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_1573028
_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         'C30 H30 N2 O2'
_chemical_formula_sum            'C30 H30 N2 O2'
_chemical_formula_weight         450.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90
_cell_angle_beta                 103.4340(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.91490(10)
_cell_length_b                   20.5392(2)
_cell_length_c                   11.46750(10)
_cell_measurement_reflns_used    11927
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      76.4690
_cell_measurement_theta_min      4.1430
_cell_volume                     2500.48(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  '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 0.919
_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     21.00  65.00   0.50    0.75    --   97.16 -61.00-120.00   88
  2  \w     40.00  67.00   0.50    0.75    --  108.12 -65.00 -58.00   54
  3  \w     34.00  70.00   0.50    0.75    --   97.16 -65.00 -58.00   72
  4  \w     17.00  42.00   0.50    0.75    --   97.16 -45.00 -30.00   50
  5  \w    -29.00  70.00   0.50    0.75    --   46.55 -65.00 -58.00  198
  6  \w     26.00  51.00   0.50    0.75    --   97.16 -45.00   0.00   50
  7  \w     33.00  70.00   0.50    0.75    --  108.12 -61.00  60.00   74
  8  \w     26.00  69.00   0.50    0.75    --   97.16 -61.00 120.00   86
  9  \w     98.00 123.00   0.50    0.75    --   97.16  65.00  77.00   50
 10  \w    109.00 157.00   0.50    0.75    --  108.12  65.00  77.00   96
 11  \w     76.00 102.00   0.50    0.75    --   46.55 125.00 -30.00   52
 12  \w     25.00 107.00   0.50    0.75    --   46.55  65.00  77.00  164
 13  \w     66.00 147.00   0.50    0.75    --   97.16  77.00   0.00  162
 14  \w     49.00  93.00   0.50    0.75    --  108.12 -95.00-150.00   88
 15  \w    -78.00 -31.00   0.50    0.75    --  -92.45  65.00  77.00   94
 16  \w    -71.00 -18.00   0.50    0.75    --  -92.45  61.00 150.00  106
 17  \w    -49.00 -12.00   0.50    0.75    --  -92.45  45.00  60.00   74
 18  \w    -45.00 -12.00   0.50    0.75    --  -92.45  45.00 -90.00   66
 19  \w    -48.00 -22.00   0.50    0.75    --  -92.45  45.00-150.00   52
 20  \w   -170.00-117.00   0.50    0.75    --  -92.45 -45.00-180.00  106
 21  \w   -168.00 -72.00   0.50    0.75    --  -92.45 -65.00 -58.00  192
 22  \w   -123.00 -73.00   0.50    0.75    --  -47.30-125.00  30.00  100
 23  \w    -96.00 -71.00   0.50    0.75    --  -47.30 -65.00 -58.00   50
 24  \w   -114.00 -73.00   0.50    0.75    --  -92.45 -45.00-180.00   82
;
_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      -0.0214882000
_diffrn_orient_matrix_UB_12      0.0557318000
_diffrn_orient_matrix_UB_13      0.0829153000
_diffrn_orient_matrix_UB_21      -0.1350614000
_diffrn_orient_matrix_UB_22      0.0088430000
_diffrn_orient_matrix_UB_23      -0.0763543000
_diffrn_orient_matrix_UB_31      -0.0483895000
_diffrn_orient_matrix_UB_32      -0.0494529000
_diffrn_orient_matrix_UB_33      0.0798504000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18656
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.966
_diffrn_reflns_theta_min         4.164
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.928
_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    1.197
_exptl_crystal_description       prism
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.00128(16)
_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   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0441P)^2^+0.7221P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0960
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4280
_reflns_number_total             4856
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04700a3.cif
_cod_data_source_block           rja240027_fa
_cod_database_code               1573028
_chemical_oxdiff_formula         'C30 H30 N2 O2'
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.907
_diffrn_oxdiff_digest_frames
;
0193a265159504872411a7417989b875350220607ae
;
_diffrn_oxdiff_digest_hkl
;
016ed5d07cacaa0a1a188820552758e35221ad
;
_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:
 C19(H19)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C15(H15), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C)
;
_shelx_res_checksum              18427
_shelx_hkl_checksum              5621
_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 1.261
_oxdiff_exptl_absorpt_empirical_full_min 0.761