Atropisomeric 1-phenylbenzimidazoles affecting microtubule organization: influence of axial chirality.
Pospíšilová, Jana; Heger, Tomáš; Kurka, Ondřej; Kvasnicová, Marie; Chládková, Anna; Nemec, Ivan; Rárová, Lucie; Cankař, Petr; Organic & biomolecular chemistry 22 (2024) 6966–6980; doi:10.1039/d4ob00863d

data_7160033
_publ_section_title
;
 Atropisomeric 1-phenylbenzimidazoles affecting microtubule organization:
 influence of axial chirality.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6966
_journal_page_last               6980
_journal_paper_doi               10.1039/d4ob00863d
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C19 H12 Cl I N2'
_chemical_formula_sum            'C19 H12 Cl I N2'
_chemical_formula_weight         430.66
_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
_audit_creation_date             2023-03-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-07-28 deposited with the CCDC.	2024-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.66885(4)
_cell_length_b                   10.22838(6)
_cell_length_c                   18.76755(10)
_cell_measurement_reflns_used    37492
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      69.6070
_cell_measurement_theta_min      4.2990
_cell_volume                     1664.087(15)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (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  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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   -102.00 -64.00   0.50    0.20    --  -42.75 -66.00-108.00   76
  2  \w     74.00 108.00   0.50    0.20    --   44.32  66.00  26.00   68
  3  \w     22.00  48.00   0.50    0.20    --   44.32 -66.00-108.00   52
  4  \w   -103.00 -76.00   0.50    0.60    --  -95.95 -66.00-108.00   54
  5  \w    -78.00 -53.00   0.50    0.60    --  -95.95  66.00  26.00   50
  6  \w   -142.00-116.00   0.50    0.60    --  -95.95 -66.00-108.00   52
  7  \w     30.00  68.00   0.50    0.60    --   97.51 -66.00-108.00   76
  8  \w    121.00 147.00   0.50    0.60    --   97.51  66.00  26.00   52
  9  \w    -57.00 -32.00   0.50    0.20    --   14.00 162.00 -68.81   50
 10  \w    -59.00 -10.00   0.50    0.20    --  -14.00 120.00 171.53   98
 11  \w    -23.00   2.00   0.50    0.20    --   14.00 106.00 127.48   50
 12  \w    -69.00 -15.00   0.50    0.20    --  -18.00 130.00  38.29  108
 13  \w     -8.00  17.00   0.50    0.20    --   26.00 100.00 174.13   50
 14  \w     -3.00  22.00   0.50    0.20    --   30.00  98.00  15.36   50
 15  \w     -1.00  24.00   0.50    0.20    --   30.00  99.00  45.81   50
 16  \w      2.00  27.00   0.50    0.20    --   34.00  96.00 104.70   50
 17  \w      1.00  26.00   0.50    0.20    --   34.00  98.00-178.62   50
 18  \w      1.00  26.00   0.50    0.20    --   34.00  98.00  13.76   50
 19  \w      7.00  32.00   0.50    0.20    --   38.00  94.00 -99.64   50
 20  \w      9.00  34.00   0.50    0.20    --   38.00  89.00 -33.41   50
 21  \w      7.00  32.00   0.50    0.20    --   38.00  93.00 150.97   50
 22  \w    -32.00  -7.00   0.50    0.20    --  -38.00 -94.00 -27.11   50
 23  \w    -41.00 -12.00   0.50    0.20    --  -42.00 -91.00  49.02   58
 24  \w     13.00  38.00   0.50    0.20    --   42.00  89.00  12.44   50
 25  \w     13.00  38.00   0.50    0.20    --   42.00  87.00 -14.84   50
