2,2'-{1,1'-[Pentane-1,5-diylbis(oxy-nitrilo)]diethylidyne}di-1-naphthol.

The title compound, C(29)H(30)N(2)O(4), adopts a distorted Z configuration with respect to the oxime group, which is almost coplanar with the adjacent naphthalene ring [dihedral angle = 4.11 (2)°]. There is one half-mol-ecule in the asymmetric unit, with a crystallographic twofold rotation axis passing through the central C atom of the -CH=N-O-(CH)(5)-O-N=CH- bridge. Within the mol-ecule, the dihedral angle formed by the two naphthalene rings is 79.08 (3)°, and there are two intra-molecular O-H⋯N hydrogen bonds.

Related literature

The condensation of primary amines with active carbonyl compounds can yield Schiff bases, see: Atwood & Harvey (2001 ▶); Casellato & Vigato (1977 ▶). For related structures, see: Dong et al. (2008a ▶,b ▶,c ▶, 2009 ▶); Shi et al. (2007 ▶); Yeap et al. (2008 ▶).

Experimental

Crystal data

C29H30N2O4

M = 470.55

Monoclinic,

a = 14.0683 (12) Å

b = 4.5659 (7) Å

c = 19.048 (2) Å

β = 97.321 (1)°

V = 1213.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.49 × 0.45 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.959, T max = 0.982

3170 measured reflections

1218 independent reflections

814 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.111

S = 1.02

1218 reflections

159 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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/S1600536809016584/at2776sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016584/at2776Isup2.hkl

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

C29H30N2O4	F(000) = 500
Mr = 470.55	Dx = 1.288 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 907 reflections
a = 14.0683 (12) Å	θ = 2.9–22.5°
b = 4.5659 (7) Å	µ = 0.09 mm−1
c = 19.048 (2) Å	T = 298 K
β = 97.321 (1)°	Block-like, yellow
V = 1213.6 (2) Å3	0.49 × 0.45 × 0.21 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	1218 independent reflections
Radiation source: fine-focus sealed tube	814 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→9
Tmin = 0.959, Tmax = 0.982	k = −5→5
3170 measured reflections	l = −21→22

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.057P)2] where P = (Fo2 + 2Fc2)/3
1218 reflections	(Δ/σ)max < 0.001
159 parameters	Δρmax = 0.11 e Å−3
1 restraint	Δρmin = −0.13 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	Occ. (<1)
N1	0.2185 (2)	−0.0996 (7)	0.16024 (12)	0.0654 (8)
O1	0.24369 (16)	−0.2609 (7)	0.10176 (10)	0.0807 (7)
O2	0.09872 (13)	0.1007 (6)	0.23812 (10)	0.0734 (7)
H2	0.1157	0.0056	0.2054	0.110*
C1	0.1626 (2)	−0.4239 (10)	0.07147 (17)	0.0768 (10)
H1A	0.1376	−0.5343	0.1086	0.092*
H1B	0.1829	−0.5633	0.0379	0.092*
C2	0.0834 (2)	−0.2382 (10)	0.03427 (15)	0.0700 (9)
H2A	0.1085	−0.1218	−0.0018	0.084*
H2B	0.0606	−0.1049	0.0681	0.084*
C3	0.0000	−0.4226 (13)	0.0000	0.0661 (13)
H3A	−0.0223	−0.5478	0.0357	0.079*	0.50
H3B	0.0223	−0.5478	−0.0357	0.079*	0.50
C4	0.3854 (2)	0.0583 (12)	0.16832 (16)	0.0890 (13)
H4A	0.3863	−0.0668	0.1279	0.134*
H4B	0.4321	−0.0087	0.2061	0.134*
H4C	0.4004	0.2552	0.1559	0.134*
C5	0.2876 (2)	0.0510 (9)	0.19192 (15)	0.0621 (9)
C6	0.1752 (2)	0.2479 (9)	0.27207 (14)	0.0543 (8)
C7	0.2658 (2)	0.2281 (8)	0.25198 (13)	0.0527 (8)
C8	0.3400 (2)	0.3899 (9)	0.29307 (16)	0.0673 (10)
H8	0.4022	0.3771	0.2816	0.081*
C9	0.3230 (2)	0.5610 (10)	0.34806 (16)	0.0710 (10)
H9	0.3731	0.6660	0.3728	0.085*
C10	0.2308 (2)	0.5826 (8)	0.36834 (14)	0.0575 (8)
C11	0.1552 (2)	0.4251 (8)	0.32992 (14)	0.0533 (7)
C12	0.0631 (2)	0.4448 (10)	0.35059 (15)	0.0704 (10)
H12	0.0128	0.3420	0.3255	0.084*
C13	0.0467 (3)	0.6102 (10)	0.40623 (17)	0.0794 (11)
H13	−0.0145	0.6170	0.4198	0.095*
C14	0.1205 (3)	0.7717 (11)	0.44378 (16)	0.0804 (11)
H14	0.1083	0.8883	0.4817	0.097*
C15	0.2101 (3)	0.7583 (10)	0.42496 (17)	0.0722 (10)
H15	0.2589	0.8676	0.4501	0.087*

