Facile Synthesis of Azaspirocycles via Iron Trichloride-Promoted Cyclization/Chlorination of Cyclic 8-Aryl-5-aza-5-tosyl-2-en-7-yn-1-ols.
Yeh, Ming-Chang P; Fang, Cheng-Wei; Lin, Hsin-Hui; Organic letters 14 (2012) 1830–1833; doi:10.1021/ol300434m

data_1507583
_publ_section_title
;
 Facile Synthesis of Azaspirocycles via Iron Trichloride-Promoted
 Cyclization/Chlorination of Cyclic 8-Aryl-5-aza-5-tosyl-2-en-7-yn-1-ols.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1830
_journal_page_last               1833
_journal_paper_doi               10.1021/ol300434m
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C18 H21 Cl'
_chemical_formula_sum            'C18 H21 Cl'
_chemical_formula_weight         272.80
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 101.0880(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.9234(4)
_cell_length_b                   13.8004(5)
_cell_length_c                   22.4554(10)
_cell_measurement_reflns_used    7514
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.037
_cell_volume                     3017.8(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Denzo and Scalepack'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0753
_diffrn_reflns_av_sigmaI/netI    0.0720
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7150
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  1.089
_exptl_absorpt_correction_T_min  0.8401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 ?
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1143
_refine_ls_R_factor_gt           0.0561
_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^)+(0.0982P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1466
_refine_ls_wR_factor_ref         0.1865
_reflns_number_gt                1550
_reflns_number_total             2650
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300434m_si_006.cif
_cod_data_source_block           11940
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1507583