
N1	0.07823 (10)	0.05834 (11)	0.25539 (18)	0.0307 (4)
C1	0.13856 (11)	0.04766 (13)	0.0306 (2)	0.0291 (5)
C2	0.13707 (12)	0.14397 (13)	0.0114 (2)	0.0301 (5)
C3	0.16724 (13)	0.18187 (14)	−0.1114 (2)	0.0350 (5)
H3	0.1650	0.2449	−0.1249	0.042*
C4	0.20034 (12)	0.12759 (14)	−0.2129 (2)	0.0362 (5)
H4	0.2204	0.1542	−0.2941	0.043*
C5	0.20404 (12)	0.03367 (14)	−0.1950 (2)	0.0350 (5)
H5	0.2269	−0.0030	−0.2636	0.042*
C6	0.17364 (12)	−0.00509 (14)	−0.0750 (2)	0.0328 (5)
H6	0.1764	−0.0683	−0.0636	0.039*
C7	0.10431 (12)	0.00524 (13)	0.1571 (2)	0.0290 (5)
C8	0.10237 (12)	−0.09729 (13)	0.1671 (2)	0.0294 (5)
C9	0.05715 (13)	−0.14864 (14)	0.0762 (2)	0.0363 (6)
H9	0.0289	−0.1196	0.0059	0.044*
C10	0.05388 (14)	−0.24324 (15)	0.0898 (3)	0.0417 (6)
H10	0.0221	−0.2771	0.0306	0.050*
C11	0.09736 (14)	−0.28720 (15)	0.1902 (3)	0.0453 (6)
H11	0.0961	−0.3507	0.1973	0.054*
C12	0.14278 (13)	−0.23687 (14)	0.2802 (3)	0.0441 (6)
H12	0.1723	−0.2666	0.3481	0.053*
C13	0.14491 (12)	−0.14183 (14)	0.2704 (2)	0.0377 (6)
H13	0.1748	−0.1081	0.3330	0.045*
C14	0.03947 (12)	0.02512 (13)	0.3774 (2)	0.0289 (5)
C15	−0.02406 (13)	−0.03231 (13)	0.3698 (2)	0.0319 (5)
H15	−0.0407	−0.0539	0.2826	0.038*
C16	−0.06282 (12)	−0.05766 (14)	0.4913 (2)	0.0318 (5)
H16	−0.1049	−0.0968	0.4851	0.038*

	U11	U22	U33	U12	U13	U23
O1	0.0542 (10)	0.0276 (8)	0.0328 (9)	−0.0031 (7)	0.0041 (8)	0.0007 (7)
N1	0.0337 (10)	0.0296 (9)	0.0288 (10)	−0.0006 (8)	0.0005 (8)	0.0031 (8)
C1	0.0284 (11)	0.0310 (11)	0.0279 (12)	−0.0018 (9)	−0.0031 (9)	0.0021 (9)
C2	0.0324 (12)	0.0286 (11)	0.0293 (12)	−0.0027 (9)	−0.0026 (10)	−0.0028 (9)
C3	0.0397 (13)	0.0290 (11)	0.0364 (13)	−0.0025 (10)	−0.0036 (11)	0.0063 (10)
C4	0.0352 (12)	0.0408 (13)	0.0325 (12)	−0.0067 (10)	−0.0001 (10)	0.0037 (10)
C5	0.0341 (12)	0.0384 (13)	0.0326 (13)	0.0039 (10)	0.0028 (10)	0.0007 (10)
C6	0.0340 (12)	0.0276 (11)	0.0369 (13)	0.0001 (9)	−0.0005 (10)	0.0011 (9)
C7	0.0288 (11)	0.0291 (11)	0.0292 (12)	0.0000 (9)	−0.0036 (9)	0.0020 (9)
C8	0.0299 (11)	0.0267 (11)	0.0315 (11)	0.0008 (9)	0.0051 (10)	0.0022 (9)
C9	0.0388 (13)	0.0335 (12)	0.0367 (13)	−0.0012 (10)	−0.0004 (11)	−0.0001 (10)
C10	0.0495 (15)	0.0310 (12)	0.0444 (15)	−0.0087 (11)	0.0037 (12)	−0.0065 (11)
C11	0.0507 (15)	0.0260 (11)	0.0592 (17)	−0.0021 (11)	0.0072 (13)	0.0019 (11)
C12	0.0421 (14)	0.0341 (13)	0.0561 (16)	0.0024 (10)	−0.0005 (12)	0.0136 (11)
C13	0.0374 (13)	0.0343 (12)	0.0413 (13)	−0.0050 (10)	−0.0003 (11)	0.0060 (10)
C14	0.0346 (12)	0.0231 (10)	0.0289 (12)	0.0032 (9)	0.0024 (9)	0.0027 (9)
C15	0.0368 (13)	0.0303 (11)	0.0286 (12)	0.0017 (10)	−0.0014 (10)	−0.0020 (9)
C16	0.0317 (12)	0.0283 (11)	0.0353 (13)	−0.0026 (9)	0.0012 (10)	0.0005 (9)

