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_4035909
_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         '2(C54 H20 F20 N6 O4 Os), C6 H14, 5(C H Cl3)'
_chemical_formula_sum            'C119 H59 Cl15 F40 N12 O8 Os2'
_chemical_formula_weight         3456.93
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                115.910(4)
_cell_angle_beta                 90.019(5)
_cell_angle_gamma                92.124(5)
_cell_formula_units_Z            1
_cell_length_a                   13.330(4)
_cell_length_b                   16.128(5)
_cell_length_c                   16.174(5)
_cell_measurement_reflns_used    8564
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.5865
_cell_measurement_theta_min      2.5335
_cell_volume                     3125.0(17)
_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-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev882 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0909
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_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       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            30865
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         1.400
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.475
_exptl_absorpt_correction_T_max  0.512
_exptl_absorpt_correction_T_min  0.154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.
(2015). J. Appl. Cryst. 48 3-10.
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.837
_exptl_crystal_description       block
_exptl_crystal_F_000             1688
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.290
_refine_diff_density_max         6.777
_refine_diff_density_min         -3.784
_refine_diff_density_rms         0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1077
_refine_ls_number_reflns         15345
_refine_ls_number_restraints     671
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1234
_refine_ls_R_factor_gt           0.0992
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1626P)^2^+30.2913P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2531
_refine_ls_wR_factor_ref         0.2812
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12306
_reflns_number_total             15345
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02628_si_005.cif
_cod_data_source_block           05mz176_0m_new
_cod_original_cell_volume        3124.8(16)
_cod_database_code               4035909
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.371
_shelx_estimated_absorpt_t_max   0.534
_shelx_res_checksum              11008
_shelx_hkl_checksum              80099