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_4038300
_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         'C22 H19 O2 P'
_chemical_formula_sum            'C22 H19 O2 P'
_chemical_formula_weight         346.34
_chemical_name_systematic
'2-(1-hydroxyethyl)-1,3-diphenylphosphindole 1-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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                99.412(4)
_cell_angle_beta                 113.277(4)
_cell_angle_gamma                107.356(4)
_cell_formula_units_Z            2
_cell_length_a                   9.5029(4)
_cell_length_b                   10.3608(5)
_cell_length_c                   11.0975(4)
_cell_measurement_reflns_used    4331
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.9430
_cell_measurement_theta_min      4.5680
_cell_volume                     907.31(9)
_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 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.930
_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  0.0491
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9366
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.734
_diffrn_reflns_theta_min         4.580
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.428
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52865
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3410
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0491
_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^)+(0.0823P)^2^+0.4855P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1509
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3014
_reflns_number_total             3410
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00118_si_001.cif
_cod_data_source_block           exp_2209
_cod_original_cell_volume        907.31(7)
_cod_database_code               4038300
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.763
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C22(H22), C21(H21), C20(H20), C18(H18), C10(H10),
 C14(H14), C6(H6), C19(H19), C12(H12), C13(H13), C11(H11)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              44115
_shelx_hkl_checksum              54159
_olex2_submission_special_instructions 'No special instructions were received'