2-{(1E)-1-[(3-{(E)-[1-(2-Hy-droxy-4-meth-oxy-phen-yl)ethyl-idene]amino}-2,2-di-methyl-prop-yl)imino]-eth-yl}-5-meth-oxy-phenol.

Mol-ecules of the title compound, C(23)H(30)N(2)O(4), are located on a crystallographic mirror plane. The mol-ecule has a curved shape with the dihedral angle formed between the two benzene rings being 55.26 (5)°. Intra-molecular O-H⋯N hydrogen bonds are noted. In the crystal, supra-molecular layers are formed in the ac plane owing to the presence of C-H⋯π inter-actions.

Related literature

For our previous work on Schiff base complexes, see: Rayati et al. (2007 ▶, 2010 ▶).

Experimental

Crystal data

C23H30N2O4

M = 398.49

Orthorhombic,

a = 10.0764 (7) Å

b = 36.069 (2) Å

c = 5.8322 (4) Å

V = 2119.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 294 K

0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.793, T max = 1.000

6816 measured reflections

2419 independent reflections

1952 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.155

S = 1.08

2419 reflections

141 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811038815/bt5648sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038815/bt5648Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811038815/bt5648Isup3.cml

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

C23H30N2O4	F(000) = 856
Mr = 398.49	Dx = 1.249 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 2488 reflections
a = 10.0764 (7) Å	θ = 2.3–27.5°
b = 36.069 (2) Å	µ = 0.09 mm−1
c = 5.8322 (4) Å	T = 294 K
V = 2119.7 (2) Å3	Prism, yellow
Z = 4	0.30 × 0.25 × 0.20 mm

Agilent SuperNova Dual diffractometer with Atlas detector	2419 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1952 reflections with I > 2σ(I)
Mirror	Rint = 0.039
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 3.4°
ω scan	h = −9→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −33→46
Tmin = 0.793, Tmax = 1.000	l = −5→7
6816 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0642P)2 + 0.9075P] where P = (Fo2 + 2Fc2)/3
2419 reflections	(Δ/σ)max = 0.001
141 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.18 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	Occ. (<1)
O1	0.30246 (15)	0.64954 (4)	0.1933 (2)	0.0531 (4)
H1	0.354 (3)	0.6654 (8)	0.256 (6)	0.122 (13)*
O2	0.13785 (15)	0.53184 (4)	0.4322 (3)	0.0574 (4)
N1	0.46777 (15)	0.68176 (4)	0.4452 (3)	0.0419 (4)
C1	0.39243 (16)	0.62163 (5)	0.5332 (3)	0.0352 (4)
C2	0.30646 (17)	0.62129 (5)	0.3409 (3)	0.0372 (4)
C3	0.22205 (18)	0.59119 (5)	0.3013 (3)	0.0409 (4)
H3	0.1682	0.5908	0.1719	0.049*
C4	0.21869 (18)	0.56202 (5)	0.4543 (3)	0.0422 (4)
C5	0.3005 (2)	0.56209 (5)	0.6471 (3)	0.0477 (5)
H5	0.2975	0.5425	0.7506	0.057*
C6	0.38514 (19)	0.59118 (5)	0.6829 (3)	0.0436 (4)
H6	0.4399	0.5908	0.8112	0.052*
C7	0.0463 (2)	0.53147 (6)	0.2451 (5)	0.0660 (6)
H7A	−0.0043	0.5089	0.2490	0.099*
H7B	0.0942	0.5329	0.1031	0.099*
H7C	−0.0125	0.5523	0.2576	0.099*
C8	0.47861 (17)	0.65354 (5)	0.5787 (3)	0.0360 (4)
C9	0.5749 (2)	0.65215 (6)	0.7746 (4)	0.0538 (5)
H9A	0.6438	0.6701	0.7504	0.081*
H9B	0.6134	0.6278	0.7836	0.081*
H9C	0.5293	0.6576	0.9151	0.081*
C10	0.54167 (19)	0.71600 (5)	0.4786 (4)	0.0460 (5)
H10A	0.6219	0.7153	0.3869	0.055*
H10B	0.5674	0.7181	0.6384	0.055*
C11	0.4589 (2)	0.7500	0.4108 (4)	0.0342 (5)
C12	0.4327 (3)	0.7500	0.1527 (4)	0.0441 (6)
H12A	0.5157	0.7500	0.0719	0.066*
H12B	0.3830	0.7717	0.1121	0.066*	0.50
H12C	0.3830	0.7283	0.1121	0.066*	0.50
C13	0.3269 (3)	0.7500	0.5407 (5)	0.0493 (7)
H13A	0.3437	0.7500	0.7027	0.074*
H13B	0.2770	0.7283	0.5005	0.074*	0.50
H13C	0.2770	0.7717	0.5005	0.074*	0.50

