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_1573762
_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         'C30 H30 N2 O'
_chemical_formula_sum            'C30 H30 N2 O'
_chemical_formula_weight         434.56
_chemical_melting_point          394(2)
_chemical_name_systematic
N-(2-(tert-butyl)phenyl)-N-(1-phenyl-2-(pyridin-2-yl)ethyl)benzamide
_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             2023-11-06
_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                 104.1645(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.85289(15)
_cell_length_b                   23.3855(3)
_cell_length_c                   8.96547(10)
_cell_measurement_reflns_used    16405
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      76.7940
_cell_measurement_theta_min      3.7630
_cell_volume                     2409.55(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.94a 64-bit (release 20-10-2023))'
_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      110.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -72.00  24.00   0.50    0.25    --  -48.64  80.00-115.00  192
  2  \w    -72.00  24.00   0.50    0.25    --  -48.64  80.00-115.00  192
  3  \w     35.00 132.00   0.50    1.00    --  107.75 -80.00 120.00  194
  4  \w    101.00 178.00   0.50    1.00    --  107.75  80.00-115.00  154
  5  \w   -118.00 -73.00   0.50    0.25    --  -48.64-125.00 -90.00   90
  6  \w   -118.00 -73.00   0.50    0.25    --  -48.64-125.00-150.00   90
  7  \w   -118.00 -73.00   0.50    0.25    --  -48.64-125.00-120.00   90
  8  \w   -118.00 -73.00   0.50    0.25    --  -48.64-125.00  90.00   90
  9  \w   -118.00 -73.00   0.50    0.25    --  -48.64-125.00   0.00   90
 10  \w    -21.00  73.00   0.50    0.25    --   48.64 -80.00 120.00  188
 11  \w     -1.00  81.00   0.50    0.25    --   48.64 -99.00  60.00  164
 12  \w     32.00 121.00   0.50    1.00    --  107.75 -19.00-120.00  178
 13  \w     95.00 178.00   0.50    1.00    --  107.75  19.00-120.00  166
 14  \w     95.00 178.00   0.50    1.00    --  107.75  19.00-180.00  166
 15  \w     37.00 114.00   0.50    1.00    --  107.75 -37.00-150.00  154
 16  \w     75.00 121.00   0.50    1.00    --  107.75 -19.00 120.00   92
 17  \w     36.00  82.00   0.50    1.00    --  107.75 -37.00 -30.00   92
 18  \w     86.00 120.00   0.50    1.00    --  107.75 -37.00 -30.00   68
 19  \w     43.00 106.00   0.50    1.00    --  107.75 -99.00-180.00  126
 20  \w     41.00  66.00   0.50    1.00    --  107.75 -19.00 120.00   50
 21  \w     40.00  65.00   0.50    1.00    --  107.75 -37.00-150.00   50
 22  \w     41.00  81.00   0.50    1.00    --  107.75 -99.00 -90.00   80
 23  \w     94.00 120.00   0.50    1.00    --  107.75 -80.00 120.00   52
;
_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      0.0502690000
_diffrn_orient_matrix_UB_12      -0.0562947000
_diffrn_orient_matrix_UB_13      0.0780590000
_diffrn_orient_matrix_UB_21      -0.0990877000
_diffrn_orient_matrix_UB_22      -0.0027403000
_diffrn_orient_matrix_UB_23      0.0835009000
_diffrn_orient_matrix_UB_31      -0.0749683000
_diffrn_orient_matrix_UB_32      -0.0340945000
_diffrn_orient_matrix_UB_33      -0.1354519000
_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  0.0284
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            22033
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         3.780
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.559
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.801
_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    1.198
_exptl_crystal_description       irregular
_exptl_crystal_F_000             928
_exptl_crystal_recrystallization_method 'Hexane slow evaporation'
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.143
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.00129(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   1.036
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         4305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0349
_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^)+(0.0426P)^2^+0.8644P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0912
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3959
_reflns_number_total             4305
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc05760k2.cif
_cod_data_source_block           wpu23015
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '392-396' was changed to
'394(2)' -- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1573760--1573765.cif.
;
_cod_database_code               1573762
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C30 H30 N2 O1'
_chemical_oxdiff_usercomment     'Jack Wootton JMW11-059-p'
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.863
_olex2_refinement_description
;
;
_shelx_res_checksum              72151
_shelx_hkl_checksum              75238
_olex2_date_sample_data_collection 2023-11-03
_olex2_date_sample_submission    2023-10-27
_olex2_exptl_crystal_mounting_method 'Oil on 200 micrometre micromount'
_olex2_submission_original_sample_id Jmw11-059-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 1.336
_oxdiff_exptl_absorpt_empirical_full_min 0.729