C-F Bond Activation by Modified Sulfinatodehalogenation: Facile Synthesis and Properties of Novel Tetrafluorobenzoporphyrins by Direct Intramolecular Cyclization and Reductive Defluorinative Aromatization of Readily Available β-Perfluoroalkylated Porphyrins
Chao Liu; Dong-Mei Shen; Zhuo Zeng; Can-Cheng Guo; Qing-Yun Chen; Journal of Organic Chemistry 71 (2006) 9772–9783; doi:10.1021/jo061743r

data_4022184
_publ_section_title
;
 C-F Bond Activation by Modified Sulfinatodehalogenation:
 Facile Synthesis and Properties of Novel Tetrafluorobenzoporphyrins
 by Direct Intramolecular Cyclization and Reductive Defluorinative
 Aromatization of Readily Available \b-Perfluoroalkylated Porphyrins
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9772
_journal_page_last               9783
_journal_paper_doi               10.1021/jo061743r
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C68 H58 F8 N4 O5 Zn'
_chemical_formula_weight         1228.55
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 94.749(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   33.917(4)
_cell_length_b                   8.8453(11)
_cell_length_c                   20.024(2)
_cell_measurement_reflns_used    4272
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      47.384
_cell_measurement_theta_min      4.566
_cell_volume                     5986.6(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  '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     0.71073
_diffrn_reflns_av_R_equivalents  0.1255
_diffrn_reflns_av_sigmaI/netI    0.1051
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16917
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.490
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77906
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2544
_exptl_crystal_size_max          0.516
_exptl_crystal_size_mid          0.478
_exptl_crystal_size_min          0.345
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6519
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0684
_refine_ls_shift/su_max          0.087
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1103P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1882
_refine_ls_wR_factor_ref         0.2000
_reflns_number_gt                4375
_reflns_number_total             6519
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061743rsi20060829_101932.cif
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4022184