Di-tert-butyl­bis(N-isopropyl-N-methyl­dithio­carbamato-κ²S,S′)tin(IV)

The dithio­carbamate anions in the title compound, [Sn(C₄H₉)₂(C₅H₁₀NS₂)₂], chelate to the Sn^IV atom, which is six-coordinated in a skew-trapezoidal-bipyramidal geometry. The mol­ecule lies across a twofold rotation axis. The crystal studied was a non-merohedral twin, the ratio of the twin components being 0.82 (1):0.18 (1).

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.012 Å
• R factor = 0.062
• wR factor = 0.186
• Data-to-parameter ratio = 23.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Sn1    --  S2      ..      12.68 su

Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds (x 1000) Ang ..         12
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          9

Alert level G
PLAT128_ALERT_4_G Non-standard setting of Space-group P2/c    ....      P2/n
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT931_ALERT_5_G Check Twin Law ( 1 0  1)[       ] Estimated BASF       0.18

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level G
PUBL013_ALERT_1_G The _publ_section_comment (discussion of study) is
            missing. This is required for a full paper submission (but is
            optional for an electronic paper).

   0 ALERT level A = Data missing that is essential or data in wrong format
   1 ALERT level G = General alerts. Data that may be required is missing

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Related literature

For the crystal structure of di(tert-butyl)bis(N,N-dimethyldithiocarbamato)tin(IV), see: Kim et al. (1987). For a discussion of the geometry of tin in diorganotin bischelates, see: Ng et al. (1987). For the treatment of non-merohedral twinning, see: Spek (2009).

S1. Experimental

Di-t-butyltin dichloride (10 mmol), isopropylmethylamine (10 mmol) and carbon disulfide (10 mmol) were reacted in ethanol (50 ml) at 277 K to produce a white solid. The mixture was stirred for 1 h. The solid was collected and recrystallized from ethanol.

S2. Refinement

H atoms were placed in calculated positions (C–H = 0.93–0.98 Å) and were included in the refinement in the riding model approximation, with U_iso(H) set to 1.2-1.5U_eq(C). The structure is a non-merohedral twin. The diffraction data were separated into two components by using PLATON (Spek, 2009). The final difference Fourier map had a peak near S2 and a hole near Sn1. The twin matrix is (0.293 0 0.707, 0 -1 0, 1.293 0 -0.293).

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures

Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of [Sn(C6H5)2(C5H11NS2)2] at 50% probability level. H atoms are drawn as spheres of arbitrary radii. Unlabelled atoms are related to labelled atoms by the symmetry operation (3/2 - x, y, 3/2 - z).

Di-tert-butylbis(N-isopropyl-N-methyldithiocarbamato- κ²S,S')tin(IV)

Crystal data

[Sn(C4H9)2(C5H10NS2)2]	F(000) = 548
Mr = 529.43	Dx = 1.420 Mg m^−3
Monoclinic, P2/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yac	Cell parameters from 4020 reflections
a = 11.2934 (11) Å	θ = 2.6–28.1°
b = 7.0175 (7) Å	µ = 1.37 mm^−1
c = 15.6894 (15) Å	T = 293 K
β = 95.016 (1)°	Block, colourless
V = 1238.6 (2) Å^3	0.40 × 0.20 × 0.10 mm
Z = 2

Data collection

Bruker SMART APEX diffractometer	2838 independent reflections
Radiation source: fine-focus sealed tube	2199 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.610, Tmax = 0.875	k = −8→9
7346 measured reflections	l = −11→20