	U11	U22	U33	U12	U13	U23
N1	0.0693 (18)	0.071 (2)	0.0551 (13)	0.0114 (18)	0.0037 (13)	0.0008 (16)
O1	0.0745 (15)	0.0976 (19)	0.0678 (13)	0.0151 (17)	0.0001 (12)	−0.0131 (16)
O2	0.0503 (12)	0.0963 (19)	0.0721 (13)	−0.0068 (14)	0.0014 (10)	−0.0109 (14)
C1	0.090 (2)	0.067 (2)	0.0693 (19)	0.015 (3)	−0.0063 (19)	−0.006 (2)
C2	0.080 (2)	0.066 (2)	0.0609 (17)	0.006 (2)	−0.0040 (16)	−0.003 (2)
C3	0.081 (3)	0.061 (3)	0.057 (2)	0.000	0.012 (2)	0.000
C4	0.066 (2)	0.132 (4)	0.071 (2)	0.001 (3)	0.0156 (17)	−0.012 (3)
C5	0.0552 (19)	0.077 (2)	0.0519 (17)	0.010 (2)	−0.0001 (15)	0.0130 (19)
C6	0.0465 (17)	0.065 (2)	0.0489 (15)	0.0020 (19)	−0.0041 (13)	0.0072 (18)
C7	0.0489 (18)	0.062 (2)	0.0458 (15)	0.0028 (18)	−0.0001 (13)	0.0135 (17)
C8	0.0472 (18)	0.088 (3)	0.0649 (19)	−0.006 (2)	0.0019 (15)	0.007 (2)
C9	0.054 (2)	0.090 (3)	0.0660 (19)	−0.014 (2)	−0.0010 (16)	0.000 (2)
C10	0.0544 (18)	0.065 (2)	0.0518 (16)	0.0001 (19)	0.0018 (15)	0.0119 (19)
C11	0.0501 (17)	0.060 (2)	0.0490 (15)	0.0016 (17)	0.0035 (13)	0.0130 (18)
C12	0.055 (2)	0.095 (3)	0.0608 (18)	−0.001 (2)	0.0049 (15)	0.001 (2)
C13	0.067 (2)	0.100 (3)	0.073 (2)	0.008 (2)	0.0121 (19)	0.002 (2)
C14	0.089 (3)	0.090 (3)	0.0620 (19)	0.008 (3)	0.011 (2)	−0.003 (2)
C15	0.074 (2)	0.077 (3)	0.0620 (18)	−0.009 (2)	−0.0031 (17)	0.004 (2)

