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In the title complex, (C16H36N)2[Ni(C6N2S4)2], the centrosymmetric dianion is flat. The Ni atom has square-planar coordination, with Ni-S bond lengths of 2.1836 (16) and 2.1940 (18) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802004816/ob6113sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802004816/ob6113Isup2.hkl
Contains datablock I

CCDC reference: 183759

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.093
  • wR factor = 0.271
  • Data-to-parameter ratio = 20.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
RFACR_01 Alert C The value of the weighted R factor is > 0.25 Weighted R factor given 0.271 PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(4) - C(6) = 1.43 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku Corporation, 2001); cell refinement: CrystalClear; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku Corporation, 2000); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

bis(tetra-n-butylammonium) bis(2-dicyanomethylene-4,5-dimercapto- 1,3-dithiole)nickel(II) top
Crystal data top
(C16H36N)2[Ni(C6N2S4)2]Z = 1
Mr = 1000.33F(000) = 534
Triclinic, P1Dx = 1.260 Mg m3
Hall symbol: -P 1Melting point: 521 K
a = 8.252 (4) ÅMo Kα radiation, λ = 0.71070 Å
b = 12.012 (6) ÅCell parameters from 4920 reflections
c = 13.867 (6) Åθ = 3.1–27.5°
α = 76.26 (3)°µ = 0.72 mm1
β = 80.99 (3)°T = 173 K
γ = 89.69 (4)°Plate, green–black
V = 1317.9 (10) Å30.60 × 0.20 × 0.05 mm
Data collection top
Rigaku/MSC Mercury CCD
diffractometer
5808 independent reflections
Radiation source: Rigaku rotating anode4177 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
Detector resolution: 14.62 pixels mm-1θmax = 27.5°, θmin = 3.1°
φ and ω scansh = 109
Absorption correction: multi-scan
(Jacobson, 1998)
k = 1415
Tmin = 0.672, Tmax = 0.965l = 1715
12833 measured reflections
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)] = 0.093Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.271H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.1389P)2 + 1.6175P]
where P = (Fo2 + 2Fc2)/3
5808 reflections(Δ/σ)max < 0.001
283 parametersΔρmax = 1.18 e Å3
2 restraintsΔρmin = 0.97 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

7.5493 (0.0056) x + 4.4900 (0.0085) y + 1.0143 (0.0069) z = 5.5125 (0.0065)

* 0.0000 (0.0000) Ni1 * 0.1712 (0.0021) S1 * 0.1160 (0.0018) S2 * 0.1612 (0.0022) S3 * 0.1258 (0.0020) S4 * -0.1493 (0.0044) N1 * -0.0954 (0.0039) N2 * 0.1721 (0.0053) C1 * 0.1594 (0.0047) C2 * 0.0798 (0.0048) C3 * -0.0140 (0.0047) C4 * -0.0856 (0.0050) C5 * -0.0557 (0.0046) C6 * -0.1712 (0.0021) S1_$1 * -0.1160 (0.0018) S2_$1 * -0.1612 (0.0022) S3_$1 * -0.1258 (0.0020) S4_$1 * 0.1493 (0.0044) N1_$1 * 0.0954 (0.0039) N2_$1 * -0.1721 (0.0053) C1_$1 * -0.1594 (0.0047) C2_$1 * -0.0798 (0.0048) C3_$1 * 0.0140 (0.0047) C4_$1 * 0.0856 (0.0050) C5_$1 * 0.0557 (0.0046) C6_$1

Rms deviation of fitted atoms = 0.1202

Operators for generating equivalent atoms: $1 - x + 1, -y + 1, -z - 1

The terminal methyl group (C18A, H18A, H18B, H18C, H17A, H17B and C18B, H18D, H18E, H18F, H17C, H17D) of the tetrabutylammonium cation is disordered over two sites with 0.414 (15) and 0.586 (15) of occupancies, respectively.

