Pd-catalysed, Ag-assisted C2–H alkenylation of benzophospholes
Tokura, Yu; Xu, Shibo; Kojima, Yuki; Miura, Masahiro; Hirano, Koji; Chemical Communications  (2022) –; doi:10.1039/D2CC04942B

data_7130851
_publ_section_title
;
 Pd-catalysed, Ag-assisted C2--H alkenylation of benzophospholes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04942B
_journal_year                    2022
_chemical_formula_moiety         'C26 H26 O4 P2'
_chemical_formula_sum            'C26 H26 O4 P2'
_chemical_formula_weight         464.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-06-22 deposited with the CCDC.	2022-10-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.026(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7292(2)
_cell_length_b                   12.4540(2)
_cell_length_c                   21.6161(3)
_cell_measurement_reflns_used    8288
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      73.6570
_cell_measurement_theta_min      4.0660
_cell_volume                     2348.49(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_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_temperature      193(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_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 -17.00   0.50    0.10    --  -42.80 116.00-133.00  150
  2  \w    -64.00 -28.00   0.50    0.42    -- -106.00  37.00 -90.00   72
  3  \w    -67.00 -42.00   0.50    0.42    -- -106.00  57.00-150.00   50
  4  \w    -92.00 -65.00   0.50    0.42    -- -106.00 125.00-180.00   54
  5  \w   -112.00 -32.00   0.50    0.42    -- -106.00 116.00-133.00  160
  6  \w   -109.00 -76.00   0.50    0.10    --  -42.80 165.00  13.00   66
  7  \w   -113.00 -88.00   0.50    0.42    -- -106.00 165.00  13.00   50
  8  \w   -112.00 -32.00   0.50    0.42    -- -106.00 125.00 -30.00  160
  9  \w   -114.00 -75.00   0.50    0.42    -- -106.00 125.00 120.00   78
 10  \w   -116.00 -34.00   0.50    0.42    -- -106.00 125.00  60.00  164
 11  \w   -102.00 -77.00   0.50    0.42    -- -106.00 125.00  30.00   50
 12  \w   -110.00 -42.00   0.50    0.42    -- -106.00 125.00 -90.00  136
 13  \w   -107.00 -76.00   0.50    0.42    -- -106.00  37.00 -90.00   62
 14  \w   -124.00 -98.00   0.50    0.42    -- -106.00  57.00-150.00   52
 15  \w   -177.00 -83.00   0.50    0.42    -- -106.00 -57.00 -90.00  188
 16  \w   -106.00 -80.00   0.50    0.42    -- -106.00 -77.00 -30.00   52
 17  \w   -128.00 -84.00   0.50    0.42    -- -106.00 -99.00  30.00   88
 18  \w   -111.00 -78.00   0.50    0.42    -- -106.00 -77.00  60.00   66
 19  \w   -114.00 -76.00   0.50    0.10    --  -42.80-165.00  -9.00   76
 20  \w     47.00  80.00   0.50    0.10    --   42.80 165.00  13.00   66
 21  \w     72.00 117.00   0.50    0.10    --   42.80 125.00   0.00   90
 22  \w     73.00 101.00   0.50    0.10    --   42.80 125.00 -60.00   56
 23  \w     74.00 114.00   0.50    0.10    --   42.80 125.00 -90.00   80
 24  \w     71.00 112.00   0.50    0.10    --   42.80 125.00 -30.00   82
 25  \w     62.00  87.00   0.50    0.42    --   76.50 165.00  13.00   50
 26  \w     72.00 103.00   0.50    0.10    --   42.80 125.00 120.00   62
 27  \w     89.00 114.00   0.50    0.42    --   76.50 116.00-133.00   50
 28  \w     71.00  96.00   0.50    0.10    --   42.80 125.00-180.00   50
 29  \w    -79.00 -53.00   0.50    0.42    -- -106.00-165.00  -9.00   52
 30  \w   -114.00 -73.00   0.50    0.10    --  -42.80-125.00 -60.00   82
 31  \w   -140.00 -88.00   0.50    0.42    -- -106.00-165.00  -9.00  104
 32  \w   -144.00-113.00   0.50    0.42    -- -106.00-125.00 -90.00   62
 33  \w   -155.00-122.00   0.50    0.42    -- -106.00 -77.00 -30.00   66
 34  \w   -172.00-146.00   0.50    0.42    -- -106.00 -99.00  30.00   52
 35  \w   -170.00-115.00   0.50    0.42    -- -106.00 -77.00  60.00  110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0033054000
_diffrn_orient_matrix_UB_12      -0.1220969000
_diffrn_orient_matrix_UB_13      -0.0115642000
_diffrn_orient_matrix_UB_21      0.1750661000
_diffrn_orient_matrix_UB_22      -0.0047581000
_diffrn_orient_matrix_UB_23      0.0113896000
_diffrn_orient_matrix_UB_31      -0.0227237000
_diffrn_orient_matrix_UB_32      -0.0196042000
_diffrn_orient_matrix_UB_33      0.0694257000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20479
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.110
_diffrn_reflns_theta_min         4.093
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.930
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4706
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0623P)^2^+0.5779P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1157
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4168
_reflns_number_total             4706
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04942b2.cif
_cod_data_source_block           tokura_220228
_cod_database_code               7130851
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C26 H24 O4 P2'
_reflns_odcompleteness_completeness 99.75
_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 Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C23(H23), C8(H8), C15(H15), C21(H21), C5(H5), C11(H11), C7(H7),
 C17(H17), C6(H6), C14(H14), C20(H20), C18(H18), C12(H12), C19(H19), C13(H13)
2.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              79409
_shelx_hkl_checksum              36453
_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 1.397
_oxdiff_exptl_absorpt_empirical_full_min 0.476