Axially-chiral boramidine for detailed (chir)optical studies.
Saleh, Nidal; Sucre-Rosales, Estefanía; Zinna, Francesco; Besnard, Céline; Vauthey, Eric; Lacour, Jérôme; Chemical science 15 (2024) 6530–6535; doi:10.1039/d4sc00870g

data_1571335
_publ_section_title
;
 Axially-chiral boramidine for detailed (chir)optical studies.
;
_journal_issue                   17
_journal_name_full               'Chemical science'
_journal_page_first              6530
_journal_page_last               6535
_journal_paper_doi               10.1039/d4sc00870g
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H16 N2'
_chemical_formula_sum            'C17 H16 N2'
_chemical_formula_weight         248.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-29
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-12-21 deposited with the CCDC.	2024-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.8699(2)
_cell_length_b                   14.53966(15)
_cell_length_c                   7.44906(8)
_cell_measurement_reflns_used    50782
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      73.5160
_cell_measurement_theta_min      3.3990
_cell_volume                     2801.89(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_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    -55.00 -18.00   0.50    6.00    --  -52.73   0.00 -60.00   74
  2  \w    -88.00 -24.00   0.50    6.00    --  -52.73   0.00-150.00  128
  3  \w    -76.00 -47.00   0.50    6.00    --  -52.73 125.00  30.00   58
  4  \w    -82.00 -22.00   0.50    6.00    --  -52.73 -15.00  90.00  120
  5  \w    -70.00 -38.00   0.50    6.00    --  -52.73 125.00  60.00   64
  6  \w    -78.00 -37.00   0.50    6.00    --  -52.73 125.00-180.00   82
  7  \w    -62.00 -36.00   0.50    6.00    --  -52.73 125.00  90.00   52
  8  \w     34.00  74.00   0.50    6.00    --   66.46 -94.00 -90.00   80
  9  \w     34.00  63.00   0.50    6.00    --   66.46 -94.00 120.00   58
 10  \w     38.00  66.00   0.50    6.00    --   66.46-125.00   0.00   56
 11  \w     37.00  73.00   0.50    6.00    --   66.46 -94.00  60.00   72
 12  \w     34.00  60.00   0.50    6.00    --   66.46 -94.00-180.00   52
 13  \w     29.00  70.00   0.50    6.00    --   66.46 -94.00   0.00   82
 14  \w     77.00 111.00   0.50    6.00    --   66.46  15.00 -30.00   68
 15  \w     42.00  68.00   0.50    6.00    --   66.46  15.00 -30.00   52
 16  \w     75.00 113.00   0.50    6.00    --   66.46  26.00  -5.00   76
 17  \w     29.00  55.00   0.50    6.00    --   66.46 -94.00  30.00   52
 18  \w     31.00  69.00   0.50    6.00    --   66.46 -94.00-150.00   76
 19  \w     68.00  93.00   0.50    6.00    --   66.46-125.00  90.00   50
 20  \w     71.00  97.00   0.50    6.00    --   69.88-125.00 150.00   52
 21  \w     41.00  68.00   0.50    6.00    --   69.88 -94.00 150.00   54
 22  \w     49.00  96.00   0.50    6.00    --   69.88  15.00-150.00   94
 23  \w     42.00  96.00   0.50    6.00    --   69.88-125.00 120.00  108
 24  \w     85.00 110.00   0.50    6.00    --   69.88  15.00 150.00   50
 25  \w     68.00  95.00   0.50    6.00    --   69.88   0.00-120.00   54
 26  \w     74.00  99.00   0.50    6.00    --   69.88-132.00 145.00   50
 27  \w     71.00 111.00   0.50    6.00    --   69.88  15.00 120.00   80
 28  \w     40.00  65.00   0.50    6.00    --   69.88  15.00 120.00   50
 29  \w     51.00  76.00   0.50    6.00    --   69.88  15.00 150.00   50
 30  \w      9.00  34.00   0.50    6.00    --    4.00  30.00 145.61   50
 31  \w      4.00  30.00   0.50    6.00    --   -4.00  33.00-152.91   52
 32  \w     12.00  39.00   0.50    6.00    --    8.00  29.00-149.92   54
 33  \w      1.00  27.00   0.50    6.00    --   -8.00  35.00  66.01   52
 34  \w      1.00  26.00   0.50    6.00    --   -8.00  35.00-108.57   50
 35  \w     11.00  37.00   0.50    6.00    --    8.00  29.00 119.23   52
 36  \w     14.00  40.00   0.50    6.00    --   12.00  28.00 -86.04   52
