(E,E)-6,6'-Dimeth-oxy-2,2'-[o-phenyl-ene-bis(nitrilo-methyl-idyne)]diphenol.

In the title compound, C(22)H(20)N(2)O(4), the central benzene ring forms dihedral angles of 3.2 (2) and 61.1 (1)° with the two outer substituted benzene rings. Intra-molecular O-H⋯N hydrogen bonds are formed by both hydroxyl groups.

Related literature

For background literature concerning salen-type ligands, see: Zhang et al. (1990 ▶). For related structures, see: Lo et al. (2006 ▶).

Experimental

Crystal data

C22H20N2O4

M = 376.40

Monoclinic,

a = 6.5863 (8) Å

b = 16.726 (2) Å

c = 17.023 (3) Å

β = 97.926 (2)°

V = 1857.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.33 × 0.15 × 0.09 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.970, T max = 0.992

9269 measured reflections

3263 independent reflections

1217 reflections with I > 2σ(I)

R int = 0.098

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.128

S = 0.82

3263 reflections

257 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809008757/bi2352sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008757/bi2352Isup2.hkl

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

C22H20N2O4	F(000) = 792
Mr = 376.40	Dx = 1.346 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 802 reflections
a = 6.5863 (8) Å	θ = 2.4–25.3°
b = 16.726 (2) Å	µ = 0.09 mm−1
c = 17.023 (3) Å	T = 298 K
β = 97.926 (2)°	Block, orange
V = 1857.3 (4) Å3	0.33 × 0.15 × 0.09 mm
Z = 4

Siemens SMART CCD diffractometer	3263 independent reflections
Radiation source: fine-focus sealed tube	1217 reflections with I > 2σ(I)
graphite	Rint = 0.098
ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.970, Tmax = 0.992	k = −19→19
9269 measured reflections	l = −10→20

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 0.82	w = 1/[σ2(Fo2) + (0.0396P)2] where P = (Fo2 + 2Fc2)/3
3263 reflections	(Δ/σ)max < 0.001
257 parameters	Δρmax = 0.15 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
N1	−0.1935 (4)	0.21173 (18)	0.39296 (16)	0.0568 (8)
N2	0.0295 (4)	0.26464 (15)	0.52584 (18)	0.0579 (8)
O1	0.0593 (4)	0.15813 (15)	0.30030 (15)	0.0719 (7)
H1	0.0140	0.1899	0.3303	0.108*
O2	0.1592 (4)	0.04788 (15)	0.20699 (16)	0.0868 (9)
O3	0.2802 (3)	0.15729 (14)	0.49515 (14)	0.0676 (7)
H3	0.1719	0.1822	0.4903	0.101*
O4	0.6184 (3)	0.08108 (14)	0.53290 (13)	0.0698 (7)
C1	−0.2767 (6)	0.2731 (2)	0.4365 (2)	0.0575 (10)
C2	−0.1578 (6)	0.3022 (2)	0.5035 (2)	0.0572 (10)
C3	−0.2322 (6)	0.3642 (2)	0.5450 (2)	0.0715 (11)
H3A	−0.1540	0.3843	0.5903	0.086*
C4	−0.4199 (7)	0.3955 (2)	0.5195 (3)	0.0834 (13)
H4	−0.4689	0.4374	0.5475	0.100*
C5	−0.5373 (6)	0.3668 (3)	0.4537 (3)	0.0797 (13)
H5	−0.6659	0.3887	0.4371	0.096*
C6	−0.4654 (6)	0.3057 (2)	0.4120 (2)	0.0719 (11)
H6	−0.5451	0.2862	0.3667	0.086*
C7	−0.3021 (5)	0.1499 (2)	0.37462 (19)	0.0581 (10)
H7	−0.4285	0.1452	0.3928	0.070*
C8	−0.2348 (5)	0.0871 (2)	0.3265 (2)	0.0555 (9)
C9	−0.0623 (6)	0.0944 (2)	0.2904 (2)	0.0552 (9)
C10	−0.0088 (6)	0.0337 (2)	0.2413 (2)	0.0590 (10)
C11	−0.1242 (7)	−0.0340 (2)	0.2324 (2)	0.0754 (12)
H11	−0.0887	−0.0749	0.1998	0.090*
C12	−0.2921 (7)	−0.0425 (3)	0.2709 (3)	0.0910 (14)
H12	−0.3674	−0.0897	0.2656	0.109*
C13	−0.3491 (6)	0.0175 (3)	0.3167 (2)	0.0819 (12)
H13	−0.4654	0.0119	0.3416	0.098*
C14	0.2181 (7)	−0.0106 (2)	0.1550 (3)	0.1190 (17)
H14A	0.2234	−0.0619	0.1805	0.178*
H14B	0.3510	0.0023	0.1414	0.178*
H14C	0.1202	−0.0121	0.1077	0.178*
C15	0.1427 (6)	0.27815 (19)	0.5911 (2)	0.0595 (10)
H15	0.1003	0.3152	0.6262	0.071*
C16	0.3323 (5)	0.23818 (19)	0.6117 (2)	0.0522 (9)
C17	0.3958 (5)	0.1790 (2)	0.5627 (2)	0.0516 (9)
C18	0.5797 (5)	0.1401 (2)	0.5837 (2)	0.0543 (9)
C19	0.7041 (5)	0.1621 (2)	0.6500 (2)	0.0668 (11)
H19	0.8303	0.1371	0.6631	0.080*
C20	0.6450 (7)	0.2217 (2)	0.6987 (2)	0.0743 (12)
H20	0.7314	0.2364	0.7443	0.089*
C21	0.4615 (6)	0.2584 (2)	0.6800 (2)	0.0709 (11)
H21	0.4218	0.2977	0.7134	0.085*
C22	0.8046 (5)	0.0386 (2)	0.5504 (2)	0.0837 (13)
H22A	0.9176	0.0751	0.5522	0.125*
H22B	0.8139	−0.0008	0.5100	0.125*
H22C	0.8088	0.0126	0.6009	0.125*

