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_7121559
_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 H31 N5 Ni S, C H Cl3'
_chemical_formula_sum            'C46 H32 Cl3 N5 Ni S'
_chemical_formula_weight         851.88
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-06-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-06-20 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                113.223(2)
_cell_angle_beta                 103.443(2)
_cell_angle_gamma                98.599(2)
_cell_formula_units_Z            2
_cell_length_a                   10.2159(6)
_cell_length_b                   14.3590(8)
_cell_length_c                   15.0898(8)
_cell_measurement_reflns_used    9868
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      3.01
_cell_volume                     1905.05(19)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 CMOS
_diffrn_detector_area_resol_mean '1024 x 1024'
_diffrn_detector_type            'Photon 100'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       '\k-geometry diffractometer triump Mo'
_diffrn_measurement_device_type  'Bruker D8 Venture triumph Mo'
_diffrn_measurement_method       '\f and \w scans''
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            98012
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.702
_diffrn_reflns_theta_min         2.872
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-90C'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.817
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0585 before and 0.0547 after correction. The Ratio of minimum to maximum transmission is 0.9390. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_description       neddle
_exptl_crystal_F_000             876
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.501
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         8844
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0443
_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^)+(0.0492P)^2^+2.9689P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1134
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7197
_reflns_number_total             8844
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc01375f3.cif
_cod_data_source_block           compound_1
_cod_depositor_comments
'Adding full bibliography for 7121559--7121561.cif.'
_cod_database_code               7121559
_publcif_datablock.id            {fcdeecc8-e40c-4f34-8511-59717d17a77a}
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.763
_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. Rigid body (RIGU) restrains
 Cl1, Cl2, Cl3, C46, Cl1A, Cl2A, Cl3A, C46A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(Cl1A)=Sof(Cl2A)=Sof(Cl3A)=Sof(C46A)=Sof(H46A)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=Sof(C46)=Sof(H46)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C46(H46), C46A(H46A)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C9(H9), C13(H13), C14(H14), C18(H18), C19(H19),
 C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C30(H30), C31(H31),
  C34(H34), C35(H35), C36(H36), C37(H37), C38(H38), C40(H40), C41(H41),
 C43(H43), C44(H44)
4.c 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 oil'
_olex2_submission_special_instructions 'No special instructions were received'