4,4′-(2,6-Dihydroxy­naphthalene-1,5-diyldimethyl­ene)dipyridinium bis­(per­chlorate)

Zhu, W.-F.; Xing, Z.

doi:10.1107/S1600536808015092

organic compounds

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Volume 64| Part 6| June 2008| Page o1173

doi:10.1107/S1600536808015092

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4,4′-(2,6-Dihydroxynaphthalene-1,5-diyldimethylene)dipyridinium bis(perchlorate)

Wei-Feng Zhu ^a and Zheng Xing ^a ^*

^aSchool of Materials Science and Engineering, Jiangsu University of Science and Technology, Zhenjiang, Jiangsu 212003, People's Republic of China
^*Correspondence e-mail: xingzheng0410@yahoo.com

(Received 15 May 2008; accepted 19 May 2008; online 30 May 2008)

The title compound, C₂₂H₂₀N₂O₂²⁺·2ClO₄⁻, was synthesized by the reaction of naphthalene-2,6-diol with pyridine-4-carbaldehyde, 4-picolylamine and perchloric acid. There is a centre of symmetry at the mid-point of the central C—C bond of the cation. The two pyridine rings are parallel to each other, and the dihedral angle between the naphthalene ring system and the pyridine ring is 80.68 (11)°. All the bond lengths and angles are normal. Classical intermolecular O—H⋯O and N—H⋯O hydrogen bonds connect cations and anions, forming a one-dimensional chain structure.

Related literature

For related literature, see: Fu & Zhao (2007 ); Aoki et al. (2004 ); Jacobsson & Ellervik (2002 ); Sasada et al. (2003 ); Szatmári et al. (2003 ); Szatmári et al. (2004 ); Cardellicchio et al. (1999 ). For a comparison of bond lengths and angles, see: Oloo et al. (2002 ).

Experimental

Crystal data

C₂₂H₂₀N₂O₂²⁺·2ClO₄⁻
M_r = 543.30
Monoclinic, P 2₁ /c
a = 4.9587 (4) Å
b = 13.0399 (11) Å
c = 17.8291 (16) Å
β = 96.767 (2)°
V = 1144.82 (17) Å³
Z = 2
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 296 (2) K
0.30 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.925, T_max = 0.988
6156 measured reflections
2011 independent reflections
1610 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.151
S = 1.06
2011 reflections
168 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1C⋯O2ⁱ	0.82	2.05	2.859 (4)	169
N1—H1B⋯O3ⁱⁱ	0.86	2.24	2.997 (4)	148
N1—H1B⋯O4ⁱⁱ	0.86	2.33	3.121 (5)	153
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x-1, y-1, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808015092/wn2262sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808015092/wn2262Isup2.hkl

checkCIF report

Comment top

Phenols and naphthols are an important class of compounds for the syntheses of dyes, pharmaceuticals and polymers. In particular, naphthalenediols are essential components of intelligent polymers such as engineering plastics and liquid crystalline polymers. 2,6-Naphthalenediol has attracted much attention for its chemical and physical properties as a liquid crystalline monomer material (Aoki et al., 2004; Jacobsson & Ellervik, 2002; Sasada et al., 2003). Electron-rich naphthols are also known to be good C-nucleophiles with the ability to undergo ready addition to C═N double bonds in modified Mannich condensations (Szatmári et al., 2003; Szatmári et al., 2004 and Cardellicchio et al.,1999). A similar 1,1'-binaphthyl derivative has been reported recently (Fu & Zhao, 2007).

The structure of the title compound is illustrated in Fig. 1. All the bond lengths and angles are normal (Oloo et al., 2002). The two pyridine rings are parallel to each other, and the dihedral angle between the naphthol ring system and the pyridine ring is 80.68 (11)°. The C3—C6—C7—C9 torsion angle is 82.8 (3)°. The packing diagram (Fig. 2) shows that three classical intermolecular O—H···O and N—H···O hydrogen-bonds (Table 1) link cations and anions to form a one-dimensional chain structure.

Related literature top

For related literature, see: Fu & Zhao (2007); Aoki et al. (2004); Jacobsson & Ellervik (2002); Sasada et al. (2003); Szatmári et al. (2003); Szatmári et al. (2004); Cardellicchio et al. (1999). For a comparison of bonds and angles, see: Oloo et al. (2002).

