A charge-transfer salt, 3,5-dimethyl-1-(4-nitro­benz­yl)pyridinium 7,7,8,8-tetra­cyano­quinodimethane

Wang, M.; Zhou, H.-B.; Chen, Y.-C.

doi:10.1107/S1600536808008258

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o798

doi:10.1107/S1600536808008258

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A charge-transfer salt, 3,5-dimethyl-1-(4-nitrobenzyl)pyridinium 7,7,8,8-tetracyanoquinodimethane

Min Wang,^a Hong-Bo Zhou ^a and You-Cun Chen ^a ^*

^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 16 March 2008; accepted 26 March 2008; online 4 April 2008)

In the title salt, C₁₄H₁₅N₂O₂⁺·C₁₂H₄N₄⁻, the asymmetric unit contains one cation and one anion. C—H⋯N and C—H⋯N and C—H⋯O hydrogen bonds and π–π stacking interactions (interplanar distance 3.845 Å) are found in the crystal structure.

Related literature

For general background, see: Madalan et al. (2002 ); Ren, Chen et al. (2002 ); Ren et al. (2003 ); Ren, Meng et al. (2002 ). For related literature, see: Liu et al. (2005 ); Wang et al. (2006 ).

Experimental

Crystal data

C₁₄H₁₅N₂O₂⁺·C₁₂H₄N₄⁻
M_r = 447.47
Triclinic, $[P \overline 1]$
a = 8.098 (2) Å
b = 9.137 (2) Å
c = 16.542 (4) Å
α = 76.194 (3)°
β = 75.951 (3)°
γ = 86.933 (3)°
V = 1153.0 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.18 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.985, T_max = 0.992
5765 measured reflections
3998 independent reflections
3255 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.144
S = 1.00
3998 reflections
309 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯N2	0.93	2.56	2.895 (2)	102
C7—H7B⋯N4ⁱ	0.97	2.43	3.245 (3)	141
C8—H8⋯O2ⁱⁱ	0.93	2.46	3.119 (2)	128
Symmetry codes: (i) x-1, y-1, z; (ii) x, y+1, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus; 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/S1600536808008258/cf2189sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008258/cf2189Isup2.hkl

checkCIF report

Comment top

Recently, using benzylpyridinium derivatives ([RBzPy]⁺ where R represents a substituent group) with flexible molecular configuration as a counter-cation to control the arrangement of anions [M(mnt)₂]^- (M = Ni, Pd, Pt), a series of ion-pair compounds that show segregated columnar stacks of cations and anions has been prepared (Madalan et al., 2002; Ren, Chen et al., 2002; Ren et al., 2003; Ren, Meng et al., 2002). The radical of TCNQ also shows a planar arrangement and extended electronic structures that are similar to the [M(mnt)₂]^- ion, and has been extensively used to build molecular solids with low-dimensional conductivity and magnetic features, in which the electronic transport and magnetically coupled interactions can be achieved through π–π interactions between radicals along the direction of the radical stack column (Liu et al., 2005; Wang et al., 2006). This character of the TCNQ^- ion prompted us to extend our research to a series of [RBzPy][TCNQ] compounds in order to gain more insight into the relationship between the intermolecular cooperation interactions and the magnetic properties of the compounds with low-dimensional structural features. In this paper, we report the crystal structure of the title compound.

The asymmetric unit contains one (C₁₄H₁₅N₂O₂)⁺ cation and one [C₈H₄(CN)₄]^- anion (Fig. 1). It stacks as completely segregated columns of TCNQ anions/molecules and 3,5-dimethyl-1-(4-nitrobenzyl)pyridinium cations, as illustrated by the projection along the crystallographic a axis in Fig. 2. The cation and anion columns are linked by hydrogen-bonding interactions. Within an anionic column, a strongly bound [(TCNQ)₂]^2- unit is formed, and adjacent units are displaced relative to each other along the direction of the shorter molecular axis of TCNQ. The benzene rings are parallel to each other. In a TCNQ column, the mean interplanar separations within two different overlapping pairs are 5.745 Å inter-dimer and 3.845 Å intra-dimer, respectively, indicating weak π–π stacking interactions. The (C₁₄H₁₅N₂O₂)⁺ cation has a Λ-shaped conformation, and the dihedral angles formed by the C4/C7/N2 plane with the benzene and pyridinium rings are 4.12 (11) and 80.45 (12)°, respectively.

