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The crystal structure of the title complex, (C8H10NO2)[Ni(dmit)2] (dmit is 4,5-dimercapto-1,3-di­thiole-2-thione, C3H2S5), is characterized by its two-dimensional S...S intermolecular interactions and can be described as an arrangement of quasi-planar [Ni(dmit)2] anions, separated by cation pairs. Centrosymmetric cation pairs are formed through weak C—H...O hydrogen bonds (H...O = 2.23 Å).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031034/lh6312sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031034/lh6312Isup2.hkl
Contains datablock I

CCDC reference: 262226

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.064
  • wR factor = 0.185
  • Data-to-parameter ratio = 19.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.49 PLAT213_ALERT_2_C Atom C10 has ADP max/min Ratio ............. 3.20 oblate PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (CCDC, 2002); software used to prepare material for publication: SHELXL97, TEXSAN (Molecular Structure Corporation, 2001), KENX (Sakai, 2002), ORTEPIII and Mercury.

3-Methoxycarbonyl-1-methylpyridinium bis(2-thioxo-1,3-dithiole-4,5-dithiolato)nickelate(II) top
Crystal data top
(C8H10NO2)[Ni(C3S5)2]Z = 2
Mr = 603.54F(000) = 610
Triclinic, P1? # Insert any comments here.
Hall symbol: -P 1Dx = 1.847 Mg m3
a = 7.2051 (19) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.139 (3) ÅCell parameters from 2889 reflections
c = 12.732 (3) Åθ = 1.6–27.6°
α = 84.319 (5)°µ = 1.87 mm1
β = 82.170 (5)°T = 100 K
γ = 80.583 (5)°Plate, dark green
V = 1085.0 (5) Å30.19 × 0.12 × 0.02 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4870 independent reflections
Radiation source: fine-focus sealed tube3426 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
Detector resolution: 8.366 pixels mm-1θmax = 27.6°, θmin = 1.6°
ω scansh = 99
Absorption correction: gaussian
(XPREP in SAINT; Bruker, 2001)
k = 1315
Tmin = 0.693, Tmax = 0.967l = 1016
7209 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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0961P)2]
where P = (Fo2 + 2Fc2)/3
4870 reflections(Δ/σ)max = 0.004
255 parametersΔρmax = 1.68 e Å3
0 restraintsΔρmin = 0.67 e Å3
Special details top

Experimental. The first 50 frames were rescanned at the end of data collection to evaluate any possible decay phenomenon. Since it was judged to be negligible, no decay correction was applied to the data.

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.

Mean-plane data from final SHELXL refinement run:-

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

7.1123 (0.0022) x + 1.8207 (0.0054) y - 0.3058 (0.0090) z = 3.3400 (0.0091)

* 0.0090 (0.0015) Ni1 * -0.0162 (0.0017) S6 * -0.0128 (0.0016) S7 * 0.0272 (0.0020) S8 * 0.0164 (0.0019) S9 * -0.0233 (0.0022) S10 * -0.0104 (0.0049) C4 * 0.0050 (0.0047) C5 * 0.0051 (0.0048) C6

Rms deviation of fitted atoms = 0.0157

6.8600 (0.0024) x + 3.2420 (0.0057) y - 1.8108 (0.0088) z = 2.9304 (0.0086)

Angle to previous plane (with approximate e.s.d.) = 10.31 (0.04)

* 0.1290 (0.0015) Ni1 * -0.0252 (0.0016) S1 * -0.0294 (0.0017) S2 * -0.0328 (0.0020) S3 * -0.0277 (0.0020) S4 * 0.0788 (0.0024) S5 * -0.0610 (0.0048) C1 * -0.0584 (0.0049) C2 * 0.0266 (0.0052) C3

