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_7132816
_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         'C16 H22 Cl N O'
_chemical_formula_sum            'C16 H22 Cl N O'
_chemical_formula_weight         279.79
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-17
_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                 93.319(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6132(6)
_cell_length_b                   6.8258(4)
_cell_length_c                   17.3255(8)
_cell_measurement_reflns_used    8454
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      75.9530
_cell_measurement_theta_min      3.5010
_cell_volume                     1489.14(13)
_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  (Sheldrick, 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 0.999
_diffrn_measured_fraction_theta_max 0.934
_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     83.00 178.00   0.50    1.14    --  108.00 106.00  50.00  190
  2  \w     83.00 167.00   0.50    1.14    --   96.11 106.00  50.00  168
  3  \w     74.00 121.00   0.50    1.14    --   48.51 125.00-120.00   94
  4  \w     74.00 121.00   0.50    1.14    --   48.51 125.00-180.00   94
  5  \w     -2.00  92.00   0.50    1.14    --   48.51-106.00 -48.00  188
  6  \w     36.00 111.00   0.50    1.14    --  108.00-125.00 -90.00  150
  7  \w     25.00 107.00   0.50    1.14    --   96.11-106.00 -48.00  164
  8  \w     37.00 107.00   0.50    1.14    --  108.00-106.00 -48.00  140
  9  \w     40.00 105.00   0.50    1.14    --  108.00 -77.00   0.00  130
 10  \w     34.00  71.00   0.50    1.14    --  108.00 -61.00  90.00   74
 11  \w     18.00  51.00   0.50    1.14    --   96.11 -45.00  90.00   66
 12  \w     18.00  51.00   0.50    1.14    --   96.11 -45.00 120.00   66
 13  \w   -118.00 -23.00   0.50    1.14    --  -49.38 -77.00  30.00  190
 14  \w   -163.00 -83.00   0.50    1.14    --  -92.01-106.00 -48.00  160
 15  \w   -118.00 -44.00   0.50    1.14    --  -49.38 -77.00 -90.00  148
 16  \w   -118.00 -23.00   0.50    1.14    --  -49.38 -77.00 150.00  190
 17  \w    -92.00   2.00   0.50    1.14    --  -49.38 106.00  50.00  188
 18  \w   -107.00 -21.00   0.50    1.14    --  -92.01 106.00  50.00  172
 19  \w    -51.00 -14.00   0.50    1.14    --  -92.01  45.00  30.00   74
 20  \w    -51.00 -14.00   0.50    1.14    --  -92.01  45.00  60.00   74
 21  \w    -51.00 -14.00   0.50    1.14    --  -92.01  45.00   0.00   74
 22  \w    -51.00 -14.00   0.50    1.14    --  -92.01  45.00 -30.00   74
 23  \w    -51.00 -14.00   0.50    1.14    --  -92.01  45.00 -90.00   74
 24  \w    -51.00 -14.00   0.50    1.14    --  -92.01  45.00-150.00   74
;
_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      0.0314038000
_diffrn_orient_matrix_UB_12      -0.2183094000
_diffrn_orient_matrix_UB_13      -0.0004598000
_diffrn_orient_matrix_UB_21      -0.0193117000
_diffrn_orient_matrix_UB_22      -0.0048487000
_diffrn_orient_matrix_UB_23      -0.0885527000
_diffrn_orient_matrix_UB_31      0.1165503000
_diffrn_orient_matrix_UB_32      0.0581875000
_diffrn_orient_matrix_UB_33      -0.0090890000
_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  0.0307
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13974
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.217
_diffrn_reflns_theta_min         3.510
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.195
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.743
_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    1.248
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0633P)^2^+0.8209P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1337
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2426
_reflns_number_total             2982
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00268g3.cif
_cod_data_source_block           rja230006_2_fa
_cod_depositor_comments
'Adding full bibliography for 7132810--7132818.cif.'
_cod_original_cell_volume        1489.13(14)
_cod_database_code               7132816
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C16 H21 Cl1 N1 O1'
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.656
_reflns_odcompleteness_completeness 99.90
_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), C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              86978
_shelx_hkl_checksum              43813
_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 1.259
_oxdiff_exptl_absorpt_empirical_full_min 0.752