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_1552769
_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_absolute_configuration ad
_chemical_formula_moiety         'C24 H32 N O2 P S'
_chemical_formula_sum            'C24 H32 N O2 P S'
_chemical_formula_weight         429.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-05 deposited with the CCDC.	2019-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.0600(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.07450(10)
_cell_length_b                   19.8094(2)
_cell_length_c                   9.96830(10)
_cell_measurement_reflns_used    14448
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      74.2080
_cell_measurement_theta_min      4.4400
_cell_volume                     1187.66(3)
_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(11)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_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    -27.00  60.00   1.00    3.00    --    0.00  68.00 119.00   87
  2  \w     52.00 122.00   1.00    3.00    --   95.80 -68.00 -13.00   70
  3  \w    148.00 181.00   1.00    3.00    --   95.80  68.00 119.00   33
  4  \w     68.00 117.00   1.00    3.00    --   95.80  68.00 119.00   49
  5  \w    -65.00 -39.00   1.00    3.00    --    0.00 -57.00-120.00   26
  6  \w    -29.00   5.00   1.00    3.00    --    0.00 -38.00 120.00   34
  7  \w     -3.00  61.00   1.00    3.00    --    0.00  77.00 -60.00   64
  8  \w     -7.00  27.00   1.00    3.00    --    0.00 -68.00 -13.00   34
  9  \w    -29.00   6.00   1.00    3.00    --    0.00 -38.00   0.00   35
 10  \w    -31.00  51.00   1.00    3.00    --    0.00  82.00-180.00   82
 11  \w    -69.00 -44.00   1.00    3.00    --    0.00 -38.00 120.00   25
 12  \w    -18.00  89.00   1.00    3.00    --    0.00  38.00  30.00  107
 13  \w    -15.00  23.00   1.00    3.00    --    0.00 -57.00-120.00   38
 14  \w     55.00  81.00   1.00    3.00    --    0.00  82.00-180.00   26
 15  \w    -67.00  18.00   1.00    3.00    --    0.00 -38.00  60.00   85
 16  \w    -87.00 -44.00   1.00    3.00    --    0.00 -38.00   0.00   43
 17  \w     73.00 185.00   1.00    3.00    --   95.80  52.00  69.30  112
 18  \w     65.00  91.00   1.00    3.00    --   95.80  77.00  90.00   26
 19  \w    127.00 153.00   1.00    3.00    --   95.80  82.00  30.00   26
 20  \w    119.00 170.00   1.00    3.00    --   95.80  79.00  -5.32   51
 21  \w     64.00  90.00   1.00    3.00    --   95.80  79.00  -5.32   26
 22  \w     66.00  92.00   1.00    3.00    --   95.80  82.00  30.00   26
 23  \w    149.00 175.00   1.00    3.00    --   95.80  82.00  60.00   26
 24  \w      6.00 127.00   1.00    3.00    --   95.80 -82.00 -30.00  121
 25  \w     64.00  89.00   1.00    3.00    --   95.80  79.00 -44.37   25
 26  \w      7.00 127.00   1.00    3.00    --   95.80 -82.00-120.00  120
 27  \w     65.00  90.00   1.00    3.00    --   95.80  77.00  60.00   25
 28  \w     71.00 109.00   1.00    3.00    --   95.80  61.00 -60.00   38
 29  \w    115.00 140.00   1.00    3.00    --   95.80  61.00 -60.00   25
 30  \w     69.00 123.00   1.00    3.00    --   95.80  69.00-149.98   54
 31  \w     67.00 181.00   1.00    3.00    --   95.80  73.00 -95.36  114
 32  \w     24.00 125.00   1.00    3.00    --   95.80 -82.00 150.00  101
 33  \w     65.00  90.00   1.00    3.00    --   95.80  77.00-120.00   25
 34  \w     71.00 116.00   1.00    3.00    --   95.80  58.00  46.37   45
 35  \w     76.00 185.00   1.00    3.00    --   95.80  45.00  30.00  109
 36  \w     63.00  99.00   1.00    3.00    --   95.80  82.00 150.00   36
 37  \w    119.00 153.00   1.00    3.00    --   95.80  45.00-180.00   34
 38  \w    124.00 181.00   1.00    3.00    --   95.80  68.00-174.81   57
 39  \w     65.00  90.00   1.00    3.00    --   95.80  77.00 -90.00   25
 40  \w     68.00  94.00   1.00    3.00    --   95.80  68.00-174.81   26
