2,2'-[1,5-Bis(4-amino-phen-yl)-1,5-dihydro-benzo[1,2-d;4,5-d']diimidazole-2,6-di-yl]diphenol.

The title mol-ecule, C(32)H(24)N(6)O(2), has a crystallographic inversion centre in the middle of the benzodiimidazole core. It exists as the enol-imine tautomeric form and exhibits a strong intra-molecular O-H⋯N hydrogen bond. The dihedral angles between the planes of the 2-hy-droxy-phenyl and 4-amino-phenyl substituents and the plane of the benzodiimidazole unit [12.69 (8) and 84.71 (8)°, respectively] differ significantly due to steric reasons. In the crystal, mol-ecules are linked by C-H⋯π inter-actions, forming a two-dimensional network.

Related literature

Benzodiimidazole and its derivatives are capable of adopting various coordination modes as well as forming multiple hydrogen bonds, see: Aakeröy et al. (2001 ▶); Holman et al. (2001 ▶). For the structures of benzodiimidazole derivatives with aromatic substituents, see: Boydston et al. (2006 ▶, 2007 ▶); Lin et al. (2004 ▶). For their pharmacological applications, see: Ansari & Lal (2009 ▶); Demirayak et al. (2011 ▶); Schulz & Skibo (2000 ▶). For applications of benzodiimidazole derivatives as ligands in coordination chemistry, see: Jiang et al. (2008 ▶). Some of their metal complexes have the property of metal-to-ligand charge-transfer excited states, see: Wang et al. (2011 ▶); Ohno et al. (1992 ▶).

Experimental

Crystal data

C32H24N6O2

M = 524.57

Monoclinic,

a = 6.5181 (3) Å

b = 13.3206 (7) Å

c = 14.3081 (7) Å

β = 91.680 (4)°

V = 1241.77 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.3 × 0.1 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur CCD diffractometer

15503 measured reflections

2702 independent reflections

1605 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.123

S = 1.02

2702 reflections

190 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.16 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., 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811036737/kp2351sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036737/kp2351Isup2.hkl

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

C32H24N6O2	F(000) = 548
Mr = 524.57	Dx = 1.403 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 2702 reflections
a = 6.5181 (3) Å	θ = 4–27°
b = 13.3206 (7) Å	µ = 0.09 mm−1
c = 14.3081 (7) Å	T = 298 K
β = 91.680 (4)°	Prism, brown
V = 1241.77 (11) Å3	0.3 × 0.1 × 0.1 mm
Z = 2

Oxford Diffraction Xcalibur CCD diffractometer	1605 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.052
graphite	θmax = 27.0°, θmin = 3.7°
ω scans	h = −8→8
15503 measured reflections	k = −16→17
2702 independent reflections	l = −18→18

