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_7159802
_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         'C0.5 H Cl, C32 H15 F14 N5'
_chemical_formula_sum            'C32.5 H16 Cl F14 N5'
_chemical_formula_weight         777.95
_chemical_name_systematic        5,15-perfluoropropyl-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             2022-01-24
_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                111.2842(18)
_cell_angle_beta                 103.5014(18)
_cell_angle_gamma                95.1944(16)
_cell_formula_units_Z            2
_cell_length_a                   9.21263(19)
_cell_length_b                   12.5354(2)
_cell_length_c                   15.5289(3)
_cell_measurement_reflns_used    18302
_cell_measurement_temperature    295
_cell_measurement_theta_max      72.7210
_cell_measurement_theta_min      3.1660
_cell_volume                     1594.14(6)
_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      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 0.980
_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   -109.00 -53.00   1.00    2.50    --  -40.79 -57.00  46.00   56
  2  \w    -48.00 -14.00   1.00    2.50    --  -40.79 -57.00  46.00   34
  3  \w     88.00 113.00   1.00    2.50    --   40.79  57.00-171.00   25
  4  \w     14.00  41.00   1.00    2.50    --   40.79  57.00-171.00   27
  5  \w     57.00 130.00   1.00   15.00    --  105.59 -57.00  46.00   73
  6  \w     84.00 116.00   1.00   15.00    --  105.59  57.00-171.00   32
  7  \w    -69.00  32.00   1.00    2.50    --  -40.79  57.00-171.00  101
  8  \w    -81.00 -56.00   1.00    2.50    --  -40.79 -77.00-150.00   25
  9  \w    -43.00  -8.00   1.00    2.50    --  -40.79 -77.00-150.00   35
 10  \w   -114.00 -17.00   1.00    2.50    --  -40.79 -38.00 120.00   97
 11  \w     23.00  97.00   1.00    2.50    --   40.79-125.00  30.00   74
 12  \w    -23.00  27.00   1.00    2.50    --   40.79 -57.00  46.00   50
 13  \w      9.00  35.00   1.00    2.50    --   42.00  79.00-166.18   26
 14  \w     11.00  36.00   1.00    2.50    --   46.00  84.00-149.93   25
 15  \w     13.00  39.00   1.00    2.50    --   46.00  79.00-100.68   26
 16  \w     16.00  43.00   1.00    2.50    --   50.00  82.00  47.57   27
 17  \w     17.00  42.00   1.00    2.50    --   50.00  78.00 -51.38   25
 18  \w     16.00  41.00   1.00    2.50    --   50.00  81.00 150.32   25
 19  \w     16.00  41.00   1.00    2.50    --   50.00  82.00 102.64   25
 20  \w     26.00  54.00   1.00    2.50    --   58.00  75.00  -7.48   28
 21  \w     31.00  56.00   1.00    2.50    --   62.00  75.00  96.01   25
 22  \w     30.00  59.00   1.00    2.50    --   62.00  77.00-167.19   29
 23  \w     30.00  56.00   1.00    2.50    --   62.00  77.00  15.55   26
 24  \w     30.00  56.00   1.00    2.50    --   62.00  77.00 -62.03   26
 25  \w     31.00  57.00   1.00    2.50    --   62.00  75.00-123.02   26
 26  \w     36.00  62.00   1.00    2.50    --   66.00  72.00 153.48   26
 27  \w     33.00  63.00   1.00    2.50    --   66.00  77.00-106.59   30
 28  \w     37.00  63.00   1.00    2.50    --   70.00  77.00-164.79   26
 29  \w     39.00  66.00   1.00    2.50    --   70.00  75.00  30.53   27
 30  \w     40.00  69.00   1.00    2.50    --   70.00  77.00  47.72   29
 31  \w     48.00  74.00   1.00   15.00    --   74.00  63.00 132.41   26
 32  \w     42.00  69.00   1.00   15.00    --   74.00  76.00 150.20   27
 33  \w     42.00  74.00   1.00   15.00    --   74.00  75.00 -22.19   32
 34  \w     46.00  77.00   1.00   15.00    --   78.00  74.00 -53.25   31
 35  \w     48.00  78.00   1.00   15.00    --   78.00  73.00 -98.57   30
 36  \w     53.00  87.00   1.00   15.00    --   82.00  62.00  18.51   34
 37  \w     89.00 155.00   1.00   15.00    --   82.00  77.00  81.58   66
 38  \w     52.00  80.00   1.00   15.00    --   82.00  77.00  81.58   28
 39  \w     51.00  80.00   1.00   15.00    --   82.00  70.00-119.00   29
 40  \w    104.00 153.00   1.00   15.00    --   82.00  62.00  18.51   49
 41  \w     55.00  86.00   1.00   15.00    --   86.00  69.00  54.78   31
 42  \w     54.00  80.00   1.00   15.00    --   86.00  75.00 124.93   26
 43  \w    101.00 159.00   1.00   15.00    --   94.00  72.00 167.11   58
 44  \w     63.00  89.00   1.00   15.00    --   94.00  72.00 167.11   26
