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_7132815
_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         'C15 H20 Cl N O'
_chemical_formula_sum            'C15 H20 Cl N O'
_chemical_formula_weight         265.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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                 92.075(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.0047(5)
_cell_length_b                   6.6560(2)
_cell_length_c                   24.7570(8)
_cell_measurement_reflns_used    5924
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      76.5020
_cell_measurement_theta_min      3.5680
_cell_volume                     2800.24(15)
_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 0.922
_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  15.00   0.50    0.05    --  -49.76  93.00 -82.00  174
  2  \w   -105.00 -24.00   0.50    0.05    --  -92.01  93.00 -82.00  162
  3  \w     -5.00  24.00   0.50    0.05    --  -49.76  19.00 -90.00   58
  4  \w     74.00 119.00   0.50    0.05    --   48.76 125.00-180.00   90
  5  \w     75.00 119.00   0.50    0.05    --   48.76 125.00 -60.00   88
  6  \w     83.00 140.00   0.50    0.05    --   96.11  93.00 -82.00  114
  7  \w     98.00 130.00   0.50    0.05    --  108.00  45.00 -90.00   64
  8  \w    143.00 169.00   0.50    0.05    --   96.11  61.00   0.00   52
  9  \w    109.00 144.00   0.50    0.05    --  108.00  77.00  30.00   70
 10  \w     92.00 131.00   0.50    0.05    --   96.11  61.00   0.00   78
 11  \w     19.00  51.00   0.50    0.05    --   96.11 -45.00 -60.00   64
 12  \w     21.00  51.00   0.50    0.05    --   96.11 -45.00-150.00   60
 13  \w     44.00  69.00   0.50    0.05    --  108.00 -61.00-180.00   50
 14  \w     34.00  60.00   0.50    0.05    --  108.00 -61.00-120.00   52
 15  \w     39.00  64.00   0.50    0.05    --  108.00 -61.00 -60.00   50
 16  \w     38.00  70.00   0.50    0.05    --  108.00 -61.00  60.00   64
 17  \w     27.00 108.00   0.50    0.05    --   96.11-125.00 150.00  162
 18  \w     28.00  63.00   0.50    0.05    --   96.11 -95.00  30.00   70
 19  \w     62.00  87.00   0.50    0.05    --  108.00 -93.00 165.00   50
 20  \w     29.00  98.00   0.50    0.05    --   96.11 -93.00 165.00  138
 21  \w     -9.00  66.00   0.50    0.05    --   48.76 -93.00 165.00  150
 22  \w   -120.00 -32.00   0.50    0.05    --  -49.76 -57.00   0.00  176
 23  \w   -160.00 -65.00   0.50    0.05    --  -92.01 -77.00-120.00  190
 24  \w   -160.00 -83.00   0.50    0.05    --  -92.01 -95.00  60.00  154
 25  \w   -153.00 -66.00   0.50    0.05    --  -92.01 -77.00 120.00  174
 26  \w   -133.00 -83.00   0.50    0.05    --  -92.01 -93.00 165.00  100
;
_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      0.0251893000
_diffrn_orient_matrix_UB_12      0.1612047000
_diffrn_orient_matrix_UB_13      0.0417860000
_diffrn_orient_matrix_UB_21      0.0244216000
_diffrn_orient_matrix_UB_22      0.1399175000
_diffrn_orient_matrix_UB_23      -0.0460762000
_diffrn_orient_matrix_UB_31      -0.0835409000
_diffrn_orient_matrix_UB_32      0.0895847000
_diffrn_orient_matrix_UB_33      -0.0032721000
_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  0.0331
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12518
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.220
_diffrn_reflns_theta_min         3.573
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.308
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0480P)^2^+1.3382P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0928
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2466
_reflns_number_total             2785
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00268g3.cif
_cod_data_source_block           rja230002_fa
_cod_depositor_comments
'Adding full bibliography for 7132810--7132818.cif.'
_cod_database_code               7132815
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H30 Cl1 N1 O1'
_shelx_estimated_absorpt_t_max   0.802
_shelx_estimated_absorpt_t_min   0.668
_reflns_odcompleteness_completeness 99.78
_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)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              21337
_shelx_hkl_checksum              41797
_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 1.224
_oxdiff_exptl_absorpt_empirical_full_min 0.865