6,6'-Dieth-oxy-2,2'-[4-methyl-1,2-phenyl-enebis(nitrilo-methanylyl-idene)]diphenol aceto-nitrile monosolvate.

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

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 = 459.53

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.171

S = 0.91

4387 reflections

313 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.17 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813028845/hg5352sup1.cif

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

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

C25H26N2O4·C2H3N	F(000) = 976
Mr = 459.53	Dx = 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

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

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(Fo2) + (0.0517P)2] where P = (Fo2 + 2Fc2)/3
4387 reflections	(Δ/σ)max = 0.011
313 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.17 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	0.7285 (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)

	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)

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)

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

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