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
CCDC reference: 627662
Key indicators
- Single-crystal X-ray study
- T = 289 K
- Mean (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
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 = 891.70 | Dx = 1.406 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 21 reflections |
a = 9.240 (3) Å | θ = 4.4–5.3° |
b = 16.124 (8) Å | µ = 0.78 mm−1 |
c = 14.148 (7) Å | T = 289 K |
β = 92.07 (4)° | Block, green |
V = 2106.4 (16) Å3 | 0.32 × 0.30 × 0.25 mm |
Z = 2 | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.024 |
Radiation source: fine-focus sealed tube | θmax = 25.5°, θmin = 1.9° |
Graphite monochromator | h = −11→11 |
ω–θ scans | k = 0→19 |
4138 measured reflections | l = −8→17 |
3911 independent reflections | 3 standard reflections every 300 reflections |
2616 reflections with I > 2σ(I) | intensity decay: 4% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-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 reflections | Δρmax = 0.67 e Å−3 |
253 parameters | Δρmin = −1.07 e Å−3 |
9 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
Ni | 0.0000 | 0.0000 | 0.0000 | 0.0372 (2) | |
P | −0.11608 (11) | 0.13743 (6) | 0.12003 (7) | 0.0463 (3) | |
S1 | 0.05184 (11) | 0.14670 (6) | 0.03798 (7) | 0.0470 (3) | |
S2 | −0.19570 (11) | 0.02321 (6) | 0.11541 (7) | 0.0490 (3) | |
O1 | −0.2344 (3) | 0.20619 (17) | 0.0967 (2) | 0.0581 (8) | |
O2 | −0.0828 (3) | 0.16856 (17) | 0.22454 (19) | 0.0577 (8) | |
N | −0.1467 (3) | 0.03614 (18) | −0.1112 (2) | 0.0424 (7) | |
C1 | −0.1146 (5) | 0.0958 (2) | −0.1726 (3) | 0.0499 (10) | |
C2 | −0.2113 (5) | 0.1261 (3) | −0.2397 (3) | 0.0631 (12) | |
C3 | −0.3485 (5) | 0.0945 (3) | −0.2445 (3) | 0.0684 (13) | |
C4 | −0.3839 (5) | 0.0322 (3) | −0.1834 (3) | 0.0627 (12) | |
C5 | −0.2810 (4) | 0.0051 (2) | −0.1184 (3) | 0.0501 (10) | |
C6 | −0.3110 (5) | 0.2036 (3) | 0.0062 (3) | 0.0584 (11) | |
C7 | −0.4105 (5) | 0.2769 (3) | −0.0030 (3) | 0.0667 (13) | |
C8 | −0.4971 (4) | 0.2711 (3) | −0.0952 (3) | 0.0554 (11) | |
C9 | −0.4533 (5) | 0.3134 (3) | −0.1732 (4) | 0.0636 (12) | |
C10 | −0.5305 (6) | 0.3062 (3) | −0.2581 (4) | 0.0755 (15) | |
C11 | −0.6499 (6) | 0.2560 (4) | −0.2645 (4) | 0.0850 (17) | |
