Lewis Acid-Controlled Regioselective Phosphorylation of 2-Indolylmethanols with Diarylphosphine Oxides: Synthesis of Highly Substituted Indoles.
Hu, Chen; Hong, Gang; He, Yuchen; Zhou, Chen; Kozlowski, Marisa C.; Wang, Limin; The Journal of organic chemistry 83 (2018) 4739–4753; doi:10.1021/acs.joc.8b00541

data_4034903
_publ_section_title
;
 Lewis Acid-Controlled Regioselective Phosphorylation of
 2-Indolylmethanols with Diarylphosphine Oxides: Synthesis of Highly
 Substituted Indoles.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4739
_journal_page_last               4753
_journal_paper_doi               10.1021/acs.joc.8b00541
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C34 H28 Cl4 N O2 P'
_chemical_formula_weight         655.34
_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   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 110.0340(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0969(3)
_cell_length_b                   24.9962(7)
_cell_length_c                   13.2961(4)
_cell_measurement_reflns_used    8650
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      54.991
_cell_measurement_theta_min      4.574
_cell_volume                     3152.67(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            55408
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         1.822
_exptl_absorpt_coefficient_mu    0.459
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.834
_refine_diff_density_min         -0.843
_refine_diff_density_rms         0.056
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         5850
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.259
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0643
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0925P)^2^+3.2950P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1730
_refine_ls_wR_factor_ref         0.1898
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4692
_reflns_number_total             5850
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00541_si_002.cif
_cod_data_source_block           mo_d8v17423_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4034903
_shelx_estimated_absorpt_t_min   0.922
_shelx_estimated_absorpt_t_max   0.947
_shelxl_version_number           2013-4
_shelx_res_checksum              910
_shelx_hkl_checksum              1958