Synthesis of bridgehead-azacycles <i>via</i> dual C-N/C-C annulation of α-amino acids, aminals and maleimides.
Thadem, Nagender; Rajesh, Manda; Balaboina, Harikrishna; Das, Saibal; Organic & biomolecular chemistry  (2022) –; doi:10.1039/d2ob01117d

data_7158793
_publ_section_title
;
 Synthesis of bridgehead-azacycles <i>via</i> dual C-N/C-C annulation of
 \a-amino acids, aminals and maleimides.
;
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_paper_doi               10.1039/d2ob01117d
_journal_year                    2022
_chemical_formula_moiety         '2(C22 H18 F N3 O3), C H2 Cl2'
_chemical_formula_sum            'C45 H38 Cl2 F2 N6 O6'
_chemical_formula_weight         867.71
_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_Hall           'A 2 -2ab'
_space_group_name_H-M_alt        'A e a 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-02-24 deposited with the CCDC.	2022-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.524(2)
_cell_length_b                   24.034(7)
_cell_length_c                   7.426(6)
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      23.621
_cell_measurement_theta_min      2.4785
_cell_volume                     4020(3)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            32846
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.522
_diffrn_reflns_theta_min         2.479
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1642 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         6106
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0374P)^2^+2.0770P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0991
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4453
_reflns_number_total             6106
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01117d2.cif
_cod_data_source_block           KB312_1_0m
_cod_original_sg_symbol_Hall     'A 2 -2ac'
_cod_original_sg_symbol_H-M      'A b a 2'
_cod_database_code               7158793
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.940
_shelx_estimated_absorpt_t_max   0.964
_shelx_res_checksum              19261