2,2'-[1,1'-(Ethyl-enedioxy-dinitrilo)diethyl-idyne]di-1-naphthol.

The complete molecule of the title compound, C(26)H(24)N(2)O(4), is generated by a crystallographic centre of inversion. There are two intra-molecular O-H⋯N hydrogen bonds. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds result in zigzag chains.

Related literature

For the applications of Shiff base ligands, see: Calligaris & Randaccio (1987 ▶) For the applications bis­oxime derivatives of salen-type compounds, see: Sun et al. (2004 ▶); Wang et al. (2007 ▶). For related structures, see: Dong et al. (2008a ▶,b ▶,c ▶);

Experimental

Crystal data

C26H24N2O4

M = 428.47

Monoclinic,

a = 12.6682 (18) Å

b = 9.3728 (15) Å

c = 18.335 (2) Å

β = 97.478 (2)°

V = 2158.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.39 × 0.37 × 0.13 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.966, T max = 0.989

5220 measured reflections

1894 independent reflections

1027 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.122

S = 1.06

1894 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAIn class="Chemical">NT; 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 global, I. DOI: 10.1107/S1600536809022508/hg2524sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022508/hg2524Isup2.hkl

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

C26H24N2O4	F(000) = 904
Mr = 428.47	Dx = 1.318 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1610 reflections
a = 12.6682 (18) Å	θ = 2.2–26.7°
b = 9.3728 (15) Å	µ = 0.09 mm−1
c = 18.335 (2) Å	T = 298 K
β = 97.478 (2)°	Block-shaped, colorless
V = 2158.6 (5) Å3	0.39 × 0.37 × 0.13 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	1894 independent reflections
Radiation source: fine-focus sealed tube	1027 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→14
Tmin = 0.966, Tmax = 0.989	k = −11→9
5220 measured reflections	l = −18→21

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.037P)2 + 1.5505P] where P = (Fo2 + 2Fc2)/3
1894 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.15 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
N1	0.97510 (17)	0.0879 (2)	0.61829 (11)	0.0528 (6)
O1	1.04967 (14)	0.11327 (19)	0.68140 (9)	0.0610 (5)
O2	0.84279 (14)	−0.06506 (17)	0.53429 (9)	0.0620 (6)
H2	0.8831	−0.0456	0.5717	0.093*
C1	1.0479 (2)	−0.0049 (3)	0.73030 (14)	0.0567 (7)
H1A	1.1113	−0.0024	0.7661	0.068*
H1B	1.0493	−0.0929	0.7025	0.068*
C2	0.9707 (2)	0.1902 (3)	0.57048 (14)	0.0500 (7)
C3	1.0376 (2)	0.3226 (3)	0.58230 (16)	0.0714 (9)
H3A	1.0938	0.3072	0.6220	0.107*
H3B	0.9941	0.4009	0.5942	0.107*
H3C	1.0678	0.3444	0.5382	0.107*
C4	0.83740 (19)	0.0469 (3)	0.48738 (13)	0.0464 (6)
C5	0.89572 (19)	0.1710 (2)	0.50274 (12)	0.0469 (6)
C6	0.8818 (2)	0.2819 (3)	0.44918 (15)	0.0610 (8)
H6	0.9202	0.3660	0.4582	0.073*
C7	0.8146 (2)	0.2692 (3)	0.38547 (16)	0.0676 (8)
H7	0.8065	0.3454	0.3527	0.081*
C8	0.7568 (2)	0.1424 (3)	0.36816 (14)	0.0552 (7)
C9	0.7676 (2)	0.0289 (3)	0.42035 (13)	0.0490 (7)
C10	0.7106 (2)	−0.0991 (3)	0.40331 (15)	0.0632 (8)
H10	0.7163	−0.1737	0.4370	0.076*
C11	0.6470 (2)	−0.1137 (4)	0.33734 (18)	0.0774 (9)
H11	0.6097	−0.1982	0.3266	0.093*
C12	0.6378 (2)	−0.0025 (4)	0.28598 (17)	0.0794 (10)
H12	0.5957	−0.0146	0.2409	0.095*
C13	0.6896 (2)	0.1227 (4)	0.30122 (15)	0.0707 (9)
H13	0.6807	0.1966	0.2671	0.085*

	U11	U22	U33	U12	U13	U23
N1	0.0581 (14)	0.0524 (13)	0.0491 (13)	−0.0069 (11)	0.0112 (11)	−0.0060 (11)
O1	0.0618 (12)	0.0706 (13)	0.0511 (11)	−0.0170 (10)	0.0085 (9)	−0.0068 (9)
O2	0.0768 (13)	0.0463 (10)	0.0591 (12)	−0.0120 (9)	−0.0055 (10)	0.0078 (9)
C1	0.0569 (18)	0.0582 (17)	0.0548 (17)	0.0022 (13)	0.0063 (13)	−0.0011 (14)
C2	0.0553 (16)	0.0410 (14)	0.0572 (17)	−0.0059 (13)	0.0205 (13)	−0.0099 (13)
C3	0.085 (2)	0.0560 (18)	0.076 (2)	−0.0235 (16)	0.0195 (17)	−0.0080 (15)
C4	0.0559 (17)	0.0381 (14)	0.0474 (15)	0.0028 (12)	0.0152 (13)	0.0019 (12)
C5	0.0582 (16)	0.0398 (14)	0.0458 (15)	−0.0022 (13)	0.0176 (13)	−0.0033 (12)
C6	0.080 (2)	0.0431 (15)	0.0637 (19)	−0.0059 (15)	0.0249 (16)	0.0047 (14)
C7	0.086 (2)	0.0622 (19)	0.0587 (19)	0.0079 (17)	0.0262 (17)	0.0161 (15)
C8	0.0593 (18)	0.0602 (18)	0.0491 (16)	0.0143 (15)	0.0180 (14)	0.0030 (14)
C9	0.0485 (16)	0.0489 (16)	0.0509 (16)	0.0069 (13)	0.0117 (13)	−0.0021 (13)
C10	0.0617 (18)	0.0606 (18)	0.0659 (19)	−0.0008 (15)	0.0034 (16)	−0.0052 (15)
C11	0.064 (2)	0.087 (2)	0.079 (2)	−0.0027 (18)	−0.0008 (18)	−0.0190 (19)
C12	0.061 (2)	0.116 (3)	0.059 (2)	0.016 (2)	0.0015 (16)	−0.012 (2)
C13	0.065 (2)	0.094 (2)	0.0537 (19)	0.0235 (19)	0.0121 (16)	0.0088 (17)

