Modular and Practical Synthesis of 6-Substituted Pyridin-3-yl C-Nucleosides
Nicolas Joubert; Radek Pohl; Blanka Klepetářová; Michal Hocek; Journal of Organic Chemistry 72 (2007) 6797–6805; doi:10.1021/jo0709504

data_4024135
_publ_section_title
;
 Modular and Practical Synthesis of 6-Substituted Pyridin-3-yl C-Nucleosides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6797
_journal_page_last               6805
_journal_paper_doi               10.1021/jo0709504
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H12 Cl1 N1 O3'
_chemical_formula_sum            'C10 H12 Cl N O3'
_chemical_formula_weight         229.66
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             07-03-29
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 96.1275(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1887(1)
_cell_length_b                   7.5136(1)
_cell_length_c                   9.5782(1)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150
_cell_measurement_theta_max      77
_cell_measurement_theta_min      5
_cell_volume                     514.392(11)
_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      150
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.982
_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  0.036
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9510
_diffrn_reflns_theta_full        70.440
_diffrn_reflns_theta_max         77.406
_diffrn_reflns_theta_min         4.643
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.201
_exptl_absorpt_correction_T_max  0.64
_exptl_absorpt_correction_T_min  0.22
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.56
_refine_ls_abs_structure_details 'Flack (1983), 911 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.002(11)
_refine_ls_extinction_coef       40(2)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9217
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2053
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.000624
_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: 
 8.03 0.384 5.44 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0328
_refine_ls_wR_factor_gt          0.0327
_refine_ls_wR_factor_ref         0.0327
_reflns_limit_h_max              8
_reflns_limit_h_min              -9
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2053
_reflns_number_total             2070
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.09
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          15.85(3)
_oxford_structure_analysis_title 'ABS in P2(1)'
_cod_data_source_file            jo0709504-File003.cif
_cod_data_source_block           CRYSTALS_cif
_cod_depositor_comments
;
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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C10 H12 Cl1 N1 O3'
_cod_database_code               4024135