	U11	U22	U33	U12	U13	U23
N1	0.064 (2)	0.059 (2)	0.0483 (18)	0.0109 (17)	0.0112 (15)	0.0045 (17)
N2	0.059 (2)	0.0576 (19)	0.057 (2)	0.0020 (16)	0.0072 (16)	−0.0030 (17)
O1	0.0748 (18)	0.0689 (18)	0.076 (2)	−0.0043 (14)	0.0235 (13)	−0.0008 (15)
O2	0.096 (2)	0.085 (2)	0.089 (2)	0.0161 (16)	0.0462 (17)	0.0009 (17)
O3	0.0697 (18)	0.0699 (17)	0.0598 (16)	0.0129 (13)	−0.0036 (13)	−0.0172 (14)
O4	0.0727 (18)	0.0755 (17)	0.0601 (16)	0.0191 (14)	0.0055 (13)	−0.0091 (15)
C1	0.067 (3)	0.054 (2)	0.054 (3)	0.009 (2)	0.020 (2)	0.016 (2)
C2	0.066 (3)	0.050 (2)	0.059 (3)	0.005 (2)	0.019 (2)	0.006 (2)
C3	0.076 (3)	0.063 (3)	0.077 (3)	0.012 (2)	0.017 (2)	−0.005 (2)
C4	0.106 (4)	0.069 (3)	0.081 (3)	0.029 (3)	0.035 (3)	0.006 (3)
C5	0.081 (3)	0.079 (3)	0.083 (3)	0.035 (3)	0.027 (3)	0.025 (3)
C6	0.077 (3)	0.080 (3)	0.059 (3)	0.024 (2)	0.013 (2)	0.015 (2)
C7	0.060 (2)	0.068 (3)	0.047 (2)	0.007 (2)	0.0104 (18)	0.010 (2)
C8	0.054 (2)	0.062 (3)	0.052 (2)	0.001 (2)	0.0114 (19)	0.008 (2)
C9	0.062 (3)	0.052 (2)	0.050 (2)	0.002 (2)	0.0035 (19)	0.007 (2)
C10	0.072 (3)	0.061 (3)	0.045 (2)	0.009 (2)	0.013 (2)	0.011 (2)
C11	0.094 (3)	0.071 (3)	0.060 (3)	0.007 (3)	0.007 (2)	−0.004 (2)
C12	0.103 (4)	0.076 (3)	0.096 (4)	−0.021 (3)	0.021 (3)	−0.015 (3)
C13	0.077 (3)	0.085 (3)	0.089 (3)	−0.018 (3)	0.027 (2)	−0.006 (3)
C14	0.157 (4)	0.110 (4)	0.106 (4)	0.039 (3)	0.073 (3)	−0.011 (3)
C15	0.076 (3)	0.048 (2)	0.058 (3)	0.002 (2)	0.020 (2)	−0.004 (2)
C16	0.061 (2)	0.044 (2)	0.053 (2)	−0.0026 (18)	0.0124 (19)	−0.0024 (19)
C17	0.058 (2)	0.053 (2)	0.043 (2)	−0.0057 (19)	0.0038 (18)	0.0003 (19)
C18	0.059 (2)	0.058 (2)	0.045 (2)	0.005 (2)	0.0057 (19)	0.001 (2)
C19	0.064 (3)	0.078 (3)	0.058 (3)	0.003 (2)	0.007 (2)	0.008 (2)
C20	0.088 (3)	0.079 (3)	0.052 (3)	−0.009 (2)	−0.002 (2)	−0.007 (2)
C21	0.088 (3)	0.068 (3)	0.055 (3)	−0.001 (2)	0.002 (2)	−0.015 (2)
C22	0.075 (3)	0.090 (3)	0.086 (3)	0.034 (2)	0.013 (2)	−0.002 (3)

