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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 6| June 2010| Page o1359
https://doi.org/10.1107/S1600536810017113

4,4′-Di­methyl-1,1′-(p-phenyl­enedi­methyl­ene)dipyridinium bis­­[7,7,8,8-tetra­cyano­quinodimethanide(1−)]

Guang-Xiang Liua*

aAnhui Key Laboratory of Functional Coordination Compounds, School of Chemistry and Chemical Engineering, Anqing Normal University, Anqing 246003, People's Republic of China
*Correspondence e-mail: liugx@live.com

(Received 3 May 2010; accepted 10 May 2010; online 15 May 2010)

In the title salt, C20H22N22+·2C12H4N4−, the cations and anions stack along the b axis into segregated columns. In the cation, which has a crystallographically imposed centre of symmetry, the dihedral angle between the benzene and pyridine rings is 89.14 (4)°. Centrosymmetrically related anions form dimers by π–π stacking inter­actions, with centroid–centroid separations of 3.874 (4) Å. The crystal packing is stabilized by inter­columnar C—H⋯N hydrogen bonds.

Related literature

For general background to the planar organic mol­ecule 7,7,8,8-tetra­cyano­quinodimethane, see: Alonso et al. (2005[Alonso, C., Ballester, L., Gutiérrez, A., Perpiñán, M. F., Sánchez, A. E. & Azcondo, M. T. (2005). Eur. J. Inorg. Chem. pp. 486-495.]); Madalan et al. (2002[Madalan, A. M., Roesky, H. W., Andruh, M., Noltemeyerb, M. & Stanicac, N. (2002). Chem. Commun. pp. 1638-1639.]); Liu et al. (2008[Liu, G. X., Xu, H., Ren, X. M. & Sun, W. Y. (2008). CrystEngComm, 10, 1574-1582.]). For the role played by the size and shape of the counter-cations in determining the ground-state electronic properties of the resulting materials, see: Ren, Meng et al. (2002[Ren, X. M., Meng, Q. J., Song, Y., Lu, C. S., Hu, C. J. & Chen, X. Y. (2002). Inorg. Chem. 41, 5686-5692.]); Ren, et al. (2003[Ren, X. M., Ma, J., Lu, C. S., Yang, S. Z., Meng, Q. J. & Wu, P. H. (2003). Dalton Trans. pp. 1345-1351.]); Ren, Chen et al. (2002[Ren, X. M., Chen, Y. C., He, C. & Gao, S. (2002). J. Chem. Soc. Dalton Trans. pp. 3915-3918.]). For related structures, see: Liu et al. (2005[Liu, G. X., Ren, X. M., Kremer, P. K. & Meng, Q. J. (2005). J. Mol. Struct. 743, 125-133.]).

[Scheme 1]

Experimental

Crystal data

  • C20H22N22+·2C12H4N4−

  • Mr = 698.78

  • Triclinic, [P \overline 1]

  • a = 8.5904 (12) Å

  • b = 8.6786 (11) Å

  • c = 13.3016 (17) Å

  • α = 101.558 (2)°

  • β = 106.134 (2)°

  • γ = 97.906 (2)°

  • V = 913.4 (2) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.24 × 0.22 × 0.16 mm
Data collection

  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.981, Tmax = 0.988

  • 6854 measured reflections

  • 3353 independent reflections

  • 2243 reflections with I > 2σ(I)

  • Rint = 0.023
Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.126

  • S = 1.00

  • 3353 reflections

  • 245 parameters

  • H-atom parameters constrained

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C16—H16⋯N3i 0.93 2.62 3.320 (3) 132
C17—H17⋯N2ii 0.93 2.47 3.204 (3) 136
C19—H19A⋯N3i 0.97 2.57 3.394 (3) 143
Symmetry codes: (i) x+1, y-1, z; (ii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810017113/rz2446sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810017113/rz2446Isup2.hkl

