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The title compound, (C13H13N2O2)[Ni(C3S5)2], is composed of layers of cations and anions. The NiIII ion is in a planar environment, coordinated by the four S atoms of two dmit2− ligands. There are some weak S...S and Ni...S interactions, and some non-classical hydrogen bonds (C—H...S) are also observed. These interactions generate a three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802022006/ob6200sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802022006/ob6200Isup2.hkl
Contains datablock I

CCDC reference: 202966

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.056
  • wR factor = 0.102
  • Data-to-parameter ratio = 14.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








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
(C13H13N2O2)[Ni(C3S5)2]Z = 2
Mr = 680.70F(000) = 690
Triclinic, P1Dx = 1.808 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.982 (1) ÅCell parameters from 885 reflections
b = 12.364 (2) Åθ = 2.2–23.4°
c = 13.978 (2) ŵ = 1.64 mm1
α = 105.43 (1)°T = 293 K
β = 92.45 (1)°Block, black
γ = 108.34 (1)°0.3 × 0.25 × 0.2 mm
V = 1250.1 (3) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
4322 independent reflections
Radiation source: sealed tube2588 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: ψ scan
(SADABS; Bruker, 2000)
h = 79
Tmin = 0.611, Tmax = 0.714k = 1414
6270 measured reflectionsl = 1216
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.102 w = 1/[σ2(Fo2) + (0.02P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
4322 reflectionsΔρmax = 0.47 e Å3
302 parametersΔρmin = 0.32 e Å3
0 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.60 (10)
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
Ni10.52897 (9)0.25431 (6)0.33683 (5)0.0427 (2)
C10.3490 (7)0.0211 (5)0.3805 (4)0.0436 (14)
C20.1901 (7)0.0984 (5)0.4992 (4)0.0501 (15)
C30.3338 (6)0.1043 (5)0.4629 (4)0.0441 (14)
C40.7222 (7)0.4007 (5)0.2079 (4)0.0437 (14)
C50.8959 (7)0.6045 (5)0.1781 (4)0.0486 (15)
C60.7169 (7)0.4849 (5)0.2914 (4)0.0426 (14)
S10.4539 (2)0.06132 (13)0.28558 (10)0.0503 (4)
S20.2602 (2)0.12605 (13)0.38170 (11)0.0546 (4)
S30.0891 (2)0.20400 (15)0.54650 (12)0.0694 (5)
S40.2337 (2)0.05109 (14)0.55649 (11)0.0565 (4)
S50.4099 (2)0.25278 (13)0.47240 (11)0.0536 (4)
S60.62811 (19)0.25232 (13)0.19579 (10)0.0519 (4)
S70.83319 (19)0.45336 (14)0.11630 (10)0.0504 (4)
S81.0164 (2)0.70748 (15)0.13238 (12)0.0682 (5)
S90.8223 (2)0.63313 (13)0.29412 (11)0.0528 (4)
S100.6176 (2)0.44666 (13)0.39030 (10)0.0503 (4)
C70.9103 (7)0.6524 (5)0.7213 (4)0.0480 (15)
H70.98240.72630.71780.058*
C80.8917 (7)0.5533 (5)0.6443 (4)0.0525 (15)
H80.94840.55940.58820.063*
