Crystal structures of 2,2′-bipyridin-1-ium 1,1,3,3-tetracyano-2-ethoxyprop-2-en-1-ide and bis(2,2′-bipyridin-1-ium) 1,1,3,3-tetracyano-2-(dicyanomethylene)propane-1,3-diide

Setifi, Z.; Valkonen, A.; Fernandes, M.A.; Nummelin, S.; Boughzala, H.; Setifi, F.; Glidewell, C.

doi:10.1107/S2056989015007306

Crystal structures of 2,2′-bipyridin-1-ium 1,1,3,3-tetracyano-2-ethoxyprop-2-en-1-ide and bis(2,2′-bipyridin-1-ium) 1,1,3,3-tetracyano-2-(dicyanomethylene)propane-1,3-diide

Z. Setifi, A. Valkonen, M. A. Fernandes, S. Nummelin, H. Boughzala, F. Setifi and C. Glidewell

In each of the title compounds, the anion shows evidence of extensive electronic delocalization. A combination of N—H

N and X—H

N hydrogen bonds links the ions in (I) into a ribbon of alternating centrosymmetric $R_{4}^{4}$ (18) and $R_{4}^{4}$ (26) rings, and those in (II) into simple $C_{2}^{1}$ (7) chains of alternating cations and anion with further cations pendent from the chain.

Keywords: crystal structure; bipyridinium cations; polynitrile anions; molecular conformation; hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015007306/hb7404sup1.cif Contains datablocks global, I, II
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989015007306/hb7404Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989015007306/hb7404IIsup3.hkl Contains datablock II
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015007306/hb7404Isup4.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015007306/hb7404IIsup5.cml Supplementary material

CCDC references: 1059034; 1059033

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.002 Å
Disorder in main residue
R factor = 0.042
wR factor = 0.103
Data-to-parameter ratio = 16.0

Structure: II

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.006 Å
R factor = 0.067
wR factor = 0.183
Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.608 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         21 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....         11 Note

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          6 Note
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00100 Degree
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          1 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C31    --  C311    ..        6.2 su
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C31    --  C312    ..        6.6 su
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C33    --  C331    ..        7.0 su
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C33    --  C332    ..        5.1 su
PLAT300_ALERT_4_G Atom Site Occupancy of >O321   is Constrained at      0.634 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <O341   is Constrained at      0.366 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >C321   is Constrained at      0.634 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >C322   is Constrained at      0.634 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C341   is Constrained at      0.366 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C342   is Constrained at      0.366 Check
PLAT301_ALERT_3_G Main Residue  Disorder ............ Percentage =         12 Note
PLAT789_ALERT_4_G Atoms with Negative _atom_site_disorder_group  #         16 Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          3 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          3 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         57 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  19 ALERT level G = General information/check it is not something unexpected

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




Datablock: II


Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         46 %
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0058 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     11.618 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.399 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          2 Report

Alert level G
PLAT112_ALERT_2_G ADDSYM Detects Additional (Pseudo) Symm. Elem...          B Check
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          3 Note
              C10 H9 N2

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: Boughzala & Fernandes, preparation of the polynitrile anions: Ktcnoet and K~2~tcpd; Setifi Z. & Setifi F., synthesis of the title compounds; Nummelin & Valkonen , data collection and processing; Glidewell, structure solution & refinement, and writing the paper.


   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: COLLECT (Bruker, 2008) for (I); APEX2 (Bruker, 2009 for (II). Cell refinement: DENZO-SMN (Otwinowski & Minor, 1997) for (I); APEX2 and SAINT (Bruker, 2009) for (II). Data reduction: DENZO-SMN (Otwinowski & Minor, 1997) for (I); SAINT (Bruker, 2009) for (II). Program(s) used to solve structure: SIR2011 (Burla et al., 2012) for (I); SHELXS97 (Sheldrick, 2008) for (II). For both compounds, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

