Multiple N—H⋯NC, C—H⋯NC and nitrile⋯π inter­actions in 4,4′-bi­pyridine-1,1′-diium bis­(1,1,3,3-tetra­cyano-2-eth­oxy­propenide): structure determination and DFT calculations of anion⋯π cation inter­action energies

Setifi, F.; Geiger, D.K.; Abdul Razak, I.; Setifi, Z.

doi:10.1107/S2053229615012437

Multiple N—HNC, C—HNC and nitrileπ interactions in 4,4′-bipyridine-1,1′-diium bis(1,1,3,3-tetracyano-2-ethoxypropenide): structure determination and DFT calculations of anionπ cation interaction energies

F. Setifi, D. K. Geiger, I. Abdul Razak and Z. Setifi

Polynitrile anions are important in both coordination chemistry and molecular materials chemistry, and are interesting for their extensive electronic delocalization. The title compound crystallizes with two symmetry-independent half 4,4′-bipyridine-1,1′-diium (bpyH₂²⁺) cations and two symmetry-independent 1,1,3,3-tetracyano-2-ethoxypropenide (tcnoet⁻) anions in the asymmetric unit. One of the bpyH₂²⁺ ions is located on a crystallographic twofold rotation axis (canted pyridine rings) and the other is located on a crystallographic inversion center (coplanar pyridine rings). The ethyl group of one of the tcnoet⁻ anions is disordered over two sites with equal populations. The extended structure exhibits two separate N—H

NC hydrogen-bonding motifs, which result in a sheet structure parallel to (010), and weak C—H

NC hydrogen bonds form joined rings. Two types of multicenter CN

π interactions are observed between the bpyH₂²⁺ rings and tcnoet⁻ anions. An additonal CN

π interaction between adjacent tcnoet⁻ anions is observed. Using density functional theory, the calculated attractive energy between cation and anion pairs in the tcnoet⁻

π(bipyridinediium) interactions were found to be 557 and 612 kJ mol⁻¹ for coplanar and canted bpyH₂²⁺ cations, respectively.

Keywords: nitrile

π interaction; nitrile hydrogen bonding; anion

π interaction; interaction energies; crystal structure; DFT calculations; polynitrile anions; charge delocalization; 1,1,3,3-tetracyano-2-ethoxypropenide; 4,4′-bipyridine-1,1′-diium.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615012437/ly3016sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229615012437/ly3016Isup2.hkl Contains datablock I
	MDL mol file https://doi.org/10.1107/S2053229615012437/ly3016Isup4.mol Supplementary material

CCDC reference: 1409211

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

4,4'-Bipyridine-1,1'-diium bis(1,1,3,3-tetracyano-2-ethoxypropenide) top

Crystal data top

C₁₀H₁₀N₂²⁺·2C₉H₅N₄O⁻	F(000) = 2192
M_r = 528.54	D_x = 1.316 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 35.847 (3) Å	Cell parameters from 9990 reflections
b = 7.3242 (5) Å	θ = 2.6–24.5°
c = 22.995 (2) Å	µ = 0.09 mm⁻¹
β = 117.882 (3)°	T = 294 K
V = 5336.5 (7) Å³	Block, orange
Z = 8	0.46 × 0.35 × 0.13 mm

Data collection top

Bruker APEXII CCD diffractometer	5675 independent reflections
Radiation source: fine focus sealed tube	4345 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
φ & ω scans	θ_max = 26.7°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −45→45
T_min = 0.96, T_max = 0.99	k = −9→9
43525 measured reflections	l = −29→29

