Evaluation of P-bridged biaryl phosphine ligands in palladium-catalysed Suzuki–Miyaura cross-coupling reactions
Lamola, Jairus L.; Moshapo, Paseka T.; Holzapfel, Cedric W.; Maumela, Munaka Christopher; RSC Advances 11 (2021) 26883–26891; doi:10.1039/D1RA04947J

data_7243352
_publ_section_title
;
 Evaluation of P-bridged biaryl phosphine ligands in palladium-catalysed
 Suzuki--Miyaura cross-coupling reactions
;
_journal_issue                   43
_journal_name_full               'RSC Advances'
_journal_page_first              26883
_journal_page_last               26891
_journal_paper_doi               10.1039/D1RA04947J
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C24 H30 N O3 P'
_chemical_formula_sum            'C24 H30 N O3 P'
_chemical_formula_weight         411.20
_chemical_name_systematic
N,N-dimethyl-2'-((1R,3S,5S,7R)-1,3,5,7-tetramethyl-2,4,6-trioxa-8-phosphaadamantan-8-yl)-[1,1'-biphenyl]-2-amine
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-12-22
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2020-12-22 deposited with the CCDC.	2021-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.975(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.219(2)
_cell_length_b                   8.4649(8)
_cell_length_c                   24.795(2)
_cell_measurement_reflns_used    9153
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.67
_cell_measurement_theta_min      2.58
_cell_volume                     4550.4(7)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0480
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            91270
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.259
_diffrn_reflns_theta_min         1.759
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.7110
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0613 before and 0.0579 after correction.
The Ratio of minimum to maximum transmission is 0.9540.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_description       block
_exptl_crystal_F_000             2220
_exptl_crystal_preparation       THF/Acetone
_exptl_crystal_recrystallization_method 'At 0^oC for 48 h'
_exptl_crystal_size_max          0.465
_exptl_crystal_size_mid          0.346
_exptl_crystal_size_min          0.281
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0445P)^2^+2.7285P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0971
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3906
_reflns_number_total             4612
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra04947j2.cif
_cod_data_source_block           mo_20jl_cgdavephos_rt_solve_a
_cod_depositor_comments
;

2025-03-06
Z value fixed to be consistent with given formula
                 miguel
;
_cod_original_formula_units_Z            60
_cod_original_cell_volume        4550.3(8)
_cod_database_code               7243352
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.844
_shelx_estimated_absorpt_t_min   0.760
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00E(H00C,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C00G(H00E,H00F,H00G), C00L(H00H,H00I,H00J), C00O(H00K,H00L,H00M), C00P(H00N,
 H00O,H00P), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              66554
_olex2_submission_original_sample_id JerryPhos
_olex2_submission_special_instructions 'No special instructions were received'