2,2′-Dimethyl-7,7′-(methyl­enediimino)di-1,8-naphthyridin-1-ium bis­(perchlorate)

Mo, J.; Liu, J.-H.; Pan, Y.-S.; Zhang, S.-M.; Du, X.-D.

doi:10.1107/S1600536808024616

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1702

doi:10.1107/S1600536808024616

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RETRACTED ARTICLE

This article has been retracted. To view the retraction notice, click here.

Retracted: 2,2′-Dimethyl-7,7′-(methylenediimino)di-1,8-naphthyridin-1-ium bis(perchlorate)

Juan Mo,^a ^* Jian-Hua Liu,^a Yu-Shan Pan,^a Su-Mei Zhang ^a and Xiang-Dang Du ^a

^aCollege of Animal Husbandry and Veterinary Studies, Henan Agricultural University, Zhengzhou, Henan Province 450002, People's Republic of China
^*Correspondence e-mail: mojuan52@126.com

(Received 14 June 2008; accepted 31 July 2008; online 6 August 2008)

In the title salt, C₁₉H₂₀N₆²⁺·2ClO₄⁻, the two planar 1,8-naphthyridine systems are linked by a methylenediamine group with a dihedral angle of 60.6 (1)° between the two systems. The crystal structure involves extensive N—H⋯O and C—H⋯O hydrogen bonding.

Related literature

For related literature, see: Baker & Norman (2004 ); Gavrilova & Bosnich (2004 ); Nakatani et al. (2000 , 2001 ); Stadie et al. (2007 ); Ferrarini et al. (1997 ).

Experimental

Crystal data

C₁₉H₂₀N₆²⁺·2ClO₄⁻
M_r = 531.31
Orthorhombic, P b c a
a = 8.191 (1) Å
b = 19.325 (2) Å
c = 27.885 (2) Å
V = 4413.9 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 113 (2) K
0.34 × 0.16 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.908, T_max = 0.952
31220 measured reflections
3882 independent reflections
3598 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.134
S = 1.16
3882 reflections
308 parameters
16 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O6ⁱ	0.88 (4)	1.92	2.794 (4)	168
N3—H3A⋯O3	0.80 (3)	2.23	2.990 (6)	159
N4—H4A⋯O5ⁱ	0.71 (4)	2.56	3.233 (5)	160
N4—H4A⋯O7ⁱ	0.71 (4)	2.52	3.133 (5)	145
N6—H6⋯O1	0.84 (3)	2.00	2.838 (8)	178
C1—H1A⋯O7ⁱⁱ	0.98	2.54	3.501 (3)	167
C1—H1B⋯O4ⁱⁱⁱ	0.98	2.33	3.078 (4)	132
C4—H4⋯O8^iv	0.95	2.52	3.392 (7)	152
C10—H10B⋯O4^iv	0.99	2.35	3.082 (5)	130
C13—H13⋯O2ⁱ	0.95	2.41	3.259 (3)	149
C19—H19B⋯O5	0.98	2.57	3.351 (6)	136
C19—H19C⋯O7^v	0.98	2.58	3.207 (7)	122
C19—H19C⋯O8^v	0.98	2.57	3.548 (4)	172
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[-x+{\script{3\over 2}}, -y, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (v) x-1, y, z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XP in SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024616/hg2415sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808024616/hg2415Isup2.hkl

checkCIF report

Comment top

1,8-Naphthyridine and its derivatives are used for binding of mismatched guanine or used as versatile ligands which are able to form metal aggregates with monodentates fashion or chelating bidentate fashion(Nakatani et al., 2000; Nakatani et al., 2001; Ferrarini et al., 1997; Gavrilova & Bosnich, 2004; Baker & Norman, 2004; Stadie et al., 2007). We report here a new 1,8-Naphthyridine compound (Fig. 1).

The title compound reveals 1,8-naphthyridine rings are linked by methenediamine with a dihedral angle between two 1,8-naphthyridine rings of 60.6 (1)°. Each 1,8-naphthyridine ring is an almost planar in which the ten atoms forming the 1,8-naphthyridine ring have mean deviation of 0.03Å from the least-squares plane calculated using the ten atoms. To balance hydrogen ion charge of two 1,8-naphthyridine rings, there are two perchlorate groups in crystal cell. From the packing diagram (Fig. 2), it seems that the intramolecular N–H···O and C–H···O and hydrogen bonds are effective in the stabilization of the crystal structure.