 37  \w     14.00  40.00   0.50    6.00    --   12.00  28.00 -15.15   52
 38  \w     -2.00  25.00   0.50    6.00    --  -12.00  36.00 -50.62   54
 39  \w     20.00  48.00   0.50    6.00    --   20.00  26.00  22.21   56
 40  \w     21.00  48.00   0.50    6.00    --   20.00  26.00  65.56   54
 41  \w     25.00  51.00   0.50    6.00    --   20.00  25.00-136.04   52
 42  \w    -12.00  13.00   0.50    6.00    --  -24.00  44.00   2.51   50
 43  \w    -51.00 -26.00   0.50    6.00    --  -32.00 -25.00 -48.28   50
 44  \w    -51.00 -26.00   0.50    6.00    --  -32.00 -25.00  13.94   50
 45  \w    -29.00  -3.00   0.50    6.00    --  -40.00  67.00  65.87   52
 46  \w     32.00  60.00   0.50    6.00    --   40.00  23.00 -86.02   56
 47  \w     34.00  59.00   0.50    6.00    --   48.00  23.00   0.75   50
 48  \w    -62.00 -37.00   0.50    6.00    --  -48.00 -23.00 -59.25   50
 49  \w    -62.00 -36.00   0.50    6.00    --  -48.00 -23.00-134.31   52
 50  \w    -78.00 -15.00   0.50    6.00    --  -52.73   0.00   0.00  126
 51  \w    -90.00 -37.00   0.50    6.00    --  -52.73   0.00 -90.00  106
 52  \w     41.00  69.00   0.50    6.00    --   56.00  22.00 -68.76   56
 53  \w     43.00  71.00   0.50    6.00    --   56.00  22.00  54.40   56
 54  \w    -70.00 -45.00   0.50    6.00    --  -60.00 -22.00  60.62   50
 55  \w    -70.00 -45.00   0.50    6.00    --  -60.00 -22.00  76.43   50
 56  \w    -71.00 -45.00   0.50    6.00    --  -60.50 -22.00   5.65   52
 57  \w    -50.00 -19.00   0.50    6.00    --  -60.50  61.00 -26.59   62
 58  \w    -49.00 -23.00   0.50    6.00    --  -60.50  45.00  47.63   52
 59  \w    -48.00 -22.00   0.50    6.00    --  -60.50  62.00  -4.04   52
 60  \w    -71.00 -45.00   0.50    6.00    --  -60.50 -22.00 179.33   52
 61  \w    -71.00 -46.00   0.50    6.00    --  -60.50 -22.00  -9.88   50
 62  \w    -48.00 -23.00   0.50    6.00    --  -60.50  66.00  98.25   50
 63  \w    -39.00 -14.00   0.50    6.00    --  -60.50  37.00  74.04   50
 64  \w     35.00  60.00   0.50    6.00    --   66.46-125.00 -90.00   50
 65  \w     67.00  93.00   0.50    6.00    --   66.46-125.00 -90.00   52
 66  \w     35.00  91.00   0.50    6.00    --   66.46-125.00 -30.00  112
 67  \w     38.00  64.00   0.50    6.00    --   66.46-125.00 120.00   52
 68  \w     68.00  93.00   0.50    6.00    --   66.46-125.00 150.00   50
 69  \w     35.00  61.00   0.50    6.00    --   66.46-125.00 150.00   52
 70  \w     35.00  61.00   0.50    6.00    --   69.88-125.00   0.00   52
 71  \w     33.00  62.00   0.50    6.00    --   69.88   0.00 -60.00   58
 72  \w     40.00  95.00   0.50    6.00    --   69.88   0.00 150.00  110
 73  \w     40.00  99.00   0.50    6.00    --   69.88   0.00  90.00  118
 74  \w     72.00  97.00   0.50    6.00    --   69.88-125.00   0.00   50
 75  \w     36.00  92.00   0.50    6.00    --   69.88   0.00  30.00  112
 76  \w     56.00  98.00   0.50    6.00    --   69.88   0.00 -30.00   84
 77  \w     39.00 100.00   0.50    6.00    --   69.88   0.00-150.00  122
 78  \w     72.00  97.00   0.50    6.00    --   69.88-125.00 -60.00   50
 79  \w     36.00  62.00   0.50    6.00    --   69.88-125.00 -60.00   52
 80  \w     69.00  95.00   0.50    6.00    --   69.88-125.00-150.00   52
 81  \w     35.00  61.00   0.50    6.00    --   69.88-125.00-150.00   52
 82  \w     65.00  90.00   0.50    6.00    --   69.88   0.00 -60.00   50
 83  \w     64.00 100.00   0.50    6.00    --   75.27-120.00  56.72   72
 84  \w     36.00  61.00   0.50    6.00    --   75.27-120.00  56.72   50
 85  \w     70.00 105.00   0.50    6.00    --   75.27-131.00-168.92   70
 86  \w     42.00  68.00   0.50    6.00    --   75.27-131.00-168.92   52
 87  \w     59.00 112.00   0.50    6.00    --   75.27  21.00  74.82  106
 88  \w     76.00 106.00   0.50    6.00    --   75.27-131.00  95.96   60
 89  \w     39.00  64.00   0.50    6.00    --   75.27-131.00  95.96   50
 90  \w     94.00 119.00   0.50    6.00    --   75.27  21.00 113.72   50
