#------------------------------------------------------------------------------
#$Date: 2022-07-27 00:55:19 +0300 (Wed, 27 Jul 2022) $
#$Revision: 276944 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/04/7130412.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_7130412
loop_
_publ_author_name
'Abeysekera, Amila M.'
'Averkiev, Boris B.'
'Sinha, Abhijeet Shekhar'
'Aakeröy, Christer'
_publ_section_title
;
 Evaluating structure-property relationship in a new family of
 mechanically flexible co-crystals
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02047E
_journal_year                    2022
_chemical_formula_moiety         'C8 H9 I N2 O, C9 H10 O2'
_chemical_formula_sum            'C17 H19 I N2 O3'
_chemical_formula_weight         426.24
_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             2021-06-23
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2022-02-14 deposited with the CCDC.	2022-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                97.439(2)
_cell_angle_beta                 94.401(3)
_cell_angle_gamma                93.065(3)
_cell_formula_units_Z            2
_cell_length_a                   4.5288(2)
_cell_length_b                   12.8682(4)
_cell_length_c                   15.2840(4)
_cell_measurement_reflns_used    15005
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      76.7210
_cell_measurement_theta_min      2.9380
_cell_volume                     878.80(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  -5.00   0.50    1.80    --  -43.05 112.00  19.00  148
  2  ω     25.00  86.00   0.50    1.80    --   43.05-112.00 -72.00  122
  3  ω   -128.00-100.00   0.50    7.40    --  -90.25-112.00 -72.00   56
  4  ω    -70.00 -43.00   0.50    7.40    --  -90.25 112.00  19.00   54
  5  ω     82.00 107.00   0.50    7.40    --  111.75-112.00 -72.00   50
  6  ω    108.00 164.00   0.50    7.40    --  111.75 112.00  19.00  112
  7  ω    -63.00  28.00   0.50    1.80    --  -43.05  57.00 -60.00  182
  8  ω    -52.00 -14.00   0.50    1.80    --  -43.05 -77.00-150.00   76
  9  ω    -51.00 -20.00   0.50    1.80    --  -43.05 -38.00-150.00   62
 10  ω    -62.00 -14.00   0.50    1.80    --  -43.05 -77.00  90.00   96
 11  ω   -120.00 -73.00   0.50    1.80    --  -43.05 -38.00   0.00   94
 12  ω    -68.00 -20.00   0.50    1.80    --  -43.05 -38.00   0.00   96
 13  ω    -66.00 -20.00   0.50    1.80    --  -43.05 -57.00 -90.00   92
 14  ω     83.00 114.00   0.50    1.80    --   43.05  57.00-120.00   62
 15  ω     38.00  95.00   0.50    1.80    --   43.05-125.00  30.00  114
 16  ω     25.00  62.00   0.50    1.80    --   43.05  38.00  60.00   74
 17  ω     29.00  59.00   0.50    1.80    --   43.05  57.00-120.00   60
 18  ω     82.00 110.00   0.50    1.80    --   43.05  57.00  90.00   56
 19  ω     23.00  49.00   0.50    1.80    --   43.05  57.00  90.00   52
 20  ω     15.00  43.00   0.50    1.80    --   46.00  87.00 -53.97   56
 21  ω     14.00  39.00   0.50    1.80    --   46.00  85.00-102.22   50
 22  ω     17.00  42.00   0.50    1.80    --   50.00  87.00  39.44   50
 23  ω     16.00  43.00   0.50    1.80    --   50.00  90.00 129.80   54
 24  ω     17.00  42.00   0.50    1.80    --   50.00  87.00  82.02   50
 25  ω     17.00  42.00   0.50    1.80    --   50.00  86.00-140.93   50
 26  ω   -120.00 -93.00   0.50    1.80    --  -54.00 -76.00  57.11   54
 27  ω    -66.00 -25.00   0.50    1.80    --  -54.00 -76.00  57.11   82
 28  ω    -90.00 -34.00   0.50    1.80    --  -58.00 -67.00-155.28  112
 29  ω     32.00  86.00   0.50    1.80    --   58.00  76.00  -6.61  108
 30  ω    -67.00 -39.00   0.50    1.80    --  -62.00 -63.00-141.26   56
 31  ω     34.00  61.00   0.50    1.80    --   62.00  75.00 148.80   54
