Download citation
Download citation
link to html
In the title complex, (C19H42N)[Ni(C3S5)2], the Ni atom is coordinated by four 2-thioxo-1,3-dithiole-4,5-dithiol­ate (dmit) S atoms. The [Ni(dmit)2] monoanion has a planar geometry, with the central Ni atom and the four coordinated S atoms forming an NiS4 square plane. There are S...S inter­molecular contacts in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806008415/om6279sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806008415/om6279Isup2.hkl
Contains datablock I

CCDC reference: 605147

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.052
  • wR factor = 0.155
  • Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT230_ALERT_2_C Hirshfeld Test Diff for C21 - C22 .. 5.32 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - S5 .. 5.15 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S6 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S8 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 C9 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Ni1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.42 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C7 - C8 ... 1.43 Ang. PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C8 - C9 ... 1.43 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 18 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 13 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXTL (Bruker, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Hexadecyltrimethylammonium bis(2-thioxo-1,3-dithiole-4,5-dithiolato-κ2S4,S5)nickel(III) top
Crystal data top
(C19H42N)[Ni(C3S5)2]Z = 2
Mr = 735.91F(000) = 774
Triclinic, P1Dx = 1.401 Mg m3
a = 8.051 (5) ÅMo Kα radiation, λ = 0.71069 Å
b = 12.240 (5) ÅCell parameters from 2878 reflections
c = 18.316 (5) Åθ = 2.6–26.1°
α = 93.426 (5)°µ = 1.17 mm1
β = 99.218 (5)°T = 293 K
γ = 100.494 (5)°Plate, red
V = 1744.5 (14) Å30.56 × 0.27 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
6012 independent reflections
Radiation source: fine-focus sealed tube4270 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 99
Tmin = 0.560, Tmax = 0.892k = 1412
8662 measured reflectionsl = 2118
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0848P)2]
where P = (Fo2 + 2Fc2)/3
6012 reflections(Δ/σ)max = 0.001
334 parametersΔρmax = 0.63 e Å3
0 restraintsΔρmin = 0.44 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
C10.6995 (5)0.8698 (3)0.0285 (2)0.0695 (11)
C20.6603 (5)0.7060 (3)0.0544 (2)0.0558 (9)
C30.7316 (5)0.6680 (3)0.0023 (2)0.0541 (9)
C40.6737 (5)0.2796 (3)0.1862 (2)0.0595 (10)
C50.7598 (5)0.2460 (3)0.1345 (2)0.0559 (9)
C60.7329 (5)0.0860 (3)0.2215 (2)0.0603 (10)
C70.3001 (10)0.7192 (5)0.6261 (4)0.158 (3)
H7A0.25500.75850.66470.237*
H7B0.42300.70860.63550.237*
H7C0.25600.76180.57900.237*
C80.2500 (11)0.6132 (5)0.6247 (4)0.156 (3)
H8A0.29110.57500.67400.187*
H8B0.12570.62770.61780.187*
