An anion–radical salt of 1-(4-cyano­benz­yl)-4-methyl­pyridinium cations and 7,7,8,8-tetra­cyano­quinodimethane anions

In the structure of the title compound, 1-(4-cyano­benzyl)-4-methyl­pyridinium 7,7,8,8-tetra­cyano­quinodimethanide, C₁₄H₁₃N₂⁺·[C₈H₄(CN)₄]⁻, the asymmetric unit contains one cation and one anion. Intra- and inter­molecular C—H...N hydrogen bonds and π–π stacking inter­actions seem to be effective in the stabilization of the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.043
• wR factor = 0.134
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2     -   C3      ..       5.53 su
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C13    -   C14    ...       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C10    -   C12    ...       1.42 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1-(4-cyanobenzyl)-4-methylpyridinium 7,7,8,8-tetracyanoquinodimethanide

Crystal data

C14H13N2^+·C12H4N4^−	Z = 2
Mr = 413.46	F(000) = 430
Triclinic, P1	Dx = 1.287 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3594 (15) Å	Cell parameters from 3394 reflections
b = 11.869 (2) Å	θ = 2.9–25.8°
c = 13.612 (3) Å	µ = 0.08 mm^−1
α = 110.792 (7)°	T = 293 K
β = 95.454 (8)°	Block, dark green
γ = 102.249 (7)°	0.21 × 0.17 × 0.10 mm
V = 1067.3 (4) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3915 independent reflections
Radiation source: sealed tube	2822 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
Tmin = 0.983, Tmax = 0.992	k = −14→14
11982 measured reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0763P)^2 + 0.0151P] where P = (Fo^2 + 2Fc^2)/3
3915 reflections	(Δ/σ)max < 0.001
290 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	−0.0312 (2)	−0.26066 (15)	0.21413 (11)	0.0656 (4)
N2	0.0894 (3)	0.13616 (18)	0.26123 (15)	0.1033 (7)
N3	0.6118 (3)	0.34145 (15)	0.88906 (12)	0.0760 (5)
N4	0.5165 (2)	−0.04620 (15)	0.84754 (12)	0.0716 (5)
N5	0.18247 (18)	0.62180 (12)	0.88204 (9)	0.0490 (3)
N6	0.2705 (3)	0.5510 (2)	0.32688 (17)	0.1027 (7)
C1	0.0388 (2)	−0.15768 (16)	0.26706 (12)	0.0485 (4)
C2	0.1019 (3)	0.05997 (17)	0.29271 (13)	0.0621 (5)
C3	0.1220 (2)	−0.03128 (15)	0.33420 (11)	0.0465 (4)
C4	0.21408 (19)	0.00376 (14)	0.44083 (11)	0.0412 (3)
C5	0.2808 (2)	0.13043 (14)	0.51124 (11)	0.0450 (4)
H5	0.2627	0.1919	0.4868	0.054*
C6	0.3706 (2)	0.16529 (14)	0.61330 (11)	0.0444 (4)
H6	0.4144	0.2498	0.6567	0.053*
C7	0.3988 (2)	0.07528 (13)	0.65492 (11)	0.0417 (3)
C8	0.3282 (2)	−0.05134 (14)	0.58564 (11)	0.0453 (4)
