Synthesis of chiral supramolecular bisphosphinite palladacycles through hydrogen transfer-promoted self-assembly process.
Vasseur, Alexandre; Membrat, Romain; Palpacelli, Davide; Giorgi, Michel; Nuel, Didier; Giordano, Laurent; Martinez, Alexandre; Chemical communications (Cambridge, England) 54 (2018) 10132–10135; doi:10.1039/c8cc06283h

data_7122115
_publ_section_title
;
 Synthesis of chiral supramolecular bisphosphinite palladacycles through
 hydrogen transfer-promoted self-assembly process.
;
_journal_issue                   72
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10132
_journal_page_last               10135
_journal_paper_doi               10.1039/c8cc06283h
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C37 H38 O4 P2 Pd)'
_chemical_formula_sum            'C74 H76 O8 P4 Pd2'
_chemical_formula_weight         1430.02
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_space_group_name_H-M   'I 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-04-13 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.4520(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.04830(10)
_cell_length_b                   41.2069(4)
_cell_length_c                   22.6837(2)
_cell_measurement_reflns_used    118950
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.1300
_cell_measurement_theta_min      3.7380
_cell_volume                     14702.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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   7.00   1.00    1.00    --  -17.78 -38.00 -60.00   99
  2  \w    -98.00  23.00   1.00    1.00    --  -17.78 -19.00  90.00  121
  3  \w   -105.00 -34.00   1.00    1.00    --  -17.78 178.00 -30.00   71
  4  \w   -107.00 -35.00   1.00    1.00    --  -17.78-178.00 120.00   72
  5  \w    -56.00  42.00   1.00    1.00    --   17.78 -38.00  60.00   98
  6  \w     57.00 107.00   1.00    1.00    --   17.78 178.00  30.00   50
  7  \w     55.00 105.00   1.00    1.00    --   17.78-178.00  60.00   50
  8  \w    -10.00  91.00   1.00    1.00    --   17.78  57.00 -90.00  101
  9  \w     49.00 178.00   1.00   10.00    --  101.41  15.00-180.00  129
 10  \w     28.00 121.00   1.00   10.00    --  101.41-125.00   0.00   93
 11  \w     28.00 127.00   1.00   10.00    --  101.41 -45.00 150.00   99
 12  \w     76.00 174.00   1.00   10.00    --  101.41  45.00-150.00   98
 13  \w     25.00 134.00   1.00   10.00    --  101.41 -77.00 150.00  109
 14  \w     25.00 130.00   1.00   10.00    --  101.41 -30.00   0.00  105
 15  \w     69.00 178.00   1.00   10.00    --  101.41  77.00 120.00  109
 16  \w     19.00 109.00   1.00   10.00    --  101.41 -94.00-180.00   90
 17  \w     94.00 175.00   1.00   10.00    --  101.41 125.00  60.00   81
 18  \w     29.00 130.00   1.00   10.00    --  101.41 -61.00  60.00  101
 19  \w     19.00 109.00   1.00   10.00    --  101.41 -94.00  60.00   90
 20  \w     94.00 175.00   1.00   10.00    --  101.41 125.00 120.00   81
 21  \w    -92.00   7.00   1.00    1.00    --  -17.78 -38.00  30.00   99
 22  \w    -94.00  15.00   1.00    1.00    --  -17.78 -77.00  30.00  109
 23  \w    -94.00  15.00   1.00    1.00    --  -17.78 -77.00 -60.00  109
 24  \w    -94.00  15.00   1.00    1.00    --  -17.78 -77.00-120.00  109
 25  \w    -91.00  10.00   1.00    1.00    --  -17.78 -57.00  30.00  101
 26  \w      1.00  59.00   1.00    1.00    --   17.78 -99.00 150.00   58
 27  \w     49.00 178.00   1.00   10.00    --  101.41  15.00  30.00  129
 28  \w     69.00 178.00   1.00   10.00    --  101.41  77.00 150.00  109
 29  \w     72.00 174.00   1.00   10.00    --  101.41  61.00 -60.00  102
 30  \w     72.00 174.00   1.00   10.00    --  101.41  61.00  30.00  102
 31  \w     72.00 174.00   1.00   10.00    --  101.41  61.00-120.00  102
 32  \w     72.00 174.00   1.00   10.00    --  101.41  61.00  60.00  102
 33  \w     72.00 174.00   1.00   10.00    --  101.41  61.00  90.00  102
