Bis­[1-(3-cyano­benzyl)-3-methyl­pyrazinium] bis(1,2-di­cyano­ethene-1,2-di­thiol­ato)­nickel(II)

In the title complex, (C₁₃H₁₂N₃)₂[Ni(C₄N₂S₂)₂], the anion has slightly disorted square-planar coordination geometry, in which the Ni atom lies on an inversion center. In the crystal structure, weak C—H...N interactions connect anions and cations into a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.055
• wR factor = 0.133
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C12    -   C17    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C2     ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C3     -   C4     ...       1.43 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C13 H12 N3

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

   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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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.

Bis[1-(3-cyanobenzyl)-3-methylpyrazinium] bis(1,2-dicyanoethene-1,2-dithiolato)nickel(II)

Crystal data

(C13H12N3)2[Ni(C4N2S2)2]	F(000) = 780
Mr = 759.58	Dx = 1.447 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 951 reflections
a = 8.831 (2) Å	θ = 2.7–26.4°
b = 14.220 (2) Å	µ = 0.84 mm^−1
c = 14.256 (2) Å	T = 293 K
β = 103.10 (1)°	Block, red
V = 1743.6 (5) Å^3	0.3 × 0.25 × 0.2 mm
Z = 2

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3401 independent reflections
Radiation source: sealed tube	2473 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
Tmin = 0.77, Tmax = 0.84	k = −17→17
9111 measured reflections	l = −10→17

