6,6'-Dieth-oxy-2,2'-[propane-1,2-diyl-bis(nitrilo-methyl-idyne)]diphenol.

In the title mol-ecule, C(21)H(26)N(2)O(4), the dihedral angle between the two benzene rings is 88.4 (3)°. Two fairly strong intra-molecular O-H⋯N hydrogen bonds may, in part, influence the mol-ecular conformation.

Related literature

For background information on the coordination ability of tetradentate Schiff-base ligands, see: Bermejo et al. (2007 ▶); Ni et al. (2005 ▶); Nayak et al., 2006 ▶; Mohanta et al., 2002 ▶; Saha et al. (2007 ▶); Wang et al. (2008 ▶); Yu et al. (2007 ▶).

Experimental

Crystal data

C21H26N2O4

M = 370.44

Triclinic,

a = 9.140 (3) Å

b = 11.451 (4) Å

c = 13.013 (5) Å

α = 113.845 (5)°

β = 109.628 (6)°

γ = 108.812 (5)°

V = 993.5 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 273 (2) K

0.12 × 0.11 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.990, T max = 0.992

4894 measured reflections

3451 independent reflections

2325 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.193

S = 1.00

3451 reflections

249 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.26 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, 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/S1600536809003328/lh2762sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003328/lh2762Isup2.hkl

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

C21H26N2O4	Z = 2
Mr = 370.44	F(000) = 396
Triclinic, P1	Dx = 1.238 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.140 (3) Å	Cell parameters from 1361 reflections
b = 11.451 (4) Å	θ = 2.4–23.9°
c = 13.013 (5) Å	µ = 0.09 mm−1
α = 113.845 (5)°	T = 273 K
β = 109.628 (6)°	Block, yellow
γ = 108.812 (5)°	0.12 × 0.11 × 0.09 mm
V = 993.5 (6) Å3

Bruker APEXII CCD area-detector diffractometer	3451 independent reflections
Radiation source: fine-focus sealed tube	2325 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.990, Tmax = 0.992	k = −13→11
4894 measured reflections	l = −15→13

