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In the title ion-pair compound, (C12H11FN)[Ni(C3S5)2], the NiIII atom is coordinated by four sulfur atoms of the two 2-thioxo-1,3-dithiole-4,5-dithiol­ate ligands in a square-planar geometry. Weak C—H...S inter­actions are found, resulting in a three-dimensional supra­molecular network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026183/bt2125sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026183/bt2125Isup2.hkl
Contains datablock I

CCDC reference: 618130

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.049
  • wR factor = 0.093
  • Data-to-parameter ratio = 15.4

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 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C13 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT431_ALERT_2_C Short Inter HL..A Contact F1 .. N1 .. 2.88 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 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 5 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

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.

(I) top
Crystal data top
C12H11FN·C6NiS10F(000) = 1292
Mr = 639.67Dx = 1.729 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 237 reflections
a = 8.7766 (17) Åθ = 2.7–23.5°
b = 17.421 (3) ŵ = 1.66 mm1
c = 16.544 (3) ÅT = 293 K
β = 103.774 (4)°Needle, black
V = 2456.8 (8) Å30.3 × 0.1 × 0.1 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
4308 independent reflections
Radiation source: fine-focus sealed tube3041 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
phi and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan
SADABS (Bruker, 2000)
h = 1010
Tmin = 0.818, Tmax = 0.850k = 2020
12038 measured reflectionsl = 1915
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.03P)2]
where P = (Fo2 + 2Fc2)/3
4308 reflections(Δ/σ)max = 0.002
280 parametersΔρmax = 0.54 e Å3
0 restraintsΔρmin = 0.29 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
Ni10.64732 (6)0.04686 (3)0.43035 (3)0.05357 (17)
S10.67351 (15)0.45179 (6)0.38451 (7)0.0805 (4)
S20.80839 (13)0.30651 (6)0.46375 (7)0.0693 (3)
S30.51554 (13)0.30186 (6)0.34085 (7)0.0680 (3)
S40.81510 (13)0.13396 (6)0.48491 (6)0.0645 (3)
S50.49181 (12)0.12852 (6)0.35446 (7)0.0684 (3)
S60.80466 (12)0.03377 (6)0.50658 (6)0.0624 (3)
S70.48456 (12)0.04207 (6)0.37419 (7)0.0655 (3)
S80.78855 (13)0.20626 (6)0.52174 (7)0.0693 (3)
S90.49545 (13)0.21420 (6)0.39881 (7)0.0713 (3)
S100.64536 (17)0.35821 (7)0.47323 (9)0.0995 (5)
F10.9127 (4)0.90146 (19)0.7332 (2)0.1447 (13)
N10.9209 (4)0.54548 (19)0.7386 (2)0.0690 (10)
