2,2'-Diazinodimethylidyne)di-o-phenyl-ene) dibenzoate.

The title compound, C(28)H(20)N(2)O(4), was synthesized by the reaction of 2-(hydrazonometh-yl)phenyl benzoate with iodine. The mol-ecule possesses a crystallographically imposed center of symmetry at the mid-point of the hydrazine N-N bond. The substituents at the ends of the C=N bonds adopt an E,E configuration. Inter-molecular C-H⋯π(arene) hydrogen bonds and aromatic π-π stacking inter-actions [centroid-centroid distance 3.900 (1) Å] link the mol-ecules into (100) sheets. In addition, there is an inter-molecular C-H⋯O hydrogen-bond inter-action.

Related literature

For related literature, see: Glaser et al. (1995 ▶); Kesslen et al. (1999 ▶); Hunig et al. (2000 ▶); Glidewell et al. (2006 ▶); Xu & Hu (2007 ▶); Zheng et al. (2006 ▶); Liu et al. (2007 ▶).

Experimental

Crystal data

C28H20N2O4

M = 448.46

Triclinic,

a = 5.5442 (9) Å

b = 7.9966 (13) Å

c = 13.455 (2) Å

α = 73.201 (2)°

β = 82.066 (3)°

γ = 74.441 (2)°

V = 548.94 (15) Å3

Z = 1

Mo Kα radiation

μ = 0.09 mm−1

T = 100 (2) K

0.35 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

2797 measured reflections

1885 independent reflections

1692 reflections with I > 2σ(I)

R int = 0.117

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.135

S = 1.03

1885 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010155/fj2111sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010155/fj2111Isup2.hkl

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

C28H20N2O4	Z = 1
Mr = 448.46	F000 = 234
Triclinic, P1	Dx = 1.357 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 5.5442 (9) Å	Cell parameters from 1976 reflections
b = 7.9966 (13) Å	θ = 2.4–27.5º
c = 13.455 (2) Å	µ = 0.09 mm−1
α = 73.201 (2)º	T = 100 (2) K
β = 82.066 (3)º	Block, pale yellow
γ = 74.441 (2)º	0.35 × 0.20 × 0.20 mm
V = 548.94 (15) Å3

Bruker SMART CCD area-detector diffractometer	1692 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.117
Monochromator: graphite	θmax = 25.0º
T = 100(2) K	θmin = 1.6º
φ and ω scans	h = −6→3
Absorption correction: none	k = −9→9
2797 measured reflections	l = −15→15
1885 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H-atom parameters constrained
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.0874P)2 + 0.0721P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
1885 reflections	Δρmax = 0.24 e Å−3
154 parameters	Δρmin = −0.28 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	−0.60203 (19)	−0.17401 (13)	0.23034 (8)	0.0250 (3)
O2	−0.3270 (2)	−0.15072 (14)	0.33163 (8)	0.0299 (3)
N1	−0.1081 (2)	0.06358 (16)	0.01102 (9)	0.0256 (3)
C1	−0.2578 (3)	−0.01150 (19)	0.07886 (11)	0.0246 (4)
H1	−0.2140	−0.1383	0.1073	0.029*
C2	−0.4964 (3)	0.09474 (19)	0.11375 (11)	0.0239 (4)
C3	−0.5716 (3)	0.2813 (2)	0.07164 (12)	0.0273 (4)
H3	−0.4643	0.3410	0.0206	0.033*
C4	−0.7999 (3)	0.3799 (2)	0.10330 (12)	0.0291 (4)
H4	−0.8471	0.5066	0.0747	0.035*
C5	−0.9593 (3)	0.2945 (2)	0.17645 (12)	0.0287 (4)
H5	−1.1170	0.3624	0.1972	0.034*
C6	−0.8898 (3)	0.1100 (2)	0.21961 (11)	0.0263 (4)
H6	−0.9986	0.0508	0.2700	0.032*
C7	−0.6600 (3)	0.01385 (19)	0.18816 (11)	0.0240 (4)
C8	−0.4341 (3)	−0.24172 (19)	0.30508 (11)	0.0228 (4)
C9	−0.3993 (3)	−0.43981 (19)	0.34806 (11)	0.0231 (4)
C10	−0.2123 (3)	−0.5285 (2)	0.41615 (12)	0.0264 (4)
H10	−0.1100	−0.4633	0.4326	0.032*
C11	−0.1736 (3)	−0.7120 (2)	0.46053 (12)	0.0283 (4)
H11	−0.0454	−0.7729	0.5076	0.034*
C12	−0.3236 (3)	−0.8067 (2)	0.43577 (12)	0.0293 (4)
H12	−0.2985	−0.9326	0.4664	0.035*
C13	−0.5087 (3)	−0.7186 (2)	0.36691 (12)	0.0287 (4)
H13	−0.6087	−0.7845	0.3496	0.034*
C14	−0.5495 (3)	−0.5342 (2)	0.32285 (12)	0.0264 (4)
H14	−0.6781	−0.4733	0.2761	0.032*

