Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051501/ng2339sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051501/ng2339Isup2.hkl |
CCDC reference: 667203
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%).
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.
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 N→Sn 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 N→Sn 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 N→Sn 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).
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).
[Sn4(C9H12N)4S6]·CHCl3 | F(000) = 2584 |
Mr = 1323.27 | Dx = 1.815 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5287 reflections |
a = 18.3436 (16) Å | θ = 2.2–26.0° |
b = 12.9426 (11) Å | µ = 2.50 mm−1 |
c = 20.5064 (17) Å | T = 297 K |
β = 95.957 (2)° | Block, colourless |
V = 4842.2 (7) Å3 | 0.22 × 0.20 × 0.15 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 8532 independent reflections |
Radiation source: fine-focus sealed tube | 7847 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SMART; Bruker, 2000) | h = −21→21 |
Tmin = 0.592, Tmax = 0.685 | k = −15→15 |
45895 measured reflections | l = −24→24 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H-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 parameters | Δρmax = 0.65 e Å−3 |
36 restraints | Δρmin = −0.64 e Å−3 |
[Sn4(C9H12N)4S6]·CHCl3 | V = 4842.2 (7) Å3 |
Mr = 1323.27 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 18.3436 (16) Å | µ = 2.50 mm−1 |
b = 12.9426 (11) Å | T = 297 K |
c = 20.5064 (17) Å | 0.22 × 0.20 × 0.15 mm |
β = 95.957 (2)° |
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 = 0.685 | Rint = 0.048 |
45895 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 36 restraints |
wR(F2) = 0.085 | H-atom parameters constrained |
S = 1.25 | w = 1/[σ2(Fo2) + (0.0212P)2 + 10.3311P] where P = (Fo2 + 2Fc2)/3 |
8532 reflections | Δρmax = 0.65 e Å−3 |
523 parameters | Δρmin = −0.64 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Sn1 | 0.26821 (2) | 0.41338 (3) | 0.356993 (18) | 0.02986 (10) | |
Sn2 | 0.09335 (2) | 0.32210 (3) | 0.347054 (18) | 0.03078 (10) | |
Sn4 | 0.33646 (2) | 0.12921 (3) | 0.339185 (18) | 0.03016 (10) | |
Sn3 | 0.18838 (2) | 0.06584 (3) | 0.417327 (18) | 0.03000 (10) | |
N1 | 0.3557 (3) | 0.4710 (4) | 0.4535 (2) | 0.0386 (12) | |
N2 | −0.0021 (3) | 0.2856 (4) | 0.2536 (2) | 0.0424 (12) | |
N3 | 0.1607 (3) | 0.0792 (4) | 0.5356 (2) | 0.0394 (12) | |
N4 | 0.3635 (3) | 0.1102 (4) | 0.2201 (2) | 0.0467 (13) | |
S1 | 0.17372 (9) | 0.36588 (14) | 0.26650 (7) | 0.0466 (4) | |
S2 | 0.18540 (8) | 0.38160 (13) | 0.43677 (7) | 0.0398 (4) | |
S3 | 0.07148 (8) | 0.15029 (12) | 0.38754 (8) | 0.0416 (4) | |
S4 | 0.22241 (9) | 0.04969 (13) | 0.30360 (7) | 0.0450 (4) | |
S5 | 0.30716 (8) | 0.13240 (13) | 0.45431 (7) | 0.0390 (4) | |
S6 | 0.36809 (8) | 0.30876 (11) | 0.32632 (8) | 0.0367 (3) | |
C1 | 0.3035 (3) | 0.5660 (4) | 0.3343 (3) | 0.0372 (14) | |
C2 | 0.3662 (3) | 0.6021 (4) | 0.3702 (3) | 0.0417 (15) | |
C3 | 0.3921 (4) | 0.7007 (5) | 0.3580 (4) | 0.060 (2) | |
H3 | 0.4351 | 0.7244 | 0.3811 | 0.071* | |
C4 | 0.3551 (6) | 0.7616 (6) | 0.3130 (4) | 0.080 (3) | |
H4 | 0.3724 | 0.8279 | 0.3065 | 0.096* | |
C5 | 0.2928 (6) | 0.7292 (6) | 0.2764 (4) | 0.077 (3) | |
H5 | 0.2685 | 0.7724 | 0.2450 | 0.093* | |
