metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

Tetra­kis(2,3,5,6-tetra­fluoro­benzene­thiol­ato-κS)(tri­phenyl­phosphane-κP)osmium(IV): a monoclinic polymorph

aCentro de Química del Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, Ciudad Universitaria, 72570 Puebla, Pue., Mexico, bFacultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Ciudad Universitaria, 72570 Puebla, Pue., Mexico, and cInstituto de Física, Benemérita Universidad Autónoma de Puebla, Av. San Claudio y 18 Sur, 72570 Puebla, Pue., Mexico
*Correspondence e-mail: sylvain_bernes@hotmail.com

Edited by M. Zeller, Purdue University, USA (Received 7 October 2019; accepted 2 December 2019; online 6 December 2019)

The structure of the title compound, [Os(C6HF4S)4{P(C6H5)3}], has been previously reported [Arroyo et al. (1994[Arroyo, M., Chamizo, J. A., Hughes, D. L., Richards, R. L., Roman, P., Sosa, P. & Torrens, H. (1994). J. Chem. Soc. Dalton Trans. pp. 1819-1824.]). J. Chem. Soc. Dalton Trans. pp. 1819–1824], in the space group P[\overline{1}]. We have now obtained a monoclinic polymorph for this compound, crystallized from ethanol, while the previous form was obtained from a hexa­ne/chloro­form mixture. The mol­ecular structure is based on a trigonal–bipyramidal OsIV coordination geometry, close to that observed previously in the triclinic form.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Within the chemistry of OsIV complexes bearing polyfluorinated thiol­ate ligands with general formula [Os(thiol­ate)4(phosphine)] (Arroyo et al., 1994[Arroyo, M., Chamizo, J. A., Hughes, D. L., Richards, R. L., Roman, P., Sosa, P. & Torrens, H. (1994). J. Chem. Soc. Dalton Trans. pp. 1819-1824.], 2009[Arroyo, M., Mendoza, C., Bernès, S., Torrens, H. & Morales-Rojas, H. (2009). Polyhedron, 28, 2625-2634.]; Mendoza et al., 2006[Mendoza, C., Bernès, S. & Arroyo, M. (2006). Acta Cryst. C62, m201-m204.]; Cerón et al., 2006[Cerón, M., Arroyo, M. & Bernès, S. (2006). Acta Cryst. E62, m2167-m2169.]), we are currently inter­ested in substitution reactions, allowing complexes to be prepared in which the thiol­ate ligand in an axial position is replaced by a halogen or a pseudo-halogen, such as an azide. During the recrystallization of a batch of the starting material [Os(SC6F4H)4(PPh3)] from an ethano­lic solution, brown crystals were obtained in space group P21/c, while this compound was previously reported in space group P[\overline{1}] (Arroyo et al., 1994[Arroyo, M., Chamizo, J. A., Hughes, D. L., Richards, R. L., Roman, P., Sosa, P. & Torrens, H. (1994). J. Chem. Soc. Dalton Trans. pp. 1819-1824.]). Simulated powder-diffraction patterns for both forms are clearly different, confirming that triclinic and monoclinic crystals are polymorphs. We assume that the polymorphism is triggered by the solvent used for crystallization, ethanol for the monoclinic form, and a hexa­ne:chloro­form mixture for the triclinic form. Moreover, a third form for the same compound has been reported, in which the complex crystallized as a n-hexane hemisolvate (Cerón et al., 2006[Cerón, M., Arroyo, M. & Bernès, S. (2006). Acta Cryst. E62, m2167-m2169.]).

The title polymorph (Fig. 1[link]) has the expected trigonal–bipyramidal coordination geometry, with the phosphine and one thiol­ate ligand in axial positions, with bond lengths Os—P = 2.4178 (19) and Os—Sax = 2.421 (2) Å, while the equatorial positions are occupied by three thiol­ate ligands, with shorter bond lengths Os—Seq = 2.207 (2)–2.225 (2) Å. A fit between the mol­ecular geometries of the two polymorphs gives an r.m.s deviation limited to 0.179 Å (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]). The single conformer found in these two polymorphs contrasts with that found in the [Os(C6HF4S)4(PPh3)]·n-hexane hemisolvate (Cerón et al., 2006[Cerón, M., Arroyo, M. & Bernès, S. (2006). Acta Cryst. E62, m2167-m2169.]): the fit between the mol­ecular geometry of the P21/c unsolvated complex and the n-hexane hemisolvate gives an r.m.s deviation of 1.016 Å.

[Figure 1]
Figure 1
Mol­ecular structure of the title compound, with displacement ellipsoids at the 30% probability level. F atoms are labelled F1 to F16 starting from the F site bonded to C20, and H atoms are omitted for clarity.

