6,6′-Dieth­oxy-2,2′-[4-methyl-1,2-phenyl­enebis(nitrilo­methanylyl­idene)]diphenol aceto­nitrile monosolvate

Li, L.; Zeng, S.

doi:10.1107/S1600536813028845

organic compounds

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Volume 69| Part 11| November 2013| Page o1714

doi:10.1107/S1600536813028845

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6,6′-Diethoxy-2,2′-[4-methyl-1,2-phenylenebis(nitrilomethanylylidene)]diphenol acetonitrile monosolvate

Lei Li ^a and Suyuan Zeng ^a ^*

^aLiaocheng University, Department of Chemistry, Liaocheng, Shandong Province 252059, People's Republic of China
^*Correspondence e-mail: drzengsy@163.com

(Received 5 October 2013; accepted 21 October 2013; online 26 October 2013)

The title solvated Schiff base compound, C₂₅H₂₆N₂O₄·CH₃CN, possesses an O₂N₂ donor set affording a potentially tetradentate metal complex ligand. The central ring makes dihedral angles of 6.7 (3) and 48.4 (2)° with the pendant rings. Intramolecular N—H⋯O hydrogen-bonding interactions are observed.

CCDC reference: 967518

Related literature

For background to the properties of tetradentate Schiff-base ligands with O₂N₂ donor sets, see Zhang et al. (2009 ); Nayka et al. (2006 ). For related crystal structures, see Liu et al. (2006 ); Kargar et al. (2009 ).

Experimental

Crystal data

C₂₅H₂₆N₂O₄·C₂H₃N
M_r = 459.53
Monoclinic, P 2₁ /c
a = 11.580 (3) Å
b = 24.999 (7) Å
c = 8.995 (3) Å
β = 106.891 (6)°
V = 2491.7 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.17 × 0.11 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ) T_min = 0.986, T_max = 0.993
12206 measured reflections
4387 independent reflections
2242 reflections with I > 2σ(I)
R_int = 0.122

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.171
S = 0.91
4387 reflections
313 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.90	2.610 (5)	145
O2—H2⋯N2	0.82	1.91	2.605 (5)	142

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 967518

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813028845/hg5352sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813028845/hg5352Isup2.hkl

checkCIF report

Comment top

During the past several decades, tetradentate Schiff-base ligands with O₂N₂ donor sets have been studied intensively, partially due to the interesting magnetic properties observed for their metal complexes (Zhang et al., 2009; Nayak etal.. Herein, we present the crystal structure of a new tetradentate Schiff base ligand N,N'-Bis(2-hydroxy-3-ethoxybenzylidene)-4-methyl-1,2-phenylenediamine as its acetonitrile solvate.

As shown in Figure 1, the title compound possesses a O₂N₂ donor set affording the potentially tetradentate ligand. The imide bond lengths 1.296 (5)Å for N1—C7 and 1.269 (5)Å for N2—C16 are slightly shorter than that of related Schiff-base ligands N,N'-Bis(2-hydroxy-3-methoxybenzylidene)-1,2- phenylenediamine (Liu, et al., 2006) and 6,6'-Diethoxy-2,2'- [4,5-dimethyl-o-phenylenebis(nitrilomethylidyne)]diphenol (Kargar, et al. 2009). In this compound, two relative strong O-H···N intramolecular bonds, O1-H1···N1 and O2-H2···N2 are observed (Table 1).

Related literature top

For background to the properties of tetradentate Schiff-base ligands with O₂N₂ donor sets, see Zhang et al. (2009); Nayka et al. (2006). For related crystal structures, see Liu et al. (2006); Kargar et al. (2009).

Experimental top

The Schiff base ligand was prepared by condensation 4-methyl-1,2-phenylenediamine (10 mmol, 1.22 g) and 2-hydroxy-3-ethoxybenzaldehyde (20 mmol, 3.32 g) in a mixture of ethanol and acetonitrile(1:1). The mixture formed was allowed to partial evaporate in air for about one week to produce crystals suitable for X-ray diffraction.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

Figures top

Fig. 1. The structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. The solvent molecule has been omitted for clarity.