 41  \w    139.00 170.00   1.00    3.00    --   95.80  62.00 -46.08   31
 42  \w     63.00  88.00   1.00    3.00    --   95.80  82.00  90.00   25
 43  \w     63.00  88.00   1.00    3.00    --   95.80  82.00-150.00   25
 44  \w    140.00 166.00   1.00    3.00    --   95.80  61.00 150.00   26
 45  \w     71.00 105.00   1.00    3.00    --   95.80  62.00 -46.08   34
 46  \w     71.00  97.00   1.00    3.00    --   95.80  61.00   0.00   26
 47  \w     65.00  90.00   1.00    3.00    --   95.80  77.00 -60.00   25
 48  \w    109.00 185.00   1.00    3.00    --   95.80  77.00 -60.00   76
 49  \w     63.00  89.00   1.00    3.00    --   95.80  82.00-180.00   26
 50  \w     71.00  96.00   1.00    3.00    --   95.80  61.00  90.00   25
 51  \w    140.00 181.00   1.00    3.00    --   95.80  45.00 120.00   41
 52  \w     65.00  90.00   1.00    3.00    --   95.80  77.00-150.00   25
 53  \w     65.00  95.00   1.00    3.00    --   95.80  77.00 -30.00   30
 54  \w     75.00 130.00   1.00    3.00    --   95.80  45.00 120.00   55
 55  \w     75.00 101.00   1.00    3.00    --   95.80  45.00-150.00   26
 56  \w    132.00 183.00   1.00    3.00    --   95.80  45.00-150.00   51
 57  \w     75.00 114.00   1.00    3.00    --   95.80  45.00  90.00   39
 58  \w    117.00 143.00   1.00    3.00    --   95.80  45.00  90.00   26
 59  \w     70.00 116.00   1.00    3.00    --   95.80  63.00-111.14   46
 60  \w    136.00 175.00   1.00    3.00    --   95.80  63.00-111.14   39
 61  \w     56.00 124.00   1.00    3.00    --   95.80 -82.00  60.00   68
 62  \w     65.00  90.00   1.00    3.00    --   95.80  77.00 120.00   25
 63  \w     71.00  97.00   1.00    3.00    --   95.80  61.00 150.00   26
 64  \w     78.00 104.00   1.00    3.00    --   95.80  45.00-180.00   26
 65  \w     71.00  96.00   1.00    3.00    --   95.80  61.00  30.00   25
 66  \w     63.00  88.00   1.00    3.00    --   95.80  82.00  60.00   25
;
_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      0.1348183000
_diffrn_orient_matrix_UB_12      -0.0361557000
_diffrn_orient_matrix_UB_13      0.1215217000
_diffrn_orient_matrix_UB_21      0.0978873000
_diffrn_orient_matrix_UB_22      -0.0480560000
_diffrn_orient_matrix_UB_23      -0.0977687000
_diffrn_orient_matrix_UB_31      0.1946298000
_diffrn_orient_matrix_UB_32      0.0492827000
_diffrn_orient_matrix_UB_33      -0.0061647000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            26423
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.404
_diffrn_reflns_theta_min         4.480
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.989
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29937
_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    1.201
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 2082 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4775
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0311
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0396P)^2^+0.2049P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0753
_reflns_Friedel_coverage         0.913
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                4602
_reflns_number_total             4775
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc04938j3.cif
_cod_data_source_block           exp_816
_cod_depositor_comments
;Adding full bibliography for 1552766--1552772.cif.

 Adding full bibliography for 1552766--1552772.cif.
;
_cod_database_code               1552769
_shelx_shelxl_version_number     2016/6
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C18(H18a,H18b,H18c), C19(H19a,H19b,H19c), C20(H20a,H20b,
 H20c), C22(H22a,H22b,H22c), C23(H23a,H23b,H23c), C24(H24a,H24b,H24c)
;
_shelx_res_checksum              90581
_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 3.618
_oxdiff_exptl_absorpt_empirical_full_min 0.488