C6 | 0.2660 (4) | 0.6295 (5) | 0.2871 (3) | 0.0534 (18) | |
H6 | 0.2236 | 0.6060 | 0.2628 | 0.064* | |
C7 | 0.4072 (3) | 0.5336 (5) | 0.4202 (3) | 0.0458 (16) | |
H7A | 0.4398 | 0.4886 | 0.3990 | 0.055* | |
H7B | 0.4366 | 0.5755 | 0.4521 | 0.055* | |
C8 | 0.3183 (4) | 0.5377 (5) | 0.4981 (3) | 0.0530 (17) | |
H8A | 0.3542 | 0.5695 | 0.5293 | 0.079* | |
H8B | 0.2855 | 0.4967 | 0.5209 | 0.079* | |
H8C | 0.2911 | 0.5903 | 0.4732 | 0.079* | |
C9 | 0.3930 (4) | 0.3866 (5) | 0.4916 (3) | 0.0581 (19) | |
H9A | 0.4194 | 0.3448 | 0.4634 | 0.087* | |
H9B | 0.3574 | 0.3449 | 0.5105 | 0.087* | |
H9C | 0.4266 | 0.4151 | 0.5260 | 0.087* | |
C10 | −0.0012 (3) | 0.4087 (4) | 0.3667 (3) | 0.0309 (12) | |
C11 | −0.0674 (3) | 0.3771 (4) | 0.3341 (3) | 0.0374 (14) | |
C12 | −0.1310 (3) | 0.4284 (5) | 0.3456 (3) | 0.0506 (17) | |
H12 | −0.1756 | 0.4083 | 0.3235 | 0.061* | |
C13 | −0.1285 (4) | 0.5089 (5) | 0.3895 (3) | 0.0531 (18) | |
H13 | −0.1716 | 0.5421 | 0.3977 | 0.064* | |
C14 | −0.0630 (4) | 0.5407 (5) | 0.4212 (3) | 0.0487 (17) | |
H14 | −0.0615 | 0.5962 | 0.4502 | 0.058* | |
C15 | 0.0006 (3) | 0.4906 (4) | 0.4102 (3) | 0.0380 (14) | |
H15 | 0.0450 | 0.5118 | 0.4320 | 0.046* | |
C16 | −0.0690 (3) | 0.2874 (5) | 0.2873 (3) | 0.0456 (16) | |
H16A | −0.0730 | 0.2233 | 0.3111 | 0.055* | |
H16B | −0.1115 | 0.2932 | 0.2552 | 0.055* | |
C17 | −0.0044 (4) | 0.3707 (6) | 0.2056 (3) | 0.0543 (18) | |
H17A | −0.0437 | 0.3590 | 0.1717 | 0.082* | |
H17B | 0.0412 | 0.3737 | 0.1867 | 0.082* | |
H17C | −0.0124 | 0.4349 | 0.2273 | 0.082* | |
C18 | 0.0064 (4) | 0.1873 (6) | 0.2197 (4) | 0.069 (2) | |
H18A | −0.0322 | 0.1800 | 0.1847 | 0.103* | |
H18B | 0.0042 | 0.1313 | 0.2502 | 0.103* | |
H18C | 0.0529 | 0.1862 | 0.2021 | 0.103* | |
C19 | 0.1592 (3) | −0.0858 (4) | 0.4449 (3) | 0.0344 (13) | |
C20 | 0.1201 (3) | −0.0948 (5) | 0.4989 (3) | 0.0395 (14) | |
C21 | 0.0988 (4) | −0.1911 (5) | 0.5190 (4) | 0.0545 (18) | |
H21 | 0.0725 | −0.1966 | 0.5552 | 0.065* | |
C22 | 0.1161 (4) | −0.2791 (5) | 0.4860 (4) | 0.0575 (19) | |
H22 | 0.1012 | −0.3436 | 0.4997 | 0.069* | |
C23 | 0.1555 (4) | −0.2708 (5) | 0.4327 (3) | 0.0518 (17) | |
H23 | 0.1680 | −0.3300 | 0.4107 | 0.062* | |
C24 | 0.1766 (3) | −0.1755 (5) | 0.4118 (3) | 0.0411 (14) | |
H24 | 0.2026 | −0.1706 | 0.3753 | 0.049* | |
C25 | 0.1010 (3) | 0.0027 (5) | 0.5347 (3) | 0.0469 (16) | |
H25A | 0.0562 | 0.0322 | 0.5131 | 0.056* | |
H25B | 0.0924 | −0.0144 | 0.5793 | 0.056* | |
C26 | 0.1360 (4) | 0.1810 (5) | 0.5561 (3) | 0.0558 (18) | |
H26A | 0.1240 | 0.1772 | 0.6005 | 0.084* | |
H26B | 0.0934 | 0.2016 | 0.5279 | 0.084* | |
H26C | 0.1744 | 0.2307 | 0.5533 | 0.084* | |
C27 | 0.2239 (4) | 0.0454 (5) | 0.5806 (3) | 0.0537 (18) | |
H27A | 0.2621 | 0.0962 | 0.5815 | 0.081* | |
H27B | 0.2417 | −0.0194 | 0.5659 | 0.081* | |
H27C | 0.2092 | 0.0373 | 0.6239 | 0.081* | |
C28 | 0.4388 (3) | 0.0493 (4) | 0.3416 (3) | 0.0372 (14) | |
C29 | 0.4755 (3) | 0.0569 (5) | 0.2856 (3) | 0.0465 (16) | |
C30 | 0.5415 (4) | 0.0064 (7) | 0.2849 (4) | 0.072 (2) | |
H30 | 0.5658 | 0.0092 | 0.2473 | 0.087* | |
C31 | 0.5718 (4) | −0.0471 (7) | 0.3373 (5) | 0.082 (3) | |
H31 | 0.6172 | −0.0784 | 0.3357 | 0.098* | |
C32 | 0.5369 (4) | −0.0561 (6) | 0.3930 (5) | 0.074 (2) | |
H32 | 0.5577 | −0.0938 | 0.4288 | 0.089* | |
C33 | 0.4685 (4) | −0.0066 (5) | 0.3947 (4) | 0.0518 (17) | |
H33 | 0.4435 | −0.0120 | 0.4317 | 0.062* | |
