1,1′-[(1E,11E)-5,8-Dioxa-2,11-diazo­nia­dodeca-1,11-diene-1,12-di­yl]dinaph­thal­en-2-olate

Liu, Y.; Liu, K.; Cao, Z.; Niu, M.

doi:10.1107/S1600536811012219

organic compounds

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1,1′-[(1E,11E)-5,8-Dioxa-2,11-diazoniadodeca-1,11-diene-1,12-diyl]dinaphthalen-2-olate

Yanju Liu,^a Kai Liu,^b Zhiqiang Cao ^c and Meiju Niu ^c ^*

^aState Key Laboratory of Water Environment Simulation, School of Environment, Beijing Normal University, Beijing 100875, People's Republic of China, ^bDongchang College, Liaocheng University, Shandong 252059, People's Republic of China, and ^cCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: niumeiju@163.com

(Received 22 March 2011; accepted 1 April 2011; online 7 April 2011)

The title compound, C₂₈H₂₈N₂O₄, crystallizes in a zwitterionic form with deprotonated naphthol hydroxy groups and protonated imine N atoms. The asymmetric unit contains one half-molecule located on a twofold rotation axis. Intramolecular N—H⋯O hydrogen bonds occur and the two bicyclic ring systems form a dihedral angle of 64.2 (1)°. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link the molecules into layers parallel to the bc plane.

Related literature

For applications of Schiff bases in coordination chemistry, see: Osowle (2008 ). For related structures, see: Etemadi et al. (2004 ); Liu et al. (2010 ); Farag et al. (2010 ; 2011 ).

Experimental

Crystal data

C₂₈H₂₈N₂O₄
M_r = 456.52
Orthorhombic, P c c a
a = 44.704 (4) Å
b = 6.3576 (6) Å
c = 8.2074 (9) Å
V = 2332.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.50 × 0.37 × 0.11 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.958, T_max = 0.991
9099 measured reflections
2060 independent reflections
1162 reflections with I > 2σ(I)
R_int = 0.081

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.224
S = 1.00
2060 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.86	1.85	2.542 (5)	136
C14—H14B⋯O2ⁱ	0.97	2.58	3.382 (5)	141
C12—H12B⋯O1ⁱⁱ	0.97	2.50	3.257 (5)	134
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012219/cv5066sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811012219/cv5066Isup2.hkl

checkCIF report

Comment top

Schiff bases have various applications in coordination chemistry (Osowle, 2008). Herewith we present the title compound (I), which is a new crowned Schiff base.

In (I) (Fig. 1), all bond lengths and angles are usual and comparable with those observed in the related compounds (Etemadi et al., 2004; Liu et al., 2010; Farag et al., 2010, 2011). Each molecule is situated on a twofold rotational axis. Intramolecular N—H···O hydrogen bonds (Table 1) influence the molecular conformation - two bicycles form a dihedral angle of 64.2 (1)°. In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) link molecules into layers parallel to bc plane.

Related literature top

For applications of Schiff bases in coordination chemistry, see: Osowle (2008). For related structures, see: Etemadi et al. (2004); Liu et al. (2010); Farag et al. (2010; 2011).

Experimental top

The title compound was synthesized by adding drop-wise a solution of 3,6-dioxa-1,8-diaminooctane (1.48 g,10 mmol) in absolute methanol (10 mL) to a methanol solution (20 mL) of 2-hydroxy-1-naphthaldehyde (3.4438 g,20 mmol) under stirring at room temperature. The resultant reaction mixture was then refluxed for 5 h, cooled and concentrated under reduced pressure, and then the residue was retained at -268 K for overnight. The bright yellow crystal which suitable for X-ray analysis was formed, filtered and dried under reduced pressure.Yield:82%. Analysis found: C 73.07, H 6.06, N 6.51%; calculated for C₂₈H₂₈N₂O₄ (Mr=456.54): C 73.66, H 6.18, N 6.14%.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing the atomic labels and 30% probability displacement ellipsoids. Symmetry code: (A) -x + 1/2,-y + 1,z.

