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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): m129.
Published online 2010 January 9. doi:  10.1107/S1600536809055639
PMCID: PMC2979951

Bis(pyridine-κN){N 2,N 2′-[1,1′-(pyridine-2,6-di­yl)diethyl­idyne]benzene­sulfono­hydrazonato-κ5 O,N,N′,N′′,O′}nickel(II)

Abstract

In the crystal structure of the title compound, [Ni(C21H19N5O4S2)(C5H5N)2], the metal center is seven-coordinate, with an approximate penta­gonal-bipyramidal configuration. The Ni atom is chelated by a dianionic penta­dentate Schiff base via the pyridine N atom, the two azomethine N atoms and the two sulfonyl O atoms. The latter coordinate to Ni at different distances, viz. 2.3337 (12) and 2.7988 (12) Å. Two apically coordinated pyridine mol­ecules complete the seven-coordin­ate geometry. The dihedral angle between the two pyridine ring planes is 68.25 (6)°.

Related literature

For the structure of the ligand and its zinc(II) complex, see: Yusnita et al. (2009a [triangle]). For the structure of copper(II) complex of a similar ligand, see: Yusnita et al. (2009b [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m129-scheme1.jpg

Experimental

Crystal data

  • [Ni(C21H19N5O4S2)(C5H5N)2]
  • M r = 686.44
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m129-efi1.jpg
  • a = 11.6029 (2) Å
  • b = 15.8298 (3) Å
  • c = 16.4156 (3) Å
  • β = 91.823 (2)°
  • V = 3013.55 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.83 mm−1
  • T = 100 K
  • 0.30 × 0.22 × 0.19 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.788, T max = 0.858
  • 22997 measured reflections
  • 5308 independent reflections
  • 4815 reflections with I > 2σ(I)
  • R int = 0.020

Refinement

  • R[F 2 > 2σ(F 2)] = 0.024
  • wR(F 2) = 0.065
  • S = 1.05
  • 5308 reflections
  • 406 parameters
  • H-atom parameters constrained
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809055639/om2309sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055639/om2309Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the University of Malaya for funding this study (UMRG grant No. RG136/09HTM).

supplementary crystallographic information

Experimental

2,6-Diacetylpyridinebis(benzenesulfonylhydrazide) (1.413 g, 3 mmol) was dissolved in ethanol (50 ml) and three droplets of triethylamine were added, followed by addition of an ethanolic solution of stoichiometric amount of hydrated nickel (II) acetate. The mixture was refluxed for 5 h. The resulting dark brown solids were filtered and dried over silica gel. Brown crystals of the title compound were grown by slow evaporation of a pyridine solution.

Refinement

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.98 Å), and were treated as riding on their parent atoms, with U(H) set to 1.2–1.5 times Ueq(C).

Figures

Fig. 1.
Thermal ellipsoid plot of the title compound at the 40% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

[Ni(C21H19N5O4S2)(C5H5N)2]F(000) = 1428
Mr = 686.44Dx = 1.515 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9879 reflections
a = 11.6029 (2) Åθ = 2.5–28.3°
b = 15.8298 (3) ŵ = 0.83 mm1
c = 16.4156 (3) ÅT = 100 K
β = 91.823 (2)°Block, brown
V = 3013.55 (9) Å30.30 × 0.22 × 0.19 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer5308 independent reflections
Radiation source: fine-focus sealed tube4815 reflections with I > 2σ(I)
graphiteRint = 0.020
[var phi] and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→13
Tmin = 0.788, Tmax = 0.858k = −18→18
22997 measured reflectionsl = −19→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0291P)2 + 2.4638P] where P = (Fo2 + 2Fc2)/3
5308 reflections(Δ/σ)max = 0.001
406 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = −0.36 e Å3

