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_7159803
_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, 0.5(C6 H6)'
_chemical_formula_sum            'C31 H21 F6 N4'
_chemical_formula_weight         1127.03
_chemical_name_systematic        5,15-bis-trifluoromethyl-10-(p-tolyl)-corrole
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-02
_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                90
_cell_angle_beta                 93.2727(13)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.5597(4)
_cell_length_b                   11.55887(18)
_cell_length_c                   19.1588(3)
_cell_measurement_reflns_used    19843
_cell_measurement_temperature    295
_cell_measurement_theta_max      70.3090
_cell_measurement_theta_min      3.8190
_cell_volume                     5208.88(15)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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     46.00  96.00   1.00    5.00    --    0.00 -18.00  64.00   50
  2  \w    -76.00  24.00   1.00    5.00    --    0.00 -18.00  64.00  100
  3  \w    -27.00 156.00   1.00   20.00    --   54.96 -18.00  64.00  183
  4  \w     94.00 121.00   1.00   30.00    --  109.93 -18.00  64.00   27
  5  \w     58.00 102.00   1.00    5.00    --    0.00 178.00   0.00   44
  6  \w    -62.00 -11.00   1.00   20.00    --  -54.96 -77.00  30.00   51
  7  \w    -78.00 -52.00   1.00   20.00    --  -54.96 -57.00 -60.00   26
  8  \w    -80.00 -41.00   1.00   20.00    --  -54.96 125.00 -30.00   39
  9  \w    -99.00 -12.00   1.00   20.00    --  -54.96 -77.00 -30.00   87
 10  \w    -56.00 -30.00   1.00   20.00    --  -54.96 -57.00 -30.00   26
 11  \w    -29.00  -4.00   1.00   20.00    --  -54.96 125.00 -30.00   25
 12  \w     15.00  91.00   1.00   20.00    --   54.96  77.00   0.00   76
 13  \w    110.00 148.00   1.00   20.00    --   54.96  57.00 120.00   38
 14  \w    110.00 142.00   1.00   20.00    --   54.96 125.00  60.00   32
 15  \w    105.00 142.00   1.00   20.00    --   54.96 125.00-150.00   37
 16  \w    132.00 157.00   1.00   20.00    --   54.96  77.00   0.00   25
 17  \w     33.00  58.00   1.00   20.00    --   54.96  77.00 -60.00   25
 18  \w     97.00 124.00   1.00   20.00    --   54.96 125.00 120.00   27
 19  \w     65.00  91.00   1.00   30.00    --  109.93  77.00 -11.77   26
 20  \w    134.00 161.00   1.00   30.00    --  109.93 111.00  90.00   27
 21  \w     67.00  93.00   1.00   30.00    --  109.93  63.00  30.00   26
 22  \w     65.00  91.00   1.00   30.00    --  109.93  77.00 -60.00   26
 23  \w     66.00  92.00   1.00   30.00    --  109.93  69.00  31.60   26
 24  \w     66.00 178.00   1.00   30.00    --  109.93  67.00 -85.30  112
 25  \w     65.00  91.00   1.00   30.00    --  109.93  77.00 -30.00   26
 26  \w     85.00 149.00   1.00   30.00    --  109.93 178.00  90.00   64
 27  \w     65.00  93.00   1.00   30.00    --  109.93  77.00   0.00   28
 28  \w     65.00 176.00   1.00   30.00    --  109.93  77.00-111.18  111
 29  \w     66.00  92.00   1.00   30.00    --  109.93  73.00 -60.12   26
 30  \w     65.00  91.00   1.00   30.00    --  109.93  77.00  30.00   26
 31  \w     68.00  95.00   1.00   30.00    --  109.93  77.00  32.98   27
 32  \w     67.00 162.00   1.00   30.00    --  109.93  63.00   0.00   95
 33  \w     67.00 177.00   1.00   30.00    --  109.93  58.00 -43.60  110
 34  \w     69.00  96.00   1.00   30.00    --  109.93  63.00 -90.00   27
 35  \w     67.00  92.00   1.00   30.00    --  109.93  68.00 -73.36   25
 36  \w     67.00  93.00   1.00   30.00    --  109.93  63.00 -30.00   26
 37  \w     75.00 100.00   1.00   30.00    --  109.93  66.00 -88.73   25
 38  \w     69.00 176.00   1.00   30.00    --  109.93  50.00  30.00  107
 39  \w     67.00 173.00   1.00   30.00    --  109.93  63.00 -60.00  106
 40  \w     66.00  97.00   1.00   30.00    --  109.93  77.00-120.00   31
 41  \w     67.00 115.00   1.00   30.00    --  109.93  50.00   0.00   48
 42  \w     67.00  92.00   1.00   30.00    --  109.93  68.00 -80.38   25
 43  \w    110.00 170.00   1.00   30.00    --  109.93  50.00  60.00   60
 44  \w     18.00 158.00   1.00   30.00    --  109.93 -38.00-150.00  140
 45  \w     19.00 111.00   1.00   30.00    --  109.93-111.00  60.00   92
 46  \w     69.00  94.00   1.00   30.00    --  109.93  18.00-127.00   25
;
_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      0.0114060000
_diffrn_orient_matrix_UB_12      -0.0274175000
_diffrn_orient_matrix_UB_13      -0.0766232000
_diffrn_orient_matrix_UB_21      0.0639032000
_diffrn_orient_matrix_UB_22      0.0225011000
_diffrn_orient_matrix_UB_23      0.0157637000
_diffrn_orient_matrix_UB_31      0.0087612000
_diffrn_orient_matrix_UB_32      -0.1284800000
_diffrn_orient_matrix_UB_33      0.0191229000
_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  0.0323
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            48813
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.594
_diffrn_reflns_theta_min         3.758
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.995
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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    1.437
_exptl_crystal_description       prism
_exptl_crystal_F_000             2312
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, Heptane'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     729
_refine_ls_number_reflns         9928
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0765
_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^)+(0.1397P)^2^+2.5925P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2300
_refine_ls_wR_factor_ref         0.2463
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8305
_reflns_number_total             9928
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00191e2.cif
_cod_data_source_block           pgj301
_cod_depositor_comments
;
Adding full bibliography for 7159800--7159804.cif.

2024-11-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C62 H42 F12 N8'
_cod_original_formula_weight         1127.03
_cod_original_formula_moiety         '2(C28 H18 F6 N4), C6 H6'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        5208.88(14)
_cod_database_code               7159803
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'c40 h18 f30 n4'
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.811
_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. Rigid body (RIGU) restrains
 C57, C58, C59, C60, C61, C62
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Riding coordinates:
 N1(H1), N2(H2), N4(H4), N5(H5), N6(H6), N8(H8A)
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),
 C21(H21), C22(H22), C24(H24), C25(H25), C31(H31), C32(H32), C36(H36), C37(H37),
  C40(H40), C41(H41), C45(H45), C46(H46), C49(H49), C50(H50), C52(H52),
 C53(H53), C62(H62), C57(H57), C58(H58), C59(H59), C60(H60), C61(H61)
3.c Fitted hexagon refined as free rotating group:
 C62(C57,C58,C59,C60,C61)
3.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C54(H54A,H54B,H54C)
;
_shelx_res_checksum              67998
_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 1.303
_oxdiff_exptl_absorpt_empirical_full_min 0.844