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_7135067
_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           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-08-07
_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                 106.868(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4876(2)
_cell_length_b                   12.9087(2)
_cell_length_c                   17.8682(3)
_cell_measurement_reflns_used    14022
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      76.5340
_cell_measurement_theta_min      4.0980
_cell_volume                     2535.67(8)
_computing_cell_refinement       'CrysAlisPro 1.171.43.126a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.126a (Rigaku OD, 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  'SHELXL 2019/1 (Sheldrick, 2015)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.940
_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     31.00  61.00   0.50    0.60    --  108.12 -61.00 120.00   60
  2  \w     45.00  92.00   0.50    0.60    --  108.12 -77.00  60.00   94
  3  \w     43.00  70.00   0.50    0.60    --  108.12 -61.00   0.00   54
  4  \w     19.00  45.00   0.50    0.60    --   97.16 -45.00  30.00   52
  5  \w     30.00  60.00   0.50    0.60    --  108.12 -53.00 150.00   60
  6  \w     18.00  60.00   0.50    0.60    --   97.16 -53.00 150.00   84
  7  \w     18.00  44.00   0.50    0.60    --   97.16 -45.00 -30.00   52
  8  \w     17.00  46.00   0.50    0.60    --   97.16 -45.00 -60.00   58
  9  \w     41.00  68.00   0.50    0.60    --   97.16 -61.00 -90.00   54
 10  \w     33.00  71.00   0.50    0.60    --  108.12 -61.00-150.00   76
 11  \w     85.00 169.00   0.50    0.60    --  108.12  61.00-150.00  168
 12  \w     88.00 132.00   0.50    0.60    --  108.12  53.00 -65.00   88
 13  \w     74.00 176.00   0.50    0.60    --   97.16  53.00 -65.00  204
 14  \w     23.00 126.00   0.50    0.60    --   46.30  53.00 -65.00  206
 15  \w    -35.00  26.00   0.50    0.60    --   46.30 -19.00   0.00  122
 16  \w    -33.00  60.00   0.50    0.60    --   46.30 -53.00 150.00  186
 17  \w     76.00 119.00   0.50    0.60    --   46.30 125.00   0.00   86
 18  \w     74.00 121.00   0.50    0.60    --   46.30 125.00-150.00   94
 19  \w    -60.00  32.00   0.50    0.60    --  -47.11  53.00 -65.00  184
 20  \w    -49.00 -12.00   0.50    0.60    --  -92.45  45.00 -90.00   74
 21  \w    -60.00 -13.00   0.50    0.60    --  -92.45  53.00 -65.00   94
 22  \w    -49.00 -20.00   0.50    0.60    --  -92.45  45.00-120.00   58
 23  \w    -50.00 -12.00   0.50    0.60    --  -92.45  45.00   0.00   76
 24  \w    -51.00 -12.00   0.50    0.60    --  -92.45  45.00  60.00   78
 25  \w    -49.00 -23.00   0.50    0.60    --  -92.45  45.00 120.00   52
 26  \w   -108.00 -75.00   0.50    0.60    --  -92.45 -45.00  30.00   66
 27  \w   -172.00-118.00   0.50    0.60    --  -92.45 -45.00  30.00  108
 28  \w   -126.00 -24.00   0.50    0.60    --  -47.11 -53.00 150.00  204
 29  \w   -172.00 -69.00   0.50    0.60    --  -92.45 -53.00 150.00  206
;
_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      -0.0327952000
_diffrn_orient_matrix_UB_12      0.0569763000
_diffrn_orient_matrix_UB_13      0.0669383000
_diffrn_orient_matrix_UB_21      0.1263778000
_diffrn_orient_matrix_UB_22      0.0515554000
_diffrn_orient_matrix_UB_23      0.0240048000
_diffrn_orient_matrix_UB_31      -0.0508889000
_diffrn_orient_matrix_UB_32      0.0913022000
_diffrn_orient_matrix_UB_33      -0.0552949000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            24269
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.879
_diffrn_reflns_theta_min         4.101
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.920
_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    1.267
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.00069(15)
_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   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         5033
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0552P)^2^+0.7363P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1088
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4274
_reflns_number_total             5033
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05091j2.cif
_cod_data_source_block           rja240024_fa
_cod_depositor_comments
'Adding full bibliography for 7135067--7135068.cif.'
_cod_database_code               7135067
_chemical_oxdiff_formula         'C29 H29 N3 O4'
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.886
_diffrn_oxdiff_digest_frames
;
015bc7fc136df4ec07aa52858ea8d5339b02998da35
;
_diffrn_oxdiff_digest_hkl
;
01adac99603dc30ff71b16a891361bffa77e4a
;
_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),
  C13(H13), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
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              15023
_shelx_hkl_checksum              76774
_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 1.235
_oxdiff_exptl_absorpt_empirical_full_min 0.784