Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803006056/na6215sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803006056/na6215Isup2.hkl |
CCDC reference: 209896
In an effort to synthesize a macrocyclic tin complex, we added diethyltin dichloride, 2,4-pentanedione, ethylenediamine and sodium diethyl dithiocarbamate trihydrate to DMSO as solvent medium. From the product mixture we isolated suitable single crystals. However, we got an entirely different structure from what we expected.
All H atoms could be located unequivocally by difference Fourier synthesis and were refined with fixed individual displacement parameters [Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl)], using a riding model, with C—H = 0.99 Å or methyl C—H = 0.98 Å. One curious feature of the structure is the very short C15—C16 bond, which at 1.356 (7) Å is much shorter than a usual CH2—CH3 bond. We attribute this to a slight disorder of these atoms. By the way, the structure of Morris & Schlemper (1979) shows the same feature.
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991).
[Sn(CH3)2(C5H10NS2)2] | F(000) = 2712 |
Mr = 445.28 | Dx = 1.477 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 22309 reflections |
a = 27.735 (2) Å | θ = 3.5–25.2° |
b = 12.3703 (7) Å | µ = 1.68 mm−1 |
c = 17.8281 (12) Å | T = 293 K |
β = 100.829 (6)° | Block, colourless |
V = 6007.7 (7) Å3 | 0.22 × 0.21 × 0.12 mm |
Z = 12 |
Stoe IPDS-II two-circle diffractometer | 5755 independent reflections |
Radiation source: fine-focus sealed tube | 3910 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
ω scans | θmax = 25.8°, θmin = 3.6° |
Absorption correction: multi-scan (MULABS; Spek, 1990; Blessing, 1995) | h = −33→33 |
Tmin = 0.708, Tmax = 0.824 | k = −15→15 |
41948 measured reflections | l = −21→21 |
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)] = 0.026 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.052 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.02P)2] where P = (Fo2 + 2Fc2)/3 |
5755 reflections | (Δ/σ)max = 0.004 |
258 parameters | Δρmax = 0.64 e Å−3 |
0 restraints | Δρmin = −0.45 e Å−3 |
[Sn(CH3)2(C5H10NS2)2] | V = 6007.7 (7) Å3 |
Mr = 445.28 | Z = 12 |
Monoclinic, C2/c | Mo Kα radiation |
a = 27.735 (2) Å | µ = 1.68 mm−1 |
b = 12.3703 (7) Å | T = 293 K |
c = 17.8281 (12) Å | 0.22 × 0.21 × 0.12 mm |
β = 100.829 (6)° |
Stoe IPDS-II two-circle diffractometer | 5755 independent reflections |
Absorption correction: multi-scan (MULABS; Spek, 1990; Blessing, 1995) | 3910 reflections with I > 2σ(I) |
Tmin = 0.708, Tmax = 0.824 | Rint = 0.048 |
41948 measured reflections |
R[F2 > 2σ(F2)] = 0.026 | 0 restraints |
