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_4023058
_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         'C14 H19 I N2 O7'
_chemical_formula_sum            'C14 H19 I N2 O7'
_chemical_formula_weight         454.21
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.1672(3)
_cell_length_b                   13.4581(6)
_cell_length_c                   31.8730(12)
_cell_measurement_reflns_used    3665
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.89
_cell_measurement_theta_min      2.80
_cell_volume                     3503.3(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 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0970
_diffrn_reflns_av_sigmaI/netI    0.1015
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            30717
_diffrn_reflns_theta_full        26.55
_diffrn_reflns_theta_max         26.55
_diffrn_reflns_theta_min         2.92
_diffrn_standards_number         'no decay'
_exptl_absorpt_coefficient_mu    1.866
_exptl_absorpt_correction_T_max  0.9125
_exptl_absorpt_correction_T_min  0.8963
_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    1.722
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.498
_refine_diff_density_min         -0.880
_refine_diff_density_rms         0.139
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         7202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0531
_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^)+(0.0515P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1126
_reflns_number_gt                5219
_reflns_number_total             7202
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701608p-File006.cif
_cod_data_source_block           37
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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_database_code               4023058