Bis(3,5-dimethyl­pyridine-κN)bis­(tri-tert-butoxy­silanethiol­ato-κS)chromium(II) toluene solvate

Ciborska, A.; Baranowska, K.; Wojnowski, W.

doi:10.1107/S1600536809021680

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m763

doi:10.1107/S1600536809021680

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Bis(3,5-dimethylpyridine-κN)bis(tri-tert-butoxysilanethiolato-κS)chromium(II) toluene solvate

Anna Ciborska,^a Katarzyna Baranowska ^a ^* and Wiesław Wojnowski ^a

^aDepartment of Chemistry, Technical University of Gdańsk, 11/12 G. Narutowicz St., 80233–PL Gdańsk, Poland
^*Correspondence e-mail: kasiab29@wp.pl

(Received 27 May 2009; accepted 8 June 2009; online 13 June 2009)

In the title chromium silanethiolate, [Cr(C₁₂H₂₇O₃SSi)₂(C₇H₉N)₂]·C₇H₈, the Cr^II atom is coordinated by two S and two N atoms in a distorted square-planar geometrical arrangement. The mononuclear molecule lies on a twofold axis that passes through the pyridine N atoms. The toluene solvent molecule is equally disordered about a twofold axis.

Related literature

For the synthetic procedures, see: Perrin & Armarego (1988 ); Piękoś & Wojnowski (1962 ); Wojnowska & Wojnowski (1974 ). For the use of such complexes in model studies of proteins, see: Becker et al. (2002 ); Dołęga et al. (2008 ). For another Cr–thiolate, see: Dorfman et al. (1985 ). For related strutures, see: Ciborska et al. (2007 , 2008 ).

Experimental

Crystal data

[Cr(C₁₂H₂₇O₃SSi)₂(C₇H₉N)₂]·C₇H₈
M_r = 917.41
Monoclinic, C 2/c
a = 19.6147 (4) Å
b = 17.1521 (17) Å
c = 17.2221 (9) Å
β = 112.047 (5)°
V = 5370.4 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 120 K
0.32 × 0.30 × 0.19 mm

Data collection

Oxford Diffraction KM-4-CCD diffractometer
Absorption correction: none
18436 measured reflections
5260 independent reflections
4788 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.148
S = 1.11
5260 reflections
296 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 1.14 e Å⁻³
Δρ_min = −0.78 e Å⁻³

Table 1
Selected bond lengths (Å)

Cr1—N1	2.136 (3)
Cr1—N2	2.153 (3)
Cr1—S1	2.4426 (6)
S1—Si1	2.0694 (8)
Si1—O3	1.6342 (17)
Si1—O2	1.6370 (17)
Si1—O1	1.6480 (17)

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809021680/ng2589sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809021680/ng2589Isup2.hkl

checkCIF report

Comment top

The large development of transition-metal silanethiolate chemistry results from its potential to form new types of complexes with interesting chemical properties. These complexes may be used in model studies on structural and catalytic metal centers in proteins (Becker et al. 2002; Dołęga et al. 2008). Here we present the synthesis and molecular structure of the chromium(II), tri-tert-butoxysilanethiolate complex [Cr(C₁₂H₂₇O₃SSi)₂(C₇H₉N)₂] C₇H₈.The crystal structure of the title compound (I) is one of the few structurally defined four-coordinate Cr^II thiolate complexes (Dorfman et al. 1985; Ciborska et al. 2008). This complex was obtained as light-blue crystals in the reaction of anhydrous Cr^II chloride with sodium tri-tert-butoxysilanethiolate and 3,5-dimethylpyridine. The Cr^II ion is coordinated by two S atoms from the tri-tert-butoxysilanethiolate ligands and two N atoms from the 3,5-dimethylpyridine molecules. The trans angles of the square base are then described by S—Cr—S and N—Cr—N, which are very close to 180°. The Cr—S bond lengths in (I) are very similar to the corresponding values of ca 2.4 Å observed in the other silanethiolates (Ciborska et al.2007). The Cr—N bond lengths are like these found in the [Cr(C₁₂H₂₇O₃SSi)₂(C₆H₁₅N)₂]. Selected data of important bond lengths and angles are compared in Table 1.