Related literature top

For related literature, see: Baker & Norman (2004); Gavrilova & Bosnich (2004); Nakatani et al. (2000, 2001); Stadie et al. (2007).

For related literature, see: Ferrarini et al. (1997).

Experimental top

To the solution of 2-amino-7-methyl-1,8-naphthyridine (3.18 g, 0.02 mol) in mixed solvent of water (28 mL) and ethanol (2 mL), 37% formadehyde solution (0.86 mL, 0.01 mol) was added dropwise at 0°C and the reaction mixture was stirred at room temperature for 24h. The white precipitate formed was filtered, washed several times with water and then with diethyl ether and dried. Yield: 55% (1.81 g). FTIR (KBr)cm^-1: ν_NH 3389, 3266; ν_CH 3026. Anal. Calc. For C₁₉H₁₈N₆: C, 69.07; H, 5.49; N, 25.44. Found: C, 68.86; H, 5.56; N, 25.37. Single crystals of (I) suitable for an X-ray study were obtained by slow evaporation of an aqueous ethanol solution (30% v/v) under the conditions in the presence of perchloric acid at 293 K over a period of one month.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XP in SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the cation of the title compound showing the atom-numbering scheme and displacement ellipsoids drawn at the 40% probability level.
	Fig. 2. Unit-cell packing diagram as viewed down the c-direction. Hydrogen bonds are shown as dashed lines.

2,2'-Dimethyl-7,7'-(methylenediimino)di-1,8-naphthyridin-1-ium bis(perchlorate) top

Crystal data top

C₁₉H₂₀N₆²⁺·2ClO₄⁻	F(000) = 2192
M_r = 531.31	D_x = 1.599 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7263 reflections
a = 8.1910 (5) Å	θ = 2.1–28.0°
b = 19.3250 (12) Å	µ = 0.36 mm⁻¹
c = 27.8850 (19) Å	T = 113 K
V = 4413.9 (5) Å³	Prism, colorless
Z = 8	0.34 × 0.16 × 0.14 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3882 independent reflections
Radiation source: fine-focus sealed tube	3598 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.0°, θ_min = 2.1°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −22→22
T_min = 0.909, T_max = 0.952	l = −33→32
31220 measured reflections

