2-Eth-oxy-6-({2-[(3-eth-oxy-2-hy-droxy-benzyl-idene)amino]-benz-yl}imino-meth-yl)phenol.

The title compound, C(25)H(26)N(2)O(4), exists in an E conformation with respect to each azomethine link. The two phenol-substituted benzene rings are twisted away from the plane of the diimine benzene ring by dihedral angles of 27.25 (5) and 56.67 (5)°. The mol-ecular structure is stabilized by intra-molecular O-H⋯N hydrogen bonds.

Related literature

For the applications of salen Schiff bases, see: Cozzi (2004 ▶); Hodnett & Dunn (1970 ▶). For the synthesis of Schiff bases, see: Tümer (2000 ▶). For a related structure, see: Aslantaş et al. (2007 ▶).

Experimental

Crystal data

C25H26N2O4

M = 418.48

Monoclinic,

a = 4.8315 (4) Å

b = 17.5414 (14) Å

c = 25.828 (2) Å

β = 94.356 (3)°

V = 2182.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.40 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.979, T max = 0.983

32150 measured reflections

3833 independent reflections

2543 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.112

S = 1.05

3833 reflections

291 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812031479/fj2580sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031479/fj2580Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031479/fj2580Isup3.cml

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

C25H26N2O4	F(000) = 888
Mr = 418.48	Dx = 1.273 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5446 reflections
a = 4.8315 (4) Å	θ = 2.3–22.4°
b = 17.5414 (14) Å	µ = 0.09 mm−1
c = 25.828 (2) Å	T = 296 K
β = 94.356 (3)°	Needle-like, orange
V = 2182.6 (3) Å3	0.40 × 0.20 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3833 independent reflections
Radiation source: fine-focus sealed tube	2543 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
ω and φ scan	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −5→5
Tmin = 0.979, Tmax = 0.983	k = −20→20
32150 measured reflections	l = −30→30

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0493P)2 + 0.3451P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3833 reflections	Δρmax = 0.13 e Å−3
291 parameters	Δρmin = −0.13 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0062 (9)

