Bacterio- and Isobacteriodilactones by Stepwise or Direct Oxidations of meso-Tetrakis(pentafluorophenyl)porphyrin.
Hewage, Nisansala; Daddario, Pedro; Lau, Kimberly S. F.; Guberman-Pfeffer, Matthew J; Gascón, José A; Zeller, Matthias; Lee, Christal O.; Khalil, Gamal E.; Gouterman, Martin; Brückner, Christian; The Journal of organic chemistry 84 (2019) 239–256; doi:10.1021/acs.joc.8b02628

data_4035904
_publ_section_title
;
 Bacterio- and Isobacteriodilactones by Stepwise or Direct Oxidations of
 meso-Tetrakis(pentafluorophenyl)porphyrin.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              239
_journal_page_last               256
_journal_paper_doi               10.1021/acs.joc.8b02628
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety
'C66 H34 F20 N8 O9 Os2 Zn, 3(C H Cl3), 0.37(H2 O)'
_chemical_formula_sum            'C69 H37.75 Cl9 F20 N8 O9.38 Os2 Zn'
_chemical_formula_weight         2273.64
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90.035(4)
_cell_angle_beta                 95.751(4)
_cell_angle_gamma                104.451(4)
_cell_formula_units_Z            2
_cell_length_a                   10.010(3)
_cell_length_b                   17.046(3)
_cell_length_c                   23.122(4)
_cell_measurement_reflns_used    6627
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.586
_cell_measurement_theta_min      2.676
_cell_volume                     3799.9(15)
_computing_cell_refinement       'SAINT+ 6.45 (Bruker, 2003)'
_computing_data_collection       'SMART 5.630 (Bruker, 1997-2002)'
_computing_data_reduction        'SAINT+ 6.45'
_computing_structure_refinement
;  
SHELXL-2014/7 (Sheldrick, 2014), 
SHELXLE Rev740 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0739
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            37268
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         1.500
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    4.077
_exptl_absorpt_correction_T_max  0.500
_exptl_absorpt_correction_T_min  0.272
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS in SAINT+ (Bruker, 2003)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.987
_exptl_crystal_description       plate
_exptl_crystal_F_000             2195.4
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.170
_refine_diff_density_max         5.021
_refine_diff_density_min         -2.626
_refine_diff_density_rms         0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1121
_refine_ls_number_reflns         37268
_refine_ls_number_restraints     118
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0659
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0734P)^2^+24.8166P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1603
_refine_ls_wR_factor_ref         0.1691
_reflns_Friedel_coverage         0.000
_reflns_number_gt                28000
_reflns_number_total             37268
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02628_si_007.cif
_cod_data_source_block           06mz024m
_cod_original_cell_volume        3799.9(14)
_cod_database_code               4035904
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.338
_shelx_estimated_absorpt_t_max   0.544
_shelx_res_checksum              60872
_shelx_hkl_checksum              65350