Redox, transmetalation, and stacking properties of tetrathiafulvalene-2,3,6,7-tetrathiolate bridged tin, nickel, and palladium compounds
Xie, Jiaze; Boyn, Jan-Niklas; Filatov, Alexander S.; McNeece, Andrew J.; Mazziotti, David A.; Anderson, John S.; Chemical Science 11 (2020) 1066–1078; doi:10.1039/C9SC04381K

data_1556878
_publ_section_title
;
 Redox, transmetalation, and stacking properties of
 tetrathiafulvalene-2,3,6,7-tetrathiolate bridged tin, nickel, and
 palladium compounds
;
_journal_issue                   4
_journal_name_full               'Chemical Science'
_journal_page_first              1066
_journal_page_last               1078
_journal_paper_doi               10.1039/C9SC04381K
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C25 H41.5 N0.5 O0.5 S8 Sn2, C32 H12 B F24'
_chemical_formula_sum            'C57 H53.5 B F24 N0.5 O0.5 S8 Sn2'
_chemical_formula_weight         1714.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-08-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-29 deposited with the CCDC.	2019-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.920(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5804(15)
_cell_length_b                   23.505(4)
_cell_length_c                   30.294(5)
_cell_measurement_reflns_used    9847
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.92
_cell_measurement_theta_min      2.33
_cell_volume                     6756.8(19)
_computing_cell_refinement       'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics
;
OLEX2: a complete structure solution, refinement and analysis program 
Dolomanov et al., 2009

Mercury: visualization and analysis of crystal structures
Macrae, et al., 2006

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann.
J. Appl. Cryst. (2009). 42, 339-341;

C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst. (2006). 39, 453-457.
;
_computing_publication_material
;
 APEX3 v.2015.5-2 (Bruker AXS Inc., 2015)
 OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'XL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'XT 2018/2 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            CMOS
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1444
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            103447
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        22.099
_diffrn_reflns_theta_max         22.098
_diffrn_reflns_theta_min         2.201
_diffrn_source                   'micro-focus X-ray tube'
_diffrn_source_type              'INCOATEC ImuS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.091
_exptl_absorpt_correction_T_max  0.7447
_exptl_absorpt_correction_T_min  0.4809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1542 before and 0.0947 after correction. 
The Ratio of minimum to maximum transmission is 0.6458.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_description       needle
_exptl_crystal_F_000             3408
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.959
_refine_diff_density_min         -0.943
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     850
_refine_ls_number_reflns         8304
_refine_ls_number_restraints     1098
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1244
_refine_ls_R_factor_gt           0.0820
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0634P)^2^+86.7726P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1755
_refine_ls_wR_factor_ref         0.1992
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5765
_reflns_number_total             8304
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc04381k2.cif
_cod_data_source_block           0751_jz
_cod_depositor_comments
;Adding full bibliography for 1556876--1556883.cif.

