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The title mol­ecule, [Ge(CH3O)2(C4N2S2)], exhibits a non-planar geometry and the Ge atom is coordinated by two S and the O atoms of two methoxy groups. The five-membered ring adopts an envelope conformation. A mirror plane passes through the Ge atom, the methoxy groups and the mid-point of the C=C bond.

Supporting information


Crystallographic Information File (CIF)
Contains datablocks global, I


Structure factor file (CIF format)
Contains datablock I

CCDC reference: 226655

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • R factor = 0.037
  • wR factor = 0.101
  • Data-to-parameter ratio = 21.9

checkCIF/PLATON results

No syntax errors found

Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.94
Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Ge1 - O1 = 10.03 su PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Ge1 - O2 = 10.41 su PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... Ge1
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 28.30 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 1469 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 1569 Completeness (_total/calc) 93.63% PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C3 = 5.82 su PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O1 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C2 = 1.42 Ang.
1 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 4 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 6 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

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens,1996); data reduction: SAINT; 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).

2,2-Dimethoxy-1,3,2-dithiagermole-4,5-dicarbonitrile top
Crystal data top
[Ge(CH3O)2(C4N2S2)]F(000) = 536
Mr = 272.86Dx = 1.519 Mg m3
Orthorhombic, PnnmMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2 2nCell parameters from 3800 reflections
a = 12.2960 (8) Åθ = 5.3–56.1°
b = 9.7463 (7) ŵ = 2.89 mm1
c = 9.9583 (7) ÅT = 293 K
V = 1193.41 (14) Å3Block, colourless
Z = 40.40 × 0.36 × 0.28 mm
Data collection top
Siemens SMART CCD area-detector
1469 independent reflections
Radiation source: fine-focus sealed tube1230 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 2.6°
ω scansh = 1611
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1012
Tmin = 0.350, Tmax = 0.445l = 1313
6631 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters not refined
S = 1.03 w = 1/[σ2(Fo2) + (0.053P)2 + 0.6463P]
where P = (Fo2 + 2Fc2)/3
1469 reflections(Δ/σ)max < 0.001
67 parametersΔρmax = 0.78 e Å3
0 restraintsΔρmin = 0.51 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ge10.21928 (3)0.32621 (4)0.000000.0555 (2)
S10.34029 (7)0.28757 (11)0.16743 (7)0.0702 (3)
O10.1713 (5)0.5164 (5)0.000000.1117 (19)
O20.1122 (4)0.1806 (4)0.000000.1033 (17)
N10.6082 (3)0.1297 (4)0.2018 (3)0.0848 (10)
C10.4460 (2)0.2246 (3)0.0685 (3)0.0557 (8)
C20.5368 (2)0.1712 (3)0.1405 (3)0.0632 (9)
C30.2578 (8)0.6156 (7)0.000000.114 (3)
C40.1590 (7)0.0422 (7)0.000000.139 (4)
Atomic displacement parameters (Å2) top
Ge10.0519 (3)0.0617 (3)0.0530 (3)0.0043 (2)0.00000.0000
S10.0631 (4)0.1076 (6)0.0398 (3)0.0034 (4)0.0031 (3)0.0026 (3)
O10.136 (4)0.093 (3)0.106 (3)0.001 (3)0.00000.0000
O20.094 (3)0.109 (3)0.107 (3)0.018 (2)0.00000.0000
N10.0646 (16)0.116 (2)0.0739 (18)0.0046 (16)0.0153 (14)0.0137 (17)
C10.0480 (13)0.0760 (15)0.0432 (12)0.0080 (12)0.0005 (10)0.0004 (11)
C20.0546 (14)0.0857 (19)0.0493 (13)0.0146 (13)0.0035 (12)0.0030 (12)
C30.136 (6)0.078 (4)0.129 (6)0.029 (4)0.00000.0000
C40.096 (5)0.077 (4)0.245 (11)0.027 (4)0.00000.0000
Geometric parameters (Å, º) top
Ge1—S12.2662 (8)C1—C21.425 (4)
Ge1—O11.945 (5)C1—C1i1.364 (4)
Ge1—O21.936 (4)C3—H3A0.9593
Ge1—S1i2.2662 (8)C3—H3B0.9602
S1—C11.743 (3)C3—H3Bi0.9602
O1—C31.437 (10)C4—H4A0.9594
O2—C41.467 (8)C4—H4B0.9603
N1—C21.143 (4)C4—H4Bi0.9603
Ge1···N1ii3.297 (3)C2···C3viii3.557 (8)
Ge1···N1iii3.297 (3)C3···C2viii3.557 (8)
S1···N1ii3.239 (4)C3···C2vii3.557 (8)
N1···Ge1iv3.297 (3)H3B···C2vii3.0165
N1···S1iv3.239 (4)H4A···H4Aix2.5233
N1···Ge1v3.297 (3)H4A···H4Ax2.5233
C2···C2vi3.458 (4)H4B···S1i3.1554
C2···C3vii3.557 (8)
S1—Ge1—O1110.95 (11)O1—C3—H3A108.54
S1—Ge1—O2108.95 (9)O1—C3—H3B109.94
S1—Ge1—S1i94.74 (3)O1—C3—H3Bi109.94
O1—Ge1—O2119.5 (2)H3A—C3—H3B109.50
S1i—Ge1—O1110.95 (11)H3A—C3—H3Bi109.50
S1i—Ge1—O2108.95 (9)H3B—C3—H3Bi109.42
Ge1—S1—C197.60 (10)O2—C4—H4A108.77
Ge1—O1—C3114.6 (5)O2—C4—H4B109.85
Ge1—O2—C4114.0 (4)O2—C4—H4Bi109.85
S1—C1—C2115.4 (2)H4A—C4—H4B109.48
S1—C1—C1i124.4 (2)H4A—C4—H4Bi109.48
C1i—C1—C2120.2 (2)H4B—C4—H4Bi109.39
N1—C2—C1177.9 (3)
O1—Ge1—S1—C1123.77 (18)Ge1—S1—C1—C2172.7 (2)
O2—Ge1—S1—C1102.70 (15)Ge1—S1—C1—C1i7.5 (3)
S1i—Ge1—S1—C19.20 (11)S1—C1—C1i—C2i179.7 (2)
S1—Ge1—O1—C351.98 (6)C2—C1—C1i—S1i179.7 (2)
O2—Ge1—O1—C3180.00C2—C1—C1i—C2i0.0 (4)
S1—Ge1—O2—C451.07 (4)S1—C1—C1i—S1i0.0 (4)
Symmetry codes: (i) x, y, z; (ii) x1/2, y+1/2, z+1/2; (iii) x1/2, y+1/2, z1/2; (iv) x+1/2, y+1/2, z+1/2; (v) x+1/2, y+1/2, z+1/2; (vi) x+1, y, z; (vii) x+1, y+1, z; (viii) x+1, y+1, z; (ix) x, y, z; (x) x, y, z.

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