Refinement top

Refinement on F²	6 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.118	w = 1/[σ²(F_o²) + (0.0581P)² + 2.1115P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
5675 reflections	Δρ_max = 0.29 e Å⁻³
390 parameters	Δρ_min = −0.29 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)
N1	0.39236 (3)	0.26112 (18)	0.14620 (6)	0.0479 (3)
H1N	0.3644 (6)	0.262 (3)	0.1202 (8)	0.072 (5)*
C1	0.47684 (3)	0.26421 (18)	0.22777 (6)	0.0350 (3)
C2	0.44919 (4)	0.2021 (2)	0.25006 (6)	0.0432 (3)
H2	0.4594	0.1622	0.2932	0.052*
C3	0.40668 (4)	0.2003 (2)	0.20775 (7)	0.0489 (3)
H3	0.3879	0.1569	0.2219	0.059*
C4	0.41790 (4)	0.3222 (2)	0.12341 (7)	0.0504 (4)
H4	0.4068	0.3633	0.0802	0.06*
C5	0.46072 (4)	0.3247 (2)	0.16351 (6)	0.0438 (3)
H5	0.4787	0.3666	0.1476	0.053*
C12	0.23510 (4)	0.1210 (2)	0.11054 (6)	0.0408 (3)
C14	0.19944 (4)	0.1468 (2)	0.04822 (7)	0.0479 (3)
N14	0.17222 (4)	0.1710 (3)	−0.00318 (6)	0.0723 (5)
C13	0.27414 (4)	0.1754 (2)	0.11506 (6)	0.0473 (3)
N13	0.30549 (4)	0.2211 (2)	0.11787 (7)	0.0714 (4)
C15	0.26439 (4)	0.0254 (2)	0.22702 (6)	0.0421 (3)
C16	0.30440 (4)	−0.0233 (2)	0.23446 (6)	0.0465 (3)
N16	0.33704 (4)	−0.0641 (2)	0.24128 (7)	0.0714 (4)
C17	0.26144 (5)	0.0367 (2)	0.28630 (8)	0.0581 (4)
N17	0.26052 (6)	0.0491 (3)	0.33501 (8)	0.0944 (6)
C11	0.23075 (4)	0.06977 (18)	0.16553 (6)	0.0403 (3)
O1	0.19095 (3)	0.07276 (15)	0.15625 (5)	0.0546 (3)
C18	0.17319 (11)	−0.1040 (5)	0.1640 (2)	0.0632 (9)	0.5
H18A	0.1643	−0.1775	0.1247	0.076*	0.5
H18B	0.1945	−0.1713	0.201	0.076*	0.5
C19	0.1382 (3)	−0.0669 (12)	0.1750 (5)	0.100 (3)	0.5
H19A	0.1158	−0.0142	0.136	0.15*	0.5
H19B	0.1464	0.0171	0.211	0.15*	0.5
H19C	0.1285	−0.1785	0.1853	0.15*	0.5
C98	0.17832 (8)	−0.0259 (5)	0.20030 (14)	0.0437 (6)	0.5
H98A	0.1746	0.0587	0.2296	0.052*	0.5
H98B	0.1997	−0.1147	0.2266	0.052*	0.5
C99	0.1376 (2)	−0.1192 (11)	0.1565 (3)	0.079 (2)	0.5
H99A	0.1169	−0.0297	0.1306	0.118*	0.5
H99B	0.1279	−0.1856	0.1828	0.118*	0.5
H99C	0.1419	−0.2023	0.1278	0.118*	0.5
N2	0.35863 (4)	0.2175 (2)	0.59825 (7)	0.0624 (4)
H2N	0.3878 (7)	0.207 (3)	0.6231 (9)	0.090 (6)*
C6	0.27328 (4)	0.24283 (19)	0.52094 (6)	0.0395 (3)
C7	0.29878 (5)	0.1636 (3)	0.49753 (8)	0.0623 (4)
H7	0.2869	0.1178	0.4549	0.075*
C8	0.34157 (5)	0.1528 (3)	0.53748 (10)	0.0730 (5)
H8	0.3587	0.0998	0.5217	0.088*
C9	0.33554 (5)	0.2927 (3)	0.62248 (8)	0.0637 (4)
H9	0.3484	0.3361	0.6655	0.076*
C10	0.29267 (4)	0.3074 (3)	0.58464 (7)	0.0560 (4)
H10	0.2766	0.3613	0.6021	0.067*
C24	0.51345 (4)	0.24485 (19)	0.63901 (6)	0.0406 (3)
C25	0.54863 (4)	0.2921 (2)	0.69981 (6)	0.0478 (3)
N25	0.57600 (4)	0.3322 (3)	0.74944 (6)	0.0709 (4)
C26	0.47656 (4)	0.1872 (2)	0.64116 (6)	0.0443 (3)
N26	0.44643 (4)	0.1377 (2)	0.64208 (6)	0.0604 (4)
C21	0.47761 (4)	0.28746 (19)	0.51818 (6)	0.0406 (3)
C23	0.43870 (4)	0.3447 (2)	0.51339 (6)	0.0470 (3)
N23	0.40708 (4)	0.3916 (2)	0.50924 (7)	0.0699 (4)
C22	0.47969 (4)	0.2679 (2)	0.45847 (7)	0.0496 (3)
N22	0.47996 (5)	0.2512 (3)	0.40943 (7)	0.0768 (5)
C20	0.51365 (4)	0.26385 (18)	0.57812 (6)	0.0383 (3)
O2	0.54940 (3)	0.26573 (15)	0.57332 (5)	0.0499 (3)
C27	0.58454 (4)	0.1482 (2)	0.61410 (8)	0.0545 (4)
H27A	0.5744	0.0354	0.6238	0.065*
H27B	0.6029	0.2085	0.6552	0.065*