	U11	U22	U33	U12	U13	U23
O1	0.0641 (9)	0.0448 (7)	0.0504 (8)	−0.0113 (7)	−0.0195 (7)	0.0126 (6)
O2	0.0598 (9)	0.0403 (7)	0.0721 (10)	−0.0103 (7)	−0.0096 (8)	0.0061 (7)
N1	0.0415 (8)	0.0358 (7)	0.0482 (8)	−0.0012 (6)	−0.0100 (7)	0.0021 (6)
C1	0.0334 (8)	0.0348 (8)	0.0375 (8)	0.0061 (7)	0.0004 (7)	−0.0005 (7)
C2	0.0387 (9)	0.0364 (8)	0.0365 (8)	0.0052 (7)	−0.0004 (7)	0.0000 (7)
C3	0.0405 (9)	0.0397 (9)	0.0425 (9)	0.0020 (8)	−0.0043 (8)	−0.0016 (7)
C4	0.0394 (9)	0.0352 (9)	0.0518 (10)	0.0020 (8)	0.0028 (8)	−0.0021 (8)
C5	0.0526 (11)	0.0398 (9)	0.0507 (10)	0.0033 (9)	−0.0001 (9)	0.0104 (8)
C6	0.0434 (10)	0.0439 (9)	0.0435 (9)	0.0057 (8)	−0.0071 (8)	0.0054 (8)
C7	0.0645 (14)	0.0506 (11)	0.0829 (16)	−0.0150 (11)	−0.0162 (13)	−0.0018 (12)
C8	0.0310 (8)	0.0375 (8)	0.0396 (8)	0.0071 (7)	−0.0012 (7)	−0.0025 (7)
C9	0.0536 (12)	0.0484 (10)	0.0594 (12)	0.0001 (9)	−0.0215 (10)	0.0064 (9)
C10	0.0389 (10)	0.0398 (9)	0.0594 (11)	−0.0008 (8)	−0.0164 (9)	0.0033 (8)
C11	0.0301 (11)	0.0377 (12)	0.0348 (11)	0.000	−0.0039 (9)	0.000
C12	0.0476 (14)	0.0482 (14)	0.0366 (12)	0.000	−0.0019 (11)	0.000
C13	0.0399 (14)	0.0658 (18)	0.0422 (14)	0.000	0.0010 (11)	0.000