C90.2982 (8)0.5351 (4)0.5733 (3)0.115 (2)
H9A0.25600.57250.52390.138*
H9B0.42250.52060.57990.138*
C100.2469 (9)0.4276 (5)0.5737 (3)0.121 (2)
H10A0.29350.38880.62240.145*
H10B0.12300.44190.56940.145*
C110.2900 (8)0.3498 (4)0.5194 (3)0.1100 (18)
H11A0.24480.38860.47060.132*
H11B0.41400.33410.52420.132*
C120.2335 (8)0.2412 (5)0.5204 (3)0.1123 (18)
H12A0.11020.25660.51830.135*
H12B0.28400.20050.56820.135*
C130.2702 (8)0.1664 (4)0.4634 (3)0.1087 (18)
H13A0.22070.20760.41560.130*
H13B0.39360.15070.46580.130*
C140.2139 (8)0.0594 (4)0.4633 (3)0.1028 (17)
H14A0.26690.01680.51020.123*
H14B0.09110.07460.46260.123*
C150.2469 (8)0.0126 (4)0.4040 (3)0.1027 (17)
H15A0.19750.03090.35700.123*
H15B0.37000.03000.40590.123*
C160.1849 (7)0.1190 (4)0.4024 (3)0.0920 (15)
H16A0.23430.16290.44930.110*
H16B0.06170.10190.40030.110*
C170.2200 (7)0.1899 (4)0.3421 (3)0.0904 (14)
H17A0.34320.20730.34430.108*
H17B0.17080.14610.29520.108*
C180.1569 (6)0.2962 (4)0.3409 (3)0.0890 (14)
H18A0.19930.33740.38920.107*
H18B0.03280.27820.33530.107*
C190.2003 (7)0.3724 (4)0.2839 (3)0.0902 (14)
H19A0.32430.39160.28970.108*
H19B0.15860.33150.23550.108*
C200.1347 (6)0.4762 (4)0.2838 (3)0.0901 (14)
H20A0.16590.51300.33380.108*
H20B0.01040.45660.27290.108*
C210.1908 (6)0.5589 (3)0.2322 (2)0.0796 (13)
H21A0.31430.58330.24420.096*
H21B0.16280.52350.18180.096*
C220.1082 (6)0.6579 (4)0.2362 (3)0.0832 (13)
H22A0.01400.63310.21880.100*
H22B0.12340.68580.28800.100*
C230.0528 (6)0.8343 (4)0.1999 (3)0.0995 (16)
H23A0.06310.79880.17930.149*
H23B0.08730.89720.17320.149*
H23C0.05940.85910.25120.149*
C240.3470 (5)0.8104 (3)0.2265 (2)0.0795 (12)
H24A0.42470.76000.22340.119*
H24B0.35150.83530.27760.119*
H24C0.37960.87350.19950.119*
C250.1603 (6)0.7180 (3)0.1154 (2)0.0765 (12)
H25A0.23550.66650.11040.115*
H25B0.19440.78240.08980.115*
H25C0.04470.68260.09430.115*
N10.1701 (4)0.7523 (3)0.19390 (16)0.0581 (8)
Ni10.70329 (6)0.47444 (3)0.09273 (2)0.04893 (18)
S10.7014 (2)0.99012 (10)0.06389 (9)0.1119 (5)
S20.62251 (16)0.84072 (8)0.05183 (7)0.0751 (3)
S30.77555 (16)0.76192 (9)0.06764 (6)0.0725 (3)
S40.61629 (14)0.62448 (8)0.12397 (6)0.0649 (3)
S50.77857 (14)0.53725 (7)0.00692 (5)0.0586 (3)
S60.61368 (15)0.40746 (8)0.18825 (6)0.0707 (3)
S70.81108 (15)0.33095 (8)0.06742 (5)0.0674 (3)
S80.63257 (17)0.18651 (10)0.25266 (7)0.0810 (4)
S90.81643 (15)0.11729 (8)0.14245 (6)0.0708 (3)
S100.74829 (17)0.02838 (10)0.26272 (8)0.0876 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.072 (3)0.041 (2)0.095 (3)0.0136 (19)0.006 (2)0.020 (2)
C20.047 (2)0.0329 (18)0.085 (3)0.0081 (15)0.0016 (19)0.0112 (18)
C30.055 (2)0.0353 (18)0.068 (2)0.0050 (16)0.0012 (18)0.0112 (16)
C40.057 (2)0.042 (2)0.077 (3)0.0021 (17)0.010 (2)0.0213 (18)
C50.065 (3)0.0355 (18)0.066 (2)0.0067 (17)0.0101 (19)0.0084 (16)
C60.054 (2)0.044 (2)0.080 (3)0.0014 (17)0.0090 (19)0.0167 (18)
C70.212 (9)0.109 (5)0.162 (6)0.061 (5)0.014 (5)0.046 (5)