C34 | 0.4429 (4) | 0.1218 (6) | 0.2285 (3) | 0.0556 (19) | |
H34A | 0.4554 | 0.1938 | 0.2364 | 0.067* | |
H34B | 0.4631 | 0.1003 | 0.1888 | 0.067* | |
C35 | 0.3432 (4) | 0.0075 (5) | 0.1938 (3) | 0.0557 (18) | |
H35A | 0.3571 | 0.0015 | 0.1501 | 0.084* | |
H35B | 0.2912 | −0.0017 | 0.1930 | 0.084* | |
H35C | 0.3680 | −0.0445 | 0.2212 | 0.084* | |
C36 | 0.3280 (5) | 0.1901 (6) | 0.1756 (3) | 0.069 (2) | |
H36A | 0.3413 | 0.2575 | 0.1924 | 0.103* | |
H36B | 0.2757 | 0.1821 | 0.1729 | 0.103* | |
H36C | 0.3440 | 0.1823 | 0.1328 | 0.103* | |
Cl1A | 0.2869 (4) | 0.7495 (10) | 0.6065 (6) | 0.133 (6) | 0.42 (2) |
Cl2B | 0.4358 (4) | 0.7223 (7) | 0.6359 (7) | 0.091 (3) | 0.58 (2) |
Cl3B | 0.3910 (9) | 0.8116 (11) | 0.5126 (3) | 0.244 (9) | 0.58 (2) |
C37 | 0.3710 (3) | 0.8011 (5) | 0.5928 (3) | 0.085 (3) | |
H37 | 0.3788 | 0.8640 | 0.6191 | 0.102* | |
Cl1B | 0.2842 (2) | 0.7498 (6) | 0.5950 (4) | 0.102 (3) | 0.58 (2) |
Cl3A | 0.3707 (5) | 0.8341 (11) | 0.5111 (3) | 0.104 (4) | 0.42 (2) |
Cl2A | 0.4411 (5) | 0.7160 (11) | 0.6163 (8) | 0.120 (6) | 0.42 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0271 (2) | 0.0308 (2) | 0.0321 (2) | −0.00056 (16) | 0.00546 (16) | 0.00052 (16) |
Sn2 | 0.0241 (2) | 0.0353 (2) | 0.0328 (2) | 0.00175 (16) | 0.00235 (16) | −0.00107 (17) |
Sn4 | 0.0287 (2) | 0.0305 (2) | 0.0328 (2) | −0.00044 (16) | 0.01042 (16) | 0.00009 (16) |
Sn3 | 0.0254 (2) | 0.0303 (2) | 0.0353 (2) | −0.00136 (16) | 0.00764 (16) | 0.00113 (16) |
N1 | 0.039 (3) | 0.040 (3) | 0.037 (3) | −0.008 (2) | 0.001 (2) | −0.001 (2) |
N2 | 0.036 (3) | 0.051 (3) | 0.040 (3) | 0.003 (2) | −0.001 (2) | −0.010 (2) |
N3 | 0.043 (3) | 0.038 (3) | 0.040 (3) | 0.000 (2) | 0.016 (2) | −0.003 (2) |
N4 | 0.060 (4) | 0.045 (3) | 0.038 (3) | −0.011 (3) | 0.019 (3) | −0.001 (2) |
S1 | 0.0388 (9) | 0.0720 (12) | 0.0291 (8) | −0.0096 (8) | 0.0040 (7) | −0.0018 (8) |
S2 | 0.0299 (8) | 0.0602 (10) | 0.0295 (8) | −0.0075 (7) | 0.0041 (6) | −0.0021 (7) |
S3 | 0.0252 (8) | 0.0402 (9) | 0.0597 (10) | −0.0007 (6) | 0.0051 (7) | 0.0093 (7) |
S4 | 0.0424 (9) | 0.0602 (11) | 0.0330 (8) | −0.0142 (8) | 0.0075 (7) | −0.0075 (7) |
S5 | 0.0310 (8) | 0.0548 (10) | 0.0318 (8) | −0.0092 (7) | 0.0071 (6) | −0.0024 (7) |
S6 | 0.0333 (8) | 0.0299 (8) | 0.0500 (9) | −0.0019 (6) | 0.0185 (7) | −0.0007 (7) |
C1 | 0.046 (4) | 0.027 (3) | 0.041 (3) | 0.001 (3) | 0.017 (3) | 0.001 (3) |
C2 | 0.050 (4) | 0.033 (3) | 0.046 (4) | −0.009 (3) | 0.023 (3) | −0.009 (3) |
C3 | 0.074 (5) | 0.047 (4) | 0.061 (5) | −0.024 (4) | 0.023 (4) | −0.010 (4) |
C4 | 0.129 (8) | 0.048 (5) | 0.066 (6) | −0.013 (5) | 0.026 (6) | 0.012 (4) |
C5 | 0.121 (8) | 0.049 (5) | 0.064 (5) | 0.015 (5) | 0.022 (5) | 0.022 (4) |
C6 | 0.064 (5) | 0.048 (4) | 0.051 (4) | 0.010 (3) | 0.016 (3) | 0.011 (3) |
C7 | 0.035 (3) | 0.045 (4) | 0.057 (4) | −0.012 (3) | 0.004 (3) | −0.007 (3) |
C8 | 0.055 (4) | 0.062 (4) | 0.041 (4) | −0.009 (3) | 0.001 (3) | −0.009 (3) |
C9 | 0.053 (4) | 0.064 (5) | 0.053 (4) | −0.006 (4) | −0.015 (3) | 0.008 (4) |
C10 | 0.027 (3) | 0.031 (3) | 0.035 (3) | 0.005 (2) | 0.001 (2) | 0.005 (2) |
C11 | 0.033 (3) | 0.036 (3) | 0.042 (3) | 0.004 (3) | 0.003 (3) | 0.004 (3) |
C12 | 0.035 (4) | 0.069 (5) | 0.047 (4) | 0.010 (3) | 0.001 (3) | 0.005 (4) |
C13 | 0.039 (4) | 0.065 (5) | 0.057 (4) | 0.029 (3) | 0.011 (3) | 0.012 (4) |
