Asymmetric iminium ion-catalyzed conjugate addition of 2-hydroxycinnamaldehydes and 2-oxocarboxylic esters: synthesis of chiral polysubstituted bridged bicyclic ketals.
Ming, Yong-Chao; Lv, Xue-Jiao; Chen, Ying-Han; Liu, Yan-Kai; Chemical communications (Cambridge, England)  (2023) –; doi:10.1039/d3cc02739b

data_7131779
_publ_section_title
;
 Asymmetric iminium ion-catalyzed conjugate addition of
 2-hydroxycinnamaldehydes and 2-oxocarboxylic esters: synthesis of chiral
 polysubstituted bridged bicyclic ketals.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d3cc02739b
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H15 Cl O4'
_chemical_formula_sum            'C15 H15 Cl O4'
_chemical_formula_weight         294.72
_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     dual
_audit_creation_date             2022-06-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-10-01 deposited with the CCDC.	2023-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0599(8)
_cell_length_b                   13.909(2)
_cell_length_c                   17.1498(18)
_cell_measurement_reflns_used    1098
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3680
_cell_measurement_theta_min      5.1460
_cell_volume                     1445.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1281
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.962
_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    -13.00  23.00   1.00    1.00    --    0.00 -77.00 -30.00   36
  2  \w    -18.00  10.00   1.00    1.00    --    0.00 -77.00 -90.00   28
  3  \w      1.00  30.00   1.00    1.00    --    0.00 -77.00  30.00   29
  4  \w     66.00 109.00   1.00    1.00    --   54.63  57.00-180.00   43
  5  \w    -16.00  69.00   1.00    1.00    --   54.63 -37.00   0.00   85
  6  \w    -13.00  43.00   1.00    1.00    --   54.63 -57.00-120.00   56
  7  \w    104.00 152.00   1.00    1.00    --  109.26 111.00 -30.00   48
  8  \w    138.00 171.00   1.00    1.00    --  109.26  25.00 150.00   33
  9  \w     54.00  97.00   1.00    1.00    --  109.26 -91.00-150.00   43
 10  \w    102.00 173.00   1.00    1.00    --  109.26  77.00-120.00   71
 11  \w     92.00 134.00   1.00    1.00    --  109.26  25.00 150.00   42
 12  \w    132.00 175.00   1.00    1.00    --  109.26 111.00 -60.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2485611000
_diffrn_orient_matrix_UB_12      0.0145738000
_diffrn_orient_matrix_UB_13      -0.0148716000
_diffrn_orient_matrix_UB_21      -0.0008232000
_diffrn_orient_matrix_UB_22      -0.0877488000
_diffrn_orient_matrix_UB_23      -0.0548262000
_diffrn_orient_matrix_UB_31      -0.0534261000
_diffrn_orient_matrix_UB_32      -0.0658211000
_diffrn_orient_matrix_UB_33      0.0696374000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3200
_diffrn_reflns_point_group_measured_fraction_full 0.821
_diffrn_reflns_point_group_measured_fraction_max 0.798
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.940
_diffrn_reflns_theta_min         4.092
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.439
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 258 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(2)
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.0656
_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^)+(0.0798P)^2^+1.3311P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1605
_refine_ls_wR_factor_ref         0.2282
_reflns_Friedel_coverage         0.414
_reflns_Friedel_fraction_full    0.594
_reflns_Friedel_fraction_max     0.565
_reflns_number_gt                1138
_reflns_number_total             2226
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02739b3.cif
_cod_data_source_block           exp_12776_auto
_cod_database_code               7131779
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.793
_shelx_estimated_absorpt_t_min   0.641
_reflns_odcompleteness_completeness 98.24
_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:
 C004(H004), C009(H009)
2.b Secondary CH2 refined with riding coordinates:
 C00J(H00G,H00I)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H)
2.d Idealised Me refined as rotating group:
 C00A(H00A,H00B,H00C), C00K(H00J,H00K,H00L)
;
_shelx_res_checksum              49592
_shelx_hkl_checksum              42559
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.372
_oxdiff_exptl_absorpt_empirical_full_min 0.808