1-(3,4-Dichloro-benz-yl)-3-methyl-quinolin-1-ium 7,7,8,8-tetra-cyano-quinodimethanide.

In the title salt, C(17)H(14)Cl(2)N(+)·C(12)H(4)N(4) (-), cations and anions stack along the a axis into segregated columns by π-π stacking inter-actions, with alternating centroid-centroid separations of 3.5957 (7) and 3.7525 (7) Å for the cation column and 3.4252 (6) and 4.1578 (7) Å for the anion column. In the cation, the dihedral angle between the benzene ring and the quinoline ring system is 76.35 (4)°. The crystal packing is stabilized by inter-columnar 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 ▶); 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

Crystal data

C17H14Cl2N+·C12H4N4 −

M = 507.38

Monoclinic,

a = 7.0795 (14) Å

b = 18.704 (4) Å

c = 18.608 (4) Å

β = 95.286 (2)°

V = 2453.4 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 293 K

0.26 × 0.16 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.928, T max = 0.966

18184 measured reflections

4580 independent reflections

3680 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.101

S = 1.03

4580 reflections

326 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.29 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810002862/rz2411sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002862/rz2411Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H14Cl2N+·C12H4N4−	F(000) = 1044
Mr = 507.38	Dx = 1.374 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7732 reflections
a = 7.0795 (14) Å	θ = 2.4–27.6°
b = 18.704 (4) Å	µ = 0.29 mm−1
c = 18.608 (4) Å	T = 293 K
β = 95.286 (2)°	Block, black
V = 2453.4 (9) Å3	0.26 × 0.16 × 0.12 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	4580 independent reflections
Radiation source: sealed tube	3680 reflections with I > 2σ(I)
graphite	Rint = 0.027
phi and ω scans	θmax = 25.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
Tmin = 0.928, Tmax = 0.966	k = −22→22
18184 measured reflections	l = −22→22