Related literature top

For the synthetic procedures, see: Perrin & Armarego (1988); Piękoś & Wojnowski (1962); Wojnowska & Wojnowski (1974). For the use of such complexes in model studies of proteins, see: Becker et al. (2002); Dołęga et al. (2008). For another Cr–thiolate, see: Dorfman et al. (1985). For related strutures, see: Ciborska et al., (2007, 2008).

Experimental top

The synthesis was carried out under an atmosphere of nitrogen, using standard Schlenk techniques. Solvents and the amine were purified and dried by standard methods (Perrin & Armarego, 1988). The substrate (^tBuO)₃SiSNa was prepared according to literature methods (Piękoś & Wojnowski, 1962; Wojnowska & Wojnowski, 1974). The title compound was synthesized by addition of the CrCl₂ solution (0.143 g, 1.16 mmol) in tetrahydrofuran (10 ml) to (^tBuO)₃SiSNa solution (0.833 g, 2.7 mmol) in toluene (10 ml) and stirring for 1 h.

3,5-Dimethylpyridine (0,267 g, 0.28 ml, 2.5 mmol) was subsequently added to the solution and stirred for next 12 h. After that the mixture was concentrated and cooled (250 K) to afford light-blue crystals.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. A view of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms have been omitted.

Bis(3,5-dimethylpyridine-κN)bis(tri-tert-butoxysilanethiolato- κS)chromium(II) toluene solvate top

Crystal data top

[Cr(C₁₂H₂₇O₃SSi)₂(C₇H₉N)₂]·C₇H₈	F(000) = 1984
M_r = 917.41	D_x = 1.135 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 20255 reflections
a = 19.6147 (4) Å	θ = 2.4–32.5°
b = 17.1521 (17) Å	µ = 0.38 mm⁻¹
c = 17.2221 (9) Å	T = 120 K
β = 112.047 (5)°	Prism, blue
V = 5370.4 (6) Å³	0.32 × 0.3 × 0.19 mm
Z = 4

Data collection top

Oxford Diffraction KM-4-CCD diffractometer	4788 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 8.1883 pixels mm^-1	θ_max = 26°, θ_min = 2.7°
ω scans	h = −24→24
18436 measured reflections	k = −15→21
5260 independent reflections	l = −21→21

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0822P)² + 9.051P] where P = (F_o² + 2F_c²)/3
5260 reflections	(Δ/σ)_max < 0.001
296 parameters	Δρ_max = 1.14 e Å⁻³
1 restraint	Δρ_min = −0.78 e Å⁻³

Crystal data top

[Cr(C₁₂H₂₇O₃SSi)₂(C₇H₉N)₂]·C₇H₈	V = 5370.4 (6) Å³
M_r = 917.41	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 19.6147 (4) Å	µ = 0.38 mm⁻¹
b = 17.1521 (17) Å	T = 120 K
c = 17.2221 (9) Å	0.32 × 0.3 × 0.19 mm
β = 112.047 (5)°

