Boron Trifluoride-Induced, New Stereospecific Rearrangements of Chiral Epoxy Ethers. Ready Access to Enantiopure 4-(Diarylmethyl)-1,3-dioxolanes and 4,5-Disubstituted Tetrahydrobenzo[c]oxepin-4-ols
Gabriela Islas-González; Jordi Benet-Buchholz; Miguel A. Maestro; Antoni Riera; Miquel A. Pericàs; Journal of Organic Chemistry 71 (2006) 1537–1544; doi:10.1021/jo052208e

data_4021502
_publ_contact_author
;
    Maestro, Miguel A.
    Facultade de Ciencias    
    Universidade da Coru\~na
    E-15071 A Coru\~na
    Spain
;
_publ_contact_author_email       qfmaestr@udc.es
_publ_section_title
;
 Boron Trifluoride-Induced, New Stereospecific Rearrangements of
 Chiral Epoxy Ethers. Ready Access to Enantiopure
 4-(Diarylmethyl)-1,3-dioxolanes and 4,5-Disubstituted
 Tetrahydrobenzo[c]oxepin-4-ols
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1537
_journal_page_last               1544
_journal_paper_doi               10.1021/jo052208e
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_formula_sum            'C30 H29 N O6 S2'
_chemical_formula_weight         563.66
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 93.167(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3773(9)
_cell_length_b                   28.293(3)
_cell_length_c                   10.4971(11)
_cell_measurement_reflns_used    4508
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.34
_cell_measurement_theta_min      2.18
_cell_volume                     2780.8(5)
_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'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17604
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.9791
_exptl_absorpt_correction_T_min  0.8911
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     717
_refine_ls_number_reflns         10675
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.1369
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0403P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.1067
_reflns_number_gt                5584
_reflns_number_total             10675
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo052208esi20051025_100433.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21'
_cod_database_code               4021502