C12 | −0.6920 (6) | 0.2141 (4) | −0.1881 (5) | 0.0976 (19) | |
C13 | −0.6154 (5) | 0.2219 (3) | −0.1036 (4) | 0.0775 (15) | |
C14 | 0.0186 (5) | 0.1219 (3) | 0.2835 (3) | 0.0581 (11) | |
C15 | 0.0048 (5) | 0.1523 (3) | 0.3825 (3) | 0.0628 (12) | |
C16 | 0.1005 (4) | 0.1086 (3) | 0.4542 (3) | 0.0541 (10) | |
C17 | 0.0672 (6) | 0.1135 (3) | 0.5476 (4) | 0.0752 (14) | |
C18 | 0.1518 (8) | 0.0744 (4) | 0.6163 (4) | 0.100 (2) | |
C19 | 0.2693 (9) | 0.0307 (4) | 0.5931 (5) | 0.106 (2) | |
C20 | 0.3026 (6) | 0.0235 (4) | 0.5012 (6) | 0.103 (2) | |
C21 | 0.2202 (6) | 0.0633 (4) | 0.4319 (4) | 0.0863 (17) | |
H1 | −0.0216 | 0.1180 | −0.1696 | 0.087 (4)* | |
H2 | −0.1840 | 0.1675 | −0.2813 | 0.087 (4)* | |
H3 | −0.4168 | 0.1148 | −0.2885 | 0.087 (4)* | |
H4 | −0.4760 | 0.0089 | −0.1860 | 0.087 (4)* | |
H5 | −0.3057 | −0.0372 | −0.0772 | 0.087 (4)* | |
H6A | −0.3665 | 0.1527 | 0.0006 | 0.086 (6)* | |
H6B | −0.2423 | 0.2046 | −0.0441 | 0.086 (6)* | |
H7A | −0.3545 | 0.3277 | −0.0014 | 0.086 (6)* | |
H7B | −0.4753 | 0.2777 | 0.0494 | 0.086 (6)* | |
H9 | −0.3715 | 0.3470 | −0.1689 | 0.087 (4)* | |
H10 | −0.5015 | 0.3353 | −0.3108 | 0.087 (4)* | |
H11 | −0.7018 | 0.2509 | −0.3217 | 0.087 (4)* | |
H12 | −0.7730 | 0.1799 | −0.1924 | 0.087 (4)* | |
H13 | −0.6455 | 0.1927 | −0.0511 | 0.087 (4)* | |
H14A | 0.1166 | 0.1304 | 0.2629 | 0.086 (6)* | |
H14B | −0.0034 | 0.0631 | 0.2797 | 0.086 (6)* | |
H15A | −0.0950 | 0.1459 | 0.4001 | 0.086 (6)* | |
H15B | 0.0274 | 0.2110 | 0.3844 | 0.086 (6)* | |
H17 | −0.0136 | 0.1436 | 0.5649 | 0.087 (4)* | |
H18 | 0.1274 | 0.0782 | 0.6794 | 0.087 (4)* | |
H19 | 0.3273 | 0.0057 | 0.6400 | 0.087 (4)* | |
H20 | 0.3815 | −0.0085 | 0.4846 | 0.087 (4)* | |
H21 | 0.2461 | 0.0593 | 0.3691 | 0.087 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni | 0.0402 (4) | 0.0321 (4) | 0.0395 (4) | −0.0009 (3) | 0.0046 (3) | 0.0009 (3) |
P | 0.0538 (6) | 0.0419 (6) | 0.0431 (6) | 0.0089 (5) | 0.0019 (5) | −0.0044 (4) |
S1 | 0.0537 (6) | 0.0350 (5) | 0.0525 (6) | −0.0034 (4) | 0.0026 (5) | 0.0006 (4) |
S2 | 0.0491 (6) | 0.0499 (6) | 0.0486 (6) | −0.0012 (4) | 0.0107 (5) | 0.0024 (5) |
O1 | 0.0676 (18) | 0.0581 (18) | 0.0481 (17) | 0.0240 (14) | −0.0048 (14) | −0.0077 (14) |