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ²(F_o²) + (0.0498P)² + 5.3196P] where P = (F_o² + 2F_c²)/3
3882 reflections	(Δ/σ)_max = 0.003
308 parameters	Δρ_max = 0.35 e Å⁻³
16 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₉H₂₀N₆²⁺·2ClO₄⁻	V = 4413.9 (5) Å³
M_r = 531.31	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 8.1910 (5) Å	µ = 0.36 mm⁻¹
b = 19.3250 (12) Å	T = 113 K
c = 27.8850 (19) Å	0.34 × 0.16 × 0.14 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3882 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3598 reflections with I > 2σ(I)
T_min = 0.909, T_max = 0.952	R_int = 0.061
31220 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	16 restraints
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	Δρ_max = 0.35 e Å⁻³
3882 reflections	Δρ_min = −0.41 e Å⁻³
308 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	Occ. (<1)
Cl1	0.24246 (10)	0.22574 (4)	0.56855 (3)	0.0360 (2)
Cl2	1.00163 (9)	0.01682 (3)	0.69459 (3)	0.0323 (2)
O1	0.1693 (6)	0.1730 (2)	0.59780 (16)	0.0534 (14)	0.747 (5)
O2	0.3894 (5)	0.2014 (2)	0.5483 (2)	0.0758 (17)	0.747 (5)
O3	0.1302 (6)	0.2438 (2)	0.53084 (12)	0.0738 (15)	0.747 (5)
O4	0.2651 (6)	0.28664 (19)	0.59698 (15)	0.0700 (14)	0.747 (5)
O5	0.8509 (4)	0.02894 (17)	0.67091 (14)	0.0664 (12)	0.870 (6)
O6	0.9850 (5)	−0.03196 (14)	0.73264 (10)	0.0657 (13)	0.870 (6)
O7	1.1129 (3)	−0.01123 (15)	0.65972 (10)	0.0490 (10)	0.870 (6)
O8	1.0661 (6)	0.0802 (2)	0.7134 (2)	0.0444 (13)	0.870 (6)
O1'	0.1358 (14)	0.1676 (5)	0.5766 (4)	0.039 (3)	0.253 (5)
O2'	0.3710 (11)	0.2233 (6)	0.6037 (3)	0.062 (4)	0.253 (5)
O3'	0.3135 (14)	0.2178 (6)	0.5220 (3)	0.062 (4)	0.253 (5)
O4'	0.1558 (13)	0.2875 (4)	0.5708 (4)	0.052 (3)	0.253 (5)
O5'	0.8301 (12)	0.0031 (10)	0.7058 (7)	0.053 (6)	0.130 (6)
O6'	1.0870 (19)	−0.0453 (6)	0.7069 (7)	0.048 (6)	0.130 (6)
O7'	1.012 (3)	0.0307 (10)	0.6446 (4)	0.062 (7)	0.130 (6)
O8'	1.056 (3)	0.0738 (10)	0.7228 (8)	0.039 (10)	0.130 (6)
N1	0.1466 (3)	0.16498 (13)	0.27420 (9)	0.0328 (6)
N2	0.1460 (3)	0.16453 (12)	0.35633 (8)	0.0293 (6)
N3	0.1396 (3)	0.16601 (15)	0.43819 (10)	0.0353 (6)
N6	0.3295 (3)	0.04505 (14)	0.58097 (9)	0.0336 (6)
N5	0.2041 (3)	0.04253 (13)	0.50731 (9)	0.0327 (6)
N4	0.0922 (4)	0.04231 (16)	0.43264 (11)	0.0417 (7)
C2	0.1739 (4)	0.19127 (16)	0.23034 (10)	0.0377 (8)
C3	0.2463 (5)	0.25570 (18)	0.22665 (11)	0.0435 (9)
H3	0.2634	0.2759	0.1960	0.052*
C4	0.2935 (4)	0.29061 (16)	0.26746 (11)	0.0390 (8)
H4	0.3453	0.3344	0.2647	0.047*
C5	0.2662 (4)	0.26239 (14)	0.31277 (10)	0.0285 (7)
C6	0.1858 (4)	0.19774 (14)	0.31595 (10)	0.0268 (6)
C7	0.1866 (4)	0.19636 (15)	0.39716 (10)	0.0288 (7)
C8	0.2786 (4)	0.25928 (15)	0.39855 (10)	0.0314 (7)
H8	0.3132	0.2779	0.4284	0.038*
C9	0.3159 (4)	0.29193 (15)	0.35722 (10)	0.0324 (7)
H9	0.3748	0.3343	0.3578	0.039*
C1	0.1243 (6)	0.14783 (18)	0.18868 (12)	0.0518 (10)
H1A	0.2123	0.1154	0.1808	0.078*
H1B	0.1026	0.1776	0.1610	0.078*
H1C	0.0253	0.1219	0.1968	0.078*
C16	0.4320 (4)	0.02351 (16)	0.61578 (11)	0.0360 (8)
C17	0.5112 (4)	−0.03943 (17)	0.60916 (12)	0.0402 (8)
H17	0.5862	−0.0556	0.6326	0.048*
C18	0.4812 (4)	−0.07835 (17)	0.56878 (12)	0.0398 (8)
H18	0.5322	−0.1222	0.5653	0.048*
C14	0.3773 (4)	−0.05443 (15)	0.53293 (12)	0.0357 (7)
C15	0.3015 (4)	0.01043 (16)	0.53928 (11)	0.0316 (7)
C11	0.1802 (4)	0.00934 (17)	0.46592 (11)	0.0368 (8)
C12	0.2463 (4)	−0.05808 (16)	0.45608 (12)	0.0424 (8)
H12	0.2221	−0.0808	0.4267	0.051*
C13	0.3428 (4)	−0.08878 (16)	0.48880 (12)	0.0411 (8)
H13	0.3878	−0.1332	0.4825	0.049*
C19	0.4554 (5)	0.06921 (19)	0.65809 (11)	0.0446 (8)
H19A	0.4863	0.1156	0.6473	0.067*
