Phosphate Tether-Mediated Ring-Closing Metathesis for the Generation of P-Stereogenic, Z-Configured Bicyclo[7.3.1]- and Bicyclo[8.3.1]phosphates.
Markley, Jana L.; Maitra, Soma; Hanson, Paul R.; The Journal of organic chemistry 81 (2016) 899–911; doi:10.1021/acs.joc.5b02473

data_4031906
_publ_section_title
;
 Phosphate Tether-Mediated Ring-Closing Metathesis for the Generation of
 P-Stereogenic, Z-Configured Bicyclo[7.3.1]- and Bicyclo[8.3.1]phosphates.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              899
_journal_page_last               911
_journal_paper_doi               10.1021/acs.joc.5b02473
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H33 O5 P'
_chemical_formula_weight         420.46
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 107.5800(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0855(4)
_cell_length_b                   20.7040(13)
_cell_length_c                   9.2928(6)
_cell_measurement_reflns_used    6628
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.91
_cell_measurement_theta_min      5.43
_cell_volume                     1116.16(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.958
_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  0.0172
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6459
_diffrn_reflns_point_group_measured_fraction_full 0.757
_diffrn_reflns_point_group_measured_fraction_max 0.734
_diffrn_reflns_theta_full        66.000
_diffrn_reflns_theta_max         67.909
_diffrn_reflns_theta_min         5.431
_diffrn_source                   'Bruker MicroStar microfocus rotating anode'
_exptl_absorpt_coefficient_mu    1.342
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       'Rectangular parallelepiped'
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
; 
 Flack x determined using 974 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.109(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         2986
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0255
_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^)+(0.0325P)^2^+0.2450P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0656
_reflns_Friedel_coverage         0.488
_reflns_Friedel_fraction_full    0.518
_reflns_Friedel_fraction_max     0.497
_reflns_number_gt                2983
_reflns_number_total             2986
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02473_si_004.cif
_cod_data_source_block           v71c
_cod_database_code               4031906
_shelx_estimated_absorpt_t_min   0.713
_shelx_estimated_absorpt_t_max   0.866
_shelxl_version_number           2013-4
_shelx_res_checksum              45465
_shelx_hkl_checksum              49349