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_7159800
_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 H18 F6 N4 O, C6 H6'
_chemical_formula_sum            'C34 H24 F6 N4 O'
_chemical_formula_weight         618.57
_chemical_name_systematic        5,15-bis-trifluoromethyl-10-(p-anisyl)-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             2022-01-20
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-06-02 deposited with the CCDC.	2024-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                102.813(7)
_cell_angle_beta                 106.382(7)
_cell_angle_gamma                97.930(7)
_cell_formula_units_Z            2
_cell_length_a                   10.9445(10)
_cell_length_b                   11.6383(9)
_cell_length_c                   12.2119(9)
_cell_measurement_reflns_used    3697
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3140
_cell_measurement_theta_min      3.9860
_cell_volume                     1421.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.970
_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    -29.00  -1.00   1.00    5.00    --    0.00 105.00 -44.00   28
  2  \w      8.00  36.00   1.00    5.00    --    0.00-105.00-145.00   28
  3  \w    -75.00 -48.00   1.00   10.00    --  -54.96 105.00 -44.00   27
  4  \w   -149.00 -86.00   1.00   10.00    --  -54.96-105.00-145.00   63
  5  \w    102.00 130.00   1.00   10.00    --   54.96 105.00 -44.00   28
  6  \w     28.00 106.00   1.00   10.00    --   54.96-105.00-145.00   78
  7  \w    102.00 129.00   1.00   35.00    --  109.93 105.00 -44.00   27
  8  \w     70.00 112.00   1.00   35.00    --  109.93-105.00-145.00   42
  9  \w    -94.00 -27.00   1.00    5.00    --    0.00 -57.00 150.00   67
 10  \w    -12.00  43.00   1.00    5.00    --    0.00 -57.00 150.00   55
 11  \w   -114.00 -80.00   1.00   10.00    --  -54.96 -99.00 -60.00   34
 12  \w    -91.00  -9.00   1.00   10.00    --  -54.96 125.00  60.00   82
 13  \w   -150.00 -79.00   1.00   10.00    --  -54.96 -99.00 -90.00   71
 14  \w   -134.00 -79.00   1.00   10.00    --  -54.96 -99.00  60.00   55
 15  \w     65.00  92.00   1.00   10.00    --   54.96 -38.00  30.00   27
 16  \w    -36.00 -11.00   1.00   10.00    --   54.96 -38.00  30.00   25
 17  \w     14.00 147.00   1.00   10.00    --   54.96  57.00 -60.00  133
 18  \w    104.00 142.00   1.00   10.00    --   54.96 125.00-180.00   38
 19  \w     95.00 178.00   1.00   35.00    --  109.93  38.00 120.00   83
 20  \w     64.00  91.00   1.00   35.00    --  109.93 -91.00 150.00   27
 21  \w    101.00 170.00   1.00   35.00    --  109.93 111.00 -30.00   69
 22  \w     26.00 150.00   1.00   35.00    --  109.93 -91.00 -60.00  124
 23  \w     63.00  94.00   1.00   35.00    --  109.93  38.00 120.00   31
 24  \w    101.00 152.00   1.00   35.00    --  109.93 -91.00   0.00   51
 25  \w    146.00 177.00   1.00   35.00    --  109.93  63.00  30.00   31
 26  \w     67.00 118.00   1.00   35.00    --  109.93  63.00  30.00   51
 27  \w    135.00 160.00   1.00   35.00    --  109.93  77.00  90.00   25
 28  \w     70.00 139.00   1.00   35.00    --  109.93 178.00-120.00   69
 29  \w    100.00 177.00   1.00   35.00    --  109.93 111.00   0.00   77
 30  \w     73.00 100.00   1.00   35.00    --  109.93  77.00  90.00   27
 31  \w     80.00 112.00   1.00   35.00    --  109.93-111.00  90.00   32
 32  \w     31.00  58.00   1.00   35.00    --  109.93 -91.00 150.00   27
 33  \w     75.00 145.00   1.00   35.00    --  109.93 -50.00-120.00   70
 34  \w    123.00 150.00   1.00   35.00    --  109.93 -91.00 150.00   27
 35  \w    100.00 157.00   1.00   35.00    --  109.93 111.00 -60.00   57
 36  \w     39.00  64.00   1.00   35.00    --  109.93 -91.00   0.00   25
 37  \w     80.00 178.00   1.00   35.00    --  109.93  50.00  60.00   98
;
_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      0.1331637000
_diffrn_orient_matrix_UB_12      -0.0364545000
_diffrn_orient_matrix_UB_13      0.0248907000
_diffrn_orient_matrix_UB_21      0.0422005000
_diffrn_orient_matrix_UB_22      0.0794344000
_diffrn_orient_matrix_UB_23      0.1289114000
_diffrn_orient_matrix_UB_31      -0.0552808000
_diffrn_orient_matrix_UB_32      -0.1080614000
_diffrn_orient_matrix_UB_33      0.0381256000
_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  0.0357
_diffrn_reflns_av_unetI/netI     0.0779
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10539
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.684
_diffrn_reflns_theta_min         3.988
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.993
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       prism
_exptl_crystal_F_000             636
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, Heptane'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     395
_refine_ls_number_reflns         5291
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1320
_refine_ls_R_factor_gt           0.0967
_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^)+(0.1692P)^2^+0.6403P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2826
_refine_ls_wR_factor_ref         0.3258
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3300
_reflns_number_total             5291
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00191e2.cif
_cod_data_source_block           pgj293
_cod_depositor_comments
'Adding full bibliography for 7159800--7159804.cif.'
_cod_database_code               7159800
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'c28 h18 f6 n4 o1'
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.874
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1), N2(H2), N4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4A), C8(H8), C9(H9), C12(H12), C13(H13), C17(H17), C18(H18),
 C21(H21), C22(H22), C24(H24), C25(H25), C29(H29), C30(H30), C31(H31), C32(H32),
  C33(H33), C34(H34)
2.c Fitted hexagon refined as free rotating group:
 C29(C30,C31,C32,C33,C34)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_shelx_res_checksum              51927
_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 1.661
_oxdiff_exptl_absorpt_empirical_full_min 0.683