Experimental top

Naphthalene-2,6-diol (1.60 g, 10 mmol), pyridine-4-carbaldehyde (1.07 g, 10 mmol), 4-picolylamine (1.08 g, 10 mmol) and perchloric acid (3 ml) were well mixed and heated to 120°C, cooled down and 25 ml ethanol was added after TLC showed that the reaction was complete. Well dispersed by ethanol, 1.50 g white powder was collected after filtration and finally recrystallized from ethanol, yielding the yellow title compound.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry code (A): -x, -y + 1, -z.
	Fig. 2. The packing of the structure, viewed down the a axis, showing molecules connected by O—H···O and N—H···O hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonding have been omitted.

4,4'-(2,6-Dihydroxynaphthalene-1,5-diyldimethylene)dipyridinium bis(perchlorate) top

Crystal data top

C₂₂H₂₀N₂O₂²⁺·2ClO₄⁻	F(000) = 560
M_r = 543.30	D_x = 1.576 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3755 reflections
a = 4.9587 (4) Å	θ = 2.8–25.0°
b = 13.0399 (11) Å	µ = 0.35 mm⁻¹
c = 17.8291 (16) Å	T = 296 K
β = 96.767 (2)°	Tabular, yellow
V = 1144.82 (17) Å³	0.30 × 0.20 × 0.05 mm
Z = 2

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2011 independent reflections
Radiation source: fine-focus sealed tube	1610 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −5→5
T_min = 0.925, T_max = 0.988	k = −14→15
6156 measured reflections	l = −21→14

