Bis[1-(4-nitro­benz­yl)pyridinium] bis­(2,2-dicyano­ethyl­ene-1,1-dithiol­ato-κ²S,S′)nickelate(II)

In the new ion-pair title complex, (C₁₂H₁₁N₂O₂)₂[Ni(C₄N₂S₂)₂] or 2(NO₂BzPy)⁺·[Ni(i-mnt)₂]²⁻, where NO₂BzPy⁺ is 1-(4-nitro­benz­yl)pyridinium and i-mnt is 2,2-dicyano­ethyl­ene-1,1-dithiol­ate, the [Ni(i-mnt)₂]²⁻ complex anion lies on an inversion centre and exhibits an almost structure. Weak C—H...N and C—H...Ni contacts are observed between anions and cations in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.054
• wR factor = 0.095
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C2     -   C3     ...       1.42 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C2     -   C4     ...       1.42 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K

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

   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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-(4-nitrobenzyl)pyridinium] bis(2,2-dicyanoethylene-1,1-dithiolato-κ²S,S')nickel(II)

Crystal data

(C12H11N2O2)2[Ni(C4N2S2)2]	F(000) = 788
Mr = 769.53	Dx = 1.491 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 607 reflections
a = 9.825 (1) Å	θ = 2.7–26.5°
b = 12.092 (1) Å	µ = 0.86 mm^−1
c = 14.660 (2) Å	T = 293 K
β = 100.11 (1)°	Block, brown
V = 1714.6 (3) Å^3	0.46 × 0.32 × 0.24 mm
Z = 2

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3017 independent reflections
Radiation source: fine-focus sealed tube	1649 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.073
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.716, Tmax = 0.804	k = −14→12
16784 measured reflections	l = −17→15

