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_7243349
_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         'C22 H27 O2 P'
_chemical_formula_sum            'C22 H27 O2 P'
_chemical_formula_weight         354.40
_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             2020-09-15
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_audit_update_record
;
2020-12-22 deposited with the CCDC.	2021-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                62.5460(10)
_cell_angle_beta                 81.2320(10)
_cell_angle_gamma                88.0550(10)
_cell_formula_units_Z            4
_cell_length_a                   10.80490(10)
_cell_length_b                   13.8758(2)
_cell_length_c                   14.4304(2)
_cell_measurement_reflns_used    34167
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      76.1280
_cell_measurement_theta_min      3.4370
_cell_volume                     1895.79(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     92.00 177.00   0.50    0.20    --  104.75  45.00 -60.00  170
  2  \w     92.00 178.00   0.50    0.20    --  104.75  30.00-120.00  172
  3  \w     92.00 178.00   0.50    0.20    --  104.75  30.00 -90.00  172
  4  \w     88.00 178.00   0.50    0.20    --  104.75  61.00 120.00  180
  5  \w     91.00 176.00   0.50    0.20    --  104.75  15.00 150.00  170
  6  \w    -34.00  26.00   0.50    0.05    --  -47.20  38.00 -60.00  120
  7  \w     -4.00  28.00   0.50    0.05    --  -47.20  19.00  30.00   64
  8  \w     -4.00  28.00   0.50    0.05    --  -47.20  19.00  90.00   64
  9  \w     -4.00  28.00   0.50    0.05    --  -47.20  19.00-120.00   64
 10  \w     32.00 116.00   0.50    0.20    --  104.75-132.00 -94.02  168
 11  \w     32.00 112.00   0.50    0.20    --  104.75-125.00-180.00  160
 12  \w     18.00  95.00   0.50    0.05    --   47.20-125.00-180.00  154
 13  \w     32.00 112.00   0.50    0.20    --  104.75-125.00-150.00  160
 14  \w     32.00 112.00   0.50    0.20    --  104.75-125.00-120.00  160
 15  \w     32.00 112.00   0.50    0.20    --  104.75-125.00 -60.00  160
 16  \w     32.00 115.00   0.50    0.20    --  104.75-130.00  -7.52  166
 17  \w     32.00 112.00   0.50    0.20    --  104.75-125.00 150.00  160
 18  \w     32.00 106.00   0.50    0.20    --  104.75 -94.00   0.00  148
 19  \w     32.00 106.00   0.50    0.20    --  104.75 -94.00  30.00  148
 20  \w     32.00 106.00   0.50    0.20    --  104.75 -94.00 -30.00  148
 21  \w     32.00 106.00   0.50    0.20    --  104.75 -94.00 -60.00  148
 22  \w    -24.00  72.00   0.50    0.05    --   47.20 -81.00-145.00  192
 23  \w     32.00 106.00   0.50    0.20    --  104.75 -94.00-180.00  148
 24  \w     32.00 129.00   0.50    0.20    --  104.75 -81.00-145.00  194
 25  \w     32.00 128.00   0.50    0.20    --  104.75 -77.00 -30.00  192
 26  \w     32.00  80.00   0.50    0.20    --  104.75 -61.00   0.00   96
 27  \w     32.00  80.00   0.50    0.20    --  104.75 -61.00  30.00   96
 28  \w     32.00 128.00   0.50    0.20    --  104.75 -77.00  60.00  192
 29  \w     32.00  80.00   0.50    0.20    --  104.75 -61.00 150.00   96
 30  \w     84.00 178.00   0.50    0.20    --  104.75  81.00 -23.00  188
 31  \w    -27.00  12.00   0.50    0.05    --   47.20 -19.00 -90.00   78
 32  \w    -27.00  12.00   0.50    0.05    --   47.20 -19.00  60.00   78
 33  \w    -72.00  26.00   0.50    0.05    --  -47.20  81.00 -23.00  196
 34  \w    -72.00 -29.00   0.50    0.20    -- -102.00  61.00  30.00   86
 35  \w    -72.00 -29.00   0.50    0.20    -- -102.00  61.00-180.00   86
 36  \w   -122.00 -29.00   0.50    0.20    -- -102.00 139.00-143.02  186