Data collection top

Oxford Diffraction KM-4-CCD diffractometer	4788 reflections with I > 2σ(I)
18436 measured reflections	R_int = 0.031
5260 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	1 restraint
wR(F²) = 0.148	H-atom parameters constrained
S = 1.11	Δρ_max = 1.14 e Å⁻³
5260 reflections	Δρ_min = −0.78 e Å⁻³
296 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) 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	Occ. (<1)
Cr1	0	0.01937 (3)	0.25	0.01892 (16)
S1	0.10684 (3)	0.02265 (3)	0.38160 (3)	0.01235 (16)
Si1	0.17518 (3)	0.00414 (4)	0.31651 (4)	0.02545 (17)
O1	0.12513 (9)	0.02386 (9)	0.21779 (10)	0.0220 (4)
O2	0.25116 (9)	0.05527 (10)	0.35177 (10)	0.0244 (4)
O3	0.20219 (9)	−0.08576 (9)	0.31481 (10)	0.0244 (4)
N1	0	0.14391 (15)	0.25	0.0205 (6)
N2	0	−0.10614 (15)	0.25	0.0200 (5)
C1	0.14053 (14)	0.01078 (14)	0.14221 (14)	0.0240 (5)
C2	0.11660 (17)	−0.07146 (16)	0.11088 (17)	0.0351 (6)
H2A	0.1434	−0.1091	0.1545	0.053*
H2B	0.1273	−0.0813	0.0605	0.053*
H2C	0.0637	−0.0771	0.0974	0.053*
C3	0.09435 (17)	0.07101 (17)	0.07930 (16)	0.0364 (6)
H3A	0.0422	0.063	0.0692	0.055*
H3B	0.102	0.0652	0.0265	0.055*
H3C	0.1091	0.1235	0.1018	0.055*
C4	0.22130 (16)	0.02209 (17)	0.15862 (17)	0.0346 (6)
H4A	0.2354	0.076	0.1763	0.052*
H4B	0.2301	0.0113	0.1073	0.052*
H4C	0.2507	−0.0137	0.2029	0.052*
C5	0.26593 (14)	0.13476 (14)	0.38092 (16)	0.0274 (5)
C6	0.20424 (15)	0.18905 (15)	0.32786 (19)	0.0364 (6)
H6A	0.1976	0.184	0.2688	0.055*
H6B	0.2171	0.243	0.346	0.055*
H6C	0.1584	0.1749	0.3347	0.055*
C7	0.33779 (15)	0.15658 (17)	0.37182 (18)	0.0356 (6)
H7A	0.3762	0.1193	0.403	0.053*
H7B	0.3525	0.2092	0.3941	0.053*
H7C	0.331	0.1553	0.3125	0.053*
C8	0.27486 (16)	0.13697 (17)	0.47279 (17)	0.0369 (6)
H8A	0.2282	0.1227	0.4776	0.055*
H8B	0.2889	0.1897	0.495	0.055*
H8C	0.3132	0.1	0.5048	0.055*
C9	0.25415 (14)	−0.13435 (15)	0.37758 (16)	0.0291 (5)
C10	0.32921 (17)	−0.1211 (2)	0.3753 (2)	0.0541 (9)
H10A	0.3283	−0.1342	0.3195	0.081*
H10B	0.3652	−0.1542	0.4173	0.081*
H10C	0.343	−0.0663	0.3875	0.081*
C11	0.25326 (19)	−0.11775 (19)	0.46367 (18)	0.0451 (8)
H11A	0.2685	−0.0637	0.4793	0.068*
H11B	0.2873	−0.1532	0.5047	0.068*
H11C	0.2034	−0.1256	0.4626	0.068*
C12	0.2294 (2)	−0.21788 (17)	0.3515 (2)	0.0490 (8)
H12A	0.1813	−0.2267	0.3552	0.073*
H12B	0.2654	−0.2543	0.3888	0.073*
H12C	0.2255	−0.2264	0.2937	0.073*
C13	0.00905 (12)	0.18436 (13)	0.31980 (14)	0.0220 (5)
H13	0.0157	0.1562	0.3696	0.026*
C14	0.00919 (13)	0.26521 (14)	0.32324 (15)	0.0234 (5)
C15	0.02036 (16)	0.30602 (16)	0.40425 (17)	0.0352 (6)
H15A	0.0273	0.2672	0.4484	0.053*
H15B	−0.0229	0.338	0.3975	0.053*
H15C	0.064	0.3394	0.4197	0.053*
C16	0	0.30546 (19)	0.25	0.0254 (7)
H16	0	0.3608	0.25	0.03*
C17	0.02288 (12)	−0.14715 (13)	0.32193 (14)	0.0217 (5)
H17	0.0402	−0.1192	0.3733	0.026*
C18	0.02260 (13)	−0.22816 (14)	0.32521 (15)	0.0250 (5)
C19	0	−0.26836 (19)	0.25	0.0270 (7)
H19	0	−0.3237	0.25	0.032*
C20	0.04651 (18)	−0.26906 (16)	0.40847 (17)	0.0371 (6)
H20A	0.0038	−0.2936	0.4149	0.056*
H20B	0.0683	−0.2311	0.4536	0.056*
H20C	0.083	−0.3091	0.4112	0.056*
C21	0.0088 (6)	0.5182 (7)	0.3429 (6)	0.0241 (15)	0.5
