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The title compound, [Sn4(C9H12N)4S6]·CHCl3, consists of four [2-(Me2NCH2)C6H4]Sn units bridged by six S atoms along with a disordered solvent mol­ecule. The cage-like structure has two four-membered Sn2S2 rings linked by two S atoms in an Sn4S6 skeleton. The asymmetry of the Sn—S bonds in the four-membered rings is the result of the combined effect of the trans influence of the strong N→ Sn intra­molecular coordination as well as the Sn—S (axial and equatorial) bonds. The Sn atoms are penta­coordinated with a (C,N)SnS3 trigonal bipyramidal core. Owing to inter­molecular H...Ph inter­actions, the mol­ecules are arranged into a polymeric ribbon along the b axis of the monoclinic unit cell. The solvent Cl atoms are disordered over two positions; the site occupancies are 0.58 and 0.42.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051501/ng2339sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051501/ng2339Isup2.hkl
Contains datablock I

CCDC reference: 667203

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.009 Å
  • Disorder in solvent or counterion
  • R factor = 0.045
  • wR factor = 0.085
  • Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.63 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S1 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C37 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 43.00 Perc. PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 9
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 36
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

During our work on hypercoordinated organotin(IV) compounds with the [2-(Me2NCH2)C6H4]Sn fragment (Varga et al., 2001, 2005, 2006), the title compound (I) was isolated as chloroform solvate. It contains two four-membered Sn2S2 rings, with each Sn atom bearing a (C,N)-coordinated organic group. The rings are bridged by two S atoms in a cage structure with a Sn4S6 skeleton (Fig. 1). This type of structure was suggested on the basis of mass spectra as one of the two possible structures for methyltin(IV) sulfide (Dörfelt et al. 1968).

The two four-membered Sn2S2 rings are almost parallel (dihedral angle between the planes generated by Sn1S1Sn2S2 and Sn3S3Sn4S4 atoms is 5.7 Å). They are also twisted from a Sn—Sn axis (the angle between the axis through Sn1Sn2 and Sn3Sn4 is 31.7 Å, Fig.2). The distortion of the skeleton is the result of the strong NSn intramolecular coordination and the difference in the Sn—S bond lengths within the Sn2S2 rings. The asymmetry of the Sn—S—Sn bridge in the Sn2S2 rings [Sn1—S1 = 2.482 (2) Å, Sn1—S2 = 2.381 (2) Å, for the other bonds see Table 1] is the result of the trans influence of the NSn intramolecular coordination and the axial and equatorial positions of the S atoms bound to Sn. These values are either longer or smaller than those of the bonds bridging the four-membered rings [Sn—S range 2.416—2.422 Å].

The Sn atoms are pentacoordinated, with the N and one S atoms in axial positions and two S and the C atom from the organic group occupying the equatorial ones (Table 1).

All the (C,N)SnS3 cores are distorted from the ideal geometry as a consequence of the small 'bite' of the pendant arm ligand [C1—Sn1—N1 = 73.5 (2)°, C10—Sn1—N2 = 70.9 (1)°, C19—Sn3—N3 = 74.2 (2)°, C28—Sn4—N4 = 73.6 (2)°].

The intramolecular NSn interaction induces planar chirality (Varga et al., 2005, 2006) and both RN1RN2RN3RN4 and SN1SN2SN3SN4 isomers are present in the crystal.

Intermolecular H···phenyl interactions between three aromatic H atoms and phenyl rings from the neighboring molecules (H···π range 2.87–3.23 Å, see Extra Table) link isomers of the same type and the solvent molecules in a polymeric double chain (Fig. 3) along b axis.

Chains of different isomers alternate in crystal, with no further interactions between polymers.

Related literature top

For related literature, see: Dörfelt et al. (1968); Varga et al. (2001, 2005, 2006).

Experimental top

A solution of [2-(Me2NCH2)C6H4]SnCl3 (0.25 g, 0.7 mmol) in CH2Cl2 (15 ml) was treated with an aqueous solution of Na2S (0.41 g, 5.25 mmol, 500% excess) and the reaction was stirred for 3 h at room temperature. The organic layer was separated, the water solution was washed with dichloromethane (2x5 ml) and the combined organic phases were dried over anhydrous Na2SO4. After removal of the solvent under vacuum the title compound was isolated as a white crystalline solid (0.19 g, 90%).

Refinement top

All hydrogen atoms were placed in calculated positions using a riding model, with C—H = 0.93–0.97 Å and with Uiso= 1.5Ueq (C) for methyl H and Uiso= 1.2Ueq (C) for aryl H. The methyl groups were allowed to rotate but not to tip. The chloroform molecule is disordered over two orientations related by rotation about its C—H bond, with site occupancy of 42:58 for the Cl atoms. The C—Cl bonds were restrained within 0.01 Å of each other.

Structure description top

During our work on hypercoordinated organotin(IV) compounds with the [2-(Me2NCH2)C6H4]Sn fragment (Varga et al., 2001, 2005, 2006), the title compound (I) was isolated as chloroform solvate. It contains two four-membered Sn2S2 rings, with each Sn atom bearing a (C,N)-coordinated organic group. The rings are bridged by two S atoms in a cage structure with a Sn4S6 skeleton (Fig. 1). This type of structure was suggested on the basis of mass spectra as one of the two possible structures for methyltin(IV) sulfide (Dörfelt et al. 1968).