O2 | 0.0732 (18) | 0.0533 (17) | 0.0462 (17) | 0.0193 (15) | −0.0064 (14) | −0.0093 (13) |
N | 0.0425 (17) | 0.0383 (17) | 0.0467 (19) | 0.0002 (14) | 0.0051 (15) | −0.0029 (14) |
C1 | 0.061 (2) | 0.042 (2) | 0.048 (2) | 0.0017 (19) | 0.009 (2) | 0.0036 (18) |
C2 | 0.085 (3) | 0.054 (3) | 0.050 (3) | 0.009 (2) | 0.006 (2) | 0.014 (2) |
C3 | 0.075 (3) | 0.066 (3) | 0.063 (3) | 0.023 (3) | −0.012 (3) | 0.004 (2) |
C4 | 0.054 (2) | 0.061 (3) | 0.072 (3) | 0.003 (2) | −0.014 (2) | 0.001 (2) |
C5 | 0.050 (2) | 0.045 (2) | 0.055 (3) | 0.0008 (19) | 0.0003 (19) | 0.0018 (19) |
C6 | 0.064 (3) | 0.057 (3) | 0.055 (3) | 0.015 (2) | −0.005 (2) | −0.003 (2) |
C7 | 0.071 (3) | 0.061 (3) | 0.068 (3) | 0.022 (2) | −0.001 (2) | −0.001 (2) |
C8 | 0.051 (2) | 0.055 (3) | 0.060 (3) | 0.016 (2) | 0.006 (2) | 0.005 (2) |
C9 | 0.062 (3) | 0.053 (3) | 0.076 (3) | 0.007 (2) | 0.004 (3) | 0.003 (2) |
C10 | 0.087 (4) | 0.072 (3) | 0.068 (3) | 0.021 (3) | 0.010 (3) | 0.016 (3) |
C11 | 0.063 (3) | 0.110 (5) | 0.080 (4) | 0.022 (3) | −0.020 (3) | −0.005 (3) |
C12 | 0.053 (3) | 0.122 (5) | 0.117 (5) | −0.014 (3) | −0.005 (3) | 0.005 (4) |
C13 | 0.057 (3) | 0.089 (4) | 0.086 (4) | −0.003 (3) | 0.009 (3) | 0.026 (3) |
C14 | 0.067 (3) | 0.055 (3) | 0.052 (3) | 0.016 (2) | −0.003 (2) | −0.007 (2) |
C15 | 0.069 (3) | 0.069 (3) | 0.051 (3) | 0.017 (2) | 0.004 (2) | −0.013 (2) |
C16 | 0.059 (2) | 0.049 (2) | 0.055 (3) | −0.003 (2) | 0.002 (2) | −0.003 (2) |
C17 | 0.102 (4) | 0.065 (3) | 0.058 (3) | 0.008 (3) | 0.009 (3) | 0.002 (2) |
C18 | 0.161 (7) | 0.075 (4) | 0.063 (4) | 0.001 (4) | −0.006 (4) | 0.011 (3) |
C19 | 0.137 (6) | 0.082 (4) | 0.095 (5) | −0.006 (4) | −0.052 (5) | 0.023 (4) |
C20 | 0.063 (3) | 0.111 (5) | 0.134 (6) | 0.026 (3) | −0.022 (4) | 0.017 (5) |
C21 | 0.069 (3) | 0.109 (5) | 0.081 (4) | 0.020 (3) | 0.006 (3) | 0.002 (3) |
Geometric parameters (Å, º) top
Ni—S1 | 2.4686 (15) | C8—C9 | 1.370 (6) |
Ni—S2 | 2.5078 (14) | C9—C10 | 1.379 (7) |
Ni—N | 2.121 (3) | C9—H9 | 0.9300 |
P—S1 | 1.9766 (16) | C10—C11 | 1.368 (7) |
P—S2 | 1.9834 (17) | C10—H10 | 0.9300 |
P—O1 | 1.584 (3) | C11—C12 | 1.345 (8) |
P—O2 | 1.581 (3) | C11—H11 | 0.9300 |
O1—C6 | 1.440 (5) | C12—C13 | 1.373 (8) |
O2—C14 | 1.444 (5) | C12—H12 | 0.9300 |
N—C1 | 1.337 (5) | C13—H13 | 0.9300 |