 Adding full bibliography for 1556876--1556883.cif.
;
_cod_original_cell_volume        6756.8(18)
_cod_original_formula_sum        'C57 H53.50 B F24 N0.50 O0.50 S8 Sn2'
_cod_database_code               1556878
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.780
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C57-C56
 1.45 with sigma of 0.02
 Sn1-N1
 2.67 with sigma of 0.02
 N1-C55A
 1.133 with sigma of 0.02
 C56A-C55A
 1.457 with sigma of 0.02
 C21-C20
 1.5 with sigma of 0.02
 C22-C21
 1.55 with sigma of 0.02
 C22A-C21A
 1.55 with sigma of 0.02
 F12A-C38A
 1.34 with sigma of 0.02
 F7A-C37A
 1.34 with sigma of 0.02
 F9-C37
 1.34 with sigma of 0.02
 F10-C38
 1.34 with sigma of 0.02
 F15A-C45
 1.34 with sigma of 0.02
 F4A-C29A
 1.34 with sigma of 0.02
 C8-C7
 1.45 with sigma of 0.02
 C9-C8
 1.45 with sigma of 0.02
 C9-C10
 1.55 with sigma of 0.02
 C9A-C8A = C10A-C10
 1.55 with sigma of 0.02
 O1-C55 \\sim O1-C58
 with sigma of 0.02
 C56-C55 \\sim C57-C58
 with sigma of 0.02
 Sn2-C19 \\sim Sn2-C19A
 with sigma of 0.02
 C19-C20 \\sim C19A-C20A
 with sigma of 0.02
 C20-C21 \\sim C20A-C21A
 with sigma of 0.02
 C21-C22 \\sim C21A-C22A
 with sigma of 0.02
 Sn2-C20 \\sim Sn2-C20A
 with sigma of 0.04
 C19-C21 \\sim C19A-C21A
 with sigma of 0.04
 C20-C22 \\sim C20A-C22A
 with sigma of 0.04
 C22-C21 \\sim C22A-C21A
 with sigma of 0.02
 C21A-C20A \\sim C21-C20
 with sigma of 0.02
 C20A-C19A \\sim C20-C19
 with sigma of 0.02
 Sn2-C19A \\sim Sn2-C19
 with sigma of 0.02
 C38A-C35A \\sim C37A-C33A \\sim C53-C49 \\sim C54-C51 \\sim C46-C43 \\sim
C45-C41 \\sim C30-C25 \\sim C29-
 C27
 with sigma of 0.02
 F7A-C37A \\sim F8A-C37A \\sim F9A-C37A \\sim F10A-C38A \\sim F12A-C38A \\sim
F11A-C38A \\sim F3-C30 ~
 F2-C30 \\sim F1-C30 \\sim F5-C29 \\sim F4-C29 \\sim F6-C29 \\sim F13-C45 \\sim
F15-C45 \\sim F14-C45 \\sim F18-
 C46 \\sim F17-C46 \\sim F16-C46
 with sigma of 0.02
 F10A-F11A \\sim F10A-F12A \\sim F11A-F12A
 with sigma of 0.02
 F7A-F8A \\sim F7A-F9A \\sim F8A-F9A
 with sigma of 0.02
 C31-C32 \\sim C33-C34 \\sim C35-C36
 with sigma of 0.02
 F10-C38 \\sim F12-C38 \\sim F11-C38 \\sim F9-C37 \\sim F8-C37 \\sim F7-C37
 with sigma of 0.02
 C38-C35 \\sim C38A-C35A \\sim C37-C33 \\sim C37A-C33A
 with sigma of 0.02
 C31A-C32A \\sim C33A-C34A \\sim C35A-C36A
 with sigma of 0.02
 F7-F8 \\sim F7-F9 \\sim F8-F9
 with sigma of 0.02
 F10-F11 \\sim F10-F12 \\sim F11-F12
 with sigma of 0.02
 C31-B1 \\sim C31A-B1 \\sim C23-B1 \\sim C39-B1 \\sim C47-B1
 with sigma of 0.02
 C32A-C31A \\sim C32-C31 \\sim C36A-C31A \\sim C36-C31 \\sim C48-C47 \\sim
C52-C47 \\sim C44-C39 \\sim C40-
 C39 \\sim C28-C23 \\sim C24-C23
 with sigma of 0.02
 C33A-C32A \\sim C33-C32 \\sim C36A-C35A \\sim C36-C35 \\sim C44-C43 \\sim
C41-C40 \\sim C28-C27 \\sim C25-
 C24 \\sim C52-C51 \\sim C49-C48
 with sigma of 0.02
 C34-C33 \\sim C34A-C33A \\sim C35A-C34A \\sim C35-C34 \\sim C42-C41 \\sim
C43-C42 \\sim C27-C26 \\sim C26-
 C25 \\sim C51-C50 \\sim C50-C49
 with sigma of 0.02
 F14A-C45 \\sim F13A-C45 \\sim F15A-C45
 with sigma of 0.02
 F14A-C45 \\sim F13-C45 \\sim F13A-C45 \\sim F15-C45 \\sim F15A-C45 \\sim
F14-C45
 with sigma of 0.02
 F13A-F14A \\sim F13A-F15A \\sim F14A-F15A
 with sigma of 0.02
 F4-C29 \\sim F4A-C29A
 with sigma of 0.02
 F5-C29 \\sim F5A-C29A
 with sigma of 0.02
 F6-C29 \\sim F6A-C29A
 with sigma of 0.02
 C27-C29 \\sim C27-C29A
 with sigma of 0.02
 F4-F5 \\sim F4A-F5A
 with sigma of 0.04
 F4-F6 \\sim F4A-F6A
 with sigma of 0.04
 F4-C27 \\sim F4A-C27
 with sigma of 0.04
 F5-F6 \\sim F5A-F6A
 with sigma of 0.04
 F5-C27 \\sim F5A-C27
 with sigma of 0.04
 F6-C27 \\sim F6A-C27
 with sigma of 0.04
 C29-C27 \\sim C29A-C27
 with sigma of 0.02
 F4A-C29A \\sim F4-C29 \\sim F5-C29 \\sim F5A-C29A \\sim F6-C29 \\sim F6A-C29A
 with sigma of 0.02
 Sn1-C7A \\sim Sn1-C7
 with sigma of 0.02
 C8-C7 \\sim C9-C7
 with sigma of 0.02
 C8A-C8 \\sim C9-C10
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C19 \\sim C20 \\sim C21 \\sim C22 \\sim C19A \\sim C20A \\sim C21A \\sim C22A:
within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
