Synthesis and cluster structure distortions of biscarborane dithiol, thioether, and disulfide.
Riffle, Jared R.; Hemingway, Tyler M.; Smith, Mark D.; Peryshkov, Dmitry V.; Dalton transactions (Cambridge, England : 2003) 53 (2024) 4444–4450; doi:10.1039/d3dt04289h

data_7715076
_publ_section_title
;
 Synthesis and cluster structure distortions of biscarborane dithiol,
 thioether, and disulfide.
;
_journal_issue                   10
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4444
_journal_page_last               4450
_journal_paper_doi               10.1039/d3dt04289h
_journal_volume                  53
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C4 H20 B20 S2, 2(C16 H36 N)'
_chemical_formula_sum            'C36 H92 B20 N2 S2'
_chemical_formula_weight         833.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-12-13 deposited with the CCDC.	2024-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.059(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   43.403(10)
_cell_length_b                   11.311(3)
_cell_length_c                   20.644(5)
_cell_measurement_reflns_used    9218
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.577
_cell_measurement_theta_min      2.308
_cell_volume                     9873(4)
_computing_cell_refinement       'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_h_min       -51
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            70274
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.025
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1497 before and 0.0575 after correction. 
The Ratio of minimum to maximum transmission is 0.9173. 
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.121
_exptl_crystal_description       plate
_exptl_crystal_F_000             3632
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
;
 Flack x determined using 5581 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1095
_refine_ls_number_reflns         17370
_refine_ls_number_restraints     219
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1161
_refine_ls_R_factor_gt           0.0964
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1779P)^2^+15.8968P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2530
_refine_ls_wR_factor_ref         0.2733
_reflns_Friedel_coverage         0.998
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                14050
_reflns_number_total             17370
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt04289h2.cif
_cod_data_source_block           th01085b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7715071--7715076.cif.
;
_cod_database_code               7715076
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.949
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{N4A, N4B}
3. Restrained distances
 C48-C50B = C48-C50A = C47-C49A = C47-C49B
