Bis(tetra-n-butyl­ammonium) bis­(5,6-di­cyano­pyrazine-2,3-di­thiol­ato-κ²S,S′)nickelate(II)

In the title salt, (C₁₆H₃₆N)₂[Ni(C₆N₄S₂)₂], the centrosymmetric complex dianion is planar, with an r.m.s. deviation of 0.031 (1) Å. The Ni^II atom, lying on an inversion centre, has an almost undistorted square-planar coordination geometry, with Ni—S bond lengths of 2.1606 (5) and 2.1759 (5) Å.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.103
• Data-to-parameter ratio = 24.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.433 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         45 Report

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600       1090 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          5 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Note

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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

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Computing details

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear (Rigaku/MSC, 2006); data reduction: CrystalClear (Rigaku/MSC, 2006); program(s) used to solve structure: SIR2014 (Burla et al., 2015); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015).

Bis(tetra-n-butylammonium) bis(5,6-dicyanopyrazine-2,3-dithiolato-κ²S,S')nickelate(II)

Crystal data

[Ni(C6N4S2)2]·2C16H36N	F(000) = 498
Mr = 928.05	Dx = 1.249 Mg m^−3
Triclinic, P1	Melting point: 516 K
a = 9.8217 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5369 (15) Å	Cell parameters from 3425 reflections
c = 12.974 (2) Å	θ = 1.7–30.7°
α = 69.438 (4)°	µ = 0.60 mm^−1
β = 88.102 (7)°	T = 123 K
γ = 79.086 (7)°	Block, red
V = 1233.6 (3) Å^3	0.20 × 0.20 × 0.07 mm
Z = 1

Data collection

Rigaku/MSC Mercury CCD diffractometer	4998 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.034
Graphite Monochromator monochromator	θmax = 31.0°, θmin = 2.1°
Detector resolution: 14.7059 pixels mm^-1	h = −11→13
φ & ω scans	k = −14→10
11061 measured reflections	l = −17→17
6629 independent reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0426P)^2] where P = (Fo^2 + 2Fc^2)/3
6629 reflections	(Δ/σ)max < 0.001
272 parameters	Δρmax = 0.95 e Å^−3
0 restraints	Δρmin = −0.53 e Å^−3

Special details

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.