C90.7882 (7)0.4448 (5)0.6508 (4)0.0537 (16)
H90.77530.37570.59980.064*
C100.7038 (7)0.4391 (5)0.7335 (4)0.0525 (16)
H100.63260.36530.73770.063*
C110.7216 (7)0.5386 (5)0.8095 (4)0.0459 (15)
C120.8457 (7)0.7557 (5)0.8845 (4)0.0515 (15)
H12A0.86600.74070.94790.062*
H12B0.73360.77080.88210.062*
C130.9930 (7)0.8669 (5)0.8824 (4)0.0460 (14)
C140.9762 (7)0.9268 (5)0.8149 (4)0.0521 (16)
H140.87220.89870.76980.062*
C151.1106 (8)1.0277 (5)0.8129 (4)0.0540 (16)
H151.10031.06700.76590.065*
C161.2592 (8)1.0685 (5)0.8816 (4)0.0525 (16)
C171.2808 (7)1.0157 (5)0.9533 (4)0.0517 (16)
H171.38211.04731.00080.062*
C181.1437 (7)0.9119 (5)0.9516 (4)0.0479 (15)
H181.15450.87220.99820.058*
C190.6364 (7)0.5339 (5)0.9013 (4)0.0580 (16)
H19A0.72680.56490.95860.087*
H19B0.56770.45270.89570.087*
H19C0.55960.58090.90900.087*
N10.8275 (5)0.6464 (4)0.8022 (3)0.0434 (11)
N21.4052 (9)1.1774 (6)0.8802 (5)0.087
O11.3955 (6)1.2170 (4)0.8104 (4)0.1025 (17)
O21.5303 (7)1.2182 (5)0.9458 (4)0.135 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0477 (5)0.0372 (4)0.0429 (4)0.0124 (3)0.0079 (3)0.0134 (3)
C10.048 (4)0.037 (3)0.045 (3)0.011 (3)0.003 (3)0.014 (3)
C20.056 (4)0.044 (4)0.048 (4)0.009 (3)0.006 (3)0.018 (3)
C30.045 (4)0.040 (4)0.043 (3)0.007 (3)0.004 (3)0.013 (3)
C40.046 (4)0.046 (4)0.041 (3)0.014 (3)0.006 (3)0.018 (3)
C50.049 (4)0.052 (4)0.052 (4)0.019 (3)0.007 (3)0.024 (3)
C60.049 (4)0.041 (4)0.040 (3)0.015 (3)0.006 (3)0.017 (3)
S10.0663 (11)0.0398 (9)0.0456 (9)0.0174 (8)0.0150 (8)0.0134 (7)
S20.0746 (12)0.0387 (9)0.0499 (9)0.0159 (8)0.0147 (8)0.0149 (8)
S30.0906 (13)0.0540 (11)0.0622 (11)0.0127 (9)0.0225 (10)0.0273 (9)
S40.0675 (11)0.0458 (10)0.0510 (10)0.0105 (8)0.0196 (8)0.0141 (8)
S50.0657 (11)0.0383 (9)0.0534 (10)0.0122 (8)0.0214 (8)0.0124 (8)
S60.0658 (11)0.0410 (9)0.0434 (9)0.0132 (8)0.0140 (8)0.0084 (8)
S70.0594 (10)0.0507 (10)0.0408 (9)0.0154 (8)0.0132 (8)0.0157 (8)
S80.0802 (13)0.0603 (12)0.0583 (11)0.0062 (9)0.0152 (9)0.0284 (9)
S90.0720 (11)0.0411 (10)0.0466 (9)0.0166 (8)0.0139 (8)0.0171 (8)
S100.0700 (11)0.0392 (9)0.0450 (9)0.0188 (8)0.0189 (8)0.0156 (7)
C70.052 (4)0.041 (4)0.050 (4)0.011 (3)0.010 (3)0.017 (3)
C80.057 (4)0.044 (4)0.052 (4)0.012 (3)0.009 (3)0.013 (3)
C90.057 (4)0.041 (4)0.057 (4)0.010 (3)0.004 (3)0.015 (3)
C100.051 (4)0.039 (4)0.062 (4)0.004 (3)0.003 (3)0.019 (3)
C110.044 (4)0.040 (4)0.054 (4)0.010 (3)0.003 (3)0.021 (3)
C120.056 (4)0.039 (4)0.054 (4)0.010 (3)0.015 (3)0.010 (3)
C130.050 (4)0.038 (4)0.050 (4)0.016 (3)0.017 (3)0.010 (3)
C140.053 (4)0.044 (4)0.058 (4)0.016 (3)0.009 (3)0.015 (3)
C150.065 (4)0.042 (4)0.057 (4)0.018 (3)0.014 (4)0.017 (3)
C160.059 (4)0.041 (4)0.051 (4)0.013 (3)0.020 (3)0.009 (3)
C170.054 (4)0.050 (4)0.044 (4)0.015 (3)0.011 (3)0.003 (3)
