Regio- and Stereoselective Glycosylation: Synthesis of 5-Haloimidazole α-Ribonucleosides
Tilak Chandra; Xiang Zou; Edward J. Valente; Kenneth L. Brown; Journal of Organic Chemistry 71 (2006) 5000–5003; doi:10.1021/jo060087s

data_4021755
_publ_section_title
;
 Regio- and Stereoselective Glycosylation: Synthesis of 5-Haloimidazole
 \a-Ribonucleosides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5000
_journal_page_last               5003
_journal_paper_doi               10.1021/jo060087s
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C30 H29 F1 N2 O4'
_chemical_formula_sum            'C30 H29 F N2 O4'
_chemical_formula_weight         500.55
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2005-12-08T12:34:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.058(4)
_cell_angle_beta                 89.990(4)
_cell_angle_gamma                89.935(4)
_cell_formula_units_Z            4
_cell_length_a                   8.2594(4)
_cell_length_b                   14.7704(8)
_cell_length_c                   20.8394(9)
_cell_measurement_reflns_used    20000
_cell_measurement_temperature    100
_cell_measurement_theta_max      40
_cell_measurement_theta_min      3
_cell_measurement_wavelength     0.71073
_cell_volume                     2542.3(2)
_computing_cell_refinement       'CrysAlis (Oxford Diffraction)'
_computing_data_collection       'CrysAlis (Oxford Diffraction)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction)'
_computing_molecular_graphics    'Molscript (Kraulis, 1991)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_UB_11      -0.016310928
_diffrn_orient_matrix_UB_12      0.0197615568
_diffrn_orient_matrix_UB_13      0.0305019585
_diffrn_orient_matrix_UB_21      0.0329075171
_diffrn_orient_matrix_UB_22      0.0418601946
_diffrn_orient_matrix_UB_23      -0.0109537185
_diffrn_orient_matrix_UB_31      -0.0780206911
_diffrn_orient_matrix_UB_32      0.0134014725
_diffrn_orient_matrix_UB_33      -0.0108540162
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            51661
_diffrn_reflns_theta_full        40.35
_diffrn_reflns_theta_max         40.35
_diffrn_reflns_theta_min         3.83
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        <2%
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.98319
_exptl_absorpt_correction_T_min  0.96252
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.28cycle7 beta (release 01-12-2005 CrysAlis171 .NET)
        (compiled Dec  1 2005,15:12:38)
Analytical numeric absorption correction using a multifaceted crystal
        model based on expressions derived by R.C. Clark & J.S. Reid.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     450
_refine_ls_number_reflns         15926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0639P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0953
_reflns_number_gt                13638
_reflns_number_total             15926
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060087ssi20060116_114311.cif
_cod_original_formula_sum        'C30 H29 F1 N2 O4'
_cod_database_code               4021755