(I) 2,2'-Bipyridin-1-ium 1,1,3,3-tetracyano-2-ethoxyprop-2-en-1-ide top

Crystal data top

C₁₀H₉N₂⁺·C₉H₅N₄O⁻	Z = 2
M_r = 342.36	F(000) = 356
Triclinic, P1	D_x = 1.339 Mg m⁻³
a = 7.2514 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6647 (2) Å	Cell parameters from 4152 reflections
c = 11.5619 (2) Å	θ = 2.9–28.3°
α = 100.020 (1)°	µ = 0.09 mm⁻¹
β = 104.372 (1)°	T = 123 K
γ = 92.590 (1)°	Plate, pale orange
V = 849.27 (3) Å³	0.40 × 0.35 × 0.13 mm

Data collection top

Bruker APEXII CCD diffractometer	4152 independent reflections
Radiation source: fine-focus sealed tube	3447 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
φ & ω scans	θ_max = 28.3°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→9
T_min = 0.870, T_max = 0.988	k = −11→14
6234 measured reflections	l = −15→15

Refinement top

Refinement on F²	3 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.103	w = 1/[σ²(F_o²) + (0.0362P)² + 0.2911P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
4152 reflections	Δρ_max = 0.25 e Å⁻³
259 parameters	Δρ_min = −0.20 e Å⁻³

