H-adamantylphosphinates as universal precursors of P-stereogenic compounds.
Gatineau, David; Nguyen, Duc Hanh; Hérault, Damien; Vanthuyne, Nicolas; Leclaire, Julien; Giordano, Laurent; Buono, Gérard; The Journal of organic chemistry 80 (2015) 4132–4141; doi:10.1021/acs.joc.5b00548

data_4036203
_publ_section_title
;
 H-adamantylphosphinates as universal precursors of P-stereogenic
 compounds.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4132
_journal_page_last               4141
_journal_paper_doi               10.1021/acs.joc.5b00548
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H34 B O P'
_chemical_formula_sum            'C21 H34 B O P'
_chemical_formula_weight         344.26
_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
_audit_creation_date
;
'Mon Sep 29 19:13:18 2014'
;
_audit_creation_method
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_cell_angle_alpha                90.0
_cell_angle_beta                 100.7363(15)
_cell_angle_gamma                90.0
_cell_formula_units_Z            2
_cell_length_a                   11.28023(18)
_cell_length_b                   6.62379(9)
_cell_length_c                   13.9299(2)
_cell_measurement_reflns_used    6314
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.7980
_cell_measurement_theta_min      3.9800
_cell_volume                     1022.59(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
  1 omega   18.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2867   38.0000    0.0000 26

  2 omega   73.00  100.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698   61.0000  -90.0000 27

  3 omega   74.00  100.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698   61.0000  -60.0000 26

  4 omega   77.00  126.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698   45.0000  -30.0000 49

  5 omega  120.00  167.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698  111.0000    0.0000 47

  6 omega  108.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698   30.0000   90.0000 69

  7 omega   81.00  142.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698  -61.0000   90.0000 61

  8 omega   75.00  105.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698   30.0000   90.0000 30

  9 omega   75.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698   44.0000  167.0000 103

 10 omega   73.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698  -45.0000  -30.0000 25

 11 omega   66.00  107.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698  -94.0000 -150.0000 41

 12 omega   44.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2867 -125.0000 -120.0000 53

 13 omega   24.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2867 -125.0000  -90.0000 47

 14 omega   33.00   59.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698  -94.0000 -150.0000 26

 15 omega   35.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698  -30.0000 -180.0000 56

 16 omega   76.00  145.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698   45.0000  -90.0000 69

 17 omega  136.00  162.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698   77.0000 -120.0000 26

 18 omega  108.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698   77.0000 -150.0000 69

 19 omega   74.00   99.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698   61.0000 -150.0000 25

 20 omega   71.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698   77.0000 -150.0000 27

 21 omega   73.00  101.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698   61.0000 -120.0000 28

 22 omega   75.00  105.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698   45.0000 -120.0000 30

 23 omega   71.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698   77.0000  -90.0000 26

 24 omega   77.00  140.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698   45.0000  -60.0000 63

 25 omega   73.00   99.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698   77.0000  -60.0000 26

 26 omega   71.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698   77.0000 -120.0000 26

 27 omega   37.00   66.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698  -45.0000  -30.0000 29

 28 omega   35.00   60.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698  -61.0000   90.0000 25

 29 omega    4.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2867   44.0000  167.0000 92

 30 omega  -32.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.2867  -57.0000  150.0000 25

 31 omega  -47.00    7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.2867   38.0000   90.0000 54

 32 omega  -63.00  -37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.2867  -77.0000  -90.0000 26

 33 omega  -34.00    1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.2867  -77.0000  -90.0000 35

 34 omega  -93.00   -1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.2867  -38.0000  -90.0000 92

 35 omega -115.00  -78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.2867 -125.0000  120.0000 37

 36 omega -122.00  -85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.2867  -99.0000   60.0000 37

 37 omega  -98.00  -73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.2867  -57.0000  150.0000 25

 38 omega -129.00 -103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.2867  -77.0000  -90.0000 26

 39 omega -116.00  -76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.2867  -57.0000  -90.0000 40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1082777000
_diffrn_orient_matrix_UB_12      -0.0038096000
_diffrn_orient_matrix_UB_13      -0.0856713000
_diffrn_orient_matrix_UB_21      0.0720664000
_diffrn_orient_matrix_UB_22      0.1268167000
_diffrn_orient_matrix_UB_23      -0.0619776000
_diffrn_orient_matrix_UB_31      0.0489922000
_diffrn_orient_matrix_UB_32      -0.1949038000
_diffrn_orient_matrix_UB_33      -0.0386675000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7804
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.895
_diffrn_reflns_theta_min         3.989
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.200
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_description
;
;
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1676 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3908
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0295
_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^)+(0.0525P)^2^+0.0662P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0795
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.928
_reflns_number_gt                3839
_reflns_number_total             3908
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00548_si_002.cif
_cod_data_source_block           CCDC1048712
_cod_database_code               4036203
_shelxl_version_number           2014/6
_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 C(H,H) groups
 At 1.5 times of:
  All B(H,H,H) groups, All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,
 H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), B1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'