wR(F2) = 0.052 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.64 e Å−3 |
5755 reflections | Δρmin = −0.45 e Å−3 |
258 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 | ||
Sn1 | 0.662828 (8) | 0.541443 (16) | 0.400477 (12) | 0.05720 (7) | |
S1 | 0.60531 (3) | 0.38492 (6) | 0.40544 (6) | 0.0693 (2) | |
S2 | 0.55785 (3) | 0.59621 (7) | 0.36857 (6) | 0.0776 (3) | |
S3 | 0.72693 (3) | 0.39578 (6) | 0.43772 (5) | 0.0643 (2) | |
S4 | 0.76803 (3) | 0.60904 (7) | 0.40873 (6) | 0.0754 (2) | |
N1 | 0.50936 (10) | 0.4111 (2) | 0.36286 (16) | 0.0728 (7) | |
N2 | 0.82015 (9) | 0.4268 (2) | 0.43167 (14) | 0.0650 (7) | |
C1 | 0.66556 (15) | 0.6383 (3) | 0.4988 (2) | 0.0979 (13) | |
H1A | 0.6663 | 0.5926 | 0.5426 | 0.147* | |
H1B | 0.6370 | 0.6838 | 0.4924 | 0.147* | |
H1C | 0.6946 | 0.6823 | 0.5062 | 0.147* | |
C2 | 0.66033 (13) | 0.5668 (3) | 0.28242 (19) | 0.0824 (10) | |
H2A | 0.6593 | 0.4983 | 0.2569 | 0.124* | |
H2B | 0.6890 | 0.6059 | 0.2753 | 0.124* | |
H2C | 0.6315 | 0.6077 | 0.2615 | 0.124* | |
C3 | 0.55218 (10) | 0.4619 (3) | 0.37769 (17) | 0.0591 (7) | |
C4 | 0.77714 (10) | 0.4759 (2) | 0.42664 (16) | 0.0555 (7) | |
C5 | 0.50504 (14) | 0.2916 (3) | 0.3642 (3) | 0.0938 (12) | |
H5A | 0.4771 | 0.2698 | 0.3259 | 0.113* | |
H5B | 0.5342 | 0.2601 | 0.3505 | 0.113* | |
C6 | 0.4991 (3) | 0.2488 (4) | 0.4376 (4) | 0.161 (2) | |
H6A | 0.4965 | 0.1715 | 0.4346 | 0.242* | |
H6B | 0.4698 | 0.2782 | 0.4511 | 0.242* | |
H6C | 0.5270 | 0.2685 | 0.4757 | 0.242* | |
C7 | 0.46299 (12) | 0.4720 (3) | 0.3396 (2) | 0.0856 (11) | |
H7A | 0.4390 | 0.4256 | 0.3084 | 0.103* | |
H7B | 0.4689 | 0.5331 | 0.3085 | 0.103* | |
C8 | 0.44229 (16) | 0.5118 (5) | 0.4052 (3) | 0.137 (2) | |
H8A | 0.4123 | 0.5501 | 0.3867 | 0.205* | |
H8B | 0.4654 | 0.5595 | 0.4355 | 0.205* | |
H8C | 0.4358 | 0.4517 | 0.4358 | 0.205* | |
C9 | 0.82803 (12) | 0.3117 (3) | 0.4511 (2) | 0.0747 (9) | |
H9A | 0.8046 | 0.2894 | 0.4823 | 0.090* | |
H9B | 0.8607 | 0.3027 | 0.4813 | 0.090* | |
C10 | 0.82263 (17) | 0.2400 (3) | 0.3824 (3) | 0.1067 (14) | |
H10A | 0.8283 | 0.1663 | 0.3984 | 0.160* | |
H10B | 0.8461 | 0.2608 | 0.3517 | 0.160* | |
H10C | 0.7900 | 0.2469 | 0.3529 | 0.160* | |
C11 | 0.86381 (12) | 0.4851 (3) | 0.4171 (2) | 0.0862 (11) | |
H11A | 0.8535 | 0.5457 | 0.3834 | 0.103* | |
H11B | 0.8832 | 0.4371 | 0.3916 | 0.103* | |
C12 | 0.89494 (16) | 0.5260 (5) | 0.4898 (3) | 0.1310 (18) | |
H12A | 0.9229 | 0.5637 | 0.4782 | 0.197* | |
H12B | 0.9059 | 0.4660 | 0.5229 | 0.197* | |
H12C | 0.8759 | 0.5743 | 0.5148 | 0.197* | |
Sn2 | 0.5000 | 0.08929 (3) | 0.7500 | 0.07005 (11) | |
S5 | 0.43799 (3) | −0.06228 (7) | 0.72285 (6) | 0.0796 (3) | |