Rms deviation of fitted atoms = 0.0615

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
S50.6474 (3)0.04139 (16)0.86499 (16)0.0390 (5)
Ni10.34409 (11)0.61546 (7)0.71595 (6)0.0162 (2)
S10.3720 (2)0.46387 (13)0.63556 (11)0.0173 (3)
S60.3119 (2)0.70143 (13)0.56141 (12)0.0216 (4)
S70.3048 (2)0.76996 (14)0.79397 (12)0.0215 (4)
S20.4032 (2)0.52568 (14)0.86671 (12)0.0221 (4)
S90.2430 (2)1.01230 (13)0.70363 (13)0.0246 (4)
S40.5349 (2)0.27808 (15)0.92125 (13)0.0249 (4)
S30.5045 (2)0.22199 (14)0.70851 (13)0.0236 (4)
S80.2515 (2)0.94934 (13)0.48965 (12)0.0221 (4)
S100.1843 (3)1.19043 (14)0.52853 (14)0.0295 (4)
O10.0299 (7)0.6507 (4)0.0176 (3)0.0262 (10)
C50.2772 (8)0.8698 (5)0.6883 (5)0.0161 (12)
N10.1408 (7)0.4012 (4)0.2470 (4)0.0206 (11)
C10.4404 (8)0.3625 (5)0.7327 (5)0.0171 (12)
O20.0323 (7)0.7798 (4)0.1319 (3)0.0282 (11)
C130.0074 (8)0.6765 (6)0.1032 (5)0.0225 (14)
C20.4546 (8)0.3890 (5)0.8325 (5)0.0196 (13)
C40.2786 (8)0.8393 (5)0.5882 (5)0.0165 (12)
C110.1752 (9)0.4299 (6)0.3405 (5)0.0242 (15)
H110.21910.37430.39070.029*
C120.1747 (10)0.2819 (6)0.2215 (5)0.0285 (15)
H12A0.30810.25840.20330.043*
H12B0.10890.27430.16250.043*
H12C0.12890.23610.28220.043*
C90.0857 (9)0.6232 (6)0.2882 (5)0.0234 (14)
H90.06570.69810.30300.028*
C60.2243 (9)1.0569 (5)0.5713 (5)0.0212 (13)
C140.0817 (11)0.8667 (6)0.0484 (5)0.0338 (17)
H14A0.01340.85890.01220.051*
H14B0.08860.93910.07430.051*
H14C0.20230.85940.02800.051*
C70.0818 (8)0.4821 (6)0.1706 (5)0.0235 (14)
H70.06040.46180.10530.028*
C30.5688 (9)0.1745 (6)0.8342 (5)0.0285 (16)
C80.0545 (8)0.5932 (6)0.1904 (5)0.0208 (13)
C100.1473 (9)0.5393 (5)0.3636 (4)0.0201 (13)
H100.16940.55750.42960.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S50.0537 (12)0.0209 (10)0.0402 (12)0.0003 (8)0.0123 (9)0.0077 (8)
Ni10.0195 (4)0.0143 (4)0.0153 (4)0.0030 (3)0.0023 (3)0.0022 (3)
S10.0240 (8)0.0136 (7)0.0149 (7)0.0025 (6)0.0038 (6)0.0018 (6)
S60.0351 (9)0.0136 (8)0.0168 (8)0.0008 (6)0.0062 (6)0.0043 (6)
S70.0301 (8)0.0199 (8)0.0150 (8)0.0052 (7)0.0018 (6)0.0028 (6)
S20.0268 (8)0.0229 (9)0.0169 (8)0.0035 (6)0.0042 (6)0.0019 (6)
S90.0400 (9)0.0146 (8)0.0197 (8)0.0053 (7)0.0011 (7)0.0054 (6)
S40.0292 (9)0.0249 (9)0.0192 (8)0.0019 (7)0.0049 (6)0.0041 (7)
