Acta Cryst. (2012). E68, m1544 [ doi:10.1107/S1600536812047691 ]
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2N,N')bis(thiocyanato-N)tin(IV)The SnIV atom in the title compound, [Sn(CH3)2(NCS)2(C12H8N2)], is located on a twofold rotation axis in a distorted octahedral enviroment. The methyl groups are trans to each other [C-Sn-C = 175.7 (3)°], whereas the thiocyanate groups are cis to each other.
Dimethyltin dithiocyanate (0.27 g, 1 mmol) and 1,10-phenanthroline hydrate (0.19 g, 1 mmol) were loaded into a convection tube; the tube was filled with ethyl alcohol and kept at 333 K. Colorless crystals were collected from the side arm after several days.
Carbon-bound H-atoms were placed in calculated positions [C–H 0.93 to 0.96 Å, Uiso(H) 1.2 to 1.5Ueq(C)] and were included in the refinement in the riding model approximation.
Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).
![[Figure 1]](./bt6862fig1thm.gif)
| Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of (CH3)2Sn(NCS)2(C12H8N2) at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. |
| [Sn(CH3)2(NCS)2(C12H8N2)] | F(000) = 880 |
| Mr = 445.12 | Dx = 1.616 Mg m−3 |
| Orthorhombic, Pccn | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ab 2ac | Cell parameters from 1757 reflections |
| a = 6.8218 (7) Å | θ = 3.2–27.5° |
| b = 12.9272 (13) Å | µ = 1.63 mm−1 |
| c = 20.746 (2) Å | T = 295 K |
| V = 1829.5 (3) Å3 | Prism, colorless |
| Z = 4 | 0.30 × 0.15 × 0.05 mm |
| Agilent SuperNova Dual diffractometer with an Atlas detector | 2116 independent reflections |
| Radiation source: SuperNova (Mo) X-ray Source | 1368 reflections with I > 2σ(I) |
| Mirror monochromator | Rint = 0.055 |
| Detector resolution: 10.4041 pixels mm-1 | θmax = 27.6°, θmin = 3.2° |
| ω scan | h = −6→8 |
| Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −16→16 |
| Tmin = 0.641, Tmax = 0.923 | l = −27→24 |
| 10262 measured reflections |
| 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)] = 0.039 | H-atom parameters constrained |
| wR(F2) = 0.106 | w = 1/[σ2(Fo2) + (0.0429P)2 + 0.5974P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.01 | (Δ/σ)max = 0.001 |
| 2116 reflections | Δρmax = 0.51 e Å−3 |
| 106 parameters | Δρmin = −0.63 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0024 (4) |
| [Sn(CH3)2(NCS)2(C12H8N2)] | V = 1829.5 (3) Å3 |
| Mr = 445.12 | Z = 4 |
| Orthorhombic, Pccn | Mo Kα radiation |
| a = 6.8218 (7) Å | µ = 1.63 mm−1 |
| b = 12.9272 (13) Å | T = 295 K |
| c = 20.746 (2) Å | 0.30 × 0.15 × 0.05 mm |
| Agilent SuperNova Dual diffractometer with an Atlas detector | 2116 independent reflections |
| Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | 1368 reflections with I > 2σ(I) |
| Tmin = 0.641, Tmax = 0.923 | Rint = 0.055 |
| 10262 measured reflections | θmax = 27.6° |