1,1'-[(1E,11E)-5,8-Dioxa-2,11-diazoniadodeca-1,11-diene-1,12-diyl]dinaphthalen-2-olate top

Crystal data top

C₂₈H₂₈N₂O₄	F(000) = 968
M_r = 456.52	D_x = 1.300 Mg m⁻³
Orthorhombic, Pcca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2a 2ac	Cell parameters from 1398 reflections
a = 44.704 (4) Å	θ = 2.7–22.6°
b = 6.3576 (6) Å	µ = 0.09 mm⁻¹
c = 8.2074 (9) Å	T = 298 K
V = 2332.6 (4) Å³	Block, yellow
Z = 4	0.50 × 0.37 × 0.11 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2060 independent reflections
Radiation source: fine-focus sealed tube	1162 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.081
phi and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −53→28
T_min = 0.958, T_max = 0.991	k = −7→7
9099 measured reflections	l = −9→9

Refinement top

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)] = 0.068	H-atom parameters constrained
wR(F²) = 0.224	w = 1/[σ²(F_o²) + (0.088P)² + 3.8548P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2060 reflections	Δρ_max = 0.21 e Å⁻³
155 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0055 (16)

Crystal data top

C₂₈H₂₈N₂O₄	V = 2332.6 (4) Å³
M_r = 456.52	Z = 4
Orthorhombic, Pcca	Mo Kα radiation
a = 44.704 (4) Å	µ = 0.09 mm⁻¹
b = 6.3576 (6) Å	T = 298 K
c = 8.2074 (9) Å	0.50 × 0.37 × 0.11 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2060 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1162 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.991	R_int = 0.081
9099 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.224	H-atom parameters constrained
S = 1.00	Δρ_max = 0.21 e Å⁻³
2060 reflections	Δρ_min = −0.19 e Å⁻³
155 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.16369 (7)	0.4462 (5)	0.0795 (4)	0.0479 (10)
H1A	0.1720	0.5537	0.1239	0.058*
C2	0.11853 (8)	0.6454 (6)	0.0728 (5)	0.0370 (9)
O1	0.15974 (7)	0.8123 (5)	0.2021 (4)	0.0628 (10)
O2	0.22075 (6)	0.4082 (5)	0.2116 (4)	0.0541 (9)
C11	0.08741 (8)	0.6581 (6)	0.0253 (5)	0.0388 (10)
C1	0.13580 (8)	0.4646 (6)	0.0400 (5)	0.0402 (10)
H1	0.1266	0.3525	−0.0129	0.048*
C6	0.07056 (9)	0.8373 (6)	0.0703 (5)	0.0464 (11)
C3	0.13216 (10)	0.8124 (6)	0.1618 (5)	0.0463 (11)
C10	0.07267 (8)	0.5045 (7)	−0.0672 (5)	0.0469 (11)
H10	0.0832	0.3861	−0.1007	0.056*
C12	0.18209 (9)	0.2620 (7)	0.0560 (6)	0.0505 (12)
H12A	0.1941	0.2793	−0.0415	0.061*
H12B	0.1694	0.1397	0.0410	0.061*
C4	0.11373 (10)	0.9880 (7)	0.2060 (6)	0.0557 (12)
H4	0.1220	1.0978	0.2657	0.067*
C5	0.08502 (10)	0.9976 (7)	0.1636 (5)	0.0550 (12)
H5	0.0739	1.1138	0.1962	0.066*
C8	0.02674 (10)	0.6990 (9)	−0.0632 (6)	0.0650 (14)
H8	0.0067	0.7120	−0.0922	0.078*
C7	0.04054 (10)	0.8504 (8)	0.0252 (6)	0.0572 (13)
H7	0.0296	0.9677	0.0571	0.069*
C9	0.04327 (9)	0.5238 (8)	−0.1096 (6)	0.0553 (12)
H9	0.0342	0.4182	−0.1703	0.066*
C13	0.20210 (9)	0.2282 (7)	0.1994 (6)	0.0566 (13)
H13A	0.1903	0.2115	0.2979	0.068*
H13B	0.2141	0.1027	0.1840	0.068*
C14	0.24105 (8)	0.4015 (7)	0.3430 (5)	0.0507 (12)
H14A	0.2542	0.2808	0.3319	0.061*
H14B	0.2302	0.3884	0.4449	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0378 (17)	0.048 (2)	0.059 (2)	−0.0032 (15)	−0.0074 (17)	0.0003 (19)
C2	0.041 (2)	0.035 (2)	0.035 (2)	−0.0033 (17)	−0.0019 (18)	0.0031 (18)
O1	0.066 (2)	0.0485 (19)	0.074 (2)	−0.0125 (15)	−0.0256 (18)	0.0002 (17)
O2	0.0413 (15)	0.064 (2)	0.057 (2)	−0.0092 (14)	−0.0097 (14)	0.0128 (16)
C11	0.042 (2)	0.042 (2)	0.032 (2)	0.0007 (18)	0.0030 (18)	0.0051 (19)
C1	0.039 (2)	0.042 (2)	0.040 (2)	−0.0059 (17)	−0.0017 (19)	0.0059 (19)
C6	0.054 (2)	0.043 (2)	0.043 (3)	0.000 (2)	0.007 (2)	0.004 (2)
C3	0.059 (3)	0.037 (2)	0.043 (3)	−0.006 (2)	−0.005 (2)	0.004 (2)
C10	0.043 (2)	0.050 (2)	0.049 (3)	−0.003 (2)	−0.004 (2)	−0.003 (2)
C12	0.040 (2)	0.054 (3)	0.057 (3)	0.000 (2)	−0.003 (2)	−0.003 (2)
C4	0.081 (3)	0.041 (2)	0.046 (3)	−0.011 (3)	−0.004 (3)	−0.002 (2)
C5	0.074 (3)	0.043 (3)	0.049 (3)	0.006 (2)	0.006 (2)	0.001 (2)
C8	0.040 (2)	0.091 (4)	0.064 (3)	0.005 (3)	−0.001 (2)	0.001 (3)
C7	0.052 (3)	0.061 (3)	0.059 (3)	0.017 (2)	0.008 (2)	0.005 (3)
C9	0.045 (2)	0.068 (3)	0.053 (3)	−0.001 (2)	−0.006 (2)	−0.005 (3)
C13	0.047 (2)	0.054 (3)	0.069 (3)	0.000 (2)	−0.011 (2)	0.004 (3)
C14	0.044 (2)	0.067 (3)	0.042 (3)	0.004 (2)	−0.003 (2)	0.005 (2)