checkCIF report


Comment top

The search for new compounds with promising electronic, and magnetic properties has prompted chemists to combine different spin carriers within the same molecular or supramolecular entity (Madalan et al., 2002). One of the most extensively used radicals in these studies has been the planar organic molecule 7,7,8,8-tetracyanoquinodimethane, [C8H4(CN)4], TCNQ, since it shows a low reduction potential which makes it a suitable acceptor in charge-transfer processes. Another significant feature of this acceptor is its tendency to overlap its π-delocalized system with those of neighbouring molecules to form stacks with different degrees of electron delocalization (Alonso et al., 2005). Previous work has shown that molecular stacks of charge-transfer salts exhibit low-dimensional properties in some cases, which have intriguing anisotropic magnetic, electronic and structural characteristics (Ren, Meng et al., 2002; Ren et al., 2003; Liu et al., 2005). Furthermore, the size and shape of the counter-cations play an important role in determining the ground-state properties of the resulting materials (Ren, Chen et al., 2002; Liu et al., 2008). As a result, charge-transfer salts consisting of the TCNQ anion and benzylpyridinium cations could offer the possibility of systematically studying the fundamental relationship between the stack structure and the size and steric properties of substituent groups. In this communication, the crystal structure of the title complex is reported.

The asymmetric unit of the title compound contains a half of a (C20H22N2)2+ cation and one [C8H4(CN)4]- anion (Fig. 1). Anions and cations stack into completely segregated columns along the b axis, as illustrated in Fig. 2. Within an anion column, [(TCNQ)2]2- dimers are formed by π···π stacking interactions with a centroid-to-centroid distance of 3.874 (4) Å, and adjacent units are displaced relative to each other along the direction of the shorter molecular axis of TCNQ with centroid-to-centroid separations of 6.556 (4) Å (Fig. 3). The (C20H22N2)2+ cation affords a trans conformation, with a dihedral angle between the benzene ring and the pyridine rings of 89.14 (4)°. The crystal packing is stabilized by C—H···N intercolumar linkages (Table 1).

Related literature top

For general background to the planar organic molecule 7,7,8,8-tetracyanoquinodimethane, see: Alonso et al. (2005); Madalan et al. (2002); Liu et al. (2008). For the role played by the size and shape of the counter-cations in determining the ground-state properties of the resulting materials, see: Ren, Meng et al. (2002); Ren, et al. (2003); Ren, Chen et al. (2002). For related structures, see: Liu et al. (2005).

Experimental top

1,1'-(1,4-Phenylenebis(methylene))bis(4-methylpyridin-1-ium) iodide was prepared by the direct combination of 1:2 molar equivalents of 1,1'-(1,4-phenylenebis(methylene))bis(4-methylpyridin-1-ium) chloride and NaI in a warm acetone solution at 313 K. A white precipitate was formed (NaCl), which was filtered off, and a white microcrystalline product was obtained by evaporating the filtrate. 1:2 Molar equivalents of 1,1'-(1,4-phenylenebis(methylene))bis(4-methylpyridin-1-ium) iodide and LiTCNQ were mixed directly in a methanol solution, and the mixture was refluxed for 12 h. The black microcrystalline product which formed was filtered off, washed with MeOH and dried in vacuo. Single crystals of the title compound suitable for X-ray structure analysis were obtained by diffusing diethyl ether into a MeCN solution.

Refinement top

H atoms were positioned geometrically, with C—H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Structure description top

The search for new compounds with promising electronic, and magnetic properties has prompted chemists to combine different spin carriers within the same molecular or supramolecular entity (Madalan et al., 2002). One of the most extensively used radicals in these studies has been the planar organic molecule 7,7,8,8-tetracyanoquinodimethane, [C8H4(CN)4], TCNQ, since it shows a low reduction potential which makes it a suitable acceptor in charge-transfer processes. Another significant feature of this acceptor is its tendency to overlap its π-delocalized system with those of neighbouring molecules to form stacks with different degrees of electron delocalization (Alonso et al., 2005). Previous work has shown that molecular stacks of charge-transfer salts exhibit low-dimensional properties in some cases, which have intriguing anisotropic magnetic, electronic and structural characteristics (Ren, Meng et al., 2002; Ren et al., 2003; Liu et al., 2005). Furthermore, the size and shape of the counter-cations play an important role in determining the ground-state properties of the resulting materials (Ren, Chen et al., 2002; Liu et al., 2008). As a result, charge-transfer salts consisting of the TCNQ anion and benzylpyridinium cations could offer the possibility of systematically studying the fundamental relationship between the stack structure and the size and steric properties of substituent groups. In this communication, the crystal structure of the title complex is reported.