| R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
| wR(F2) = 0.106 | Δρmax = 0.51 e Å−3 |
| S = 1.01 | Δρmin = −0.63 e Å−3 |
| 2116 reflections | Absolute structure: ? |
| 106 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
| x | y | z | Uiso*/Ueq | ||
| Sn1 | 0.7500 | 0.2500 | 0.243352 (18) | 0.04816 (19) | |
| S1 | 0.3311 (2) | 0.45584 (12) | 0.09896 (7) | 0.0957 (6) | |
| N1 | 0.5798 (5) | 0.3037 (3) | 0.33508 (16) | 0.0515 (8) | |
| N2 | 0.5246 (7) | 0.3231 (4) | 0.1785 (2) | 0.1073 (18) | |
| C1 | 0.5903 (7) | 0.1114 (4) | 0.2395 (2) | 0.0746 (14) | |
| H1A | 0.6337 | 0.0710 | 0.2034 | 0.112* | |
| H1B | 0.4533 | 0.1267 | 0.2349 | 0.112* | |
| H1C | 0.6109 | 0.0731 | 0.2786 | 0.112* | |
| C2 | 0.4146 (7) | 0.3576 (4) | 0.3337 (3) | 0.0736 (14) | |
| H2 | 0.3600 | 0.3748 | 0.2941 | 0.088* | |
| C3 | 0.3208 (10) | 0.3891 (5) | 0.3898 (4) | 0.107 (2) | |
| H3 | 0.2060 | 0.4276 | 0.3875 | 0.128* | |
| C4 | 0.3969 (12) | 0.3635 (6) | 0.4470 (4) | 0.115 (3) | |
| H4 | 0.3327 | 0.3832 | 0.4846 | 0.138* | |
| C5 | 0.5721 (10) | 0.3073 (5) | 0.4510 (3) | 0.0882 (18) | |
| C6 | 0.6600 (6) | 0.2783 (3) | 0.3924 (2) | 0.0556 (11) | |
| C7 | 0.6688 (15) | 0.2767 (9) | 0.5097 (3) | 0.142 (5) | |
| H7 | 0.6135 | 0.2956 | 0.5490 | 0.170* | |
| C8 | 0.4443 (7) | 0.3778 (4) | 0.1449 (2) | 0.0644 (12) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Sn1 | 0.0574 (3) | 0.0459 (3) | 0.0411 (3) | 0.00503 (18) | 0.000 | 0.000 |
| S1 | 0.1188 (12) | 0.0817 (11) | 0.0866 (11) | 0.0168 (9) | −0.0541 (9) | −0.0028 (8) |
| N1 | 0.056 (2) | 0.043 (2) | 0.055 (2) | 0.0032 (17) | 0.0090 (16) | −0.0054 (17) |
| N2 | 0.127 (4) | 0.085 (4) | 0.110 (4) | 0.010 (3) | −0.058 (3) | 0.019 (3) |
| C1 | 0.081 (4) | 0.065 (3) | 0.078 (4) | −0.010 (3) | −0.014 (2) | −0.009 (3) |
| C2 | 0.062 (3) | 0.054 (3) | 0.105 (4) | 0.005 (2) | 0.023 (3) | −0.010 (3) |
| C3 | 0.085 (4) | 0.075 (4) | 0.161 (7) | −0.002 (3) | 0.061 (5) | −0.028 (5) |
| C4 | 0.137 (6) | 0.096 (5) | 0.113 (6) | −0.044 (5) | 0.087 (5) | −0.050 (5) |
| C5 | 0.123 (5) | 0.082 (4) | 0.059 (3) | −0.039 (4) | 0.038 (3) | −0.022 (3) |
| C6 | 0.071 (3) | 0.052 (3) | 0.044 (2) | −0.021 (2) | 0.014 (2) | −0.008 (2) |
| C7 | 0.225 (15) | 0.156 (12) | 0.044 (3) | −0.092 (10) | 0.035 (4) | −0.019 (4) |
| C8 | 0.071 (3) | 0.068 (3) | 0.054 (3) | −0.001 (3) | −0.015 (2) | −0.009 (2) |
| Sn1—C1 | 2.098 (5) | C1—H1C | 0.9600 |
| Sn1—C1i | 2.098 (5) | C2—C3 | 1.388 (8) |
| Sn1—N2i | 2.251 (4) | C2—H2 | 0.9300 |
| Sn1—N2 | 2.251 (4) | C3—C4 | 1.337 (10) |
| Sn1—N1 | 2.335 (3) | C3—H3 | 0.9300 |
| Sn1—N1i | 2.335 (3) | C4—C5 | 1.401 (9) |
| S1—C8 | 1.588 (5) | C4—H4 | 0.9300 |
| N1—C2 | 1.326 (5) | C5—C6 | 1.405 (6) |
| N1—C6 | 1.350 (5) | C5—C7 | 1.442 (9) |
| N2—C8 | 1.134 (5) | C6—C6i | 1.430 (9) |