N—C5 | 1.339 (5) | C14—C15 | 1.495 (6) |
C1—C2 | 1.370 (6) | C14—H14A | 0.9700 |
C1—H1 | 0.9300 | C14—H14B | 0.9700 |
C2—C3 | 1.366 (6) | C15—C16 | 1.497 (6) |
C2—H2 | 0.9300 | C15—H15A | 0.9700 |
C3—C4 | 1.372 (7) | C15—H15B | 0.9700 |
C3—H3 | 0.9300 | C16—C17 | 1.369 (6) |
C4—C5 | 1.370 (6) | C16—C21 | 1.373 (6) |
C4—H4 | 0.9300 | C17—C18 | 1.378 (8) |
C5—H5 | 0.9300 | C17—H17 | 0.9300 |
C6—C7 | 1.500 (6) | C18—C19 | 1.344 (9) |
C6—H6A | 0.9700 | C18—H18 | 0.9300 |
C6—H6B | 0.9700 | C19—C20 | 1.353 (9) |
C7—C8 | 1.508 (6) | C19—H19 | 0.9300 |
C7—H7A | 0.9700 | C20—C21 | 1.377 (8) |
C7—H7B | 0.9700 | C20—H20 | 0.9300 |
C8—C13 | 1.353 (6) | C21—H21 | 0.9300 |
| | | |
S1—Ni—S2 | 81.61 (3) | H7A—C7—H7B | 108.3 |
N—Ni—S1 | 90.69 (9) | C13—C8—C9 | 118.9 (5) |
N—Ni—S2 | 89.17 (8) | C13—C8—C7 | 120.9 (4) |
N—Ni—S1i | 89.31 (9) | C9—C8—C7 | 120.2 (4) |
N—Ni—S2i | 90.83 (8) | C8—C9—C10 | 120.0 (5) |
S1—Ni—S2i | 98.39 (3) | C8—C9—H9 | 120.0 |
Ni—Ni—S1 | 89.31 (9) | C10—C9—H9 | 120.0 |
Ni—Ni—S2 | 90.83 (8) | C11—C10—C9 | 119.9 (5) |
S1i—Ni—S1 | 180.0 | C11—C10—H10 | 120.0 |
N—Ni—Ni | 180.0 | C9—C10—H10 | 120.0 |
O2—P—O1 | 94.72 (15) | C12—C11—C10 | 120.0 (6) |
O2—P—S1 | 113.28 (13) | C12—C11—H11 | 120.0 |
O1—P—S1 | 112.04 (12) | C10—C11—H11 | 120.0 |
O2—P—S2 | 112.64 (13) | C11—C12—C13 | 119.9 (5) |
O1—P—S2 | 112.99 (13) | C11—C12—H12 | 120.0 |
S1—P—S2 | 110.42 (6) | C13—C12—H12 | 120.0 |
P—S1—Ni | 84.56 (4) | C8—C13—C12 | 121.3 (5) |
P—S2—Ni | 83.38 (4) | C8—C13—H13 | 119.4 |
C6—O1—P | 118.6 (2) | C12—C13—H13 | 119.4 |
C14—O2—P | 118.3 (2) | O2—C14—C15 | 107.1 (3) |
C1—N—C5 | 116.5 (4) | O2—C14—H14A | 110.3 |
C1—N—Ni | 121.9 (3) | C15—C14—H14A | 110.3 |
C5—N—Ni | 121.3 (3) | O2—C14—H14B | 110.3 |
N—C1—C2 | 123.5 (4) | C15—C14—H14B | 110.3 |
N—C1—H1 | 118.2 | H14A—C14—H14B | 108.5 |
C2—C1—H1 | 118.2 | C14—C15—C16 | 114.4 (3) |
C3—C2—C1 | 118.8 (4) | C14—C15—H15A | 108.7 |
C3—C2—H2 | 120.6 | C16—C15—H15A | 108.7 |
C1—C2—H2 | 120.6 | C14—C15—H15B | 108.7 |
C2—C3—C4 | 118.9 (4) | C16—C15—H15B | 108.7 |
C2—C3—H3 | 120.5 | H15A—C15—H15B | 107.6 |
C4—C3—H3 | 120.5 | C17—C16—C21 | 117.6 (5) |
C5—C4—C3 | 118.8 (4) | C17—C16—C15 | 118.6 (4) |
C5—C4—H4 | 120.6 | C21—C16—C15 | 123.8 (4) |
C3—C4—H4 | 120.6 | C16—C17—C18 | 120.9 (5) |
