# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_in_2022_281
_database_code_depnum_ccdc_archive 'CCDC 2285266'
loop_
_audit_author_name
_audit_author_address
'Ivan Nemec'
;Faculty of Science, Palacky University in Olomouc
Czech Republic
;
_audit_update_record             
;
2023-07-28 deposited with the CCDC.	2024-07-04 downloaded from the CCDC.
;
_audit_creation_date             2023-04-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 Cl N3'
_chemical_formula_sum            'C20 H12 Cl N3'
_chemical_formula_weight         329.78
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
Cl Cl 0.3639 0.7018 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.66903(6)
_cell_length_b                   13.58537(6)
_cell_length_c                   11.39283(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.8862(5)
_cell_angle_gamma                90
_cell_volume                     1609.720(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    34204
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      69.6000
_cell_measurement_theta_min      3.9380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 2 1 0.1073
-2 -2 -1 0.1098
2 -1 -2 0.0940
-2 1 2 0.0940
-2 -1 -2 0.1161
-1 2 1 0.1313
2 -1 0 0.1475
-2 1 0 0.1125
-1 1 0 0.1205
1 -2 0 0.1599
-1 2 0 0.1250
-1 2 -1 0.1138
1 -2 1 0.1676
-1 -2 0 0.1265
1 2 0 0.1253
1 2 -1 0.1130
2 -1 2 0.1692
2 2 -1 0.1027
-2 -2 1 0.1095
0 -1 2 0.1453
0 1 -2 0.0875
1 1 -1 0.0946
0 -1 -1 0.1054
1 -1 -1 0.1043
-1 0 0 0.1003
1 0 0 0.1258
-1 0 2 0.0858
1 0 -2 0.0802
-1 -1 2 0.1064
1 0 2 0.1551
1 -1 -2 0.0728
1 0 -1 0.0763

_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.166
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00 -53.00   0.50    0.20    --  -42.75 114.00 124.00   52
  2  ω    -78.00 -47.00   0.50    0.20    --  -42.75-172.00-107.00   62
  3  ω   -115.00 -71.00   0.50    0.20    --  -42.75 172.00 -94.00   88
  4  ω     64.00  90.00   0.50    0.20    --   44.32-172.00-107.00   52
  5  ω     60.00  85.00   0.50    0.20    --   44.32 172.00 -94.00   50
  6  ω     16.00  83.00   0.50    0.20    --   44.32-114.00  33.00  134
  7  ω   -109.00 -83.00   0.50    0.50    --  -95.95 114.00 124.00   52
  8  ω    -82.00 -47.00   0.50    0.50    --  -95.95 172.00 -94.00   70
  9  ω   -131.00-105.00   0.50    0.50    --  -95.95 172.00 -94.00   52
 10  ω   -161.00-115.00   0.50    0.50    --  -95.95-114.00  33.00   92
 11  ω     73.00  98.00   0.50    0.50    --   97.51 172.00 -94.00   50
 12  ω     97.00 122.00   0.50    0.50    --   97.51 114.00 124.00   50
 13  ω     66.00 105.00   0.50    0.50    --   97.51-114.00  33.00   78
 14  ω    -54.00  -9.00   0.50    0.20    --  -10.00 119.00-122.45   90
 15  ω    -23.00   2.00   0.50    0.20    --   14.00 105.00  47.90   50
 16  ω    -54.00  -2.00   0.50    0.20    --  -14.00 111.00 159.44  104
 17  ω    -56.00 -31.00   0.50    0.20    --   14.00 159.00-133.33   50
 18  ω     -4.00  21.00   0.50    0.20    --   30.00 100.00-103.63   50
 19  ω     -4.00  21.00   0.50    0.20    --   30.00 100.00  31.34   50
 20  ω     -3.00  22.00   0.50    0.20    --   30.00  99.00  69.92   50
 21  ω     -2.00  23.00   0.50    0.20    --   30.00  96.00 168.98   50
 22  ω      2.00  27.00   0.50    0.20    --   34.00  97.00 -28.31   50
 23  ω      6.00  31.00   0.50    0.20    --   38.00  95.00 108.93   50
 24  ω      6.00  31.00   0.50    0.20    --   38.00  95.00 173.64   50
 25  ω      6.00  31.00   0.50    0.20    --   38.00  95.00  30.83   50
 26  ω      7.00  32.00   0.50    0.20    --   38.00  94.00 -68.01   50
 27  ω      6.00  31.00   0.50    0.20    --   38.00  95.00-156.52   50
 28  ω     12.00  37.00   0.50    0.20    --   42.00  90.00  -9.82   50
 29  ω     14.00  39.00   0.50    0.20    --   42.00  91.00 114.62   50
 30  ω     12.00  37.00   0.50    0.20    --   42.00  90.00-118.80   50
 31  ω    -42.00 -17.00   0.50    0.20    --  -42.75 -91.00-159.99   50
 32  ω     16.00  41.00   0.50    0.20    --   46.00  91.00-178.16   50
 33  ω     16.00  41.00   0.50    0.20    --   46.00  92.00  92.21   50
 34  ω     17.00  42.00   0.50    0.20    --   46.00  87.00 -86.15   50