N1—C7	1.272 (4)	C8—C13	1.383 (4)
N1—C1	1.419 (4)	C9—C10	1.391 (4)
N2—C15	1.270 (4)	C10—C11	1.360 (5)
N2—C2	1.389 (4)	C11—C12	1.368 (5)
O1—C9	1.330 (4)	C11—H11	0.930
O1—H1	0.820	C12—C13	1.357 (5)
O2—C10	1.342 (4)	C12—H12	0.930
O2—C14	1.409 (4)	C13—H13	0.930
O3—C17	1.339 (3)	C14—H14A	0.960
O3—H3	0.820	C14—H14B	0.960
O4—C18	1.360 (4)	C14—H14C	0.960
O4—C22	1.413 (3)	C15—C16	1.417 (4)
C1—C6	1.370 (4)	C15—H15	0.930
C1—C2	1.381 (4)	C16—C21	1.385 (4)
C2—C3	1.381 (4)	C16—C17	1.395 (4)
C3—C4	1.358 (4)	C17—C18	1.377 (4)
C3—H3A	0.930	C18—C19	1.351 (4)
C4—C5	1.358 (5)	C19—C20	1.385 (4)
C4—H4	0.930	C19—H19	0.930
C5—C6	1.365 (5)	C20—C21	1.354 (4)
C5—H5	0.930	C20—H20	0.930
C6—H6	0.930	C21—H21	0.930
C7—C8	1.439 (4)	C22—H22A	0.960
C7—H7	0.930	C22—H22B	0.960
C8—C9	1.370 (4)	C22—H22C	0.960
C7—N1—C1	118.1 (3)	C13—C12—C11	120.3 (4)
C15—N2—C2	123.4 (3)	C13—C12—H12	119.8
C9—O1—H1	109.5	C11—C12—H12	119.8
C10—O2—C14	117.7 (3)	C12—C13—C8	120.2 (4)
C17—O3—H3	109.5	C12—C13—H13	119.9
C18—O4—C22	117.7 (3)	C8—C13—H13	119.9
C6—C1—C2	119.9 (4)	O2—C14—H14A	109.5
C6—C1—N1	121.9 (4)	O2—C14—H14B	109.5
C2—C1—N1	118.1 (3)	H14A—C14—H14B	109.5
C1—C2—C3	119.1 (4)	O2—C14—H14C	109.5
C1—C2—N2	116.6 (3)	H14A—C14—H14C	109.5
C3—C2—N2	124.3 (4)	H14B—C14—H14C	109.5
C4—C3—C2	119.9 (4)	N2—C15—C16	121.6 (3)
C4—C3—H3A	120.1	N2—C15—H15	119.2
C2—C3—H3A	120.1	C16—C15—H15	119.2
C5—C4—C3	121.1 (4)	C21—C16—C17	118.3 (3)
C5—C4—H4	119.4	C21—C16—C15	120.8 (4)
C3—C4—H4	119.4	C17—C16—C15	120.9 (3)
C4—C5—C6	119.7 (4)	O3—C17—C18	118.1 (3)
C4—C5—H5	120.2	O3—C17—C16	121.6 (3)
C6—C5—H5	120.2	C18—C17—C16	120.4 (3)
C5—C6—C1	120.4 (4)	C19—C18—O4	125.7 (3)
C5—C6—H6	119.8	C19—C18—C17	119.9 (4)
C1—C6—H6	119.8	O4—C18—C17	114.4 (3)
N1—C7—C8	121.8 (4)	C18—C19—C20	120.5 (4)
N1—C7—H7	119.1	C18—C19—H19	119.8
C8—C7—H7	119.1	C20—C19—H19	119.8
C9—C8—C13	119.5 (4)	C21—C20—C19	120.1 (3)
C9—C8—C7	122.0 (4)	C21—C20—H20	120.0
C13—C8—C7	118.5 (4)	C19—C20—H20	120.0
O1—C9—C8	122.5 (4)	C20—C21—C16	120.8 (4)
O1—C9—C10	117.6 (4)	C20—C21—H21	119.6
C8—C9—C10	119.9 (4)	C16—C21—H21	119.6
O2—C10—C11	125.5 (4)	O4—C22—H22A	109.5
O2—C10—C9	115.1 (4)	O4—C22—H22B	109.5
C11—C10—C9	119.4 (4)	H22A—C22—H22B	109.5
C10—C11—C12	120.6 (4)	O4—C22—H22C	109.5
C10—C11—H11	119.7	H22A—C22—H22C	109.5
C12—C11—H11	119.7	H22B—C22—H22C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.605 (4)	146
O3—H3···N2	0.82	1.82	2.542 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.88	2.605 (4)	146
O3—H3⋯N2	0.82	1.82	2.542 (3)	146