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In the title compound, (C16H13FN)[Ni(C3S5)2], the NiIII ion exhibits square-planar coordination geometry formed by four S atoms from two 2-thioxo-1,3-dithiole-4,5-dithiol­ate (dmit) ligands. π–π inter­actions occur between parallel dmit ligands.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806030613/xu2063sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806030613/xu2063Isup2.hkl
Contains datablock I

CCDC reference: 621537

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.041
  • wR factor = 0.093
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

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Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C16 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C20
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_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 2 ALERT level G = General alerts; check 2 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 0 ALERT type 5 Informative message, check

Computing details top

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.

N-(4-Fluorobenzyl)isoquinolinium bis(2-thioxo-1,3-dithiole-4,5-dithiolato)nickelate(III) top
Crystal data top
(C16H13FN)[Ni(C3S5)2]F(000) = 1396
Mr = 689.64Dx = 1.729 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 833 reflections
a = 9.390 (2) Åθ = 3.2–23.6°
b = 14.959 (4) ŵ = 1.54 mm1
c = 18.911 (5) ÅT = 293 K
β = 94.056 (4)°Needle, black
V = 2649.6 (11) Å30.3 × 0.1 × 0.1 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4651 independent reflections
Radiation source: fine-focus sealed tube3488 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.079
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1110
Tmin = 0.829, Tmax = 0.853k = 1717
12831 measured reflectionsl = 1122
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0332P)2]
where P = (Fo2 + 2Fc2)/3
4651 reflections(Δ/σ)max = 0.001
316 parametersΔρmax = 0.59 e Å3
0 restraintsΔρmin = 0.47 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
Ni10.83508 (4)0.42387 (2)0.01250 (2)0.04720 (14)
C11.0274 (4)0.4009 (2)0.25313 (17)0.0576 (9)
C20.8804 (3)0.43712 (19)0.14364 (16)0.0489 (8)
C30.9906 (3)0.3852 (2)0.11830 (16)0.0515 (8)
C40.6441 (3)0.4169 (2)0.27823 (18)0.0589 (9)
C50.6763 (3)0.44624 (19)0.14439 (17)0.0489 (8)
C60.7904 (3)0.39714 (18)0.16764 (16)0.0461 (7)
C70.3173 (4)0.2720 (2)0.1107 (2)0.0650 (10)
H70.38900.31510.11370.078*
C80.2462 (4)0.2517 (2)0.1712 (2)0.0604 (9)
C90.2798 (5)0.2925 (3)0.2368 (2)0.0948 (14)
H90.35380.33380.24210.114*
C100.2028 (6)0.2712 (3)0.2926 (3)0.1047 (16)
H100.22580.29720.33660.126*
C110.0898 (6)0.2108 (3)0.2847 (3)0.1009 (16)
H110.03670.19800.32310.121*
C120.0572 (5)0.1713 (3)0.2231 (2)0.0815 (12)
H120.01940.13180.21840.098*
C130.1367 (4)0.1884 (2)0.1650 (2)0.0591 (9)
C140.1107 (4)0.1457 (2)0.1002 (2)0.0667 (10)
H140.04110.10150.09530.080*