C14 | 0.065 (5) | 0.044 (4) | 0.039 (4) | 0.018 (3) | 0.015 (3) | 0.000 (3) |
C15 | 0.048 (4) | 0.036 (3) | 0.030 (3) | 0.004 (3) | 0.004 (3) | 0.005 (3) |
C16 | 0.035 (3) | 0.053 (4) | 0.048 (4) | −0.008 (3) | −0.002 (3) | −0.001 (3) |
C17 | 0.050 (4) | 0.075 (5) | 0.036 (4) | 0.002 (4) | −0.002 (3) | 0.007 (3) |
C18 | 0.076 (5) | 0.064 (5) | 0.062 (5) | 0.005 (4) | −0.013 (4) | −0.026 (4) |
C19 | 0.028 (3) | 0.028 (3) | 0.047 (4) | −0.001 (2) | 0.004 (3) | 0.004 (3) |
C20 | 0.032 (3) | 0.043 (4) | 0.045 (4) | −0.005 (3) | 0.006 (3) | 0.005 (3) |
C21 | 0.050 (4) | 0.050 (4) | 0.065 (5) | −0.013 (3) | 0.015 (3) | 0.017 (4) |
C22 | 0.072 (5) | 0.035 (4) | 0.064 (5) | −0.015 (3) | 0.004 (4) | 0.010 (3) |
C23 | 0.054 (4) | 0.035 (4) | 0.064 (5) | −0.004 (3) | −0.007 (4) | −0.002 (3) |
C24 | 0.036 (3) | 0.043 (4) | 0.042 (4) | 0.005 (3) | −0.004 (3) | 0.000 (3) |
C25 | 0.043 (4) | 0.044 (4) | 0.058 (4) | −0.003 (3) | 0.026 (3) | 0.004 (3) |
C26 | 0.074 (5) | 0.043 (4) | 0.055 (4) | 0.008 (4) | 0.025 (4) | −0.010 (3) |
C27 | 0.062 (5) | 0.066 (5) | 0.033 (3) | −0.004 (4) | 0.005 (3) | 0.002 (3) |
C28 | 0.032 (3) | 0.028 (3) | 0.052 (4) | 0.001 (2) | 0.006 (3) | −0.009 (3) |
C29 | 0.039 (4) | 0.047 (4) | 0.056 (4) | −0.002 (3) | 0.020 (3) | −0.024 (3) |
C30 | 0.049 (5) | 0.085 (6) | 0.085 (6) | 0.007 (4) | 0.017 (4) | −0.038 (5) |
C31 | 0.048 (5) | 0.084 (6) | 0.111 (8) | 0.027 (4) | −0.005 (5) | −0.035 (6) |
C32 | 0.061 (5) | 0.050 (5) | 0.106 (7) | 0.016 (4) | −0.020 (5) | −0.010 (5) |
C33 | 0.052 (4) | 0.038 (4) | 0.067 (5) | −0.001 (3) | 0.013 (4) | −0.003 (3) |
C34 | 0.061 (5) | 0.062 (5) | 0.050 (4) | −0.013 (4) | 0.034 (4) | −0.010 (4) |
C35 | 0.079 (5) | 0.053 (4) | 0.036 (4) | −0.011 (4) | 0.011 (3) | −0.012 (3) |
C36 | 0.102 (6) | 0.062 (5) | 0.041 (4) | 0.001 (4) | 0.005 (4) | 0.010 (4) |
Cl1A | 0.148 (11) | 0.155 (11) | 0.112 (7) | 0.002 (8) | 0.086 (8) | 0.033 (7) |
Cl2B | 0.084 (4) | 0.078 (4) | 0.108 (6) | −0.016 (3) | −0.008 (3) | −0.019 (4) |
Cl3B | 0.55 (3) | 0.102 (7) | 0.095 (6) | −0.118 (11) | 0.102 (9) | −0.011 (5) |
C37 | 0.122 (8) | 0.049 (5) | 0.079 (6) | −0.003 (5) | −0.007 (6) | −0.016 (4) |
Cl1B | 0.066 (4) | 0.122 (6) | 0.108 (4) | 0.036 (4) | −0.033 (4) | −0.058 (4) |
Cl3A | 0.107 (8) | 0.111 (8) | 0.094 (7) | −0.007 (5) | 0.010 (4) | 0.047 (6) |
Cl2A | 0.070 (6) | 0.109 (8) | 0.169 (14) | 0.027 (5) | −0.056 (7) | −0.056 (7) |
Sn1—C1 | 2.145 (6) | C13—H13 | 0.9300 |
Sn1—S2 | 2.3810 (15) | C14—C15 | 1.374 (8) |
Sn1—S6 | 2.4134 (14) | C14—H14 | 0.9300 |
Sn1—S1 | 2.4816 (16) | C15—H15 | 0.9300 |
Sn1—N1 | 2.527 (5) | C16—H16A | 0.9700 |
Sn2—C10 | 2.138 (5) | C16—H16B | 0.9700 |
Sn2—S1 | 2.3935 (16) | C17—H17A | 0.9600 |
Sn2—S3 | 2.4216 (16) | C17—H17B | 0.9600 |
Sn2—S2 | 2.4869 (15) | C17—H17C | 0.9600 |
Sn2—N2 | 2.503 (5) | C18—H18A | 0.9600 |
Sn4—C28 | 2.139 (6) | C18—H18B | 0.9600 |
Sn4—S4 | 2.3774 (16) | C18—H18C | 0.9600 |
Sn4—S6 | 2.4162 (15) | C19—C20 | 1.386 (8) |
Sn4—S5 | 2.4753 (15) | C19—C24 | 1.397 (8) |
Sn4—N4 | 2.554 (5) | C20—C21 | 1.381 (8) |
Sn3—C19 | 2.126 (5) | C20—C25 | 1.519 (8) |
Sn3—S5 | 2.3919 (15) | C21—C22 | 1.379 (9) |
Sn3—S3 | 2.4278 (15) | C21—H21 | 0.9300 |
Sn3—S4 | 2.4847 (15) | C22—C23 | 1.375 (9) |
Sn3—N3 | 2.536 (5) | C22—H22 | 0.9300 |
N1—C7 | 1.465 (7) | C23—C24 | 1.375 (8) |
N1—C9 | 1.471 (8) | C23—H23 | 0.9300 |
N1—C8 | 1.477 (8) | C24—H24 | 0.9300 |