 2.5 with sigma of 0.015
 C41B-C40 \\sim C41A-C40 \\sim C33-C32 \\sim C29-C28 \\sim C36-C37A \\sim
C36-C37B \\sim C56A-C57A ~
 C56B-C57B \\sim C48-C49A \\sim C48-C49B
 with sigma of 0.01
 C42B-C41B \\sim C42A-C41A \\sim C34-C33 \\sim C30-C29 \\sim C37A-C38A \\sim
C37B-C38B \\sim C57A-C58A
 \\sim C57B-C58B \\sim C49A-C50A \\sim C49B-C50B
 with sigma of 0.01
 C56B-C55 \\sim C56A-C55 \\sim C44-C43 \\sim C52-C51 \\sim C47-C48
 with sigma of 0.01
 N3-C44 \\sim N3-C48 \\sim N3-C52 \\sim N3-C56A \\sim N3-C56B
 with sigma of 0.01
4. Rigid bond restraints
 C53, C54
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
Uiso(N4A) = Uiso(N4B)
Uiso(C68A) = Uiso(C68B)
Uanis(C41A) = Uanis(C41B)
Uanis(C37A) = Uanis(C37B)
Uanis(C56A) = Uanis(C56B)
Uiso(C57A) = Uiso(C57B)
Uiso(C49A) = Uiso(C49B)
Uiso(C50A) = Uiso(C50B)
Uiso(C74B) = Uiso(C74A)
Uiso(C70B) = Uiso(C69A)
Uiso(C72B) = Uiso(C72A)
Uiso(C71A) = Uiso(C71B)
6. Same fragment restrains
{N1, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25,
C26} sigma for 1-2: 0.02, 1-3: 0.04
as
{N4A, C59A, C60A, C61A, C62A, C63A, C64A, C65A, C66A, C67A, C68A, C69A, C70A,
C71A, C72A, C73A, C74A}
{N1, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25,
C26} sigma for 1-2: 0.02, 1-3: 0.04
as
{N4B, C59B, C60B, C61B, C62B, C63B, C64B, C65B, C66B, C67B, C68B, C69B, C70B,
C71B, C72B, C73B, C74B}
7. Others
 Sof(H40C)=Sof(H40D)=Sof(C41B)=Sof(H41C)=Sof(H41D)=Sof(C42B)=Sof(H42D)=
 Sof(H42E)=Sof(H42F)=1-FVAR(1)
 Sof(H40A)=Sof(H40B)=Sof(C41A)=Sof(H41A)=Sof(H41B)=Sof(C42A)=Sof(H42A)=
 Sof(H42B)=Sof(H42C)=FVAR(1)
 Sof(H36C)=Sof(H36D)=Sof(C37B)=Sof(H37C)=Sof(H37D)=Sof(C38B)=Sof(H38D)=
 Sof(H38E)=Sof(H38F)=1-FVAR(2)
 Sof(H36A)=Sof(H36B)=Sof(C37A)=Sof(H37A)=Sof(H37B)=Sof(C38A)=Sof(H38A)=
 Sof(H38B)=Sof(H38C)=FVAR(2)
 Sof(H55C)=Sof(H55D)=Sof(C56B)=Sof(H56C)=Sof(H56D)=Sof(C57B)=Sof(H57C)=
 Sof(H57D)=Sof(C58B)=Sof(H58D)=Sof(H58E)=Sof(H58F)=1-FVAR(3)
 Sof(H55A)=Sof(H55B)=Sof(C56A)=Sof(H56A)=Sof(H56B)=Sof(C57A)=Sof(H57A)=
 Sof(H57B)=Sof(C58A)=Sof(H58A)=Sof(H58B)=Sof(H58C)=FVAR(3)
 Sof(H48C)=Sof(H48D)=Sof(C49B)=Sof(H49C)=Sof(H49D)=Sof(C50B)=Sof(H50D)=
 Sof(H50E)=Sof(H50F)=1-FVAR(4)
 Sof(H48A)=Sof(H48B)=Sof(C49A)=Sof(H49A)=Sof(H49B)=Sof(C50A)=Sof(H50A)=
 Sof(H50B)=Sof(H50C)=FVAR(4)
 Sof(C59B)=Sof(H59C)=Sof(H59D)=Sof(C60B)=Sof(H60C)=Sof(H60D)=Sof(C61B)=
 Sof(H61C)=Sof(H61D)=Sof(C62B)=Sof(H62D)=Sof(H62E)=Sof(H62F)=1-FVAR(5)
 Sof(C59A)=Sof(H59A)=Sof(H59B)=Sof(C60A)=Sof(H60A)=Sof(H60B)=Sof(C61A)=
 Sof(H61A)=Sof(H61B)=Sof(C62A)=Sof(H62A)=Sof(H62B)=Sof(H62C)=FVAR(5)
 Sof(C63B)=Sof(H63C)=Sof(H63D)=Sof(C64B)=Sof(H64C)=Sof(H64D)=Sof(C65B)=
 Sof(H65C)=Sof(H65D)=Sof(C66B)=Sof(H66D)=Sof(H66E)=Sof(H66F)=1-FVAR(6)
 Sof(C63A)=Sof(H63A)=Sof(H63B)=Sof(C64A)=Sof(H64A)=Sof(H64B)=Sof(C65A)=
 Sof(H65A)=Sof(H65B)=Sof(C66A)=Sof(H66A)=Sof(H66B)=Sof(H66C)=FVAR(6)
