Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680400488X/na6299sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680400488X/na6299Isup2.hkl |
CCDC reference: 238628
Data collection: COLLECT (Nonius, 1999); cell refinement: EVALCCD (Duisenberg et al., 2003); data reduction: EVALCCD; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
[Ge(CH3)2(C4N2S2)] | F(000) = 960 |
Mr = 242.88 | Dx = 1.720 Mg m−3 |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 116 reflections |
a = 25.1259 (19) Å | θ = 6.0–20.0° |
b = 9.9284 (8) Å | µ = 3.65 mm−1 |
c = 7.5207 (4) Å | T = 294 K |
V = 1876.1 (2) Å3 | Block, colourless |
Z = 8 | 0.18 × 0.08 × 0.07 mm |
Nonius KappaCCD area-detector diffractometer | 2452 independent reflections |
Radiation source: fine-focus sealed tube | 1413 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
Detector resolution: 9 pixels mm-1 | θmax = 28.5°, θmin = 3.8° |
φ and ω scans, with 1.20° and 72 sec per frame | h = −33→33 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | k = −13→13 |
Tmin = 0.560, Tmax = 0.784 | l = −9→9 |
25208 measured reflections |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.073 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0252P)2 + 0.922P] where P = (Fo2 + 2Fc2)/3 |
2452 reflections | (Δ/σ)max < 0.001 |
123 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.74 e Å−3 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
Ge1A | 0.01711 (2) | 0.25000 | 0.74728 (6) | 0.0361 (2) | |
S1A | −0.05273 (3) | 0.39625 (9) | 0.71970 (12) | 0.0379 (3) | |
N1A | −0.18946 (12) | 0.0280 (4) | 0.5604 (4) | 0.0570 (12) | |
C1A | 0.0495 (3) | 0.25000 | 0.9806 (8) | 0.059 (3) | |
C2A | 0.0578 (2) | 0.25000 | 0.5298 (7) | 0.051 (2) | |
C3A | −0.08898 (16) | 0.25000 | 0.6834 (6) | 0.0293 (17) | |
C4A | −0.14102 (17) | 0.25000 | 0.6259 (6) | 0.0317 (16) | |
C5A | −0.16808 (13) | 0.1271 (4) | 0.5904 (4) | 0.0363 (13) | |
Ge1B | 0.23253 (2) | 0.25000 | 0.44324 (6) | 0.0359 (2) | |
S1B | 0.30243 (3) | 0.39597 (9) | 0.41857 (12) | 0.0386 (3) | |
N1B | 0.44077 (13) | 0.0279 (4) | 0.2725 (4) | 0.0623 (16) | |
C1B | 0.2023 (2) | 0.25000 | 0.6756 (7) | 0.0433 (19) | |
C2B | 0.1915 (3) | 0.25000 | 0.2259 (7) | 0.058 (3) | |
C3B | 0.33876 (17) | 0.25000 | 0.3857 (5) | 0.0270 (16) | |