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N11	0.21857 (15)	0.52707 (9)	0.43771 (10)	0.0285 (2)
H11	0.304 (2)	0.5526 (14)	0.5105 (14)	0.034*
C12	0.13048 (16)	0.40769 (10)	0.41532 (11)	0.0250 (2)
C13	−0.00916 (18)	0.36846 (12)	0.30713 (11)	0.0300 (3)
H13	−0.0760	0.2858	0.2891	0.036*
C14	−0.0511 (2)	0.45071 (13)	0.22510 (12)	0.0354 (3)
H14	−0.1463	0.4240	0.1505	0.042*
C15	0.0455 (2)	0.57160 (13)	0.25183 (13)	0.0370 (3)
H15	0.0191	0.6278	0.1956	0.044*
C16	0.18018 (19)	0.60851 (12)	0.36102 (13)	0.0347 (3)
H16	0.2459	0.6917	0.3820	0.042*
N21	0.33192 (15)	0.39123 (10)	0.60741 (9)	0.0298 (2)
C22	0.19143 (16)	0.33195 (11)	0.51119 (10)	0.0248 (2)
C23	0.10772 (18)	0.20973 (12)	0.50218 (12)	0.0316 (3)
H23	0.0098	0.1704	0.4324	0.038*
C24	0.1711 (2)	0.14670 (12)	0.59796 (13)	0.0358 (3)
H24	0.1167	0.0631	0.5949	0.043*
C25	0.31365 (19)	0.20658 (13)	0.69753 (12)	0.0336 (3)
H25	0.3585	0.1656	0.7645	0.040*
C26	0.39027 (18)	0.32811 (13)	0.69780 (12)	0.0334 (3)
H26	0.4898	0.3686	0.7662	0.040*
C31	0.63575 (17)	0.92545 (11)	0.75796 (11)	0.0258 (2)
C32	0.66992 (16)	0.94146 (11)	0.88432 (11)	0.0243 (2)
C33	0.73776 (16)	1.05351 (11)	0.97022 (10)	0.0252 (2)
C311	0.52991 (19)	0.81335 (12)	0.68277 (12)	0.0327 (3)
N311	0.4472 (2)	0.72078 (12)	0.62292 (12)	0.0525 (4)
C312	0.69653 (17)	1.01940 (11)	0.69840 (11)	0.0278 (3)
N312	0.74430 (19)	1.09353 (11)	0.64791 (11)	0.0396 (3)
C331	0.78777 (17)	1.04922 (11)	1.09671 (11)	0.0281 (3)
N331	0.83067 (17)	1.05186 (11)	1.19987 (10)	0.0365 (3)
C332	0.74824 (17)	1.17768 (11)	0.94263 (11)	0.0277 (2)
N332	0.75833 (18)	1.28170 (10)	0.92815 (10)	0.0366 (3)
O321	0.62639 (12)	0.83982 (8)	0.93268 (8)	0.0279 (2)	0.634 (9)
C321	0.7550 (4)	0.7422 (3)	0.9381 (5)	0.0381 (9)	0.634 (9)
H32A	0.8632	0.7663	1.0117	0.046*	0.634 (9)
H32B	0.8069	0.7308	0.8658	0.046*	0.634 (9)
C322	0.6481 (8)	0.6213 (3)	0.9417 (6)	0.0430 (11)	0.634 (9)
H32C	0.7343	0.5530	0.9458	0.064*	0.634 (9)
H32D	0.5422	0.5977	0.8681	0.064*	0.634 (9)
H32E	0.5974	0.6334	1.0135	0.064*	0.634 (9)
O341	0.62639 (12)	0.83982 (8)	0.93268 (8)	0.0279 (2)	0.366 (9)
C341	0.6787 (17)	0.7134 (5)	0.8864 (6)	0.051 (2)	0.366 (9)
H34A	0.8019	0.7218	0.8647	0.061*	0.366 (9)
H34B	0.5796	0.6712	0.8125	0.061*	0.366 (9)
C342	0.6957 (17)	0.6360 (6)	0.9825 (6)	0.0423 (18)	0.366 (9)
H42C	0.7350	0.5519	0.9541	0.063*	0.366 (9)
H42D	0.5718	0.6252	1.0010	0.063*	0.366 (9)
H42E	0.7914	0.6796	1.0560	0.063*	0.366 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N11	0.0302 (5)	0.0213 (5)	0.0365 (6)	−0.0010 (4)	0.0157 (4)	0.0026 (4)
C12	0.0269 (6)	0.0197 (5)	0.0310 (6)	0.0016 (4)	0.0148 (5)	0.0016 (4)
C13	0.0346 (6)	0.0245 (6)	0.0316 (6)	0.0005 (5)	0.0123 (5)	0.0021 (5)
C14	0.0414 (7)	0.0367 (7)	0.0310 (6)	0.0075 (6)	0.0142 (6)	0.0065 (5)
C15	0.0456 (8)	0.0347 (7)	0.0422 (7)	0.0120 (6)	0.0257 (6)	0.0161 (6)
C16	0.0394 (7)	0.0243 (6)	0.0491 (8)	0.0029 (5)	0.0261 (6)	0.0097 (5)
N21	0.0296 (5)	0.0285 (5)	0.0301 (5)	−0.0028 (4)	0.0097 (4)	0.0011 (4)
C22	0.0254 (5)	0.0216 (5)	0.0283 (6)	0.0006 (4)	0.0113 (4)	0.0012 (4)
C23	0.0338 (6)	0.0232 (6)	0.0342 (6)	−0.0026 (5)	0.0047 (5)	0.0035 (5)
C24	0.0398 (7)	0.0245 (6)	0.0419 (7)	−0.0003 (5)	0.0076 (6)	0.0084 (5)
C25	0.0326 (6)	0.0342 (7)	0.0361 (7)	0.0068 (5)	0.0092 (5)	0.0107 (5)
C26	0.0293 (6)	0.0373 (7)	0.0313 (6)	−0.0007 (5)	0.0066 (5)	0.0031 (5)
C31	0.0275 (6)	0.0206 (5)	0.0310 (6)	−0.0001 (4)	0.0110 (5)	0.0049 (4)
C32	0.0212 (5)	0.0218 (5)	0.0332 (6)	0.0027 (4)	0.0102 (4)	0.0092 (4)
C33	0.0241 (5)	0.0246 (6)	0.0280 (6)	0.0020 (4)	0.0067 (4)	0.0082 (4)
C311	0.0382 (7)	0.0266 (6)	0.0371 (7)	−0.0017 (5)	0.0197 (5)	0.0027 (5)
N311	0.0676 (9)	0.0374 (7)	0.0510 (8)	−0.0208 (6)	0.0312 (7)	−0.0117 (6)
C312	0.0327 (6)	0.0219 (5)	0.0297 (6)	0.0019 (4)	0.0116 (5)	0.0020 (4)
N312	0.0552 (7)	0.0269 (5)	0.0423 (6)	0.0002 (5)	0.0233 (6)	0.0075 (5)
C331	0.0272 (6)	0.0240 (6)	0.0334 (7)	−0.0001 (4)	0.0071 (5)	0.0082 (5)
N331	0.0447 (7)	0.0315 (6)	0.0314 (6)	−0.0005 (5)	0.0047 (5)	0.0095 (4)
C332	0.0308 (6)	0.0257 (6)	0.0253 (6)	0.0025 (4)	0.0057 (5)	0.0042 (4)
N332	0.0522 (7)	0.0265 (6)	0.0300 (6)	0.0033 (5)	0.0082 (5)	0.0063 (4)
O321	0.0309 (4)	0.0215 (4)	0.0357 (5)	0.0025 (3)	0.0145 (4)	0.0092 (3)
C321	0.0313 (13)	0.0412 (15)	0.055 (2)	0.0185 (11)	0.0194 (12)	0.0291 (14)
C322	0.061 (3)	0.0208 (13)	0.054 (3)	0.0070 (12)	0.027 (2)	0.0080 (15)
O341	0.0309 (4)	0.0215 (4)	0.0357 (5)	0.0025 (3)	0.0145 (4)	0.0092 (3)
C341	0.090 (6)	0.037 (3)	0.039 (3)	0.033 (3)	0.029 (3)	0.019 (2)
C342	0.061 (5)	0.026 (3)	0.043 (4)	0.010 (2)	0.018 (3)	0.007 (2)

