One-Pot, Three-Component Synthesis of 5-Sulfenyl-2-iminothiazolines by Cross-Dehydrogenative C-S Coupling Using I~2~/DMSO in Open Air
Bodhak, Chandan; Pramanik, Animesh; The Journal of Organic Chemistry 84 (2019) 7265–7278; doi:10.1021/acs.joc.9b00785

data_4034585
_publ_section_title
;
 One-Pot, Three-Component Synthesis of 5-Sulfenyl-2-iminothiazolines by
 Cross-Dehydrogenative C-S Coupling Using I~2~/DMSO in Open Air
;
_journal_coden_ASTM              JOCEAH
_journal_issue                   11
_journal_name_full               'The Journal of Organic Chemistry'
_journal_page_first              7265
_journal_page_last               7278
_journal_paper_doi               10.1021/acs.joc.9b00785
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C25 H21 Br N2 O S2'
_chemical_formula_weight         508.46
_chemical_name_systematic
;
 (Z)-5-((4-Bromophenyl)thio)-3-cyclopropyl-4-(4-methoxyphenyl)-N-phenylthiazol-2(3H)-imine 
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_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                 102.582(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.834(3)
_cell_length_b                   23.521(6)
_cell_length_c                   10.229(3)
_cell_measurement_reflns_used    5595
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.21
_cell_measurement_theta_min      2.22
_cell_volume                     2309.2(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15869
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    1.981
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Hexagonal
_exptl_crystal_F_000             1036
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0395P)^2^+1.0137P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0845
_reflns_number_gt                3211
_reflns_number_total             4065
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b00785_si_002.cif
_cod_data_source_block           cb1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        2309.1(11)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_original_formula_sum        'C25 H20 Br N2 O S2'
_cod_database_code               4034585