H8	0.3420	−0.1128	0.6110	0.054*
C9	0.2406 (2)	−0.08623 (14)	0.48281 (11)	0.0444 (4)
H9	0.1972	−0.1707	0.4393	0.053*
C10	0.4918 (2)	0.11151 (14)	0.76160 (11)	0.0459 (4)
C11	0.5590 (2)	0.23861 (17)	0.83123 (12)	0.0534 (4)
C12	0.5064 (2)	0.02351 (15)	0.80814 (12)	0.0510 (4)
C13	0.2798 (3)	0.5450 (2)	0.40878 (18)	0.0749 (6)
C14	0.2919 (3)	0.54248 (18)	0.51348 (15)	0.0605 (5)
C15	0.4152 (3)	0.64102 (18)	0.59847 (17)	0.0712 (5)
H15	0.4904	0.7070	0.5868	0.085*
C16	0.4266 (3)	0.64140 (17)	0.69937 (16)	0.0694 (5)
H16	0.5119	0.7067	0.7558	0.083*
C17	0.3119 (2)	0.54515 (16)	0.71831 (13)	0.0545 (4)
C18	0.1926 (2)	0.44579 (16)	0.63363 (14)	0.0546 (4)
H18	0.1184	0.3799	0.6458	0.066*
C19	0.1816 (2)	0.44278 (17)	0.53106 (15)	0.0602 (5)
H19	0.1014	0.3750	0.4741	0.072*
C20	0.3150 (2)	0.55083 (17)	0.83076 (14)	0.0607 (5)
H20A	0.2787	0.4668	0.8294	0.073*
H20B	0.4422	0.5910	0.8721	0.073*
C21	0.2291 (3)	0.74696 (16)	0.91367 (14)	0.0588 (4)
H21	0.3458	0.7881	0.9056	0.071*
C22	0.1086 (3)	0.81365 (15)	0.95695 (14)	0.0593 (5)
H22	0.1437	0.9001	0.9783	0.071*
C23	−0.0665 (2)	0.75543 (14)	0.97014 (11)	0.0484 (4)
C24	−0.1075 (2)	0.62746 (15)	0.93885 (13)	0.0554 (4)
H24	−0.2218	0.5847	0.9480	0.067*
C25	0.0161 (2)	0.56252 (15)	0.89478 (12)	0.0536 (4)
H25	−0.0155	0.4761	0.8733	0.064*
C26	−0.2020 (3)	0.82800 (17)	1.01433 (14)	0.0671 (5)
H26A	−0.2616	0.8496	0.9602	0.101*
H26B	−0.1352	0.9029	1.0744	0.101*
H26C	−0.2965	0.7784	1.0370	0.101*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0807 (10)	0.0497 (10)	0.0525 (9)	0.0062 (8)	0.0018 (7)	0.0123 (8)
N2	0.1373 (17)	0.0764 (13)	0.0953 (13)	0.0120 (12)	−0.0224 (12)	0.0524 (11)
N3	0.1076 (13)	0.0499 (10)	0.0512 (9)	−0.0017 (9)	0.0015 (8)	0.0130 (8)
N4	0.0918 (12)	0.0593 (10)	0.0601 (9)	0.0050 (8)	0.0009 (8)	0.0307 (8)
N5	0.0541 (8)	0.0434 (8)	0.0455 (7)	0.0094 (6)	0.0040 (6)	0.0159 (6)
N6	0.1000 (15)	0.1346 (19)	0.0944 (14)	0.0320 (13)	0.0227 (11)	0.0669 (14)
C1	0.0521 (9)	0.0502 (11)	0.0403 (8)	0.0102 (8)	0.0044 (7)	0.0173 (8)
C2	0.0706 (11)	0.0536 (11)	0.0526 (10)	0.0048 (9)	−0.0079 (8)	0.0208 (9)
C3	0.0495 (8)	0.0429 (9)	0.0436 (8)	0.0081 (7)	0.0046 (6)	0.0162 (7)
C4	0.0397 (8)	0.0387 (9)	0.0425 (8)	0.0077 (6)	0.0088 (6)	0.0138 (7)
C5	0.0510 (8)	0.0375 (9)	0.0473 (8)	0.0105 (7)	0.0094 (7)	0.0178 (7)
C6	0.0515 (9)	0.0338 (8)	0.0434 (8)	0.0075 (7)	0.0109 (7)	0.0113 (7)
C7	0.0433 (8)	0.0393 (9)	0.0396 (8)	0.0077 (6)	0.0117 (6)	0.0127 (7)
C8	0.0541 (9)	0.0374 (9)	0.0448 (8)	0.0119 (7)	0.0084 (7)	0.0167 (7)