Geometric parameters (Å, º) top

N11—C16	1.3361 (17)	C32—C33	1.3956 (16)
N11—C12	1.3512 (14)	C31—C311	1.4136 (16)
N11—H11	0.901 (16)	C31—C312	1.4224 (16)
C12—C13	1.3842 (17)	C33—C331	1.4261 (17)
C12—C22	1.4755 (17)	C33—C332	1.4181 (16)
C13—C14	1.3900 (18)	C32—O321	1.3618 (13)
C13—H13	0.9500	O321—C321	1.428 (2)
C14—C15	1.3860 (19)	C311—N311	1.1471 (17)
C14—H14	0.9500	C312—N312	1.1498 (16)
C15—C16	1.372 (2)	C331—N331	1.1504 (16)
C15—H15	0.9500	C332—N332	1.1522 (16)
C16—H16	0.9500	C321—C322	1.487 (3)
N21—C26	1.3325 (17)	C321—H32A	0.9900
N21—C22	1.3451 (15)	C321—H32B	0.9900
C22—C23	1.3886 (16)	C322—H32C	0.9800
C23—C24	1.3870 (18)	C322—H32D	0.9800
C23—H23	0.9500	C322—H32E	0.9800
C24—C25	1.3767 (19)	C341—C342	1.480 (4)
C24—H24	0.9500	C341—H34A	0.9900
C25—C26	1.3861 (18)	C341—H34B	0.9900
C25—H25	0.9500	C342—H42C	0.9800
C26—H26	0.9500	C342—H42D	0.9800
C31—C32	1.3982 (17)	C342—H42E	0.9800