6,6'-Diethoxy-2,2'-[4-methyl-1,2-phenylenebis(nitrilomethanylylidene)]diphenol acetonitrile monosolvate top

Crystal data top

C₂₅H₂₆N₂O₄·C₂H₃N	F(000) = 976
M_r = 459.53	D_x = 1.225 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1236 reflections
a = 11.580 (3) Å	θ = 2.3–26.3°
b = 24.999 (7) Å	µ = 0.08 mm⁻¹
c = 8.995 (3) Å	T = 293 K
β = 106.891 (6)°	Block, orange
V = 2491.7 (12) Å³	0.17 × 0.11 × 0.09 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	4387 independent reflections
Radiation source: fine-focus sealed tube	2242 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.122
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −13→12
T_min = 0.986, T_max = 0.993	k = −29→29
12206 measured reflections	l = −4→10

Refinement top

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.171	H-atom parameters constrained
S = 0.91	w = 1/[σ²(F_o²) + (0.0517P)²] where P = (F_o² + 2F_c²)/3
4387 reflections	(Δ/σ)_max = 0.011
313 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₅H₂₆N₂O₄·C₂H₃N	V = 2491.7 (12) Å³
M_r = 459.53	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.580 (3) Å	µ = 0.08 mm⁻¹
b = 24.999 (7) Å	T = 293 K
c = 8.995 (3) Å	0.17 × 0.11 × 0.09 mm
β = 106.891 (6)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4387 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	2242 reflections with I > 2σ(I)
T_min = 0.986, T_max = 0.993	R_int = 0.122
12206 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.171	H-atom parameters constrained
S = 0.91	Δρ_max = 0.14 e Å⁻³
4387 reflections	Δρ_min = −0.17 e Å⁻³
313 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.7285 (3)	0.11495 (14)	0.4282 (4)	0.0813 (10)
H1	0.7486	0.0945	0.3688	0.122*
O2	0.5747 (3)	0.09311 (14)	0.0478 (4)	0.0904 (11)
H2	0.6313	0.0732	0.0889	0.136*
O3	0.6804 (4)	0.19431 (15)	0.5910 (4)	0.1040 (13)
O4	0.3638 (3)	0.13571 (16)	−0.0824 (4)	0.1035 (13)
N1	0.8803 (3)	0.06746 (18)	0.3066 (4)	0.0636 (11)
N2	0.7374 (3)	0.02192 (14)	0.0410 (4)	0.0625 (11)
N3	0.2332 (5)	0.1357 (3)	0.3047 (7)	0.163 (3)
C1	0.9221 (5)	0.1516 (2)	0.4400 (5)	0.0645 (13)
C2	0.8122 (5)	0.1537 (2)	0.4743 (6)	0.0672 (13)
C3	0.7888 (6)	0.1968 (2)	0.5600 (6)	0.0740 (15)
C4	0.8739 (6)	0.2366 (2)	0.6093 (6)	0.0879 (17)
H4	0.8591	0.2649	0.6682	0.105*
C5	0.9807 (6)	0.2343 (3)	0.5712 (7)	0.0958 (19)
H5	1.0361	0.2621	0.6017	0.115*
C6	1.0070 (5)	0.1926 (2)	0.4900 (6)	0.0831 (16)
H6	1.0806	0.1912	0.4679	0.100*
C7	0.9526 (4)	0.1072 (2)	0.3588 (5)	0.0668 (14)
H7	1.0283	0.1068	0.3424	0.080*
C8	0.6624 (6)	0.2277 (3)	0.7098 (7)	0.136 (2)
H8A	0.6499	0.2643	0.6729	0.163*
H8B	0.7333	0.2268	0.7995	0.163*
C9	0.5578 (7)	0.2092 (3)	0.7534 (9)	0.161 (3)
H9A	0.4886	0.2086	0.6632	0.242*
H9B	0.5428	0.2330	0.8296	0.242*
H9C	0.5727	0.1738	0.7961	0.242*
C10	0.3962 (5)	0.0948 (2)	−0.1623 (7)	0.0775 (15)
C11	0.5093 (4)	0.0717 (2)	−0.0890 (6)	0.0646 (13)
C12	0.5510 (4)	0.0303 (2)	−0.1607 (6)	0.0676 (14)
C13	0.4802 (5)	0.0110 (2)	−0.3033 (6)	0.1016 (19)
H13	0.5082	−0.0169	−0.3521	0.122*
C14	0.3700 (5)	0.0329 (3)	−0.3710 (7)	0.1034 (19)
H14	0.3226	0.0196	−0.4656	0.124*
C15	0.3277 (5)	0.0744 (2)	−0.3020 (7)	0.0897 (17)
H15	0.2520	0.0889	−0.3501	0.108*
C16	0.6679 (5)	0.00675 (19)	−0.0889 (6)	0.0761 (15)
H16	0.6935	−0.0210	−0.1406	0.091*
