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In the title complex, [Ni{S2P(OCH2CH2Ph)2}2(C5H5N)2], the octa­hedral NiII complex lies on an inversion centre. Important geometric data include: Ni—N = 2.121 (3) Å, Ni—S = 2.4686 (15) and 2.5078 (14) Å. The crystal packing is stabilized by π–π stacking inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806039936/gg2003sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806039936/gg2003Isup2.hkl
Contains datablock I

CCDC reference: 627662

Key indicators

  • Single-crystal X-ray study
  • T = 289 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.047
  • wR factor = 0.143
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.96
Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni - S2 .. 5.32 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C12 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT245_ALERT_2_C U(iso) H12 Smaller than U(eq) C12 by ... 0.01 AngSq PLAT245_ALERT_2_C U(iso) H18 Smaller than U(eq) C18 by ... 0.01 AngSq PLAT245_ALERT_2_C U(iso) H19 Smaller than U(eq) C19 by ... 0.02 AngSq PLAT245_ALERT_2_C U(iso) H20 Smaller than U(eq) C20 by ... 0.02 AngSq PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 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 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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: DIFRAC (Gabe et al., 1993); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 1998).

Bis[O,O'-bis(2-phenylethyl) dithiophosphato]dipyridinenickel(II) top
Crystal data top
[Ni(C16H18O4P2S4)2(C5H5N)2]F(000) = 932
Mr = 891.70Dx = 1.406 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 21 reflections
a = 9.240 (3) Åθ = 4.4–5.3°
b = 16.124 (8) ŵ = 0.78 mm1
c = 14.148 (7) ÅT = 289 K
β = 92.07 (4)°Block, green
V = 2106.4 (16) Å30.32 × 0.30 × 0.25 mm
Z = 2
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.024
Radiation source: fine-focus sealed tubeθmax = 25.5°, θmin = 1.9°
Graphite monochromatorh = 1111
ωθ scansk = 019
4138 measured reflectionsl = 817
3911 independent reflections3 standard reflections every 300 reflections
2616 reflections with I > 2σ(I) intensity decay: 4%
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)] = 0.047H-atom parameters constrained
wR(F2) = 0.143 w = 1/[σ2(Fo2) + (0.0787P)2 + 0.0752P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
3911 reflectionsΔρmax = 0.67 e Å3
253 parametersΔρmin = 1.07 e Å3
9 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.044 (3)
