Cycloaddition of bicyclo[1.1.0]butanes with enamides for the efficient synthesis of 2-amino-bicyclo[2.1.1]hexanes.
Zhu, Yanren; Yang, Shaoxiong; Chen, Huiyu; Zhang, Fang; Pu, Enfan; Jiang, Piaopiao; Jin, Yi; Zhang, Hongbin; Chen, Jingbo; Chemical communications (Cambridge, England) 61 (2025) 11493–11496; doi:10.1039/d5cc02908b

data_7134767
_publ_section_title
;
 Cycloaddition of bicyclo[1.1.0]butanes with enamides for the efficient
 synthesis of 2-amino-bicyclo[2.1.1]hexanes.
;
_journal_issue                   61
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11493
_journal_page_last               11496
_journal_paper_doi               10.1039/d5cc02908b
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C22 H17 Br N O3'
_chemical_formula_sum            'C22 H17 Br N O3'
_chemical_formula_weight         423.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2025-01-13
_audit_creation_method
;
FinalCif V89 by Daniel Kratzert, Freiburg 2025,
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2025-02-22 deposited with the CCDC.	2025-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.271(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.4907(3)
_cell_length_b                   15.9278(7)
_cell_length_c                   7.9606(5)
_cell_measurement_reflns_used    8338
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.61
_cell_volume                     931.46(8)
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.15
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10558
_diffrn_reflns_point_group_measured_fraction_full 0.876
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_min         2.558
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.229
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1575 before and 0.0811 after correction.
The Ratio of minimum to maximum transmission is 0.8114.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_description       plate
_exptl_crystal_F_000             430
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.489
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.068(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3685
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0367P)^2^+1.2286P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0948
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_full    0.744
_reflns_Friedel_fraction_max     0.710
_reflns_number_gt                3488
_reflns_number_total             3685
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02908b2.cif
_cod_data_source_block           1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7134766--7134767.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7134767
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.932(15)
 0.068(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Riding coordinates:
 O1(H1), N1(H1A)
3.b Ternary CH refined with riding coordinates:
 C7(H7), C12(H12)
3.c Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
3.d Aromatic/amide H refined with riding coordinates:
 C1(H1B), C2(H2), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17), C18(H18)
3.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_shelx_res_checksum              41301
_shelx_hkl_checksum              9158