C150.1847 (4)0.1675 (2)0.0449 (2)0.0654 (9)
H150.16640.13770.00210.078*
C160.3613 (4)0.2545 (2)0.0145 (2)0.0774 (12)
H16A0.38720.31720.01330.093*
H16B0.29740.24440.05630.093*
C170.4935 (3)0.1989 (2)0.01933 (17)0.0525 (8)
C180.4891 (4)0.1180 (2)0.05378 (18)0.0669 (9)
H180.40350.09770.07590.080*
C190.6109 (4)0.0665 (2)0.0558 (2)0.0696 (10)
H190.60860.01230.08000.083*
C200.7331 (4)0.0964 (2)0.0221 (2)0.0597 (9)
C210.7410 (4)0.1760 (2)0.0106 (2)0.0722 (10)
H210.82740.19620.03190.087*
C220.6210 (4)0.2265 (2)0.0124 (2)0.0710 (11)
H220.62590.28120.03570.085*
F10.8520 (2)0.04512 (14)0.02218 (13)0.0882 (7)
N10.2858 (3)0.23217 (18)0.05008 (16)0.0576 (7)
S11.08775 (13)0.39137 (7)0.33146 (5)0.0835 (3)
S20.87729 (10)0.46074 (6)0.23409 (5)0.0633 (3)
S31.10921 (10)0.34974 (6)0.17887 (5)0.0645 (3)
S40.75526 (9)0.47534 (6)0.08984 (4)0.0573 (2)
S51.01321 (9)0.35887 (6)0.03080 (5)0.0627 (3)
S60.58092 (12)0.41383 (8)0.35682 (5)0.0855 (3)
S70.55696 (10)0.47161 (6)0.20745 (5)0.0649 (3)
S80.79856 (9)0.36571 (6)0.25647 (5)0.0600 (2)
S90.65144 (9)0.48185 (5)0.05828 (4)0.0549 (2)
S100.91958 (8)0.36892 (5)0.11213 (4)0.0528 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0500 (3)0.0467 (2)0.0437 (2)0.00355 (19)0.00543 (19)0.00385 (19)
C10.065 (2)0.0569 (19)0.051 (2)0.0070 (17)0.0024 (17)0.0041 (16)
C20.061 (2)0.0469 (17)0.0382 (17)0.0070 (16)0.0023 (16)0.0025 (15)
C30.056 (2)0.0518 (18)0.0458 (19)0.0012 (16)0.0005 (16)0.0048 (16)
C40.058 (2)0.066 (2)0.051 (2)0.0074 (17)0.0028 (17)0.0049 (17)
C50.0548 (19)0.0435 (16)0.0479 (18)0.0024 (15)0.0016 (16)0.0036 (15)
C60.0559 (19)0.0425 (16)0.0388 (17)0.0032 (15)0.0047 (15)0.0036 (14)
C70.051 (2)0.056 (2)0.087 (3)0.0032 (17)0.001 (2)0.004 (2)
C80.058 (2)0.058 (2)0.064 (2)0.0135 (18)0.0022 (19)0.0127 (19)
C90.094 (3)0.095 (3)0.094 (4)0.000 (3)0.004 (3)0.030 (3)
C100.133 (5)0.105 (4)0.076 (3)0.027 (3)0.007 (3)0.028 (3)
C110.120 (4)0.097 (4)0.089 (4)0.042 (3)0.031 (3)0.015 (3)
C120.092 (3)0.068 (2)0.087 (3)0.021 (2)0.021 (3)0.022 (2)
C130.062 (2)0.0450 (18)0.069 (2)0.0150 (17)0.002 (2)0.0085 (18)
C140.067 (2)0.051 (2)0.080 (3)0.0037 (18)0.007 (2)0.005 (2)
C150.073 (2)0.056 (2)0.065 (2)0.0012 (19)0.013 (2)0.0014 (19)
C160.079 (3)0.078 (2)0.076 (3)0.022 (2)0.014 (2)0.031 (2)
C170.062 (2)0.0456 (18)0.050 (2)0.0025 (16)0.0046 (17)0.0120 (16)
C180.065 (2)0.077 (2)0.057 (2)0.009 (2)0.0080 (18)0.005 (2)
C190.084 (3)0.060 (2)0.065 (2)0.002 (2)0.004 (2)0.0144 (19)
C200.061 (2)0.055 (2)0.064 (2)0.0027 (18)0.0104 (19)0.0002 (18)
C210.057 (2)0.069 (2)0.091 (3)0.0081 (19)0.005 (2)0.019 (2)
C220.075 (3)0.0464 (19)0.092 (3)0.0096 (19)0.013 (2)0.013 (2)
F10.0790 (15)0.0820 (14)0.1054 (18)0.0201 (12)0.0193 (14)0.0065 (14)
N10.0585 (18)0.0523 (16)0.0611 (19)0.0148 (14)0.0023 (15)0.0090 (15)
S10.1072 (9)0.0939 (7)0.0506 (6)0.0062 (6)0.0132 (6)0.0014 (6)
S20.0742 (6)0.0699 (5)0.0443 (5)0.0044 (5)0.0064 (4)0.0062 (4)
S30.0701 (6)0.0705 (6)0.0531 (5)0.0122 (5)0.0059 (5)0.0045 (5)
