Direct meso-Alkynylation of Porphyrins Doubly Assisted by Pyridyl Coordination.
Anabuki, Shoma; Tokuji, Sumito; Aratani, Naoki; Osuka, Atsuhiro; Organic letters 14 (2012) 2778–2781; doi:10.1021/ol301005b

data_1507728
_publ_section_title
;
 Direct meso-Alkynylation of Porphyrins Doubly Assisted by Pyridyl
 Coordination.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2778
_journal_page_last               2781
_journal_paper_doi               10.1021/ol301005b
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C81 H84 N6 Ni O, C6 H6 '
_chemical_formula_sum            'C87 H90 N6 Ni O'
_chemical_formula_weight         1294.36
_chemical_name_systematic
; 
 ? 
;
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.845(5)
_cell_angle_beta                 105.316(5)
_cell_angle_gamma                106.968(5)
_cell_formula_units_Z            2
_cell_length_a                   13.467(5)
_cell_length_b                   16.348(5)
_cell_length_c                   18.590(5)
_cell_measurement_reflns_used    6985
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.95
_cell_measurement_theta_min      2.41
_cell_volume                     3547(2)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_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 8.333
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0460
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17201
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.326
_exptl_absorpt_correction_T_max  0.9682
_exptl_absorpt_correction_T_min  0.8807
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1380
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.824
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1042
_refine_ls_number_reflns         12265
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0591P)^2^+1.5980P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1168
_reflns_number_gt                9768
_reflns_number_total             12265
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301005b_si_004.cif
_cod_data_source_block           20306anabuki_0m
_cod_database_code               1507728