P-Stereogenic Bicyclo[4.3.1]phosphite Boranes: Synthesis and Utility of Tunable P-Tether Systems for the Desymmetrization of C2-Symmetric 1,3-anti-Diols.
Markley, Jana L.; Hanson, Paul R.; Organic letters 19 (2017) 2552–2555; doi:10.1021/acs.orglett.7b00851

data_1545975
_publ_section_title
;
 P-Stereogenic Bicyclo[4.3.1]phosphite Boranes: Synthesis and Utility of
 Tunable P-Tether Systems for the Desymmetrization of C2-Symmetric
 1,3-anti-Diols.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2552
_journal_page_last               2555
_journal_paper_doi               10.1021/acs.orglett.7b00851
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C8 H14 B O3 P'
_chemical_formula_weight         199.97
_space_group_crystal_system      orthorhombic
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_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
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_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2929(10)
_cell_length_b                   11.2901(17)
_cell_length_c                   14.454(2)
_cell_measurement_reflns_used    7771
_cell_measurement_temperature    100(2)
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_cell_measurement_theta_min      3.06
_cell_volume                     1026.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
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_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
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_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.950
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_diffrn_reflns_theta_max         67.730
_diffrn_reflns_theta_min         4.970
_exptl_absorpt_coefficient_mu    2.166
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.293
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_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
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_refine_diff_density_min         -0.315
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_refine_ls_abs_structure_details
; 
 Flack x determined using 693 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.107(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         1778
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0267
_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^)+(0.0342P)^2^+0.3130P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0701
_reflns_Friedel_coverage         0.645
_reflns_Friedel_fraction_full    0.945
_reflns_Friedel_fraction_max     0.916
_reflns_number_gt                1778
_reflns_number_total             1778
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00851_si_002.cif
_cod_data_source_block           v39c
_cod_depositor_comments
'Adding full bibliography for 1545974--1545975.cif.'
_cod_database_code               1545975
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.535
_shelx_estimated_absorpt_t_max   0.671
_shelx_res_checksum              84043
_shelx_hkl_checksum              91825