C22	−0.0610 (6)	0.5206 (13)	0.2802 (6)	0.028 (2)	0.5
H22	−0.1032	0.5226	0.2946	0.034*	0.5
C23	−0.0690 (8)	0.5202 (13)	0.1965 (6)	0.029 (2)	0.5
H23	−0.1167	0.5218	0.1537	0.035*	0.5
C24	−0.0072 (9)	0.5173 (8)	0.1755 (6)	0.048 (4)	0.5
H24	−0.0126	0.517	0.1183	0.057*	0.5
C25	0.0627 (8)	0.5149 (14)	0.2382 (7)	0.036 (3)	0.5
H25	0.1049	0.513	0.2239	0.044*	0.5
C26	0.0706 (7)	0.5154 (13)	0.3219 (7)	0.039 (3)	0.5
H26	0.1184	0.5137	0.3648	0.047*	0.5
C27	0.0179 (4)	0.5168 (3)	0.4338 (4)	0.0368 (13)	0.5
H27A	0.0156	0.5702	0.453	0.055*	0.5
H27B	0.0656	0.4937	0.4674	0.055*	0.5
H27C	−0.0216	0.4857	0.4401	0.055*	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cr1	0.0213 (3)	0.0152 (3)	0.0155 (3)	0	0.0016 (2)	0
S1	0.0139 (3)	0.0144 (3)	0.0075 (3)	−0.0006 (2)	0.0026 (2)	−0.00006 (19)
Si1	0.0257 (3)	0.0285 (3)	0.0204 (3)	0.0003 (2)	0.0066 (2)	0.0009 (2)
O1	0.0229 (9)	0.0295 (9)	0.0131 (8)	0.0027 (6)	0.0061 (7)	0.0011 (6)
O2	0.0225 (8)	0.0255 (9)	0.0236 (8)	−0.0022 (7)	0.0068 (7)	−0.0024 (7)
O3	0.0275 (9)	0.0237 (8)	0.0200 (8)	0.0046 (7)	0.0067 (7)	0.0016 (6)
N1	0.0193 (13)	0.0177 (12)	0.0214 (14)	0	0.0041 (11)	0
N2	0.0192 (13)	0.0183 (13)	0.0207 (13)	0	0.0055 (11)	0
C1	0.0275 (13)	0.0318 (13)	0.0137 (11)	0.0027 (10)	0.0088 (10)	0.0008 (9)
C2	0.0471 (16)	0.0386 (14)	0.0239 (13)	−0.0075 (12)	0.0181 (12)	−0.0066 (11)
C3	0.0457 (16)	0.0467 (16)	0.0183 (12)	0.0147 (13)	0.0136 (11)	0.0066 (11)
C4	0.0306 (14)	0.0506 (17)	0.0263 (13)	−0.0019 (12)	0.0150 (11)	0.0005 (11)
C5	0.0252 (12)	0.0269 (12)	0.0288 (13)	−0.0064 (10)	0.0087 (10)	−0.0043 (10)
C6	0.0303 (14)	0.0275 (13)	0.0488 (17)	−0.0019 (11)	0.0118 (13)	0.0023 (12)
C7	0.0284 (14)	0.0377 (15)	0.0408 (16)	−0.0096 (11)	0.0130 (12)	−0.0052 (12)
C8	0.0353 (15)	0.0412 (15)	0.0335 (15)	−0.0105 (12)	0.0121 (12)	−0.0136 (12)
C9	0.0285 (13)	0.0301 (13)	0.0300 (13)	0.0100 (10)	0.0125 (11)	0.0108 (10)
C10	0.0298 (16)	0.072 (2)	0.060 (2)	0.0130 (15)	0.0159 (15)	0.0320 (18)
C11	0.0519 (18)	0.0530 (18)	0.0287 (15)	0.0221 (15)	0.0133 (13)	0.0149 (13)
C12	0.059 (2)	0.0293 (15)	0.063 (2)	0.0131 (14)	0.0279 (17)	0.0060 (14)
C13	0.0190 (11)	0.0231 (11)	0.0215 (11)	−0.0005 (9)	0.0048 (9)	0.0004 (9)
C14	0.0196 (11)	0.0231 (11)	0.0267 (12)	−0.0001 (9)	0.0076 (9)	−0.0039 (9)
C15	0.0408 (15)	0.0310 (13)	0.0333 (14)	0.0023 (11)	0.0135 (12)	−0.0091 (11)
C16	0.0237 (17)	0.0175 (15)	0.0328 (19)	0	0.0082 (14)	0
C17	0.0206 (11)	0.0227 (11)	0.0199 (11)	−0.0007 (9)	0.0054 (9)	0.0005 (9)
C18	0.0240 (12)	0.0216 (11)	0.0275 (13)	0.0002 (9)	0.0073 (10)	0.0048 (9)
C19	0.0297 (18)	0.0162 (15)	0.0338 (19)	0	0.0105 (15)	0
C20	0.0503 (17)	0.0275 (13)	0.0287 (14)	−0.0016 (12)	0.0094 (12)	0.0078 (11)
C21	0.020 (4)	0.014 (3)	0.034 (4)	−0.001 (2)	0.006 (3)	−0.003 (3)
C22	0.031 (5)	0.018 (4)	0.034 (4)	0.001 (3)	0.011 (4)	−0.008 (4)
C23	0.025 (4)	0.022 (4)	0.032 (5)	−0.002 (3)	0.001 (3)	−0.006 (4)
C24	0.090 (10)	0.026 (5)	0.038 (6)	0.000 (5)	0.036 (6)	0.003 (4)
C25	0.039 (5)	0.027 (5)	0.050 (7)	0.003 (4)	0.026 (4)	0.012 (6)
C26	0.045 (6)	0.027 (6)	0.047 (6)	−0.001 (4)	0.018 (6)	0.003 (6)
C27	0.045 (3)	0.024 (3)	0.038 (3)	0.000 (2)	0.012 (3)	0.000 (2)

