Asymmetric β,γ'-regioselective [4 + 3] and [4 + 2] annulations of α-vinylenals <i>via</i> cascade iminium ion-dienamine catalysis.
Gao, Yang; Song, Xue; Yan, Ru-Jie; Du, Wei; Chen, Ying-Chun; Organic & biomolecular chemistry 19 (2021) 151–155; doi:10.1039/d0ob02068k

data_7157839
_publ_section_title
;
 Asymmetric \b,\g'-regioselective [4 + 3] and [4 + 2] annulations of
 \a-vinylenals <i>via</i> cascade iminium ion-dienamine catalysis.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              151
_journal_page_last               155
_journal_paper_doi               10.1039/d0ob02068k
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H20 N2 O2 S'
_chemical_formula_sum            'C24 H20 N2 O2 S'
_chemical_formula_weight         400.48
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-09-16
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2020-10-10 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.193(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1897(3)
_cell_length_b                   12.2546(5)
_cell_length_c                   10.5538(4)
_cell_measurement_reflns_used    4400
_cell_measurement_temperature    295.1(4)
_cell_measurement_theta_max      71.0680
_cell_measurement_theta_min      4.1960
_cell_volume                     1059.19(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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_environment      air
_diffrn_ambient_temperature      295.1(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -53.00  33.00   1.00    1.00    --  -34.98  57.00-180.00   86
  2  \w    -73.00  37.00   1.00    1.00    --  -34.98  19.00  90.00  110
  3  \w     16.00 103.00   1.00    1.00    --   34.98  57.00 -60.00   87
  4  \w     23.00  90.00   1.00    1.00    --   34.98-125.00 -30.00   67
  5  \w    -36.00  57.00   1.00    1.00    --   34.98 -38.00  60.00   93
  6  \w     87.00 175.00   1.00    1.53    --  106.90  61.00-150.00   88
  7  \w    100.00 178.00   1.00    1.53    --  106.90 111.00  60.00   78
  8  \w     39.00 127.00   1.00    1.53    --  106.90 -61.00 -60.00   88
  9  \w     35.00 133.00   1.00    1.53    --  106.90 -30.00  30.00   98
 10  \w    100.00 178.00   1.00    1.53    --  106.90 111.00 -30.00   78
 11  \w     36.00 111.00   1.00    1.53    --  106.90-104.00 -32.00   75
 12  \w    100.00 178.00   1.00    1.53    --  106.90 111.00 -90.00   78
 13  \w     39.00 127.00   1.00    1.53    --  106.90 -61.00 120.00   88
 14  \w     16.00  85.00   1.00    1.00    --   34.98  57.00-180.00   69
 15  \w     16.00 103.00   1.00    1.00    --   34.98  57.00  90.00   87
 16  \w    -44.00 -18.00   1.00    1.00    --  -35.35 -57.00 150.00   26
 17  \w   -100.00 -74.00   1.00    1.00    --  -35.35 -57.00 150.00   26
 18  \w     38.00  70.00   1.00    1.00    --   35.35-125.00  60.00   32
 19  \w     54.00  80.00   1.00    1.00    --   35.35-125.00-180.00   26
 20  \w     86.00 120.00   1.00    1.53    --  106.90  30.00  30.00   34
 21  \w    124.00 161.00   1.00    1.53    --  106.90  30.00  30.00   37
 22  \w     48.00 108.00   1.00    1.53    --  106.90-111.00 120.00   60
 23  \w     72.00 109.00   1.00    1.53    --  106.90 -94.00-180.00   37
 24  \w    110.00 175.00   1.00    1.53    --  106.90  45.00 120.00   65
 25  \w     78.00 103.00   1.00    1.53    --  106.90 -94.00   0.00   25
 26  \w     92.00 123.00   1.00    1.53    --  106.90  61.00  90.00   31
 27  \w     35.00  84.00   1.00    1.53    --  106.90 -30.00-180.00   49
 28  \w     49.00  83.00   1.00    1.53    --  106.90 -94.00 -90.00   34
 29  \w    148.00 177.00   1.00    1.53    --  106.90  45.00 150.00   29
 30  \w    -73.00  37.00   1.00    1.00    --  -35.35  19.00 -30.00  110
 31  \w      7.00 105.00   1.00    1.00    --   35.35  77.00-150.00   98
 32  \w      7.00 105.00   1.00    1.00    --   35.35  77.00  60.00   98
 33  \w      7.00 105.00   1.00    1.00    --   35.35  77.00 -60.00   98
 34  \w      7.00 105.00   1.00    1.00    --   35.35  77.00 120.00   98
 35  \w     23.00  90.00   1.00    1.00    --   35.35-125.00  90.00   67
 36  \w     17.00 104.00   1.00    1.00    --   35.35  57.00  30.00   87
 37  \w     23.00  90.00   1.00    1.00    --   35.35-125.00-150.00   67
 38  \w     81.00 171.00   1.00    1.53    --  106.90  30.00 -60.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1716143000
_diffrn_orient_matrix_UB_12      0.0392569000
_diffrn_orient_matrix_UB_13      0.0393097000
_diffrn_orient_matrix_UB_21      0.0547349000
_diffrn_orient_matrix_UB_22      -0.0042554000
_diffrn_orient_matrix_UB_23      -0.1394182000
_diffrn_orient_matrix_UB_31      -0.0543116000
_diffrn_orient_matrix_UB_32      0.1193462000
_diffrn_orient_matrix_UB_33      -0.0178889000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11399
_diffrn_reflns_point_group_measured_fraction_full 0.842
_diffrn_reflns_point_group_measured_fraction_max 0.826
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.462
_diffrn_reflns_theta_min         4.189
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.528
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       needle
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
;
 Flack x determined using 1088 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3390
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0930P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1319
_reflns_Friedel_coverage         0.594
_reflns_Friedel_fraction_full    0.669
_reflns_Friedel_fraction_max     0.648
_reflns_number_gt                3136
_reflns_number_total             3390
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02068k2.cif
_cod_data_source_block           5g
_cod_database_code               7157839
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C007(H007), C00B(H00C), C00D(H00E)
2.b Secondary CH2 refined with riding coordinates:
 C006(H00A,H00B), C00L(H00G,H00H)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00D), C00E(H00F), C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00T(H00T)
2.d Idealised Me refined as rotating group:
 C00S(H00I,H00L,H00R)
;
_shelx_res_checksum              2460
_shelx_hkl_checksum              6247
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2020-09-16
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.059
_oxdiff_exptl_absorpt_empirical_full_min 0.671