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.186	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0968P)^2 + 1.7978P] where P = (Fo^2 + 2Fc^2)/3
2838 reflections	(Δ/σ)max = 0.001
121 parameters	Δρmax = 1.76 e Å^−3
0 restraints	Δρmin = −1.58 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Sn1	0.7500	0.42189 (9)	0.7500	0.0369 (2)
S1	0.77107 (19)	0.1454 (3)	0.64749 (11)	0.0514 (5)
S2	0.82366 (17)	0.5223 (3)	0.57705 (11)	0.0469 (4)
N1	0.8073 (5)	0.2052 (8)	0.4857 (3)	0.0402 (12)
C1	0.5675 (6)	0.5241 (11)	0.7062 (4)	0.0426 (15)
C2	0.4811 (7)	0.3967 (12)	0.7504 (5)	0.059 (2)
H2A	0.4021	0.4474	0.7409	0.089*
H2B	0.5043	0.3925	0.8107	0.089*
H2C	0.4828	0.2702	0.7271	0.089*
C3	0.5406 (8)	0.5079 (17)	0.6112 (5)	0.070 (2)
H3A	0.4581	0.5351	0.5963	0.105*
H3B	0.5580	0.3809	0.5932	0.105*
H3C	0.5886	0.5972	0.5831	0.105*
C4	0.5556 (7)	0.7310 (12)	0.7355 (6)	0.060 (2)
H4A	0.4789	0.7793	0.7148	0.090*
H4B	0.6164	0.8071	0.7131	0.090*
H4C	0.5642	0.7362	0.7968	0.090*
C5	0.8030 (5)	0.2889 (9)	0.5620 (4)	0.0373 (13)
C6	0.8255 (8)	0.3238 (13)	0.4121 (5)	0.059 (2)
H6A	0.7772	0.4361	0.4134	0.089*
H6B	0.8038	0.2539	0.3605	0.089*
H6C	0.9077	0.3598	0.4138	0.089*
C7	0.7887 (7)	0.0018 (11)	0.4715 (5)	0.0501 (17)
H7A	0.8045	−0.0620	0.5269	0.060*
C8	0.6609 (11)	−0.0364 (16)	0.4406 (10)	0.102 (4)
H8A	0.6102	0.0090	0.4822	0.153*
H8B	0.6494	−0.1710	0.4325	0.153*
H8C	0.6418	0.0283	0.3872	0.153*
C9	0.8748 (12)	−0.0792 (14)	0.4117 (7)	0.097 (4)
H9A	0.9505	−0.0174	0.4222	0.145*
H9B	0.8442	−0.0579	0.3534	0.145*
H9C	0.8841	−0.2136	0.4216	0.145*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0481 (4)	0.0382 (4)	0.0266 (3)	0.000	0.0163 (2)	0.000
S1	0.0883 (13)	0.0388 (9)	0.0311 (8)	−0.0034 (9)	0.0284 (8)	0.0010 (7)
S2	0.0678 (11)	0.0352 (9)	0.0400 (9)	−0.0041 (8)	0.0169 (8)	0.0007 (7)
N1	0.053 (3)	0.040 (3)	0.029 (3)	0.000 (2)	0.017 (2)	−0.001 (2)
C1	0.041 (3)	0.051 (4)	0.038 (3)	−0.004 (3)	0.010 (3)	0.004 (3)
C2	0.053 (4)	0.076 (6)	0.051 (4)	−0.014 (4)	0.015 (3)	0.001 (4)
C3	0.059 (5)	0.110 (8)	0.041 (4)	0.007 (5)	0.003 (4)	0.000 (5)
C4	0.064 (5)	0.052 (5)	0.064 (5)	0.009 (4)	0.005 (4)	0.004 (4)
C5	0.046 (3)	0.038 (3)	0.030 (3)	0.004 (3)	0.015 (2)	0.005 (3)
C6	0.087 (5)	0.060 (5)	0.033 (3)	−0.007 (4)	0.020 (4)	0.006 (3)
C7	0.080 (5)	0.037 (4)	0.035 (3)	−0.001 (4)	0.014 (3)	−0.003 (3)
C8	0.095 (8)	0.071 (7)	0.134 (12)	−0.026 (6)	−0.018 (8)	−0.007 (7)
C9	0.159 (12)	0.064 (7)	0.075 (7)	0.013 (6)	0.062 (7)	−0.014 (5)

Geometric parameters (Å, º)

