Sonogashira Coupling of the Ethynyl Monocarborane [CB11H11-12-CCH]–
Duttwyler, Simon; Liu, Fan; Chen, Tao; Zhang, Kang; Jiang, Tao; Liu, Jiyong; Dalton Transactions  (2022) –; doi:10.1039/D2DT01048H

data_7710621
_publ_section_title
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 Sonogashira Coupling of the Ethynyl Monocarborane [CB11H11-12-CCH]--
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT01048H
_journal_year                    2022
_chemical_formula_moiety         '2(C21 H26 B11 P), C3 H6 O'
_chemical_formula_sum            'C45 H58 B22 O P2'
_chemical_formula_weight         914.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-27 deposited with the CCDC.	2022-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.944(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   32.0811(11)
_cell_length_b                   12.8344(4)
_cell_length_c                   13.7547(5)
_cell_measurement_reflns_used    8956
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.47
_cell_volume                     5356.6(3)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21870
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.108
_diffrn_reflns_theta_min         2.176
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1224 before and 0.0460 after correction.
The Ratio of minimum to maximum transmission is 0.9282.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5903
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0562P)^2^+3.8889P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1180
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4934
_reflns_number_total             5903
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt01048h2.cif
_cod_data_source_block           mo_220114_pph3_0m
_cod_database_code               7710621
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.946
_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. Restrained distances
 C23-C24
 1.53 with sigma of 0.02
 C23-C22
 1.53 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O1 \\sim C22 \\sim C23 \\sim C24: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Fixed Sof: O1(0.5) C22(0.5) H22A(0.5) H22B(0.5) H22C(0.5) C23(0.5) C24(0.5)
 H24A(0.5) H24B(0.5) H24C(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
5.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
5.c Boron cage BH refined with riding coordinates:
 C1(H1), B1(H1A), B2(H2), B3(H3), B4(H4), B5(H5A), B6(H6A), B7(H7A), B8(H8A),
 B9(H9A), B10(H10)
;
_shelx_res_checksum              25818
_shelx_hkl_checksum              25579
_olex2_submission_special_instructions 'No special instructions were received'