N2—C18 | 1.465 (8) | C25—H25A | 0.9700 |
N2—C16 | 1.469 (7) | C25—H25B | 0.9700 |
N2—C17 | 1.474 (8) | C26—H26A | 0.9600 |
N3—C26 | 1.468 (7) | C26—H26B | 0.9600 |
N3—C27 | 1.472 (8) | C26—H26C | 0.9600 |
N3—C25 | 1.476 (7) | C27—H27A | 0.9600 |
N4—C34 | 1.455 (8) | C27—H27B | 0.9600 |
N4—C35 | 1.468 (8) | C27—H27C | 0.9600 |
N4—C36 | 1.484 (8) | C28—C33 | 1.372 (9) |
C1—C2 | 1.381 (8) | C28—C29 | 1.393 (8) |
C1—C6 | 1.396 (8) | C29—C30 | 1.377 (9) |
C2—C3 | 1.393 (8) | C29—C34 | 1.514 (9) |
C2—C7 | 1.498 (9) | C30—C31 | 1.349 (12) |
C3—C4 | 1.343 (11) | C30—H30 | 0.9300 |
C3—H3 | 0.9300 | C31—C32 | 1.370 (12) |
C4—C5 | 1.366 (12) | C31—H31 | 0.9300 |
C4—H4 | 0.9300 | C32—C33 | 1.413 (10) |
C5—C6 | 1.406 (10) | C32—H32 | 0.9300 |
C5—H5 | 0.9300 | C33—H33 | 0.9300 |
C6—H6 | 0.9300 | C34—H34A | 0.9700 |
C7—H7A | 0.9700 | C34—H34B | 0.9700 |
C7—H7B | 0.9700 | C35—H35A | 0.9600 |
C8—H8A | 0.9600 | C35—H35B | 0.9600 |
C8—H8B | 0.9600 | C35—H35C | 0.9600 |
C8—H8C | 0.9600 | C36—H36A | 0.9600 |
C9—H9A | 0.9600 | C36—H36B | 0.9600 |
C9—H9B | 0.9600 | C36—H36C | 0.9600 |
C9—H9C | 0.9600 | Cl1A—C37 | 1.730 (6) |
C10—C15 | 1.384 (8) | Cl2B—C37 | 1.736 (6) |
C10—C11 | 1.386 (8) | Cl3B—C37 | 1.728 (6) |
C11—C12 | 1.384 (8) | C37—Cl2A | 1.723 (7) |
C11—C16 | 1.505 (8) | C37—Cl3A | 1.728 (6) |
C12—C13 | 1.376 (9) | C37—Cl1B | 1.729 (6) |
C12—H12 | 0.9300 | C37—H37 | 0.9800 |
C13—C14 | 1.369 (9) | ||
C1—Sn1—S2 | 122.44 (15) | C14—C13—H13 | 119.7 |
C1—Sn1—S6 | 101.89 (15) | C12—C13—H13 | 119.7 |
S2—Sn1—S6 | 129.63 (6) | C13—C14—C15 | 119.9 (6) |
C1—Sn1—S1 | 105.62 (17) | C13—C14—H14 | 120.1 |
S2—Sn1—S1 | 91.44 (5) | C15—C14—H14 | 120.1 |
S6—Sn1—S1 | 99.00 (6) | C14—C15—C10 | 120.3 (6) |
C1—Sn1—N1 | 73.5 (2) | C14—C15—H15 | 119.8 |
S2—Sn1—N1 | 84.93 (11) | C10—C15—H15 | 119.8 |
S6—Sn1—N1 | 86.11 (12) | N2—C16—C11 | 110.5 (5) |
S1—Sn1—N1 | 174.88 (12) | N2—C16—H16A | 109.5 |
C10—Sn2—S1 | 125.14 (15) | C11—C16—H16A | 109.5 |
C10—Sn2—S3 | 104.51 (15) | N2—C16—H16B | 109.5 |
S1—Sn2—S3 | 126.15 (6) | C11—C16—H16B | 109.5 |
C10—Sn2—S2 | 101.53 (15) | H16A—C16—H16B | 108.1 |
S1—Sn2—S2 | 91.02 (5) | N2—C17—H17A | 109.5 |
S3—Sn2—S2 | 98.89 (6) | N2—C17—H17B | 109.5 |
C10—Sn2—N2 | 74.15 (18) | H17A—C17—H17B | 109.5 |
S1—Sn2—N2 | 87.02 (12) | N2—C17—H17C | 109.5 |
S3—Sn2—N2 | 87.81 (13) | H17A—C17—H17C | 109.5 |
S2—Sn2—N2 | 172.83 (13) | H17B—C17—H17C | 109.5 |
C28—Sn4—S4 | 122.68 (15) | N2—C18—H18A | 109.5 |
C28—Sn4—S6 | 104.33 (15) | N2—C18—H18B | 109.5 |
S4—Sn4—S6 | 126.62 (6) | H18A—C18—H18B | 109.5 |
C28—Sn4—S5 | 105.26 (17) | N2—C18—H18C | 109.5 |
S4—Sn4—S5 | 91.64 (5) | H18A—C18—H18C | 109.5 |
S6—Sn4—S5 | 99.58 (5) | H18B—C18—H18C | 109.5 |
C28—Sn4—N4 | 73.6 (2) | C20—C19—C24 | 118.8 (5) |
S4—Sn4—N4 | 85.24 (12) | C20—C19—Sn3 | 117.1 (4) |
S6—Sn4—N4 | 85.15 (12) | C24—C19—Sn3 | 124.1 (4) |
S5—Sn4—N4 | 175.26 (12) | C21—C20—C19 | 119.9 (6) |
C19—Sn3—S5 | 119.64 (15) | C21—C20—C25 | 121.3 (6) |
C19—Sn3—S3 | 104.01 (15) | C19—C20—C25 | 118.8 (5) |
S5—Sn3—S3 | 132.02 (6) | C22—C21—C20 | 120.9 (6) |
C19—Sn3—S4 | 105.44 (16) | C22—C21—H21 | 119.6 |
S5—Sn3—S4 | 91.07 (5) | C20—C21—H21 | 119.6 |
S3—Sn3—S4 | 95.92 (6) | C23—C22—C21 | 119.4 (6) |
C19—Sn3—N3 | 74.23 (19) | C23—C22—H22 | 120.3 |
S5—Sn3—N3 | 86.46 (12) | C21—C22—H22 | 120.3 |
S3—Sn3—N3 | 87.17 (12) | C22—C23—C24 | 120.4 (6) |
