2,2'-Diethoxy-4,4'-[(E,E)-hydrazine-diyl-idenebis(methanylylidene)]diphenol.

The complete molecule of the title compound, C(18)H(20)N(2)O(4), is generated by inversion symmetry. The conformation around the C=N bond is E. With the exception of the eth-oxy substituent, the mol-ecule is essentially planar with an r.m.s. deviation of 0.0455 Å. In the crystal, mol-ecules are linked by O-H⋯N hydrogen bonds into a two-dimensional supra-molecular network parallel to the bc plane.

Related literature

For the structure of 4,4′-(1E,1′E)-1,2-diylidenebis(methan-1-yl-1-yl­idene) bis­(2-meth­oxy­phenol), see: Qu et al. (2005 ▶). For applications of azines and their derivatives, see: Dudis et al. (1993 ▶); Facchetti et al. (2002 ▶); Kim et al. (2010 ▶); Pandeya et al. (1999 ▶); Wadher et al. (2009 ▶).

Experimental

Crystal data

C18H20N2O4

M = 328.36

Monoclinic,

a = 5.2176 (1) Å

b = 10.3422 (1) Å

c = 14.9135 (2) Å

β = 97.206 (1)°

V = 798.40 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.16 × 0.08 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996) ▶ T min = 0.650, T max = 0.746

7447 measured reflections

1831 independent reflections

1654 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.098

S = 1.05

1831 reflections

111 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812038354/zj2092sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038354/zj2092Isup2.hkl

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

C18H20N2O4	F(000) = 348
Mr = 328.36	Dx = 1.366 Mg m−3
Monoclinic, P21/n	Melting point = 471–472 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 5.2176 (1) Å	Cell parameters from 4187 reflections
b = 10.3422 (1) Å	θ = 2.4–28.4°
c = 14.9135 (2) Å	µ = 0.10 mm−1
β = 97.206 (1)°	T = 100 K
V = 798.40 (2) Å3	Block, yellow
Z = 2	0.16 × 0.08 × 0.08 mm

Bruker APEXII CCD area-detector diffractometer	1831 independent reflections
Radiation source: fine-focus sealed tube	1654 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.650, Tmax = 0.746	k = −13→13
7447 measured reflections	l = −19→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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.052P)2 + 0.3158P] where P = (Fo2 + 2Fc2)/3
1831 reflections	(Δ/σ)max < 0.001
111 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.23 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
C1	1.1226 (2)	0.61425 (10)	0.43730 (7)	0.0140 (2)
H1	1.2770	0.6254	0.4776	0.017*
C2	1.0867 (2)	0.69416 (10)	0.35602 (7)	0.0138 (2)
C3	1.2699 (2)	0.79013 (10)	0.34702 (7)	0.0150 (2)
H3	1.4163	0.7982	0.3914	0.018*
C4	1.2397 (2)	0.87397 (10)	0.27353 (7)	0.0149 (2)
H4	1.3647	0.9394	0.2683	0.018*
C5	1.0277 (2)	0.86239 (10)	0.20780 (7)	0.0137 (2)
C6	0.84916 (19)	0.76106 (10)	0.21383 (7)	0.0133 (2)
C7	0.87615 (19)	0.67949 (10)	0.28809 (7)	0.0140 (2)
H7	0.7521	0.6135	0.2931	0.017*
C8	0.4920 (2)	0.64171 (10)	0.14038 (7)	0.0163 (2)
H8B	0.3966	0.6416	0.1937	0.020*
H8A	0.5954	0.5614	0.1412	0.020*
C9	0.3053 (2)	0.64918 (12)	0.05452 (8)	0.0217 (3)
H9A	0.2111	0.7313	0.0529	0.033*
H9B	0.1825	0.5772	0.0528	0.033*
H9C	0.4011	0.6439	0.0022	0.033*
N1	0.95919 (17)	0.52993 (9)	0.45792 (6)	0.0138 (2)
O1	0.65817 (14)	0.75311 (7)	0.14250 (5)	0.0160 (2)
O2	1.00276 (14)	0.94690 (7)	0.13780 (5)	0.01629 (19)
H2	0.8462	0.9532	0.1167	0.024*