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	1.5523 (3)	1.08404 (8)	0.43051 (5)	0.0645 (4)
O2	1.1570 (3)	1.09379 (8)	0.35604 (5)	0.0598 (4)
O3	0.0532 (3)	0.93676 (8)	0.17006 (5)	0.0543 (4)
O4	−0.3152 (3)	0.82995 (8)	0.15297 (5)	0.0659 (4)
N1	0.8660 (3)	1.03221 (9)	0.27970 (5)	0.0466 (4)
N2	0.4050 (3)	1.03122 (8)	0.13518 (5)	0.0445 (4)
C1	1.8136 (6)	1.16138 (15)	0.48999 (10)	0.0968 (9)
H1A	1.8577	1.1960	0.4630	0.145*
H1B	1.9602	1.1620	0.5172	0.145*
H1C	1.6429	1.1768	0.5037	0.145*
C2	1.7824 (4)	1.08294 (13)	0.46832 (8)	0.0634 (6)
H2A	1.9497	1.0679	0.4524	0.076*
H2B	1.7496	1.0469	0.4957	0.076*
C3	1.4950 (4)	1.01888 (11)	0.40288 (7)	0.0479 (5)
C4	1.6259 (4)	0.94994 (12)	0.41106 (8)	0.0589 (5)
H4	1.7682	0.9453	0.4372	0.071*
C5	1.5485 (5)	0.88751 (12)	0.38081 (8)	0.0669 (6)
H5	1.6380	0.8411	0.3869	0.080*
C6	1.3413 (4)	0.89335 (12)	0.34193 (8)	0.0582 (5)
H6	1.2913	0.8510	0.3217	0.070*
C7	1.2044 (3)	0.96269 (10)	0.33256 (6)	0.0433 (4)
C8	1.2814 (3)	1.02555 (10)	0.36311 (7)	0.0431 (4)
C9	0.9881 (4)	0.96941 (11)	0.29046 (7)	0.0464 (5)
H9	0.9376	0.9265	0.2708	0.056*
C10	0.6616 (3)	1.03497 (11)	0.23529 (6)	0.0471 (5)
H10A	0.4828	1.0494	0.2470	0.057*
H10B	0.6430	0.9847	0.2198	0.057*
C11	0.7426 (3)	1.09114 (10)	0.19477 (7)	0.0413 (4)
C12	0.9465 (4)	1.14566 (11)	0.20497 (7)	0.0503 (5)
H12	1.0399	1.1475	0.2378	0.060*
C13	1.0149 (4)	1.19732 (11)	0.16787 (8)	0.0583 (5)
H13	1.1529	1.2334	0.1756	0.070*
C14	0.8783 (4)	1.19519 (11)	0.11950 (8)	0.0610 (6)
H14	0.9212	1.2305	0.0945	0.073*
C15	0.6775 (4)	1.14086 (11)	0.10774 (7)	0.0550 (5)
H15	0.5866	1.1394	0.0747	0.066*
C16	0.6101 (3)	1.08823 (10)	0.14499 (7)	0.0419 (4)
C17	0.3525 (4)	1.00201 (11)	0.09022 (7)	0.0468 (5)
H17	0.4510	1.0191	0.0629	0.056*
C18	0.1456 (3)	0.94344 (10)	0.08038 (7)	0.0438 (4)
C19	0.0901 (4)	0.91471 (12)	0.03008 (7)	0.0565 (5)
H19	0.1824	0.9347	0.0028	0.068*
C20	−0.0987 (4)	0.85754 (13)	0.02086 (8)	0.0636 (6)
H20	−0.1334	0.8385	−0.0126	0.076*
C21	−0.2384 (4)	0.82791 (12)	0.06090 (9)	0.0604 (6)
H21	−0.3671	0.7891	0.0541	0.072*
C22	−0.1905 (4)	0.85472 (11)	0.11067 (7)	0.0493 (5)
C23	0.0053 (3)	0.91322 (10)	0.12070 (7)	0.0430 (4)
C24	−0.4979 (4)	0.76620 (12)	0.14644 (10)	0.0709 (6)
H24A	−0.3996	0.7224	0.1341	0.085*
H24B	−0.6513	0.7780	0.1213	0.085*
C25	−0.6032 (6)	0.74931 (17)	0.19800 (12)	0.1079 (10)
H25A	−0.4492	0.7407	0.2230	0.162*
H25B	−0.7181	0.7046	0.1954	0.162*
H25C	−0.7102	0.7918	0.2088	0.162*