 37  \w   -120.00 -29.00   0.50    0.20    -- -102.00 136.00 -13.60  182
 38  \w   -112.00 -29.00   0.50    0.20    -- -102.00 125.00  90.00  166
 39  \w   -112.00 -29.00   0.50    0.20    -- -102.00 125.00  60.00  166
 40  \w   -126.00 -29.00   0.50    0.20    -- -102.00  81.00 -23.00  194
 41  \w   -174.00 -88.00   0.50    0.20    -- -102.00 -43.00  62.92  172
 42  \w   -174.00 -89.00   0.50    0.20    -- -102.00 -45.00  90.00  170
 43  \w   -120.00 -24.00   0.50    0.05    --  -47.20 -77.00 150.00  192
 44  \w   -120.00 -32.00   0.50    0.05    --  -47.20 -57.00 150.00  176
 45  \w   -120.00 -24.00   0.50    0.05    --  -47.20 -77.00  60.00  192
 46  \w   -120.00 -42.00   0.50    0.05    --  -47.20 -57.00  60.00  156
 47  \w   -120.00 -24.00   0.50    0.05    --  -47.20 -77.00 -30.00  192
 48  \w   -120.00 -24.00   0.50    0.05    --  -47.20 -77.00-120.00  192
 49  \w   -120.00 -32.00   0.50    0.05    --  -47.20 -57.00 -30.00  176
 50  \w   -175.00 -84.00   0.50    0.20    -- -102.00 -65.00-119.13  182
 51  \w   -175.00 -80.00   0.50    0.20    -- -102.00 -81.00-145.00  190
 52  \w   -120.00 -74.00   0.50    0.05    --  -47.20-125.00-150.00   92
 53  \w   -120.00 -74.00   0.50    0.05    --  -47.20-125.00   0.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0751838000
_diffrn_orient_matrix_UB_12      0.0921590000
_diffrn_orient_matrix_UB_13      0.0096251000
_diffrn_orient_matrix_UB_21      0.0763248000
_diffrn_orient_matrix_UB_22      0.0837296000
_diffrn_orient_matrix_UB_23      -0.1044586000
_diffrn_orient_matrix_UB_31      -0.0968015000
_diffrn_orient_matrix_UB_32      -0.0132980000
_diffrn_orient_matrix_UB_33      -0.0618249000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            44733
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.129
_diffrn_reflns_theta_min         3.493
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.368
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             760
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         7445
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0464P)^2^+0.6253P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0932
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6881
_reflns_number_total             7445
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra04947j2.cif
_cod_data_source_block           cm_uj01_lt2
_cod_depositor_comments
;

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C44 H54 O4 P2'
_cod_original_formula_weight         708.81
_cod_original_formula_moiety         '2(C22 H27 O2 P)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1895.79(4)
_cod_database_code               7243349
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C10 H10 O4 P'
_diffrn_oxdiff_digest_frames
;
0182b66c26e9c931beb7beb84ca74003ed00043f749
;
_diffrn_oxdiff_digest_hkl
;
013d58e9e51863d93269314358b85f79eff0b0
;
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 Ternary CH refined with riding coordinates:
 C2(H2), C31(H31), C6(H6), C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C5(H5A,H5B), C30(H30A,H30B), C3(H3A,H3B), C23(H23A,H23B),
 C24(H24A,H24B), C4(H4A,H4B), C49(H49A,H49B), C28(H28A,H28B), C29(H29A,H29B),
 C50(H50A,H50B), C48(H48A,H48B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C36(H36), C17(H17), C42(H42), C8(H8), C35(H35), C40(H40), C33(H33),
 C41(H41), C10(H10), C34(H34), C15(H15), C9(H9), C16(H16)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C45(H45A,H45B,H45C), C47(H47A,H47B,H47C), C22(H22A,H22B,
 H22C)
;
_shelx_res_checksum              11869
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.203
_oxdiff_exptl_absorpt_empirical_full_min 0.473