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.06P)^2 + 1.99P] where P = (Fo^2 + 2Fc^2)/3
3401 reflections	(Δ/σ)max < 0.001
224 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.34 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
Ni1	1.0000	0.5000	0.0000	0.0490 (2)
S1	0.91760 (11)	0.40198 (7)	0.09433 (7)	0.0511 (2)
S2	0.80570 (11)	0.59381 (6)	−0.00389 (7)	0.0506 (2)
N1	0.6118 (5)	0.3725 (3)	0.2293 (3)	0.0774 (11)
N2	0.4732 (4)	0.6331 (3)	0.1062 (3)	0.0764 (11)
C1	0.6733 (5)	0.4110 (3)	0.1795 (3)	0.0534 (9)
C2	0.7534 (4)	0.4587 (3)	0.1159 (2)	0.0453 (8)
C3	0.7065 (4)	0.5399 (2)	0.0733 (2)	0.0439 (8)
C4	0.5756 (4)	0.5899 (3)	0.0923 (3)	0.0524 (9)
N3	1.1059 (3)	0.6681 (2)	0.19793 (19)	0.0442 (6)
N4	0.9137 (4)	0.8148 (2)	0.1328 (3)	0.0594 (8)
N5	1.1716 (5)	0.4414 (3)	0.6131 (3)	0.0867 (13)
C5	1.1320 (4)	0.7208 (3)	0.1274 (3)	0.0514 (9)
H5	1.2158	0.7084	0.0999	0.062*
C6	1.0335 (5)	0.7942 (3)	0.0953 (3)	0.0650 (11)
H6	1.0516	0.8311	0.0450	0.078*
C7	0.8901 (4)	0.7623 (3)	0.2038 (3)	0.0484 (8)
C8	0.9829 (4)	0.6871 (2)	0.2367 (2)	0.0452 (8)
H8	0.9617	0.6491	0.2853	0.054*
C9	1.2055 (5)	0.5843 (2)	0.2328 (3)	0.0535 (9)
H9A	1.1422	0.5279	0.2222	0.064*
H9B	1.2851	0.5785	0.1962	0.064*
C10	1.2809 (4)	0.5925 (2)	0.3374 (2)	0.0427 (7)
C11	1.2251 (4)	0.5379 (2)	0.4025 (3)	0.0478 (8)
H11	1.1439	0.4961	0.3804	0.057*
C12	1.2895 (4)	0.5451 (3)	0.5007 (3)	0.0504 (9)
C13	1.4094 (5)	0.6081 (3)	0.5330 (3)	0.0603 (10)
H13	1.4516	0.6141	0.5987	0.072*
C14	1.4657 (5)	0.6612 (3)	0.4697 (3)	0.0631 (11)
H14	1.5471	0.7029	0.4918	0.076*
C15	1.4023 (5)	0.6533 (3)	0.3725 (3)	0.0556 (9)
H15	1.4421	0.6898	0.3296	0.067*
C16	0.7533 (5)	0.7843 (3)	0.2477 (3)	0.0682 (12)
H16A	0.6588	0.7816	0.1986	0.102*
H16B	0.7654	0.8462	0.2753	0.102*
H16C	0.7488	0.7391	0.2970	0.102*
C17	1.2269 (5)	0.4865 (3)	0.5653 (3)	0.0649 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0459 (4)	0.0529 (4)	0.0520 (4)	0.0030 (3)	0.0191 (3)	0.0067 (3)
S1	0.0477 (5)	0.0548 (5)	0.0549 (5)	0.0043 (4)	0.0202 (4)	0.0088 (4)
S2	0.0476 (5)	0.0534 (5)	0.0551 (5)	0.0040 (4)	0.0205 (4)	0.0083 (4)
N1	0.089 (3)	0.087 (3)	0.068 (2)	−0.016 (2)	0.043 (2)	0.001 (2)
N2	0.061 (2)	0.080 (2)	0.099 (3)	0.0026 (19)	0.039 (2)	−0.007 (2)
C1	0.060 (2)	0.058 (2)	0.046 (2)	−0.0081 (17)	0.0199 (18)	−0.0062 (17)
C2	0.0408 (18)	0.057 (2)	0.0402 (17)	−0.0063 (15)	0.0143 (15)	−0.0019 (16)
C3	0.0392 (18)	0.0514 (19)	0.0438 (18)	−0.0063 (14)	0.0152 (14)	−0.0113 (15)
C4	0.044 (2)	0.059 (2)	0.058 (2)	−0.0072 (17)	0.0175 (17)	−0.0074 (18)
N3	0.0406 (15)	0.0503 (16)	0.0410 (15)	0.0027 (12)	0.0075 (12)	−0.0051 (13)
N4	0.058 (2)	0.0488 (18)	0.071 (2)	0.0047 (15)	0.0139 (17)	0.0079 (16)
N5	0.091 (3)	0.099 (3)	0.079 (3)	−0.007 (2)	0.038 (2)	0.026 (2)
C5	0.046 (2)	0.062 (2)	0.050 (2)	−0.0043 (16)	0.0183 (17)	0.0053 (17)
C6	0.072 (3)	0.054 (2)	0.074 (3)	0.0016 (19)	0.027 (2)	0.016 (2)
C7	0.0393 (18)	0.053 (2)	0.051 (2)	−0.0017 (15)	0.0057 (15)	−0.0122 (17)
C8	0.0441 (18)	0.056 (2)	0.0375 (17)	−0.0012 (15)	0.0125 (14)	0.0015 (15)
C9	0.057 (2)	0.048 (2)	0.055 (2)	0.0130 (16)	0.0097 (17)	−0.0043 (17)
C10	0.0422 (18)	0.0415 (17)	0.0444 (18)	0.0055 (14)	0.0098 (14)	0.0003 (14)
C11	0.0440 (19)	0.0457 (18)	0.054 (2)	−0.0017 (15)	0.0110 (16)	0.0003 (16)
C12	0.053 (2)	0.049 (2)	0.054 (2)	0.0066 (16)	0.0211 (17)	0.0055 (17)
C13	0.057 (2)	0.071 (3)	0.053 (2)	0.0019 (19)	0.0105 (18)	−0.0060 (19)
C14	0.058 (2)	0.062 (2)	0.067 (3)	−0.0195 (19)	0.009 (2)	−0.003 (2)
C15	0.058 (2)	0.051 (2)	0.060 (2)	−0.0044 (17)	0.0186 (19)	0.0058 (18)
C16	0.050 (2)	0.079 (3)	0.076 (3)	0.009 (2)	0.017 (2)	−0.017 (2)
C17	0.067 (3)	0.070 (3)	0.062 (2)	0.003 (2)	0.023 (2)	0.010 (2)

Geometric parameters (Å, º)