Geometric parameters (Å, º) top

Cr1—N1	2.136 (3)	C10—H10A	0.98
Cr1—N2	2.153 (3)	C10—H10B	0.98
Cr1—S1ⁱ	2.4426 (6)	C10—H10C	0.98
Cr1—S1	2.4426 (6)	C11—H11A	0.98
S1—Si1	2.0694 (8)	C11—H11B	0.98
Si1—O3	1.6342 (17)	C11—H11C	0.98
Si1—O2	1.6370 (17)	C12—H12A	0.98
Si1—O1	1.6480 (17)	C12—H12B	0.98
O1—C1	1.460 (3)	C12—H12C	0.98
O2—C5	1.444 (3)	C13—C14	1.388 (3)
O3—C9	1.441 (3)	C13—H13	0.95
N1—C13	1.341 (3)	C14—C16	1.389 (3)
N1—C13ⁱ	1.341 (3)	C14—C15	1.502 (3)
N2—C17ⁱ	1.347 (3)	C15—H15A	0.98
N2—C17	1.347 (3)	C15—H15B	0.98
C1—C4	1.514 (4)	C15—H15C	0.98
C1—C2	1.520 (4)	C16—C14ⁱ	1.389 (3)
C1—C3	1.525 (3)	C16—H16	0.95
C2—H2A	0.98	C17—C18	1.391 (3)
C2—H2B	0.98	C17—H17	0.95
C2—H2C	0.98	C18—C19	1.385 (3)
C3—H3A	0.98	C18—C20	1.504 (3)
C3—H3B	0.98	C19—C18ⁱ	1.385 (3)
C3—H3C	0.98	C19—H19	0.95
C4—H4A	0.98	C20—H20A	0.98
C4—H4B	0.98	C20—H20B	0.98
C4—H4C	0.98	C20—H20C	0.98
C5—C7	1.522 (4)	C21—C22	1.39
C5—C8	1.526 (4)	C21—C26	1.39
C5—C6	1.528 (4)	C21—C27	1.508 (9)
C6—H6A	0.98	C22—C23	1.39
C6—H6B	0.98	C22—H22	0.95
C6—H6C	0.98	C23—C24	1.39
C7—H7A	0.98	C23—H23	0.95
C7—H7B	0.98	C24—C25	1.39
C7—H7C	0.98	C24—H24	0.95
C8—H8A	0.98	C25—C26	1.39
C8—H8B	0.98	C25—H25	0.95
C8—H8C	0.98	C26—H26	0.95
C9—C10	1.505 (4)	C27—H27A	0.98
C9—C11	1.516 (4)	C27—H27B	0.98
C9—C12	1.525 (4)	C27—H27C	0.98