The shortest inter­molecular contact in the crystal structure is a ππ contact between two benzene rings of neighbouring mol­ecules, with a large separation of 4.047 (5) Å. In the case of the triclinic polymorph, inter­molecular ππ contacts were more efficient, with a separation between stacked rings of 3.744 Å (Arroyo et al., 1994[Arroyo, M., Chamizo, J. A., Hughes, D. L., Richards, R. L., Roman, P., Sosa, P. & Torrens, H. (1994). J. Chem. Soc. Dalton Trans. pp. 1819-1824.]). However, this difference is probably not significant, since both polymorphs display almost the same density at room temperature. As expected, the complex crystallized with n-hexane in the lattice has a lower density (1.777 g cm−3 versus 1.832 g cm−3 for the unsolvated crystal), as well as larger separations between stacked benzene rings of 4.529 Å (Cerón et al., 2006[Cerón, M., Arroyo, M. & Bernès, S. (2006). Acta Cryst. E62, m2167-m2169.]).

Synthesis and crystallization

The synthesis of the title complex was carried out using an methodology similar to that described for the triclinic polymorph (Arroyo et al., 1994[Arroyo, M., Chamizo, J. A., Hughes, D. L., Richards, R. L., Roman, P., Sosa, P. & Torrens, H. (1994). J. Chem. Soc. Dalton Trans. pp. 1819-1824.]), by reacting 2,3,5,6-tetra­fluoro­benzene­thiol (0.6 ml, 4 mmol), OsO4 (0.25 g, 1 mmol) and PPh3 (0.773 g, 3 mmol) in ethanol (15 ml) under stirring for two days at 295 K. During that time, a dark-green precipitate appeared; the solvent was distilled off under reduced pressure and the precipitate was filtered off and washed with cold ethanol (10 ml). The washed precipitate was dissolved again in ethanol and brown crystals of the title compound were obtained by slow evaporation, in 90% yield.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1[link]. Because of an unresolved disorder affecting the benzene ring of thiol S1 (axial position), the C19–C24 ring was restrained to have a geometry similar to that of the C31–C36 ring, within standard deviations of 0.02 Å (1,2-distances) and 0.04 Å (1,3-distances; Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]).

Table 1
Experimental details

Crystal data
Chemical formula [Os(C6HF4S)4(C18H15P)]
Mr 1176.98
Crystal system, space group Monoclinic, P21/c
Temperature (K) 295
a, b, c (Å) 12.4008 (5), 13.8892 (7), 25.2321 (11)
β (°) 100.991 (3)
V3) 4266.2 (3)
Z 4
Radiation type Ag Kα, λ = 0.56083 Å
μ (mm−1) 1.80
Crystal size (mm) 0.20 × 0.06 × 0.03
 
Data collection
Diffractometer Stoe Stadivari
Absorption correction Multi-scan (X-AREA; Stoe & Cie, 2018[Stoe & Cie (2018). X-AREA and X-RED32, Stoe & Cie, Darmstadt, Germany.])
Tmin, Tmax 0.388, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 93107, 8692, 4264
Rint 0.186
(sin θ/λ)max−1) 0.625
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.092, 0.80
No. of reflections 8692
No. of parameters 577
No. of restraints 12
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.71, −1.05
Computer programs: X-AREA (Stoe & Cie, 2018[Stoe & Cie (2018). X-AREA and X-RED32, Stoe & Cie, Darmstadt, Germany.]), SHELXT2018 (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2018 (Sheldrick, 2018), XP in SHELXTL-Plus (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]), publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data


Computing details top

Data collection: X-AREA (Stoe & Cie, 2018); cell refinement: X-AREA (Stoe & Cie, 2018); data reduction: X-AREA (Stoe & Cie, 2018); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2018); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Tetrakis(2,3,5,6-tetrafluorobenzenethiolato-κS)(triphenylphosphane-κP)osmium(IV) top
Crystal data top
[Os(C6HF4S)4(C18H15P)]F(000) = 2280
Mr = 1176.98Dx = 1.832 Mg m3
Monoclinic, P21/cAg Kα radiation, λ = 0.56083 Å
a = 12.4008 (5) ÅCell parameters from 22104 reflections
b = 13.8892 (7) Åθ = 2.0–23.5°
c = 25.2321 (11) ŵ = 1.80 mm1
β = 100.991 (3)°T = 295 K
V = 4266.2 (3) Å3Plate, brown
Z = 40.20 × 0.06 × 0.03 mm
Data collection top
Stoe Stadivari
diffractometer
8692 independent reflections
Radiation source: Sealed X-ray tube, Axo Astix-f Microfocus source4264 reflections with I > 2σ(I)
Graded multilayer mirror monochromatorRint = 0.186
Detector resolution: 5.81 pixels mm-1θmax = 20.5°, θmin = 2.0°
ω scansh = 1515
Absorption correction: multi-scan
(X-AREA; Stoe & Cie, 2018)
k = 1717
Tmin = 0.388, Tmax = 1.000l = 3131
93107 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 0.80 w = 1/[σ2(Fo2) + (0.0305P)2]
where P = (Fo2 + 2Fc2)/3
8692 reflections(Δ/σ)max = 0.002
577 parametersΔρmax = 0.71 e Å3
12 restraintsΔρmin = 1.05 e Å3
0 constraints
Special details top

