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_4035906
_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         'C64 H30 F20 N8 O8 Os2, C5 H12, 2(C H Cl3)'
_chemical_formula_sum            'C71 H44 Cl6 F20 N8 O8 Os2'
_chemical_formula_weight         2110.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.412(4)
_cell_length_b                   21.631(4)
_cell_length_c                   30.193(5)
_cell_measurement_reflns_used    8530
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.58
_cell_measurement_theta_min      2.16
_cell_volume                     14637(4)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1527
_diffrn_reflns_av_unetI/netI     0.1046
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            111415
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.349
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.802
_exptl_absorpt_correction_T_max  0.833
_exptl_absorpt_correction_T_min  0.244
_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            green
_exptl_crystal_density_diffrn    1.915
_exptl_crystal_description       plate
_exptl_crystal_F_000             8192
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.050
_refine_diff_density_max         3.820
_refine_diff_density_min         -2.307
_refine_diff_density_rms         0.195
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1038
_refine_ls_number_reflns         12925
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1639
_refine_ls_R_factor_gt           0.0971
_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^)+(0.0816P)^2^+252.9537P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2096
_refine_ls_wR_factor_ref         0.2435
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7179
_reflns_number_total             12925
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02628_si_004.cif
_cod_data_source_block           06mz050_0m_new
_cod_database_code               4035906
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.176
_shelx_estimated_absorpt_t_max   0.833
_shelx_res_checksum              12695
_shelx_hkl_checksum              225