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In the title compound, (C12H11IN)[Ni(C6H4S2)2], the NiIII atom is surrounded by four S atoms in a square-planar geometry. The ions stack in a face-to-face fashion with an alternating arrangement of anion and cation, and a strong S...I inter­action is observed between them.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806024901/hk2070sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806024901/hk2070Isup2.hkl
Contains datablock I

CCDC reference: 618231

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.051
  • wR factor = 0.106
  • Data-to-parameter ratio = 15.1

checkCIF/PLATON results

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Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C19 PLAT431_ALERT_2_C Short Inter HL..A Contact I1 .. S4 .. 3.59 Ang. PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 35.00 A   3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 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: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

1-(4-Iodobenzyl)pyridinium bis(benzene-1,2-dithiolato)nickelate(III) top
Crystal data top
(C12H11IN)[Ni(C6H4S2)2]F(000) = 1260
Mr = 635.25Dx = 1.756 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2936 reflections
a = 16.0187 (18) Åθ = 2.3–25.0°
b = 8.5003 (9) ŵ = 2.45 mm1
c = 17.6621 (19) ÅT = 294 K
β = 92.408 (2)°Block, dark green
V = 2402.8 (5) Å30.15 × 0.10 × 0.10 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4219 independent reflections
Radiation source: sealed tube3526 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
φ and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1619
Tmin = 0.710, Tmax = 0.792k = 1010
11550 measured reflectionsl = 1921
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0253P)2 + 6.1866P]
where P = (Fo2 + 2Fc2)/3
4219 reflections(Δ/σ)max = 0.007
280 parametersΔρmax = 0.91 e Å3
0 restraintsΔρmin = 0.87 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
I11.09318 (3)0.90073 (6)0.23289 (3)0.07630 (19)
Ni10.30851 (4)1.01223 (8)0.47270 (3)0.03890 (18)
S10.20478 (8)0.96412 (17)0.54252 (8)0.0463 (3)
S20.36686 (8)1.16077 (17)0.55757 (7)0.0471 (3)
S30.41862 (8)1.03907 (17)0.40978 (8)0.0471 (3)
S40.24903 (8)0.87281 (17)0.38437 (7)0.0444 (3)
N10.7290 (3)1.0109 (5)0.0047 (3)0.0488 (11)
C10.3257 (3)0.8448 (6)0.3190 (3)0.0399 (11)
