Amine-promoted three-component cycloaddition of bicyclo[1.1.0]butanes with hydroxylamine and polyformaldehyde: expedient access to 2-oxa-3-azabicyclo[3.1.1]heptanes
Zhu, Yu; Lv, Xueli; Hong, Jun; Wu, Shengxing; Li, Zhi; Wang, Minyan; Jiang, Xinpeng; Green Chemistry 27 (2025) 2464–2470; doi:10.1039/D4GC05355A

data_7249812
_publ_section_title
;
 Amine-promoted three-component cycloaddition of bicyclo[1.1.0]butanes
 with hydroxylamine and polyformaldehyde: expedient access to
 2-oxa-3-azabicyclo[3.1.1]heptanes
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              2464
_journal_page_last               2470
_journal_paper_doi               10.1039/D4GC05355A
_journal_volume                  27
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H24 N2 O3'
_chemical_formula_sum            'C22 H24 N2 O3'
_chemical_formula_weight         364.43
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-26
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-06-25 deposited with the CCDC.	2025-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2419(4)
_cell_length_b                   12.3869(5)
_cell_length_c                   13.4125(6)
_cell_measurement_reflns_used    9127
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.394
_cell_measurement_theta_min      3.421
_cell_volume                     1867.72(13)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            61419
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.660
_diffrn_reflns_theta_min         4.227
_diffrn_source_current           3.57
_diffrn_source_power             0.24957869999999996
_diffrn_source_voltage           69.91
_exptl_absorpt_coefficient_mu    0.443
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1322 before and 0.0664 after correction.
The Ratio of minimum to maximum transmission is 0.9120.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1922 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4289
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0305
_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^)+(0.0474P)^2^+0.2107P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0790
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4138
_reflns_number_total             4289
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc05355a2.cif
_cod_data_source_block           240325_zy_6_142
_cod_depositor_comments
'Adding full bibliography for 7249811--7249812.cif.'
_cod_database_code               7249812
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 O1-N1 \\sim O1-N1A
 with sigma of 0.02
 C7-N1 \\sim C7-N1A
 with sigma of 0.02
 C6-N1 \\sim C6-N1A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N1 \\sim N1A \\sim C6: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
4. Others
 Sof(N1A)=Sof(H7BC)=Sof(H7BD)=1-FVAR(1)
 Sof(N1)=Sof(H7AA)=Sof(H7AB)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C7(H7AA,H7AB), C7(H7BC,H7BD), C9(H9A,H9B), C11(H11A,H11B), C13(H13A,H13B),
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
;
_olex2_submission_special_instructions 'No special instructions were received'