2-Eth­oxy-6-({2-[(3-eth­oxy-2-hy­droxy­benzyl­idene)amino]­benz­yl}imino­meth­yl)phenol

Ambili, K.U.; Sreejith, S.S.; Jacob, J.M.; Sithambaresan, M.; Kurup, M.R.P.

doi:10.1107/S1600536812031479

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2482

https://doi.org/10.1107/S1600536812031479

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2-Ethoxy-6-({2-[(3-ethoxy-2-hydroxybenzylidene)amino]benzyl}iminomethyl)phenol

K. U. Ambili,^a S. S. Sreejith,^a Jinsa Mary Jacob,^a M. Sithambaresan ^b ^* and M. R. Prathapachandra Kurup ^a

^aDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India, and ^bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka
^*Correspondence e-mail: eesans@yahoo.com

(Received 27 June 2012; accepted 10 July 2012; online 18 July 2012)

The title compound, C₂₅H₂₆N₂O₄, 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 molecular structure is stabilized by intramolecular 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_r = 418.48
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.038
wR(F²) = 0.112
S = 1.05
3833 reflections
291 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.13 e Å⁻³

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)

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812031479/fj2580sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812031479/fj2580Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812031479/fj2580Isup3.cml

checkCIF report

Comment top

The chelating structure, moderate electron donation and easy tunable electronic and steric effects make dicompartmental salen type Schiff bases to act as versatile ligands. They are able to stabilize different metals in various oxidation states and control the performance of the metals in various catalytic transformations (Cozzi, 2004). Schiff bases are very selective in the sense that they provide geometrical cavity control for host guest interaction and modulate its lipophilicity to stabilize a specific metal ion. Moreover, it has been suggested that the azomethine linkage in Schiff bases is responsible for their biological activities such as antimicrobial, antifungal and antitumor and also to be used as herbicides (Hodnett & Dunn, 1970).

The E conformation of the compound is evidenced from the torsion angles, 176.94 (14)° and 179.38 (15)° made by the C10—N1—C9—C7 and C16—N2—C17—C18 linkages respectively. The bond lengths and bond angles are in normal ranges and agree with the related structure (Aslantaş, et al., 2007). The crystal involves two intramolecular O—H···N hydrogen bonds and C—H···π interactions which make the molecule stable.

Related literature top

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 top

The title compound was prepared according to the reported procedure (Tümer, 2000) by the condensation of the ethanolic solution of 3-ethoxy-2-hydroxybenzaldehyde (1 mmol, 0.166 g) with an ethanolic solution of 2-aminobenzylamine (0.5 mmol, 0.061 g). The reaction mixture was heated to reflux for 6 h and kept for cooling at room temperature. The slow evaporation yielded orange-yellow crystals of N,N'-bis(3-ethoxy-2-hydroxybenzylidene)-2-aminobenzylamine.

Structure description top

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).

Computing details top

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 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. ORTEP view of the unique part of the compound, drawn with 50% probability displacement ellipsoids for the non-H atoms.
	Fig. 2. Packing diagram of the compound viewed along a axis.

2-Ethoxy-6-({2-[(3-ethoxy-2-hydroxybenzylidene)amino]benzyl}iminomethyl)phenol top

Crystal data top

C₂₅H₂₆N₂O₄	F(000) = 888
M_r = 418.48	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0493P)² + 0.3451P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3833 reflections	Δρ_max = 0.13 e Å⁻³
291 parameters	Δρ_min = −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)

Crystal data top

C₂₅H₂₆N₂O₄	V = 2182.6 (3) Å³
M_r = 418.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.8315 (4) Å	µ = 0.09 mm⁻¹
b = 17.5414 (14) Å	T = 296 K
c = 25.828 (2) Å	0.40 × 0.20 × 0.20 mm
β = 94.356 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3833 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2543 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.983	R_int = 0.044
32150 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	2 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.13 e Å⁻³
3833 reflections	Δρ_min = −0.13 e Å⁻³
291 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	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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₅H₂₆N₂O₄
M_r	418.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	4.8315 (4), 17.5414 (14), 25.828 (2)
β (°)	94.356 (3)
V (Å³)	2182.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.979, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	32150, 3833, 2543
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.112, 1.05
No. of reflections	3833
No. of parameters	291
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.13

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···N1	0.8502 (11)	1.794 (12)	2.5711 (19)	151 (2)
O3—H3O···N2	0.8501 (11)	1.803 (12)	2.5844 (19)	152 (2)

Acknowledgements

The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India, for providing the single-crystal X-ray diffraction data. MRPK, KUA and SSS thank the Defence Research Development Organization, New Delhi, India, for financial support. JMJ thanks the Council of Scientific and Industrial Research, New Delhi, India, for a Senior Research Fellowship.

References

Aslantaş, M., Tümer, M., Şahin, E. & Tümer, F. (2007). Acta Cryst. E63, o644–o645. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cozzi, P. G. (2004). Chem. Soc. Rev. 33, 410–421. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hodnett, E. M. & Dunn, W. J. (1970). J. Med. Chem. 13, 768–770. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tümer, M. (2000). Synth. React. Inorg. Met. Org. Chem. 30, 1139–1158. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

2-Eth­­oxy-6-({2-[(3-eth­­oxy-2-hy­dr­oxy­benzyl­­idene)amino]­benz­yl}imino­meth­yl)phenol

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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organic compounds

2-Ethoxy-6-({2-[(3-ethoxy-2-hydroxybenzylidene)amino]benzyl}iminomethyl)phenol