One- and Two-Electron Reduction of Triarylborane-Based Helical Donor-Acceptor Compounds
Jia, Xiangqing; Nitsch, Jörn; Wu, Zhu; Friedrich, Alexandra; Krebs, Johannes; Krummenacher, Ivo; Fantuzzi, Felipe; Braunschweig, Holger; Moos, Michael; Lambert, Christoph; Engels, Bernd; Marder, Todd B.; Chemical Science  (2021) –; doi:10.1039/D1SC02409D

data_1564260
_publ_section_title
;
 One- and Two-Electron Reduction of Triarylborane-Based Helical
 Donor-Acceptor Compounds
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02409D
_journal_year                    2021
_chemical_formula_moiety         'C54 H48 B N, 1.5(C12 H24 K O6), C4 H8 O'
_chemical_formula_sum            'C76 H92 B K1.5 N O10'
_chemical_formula_weight         1248.96
_chemical_name_systematic
'1:1 13-(dimesitylboryl)-N,N-di-p-tolyldibenzo[c,g]phenanthren-8-amine (3-B(Mes)2-[5]helix-12-N(p-Tol)2) mono- and dianion'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-25
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.03.02 svn.r3394 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_audit_update_record
;
2020-11-13 deposited with the CCDC.	2021-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                87.406(3)
_cell_angle_beta                 72.123(3)
_cell_angle_gamma                67.804(3)
_cell_formula_units_Z            2
_cell_length_a                   13.5466(5)
_cell_length_b                   15.5380(6)
_cell_length_c                   18.5839(6)
_cell_measurement_reflns_used    24209
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.7610
_cell_measurement_theta_min      2.5120
_cell_volume                     3435.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -43.00 -17.00   0.50    4.01    --    6.00 129.00 -25.61   52
  2  \w    -35.00 -10.00   0.50    4.01    --   10.00 120.00 -38.94   50
  3  \w    -59.00 -33.00   0.50    4.01    --   10.00 160.00  88.17   52
  4  \w    -10.00  15.00   0.50    4.01    --   22.00  96.00  81.99   50
  5  \w      0.00  27.00   0.50    4.01    --   30.00  98.00  15.24   54
  6  \w      1.00  26.00   0.50    4.01    --   34.00  98.00-135.52   50
  7  \w     10.00  37.00   0.50    4.01    --   38.00  92.00-171.96   54
  8  \w      7.00  32.00   0.50    4.01    --   38.00  94.00  46.97   50
  9  \w     12.00  37.00   0.50    4.01    --   42.00  92.00 -99.66   50
 10  \w     17.00  42.00   0.50    4.01    --   46.00  90.00 -54.36   50
 11  \w     17.00  42.00   0.50    4.01    --   46.00  90.00  88.89   50
 12  \w     40.00  93.00   0.50    4.01    --   47.70-125.00  60.00  106
 13  \w     28.00  79.00   0.50    4.01    --   47.70-108.00 138.00  102
 14  \w    -84.00 -13.00   0.50    4.01    --  -47.70 125.00 -60.00  142
 15  \w    -81.00  -1.00   0.50    4.01    --  -47.70 108.00-123.00  160
 16  \w    -71.00 -35.00   0.50    4.01    --  -47.70 -19.00 -30.00   72
 17  \w    -74.00 -35.00   0.50    4.01    --  -47.70 -19.00-150.00   78
 18  \w   -111.00 -85.00   0.50    4.01    --  -47.70 -19.00-150.00   52
 19  \w   -121.00 -41.00   0.50    4.01    --  -47.70 -19.00 -60.00  160
 20  \w    -54.00 -27.00   0.50    4.01    --  -50.00 -78.00-167.34   54
 21  \w     31.00  63.00   0.50    4.01    --   54.00  79.00  21.89   64
 22  \w     32.00  59.00   0.50    4.01    --   54.00  76.00  60.11   54
