One-pot synthesis of functionalized bis(trifluoromethylated)benziodoxoles from iodine(I) precursors.
Milzarek, Tobias M.; Ramirez, Nieves P.; Liu, Xing-Yu; Waser, Jerome; Chemical communications (Cambridge, England) 59 (2023) 12637–12640; doi:10.1039/d3cc04525k

data_7132299
_publ_section_title
;
 One-pot synthesis of functionalized bis(trifluoromethylated)benziodoxoles
 from iodine(I) precursors.
;
_journal_issue                   84
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12637
_journal_page_last               12640
_journal_paper_doi               10.1039/d3cc04525k
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C21 H24 Cl F6 I O2'
_chemical_formula_sum            'C21 H24 Cl F6 I O2'
_chemical_formula_weight         584.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-22
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-09-12 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.8561(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.94012(13)
_cell_length_b                   12.9377(2)
_cell_length_c                   9.96505(14)
_cell_measurement_reflns_used    10897
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.7220
_cell_measurement_theta_min      3.4150
_cell_volume                     1149.99(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.95a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.95a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -118.00  -8.00   1.00    2.00    --  -40.66 -23.00-100.00  110
  2  \w    -43.00 -18.00   1.00    2.00    --  -40.66  23.00  65.00   25
  3  \w     48.00 107.00   1.00    2.00    --   40.66  23.00  65.00   59
  4  \w     98.00 135.00   1.00    8.00    --  112.00  23.00  65.00   37
  5  \w    153.00 178.00   1.00    8.00    --  112.00  23.00  65.00   25
  6  \w     59.00  98.00   1.00    8.00    --  112.00 -23.00-100.00   39
  7  \w    -77.00 -50.00   1.00    2.00    --  -40.66 -57.00-180.00   27
  8  \w   -112.00 -16.00   1.00    2.00    --  -40.66 -38.00-180.00   96
  9  \w     30.00  89.00   1.00    2.00    --   40.66-125.00 150.00   59
 10  \w     28.00  95.00   1.00    2.00    --   40.66-125.00 -30.00   67
 11  \w     32.00  59.00   1.00    2.00    --   40.66  38.00-150.00   27
 12  \w      8.00  35.00   1.00    2.00    --   40.66 -99.00-120.00   27
 13  \w     -5.00  20.00   1.00    2.00    --   40.66 -23.00-100.00   25
 14  \w     14.00  87.00   1.00    2.00    --   40.66  57.00-180.00   73
 15  \w     20.00  47.00   1.00    2.00    --   40.66  57.00-120.00   27
 16  \w     83.00 109.00   1.00    8.00    --  112.00  61.00 120.00   26
 17  \w    126.00 172.00   1.00    8.00    --  112.00  77.00  60.00   46
 18  \w     86.00 178.00   1.00    8.00    --  112.00  45.00 150.00   92
 19  \w     86.00 152.00   1.00    8.00    --  112.00  48.00 126.52   66
 20  \w     29.00  66.00   1.00    8.00    --  112.00 -94.00 120.00   37
 21  \w    144.00 170.00   1.00    8.00    --  112.00  55.00 170.74   26
 22  \w     31.00  81.00   1.00    8.00    --  112.00 -94.00 -60.00   50
 23  \w     84.00 113.00   1.00    8.00    --  112.00  55.00 170.74   29
 24  \w     30.00  98.00   1.00    8.00    --  112.00 -94.00 -30.00   68
 25  \w    137.00 164.00   1.00    8.00    --  112.00  61.00  90.00   27
 26  \w    114.00 177.00   1.00    8.00    --  112.00  61.00-150.00   63
 27  \w     87.00 141.00   1.00    8.00    --  112.00  45.00-150.00   54
 28  \w     59.00  96.00   1.00    8.00    --  112.00 -61.00  90.00   37
 29  \w     87.00 112.00   1.00    8.00    --  112.00  45.00-120.00   25
 30  \w     84.00 109.00   1.00    8.00    --  112.00  61.00 150.00   25
 31  \w     84.00 111.00   1.00    8.00    --  112.00  61.00  90.00   27
 32  \w     87.00 114.00   1.00    8.00    --  112.00  45.00 120.00   27
 33  \w     86.00 113.00   1.00    8.00    --  112.00  53.00-151.57   27
 34  \w     77.00 128.00   1.00    8.00    --  112.00 -45.00 -60.00   51
 35  \w     84.00 109.00   1.00    8.00    --  112.00  61.00-120.00   25
 36  \w     83.00 110.00   1.00    8.00    --  112.00  62.00 153.81   27
 37  \w     84.00 109.00   1.00    8.00    --  112.00  61.00-180.00   25
 38  \w     94.00 121.00   1.00    8.00    --  112.00  45.00  90.00   27
 39  \w     75.00 107.00   1.00    8.00    --  112.00 -94.00 120.00   32
 40  \w     39.00  83.00   1.00    8.00    --  112.00-111.00-150.00   44
 41  \w     92.00 117.00   1.00    8.00    --  112.00  30.00-150.00   25
 42  \w     88.00 115.00   1.00    8.00    --  112.00  30.00 120.00   27
 43  \w     42.00 136.00   1.00    8.00    --  112.00 -61.00 -30.00   94
 44  \w     83.00 110.00   1.00    8.00    --  112.00  61.00-150.00   27
 45  \w     48.00  94.00   1.00    8.00    --  112.00 -94.00-150.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0298805000
_diffrn_orient_matrix_UB_12      0.0336156000
_diffrn_orient_matrix_UB_13      -0.1476557000
_diffrn_orient_matrix_UB_21      0.1682787000
_diffrn_orient_matrix_UB_22      -0.0107551000
_diffrn_orient_matrix_UB_23      -0.0216529000
_diffrn_orient_matrix_UB_31      -0.0247192000
_diffrn_orient_matrix_UB_32      -0.1137572000
_diffrn_orient_matrix_UB_33      -0.0416047000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12606
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.067
_diffrn_reflns_theta_min         4.447
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    12.598
_exptl_absorpt_correction_T_max  0.485
_exptl_absorpt_correction_T_min  0.147
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.95a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_description       prism
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.148
_refine_diff_density_max         0.810
_refine_diff_density_min         -0.745
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.008(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4506
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0306
_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^)+(0.0637P)^2^+0.3882P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0793
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    0.890
_reflns_Friedel_fraction_max     0.872
_reflns_number_gt                4498
_reflns_number_total             4506
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04525k2.cif
_cod_data_source_block           tm-03-67
_cod_database_code               7132299
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C21 H24 O2 F6 Cl1 I1'
_shelx_estimated_absorpt_t_max   0.257
_shelx_estimated_absorpt_t_min   0.166
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,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:
 C13(H13), C16(H16), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C10(H10)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              88702
_shelx_hkl_checksum              10699
_olex2_date_sample_data_collection 2023-07-20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.986
_oxdiff_exptl_absorpt_empirical_full_min 0.462