Special details

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)

xyzUiso*/Ueq
Ni0.410517 (18)0.141485 (13)0.215880 (12)0.01157 (7)
S10.59292 (4)−0.00687 (3)0.18463 (3)0.01400 (10)
S20.27045 (4)0.12194 (3)0.40344 (2)0.01272 (10)
O10.60699 (11)−0.09339 (8)0.16025 (8)0.0207 (3)
O20.49868 (10)0.01082 (7)0.23919 (7)0.0157 (3)
O30.33543 (10)0.06141 (7)0.35665 (7)0.0166 (3)
O40.17478 (10)0.08872 (8)0.44772 (7)0.0174 (3)
N10.38858 (12)0.24587 (9)0.14898 (8)0.0127 (3)
N20.28461 (12)0.21687 (9)0.28339 (8)0.0125 (3)
N30.22201 (12)0.19994 (9)0.35170 (8)0.0137 (3)
N40.52548 (12)0.12310 (9)0.12007 (9)0.0134 (3)
N50.58722 (12)0.05107 (9)0.10487 (9)0.0156 (3)
N60.53749 (12)0.19065 (9)0.29575 (9)0.0143 (3)
N70.27701 (12)0.07348 (9)0.15452 (9)0.0140 (3)
C10.25986 (14)0.28945 (11)0.24972 (10)0.0131 (3)
C20.17637 (15)0.35009 (11)0.28509 (11)0.0169 (4)
H2A0.10360.32090.29480.025*
H2B0.16230.39680.24690.025*
H2C0.20840.37230.33670.025*
C30.32043 (14)0.30847 (11)0.17453 (10)0.0131 (3)
C40.31328 (15)0.38448 (11)0.13167 (11)0.0166 (4)
H40.26530.42900.14940.020*
C50.37776 (15)0.39357 (11)0.06257 (11)0.0182 (4)
H50.37420.44500.03280.022*
C60.44751 (15)0.32834 (11)0.03648 (10)0.0163 (4)
H60.49130.3342−0.01110.020*
C70.45153 (14)0.25424 (11)0.08200 (10)0.0139 (3)
C80.52355 (14)0.18075 (11)0.06381 (10)0.0145 (4)
C90.58566 (16)0.17241 (12)−0.01367 (11)0.0209 (4)
H9A0.58510.2268−0.04210.031*
H9B0.54730.1297−0.04830.031*
H9C0.66550.1551−0.00170.031*
C100.72211 (15)0.02117 (11)0.24006 (11)0.0169 (4)
C110.78134 (15)0.09477 (12)0.22277 (11)0.0208 (4)
H110.75560.13040.17930.025*
C120.87894 (17)0.11586 (14)0.26986 (12)0.0275 (5)
H120.91970.16650.25900.033*
C130.91686 (16)0.06321 (15)0.33268 (12)0.0305 (5)
H130.98410.07750.36420.037*
C140.85730 (17)−0.00988 (14)0.34959 (12)0.0288 (5)
H140.8834−0.04550.39300.035*
C150.75943 (16)−0.03152 (13)0.30345 (11)0.0227 (4)
H150.7183−0.08180.31500.027*
C160.36809 (14)0.16219 (11)0.48003 (10)0.0140 (3)
C170.41986 (15)0.10464 (12)0.53378 (11)0.0192 (4)
H170.40480.04590.52800.023*
C180.49334 (17)0.13345 (13)0.59570 (11)0.0233 (4)
H180.52880.09450.63280.028*
C190.51522 (16)0.21932 (13)0.60359 (11)0.0236 (4)
H190.56560.23920.64610.028*
C200.46384 (17)0.27609 (12)0.54965 (12)0.0235 (4)
H200.47920.33480.55530.028*
C210.39001 (15)0.24778 (11)0.48730 (11)0.0188 (4)
H210.35500.28670.45010.023*
C220.57825 (16)0.26962 (12)0.28800 (12)0.0211 (4)
H220.54900.30330.24420.025*
C230.66049 (17)0.30403 (13)0.34058 (13)0.0277 (5)
H230.68670.36030.33310.033*
C240.70418 (17)0.25566 (13)0.40424 (12)0.0267 (4)
H240.76160.27760.44090.032*
C250.66268 (15)0.17464 (12)0.41350 (11)0.0205 (4)
H250.69060.14000.45710.025*
C260.57989 (15)0.14469 (11)0.35850 (10)0.0161 (4)
H260.55160.08890.36540.019*
C270.28759 (15)0.04331 (11)0.07836 (11)0.0170 (4)
H270.35660.05480.05080.020*
C280.20283 (16)−0.00357 (11)0.03843 (11)0.0197 (4)
H280.2130−0.0225−0.01580.024*
C290.10303 (16)−0.02267 (12)0.07827 (11)0.0203 (4)
H290.0444−0.05610.05260.024*
C300.09044 (16)0.00798 (12)0.15641 (12)0.0205 (4)
H300.0227−0.00390.18540.025*
C310.17797 (15)0.05617 (11)0.19157 (11)0.0178 (4)
