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_7132813
_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         'C14 H18 Cl N O'
_chemical_formula_sum            'C14 H18 Cl N O'
_chemical_formula_weight         251.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.12.01 svn.r5f60950 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-11-13 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.817(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.5653(4)
_cell_length_b                   6.36990(10)
_cell_length_c                   23.6434(5)
_cell_measurement_reflns_used    6863
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      77.1680
_cell_measurement_theta_min      3.9400
_cell_volume                     2646.61(10)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.943
_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    -40.00 -15.00   0.50    0.15    --  -92.01  45.00 120.00   50
  2  \w    -45.00 -19.00   0.50    0.15    --  -92.01  45.00  90.00   52
  3  \w    -65.00 -17.00   0.50    0.15    --  -92.01  61.00  30.00   96
  4  \w    -41.00 -14.00   0.50    0.15    --  -92.01  37.00 -58.00   54
  5  \w    -70.00 -17.00   0.50    0.15    --  -92.01  61.00-120.00  106
  6  \w    -31.00  -6.00   0.50    0.15    --  -49.76  37.00 -58.00   50
  7  \w    -25.00  13.00   0.50    0.15    --  -49.76  19.00 -90.00   76
  8  \w    -24.00  28.00   0.50    0.15    --  -49.76  19.00 -60.00  104
  9  \w    -23.00   5.00   0.50    0.15    --   48.76 -37.00 146.00   56
 10  \w     17.00  42.00   0.50    0.15    --   50.00  89.00 141.14   50
 11  \w     75.00 121.00   0.50    0.15    --   48.76 125.00-180.00   92
 12  \w    110.00 135.00   0.50    0.15    --  108.00  37.00 -58.00   50
 13  \w     72.00 150.00   0.50    0.15    --   96.11  77.00   0.00  156
 14  \w     79.00 155.00   0.50    0.15    --   96.11  77.00  30.00  152
 15  \w     87.00 165.00   0.50    0.15    --   96.11  77.00  90.00  156
 16  \w     71.00 110.00   0.50    0.15    --   96.11  77.00  60.00   78
 17  \w     50.00  85.00   0.50    0.15    --   48.76  37.00 -58.00   70
 18  \w     88.00 119.00   0.50    0.15    --   48.76  37.00 -58.00   62
 19  \w    120.00 145.00   0.50    0.15    --   96.11  37.00 -58.00   50
 20  \w     47.00  73.00   0.50    0.15    --  108.00 -77.00-180.00   52
 21  \w     34.00  70.00   0.50    0.15    --  108.00 -61.00 -90.00   72
 22  \w     46.00  71.00   0.50    0.15    --  108.00 -61.00   0.00   50
 23  \w     47.00  80.00   0.50    0.15    --  108.00 -77.00  60.00   66
 24  \w     40.00  89.00   0.50    0.15    --  108.00 -77.00 120.00   98
 25  \w    -81.00 -52.00   0.50    0.15    --  -49.76 -37.00 146.00   58
 26  \w    -90.00 -23.00   0.50    0.15    --  -49.76 -77.00  60.00  134
 27  \w    -45.00 -19.00   0.50    0.15    --  -92.01 125.00-150.00   52
 28  \w   -108.00 -54.00   0.50    0.15    --  -92.01 125.00-150.00  108
 29  \w    -91.00 -66.00   0.50    0.15    --  -92.01 -77.00  90.00   50
 30  \w    -89.00 -64.00   0.50    0.15    --  -86.00 -66.00  45.02   50
 31  \w    -99.00 -73.00   0.50    0.15    --  -92.01 -77.00  30.00   52
 32  \w    -86.00 -60.00   0.50    0.15    --  -82.00 -66.00  27.60   52
 33  \w   -156.00 -68.00   0.50    0.15    --  -92.01 -77.00   0.00  176
 34  \w   -148.00-123.00   0.50    0.15    --  -92.01 -77.00  30.00   50
 35  \w   -151.00 -60.00   0.50    0.15    --  -78.00 -61.00   0.81  182
 36  \w   -146.00 -75.00   0.50    0.15    --  -92.01 -45.00  60.00  142
 37  \w   -114.00 -75.00   0.50    0.15    --  -92.01 -37.00 146.00   78
;
_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      0.0404899000
_diffrn_orient_matrix_UB_12      0.0826326000
_diffrn_orient_matrix_UB_13      -0.0430851000
_diffrn_orient_matrix_UB_21      -0.0767443000
_diffrn_orient_matrix_UB_22      0.0783422000
_diffrn_orient_matrix_UB_23      -0.0427992000
_diffrn_orient_matrix_UB_31      0.0125212000
_diffrn_orient_matrix_UB_32      0.2134054000
_diffrn_orient_matrix_UB_33      0.0323809000
_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  0.0384
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14323
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.563
_diffrn_reflns_theta_min         3.950
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.414
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_T_min  0.671
_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    1.264
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.651
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0607
_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^)+(0.0702P)^2^+7.3674P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1564
_refine_ls_wR_factor_ref         0.1619
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2344
_reflns_number_total             2651
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00268g3.cif
_cod_data_source_block           rja230003_fa
_cod_depositor_comments
'Adding full bibliography for 7132810--7132818.cif.'
_cod_original_cell_volume        2646.61(9)
_cod_database_code               7132813
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H18 Cl1 N1 O1'
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.562
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              65873
_shelx_hkl_checksum              61884
_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 1.459
_oxdiff_exptl_absorpt_empirical_full_min 0.519