| C1—H1A | 0.9600 | C7—C7i | 1.31 (2) |
| C1—H1B | 0.9600 | C7—H7 | 0.9300 |
| C1—Sn1—C1i | 175.7 (3) | Sn1—C1—H1C | 109.5 |
| C1—Sn1—N2i | 88.48 (19) | H1A—C1—H1C | 109.5 |
| C1i—Sn1—N2i | 88.94 (18) | H1B—C1—H1C | 109.5 |
| C1—Sn1—N2 | 88.94 (18) | N1—C2—C3 | 121.9 (6) |
| C1i—Sn1—N2 | 88.48 (19) | N1—C2—H2 | 119.1 |
| N2i—Sn1—N2 | 106.6 (3) | C3—C2—H2 | 119.1 |
| C1—Sn1—N1 | 91.51 (16) | C4—C3—C2 | 119.5 (7) |
| C1i—Sn1—N1 | 92.01 (15) | C4—C3—H3 | 120.2 |
| N2i—Sn1—N1 | 162.09 (16) | C2—C3—H3 | 120.2 |
| N2—Sn1—N1 | 91.30 (17) | C3—C4—C5 | 120.7 (6) |
| C1—Sn1—N1i | 92.01 (15) | C3—C4—H4 | 119.6 |
| C1i—Sn1—N1i | 91.51 (16) | C5—C4—H4 | 119.6 |
| N2i—Sn1—N1i | 91.30 (17) | C4—C5—C6 | 116.9 (6) |
| N2—Sn1—N1i | 162.09 (16) | C4—C5—C7 | 125.6 (6) |
| N1—Sn1—N1i | 70.80 (18) | C6—C5—C7 | 117.6 (7) |
| C2—N1—C6 | 119.4 (4) | N1—C6—C5 | 121.6 (5) |
| C2—N1—Sn1 | 124.2 (3) | N1—C6—C6i | 118.2 (2) |
| C6—N1—Sn1 | 116.4 (3) | C5—C6—C6i | 120.2 (4) |
| C8—N2—Sn1 | 163.6 (5) | C7i—C7—C5 | 122.2 (4) |
| Sn1—C1—H1A | 109.5 | C7i—C7—H7 | 118.9 |
| Sn1—C1—H1B | 109.5 | C5—C7—H7 | 118.9 |
| H1A—C1—H1B | 109.5 | N2—C8—S1 | 178.8 (5) |
| C1—Sn1—N1—C2 | −89.4 (4) | Sn1—N1—C2—C3 | −178.9 (4) |
| C1i—Sn1—N1—C2 | 88.1 (4) | N1—C2—C3—C4 | −0.9 (9) |
| N2i—Sn1—N1—C2 | −179.2 (5) | C2—C3—C4—C5 | 1.4 (10) |
| N2—Sn1—N1—C2 | −0.5 (4) | C3—C4—C5—C6 | −1.1 (9) |
| N1i—Sn1—N1—C2 | 179.0 (4) | C3—C4—C5—C7 | 179.2 (8) |
| C1—Sn1—N1—C6 | 91.6 (3) | C2—N1—C6—C5 | 0.2 (6) |
| C1i—Sn1—N1—C6 | −90.9 (3) | Sn1—N1—C6—C5 | 179.3 (3) |
| N2i—Sn1—N1—C6 | 1.8 (6) | C2—N1—C6—C6i | −178.9 (4) |
| N2—Sn1—N1—C6 | −179.5 (3) | Sn1—N1—C6—C6i | 0.1 (6) |
| N1i—Sn1—N1—C6 | 0.0 (2) | C4—C5—C6—N1 | 0.3 (7) |
| C1—Sn1—N2—C8 | −167.4 (17) | C7—C5—C6—N1 | −180.0 (6) |
| C1i—Sn1—N2—C8 | 9.2 (17) | C4—C5—C6—C6i | 179.4 (5) |
| N2i—Sn1—N2—C8 | −79.3 (17) | C7—C5—C6—C6i | −0.8 (9) |
| N1—Sn1—N2—C8 | 101.1 (17) | C4—C5—C7—C7i | 179.3 (13) |
| N1i—Sn1—N2—C8 | 99.4 (17) | C6—C5—C7—C7i | −0.5 (19) |
| C6—N1—C2—C3 | 0.0 (7) |
| Symmetry code: (i) −x+3/2, −y+1/2, z. |
We thank Shahid Beheshti University and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.
Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
Britton, D. (2006). Acta Cryst. C62, m93–m94.
Najafi, E., Amini, M. M. & Ng, S. W. (2011). Acta Cryst. E67, m350.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.
Few amine adducts of dimethyltin dithiocyanate, which exists as a weakly bridged polymeric chain (Britton, 2006), have been reported. The 4,4'-bipyridine adduct is polymeric (Najafi et al., 2011). In the 1,10-phenanthroline adduct (Scheme I, Fig. 1), the SnIV atom is located on a twofold rotation axis in an octahedral enviroment. The methyl groups are trans to each other whereas the thiocyanate groups are cis to each other.