An Alternate Route of Transforming meso-Tetraarylporphyrins to Porpholactams, and Their Conversion to Amine-Functionalized Imidazoloporphyrins.
Luciano, Michael P.; Akhigbe, Joshua; Ding, Jiaming; Thuita, Damaris; Hamchand, Randy; Zeller, Matthias; Brückner, Christian; The Journal of organic chemistry 83 (2018) 9619–9630; doi:10.1021/acs.joc.8b00790

data_4035109
_publ_section_title
;
 An Alternate Route of Transforming meso-Tetraarylporphyrins to
 Porpholactams, and Their Conversion to Amine-Functionalized
 Imidazoloporphyrins.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9619
_journal_page_last               9630
_journal_paper_doi               10.1021/acs.joc.8b00790
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C55 H40 N8, 0.788(C H2 Cl2), 2.212(C H4 O)'
_chemical_formula_sum            'C58 H50.42 Cl1.58 N8 O2.21'
_chemical_formula_weight         950.73
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                97.419(3)
_cell_angle_beta                 102.316(3)
_cell_angle_gamma                109.689(3)
_cell_formula_units_Z            2
_cell_length_a                   9.5189(7)
_cell_length_b                   13.8293(9)
_cell_length_c                   20.6264(14)
_cell_measurement_reflns_used    9814
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      79.3593
_cell_measurement_theta_min      5.0487
_cell_volume                     2437.3(3)
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_collection       'Apex3 v2016.9-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_refinement
;  
SHELXL-2016/6 (Sheldrick, 2015, 2016), 
SHELXLE Rev714 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_unetI/netI     0.0926
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21587
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.820
_diffrn_reflns_theta_min         5.050
_diffrn_source                   'I-mu-S microsource X-ray tube'
_exptl_absorpt_coefficient_mu    1.406
_exptl_absorpt_correction_T_max  0.3295
_exptl_absorpt_correction_T_min  0.1986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       plate
_exptl_crystal_F_000             998
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     655
_refine_ls_number_reflns         9599
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0725
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0708P)^2^+1.7884P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1829
_refine_ls_wR_factor_ref         0.1914
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7518
_reflns_number_total             9599
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00790_si_003.cif
_cod_data_source_block           ML_D42_2_0m
_cod_database_code               4035109
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.639
_shelx_estimated_absorpt_t_max   0.920
_shelx_res_checksum              8867
_shelx_hkl_checksum              8968