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_4034904
_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_moiety         'C33 H24 Cl2 N O P, C4 H8 O2'
_chemical_formula_sum            'C37 H32 Cl2 N O3 P'
_chemical_formula_weight         640.50
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.4763(8)
_cell_length_b                   18.3817(10)
_cell_length_c                   25.4001(13)
_cell_measurement_reflns_used    8732
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.474
_cell_measurement_theta_min      2.353
_cell_volume                     6292.0(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      173.01
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1004
_diffrn_reflns_av_unetI/netI     0.0892
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            32407
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_min         2.357
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1205 before and 0.0889 after correction. The Ratio of minimum to maximum transmission is 0.8118. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       block
_exptl_crystal_F_000             2672
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.187
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.0050(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         6813
_refine_ls_number_restraints     82
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.1197
_refine_ls_R_factor_gt           0.0785
_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^)+(0.0836P)^2^+11.3254P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1926
_refine_ls_wR_factor_ref         0.2189
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4454
_reflns_number_total             6813
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00541_si_003.cif
_cod_data_source_block           mo_d8l17017_0m
_cod_database_code               4034904
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.938
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
2. Restrained distances
 O2-C37 = O2-C34 = O3-C34 = O3-C37 = O4-C36 = O4-C35 = O5-C35 = O5-C36
 1.48 with sigma of 0.02
 C37-C36 = C35-C34
 1.53 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C34 \\sim C35 \\sim C36 \\sim C37 \\sim O2 \\sim O5 \\sim O3 \\sim O4: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: H34C(0.5) H34D(0.5) H34A(0.5) H34B(0.5) H35A(0.5) H35B(0.5)
 H35C(0.5) H35D(0.5) H36A(0.5) H36B(0.5) H36C(0.5) H36D(0.5) H37C(0.5)
 H37D(0.5) H37A(0.5) H37B(0.5) O2(0.5) O5(0.5) O3(0.5) O4(0.5)
5.a Ternary CH refined with riding coordinates:
 C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C34(H34C,H34D), C34(H34A,H34B), C35(H35A,H35B), C35(H35C,H35D), C36(H36A,
 H36B), C36(H36C,H36D), C37(H37C,H37D), C37(H37A,H37B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
  C26(H26), C27(H27), C29(H29), C30(H30), C32(H32), C33(H33)
;
_shelx_res_checksum              64414
_shelx_hkl_checksum              53978
_olex2_submission_special_instructions 'No special instructions were received'