 35  ω     16.00  41.00   0.50    0.20    --   46.00  92.00 159.44   50
 36  ω     16.00  41.00   0.50    0.20    --   46.00  91.00  24.51   50
 37  ω     17.00  42.00   0.50    0.20    --   46.00  88.00 -49.99   50
 38  ω     16.00  41.00   0.50    0.20    --   46.00  91.00  69.74   50
 39  ω     16.00  41.00   0.50    0.20    --   46.00  90.00   9.93   50
 40  ω    -76.00 -31.00   0.50    0.20    --  -54.00 -71.00 129.27   90
 41  ω   -119.00 -93.00   0.50    0.20    --  -54.00 -73.00 163.41   52
 42  ω    -64.00 -33.00   0.50    0.20    --  -54.00 -70.00-171.46   62
 43  ω     66.00  92.00   0.50    0.20    --   54.00  77.00  31.54   52
 44  ω     30.00  56.00   0.50    0.20    --   54.00  77.00  31.54   52
 45  ω    -55.00 -30.00   0.50    0.20    --  -54.00 -73.00 163.41   50
 46  ω    -55.00 -29.00   0.50    0.20    --  -54.00 -76.00  39.39   52
 47  ω    -57.00 -31.00   0.50    0.20    --  -54.00 -72.00  -5.54   52
 48  ω   -113.00 -72.00   0.50    0.20    --  -54.00 -74.00 -84.88   82
 49  ω   -110.00 -84.00   0.50    0.20    --  -54.00 -76.00  39.39   52
 50  ω    -58.00 -30.00   0.50    0.20    --  -54.00 -74.00 -84.88   56
 51  ω    -71.00 -33.00   0.50    0.20    --  -58.00 -76.00  84.09   76
 52  ω     39.00  65.00   0.50    0.20    --   58.00  75.00 -25.03   52
 53  ω    -63.00 -37.00   0.50    0.20    --  -58.00 -71.00-121.70   52
 54  ω     33.00  97.00   0.50    0.20    --   58.00  77.00 173.89  128
 55  ω    -70.00 -40.00   0.50    0.20    --  -62.00 -69.00-143.80   60
 56  ω    -64.00 -39.00   0.50    0.20    --  -62.00 -69.00  17.23   50
 57  ω    -64.00 -39.00   0.50    0.20    --  -62.00 -70.00 -98.09   50
 58  ω   -102.00 -70.00   0.50    0.20    --  -62.00 -69.00  17.23   64
 59  ω    -63.00 -37.00   0.50    0.20    --  -62.00 -76.00  58.75   52
 60  ω    -68.00 -39.00   0.50    0.20    --  -62.00 -72.00  -9.58   58
 61  ω    -70.00 -41.00   0.50    0.20    --  -66.00 -75.00  42.55   58
 62  ω   -128.00 -43.00   0.50    0.20    --  -66.00 -69.00 129.82  170
 63  ω    -73.00 -41.00   0.50    0.20    --  -66.00 -76.00 -25.32   64
 64  ω    -78.00 -45.00   0.50    0.50    --  -70.00 -77.00-157.02   66
 65  ω   -107.00 -45.00   0.50    0.50    --  -70.00 -76.00 -35.79  124
 66  ω   -123.00 -97.00   0.50    0.50    --  -74.00 -76.00 -82.66   52
 67  ω    -75.00 -49.00   0.50    0.50    --  -74.00 -76.00 -82.66   52
 68  ω    -82.00 -51.00   0.50    0.50    --  -74.00 -72.00 -70.31   62
 69  ω    -81.00 -50.00   0.50    0.50    --  -74.00 -74.00-175.47   62
 70  ω    -82.00 -49.00   0.50    0.50    --  -74.00 -76.00-101.65   66
 71  ω   -140.00 -91.00   0.50    0.50    --  -74.00 -76.00-101.65   98
 72  ω    -79.00 -54.00   0.50    0.50    --  -78.00 -72.00  21.90   50
 73  ω    -90.00 -54.00   0.50    0.50    --  -78.00 -74.00 128.31   72
 74  ω    -94.00 -53.00   0.50    0.50    --  -78.00 -77.00 175.30   82
 75  ω    -78.00 -53.00   0.50    0.50    --  -78.00 -76.00 100.70   50
 76  ω    -87.00 -53.00   0.50    0.50    --  -78.00 -75.00-119.07   68
 77  ω   -133.00 -85.00   0.50    0.50    --  -78.00 -72.00  21.90   96
 78  ω    -90.00 -55.00   0.50    0.50    --  -78.00 -77.00  81.75   70
 79  ω   -123.00 -97.00   0.50    0.50    --  -78.00 -77.00  81.75   52
 80  ω    -87.00 -57.00   0.50    0.50    --  -82.00 -77.00 115.13   60
 81  ω    -92.00 -57.00   0.50    0.50    --  -82.00 -77.00 -96.20   70
 82  ω    -84.00 -59.00   0.50    0.50    --  -82.00 -75.00   8.88   50
 83  ω    -99.00 -57.00   0.50    0.50    --  -82.00 -76.00  49.70   84
 84  ω   -144.00 -58.00   0.50    0.50    --  -82.00 -74.00-133.39  172
 85  ω   -146.00-100.00   0.50    0.50    --  -82.00 -77.00 -17.89   92
 86  ω    -94.00 -57.00   0.50    0.50    --  -82.00 -77.00 -17.89   74
 87  ω    -86.00 -57.00   0.50    0.50    --  -82.00 -76.00 -43.07   58
 88  ω   -109.00 -64.00   0.50    0.50    --  -86.00 -71.00 -64.41   90
 89  ω    -92.00 -66.00   0.50    0.50    --  -86.00 -70.00 129.88   52
 90  ω   -152.00-115.00   0.50    0.50    --  -86.00 -71.00 -64.41   74
 91  ω   -145.00 -63.00   0.50    0.50    --  -86.00 -77.00-173.47  164
