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_4022185
_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            'C69 H38 Cl2 F16 N4 O2 Zn'
_chemical_formula_weight         1395.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 117.540(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.1116(14)
_cell_length_b                   17.7254(17)
_cell_length_c                   14.2090(15)
_cell_measurement_reflns_used    2623
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      39.607
_cell_measurement_theta_min      4.596
_cell_volume                     3151.4(5)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0755
_diffrn_reflns_av_sigmaI/netI    0.0865
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16733
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83205
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.465
_exptl_crystal_size_mid          0.312
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.016
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         6061
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0832
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1606P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2445
_refine_ls_wR_factor_ref         0.2722
_reflns_number_gt                3566
_reflns_number_total             6061
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061743rsi20060829_101957.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      'P 21/m'
_cod_database_code               4022185