Brønsted acid-mediated stereoselective cascade construction of functionalized tetrahydropyrans from 2-(arylmethylene)cyclopropylcarbinols and aldehydes.
Tian, Guo-Qiang; Shi, Min; Organic letters 9 (2007) 2405–2408; doi:10.1021/ol0709026

data_1505427
_publ_section_title
;
 Br\/onsted acid-mediated stereoselective cascade construction of
 functionalized tetrahydropyrans from
 2-(arylmethylene)cyclopropylcarbinols and aldehydes.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2405
_journal_page_last               2408
_journal_paper_doi               10.1021/ol0709026
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C19 H21 Br O5 S'
_chemical_formula_weight         441.33
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                80.479(5)
_cell_angle_beta                 83.302(5)
_cell_angle_gamma                79.666(6)
_cell_formula_units_Z            2
_cell_length_a                   5.7054(17)
_cell_length_b                   10.466(3)
_cell_length_c                   17.168(5)
_cell_measurement_reflns_used    981
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      40.292
_cell_measurement_theta_min      4.831
_cell_volume                     990.6(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_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  0.1459
_diffrn_reflns_av_sigmaI/netI    0.1822
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5804
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.21
_exptl_absorpt_coefficient_mu    2.206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43904
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.503
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.838
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.878
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4198
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.881
_refine_ls_R_factor_all          0.1395
_refine_ls_R_factor_gt           0.0730
_refine_ls_shift/su_max          0.189
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0881P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1809
_refine_ls_wR_factor_ref         0.2188
_reflns_number_gt                1861
_reflns_number_total             4198
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0709026si20070418_013650.cif
_cod_data_source_block           cd26340
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_sg_symbol_H-M      P-1
_cod_database_code               1505427