 26  \w    -67.00 -41.00   0.50    0.20    --  -42.75 138.00  90.00   52
 27  \w    -61.00  -9.00   0.50    0.20    --  -42.75  66.00  26.00  104
 28  \w     -1.00  25.00   0.50    0.20    --  -42.75  66.00  26.00   52
 29  \w    -76.00   4.00   0.50    0.20    --  -42.75 104.00 -30.00  160
 30  \w     16.00  41.00   0.50    0.20    --   46.00  90.00 178.67   50
 31  \w     16.00  41.00   0.50    0.20    --   46.00  91.00 152.99   50
 32  \w    -43.00 -18.00   0.50    0.20    --  -46.00 -90.00  54.55   50
 33  \w     16.00  41.00   0.50    0.20    --   46.00  90.00 129.26   50
 34  \w    -42.00 -16.00   0.50    0.20    --  -46.00 -91.00   8.39   52
 35  \w     16.00  41.00   0.50    0.20    --   46.00  92.00-141.66   50
 36  \w     16.00  41.00   0.50    0.20    --   46.00  92.00 -84.07   50
 37  \w    -52.00 -26.00   0.50    0.20    --  -50.00 -72.00 -69.24   52
 38  \w    -52.00 -27.00   0.50    0.20    --  -50.00 -71.00 148.45   50
 39  \w    -58.00 -32.00   0.50    0.20    --  -54.00 -74.00 -42.27   52
 40  \w    -61.00 -31.00   0.50    0.20    --  -54.00 -71.00-109.79   60
 41  \w    -56.00 -30.00   0.50    0.20    --  -54.00 -74.00 114.02   52
 42  \w    -67.00 -34.00   0.50    0.20    --  -58.00 -73.00-163.84   66
 43  \w    -60.00 -35.00   0.50    0.20    --  -58.00 -70.00 -31.48   50
 44  \w    -60.00 -35.00   0.50    0.20    --  -58.00 -69.00 -85.90   50
 45  \w    -61.00 -34.00   0.50    0.20    --  -58.00 -74.00  98.60   54
 46  \w     33.00  58.00   0.50    0.20    --   58.00  77.00 -67.93   50
 47  \w    -69.00 -34.00   0.50    0.20    --  -58.00 -75.00 149.97   70
 48  \w    -60.00 -35.00   0.50    0.20    --  -58.00 -72.00-146.32   50
 49  \w    -90.00 -36.00   0.50    0.20    --  -58.00 -71.00 177.54  108
 50  \w    -65.00 -39.00   0.50    0.20    --  -62.00 -71.00  29.12   52
 51  \w   -108.00 -83.00   0.50    0.20    --  -62.00 -70.00 -63.21   50
 52  \w    -79.00 -37.00   0.50    0.20    --  -62.00 -77.00  93.49   84
 53  \w   -126.00 -86.00   0.50    0.20    --  -62.00 -77.00  93.49   80
 54  \w    -65.00 -39.00   0.50    0.20    --  -62.00 -70.00 -63.21   52
 55  \w    -98.00 -43.00   0.50    0.20    --  -66.00 -77.00  31.35  110
 56  \w    -68.00 -42.00   0.50    0.20    --  -66.00 -76.00 168.75   52
 57  \w    -99.00 -47.00   0.50    0.60    --  -70.00 -71.00-108.83  104
 58  \w    -77.00 -45.00   0.50    0.60    --  -70.00 -76.00 137.37   64
 59  \w    -80.00 -45.00   0.50    0.60    --  -70.00 -76.00  68.34   70
 60  \w    -76.00 -48.00   0.50    0.60    --  -70.00 -77.00 -20.71   56
 61  \w    -74.00 -47.00   0.50    0.60    --  -70.00 -77.00  19.76   54
 62  \w   -137.00-111.00   0.50    0.60    --  -70.00 -77.00 -20.71   52
 63  \w   -138.00 -80.00   0.50    0.60    --  -70.00 -77.00  19.76  116
 64  \w    -83.00 -49.00   0.50    0.60    --  -74.00 -75.00  87.97   68
 65  \w    -75.00 -50.00   0.50    0.60    --  -74.00 -75.00-108.93   50
 66  \w    -98.00 -52.00   0.50    0.60    --  -74.00 -76.00 117.32   92
 67  \w    -91.00 -50.00   0.50    0.60    --  -74.00 -73.00-177.90   82
 68  \w    -92.00 -50.00   0.50    0.60    --  -74.00 -72.00 -58.08   84
 69  \w    -89.00 -50.00   0.50    0.60    --  -74.00 -76.00 -70.94   78
 70  \w    -97.00 -49.00   0.50    0.60    --  -74.00 -77.00-148.47   96
 71  \w   -139.00-113.00   0.50    0.60    --  -74.00 -77.00-148.47   52