 92  ω   -153.00-127.00   0.50    0.50    --  -90.00 -76.00  38.14   52
 93  ω   -149.00 -70.00   0.50    0.50    --  -90.00 -59.00 105.08  158
 94  ω   -106.00 -65.00   0.50    0.50    --  -90.00 -76.00  38.14   82
 95  ω    -90.00 -65.00   0.50    0.50    --  -90.00 -76.00   2.50   50
 96  ω   -157.00-101.00   0.50    0.50    --  -90.00 -76.00   2.50  112
 97  ω    -95.00 -69.00   0.50    0.50    --  -94.00 -76.00 170.22   52
 98  ω   -161.00 -71.00   0.50    0.50    --  -94.00 -69.00-108.01  180
 99  ω    -96.00 -71.00   0.50    0.50    --  -94.00 -71.00 -30.64   50
100  ω   -160.00-121.00   0.50    0.50    --  -94.00 -71.00 -30.64   78
101  ω   -138.00 -71.00   0.50    0.50    --  -95.95 -77.00-150.00  134
102  ω    -57.00 -32.00   0.50    0.50    --  -95.95  50.00 120.00   50
103  ω    -98.00 -73.00   0.50    0.50    --  -95.95 -77.00-120.00   50
104  ω   -128.00-102.00   0.50    0.50    --  -95.95 -77.00-120.00   52
105  ω   -137.00 -74.00   0.50    0.50    --  -95.95 -68.00 120.00  126
106  ω   -125.00 -90.00   0.50    0.50    --  -95.95 142.00-168.32   70
107  ω    -80.00 -29.00   0.50    0.50    --  -95.95  68.00 150.00  102
108  ω   -156.00 -75.00   0.50    0.50    --  -95.95 -68.00 150.00  162
109  ω   -163.00 -71.00   0.50    0.50    --  -95.95 -76.00-132.87  184
110  ω    -74.00 -37.00   0.50    0.50    --  -95.95 142.00-168.32   74
111  ω   -135.00 -80.00   0.50    0.50    --  -95.95 -59.00 -90.00  110
112  ω   -161.00 -74.00   0.50    0.50    --  -95.95 -68.00  60.00  174
113  ω    -57.00 -30.00   0.50    0.50    --  -95.95  50.00 150.00   54
114  ω   -101.00 -76.00   0.50    0.50    --  -95.95 -68.00 -90.00   50
115  ω   -123.00 -71.00   0.50    0.50    --  -95.95 -77.00  30.00  104
116  ω    -69.00 -27.00   0.50    0.50    --  -95.95  96.00 -90.00   84
117  ω   -112.00 -71.00   0.50    0.50    --  -95.95 -77.00-180.00   82
118  ω   -155.00-124.00   0.50    0.50    --  -95.95 -77.00-180.00   62
119  ω    -56.00 -30.00   0.50    0.50    --  -95.95  50.00 -90.00   52
120  ω   -162.00-103.00   0.50    0.50    --  -95.95 -59.00 -60.00  118
121  ω    -57.00 -31.00   0.50    0.50    --  -95.95  50.00 -60.00   52
122  ω   -153.00 -71.00   0.50    0.50    --  -95.95 -77.00  90.00  164
123  ω   -162.00-118.00   0.50    0.50    --  -95.95 -42.00 -30.00   88
124  ω    -83.00 -46.00   0.50    0.50    --  -95.95  68.00 -30.00   74
125  ω    125.00 150.00   0.50    0.50    --   97.51  77.00 -60.00   50
126  ω     50.00 104.00   0.50    0.50    --   97.51 -77.00  60.00  108
127  ω     73.00 118.00   0.50    0.50    --   97.51  77.00 -60.00   90
128  ω    128.00 164.00   0.50    0.50    --   97.51  77.00-150.00   72
129  ω     73.00  98.00   0.50    0.50    --   97.51  77.00-150.00   50
130  ω     32.00  69.00   0.50    0.50    --   97.51 -59.00-180.00   74
131  ω     49.00 107.00   0.50    0.50    --   97.51-117.00-150.00  116
132  ω     73.00 156.00   0.50    0.50    --   97.51  77.00 -30.00  166
133  ω     52.00  90.00   0.50    0.50    --   97.51 -96.00-150.00   76
134  ω     32.00 126.00   0.50    0.50    --   97.51-145.00  30.00  188
135  ω    122.00 151.00   0.50    0.50    --   97.51  77.00  60.00   58
136  ω     73.00  99.00   0.50    0.50    --   97.51  77.00  60.00   52
137  ω     36.00 107.00   0.50    0.50    --   97.51-117.00  90.00  142
138  ω    140.00 165.00   0.50    0.50    --   97.51  77.00   0.00   50
139  ω     73.00 131.00   0.50    0.50    --   97.51  77.00   0.00  116
140  ω     36.00  83.00   0.50    0.50    --   97.51 -68.00 -30.00   94
141  ω     32.00  68.00   0.50    0.50    --   97.51 -59.00   0.00   72
142  ω     56.00  83.00   0.50    0.50    --   97.51 -68.00-150.00   54
143  ω    137.00 162.00   0.50    0.50    --   97.51  68.00 120.00   50
144  ω     79.00 117.00   0.50    0.50    --   97.51  68.00 120.00   76
145  ω     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       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_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_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_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_coef       .