 23  \w    -58.00 -31.00   0.50    4.01    --  -54.00 -77.00 -90.79   54
 24  \w   -112.00 -30.00   0.50    4.01    --  -54.00 -79.00 164.41  164
 25  \w     34.00  72.00   0.50    4.01    --   58.00  79.00 103.01   76
 26  \w     36.00  74.00   0.50    4.01    --   58.00  75.00 146.74   76
 27  \w    -68.00 -35.00   0.50    4.01    --  -58.00 -78.00-109.50   66
 28  \w   -121.00 -95.00   0.50    4.01    --  -58.00 -78.00-109.50   52
 29  \w     40.00  67.00   0.50    4.01    --   62.00  75.00 -21.22   54
 30  \w     39.00  64.00   0.50    4.01    --   62.00  80.00-101.04   50
 31  \w     71.00  97.00   0.50    4.01    --   62.00  80.00-101.04   52
 32  \w     38.00  65.00   0.50    4.01    --   62.00  79.00-133.97   54
 33  \w     41.00  67.00   0.50    4.01    --   62.00  74.00  66.29   52
 34  \w    -75.00 -38.00   0.50    4.01    --  -62.00 -79.00 137.92   74
 35  \w   -132.00-106.00   0.50    4.01    --  -62.00 -79.00 137.92   52
 36  \w     44.00  70.00   0.50    4.01    --   66.00  76.00  -3.20   52
 37  \w     42.00  68.00   0.50    4.01    --   66.00  79.00 -52.50   52
 38  \w     43.00  72.00   0.50    4.01    --   66.00  77.00-115.17   58
 39  \w     46.00  74.00   0.50    4.01    --   66.00  73.00 -57.23   56
 40  \w     43.00  76.00   0.50    4.01    --   66.00  78.00  70.93   66
 41  \w    -71.00 -45.00   0.50    4.01    --  -66.00 -73.00   4.45   52
 42  \w    -74.00 -43.00   0.50    4.01    --  -66.00 -77.00 166.99   62
 43  \w     47.00  73.00   0.50    4.01    --   70.00  77.00 173.36   52
 44  \w    -78.00 -52.00   0.50   15.53    --  -74.00 -74.00-120.63   52
 45  \w    -78.00 -52.00   0.50   15.53    --  -74.00 -75.00 -53.16   52
 46  \w    -79.00 -53.00   0.50   15.53    --  -74.00 -72.00  27.47   52
 47  \w    -80.00 -54.00   0.50   15.53    --  -74.00 -73.00 126.41   52
 48  \w    -82.00 -52.00   0.50   15.53    --  -74.00 -75.00 120.04   60
 49  \w    -80.00 -54.00   0.50   15.53    --  -78.00 -79.00 -63.96   52
 50  \w    -82.00 -56.00   0.50   15.53    --  -78.00 -74.00 -10.54   52
 51  \w    -83.00 -57.00   0.50   15.53    --  -78.00 -73.00   5.47   52
 52  \w    -82.00 -56.00   0.50   15.53    --  -78.00 -75.00 -26.61   52
 53  \w    -82.00 -56.00   0.50   15.53    --  -78.00 -74.00 104.59   52
 54  \w    -95.00 -54.00   0.50   15.53    --  -78.00 -79.00  86.15   82
 55  \w    -85.00 -57.00   0.50   15.53    --  -78.00 -73.00 -99.31   56
 56  \w   -112.00 -56.00   0.50   15.53    --  -78.00 -75.00-150.24  112
 57  \w    -87.00 -61.00   0.50   15.53    --  -82.00 -75.00  64.74   52
 58  \w    -95.00 -64.00   0.50   15.53    --  -86.00 -74.00  77.75   62
 59  \w    -89.00 -63.00   0.50   15.53    --  -86.00 -76.00-126.31   52
 60  \w   -102.00 -63.00   0.50   15.53    --  -86.00 -76.00-155.85   78
 61  \w    -87.00 -62.00   0.50   15.53    --  -86.25 -80.00  26.25   50
 62  \w    -91.00 -65.00   0.50   15.53    --  -86.25 -74.00  45.82   52
 63  \w    -90.00 -63.00   0.50   15.53    --  -86.25 -77.00  60.00   54
 64  \w    -90.00 -64.00   0.50   15.53    --  -86.25 -77.00 120.00   52
 65  \w    -88.00 -62.00   0.50   15.53    --  -86.25 -80.00 140.92   52
 66  \w    -98.00 -65.00   0.50   15.53    --  -86.25 -74.00 153.30   66
 67  \w    -92.00 -65.00   0.50   15.53    --  -86.25 -74.00  35.15   54
