Chiral cyclopropenimine-catalyzed enantioselective Michael additions between benzophenone-imine of glycine esters and α,β-unsaturated pyrazolamides
Bai, Yu-Jun; Wang, Xue-Ying; Zhu, Si-Kai; Zheng, Xiao-Hui; Zhang, Sheng-Yong; Wang, Ping-An; New Journal of Chemistry 47 (2023) 18811–18817; doi:10.1039/D3NJ02537C

data_7062719
_publ_section_title
;
 Chiral cyclopropenimine-catalyzed enantioselective Michael additions
 between benzophenone-imine of glycine esters and \a,\b-unsaturated
 pyrazolamides
;
_journal_issue                   40
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              18811
_journal_page_last               18817
_journal_paper_doi               10.1039/D3NJ02537C
_journal_volume                  47
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C12 H12 Cl N O3'
_chemical_formula_sum            'C12 H12 Cl N O3'
_chemical_formula_weight         253.68
_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
_audit_block_doi                 10.5517/ccdc.csd.cc29lrsg
_audit_creation_date             2021-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-08 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.78020(10)
_cell_length_b                   7.48790(10)
_cell_length_c                   27.7844(5)
_cell_measurement_reflns_used    3805
_cell_measurement_temperature    230.00(10)
_cell_measurement_theta_max      72.4380
_cell_measurement_theta_min      6.1130
_cell_volume                     1202.55(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      230.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -113.00 -51.00   1.00    1.00    --  -40.70 -58.00  40.00   62
  2  \w      1.00  28.00   1.00    1.00    --  -40.70  58.00-178.00   27
  3  \w    -68.00 -17.00   1.00    1.00    --  -40.70  58.00-178.00   51
  4  \w     91.00 117.00   1.00    1.00    --  104.23  58.00-178.00   26
  5  \w     31.00 133.00   1.00    1.00    --  104.23 -58.00  40.00  102
  6  \w    -87.00 -10.00   1.00    1.00    --  -40.70 125.00 -90.00   77
  7  \w     17.00  43.00   1.00    1.00    --   40.70 -58.00  40.00   26
  8  \w     79.00 173.00   1.00    1.00    --  104.23  45.00 120.00   94
  9  \w     31.00 130.00   1.00    1.00    --  104.23 -45.00-180.00   99
 10  \w     72.00 167.00   1.00    1.00    --  104.23  15.00 -60.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0397549000
_diffrn_orient_matrix_UB_12      0.1969852000
_diffrn_orient_matrix_UB_13      0.0137789000
_diffrn_orient_matrix_UB_21      -0.2037771000
_diffrn_orient_matrix_UB_22      0.0097639000
_diffrn_orient_matrix_UB_23      -0.0356363000
_diffrn_orient_matrix_UB_31      -0.1670313000
_diffrn_orient_matrix_UB_32      -0.0587460000
_diffrn_orient_matrix_UB_33      0.0401790000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            4506
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        65.931
_diffrn_reflns_theta_max         65.931
_diffrn_reflns_theta_min         6.121
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.798
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 785 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(6)
_refine_ls_extinction_coef       0.0138(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0251
_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^)+(0.0350P)^2^+0.1460P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0669
_reflns_Friedel_coverage         0.656
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2021
_reflns_number_total             2082
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj02537c2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7062719--7062720.cif.'
_cod_database_code               7062719
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.787
_shelx_estimated_absorpt_t_min   0.748
_diffrn_oxdiff_digest_frames
;
01156600571559a1b37859f990c3c777b100030f7e1
;
_diffrn_oxdiff_digest_hkl
;
014260d1841e06ed44ac084874ef41da982709
;
_reflns_odcompleteness_completeness 99.85
_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:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              44052
_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 1.331
_oxdiff_exptl_absorpt_empirical_full_min 0.802