_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_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0242
_refine_ls_restrained_S_all      1.033
_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)+(0.0383P)²+0.3430P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0621
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Cl1A Cl 0.22062(5) 0.82226(4) 0.62451(4) 0.02598(12) Uani 1 1 d . . . . .
Cl1 Cl -0.16096(5) 0.96576(4) 0.10270(4) 0.02712(12) Uani 1 1 d . . . . .
N1A N 0.27844(16) 0.67350(12) 0.41148(15) 0.0166(3) Uani 1 1 d . . . . .
N2A N 0.13653(16) 0.61650(12) 0.24871(15) 0.0178(3) Uani 1 1 d . . . . .
N1 N 0.13363(16) 0.87353(12) 0.13687(14) 0.0167(3) Uani 1 1 d . . . . .
N2 N 0.30487(17) 0.90361(13) 0.28803(15) 0.0204(3) Uani 1 1 d . . . . .
N3 N 0.19971(19) 1.07492(14) -0.02131(17) 0.0273(4) Uani 1 1 d . . . . .
N3A N 0.28666(19) 0.44549(14) 0.55687(18) 0.0309(4) Uani 1 1 d . . . . .
C5A C 0.07288(19) 0.67730(14) 0.31399(17) 0.0166(4) Uani 1 1 d . . . . .
C15 C -0.0025(2) 0.76138(15) -0.00699(18) 0.0194(4) Uani 1 1 d . . . . .
H15 H -0.0086 0.7178 0.0568 0.023 Uiso 1 1 calc R U . . .
C7 C 0.26390(19) 0.85816(14) 0.18450(17) 0.0175(4) Uani 1 1 d . . . . .
C16 C -0.06118(19) 0.73788(15) -0.12503(19) 0.0208(4) Uani 1 1 d . . . . .
H16 H -0.1057 0.6772 -0.1421 0.025 Uiso 1 1 calc R U . . .
C7A C 0.25737(19) 0.61516(14) 0.30831(17) 0.0166(4) Uani 1 1 d . . . . .
C6A C 0.15961(18) 0.71385(14) 0.41599(17) 0.0164(4) Uani 1 1 d . . . . .
C1 C -0.02539(19) 0.98242(15) 0.21794(18) 0.0198(4) Uani 1 1 d . . . . .
C8 C 0.3515(2) 0.80221(14) 0.12593(18) 0.0190(4) Uani 1 1 d . . . . .
C6 C 0.0914(2) 0.93718(14) 0.21644(17) 0.0179(4) Uani 1 1 d . . . . .
C14A C 0.39289(19) 0.68115(15) 0.50469(17) 0.0177(4) Uani 1 1 d . . . . .
C8A C 0.3581(2) 0.55886(14) 0.26796(17) 0.0179(4) Uani 1 1 d . . . . .
C4A C -0.05690(19) 0.70478(14) 0.28876(17) 0.0187(4) Uani 1 1 d . . . . .
H4A H -0.1160 0.6791 0.2207 0.022 Uiso 1 1 calc R U . . .
C13 C 0.3133(2) 0.72610(15) 0.04296(19) 0.0216(4) Uani 1 1 d . . . . .
H13 H 0.2254 0.7074 0.0213 0.026 Uiso 1 1 calc R U . . .
C20 C 0.1419(2) 1.00373(15) -0.04780(18) 0.0198(4) Uani 1 1 d . . . . .
C9A C 0.4882(2) 0.58257(16) 0.29672(18) 0.0220(4) Uani 1 1 d . . . . .
H9A H 0.5175 0.6366 0.3484 0.026 Uiso 1 1 calc R U . . .
C1A C 0.1176(2) 0.77819(14) 0.49517(18) 0.0184(4) Uani 1 1 d . . . . .
C18A C 0.5306(2) 0.61322(16) 0.6841(2) 0.0239(4) Uani 1 1 d . . . . .
H18A H 0.5521 0.5616 0.7413 0.029 Uiso 1 1 calc R U . . .
C17 C -0.0554(2) 0.80223(15) -0.21848(18) 0.0223(4) Uani 1 1 d . . . . .
H17 H -0.0964 0.7854 -0.2988 0.027 Uiso 1 1 calc R U . . .
C19A C 0.42430(19) 0.60430(14) 0.58773(18) 0.0182(4) Uani 1 1 d . . . . .
C11 C 0.5316(2) 0.70267(16) 0.0244(2) 0.0253(5) Uani 1 1 d . . . . .
H11 H 0.5925 0.6694 -0.0107 0.030 Uiso 1 1 calc R U . . .
C9 C 0.48236(19) 0.82630(16) 0.15857(18) 0.0224(4) Uani 1 1 d . . . . .
H9 H 0.5105 0.8771 0.2156 0.027 Uiso 1 1 calc R U . . .
