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_4518186
_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         'C68 H40 Cl2 Cu2 F24 P4, 3(C4 H8 O)'
_chemical_formula_sum            'C80 H64 Cl2 Cu2 F24 O3 P4'
_chemical_formula_weight         1851.17
_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     dual
_audit_creation_date             2020-07-14
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                69.9060(10)
_cell_angle_beta                 77.0810(10)
_cell_angle_gamma                64.8240(10)
_cell_formula_units_Z            2
_cell_length_a                   16.4338(8)
_cell_length_b                   16.5229(8)
_cell_length_c                   17.2231(8)
_cell_measurement_reflns_used    9911
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.66
_cell_measurement_theta_min      2.31
_cell_volume                     3958.2(3)
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 8.258
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            71380
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         1.264
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  0.5624
_exptl_absorpt_correction_T_min  0.5371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0503 before and 0.0429 after correction. The Ratio of minimum to maximum transmission is 0.9482. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.226
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1059
_refine_ls_number_reflns         14506
_refine_ls_number_restraints     65
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0627P)^2^+9.8178P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1425
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10889
_reflns_number_total             14506
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c03622_si_003.cif
_cod_data_source_block           engle243
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        3958.3(3)
_cod_database_code               4518186
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.897
_shelx_estimated_absorpt_t_min   0.871
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 O2-C8S \\sim O2-C8T
 with sigma of 0.005
 C8S-C7S \\sim C8T-C7S
 with sigma of 0.005
 F3-C13 \\sim F2A-C13 \\sim F2-C13 \\sim F1A-C13 \\sim F1-C13 \\sim F3A-C13
 with sigma of 0.01
 F5-C20 \\sim F5A-C20 \\sim F4-C20 \\sim F4A-C20 \\sim F6-C20 \\sim F6A-C20
 with sigma of 0.01
 F4A-F5A \\sim F5A-F6A \\sim F4A-F6A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C8T) = Uanis(C8S)
Uanis(F3) = Uanis(F1A)
Uanis(F2) = Uanis(F3A)
Uanis(F1) = Uanis(F2A)
Uanis(F5) = Uanis(F4A)
Uanis(F4) = Uanis(F6A)
Uanis(F5A) = Uanis(F6)
4. Rigid body (RIGU) restrains
 O3, C12S, C11S, C10S, C9S
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H7SC)=Sof(H7SD)=Sof(C8T)=Sof(H8TA)=Sof(H8TB)=1-FVAR(1)
 Sof(H7SA)=Sof(H7SB)=Sof(C8S)=Sof(H8SA)=Sof(H8SB)=FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(2)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C5S(H5SA,H5SB), C6S(H6SA,H6SB), C7S(H7SA,H7SB), C7S(H7SC,H7SD), C8S(H8SA,
 H8SB), C1S(H1SA,H1SB), C2S(H2SA,H2SB), C3S(H3SA,H3SB), C4S(H4SA,H4SB),
 C9S(H9SA,H9SB), C10S(H10A,H10B), C11S(H11A,H11B), C12S(H12A,H12B), C8T(H8TA,
 H8TB)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C15(H15),
 C16(H16), C18(H18), C19(H19), C22(H22), C23(H23), C25(H25), C26(H26), C29(H29),
  C30(H30), C32(H32), C33(H33), C36(H36), C37(H37), C38(H38), C39(H39),
 C42(H42), C43(H43), C45(H45), C46(H46), C49(H49), C50(H50), C52(H52), C53(H53),
  C56(H56), C57(H57), C59(H59), C60(H60), C63(H63), C64(H64), C66(H66), C67(H67)
;
_shelx_res_checksum              20260
_shelx_hkl_checksum              97324
_olex2_submission_special_instructions 'No special instructions were received'