The asymmetric unit of the title compound contains a half of a (C20H22N2)2+ cation and one [C8H4(CN)4]- anion (Fig. 1). Anions and cations stack into completely segregated columns along the b axis, as illustrated in Fig. 2. Within an anion column, [(TCNQ)2]2- dimers are formed by π···π stacking interactions with a centroid-to-centroid distance of 3.874 (4) Å, and adjacent units are displaced relative to each other along the direction of the shorter molecular axis of TCNQ with centroid-to-centroid separations of 6.556 (4) Å (Fig. 3). The (C20H22N2)2+ cation affords a trans conformation, with a dihedral angle between the benzene ring and the pyridine rings of 89.14 (4)°. The crystal packing is stabilized by C—H···N intercolumar linkages (Table 1).

For general background to the planar organic molecule 7,7,8,8-tetracyanoquinodimethane, see: Alonso et al. (2005); Madalan et al. (2002); Liu et al. (2008). For the role played by the size and shape of the counter-cations in determining the ground-state properties of the resulting materials, see: Ren, Meng et al. (2002); Ren, et al. (2003); Ren, Chen et al. (2002). For related structures, see: Liu et al. (2005).

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
[Figure 1] Fig. 1. The asymmetric unit of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms are omitted for clarity.
[Figure 2] Fig. 2. Packing diagram of the title compound viewed along the b axis. Hydrogen bonds are shown as dashed lines.
[Figure 3] Fig. 3. A side view of the one-dimensional anion column of the title compound. Hydrogen atoms are omitted for clarity.
4,4'-Dimethyl-1,1'-(p-phenylenedimethylene)dipyridinium bis[7,7,8,8-tetracyanoquinodimethanide(1-)] top
Crystal data top
C20H22N22+·2C12H4N4−Z = 1
Mr = 698.78F(000) = 364
Triclinic, P1Dx = 1.270 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.5904 (12) ÅCell parameters from 2212 reflections
b = 8.6786 (11) Åθ = 2.5–26.4°
c = 13.3016 (17) ŵ = 0.08 mm−1
α = 101.558 (2)°T = 293 K
β = 106.134 (2)°Block, dark green
γ = 97.906 (2)°0.24 × 0.22 × 0.16 mm
V = 913.4 (2) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		3353 independent reflections
Radiation source: sealed tube2243 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
phi and ω scansθmax = 25.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −10→10
Tmin = 0.981, Tmax = 0.988k = −10→10
6854 measured reflectionsl = −16→15
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0561P)2 + 0.1398P]
where P = (Fo2 + 2Fc2)/3
3353 reflections(Δ/σ)max = 0.036
245 parametersΔρmax = 0.15 e Å−3
0 restraintsΔρmin = −0.18 e Å−3
Crystal data top
C20H22N22+·2C12H4N4−γ = 97.906 (2)°
Mr = 698.78V = 913.4 (2) Å3
Triclinic, P1Z = 1
a = 8.5904 (12) ÅMo Kα radiation
b = 8.6786 (11) ŵ = 0.08 mm−1
c = 13.3016 (17) ÅT = 293 K
α = 101.558 (2)°0.24 × 0.22 × 0.16 mm
β = 106.134 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		3353 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		2243 reflections with I > 2σ(I)
Tmin = 0.981, Tmax = 0.988Rint = 0.023
6854 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.126H-atom parameters constrained
S = 1.00Δρmax = 0.15 e Å−3
3353 reflectionsΔρmin = −0.18 e Å−3
245 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
xyzUiso*/Ueq
C10.3619 (2)0.1249 (2)−0.12031 (15)0.0513 (5)
C20.1730 (3)0.2868 (2)−0.18890 (17)0.0594 (5)
C30.2953 (2)0.2639 (2)−0.09960 (15)0.0505 (5)
C40.3415 (2)0.3713 (2)0.00302 (15)0.0464 (4)
C50.4625 (2)0.3502 (2)0.09308 (15)0.0482 (5)
