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In the title compound, (C16H13N2O2)[Ni(C3S5)2], the NiIII ion exhibits a square-planar coordination geometry with four S atoms of the two 2-thioxo-1,3-dithiole-4,5-dithiol­ate (dmit) ligands. Inter­molecular S...S and C—H...O inter­actions are observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026286/bi2024sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026286/bi2024Isup2.hkl
Contains datablock I

CCDC reference: 618123

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.035
  • wR factor = 0.075
  • Data-to-parameter ratio = 14.1

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 PLAT480_ALERT_4_C Long H...A H-Bond Reported H14 .. O2 .. 2.67 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 0 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 1 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
C16H13N2O2·C6NiS10F(000) = 1452
Mr = 716.65Dx = 1.776 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 836 reflections
a = 14.746 (3) Åθ = 2.6–25.8°
b = 9.365 (2) ŵ = 1.53 mm1
c = 19.898 (4) ÅT = 293 K
β = 102.692 (4)°Block, black
V = 2680.6 (10) Å30.3 × 0.2 × 0.1 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
4702 independent reflections
Radiation source: fine-focus sealed tube3776 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
SADABS (Bruker, 2000)
h = 1317
Tmin = 0.70, Tmax = 0.85k = 1110
12871 measured reflectionsl = 2323
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.0331P)2]
where P = (Fo2 + 2Fc2)/3
4702 reflections(Δ/σ)max = 0.009
334 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.21 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
Ni10.89224 (2)0.86912 (4)0.016059 (16)0.03719 (11)
C11.02216 (19)0.7508 (3)0.21410 (13)0.0439 (7)
C20.98426 (18)0.7477 (3)0.09256 (13)0.0396 (7)
C30.93788 (19)0.8618 (3)0.12399 (13)0.0390 (7)
C40.85388 (18)0.8765 (3)0.15854 (13)0.0382 (7)
C50.80575 (18)0.9894 (3)0.12799 (13)0.0377 (7)
C60.78159 (19)0.9895 (3)0.25383 (13)0.0438 (7)
C70.1557 (2)0.5199 (3)0.26195 (15)0.0484 (8)
C80.2021 (2)0.4118 (3)0.23786 (16)0.0549 (8)
H80.21930.33000.26410.066*
C90.2230 (2)0.4263 (3)0.17417 (16)0.0538 (8)
H90.25430.35310.15710.065*
C100.19828 (19)0.5477 (3)0.13514 (14)0.0451 (7)
C110.1500 (2)0.6530 (3)0.16037 (16)0.0528 (8)
H110.13190.73450.13410.063*
C120.1279 (2)0.6400 (3)0.22410 (16)0.0539 (8)
H120.09490.71140.24080.065*
C130.2198 (2)0.5675 (4)0.06501 (15)0.0588 (9)
H13A0.16920.52840.03030.071*
H13B0.22390.66880.05590.071*
C140.3875 (2)0.5420 (3)0.10218 (14)0.0475 (8)
H140.38550.61650.13270.057*
C150.4698 (2)0.4803 (3)0.10118 (13)0.0478 (8)
H150.52360.51120.13130.057*
C160.4741 (2)0.3690 (3)0.05444 (13)0.0421 (7)
C170.5577 (2)0.2994 (3)0.05059 (15)0.0530 (8)
H170.61320.32390.08060.064*
C180.5559 (2)0.1961 (4)0.00241 (16)0.0577 (9)
H180.61100.15050.00020.069*
C190.4739 (3)0.1564 (3)0.04312 (16)0.0589 (9)
H190.47520.08490.07540.071*
C200.3927 (2)0.2205 (3)0.04092 (15)0.0565 (9)