 91  \w     57.00  83.00   0.50    6.00    --   75.27  21.00 113.72   52
 92  \w     58.00 111.00   0.50    6.00    --   75.27  21.00-126.54  106
 93  \w     89.00 120.00   0.50    6.00    --   75.27  20.00-153.78   62
 94  \w     54.00  83.00   0.50    6.00    --   75.27  20.00-153.78   58
 95  \w     58.00  83.00   0.50    6.00    --   75.27  21.00  57.80   50
 96  \w     69.00 101.00   0.50    6.00    --   75.27  21.00  27.83   64
 97  \w     70.00  96.00   0.50    6.00    --   75.27-114.00 -89.35   52
 98  \w     37.00  98.00   0.50    6.00    --   75.27-118.00 -17.85  122
 99  \w     36.00  63.00   0.50    6.00    --   75.27-114.00 -89.35   54
100  \w     65.00  96.00   0.50    6.00    --   75.27  21.00 -40.79   62
101  \w     86.00 120.00   0.50    6.00    --   75.27  21.00-114.62   68
102  \w     57.00  83.00   0.50    6.00    --   75.27  20.00 178.08   52
103  \w     76.00 101.00   0.50    6.00    --   75.27-123.00-140.91   50
104  \w     60.00  85.00   0.50    6.00    --   75.27  21.00-114.62   50
105  \w     57.00  95.00   0.50    6.00    --   75.27  21.00   2.58   76
106  \w     50.00 101.00   0.50    6.00    --   75.27  19.00 -60.70  102
107  \w     34.00  60.00   0.50    6.00    --   75.27-123.00-140.91   52
108  \w     94.00 120.00   0.50    6.00    --   75.27  21.00 130.01   52
109  \w     54.00 104.00   0.50    6.00    --   75.27  20.00 -53.29  100
110  \w     60.00  85.00   0.50    6.00    --   75.27  21.00 130.01   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0001445000
_diffrn_orient_matrix_UB_12      0.0018664000
_diffrn_orient_matrix_UB_13      -0.2067417000
_diffrn_orient_matrix_UB_21      0.0557637000
_diffrn_orient_matrix_UB_22      -0.0372640000
_diffrn_orient_matrix_UB_23      -0.0008131000
_diffrn_orient_matrix_UB_31      -0.0209133000
_diffrn_orient_matrix_UB_32      -0.0991780000
_diffrn_orient_matrix_UB_33      -0.0036780000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            85307
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.875
_diffrn_reflns_theta_min         3.417
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.538
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
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    1.177
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 2246 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 The resonant scattering is weak for this sample (Friedif 12) 
 as reflected by the large error of the refined Flack parameter (-0.1(4)). 
 However, all indicators confirm the absolute structure (Hooft -0.05(6) 
 with P3(true)=1 and the post refinement Parsons-Flack 
 x determined using 2246 quotients is -0.03(7)  
;
_refine_ls_abs_structure_Flack   -0.03(7)
_refine_ls_extinction_coef       0.00139(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         5555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0292
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0396P)^2^+0.4160P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0759
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                5436
_reflns_number_total             5555
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc00870g2.cif
_cod_data_source_block           nid_enantio
_cod_depositor_comments          'Adding full bibliography for 1571335.cif.'
_cod_database_code               1571335
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'C17 H16 N2'
_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:
 C4(H4), C5(H5), C13(H13), C18(H18), C5B(H5B), C16(H16), C17(H17), C4B(H4B),
 C18B(H18B), C12B(H12B), C15(H15), C13B(H13B), C15B(H15B), C12(H12), C17B(H17B),
  C16B(H16B)
2.b Idealised Me refined as rotating group:
 C11(H11D,H11E,H11F), C7B(H7BA,H7BB,H7BC), C7(H7A,H7B,H7C), C11B(H11A,H11B,H11C)
;
_shelx_res_checksum              38258
_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 2.015
_oxdiff_exptl_absorpt_empirical_full_min 0.497