2-[({2-[(2-Hy-droxy-5-meth-oxy-benzyl-idene)amino]-eth-yl}imino)-meth-yl]-4-meth-oxy-phenol.

The asymmetric unit of the title compound, C(18)H(20)N(2)O(4), contains one-half mol-ecule with an inversion center located at the centroid of the mol-ecule. In the crystal, mol-ecules are linked by C-H⋯π inter-actions, forming layers parallel to (101). An intra-molecular O-H⋯N hydrogen bond also occurs.

Related literature

For the synthesis of similar compounds see: Srinivasan et al. (1986 ▶); Moutet & Ourari (1997 ▶); Ourari et al. (2008 ▶).

Experimental

Crystal data

C18H20N2O4

M = 328.36

Monoclinic,

a = 15.0040 (12) Å

b = 5.9722 (3) Å

c = 9.3128 (8) Å

β = 92.001 (3)°

V = 833.98 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.50 × 0.23 × 0.19 mm

Data collection

Nonius KappaCCD diffractometer

3001 measured reflections

1664 independent reflections

1097 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.167

S = 1.05

1664 reflections

111 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.16 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812018405/bq2353sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018405/bq2353Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018405/bq2353Isup3.cml

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

C18H20N2O4	F(000) = 348
Mr = 328.36	Dx = 1.308 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1761 reflections
a = 15.0040 (12) Å	θ = 1.0–26.4°
b = 5.9722 (3) Å	µ = 0.09 mm−1
c = 9.3128 (8) Å	T = 295 K
β = 92.001 (3)°	Prism, colorless
V = 833.98 (11) Å3	0.50 × 0.23 × 0.19 mm
Z = 2

Nonius KappaCCD diffractometer	1097 reflections with I > 2σ(I)
Radiation source: Enraf–Nonius FR590	Rint = 0.021
Graphite monochromator	θmax = 26.4°, θmin = 2.7°
Detector resolution: 9 pixels mm-1	h = −18→18
CCD rotation images, thick slices scans	k = −6→7
3001 measured reflections	l = −11→11
1664 independent reflections

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)] = 0.054	H-atom parameters constrained
wR(F2) = 0.167	w = 1/[σ2(Fo2) + (0.101P)2 + 0.0006P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1664 reflections	Δρmax = 0.23 e Å−3
111 parameters	Δρmin = −0.16 e Å−3
0 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: 0.08 (2)

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
C1	0.00544 (12)	0.5332 (3)	0.42227 (18)	0.0554 (5)
H1A	0.0237	0.404	0.3674	0.066*
H1B	−0.0511	0.586	0.3816	0.066*
C3	0.13689 (11)	0.6835 (3)	0.32973 (18)	0.0500 (5)
H3	0.1399	0.5537	0.2749	0.06*
C4	0.20642 (11)	0.8520 (3)	0.31789 (17)	0.0488 (5)
C5	0.20521 (13)	1.0483 (3)	0.40154 (19)	0.0545 (5)
C6	0.27360 (14)	1.2037 (3)	0.3894 (2)	0.0620 (5)
H6	0.2731	1.3341	0.4439	0.074*
C7	0.34154 (14)	1.1672 (3)	0.2983 (2)	0.0623 (5)
H7	0.3863	1.2739	0.2909	0.075*
C8	0.34469 (12)	0.9719 (3)	0.21605 (18)	0.0542 (5)
C9	0.27715 (11)	0.8166 (3)	0.22553 (18)	0.0515 (5)
H9	0.2784	0.687	0.1702	0.062*
C10	0.42592 (14)	0.7497 (3)	0.0532 (3)	0.0764 (7)
H10A	0.4313	0.6263	0.119	0.115*
H10B	0.4781	0.7572	−0.0033	0.115*
H10C	0.3742	0.7287	−0.0089	0.115*
N2	0.07208 (9)	0.7091 (2)	0.41315 (16)	0.0544 (5)
O5	0.13958 (10)	1.0889 (2)	0.49361 (15)	0.0712 (5)
H5	0.1037	0.9853	0.4903	0.107*
O8	0.41724 (10)	0.9514 (2)	0.13122 (15)	0.0727 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0480 (10)	0.0591 (10)	0.0594 (11)	−0.0045 (7)	0.0065 (8)	−0.0027 (8)
C3	0.0467 (10)	0.0539 (9)	0.0494 (10)	0.0010 (7)	0.0029 (8)	−0.0004 (7)
C4	0.0494 (10)	0.0483 (9)	0.0486 (10)	0.0007 (7)	0.0001 (8)	0.0034 (6)
C5	0.0598 (12)	0.0495 (10)	0.0541 (10)	0.0057 (8)	0.0025 (9)	0.0020 (7)
C6	0.0718 (13)	0.0466 (9)	0.0672 (12)	−0.0003 (8)	−0.0038 (10)	−0.0033 (8)
C7	0.0652 (12)	0.0518 (10)	0.0696 (12)	−0.0104 (8)	−0.0025 (10)	0.0063 (9)
C8	0.0517 (11)	0.0589 (10)	0.0521 (10)	−0.0062 (7)	0.0040 (8)	0.0086 (7)
C9	0.0546 (11)	0.0514 (9)	0.0488 (10)	−0.0030 (7)	0.0044 (9)	−0.0013 (7)
C10	0.0628 (13)	0.0883 (14)	0.0793 (15)	−0.0105 (10)	0.0209 (11)	−0.0118 (11)
N2	0.0486 (9)	0.0571 (9)	0.0578 (9)	−0.0012 (6)	0.0068 (7)	−0.0004 (6)
O5	0.0726 (10)	0.0631 (8)	0.0789 (10)	0.0062 (6)	0.0182 (8)	−0.0140 (6)
O8	0.0643 (9)	0.0764 (9)	0.0786 (10)	−0.0194 (7)	0.0215 (7)	−0.0033 (7)

