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_1518135
_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_moiety         'C29 H38 N2 O'
_chemical_formula_sum            'C29 H38 N2 O'
_chemical_formula_weight         430.61
_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                89.647(5)
_cell_angle_beta                 89.551(5)
_cell_angle_gamma                84.285(5)
_cell_formula_units_Z            2
_cell_length_a                   5.394(5)
_cell_length_b                   14.787(5)
_cell_length_c                   15.397(5)
_cell_measurement_reflns_used    1249
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      4.12
_cell_volume                     1221.9(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'DIAMOND 3.1 d'
_computing_publication_material  'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0715
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6002
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         4.12
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.288419
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'North et al, 1968'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             468.0
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4209
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0640
_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^)+(0.0999P)^2^+0.3350P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1631
_refine_ls_wR_factor_ref         0.1980
_reflns_number_gt                2947
_reflns_number_total             4209
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502871r_si_001.cif
_cod_data_source_block           21novbm
_cod_depositor_comments
'Adding full bibliography for 1518134--1518136.cif.'
_cod_database_code               1518135