C80.250 (9)0.096 (5)0.130 (5)0.038 (5)0.043 (5)0.035 (4)
C90.156 (6)0.085 (4)0.111 (4)0.035 (4)0.023 (4)0.023 (3)
C100.166 (6)0.089 (4)0.121 (4)0.035 (4)0.045 (4)0.035 (3)
C110.147 (5)0.082 (4)0.111 (4)0.036 (3)0.030 (4)0.023 (3)
C120.140 (5)0.099 (4)0.109 (4)0.031 (4)0.039 (4)0.038 (3)
C130.139 (5)0.087 (4)0.107 (4)0.032 (4)0.025 (4)0.023 (3)
C140.123 (5)0.091 (4)0.105 (4)0.032 (3)0.031 (3)0.033 (3)
C150.128 (5)0.089 (4)0.100 (4)0.031 (3)0.027 (3)0.024 (3)
C160.111 (4)0.085 (3)0.087 (3)0.024 (3)0.025 (3)0.028 (3)
C170.102 (4)0.081 (3)0.096 (3)0.024 (3)0.030 (3)0.017 (3)
C180.092 (4)0.088 (3)0.093 (3)0.015 (3)0.028 (3)0.028 (3)
C190.100 (4)0.079 (3)0.100 (3)0.021 (3)0.032 (3)0.026 (3)
C200.085 (4)0.097 (4)0.096 (3)0.022 (3)0.024 (3)0.036 (3)
C210.085 (3)0.064 (3)0.094 (3)0.014 (2)0.025 (3)0.013 (2)
C220.079 (3)0.081 (3)0.087 (3)0.006 (3)0.016 (2)0.018 (2)
C230.084 (4)0.092 (4)0.128 (4)0.033 (3)0.021 (3)0.003 (3)
C240.064 (3)0.080 (3)0.084 (3)0.001 (2)0.002 (2)0.006 (2)
C250.109 (4)0.056 (2)0.058 (2)0.007 (2)0.005 (2)0.0030 (19)
N10.0486 (19)0.062 (2)0.0601 (19)0.0042 (15)0.0069 (14)0.0008 (15)
Ni10.0510 (3)0.0313 (3)0.0631 (3)0.00427 (19)0.0094 (2)0.0067 (2)
S10.1483 (14)0.0600 (7)0.1458 (12)0.0395 (8)0.0414 (10)0.0549 (8)
S20.0860 (8)0.0420 (5)0.1078 (8)0.0259 (5)0.0284 (6)0.0195 (5)
S30.0951 (9)0.0489 (6)0.0786 (7)0.0186 (5)0.0187 (6)0.0230 (5)
S40.0735 (7)0.0441 (5)0.0883 (7)0.0201 (5)0.0338 (6)0.0165 (5)
S50.0786 (7)0.0348 (5)0.0637 (6)0.0119 (4)0.0150 (5)0.0056 (4)
S60.0853 (8)0.0528 (6)0.0888 (7)0.0239 (5)0.0418 (6)0.0199 (5)
S70.1030 (9)0.0404 (5)0.0704 (6)0.0228 (5)0.0356 (6)0.0155 (4)
S80.0966 (9)0.0664 (7)0.0962 (8)0.0231 (6)0.0463 (7)0.0363 (6)
S90.0912 (8)0.0400 (5)0.0895 (7)0.0182 (5)0.0293 (6)0.0187 (5)
S100.0832 (9)0.0600 (7)0.1244 (10)0.0122 (6)0.0204 (7)0.0474 (7)
Geometric parameters (Å, º) top
C1—S11.642 (4)C15—C161.477 (6)
C1—S21.719 (4)C15—H15A0.9700
C1—S31.719 (4)C15—H15B0.9700
C2—C31.362 (5)C16—C171.477 (6)
C2—S41.706 (4)C16—H16A0.9700
C2—S21.733 (3)C16—H16B0.9700
C3—S51.710 (3)C17—C181.481 (6)
C3—S31.742 (3)C17—H17A0.9700
C4—C51.347 (5)C17—H17B0.9700
C4—S61.720 (4)C18—C191.481 (6)
C4—S81.746 (3)C18—H18A0.9700
C5—S71.709 (4)C18—H18B0.9700
C5—S91.726 (3)C19—C201.461 (6)
C6—S101.645 (4)C19—H19A0.9700
C6—S81.708 (4)C19—H19B0.9700
C6—S91.726 (4)C20—C211.487 (5)
C7—C81.428 (7)C20—H20A0.9700
C7—H7A0.9600C20—H20B0.9700
C7—H7B0.9600C21—C221.487 (6)
C7—H7C0.9600C21—H21A0.9700
C8—C91.429 (7)C21—H21B0.9700
C8—H8A0.9700C22—N11.485 (5)
C8—H8B0.9700C22—H22A0.9700
C9—C101.449 (7)C22—H22B0.9700
C9—H9A0.9700C23—N11.509 (5)
C9—H9B0.9700C23—H23A0.9600
C10—C111.455 (7)C23—H23B0.9600
C10—H10A0.9700C23—H23C0.9600
C10—H10B0.9700C24—N11.483 (5)
C11—C121.481 (7)C24—H24A0.9600
C11—H11A0.9700C24—H24B0.9600
C11—H11B0.9700C24—H24C0.9600
C12—C131.461 (6)C25—N11.460 (4)
C12—H12A0.9700C25—H25A0.9600
C12—H12B0.9700C25—H25B0.9600
C13—C141.461 (6)C25—H25C0.9600
