Enantioselective dearomative formal (3+3) cycloadditions of bicyclobutanes with aromatic azomethine imines: access to fused 2,3-diazabicyclo[3.1.1]heptanes.
Yang, Xue-Chun; Wu, Feng; Wu, Wen-Biao; Zhang, Xu; Feng, Jian-Jun; Chemical science 15 (2024) 19488–19495; doi:10.1039/d4sc06334a

data_1573075
_publ_section_title
;
 Enantioselective dearomative formal (3+3) cycloadditions of
 bicyclobutanes with aromatic azomethine imines: access to fused
 2,3-diazabicyclo[3.1.1]heptanes.
;
_journal_issue                   46
_journal_name_full               'Chemical science'
_journal_page_first              19488
_journal_page_last               19495
_journal_paper_doi               10.1039/d4sc06334a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C31 H26 Br N4 O2'
_chemical_formula_sum            'C31 H25 Br N4 O2'
_chemical_formula_weight         565.46
_chemical_name_systematic
(4-benzoyl-11-bromo-3-phenyl-3,4-dihydro-2H-1,3-methanopyridazino[6,1-a]isoquinolin-1(11bH)-yl)(1-methyl-1H-imidazol-2-yl)methanone
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-14
_audit_creation_method
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Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_audit_update_record
;
2024-08-02 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                102.9960(10)
_cell_angle_beta                 101.6570(10)
_cell_angle_gamma                114.4520(10)
_cell_formula_units_Z            2
_cell_length_a                   9.8157(2)
_cell_length_b                   11.2682(3)
_cell_length_c                   14.0489(4)
_cell_measurement_reflns_used    8009
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      68.118
_cell_measurement_theta_min      2.331
_cell_volume                     1299.74(6)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APX-II'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            47937
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.224
_diffrn_reflns_theta_min         3.424
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.447
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_correction_T_min  0.0735
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       needle
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.134
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.058
_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     344
_refine_ls_number_reflns         4746
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0242
_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^)+(0.0248P)^2^+1.0267P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0626
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4670
_reflns_number_total             4746
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc06334a2.cif
_cod_data_source_block           cu_2024051101_0m
_cod_depositor_comments
'Adding full bibliography for 1573075--1573076.cif.'
_cod_database_code               1573075
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.894
_shelx_estimated_absorpt_t_min   0.735
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C2(H2), C16(H16), C3(H3), C14(H14), C12(H12), C15(H15), C4(H4A),
 C27(H27), C21(H21), C20(H20), C31(H31), C28(H28), C5(H5), C29(H29), C6(H6),
 C13(H13), C30(H30)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              16459
_shelx_hkl_checksum              5531
_olex2_submission_special_instructions 'No special instructions were received'