 72  \w    -78.00 -50.00   0.50    0.60    --  -74.00 -72.00-140.59   56
 73  \w    -86.00 -53.00   0.50    0.60    --  -78.00 -75.00  52.39   66
 74  \w    -88.00 -55.00   0.50    0.60    --  -78.00 -73.00   5.07   66
 75  \w    -86.00 -55.00   0.50    0.60    --  -78.00 -73.00  34.71   62
 76  \w    -99.00 -53.00   0.50    0.60    --  -78.00 -76.00 -79.80   92
 77  \w    -93.00 -59.00   0.50    0.60    --  -82.00 -75.00  -3.29   68
 78  \w   -117.00 -58.00   0.50    0.60    --  -82.00 -74.00 -99.57  118
 79  \w    -95.00 -59.00   0.50    0.60    --  -82.00 -74.00 175.37   72
 80  \w   -147.00-121.00   0.50    0.60    --  -82.00 -75.00-153.27   52
 81  \w    -89.00 -57.00   0.50    0.60    --  -82.00 -77.00 114.51   64
 82  \w   -132.00 -59.00   0.50    0.60    --  -82.00 -76.00 -25.33  146
 83  \w    -96.00 -57.00   0.50    0.60    --  -82.00 -75.00  77.64   78
 84  \w   -141.00 -57.00   0.50    0.60    --  -82.00 -75.00 132.29  168
 85  \w    -82.00 -57.00   0.50    0.60    --  -82.00 -75.00-153.27   50
 86  \w   -108.00 -58.00   0.50    0.60    --  -82.00 -73.00 152.13  100
 87  \w   -132.00 -65.00   0.50    0.60    --  -86.00 -65.00-128.56  134
 88  \w    108.00 134.00   0.50    0.60    --   86.00  72.00  51.73   52
 89  \w     63.00  89.00   0.50    0.60    --   86.00  72.00  51.73   52
 90  \w   -109.00 -67.00   0.50    0.60    --  -90.00 -69.00  -5.50   84
 91  \w   -105.00 -67.00   0.50    0.60    --  -90.00 -69.00-154.28   76
 92  \w    -98.00 -65.00   0.50    0.60    --  -90.00 -77.00  71.84   66
 93  \w   -155.00-111.00   0.50    0.60    --  -90.00 -77.00  71.84   88
 94  \w    -99.00 -66.00   0.50    0.60    --  -90.00 -74.00 106.12   66
 95  \w    -93.00 -67.00   0.50    0.60    --  -90.00 -74.00  84.95   52
 96  \w   -119.00 -72.00   0.50    0.60    --  -94.00 -66.00 -65.10   94
 97  \w    -94.00 -69.00   0.50    0.60    --  -94.00 -75.00-122.28   50
 98  \w   -154.00 -77.00   0.50    0.60    --  -95.95 -68.00 120.00  154
 99  \w   -134.00 -74.00   0.50    0.60    --  -95.95 -68.00  30.00  120
100  \w   -110.00 -31.00   0.50    0.60    --  -95.95 117.00 -60.00  158
101  \w   -112.00 -74.00   0.50    0.60    --  -95.95 -67.00 112.42   76
102  \w   -160.00 -74.00   0.50    0.60    --  -95.95 -77.00-180.00  172
103  \w   -125.00 -74.00   0.50    0.60    --  -95.95 -73.00  82.75  102
104  \w    -56.00 -29.00   0.50    0.60    --  -95.95  50.00-150.00   54
105  \w   -110.00 -72.00   0.50    0.60    --  -95.95 117.00-180.00   76
106  \w   -110.00 -38.00   0.50    0.60    --  -95.95 117.00 -90.00  144
107  \w   -124.00 -73.00   0.50    0.60    --  -95.95 -77.00 -60.00  102
108  \w   -164.00-130.00   0.50    0.60    --  -95.95 -77.00 -60.00   68
109  \w    -57.00 -29.00   0.50    0.60    --  -95.95  50.00-180.00   56
110  \w    -66.00 -37.00   0.50    0.60    --  -95.95 117.00 120.00   58
111  \w    -56.00 -31.00   0.50    0.60    --  -95.95 117.00  90.00   50
112  \w   -127.00-102.00   0.50    0.60    --  -95.95 -17.00 150.00   50
113  \w    -93.00 -67.00   0.50    0.60    --  -95.95 117.00 120.00   52
114  \w   -107.00 -71.00   0.50    0.60    --  -95.95 117.00  90.00   72
115  \w   -157.00 -74.00   0.50    0.60    --  -95.95 -68.00 150.00  166
116  \w   -104.00 -72.00   0.50    0.60    --  -95.95 -77.00 -30.00   64
117  \w   -133.00-107.00   0.50    0.60    --  -95.95 -77.00 -30.00   52
