Electrophilic Cyclization of Phenylalkynediols to Naphthyl(aryl)iodonium Triflates with Chelating Hydroxyls: Preparation and X-ray Analyses.
Hinkle, Robert J.; Bredenkamp, Sarah E.; Pike, Robert D.; Cheon, Seong Ik; The Journal of organic chemistry 82 (2017) 11781–11786; doi:10.1021/acs.joc.7b01619

data_4032833
_publ_section_title
;
 Electrophilic Cyclization of Phenylalkynediols to Naphthyl(aryl)iodonium
 Triflates with Chelating Hydroxyls: Preparation and X-ray Analyses.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11781
_journal_page_last               11786
_journal_paper_doi               10.1021/acs.joc.7b01619
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C20 H14 F6 I O3, C F3 O3 S'
_chemical_formula_sum            'C21 H14 F9 I O4 S'
_chemical_formula_weight         660.28
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/5
_cell_angle_alpha                90
_cell_angle_beta                 99.566(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6631(15)
_cell_length_b                   6.8524(7)
_cell_length_c                   23.290(2)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.53
_cell_measurement_theta_min      3.06
_cell_volume                     2307.6(4)
_computing_cell_refinement       'SAINTPLUS (Bruker AXS, 2004)'
_computing_data_collection       'APEX2 (Bruker AXS, 2004)'
_computing_data_reduction        SAINTPLUS
_computing_molecular_graphics    'SHELXLE (Hubschle, 2011)'
_computing_publication_material  'Mercury 3.7 (CCDC, 2016)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       '\w and \y'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         Imus
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21460
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         66.989
_diffrn_reflns_theta_min         3.056
_exptl_absorpt_coefficient_mu    12.700
_exptl_absorpt_correction_T_max  0.6605
_exptl_absorpt_correction_T_min  0.0354
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.901
_exptl_crystal_description       needle
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         2.087
_refine_diff_density_min         -2.108
_refine_diff_density_rms         0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         3987
_refine_ls_number_restraints     282
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0958P)^2^+4.7389P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1450
_refine_ls_wR_factor_ref         0.1477
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3693
_reflns_number_total             3987
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01619_si_002.cif
_cod_data_source_block           cu_RJH028_0m_a_salt_2e
_cod_depositor_comments
'Adding full bibliography for 4032829--4032833.cif.'
_cod_database_code               4032833
_shelx_estimated_absorpt_t_min   0.049
_shelx_estimated_absorpt_t_max   0.785
_shelxl_version_number           2014/5
_shelx_res_checksum              90036
_shelx_hkl_checksum              80835