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_1503509
_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 H19 N7 Ni'
_chemical_formula_weight         560.25
_chemical_name_systematic
; 
[5-Azido-10,20-diphenylporphyrinato]nickel(II) 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
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_cell_length_b                   6.2950(6)
_cell_length_c                   34.930(3)
_cell_measurement_reflns_used    3644
_cell_measurement_temperature    93
_cell_measurement_theta_max      25.60
_cell_measurement_theta_min      2.33
_cell_volume                     4850.6(7)
_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      93
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_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
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_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            25893
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.839
_exptl_absorpt_correction_T_max  0.9514
_exptl_absorpt_correction_T_min  0.6286
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
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_refine_diff_density_max         0.843
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_refine_ls_R_factor_all          0.0854
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_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^)+(0.0760P)^2^+1.0849P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
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_reflns_number_gt                3888
_reflns_number_total             5387
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol202973z_si_002.cif
_cod_data_source_block           2b(Ni)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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        4850.7(8)
_cod_original_sg_symbol_H-M      'Pbca '
_cod_database_code               1503509