Related literature top

For general background, see: Madalan et al. (2002); Ren, Chen et al. (2002); Ren et al. (2003); Ren, Meng et al. (2002). For related literature, see: Liu et al. (2005); Wang et al. (2006).

Experimental top

3,5-Dimethyl-1-(4-nitrobenzyl)pyridinium iodide was prepared by the direct combination of 1:1 molar equivalents of 3,5-dimethyl-1-(4-nitrobenzyl)pyridinium chloride and NaI in a warm solution in acetone 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 3,5-dimethyl-1-(4-nitrobenzyl)pyridinium iodide and TCNQ were mixed directly in a solution in methanol, and the mixture was refluxed for 12 h. The dark-green microcrystalline product which formed was filtered off, washed with MeOH and dried in vacuo. Single crystals of (I) suitable for structure analysis were obtained by diffusing diethyl ether into an acetonitrile solution of (I).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus (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. The asymmetric unit, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram for (I). Hydrogen bonds are shown as dashed lines.
	Fig. 3. A side-view of the one-dimensional anionic stack of (I).

3,5-dimethyl-1-(4-nitrobenzyl)pyridinium 7,7,8,8-tetracyanoquinodimethane top

Crystal data top

C₁₄H₁₅N₂O₂⁺·C₁₂H₄N₄⁻	Z = 2
M_r = 447.47	F(000) = 466
Triclinic, P1	D_x = 1.289 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.098 (2) Å	Cell parameters from 3033 reflections
b = 9.137 (2) Å	θ = 2.3–27.9°
c = 16.542 (4) Å	µ = 0.09 mm⁻¹
α = 76.194 (3)°	T = 293 K
β = 75.951 (3)°	Pillar, purple
γ = 86.933 (3)°	0.18 × 0.12 × 0.10 mm
V = 1153.0 (5) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	3998 independent reflections
Radiation source: sealed tube	3255 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
T_min = 0.985, T_max = 0.992	k = −10→10
5765 measured reflections	l = −19→16

