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In the mol­ecule of the title complex, [Ni(C21H17N3O2S2)], the Ni atom is coordinated by three N atoms and one S atom of the pyridine-2,6-dicarbox­amide ligand. The geometry around the NiII atom is approximately square planar. The crystal structure is stabilized by weak π–π and C—H...O intermolecular interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804017143/cf6369sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804017143/cf6369Isup2.hkl
Contains datablock I

CCDC reference: 248745

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.052
  • wR factor = 0.132
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

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Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H11 .. O2 .. 2.77 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 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 and BERCURY (Version 1.2.1; Bruno et al., 2002); software used to prepare material for publication: SHELXTL.

[N,N'-Bis[2-(methylsulfanyl)phenyl]pyridine-2,6-dicarboxamidato(2-)]nickel(II) top
Crystal data top
[Ni(C21H17N3O2S2)]F(000) = 960
Mr = 466.21Dx = 1.585 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 775 reflections
a = 11.430 (2) Åθ = 2.5–25.0°
b = 11.406 (2) ŵ = 1.23 mm1
c = 15.087 (3) ÅT = 293 K
β = 96.765 (4)°Prism, red
V = 1953.2 (6) Å30.32 × 0.22 × 0.2 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3834 independent reflections
Radiation source: sealed tube3039 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.066
φ and ω scansθmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 814
Tmin = 0.669, Tmax = 0.782k = 1413
10243 measured reflectionsl = 1818
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) = 0.132H-atom parameters constrained
S = 0.92 w = 1/(σ2(Fo2) + (0.07P)2 + 1.55P)
where P = (Fo2 + 2Fc2)/3
3834 reflections(Δ/σ)max < 0.001
264 parametersΔρmax = 0.87 e Å3
0 restraintsΔρmin = 0.83 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.

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

7.9201 (0.0134) x + 8.0106 (0.0134) y + 1.2127 (0.0248) z = 9.1849 (0.0082)

* 0.0166 (0.0026) C14 * -0.0038 (0.0030) C15 * -0.0118 (0.0031) C16 * 0.0142 (0.0029) C17 * -0.0012 (0.0028) C18 * -0.0141 (0.0026) C19

Rms deviation of fitted atoms = 0.0118

- 5.8842 (0.0096) x + 8.8068 (0.0052) y + 6.4968 (0.0137) z = 7.0805 (0.0047)

Angle to previous plane (with approximate e.s.d.) = 75.74 (0.08)

