Mechanistic insights into the regiodivergent insertion of bicyclo[1.1.0]butanes towards carbocycle-tethered N-heteroarenes.
Erchinger, Johannes E.; Lenz, Madina; Mukherjee, Poulami; Li, Yan-Bo; Suresh, Adhya; Daniliuc, Constantin G.; Gutierrez, Osvaldo; Glorius, Frank; Chemical science 16 (2025) 4006–4013; doi:10.1039/d4sc08637f

data_1573782
_publ_section_title
;
 Mechanistic insights into the regiodivergent insertion of
 bicyclo[1.1.0]butanes towards carbocycle-tethered N-heteroarenes.
;
_journal_issue                   9
_journal_name_full               'Chemical science'
_journal_page_first              4006
_journal_page_last               4013
_journal_paper_doi               10.1039/d4sc08637f
_journal_volume                  16
_journal_year                    2025
_chemical_formula_sum            'C17 H15 N3 O S2'
_chemical_formula_weight         341.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           'APEX4 v2022.10-1'
_audit_update_record
;
2024-07-10 deposited with the CCDC.	2025-01-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.7580(4)
_cell_length_b                   7.7718(3)
_cell_length_c                   38.4713(17)
_cell_measurement_reflns_used    6252
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      27.1204
_cell_measurement_theta_min      2.1690
_cell_volume                     3216.5(2)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker APEX4 v2022.10-1 Photon III'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'SHELXT 2011/1 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            35150
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.12
_diffrn_source                   'Mo ImS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'micro focus tube'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.178
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.039
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.323
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0568P)^2^+0.6964P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1041
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2932
_reflns_number_total             3686
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc08637f2.cif
_cod_data_source_block           glo10599_9
_cod_depositor_comments
'Adding full bibliography for 1573780--1573782.cif.'
_cod_database_code               1573782
_shelx_res_checksum              2853