S6 | 0.39645 (4) | 0.15789 (8) | 0.70688 (8) | 0.1019 (4) | |
N3 | 0.34354 (11) | −0.0217 (3) | 0.6761 (2) | 0.1022 (11) | |
C13 | 0.49290 (15) | 0.1449 (4) | 0.8595 (2) | 0.1075 (14) | |
H13A | 0.4909 | 0.0842 | 0.8923 | 0.161* | |
H13B | 0.4637 | 0.1878 | 0.8554 | 0.161* | |
H13C | 0.5209 | 0.1881 | 0.8806 | 0.161* | |
C14 | 0.38717 (12) | 0.0231 (3) | 0.6996 (2) | 0.0767 (9) | |
C15 | 0.29574 (19) | 0.0526 (5) | 0.6403 (3) | 0.1252 (16) | |
H15A | 0.3057 | 0.1209 | 0.6211 | 0.150* | |
H15B | 0.2742 | 0.0150 | 0.5994 | 0.150* | |
C16 | 0.2738 (3) | 0.0677 (6) | 0.7013 (4) | 0.199 (3) | |
H16A | 0.2449 | 0.1112 | 0.6865 | 0.298* | |
H16B | 0.2962 | 0.1036 | 0.7412 | 0.298* | |
H16C | 0.2648 | −0.0011 | 0.7195 | 0.298* | |
C17 | 0.33664 (15) | −0.1394 (3) | 0.6673 (3) | 0.1012 (14) | |
H17A | 0.3075 | −0.1528 | 0.6290 | 0.121* | |
H17B | 0.3644 | −0.1694 | 0.6484 | 0.121* | |
C18 | 0.3317 (2) | −0.1970 (4) | 0.7377 (3) | 0.139 (2) | |
H18A | 0.3272 | −0.2728 | 0.7270 | 0.208* | |
H18B | 0.3038 | −0.1695 | 0.7563 | 0.208* | |
H18C | 0.3608 | −0.1863 | 0.7756 | 0.208* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.05827 (12) | 0.04909 (12) | 0.06721 (13) | −0.00293 (10) | 0.01937 (9) | −0.00405 (11) |
S1 | 0.0511 (4) | 0.0508 (5) | 0.1068 (7) | 0.0005 (3) | 0.0168 (4) | 0.0055 (4) |
S2 | 0.0693 (5) | 0.0584 (5) | 0.1088 (7) | 0.0109 (4) | 0.0261 (5) | 0.0077 (5) |
S3 | 0.0535 (4) | 0.0523 (5) | 0.0887 (6) | −0.0057 (3) | 0.0177 (4) | 0.0055 (4) |
S4 | 0.0707 (5) | 0.0556 (5) | 0.1026 (7) | −0.0126 (4) | 0.0233 (5) | 0.0037 (5) |
N1 | 0.0582 (16) | 0.0772 (19) | 0.085 (2) | −0.0004 (14) | 0.0182 (14) | −0.0012 (15) |
N2 | 0.0527 (15) | 0.0768 (18) | 0.0679 (17) | −0.0022 (12) | 0.0178 (12) | 0.0115 (14) |
C1 | 0.092 (3) | 0.100 (3) | 0.107 (3) | −0.014 (2) | 0.030 (2) | −0.048 (2) |
C2 | 0.079 (2) | 0.099 (3) | 0.073 (2) | 0.0057 (19) | 0.0216 (17) | 0.011 (2) |
C3 | 0.0523 (16) | 0.0603 (18) | 0.0673 (19) | −0.0004 (15) | 0.0182 (14) | −0.0011 (16) |
C4 | 0.0551 (17) | 0.0582 (19) | 0.0550 (18) | −0.0071 (14) | 0.0152 (13) | 0.0012 (14) |
C5 | 0.073 (2) | 0.087 (3) | 0.125 (4) | −0.012 (2) | 0.028 (2) | −0.016 (3) |
C6 | 0.197 (6) | 0.115 (4) | 0.196 (6) | −0.010 (4) | 0.102 (5) | 0.038 (4) |
C7 | 0.0535 (19) | 0.110 (3) | 0.091 (3) | 0.0104 (19) | 0.0076 (17) | 0.005 (2) |
C8 | 0.087 (3) | 0.215 (6) | 0.117 (4) | 0.056 (3) | 0.042 (3) | 0.016 (4) |
C9 | 0.066 (2) | 0.079 (2) | 0.082 (3) | 0.0135 (17) | 0.0203 (17) | 0.023 (2) |
C10 | 0.128 (4) | 0.087 (3) | 0.116 (4) | 0.024 (2) | 0.051 (3) | 0.004 (3) |
C11 | 0.0566 (19) | 0.107 (3) | 0.101 (3) | −0.0086 (19) | 0.0282 (19) | 0.017 (2) |
