Azobisisobutyronitrile-Initiated Oxidative C-H Functionalization of Simple Alcohols with Diaryl(arylethynyl)phosphine Oxides: A Metal-Free Approach toward Hydroxymethyl Benzo[<i>b</i>]phosphole Oxides and 6<i>H</i>-Indeno[2,1-<i>b</i>]phosphindole 5-Oxide Derivatives.
Guo, Jiami; Mao, Chenlu; Deng, Bin; Ye, Liyi; Yin, Yingwu; Gao, Yuxing; Tu, Song; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00118

data_4038301
_publ_section_title
;
 Azobisisobutyronitrile-Initiated Oxidative C-H Functionalization of
 Simple Alcohols with Diaryl(arylethynyl)phosphine Oxides: A Metal-Free
 Approach toward Hydroxymethyl Benzo[<i>b</i>]phosphole Oxides and
 6<i>H</i>-Indeno[2,1-<i>b</i>]phosphindole 5-Oxide Derivatives.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00118
_journal_year                    2020
_chemical_formula_moiety         'C23 H18 Cl O P'
_chemical_formula_sum            'C23 H18 Cl O P'
_chemical_formula_weight         376.79
_chemical_name_systematic
'8-chloro-6,6-dimethyl-5-phenyl-6H-indeno[2,1-b]phosphindole 5-oxide'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 93.246(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6089(2)
_cell_length_b                   14.0410(3)
_cell_length_c                   17.1323(4)
_cell_measurement_reflns_used    4739
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.28
_cell_measurement_theta_min      4.06
_cell_volume                     1827.42(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10795
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.488
_diffrn_reflns_theta_max         67.488
_diffrn_reflns_theta_min         4.073
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.737
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.53
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            plate
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       colourless
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3277
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0611P)^2^+1.1719P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1158
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2889
_reflns_number_total             3277
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00118_si_002.cif
_cod_data_source_block           C:\X-ray\4865\exp_4865
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038301
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.494
_shelx_estimated_absorpt_t_max   0.947
_shelx_res_checksum              12453
_shelx_hkl_checksum              23359