Copper-Catalyzed Suzuki-Miyaura Coupling of Arylboronate Esters: Transmetalation with (PN)CuF and Identification of Intermediates.
Gurung, Santosh K.; Thapa, Surendra; Kafle, Arjun; Dickie, Diane A.; Giri, Ramesh; Organic letters 16 (2014) 1264–1267; doi:10.1021/ol500310u

data_1513450
_publ_section_title
;
 Copper-Catalyzed Suzuki-Miyaura Coupling of Arylboronate Esters:
 Transmetalation with (PN)CuF and Identification of Intermediates.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              1264
_journal_page_last               1267
_journal_paper_doi               10.1021/ol500310u
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C22 H33 Cu N P'
_chemical_formula_weight         406.00
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.6292(13)
_cell_length_b                   9.3181(8)
_cell_length_c                   12.5012(9)
_cell_measurement_reflns_used    1958
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      23.59
_cell_measurement_theta_min      2.44
_cell_volume                     2170.1(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      101(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.969
_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     0.1354
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.511
_diffrn_reflns_point_group_measured_fraction_max 0.508
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.988
_diffrn_reflns_theta_min         2.444
_exptl_absorpt_coefficient_mu    1.084
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.062
_refine_diff_density_max         1.062
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details
; 
No quotients, so Flack parameter determined by classical intensity fit 
;
_refine_ls_abs_structure_Flack   0.09(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2162
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0629
_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^)+(0.0593P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1249
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    0.000
_reflns_Friedel_fraction_max     0.000
_reflns_number_gt                1394
_reflns_number_total             2162
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol500310u_si_004.cif
_cod_data_source_block           twin4
_cod_database_code               1513450
_shelx_estimated_absorpt_t_min   0.796
_shelx_estimated_absorpt_t_max   0.936
_shelxl_version_number           2013-4
_shelx_res_checksum              95031
_shelx_hkl_checksum              38963