S4—Sn3—N3 | 176.87 (12) | C22—C23—H23 | 119.8 |
C7—N1—C9 | 111.8 (5) | C24—C23—H23 | 119.8 |
C7—N1—C8 | 109.2 (5) | C23—C24—C19 | 120.5 (6) |
C9—N1—C8 | 108.9 (5) | C23—C24—H24 | 119.7 |
C7—N1—Sn1 | 100.8 (3) | C19—C24—H24 | 119.7 |
C9—N1—Sn1 | 114.8 (4) | N3—C25—C20 | 110.8 (5) |
C8—N1—Sn1 | 111.1 (4) | N3—C25—H25A | 109.5 |
C18—N2—C16 | 111.8 (5) | C20—C25—H25A | 109.5 |
C18—N2—C17 | 109.3 (5) | N3—C25—H25B | 109.5 |
C16—N2—C17 | 109.5 (5) | C20—C25—H25B | 109.5 |
C18—N2—Sn2 | 115.2 (4) | H25A—C25—H25B | 108.1 |
C16—N2—Sn2 | 100.9 (3) | N3—C26—H26A | 109.5 |
C17—N2—Sn2 | 109.9 (4) | N3—C26—H26B | 109.5 |
C26—N3—C27 | 109.5 (5) | H26A—C26—H26B | 109.5 |
C26—N3—C25 | 110.8 (5) | N3—C26—H26C | 109.5 |
C27—N3—C25 | 110.1 (5) | H26A—C26—H26C | 109.5 |
C26—N3—Sn3 | 115.7 (4) | H26B—C26—H26C | 109.5 |
C27—N3—Sn3 | 110.9 (3) | N3—C27—H27A | 109.5 |
C25—N3—Sn3 | 99.4 (3) | N3—C27—H27B | 109.5 |
C34—N4—C35 | 110.5 (5) | H27A—C27—H27B | 109.5 |
C34—N4—C36 | 111.8 (5) | N3—C27—H27C | 109.5 |
C35—N4—C36 | 109.1 (5) | H27A—C27—H27C | 109.5 |
C34—N4—Sn4 | 99.7 (4) | H27B—C27—H27C | 109.5 |
C35—N4—Sn4 | 111.8 (4) | C33—C28—C29 | 120.3 (6) |
C36—N4—Sn4 | 113.8 (4) | C33—C28—Sn4 | 123.2 (5) |
Sn2—S1—Sn1 | 88.57 (5) | C29—C28—Sn4 | 116.5 (5) |
Sn1—S2—Sn2 | 88.73 (5) | C30—C29—C28 | 118.5 (7) |
Sn2—S3—Sn3 | 109.04 (6) | C30—C29—C34 | 122.1 (6) |
Sn4—S4—Sn3 | 88.53 (5) | C28—C29—C34 | 119.4 (5) |
Sn3—S5—Sn4 | 88.42 (5) | C31—C30—C29 | 121.6 (8) |
Sn1—S6—Sn4 | 108.29 (5) | C31—C30—H30 | 119.2 |
C2—C1—C6 | 119.6 (6) | C29—C30—H30 | 119.2 |
C2—C1—Sn1 | 116.7 (4) | C30—C31—C32 | 121.2 (8) |
C6—C1—Sn1 | 123.7 (5) | C30—C31—H31 | 119.4 |
C1—C2—C3 | 119.7 (6) | C32—C31—H31 | 119.4 |
C1—C2—C7 | 119.7 (5) | C31—C32—C33 | 118.4 (8) |
C3—C2—C7 | 120.6 (6) | C31—C32—H32 | 120.8 |
C4—C3—C2 | 120.2 (8) | C33—C32—H32 | 120.8 |
C4—C3—H3 | 119.9 | C28—C33—C32 | 120.0 (7) |
C2—C3—H3 | 119.9 | C28—C33—H33 | 120.0 |
C3—C4—C5 | 122.1 (8) | C32—C33—H33 | 120.0 |
C3—C4—H4 | 118.9 | N4—C34—C29 | 110.2 (5) |
C5—C4—H4 | 118.9 | N4—C34—H34A | 109.6 |
C4—C5—C6 | 118.8 (8) | C29—C34—H34A | 109.6 |
C4—C5—H5 | 120.6 | N4—C34—H34B | 109.6 |
C6—C5—H5 | 120.6 | C29—C34—H34B | 109.6 |
C1—C6—C5 | 119.6 (7) | H34A—C34—H34B | 108.1 |
C1—C6—H6 | 120.2 | N4—C35—H35A | 109.5 |
C5—C6—H6 | 120.2 | N4—C35—H35B | 109.5 |
N1—C7—C2 | 110.1 (5) | H35A—C35—H35B | 109.5 |
N1—C7—H7A | 109.6 | N4—C35—H35C | 109.5 |
C2—C7—H7A | 109.6 | H35A—C35—H35C | 109.5 |
N1—C7—H7B | 109.6 | H35B—C35—H35C | 109.5 |
C2—C7—H7B | 109.6 | N4—C36—H36A | 109.5 |
H7A—C7—H7B | 108.1 | N4—C36—H36B | 109.5 |
N1—C8—H8A | 109.5 | H36A—C36—H36B | 109.5 |
N1—C8—H8B | 109.5 | N4—C36—H36C | 109.5 |
H8A—C8—H8B | 109.5 | H36A—C36—H36C | 109.5 |
N1—C8—H8C | 109.5 | H36B—C36—H36C | 109.5 |
H8A—C8—H8C | 109.5 | Cl2A—C37—Cl3B | 95.2 (8) |
H8B—C8—H8C | 109.5 | Cl2A—C37—Cl3A | 110.9 (5) |
N1—C9—H9A | 109.5 | Cl2A—C37—Cl1B | 114.2 (7) |
N1—C9—H9B | 109.5 | Cl3B—C37—Cl1B | 110.0 (5) |
H9A—C9—H9B | 109.5 | Cl3A—C37—Cl1B | 102.1 (5) |
N1—C9—H9C | 109.5 | Cl2A—C37—Cl1A | 111.1 (5) |
H9A—C9—H9C | 109.5 | Cl3B—C37—Cl1A | 117.8 (7) |
H9B—C9—H9C | 109.5 | Cl3A—C37—Cl1A | 109.9 (5) |
C15—C10—C11 | 119.9 (5) | Cl3B—C37—Cl2B | 109.2 (5) |
C15—C10—Sn2 | 123.9 (4) | Cl3A—C37—Cl2B | 124.8 (7) |
C11—C10—Sn2 | 116.2 (4) | Cl1B—C37—Cl2B | 110.2 (4) |
C12—C11—C10 | 119.3 (6) | Cl1A—C37—Cl2B | 105.4 (6) |