C28	0.60777 (5)	0.1100 (3)	0.57584 (10)	0.0727 (5)
H28A	0.5894	0.0476	0.5358	0.109*
H28B	0.6319	0.0349	0.6016	0.109*
H28C	0.6169	0.223	0.5655	0.109*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0239 (5)	0.0668 (8)	0.0438 (6)	−0.0012 (5)	0.0080 (5)	−0.0009 (5)
C1	0.0259 (6)	0.0464 (7)	0.0302 (6)	0.0005 (5)	0.0111 (5)	−0.0023 (5)
C2	0.0333 (6)	0.0650 (9)	0.0321 (6)	−0.0040 (6)	0.0159 (5)	−0.0003 (6)
C3	0.0325 (6)	0.0719 (10)	0.0449 (7)	−0.0072 (6)	0.0203 (6)	−0.0042 (7)
C4	0.0340 (7)	0.0707 (10)	0.0362 (7)	0.0021 (6)	0.0079 (5)	0.0111 (6)
C5	0.0304 (6)	0.0642 (9)	0.0351 (6)	−0.0009 (6)	0.0140 (5)	0.0078 (6)
C12	0.0265 (6)	0.0544 (8)	0.0383 (6)	0.0005 (5)	0.0124 (5)	0.0048 (6)
C14	0.0315 (6)	0.0670 (9)	0.0427 (7)	−0.0015 (6)	0.0151 (6)	0.0089 (7)
N14	0.0364 (7)	0.1194 (13)	0.0484 (7)	−0.0038 (7)	0.0091 (6)	0.0216 (8)
C13	0.0318 (6)	0.0691 (9)	0.0373 (7)	0.0020 (6)	0.0131 (5)	0.0103 (6)
N13	0.0331 (6)	0.1163 (13)	0.0606 (8)	−0.0024 (7)	0.0184 (6)	0.0260 (8)
C15	0.0378 (6)	0.0513 (8)	0.0391 (7)	0.0044 (6)	0.0195 (5)	0.0053 (6)
C16	0.0395 (7)	0.0617 (9)	0.0323 (6)	0.0062 (6)	0.0118 (5)	0.0057 (6)
N16	0.0417 (7)	0.1111 (13)	0.0576 (8)	0.0244 (7)	0.0200 (6)	0.0210 (8)
C17	0.0637 (9)	0.0666 (10)	0.0532 (9)	0.0179 (8)	0.0351 (8)	0.0177 (8)
N17	0.1268 (15)	0.1157 (15)	0.0693 (10)	0.0426 (12)	0.0697 (11)	0.0303 (10)
C11	0.0307 (6)	0.0450 (7)	0.0460 (7)	0.0033 (5)	0.0186 (5)	0.0062 (6)
O1	0.0348 (5)	0.0708 (7)	0.0639 (6)	0.0117 (4)	0.0277 (4)	0.0261 (5)
C18	0.0473 (19)	0.058 (2)	0.085 (3)	−0.0066 (15)	0.0315 (18)	0.0069 (19)
C19	0.082 (4)	0.082 (5)	0.175 (8)	0.003 (3)	0.093 (5)	0.040 (5)
C98	0.0398 (15)	0.0569 (18)	0.0378 (14)	−0.0043 (12)	0.0210 (12)	0.0020 (13)
C99	0.050 (3)	0.076 (4)	0.074 (3)	−0.011 (2)	−0.001 (2)	0.013 (3)
N2	0.0287 (6)	0.0805 (10)	0.0650 (9)	0.0014 (6)	0.0110 (6)	0.0215 (7)
C6	0.0299 (6)	0.0512 (8)	0.0362 (6)	0.0022 (5)	0.0144 (5)	0.0082 (5)
C7	0.0387 (7)	0.0938 (13)	0.0547 (9)	0.0079 (8)	0.0220 (7)	−0.0074 (8)
C8	0.0393 (8)	0.1022 (15)	0.0815 (12)	0.0133 (9)	0.0317 (9)	0.0050 (11)
C9	0.0401 (8)	0.0924 (13)	0.0443 (8)	−0.0048 (8)	0.0078 (7)	0.0055 (8)
C10	0.0383 (7)	0.0852 (11)	0.0404 (7)	0.0014 (7)	0.0149 (6)	−0.0018 (7)
C24	0.0313 (6)	0.0554 (8)	0.0331 (6)	0.0028 (5)	0.0132 (5)	0.0033 (5)
C25	0.0391 (7)	0.0673 (9)	0.0354 (7)	0.0071 (6)	0.0162 (6)	0.0039 (6)
N25	0.0464 (7)	0.1130 (13)	0.0402 (7)	0.0030 (8)	0.0092 (6)	−0.0088 (7)
C26	0.0367 (7)	0.0603 (9)	0.0355 (6)	0.0077 (6)	0.0165 (5)	0.0076 (6)
N26	0.0399 (6)	0.0909 (10)	0.0534 (7)	0.0041 (6)	0.0242 (6)	0.0138 (7)
C21	0.0358 (6)	0.0541 (8)	0.0317 (6)	−0.0001 (5)	0.0157 (5)	−0.0010 (5)
C23	0.0412 (7)	0.0627 (9)	0.0315 (6)	0.0058 (6)	0.0124 (5)	0.0022 (6)
N23	0.0491 (8)	0.0993 (12)	0.0584 (8)	0.0232 (8)	0.0227 (6)	0.0073 (8)
C22	0.0424 (7)	0.0677 (10)	0.0377 (7)	−0.0037 (6)	0.0178 (6)	−0.0027 (6)
N22	0.0760 (10)	0.1193 (14)	0.0429 (7)	−0.0125 (9)	0.0343 (7)	−0.0109 (8)
C20	0.0330 (6)	0.0452 (7)	0.0371 (6)	−0.0008 (5)	0.0166 (5)	−0.0002 (5)
O2	0.0327 (5)	0.0726 (7)	0.0466 (5)	0.0037 (4)	0.0203 (4)	0.0112 (5)
C27	0.0390 (7)	0.0633 (10)	0.0614 (9)	0.0076 (7)	0.0236 (7)	0.0068 (7)
C28	0.0601 (10)	0.0791 (12)	0.0927 (13)	0.0039 (9)	0.0474 (10)	−0.0107 (10)

