Base-Mediated Hydroamination of Propargylamine: A Regioselective Intramolecular 5-exo-dig Cycloisomerization en Route to Imidazole-2-thione.
Ranjan, Alok; Yerande, Ragini; Wakchaure, Prasad B.; Yerande, Swapnil G.; Dethe, Dattatraya H.; Organic letters 16 (2014) 5788–5791; doi:10.1021/ol502871r

data_1518134
_publ_section_title
;
 Base-Mediated Hydroamination of Propargylamine: A Regioselective
 Intramolecular 5-exo-dig Cycloisomerization en Route to
 Imidazole-2-thione.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5788
_journal_page_last               5791
_journal_paper_doi               10.1021/ol502871r
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C28 H27 Cl N2 S'
_chemical_formula_weight         459.03
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 105.393(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.221(2)
_cell_length_b                   9.6494(8)
_cell_length_c                   12.1702(11)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      1.99
_cell_volume                     2402.7(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8472
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.99
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.9189
_exptl_absorpt_correction_T_min  0.8273
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3519
_refine_ls_number_restraints     89
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0291
_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^)+(0.0244P)^2^+0.8455P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0627
_reflns_number_gt                3275
_reflns_number_total             3519
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502871r_si_003.cif
_cod_data_source_block           2deca
_cod_depositor_comments
'Adding full bibliography for 1518134--1518136.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               1518134