Synthesis of Purine Nucleosides Built on a 3-Oxabicyclo[3.2.0]heptane Scaffold
Ramon Flores; Albert Rustullet; Ramon Alibés; Angel Álvarez-Larena; Pedro de March; Marta Figueredo; Josep Font; Journal of Organic Chemistry 76 (2011) 5369–5383; doi:10.1021/jo200775x

data_4026430
_publ_section_title
;
 Synthesis of Purine Nucleosides Built on a 3-Oxabicyclo[3.2.0]heptane
 Scaffold
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5369
_journal_page_last               5383
_journal_paper_doi               10.1021/jo200775x
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C12 H13 F N4 O3'
_chemical_formula_sum            'C12 H13 F N4 O3'
_chemical_formula_weight         280.26
_chemical_name_systematic
;
(1'S,2'S,4'S,5'R)-9-(1'-fluoro-4'-hydroxymethyl-3'-oxabicyclo[3.2.0]
hept-2-yl)-9H-hypoxanthine
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2887(6)
_cell_length_b                   10.5055(6)
_cell_length_c                   11.3704(6)
_cell_measurement_reflns_used    4490
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.58
_cell_measurement_theta_min      2.64
_cell_volume                     1229.00(12)
_computing_cell_refinement       'SAINT 5.0 (Bruker)'
_computing_data_collection       'SMART 5.6 (Bruker)'
_computing_data_reduction        'SAINT 5.0 (Bruker)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL-NT 6.1 (Bruker)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.13
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker SMART-APEX diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8458
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.87
_diffrn_reflns_theta_min         2.64
_diffrn_standards_decay_%        0.0
_diffrn_standards_number         310
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, 2.05'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2972
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0586P)^2^+0.1129P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0907
_reflns_number_gt                2801
_reflns_number_total             2972
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200775x_si_002.cif
_cod_data_source_block           compound53
_cod_database_code               4026430