Geometric parameters (Å, º) top

N1—C4	1.3273 (18)	C99—H99A	0.96
N1—C3	1.3363 (18)	C99—H99B	0.96
N1—H1N	0.896 (18)	C99—H99C	0.96
C1—C5	1.3837 (17)	N2—C9	1.315 (2)
C1—C2	1.3886 (17)	N2—C8	1.324 (2)
C1—C1ⁱ	1.488 (2)	N2—H2N	0.93 (2)
C2—C3	1.3720 (18)	C6—C10	1.3786 (19)
C2—H2	0.93	C6—C7	1.387 (2)
C3—H3	0.93	C6—C6ⁱⁱ	1.490 (2)
C4—C5	1.3722 (17)	C7—C8	1.373 (2)
C4—H4	0.93	C7—H7	0.93
C5—H5	0.93	C8—H8	0.93
C12—C11	1.3959 (18)	C9—C10	1.371 (2)
C12—C13	1.4113 (17)	C9—H9	0.93
C12—C14	1.4179 (17)	C10—H10	0.93
C14—N14	1.1409 (17)	C24—C20	1.4103 (17)
C13—N13	1.1452 (18)	C24—C26	1.4112 (18)
C15—C11	1.4015 (18)	C24—C25	1.4199 (18)
C15—C16	1.4087 (18)	C25—N25	1.1417 (18)
C15—C17	1.4181 (19)	C26—N26	1.1489 (17)
C16—N16	1.1451 (17)	C21—C20	1.3903 (17)
C17—N17	1.140 (2)	C21—C23	1.4104 (18)
C11—O1	1.3403 (14)	C21—C22	1.4167 (18)
O1—C98	1.477 (3)	C23—N23	1.1449 (18)
O1—C18	1.490 (3)	C22—N22	1.1391 (18)
C18—C19	1.417 (8)	C20—O2	1.3369 (15)
C18—H18A	0.97	O2—C27	1.4499 (17)
C18—H18B	0.97	C27—C28	1.494 (2)
C19—H19A	0.96	C27—H27A	0.97
C19—H19B	0.96	C27—H27B	0.97
C19—H19C	0.96	C28—H28A	0.96
C98—C99	1.496 (7)	C28—H28B	0.96
C98—H98A	0.97	C28—H28C	0.96
C98—H98B	0.97

