Synthesis of substituted piperidines by enantioselective desymmetrizing intramolecular aza-Michael reactions.
Guerola, Marta; Escolano, Marcos; Alzuet-Piña, Gloria; Gómez-Bengoa, Enrique; Ramírez de Arellano, Carmen; Sánchez-Roselló, María; Del Pozo, Carlos; Organic & biomolecular chemistry 16 (2018) 4650–4658; doi:10.1039/c8ob01139g

data_7156281
_publ_section_title
;
 Synthesis of substituted piperidines by enantioselective desymmetrizing
 intramolecular aza-Michael reactions.
;
_journal_issue                   25
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4650
_journal_page_last               4658
_journal_paper_doi               10.1039/c8ob01139g
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C28 H44 Br N O4 S'
_chemical_formula_weight         570.61
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2018-03-13 deposited with the CCDC.
2018-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6897(3)
_cell_length_b                   11.2486(5)
_cell_length_c                   45.457(2)
_cell_measurement_reflns_used    4145
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.2840
_cell_measurement_theta_min      3.5810
_cell_volume                     2909.3(2)
_computing_cell_refinement       'CrysAlisPro (Agilent Tec., 2012)'
_computing_data_collection       'CrysAlisPro (Agilent Tec., 2012)'
_computing_data_reduction        'CrysAlisPro (Agilent Tec., 2012)'
_computing_molecular_graphics    'CrystalMaker 2.7 (1994-2013)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 16.0267
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'Agilent-XRD SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       64
_diffrn_reflns_limit_l_min       -61
_diffrn_reflns_number            18099
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         30.105
_diffrn_reflns_theta_min         3.586
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.517
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro (Agilent Tec., 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       lath
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
; 
 Flack x determined using 1828 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.024(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         7666
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0663
_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^)+(0.0245P)^2^+2.3935P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1170
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.852
_reflns_number_gt                6227
_reflns_number_total             7666
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01139g2.cif
_cod_data_source_block           psmg561
_cod_depositor_comments          'Adding full bibliography for 7156281.cif.'
_cod_database_code               7156281
_shelx_shelxl_version_number     2018/1
_shelx_res_checksum              94733