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	H-atom parameters constrained
S = 0.85	w = 1/[σ^2(Fo^2) + (0.03P)^2] where P = (Fo^2 + 2Fc^2)/3
3017 reflections	(Δ/σ)max < 0.001
223 parameters	Δρmax = 0.35 e Å^−3
2 restraints	Δρmin = −0.27 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.0000	0.0000	0.0000	0.0459 (2)
S1	−0.10543 (12)	0.15741 (9)	0.01222 (9)	0.0564 (4)
S2	0.17713 (11)	0.11399 (9)	0.02447 (8)	0.0534 (3)
N1	−0.1117 (4)	0.4509 (3)	0.0844 (3)	0.0822 (14)
N2	0.3353 (4)	0.3941 (3)	0.0902 (3)	0.0806 (14)
N3	0.9123 (4)	1.0135 (3)	0.2841 (3)	0.0523 (10)
N4	1.0560 (5)	0.4937 (4)	0.3312 (3)	0.0674 (12)
O1	1.0226 (4)	0.4438 (3)	0.3963 (3)	0.0976 (13)
O2	1.1361 (4)	0.4583 (3)	0.2845 (3)	0.0926 (13)
C1	0.0577 (4)	0.2150 (3)	0.0357 (3)	0.0471 (11)
C2	0.0870 (5)	0.3222 (3)	0.0622 (3)	0.0481 (11)
C3	−0.0223 (5)	0.3942 (4)	0.0748 (3)	0.0569 (13)
C4	0.2247 (5)	0.3633 (4)	0.0781 (3)	0.0556 (13)
C5	0.8601 (4)	0.7541 (4)	0.3465 (3)	0.0605 (13)
H5	0.8054	0.7860	0.3851	0.073*
C6	0.9183 (5)	0.6513 (4)	0.3678 (3)	0.0627 (13)
H6	0.9049	0.6144	0.4212	0.075*
C7	0.9958 (5)	0.6050 (4)	0.3094 (3)	0.0496 (12)
C8	1.0183 (5)	0.6561 (4)	0.2313 (3)	0.0625 (13)
H8	1.0713	0.6227	0.1924	0.075*
C9	0.9600 (5)	0.7601 (4)	0.2106 (3)	0.0672 (14)
H9	0.9738	0.7966	0.1571	0.081*
C10	0.8822 (4)	0.8093 (3)	0.2690 (3)	0.0496 (12)
C11	0.8193 (4)	0.9214 (3)	0.2448 (3)	0.0612 (14)
H11A	0.7985	0.9289	0.1779	0.073*
H11B	0.7329	0.9269	0.2680	0.073*
C12	0.8938 (5)	1.0647 (4)	0.3610 (4)	0.0692 (15)
H12	0.8239	1.0414	0.3919	0.083*
C13	0.9763 (6)	1.1508 (4)	0.3951 (4)	0.0848 (17)
H13	0.9618	1.1875	0.4483	0.102*
C14	1.0806 (6)	1.1828 (4)	0.3505 (4)	0.0796 (17)
H14	1.1378	1.2415	0.3734	0.095*
C15	1.1007 (5)	1.1287 (4)	0.2726 (4)	0.0751 (16)
H15	1.1717	1.1494	0.2417	0.090*
C16	1.0150 (6)	1.0440 (4)	0.2410 (3)	0.0674 (14)
H16	1.0282	1.0061	0.1880	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0456 (5)	0.0457 (5)	0.0459 (5)	0.0053 (4)	0.0069 (4)	−0.0042 (4)
S1	0.0427 (7)	0.0497 (7)	0.0768 (9)	0.0037 (6)	0.0103 (6)	−0.0070 (6)
S2	0.0445 (7)	0.0520 (7)	0.0625 (8)	0.0076 (6)	0.0061 (6)	−0.0049 (6)
N1	0.072 (3)	0.056 (3)	0.124 (4)	0.007 (2)	0.033 (3)	−0.001 (3)
N2	0.058 (3)	0.083 (3)	0.098 (4)	−0.007 (3)	0.005 (3)	−0.008 (2)
N3	0.055 (3)	0.052 (2)	0.049 (2)	0.006 (2)	0.007 (2)	0.006 (2)
N4	0.069 (3)	0.053 (3)	0.076 (3)	−0.004 (3)	0.002 (3)	−0.006 (3)
O1	0.119 (3)	0.066 (2)	0.116 (4)	0.006 (2)	0.043 (3)	0.027 (2)
O2	0.100 (3)	0.081 (3)	0.096 (3)	0.030 (2)	0.016 (3)	−0.009 (2)
C1	0.045 (3)	0.049 (3)	0.046 (3)	0.006 (2)	0.004 (2)	0.000 (2)
C2	0.048 (2)	0.043 (3)	0.052 (3)	0.006 (2)	0.006 (2)	−0.001 (2)
C3	0.060 (4)	0.042 (3)	0.069 (4)	−0.007 (3)	0.014 (3)	0.004 (3)
C4	0.051 (3)	0.052 (3)	0.062 (3)	0.005 (3)	0.005 (3)	−0.008 (2)
C5	0.056 (3)	0.055 (3)	0.077 (4)	0.010 (3)	0.029 (3)	0.001 (3)
C6	0.061 (3)	0.064 (3)	0.066 (4)	−0.007 (3)	0.019 (3)	0.010 (3)
C7	0.047 (3)	0.048 (3)	0.054 (3)	−0.005 (2)	0.009 (3)	−0.004 (2)
C8	0.070 (4)	0.064 (3)	0.056 (3)	0.007 (3)	0.015 (3)	−0.014 (3)
C9	0.088 (4)	0.065 (3)	0.047 (3)	0.004 (3)	0.008 (3)	0.003 (3)
C10	0.043 (3)	0.048 (3)	0.054 (3)	0.002 (2)	−0.002 (3)	−0.008 (2)
C11	0.052 (3)	0.059 (3)	0.066 (3)	0.001 (3)	−0.006 (3)	−0.002 (3)
C12	0.067 (4)	0.068 (3)	0.079 (4)	−0.012 (3)	0.031 (3)	−0.015 (3)
C13	0.089 (5)	0.071 (4)	0.102 (5)	−0.016 (3)	0.037 (4)	−0.034 (3)
C14	0.071 (4)	0.049 (3)	0.117 (5)	−0.010 (3)	0.013 (4)	0.004 (3)
C15	0.072 (4)	0.070 (4)	0.088 (5)	−0.007 (3)	0.026 (3)	0.013 (3)
C16	0.077 (4)	0.070 (4)	0.059 (4)	0.009 (3)	0.021 (3)	0.011 (3)