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0904P)² + 0.1284P] where P = (F_o² + 2F_c²)/3
3998 reflections	(Δ/σ)_max < 0.001
309 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₄H₁₅N₂O₂⁺·C₁₂H₄N₄⁻	γ = 86.933 (3)°
M_r = 447.47	V = 1153.0 (5) Å³
Triclinic, P1	Z = 2
a = 8.098 (2) Å	Mo Kα radiation
b = 9.137 (2) Å	µ = 0.09 mm⁻¹
c = 16.542 (4) Å	T = 293 K
α = 76.194 (3)°	0.18 × 0.12 × 0.10 mm
β = 75.951 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	3998 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3255 reflections with I > 2σ(I)
T_min = 0.985, T_max = 0.992	R_int = 0.018
5765 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.144	H-atom parameters constrained
S = 1.00	Δρ_max = 0.15 e Å⁻³
3998 reflections	Δρ_min = −0.20 e Å⁻³
309 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	0.3034 (2)	−0.11674 (18)	0.07248 (10)	0.0532 (4)
C2	0.1837 (3)	−0.0094 (3)	0.06055 (17)	0.0920 (8)
H2	0.0998	−0.0228	0.0332	0.110*
C3	0.1875 (3)	0.1190 (3)	0.08930 (16)	0.0863 (7)
H3	0.1066	0.1934	0.0805	0.104*
C4	0.30938 (19)	0.13943 (17)	0.13103 (9)	0.0464 (4)
C5	0.4274 (2)	0.02782 (18)	0.14337 (11)	0.0557 (4)
H5	0.5097	0.0392	0.1721	0.067*
C6	0.4257 (2)	−0.10127 (18)	0.11367 (11)	0.0579 (4)
H6	0.5067	−0.1761	0.1217	0.069*
C7	0.3015 (2)	0.28325 (18)	0.16136 (11)	0.0513 (4)
H7A	0.3025	0.3681	0.1131	0.062*
H7B	0.1946	0.2855	0.2031	0.062*
C8	0.5758 (2)	0.39025 (17)	0.15325 (10)	0.0506 (4)
H8	0.5780	0.4366	0.0964	0.061*
C9	0.7086 (2)	0.41397 (18)	0.18741 (10)	0.0535 (4)
C10	0.6996 (2)	0.34162 (18)	0.27232 (11)	0.0545 (4)
H10	0.7867	0.3563	0.2973	0.065*
C11	0.5642 (2)	0.24809 (17)	0.32079 (10)	0.0502 (4)
C12	0.4356 (2)	0.23031 (17)	0.28237 (9)	0.0481 (4)
H12	0.3430	0.1686	0.3134	0.058*
C13	0.8551 (3)	0.5148 (3)	0.13244 (14)	0.0805 (6)
H13A	0.8947	0.4865	0.0787	0.121*
H13B	0.9460	0.5045	0.1613	0.121*
H13C	0.8178	0.6177	0.1223	0.121*
C14	0.5536 (3)	0.1662 (2)	0.41234 (11)	0.0665 (5)
H14A	0.6636	0.1660	0.4245	0.100*
H14B	0.5168	0.0643	0.4210	0.100*
H14C	0.4735	0.2161	0.4499	0.100*
C15	0.8272 (2)	0.8781 (2)	0.25321 (12)	0.0631 (5)
C16	0.9551 (2)	1.0193 (2)	0.32804 (11)	0.0566 (4)
C17	0.8784 (2)	0.88381 (18)	0.32838 (10)	0.0539 (4)
C18	0.8522 (2)	0.76197 (17)	0.40146 (10)	0.0497 (4)
C19	0.9004 (2)	0.77045 (17)	0.47720 (10)	0.0506 (4)
H19	0.9526	0.8578	0.4785	0.061*
C20	0.8724 (2)	0.65455 (17)	0.54774 (10)	0.0502 (4)
H20	0.9058	0.6646	0.5961	0.060*
C21	0.7936 (2)	0.51845 (17)	0.54952 (10)	0.0502 (4)
C22	0.7464 (2)	0.50974 (18)	0.47347 (11)	0.0588 (4)
H22	0.6953	0.4221	0.4718	0.071*
C23	0.7742 (2)	0.62636 (19)	0.40311 (11)	0.0581 (4)
H23	0.7409	0.6166	0.3547	0.070*
C24	0.7631 (2)	0.39860 (18)	0.62288 (10)	0.0553 (4)
C25	0.7996 (2)	0.41186 (19)	0.70048 (11)	0.0583 (4)
C26	0.6899 (3)	0.2598 (2)	0.62445 (11)	0.0639 (5)
N1	0.3014 (2)	−0.25176 (18)	0.03913 (9)	0.0650 (4)
N2	0.44324 (16)	0.30155 (13)	0.20044 (8)	0.0456 (3)