S40.0593 (5)0.0626 (5)0.0484 (5)0.0125 (4)0.0059 (4)0.0063 (4)
S50.0614 (6)0.0778 (6)0.0488 (5)0.0212 (5)0.0020 (4)0.0144 (5)
S60.0854 (7)0.1230 (9)0.0487 (6)0.0280 (7)0.0088 (5)0.0027 (6)
S70.0668 (6)0.0752 (6)0.0520 (5)0.0259 (5)0.0002 (5)0.0020 (5)
S80.0627 (5)0.0714 (6)0.0449 (5)0.0171 (4)0.0025 (4)0.0082 (4)
S90.0619 (5)0.0535 (5)0.0480 (5)0.0168 (4)0.0061 (4)0.0061 (4)
S100.0499 (5)0.0608 (5)0.0468 (5)0.0122 (4)0.0032 (4)0.0059 (4)
Geometric parameters (Å, º) top
Ni1—S42.1668 (10)C10—C111.395 (6)
Ni1—S52.1465 (10)C10—H100.9300
Ni1—S92.1648 (9)C11—C121.322 (6)
Ni1—S102.1550 (10)C11—H110.9300
C1—S11.629 (3)C12—C131.395 (5)
C1—S21.729 (3)C12—H120.9300
C1—S31.731 (3)C13—C141.386 (5)
C2—C31.354 (4)C14—C151.337 (5)
C2—S41.706 (3)C14—H140.9300
C2—S21.745 (3)C15—N11.354 (4)
C3—S51.699 (3)C15—H150.9300
C3—S31.736 (3)C16—N11.492 (4)
C4—S61.639 (3)C16—C171.503 (4)
C4—S81.716 (3)C16—H16A0.9700
C4—S71.725 (3)C16—H16B0.9700
C5—C61.347 (4)C17—C221.364 (5)
C5—S91.714 (3)C17—C181.374 (4)
C5—S71.735 (3)C18—C191.381 (5)
C6—S101.712 (3)C18—H180.9300
C6—S81.741 (3)C19—C201.349 (5)
C7—N11.307 (4)C19—H190.9300
C7—C81.399 (5)C20—C211.341 (5)
C7—H70.9300C20—F11.355 (4)
C8—C91.398 (5)C21—C221.359 (5)
C8—C131.397 (5)C21—H210.9300
C9—C101.360 (6)C22—H220.9300
C9—H90.9300
S5—Ni1—S1084.95 (3)C14—C13—C8118.0 (3)
S5—Ni1—S9176.65 (4)C12—C13—C8119.3 (4)
S10—Ni1—S993.30 (4)C15—C14—C13120.7 (3)
S5—Ni1—S492.86 (4)C15—C14—H14119.7
S10—Ni1—S4177.71 (4)C13—C14—H14119.7
S9—Ni1—S488.85 (4)C14—C15—N1121.2 (4)
S1—C1—S2125.2 (2)C14—C15—H15119.4
S1—C1—S3122.4 (2)N1—C15—H15119.4
S2—C1—S3112.42 (18)N1—C16—C17111.6 (3)
C3—C2—S4121.5 (2)N1—C16—H16A109.3
C3—C2—S2115.0 (2)C17—C16—H16A109.3
S4—C2—S2123.53 (19)N1—C16—H16B109.3
C2—C3—S5121.1 (2)C17—C16—H16B109.3
C2—C3—S3116.8 (2)H16A—C16—H16B108.0
S5—C3—S3122.00 (19)C22—C17—C18118.1 (3)
S6—C4—S8124.8 (2)C22—C17—C16120.6 (3)
S6—C4—S7122.3 (2)C18—C17—C16121.3 (3)
S8—C4—S7112.84 (19)C17—C18—C19120.5 (3)
C6—C5—S9122.1 (2)C17—C18—H18119.8
C6—C5—S7115.6 (2)C19—C18—H18119.8
S9—C5—S7122.27 (18)C20—C19—C18118.7 (3)
C5—C6—S10121.1 (2)C20—C19—H19120.7
C5—C6—S8116.2 (2)C18—C19—H19120.7
S10—C6—S8122.71 (18)C21—C20—C19122.0 (3)
N1—C7—C8121.8 (3)C21—C20—F1118.9 (3)
N1—C7—H7119.1C19—C20—F1119.1 (3)
C8—C7—H7119.1C20—C21—C22119.0 (4)
C9—C8—C13119.4 (4)C20—C21—H21120.5
C9—C8—C7122.7 (4)C22—C21—H21120.5
C13—C8—C7118.0 (3)C21—C22—C17121.6 (3)
C10—C9—C8119.2 (4)C21—C22—H22119.2
C10—C9—H9120.4C17—C22—H22119.2
C8—C9—H9120.4C7—N1—C15120.2 (3)
C9—C10—C11120.7 (5)C7—N1—C16121.6 (3)
C9—C10—H10119.7C15—N1—C16118.2 (3)
C11—C10—H10119.7C1—S2—C298.17 (16)
C12—C11—C10120.8 (5)C1—S3—C397.57 (15)
C12—C11—H11119.6C2—S4—Ni1101.79 (11)
C10—C11—H11119.6C3—S5—Ni1102.68 (11)
C11—C12—C13120.6 (5)C4—S7—C597.79 (15)
C11—C12—H12119.7C4—S8—C697.51 (15)
C13—C12—H12119.7C5—S9—Ni1101.34 (11)
C14—C13—C12122.7 (4)C6—S10—Ni1102.07 (11)
 

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