A uniform and one-dimensional stacking of 2,5-di­chloro­tetra­cyano­quinodimethanide mol­ecules in the tetra­methyl­arsonium salt

In the tetra­methyl­arsonium salt of 2,5-di­chloro-7,7,8,8-tetra­cyano­quinodimethanide [systematic name: tetra­methyl­arson­ium 2,2'-(2,5-dichlorocyclohexa-2,5-diene-1,4-diylidene)bis(propanedinitrile)], C₄H₁₂As⁺·C₁₂H₂Cl₂N₄^- or [As(CH₃)₄](C₁₂H₂Cl₂N₄), the cation lies disordered about a twofold axis and the radical ion lies about an inversion center forming a uniform [interplanar distance 3.35 (2) Å] and one-dimensional stacking without any slip. The electrical conductivity of the single crystal at room temperature was less than 10^-9 S cm^-1, and the temperature dependence of para­magnetic susceptibility obeyed a one-dimensional antiferromagnetic Heisenberg model with a spin-exchange integral of 83 K in the temperature range 1.8-320.0 K.

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1985a); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1985b); program(s) used to solve structure: SIR92; program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.

(global)

Crystal data

C4H12As^+·C12H2Cl2N4^−	Dx = 1.350 Mg m^−3
Mr = 408.14	Mo Kα radiation, λ = 0.7107 Å
Monoclinic, C2/c	Cell parameters from 24 reflections
a = 11.046 (3) Å	θ = 12.9–14.8°
b = 27.336 (4) Å	µ = 1.96 mm^−1
c = 6.707 (6) Å	T = 296 K
β = 97.45 (4)°	Prismatic, colorless
V = 2007 (1) Å^3	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection

Rigaku AFC-5R diffractometer	Rint = 0.011
ω–2θ scans	θmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = 0→14
Tmin = 0.668, Tmax = 0.675	k = 0→35
2434 measured reflections	l = −8→8
2323 independent reflections	3 standard reflections every 200 reflections
1157 reflections with F^2 > 2σ(F^2)	intensity decay: 10.0%

Refinement

Refinement on F	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.063	w = 1/[σ^2(Fo) + 0.00096|Fo|^2]
wR(F^2) = 0.091	(Δ/σ)max = 0.002
S = 1.95	Δρmax = 0.78 e Å^−3
1157 reflections	Δρmin = −0.28 e Å^−3
114 parameters

Special details

Refinement. Refinement using reflections with F² > 2.0 σ(F²). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
As1	0	0.29698 (4)	0.2500	0.0827 (4)
Cl1	0.2325 (2)	0.06348 (8)	0.5680 (4)	0.1043 (9)
N1	−0.2576 (10)	0.1367 (3)	0.434 (1)	0.116 (3)
N2	0.1098 (9)	0.1767 (2)	0.543 (1)	0.116 (3)
C1	−0.158 (1)	0.1221 (3)	0.459 (1)	0.083 (3)
C2	−0.0376 (9)	0.1040 (3)	0.492 (1)	0.073 (3)
C3	0.0513 (9)	0.1431 (3)	0.522 (1)	0.083 (3)
C4	−0.0162 (8)	0.0515 (2)	0.4961 (10)	0.064 (2)
C5	0.1002 (7)	0.0286 (2)	0.531 (1)	0.065 (2)
C6	−0.1156 (7)	0.0199 (2)	0.466 (1)	0.064 (2)
C7	−0.1269 (9)	0.2608 (3)	0.329 (2)	0.108 (4)
C8	−0.077 (2)	0.3086 (9)	−0.054 (4)	0.137 (10)	0.50
C9	0.044 (2)	0.3504 (9)	0.378 (6)	0.19 (2)	0.50
H1	−0.2088	0.0348	0.4483	0.0816*
H3	−0.2089	0.2813	0.3118	0.1483*
H4	−0.1393	0.2276	0.2357	0.1483*
H5	−0.1034	0.2493	0.4840	0.1483*
H6	−0.1779	0.3251	−0.0401	0.2276*	0.50
H7	−0.0360	0.3285	−0.1335	0.2276*	0.50
H8	−0.1090	0.2714	−0.1179	0.2276*	0.50
H9	0.0849	0.3445	0.5152	0.2208*	0.50
H10	0.1252	0.3646	0.2827	0.2208*	0.50
H11	−0.0217	0.3770	0.3463	0.2208*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
As1	0.0597 (7)	0.0475 (6)	0.144 (1)	0.0000	0.0233 (7)	0.0000
Cl1	0.114 (2)	0.063 (1)	0.134 (2)	−0.015 (1)	0.012 (2)	−0.002 (1)
N1	0.142 (8)	0.081 (5)	0.126 (7)	0.034 (5)	0.017 (6)	0.006 (5)
N2	0.180 (9)	0.049 (4)	0.120 (7)	−0.023 (5)	0.026 (6)	0.003 (4)
C1	0.129 (8)	0.047 (4)	0.075 (6)	0.006 (5)	0.021 (6)	−0.005 (4)
C2	0.121 (7)	0.048 (4)	0.051 (5)	0.008 (4)	0.023 (5)	0.004 (3)
C3	0.134 (8)	0.052 (4)	0.065 (6)	0.000 (5)	0.023 (5)	0.007 (4)
C4	0.111 (6)	0.044 (3)	0.039 (4)	0.006 (4)	0.020 (4)	0.000 (3)
C5	0.096 (6)	0.048 (4)	0.053 (5)	−0.007 (4)	0.011 (4)	0.000 (3)
C6	0.094 (5)	0.043 (3)	0.056 (5)	0.002 (4)	0.015 (4)	−0.003 (4)
C7	0.108 (7)	0.065 (5)	0.164 (10)	−0.016 (5)	0.068 (7)	−0.012 (6)
C8	0.14 (2)	0.13 (2)	0.13 (2)	−0.04 (2)	−0.03 (2)	0.06 (2)
C9	0.14 (3)	0.11 (2)	0.33 (5)	−0.08 (2)	0.10 (3)	−0.12 (2)

Geometric parameters (Å, º)

Cl1—C5	1.735 (8)	C2—C4	1.454 (9)
N1—C1	1.16 (1)	C4—C5	1.42 (1)
N2—C3	1.12 (1)	C4—C6	1.39 (1)
C1—C2	1.41 (1)	C5—C6^i	1.336 (8)
C2—C3	1.45 (1)
N1—C1—C2	179.4 (10)	C2—C4—C6	119.2 (8)
C1—C2—C3	111.8 (7)	C5—C4—C6	115.5 (6)
C1—C2—C4	119.8 (8)	Cl1—C5—C4	120.6 (5)
C3—C2—C4	128.4 (8)	Cl1—C5—C6^i	116.1 (6)
N2—C3—C2	172 (1)	C4—C5—C6^i	123.3 (7)
C2—C4—C5	125.3 (7)	C4—C6—C5^i	121.2 (7)
Cl1—C5—C4—C2	−1 (1)	C2—C4—C5—C6^i	179.6 (7)
Cl1—C5—C4—C6	179.4 (5)	C2—C4—C6—C5^i	−179.7 (7)
Cl1—C5—C6^i—C4^i	−179.5 (5)	C3—C2—C4—C5	0 (1)
C1—C2—C4—C5	−179.0 (7)	C3—C2—C4—C6	179.1 (7)
C1—C2—C4—C6	0 (1)

Symmetry code: (i) −x, −y, −z+1.