Regioselective Synthesis of Benzo[b]phosphole Derivatives via Direct ortho-Alkenylation and Cyclization of Arylthiophosphinamides.
Unoh, Yuto; Yokoyama, Yuki; Satoh, Tetsuya; Hirano, Koji; Miura, Masahiro; Organic letters 18 (2016) 5436–5439; doi:10.1021/acs.orglett.6b02868

data_1555892
_publ_section_title
;
 Regioselective Synthesis of Benzo[b]phosphole Derivatives via Direct
 ortho-Alkenylation and Cyclization of Arylthiophosphinamides.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5436
_journal_page_last               5439
_journal_paper_doi               10.1021/acs.orglett.6b02868
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C31 H31 F3 N O3 P S2'
_chemical_formula_sum            'C31 H31 F3 N O3 P S2'
_chemical_formula_weight         617.68
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   19.87(3)
_cell_length_b                   16.30(2)
_cell_length_c                   8.985(12)
_cell_measurement_reflns_used    3912
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.10
_cell_volume                     2910(7)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15'
_computing_molecular_graphics    'CrystalStructure 4.2.1'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 13.653
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1566
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            26451
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         3.057
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1288.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.58
_refine_diff_density_min         -0.38
_refine_ls_abs_structure_details
;
 Flack x determined using 866 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.36(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     370
_refine_ls_number_reflns         6657
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1886
_refine_ls_R_factor_gt           0.1115
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1094P)^2^+0.9019P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2346
_refine_ls_wR_factor_ref         0.2773
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3610
_reflns_number_total             6657
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol6b02868_si_003.cif
_cod_data_source_block           2981-19
_cod_database_code               1555892
_shelx_res_checksum              86150
_shelx_hkl_checksum              88386