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0415P)2 + 0.9033P] where P = (Fo2 + 2Fc2)/3
4580 reflections	(Δ/σ)max = 0.001
326 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
N5	0.29919 (19)	0.47148 (7)	0.39305 (7)	0.0366 (3)
N1	−0.0533 (2)	0.39215 (9)	0.75827 (9)	0.0550 (4)
N3	0.4950 (3)	0.53355 (8)	1.21413 (9)	0.0536 (4)
N4	0.3739 (3)	0.70369 (9)	1.04907 (11)	0.0700 (5)
N2	0.0918 (3)	0.22596 (9)	0.91236 (10)	0.0730 (6)
Cl1	−0.08219 (9)	0.19603 (3)	0.25897 (3)	0.06871 (18)
Cl2	−0.40722 (9)	0.30060 (3)	0.19589 (4)	0.0817 (2)
C4	0.1467 (2)	0.41286 (9)	0.93789 (9)	0.0392 (4)
C5	0.1399 (2)	0.48648 (9)	0.92029 (9)	0.0402 (4)
H5	0.0852	0.5004	0.8751	0.048*
C7	0.2918 (2)	0.51917 (9)	1.03746 (9)	0.0368 (4)
C28	0.2600 (2)	0.45003 (9)	0.46162 (9)	0.0366 (4)
C17	0.1152 (3)	0.31440 (9)	0.29677 (9)	0.0433 (4)
H17	0.2095	0.2834	0.3158	0.052*
C12	0.4384 (3)	0.55209 (9)	1.15743 (10)	0.0407 (4)
C20	0.3127 (2)	0.54043 (9)	0.37601 (9)	0.0398 (4)
H20	0.3386	0.5524	0.3294	0.048*
C23	0.2461 (2)	0.50382 (10)	0.51399 (9)	0.0405 (4)
C8	0.2976 (2)	0.44532 (9)	1.05546 (9)	0.0408 (4)
H8	0.3498	0.4315	1.1010	0.049*
C21	0.2898 (2)	0.59540 (9)	0.42521 (10)	0.0432 (4)
C1	0.0043 (3)	0.37834 (9)	0.81630 (10)	0.0427 (4)
C10	0.3650 (2)	0.57206 (9)	1.08701 (9)	0.0386 (4)
C6	0.2107 (2)	0.53737 (9)	0.96747 (9)	0.0386 (4)
H6	0.2059	0.5851	0.9535	0.046*
C16	0.1436 (2)	0.38756 (9)	0.30184 (9)	0.0378 (4)
C27	0.2366 (2)	0.37768 (9)	0.47945 (10)	0.0435 (4)
H27	0.2430	0.3423	0.4446	0.052*
C19	0.3282 (2)	0.41725 (9)	0.33621 (9)	0.0407 (4)
H19A	0.4048	0.3784	0.3575	0.049*
H19B	0.3972	0.4391	0.2992	0.049*
C18	−0.0524 (3)	0.28720 (9)	0.26362 (10)	0.0451 (4)
C14	−0.1659 (3)	0.40587 (10)	0.24047 (10)	0.0497 (5)
H14	−0.2606	0.4368	0.2216	0.060*
C22	0.2612 (2)	0.57597 (10)	0.49425 (10)	0.0453 (4)
H22	0.2514	0.6113	0.5289	0.054*
C11	0.3706 (3)	0.64519 (10)	1.06735 (10)	0.0454 (4)
C9	0.2293 (3)	0.39456 (9)	1.00816 (9)	0.0430 (4)
H9	0.2365	0.3467	1.0218	0.052*
C13	−0.1939 (3)	0.33322 (10)	0.23607 (10)	0.0480 (5)
C2	0.0867 (3)	0.28632 (10)	0.90231 (10)	0.0506 (5)
C3	0.0775 (3)	0.36059 (9)	0.88739 (9)	0.0434 (4)
C24	0.2156 (3)	0.48249 (12)	0.58499 (10)	0.0517 (5)
H24	0.2092	0.5169	0.6207	0.062*
C15	0.0019 (3)	0.43294 (9)	0.27275 (9)	0.0450 (4)
H15	0.0202	0.4821	0.2751	0.054*
C25	0.1956 (3)	0.41215 (12)	0.60159 (10)	0.0554 (5)
H25	0.1759	0.3988	0.6485	0.066*
C26	0.2045 (3)	0.35999 (11)	0.54832 (10)	0.0523 (5)
H26	0.1882	0.3122	0.5601	0.063*
C29	0.2965 (3)	0.67200 (10)	0.40124 (12)	0.0608 (6)
H29A	0.2461	0.7022	0.4366	0.091*
H29B	0.2222	0.6775	0.3558	0.091*
H29C	0.4256	0.6853	0.3961	0.091*