 Sof(C67B)=Sof(H67C)=Sof(H67D)=Sof(C68B)=Sof(H68C)=Sof(H68D)=Sof(C69B)=
 Sof(H69C)=Sof(H69D)=Sof(C70B)=Sof(H70D)=Sof(H70E)=Sof(H70F)=1-FVAR(7)
 Sof(C67A)=Sof(H67A)=Sof(H67B)=Sof(C68A)=Sof(H68A)=Sof(H68B)=Sof(C69A)=
 Sof(H69A)=Sof(H69B)=Sof(C70A)=Sof(H70A)=Sof(H70B)=Sof(H70C)=FVAR(7)
 Sof(C71B)=Sof(H71C)=Sof(H71D)=Sof(C72B)=Sof(H72C)=Sof(H72D)=Sof(C73B)=
 Sof(H73C)=Sof(H73D)=Sof(C74B)=Sof(H74D)=Sof(H74E)=Sof(H74F)=1-FVAR(8)
 Sof(C71A)=Sof(H71A)=Sof(H71B)=Sof(C72A)=Sof(H72A)=Sof(H72B)=Sof(C73A)=
 Sof(H73A)=Sof(H73B)=Sof(C74A)=Sof(H74A)=Sof(H74B)=Sof(H74C)=FVAR(8)
 Fixed Sof: N4A(0.5) N4B(0.5)
8.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),
 C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C27(H27A,H27B), C28(H28A,H28B),
  C29(H29A,H29B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C35(H35A,
 H35B), C36(H36A,H36B), C36(H36C,H36D), C37A(H37A,H37B), C37B(H37C,H37D),
 C39(H39A,H39B), C40(H40A,H40B), C40(H40C,H40D), C41A(H41A,H41B), C41B(H41C,
 H41D), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B), C47(H47A,H47B),
 C48(H48A,H48B), C48(H48C,H48D), C49A(H49A,H49B), C49B(H49C,H49D), C51(H51A,
 H51B), C52(H52A,H52B), C53(H53A,H53B), C55(H55A,H55B), C55(H55C,H55D),
 C56A(H56A,H56B), C57A(H57A,H57B), C56B(H56C,H56D), C57B(H57C,H57D), C59A(H59A,
 H59B), C60A(H60A,H60B), C61A(H61A,H61B), C63A(H63A,H63B), C64A(H64A,H64B),
 C65A(H65A,H65B), C67A(H67A,H67B), C68A(H68A,H68B), C69A(H69A,H69B), C71A(H71A,
 H71B), C72A(H72A,H72B), C73A(H73A,H73B), C59B(H59C,H59D), C60B(H60C,H60D),
 C61B(H61C,H61D), C63B(H63C,H63D), C64B(H64C,H64D), C65B(H65C,H65D), C67B(H67C,
 H67D), C68B(H68C,H68D), C69B(H69C,H69D), C71B(H71C,H71D), C72B(H72C,H72D),
 C73B(H73C,H73D)
8.b Idealised Me refined with riding coordinates:
 C50A(H50A,H50B,H50C), C50B(H50D,H50E,H50F), C58A(H58A,H58B,H58C), C58B(H58D,
 H58E,H58F), C62A(H62A,H62B,H62C), C66A(H66A,H66B,H66C), C70A(H70A,H70B,H70C),
 C74A(H74A,H74B,H74C), C62B(H62D,H62E,H62F), C66B(H66D,H66E,H66F), C70B(H70D,
 H70E,H70F), C74B(H74D,H74E,H74F)
8.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C18(H18A,H18B,H18C), C22(H22A,H22B,H22C), C26(H26A,H26B,
 H26C), C30(H30A,H30B,H30C), C34(H34A,H34B,H34C), C38A(H38A,H38B,H38C),
 C38B(H38D,H38E,H38F), C42A(H42A,H42B,H42C), C42B(H42D,H42E,H42F), C46(H46A,
 H46B,H46C), C54(H54A,H54B,H54C)
8.d Boron cage BH refined with riding coordinates:
 B1(H1), B2(H2), B3(H3), B4(H4), B5(H5), B6(H6), B7(H7), B8(H8), B9(H9),
 B10(H10), B11(H11), B12(H12), B13(H13), B14(H14), B15(H15), B16(H16), B17(H17),
  B18(H18), B19(H19), B20(H20), B21(H21), B22(H22), B23(H23), B24(H24),
 B25(H25), B26(H26), B27(H27), B28(H28), B29(H29), B30(H30), B31(H31), B32(H32),
  B33(H33), B34(H34), B35(H35), B36(H36), B37(H37), B38(H38), B39(H39), B40(H40)
;
_shelx_res_checksum              93546
_olex2_submission_special_instructions 'No special instructions were received'