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_7159804
_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         'C40 H18 F30 N4 O'
_chemical_formula_sum            'C40 H18 F30 N4 O'
_chemical_formula_weight         1140.58
_chemical_name_systematic        5,15-perfluoroheptyl-10-(p-anisyl)-corrole
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-04
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-06-02 deposited with the CCDC.	2024-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.141(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.1959(7)
_cell_length_b                   9.9152(4)
_cell_length_c                   23.9000(9)
_cell_measurement_reflns_used    5752
_cell_measurement_temperature    295
_cell_measurement_theta_max      73.1340
_cell_measurement_theta_min      3.7630
_cell_volume                     4230.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.51a (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 1.000
_diffrn_measured_fraction_theta_max 0.987
_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      6.00  62.00   1.00   10.00    --    0.00  67.00 -44.00   56
  2  \w    -72.00  17.00   1.00   10.00    --    0.00 -67.00-178.00   89
  3  \w     33.00 146.00   1.00   15.00    --   59.22  67.00 -44.00  113
  4  \w     11.00  82.00   1.00   15.00    --   59.22 -67.00-178.00   71
  5  \w     89.00 173.00   1.00   45.00    --  118.43  67.00 -44.00   84
  6  \w     38.00 139.00   1.00   45.00    --  118.43 -67.00-178.00  101
  7  \w      4.00  48.00   1.00   10.00    --    0.00 -99.00  30.00   44
  8  \w    -98.00 -72.00   1.00   15.00    --  -59.22 -45.00  60.00   26
  9  \w    -89.00 -64.00   1.00   15.00    --  -59.22 125.00-180.00   25
 10  \w    -49.00 -24.00   1.00   15.00    --  -59.22 125.00-180.00   25
 11  \w   -146.00-119.00   1.00   15.00    --  -59.22 -45.00  60.00   27
 12  \w   -145.00-113.00   1.00   15.00    --  -59.22 -94.00 -60.00   32
 13  \w     23.00 117.00   1.00   15.00    --   59.22-125.00  30.00   94
 14  \w     20.00 147.00   1.00   15.00    --   59.22  45.00  60.00  127
 15  \w     95.00 145.00   1.00   15.00    --   59.22 125.00 -90.00   50
 16  \w     95.00 124.00   1.00   15.00    --   59.22 125.00-120.00   29
 17  \w     46.00  73.00   1.00   15.00    --   59.22  45.00  90.00   27
 18  \w     71.00  98.00   1.00   45.00    --  118.43-111.00 -30.00   27
 19  \w    122.00 148.00   1.00   45.00    --  118.43 111.00   0.00   26
 20  \w     83.00 162.00   1.00   45.00    --  118.43  50.00  90.00   79
 21  \w     76.00 166.00   1.00   45.00    --  118.43  38.00 -90.00   90
 22  \w     77.00 103.00   1.00   45.00    --  118.43  63.00  60.00   26
 23  \w     77.00 172.00   1.00   45.00    --  118.43  77.00  30.00   95
 24  \w    153.00 178.00   1.00   45.00    --  118.43 111.00  90.00   25
 25  \w     77.00 162.00   1.00   45.00    --  118.43  63.00   0.00   85
 26  \w    139.00 175.00   1.00   45.00    --  118.43 111.00 -60.00   36
 27  \w     43.00 112.00   1.00   45.00    --  118.43-111.00 120.00   69
 28  \w    134.00 170.00   1.00   45.00    --  118.43  63.00  60.00   36
 29  \w    103.00 177.00   1.00   45.00    --  118.43 111.00 -90.00   74
 30  \w     80.00 106.00   1.00   45.00    --  118.43  63.00  30.00   26
 31  \w     84.00 110.00   1.00   45.00    --  118.43  50.00  30.00   26
 32  \w     30.00 100.00   1.00   45.00    --  118.43-111.00  60.00   70
;
_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      -0.0818614000
_diffrn_orient_matrix_UB_12      -0.0422305000
_diffrn_orient_matrix_UB_13      -0.0224916000
_diffrn_orient_matrix_UB_21      0.0268659000
_diffrn_orient_matrix_UB_22      -0.1109975000
_diffrn_orient_matrix_UB_23      -0.0364263000
_diffrn_orient_matrix_UB_31      0.0047317000
_diffrn_orient_matrix_UB_32      -0.1002469000
_diffrn_orient_matrix_UB_33      0.0498250000
_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  0.0362
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            31602
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.771
_diffrn_reflns_theta_min         2.475
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.848
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.51a (Rigaku Oxford Diffraction, 2022)
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    1.791
_exptl_crystal_description       plate
_exptl_crystal_F_000             2256
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, Heptane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     752
_refine_ls_number_reflns         8688
_refine_ls_number_restraints     211
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.1331
_refine_ls_R_factor_gt           0.0921
_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^)+(0.1000P)^2^+5.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2365
_refine_ls_wR_factor_ref         0.2692
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4972
_reflns_number_total             8688
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00191e2.cif
_cod_data_source_block           pgj306
_cod_depositor_comments
'Adding full bibliography for 7159800--7159804.cif.'
_cod_database_code               7159804
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.709
_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. Restrained distances
 C31-C32
 1.5 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
C32 \\sim F16: within 1.8A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 1.8A
Uanis(F28) = Uanis(F29)
4. Rigid body (RIGU) restrains
 C29, C31, C32, C33, F5, F6, F11, F12, F14, F15, F17, F18, F19, F7, F13, F16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C38, C39, C40, F30, F31, F33, F34, F36, F38, F39, F32, F35, F37
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: F5(0.75) F9(0.75) F12(0.75) F15(0.75) F19(0.75) F28(0.75)
 F31(0.75) F34(0.75) F39(0.75) H3(0.5) H4(0.5) F7(0.25) F10(0.25) F13(0.25)
 F16(0.25) F20(0.25) F29(0.25) F32(0.25) F35(0.25) F37(0.25)
6.a Riding coordinates:
 N1(H1), N2(H2)
6.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N4(H4), C3(H3A), C4(H4A), C8(H8), C9(H9), C12(H12), C13(H13),
 C17(H17), C18(H18), C21(H21), C22(H22), C24(H24), C25(H25)
6.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_shelx_res_checksum              941
_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 1.671
_oxdiff_exptl_absorpt_empirical_full_min 0.758