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 > 2sigma(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
Ni1	0.500000	0.000000	0.000000	0.02062 (10)
S1	0.43264 (4)	−0.19178 (5)	0.08875 (4)	0.02579 (12)
S2	0.71462 (4)	−0.09135 (5)	0.05557 (4)	0.02277 (12)
N1	0.56827 (13)	−0.42938 (16)	0.22516 (13)	0.0237 (3)
N2	0.82580 (13)	−0.33856 (16)	0.19614 (13)	0.0232 (3)
N3	0.68291 (15)	−0.75826 (18)	0.41323 (15)	0.0321 (4)
N4	1.02495 (16)	−0.64124 (18)	0.37563 (17)	0.0388 (5)
N5	1.03854 (13)	−0.00072 (15)	0.26233 (12)	0.0195 (3)
C1	0.57891 (16)	−0.30369 (19)	0.15852 (15)	0.0216 (4)
C2	0.71003 (16)	−0.25614 (19)	0.14286 (15)	0.0206 (4)
C3	0.68651 (17)	−0.51067 (19)	0.27881 (16)	0.0232 (4)
C4	0.81279 (16)	−0.46538 (19)	0.26411 (16)	0.0233 (4)
C5	0.67992 (17)	−0.6480 (2)	0.35339 (16)	0.0255 (4)
C6	0.93412 (17)	−0.5598 (2)	0.32513 (17)	0.0267 (4)
C7	0.92689 (16)	−0.02356 (19)	0.34742 (15)	0.0224 (4)
H7A	0.971982	−0.080747	0.420318	0.027*
H7B	0.882538	0.066986	0.351566	0.027*
C8	0.81482 (17)	−0.0924 (2)	0.32549 (16)	0.0274 (4)
H8A	0.857409	−0.185325	0.325254	0.033*
H8B	0.770971	−0.037680	0.251702	0.033*
C9	0.70374 (17)	−0.1061 (2)	0.41151 (16)	0.0262 (4)
H9A	0.664389	−0.013924	0.414730	0.031*
H9B	0.746312	−0.165477	0.484817	0.031*
C10	0.58770 (17)	−0.1685 (2)	0.38420 (17)	0.0300 (5)
H10A	0.546505	−0.110648	0.311117	0.045*
H10B	0.516341	−0.173261	0.439346	0.045*
H10C	0.625754	−0.261643	0.384623	0.045*
C11	1.10593 (16)	−0.13536 (19)	0.24719 (15)	0.0220 (4)
H11A	1.034274	−0.168962	0.217291	0.026*
H11B	1.177309	−0.115180	0.191104	0.026*
C12	1.17300 (19)	−0.2504 (2)	0.34874 (16)	0.0291 (4)
H12A	1.104604	−0.269697	0.407353	0.035*
H12B	1.251077	−0.222371	0.376235	0.035*
C13	1.22608 (18)	−0.37964 (19)	0.32113 (17)	0.0283 (4)
H13A	1.293657	−0.358989	0.262000	0.034*
H13B	1.147464	−0.406106	0.292897	0.034*
C14	1.2952 (2)	−0.5005 (2)	0.42034 (19)	0.0389 (5)
H14A	1.374550	−0.475724	0.447544	0.058*
H14B	1.327294	−0.581133	0.398648	0.058*
H14C	1.228258	−0.522548	0.478674	0.058*
C15	1.14395 (15)	0.06092 (19)	0.30399 (15)	0.0216 (4)
H15A	1.093843	0.142392	0.319946	0.026*
H15B	1.186712	−0.007884	0.374330	0.026*
C16	1.25914 (16)	0.1048 (2)	0.22618 (15)	0.0239 (4)
H16A	1.218041	0.169146	0.153724	0.029*
H16B	1.316123	0.022741	0.215139	0.029*
C17	1.35122 (17)	0.1753 (2)	0.27221 (16)	0.0280 (4)
H17A	1.294010	0.257013	0.283628	0.034*
H17B	1.392453	0.110749	0.344569	0.034*
C18	1.46686 (18)	0.2203 (2)	0.19447 (17)	0.0332 (5)
H18A	1.527854	0.138786	0.187578	0.050*
H18B	1.520714	0.270043	0.223996	0.050*
H18C	1.426348	0.281070	0.121852	0.050*
C19	0.97771 (16)	0.09409 (18)	0.14931 (14)	0.0207 (4)
H19A	1.053150	0.099901	0.096272	0.025*
H19B	0.908733	0.050265	0.127099	0.025*
