Electrooxidative o-Carborane Chalcogenations Without Directing Groups: Cage Activation by Copper Catalysis at Room Temperature
Yang, Long; Jei, Becky Bongsuiru; Scheremetjew, Alexej; Yuan, Binbin; Stückl, A Claudia; Ackermann, Lutz; Chemical Science  (2021) –; doi:10.1039/D1SC02905C

data_1564524
_publ_section_title
;
 Electrooxidative o-Carborane Chalcogenations Without Directing Groups:
 Cage Activation by Copper Catalysis at Room Temperature
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02905C
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H24 B10 S'
_chemical_formula_sum            'C19 H24 B10 S'
_chemical_formula_weight         392.54
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-02-26 deposited with the CCDC.	2021-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.8557(17)
_cell_length_b                   12.6391(11)
_cell_length_c                   6.8918(6)
_cell_measurement_reflns_used    9199
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.517
_cell_measurement_theta_min      3.220
_cell_volume                     2078.0(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture CuMo Dual Source'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            136112
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.569
_diffrn_reflns_theta_min         2.348
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9107
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1461 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.9107.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       plank
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.454
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2847 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         6375
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0254
_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^)+(0.0439P)^2^+0.2709P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0703
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                6245
_reflns_number_total             6375
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02905c2.cif
_cod_data_source_block           1284_pna21
_cod_database_code               1564524
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C11(H11), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_olex2_submission_special_instructions 'No special instructions were received'