Palladium-Catalyzed Highly Regioselective Hydrocarboxylation of Alkynes with Carbon Dioxide
Xiong, Wenfang; Shi, Fuxing; Cheng, Ruixiang; Zhu, Baiyao; Wang, Lu; Chen, Pengquan; Lou, Hongming; Wu, Wanqing; Qi, Chaorong; Lei, Ming; Jiang, Huanfeng; ACS Catalysis  (2020) 7968–; doi:10.1021/acscatal.0c01687

data_4517838
_publ_section_title
;
 Palladium-Catalyzed Highly Regioselective Hydrocarboxylation of Alkynes
 with Carbon Dioxide
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              7968
_journal_paper_doi               10.1021/acscatal.0c01687
_journal_year                    2020
_chemical_formula_moiety         'C61 H46 O P2 Pd'
_chemical_formula_sum            'C61 H46 O P2 Pd'
_chemical_formula_weight         963.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-11
_audit_creation_method
;
Olex2 1.3-alpha
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.351(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.3983(5)
_cell_length_b                   13.9556(3)
_cell_length_c                   20.8118(6)
_cell_measurement_reflns_used    6117
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.6480
_cell_measurement_theta_min      2.7510
_cell_volume                     5041.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.970
_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    -66.00 -24.00   1.00    1.00    --  -40.98  38.00 150.00   42
  2  \w   -115.00 -16.00   1.00    1.00    --  -40.98 -38.00 -30.00   99
  3  \w     26.00  53.00   1.00    1.00    --   40.98-125.00-180.00   27
  4  \w     26.00  62.00   1.00    1.00    --   40.98-125.00 -60.00   36
  5  \w     31.00 125.00   1.00    1.20    --  106.95 -77.00   0.00   94
  6  \w     71.00 100.00   1.00    1.20    --  106.95 -95.00-120.00   29
  7  \w     44.00 159.00   1.00    1.20    --  106.95 -15.00 -90.00  115
  8  \w     78.00 175.00   1.00    1.20    --  106.95  61.00 -60.00   97
  9  \w     76.00 132.00   1.00    1.20    --  106.95 -61.00 150.00   56
 10  \w     39.00 103.00   1.00    1.20    --  106.95 -95.00 150.00   64
 11  \w    -75.00 -38.00   1.00    1.00    --  -40.98 125.00-180.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0680932000
_diffrn_orient_matrix_UB_12      -0.0639534000
_diffrn_orient_matrix_UB_13      0.0003922000
_diffrn_orient_matrix_UB_21      0.0287814000
_diffrn_orient_matrix_UB_22      -0.0795939000
_diffrn_orient_matrix_UB_23      -0.0369172000
_diffrn_orient_matrix_UB_31      0.0490837000
_diffrn_orient_matrix_UB_32      -0.0420742000
_diffrn_orient_matrix_UB_33      0.0692092000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20529
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.695
_diffrn_reflns_theta_min         3.886
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.870
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     586
_refine_ls_number_reflns         9887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0409P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1110
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7173
_reflns_number_total             9887
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c01687_si_003.cif
_cod_data_source_block           xwf-1210-2
_cod_database_code               4517838
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C55(H55), C54(H54)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C22(H22), C16(H16), C21(H21), C4(H4), C51(H51), C2(H2), C6(H6),
 C12(H12), C52(H52), C15(H15), C41(H41), C28(H28), C35(H35), C25(H25), C26(H26),
  C23(H23), C3(H3), C14(H14), C40(H40), C5(H5), C46(H46), C13(H13), C24(H24),
 C36(H36), C32(H32), C33(H33), C61(H61), C43(H43), C50(H50), C37(H37), C48(H48),
  C29(H29), C42(H42), C60(H60), C47(H47), C49(H49), C44(H44), C30(H30),
 C59(H59), C57(H57), C31(H31), C38(H38), C58(H58)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              61777
_shelx_hkl_checksum              72245
_shelx_fab_checksum              78195
_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 2.096
_oxdiff_exptl_absorpt_empirical_full_min 0.696