C10.6665 (5)0.3589 (2)0.3960 (2)0.0629 (11)
C20.7261 (5)0.2160 (2)0.4400 (2)0.0559 (10)
C30.5871 (4)0.2136 (2)0.3826 (2)0.0545 (10)
C50.7121 (4)0.1194 (2)0.4794 (2)0.0538 (10)
C40.6434 (5)0.2646 (2)0.4658 (2)0.0678 (11)
C60.5732 (4)0.1226 (2)0.4210 (2)0.0540 (10)
C121.0983 (6)0.7170 (4)0.7500 (3)0.1043 (19)
H121.18410.69320.73680.125*
C111.0699 (8)0.7935 (4)0.7313 (3)0.110 (2)
H111.13430.82130.70480.132*
C100.9464 (7)0.8272 (3)0.7526 (3)0.0898 (16)
C90.8524 (6)0.7887 (3)0.7920 (3)0.0849 (14)
H90.76970.81360.80720.102*
C80.8798 (6)0.7133 (3)0.8091 (3)0.0797 (13)
H80.81470.68650.83610.096*
C71.0019 (5)0.6754 (3)0.7876 (2)0.0707 (12)
C131.0273 (6)0.5918 (3)0.8033 (3)0.0953 (16)
H13A1.13530.57910.80410.114*
H13B1.00940.57920.85740.114*
C140.9499 (6)0.5405 (3)0.6632 (3)0.0867 (15)
H141.03520.56620.65180.104*
C150.8550 (6)0.4979 (3)0.6033 (3)0.0927 (16)
H150.87690.49360.55120.111*
C160.7316 (6)0.4625 (3)0.6183 (4)0.0895 (15)
H160.66640.43380.57660.107*
C170.7003 (6)0.4679 (3)0.6935 (4)0.0954 (16)
H170.61350.44310.70430.114*
C180.7955 (6)0.5095 (3)0.7533 (3)0.0862 (15)
H180.77390.51340.80560.103*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0399 (3)0.0657 (3)0.0526 (3)0.0022 (2)0.0062 (2)0.0010 (2)
S10.0818 (9)0.0680 (8)0.0850 (9)0.0087 (6)0.0066 (7)0.0040 (6)
S20.0642 (7)0.0662 (7)0.0664 (7)0.0029 (6)0.0067 (6)0.0029 (5)
S30.0542 (7)0.0717 (7)0.0701 (7)0.0116 (6)0.0012 (6)0.0019 (6)
S40.0534 (7)0.0654 (7)0.0627 (6)0.0026 (5)0.0098 (5)0.0021 (5)
S50.0446 (6)0.0742 (7)0.0762 (7)0.0042 (5)0.0058 (5)0.0005 (6)
S60.0496 (6)0.0644 (7)0.0633 (7)0.0027 (5)0.0061 (5)0.0017 (5)
S70.0413 (6)0.0798 (8)0.0684 (7)0.0056 (5)0.0011 (5)0.0032 (6)
S80.0616 (7)0.0630 (7)0.0743 (7)0.0012 (6)0.0015 (6)0.0002 (6)
S90.0566 (7)0.0776 (8)0.0749 (8)0.0170 (6)0.0064 (6)0.0069 (6)
S100.1006 (11)0.0656 (8)0.1274 (11)0.0132 (7)0.0176 (9)0.0027 (8)
F10.153 (3)0.102 (2)0.153 (3)0.057 (2)0.016 (2)0.021 (2)
N10.066 (3)0.080 (3)0.056 (2)0.023 (2)0.004 (2)0.0012 (19)
C10.063 (3)0.069 (3)0.055 (2)0.010 (2)0.010 (2)0.004 (2)
C20.051 (3)0.066 (3)0.050 (2)0.002 (2)0.010 (2)0.0049 (19)
C30.042 (2)0.066 (3)0.054 (2)0.0103 (19)0.0081 (19)0.0005 (19)
C50.044 (2)0.063 (3)0.054 (2)0.0008 (19)0.0107 (19)0.0028 (19)
C40.062 (3)0.071 (3)0.072 (3)0.006 (2)0.019 (2)0.005 (2)
C60.041 (2)0.067 (3)0.053 (2)0.0061 (19)0.0101 (19)0.0034 (19)
C120.068 (4)0.147 (5)0.101 (4)0.033 (4)0.028 (3)0.059 (4)
C110.106 (5)0.139 (6)0.093 (4)0.072 (5)0.041 (4)0.039 (4)
C100.084 (4)0.089 (4)0.082 (4)0.036 (3)0.006 (3)0.002 (3)
C90.062 (3)0.093 (4)0.096 (4)0.004 (3)0.011 (3)0.006 (3)