H200.33830.19460.07180.068*
C210.3915 (2)0.3275 (3)0.00885 (13)0.0423 (7)
C220.3089 (2)0.3953 (3)0.01378 (14)0.0502 (8)
H220.25360.36790.01570.060*
N10.1356 (2)0.5065 (4)0.33093 (15)0.0650 (8)
N20.30738 (16)0.4977 (3)0.05940 (11)0.0453 (6)
O10.1020 (2)0.6075 (3)0.35390 (14)0.1062 (10)
O20.15538 (17)0.3932 (3)0.36147 (12)0.0778 (8)
S11.05997 (6)0.71800 (11)0.28352 (4)0.0615 (3)
S21.04863 (6)0.64941 (9)0.13973 (4)0.0513 (2)
S30.95028 (6)0.89433 (9)0.20749 (4)0.0497 (2)
S40.97974 (5)0.70327 (8)0.00984 (3)0.0468 (2)
S50.87028 (6)0.96589 (8)0.08426 (4)0.0490 (2)
S60.91507 (5)0.76800 (8)0.11517 (4)0.0485 (2)
S70.80574 (5)1.03432 (8)0.04431 (4)0.0472 (2)
S80.85283 (6)0.84904 (9)0.24436 (4)0.0491 (2)
S90.74494 (6)1.08580 (9)0.17848 (4)0.0533 (2)
S100.75134 (6)1.02382 (10)0.32650 (4)0.0607 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0409 (2)0.0376 (2)0.0351 (2)0.00272 (16)0.01260 (16)0.00257 (16)
C10.0411 (17)0.0536 (19)0.0375 (16)0.0038 (14)0.0094 (13)0.0040 (14)
C20.0385 (16)0.0446 (18)0.0379 (15)0.0008 (14)0.0133 (13)0.0045 (13)
C30.0412 (17)0.0424 (18)0.0349 (15)0.0035 (13)0.0117 (13)0.0001 (13)
C40.0431 (17)0.0422 (18)0.0310 (14)0.0006 (14)0.0118 (13)0.0004 (13)
C50.0359 (16)0.0446 (18)0.0346 (15)0.0015 (13)0.0123 (13)0.0023 (13)
C60.0427 (17)0.0507 (19)0.0392 (16)0.0060 (14)0.0112 (13)0.0022 (14)
C70.0403 (18)0.054 (2)0.0503 (18)0.0071 (15)0.0094 (15)0.0016 (16)
C80.054 (2)0.049 (2)0.063 (2)0.0035 (16)0.0165 (17)0.0162 (16)
C90.054 (2)0.046 (2)0.066 (2)0.0077 (15)0.0221 (17)0.0046 (16)
C100.0360 (17)0.0478 (19)0.0501 (18)0.0017 (14)0.0068 (14)0.0073 (15)
C110.0500 (19)0.0426 (19)0.063 (2)0.0055 (15)0.0063 (16)0.0099 (16)
C120.050 (2)0.050 (2)0.063 (2)0.0020 (15)0.0132 (16)0.0088 (17)
C130.050 (2)0.069 (2)0.057 (2)0.0093 (17)0.0109 (16)0.0138 (17)
C140.053 (2)0.049 (2)0.0391 (17)0.0037 (16)0.0076 (15)0.0005 (14)
C150.0484 (19)0.056 (2)0.0351 (16)0.0087 (16)0.0010 (14)0.0061 (15)
C160.0485 (18)0.0440 (18)0.0334 (15)0.0045 (15)0.0081 (14)0.0111 (13)
C170.054 (2)0.056 (2)0.0474 (19)0.0007 (17)0.0088 (16)0.0136 (16)
C180.067 (2)0.057 (2)0.053 (2)0.0134 (18)0.0201 (18)0.0150 (17)
C190.086 (3)0.048 (2)0.0466 (19)0.0003 (19)0.0222 (19)0.0058 (15)
C200.070 (2)0.055 (2)0.0438 (18)0.0141 (18)0.0101 (17)0.0022 (16)
C210.0495 (19)0.0418 (18)0.0353 (16)0.0073 (14)0.0088 (14)0.0064 (13)
C220.050 (2)0.059 (2)0.0391 (17)0.0130 (16)0.0040 (14)0.0046 (15)
N10.0557 (19)0.082 (3)0.0582 (19)0.0141 (17)0.0150 (15)0.0003 (18)
N20.0410 (15)0.0543 (17)0.0389 (14)0.0020 (12)0.0053 (12)0.0048 (12)
O10.136 (3)0.117 (3)0.0791 (19)0.019 (2)0.0519 (19)0.0123 (18)
O20.0753 (18)0.096 (2)0.0636 (16)0.0217 (15)0.0188 (13)0.0156 (15)
S10.0637 (6)0.0855 (7)0.0388 (4)0.0061 (5)0.0189 (4)0.0048 (4)
S20.0582 (5)0.0574 (5)0.0409 (4)0.0149 (4)0.0164 (4)0.0001 (4)
S30.0621 (5)0.0520 (5)0.0376 (4)0.0038 (4)0.0168 (4)0.0063 (3)
S40.0579 (5)0.0470 (5)0.0379 (4)0.0148 (4)0.0160 (4)0.0062 (3)
S50.0613 (5)0.0469 (5)0.0426 (4)0.0160 (4)0.0193 (4)0.0098 (4)
