Phosphine-catalyzed [5+1] annulation of δ-sulfonamido-substituted enones with <i>N</i>-sulfonylimines: a facile synthesis of tetrahydropyridines.
Zhou, Leijie; Yuan, Chunhao; Zeng, Yuan; Liu, Honglei; Wang, Chang; Gao, Xing; Wang, Qijun; Zhang, Cheng; Guo, Hongchao; Chemical science 9 (2018) 1831–1835; doi:10.1039/c7sc04515h

data_1548702
_publ_section_title
;
 Phosphine-catalyzed [5+1] annulation of \d-sulfonamido-substituted enones
 with <i>N</i>-sulfonylimines: a facile synthesis of tetrahydropyridines.
;
_journal_issue                   7
_journal_name_full               'Chemical science'
_journal_page_first              1831
_journal_page_last               1835
_journal_paper_doi               10.1039/c7sc04515h
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H25 N O3 S'
_chemical_formula_sum            'C29 H25 N O3 S'
_chemical_formula_weight         467.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-20
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-09-18 deposited with the CCDC.
2018-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.345(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.769(3)
_cell_length_b                   13.123(3)
_cell_length_c                   10.039(3)
_cell_measurement_reflns_used    3431
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4775
_cell_measurement_theta_min      2.2267
_cell_volume                     1172.5(6)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
scan:
    Number of images: 270
               Slice: -110.0000 - 25.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 40.0758
              2theta: -20.3305
scan:
    Number of images: 300
               Slice: -110.0000 - 40.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 270.0000
                 XTD: 40.0758
              2theta: -20.3305
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0431
_diffrn_orient_matrix_UB_12      0.0194
_diffrn_orient_matrix_UB_13      -0.1019
_diffrn_orient_matrix_UB_21      -0.0302
_diffrn_orient_matrix_UB_22      -0.0653
_diffrn_orient_matrix_UB_23      -0.0252
_diffrn_orient_matrix_UB_31      -0.0658
_diffrn_orient_matrix_UB_32      0.0562
_diffrn_orient_matrix_UB_33      -0.0668
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.993
_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       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7830
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.899
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.406
_exptl_crystal_size_mid          0.315
_exptl_crystal_size_min          0.166
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1887 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4984
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0326P)^2^+0.3537P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0909
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    0.879
_reflns_Friedel_fraction_max     0.858
_reflns_number_gt                4802
_reflns_number_total             4984
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc04515h2.cif
_cod_data_source_block           sa4789a
_cod_depositor_comments          'Adding full bibliography for 1548702.cif.'
_cod_original_cell_volume        1172.6(5)
_cod_database_code               1548702
_diffrn_number_total             2789
_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:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C27(H27),
  C28(H28)
2.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C)
;
_shelx_res_checksum              3775
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'