C20.3133 (3)0.7432 (6)0.2572 (3)0.0468 (13)
H20.26230.69220.24930.056*
C30.3761 (4)0.7192 (7)0.2087 (3)0.0506 (14)
H30.36760.65170.16770.061*
C40.4521 (4)0.7942 (7)0.2200 (3)0.0533 (14)
H40.49450.77700.18660.064*
C50.4650 (3)0.8937 (6)0.2803 (3)0.0487 (13)
H50.51620.94400.28770.058*
C60.4023 (3)0.9200 (6)0.3303 (3)0.0392 (11)
C70.2972 (3)1.1655 (6)0.6305 (3)0.0416 (12)
C80.3129 (4)1.2568 (7)0.6950 (3)0.0504 (14)
H80.36151.31630.69960.061*
C90.2575 (4)1.2597 (7)0.7512 (3)0.0595 (16)
H90.26821.32120.79400.071*
C100.1845 (4)1.1703 (8)0.7446 (3)0.0641 (17)
H100.14661.17230.78310.077*
C110.1687 (4)1.0803 (7)0.6821 (3)0.0539 (14)
H110.12001.02070.67820.065*
C120.2242 (3)1.0759 (6)0.6239 (3)0.0417 (12)
C131.0042 (3)0.9216 (7)0.1427 (3)0.0497 (14)
C140.9724 (4)0.7921 (7)0.1073 (3)0.0591 (15)
H140.99230.69280.12070.071*
C150.9111 (4)0.8077 (8)0.0520 (4)0.0629 (16)
H150.88940.71830.02800.075*
C160.8807 (3)0.9529 (7)0.0312 (3)0.0497 (14)
C170.9148 (4)1.0836 (7)0.0662 (3)0.0569 (15)
H170.89551.18310.05220.068*
C180.9770 (3)1.0687 (7)0.1216 (3)0.0556 (15)
H181.00041.15770.14460.067*
C190.8105 (4)0.9709 (9)0.0276 (3)0.0674 (18)
H19A0.82521.05270.06290.081*
H19B0.80450.87340.05580.081*
C200.7077 (4)0.9550 (7)0.0716 (3)0.0564 (15)
H200.74480.89010.09880.068*
C210.6328 (4)0.9907 (8)0.1009 (3)0.0605 (16)
H210.61840.95040.14750.073*
C220.5793 (4)1.0870 (8)0.0602 (4)0.0699 (19)
H220.52831.11540.07950.084*
C230.6013 (4)1.1408 (8)0.0087 (4)0.0720 (19)
H230.56471.20460.03720.086*
C240.6760 (4)1.1018 (7)0.0356 (4)0.0594 (16)
H240.69081.13880.08280.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0526 (3)0.0976 (4)0.0777 (3)0.0006 (2)0.0100 (2)0.0119 (3)
Ni10.0380 (3)0.0423 (4)0.0366 (3)0.0022 (3)0.0032 (3)0.0010 (3)
S10.0431 (7)0.0493 (8)0.0468 (8)0.0067 (6)0.0073 (6)0.0032 (6)
S20.0436 (7)0.0552 (9)0.0429 (7)0.0085 (6)0.0061 (6)0.0049 (6)
S30.0446 (7)0.0540 (8)0.0434 (7)0.0131 (6)0.0085 (6)0.0089 (6)
S40.0383 (7)0.0531 (8)0.0416 (7)0.0067 (6)0.0002 (5)0.0010 (6)
N10.045 (3)0.052 (3)0.049 (3)0.007 (2)0.007 (2)0.004 (2)
C10.041 (3)0.039 (3)0.038 (3)0.002 (2)0.002 (2)0.006 (2)
C20.049 (3)0.045 (3)0.045 (3)0.004 (3)0.008 (2)0.001 (2)
C30.066 (4)0.048 (3)0.038 (3)0.004 (3)0.003 (3)0.009 (2)
C40.057 (3)0.054 (4)0.050 (3)0.001 (3)0.013 (3)0.005 (3)
C50.045 (3)0.048 (3)0.053 (3)0.004 (3)0.005 (3)0.003 (3)
C60.045 (3)0.037 (3)0.035 (3)0.003 (2)0.003 (2)0.001 (2)
