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_7244332
_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         'C7 H14 N O3, Cl, H2 O'
_chemical_formula_sum            'C7 H16 Cl N O4'
_chemical_formula_weight         213.66
_chemical_melting_point          369
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-10-14
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-11-30 deposited with the CCDC.	2022-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2312(5)
_cell_length_b                   9.1140(9)
_cell_length_c                   13.9693(10)
_cell_measurement_reflns_used    17116
_cell_measurement_temperature    295(1)
_cell_measurement_theta_max      23.84
_cell_measurement_theta_min      2.11
_cell_volume                     1047.97(14)
_computing_cell_refinement       'X-AREA 1.88'
_computing_data_collection       'X-AREA 1.88 (Stoe & Cie, 2019)'
_computing_data_reduction        'X-AREA 1.88'
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295(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 0.989
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
1545 frames, 100-140 s/frame, 1 deg./frame, detector distance = 50 mm
;
_diffrn_measurement_device       'Eulerian four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support Mitegen
_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  0.0792
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29183
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        19.664
_diffrn_reflns_theta_max         20.990
_diffrn_reflns_theta_min         2.105
_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    0.185
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.2094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-AREA 1.88 (Stoe & Cie, 2019)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       Plate
_exptl_crystal_F_000             456
_exptl_crystal_recrystallization_method
;
Re-crystallisation from solvent: Methanol/AcOEt
;
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.103
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 625 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.877
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0271
_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^)+(0.0247P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0501
_refine_ls_wR_factor_ref         0.0531
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                1768
_reflns_number_total             2273
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra09298g2.cif
_cod_data_source_block           38
_cod_database_code               7244332
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.923
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_checksum              89466