[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_7157550
_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_absolute_configuration ad
_chemical_formula_sum            'C16 H17 N'
_chemical_formula_weight         223.30
_chemical_name_common            5
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.2231(2)
_cell_length_b                   14.5123(4)
_cell_length_c                   22.3944(6)
_cell_measurement_reflns_used    9741
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.00
_cell_measurement_theta_min      3.63
_cell_volume                     2347.47(11)
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            58893
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.310
_diffrn_reflns_theta_min         3.629
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.553
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.5855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.567
_exptl_crystal_size_mid          0.255
_exptl_crystal_size_min          0.199
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
; 
 Flack x determined using 2037 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 Absolute structure confirmed using Bayesian statistics [P3 
 (rac-twin) 0.1E-04] (Hooft, Straver, and Spek, J. Appl. Cryst. 
 (2008), 41, 96-103). 
;
_refine_ls_abs_structure_Flack   -0.12(14)
_refine_ls_extinction_coef       0.0019(3)
_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   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0318
_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^)+(0.0457P)^2^+0.5375P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0818
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4827
_reflns_number_total             4974
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01156h2.cif
_cod_data_source_block           D19144
_cod_depositor_comments
'Adding full bibliography for 7157550--7157551.cif.'
_cod_database_code               7157550
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.745
_shelx_estimated_absorpt_t_max   0.898
_shelx_res_checksum              92093