Regioselective oxidation and metalation of meso-unsubstituted azuliporphyrins.
Adiraju, Venkata A. K.; Ferrence, Gregory M.; Lash, Timothy D.; Organic & biomolecular chemistry 14 (2016) 10523–10533; doi:10.1039/c6ob02052f

data_7155327
_publ_section_title
;
 Regioselective oxidation and metalation of meso-unsubstituted
 azuliporphyrins.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10523
_journal_page_last               10533
_journal_paper_doi               10.1039/c6ob02052f
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C40 H45 N3 O, 2 C H Cl3'
_chemical_formula_sum            'C42 H47 Cl6 N3 O'
_chemical_formula_weight         822.52
_chemical_name_systematic
'[2^3^-<i>tert</i>-Butyl-8,12,13,17-tetraethyl-7,18-dimethyl-21-oxyazuliporphyrin chloroform solvate'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   iterative
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2016-07-26T18:42:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2016-08-01 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                92.703(3)
_cell_angle_beta                 101.462(3)
_cell_angle_gamma                104.534(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3983(4)
_cell_length_b                   14.6292(6)
_cell_length_c                   16.7263(8)
_cell_measurement_reflns_used    5264
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.25
_cell_measurement_theta_min      2.5
_cell_volume                     1939.34(16)
_computing_cell_refinement       'APEX2 & SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis,2007)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            62093
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.545
_diffrn_reflns_theta_min         1.249
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.482
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex2 v2014.7-1 (Bruker, 2014)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle,
_exptl_crystal_F_000             860
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.892
_refine_diff_density_min         -0.878
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     441
_refine_ls_number_reflns         8929
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0586
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0487P)^2^+2.0974P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1483
_reflns_number_gt                5377
_reflns_number_total             8929
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob02052f3.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7155327--7155329.cif.'
_cod_database_code               7155327
_shelx_estimated_absorpt_t_min   0.936
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              44000
_shelx_fab_checksum              76265