C9	0.0496 (8)	0.0333 (8)	0.0444 (8)	0.0074 (6)	0.0055 (6)	0.0109 (7)
C10	0.0536 (9)	0.0409 (9)	0.0374 (8)	0.0045 (7)	0.0086 (6)	0.0129 (7)
C11	0.0660 (10)	0.0477 (11)	0.0389 (9)	0.0027 (8)	0.0062 (7)	0.0159 (8)
C12	0.0575 (10)	0.0461 (10)	0.0403 (8)	0.0022 (7)	0.0043 (7)	0.0138 (8)
C13	0.0690 (12)	0.0909 (16)	0.0853 (14)	0.0349 (11)	0.0268 (10)	0.0468 (13)
C14	0.0615 (11)	0.0646 (12)	0.0737 (12)	0.0325 (10)	0.0289 (9)	0.0348 (10)
C15	0.0779 (13)	0.0532 (12)	0.0906 (14)	0.0192 (10)	0.0415 (11)	0.0296 (11)
C16	0.0680 (12)	0.0532 (12)	0.0748 (13)	0.0057 (9)	0.0247 (10)	0.0134 (10)
C17	0.0513 (9)	0.0477 (10)	0.0645 (11)	0.0170 (8)	0.0161 (8)	0.0181 (9)
C18	0.0510 (9)	0.0490 (10)	0.0666 (11)	0.0126 (8)	0.0136 (8)	0.0253 (9)
C19	0.0535 (10)	0.0574 (11)	0.0680 (11)	0.0177 (8)	0.0101 (8)	0.0207 (9)
C20	0.0591 (10)	0.0569 (11)	0.0654 (11)	0.0196 (9)	0.0069 (8)	0.0216 (9)
C21	0.0601 (10)	0.0443 (10)	0.0677 (11)	0.0035 (8)	0.0112 (8)	0.0228 (9)
C22	0.0721 (11)	0.0356 (9)	0.0662 (11)	0.0087 (8)	0.0082 (9)	0.0193 (8)
C23	0.0601 (10)	0.0427 (9)	0.0375 (8)	0.0101 (7)	0.0011 (7)	0.0136 (7)
C24	0.0567 (10)	0.0448 (10)	0.0577 (10)	0.0038 (8)	0.0092 (8)	0.0174 (8)
C25	0.0607 (10)	0.0365 (9)	0.0539 (10)	0.0034 (8)	0.0048 (8)	0.0129 (8)
C26	0.0748 (12)	0.0588 (12)	0.0641 (11)	0.0231 (10)	0.0086 (9)	0.0174 (9)

Geometric parameters (Å, º)

N1—C1	1.147 (2)	C14—C15	1.385 (3)
N2—C2	1.146 (2)	C14—C19	1.395 (3)
N3—C11	1.149 (2)	C15—C16	1.366 (3)
N4—C12	1.145 (2)	C15—H15	0.9300
N5—C25	1.336 (2)	C16—C17	1.387 (3)
N5—C21	1.346 (2)	C16—H16	0.9300
N5—C20	1.486 (2)	C17—C18	1.376 (2)
N6—C13	1.138 (2)	C17—C20	1.506 (2)
C1—C3	1.411 (2)	C18—C19	1.378 (2)
C2—C3	1.414 (2)	C18—H18	0.9300
C3—C4	1.4156 (19)	C19—H19	0.9300
C4—C5	1.412 (2)	C20—H20A	0.9700
C4—C9	1.416 (2)	C20—H20B	0.9700
C5—C6	1.356 (2)	C21—C22	1.352 (2)
C5—H5	0.9300	C21—H21	0.9300
C6—C7	1.417 (2)	C22—C23	1.387 (2)
C6—H6	0.9300	C22—H22	0.9300
C7—C8	1.410 (2)	C23—C24	1.379 (2)
C7—C10	1.416 (2)	C23—C26	1.486 (2)
C8—C9	1.360 (2)	C24—C25	1.362 (2)
C8—H8	0.9300	C24—H24	0.9300
C9—H9	0.9300	C25—H25	0.9300
C10—C11	1.414 (2)	C26—H26A	0.9600
C10—C12	1.417 (2)	C26—H26B	0.9600
C13—C14	1.431 (3)	C26—H26C	0.9600
C25—N5—C21	119.79 (14)	C15—C16—H16	119.7
C25—N5—C20	120.75 (14)	C17—C16—H16	119.7
C21—N5—C20	119.45 (14)	C18—C17—C16	119.39 (16)
N1—C1—C3	178.49 (17)	C18—C17—C20	120.33 (15)
N2—C2—C3	178.20 (19)	C16—C17—C20	120.26 (16)
C1—C3—C2	117.44 (13)	C17—C18—C19	120.79 (16)
C1—C3—C4	121.52 (13)	C17—C18—H18	119.6
C2—C3—C4	120.97 (14)	C19—C18—H18	119.6
