Catalyst-free aromatic nucleophilic substitution of meso-bromoporphyrins with azide anion: efficient synthesis and structural analyses of meso-azidoporphyrins.
Yamashita, Ken-ichi; Kataoka, Kazuyuki; Asano, Motoko S.; Sugiura, Ken-ichi; Organic letters 14 (2012) 190–193; doi:10.1021/ol202973z

data_1503510
_publ_contact_author             'Ken-ichi Yamashita'
_publ_section_title
;
 Catalyst-free aromatic nucleophilic substitution of meso-bromoporphyrins
 with azide anion: efficient synthesis and structural analyses of
 meso-azidoporphyrins.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              190
_journal_page_last               193
_journal_paper_doi               10.1021/ol202973z
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C32 H18 N10 Ni'
_chemical_formula_weight         601.27
_chemical_name_systematic
; 
[5,15-Diazido-10,20-diphenylporphyrinato]nickel(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.911(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.929(4)
_cell_length_b                   17.419(3)
_cell_length_c                   7.3381(14)
_cell_measurement_reflns_used    4187
_cell_measurement_temperature    223
_cell_measurement_theta_max      22.02
_cell_measurement_theta_min      3.02
_cell_volume                     2541.4(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker XSHELL'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      223
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Bruker SMART CCD area detector system'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            27890
_diffrn_reflns_theta_full        28.04
_diffrn_reflns_theta_max         28.04
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.810
_exptl_absorpt_correction_T_max  0.9683
_exptl_absorpt_correction_T_min  0.7538
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.964
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.825
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.825
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1399P)^2^+1.5692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1488
_refine_ls_wR_factor_ref         0.1854
_reflns_number_gt                3851
_reflns_number_total             5860
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol202973z_si_002.cif
_cod_data_source_block           5b(Ni)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2541.5(9)
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               1503510