#------------------------------------------------------------------------------
#$Date: 2025-04-05 07:10:43 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299129 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/03/7160366.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7160366
loop_
_publ_author_name
'Toman, Daniel'
'Nemec, Ivan'
'Kurka, Ondřej'
'Přibylka, Adam'
'Cankař, Petr'
_publ_section_title
;
 Axially chiral dimethylaminobenzimidazoles and their preliminary
 evaluation as acyl-transfer reagents.
;
_journal_issue                   11
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2672
_journal_page_last               2682
_journal_paper_doi               10.1039/d4ob02052a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C23 H24 N4, C2 H6 O'
_chemical_formula_sum            'C25 H30 N4 O'
_chemical_formula_weight         402.53
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2024-11-26
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2024-12-02 deposited with the CCDC.	2025-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.455(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.4550(2)
_cell_length_b                   13.9094(2)
_cell_length_c                   10.4634(2)
_cell_measurement_reflns_used    13763
_cell_measurement_temperature    89.9(4)
_cell_measurement_theta_max      68.2460
_cell_measurement_theta_min      4.2150
_cell_volume                     1083.03(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.115a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 42.57a 64-bit (release 20-05-2022))'
_computing_data_reduction        'CrysAlisPro 1.171.43.115a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      89.9(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00 -24.00   0.50    2.00    --  -42.75 136.00 -45.00   58
  2  ω    -91.00 -57.00   0.50    2.00    --  -42.75 136.00 -45.00   68
  3  ω    -64.00 -24.00   0.50    2.00    --  -42.75 133.00 136.00   80
  4  ω     34.00  99.00   0.50    2.00    --   44.32-136.00-110.00  130
  5  ω     31.00  58.00   0.50    2.00    --   44.32-133.00  67.00   54
  6  ω    -99.00 -74.00   0.50    6.20    --  -93.31 136.00 -45.00   50
  7  ω   -130.00-105.00   0.50    6.20    --  -93.31-136.00-110.00   50
  8  ω    -94.00 -67.00   0.50    6.20    --  -93.31 133.00 136.00   54
  9  ω     74.00 108.00   0.50    6.20    --   94.87-133.00  67.00   68
 10  ω     94.00 121.00   0.50    6.20    --   94.87 136.00 -45.00   54
 11  ω     90.00 115.00   0.50    6.20    --   94.87 133.00 136.00   50
 12  ω     66.00 120.00   0.50    6.20    --   94.87-136.00-110.00  108
 13  ω    -55.00 -16.00   0.50    2.00    --   -4.00 129.00  56.70   78
 14  ω    -35.00 -10.00   0.50    2.00    --    8.00 118.00-127.58   50
 15  ω    -12.00  14.00   0.50    2.00    --   20.00 100.00  62.69   52
 16  ω     -9.00  16.00   0.50    2.00    --   24.00 101.00-126.93   50
 17  ω      4.00  29.00   0.50    2.00    --   36.00  96.00  82.18   50
 18  ω      5.00  30.00   0.50    2.00    --   36.00  94.00  32.07   50
 19  ω      4.00  30.00   0.50    2.00    --   36.00  96.00-162.82   52
 20  ω      4.00  29.00   0.50    2.00    --   36.00  95.00 134.90   50
 21  ω      4.00  29.00   0.50    2.00    --   36.00  96.00 -18.87   50
 22  ω     12.00  39.00   0.50    2.00    --   40.00  89.00 169.33   54
 23  ω     12.00  37.00   0.50    2.00    --   40.00  85.00   3.07   50
