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_1573029
_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         'C29 H27 Br N2 O2'
_chemical_formula_sum            'C29 H27 Br N2 O2'
_chemical_formula_weight         515.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-09-09
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.3491(3)
_cell_length_b                   9.93950(10)
_cell_length_c                   22.8671(3)
_cell_measurement_reflns_used    11395
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      76.8780
_cell_measurement_theta_min      4.3750
_cell_volume                     4852.38(11)
_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 0.997
_diffrn_measured_fraction_theta_max 0.937
_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     74.00 101.00   0.50    0.58    --   46.55 125.00 -90.00   54
  2  \w    132.00 178.00   0.50    2.32    --  108.12  45.00-150.00   92
  3  \w     97.00 123.00   0.50    2.32    --  108.12  45.00-150.00   52
  4  \w    -36.00  22.00   0.50    0.58    --   46.55 -19.00   0.00  116
  5  \w     18.00  51.00   0.50    2.32    --   97.16 -45.00 -60.00   66
  6  \w    -25.00   1.00   0.50    0.58    --   46.55 -16.00  97.00   52
  7  \w     31.00  56.00   0.50    2.32    --  108.12 -61.00   0.00   50
  8  \w     24.00  51.00   0.50    2.32    --   97.16 -45.00  30.00   54
  9  \w     22.00  48.00   0.50    2.32    --   97.16 -45.00 150.00   52
 10  \w    -11.00  15.00   0.50    0.58    --  -47.30  19.00 -60.00   52
 11  \w     69.00 107.00   0.50    2.32    --  108.12-111.00 -47.00   76
 12  \w     35.00  67.00   0.50    2.32    --  108.12-111.00 -47.00   64
 13  \w    -83.00 -56.00   0.50    2.32    --  -92.45 133.00 123.00   54
 14  \w   -105.00 -24.00   0.50    2.32    --  -92.45  77.00  60.00  162
 15  \w   -116.00 -79.00   0.50    2.32    --  -92.45 -16.00  97.00   74
 16  \w   -165.00-137.00   0.50    2.32    --  -92.45 -16.00  97.00   56
 17  \w   -125.00 -74.00   0.50    0.58    --  -47.30 -57.00  60.00  102
 18  \w    -58.00 -27.00   0.50    0.58    --  -47.30 -57.00  60.00   62
 19  \w    -56.00 -23.00   0.50    2.32    --  -92.45 -16.00  97.00   66
;
_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      -0.0009528000
_diffrn_orient_matrix_UB_12      0.0320742000
_diffrn_orient_matrix_UB_13      -0.0659023000
_diffrn_orient_matrix_UB_21      -0.0721670000
_diffrn_orient_matrix_UB_22      0.0007344000
_diffrn_orient_matrix_UB_23      0.0009788000
_diffrn_orient_matrix_UB_31      0.0005613000
_diffrn_orient_matrix_UB_32      0.1516224000
_diffrn_orient_matrix_UB_33      0.0139155000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20583
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.192
_diffrn_reflns_theta_min         3.866
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.535
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.703
_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    1.411
_exptl_crystal_description       plate
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4824
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.193
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0106P)^2^+8.7782P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0930
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4282
_reflns_number_total             4824
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04700a3.cif
_cod_data_source_block           rja240028_2_fa
_cod_database_code               1573029
_chemical_oxdiff_formula         'C29 H27 Br1 N2 O2'
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.593
_diffrn_oxdiff_digest_frames
;
01ad83d86606334a7d3e95cb1f9d02d34001356a9e2
;
_diffrn_oxdiff_digest_hkl
;
01c8b555d87d75017b3f9de374ea9f52471317
;
_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(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              17657
_shelx_hkl_checksum              38393
_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 1.305
_oxdiff_exptl_absorpt_empirical_full_min 0.712