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The asymmetric unit of the title compound, (C12H12ClN2)[Ni(C4N2S2)2], consists of one 2-amino-1-(4-chloro­benzyl)­pyridinium cation and one [Ni(mnt)2]- anion (where mnt is 1,2-dicyano­ethene-1,2-dithiol­ate or maleonitrile­dithiol­ate). The NiIII ion is coordinated by four S atoms of two mnt ligands and exhibits the expected square-planar coordination geometry. The anions and cations stack into well segregated columns along the a axis and the NiIII atoms form a zigzag chain.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806014450/bt2061sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806014450/bt2061Isup2.hkl
Contains datablock I

CCDC reference: 608380

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.046
  • wR factor = 0.079
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K 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 ... 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C5 - C6 ... 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C7 - C8 ... 1.44 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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.

2-Amino-1-(4-chlorobenzyl)pyridinium bis(1,2-dicyanoethene-1,2-dithiolato)nickelate(III) top
Crystal data top
(C12H12ClN2)[Ni(C4N2S2)2]Z = 2
Mr = 558.76F(000) = 566
Triclinic, P1Dx = 1.629 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.891 (1) ÅCell parameters from 1490 reflections
b = 10.629 (2) Åθ = 2.6–25.5°
c = 16.378 (3) ŵ = 1.36 mm1
α = 104.85 (1)°T = 293 K
β = 96.38 (1)°Block, black
γ = 96.66 (1)°0.4 × 0.35 × 0.3 mm
V = 1139.2 (3) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3944 independent reflections
Radiation source: sealed tube2731 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 78
Tmin = 0.576, Tmax = 0.657k = 129
5709 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.015P)2]
where P = (Fo2 + 2Fc2)/3
3944 reflections(Δ/σ)max = 0.001
289 parametersΔρmax = 0.59 e Å3
0 restraintsΔρmin = 0.39 e Å3
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
xyzUiso*/Ueq
Ni10.72511 (7)0.51283 (5)0.43224 (3)0.03369 (15)
S10.70868 (16)0.60184 (10)0.32863 (6)0.0424 (3)
S20.65797 (16)0.31836 (10)0.34822 (6)0.0425 (3)
S30.74032 (15)0.42211 (10)0.53471 (6)0.0394 (3)
S40.80681 (16)0.70623 (10)0.51724 (6)0.0440 (3)
Cl10.81037 (17)1.00778 (13)0.41840 (8)0.0688 (4)
N10.6451 (6)0.5152 (4)0.0943 (2)0.0696 (13)
N20.5751 (6)0.1383 (4)0.1208 (2)0.0697 (13)
N30.8352 (5)0.5071 (4)0.7699 (2)0.0540 (11)
N40.9373 (6)0.8718 (4)0.7496 (2)0.0650 (12)
N50.0106 (5)0.7872 (3)0.11918 (19)0.0405 (9)
N60.1836 (5)0.6238 (3)0.0795 (2)0.0603 (11)