N26ⁱⁱⁱ···Cg(N1)	3.1950 (15)	N13^v···Cg(N2)ⁱⁱ	3.6500 (19)
N25^iv···Cg(N1)ⁱ	3.4155 (17)	C12···N17^vi	3.353 (2)
N14^v···Cg(N2)	3.5788 (19)	C13···N17^vi	3.419 (3)

C4—N1—C3	122.43 (12)	H99A—C99—H99B	109.5
C4—N1—H1N	119.9 (11)	C98—C99—H99C	109.5
C3—N1—H1N	117.7 (11)	H99A—C99—H99C	109.5
C5—C1—C2	119.03 (11)	H99B—C99—H99C	109.5
C5—C1—C1ⁱ	120.56 (13)	C9—N2—C8	121.70 (14)
C2—C1—C1ⁱ	120.40 (13)	C9—N2—H2N	121.5 (12)
C3—C2—C1	119.29 (12)	C8—N2—H2N	116.8 (12)
C3—C2—H2	120.4	C10—C6—C7	117.37 (13)
C1—C2—H2	120.4	C10—C6—C6ⁱⁱ	121.23 (15)
N1—C3—C2	119.81 (12)	C7—C6—C6ⁱⁱ	121.40 (15)
N1—C3—H3	120.1	C8—C7—C6	119.82 (15)
C2—C3—H3	120.1	C8—C7—H7	120.1
N1—C4—C5	120.03 (12)	C6—C7—H7	120.1
N1—C4—H4	120.0	N2—C8—C7	120.40 (16)
C5—C4—H4	120.0	N2—C8—H8	119.8
C4—C5—C1	119.39 (12)	C7—C8—H8	119.8
C4—C5—H5	120.3	N2—C9—C10	120.31 (15)
C1—C5—H5	120.3	N2—C9—H9	119.8
C11—C12—C13	122.43 (11)	C10—C9—H9	119.8
C11—C12—C14	121.43 (11)	C9—C10—C6	120.40 (15)
C13—C12—C14	115.54 (11)	C9—C10—H10	119.8
N14—C14—C12	176.22 (15)	C6—C10—H10	119.8
N13—C13—C12	178.96 (16)	C20—C24—C26	120.28 (11)
C11—C15—C16	121.88 (11)	C20—C24—C25	122.63 (12)
C11—C15—C17	122.72 (12)	C26—C24—C25	116.99 (11)
C16—C15—C17	115.30 (12)	N25—C25—C24	177.71 (16)
N16—C16—C15	179.08 (16)	N26—C26—C24	178.72 (17)
N17—C17—C15	177.4 (2)	C20—C21—C23	122.74 (11)
O1—C11—C12	114.39 (11)	C20—C21—C22	120.17 (12)
O1—C11—C15	120.93 (11)	C23—C21—C22	116.91 (11)
C12—C11—C15	124.63 (11)	N23—C23—C21	179.67 (17)
C11—O1—C98	121.84 (14)	N22—C22—C21	177.74 (16)
C11—O1—C18	116.72 (16)	O2—C20—C21	113.52 (11)
C19—C18—O1	108.6 (4)	O2—C20—C24	122.20 (11)
C19—C18—H18A	110.0	C21—C20—C24	124.25 (11)
O1—C18—H18A	110.0	C20—O2—C27	121.14 (11)
C19—C18—H18B	110.0	O2—C27—C28	106.58 (13)
O1—C18—H18B	110.0	O2—C27—H27A	110.4
H18A—C18—H18B	108.3	C28—C27—H27A	110.4
C18—C19—H19A	109.5	O2—C27—H27B	110.4
C18—C19—H19B	109.5	C28—C27—H27B	110.4
H19A—C19—H19B	109.5	H27A—C27—H27B	108.6
C18—C19—H19C	109.5	C27—C28—H28A	109.5
H19A—C19—H19C	109.5	C27—C28—H28B	109.5
H19B—C19—H19C	109.5	H28A—C28—H28B	109.5
O1—C98—C99	106.1 (4)	C27—C28—H28C	109.5
O1—C98—H98A	110.5	H28A—C28—H28C	109.5
C99—C98—H98A	110.5	H28B—C28—H28C	109.5
O1—C98—H98B	110.5	Cg(N1)—N26ⁱⁱⁱ—C26ⁱⁱⁱ	124.49 (11)
C99—C98—H98B	110.5	Cg(N1)—N25^iv—C25^iv	116.23 (12)
H98A—C98—H98B	108.7	Cg(N2)—N14^v—C14^v	92.98 (13)
C98—C99—H99A	109.5	Cg(N2)—N13^v—C13^v	89.46 (13)
C98—C99—H99B	109.5