N1—C2	1.295 (3)	C5—C6	1.425 (3)
N1—O1	1.415 (2)	C6—C7	1.358 (3)
O1—C1	1.427 (3)	C6—H6	0.9300
O2—C4	1.353 (3)	C7—C8	1.410 (4)
O2—H2	0.8200	C7—H7	0.9300
C1—C1i	1.490 (5)	C8—C13	1.412 (4)
C1—H1A	0.9700	C8—C9	1.426 (3)
C1—H1B	0.9700	C9—C10	1.413 (3)
C2—C5	1.473 (3)	C10—C11	1.370 (3)
C2—C3	1.504 (3)	C10—H10	0.9300
C3—H3A	0.9600	C11—C12	1.400 (4)
C3—H3B	0.9600	C11—H11	0.9300
C3—H3C	0.9600	C12—C13	1.355 (4)
C4—C5	1.387 (3)	C12—H12	0.9300
C4—C9	1.428 (3)	C13—H13	0.9300
C2—N1—O1	113.2 (2)	C7—C6—C5	122.5 (3)
N1—O1—C1	108.64 (18)	C7—C6—H6	118.8
C4—O2—H2	109.5	C5—C6—H6	118.8
O1—C1—C1i	112.64 (18)	C6—C7—C8	121.1 (3)
O1—C1—H1A	109.1	C6—C7—H7	119.5
C1i—C1—H1A	109.1	C8—C7—H7	119.5
O1—C1—H1B	109.1	C7—C8—C13	122.9 (3)
C1i—C1—H1B	109.1	C7—C8—C9	118.4 (2)
H1A—C1—H1B	107.8	C13—C8—C9	118.7 (3)
N1—C2—C5	116.6 (2)	C10—C9—C8	118.9 (2)
N1—C2—C3	122.7 (2)	C10—C9—C4	122.1 (2)
C5—C2—C3	120.8 (2)	C8—C9—C4	118.9 (2)
C2—C3—H3A	109.5	C11—C10—C9	120.3 (3)
C2—C3—H3B	109.5	C11—C10—H10	119.8
H3A—C3—H3B	109.5	C9—C10—H10	119.8
C2—C3—H3C	109.5	C10—C11—C12	120.5 (3)
H3A—C3—H3C	109.5	C10—C11—H11	119.8
H3B—C3—H3C	109.5	C12—C11—H11	119.8
O2—C4—C5	122.7 (2)	C13—C12—C11	120.7 (3)
O2—C4—C9	115.4 (2)	C13—C12—H12	119.7
C5—C4—C9	121.9 (2)	C11—C12—H12	119.7
C4—C5—C6	117.2 (2)	C12—C13—C8	120.9 (3)
C4—C5—C2	122.8 (2)	C12—C13—H13	119.6
C6—C5—C2	120.1 (2)	C8—C13—H13	119.6
C2—N1—O1—C1	179.8 (2)	C6—C7—C8—C9	2.2 (4)
N1—O1—C1—C1i	−75.0 (3)	C7—C8—C9—C10	−179.5 (2)
O1—N1—C2—C5	179.31 (19)	C13—C8—C9—C10	−0.1 (4)
O1—N1—C2—C3	−0.8 (3)	C7—C8—C9—C4	−0.9 (3)
O2—C4—C5—C6	−179.2 (2)	C13—C8—C9—C4	178.5 (2)
C9—C4—C5—C6	1.1 (3)	O2—C4—C9—C10	−1.9 (3)
O2—C4—C5—C2	1.7 (4)	C5—C4—C9—C10	177.9 (2)
C9—C4—C5—C2	−178.1 (2)	O2—C4—C9—C8	179.6 (2)
N1—C2—C5—C4	−4.3 (3)	C5—C4—C9—C8	−0.7 (3)
C3—C2—C5—C4	175.8 (2)	C8—C9—C10—C11	0.6 (4)
N1—C2—C5—C6	176.6 (2)	C4—C9—C10—C11	−177.9 (2)
C3—C2—C5—C6	−3.3 (4)	C9—C10—C11—C12	0.1 (4)
C4—C5—C6—C7	0.2 (4)	C10—C11—C12—C13	−1.5 (5)
C2—C5—C6—C7	179.3 (2)	C11—C12—C13—C8	2.1 (5)
C5—C6—C7—C8	−1.8 (4)	C7—C8—C13—C12	178.1 (3)
C6—C7—C8—C13	−177.2 (3)	C9—C8—C13—C12	−1.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.84	2.562 (3)	146
C10—H10···O2ii	0.93	2.63	3.446 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	1.84	2.562 (3)	146
C10—H10⋯O2i	0.93	2.63	3.446 (3)	146

Symmetry code: (i) .