N3	0.7848 (3)	0.8728 (2)	0.19242 (12)	0.0903 (6)
N4	1.0142 (2)	1.12948 (19)	0.33055 (11)	0.0752 (5)
N5	0.8270 (3)	0.4254 (2)	0.76315 (10)	0.0802 (5)
N6	0.6314 (3)	0.1475 (2)	0.62508 (12)	0.0907 (6)
O1	0.1827 (2)	−0.2699 (2)	0.00906 (11)	0.0984 (5)
O2	0.4200 (2)	−0.33952 (15)	0.04148 (8)	0.0797 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0619 (10)	0.0509 (9)	0.0478 (9)	−0.0093 (7)	−0.0113 (7)	−0.0133 (7)
C2	0.0824 (14)	0.1014 (16)	0.134 (2)	0.0240 (12)	−0.0685 (14)	−0.0698 (15)
C3	0.0792 (14)	0.0869 (14)	0.1301 (19)	0.0341 (11)	−0.0692 (14)	−0.0587 (14)
C4	0.0492 (8)	0.0473 (8)	0.0439 (8)	−0.0011 (6)	−0.0155 (6)	−0.0082 (6)
C5	0.0644 (10)	0.0535 (9)	0.0587 (10)	0.0069 (7)	−0.0338 (8)	−0.0135 (7)
C6	0.0739 (11)	0.0473 (9)	0.0563 (10)	0.0070 (8)	−0.0274 (8)	−0.0089 (7)
C7	0.0539 (9)	0.0485 (8)	0.0569 (9)	0.0028 (7)	−0.0238 (7)	−0.0125 (7)
C8	0.0615 (10)	0.0445 (8)	0.0447 (8)	−0.0022 (7)	−0.0143 (7)	−0.0058 (6)
C9	0.0573 (10)	0.0478 (8)	0.0572 (9)	−0.0040 (7)	−0.0146 (8)	−0.0135 (7)
C10	0.0587 (10)	0.0546 (9)	0.0595 (10)	0.0006 (7)	−0.0241 (8)	−0.0207 (7)
C11	0.0617 (10)	0.0477 (8)	0.0453 (8)	0.0049 (7)	−0.0169 (7)	−0.0156 (7)
C12	0.0552 (9)	0.0449 (8)	0.0443 (8)	−0.0021 (6)	−0.0115 (7)	−0.0107 (6)
C13	0.0729 (13)	0.0809 (14)	0.0830 (14)	−0.0252 (11)	−0.0143 (11)	−0.0090 (11)
C14	0.0828 (13)	0.0734 (12)	0.0456 (9)	−0.0002 (9)	−0.0220 (9)	−0.0113 (8)
C15	0.0654 (11)	0.0626 (11)	0.0613 (11)	0.0035 (8)	−0.0258 (9)	−0.0042 (8)
C16	0.0548 (10)	0.0537 (10)	0.0570 (10)	0.0021 (8)	−0.0132 (8)	−0.0051 (7)
C17	0.0556 (9)	0.0501 (9)	0.0559 (9)	0.0043 (7)	−0.0179 (7)	−0.0083 (7)
C18	0.0522 (9)	0.0460 (8)	0.0529 (9)	0.0062 (7)	−0.0153 (7)	−0.0140 (7)
C19	0.0545 (9)	0.0458 (8)	0.0553 (9)	0.0005 (7)	−0.0146 (7)	−0.0176 (7)
C20	0.0570 (9)	0.0498 (8)	0.0484 (9)	0.0045 (7)	−0.0149 (7)	−0.0186 (7)
C21	0.0578 (9)	0.0460 (8)	0.0496 (9)	0.0056 (7)	−0.0141 (7)	−0.0161 (7)
C22	0.0759 (11)	0.0463 (9)	0.0603 (10)	−0.0065 (8)	−0.0261 (8)	−0.0129 (7)
C23	0.0762 (11)	0.0518 (9)	0.0544 (9)	0.0000 (8)	−0.0294 (8)	−0.0137 (7)
C24	0.0677 (10)	0.0481 (9)	0.0509 (9)	0.0010 (7)	−0.0141 (8)	−0.0130 (7)
C25	0.0734 (11)	0.0492 (9)	0.0490 (10)	0.0027 (8)	−0.0104 (8)	−0.0097 (7)
C26	0.0795 (12)	0.0543 (10)	0.0566 (10)	−0.0027 (9)	−0.0187 (9)	−0.0071 (8)
N1	0.0819 (11)	0.0605 (9)	0.0519 (8)	−0.0165 (8)	−0.0075 (7)	−0.0163 (7)
N2	0.0523 (7)	0.0422 (6)	0.0459 (7)	0.0010 (5)	−0.0171 (6)	−0.0121 (5)
N3	0.0981 (14)	0.1037 (14)	0.0760 (12)	0.0055 (11)	−0.0442 (11)	−0.0116 (10)
N4	0.0802 (11)	0.0611 (10)	0.0811 (11)	−0.0123 (8)	−0.0199 (9)	−0.0071 (8)
N5	0.1159 (15)	0.0736 (11)	0.0536 (9)	0.0017 (10)	−0.0239 (9)	−0.0160 (8)
N6	0.1217 (16)	0.0631 (11)	0.0885 (13)	−0.0249 (10)	−0.0333 (11)	−0.0059 (9)
O1	0.0935 (11)	0.1097 (12)	0.1151 (13)	−0.0195 (9)	−0.0270 (9)	−0.0635 (10)
O2	0.1179 (12)	0.0539 (7)	0.0688 (8)	0.0086 (8)	−0.0227 (8)	−0.0187 (6)

