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_1505428
_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            'C21 H24 O4 S'
_chemical_formula_weight         372.46
_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                 103.06(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.738(16)
_cell_length_b                   10.632(18)
_cell_length_c                   19.29(3)
_cell_measurement_reflns_used    3398
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50.576
_cell_measurement_theta_min      4.402
_cell_volume                     1946(6)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.1495
_diffrn_reflns_av_sigmaI/netI    0.1056
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9856
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75023
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.497
_exptl_crystal_size_mid          0.458
_exptl_crystal_size_min          0.347
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       0.019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3613
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0674
_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          0.1526
_refine_ls_wR_factor_ref         0.1685
_reflns_number_gt                2567
_reflns_number_total             3613
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0709026si20070418_013704.cif
_cod_data_source_block           cd26362
_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_sg_symbol_H-M      P2(1)/n
_cod_database_code               1505428