C17	0.2618 (5)	0.1673 (2)	−0.1656 (7)	0.119 (2)
H17A	0.1879	0.1467	−0.1840	0.142*
H17B	0.2705	0.1785	−0.2650	0.142*
C18	0.2581 (6)	0.2146 (3)	−0.0671 (8)	0.164 (3)
H18A	0.2607	0.2029	0.0355	0.246*
H18B	0.1851	0.2343	−0.1116	0.246*
H18C	0.3264	0.2371	−0.0615	0.246*
C19	0.9238 (4)	0.0225 (2)	0.2448 (6)	0.0616 (13)
C20	0.8512 (4)	−0.0026 (2)	0.1097 (6)	0.0606 (13)
C21	0.8941 (4)	−0.0476 (2)	0.0549 (5)	0.0726 (14)
H21	0.8461	−0.0644	−0.0338	0.087*
C22	1.0074 (5)	−0.0684 (2)	0.1290 (6)	0.0714 (15)
C23	1.0780 (5)	−0.0442 (2)	0.2597 (7)	0.0825 (16)
H23	1.1537	−0.0582	0.3102	0.099*
C24	1.0373 (4)	0.0007 (2)	0.3168 (5)	0.0755 (15)
H24	1.0866	0.0171	0.4056	0.091*
C25	1.0510 (4)	−0.1184 (2)	0.0656 (6)	0.1002 (18)
H25A	1.1363	−0.1158	0.0802	0.150*
H25B	1.0097	−0.1218	−0.0432	0.150*
H25C	1.0345	−0.1493	0.1197	0.150*
C26	0.4564 (5)	0.1408 (2)	0.3195 (7)	0.142 (3)
H26A	0.4775	0.1771	0.3037	0.213*
H26B	0.4710	0.1184	0.2402	0.213*
H26C	0.5046	0.1287	0.4196	0.213*
C27	0.3299 (7)	0.1382 (2)	0.3121 (7)	0.107 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.062 (2)	0.089 (3)	0.090 (3)	−0.013 (2)	0.0185 (18)	−0.025 (2)
O2	0.078 (3)	0.113 (3)	0.068 (2)	0.030 (2)	0.001 (2)	−0.010 (2)
O3	0.091 (3)	0.121 (3)	0.103 (3)	−0.009 (2)	0.032 (2)	−0.045 (2)
O4	0.088 (3)	0.118 (3)	0.095 (3)	0.047 (2)	0.013 (2)	0.004 (3)
N1	0.059 (3)	0.070 (3)	0.060 (3)	0.003 (2)	0.013 (2)	0.004 (2)
N2	0.052 (3)	0.068 (3)	0.061 (3)	0.004 (2)	0.006 (2)	0.004 (2)
N3	0.094 (4)	0.244 (7)	0.155 (5)	−0.029 (5)	0.045 (5)	0.001 (5)
C1	0.073 (4)	0.066 (4)	0.046 (3)	−0.008 (3)	0.006 (3)	−0.002 (3)
C2	0.059 (4)	0.072 (4)	0.063 (3)	0.000 (3)	0.006 (3)	0.006 (3)
C3	0.079 (4)	0.080 (4)	0.055 (4)	0.008 (4)	0.007 (3)	−0.008 (3)
C4	0.106 (5)	0.069 (4)	0.074 (4)	−0.003 (4)	0.003 (4)	−0.011 (3)
C5	0.085 (5)	0.090 (5)	0.096 (5)	−0.025 (4)	0.000 (4)	0.009 (4)
C6	0.082 (4)	0.083 (4)	0.075 (4)	−0.008 (4)	0.008 (3)	0.012 (3)
C7	0.057 (3)	0.089 (4)	0.052 (3)	−0.001 (3)	0.011 (3)	0.008 (3)
C8	0.141 (6)	0.161 (7)	0.106 (5)	0.008 (6)	0.035 (5)	−0.044 (5)
C9	0.178 (7)	0.151 (7)	0.192 (7)	−0.023 (5)	0.112 (6)	−0.049 (5)
C10	0.065 (4)	0.089 (4)	0.074 (4)	0.007 (3)	0.014 (3)	0.012 (4)
C11	0.053 (3)	0.081 (4)	0.053 (4)	−0.002 (3)	0.005 (3)	0.006 (3)
C12	0.065 (4)	0.073 (4)	0.060 (4)	0.006 (3)	0.011 (3)	−0.002 (3)
C13	0.093 (4)	0.110 (5)	0.077 (4)	0.016 (4)	−0.015 (4)	−0.018 (4)
C14	0.088 (5)	0.116 (5)	0.080 (4)	0.006 (4)	−0.016 (4)	−0.012 (4)
C15	0.069 (4)	0.110 (5)	0.075 (5)	0.002 (4)	−0.003 (4)	0.017 (4)
C16	0.070 (4)	0.085 (4)	0.070 (4)	0.015 (3)	0.015 (3)	−0.009 (3)
C17	0.099 (5)	0.125 (6)	0.121 (5)	0.047 (4)	0.014 (4)	0.035 (5)
C18	0.164 (7)	0.154 (7)	0.158 (7)	0.094 (5)	0.023 (5)	−0.004 (6)
C19	0.050 (3)	0.083 (4)	0.052 (3)	0.009 (3)	0.015 (3)	0.012 (3)
C20	0.059 (3)	0.066 (4)	0.059 (4)	0.009 (3)	0.021 (3)	0.011 (3)
C21	0.073 (4)	0.067 (4)	0.077 (4)	0.003 (3)	0.020 (3)	0.002 (3)
C22	0.082 (4)	0.067 (4)	0.078 (4)	0.027 (3)	0.043 (3)	0.021 (3)
C23	0.070 (4)	0.100 (5)	0.072 (4)	0.016 (4)	0.012 (3)	0.022 (4)
C24	0.058 (4)	0.101 (5)	0.067 (4)	0.004 (3)	0.017 (3)	0.006 (3)
C25	0.095 (4)	0.100 (4)	0.105 (4)	0.023 (4)	0.027 (4)	0.014 (4)
C26	0.061 (4)	0.164 (6)	0.192 (7)	−0.002 (4)	0.024 (4)	−0.054 (5)
C27	0.099 (5)	0.119 (5)	0.103 (5)	−0.009 (5)	0.029 (5)	−0.013 (4)

