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_4035907
_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         'C53 H18 F20 N6 O6 Os, 0.5(C6 H14), C H Cl3'
_chemical_formula_sum            'C57 H26 Cl3 F20 N6 O6 Os'
_chemical_formula_weight         1567.39
_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
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                63.58(3)
_cell_angle_beta                 87.24(3)
_cell_angle_gamma                88.56(3)
_cell_formula_units_Z            2
_cell_length_a                   13.336(19)
_cell_length_b                   15.94(2)
_cell_length_c                   16.02(2)
_cell_measurement_reflns_used    712
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.90
_cell_measurement_theta_min      2.21
_cell_volume                     3046(7)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Apex2 v2009.7-0 (Bruker, 2009)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_refinement
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev924 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_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  0.1245
_diffrn_reflns_av_unetI/netI     0.2586
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12423
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.529
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.341
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_description       plate
_exptl_crystal_F_000             1530
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.100
_refine_diff_density_max         3.696
_refine_diff_density_min         -2.486
_refine_diff_density_rms         0.218
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     831
_refine_ls_number_reflns         10423
_refine_ls_number_restraints     643
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.2310
_refine_ls_R_factor_gt           0.1458
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2124P)^2^+40.8700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3733
_refine_ls_wR_factor_ref         0.4484
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5260
_reflns_number_total             10423
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02628_si_006.cif
_cod_data_source_block           08mz387_0m_sq
_cod_original_cell_volume        3045(7)
_cod_database_code               4035907
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.512
_shelx_estimated_absorpt_t_max   0.800
_shelx_res_checksum              35990
_shelx_hkl_checksum              15447
_shelx_fab_checksum              30921