C20	0.90824 (17)	0.24005 (19)	0.13793 (16)	0.0259 (4)
H20A	0.972528	0.284576	0.164663	0.031*
H20B	0.824282	0.238287	0.182414	0.031*
C21	0.86853 (19)	0.3212 (2)	0.01593 (16)	0.0310 (5)
H21A	0.953720	0.323276	−0.027134	0.037*
H21B	0.808267	0.272688	−0.010449	0.037*
C22	0.7933 (2)	0.4686 (2)	−0.0051 (2)	0.0516 (7)
H22A	0.709623	0.467493	0.038254	0.077*
H22B	0.767219	0.514238	−0.083597	0.077*
H22C	0.854576	0.519104	0.016460	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.01826 (16)	0.02469 (19)	0.01825 (19)	−0.00601 (12)	0.00173 (12)	−0.00582 (15)
S1	0.0190 (2)	0.0269 (3)	0.0277 (3)	−0.00663 (17)	0.00041 (17)	−0.0037 (2)
S2	0.0193 (2)	0.0276 (3)	0.0200 (2)	−0.00756 (17)	0.00133 (17)	−0.0051 (2)
N1	0.0212 (7)	0.0251 (9)	0.0248 (9)	−0.0045 (6)	0.0014 (6)	−0.0087 (7)
N2	0.0194 (7)	0.0274 (9)	0.0236 (9)	−0.0042 (6)	0.0027 (6)	−0.0102 (7)
N3	0.0341 (8)	0.0265 (10)	0.0358 (11)	−0.0056 (7)	0.0003 (7)	−0.0111 (8)
N4	0.0294 (8)	0.0315 (10)	0.0534 (13)	−0.0031 (7)	−0.0063 (8)	−0.0132 (10)
N5	0.0183 (6)	0.0228 (8)	0.0174 (8)	−0.0036 (5)	0.0011 (5)	−0.0073 (7)
C1	0.0221 (8)	0.0257 (10)	0.0183 (9)	−0.0057 (7)	0.0030 (7)	−0.0091 (8)
C2	0.0210 (8)	0.0235 (9)	0.0186 (9)	−0.0043 (7)	0.0035 (6)	−0.0093 (8)
C3	0.0233 (8)	0.0239 (10)	0.0235 (10)	−0.0047 (7)	0.0028 (7)	−0.0097 (8)
C4	0.0217 (8)	0.0244 (10)	0.0249 (10)	−0.0028 (7)	0.0008 (7)	−0.0110 (8)
C5	0.0222 (8)	0.0294 (11)	0.0271 (11)	−0.0048 (7)	0.0015 (7)	−0.0128 (9)
C6	0.0226 (8)	0.0262 (10)	0.0329 (11)	−0.0053 (7)	0.0022 (8)	−0.0120 (9)
C7	0.0217 (8)	0.0255 (10)	0.0198 (10)	−0.0026 (7)	0.0040 (7)	−0.0089 (8)
C8	0.0244 (8)	0.0372 (12)	0.0237 (10)	−0.0090 (8)	0.0056 (7)	−0.0132 (9)
C9	0.0241 (8)	0.0273 (11)	0.0267 (11)	−0.0041 (7)	0.0056 (7)	−0.0096 (9)
C10	0.0262 (9)	0.0314 (11)	0.0284 (11)	−0.0070 (8)	0.0047 (8)	−0.0051 (9)
C11	0.0200 (8)	0.0246 (10)	0.0233 (10)	−0.0032 (7)	0.0030 (7)	−0.0118 (8)
C12	0.0318 (9)	0.0265 (11)	0.0270 (11)	0.0011 (8)	−0.0025 (8)	−0.0101 (9)
C13	0.0329 (9)	0.0207 (10)	0.0284 (11)	−0.0056 (7)	0.0082 (8)	−0.0054 (9)
C14	0.0421 (11)	0.0262 (11)	0.0424 (14)	0.0005 (9)	−0.0006 (10)	−0.0080 (11)
C15	0.0199 (8)	0.0251 (10)	0.0212 (10)	−0.0028 (7)	−0.0021 (7)	−0.0104 (8)
C16	0.0213 (8)	0.0301 (10)	0.0223 (10)	−0.0056 (7)	−0.0001 (7)	−0.0111 (9)
C17	0.0260 (9)	0.0361 (12)	0.0266 (11)	−0.0081 (8)	0.0002 (7)	−0.0156 (9)
C18	0.0287 (9)	0.0454 (13)	0.0313 (12)	−0.0152 (8)	0.0013 (8)	−0.0163 (11)
C19	0.0196 (7)	0.0261 (10)	0.0162 (9)	−0.0052 (7)	0.0008 (6)	−0.0068 (8)
C20	0.0267 (8)	0.0266 (10)	0.0226 (10)	−0.0017 (7)	−0.0008 (7)	−0.0080 (9)
C21	0.0336 (10)	0.0302 (11)	0.0243 (11)	−0.0013 (8)	−0.0063 (8)	−0.0053 (9)
C22	0.0662 (15)	0.0362 (14)	0.0351 (14)	0.0136 (11)	−0.0079 (12)	−0.0025 (12)