C12 | 0.085 (3) | 0.159 (5) | 0.142 (4) | −0.041 (3) | 0.004 (3) | 0.005 (4) |
Sn2 | 0.0666 (2) | 0.05157 (18) | 0.1002 (3) | 0.000 | 0.03682 (18) | 0.000 |
S5 | 0.0719 (6) | 0.0531 (5) | 0.1127 (7) | −0.0004 (4) | 0.0149 (5) | −0.0077 (5) |
S6 | 0.0725 (6) | 0.0626 (6) | 0.1785 (12) | 0.0098 (4) | 0.0442 (7) | −0.0050 (6) |
N3 | 0.0624 (18) | 0.086 (2) | 0.163 (3) | −0.0019 (16) | 0.0335 (19) | −0.030 (2) |
C13 | 0.091 (3) | 0.114 (3) | 0.129 (4) | −0.035 (2) | 0.052 (3) | −0.045 (3) |
C14 | 0.066 (2) | 0.070 (2) | 0.100 (3) | 0.0009 (17) | 0.0327 (18) | −0.0111 (19) |
C15 | 0.124 (4) | 0.155 (5) | 0.101 (3) | −0.013 (3) | 0.035 (3) | −0.014 (3) |
C16 | 0.239 (8) | 0.221 (8) | 0.166 (6) | −0.043 (6) | 0.114 (6) | −0.039 (6) |
C17 | 0.083 (3) | 0.100 (3) | 0.129 (4) | −0.027 (2) | 0.040 (2) | −0.052 (3) |
C18 | 0.177 (5) | 0.104 (4) | 0.158 (5) | −0.061 (3) | 0.089 (4) | −0.059 (3) |
Sn1—C1 | 2.113 (3) | C9—H9B | 0.9700 |
Sn1—C2 | 2.116 (3) | C10—H10A | 0.9600 |
Sn1—S1 | 2.5207 (8) | C10—H10B | 0.9600 |
Sn1—S3 | 2.5308 (8) | C10—H10C | 0.9600 |
S1—C3 | 1.746 (3) | C11—C12 | 1.504 (5) |
S2—C3 | 1.680 (3) | C11—H11A | 0.9700 |
S3—C4 | 1.750 (3) | C11—H11B | 0.9700 |
S4—C4 | 1.688 (3) | C12—H12A | 0.9600 |
N1—C3 | 1.326 (4) | C12—H12B | 0.9600 |
N1—C5 | 1.483 (4) | C12—H12C | 0.9600 |
N1—C7 | 1.481 (4) | Sn2—C13i | 2.114 (4) |
N2—C4 | 1.326 (4) | Sn2—C13 | 2.114 (4) |
N2—C9 | 1.472 (4) | Sn2—S5i | 2.5287 (9) |
N2—C11 | 1.474 (4) | Sn2—S5 | 2.5287 (9) |
C1—H1A | 0.9600 | S5—C14 | 1.748 (3) |
C1—H1B | 0.9600 | S6—C14 | 1.688 (4) |
C1—H1C | 0.9600 | N3—C14 | 1.325 (4) |
C2—H2A | 0.9600 | N3—C17 | 1.473 (5) |
C2—H2B | 0.9600 | N3—C15 | 1.641 (6) |
C2—H2C | 0.9600 | C13—H13A | 0.9600 |
C5—C6 | 1.449 (6) | C13—H13B | 0.9600 |
C5—H5A | 0.9700 | C13—H13C | 0.9600 |
C5—H5B | 0.9700 | C15—C16 | 1.356 (7) |
C6—H6A | 0.9600 | C15—H15A | 0.9700 |
C6—H6B | 0.9600 | C15—H15B | 0.9700 |
C6—H6C | 0.9600 | C16—H16A | 0.9600 |
C7—C8 | 1.480 (5) | C16—H16B | 0.9600 |
C7—H7A | 0.9700 | C16—H16C | 0.9600 |
C7—H7B | 0.9700 | C17—C18 | 1.471 (6) |
C8—H8A | 0.9600 | C17—H17A | 0.9700 |
C8—H8B | 0.9600 | C17—H17B | 0.9700 |
C8—H8C | 0.9600 | C18—H18A | 0.9600 |
C9—C10 | 1.498 (5) | C18—H18B | 0.9600 |
C9—H9A | 0.9700 | C18—H18C | 0.9600 |
C1—Sn1—C2 | 136.95 (17) | C9—C10—H10A | 109.5 |
C1—Sn1—S1 | 109.30 (12) | C9—C10—H10B | 109.5 |
C2—Sn1—S1 | 104.24 (11) | H10A—C10—H10B | 109.5 |
C1—Sn1—S3 | 105.78 (13) | C9—C10—H10C | 109.5 |
C2—Sn1—S3 | 104.86 (10) | H10A—C10—H10C | 109.5 |
S1—Sn1—S3 | 82.06 (3) | H10B—C10—H10C | 109.5 |
C3—S1—Sn1 | 94.44 (10) | N2—C11—C12 | 111.7 (3) |
C4—S3—Sn1 | 95.85 (10) | N2—C11—H11A | 109.3 |
C3—N1—C5 | 122.7 (3) | C12—C11—H11A | 109.3 |