C16—N11—C12	123.83 (12)	C32—C31—C312	123.31 (10)
C16—N11—H11	119.5 (10)	C311—C31—C312	116.80 (11)
C12—N11—H11	116.6 (10)	N311—C311—C31	178.44 (17)
N11—C12—C13	117.84 (11)	N312—C312—C31	178.53 (13)
N11—C12—C22	116.02 (11)	N331—C331—C33	176.77 (13)
C13—C12—C22	126.13 (10)	N332—C332—C33	175.54 (13)
C12—C13—C14	119.62 (12)	C32—C33—C331	119.94 (10)
C12—C13—H13	120.2	C32—C33—C332	124.72 (11)
C14—C13—H13	120.2	C331—C33—C332	115.15 (10)
C15—C14—C13	120.18 (13)	C31—C32—C33	127.46 (10)
C15—C14—H14	119.9	O321—C32—C31	118.45 (10)
C13—C14—H14	119.9	O321—C32—C33	114.02 (10)
C16—C15—C14	118.72 (12)	C32—O321—C321	117.18 (14)
C16—C15—H15	120.6	O321—C321—C322	108.2 (3)
C14—C15—H15	120.6	O321—C321—H32A	110.1
N11—C16—C15	119.78 (12)	C322—C321—H32A	110.1
N11—C16—H16	120.1	O321—C321—H32B	110.1
C15—C16—H16	120.1	C322—C321—H32B	110.1
C26—N21—C22	117.27 (11)	H32A—C321—H32B	108.4
N21—C22—C23	123.22 (11)	C321—C322—H32C	109.5
N21—C22—C12	114.70 (10)	C321—C322—H32D	109.5
C23—C22—C12	122.08 (11)	H32C—C322—H32D	109.5
C24—C23—C22	118.13 (12)	C321—C322—H32E	109.5
C24—C23—H23	120.9	H32C—C322—H32E	109.5
C22—C23—H23	120.9	H32D—C322—H32E	109.5
C25—C24—C23	119.32 (12)	C342—C341—H34A	110.0
C25—C24—H24	120.3	C342—C341—H34B	110.0
C23—C24—H24	120.3	H34A—C341—H34B	108.4
C24—C25—C26	118.46 (12)	C341—C342—H42C	109.5
C24—C25—H25	120.8	C341—C342—H42D	109.5
C26—C25—H25	120.8	H42C—C342—H42D	109.5
N21—C26—C25	123.59 (12)	C341—C342—H42E	109.5
N21—C26—H26	118.2	H42C—C342—H42E	109.5
C25—C26—H26	118.2	H42D—C342—H42E	109.5
C32—C31—C311	119.84 (11)

C16—N11—C12—C13	−0.79 (17)	C22—C23—C24—C25	−0.2 (2)
C16—N11—C12—C22	−179.72 (10)	C23—C24—C25—C26	−0.6 (2)
N11—C12—C13—C14	1.28 (17)	C22—N21—C26—C25	−0.31 (18)
C22—C12—C13—C14	−179.92 (11)	C24—C25—C26—N21	0.9 (2)
C12—C13—C14—C15	−0.39 (19)	C311—C31—C32—O321	10.27 (17)
C13—C14—C15—C16	−1.02 (19)	C312—C31—C32—O321	−172.13 (11)
C12—N11—C16—C15	−0.64 (18)	O321—C32—C33—C331	11.01 (16)
C14—C15—C16—N11	1.53 (19)	O321—C32—C33—C332	−163.73 (11)
C26—N21—C22—C23	−0.53 (17)	C31—C32—C33—C331	−171.92 (11)
C26—N21—C22—C12	178.83 (10)	C31—C32—C33—C332	13.3 (2)
N11—C12—C22—N21	−1.88 (15)	C33—C32—C31—C311	−166.68 (12)
C13—C12—C22—N21	179.30 (11)	C33—C32—C31—C312	10.92 (19)
N11—C12—C22—C23	177.49 (11)	C31—C32—O321—C321	76.5 (3)
C13—C12—C22—C23	−1.34 (18)	C33—C32—O321—C321	−106.2 (3)
N21—C22—C23—C24	0.76 (19)	C32—O321—C321—C322	−156.1 (4)
C12—C22—C23—C24	−178.54 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···N21	0.901 (15)	2.202 (15)	2.6306 (15)	108.5 (12)
N11—H11···N311	0.901 (15)	2.082 (15)	2.8268 (17)	139.2 (13)
C13—H13···N331ⁱ	0.95	2.52	3.4294 (18)	160
C16—H16···N312ⁱⁱ	0.95	2.38	3.2238 (18)	148

Symmetry codes: (i) x−1, y−1, z−1; (ii) −x+1, −y+2, −z+1.

(II) Bis(2,2'-bipyridin-1-ium) 1,1,3,3-tetracyano-2-(dicyanomethylene)propane-1,3-diide top