Synthesis of 2,6-disubstituted pyridin-3-yl C-2'-deoxyribonucleosides through chemoselective transformations of bromo-chloropyridine C-nucleosides.
Kubelka, Tomáš; Slavětínská, Lenka; Eigner, Václav; Hocek, Michal; Organic & biomolecular chemistry 11 (2013) 4702–4718; doi:10.1039/c3ob40774h

data_7152977
_publ_section_title
;
 Synthesis of 2,6-disubstituted pyridin-3-yl C-2'-deoxyribonucleosides
 through chemoselective transformations of bromo-chloropyridine
 C-nucleosides.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4702
_journal_page_last               4718
_journal_paper_doi               10.1039/c3ob40774h
_journal_volume                  11
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H11 Br1 Cl1 N1 O3'
_chemical_formula_sum            'C10 H11 Br Cl N O3'
_chemical_formula_weight         308.56
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90.968(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.9755(9)
_cell_length_b                   6.9472(5)
_cell_length_c                   9.1777(9)
_cell_measurement_reflns_used    3239
_cell_measurement_temperature    170
_cell_measurement_theta_max      77.1283
_cell_measurement_theta_min      4.8152
_cell_volume                     572.19(9)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (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 0.996
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4296
_diffrn_reflns_theta_full        71.924
_diffrn_reflns_theta_max         77.338
_diffrn_reflns_theta_min         4.819
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.002
_exptl_absorpt_correction_T_max  0.23
_exptl_absorpt_correction_T_min  0.02
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.560
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.53
_refine_diff_density_min         -0.50
_refine_ls_abs_structure_details 'Flack (1983), 1039 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_coef       21.0(18)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0181
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2220
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.0005443
_refine_ls_shift/su_mean         0.0000442
_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:
11.5 -3.95 8.34
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0436
_refine_ls_wR_factor_gt          0.0423
_refine_ls_wR_factor_ref         0.0423
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                2220
_reflns_number_total             2333
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.44
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0358
_oxford_refine_ls_scale          9.06(2)
_oxford_reflns_number_all        2333
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            c3ob40774h.txt
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        'C10 H11 Br1 Cl1 N1 O3'
_cod_database_code               7152977
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S
CONT EXTPARAM
CONT ENANTIO
RIDE C ( 1,X'S) H ( 11,X'S)
RIDE C ( 2,X'S) H ( 21,X'S) H ( 22,X'S)
RIDE C ( 3,X'S) H ( 31,X'S)
RIDE C ( 4,X'S) H ( 41,X'S)
RIDE C ( 5,X'S) H ( 52,X'S) H ( 51,X'S)
RIDE O ( 7,X'S) H ( 71,X'S)
RIDE O ( 8,X'S) H ( 81,X'S)
RIDE C ( 13,X'S) H ( 131,X'S)
RIDE C ( 14,X'S) H ( 141,X'S)
END
;
_iucr_refine_instruction_details_restraints
;
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;