Selective synthesis of gem-dihalopiperidines and 4-halo-1,2,3,6-tetrahydropyridines from halogen substituted homoallylic benzenesulfonamides and aldehydes
Bora, Surjya Kumar; Saikia, Anil K.; RSC Advances 15 (2025) 21257–21268; doi:10.1039/D5RA03630E

data_7250580
_publ_section_title
;
 Selective synthesis of gem-dihalopiperidines and
 4-halo-1,2,3,6-tetrahydropyridines from halogen substituted homoallylic
 benzenesulfonamides and aldehydes
;
_journal_issue                   27
_journal_name_full               'RSC Advances'
_journal_page_first              21257
_journal_page_last               21268
_journal_paper_doi               10.1039/D5RA03630E
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C18 H18 Br N O2 S'
_chemical_formula_sum            'C18 H18 Br N O2 S'
_chemical_formula_weight         392.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2025-03-05 deposited with the CCDC.	2025-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.635(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.378(2)
_cell_length_b                   8.0513(15)
_cell_length_c                   19.674(4)
_cell_measurement_reflns_used    9562
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.32
_cell_measurement_theta_min      2.42
_cell_volume                     1726.9(6)
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            39994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         1.868
_exptl_absorpt_coefficient_mu    2.510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.3992
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.811
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0493
_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^)+(0.0529P)^2^+1.7176P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1373
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2546
_reflns_number_total             3955
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra03630e3.cif
_cod_data_source_block           SKB_OL_0ma_a
_cod_original_cell_volume        1726.9(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7250580
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.720
_shelx_estimated_absorpt_t_max   0.824
_shelx_res_checksum              12317