Refinement. All H atoms were placed in idealized positions, with C—H bond lengths of 0.93 Å and Uiso(H) = 1.2×Ueq(carrier C atom).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Os10.26257 (2)0.72225 (2)0.54794 (2)0.05251 (10)
P10.23237 (15)0.63058 (14)0.46496 (8)0.0522 (5)
S10.30213 (16)0.82548 (15)0.62659 (8)0.0668 (6)
S20.38093 (16)0.60874 (16)0.58113 (8)0.0670 (6)
S30.08383 (15)0.70369 (16)0.54370 (8)0.0656 (6)
S40.32211 (17)0.83611 (16)0.49853 (8)0.0695 (6)
C10.2366 (5)0.5002 (5)0.4732 (3)0.0554 (19)
C20.2910 (6)0.4419 (6)0.4430 (3)0.065 (2)
H20.3292750.4695880.4185690.077*
C30.2900 (7)0.3425 (6)0.4483 (4)0.074 (2)
H30.3263740.3040470.4270950.089*
C40.2349 (6)0.3008 (6)0.4851 (3)0.067 (2)
H40.2342900.2342730.4891470.080*
C50.1808 (6)0.3593 (7)0.5158 (3)0.067 (2)
H50.1425170.3316980.5402150.081*
C60.1826 (6)0.4577 (6)0.5106 (3)0.059 (2)
H60.1475680.4961650.5323080.071*
C70.3332 (5)0.6512 (5)0.4226 (3)0.0505 (18)
C80.3022 (6)0.6737 (6)0.3679 (3)0.071 (2)
H80.2286020.6853110.3535080.085*
C90.3789 (7)0.6791 (6)0.3349 (3)0.079 (3)
H90.3559140.6908680.2981490.095*
C100.4878 (7)0.6673 (6)0.3555 (4)0.068 (2)
H100.5391750.6719260.3331650.081*
C110.5213 (6)0.6485 (5)0.4097 (3)0.062 (2)
H110.5956670.6409580.4239530.075*
C120.4450 (6)0.6406 (5)0.4432 (3)0.060 (2)
H120.4688440.6281020.4797440.071*
C130.1013 (5)0.6534 (5)0.4210 (3)0.0491 (18)
C140.0643 (6)0.7474 (5)0.4116 (3)0.062 (2)
H140.1059320.7981610.4286770.074*
C150.0352 (7)0.7661 (7)0.3766 (3)0.076 (2)
H150.0582040.8293210.3696750.092*
C160.0999 (6)0.6912 (8)0.3522 (3)0.075 (3)
H160.1668950.7035850.3296450.090*
C170.0634 (6)0.5979 (7)0.3619 (3)0.071 (2)
H170.1054220.5472730.3448340.086*
C180.0359 (6)0.5783 (6)0.3969 (3)0.064 (2)
H180.0580570.5148700.4040970.077*
C190.2201 (6)0.8136 (6)0.6755 (3)0.060 (2)
C200.1820 (8)0.8938 (9)0.6965 (4)0.094 (3)
C210.1238 (10)0.8909 (13)0.7386 (6)0.133 (6)
C220.0940 (10)0.8069 (16)0.7575 (5)0.155 (9)
H220.0475150.8043550.7823470.186*
C230.1340 (8)0.7267 (12)0.7392 (4)0.108 (4)
C240.1917 (6)0.7276 (9)0.6974 (3)0.081 (3)
C250.4434 (6)0.6181 (6)0.6500 (3)0.064 (2)
C260.5247 (7)0.6827 (7)0.6702 (3)0.073 (2)
C270.5792 (7)0.6786 (9)0.7224 (4)0.095 (3)
C280.5575 (10)0.6084 (12)0.7576 (4)0.117 (4)
H280.5965470.6048110.7928730.140*
C290.4772 (11)0.5456 (9)0.7386 (5)0.106 (3)
C300.4203 (8)0.5490 (8)0.6859 (4)0.082 (3)
C310.0172 (5)0.7771 (6)0.5852 (3)0.0599 (18)
C320.0365 (6)0.7385 (6)0.6231 (3)0.063 (2)
C330.1025 (7)0.7926 (8)0.6505 (4)0.079 (3)
C340.1176 (7)0.8872 (9)0.6387 (4)0.095 (3)