 32  ω    100.00 125.00   0.50    1.80    --   62.00  75.00 148.80   50
 33  ω    -65.00 -37.00   0.50    1.80    --  -66.00 -76.00 -74.21   56
 34  ω    -95.00 -46.00   0.50    1.80    --  -66.00 -55.00 122.55   98
 35  ω    -75.00 -45.00   0.50    1.80    --  -66.00 -60.00 145.26   60
 36  ω    -74.00 -46.00   0.50    1.80    --  -66.00 -59.00-126.80   56
 37  ω   -111.00 -83.00   0.50    1.80    --  -66.00 -65.00-177.16   56
 38  ω    -78.00 -43.00   0.50    1.80    --  -66.00 -65.00-177.16   70
 39  ω    -73.00 -45.00   0.50    7.40    --  -70.00 -67.00  86.78   56
 40  ω    -67.00 -42.00   0.50    7.40    --  -70.00 -75.00-138.16   50
 41  ω    -74.00 -47.00   0.50    7.40    --  -70.00 -63.00 162.05   54
 42  ω   -138.00-110.00   0.50    7.40    --  -70.00 -67.00  86.78   56
 43  ω    -94.00 -62.00   0.50    7.40    --  -74.00 -54.00  58.54   64
 44  ω    -74.00 -46.00   0.50    7.40    --  -74.00 -74.00 -75.85   56
 45  ω    -79.00 -51.00   0.50    7.40    --  -74.00 -62.00 -62.50   56
 46  ω    -78.00 -50.00   0.50    7.40    --  -74.00 -61.00-141.34   56
 47  ω    -72.00 -47.00   0.50    7.40    --  -74.00 -73.00 113.57   50
 48  ω   -112.00 -84.00   0.50    7.40    --  -74.00 -58.00 -52.85   56
 49  ω    -81.00 -53.00   0.50    7.40    --  -74.00 -58.00 -52.85   56
 50  ω    -78.00 -51.00   0.50    7.40    --  -78.00 -72.00-158.59   54
 51  ω    -79.00 -54.00   0.50    7.40    --  -82.00 -74.00  43.24   50
 52  ω   -148.00-119.00   0.50    7.40    --  -82.00 -74.00  43.24   58
 53  ω    -82.00 -54.00   0.50    7.40    --  -82.00 -74.00 -75.68   56
 54  ω    -82.00 -54.00   0.50    7.40    --  -82.00 -75.00 131.65   56
 55  ω    -81.00 -53.00   0.50    7.40    --  -82.00 -76.00   5.80   56
 56  ω    -80.00 -55.00   0.50    7.40    --  -82.00 -71.00  21.41   50
 57  ω   -160.00-133.00   0.50    7.40    --  -86.00 -73.00   3.05   54
 58  ω    -87.00 -60.00   0.50    7.40    --  -86.00 -73.00   3.05   54
 59  ω    -90.00 -63.00   0.50    7.40    --  -90.00 -71.00 161.19   54
 60  ω    -89.00 -61.00   0.50    7.40    --  -90.25 -77.00 -30.00   56
 61  ω    -89.00 -61.00   0.50    7.40    --  -90.25 -77.00-180.00   56
 62  ω   -159.00-131.00   0.50    7.40    --  -90.25 -77.00 -30.00   56
 63  ω    -90.00 -65.00   0.50    7.40    --  -90.25 -68.00 -54.36   50
 64  ω    -87.00 -62.00   0.50    7.40    --  -90.25 -75.00  66.30   50
 65  ω    -89.00 -61.00   0.50    7.40    --  -90.25 -77.00  30.00   56
 66  ω   -114.00 -63.00   0.50    7.40    --  -90.25 -77.00 120.00  102
 67  ω    -90.00 -63.00   0.50    7.40    --  -90.25 -73.00-174.33   54
 68  ω    -88.00 -61.00   0.50    7.40    --  -90.25 -77.00 -60.00   54
 69  ω    -89.00 -62.00   0.50    7.40    --  -90.25 -74.00 127.72   54
 70  ω    -88.00 -61.00   0.50    7.40    --  -90.25 -77.00-120.00   54
 71  ω    -91.00 -64.00   0.50    7.40    --  -90.25 -71.00  42.63   54
 72  ω    -86.00 -61.00   0.50    7.40    --  -90.25 -77.00   0.00   50
 73  ω    -91.00 -63.00   0.50    7.40    --  -90.25 -72.00  -0.09   56
 74  ω    -87.00 -62.00   0.50    7.40    --  -90.25 -76.00 -85.25   50
 75  ω   -147.00-121.00   0.50    7.40    --  -90.25 -72.00  -0.09   52
 76  ω    -90.00 -63.00   0.50    7.40    --  -90.25 -73.00-143.56   54
 77  ω     35.00 108.00   0.50    7.40    --  110.00-112.00  28.88  146
 78  ω    139.00 178.00   0.50    7.40    --  111.75  77.00 -60.00   78
 79  ω     84.00 125.00   0.50    7.40    --  111.75  77.00 -60.00   82
 80  ω    115.00 159.00   0.50    7.40    --  111.75 125.00  90.00   88
 81  ω    120.00 159.00   0.50    7.40    --  111.75 125.00 -60.00   78
 82  ω     41.00  84.00   0.50    7.40    --  111.75-125.00 -30.00   86
 83  ω     83.00 115.00   0.50    7.40    --  111.75  77.00-150.00   64
