2,2'-{1,1'-[Butane-1,4-diyl-bis(oxy-nitrilo)]di-ethylidyne}di-1-naphthol.

The title compound, C(28)H(28)N(2)O(4), was synthesized by the reaction of 2-acetyl-1-naphthol with 1,4-bis-(amino-oxy)butane in ethanol. The molecule, which lies about an inversion centre, adopts a linear structure, in which the oxime groups and naphthalene ring systems assume an anti conformation. The intra-molecular inter-planar distance between parallel naphthalene rings is 1.054 (3) Å. Intra-molecular O-H⋯N hydrogen bonds are formed between the oxime nitro-gen and hydr-oxy groups.

Related literature

For salen-type compounds, see: Atwood & Harvey (2001 ▶); Okabe & Oya (2000 ▶). For related structures, see: Dong et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C28H28N2O4

M = 456.52

Triclinic,

a = 6.9590 (15) Å

b = 8.6598 (18) Å

c = 10.596 (2) Å

α = 105.841 (2)°

β = 105.940 (2)°

γ = 91.689 (1)°

V = 586.9 (2) Å3

Z = 1

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.50 × 0.43 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.958, T max = 0.983

3020 measured reflections

2026 independent reflections

1350 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.173

S = 1.02

2026 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.25 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/S160053680901647X/hg2505sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901647X/hg2505Isup2.hkl

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

C28H28N2O4	Z = 1
Mr = 456.52	F(000) = 242
Triclinic, P1	Dx = 1.292 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9590 (15) Å	Cell parameters from 1246 reflections
b = 8.6598 (18) Å	θ = 2.5–27.6°
c = 10.596 (2) Å	µ = 0.09 mm−1
α = 105.841 (2)°	T = 298 K
β = 105.940 (2)°	Block, pale-yellow
γ = 91.689 (1)°	0.50 × 0.43 × 0.20 mm
V = 586.9 (2) Å3

Bruker SMART 1000 CCD area-detector diffractometer	2026 independent reflections
Radiation source: fine-focus sealed tube	1350 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.958, Tmax = 0.983	k = −9→10
3020 measured reflections	l = −12→6

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.096P)2 + 0.0813P] where P = (Fo2 + 2Fc2)/3
2026 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.24 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	0.4299 (3)	0.3289 (2)	0.31934 (16)	0.0435 (5)
O1	0.3505 (2)	0.37340 (18)	0.19981 (14)	0.0515 (5)
O2	0.7182 (2)	0.30688 (18)	0.52155 (15)	0.0505 (5)
H2	0.6665	0.3326	0.4519	0.076*
C1	0.5112 (3)	0.4251 (3)	0.1562 (2)	0.0455 (6)
H1A	0.5966	0.3396	0.1410	0.055*
H1B	0.5923	0.5189	0.2259	0.055*
C2	0.4211 (3)	0.4667 (3)	0.0252 (2)	0.0449 (6)
H2A	0.3277	0.5459	0.0400	0.054*
H2B	0.3460	0.3705	−0.0449	0.054*
C3	0.2958 (3)	0.2877 (2)	0.3702 (2)	0.0402 (5)
C4	0.0759 (3)	0.2939 (3)	0.3091 (2)	0.0627 (7)
H4A	0.0578	0.3501	0.2408	0.094*
H4B	0.0198	0.3496	0.3798	0.094*
H4C	0.0091	0.1859	0.2673	0.094*
C5	0.5732 (3)	0.2467 (2)	0.5630 (2)	0.0372 (5)
C6	0.3690 (3)	0.2344 (2)	0.49419 (19)	0.0365 (5)
C7	0.2306 (3)	0.1639 (2)	0.5453 (2)	0.0433 (5)
H7	0.0937	0.1554	0.5009	0.052*
C8	0.2912 (3)	0.1088 (2)	0.6565 (2)	0.0438 (6)
H8	0.1961	0.0608	0.6851	0.053*
C9	0.4976 (3)	0.1238 (2)	0.7294 (2)	0.0386 (5)
C10	0.6397 (3)	0.1961 (2)	0.6838 (2)	0.0370 (5)
C11	0.8449 (3)	0.2185 (3)	0.7606 (2)	0.0506 (6)
H11	0.9400	0.2668	0.7321	0.061*
C12	0.9047 (4)	0.1696 (3)	0.8761 (3)	0.0600 (7)
H12	1.0397	0.1872	0.9270	0.072*
C13	0.7640 (4)	0.0933 (3)	0.9182 (2)	0.0564 (7)
H13	0.8068	0.0574	0.9955	0.068*
C14	0.5661 (3)	0.0711 (3)	0.8475 (2)	0.0479 (6)
H14	0.4743	0.0207	0.8770	0.057*

