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_4035908
_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_absolute_configuration unk
_chemical_formula_moiety
'C42 H6 F20 N4 O4, 0.397(C6 H14), 1.206(C H2 Cl2)'
_chemical_formula_sum            'C45.59 H13.97 Cl2.41 F20 N4 O4'
_chemical_formula_weight         1147.15
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   28.859(2)
_cell_length_b                   49.537(3)
_cell_length_c                   12.0811(7)
_cell_measurement_reflns_used    9647
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2587
_cell_measurement_theta_min      3.4005
_cell_volume                     17271.0(19)
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_collection       'Apex3 v2016.9-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_refinement
;  
SHELXL-2016/6 (Sheldrick, 2015, 2016), 
SHELXLE Rev714 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       64
_diffrn_reflns_limit_k_min       -66
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            98628
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         3.268
_diffrn_source                   'sealed tube X-ray source'
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5659
_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    1.765
_exptl_crystal_description       block
_exptl_crystal_F_000             9096
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details
;
?
;
_refine_ls_abs_structure_Flack   0.37(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     834
_refine_ls_number_reflns         9835
_refine_ls_number_restraints     557
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0691
_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^)+(0.0927P)^2^+140.2424P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1810
_refine_ls_wR_factor_ref         0.1974
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                8111
_reflns_number_total             9835
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02628_si_002.cif
_cod_data_source_block           NH_B_77_3_0m
_cod_original_cell_volume        17271(2)
_cod_database_code               4035908
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.922
_shelx_estimated_absorpt_t_max   0.937
_shelx_res_checksum              46890
_shelx_hkl_checksum              73318