 84  ω     85.00 175.00   0.50    7.40    --  111.75  77.00   0.00  180
 85  ω     73.00 100.00   0.50    7.40    --  111.75 -94.00-150.00   54
 86  ω     88.00 173.00   0.50    7.40    --  111.75  61.00 120.00  170
 87  ω     41.00  68.00   0.50    7.40    --  111.75 -94.00-150.00   54
 88  ω     42.00  71.00   0.50    7.40    --  111.75 -61.00  30.00   58
 89  ω     88.00 173.00   0.50    7.40    --  111.75  61.00-120.00  170
 90  ω     89.00 147.00   0.50    7.40    --  111.75  61.00 -90.00  116
 91  ω     78.00 105.00   0.50    7.40    --  111.75 -77.00 150.00   54
 92  ω     93.00 125.00   0.50    7.40    --  111.75  45.00  60.00   64
 93  ω     42.00 105.00   0.50    7.40    --  111.75-125.00   0.00  126
 94  ω     71.00 104.00   0.50    7.40    --  111.75 -77.00-120.00   66
 95  ω     90.00 167.00   0.50    7.40    --  111.75  61.00 -60.00  154
 96  ω     44.00  78.00   0.50    7.40    --  111.75-114.00  41.78   68
 97  ω    121.00 174.00   0.50    7.40    --  111.75  77.00  30.00  106
 98  ω     88.00 116.00   0.50    7.40    --  111.75  77.00  30.00   56
 99  ω     55.00 106.00   0.50    7.40    --  111.75 -94.00  60.00  102
100  ω    130.00 178.00   0.50    7.40    --  111.75  77.00 -90.00   96
101  ω     85.00 115.00   0.50    7.40    --  111.75  77.00 -90.00   60
102  ω     80.00 106.00   0.50    7.40    --  111.75 -94.00 -60.00   52
103  ω    130.00 162.00   0.50    7.40    --  111.75  61.00 -30.00   64
104  ω     43.00  69.00   0.50    7.40    --  111.75 -61.00 -90.00   52
105  ω    131.00 158.00   0.50    7.40    --  111.75  15.00   0.00   54
106  ω     40.00  67.00   0.50    7.40    --  111.75 -94.00 -60.00   54
107  ω     38.00  63.00   0.50    7.40    --  111.75 -61.00 -30.00   50
108  ω     44.00  69.00   0.50    7.40    --  111.75 -61.00   0.00   50
109  ω     87.00 112.00   0.50    7.40    --  111.75  15.00   0.00   50
110  ω     89.00 175.00   0.50    7.40    --  111.75  61.00-150.00  172
111  ω     39.00  99.00   0.50    7.40    --  111.75 -77.00  90.00  120
112  ω     38.00  75.00   0.50    7.40    --  111.75 -77.00 150.00   74
113  ω    129.00 157.00   0.50    7.40    --  111.75  15.00-180.00   56
114  ω     85.00 135.00   0.50    7.40    --  111.75  77.00-120.00  100
115  ω     90.00 123.00   0.50    7.40    --  111.75  61.00 -30.00   66
116  ω     62.00 108.00   0.50    7.40    --  111.75  15.00-180.00   92
117  ω    121.00 148.00   0.50    7.40    --  111.75-177.00 178.98   54
118  ω     66.00 105.00   0.50    7.40    --  111.75-177.00 178.98   78
119  ω    153.00 178.00   0.50    7.40    --  111.75  61.00-180.00   50
120  ω     91.00 139.00   0.50    7.40    --  111.75  61.00 150.00   96
121  ω     65.00 106.00   0.50    7.40    --  111.75 -94.00  90.00   82
122  ω     43.00  68.00   0.50    7.40    --  111.75 -61.00-120.00   50
123  ω     83.00 157.00   0.50    7.40    --  111.75  77.00  60.00  148
124  ω     92.00 133.00   0.50    7.40    --  111.75  61.00-180.00   82
125  ω     85.00 174.00   0.50    7.40    --  111.75  71.00  81.25  178
126  ω    140.00 177.00   0.50    7.40    --  111.75  77.00 -30.00   74
127  ω     85.00 112.00   0.50    7.40    --  111.75  77.00 -30.00   54
128  ω    124.00 170.00   0.50    7.40    --  111.75  45.00-180.00   92
129  ω     92.00 136.00   0.50    7.40    --  111.75  45.00   0.00   88
130  ω     41.00 100.00   0.50    7.40    --  111.75 -94.00-120.00  118
131  ω    117.00 175.00   0.50    7.40    --  111.75  77.00 150.00  116
132  ω    139.00 166.00   0.50    7.40    --  111.75  77.00-180.00   54
133  ω     88.00 134.00   0.50    7.40    --  111.75  77.00-180.00   92
134  ω     83.00 113.00   0.50    7.40    --  111.75  77.00 150.00   60
135  ω    129.00 156.00   0.50    7.40    --  111.75  77.00  90.00   54
