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_4035108
_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_sum            'C51 H42 N6 O4'
_chemical_formula_weight         802.90
_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                78.412(2)
_cell_angle_beta                 74.5815(18)
_cell_angle_gamma                73.6581(18)
_cell_formula_units_Z            2
_cell_length_a                   10.9512(5)
_cell_length_b                   11.7033(6)
_cell_length_c                   17.3015(9)
_cell_measurement_reflns_used    9209
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.5444
_cell_measurement_theta_min      3.0101
_cell_volume                     2032.14(18)
_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 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            94686
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         3.011
_diffrn_source                   'sealed tube X-ray source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.2657
_exptl_absorpt_correction_T_min  0.2298
_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            red
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_exptl_crystal_description       plate
_exptl_crystal_F_000             844
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0034(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     600
_refine_ls_number_reflns         10050
_refine_ls_number_restraints     153
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0541
_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^)+(0.0357P)^2^+2.1265P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1324
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7878
_reflns_number_total             10050
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00790_si_002.cif
_cod_data_source_block           ML_034_2_0m
_cod_original_cell_volume        2032.15(18)
_cod_database_code               4035108
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.962
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              88199
_shelx_hkl_checksum              90940