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.193	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1202P)2] where P = (Fo2 + 2Fc2)/3
3451 reflections	(Δ/σ)max < 0.001
249 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.26 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	0.2732 (2)	0.85334 (19)	0.31097 (15)	0.0615 (5)
H1	0.2881	0.8851	0.3848	0.092*
O2	0.1699 (2)	0.75251 (19)	0.06238 (15)	0.0625 (5)
O3	0.1229 (2)	0.44342 (19)	0.38472 (16)	0.0658 (5)
H3	0.1614	0.5336	0.4307	0.099*
O4	0.0549 (2)	0.16836 (19)	0.25933 (17)	0.0666 (5)
N1	0.1898 (3)	0.8527 (2)	0.4813 (2)	0.0553 (5)
N2	0.3270 (3)	0.7183 (2)	0.60118 (19)	0.0571 (5)
C1	−0.0337 (3)	0.6987 (3)	0.2479 (2)	0.0521 (6)
C2	0.0950 (3)	0.7499 (2)	0.2166 (2)	0.0477 (6)
C3	0.0365 (3)	0.6931 (3)	0.0830 (2)	0.0514 (6)
C4	−0.1454 (3)	0.5848 (3)	−0.0147 (3)	0.0621 (7)
H4	−0.1842	0.5446	−0.1036	0.075*
C5	−0.2713 (4)	0.5348 (3)	0.0171 (3)	0.0717 (8)
H5	−0.3937	0.4618	−0.0504	0.086*
C6	−0.2174 (3)	0.5916 (3)	0.1466 (3)	0.0673 (7)
H6	−0.3033	0.5588	0.1674	0.081*
C7	0.0251 (4)	0.7553 (3)	0.3859 (3)	0.0554 (6)
H7	−0.0619	0.7182	0.4045	0.067*
C8	0.1151 (4)	0.6978 (3)	−0.0732 (2)	0.0642 (7)
H8A	0.0269	0.7214	−0.1103	0.077*
H8B	0.0583	0.5892	−0.1270	0.077*
C9	0.2824 (4)	0.7724 (3)	−0.0729 (3)	0.0811 (9)
H9A	0.3376	0.8797	−0.0192	0.122*
H9B	0.2492	0.7382	−0.1626	0.122*
H9C	0.3681	0.7475	−0.0369	0.122*
C10	0.3713 (3)	0.5196 (3)	0.5889 (2)	0.0523 (6)
C11	0.2296 (3)	0.4113 (3)	0.4549 (2)	0.0509 (6)
C12	0.1958 (3)	0.2656 (3)	0.3898 (2)	0.0543 (6)
C13	0.3036 (4)	0.2294 (3)	0.4590 (3)	0.0641 (7)
H13	0.2816	0.1324	0.4161	0.077*
C14	0.4442 (4)	0.3374 (3)	0.5920 (3)	0.0722 (8)
H14	0.5158	0.3124	0.6379	0.087*
C15	0.4778 (4)	0.4803 (3)	0.6557 (3)	0.0687 (7)
H15	0.5728	0.5520	0.7446	0.082*
C16	0.4133 (3)	0.6729 (3)	0.6564 (2)	0.0563 (6)
H16	0.5092	0.7418	0.7454	0.068*
C17	0.0096 (4)	0.0166 (3)	0.1890 (3)	0.0718 (8)
H17A	−0.0139	−0.0273	0.2360	0.086*
H17B	0.1100	0.0128	0.1810	0.086*
C18	−0.1577 (5)	−0.0678 (3)	0.0545 (3)	0.0911 (10)
H18A	−0.2550	−0.0608	0.0637	0.137*
H18B	−0.1943	−0.1717	0.0050	0.137*
H18C	−0.1316	−0.0253	0.0079	0.137*
C19	0.3894 (4)	0.8780 (3)	0.6768 (2)	0.0609 (7)
H19A	0.4958	0.9345	0.6779	0.073*
H19B	0.4262	0.9145	0.7681	0.073*
C20	0.2425 (4)	0.9054 (3)	0.6181 (2)	0.0606 (7)
H20	0.1354	0.8498	0.6181	0.073*
C21	0.3133 (5)	1.0728 (3)	0.6992 (3)	0.0823 (9)
H21A	0.4190	1.1274	0.7001	0.123*
H21B	0.3464	1.1076	0.7889	0.123*
H21C	0.2192	1.0891	0.6599	0.123*