S60.0590 (5)0.0488 (5)0.0416 (4)0.0159 (4)0.0194 (4)0.0102 (4)
S70.0566 (5)0.0496 (5)0.0383 (4)0.0151 (4)0.0170 (4)0.0072 (3)
S80.0644 (5)0.0498 (5)0.0359 (4)0.0058 (4)0.0169 (4)0.0056 (3)
S90.0618 (5)0.0617 (6)0.0392 (4)0.0195 (4)0.0172 (4)0.0009 (4)
S100.0756 (6)0.0718 (6)0.0405 (4)0.0082 (5)0.0253 (4)0.0018 (4)
Geometric parameters (Å, º) top
Ni1—S42.1529 (9)C10—C131.509 (4)
Ni1—S52.1509 (9)C11—C121.383 (4)
Ni1—S62.1466 (8)C11—H110.930
Ni1—S72.1567 (9)C12—H120.930
C1—S11.628 (3)C13—N21.474 (4)
C1—S21.729 (3)C13—H13A0.970
C1—S31.735 (3)C13—H13B0.970
C2—C31.347 (4)C14—C151.347 (4)
C2—S41.713 (3)C14—N21.361 (3)
C2—S21.738 (3)C14—H140.930
C3—S51.707 (3)C15—C161.408 (4)
C3—S31.738 (3)C15—H150.930
C4—C51.342 (4)C16—C211.404 (4)
C4—S61.713 (3)C16—C171.411 (4)
C4—S81.730 (3)C17—C181.358 (4)
C5—S71.717 (3)C17—H170.930
C5—S91.739 (3)C18—C191.392 (4)
C6—S101.636 (3)C18—H180.930
C6—S81.719 (3)C19—C201.349 (4)
C6—S91.731 (3)C19—H190.930
C7—C121.366 (4)C20—C211.412 (4)
C7—C81.367 (4)C20—H200.930
C7—N11.472 (4)C21—C221.395 (4)
C8—C91.375 (4)C22—N21.324 (4)
C8—H80.930C22—H220.930
C9—C101.380 (4)N1—O11.203 (4)
C9—H90.930N1—O21.225 (4)
C10—C111.374 (4)
S4—Ni1—S593.31 (3)N2—C13—H13B109.1
S4—Ni1—S685.44 (3)C10—C13—H13B109.1
S4—Ni1—S7178.78 (3)H13A—C13—H13B107.9
S5—Ni1—S6178.66 (3)C15—C14—N2121.4 (3)
S5—Ni1—S787.86 (3)C15—C14—H14119.3
S6—Ni1—S793.40 (3)N2—C14—H14119.3
S1—C1—S2124.58 (18)C14—C15—C16120.0 (3)
S1—C1—S3122.63 (17)C14—C15—H15120.0
S2—C1—S3112.79 (14)C16—C15—H15120.0
C3—C2—S4121.1 (2)C21—C16—C15118.2 (3)
C3—C2—S2116.8 (2)C21—C16—C17118.8 (3)
S4—C2—S2122.11 (17)C15—C16—C17123.0 (3)
C2—C3—S5121.8 (2)C18—C17—C16119.0 (3)
C2—C3—S3115.7 (2)C18—C17—H17120.5
S5—C3—S3122.52 (17)C16—C17—H17120.5
C5—C4—S6121.6 (2)C17—C18—C19122.0 (3)
C5—C4—S8116.5 (2)C17—C18—H18119.0
S6—C4—S8121.93 (16)C19—C18—H18119.0
C4—C5—S7121.3 (2)C20—C19—C18120.6 (3)
C4—C5—S9115.8 (2)C20—C19—H19119.7
S7—C5—S9122.88 (16)C18—C19—H19119.7
S10—C6—S8122.61 (17)C19—C20—C21119.2 (3)
S10—C6—S9124.70 (18)C19—C20—H20120.4
S8—C6—S9112.68 (15)C21—C20—H20120.4
C12—C7—C8122.0 (3)C22—C21—C16118.4 (3)
C12—C7—N1119.2 (3)C22—C21—C20121.2 (3)
C8—C7—N1118.9 (3)C16—C21—C20120.4 (3)
C7—C8—C9118.8 (3)N2—C22—C21121.6 (3)
C7—C8—H8120.6N2—C22—H22119.2
C9—C8—H8120.6C21—C22—H22119.2
C8—C9—C10121.0 (3)O1—N1—O2124.4 (3)
C8—C9—H9119.5O1—N1—C7118.1 (3)
C10—C9—H9119.5O2—N1—C7117.5 (3)
C11—C10—C9118.7 (3)C22—N2—C14120.4 (3)
C11—C10—C13118.7 (3)C22—N2—C13121.4 (3)
C9—C10—C13122.6 (3)C14—N2—C13118.2 (3)
C10—C11—C12121.2 (3)C1—S2—C297.13 (14)
C10—C11—H11119.4C1—S3—C397.54 (13)
C12—C11—H11119.4C2—S4—Ni1101.93 (10)
C7—C12—C11118.4 (3)C3—S5—Ni1101.84 (10)
C7—C12—H12120.8C4—S6—Ni1101.97 (9)
C11—C12—H12120.8C5—S7—Ni1101.71 (10)
N2—C13—C10112.4 (2)C6—S8—C497.62 (13)
N2—C13—H13A109.1C6—S9—C597.33 (13)
C10—C13—H13A109.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O2i0.932.673.456 (4)143
Symmetry code: (i) x+1/2, y+1/2, z+1/2.
 

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