 24  ω     11.00  36.00   0.50    2.00    --   40.00  89.00 -99.97   50
 25  ω     11.00  36.00   0.50    2.00    --   40.00  87.00 141.78   50
 26  ω     10.00  35.00   0.50    2.00    --   40.00  90.00 -57.31   50
 27  ω     11.00  36.00   0.50    2.00    --   40.00  89.00 -78.98   50
 28  ω      9.00  34.00   0.50    2.00    --   40.00  93.00-147.87   50
 29  ω     17.00  42.00   0.50    2.00    --   44.00  83.00-148.67   50
 30  ω     15.00  40.00   0.50    2.00    --   44.00  89.00-134.86   50
 31  ω     15.00  40.00   0.50    2.00    --   44.00  88.00 -96.06   50
 32  ω     14.00  39.00   0.50    2.00    --   44.00  92.00 139.30   50
 33  ω     17.00  42.00   0.50    2.00    --   44.00  83.00 -47.86   50
 34  ω     14.00  39.00   0.50    2.00    --   44.32  92.00  71.29   50
 35  ω     16.00  41.00   0.50    2.00    --   44.32  87.00   2.61   50
 36  ω     83.00 108.00   0.50    2.00    --   44.32  77.00  60.00   50
 37  ω     21.00  52.00   0.50    2.00    --   44.32  77.00  60.00   62
 38  ω     23.00  50.00   0.50    2.00    --   48.00  76.00 -79.87   54
 39  ω    -49.00 -24.00   0.50    2.00    --  -48.00 -72.00  50.87   50
 40  ω     90.00 120.00   0.50    2.00    --   52.00  77.00 -56.07   60
 41  ω    -54.00 -28.00   0.50    2.00    --  -52.00 -73.00-176.65   52
 42  ω    -55.00 -28.00   0.50    2.00    --  -52.00 -73.00 102.57   54
 43  ω     28.00  53.00   0.50    2.00    --   52.00  77.00 -56.07   50
 44  ω   -117.00 -92.00   0.50    2.00    --  -52.00 -73.00-176.65   50
 45  ω   -105.00 -77.00   0.50    2.00    --  -52.00 -73.00 102.57   56
 46  ω    -58.00 -29.00   0.50    2.00    --  -52.00 -70.00 -57.03   58
 47  ω   -121.00 -90.00   0.50    2.00    --  -56.00 -58.00  14.80   62
 48  ω   -121.00 -81.00   0.50    2.00    --  -56.00 -70.00-153.55   80
 49  ω     33.00  83.00   0.50    2.00    --   56.00  76.00 145.95  100
 50  ω    -87.00 -37.00   0.50    2.00    --  -56.00 -58.00  14.80  100
 51  ω    -58.00 -33.00   0.50    2.00    --  -56.00 -70.00-153.55   50
 52  ω   -121.00 -84.00   0.50    2.00    --  -60.00 -76.00 -68.59   74
 53  ω     35.00  62.00   0.50    2.00    --   60.00  77.00 179.02   54
 54  ω    -61.00 -35.00   0.50    2.00    --  -60.00 -76.00 -68.59   52
 55  ω    -75.00 -39.00   0.50    2.00    --  -64.00 -75.00 -76.03   72
 56  ω    -71.00 -41.00   0.50    2.00    --  -64.00 -69.00 -10.36   60
 57  ω    -67.00 -41.00   0.50    2.00    --  -64.00 -70.00 -25.82   52
 58  ω    -67.00 -42.00   0.50    2.00    --  -64.00 -68.00  58.45   50
 59  ω   -129.00-102.00   0.50    2.00    --  -64.00 -68.00  58.45   54
 60  ω    -64.00 -39.00   0.50    2.00    --  -64.00 -77.00 107.44   50
 61  ω    -70.00 -45.00   0.50    2.00    --  -68.00 -73.00  84.28   50
 62  ω   -123.00 -93.00   0.50    2.00    --  -68.00 -73.00  84.28   60
 63  ω    -68.00 -43.00   0.50    2.00    --  -68.00 -76.00 -23.89   50
 64  ω    -69.00 -44.00   0.50    2.00    --  -68.00 -72.00  32.01   50
 65  ω   -123.00 -96.00   0.50    2.00    --  -68.00 -72.00  32.01   54
 66  ω   -134.00 -81.00   0.50    6.20    --  -72.00 -76.00-125.62  106
 67  ω    -75.00 -48.00   0.50    6.20    --  -72.00 -76.00-144.20   54
 68  ω    -73.00 -47.00   0.50    6.20    --  -72.00 -76.00-125.62   52
 69  ω    -74.00 -47.00   0.50    6.20    --  -72.00 -76.00-169.18   54
 70  ω     51.00  80.00   0.50    6.20    --   72.00  76.00  59.95   58
 71  ω    -74.00 -47.00   0.50    6.20    --  -72.00 -76.00 168.48   54
 72  ω    -88.00 -61.00   0.50    6.20    --  -72.00 -66.00  71.70   54
 73  ω    -76.00 -51.00   0.50    6.20    --  -76.00 -77.00-154.44   50
 74  ω   -143.00-118.00   0.50    6.20    --  -76.00 -77.00-154.44   50
 75  ω    -87.00 -51.00   0.50    6.20    --  -76.00 -76.00 156.48   72
 76  ω   -141.00 -94.00   0.50    6.20    --  -76.00 -76.00 156.48   94
 77  ω    -91.00 -52.00   0.50    6.20    --  -76.00 -73.00 -92.06   78
 78  ω    -76.00 -51.00   0.50    6.20    --  -76.00 -75.00 129.24   50
 79  ω   -140.00-113.00   0.50    6.20    --  -76.00 -75.00 129.24   54
 80  ω    -88.00 -58.00   0.50    6.20    --  -80.00 -76.00 151.33   60
 81  ω    -87.00 -60.00   0.50    6.20    --  -80.00 -62.00 -12.97   54
 82  ω    -92.00 -55.00   0.50    6.20    --  -80.00 -75.00 -98.30   74
 83  ω   -136.00-109.00   0.50    6.20    --  -80.00 -75.00 -98.30   54
 84  ω    -87.00 -61.00   0.50    6.20    --  -84.00 -71.00 -64.57   52
 85  ω   -143.00-116.00   0.50    6.20    --  -84.00 -71.00 -64.57   54
 86  ω    -91.00 -59.00   0.50    6.20    --  -84.00 -75.00  48.20   64
 87  ω   -106.00 -62.00   0.50    6.20    --  -84.00 -67.00-148.56   88
 88  ω   -147.00 -94.00   0.50    6.20    --  -84.00 -75.00 117.07  106
 89  ω     61.00  96.00   0.50    6.20    --   84.00  72.00 110.38   70
 90  ω   -117.00 -61.00   0.50    6.20    --  -84.00 -69.00 -23.68  112
 91  ω    -88.00 -61.00   0.50    6.20    --  -84.00 -75.00 117.07   54
 92  ω   -141.00 -65.00   0.50    6.20    --  -88.00 -69.00-178.02  152
 93  ω    -96.00 -63.00   0.50    6.20    --  -88.00 -76.00-114.41   66
 94  ω   -146.00 -63.00   0.50    6.20    --  -88.00 -77.00 -26.97  166
 95  ω   -157.00 -99.00   0.50    6.20    --  -93.31-117.00 -90.00  116
 96  ω    -94.00 -68.00   0.50    6.20    --  -93.31 -77.00 115.03   52
 97  ω   -138.00 -71.00   0.50    6.20    --  -93.31 -72.00 -43.77  134
 98  ω   -122.00 -68.00   0.50    6.20    --  -93.31 -77.00  30.00  108
 99  ω    -54.00 -23.00   0.50    6.20    --  -93.31  96.00 120.00   62
100  ω   -100.00 -70.00   0.50    6.20    --  -93.31 -72.00  18.73   60
101  ω   -104.00 -55.00   0.50    6.20    --  -93.31  96.00 120.00   98
102  ω   -148.00-113.00   0.50    6.20    --  -93.31 -72.00  18.73   70
103  ω   -151.00-115.00   0.50    6.20    --  -93.31 -77.00 115.03   72
104  ω    -90.00 -24.00   0.50    6.20    --  -93.31  96.00 150.00  132
105  ω   -160.00 -70.00   0.50    6.20    --  -93.31 -72.00  79.60  180
106  ω   -104.00 -25.00   0.50    6.20    --  -93.31  96.00 -30.00  158
107  ω   -148.00-121.00   0.50    6.20    --  -93.31 -77.00-150.00   54
108  ω   -123.00 -68.00   0.50    6.20    --  -93.31 -77.00 150.00  110
109  ω    -80.00 -55.00   0.50    6.20    --  -93.31  68.00  90.00   50
110  ω   -159.00-129.00   0.50    6.20    --  -93.31 -77.00 150.00   60
111  ω   -137.00-112.00   0.50    6.20    --  -93.31-133.00  67.00   50
112  ω    -93.00 -68.00   0.50    6.20    --  -93.31 -77.00 -69.15   50
113  ω   -157.00 -68.00   0.50    6.20    --  -93.31 -77.00  60.00  178
114  ω   -146.00 -68.00   0.50    6.20    --  -93.31 -77.00   0.00  156
115  ω   -111.00 -71.00   0.50    6.20    --  -93.31 -77.00-150.00   80
116  ω    -82.00 -34.00   0.50    6.20    --  -93.31  77.00 -60.00   96
117  ω   -139.00-112.00   0.50    6.20    --  -93.31 -77.00 -69.15   54
118  ω     97.00 124.00   0.50    6.20    --   94.87  77.00 -30.00   54
119  ω     71.00 157.00   0.50    6.20    --   94.87  77.00-120.00  172
120  ω    111.00 136.00   0.50    6.20    --   94.87  59.00 -60.00   50
121  ω     80.00 106.00   0.50    6.20    --   94.87  59.00 -60.00   52
122  ω     72.00 159.00   0.50    6.20    --   94.87  77.00  90.00  174
123  ω     70.00  96.00   0.50    6.20    --   94.87  77.00-180.00   52
124  ω     74.00 159.00   0.50    6.20    --   94.87  77.00 -90.00  170
125  ω     91.00 162.00   0.50    6.20    --   94.87  59.00-180.00  142
126  ω     29.00  56.00   0.50    6.20    --   94.87 -50.00 -60.00   54
127  ω     29.00  80.00   0.50    6.20    --   94.87 -68.00 -90.00  102
128  ω     30.00  57.00   0.50    6.20    --   94.87 -68.00-120.00   54
129  ω     96.00 157.00   0.50    6.20    --   94.87  77.00-150.00  122
130  ω     29.00  56.00   0.50    6.20    --   94.87 -50.00  90.00   54
131  ω     29.00  56.00   0.50    6.20    --   94.87 -50.00  60.00   54
132  ω     31.00  56.00   0.50    6.20    --   94.87 -50.00  30.00   50
133  ω     44.00  91.00   0.50    6.20    --   94.87 -77.00   0.00   94
134  ω     71.00 118.00   0.50    6.20    --   94.87  77.00  60.00   94
135  ω    125.00 158.00   0.50    6.20    --   94.87  68.00 120.00   66
136  ω     73.00 106.00   0.50    6.20    --   94.87  68.00 120.00   66
137  ω     40.00  80.00   0.50    6.20    --   94.87 -68.00  60.00   80
138  ω     42.00  67.00   0.50    6.20    --   94.87 -59.00-180.00   50
139  ω    119.00 146.00   0.50    6.20    --   94.87  42.00 150.00   54
140  ω     77.00 104.00   0.50    6.20    --   94.87-117.00 -90.00   54
141  ω    120.00 156.00   0.50    6.20    --   94.87  68.00  60.00   72
142  ω    134.00 159.00   0.50    6.20    --   94.87  68.00  30.00   50
143  ω     40.00  74.00   0.50    6.20    --   94.87-117.00 -90.00   68
144  ω     73.00 100.00   0.50    6.20    --   94.87  68.00  60.00   54
145  ω     76.00 103.00   0.50    6.20    --   94.87  68.00  30.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0057336000
_diffrn_orient_matrix_UB_12      -0.0230787000
_diffrn_orient_matrix_UB_13      -0.1437092000
_diffrn_orient_matrix_UB_21      0.0019713000
_diffrn_orient_matrix_UB_22      0.1083184000
_diffrn_orient_matrix_UB_23      -0.0306487000
_diffrn_orient_matrix_UB_31      0.2069078000
_diffrn_orient_matrix_UB_32      -0.0004975000
_diffrn_orient_matrix_UB_33      0.0131615000
_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  0.0509
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23167
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.642
_diffrn_reflns_theta_min         4.233
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.115a (Rigaku Oxford Diffraction, 2024)
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    1.234
_exptl_crystal_description       prism
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1698 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.17(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3941
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0366
_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/[σ²(Fo²)+(0.0609P)²+0.1170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0952
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                3766
_reflns_number_total             3941
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob02052a2.cif
_cod_data_source_block           Sa5f
_cod_depositor_comments
'Adding full bibliography for 7160364--7160367.cif.'
_cod_database_code               7160366
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H N O '
_chemical_oxdiff_usercomment     'DT B'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.874
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C15(H15),
 C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 1.429
_oxdiff_exptl_absorpt_empirical_full_min 0.661
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8962(3) 0.69729(14) 0.08643(19) 0.0412(5) Uani 1 1 d . . . . .
H1 H 0.871368 0.658856 0.144717 0.062 Uiso 1 1 calc R U . . .
C23 C 0.7375(4) 0.7213(2) 0.0125(3) 0.0406(7) Uani 1 1 d . . . . .
H23A H 0.764336 0.774106 -0.046810 0.049 Uiso 1 1 calc R U . . .
H23B H 0.646988 0.745181 0.070282 0.049 Uiso 1 1 calc R U . . .
C24 C 0.6589(4) 0.6382(2) -0.0638(3) 0.0467(7) Uani 1 1 d . . . . .
H24A H 0.749757 0.611903 -0.118053 0.070 Uiso 1 1 calc R U . . .
H24B H 0.555049 0.660323 -0.117795 0.070 Uiso 1 1 calc R U . . .
H24C H 0.620670 0.588122 -0.005422 0.070 Uiso 1 1 calc R U . . .
N1 N 0.7366(3) 0.46931(13) 0.44106(18) 0.0236(4) Uani 1 1 d . . . . .
N2 N 0.7963(3) 0.56215(15) 0.27238(19) 0.0275(4) Uani 1 1 d . . . . .
N3 N 0.7228(3) 0.64260(15) 0.4615(2) 0.0350(5) Uani 1 1 d . . . . .
N4 N 0.3741(3) 0.52003(15) 0.40222(19) 0.0263(4) Uani 1 1 d . . . . .
C00B C 0.5080(3) 0.45857(16) 0.6079(2) 0.0252(5) Uani 1 1 d . . . . .
C1 C 0.7758(3) 0.40683(18) 0.3420(2) 0.0250(5) Uani 1 1 d . . . . .
C2 C 0.7776(3) 0.30707(18) 0.3350(2) 0.0309(6) Uani 1 1 d . . . . .
H2 H 0.751440 0.267903 0.405943 0.037 Uiso 1 1 calc R U . . .
C3 C 0.8198(4) 0.2678(2) 0.2181(2) 0.0361(6) Uani 1 1 d . . . . .
H3 H 0.822048 0.199912 0.208821 0.043 Uiso 1 1 calc R U . . .
C4 C 0.8588(4) 0.3254(2) 0.1145(3) 0.0364(6) Uani 1 1 d . . . . .
H4 H 0.888415 0.295938 0.036567 0.044 Uiso 1 1 calc R U . . .
C5 C 0.8554(3) 0.42494(19) 0.1227(2) 0.0309(6) Uani 1 1 d . . . . .
H5 H 0.882416 0.463918 0.051880 0.037 Uiso 1 1 calc R U . . .
C6 C 0.8110(3) 0.46599(17) 0.2381(2) 0.0257(5) Uani 1 1 d . . . . .
C7 C 0.7525(3) 0.56123(17) 0.3934(2) 0.0248(5) Uani 1 1 d . . . . .