 68  \w    -91.00 -65.00   0.50   15.53    --  -86.25 -72.00 -13.05   52
 69  \w    -90.00 -63.00   0.50   15.53    --  -86.25 -77.00 -34.29   54
 70  \w    -93.00 -65.00   0.50   15.53    --  -86.25 -75.00 -80.80   56
 71  \w    -90.00 -64.00   0.50   15.53    --  -86.25 -75.00-114.12   52
 72  \w    -97.00 -65.00   0.50   15.53    --  -86.25 -73.00-170.77   64
 73  \w   -101.00 -63.00   0.50   15.53    --  -86.25 -77.00 -60.00   76
 74  \w    -72.00 -47.00   0.50   15.53    --  -86.25 108.00-123.00   50
 75  \w   -122.00 -63.00   0.50   15.53    --  -86.25 -78.00 109.02  118
 76  \w   -145.00-120.00   0.50   15.53    --  -86.25-108.00 138.00   50
 77  \w   -156.00-129.00   0.50   15.53    --  -86.25 -80.00  26.25   54
 78  \w   -143.00 -63.00   0.50   15.53    --  -86.25 -77.00-180.00  160
 79  \w     81.00 170.00   0.50   15.53    --  102.00  76.00-164.38  178
 80  \w    130.00 174.00   0.50   15.53    --  102.00  77.00-139.52   88
 81  \w     79.00 105.00   0.50   15.53    --  102.00  78.00 -90.88   52
 82  \w     79.00 105.00   0.50   15.53    --  102.00  77.00-139.52   52
 83  \w     48.00 120.00   0.50   15.53    --  106.00-136.00  53.41  144
 84  \w    143.00 176.00   0.50   15.53    --  107.75  77.00-120.00   66
 85  \w    138.00 175.00   0.50   15.53    --  107.75  15.00-120.00   74
 86  \w    138.00 165.00   0.50   15.53    --  107.75  61.00 -90.00   54
 87  \w    143.00 178.00   0.50   15.53    --  107.75  61.00-120.00   70
 88  \w    130.00 178.00   0.50   15.53    --  107.75  77.00 -30.00   96
 89  \w    136.00 178.00   0.50   15.53    --  107.75  61.00  30.00   84
 90  \w    139.00 177.00   0.50   15.53    --  107.75  15.00  30.00   76
 91  \w    143.00 175.00   0.50   15.53    --  107.75  61.00  60.00   64
 92  \w    128.00 165.00   0.50   15.53    --  107.75  45.00  60.00   74
 93  \w    120.00 174.00   0.50   15.53    --  107.75  77.00 120.00  108
 94  \w    115.00 176.00   0.50   15.53    --  107.75 125.00  90.00  122
 95  \w     95.00 126.00   0.50   15.53    --  107.75  15.00  30.00   62
 96  \w     87.00 144.00   0.50   15.53    --  107.75  77.00  30.00  114
 97  \w     91.00 169.00   0.50   15.53    --  107.75  61.00 -60.00  156
 98  \w    104.00 176.00   0.50   15.53    --  107.75 108.00-123.00  144
 99  \w     96.00 137.00   0.50   15.53    --  107.75  45.00-120.00   82
100  \w     94.00 129.00   0.50   15.53    --  107.75  61.00-120.00   70
101  \w     85.00 141.00   0.50   15.53    --  107.75  77.00-180.00  112
102  \w     86.00 140.00   0.50   15.53    --  107.75  77.00 -90.00  108
103  \w     96.00 135.00   0.50   15.53    --  107.75  15.00-120.00   78
104  \w     91.00 122.00   0.50   15.53    --  107.75  61.00 -90.00   62
105  \w     91.00 162.00   0.50   15.53    --  107.75  61.00 -30.00  142
106  \w     92.00 129.00   0.50   15.53    --  107.75  61.00  30.00   74
107  \w     85.00 148.00   0.50   15.53    --  107.75  77.00  60.00  126
108  \w     92.00 174.00   0.50   15.53    --  107.75  61.00 150.00  164
109  \w     96.00 164.00   0.50   15.53    --  107.75 125.00 150.00  136
110  \w     96.00 148.00   0.50   15.53    --  107.75  61.00 120.00  104
111  \w     93.00 174.00   0.50   15.53    --  107.75  61.00  90.00  162
112  \w     92.00 119.00   0.50   15.53    --  107.75  61.00  60.00   54
113  \w     91.00 155.00   0.50   15.53    --  107.75  61.00   0.00  128
