A multicomponent approach for the stereoselective synthesis of atropisomeric N-N peptide analogues.
Roper, Natalie J.; Hardy, George M.; Wootton, Jack M.; Waddell, Paul G.; Wilson, James; Armstrong, Roly J.; Chemical communications (Cambridge, England) 61 (2025) 17388–17391; doi:10.1039/d5cc05091j

data_7135068
_publ_section_title
;
 A multicomponent approach for the stereoselective synthesis of
 atropisomeric N-N peptide analogues.
;
_journal_issue                   89
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              17388
_journal_page_last               17391
_journal_paper_doi               10.1039/d5cc05091j
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C29 H29 N3 O4'
_chemical_formula_sum            'C29 H29 N3 O4'
_chemical_formula_weight         483.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-04
_audit_creation_method
;
Olex2 1.5-ac5-023
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2025-07-28 deposited with the CCDC.	2025-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.2700(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.91440(10)
_cell_length_b                   11.01290(10)
_cell_length_c                   20.0815(2)
_cell_measurement_reflns_used    18391
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      76.6800
_cell_measurement_theta_min      4.0070
_cell_volume                     2613.75(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.126a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.126a 64-bit (release 11-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.126a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.961
_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  69.00   0.50    0.36    --   46.11 -82.00 117.00  184
  2  \w    -55.00  22.00   0.50    0.36    --  -47.61  82.00-120.00  154
  3  \w    -83.00 -34.00   0.50    1.43    --  -92.22  82.00-120.00   98
  4  \w   -156.00 -79.00   0.50    1.43    --  -92.22 -82.00 117.00  154
  5  \w     98.00 123.00   0.50    1.43    --   95.82  82.00-120.00   50
  6  \w     39.00 138.00   0.50    1.43    --  107.32 -82.00 117.00  198
  7  \w    131.00 159.00   0.50    1.43    --  107.32  82.00-120.00   56
  8  \w     93.00 127.00   0.50    1.43    --  107.32  82.00-120.00   68
  9  \w     78.00 103.00   0.50    0.36    --   46.11 125.00-180.00   50
 10  \w     44.00 119.00   0.50    0.36    --   46.11  57.00 -60.00  150
 11  \w   -122.00 -78.00   0.50    0.36    --  -47.61-125.00-150.00   88
 12  \w    -21.00  32.00   0.50    0.36    --  -47.61  19.00 150.00  106
 13  \w    -35.00 -10.00   0.50    1.43    --  -92.22  30.00  30.00   50
 14  \w    -35.00  -9.00   0.50    1.43    --  -92.22  30.00  90.00   52
 15  \w   -155.00 -84.00   0.50    1.43    --  -92.22 -95.00-120.00  142
 16  \w    -35.00 -10.00   0.50    1.43    --  -92.22  30.00-180.00   50
 17  \w    -35.00 -10.00   0.50    1.43    --  -92.22  30.00-120.00   50
 18  \w   -120.00 -73.00   0.50    1.43    --  -92.22 -45.00 -30.00   94
 19  \w    -35.00 -10.00   0.50    1.43    --  -92.22  30.00 -90.00   50
 20  \w   -172.00-128.00   0.50    1.43    --  -92.22 -45.00 -30.00   88
 21  \w   -171.00 -78.00   0.50    1.43    --  -92.22 -45.00  30.00  186
 22  \w   -101.00 -51.00   0.50    1.43    --  -92.22 125.00-120.00  100
 23  \w    140.00 166.00   0.50    1.43    --   95.82  77.00-180.00   52
 24  \w     23.00  48.00   0.50    1.43    --   95.82 -45.00 150.00   50
 25  \w     65.00 126.00   0.50    1.43    --   95.82  77.00-180.00  122
 26  \w     17.00  47.00   0.50    1.43    --   95.82 -45.00  60.00   60
 27  \w     43.00 104.00   0.50    1.43    --   95.82 -77.00  30.00  122
 28  \w     37.00  83.00   0.50    1.43    --   95.82 -82.00 117.00   92
 29  \w     86.00 130.00   0.50    1.43    --  107.32  61.00 -30.00   88
 30  \w     72.00 104.00   0.50    1.43    --  107.32 -95.00  30.00   64
 31  \w     41.00  67.00   0.50    1.43    --  107.32 -61.00-180.00   52
 32  \w     42.00  69.00   0.50    1.43    --  107.32 -61.00-120.00   54
 33  \w     32.00  69.00   0.50    1.43    --  107.32 -61.00 120.00   74
 34  \w     33.00  59.00   0.50    1.43    --  107.32 -61.00  30.00   52
 35  \w    153.00 178.00   0.50    1.43    --  107.32  45.00   0.00   50
 36  \w     79.00 104.00   0.50    1.43    --  107.32  30.00 -30.00   50
 37  \w    110.00 135.00   0.50    1.43    --  107.32  45.00   0.00   50
 38  \w    137.00 177.00   0.50    1.43    --  107.32  61.00 -30.00   80
 39  \w     35.00  84.00   0.50    1.43    --  107.32 -95.00   0.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix-Arc 100'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0421778000
_diffrn_orient_matrix_UB_12      -0.1212983000
_diffrn_orient_matrix_UB_13      0.0322422000
_diffrn_orient_matrix_UB_21      -0.0954952000
_diffrn_orient_matrix_UB_22      0.0033164000
_diffrn_orient_matrix_UB_23      0.0450238000
_diffrn_orient_matrix_UB_31      -0.0780237000
_diffrn_orient_matrix_UB_32      -0.0696462000
_diffrn_orient_matrix_UB_33      -0.0539785000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            29682
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.998
_diffrn_reflns_theta_min         4.014
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.126a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.229
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.00033(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         5308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0409P)^2^+0.6403P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0900
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4584
_reflns_number_total             5308
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05091j2.cif
_cod_data_source_block           rja250008_fa
_cod_depositor_comments
'Adding full bibliography for 7135067--7135068.cif.'
_cod_database_code               7135068
_chemical_oxdiff_formula         'C29 H29 N3 O4'
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.924
_diffrn_oxdiff_digest_frames
;
012b58b721093904059af7e8e5d1a384630342863fe
;
_diffrn_oxdiff_digest_hkl
;
01308354f459b2a053a1822c2d3faa74b4c52c
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
  C14(H14), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C)
;
_shelx_res_checksum              49677
_shelx_hkl_checksum              77002
_shelx_shelxl_version_number     2019/1
_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 1.375
_oxdiff_exptl_absorpt_empirical_full_min 0.762