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_4036204
_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         'C15 H30 B O2 P'
_chemical_formula_sum            'C15 H30 B O2 P'
_chemical_formula_weight         284.17
_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
;
'Wed Jun 04 17:22:30 2014'
;
_audit_creation_method
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_cell_angle_alpha                90.0
_cell_angle_beta                 96.6403(13)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   6.57388(9)
_cell_length_b                   24.3738(3)
_cell_length_c                   10.48088(15)
_cell_measurement_reflns_used    8699
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.6640
_cell_measurement_theta_min      4.5970
_cell_volume                     1668.09(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_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 0.979
_diffrn_measurement_details
;
  1 omega  -25.00   34.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0146   38.0000  -90.0000 59

  2 omega  -49.00   32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0146   38.0000   30.0000 81

  3 omega  -49.00   36.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0146   38.0000 -150.0000 85

  4 omega   46.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0146 -125.0000  -60.0000 37

  5 omega   36.00   92.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -94.0000    0.0000 56

  6 omega   86.00  129.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -77.0000  -90.0000 43

  7 omega   81.00  173.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719   30.0000  -30.0000 92

  8 omega   58.00   95.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0146 -125.0000  138.0000 37

  9 omega   50.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -94.0000  120.0000 47

 10 omega   55.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -30.0000  120.0000 36

 11 omega   31.00   66.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -30.0000   30.0000 35

 12 omega   32.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -30.0000   60.0000 58

 13 omega   35.00   94.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -94.0000   60.0000 59

 14 omega   35.00  165.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -15.0000  -90.0000 130

 15 omega   51.00  108.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -94.0000 -120.0000 57

 16 omega   36.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -94.0000 -180.0000 54

 17 omega   33.00   79.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -30.0000 -180.0000 46

 18 omega   34.00   95.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -45.0000 -120.0000 61

 19 omega  -69.00   22.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0146   19.0000  150.0000 91
;
_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      -0.0194499000
_diffrn_orient_matrix_UB_12      -0.0629575000
_diffrn_orient_matrix_UB_13      -0.0054225000
_diffrn_orient_matrix_UB_21      -0.0422987000
_diffrn_orient_matrix_UB_22      0.0026460000
_diffrn_orient_matrix_UB_23      -0.1475802000
_diffrn_orient_matrix_UB_31      0.2312855000
_diffrn_orient_matrix_UB_32      -0.0048351000
_diffrn_orient_matrix_UB_33      -0.0098981000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11445
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.770
_diffrn_reflns_theta_min         3.627
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.414
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_description
;
;
_exptl_crystal_F_000             624
_exptl_crystal_size_max          .2
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .07
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 2995 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.013(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         6504
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0346
_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^)+(0.0588P)^2^+0.0776P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0926
_reflns_Friedel_coverage         0.920
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                6393
_reflns_number_total             6504
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00548_si_002.cif
_cod_data_source_block           CCDC1048713
_cod_depositor_comments
;

2020-05-25
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C15 H30 B O2 P)'
_cod_original_formula_sum        'C30 H60 B2 O4 P2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     568.34
_cod_database_code               4036204
_shelxl_version_number           2013-4
_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 B(H,H,H) groups, All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C18(H18), C20(H20), C22(H22)
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), C17(H17A,H17B), C19(H19A,H19B), C21(H21A,H21B),
 C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), B1(H1A,H1B,
 H1C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), B2(H2C,
 H2D,H2E)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3A)
;
_olex2_submission_special_instructions 'No special instructions were received'