Geometric parameters (Å, º) top

C1—C2	1.356 (3)	C13—H13B	0.960
C1—C6	1.362 (2)	C13—H13C	0.960
C1—N1	1.469 (2)	C14—H14A	0.960
C2—C3	1.372 (3)	C14—H14B	0.960
C2—H2	0.930	C14—H14C	0.960
C3—C4	1.377 (2)	C15—N3	1.151 (2)
C3—H3	0.930	C15—C17	1.416 (2)
C4—C5	1.373 (2)	C16—N4	1.151 (2)
C4—C7	1.508 (2)	C16—C17	1.413 (2)
C5—C6	1.384 (2)	C17—C18	1.416 (2)
C5—H5	0.930	C18—C23	1.412 (2)
C6—H6	0.930	C18—C19	1.419 (2)
C7—N2	1.4818 (19)	C19—C20	1.357 (2)
C7—H7A	0.970	C19—H19	0.930
C7—H7B	0.970	C20—C21	1.419 (2)
C8—N2	1.343 (2)	C20—H20	0.930
C8—C9	1.379 (2)	C21—C24	1.408 (2)
C8—H8	0.930	C21—C22	1.421 (2)
C9—C10	1.388 (2)	C22—C23	1.359 (2)
C9—C13	1.509 (2)	C22—H22	0.930
C10—C11	1.386 (2)	C23—H23	0.930
C10—H10	0.930	C24—C25	1.418 (2)
C11—C12	1.379 (2)	C24—C26	1.420 (3)
C11—C14	1.505 (2)	C25—N5	1.147 (2)
C12—N2	1.3442 (19)	C26—N6	1.150 (2)
C12—H12	0.930	N1—O1	1.220 (2)
C13—H13A	0.960	N1—O2	1.220 (2)

C2—C1—C6	121.58 (16)	H13A—C13—H13C	109.5
C2—C1—N1	118.90 (16)	H13B—C13—H13C	109.5
C6—C1—N1	119.51 (16)	C11—C14—H14A	109.5
C1—C2—C3	119.27 (16)	C11—C14—H14B	109.5
C1—C2—H2	120.4	H14A—C14—H14B	109.5
C3—C2—H2	120.4	C11—C14—H14C	109.5
C2—C3—C4	121.06 (17)	H14A—C14—H14C	109.5
C2—C3—H3	119.5	H14B—C14—H14C	109.5
C4—C3—H3	119.5	N3—C15—C17	179.6 (2)
C5—C4—C3	118.37 (15)	N4—C16—C17	177.63 (19)
C5—C4—C7	124.51 (13)	C16—C17—C15	116.70 (15)
C3—C4—C7	117.11 (14)	C16—C17—C18	120.87 (14)
C4—C5—C6	120.97 (14)	C15—C17—C18	122.42 (15)
C4—C5—H5	119.5	C23—C18—C17	121.56 (14)
C6—C5—H5	119.5	C23—C18—C19	116.56 (14)
C1—C6—C5	118.74 (15)	C17—C18—C19	121.88 (14)
C1—C6—H6	120.6	C20—C19—C18	121.80 (14)
C5—C6—H6	120.6	C20—C19—H19	119.1
N2—C7—C4	113.85 (12)	C18—C19—H19	119.1
N2—C7—H7A	108.8	C19—C20—C21	121.66 (14)
C4—C7—H7A	108.8	C19—C20—H20	119.2
N2—C7—H7B	108.8	C21—C20—H20	119.2
C4—C7—H7B	108.8	C24—C21—C20	121.76 (14)
H7A—C7—H7B	107.7	C24—C21—C22	121.76 (14)
N2—C8—C9	121.24 (14)	C20—C21—C22	116.48 (14)
N2—C8—H8	119.4	C23—C22—C21	121.60 (15)
C9—C8—H8	119.4	C23—C22—H22	119.2
C8—C9—C10	117.15 (15)	C21—C22—H22	119.2
C8—C9—C13	119.71 (16)	C22—C23—C18	121.90 (15)
C10—C9—C13	123.14 (16)	C22—C23—H23	119.1
C11—C10—C9	121.71 (14)	C18—C23—H23	119.1
C11—C10—H10	119.1	C21—C24—C25	121.48 (14)
C9—C10—H10	119.1	C21—C24—C26	122.28 (14)
C12—C11—C10	117.85 (14)	C25—C24—C26	116.22 (15)
C12—C11—C14	119.55 (15)	N5—C25—C24	178.50 (19)
C10—C11—C14	122.60 (15)	N6—C26—C24	179.5 (2)
N2—C12—C11	120.51 (14)	O1—N1—O2	122.89 (16)
N2—C12—H12	119.7	O1—N1—C1	118.57 (17)
C11—C12—H12	119.7	O2—N1—C1	118.52 (15)
C9—C13—H13A	109.5	C8—N2—C12	121.53 (13)
C9—C13—H13B	109.5	C8—N2—C7	119.09 (12)
H13A—C13—H13B	109.5	C12—N2—C7	119.38 (13)
C9—C13—H13C	109.5