C1—N2	1.455 (2)	C6—H6	0.93
C1—C1i	1.515 (3)	C7—C8	1.397 (2)
C1—H1A	0.97	C7—H7	0.93
C1—H1B	0.97	C8—O8	1.373 (2)
C3—N2	1.275 (2)	C8—C9	1.379 (2)
C3—C4	1.456 (2)	C9—H9	0.93
C3—H3	0.93	C10—O8	1.415 (2)
C4—C9	1.405 (2)	C10—H10A	0.96
C4—C5	1.408 (2)	C10—H10B	0.96
C5—O5	1.350 (2)	C10—H10C	0.96
C5—C6	1.391 (3)	O5—H5	0.82
C6—C7	1.366 (3)
N2—C1—C1i	109.99 (18)	C6—C7—C8	120.91 (16)
N2—C1—H1A	109.7	C6—C7—H7	119.5
C1i—C1—H1A	109.7	C8—C7—H7	119.5
N2—C1—H1B	109.7	O8—C8—C9	125.19 (16)
C1i—C1—H1B	109.7	O8—C8—C7	115.64 (15)
H1A—C1—H1B	108.2	C9—C8—C7	119.18 (17)
N2—C3—C4	121.80 (15)	C8—C9—C4	120.69 (16)
N2—C3—H3	119.1	C8—C9—H9	119.7
C4—C3—H3	119.1	C4—C9—H9	119.7
C9—C4—C5	119.26 (16)	O8—C10—H10A	109.5
C9—C4—C3	120.03 (15)	O8—C10—H10B	109.5
C5—C4—C3	120.68 (16)	H10A—C10—H10B	109.5
O5—C5—C6	119.26 (16)	O8—C10—H10C	109.5
O5—C5—C4	121.64 (16)	H10A—C10—H10C	109.5
C6—C5—C4	119.10 (17)	H10B—C10—H10C	109.5
C7—C6—C5	120.86 (16)	C3—N2—C1	119.31 (15)
C7—C6—H6	119.6	C5—O5—H5	109.5
C5—C6—H6	119.6	C8—O8—C10	117.41 (14)
N2—C3—C4—C9	179.47 (16)	C6—C7—C8—C9	1.2 (3)
N2—C3—C4—C5	1.4 (3)	O8—C8—C9—C4	178.87 (17)
C9—C4—C5—O5	−178.94 (15)	C7—C8—C9—C4	−0.8 (3)
C3—C4—C5—O5	−0.9 (3)	C5—C4—C9—C8	−0.2 (2)
C9—C4—C5—C6	0.8 (2)	C3—C4—C9—C8	−178.27 (15)
C3—C4—C5—C6	178.82 (15)	C4—C3—N2—C1	−178.95 (15)
O5—C5—C6—C7	179.38 (17)	C1i—C1—N2—C3	127.0 (2)
C4—C5—C6—C7	−0.3 (3)	C9—C8—O8—C10	−3.6 (3)
C5—C6—C7—C8	−0.7 (3)	C7—C8—O8—C10	176.06 (17)
C6—C7—C8—O8	−178.45 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N2	0.82	1.85	2.5844 (18)	148
C10—H10C···Cgii	0.96	2.64	3.521 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯N2	0.82	1.85	2.5844 (18)	148
C10—H10C⋯Cgi	0.96	2.64	3.521 (2)	152

Symmetry code: (i) .