Suppression of rapid deactivation of catalytic tetrapeptides in the asymmetric Michael addition of aldehydes to nitroolefins by supporting them on polymers.
Yuan, Meng; Liu, Yang-Xin; Ding, Tie-Ying; Zhang, Ze-Xuan; Lian, Tian-Rui; Zhao, Peng-Fei; Du, Zhi-Hong; Da, Chao-Shan; Organic & biomolecular chemistry 23 (2025) 6819–6831; doi:10.1039/d5ob00667h

data_7160605
_publ_section_title
;
 Suppression of rapid deactivation of catalytic tetrapeptides in the
 asymmetric Michael addition of aldehydes to nitroolefins by supporting
 them on polymers.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6819
_journal_page_last               6831
_journal_paper_doi               10.1039/d5ob00667h
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H43 N5 O4, H2 O'
_chemical_formula_sum            'C23 H45 N5 O5'
_chemical_formula_weight         471.64
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-01-24 deposited with the CCDC.	2025-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3017(2)
_cell_length_b                   10.6010(2)
_cell_length_c                   27.7102(6)
_cell_measurement_reflns_used    12176
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.3600
_cell_measurement_theta_min      3.1980
_cell_volume                     2732.43(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_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      4.00  77.00   0.50    0.05    --   46.68-105.00  43.00  146
  2  \w     37.00  67.00   0.50    0.05    --  104.76 -94.00 -90.00   60
  3  \w     79.00 105.00   0.50    0.05    --  104.76 -94.00 -90.00   52
  4  \w     38.00  87.00   0.50    0.05    --  104.76-105.00  43.00   98
  5  \w     35.00  94.00   0.50    0.05    --  104.76 -77.00 150.00  118
  6  \w    -28.00  -1.00   0.50    0.05    --   46.68 -19.00 150.00   54
  7  \w   -168.00 -89.00   0.50    0.05    -- -102.00 -45.00  90.00  158
  8  \w   -162.00 -89.00   0.50    0.05    -- -102.00 -33.00-110.00  146
  9  \w   -175.00-132.00   0.50    0.05    -- -102.00 -15.00 150.00   86
 10  \w   -113.00 -88.00   0.50    0.05    -- -102.00 -15.00 150.00   50
 11  \w    -66.00 -40.00   0.50    0.05    -- -102.00  61.00 150.00   52
 12  \w    -38.00  11.00   0.50    0.05    --  -46.68  37.00 150.00   98
 13  \w    -69.00 -31.00   0.50    0.05    -- -102.00  61.00  90.00   76
 14  \w    -60.00 -32.00   0.50    0.05    -- -102.00  61.00  30.00   56
 15  \w    -37.00  26.00   0.50    0.05    --  -46.68  37.00 -90.00  126
 16  \w   -103.00 -60.00   0.50    0.05    -- -102.00  97.00-116.00   86
 17  \w   -108.00 -32.00   0.50    0.05    -- -102.00 125.00 -60.00  152
 18  \w   -105.00 -64.00   0.50    0.05    -- -102.00 105.00 143.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0105122000
_diffrn_orient_matrix_UB_12      -0.0531768000
_diffrn_orient_matrix_UB_13      0.0516234000
_diffrn_orient_matrix_UB_21      0.1596668000
_diffrn_orient_matrix_UB_22      0.0317456000
_diffrn_orient_matrix_UB_23      0.0084317000
_diffrn_orient_matrix_UB_31      -0.0428744000
_diffrn_orient_matrix_UB_32      0.1314432000
_diffrn_orient_matrix_UB_33      0.0188292000
_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  0.0421
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16423
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.471
_diffrn_reflns_theta_min         3.190
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
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    1.146
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1964 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5422
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0579P)^2^+0.1442P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1008
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                5006
_reflns_number_total             5422
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00667h2.cif
_cod_data_source_block           yuanmeng-dchsh_0725_auto
_cod_depositor_comments
'Adding full bibliography for 7160604--7160605.cif.'
_cod_database_code               7160605
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 99.86
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O4(H4A,H4B)
2.b Ternary CH refined with riding coordinates:
 C2(H2), C12(H12), C14(H14), C16(H16)
2.c Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C13(H13A,H13B), C15(H15A,H15B), C18(H18A,H18B), C22(H22A,H22B)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C11(H11A,
 H11B,H11C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              84464
_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 1.970
_oxdiff_exptl_absorpt_empirical_full_min 0.549