C70.042 (3)0.040 (3)0.042 (3)0.005 (2)0.001 (2)0.002 (2)
C80.055 (3)0.050 (3)0.046 (3)0.004 (3)0.003 (3)0.004 (3)
C90.077 (4)0.059 (4)0.043 (3)0.009 (3)0.009 (3)0.010 (3)
C100.069 (4)0.071 (4)0.054 (4)0.002 (3)0.026 (3)0.007 (3)
C110.050 (3)0.058 (4)0.054 (4)0.002 (3)0.015 (3)0.001 (3)
C120.048 (3)0.041 (3)0.036 (3)0.006 (2)0.005 (2)0.002 (2)
C130.037 (3)0.058 (4)0.054 (3)0.003 (3)0.004 (2)0.002 (3)
C140.058 (4)0.051 (4)0.068 (4)0.005 (3)0.004 (3)0.001 (3)
C150.066 (4)0.053 (4)0.070 (4)0.007 (3)0.006 (3)0.020 (3)
C160.041 (3)0.063 (4)0.045 (3)0.001 (3)0.008 (2)0.014 (3)
C170.051 (3)0.055 (4)0.064 (4)0.011 (3)0.004 (3)0.009 (3)
C180.046 (3)0.048 (4)0.072 (4)0.002 (3)0.002 (3)0.017 (3)
C190.054 (4)0.099 (5)0.050 (3)0.001 (4)0.005 (3)0.011 (3)
C200.052 (3)0.064 (4)0.052 (4)0.003 (3)0.004 (3)0.005 (3)
C210.055 (4)0.069 (4)0.057 (4)0.018 (3)0.010 (3)0.010 (3)
C220.046 (3)0.067 (4)0.096 (5)0.002 (3)0.005 (4)0.035 (4)
C230.066 (4)0.063 (4)0.085 (5)0.000 (3)0.024 (4)0.003 (4)
C240.059 (4)0.060 (4)0.058 (4)0.008 (3)0.012 (3)0.008 (3)
Geometric parameters (Å, º) top
I1—C132.100 (5)C9—H90.9300
Ni1—S32.1361 (14)C10—C111.359 (8)
Ni1—S22.1441 (15)C10—H100.9300
Ni1—S42.1496 (15)C11—C121.387 (7)
Ni1—S12.1497 (14)C11—H110.9300
S1—C121.740 (5)C13—C141.356 (8)
S2—C71.740 (5)C13—C181.371 (8)
S3—C61.741 (5)C14—C151.361 (8)
S4—C11.738 (5)C14—H140.9300
N1—C201.330 (7)C15—C161.372 (8)
N1—C241.332 (7)C15—H150.9300
N1—C191.488 (7)C16—C171.374 (8)
C1—C61.390 (7)C16—C191.505 (8)
C1—C21.399 (7)C17—C181.372 (8)
C2—C31.364 (7)C17—H170.9300
C2—H20.9300C18—H180.9300
C3—C41.381 (8)C19—H19A0.9700
C3—H30.9300C19—H19B0.9700
C4—C51.368 (7)C20—C211.361 (8)
C4—H40.9300C20—H200.9300
C5—C61.384 (7)C21—C221.367 (9)
C5—H50.9300C21—H210.9300
C7—C81.392 (7)C22—C231.360 (9)
C7—C121.397 (7)C22—H220.9300
C8—C91.359 (7)C23—C241.348 (9)
C8—H80.9300C23—H230.9300
C9—C101.394 (8)C24—H240.9300
S3—Ni1—S287.45 (5)C10—C11—H11119.5
S3—Ni1—S491.83 (5)C12—C11—H11119.5
S2—Ni1—S4177.34 (6)C11—C12—C7118.9 (5)
S3—Ni1—S1173.63 (7)C11—C12—S1121.9 (4)
S2—Ni1—S192.05 (6)C7—C12—S1119.1 (4)
S4—Ni1—S188.95 (5)C14—C13—C18120.4 (5)
C12—S1—Ni1104.75 (18)C14—C13—I1120.8 (4)
C7—S2—Ni1104.90 (18)C18—C13—I1118.8 (4)
C6—S3—Ni1104.93 (18)C15—C14—C13119.9 (6)
C1—S4—Ni1104.69 (18)C15—C14—H14120.1
C20—N1—C24120.1 (5)C13—C14—H14120.1
C20—N1—C19121.4 (5)C14—C15—C16121.2 (6)
C24—N1—C19118.5 (5)C14—C15—H15119.4
C6—C1—C2119.5 (5)C16—C15—H15119.4