H340.1607570.9246620.6570370.114*
C350.0691 (7)0.9272 (7)0.6000 (5)0.089 (3)
C360.0021 (7)0.8743 (7)0.5736 (4)0.077 (3)
C370.3850 (6)0.9313 (5)0.5385 (3)0.061 (2)
C380.3314 (6)1.0133 (6)0.5508 (3)0.063 (2)
C390.3847 (7)1.0855 (6)0.5819 (4)0.069 (2)
C400.4944 (7)1.0825 (7)0.5998 (3)0.075 (2)
H400.5299851.1328600.6203280.091*
C410.5525 (7)1.0049 (7)0.5876 (4)0.072 (2)
C420.4977 (7)0.9318 (6)0.5572 (3)0.069 (2)
F10.2049 (5)0.9820 (5)0.6771 (3)0.129 (2)
F20.0878 (6)0.9748 (7)0.7556 (4)0.205 (4)
F30.1098 (5)0.6368 (7)0.7576 (3)0.166 (3)
F40.2212 (4)0.6441 (4)0.6780 (3)0.110 (2)
F50.5539 (4)0.7526 (4)0.6381 (2)0.0948 (17)
F60.6577 (4)0.7465 (6)0.7405 (2)0.142 (3)
F70.4529 (6)0.4739 (6)0.7704 (3)0.155 (3)
F80.3406 (4)0.4832 (4)0.6691 (2)0.0977 (16)
F90.0231 (4)0.6436 (4)0.6353 (2)0.0864 (14)
F100.1503 (4)0.7474 (5)0.6865 (2)0.118 (2)
F110.0839 (5)1.0212 (4)0.5886 (3)0.141 (2)
F120.0411 (4)0.9153 (4)0.5348 (2)0.1025 (18)
F130.2227 (4)1.0214 (3)0.5329 (2)0.0893 (15)
F140.3251 (4)1.1613 (3)0.5948 (2)0.0964 (16)
F150.6604 (4)0.9994 (4)0.6038 (2)0.1128 (19)
F160.5587 (4)0.8562 (3)0.5443 (2)0.0889 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Os10.04872 (15)0.06055 (18)0.04846 (16)0.00044 (17)0.00977 (11)0.00498 (19)
P10.0462 (10)0.0602 (13)0.0503 (13)0.0004 (9)0.0095 (10)0.0050 (10)
S10.0724 (13)0.0704 (14)0.0611 (13)0.0117 (10)0.0219 (11)0.0167 (11)
S20.0684 (13)0.0770 (16)0.0533 (12)0.0080 (10)0.0062 (10)0.0093 (11)
S30.0563 (11)0.0772 (17)0.0641 (13)0.0016 (10)0.0139 (10)0.0169 (11)
S40.0823 (14)0.0682 (15)0.0600 (13)0.0109 (11)0.0183 (11)0.0089 (11)
C10.044 (4)0.062 (5)0.058 (5)0.004 (3)0.003 (4)0.006 (4)
C20.066 (5)0.073 (6)0.059 (5)0.005 (4)0.023 (4)0.003 (5)
C30.083 (6)0.060 (6)0.082 (6)0.007 (5)0.023 (5)0.010 (5)
C40.059 (5)0.061 (6)0.075 (6)0.002 (4)0.001 (4)0.002 (5)
C50.065 (5)0.080 (7)0.058 (5)0.004 (4)0.015 (4)0.008 (5)
C60.061 (5)0.054 (5)0.063 (5)0.000 (4)0.011 (4)0.003 (4)
C70.043 (4)0.057 (5)0.052 (5)0.001 (3)0.009 (3)0.011 (4)
C80.049 (5)0.110 (7)0.052 (5)0.004 (4)0.008 (4)0.006 (5)
C90.059 (5)0.119 (8)0.062 (6)0.001 (5)0.019 (5)0.002 (5)
C100.068 (6)0.072 (6)0.071 (6)0.001 (4)0.034 (5)0.010 (5)
C110.050 (4)0.071 (6)0.070 (6)0.001 (4)0.022 (4)0.003 (5)
C120.054 (5)0.069 (6)0.056 (5)0.004 (4)0.011 (4)0.010 (4)
C130.046 (4)0.049 (5)0.053 (5)0.005 (3)0.011 (3)0.001 (4)
C140.055 (4)0.061 (7)0.063 (5)0.001 (3)0.005 (4)0.005 (4)
C150.073 (5)0.088 (7)0.067 (5)0.011 (5)0.009 (4)0.011 (5)
C160.048 (5)0.117 (9)0.058 (5)0.010 (5)0.005 (4)0.002 (5)
C170.052 (5)0.092 (7)0.066 (6)0.011 (4)0.001 (4)0.016 (5)
