Transforming 2D azolium salts to 3D caged tertiary amines via stereoselective dearomative cascade annulation
Patra, Koushik; Deb, Samiran; Kumar Choutipalli, Venkata Surya; Mulani, Sana; Mallik, Sumitava; Subramanian, Venkatesan; Baidya, Mahiuddin; Chemical Science 16 (2025) 7551–7559; doi:10.1039/D5SC01527H

data_1574241
_publ_section_title
;
 Transforming 2D azolium salts to 3D caged tertiary amines via
 stereoselective dearomative cascade annulation
;
_journal_issue                   17
_journal_name_full               'Chemical Science'
_journal_page_first              7551
_journal_page_last               7559
_journal_paper_doi               10.1039/D5SC01527H
_journal_volume                  16
_journal_year                    2025
_chemical_formula_sum            'C28 H29 N3 O3'
_chemical_formula_weight         455.54
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-07-15 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_c                   9.5517(7)
_cell_measurement_reflns_used    7067
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      24.98
_cell_measurement_theta_min      2.81
_cell_volume                     2429.1(3)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3(Bruker, 2016)'
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_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker axs kappa apex3 PHOTON II Diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1442
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            70501
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.047
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_min         2.716
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker 2016'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.032
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_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         4292
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0743
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0622P)^2^+1.6141P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1548
_refine_ls_wR_factor_ref         0.1627
_reflns_Friedel_coverage         0.876
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3593
_reflns_number_total             4292
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01527h3.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 1574241.cif.'
_cod_database_code               1574241
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.990
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              64497