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In the title compound, [Ni(C18H35N2O2S2)2], the coordination geometry around the Ni atom, lying on a centre of symmetry, is square planar, consisting of four N atoms from the two vic-dioxime ligands. The O atoms are intra­molecularly hydrogen bonded, as is usually observed for anti-isomer metal complexes of vic-dioximes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046605/hy2030sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046605/hy2030Isup2.hkl
Contains datablock I

CCDC reference: 630012

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.059
  • wR factor = 0.066
  • Data-to-parameter ratio = 10.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.21 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.28 Ratio
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.122 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc. PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: DIAMOND (Brandenburg, 1996); software used to prepare material for publication: CRYSTALS.

Bis[N,N'-bis(octylsulfanyl)glyoximato]nickel(II) top
Crystal data top
[Ni(C18H35N2O2S2)2]F(000) = 1752
Mr = 809.95Dx = 1.232 Mg m3
Monoclinic, C2/cMelting point: 360 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 50.248 (5) ÅCell parameters from 11791 reflections
b = 5.322 (5) Åθ = 0.4–27.9°
c = 16.944 (5) ŵ = 0.68 mm1
β = 105.536 (5)°T = 293 K
V = 4366 (4) Å3Needle, red
Z = 40.43 × 0.06 × 0.05 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
5083 independent reflections
Radiation source: sealed tube2297 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.122
φ and ω scansθmax = 27.9°, θmin = 0.8°
Absorption correction: analytical
(de Meulenaer & Tompa, 1965)
h = 6564
Tmin = 0.77, Tmax = 0.97k = 66
14667 measured reflectionsl = 2213
Refinement top
Refinement on FPrimary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.066 w = (weight)[1-(ΔF/6σ(F))2]2,
where weight = 1.0/[0.737T0(x) + 0.674T1(x) + 0.412Tn-1(x)],
where Ti are the Chebychev polynomials and x = F /Fmax (Watkin, 1994; Prince, 1982)
S = 1.06(Δ/σ)max = 0.0004
2297 reflectionsΔρmax = 0.71 e Å3
223 parametersΔρmin = 0.60 e Å3
0 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.75000.25000.50000.0425
S20.66594 (3)0.5659 (3)0.41459 (9)0.0610
S10.71175 (3)0.8852 (3)0.34216 (7)0.0511
O20.69680 (7)0.1586 (7)0.5244 (2)0.0575
O10.76633 (7)0.6313 (6)0.40631 (19)0.0487
N10.74559 (8)0.5310 (8)0.4309 (2)0.0434
N20.71232 (7)0.3015 (8)0.4889 (2)0.0448
C20.70104 (10)0.4873 (10)0.4410 (3)0.0443
C50.67373 (11)0.5637 (11)0.1797 (3)0.0560
C10.72075 (10)0.6245 (9)0.4075 (3)0.0444
C30.72019 (10)0.7670 (11)0.2504 (3)0.0503
C60.65941 (12)0.3200 (12)0.1461 (3)0.0669
C120.61967 (11)0.3002 (12)0.3391 (4)0.0691
C40.70484 (10)0.5341 (10)0.2142 (3)0.0503
C110.64923 (11)0.2634 (12)0.3901 (4)0.0670
C130.60572 (11)0.0518 (13)0.3115 (4)0.0700
C140.57586 (12)0.0773 (14)0.2612 (4)0.0811
C70.62879 (12)0.3521 (12)0.1016 (4)0.0688