Geometric parameters (Å, º)

Ni1—S1	2.1894 (11)	C6—C7	1.363 (6)
Ni1—S1^i	2.1894 (11)	C6—H6	0.9300
Ni1—S2	2.1996 (11)	C7—C8	1.352 (6)
Ni1—S2^i	2.1996 (11)	C8—C9	1.393 (5)
S1—C1	1.725 (4)	C8—H8	0.9300
S2—C1	1.721 (4)	C9—C10	1.378 (6)
N1—C3	1.142 (5)	C9—H9	0.9300
N2—C4	1.133 (5)	C10—C11	1.507 (5)
N3—C12	1.325 (5)	C11—H11A	0.9700
N3—C16	1.334 (6)	C11—H11B	0.9700
N3—C11	1.491 (5)	C12—C13	1.360 (6)
N4—O2	1.210 (5)	C12—H12	0.9300
N4—O1	1.221 (5)	C13—C14	1.365 (7)
N4—C7	1.482 (5)	C13—H13	0.9300
C1—C2	1.370 (5)	C14—C15	1.361 (7)
C2—C3	1.419 (6)	C14—H14	0.9300
C2—C4	1.421 (6)	C15—C16	1.355 (6)
C5—C10	1.367 (6)	C15—H15	0.9300
C5—C6	1.381 (5)	C16—H16	0.9300
C5—H5	0.9300
S1—Ni1—S1^i	180.00 (8)	C7—C8—C9	118.4 (5)
S1—Ni1—S2	79.28 (4)	C7—C8—H8	120.8
S1^i—Ni1—S2	100.72 (4)	C9—C8—H8	120.8
S1—Ni1—S2^i	100.72 (4)	C10—C9—C8	120.4 (5)
S1^i—Ni1—S2^i	79.28 (4)	C10—C9—H9	119.8
S2—Ni1—S2^i	180.00 (8)	C8—C9—H9	119.8
C1—S1—Ni1	86.03 (14)	C5—C10—C9	119.5 (4)
C1—S2—Ni1	85.80 (15)	C5—C10—C11	121.1 (4)
C12—N3—C16	120.1 (4)	C9—C10—C11	119.4 (5)
C12—N3—C11	120.8 (4)	N3—C11—C10	112.5 (3)
C16—N3—C11	119.1 (4)	N3—C11—H11A	109.1
O2—N4—O1	124.0 (5)	C10—C11—H11A	109.1
O2—N4—C7	118.2 (5)	N3—C11—H11B	109.1
O1—N4—C7	117.8 (5)	C10—C11—H11B	109.1
C2—C1—S2	125.8 (3)	H11A—C11—H11B	107.8
C2—C1—S1	125.5 (3)	N3—C12—C13	120.6 (5)
S2—C1—S1	108.7 (2)	N3—C12—H12	119.7
C1—C2—C3	119.4 (4)	C13—C12—H12	119.7
C1—C2—C4	121.6 (4)	C12—C13—C14	119.4 (5)
C3—C2—C4	119.0 (4)	C12—C13—H13	120.3
N1—C3—C2	178.9 (5)	C14—C13—H13	120.3
N2—C4—C2	178.7 (5)	C15—C14—C13	119.8 (5)
C10—C5—C6	120.5 (4)	C15—C14—H14	120.1
C10—C5—H5	119.8	C13—C14—H14	120.1
C6—C5—H5	119.8	C16—C15—C14	118.5 (5)
C7—C6—C5	118.9 (5)	C16—C15—H15	120.7
C7—C6—H6	120.6	C14—C15—H15	120.7
C5—C6—H6	120.6	N3—C16—C15	121.5 (5)
C8—C7—C6	122.4 (5)	N3—C16—H16	119.2
C8—C7—N4	118.7 (5)	C15—C16—H16	119.2
C6—C7—N4	118.9 (5)

Symmetry code: (i) −x, −y, −z.