C180.048 (4)0.077 (6)0.065 (5)0.005 (4)0.007 (4)0.002 (4)
C190.046 (4)0.082 (7)0.055 (5)0.010 (4)0.013 (4)0.017 (4)
C200.081 (7)0.129 (10)0.072 (7)0.018 (7)0.013 (5)0.024 (7)
C210.080 (9)0.223 (19)0.100 (11)0.017 (9)0.027 (7)0.084 (12)
C220.053 (7)0.34 (3)0.068 (8)0.009 (11)0.008 (6)0.057 (13)
C230.065 (6)0.170 (12)0.088 (8)0.007 (8)0.009 (6)0.046 (9)
C240.060 (5)0.118 (9)0.069 (6)0.004 (6)0.023 (4)0.019 (7)
C250.061 (5)0.075 (6)0.055 (5)0.014 (4)0.012 (4)0.011 (5)
C260.056 (5)0.108 (8)0.053 (5)0.001 (5)0.007 (4)0.000 (5)
C270.063 (6)0.158 (11)0.060 (6)0.007 (6)0.003 (5)0.022 (7)
C280.107 (9)0.177 (14)0.057 (7)0.037 (9)0.007 (7)0.004 (8)
C290.125 (10)0.116 (11)0.077 (9)0.014 (7)0.023 (8)0.026 (8)
C300.084 (7)0.095 (8)0.067 (7)0.004 (6)0.009 (5)0.007 (6)
C310.058 (4)0.059 (5)0.060 (5)0.002 (4)0.004 (4)0.005 (5)
C320.061 (5)0.062 (6)0.067 (5)0.005 (4)0.015 (4)0.005 (4)
C330.067 (5)0.104 (8)0.071 (6)0.008 (6)0.024 (5)0.006 (6)
C340.073 (6)0.112 (10)0.102 (9)0.021 (6)0.021 (6)0.032 (7)
C350.071 (6)0.075 (8)0.120 (9)0.018 (5)0.014 (6)0.007 (7)
C360.057 (5)0.097 (8)0.074 (6)0.000 (5)0.008 (5)0.006 (6)
C370.072 (5)0.057 (5)0.056 (5)0.004 (4)0.017 (4)0.000 (4)
C380.057 (5)0.052 (5)0.075 (6)0.008 (4)0.006 (4)0.006 (4)
C390.070 (6)0.062 (6)0.077 (6)0.005 (4)0.016 (5)0.008 (5)
C400.076 (6)0.072 (7)0.073 (6)0.010 (5)0.001 (5)0.010 (5)
C410.054 (5)0.076 (7)0.082 (6)0.012 (5)0.004 (5)0.011 (5)
C420.083 (6)0.063 (6)0.068 (6)0.017 (5)0.029 (5)0.003 (5)
F10.131 (5)0.094 (5)0.157 (6)0.027 (4)0.018 (4)0.046 (5)
F20.158 (6)0.260 (10)0.207 (8)0.046 (6)0.061 (6)0.127 (8)
F30.117 (5)0.245 (10)0.144 (6)0.008 (5)0.042 (4)0.087 (6)
F40.095 (4)0.096 (5)0.148 (6)0.003 (3)0.043 (4)0.019 (4)
F50.076 (3)0.127 (5)0.084 (3)0.018 (3)0.024 (3)0.006 (3)
F60.088 (4)0.240 (8)0.089 (4)0.033 (4)0.007 (3)0.040 (5)
F70.203 (7)0.158 (7)0.101 (5)0.005 (5)0.018 (5)0.048 (5)
F80.112 (4)0.080 (4)0.100 (4)0.002 (3)0.016 (3)0.007 (3)
F90.087 (3)0.080 (4)0.096 (4)0.011 (3)0.030 (3)0.001 (3)
F100.094 (4)0.167 (6)0.105 (4)0.010 (3)0.054 (3)0.003 (4)
F110.135 (5)0.076 (4)0.200 (7)0.040 (4)0.005 (5)0.000 (4)
F120.087 (4)0.092 (4)0.132 (5)0.007 (3)0.028 (3)0.038 (4)
F130.065 (3)0.072 (3)0.126 (4)0.001 (2)0.008 (3)0.010 (3)
F140.093 (3)0.063 (3)0.133 (5)0.010 (3)0.022 (3)0.019 (3)
F150.054 (3)0.120 (5)0.153 (5)0.003 (3)0.008 (3)0.009 (4)
F160.079 (3)0.078 (4)0.116 (4)0.013 (2)0.034 (3)0.003 (3)
Geometric parameters (Å, º) top
Os1—S22.207 (2)C19—C201.358 (11)
Os1—S32.2138 (19)C19—C241.391 (11)
Os1—S42.225 (2)C20—F11.368 (11)
