#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:53:44 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180321 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/35/7153590.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7153590
loop_
_publ_author_name
'Sartori, Andrea'
'Dell'amico, Luca'
'Battistini, Lucia'
'Curti, Claudio'
'Rivara, Silvia'
'Pala, Daniele'
'Kerry, Philip S.'
'Pelosi, Giorgio'
'Casiraghi, Giovanni'
'Rassu, Gloria'
'Zanardi, Franca'
_publ_section_title
;
 Synthesis, structure and inhibitory activity of a stereoisomer of
 oseltamivir carboxylate.
;
_journal_issue                   10
_journal_name_full               'Organic & 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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.1404P)²+0.0717P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O2 O 0.3692(4) -0.0766(4) 0.1844(3) 0.0901(11) Uani 1 1 d .
N2 N 0.6632(3) 0.1883(4) 0.3441(2) 0.0588(7) Uani 1 1 d .
O4 O 0.7899(3) 0.3859(5) 0.4904(2) 0.0826(9) Uani 1 1 d .
N1 N 0.5920(4) -0.1590(4) 0.4205(2) 0.0633(8) Uani 1 1 d .
O1 O 0.4477(4) -0.3627(4) 0.4681(3) 0.0847(9) Uani 1 1 d .
C5 C 0.6055(4) 0.0416(4) 0.2861(3) 0.0549(7) Uani 1 1 d .
C13 C 0.8673(4) 0.3771(5) 0.4198(3) 0.0601(8) Uani 1 1 d .
C6 C 0.4293(4) 0.0557(6) 0.2500(3) 0.0639(8) Uani 1 1 d .
O3 O 0.2409(5) 0.1547(6) 0.1150(3) 0.1082(14) Uani 1 1 d .
C12 C 0.9993(4) 0.4671(6) 0.4182(4) 0.0743(11) Uani 1 1 d .
H25 H 1.0422 0.5393 0.4699 0.089 Uiso 1 1 calc R
C8 C 0.7984(3) 0.2683(4) 0.3409(2) 0.0535(7) Uani 1 1 d .
C4 C 0.6656(4) -0.1209(5) 0.3427(3) 0.0570(8) Uani 1 1 d .
C1 C 0.5143(4) -0.3047(5) 0.4106(3) 0.0613(8) Uani 1 1 d .
C9 C 0.8693(4) 0.2545(6) 0.2640(3) 0.0696(10) Uani 1 1 d .
H22 H 0.8274 0.1847 0.2108 0.083 Uiso 1 1 calc R
C2 C 0.5230(5) -0.3834(5) 0.3141(3) 0.0677(9) Uani 1 1 d .
H2 H 0.4235 -0.3790 0.2657 0.081 Uiso 1 1 calc R
H1 H 0.5552 -0.4984 0.3243 0.081 Uiso 1 1 calc R
C7 C 0.3722(6) 0.2092(6) 0.1895(4) 0.0828(13) Uani 1 1 d .
C10 C 1.0025(5) 0.3445(9) 0.2659(3) 0.0867(14) Uani 1 1 d .
H23 H 1.0492 0.3322 0.2146 0.104 Uiso 1 1 calc R
C3 C 0.6414(5) -0.2819(5) 0.2797(3) 0.0679(10) Uani 1 1 d .
H3 H 0.6039 -0.2557 0.2099 0.081 Uiso 1 1 calc R
H4 H 0.7374 -0.3427 0.2902 0.081 Uiso 1 1 calc R
C11 C 1.0660(5) 0.4510(7) 0.3426(4) 0.0869(14) Uani 1 1 d .
H24 H 1.1539 0.5116 0.3425 0.104 Uiso 1 1 calc R
C14 C 0.8509(6) 0.4821(11) 0.5755(4) 0.112(2) Uani 1 1 d .