N—C5—C4 | 123.4 (4) | C16—C17—H17 | 119.6 |
N—C5—H5 | 118.3 | C18—C17—H17 | 119.6 |
C4—C5—H5 | 118.3 | C19—C18—C17 | 120.6 (6) |
O1—C6—C7 | 109.5 (3) | C19—C18—H18 | 119.7 |
O1—C6—H6A | 109.8 | C17—C18—H18 | 119.7 |
C7—C6—H6A | 109.8 | C18—C19—C20 | 119.6 (6) |
O1—C6—H6B | 109.8 | C18—C19—H19 | 120.2 |
C7—C6—H6B | 109.8 | C20—C19—H19 | 120.2 |
H6A—C6—H6B | 108.2 | C19—C20—C21 | 120.3 (6) |
C6—C7—C8 | 109.3 (4) | C19—C20—H20 | 119.8 |
C6—C7—H7A | 109.8 | C21—C20—H20 | 119.8 |
C8—C7—H7A | 109.8 | C16—C21—C20 | 120.9 (6) |
C6—C7—H7B | 109.8 | C16—C21—H21 | 119.5 |
C8—C7—H7B | 109.8 | C20—C21—H21 | 119.5 |
| | | |
O2—P—S1—Ni | 128.95 (12) | N—C1—C2—C3 | 0.4 (6) |
O1—P—S1—Ni | −125.34 (13) | C1—C2—C3—C4 | −1.4 (7) |
S2—P—S1—Ni | 1.55 (6) | C2—C3—C4—C5 | 1.2 (7) |
N—Ni—S1—P | 87.89 (9) | C1—N—C5—C4 | −1.0 (6) |
Ni—Ni—S1—P | −92.11 (9) | Ni—N—C5—C4 | 173.5 (3) |
S2i—Ni—S1—P | 178.84 (5) | C3—C4—C5—N | 0.0 (7) |
S2—Ni—S1—P | −1.16 (5) | P—O1—C6—C7 | −176.6 (3) |
O2—P—S2—Ni | −129.28 (12) | O1—C6—C7—C8 | −176.5 (4) |
O1—P—S2—Ni | 124.83 (12) | C6—C7—C8—C13 | 80.5 (5) |
S1—P—S2—Ni | −1.53 (6) | C6—C7—C8—C9 | −96.9 (5) |
N—Ni—S2—P | −89.66 (9) | C13—C8—C9—C10 | 0.8 (6) |
Ni—Ni—S2—P | 90.34 (9) | C7—C8—C9—C10 | 178.2 (4) |
S1i—Ni—S2—P | −178.84 (5) | C8—C9—C10—C11 | −0.7 (7) |
S1—Ni—S2—P | 1.16 (5) | C9—C10—C11—C12 | 0.3 (8) |
O2—P—O1—C6 | −176.3 (3) | C10—C11—C12—C13 | 0.1 (9) |
S1—P—O1—C6 | 66.2 (3) | C9—C8—C13—C12 | −0.4 (7) |
S2—P—O1—C6 | −59.3 (3) | C7—C8—C13—C12 | −177.8 (5) |
O1—P—O2—C14 | 176.6 (3) | C11—C12—C13—C8 | −0.1 (9) |
S1—P—O2—C14 | −67.0 (3) | P—O2—C14—C15 | −167.4 (3) |
S2—P—O2—C14 | 59.2 (3) | O2—C14—C15—C16 | 178.5 (3) |
S1i—Ni—N—C1 | −135.0 (3) | C14—C15—C16—C17 | −160.9 (4) |
S1—Ni—N—C1 | 45.0 (3) | C14—C15—C16—C21 | 18.8 (7) |
S2i—Ni—N—C1 | −53.4 (3) | C21—C16—C17—C18 | 0.3 (7) |
S2—Ni—N—C1 | 126.6 (3) | C15—C16—C17—C18 | 180.0 (5) |
S1i—Ni—N—C5 | 50.7 (3) | C16—C17—C18—C19 | 0.2 (8) |
S1—Ni—N—C5 | −129.3 (3) | C17—C18—C19—C20 | −1.6 (10) |
S2i—Ni—N—C5 | 132.3 (3) | C18—C19—C20—C21 | 2.6 (11) |
S2—Ni—N—C5 | −47.7 (3) | C17—C16—C21—C20 | 0.7 (8) |
C5—N—C1—C2 | 0.8 (5) | C15—C16—C21—C20 | −179.0 (5) |
Ni—N—C1—C2 | −173.7 (3) | C19—C20—C21—C16 | −2.1 (10) |
Symmetry code: (i) −x, −y, −z. |