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*/UeqOcc. (<1)
Ni10.50000.50000.50000.0387 (3)
S10.41910 (19)0.67241 (12)0.49230 (10)0.0495 (4)
S20.52337 (15)0.45060 (11)0.34088 (10)0.0417 (3)
S30.33232 (19)0.77528 (12)0.31158 (10)0.0475 (4)
S40.42873 (16)0.57436 (11)0.17466 (9)0.0408 (3)
N10.1635 (8)0.9510 (5)0.1395 (5)0.0703 (16)
N20.3226 (6)0.6484 (5)0.0696 (4)0.0594 (13)
N30.0163 (5)0.2592 (4)0.2869 (3)0.0401 (9)
C10.4068 (7)0.6646 (5)0.3650 (4)0.0446 (12)
C20.4522 (6)0.5709 (5)0.3009 (4)0.0398 (11)
C30.3462 (6)0.7062 (5)0.1895 (4)0.0435 (12)
C40.2933 (6)0.7561 (4)0.1087 (4)0.0410 (11)
C50.2220 (7)0.8636 (5)0.1250 (4)0.0486 (13)
C60.3096 (6)0.6967 (5)0.0088 (4)0.0431 (11)
C70.0628 (6)0.3749 (4)0.2997 (4)0.0448 (12)
H7A0.15010.37620.34150.054*
H7B0.11590.38330.23280.054*
C80.0535 (7)0.4767 (5)0.3476 (5)0.0497 (13)
H8A0.10210.47220.41640.060*
H8B0.14380.47510.30800.060*
C90.0363 (7)0.5882 (5)0.3520 (4)0.0512 (13)
H9A0.13410.58490.38460.061*
H9B0.03670.65220.39460.061*
C100.0910 (9)0.6134 (6)0.2493 (6)0.0695 (18)
H10A0.17110.55410.20860.104*
H10B0.14140.68850.25800.104*
H10C0.00440.61390.21530.104*
C110.1575 (6)0.2517 (5)0.2283 (4)0.0437 (12)
H11A0.24990.30110.27090.052*
H11B0.19470.17180.21470.052*
C120.1193 (7)0.2865 (5)0.1294 (4)0.0499 (13)
H12A0.09530.36910.14230.060*
H12B0.02070.24280.08820.060*
C130.2626 (8)0.2639 (6)0.0724 (5)0.0573 (15)
H13A0.36160.30610.11450.069*
H13B0.28490.18100.05840.069*
C140.2286 (10)0.3006 (8)0.0259 (5)0.082 (2)
H14A0.21060.38320.01210.122*
H14B0.32270.28330.06160.122*
H14C0.13040.25900.06760.122*
C150.1110 (6)0.1678 (4)0.2285 (4)0.0438 (12)
H15A0.14880.18440.16210.053*
H15B0.05650.09330.21620.053*
C160.2606 (8)0.1544 (6)0.2757 (6)0.0637 (17)
H16A0.31690.22830.28800.076*
H16B0.22470.13630.34170.076*
C170.3786 (9)0.0638 (7)0.2132 (6)0.082 (2)
H17A0.34810.00730.23490.099*0.414 (15)
H17B0.48690.08430.23330.099*0.414 (15)
H17C0.46730.05690.25210.099*0.586 (15)
H17D0.42910.09060.15350.099*0.586 (15)
C18A0.408 (2)0.0306 (15)0.0977 (8)0.066 (5)0.414 (15)
H18A0.48930.03280.07350.099*0.414 (15)
H18B0.44770.09670.07210.099*0.414 (15)
H18C0.30420.00660.07380.099*0.414 (15)
C18B0.3180 (19)0.0532 (10)0.1769 (13)0.103 (7)0.586 (15)
H18D0.27290.08380.23460.155*0.586 (15)
H18E0.40910.10340.13590.155*0.586 (15)
H18F0.23210.04940.13620.155*0.586 (15)