	U11	U22	U33	U12	U13	U23
N5	0.0368 (8)	0.0358 (8)	0.0364 (7)	−0.0013 (6)	−0.0005 (6)	−0.0012 (6)
N1	0.0675 (11)	0.0504 (10)	0.0451 (10)	0.0036 (8)	−0.0050 (8)	−0.0007 (7)
N3	0.0688 (11)	0.0444 (9)	0.0465 (9)	0.0067 (8)	0.0004 (8)	0.0009 (7)
N4	0.0915 (15)	0.0396 (10)	0.0773 (13)	0.0033 (9)	−0.0012 (11)	0.0034 (9)
N2	0.1053 (16)	0.0408 (10)	0.0680 (12)	−0.0153 (10)	−0.0177 (11)	0.0083 (9)
Cl1	0.0850 (4)	0.0364 (3)	0.0817 (4)	−0.0103 (2)	−0.0086 (3)	−0.0031 (2)
Cl2	0.0627 (4)	0.0787 (4)	0.0976 (5)	−0.0133 (3)	−0.0252 (3)	−0.0025 (3)
C4	0.0411 (9)	0.0382 (9)	0.0382 (9)	−0.0040 (7)	0.0033 (7)	0.0021 (7)
C5	0.0450 (10)	0.0390 (9)	0.0363 (9)	0.0000 (8)	0.0018 (7)	0.0061 (7)
C7	0.0342 (9)	0.0363 (9)	0.0404 (9)	0.0004 (7)	0.0054 (7)	0.0012 (7)
C28	0.0310 (9)	0.0427 (9)	0.0353 (9)	−0.0002 (7)	−0.0012 (7)	0.0009 (7)
C17	0.0523 (11)	0.0343 (9)	0.0423 (10)	0.0044 (8)	−0.0010 (8)	0.0025 (7)
C12	0.0442 (10)	0.0334 (9)	0.0447 (10)	0.0002 (7)	0.0054 (8)	−0.0046 (8)
C20	0.0396 (9)	0.0380 (9)	0.0404 (9)	−0.0035 (7)	−0.0044 (7)	0.0026 (7)
C23	0.0328 (9)	0.0492 (10)	0.0384 (9)	−0.0004 (7)	−0.0030 (7)	−0.0046 (8)
C8	0.0460 (10)	0.0397 (9)	0.0359 (9)	−0.0007 (8)	−0.0010 (7)	0.0052 (7)
C21	0.0403 (10)	0.0379 (9)	0.0489 (10)	−0.0017 (7)	−0.0092 (8)	−0.0015 (8)
C1	0.0473 (10)	0.0361 (9)	0.0441 (11)	−0.0029 (8)	0.0015 (8)	−0.0026 (8)
C10	0.0391 (9)	0.0361 (9)	0.0407 (9)	0.0011 (7)	0.0034 (7)	−0.0001 (7)
C6	0.0416 (9)	0.0333 (9)	0.0410 (9)	0.0004 (7)	0.0046 (7)	0.0058 (7)
C16	0.0459 (10)	0.0363 (9)	0.0314 (8)	0.0009 (7)	0.0037 (7)	−0.0006 (7)
C27	0.0433 (10)	0.0419 (10)	0.0446 (10)	−0.0002 (8)	0.0008 (8)	0.0021 (8)
C19	0.0451 (10)	0.0389 (9)	0.0385 (9)	0.0009 (8)	0.0059 (8)	−0.0023 (7)
C18	0.0584 (11)	0.0331 (9)	0.0430 (10)	−0.0028 (8)	0.0006 (8)	−0.0006 (7)
C14	0.0530 (11)	0.0450 (11)	0.0497 (11)	0.0096 (9)	−0.0031 (9)	0.0058 (8)
C22	0.0395 (10)	0.0472 (11)	0.0476 (11)	0.0007 (8)	−0.0056 (8)	−0.0137 (8)
C11	0.0501 (11)	0.0392 (10)	0.0461 (10)	0.0029 (8)	−0.0004 (8)	−0.0043 (8)
C9	0.0545 (11)	0.0326 (9)	0.0411 (10)	−0.0022 (8)	0.0004 (8)	0.0063 (7)
C13	0.0489 (11)	0.0495 (11)	0.0440 (10)	−0.0041 (9)	−0.0034 (8)	−0.0010 (8)
C2	0.0652 (13)	0.0429 (11)	0.0415 (10)	−0.0122 (9)	−0.0072 (9)	0.0021 (8)
C3	0.0531 (11)	0.0378 (9)	0.0385 (9)	−0.0062 (8)	0.0004 (8)	0.0039 (7)
C24	0.0445 (11)	0.0706 (14)	0.0395 (10)	0.0008 (9)	0.0004 (8)	−0.0085 (9)
C15	0.0563 (11)	0.0333 (9)	0.0448 (10)	0.0022 (8)	0.0005 (8)	0.0018 (8)
C25	0.0482 (11)	0.0777 (15)	0.0402 (10)	0.0005 (10)	0.0042 (8)	0.0125 (10)
C26	0.0477 (11)	0.0560 (12)	0.0530 (12)	0.0001 (9)	0.0040 (9)	0.0145 (9)
C29	0.0718 (14)	0.0380 (10)	0.0697 (14)	−0.0017 (10)	−0.0090 (11)	−0.0013 (10)

