Buy article online - an online subscription or single-article purchase is required to access this article.
In the title complex, (C
13H
12N
3)
2[Ni(C
4N
2S
2)
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.
Supporting information
CCDC reference: 238643
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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)
top
Crystal data top
(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) Å3 | 0.3 × 0.25 × 0.2 mm |
Z = 2 | |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.06P)2 + 1.99P] where P = (Fo2 + 2Fc2)/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 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. |
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
Ni1—S2 | 2.1642 (10) | C7—C8 | 1.365 (5) |
Ni1—S2i | 2.1642 (10) | C7—C16 | 1.514 (5) |
Ni1—S1 | 2.1735 (9) | C8—H8 | 0.9300 |
Ni1—S1i | 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—S2i | 180.0 | C10—C9—N3 | 111.4 (3) |
S2—Ni1—S1 | 92.09 (4) | C10—C9—H9A | 109.3 |
S2i—Ni1—S1 | 87.91 (4) | N3—C9—H9A | 109.3 |
S2—Ni1—S1i | 87.91 (4) | C10—C9—H9B | 109.3 |
S2i—Ni1—S1i | 92.09 (4) | N3—C9—H9B | 109.3 |
S1—Ni1—S1i | 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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···N2ii | 0.93 | 2.50 | 3.338 (5) | 151 |
C8—H8···N5iii | 0.93 | 2.43 | 3.333 (5) | 163 |
C9—H9B···N2ii | 0.97 | 2.44 | 3.356 (5) | 157 |
Symmetry codes: (ii) x+1, y, z; (iii) −x+2, −y+1, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.