Geometric parameters (Å, º)

Ni1—S1	2.1606 (5)	C11—H11B	0.9900
Ni1—S1^i	2.1607 (5)	C12—C13	1.522 (3)
Ni1—S2	2.1759 (5)	C12—H12A	0.9900
Ni1—S2^i	2.1759 (5)	C12—H12B	0.9900
S1—C1	1.7229 (17)	C13—C14	1.523 (3)
S2—C2	1.7159 (19)	C13—H13A	0.9900
N1—C1	1.325 (2)	C13—H13B	0.9900
N1—C3	1.351 (2)	C14—H14A	0.9800
N2—C2	1.335 (2)	C14—H14B	0.9800
N2—C4	1.345 (2)	C14—H14C	0.9800
N3—C5	1.144 (2)	C15—C16	1.519 (2)
N4—C6	1.147 (2)	C15—H15A	0.9900
N5—C19	1.519 (2)	C15—H15B	0.9900
N5—C7	1.521 (2)	C16—C17	1.526 (2)
N5—C15	1.525 (2)	C16—H16A	0.9900
N5—C11	1.523 (2)	C16—H16B	0.9900
C1—C2	1.451 (2)	C17—C18	1.525 (2)
C3—C4	1.395 (2)	C17—H17A	0.9900
C3—C5	1.443 (3)	C17—H17B	0.9900
C4—C6	1.448 (2)	C18—H18A	0.9800
C7—C8	1.512 (2)	C18—H18B	0.9800
C7—H7A	0.9900	C18—H18C	0.9800
C7—H7B	0.9900	C19—C20	1.517 (2)
C8—C9	1.524 (2)	C19—H19A	0.9900
C8—H8A	0.9900	C19—H19B	0.9900
C8—H8B	0.9900	C20—C21	1.534 (3)
C9—C10	1.527 (3)	C20—H20A	0.9900
C9—H9A	0.9900	C20—H20B	0.9900
C9—H9B	0.9900	C21—C22	1.521 (3)
C10—H10A	0.9800	C21—H21A	0.9900
C10—H10B	0.9800	C21—H21B	0.9900
C10—H10C	0.9800	C22—H22A	0.9800
C11—C12	1.507 (3)	C22—H22B	0.9800
C11—H11A	0.9900	C22—H22C	0.9800
S1—Ni1—S1^i	180.0	C11—C12—H12B	109.8
S1—Ni1—S2	91.724 (19)	C13—C12—H12B	109.8
S1^i—Ni1—S2	88.275 (19)	H12A—C12—H12B	108.2
S1—Ni1—S2^i	88.275 (19)	C12—C13—C14	112.47 (17)
S1^i—Ni1—S2^i	91.725 (19)	C12—C13—H13A	109.1
S2—Ni1—S2^i	180.0	C14—C13—H13A	109.1
C1—S1—Ni1	105.40 (6)	C12—C13—H13B	109.1
C2—S2—Ni1	104.96 (6)	C14—C13—H13B	109.1
C1—N1—C3	116.12 (15)	H13A—C13—H13B	107.8
C2—N2—C4	116.28 (14)	C13—C14—H14A	109.5
C19—N5—C7	111.36 (12)	C13—C14—H14B	109.5
C19—N5—C15	111.42 (13)	H14A—C14—H14B	109.5
C7—N5—C15	106.35 (13)	C13—C14—H14C	109.5
C19—N5—C11	105.17 (13)	H14A—C14—H14C	109.5
C7—N5—C11	111.23 (13)	H14B—C14—H14C	109.5
C15—N5—C11	111.41 (12)	C16—C15—N5	115.56 (14)
N1—C1—C2	122.13 (15)	C16—C15—H15A	108.4
N1—C1—S1	119.28 (13)	N5—C15—H15A	108.4
C2—C1—S1	118.59 (14)	C16—C15—H15B	108.4
N2—C2—C1	120.75 (16)	N5—C15—H15B	108.4
N2—C2—S2	120.08 (13)	H15A—C15—H15B	107.5
C1—C2—S2	119.17 (13)	C15—C16—C17	110.93 (15)
N1—C3—C4	121.96 (17)	C15—C16—H16A	109.5
N1—C3—C5	118.20 (15)	C17—C16—H16A	109.5
C4—C3—C5	119.84 (16)	C15—C16—H16B	109.5
N2—C4—C3	122.75 (15)	C17—C16—H16B	109.5
N2—C4—C6	119.19 (15)	H16A—C16—H16B	108.0
C3—C4—C6	118.05 (17)	C18—C17—C16	111.35 (16)
N3—C5—C3	176.02 (18)	C18—C17—H17A	109.4
N4—C6—C4	175.5 (2)	C16—C17—H17A	109.4
C8—C7—N5	115.26 (15)	C18—C17—H17B	109.4