H310.16770.07820.24470.021*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni0.01215 (12)0.01122 (12)0.01132 (12)0.00032 (8)0.00009 (8)0.00054 (8)
S10.0129 (2)0.0136 (2)0.0155 (2)0.00219 (16)0.00011 (16)−0.00047 (16)
S20.0127 (2)0.0124 (2)0.0131 (2)−0.00030 (16)0.00112 (16)−0.00026 (16)
O10.0209 (7)0.0145 (6)0.0266 (7)0.0039 (5)−0.0017 (5)−0.0031 (5)
O20.0139 (6)0.0156 (6)0.0177 (6)0.0009 (5)0.0019 (5)0.0016 (5)
O30.0159 (6)0.0149 (6)0.0191 (6)0.0006 (5)0.0013 (5)−0.0028 (5)
O40.0165 (6)0.0180 (6)0.0180 (6)−0.0024 (5)0.0031 (5)0.0015 (5)
N10.0128 (7)0.0137 (7)0.0113 (7)0.0001 (6)−0.0011 (6)−0.0001 (6)
N20.0125 (7)0.0146 (7)0.0104 (7)−0.0016 (6)−0.0004 (5)−0.0016 (6)
N30.0140 (7)0.0162 (7)0.0110 (7)0.0011 (6)0.0018 (6)−0.0008 (6)
N40.0117 (7)0.0145 (7)0.0140 (7)0.0014 (6)0.0000 (6)−0.0017 (6)
N50.0153 (7)0.0167 (8)0.0149 (7)0.0040 (6)0.0022 (6)−0.0016 (6)
N60.0126 (7)0.0154 (7)0.0150 (7)0.0002 (6)0.0025 (6)−0.0004 (6)
N70.0150 (7)0.0122 (7)0.0147 (7)0.0027 (6)−0.0009 (6)−0.0003 (6)
C10.0129 (8)0.0146 (8)0.0116 (8)0.0003 (7)−0.0024 (6)−0.0024 (7)
C20.0184 (9)0.0177 (9)0.0146 (9)0.0042 (7)0.0006 (7)−0.0011 (7)
C30.0117 (8)0.0134 (8)0.0140 (8)−0.0004 (7)−0.0029 (7)−0.0022 (7)
C40.0180 (9)0.0134 (9)0.0181 (9)0.0013 (7)−0.0025 (7)0.0001 (7)
C50.0211 (9)0.0150 (9)0.0183 (9)−0.0024 (7)−0.0037 (7)0.0042 (7)
C60.0171 (9)0.0177 (9)0.0138 (9)−0.0024 (7)−0.0005 (7)0.0029 (7)
C70.0121 (8)0.0169 (9)0.0126 (8)−0.0023 (7)−0.0018 (7)−0.0004 (7)
C80.0133 (8)0.0167 (9)0.0136 (9)−0.0022 (7)0.0002 (7)0.0007 (7)
C90.0228 (10)0.0223 (10)0.0179 (9)0.0012 (8)0.0058 (8)0.0013 (8)
C100.0131 (8)0.0220 (9)0.0156 (9)0.0043 (7)0.0018 (7)−0.0046 (7)
C110.0159 (9)0.0259 (10)0.0207 (10)0.0005 (8)0.0034 (7)−0.0033 (8)
C120.0169 (9)0.0357 (12)0.0301 (11)−0.0047 (8)0.0054 (8)−0.0115 (9)
C130.0138 (9)0.0548 (14)0.0226 (10)0.0055 (9)−0.0012 (8)−0.0169 (10)
C140.0240 (10)0.0454 (13)0.0168 (10)0.0133 (10)−0.0029 (8)−0.0057 (9)
C150.0223 (10)0.0274 (10)0.0184 (10)0.0060 (8)0.0023 (8)−0.0016 (8)
C160.0124 (8)0.0177 (9)0.0120 (8)0.0006 (7)0.0021 (6)−0.0001 (7)
C170.0200 (9)0.0176 (9)0.0201 (10)−0.0009 (7)0.0014 (7)0.0039 (7)
C180.0224 (10)0.0284 (11)0.0188 (10)0.0011 (8)−0.0038 (8)0.0077 (8)
C190.0223 (10)0.0307 (11)0.0173 (9)−0.0025 (8)−0.0058 (8)−0.0014 (8)
C200.0268 (10)0.0180 (9)0.0254 (10)−0.0020 (8)−0.0055 (8)−0.0034 (8)
C210.0202 (9)0.0170 (9)0.0191 (9)0.0018 (7)−0.0028 (7)0.0012 (7)
C220.0206 (9)0.0197 (10)0.0228 (10)−0.0045 (8)−0.0012 (8)0.0045 (8)
C230.0260 (10)0.0245 (10)0.0324 (11)−0.0115 (8)−0.0042 (9)0.0029 (9)
C240.0200 (10)0.0345 (12)0.0251 (11)−0.0067 (9)−0.0054 (8)−0.0033 (9)
C250.0161 (9)0.0290 (10)0.0164 (9)0.0024 (8)−0.0012 (7)0.0020 (8)
C260.0144 (9)0.0183 (9)0.0158 (9)0.0021 (7)0.0038 (7)0.0000 (7)
C270.0188 (9)0.0163 (9)0.0160 (9)0.0020 (7)0.0019 (7)−0.0006 (7)
C280.0234 (10)0.0200 (9)0.0156 (9)0.0048 (8)−0.0018 (7)−0.0053 (7)
C290.0180 (9)0.0174 (9)0.0249 (10)0.0018 (7)−0.0062 (8)−0.0059 (8)
C300.0152 (9)0.0235 (10)0.0227 (10)0.0003 (8)0.0012 (7)−0.0034 (8)
C310.0184 (9)0.0189 (9)0.0163 (9)0.0018 (7)0.0015 (7)−0.0036 (7)