C190.0797 (7)0.2417 (5)0.3912 (4)0.0490 (13)
H19A0.01130.25420.43100.059*
H19B0.16650.30100.42470.059*
C200.1476 (9)0.1267 (6)0.3937 (5)0.0583 (15)
H20A0.06280.06540.36210.070*
H20B0.24250.11300.35720.070*
C210.2020 (9)0.1288 (6)0.5073 (5)0.0691 (18)
H21A0.10590.14320.54270.083*
H21B0.28420.19200.53820.083*
C220.2746 (13)0.0173 (8)0.5193 (7)0.099 (3)
H22A0.36040.00190.47710.148*
H22B0.32240.02430.58980.148*
H22C0.18850.04340.49870.148*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0354 (5)0.0413 (5)0.0387 (5)0.0001 (4)0.0044 (4)0.0092 (4)
S10.0677 (9)0.0420 (7)0.0380 (7)0.0057 (6)0.0086 (6)0.0078 (5)
S20.0412 (7)0.0455 (7)0.0402 (7)0.0087 (5)0.0092 (5)0.0120 (5)
S30.0630 (9)0.0376 (7)0.0419 (7)0.0073 (6)0.0099 (6)0.0087 (5)
S40.0445 (7)0.0424 (7)0.0365 (7)0.0071 (5)0.0091 (5)0.0100 (5)
N10.083 (4)0.049 (3)0.082 (4)0.016 (3)0.021 (3)0.015 (3)
N20.061 (3)0.069 (4)0.046 (3)0.012 (3)0.006 (2)0.011 (2)
N30.039 (2)0.040 (2)0.041 (2)0.0038 (17)0.0075 (17)0.0068 (18)
C10.048 (3)0.040 (3)0.050 (3)0.004 (2)0.009 (2)0.018 (2)
C20.037 (2)0.051 (3)0.033 (2)0.004 (2)0.0027 (19)0.017 (2)
C30.035 (3)0.048 (3)0.045 (3)0.001 (2)0.004 (2)0.006 (2)
C40.040 (3)0.039 (3)0.044 (3)0.002 (2)0.007 (2)0.009 (2)
C50.052 (3)0.047 (3)0.049 (3)0.005 (2)0.011 (2)0.015 (2)
C60.041 (3)0.048 (3)0.042 (3)0.008 (2)0.000 (2)0.018 (2)
C70.043 (3)0.040 (3)0.048 (3)0.009 (2)0.007 (2)0.005 (2)
C80.041 (3)0.049 (3)0.055 (3)0.003 (2)0.005 (2)0.006 (3)
C90.055 (3)0.045 (3)0.050 (3)0.002 (2)0.009 (3)0.003 (2)
C100.081 (5)0.048 (4)0.079 (5)0.003 (3)0.001 (4)0.022 (3)
C110.038 (3)0.044 (3)0.049 (3)0.005 (2)0.012 (2)0.008 (2)
C120.045 (3)0.053 (3)0.053 (3)0.002 (2)0.012 (2)0.013 (3)
C130.058 (3)0.066 (4)0.052 (3)0.001 (3)0.022 (3)0.012 (3)
C140.073 (5)0.120 (7)0.053 (4)0.019 (4)0.009 (3)0.024 (4)
C150.039 (3)0.041 (3)0.052 (3)0.000 (2)0.009 (2)0.012 (2)
C160.062 (4)0.050 (3)0.081 (5)0.000 (3)0.031 (3)0.006 (3)
C170.057 (4)0.105 (6)0.087 (5)0.025 (4)0.019 (4)0.023 (5)
C18A0.068 (10)0.066 (11)0.054 (9)0.006 (8)0.003 (7)0.002 (7)
C18B0.100 (11)0.077 (10)0.113 (13)0.033 (8)0.037 (10)0.028 (9)
C190.051 (3)0.055 (3)0.039 (3)0.001 (2)0.004 (2)0.008 (2)
C200.072 (4)0.057 (4)0.047 (3)0.013 (3)0.007 (3)0.017 (3)
C210.074 (4)0.063 (4)0.067 (4)0.001 (3)0.004 (3)0.019 (3)
C220.128 (8)0.085 (6)0.088 (6)0.022 (5)0.001 (5)0.044 (5)
