A stereodivergent multicomponent approach for the synthesis of C-N atropisomeric peptide analogues.
Roper, Natalie J.; Campbell, Aaron D. G.; Waddell, Paul G.; Brown, Alistair K.; Ermanis, Kristaps; Armstrong, Roly J.; Chemical science 15 (2024) 16743–16751; doi:10.1039/d4sc04700a

data_1573027
_publ_section_title
;
 A stereodivergent multicomponent approach for the synthesis of C-N
 atropisomeric peptide analogues.
;
_journal_issue                   40
_journal_name_full               'Chemical science'
_journal_page_first              16743
_journal_page_last               16751
_journal_paper_doi               10.1039/d4sc04700a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C33 H34 N2 O2'
_chemical_formula_sum            'C33 H34 N2 O2'
_chemical_formula_weight         490.62
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-09-10
_audit_creation_method
;
Olex2 1.5-ac5-023
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-09-10 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                95.4770(10)
_cell_angle_beta                 94.5580(10)
_cell_angle_gamma                109.670(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6100(2)
_cell_length_b                   9.7457(2)
_cell_length_c                   15.6810(3)
_cell_measurement_reflns_used    12839
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      75.4440
_cell_measurement_theta_min      2.8620
_cell_volume                     1366.82(5)
_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  '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 0.913
_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     55.00 105.00   0.50    0.61    --  108.12 -77.00 120.00  100
  2  \w     35.00 105.00   0.50    0.61    --  108.12 -95.00  30.00  140
  3  \w     24.00 105.00   0.50    0.61    --   97.16 -95.00 -30.00  162
  4  \w     31.00  71.00   0.50    0.61    --  108.12 -61.00 -90.00   80
  5  \w     16.00  51.00   0.50    0.61    --   97.16 -45.00-180.00   70
  6  \w     77.00 178.00   0.50    0.61    --  108.12  77.00-120.00  202
  7  \w     77.00 178.00   0.50    0.61    --  108.12  77.00-120.00  202
  8  \w     74.00 173.00   0.50    0.61    --   97.16 125.00-120.00  198
  9  \w     17.00  43.00   0.50    0.15    --   54.00  88.00 -89.85   52
 10  \w     16.00  43.00   0.50    0.15    --   54.00  89.00 -45.27   54
 11  \w    -48.00 -15.00   0.50    0.15    --   14.00 129.00 -53.02   66
 12  \w    -43.00  35.00   0.50    0.15    --  -47.30  38.00-180.00  156
 13  \w    -51.00 -11.00   0.50    0.61    --  -92.45  45.00   0.00   80
 14  \w    -51.00 -11.00   0.50    0.61    --  -92.45  45.00  30.00   80
 15  \w    -71.00 -15.00   0.50    0.61    --  -92.45  61.00 120.00  112
 16  \w   -112.00 -16.00   0.50    0.61    --  -92.45 125.00 120.00  192
 17  \w   -112.00 -16.00   0.50    0.61    --  -92.45 125.00 120.00  192
 18  \w   -152.00 -51.00   0.50    0.61    --  -78.00 -68.00  21.35  202
 19  \w   -166.00 -64.00   0.50    0.61    --  -90.00 -65.00  45.33  204
 20  \w   -152.00 -51.00   0.50    0.61    --  -78.00 -68.00  21.35  202
 21  \w   -158.00 -56.00   0.50    0.61    --  -86.00 -74.00 -43.71  204
 22  \w   -130.00  19.00   0.50    0.15    --  -47.30 -19.00   0.00  298
 23  \w   -121.00 -23.00   0.50    0.61    --  -99.00 138.00-151.67  196
 24  \w   -166.00 -64.00   0.50    0.61    --  -90.00 -65.00  45.33  204
 25  \w   -168.00 -73.00   0.50    0.61    --  -92.45-125.00  90.00  190
 26  \w   -166.00 -83.00   0.50    0.61    --  -92.45 -95.00  90.00  166
 27  \w   -166.00 -83.00   0.50    0.61    --  -92.45 -95.00-180.00  166
;
_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      0.1351535000
_diffrn_orient_matrix_UB_12      -0.0326957000
_diffrn_orient_matrix_UB_13      0.0402362000
_diffrn_orient_matrix_UB_21      -0.0836845000
_diffrn_orient_matrix_UB_22      -0.0519672000
_diffrn_orient_matrix_UB_23      0.0773694000
_diffrn_orient_matrix_UB_31      -0.0642614000
_diffrn_orient_matrix_UB_32      -0.1577881000
_diffrn_orient_matrix_UB_33      -0.0477033000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20367
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.454
_diffrn_reflns_theta_min         2.851
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.954
_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    1.192
_exptl_crystal_description       prism
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0024(3)
_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   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0361
_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^)+(0.0405P)^2^+0.4076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0944
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4800
_reflns_number_total             5299
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04700a3.cif
_cod_data_source_block           rja240026_fa
_cod_database_code               1573027
_chemical_oxdiff_formula         'C33 H34 N2 O2'
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.939
_diffrn_oxdiff_digest_frames
;
01399655a3b6f0558372be6fada5d7386904170bd0d
;
_diffrn_oxdiff_digest_hkl
;
011f43bb7b66decf5bb7005394145ed1974032
;
_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:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C22(H22), C24(H24), C27(H27), C28(H28), C29(H29), C30(H30),
  C31(H31)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C32(H32A,H32B,
 H32C), C33(H33A,H33B,H33C)
;
_shelx_res_checksum              74119
_shelx_hkl_checksum              63426
_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 1.124
_oxdiff_exptl_absorpt_empirical_full_min 0.821