Geometric parameters (Å, °)

Ni—N11.9959 (14)C9—H9C0.9800
Ni—N62.0910 (14)C10—C111.387 (3)
Ni—N42.1145 (14)C10—C151.392 (3)
Ni—N72.1152 (14)C11—C121.391 (3)
Ni—N22.2111 (14)C11—H110.9500
Ni—O22.3337 (12)C12—C131.387 (3)
Ni—O32.7988 (12)C12—H120.9500
S1—O11.4376 (13)C13—C141.380 (3)
S1—O21.4624 (12)C13—H130.9500
S1—N51.5984 (15)C14—C151.388 (3)
S1—C101.7847 (18)C14—H140.9500
S2—O41.4450 (12)C15—H150.9500
S2—O31.4538 (12)C16—C211.383 (3)
S2—N31.5911 (15)C16—C171.391 (2)
S2—C161.7832 (17)C17—C181.383 (3)
N1—C31.343 (2)C17—H170.9500
N1—C71.346 (2)C18—C191.388 (3)
N2—C11.303 (2)C18—H180.9500
N2—N31.3816 (19)C19—C201.383 (3)
N4—C81.298 (2)C19—H190.9500
N4—N51.374 (2)C20—C211.388 (3)
N6—C261.342 (2)C20—H200.9500
N6—C221.344 (2)C21—H210.9500
N7—C311.345 (2)C22—C231.378 (3)
N7—C271.348 (2)C22—H220.9500
C1—C31.471 (2)C23—C241.379 (3)
C1—C21.494 (2)C23—H230.9500
C2—H2A0.9800C24—C251.380 (3)
C2—H2B0.9800C24—H240.9500
C2—H2C0.9800C25—C261.381 (3)
C3—C41.395 (2)C25—H250.9500
C4—C51.386 (3)C26—H260.9500
C4—H40.9500C27—C281.381 (3)
C5—C61.388 (3)C27—H270.9500
C5—H50.9500C28—C291.381 (3)
C6—C71.391 (2)C28—H280.9500
C6—H60.9500C29—C301.384 (3)
C7—C81.469 (2)C29—H290.9500
C8—C91.488 (2)C30—C311.382 (3)
C9—H9A0.9800C30—H300.9500
C9—H9B0.9800C31—H310.9500
N1—Ni—N696.42 (6)N4—C8—C7114.16 (15)
N1—Ni—N477.12 (6)N4—C8—C9123.23 (16)
N6—Ni—N493.96 (5)C7—C8—C9122.58 (15)
N1—Ni—N794.63 (6)C8—C9—H9A109.5
N6—Ni—N7168.17 (6)C8—C9—H9B109.5
N4—Ni—N792.61 (5)H9A—C9—H9B109.5
N1—Ni—N275.77 (5)C8—C9—H9C109.5
N6—Ni—N287.04 (5)H9A—C9—H9C109.5
N4—Ni—N2152.81 (5)H9B—C9—H9C109.5
N7—Ni—N291.59 (5)C11—C10—C15120.81 (17)
N1—Ni—O2150.64 (5)C11—C10—S1121.21 (14)
N6—Ni—O286.02 (5)C15—C10—S1117.93 (14)
N4—Ni—O273.52 (5)C10—C11—C12119.19 (18)
N7—Ni—O286.42 (5)C10—C11—H11120.4
N2—Ni—O2133.58 (5)C12—C11—H11120.4
N1—Ni—O3142.34 (5)C13—C12—C11120.2 (2)
N6—Ni—O383.25 (5)C13—C12—H12119.9
N4—Ni—O3140.54 (5)C11—C12—H12119.9
N7—Ni—O385.42 (5)C14—C13—C12120.28 (18)