* 0.0003 (0.0011) Ni1 * -0.0259 (0.0015) N1 * 0.0290 (0.0015) N2 * -0.0232 (0.0013) N3 * 0.0199 (0.0010) S1

Rms deviation of fitted atoms = 0.0221

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.11727 (4)0.85609 (4)0.03563 (3)0.03901 (17)
N10.0004 (3)0.8463 (2)0.06099 (19)0.0404 (7)
N20.1857 (3)0.9577 (2)0.03580 (18)0.0359 (6)
N30.2529 (3)0.8853 (3)0.11524 (19)0.0414 (7)
O10.0412 (3)0.9124 (3)0.20783 (17)0.0555 (7)
O20.4225 (2)0.9980 (2)0.12774 (17)0.0563 (7)
S10.01872 (8)0.73777 (8)0.10977 (6)0.0417 (2)
S20.42799 (11)0.69498 (11)0.12325 (7)0.0619 (3)
C10.1000 (3)0.7145 (3)0.0249 (2)0.0435 (9)
C20.1937 (4)0.6428 (4)0.0397 (3)0.0592 (11)
H20.19350.60420.09400.071*
C30.2864 (4)0.6286 (4)0.0257 (3)0.0679 (13)
H30.34860.57920.01670.082*
C40.2865 (4)0.6881 (4)0.1045 (3)0.0658 (12)
H40.35030.67950.14820.079*
C50.1944 (4)0.7606 (4)0.1211 (3)0.0545 (10)
H50.19670.79970.17540.065*
C60.0981 (3)0.7748 (3)0.0559 (2)0.0424 (8)
C70.0188 (3)0.9089 (3)0.1355 (2)0.0431 (9)
C80.1307 (3)0.9774 (3)0.1170 (2)0.0411 (8)
C90.1812 (4)1.0539 (3)0.1727 (2)0.0517 (10)
H90.14411.07090.22940.062*
C100.2878 (4)1.1040 (4)0.1420 (3)0.0537 (10)
H100.32361.15430.17910.064*
C110.3425 (4)1.0811 (3)0.0575 (3)0.0479 (9)
H110.41411.11590.03670.057*
C120.2877 (3)1.0050 (3)0.0052 (2)0.0406 (8)
C130.3296 (3)0.9637 (3)0.0877 (2)0.0429 (9)
C140.2836 (3)0.8375 (3)0.2034 (2)0.0418 (9)
C150.2283 (4)0.8791 (4)0.2732 (3)0.0534 (10)
H150.17060.93660.26310.064*
C160.2585 (4)0.8353 (4)0.3586 (3)0.0584 (11)
H160.22060.86270.40580.070*
C170.3445 (4)0.7513 (4)0.3730 (3)0.0542 (10)
H170.36680.72410.43070.065*
C180.3979 (4)0.7070 (3)0.3038 (3)0.0492 (10)
H180.45480.64890.31450.059*
C190.3673 (3)0.7488 (3)0.2171 (2)0.0414 (8)
C200.5131 (5)0.5733 (5)0.1658 (3)0.0796 (15)
H20A0.57910.60040.20580.119*
H20B0.54100.53120.11730.119*
H20C0.46530.52240.19730.119*
C210.0950 (4)0.5991 (4)0.1111 (3)0.0636 (12)
H21A0.04670.53900.13260.095*
H21B0.16780.60450.14980.095*
H21C0.11110.58000.05180.095*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0459 (3)0.0394 (3)0.0304 (3)0.0006 (2)0.0012 (2)0.00257 (18)
N10.0412 (17)0.0438 (17)0.0344 (16)0.0001 (14)0.0028 (13)0.0005 (13)
N20.0427 (17)0.0354 (15)0.0290 (14)0.0026 (13)0.0016 (12)0.0018 (12)
N30.0460 (18)0.0411 (16)0.0342 (16)0.0000 (14)0.0071 (13)0.0071 (13)
O10.0620 (18)0.0656 (18)0.0354 (14)0.0029 (15)0.0089 (13)0.0030 (13)
O20.0550 (17)0.0612 (18)0.0487 (15)0.0139 (15)0.0107 (14)0.0020 (13)
S10.0457 (5)0.0422 (5)0.0372 (5)0.0018 (4)0.0044 (4)0.0030 (4)
S20.0750 (8)0.0668 (7)0.0452 (6)0.0185 (6)0.0128 (6)0.0093 (5)
C10.043 (2)0.043 (2)0.045 (2)0.0007 (17)0.0041 (17)0.0062 (16)
C20.060 (3)0.058 (3)0.061 (3)0.009 (2)0.012 (2)0.005 (2)
C30.055 (3)0.076 (3)0.074 (3)0.021 (2)0.011 (3)0.015 (3)
C40.051 (3)0.078 (3)0.066 (3)0.011 (2)0.001 (2)0.023 (3)
C50.048 (2)0.062 (3)0.050 (2)0.000 (2)0.0043 (19)0.009 (2)
C60.042 (2)0.042 (2)0.0419 (19)0.0027 (17)0.0003 (16)0.0097 (16)
C70.050 (2)0.045 (2)0.0336 (19)0.0099 (17)0.0011 (17)0.0013 (16)
C80.053 (2)0.0378 (19)0.0318 (17)0.0063 (17)0.0035 (16)0.0001 (15)
C90.071 (3)0.049 (2)0.0339 (19)0.003 (2)0.0003 (19)0.0048 (17)
C100.069 (3)0.048 (2)0.045 (2)0.008 (2)0.011 (2)0.0068 (18)
C110.056 (2)0.042 (2)0.046 (2)0.0046 (19)0.0067 (19)0.0008 (17)