C5 C 0.19927(19) 0.95383(15) 0.31019(18) 0.0199(4) Uani 1 1 d . . . . .
C12A C 0.4042(2) 0.42449(16) 0.1445(2) 0.0255(5) Uani 1 1 d . . . . .
H12A H 0.3753 0.3704 0.0926 0.031 Uiso 1 1 calc R U . . .
C2A C -0.00978(19) 0.80726(14) 0.46804(17) 0.0191(4) Uani 1 1 d . . . . .
H2A H -0.0393 0.8528 0.5191 0.023 Uiso 1 1 calc R U . . .
C18 C 0.0096(2) 0.89067(15) -0.19507(18) 0.0216(4) Uani 1 1 d . . . . .
H18 H 0.0125 0.9351 -0.2588 0.026 Uiso 1 1 calc R U . . .
C13A C 0.3169(2) 0.47924(16) 0.19077(18) 0.0222(4) Uani 1 1 d . . . . .
H13A H 0.2282 0.4627 0.1700 0.027 Uiso 1 1 calc R U . . .
C19 C 0.07091(19) 0.91400(14) -0.07675(18) 0.0174(4) Uani 1 1 d . . . . .
C4 C 0.1921(2) 1.01480(16) 0.40739(19) 0.0250(4) Uani 1 1 d . . . . .
H4 H 0.2649 1.0255 0.4713 0.030 Uiso 1 1 calc R U . . .
C2 C -0.0324(2) 1.04335(15) 0.3136(2) 0.0242(4) Uani 1 1 d . . . . .
H2 H -0.1112 1.0750 0.3158 0.029 Uiso 1 1 calc R U . . .
C15A C 0.4686(2) 0.76491(15) 0.51493(19) 0.0213(4) Uani 1 1 d . . . . .
H15A H 0.4479 0.8165 0.4576 0.026 Uiso 1 1 calc R U . . .
C10A C 0.5757(2) 0.52705(17) 0.24974(19) 0.0263(5) Uani 1 1 d . . . . .
H10A H 0.6645 0.5433 0.2701 0.032 Uiso 1 1 calc R U . . .
C12 C 0.4022(2) 0.67777(17) -0.0078(2) 0.0253(4) Uani 1 1 d . . . . .
H12 H 0.3746 0.6271 -0.0653 0.030 Uiso 1 1 calc R U . . .
C11A C 0.5340(2) 0.44846(16) 0.17363(19) 0.0257(5) Uani 1 1 d . . . . .
H11A H 0.5938 0.4112 0.1415 0.031 Uiso 1 1 calc R U . . .
C20A C 0.3474(2) 0.51618(16) 0.57165(19) 0.0216(4) Uani 1 1 d . . . . .
C14 C 0.06494(18) 0.84876(14) 0.01700(17) 0.0164(4) Uani 1 1 d . . . . .
C3 C 0.0758(2) 1.05880(16) 0.4073(2) 0.0262(5) Uani 1 1 d . . . . .
H3 H 0.0687 1.1006 0.4723 0.031 Uiso 1 1 calc R U . . .
C17A C 0.6041(2) 0.69795(17) 0.6954(2) 0.0260(5) Uani 1 1 d . . . . .
H17A H 0.6752 0.7053 0.7619 0.031 Uiso 1 1 calc R U . . .
C10 C 0.5710(2) 0.77667(17) 0.1085(2) 0.0262(5) Uani 1 1 d . . . . .
H10 H 0.6595 0.7934 0.1318 0.031 Uiso 1 1 calc R U . . .
C16A C 0.5749(2) 0.77254(17) 0.6099(2) 0.0252(4) Uani 1 1 d . . . . .
H16A H 0.6282 0.8292 0.6167 0.030 Uiso 1 1 calc R U . . .
C3A C -0.0962(2) 0.77036(15) 0.36598(18) 0.0190(4) Uani 1 1 d . . . . .
H3A H -0.1835 0.7909 0.3498 0.023 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Cl1A C1A 1.736(2) . ?
Cl1 C1 1.738(2) . ?
N1A C7A 1.394(3) . ?
N1A C6A 1.393(3) . ?
N1A C14A 1.432(3) . ?
N2A C5A 1.386(2) . ?
N2A C7A 1.317(3) . ?
N1 C7 1.390(3) . ?
N1 C6 1.398(3) . ?
N1 C14 1.438(2) . ?
N2 C7 1.317(3) . ?
N2 C5 1.388(3) . ?
N3 C20 1.150(3) . ?
N3A C20A 1.149(3) . ?
C5A C6A 1.405(3) . ?
C5A C4A 1.401(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(3) . ?
C15 C14 1.383(3) . ?
C7 C8 1.475(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.389(3) . ?
C7A C8A 1.474(3) . ?
C6A C1A 1.400(3) . ?
C1 C6 1.393(3) . ?
C1 C2 1.384(3) . ?
C8 C13 1.399(3) . ?
C8 C9 1.401(3) . ?
C6 C5 1.403(3) . ?
C14A C19A 1.399(3) . ?
C14A C15A 1.385(3) . ?
C8A C9A 1.390(3) . ?
C8A C13A 1.402(3) . ?
C4A H4A 0.9500 . ?
C4A C3A 1.381(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.382(3) . ?
C20 C19 1.434(3) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.397(3) . ?
C1A C2A 1.383(3) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.396(3) . ?