C180.057 (4)0.043 (4)0.044 (3)0.018 (3)0.014 (3)0.011 (3)
C190.059 (4)0.049 (4)0.061 (4)0.005 (3)0.010 (3)0.025 (3)
N10.048 (3)0.036 (3)0.047 (3)0.011 (2)0.009 (2)0.016 (2)
N20.1100.0600.0670.0020.0230.013
O10.109 (4)0.070 (3)0.118 (4)0.001 (3)0.024 (3)0.049 (3)
O20.124 (5)0.124 (5)0.077 (4)0.059 (4)0.007 (3)0.022 (3)
Geometric parameters (Å, º) top
Ni1—S62.1526 (16)C9—H90.9300
Ni1—S52.1577 (16)C10—C111.358 (7)
Ni1—S102.1599 (16)C10—H100.9300
Ni1—S12.1725 (16)C11—N11.368 (6)
C1—C31.363 (6)C11—C191.484 (7)
C1—S11.701 (5)C12—N11.485 (6)
C1—S21.737 (5)C12—C131.510 (7)
C2—S31.623 (6)C12—H12A0.9700
C2—S41.721 (6)C12—H12B0.9700
C2—S21.740 (5)C13—C141.370 (8)
C3—S51.709 (5)C13—C181.373 (7)
C3—S41.732 (5)C14—C151.374 (7)
C4—C61.354 (6)C14—H140.9300
C4—S61.708 (6)C15—C161.361 (7)
C4—S71.739 (5)C15—H150.9300
C5—S81.634 (6)C16—C171.366 (8)
C5—S71.733 (6)C16—N21.483 (8)
C5—S91.735 (5)C17—C181.394 (7)
C6—S101.722 (5)C17—H170.9300
C6—S91.749 (5)C18—H180.9300
C7—N11.341 (6)C19—H19A0.9600
C7—C81.361 (6)C19—H19B0.9600
C7—H70.9300C19—H19C0.9600
C8—C91.366 (7)N2—O21.204 (7)
C8—H80.9300N2—O11.213 (7)
C9—C101.369 (7)
S6—Ni1—S5175.72 (7)C11—C10—H10119.2
S6—Ni1—S1093.35 (6)C9—C10—H10119.2
S5—Ni1—S1087.64 (6)C10—C11—N1118.4 (5)
S6—Ni1—S186.27 (6)C10—C11—C19122.4 (5)
S5—Ni1—S192.95 (6)N1—C11—C19119.1 (5)
S10—Ni1—S1176.97 (7)N1—C12—C13115.5 (4)
C3—C1—S1121.4 (4)N1—C12—H12A108.4
C3—C1—S2115.5 (4)C13—C12—H12A108.4
S1—C1—S2123.2 (3)N1—C12—H12B108.4
S3—C2—S4124.5 (3)C13—C12—H12B108.4
S3—C2—S2122.8 (3)H12A—C12—H12B107.5
S4—C2—S2112.7 (3)C14—C13—C18119.1 (5)
C1—C3—S5121.4 (4)C14—C13—C12121.1 (6)
C1—C3—S4116.4 (4)C18—C13—C12119.7 (6)
S5—C3—S4122.2 (3)C13—C14—C15121.1 (6)
C6—C4—S6121.3 (4)C13—C14—H14119.5
C6—C4—S7116.0 (4)C15—C14—H14119.5
S6—C4—S7122.8 (3)C16—C15—C14118.1 (6)
S8—C5—S7123.1 (3)C16—C15—H15120.9
S8—C5—S9124.2 (3)C14—C15—H15120.9
S7—C5—S9112.6 (3)C15—C16—C17123.6 (6)
C4—C6—S10121.4 (4)C15—C16—N2118.7 (6)
C4—C6—S9116.1 (4)C17—C16—N2117.8 (6)
S10—C6—S9122.5 (3)C16—C17—C18116.7 (6)
C1—S1—Ni1102.06 (19)C16—C17—H17121.6
C1—S2—C297.6 (3)C18—C17—H17121.6
C2—S4—C397.8 (3)C13—C18—C17121.3 (6)
C3—S5—Ni1102.15 (19)C13—C18—H18119.3
C4—S6—Ni1102.34 (19)C17—C18—H18119.3
C5—S7—C497.9 (3)C11—C19—H19A109.5
C5—S9—C697.4 (3)C11—C19—H19B109.5
C6—S10—Ni1101.65 (19)H19A—C19—H19B109.5
N1—C7—C8121.8 (5)C11—C19—H19C109.5
N1—C7—H7119.1H19A—C19—H19C109.5
C8—C7—H7119.1H19B—C19—H19C109.5
C7—C8—C9118.8 (6)C7—N1—C11120.2 (5)
C7—C8—H8120.6C7—N1—C12121.1 (5)
C9—C8—H8120.6C11—N1—C12118.7 (5)
C8—C9—C10119.2 (6)O2—N2—O1123.7 (7)
C8—C9—H9120.4O2—N2—C16118.3 (7)
C10—C9—H9120.4O1—N2—C16117.9 (7)
C11—C10—C9121.6 (6)
 

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