Regioselective reaction of 5,15-disubstituted porphyrins with organolithium reagents—synthetic access to 5,10,15-trisubstituted porphyrins and directly meso-meso-linked bisporphyrins
Senge, Mathias O.; Feng, Xiangdong; Journal of the Chemical Society, Perkin Transactions 1  (2000) 3615–; doi:10.1039/b005411i

data_7213412
_publ_section_title
;
 Regioselective reaction of 5,15-disubstituted porphyrins with
 organolithium reagents---synthetic access to 5,10,15-trisubstituted
 porphyrins and directly meso-meso-linked bisporphyrins
;
_journal_issue                   21
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              3615
_journal_paper_doi               10.1039/b005411i
_journal_year                    2000
_chemical_formula_sum            'C36 H28 N4 Ni'
_chemical_formula_weight         575.33
_chemical_name_systematic
; 
 {5-(1-Methylpropyl)-10,20-diphenylporphy-
 rinato}nickel(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.06(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.738(6)
_cell_length_b                   14.973(8)
_cell_length_c                   28.374(15)
_cell_measurement_reflns_used    34
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      40
_cell_measurement_theta_min      20
_cell_volume                     5404(5)
_computing_cell_refinement       'Siemens P3'
_computing_data_collection       'Siemens P3'
_computing_data_reduction        'XDISK, Shelxtl-Plus, Siemens 1994'
_computing_molecular_graphics    'XP, Shelxtl-Plus, Siemens, 1994'
_computing_publication_material  'Shelxtl-Plus, Siemens, 1994'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean n/a
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Siemens P4/RA'
_diffrn_measurement_method       2theta-theta
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0914
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7123
_diffrn_reflns_theta_full        56.37
_diffrn_reflns_theta_max         56.37
_diffrn_reflns_theta_min         3.12
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 198
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    1.289
_exptl_absorpt_correction_T_max  0.9384
_exptl_absorpt_correction_T_min  0.4254
_exptl_absorpt_correction_type   'empirical, XABS2'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2400
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.940
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     570
_refine_ls_number_reflns         7123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1170
_refine_ls_R_factor_gt           0.0786
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1312P)^2^+12.1393P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2048
_refine_ls_wR_factor_ref         0.2365
_reflns_number_gt                4789
_reflns_number_total             7578
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b005411isup1.cif
_cod_data_source_block           ms430
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/d' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1312P)^2^+12.1393P] where P=(Fo^2^+2Fc^2^)/3'
was changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1312P)^2^+12.1393P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7213412