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_1573030
_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 H34 N2 O2'
_chemical_formula_sum            'C29 H34 N2 O2'
_chemical_formula_weight         442.58
_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             2023-07-21
_audit_creation_method
;
Olex2 1.5-ac5-023
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-05-15 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                85.525(2)
_cell_angle_beta                 78.490(2)
_cell_angle_gamma                68.897(3)
_cell_formula_units_Z            4
_cell_length_a                   10.2249(3)
_cell_length_b                   12.0964(3)
_cell_length_c                   22.9051(4)
_cell_measurement_reflns_used    20081
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      77.7740
_cell_measurement_theta_min      1.9640
_cell_volume                     2589.80(12)
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.926
_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     58.00  84.00   0.50    3.00    --   48.76-149.00-111.00   52
  2  \w     76.00 121.00   0.50    3.00    --   48.76 123.00 131.00   90
  3  \w     33.00  58.00   0.50    3.00    --   48.76-123.00  51.00   50
  4  \w     64.00  89.00   0.50    3.00    --   48.76 149.00 -65.00   50
  5  \w   -122.00 -77.00   0.50    3.00    --  -49.76-123.00  51.00   90
  6  \w   -111.00 -60.00   0.50    3.00    --  -49.76 149.00 -65.00  102
  7  \w    -81.00 -56.00   0.50    3.00    --  -49.76 123.00 131.00   50
  8  \w    -83.00 -57.00   0.50    3.00    --  -49.76-149.00-111.00   52
  9  \w   -134.00-109.00   0.50    3.00    --  -92.01-149.00-111.00   50
 10  \w   -129.00 -25.00   0.50    3.00    --  -92.01 149.00 -65.00  208
 11  \w    -89.00 -64.00   0.50    3.00    --  -92.01 123.00 131.00   50
 12  \w   -135.00-110.00   0.50    3.00    --  -92.01-123.00  51.00   50
 13  \w     86.00 112.00   0.50    3.00    --   96.11 149.00 -65.00   52
 14  \w     43.00  68.00   0.50    3.00    --   96.11-123.00  51.00   50
 15  \w     97.00 122.00   0.50    3.00    --   96.11 123.00 131.00   50
 16  \w     53.00  78.00   0.50    3.00    --   96.11-149.00-111.00   50
 17  \w    102.00 127.00   0.50    3.00    --  108.00 123.00 131.00   50
 18  \w     49.00  74.00   0.50    3.00    --  108.00-123.00  51.00   50
 19  \w     59.00  84.00   0.50    3.00    --  108.00-149.00-111.00   50
 20  \w     88.00 113.00   0.50    3.00    --  108.00 149.00 -65.00   50
 21  \w    -29.00  26.00   0.50    3.00    --   48.76 -19.00 -30.00  110
 22  \w     81.00 120.00   0.50    3.00    --   48.76 125.00  30.00   78
 23  \w    -28.00  15.00   0.50    3.00    --   48.76 -19.00 -60.00   86
 24  \w    -27.00  28.00   0.50    3.00    --  -49.76  19.00-150.00  110
 25  \w    -27.00  29.00   0.50    3.00    --  -49.76  19.00 -30.00  112
 26  \w   -102.00 -28.00   0.50    3.00    --  -92.01  77.00  30.00  148
 27  \w   -167.00 -75.00   0.50    3.00    --  -92.01 -45.00-120.00  184
 28  \w    -78.00 -30.00   0.50    3.00    --  -92.01 125.00 -90.00   96
 29  \w   -162.00 -72.00   0.50    3.00    --  -92.01 -61.00 120.00  180
 30  \w    -43.00 -18.00   0.50    3.00    --  -92.01  45.00 120.00   50
 31  \w    -51.00 -14.00   0.50    3.00    --  -92.01  45.00  90.00   74
 32  \w   -149.00 -85.00   0.50    3.00    --  -92.01 -95.00   0.00  128
 33  \w     18.00  46.00   0.50    3.00    --   96.11 -45.00-180.00   56
 34  \w    108.00 134.00   0.50    3.00    --   96.11  45.00 -60.00   52
 35  \w     20.00  51.00   0.50    3.00    --   96.11 -45.00 -60.00   62
 36  \w     32.00  70.00   0.50    3.00    --   96.11 -61.00-150.00   76
 37  \w     62.00  98.00   0.50    3.00    --   96.11 -77.00  30.00   72
 38  \w   -107.00 -32.00   0.50    3.00    --  -99.00 107.00 -96.17  150
 39  \w   -125.00 -30.00   0.50    3.00    --  -99.00 143.00 102.21  190
 40  \w     39.00  95.00   0.50    3.00    --  108.00 -95.00-150.00  112
 41  \w     60.00  86.00   0.50    3.00    --  108.00 -77.00-120.00   52
 42  \w     41.00 100.00   0.50    3.00    --  108.00 -95.00  30.00  118
 43  \w     37.00  62.00   0.50    3.00    --  108.00 -61.00  90.00   50
 44  \w     93.00 177.00   0.50    3.00    --  108.00  45.00-150.00  168
 45  \w     76.00 102.00   0.50    3.00    --  108.00 -95.00  90.00   52
 46  \w     36.00  64.00   0.50    3.00    --  108.00 -61.00  60.00   56
;
_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      -0.0402042000
_diffrn_orient_matrix_UB_12      0.1354042000
_diffrn_orient_matrix_UB_13      0.0019286000
_diffrn_orient_matrix_UB_21      0.0155606000
_diffrn_orient_matrix_UB_22      0.0061433000
_diffrn_orient_matrix_UB_23      -0.0683591000
_diffrn_orient_matrix_UB_31      -0.1585595000
_diffrn_orient_matrix_UB_32      0.0161524000
_diffrn_orient_matrix_UB_33      0.0059147000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            36406
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.649
_diffrn_reflns_theta_min         1.968
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.553
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
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    1.135
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.00118(10)
_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   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     614
_refine_ls_number_reflns         10308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0315P)^2^+0.6579P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0905
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9166
_reflns_number_total             10308
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04700a3.cif
_cod_data_source_block           rja230009_fa
_cod_database_code               1573030
_chemical_oxdiff_formula         'C29 H34 N2 O2'
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.869
_diffrn_oxdiff_digest_frames
;
01db3cf9cf59dd313d49b983892f99f4d203918f667
;
_diffrn_oxdiff_digest_hkl
;
01ae99b6a3cd089288c7a568db66282aea2ea4
;
_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:
 C2(H2A), C31(H31)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C34(H34), C35(H35),
  C36(H36), C37(H37), C38(H38), C41(H41), C42(H42), C43(H43), C44(H44),
 C50(H50), C51(H51), C52(H52), C53(H53), C54(H54)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C27(H27A,H27B,
 H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C46(H46A,H46B,H46C), C47(H47A,
 H47B,H47C), C48(H48A,H48B,H48C), C56(H56A,H56B,H56C), C57(H57A,H57B,H57C),
 C58(H58A,H58B,H58C)
;
_shelx_res_checksum              8699
_shelx_hkl_checksum              77461
_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 1.402
_oxdiff_exptl_absorpt_empirical_full_min 0.587