Direct air-induced arylphosphinoyl radicals for the synthesis of benzo[b]phosphole oxides
Huang, Mingqing; Huang, Haiyang; You, Mengyao; Zhang, Xinxin; Sun, Longgen; Chen, Chao; Mei, Zhichao; Yang, Ruchun; Xiao, Qiang; Green Chemistry 26 (2024) 295–299; doi:10.1039/D3GC03947A

data_7247829
_publ_section_title
;
 Direct air-induced arylphosphinoyl radicals for the synthesis of
 benzo[b]phosphole oxides
;
_journal_issue                   1
_journal_name_full               'Green Chemistry'
_journal_page_first              295
_journal_page_last               299
_journal_paper_doi               10.1039/D3GC03947A
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C28 H25 O P, 1[HCCl3]'
_chemical_formula_sum            'C28 H25 O P'
_chemical_formula_weight         408.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-10-10
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2023-10-12 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.577(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.961(2)
_cell_length_b                   9.9168(16)
_cell_length_c                   21.452(3)
_cell_measurement_reflns_used    2409
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.235
_cell_measurement_theta_min      2.280
_cell_volume                     2846.6(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker Smart APEX-II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0952
_diffrn_reflns_av_unetI/netI     0.1130
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16736
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.613
_diffrn_reflns_theta_min         2.556
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0886 before and 0.0341 after correction.
The Ratio of minimum to maximum transmission is 0.9032.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.953
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.836
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         6460
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.836
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0555
_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^)+(0.0666P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1541
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2888
_reflns_number_total             6460
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc03947a3.cif
_cod_data_source_block           221119huanghy2_0m
_cod_depositor_comments
'Adding full bibliography for 7247828--7247829.cif.'
_cod_original_cell_volume        2846.6(8)
_cod_database_code               7247829
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.997
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C3, C4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C13(H13), C12(H12), C15(H15), C3(H3), C5(H5), C2(H2), C22(H22),
 C9(H9), C28(H28), C18(H18), C10(H10), C19(H19), C20(H20), C27(H27), C24(H24),
 C21(H21), C26(H26), C25(H25)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              67502
_shelx_fab_checksum              48363
_olex2_submission_special_instructions 'No special instructions were received'