Organocatalytic, Chemoselective Hydrophosphenylation/oxa-Michael Addition Cascade toward Diastereo- and Enantioenriched 1,3-Dihydroisobenzofuryl Phosphonates.
Hazra, Gurupada; Pratap, Shiv; Ghorai, Prasanta; The Journal of organic chemistry 83 (2018) 9654–9666; doi:10.1021/acs.joc.8b01048

data_4035021
_publ_section_title
;
 Organocatalytic, Chemoselective Hydrophosphenylation/oxa-Michael Addition
 Cascade toward Diastereo- and Enantioenriched 1,3-Dihydroisobenzofuryl
 Phosphonates.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9654
_journal_page_last               9666
_journal_paper_doi               10.1021/acs.joc.8b01048
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_sum            'C18 H19 Br N O5 P'
_chemical_formula_weight         440.22
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 96.411(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1638(4)
_cell_length_b                   7.3976(4)
_cell_length_c                   18.5628(10)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      24.62
_cell_measurement_theta_min      2.86
_cell_volume                     977.58(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            33559
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.932
_diffrn_reflns_theta_min         2.861
_exptl_absorpt_coefficient_mu    2.212
_exptl_absorpt_correction_T_max  0.7042
_exptl_absorpt_correction_T_min  0.4572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/4'
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       Rod
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1209 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.052(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4661
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0443P)^2^+0.6909P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1195
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                3393
_reflns_number_total             4661
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01048_si_002.cif
_cod_data_source_block           7b
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4035021
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.472
_shelx_estimated_absorpt_t_max   0.809
_shelx_res_checksum              14960
_shelx_hkl_checksum              42435