C5—C4—C3	121.48 (13)	C18—C19—C14	119.33 (17)
C5—C4—C9	116.72 (13)	C18—C19—H19	120.3
C3—C4—C9	121.79 (14)	C14—C19—H19	120.3
C6—C5—C4	122.08 (13)	N5—C20—C17	110.38 (12)
C6—C5—H5	119.0	N5—C20—H20A	109.6
C4—C5—H5	119.0	C17—C20—H20A	109.6
C5—C6—C7	121.16 (13)	N5—C20—H20B	109.6
C5—C6—H6	119.4	C17—C20—H20B	109.6
C7—C6—H6	119.4	H20A—C20—H20B	108.1
C8—C7—C10	121.87 (13)	N5—C21—C22	120.83 (16)
C8—C7—C6	116.89 (13)	N5—C21—H21	119.6
C10—C7—C6	121.23 (13)	C22—C21—H21	119.6
C9—C8—C7	121.92 (13)	C21—C22—C23	121.14 (16)
C9—C8—H8	119.0	C21—C22—H22	119.4
C7—C8—H8	119.0	C23—C22—H22	119.4
C8—C9—C4	121.21 (14)	C24—C23—C22	116.31 (15)
C8—C9—H9	119.4	C24—C23—C26	122.41 (16)
C4—C9—H9	119.4	C22—C23—C26	121.28 (15)
C11—C10—C7	121.56 (13)	C25—C24—C23	121.28 (16)
C11—C10—C12	115.87 (13)	C25—C24—H24	119.4
C7—C10—C12	122.29 (14)	C23—C24—H24	119.4
N3—C11—C10	178.80 (18)	N5—C25—C24	120.62 (15)
N4—C12—C10	178.52 (18)	N5—C25—H25	119.7
N6—C13—C14	177.9 (2)	C24—C25—H25	119.7
C15—C14—C19	119.76 (17)	C23—C26—H26A	109.5
C15—C14—C13	119.17 (17)	C23—C26—H26B	109.5
C19—C14—C13	121.08 (19)	H26A—C26—H26B	109.5
C16—C15—C14	120.07 (17)	C23—C26—H26C	109.5
C16—C15—H15	120.0	H26A—C26—H26C	109.5
C14—C15—H15	120.0	H26B—C26—H26C	109.5
C15—C16—C17	120.57 (18)
C1—C3—C4—C5	−173.66 (14)	C15—C16—C17—C18	3.1 (3)
C2—C3—C4—C5	3.2 (2)	C15—C16—C17—C20	−175.53 (16)
C1—C3—C4—C9	5.1 (2)	C16—C17—C18—C19	−2.0 (2)
C2—C3—C4—C9	−178.07 (15)	C20—C17—C18—C19	176.64 (14)
C3—C4—C5—C6	−179.47 (14)	C17—C18—C19—C14	−0.6 (2)
C9—C4—C5—C6	1.7 (2)	C15—C14—C19—C18	2.1 (2)
C4—C5—C6—C7	−1.1 (2)	C13—C14—C19—C18	−177.78 (15)
C5—C6—C7—C8	−0.4 (2)	C25—N5—C20—C17	104.62 (16)
C5—C6—C7—C10	−179.75 (14)	C21—N5—C20—C17	−73.84 (18)
C10—C7—C8—C9	−179.32 (14)	C18—C17—C20—N5	−92.78 (18)
C6—C7—C8—C9	1.3 (2)	C16—C17—C20—N5	85.84 (19)
C7—C8—C9—C4	−0.7 (2)	C25—N5—C21—C22	−0.9 (2)
C5—C4—C9—C8	−0.8 (2)	C20—N5—C21—C22	177.55 (14)
C3—C4—C9—C8	−179.58 (14)	N5—C21—C22—C23	0.0 (3)
C8—C7—C10—C11	−178.82 (14)	C21—C22—C23—C24	1.3 (2)
C6—C7—C10—C11	0.5 (2)	C21—C22—C23—C26	−177.94 (15)
C8—C7—C10—C12	−5.2 (2)	C22—C23—C24—C25	−1.8 (2)
C6—C7—C10—C12	174.07 (14)	C26—C23—C24—C25	177.46 (14)
C19—C14—C15—C16	−1.0 (3)	C21—N5—C25—C24	0.5 (2)
C13—C14—C15—C16	178.88 (16)	C20—N5—C25—C24	−178.00 (14)
C14—C15—C16—C17	−1.6 (3)	C23—C24—C25—N5	0.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20A···N1^i	0.97	2.56	3.436 (3)	151
C21—H21···N4^ii	0.93	2.51	3.322 (3)	146
C25—H25···N1^i	0.93	2.52	3.388 (3)	155

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