A rapid synthesis of hexofuranose-like iminosugars using ring-closing metathesis.
Cren, Sylvaine; Wilson, Claire; Thomas, Neil R.; Organic letters 7 (2005) 3521–3523; doi:10.1021/ol051232b

data_1506643
_publ_contact_author             'Neil R. Thomas'
_publ_section_title
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 A rapid synthesis of hexofuranose-like iminosugars using ring-closing
 metathesis.
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_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              3521
_journal_page_last               3523
_journal_paper_doi               10.1021/ol051232b
_journal_volume                  7
_journal_year                    2005
_chemical_absolute_configuration syn
_chemical_formula_sum            'C14 H25 N O5'
_chemical_formula_weight         287.35
_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, except OH from delta-F'
_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            4
_cell_length_a                   6.2361(12)
_cell_length_b                   9.666(2)
_cell_length_c                   25.314(5)
_cell_measurement_reflns_used    4076
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.25
_cell_volume                     1525.9(5)
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2000)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_publication_material  'enCIFer(Allen et al.,2004);PLATON(Spek,2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       /w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7657
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.26
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS v2.05'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.44
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    'riding model, OH as rigid rotor'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.165
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0779P)^2^+0.5869P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1419
_reflns_number_gt                1850
_reflns_number_total             2025
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol051232bsi20050525_011438.cif
_cod_data_source_block           tbopyo
_cod_depositor_comments
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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_values 1715 2011-07-08 13:25:40Z adriana 
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_cod_database_code               1506643