H50.51250.26200.08490.058*
C60.5072 (2)0.4564 (2)0.19137 (15)0.0502 (5)
H60.58730.43880.24890.060*
C70.4357 (2)0.5930 (2)0.20912 (15)0.0488 (4)
C80.3129 (2)0.6118 (2)0.11922 (16)0.0553 (5)
H80.26180.69910.12770.066*
C90.2674 (2)0.5063 (2)0.02115 (16)0.0550 (5)
H90.18540.5228−0.03580.066*
C100.4820 (2)0.7038 (2)0.31119 (16)0.0547 (5)
C110.5983 (3)0.6827 (3)0.40268 (19)0.0699 (6)
C120.4142 (2)0.8429 (3)0.32460 (16)0.0595 (5)
C130.7386 (3)0.2441 (4)0.4765 (2)0.1005 (9)
H13A0.72870.35320.50070.151*
H13B0.78320.20310.53800.151*
H13C0.63140.17960.43440.151*
C140.8517 (2)0.2386 (3)0.40876 (15)0.0615 (6)
C150.9129 (2)0.1013 (3)0.38115 (16)0.0603 (5)
H150.88380.01160.40540.072*
C161.0148 (2)0.0970 (2)0.31919 (15)0.0516 (5)
H161.05580.00490.30190.062*
C171.0016 (2)0.3596 (2)0.30954 (15)0.0541 (5)
H171.03310.44840.28510.065*
C180.9013 (2)0.3681 (3)0.37146 (16)0.0608 (5)
H180.86490.46290.38940.073*
C191.1638 (2)0.2155 (2)0.21295 (15)0.0556 (5)
H19A1.26190.17900.24780.067*
H19B1.19900.32180.20430.067*
C201.0766 (2)0.1027 (2)0.10308 (15)0.0463 (4)
C211.1573 (2)−0.0062 (2)0.05873 (16)0.0536 (5)
H211.2635−0.01180.09800.064*
C220.9181 (2)0.1069 (2)0.04324 (15)0.0537 (5)
H220.86140.17880.07220.064*
N10.4125 (2)0.0106 (2)−0.13825 (15)0.0691 (5)
N20.0727 (3)0.3070 (2)−0.25956 (17)0.0860 (7)
N30.3576 (3)0.9543 (2)0.33418 (17)0.0811 (6)
N40.6931 (3)0.6641 (3)0.47670 (18)0.1053 (8)
N51.05663 (17)0.22537 (17)0.28280 (11)0.0450 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0510 (10)0.0456 (11)0.0541 (12)0.0084 (9)0.0109 (9)0.0147 (9)
C20.0663 (13)0.0334 (10)0.0669 (14)0.0076 (9)0.0044 (11)0.0116 (10)
C30.0517 (10)0.0386 (10)0.0582 (12)0.0100 (8)0.0089 (9)0.0170 (9)
C40.0477 (10)0.0360 (9)0.0550 (11)0.0079 (8)0.0131 (9)0.0154 (9)
C50.0449 (10)0.0412 (10)0.0595 (12)0.0126 (8)0.0129 (9)0.0171 (9)
C60.0451 (10)0.0483 (11)0.0552 (12)0.0115 (8)0.0091 (9)0.0170 (9)
C70.0455 (10)0.0453 (10)0.0563 (12)0.0085 (8)0.0160 (9)0.0149 (9)
C80.0569 (11)0.0444 (11)0.0645 (13)0.0195 (9)0.0148 (10)0.0133 (10)
C90.0552 (11)0.0450 (11)0.0607 (13)0.0171 (9)0.0060 (10)0.0170 (10)
C100.0542 (11)0.0528 (12)0.0578 (12)0.0164 (9)0.0174 (10)0.0119 (10)
C110.0687 (14)0.0693 (15)0.0610 (15)0.0259 (11)0.0103 (12)−0.0010 (11)
C120.0608 (12)0.0614 (14)0.0584 (13)0.0173 (11)0.0207 (10)0.0136 (11)
C130.0858 (17)0.130 (2)0.0825 (18)0.0091 (16)0.0458 (15)0.0010 (16)
C140.0526 (11)0.0783 (15)0.0427 (11)0.0085 (10)0.0121 (9)−0.0015 (10)
C150.0645 (12)0.0624 (13)0.0504 (12)0.0020 (10)0.0153 (10)0.0179 (10)
C160.0573 (11)0.0398 (10)0.0558 (12)0.0097 (8)0.0135 (9)0.0137 (9)
C170.0651 (12)0.0447 (11)0.0493 (11)0.0178 (9)0.0093 (10)0.0130 (9)
C180.0618 (12)0.0584 (13)0.0556 (13)0.0218 (10)0.0106 (10)0.0042 (10)
C190.0538 (11)0.0557 (12)0.0555 (12)0.0047 (9)0.0199 (10)0.0105 (10)
C200.0470 (10)0.0473 (10)0.0496 (11)0.0104 (8)0.0197 (9)0.0165 (8)
C210.0462 (10)0.0610 (12)0.0566 (12)0.0184 (9)0.0149 (9)0.0180 (10)
C220.0551 (11)0.0543 (12)0.0576 (12)0.0216 (9)0.0234 (10)0.0120 (10)
N10.0723 (11)0.0566 (11)0.0773 (13)0.0242 (9)0.0182 (10)0.0145 (9)
N20.0910 (14)0.0543 (11)0.0851 (14)0.0136 (10)−0.0172 (12)0.0205 (10)
N30.0905 (14)0.0739 (13)0.0845 (14)0.0362 (11)0.0307 (12)0.0143 (11)
N40.1095 (17)0.1122 (18)0.0688 (14)0.0548 (15)−0.0072 (13)−0.0060 (13)
N50.0505 (8)0.0400 (8)0.0415 (8)0.0092 (7)0.0110 (7)0.0083 (7)
Geometric parameters (Å, º) top
C1—N11.145 (2)C13—H13B0.9600
C1—C31.415 (3)C13—H13C0.9600
C2—N21.146 (2)C14—C181.379 (3)
C2—C31.419 (3)C14—C151.391 (3)