H19B	0.5418	0.0503	0.6785	0.067*
H19C	0.3533	0.0718	0.6763	0.067*
C10	0.0224 (4)	0.10976 (18)	0.43970 (12)	0.0431 (8)
H10A	−0.0336	0.1106	0.4712	0.052*
H10B	−0.0612	0.1178	0.4147	0.052*
H3A	0.163 (4)	0.1865 (17)	0.4619 (12)	0.035 (10)*
H1	0.101 (5)	0.124 (2)	0.2764 (13)	0.055 (11)*
H4A	0.081 (5)	0.0269 (19)	0.4097 (13)	0.040 (12)*
H6	0.281 (4)	0.0828 (18)	0.5853 (12)	0.035 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0433 (5)	0.0317 (4)	0.0331 (4)	−0.0003 (3)	0.0046 (4)	−0.0008 (3)
Cl2	0.0360 (5)	0.0256 (4)	0.0353 (4)	−0.0007 (3)	0.0018 (3)	−0.0012 (3)
O1	0.064 (3)	0.046 (2)	0.050 (3)	0.016 (2)	0.026 (2)	0.022 (2)
O2	0.055 (3)	0.049 (2)	0.124 (4)	−0.002 (2)	0.053 (3)	−0.011 (3)
O3	0.118 (4)	0.059 (2)	0.045 (2)	0.031 (2)	−0.025 (2)	0.0033 (18)
O4	0.089 (3)	0.052 (2)	0.070 (3)	−0.001 (2)	0.002 (3)	−0.027 (2)
O5	0.0421 (19)	0.063 (2)	0.095 (3)	0.0139 (15)	−0.0291 (19)	−0.019 (2)
O6	0.126 (4)	0.0396 (16)	0.0313 (15)	−0.0408 (19)	−0.0042 (19)	0.0050 (12)
O7	0.0410 (17)	0.0542 (18)	0.0519 (18)	−0.0075 (14)	0.0127 (14)	−0.0213 (14)
O8	0.055 (3)	0.0232 (18)	0.055 (2)	−0.0038 (16)	−0.002 (2)	−0.0076 (17)
O1'	0.036 (6)	0.030 (5)	0.051 (7)	−0.003 (4)	0.014 (5)	0.002 (5)
O2'	0.049 (6)	0.086 (7)	0.052 (6)	−0.022 (5)	−0.013 (5)	0.031 (5)
O3'	0.056 (7)	0.087 (7)	0.041 (6)	−0.016 (6)	0.023 (5)	−0.020 (5)
O4'	0.063 (6)	0.027 (4)	0.065 (6)	0.017 (4)	0.012 (5)	0.007 (4)
O5'	0.030 (8)	0.067 (9)	0.061 (10)	0.008 (7)	0.004 (7)	0.003 (8)
O6'	0.046 (9)	0.033 (8)	0.064 (10)	0.009 (7)	0.000 (8)	0.003 (7)
O7'	0.085 (11)	0.060 (10)	0.041 (9)	−0.012 (8)	0.014 (8)	−0.003 (7)
O8'	0.053 (14)	0.032 (13)	0.032 (12)	0.002 (8)	−0.006 (8)	−0.010 (8)
N1	0.0448 (17)	0.0233 (13)	0.0302 (14)	−0.0046 (12)	−0.0070 (12)	0.0000 (10)
N2	0.0321 (14)	0.0275 (12)	0.0283 (13)	−0.0027 (11)	−0.0009 (11)	0.0035 (10)
N3	0.0381 (16)	0.0419 (15)	0.0260 (14)	0.0023 (13)	−0.0004 (12)	0.0032 (12)
N6	0.0353 (15)	0.0344 (15)	0.0310 (14)	0.0059 (13)	0.0054 (12)	0.0103 (12)
N5	0.0314 (14)	0.0360 (14)	0.0306 (13)	−0.0023 (11)	0.0053 (11)	0.0101 (11)
N4	0.0479 (19)	0.0467 (18)	0.0306 (16)	−0.0128 (14)	−0.0024 (15)	0.0084 (14)
C2	0.053 (2)	0.0331 (16)	0.0266 (16)	0.0011 (15)	−0.0066 (15)	−0.0008 (13)
C3	0.064 (2)	0.0381 (18)	0.0287 (16)	−0.0036 (17)	−0.0008 (16)	0.0063 (14)
C4	0.050 (2)	0.0317 (16)	0.0349 (17)	−0.0098 (15)	0.0017 (15)	0.0043 (13)
C5	0.0341 (17)	0.0212 (14)	0.0302 (15)	−0.0031 (12)	−0.0020 (13)	−0.0004 (12)
C6	0.0325 (16)	0.0223 (13)	0.0257 (14)	−0.0012 (12)	−0.0021 (13)	−0.0003 (11)
C7	0.0299 (16)	0.0301 (15)	0.0264 (15)	0.0067 (13)	0.0012 (13)	0.0022 (12)
C8	0.0359 (18)	0.0293 (15)	0.0290 (15)	0.0050 (13)	−0.0035 (13)	−0.0066 (12)
C9	0.0374 (18)	0.0262 (15)	0.0335 (16)	−0.0018 (13)	−0.0029 (14)	−0.0030 (12)
C1	0.083 (3)	0.0408 (19)	0.0316 (18)	−0.0031 (19)	−0.0128 (19)	−0.0052 (15)
C16	0.0290 (17)	0.0429 (18)	0.0362 (17)	−0.0019 (14)	0.0067 (14)	0.0172 (14)
C17	0.0313 (18)	0.0449 (19)	0.0444 (19)	0.0015 (15)	0.0056 (15)	0.0222 (16)
C18	0.0337 (18)	0.0324 (17)	0.053 (2)	0.0026 (14)	0.0174 (16)	0.0202 (15)
C14	0.0355 (18)	0.0285 (15)	0.0430 (18)	−0.0041 (14)	0.0150 (15)	0.0115 (14)
C15	0.0287 (17)	0.0350 (16)	0.0309 (16)	−0.0028 (13)	0.0097 (13)	0.0104 (13)
C11	0.0381 (19)	0.0409 (18)	0.0314 (16)	−0.0138 (15)	0.0053 (15)	0.0099 (14)
C12	0.052 (2)	0.0331 (17)	0.0417 (19)	−0.0172 (16)	0.0116 (17)	0.0006 (15)
C13	0.048 (2)	0.0273 (16)	0.048 (2)	−0.0080 (15)	0.0165 (17)	0.0061 (14)
C19	0.042 (2)	0.058 (2)	0.0341 (17)	−0.0008 (17)	0.0011 (16)	0.0121 (16)
C10	0.0343 (19)	0.061 (2)	0.0343 (18)	−0.0038 (17)	0.0030 (15)	0.0176 (16)