C80.61403 (13)0.1088 (13)0.0706 (4)0.0782
C90.58404 (14)0.1391 (15)0.0246 (5)0.0936
C150.56196 (13)0.1750 (15)0.2329 (5)0.0920
C180.48917 (17)0.373 (3)0.0981 (8)0.1870
C160.53226 (15)0.1499 (16)0.1797 (6)0.1079
C100.56999 (16)0.1103 (17)0.0036 (5)0.1118
C170.51882 (17)0.4003 (19)0.1509 (7)0.1401
H510.67050.68520.13520.0668*
H520.66600.62810.22250.0672*
H310.73980.73340.26410.0598*
H320.71590.89860.21060.0598*
H610.66880.24820.10780.0781*
H620.66080.20490.19120.0780*
H1210.61960.40040.29170.0804*
H1220.60940.38830.37220.0798*
H410.71250.47470.17130.0602*
H420.70800.40590.25660.0601*
H1110.65890.16530.35860.0795*
H1120.64940.17660.43980.0793*
H1310.61600.04000.27990.0812*
H1320.60560.04540.35960.0811*
H1410.57550.17790.21350.0930*
H1420.56560.16100.29380.0931*
H710.62760.46370.05560.0810*
H720.61970.42880.13900.0813*
H810.62330.02880.03400.0920*
H820.61510.00090.11690.0922*
H910.58290.24590.02260.1081*
H920.57440.21950.06030.1080*
H1510.57290.26450.20210.1039*
H1520.56160.27250.28130.1040*
H1810.48150.53670.08280.2560*
H1820.48910.27850.04990.2560*
H1830.47850.28640.12900.2560*
H1610.53230.04830.13240.1220*
H1620.52140.06540.21150.1220*
H1010.55070.08170.02810.1609*
H1020.57800.18610.04320.1610*
H1030.57210.22170.04250.1609*
H1710.52950.48600.11900.1550*
H1720.51860.50060.19880.1550*
H30.70870.05470.54790.0875*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0417 (4)0.0520 (6)0.0331 (4)0.0039 (5)0.0087 (3)0.0031 (4)
S20.0462 (7)0.0595 (9)0.0743 (9)0.0020 (7)0.0111 (6)0.0055 (7)
S10.0624 (8)0.0445 (8)0.0464 (7)0.0015 (6)0.0144 (6)0.0008 (6)
O20.0506 (18)0.072 (3)0.0519 (19)0.0012 (18)0.0168 (16)0.0195 (18)
O10.0510 (18)0.050 (2)0.0468 (17)0.0078 (17)0.0156 (15)0.0092 (16)
N10.050 (2)0.048 (2)0.0332 (18)0.005 (2)0.0135 (17)0.0008 (18)
N20.0428 (19)0.056 (3)0.0353 (18)0.000 (2)0.0104 (16)0.0026 (18)
C20.047 (2)0.047 (3)0.038 (2)0.002 (2)0.0094 (19)0.007 (2)
C50.059 (3)0.055 (3)0.052 (3)0.000 (3)0.013 (2)0.005 (3)
C10.049 (3)0.048 (3)0.034 (2)0.004 (2)0.0062 (19)0.005 (2)
C30.054 (3)0.059 (3)0.038 (2)0.006 (3)0.0122 (19)0.004 (3)
C60.067 (3)0.073 (4)0.055 (3)0.000 (3)0.007 (3)0.004 (3)
C120.051 (3)0.075 (5)0.073 (3)0.003 (3)0.004 (3)0.003 (3)
C40.060 (3)0.051 (3)0.040 (2)0.009 (3)0.014 (2)0.003 (2)
C110.056 (3)0.068 (4)0.073 (3)0.000 (3)0.012 (3)0.006 (3)
C130.055 (3)0.066 (4)0.081 (4)0.001 (3)0.006 (3)0.000 (3)
C140.055 (3)0.087 (5)0.090 (4)0.002 (4)0.001 (3)0.002 (4)
C70.071 (4)0.067 (4)0.065 (3)0.000 (3)0.013 (3)0.005 (3)
C80.076 (4)0.077 (5)0.077 (4)0.001 (4)0.012 (3)0.007 (4)
C90.069 (4)0.102 (6)0.100 (5)0.012 (4)0.006 (4)0.015 (5)
C150.062 (4)0.095 (6)0.103 (5)0.007 (4)0.007 (4)0.011 (4)
C180.080 (6)0.190 (13)0.242 (14)0.019 (7)0.042 (7)0.069 (11)
C160.069 (4)0.107 (6)0.128 (7)0.004 (5)0.008 (4)0.012 (5)
C100.085 (5)0.113 (7)0.124 (7)0.024 (5)0.006 (5)0.022 (6)
C170.093 (6)0.129 (9)0.167 (9)0.019 (6)0.020 (6)0.034 (7)
Geometric parameters (Å, º) top
Ni1—N1i1.876 (4)C11—H1120.958
Ni1—N2i1.872 (4)C13—C141.520 (7)
Ni1—N11.876 (4)C13—H1310.972