Os1—P12.4178 (19)C20—C211.394 (13)
Os1—S12.421 (2)C21—C221.339 (15)
P1—C131.812 (7)C21—F21.346 (15)
P1—C71.817 (7)C22—C231.336 (15)
P1—C11.822 (8)C22—H220.9300
S1—C191.749 (8)C23—C241.381 (11)
S2—C251.768 (8)C23—F31.386 (13)
S3—C311.773 (8)C24—F41.337 (11)
S4—C371.754 (8)C25—C261.373 (11)
C1—C21.373 (9)C25—C301.386 (12)
C1—C61.389 (10)C26—F51.358 (9)
C2—C31.388 (10)C26—C271.362 (12)
C2—H20.9300C27—F61.370 (11)
C3—C41.380 (10)C27—C281.379 (15)
C3—H30.9300C28—C291.341 (15)
C4—C51.382 (10)C28—H280.9300
C4—H40.9300C29—F71.350 (12)
C5—C61.374 (10)C29—C301.381 (13)
C5—H50.9300C30—F81.353 (10)
C6—H60.9300C31—C321.375 (9)
C7—C121.393 (9)C31—C361.393 (10)
C7—C81.394 (9)C32—F91.356 (8)
C8—C91.382 (10)C32—C331.388 (10)
C8—H80.9300C33—F101.332 (10)
C9—C101.362 (10)C33—C341.353 (11)
C9—H90.9300C34—C351.359 (12)
C10—C111.375 (10)C34—H340.9300
C10—H100.9300C35—F111.344 (10)
C11—C121.388 (9)C35—C361.374 (11)
C11—H110.9300C36—F121.329 (9)
C12—H120.9300C37—C381.383 (10)
C13—C141.389 (9)C37—C421.386 (10)
C13—C181.389 (9)C38—F131.342 (8)
C14—C151.398 (9)C38—C391.364 (10)
C14—H140.9300C39—C401.350 (10)
C15—C161.384 (11)C39—F141.361 (8)
C15—H150.9300C40—C411.364 (11)
C16—C171.378 (11)C40—H400.9300
C16—H160.9300C41—F151.324 (8)
C17—C181.399 (10)C41—C421.372 (11)
C17—H170.9300C42—F161.370 (8)
C18—H180.9300
S2—Os1—S3121.49 (8)C17—C18—H18120.0
S2—Os1—S4116.91 (8)C20—C19—C24114.5 (9)
S3—Os1—S4119.46 (8)C20—C19—S1119.4 (8)
S2—Os1—P186.24 (7)C24—C19—S1126.0 (6)
S3—Os1—P184.75 (7)C19—C20—F1118.9 (9)
S4—Os1—P184.39 (7)C19—C20—C21122.9 (12)
S2—Os1—S195.50 (7)F1—C20—C21118.1 (11)
S3—Os1—S198.80 (7)C22—C21—F2120.7 (15)
S4—Os1—S190.08 (7)C22—C21—C20120.9 (14)
P1—Os1—S1174.40 (7)F2—C21—C20117.9 (15)
C13—P1—C7104.5 (3)C23—C22—C21117.2 (14)
C13—P1—C1104.3 (3)C23—C22—H22121.4
C7—P1—C1102.4 (3)C21—C22—H22121.4
C13—P1—Os1114.2 (2)C22—C23—C24122.5 (13)
C7—P1—Os1114.6 (2)C22—C23—F3121.0 (13)
C1—P1—Os1115.4 (2)C24—C23—F3116.2 (13)
C19—S1—Os1117.9 (3)F4—C24—C23119.3 (11)
C25—S2—Os1117.1 (3)F4—C24—C19119.4 (7)
C31—S3—Os1118.6 (2)C23—C24—C19121.2 (11)
C37—S4—Os1111.8 (3)C26—C25—C30116.0 (8)
C2—C1—C6118.5 (8)C26—C25—S2124.5 (7)
C2—C1—P1122.0 (6)C30—C25—S2119.0 (7)
C6—C1—P1119.5 (6)F5—C26—C27117.8 (9)
C1—C2—C3121.3 (8)F5—C26—C25120.4 (7)
C1—C2—H2119.3C27—C26—C25121.7 (10)
C3—C2—H2119.3C26—C27—F6118.9 (11)
C4—C3—C2119.7 (8)C26—C27—C28122.0 (11)
C4—C3—H3120.1F6—C27—C28119.1 (10)
C2—C3—H3120.1C29—C28—C27116.9 (10)
C3—C4—C5119.1 (8)C29—C28—H28121.6
C3—C4—H4120.5C27—C28—H28121.6
C5—C4—H4120.5C28—C29—F7120.1 (12)