Geometric parameters (Å, º) top

Cl1—O4'	1.390 (7)	C2—C3	1.383 (5)
Cl1—O2	1.410 (4)	C2—C1	1.490 (4)
Cl1—O3'	1.430 (7)	C3—C4	1.378 (4)
Cl1—O4	1.431 (3)	C3—H3	0.9500
Cl1—O1	1.436 (4)	C4—C5	1.394 (4)
Cl1—O2'	1.439 (7)	C4—H4	0.9500
Cl1—O3	1.440 (3)	C5—C6	1.415 (4)
Cl1—O1'	1.441 (8)	C5—C9	1.424 (4)
Cl2—O5	1.420 (3)	C7—C8	1.431 (4)
Cl2—O7'	1.423 (9)	C8—C9	1.349 (4)
Cl2—O8'	1.424 (10)	C8—H8	0.9500
Cl2—O6	1.426 (3)	C9—H9	0.9500
Cl2—O6'	1.432 (9)	C1—H1A	0.9800
Cl2—O8	1.433 (3)	C1—H1B	0.9800
Cl2—O7	1.439 (3)	C1—H1C	0.9800
Cl2—O5'	1.464 (9)	C16—C17	1.390 (5)
N1—C2	1.343 (4)	C16—C19	1.486 (5)
N1—C6	1.364 (4)	C17—C18	1.376 (5)
N1—H1	0.88 (4)	C17—H17	0.9500
N2—C7	1.336 (4)	C18—C14	1.392 (5)
N2—C6	1.336 (4)	C18—H18	0.9500
N3—C7	1.342 (4)	C14—C15	1.410 (4)
N3—C10	1.451 (4)	C14—C13	1.427 (5)
N3—H3A	0.80 (3)	C11—C12	1.437 (5)
N6—C16	1.350 (4)	C12—C13	1.345 (5)
N6—C15	1.360 (4)	C12—H12	0.9500
N6—H6	0.84 (3)	C13—H13	0.9500
N5—C11	1.335 (4)	C19—H19A	0.9800
N5—C15	1.348 (4)	C19—H19B	0.9800
N4—C11	1.337 (4)	C19—H19C	0.9800
N4—C10	1.437 (5)	C10—H10A	0.9900
N4—H4A	0.71 (4)	C10—H10B	0.9900