N5—C20	1.334 (2)	C8—H8	0.9300
N5—C28	1.390 (2)	C21—C22	1.368 (3)
N5—C19	1.493 (2)	C21—C29	1.502 (3)
N1—C1	1.148 (2)	C1—C3	1.415 (2)
N3—C12	1.147 (2)	C10—C11	1.417 (2)
N4—C11	1.147 (2)	C6—H6	0.9300
N2—C2	1.144 (2)	C16—C15	1.386 (2)
Cl1—C18	1.7195 (18)	C16—C19	1.507 (2)
Cl2—C13	1.7334 (19)	C27—C26	1.363 (3)
C4—C3	1.412 (2)	C27—H27	0.9300
C4—C5	1.415 (2)	C19—H19A	0.9700
C4—C9	1.424 (2)	C19—H19B	0.9700
C5—C6	1.359 (2)	C18—C13	1.383 (3)
C5—H5	0.9300	C14—C13	1.374 (3)
C7—C6	1.416 (2)	C14—C15	1.377 (3)
C7—C10	1.418 (2)	C14—H14	0.9300
C7—C8	1.421 (2)	C22—H22	0.9300
C28—C27	1.407 (2)	C9—H9	0.9300
C28—C23	1.410 (2)	C2—C3	1.417 (3)
C17—C16	1.385 (2)	C24—C25	1.362 (3)
C17—C18	1.382 (3)	C24—H24	0.9300
C17—H17	0.9300	C15—H15	0.9300
C12—C10	1.415 (2)	C25—C26	1.396 (3)
C20—C21	1.396 (2)	C25—H25	0.9300
C20—H20	0.9300	C26—H26	0.9300
C23—C22	1.405 (3)	C29—H29A	0.9600
C23—C24	1.416 (3)	C29—H29B	0.9600
C8—C9	1.353 (2)	C29—H29C	0.9600
C20—N5—C28	121.49 (14)	N5—C19—C16	112.36 (14)
C20—N5—C19	118.10 (14)	N5—C19—H19A	109.1
C28—N5—C19	120.42 (14)	C16—C19—H19A	109.1
C3—C4—C5	121.14 (15)	N5—C19—H19B	109.1
C3—C4—C9	122.19 (15)	C16—C19—H19B	109.1
C5—C4—C9	116.67 (15)	H19A—C19—H19B	107.9
C6—C5—C4	121.95 (16)	C13—C18—C17	119.92 (17)
C6—C5—H5	119.0	C13—C18—Cl1	121.14 (15)
C4—C5—H5	119.0	C17—C18—Cl1	118.93 (14)
C6—C7—C10	121.57 (15)	C13—C14—C15	120.20 (17)
C6—C7—C8	116.82 (15)	C13—C14—H14	119.9
C10—C7—C8	121.61 (15)	C15—C14—H14	119.9
N5—C28—C27	122.15 (15)	C21—C22—C23	121.46 (16)
N5—C28—C23	117.45 (15)	C21—C22—H22	119.3
C27—C28—C23	120.40 (16)	C23—C22—H22	119.3
C16—C17—C18	120.48 (16)	N4—C11—C10	177.7 (2)
C16—C17—H17	119.8	C8—C9—C4	121.36 (16)
C18—C17—H17	119.8	C8—C9—H9	119.3
N3—C12—C10	177.57 (19)	C4—C9—H9	119.3
N5—C20—C21	122.75 (17)	C14—C13—C18	119.85 (17)
N5—C20—H20	118.6	C14—C13—Cl2	119.25 (15)
C21—C20—H20	118.6	C18—C13—Cl2	120.89 (15)
C22—C23—C28	119.52 (16)	N2—C2—C3	178.0 (2)
C22—C23—C24	122.44 (17)	C4—C3—C1	122.31 (16)
C28—C23—C24	118.04 (17)	C4—C3—C2	122.77 (16)
C9—C8—C7	121.86 (16)	C1—C3—C2	114.80 (15)
C9—C8—H8	119.1	C25—C24—C23	120.81 (18)
C7—C8—H8	119.1	C25—C24—H24	119.6
C22—C21—C20	117.16 (16)	C23—C24—H24	119.6
C22—C21—C29	122.93 (17)	C14—C15—C16	120.64 (17)
C20—C21—C29	119.91 (17)	C14—C15—H15	119.7
N1—C1—C3	179.1 (2)	C16—C15—H15	119.7
C12—C10—C7	119.95 (15)	C24—C25—C26	120.09 (18)
