Syntheses of Pyridine C-Nucleosides as Analogues of the Natural Nucleosides dC and dU
Zhenhua Sun; Shahadat Ahmed; Larry W. McLaughlin; Journal of Organic Chemistry 71 (2006) 2922–2925; doi:10.1021/jo060066y

data_4021620
_publ_contact_author_address
;
Department of Chemistry
Merkert Chemistry Center
Boston College
Chestnut Hill
Massachusetts 02467
;
_publ_contact_author_email       mclaughl@bc.edu
_publ_contact_author_fax         1(617)5520833
_publ_contact_author_name        'Dr Mclaughlin Larry. W.'
_publ_contact_author_phone       1(617)5523622
_publ_section_title
;
 Syntheses of Pyridine C-Nucleosides as Analogues of the Natural
 Nucleosides dC and dU
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2922
_journal_page_last               2925
_journal_paper_doi               10.1021/jo060066y
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration syn
_chemical_formula_iupac          C10H13F1N2O3
_chemical_formula_moiety         'C10 H13 F N2 O3'
_chemical_formula_structural     'C10 H13 F N2 O3'
_chemical_formula_sum            'C10 H13 F N2 O3'
_chemical_formula_weight         228.22
_chemical_melting_point          425
_chemical_name_common
6-Amino-3-(\b-D-2-deoxy-erythrofuranosyl)-2-fluuoropyridine
_chemical_name_systematic
;(2R,3R,5R)-5-(6-amino-2-fluoropyridin-3-yl)-
tetrahydro-2-(hydroxymethyl)furan-3-ol
;
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           'form.cif (version 2.0)'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3295(16)
_cell_length_b                   11.365(3)
_cell_length_c                   13.908(3)
_cell_measurement_reflns_used    3580
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.40
_cell_measurement_theta_min      2.31
_cell_volume                     1000.5(4)
_computing_cell_refinement       'SMART (BRUKER, V5.625, 2001)'
_computing_data_collection       'ASTRO (BRUKER, V5.007, 1997)'
_computing_data_reduction        'SAINT (BRUKER, V6.22, 2001)'
_computing_molecular_graphics    'SHELXTL (BRUKER, 2000, V6.1)'
_computing_publication_material  'XCIF (Sheldrick and BRUKER, 1997, V5.1)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7552
_diffrn_reflns_theta_full        28.40
_diffrn_reflns_theta_max         28.40
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Chunk
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_size_rad          0.2
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(1)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2510
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0513P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0812
_reflns_number_gt                2315
_reflns_number_total             2510
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060066ysi20060113_035032.cif
_cod_database_code               4021620