O4'—Cl1—O2	137.8 (4)	N1—C2—C3	118.7 (3)
O4'—Cl1—O3'	109.9 (6)	N1—C2—C1	116.8 (3)
O4'—Cl1—O4	48.3 (4)	C3—C2—C1	124.5 (3)
O2—Cl1—O4	112.7 (3)	C4—C3—C2	120.0 (3)
O3'—Cl1—O4	122.6 (5)	C4—C3—H3	120.0
O4'—Cl1—O1	111.8 (5)	C2—C3—H3	120.0
O2—Cl1—O1	110.3 (3)	C3—C4—C5	120.8 (3)
O3'—Cl1—O1	127.5 (5)	C3—C4—H4	119.6
O4—Cl1—O1	108.9 (3)	C5—C4—H4	119.6
O4'—Cl1—O2'	111.7 (6)	C4—C5—C6	118.5 (3)
O2—Cl1—O2'	68.8 (5)	C4—C5—C9	125.9 (3)
O3'—Cl1—O2'	108.5 (6)	C6—C5—C9	115.6 (3)
O4—Cl1—O2'	63.6 (5)	N2—C6—N1	116.0 (2)
O1—Cl1—O2'	84.0 (4)	N2—C6—C5	126.2 (3)
O4'—Cl1—O3	59.9 (5)	N1—C6—C5	117.8 (3)
O2—Cl1—O3	109.5 (3)	N2—C7—N3	117.0 (3)
O3'—Cl1—O3	67.9 (5)	N2—C7—C8	123.0 (3)
O4—Cl1—O3	106.7 (2)	N3—C7—C8	120.0 (3)
O1—Cl1—O3	108.7 (3)	C9—C8—C7	119.6 (3)
O2'—Cl1—O3	166.5 (4)	C9—C8—H8	120.2
O4'—Cl1—O1'	110.7 (6)	C7—C8—H8	120.2
O2—Cl1—O1'	108.6 (6)	C8—C9—C5	119.4 (3)
O3'—Cl1—O1'	107.7 (6)	C8—C9—H9	120.3
O4—Cl1—O1'	129.3 (5)	C5—C9—H9	120.3
O2'—Cl1—O1'	108.2 (6)	C2—C1—H1A	109.5
O3—Cl1—O1'	85.2 (5)	C2—C1—H1B	109.5
O5—Cl2—O7'	64.3 (8)	H1A—C1—H1B	109.5
O5—Cl2—O8'	113.6 (11)	C2—C1—H1C	109.5
O7'—Cl2—O8'	112.1 (10)	H1A—C1—H1C	109.5
O5—Cl2—O6	111.8 (2)	H1B—C1—H1C	109.5
O7'—Cl2—O6	149.3 (8)	N6—C16—C17	117.7 (3)
O8'—Cl2—O6	97.5 (11)	N6—C16—C19	117.9 (3)
O5—Cl2—O6'	132.4 (7)	C17—C16—C19	124.4 (3)
O7'—Cl2—O6'	111.3 (8)	C18—C17—C16	120.2 (3)
O8'—Cl2—O6'	111.4 (10)	C18—C17—H17	119.9
O6—Cl2—O6'	46.6 (7)	C16—C17—H17	119.9
O5—Cl2—O8	110.5 (2)	C17—C18—C14	121.0 (3)
O7'—Cl2—O8	100.1 (8)	C17—C18—H18	119.5
O6—Cl2—O8	109.1 (3)	C14—C18—H18	119.5
O6'—Cl2—O8	116.7 (8)	C18—C14—C15	118.3 (3)
O5—Cl2—O7	107.38 (19)	C18—C14—C13	125.9 (3)
O7'—Cl2—O7	50.9 (8)	C15—C14—C13	115.8 (3)
O8'—Cl2—O7	117.9 (11)	N5—C15—N6	116.0 (3)
O6—Cl2—O7	108.3 (2)	N5—C15—C14	125.9 (3)
O6'—Cl2—O7	62.4 (8)	N6—C15—C14	118.1 (3)
O8—Cl2—O7	109.6 (3)	N5—C11—N4	116.8 (3)
O5—Cl2—O5'	45.2 (7)	N5—C11—C12	123.1 (3)
O7'—Cl2—O5'	107.7 (8)	N4—C11—C12	120.2 (3)
O8'—Cl2—O5'	108.7 (10)	C13—C12—C11	119.5 (3)
O6—Cl2—O5'	68.2 (8)	C13—C12—H12	120.3
O6'—Cl2—O5'	105.3 (8)	C11—C12—H12	120.3
O8—Cl2—O5'	115.5 (8)	C12—C13—C14	119.8 (3)
O7—Cl2—O5'	133.2 (8)	C12—C13—H13	120.1
C2—N1—C6	124.2 (3)	C14—C13—H13	120.1
C2—N1—H1	118 (2)	C16—C19—H19A	109.5
C6—N1—H1	117 (2)	C16—C19—H19B	109.5
C7—N2—C6	115.9 (2)	H19A—C19—H19B	109.5
C7—N3—C10	122.8 (3)	C16—C19—H19C	109.5
C7—N3—H3A	115 (2)	H19A—C19—H19C	109.5
C10—N3—H3A	121 (2)	H19B—C19—H19C	109.5
C16—N6—C15	124.6 (3)	N4—C10—N3	114.4 (3)
C16—N6—H6	117 (2)	N4—C10—H10A	108.7
C15—N6—H6	118 (2)	N3—C10—H10A	108.7
C11—N5—C15	116.0 (3)	N4—C10—H10B	108.7
C11—N4—C10	123.5 (3)	N3—C10—H10B	108.7
C11—N4—H4A	120 (3)	H10A—C10—H10B	107.6
C10—N4—H4A	117 (3)