N2—Ni—O366.59 (4)C14—C13—H13119.9
O2—Ni—O367.02 (4)C12—C13—H13119.9
O1—S1—O2116.53 (7)C13—C14—C15120.23 (19)
O1—S1—N5108.70 (8)C13—C14—H14119.9
O2—S1—N5112.31 (7)C15—C14—H14119.9
O1—S1—C10106.14 (8)C14—C15—C10119.33 (19)
O2—S1—C10105.81 (8)C14—C15—H15120.3
N5—S1—C10106.69 (8)C10—C15—H15120.3
O4—S2—O3116.46 (7)C21—C16—C17120.82 (16)
O4—S2—N3106.68 (7)C21—C16—S2121.46 (13)
O3—S2—N3114.18 (7)C17—C16—S2117.71 (14)
O4—S2—C16104.86 (7)C18—C17—C16119.59 (17)
O3—S2—C16106.23 (7)C18—C17—H17120.2
N3—S2—C16107.75 (8)C16—C17—H17120.2
S1—O2—Ni113.69 (7)C17—C18—C19119.87 (17)
S2—O3—Ni108.55 (6)C17—C18—H18120.1
C3—N1—C7121.51 (15)C19—C18—H18120.1
C3—N1—Ni120.33 (11)C20—C19—C18120.18 (18)
C7—N1—Ni117.91 (11)C20—C19—H19119.9
C1—N2—N3113.63 (14)C18—C19—H19119.9
C1—N2—Ni113.80 (11)C19—C20—C21120.38 (18)
N3—N2—Ni132.44 (11)C19—C20—H20119.8
N2—N3—S2113.45 (11)C21—C20—H20119.8
C8—N4—N5116.85 (14)C16—C21—C20119.16 (17)
C8—N4—Ni115.81 (11)C16—C21—H21120.4
N5—N4—Ni126.47 (11)C20—C21—H21120.4
N4—N5—S1109.62 (11)N6—C22—C23123.16 (17)
C26—N6—C22117.09 (15)N6—C22—H22118.4
C26—N6—Ni120.89 (12)C23—C22—H22118.4
C22—N6—Ni122.00 (12)C22—C23—C24119.05 (18)
C31—N7—C27116.84 (15)C22—C23—H23120.5
C31—N7—Ni120.77 (12)C24—C23—H23120.5
C27—N7—Ni122.36 (12)C23—C24—C25118.58 (18)
N2—C1—C3115.57 (15)C23—C24—H24120.7
N2—C1—C2122.58 (15)C25—C24—H24120.7
C3—C1—C2121.85 (15)C24—C25—C26118.99 (17)
C1—C2—H2A109.5C24—C25—H25120.5
C1—C2—H2B109.5C26—C25—H25120.5
H2A—C2—H2B109.5N6—C26—C25123.11 (17)
C1—C2—H2C109.5N6—C26—H26118.4
H2A—C2—H2C109.5C25—C26—H26118.4
H2B—C2—H2C109.5N7—C27—C28123.12 (17)
N1—C3—C4120.33 (15)N7—C27—H27118.4
N1—C3—C1114.38 (15)C28—C27—H27118.4
C4—C3—C1125.27 (15)C27—C28—C29119.21 (17)
C5—C4—C3118.51 (16)C27—C28—H28120.4
C5—C4—H4120.7C29—C28—H28120.4
C3—C4—H4120.7C28—C29—C30118.49 (17)
C4—C5—C6120.69 (16)C28—C29—H29120.8
C4—C5—H5119.7C30—C29—H29120.8
C6—C5—H5119.7C31—C30—C29118.88 (17)
C5—C6—C7118.14 (16)C31—C30—H30120.6
C5—C6—H6120.9C29—C30—H30120.6
