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

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ISSN: 2056-9890
Volume 67| Part 5| May 2011| Page o1074

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

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[Osowle, A. A. (2008). Eur. J. Chem. 5, 130-135.]). For related structures, see: Etemadi et al. (2004[Etemadi, B., Taeb, A., Sharghi, H., Tajarodi, A. & Naeimi, H. (2004). Iran. J. Sci. Technol. Trans. A, 28, 79-83.]); Liu et al. (2010[Liu, X.-Y., Fan, Y.-H., Wang, Q., Bi, C.-F. & Wang, Y.-F. (2010). Acta Cryst. E66, o309.]); Farag et al. (2010[Farag, A. M., Teoh, S. G., Osman, H., Chantrapromma, S. & Fun, H.-K. (2010). Acta Cryst. E66, o1227-o1228.]; 2011[Farag, A. M., Teoh, S. G., Osman, H., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o143.]).

[Scheme 1]

Experimental

Crystal data
  • C28H28N2O4

  • Mr = 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.958, Tmax = 0.991

  • 9099 measured reflections

  • 2060 independent reflections

  • 1162 reflections with I > 2σ(I)

  • Rint = 0.081

Refinement
  • R[F2 > 2σ(F2)] = 0.068

  • wR(F2) = 0.224

  • S = 1.00

  • 2060 reflections

  • 155 parameters

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


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%.

Refinement top

C-bound H atoms were geometrically positioned [C—H 0.93–0.97 Å]. Atom H1A was located on a difference map, but placed in idealized position [N—H 0.86 Å]. All H atoms were refined as riding atoms, with Uiso(H) = 1.2–1.5 Uiso of the parent atom.

