Two-step access to bis-<i>meso</i>-perfluoroalkyl-corroles towards <i>meso</i>-perfluoroacyl-ABC-corroles.
Julliard, Paul-Gabriel; Pascal, Simon; Siri, Olivier; Giorgi, Michel; Cortés-Arriagada, Diego; Sanhueza, Luis; Canard, Gabriel; Organic & biomolecular chemistry 22 (2024) 1993–1997; doi:10.1039/d4ob00191e

data_7159801
_publ_section_title
;
 Two-step access to bis-<i>meso</i>-perfluoroalkyl-corroles towards
 <i>meso</i>-perfluoroacyl-ABC-corroles.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1993
_journal_page_last               1997
_journal_paper_doi               10.1039/d4ob00191e
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C28 H15 F6 N5'
_chemical_formula_sum            'C28 H15 F6 N5'
_chemical_formula_weight         535.45
_chemical_name_systematic
5,15-bistrifluoromethyl-10-(4-cyanophenyl)-corrole
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-06-02 deposited with the CCDC.	2024-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                80.6513(19)
_cell_angle_beta                 70.8233(19)
_cell_angle_gamma                81.5848(18)
_cell_formula_units_Z            2
_cell_length_a                   8.68015(18)
_cell_length_b                   11.4089(3)
_cell_length_c                   12.5860(3)
_cell_measurement_reflns_used    13541
_cell_measurement_temperature    295
_cell_measurement_theta_max      72.6660
_cell_measurement_theta_min      3.7200
_cell_volume                     1155.81(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_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   -104.00 -77.00   1.00    2.00    --  -40.79-142.00  86.00   27
  2  \w    -32.00  -4.00   1.00    2.00    --  -40.79 128.00 -28.00   28
  3  \w    -94.00 -44.00   1.00    2.00    --  -40.79 142.00 143.00   50
  4  \w     38.00  63.00   1.00    2.00    --   40.79-128.00-102.00   25
  5  \w     39.00 106.00   1.00    2.00    --   40.79-142.00  86.00   67
  6  \w     52.00  77.00   1.00   10.00    --  105.59-128.00-102.00   25
  7  \w     85.00 176.00   1.00   10.00    --  105.59 142.00 143.00   91
  8  \w     57.00  82.00   1.00   10.00    --  105.59-142.00  86.00   25
  9  \w     94.00 157.00   1.00   10.00    --  105.59 128.00 -28.00   63
 10  \w      3.00  28.00   1.00    2.00    --   38.00  84.00 169.26   25
 11  \w     -1.00  24.00   1.00    2.00    --   38.00  94.00  64.09   25
 12  \w    -42.00 -17.00   1.00    2.00    --  -40.79 -38.00-120.00   25
 13  \w   -112.00 -15.00   1.00    2.00    --  -40.79 -57.00 150.00   97
 14  \w   -114.00 -45.00   1.00    2.00    --  -40.79 -38.00-120.00   69
 15  \w      4.00 120.00   1.00    2.00    --   40.79  19.00  30.00  116
 16  \w     11.00  36.00   1.00    2.00    --   46.00  84.00 -42.50   25
 17  \w     16.00  41.00   1.00    2.00    --   50.00  82.00 -24.40   25
 18  \w     16.00  41.00   1.00    2.00    --   50.00  82.00-120.71   25
 19  \w     16.00  41.00   1.00    2.00    --   50.00  82.00  28.61   25
 20  \w     19.00  44.00   1.00    2.00    --   50.00  80.00-164.62   25
 21  \w     18.00  44.00   1.00    2.00    --   50.00  82.00  75.13   26
 22  \w     16.00  42.00   1.00    2.00    --   50.00  82.00 114.80   26
 23  \w     86.00 130.00   1.00    2.00    --   58.00  72.00   9.01   44
 24  \w     29.00  56.00   1.00    2.00    --   58.00  72.00   9.01   27
 25  \w    110.00 135.00   1.00    2.00    --   62.00  75.00-120.89   25
 26  \w     30.00  55.00   1.00    2.00    --   62.00  75.00-120.89   25
 27  \w    117.00 142.00   1.00    2.00    --   66.00  77.00  96.06   25
 28  \w     33.00  59.00   1.00    2.00    --   66.00  77.00 152.45   26
 29  \w    107.00 139.00   1.00    2.00    --   66.00  77.00 -88.03   32
 30  \w     34.00  62.00   1.00    2.00    --   66.00  77.00 -88.03   28
 31  \w     34.00  60.00   1.00    2.00    --   66.00  77.00-175.81   26
 32  \w     34.00  67.00   1.00    2.00    --   66.00  77.00  96.06   33
 33  \w     34.00  60.00   1.00    2.00    --   66.00  76.00 -41.95   26
 34  \w     90.00 116.00   1.00    2.00    --   66.00  77.00 152.45   26
 35  \w     39.00  65.00   1.00    2.00    --   70.00  74.00   1.10   26
 36  \w     39.00 144.00   1.00    2.00    --   70.00  70.00  68.41  105
 37  \w     42.00  67.00   1.00   10.00    --   74.00  77.00-126.27   25