136  ω     98.00 126.00   0.50    7.40    --  111.75  45.00 150.00   56
137  ω     86.00 113.00   0.50    7.40    --  111.75  77.00  90.00   54
138  ω     89.00 155.00   0.50    7.40    --  111.75  61.00  60.00  132
139  ω     82.00 112.00   0.50    7.40    --  111.75-125.00 -90.00   60
140  ω    118.00 148.00   0.50    7.40    --  111.75 125.00-120.00   60
141  ω     79.00 111.00   0.50    7.40    --  111.75-125.00-150.00   64
142  ω    142.00 168.00   0.50    7.40    --  111.75  61.00  30.00   52
143  ω     61.00 102.00   0.50    7.40    --  111.75 -94.00 120.00   82
144  ω     72.00  97.00   0.50    7.40    --  111.75 -77.00 -60.00   50
145  ω     96.00 160.00   0.50    7.40    --  111.75  61.00   0.00  128
146  ω     88.00 115.00   0.50    7.40    --  111.75  61.00  30.00   54
147  ω     41.00  66.00   0.50    7.40    --  111.75-125.00 -90.00   50
148  ω     42.00  95.00   0.50    7.40    --  111.75 -77.00  30.00  106
149  ω     38.00  63.00   0.50    7.40    --  111.75 -61.00 120.00   50
150  ω    126.00 172.00   0.50    7.40    --  111.75  77.00-150.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0920977000
_diffrn_orient_matrix_UB_12      0.0278304000
_diffrn_orient_matrix_UB_13      -0.0895335000
_diffrn_orient_matrix_UB_21      0.1146551000
_diffrn_orient_matrix_UB_22      0.1104642000
_diffrn_orient_matrix_UB_23      0.0447875000
_diffrn_orient_matrix_UB_31      0.3086289000
_diffrn_orient_matrix_UB_32      -0.0407468000
_diffrn_orient_matrix_UB_33      0.0196271000
_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  0.0500
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24138
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.029
_diffrn_reflns_theta_min         2.926
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    14.451
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.111a (Rigaku Oxford Diffraction, 2021)
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    1.611
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_recrystallization_method 'crystallized from ethylacetate'
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.059
_refine_diff_density_max         0.954
_refine_diff_density_min         -1.052
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       0.0012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0391
_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/[σ²(Fo²)+(0.0555P)²+1.3675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1082
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3224
_reflns_number_total             3664
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc02047e2.cif
_cod_data_source_block           I-Et_35M-BA
_cod_database_code               7130412
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C17H19IN2O3
_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   0.483
_shelx_estimated_absorpt_t_min   0.213
_reflns_odcompleteness_completeness 92.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     83.67
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(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:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N8(H8), C14(H14), C3(H3), C5(H5), C18(H18), C6(H6), C16(H16)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C22(H22A,H22B,H22C), C12(H12A,H12B,H12C)
2.d Idealised tetrahedral OH refined as rotating group:
 O21(H21)
;
_olex2_date_sample_data_collection 2021-06-22
_olex2_date_sample_submission    2021-06-22
_olex2_exptl_crystal_mounting_method 'mounted on a MiTeGen loop'
_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 3.314
_oxdiff_exptl_absorpt_empirical_full_min 0.628
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
I7 I -0.42527(7) 0.05471(2) 0.37867(2) 0.05303(14) Uani 1 1 d . . . . .
