A Vicarious One-Pot Transformation of a Fluorocyclitol to a Polycyclitol: Observation of a Formal 4-Fold Axial-Equatorial Epimerization on a Conformationally Locked Scaffold
Goverdhan Mehta; Saikat Sen; Journal of Organic Chemistry 75 (2010) 8287–8290; doi:10.1021/jo101660x

data_4025843
_publ_contact_author_address
;
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012
;
_publ_contact_author_email       gm@orgchem.iisc.ernet.in
_publ_contact_author_fax         +91-80-23600936
_publ_contact_author_name
;
Prof. Goverdhan Mehta
;
_publ_contact_author_phone       +91-80-22932850
_publ_section_title
;
 A Vicarious One-Pot Transformation of a Fluorocyclitol to a Polycyclitol:
 Observation of a Formal 4-Fold Axial-Equatorial Epimerization on a
 Conformationally Locked Scaffold
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8287
_journal_page_last               8290
_journal_paper_doi               10.1021/jo101660x
_journal_volume                  75
_journal_year                    2010
_chemical_compound_source        'see text'
_chemical_formula_iupac          'C10 H18 O6'
_chemical_formula_moiety         'C10 H18 O6'
_chemical_formula_structural     'C10 H18 O6'
_chemical_formula_sum            'C10 H18 O6'
_chemical_formula_weight         234.24
_chemical_name_systematic
;
perhydro-2,3,4a,6,7,8a-naphthalenehexol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             'Aug 16 00:05:34 2010'
_audit_creation_method           'PLATON <TABLE ACC> option'
_audit_update_record
;
2010-08-19 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 91.556(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.8081(6)
_cell_length_b                   10.9082(10)
_cell_length_c                   8.2899(8)
_cell_measurement_reflns_used    1018
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      3.09
_cell_volume                     525.02(9)
_computing_cell_refinement       'SMART (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker AXS SMART APEX CCD area-detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3571
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.90
_diffrn_reflns_theta_min         3.51
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_correction_T_min  0.9712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         1026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0681P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1102
_reflns_number_gt                733
_reflns_number_total             1026
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo101660x_si_001.cif
_cod_data_source_block           tetraequatorial_hexol_2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4025843