Crystal structure of [tris­(4,4′-bi­pyridine)]­diium bis­(1,1,3,3-tetra­cyano-2-eth­oxy­propenide) trihydrate

Setifi, F.; Valkonen, A.; Setifi, Z.; Nummelin, S.; Touzani, R.; Glidewell, C.

doi:10.1107/S2056989016012160

Crystal structure of [tris(4,4′-bipyridine)]diium bis(1,1,3,3-tetracyano-2-ethoxypropenide) trihydrate

F. Setifi, A. Valkonen, Z. Setifi, S. Nummelin, R. Touzani and C. Glidewell

In the title hydrated salt, which was obtained from the hydrothermal reaction between between potassium 1,1,3,3-tetracyano-2-ethoxypropenide and 4,4′-bipyridine in the presence of iron(II) sulfate heptahydrate, the ionic components are linked into a three-dimensional network by C—H

N hydrogen bonds.

Keywords: crystal structure; hydrothermal synthesis; polynitrile anions; molecular structure; hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989016012160/hb7603sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989016012160/hb7603Isup2.hkl Contains datablock I

CCDC reference: 1496221

checkCIF report

Key indicators

Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.002 Å
H-atom completeness 86%
Disorder in main residue
R factor = 0.049
wR factor = 0.115
Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT430_ALERT_2_A Short Inter D...A Contact  O6A    ..  O6A     ..       1.78 Ang.

Author Response: (Level A alerts). The short O6A...O6A and O6B...O6B contacts involve atom sites with occupancies 0.34(2) and 0.16(2) respectively, so that there is no requirement for both of the close-contact sites in any pair to be occupied concurrently.

 (Level B alerts). The other close contact sites involving atoms
 O5A, O5B or N atoms are all comfortably within hydrogen-bonding
 distances and, had it been possible to locate the H atoms of
 the partial-occupancy water molecules, these contacts would all
 have appeared in the hydrogen-bond Table,

PLAT430_ALERT_2_A Short Inter D...A Contact  O6B    ..  O6B     ..       2.38 Ang.

 (Level B alerts). The other close contact sites involving atoms
 O5A, O5B or N atoms are all comfortably within hydrogen-bonding
 distances and, had it been possible to locate the H atoms of
 the partial-occupancy water molecules, these contacts would all
 have appeared in the hydrogen-bond Table,


Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O5A    ..  O5A     ..       2.74 Ang.

 (Level B alerts). The other close contact sites involving atoms
 O5A, O5B or N atoms are all comfortably within hydrogen-bonding
 distances and, had it been possible to locate the H atoms of
 the partial-occupancy water molecules, these contacts would all
 have appeared in the hydrogen-bond Table,

PLAT430_ALERT_2_B Short Inter D...A Contact  O5A    ..  N412    ..       2.82 Ang.

 (Level B alerts). The other close contact sites involving atoms
 O5A, O5B or N atoms are all comfortably within hydrogen-bonding
 distances and, had it been possible to locate the H atoms of
 the partial-occupancy water molecules, these contacts would all
 have appeared in the hydrogen-bond Table,

PLAT430_ALERT_2_B Short Inter D...A Contact  N432   ..  O6A     ..       2.85 Ang.

 (Level B alerts). The other close contact sites involving atoms
 O5A, O5B or N atoms are all comfortably within hydrogen-bonding
 distances and, had it been possible to locate the H atoms of
 the partial-occupancy water molecules, these contacts would all
 have appeared in the hydrogen-bond Table,

PLAT430_ALERT_2_B Short Inter D...A Contact  O5B    ..  O5B     ..       2.76 Ang.