C120.047 (2)0.0362 (18)0.0381 (18)0.0015 (17)0.0023 (16)0.0036 (15)
C130.049 (2)0.0387 (19)0.0395 (19)0.0009 (17)0.0008 (17)0.0039 (16)
C140.045 (2)0.044 (2)0.0341 (18)0.0071 (17)0.0073 (16)0.0025 (15)
C150.064 (3)0.051 (2)0.044 (2)0.004 (2)0.002 (2)0.0021 (18)
C160.079 (3)0.059 (3)0.038 (2)0.003 (2)0.009 (2)0.0007 (18)
C170.072 (3)0.054 (2)0.0338 (19)0.011 (2)0.0059 (19)0.0079 (18)
C180.052 (2)0.048 (2)0.045 (2)0.0008 (19)0.0043 (18)0.0076 (18)
C190.045 (2)0.045 (2)0.0331 (18)0.0061 (17)0.0024 (16)0.0018 (16)
C200.100 (4)0.074 (3)0.066 (3)0.033 (3)0.014 (3)0.002 (3)
C210.067 (3)0.053 (3)0.069 (3)0.008 (2)0.001 (2)0.014 (2)
Geometric parameters (Å, º) top
Ni1—N21.821 (3)C7—C81.497 (5)
Ni1—N11.861 (3)C8—C91.383 (5)
Ni1—N31.876 (3)C9—C101.375 (6)
Ni1—S12.1535 (10)C9—H90.930
N1—C71.369 (5)C10—C111.377 (5)
N1—C61.399 (5)C10—H100.930
N2—C121.318 (5)C11—C121.374 (5)
N2—C81.329 (4)C11—H110.930
N3—C131.351 (5)C12—C131.502 (5)
N3—C141.442 (4)C14—C151.375 (6)
O1—C71.220 (4)C14—C191.391 (5)
O2—C131.223 (4)C15—C161.388 (6)
S1—C11.772 (4)C15—H150.930
S1—C211.805 (4)C16—C171.372 (6)
S2—C191.759 (4)C16—H160.930
S2—C201.771 (5)C17—C181.366 (6)
C1—C21.386 (6)C17—H170.930
C1—C61.402 (5)C18—C191.398 (5)
C2—C31.371 (6)C18—H180.930
C2—H20.930C20—H20A0.960
C3—C41.367 (7)C20—H20B0.960
C3—H30.930C20—H20C0.960
C4—C51.385 (6)C21—H21A0.960
C4—H40.930C21—H21B0.960
C5—C61.397 (5)C21—H21C0.960
C5—H50.930
N2—Ni1—N183.88 (13)C10—C9—H9120.9
N2—Ni1—N383.42 (13)C8—C9—H9120.9
N1—Ni1—N3167.19 (13)C9—C10—C11121.4 (4)
N2—Ni1—S1173.58 (10)C9—C10—H10119.3
N1—Ni1—S189.88 (10)C11—C10—H10119.3
N3—Ni1—S1102.85 (10)C12—C11—C10117.6 (4)
C7—N1—C6123.5 (3)C12—C11—H11121.2
C7—N1—Ni1116.5 (3)C10—C11—H11121.2
C6—N1—Ni1120.0 (2)N2—C12—C11120.1 (3)
C12—N2—C8123.8 (3)N2—C12—C13111.8 (3)
C12—N2—Ni1118.5 (2)C11—C12—C13128.1 (4)
C8—N2—Ni1117.7 (3)O2—C13—N3128.0 (3)
C13—N3—C14116.0 (3)O2—C13—C12121.6 (3)
C13—N3—Ni1115.9 (2)N3—C13—C12110.3 (3)
C14—N3—Ni1128.0 (2)C15—C14—C19120.5 (3)
C1—S1—C21101.8 (2)C15—C14—N3119.5 (3)
C1—S1—Ni196.99 (13)C19—C14—N3120.1 (3)
C21—S1—Ni1105.86 (16)C14—C15—C16120.1 (4)
C19—S2—C20103.5 (2)C14—C15—H15120.0
C2—C1—C6121.4 (4)C16—C15—H15120.0
C2—C1—S1120.8 (3)C17—C16—C15119.6 (4)
C6—C1—S1117.7 (3)C17—C16—H16120.2
C3—C2—C1120.0 (4)C15—C16—H16120.2
C3—C2—H2120.0C18—C17—C16120.9 (4)
C1—C2—H2120.0C18—C17—H17119.6
C4—C3—C2119.2 (4)C16—C17—H17119.6
C4—C3—H3120.4C17—C18—C19120.3 (4)
C2—C3—H3120.4C17—C18—H18119.8
C3—C4—C5122.1 (5)C19—C18—H18119.8
C3—C4—H4119.0C14—C19—C18118.6 (3)
C5—C4—H4119.0C14—C19—S2117.6 (3)
C4—C5—C6119.6 (4)C18—C19—S2123.8 (3)
C4—C5—H5120.2S2—C20—H20A109.5
C6—C5—H5120.2S2—C20—H20B109.5
C5—C6—N1126.9 (4)H20A—C20—H20B109.5
C5—C6—C1117.7 (4)S2—C20—H20C109.5
N1—C6—C1115.4 (3)H20A—C20—H20C109.5
O1—C7—N1128.8 (4)H20B—C20—H20C109.5
O1—C7—C8121.8 (3)S1—C21—H21A109.5
N1—C7—C8109.3 (3)S1—C21—H21B109.5
N2—C8—C9118.7 (4)H21A—C21—H21B109.5
N2—C8—C7112.6 (3)S1—C21—H21C109.5
C9—C8—C7128.7 (3)H21A—C21—H21C109.5
C10—C9—C8118.3 (4)H21B—C21—H21C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···O1i0.932.363.272 (6)168
C11—H11···O2ii0.932.773.134 (5)105
C18—H18···O2iii0.932.323.235 (5)167
Symmetry codes: (i) x, y+2, z; (ii) x+1, y+2, z; (iii) x+1, y1/2, z+1/2.
 

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