Tandem Prins/Friedel-Crafts Cyclization for Stereoselective Synthesis of Heterotricyclic Systems
B. V. Subba Reddy; Prashant Borkar; J. S. Yadav; B. Sridhar; René Grée; Journal of Organic Chemistry 76 (2011) 7677–7690; doi:10.1021/jo201027u

data_4026601
_publ_section_title
;
 Tandem Prins/Friedel-Crafts Cyclization for Stereoselective Synthesis of
 Heterotricyclic Systems
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7677
_journal_page_last               7690
_journal_paper_doi               10.1021/jo201027u
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C19 H19 F S'
_chemical_formula_sum            'C19 H19 F S'
_chemical_formula_weight         298.40
_chemical_name_systematic
; 
(4S,4aS,10bR)-4-(2-fluorophenyl)-2,4,4a,5,6,10b-hexahydro-1H-benzo
[f]isothiochromene 
;
_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                 116.270(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.988(2)
_cell_length_b                   9.8609(15)
_cell_length_c                   13.352(2)
_cell_measurement_reflns_used    5140
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      2.68
_cell_volume                     1533.4(4)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       '\w scan'
_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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14359
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.82
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0607P)^2^+0.3946P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1106
_reflns_number_gt                2246
_reflns_number_total             2701
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo201027u_si_001_3.cif
_cod_data_source_block           aj30
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4026601