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_7062720
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-11-25 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                   5.7785(3)
_cell_length_b                   7.4826(3)
_cell_length_c                   27.8645(11)
_cell_measurement_reflns_used    1587
_cell_measurement_temperature    240.00(10)
_cell_measurement_theta_max      71.5080
_cell_measurement_theta_min      6.1270
_cell_volume                     1204.81(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_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      N~2~
_diffrn_ambient_temperature      240.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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   -109.00 -60.00   1.00    1.50    --  -40.70 -57.00 -90.00   49
  2  \w    -66.00 -22.00   1.00    1.50    --  -40.70 125.00-150.00   44
  3  \w    -53.00  18.00   1.00    1.50    --  -40.70  38.00-150.00   71
  4  \w     78.00 176.00   1.00    1.50    --  104.23  30.00   0.00   98
  5  \w     58.00 112.00   1.00    1.50    --  104.23-125.00 -90.00   54
  6  \w     31.00  97.00   1.00    1.50    --  104.23 -30.00-180.00   66
  7  \w     35.00 128.00   1.00    1.50    --  104.23 -61.00  90.00   93
;
_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      0.0098393000
_diffrn_orient_matrix_UB_12      -0.0944341000
_diffrn_orient_matrix_UB_13      -0.0490722000
_diffrn_orient_matrix_UB_21      -0.0124733000
_diffrn_orient_matrix_UB_22      -0.1829033000
_diffrn_orient_matrix_UB_23      0.0252868000
_diffrn_orient_matrix_UB_31      -0.2660993000
_diffrn_orient_matrix_UB_32      0.0050531000
_diffrn_orient_matrix_UB_33      -0.0030385000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3366
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.514
_diffrn_reflns_theta_max         66.514
_diffrn_reflns_theta_min         6.124
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.793
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 674 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.029(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0377P)^2^+0.1066P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0840
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                1884
_reflns_number_total             2090
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj02537c2.cif
_cod_data_source_block           1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7062719--7062720.cif.'
_cod_database_code               7062720
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.749
_shelx_estimated_absorpt_t_min   0.713
_diffrn_oxdiff_digest_frames
;
01355152ea0cfbc9216873b40b940162a7004979b94
;
_diffrn_oxdiff_digest_hkl
;
01f0afa80d5a7661176d3b2352e837d26975bb
;
_reflns_odcompleteness_completeness 99.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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:
 C7(H7), 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              12127
_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 1.710
_oxdiff_exptl_absorpt_empirical_full_min 0.626