Highly stereoselective prins cyclization of (Z)- and (E)-gamma-brominated homoallylic alcohols to 2,4,5,6-tetrasubstituted tetrahydropyrans.
Liu, Feng; Loh, Teck-Peng; Organic letters 9 (2007) 2063–2066; doi:10.1021/ol070506n

data_1505388
_publ_section_title
;
 Highly stereoselective prins cyclization of (Z)- and (E)-gamma-brominated
 homoallylic alcohols to 2,4,5,6-tetrasubstituted tetrahydropyrans.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2063
_journal_page_last               2066
_journal_paper_doi               10.1021/ol070506n
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C19 H26 Br2 O'
_chemical_formula_weight         430.22
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.932(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4511(4)
_cell_length_b                   18.9558(7)
_cell_length_c                   9.7638(4)
_cell_measurement_reflns_used    7660
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      30.19
_cell_measurement_theta_min      2.29
_cell_volume                     1860.00(13)
_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      273(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23668
_diffrn_reflns_theta_full        30.55
_diffrn_reflns_theta_max         30.55
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    4.359
_exptl_absorpt_correction_T_max  0.4760
_exptl_absorpt_correction_T_min  0.2745
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         5664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0264
_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^)+(0.0241P)^2^+0.7700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0553
_refine_ls_wR_factor_ref         0.0599
_reflns_number_gt                4417
_reflns_number_total             5664
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol070506nsi20070228_070731.cif
_cod_data_source_block           ltp19m
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1860.00(12)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1505388