C4B | 0.39175 (17) | 0.25000 | 0.3320 (6) | 0.0323 (17) | |
C5B | 0.41915 (13) | 0.1265 (4) | 0.3006 (4) | 0.0381 (14) | |
H1 | 0.02190 | 0.25000 | 1.06880 | 0.31 (8)* | |
H2 | 0.07120 | 0.32880 | 0.99460 | 0.22 (3)* | |
H7 | 0.03380 | 0.25000 | 0.43090 | 0.13 (3)* | |
H8 | 0.07980 | 0.17110 | 0.52480 | 0.097 (16)* | |
H4 | 0.23060 | 0.25000 | 0.76130 | 0.08 (2)* | |
H5 | 0.18080 | 0.17110 | 0.69150 | 0.13 (2)* | |
H10 | 0.21520 | 0.25000 | 0.12610 | 0.16 (4)* | |
H11 | 0.16950 | 0.32880 | 0.22180 | 0.15 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ge1A | 0.0283 (3) | 0.0443 (4) | 0.0358 (3) | 0.0000 | −0.0060 (2) | 0.0000 |
S1A | 0.0364 (5) | 0.0255 (5) | 0.0517 (6) | −0.0025 (4) | −0.0092 (4) | −0.0017 (4) |
N1A | 0.051 (2) | 0.061 (2) | 0.059 (2) | −0.0219 (19) | −0.0025 (15) | −0.0089 (17) |
C1A | 0.063 (4) | 0.068 (5) | 0.046 (4) | 0.0000 | −0.036 (3) | 0.0000 |
C2A | 0.044 (3) | 0.062 (4) | 0.046 (4) | 0.0000 | 0.007 (3) | 0.0000 |
C3A | 0.029 (3) | 0.030 (3) | 0.029 (3) | 0.0000 | −0.001 (2) | 0.0000 |
C4A | 0.025 (2) | 0.035 (3) | 0.035 (3) | 0.0000 | −0.002 (2) | 0.0000 |
C5A | 0.0259 (18) | 0.048 (3) | 0.035 (2) | −0.0056 (18) | 0.0012 (14) | 0.0003 (16) |
Ge1B | 0.0287 (3) | 0.0456 (4) | 0.0334 (3) | 0.0000 | −0.0011 (2) | 0.0000 |
S1B | 0.0380 (6) | 0.0262 (5) | 0.0516 (6) | 0.0034 (4) | 0.0047 (4) | 0.0015 (4) |
N1B | 0.057 (2) | 0.061 (3) | 0.069 (3) | 0.022 (2) | 0.0079 (17) | −0.0100 (18) |
C1B | 0.037 (3) | 0.049 (4) | 0.044 (3) | 0.0000 | 0.001 (3) | 0.0000 |
C2B | 0.070 (4) | 0.061 (5) | 0.042 (4) | 0.0000 | −0.020 (3) | 0.0000 |
C3B | 0.032 (3) | 0.027 (3) | 0.022 (2) | 0.0000 | −0.002 (2) | 0.0000 |
C4B | 0.033 (3) | 0.039 (3) | 0.025 (3) | 0.0000 | −0.002 (2) | 0.0000 |
C5B | 0.034 (2) | 0.044 (3) | 0.0364 (19) | −0.0001 (18) | 0.0043 (16) | −0.0016 (17) |
Ge1A—S1A | 2.2871 (9) | C1A—H2 | 0.9594 |
Ge1A—C1A | 1.934 (6) | C1A—H1 | 0.9596 |
Ge1A—C2A | 1.929 (5) | C1A—H2i | 0.9594 |
Ge1A—S1Ai | 2.2871 (9) | C2A—H8i | 0.9595 |
Ge1B—S1Bi | 2.2846 (9) | C2A—H7 | 0.9575 |
Ge1B—S1B | 2.2846 (9) | C2A—H8 | 0.9595 |
Ge1B—C1B | 1.905 (5) | C3B—C4B | 1.391 (6) |
Ge1B—C2B | 1.933 (6) | C4B—C5B | 1.426 (4) |
S1A—C3A | 1.736 (2) | C4B—C5Bi | 1.426 (4) |
S1B—C3B | 1.731 (2) | C1B—H4 | 0.9597 |
