2,2-Di­methoxy-1,3,2-di­thia­germole-4,5-dicarbo­nitrile

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.

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

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Computing details

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

Crystal data

[Ge(CH3O)2(C4N2S2)]	F(000) = 536
Mr = 272.86	Dx = 1.519 Mg m^−3
Orthorhombic, Pnnm	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2 2n	Cell parameters from 3800 reflections
a = 12.2960 (8) Å	θ = 5.3–56.1°
b = 9.7463 (7) Å	µ = 2.89 mm^−1
c = 9.9583 (7) Å	T = 293 K
V = 1193.41 (14) Å^3	Block, colourless
Z = 4	0.40 × 0.36 × 0.28 mm

Data collection

Siemens SMART CCD area-detector diffractometer	1469 independent reflections
Radiation source: fine-focus sealed tube	1230 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 8.33 pixels mm^-1	θmax = 28.3°, θmin = 2.6°
ω scans	h = −16→11
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −10→12
Tmin = 0.350, Tmax = 0.445	l = −13→13
6631 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.101	H-atom parameters not refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.053P)^2 + 0.6463P] where P = (Fo^2 + 2Fc^2)/3
1469 reflections	(Δ/σ)max < 0.001
67 parameters	Δρmax = 0.78 e Å^−3
0 restraints	Δρmin = −0.51 e Å^−3

Special details

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 F^{2 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 F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ge1	0.21928 (3)	0.32621 (4)	0.00000	0.0555 (2)
S1	0.34029 (7)	0.28757 (11)	0.16743 (7)	0.0702 (3)
O1	0.1713 (5)	0.5164 (5)	0.00000	0.1117 (19)
O2	0.1122 (4)	0.1806 (4)	0.00000	0.1033 (17)
N1	0.6082 (3)	0.1297 (4)	0.2018 (3)	0.0848 (10)
C1	0.4460 (2)	0.2246 (3)	0.0685 (3)	0.0557 (8)
C2	0.5368 (2)	0.1712 (3)	0.1405 (3)	0.0632 (9)
C3	0.2578 (8)	0.6156 (7)	0.00000	0.114 (3)
C4	0.1590 (7)	0.0422 (7)	0.00000	0.139 (4)
H3A	0.22640	0.70570	0.00000	0.1710*
H3B	0.30200	0.60420	0.07870	0.1710*	0.500
H4A	0.10090	−0.02350	0.00000	0.2090*
H4B	0.20300	0.02950	−0.07870	0.2090*	0.500

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ge1	0.0519 (3)	0.0617 (3)	0.0530 (3)	−0.0043 (2)	0.0000	0.0000
S1	0.0631 (4)	0.1076 (6)	0.0398 (3)	0.0034 (4)	0.0031 (3)	−0.0026 (3)
O1	0.136 (4)	0.093 (3)	0.106 (3)	0.001 (3)	0.0000	0.0000
O2	0.094 (3)	0.109 (3)	0.107 (3)	−0.018 (2)	0.0000	0.0000
N1	0.0646 (16)	0.116 (2)	0.0739 (18)	−0.0046 (16)	−0.0153 (14)	0.0137 (17)
C1	0.0480 (13)	0.0760 (15)	0.0432 (12)	−0.0080 (12)	−0.0005 (10)	0.0004 (11)
C2	0.0546 (14)	0.0857 (19)	0.0493 (13)	−0.0146 (13)	−0.0035 (12)	0.0030 (12)
C3	0.136 (6)	0.078 (4)	0.129 (6)	−0.029 (4)	0.0000	0.0000
C4	0.096 (5)	0.077 (4)	0.245 (11)	−0.027 (4)	0.0000	0.0000

Geometric parameters (Å, º)

Ge1—S1	2.2662 (8)	C1—C2	1.425 (4)
Ge1—O1	1.945 (5)	C1—C1^i	1.364 (4)
Ge1—O2	1.936 (4)	C3—H3A	0.9593
Ge1—S1^i	2.2662 (8)	C3—H3B	0.9602
S1—C1	1.743 (3)	C3—H3B^i	0.9602
O1—C3	1.437 (10)	C4—H4A	0.9594
O2—C4	1.467 (8)	C4—H4B	0.9603
N1—C2	1.143 (4)	C4—H4B^i	0.9603
Ge1···N1^ii	3.297 (3)	C2···C3^viii	3.557 (8)
Ge1···N1^iii	3.297 (3)	C3···C2^viii	3.557 (8)
S1···N1^ii	3.239 (4)	C3···C2^vii	3.557 (8)
S1···H4B^i	3.1554	C2···H3B^vii	3.0165
N1···Ge1^iv	3.297 (3)	H3B···C2^vii	3.0165
N1···S1^iv	3.239 (4)	H4A···H4A^ix	2.5233
N1···Ge1^v	3.297 (3)	H4A···H4A^x	2.5233
C2···C2^vi	3.458 (4)	H4B···S1^i	3.1554
C2···C3^vii	3.557 (8)
S1—Ge1—O1	110.95 (11)	O1—C3—H3A	108.54
S1—Ge1—O2	108.95 (9)	O1—C3—H3B	109.94
S1—Ge1—S1^i	94.74 (3)	O1—C3—H3B^i	109.94
O1—Ge1—O2	119.5 (2)	H3A—C3—H3B	109.50
S1^i—Ge1—O1	110.95 (11)	H3A—C3—H3B^i	109.50
S1^i—Ge1—O2	108.95 (9)	H3B—C3—H3B^i	109.42
Ge1—S1—C1	97.60 (10)	O2—C4—H4A	108.77
Ge1—O1—C3	114.6 (5)	O2—C4—H4B	109.85
Ge1—O2—C4	114.0 (4)	O2—C4—H4B^i	109.85
S1—C1—C2	115.4 (2)	H4A—C4—H4B	109.48
S1—C1—C1^i	124.4 (2)	H4A—C4—H4B^i	109.48
C1^i—C1—C2	120.2 (2)	H4B—C4—H4B^i	109.39
N1—C2—C1	177.9 (3)
O1—Ge1—S1—C1	−123.77 (18)	Ge1—S1—C1—C2	−172.7 (2)
O2—Ge1—S1—C1	102.70 (15)	Ge1—S1—C1—C1^i	7.5 (3)
S1^i—Ge1—S1—C1	−9.20 (11)	S1—C1—C1^i—C2^i	179.7 (2)
S1—Ge1—O1—C3	51.98 (6)	C2—C1—C1^i—S1^i	−179.7 (2)
O2—Ge1—O1—C3	180.00	C2—C1—C1^i—C2^i	0.0 (4)
S1—Ge1—O2—C4	−51.07 (4)	S1—C1—C1^i—S1^i	0.0 (4)
O1—Ge1—O2—C4	180.00

Symmetry codes: (i) x, y, −z; (ii) x−1/2, −y+1/2, −z+1/2; (iii) x−1/2, −y+1/2, z−1/2; (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.