General and Modular Synthesis of Isomeric 5-Substituted Pyridin-2-yl and 6-Substituted Pyridin-3-yl C-Ribonucleosides Bearing Diverse Alkyl, Aryl, Hetaryl, Amino, Carbamoyl, and Hydroxy Groups
Martin Štefko; Lenka Slavětínská; Blanka Klepetářová; Michal Hocek; Journal of Organic Chemistry 76 (2011) 6619–6635; doi:10.1021/jo200949c

data_4026517
_publ_contact_author_address
;Institute of Organic Chemistry and Biochemistry
Academy of Sciences of the Czech Republic
Flemingovo nam. 2
16010 Prague 6
Czech Republic
;
_publ_contact_author_email       hocek@uochb.cas.cz
_publ_contact_author_fax         '+420 220183559'
_publ_contact_author_name        'Hocek Michal'
_publ_contact_author_phone       '+420 220183324'
_publ_section_title
;
 General and Modular Synthesis of Isomeric 5-Substituted Pyridin-2-yl and
 6-Substituted Pyridin-3-yl C-Ribonucleosides Bearing Diverse Alkyl, Aryl,
 Hetaryl, Amino, Carbamoyl, and Hydroxy Groups
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6619
_journal_page_last               6635
_journal_paper_doi               10.1021/jo200949c
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H15 N1 O4 S1'
_chemical_formula_sum            'C14 H15 N O4 S'
_chemical_formula_weight         293.34
_chemical_name_systematic
1\b-[5-(2-Thienyl)pyridin-2-yl]-1-deoxy-D-ribofuranose
_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
_cell_angle_alpha                90
_cell_angle_beta                 100.351(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.9831(3)
_cell_length_b                   11.6287(8)
_cell_length_c                   11.8750(8)
_cell_measurement_reflns_used    2927
_cell_measurement_temperature    170
_cell_measurement_theta_max      77
_cell_measurement_theta_min      5
_cell_volume                     676.92(8)
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5444
_diffrn_reflns_theta_full        74.170
_diffrn_reflns_theta_max         77.261
_diffrn_reflns_theta_min         5.367
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.254
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       prism
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.35
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.0708
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2417
_refine_ls_number_restraints     41
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.0065680
_refine_ls_shift/su_mean         7.5918036
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 12.0 2.19 8.18 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0808
_refine_ls_wR_factor_gt          0.0678
_refine_ls_wR_factor_ref         0.0678
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2417
_reflns_number_total             2758
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.76
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0554
_oxford_refine_ls_scale          12.75(4)
_oxford_reflns_number_all        2758
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            jo200949c_si_005.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C14 H15 N1 O4 S1'
_cod_database_code               4026517