C7—C6—H6120.9N7—C31—C30123.42 (16)
N1—C7—C6120.81 (16)N7—C31—H31118.3
N1—C7—C8114.53 (15)C30—C31—H31118.3
C6—C7—C8124.65 (15)
O1—S1—O2—Ni−145.14 (7)O3—Ni—N7—C3133.11 (13)
N5—S1—O2—Ni−18.82 (10)N1—Ni—N7—C2772.98 (14)
C10—S1—O2—Ni97.20 (8)N6—Ni—N7—C27−128.0 (3)
N1—Ni—O2—S18.70 (14)N4—Ni—N7—C27−4.30 (14)
N6—Ni—O2—S1−87.33 (8)N2—Ni—N7—C27148.83 (13)
N4—Ni—O2—S17.99 (7)O2—Ni—N7—C27−77.61 (13)
N7—Ni—O2—S1101.78 (8)O3—Ni—N7—C27−144.81 (13)
N2—Ni—O2—S1−169.43 (6)N3—N2—C1—C3−177.23 (13)
O3—Ni—O2—S1−171.68 (8)Ni—N2—C1—C3−0.80 (18)
O4—S2—O3—Ni145.87 (6)N3—N2—C1—C23.3 (2)
N3—S2—O3—Ni20.78 (9)Ni—N2—C1—C2179.72 (12)
C16—S2—O3—Ni−97.82 (7)C7—N1—C3—C40.0 (2)
N1—Ni—O3—S2−12.32 (11)Ni—N1—C3—C4174.16 (12)
N6—Ni—O3—S279.45 (7)C7—N1—C3—C1−178.66 (15)
N4—Ni—O3—S2167.49 (7)Ni—N1—C3—C1−4.52 (19)
N7—Ni—O3—S2−103.97 (7)N2—C1—C3—N13.3 (2)
N2—Ni—O3—S2−10.24 (6)C2—C1—C3—N1−177.22 (15)
O2—Ni—O3—S2167.98 (8)N2—C1—C3—C4−175.31 (16)
N6—Ni—N1—C3−82.17 (13)C2—C1—C3—C44.2 (3)
N4—Ni—N1—C3−174.78 (13)N1—C3—C4—C50.0 (3)
N7—Ni—N1—C393.59 (13)C1—C3—C4—C5178.56 (16)
N2—Ni—N1—C33.12 (12)C3—C4—C5—C60.3 (3)
O2—Ni—N1—C3−175.48 (10)C4—C5—C6—C7−0.6 (3)
O3—Ni—N1—C35.10 (17)C3—N1—C7—C6−0.4 (2)
N6—Ni—N1—C792.18 (12)Ni—N1—C7—C6−174.65 (12)
N4—Ni—N1—C7−0.43 (12)C3—N1—C7—C8178.48 (14)
N7—Ni—N1—C7−92.05 (12)Ni—N1—C7—C84.20 (19)
N2—Ni—N1—C7177.47 (13)C5—C6—C7—N10.6 (3)
O2—Ni—N1—C7−1.13 (19)C5—C6—C7—C8−178.08 (16)
O3—Ni—N1—C7179.45 (10)N5—N4—C8—C7177.13 (14)
N1—Ni—N2—C1−1.11 (11)Ni—N4—C8—C77.13 (19)
N6—Ni—N2—C196.28 (12)N5—N4—C8—C9−1.0 (2)
N4—Ni—N2—C13.37 (19)Ni—N4—C8—C9−171.04 (13)
N7—Ni—N2—C1−95.48 (12)N1—C7—C8—N4−7.5 (2)
O2—Ni—N2—C1177.94 (10)C6—C7—C8—N4171.34 (16)
O3—Ni—N2—C1−179.80 (13)N1—C7—C8—C9170.72 (16)
N1—Ni—N2—N3174.46 (15)C6—C7—C8—C9−10.5 (3)
N6—Ni—N2—N3−88.15 (14)O1—S1—C10—C11130.91 (15)
N4—Ni—N2—N3178.94 (12)O2—S1—C10—C11−104.67 (15)
N7—Ni—N2—N380.09 (14)N5—S1—C10—C1115.11 (17)
O2—Ni—N2—N3−6.49 (17)O1—S1—C10—C15−51.50 (16)
O3—Ni—N2—N3−4.23 (13)O2—S1—C10—C1572.92 (15)
