Stereoselective Synthesis of Hexahydro-1H-pyrano- and thiopyrano[3,4-c]quinoline Derivatives through a Prins Cascade Cyclization
B.V. Subba Reddy; Durgaprasad Medaboina; B. Sridhar; Kiran Kumar Singarapu; Journal of Organic Chemistry 78 (2013) 8161–8168; doi:10.1021/jo4009657

data_4028489
_publ_section_title
;
 Stereoselective Synthesis of Hexahydro-1H-pyrano- and
 thiopyrano[3,4-c]quinoline Derivatives through a Prins Cascade
 Cyclization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8161
_journal_page_last               8168
_journal_paper_doi               10.1021/jo4009657
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C25 H23 Br F N O3 S'
_chemical_formula_sum            'C25 H23 Br F N O3 S'
_chemical_formula_weight         516.41
_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                 104.966(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9448(6)
_cell_length_b                   15.4733(9)
_cell_length_c                   13.8810(8)
_cell_measurement_reflns_used    9379
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.83
_cell_measurement_theta_min      2.33
_cell_volume                     2271.0(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 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  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21365
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.938
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_description       needle
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.053
_refine_diff_density_min         -0.817
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3996
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0481P)^2^+1.6171P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1010
_reflns_number_gt                3350
_reflns_number_total             3996
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo4009657_si_001.cif
_cod_data_source_block           ao45
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4028489