The two four-membered Sn2S2 rings are almost parallel (dihedral angle between the planes generated by Sn1S1Sn2S2 and Sn3S3Sn4S4 atoms is 5.7 Å). They are also twisted from a Sn—Sn axis (the angle between the axis through Sn1Sn2 and Sn3Sn4 is 31.7 Å, Fig.2). The distortion of the skeleton is the result of the strong NSn intramolecular coordination and the difference in the Sn—S bond lengths within the Sn2S2 rings. The asymmetry of the Sn—S—Sn bridge in the Sn2S2 rings [Sn1—S1 = 2.482 (2) Å, Sn1—S2 = 2.381 (2) Å, for the other bonds see Table 1] is the result of the trans influence of the NSn intramolecular coordination and the axial and equatorial positions of the S atoms bound to Sn. These values are either longer or smaller than those of the bonds bridging the four-membered rings [Sn—S range 2.416—2.422 Å].

The Sn atoms are pentacoordinated, with the N and one S atoms in axial positions and two S and the C atom from the organic group occupying the equatorial ones (Table 1).

All the (C,N)SnS3 cores are distorted from the ideal geometry as a consequence of the small 'bite' of the pendant arm ligand [C1—Sn1—N1 = 73.5 (2)°, C10—Sn1—N2 = 70.9 (1)°, C19—Sn3—N3 = 74.2 (2)°, C28—Sn4—N4 = 73.6 (2)°].

The intramolecular NSn interaction induces planar chirality (Varga et al., 2005, 2006) and both RN1RN2RN3RN4 and SN1SN2SN3SN4 isomers are present in the crystal.

Intermolecular H···phenyl interactions between three aromatic H atoms and phenyl rings from the neighboring molecules (H···π range 2.87–3.23 Å, see Extra Table) link isomers of the same type and the solvent molecules in a polymeric double chain (Fig. 3) along b axis.

Chains of different isomers alternate in crystal, with no further interactions between polymers.