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0516P)2 + 0.1714P] where P = (Fo2 + 2Fc2)/3
2702 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.16 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	−0.6794 (3)	0.55326 (12)	0.29326 (12)	0.0681 (5)
H1	−0.549 (4)	0.5627 (18)	0.3187 (17)	0.082*
N1	−0.2776 (2)	0.35831 (11)	0.44335 (11)	0.0445 (4)
N2	−0.3419 (2)	0.51109 (12)	0.38381 (11)	0.0482 (4)
N3	−0.3167 (4)	−0.02530 (16)	0.60297 (17)	0.0715 (6)
H3A	−0.295 (4)	−0.077 (2)	0.5640 (19)	0.086*
H3B	−0.424 (4)	−0.0300 (19)	0.6421 (19)	0.086*
C1	−0.7197 (3)	0.45382 (16)	0.29194 (14)	0.0492 (5)
C2	−0.5877 (3)	0.38185 (15)	0.33432 (13)	0.0446 (5)
C3	−0.6341 (3)	0.28103 (16)	0.31968 (15)	0.0534 (6)
H3	−0.5461	0.2325	0.3448	0.064*
C4	−0.8066 (3)	0.25088 (17)	0.26907 (15)	0.0593 (6)
H4	−0.8327	0.1830	0.2593	0.071*
C5	−0.9399 (3)	0.32224 (19)	0.23309 (16)	0.0618 (6)
H5	−1.0591	0.3024	0.2009	0.074*
C6	−0.8976 (3)	0.42242 (18)	0.24457 (15)	0.0582 (6)
H6	−0.9891	0.4700	0.2203	0.070*
C7	−0.4052 (3)	0.41599 (15)	0.38676 (13)	0.0449 (5)
C9	−0.1660 (3)	0.51705 (14)	0.44101 (13)	0.0444 (5)
C10	−0.1229 (3)	0.42139 (14)	0.47848 (14)	0.0438 (5)
C11	0.0420 (3)	0.40088 (14)	0.53848 (14)	0.0463 (5)
H11	0.0676	0.3373	0.5630	0.056*
C12	−0.3013 (3)	0.25779 (13)	0.47880 (13)	0.0410 (5)
C13	−0.4253 (3)	0.24106 (15)	0.55365 (14)	0.0481 (5)
H13	−0.5027	0.2932	0.5777	0.058*
C14	−0.4337 (3)	0.14674 (16)	0.59246 (15)	0.0552 (6)
H14	−0.5182	0.1358	0.6427	0.066*
C15	−0.3202 (3)	0.06807 (15)	0.55872 (15)	0.0502 (5)
C16	−0.2049 (3)	0.08554 (16)	0.48043 (17)	0.0604 (6)
H16	−0.1349	0.0326	0.4535	0.072*
C17	−0.1923 (3)	0.17967 (16)	0.44203 (16)	0.0560 (6)
H17	−0.1099	0.1906	0.3910	0.067*

	U11	U22	U33	U12	U13	U23
O1	0.0738 (11)	0.0511 (10)	0.0777 (12)	0.0089 (8)	−0.0240 (9)	−0.0015 (8)
N1	0.0454 (9)	0.0404 (10)	0.0473 (10)	−0.0055 (7)	−0.0058 (8)	0.0064 (7)
N2	0.0500 (10)	0.0449 (11)	0.0492 (10)	−0.0047 (8)	−0.0061 (8)	0.0068 (8)
N3	0.0841 (15)	0.0528 (13)	0.0764 (16)	−0.0128 (11)	−0.0182 (12)	0.0168 (11)
C1	0.0499 (12)	0.0538 (14)	0.0438 (12)	0.0053 (10)	0.0007 (10)	−0.0017 (10)
C2	0.0428 (11)	0.0497 (13)	0.0414 (11)	−0.0026 (9)	0.0003 (9)	0.0031 (9)
C3	0.0566 (13)	0.0503 (13)	0.0527 (13)	−0.0070 (10)	−0.0088 (10)	0.0101 (10)
C4	0.0654 (14)	0.0585 (15)	0.0534 (14)	−0.0162 (12)	−0.0074 (11)	0.0032 (11)
C5	0.0514 (13)	0.0803 (18)	0.0532 (14)	−0.0080 (12)	−0.0085 (11)	−0.0006 (12)
C6	0.0496 (12)	0.0732 (17)	0.0513 (14)	0.0106 (11)	−0.0057 (10)	−0.0036 (11)
C7	0.0471 (11)	0.0445 (13)	0.0431 (12)	−0.0009 (9)	−0.0004 (9)	0.0047 (9)
C9	0.0456 (11)	0.0450 (12)	0.0424 (12)	−0.0014 (9)	−0.0015 (9)	0.0056 (9)
C10	0.0441 (11)	0.0420 (12)	0.0451 (12)	−0.0061 (9)	0.0002 (9)	0.0038 (9)
C11	0.0508 (11)	0.0381 (12)	0.0495 (12)	−0.0032 (9)	−0.0038 (9)	0.0102 (9)
C12	0.0434 (10)	0.0351 (11)	0.0441 (12)	−0.0027 (8)	−0.0042 (9)	0.0062 (9)
C13	0.0573 (12)	0.0428 (12)	0.0444 (12)	−0.0050 (9)	0.0048 (10)	−0.0067 (9)
C14	0.0681 (14)	0.0530 (14)	0.0447 (13)	−0.0141 (11)	0.0073 (11)	0.0008 (10)
C15	0.0524 (12)	0.0429 (13)	0.0544 (14)	−0.0091 (10)	−0.0129 (10)	0.0077 (10)
C16	0.0605 (13)	0.0451 (13)	0.0756 (17)	0.0090 (11)	0.0030 (12)	0.0007 (11)
C17	0.0539 (12)	0.0515 (14)	0.0634 (15)	0.0031 (10)	0.0168 (11)	0.0080 (11)