Ni1—S2	2.1642 (10)	C7—C8	1.365 (5)
Ni1—S2^i	2.1642 (10)	C7—C16	1.514 (5)
Ni1—S1	2.1735 (9)	C8—H8	0.9300
Ni1—S1^i	2.1735 (9)	C9—C10	1.494 (5)
S1—C2	1.746 (4)	C9—H9A	0.9700
S2—C3	1.732 (3)	C9—H9B	0.9700
N1—C1	1.129 (5)	C10—C15	1.380 (5)
N2—C4	1.147 (5)	C10—C11	1.382 (5)
C1—C2	1.440 (5)	C11—C12	1.390 (5)
C2—C3	1.327 (5)	C11—H11	0.9300
C3—C4	1.434 (5)	C12—C13	1.384 (5)
N3—C5	1.316 (4)	C12—C17	1.441 (5)
N3—C8	1.353 (4)	C13—C14	1.355 (6)
N3—C9	1.497 (4)	C13—H13	0.9300
N4—C7	1.311 (5)	C14—C15	1.376 (5)
N4—C6	1.322 (5)	C14—H14	0.9300
N5—C17	1.125 (5)	C15—H15	0.9300
C5—C6	1.369 (5)	C16—H16A	0.9600
C5—H5	0.9300	C16—H16B	0.9600
C6—H6	0.9300	C16—H16C	0.9600
S2—Ni1—S2^i	180.0	C10—C9—N3	111.4 (3)
S2—Ni1—S1	92.09 (4)	C10—C9—H9A	109.3
S2^i—Ni1—S1	87.91 (4)	N3—C9—H9A	109.3
S2—Ni1—S1^i	87.91 (4)	C10—C9—H9B	109.3
S2^i—Ni1—S1^i	92.09 (4)	N3—C9—H9B	109.3
S1—Ni1—S1^i	180.0	H9A—C9—H9B	108.0
C2—S1—Ni1	102.72 (12)	C15—C10—C11	118.3 (3)
C3—S2—Ni1	102.90 (13)	C15—C10—C9	123.0 (3)
N1—C1—C2	179.0 (5)	C11—C10—C9	118.7 (3)
C3—C2—C1	123.4 (3)	C10—C11—C12	120.6 (3)
C3—C2—S1	120.5 (2)	C10—C11—H11	119.7
C1—C2—S1	116.0 (3)	C12—C11—H11	119.7
C2—C3—C4	121.7 (3)	C13—C12—C11	119.3 (3)
C2—C3—S2	121.7 (3)	C13—C12—C17	122.5 (4)
C4—C3—S2	116.5 (3)	C11—C12—C17	118.3 (4)
N2—C4—C3	177.2 (4)	C14—C13—C12	120.5 (4)
C5—N3—C8	119.6 (3)	C14—C13—H13	119.7
C5—N3—C9	121.0 (3)	C12—C13—H13	119.7
C8—N3—C9	119.3 (3)	C13—C14—C15	119.9 (4)
C7—N4—C6	117.9 (3)	C13—C14—H14	120.1
N3—C5—C6	118.8 (3)	C15—C14—H14	120.1
N3—C5—H5	120.6	C14—C15—C10	121.5 (3)
C6—C5—H5	120.6	C14—C15—H15	119.3
N4—C6—C5	122.6 (4)	C10—C15—H15	119.3
N4—C6—H6	118.7	C7—C16—H16A	109.5
C5—C6—H6	118.7	C7—C16—H16B	109.5
N4—C7—C8	121.5 (3)	H16A—C16—H16B	109.5
N4—C7—C16	118.9 (3)	C7—C16—H16C	109.5
C8—C7—C16	119.6 (3)	H16A—C16—H16C	109.5
N3—C8—C7	119.5 (3)	H16B—C16—H16C	109.5
N3—C8—H8	120.3	N5—C17—C12	176.9 (5)
C7—C8—H8	120.3

Symmetry code: (i) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N2^ii	0.93	2.50	3.338 (5)	151
C8—H8···N5^iii	0.93	2.43	3.333 (5)	163
C9—H9B···N2^ii	0.97	2.44	3.356 (5)	157

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