[1,2]-Rearrangement of iminium salts provides access to heterocycles with adamantane scaffold.
Zonker, Benjamin; Duman, Ediz; Hausmann, Heike; Becker, Jonathan; Hrdina, Radim; Organic & biomolecular chemistry 18 (2020) 4941–4945; doi:10.1039/d0ob01156h

data_7157551
_publ_section_title
;
 [1,2]-Rearrangement of iminium salts provides access to heterocycles with
 adamantane scaffold.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4941
_journal_page_last               4945
_journal_paper_doi               10.1039/d0ob01156h
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C20 H26 N O'
_chemical_formula_weight         296.42
_chemical_name_common            8
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-04-30 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.1403(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.1498(9)
_cell_length_b                   10.3031(3)
_cell_length_c                   11.3085(4)
_cell_measurement_reflns_used    9031
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.02
_cell_measurement_theta_min      2.77
_cell_volume                     3162.67(18)
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker PHOTON100'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            63246
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.505
_diffrn_reflns_theta_min         2.114
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1288
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.331
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.0024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         5274
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0460
_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^)+(0.0701P)^2^+1.9108P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1303
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4204
_reflns_number_total             5274
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01156h2.cif
_cod_data_source_block           D19274
_cod_depositor_comments
'Adding full bibliography for 7157550--7157551.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7157551
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.975
_shelx_estimated_absorpt_t_max   0.996
_shelx_res_checksum              9639