C6—C5—C4120.9 (8)C28—C29—C30122.1 (11)
C6—C5—H5119.6F7—C29—C30117.8 (13)
C4—C5—H5119.6F8—C30—C29119.3 (11)
C5—C6—C1120.4 (7)F8—C30—C25119.4 (8)
C5—C6—H6119.8C29—C30—C25121.3 (10)
C1—C6—H6119.8C32—C31—C36115.9 (7)
C12—C7—C8117.4 (7)C32—C31—S3121.9 (7)
C12—C7—P1120.8 (6)C36—C31—S3120.9 (6)
C8—C7—P1121.8 (5)F9—C32—C31118.8 (7)
C9—C8—C7121.2 (7)F9—C32—C33118.1 (8)
C9—C8—H8119.4C31—C32—C33123.1 (9)
C7—C8—H8119.4F10—C33—C34123.1 (9)
C10—C9—C8120.6 (8)F10—C33—C32117.8 (10)
C10—C9—H9119.7C34—C33—C32119.1 (9)
C8—C9—H9119.7C33—C34—C35119.5 (9)
C9—C10—C11119.5 (8)C33—C34—H34120.2
C9—C10—H10120.2C35—C34—H34120.2
C11—C10—H10120.2F11—C35—C34119.4 (10)
C10—C11—C12120.6 (7)F11—C35—C36119.1 (10)
C10—C11—H11119.7C34—C35—C36121.5 (10)
C12—C11—H11119.7F12—C36—C35119.6 (10)
C11—C12—C7120.7 (7)F12—C36—C31119.5 (8)
C11—C12—H12119.7C35—C36—C31120.8 (9)
C7—C12—H12119.7C38—C37—C42114.6 (7)
C14—C13—C18119.0 (7)C38—C37—S4124.7 (6)
C14—C13—P1119.9 (5)C42—C37—S4120.5 (6)
C18—C13—P1121.1 (6)F13—C38—C39118.5 (7)
C13—C14—C15120.4 (7)F13—C38—C37119.3 (7)
C13—C14—H14119.8C39—C38—C37122.2 (8)
C15—C14—H14119.8C40—C39—F14120.1 (8)
C16—C15—C14120.5 (8)C40—C39—C38121.1 (8)
C16—C15—H15119.7F14—C39—C38118.7 (8)
C14—C15—H15119.7C39—C40—C41119.4 (8)
C17—C16—C15119.0 (8)C39—C40—H40120.3
C17—C16—H16120.5C41—C40—H40120.3
C15—C16—H16120.5F15—C41—C40121.5 (8)
C16—C17—C18120.9 (8)F15—C41—C42119.5 (9)
C16—C17—H17119.5C40—C41—C42119.0 (8)
C18—C17—H17119.5F16—C42—C41117.6 (8)
C13—C18—C17120.1 (8)F16—C42—C37118.8 (8)
C13—C18—H18120.0C41—C42—C37123.6 (8)
C13—P1—C1—C297.8 (6)Os1—S2—C25—C30113.9 (7)
C7—P1—C1—C210.9 (7)C30—C25—C26—F5179.4 (7)
Os1—P1—C1—C2136.1 (5)S2—C25—C26—F57.7 (11)
C13—P1—C1—C681.6 (6)C30—C25—C26—C270.2 (13)
C7—P1—C1—C6169.7 (6)S2—C25—C26—C27171.6 (7)
Os1—P1—C1—C644.5 (6)F5—C26—C27—F62.2 (13)
C6—C1—C2—C31.9 (11)C25—C26—C27—F6178.5 (8)
P1—C1—C2—C3177.5 (6)F5—C26—C27—C28178.0 (9)
C1—C2—C3—C41.0 (12)C25—C26—C27—C281.3 (16)
C2—C3—C4—C50.6 (11)C26—C27—C28—C292.0 (18)
C3—C4—C5—C61.0 (11)F6—C27—C28—C29177.7 (10)
C4—C5—C6—C11.9 (11)C27—C28—C29—F7178.7 (10)
C2—C1—C6—C52.3 (10)C27—C28—C29—C301.4 (18)
P1—C1—C6—C5177.1 (5)C28—C29—C30—F8179.6 (10)
C13—P1—C7—C12179.8 (6)F7—C29—C30—F82.3 (15)
C1—P1—C7—C1271.7 (6)C28—C29—C30—C250.1 (17)
Os1—P1—C7—C1254.0 (6)F7—C29—C30—C25177.4 (9)
C13—P1—C7—C83.3 (7)C26—C25—C30—F8179.6 (7)
C1—P1—C7—C8105.2 (7)S2—C25—C30—F88.2 (11)
Os1—P1—C7—C8129.1 (6)C26—C25—C30—C290.7 (14)
C12—C7—C8—C94.1 (12)S2—C25—C30—C29171.5 (8)
P1—C7—C8—C9173.0 (6)Os1—S3—C31—C32119.9 (6)
C7—C8—C9—C103.4 (13)Os1—S3—C31—C3673.1 (6)