	U11	U22	U33	U12	U13	U23
O1	0.0317 (6)	0.0174 (6)	0.0274 (6)	−0.0070 (4)	−0.0069 (4)	−0.0048 (4)
O2	0.0394 (6)	0.0212 (6)	0.0337 (6)	−0.0127 (5)	−0.0095 (5)	−0.0061 (4)
N1	0.0305 (7)	0.0198 (6)	0.0267 (7)	−0.0039 (5)	−0.0036 (5)	−0.0077 (5)
C1	0.0334 (8)	0.0167 (7)	0.0249 (7)	−0.0057 (6)	−0.0065 (6)	−0.0058 (6)
C2	0.0307 (8)	0.0199 (8)	0.0233 (7)	−0.0067 (6)	−0.0049 (6)	−0.0073 (6)
C3	0.0328 (8)	0.0211 (8)	0.0280 (8)	−0.0075 (6)	−0.0037 (6)	−0.0049 (6)
C4	0.0362 (9)	0.0177 (7)	0.0329 (8)	−0.0037 (6)	−0.0076 (6)	−0.0061 (6)
C5	0.0290 (8)	0.0261 (8)	0.0326 (8)	−0.0023 (6)	−0.0052 (6)	−0.0129 (6)
C6	0.0294 (8)	0.0265 (8)	0.0264 (8)	−0.0095 (6)	−0.0026 (6)	−0.0093 (6)
C7	0.0317 (8)	0.0176 (7)	0.0257 (8)	−0.0062 (6)	−0.0089 (6)	−0.0068 (6)
C8	0.0270 (7)	0.0201 (8)	0.0224 (7)	−0.0067 (6)	−0.0005 (6)	−0.0070 (6)
C9	0.0274 (8)	0.0201 (8)	0.0240 (7)	−0.0077 (6)	0.0005 (6)	−0.0083 (6)
C10	0.0311 (8)	0.0226 (8)	0.0285 (8)	−0.0090 (6)	−0.0039 (6)	−0.0083 (6)
C11	0.0316 (8)	0.0223 (8)	0.0293 (8)	−0.0043 (6)	−0.0047 (6)	−0.0050 (6)
C12	0.0360 (9)	0.0169 (7)	0.0337 (8)	−0.0064 (6)	0.0019 (6)	−0.0065 (6)
C13	0.0318 (8)	0.0222 (8)	0.0366 (9)	−0.0108 (6)	−0.0003 (6)	−0.0114 (6)
C14	0.0283 (8)	0.0214 (8)	0.0310 (8)	−0.0069 (6)	−0.0028 (6)	−0.0081 (6)

