Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051616/hb2592sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051616/hb2592Isup2.hkl |
CCDC reference: 667216
Key indicators
- Single-crystal X-ray study
- T = 98 K
- Mean (C-C) = 0.004 Å
- R factor = 0.042
- wR factor = 0.088
- Data-to-parameter ratio = 17.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.94 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.04
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.942 Tmax scaled 0.942 Tmin scaled 0.784 PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni (2) 1.88
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
For the synthesis, see Lai et al. (2004); Cox & Tiekink (1999). For related structures, see Tiekink & Haiduc (2005); Dakternieks et al. (2006).
The title compound was prepared by warming the parent nickel xanthate (Cox & Tiekink, 1999) with 1,2-bis(4-pyridyl)ethane in CHCl3 (20 ml) following a literature procedure (Lai et al., 2004). Green crystals of (I) were isolated by the slow evaporation of a of a 3:1 CHCl3/acetonitrile solution of the compound; m.p. 423–427 K.
The H atoms were included in the riding-model approximation with C—H distances = 0.95 to 1.00 Å, and with Uiso(methyl-H) = 1.5Ueq(methyl-C) and Uiso(H) = 1.2Ueq(remaining-C).
Nickel(II) xanthates, Ni(S2COR)2, are well known to form adducts with nitrogen-donors to generate aggregates of various topologies (Tiekink & Haiduc, 2005). In continuation of on-going studies in this area (Dakternieks et al., 2006), the title compound, (I), was prepared and characterized. The octahedrally coordinated Ni(II) centre in (I), Fig. 1, exists within a cis-N2S4 donor set (Table 1); the Ni atom lies on a crystallographic 2-fold axis and the bridging ligand is disposed about a centre of inversion. The xanthate ligand ligand coordinates in a symmetric mode with the Ni—S1 and Ni—S2 bond distances being 2.4110 (7) & 2.4509 (7) Å. The structure is polymeric and adopts a zigzag topology as is often observed in such adducts (Tiekink & Haiduc, 2005), as shown in Fig. 2.
For the synthesis, see Lai et al. (2004); Cox & Tiekink (1999). For related structures, see Tiekink & Haiduc (2005); Dakternieks et al. (2006).
Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
[Ni(C4H7OS2)2(C12H12N2)] | F(000) = 1072 |
Mr = 513.38 | Dx = 1.452 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -C 2yc | Cell parameters from 1905 reflections |
a = 10.1460 (6) Å | θ = 2.9–30.0° |
b = 15.8638 (10) Å | µ = 1.20 mm−1 |
c = 15.0545 (9) Å | T = 98 K |
β = 104.256 (3)° | Fragment, green |
V = 2348.5 (2) Å3 | 0.30 × 0.11 × 0.05 mm |
Z = 4 |
Rigaku AFC12κ/SATURN724 diffractometer | 2348 independent reflections |
Radiation source: fine-focus sealed tube | 2243 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ω scans | θmax = 26.5°, θmin = 2.4° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = 0→12 |
