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_4023291
_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
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_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            'C30 H25 N O2 S'
_chemical_formula_weight         463.57
_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                88.339(8)
_cell_angle_beta                 72.154(7)
_cell_angle_gamma                84.058(8)
_cell_formula_units_Z            2
_cell_length_a                   10.000(5)
_cell_length_b                   10.912(6)
_cell_length_c                   12.122(6)
_cell_measurement_reflns_used    580
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.247
_cell_measurement_theta_min      2.329
_cell_volume                     1252.2(11)
_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 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0863
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5782
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_correction_T_min  0.9695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sheet
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.899
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.899
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0562
_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^)+(0.0962P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1761
_reflns_number_gt                2615
_reflns_number_total             4822
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702342r-File001.cif
_cod_data_source_block           f70522b
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 
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_cod_database_code               4023291