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_7155329
_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 H43 N3 O Pd'
_chemical_formula_sum            'C40 H43 N3 O Pd'
_chemical_formula_weight         688.17
_chemical_name_systematic
'[2^3^-<i>tert</i>-Butyl-8,12,13,17-tetraethyl-7,18-dimethyl-21-oxyazuliporphyrinato]palladium(ii)'
_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   geom
_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             2016-07-26T15:53:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2016-07-27 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                94.893(4)
_cell_angle_beta                 114.886(3)
_cell_angle_gamma                110.418(3)
_cell_formula_units_Z            2
_cell_length_a                   11.5534(7)
_cell_length_b                   12.8890(8)
_cell_length_c                   13.1228(8)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.1
_cell_measurement_theta_min      2.38
_cell_volume                     1598.20(19)
_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 0.946
_diffrn_measurement_details
;
A total of 3672 frames were collected.  
The total exposure time was 30.60 hours.
;
_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  0.0447
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_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            64514
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.344
_diffrn_reflns_theta_min         1.752
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  0.7436
_exptl_absorpt_correction_T_min  0.7000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex2 v2014.7-1 (Bruker, 2014)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.43
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             716
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.015
_refine_diff_density_max         1.863
_refine_diff_density_min         -1.526
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     618
_refine_ls_number_reflns         10801
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0399P)^2^+1.6280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0957
_reflns_number_gt                8910
_reflns_number_total             10801
_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_original_cell_volume        1598.20(18)
_cod_database_code               7155329
_shelx_estimated_absorpt_t_min   0.886
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              58224