Geometric parameters (Å, º) top
Ni1—S12.1940 (18)C12—H12B0.9900
Ni1—S1i2.1940 (18)C13—C141.515 (9)
Ni1—S22.1836 (16)C13—H13A0.9900
Ni1—S2i2.1836 (16)C13—H13B0.9900
S1—C11.732 (6)C14—H14A0.9800
S2—C21.735 (5)C14—H14B0.9800
S3—C31.720 (5)C14—H14C0.9800
S3—C11.735 (5)C15—C161.512 (8)
S4—C31.701 (6)C15—H15A0.9900
S4—C21.742 (5)C15—H15B0.9900
N1—C51.140 (8)C16—C171.478 (10)
N2—C61.125 (7)C16—H16A0.9900
N3—C151.512 (6)C16—H16B0.9900
N3—C111.512 (6)C17—C18B1.487 (9)
N3—C71.516 (7)C17—C18A1.535 (9)
N3—C191.522 (7)C17—H17A0.9900
C1—C21.350 (8)C17—H17B0.9900
C3—C41.403 (8)C17—H17C0.9900
C4—C51.400 (8)C17—H17D0.9900
C4—C61.426 (7)C18A—H18A0.9800
C7—C81.512 (7)C18A—H18B0.9800
C7—H7A0.9900C18A—H18C0.9800
C7—H7B0.9900C18B—H18D0.9800
C8—C91.519 (8)C18B—H18E0.9800
C8—H8A0.9900C18B—H18F0.9800
C8—H8B0.9900C19—C201.494 (8)
C9—C101.526 (9)C19—H19A0.9900
C9—H9A0.9900C19—H19B0.9900
C9—H9B0.9900C20—C211.563 (9)
C10—H10A0.9800C20—H20A0.9900
C10—H10B0.9800C20—H20B0.9900
C10—H10C0.9800C21—C221.498 (11)
C11—C121.514 (8)C21—H21A0.9900
C11—H11A0.9900C21—H21B0.9900
C11—H11B0.9900C22—H22A0.9800
C12—C131.511 (8)C22—H22B0.9800
C12—H12A0.9900C22—H22C0.9800
S2—Ni1—S2i180.0C14—C13—H13A109.3
S2—Ni1—S1i86.71 (6)C12—C13—H13B109.3
S2i—Ni1—S1i93.29 (6)C14—C13—H13B109.3
S2—Ni1—S193.29 (6)H13A—C13—H13B108.0
S2i—Ni1—S186.71 (6)C13—C14—H14A109.5
S1i—Ni1—S1180.0C13—C14—H14B109.5
C1—S1—Ni1101.25 (19)H14A—C14—H14B109.5
C2—S2—Ni1101.39 (18)C13—C14—H14C109.5
C3—S3—C196.2 (3)H14A—C14—H14C109.5
C3—S4—C296.0 (3)H14B—C14—H14C109.5
C15—N3—C11107.5 (4)N3—C15—C16117.1 (5)
C15—N3—C7108.5 (4)N3—C15—H15A108.0
C11—N3—C7112.2 (4)C16—C15—H15A108.0
C15—N3—C19111.7 (4)N3—C15—H15B108.0
C11—N3—C19109.2 (4)C16—C15—H15B108.0
C7—N3—C19107.8 (4)H15A—C15—H15B107.3
C2—C1—S1121.9 (4)C17—C16—C15113.4 (6)
C2—C1—S3115.9 (4)C17—C16—H16A108.9
S1—C1—S3122.3 (3)C15—C16—H16A108.9
C1—C2—S2122.0 (4)C17—C16—H16B108.9
C1—C2—S4116.7 (4)C15—C16—H16B108.9
S2—C2—S4121.3 (3)H16A—C16—H16B107.7
C4—C3—S4122.9 (4)C16—C17—C18B118.7 (8)
C4—C3—S3122.0 (4)C16—C17—C18A124.6 (8)
S4—C3—S3115.1 (3)C16—C17—H17A106.2
C5—C4—C3120.5 (5)C18A—C17—H17A106.2
C5—C4—C6119.4 (5)C16—C17—H17B106.2
C3—C4—C6120.1 (5)C18A—C17—H17B106.2
N1—C5—C4179.1 (6)H17A—C17—H17B106.4
N2—C6—C4179.0 (6)C16—C17—H17C107.6
C8—C7—N3114.9 (4)C18B—C17—H17C107.6
C8—C7—H7A108.5C16—C17—H17D107.6
