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_1573781
_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 H18 N2 O2 S'
_chemical_formula_weight         314.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                 95.8740(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.75790(10)
_cell_length_b                   16.2633(4)
_cell_length_c                   16.7223(4)
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.6561
_cell_measurement_theta_min      3.8011
_cell_volume                     1557.70(6)
_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, 2019)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28260
_diffrn_reflns_theta_full        66.74
_diffrn_reflns_theta_max         66.74
_diffrn_reflns_theta_min         3.80
_diffrn_source                   'Cu 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    1.917
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.74
_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    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.260
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         2755
_refine_ls_number_restraints     173
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0321
_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^)+(0.0304P)^2^+1.2152P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0796
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2397
_reflns_number_total             2755
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc08637f2.cif
_cod_data_source_block           glo10601_4aj-minor_regioisomer
_cod_depositor_comments
'Adding full bibliography for 1573780--1573782.cif.'
_cod_database_code               1573781
_shelx_res_checksum              79206