Synthesis, structure and stereodynamics of atropisomeric <i>N</i>-chloroamides.
Campbell, Aaron D. G.; Roper, Natalie J.; Waddell, Paul G.; Wills, Corinne; Dixon, Casey M.; Denton, Ross M.; Ermanis, Kristaps; Armstrong, Roly J.; Chemical communications (Cambridge, England) 60 (2024) 3818–3821; doi:10.1039/d4cc00268g

data_7132810
_publ_section_title
;
 Synthesis, structure and stereodynamics of atropisomeric
 <i>N</i>-chloroamides.
;
_journal_issue                   28
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3818
_journal_page_last               3821
_journal_paper_doi               10.1039/d4cc00268g
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C18 H20 Cl N O2'
_chemical_formula_sum            'C18 H20 Cl N O2'
_chemical_formula_weight         317.80
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-01
_audit_creation_method
;
Olex2 1.5-ac5-023
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2023-11-13 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                77.9650(10)
_cell_angle_beta                 76.1000(10)
_cell_angle_gamma                77.2070(10)
_cell_formula_units_Z            4
_cell_length_a                   8.35130(10)
_cell_length_b                   13.4596(2)
_cell_length_c                   15.5830(2)
_cell_measurement_reflns_used    24066
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      78.2000
_cell_measurement_theta_min      3.0010
_cell_volume                     1635.64(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.914
_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     39.00  70.00   0.50    0.26    --   48.76-143.00  55.00   62
  2  \w     50.00  75.00   0.50    0.26    --   96.11-143.00  55.00   50
  3  \w     49.00 125.00   0.50    0.26    --  108.00-143.00  55.00  152
  4  \w     36.00  61.00   0.50    0.26    --   48.76-128.00-133.00   50
  5  \w     50.00  75.00   0.50    0.26    --  108.00-128.00-133.00   50
  6  \w     62.00 110.00   0.50    0.26    --  108.00-125.00-180.00   96
  7  \w     61.00  98.00   0.50    0.26    --  108.00 -77.00-180.00   74
  8  \w     25.00  65.00   0.50    0.26    --   96.11 -61.00-150.00   80
  9  \w     42.00  69.00   0.50    0.26    --  108.00 -61.00-120.00   54
 10  \w     48.00  96.00   0.50    0.26    --  108.00 -77.00  30.00   96
 11  \w     35.00  61.00   0.50    0.26    --  108.00 -61.00   0.00   52
 12  \w     34.00  59.00   0.50    0.26    --  108.00 -61.00  60.00   50
 13  \w     91.00 116.00   0.50    0.26    --   96.11 143.00 111.00   50
 14  \w     92.00 117.00   0.50    0.26    --  108.00 143.00 111.00   50
 15  \w    101.00 126.00   0.50    0.26    --  108.00 128.00 -59.00   50
 16  \w    111.00 136.00   0.50    0.26    --   96.11 128.00 -59.00   50
 17  \w     40.00  66.00   0.50    0.26    --   62.00  71.00 -32.16   52
 18  \w     31.00  56.00   0.50    0.26    --   58.00  77.00 -88.43   50
 19  \w     32.00  58.00   0.50    0.26    --   58.00  77.00-119.04   52
 20  \w     31.00  56.00   0.50    0.26    --   58.00  77.00-170.46   50
 21  \w     70.00 154.00   0.50    0.26    --   96.11  77.00-180.00  168
 22  \w     85.00 111.00   0.50    0.26    --   58.00  77.00-119.04   52
 23  \w     33.00  62.00   0.50    0.26    --   58.00  76.00  21.19   58
 24  \w     36.00  62.00   0.50    0.26    --   62.00  76.00 156.91   52
 25  \w     31.00  57.00   0.50    0.26    --   58.00  77.00  85.57   52
 26  \w     69.00 126.00   0.50    0.26    --   58.00  77.00  85.57  114