 (Level B alerts). The other close contact sites involving atoms
 O5A, O5B or N atoms are all comfortably within hydrogen-bonding
 distances and, had it been possible to locate the H atoms of
 the partial-occupancy water molecules, these contacts would all
 have appeared in the hydrogen-bond Table,


Alert level C
PLAT041_ALERT_1_C Calc. and Reported SumFormula    Strings  Differ     Please Check
PLAT043_ALERT_1_C Calculated and Reported Mol. Weight Differ by ..       6.04 Check
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...     Please Check
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C9 H5 N4 O
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      4.794 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         30 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....         13 Note

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C48 H42 N14 O5
            Atom count from the _atom_site data:  C48 H36 N14 O5
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C48 H42 N14 O5
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        192.00    192.00    0.00
           H        168.00    144.00   24.00
           N         56.00     56.00    0.00
           O         20.00     20.00    0.00
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       5.29 Why ?
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C41    --  C412    ..        5.8 s.u.
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C43    --  C431    ..        6.4 s.u.
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C43    --  C432    ..        5.5 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ............ Percentage =          4 Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms (  21.32) in Resd. #          2 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms (  20.34) in Resd. #          3 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms (   0.52) in Resd. #          4 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms (   0.48) in Resd. #          5 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms (   0.34) in Resd. #          6 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms (   0.16) in Resd. #          7 Check
PLAT311_ALERT_2_G Isolated Disordered Oxygen Atom (No H's ?) .....        O5A Check
PLAT311_ALERT_2_G Isolated Disordered Oxygen Atom (No H's ?) .....        O5B Check
PLAT311_ALERT_2_G Isolated Disordered Oxygen Atom (No H's ?) .....        O6A Check
PLAT311_ALERT_2_G Isolated Disordered Oxygen Atom (No H's ?) .....        O6B Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          8 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density          17 Note

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

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  16 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
   8 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.

   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); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); 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).

[Tris(4,4-bipyridine)]diium bis(1,1,3,3-tetracyano-2-ethoxypropenide) trihydrate top

Crystal data top

C₃₀H₂₆N₆²⁺·2C₉H₅N₄O⁻·3H₂O	F(000) = 1872
M_r = 894.95	D_x = 1.299 Mg m⁻³
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 18.1861 (2) Å	Cell parameters from 5197 reflections
b = 7.1187 (1) Å	θ = 2.3–27.5°
c = 35.7070 (4) Å	µ = 0.09 mm⁻¹
β = 100.448 (1)°	T = 123 K
V = 4546.03 (10) Å³	Block, pale yellow
Z = 4	0.45 × 0.38 × 0.31 mm

Data collection top

Bruker–Nonius Kappa CCD with APEXII detector diffractometer	5197 independent reflections
Radiation source: fine focus sealed tube	4559 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
φ and ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −23→23
T_min = 0.907, T_max = 0.973	k = −8→9
35680 measured reflections	l = −42→46