C3—N1—C7 | 120.9 (3) | N2—C11—H11B | 109.3 |
C5—N1—C7 | 116.3 (3) | C12—C11—H11B | 109.3 |
C4—N2—C9 | 123.4 (2) | H11A—C11—H11B | 107.9 |
C4—N2—C11 | 121.5 (3) | C11—C12—H12A | 109.5 |
C9—N2—C11 | 115.1 (3) | C11—C12—H12B | 109.5 |
Sn1—C1—H1A | 109.5 | H12A—C12—H12B | 109.5 |
Sn1—C1—H1B | 109.5 | C11—C12—H12C | 109.5 |
H1A—C1—H1B | 109.5 | H12A—C12—H12C | 109.5 |
Sn1—C1—H1C | 109.5 | H12B—C12—H12C | 109.5 |
H1A—C1—H1C | 109.5 | C13i—Sn2—C13 | 142.0 (3) |
H1B—C1—H1C | 109.5 | C13i—Sn2—S5i | 103.90 (11) |
Sn1—C2—H2A | 109.5 | C13—Sn2—S5i | 104.04 (14) |
Sn1—C2—H2B | 109.5 | C13i—Sn2—S5 | 104.04 (14) |
H2A—C2—H2B | 109.5 | C13—Sn2—S5 | 103.90 (11) |
Sn1—C2—H2C | 109.5 | S5i—Sn2—S5 | 84.29 (4) |
H2A—C2—H2C | 109.5 | C14—S5—Sn2 | 94.96 (12) |
H2B—C2—H2C | 109.5 | C14—N3—C17 | 122.7 (3) |
N1—C3—S2 | 123.1 (2) | C14—N3—C15 | 120.7 (3) |
N1—C3—S1 | 118.4 (2) | C17—N3—C15 | 115.7 (3) |
S2—C3—S1 | 118.51 (17) | Sn2—C13—H13A | 109.5 |
N2—C4—S4 | 124.1 (2) | Sn2—C13—H13B | 109.5 |
N2—C4—S3 | 117.3 (2) | H13A—C13—H13B | 109.5 |
S4—C4—S3 | 118.67 (17) | Sn2—C13—H13C | 109.5 |
C6—C5—N1 | 113.7 (4) | H13A—C13—H13C | 109.5 |
C6—C5—H5A | 108.8 | H13B—C13—H13C | 109.5 |
N1—C5—H5A | 108.8 | N3—C14—S6 | 123.7 (3) |
C6—C5—H5B | 108.8 | N3—C14—S5 | 118.0 (3) |
N1—C5—H5B | 108.8 | S6—C14—S5 | 118.3 (2) |
H5A—C5—H5B | 107.7 | C16—C15—N3 | 102.5 (5) |
C5—C6—H6A | 109.5 | C16—C15—H15A | 111.3 |
C5—C6—H6B | 109.5 | N3—C15—H15A | 111.3 |
H6A—C6—H6B | 109.5 | C16—C15—H15B | 111.3 |
C5—C6—H6C | 109.5 | N3—C15—H15B | 111.3 |
H6A—C6—H6C | 109.5 | H15A—C15—H15B | 109.2 |
H6B—C6—H6C | 109.5 | C15—C16—H16A | 109.5 |
N1—C7—C8 | 113.2 (3) | C15—C16—H16B | 109.5 |
N1—C7—H7A | 108.9 | H16A—C16—H16B | 109.5 |
C8—C7—H7A | 108.9 | C15—C16—H16C | 109.5 |
N1—C7—H7B | 108.9 | H16A—C16—H16C | 109.5 |
C8—C7—H7B | 108.9 | H16B—C16—H16C | 109.5 |
H7A—C7—H7B | 107.7 | C18—C17—N3 | 114.8 (4) |
C7—C8—H8A | 109.5 | C18—C17—H17A | 108.6 |
C7—C8—H8B | 109.5 | N3—C17—H17A | 108.6 |
H8A—C8—H8B | 109.5 | C18—C17—H17B | 108.6 |
C7—C8—H8C | 109.5 | N3—C17—H17B | 108.6 |
H8A—C8—H8C | 109.5 | H17A—C17—H17B | 107.6 |
H8B—C8—H8C | 109.5 | C17—C18—H18A | 109.5 |
N2—C9—C10 | 113.1 (3) | C17—C18—H18B | 109.5 |
N2—C9—H9A | 109.0 | H18A—C18—H18B | 109.5 |
C10—C9—H9A | 109.0 | C17—C18—H18C | 109.5 |
N2—C9—H9B | 109.0 | H18A—C18—H18C | 109.5 |
C10—C9—H9B | 109.0 | H18B—C18—H18C | 109.5 |
H9A—C9—H9B | 107.8 | ||
C1—Sn1—S1—C3 | 77.56 (17) | C3—N1—C7—C8 | −86.2 (5) |
C2—Sn1—S1—C3 | −75.03 (14) | C5—N1—C7—C8 | 97.0 (4) |
S3—Sn1—S1—C3 | −178.43 (10) | C4—N2—C9—C10 | 93.7 (4) |
C1—Sn1—S3—C4 | −80.37 (15) | C11—N2—C9—C10 | −85.8 (4) |
C2—Sn1—S3—C4 | 69.02 (15) | C4—N2—C11—C12 | 95.4 (4) |