C6—N1—C2—C3	−0.1 (5)	C15—N6—C16—C19	176.9 (3)
C6—N1—C2—C1	179.5 (3)	N6—C16—C17—C18	−1.5 (4)
N1—C2—C3—C4	2.1 (5)	C19—C16—C17—C18	179.8 (3)
C1—C2—C3—C4	−177.4 (4)	C16—C17—C18—C14	2.8 (5)
C2—C3—C4—C5	−1.4 (6)	C17—C18—C14—C15	−0.8 (4)
C3—C4—C5—C6	−1.3 (5)	C17—C18—C14—C13	177.1 (3)
C3—C4—C5—C9	177.0 (3)	C11—N5—C15—N6	178.3 (3)
C7—N2—C6—N1	179.2 (3)	C11—N5—C15—C14	−0.7 (4)
C7—N2—C6—C5	0.2 (4)	C16—N6—C15—N5	−175.3 (3)
C2—N1—C6—N2	178.4 (3)	C16—N6—C15—C14	3.8 (4)
C2—N1—C6—C5	−2.5 (5)	C18—C14—C15—N5	176.7 (3)
C4—C5—C6—N2	−177.9 (3)	C13—C14—C15—N5	−1.5 (4)
C9—C5—C6—N2	3.7 (5)	C18—C14—C15—N6	−2.3 (4)
C4—C5—C6—N1	3.1 (4)	C13—C14—C15—N6	179.5 (3)
C9—C5—C6—N1	−175.3 (3)	C15—N5—C11—N4	−176.0 (3)
C6—N2—C7—N3	176.2 (3)	C15—N5—C11—C12	3.0 (4)
C6—N2—C7—C8	−4.9 (4)	C10—N4—C11—N5	−0.9 (5)
C10—N3—C7—N2	−12.6 (4)	C10—N4—C11—C12	−179.9 (3)
C10—N3—C7—C8	168.5 (3)	N5—C11—C12—C13	−2.9 (5)
N2—C7—C8—C9	5.7 (5)	N4—C11—C12—C13	176.0 (3)
N3—C7—C8—C9	−175.5 (3)	C11—C12—C13—C14	0.5 (5)
C7—C8—C9—C5	−1.4 (5)	C18—C14—C13—C12	−176.5 (3)
C4—C5—C9—C8	178.9 (3)	C15—C14—C13—C12	1.5 (4)
C6—C5—C9—C8	−2.8 (4)	C11—N4—C10—N3	74.2 (4)
C15—N6—C16—C17	−1.9 (4)	C7—N3—C10—N4	85.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6ⁱ	0.88 (4)	1.92	2.794 (4)	168
N3—H3A···O3	0.80 (3)	2.23	2.990 (6)	159
N4—H4A···O5ⁱ	0.71 (4)	2.56	3.233 (5)	160
N4—H4A···O7ⁱ	0.71 (4)	2.52	3.133 (5)	145
N6—H6···O1	0.84 (3)	2.00	2.838 (8)	178
C1—H1A···O7ⁱⁱ	0.98	2.54	3.501 (3)	167
C1—H1B···O4ⁱⁱⁱ	0.98	2.33	3.078 (4)	132
C4—H4···O8^iv	0.95	2.52	3.392 (7)	152
C10—H10B···O4^iv	0.99	2.35	3.082 (5)	130
C13—H13···O2ⁱ	0.95	2.41	3.259 (3)	149
C19—H19B···O5	0.98	2.57	3.351 (6)	136
C19—H19C···O7^v	0.98	2.58	3.207 (7)	122
C19—H19C···O8^v	0.98	2.57	3.548 (4)	172