Refinement top

Refinement on F²	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.115	w = 1/[σ²(F_o²) + (0.0362P)² + 5.2868P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
5197 reflections	Δρ_max = 0.32 e Å⁻³
335 parameters	Δρ_min = −0.23 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.34943 (7)	0.62579 (18)	0.59359 (3)	0.0268 (3)
H11	0.3778 (17)	0.621 (4)	0.6196 (11)	0.032*	0.66 (4)
C12	0.34888 (8)	0.7810 (2)	0.57234 (4)	0.0260 (3)
H12	0.3753	0.8893	0.5830	0.031*
C13	0.31054 (7)	0.7862 (2)	0.53523 (4)	0.0234 (3)
H13	0.3109	0.8967	0.5204	0.028*
C14	0.27134 (7)	0.62756 (19)	0.51984 (3)	0.0192 (3)
C15	0.27272 (8)	0.4676 (2)	0.54248 (4)	0.0244 (3)
H15	0.2466	0.3574	0.5327	0.029*
C16	0.31261 (8)	0.4715 (2)	0.57924 (4)	0.0276 (3)
H16	0.3140	0.3625	0.5947	0.033*
N21	0.42091 (7)	0.62202 (17)	0.66569 (4)	0.0269 (3)
H21	0.400 (3)	0.616 (8)	0.641 (2)	0.032*	0.34 (4)
C22	0.49341 (8)	0.5785 (2)	0.67630 (4)	0.0276 (3)
H22	0.5217	0.5488	0.6572	0.033*
C23	0.52856 (8)	0.5754 (2)	0.71399 (4)	0.0256 (3)
H23	0.5802	0.5455	0.7206	0.031*
C24	0.48726 (8)	0.61675 (19)	0.74231 (4)	0.0219 (3)
C25	0.41210 (8)	0.6605 (2)	0.73098 (4)	0.0258 (3)
H25	0.3821	0.6887	0.7494	0.031*
C26	0.38118 (8)	0.6626 (2)	0.69263 (4)	0.0277 (3)
H26	0.3298	0.6940	0.6852	0.033*
N31	0.58874 (8)	0.61811 (19)	0.86102 (3)	0.0331 (3)
C32	0.51622 (9)	0.5772 (2)	0.84948 (4)	0.0327 (3)
H32	0.4872	0.5488	0.8683	0.039*
C33	0.48101 (9)	0.5739 (2)	0.81152 (4)	0.0281 (3)
H33	0.4294	0.5438	0.8049	0.034*
C34	0.52250 (8)	0.61556 (19)	0.78334 (4)	0.0227 (3)
C35	0.59782 (8)	0.6576 (2)	0.79502 (4)	0.0270 (3)
H35	0.6283	0.6867	0.7768	0.032*
C36	0.62787 (9)	0.6565 (2)	0.83360 (4)	0.0313 (3)
H36	0.6795	0.6848	0.8410	0.038*
C41	0.15157 (8)	−0.1715 (2)	0.58797 (4)	0.0272 (3)
C42	0.11579 (7)	−0.3411 (2)	0.57565 (4)	0.0234 (3)
C43	0.11642 (8)	−0.5041 (2)	0.59765 (4)	0.0249 (3)
C411	0.16626 (8)	−0.0335 (2)	0.56164 (4)	0.0297 (3)
N411	0.17940 (8)	0.0773 (2)	0.54035 (4)	0.0382 (3)
C412	0.17576 (9)	−0.1283 (2)	0.62709 (5)	0.0347 (4)
N412	0.19482 (10)	−0.0875 (3)	0.65855 (5)	0.0528 (4)
C431	0.06545 (8)	−0.6532 (2)	0.58565 (4)	0.0262 (3)
N431	0.02403 (7)	−0.77540 (19)	0.57765 (4)	0.0333 (3)
C432	0.16949 (9)	−0.5343 (2)	0.63136 (4)	0.0321 (3)
N432	0.21320 (9)	−0.5619 (3)	0.65832 (4)	0.0496 (4)
O421	0.08005 (6)	−0.35955 (15)	0.53932 (3)	0.0283 (2)
C421	0.02174 (9)	−0.2228 (2)	0.52443 (4)	0.0330 (3)
H41A	0.0143	−0.2200	0.4963	0.040*
H41B	0.0372	−0.0959	0.5341	0.040*
C422	−0.04964 (9)	−0.2764 (3)	0.53674 (5)	0.0427 (4)
H42A	−0.0886	−0.1850	0.5268	0.064*
H42B	−0.0650	−0.4016	0.5269	0.064*
H42C	−0.0421	−0.2778	0.5646	0.064*
O5A	0.2512 (2)	0.9317 (7)	0.73743 (12)	0.0915 (17)	0.522 (6)
O5B	0.28182 (16)	0.9204 (5)	0.76234 (11)	0.0533 (13)	0.478 (6)
