Palladium-Catalyzed Suzuki‒Miyaura Cross-Couplings with 2-Diethylphosphonato-Substituted Aryl- and Naphthylboronate Esters as the Nucleophilic Partner: A Complementary Approach to the Synthesis of Biaryl Monophosphonates
Doherty, Simon; Knight, Julian G.; Ward, Nicholas A. B.; Perry, Daniel O.; Bittner, Dror M.; Probert, Michael R.; Westcott, Stephen A.; Organometallics 33 (2014) 5209–; doi:10.1021/om500520z

data_4084342
_publ_section_title
;
 Palladium-Catalyzed Suzuki--Miyaura Cross-Couplings with
 2-Diethylphosphonato-Substituted Aryl- and Naphthylboronate Esters as the
 Nucleophilic Partner: A Complementary Approach to the Synthesis of Biaryl
 Monophosphonates
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              5209
_journal_paper_doi               10.1021/om500520z
_journal_volume                  33
_journal_year                    2014
_chemical_formula_moiety         'C46 H35 Cl N P Pd'
_chemical_formula_sum            'C46 H35 Cl N P Pd'
_chemical_formula_weight         774.57
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-02-28
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4779)
;
_cell_angle_alpha                73.9259(16)
_cell_angle_beta                 73.7859(17)
_cell_angle_gamma                77.1431(17)
_cell_formula_units_Z            6
_cell_length_a                   13.5306(7)
_cell_length_b                   18.3786(10)
_cell_length_c                   22.8721(12)
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.517
_cell_measurement_theta_min      2.276
_cell_volume                     5182.5(5)
_computing_cell_refinement       'Apex2 - SAINT (Bruker 2013)'
_computing_data_collection       'Apex2 (Bruker 2013)'
_computing_data_reduction        'Apex2 - SAINT (Bruker 2013)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker Photon 100 Area Detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_unetI/netI     0.0929
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            76016
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.500
_diffrn_reflns_theta_max         27.591
_diffrn_reflns_theta_min         1.993
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1195 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.8678.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2376
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.074
_refine_diff_density_max         1.266
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1327
_refine_ls_number_reflns         23903
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0386P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.1038
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13981
_reflns_number_total             23903
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om500520z_si_002.cif
_cod_data_source_block           jgk130004
_cod_depositor_comments          'Adding full bibliography for 4084342.cif.'
_cod_database_code               4084342
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C3A(H3A), C3B(H3B), C10(H10), C10A(H10A), C10B(H10B)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), N1A(H1AA,H1AB), N1B(H1BA,H1BB)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C5A(H5A), C5B(H5B), C6(H6), C6A(H6A), C6B(H6B), C7(H7), C7A(H7A),
 C7B(H7B), C8(H8), C8A(H8A), C8B(H8B), C12(H12), C12A(H12A), C12B(H12B),
 C13(H13), C13A(H13A), C13B(H13B), C14(H14), C14A(H14A), C14B(H14B), C15(H15),
 C15A(H15A), C15B(H15B), C18(H18), C18A(H18A), C18B(H18B), C19(H19), C19A(H19A),
  C19B(H19B), C20(H20), C20A(H20A), C20B(H20B), C21(H21), C21A(H21A),
 C21B(H21B), C22(H22), C22A(H22A), C22B(H22B), C28(H28), C27(H27), C26(H26),
 C25(H25), C24(H24), C24A(H24A), C24B(H24B), C25A(H25A), C25B(H25B), C26A(H26A),
  C26B(H26B), C27A(H27A), C27B(H27B), C28A(H28A), C28B(H28B), C34(H34),
 C33(H33), C32(H32), C31(H31), C30(H30), C30A(H30A), C30B(H30B), C31A(H31A),
 C31B(H31B), C32A(H32A), C32B(H32B), C33A(H33A), C33B(H33B), C34A(H34A),
 C34B(H34B), C36(H36), C36A(H36A), C36B(H36B), C37(H37), C37A(H37A), C37B(H37B),
  C38(H38), C38A(H38A), C38B(H38B), C39(H39), C39A(H39A), C39B(H39B), C42(H42),
 C42A(H42A), C42B(H42B), C43(H43), C43A(H43A), C43B(H43B), C44(H44), C44A(H44A),
  C44B(H44B), C45(H45), C45A(H45A), C45B(H45B)
2.d Fitted hexagon refined as free rotating group:
 C23(C28,C27,C26,C25,C24), C29(C34,C33,C32,C31,C30)
;
_shelx_res_checksum              98134
_shelx_hkl_checksum              42390