N3—C7—H7A108.5C18B—C17—H17D107.6
C8—C7—H7B108.5H17C—C17—H17D107.1
N3—C7—H7B108.5C17—C18A—H18A109.5
H7A—C7—H7B107.5C17—C18A—H18B109.5
C7—C8—C9110.6 (4)C17—C18A—H18C109.5
C7—C8—H8A109.5C17—C18B—H18D109.5
C9—C8—H8A109.5C17—C18B—H18E109.5
C7—C8—H8B109.5H18D—C18B—H18E109.5
C9—C8—H8B109.5C17—C18B—H18F109.5
H8A—C8—H8B108.1H18D—C18B—H18F109.5
C8—C9—C10113.8 (5)H18E—C18B—H18F109.5
C8—C9—H9A108.8C20—C19—N3115.4 (4)
C10—C9—H9A108.8C20—C19—H19A108.4
C8—C9—H9B108.8N3—C19—H19A108.4
C10—C9—H9B108.8C20—C19—H19B108.4
H9A—C9—H9B107.7N3—C19—H19B108.4
C9—C10—H10A109.5H19A—C19—H19B107.5
C9—C10—H10B109.5C19—C20—C21106.1 (5)
H10A—C10—H10B109.5C19—C20—H20A110.5
C9—C10—H10C109.5C21—C20—H20A110.5
H10A—C10—H10C109.5C19—C20—H20B110.5
H10B—C10—H10C109.5C21—C20—H20B110.5
N3—C11—C12115.2 (4)H20A—C20—H20B108.7
N3—C11—H11A108.5C22—C21—C20110.9 (7)
C12—C11—H11A108.5C22—C21—H21A109.5
N3—C11—H11B108.5C20—C21—H21A109.5
C12—C11—H11B108.5C22—C21—H21B109.5
H11A—C11—H11B107.5C20—C21—H21B109.5
C13—C12—C11110.6 (5)H21A—C21—H21B108.0
C13—C12—H12A109.5C21—C22—H22A109.5
C11—C12—H12A109.5C21—C22—H22B109.5
C13—C12—H12B109.5H22A—C22—H22B109.5
C11—C12—H12B109.5C21—C22—H22C109.5
H12A—C12—H12B108.1H22A—C22—H22C109.5
C12—C13—C14111.5 (6)H22B—C22—H22C109.5
C12—C13—H13A109.3
S2—Ni1—S1—C14.18 (19)S3—C3—C4—C6178.9 (4)
S2i—Ni1—S1—C1175.82 (19)C15—N3—C7—C8174.0 (4)
S1i—Ni1—S2—C2176.18 (18)C11—N3—C7—C855.3 (6)
S1—Ni1—S2—C23.82 (18)C19—N3—C7—C864.8 (6)
Ni1—S1—C1—C23.9 (5)N3—C7—C8—C9177.1 (4)
Ni1—S1—C1—S3175.0 (3)C7—C8—C9—C1069.0 (7)
C3—S3—C1—C21.9 (5)C15—N3—C11—C1268.2 (6)
C3—S3—C1—S1177.0 (3)C7—N3—C11—C1251.0 (6)
S1—C1—C2—S21.0 (7)C19—N3—C11—C12170.4 (5)
S3—C1—C2—S2178.0 (3)N3—C11—C12—C13174.0 (5)
S1—C1—C2—S4178.7 (3)C11—C12—C13—C14178.7 (6)
S3—C1—C2—S40.3 (6)C11—N3—C15—C16176.6 (5)
Ni1—S2—C2—C12.6 (5)C7—N3—C15—C1661.8 (6)
Ni1—S2—C2—S4175.0 (3)C19—N3—C15—C1656.9 (6)
C3—S4—C2—C11.5 (5)N3—C15—C16—C17179.6 (6)
C3—S4—C2—S2176.2 (3)C15—C16—C17—C18B53.1 (12)
C2—S4—C3—C4177.4 (4)C15—C16—C17—C18A31.7 (13)
C2—S4—C3—S32.8 (3)C15—N3—C19—C2055.2 (6)
C1—S3—C3—C4177.2 (4)C11—N3—C19—C2063.6 (6)
C1—S3—C3—S42.9 (4)C7—N3—C19—C20174.3 (5)
S4—C3—C4—C5178.2 (4)N3—C19—C20—C21179.3 (5)
S3—C3—C4—C52.0 (7)C19—C20—C21—C22179.3 (6)
S4—C3—C4—C60.9 (7)
Symmetry code: (i) x+1, y+1, z1.
 

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