	U11	U22	U33	U12	U13	U23
N1	0.0575 (12)	0.0489 (11)	0.0329 (9)	0.0084 (9)	0.0176 (8)	0.0215 (8)
O1	0.0585 (10)	0.0695 (11)	0.0386 (8)	0.0082 (8)	0.0167 (7)	0.0329 (7)
O2	0.0468 (9)	0.0664 (10)	0.0556 (10)	0.0120 (7)	0.0240 (7)	0.0362 (8)
C1	0.0570 (13)	0.0519 (13)	0.0402 (12)	0.0112 (10)	0.0242 (10)	0.0234 (10)
C2	0.0573 (14)	0.0482 (12)	0.0360 (12)	0.0094 (11)	0.0180 (10)	0.0188 (9)
C3	0.0498 (12)	0.0394 (11)	0.0345 (11)	0.0036 (9)	0.0159 (9)	0.0121 (9)
C4	0.0544 (15)	0.0897 (19)	0.0525 (14)	0.0030 (13)	0.0111 (11)	0.0397 (13)
C5	0.0447 (12)	0.0363 (11)	0.0393 (11)	0.0080 (9)	0.0219 (9)	0.0152 (9)
C6	0.0443 (12)	0.0380 (11)	0.0313 (10)	0.0048 (9)	0.0155 (9)	0.0124 (8)
C7	0.0434 (12)	0.0523 (13)	0.0374 (11)	0.0003 (10)	0.0131 (9)	0.0178 (10)
C8	0.0487 (13)	0.0495 (13)	0.0404 (12)	−0.0015 (10)	0.0203 (10)	0.0182 (10)
C9	0.0505 (13)	0.0354 (11)	0.0375 (11)	0.0105 (9)	0.0202 (9)	0.0149 (9)
C10	0.0438 (12)	0.0367 (11)	0.0379 (11)	0.0138 (9)	0.0177 (9)	0.0157 (9)
C11	0.0466 (13)	0.0589 (14)	0.0597 (14)	0.0164 (11)	0.0218 (11)	0.0315 (11)
C12	0.0498 (14)	0.0742 (17)	0.0654 (16)	0.0220 (12)	0.0132 (12)	0.0376 (13)
C13	0.0643 (16)	0.0638 (15)	0.0534 (14)	0.0232 (12)	0.0170 (12)	0.0356 (12)
C14	0.0621 (15)	0.0493 (13)	0.0455 (13)	0.0138 (11)	0.0239 (11)	0.0262 (10)

