Co-catalysis over a tri-functional ligand modified Pd-catalyst for hydroxycarbonylation of terminal alkynes towards α,β-unsaturated carboxylic acids
Yang, Da; Liu, Huan; Liu, Lei; Guo, Wen-Di; Lu, Yong; Liu, Ye; Green Chemistry 21 (2019) 5336–; doi:10.1039/C9GC01887E

data_7233413
_publ_section_title
;
 Co-catalysis over a tri-functional ligand modified Pd-catalyst for
 hydroxycarbonylation of terminal alkynes towards \a,\b-unsaturated
 carboxylic acids
;
_journal_issue                   19
_journal_name_full               'Green Chemistry'
_journal_page_first              5336
_journal_paper_doi               10.1039/C9GC01887E
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C42 H38 Cl2 O4 P2 Pd S'
_chemical_formula_sum            'C42 H38 Cl2 O4 P2 Pd S'
_chemical_formula_weight         878.02
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-04 deposited with the CCDC.    2019-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.6360(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.7161(2)
_cell_length_b                   13.98050(10)
_cell_length_c                   19.1927(2)
_cell_measurement_reflns_used    40984
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1770
_cell_measurement_theta_min      4.1150
_cell_volume                     4319.34(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_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    -86.00 -53.00   1.00    3.00    --    0.00 -46.00  53.00   33
  2  \w    -20.00  42.00   1.00    3.00    --    0.00  46.00-156.00   62
  3  \w     76.00 184.00   1.00    3.00    --   95.80  46.00-156.00  108
  4  \w     41.00  67.00   1.00    3.00    --   95.80 -46.00  53.00   26
  5  \w    -17.00  89.00   1.00    3.00    --    0.00  77.00 120.00  106
  6  \w    -17.00  89.00   1.00    3.00    --    0.00  38.00 -90.00  106
  7  \w    -78.00 -39.00   1.00    3.00    --    0.00 -19.00 150.00   39
  8  \w    -17.00  28.00   1.00    3.00    --    0.00  38.00 -30.00   45
  9  \w    -19.00  10.00   1.00    3.00    --    0.00  38.00  30.00   29
 10  \w     14.00  84.00   1.00    3.00    --    0.00  57.00  90.00   70
 11  \w     28.00  85.00   1.00    3.00    --    0.00  38.00   0.00   57
 12  \w     57.00  84.00   1.00    3.00    --    0.00  38.00  90.00   27
 13  \w     33.00  83.00   1.00    3.00    --    0.00  38.00  30.00   50
 14  \w    -22.00  51.00   1.00    3.00    --    0.00  82.00  30.00   73
 15  \w     38.00  89.00   1.00    3.00    --    0.00  38.00 -30.00   51
 16  \w    -15.00  11.00   1.00    3.00    --    0.00  38.00   0.00   26
 17  \w    -18.00  53.00   1.00    3.00    --    0.00  38.00  90.00   71
 18  \w    -31.00  23.00   1.00    3.00    --    0.00 -19.00 150.00   54
 19  \w     63.00 105.00   1.00    3.00    --   95.80  82.00  30.00   42
 20  \w     75.00 101.00   1.00    3.00    --   95.80  45.00  90.00   26
 21  \w    140.00 166.00   1.00    3.00    --   95.80  68.00-154.17   26
 22  \w     68.00  94.00   1.00    3.00    --   95.80  68.00-154.17   26
 23  \w    137.00 175.00   1.00    3.00    --   95.80  61.00 -30.00   38
 24  \w     65.00  91.00   1.00    3.00    --   95.80  77.00 150.00   26
 25  \w     63.00  89.00   1.00    3.00    --   95.80  81.00 -16.86   26
 26  \w     65.00  91.00   1.00    3.00    --   95.80  77.00-180.00   26
 27  \w     63.00  89.00   1.00    3.00    --   95.80  81.00-107.25   26
 28  \w    103.00 182.00   1.00    3.00    --   95.80  81.00-107.25   79
 29  \w     65.00 108.00   1.00    3.00    --   95.80  77.00   0.00   43
 30  \w     68.00 138.00   1.00    3.00    --   95.80  68.00 -53.09   70
 31  \w     66.00  93.00   1.00    3.00    --   95.80  75.00 -60.59   27
 32  \w     68.00  95.00   1.00    3.00    --   95.80  68.00 149.82   27
 33  \w     65.00 142.00   1.00    3.00    --   95.80  77.00 -90.00   77
 34  \w     64.00  89.00   1.00    3.00    --   95.80  82.00  90.00   25
 35  \w     72.00 135.00   1.00    3.00    --   95.80  61.00 -30.00   63
 36  \w     63.00  89.00   1.00    3.00    --   95.80  82.00-150.00   26
 37  \w     65.00  91.00   1.00    3.00    --   95.80  77.00 -30.00   26
 38  \w    145.00 178.00   1.00    3.00    --   95.80  82.00  77.33   33
 39  \w     89.00 127.00   1.00    3.00    --   95.80 -82.00  60.00   38
 40  \w     63.00  89.00   1.00    3.00    --   95.80  81.00  70.42   26
 41  \w     65.00 119.00   1.00    3.00    --   95.80  77.00 120.00   54
 42  \w     64.00  90.00   1.00    3.00    --   95.80  79.00 106.46   26