O1—C2	1.344 (2)	C8—C13	1.388 (3)
O1—H1	0.91 (2)	C9—C10	1.388 (3)
N1—C7	1.294 (3)	C9—H9	0.9300
N1—C14	1.423 (3)	C10—C11	1.374 (3)
C1—C6	1.402 (3)	C10—H10	0.9300
C1—C2	1.418 (3)	C11—C12	1.375 (3)
C1—C7	1.474 (3)	C11—H11	0.9300
C2—C3	1.391 (3)	C12—C13	1.391 (3)
C3—C4	1.372 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.383 (3)	C14—C15	1.388 (3)
C4—H4	0.9300	C14—C16i	1.392 (3)
C5—C6	1.376 (3)	C15—C16	1.384 (3)
C5—H5	0.9300	C15—H15	0.9300
C6—H6	0.9300	C16—C14i	1.392 (3)
C7—C8	1.500 (3)	C16—H16	0.9300
C8—C9	1.386 (3)
C2—O1—H1	104.8 (15)	C13—C8—C7	119.99 (19)
C7—N1—C14	123.14 (17)	C8—C9—C10	120.2 (2)
C6—C1—C2	117.41 (18)	C8—C9—H9	119.9
C6—C1—C7	121.68 (18)	C10—C9—H9	119.9
C2—C1—C7	120.90 (18)	C11—C10—C9	120.4 (2)
O1—C2—C3	117.56 (18)	C11—C10—H10	119.8
O1—C2—C1	122.76 (18)	C9—C10—H10	119.8
C3—C2—C1	119.67 (19)	C10—C11—C12	119.7 (2)
C4—C3—C2	120.98 (19)	C10—C11—H11	120.1
C4—C3—H3	119.5	C12—C11—H11	120.1
C2—C3—H3	119.5	C11—C12—C13	120.4 (2)
C3—C4—C5	120.4 (2)	C11—C12—H12	119.8
C3—C4—H4	119.8	C13—C12—H12	119.8
C5—C4—H4	119.8	C8—C13—C12	120.0 (2)
C6—C5—C4	119.4 (2)	C8—C13—H13	120.0
C6—C5—H5	120.3	C12—C13—H13	120.0
C4—C5—H5	120.3	C15—C14—C16i	118.97 (18)
C5—C6—C1	122.10 (19)	C15—C14—N1	122.68 (18)
C5—C6—H6	118.9	C16i—C14—N1	118.15 (18)
C1—C6—H6	118.9	C16—C15—C14	120.35 (19)
N1—C7—C1	118.37 (18)	C16—C15—H15	119.8
N1—C7—C8	122.98 (18)	C14—C15—H15	119.8
C1—C7—C8	118.65 (17)	C15—C16—C14i	120.67 (19)
C9—C8—C13	119.14 (19)	C15—C16—H16	119.7
C9—C8—C7	120.86 (18)	C14i—C16—H16	119.7
C6—C1—C2—O1	−178.21 (19)	N1—C7—C8—C9	114.0 (2)
C7—C1—C2—O1	1.9 (3)	C1—C7—C8—C9	−67.0 (3)
C6—C1—C2—C3	2.3 (3)	N1—C7—C8—C13	−64.5 (3)
C7—C1—C2—C3	−177.61 (19)	C1—C7—C8—C13	114.5 (2)
O1—C2—C3—C4	178.80 (19)	C13—C8—C9—C10	0.8 (3)
C1—C2—C3—C4	−1.7 (3)	C7—C8—C9—C10	−177.8 (2)
C2—C3—C4—C5	0.2 (3)	C8—C9—C10—C11	−2.2 (3)
C3—C4—C5—C6	0.5 (3)	C9—C10—C11—C12	1.8 (4)
C4—C5—C6—C1	0.2 (3)	C10—C11—C12—C13	0.1 (4)
C2—C1—C6—C5	−1.6 (3)	C9—C8—C13—C12	1.0 (3)
C7—C1—C6—C5	178.34 (19)	C7—C8—C13—C12	179.6 (2)
C14—N1—C7—C1	175.68 (17)	C11—C12—C13—C8	−1.5 (3)
C14—N1—C7—C8	−5.3 (3)	C7—N1—C14—C15	−53.9 (3)
C6—C1—C7—N1	174.74 (19)	C7—N1—C14—C16i	131.3 (2)
C2—C1—C7—N1	−5.3 (3)	C16i—C14—C15—C16	−0.9 (3)
C6—C1—C7—C8	−4.3 (3)	N1—C14—C15—C16	−175.61 (18)
C2—C1—C7—C8	175.60 (19)	C14—C15—C16—C14i	0.9 (3)

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.91 (2)	1.73 (2)	2.569 (2)	152 (2)
C15—H15···Cgii	0.93	2.93	3.748 (2)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.91 (2)	1.73 (2)	2.569 (2)	152 (2)
C15—H15⋯Cgi	0.93	2.93	3.748 (2)	148

Symmetry code: (i) .