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_4036207
_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_compound_source        'synthesis as described'
_chemical_formula_moiety         'C19 H25 O4 P1'
_chemical_formula_sum            'C19 H25 O4 P'
_chemical_formula_weight         348.36
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2013-10-11T11:32:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6376(2)
_cell_length_b                   9.3332(3)
_cell_length_c                   29.571(1)
_cell_measurement_reflns_used    13705
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.015
_cell_measurement_theta_min      2.288
_cell_measurement_wavelength     0.71073
_cell_volume                     1831.92(10)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            13705
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        26
_diffrn_reflns_theta_max         29.015
_diffrn_reflns_theta_min         2.288
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 589 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.08(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.886
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4492
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.888
_refine_ls_R_factor_all          0.1735
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0564P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1326
_reflns_number_gt                1854
_reflns_number_total             4492
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00548_si_002.cif
_cod_data_source_block           CCDC1048716
_cod_original_formula_sum        'C19 H25 O4 P1'
_cod_database_code               4036207