S30.0323 (9)0.0145 (8)0.0238 (8)0.0027 (6)0.0047 (7)0.0002 (6)
S80.0340 (9)0.0145 (8)0.0172 (8)0.0008 (6)0.0048 (6)0.0034 (6)
S100.0471 (11)0.0142 (8)0.0264 (9)0.0014 (7)0.0058 (8)0.0019 (7)
O10.039 (3)0.023 (3)0.017 (2)0.003 (2)0.0031 (19)0.0044 (19)
C50.017 (3)0.014 (3)0.017 (3)0.004 (2)0.001 (2)0.003 (2)
N10.019 (3)0.015 (3)0.030 (3)0.007 (2)0.001 (2)0.006 (2)
C10.019 (3)0.016 (3)0.016 (3)0.005 (2)0.002 (2)0.001 (2)
O20.045 (3)0.018 (2)0.022 (2)0.007 (2)0.002 (2)0.0036 (19)
C130.018 (3)0.029 (4)0.020 (3)0.004 (3)0.007 (2)0.009 (3)
C20.018 (3)0.023 (3)0.017 (3)0.003 (2)0.003 (2)0.003 (3)
C40.021 (3)0.011 (3)0.016 (3)0.001 (2)0.001 (2)0.002 (2)
C110.021 (3)0.028 (4)0.024 (3)0.007 (3)0.008 (3)0.010 (3)
C120.031 (4)0.026 (4)0.031 (4)0.007 (3)0.011 (3)0.004 (3)
C90.024 (3)0.026 (4)0.022 (3)0.008 (3)0.002 (3)0.009 (3)
C60.024 (3)0.010 (3)0.030 (4)0.004 (2)0.003 (3)0.001 (3)
C140.047 (4)0.027 (4)0.023 (4)0.001 (3)0.004 (3)0.003 (3)
C70.018 (3)0.029 (4)0.025 (3)0.004 (3)0.006 (3)0.003 (3)
C30.027 (3)0.030 (4)0.028 (4)0.007 (3)0.003 (3)0.009 (3)
C80.019 (3)0.027 (4)0.017 (3)0.006 (3)0.001 (2)0.009 (3)
C100.030 (3)0.026 (4)0.007 (3)0.008 (3)0.001 (2)0.009 (2)
Geometric parameters (Å, º) top
S5—C31.650 (7)N1—C71.371 (8)
Ni1—S62.1571 (17)N1—C121.489 (8)
Ni1—S12.1610 (18)C1—C21.363 (8)
Ni1—S72.1686 (19)O2—C131.317 (8)
Ni1—S22.1704 (17)O2—C141.460 (8)
S1—C11.718 (6)C13—C81.489 (9)
S6—C41.714 (6)C11—C101.365 (9)
S7—C51.729 (6)C11—H110.9300
S2—C21.726 (7)C12—H12A0.9600
S9—C51.733 (6)C12—H12B0.9600
S9—C61.734 (6)C12—H12C0.9600
S4—C31.724 (8)C9—C81.388 (8)
S4—C21.745 (6)C9—C101.390 (9)
S3—C11.739 (6)C9—H90.9300
S3—C31.743 (7)C14—H14A0.9600
S8—C61.719 (7)C14—H14B0.9600
S8—C41.745 (6)C14—H14C0.9600
S10—C61.649 (6)C7—C81.374 (9)
O1—C131.203 (7)C7—H70.9300
C5—C41.360 (8)C10—H100.9300
N1—C111.338 (8)
S1···S6i3.667 (2)S3···S9ii3.415 (2)
S3···S6i3.600 (2)S3···S10ii3.553 (2)
S3···S8i3.524 (2)S8···S8iii3.614 (3)
S6—Ni1—S185.30 (7)N1—C11—C10121.4 (6)
S6—Ni1—S793.31 (7)N1—C11—H11119.3
S1—Ni1—S7177.60 (7)C10—C11—H11119.3
S6—Ni1—S2174.91 (7)N1—C12—H12A109.5
S1—Ni1—S293.47 (7)N1—C12—H12B109.5
S7—Ni1—S288.09 (7)H12A—C12—H12B109.5
C1—S1—Ni1102.0 (2)N1—C12—H12C109.5
C4—S6—Ni1102.3 (2)H12A—C12—H12C109.5