O1—C2	1.334 (2)	C7—H7C	0.9600
O1—H1	0.857 (10)	C8—C9	1.500 (2)
O2—C4	1.366 (2)	C9—H9A	0.9600
O2—C7	1.429 (3)	C9—H9B	0.9600
N1—C8	1.286 (2)	C9—H9C	0.9600
N1—C10	1.455 (2)	C10—C11	1.535 (2)
C1—C6	1.405 (2)	C10—H10A	0.9700
C1—C2	1.417 (2)	C10—H10B	0.9700
C1—C8	1.466 (2)	C11—C12	1.528 (3)
C2—C3	1.399 (2)	C11—C13	1.531 (3)
C3—C4	1.380 (3)	C11—C10i	1.535 (2)
C3—H3	0.9300	C12—H12A	0.9600
C4—C5	1.394 (3)	C12—H12B	0.9600
C5—C6	1.369 (3)	C12—H12C	0.9600
C5—H5	0.9300	C13—H13A	0.9600
C6—H6	0.9300	C13—H13B	0.9600
C7—H7A	0.9600	C13—H13C	0.9600
C7—H7B	0.9600
C2—O1—H1	103 (3)	C8—C9—H9A	109.5
C4—O2—C7	117.70 (16)	C8—C9—H9B	109.5
C8—N1—C10	123.15 (15)	H9A—C9—H9B	109.5
C6—C1—C2	116.94 (16)	C8—C9—H9C	109.5
C6—C1—C8	122.15 (16)	H9A—C9—H9C	109.5
C2—C1—C8	120.81 (15)	H9B—C9—H9C	109.5
O1—C2—C3	117.90 (15)	N1—C10—C11	111.42 (14)
O1—C2—C1	121.50 (16)	N1—C10—H10A	109.3
C3—C2—C1	120.60 (16)	C11—C10—H10A	109.3
C4—C3—C2	120.01 (17)	N1—C10—H10B	109.3
C4—C3—H3	120.0	C11—C10—H10B	109.3
C2—C3—H3	120.0	H10A—C10—H10B	108.0
O2—C4—C3	124.15 (17)	C12—C11—C13	109.7 (2)
O2—C4—C5	115.47 (16)	C12—C11—C10	110.34 (14)
C3—C4—C5	120.38 (17)	C13—C11—C10	110.17 (14)
C6—C5—C4	119.53 (17)	C12—C11—C10i	110.34 (14)
C6—C5—H5	120.2	C13—C11—C10i	110.17 (14)
C4—C5—H5	120.2	C10—C11—C10i	106.04 (19)
C5—C6—C1	122.50 (17)	C11—C12—H12A	109.5
C5—C6—H6	118.8	C11—C12—H12B	109.5
C1—C6—H6	118.8	H12A—C12—H12B	109.5
O2—C7—H7A	109.5	C11—C12—H12C	109.5
O2—C7—H7B	109.5	H12A—C12—H12C	109.5
H7A—C7—H7B	109.5	H12B—C12—H12C	109.5
O2—C7—H7C	109.5	C11—C13—H13A	109.5
H7A—C7—H7C	109.5	C11—C13—H13B	109.5
H7B—C7—H7C	109.5	H13A—C13—H13B	109.5
N1—C8—C1	117.46 (15)	C11—C13—H13C	109.5
N1—C8—C9	122.87 (16)	H13A—C13—H13C	109.5
C1—C8—C9	119.67 (15)	H13B—C13—H13C	109.5
C6—C1—C2—O1	177.56 (17)	C2—C1—C6—C5	0.5 (3)
C8—C1—C2—O1	1.1 (3)	C8—C1—C6—C5	176.91 (17)
C6—C1—C2—C3	−2.0 (2)	C10—N1—C8—C1	176.40 (16)
C8—C1—C2—C3	−178.41 (16)	C10—N1—C8—C9	−3.9 (3)
O1—C2—C3—C4	−177.35 (17)	C6—C1—C8—N1	−172.62 (17)
C1—C2—C3—C4	2.2 (3)	C2—C1—C8—N1	3.6 (2)
C7—O2—C4—C3	−3.4 (3)	C6—C1—C8—C9	7.7 (3)
C7—O2—C4—C5	176.26 (19)	C2—C1—C8—C9	−176.04 (16)
C2—C3—C4—O2	178.73 (17)	C8—N1—C10—C11	−144.49 (18)
C2—C3—C4—C5	−0.9 (3)	N1—C10—C11—C12	−66.5 (2)
O2—C4—C5—C6	179.79 (17)	N1—C10—C11—C13	54.8 (2)
C3—C4—C5—C6	−0.5 (3)	N1—C10—C11—C10i	173.97 (11)
C4—C5—C6—C1	0.7 (3)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.86 (1)	1.70 (2)	2.507 (2)	157 (4)
C7—H7c···Cg1ii	0.96	2.75	3.547 (2)	141
C9—H9b···Cg1iii	0.96	2.66	3.456 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.86 (1)	1.70 (2)	2.507 (2)	157 (4)
C7—H7c⋯Cg1i	0.96	2.75	3.547 (2)	141
C9—H9b⋯Cg1ii	0.96	2.66	3.456 (2)	140

Symmetry codes: (i) ; (ii) .