N1—C5	1.278 (4)	C5—C7	1.465 (5)
N1—O1	1.417 (3)	C6—C7	1.380 (4)
O1—C1	1.422 (4)	C6—C11	1.424 (4)
O2—C6	1.360 (3)	C7—C8	1.428 (4)
O2—H2	0.8200	C8—C9	1.352 (4)
C1—C2	1.503 (4)	C8—H8	0.9300
C1—H1A	0.9700	C9—C10	1.402 (4)
C1—H1B	0.9700	C9—H9	0.9300
C2—C3	1.522 (5)	C10—C15	1.404 (5)
C2—H2A	0.9700	C10—C11	1.410 (4)
C2—H2B	0.9700	C11—C12	1.404 (4)
C3—C2i	1.522 (5)	C12—C13	1.345 (5)
C3—H3A	0.9700	C12—H12	0.9300
C3—H3B	0.9700	C13—C14	1.395 (5)
C4—C5	1.501 (4)	C13—H13	0.9300
C4—H4A	0.9600	C14—C15	1.355 (4)
C4—H4B	0.9600	C14—H14	0.9300
C4—H4C	0.9600	C15—H15	0.9300
C5—N1—O1	113.5 (3)	O2—C6—C7	122.6 (3)
N1—O1—C1	108.8 (2)	O2—C6—C11	115.3 (2)
C6—O2—H2	109.5	C7—C6—C11	122.2 (3)
O1—C1—C2	113.8 (3)	C6—C7—C8	116.8 (3)
O1—C1—H1A	108.8	C6—C7—C5	123.1 (3)
C2—C1—H1A	108.8	C8—C7—C5	120.1 (3)
O1—C1—H1B	108.8	C9—C8—C7	122.3 (3)
C2—C1—H1B	108.8	C9—C8—H8	118.9
H1A—C1—H1B	107.7	C7—C8—H8	118.9
C1—C2—C3	112.0 (3)	C8—C9—C10	121.0 (3)
C1—C2—H2A	109.2	C8—C9—H9	119.5
C3—C2—H2A	109.2	C10—C9—H9	119.5
C1—C2—H2B	109.2	C9—C10—C15	122.8 (3)
C3—C2—H2B	109.2	C9—C10—C11	119.0 (3)
H2A—C2—H2B	107.9	C15—C10—C11	118.2 (3)
C2—C3—C2i	112.9 (5)	C12—C11—C10	119.0 (3)
C2—C3—H3A	109.0	C12—C11—C6	122.3 (3)
C2i—C3—H3A	109.0	C10—C11—C6	118.8 (3)
C2—C3—H3B	109.0	C13—C12—C11	121.0 (3)
C2i—C3—H3B	109.0	C13—C12—H12	119.5
H3A—C3—H3B	107.8	C11—C12—H12	119.5
C5—C4—H4A	109.5	C12—C13—C14	120.6 (3)
C5—C4—H4B	109.5	C12—C13—H13	119.7
H4A—C4—H4B	109.5	C14—C13—H13	119.7
C5—C4—H4C	109.5	C15—C14—C13	119.8 (4)
H4A—C4—H4C	109.5	C15—C14—H14	120.1
H4B—C4—H4C	109.5	C13—C14—H14	120.1
N1—C5—C7	116.3 (3)	C14—C15—C10	121.4 (4)
N1—C5—C4	122.8 (3)	C14—C15—H15	119.3
C7—C5—C4	120.9 (3)	C10—C15—H15	119.3
C5—N1—O1—C1	178.9 (3)	C8—C9—C10—C15	−179.8 (4)
N1—O1—C1—C2	69.9 (4)	C8—C9—C10—C11	−0.7 (5)
O1—C1—C2—C3	177.5 (2)	C9—C10—C11—C12	179.5 (3)
C1—C2—C3—C2i	176.6 (3)	C15—C10—C11—C12	−1.4 (5)
O1—N1—C5—C7	178.7 (3)	C9—C10—C11—C6	0.4 (4)
O1—N1—C5—C4	0.9 (5)	C15—C10—C11—C6	179.5 (3)
O2—C6—C7—C8	−178.8 (3)	O2—C6—C11—C12	0.3 (5)
C11—C6—C7—C8	1.3 (5)	C7—C6—C11—C12	−179.8 (3)
O2—C6—C7—C5	0.9 (5)	O2—C6—C11—C10	179.4 (3)
C11—C6—C7—C5	−179.0 (3)	C7—C6—C11—C10	−0.7 (5)
N1—C5—C7—C6	−3.4 (5)	C10—C11—C12—C13	−0.2 (5)
C4—C5—C7—C6	174.5 (4)	C6—C11—C12—C13	178.9 (3)
N1—C5—C7—C8	176.3 (3)	C11—C12—C13—C14	1.5 (6)
C4—C5—C7—C8	−5.8 (5)	C12—C13—C14—C15	−1.2 (6)
C6—C7—C8—C9	−1.6 (5)	C13—C14—C15—C10	−0.4 (6)
C5—C7—C8—C9	178.6 (3)	C9—C10—C15—C14	−179.2 (4)
C7—C8—C9—C10	1.4 (5)	C11—C10—C15—C14	1.7 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.83	2.552 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	1.83	2.552 (3)	145