114  \w     85.00 178.00   0.50   15.53    --  107.75  77.00   0.00  186
115  \w     85.00 154.00   0.50   15.53    --  107.75  77.00 -60.00  138
116  \w     85.00 112.00   0.50   15.53    --  107.75  77.00 -30.00   54
117  \w     86.00 139.00   0.50   15.53    --  107.75  77.00-120.00  106
118  \w     92.00 117.00   0.50   15.53    --  107.75  61.00-180.00   50
119  \w     85.00 112.00   0.50   15.53    --  107.75  77.00 120.00   54
120  \w     85.00 144.00   0.50   15.53    --  107.75  77.00 150.00  118
121  \w     85.00 149.00   0.50   15.53    --  107.75  77.00  90.00  128
122  \w     35.00  61.00   0.50   15.53    --  107.75 -77.00 -60.00   52
123  \w     44.00  73.00   0.50   15.53    --  107.75 -94.00   0.00   58
124  \w     82.00 107.00   0.50   15.53    --  107.75-108.00 138.00   50
125  \w     70.00 102.00   0.50   15.53    --  107.75 -94.00  90.00   64
126  \w     75.00 112.00   0.50   15.53    --  107.75-125.00 120.00   74
127  \w     75.00 101.00   0.50   15.53    --  107.75 -94.00 150.00   52
128  \w     56.00 112.00   0.50   15.53    --  107.75-125.00  60.00  112
129  \w     66.00 112.00   0.50   15.53    --  107.75-125.00 -60.00   92
130  \w     82.00 107.00   0.50   15.53    --  107.75-108.00-115.12   50
131  \w     79.00 105.00   0.50   15.53    --  107.75-104.00-165.80   52
132  \w     37.00  63.00   0.50   15.53    --  107.75-104.00-165.80   52
133  \w     36.00  72.00   0.50   15.53    --  107.75-108.00-115.12   72
134  \w     36.00  94.00   0.50   15.53    --  107.75 -77.00 -90.00  116
135  \w     38.00 105.00   0.50   15.53    --  107.75 -77.00-180.00  134
136  \w     35.00 107.00   0.50   15.53    --  107.75-107.00 -85.76  144
137  \w     35.00  62.00   0.50   15.53    --  107.75 -94.00  90.00   54
138  \w     35.00 110.00   0.50   15.53    --  107.75-125.00  90.00  150
139  \w     38.00  69.00   0.50   15.53    --  107.75 -61.00  60.00   62
140  \w     35.00  88.00   0.50   15.53    --  107.75-125.00 -30.00  106
141  \w     35.00 111.00   0.50   15.53    --  107.75-125.00   0.00  152
142  \w     37.00  63.00   0.50   15.53    --  107.75-125.00 120.00   52
143  \w     35.00  61.00   0.50   15.53    --  107.75 -94.00 150.00   52
144  \w     35.00 111.00   0.50   15.53    --  107.75-125.00-180.00  152
145  \w     35.00 106.00   0.50   15.53    --  107.75 -94.00-180.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0648356000
_diffrn_orient_matrix_UB_12      0.0007089000
_diffrn_orient_matrix_UB_13      0.0842592000
_diffrn_orient_matrix_UB_21      0.1058403000
_diffrn_orient_matrix_UB_22      -0.0759320000
_diffrn_orient_matrix_UB_23      0.0111733000
_diffrn_orient_matrix_UB_31      0.0363782000
_diffrn_orient_matrix_UB_32      0.0759930000
_diffrn_orient_matrix_UB_33      0.0202911000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0901
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            124255
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         2.506
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.411
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.646
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) 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            'dark violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_description       plate