C5—C1—C2—C3	0.7 (2)	C11—O1—C98—C99	−135.7 (4)
C1ⁱ—C1—C2—C3	−178.79 (11)	C18—O1—C98—C99	−42.2 (4)
C4—N1—C3—C2	0.9 (2)	C10—C6—C7—C8	−0.3 (3)
C1—C2—C3—N1	−1.2 (2)	C6ⁱⁱ—C6—C7—C8	179.94 (18)
C3—N1—C4—C5	−0.1 (2)	C9—N2—C8—C7	0.3 (3)
N1—C4—C5—C1	−0.4 (2)	C6—C7—C8—N2	0.1 (3)
C2—C1—C5—C4	0.1 (2)	C8—N2—C9—C10	−0.5 (3)
C1ⁱ—C1—C5—C4	179.60 (11)	N2—C9—C10—C6	0.3 (3)
C13—C12—C11—O1	161.87 (14)	C7—C6—C10—C9	0.1 (2)
C14—C12—C11—O1	−8.8 (2)	C6ⁱⁱ—C6—C10—C9	179.86 (17)
C13—C12—C11—C15	−15.5 (2)	C23—C21—C20—O2	−160.23 (13)
C14—C12—C11—C15	173.81 (14)	C22—C21—C20—O2	14.79 (19)
C16—C15—C11—O1	163.81 (13)	C23—C21—C20—C24	18.0 (2)
C17—C15—C11—O1	−20.1 (2)	C22—C21—C20—C24	−166.99 (14)
C16—C15—C11—C12	−19.0 (2)	C26—C24—C20—O2	−160.23 (13)
C17—C15—C11—C12	157.18 (15)	C25—C24—C20—O2	23.6 (2)
C12—C11—O1—C98	161.72 (19)	C26—C24—C20—C21	21.7 (2)
C15—C11—O1—C98	−20.8 (2)	C25—C24—C20—C21	−154.43 (14)
C12—C11—O1—C18	118.8 (2)	C21—C20—O2—C27	−143.64 (13)
C15—C11—O1—C18	−63.7 (3)	C24—C20—O2—C27	38.10 (19)
C11—O1—C18—C19	160.3 (4)	C20—O2—C27—C28	151.24 (13)

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1/2, −y+1/2, −z+1; (iii) x, −y, z−1/2; (iv) x, −y+1, z−1/2; (v) −x+1/2, −y+1/2, −z; (vi) −x+1/2, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N14^v	0.896 (18)	2.429 (17)	3.0498 (17)	126.6 (14)
N1—H1N···N13	0.896 (18)	2.107 (18)	2.8826 (17)	144.2 (15)
C2—H2···N22	0.93	2.5	3.3157 (18)	146
C3—H3···N16	0.93	2.63	3.518 (2)	161
C4—H4···N14^v	0.93	2.55	3.1190 (18)	119
C4—H4···N23^iv	0.93	2.43	3.238 (2)	145
C5—H5···N22ⁱ	0.93	2.54	3.311 (2)	141
C98—H98B···N17	0.97	2.71	3.169 (3)	110
N2—H2N···N26	0.93 (2)	2.00 (2)	2.8803 (18)	156.5 (17)
C7—H7···N17	0.93	2.51	3.429 (2)	169
C9—H9···N25^vii	0.93	2.49	3.175 (2)	130
C10—H10···N17ⁱⁱ	0.93	2.47	3.384 (2)	168
C27—H27B···N16^viii	0.97	2.57	3.2555 (19)	127

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1/2, −y+1/2, −z+1; (iv) x, −y+1, z−1/2; (v) −x+1/2, −y+1/2, −z; (vii) −x+1, y, −z+3/2; (viii) −x+1, −y, −z+1.

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Multiple N—HNC, C—HNC and nitrileπ inter­actions in 4,4′-bi­pyridine-1,1′-diium bis­(1,1,3,3-tetra­cyano-2-eth­oxy­propenide): structure determination and DFT calculations of anionπ cation inter­action energies

Supporting information

Multiple N—HNC, C—HNC and nitrileπ interactions in 4,4′-bipyridine-1,1′-diium bis(1,1,3,3-tetracyano-2-ethoxypropenide): structure determination and DFT calculations of anionπ cation interaction energies