C18A C17A 1.383(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(3) . ?
C19A C20A 1.440(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(3) . ?
C11 C10 1.387(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(3) . ?
C5 C4 1.399(3) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.386(3) . ?
C12A C11A 1.388(3) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.405(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.397(3) . ?
C13A H13A 0.9500 . ?
C19 C14 1.400(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.377(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.402(3) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.386(3) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.385(3) . ?
C12 H12 0.9500 . ?
C11A H11A 0.9500 . ?
C3 H3 0.9500 . ?
C17A H17A 0.9500 . ?
C17A C16A 1.392(3) . ?
C10 H10 0.9500 . ?
C16A H16A 0.9500 . ?
C3A H3A 0.9500 . ?

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
C7A N1A C14A 128.11(16) . . ?
C6A N1A C7A 106.14(16) . . ?
C6A N1A C14A 125.22(16) . . ?
C7A N2A C5A 105.79(16) . . ?
C7 N1 C6 106.17(16) . . ?
C7 N1 C14 126.07(16) . . ?
C6 N1 C14 126.20(16) . . ?
C7 N2 C5 105.83(17) . . ?
N2A C5A C6A 110.08(17) . . ?
N2A C5A C4A 128.96(18) . . ?
C4A C5A C6A 120.95(18) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.41(19) . . ?
N1 C7 C8 125.46(17) . . ?
N2 C7 N1 112.48(18) . . ?
N2 C7 C8 121.98(18) . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.67(19) . . ?
C17 C16 H16 119.7 . . ?
N1A C7A C8A 124.50(17) . . ?
N2A C7A N1A 112.48(17) . . ?
N2A C7A C8A 123.02(17) . . ?
N1A C6A C5A 105.51(17) . . ?
N1A C6A C1A 133.98(18) . . ?
C1A C6A C5A 120.50(18) . . ?
C6 C1 Cl1 121.97(16) . . ?
C2 C1 Cl1 119.41(16) . . ?
C2 C1 C6 118.62(19) . . ?
C13 C8 C7 124.61(18) . . ?
C13 C8 C9 118.36(19) . . ?
C9 C8 C7 117.01(18) . . ?
N1 C6 C5 105.37(17) . . ?
C1 C6 N1 134.39(19) . . ?
C1 C6 C5 120.25(18) . . ?
C19A C14A N1A 118.91(18) . . ?
C15A C14A N1A 120.45(18) . . ?
C15A C14A C19A 120.60(18) . . ?
C9A C8A C7A 124.41(18) . . ?
C9A C8A C13A 118.96(18) . . ?
C13A C8A C7A 116.56(18) . . ?
C5A C4A H4A 121.1 . . ?
C3A C4A C5A 117.89(19) . . ?
C3A C4A H4A 121.1 . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.7(2) . . ?
C12 C13 H13 119.7 . . ?
N3 C20 C19 178.1(2) . . ?
C8A C9A H9A 119.9 . . ?
C8A C9A C10A 120.1(2) . . ?
C10A C9A H9A 119.9 . . ?
C6A C1A Cl1A 121.97(16) . . ?
C2A C1A Cl1A 119.72(15) . . ?
C2A C1A C6A 118.31(18) . . ?
C19A C18A H18A 120.3 . . ?
C17A C18A H18A 120.3 . . ?
C17A C18A C19A 119.32(19) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.31(19) . . ?
C18 C17 H17 119.8 . . ?
C14A C19A C20A 119.39(18) . . ?
C18A C19A C14A 119.81(18) . . ?
C18A C19A C20A 120.80(18) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.3(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 H9 119.7 . . ?
N2 C5 C6 110.10(17) . . ?
N2 C5 C4 128.71(19) . . ?
C4 C5 C6 121.19(19) . . ?
C13A C12A H12A 119.9 . . ?
C13A C12A C11A 120.2(2) . . ?
C11A C12A H12A 119.9 . . ?
C1A C2A H2A 119.5 . . ?
C1A C2A C3A 120.92(18) . . ?
C3A C2A H2A 119.5 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.33(18) . . ?
C19 C18 H18 120.3 . . ?
C8A C13A H13A 119.7 . . ?
C12A C13A C8A 120.6(2) . . ?
C12A C13A H13A 119.7 . . ?
C18 C19 C20 121.62(18) . . ?
C18 C19 C14 120.08(19) . . ?
C14 C19 C20 118.30(18) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 C5 117.7(2) . . ?
C3 C4 H4 121.1 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C14A C15A H15A 120.4 . . ?
C14A C15A C16A 119.2(2) . . ?
C16A C15A H15A 120.4 . . ?
C9A C10A H10A 119.8 . . ?
C11A C10A C9A 120.5(2) . . ?
C11A C10A H10A 119.8 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12A C11A H11A 120.2 . . ?
C10A C11A C12A 119.66(19) . . ?
C10A C11A H11A 120.2 . . ?
N3A C20A C19A 178.7(2) . . ?
C15 C14 N1 121.38(17) . . ?
C15 C14 C19 120.17(18) . . ?
C19 C14 N1 118.42(17) . . ?
C4 C3 C2 121.6(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C18A C17A H17A 119.8 . . ?
C18A C17A C16A 120.5(2) . . ?
C16A C17A H17A 119.8 . . ?
C11 C10 H10 119.7 . . ?
C9 C10 C11 120.5(2) . . ?
