Diastereoselective 1,3-nitrooxygenation of bicyclo[1.1.0]butanes
Maity, Anirban; Balanna, Kuruva; Daniliuc, Constantin G.; Studer, Armido; Chemical Science 16 (2025) 7264–7269; doi:10.1039/D4SC08753D

data_1574219
_publ_section_title
;
 Diastereoselective 1,3-nitrooxygenation of bicyclo[1.1.0]butanes
;
_journal_issue                   17
_journal_name_full               'Chemical Science'
_journal_page_first              7264
_journal_page_last               7269
_journal_paper_doi               10.1039/D4SC08753D
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H30 N2 O4'
_chemical_formula_weight         410.50
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           'APEX4 v2022.10-1'
_audit_update_record
;
2024-12-18 deposited with the CCDC.	2025-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4366(2)
_cell_length_b                   11.2441(2)
_cell_length_c                   22.9481(5)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.5672
_cell_measurement_theta_min      3.8525
_cell_volume                     2176.90(8)
_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 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0439
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            22885
_diffrn_reflns_theta_full        66.65
_diffrn_reflns_theta_max         66.65
_diffrn_reflns_theta_min         3.85
_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    0.687
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.84
_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    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.063
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.139
_refine_ls_abs_structure_details
;

Flack x determined using 1491 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3797
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0291
_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^)+(0.0302P)^2^+0.4672P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0699
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3598
_reflns_number_total             3797
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc08753d2.cif
_cod_data_source_block           stu10640_2
_cod_depositor_comments          'Adding full bibliography for 1574219.cif.'
_cod_database_code               1574219
_shelx_res_checksum              53639