Tmin = 0.832, Tmax = 1 | k = −19→19 |
3974 measured reflections | l = −18→18 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 1.19 | w = 1/[σ2(Fo2) + (0.0265P)2 + 7.5757P] where P = (Fo2 + 2Fc2)/3 |
2348 reflections | (Δ/σ)max < 0.001 |
132 parameters | Δρmax = 0.57 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
[Ni(C4H7OS2)2(C12H12N2)] | V = 2348.5 (2) Å3 |
Mr = 513.38 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 10.1460 (6) Å | µ = 1.20 mm−1 |
b = 15.8638 (10) Å | T = 98 K |
c = 15.0545 (9) Å | 0.30 × 0.11 × 0.05 mm |
β = 104.256 (3)° |
Rigaku AFC12κ/SATURN724 diffractometer | 2348 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2243 reflections with I > 2σ(I) |
Tmin = 0.832, Tmax = 1 | Rint = 0.019 |
3974 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 1.19 | Δρmax = 0.57 e Å−3 |
2348 reflections | Δρmin = −0.28 e Å−3 |
132 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Ni | 0.0000 | 0.25754 (3) | 0.2500 | 0.01712 (13) | |
S1 | 0.11332 (7) | 0.24132 (4) | 0.12782 (4) | 0.02205 (16) | |
S2 | 0.17407 (7) | 0.14873 (4) | 0.29958 (4) | 0.02095 (16) | |
O2 | 0.31745 (19) | 0.13301 (12) | 0.18192 (13) | 0.0241 (4) | |
N1 | 0.1411 (2) | 0.34583 (13) | 0.31920 (14) | 0.0193 (4) | |
C1 | 0.2118 (3) | 0.17161 (17) | 0.19961 (17) | 0.0202 (5) | |
C2 | 0.3651 (3) | 0.1563 (2) | 0.10060 (19) | 0.0287 (6) | |
H2 | 0.2861 | 0.1678 | 0.0474 | 0.034* | |
C3 | 0.4532 (3) | 0.2335 (2) | 0.1236 (2) | 0.0348 (7) | |
H3A | 0.3977 | 0.2813 | 0.1341 | 0.052* | |
H3B | 0.4940 | 0.2466 | 0.0726 | 0.052* | |
H3C | 0.5253 | 0.2229 | 0.1791 | 0.052* | |
C4 | 0.4439 (4) | 0.0799 (2) | 0.0814 (2) | 0.0434 (8) | |
H4A | 0.3822 | 0.0317 | 0.0657 | 0.065* | |
H4B | 0.5160 | 0.0665 | 0.1360 | 0.065* | |
H4C | 0.4845 | 0.0923 | 0.0301 | 0.065* | |
C5 | 0.1958 (3) | 0.33574 (17) | 0.40860 (17) | 0.0204 (5) | |
H5 | 0.1530 | 0.2978 | 0.4415 | 0.024* | |
C6 | 0.3101 (3) | 0.37706 (18) | 0.45547 (18) | 0.0234 (6) | |
H6 | 0.3445 | 0.3676 | 0.5193 | 0.028* | |
C7 | 0.3758 (3) | 0.43277 (17) | 0.40978 (19) | 0.0241 (6) | |
C8 | 0.3171 (3) | 0.44529 (17) | 0.31804 (19) | 0.0254 (6) | |
H8 | 0.3566 | 0.4839 | 0.2838 | 0.031* | |
C9 | 0.2010 (3) | 0.40162 (17) | 0.27593 (18) | 0.0231 (6) | |
H9 | 0.1617 | 0.4119 | 0.2128 | 0.028* | |
C10 | 0.5056 (3) | 0.4752 (2) | 0.4583 (2) | 0.0326 (7) | |
H10A | 0.5343 | 0.5138 | 0.4148 | 0.039* | |
H10B | 0.5772 | 0.4319 | 0.4771 | 0.039* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni | 0.0166 (2) | 0.0197 (3) | 0.0142 (2) | 0.000 | 0.00224 (17) | 0.000 |
S1 | 0.0205 (3) | 0.0290 (4) | 0.0163 (3) | 0.0013 (3) | 0.0039 (2) | 0.0028 (2) |
S2 | 0.0229 (3) | 0.0230 (3) | 0.0178 (3) | 0.0029 (3) | 0.0066 (2) | 0.0023 (2) |
O2 | 0.0211 (10) | 0.0291 (10) | 0.0243 (10) | 0.0007 (8) | 0.0098 (8) | 0.0000 (8) |
N1 | 0.0199 (11) | 0.0168 (11) | 0.0196 (11) | 0.0009 (9) | 0.0019 (9) | −0.0001 (8) |