N1A—C5A | 1.144 (5) | C1B—H5 | 0.9590 |
N1B—C5B | 1.139 (5) | C1B—H5i | 0.9590 |
C3A—C4A | 1.377 (6) | C2B—H10 | 0.9581 |
C4A—C5A | 1.422 (4) | C2B—H11 | 0.9584 |
C4A—C5Ai | 1.422 (4) | C2B—H11i | 0.9584 |
Ge1A···N1Bii | 2.961 (4) | C1A···N1Biii | 3.182 (5) |
Ge1A···N1Biii | 2.961 (4) | C1A···S1Ai | 3.544 (6) |
Ge1B···N1Aiv | 2.965 (4) | C1B···N1Av | 3.297 (5) |
Ge1B···N1Av | 2.965 (4) | C1B···S1Bi | 3.488 (5) |
S1A···C1A | 3.544 (6) | C1B···N1Aiv | 3.297 (5) |
S1A···N1Biii | 3.127 (3) | C1B···S1B | 3.488 (5) |
S1A···S1Ai | 2.9041 (13) | C1B···C2B | 3.393 (7) |
S1A···C5Bvi | 3.683 (3) | C2A···N1Bii | 3.308 (5) |
S1A···C2A | 3.444 (5) | C2A···N1Biii | 3.308 (5) |
S1B···S1Bi | 2.8985 (13) | C2A···S1Ai | 3.444 (5) |
S1B···N1Aiv | 3.131 (3) | C2A···S1A | 3.444 (5) |
S1B···C1B | 3.488 (5) | C2A···C1A | 3.397 (8) |
S1B···C2B | 3.460 (7) | C2B···N1Av | 3.194 (5) |
N1A···C2Bvii | 3.194 (5) | C2B···S1B | 3.460 (7) |
N1A···S1Bvii | 3.131 (3) | C2B···C1B | 3.393 (7) |
N1A···C1Bvii | 3.297 (5) | C2B···S1Bi | 3.460 (7) |
N1A···Ge1Bvii | 2.965 (4) | C2B···N1Aiv | 3.194 (5) |
N1A···C1Bv | 3.297 (5) | C4A···C4Bx | 3.541 (6) |
N1A···C2Bv | 3.194 (5) | C4A···C4Bxi | 3.541 (6) |
N1A···Ge1Bv | 2.965 (4) | C4B···C4Axii | 3.541 (6) |
N1B···C2Aviii | 3.308 (5) | C4B···C4Axiii | 3.541 (6) |
N1B···Ge1Aviii | 2.961 (4) | C5B···S1Axiv | 3.683 (3) |
N1B···C1Aix | 3.182 (5) | C5A···H4xv | 3.0354 |
N1B···C2Aix | 3.308 (5) | C5A···H4vi | 3.0354 |
N1B···S1Aix | 3.127 (3) | C5B···H1xvi | 3.0221 |
N1B···C1Aviii | 3.182 (5) | C5B···H1xiv | 3.0221 |
N1B···Ge1Aix | 2.961 (4) | H1···C5Bxv | 3.0221 |
N1A···H5v | 2.7466 | H1···C5Bvi | 3.0221 |
N1A···H11vii | 2.6165 | H2···N1Biii | 2.6054 |
N1B···H8viii | 2.7642 | H4···C5Axiv | 3.0354 |
N1B···H2ix | 2.6054 | H4···C5Axvi | 3.0354 |
C1A···N1Bii | 3.182 (5) | H5···N1Av | 2.7466 |
C1A···S1A | 3.544 (6) | H8···N1Bii | 2.7642 |
C1A···C2A | 3.397 (8) | H11···N1Aiv | 2.6165 |
S1A—Ge1A—C1A | 113.90 (16) | H2—C1A—H2i | 109.27 |
S1A—Ge1A—C2A | 109.26 (12) | Ge1A—C2A—H7 | 108.96 |
S1A—Ge1A—S1Ai | 78.82 (3) | Ge1A—C2A—H8 | 109.79 |
C1A—Ge1A—C2A | 123.1 (3) | Ge1A—C2A—H8i | 109.79 |
S1Ai—Ge1A—C1A | 113.90 (16) | H7—C2A—H8 | 109.41 |
S1Ai—Ge1A—C2A | 109.26 (12) | H7—C2A—H8i | 109.41 |
