Heteropolyacid-Containing Ionic Liquid-Catalyzed Multicomponent Synthesis of Bridgehead Nitrogen Heterocycles: Mechanisms and Mitochondrial Staining.
Alvim, Haline G. O.; Correa, Jose R.; Assumpção, José A F; da Silva, Wender A.; Rodrigues, Marcelo O.; de Macedo, Julio L.; Fioramonte, Mariana; Gozzo, Fabio C.; Gatto, Claudia C.; Neto, Brenno A. D.; The Journal of organic chemistry 83 (2018) 4044–4053; doi:10.1021/acs.joc.8b00472

data_4035461
_publ_section_title
;
 Heteropolyacid-Containing Ionic Liquid-Catalyzed Multicomponent Synthesis
 of Bridgehead Nitrogen Heterocycles: Mechanisms and Mitochondrial
 Staining.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4044
_journal_page_last               4053
_journal_paper_doi               10.1021/acs.joc.8b00472
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C25 H24 N2'
_chemical_formula_sum            'C25 H24 N2'
_chemical_formula_weight         352.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2018-02-07 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 110.13(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.985(6)
_cell_length_b                   19.848(9)
_cell_length_c                   10.700(6)
_cell_measurement_reflns_used    578
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      12.7455
_cell_measurement_theta_min      2.2707
_cell_volume                     1991.0(19)
_computing_cell_refinement       'Bruker SAINT V8.18C (Bruker AXS Inc.)'
_computing_data_collection       'Bruker Instrument Service v2011.2.0.0'
_computing_data_reduction        'Bruker SAINT V8.18C (Bruker AXS Inc.)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2021
_diffrn_reflns_av_unetI/netI     0.3532
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11298
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.052
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.503
_exptl_crystal_size_mid          0.473
_exptl_crystal_size_min          0.267
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.892
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.892
_refine_ls_R_factor_all          0.3585
_refine_ls_R_factor_gt           0.0765
_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^)+(0.0621P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.2188
_reflns_Friedel_coverage         0.000
_reflns_number_gt                787
_reflns_number_total             3447
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {d3bc6e03-71b1-4b9b-b3e9-32a20a2156d2}
_cod_data_source_file            jo8b00472_si_002.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        1991.0(18)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4035461
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.982
_shelx_res_checksum              1259
_shelx_hkl_checksum              87472