One-Step Synthesis of Substituted Dihydro- and Tetrahydroisoquinolines by FeCl~3~.6H~2~O Catalyzed Intramolecular Friedel-Crafts Reaction of Benzylamino-Substituted Propargylic Alcohols
Wen Huang; Quansheng Shen; Jialiang Wang; Xigeng Zhou; Journal of Organic Chemistry 73 (2008) 1586–1589; doi:10.1021/jo702342r

data_4023292
_publ_section_title
;
 One-Step Synthesis of Substituted Dihydro- and
 Tetrahydroisoquinolines by FeCl~3~.6H~2~O
 Catalyzed Intramolecular Friedel-Crafts Reaction of
 Benzylamino-Substituted Propargylic Alcohols
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1586
_journal_page_last               1589
_journal_paper_doi               10.1021/jo702342r
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C31 H27 N O2 S'
_chemical_formula_weight         477.60
_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                 91.502(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.668(4)
_cell_length_b                   9.058(3)
_cell_length_c                   24.293(9)
_cell_measurement_reflns_used    945
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.806
_cell_measurement_theta_min      2.455
_cell_volume                     2566.7(17)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10432
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  0.9772
_exptl_absorpt_correction_T_min  0.9552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4492
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0491
_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^)+(0.0616P)^2^+0.3630P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1415
_reflns_number_gt                2845
_reflns_number_total             4492
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702342r-File002.cif
_cod_data_source_block           f70831b
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023292