Refinement top

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0742P)² + 0.8634P] where P = (F_o² + 2F_c²)/3
2011 reflections	(Δ/σ)_max < 0.001
168 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₂H₂₀N₂O₂²⁺·2ClO₄⁻	V = 1144.82 (17) Å³
M_r = 543.30	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.9587 (4) Å	µ = 0.35 mm⁻¹
b = 13.0399 (11) Å	T = 296 K
c = 17.8291 (16) Å	0.30 × 0.20 × 0.05 mm
β = 96.767 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2011 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1610 reflections with I > 2σ(I)
T_min = 0.925, T_max = 0.988	R_int = 0.023
6156 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.07	Δρ_max = 0.46 e Å⁻³
2011 reflections	Δρ_min = −0.27 e Å⁻³
168 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	−0.1573 (8)	0.1073 (3)	0.0739 (2)	0.0616 (10)
H1A	−0.2367	0.0654	0.0352	0.074*
C2	0.0188 (7)	0.1821 (2)	0.0583 (2)	0.0529 (8)
H2A	0.0589	0.1915	0.0092	0.063*
C3	0.1388 (6)	0.2445 (2)	0.11614 (17)	0.0407 (7)
C4	0.0721 (7)	0.2263 (3)	0.18810 (19)	0.0532 (8)
H4A	0.1488	0.2662	0.2283	0.064*
C5	−0.1058 (8)	0.1501 (3)	0.2003 (2)	0.0630 (10)
H5A	−0.1492	0.1378	0.2488	0.076*
C6	0.3317 (6)	0.3289 (2)	0.10067 (18)	0.0456 (8)
H6A	0.5071	0.2991	0.0947	0.055*
H6B	0.3558	0.3746	0.1439	0.055*
C7	0.2348 (6)	0.3905 (2)	0.03090 (17)	0.0412 (7)
C8	0.3277 (6)	0.3667 (2)	−0.03634 (19)	0.0489 (8)
C9	0.0446 (6)	0.4723 (2)	0.03359 (17)	0.0390 (7)
C10	−0.0624 (6)	0.4991 (2)	0.10063 (17)	0.0462 (8)
H10A	−0.0082	0.4628	0.1447	0.055*
C11	−0.2443 (7)	0.5773 (3)	0.10207 (19)	0.0531 (8)
H11A	−0.3133	0.5936	0.1469	0.080*
Cl1	0.28576 (17)	0.89190 (6)	0.17150 (5)	0.0565 (3)
N1	−0.2164 (6)	0.0937 (2)	0.1433 (2)	0.0618 (8)
H1B	−0.3305	0.0466	0.1518	0.093*
O1	0.5047 (5)	0.2863 (2)	−0.03716 (15)	0.0732 (8)
H1C	0.5186	0.2701	−0.0810	0.110*
O2	0.3960 (6)	0.79156 (19)	0.18131 (15)	0.0704 (8)
O3	0.3505 (7)	0.9360 (2)	0.10369 (15)	0.0823 (9)
O4	0.4082 (10)	0.9556 (3)	0.22951 (18)	0.1228 (15)
O5	0.0089 (7)	0.8878 (3)	0.1717 (4)	0.177 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.072 (2)	0.0445 (19)	0.065 (2)	0.0003 (17)	−0.007 (2)	−0.0014 (17)
C2	0.066 (2)	0.0429 (18)	0.0483 (19)	0.0033 (15)	−0.0006 (17)	0.0020 (15)
C3	0.0432 (16)	0.0336 (15)	0.0431 (17)	0.0128 (12)	−0.0042 (13)	0.0051 (13)
C4	0.063 (2)	0.0491 (19)	0.0459 (19)	0.0051 (16)	−0.0017 (16)	−0.0011 (15)
C5	0.075 (3)	0.058 (2)	0.058 (2)	0.0047 (19)	0.015 (2)	0.0109 (18)
C6	0.0447 (17)	0.0406 (16)	0.0491 (19)	0.0056 (13)	−0.0049 (14)	0.0010 (14)
C7	0.0426 (16)	0.0362 (15)	0.0432 (17)	0.0003 (13)	−0.0020 (13)	0.0031 (13)
C8	0.0473 (18)	0.0421 (17)	0.057 (2)	0.0121 (14)	0.0068 (15)	0.0009 (15)
C9	0.0389 (15)	0.0347 (15)	0.0428 (17)	0.0008 (12)	0.0025 (13)	0.0038 (12)
C10	0.0540 (18)	0.0444 (17)	0.0403 (17)	0.0031 (14)	0.0057 (15)	0.0070 (14)
C11	0.061 (2)	0.0542 (19)	0.0453 (19)	0.0124 (16)	0.0133 (16)	0.0009 (15)
Cl1	0.0550 (5)	0.0464 (5)	0.0695 (6)	0.0110 (4)	0.0128 (4)	0.0129 (4)
N1	0.0591 (18)	0.0398 (16)	0.086 (2)	0.0005 (13)	0.0067 (17)	0.0113 (16)
O1	0.0863 (18)	0.0700 (17)	0.0639 (16)	0.0429 (14)	0.0108 (14)	0.0016 (13)
O2	0.0823 (18)	0.0523 (15)	0.0787 (18)	0.0170 (13)	0.0176 (14)	0.0166 (13)
O3	0.114 (2)	0.0672 (17)	0.0640 (18)	−0.0037 (16)	0.0037 (16)	0.0161 (14)
O4	0.225 (5)	0.077 (2)	0.064 (2)	0.008 (3)	0.010 (2)	−0.0115 (17)
O5	0.059 (2)	0.121 (3)	0.360 (7)	0.031 (2)	0.062 (3)	0.132 (4)

Geometric parameters (Å, º) top

C1—N1	1.318 (5)	C7—C9	1.429 (4)
C1—C2	1.359 (5)	C8—O1	1.369 (4)
C1—H1A	0.9300	C8—C11ⁱ	1.401 (5)
C2—C3	1.391 (4)	C9—C10	1.408 (4)
C2—H2A	0.9300	C9—C9ⁱ	1.424 (6)
C3—C4	1.383 (4)	C10—C11	1.364 (4)
C3—C6	1.504 (4)	C10—H10A	0.9300
C4—C5	1.363 (5)	C11—C8ⁱ	1.401 (5)
C4—H4A	0.9300	C11—H11A	0.9300
C5—N1	1.320 (5)	Cl1—O5	1.374 (3)
C5—H5A	0.9300	Cl1—O4	1.407 (4)
C6—C7	1.511 (4)	Cl1—O3	1.409 (3)
C6—H6A	0.9700	Cl1—O2	1.421 (3)
C6—H6B	0.9700	N1—H1B	0.8600
C7—C8	1.370 (4)	O1—H1C	0.8200