S1—Sn1—S3—C4 | 171.73 (10) | C9—N2—C11—C12 | −85.2 (4) |
C5—N1—C3—S2 | 174.3 (3) | C13i—Sn2—S5—C14 | −76.46 (16) |
C7—N1—C3—S2 | −2.3 (4) | C13—Sn2—S5—C14 | 77.52 (19) |
C5—N1—C3—S1 | −3.9 (4) | S5i—Sn2—S5—C14 | −179.40 (13) |
C7—N1—C3—S1 | 179.5 (2) | C17—N3—C14—S6 | 177.5 (3) |
Sn1—S1—C3—N1 | 172.3 (2) | C15—N3—C14—S6 | 8.9 (5) |
Sn1—S1—C3—S2 | −5.91 (18) | C17—N3—C14—S5 | −1.5 (5) |
C9—N2—C4—S4 | 176.8 (2) | C15—N3—C14—S5 | −170.1 (3) |
C11—N2—C4—S4 | −3.8 (4) | Sn2—S5—C14—N3 | 176.5 (3) |
C9—N2—C4—S3 | −4.4 (4) | Sn2—S5—C14—S6 | −2.6 (2) |
C11—N2—C4—S3 | 175.0 (2) | C14—N3—C15—C16 | −96.8 (6) |
Sn1—S3—C4—N2 | −171.8 (2) | C17—N3—C15—C16 | 93.8 (5) |
Sn1—S3—C4—S4 | 7.04 (18) | C14—N3—C17—C18 | 85.0 (5) |
C3—N1—C5—C6 | 91.9 (5) | C15—N3—C17—C18 | −105.8 (5) |
C7—N1—C5—C6 | −91.4 (5) |
Symmetry code: (i) −x+1, y, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | [Sn(CH3)2(C5H10NS2)2] |
Mr | 445.28 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 27.735 (2), 12.3703 (7), 17.8281 (12) |
β (°) | 100.829 (6) |
V (Å3) | 6007.7 (7) |
Z | 12 |
Radiation type | Mo Kα |
µ (mm−1) | 1.68 |
Crystal size (mm) | 0.22 × 0.21 × 0.12 |
Data collection | |
Diffractometer | Stoe IPDS-II two-circle diffractometer |
Absorption correction | Multi-scan (MULABS; Spek, 1990; Blessing, 1995) |
Tmin, Tmax | 0.708, 0.824 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 41948, 5755, 3910 |
Rint | 0.048 |
(sin θ/λ)max (Å−1) | 0.613 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.026, 0.052, 0.97 |
No. of reflections | 5755 |
No. of parameters | 258 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.64, −0.45 |
Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991).
Sn1—C1 | 2.113 (3) | S3—C4 | 1.750 (3) |
Sn1—C2 | 2.116 (3) | S4—C4 | 1.688 (3) |
Sn1—S1 | 2.5207 (8) | Sn2—C13 | 2.114 (4) |
Sn1—S3 | 2.5308 (8) | S5—C14 | 1.748 (3) |
S1—C3 | 1.746 (3) | S6—C14 | 1.688 (4) |
S2—C3 | 1.680 (3) |
Perspective views of the title compound, (I), are shown in Figs. 1 and 2. The original structure was reported by Morris & Schlemper (1979), who also reported a triclinic polymorph. Lockhart et al. (1986), on the other hand, had determined the structure of an orthorhombic polymorph. The geometric parameters of both determinations agree quite well. A least-squares fit between all non-H atoms gives an r.m.s. deviation of 0.044 Å. However, the present work is of significantly improved precision and we were able to determine the positions of the H atoms. There are one and a half molecules in the asymmetric unit. The Sn atom of one molecule is located on a twofold rotation axis, whereas all other atoms are located on general positions.