H2O	1.031 (4)	1.0877 (14)	0.3316 (6)	0.090 (8)*
H3O	0.172 (4)	0.9724 (10)	0.1691 (10)	0.103 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0646 (9)	0.0605 (9)	0.0640 (9)	0.0055 (7)	−0.0227 (7)	−0.0080 (7)
O2	0.0650 (9)	0.0476 (9)	0.0632 (9)	0.0063 (7)	−0.0189 (7)	−0.0030 (7)
O3	0.0597 (8)	0.0607 (9)	0.0431 (8)	−0.0100 (7)	0.0075 (6)	−0.0064 (7)
O4	0.0606 (8)	0.0640 (10)	0.0739 (10)	−0.0166 (7)	0.0109 (7)	−0.0022 (8)
N1	0.0454 (8)	0.0537 (10)	0.0400 (8)	−0.0027 (7)	−0.0006 (7)	0.0008 (7)
N2	0.0416 (8)	0.0480 (9)	0.0432 (9)	0.0004 (7)	−0.0005 (6)	0.0010 (7)
C1	0.115 (2)	0.0734 (18)	0.0933 (19)	−0.0083 (15)	−0.0501 (16)	−0.0043 (15)
C2	0.0626 (12)	0.0727 (16)	0.0519 (12)	−0.0012 (11)	−0.0152 (10)	0.0006 (11)
C3	0.0471 (10)	0.0514 (13)	0.0448 (11)	−0.0009 (9)	−0.0006 (8)	0.0009 (9)
C4	0.0594 (12)	0.0619 (14)	0.0536 (12)	0.0102 (10)	−0.0080 (10)	0.0044 (11)
C5	0.0766 (14)	0.0535 (14)	0.0691 (14)	0.0177 (11)	−0.0043 (12)	0.0057 (12)
C6	0.0705 (13)	0.0456 (12)	0.0576 (13)	0.0023 (10)	0.0004 (10)	−0.0035 (10)
C7	0.0465 (10)	0.0436 (11)	0.0400 (10)	−0.0036 (8)	0.0043 (8)	0.0056 (9)
C8	0.0451 (10)	0.0412 (11)	0.0428 (10)	0.0020 (8)	0.0031 (8)	0.0063 (9)
C9	0.0510 (10)	0.0495 (12)	0.0391 (10)	−0.0096 (9)	0.0060 (8)	−0.0006 (9)
C10	0.0421 (9)	0.0580 (12)	0.0405 (10)	−0.0053 (8)	−0.0009 (8)	0.0031 (9)
C11	0.0383 (9)	0.0430 (10)	0.0425 (10)	0.0024 (8)	0.0036 (7)	0.0001 (8)
C12	0.0482 (10)	0.0503 (12)	0.0517 (11)	−0.0047 (9)	0.0001 (9)	−0.0025 (10)
C13	0.0593 (12)	0.0485 (12)	0.0672 (14)	−0.0123 (10)	0.0059 (10)	−0.0003 (10)
C14	0.0736 (14)	0.0491 (13)	0.0609 (14)	−0.0082 (10)	0.0093 (11)	0.0105 (10)
C15	0.0641 (12)	0.0540 (13)	0.0463 (11)	−0.0020 (10)	−0.0005 (9)	0.0061 (10)
C16	0.0388 (9)	0.0429 (11)	0.0440 (10)	0.0007 (8)	0.0030 (8)	0.0002 (8)
C17	0.0482 (10)	0.0528 (12)	0.0394 (11)	0.0020 (9)	0.0032 (8)	0.0031 (9)
C18	0.0439 (9)	0.0472 (11)	0.0394 (10)	0.0044 (8)	−0.0025 (8)	−0.0033 (9)
C19	0.0628 (12)	0.0649 (14)	0.0411 (11)	0.0010 (11)	−0.0010 (9)	−0.0038 (10)
C20	0.0668 (13)	0.0709 (15)	0.0508 (13)	0.0024 (12)	−0.0115 (10)	−0.0182 (11)
C21	0.0501 (11)	0.0577 (13)	0.0712 (15)	−0.0023 (10)	−0.0094 (10)	−0.0147 (12)
C22	0.0408 (9)	0.0494 (12)	0.0573 (13)	0.0023 (9)	0.0011 (9)	−0.0023 (10)
C23	0.0402 (9)	0.0468 (11)	0.0414 (11)	0.0059 (8)	−0.0009 (8)	−0.0045 (9)
C24	0.0572 (12)	0.0480 (13)	0.1072 (19)	−0.0059 (10)	0.0038 (12)	0.0088 (12)
C25	0.099 (2)	0.093 (2)	0.134 (2)	−0.0265 (16)	0.0211 (18)	0.0369 (18)