For related literature, see: Dörfelt et al. (1968); Varga et al. (2001, 2005, 2006).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL (Bruker, 2001); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. : View of the title compound showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms as spheres of arbitrary radii. The solvent molecule is omitted for clarity.
[Figure 2] Fig. 2. : Detailed view of the inorganic skeleton of the title compound.
[Figure 3] Fig. 3. : Intermolecular interactions (represented with dashed lines) in crystal structure of the title compound. Symmetry codes: (i) 1 - x, -1/2 + y, 1/2 - z, (ii) 1 - x, 1 - y, 1 - z.
Tetrakis[2-(dimethylaminomethyl)phenyl]-1κC,2κC,3κC,4κC- hexa-µ-sulfido-1:2κ4S:S;1,4κ2S:S;2:3κ2S:S;3:4κ4S:S- tetratin(IV) chloroform solvate top
Crystal data top
[Sn4(C9H12N)4S6]·CHCl3F(000) = 2584
Mr = 1323.27Dx = 1.815 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5287 reflections
a = 18.3436 (16) Åθ = 2.2–26.0°
b = 12.9426 (11) ŵ = 2.50 mm1
c = 20.5064 (17) ÅT = 297 K
β = 95.957 (2)°Block, colourless
V = 4842.2 (7) Å30.22 × 0.20 × 0.15 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
8532 independent reflections
Radiation source: fine-focus sealed tube7847 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SMART; Bruker, 2000)
h = 2121
Tmin = 0.592, Tmax = 0.685k = 1515
45895 measured reflectionsl = 2424
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 1.25 w = 1/[σ2(Fo2) + (0.0212P)2 + 10.3311P]
where P = (Fo2 + 2Fc2)/3
8532 reflections(Δ/σ)max = 0.001
523 parametersΔρmax = 0.65 e Å3
36 restraintsΔρmin = 0.64 e Å3
Crystal data top
[Sn4(C9H12N)4S6]·CHCl3V = 4842.2 (7) Å3
Mr = 1323.27Z = 4
Monoclinic, P21/cMo Kα radiation
a = 18.3436 (16) ŵ = 2.50 mm1
b = 12.9426 (11) ÅT = 297 K
c = 20.5064 (17) Å0.22 × 0.20 × 0.15 mm
β = 95.957 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
8532 independent reflections
Absorption correction: multi-scan
(SMART; Bruker, 2000)
7847 reflections with I > 2σ(I)
Tmin = 0.592, Tmax = 0.685Rint = 0.048
45895 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04536 restraints
wR(F2) = 0.085H-atom parameters constrained
S = 1.25 w = 1/[σ2(Fo2) + (0.0212P)2 + 10.3311P]
where P = (Fo2 + 2Fc2)/3
8532 reflectionsΔρmax = 0.65 e Å3
523 parametersΔρmin = 0.64 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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
xyzUiso*/UeqOcc. (<1)
Sn10.26821 (2)0.41338 (3)0.356993 (18)0.02986 (10)
Sn20.09335 (2)0.32210 (3)0.347054 (18)0.03078 (10)
Sn40.33646 (2)0.12921 (3)0.339185 (18)0.03016 (10)
Sn30.18838 (2)0.06584 (3)0.417327 (18)0.03000 (10)
N10.3557 (3)0.4710 (4)0.4535 (2)0.0386 (12)
N20.0021 (3)0.2856 (4)0.2536 (2)0.0424 (12)
N30.1607 (3)0.0792 (4)0.5356 (2)0.0394 (12)
N40.3635 (3)0.1102 (4)0.2201 (2)0.0467 (13)
S10.17372 (9)0.36588 (14)0.26650 (7)0.0466 (4)
S20.18540 (8)0.38160 (13)0.43677 (7)0.0398 (4)
S30.07148 (8)0.15029 (12)0.38754 (8)0.0416 (4)
S40.22241 (9)0.04969 (13)0.30360 (7)0.0450 (4)
S50.30716 (8)0.13240 (13)0.45431 (7)0.0390 (4)
S60.36809 (8)0.30876 (11)0.32632 (8)0.0367 (3)
C10.3035 (3)0.5660 (4)0.3343 (3)0.0372 (14)
C20.3662 (3)0.6021 (4)0.3702 (3)0.0417 (15)
C30.3921 (4)0.7007 (5)0.3580 (4)0.060 (2)
H30.43510.72440.38110.071*
C40.3551 (6)0.7616 (6)0.3130 (4)0.080 (3)
H40.37240.82790.30650.096*
C50.2928 (6)0.7292 (6)0.2764 (4)0.077 (3)
H50.26850.77240.24500.093*
C60.2660 (4)0.6295 (5)0.2871 (3)0.0534 (18)
H60.22360.60600.26280.064*
C70.4072 (3)0.5336 (5)0.4202 (3)0.0458 (16)
H7A0.43980.48860.39900.055*
H7B0.43660.57550.45210.055*
C80.3183 (4)0.5377 (5)0.4981 (3)0.0530 (17)
H8A0.35420.56950.52930.079*
H8B0.28550.49670.52090.079*
H8C0.29110.59030.47320.079*
C90.3930 (4)0.3866 (5)0.4916 (3)0.0581 (19)
H9A0.41940.34480.46340.087*
H9B0.35740.34490.51050.087*
H9C0.42660.41510.52600.087*
C100.0012 (3)0.4087 (4)0.3667 (3)0.0309 (12)
C110.0674 (3)0.3771 (4)0.3341 (3)0.0374 (14)
C120.1310 (3)0.4284 (5)0.3456 (3)0.0506 (17)
H120.17560.40830.32350.061*