	U11	U22	U33	U12	U13	U23
O1	0.0559 (10)	0.0630 (11)	0.0471 (9)	0.0206 (9)	0.0246 (9)	0.0290 (9)
O2	0.0652 (11)	0.0655 (11)	0.0460 (9)	0.0286 (9)	0.0262 (8)	0.0316 (9)
O3	0.0776 (12)	0.0552 (11)	0.0516 (10)	0.0405 (10)	0.0184 (9)	0.0305 (9)
O4	0.0835 (12)	0.0521 (10)	0.0561 (11)	0.0391 (10)	0.0296 (10)	0.0292 (9)
N1	0.0655 (13)	0.0568 (12)	0.0575 (12)	0.0359 (11)	0.0376 (11)	0.0371 (11)
N2	0.0645 (12)	0.0497 (12)	0.0481 (12)	0.0273 (10)	0.0254 (10)	0.0279 (10)
C1	0.0525 (13)	0.0543 (14)	0.0617 (15)	0.0350 (12)	0.0305 (12)	0.0374 (13)
C2	0.0481 (13)	0.0457 (13)	0.0480 (13)	0.0267 (11)	0.0205 (11)	0.0290 (11)
C3	0.0581 (14)	0.0496 (14)	0.0507 (14)	0.0336 (12)	0.0263 (12)	0.0305 (12)
C4	0.0612 (16)	0.0656 (17)	0.0531 (15)	0.0383 (14)	0.0199 (13)	0.0346 (13)
C5	0.0499 (15)	0.0744 (19)	0.0703 (19)	0.0333 (14)	0.0175 (14)	0.0382 (16)
C6	0.0514 (15)	0.0750 (18)	0.0800 (19)	0.0363 (14)	0.0324 (15)	0.0483 (16)
C7	0.0610 (15)	0.0584 (15)	0.0669 (16)	0.0367 (13)	0.0408 (14)	0.0419 (14)
C8	0.0781 (17)	0.0652 (16)	0.0425 (13)	0.0379 (14)	0.0274 (13)	0.0302 (13)
C9	0.095 (2)	0.085 (2)	0.0584 (17)	0.0396 (18)	0.0421 (16)	0.0423 (16)
C10	0.0522 (13)	0.0598 (15)	0.0498 (13)	0.0284 (12)	0.0264 (12)	0.0370 (12)
C11	0.0558 (13)	0.0574 (15)	0.0537 (14)	0.0337 (12)	0.0300 (12)	0.0394 (12)
C12	0.0609 (15)	0.0575 (15)	0.0559 (15)	0.0335 (13)	0.0342 (13)	0.0372 (13)
C13	0.0728 (17)	0.0681 (17)	0.0798 (19)	0.0450 (15)	0.0460 (16)	0.0538 (16)
C14	0.0699 (17)	0.083 (2)	0.083 (2)	0.0471 (16)	0.0342 (16)	0.0630 (18)
C15	0.0634 (16)	0.0759 (19)	0.0646 (16)	0.0350 (15)	0.0245 (14)	0.0484 (15)
C16	0.0538 (14)	0.0562 (15)	0.0439 (13)	0.0209 (12)	0.0201 (12)	0.0291 (12)
C17	0.0860 (19)	0.0567 (17)	0.079 (2)	0.0429 (16)	0.0472 (17)	0.0374 (15)
C18	0.106 (2)	0.0601 (18)	0.080 (2)	0.0436 (18)	0.041 (2)	0.0271 (17)
C19	0.0686 (15)	0.0513 (15)	0.0475 (14)	0.0251 (13)	0.0255 (12)	0.0271 (12)
C20	0.0739 (17)	0.0623 (16)	0.0578 (15)	0.0367 (14)	0.0445 (14)	0.0359 (13)
C21	0.114 (2)	0.0701 (19)	0.081 (2)	0.0571 (19)	0.063 (2)	0.0424 (17)