N1—Cr1—N2	180	O3—C9—C11	111.1 (2)
N1—Cr1—S1ⁱ	88.677 (16)	C10—C9—C11	111.6 (3)
N2—Cr1—S1ⁱ	91.323 (16)	O3—C9—C12	105.4 (2)
N1—Cr1—S1	88.677 (16)	C10—C9—C12	109.9 (3)
N2—Cr1—S1	91.323 (16)	C11—C9—C12	110.2 (2)
S1ⁱ—Cr1—S1	177.35 (3)	C9—C10—H10A	109.5
Si1—S1—Cr1	89.91 (3)	C9—C10—H10B	109.5
O3—Si1—O2	104.84 (9)	H10A—C10—H10B	109.5
O3—Si1—O1	104.28 (9)	C9—C10—H10C	109.5
O2—Si1—O1	112.30 (9)	H10A—C10—H10C	109.5
O3—Si1—S1	115.77 (7)	H10B—C10—H10C	109.5
O2—Si1—S1	113.67 (7)	C9—C11—H11A	109.5
O1—Si1—S1	105.74 (7)	C9—C11—H11B	109.5
C1—O1—Si1	130.23 (15)	H11A—C11—H11B	109.5
C5—O2—Si1	132.12 (15)	C9—C11—H11C	109.5
C9—O3—Si1	132.47 (16)	H11A—C11—H11C	109.5
C13—N1—C13ⁱ	117.7 (3)	H11B—C11—H11C	109.5
C13—N1—Cr1	121.16 (14)	C9—C12—H12A	109.5
C13ⁱ—N1—Cr1	121.16 (14)	C9—C12—H12B	109.5
C17ⁱ—N2—C17	117.0 (3)	H12A—C12—H12B	109.5
C17ⁱ—N2—Cr1	121.49 (14)	C9—C12—H12C	109.5
C17—N2—Cr1	121.49 (14)	H12A—C12—H12C	109.5
O1—C1—C4	111.5 (2)	H12B—C12—H12C	109.5
O1—C1—C2	108.63 (19)	N1—C13—C14	123.6 (2)
C4—C1—C2	110.3 (2)	N1—C13—H13	118.2
O1—C1—C3	105.24 (19)	C14—C13—H13	118.2
C4—C1—C3	110.3 (2)	C13—C14—C16	117.4 (2)
C2—C1—C3	110.8 (2)	C13—C14—C15	120.2 (2)
C1—C2—H2A	109.5	C16—C14—C15	122.4 (2)
C1—C2—H2B	109.5	C14—C15—H15A	109.5
H2A—C2—H2B	109.5	C14—C15—H15B	109.5
C1—C2—H2C	109.5	H15A—C15—H15B	109.5
H2A—C2—H2C	109.5	C14—C15—H15C	109.5
H2B—C2—H2C	109.5	H15A—C15—H15C	109.5
C1—C3—H3A	109.5	H15B—C15—H15C	109.5
C1—C3—H3B	109.5	C14ⁱ—C16—C14	120.4 (3)
H3A—C3—H3B	109.5	C14ⁱ—C16—H16	119.8
C1—C3—H3C	109.5	C14—C16—H16	119.8
H3A—C3—H3C	109.5	N2—C17—C18	123.7 (2)
H3B—C3—H3C	109.5	N2—C17—H17	118.2
C1—C4—H4A	109.5	C18—C17—H17	118.2
C1—C4—H4B	109.5	C19—C18—C17	117.6 (2)
H4A—C4—H4B	109.5	C19—C18—C20	122.3 (2)
C1—C4—H4C	109.5	C17—C18—C20	120.0 (2)
H4A—C4—H4C	109.5	C18—C19—C18ⁱ	120.3 (3)
H4B—C4—H4C	109.5	C18—C19—H19	119.9
O2—C5—C7	105.6 (2)	C18ⁱ—C19—H19	119.9
O2—C5—C8	108.3 (2)	C18—C20—H20A	109.5
C7—C5—C8	110.5 (2)	C18—C20—H20B	109.5
O2—C5—C6	110.9 (2)	H20A—C20—H20B	109.5
C7—C5—C6	110.2 (2)	C18—C20—H20C	109.5
C8—C5—C6	111.2 (2)	H20A—C20—H20C	109.5
C5—C6—H6A	109.5	H20B—C20—H20C	109.5
C5—C6—H6B	109.5	C22—C21—C26	120
H6A—C6—H6B	109.5	C22—C21—C27	120.3 (4)
C5—C6—H6C	109.5	C26—C21—C27	119.7 (4)
H6A—C6—H6C	109.5	C21—C22—C23	120
H6B—C6—H6C	109.5	C21—C22—H22	120
C5—C7—H7A	109.5	C23—C22—H22	120
C5—C7—H7B	109.5	C24—C23—C22	120
H7A—C7—H7B	109.5	C24—C23—H23	120
C5—C7—H7C	109.5	C22—C23—H23	120
H7A—C7—H7C	109.5	C23—C24—C25	120
H7B—C7—H7C	109.5	C23—C24—H24	120
C5—C8—H8A	109.5	C25—C24—H24	120
C5—C8—H8B	109.5	C26—C25—C24	120
H8A—C8—H8B	109.5	C26—C25—H25	120
C5—C8—H8C	109.5	C24—C25—H25	120
H8A—C8—H8C	109.5	C25—C26—C21	120
H8B—C8—H8C	109.5	C25—C26—H26	120
O3—C9—C10	108.4 (2)	C21—C26—H26	120