C9 C10 H10 119.7 . . ?
C15A C16A C17A 120.6(2) . . ?
C15A C16A H16A 119.7 . . ?
C17A C16A H16A 119.7 . . ?
C4A C3A C2A 121.38(19) . . ?
C4A C3A H3A 119.3 . . ?
C2A C3A H3A 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1A C1A C2A C3A -177.99(15) . . . . ?
Cl1 C1 C6 N1 -0.3(3) . . . . ?
Cl1 C1 C6 C5 178.89(15) . . . . ?
Cl1 C1 C2 C3 -179.45(16) . . . . ?
N1A C7A C8A C9A -25.2(3) . . . . ?
N1A C7A C8A C13A 158.05(18) . . . . ?
N1A C6A C1A Cl1A -2.9(3) . . . . ?
N1A C6A C1A C2A 176.8(2) . . . . ?
N1A C14A C19A C18A -175.62(18) . . . . ?
N1A C14A C19A C20A 5.2(3) . . . . ?
N1A C14A C15A C16A 176.48(18) . . . . ?
N2A C5A C6A N1A -0.1(2) . . . . ?
N2A C5A C6A C1A 179.16(17) . . . . ?
N2A C5A C4A C3A -177.20(19) . . . . ?
N2A C7A C8A C9A 153.9(2) . . . . ?
N2A C7A C8A C13A -22.9(3) . . . . ?
N1 C7 C8 C13 -27.0(3) . . . . ?
N1 C7 C8 C9 154.53(19) . . . . ?
N1 C6 C5 N2 1.0(2) . . . . ?
N1 C6 C5 C4 -179.82(18) . . . . ?
N2 C7 C8 C13 156.4(2) . . . . ?
N2 C7 C8 C9 -22.1(3) . . . . ?
N2 C5 C4 C3 178.3(2) . . . . ?
C5A N2A C7A N1A -0.4(2) . . . . ?
C5A N2A C7A C8A -179.61(17) . . . . ?
C5A C6A C1A Cl1A 178.11(15) . . . . ?
C5A C6A C1A C2A -2.2(3) . . . . ?
C5A C4A C3A C2A -1.2(3) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C7 N1 C6 C1 177.4(2) . . . . ?
C7 N1 C6 C5 -1.9(2) . . . . ?
C7 N1 C14 C15 96.0(2) . . . . ?
C7 N1 C14 C19 -82.0(2) . . . . ?
C7 N2 C5 C6 0.3(2) . . . . ?
C7 N2 C5 C4 -178.8(2) . . . . ?
C7 C8 C13 C12 179.80(19) . . . . ?
C7 C8 C9 C10 179.46(18) . . . . ?
C16 C15 C14 N1 -176.28(18) . . . . ?
C16 C15 C14 C19 1.7(3) . . . . ?
C16 C17 C18 C19 0.9(3) . . . . ?
C7A N1A C6A C5A -0.1(2) . . . . ?
C7A N1A C6A C1A -179.3(2) . . . . ?
C7A N1A C14A C19A -74.6(3) . . . . ?
C7A N1A C14A C15A 107.7(2) . . . . ?
C7A N2A C5A C6A 0.3(2) . . . . ?
C7A N2A C5A C4A 178.9(2) . . . . ?
C7A C8A C9A C10A -177.20(19) . . . . ?
C7A C8A C13A C12A 177.45(18) . . . . ?
C6A N1A C7A N2A 0.4(2) . . . . ?
C6A N1A C7A C8A 179.53(17) . . . . ?
C6A N1A C14A C19A 95.9(2) . . . . ?
C6A N1A C14A C15A -81.8(2) . . . . ?
C6A C5A C4A C3A 1.3(3) . . . . ?
C6A C1A C2A C3A 2.3(3) . . . . ?
C1 C6 C5 N2 -178.38(18) . . . . ?
C1 C6 C5 C4 0.7(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C8 C13 C12 C11 1.3(3) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
C6 N1 C7 N2 2.2(2) . . . . ?
C6 N1 C7 C8 -174.73(18) . . . . ?
C6 N1 C14 C15 -100.3(2) . . . . ?
C6 N1 C14 C19 81.7(2) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C6 C5 C4 C3 -0.7(3) . . . . ?
C14A N1A C7A N2A 172.25(18) . . . . ?
C14A N1A C7A C8A -8.6(3) . . . . ?
C14A N1A C6A C5A -172.32(18) . . . . ?
C14A N1A C6A C1A 8.6(3) . . . . ?
C14A C15A C16A C17A -1.2(3) . . . . ?
C8A C9A C10A C11A 0.4(3) . . . . ?
C4A C5A C6A N1A -178.83(17) . . . . ?
C4A C5A C6A C1A 0.4(3) . . . . ?
C13 C8 C9 C10 0.8(3) . . . . ?
C20 C19 C14 N1 -2.0(3) . . . . ?
C20 C19 C14 C15 -179.97(18) . . . . ?
C9A C8A C13A C12A 0.5(3) . . . . ?
C9A C10A C11A C12A -0.4(3) . . . . ?
C1A C2A C3A C4A -0.7(3) . . . . ?
C18A C17A C16A C15A 2.6(3) . . . . ?
C17 C18 C19 C20 178.66(18) . . . . ?
C17 C18 C19 C14 -0.8(3) . . . . ?