O6A	0.7139 (8)	0.743 (4)	0.7296 (2)	0.055 (4)	0.34 (3)
O6B	0.7007 (9)	0.824 (4)	0.7286 (3)	0.031 (4)	0.16 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N11	0.0253 (6)	0.0364 (7)	0.0166 (5)	0.0030 (5)	−0.0018 (5)	0.0009 (5)
C12	0.0241 (7)	0.0309 (8)	0.0210 (6)	−0.0013 (6)	−0.0013 (5)	−0.0028 (6)
C13	0.0248 (6)	0.0246 (7)	0.0199 (6)	−0.0014 (5)	0.0015 (5)	0.0007 (5)
C14	0.0165 (6)	0.0233 (7)	0.0169 (6)	0.0020 (5)	0.0011 (5)	0.0004 (5)
C15	0.0244 (6)	0.0254 (7)	0.0224 (7)	−0.0016 (6)	0.0013 (5)	0.0016 (5)
C16	0.0295 (7)	0.0306 (8)	0.0217 (7)	0.0026 (6)	0.0020 (5)	0.0063 (6)
N21	0.0325 (6)	0.0262 (6)	0.0188 (6)	−0.0020 (5)	−0.0036 (5)	0.0016 (5)
C22	0.0322 (7)	0.0283 (7)	0.0216 (7)	−0.0004 (6)	0.0034 (6)	0.0011 (6)
C23	0.0259 (7)	0.0255 (7)	0.0235 (7)	0.0015 (6)	−0.0002 (5)	0.0007 (5)
C24	0.0269 (7)	0.0174 (6)	0.0197 (6)	−0.0014 (5)	0.0001 (5)	0.0006 (5)
C25	0.0270 (7)	0.0265 (7)	0.0228 (7)	−0.0006 (6)	0.0016 (5)	−0.0024 (5)
C26	0.0260 (7)	0.0280 (8)	0.0259 (7)	−0.0003 (6)	−0.0035 (5)	−0.0002 (6)
N31	0.0437 (8)	0.0285 (7)	0.0227 (6)	0.0020 (6)	−0.0053 (5)	0.0004 (5)
C32	0.0466 (9)	0.0287 (8)	0.0216 (7)	−0.0022 (7)	0.0029 (6)	0.0032 (6)
C33	0.0332 (7)	0.0253 (7)	0.0239 (7)	−0.0026 (6)	0.0003 (6)	0.0014 (6)
C34	0.0295 (7)	0.0174 (6)	0.0193 (6)	0.0035 (5)	−0.0010 (5)	−0.0005 (5)
C35	0.0292 (7)	0.0249 (7)	0.0250 (7)	0.0031 (6)	0.0001 (6)	−0.0028 (5)
C36	0.0324 (8)	0.0294 (8)	0.0280 (7)	0.0037 (6)	−0.0054 (6)	−0.0041 (6)
C41	0.0283 (7)	0.0256 (7)	0.0286 (7)	−0.0013 (6)	0.0074 (6)	−0.0023 (6)
C42	0.0226 (6)	0.0266 (7)	0.0217 (6)	0.0015 (5)	0.0060 (5)	−0.0009 (5)
C43	0.0246 (7)	0.0266 (7)	0.0233 (7)	−0.0006 (6)	0.0038 (5)	0.0012 (5)
C411	0.0284 (7)	0.0245 (7)	0.0379 (8)	−0.0001 (6)	0.0108 (6)	−0.0039 (6)
N411	0.0419 (8)	0.0267 (7)	0.0495 (8)	−0.0033 (6)	0.0181 (7)	0.0013 (6)
C412	0.0343 (8)	0.0332 (9)	0.0375 (9)	−0.0080 (7)	0.0084 (7)	−0.0069 (7)
N412	0.0583 (10)	0.0593 (11)	0.0399 (9)	−0.0190 (8)	0.0065 (7)	−0.0157 (8)
C431	0.0278 (7)	0.0265 (7)	0.0250 (7)	0.0036 (6)	0.0068 (5)	0.0037 (6)
N431	0.0345 (7)	0.0284 (7)	0.0366 (7)	−0.0030 (6)	0.0053 (6)	0.0006 (6)
C432	0.0305 (8)	0.0326 (8)	0.0325 (8)	−0.0031 (6)	0.0036 (6)	0.0064 (6)
N432	0.0429 (8)	0.0560 (10)	0.0432 (9)	−0.0030 (7)	−0.0096 (7)	0.0147 (7)
O421	0.0348 (5)	0.0277 (5)	0.0211 (5)	0.0027 (4)	0.0019 (4)	−0.0006 (4)
C421	0.0368 (8)	0.0334 (8)	0.0263 (7)	0.0047 (7)	−0.0011 (6)	0.0061 (6)
C422	0.0353 (9)	0.0423 (10)	0.0489 (10)	0.0042 (8)	0.0031 (7)	−0.0003 (8)
O5A	0.059 (2)	0.166 (4)	0.054 (3)	0.015 (2)	0.021 (2)	0.037 (2)
O5B	0.0324 (15)	0.082 (2)	0.043 (2)	0.0148 (14)	0.0002 (14)	−0.0208 (16)
O6A	0.058 (4)	0.072 (11)	0.038 (2)	−0.021 (6)	0.015 (2)	−0.009 (4)
O6B	0.047 (5)	0.023 (9)	0.027 (4)	0.002 (5)	0.016 (3)	0.000 (4)

