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_4036205
_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 H27 O3 P'
_chemical_formula_sum            'C15 H27 O3 P'
_chemical_formula_weight         286.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date
;
'Fri May 09 15:08:12 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                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   10.51018(11)
_cell_length_b                   11.46665(11)
_cell_length_c                   12.93223(12)
_cell_measurement_reflns_used    5791
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.2070
_cell_measurement_theta_min      5.1420
_cell_volume                     1558.55(3)
_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)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
  1 omega  -55.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0146   77.0000  120.0000 92

  2 omega    5.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0146  -99.0000   60.0000 41

  3 omega   23.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0146 -125.0000   30.0000 72

  4 omega   43.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 40

  5 omega   64.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   90.0000 27

  6 omega   50.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000    0.0000 47

  7 omega   39.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 46

  8 omega   36.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 54

  9 omega  119.00  161.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -150.0000 42

 10 omega  144.00  173.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -90.0000 29

 11 omega   97.00  144.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -120.0000 47

 12 omega   92.00  170.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -30.0000 78

 13 omega   90.00  172.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 82

 14 omega   89.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -90.0000 25

 15 omega   41.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   60.0000 71
;
_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      -0.0667510000
_diffrn_orient_matrix_UB_12      0.1004767000
_diffrn_orient_matrix_UB_13      -0.0575423000
_diffrn_orient_matrix_UB_21      0.0877235000
_diffrn_orient_matrix_UB_22      -0.0193756000
_diffrn_orient_matrix_UB_23      -0.0938410000
_diffrn_orient_matrix_UB_31      -0.0966413000
_diffrn_orient_matrix_UB_32      -0.0870670000
_diffrn_orient_matrix_UB_33      -0.0454869000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7200
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.452
_diffrn_reflns_theta_min         5.155
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87353
_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    1.220
_exptl_crystal_description
;
;
_exptl_crystal_F_000             624
_exptl_crystal_size_max          .24
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .20
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1330 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.009(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3233
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0309
_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^)+(0.0605P)^2^+0.0925P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0864
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                3164
_reflns_number_total             3233
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00548_si_002.cif
_cod_data_source_block           CCDC1048714
_cod_database_code               4036205
_shelxl_version_number           2013-4
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3A), 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), C15(H15A,H15B)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;