Stereoselective Synthesis, Docking, and Biological Evaluation of Difluoroindanediol-Based MenE Inhibitors as Antibiotics.
Evans, Christopher E.; Matarlo, Joe S.; Tonge, Peter J.; Tan, Derek S.; Organic letters 18 (2016) 6384–6387; doi:10.1021/acs.orglett.6b03272

data_1555967
_publ_section_title
;
 Stereoselective Synthesis, Docking, and Biological Evaluation of
 Difluoroindanediol-Based MenE Inhibitors as Antibiotics.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6384
_journal_page_last               6387
_journal_paper_doi               10.1021/acs.orglett.6b03272
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration R,R,R
_chemical_formula_moiety         'C12 H7 F2 O4, C8 H11 N2 O2, C H4 O'
_chemical_formula_sum            'C21 H22 F2 N2 O7'
_chemical_formula_weight         452.40
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.828(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.014(4)
_cell_length_b                   9.450(3)
_cell_length_c                   18.211(5)
_cell_measurement_reflns_used    9426
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      70.89
_cell_measurement_theta_min      2.45
_cell_volume                     2213.1(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Diamond 4.2.0'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker Apex-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14285
_diffrn_reflns_point_group_measured_fraction_full 0.864
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.881
_diffrn_reflns_theta_min         2.455
_diffrn_source                   ImuS
_exptl_absorpt_coefficient_mu    0.971
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.6912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS;Sheldrick1996;Blessing,ActaC.1995,A51,33
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       columnar
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1377 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.338
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         3562
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.338
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0305
_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^)+(0.0400P)^2^+0.6141P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0816
_reflns_Friedel_coverage         0.644
_reflns_Friedel_fraction_full    0.732
_reflns_Friedel_fraction_max     0.699
_reflns_number_gt                3536
_reflns_number_total             3562
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03272_si_001.cif
_cod_data_source_block           C_0m
_cod_original_cell_volume        2213.0(11)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               1555967
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              43310
_shelx_hkl_checksum              49195