 34  \w     72.00 174.00   1.00   10.00    --  101.41  61.00   0.00  102
 35  \w     72.00 174.00   1.00   10.00    --  101.41  61.00-150.00  102
 36  \w     72.00 174.00   1.00   10.00    --  101.41  61.00 -30.00  102
 37  \w     72.00 174.00   1.00   10.00    --  101.41  61.00 120.00  102
 38  \w     72.00 174.00   1.00   10.00    --  101.41  61.00 -90.00  102
 39  \w    -91.00  10.00   1.00    1.00    --  -17.78 -57.00-120.00  101
 40  \w    -98.00  23.00   1.00    1.00    --  -17.78 -19.00  30.00  121
 41  \w    -91.00  10.00   1.00    1.00    --  -17.78 -57.00  90.00  101
 42  \w      1.00  59.00   1.00    1.00    --   17.78 -99.00  60.00   58
 43  \w      1.00  59.00   1.00    1.00    --   17.78 -99.00 -30.00   58
 44  \w      1.00  59.00   1.00    1.00    --   17.78 -99.00-150.00   58
 45  \w     72.00 174.00   1.00   10.00    --  101.41  61.00-180.00  102
 46  \w     69.00 178.00   1.00   10.00    --  101.41  77.00 -90.00  109
 47  \w     69.00 178.00   1.00   10.00    --  101.41  77.00-120.00  109
 48  \w     76.00 174.00   1.00   10.00    --  101.41  45.00  60.00   98
 49  \w     72.00 174.00   1.00   10.00    --  101.41  61.00 150.00  102
 50  \w     69.00 178.00   1.00   10.00    --  101.41  77.00  60.00  109
 51  \w     69.00 178.00   1.00   10.00    --  101.41  77.00-150.00  109
 52  \w     69.00 178.00   1.00   10.00    --  101.41  77.00 -60.00  109
 53  \w     69.00 178.00   1.00   10.00    --  101.41  77.00  90.00  109
 54  \w     69.00 178.00   1.00   10.00    --  101.41  77.00 -30.00  109
 55  \w     69.00 178.00   1.00   10.00    --  101.41  77.00-180.00  109
 56  \w     69.00 178.00   1.00   10.00    --  101.41  77.00   0.00  109
 57  \w    -98.00  23.00   1.00    1.00    --  -17.78 -19.00 -60.00  121
 58  \w    -92.00   7.00   1.00    1.00    --  -17.78 -38.00   0.00   99
 59  \w    -92.00   7.00   1.00    1.00    --  -17.78 -38.00 -90.00   99
 60  \w    -92.00   7.00   1.00    1.00    --  -17.78 -38.00 120.00   99
 61  \w      1.00  59.00   1.00    1.00    --   17.78 -99.00 -90.00   58
 62  \w      1.00  59.00   1.00    1.00    --   17.78 -99.00 120.00   58
 63  \w     69.00 178.00   1.00   10.00    --  101.41  77.00  30.00  109
 64  \w     76.00 174.00   1.00   10.00    --  101.41  45.00 150.00   98
 65  \w     76.00 174.00   1.00   10.00    --  101.41  45.00   0.00   98
 66  \w     76.00 174.00   1.00   10.00    --  101.41  45.00 -30.00   98
 67  \w     76.00 174.00   1.00   10.00    --  101.41  45.00 -90.00   98
 68  \w     76.00 174.00   1.00   10.00    --  101.41  45.00-180.00   98
 69  \w     76.00 174.00   1.00   10.00    --  101.41  45.00 -60.00   98
 70  \w     76.00 174.00   1.00   10.00    --  101.41  45.00  30.00   98
 71  \w     76.00 174.00   1.00   10.00    --  101.41  45.00 120.00   98
 72  \w     76.00 174.00   1.00   10.00    --  101.41  45.00  90.00   98
 73  \w     73.00 178.00   1.00   10.00    --  101.41  30.00-150.00  105
 74  \w     76.00 174.00   1.00   10.00    --  101.41  45.00-120.00   98
 75  \w    -92.00   7.00   1.00    1.00    --  -17.78 -38.00  60.00   99
 76  \w    -98.00  23.00   1.00    1.00    --  -17.78 -19.00  60.00  121
 77  \w    -94.00  15.00   1.00    1.00    --  -17.78 -77.00 -30.00  109
 78  \w      1.00  59.00   1.00    1.00    --   17.78 -99.00   0.00   58
 79  \w    -70.00 106.00   1.00    1.00    --   17.78   0.00-180.00  176
 80  \w     -7.00  92.00   1.00    1.00    --   17.78  38.00-150.00   99
 81  \w     73.00 158.00   1.00   10.00    --  101.41  30.00-120.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0099969000
_diffrn_orient_matrix_UB_12      0.0345744000
_diffrn_orient_matrix_UB_13      -0.0263428000
_diffrn_orient_matrix_UB_21      0.0968857000
_diffrn_orient_matrix_UB_22      0.0020424000
_diffrn_orient_matrix_UB_23      0.0042232000
_diffrn_orient_matrix_UB_31      -0.0106021000
_diffrn_orient_matrix_UB_32      -0.0140858000