Geometric parameters (Å, º) top

O1—C2	1.347 (5)	C11—C12	1.381 (6)
O1—H1	0.8200	C12—C13	1.393 (6)
O2—C11	1.353 (5)	C12—C16	1.444 (6)
O2—H2	0.8200	C13—C14	1.361 (6)
O3—C3	1.364 (6)	C13—H13	0.9300
O3—C8	1.418 (6)	C14—C15	1.369 (6)
O4—C10	1.364 (5)	C14—H14	0.9300
O4—C17	1.437 (5)	C15—H15	0.9300
N1—C7	1.296 (5)	C16—H16	0.9300
N1—C19	1.411 (5)	C17—C18	1.486 (7)
N2—C16	1.269 (5)	C17—H17A	0.9700
N2—C20	1.421 (5)	C17—H17B	0.9700
N3—C27	1.105 (6)	C18—H18A	0.9600
C1—C2	1.394 (6)	C18—H18B	0.9600
C1—C6	1.400 (6)	C18—H18C	0.9600
C1—C7	1.428 (6)	C19—C24	1.396 (6)
C2—C3	1.397 (6)	C19—C20	1.407 (6)
C3—C4	1.379 (6)	C20—C21	1.378 (5)
C4—C5	1.377 (6)	C21—C22	1.388 (6)
C4—H4	0.9300	C21—H21	0.9300
C5—C6	1.359 (6)	C22—C23	1.362 (6)
C5—H5	0.9300	C22—C25	1.521 (6)
C6—H6	0.9300	C23—C24	1.375 (6)
C7—H7	0.9300	C23—H23	0.9300
C8—C9	1.453 (7)	C24—H24	0.9300
C8—H8A	0.9700	C25—H25A	0.9600
C8—H8B	0.9700	C25—H25B	0.9600
C9—H9A	0.9600	C25—H25C	0.9600
C9—H9B	0.9600	C26—C27	1.448 (7)
C9—H9C	0.9600	C26—H26A	0.9600
C10—C15	1.375 (6)	C26—H26B	0.9600
C10—C11	1.407 (6)	C26—H26C	0.9600