	U11	U22	U33	U12	U13	U23
C1	0.0148 (5)	0.0157 (5)	0.0109 (5)	0.0022 (4)	−0.0010 (3)	−0.0018 (4)
C2	0.0150 (5)	0.0141 (5)	0.0119 (5)	0.0026 (4)	0.0011 (4)	−0.0007 (4)
C3	0.0139 (5)	0.0169 (5)	0.0136 (5)	0.0009 (4)	−0.0013 (4)	−0.0016 (4)
C4	0.0143 (5)	0.0141 (5)	0.0162 (5)	−0.0011 (4)	0.0012 (4)	−0.0007 (4)
C5	0.0155 (5)	0.0131 (5)	0.0127 (5)	0.0020 (4)	0.0025 (4)	0.0007 (4)
C6	0.0125 (5)	0.0146 (5)	0.0123 (5)	0.0010 (4)	−0.0004 (4)	−0.0009 (4)
C7	0.0147 (5)	0.0139 (5)	0.0134 (5)	−0.0002 (4)	0.0012 (4)	0.0004 (4)
C8	0.0168 (5)	0.0154 (5)	0.0156 (5)	−0.0036 (4)	−0.0017 (4)	0.0009 (4)
C9	0.0225 (6)	0.0236 (6)	0.0172 (5)	−0.0062 (4)	−0.0043 (4)	0.0018 (4)
N1	0.0162 (4)	0.0148 (4)	0.0098 (4)	0.0031 (3)	−0.0008 (3)	0.0004 (3)
O1	0.0162 (4)	0.0167 (4)	0.0135 (4)	−0.0036 (3)	−0.0039 (3)	0.0033 (3)
O2	0.0144 (4)	0.0169 (4)	0.0167 (4)	−0.0009 (3)	−0.0014 (3)	0.0052 (3)

C1—N1	1.2835 (14)	C6—C7	1.3853 (14)
C1—C2	1.4596 (14)	C7—H7	0.9500
C1—H1	0.9500	C8—O1	1.4399 (12)
C2—C3	1.3959 (15)	C8—C9	1.5106 (14)
C2—C7	1.4062 (14)	C8—H8B	0.9900
C3—C4	1.3910 (15)	C8—H8A	0.9900
C3—H3	0.9500	C9—H9A	0.9800
C4—C5	1.3880 (14)	C9—H9B	0.9800
C4—H4	0.9500	C9—H9C	0.9800
C5—O2	1.3551 (12)	N1—N1i	1.4163 (16)
C5—C6	1.4126 (14)	O2—H2	0.8400
C6—O1	1.3658 (12)
N1—C1—C2	124.33 (9)	C6—C7—C2	120.14 (9)
N1—C1—H1	117.8	C6—C7—H7	119.9
C2—C1—H1	117.8	C2—C7—H7	119.9
C3—C2—C7	119.34 (9)	O1—C8—C9	107.47 (8)
C3—C2—C1	117.68 (9)	O1—C8—H8B	110.2
C7—C2—C1	122.98 (9)	C9—C8—H8B	110.2
C4—C3—C2	120.52 (9)	O1—C8—H8A	110.2
C4—C3—H3	119.7	C9—C8—H8A	110.2
C2—C3—H3	119.7	H8B—C8—H8A	108.5
C5—C4—C3	120.27 (10)	C8—C9—H9A	109.5
C5—C4—H4	119.9	C8—C9—H9B	109.5
C3—C4—H4	119.9	H9A—C9—H9B	109.5
O2—C5—C4	118.65 (9)	C8—C9—H9C	109.5
O2—C5—C6	121.81 (9)	H9A—C9—H9C	109.5
C4—C5—C6	119.51 (9)	H9B—C9—H9C	109.5
O1—C6—C7	125.25 (9)	C1—N1—N1i	111.99 (10)
O1—C6—C5	114.69 (9)	C6—O1—C8	116.35 (8)
C7—C6—C5	120.07 (9)	C5—O2—H2	109.5
N1—C1—C2—C3	174.08 (10)	C4—C5—C6—C7	4.43 (15)
N1—C1—C2—C7	−5.05 (16)	O1—C6—C7—C2	177.64 (9)
C7—C2—C3—C4	2.56 (15)	C5—C6—C7—C2	−2.41 (15)
C1—C2—C3—C4	−176.60 (9)	C3—C2—C7—C6	−1.07 (15)
C2—C3—C4—C5	−0.53 (16)	C1—C2—C7—C6	178.05 (9)
C3—C4—C5—O2	179.09 (9)	C2—C1—N1—N1i	−178.00 (10)
C3—C4—C5—C6	−2.96 (15)	C7—C6—O1—C8	−7.68 (15)
O2—C5—C6—O1	2.27 (14)	C5—C6—O1—C8	172.36 (9)
C4—C5—C6—O1	−175.61 (9)	C9—C8—O1—C6	−177.35 (9)
O2—C5—C6—C7	−177.68 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1ii	0.84	1.99	2.7787 (12)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1i	0.84	1.99	2.7787 (12)	156

Symmetry code: (i) .