H28 H 0.7832 0.4767 0.6181 0.168 Uiso 1 1 calc R
H26 H 0.8606 0.5953 0.5566 0.168 Uiso 1 1 calc R
H27 H 0.9505 0.4400 0.6099 0.168 Uiso 1 1 calc R
C15 C 0.2386(7) -0.0216(8) 0.1095(4) 0.0931(15) Uani 1 1 d DU
C16 C 0.2474(10) -0.0794(14) 0.0111(6) 0.140(3) Uani 1 1 d U
H16A H 0.1517 -0.0502 -0.0367 0.168 Uiso 1 1 calc R
H16B H 0.2542 -0.1996 0.0127 0.168 Uiso 1 1 calc R
C17 C 0.3789(16) -0.0128(18) -0.0253(8) 0.186(5) Uani 1 1 d U
H17A H 0.3742 -0.0590 -0.0892 0.278 Uiso 1 1 calc R
H17B H 0.4749 -0.0430 0.0203 0.278 Uiso 1 1 calc R
H17C H 0.3715 0.1059 -0.0302 0.278 Uiso 1 1 calc R
C18 C 0.0894(8) -0.089(2) 0.1333(6) 0.167(5) Uani 1 1 d DU
H18A H 0.1006 -0.2083 0.1383 0.201 Uiso 1 1 calc R
H18B H 0.0922 -0.0489 0.1991 0.201 Uiso 1 1 calc R
C19 C -0.0558(16) -0.059(4) 0.0764(11) 0.314(14) Uani 1 1 d DU
H19A H -0.1290 -0.1059 0.1078 0.471 Uiso 1 1 calc R
H19B H -0.0687 -0.1098 0.0126 0.471 Uiso 1 1 calc R
H19C H -0.0723 0.0581 0.0685 0.471 Uiso 1 1 calc R
H9 H 0.381(5) 0.066(6) 0.302(3) 0.060(10) Uiso 1 1 d .
H8 H 0.635(4) 0.045(6) 0.230(3) 0.049(8) Uiso 1 1 d .
H7 H 0.643(4) 0.188(6) 0.405(3) 0.049(9) Uiso 1 1 d .
H11 H 0.452(7) 0.258(10) 0.164(4) 0.11(2) Uiso 1 1 d .
H10 H 0.330(8) 0.289(12) 0.242(5) 0.12(2) Uiso 1 1 d .
H5 H 0.761(6) -0.085(8) 0.376(3) 0.077(13) Uiso 1 1 d .
H6 H 0.608(6) -0.100(9) 0.465(4) 0.091(18) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 O2 C15 110.1(4)
C8 N2 C5 123.2(3)
C13 O4 C14 119.2(4)
C1 N1 C4 115.6(3)
N2 C5 C6 108.0(3)
N2 C5 C4 112.1(3)
C6 C5 C4 114.9(3)
O4 C13 C12 126.1(4)
O4 C13 C8 113.5(3)
C12 C13 C8 120.4(4)
O2 C6 C7 103.7(3)
O2 C6 C5 110.0(3)
C7 C6 C5 114.4(3)
C7 O3 C15 110.2(4)
C11 C12 C13 121.2(4)
N2 C8 C9 124.9(3)
N2 C8 C13 117.9(3)
C9 C8 C13 117.1(3)
N1 C4 C3 103.2(3)
N1 C4 C5 113.3(3)
C3 C4 C5 115.9(3)
O1 C1 N1 126.5(4)
O1 C1 C2 125.5(4)
N1 C1 C2 107.9(3)
C10 C9 C8 120.7(4)
C1 C2 C3 105.3(3)
O3 C7 C6 104.6(4)
C11 C10 C9 121.1(4)
C2 C3 C4 105.9(3)
C12 C11 C10 119.5(4)
O3 C15 O2 105.8(4)
O3 C15 C16 111.2(7)
O2 C15 C16 110.6(6)
O3 C15 C18 109.5(8)
O2 C15 C18 108.9(6)
C16 C15 C18 110.6(7)
C15 C16 C17 116.4(8)
C19 C18 C15 124.2(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C6 1.418(5)
O2 C15 1.423(6)
N2 C8 1.388(4)
N2 C5 1.450(5)
O4 C13 1.354(5)
O4 C14 1.407(6)
N1 C1 1.354(5)
N1 C4 1.451(5)
O1 C1 1.219(5)
C5 C6 1.536(5)
C5 C4 1.552(5)
C13 C12 1.397(5)
C13 C8 1.419(5)
C6 C7 1.510(6)
O3 C7 1.423(6)
O3 C15 1.423(7)
C12 C11 1.355(7)
C8 C9 1.396(5)
C4 C3 1.552(5)
C1 C2 1.514(6)
C9 C10 1.394(6)
C2 C3 1.520(6)
C10 C11 1.376(8)
C15 C16 1.477(9)
C15 C18 1.563(11)
C16 C17 1.506(15)
C18 C19 1.359(14)
