A General and Efficient Synthesis of Pyridin-2-yl C-Ribonucleosides Bearing Diverse Alkyl, Aryl, Amino, and Carbamoyl Groups in Position 6
Martin Štefko; Lenka Slavětínská; Blanka Klepetářová; Michal Hocek; Journal of Organic Chemistry 75 (2010) 442–449; doi:10.1021/jo902313g

data_4025172
_publ_section_title
;
 A General and Efficient Synthesis of Pyridin-2-yl C-Ribonucleosides
 Bearing Diverse Alkyl, Aryl, Amino, and Carbamoyl Groups in Position 6
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              442
_journal_page_last               449
_journal_paper_doi               10.1021/jo902313g
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H18 N2 O4'
_chemical_formula_sum            'C12 H18 N2 O4'
_chemical_formula_weight         254.29
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             09-10-21
_audit_creation_method           CRYSTALS_ver_12.87
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8208(3)
_cell_length_b                   9.0452(4)
_cell_length_c                   19.7411(9)
_cell_measurement_reflns_used    5770
_cell_measurement_temperature    150
_cell_measurement_theta_max      77
_cell_measurement_theta_min      4
_cell_volume                     1217.94(9)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Oxford Diffraction XCALIBUR'
_diffrn_measurement_device_type  Area
_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  0.044
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11567
_diffrn_reflns_theta_full        77.180
_diffrn_reflns_theta_max         77.180
_diffrn_reflns_theta_min         4.480
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.871
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.16
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       17(3)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0933
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.0002406
_refine_ls_shift/su_mean         0.0000294
_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: 
 7.14 -1.52 4.80 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0453
_refine_ls_wR_factor_gt          0.0419
_refine_ls_wR_factor_ref         0.0419
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                2201
_reflns_number_total             2580
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.40
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0364
_oxford_refine_ls_scale          6.766(15)
_oxford_reflns_number_all        2580
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_oxford_structure_analysis_title 'ABS in P2(1)2(1)2(1)'
_cod_data_source_file            jo902313g_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1217.93(10)
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4025172