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_1552768
_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         'C19 H23 O3 P'
_chemical_formula_sum            'C19 H23 O3 P'
_chemical_formula_weight         330.34
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-28
_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                 107.963(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3114(2)
_cell_length_b                   10.1411(2)
_cell_length_c                   10.8128(2)
_cell_measurement_reflns_used    24096
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1870
_cell_measurement_theta_min      4.0630
_cell_volume                     866.95(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(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_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    -17.00  21.00   1.00    1.00    --    0.00  82.00  90.00   38
  2  \w     25.00  89.00   1.00    1.00    --    0.00  77.00 -60.00   64
  3  \w    -22.00  52.00   1.00    1.00    --    0.00  57.00-120.00   74
  4  \w     45.00  88.00   1.00    1.00    --    0.00  19.00  30.00   43
  5  \w    -23.00  52.00   1.00    1.00    --    0.00  19.00-150.00   75
  6  \w    -21.00  19.00   1.00    1.00    --    0.00  19.00  30.00   40
  7  \w    -22.00  63.00   1.00    1.00    --    0.00  19.00 -90.00   85
  8  \w    -18.00  62.00   1.00    1.00    --    0.00  38.00 -30.00   80
  9  \w    -19.00  59.00   1.00    1.00    --    0.00  38.00  90.00   78
 10  \w     26.00  84.00   1.00    1.00    --    0.00  82.00  90.00   58
 11  \w     60.00  89.00   1.00    1.00    --    0.00  57.00-120.00   29
 12  \w     10.00  59.00   1.00    1.00    --    0.00  38.00 150.00   49
 13  \w     65.00  96.00   1.00    1.00    --   95.80  79.00  71.70   31
 14  \w    134.00 160.00   1.00    1.00    --   95.80  50.00  24.02   26
 15  \w     64.00  90.00   1.00    1.00    --   95.80  80.00  47.18   26
 16  \w     74.00 100.00   1.00    1.00    --   95.80  50.00  24.02   26
 17  \w    108.00 180.00   1.00    1.00    --   95.80  68.00-112.96   72
 18  \w     68.00 137.00   1.00    1.00    --   95.80  68.00 126.44   69
 19  \w     69.00 107.00   1.00    1.00    --   95.80  66.00 -57.14   38
 20  \w     72.00 184.00   1.00    1.00    --   95.80  61.00 -30.00  112
 21  \w    132.00 157.00   1.00    1.00    --   95.80  61.00-120.00   25
 22  \w     68.00  98.00   1.00    1.00    --   95.80  68.00-112.96   30
 23  \w     64.00  90.00   1.00    1.00    --   95.80  82.00  90.00   26
 24  \w     71.00 106.00   1.00    1.00    --   95.80  61.00 -90.00   35
 25  \w    129.00 155.00   1.00    1.00    --   95.80  61.00 -90.00   26
 26  \w     66.00  92.00   1.00    1.00    --   95.80  77.00-180.00   26
 27  \w    123.00 185.00   1.00    1.00    --   95.80  77.00-180.00   62
 28  \w     14.00  39.00   1.00    1.00    --   95.80 -82.00 120.00   25
 29  \w     45.00  73.00   1.00    1.00    --   95.80 -82.00 120.00   28
 30  \w     79.00 128.00   1.00    1.00    --   95.80 -82.00 120.00   49
 31  \w     71.00 104.00   1.00    1.00    --   95.80  61.00-120.00   33
 32  \w     70.00 127.00   1.00    1.00    --   95.80 -82.00 -30.00   57
 33  \w     63.00 184.00   1.00    1.00    --   95.80  82.00 128.92  121
 34  \w    160.00 185.00   1.00    1.00    --   95.80  66.00 -57.14   25
 35  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-150.00   25
 36  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -30.00   26
 37  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -60.00   26
 38  \w    144.00 170.00   1.00    1.00    --   95.80  77.00 150.00   26
 39  \w     65.00  91.00   1.00    1.00    --   95.80  77.00   0.00   26
 40  \w     63.00  89.00   1.00    1.00    --   95.80  82.00-120.00   26
 41  \w     57.00 127.00   1.00    1.00    --   95.80 -82.00  60.00   70
 42  \w     68.00  97.00   1.00    1.00    --   95.80  69.00-177.03   29
 43  \w     65.00 185.00   1.00    1.00    --   95.80  77.00  90.00  120
 44  \w    141.00 167.00   1.00    1.00    --   95.80  78.00 -80.17   26
 45  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 46  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  30.00   25
 47  \w     78.00 181.00   1.00    1.00    --   95.80  45.00 -60.00  103
 48  \w     66.00  91.00   1.00    1.00    --   95.80  77.00 120.00   25