 27  \w     96.00 122.00   0.50    0.26    --   62.00  75.00-156.55   52
 28  \w     38.00  64.00   0.50    0.26    --   62.00  75.00-156.55   52
 29  \w     38.00  64.00   0.50    0.26    --   58.00  75.00 -13.56   52
 30  \w     17.00  42.00   0.50    0.26    --   50.00  88.00  11.25   50
 31  \w     62.00 105.00   0.50    0.26    --   48.76 143.00 111.00   86
 32  \w    -43.00 -13.00   0.50    0.26    --   10.00 124.00 123.79   60
 33  \w    -25.00   1.00   0.50    0.26    --   18.00 104.00  45.42   52
 34  \w     15.00  41.00   0.50    0.26    --   50.00  92.00  43.29   52
 35  \w     16.00  42.00   0.50    0.26    --   50.00  91.00 111.83   52
 36  \w     -6.00  22.00   0.50    0.26    --   34.00 100.00 145.25   56
 37  \w    -60.00 -31.00   0.50    0.26    --   18.00 160.00 -46.45   58
 38  \w    -60.00 -33.00   0.50    0.26    --   18.00 162.00-116.83   54
 39  \w     16.00  41.00   0.50    0.26    --   50.00  89.00-129.59   50
 40  \w     17.00  42.00   0.50    0.26    --   50.00  88.00 -52.42   50
 41  \w   -110.00 -59.00   0.50    0.26    --  -49.76 143.00 111.00  102
 42  \w   -117.00 -73.00   0.50    0.26    --  -92.01 143.00 111.00   88
 43  \w    -85.00 -60.00   0.50    0.26    --  -49.76 128.00 -59.00   50
 44  \w    -90.00 -65.00   0.50    0.26    --  -92.01 128.00 -59.00   50
 45  \w   -104.00 -29.00   0.50    0.26    --  -92.01  77.00 -30.00  150
 46  \w    -48.00 -21.00   0.50    0.26    --  -92.01  45.00 -30.00   54
 47  \w   -105.00 -23.00   0.50    0.26    --  -92.01  77.00 120.00  164
 48  \w    -90.00 -64.00   0.50    0.26    --  -90.00 -77.00  97.03   52
 49  \w   -145.00 -67.00   0.50    0.26    --  -92.01 -77.00  90.00  156
 50  \w   -130.00 -92.00   0.50    0.26    --  -62.00 -77.00  71.40   76
 51  \w    -74.00 -35.00   0.50    0.26    --  -62.00 -77.00  71.40   78
 52  \w    -91.00 -66.00   0.50    0.26    --  -92.01 -77.00  30.00   50
 53  \w   -156.00 -65.00   0.50    0.26    --  -92.01 -77.00 -30.00  182
 54  \w   -141.00-116.00   0.50    0.26    --  -92.01 -77.00  30.00   50
 55  \w   -160.00 -65.00   0.50    0.26    --  -92.01 -77.00 -60.00  190
 56  \w   -160.00 -99.00   0.50    0.26    --  -92.01 -77.00 -90.00  122
 57  \w    -92.00 -66.00   0.50    0.26    --  -92.01 -77.00 -90.00   52
 58  \w   -126.00 -66.00   0.50    0.26    --  -92.01 -77.00-120.00  120
 59  \w   -146.00-103.00   0.50    0.26    --  -78.00 -76.00  46.39   86
 60  \w   -159.00 -67.00   0.50    0.26    --  -92.01 -77.00  60.00  184
 61  \w    -75.00 -48.00   0.50    0.26    --  -74.00 -75.00  52.28   54
 62  \w    -98.00 -53.00   0.50    0.26    --  -78.00 -76.00  46.39   90
 63  \w    -92.00 -67.00   0.50    0.26    --  -92.01 -77.00 120.00   50
 64  \w   -160.00 -97.00   0.50    0.26    --  -92.01 -77.00 120.00  126
 65  \w   -148.00-122.00   0.50    0.26    --  -82.00 -74.00 -13.32   52
 66  \w    -85.00 -57.00   0.50    0.26    --  -82.00 -73.00 108.80   56
 67  \w    -94.00 -62.00   0.50    0.26    --  -86.00 -71.00  24.43   64
 68  \w    -76.00 -51.00   0.50    0.26    --  -74.00 -68.00 134.33   50
 69  \w    -95.00 -43.00   0.50    0.26    --  -66.00 -70.00 -22.03  104
 70  \w    -91.00 -57.00   0.50    0.26    --  -82.00 -74.00 -13.32   68
 71  \w   -103.00 -68.00   0.50    0.26    --  -90.00 -70.00-166.42   70
 72  \w   -165.00 -79.00   0.50    0.26    --  -99.00 -69.00  13.30  172
 73  \w    -82.00 -56.00   0.50    0.26    --  -78.00 -67.00 119.62   52
 74  \w    -87.00 -61.00   0.50    0.26    --  -82.00 -67.00 113.95   52
