One-Pot Synthesis and Conformational Analysis of 6-Membered Cyclic Iodonium Salts.
Caspers, Lucien; Spils, Julian; Damrath, Mattis; Lork, Enno; Nachtsheim, Boris Johannes; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01125

data_4038535
_publ_section_title
;
 One-Pot Synthesis and Conformational Analysis of 6-Membered Cyclic
 Iodonium Salts.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01125
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H14 I, C F3 O3 S'
_chemical_formula_sum            'C20 H14 F3 I O3 S'
_chemical_formula_weight         518.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.6314(4)
_cell_length_b                   19.2653(5)
_cell_length_c                   14.8884(4)
_cell_measurement_reflns_used    9816
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.287
_cell_volume                     3909.89(19)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture CMOS'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            91480
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.414
_diffrn_reflns_theta_min         2.285
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.791
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.5411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1395 before and 0.0510 after correction. The Ratio of minimum to maximum transmission is 0.7243. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_description       block
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.075
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.391(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         19037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0181P)^2^+2.2376P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0497
_refine_ls_wR_factor_ref         0.0530
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                16821
_reflns_number_total             19037
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01125_si_002.cif
_cod_data_source_block           damrathm180702_a
_cod_database_code               4038535
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.775
_shelx_estimated_absorpt_t_min   0.716
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.609(10)
 0.391(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Ternary CH refined with riding coordinates:
 C9(H9), C29(H29)
3.b Aromatic/amide H refined with riding coordinates:
 C0AA(H0AA), C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8),
 C11(H11), C11'(H11'), C12(H12), C12'(H12'), C13(H13), C21(H21), C22(H22),
 C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C31(H31), C31'(H31'),
 C32(H32), C32'(H32'), C33(H33)
;
_olex2_submission_special_instructions 'No special instructions were received'