One-Pot Benzo[b]phosphole Synthesis through Sequential Alkyne Arylmagnesiation, Electrophilic Trapping, and Intramolecular Phospha-Friedel-Crafts Cyclization.
Wu, Bin; Chopra, Rena; Yoshikai, Naohiko; Organic letters 17 (2015) 5666–5669; doi:10.1021/acs.orglett.5b02950

data_1540605
_publ_section_title
;
 One-Pot Benzo[b]phosphole Synthesis through Sequential Alkyne
 Arylmagnesiation, Electrophilic Trapping, and Intramolecular
 Phospha-Friedel-Crafts Cyclization.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5666
_journal_page_last               5669
_journal_paper_doi               10.1021/acs.orglett.5b02950
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C38 H25 O P'
_chemical_formula_weight         528.55
_chemical_name_systematic
'10,11,12-Triphenyl-10H-phenanthro[9,10-f]phosphindole 10-oxide'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                67.996(5)
_cell_angle_beta                 82.773(6)
_cell_angle_gamma                76.624(6)
_cell_formula_units_Z            2
_cell_length_a                   10.332(2)
_cell_length_b                   10.435(2)
_cell_length_c                   13.632(3)
_cell_measurement_reflns_used    1199
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      21.8134
_cell_measurement_theta_min      2.6430
_cell_volume                     1324.5(5)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Bruker AXS Inc., 2014)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1327
_diffrn_reflns_av_unetI/netI     0.1179
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24352
_diffrn_reflns_theta_full        25.69
_diffrn_reflns_theta_max         25.69
_diffrn_reflns_theta_min         2.03
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.433
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.1224
_refine_ls_R_factor_gt           0.0585
_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^)+(0.0550P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1468
_reflns_number_gt                2971
_reflns_number_total             5018
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02950_si_002.cif
_cod_data_source_block           I
_cod_database_code               1540605
_shelx_res_checksum              74614
_shelx_hkl_checksum              24573