C12—C11—C16 | 121.2 (6) | Cl2A—C37—H37 | 108.3 |
C10—C11—C16 | 119.5 (5) | Cl3B—C37—H37 | 115.1 |
C13—C12—C11 | 120.2 (6) | Cl3A—C37—H37 | 108.3 |
C13—C12—H12 | 119.9 | Cl1B—C37—H37 | 112.8 |
C11—C12—H12 | 119.9 | Cl1A—C37—H37 | 108.3 |
C14—C13—C12 | 120.5 (6) | Cl2B—C37—H37 | 98.9 |
C1—Sn1—N1—C7 | −34.1 (4) | C6—C1—C2—C3 | −1.1 (9) |
S2—Sn1—N1—C7 | −160.1 (4) | Sn1—C1—C2—C3 | −179.9 (5) |
S6—Sn1—N1—C7 | 69.6 (3) | C6—C1—C2—C7 | −179.1 (6) |
C1—Sn1—N1—C9 | −154.3 (5) | Sn1—C1—C2—C7 | 2.1 (7) |
S2—Sn1—N1—C9 | 79.7 (4) | C1—C2—C3—C4 | 1.9 (10) |
S6—Sn1—N1—C9 | −50.7 (4) | C7—C2—C3—C4 | 180.0 (7) |
C1—Sn1—N1—C8 | 81.5 (4) | C2—C3—C4—C5 | −1.9 (13) |
S2—Sn1—N1—C8 | −44.5 (4) | C3—C4—C5—C6 | 1.1 (13) |
S6—Sn1—N1—C8 | −174.9 (4) | C2—C1—C6—C5 | 0.2 (9) |
C10—Sn2—N2—C18 | −155.1 (5) | Sn1—C1—C6—C5 | 178.9 (5) |
S1—Sn2—N2—C18 | 77.0 (5) | C4—C5—C6—C1 | −0.2 (11) |
S3—Sn2—N2—C18 | −49.3 (5) | C9—N1—C7—C2 | 166.9 (5) |
C10—Sn2—N2—C16 | −34.5 (4) | C8—N1—C7—C2 | −72.5 (6) |
S1—Sn2—N2—C16 | −162.4 (4) | Sn1—N1—C7—C2 | 44.5 (5) |
S3—Sn2—N2—C16 | 71.2 (3) | C1—C2—C7—N1 | −36.9 (8) |
C10—Sn2—N2—C17 | 81.0 (4) | C3—C2—C7—N1 | 145.0 (6) |
S1—Sn2—N2—C17 | −46.9 (4) | S1—Sn2—C10—C15 | −87.2 (5) |
S3—Sn2—N2—C17 | −173.3 (4) | S3—Sn2—C10—C15 | 114.8 (4) |
C19—Sn3—N3—C26 | −153.5 (5) | S2—Sn2—C10—C15 | 12.3 (5) |
S5—Sn3—N3—C26 | 84.4 (4) | N2—Sn2—C10—C15 | −161.8 (5) |
S3—Sn3—N3—C26 | −48.1 (4) | S1—Sn2—C10—C11 | 94.3 (4) |
C19—Sn3—N3—C27 | 81.0 (4) | S3—Sn2—C10—C11 | −63.7 (4) |
S5—Sn3—N3—C27 | −41.2 (4) | S2—Sn2—C10—C11 | −166.2 (4) |
S3—Sn3—N3—C27 | −173.6 (4) | N2—Sn2—C10—C11 | 19.7 (4) |
C19—Sn3—N3—C25 | −34.9 (4) | C15—C10—C11—C12 | 0.1 (9) |
S5—Sn3—N3—C25 | −157.1 (3) | Sn2—C10—C11—C12 | 178.6 (4) |
S3—Sn3—N3—C25 | 70.5 (3) | C15—C10—C11—C16 | −179.5 (5) |
C28—Sn4—N4—C34 | −35.5 (4) | Sn2—C10—C11—C16 | −1.0 (7) |
S4—Sn4—N4—C34 | −161.6 (4) | C10—C11—C12—C13 | −0.8 (9) |
S6—Sn4—N4—C34 | 71.0 (4) | C16—C11—C12—C13 | 178.8 (6) |
C28—Sn4—N4—C35 | 81.2 (5) | C11—C12—C13—C14 | 1.4 (10) |
S4—Sn4—N4—C35 | −44.9 (4) | C12—C13—C14—C15 | −1.3 (10) |
S6—Sn4—N4—C35 | −172.3 (4) | C13—C14—C15—C10 | 0.6 (9) |
C28—Sn4—N4—C36 | −154.7 (5) | C11—C10—C15—C14 | 0.0 (8) |
S4—Sn4—N4—C36 | 79.2 (4) | Sn2—C10—C15—C14 | −178.4 (4) |
S6—Sn4—N4—C36 | −48.2 (4) | C18—N2—C16—C11 | 166.6 (5) |
C10—Sn2—S1—Sn1 | 108.61 (18) | C17—N2—C16—C11 | −72.2 (6) |
S3—Sn2—S1—Sn1 | −98.08 (7) | Sn2—N2—C16—C11 | 43.6 (5) |
S2—Sn2—S1—Sn1 | 3.71 (6) | C12—C11—C16—N2 | 146.3 (6) |
N2—Sn2—S1—Sn1 | 176.82 (12) | C10—C11—C16—N2 | −34.1 (8) |
C1—Sn1—S1—Sn2 | −128.22 (16) | S5—Sn3—C19—C20 | 96.0 (4) |
S2—Sn1—S1—Sn2 | −3.88 (6) | S3—Sn3—C19—C20 | −63.3 (5) |
S6—Sn1—S1—Sn2 | 126.66 (5) | S4—Sn3—C19—C20 | −163.7 (4) |
C1—Sn1—S2—Sn2 | 113.3 (2) | N3—Sn3—C19—C20 | 19.6 (4) |
S6—Sn1—S2—Sn2 | −99.21 (7) | S5—Sn3—C19—C24 | −84.3 (5) |
S1—Sn1—S2—Sn2 | 3.73 (6) | S3—Sn3—C19—C24 | 116.3 (5) |
N1—Sn1—S2—Sn2 | −179.89 (12) | S4—Sn3—C19—C24 | 16.0 (5) |
C10—Sn2—S2—Sn1 | −130.11 (15) | N3—Sn3—C19—C24 | −160.8 (5) |
S1—Sn2—S2—Sn1 | −3.87 (6) | C24—C19—C20—C21 | −0.3 (9) |
S3—Sn2—S2—Sn1 | 122.99 (5) | Sn3—C19—C20—C21 | 179.4 (5) |
C10—Sn2—S3—Sn3 | −153.56 (16) | C24—C19—C20—C25 | −179.7 (5) |
S1—Sn2—S3—Sn3 | 48.74 (9) | Sn3—C19—C20—C25 | −0.1 (7) |
S2—Sn2—S3—Sn3 | −49.11 (7) | C19—C20—C21—C22 | 0.2 (10) |
N2—Sn2—S3—Sn3 | 133.43 (13) | C25—C20—C21—C22 | 179.6 (6) |