 49  \w    146.00 171.00   1.00    1.00    --   95.80  77.00 120.00   25
 50  \w     66.00  92.00   1.00    1.00    --   95.80  82.00   0.00   26
 51  \w    115.00 184.00   1.00    1.00    --   95.80  82.00   0.00   69
 52  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  60.00   25
 53  \w      8.00  34.00   1.00    1.00    --   95.80 -82.00-150.00   26
 54  \w     47.00  72.00   1.00    1.00    --   95.80 -82.00-150.00   25
 55  \w     81.00 128.00   1.00    1.00    --   95.80 -82.00-150.00   47
 56  \w     68.00  94.00   1.00    1.00    --   95.80  82.00-150.00   26
 57  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 150.00   26
 58  \w     78.00 103.00   1.00    1.00    --   95.80  45.00   0.00   25
 59  \w    137.00 162.00   1.00    1.00    --   95.80  45.00   0.00   25
 60  \w     68.00 185.00   1.00    1.00    --   95.80  69.00-154.81  117
 61  \w     96.00 127.00   1.00    1.00    --   95.80 -82.00  30.00   31
 62  \w     65.00 140.00   1.00    1.00    --   95.80  77.00 150.00   75
 63  \w      6.00 118.00   1.00    1.00    --   95.80 -77.00 -90.00  112
 64  \w     65.00  90.00   1.00    1.00    --   95.80  78.00 -80.17   25
 65  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -30.00   26
 66  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 67  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 68  \w     79.00 118.00   1.00    1.00    --   95.80  30.00  30.00   39
 69  \w     75.00 137.00   1.00    1.00    --   95.80  45.00  90.00   62
 70  \w    129.00 169.00   1.00    1.00    --   95.80  79.00  71.70   40
 71  \w    121.00 167.00   1.00    1.00    --   95.80  80.00  47.18   46
 72  \w    122.00 147.00   1.00    1.00    --   95.80  66.00 -57.14   25
 73  \w     71.00 104.00   1.00    1.00    --   95.80  61.00  24.72   33
 74  \w     74.00 100.00   1.00    1.00    --   95.80  52.00  52.55   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      -0.1213467000
_diffrn_orient_matrix_UB_12      0.0462152000
_diffrn_orient_matrix_UB_13      0.0149931000
_diffrn_orient_matrix_UB_21      -0.0609873000
_diffrn_orient_matrix_UB_22      -0.0120368000
_diffrn_orient_matrix_UB_23      -0.1009503000
_diffrn_orient_matrix_UB_31      -0.0339541000
_diffrn_orient_matrix_UB_32      -0.1443073000
_diffrn_orient_matrix_UB_33      0.0132553000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_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            21852
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.524
_diffrn_reflns_theta_min         4.298
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.503
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10822
_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    1.265
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1505 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.041(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3414
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0423P)^2^+0.3928P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0876
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_full    0.943
_reflns_Friedel_fraction_max     0.915
_reflns_number_gt                3395
_reflns_number_total             3414
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc04938j3.cif
_cod_data_source_block           exp_855
_cod_depositor_comments
;Adding full bibliography for 1552766--1552772.cif.

 Adding full bibliography for 1552766--1552772.cif.
;
_cod_database_code               1552768
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.97
_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. Restrained distances
 C182-C192
 1.52 with sigma of 0.01
 C191-C181
 1.52 with sigma of 0.01
 C181-C191
 1.52 with sigma of 0.01
3. Others
 Fixed Sof: C182(0.5) H18A(0.5) H18B(0.5) C192(0.5) H19A(0.5) H19B(0.5)
 H19C(0.5) C191(0.5) H19D(0.5) H19E(0.5) H19F(0.5) C181(0.5) H18C(0.5) H18D(0.5)
4.a Ternary CH refined with riding coordinates:
 C14(H14)
4.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C182(H18A,H18B), C181(H18C,H18D)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11)
4.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C192(H19A,H19B,H19C), C191(H19D,
 H19E,H19F)
;
_shelx_res_checksum              77923
_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 9.557
_oxdiff_exptl_absorpt_empirical_full_min 0.442