118  \w   -164.00-138.00   0.50    0.60    --  -95.95 -17.00 150.00   52
119  \w     73.00 147.00   0.50    0.60    --   97.51  77.00-150.00  148
120  \w     31.00  56.00   0.50    0.60    --   97.51 -50.00-150.00   50
121  \w     81.00 141.00   0.50    0.60    --   97.51  59.00  90.00  120
122  \w     75.00 123.00   0.50    0.60    --   97.51  68.00-150.00   96
123  \w     75.00 109.00   0.50    0.60    --   97.51-117.00  90.00   68
124  \w     32.00  57.00   0.50    0.60    --   97.51 -50.00 -90.00   50
125  \w     33.00  59.00   0.50    0.60    --   97.51-117.00  90.00   52
126  \w     66.00 109.00   0.50    0.60    --   97.51-117.00  30.00   86
127  \w     96.00 131.00   0.50    0.60    --   97.51  68.00   0.00   70
128  \w     28.00  85.00   0.50    0.60    --   97.51 -96.00  30.00  114
129  \w     79.00 163.00   0.50    0.60    --   97.51  68.00 -30.00  168
130  \w     74.00 160.00   0.50    0.60    --   97.51  77.00 150.00  172
131  \w     29.00  74.00   0.50    0.60    --   97.51 -77.00  30.00   90
132  \w     33.00  77.00   0.50    0.60    --   97.51 -68.00  60.00   88
133  \w     74.00 159.00   0.50    0.60    --   97.51  77.00   0.00  170
134  \w    104.00 164.00   0.50    0.60    --   97.51  59.00 -90.00  120
135  \w     40.00  69.00   0.50    0.60    --   97.51 -59.00 150.00   58
136  \w     29.00 101.00   0.50    0.60    --   97.51 -77.00-150.00  144
137  \w     73.00 161.00   0.50    0.60    --   97.51  77.00-180.00  176
138  \w     73.00 151.00   0.50    0.60    --   97.51  77.00  30.00  156
139  \w     31.00 105.00   0.50    0.60    --   97.51 -77.00 120.00  148
140  \w     73.00 164.00   0.50    0.60    --   97.51  77.00-120.00  182
141  \w     73.00 158.00   0.50    0.60    --   97.51  77.00  60.00  170
142  \w     75.00 157.00   0.50    0.60    --   97.51  68.00 -60.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            41402
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.713
_diffrn_reflns_theta_min         4.712
_exptl_absorpt_coefficient_mu    16.586
_exptl_absorpt_correction_T_max  0.527
_exptl_absorpt_correction_T_min  0.053
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (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    1.719
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.732
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 1310 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0174
_refine_ls_R_factor_gt           0.0174
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0270P)^2^+0.8347P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0460
_refine_ls_wR_factor_ref         0.0460
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3139
_reflns_number_total             3139
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00863d3.cif
_cod_data_source_block           in_2022_282
_cod_depositor_comments
'Adding full bibliography for 7160032--7160033.cif.'
_cod_original_cell_volume        1664.085(15)
_cod_database_code               7160033
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.222
_shelx_estimated_absorpt_t_min   0.086
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C13(H13), C5(H5), C6(H6), C18(H18), C4(H4), C14(H14),
 C20(H20), C17(H17), C19(H19), C16(H16)
;
_shelx_res_checksum              64520
_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
;