Ni1—N21.872 (4)C13—H1320.965
S2—C21.750 (5)C14—C151.530 (9)
S2—C111.812 (7)C14—H1410.967
S1—C11.757 (5)C14—H1420.959
S1—C31.829 (5)C7—C81.514 (9)
O2—N21.341 (5)C7—H710.968
O2—H30.832C7—H720.966
O1—N11.333 (5)C8—C91.508 (8)
N1—C11.303 (6)C8—H810.969
N2—C21.308 (6)C8—H820.968
C2—C11.463 (7)C9—C101.519 (10)
C5—C61.518 (8)C9—H910.970
C5—C41.523 (7)C9—H920.971
C5—H510.973C15—C161.529 (9)
C5—H520.971C15—H1510.977
C3—C41.502 (8)C15—H1520.975
C3—H310.966C18—C171.525 (10)
C3—H320.956C18—H1810.960
C6—C71.531 (8)C18—H1820.958
C6—H610.975C18—H1830.960
C6—H620.967C16—C171.515 (11)
C12—C111.518 (7)C16—H1610.968
C12—C131.510 (9)C16—H1620.972
C12—H1210.963C10—H1010.959
C12—H1220.977C10—H1020.959
C4—H410.963C10—H1030.964
C4—H420.972C17—H1710.972
C11—H1110.966C17—H1720.974
N1i—Ni1—N2i82.73 (17)C14—C13—H131109.1
N1i—Ni1—N1179.994C12—C13—H132108.4
N2i—Ni1—N197.27 (17)C14—C13—H132107.1
N1i—Ni1—N297.27 (17)H131—C13—H132108.6
N2i—Ni1—N2179.994C13—C14—C15113.4 (6)
N1—Ni1—N282.73 (17)C13—C14—H141108.2
C2—S2—C11102.7 (3)C15—C14—H141108.6
C1—S1—C3100.7 (2)C13—C14—H142108.6
N2—O2—H399.4C15—C14—H142108.5
O1—N1—Ni1122.9 (3)H141—C14—H142109.4
O1—N1—C1121.2 (4)C6—C7—C8114.2 (5)
Ni1—N1—C1116.0 (3)C6—C7—H71107.7
O2—N2—Ni1124.5 (3)C8—C7—H71109.0
O2—N2—C2119.9 (4)C6—C7—H72108.3
Ni1—N2—C2115.6 (3)C8—C7—H72108.3
S2—C2—N2125.4 (4)H71—C7—H72109.2
S2—C2—C1121.5 (4)C7—C8—C9114.6 (6)
N2—C2—C1113.1 (4)C7—C8—H81108.8
C6—C5—C4113.0 (5)C9—C8—H81107.6
C6—C5—H51108.3C7—C8—H82108.6
C4—C5—H51107.7C9—C8—H82108.3
C6—C5—H52109.7H81—C8—H82108.8
C4—C5—H52108.9C8—C9—C10112.6 (7)
H51—C5—H52109.1C8—C9—H91108.6
C2—C1—S1123.5 (4)C10—C9—H91109.5
C2—C1—N1112.6 (4)C8—C9—H92108.7
S1—C1—N1123.9 (4)C10—C9—H92108.3
S1—C3—C4114.9 (3)H91—C9—H92109.1
S1—C3—H31108.3C14—C15—C16113.6 (6)
C4—C3—H31108.9C14—C15—H151108.7
S1—C3—H32106.7C16—C15—H151109.1
C4—C3—H32108.7C14—C15—H152108.3
H31—C3—H32109.2C16—C15—H152107.8
C5—C6—C7113.7 (5)H151—C15—H152109.3
C5—C6—H61108.7C17—C18—H181109.3
C7—C6—H61108.3C17—C18—H182109.4
C5—C6—H62108.6H181—C18—H182109.6
C7—C6—H62108.0C17—C18—H183109.0
H61—C6—H62109.4H181—C18—H183109.9
C11—C12—C13111.4 (5)H182—C18—H183109.6
C11—C12—H121109.2C15—C16—C17113.2 (7)
C13—C12—H121109.3C15—C16—H161108.6
C11—C12—H122108.7C17—C16—H161108.9
C13—C12—H122109.0C15—C16—H162108.5
H121—C12—H122109.2C17—C16—H162108.5
C5—C4—C3115.7 (4)H161—C16—H162109.0
C5—C4—H41108.8C9—C10—H101109.2
C3—C4—H41108.2C9—C10—H102109.9
C5—C4—H42107.5H101—C10—H102109.3
C3—C4—H42108.3C9—C10—H103109.9
H41—C4—H42108.0H101—C10—H103109.2
C12—C11—S2109.8 (4)H102—C10—H103109.3
C12—C11—H111108.4C18—C17—C16112.7 (9)
S2—C11—H111109.6C18—C17—H171108.5
C12—C11—H112109.9C16—C17—H171109.1
S2—C11—H112109.4C18—C17—H172108.2
H111—C11—H112109.7C16—C17—H172108.5
C12—C13—C14113.7 (5)H171—C17—H172109.8
C12—C13—H131109.8
Symmetry code: (i) x+3/2, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H3···O1i0.831.622.455 (5)175
Symmetry code: (i) x+3/2, y+1/2, z+1.
 

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