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
Ni0.00000.00000.00000.0372 (2)
P0.11608 (11)0.13743 (6)0.12003 (7)0.0463 (3)
S10.05184 (11)0.14670 (6)0.03798 (7)0.0470 (3)
S20.19570 (11)0.02321 (6)0.11541 (7)0.0490 (3)
O10.2344 (3)0.20619 (17)0.0967 (2)0.0581 (8)
O20.0828 (3)0.16856 (17)0.22454 (19)0.0577 (8)
N0.1467 (3)0.03614 (18)0.1112 (2)0.0424 (7)
C10.1146 (5)0.0958 (2)0.1726 (3)0.0499 (10)
C20.2113 (5)0.1261 (3)0.2397 (3)0.0631 (12)
C30.3485 (5)0.0945 (3)0.2445 (3)0.0684 (13)
C40.3839 (5)0.0322 (3)0.1834 (3)0.0627 (12)
C50.2810 (4)0.0051 (2)0.1184 (3)0.0501 (10)
C60.3110 (5)0.2036 (3)0.0062 (3)0.0584 (11)
C70.4105 (5)0.2769 (3)0.0030 (3)0.0667 (13)
C80.4971 (4)0.2711 (3)0.0952 (3)0.0554 (11)
C90.4533 (5)0.3134 (3)0.1732 (4)0.0636 (12)
C100.5305 (6)0.3062 (3)0.2581 (4)0.0755 (15)
C110.6499 (6)0.2560 (4)0.2645 (4)0.0850 (17)
C120.6920 (6)0.2141 (4)0.1881 (5)0.0976 (19)
C130.6154 (5)0.2219 (3)0.1036 (4)0.0775 (15)
C140.0186 (5)0.1219 (3)0.2835 (3)0.0581 (11)
C150.0048 (5)0.1523 (3)0.3825 (3)0.0628 (12)
C160.1005 (4)0.1086 (3)0.4542 (3)0.0541 (10)
C170.0672 (6)0.1135 (3)0.5476 (4)0.0752 (14)
C180.1518 (8)0.0744 (4)0.6163 (4)0.100 (2)
C190.2693 (9)0.0307 (4)0.5931 (5)0.106 (2)
C200.3026 (6)0.0235 (4)0.5012 (6)0.103 (2)
C210.2202 (6)0.0633 (4)0.4319 (4)0.0863 (17)
H10.02160.11800.16960.087 (4)*
H20.18400.16750.28130.087 (4)*
H30.41680.11480.28850.087 (4)*
H40.47600.00890.18600.087 (4)*
H50.30570.03720.07720.087 (4)*
H6A0.36650.15270.00060.086 (6)*
H6B0.24230.20460.04410.086 (6)*
H7A0.35450.32770.00140.086 (6)*
H7B0.47530.27770.04940.086 (6)*
H90.37150.34700.16890.087 (4)*
H100.50150.33530.31080.087 (4)*
H110.70180.25090.32170.087 (4)*
H120.77300.17990.19240.087 (4)*
H130.64550.19270.05110.087 (4)*
H14A0.11660.13040.26290.086 (6)*
H14B0.00340.06310.27970.086 (6)*
H15A0.09500.14590.40010.086 (6)*
H15B0.02740.21100.38440.086 (6)*
H170.01360.14360.56490.087 (4)*
H180.12740.07820.67940.087 (4)*
H190.32730.00570.64000.087 (4)*
H200.38150.00850.48460.087 (4)*
H210.24610.05930.36910.087 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni0.0402 (4)0.0321 (4)0.0395 (4)0.0009 (3)0.0046 (3)0.0009 (3)
P0.0538 (6)0.0419 (6)0.0431 (6)0.0089 (5)0.0019 (5)0.0044 (4)
S10.0537 (6)0.0350 (5)0.0525 (6)0.0034 (4)0.0026 (5)0.0006 (4)
S20.0491 (6)0.0499 (6)0.0486 (6)0.0012 (4)0.0107 (5)0.0024 (5)
O10.0676 (18)0.0581 (18)0.0481 (17)0.0240 (14)0.0048 (14)0.0077 (14)
O20.0732 (18)0.0533 (17)0.0462 (17)0.0193 (15)0.0064 (14)0.0093 (13)
N0.0425 (17)0.0383 (17)0.0467 (19)0.0002 (14)0.0051 (15)0.0029 (14)
