Diastereoselective dearomative cycloaddition of bicyclobutanes with pyridinium ylides: a modular approach to multisubstituted azabicyclo[3.1.1]heptanes.
Dhake, Kushal; Woelk, Kyla J.; Krueckl, Liam D. N.; Alberts, Faith; Mutter, James; Pohl, Matthew O.; Thomas, Gilian T.; Sharma, Muskan; Bjornerud-Brown, Jaelyn; Fernández, Nahiane Pipaón; Schley, Nathan D.; Leitch, David C.; Chemical communications (Cambridge, England) 60 (2024) 13008–13011; doi:10.1039/d4cc04730c

data_7133839
_publ_section_title
;
 Diastereoselective dearomative cycloaddition of bicyclobutanes with
 pyridinium ylides: a modular approach to multisubstituted
 azabicyclo[3.1.1]heptanes.
;
_journal_issue                   89
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13008
_journal_page_last               13011
_journal_paper_doi               10.1039/d4cc04730c
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C20 H23 N O4'
_chemical_formula_sum            'C20 H23 N O4'
_chemical_formula_weight         341.39
_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             2024-07-29
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-07-30 deposited with the CCDC.	2024-10-08 downloaded from the CCDC.
;
_cell_angle_alpha                75.0940(10)
_cell_angle_beta                 88.4840(10)
_cell_angle_gamma                89.5780(10)
_cell_formula_units_Z            2
_cell_length_a                   5.8883(2)
_cell_length_b                   10.8918(3)
_cell_length_c                   14.0443(4)
_cell_measurement_reflns_used    9929
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.37
_cell_measurement_theta_min      3.26
_cell_volume                     870.10(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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_temperature      100
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18254
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.415
_diffrn_reflns_theta_min         3.257
_diffrn_source_current           0.59
_diffrn_source_power             0.026373
_diffrn_source_voltage           44.7
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0823 before and 0.0497 after correction.
The Ratio of minimum to maximum transmission is 0.8918.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       irregular
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0449P)^2^+0.4366P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0959
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2899
_reflns_number_total             3161
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04730c2.cif
_cod_data_source_block           leitch001
_cod_depositor_comments
'Adding full bibliography for 7133838--7133839.cif.'
_cod_original_cell_volume        870.11(5)
_cod_database_code               7133839
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.799
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              28988
_shelx_hkl_checksum              42893
_olex2_submission_special_instructions 'No special instructions were received'