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+3/2, −y, z−1/2; (iii) x, −y+1/2, z−1/2; (iv) x−1/2, −y+1/2, −z+1; (v) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₀N₆²⁺·2ClO₄⁻
M_r	531.31
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	113
a, b, c (Å)	8.1910 (5), 19.3250 (12), 27.8850 (19)
V (Å³)	4413.9 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.34 × 0.16 × 0.14

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.909, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	31220, 3882, 3598
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.134, 1.16
No. of reflections	3882
No. of parameters	308
No. of restraints	16
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.41

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6ⁱ	0.88 (4)	1.92	2.794 (4)	168
N3—H3A···O3	0.80 (3)	2.23	2.990 (6)	159
N4—H4A···O5ⁱ	0.71 (4)	2.56	3.233 (5)	160
N4—H4A···O7ⁱ	0.71 (4)	2.52	3.133 (5)	145
N6—H6···O1	0.84 (3)	2.00	2.838 (8)	178
C1—H1A···O7ⁱⁱ	0.98	2.54	3.501 (3)	167
C1—H1B···O4ⁱⁱⁱ	0.98	2.33	3.078 (4)	132
C4—H4···O8^iv	0.95	2.52	3.392 (7)	152
C10—H10B···O4^iv	0.99	2.35	3.082 (5)	130
C13—H13···O2ⁱ	0.95	2.41	3.259 (3)	149
C19—H19B···O5	0.98	2.57	3.351 (6)	136
C19—H19C···O7^v	0.98	2.58	3.207 (7)	122
C19—H19C···O8^v	0.98	2.57	3.548 (4)	172

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+3/2, −y, z−1/2; (iii) x, −y+1/2, z−1/2; (iv) x−1/2, −y+1/2, −z+1; (v) x−1, y, z.

Acknowledgements

We thank Henan Agricultural University for the generous support of this study.

References

Baker, R. S. & Norman, R. E. (2004). Acta Cryst. E60, m1761–m1763. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ferrarini, P. L., Mori, C., Badawneh, M., Manera, C., Martinelli, A., Miceli, M., Ramagnoli, F. & Saccomanni, G. (1997). J. Heterocycl. Chem. 34, 1501–1504. CrossRef CAS Google Scholar
Gavrilova, E. L. & Bosnich, B. (2004). Chem. Rev. 104, 349–383. Web of Science CrossRef PubMed CAS Google Scholar
Nakatani, K., Sando, S. & Saito, I. (2000). J. Am. Chem. Soc. 122, 2172–2178. Web of Science CrossRef CAS Google Scholar
Nakatani, K., Sando, S. & Saito, I. (2001). Nat. Biotechnol. 19, 51–55. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stadie, N. P., Sanchez-Smith, R. & Groy, T. L. (2007). Acta Cryst. E63, m2153–m2154. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 64| Part 9| September 2008| Page o1702

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

Retracted: 2,2′-Di­methyl-7,7′-(methyl­enedi­imino)di-1,8-naphthyridin-1-ium bis­­(perchlorate)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Retracted: 2,2′-Dimethyl-7,7′-(methylenediimino)di-1,8-naphthyridin-1-ium bis(perchlorate)