Multifaceted Substrate‒Ligand Interactions Promote the Copper-Catalyzed Hydroboration of Benzylidenecyclobutanes and Related Compounds
Kang, Taeho; Erbay, Tuğçe G.; Xu, Kane L.; Gallego, Gary M.; Burtea, Alexander; Nair, Sajiv K.; Patman, Ryan L.; Zhou, Ru; Sutton, Scott C.; McAlpine, Indrawan J.; Liu, Peng; Engle, Keary M.; ACS Catalysis  (2020) 13075–13083; doi:10.1021/acscatal.0c03622

data_4518185
_publ_section_title
;
 Multifaceted Substrate--Ligand Interactions Promote the Copper-Catalyzed
 Hydroboration of Benzylidenecyclobutanes and Related Compounds
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              13075
_journal_page_last               13083
_journal_paper_doi               10.1021/acscatal.0c03622
_journal_year                    2020
_chemical_formula_moiety         'C60 H40 Cl2 Cu2 F8 P4, 2(C4 H8 O)'
_chemical_formula_sum            'C68 H56 Cl2 Cu2 F8 O2 P4'
_chemical_formula_weight         1378.98
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-12-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90.177(2)
_cell_angle_beta                 93.026(2)
_cell_angle_gamma                114.592(2)
_cell_formula_units_Z            2
_cell_length_a                   13.3478(9)
_cell_length_b                   14.0620(9)
_cell_length_c                   17.8249(12)
_cell_measurement_reflns_used    6367
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.60
_cell_measurement_theta_min      2.76
_cell_volume                     3036.8(4)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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_unetI/netI     0.0928
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24144
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.718
_diffrn_reflns_theta_min         1.593
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.965
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     776
_refine_ls_number_reflns         24144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0448P)^2^+2.1388P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1236
_reflns_Friedel_coverage         0.000
_reflns_number_gt                17007
_reflns_number_total             24144
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c03622_si_002.cif
_cod_data_source_block           engle223
_cod_database_code               4518185
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.869
_shelx_estimated_absorpt_t_min   0.788
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5180(7)
 0.4820(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C60(H60A,H60B), C61(H61A,H61B), C62(H62A,H62B), C55(H55A,H55B), C59(H59A,
 H59B), C58(H58A,H58B), C56(H56A,H56B), C57(H57A,H57B)
3.b Aromatic/amide H refined with riding coordinates:
 C64(H64), C50(H50), C33(H33), C20(H20), C66(H66), C15(H15), C17(H17),
 C65(H65), C54(H54), C24(H24), C38(H38), C36(H36), C32(H32), C14(H14), C48(H48),
  C16(H16), C67(H67), C53(H53), C12(H12), C30(H30), C2(H2), C44(H44), C21(H21),
 C6(H6), C35(H35), C47(H47), C27(H27), C8(H8), C3(H3), C29(H29), C39(H39),
 C26(H26), C41(H41), C45(H45), C42(H42), C23(H23), C5(H5), C51(H51), C11(H11),
 C9(H9)
;
_shelx_res_checksum              50164
_shelx_hkl_checksum              77308
_olex2_submission_special_instructions 'No special instructions were received'