Sulfonyl radical-induced regioselective cyclization of 3-aza-1,5-enynes with sulfonyl chlorides to produce 1,2-dihydropyridines by copper catalysis
Ding, Ran; Fu, Jian-Ming; Tian, Hai-Yu; Chen, Nian-Shou; Liu, Lei; Guo, Yu; Wang, Pei-Long; New Journal of Chemistry 45 (2021) 11030–11034; doi:10.1039/D1NJ01821C

data_7060693
_publ_section_title
;
 Sulfonyl radical-induced regioselective cyclization of 3-aza-1,5-enynes
 with sulfonyl chlorides to produce 1,2-dihydropyridines by copper
 catalysis
;
_journal_issue                   25
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11030
_journal_page_last               11034
_journal_paper_doi               10.1039/D1NJ01821C
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C28 H27 N O3 S'
_chemical_formula_sum            'C28 H27 N O3 S'
_chemical_formula_weight         457.56
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-15 deposited with the CCDC.	2021-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                117.285(3)
_cell_angle_beta                 92.754(4)
_cell_angle_gamma                90.642(4)
_cell_formula_units_Z            4
_cell_length_a                   9.9944(11)
_cell_length_b                   16.6828(18)
_cell_length_c                   16.8624(18)
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.674
_cell_measurement_theta_min      3.015
_cell_volume                     2494.1(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_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  0.0605
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            51807
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.564
_diffrn_reflns_theta_min         3.095
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0866 before and 0.0695 after correction.
The Ratio of minimum to maximum transmission is 0.9137.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     601
_refine_ls_number_reflns         11419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.0743
_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^)+(0.1236P)^2^+0.8232P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1941
_refine_ls_wR_factor_ref         0.2195
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7315
_reflns_number_total             11419
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj01821c2.cif
_cod_data_source_block           111
_cod_depositor_comments          'Adding full bibliography for 7060693.cif.'
_cod_database_code               7060693
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.961
_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 Secondary CH2 refined with riding coordinates:
 C40(H40A,H40B), C47(H47A,H47B), C19(H19A,H19B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C42(H42), C52(H52), C43(H43), C55(H55), C54(H54), C32(H32), C34(H34),
 C44(H44), C53(H53), C35(H35), C46(H46), C56(H56), C45(H45), C31(H31), C23(H23),
  C18(H18), C24(H24), C14(H14), C4(H4), C3(H3), C26(H26), C6(H6), C22(H22),
 C17(H17), C16(H16), C7(H7), C25(H25), C15(H15)
2.c Idealised Me refined as rotating group:
 C50(H50A,H50B,H50C), C48(H48A,H48B,H48C), C29(H29A,H29B,H29C), C28(H28A,H28B,
 H28C), C20(H20A,H20B,H20C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              39721
_olex2_submission_special_instructions 'No special instructions were received'