Synthesis and anti-HIV activity of conformationally restricted bicyclic hexahydroisobenzofuran nucleoside analogs
Díaz-Rodríguez, Alba; Sanghvi, Yogesh S.; Fernández, Susana; Schinazi, Raymond F.; Theodorakis, Emmanuel A.; Ferrero, Miguel; Gotor, Vicente; Organic & Biomolecular Chemistry 7 (2009) 1415–1423; doi:10.1039/b818707j

data_7150572
_publ_section_title
;
 Synthesis and anti-HIV activity of conformationally restricted
 bicyclic hexahydroisobenzofuran nucleoside analogs
;
_journal_issue                   7
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              1415
_journal_page_last               1423
_journal_paper_doi               10.1039/b818707j
_journal_volume                  7
_journal_year                    2009
_chemical_formula_sum            'C14 H18 N2 O4'
_chemical_formula_weight         278.30
_chemical_name_common            AD11
_space_group_IT_number           86
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-P 4bc'
_symmetry_space_group_name_H-M   'P 42/n :2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.8916(12)
_cell_length_b                   22.8916(12)
_cell_length_c                   5.224(4)
_cell_measurement_reflns_used    289
_cell_measurement_temperature    208(2)
_cell_measurement_theta_max      23.56
_cell_measurement_theta_min      5.12
_cell_volume                     2738(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      208(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  Siemens
_diffrn_measurement_method       phi
_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  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            7109
_diffrn_reflns_theta_full        20.77
_diffrn_reflns_theta_max         20.77
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9950
_exptl_absorpt_correction_T_min  0.9803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.346
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         1430
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.346
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0675
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0100P)^2^+5.1000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1223
_reflns_number_gt                1317
_reflns_number_total             1430
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b818707j.txt
_cod_data_source_block           theod27
_cod_original_cell_volume        2737.3(19)
_cod_original_sg_symbol_H-M      P4(2)/n
_cod_database_code               7150572