C130.1285 (4)0.5089 (5)0.3895 (3)0.0531 (18)
H130.17160.54210.39770.064*
C140.0630 (4)0.5407 (5)0.4212 (3)0.0487 (17)
H140.06150.59620.45020.058*
C150.0006 (3)0.4906 (4)0.4102 (3)0.0380 (14)
H150.04500.51180.43200.046*
C160.0690 (3)0.2874 (5)0.2873 (3)0.0456 (16)
H16A0.07300.22330.31110.055*
H16B0.11150.29320.25520.055*
C170.0044 (4)0.3707 (6)0.2056 (3)0.0543 (18)
H17A0.04370.35900.17170.082*
H17B0.04120.37370.18670.082*
H17C0.01240.43490.22730.082*
C180.0064 (4)0.1873 (6)0.2197 (4)0.069 (2)
H18A0.03220.18000.18470.103*
H18B0.00420.13130.25020.103*
H18C0.05290.18620.20210.103*
C190.1592 (3)0.0858 (4)0.4449 (3)0.0344 (13)
C200.1201 (3)0.0948 (5)0.4989 (3)0.0395 (14)
C210.0988 (4)0.1911 (5)0.5190 (4)0.0545 (18)
H210.07250.19660.55520.065*
C220.1161 (4)0.2791 (5)0.4860 (4)0.0575 (19)
H220.10120.34360.49970.069*
C230.1555 (4)0.2708 (5)0.4327 (3)0.0518 (17)
H230.16800.33000.41070.062*
C240.1766 (3)0.1755 (5)0.4118 (3)0.0411 (14)
H240.20260.17060.37530.049*
C250.1010 (3)0.0027 (5)0.5347 (3)0.0469 (16)
H25A0.05620.03220.51310.056*
H25B0.09240.01440.57930.056*
C260.1360 (4)0.1810 (5)0.5561 (3)0.0558 (18)
H26A0.12400.17720.60050.084*
H26B0.09340.20160.52790.084*
H26C0.17440.23070.55330.084*
C270.2239 (4)0.0454 (5)0.5806 (3)0.0537 (18)
H27A0.26210.09620.58150.081*
H27B0.24170.01940.56590.081*
H27C0.20920.03730.62390.081*
C280.4388 (3)0.0493 (4)0.3416 (3)0.0372 (14)
C290.4755 (3)0.0569 (5)0.2856 (3)0.0465 (16)
C300.5415 (4)0.0064 (7)0.2849 (4)0.072 (2)
H300.56580.00920.24730.087*
C310.5718 (4)0.0471 (7)0.3373 (5)0.082 (3)
H310.61720.07840.33570.098*
C320.5369 (4)0.0561 (6)0.3930 (5)0.074 (2)
H320.55770.09380.42880.089*
C330.4685 (4)0.0066 (5)0.3947 (4)0.0518 (17)
H330.44350.01200.43170.062*
C340.4429 (4)0.1218 (6)0.2285 (3)0.0556 (19)
H34A0.45540.19380.23640.067*
H34B0.46310.10030.18880.067*
C350.3432 (4)0.0075 (5)0.1938 (3)0.0557 (18)
H35A0.35710.00150.15010.084*
H35B0.29120.00170.19300.084*
H35C0.36800.04450.22120.084*
C360.3280 (5)0.1901 (6)0.1756 (3)0.069 (2)
H36A0.34130.25750.19240.103*
H36B0.27570.18210.17290.103*
H36C0.34400.18230.13280.103*
Cl1A0.2869 (4)0.7495 (10)0.6065 (6)0.133 (6)0.42 (2)
Cl2B0.4358 (4)0.7223 (7)0.6359 (7)0.091 (3)0.58 (2)
Cl3B0.3910 (9)0.8116 (11)0.5126 (3)0.244 (9)0.58 (2)
C370.3710 (3)0.8011 (5)0.5928 (3)0.085 (3)
H370.37880.86400.61910.102*
Cl1B0.2842 (2)0.7498 (6)0.5950 (4)0.102 (3)0.58 (2)
Cl3A0.3707 (5)0.8341 (11)0.5111 (3)0.104 (4)0.42 (2)
Cl2A0.4411 (5)0.7160 (11)0.6163 (8)0.120 (6)0.42 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0271 (2)0.0308 (2)0.0321 (2)0.00056 (16)0.00546 (16)0.00052 (16)
Sn20.0241 (2)0.0353 (2)0.0328 (2)0.00175 (16)0.00235 (16)0.00107 (17)
Sn40.0287 (2)0.0305 (2)0.0328 (2)0.00044 (16)0.01042 (16)0.00009 (16)
Sn30.0254 (2)0.0303 (2)0.0353 (2)0.00136 (16)0.00764 (16)0.00113 (16)
N10.039 (3)0.040 (3)0.037 (3)0.008 (2)0.001 (2)0.001 (2)
N20.036 (3)0.051 (3)0.040 (3)0.003 (2)0.001 (2)0.010 (2)
N30.043 (3)0.038 (3)0.040 (3)0.000 (2)0.016 (2)0.003 (2)
N40.060 (4)0.045 (3)0.038 (3)0.011 (3)0.019 (3)0.001 (2)
S10.0388 (9)0.0720 (12)0.0291 (8)0.0096 (8)0.0040 (7)0.0018 (8)
S20.0299 (8)0.0602 (10)0.0295 (8)0.0075 (7)0.0041 (6)0.0021 (7)
S30.0252 (8)0.0402 (9)0.0597 (10)0.0007 (6)0.0051 (7)0.0093 (7)
S40.0424 (9)0.0602 (11)0.0330 (8)0.0142 (8)0.0075 (7)0.0075 (7)
S50.0310 (8)0.0548 (10)0.0318 (8)0.0092 (7)0.0071 (6)0.0024 (7)
S60.0333 (8)0.0299 (8)0.0500 (9)0.0019 (6)0.0185 (7)0.0007 (7)
C10.046 (4)0.027 (3)0.041 (3)0.001 (3)0.017 (3)0.001 (3)
C20.050 (4)0.033 (3)0.046 (4)0.009 (3)0.023 (3)0.009 (3)
C30.074 (5)0.047 (4)0.061 (5)0.024 (4)0.023 (4)0.010 (4)
C40.129 (8)0.048 (5)0.066 (6)0.013 (5)0.026 (6)0.012 (4)
C50.121 (8)0.049 (5)0.064 (5)0.015 (5)0.022 (5)0.022 (4)
C60.064 (5)0.048 (4)0.051 (4)0.010 (3)0.016 (3)0.011 (3)
C70.035 (3)0.045 (4)0.057 (4)0.012 (3)0.004 (3)0.007 (3)
C80.055 (4)0.062 (4)0.041 (4)0.009 (3)0.001 (3)0.009 (3)
C90.053 (4)0.064 (5)0.053 (4)0.006 (4)0.015 (3)0.008 (4)
C100.027 (3)0.031 (3)0.035 (3)0.005 (2)0.001 (2)0.005 (2)