Geometric parameters (Å, º) top

N11—C16	1.339 (2)	C33—C34	1.395 (2)
N11—C12	1.3393 (19)	C33—H33	0.9500
N11—H11	0.98 (4)	C34—C35	1.390 (2)
C12—C13	1.3813 (19)	C35—C36	1.387 (2)
C12—H12	0.9500	C35—H35	0.9500
C13—C14	1.3938 (19)	C36—H36	0.9500
C13—H13	0.9500	C41—C42	1.404 (2)
C14—C15	1.3943 (19)	C41—C411	1.418 (2)
C14—C14ⁱ	1.487 (2)	C41—C412	1.420 (2)
C15—C16	1.3802 (19)	C42—O421	1.3480 (16)
C15—H15	0.9500	C411—N411	1.151 (2)
C16—H16	0.9500	C412—N412	1.151 (2)
N21—C26	1.335 (2)	C42—C43	1.400 (2)
N21—C22	1.3405 (19)	C43—C431	1.423 (2)
N21—H21	0.90 (8)	C43—C432	1.416 (2)
C22—C23	1.3813 (19)	C431—N431	1.152 (2)
C22—H22	0.9500	C432—N432	1.149 (2)
C23—C24	1.396 (2)	O421—C421	1.4662 (18)
C23—H23	0.9500	C421—C422	1.493 (2)
C24—C25	1.3887 (19)	C421—H41A	0.9900
C24—C34	1.4885 (18)	C421—H41B	0.9900
C25—C26	1.3826 (19)	C422—H42A	0.9800
C25—H25	0.9500	C422—H42B	0.9800
C26—H26	0.9500	C422—H42C	0.9800
N31—C36	1.339 (2)	O5A—O5B	0.963 (4)
N31—C32	1.340 (2)	O6A—O6B	0.627 (9)
C32—C33	1.390 (2)	O6A—O6Aⁱⁱ	1.78 (2)
C32—H32	0.9500

C16—N11—C12	120.54 (12)	C32—C33—C34	119.08 (14)
C16—N11—H11	118.5 (16)	C32—C33—H33	120.5
C12—N11—H11	121.0 (17)	C34—C33—H33	120.5
N11—C12—C13	121.05 (14)	C35—C34—C33	117.49 (13)
N11—C12—H12	119.5	C35—C34—C24	121.27 (13)
C13—C12—H12	119.5	C33—C34—C24	121.24 (13)
C12—C13—C14	119.33 (13)	C36—C35—C34	119.10 (14)
C12—C13—H13	120.3	C36—C35—H35	120.5
C14—C13—H13	120.3	C34—C35—H35	120.5
C13—C14—C15	118.63 (11)	N31—C36—C35	124.16 (14)
C13—C14—C14ⁱ	121.13 (8)	N31—C36—H36	117.9
C15—C14—C14ⁱ	120.25 (9)	C35—C36—H36	117.9
C16—C15—C14	119.06 (13)	C42—C41—C411	121.34 (13)
C16—C15—H15	120.5	C42—C41—C412	122.53 (14)
C14—C15—H15	120.5	C411—C41—C412	116.12 (14)
N11—C16—C15	121.39 (13)	O421—C42—C43	114.36 (12)
N11—C16—H16	119.3	O421—C42—C41	120.05 (13)
C15—C16—H16	119.3	C41—C42—C43	125.51 (13)
C26—N21—C22	118.63 (12)	C42—C43—C431	120.70 (13)
C26—N21—H21	123 (3)	C42—C43—C432	122.51 (13)
C22—N21—H21	119 (3)	C431—C43—C432	116.70 (13)
N21—C22—C23	122.47 (14)	N411—C411—C41	178.83 (16)
N21—C22—H22	118.8	N412—C412—C41	177.9 (2)
C23—C22—H22	118.8	N431—C431—C43	176.87 (15)
C22—C23—C24	119.19 (13)	N432—C432—C43	178.5 (2)
C22—C23—H23	120.4	C42—O421—C421	118.36 (11)
C24—C23—H23	120.4	O421—C421—C422	109.51 (13)
C25—C24—C23	117.80 (12)	O421—C421—H41A	109.8
C25—C24—C34	120.90 (12)	C422—C421—H41A	109.8
C23—C24—C34	121.30 (12)	O421—C421—H41B	109.8
C26—C25—C24	119.55 (13)	C422—C421—H41B	109.8
C26—C25—H25	120.2	H41A—C421—H41B	108.2
C24—C25—H25	120.2	C421—C422—H42A	109.5
N21—C26—C25	122.35 (13)	C421—C422—H42B	109.5
N21—C26—H26	118.8	H42A—C422—H42B	109.5
C25—C26—H26	118.8	C421—C422—H42C	109.5
C36—N31—C32	116.31 (13)	H42A—C422—H42C	109.5
N31—C32—C33	123.86 (15)	H42B—C422—H42C	109.5
N31—C32—H32	118.1	O6B—O6A—O6Aⁱⁱ	102 (2)
C33—C32—H32	118.1