 75  \w    -84.00 -57.00   0.50    0.26    --  -78.00 -67.00 155.09   54
 76  \w   -159.00 -68.00   0.50    0.26    --  -90.00 -67.00 148.18  182
 77  \w    -88.00 -58.00   0.50    0.26    --  -78.00 -66.00  -9.30   60
 78  \w    -88.00 -57.00   0.50    0.26    --  -78.00 -64.00 -54.56   62
 79  \w    -88.00 -53.00   0.50    0.26    --  -74.00 -64.00 -91.18   70
 80  \w    -77.00 -51.00   0.50    0.26    --  -70.00 -65.00-122.51   52
 81  \w    -77.00 -52.00   0.50    0.26    --  -74.00 -66.00-175.07   50
 82  \w    -83.00 -57.00   0.50    0.26    --  -78.00 -64.00-147.16   52
 83  \w    -82.00 -57.00   0.50    0.26    --  -78.00 -64.00-105.81   50
 84  \w    -91.00 -65.00   0.50    0.26    --  -86.00 -64.00-165.72   52
 85  \w   -137.00-111.00   0.50    0.26    --  -74.00 -66.00-175.07   52
 86  \w   -130.00-105.00   0.50    0.26    --  -74.00 -64.00 -91.18   50
 87  \w   -151.00 -92.00   0.50    0.26    --  -78.00 -64.00 -54.56  118
 88  \w   -153.00 -66.00   0.50    0.26    --  -86.00 -64.00 169.97  174
 89  \w   -116.00 -91.00   0.50    0.26    --  -49.76-143.00  55.00   50
 90  \w   -149.00 -69.00   0.50    0.26    --  -92.01-143.00  55.00  160
 91  \w   -158.00 -88.00   0.50    0.26    --  -92.01-128.00-133.00  140
 92  \w   -122.00 -97.00   0.50    0.26    --  -49.76-128.00-133.00   50
;
_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      0.0490667000
_diffrn_orient_matrix_UB_12      -0.1142968000
_diffrn_orient_matrix_UB_13      -0.0119878000
_diffrn_orient_matrix_UB_21      0.0232364000
_diffrn_orient_matrix_UB_22      0.0328562000
_diffrn_orient_matrix_UB_23      -0.1023762000
_diffrn_orient_matrix_UB_31      0.1854236000
_diffrn_orient_matrix_UB_32      0.0037529000
_diffrn_orient_matrix_UB_33      -0.0058882000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            43178
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.583
_diffrn_reflns_theta_min         2.961
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.116
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.701
_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    1.291
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0017(3)
_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   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         6442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0547P)^2^+0.7011P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1083
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5831
_reflns_number_total             6442
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00268g3.cif
_cod_data_source_block           rja230012_fa
_cod_depositor_comments
'Adding full bibliography for 7132810--7132818.cif.'
_cod_database_code               7132810
_chemical_oxdiff_formula         'C18 H20 Cl1 N1 O2'
_shelx_estimated_absorpt_t_max   0.902
_shelx_estimated_absorpt_t_min   0.599
_diffrn_oxdiff_digest_frames
;
01c2c86d7b77daaf35a4fa164a9d555191071369aa8
;
_diffrn_oxdiff_digest_hkl
;
011763e7b29138f8e8fcfb12b4ceda38baa0ca
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C21(H21), C22(H22), C24(H24), C25(H25), C29(H29), C30(H30), C31(H31), C32(H32)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C26(H26A,H26B,H26C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,
 H36B,H36C)
;
_shelx_res_checksum              28160
_shelx_hkl_checksum              49209
_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 1.354
_oxdiff_exptl_absorpt_empirical_full_min 0.723