Biocompatible synthesis of macrocyclic thiazole peptides from chiral α-amino nitriles.
Shang, Minghao; He, Junming; Gardiner, Michael G.; Nitsche, Christoph; Organic & biomolecular chemistry 23 (2025) 9815–9818; doi:10.1039/d4ob01989j

data_7160314
_publ_section_title
;
 Biocompatible synthesis of macrocyclic thiazole peptides from chiral
 &#x3b1;-amino nitriles.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9815
_journal_page_last               9818
_journal_paper_doi               10.1039/d4ob01989j
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C11 H20 N2 O2'
_chemical_formula_sum            'C11 H20 N2 O2'
_chemical_formula_weight         212.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-08-07
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-12-03 deposited with the CCDC.	2024-12-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.138(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.12630(10)
_cell_length_b                   10.4781(3)
_cell_length_c                   12.0133(3)
_cell_measurement_reflns_used    5065
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      77.7060
_cell_measurement_theta_min      5.6020
_cell_volume                     638.78(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.979
_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   -112.00 -71.00   0.50    1.00    --  -46.45-129.00  51.00   82
  2  \w   -113.00 -62.00   0.50    1.00    --  -46.45-141.00-121.00  102
  3  \w    -87.00 -62.00   0.50    1.00    --  -46.45 141.00 -63.00   50
  4  \w    -76.00 -51.00   0.50    1.00    --  -46.45 129.00 124.00   50
  5  \w     45.00  91.00   0.50    1.00    --   46.45-129.00  51.00   92
  6  \w     43.00  99.00   0.50    1.00    --   46.45-141.00-121.00  112
  7  \w     85.00 115.00   0.50    2.00    --  107.75 141.00 -63.00   60
  8  \w     72.00 110.00   0.50    2.00    --  107.75-129.00  51.00   76
  9  \w    105.00 135.00   0.50    2.00    --  107.75 129.00 124.00   60
 10  \w     78.00 118.00   0.50    2.00    --  107.75-141.00-121.00   80
 11  \w     -5.00  28.00   0.50    1.00    --  -46.45  19.00 -90.00   66
 12  \w     -8.00  30.00   0.50    1.00    --  -46.45  19.00 120.00   76
 13  \w      1.00  27.00   0.50    1.00    --  -46.45  19.00 -30.00   52
 14  \w     -8.00  17.00   0.50    1.00    --  -46.45  19.00 150.00   50
 15  \w     -1.00  30.00   0.50    1.00    --  -46.45  19.00 -60.00   62
 16  \w    -18.00  14.00   0.50    1.00    --  -46.45  38.00  60.00   64
 17  \w     -2.00  23.00   0.50    1.00    --  -46.45  19.00-180.00   50
 18  \w     -5.00  21.00   0.50    1.00    --  -46.45  19.00  30.00   52
 19  \w     -8.00  17.00   0.50    1.00    --  -46.45  19.00-150.00   50
 20  \w     32.00  57.00   0.50    2.00    --  107.75 -30.00 -90.00   50
 21  \w     84.00 110.00   0.50    2.00    --  107.75-125.00   0.00   52
 22  \w     38.00  79.00   0.50    2.00    --  107.75-125.00   0.00   82
 23  \w     38.00  80.00   0.50    2.00    --  107.75-125.00 -30.00   84
 24  \w     32.00  58.00   0.50    2.00    --  107.75 -30.00 120.00   52
 25  \w     32.00  57.00   0.50    2.00    --  107.75 -30.00 150.00   50
 26  \w     32.00  57.00   0.50    2.00    --  107.75 -30.00-150.00   50
 27  \w     94.00 136.00   0.50    2.00    --  107.75  30.00-120.00   84
 28  \w    136.00 166.00   0.50    2.00    --  107.75  15.00 150.00   60
 29  \w     94.00 133.00   0.50    2.00    --  107.75  15.00 150.00   78
 30  \w     40.00  73.00   0.50    2.00    --  107.75 -45.00  90.00   66
 31  \w     32.00  57.00   0.50    2.00    --  107.75 -30.00  60.00   50
 32  \w    153.00 178.00   0.50    2.00    --  107.75 125.00 150.00   50
 33  \w    144.00 173.00   0.50    2.00    --  107.75  30.00-120.00   58
 34  \w     37.00  70.00   0.50    2.00    --  107.75 -95.00-150.00   66
 35  \w     76.00 103.00   0.50    2.00    --  107.75 -95.00-150.00   54
 36  \w     35.00  60.00   0.50    2.00    --  107.75 -45.00 -60.00   50
 37  \w    105.00 148.00   0.50    2.00    --  107.75 125.00 150.00   86
 38  \w     46.00  71.00   0.50    2.00    --  107.75 -45.00  30.00   50
 39  \w     87.00 112.00   0.50    2.00    --  107.75-125.00 -30.00   50
 40  \w     37.00  87.00   0.50    2.00    --  107.75 -95.00  60.00  100
 41  \w     55.00 104.00   0.50    2.00    --  107.75 -95.00-120.00   98
 42  \w     40.00 100.00   0.50    2.00    --  107.75 -95.00 150.00  120
 43  \w     41.00 110.00   0.50    2.00    --  107.75-125.00 150.00  138
 44  \w     42.00  86.00   0.50    2.00    --  107.75 -61.00-150.00   88
 45  \w     32.00  57.00   0.50    2.00    --  107.75 -30.00-120.00   50
 46  \w     41.00  89.00   0.50    2.00    --  107.75-125.00  30.00   96
 47  \w    103.00 129.00   0.50    2.00    --  107.75 125.00  60.00   52
 48  \w    150.00 175.00   0.50    2.00    --  107.75 125.00  60.00   50
 49  \w     95.00 101.00   0.50    2.00    --  107.75  45.00-150.00   12
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.3032652000
_diffrn_orient_matrix_UB_12      0.0057016000
_diffrn_orient_matrix_UB_13      0.0223746000
_diffrn_orient_matrix_UB_21      -0.0119298000
_diffrn_orient_matrix_UB_22      0.1467252000
_diffrn_orient_matrix_UB_23      0.0046321000
_diffrn_orient_matrix_UB_31      -0.0091350000
_diffrn_orient_matrix_UB_32      -0.0063351000
_diffrn_orient_matrix_UB_33      0.1275329000
_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  0.0356
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6805
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.907
_diffrn_reflns_theta_min         3.717
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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    1.104
_exptl_crystal_description       prism
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.207
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1036 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2578
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0936P)^2^+0.0107P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1284
_reflns_Friedel_coverage         0.818
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.897
_reflns_number_gt                2421
_reflns_number_total             2578
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01989j2.cif
_cod_data_source_block           ms-boc-ile-cnascaled010filtnon
_cod_depositor_comments          'Adding full bibliography for 7160314.cif.'
_cod_database_code               7160314
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C11H20N2O2
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.884
_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:
 C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C6(H6A,H6B,H6C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              33216
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MiTeGen holder in oil'
_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 1.562
_oxdiff_exptl_absorpt_empirical_full_min 0.643