C110.033 (3)0.036 (3)0.042 (3)0.004 (3)0.003 (3)0.004 (3)
C120.035 (4)0.069 (5)0.047 (4)0.010 (3)0.001 (3)0.005 (4)
C130.039 (4)0.065 (5)0.057 (4)0.029 (3)0.011 (3)0.012 (4)
C140.065 (5)0.044 (4)0.039 (4)0.018 (3)0.015 (3)0.000 (3)
C150.048 (4)0.036 (3)0.030 (3)0.004 (3)0.004 (3)0.005 (3)
C160.035 (3)0.053 (4)0.048 (4)0.008 (3)0.002 (3)0.001 (3)
C170.050 (4)0.075 (5)0.036 (4)0.002 (4)0.002 (3)0.007 (3)
C180.076 (5)0.064 (5)0.062 (5)0.005 (4)0.013 (4)0.026 (4)
C190.028 (3)0.028 (3)0.047 (4)0.001 (2)0.004 (3)0.004 (3)
C200.032 (3)0.043 (4)0.045 (4)0.005 (3)0.006 (3)0.005 (3)
C210.050 (4)0.050 (4)0.065 (5)0.013 (3)0.015 (3)0.017 (4)
C220.072 (5)0.035 (4)0.064 (5)0.015 (3)0.004 (4)0.010 (3)
C230.054 (4)0.035 (4)0.064 (5)0.004 (3)0.007 (4)0.002 (3)
C240.036 (3)0.043 (4)0.042 (4)0.005 (3)0.004 (3)0.000 (3)
C250.043 (4)0.044 (4)0.058 (4)0.003 (3)0.026 (3)0.004 (3)
C260.074 (5)0.043 (4)0.055 (4)0.008 (4)0.025 (4)0.010 (3)
C270.062 (5)0.066 (5)0.033 (3)0.004 (4)0.005 (3)0.002 (3)
C280.032 (3)0.028 (3)0.052 (4)0.001 (2)0.006 (3)0.009 (3)
C290.039 (4)0.047 (4)0.056 (4)0.002 (3)0.020 (3)0.024 (3)
C300.049 (5)0.085 (6)0.085 (6)0.007 (4)0.017 (4)0.038 (5)
C310.048 (5)0.084 (6)0.111 (8)0.027 (4)0.005 (5)0.035 (6)
C320.061 (5)0.050 (5)0.106 (7)0.016 (4)0.020 (5)0.010 (5)
C330.052 (4)0.038 (4)0.067 (5)0.001 (3)0.013 (4)0.003 (3)
C340.061 (5)0.062 (5)0.050 (4)0.013 (4)0.034 (4)0.010 (4)
C350.079 (5)0.053 (4)0.036 (4)0.011 (4)0.011 (3)0.012 (3)
C360.102 (6)0.062 (5)0.041 (4)0.001 (4)0.005 (4)0.010 (4)
Cl1A0.148 (11)0.155 (11)0.112 (7)0.002 (8)0.086 (8)0.033 (7)
Cl2B0.084 (4)0.078 (4)0.108 (6)0.016 (3)0.008 (3)0.019 (4)
Cl3B0.55 (3)0.102 (7)0.095 (6)0.118 (11)0.102 (9)0.011 (5)
C370.122 (8)0.049 (5)0.079 (6)0.003 (5)0.007 (6)0.016 (4)
Cl1B0.066 (4)0.122 (6)0.108 (4)0.036 (4)0.033 (4)0.058 (4)
Cl3A0.107 (8)0.111 (8)0.094 (7)0.007 (5)0.010 (4)0.047 (6)
Cl2A0.070 (6)0.109 (8)0.169 (14)0.027 (5)0.056 (7)0.056 (7)
Geometric parameters (Å, º) top
Sn1—C12.145 (6)C13—H130.9300
Sn1—S22.3810 (15)C14—C151.374 (8)
Sn1—S62.4134 (14)C14—H140.9300
Sn1—S12.4816 (16)C15—H150.9300
Sn1—N12.527 (5)C16—H16A0.9700
Sn2—C102.138 (5)C16—H16B0.9700
Sn2—S12.3935 (16)C17—H17A0.9600
Sn2—S32.4216 (16)C17—H17B0.9600
Sn2—S22.4869 (15)C17—H17C0.9600
Sn2—N22.503 (5)C18—H18A0.9600
Sn4—C282.139 (6)C18—H18B0.9600
Sn4—S42.3774 (16)C18—H18C0.9600
Sn4—S62.4162 (15)C19—C201.386 (8)
Sn4—S52.4753 (15)C19—C241.397 (8)
Sn4—N42.554 (5)C20—C211.381 (8)
Sn3—C192.126 (5)C20—C251.519 (8)
Sn3—S52.3919 (15)C21—C221.379 (9)
Sn3—S32.4278 (15)C21—H210.9300
Sn3—S42.4847 (15)C22—C231.375 (9)
Sn3—N32.536 (5)C22—H220.9300
N1—C71.465 (7)C23—C241.375 (8)
N1—C91.471 (8)C23—H230.9300
N1—C81.477 (8)C24—H240.9300
N2—C181.465 (8)C25—H25A0.9700
N2—C161.469 (7)C25—H25B0.9700
N2—C171.474 (8)C26—H26A0.9600
N3—C261.468 (7)C26—H26B0.9600
N3—C271.472 (8)C26—H26C0.9600
N3—C251.476 (7)C27—H27A0.9600
N4—C341.455 (8)C27—H27B0.9600
N4—C351.468 (8)C27—H27C0.9600
N4—C361.484 (8)C28—C331.372 (9)
C1—C21.381 (8)C28—C291.393 (8)
C1—C61.396 (8)C29—C301.377 (9)
C2—C31.393 (8)C29—C341.514 (9)
C2—C71.498 (9)C30—C311.349 (12)
C3—C41.343 (11)C30—H300.9300
C3—H30.9300C31—C321.370 (12)
C4—C51.366 (12)C31—H310.9300
C4—H40.9300C32—C331.413 (10)
C5—C61.406 (10)C32—H320.9300
C5—H50.9300C33—H330.9300
C6—H60.9300C34—H34A0.9700
C7—H7A0.9700C34—H34B0.9700
C7—H7B0.9700C35—H35A0.9600
C8—H8A0.9600C35—H35B0.9600
C8—H8B0.9600C35—H35C0.9600
C8—H8C0.9600C36—H36A0.9600
C9—H9A0.9600C36—H36B0.9600
C9—H9B0.9600C36—H36C0.9600
C9—H9C0.9600Cl1A—C371.730 (6)
C10—C151.384 (8)Cl2B—C371.736 (6)
C10—C111.386 (8)Cl3B—C371.728 (6)
C11—C121.384 (8)C37—Cl2A1.723 (7)
C11—C161.505 (8)C37—Cl3A1.728 (6)
C12—C131.376 (9)C37—Cl1B1.729 (6)
C12—H120.9300C37—H370.9800
C13—C141.369 (9)
C1—Sn1—S2122.44 (15)C14—C13—H13119.7
C1—Sn1—S6101.89 (15)C12—C13—H13119.7
S2—Sn1—S6129.63 (6)C13—C14—C15119.9 (6)
C1—Sn1—S1105.62 (17)C13—C14—H14120.1
S2—Sn1—S191.44 (5)C15—C14—H14120.1
S6—Sn1—S199.00 (6)C14—C15—C10120.3 (6)
C1—Sn1—N173.5 (2)C14—C15—H15119.8
S2—Sn1—N184.93 (11)C10—C15—H15119.8