C10.061 (2)0.042 (2)0.048 (2)0.0017 (19)0.009 (2)0.0036 (18)
C20.085 (3)0.054 (3)0.050 (3)0.009 (2)0.006 (2)0.014 (2)
C30.075 (3)0.066 (3)0.063 (3)0.023 (3)0.012 (3)0.004 (2)
C40.054 (2)0.061 (3)0.072 (3)0.003 (2)0.014 (2)0.001 (2)
C50.050 (2)0.045 (2)0.055 (3)0.0008 (19)0.0003 (19)0.0018 (19)
C60.064 (3)0.057 (3)0.055 (3)0.015 (2)0.005 (2)0.003 (2)
C70.071 (3)0.061 (3)0.068 (3)0.022 (2)0.001 (2)0.001 (2)
C80.051 (2)0.055 (3)0.060 (3)0.016 (2)0.006 (2)0.005 (2)
C90.062 (3)0.053 (3)0.076 (3)0.007 (2)0.004 (3)0.003 (2)
C100.087 (4)0.072 (3)0.068 (3)0.021 (3)0.010 (3)0.016 (3)
C110.063 (3)0.110 (5)0.080 (4)0.022 (3)0.020 (3)0.005 (3)
C120.053 (3)0.122 (5)0.117 (5)0.014 (3)0.005 (3)0.005 (4)
C130.057 (3)0.089 (4)0.086 (4)0.003 (3)0.009 (3)0.026 (3)
C140.067 (3)0.055 (3)0.052 (3)0.016 (2)0.003 (2)0.007 (2)
C150.069 (3)0.069 (3)0.051 (3)0.017 (2)0.004 (2)0.013 (2)
C160.059 (2)0.049 (2)0.055 (3)0.003 (2)0.002 (2)0.003 (2)
C170.102 (4)0.065 (3)0.058 (3)0.008 (3)0.009 (3)0.002 (2)
C180.161 (7)0.075 (4)0.063 (4)0.001 (4)0.006 (4)0.011 (3)
C190.137 (6)0.082 (4)0.095 (5)0.006 (4)0.052 (5)0.023 (4)
C200.063 (3)0.111 (5)0.134 (6)0.026 (3)0.022 (4)0.017 (5)
C210.069 (3)0.109 (5)0.081 (4)0.020 (3)0.006 (3)0.002 (3)
Geometric parameters (Å, º) top
Ni—S12.4686 (15)C8—C91.370 (6)
Ni—S22.5078 (14)C9—C101.379 (7)
Ni—N2.121 (3)C9—H90.9300
P—S11.9766 (16)C10—C111.368 (7)
P—S21.9834 (17)C10—H100.9300
P—O11.584 (3)C11—C121.345 (8)
P—O21.581 (3)C11—H110.9300
O1—C61.440 (5)C12—C131.373 (8)
O2—C141.444 (5)C12—H120.9300
N—C11.337 (5)C13—H130.9300
N—C51.339 (5)C14—C151.495 (6)
C1—C21.370 (6)C14—H14A0.9700
C1—H10.9300C14—H14B0.9700
C2—C31.366 (6)C15—C161.497 (6)
C2—H20.9300C15—H15A0.9700
C3—C41.372 (7)C15—H15B0.9700
C3—H30.9300C16—C171.369 (6)
C4—C51.370 (6)C16—C211.373 (6)
C4—H40.9300C17—C181.378 (8)
C5—H50.9300C17—H170.9300
C6—C71.500 (6)C18—C191.344 (9)
C6—H6A0.9700C18—H180.9300
C6—H6B0.9700C19—C201.353 (9)
C7—C81.508 (6)C19—H190.9300
C7—H7A0.9700C20—C211.377 (8)
C7—H7B0.9700C20—H200.9300
C8—C131.353 (6)C21—H210.9300
S1—Ni—S281.61 (3)H7A—C7—H7B108.3
N—Ni—S190.69 (9)C13—C8—C9118.9 (5)
N—Ni—S289.17 (8)C13—C8—C7120.9 (4)
N—Ni—S1i89.31 (9)C9—C8—C7120.2 (4)
N—Ni—S2i90.83 (8)C8—C9—C10120.0 (5)
S1—Ni—S2i98.39 (3)C8—C9—H9120.0
Ni—Ni—S189.31 (9)C10—C9—H9120.0
Ni—Ni—S290.83 (8)C11—C10—C9119.9 (5)
S1i—Ni—S1180.0C11—C10—H10120.0
N—Ni—Ni180.0C9—C10—H10120.0
O2—P—O194.72 (15)C12—C11—C10120.0 (6)
O2—P—S1113.28 (13)C12—C11—H11120.0
O1—P—S1112.04 (12)C10—C11—H11120.0