C1 | 0.0179 (12) | 0.0236 (13) | 0.0188 (12) | −0.0007 (10) | 0.0040 (10) | −0.0018 (10) |
C2 | 0.0261 (14) | 0.0390 (18) | 0.0243 (14) | −0.0011 (13) | 0.0126 (12) | −0.0005 (12) |
C3 | 0.0298 (16) | 0.0459 (19) | 0.0285 (15) | −0.0035 (14) | 0.0068 (13) | 0.0048 (14) |
C4 | 0.0361 (19) | 0.055 (2) | 0.046 (2) | −0.0044 (16) | 0.0232 (16) | −0.0098 (17) |
C5 | 0.0224 (13) | 0.0205 (13) | 0.0178 (12) | −0.0023 (11) | 0.0040 (10) | 0.0003 (10) |
C6 | 0.0229 (14) | 0.0271 (14) | 0.0182 (13) | −0.0018 (11) | 0.0016 (11) | −0.0009 (10) |
C7 | 0.0233 (14) | 0.0231 (14) | 0.0263 (14) | −0.0037 (11) | 0.0068 (11) | −0.0060 (11) |
C8 | 0.0328 (15) | 0.0208 (14) | 0.0244 (14) | −0.0054 (12) | 0.0103 (12) | 0.0016 (11) |
C9 | 0.0254 (14) | 0.0219 (13) | 0.0201 (13) | 0.0000 (11) | 0.0019 (11) | 0.0024 (10) |
C10 | 0.0261 (15) | 0.0399 (18) | 0.0326 (16) | −0.0139 (13) | 0.0085 (12) | −0.0114 (14) |
Ni—N1 | 2.089 (2) | C3—H3C | 0.9800 |
Ni—N1i | 2.089 (2) | C4—H4A | 0.9800 |
Ni—S1 | 2.4110 (7) | C4—H4B | 0.9800 |
Ni—S1i | 2.4110 (7) | C4—H4C | 0.9800 |
Ni—S2i | 2.4509 (7) | C5—C6 | 1.367 (4) |
Ni—S2 | 2.4509 (7) | C5—H5 | 0.9500 |
S1—C1 | 1.690 (3) | C6—C7 | 1.387 (4) |
S2—C1 | 1.681 (3) | C6—H6 | 0.9500 |
O2—C1 | 1.318 (3) | C7—C8 | 1.377 (4) |
O2—C2 | 1.470 (3) | C7—C10 | 1.499 (4) |
N1—C9 | 1.331 (3) | C8—C9 | 1.379 (4) |
N1—C5 | 1.333 (3) | C8—H8 | 0.9500 |
C2—C3 | 1.505 (4) | C9—H9 | 0.9500 |
C2—C4 | 1.518 (4) | C10—C10ii | 1.510 (6) |
C2—H2 | 1.0000 | C10—H10A | 0.9900 |
C3—H3A | 0.9800 | C10—H10B | 0.9900 |
C3—H3B | 0.9800 | ||
N1—Ni—N1i | 95.78 (12) | H3A—C3—H3B | 109.5 |
N1—Ni—S1 | 93.15 (6) | C2—C3—H3C | 109.5 |
N1i—Ni—S1 | 95.06 (6) | H3A—C3—H3C | 109.5 |
N1—Ni—S1i | 95.06 (6) | H3B—C3—H3C | 109.5 |
N1i—Ni—S1i | 93.15 (6) | C2—C4—H4A | 109.5 |
S1—Ni—S1i | 167.74 (4) | C2—C4—H4B | 109.5 |
N1—Ni—S2i | 168.04 (6) | H4A—C4—H4B | 109.5 |
N1i—Ni—S2i | 88.07 (6) | C2—C4—H4C | 109.5 |
S1—Ni—S2i | 97.80 (2) | H4A—C4—H4C | 109.5 |
S1i—Ni—S2i | 73.38 (2) | H4B—C4—H4C | 109.5 |
N1—Ni—S2 | 88.07 (6) | N1—C5—C6 | 123.6 (2) |
N1i—Ni—S2 | 168.04 (6) | N1—C5—H5 | 118.2 |
S1—Ni—S2 | 73.38 (2) | C6—C5—H5 | 118.2 |
S1i—Ni—S2 | 97.80 (2) | C5—C6—C7 | 120.0 (2) |
S2i—Ni—S2 | 90.45 (4) | C5—C6—H6 | 120.0 |
C1—S1—Ni | 84.25 (9) | C7—C6—H6 | 120.0 |
C1—S2—Ni | 83.17 (9) | C8—C7—C6 | 116.6 (2) |
C1—O2—C2 | 120.1 (2) | C8—C7—C10 | 122.3 (3) |
C9—N1—C5 | 116.6 (2) | C6—C7—C10 | 121.1 (3) |
C9—N1—Ni | 122.77 (18) | C7—C8—C9 | 119.9 (3) |
C5—N1—Ni | 119.13 (18) | C7—C8—H8 | 120.1 |
O2—C1—S2 | 117.2 (2) | C9—C8—H8 | 120.1 |
O2—C1—S1 | 123.9 (2) | N1—C9—C8 | 123.4 (2) |
S2—C1—S1 | 118.98 (16) | N1—C9—H9 | 118.3 |
O2—C2—C3 | 108.2 (2) | C8—C9—H9 | 118.3 |
O2—C2—C4 | 104.7 (2) | C7—C10—C10ii | 113.7 (3) |
C3—C2—C4 | 112.5 (3) | C7—C10—H10A | 108.8 |
O2—C2—H2 | 110.4 | C10ii—C10—H10A | 108.8 |
C3—C2—H2 | 110.4 | C7—C10—H10B | 108.8 |
C4—C2—H2 | 110.4 | C10ii—C10—H10B | 108.8 |