O1—C8	1.3580 (18)	C6—C7	1.381 (2)
O1—C7	1.4073 (17)	C6—H6	0.9500
O2—C8	1.2045 (17)	C8—C9	1.489 (2)
N1—C1	1.274 (2)	C9—C10	1.382 (2)
N1—N1i	1.408 (2)	C9—C14	1.393 (2)
C1—C2	1.466 (2)	C10—C11	1.384 (2)
C1—H1	0.9500	C10—H10	0.9500
C2—C7	1.390 (2)	C11—C12	1.392 (2)
C2—C3	1.401 (2)	C11—H11	0.9500
C3—C4	1.384 (2)	C12—C13	1.380 (2)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.383 (2)	C13—C14	1.389 (2)
C4—H4	0.9500	C13—H13	0.9500
C5—C6	1.387 (2)	C14—H14	0.9500
C5—H5	0.9500
C8—O1—C7	116.52 (10)	C2—C7—O1	120.43 (13)
C1—N1—N1i	111.37 (15)	O2—C8—O1	123.28 (13)
N1—C1—C2	121.02 (13)	O2—C8—C9	125.08 (13)
N1—C1—H1	119.5	O1—C8—C9	111.63 (12)
C2—C1—H1	119.5	C10—C9—C14	120.38 (14)
C7—C2—C3	117.32 (14)	C10—C9—C8	117.36 (13)
C7—C2—C1	121.33 (13)	C14—C9—C8	122.25 (13)
C3—C2—C1	121.33 (13)	C9—C10—C11	120.26 (13)
C4—C3—C2	120.94 (14)	C9—C10—H10	119.9
C4—C3—H3	119.5	C11—C10—H10	119.9
C2—C3—H3	119.5	C10—C11—C12	119.53 (14)
C5—C4—C3	120.14 (14)	C10—C11—H11	120.2
C5—C4—H4	119.9	C12—C11—H11	120.2
C3—C4—H4	119.9	C13—C12—C11	120.28 (14)
C4—C5—C6	120.20 (14)	C13—C12—H12	119.9
C4—C5—H5	119.9	C11—C12—H12	119.9
C6—C5—H5	119.9	C12—C13—C14	120.35 (13)
C7—C6—C5	118.95 (14)	C12—C13—H13	119.8
C7—C6—H6	120.5	C14—C13—H13	119.8
C5—C6—H6	120.5	C13—C14—C9	119.19 (14)
C6—C7—C2	122.43 (14)	C13—C14—H14	120.4
C6—C7—O1	117.04 (13)	C9—C14—H14	120.4
N1i—N1—C1—C2	−179.77 (13)	C8—O1—C7—C2	78.69 (16)
N1—C1—C2—C7	−179.63 (13)	C7—O1—C8—O2	−3.9 (2)
N1—C1—C2—C3	1.9 (2)	C7—O1—C8—C9	176.64 (11)
C7—C2—C3—C4	0.0 (2)	O2—C8—C9—C10	−6.7 (2)
C1—C2—C3—C4	178.48 (13)	O1—C8—C9—C10	172.76 (12)
C2—C3—C4—C5	−0.9 (2)	O2—C8—C9—C14	172.44 (14)
C3—C4—C5—C6	1.0 (2)	O1—C8—C9—C14	−8.13 (19)
C4—C5—C6—C7	−0.1 (2)	C14—C9—C10—C11	−0.4 (2)
C5—C6—C7—C2	−0.8 (2)	C8—C9—C10—C11	178.68 (12)
C5—C6—C7—O1	−177.14 (12)	C9—C10—C11—C12	0.3 (2)
C3—C2—C7—C6	0.9 (2)	C10—C11—C12—C13	0.4 (2)
C1—C2—C7—C6	−177.63 (13)	C11—C12—C13—C14	−1.0 (2)
C3—C2—C7—O1	177.10 (12)	C12—C13—C14—C9	0.8 (2)
C1—C2—C7—O1	−1.4 (2)	C10—C9—C14—C13	−0.1 (2)
C8—O1—C7—C6	−104.90 (14)	C8—C9—C14—C13	−179.14 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ii	0.95	2.64	3.519 (2)	154
C5—H5···Cg1iii	0.95	2.79	3.510 (2)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.95	2.64	3.519 (2)	154
C5—H5⋯Cg1ii	0.95	2.79	3.510 (2)	133

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C9–C14 ring.