O1—C3	1.365 (2)	C10—H10A	0.9700
O1—C2	1.423 (2)	C10—H10B	0.9700
O2—C8	1.346 (2)	C11—C12	1.384 (2)
O2—H2O	0.8502 (11)	C11—C16	1.393 (2)
O3—C23	1.343 (2)	C12—C13	1.377 (3)
O3—H3O	0.8501 (11)	C12—H12	0.9300
O4—C22	1.358 (2)	C13—C14	1.368 (3)
O4—C24	1.427 (2)	C13—H13	0.9300
N1—C9	1.270 (2)	C14—C15	1.377 (3)
N1—C10	1.456 (2)	C14—H14	0.9300
N2—C17	1.277 (2)	C15—C16	1.390 (2)
N2—C16	1.417 (2)	C15—H15	0.9300
C1—C2	1.489 (3)	C17—C18	1.443 (2)
C1—H1A	0.9600	C17—H17	0.9300
C1—H1B	0.9600	C18—C23	1.390 (2)
C1—H1C	0.9600	C18—C19	1.400 (2)
C2—H2A	0.9700	C19—C20	1.364 (3)
C2—H2B	0.9700	C19—H19	0.9300
C3—C4	1.374 (3)	C20—C21	1.379 (3)
C3—C8	1.404 (2)	C20—H20	0.9300
C4—C5	1.380 (3)	C21—C22	1.372 (3)
C4—H4	0.9300	C21—H21	0.9300
C5—C6	1.367 (3)	C22—C23	1.407 (2)
C5—H5	0.9300	C24—C25	1.491 (4)
C6—C7	1.397 (3)	C24—H24A	0.9700
C6—H6	0.9300	C24—H24B	0.9700
C7—C8	1.390 (2)	C25—H25A	0.9600
C7—C9	1.455 (2)	C25—H25B	0.9600
C9—H9	0.9300	C25—H25C	0.9600
C10—C11	1.510 (2)
C3—O1—C2	117.69 (15)	C13—C12—C11	121.82 (18)
C8—O2—H2O	106.0 (17)	C13—C12—H12	119.1
C23—O3—H3O	105.4 (18)	C11—C12—H12	119.1
C22—O4—C24	117.63 (16)	C14—C13—C12	119.52 (18)
C9—N1—C10	118.48 (16)	C14—C13—H13	120.2
C17—N2—C16	122.26 (15)	C12—C13—H13	120.2
C2—C1—H1A	109.5	C13—C14—C15	120.20 (19)
C2—C1—H1B	109.5	C13—C14—H14	119.9
H1A—C1—H1B	109.5	C15—C14—H14	119.9
C2—C1—H1C	109.5	C14—C15—C16	120.34 (18)
H1A—C1—H1C	109.5	C14—C15—H15	119.8
H1B—C1—H1C	109.5	C16—C15—H15	119.8
O1—C2—C1	107.27 (18)	C15—C16—C11	119.93 (16)
O1—C2—H2A	110.3	C15—C16—N2	122.85 (16)
C1—C2—H2A	110.3	C11—C16—N2	117.21 (15)
O1—C2—H2B	110.3	N2—C17—C18	122.22 (16)
C1—C2—H2B	110.3	N2—C17—H17	118.9
H2A—C2—H2B	108.5	C18—C17—H17	118.9
O1—C3—C4	125.73 (17)	C23—C18—C19	119.22 (17)
O1—C3—C8	114.93 (16)	C23—C18—C17	120.68 (16)
C4—C3—C8	119.35 (18)	C19—C18—C17	120.07 (17)
C3—C4—C5	120.62 (18)	C20—C19—C18	120.32 (19)
C3—C4—H4	119.7	C20—C19—H19	119.8
C5—C4—H4	119.7	C18—C19—H19	119.8
C6—C5—C4	120.56 (19)	C19—C20—C21	120.34 (19)
C6—C5—H5	119.7	C19—C20—H20	119.8
C4—C5—H5	119.7	C21—C20—H20	119.8
C5—C6—C7	120.20 (19)	C22—C21—C20	121.08 (19)
C5—C6—H6	119.9	C22—C21—H21	119.5
C7—C6—H6	119.9	C20—C21—H21	119.5
C8—C7—C6	119.32 (16)	O4—C22—C21	126.19 (18)
C8—C7—C9	120.42 (16)	O4—C22—C23	114.74 (16)
C6—C7—C9	120.25 (17)	C21—C22—C23	119.07 (18)