C2—C3—H3A | 109.5 | H10A—C10—H10B | 107.7 |
C2—C3—H3B | 109.5 | ||
N1—Ni—S1—C1 | 84.26 (11) | C2—O2—C1—S2 | −173.59 (19) |
N1i—Ni—S1—C1 | −179.65 (11) | C2—O2—C1—S1 | 6.8 (3) |
S1i—Ni—S1—C1 | −47.77 (9) | Ni—S2—C1—O2 | 176.0 (2) |
S2i—Ni—S1—C1 | −90.91 (9) | Ni—S2—C1—S1 | −4.38 (15) |
S2—Ni—S1—C1 | −2.78 (9) | Ni—S1—C1—O2 | −176.0 (2) |
N1—Ni—S2—C1 | −91.07 (11) | Ni—S1—C1—S2 | 4.44 (15) |
N1i—Ni—S2—C1 | 18.0 (3) | C1—O2—C2—C3 | 82.0 (3) |
S1—Ni—S2—C1 | 2.80 (9) | C1—O2—C2—C4 | −157.9 (2) |
S1i—Ni—S2—C1 | 174.09 (9) | C9—N1—C5—C6 | −2.3 (4) |
S2i—Ni—S2—C1 | 100.81 (9) | Ni—N1—C5—C6 | 164.1 (2) |
N1i—Ni—N1—C9 | −61.03 (19) | N1—C5—C6—C7 | −0.2 (4) |
S1—Ni—N1—C9 | 34.4 (2) | C5—C6—C7—C8 | 2.2 (4) |
S1i—Ni—N1—C9 | −154.7 (2) | C5—C6—C7—C10 | −176.5 (3) |
S2i—Ni—N1—C9 | −169.4 (2) | C6—C7—C8—C9 | −1.7 (4) |
S2—Ni—N1—C9 | 107.6 (2) | C10—C7—C8—C9 | 177.0 (3) |
N1i—Ni—N1—C5 | 133.5 (2) | C5—N1—C9—C8 | 2.8 (4) |
S1—Ni—N1—C5 | −131.04 (19) | Ni—N1—C9—C8 | −163.0 (2) |
S1i—Ni—N1—C5 | 39.9 (2) | C7—C8—C9—N1 | −0.9 (4) |
S2i—Ni—N1—C5 | 25.2 (4) | C8—C7—C10—C10ii | 124.9 (4) |
S2—Ni—N1—C5 | −57.81 (19) | C6—C7—C10—C10ii | −56.5 (5) |
Symmetry codes: (i) −x, y, −z+1/2; (ii) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C4H7OS2)2(C12H12N2)] |
Mr | 513.38 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 98 |
a, b, c (Å) | 10.1460 (6), 15.8638 (10), 15.0545 (9) |
β (°) | 104.256 (3) |
V (Å3) | 2348.5 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.20 |
Crystal size (mm) | 0.30 × 0.11 × 0.05 |
Data collection | |
Diffractometer | Rigaku AFC12κ/SATURN724 |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.832, 1 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3974, 2348, 2243 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.088, 1.19 |
No. of reflections | 2348 |
No. of parameters | 132 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.57, −0.28 |
Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006).
Ni—N1 | 2.089 (2) | Ni—S2 | 2.4509 (7) |
Ni—S1 | 2.4110 (7) | ||
S1—Ni—S2 | 73.38 (2) |
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Nickel(II) xanthates, Ni(S2COR)2, are well known to form adducts with nitrogen-donors to generate aggregates of various topologies (Tiekink & Haiduc, 2005). In continuation of on-going studies in this area (Dakternieks et al., 2006), the title compound, (I), was prepared and characterized. The octahedrally coordinated Ni(II) centre in (I), Fig. 1, exists within a cis-N2S4 donor set (Table 1); the Ni atom lies on a crystallographic 2-fold axis and the bridging ligand is disposed about a centre of inversion. The xanthate ligand ligand coordinates in a symmetric mode with the Ni—S1 and Ni—S2 bond distances being 2.4110 (7) & 2.4509 (7) Å. The structure is polymeric and adopts a zigzag topology as is often observed in such adducts (Tiekink & Haiduc, 2005), as shown in Fig. 2.