H6A0.20570.62060.13160.072*
H6B0.23490.57290.04060.072*
C10.6493 (6)0.4945 (4)0.1587 (3)0.0466 (12)
C20.6585 (5)0.4681 (4)0.2408 (2)0.0370 (10)
C30.6380 (5)0.3453 (4)0.2486 (2)0.0378 (10)
C40.6014 (6)0.2298 (5)0.1767 (3)0.0476 (12)
C50.8226 (6)0.5276 (4)0.7052 (2)0.0354 (10)
C60.8053 (5)0.5522 (4)0.6227 (2)0.0343 (10)
C70.8340 (6)0.6779 (4)0.6146 (2)0.0385 (10)
C80.8896 (6)0.7869 (4)0.6896 (3)0.0429 (11)
C90.0711 (6)0.7066 (4)0.0591 (3)0.0425 (11)
C100.0314 (7)0.7139 (4)0.0255 (3)0.0540 (13)
H100.08870.66160.06810.065*
C110.0892 (8)0.7962 (5)0.0452 (3)0.0666 (15)
H110.11650.79900.10160.080*
C120.1726 (7)0.8765 (5)0.0174 (3)0.0596 (14)
H120.25470.93420.00410.071*
C130.1324 (6)0.8693 (4)0.0977 (3)0.0501 (12)
H130.18940.92200.14020.060*
C140.0180 (6)0.7813 (4)0.2088 (2)0.0450 (11)
H14A0.00830.68990.20940.054*
H14B0.07840.82730.23840.054*
C150.2219 (6)0.8398 (4)0.2576 (2)0.0351 (10)
C160.2595 (6)0.8265 (4)0.3390 (2)0.0414 (11)
H160.16170.78280.36090.050*
C170.4406 (6)0.8774 (4)0.3885 (3)0.0460 (11)
H170.46630.86620.44290.055*
C180.5819 (6)0.9442 (4)0.3567 (3)0.0425 (11)
C190.5470 (6)0.9620 (4)0.2772 (2)0.0437 (11)
H190.64331.00910.25650.052*
C200.3655 (6)0.9086 (4)0.2278 (2)0.0441 (11)
H200.34060.91960.17330.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0314 (3)0.0392 (3)0.0285 (3)0.0027 (2)0.0024 (2)0.0076 (2)
S10.0511 (7)0.0430 (7)0.0322 (6)0.0053 (6)0.0058 (5)0.0096 (5)
S20.0499 (7)0.0403 (7)0.0346 (6)0.0042 (5)0.0024 (5)0.0079 (5)
S30.0432 (7)0.0411 (7)0.0319 (6)0.0015 (5)0.0018 (5)0.0099 (5)
S40.0536 (8)0.0406 (7)0.0338 (6)0.0004 (6)0.0011 (5)0.0097 (5)
Cl10.0507 (8)0.0819 (9)0.0652 (9)0.0080 (7)0.0121 (7)0.0213 (7)
N10.092 (3)0.080 (3)0.037 (2)0.018 (3)0.001 (2)0.019 (2)
N20.095 (3)0.061 (3)0.039 (2)0.012 (2)0.008 (2)0.003 (2)
N30.065 (3)0.064 (3)0.035 (2)0.014 (2)0.003 (2)0.017 (2)
N40.086 (3)0.055 (3)0.042 (2)0.012 (2)0.004 (2)0.003 (2)
N50.046 (2)0.042 (2)0.030 (2)0.0037 (18)0.0020 (17)0.0058 (17)
N60.084 (3)0.060 (3)0.043 (2)0.031 (2)0.014 (2)0.013 (2)
C10.046 (3)0.048 (3)0.040 (3)0.008 (2)0.000 (2)0.004 (2)
C20.036 (3)0.044 (3)0.029 (2)0.005 (2)0.0012 (19)0.008 (2)
C30.029 (2)0.045 (3)0.032 (2)0.003 (2)0.0004 (19)0.000 (2)
C40.049 (3)0.054 (3)0.038 (3)0.006 (2)0.001 (2)0.013 (2)
C50.034 (3)0.037 (2)0.033 (2)0.0066 (19)0.002 (2)0.004 (2)
C60.031 (2)0.041 (3)0.032 (2)0.009 (2)0.0037 (18)0.011 (2)
C70.034 (3)0.046 (3)0.032 (2)0.004 (2)0.0013 (19)0.007 (2)
C80.047 (3)0.045 (3)0.038 (3)0.012 (2)0.004 (2)0.014 (2)
C90.054 (3)0.037 (3)0.037 (3)0.008 (2)0.006 (2)0.010 (2)
C100.078 (4)0.051 (3)0.033 (3)0.014 (3)0.012 (2)0.008 (2)