O21 O 0.4839(7) 0.2011(2) 0.7056(2) 0.0504(7) Uani 1 1 d . . . . .
H21 H 0.352984 0.225797 0.673746 0.076 Uiso 1 1 calc R U . . .
O20 O 0.5592(7) 0.3689(2) 0.7664(2) 0.0543(8) Uani 1 1 d . . . . .
O10 O -0.2238(8) 0.5642(3) 0.6346(2) 0.0586(8) Uani 1 1 d . . . . .
N2 N 0.0648(8) 0.2600(3) 0.5911(2) 0.0424(7) Uani 1 1 d . . . . .
N8 N 0.0897(8) 0.4333(3) 0.6495(2) 0.0441(8) Uani 1 1 d . . . . .
H8 H 0.255296 0.419178 0.678335 0.053 Uiso 1 1 calc R U . . .
C1 C -0.0399(9) 0.3547(3) 0.5853(3) 0.0410(8) Uani 1 1 d . . . . .
C9 C -0.0125(10) 0.5313(3) 0.6732(3) 0.0452(9) Uani 1 1 d . . . . .
C4 C -0.2634(9) 0.1875(3) 0.4664(3) 0.0435(9) Uani 1 1 d . . . . .
C14 C 0.9805(10) 0.3145(3) 0.8958(3) 0.0458(9) Uani 1 1 d . . . . .
H14 H 0.939178 0.386403 0.897990 0.055 Uiso 1 1 calc R U . . .
C13 C 0.8359(9) 0.2410(3) 0.8293(3) 0.0415(9) Uani 1 1 d . . . . .
C17 C 1.1027(10) 0.1037(4) 0.8881(3) 0.0486(10) Uani 1 1 d . . . . .
C19 C 0.6130(10) 0.2766(3) 0.7644(3) 0.0450(9) Uani 1 1 d . . . . .
C3 C -0.0454(10) 0.1786(3) 0.5325(3) 0.0439(9) Uani 1 1 d . . . . .
H3 H 0.029696 0.111711 0.536583 0.053 Uiso 1 1 calc R U . . .
C5 C -0.3726(10) 0.2861(4) 0.4605(3) 0.0475(10) Uani 1 1 d . . . . .
H5 H -0.523364 0.294520 0.415659 0.057 Uiso 1 1 calc R U . . .
C18 C 0.8985(10) 0.1356(4) 0.8257(3) 0.0478(10) Uani 1 1 d . . . . .
H18 H 0.800979 0.085137 0.780366 0.057 Uiso 1 1 calc R U . . .
C15 C 1.1833(10) 0.2846(4) 0.9587(3) 0.0492(10) Uani 1 1 d . . . . .
C6 C -0.2608(10) 0.3698(3) 0.5194(3) 0.0476(10) Uani 1 1 d . . . . .
H6 H -0.331238 0.437490 0.516065 0.057 Uiso 1 1 calc R U . . .
C16 C 1.2409(10) 0.1785(4) 0.9537(3) 0.0509(10) Uani 1 1 d . . . . .