S6—Sn1—N186.11 (12)N2—C16—C11110.5 (5)
S1—Sn1—N1174.88 (12)N2—C16—H16A109.5
C10—Sn2—S1125.14 (15)C11—C16—H16A109.5
C10—Sn2—S3104.51 (15)N2—C16—H16B109.5
S1—Sn2—S3126.15 (6)C11—C16—H16B109.5
C10—Sn2—S2101.53 (15)H16A—C16—H16B108.1
S1—Sn2—S291.02 (5)N2—C17—H17A109.5
S3—Sn2—S298.89 (6)N2—C17—H17B109.5
C10—Sn2—N274.15 (18)H17A—C17—H17B109.5
S1—Sn2—N287.02 (12)N2—C17—H17C109.5
S3—Sn2—N287.81 (13)H17A—C17—H17C109.5
S2—Sn2—N2172.83 (13)H17B—C17—H17C109.5
C28—Sn4—S4122.68 (15)N2—C18—H18A109.5
C28—Sn4—S6104.33 (15)N2—C18—H18B109.5
S4—Sn4—S6126.62 (6)H18A—C18—H18B109.5
C28—Sn4—S5105.26 (17)N2—C18—H18C109.5
S4—Sn4—S591.64 (5)H18A—C18—H18C109.5
S6—Sn4—S599.58 (5)H18B—C18—H18C109.5
C28—Sn4—N473.6 (2)C20—C19—C24118.8 (5)
S4—Sn4—N485.24 (12)C20—C19—Sn3117.1 (4)
S6—Sn4—N485.15 (12)C24—C19—Sn3124.1 (4)
S5—Sn4—N4175.26 (12)C21—C20—C19119.9 (6)
C19—Sn3—S5119.64 (15)C21—C20—C25121.3 (6)
C19—Sn3—S3104.01 (15)C19—C20—C25118.8 (5)
S5—Sn3—S3132.02 (6)C22—C21—C20120.9 (6)
C19—Sn3—S4105.44 (16)C22—C21—H21119.6
S5—Sn3—S491.07 (5)C20—C21—H21119.6
S3—Sn3—S495.92 (6)C23—C22—C21119.4 (6)
C19—Sn3—N374.23 (19)C23—C22—H22120.3
S5—Sn3—N386.46 (12)C21—C22—H22120.3
S3—Sn3—N387.17 (12)C22—C23—C24120.4 (6)
S4—Sn3—N3176.87 (12)C22—C23—H23119.8
C7—N1—C9111.8 (5)C24—C23—H23119.8
C7—N1—C8109.2 (5)C23—C24—C19120.5 (6)
C9—N1—C8108.9 (5)C23—C24—H24119.7
C7—N1—Sn1100.8 (3)C19—C24—H24119.7
C9—N1—Sn1114.8 (4)N3—C25—C20110.8 (5)
C8—N1—Sn1111.1 (4)N3—C25—H25A109.5
C18—N2—C16111.8 (5)C20—C25—H25A109.5
C18—N2—C17109.3 (5)N3—C25—H25B109.5
C16—N2—C17109.5 (5)C20—C25—H25B109.5
C18—N2—Sn2115.2 (4)H25A—C25—H25B108.1
C16—N2—Sn2100.9 (3)N3—C26—H26A109.5
C17—N2—Sn2109.9 (4)N3—C26—H26B109.5
C26—N3—C27109.5 (5)H26A—C26—H26B109.5
C26—N3—C25110.8 (5)N3—C26—H26C109.5
C27—N3—C25110.1 (5)H26A—C26—H26C109.5
C26—N3—Sn3115.7 (4)H26B—C26—H26C109.5
C27—N3—Sn3110.9 (3)N3—C27—H27A109.5
C25—N3—Sn399.4 (3)N3—C27—H27B109.5
C34—N4—C35110.5 (5)H27A—C27—H27B109.5
C34—N4—C36111.8 (5)N3—C27—H27C109.5
C35—N4—C36109.1 (5)H27A—C27—H27C109.5
C34—N4—Sn499.7 (4)H27B—C27—H27C109.5
C35—N4—Sn4111.8 (4)C33—C28—C29120.3 (6)
C36—N4—Sn4113.8 (4)C33—C28—Sn4123.2 (5)
Sn2—S1—Sn188.57 (5)C29—C28—Sn4116.5 (5)
Sn1—S2—Sn288.73 (5)C30—C29—C28118.5 (7)
Sn2—S3—Sn3109.04 (6)C30—C29—C34122.1 (6)
Sn4—S4—Sn388.53 (5)C28—C29—C34119.4 (5)
Sn3—S5—Sn488.42 (5)C31—C30—C29121.6 (8)
Sn1—S6—Sn4108.29 (5)C31—C30—H30119.2
C2—C1—C6119.6 (6)C29—C30—H30119.2
C2—C1—Sn1116.7 (4)C30—C31—C32121.2 (8)
C6—C1—Sn1123.7 (5)C30—C31—H31119.4
C1—C2—C3119.7 (6)C32—C31—H31119.4
C1—C2—C7119.7 (5)C31—C32—C33118.4 (8)
C3—C2—C7120.6 (6)C31—C32—H32120.8
C4—C3—C2120.2 (8)C33—C32—H32120.8
C4—C3—H3119.9C28—C33—C32120.0 (7)
C2—C3—H3119.9C28—C33—H33120.0
C3—C4—C5122.1 (8)C32—C33—H33120.0
C3—C4—H4118.9N4—C34—C29110.2 (5)
C5—C4—H4118.9N4—C34—H34A109.6
C4—C5—C6118.8 (8)C29—C34—H34A109.6
C4—C5—H5120.6N4—C34—H34B109.6
C6—C5—H5120.6C29—C34—H34B109.6
C1—C6—C5119.6 (7)H34A—C34—H34B108.1
C1—C6—H6120.2N4—C35—H35A109.5
C5—C6—H6120.2N4—C35—H35B109.5
N1—C7—C2110.1 (5)H35A—C35—H35B109.5
N1—C7—H7A109.6N4—C35—H35C109.5
C2—C7—H7A109.6H35A—C35—H35C109.5
N1—C7—H7B109.6H35B—C35—H35C109.5
C2—C7—H7B109.6N4—C36—H36A109.5
H7A—C7—H7B108.1N4—C36—H36B109.5
N1—C8—H8A109.5H36A—C36—H36B109.5
N1—C8—H8B109.5N4—C36—H36C109.5
H8A—C8—H8B109.5H36A—C36—H36C109.5
N1—C8—H8C109.5H36B—C36—H36C109.5
H8A—C8—H8C109.5Cl2A—C37—Cl3B95.2 (8)
H8B—C8—H8C109.5Cl2A—C37—Cl3A110.9 (5)
N1—C9—H9A109.5Cl2A—C37—Cl1B114.2 (7)
N1—C9—H9B109.5Cl3B—C37—Cl1B110.0 (5)
H9A—C9—H9B109.5Cl3A—C37—Cl1B102.1 (5)
N1—C9—H9C109.5Cl2A—C37—Cl1A111.1 (5)
H9A—C9—H9C109.5Cl3B—C37—Cl1A117.8 (7)
H9B—C9—H9C109.5Cl3A—C37—Cl1A109.9 (5)
C15—C10—C11119.9 (5)Cl3B—C37—Cl2B109.2 (5)
C15—C10—Sn2123.9 (4)Cl3A—C37—Cl2B124.8 (7)
C11—C10—Sn2116.2 (4)Cl1B—C37—Cl2B110.2 (4)
C12—C11—C10119.3 (6)Cl1A—C37—Cl2B105.4 (6)
C12—C11—C16121.2 (6)Cl2A—C37—H37108.3
C10—C11—C16119.5 (5)Cl3B—C37—H37115.1
C13—C12—C11120.2 (6)Cl3A—C37—H37108.3
C13—C12—H12119.9Cl1B—C37—H37112.8
C11—C12—H12119.9Cl1A—C37—H37108.3
C14—C13—C12120.5 (6)Cl2B—C37—H3798.9
