A charge-transfer salt, 3,5-dimethyl-1-(4-nitro-benz-yl)pyridinium 7,7,8,8-tetra-cyano-quinodimethane.

In the title salt, C(14)H(15)N(2)O(2) (+)·C(12)H(4)N(4) (-), 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 inter-actions (inter-planar 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 = 447.47

Triclinic,

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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.144

S = 1.00

3998 reflections

309 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.20 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008258/cf2189sup1.cif

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

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

C14H15N2O2+·C12H4N4–	Z = 2
Mr = 447.47	F000 = 466
Triclinic, P1	Dx = 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 = 2.3–27.9º
c = 16.542 (4) Å	µ = 0.09 mm−1
α = 76.194 (3)º	T = 293 (2) K
β = 75.951 (3)º	Pillar, purple
γ = 86.933 (3)º	0.18 × 0.12 × 0.10 mm
V = 1153.0 (5) Å3

Bruker SMART APEX CCD diffractometer	3998 independent reflections
Radiation source: sealed tube	3255 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.018
T = 293(2) K	θmax = 25.1º
φ and ω scans	θmin = 2.3º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −9→9
Tmin = 0.985, Tmax = 0.992	k = −10→10
5765 measured reflections	l = −19→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H-atom parameters constrained
wR(F2) = 0.144	w = 1/[σ2(Fo2) + (0.0904P)2 + 0.1284P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
3998 reflections	Δρmax = 0.15 e Å−3
309 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
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)

	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)

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)

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

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) ; (ii) .