 38  \w     44.00  69.00   1.00   10.00    --   74.00  71.00  33.39   25
 39  \w     45.00  77.00   1.00   10.00    --   78.00  77.00 169.05   32
 40  \w     49.00  78.00   1.00   10.00    --   78.00  74.00  95.48   29
 41  \w     51.00  78.00   1.00   10.00    --   82.00  76.00 -77.04   27
 42  \w     55.00 108.00   1.00   10.00    --   86.00  77.00 102.88   53
 43  \w     62.00 118.00   1.00   10.00    --   90.00  57.00-144.03   56
 44  \w     58.00  83.00   1.00   10.00    --   90.00  77.00 -66.65   25
 45  \w    116.00 142.00   1.00   10.00    --   90.00  77.00 -66.65   26
 46  \w     59.00  84.00   1.00   10.00    --   90.00  74.00  15.19   25
 47  \w    128.00 163.00   1.00   10.00    --   94.00  69.00-126.52   35
 48  \w     65.00  92.00   1.00   10.00    --   94.00  69.00-126.52   27
 49  \w     63.00  89.00   1.00   10.00    --   94.00  70.00 -41.94   26
 50  \w     72.00 172.00   1.00   10.00    --  102.00  64.00  75.82  100
 51  \w     72.00 101.00   1.00   10.00    --  102.00  74.00-127.82   29
 52  \w     73.00 149.00   1.00   10.00    --  105.59  77.00 -30.00   76
 53  \w    110.00 151.00   1.00   10.00    --  105.59  61.00 -60.00   41
 54  \w     81.00 107.00   1.00   10.00    --  105.59  61.00 -60.00   26
 55  \w     73.00 149.00   1.00   10.00    --  105.59  77.00 150.00   76
 56  \w     77.00 103.00   1.00   10.00    --  105.59  66.00 121.27   26
 57  \w     79.00 178.00   1.00   10.00    --  105.59  61.00  30.00   99
 58  \w     76.00 177.00   1.00   10.00    --  105.59  61.00-150.00  101
 59  \w     80.00 178.00   1.00   10.00    --  105.59  61.00 -90.00   98
 60  \w     74.00  99.00   1.00   10.00    --  105.59  77.00  30.00   25
 61  \w     73.00 154.00   1.00   10.00    --  105.59  77.00 120.00   81
 62  \w     42.00 110.00   1.00   10.00    --  105.59 -61.00  30.00   68
 63  \w     35.00 118.00   1.00   10.00    --  105.59-125.00-150.00   83
 64  \w     53.00 108.00   1.00   10.00    --  105.59 -94.00-120.00   55
 65  \w    121.00 159.00   1.00   10.00    --  105.59  77.00  90.00   38
 66  \w     74.00  99.00   1.00   10.00    --  105.59  77.00  90.00   25
 67  \w     86.00 113.00   1.00   10.00    --  105.59-125.00 120.00   27
 68  \w     46.00 129.00   1.00   10.00    --  105.59 -61.00-120.00   83
;
_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      -0.1828774000
_diffrn_orient_matrix_UB_12      0.0397082000
_diffrn_orient_matrix_UB_13      0.0549297000
_diffrn_orient_matrix_UB_21      -0.0173931000
_diffrn_orient_matrix_UB_22      0.0439851000
_diffrn_orient_matrix_UB_23      -0.1182739000
_diffrn_orient_matrix_UB_31      -0.0437923000
_diffrn_orient_matrix_UB_32      -0.1241149000
_diffrn_orient_matrix_UB_33      -0.0066297000
_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  0.0288
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21228
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.632
_diffrn_reflns_theta_min         3.746
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.111a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, Heptane'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0035(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         4510
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0676P)^2^+0.3902P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1314
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4165
_reflns_number_total             4510
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00191e2.cif
_cod_data_source_block           20gc10
_cod_depositor_comments
'Adding full bibliography for 7159800--7159804.cif.'
_cod_original_cell_volume        1155.82(5)
_cod_database_code               7159801
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'c28 h15 f6 n5'
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.793
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Others
 Fixed Sof: F4(0.6) F5(0.6) F6(0.6) F7(0.4) F8(0.4) F9(0.4)
3.a Riding coordinates:
 N1(H1), N2(H2), N4(H4)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4A), C8(H8), C9(H9), C12(H12), C13(H13), C17(H17), C18(H18),
 C23(H23), C24(H24), C26(H26), C27(H27)
;
_shelx_res_checksum              77533
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.316
_oxdiff_exptl_absorpt_empirical_full_min 0.689