C13—H13A0.9700Ni1—S62.1479 (11)
C13—H13B0.9700Ni1—S72.1540 (12)
C14—C151.466 (6)Ni1—S52.1545 (11)
C14—H14A0.9700Ni1—S42.1592 (12)
C14—H14B0.9700
S1—C1—S2122.9 (2)C17—C16—H16B107.7
S1—C1—S3123.4 (3)H16A—C16—H16B107.1
S2—C1—S3113.7 (2)C18—C17—C16117.9 (4)
C3—C2—S4120.8 (3)C18—C17—H17A107.8
C3—C2—S2116.0 (3)C16—C17—H17A107.8
S4—C2—S2123.1 (2)C18—C17—H17B107.8
C2—C3—S5121.5 (3)C16—C17—H17B107.8
C2—C3—S3115.7 (3)H17A—C17—H17B107.2
S5—C3—S3122.8 (2)C17—C18—C19118.9 (4)
C5—C4—S6122.3 (3)C17—C18—H18A107.6
C5—C4—S8115.6 (3)C19—C18—H18A107.6
S6—C4—S8122.2 (2)C17—C18—H18B107.6
C4—C5—S7120.0 (3)C19—C18—H18B107.6
C4—C5—S9116.2 (3)H18A—C18—H18B107.0
S7—C5—S9123.8 (2)C20—C19—C18117.6 (4)
S10—C6—S8123.4 (2)C20—C19—H19A107.9
S10—C6—S9123.7 (2)C18—C19—H19A107.9
S8—C6—S9112.9 (2)C20—C19—H19B107.9
C8—C7—H7A109.5C18—C19—H19B107.9
C8—C7—H7B109.5H19A—C19—H19B107.2
H7A—C7—H7B109.5C19—C20—C21118.5 (4)
C8—C7—H7C109.5C19—C20—H20A107.7
H7A—C7—H7C109.5C21—C20—H20A107.7
H7B—C7—H7C109.5C19—C20—H20B107.7
C7—C8—C9122.7 (7)C21—C20—H20B107.7
C7—C8—H8A106.6H20A—C20—H20B107.1
C9—C8—H8A106.6C22—C21—C20112.3 (4)
C7—C8—H8B106.6C22—C21—H21A109.2
C9—C8—H8B106.6C20—C21—H21A109.2
H8A—C8—H8B106.6C22—C21—H21B109.2
C8—C9—C10121.5 (6)C20—C21—H21B109.2
C8—C9—H9A106.9H21A—C21—H21B107.9
C10—C9—H9A106.9N1—C22—C21117.0 (4)
C8—C9—H9B106.9N1—C22—H22A108.0
C10—C9—H9B106.9C21—C22—H22A108.0
H9A—C9—H9B106.7N1—C22—H22B108.0
C9—C10—C11121.6 (5)C21—C22—H22B108.0
C9—C10—H10A106.9H22A—C22—H22B107.3
C11—C10—H10A106.9N1—C23—H23A109.5
C9—C10—H10B106.9N1—C23—H23B109.5
C11—C10—H10B106.9H23A—C23—H23B109.5
H10A—C10—H10B106.7N1—C23—H23C109.5
C10—C11—C12120.4 (5)H23A—C23—H23C109.5
C10—C11—H11A107.2H23B—C23—H23C109.5
C12—C11—H11A107.2N1—C24—H24A109.5
C10—C11—H11B107.2N1—C24—H24B109.5
C12—C11—H11B107.2H24A—C24—H24B109.5
H11A—C11—H11B106.9N1—C24—H24C109.5
C13—C12—C11119.8 (5)H24A—C24—H24C109.5
C13—C12—H12A107.4H24B—C24—H24C109.5
C11—C12—H12A107.4N1—C25—H25A109.5
C13—C12—H12B107.4N1—C25—H25B109.5
C11—C12—H12B107.4H25A—C25—H25B109.5
H12A—C12—H12B106.9N1—C25—H25C109.5
C12—C13—C14120.3 (5)H25A—C25—H25C109.5
C12—C13—H13A107.2H25B—C25—H25C109.5
C14—C13—H13A107.2C25—N1—C24109.9 (3)
C12—C13—H13B107.2C25—N1—C22112.5 (3)
C14—C13—H13B107.2C24—N1—C22112.0 (3)
H13A—C13—H13B106.9C25—N1—C23108.3 (3)
C13—C14—C15119.4 (5)C24—N1—C23107.7 (3)
C13—C14—H14A107.5C22—N1—C23106.2 (3)
C15—C14—H14A107.5S6—Ni1—S792.90 (4)
C13—C14—H14B107.5S6—Ni1—S5176.61 (5)
C15—C14—H14B107.5S7—Ni1—S587.25 (4)
H14A—C14—H14B107.0S6—Ni1—S487.08 (4)
C14—C15—C16119.5 (5)S7—Ni1—S4175.07 (5)
C14—C15—H15A107.5S5—Ni1—S493.06 (4)
C16—C15—H15A107.5C1—S2—C297.37 (19)
C14—C15—H15B107.5C1—S3—C397.20 (19)
C16—C15—H15B107.5C2—S4—Ni1102.45 (13)
H15A—C15—H15B107.0C3—S5—Ni1102.12 (14)
C15—C16—C17118.3 (4)C4—S6—Ni1101.82 (13)
C15—C16—H16A107.7C5—S7—Ni1103.01 (13)
C17—C16—H16A107.7C6—S8—C497.62 (19)
C15—C16—H16B107.7C6—S9—C597.63 (18)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds