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_7160032
_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         'C20 H12 Cl N3'
_chemical_formula_sum            'C20 H12 Cl N3'
_chemical_formula_weight         329.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-04-04
_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                 102.8862(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.66903(6)
_cell_length_b                   13.58537(6)
_cell_length_c                   11.39283(5)
_cell_measurement_reflns_used    34204
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      69.6000
_cell_measurement_theta_min      3.9380
_cell_volume                     1609.719(14)
_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  (Sheldrick, 2015)'
_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 0.995
_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    -79.00 -53.00   0.50    0.20    --  -42.75 114.00 124.00   52
  2  \w    -78.00 -47.00   0.50    0.20    --  -42.75-172.00-107.00   62
  3  \w   -115.00 -71.00   0.50    0.20    --  -42.75 172.00 -94.00   88
  4  \w     64.00  90.00   0.50    0.20    --   44.32-172.00-107.00   52
  5  \w     60.00  85.00   0.50    0.20    --   44.32 172.00 -94.00   50
  6  \w     16.00  83.00   0.50    0.20    --   44.32-114.00  33.00  134
  7  \w   -109.00 -83.00   0.50    0.50    --  -95.95 114.00 124.00   52
  8  \w    -82.00 -47.00   0.50    0.50    --  -95.95 172.00 -94.00   70
  9  \w   -131.00-105.00   0.50    0.50    --  -95.95 172.00 -94.00   52
 10  \w   -161.00-115.00   0.50    0.50    --  -95.95-114.00  33.00   92
 11  \w     73.00  98.00   0.50    0.50    --   97.51 172.00 -94.00   50
 12  \w     97.00 122.00   0.50    0.50    --   97.51 114.00 124.00   50
 13  \w     66.00 105.00   0.50    0.50    --   97.51-114.00  33.00   78
 14  \w    -54.00  -9.00   0.50    0.20    --  -10.00 119.00-122.45   90
 15  \w    -23.00   2.00   0.50    0.20    --   14.00 105.00  47.90   50
 16  \w    -54.00  -2.00   0.50    0.20    --  -14.00 111.00 159.44  104
 17  \w    -56.00 -31.00   0.50    0.20    --   14.00 159.00-133.33   50
 18  \w     -4.00  21.00   0.50    0.20    --   30.00 100.00-103.63   50
 19  \w     -4.00  21.00   0.50    0.20    --   30.00 100.00  31.34   50
 20  \w     -3.00  22.00   0.50    0.20    --   30.00  99.00  69.92   50
 21  \w     -2.00  23.00   0.50    0.20    --   30.00  96.00 168.98   50
 22  \w      2.00  27.00   0.50    0.20    --   34.00  97.00 -28.31   50
 23  \w      6.00  31.00   0.50    0.20    --   38.00  95.00 108.93   50
 24  \w      6.00  31.00   0.50    0.20    --   38.00  95.00 173.64   50
 25  \w      6.00  31.00   0.50    0.20    --   38.00  95.00  30.83   50
 26  \w      7.00  32.00   0.50    0.20    --   38.00  94.00 -68.01   50
 27  \w      6.00  31.00   0.50    0.20    --   38.00  95.00-156.52   50
 28  \w     12.00  37.00   0.50    0.20    --   42.00  90.00  -9.82   50
 29  \w     14.00  39.00   0.50    0.20    --   42.00  91.00 114.62   50
 30  \w     12.00  37.00   0.50    0.20    --   42.00  90.00-118.80   50
 31  \w    -42.00 -17.00   0.50    0.20    --  -42.75 -91.00-159.99   50
 32  \w     16.00  41.00   0.50    0.20    --   46.00  91.00-178.16   50
 33  \w     16.00  41.00   0.50    0.20    --   46.00  92.00  92.21   50
 34  \w     17.00  42.00   0.50    0.20    --   46.00  87.00 -86.15   50
 35  \w     16.00  41.00   0.50    0.20    --   46.00  92.00 159.44   50
 36  \w     16.00  41.00   0.50    0.20    --   46.00  91.00  24.51   50
 37  \w     17.00  42.00   0.50    0.20    --   46.00  88.00 -49.99   50
 38  \w     16.00  41.00   0.50    0.20    --   46.00  91.00  69.74   50
 39  \w     16.00  41.00   0.50    0.20    --   46.00  90.00   9.93   50
 40  \w    -76.00 -31.00   0.50    0.20    --  -54.00 -71.00 129.27   90
 41  \w   -119.00 -93.00   0.50    0.20    --  -54.00 -73.00 163.41   52
 42  \w    -64.00 -33.00   0.50    0.20    --  -54.00 -70.00-171.46   62
 43  \w     66.00  92.00   0.50    0.20    --   54.00  77.00  31.54   52
 44  \w     30.00  56.00   0.50    0.20    --   54.00  77.00  31.54   52
 45  \w    -55.00 -30.00   0.50    0.20    --  -54.00 -73.00 163.41   50
 46  \w    -55.00 -29.00   0.50    0.20    --  -54.00 -76.00  39.39   52
 47  \w    -57.00 -31.00   0.50    0.20    --  -54.00 -72.00  -5.54   52
 48  \w   -113.00 -72.00   0.50    0.20    --  -54.00 -74.00 -84.88   82
 49  \w   -110.00 -84.00   0.50    0.20    --  -54.00 -76.00  39.39   52
 50  \w    -58.00 -30.00   0.50    0.20    --  -54.00 -74.00 -84.88   56
 51  \w    -71.00 -33.00   0.50    0.20    --  -58.00 -76.00  84.09   76
 52  \w     39.00  65.00   0.50    0.20    --   58.00  75.00 -25.03   52
 53  \w    -63.00 -37.00   0.50    0.20    --  -58.00 -71.00-121.70   52
 54  \w     33.00  97.00   0.50    0.20    --   58.00  77.00 173.89  128
 55  \w    -70.00 -40.00   0.50    0.20    --  -62.00 -69.00-143.80   60
 56  \w    -64.00 -39.00   0.50    0.20    --  -62.00 -69.00  17.23   50
 57  \w    -64.00 -39.00   0.50    0.20    --  -62.00 -70.00 -98.09   50
 58  \w   -102.00 -70.00   0.50    0.20    --  -62.00 -69.00  17.23   64
 59  \w    -63.00 -37.00   0.50    0.20    --  -62.00 -76.00  58.75   52
 60  \w    -68.00 -39.00   0.50    0.20    --  -62.00 -72.00  -9.58   58
 61  \w    -70.00 -41.00   0.50    0.20    --  -66.00 -75.00  42.55   58
 62  \w   -128.00 -43.00   0.50    0.20    --  -66.00 -69.00 129.82  170
 63  \w    -73.00 -41.00   0.50    0.20    --  -66.00 -76.00 -25.32   64
 64  \w    -78.00 -45.00   0.50    0.50    --  -70.00 -77.00-157.02   66
 65  \w   -107.00 -45.00   0.50    0.50    --  -70.00 -76.00 -35.79  124
 66  \w   -123.00 -97.00   0.50    0.50    --  -74.00 -76.00 -82.66   52
 67  \w    -75.00 -49.00   0.50    0.50    --  -74.00 -76.00 -82.66   52
 68  \w    -82.00 -51.00   0.50    0.50    --  -74.00 -72.00 -70.31   62
 69  \w    -81.00 -50.00   0.50    0.50    --  -74.00 -74.00-175.47   62
 70  \w    -82.00 -49.00   0.50    0.50    --  -74.00 -76.00-101.65   66
 71  \w   -140.00 -91.00   0.50    0.50    --  -74.00 -76.00-101.65   98
 72  \w    -79.00 -54.00   0.50    0.50    --  -78.00 -72.00  21.90   50
 73  \w    -90.00 -54.00   0.50    0.50    --  -78.00 -74.00 128.31   72
 74  \w    -94.00 -53.00   0.50    0.50    --  -78.00 -77.00 175.30   82
 75  \w    -78.00 -53.00   0.50    0.50    --  -78.00 -76.00 100.70   50
 76  \w    -87.00 -53.00   0.50    0.50    --  -78.00 -75.00-119.07   68
 77  \w   -133.00 -85.00   0.50    0.50    --  -78.00 -72.00  21.90   96
 78  \w    -90.00 -55.00   0.50    0.50    --  -78.00 -77.00  81.75   70
 79  \w   -123.00 -97.00   0.50    0.50    --  -78.00 -77.00  81.75   52
 80  \w    -87.00 -57.00   0.50    0.50    --  -82.00 -77.00 115.13   60
 81  \w    -92.00 -57.00   0.50    0.50    --  -82.00 -77.00 -96.20   70
 82  \w    -84.00 -59.00   0.50    0.50    --  -82.00 -75.00   8.88   50
 83  \w    -99.00 -57.00   0.50    0.50    --  -82.00 -76.00  49.70   84
 84  \w   -144.00 -58.00   0.50    0.50    --  -82.00 -74.00-133.39  172
 85  \w   -146.00-100.00   0.50    0.50    --  -82.00 -77.00 -17.89   92
 86  \w    -94.00 -57.00   0.50    0.50    --  -82.00 -77.00 -17.89   74
 87  \w    -86.00 -57.00   0.50    0.50    --  -82.00 -76.00 -43.07   58
 88  \w   -109.00 -64.00   0.50    0.50    --  -86.00 -71.00 -64.41   90
 89  \w    -92.00 -66.00   0.50    0.50    --  -86.00 -70.00 129.88   52
 90  \w   -152.00-115.00   0.50    0.50    --  -86.00 -71.00 -64.41   74
 91  \w   -145.00 -63.00   0.50    0.50    --  -86.00 -77.00-173.47  164
 92  \w   -153.00-127.00   0.50    0.50    --  -90.00 -76.00  38.14   52
 93  \w   -149.00 -70.00   0.50    0.50    --  -90.00 -59.00 105.08  158
 94  \w   -106.00 -65.00   0.50    0.50    --  -90.00 -76.00  38.14   82
 95  \w    -90.00 -65.00   0.50    0.50    --  -90.00 -76.00   2.50   50
 96  \w   -157.00-101.00   0.50    0.50    --  -90.00 -76.00   2.50  112
 97  \w    -95.00 -69.00   0.50    0.50    --  -94.00 -76.00 170.22   52
 98  \w   -161.00 -71.00   0.50    0.50    --  -94.00 -69.00-108.01  180
 99  \w    -96.00 -71.00   0.50    0.50    --  -94.00 -71.00 -30.64   50
100  \w   -160.00-121.00   0.50    0.50    --  -94.00 -71.00 -30.64   78
101  \w   -138.00 -71.00   0.50    0.50    --  -95.95 -77.00-150.00  134
102  \w    -57.00 -32.00   0.50    0.50    --  -95.95  50.00 120.00   50
103  \w    -98.00 -73.00   0.50    0.50    --  -95.95 -77.00-120.00   50
104  \w   -128.00-102.00   0.50    0.50    --  -95.95 -77.00-120.00   52
105  \w   -137.00 -74.00   0.50    0.50    --  -95.95 -68.00 120.00  126
106  \w   -125.00 -90.00   0.50    0.50    --  -95.95 142.00-168.32   70
107  \w    -80.00 -29.00   0.50    0.50    --  -95.95  68.00 150.00  102
108  \w   -156.00 -75.00   0.50    0.50    --  -95.95 -68.00 150.00  162
109  \w   -163.00 -71.00   0.50    0.50    --  -95.95 -76.00-132.87  184
110  \w    -74.00 -37.00   0.50    0.50    --  -95.95 142.00-168.32   74
111  \w   -135.00 -80.00   0.50    0.50    --  -95.95 -59.00 -90.00  110
112  \w   -161.00 -74.00   0.50    0.50    --  -95.95 -68.00  60.00  174
113  \w    -57.00 -30.00   0.50    0.50    --  -95.95  50.00 150.00   54
114  \w   -101.00 -76.00   0.50    0.50    --  -95.95 -68.00 -90.00   50
115  \w   -123.00 -71.00   0.50    0.50    --  -95.95 -77.00  30.00  104
116  \w    -69.00 -27.00   0.50    0.50    --  -95.95  96.00 -90.00   84
117  \w   -112.00 -71.00   0.50    0.50    --  -95.95 -77.00-180.00   82
118  \w   -155.00-124.00   0.50    0.50    --  -95.95 -77.00-180.00   62
119  \w    -56.00 -30.00   0.50    0.50    --  -95.95  50.00 -90.00   52
120  \w   -162.00-103.00   0.50    0.50    --  -95.95 -59.00 -60.00  118
121  \w    -57.00 -31.00   0.50    0.50    --  -95.95  50.00 -60.00   52
122  \w   -153.00 -71.00   0.50    0.50    --  -95.95 -77.00  90.00  164
123  \w   -162.00-118.00   0.50    0.50    --  -95.95 -42.00 -30.00   88
124  \w    -83.00 -46.00   0.50    0.50    --  -95.95  68.00 -30.00   74
125  \w    125.00 150.00   0.50    0.50    --   97.51  77.00 -60.00   50
126  \w     50.00 104.00   0.50    0.50    --   97.51 -77.00  60.00  108
127  \w     73.00 118.00   0.50    0.50    --   97.51  77.00 -60.00   90
128  \w    128.00 164.00   0.50    0.50    --   97.51  77.00-150.00   72
129  \w     73.00  98.00   0.50    0.50    --   97.51  77.00-150.00   50
130  \w     32.00  69.00   0.50    0.50    --   97.51 -59.00-180.00   74
131  \w     49.00 107.00   0.50    0.50    --   97.51-117.00-150.00  116
132  \w     73.00 156.00   0.50    0.50    --   97.51  77.00 -30.00  166
133  \w     52.00  90.00   0.50    0.50    --   97.51 -96.00-150.00   76
134  \w     32.00 126.00   0.50    0.50    --   97.51-145.00  30.00  188
135  \w    122.00 151.00   0.50    0.50    --   97.51  77.00  60.00   58
136  \w     73.00  99.00   0.50    0.50    --   97.51  77.00  60.00   52
137  \w     36.00 107.00   0.50    0.50    --   97.51-117.00  90.00  142
138  \w    140.00 165.00   0.50    0.50    --   97.51  77.00   0.00   50
139  \w     73.00 131.00   0.50    0.50    --   97.51  77.00   0.00  116
140  \w     36.00  83.00   0.50    0.50    --   97.51 -68.00 -30.00   94
141  \w     32.00  68.00   0.50    0.50    --   97.51 -59.00   0.00   72
142  \w     56.00  83.00   0.50    0.50    --   97.51 -68.00-150.00   54
143  \w    137.00 162.00   0.50    0.50    --   97.51  68.00 120.00   50
144  \w     79.00 117.00   0.50    0.50    --   97.51  68.00 120.00   76
145  \w     67.00  92.00   0.50    0.50    --   97.51-172.00-107.00   50
;
_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  0.0278
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            38364
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.745
_diffrn_reflns_theta_min         3.980
_exptl_absorpt_coefficient_mu    2.128
_exptl_absorpt_correction_T_max  0.611
_exptl_absorpt_correction_T_min  0.406
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (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    1.361
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.166
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 2811 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         6013
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0242
_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^)+(0.0383P)^2^+0.3430P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0621
_reflns_Friedel_coverage         0.904
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                5989
_reflns_number_total             6013
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00863d3.cif
_cod_data_source_block           in_2022_281
_cod_depositor_comments
'Adding full bibliography for 7160032--7160033.cif.'
_cod_original_cell_volume        1609.720(13)
_cod_database_code               7160032
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C4A(H4A), C13(H13), C9A(H9A), C18A(H18A), C17(H17),
 C11(H11), C9(H9), C12A(H12A), C2A(H2A), C18(H18), C13A(H13A), C4(H4), C2(H2),
 C15A(H15A), C10A(H10A), C12(H12), C11A(H11A), C3(H3), C17A(H17A), C10(H10),
 C16A(H16A), C3A(H3A)
;
_shelx_res_checksum              4932
_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
;