S1B—Ge1B—S1Bi | 78.75 (3) | H8—C2A—H8i | 109.46 |
C1B—Ge1B—C2B | 124.3 (3) | S1B—C3B—C4B | 123.11 (12) |
S1Bi—Ge1B—C1B | 112.39 (11) | S1B—C3B—S1Bi | 113.8 (2) |
S1Bi—Ge1B—C2B | 109.96 (16) | S1Bi—C3B—C4B | 123.11 (12) |
S1B—Ge1B—C1B | 112.39 (11) | C3B—C4B—C5B | 120.7 (2) |
S1B—Ge1B—C2B | 109.96 (16) | C3B—C4B—C5Bi | 120.7 (2) |
Ge1A—S1A—C3A | 83.44 (12) | C5B—C4B—C5Bi | 118.6 (4) |
Ge1B—S1B—C3B | 83.45 (12) | N1B—C5B—C4B | 178.8 (4) |
S1A—C3A—C4A | 123.20 (12) | Ge1B—C1B—H4 | 108.70 |
S1A—C3A—S1Ai | 113.6 (2) | Ge1B—C1B—H5 | 109.81 |
S1Ai—C3A—C4A | 123.20 (12) | Ge1B—C1B—H5i | 109.81 |
C3A—C4A—C5A | 120.9 (2) | H4—C1B—H5 | 109.49 |
C3A—C4A—C5Ai | 120.9 (2) | H4—C1B—H5i | 109.49 |
C5A—C4A—C5Ai | 118.2 (4) | H5—C1B—H5i | 109.53 |
N1A—C5A—C4A | 179.3 (4) | Ge1B—C2B—H10 | 109.33 |
H1—C1A—H2i | 109.56 | Ge1B—C2B—H11 | 109.57 |
Ge1A—C1A—H1 | 108.85 | Ge1B—C2B—H11i | 109.57 |
Ge1A—C1A—H2 | 109.80 | H10—C2B—H11 | 109.47 |
Ge1A—C1A—H2i | 109.80 | H10—C2B—H11i | 109.47 |
H1—C1A—H2 | 109.56 | H11—C2B—H11i | 109.43 |
C1A—Ge1A—S1A—C3A | −116.8 (2) | Ge1A—S1A—C3A—C4A | −170.4 (4) |
C2A—Ge1A—S1A—C3A | 101.22 (19) | Ge1B—S1B—C3B—S1Bi | −7.09 (18) |
S1Ai—Ge1A—S1A—C3A | −5.46 (15) | Ge1B—S1Bi—C3B—S1B | 7.09 (18) |
S1A—Ge1A—S1Ai—C3A | 5.46 (15) | Ge1B—S1B—C3B—C4B | 170.9 (4) |
S1Bi—Ge1B—S1B—C3B | 5.00 (13) | S1A—C3A—C4A—C5A | 177.1 (3) |
C1B—Ge1B—S1B—C3B | 114.76 (17) | S1Ai—C3A—C4A—C5A | −0.8 (6) |
C2B—Ge1B—S1B—C3B | −102.3 (2) | S1A—C3A—C4A—C5Ai | 0.8 (6) |
S1B—Ge1B—S1Bi—C3B | −5.00 (13) | S1Bi—C3B—C4B—C5B | 0.1 (6) |
Ge1A—S1A—C3A—S1Ai | 7.7 (2) | S1B—C3B—C4B—C5Bi | −0.1 (6) |
Ge1A—S1Ai—C3A—S1A | −7.7 (2) | S1B—C3B—C4B—C5B | −177.7 (3) |
Symmetry codes: (i) x, −y+1/2, z; (ii) −x+1/2, −y, z+1/2; (iii) −x+1/2, y+1/2, z+1/2; (iv) −x, y+1/2, −z+1; (v) −x, −y, −z+1; (vi) x−1/2, −y+1/2, −z+3/2; (vii) −x, y−1/2, −z+1; (viii) −x+1/2, −y, z−1/2; (ix) −x+1/2, y−1/2, z−1/2; (x) x−1/2, −y+1/2, −z+1/2; (xi) x−1/2, y, −z+1/2; (xii) x+1/2, −y+1/2, −z+1/2; (xiii) x+1/2, y, −z+1/2; (xiv) x+1/2, −y+1/2, −z+3/2; (xv) x−1/2, y, −z+3/2; (xvi) x+1/2, y, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1A—H2···N1Biii | 0.96 | 2.61 | 3.182 (5) | 119 |
C2B—H11···N1Aiv | 0.96 | 2.62 | 3.194 (5) | 119 |
Symmetry codes: (iii) −x+1/2, y+1/2, z+1/2; (iv) −x, y+1/2, −z+1. |