Elemental Sulfur-Incorporated Cyclizations of Pyrrolidines Leading to Thienopyrroles.
Yue, Yuanyuan; Shao, Huibin; Wang, Zhixian; Wang, Ke; Wang, Le; Zhuo, Kelei; Liu, Jianming; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01363

data_4038688
_publ_section_title
;
 Elemental Sulfur-Incorporated Cyclizations of Pyrrolidines Leading to
 Thienopyrroles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01363
_journal_year                    2020
_chemical_formula_sum            'C20 H17 N S'
_chemical_formula_weight         303.41
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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                 90.210(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4137(6)
_cell_length_b                   5.9329(2)
_cell_length_c                   20.1416(8)
_cell_measurement_reflns_used    3096
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.210
_cell_measurement_theta_min      3.9690
_cell_volume                     1602.90(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\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  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8879
_diffrn_reflns_theta_full        29.21
_diffrn_reflns_theta_max         29.21
_diffrn_reflns_theta_min         3.58
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.9786
_exptl_absorpt_correction_T_min  0.9163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3702
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0402P)^2^+0.6297P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1081
_reflns_number_gt                2901
_reflns_number_total             3702
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo0c01363_si_003.cif
_cod_data_source_block           shs-20180927
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4038688