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_4026599
_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 Br O'
_chemical_formula_sum            'C19 H19 Br O'
_chemical_formula_weight         343.25
_chemical_name_systematic
; 
(4S,4aS,10bR)-4-(4-bromophenyl)-2,4,4a,5,6,10b-hexahydro-1H-benzo[f]isochromene 
;
_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                98.0800(10)
_cell_angle_beta                 103.3820(10)
_cell_angle_gamma                106.8090(10)
_cell_formula_units_Z            4
_cell_length_a                   8.5484(7)
_cell_length_b                   11.9015(10)
_cell_length_c                   17.2138(14)
_cell_measurement_reflns_used    3865
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      21.57
_cell_measurement_theta_min      2.44
_cell_volume                     1590.0(2)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15300
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.25
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.582
_exptl_absorpt_correction_T_max  0.868
_exptl_absorpt_correction_T_min  0.721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SABABS; Bruker,2001'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.115
_refine_diff_density_min         -0.886
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5589
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0900P)^2^+0.8522P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1429
_refine_ls_wR_factor_ref         0.1726
_reflns_number_gt                3482
_reflns_number_total             5589
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo201027u_si_001_1.cif
_cod_data_source_block           aj31m
_cod_database_code               4026599