H16 H 1.379290 0.157099 0.996656 0.061 Uiso 1 1 calc R U . . .
C11 C 0.1568(12) 0.5907(4) 0.7542(4) 0.0580(12) Uani 1 1 d . . . . .
H11A H 0.371965 0.586949 0.747793 0.070 Uiso 1 1 calc R U . . .
H11B H 0.111023 0.556351 0.806379 0.070 Uiso 1 1 calc R U . . .
C23 C 1.1718(14) -0.0105(4) 0.8830(4) 0.0678(14) Uani 1 1 d . . . . .
H23A H 1.127573 -0.036709 0.938299 0.102 Uiso 1 1 calc R U . . .
H23B H 1.382300 -0.017175 0.874168 0.102 Uiso 1 1 calc R U . . .
H23C H 1.050190 -0.051569 0.833316 0.102 Uiso 1 1 calc R U . . .
C22 C 1.3418(13) 0.3640(5) 1.0302(4) 0.0665(13) Uani 1 1 d . . . . .
H22A H 1.553309 0.370218 1.020780 0.100 Uiso 1 1 calc R U . . .
H22B H 1.317861 0.341198 1.088119 0.100 Uiso 1 1 calc R U . . .
H22C H 1.257451 0.432312 1.028232 0.100 Uiso 1 1 calc R U . . .
C12 C 0.0858(15) 0.7054(4) 0.7709(4) 0.0667(14) Uani 1 1 d . . . . .
H12A H 0.143065 0.741228 0.721337 0.100 Uiso 1 1 calc R U . . .
H12B H 0.196078 0.739121 0.825809 0.100 Uiso 1 1 calc R U . . .
H12C H -0.127587 0.709913 0.776224 0.100 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'
I I -0.3257 6.8362 '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
C3 N2 C1 118.8(4) . . ?
C9 N8 C1 127.1(4) . . ?
N2 C1 N8 113.8(4) . . ?
N2 C1 C6 121.6(4) . . ?
N8 C1 C6 124.6(4) . . ?
O10 C9 N8 123.5(4) . . ?
O10 C9 C11 123.5(4) . . ?
N8 C9 C11 113.0(4) . . ?
C3 C4 I7 119.9(3) . . ?
C3 C4 C5 118.4(4) . . ?
C5 C4 I7 121.7(3) . . ?
C15 C14 C13 121.0(4) . . ?
C14 C13 C19 119.1(4) . . ?
C14 C13 C18 119.4(4) . . ?
C18 C13 C19 121.5(4) . . ?
C18 C17 C23 120.1(5) . . ?
C16 C17 C18 118.7(4) . . ?
C16 C17 C23 121.2(4) . . ?
O21 C19 C13 114.5(4) . . ?
O20 C19 O21 123.6(4) . . ?
O20 C19 C13 121.9(4) . . ?
N2 C3 C4 122.8(4) . . ?
C6 C5 C4 119.3(4) . . ?
C17 C18 C13 120.5(4) . . ?
C14 C15 C16 118.3(4) . . ?
C14 C15 C22 121.2(4) . . ?
C16 C15 C22 120.5(4) . . ?
C5 C6 C1 119.0(4) . . ?
C17 C16 C15 122.0(4) . . ?
C9 C11 C12 113.3(4) . . ?
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
I7 C4 2.092(4) . ?
O21 C19 1.313(5) . ?
O20 C19 1.222(5) . ?
O10 C9 1.211(5) . ?
N2 C1 1.342(5) . ?
N2 C3 1.334(5) . ?
N8 C1 1.387(6) . ?
N8 C9 1.380(5) . ?
C1 C6 1.403(6) . ?
C9 C11 1.501(7) . ?
C4 C3 1.377(6) . ?
C4 C5 1.397(6) . ?
C14 C13 1.393(6) . ?
C14 C15 1.384(6) . ?
C13 C19 1.493(6) . ?
C13 C18 1.396(6) . ?
C17 C18 1.392(6) . ?
C17 C16 1.383(7) . ?
C17 C23 1.512(7) . ?
C5 C6 1.360(7) . ?
C15 C16 1.396(7) . ?
C15 C22 1.506(7) . ?
C11 C12 1.522(7) . ?