C6—C1—S4119.0 (4)C15—C16—C17118.5 (5)
C2—C1—S4121.4 (4)C15—C16—C19121.5 (6)
C3—C2—C1119.8 (5)C17—C16—C19120.0 (6)
C3—C2—H2120.1C18—C17—C16120.6 (6)
C1—C2—H2120.1C18—C17—H17119.7
C2—C3—C4120.6 (5)C16—C17—H17119.7
C2—C3—H3119.7C13—C18—C17119.4 (5)
C4—C3—H3119.7C13—C18—H18120.3
C5—C4—C3120.0 (5)C17—C18—H18120.3
C5—C4—H4120.0N1—C19—C16113.6 (5)
C3—C4—H4120.0N1—C19—H19A108.8
C4—C5—C6120.5 (5)C16—C19—H19A108.8
C4—C5—H5119.8N1—C19—H19B108.8
C6—C5—H5119.8C16—C19—H19B108.8
C5—C6—C1119.5 (5)H19A—C19—H19B107.7
C5—C6—S3121.4 (4)N1—C20—C21121.4 (6)
C1—C6—S3119.0 (4)N1—C20—H20119.3
C8—C7—C12119.6 (5)C21—C20—H20119.3
C8—C7—S2121.3 (4)C20—C21—C22118.5 (6)
C12—C7—S2119.1 (4)C20—C21—H21120.7
C9—C8—C7120.4 (5)C22—C21—H21120.7
C9—C8—H8119.8C23—C22—C21119.4 (6)
C7—C8—H8119.8C23—C22—H22120.3
C8—C9—C10120.0 (5)C21—C22—H22120.3
C8—C9—H9120.0C24—C23—C22120.0 (6)
C10—C9—H9120.0C24—C23—H23120.0
C11—C10—C9120.1 (5)C22—C23—H23120.0
C11—C10—H10120.0N1—C24—C23120.6 (6)
C9—C10—H10120.0N1—C24—H24119.7
C10—C11—C12120.9 (6)C23—C24—H24119.7
S2—Ni1—S1—C122.36 (18)C10—C11—C12—C70.2 (8)
S4—Ni1—S1—C12175.17 (18)C10—C11—C12—S1179.0 (5)
S3—Ni1—S2—C7176.27 (18)C8—C7—C12—C110.0 (8)
S1—Ni1—S2—C72.63 (18)S2—C7—C12—C11179.8 (4)
S2—Ni1—S3—C6176.69 (18)C8—C7—C12—S1179.2 (4)
S4—Ni1—S3—C65.88 (18)S2—C7—C12—S10.6 (6)
S3—Ni1—S4—C15.94 (18)Ni1—S1—C12—C11177.6 (4)
S1—Ni1—S4—C1167.73 (18)Ni1—S1—C12—C71.5 (4)
Ni1—S4—C1—C64.8 (4)C18—C13—C14—C152.0 (9)
Ni1—S4—C1—C2172.4 (4)I1—C13—C14—C15176.0 (4)
C6—C1—C2—C30.2 (8)C13—C14—C15—C160.1 (9)
S4—C1—C2—C3177.4 (4)C14—C15—C16—C171.4 (9)
C1—C2—C3—C40.1 (8)C14—C15—C16—C19177.5 (5)
C2—C3—C4—C50.0 (9)C15—C16—C17—C180.9 (9)
C3—C4—C5—C60.0 (8)C19—C16—C17—C18178.0 (5)
C4—C5—C6—C10.1 (8)C14—C13—C18—C172.5 (9)
C4—C5—C6—S3177.1 (4)I1—C13—C18—C17175.6 (4)
C2—C1—C6—C50.2 (7)C16—C17—C18—C131.0 (9)
S4—C1—C6—C5177.5 (4)C20—N1—C19—C1634.4 (8)
C2—C1—C6—S3177.1 (4)C24—N1—C19—C16147.2 (6)
S4—C1—C6—S30.1 (6)C15—C16—C19—N1104.9 (7)
Ni1—S3—C6—C5172.6 (4)C17—C16—C19—N174.0 (7)
Ni1—S3—C6—C14.6 (4)C24—N1—C20—C211.1 (9)
Ni1—S2—C7—C8177.4 (4)C19—N1—C20—C21179.5 (5)
Ni1—S2—C7—C122.5 (4)N1—C20—C21—C220.4 (9)
C12—C7—C8—C90.2 (8)C20—C21—C22—C231.6 (9)
S2—C7—C8—C9179.6 (4)C21—C22—C23—C241.4 (10)
C7—C8—C9—C100.2 (9)C20—N1—C24—C231.4 (9)
C8—C9—C10—C110.0 (10)C19—N1—C24—C23179.8 (6)
C9—C10—C11—C120.2 (9)C22—C23—C24—N10.1 (10)
 

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