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_7132818
_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         'C13 H18 Cl N O'
_chemical_formula_sum            'C13 H18 Cl N O'
_chemical_formula_weight         239.746
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-01-25
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-11-13 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                93.580(2)
_cell_angle_beta                 96.362(2)
_cell_angle_gamma                93.083(2)
_cell_formula_units_Z            2
_cell_length_a                   6.66649(19)
_cell_length_b                   9.4285(3)
_cell_length_c                   10.2117(3)
_cell_measurement_reflns_used    7636
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      75.8840
_cell_measurement_theta_min      4.3590
_cell_volume                     635.47(3)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_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 0.9987
_diffrn_measured_fraction_theta_max 0.9295
_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  90.00   0.50    0.05    --   48.76 156.00 -20.00   64
  2  \w      0.00  25.00   0.50    0.05    --   38.00  97.00  91.24   50
  3  \w    -44.00 -14.00   0.50    0.05    --   10.00 128.00  93.35   60
  4  \w    -33.00  -8.00   0.50    0.05    --   14.00 116.00  24.95   50
  5  \w     15.00  40.00   0.50    0.05    --   50.00  91.00 118.39   50
  6  \w     15.00  40.00   0.50    0.05    --   50.00  92.00  57.26   50
  7  \w    -26.00  -1.00   0.50    0.05    --   18.00 108.00-135.02   50
  8  \w      8.00  37.00   0.50    0.05    --   42.00  90.00-100.38   58
  9  \w     16.00  41.00   0.50    0.05    --   50.00  90.00-114.30   50
 10  \w     24.00  90.00   0.50    0.05    --   48.76  77.00   0.00  132
 11  \w     44.00  69.00   0.50    0.05    --   70.00  76.00-108.70   50
 12  \w     70.00 113.00   0.50    0.05    --   96.11  77.00  30.00   86
 13  \w     33.00  60.00   0.50    0.05    --   58.00  76.00  91.53   54
 14  \w     33.00  59.00   0.50    0.05    --   58.00  75.00 147.44   52
 15  \w     32.00  70.00   0.50    0.05    --   54.00  77.00 174.11   76
 16  \w     87.00 112.00   0.50    0.05    --   54.00  77.00 174.11   50
 17  \w     82.00 107.00   0.50    0.05    --   96.11 156.00 -20.00   50
 18  \w    103.00 128.00   0.50    0.05    --  108.00 120.00-176.00   50
 19  \w     21.00  49.00   0.50    0.05    --   96.11 -45.00-180.00   56
 20  \w     35.00  67.00   0.50    0.05    --  108.00 -61.00-120.00   64
 21  \w     19.00  51.00   0.50    0.05    --   96.11 -45.00 -30.00   64
 22  \w     34.00  69.00   0.50    0.05    --  108.00 -61.00 120.00   70
 23  \w     39.00 106.00   0.50    0.05    --  108.00 -95.00 120.00  134
 24  \w     70.00 109.00   0.50    0.05    --  108.00-120.00  99.00   78
 25  \w     28.00 105.00   0.50    0.05    --   96.11 -95.00 -30.00  154
 26  \w     43.00  95.00   0.50    0.05    --  108.00 -95.00 -90.00  104
 27  \w     62.00  87.00   0.50    0.05    --  108.00-156.00 -57.00   50
 28  \w     57.00  82.00   0.50    0.05    --   96.11-156.00 -57.00   50
 29  \w     53.00  78.00   0.50    0.05    --   48.76-156.00 -57.00   50
 30  \w     50.00  96.00   0.50    0.05    --   48.76-120.00  99.00   92
 31  \w     17.00  47.00   0.50    0.05    --   48.76-120.00  99.00   60
 32  \w   -130.00-105.00   0.50    0.05    --  -92.01-156.00 -57.00   50
 33  \w    -83.00 -53.00   0.50    0.05    --  -49.76-156.00 -57.00   60
 34  \w   -121.00 -96.00   0.50    0.05    --  -92.01-120.00  99.00   50
 35  \w   -152.00-126.00   0.50    0.05    --  -92.01 -61.00   0.00   52
 36  \w    -93.00 -65.00   0.50    0.05    --  -92.01 -77.00-150.00   56
 37  \w    -53.00 -26.00   0.50    0.05    --  -49.76 -77.00-120.00   54
 38  \w    -49.00 -23.00   0.50    0.05    --  -49.76 -77.00 -60.00   52
 39  \w   -146.00-103.00   0.50    0.05    --  -92.01 -77.00-150.00   86
 40  \w   -109.00 -68.00   0.50    0.05    --  -92.01 -77.00 -90.00   82
 41  \w   -141.00 -70.00   0.50    0.05    --  -92.01 -77.00  90.00  142
 42  \w   -156.00 -65.00   0.50    0.05    --  -92.01 -77.00 120.00  182
 43  \w    -60.00 -35.00   0.50    0.05    --  -62.00 -77.00 154.17   50
 44  \w    -73.00 -48.00   0.50    0.05    --  -74.00 -76.00 118.28   50
 45  \w   -114.00 -88.00   0.50    0.05    --  -62.00 -77.00 154.17   52
 46  \w    -69.00 -44.00   0.50    0.05    --  -70.00 -76.00  33.99   50
 47  \w    -89.00 -53.00   0.50    0.05    --  -78.00 -76.00 -44.95   72
 48  \w    -74.00 -48.00   0.50    0.05    --  -74.00 -76.00 -87.50   52
 49  \w   -145.00 -99.00   0.50    0.05    --  -78.00 -76.00 -44.95   92
 50  \w   -148.00-112.00   0.50    0.05    --  -92.01 -77.00 -90.00   72
 51  \w    -70.00 -45.00   0.50    0.05    --  -70.00 -74.00-176.61   50
