Oxidative C-N fusion of pyridinyl-substituted porphyrins.
Berthelot, Mathieu; Hoffmann, Guillaume; Bousfiha, Asmae; Echaubard, Julie; Roger, Julien; Cattey, Hélène; Romieu, Anthony; Lucas, Dominique; Fleurat-Lessard, Paul; Devillers, Charles H.; Chemical communications (Cambridge, England) 54 (2018) 5414–5417; doi:10.1039/c8cc01375f

data_7121560
_publ_section_title
;
 Oxidative C-N fusion of pyridinyl-substituted porphyrins.
;
_journal_issue                   43
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5414
_journal_page_last               5417
_journal_paper_doi               10.1039/c8cc01375f
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C45 H30 N5 Ni S, F6 P'
_chemical_formula_sum            'C45 H30 F6 N5 Ni P S'
_chemical_formula_weight         876.48
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-10-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-12-21 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.226(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.386(3)
_cell_length_b                   20.956(3)
_cell_length_c                   9.2559(16)
_cell_measurement_reflns_used    3141
_cell_measurement_temperature    150
_cell_measurement_theta_max      20.88
_cell_measurement_theta_min      2.54
_cell_volume                     3738.1(10)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150
_diffrn_detector                 CMOS
_diffrn_detector_area_resol_mean '1024 x 1024'
_diffrn_detector_type            'Photon 100'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans''
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'QUAZAR MX multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1438
_diffrn_reflns_av_unetI/netI     0.1349
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            30651
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.055
_diffrn_reflns_theta_max         25.055
_diffrn_reflns_theta_min         3.048
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              'high brilliance microfocus sealed tube, Cu'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0879 before and 0.0705 after correction. The Ratio of minimum to maximum transmission is 0.7864. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             1792
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of pentane and DCM by slow evaporation'
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.793
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     534
_refine_ls_number_reflns         6587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1451
_refine_ls_R_factor_gt           0.0566
_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^)+(0.0464P)^2^+1.2741P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1297
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3492
_reflns_number_total             6587
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc01375f3.cif
_cod_data_source_block           1FusPF6
_cod_depositor_comments
'Adding full bibliography for 7121559--7121561.cif.'
_cod_original_cell_volume        3738.0(11)
_cod_database_code               7121560
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.756
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C25(H25), C40(H40), C22(H22), C18(H18), C41(H41), C44(H44), C23(H23), C4(H4),
 C3(H3), C24(H24), C43(H43), C27(H27), C9(H9), C8(H8), C14(H14), C28(H28),
 C13(H13), C30(H30), C31(H31), C38(H38), C36(H36), C37(H37), C34(H34), C35(H35)
2.b Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C45(H45A,H45B,H45C)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop with oil'
_olex2_submission_special_instructions 'No special instructions were received'