Total Syntheses of Bulgecins A, B, and C and Their Bactericidal Potentiation of the β-Lactam Antibiotics.
Tomoshige, Shusuke; Dik, David A.; Akabane-Nakata, Masaaki; Madukoma, Chinedu S.; Fisher, Jed F.; Shrout, Joshua D.; Mobashery, Shahriar; ACS infectious diseases 4 (2018) 860–867; doi:10.1021/acsinfecdis.8b00105

data_4516798
_publ_section_title
;
 Total Syntheses of Bulgecins A, B, and C and Their Bactericidal
 Potentiation of the \b-Lactam Antibiotics.
;
_journal_issue                   6
_journal_name_full               'ACS infectious diseases'
_journal_page_first              860
_journal_page_last               867
_journal_paper_doi               10.1021/acsinfecdis.8b00105
_journal_volume                  4
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H35 N O6 Si'
_chemical_formula_sum            'C22 H35 N O6 Si'
_chemical_formula_weight         437.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 123.699(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.6556(10)
_cell_length_b                   6.5523(2)
_cell_length_c                   18.1925(7)
_cell_measurement_reflns_used    9255
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.07
_cell_measurement_theta_min      4.50
_cell_volume                     2345.98(17)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            34934
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.074
_diffrn_reflns_theta_min         2.919
_diffrn_source                   'Incoatec micro-focus'
_exptl_absorpt_coefficient_mu    1.188
_exptl_absorpt_correction_T_max  0.8842
_exptl_absorpt_correction_T_min  0.7298
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.358
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.152
_refine_diff_density_max         1.264
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 2035 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.042(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4600
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0449
_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^)+(0.0947P)^2^+1.6187P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1311
_refine_ls_wR_factor_ref         0.1319
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4547
_reflns_number_total             4600
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            id8b00105_si_002.cif
_cod_data_source_block           nd1709
_cod_original_cell_volume        2345.99(17)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4516798
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.676
_shelx_estimated_absorpt_t_max   0.840
_diffrn_source_monochromator     'MONTEL Multi-layer'
_shelx_res_checksum              51233
_shelx_hkl_checksum              53020