2-(2,2-Di­methyl-1,3,2-di­thia­germetan-4-yl­idene)­malono­nitrile

Akkurt, M.; Öztürk, S.; Kök, T.R.; Heinemann, F.W.

doi:10.1107/S160053680400488X

2-(2,2-Dimethyl-1,3,2-dithiagermetan-4-ylidene)malononitrile

M. Akkurt, S. Öztürk, T. R. Kök and F. W. Heinemann

The title compound, [Ge(CH₃)₂(C₄N₂S₂)], crystallizes in the space group Pnma, with two half-molecules in the asymmetric unit. The C atoms of the two methyl groups lie on the same mirror plane as the Ge atom and the –C=C– group. The S atoms and nitrile groups are each symmetry-related across the mirror plane. The structure is stabilized by intermolecular C—H

N hydrogen interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680400488X/na6299sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680400488X/na6299Isup2.hkl Contains datablock I

CCDC reference: 238628

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.005 Å
R factor = 0.046
wR factor = 0.073
Data-to-parameter ratio = 19.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.20 Ratio
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C4A    -   C5A    ...       1.42 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C4A    -   C5A_a  ...       1.42 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C4B    -   C5B    ...       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C4B    -   C5B_b  ...       1.43 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 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
   4 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: 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).

2[2,2-Dimethyl[1,3,2]dithiagermetan-4-ylidene]malononitrile top

Crystal data top

[Ge(CH₃)₂(C₄N₂S₂)]	F(000) = 960
M_r = 242.88	D_x = 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

Data collection top

Nonius KappaCCD area-detector diffractometer	2452 independent reflections
Radiation source: fine-focus sealed tube	1413 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
Detector resolution: 9 pixels mm^-1	θ_max = 28.5°, θ_min = 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
T_min = 0.560, T_max = 0.784	l = −9→9
25208 measured reflections

Refinement top

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(F_o²) + (0.0252P)² + 0.922P] where P = (F_o² + 2F_c²)/3
2452 reflections	(Δ/σ)_max < 0.001
123 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.74 e Å⁻³

Special details top

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 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} ^F2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of} ^F2 > 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} ^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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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···N1A^iv	2.965 (4)	C1B···N1A^v	3.297 (5)
Ge1B···N1A^v	2.965 (4)	C1B···S1Bⁱ	3.488 (5)
S1A···C1A	3.544 (6)	C1B···N1A^iv	3.297 (5)
S1A···N1Bⁱⁱⁱ	3.127 (3)	C1B···S1B	3.488 (5)
S1A···S1Aⁱ	2.9041 (13)	C1B···C2B	3.393 (7)
S1A···C5B^vi	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···N1A^iv	3.131 (3)	C2A···S1A	3.444 (5)
S1B···C1B	3.488 (5)	C2A···C1A	3.397 (8)
S1B···C2B	3.460 (7)	C2B···N1A^v	3.194 (5)
N1A···C2B^vii	3.194 (5)	C2B···S1B	3.460 (7)
N1A···S1B^vii	3.131 (3)	C2B···C1B	3.393 (7)
N1A···C1B^vii	3.297 (5)	C2B···S1Bⁱ	3.460 (7)
N1A···Ge1B^vii	2.965 (4)	C2B···N1A^iv	3.194 (5)
N1A···C1B^v	3.297 (5)	C4A···C4B^x	3.541 (6)
N1A···C2B^v	3.194 (5)	C4A···C4B^xi	3.541 (6)
N1A···Ge1B^v	2.965 (4)	C4B···C4A^xii	3.541 (6)
N1B···C2A^viii	3.308 (5)	C4B···C4A^xiii	3.541 (6)
N1B···Ge1A^viii	2.961 (4)	C5B···S1A^xiv	3.683 (3)
N1B···C1A^ix	3.182 (5)	C5A···H4^xv	3.0354
N1B···C2A^ix	3.308 (5)	C5A···H4^vi	3.0354
N1B···S1A^ix	3.127 (3)	C5B···H1^xvi	3.0221
N1B···C1A^viii	3.182 (5)	C5B···H1^xiv	3.0221
N1B···Ge1A^ix	2.961 (4)	H1···C5B^xv	3.0221
N1A···H5^v	2.7466	H1···C5B^vi	3.0221
N1A···H11^vii	2.6165	H2···N1Bⁱⁱⁱ	2.6054
N1B···H8^viii	2.7642	H4···C5A^xiv	3.0354
N1B···H2^ix	2.6054	H4···C5A^xvi	3.0354
C1A···N1Bⁱⁱ	3.182 (5)	H5···N1A^v	2.7466
C1A···S1A	3.544 (6)	H8···N1Bⁱⁱ	2.7642
C1A···C2A	3.397 (8)	H11···N1A^iv	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.

Hydrogen-bond geometry (Å, º) top

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···N1A^iv	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.

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2-(2,2-Di­methyl-1,3,2-di­thia­germetan-4-yl­idene)­malono­nitrile

Supporting information

Key indicators

checkCIF/PLATON results

2-(2,2-Dimethyl-1,3,2-dithiagermetan-4-ylidene)malononitrile