O2—P—S2112.64 (13)C11—C12—C13119.9 (5)
O1—P—S2112.99 (13)C11—C12—H12120.0
S1—P—S2110.42 (6)C13—C12—H12120.0
P—S1—Ni84.56 (4)C8—C13—C12121.3 (5)
P—S2—Ni83.38 (4)C8—C13—H13119.4
C6—O1—P118.6 (2)C12—C13—H13119.4
C14—O2—P118.3 (2)O2—C14—C15107.1 (3)
C1—N—C5116.5 (4)O2—C14—H14A110.3
C1—N—Ni121.9 (3)C15—C14—H14A110.3
C5—N—Ni121.3 (3)O2—C14—H14B110.3
N—C1—C2123.5 (4)C15—C14—H14B110.3
N—C1—H1118.2H14A—C14—H14B108.5
C2—C1—H1118.2C14—C15—C16114.4 (3)
C3—C2—C1118.8 (4)C14—C15—H15A108.7
C3—C2—H2120.6C16—C15—H15A108.7
C1—C2—H2120.6C14—C15—H15B108.7
C2—C3—C4118.9 (4)C16—C15—H15B108.7
C2—C3—H3120.5H15A—C15—H15B107.6
C4—C3—H3120.5C17—C16—C21117.6 (5)
C5—C4—C3118.8 (4)C17—C16—C15118.6 (4)
C5—C4—H4120.6C21—C16—C15123.8 (4)
C3—C4—H4120.6C16—C17—C18120.9 (5)
N—C5—C4123.4 (4)C16—C17—H17119.6
N—C5—H5118.3C18—C17—H17119.6
C4—C5—H5118.3C19—C18—C17120.6 (6)
O1—C6—C7109.5 (3)C19—C18—H18119.7
O1—C6—H6A109.8C17—C18—H18119.7
C7—C6—H6A109.8C18—C19—C20119.6 (6)
O1—C6—H6B109.8C18—C19—H19120.2
C7—C6—H6B109.8C20—C19—H19120.2
H6A—C6—H6B108.2C19—C20—C21120.3 (6)
C6—C7—C8109.3 (4)C19—C20—H20119.8
C6—C7—H7A109.8C21—C20—H20119.8
C8—C7—H7A109.8C16—C21—C20120.9 (6)
C6—C7—H7B109.8C16—C21—H21119.5
C8—C7—H7B109.8C20—C21—H21119.5
O2—P—S1—Ni128.95 (12)N—C1—C2—C30.4 (6)
O1—P—S1—Ni125.34 (13)C1—C2—C3—C41.4 (7)
S2—P—S1—Ni1.55 (6)C2—C3—C4—C51.2 (7)
N—Ni—S1—P87.89 (9)C1—N—C5—C41.0 (6)
Ni—Ni—S1—P92.11 (9)Ni—N—C5—C4173.5 (3)
S2i—Ni—S1—P178.84 (5)C3—C4—C5—N0.0 (7)
S2—Ni—S1—P1.16 (5)P—O1—C6—C7176.6 (3)
O2—P—S2—Ni129.28 (12)O1—C6—C7—C8176.5 (4)
O1—P—S2—Ni124.83 (12)C6—C7—C8—C1380.5 (5)
S1—P—S2—Ni1.53 (6)C6—C7—C8—C996.9 (5)
N—Ni—S2—P89.66 (9)C13—C8—C9—C100.8 (6)
Ni—Ni—S2—P90.34 (9)C7—C8—C9—C10178.2 (4)
S1i—Ni—S2—P178.84 (5)C8—C9—C10—C110.7 (7)
S1—Ni—S2—P1.16 (5)C9—C10—C11—C120.3 (8)
O2—P—O1—C6176.3 (3)C10—C11—C12—C130.1 (9)
S1—P—O1—C666.2 (3)C9—C8—C13—C120.4 (7)
S2—P—O1—C659.3 (3)C7—C8—C13—C12177.8 (5)
O1—P—O2—C14176.6 (3)C11—C12—C13—C80.1 (9)
S1—P—O2—C1467.0 (3)P—O2—C14—C15167.4 (3)
S2—P—O2—C1459.2 (3)O2—C14—C15—C16178.5 (3)
S1i—Ni—N—C1135.0 (3)C14—C15—C16—C17160.9 (4)
S1—Ni—N—C145.0 (3)C14—C15—C16—C2118.8 (7)
S2i—Ni—N—C153.4 (3)C21—C16—C17—C180.3 (7)
S2—Ni—N—C1126.6 (3)C15—C16—C17—C18180.0 (5)
S1i—Ni—N—C550.7 (3)C16—C17—C18—C190.2 (8)
S1—Ni—N—C5129.3 (3)C17—C18—C19—C201.6 (10)
S2i—Ni—N—C5132.3 (3)C18—C19—C20—C212.6 (11)
S2—Ni—N—C547.7 (3)C17—C16—C21—C200.7 (8)
C5—N—C1—C20.8 (5)C15—C16—C21—C20179.0 (5)
Ni—N—C1—C2173.7 (3)C19—C20—C21—C162.1 (10)
Symmetry code: (i) x, y, z.
 

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