A Scalable Synthesis of the Difluoromethyl-allo-threonyl Hydroxamate-Based LpxC Inhibitor LPC-058.
Liang, Xiaofei; Gopalaswamy, Ramesh; Navas, 3rd, Frank; Toone, Eric J.; Zhou, Pei; The Journal of organic chemistry 81 (2016) 4393–4398; doi:10.1021/acs.joc.6b00589

data_4031994
_publ_section_title
;
 A Scalable Synthesis of the Difluoromethyl-allo-threonyl
 Hydroxamate-Based LpxC Inhibitor LPC-058.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4393
_journal_page_last               4398
_journal_paper_doi               10.1021/acs.joc.6b00589
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H27 F2 N O7 S'
_chemical_formula_weight         415.45
_chemical_name_common            XFL-13-32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3347(2)
_cell_length_b                   12.7819(4)
_cell_length_c                   22.8824(7)
_cell_measurement_reflns_used    4987
_cell_measurement_temperature    296
_cell_measurement_theta_max      26.7403
_cell_measurement_theta_min      2.3893
_cell_volume                     1852.78(10)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS Inc., 2009)'
_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS Inc., 2009)'
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            27049
_diffrn_reflns_theta_full        27.40
_diffrn_reflns_theta_max         27.40
_diffrn_reflns_theta_min         1.78
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.278
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0372P)^2^+0.2708P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0708
_reflns_number_gt                3755
_reflns_number_total             4195
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00589_si_002.cif
_cod_data_source_block           I
_cod_database_code               4031994