Diastereoselective synthesis of new zwitterionic bicyclic lactams, scaffolds for construction of 2-substituted-4-hydroxy piperidine and its pipecolic acid derivatives
Reyes-Bravo, Enrique; Gnecco, Dino; Juárez, Jorge R.; Orea, María L.; Bernès, Sylvain; Aparicio, David M.; Terán, Joel L.; RSC Advances 12 (2022) 4187–4190; doi:10.1039/D1RA09298G

data_7244329
_publ_section_title
;
 Diastereoselective synthesis of new zwitterionic bicyclic lactams,
 scaffolds for construction of 2-substituted-4-hydroxy piperidine and its
 pipecolic acid derivatives
;
_journal_issue                   7
_journal_name_full               'RSC Advances'
_journal_page_first              4187
_journal_page_last               4190
_journal_paper_doi               10.1039/D1RA09298G
_journal_volume                  12
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H17 N O3 S'
_chemical_formula_sum            'C15 H17 N O3 S'
_chemical_formula_weight         291.35
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-04-18
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2021-11-30 deposited with the CCDC.	2022-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                99.389(7)
_cell_angle_beta                 90.433(6)
_cell_angle_gamma                89.796(7)
_cell_formula_units_Z            2
_cell_length_a                   6.0976(4)
_cell_length_b                   9.5728(8)
_cell_length_c                   12.3463(10)
_cell_measurement_reflns_used    10706
_cell_measurement_temperature    243(1)
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.64
_cell_volume                     710.99(10)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2015)'
_computing_data_reduction        X-AREA
_computing_molecular_graphics
'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PublCif (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015a)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      243(1)
_diffrn_detector                 'Reverse-biased silicon diode array'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'Dectris Pilatus 100K R'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
1375 frames, 115 s/frame, 1 deg./frame, detector distance = 40 mm
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  -90
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_av_unetI/netI     0.1109
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17365
_diffrn_reflns_point_group_measured_fraction_full 0.890
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        19.664
_diffrn_reflns_theta_max         19.999
_diffrn_reflns_theta_min         2.636
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_current           0.600
_diffrn_source_power             0.039
_diffrn_source_type              'Axo Astix-f Microfocus source'
_diffrn_source_voltage           65
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       prism
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 782 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.20(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.901
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     375
_refine_ls_number_reflns         4804
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.900
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0532
_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^)+(0.0511P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1234
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_full    0.783
_reflns_Friedel_fraction_max     0.785
_reflns_number_gt                2713
_reflns_number_total             4804
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra09298g2.cif
_cod_data_source_block           22ab
_cod_database_code               7244329
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.951
_shelx_estimated_absorpt_t_max   0.994
_shelx_res_checksum              83697