N1—C1—C2	120.5 (3)	C9—C7—C6	121.1 (3)
N1—C1—H1A	119.7	O1—C8—C7	117.7 (3)
C2—C1—H1A	119.7	O1—C8—C11ⁱ	121.1 (3)
C1—C2—C3	119.9 (3)	C7—C8—C11ⁱ	121.2 (3)
C1—C2—H2A	120.1	C10—C9—C9ⁱ	118.5 (3)
C3—C2—H2A	120.1	C10—C9—C7	122.0 (3)
C4—C3—C2	117.3 (3)	C9ⁱ—C9—C7	119.5 (3)
C4—C3—C6	121.5 (3)	C11—C10—C9	121.2 (3)
C2—C3—C6	121.2 (3)	C11—C10—H10A	119.4
C5—C4—C3	120.2 (3)	C9—C10—H10A	119.4
C5—C4—H4A	119.9	C10—C11—C8ⁱ	120.3 (3)
C3—C4—H4A	119.9	C10—C11—H11A	119.8
N1—C5—C4	120.1 (4)	C8ⁱ—C11—H11A	119.8
N1—C5—H5A	119.9	O5—Cl1—O4	111.5 (3)
C4—C5—H5A	119.9	O5—Cl1—O3	110.3 (3)
C3—C6—C7	113.1 (2)	O4—Cl1—O3	105.5 (2)
C3—C6—H6A	109.0	O5—Cl1—O2	109.5 (2)
C7—C6—H6A	109.0	O4—Cl1—O2	109.1 (2)
C3—C6—H6B	109.0	O3—Cl1—O2	110.97 (17)
C7—C6—H6B	109.0	C1—N1—C5	122.0 (3)
H6A—C6—H6B	107.8	C1—N1—H1B	119.0
C8—C7—C9	119.3 (3)	C5—N1—H1B	119.0
C8—C7—C6	119.6 (3)	C8—O1—H1C	109.5

N1—C1—C2—C3	0.3 (5)	C9—C7—C8—C11ⁱ	1.5 (5)
C1—C2—C3—C4	0.4 (4)	C6—C7—C8—C11ⁱ	−179.4 (3)
C1—C2—C3—C6	−179.2 (3)	C8—C7—C9—C10	178.7 (3)
C2—C3—C4—C5	−0.3 (5)	C6—C7—C9—C10	−0.4 (4)
C6—C3—C4—C5	179.2 (3)	C8—C7—C9—C9ⁱ	−0.1 (5)
C3—C4—C5—N1	−0.4 (5)	C6—C7—C9—C9ⁱ	−179.2 (3)
C4—C3—C6—C7	−135.8 (3)	C9ⁱ—C9—C10—C11	−1.1 (5)
C2—C3—C6—C7	43.7 (4)	C7—C9—C10—C11	−179.9 (3)
C3—C6—C7—C8	−96.3 (3)	C9—C10—C11—C8ⁱ	−0.3 (5)
C3—C6—C7—C9	82.8 (3)	C2—C1—N1—C5	−1.1 (5)
C9—C7—C8—O1	−178.5 (3)	C4—C5—N1—C1	1.1 (5)
C6—C7—C8—O1	0.6 (5)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···O2ⁱⁱ	0.82	2.05	2.859 (4)	169
N1—H1B···O3ⁱⁱⁱ	0.86	2.24	2.997 (4)	148
N1—H1B···O4ⁱⁱⁱ	0.86	2.33	3.121 (5)	153

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

Experimental details

Crystal data
Chemical formula	C₂₂H₂₀N₂O₂²⁺·2ClO₄⁻
M_r	543.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	4.9587 (4), 13.0399 (11), 17.8291 (16)
β (°)	96.767 (2)
V (Å³)	1144.82 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.30 × 0.20 × 0.05

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.925, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	6156, 2011, 1610
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.151, 1.07
No. of reflections	2011
No. of parameters	168
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.27

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···O2ⁱ	0.82	2.05	2.859 (4)	168.9
N1—H1B···O3ⁱⁱ	0.86	2.24	2.997 (4)	147.5
N1—H1B···O4ⁱⁱ	0.86	2.33	3.121 (5)	153.0

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

Acknowledgements

This project was supported by a Start-up Grant from Southeast University to Dr Zhi-Rong Qu and by Jiangsu Education Department of China (No. 05KJB350031). The data collection was carried out by the School of Chemistry and Chemical Engineering, Nanjing University, P. R. China.

References

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

4,4′-(2,6-Di­hydroxy­naphthalene-1,5-diyldi­methyl­ene)dipyridinium bis­­(per­chlorate)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4,4′-(2,6-Dihydroxynaphthalene-1,5-diyldimethylene)dipyridinium bis(perchlorate)