Sn1—C1^i	2.233 (7)	C3—H3B	0.96
Sn1—C1	2.233 (7)	C3—H3C	0.96
Sn1—S1	2.5444 (18)	C4—H4A	0.96
Sn1—S1^i	2.5444 (18)	C4—H4B	0.96
Sn1—S2^i	2.9911 (17)	C4—H4C	0.96
Sn1—S2	2.9911 (17)	C6—H6A	0.96
S1—C5	1.739 (6)	C6—H6B	0.96
S2—C5	1.669 (7)	C6—H6C	0.96
N1—C5	1.338 (8)	C7—C8	1.506 (13)
N1—C6	1.453 (9)	C7—C9	1.520 (12)
N1—C7	1.457 (10)	C7—H7A	0.98
C1—C3	1.500 (10)	C8—H8A	0.96
C1—C2	1.533 (10)	C8—H8B	0.96
C1—C4	1.532 (11)	C8—H8C	0.96
C2—H2A	0.96	C9—H9A	0.96
C2—H2B	0.96	C9—H9B	0.96
C2—H2C	0.96	C9—H9C	0.96
C3—H3A	0.96
C1^i—Sn1—C1	142.5 (4)	H3A—C3—H3C	109.5
C1^i—Sn1—S1	107.74 (18)	H3B—C3—H3C	109.5
C1—Sn1—S1	100.7 (2)	C1—C4—H4A	109.5
C1^i—Sn1—S1^i	100.7 (2)	C1—C4—H4B	109.5
C1—Sn1—S1^i	107.74 (19)	H4A—C4—H4B	109.5
S1—Sn1—S1^i	80.64 (8)	C1—C4—H4C	109.5
S1—Sn1—S2	63.73 (6)	H4A—C4—H4C	109.5
S1—Sn1—S2^i	143.31 (6)	H4B—C4—H4C	109.5
C1—Sn1—S2	88.14 (17)	N1—C5—S2	122.8 (5)
C1^i—Sn1—S2^i	88.14 (17)	N1—C5—S1	117.5 (5)
S1^i—Sn1—S2	143.31 (6)	S2—C5—S1	119.7 (4)
S2^i—Sn1—S2	152.75 (6)	N1—C6—H6A	109.5
C1—Sn1—S2^i	83.17 (17)	N1—C6—H6B	109.5
C1^i—Sn1—S2	83.17 (17)	H6A—C6—H6B	109.5
S1^i—Sn1—S2^i	63.73 (6)	N1—C6—H6C	109.5
C5—S1—Sn1	94.8 (2)	H6A—C6—H6C	109.5
C5—N1—C6	118.6 (6)	H6B—C6—H6C	109.5
C5—N1—C7	123.4 (5)	N1—C7—C8	110.2 (7)
C6—N1—C7	117.9 (6)	N1—C7—C9	111.7 (7)
C3—C1—C2	108.9 (7)	C8—C7—C9	112.4 (9)
C3—C1—C4	110.8 (7)	N1—C7—H7A	107.4
C2—C1—C4	110.0 (6)	C8—C7—H7A	107.4
C3—C1—Sn1	112.5 (5)	C9—C7—H7A	107.4
C2—C1—Sn1	106.3 (5)	C7—C8—H8A	109.5
C4—C1—Sn1	108.3 (5)	C7—C8—H8B	109.5
C1—C2—H2A	109.5	H8A—C8—H8B	109.5
C1—C2—H2B	109.5	C7—C8—H8C	109.5
H2A—C2—H2B	109.5	H8A—C8—H8C	109.5
C1—C2—H2C	109.5	H8B—C8—H8C	109.5
H2A—C2—H2C	109.5	C7—C9—H9A	109.5
H2B—C2—H2C	109.5	C7—C9—H9B	109.5
C1—C3—H3A	109.5	H9A—C9—H9B	109.5
C1—C3—H3B	109.5	C7—C9—H9C	109.5
H3A—C3—H3B	109.5	H9A—C9—H9C	109.5
C1—C3—H3C	109.5	H9B—C9—H9C	109.5
C1^i—Sn1—S1—C5	−76.5 (3)	S1^i—Sn1—C1—C4	117.8 (5)
C1—Sn1—S1—C5	78.8 (3)	C6—N1—C5—S2	−2.8 (9)
S1^i—Sn1—S1—C5	−174.8 (2)	C7—N1—C5—S2	−179.6 (5)
C1^i—Sn1—C1—C3	103.1 (6)	C6—N1—C5—S1	175.8 (5)
S1—Sn1—C1—C3	−35.9 (6)	C7—N1—C5—S1	−1.0 (8)
S1^i—Sn1—C1—C3	−119.4 (6)	Sn1—S1—C5—N1	−171.6 (5)
C1^i—Sn1—C1—C2	−137.8 (5)	Sn1—S1—C5—S2	7.0 (4)
S1—Sn1—C1—C2	83.1 (5)	C5—N1—C7—C8	95.0 (9)
S1^i—Sn1—C1—C2	−0.3 (5)	C6—N1—C7—C8	−81.9 (9)
C1^i—Sn1—C1—C4	−19.7 (4)	C5—N1—C7—C9	−139.4 (8)
S1—Sn1—C1—C4	−158.7 (5)	C6—N1—C7—C9	43.8 (10)

Symmetry code: (i) −x+3/2, y, −z+3/2.