C3—C41.406 (3)C15—C161.358 (3)
C4—C51.413 (2)C15—H150.9300
C4—C91.419 (2)C16—N51.344 (2)
C5—C61.359 (2)C16—H160.9300
C5—H50.9300C17—N51.337 (2)
C6—C71.416 (2)C17—C181.347 (3)
C6—H60.9300C17—H170.9300
C7—C81.412 (3)C18—H180.9300
C7—C101.413 (3)C19—N51.477 (2)
C8—C91.353 (3)C19—C201.507 (3)
C8—H80.9300C19—H19A0.9700
C9—H90.9300C19—H19B0.9700
C10—C111.406 (3)C20—C221.383 (2)
C10—C121.412 (3)C20—C211.380 (2)
C11—N41.146 (3)C21—C22i1.380 (3)
C12—N31.141 (2)C21—H210.9300
C13—C141.497 (3)C22—C21i1.380 (3)
C13—H13A0.9600C22—H220.9300
N1—C1—C3178.6 (2)C18—C14—C15116.78 (18)
N2—C2—C3178.5 (2)C18—C14—C13122.2 (2)
C4—C3—C2121.18 (16)C15—C14—C13121.1 (2)
C4—C3—C1123.07 (16)C16—C15—C14120.68 (19)
C2—C3—C1115.72 (17)C16—C15—H15119.7
C3—C4—C5122.03 (16)C14—C15—H15119.7
C3—C4—C9121.27 (16)N5—C16—C15120.27 (18)
C5—C4—C9116.70 (17)N5—C16—H16119.9
C6—C5—C4121.22 (16)C15—C16—H16119.9
C6—C5—H5119.4N5—C17—C18120.89 (19)
C4—C5—H5119.4N5—C17—H17119.6
C5—C6—C7122.16 (17)C18—C17—H17119.6
C5—C6—H6118.9C17—C18—C14121.10 (19)
C7—C6—H6118.9C17—C18—H18119.4
C8—C7—C10121.36 (17)C14—C18—H18119.4
C8—C7—C6116.30 (17)N5—C19—C20112.18 (14)
C10—C7—C6122.33 (17)N5—C19—H19A109.2
C9—C8—C7121.90 (17)C20—C19—H19A109.2
C9—C8—H8119.1N5—C19—H19B109.2
C7—C8—H8119.1C20—C19—H19B109.2
C8—C9—C4121.70 (17)H19A—C19—H19B107.9
C8—C9—H9119.1C22—C20—C21118.33 (17)
C4—C9—H9119.1C22—C20—C19121.95 (17)
C11—C10—C12117.16 (18)C21—C20—C19119.70 (16)
C11—C10—C7122.08 (17)C20—C21—C22i120.67 (17)
C12—C10—C7120.74 (18)C20—C21—H21119.7
N4—C11—C10179.3 (2)C22i—C21—H21119.7
N3—C12—C10179.1 (2)C20—C22—C21i121.00 (17)
C14—C13—H13A109.5C20—C22—H22119.5
C14—C13—H13B109.5C21i—C22—H22119.5
H13A—C13—H13B109.5C17—N5—C16120.25 (16)
C14—C13—H13C109.5C17—N5—C19120.70 (15)
H13A—C13—H13C109.5C16—N5—C19119.05 (15)
H13B—C13—H13C109.5
C2—C3—C4—C5179.72 (17)C18—C14—C15—C16−0.8 (3)
C1—C3—C4—C51.8 (3)C13—C14—C15—C16179.7 (2)
C2—C3—C4—C90.1 (3)C14—C15—C16—N5−0.6 (3)
C1—C3—C4—C9−177.77 (18)N5—C17—C18—C14−0.3 (3)
C3—C4—C5—C6179.13 (17)C15—C14—C18—C171.3 (3)
C9—C4—C5—C6−1.2 (2)C13—C14—C18—C17−179.2 (2)
C4—C5—C6—C70.0 (3)N5—C19—C20—C2246.7 (2)
C5—C6—C7—C81.0 (3)N5—C19—C20—C21−134.85 (17)
C5—C6—C7—C10−179.94 (18)C22—C20—C21—C22i0.7 (3)
C10—C7—C8—C9−179.89 (19)C19—C20—C21—C22i−177.80 (17)
C6—C7—C8—C9−0.8 (3)C21—C20—C22—C21i−0.7 (3)
C7—C8—C9—C4−0.4 (3)C19—C20—C22—C21i177.76 (17)
C3—C4—C9—C8−178.94 (18)C18—C17—N5—C16−1.2 (3)
C5—C4—C9—C81.4 (3)C18—C17—N5—C19178.69 (17)
C8—C7—C10—C11176.93 (19)C15—C16—N5—C171.7 (3)
C6—C7—C10—C11−2.1 (3)C15—C16—N5—C19−178.25 (16)
C8—C7—C10—C12−4.2 (3)C20—C19—N5—C17−110.79 (18)
C6—C7—C10—C12176.78 (18)C20—C19—N5—C1669.1 (2)
Symmetry code: (i) −x+2, −y, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···N3ii0.932.623.320 (3)132
C17—H17···N2iii0.932.473.204 (3)136
C19—H19A···N3ii0.972.573.394 (3)143
Symmetry codes: (ii) x+1, y−1, z; (iii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formulaC20H22N22+·2C12H4N4−
Mr698.78
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.5904 (12), 8.6786 (11), 13.3016 (17)
α, β, γ (°)101.558 (2), 106.134 (2), 97.906 (2)
V (Å3)913.4 (2)
Z1
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.24 × 0.22 × 0.16
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.981, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections		6854, 3353, 2243
Rint0.023
(sin θ/λ)max (Å−1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.126, 1.00
No. of reflections3353
No. of parameters245
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.15, −0.18