C6—C1—C2—C3	1.1 (4)	C23—C18—C19—C20	−0.3 (2)
N1—C1—C2—C3	−178.1 (2)	C17—C18—C19—C20	178.78 (15)
C1—C2—C3—C4	−0.9 (4)	C18—C19—C20—C21	0.1 (2)
C2—C3—C4—C5	−0.1 (3)	C19—C20—C21—C24	−179.44 (15)
C2—C3—C4—C7	−179.1 (2)	C19—C20—C21—C22	0.3 (2)
C3—C4—C5—C6	0.9 (3)	C24—C21—C22—C23	179.20 (16)
C7—C4—C5—C6	179.83 (16)	C20—C21—C22—C23	−0.6 (3)
C2—C1—C6—C5	−0.4 (3)	C21—C22—C23—C18	0.4 (3)
N1—C1—C6—C5	178.90 (15)	C17—C18—C23—C22	−179.01 (16)
C4—C5—C6—C1	−0.7 (3)	C19—C18—C23—C22	0.0 (3)
C5—C4—C7—N2	4.9 (2)	C20—C21—C24—C25	4.2 (3)
C3—C4—C7—N2	−176.16 (17)	C22—C21—C24—C25	−175.56 (16)
N2—C8—C9—C10	0.3 (2)	C20—C21—C24—C26	−177.65 (16)
N2—C8—C9—C13	−179.80 (16)	C22—C21—C24—C26	2.6 (3)
C8—C9—C10—C11	0.7 (2)	C2—C1—N1—O1	−6.9 (3)
C13—C9—C10—C11	−179.16 (17)	C6—C1—N1—O1	173.77 (16)
C9—C10—C11—C12	−1.0 (2)	C2—C1—N1—O2	171.89 (19)
C9—C10—C11—C14	178.76 (15)	C6—C1—N1—O2	−7.4 (2)
C10—C11—C12—N2	0.2 (2)	C9—C8—N2—C12	−1.1 (2)
C14—C11—C12—N2	−179.49 (14)	C9—C8—N2—C7	178.29 (13)
C16—C17—C18—C23	179.39 (16)	C11—C12—N2—C8	0.8 (2)
C15—C17—C18—C23	0.5 (3)	C11—C12—N2—C7	−178.60 (13)
C16—C17—C18—C19	0.4 (2)	C4—C7—N2—C8	99.78 (16)
C15—C17—C18—C19	−178.44 (16)	C4—C7—N2—C12	−80.84 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N2	0.93	2.56	2.895 (2)	102
C7—H7B···N4ⁱ	0.97	2.43	3.245 (3)	141
C8—H8···O2ⁱⁱ	0.93	2.46	3.119 (2)	128

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅N₂O₂⁺·C₁₂H₄N₄⁻
M_r	447.47
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.098 (2), 9.137 (2), 16.542 (4)
α, β, γ (°)	76.194 (3), 75.951 (3), 86.933 (3)
V (Å³)	1153.0 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.18 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.985, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	5765, 3998, 3255
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.144, 1.00
No. of reflections	3998
No. of parameters	309
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.20

Computer programs: SMART (Bruker, 2000), SAINT-Plus (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
C5—H5···N2	0.93	2.56	2.895 (2)	102
C7—H7B···N4ⁱ	0.97	2.43	3.245 (3)	141
C8—H8···O2ⁱⁱ	0.93	2.46	3.119 (2)	128

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China (project Nos. 20371002 and 20771006) and the Natural Science Foundation of the Education Committee of Anhui Province, China (project No. KJ2008B004).

References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Liu, 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
Madalan, A. M., Roesky, H. W., Andruh, M., Noltemeyer, M. & Stanica, N. (2002). Chem. Commun. pp. 1638–1639. Web of Science CSD CrossRef Google Scholar
Ren, 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
Ren, 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
Ren, 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
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, P.-F., Liu, G.-X. & Chen, Y.-C. (2006). Acta Cryst. E62, o3256–o3258. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 64| Part 5| May 2008| Page o798

doi:10.1107/S1600536808008258

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

A charge-transfer salt, 3,5-di­methyl-1-(4-nitro­benz­yl)pyridinium 7,7,8,8-tetra­cyano­quinodi­methane

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

A charge-transfer salt, 3,5-dimethyl-1-(4-nitrobenzyl)pyridinium 7,7,8,8-tetracyanoquinodimethane