N1—C3	1.285 (3)	C5—C10	1.427 (3)
N1—O1	1.398 (2)	C6—C7	1.423 (3)
O1—C1	1.425 (2)	C7—C8	1.357 (3)
O2—C5	1.350 (2)	C7—H7	0.9300
O2—H2	0.8200	C8—C9	1.415 (3)
C1—C2	1.503 (3)	C8—H8	0.9300
C1—H1A	0.9700	C9—C10	1.413 (3)
C1—H1B	0.9700	C9—C14	1.414 (3)
C2—C2i	1.509 (4)	C10—C11	1.414 (3)
C2—H2A	0.9700	C11—C12	1.365 (3)
C2—H2B	0.9700	C11—H11	0.9300
C3—C6	1.475 (3)	C12—C13	1.400 (3)
C3—C4	1.498 (3)	C12—H12	0.9300
C4—H4A	0.9600	C13—C14	1.354 (3)
C4—H4B	0.9600	C13—H13	0.9300
C4—H4C	0.9600	C14—H14	0.9300
C5—C6	1.394 (3)
C3—N1—O1	113.72 (17)	C5—C6—C7	117.71 (18)
N1—O1—C1	109.26 (15)	C5—C6—C3	122.01 (18)
C5—O2—H2	109.5	C7—C6—C3	120.26 (18)
O1—C1—C2	107.96 (18)	C8—C7—C6	122.4 (2)
O1—C1—H1A	110.1	C8—C7—H7	118.8
C2—C1—H1A	110.1	C6—C7—H7	118.8
O1—C1—H1B	110.1	C7—C8—C9	120.59 (19)
C2—C1—H1B	110.1	C7—C8—H8	119.7
H1A—C1—H1B	108.4	C9—C8—H8	119.7
C1—C2—C2i	112.2 (2)	C10—C9—C14	118.88 (19)
C1—C2—H2A	109.2	C10—C9—C8	118.87 (17)
C2i—C2—H2A	109.2	C14—C9—C8	122.24 (19)
C1—C2—H2B	109.2	C9—C10—C11	118.88 (18)
C2i—C2—H2B	109.2	C9—C10—C5	119.50 (18)
H2A—C2—H2B	107.9	C11—C10—C5	121.61 (19)
N1—C3—C6	116.56 (18)	C12—C11—C10	120.5 (2)
N1—C3—C4	122.53 (18)	C12—C11—H11	119.8
C6—C3—C4	120.91 (18)	C10—C11—H11	119.8
C3—C4—H4A	109.5	C11—C12—C13	120.4 (2)
C3—C4—H4B	109.5	C11—C12—H12	119.8
H4A—C4—H4B	109.5	C13—C12—H12	119.8
C3—C4—H4C	109.5	C14—C13—C12	120.6 (2)
H4A—C4—H4C	109.5	C14—C13—H13	119.7
H4B—C4—H4C	109.5	C12—C13—H13	119.7
O2—C5—C6	122.92 (17)	C13—C14—C9	120.8 (2)
O2—C5—C10	116.22 (18)	C13—C14—H14	119.6
C6—C5—C10	120.86 (18)	C9—C14—H14	119.6
C3—N1—O1—C1	176.83 (17)	C7—C8—C9—C14	178.56 (19)
N1—O1—C1—C2	178.10 (15)	C14—C9—C10—C11	−2.1 (3)
O1—C1—C2—C2i	176.3 (2)	C8—C9—C10—C11	176.85 (18)
O1—N1—C3—C6	178.15 (15)	C14—C9—C10—C5	178.64 (16)
O1—N1—C3—C4	−2.3 (3)	C8—C9—C10—C5	−2.4 (3)
O2—C5—C6—C7	177.98 (17)	O2—C5—C10—C9	−176.58 (16)
C10—C5—C6—C7	−2.5 (3)	C6—C5—C10—C9	3.8 (3)
O2—C5—C6—C3	−0.4 (3)	O2—C5—C10—C11	4.2 (3)
C10—C5—C6—C3	179.16 (17)	C6—C5—C10—C11	−175.34 (18)
N1—C3—C6—C5	7.8 (3)	C9—C10—C11—C12	0.5 (3)
C4—C3—C6—C5	−171.77 (19)	C5—C10—C11—C12	179.74 (19)
N1—C3—C6—C7	−170.53 (17)	C10—C11—C12—C13	1.5 (4)
C4—C3—C6—C7	9.9 (3)	C11—C12—C13—C14	−2.0 (4)
C5—C6—C7—C8	−0.4 (3)	C12—C13—C14—C9	0.3 (3)
C3—C6—C7—C8	178.04 (18)	C10—C9—C14—C13	1.7 (3)
C6—C7—C8—C9	1.8 (3)	C8—C9—C14—C13	−177.2 (2)
C7—C8—C9—C10	−0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.84	2.557 (2)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	1.84	2.557 (2)	145