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···AD—HH···AD···AD—H···A
C16—H16···N3i0.932.623.320 (3)132
C17—H17···N2ii0.932.473.204 (3)136
C19—H19A···N3i0.972.573.394 (3)143
Symmetry codes: (i) x+1, y−1, z; (ii) −x+1, −y+1, −z.
 

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 20971004), the Key Project of the Chinese Ministry of Education (No. 210102) and the Natural Science Foundation of Educational Commission of Anhui Province of China (No. KJ2010A229).

References

First citationAlonso, C., Ballester, L., Gutiérrez, A., Perpiñán, M. F., Sánchez, A. E. & Azcondo, M. T. (2005). Eur. J. Inorg. Chem. pp. 486–495.  Web of Science CSD CrossRef Google Scholar
 First citationBruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationLiu, G. X., Ren, X. M., Kremer, P. K. & Meng, Q. J. (2005). J. Mol. Struct. 743, 125–133.  Web of Science CSD CrossRef CAS Google Scholar
 First citationLiu, G. X., Xu, H., Ren, X. M. & Sun, W. Y. (2008). CrystEngComm, 10, 1574–1582.  Web of Science CSD CrossRef CAS Google Scholar
 First citationMadalan, A. M., Roesky, H. W., Andruh, M., Noltemeyerb, M. & Stanicac, N. (2002). Chem. Commun. pp. 1638–1639.  Web of Science CSD CrossRef Google Scholar
 First citationRen, X. M., Chen, Y. C., He, C. & Gao, S. (2002). J. Chem. Soc. Dalton Trans. pp. 3915–3918.  Web of Science CSD CrossRef Google Scholar
 First citationRen, X. M., Ma, J., Lu, C. S., Yang, S. Z., Meng, Q. J. & Wu, P. H. (2003). Dalton Trans. pp. 1345–1351.  Web of Science CSD CrossRef Google Scholar
 First citationRen, X. M., Meng, Q. J., Song, Y., Lu, C. S., Hu, C. J. & Chen, X. Y. (2002). Inorg. Chem. 41, 5686–5692.  Web of Science CSD CrossRef PubMed CAS 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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ISSN: 2056-9890
Volume 66| Part 6| June 2010| Page o1359
https://doi.org/10.1107/S1600536810017113
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