C8 C 0.7178(5) 0.7322(2) 0.3894(3) 0.0464(8) Uani 1 1 d . . . . .
H8A H 0.839213 0.748196 0.365111 0.070 Uiso 1 1 calc R U . . .
H8B H 0.672910 0.783940 0.442507 0.070 Uiso 1 1 calc R U . . .
H8C H 0.638068 0.724878 0.312115 0.070 Uiso 1 1 calc R U . . .
C9 C 0.7565(4) 0.65265(18) 0.5968(2) 0.0327(6) Uani 1 1 d . . . . .
H9A H 0.790081 0.590092 0.634134 0.049 Uiso 1 1 calc R U . . .
H9B H 0.647875 0.676254 0.634735 0.049 Uiso 1 1 calc R U . . .
H9C H 0.854807 0.698482 0.614277 0.049 Uiso 1 1 calc R U . . .
C10 C 0.6806(3) 0.43656(16) 0.5626(2) 0.0237(5) Uani 1 1 d . . . . .
C11 C 0.8058(3) 0.38488(16) 0.6355(2) 0.0271(5) Uani 1 1 d . . . . .
H11 H 0.917040 0.369188 0.600840 0.033 Uiso 1 1 calc R U . . .
C12 C 0.7736(3) 0.35465(17) 0.7601(2) 0.0295(5) Uani 1 1 d . . . . .
H12 H 0.859363 0.316482 0.807928 0.035 Uiso 1 1 calc R U . . .
C13 C 0.6165(4) 0.38113(17) 0.8114(2) 0.0294(5) Uani 1 1 d . . . . .
H13 H 0.596719 0.364351 0.897439 0.035 Uiso 1 1 calc R U . . .
C14 C 0.4828(3) 0.43304(17) 0.7387(2) 0.0269(5) Uani 1 1 d . . . . .
C15 C 0.3216(3) 0.45994(17) 0.7960(2) 0.0306(5) Uani 1 1 d . . . . .
H15 H 0.304681 0.442976 0.882418 0.037 Uiso 1 1 calc R U . . .
C16 C 0.1920(3) 0.50991(19) 0.7272(3) 0.0317(6) Uani 1 1 d . . . . .
H16 H 0.087338 0.530309 0.767083 0.038 Uiso 1 1 calc R U . . .
C17 C 0.2117(3) 0.53162(17) 0.5975(3) 0.0298(6) Uani 1 1 d . . . . .
H17 H 0.118527 0.565686 0.551052 0.036 Uiso 1 1 calc R U . . .
C18 C 0.3622(3) 0.50495(16) 0.5356(2) 0.0253(5) Uani 1 1 d . . . . .
C19 C 0.2712(4) 0.5988(2) 0.3404(3) 0.0339(6) Uani 1 1 d . . . . .
H19A H 0.314200 0.662118 0.372842 0.041 Uiso 1 1 calc R U . . .
H19B H 0.141315 0.592621 0.353540 0.041 Uiso 1 1 calc R U . . .
C20 C 0.3092(4) 0.5855(2) 0.1999(3) 0.0371(6) Uani 1 1 d . . . . .
H20A H 0.419898 0.620085 0.179293 0.045 Uiso 1 1 calc R U . . .
H20B H 0.207668 0.609350 0.143253 0.045 Uiso 1 1 calc R U . . .
C21 C 0.3326(4) 0.4759(2) 0.1848(2) 0.0351(6) Uani 1 1 d . . . . .
H21A H 0.233481 0.448526 0.128940 0.042 Uiso 1 1 calc R U . . .
H21B H 0.448276 0.460891 0.147401 0.042 Uiso 1 1 calc R U . . .
C22 C 0.3291(3) 0.43575(18) 0.3211(2) 0.0301(5) Uani 1 1 d . . . . .
H22A H 0.208664 0.410337 0.337733 0.036 Uiso 1 1 calc R U . . .
H22B H 0.419137 0.383998 0.335848 0.036 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C23 O1 H1 109.5 . . ?
O1 C23 H23A 108.9 . . ?
O1 C23 H23B 108.9 . . ?