O1—C1	1.350 (2)	C5—C6	1.372 (3)
O1—H1	0.92 (3)	C5—H5	0.9300
N1—C7	1.378 (2)	C6—H6	0.9300
N1—C10	1.395 (2)	C9—C11i	1.386 (3)
N1—C12	1.442 (2)	C9—C10	1.407 (3)
N2—C7	1.334 (2)	C10—C11	1.383 (3)
N2—C9	1.391 (2)	C11—C9i	1.386 (3)
N3—C15	1.395 (3)	C11—H11	0.9300
N3—H3A	0.90 (3)	C12—C17	1.373 (3)
N3—H3B	0.91 (2)	C12—C13	1.379 (3)
C1—C6	1.390 (3)	C13—C14	1.375 (3)
C1—C2	1.413 (3)	C13—H13	0.9300
C2—C3	1.391 (3)	C14—C15	1.378 (3)
C2—C7	1.460 (3)	C14—H14	0.9300
C3—C4	1.379 (3)	C15—C16	1.387 (3)
C3—H3	0.9300	C16—C17	1.372 (3)
C4—C5	1.377 (3)	C16—H16	0.9300
C4—H4	0.9300	C17—H17	0.9300
C1—O1—H1	108.4 (15)	N1—C7—C2	126.65 (17)
C7—N1—C10	107.06 (15)	C11i—C9—N2	129.41 (18)
C7—N1—C12	130.96 (15)	C11i—C9—C10	121.67 (17)
C10—N1—C12	121.10 (15)	N2—C9—C10	108.92 (17)
C7—N2—C9	106.63 (16)	C11—C10—N1	130.18 (17)
C15—N3—H3A	113.7 (17)	C11—C10—C9	123.91 (17)
C15—N3—H3B	109.8 (16)	N1—C10—C9	105.91 (16)
H3A—N3—H3B	118 (2)	C10—C11—C9i	114.41 (17)
O1—C1—C6	117.47 (19)	C10—C11—H11	122.8
O1—C1—C2	122.94 (19)	C9i—C11—H11	122.8
C6—C1—C2	119.6 (2)	C17—C12—C13	119.79 (18)
C3—C2—C1	117.61 (18)	C17—C12—N1	120.46 (17)
C3—C2—C7	123.25 (18)	C13—C12—N1	119.65 (17)
C1—C2—C7	119.06 (18)	C14—C13—C12	119.50 (19)
C4—C3—C2	122.0 (2)	C14—C13—H13	120.3
C4—C3—H3	119.0	C12—C13—H13	120.3
C2—C3—H3	119.0	C13—C14—C15	121.7 (2)
C5—C4—C3	119.4 (2)	C13—C14—H14	119.2
C5—C4—H4	120.3	C15—C14—H14	119.2
C3—C4—H4	120.3	C14—C15—C16	117.68 (19)
C6—C5—C4	120.3 (2)	C14—C15—N3	121.4 (2)
C6—C5—H5	119.9	C16—C15—N3	120.9 (2)
C4—C5—H5	119.9	C17—C16—C15	121.1 (2)
C5—C6—C1	120.9 (2)	C17—C16—H16	119.4
C5—C6—H6	119.6	C15—C16—H16	119.4
C1—C6—H6	119.6	C16—C17—C12	120.1 (2)
N2—C7—N1	111.48 (16)	C16—C17—H17	120.0
N2—C7—C2	121.87 (17)	C12—C17—H17	120.0

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.92	1.76	2.582 (2)	147
C14—H14···Cgii	0.93	2.60	3.514 (2)	167

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⋯N2	0.92	1.76	2.582 (2)	147
C14—H14⋯Cgi	0.93	2.60	3.514 (2)	167

Symmetry code: (i) .