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_4021503
_publ_contact_author
;
    Dr. Benet-Buchholz, Jordi
    Institut Catal\`a d'Investigaci\'o Qu\'imica    
    X-ray Diffraction Unit
    Avgda. Pa\"isos Catalans s/n
    E-43007 Tarragona
    Spain
;
_publ_contact_author_email       jbenet@iciq.es
_publ_contact_author_fax         '+34 977 920 221'
_publ_contact_author_phone       '+34 977 920 204'
_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_formula_sum            'C18 H20 O4'
_chemical_formula_weight         300.34
_chemical_name_common
;
 Benzo[c]oxepin
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 99.434(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.8358(16)
_cell_length_b                   5.6888(6)
_cell_length_c                   17.707(2)
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max
;
 Slow evaporation of ethanol at room temperature
;
_cell_volume                     1474.2(3)
_computing_cell_refinement       'Bruker SAINT program Vers. 5.0'
_computing_data_collection       'Bruker SMART CCD area detector system'
_computing_data_reduction        'Bruker SAINT program Vers. 5.0'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            'Smart 1000 CCD area detector'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'four-circle diffractometer Bruker P4'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans,
 in omega at 0.3 deg scan width, three runs with 98, 67 and 67 frames, phi=0 deg
 in phi at 0.3 deg scan width, two runs with 1207 frames, omega=-32 deg
;
_diffrn_measurement_specimen_support
'magnetic support whith 10 micron nylon fiber cryoloop'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0848
_diffrn_reflns_av_sigmaI/netI    0.0792
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21142
_diffrn_reflns_theta_full        31.00
_diffrn_reflns_theta_max         31.00
_diffrn_reflns_theta_min         1.66
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_current           240
_diffrn_source_power             45
_diffrn_source_size              '10 mm x 0.5 mm fine focus'
_diffrn_source_type              'MACScience Co. M18X-HF'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.766391
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 Siemens SADABS program multi-scan
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.006
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4598
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.911
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0527
_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^)+(0.0627P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1239
_reflns_number_gt                2765
_reflns_number_total             4598
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo052208esi20051025_100454.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/n'
_cod_database_code               4021503