N1—Cr1—S1—Si1	−98.83 (2)	Si1—O2—C5—C8	83.6 (3)
N2—Cr1—S1—Si1	81.17 (2)	Si1—O2—C5—C6	−38.7 (3)
Cr1—S1—Si1—O3	−98.51 (7)	Si1—O3—C9—C10	−87.7 (3)
Cr1—S1—Si1—O2	140.02 (7)	Si1—O3—C9—C11	35.3 (3)
Cr1—S1—Si1—O1	16.37 (7)	Si1—O3—C9—C12	154.7 (2)
O3—Si1—O1—C1	−47.8 (2)	C13ⁱ—N1—C13—C14	0.29 (17)
O2—Si1—O1—C1	65.2 (2)	Cr1—N1—C13—C14	−179.71 (17)
S1—Si1—O1—C1	−170.29 (18)	N1—C13—C14—C16	−0.6 (3)
O3—Si1—O2—C5	−167.93 (19)	N1—C13—C14—C15	−179.5 (2)
O1—Si1—O2—C5	79.5 (2)	C13—C14—C16—C14ⁱ	0.26 (15)
S1—Si1—O2—C5	−40.5 (2)	C15—C14—C16—C14ⁱ	179.1 (3)
O2—Si1—O3—C9	52.9 (2)	C17ⁱ—N2—C17—C18	−1.29 (17)
O1—Si1—O3—C9	171.1 (2)	Cr1—N2—C17—C18	178.71 (17)
S1—Si1—O3—C9	−73.2 (2)	N2—C17—C18—C19	2.5 (3)
S1ⁱ—Cr1—N1—C13	135.55 (11)	N2—C17—C18—C20	−177.7 (2)
S1—Cr1—N1—C13	−44.45 (11)	C17—C18—C19—C18ⁱ	−1.16 (15)
S1ⁱ—Cr1—N1—C13ⁱ	−44.45 (11)	C20—C18—C19—C18ⁱ	179.0 (3)
S1—Cr1—N1—C13ⁱ	135.55 (11)	C26—C21—C22—C23	0
S1ⁱ—Cr1—N2—C17ⁱ	31.46 (11)	C27—C21—C22—C23	−178.6 (12)
S1—Cr1—N2—C17ⁱ	−148.54 (11)	C21—C22—C23—C24	0
S1ⁱ—Cr1—N2—C17	−148.54 (11)	C22—C23—C24—C25	0
S1—Cr1—N2—C17	31.46 (11)	C23—C24—C25—C26	0
Si1—O1—C1—C4	−35.4 (3)	C24—C25—C26—C21	0
Si1—O1—C1—C2	86.4 (3)	C22—C21—C26—C25	0
Si1—O1—C1—C3	−154.96 (19)	C27—C21—C26—C25	178.6 (12)
Si1—O2—C5—C7	−158.01 (18)

Symmetry code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Cr(C₁₂H₂₇O₃SSi)₂(C₇H₉N)₂]·C₇H₈
M_r	917.41
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	120
a, b, c (Å)	19.6147 (4), 17.1521 (17), 17.2221 (9)
β (°)	112.047 (5)
V (Å³)	5370.4 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.32 × 0.3 × 0.19

Data collection
Diffractometer	Oxford Diffraction KM-4-CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	18436, 5260, 4788
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.148, 1.11
No. of reflections	5260
No. of parameters	296
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.14, −0.78

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

Cr1—N1	2.136 (3)	Si1—O3	1.6342 (17)
Cr1—N2	2.153 (3)	Si1—O2	1.6370 (17)
Cr1—S1	2.4426 (6)	Si1—O1	1.6480 (17)
S1—Si1	2.0694 (8)

Acknowledgements

The authors thank Dr Anna Dolega for helpful discussions during the preparation of the manuscript.

References

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