 43  \w    135.00 162.00   1.00    3.00    --   95.80  81.00  70.42   27
 44  \w     63.00 184.00   1.00    3.00    --   95.80  82.00-120.00  121
 45  \w     63.00  89.00   1.00    3.00    --   95.80  82.00 -60.00   26
 46  \w     37.00 128.00   1.00    3.00    --   95.80 -82.00 -30.00   91
 47  \w     63.00  90.00   1.00    3.00    --   95.80  82.00 -30.00   27
 48  \w     69.00 185.00   1.00    3.00    --   95.80  66.00 -24.43  116
 49  \w     65.00 101.00   1.00    3.00    --   95.80  78.00-136.76   36
 50  \w     67.00  93.00   1.00    3.00    --   95.80  72.00 -68.60   26
 51  \w     63.00  89.00   1.00    3.00    --   95.80  82.00  77.33   26
 52  \w     63.00  89.00   1.00    3.00    --   95.80  82.00 -90.00   26
 53  \w     63.00  89.00   1.00    3.00    --   95.80  82.00   0.00   26
 54  \w     76.00 185.00   1.00    3.00    --   95.80  48.00  92.59  109
 55  \w     71.00 176.00   1.00    3.00    --   95.80  61.00 120.00  105
 56  \w     65.00  91.00   1.00    3.00    --   95.80  77.00  90.00   26
 57  \w     63.00  89.00   1.00    3.00    --   95.80  82.00-180.00   26
 58  \w     76.00 139.00   1.00    3.00    --   95.80  36.00  38.65   63
 59  \w     93.00 119.00   1.00    3.00    --   95.80  80.00-158.94   26
 60  \w     64.00  90.00   1.00    3.00    --   95.80  80.00-158.94   26
 61  \w     14.00 127.00   1.00    3.00    --   95.80 -82.00 150.00  113
 62  \w     76.00 102.00   1.00    3.00    --   95.80  45.00 -90.00   26
 63  \w    142.00 185.00   1.00    3.00    --   95.80  76.00  23.21   43
 64  \w     76.00 178.00   1.00    3.00    --   95.80  31.00  71.23  102
 65  \w     68.00  94.00   1.00    3.00    --   95.80  68.00 170.20   26
 66  \w    109.00 185.00   1.00    3.00    --   95.80  68.00 170.20   76
 67  \w     19.00 116.00   1.00    3.00    --   95.80 -82.00  28.81   97
 68  \w     10.00 126.00   1.00    3.00    --   95.80 -77.00-180.00  116
 69  \w     65.00  95.00   1.00    3.00    --   95.80  76.00  23.21   30
 70  \w     65.00  91.00   1.00    3.00    --   95.80  77.00-120.00   26
 71  \w     64.00  90.00   1.00    3.00    --   95.80  79.00 124.99   26
 72  \w    139.00 184.00   1.00    3.00    --   95.80  79.00 124.99   45
 73  \w      8.00  66.00   1.00    3.00    --   95.80 -82.00  60.00   58
 74  \w    160.00 185.00   1.00    3.00    --   95.80  82.00  60.00   25
 75  \w     12.00 128.00   1.00    3.00    --   95.80 -82.00-120.00  116
 76  \w     63.00  89.00   1.00    3.00    --   95.80  82.00  60.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0761459000
_diffrn_orient_matrix_UB_12      0.0142196000
_diffrn_orient_matrix_UB_13      0.0295859000
_diffrn_orient_matrix_UB_21      -0.0383743000
_diffrn_orient_matrix_UB_22      -0.0929066000
_diffrn_orient_matrix_UB_23      -0.0375884000
_diffrn_orient_matrix_UB_31      0.0433641000
_diffrn_orient_matrix_UB_32      -0.0574961000
_diffrn_orient_matrix_UB_33      0.0683222000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0962
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            117643
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.610
_diffrn_reflns_theta_min         3.965
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.059
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       block
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         1.052
_refine_diff_density_min         -1.172
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         8798
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0563P)^2^+11.8670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1177
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8163
_reflns_number_total             8798
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc01887e2.cif
_cod_data_source_block           exp_674
_cod_depositor_comments          'Adding full bibliography for 7233413.cif.'
_cod_database_code               7233413
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.349
_shelx_estimated_absorpt_t_min   0.219
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
  C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C33(H33), C34(H34),
 C35(H35), C36(H36), C37(H37)
2.c Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C42(H42A,H42B,H42C)
;
_shelx_res_checksum              32321
_shelx_fab_checksum              18602
_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 5.208
_oxdiff_exptl_absorpt_empirical_full_min 0.325