C2—O1—H1	109.5	C13—C14—H14	119.5
C11—O2—H2	109.5	C15—C14—H14	119.5
C3—O3—C8	118.2 (5)	C14—C15—C10	120.5 (5)
C10—O4—C17	116.6 (4)	C14—C15—H15	119.7
C7—N1—C19	119.2 (4)	C10—C15—H15	119.7
C16—N2—C20	122.1 (4)	N2—C16—C12	123.5 (5)
C2—C1—C6	120.2 (5)	N2—C16—H16	118.3
C2—C1—C7	121.3 (5)	C12—C16—H16	118.3
C6—C1—C7	118.5 (6)	O4—C17—C18	106.7 (5)
O1—C2—C1	121.8 (5)	O4—C17—H17A	110.4
O1—C2—C3	119.1 (5)	C18—C17—H17A	110.4
C1—C2—C3	119.1 (5)	O4—C17—H17B	110.4
O3—C3—C4	125.5 (6)	C18—C17—H17B	110.4
O3—C3—C2	114.6 (5)	H17A—C17—H17B	108.6
C4—C3—C2	119.9 (6)	C17—C18—H18A	109.5
C5—C4—C3	120.0 (6)	C17—C18—H18B	109.5
C5—C4—H4	120.0	H18A—C18—H18B	109.5
C3—C4—H4	120.0	C17—C18—H18C	109.5
C6—C5—C4	121.5 (6)	H18A—C18—H18C	109.5
C6—C5—H5	119.3	H18B—C18—H18C	109.5
C4—C5—H5	119.3	C24—C19—C20	118.3 (5)
C5—C6—C1	119.3 (6)	C24—C19—N1	121.5 (5)
C5—C6—H6	120.4	C20—C19—N1	120.2 (4)
C1—C6—H6	120.4	C21—C20—C19	119.0 (5)
N1—C7—C1	123.5 (5)	C21—C20—N2	125.5 (5)
N1—C7—H7	118.3	C19—C20—N2	115.5 (5)
C1—C7—H7	118.3	C20—C21—C22	121.5 (5)
O3—C8—C9	109.5 (6)	C20—C21—H21	119.2
O3—C8—H8A	109.8	C22—C21—H21	119.2
C9—C8—H8A	109.8	C23—C22—C21	119.6 (5)
O3—C8—H8B	109.8	C23—C22—C25	120.4 (5)
C9—C8—H8B	109.8	C21—C22—C25	119.9 (6)
H8A—C8—H8B	108.2	C22—C23—C24	120.0 (5)
C8—C9—H9A	109.5	C22—C23—H23	120.0
C8—C9—H9B	109.5	C24—C23—H23	120.0
H9A—C9—H9B	109.5	C23—C24—C19	121.5 (5)
C8—C9—H9C	109.5	C23—C24—H24	119.2
H9A—C9—H9C	109.5	C19—C24—H24	119.2
H9B—C9—H9C	109.5	C22—C25—H25A	109.5
O4—C10—C15	125.9 (5)	C22—C25—H25B	109.5
O4—C10—C11	114.9 (5)	H25A—C25—H25B	109.5
C15—C10—C11	119.2 (6)	C22—C25—H25C	109.5
O2—C11—C12	122.8 (5)	H25A—C25—H25C	109.5
O2—C11—C10	117.6 (5)	H25B—C25—H25C	109.5
C12—C11—C10	119.6 (5)	C27—C26—H26A	109.5
C11—C12—C13	119.9 (5)	C27—C26—H26B	109.5
C11—C12—C16	120.4 (5)	H26A—C26—H26B	109.5
C13—C12—C16	119.7 (5)	C27—C26—H26C	109.5
C14—C13—C12	119.8 (5)	H26A—C26—H26C	109.5
C14—C13—H13	120.1	H26B—C26—H26C	109.5
C12—C13—H13	120.1	N3—C27—C26	179.0 (8)
C13—C14—C15	121.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.90	2.610 (5)	145
O2—H2···N2	0.82	1.91	2.605 (5)	142

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.90	2.610 (5)	145
O2—H2···N2	0.82	1.91	2.605 (5)	142

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kargar, H., Kia, R., Jamshidvand, A. & Fun, H.-K. (2009). Acta Cryst. E65, o776–o777. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Liu, Y.-F., Xia, H.-T., Yang, S.-P. & Wang, D.-Q. (2006). Acta Cryst. E62, o5908–o5909. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Nayka, M., Koner, R., Lin, H. H., Florke, U., Wei, H. H. & Mohanta, S. (2006). Inorg. Chem. 45, 10764–10773. Web of Science PubMed Google Scholar
Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, D. P., Wang, H. L., Chen, Y. T., Ni, Z. H., Tian, L. J. & Jiang, J. Z. (2009). Inorg. Chem. 48, 11215–11225. Web of Science CSD CrossRef PubMed CAS Google Scholar

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Volume 69| Part 11| November 2013| Page o1714

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

6,6′-Dieth­­oxy-2,2′-[4-methyl-1,2-phenyl­enebis(nitrilo­methanylyl­­idene)]diphenol aceto­nitrile monosolvate

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Experimental

Crystal data

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Refinement

Supporting information

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organic compounds

6,6′-Diethoxy-2,2′-[4-methyl-1,2-phenylenebis(nitrilomethanylylidene)]diphenol acetonitrile monosolvate