O1 C23 C24 113.3(2) . . ?
H23A C23 H23B 107.7 . . ?
C24 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N1 C10 123.00(18) . . ?
C7 N1 C1 106.35(18) . . ?
C7 N1 C10 130.53(19) . . ?
C7 N2 C6 105.36(19) . . ?
C7 N3 C8 116.1(2) . . ?
C7 N3 C9 125.1(2) . . ?
C9 N3 C8 115.3(2) . . ?
C18 N4 C19 118.9(2) . . ?
C18 N4 C22 115.03(19) . . ?
C19 N4 C22 104.22(19) . . ?
C10 C00B C14 115.8(2) . . ?
C10 C00B C18 126.0(2) . . ?
C14 C00B C18 118.3(2) . . ?
N1 C1 C6 105.5(2) . . ?
C2 C1 N1 131.5(2) . . ?
C2 C1 C6 122.9(2) . . ?
C1 C2 H2 121.9 . . ?
C1 C2 C3 116.1(2) . . ?
C3 C2 H2 121.9 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 121.0 . . ?
C4 C5 C6 118.0(2) . . ?
C6 C5 H5 121.0 . . ?
N2 C6 C1 110.1(2) . . ?
N2 C6 C5 130.1(2) . . ?
C5 C6 C1 119.8(2) . . ?
N2 C7 N1 112.7(2) . . ?
N2 C7 N3 123.3(2) . . ?
N3 C7 N1 124.1(2) . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C00B C10 N1 122.8(2) . . ?
C11 C10 N1 115.7(2) . . ?
C11 C10 C00B 121.5(2) . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.6(2) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.8(2) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C14 121.2(2) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C00B 120.7(2) . . ?
C13 C14 C15 119.5(2) . . ?
C15 C14 C00B 119.9(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.5(2) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.0 . . ?
C18 C17 C16 122.0(2) . . ?
C18 C17 H17 119.0 . . ?
N4 C18 C00B 119.6(2) . . ?
C17 C18 N4 121.5(2) . . ?
C17 C18 C00B 118.9(2) . . ?
N4 C19 H19A 111.3 . . ?
N4 C19 H19B 111.3 . . ?
N4 C19 C20 102.2(2) . . ?
H19A C19 H19B 109.2 . . ?
C20 C19 H19A 111.3 . . ?
C20 C19 H19B 111.3 . . ?
C19 C20 H20A 110.9 . . ?
C19 C20 H20B 110.9 . . ?
C19 C20 C21 104.3(2) . . ?
H20A C20 H20B 108.9 . . ?
C21 C20 H20A 110.9 . . ?
C21 C20 H20B 110.9 . . ?
C20 C21 H21A 110.8 . . ?
C20 C21 H21B 110.8 . . ?
H21A C21 H21B 108.9 . . ?
C22 C21 C20 104.8(2) . . ?
C22 C21 H21A 110.8 . . ?
C22 C21 H21B 110.8 . . ?
N4 C22 C21 103.3(2) . . ?
N4 C22 H22A 111.1 . . ?
N4 C22 H22B 111.1 . . ?
C21 C22 H22A 111.1 . . ?
C21 C22 H22B 111.1 . . ?
H22A C22 H22B 109.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 C23 1.414(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.504(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N1 C1 1.397(3) . ?
N1 C7 1.380(3) . ?
N1 C10 1.436(3) . ?
N2 C6 1.391(3) . ?
N2 C7 1.327(3) . ?
N3 C7 1.363(3) . ?
N3 C8 1.457(3) . ?
N3 C9 1.429(3) . ?
N4 C18 1.419(3) . ?
N4 C19 1.466(3) . ?
N4 C22 1.474(3) . ?
C00B C10 1.431(3) . ?
C00B C14 1.437(3) . ?
C00B C18 1.440(3) . ?
C1 C2 1.390(4) . ?
C1 C6 1.401(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.373(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.404(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.368(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.415(4) . ?
C14 C15 1.425(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.361(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.407(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.379(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.525(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.544(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.534(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