C1—N2—N3—S2−167.49 (12)N5—S1—C10—C15−167.30 (14)
Ni—N2—N3—S216.94 (18)C15—C10—C11—C12−0.2 (3)
O4—S2—N3—N2−155.04 (11)S1—C10—C11—C12177.28 (14)
O3—S2—N3—N2−24.92 (14)C10—C11—C12—C130.7 (3)
C16—S2—N3—N292.82 (12)C11—C12—C13—C14−0.8 (3)
N1—Ni—N4—C8−3.93 (12)C12—C13—C14—C150.5 (3)
N6—Ni—N4—C8−99.62 (13)C13—C14—C15—C100.0 (3)
N7—Ni—N4—C890.22 (13)C11—C10—C15—C14−0.1 (3)
N2—Ni—N4—C8−8.4 (2)S1—C10—C15—C14−177.72 (14)
O2—Ni—N4—C8175.71 (13)O4—S2—C16—C21−112.94 (15)
O3—Ni—N4—C8176.19 (10)O3—S2—C16—C21123.19 (15)
N1—Ni—N4—N5−172.83 (14)N3—S2—C16—C210.43 (17)
N6—Ni—N4—N591.48 (13)O4—S2—C16—C1765.61 (15)
N7—Ni—N4—N5−78.68 (13)O3—S2—C16—C17−58.26 (15)
N2—Ni—N4—N5−177.28 (11)N3—S2—C16—C17178.98 (13)
O2—Ni—N4—N56.81 (12)C21—C16—C17—C180.6 (3)
O3—Ni—N4—N57.29 (17)S2—C16—C17—C18−177.96 (14)
C8—N4—N5—S1172.91 (12)C16—C17—C18—C19−0.2 (3)
Ni—N4—N5—S1−18.29 (16)C17—C18—C19—C20−0.1 (3)
O1—S1—N5—N4153.45 (11)C18—C19—C20—C210.1 (3)
O2—S1—N5—N423.01 (13)C17—C16—C21—C20−0.6 (3)
C10—S1—N5—N4−92.48 (12)S2—C16—C21—C20177.89 (14)
N1—Ni—N6—C26176.50 (13)C19—C20—C21—C160.3 (3)
N4—Ni—N6—C26−106.03 (13)C26—N6—C22—C230.4 (3)
N7—Ni—N6—C2617.5 (3)Ni—N6—C22—C23178.89 (15)
N2—Ni—N6—C26101.19 (13)N6—C22—C23—C240.3 (3)
O2—Ni—N6—C26−32.88 (13)C22—C23—C24—C25−0.8 (3)
O3—Ni—N6—C2634.42 (12)C23—C24—C25—C260.5 (3)
N1—Ni—N6—C22−1.92 (14)C22—N6—C26—C25−0.7 (2)
N4—Ni—N6—C2275.54 (14)Ni—N6—C26—C25−179.16 (13)
N7—Ni—N6—C22−160.9 (2)C24—C25—C26—N60.2 (3)
N2—Ni—N6—C22−77.23 (14)C31—N7—C27—C28−0.2 (3)
O2—Ni—N6—C22148.70 (14)Ni—N7—C27—C28177.80 (13)
O3—Ni—N6—C22−144.00 (14)N7—C27—C28—C29−1.6 (3)
N1—Ni—N7—C31−109.10 (13)C27—C28—C29—C301.7 (3)
N6—Ni—N7—C3149.9 (3)C28—C29—C30—C31−0.2 (3)
N4—Ni—N7—C31173.62 (13)C27—N7—C31—C301.8 (3)
N2—Ni—N7—C31−33.25 (13)Ni—N7—C31—C30−176.19 (14)
O2—Ni—N7—C31100.31 (13)C29—C30—C31—N7−1.7 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2309).

References

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