C8—C7—H7A	108.5	C16—C17—H17B	109.4
N5—C7—H7A	108.5	H17A—C17—H17B	108.0
C8—C7—H7B	108.5	C17—C18—H18A	109.5
N5—C7—H7B	108.5	C17—C18—H18B	109.5
H7A—C7—H7B	107.5	H18A—C18—H18B	109.5
C7—C8—C9	112.11 (16)	C17—C18—H18C	109.5
C7—C8—H8A	109.2	H18A—C18—H18C	109.5
C9—C8—H8A	109.2	H18B—C18—H18C	109.5
C7—C8—H8B	109.2	C20—C19—N5	117.09 (15)
C9—C8—H8B	109.2	C20—C19—H19A	108.0
H8A—C8—H8B	107.9	N5—C19—H19A	108.0
C8—C9—C10	111.19 (16)	C20—C19—H19B	108.0
C8—C9—H9A	109.4	N5—C19—H19B	108.0
C10—C9—H9A	109.4	H19A—C19—H19B	107.3
C8—C9—H9B	109.4	C19—C20—C21	108.27 (16)
C10—C9—H9B	109.4	C19—C20—H20A	110.0
H9A—C9—H9B	108.0	C21—C20—H20A	110.0
C9—C10—H10A	109.5	C19—C20—H20B	110.0
C9—C10—H10B	109.5	C21—C20—H20B	110.0
H10A—C10—H10B	109.5	H20A—C20—H20B	108.4
C9—C10—H10C	109.5	C22—C21—C20	112.99 (18)
H10A—C10—H10C	109.5	C22—C21—H21A	109.0
H10B—C10—H10C	109.5	C20—C21—H21A	109.0
C12—C11—N5	116.35 (15)	C22—C21—H21B	109.0
C12—C11—H11A	108.2	C20—C21—H21B	109.0
N5—C11—H11A	108.2	H21A—C21—H21B	107.8
C12—C11—H11B	108.2	C21—C22—H22A	109.5
N5—C11—H11B	108.2	C21—C22—H22B	109.5
H11A—C11—H11B	107.4	H22A—C22—H22B	109.5
C11—C12—C13	109.60 (16)	C21—C22—H22C	109.5
C11—C12—H12A	109.8	H22A—C22—H22C	109.5
C13—C12—H12A	109.8	H22B—C22—H22C	109.5
C3—N1—C1—C2	0.7 (3)	C19—N5—C7—C8	61.82 (19)
C3—N1—C1—S1	−178.76 (14)	C15—N5—C7—C8	−176.62 (15)
Ni1—S1—C1—N1	176.83 (13)	C11—N5—C7—C8	−55.14 (19)
Ni1—S1—C1—C2	−2.61 (16)	N5—C7—C8—C9	−177.56 (14)
C4—N2—C2—C1	−0.3 (3)	C7—C8—C9—C10	176.84 (16)
C4—N2—C2—S2	179.10 (13)	C19—N5—C11—C12	−178.87 (14)
N1—C1—C2—N2	−0.2 (3)	C7—N5—C11—C12	−58.20 (19)
S1—C1—C2—N2	179.21 (14)	C15—N5—C11—C12	60.28 (19)
N1—C1—C2—S2	−179.64 (14)	N5—C11—C12—C13	176.10 (14)
S1—C1—C2—S2	−0.2 (2)	C11—C12—C13—C14	−179.93 (15)
Ni1—S2—C2—N2	−176.53 (13)	C19—N5—C15—C16	−53.08 (18)
Ni1—S2—C2—C1	2.90 (15)	C7—N5—C15—C16	−174.61 (14)
C1—N1—C3—C4	−0.6 (3)	C11—N5—C15—C16	64.03 (19)
C1—N1—C3—C5	179.27 (16)	N5—C15—C16—C17	175.43 (14)
C2—N2—C4—C3	0.4 (3)	C15—C16—C17—C18	−179.76 (15)
C2—N2—C4—C6	−179.57 (17)	C7—N5—C19—C20	61.98 (19)
N1—C3—C4—N2	0.1 (3)	C15—N5—C19—C20	−56.59 (18)
C5—C3—C4—N2	−179.79 (17)	C11—N5—C19—C20	−177.43 (14)
N1—C3—C4—C6	−179.97 (17)	N5—C19—C20—C21	174.11 (14)
C5—C3—C4—C6	0.2 (3)	C19—C20—C21—C22	178.07 (17)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···N4^ii	0.99	2.59	3.559 (3)	166
C13—H13A···S1^iii	0.99	2.82	3.748 (2)	157

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