Carbocyclic Ribosylamines: Synthesis of 5-Substituted Carbocyclic β-Ribofuranosylamines
James T. Slama; Nimish Mehta; Ewa Skrzypczak-Jankun; Journal of Organic Chemistry 71 (2006) 7877–7880; doi:10.1021/jo060920l

data_4021975
_publ_contact_author
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     Dr. James T. Slama
     Department of Medicinal and Biological Chemistry
     University of Toledo, College of Pharmacy
     2801 W. Bancroft Street
     Toledo
     OH 43606-3390
     USA
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_publ_contact_author_email       jslama@utnet.utoledo.edu
_publ_contact_author_fax         '(419) 530-7946'
_publ_contact_author_phone       '(419) 530-1925'
_publ_section_title
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 Carbocyclic Ribosylamines: Synthesis of 5-Substituted
 Carbocyclic \b-Ribofuranosylamines
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7877
_journal_page_last               7880
_journal_paper_doi               10.1021/jo060920l
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C14 H20 Br N O5'
_chemical_formula_weight         362.22
_chemical_melting_point          163.3(3)
_chemical_name_systematic
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 (1S,4S,5R,6S,7S)-N-tert-butyloxycarbonyl-2-azabicyclo[2.2.1]heptan-7-bromo-5,6-
(dimethylmethylene)dioxy-3-one
;
_space_group_IT_number           145
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_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                120.00
_cell_formula_units_Z            12
_cell_length_a                   12.7298(2)
_cell_length_b                   12.7298(2)
_cell_length_c                   33.4904(8)
_cell_measurement_reflns_used    7754
_cell_measurement_temperature    173.0(10)
_cell_measurement_theta_max      29.14
_cell_measurement_theta_min      1.85
_cell_volume                     4699.96(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and the Toledo cifomatic'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(1)
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'PLATFORM (Bruker CCD 1K)'
_diffrn_measurement_method       '\w scans'
_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  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            32390
_diffrn_reflns_theta_full        29.14
_diffrn_reflns_theta_max         29.14
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    2.644
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.983
_exptl_crystal_colour            transparent
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2232
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(3)
_refine_ls_extinction_coef       0.00069(6)
_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   0.939
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     758
_refine_ls_number_reflns         12069
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0257
_refine_ls_shift/su_max          5.951
_refine_ls_shift/su_mean         0.067
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0226P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0476
_refine_ls_wR_factor_ref         0.0494
_reflns_number_gt                10357
_reflns_number_total             12069
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060920lsi20060504_011303.cif
_cod_depositor_comments
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The following automatic conversions were performed:

'_cell_measurement_temperature' value '173(1)K' was changed to
'173.0(10)' - the value should be numeric and without a unit
designator.

'_chemical_melting_point' value '163.1-163.6' was
changed to '163.3(3)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
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_cod_database_code               4021975