A photo-induced three-component reaction of N-aryl piperidines, sulfur dioxide, and cycloketone oxime esters
Wang, Ze; Yu, Mengxia; Li, Shaoyu; Wu, Jie; Ye, Shengqing; Chemical Communications  (2026) –; doi:10.1039/D6CC01221C

data_7135751
_publ_section_title
;
 A photo-induced three-component reaction of <i>N</i>-aryl piperidines,
 sulfur dioxide, and cycloketone oxime esters.
;
_journal_issue                   37
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9429
_journal_page_last               9432
_journal_paper_doi               10.1039/d6cc01221c
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C18 H24 N2 O2 S'
_chemical_formula_sum            'C18 H24 N2 O2 S'
_chemical_formula_weight         332.45
_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
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2ntcb6
_audit_creation_date             2024-07-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-06-25 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.393(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.2169(15)
_cell_length_b                   10.9188(10)
_cell_length_c                   10.4535(10)
_cell_measurement_reflns_used    8839
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      27.980
_cell_measurement_theta_min      2.632
_cell_volume                     1766.4(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      301.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18569
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.336
_diffrn_reflns_theta_min         2.283
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6160
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1508 before and 0.0893 after correction.
The Ratio of minimum to maximum transmission is 0.8261.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         1.184
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0737
_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^)+(0.1169P)^2^+0.5095P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1925
_refine_ls_wR_factor_ref         0.2125
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3231
_reflns_number_total             4377
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc01221c2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7135751.cif.'
_cod_database_code               7135751
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C12(H12A,H12B), C11(H11A,H11B), C17(H17A,H17B), C16(H16A,
 H16B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C6(H6), C4(H4), C7(H7), C3(H3)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              34344
_olex2_submission_special_instructions 'No special instructions were received'