O1—C2	1.341 (3)	C9—H9B	0.9600
O1—H1	0.8200	C9—H9C	0.9600
O2—C3	1.361 (3)	C10—C15	1.391 (3)
O2—C8	1.437 (3)	C10—C11	1.397 (3)
O3—C11	1.351 (3)	C10—C16	1.447 (3)
O3—H3	0.8200	C11—C12	1.394 (3)
O4—C12	1.364 (3)	C12—C13	1.387 (4)
O4—C17	1.423 (3)	C13—C14	1.388 (4)
N1—C7	1.262 (3)	C13—H13	0.9300
N1—C20	1.461 (3)	C14—C15	1.366 (4)
N2—C16	1.263 (3)	C14—H14	0.9300
N2—C19	1.461 (3)	C15—H15	0.9300
C1—C6	1.393 (3)	C16—H16	0.9300
C1—C2	1.401 (3)	C17—C18	1.489 (4)
C1—C7	1.456 (4)	C17—H17A	0.9700
C2—C3	1.404 (3)	C17—H17B	0.9700
C3—C4	1.376 (3)	C18—H18A	0.9600
C4—C5	1.382 (4)	C18—H18B	0.9600
C4—H4	0.9300	C18—H18C	0.9600
C5—C6	1.362 (4)	C19—C20	1.503 (4)
C5—H5	0.9300	C19—H19A	0.9700
C6—H6	0.9300	C19—H19B	0.9700
C7—H7	0.9300	C20—C21	1.521 (4)
C8—C9	1.490 (4)	C20—H20	0.9800
C8—H8A	0.9700	C21—H21A	0.9600
C8—H8B	0.9700	C21—H21B	0.9600
C9—H9A	0.9600	C21—H21C	0.9600
C2—O1—H1	109.5	O4—C12—C13	124.9 (2)
C3—O2—C8	116.92 (19)	O4—C12—C11	115.6 (2)
C11—O3—H3	109.5	C13—C12—C11	119.5 (2)
C12—O4—C17	118.2 (2)	C12—C13—C14	120.2 (3)
C7—N1—C20	120.5 (2)	C12—C13—H13	119.9
C16—N2—C19	118.7 (2)	C14—C13—H13	119.9
C6—C1—C2	119.9 (2)	C15—C14—C13	120.3 (2)
C6—C1—C7	120.0 (2)	C15—C14—H14	119.9
C2—C1—C7	120.1 (2)	C13—C14—H14	119.9
O1—C2—C1	122.0 (2)	C14—C15—C10	120.7 (3)
O1—C2—C3	118.7 (2)	C14—C15—H15	119.6
C1—C2—C3	119.4 (2)	C10—C15—H15	119.6
O2—C3—C4	125.7 (2)	N2—C16—C10	123.6 (2)
O2—C3—C2	115.3 (2)	N2—C16—H16	118.2
C4—C3—C2	119.1 (2)	C10—C16—H16	118.2
C3—C4—C5	121.1 (2)	O4—C17—C18	107.3 (2)
C3—C4—H4	119.4	O4—C17—H17A	110.3
C5—C4—H4	119.4	C18—C17—H17A	110.3
C6—C5—C4	120.5 (2)	O4—C17—H17B	110.3
C6—C5—H5	119.8	C18—C17—H17B	110.3
C4—C5—H5	119.8	H17A—C17—H17B	108.5
C5—C6—C1	120.0 (3)	C17—C18—H18A	109.5
C5—C6—H6	120.0	C17—C18—H18B	109.5
C1—C6—H6	120.0	H18A—C18—H18B	109.5
N1—C7—C1	122.4 (2)	C17—C18—H18C	109.5
N1—C7—H7	118.8	H18A—C18—H18C	109.5
C1—C7—H7	118.8	H18B—C18—H18C	109.5
O2—C8—C9	107.9 (2)	N2—C19—C20	112.0 (2)
O2—C8—H8A	110.1	N2—C19—H19A	109.2
C9—C8—H8A	110.1	C20—C19—H19A	109.2
O2—C8—H8B	110.1	N2—C19—H19B	109.2
C9—C8—H8B	110.1	C20—C19—H19B	109.2
H8A—C8—H8B	108.4	H19A—C19—H19B	107.9
C8—C9—H9A	109.5	N1—C20—C19	109.1 (2)
C8—C9—H9B	109.5	N1—C20—C21	109.2 (2)
H9A—C9—H9B	109.5	C19—C20—C21	110.2 (2)
C8—C9—H9C	109.5	N1—C20—H20	109.5
H9A—C9—H9C	109.5	C19—C20—H20	109.5
H9B—C9—H9C	109.5	C21—C20—H20	109.5
C15—C10—C11	119.3 (2)	C20—C21—H21A	109.5
C15—C10—C16	119.9 (2)	C20—C21—H21B	109.5
C11—C10—C16	120.8 (2)	H21A—C21—H21B	109.5
O3—C11—C12	118.1 (2)	C20—C21—H21C	109.5
O3—C11—C10	121.8 (2)	H21A—C21—H21C	109.5
C12—C11—C10	120.0 (2)	H21B—C21—H21C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.82	1.89	2.614 (3)	147
O1—H1···N1	0.82	1.85	2.576 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N2	0.82	1.89	2.614 (3)	147
O1—H1⋯N1	0.82	1.85	2.576 (2)	146