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_7157838
_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         'C22 H18 Br F3 N2 O2'
_chemical_formula_sum            'C22 H18 Br F3 N2 O2'
_chemical_formula_weight         479.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-09-02
_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
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2936(3)
_cell_length_b                   14.1248(7)
_cell_length_c                   23.2960(9)
_cell_measurement_reflns_used    3427
_cell_measurement_temperature    293.9(3)
_cell_measurement_theta_max      70.7150
_cell_measurement_theta_min      3.6230
_cell_volume                     2070.92(16)
_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      293.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.971
_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 -30.00   86
  2  \w      1.00  75.00   1.00    1.00    --   34.98 -99.00 150.00   74
  3  \w      1.00  75.00   1.00    1.00    --   34.98 -99.00-120.00   74
  4  \w      1.00  75.00   1.00    1.00    --   34.98 -99.00-150.00   74
  5  \w    -36.00  57.00   1.00    1.00    --   34.98 -38.00-120.00   93
  6  \w      1.00  75.00   1.00    1.00    --   34.98 -99.00 -60.00   74
  7  \w     37.00 127.00   1.00    2.13    --  106.90 -45.00 120.00   90
  8  \w     37.00 110.00   1.00    2.13    --  106.90 -94.00  90.00   73
  9  \w    100.00 178.00   1.00    2.13    --  106.90 111.00  90.00   78
 10  \w     39.00 127.00   1.00    2.13    --  106.90 -61.00-120.00   88
 11  \w     37.00 110.00   1.00    2.13    --  106.90 -94.00-180.00   73
 12  \w    100.00 178.00   1.00    2.13    --  106.90 111.00 -30.00   78
 13  \w     39.00 127.00   1.00    2.13    --  106.90 -61.00  60.00   88
;
_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      0.0003775000
_diffrn_orient_matrix_UB_12      0.0954418000
_diffrn_orient_matrix_UB_13      -0.0319875000
_diffrn_orient_matrix_UB_21      -0.0735045000
_diffrn_orient_matrix_UB_22      -0.0503755000
_diffrn_orient_matrix_UB_23      -0.0552330000
_diffrn_orient_matrix_UB_31      -0.2333834000
_diffrn_orient_matrix_UB_32      0.0159607000
_diffrn_orient_matrix_UB_33      0.0173396000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9369
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.371
_diffrn_reflns_theta_min         3.660
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.136
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67109
_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    1.537
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details
;
 Flack x determined using 1309 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3888
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0634
_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^)+(0.1153P)^2^+0.2819P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1675
_refine_ls_wR_factor_ref         0.1749
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                3548
_reflns_number_total             3888
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02068k2.cif
_cod_data_source_block           3b
_cod_original_cell_volume        2070.91(17)
_cod_database_code               7157838
_reflns_odcompleteness_completeness 98.45
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00E(H00E), C00H(H00H)
2.b Secondary CH2 refined with riding coordinates:
 C00N(H00A,H00C)
2.c Aromatic/amide H refined with riding coordinates:
 N004(H004), C00B(H00B), C00D(H00D), C00J(H00J), C00L(H00L), C00O(H00O),
 C00P(H00P), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U)
2.d Idealised Me refined as rotating group:
 C00Q(H00F,H00G,H00I)
;
_shelx_res_checksum              4111
_shelx_hkl_checksum              36095
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2020-09-02
_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 1.422
_oxdiff_exptl_absorpt_empirical_full_min 0.718