C19—Sn3—S3—Sn2 | −176.05 (17) | C20—C21—C22—C23 | 0.5 (11) |
S5—Sn3—S3—Sn2 | 28.32 (10) | C21—C22—C23—C24 | −1.0 (11) |
S4—Sn3—S3—Sn2 | −68.48 (7) | C22—C23—C24—C19 | 0.9 (10) |
N3—Sn3—S3—Sn2 | 110.98 (12) | C20—C19—C24—C23 | −0.2 (9) |
C28—Sn4—S4—Sn3 | 113.7 (2) | Sn3—C19—C24—C23 | −179.9 (4) |
S6—Sn4—S4—Sn3 | −98.85 (6) | C26—N3—C25—C20 | 166.8 (5) |
S5—Sn4—S4—Sn3 | 4.37 (6) | C27—N3—C25—C20 | −71.8 (6) |
N4—Sn4—S4—Sn3 | −179.21 (13) | Sn3—N3—C25—C20 | 44.6 (5) |
C19—Sn3—S4—Sn4 | −125.75 (16) | C21—C20—C25—N3 | 144.4 (6) |
S5—Sn3—S4—Sn4 | −4.53 (6) | C19—C20—C25—N3 | −36.2 (8) |
S3—Sn3—S4—Sn4 | 127.93 (6) | S4—Sn4—C28—C33 | −88.6 (5) |
C19—Sn3—S5—Sn4 | 112.83 (18) | S6—Sn4—C28—C33 | 117.8 (5) |
S3—Sn3—S5—Sn4 | −94.60 (7) | S5—Sn4—C28—C33 | 13.5 (5) |
S4—Sn3—S5—Sn4 | 4.35 (6) | N4—Sn4—C28—C33 | −161.7 (5) |
N3—Sn3—S5—Sn4 | −177.57 (12) | S4—Sn4—C28—C29 | 91.8 (4) |
C28—Sn4—S5—Sn3 | −129.13 (16) | S6—Sn4—C28—C29 | −61.8 (4) |
S4—Sn4—S5—Sn3 | −4.54 (6) | S5—Sn4—C28—C29 | −166.1 (4) |
S6—Sn4—S5—Sn3 | 123.04 (5) | N4—Sn4—C28—C29 | 18.7 (4) |
C1—Sn1—S6—Sn4 | −175.42 (17) | C33—C28—C29—C30 | 0.6 (9) |
S2—Sn1—S6—Sn4 | 32.20 (10) | Sn4—C28—C29—C30 | −179.7 (5) |
S1—Sn1—S6—Sn4 | −67.25 (7) | C33—C28—C29—C34 | −178.1 (6) |
N1—Sn1—S6—Sn4 | 112.33 (12) | Sn4—C28—C29—C34 | 1.5 (7) |
C28—Sn4—S6—Sn1 | −162.15 (17) | C28—C29—C30—C31 | −2.0 (11) |
S4—Sn4—S6—Sn1 | 45.73 (9) | C34—C29—C30—C31 | 176.7 (7) |
S5—Sn4—S6—Sn1 | −53.57 (7) | C29—C30—C31—C32 | 2.1 (13) |
N4—Sn4—S6—Sn1 | 126.13 (14) | C30—C31—C32—C33 | −0.8 (13) |
S2—Sn1—C1—C2 | 90.6 (4) | C29—C28—C33—C32 | 0.6 (9) |
S6—Sn1—C1—C2 | −64.4 (4) | Sn4—C28—C33—C32 | −179.0 (5) |
S1—Sn1—C1—C2 | −167.4 (4) | C31—C32—C33—C28 | −0.5 (11) |
N1—Sn1—C1—C2 | 17.9 (4) | C35—N4—C34—C29 | −71.9 (6) |
S2—Sn1—C1—C6 | −88.2 (5) | C36—N4—C34—C29 | 166.5 (5) |
S6—Sn1—C1—C6 | 116.8 (5) | Sn4—N4—C34—C29 | 45.8 (5) |
S1—Sn1—C1—C6 | 13.9 (5) | C30—C29—C34—N4 | 143.1 (6) |
N1—Sn1—C1—C6 | −160.9 (5) | C28—C29—C34—N4 | −38.2 (8) |
Experimental details
Crystal data | |
Chemical formula | [Sn4(C9H12N)4S6]·CHCl3 |
Mr | 1323.27 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 297 |
a, b, c (Å) | 18.3436 (16), 12.9426 (11), 20.5064 (17) |
β (°) | 95.957 (2) |
V (Å3) | 4842.2 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.50 |
Crystal size (mm) | 0.22 × 0.20 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SMART; Bruker, 2000) |
Tmin, Tmax | 0.592, 0.685 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 45895, 8532, 7847 |
Rint | 0.048 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.085, 1.25 |
No. of reflections | 8532 |
No. of parameters | 523 |
No. of restraints | 36 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.0212P)2 + 10.3311P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.65, −0.64 |
Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2000), SHELXTL (Bruker, 2001), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2007).
Y—X···Cg | X—H | H···Cg | X···Cg | X—H···Cg |
C30—H30···Cg1i | 0.93 | 3.23 | 3.98 (1) | 139 |
C37—H37···Cg2ii | 0.98 | 2.87 | 3.61 (1) | 133 |
Symmetry codes: (i) 1-x, -1/2+y, 1/2-z, (ii) 1-x, 1-y, 1-z |
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 N→Sn 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 N→Sn 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 N→Sn 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.