Switching of regioselectivity in base-mediated diastereoselective annulation of 2,3-epoxy tosylates and their N-tosylaziridine analogs with 2-mercaptobenzimidazole.
Das, Arup Jyoti; Borgohain, Hemi; Sarma, Bipul; Das, Sajal Kumar; Organic & biomolecular chemistry 18 (2020) 441–449; doi:10.1039/c9ob02454a

data_7157250
_publ_section_title
;
 Switching of regioselectivity in base-mediated diastereoselective
 annulation of 2,3-epoxy tosylates and their N-tosylaziridine analogs with
 2-mercaptobenzimidazole.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              441
_journal_page_last               449
_journal_paper_doi               10.1039/c9ob02454a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C13 H16 N2 O S'
_chemical_formula_weight         248.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-12-11 deposited with the CCDC.	2019-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.914(3)
_cell_length_b                   12.666(5)
_cell_length_c                   10.006(3)
_cell_measurement_reflns_used    629
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      12.30
_cell_measurement_theta_min      2.59
_cell_volume                     1256.5(7)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2530
_diffrn_reflns_av_unetI/netI     0.1509
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            36233
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.922
_diffrn_reflns_theta_min         2.594
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.06(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3217
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.2005
_refine_ls_R_factor_gt           0.0627
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1233
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                1288
_reflns_number_total             3217
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02454a2.cif
_cod_data_source_block           newad328
_cod_depositor_comments
'Adding full bibliography for 7157250--7157253.cif.'
_cod_database_code               7157250
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.928
_shelx_estimated_absorpt_t_max   0.964
_exptl_absorpt_special_details   SADABS
_shelx_res_checksum              92233