_diffrn_orient_matrix_UB_33      -0.0639440000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            323834
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.188
_diffrn_reflns_theta_min         3.751
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.18b (Rigaku Oxford Diffraction, 2015)
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    1.292
_exptl_crystal_description       prism
_exptl_crystal_F_000             5888
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         8.041
_refine_diff_density_min         -0.891
_refine_diff_density_rms         0.184
_refine_ls_abs_structure_details
;
 Flack x determined using 10401 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1561
_refine_ls_number_reflns         28232
_refine_ls_number_restraints     109
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0902
_refine_ls_shift/su_max          0.066
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1609P)^2^+23.9672P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2205
_refine_ls_wR_factor_ref         0.2362
_reflns_Friedel_coverage         0.964
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                24073
_reflns_number_total             28232
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc06283h2.cif
_cod_data_source_block           av89
_cod_depositor_comments
'Adding full bibliography for 7122108--7122115.cif.'
_cod_database_code               7122115
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.456
_shelx_estimated_absorpt_t_min   0.347
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C117 \\sim C118: within 1.7A with sigma of 0.005 and sigma for terminal atoms
of 0.01
C96 \\sim C95: within 1.7A with sigma of 0.001 and sigma for terminal atoms of
0.002
C94 \\sim C95: within 1.7A with sigma of 0.001 and sigma for terminal atoms of
0.002
P8 \\sim C145: within 1.7A with sigma of 0.001 and sigma for terminal atoms of
0.002
C139 \\sim C144: within 1.7A with sigma of 0.001 and sigma for terminal atoms
of 0.002
C139 \\sim C140: within 1.7A with sigma of 0.001 and sigma for terminal atoms
of 0.002
C132 \\sim C133: within 1.7A with sigma of 0.001 and sigma for terminal atoms
of 0.002
3. Rigid body (RIGU) restrains
 C139, C144, C140, C141, C142, C143
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C65, C66, C67, C68, C69, C70
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4.a Riding coordinates:
 O2(H1), O5(H5), O9(H9A), O14(H13A)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C29(H29), C30(H30),
  C31(H31), C32(H32), C33(H33), C40(H40), C41(H41), C43(H43), C44(H44),
 C46(H46), C47(H47), C48(H48), C50(H50), C51(H51), C56(H56), C57(H57), C58(H58),
  C59(H59), C60(H60), C70(H70), C69(H69), C68(H68), C67(H67), C66(H66),
 C77(H77), C78(H78), C80(H80), C81(H81), C83(H83), C84(H84), C85(H85), C87(H87),
  C88(H88), C93(H93), C94(H94), C95(H95), C96(H96), C97(H97), C103(H103),
 C104(H104), C105(H105), C106(H106), C107(H107), C114(H114), C115(H115),
 C117(H117), C118(H118), C120(H120), C121(H121), C122(H122), C124(H124),
 C125(H125), C134(H134), C133(H133), C132(H132), C131(H131), C130(H130),
 C140(H140), C141(H141), C142(H142), C143(H143), C144(H144)
4.c Fitted hexagon refined as free rotating group:
 C65(C70,C69,C68,C67,C66), C129(C134,C133,C132,C131,C130)
4.d Idealised Me refined with riding coordinates:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C35(H35A,H35B,
 H35C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C62(H62A,H62B,H62C), C63(H63A,
 H63B,H63C), C64(H64A,H64B,H64C), C72(H72A,H72B,H72C), C73(H73A,H73B,H73C),
 C74(H74A,H74B,H74C), C99(H99A,H99B,H99C), C100(H10A,H10B,H10C), C101(H10D,H10E,
 H10F), C109(H10G,H10H,H10I), C110(H11A,H11B,H11C), C111(H11D,H11E,H11F),
 C136(H13B,H13C,H13D), C137(H13E,H13F,H13G), C138(H13H,H13I,H13J), C146(H14A,
 H14B,H14C), C147(H14D,H14E,H14F), C148(H14G,H14H,H14I)
;
_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 1.306
_oxdiff_exptl_absorpt_empirical_full_min 0.799