C16—N11—C12—C13	0.0 (2)	C25—C24—C34—C35	−150.27 (14)
N11—C12—C13—C14	0.5 (2)	C23—C24—C34—C35	29.3 (2)
C12—C13—C14—C15	−0.6 (2)	C25—C24—C34—C33	29.1 (2)
C12—C13—C14—C14ⁱ	179.35 (14)	C23—C24—C34—C33	−151.33 (14)
C13—C14—C15—C16	0.1 (2)	C33—C34—C35—C36	−0.1 (2)
C14ⁱ—C14—C15—C16	−179.83 (14)	C24—C34—C35—C36	179.35 (13)
C12—N11—C16—C15	−0.5 (2)	C32—N31—C36—C35	0.6 (2)
C14—C15—C16—N11	0.4 (2)	C34—C35—C36—N31	−0.4 (2)
C26—N21—C22—C23	−0.4 (2)	C411—C41—C42—O421	−14.7 (2)
N21—C22—C23—C24	0.8 (2)	C412—C41—C42—O421	165.94 (14)
C22—C23—C24—C25	−0.3 (2)	C411—C41—C42—C43	161.79 (14)
C22—C23—C24—C34	−179.91 (13)	C412—C41—C42—C43	−17.6 (2)
C23—C24—C25—C26	−0.3 (2)	O421—C42—C43—C432	158.96 (13)
C34—C24—C25—C26	179.24 (13)	C41—C42—C43—C432	−17.7 (2)
C22—N21—C26—C25	−0.3 (2)	O421—C42—C43—C431	−17.47 (19)
C24—C25—C26—N21	0.7 (2)	C41—C42—C43—C431	165.87 (14)
C36—N31—C32—C33	−0.3 (2)	C43—C42—O421—C421	127.63 (14)
N31—C32—C33—C34	−0.1 (2)	C41—C42—O421—C421	−55.52 (18)
C32—C33—C34—C35	0.3 (2)	C42—O421—C421—C422	−81.41 (17)
C32—C33—C34—C24	−179.10 (13)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···N21	0.98 (4)	1.69 (4)	2.6655 (18)	175 (3)
N21—H21···N11	0.90 (7)	1.78 (7)	2.6655 (18)	172 (5)
C12—H12···N31ⁱⁱⁱ	0.95	2.57	3.4248 (19)	150
C13—H13···N411^iv	0.95	2.56	3.434 (2)	154
C15—H15···N411	0.95	2.38	3.249 (2)	152
C25—H25···O5B	0.95	2.56	3.355 (4)	141
C35—H35···O6A	0.95	2.53	3.474 (13)	176
C35—H35···O6B	0.95	2.54	3.484 (16)	170
C421—H41A···N431^v	0.99	2.61	3.589 (2)	172

Symmetry codes: (iii) −x+1, y+1/2, −z+3/2; (iv) −x+1/2, y+1, −z+1; (v) −x, −y−1, −z+1.

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Crystal structure of [tris­(4,4′-bi­pyridine)]­diium bis­(1,1,3,3-tetra­cyano-2-eth­oxy­propenide) trihydrate

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structure of [tris(4,4′-bipyridine)]diium bis(1,1,3,3-tetracyano-2-ethoxypropenide) trihydrate