_exptl_crystal_F_000             1337
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Tetrahydrofuran'
_exptl_crystal_size_max          0.194
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1119
_refine_ls_number_reflns         12277
_refine_ls_number_restraints     793
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1319
_refine_ls_R_factor_gt           0.0917
_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^)+(0.1500P)^2^+2.3136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2569
_refine_ls_wR_factor_ref         0.2932
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7417
_reflns_number_total             12277
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02409d2.cif
_cod_data_source_block           cmpd_2K1_2K2
_cod_original_formula_sum        'C76 H92 B K1.50 N O10'
_cod_database_code               1564260
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_usercomment     JoKr018_XiJi
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.771
_diffrn_oxdiff_digest_frames
;
016ca3118f2de481c285e180fd09c5817611530f10b
;
_diffrn_oxdiff_digest_hkl
;
01f437d8b956cd7302a7bc4fcc3485b1cd99c8
;
_reflns_odcompleteness_completeness 99.95
_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. Uiso/Uaniso restraints and constraints
C1_4 \\sim O2_4 \\sim C2_4 \\sim O3_4 \\sim C3_4 \\sim O4_4 \\sim C4_4 \\sim
O5_4 \\sim C5_4 \\sim O6_4 \\sim C7_4 \\sim C8_4 \\sim C9_4 \\sim C10_4 \\sim
C11_4 \\sim C12_4 \\sim C6_4 \\sim O1_4: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
O1_8 \\sim O2_8 \\sim O3_8 \\sim O4_8 \\sim O5_8 \\sim O6_8 \\sim C1_8 \\sim
C2_8 \\sim C3_8 \\sim C4_8 \\sim C5_8 \\sim C6_8 \\sim C7_8 \\sim C8_8 \\sim
C9_8 \\sim C10_8 \\sim C11_8 \\sim C12_8: within 2A with sigma of 0.03 and
sigma for terminal atoms of 0.06
O1_5 \\sim C2_5 \\sim C3_5 \\sim C4_5 \\sim C5_5 \\sim O1_15 \\sim C2_15 \\sim
C4_15 \\sim C3_15 \\sim C5_15: within 2A with sigma of 0.003 and sigma for
terminal atoms of 0.006
Uanis(C7_1) \\sim Ueq: with sigma of 0.004 and sigma for terminal atoms of 0.008
Uanis(C5_8) \\sim Ueq, Uanis(C11_8) \\sim Ueq: with sigma of 0.003 and sigma
for terminal atoms of 0.006
Uanis(C1_6) \\sim Ueq, Uanis(C2_6) \\sim Ueq, Uanis(C3_6) \\sim Ueq,
Uanis(C4_6) \\sim Ueq, Uanis(C5_6) \\sim Ueq, Uanis(C6_6) \\sim Ueq,
Uanis(C7_6) \\sim Ueq, Uanis(C8_6) \\sim Ueq, Uanis(C9_6) \\sim Ueq,
Uanis(C1_16) \\sim Ueq, Uanis(C2_16) \\sim Ueq, Uanis(C3_16) \\sim Ueq,
Uanis(C4_16) \\sim Ueq, Uanis(C5_16) \\sim Ueq, Uanis(C6_16) \\sim Ueq,
Uanis(C7_16) \\sim Ueq, Uanis(C8_16) \\sim Ueq, Uanis(C9_16) \\sim Ueq: with
sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(C1_7) \\sim Ueq, Uanis(C2_7) \\sim Ueq, Uanis(C3_7) \\sim Ueq,
Uanis(C4_7) \\sim Ueq, Uanis(C5_7) \\sim Ueq, Uanis(C6_7) \\sim Ueq,
Uanis(C7_7) \\sim Ueq, Uanis(C8_7) \\sim Ueq, Uanis(C9_7) \\sim Ueq,
Uanis(C1_17) \\sim Ueq, Uanis(C2_17) \\sim Ueq, Uanis(C3_17) \\sim Ueq,
Uanis(C4_17) \\sim Ueq, Uanis(C5_17) \\sim Ueq, Uanis(C6_17) \\sim Ueq,
Uanis(C7_17) \\sim Ueq, Uanis(C8_17) \\sim Ueq, Uanis(C9_17) \\sim Ueq: with
sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(B1A) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(B1A) = Uanis(B1B)
3. Rigid body (RIGU) restrains
 C1_4, O2_4, C2_4, O3_4, C3_4, O4_4, C4_4, O5_4, C5_4, O6_4, C7_4, C8_4, C9_4,