 52  \w    -63.00 -37.00   0.50    0.05    --  -62.00 -73.00 -92.56   52
 53  \w    -79.00 -52.00   0.50    0.05    --  -78.00 -75.00  13.71   54
 54  \w   -100.00 -65.00   0.50    0.05    --  -90.00 -73.00 -45.61   70
 55  \w   -145.00-106.00   0.50    0.05    --  -78.00 -75.00  13.71   78
 56  \w   -158.00-118.00   0.50    0.05    --  -90.00 -73.00 -45.61   80
 57  \w   -163.00-137.00   0.50    0.05    --  -99.00 -73.00-155.54   52
 58  \w   -102.00 -74.00   0.50    0.05    --  -99.00 -73.00-155.54   56
 59  \w    -73.00 -47.00   0.50    0.05    --  -70.00 -72.00 -31.01   52
 60  \w   -113.00 -75.00   0.50    0.05    --  -99.00 -71.00 -72.31   76
 61  \w   -154.00-116.00   0.50    0.05    --  -90.00 -71.00 -25.17   76
 62  \w   -166.00-126.00   0.50    0.05    --  -99.00 -71.00 -72.31   80
 63  \w   -103.00 -66.00   0.50    0.05    --  -90.00 -71.00 -25.17   74
 64  \w   -145.00 -76.00   0.50    0.05    --  -99.00 -70.00-131.59  138
 65  \w    -96.00 -54.00   0.50    0.05    --  -78.00 -71.00  59.40   84
 66  \w    -88.00 -55.00   0.50    0.05    --  -78.00 -69.00  71.80   66
 67  \w    -93.00 -57.00   0.50    0.05    --  -78.00 -70.00  99.66   72
 68  \w    -95.00 -66.00   0.50    0.05    --  -90.00 -71.00 132.93   58
 69  \w    -77.00 -51.00   0.50    0.05    --  -74.00 -69.00 167.34   52
 70  \w   -161.00 -69.00   0.50    0.05    --  -90.00 -67.00 168.96  184
 71  \w   -158.00 -64.00   0.50    0.05    --  -86.00 -69.00  31.60  188
 72  \w    -94.00 -65.00   0.50    0.05    --  -86.00 -63.00 139.73   58
 73  \w   -156.00-112.00   0.50    0.05    --  -86.00 -63.00 139.73   88
 74  \w    -92.00 -67.00   0.50    0.05    --  -90.00 -69.00  48.86   50
 75  \w    -94.00 -69.00   0.50    0.05    --  -90.00 -66.00 -11.62   50
 76  \w    -98.00 -73.00   0.50    0.05    --  -92.01 -61.00   0.00   50
 77  \w    -88.00 -62.00   0.50    0.05    --  -82.00 -66.00-128.43   52
 78  \w   -100.00 -67.00   0.50    0.05    --  -92.01  77.00-180.00   66
 79  \w    -63.00 -36.00   0.50    0.05    --  -92.01  77.00-180.00   54
 80  \w   -100.00 -50.00   0.50    0.05    --  -92.01 120.00-176.00  100
 81  \w    -68.00 -42.00   0.50    0.05    --  -49.76 120.00-176.00   52
 82  \w    -89.00 -64.00   0.50    0.05    --  -92.01 156.00 -20.00   50
 83  \w    -62.00 -24.00   0.50    0.05    --  -92.01  77.00  30.00   76
;
_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      0.1383649000
_diffrn_orient_matrix_UB_12      -0.0496893000
_diffrn_orient_matrix_UB_13      0.1171478000
_diffrn_orient_matrix_UB_21      0.1490456000
_diffrn_orient_matrix_UB_22      -0.0508641000
_diffrn_orient_matrix_UB_23      -0.0953809000
_diffrn_orient_matrix_UB_31      0.1136246000
_diffrn_orient_matrix_UB_32      0.1478062000
_diffrn_orient_matrix_UB_33      0.0181983000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.9987
_diffrn_reflns_Laue_measured_fraction_max 0.9295
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13900
_diffrn_reflns_point_group_measured_fraction_full 0.9987
_diffrn_reflns_point_group_measured_fraction_max 0.9295
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         77.60
_diffrn_reflns_theta_min         4.37
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.486
_exptl_absorpt_correction_T_max  0.873
_exptl_absorpt_correction_T_min  0.667
_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    1.253
_exptl_crystal_description       block
_exptl_crystal_F_000             257.434
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.2271
_refine_diff_density_min         -0.2115
_refine_diff_density_rms         0.0370
_refine_ls_d_res_high            0.7893
_refine_ls_d_res_low             10.1247
_refine_ls_extinction_coef       0.0044(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0393
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2505
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0393
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0304
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0397P)^2^+0.1645P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0812
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2334
_reflns_number_total             2505
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4cc00268g3.cif
_cod_data_source_block           rja230008_fa
_cod_depositor_comments
'Adding full bibliography for 7132810--7132818.cif.'
_cod_database_code               7132818
_chemical_oxdiff_formula         'C13 H18 Cl1 N1 O1'
_diffrn_oxdiff_digest_frames
;
0100b4ee7ff8f213440eb12b4ed1310cce05902c7be
;
_diffrn_oxdiff_digest_hkl
;
01de8c1636134dc45f8b1aeeae182e5593917a
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C3(H3a,H3b,H3c), C11(H11a,H11b,H11c), C13(H13a,H13b,H13c)
;
_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 1.572
_oxdiff_exptl_absorpt_empirical_full_min 0.671