Geometric parameters (Å, º) top

N1—C1	1.294 (4)	C12—C13	1.494 (6)
N1—C12	1.444 (5)	C12—H12A	0.9700
N1—H1A	0.8600	C12—H12B	0.9700
C2—C1	1.410 (5)	C4—C5	1.331 (6)
C2—C3	1.426 (5)	C4—H4	0.9300
C2—C11	1.447 (5)	C5—H5	0.9300
O1—C3	1.276 (5)	C8—C7	1.354 (7)
O2—C14	1.410 (5)	C8—C9	1.390 (6)
O2—C13	1.420 (5)	C8—H8	0.9300
C11—C10	1.402 (5)	C7—H7	0.9300
C11—C6	1.415 (5)	C9—H9	0.9300
C1—H1	0.9300	C13—H13A	0.9700
C6—C7	1.394 (6)	C13—H13B	0.9700
C6—C5	1.429 (6)	C14—C14ⁱ	1.486 (8)
C3—C4	1.434 (6)	C14—H14A	0.9700
C10—C9	1.365 (5)	C14—H14B	0.9700
C10—H10	0.9300

C1—N1—C12	126.1 (4)	C5—C4—C3	121.6 (4)
C1—N1—H1A	117.0	C5—C4—H4	119.2
C12—N1—H1A	117.0	C3—C4—H4	119.2
C1—C2—C3	118.1 (3)	C4—C5—C6	122.9 (4)
C1—C2—C11	121.4 (3)	C4—C5—H5	118.6
C3—C2—C11	120.5 (4)	C6—C5—H5	118.6
C14—O2—C13	114.1 (3)	C7—C8—C9	118.3 (4)
C10—C11—C6	116.9 (4)	C7—C8—H8	120.8
C10—C11—C2	124.0 (4)	C9—C8—H8	120.8
C6—C11—C2	119.1 (4)	C8—C7—C6	122.6 (4)
N1—C1—C2	123.6 (4)	C8—C7—H7	118.7
N1—C1—H1	118.2	C6—C7—H7	118.7
C2—C1—H1	118.2	C10—C9—C8	120.9 (5)
C7—C6—C11	119.4 (4)	C10—C9—H9	119.5
C7—C6—C5	122.3 (4)	C8—C9—H9	119.5
C11—C6—C5	118.2 (4)	O2—C13—C12	106.9 (4)
O1—C3—C2	123.1 (4)	O2—C13—H13A	110.3
O1—C3—C4	119.3 (4)	C12—C13—H13A	110.3
C2—C3—C4	117.6 (4)	O2—C13—H13B	110.3
C9—C10—C11	121.9 (4)	C12—C13—H13B	110.3
C9—C10—H10	119.1	H13A—C13—H13B	108.6
C11—C10—H10	119.1	O2—C14—C14ⁱ	108.7 (3)
N1—C12—C13	110.7 (4)	O2—C14—H14A	109.9
N1—C12—H12A	109.5	C14ⁱ—C14—H14A	109.9
C13—C12—H12A	109.5	O2—C14—H14B	109.9
N1—C12—H12B	109.5	C14ⁱ—C14—H14B	109.9
C13—C12—H12B	109.5	H14A—C14—H14B	108.3
H12A—C12—H12B	108.1