O2—C8—C7	122.08 (15)	O3—C23—C18	122.37 (16)
O2—C8—C3	117.98 (16)	O3—C23—C22	117.65 (16)
C7—C8—C3	119.95 (17)	C18—C23—C22	119.97 (16)
N1—C9—C7	121.94 (17)	O4—C24—C25	107.5 (2)
N1—C9—H9	119.0	O4—C24—H24A	110.2
C7—C9—H9	119.0	C25—C24—H24A	110.2
N1—C10—C11	111.81 (14)	O4—C24—H24B	110.2
N1—C10—H10A	109.3	C25—C24—H24B	110.2
C11—C10—H10A	109.3	H24A—C24—H24B	108.5
N1—C10—H10B	109.3	C24—C25—H25A	109.5
C11—C10—H10B	109.3	C24—C25—H25B	109.5
H10A—C10—H10B	107.9	H25A—C25—H25B	109.5
C12—C11—C16	118.15 (16)	C24—C25—H25C	109.5
C12—C11—C10	122.49 (16)	H25A—C25—H25C	109.5
C16—C11—C10	119.36 (15)	H25B—C25—H25C	109.5
C3—O1—C2—C1	175.91 (19)	C14—C15—C16—C11	1.1 (3)
C2—O1—C3—C4	5.6 (3)	C14—C15—C16—N2	179.84 (17)
C2—O1—C3—C8	−174.61 (16)	C12—C11—C16—C15	−2.1 (2)
O1—C3—C4—C5	179.47 (19)	C10—C11—C16—C15	178.31 (17)
C8—C3—C4—C5	−0.4 (3)	C12—C11—C16—N2	179.06 (15)
C3—C4—C5—C6	0.5 (3)	C10—C11—C16—N2	−0.5 (2)
C4—C5—C6—C7	−0.3 (3)	C17—N2—C16—C15	30.6 (3)
C5—C6—C7—C8	0.1 (3)	C17—N2—C16—C11	−150.65 (17)
C5—C6—C7—C9	178.64 (18)	C16—N2—C17—C18	179.38 (15)
C6—C7—C8—O2	−179.86 (16)	N2—C17—C18—C23	−3.8 (3)
C9—C7—C8—O2	1.6 (3)	N2—C17—C18—C19	178.20 (17)
C6—C7—C8—C3	0.0 (3)	C23—C18—C19—C20	−0.2 (3)
C9—C7—C8—C3	−178.53 (15)	C17—C18—C19—C20	177.81 (17)
O1—C3—C8—O2	0.2 (2)	C18—C19—C20—C21	0.5 (3)
C4—C3—C8—O2	179.99 (17)	C19—C20—C21—C22	−0.3 (3)
O1—C3—C8—C7	−179.72 (15)	C24—O4—C22—C21	5.1 (3)
C4—C3—C8—C7	0.1 (3)	C24—O4—C22—C23	−174.61 (16)
C10—N1—C9—C7	176.94 (14)	C20—C21—C22—O4	−179.98 (19)
C8—C7—C9—N1	1.0 (3)	C20—C21—C22—C23	−0.2 (3)
C6—C7—C9—N1	−177.52 (17)	C19—C18—C23—O3	178.33 (16)
C9—N1—C10—C11	−119.33 (18)	C17—C18—C23—O3	0.3 (3)
N1—C10—C11—C12	−14.9 (2)	C19—C18—C23—C22	−0.3 (3)
N1—C10—C11—C16	164.62 (15)	C17—C18—C23—C22	−178.31 (16)
C16—C11—C12—C13	1.6 (3)	O4—C22—C23—O3	1.6 (2)
C10—C11—C12—C13	−178.91 (17)	C21—C22—C23—O3	−178.17 (16)
C11—C12—C13—C14	0.1 (3)	O4—C22—C23—C18	−179.72 (16)
C12—C13—C14—C15	−1.2 (3)	C21—C22—C23—C18	0.5 (3)
C13—C14—C15—C16	0.6 (3)	C22—O4—C24—C25	178.99 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···N1	0.85 (1)	1.79 (1)	2.5711 (19)	151 (2)
O3—H3O···N2	0.85 (1)	1.80 (1)	2.5844 (19)	152 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯N1	0.85 (1)	1.79 (1)	2.5711 (19)	151 (2)
O3—H3O⋯N2	0.85 (1)	1.80 (1)	2.5844 (19)	152 (2)