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
[Figure 1] 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
C28H28N2O4F(000) = 968
Mr = 456.52Dx = 1.300 Mg m3
Orthorhombic, PccaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2a 2acCell parameters from 1398 reflections
a = 44.704 (4) Åθ = 2.7–22.6°
b = 6.3576 (6) ŵ = 0.09 mm1
c = 8.2074 (9) ÅT = 298 K
V = 2332.6 (4) Å3Block, yellow
Z = 40.50 × 0.37 × 0.11 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2060 independent reflections
Radiation source: fine-focus sealed tube1162 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.081
phi and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 5328
Tmin = 0.958, Tmax = 0.991k = 77
9099 measured reflectionsl = 99
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068H-atom parameters constrained
wR(F2) = 0.224 w = 1/[σ2(Fo2) + (0.088P)2 + 3.8548P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2060 reflectionsΔρmax = 0.21 e Å3
155 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0055 (16)
Crystal data top
C28H28N2O4V = 2332.6 (4) Å3
Mr = 456.52Z = 4
Orthorhombic, PccaMo Kα radiation
a = 44.704 (4) ŵ = 0.09 mm1
b = 6.3576 (6) ÅT = 298 K
c = 8.2074 (9) Å0.50 × 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)
Tmin = 0.958, Tmax = 0.991Rint = 0.081
9099 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0680 restraints
wR(F2) = 0.224H-atom parameters constrained
S = 1.00Δρmax = 0.21 e Å3
2060 reflectionsΔρmin = 0.19 e Å3
155 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.16369 (7)0.4462 (5)0.0795 (4)0.0479 (10)
H1A0.17200.55370.12390.058*
C20.11853 (8)0.6454 (6)0.0728 (5)0.0370 (9)
O10.15974 (7)0.8123 (5)0.2021 (4)0.0628 (10)
O20.22075 (6)0.4082 (5)0.2116 (4)0.0541 (9)
C110.08741 (8)0.6581 (6)0.0253 (5)0.0388 (10)
C10.13580 (8)0.4646 (6)0.0400 (5)0.0402 (10)
H10.12660.35250.01290.048*
C60.07056 (9)0.8373 (6)0.0703 (5)0.0464 (11)
C30.13216 (10)0.8124 (6)0.1618 (5)0.0463 (11)
C100.07267 (8)0.5045 (7)0.0672 (5)0.0469 (11)
H100.08320.38610.10070.056*
C120.18209 (9)0.2620 (7)0.0560 (6)0.0505 (12)
H12A0.19410.27930.04150.061*
H12B0.16940.13970.04100.061*
C40.11373 (10)0.9880 (7)0.2060 (6)0.0557 (12)
H40.12201.09780.26570.067*
C50.08502 (10)0.9976 (7)0.1636 (5)0.0550 (12)
H50.07391.11380.19620.066*
C80.02674 (10)0.6990 (9)0.0632 (6)0.0650 (14)
H80.00670.71200.09220.078*
C70.04054 (10)0.8504 (8)0.0252 (6)0.0572 (13)
H70.02960.96770.05710.069*
C90.04327 (9)0.5238 (8)0.1096 (6)0.0553 (12)
H90.03420.41820.17030.066*
C130.20210 (9)0.2282 (7)0.1994 (6)0.0566 (13)
H13A0.19030.21150.29790.068*
H13B0.21410.10270.18400.068*
C140.24105 (8)0.4015 (7)0.3430 (5)0.0507 (12)
H14A0.25420.28080.33190.061*
H14B0.23020.38840.44490.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0378 (17)0.048 (2)0.059 (2)0.0032 (15)0.0074 (17)0.0003 (19)
C20.041 (2)0.035 (2)0.035 (2)0.0033 (17)0.0019 (18)0.0031 (18)
O10.066 (2)0.0485 (19)0.074 (2)0.0125 (15)0.0256 (18)0.0002 (17)
O20.0413 (15)0.064 (2)0.057 (2)0.0092 (14)0.0097 (14)0.0128 (16)
C110.042 (2)0.042 (2)0.032 (2)0.0007 (18)0.0030 (18)0.0051 (19)
C10.039 (2)0.042 (2)0.040 (2)0.0059 (17)0.0017 (19)0.0059 (19)
C60.054 (2)0.043 (2)0.043 (3)0.000 (2)0.007 (2)0.004 (2)
C30.059 (3)0.037 (2)0.043 (3)0.006 (2)0.005 (2)0.004 (2)
C100.043 (2)0.050 (2)0.049 (3)0.003 (2)0.004 (2)0.003 (2)
C120.040 (2)0.054 (3)0.057 (3)0.000 (2)0.003 (2)0.003 (2)
C40.081 (3)0.041 (2)0.046 (3)0.011 (3)0.004 (3)0.002 (2)
C50.074 (3)0.043 (3)0.049 (3)0.006 (2)0.006 (2)0.001 (2)
C80.040 (2)0.091 (4)0.064 (3)0.005 (3)0.001 (2)0.001 (3)
C70.052 (3)0.061 (3)0.059 (3)0.017 (2)0.008 (2)0.005 (3)
C90.045 (2)0.068 (3)0.053 (3)0.001 (2)0.006 (2)0.005 (3)
C130.047 (2)0.054 (3)0.069 (3)0.000 (2)0.011 (2)0.004 (3)
