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_7132817
_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_absolute_configuration ad
_chemical_formula_moiety         'C17 H18 Cl N O'
_chemical_formula_sum            'C17 H18 Cl N O'
_chemical_formula_weight         287.77
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-28
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.63450(10)
_cell_length_b                   9.62950(10)
_cell_length_c                   20.4737(2)
_cell_measurement_reflns_used    12444
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      78.2760
_cell_measurement_theta_min      2.1840
_cell_volume                     1505.15(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 1.3 (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 0.957
_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    -36.00  22.00   0.50    0.10    --  -49.76  57.00-180.00  116
  2  \w    -42.00  -5.00   0.50    0.10    --  -49.76  38.00 -30.00   74
  3  \w     -2.00  29.00   0.50    0.10    --  -49.76  38.00 -30.00   62
  4  \w    -27.00  19.00   0.50    0.10    --  -49.76  19.00  60.00   92
  5  \w     74.00 100.00   0.50    0.10    --   48.76 125.00 -60.00   52
  6  \w     71.00  96.00   0.50    0.10    --   48.76 129.00 -36.00   50
  7  \w     96.00 121.00   0.50    0.10    --   96.11 129.00 -36.00   50
  8  \w     73.00  98.00   0.50    0.10    --   48.76 141.00 135.00   50
  9  \w    116.00 141.00   0.50    0.10    --   96.11 141.00 135.00   50
 10  \w     94.00 119.00   0.50    0.10    --  108.00 141.00 135.00   50
 11  \w    -30.00  19.00   0.50    0.10    --   48.76 -19.00 120.00   98
 12  \w     19.00  44.00   0.50    0.10    --   96.11 -45.00  30.00   50
 13  \w     43.00  88.00   0.50    0.10    --  108.00 -77.00  60.00   90
 14  \w     51.00  95.00   0.50    0.10    --   96.11 -77.00 -60.00   88
 15  \w     79.00 104.00   0.50    0.10    --  108.00 -77.00-120.00   50
 16  \w     20.00  48.00   0.50    0.10    --   96.11 -45.00-150.00   56
 17  \w     22.00  49.00   0.50    0.10    --   96.11 -45.00 -90.00   54
 18  \w    -27.00  23.00   0.50    0.10    --   48.76 -19.00  60.00  100
 19  \w     66.00 106.00   0.50    0.10    --  108.00 -95.00 120.00   80
 20  \w     43.00  75.00   0.50    0.10    --   96.11-141.00  78.00   64
 21  \w     59.00 124.00   0.50    0.10    --  108.00-141.00  78.00  130
 22  \w     57.00  84.00   0.50    0.10    --   48.76-141.00  78.00   54
 23  \w     36.00 109.00   0.50    0.10    --  108.00-125.00 -60.00  146
 24  \w     51.00  76.00   0.50    0.10    --  108.00-129.00-109.00   50
 25  \w     45.00  70.00   0.50    0.10    --   96.11-129.00-109.00   50
 26  \w     37.00  62.00   0.50    0.10    --   48.76-129.00-109.00   50
 27  \w   -111.00 -77.00   0.50    0.10    --  -92.01 125.00  90.00   68
 28  \w   -123.00 -21.00   0.50    0.10    --  -92.01 141.00 135.00  204
 29  \w    -76.00 -51.00   0.50    0.10    --  -49.76 141.00 135.00   50
 30  \w    -85.00 -60.00   0.50    0.10    --  -49.76 129.00 -36.00   50
 31  \w    -91.00 -66.00   0.50    0.10    --  -92.01 129.00 -36.00   50
 32  \w    -71.00 -24.00   0.50    0.10    --  -92.01  61.00 -60.00   94
 33  \w    -51.00 -14.00   0.50    0.10    --  -92.01  45.00-180.00   74
 34  \w    -49.00 -14.00   0.50    0.10    --  -92.01  45.00   0.00   70
 35  \w    -48.00 -17.00   0.50    0.10    --  -92.01  45.00  90.00   62
 36  \w    -67.00 -17.00   0.50    0.10    --  -92.01  61.00 120.00  100
 37  \w    -50.00 -16.00   0.50    0.10    --  -92.01  45.00 120.00   68
 38  \w   -167.00 -73.00   0.50    0.10    --  -92.01 -30.00  60.00  188
 39  \w   -138.00-113.00   0.50    0.10    --  -92.01-141.00  78.00   50
 40  \w   -116.00 -77.00   0.50    0.10    --  -49.76-125.00 120.00   78
 41  \w   -132.00-107.00   0.50    0.10    --  -92.01 -95.00 120.00   50
 42  \w   -161.00 -75.00   0.50    0.10    --  -92.01-125.00  30.00  172
 43  \w   -129.00 -84.00   0.50    0.10    --  -92.01 -95.00 -60.00   90
 44  \w   -129.00 -86.00   0.50    0.10    --  -92.01-129.00-109.00   86
 45  \w   -121.00 -96.00   0.50    0.10    --  -49.76-129.00-109.00   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      0.1295545000
_diffrn_orient_matrix_UB_12      0.1137524000
_diffrn_orient_matrix_UB_13      0.0215856000
_diffrn_orient_matrix_UB_21      0.0457156000
_diffrn_orient_matrix_UB_22      0.0289651000
_diffrn_orient_matrix_UB_23      -0.0720173000
_diffrn_orient_matrix_UB_31      -0.1477550000
_diffrn_orient_matrix_UB_32      0.1087015000
_diffrn_orient_matrix_UB_33      -0.0033833000
_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  0.0346
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19192
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.455
_diffrn_reflns_theta_min         4.319
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.194
_exptl_absorpt_correction_T_max  0.855
_exptl_absorpt_correction_T_min  0.740
_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    1.270
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1201 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(5)
_refine_ls_extinction_coef       0.0025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3057
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0252
_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^)+(0.0362P)^2^+0.1814P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0649
_refine_ls_wR_factor_ref         0.0654
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.926
_reflns_number_gt                2971
_reflns_number_total             3057
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00268g3.cif
_cod_data_source_block           rja220004_fa
_cod_depositor_comments
'Adding full bibliography for 7132810--7132818.cif.'
_cod_database_code               7132817
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C17 H18 Cl1 N1 O1'
_shelx_estimated_absorpt_t_max   0.844
_shelx_estimated_absorpt_t_min   0.644
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              49091
_shelx_hkl_checksum              54157
_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 1.306
_oxdiff_exptl_absorpt_empirical_full_min 0.780