 C10_4, C11_4, C12_4, C6_4, O1_4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Same fragment restrains
{O1_15, C2_15, C3_15, C4_15, C5_15}
as
{O1_5, C2_5, C3_5, C4_5, C5_5} sigma for 1-2: 0.02 1-3: 0.04
{C1_6, C2_6, C3_6, C4_6, C5_6, C6_6, C7_6, C8_6, C9_6}
{C1_6, C2_6, C3_6, C4_6, C5_6, C6_6, C7_6, C8_6, C9_6}
{C1_6, C2_6, C3_6, C4_6, C5_6, C6_6, C7_6, C8_6, C9_6}
as
{C1_6, C2_6, C3_6, C4_6, C5_6, C6_6, C7_6, C8_6, C9_6} sigma for 1-2: 0.02 1-3:
0.04
5. Others
 Sof(O1)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C3)=Sof(H3A)=
 Sof(H3B)=Sof(C5)=Sof(H5A)=Sof(H5B)=1-FVAR(1)
 Sof(O1)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(C4)=Sof(H4A)=
 Sof(H4B)=Sof(C5)=Sof(H5A)=Sof(H5B)=FVAR(1)
 Sof(B1B)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(C5)=Sof(H5)=Sof(C6)=
 Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C9)=
 Sof(H9A)=Sof(H9B)=Sof(H9C)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(C5)=
 Sof(H5)=Sof(C6)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=Sof(C8)=Sof(H8A)=Sof(H8B)=
 Sof(H8C)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=1-FVAR(2)
 Sof(B1A)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(C5)=Sof(H5)=Sof(C6)=
 Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C9)=
 Sof(H9A)=Sof(H9B)=Sof(H9C)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(C5)=
 Sof(H5)=Sof(C6)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=Sof(C8)=Sof(H8A)=Sof(H8B)=
 Sof(H8C)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=FVAR(2)
 Fixed Sof: K1(0.5) O1(0.5) O2(0.5) O3(0.5) O4(0.5) O5(0.5) O6(0.5) C1(0.5)
 H1A(0.5) H1B(0.5) C2(0.5) H2A(0.5) H2B(0.5) C3(0.5) H3A(0.5) H3B(0.5) C4(0.5)
 H4A(0.5) H4B(0.5) C5(0.5) H5A(0.5) H5B(0.5) C6(0.5) H6A(0.5) H6B(0.5) C7(0.5)
 H7A(0.5) H7B(0.5) C8(0.5) H8A(0.5) H8B(0.5) C9(0.5) H9A(0.5) H9B(0.5) C10(0.5)
 H10A(0.5) H10B(0.5) C11(0.5) H11A(0.5) H11B(0.5) C12(0.5) H12A(0.5) H12B(0.5)
6.a Ternary CH refined with riding coordinates:
 C16(H16)
6.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B),
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C6(H6A,H6B), C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B),
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,
 H11B), C12(H12A,H12B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B),
 C2(H2A,H2B), C4(H4A,H4B), C3(H3A,H3B), C5(H5A,H5B)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C2(H2), C3(H3), C5(H5), C6(H6), C2(H2),
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C15(H15), C19(H19),
 C21(H21), C22(H22), C3(H3), C5(H5), C3(H3), C5(H5), C3(H3), C5(H5), C3(H3),
 C5(H5)
6.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C7(H7A,H7B,H7C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,
 H9B,H9C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C7(H7A,H7B,H7C),
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,
 H9C)
;
_shelx_res_checksum              7680
_shelx_hkl_checksum              96891
_olex2_date_sample_data_collection 2019-10-14
_olex2_date_sample_submission    2019-10-14
_olex2_exptl_crystal_mounting_method
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
 polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
 nitrogen (Oxford Cryostream 800).
;
_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 1.561
_oxdiff_exptl_absorpt_empirical_full_min 0.664