Synthesis, structure and inhibitory activity of a stereoisomer of oseltamivir carboxylate.
Sartori, Andrea; Dell'amico, Luca; Battistini, Lucia; Curti, Claudio; Rivara, Silvia; Pala, Daniele; Kerry, Philip S.; Pelosi, Giorgio; Casiraghi, Giovanni; Rassu, Gloria; Zanardi, Franca; Organic & biomolecular chemistry 12 (2014) 1561–1569; doi:10.1039/c3ob42069h

data_7153590
_publ_section_title
;
 Synthesis, structure and inhibitory activity of a stereoisomer of
 oseltamivir carboxylate.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1561
_journal_page_last               1569
_journal_paper_doi               10.1039/c3ob42069h
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_formula_sum            'C19 H28 N2 O4'
_chemical_formula_weight         348.43
_chemical_melting_point          390.6
_chemical_name_systematic
; 
(S)-5-{(S)-[(S)-2,2-Diethyl-1,3-dioxolan-4-yl][(2-meth
oxyphenyl)amino]methyl}pyrrolidin-2-one
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.34(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.9990(10)
_cell_length_b                   8.0570(10)
_cell_length_c                   14.015(4)
_cell_measurement_temperature    293(2)
_cell_volume                     980.0(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2047
_diffrn_reflns_theta_full        25.61
_diffrn_reflns_theta_max         25.61
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(2)
_refine_ls_extinction_coef       0.039(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         1979
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0630
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1404P)^2^+0.0717P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1802
_refine_ls_wR_factor_ref         0.1875
_reflns_number_gt                1797
_reflns_number_total             1979
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob42069h.txt
_cod_data_source_block           shelxl
_cod_original_cell_volume        980.0(3)
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7153590