C8—C9—C10—C111.0 (13)C36—C31—C32—F9178.4 (6)
C9—C10—C11—C120.6 (12)S3—C31—C32—F910.9 (9)
C10—C11—C12—C70.2 (11)C36—C31—C32—C332.7 (11)
C8—C7—C12—C112.5 (10)S3—C31—C32—C33170.3 (6)
P1—C7—C12—C11174.5 (6)F9—C32—C33—F101.0 (11)
C7—P1—C13—C1481.0 (6)C31—C32—C33—F10179.8 (7)
C1—P1—C13—C14171.8 (6)F9—C32—C33—C34179.6 (7)
Os1—P1—C13—C1445.0 (6)C31—C32—C33—C341.6 (13)
C7—P1—C13—C1899.8 (6)F10—C33—C34—C35177.6 (8)
C1—P1—C13—C187.3 (7)C32—C33—C34—C350.9 (14)
Os1—P1—C13—C18134.2 (5)C33—C34—C35—F11179.8 (8)
C18—C13—C14—C152.6 (11)C33—C34—C35—C362.1 (15)
P1—C13—C14—C15178.2 (6)F11—C35—C36—F124.2 (13)
C13—C14—C15—C162.0 (12)C34—C35—C36—F12178.0 (8)
C14—C15—C16—C171.6 (12)F11—C35—C36—C31178.6 (7)
C15—C16—C17—C181.8 (12)C34—C35—C36—C310.8 (14)
C14—C13—C18—C172.8 (11)C32—C31—C36—F12175.7 (7)
P1—C13—C18—C17178.0 (6)S3—C31—C36—F128.0 (10)
C16—C17—C18—C132.4 (12)C32—C31—C36—C351.5 (11)
Os1—S1—C19—C20135.1 (6)S3—C31—C36—C35169.2 (7)
Os1—S1—C19—C2447.4 (8)Os1—S4—C37—C3891.8 (7)
C24—C19—C20—F1179.4 (8)Os1—S4—C37—C4293.2 (6)
S1—C19—C20—F12.9 (12)C42—C37—C38—F13177.7 (7)
C24—C19—C20—C213.1 (13)S4—C37—C38—F132.4 (11)
S1—C19—C20—C21174.7 (8)C42—C37—C38—C394.3 (12)
C19—C20—C21—C226 (2)S4—C37—C38—C39179.6 (6)
F1—C20—C21—C22176.6 (13)F13—C38—C39—C40178.2 (8)
C19—C20—C21—F2178.6 (9)C37—C38—C39—C403.8 (13)
F1—C20—C21—F23.8 (15)F13—C38—C39—F141.8 (12)
F2—C21—C22—C23179.3 (9)C37—C38—C39—F14176.2 (8)
C20—C21—C22—C238 (2)F14—C39—C40—C41178.5 (8)
C21—C22—C23—C248 (2)C38—C39—C40—C411.5 (14)
C21—C22—C23—F3178.3 (11)C39—C40—C41—F15179.2 (8)
C22—C23—C24—F4174.3 (10)C39—C40—C41—C420.1 (13)
F3—C23—C24—F40.6 (12)F15—C41—C42—F161.1 (12)
C22—C23—C24—C196.1 (15)C40—C41—C42—F16178.2 (8)
F3—C23—C24—C19179.7 (8)F15—C41—C42—C37180.0 (7)
C20—C19—C24—F4177.2 (7)C40—C41—C42—C370.8 (13)
S1—C19—C24—F45.2 (11)C38—C37—C42—F16176.1 (7)
C20—C19—C24—C233.1 (12)S4—C37—C42—F160.6 (10)
S1—C19—C24—C23174.5 (6)C38—C37—C42—C412.9 (12)
Os1—S2—C25—C2674.5 (7)S4—C37—C42—C41178.4 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···S20.932.983.742 (8)140
C14—H14···S40.932.963.725 (7)140
C14—H14···F11i0.932.553.223 (10)129
C18—H18···F9ii0.932.423.183 (10)139
C34—H34···F15iii0.932.583.140 (11)119
Symmetry codes: (i) x, y+2, z+1; (ii) x, y+1, z+1; (iii) x1, y, z.
 

Funding information

Funding for this research was provided by: Benemérita Universidad Autónoma de Puebla (grant 100003700-VIEP2019); Consejo Nacional de Ciencia y Tecnología (studentship No. 921296) (award No. 268178).

References

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