C80.077 (3)0.093 (4)0.074 (3)0.011 (3)0.027 (3)0.017 (3)
C70.050 (3)0.105 (4)0.049 (3)0.001 (3)0.004 (2)0.012 (2)
C130.081 (4)0.115 (4)0.069 (3)0.025 (3)0.021 (3)0.019 (3)
C140.079 (4)0.117 (4)0.064 (3)0.019 (3)0.018 (3)0.005 (3)
C150.105 (5)0.110 (4)0.062 (3)0.025 (4)0.016 (3)0.004 (3)
C160.074 (4)0.094 (4)0.090 (4)0.002 (3)0.001 (3)0.007 (3)
C170.061 (3)0.097 (4)0.130 (5)0.003 (3)0.026 (4)0.020 (4)
C180.080 (4)0.109 (4)0.081 (4)0.023 (3)0.041 (3)0.017 (3)
Geometric parameters (Å, º) top
Ni1—S62.1544 (11)C5—C61.364 (5)
Ni1—S52.1556 (12)C12—C71.371 (6)
Ni1—S42.1569 (12)C12—C111.376 (7)
Ni1—S72.1615 (12)C12—H120.9300
S1—C11.633 (4)C11—C101.351 (7)
S2—C11.725 (4)C11—H110.9300
S2—C21.739 (4)C10—C91.347 (6)
S3—C11.732 (4)C9—C81.354 (6)
S3—C31.740 (4)C9—H90.9300
S4—C21.712 (4)C8—C71.376 (6)
S5—C31.711 (4)C8—H80.9300
S6—C51.707 (4)C7—C131.487 (6)
S7—C61.700 (4)C13—H13A0.9700
S8—C41.718 (4)C13—H13B0.9700
S8—C51.733 (4)C14—C151.354 (6)
S9—C41.732 (4)C14—H140.9300
S9—C61.739 (4)C15—C161.320 (6)
S10—C41.636 (4)C15—H150.9300
F1—C101.348 (6)C16—C171.340 (7)
N1—C141.333 (5)C16—H160.9300
N1—C181.338 (6)C17—C181.345 (7)
N1—C131.482 (5)C17—H170.9300
C2—C31.357 (5)C18—H180.9300
S6—Ni1—S5179.37 (5)C11—C12—H12119.5
S6—Ni1—S486.28 (4)C10—C11—C12118.4 (5)
S5—Ni1—S493.10 (4)C10—C11—H11120.8
S6—Ni1—S792.87 (4)C12—C11—H11120.8
S5—Ni1—S787.75 (5)C9—C10—F1117.9 (6)
S4—Ni1—S7178.28 (5)C9—C10—C11122.1 (6)
C1—S2—C297.79 (19)F1—C10—C11120.0 (6)
C1—S3—C397.99 (18)C10—C9—C8119.1 (5)
C2—S4—Ni1102.15 (14)C10—C9—H9120.5
C3—S5—Ni1102.28 (13)C8—C9—H9120.5
C5—S6—Ni1102.55 (13)C9—C8—C7121.5 (5)
C6—S7—Ni1102.24 (13)C9—C8—H8119.3
C4—S8—C597.60 (19)C7—C8—H8119.3
C4—S9—C697.64 (19)C12—C7—C8117.8 (5)
C14—N1—C18119.3 (4)C12—C7—C13121.0 (5)
C14—N1—C13118.9 (4)C8—C7—C13121.2 (5)
C18—N1—C13121.8 (4)N1—C13—C7111.4 (3)
S1—C1—S2124.0 (2)N1—C13—H13A109.4
S1—C1—S3123.5 (2)C7—C13—H13A109.4
S2—C1—S3112.5 (2)N1—C13—H13B109.4
C3—C2—S4121.3 (3)C7—C13—H13B109.4
C3—C2—S2116.3 (3)H13A—C13—H13B108.0
S4—C2—S2122.5 (2)N1—C14—C15119.9 (5)
C2—C3—S5121.2 (3)N1—C14—H14120.0
C2—C3—S3115.4 (3)C15—C14—H14120.0
S5—C3—S3123.4 (2)C16—C15—C14120.5 (5)
C6—C5—S6120.7 (3)C16—C15—H15119.7
C6—C5—S8116.4 (3)C14—C15—H15119.7
S6—C5—S8122.8 (2)C15—C16—C17120.0 (5)
S10—C4—S8123.8 (3)C15—C16—H16120.0
S10—C4—S9123.1 (3)C17—C16—H16120.0
S8—C4—S9113.1 (2)C16—C17—C18119.5 (5)
C5—C6—S7121.6 (3)C16—C17—H17120.2
C5—C6—S9115.3 (3)C18—C17—H17120.2
S7—C6—S9123.2 (2)N1—C18—C17120.7 (5)
C7—C12—C11121.0 (5)N1—C18—H18119.6
C7—C12—H12119.5C17—C18—H18119.6
 

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