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_1507579
_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         'C23 H24 Cl N O2 S'
_chemical_formula_sum            'C23 H24 Cl N O2 S'
_chemical_formula_weight         413.94
_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                 108.705(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5931(2)
_cell_length_b                   38.1706(13)
_cell_length_c                   8.8048(3)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     2098.80(12)
_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      200(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13847
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.07
_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_T_max  0.9315
_exptl_absorpt_correction_T_min  0.8197
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0684P)^2^+0.7351P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1256
_reflns_number_gt                3280
_reflns_number_total             3664
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300434m_si_002.cif
_cod_data_source_block           a10653
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1507579