Catalytic regioselective 3,4-difunctionalization of 3-iodo-<i>o</i>-carborane <i>via</i> Pd migration.
Jiang, Xianren; Ding, Chang-Hua; Qiu, Zaozao; Xie, Zuowei; Dalton transactions (Cambridge, England : 2003) 54 (2025) 8764–8768; doi:10.1039/d5dt00981b

data_7718657
_publ_section_title
;
 Catalytic regioselective 3,4-difunctionalization of
 3-iodo-<i>o</i>-carborane <i>via</i> Pd migration.
;
_journal_issue                   22
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8764
_journal_page_last               8768
_journal_paper_doi               10.1039/d5dt00981b
_journal_volume                  54
_journal_year                    2025
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C16 H29 B10 N'
_chemical_formula_sum            'C16 H29 B10 N'
_chemical_formula_weight         343.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-05
_audit_creation_method
;
Olex2 1.5
(compiled 2025.02.27 svn.r83f5de26 for OlexSys, GUI svn.r7172)
;
_audit_update_record
;
2025-04-10 deposited with the CCDC.	2025-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.1120(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.71890(10)
_cell_length_b                   18.2589(3)
_cell_length_c                   8.21790(10)
_cell_measurement_reflns_used    9442
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      54.85
_cell_measurement_theta_min      4.70
_cell_volume                     1004.16(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10490
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.827
_diffrn_reflns_theta_min         4.700
_diffrn_source_current           3.57
_diffrn_source_power             0.2491146
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1652 before and 0.0760 after correction.
The Ratio of minimum to maximum transmission is 0.7027.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1505 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3604
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0532P)^2^+0.2259P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_full    0.910
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                3395
_reflns_number_total             3604
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt00981b2.cif
_cod_data_source_block           5f
_cod_depositor_comments
'Adding full bibliography for 7718655--7718657.cif.'
_cod_database_code               7718657
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.955
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C12(H12), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C6(H6), C8(H8)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
2.e Boron cage BH refined with riding coordinates:
 C1(H1A), C2(H2), B5(H5A), B6(H6A), B7(H7), B8(H8A), B9(H9), B10(H10A),
 B11(H11), B12(H12A)
;
_shelx_res_checksum              64415
_shelx_hkl_checksum              3669
_olex2_submission_special_instructions 'No special instructions were received'