C12—C10—C11	118.51 (15)	C24—C25—H25	120.0
C7—C10—C11	121.52 (15)	C26—C25—H25	120.0
C5—C6—C7	121.33 (15)	C27—C26—C25	121.35 (19)
C5—C6—H6	119.3	C27—C26—H26	119.3
C7—C6—H6	119.3	C25—C26—H26	119.3
C17—C16—C15	118.89 (16)	C21—C29—H29A	109.5
C17—C16—C19	120.51 (15)	C21—C29—H29B	109.5
C15—C16—C19	120.56 (15)	H29A—C29—H29B	109.5
C26—C27—C28	119.26 (18)	C21—C29—H29C	109.5
C26—C27—H27	120.4	H29A—C29—H29C	109.5
C28—C27—H27	120.4	H29B—C29—H29C	109.5
C3—C4—C5—C6	−178.09 (17)	C17—C16—C19—N5	−128.65 (17)
C9—C4—C5—C6	0.9 (3)	C15—C16—C19—N5	53.4 (2)
C20—N5—C28—C27	177.01 (15)	C16—C17—C18—C13	−0.8 (3)
C19—N5—C28—C27	−3.2 (2)	C16—C17—C18—Cl1	−179.64 (14)
C20—N5—C28—C23	−3.7 (2)	C20—C21—C22—C23	−3.1 (3)
C19—N5—C28—C23	176.08 (14)	C29—C21—C22—C23	176.76 (17)
C28—N5—C20—C21	0.3 (2)	C28—C23—C22—C21	−0.2 (3)
C19—N5—C20—C21	−179.46 (15)	C24—C23—C22—C21	−179.69 (16)
N5—C28—C23—C22	3.6 (2)	C7—C8—C9—C4	−0.4 (3)
C27—C28—C23—C22	−177.06 (16)	C3—C4—C9—C8	178.97 (18)
N5—C28—C23—C24	−176.92 (15)	C5—C4—C9—C8	0.0 (3)
C27—C28—C23—C24	2.4 (2)	C15—C14—C13—C18	−0.5 (3)
C6—C7—C8—C9	0.1 (3)	C15—C14—C13—Cl2	179.42 (15)
C10—C7—C8—C9	−179.46 (17)	C17—C18—C13—C14	1.3 (3)
N5—C20—C21—C22	3.1 (3)	Cl1—C18—C13—C14	−179.92 (15)
N5—C20—C21—C29	−176.72 (16)	C17—C18—C13—Cl2	−178.67 (15)
C6—C7—C10—C12	177.58 (16)	Cl1—C18—C13—Cl2	0.1 (2)
C8—C7—C10—C12	−2.9 (3)	C5—C4—C3—C1	2.3 (3)
C6—C7—C10—C11	−3.8 (3)	C9—C4—C3—C1	−176.66 (18)
C8—C7—C10—C11	175.72 (17)	C5—C4—C3—C2	178.20 (18)
C4—C5—C6—C7	−1.3 (3)	C9—C4—C3—C2	−0.7 (3)
C10—C7—C6—C5	−179.66 (16)	C22—C23—C24—C25	177.83 (18)
C8—C7—C6—C5	0.8 (3)	C28—C23—C24—C25	−1.6 (3)
C18—C17—C16—C15	−0.4 (3)	C13—C14—C15—C16	−0.7 (3)
C18—C17—C16—C19	−178.37 (16)	C17—C16—C15—C14	1.1 (3)
N5—C28—C27—C26	177.88 (16)	C19—C16—C15—C14	179.13 (17)
C23—C28—C27—C26	−1.4 (3)	C23—C24—C25—C26	−0.1 (3)
C20—N5—C19—C16	−100.94 (17)	C28—C27—C26—C25	−0.4 (3)
C28—N5—C19—C16	79.31 (18)	C24—C25—C26—C27	1.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···N3i	0.93	2.53	3.387 (3)	154
C19—H19B···N3i	0.97	2.51	3.432 (2)	158
C14—H14···N3ii	0.93	2.50	3.390 (3)	161
C15—H15···N1iii	0.93	2.45	3.348 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯N3i	0.93	2.53	3.387 (3)	154
C19—H19B⋯N3i	0.97	2.51	3.432 (2)	158
C14—H14⋯N3ii	0.93	2.50	3.390 (3)	161
C15—H15⋯N1iii	0.93	2.45	3.348 (2)	163

Symmetry codes: (i) ; (ii) ; (iii) .