Modular Synthesis of Medium-Sized Fluorinated and Nonfluorinated Heterocyclic Lactones by Sequential CN-Bond-Cleaving Ring Expansion under Pd Catalysis
Uno, Hiroto; Kawai, Koki; Shiro, Motoo; Shibata, Norio; ACS Catalysis  (2020) 14117–14126; doi:10.1021/acscatal.0c03927

data_4518247
_publ_section_title
;
 Modular Synthesis of Medium-Sized Fluorinated and Nonfluorinated
 Heterocyclic Lactones by Sequential CN-Bond-Cleaving Ring Expansion under
 Pd Catalysis
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              14117
_journal_page_last               14126
_journal_paper_doi               10.1021/acscatal.0c03927
_journal_year                    2020
_chemical_formula_moiety         'C26 H25 F2 N O4 S'
_chemical_formula_sum            'C26 H25 F2 N O4 S'
_chemical_formula_weight         485.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.923(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   18.2175(7)
_cell_length_b                   7.7392(3)
_cell_length_c                   16.7579(8)
_cell_measurement_reflns_used    13013
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.29
_cell_volume                     2302.83(18)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18949
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_min         2.294
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1016.00
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.44
_refine_diff_density_min         -0.43
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1248
_refine_ls_R_factor_gt           0.0721
_refine_ls_shift/su_max          0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0421P)^2^+3.1710P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1525
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3411
_reflns_number_total             5230
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            cs0c03927_si_005.cif
_cod_data_source_block           MS064
_cod_original_cell_volume        2302.84(18)
_cod_database_code               4518247
_verf_plat201_alert_2_a
;
PROBLEM: Isotropic non-H Atoms in Main Residues  ....... 15 Report
         F1A F2A O1A O2A C7A C8A etc.

RESPONSE: The atoms in the disordered model were heavily superimposed,
          see _publ_section_exptl_refinement
;
_shelx_res_checksum              3854
_shelx_hkl_checksum              46796