Silylene-Copper(I) Catalysis: Regioselective Protoboration of Terminal Alkynes
Kaulage, Sandeep; Shah, Brij; Sharma, Himanshu; Panday, Rishukumar; Vanka, Kumar; Khan, Shabana; Chemical Communications  (2025) –; doi:10.1039/D5CC06125C

data_7135169
_publ_section_title
;
 Silylene-Copper(I) Catalysis: Regioselective Protoboration of Terminal
 Alkynes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D5CC06125C
_journal_year                    2025
_chemical_formula_moiety         'C42 H65 Cu N3 P Si'
_chemical_formula_sum            'C42 H65 Cu N3 P Si'
_chemical_formula_weight         734.57
_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     iterative
_audit_creation_date             2025-07-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-08-07 deposited with the CCDC.	2025-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.685(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.0396(10)
_cell_length_b                   19.1146(18)
_cell_length_c                   11.9680(11)
_cell_measurement_reflns_used    7030
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      21.36
_cell_measurement_theta_min      2.24
_cell_volume                     2086.8(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1461
_diffrn_reflns_av_unetI/netI     0.1930
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22290
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.213
_diffrn_reflns_theta_max         25.213
_diffrn_reflns_theta_min         1.873
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1306 before and 0.0900 after correction.
The Ratio of minimum to maximum transmission is 0.7303.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.252
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.182
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
;
 Flack x determined using 1349 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.028(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     450
_refine_ls_number_reflns         7212
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1441
_refine_ls_R_factor_gt           0.0683
_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^)+(0.0147P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0984
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_full    0.922
_reflns_Friedel_fraction_max     0.922
_reflns_number_gt                4409
_reflns_number_total             7212
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06125c2.cif
_cod_data_source_block           C6
_cod_database_code               7135169
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.895
_shelx_estimated_absorpt_t_min   0.859
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.1
3.a Ternary CH refined with riding coordinates:
 C16(H16), C19(H19), C28(H28), C31(H31)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C24(H24), C25(H25), C26(H26),
 C36(H36), C38(H38)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,
 H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C29(H29A,H29B,H29C),
 C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C40(H40A,H40B,
 H40C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C)
;
_shelx_res_checksum              38254
_shelx_hkl_checksum              76161
_olex2_submission_special_instructions 'No special instructions were received'