Aromatic Nucleophilic Substitution (SNAr) of meso-Nitroporphyrin with Azide and Amines as an Alternative Metal Catalyst Free Synthetic Approach To Obtain meso-N-Substituted Porphyrins.
Devillers, Charles H.; Hebié, Seydou; Lucas, Dominique; Cattey, Hélène; Clément, Sébastien; Richeter, Sébastien; The Journal of organic chemistry 79 (2014) 6424–6434; doi:10.1021/jo5005586

data_4029667
_publ_section_title
;
 Aromatic Nucleophilic Substitution (SNAr) of meso-Nitroporphyrin with
 Azide and Amines as an Alternative Metal Catalyst Free Synthetic Approach
 To Obtain meso-N-Substituted Porphyrins.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6424
_journal_page_last               6434
_journal_paper_doi               10.1021/jo5005586
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         '2(C47 H35 N5 Ni O), C7 H8'
_chemical_formula_sum            'C101 H78 N10 Ni2 O2'
_chemical_formula_weight         1581.15
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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   difmap
_audit_creation_date             2014-01-24
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                75.664(2)
_cell_angle_beta                 72.801(2)
_cell_angle_gamma                86.751(2)
_cell_formula_units_Z            1
_cell_length_a                   10.1608(5)
_cell_length_b                   13.0894(7)
_cell_length_c                   15.4826(8)
_cell_measurement_reflns_used    9324
_cell_measurement_temperature    115
_cell_measurement_theta_max      29.540
_cell_measurement_theta_min      2.506
_cell_volume                     1905.53(17)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius,1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement
'SHELX, G.M. Sheldrick, Acta Cryst.(2008). A64, 112-122'
_computing_structure_solution    'ShelXS-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      115
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean 9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa Apex II'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            47524
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.62
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction. 
wR2(int) was 0.0517 before and 0.0432 after correction. 
The Ratio of minimum to maximum transmission is 0.9064. 
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'dark violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             826
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.716
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         8721
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0543P)^2^+1.3987P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1031
_reflns_number_gt                7598
_reflns_number_total             8721
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5005586_si_002.cif
_cod_data_source_block           1-NH(Ph-(4-MeO))_cd43
_cod_depositor_comments
'Adding full bibliography for 4029666--4029667.cif.'
_cod_database_code               4029667
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C48(0.5) C49(0.5) H49(0.5) C50(0.5) H50(0.5) C51(0.5) H51(0.5)
 C52(0.5) H52(0.5) C53(0.5) H53(0.5) C54(0.5) H54A(0.5) H54B(0.5) H54C(0.5)
3.a Riding coordinates:
 N5(H5)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C9(H9), C13(H13), C14(H14), C18(H18), C19(H19),
 C22(H22), C23(H23), C25(H25), C26(H26), C29(H29), C30(H30), C32(H32), C33(H33),
  C36(H36), C37(H37), C38(H38), C39(H39), C40(H40), C42(H42), C43(H43),
 C45(H45), C46(H46), C49(H49), C50(H50), C51(H51), C52(H52), C53(H53)
3.c Fitted hexagon refined as free rotating group:
 C48(C49,C50,C51,C52,C53)
3.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C34(H34A,H34B,H34C), C47(H47A,H47B,H47C), C54(H54A,H54B,
 H54C)
;