C110.102 (4)0.059 (3)0.034 (3)0.014 (3)0.009 (3)0.012 (3)
C120.073 (4)0.055 (3)0.046 (3)0.020 (3)0.011 (3)0.010 (3)
C130.049 (3)0.047 (3)0.047 (3)0.013 (2)0.003 (2)0.001 (2)
C140.048 (3)0.057 (3)0.029 (2)0.006 (2)0.006 (2)0.010 (2)
C150.041 (3)0.033 (2)0.031 (2)0.007 (2)0.0059 (19)0.0059 (19)
C160.042 (3)0.044 (3)0.038 (3)0.000 (2)0.005 (2)0.013 (2)
C170.055 (3)0.046 (3)0.039 (3)0.008 (2)0.003 (2)0.016 (2)
C180.041 (3)0.039 (3)0.042 (3)0.006 (2)0.002 (2)0.005 (2)
C190.047 (3)0.041 (3)0.046 (3)0.002 (2)0.012 (2)0.016 (2)
C200.050 (3)0.049 (3)0.033 (2)0.008 (2)0.006 (2)0.012 (2)
Geometric parameters (Å, º) top
Ni1—S22.1352 (13)C6—C71.370 (5)
Ni1—S42.1380 (12)C7—C81.435 (5)
Ni1—S32.1380 (11)C9—C101.406 (5)
Ni1—S12.1430 (11)C10—C111.347 (5)
S1—C21.714 (4)C10—H100.9300
S2—C31.721 (4)C11—C121.381 (6)
S3—C61.697 (4)C11—H110.9300
S4—C71.692 (4)C12—C131.337 (5)
Cl1—C181.734 (4)C12—H120.9300
N1—C11.130 (5)C13—H130.9300
N2—C41.132 (5)C14—C151.514 (5)
N3—C51.132 (4)C14—H14A0.9700
N4—C81.137 (5)C14—H14B0.9700
N5—C91.350 (5)C15—C201.368 (5)
N5—C131.361 (5)C15—C161.376 (5)
N5—C141.477 (4)C16—C171.378 (5)
N6—C91.318 (4)C16—H160.9300
N6—H6A0.8600C17—C181.365 (5)
N6—H6B0.8600C17—H170.9300
C1—C21.439 (5)C18—C191.363 (5)
C2—C31.336 (5)C19—C201.384 (5)
C3—C41.441 (6)C19—H190.9300
C5—C61.436 (5)C20—H200.9300
S2—Ni1—S4177.26 (5)C11—C10—H10119.8
S2—Ni1—S386.74 (5)C9—C10—H10119.8
S4—Ni1—S392.64 (5)C10—C11—C12120.7 (4)
S2—Ni1—S192.68 (5)C10—C11—H11119.6
S4—Ni1—S187.95 (5)C12—C11—H11119.6
S3—Ni1—S1179.41 (5)C13—C12—C11118.3 (4)
C2—S1—Ni1102.58 (14)C13—C12—H12120.8
C3—S2—Ni1103.09 (15)C11—C12—H12120.8
C6—S3—Ni1103.16 (13)C12—C13—N5122.0 (4)
C7—S4—Ni1103.11 (15)C12—C13—H13119.0
C9—N5—C13120.9 (3)N5—C13—H13119.0
C9—N5—C14120.8 (3)N5—C14—C15114.8 (3)
C13—N5—C14118.2 (4)N5—C14—H14A108.6
C9—N6—H6A120.0C15—C14—H14A108.6
C9—N6—H6B120.0N5—C14—H14B108.6
H6A—N6—H6B120.0C15—C14—H14B108.6
N1—C1—C2178.9 (5)H14A—C14—H14B107.5
C3—C2—C1121.8 (4)C20—C15—C16118.6 (4)
C3—C2—S1121.5 (3)C20—C15—C14124.7 (3)
C1—C2—S1116.7 (3)C16—C15—C14116.5 (4)
C2—C3—C4123.5 (4)C15—C16—C17120.7 (4)
C2—C3—S2120.2 (3)C15—C16—H16119.7
C4—C3—S2116.4 (3)C17—C16—H16119.7
N2—C4—C3178.9 (5)C18—C17—C16119.3 (4)
N3—C5—C6179.4 (5)C18—C17—H17120.3
C7—C6—C5121.1 (4)C16—C17—H17120.3
C7—C6—S3120.3 (3)C19—C18—C17121.3 (4)
C5—C6—S3118.5 (3)C19—C18—Cl1119.1 (3)
C6—C7—C8119.6 (3)C17—C18—Cl1119.6 (3)
C6—C7—S4120.8 (3)C18—C19—C20118.6 (4)
C8—C7—S4119.6 (3)C18—C19—H19120.7
N4—C8—C7178.4 (5)C20—C19—H19120.7
N6—C9—N5120.8 (4)C15—C20—C19121.4 (4)
N6—C9—C10121.4 (4)C15—C20—H20119.3
N5—C9—C10117.7 (4)C19—C20—H20119.3
C11—C10—C9120.3 (4)
 

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