Enantioselective synthesis of <i>P</i>-chiral tertiary phosphine oxides with an ethynyl group <i>via</i> Cu(i)-catalyzed azide-alkyne cycloaddition.
Zhu, Ren-Yi; Chen, Long; Hu, Xiao-Si; Zhou, Feng; Zhou, Jian; Chemical science 11 (2020) 97–106; doi:10.1039/c9sc04938j

data_1552770
_publ_section_title
;
 Enantioselective synthesis of <i>P</i>-chiral tertiary phosphine oxides
 with an ethynyl group <i>via</i> Cu(i)-catalyzed azide-alkyne
 cycloaddition.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              97
_journal_page_last               106
_journal_paper_doi               10.1039/c9sc04938j
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C15 H16 Au Cl P, C H2 Cl2'
_chemical_formula_sum            'C16 H18 Au Cl3 P'
_chemical_formula_weight         544.59
_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             2018-02-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-01 deposited with the CCDC.	2019-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                72.428(3)
_cell_angle_beta                 86.595(3)
_cell_angle_gamma                70.591(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6866(3)
_cell_length_b                   10.7017(4)
_cell_length_c                   11.1556(3)
_cell_measurement_reflns_used    13937
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1140
_cell_measurement_theta_min      4.1550
_cell_volume                     931.50(6)
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.992
_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    -80.00 -49.00   1.00    1.00    --    0.00 -38.00 150.00   31
  2  \w    -84.00 -59.00   1.00    1.00    --    0.00 -38.00 -60.00   25
  3  \w    -17.00  53.00   1.00    1.00    --    0.00  57.00-180.00   70
  4  \w    -24.00   2.00   1.00    1.00    --    0.00  19.00  60.00   26
  5  \w     13.00  43.00   1.00    1.00    --    0.00  82.00 -90.00   30
  6  \w    -32.00  -1.00   1.00    1.00    --    0.00 -38.00 150.00   31
  7  \w    -31.00  15.00   1.00    1.00    --    0.00  82.00  90.00   46
  8  \w    -87.00   3.00   1.00    1.00    --    0.00 -38.00-120.00   90
  9  \w     10.00  67.00   1.00    1.00    --    0.00  19.00  60.00   57
 10  \w     31.00  67.00   1.00    1.00    --    0.00  82.00  90.00   36
 11  \w    -54.00  15.00   1.00    1.00    --    0.00 -38.00 -60.00   69
 12  \w    -26.00   9.00   1.00    1.00    --    0.00  82.00 -90.00   35
 13  \w     65.00  90.00   1.00    2.00    --   95.80  77.00-150.00   25
 14  \w    160.00 185.00   1.00    2.00    --   95.80  82.00 150.00   25
 15  \w    113.00 175.00   1.00    2.00    --   95.80  71.00  80.32   62
 16  \w     64.00  90.00   1.00    2.00    --   95.80  82.00 150.00   26
 17  \w    160.00 185.00   1.00    2.00    --   95.80  77.00   0.00   25
 18  \w     69.00 100.00   1.00    2.00    --   95.80  71.00  80.32   31
 19  \w     65.00  94.00   1.00    2.00    --   95.80  77.00-116.42   29
 20  \w     59.00 127.00   1.00    2.00    --   95.80 -82.00-180.00   68
 21  \w    113.00 185.00   1.00    2.00    --   95.80  82.00 -90.00   72
 22  \w     65.00  90.00   1.00    2.00    --   95.80  77.00   0.00   25
 23  \w     64.00  90.00   1.00    2.00    --   95.80  82.00-180.00   26
 24  \w     64.00  89.00   1.00    2.00    --   95.80  82.00 120.00   25
 25  \w    117.00 183.00   1.00    2.00    --   95.80  82.00 120.00   66
 26  \w     65.00  90.00   1.00    2.00    --   95.80  77.00  60.00   25
 27  \w    116.00 184.00   1.00    2.00    --   95.80  77.00  60.00   68
 28  \w     65.00  91.00   1.00    2.00    --   95.80  77.00-180.00   26
 29  \w     64.00  96.00   1.00    2.00    --   95.80  82.00 -90.00   32
 30  \w     65.00 101.00   1.00    2.00    --   95.80  77.00  30.00   36
 31  \w     92.00 128.00   1.00    2.00    --   95.80 -82.00 -30.00   36
 32  \w     38.00 123.00   1.00    2.00    --   95.80 -82.00 -90.00   85
 33  \w     71.00 106.00   1.00    2.00    --   95.80  61.00 -81.88   35
 34  \w     43.00  76.00   1.00    2.00    --   95.80 -82.00 -30.00   33
 35  \w    148.00 174.00   1.00    2.00    --   95.80  77.00 150.00   26
 36  \w     65.00  90.00   1.00    2.00    --   95.80  77.00 150.00   25
 37  \w    129.00 184.00   1.00    2.00    --   95.80  82.00 -30.00   55
 38  \w    129.00 179.00   1.00    2.00    --   95.80  70.00 -56.54   50
 39  \w     63.00  94.00   1.00    2.00    --   95.80  82.00-150.00   31
 40  \w     38.00 127.00   1.00    2.00    --   95.80 -82.00 120.00   89