C1—C2—C11—C10	−5.6 (6)	C2—C11—C10—C9	−179.8 (4)
C3—C2—C11—C10	177.6 (4)	C1—N1—C12—C13	−140.1 (4)
C1—C2—C11—C6	175.9 (4)	O1—C3—C4—C5	178.5 (4)
C3—C2—C11—C6	−0.9 (6)	C2—C3—C4—C5	−1.1 (7)
C12—N1—C1—C2	177.0 (4)	C3—C4—C5—C6	−0.8 (7)
C3—C2—C1—N1	−3.4 (6)	C7—C6—C5—C4	−179.3 (5)
C11—C2—C1—N1	179.8 (4)	C11—C6—C5—C4	1.8 (7)
C10—C11—C6—C7	1.5 (6)	C9—C8—C7—C6	0.3 (7)
C2—C11—C6—C7	−179.9 (4)	C11—C6—C7—C8	−1.1 (7)
C10—C11—C6—C5	−179.5 (4)	C5—C6—C7—C8	180.0 (4)
C2—C11—C6—C5	−0.9 (6)	C11—C10—C9—C8	0.5 (7)
C1—C2—C3—O1	5.5 (6)	C7—C8—C9—C10	0.0 (7)
C11—C2—C3—O1	−177.7 (4)	C14—O2—C13—C12	179.6 (3)
C1—C2—C3—C4	−175.0 (4)	N1—C12—C13—O2	−61.2 (5)
C11—C2—C3—C4	1.8 (6)	C13—O2—C14—C14ⁱ	−179.5 (4)
C6—C11—C10—C9	−1.3 (6)

Symmetry code: (i) −x+1/2, −y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	1.85	2.542 (5)	136
C14—H14B···O2ⁱⁱ	0.97	2.58	3.382 (5)	141
C12—H12B···O1ⁱⁱⁱ	0.97	2.50	3.257 (5)	134

Symmetry codes: (ii) x, −y+1, z+1/2; (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₈H₂₈N₂O₄
M_r	456.52
Crystal system, space group	Orthorhombic, Pcca
Temperature (K)	298
a, b, c (Å)	44.704 (4), 6.3576 (6), 8.2074 (9)
V (Å³)	2332.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.37 × 0.11

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.958, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	9099, 2060, 1162
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.224, 1.00
No. of reflections	2060
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.19

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	1.85	2.542 (5)	136
C14—H14B···O2ⁱ	0.97	2.58	3.382 (5)	141
C12—H12B···O1ⁱⁱ	0.97	2.50	3.257 (5)	134

Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, y−1, z.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Etemadi, B., Taeb, A., Sharghi, H., Tajarodi, A. & Naeimi, H. (2004). Iran. J. Sci. Technol. Trans. A, 28, 79–83. CAS Google Scholar
Farag, A. M., Teoh, S. G., Osman, H., Chantrapromma, S. & Fun, H.-K. (2010). Acta Cryst. E66, o1227–o1228. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farag, A. M., Teoh, S. G., Osman, H., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o143. Web of Science CrossRef IUCr Journals Google Scholar
Liu, X.-Y., Fan, Y.-H., Wang, Q., Bi, C.-F. & Wang, Y.-F. (2010). Acta Cryst. E66, o309. Web of Science CSD CrossRef IUCr Journals Google Scholar
Osowle, A. A. (2008). Eur. J. Chem. 5, 130–135. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1,1′-[(1E,11E)-5,8-Dioxa-2,11-diazo­nia­dodeca-1,11-diene-1,12-di­yl]dinaph­thal­en-2-olate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

1,1′-[(1E,11E)-5,8-Dioxa-2,11-diazoniadodeca-1,11-diene-1,12-diyl]dinaphthalen-2-olate