C5—S7—Ni1101.9 (2)H12B—C12—H12C109.5
C2—S2—Ni1101.6 (2)C8—C9—C10118.7 (6)
C5—S9—C696.8 (3)C8—C9—H9120.7
C3—S4—C297.0 (3)C10—C9—H9120.7
C1—S3—C396.8 (3)S10—C6—S8123.5 (4)
C6—S8—C497.2 (3)S10—C6—S9122.8 (4)
C4—C5—S7120.9 (5)S8—C6—S9113.7 (3)
C4—C5—S9116.6 (4)O2—C14—H14A109.5
S7—C5—S9122.5 (4)O2—C14—H14B109.5
C11—N1—C7120.2 (6)H14A—C14—H14B109.5
C11—N1—C12121.1 (5)O2—C14—H14C109.5
C7—N1—C12118.6 (5)H14A—C14—H14C109.5
C2—C1—S1121.4 (5)H14B—C14—H14C109.5
C2—C1—S3116.2 (5)N1—C7—C8120.1 (6)
S1—C1—S3122.4 (4)N1—C7—H7119.9
C13—O2—C14114.9 (5)C8—C7—H7119.9
O1—C13—O2125.3 (6)S5—C3—S4124.5 (4)
O1—C13—C8123.0 (6)S5—C3—S3121.8 (5)
O2—C13—C8111.7 (5)S4—C3—S3113.7 (4)
C1—C2—S2121.3 (5)C7—C8—C9119.8 (6)
C1—C2—S4116.3 (5)C7—C8—C13117.1 (6)
S2—C2—S4122.4 (4)C9—C8—C13123.1 (6)
C5—C4—S6121.6 (4)C11—C10—C9119.8 (6)
C5—C4—S8115.6 (4)C11—C10—H10120.1
S6—C4—S8122.7 (4)C9—C10—H10120.1
S6—Ni1—S1—C1170.9 (2)S7—C5—C4—S8179.4 (3)
S2—Ni1—S1—C14.1 (2)S9—C5—C4—S81.6 (6)
S1—Ni1—S6—C4179.0 (2)Ni1—S6—C4—C50.1 (5)
S7—Ni1—S6—C41.0 (2)Ni1—S6—C4—S8177.9 (3)
S6—Ni1—S7—C51.4 (2)C6—S8—C4—C52.2 (5)
S2—Ni1—S7—C5173.7 (2)C6—S8—C4—S6179.7 (4)
S1—Ni1—S2—C24.2 (2)C7—N1—C11—C102.1 (9)
S7—Ni1—S2—C2177.6 (2)C12—N1—C11—C10178.9 (6)
Ni1—S7—C5—C41.8 (5)C4—S8—C6—S10178.0 (4)
Ni1—S7—C5—S9179.2 (3)C4—S8—C6—S92.1 (4)
C6—S9—C5—C40.1 (5)C5—S9—C6—S10178.6 (4)
C6—S9—C5—S7179.1 (4)C5—S9—C6—S81.4 (4)
Ni1—S1—C1—C23.1 (5)C11—N1—C7—C81.2 (9)
Ni1—S1—C1—S3174.2 (3)C12—N1—C7—C8178.1 (5)
C3—S3—C1—C21.3 (5)C2—S4—C3—S5179.8 (4)
C3—S3—C1—S1176.1 (4)C2—S4—C3—S32.1 (4)
C14—O2—C13—O13.3 (9)C1—S3—C3—S5179.8 (4)
C14—O2—C13—C8176.4 (5)C1—S3—C3—S42.1 (4)
S1—C1—C2—S20.4 (7)N1—C7—C8—C90.4 (9)
S3—C1—C2—S2177.9 (3)N1—C7—C8—C13179.3 (5)
S1—C1—C2—S4177.5 (3)C10—C9—C8—C71.0 (9)
S3—C1—C2—S40.0 (6)C10—C9—C8—C13178.6 (5)
Ni1—S2—C2—C13.6 (5)O1—C13—C8—C71.5 (9)
Ni1—S2—C2—S4174.1 (3)O2—C13—C8—C7178.8 (5)
C3—S4—C2—C11.3 (5)O1—C13—C8—C9178.1 (6)
C3—S4—C2—S2176.5 (4)O2—C13—C8—C91.5 (8)
S7—C5—C4—S61.3 (7)N1—C11—C10—C91.4 (9)
S9—C5—C4—S6179.7 (3)C8—C9—C10—C110.2 (9)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y1, z; (iii) x, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O1iv0.932.233.113 (8)158
Symmetry code: (iv) x, y+1, z.
 

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