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_1518136
_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         'C24 H28 N2 S'
_chemical_formula_sum            'C24 H28 N2 S'
_chemical_formula_weight         376.54
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 93.045(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.094(5)
_cell_length_b                   10.536(4)
_cell_length_c                   16.197(6)
_cell_measurement_temperature    100(2)
_cell_volume                     2060.9(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0738
_diffrn_reflns_av_sigmaI/netI    0.0767
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11272
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.168
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.947
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0523
_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^)+(0.0953P)^2^+1.7763P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1746
_reflns_number_gt                2991
_reflns_number_total             4039
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502871r_si_002.cif
_cod_data_source_block           8decc
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 1518134--1518136.cif.
;
_cod_original_cell_volume        2061.1(14)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1518136