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_7152967
_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         'C11 H14 Cl1 N1 O3'
_chemical_formula_sum            'C11 H14 Cl N O3'
_chemical_formula_weight         243.69
_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                 96.676(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3111(3)
_cell_length_b                   11.1077(6)
_cell_length_c                   19.5383(13)
_cell_measurement_reflns_used    5945
_cell_measurement_temperature    190
_cell_measurement_theta_max      77
_cell_measurement_theta_min      5
_cell_volume                     1144.83(12)
_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_pressure         101
_diffrn_ambient_temperature      190
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.982
_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  0.026
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10498
_diffrn_reflns_theta_full        73.534
_diffrn_reflns_theta_max         77.404
_diffrn_reflns_theta_min         4.557
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.908
_exptl_absorpt_correction_T_max  0.47
_exptl_absorpt_correction_T_min  0.24
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.53
_refine_diff_density_min         -0.45
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.008(12)
_refine_ls_extinction_coef       72.2(20)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0397
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4688
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.0004146
_refine_ls_shift/su_mean         0.0000500
_refine_ls_structure_factor_coef Fsqd
_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: 
 0.132E+04 0.215E+04 0.120E+04 416. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0950
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0950
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              14
_reflns_limit_k_min              -13
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                4585
_reflns_number_total             4688
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.24
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0383
_oxford_refine_ls_scale          7.21(18)
_oxford_reflns_number_all        4688
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            c3ob40774h_2.cif
_cod_data_source_block           1
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1144.84(12)
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        'C11 H14 Cl1 N1 O3'
_cod_database_code               7152967
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
CONT ENANTIO 
RIDE C   ( 1a',X'S) H   (1a'1,X'S) 
RIDE C   ( 2a',X'S) H   (2a'2,X'S) H   (2a'1,X'S) 
RIDE C   ( 3a',X'S) H   (3a'1,X'S) 
RIDE C   ( 4a',X'S) H   (4a'1,X'S) 
RIDE C   ( 5a',X'S) H   (5a'2,X'S) H   (5a'1,X'S) 
RIDE O   ( 7a',X'S) H   (7a'1,X'S) 
RIDE O   ( 8a',X'S) H   (8a'1,X'S) 
RIDE C   ( 4a,X'S) H   (4a1,X'S) 
RIDE C   ( 5a,X'S) H   (5a1,X'S) 
RIDE C   ( 7a,X'S) H   (7a1,X'S) H   (7a2,X'S) H   (7a3,X'S) 
RIDE C   ( 1b',X'S) H   (1b'1,X'S) 
RIDE C   ( 2b',X'S) H   (2b'1,X'S) H   (2b'2,X'S) 
RIDE C   ( 3b',X'S) H   (3b'1,X'S) 
RIDE C   ( 4b',X'S) H   (4b'1,X'S) 
RIDE C   ( 5b',X'S) H   (5b'1,X'S) H   (5b'2,X'S) 
RIDE O   ( 7b',X'S) H   (7b'1,X'S) 
RIDE O   ( 8b',X'S) H   (8b'1,X'S) 
RIDE C   ( 4b,X'S) H   (4b1,X'S) 
RIDE C   ( 5b,X'S) H   (5b1,X'S) 
RIDE C   ( 7b,X'S) H   (7b3,X'S) H   (7b2,X'S) H   (7b1,X'S) 
END                                                                             
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_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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