One-Pot Synthesis of Acyclic Nucleosides from Carbohydrate Derivatives, by Combination of Tandem and Sequential Reactions
Alicia Boto; Dácil Hernández; Rosendo Hernández; Eleuterio Álvarez; Journal of Organic Chemistry 72 (2007) 9523–9532; doi:10.1021/jo701608p

data_4023056
_publ_section_title
;
 One-Pot Synthesis of Acyclic Nucleosides from Carbohydrate
 Derivatives, by Combination of Tandem and Sequential Reactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9523
_journal_page_last               9532
_journal_paper_doi               10.1021/jo701608p
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration rmad
_chemical_formula_moiety         '4(C14 H19 I N2 O7), C4 H8 O2'
_chemical_formula_sum            'C60 H84 I4 N8 O30'
_chemical_formula_weight         1904.95
_chemical_name_systematic
; 
 ? 
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.521(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.839(3)
_cell_length_b                   19.750(7)
_cell_length_c                   22.287(7)
_cell_measurement_reflns_used    2837
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      17.89
_cell_measurement_theta_min      2.77
_cell_volume                     3857(2)
_computing_cell_refinement       'SAINT+ v. 7.06 a (Bruker AXS, 2003)'
_computing_data_collection       'APEX-W2K-NT v. 1.0 (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT+ v. 7.06 a (Bruker AXS, 2001)'
_computing_molecular_graphics    'XP, SHELXTL v. 6.10 (Bruker, 2000)'
_computing_publication_material  'XCIF, SHELXTL v. 6.12 (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker-Nonius X8kappa APEX II CCD system'
_diffrn_measurement_method       '\w rotations with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_av_sigmaI/netI    0.1398
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            50355
_diffrn_reflns_theta_full        26.46
_diffrn_reflns_theta_max         26.46
_diffrn_reflns_theta_min         1.84
_diffrn_standards_number         'no decay'
_exptl_absorpt_coefficient_mu    1.700
_exptl_absorpt_correction_T_max  0.9004
_exptl_absorpt_correction_T_min  0.8538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS: Area-Detector Absorption Correction. Bruker-AXS 
 within SAINT+ package, v. 6.22 (2001). 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.344
_refine_diff_density_min         -1.038
_refine_diff_density_rms         0.241
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_coef       0.0087(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     920
_refine_ls_number_reflns         14747
_refine_ls_number_restraints     865
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.1970
_refine_ls_R_factor_gt           0.0873
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0967P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1893
_refine_ls_wR_factor_ref         0.2360
_reflns_number_gt                7042
_reflns_number_total             14747
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701608p-File004.cif
_cod_data_source_block           36
_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_database_code               4023056