Stereoselective synthesis of atropisomeric amides enabled by intramolecular acyl transfer.
Wootton, Jack M.; Roper, Natalie J.; Morris, Catrin E.; Maguire, Victoria E.; Duff, Lee C.; Waddell, Paul G.; Whitwood, Adrian C.; Gammons, Richard J.; Miah, Afjal H.; Lynam, Jason M.; Armstrong, Roly J.; Unsworth, William P.; Chemical science 16 (2025) 3938–3945; doi:10.1039/d4sc05760k

data_1573761
_publ_section_title
;
 Stereoselective synthesis of atropisomeric amides enabled by
 intramolecular acyl transfer.
;
_journal_issue                   9
_journal_name_full               'Chemical science'
_journal_page_first              3938
_journal_page_last               3945
_journal_paper_doi               10.1039/d4sc05760k
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C28 H28 N2 O2'
_chemical_formula_sum            'C28 H28 N2 O2'
_chemical_formula_weight         424.52
_chemical_name_systematic
N-(2-(tert-butyl)phenyl)-N-(1-phenyl-2-(pyridin-2-yl)ethyl)furan-2-carboxamide
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-08
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-06-17 deposited with the CCDC.	2025-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.442(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3156(3)
_cell_length_b                   15.8552(5)
_cell_length_c                   17.6204(6)
_cell_measurement_reflns_used    2118
_cell_measurement_temperature    110.2(2)
_cell_measurement_theta_max      76.6100
_cell_measurement_theta_min      3.7750
_cell_volume                     2277.00(14)
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.95a 64-bit (release 03-11-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.2(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -81.00   0.00   0.50    1.00    --  -48.64 105.00  51.00  162
  2  \w     51.00  76.00   0.50    1.00    --   48.64-105.00 -48.00   50
  3  \w     55.00  81.00   0.50    4.00    --  107.75-105.00 -48.00   52
  4  \w    121.00 176.00   0.50    4.00    --  107.75 105.00  51.00  110
  5  \w   -118.00 -75.00   0.50    1.00    --  -48.64-125.00-180.00   86
  6  \w   -107.00 -79.00   0.50    1.00    --  -48.64-125.00   0.00   56
  7  \w   -108.00 -73.00   0.50    1.00    --  -48.64-125.00 120.00   70
  8  \w   -117.00 -75.00   0.50    1.00    --  -48.64-125.00  30.00   84
  9  \w      2.00  81.00   0.50    1.00    --   48.64 -99.00-120.00  158
 10  \w     40.00 104.00   0.50    4.00    --  107.75 -99.00  30.00  128
 11  \w     38.00 112.00   0.50    4.00    --  107.75-125.00 -90.00  148
 12  \w     96.00 178.00   0.50    4.00    --  107.75  57.00-150.00  164
 13  \w     35.00  80.00   0.50    4.00    --  107.75 -37.00 -90.00   90
 14  \w     99.00 159.00   0.50    4.00    --  107.75  57.00-120.00  120
 15  \w     83.00 108.00   0.50    4.00    --  107.75 -37.00 -90.00   50
 16  \w     38.00  86.00   0.50    4.00    --  107.75 -99.00 120.00   96
 17  \w     72.00  97.00   0.50    4.00    --  107.75 -99.00   0.00   50
 18  \w     44.00  79.00   0.50    4.00    --  107.75-125.00-150.00   70
 19  \w     50.00 123.00   0.50    4.00    --  107.75 -57.00  90.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0463247000
_diffrn_orient_matrix_UB_12      0.0936531000
_diffrn_orient_matrix_UB_13      0.0130731000
_diffrn_orient_matrix_UB_21      -0.0843490000
_diffrn_orient_matrix_UB_22      0.0020443000
_diffrn_orient_matrix_UB_23      0.0703315000
_diffrn_orient_matrix_UB_31      0.1627132000
_diffrn_orient_matrix_UB_32      -0.0255674000
_diffrn_orient_matrix_UB_33      0.0533970000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13841
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.047
_diffrn_reflns_theta_max         67.047
_diffrn_reflns_theta_min         3.785
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       plate
_exptl_crystal_F_000             904
_exptl_crystal_recrystallization_method
'dichloromethane and hexane slow evaporation'
_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.059
_exptl_crystal_size_min          0.049
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.00102(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         4055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0391P)^2^+0.5220P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0819
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3554
_reflns_number_total             4055
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc05760k2.cif
_cod_data_source_block           wpu23016
_cod_depositor_comments
'Adding full bibliography for 1573760--1573765.cif.'
_cod_original_cell_volume        2277.00(13)
_cod_database_code               1573761
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C28 H28 N2 O2'
_chemical_oxdiff_usercomment     'Jack Wooton Jmw11-064-P'
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.908
_olex2_refinement_description
;
;
_shelx_res_checksum              61873
_shelx_hkl_checksum              51686
_olex2_date_sample_submission    2023-11-07
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id Jmw11-064-P
_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 1.293
_oxdiff_exptl_absorpt_empirical_full_min 0.734