A Bifunctional N-Heterocyclic Carbene as a Noncovalent Organocatalyst for Enantioselective Aza-Michael Addition Reactions
Guo, Fangfang; Chen, Jiean; Huang, Yong; ACS Catalysis 11 (2021) 6316–6324; doi:10.1021/acscatal.1c01908

data_4518697
_publ_section_title
;
 A Bifunctional N-Heterocyclic Carbene as a Noncovalent Organocatalyst for
 Enantioselective Aza-Michael Addition Reactions
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              6316
_journal_page_last               6324
_journal_paper_doi               10.1021/acscatal.1c01908
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H22 F3 N3 O4'
_chemical_formula_sum            'C20 H22 F3 N3 O4'
_chemical_formula_weight         425.40
_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             2020-04-13
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.04.02 svn.r1fbe7b6f for OlexSys, GUI svn.r6076)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.14307(19)
_cell_length_b                   11.5592(3)
_cell_length_c                   19.6135(4)
_cell_measurement_reflns_used    6683
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.2390
_cell_measurement_theta_min      4.4120
_cell_volume                     2072.88(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_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     23.00  97.00   1.00    1.00    --   40.98-125.00-150.00   74
  2  \w    -33.00  65.00   1.00    1.00    --   40.98 -37.00 -60.00   98
  3  \w     17.00 115.00   1.00    1.00    --   40.98  37.00 150.00   98
  4  \w     35.00 136.00   1.00    1.20    --  106.95 -61.00  90.00  101
  5  \w     24.00 109.00   1.00    1.20    --  106.95 -94.00 -30.00   85
  6  \w     94.00 178.00   1.00    1.20    --  106.95 125.00-150.00   84
  7  \w     25.00 160.00   1.00    1.20    --  106.95 -15.00-150.00  135
  8  \w     78.00 178.00   1.00    1.20    --  106.95  61.00  30.00  100
  9  \w   -117.00 -67.00   1.00    1.00    --  -40.98 -77.00 -30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0035725000
_diffrn_orient_matrix_UB_12      -0.0430370000
_diffrn_orient_matrix_UB_13      -0.0743012000
_diffrn_orient_matrix_UB_21      0.0962601000
_diffrn_orient_matrix_UB_22      0.1028206000
_diffrn_orient_matrix_UB_23      -0.0217134000
_diffrn_orient_matrix_UB_31      0.1382672000
_diffrn_orient_matrix_UB_32      -0.0731916000
_diffrn_orient_matrix_UB_33      0.0130350000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10152
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.684
_diffrn_reflns_theta_min         4.440
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.973
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1567 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4093
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0295
_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^)+(0.0357P)^2^+0.1364P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0723
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                3929
_reflns_number_total             4093
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c01908_si_003.cif
_cod_data_source_block           sz0413-2
_cod_depositor_comments
'Adding full bibliography for 4518697--4518698.cif.'
_cod_database_code               4518697
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.901
_shelx_estimated_absorpt_t_min   0.884
_reflns_odcompleteness_completeness 99.95
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              3392
_shelx_hkl_checksum              16864
_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 1.531
_oxdiff_exptl_absorpt_empirical_full_min 0.616