Stereospecific Transformation of Protected P-H Group into P-O or P-N Group in One-Pot Reaction
Qiuli Yao; Chengye Yuan; Journal of Organic Chemistry 77 (2012) 10985–10990; doi:10.1021/jo302140q

data_4027774
_publ_section_title
;
 Stereospecific Transformation of Protected P-H Group into P-O or P-N
 Group in One-Pot Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10985
_journal_page_last               10990
_journal_paper_doi               10.1021/jo302140q
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H30 Br N2 O6 P S'
_chemical_formula_weight         513.38
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.901(3)
_cell_length_b                   13.938(5)
_cell_length_c                   21.180(7)
_cell_measurement_reflns_used    2210
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35.071
_cell_measurement_theta_min      4.831
_cell_volume                     2922.8(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0914
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5409
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    1.560
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44058
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.113
_platon_squeeze_details
;
;
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         5409
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      0.927
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0584
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0728P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1459
_reflns_number_gt                3168
_reflns_number_total             5409
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302140q_si_003.cif
_cod_data_source_block           cd212355
_cod_original_cell_volume        2922.9(16)
_cod_database_code               4027774