C140.044 (2)0.067 (3)0.042 (3)0.004 (2)0.003 (2)0.005 (2)
Geometric parameters (Å, º) top
N1—C11.294 (4)C12—C131.494 (6)
N1—C121.444 (5)C12—H12A0.9700
N1—H1A0.8600C12—H12B0.9700
C2—C11.410 (5)C4—C51.331 (6)
C2—C31.426 (5)C4—H40.9300
C2—C111.447 (5)C5—H50.9300
O1—C31.276 (5)C8—C71.354 (7)
O2—C141.410 (5)C8—C91.390 (6)
O2—C131.420 (5)C8—H80.9300
C11—C101.402 (5)C7—H70.9300
C11—C61.415 (5)C9—H90.9300
C1—H10.9300C13—H13A0.9700
C6—C71.394 (6)C13—H13B0.9700
C6—C51.429 (6)C14—C14i1.486 (8)
C3—C41.434 (6)C14—H14A0.9700
C10—C91.365 (5)C14—H14B0.9700
C10—H100.9300
C1—N1—C12126.1 (4)C5—C4—C3121.6 (4)
C1—N1—H1A117.0C5—C4—H4119.2
C12—N1—H1A117.0C3—C4—H4119.2
C1—C2—C3118.1 (3)C4—C5—C6122.9 (4)
C1—C2—C11121.4 (3)C4—C5—H5118.6
C3—C2—C11120.5 (4)C6—C5—H5118.6
C14—O2—C13114.1 (3)C7—C8—C9118.3 (4)
C10—C11—C6116.9 (4)C7—C8—H8120.8
C10—C11—C2124.0 (4)C9—C8—H8120.8
C6—C11—C2119.1 (4)C8—C7—C6122.6 (4)
N1—C1—C2123.6 (4)C8—C7—H7118.7
N1—C1—H1118.2C6—C7—H7118.7
C2—C1—H1118.2C10—C9—C8120.9 (5)
C7—C6—C11119.4 (4)C10—C9—H9119.5
C7—C6—C5122.3 (4)C8—C9—H9119.5
C11—C6—C5118.2 (4)O2—C13—C12106.9 (4)
O1—C3—C2123.1 (4)O2—C13—H13A110.3
O1—C3—C4119.3 (4)C12—C13—H13A110.3
C2—C3—C4117.6 (4)O2—C13—H13B110.3
C9—C10—C11121.9 (4)C12—C13—H13B110.3
C9—C10—H10119.1H13A—C13—H13B108.6
C11—C10—H10119.1O2—C14—C14i108.7 (3)
N1—C12—C13110.7 (4)O2—C14—H14A109.9
N1—C12—H12A109.5C14i—C14—H14A109.9
C13—C12—H12A109.5O2—C14—H14B109.9
N1—C12—H12B109.5C14i—C14—H14B109.9
C13—C12—H12B109.5H14A—C14—H14B108.3
H12A—C12—H12B108.1
C1—C2—C11—C105.6 (6)C2—C11—C10—C9179.8 (4)
C3—C2—C11—C10177.6 (4)C1—N1—C12—C13140.1 (4)
C1—C2—C11—C6175.9 (4)O1—C3—C4—C5178.5 (4)
C3—C2—C11—C60.9 (6)C2—C3—C4—C51.1 (7)
C12—N1—C1—C2177.0 (4)C3—C4—C5—C60.8 (7)
C3—C2—C1—N13.4 (6)C7—C6—C5—C4179.3 (5)
C11—C2—C1—N1179.8 (4)C11—C6—C5—C41.8 (7)
C10—C11—C6—C71.5 (6)C9—C8—C7—C60.3 (7)
C2—C11—C6—C7179.9 (4)C11—C6—C7—C81.1 (7)
C10—C11—C6—C5179.5 (4)C5—C6—C7—C8180.0 (4)
C2—C11—C6—C50.9 (6)C11—C10—C9—C80.5 (7)
C1—C2—C3—O15.5 (6)C7—C8—C9—C100.0 (7)
C11—C2—C3—O1177.7 (4)C14—O2—C13—C12179.6 (3)
C1—C2—C3—C4175.0 (4)N1—C12—C13—O261.2 (5)
C11—C2—C3—C41.8 (6)C13—O2—C14—C14i179.5 (4)
C6—C11—C10—C91.3 (6)
Symmetry code: (i) x+1/2, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.861.852.542 (5)136
C14—H14B···O2ii0.972.583.382 (5)141
C12—H12B···O1iii0.972.503.257 (5)134
Symmetry codes: (ii) x, y+1, z+1/2; (iii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC28H28N2O4
Mr456.52
Crystal system, space groupOrthorhombic, Pcca
Temperature (K)298
a, b, c (Å)44.704 (4), 6.3576 (6), 8.2074 (9)
V3)2332.6 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.50 × 0.37 × 0.11
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.958, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
9099, 2060, 1162
Rint0.081
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.224, 1.00
No. of reflections2060
No. of parameters155
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.19

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.861.852.542 (5)136
C14—H14B···O2i0.972.583.382 (5)141
C12—H12B···O1ii0.972.503.257 (5)134
Symmetry codes: (i) x, y+1, z+1/2; (ii) x, y1, z.
 

References

First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationEtemadi, B., Taeb, A., Sharghi, H., Tajarodi, A. & Naeimi, H. (2004). Iran. J. Sci. Technol. Trans. A, 28, 79–83.  CAS Google Scholar
First citationFarag, 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
First citationFarag, 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
First citationLiu, 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
First citationOsowle, A. A. (2008). Eur. J. Chem. 5, 130–135.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 5| May 2011| Page o1074
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