F7 \\sim F8 \\sim F9 \\sim F10 \\sim F11 \\sim F12 \\sim C31 \\sim C32 \\sim
C33 \\sim C34 \\sim C35 \\sim C36 \\sim C37 \\sim C38 \\sim F7A \\sim F8A \\sim
F9A \\sim F10A \\sim F11A \\sim F12A \\sim C31A \\sim C32A \\sim C33A \\sim
C34A \\sim C35A \\sim C36A \\sim C37A \\sim C38A: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08
F13 \\sim F14 \\sim F15 \\sim C45 \\sim F13A \\sim F15A \\sim F14A: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08
Sn1 \\sim C11 \\sim C12 \\sim C13 \\sim C14: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
Sn1: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
C56A \\sim C55A \\sim N1: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
O1 \\sim C55 \\sim C56 \\sim C57 \\sim C58: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
F4 \\sim F5 \\sim F6 \\sim C29 \\sim F6A \\sim F4A \\sim F5A \\sim C29A: within
2A with sigma of 0.04 and sigma for terminal atoms of 0.08
C7 \\sim C8 \\sim C9 \\sim C10: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
Uanis(B1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C19, C20, C21, C22, C19A, C20A, C21A, C22A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F7, F8, F9, F10, F11, F12, C31, C32, C33, C34, C35, C36, C37, C38, F7A, F8A,
 F9A, F10A, F11A, F12A, C31A, C32A, C33A, C34A, C35A, C36A, C37A, C38A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F13, F14, F15, C45, F13A, F15A, F14A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Sn1, C11, C12, C13, C14
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Sn1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C56A, C55A, N1, Sn1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O1, C55, C56, C57, C58
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F4, F5, F6, C29, F6A, F4A, F5A, C29A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7, C8, C9, C10
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C19A)=Sof(H19C)=Sof(H19D)=Sof(C20A)=Sof(H20C)=Sof(H20D)=Sof(C21A)=
 Sof(H21C)=Sof(H21D)=Sof(C22A)=Sof(H22D)=Sof(H22E)=Sof(H22F)=1-FVAR(1)
 Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C21)=Sof(H21A)=
 Sof(H21B)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=FVAR(1)
 Sof(F13A)=Sof(F15A)=Sof(F14A)=1-FVAR(2)
 Sof(F13)=Sof(F14)=Sof(F15)=FVAR(2)
 Sof(F4A)=Sof(F5A)=Sof(F6A)=Sof(C29A)=1-FVAR(3)
 Sof(C29)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(3)
 Fixed Sof: O1(0.5) C55(0.5) H55A(0.5) H55B(0.5) C56(0.5) H56A(0.5) H56B(0.5)
 C57(0.5) H57A(0.5) H57B(0.5) C58(0.5) H58A(0.5) H58B(0.5) N1(0.5) C55A(0.5)
 C56A(0.5) H56C(0.5) H56D(0.5) H56E(0.5) F7(0.5) F8(0.5) F9(0.5) F10(0.5)
 F11(0.5) F12(0.5) C31(0.5) C32(0.5) H32(0.5) C33(0.5) C34(0.5) H34(0.5)
 C35(0.5) C36(0.5) H36(0.5) C37(0.5) C38(0.5) F7A(0.5) F8A(0.5) F9A(0.5)
 F10A(0.5) F11A(0.5) F12A(0.5) C31A(0.5) C32A(0.5) H32A(0.5) C33A(0.5)
 C34A(0.5) H34A(0.5) C35A(0.5) C36A(0.5) H36A(0.5) C37A(0.5) C38A(0.5) C7(0.5)
 H7A(0.5) H7B(0.5) C8(0.5) H8A(0.5) H8B(0.5) C9(0.5) H9A(0.5) H9B(0.5) C10(0.5)
 H10A(0.5) H10B(0.5) C7A(0.5) H7AA(0.5) H7AB(0.5) C8A(0.5) H8AA(0.5) H8AB(0.5)
 C9A(0.5) H9AA(0.5) H9AB(0.5) H9AC(0.5) C10A(0.5) H10C(0.5) H10D(0.5) H10E(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B), C16(H16A,
 H16B), C17(H17A,H17B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B),
 C55(H55A,H55B), C56(H56A,H56B), C57(H57A,H57B), C58(H58A,H58B), C19A(H19C,
 H19D), C20A(H20C,H20D), C21A(H21C,H21D), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B),
  C10(H10A,H10B), C7A(H7AA,H7AB), C8A(H8AA,H8AB)
6.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C26(H26), C28(H28), C32(H32), C34(H34), C36(H36), C40(H40),
 C42(H42), C44(H44), C48(H48), C50(H50), C52(H52), C32A(H32A), C34A(H34A),
 C36A(H36A)
6.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C18(H18A,H18B,H18C), C22(H22A,H22B,H22C), C56A(H56C,H56D,
 H56E), C22A(H22D,H22E,H22F), C9A(H9AA,H9AB,H9AC), C10A(H10C,H10D,H10E)
;
_shelx_res_checksum              74326
_olex2_submission_special_instructions 'No special instructions were received'