 45  \w     66.00 101.00   1.00   15.00    --   94.00  69.00-102.53   35
 46  \w    104.00 170.00   1.00   15.00    --   98.00  71.00-117.14   66
 47  \w     65.00  95.00   1.00   15.00    --   98.00  77.00-171.08   30
 48  \w     67.00  98.00   1.00   15.00    --   98.00  71.00-117.14   31
 49  \w     78.00 156.00   1.00   15.00    --  105.59  57.00 -46.68   78
 50  \w     84.00 154.00   1.00   15.00    --  105.59  61.00  90.00   70
 51  \w    147.00 178.00   1.00   15.00    --  105.59 125.00 -60.00   31
 52  \w     73.00  98.00   1.00   15.00    --  105.59  77.00 -60.00   25
 53  \w    110.00 159.00   1.00   15.00    --  105.59  77.00 -90.00   49
 54  \w     95.00 174.00   1.00   15.00    --  105.59 125.00  30.00   79
 55  \w     89.00 118.00   1.00   15.00    --  105.59-125.00  60.00   29
 56  \w     74.00 100.00   1.00   15.00    --  105.59  77.00 -90.00   26
 57  \w     32.00  85.00   1.00   15.00    --  105.59-125.00  60.00   53
 58  \w     73.00 108.00   1.00   15.00    --  105.59  77.00  60.00   35
 59  \w     74.00 117.00   1.00   15.00    --  105.59  77.00   0.00   43
 60  \w     73.00 172.00   1.00   15.00    --  105.59  77.00-150.00   99
 61  \w     76.00 166.00   1.00   15.00    --  105.59  64.00  29.23   90
 62  \w     77.00 171.00   1.00   15.00    --  105.59  77.00 120.00   94
 63  \w     25.00 109.00   1.00   15.00    --  105.59 -94.00  60.00   84
 64  \w     33.00 116.00   1.00   15.00    --  105.59-125.00 -90.00   83
 65  \w     73.00 174.00   1.00   15.00    --  105.59  77.00 -30.00  101
 66  \w     26.00  95.00   1.00   15.00    --  105.59 -94.00 -30.00   69
;
_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      -0.1413905000
_diffrn_orient_matrix_UB_12      0.0255765000
_diffrn_orient_matrix_UB_13      0.0349445000
_diffrn_orient_matrix_UB_21      -0.0851148000
_diffrn_orient_matrix_UB_22      -0.1251428000
_diffrn_orient_matrix_UB_23      -0.0674091000
_diffrn_orient_matrix_UB_31      0.0590742000
_diffrn_orient_matrix_UB_32      -0.0419209000
_diffrn_orient_matrix_UB_33      0.0811663000
_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  0.0225
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28537
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.889
_diffrn_reflns_theta_min         3.188
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.134
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73783
_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    1.621
_exptl_crystal_description       plate
_exptl_crystal_F_000             778
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, Heptane'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.902
_refine_diff_density_min         -0.764
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0035(6)
_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   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         6238
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0728
_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^)+(0.1315P)^2^+1.1831P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2244
_refine_ls_wR_factor_ref         0.2292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5676
_reflns_number_total             6238
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00191e2.cif
_cod_data_source_block           pgj277
_cod_depositor_comments
'Adding full bibliography for 7159800--7159804.cif.'
_cod_original_formula_sum        'C32.50 H16 Cl F14 N5'
_cod_database_code               7159802
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'c32 h15 f14 n5'
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.586
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 Cl1-C33
 1.85 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Cl1 \\sim C33: within 1.9A with sigma of 0.01 and sigma for terminal atoms of
0.001 within 1.9A
4. Others
 Fixed Sof: C33(0.5) H33A(0.5) H33B(0.5) F7(0.75) F8(0.25)
5.a Riding coordinates:
 N1(H1), N2(H2), N4(H4)
5.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4A), C8(H8), C9(H9), C13(H13), C14(H14), C18(H18), C19(H19),
 C24(H24), C25(H25), C27(H27), C28(H28)
;
_shelx_res_checksum              42441
_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 1.512
_oxdiff_exptl_absorpt_empirical_full_min 0.718