C1—Sn1—N1—C734.1 (4)C6—C1—C2—C31.1 (9)
S2—Sn1—N1—C7160.1 (4)Sn1—C1—C2—C3179.9 (5)
S6—Sn1—N1—C769.6 (3)C6—C1—C2—C7179.1 (6)
C1—Sn1—N1—C9154.3 (5)Sn1—C1—C2—C72.1 (7)
S2—Sn1—N1—C979.7 (4)C1—C2—C3—C41.9 (10)
S6—Sn1—N1—C950.7 (4)C7—C2—C3—C4180.0 (7)
C1—Sn1—N1—C881.5 (4)C2—C3—C4—C51.9 (13)
S2—Sn1—N1—C844.5 (4)C3—C4—C5—C61.1 (13)
S6—Sn1—N1—C8174.9 (4)C2—C1—C6—C50.2 (9)
C10—Sn2—N2—C18155.1 (5)Sn1—C1—C6—C5178.9 (5)
S1—Sn2—N2—C1877.0 (5)C4—C5—C6—C10.2 (11)
S3—Sn2—N2—C1849.3 (5)C9—N1—C7—C2166.9 (5)
C10—Sn2—N2—C1634.5 (4)C8—N1—C7—C272.5 (6)
S1—Sn2—N2—C16162.4 (4)Sn1—N1—C7—C244.5 (5)
S3—Sn2—N2—C1671.2 (3)C1—C2—C7—N136.9 (8)
C10—Sn2—N2—C1781.0 (4)C3—C2—C7—N1145.0 (6)
S1—Sn2—N2—C1746.9 (4)S1—Sn2—C10—C1587.2 (5)
S3—Sn2—N2—C17173.3 (4)S3—Sn2—C10—C15114.8 (4)
C19—Sn3—N3—C26153.5 (5)S2—Sn2—C10—C1512.3 (5)
S5—Sn3—N3—C2684.4 (4)N2—Sn2—C10—C15161.8 (5)
S3—Sn3—N3—C2648.1 (4)S1—Sn2—C10—C1194.3 (4)
C19—Sn3—N3—C2781.0 (4)S3—Sn2—C10—C1163.7 (4)
S5—Sn3—N3—C2741.2 (4)S2—Sn2—C10—C11166.2 (4)
S3—Sn3—N3—C27173.6 (4)N2—Sn2—C10—C1119.7 (4)
C19—Sn3—N3—C2534.9 (4)C15—C10—C11—C120.1 (9)
S5—Sn3—N3—C25157.1 (3)Sn2—C10—C11—C12178.6 (4)
S3—Sn3—N3—C2570.5 (3)C15—C10—C11—C16179.5 (5)
C28—Sn4—N4—C3435.5 (4)Sn2—C10—C11—C161.0 (7)
S4—Sn4—N4—C34161.6 (4)C10—C11—C12—C130.8 (9)
S6—Sn4—N4—C3471.0 (4)C16—C11—C12—C13178.8 (6)
C28—Sn4—N4—C3581.2 (5)C11—C12—C13—C141.4 (10)
S4—Sn4—N4—C3544.9 (4)C12—C13—C14—C151.3 (10)
S6—Sn4—N4—C35172.3 (4)C13—C14—C15—C100.6 (9)
C28—Sn4—N4—C36154.7 (5)C11—C10—C15—C140.0 (8)
S4—Sn4—N4—C3679.2 (4)Sn2—C10—C15—C14178.4 (4)
S6—Sn4—N4—C3648.2 (4)C18—N2—C16—C11166.6 (5)
C10—Sn2—S1—Sn1108.61 (18)C17—N2—C16—C1172.2 (6)
S3—Sn2—S1—Sn198.08 (7)Sn2—N2—C16—C1143.6 (5)
S2—Sn2—S1—Sn13.71 (6)C12—C11—C16—N2146.3 (6)
N2—Sn2—S1—Sn1176.82 (12)C10—C11—C16—N234.1 (8)
C1—Sn1—S1—Sn2128.22 (16)S5—Sn3—C19—C2096.0 (4)
S2—Sn1—S1—Sn23.88 (6)S3—Sn3—C19—C2063.3 (5)
S6—Sn1—S1—Sn2126.66 (5)S4—Sn3—C19—C20163.7 (4)
C1—Sn1—S2—Sn2113.3 (2)N3—Sn3—C19—C2019.6 (4)
S6—Sn1—S2—Sn299.21 (7)S5—Sn3—C19—C2484.3 (5)
S1—Sn1—S2—Sn23.73 (6)S3—Sn3—C19—C24116.3 (5)
N1—Sn1—S2—Sn2179.89 (12)S4—Sn3—C19—C2416.0 (5)
C10—Sn2—S2—Sn1130.11 (15)N3—Sn3—C19—C24160.8 (5)
S1—Sn2—S2—Sn13.87 (6)C24—C19—C20—C210.3 (9)
S3—Sn2—S2—Sn1122.99 (5)Sn3—C19—C20—C21179.4 (5)
C10—Sn2—S3—Sn3153.56 (16)C24—C19—C20—C25179.7 (5)
S1—Sn2—S3—Sn348.74 (9)Sn3—C19—C20—C250.1 (7)
S2—Sn2—S3—Sn349.11 (7)C19—C20—C21—C220.2 (10)
N2—Sn2—S3—Sn3133.43 (13)C25—C20—C21—C22179.6 (6)
C19—Sn3—S3—Sn2176.05 (17)C20—C21—C22—C230.5 (11)
S5—Sn3—S3—Sn228.32 (10)C21—C22—C23—C241.0 (11)
S4—Sn3—S3—Sn268.48 (7)C22—C23—C24—C190.9 (10)
N3—Sn3—S3—Sn2110.98 (12)C20—C19—C24—C230.2 (9)
C28—Sn4—S4—Sn3113.7 (2)Sn3—C19—C24—C23179.9 (4)
S6—Sn4—S4—Sn398.85 (6)C26—N3—C25—C20166.8 (5)
S5—Sn4—S4—Sn34.37 (6)C27—N3—C25—C2071.8 (6)
N4—Sn4—S4—Sn3179.21 (13)Sn3—N3—C25—C2044.6 (5)
C19—Sn3—S4—Sn4125.75 (16)C21—C20—C25—N3144.4 (6)
S5—Sn3—S4—Sn44.53 (6)C19—C20—C25—N336.2 (8)
S3—Sn3—S4—Sn4127.93 (6)S4—Sn4—C28—C3388.6 (5)
C19—Sn3—S5—Sn4112.83 (18)S6—Sn4—C28—C33117.8 (5)
S3—Sn3—S5—Sn494.60 (7)S5—Sn4—C28—C3313.5 (5)
S4—Sn3—S5—Sn44.35 (6)N4—Sn4—C28—C33161.7 (5)
N3—Sn3—S5—Sn4177.57 (12)S4—Sn4—C28—C2991.8 (4)
C28—Sn4—S5—Sn3129.13 (16)S6—Sn4—C28—C2961.8 (4)
S4—Sn4—S5—Sn34.54 (6)S5—Sn4—C28—C29166.1 (4)
S6—Sn4—S5—Sn3123.04 (5)N4—Sn4—C28—C2918.7 (4)
C1—Sn1—S6—Sn4175.42 (17)C33—C28—C29—C300.6 (9)
S2—Sn1—S6—Sn432.20 (10)Sn4—C28—C29—C30179.7 (5)
S1—Sn1—S6—Sn467.25 (7)C33—C28—C29—C34178.1 (6)
N1—Sn1—S6—Sn4112.33 (12)Sn4—C28—C29—C341.5 (7)
C28—Sn4—S6—Sn1162.15 (17)C28—C29—C30—C312.0 (11)
S4—Sn4—S6—Sn145.73 (9)C34—C29—C30—C31176.7 (7)
S5—Sn4—S6—Sn153.57 (7)C29—C30—C31—C322.1 (13)
N4—Sn4—S6—Sn1126.13 (14)C30—C31—C32—C330.8 (13)
S2—Sn1—C1—C290.6 (4)C29—C28—C33—C320.6 (9)
S6—Sn1—C1—C264.4 (4)Sn4—C28—C33—C32179.0 (5)
S1—Sn1—C1—C2167.4 (4)C31—C32—C33—C280.5 (11)
N1—Sn1—C1—C217.9 (4)C35—N4—C34—C2971.9 (6)
S2—Sn1—C1—C688.2 (5)C36—N4—C34—C29166.5 (5)
S6—Sn1—C1—C6116.8 (5)Sn4—N4—C34—C2945.8 (5)
S1—Sn1—C1—C613.9 (5)C30—C29—C34—N4143.1 (6)
N1—Sn1—C1—C6160.9 (5)C28—C29—C34—N438.2 (8)