 41  \w     63.00  97.00   1.00    2.00    --   95.80  82.00   0.00   34
 42  \w     63.00  98.00   1.00    2.00    --   95.80  82.00  90.00   35
 43  \w     75.00 150.00   1.00    2.00    --   95.80  45.00-180.00   75
 44  \w     76.00 108.00   1.00    2.00    --   95.80  45.00-150.00   32
 45  \w    127.00 184.00   1.00    2.00    --   95.80  45.00-150.00   57
 46  \w     75.00 184.00   1.00    2.00    --   95.80  45.00-120.00  109
 47  \w     75.00 106.00   1.00    2.00    --   95.80  45.00 -30.00   31
 48  \w    136.00 162.00   1.00    2.00    --   95.80  45.00 -30.00   26
 49  \w     80.00 113.00   1.00    2.00    --   95.80  45.00  30.00   33
 50  \w    130.00 184.00   1.00    2.00    --   95.80  45.00  30.00   54
 51  \w     65.00  91.00   1.00    2.00    --   95.80  82.00  30.00   26
 52  \w     72.00  97.00   1.00    2.00    --   95.80  61.00   0.00   25
 53  \w     75.00 104.00   1.00    2.00    --   95.80  45.00   0.00   29
 54  \w    139.00 184.00   1.00    2.00    --   95.80  45.00   0.00   45
 55  \w     76.00 106.00   1.00    2.00    --   95.80  45.00  60.00   30
 56  \w    123.00 149.00   1.00    2.00    --   95.80  45.00  60.00   26
 57  \w     63.00  94.00   1.00    2.00    --   95.80  82.00 -60.00   31
 58  \w     63.00  89.00   1.00    2.00    --   95.80  82.00 -30.00   26
 59  \w     65.00  90.00   1.00    2.00    --   95.80  77.00 -90.00   25
 60  \w     76.00 110.00   1.00    2.00    --   95.80  45.00 150.00   34
 61  \w     75.00 100.00   1.00    2.00    --   95.80  45.00  90.00   25
 62  \w     65.00  91.00   1.00    2.00    --   95.80  77.00  90.00   26
 63  \w    151.00 176.00   1.00    2.00    --   95.80  77.00-150.00   25
 64  \w     68.00  94.00   1.00    2.00    --   95.80  70.00 -56.54   26
 65  \w    129.00 154.00   1.00    2.00    --   95.80  45.00 150.00   25
 66  \w     74.00 182.00   1.00    2.00    --   95.80  48.00 155.40  108
 67  \w    127.00 176.00   1.00    2.00    --   95.80  34.00 -75.96   49
 68  \w     61.00 103.00   1.00    2.00    --   95.80 -82.00  60.00   42
 69  \w     76.00 102.00   1.00    2.00    --   95.80  34.00 -75.96   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      -0.0118526000
_diffrn_orient_matrix_UB_12      0.0564606000
_diffrn_orient_matrix_UB_13      -0.1447779000
_diffrn_orient_matrix_UB_21      0.0694489000
_diffrn_orient_matrix_UB_22      -0.1495539000
_diffrn_orient_matrix_UB_23      -0.0081460000
_diffrn_orient_matrix_UB_31      -0.1745487000
_diffrn_orient_matrix_UB_32      -0.0063439000
_diffrn_orient_matrix_UB_33      -0.0005292000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1194
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17430
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.048
_diffrn_reflns_theta_max         67.048
_diffrn_reflns_theta_min         4.161
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    19.528
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14142
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.942
_exptl_crystal_description       block
_exptl_crystal_F_000             518
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_refine_diff_density_max         2.271
_refine_diff_density_min         -2.080
_refine_diff_density_rms         0.209
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3313
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0570
_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^)+(0.1100P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1508
_refine_ls_wR_factor_ref         0.1531
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3039
_reflns_number_total             3313
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc04938j3.cif
_cod_data_source_block           exp_248
_cod_depositor_comments
;Adding full bibliography for 1552766--1552772.cif.

 Adding full bibliography for 1552766--1552772.cif.
;
_cod_database_code               1552770
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.342
_shelx_estimated_absorpt_t_min   0.065
_reflns_odcompleteness_completeness 99.46
_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:
 C13(H13A,H13B), C14(H14A,H14B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C12(H12), C11(H11), C2(H2), C10(H10), C9(H9), C5(H5), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              10612
_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 9.756
_oxdiff_exptl_absorpt_empirical_full_min 0.224