Galactose-conjugates of the oseltamivir pharmacophore—new tools for the characterization of influenza virus neuraminidases
Carbain, Benoit; Martin, Stephen R.; Collins, Patrick J.; Hitchcock, Peter B.; Streicher, Hansjörg; Organic & Biomolecular Chemistry 7 (2009) 2570–2575; doi:10.1039/b903394g

data_7150669
_publ_section_title
;
 Galactose-conjugates of the oseltamivir pharmacophore---new tools for
 the characterization of influenza virus neuraminidases
;
_journal_issue                   12
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              2570
_journal_page_last               2575
_journal_paper_doi               10.1039/b903394g
_journal_volume                  7
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H31 I N2 O4'
_chemical_formula_sum            'C18 H31 I N2 O4'
_chemical_formula_weight         466.35
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2007-12-10T09:33:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 105.910(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.2334(15)
_cell_length_b                   4.9607(6)
_cell_length_c                   18.6244(19)
_cell_measurement_reflns_used    30758
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.022
_cell_measurement_theta_min      3.395
_cell_measurement_wavelength     0.71073
_cell_volume                     1086.9(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.840612E-1
_diffrn_orient_matrix_UB_12      0.165438E-1
_diffrn_orient_matrix_UB_13      -0.85115E-2
_diffrn_orient_matrix_UB_21      0.114724E-1
_diffrn_orient_matrix_UB_22      0.312792E-1
_diffrn_orient_matrix_UB_23      0.546111E-1
_diffrn_orient_matrix_UB_31      0.51994E-2
_diffrn_orient_matrix_UB_32      0.198454
_diffrn_orient_matrix_UB_33      -0.78979E-2
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0922
_diffrn_reflns_av_unetI/netI     0.1148
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7090
_diffrn_reflns_theta_full        25.95
_diffrn_reflns_theta_max         25.95
_diffrn_reflns_theta_min         3.41
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    1.495
_exptl_absorpt_correction_T_max  0.9809
_exptl_absorpt_correction_T_min  0.7795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.275
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.109
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3663
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1334
_refine_ls_R_factor_gt           0.0736
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+3.0678P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1482
_refine_ls_wR_factor_ref         0.1772
_reflns_number_gt                2313
_reflns_number_total             3663
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b903394g.txt
_cod_data_source_block           dec707
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7150669