Experimental details

Crystal data
Chemical formula[Sn4(C9H12N)4S6]·CHCl3
Mr1323.27
Crystal system, space groupMonoclinic, P21/c
Temperature (K)297
a, b, c (Å)18.3436 (16), 12.9426 (11), 20.5064 (17)
β (°) 95.957 (2)
V3)4842.2 (7)
Z4
Radiation typeMo Kα
µ (mm1)2.50
Crystal size (mm)0.22 × 0.20 × 0.15
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SMART; Bruker, 2000)
Tmin, Tmax0.592, 0.685
No. of measured, independent and
observed [I > 2σ(I)] reflections
45895, 8532, 7847
Rint0.048
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.085, 1.25
No. of reflections8532
No. of parameters523
No. of restraints36
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0212P)2 + 10.3311P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)0.65, 0.64

Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2000), SHELXTL (Bruker, 2001), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2007).

X—H···π-ring interactions. Cg1 is a centroid of the benzene ring C1–C6, Cg2 is a centroid of the benzene ring C28–C33. top
Y—X···CgX—HH···CgX···CgX—H···Cg
C30—H30···Cg1i0.933.233.98 (1)139
C37—H37···Cg2ii0.982.873.61 (1)133
Symmetry codes: (i) 1-x, -1/2+y, 1/2-z, (ii) 1-x, 1-y, 1-z
 

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