C19A C14A C15A C16A -1.1(3) . . . . ?
C19A C18A C17A C16A -1.7(3) . . . . ?
C9 C8 C13 C12 -1.7(3) . . . . ?
C5 N2 C7 N1 -1.5(2) . . . . ?
C5 N2 C7 C8 175.53(17) . . . . ?
C5 C4 C3 C2 0.1(3) . . . . ?
C18 C19 C14 N1 177.52(17) . . . . ?
C18 C19 C14 C15 -0.5(3) . . . . ?
C13A C8A C9A C10A -0.5(3) . . . . ?
C13A C12A C11A C10A 0.3(3) . . . . ?
C2 C1 C6 N1 -179.5(2) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C15A C14A C19A C18A 2.0(3) . . . . ?
C15A C14A C19A C20A -177.11(18) . . . . ?
C12 C11 C10 C9 -0.9(3) . . . . ?
C11A C12A C13A C8A -0.4(3) . . . . ?
C14 N1 C7 N2 168.60(17) . . . . ?
C14 N1 C7 C8 -8.3(3) . . . . ?
C14 N1 C6 C1 11.1(3) . . . . ?
C14 N1 C6 C5 -168.25(17) . . . . ?
C14 C15 C16 C17 -1.6(3) . . . . ?
C17A C18A C19A C14A -0.6(3) . . . . ?
C17A C18A C19A C20A 178.54(19) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?

_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
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_in_2022_282
_database_code_depnum_ccdc_archive 'CCDC 2285267'
loop_
_audit_author_name
_audit_author_address
'Ivan Nemec'
;Faculty of Science, Palacky University in Olomouc
Czech Republic
;
_audit_update_record             
;
2023-07-28 deposited with the CCDC.	2024-07-04 downloaded from the CCDC.
;
_audit_creation_date             2023-03-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 Cl I N2'
_chemical_formula_sum            'C19 H12 Cl I N2'
_chemical_formula_weight         430.66
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
Cl Cl 0.3639 0.7018 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.66885(4)
_cell_length_b                   10.22838(6)
_cell_length_c                   18.76755(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1664.085(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    37492
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      69.6070
_cell_measurement_theta_min      4.2990
_shelx_estimated_absorpt_T_max   0.222
_shelx_estimated_absorpt_T_min   0.086
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 1 1 0.1506
2 -1 -1 0.1253
-1 1 0 0.1489
1 -1 0 0.1473
0 1 -1 0.1200
-1 -2 -2 0.0817
1 2 2 0.0679
-1 0 -2 0.0918
1 0 2 0.1088
2 2 1 0.0709
-2 -2 -1 0.0812
-1 -2 1 0.0810
1 2 1 0.0544
-1 -2 -1 0.0799
0 0 -1 0.0890
0 0 1 0.0822
0 -1 -1 0.0896
0 1 1 0.0879
0 -1 -2 0.0722
0 -1 2 0.1053
1 0 -2 0.1156
-1 -1 2 0.0983
-1 0 -1 0.1021
1 0 1 0.1021
2 1 1 0.0785

_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -64.00   0.50    0.20    --  -42.75 -66.00-108.00   76
  2  ω     74.00 108.00   0.50    0.20    --   44.32  66.00  26.00   68
  3  ω     22.00  48.00   0.50    0.20    --   44.32 -66.00-108.00   52
  4  ω   -103.00 -76.00   0.50    0.60    --  -95.95 -66.00-108.00   54
  5  ω    -78.00 -53.00   0.50    0.60    --  -95.95  66.00  26.00   50
  6  ω   -142.00-116.00   0.50    0.60    --  -95.95 -66.00-108.00   52
  7  ω     30.00  68.00   0.50    0.60    --   97.51 -66.00-108.00   76
  8  ω    121.00 147.00   0.50    0.60    --   97.51  66.00  26.00   52
  9  ω    -57.00 -32.00   0.50    0.20    --   14.00 162.00 -68.81   50
 10  ω    -59.00 -10.00   0.50    0.20    --  -14.00 120.00 171.53   98
 11  ω    -23.00   2.00   0.50    0.20    --   14.00 106.00 127.48   50
 12  ω    -69.00 -15.00   0.50    0.20    --  -18.00 130.00  38.29  108
 13  ω     -8.00  17.00   0.50    0.20    --   26.00 100.00 174.13   50
 14  ω     -3.00  22.00   0.50    0.20    --   30.00  98.00  15.36   50
 15  ω     -1.00  24.00   0.50    0.20    --   30.00  99.00  45.81   50
 16  ω      2.00  27.00   0.50    0.20    --   34.00  96.00 104.70   50
 17  ω      1.00  26.00   0.50    0.20    --   34.00  98.00-178.62   50
 18  ω      1.00  26.00   0.50    0.20    --   34.00  98.00  13.76   50
 19  ω      7.00  32.00   0.50    0.20    --   38.00  94.00 -99.64   50
 20  ω      9.00  34.00   0.50    0.20    --   38.00  89.00 -33.41   50
 21  ω      7.00  32.00   0.50    0.20    --   38.00  93.00 150.97   50
 22  ω    -32.00  -7.00   0.50    0.20    --  -38.00 -94.00 -27.11   50
 23  ω    -41.00 -12.00   0.50    0.20    --  -42.00 -91.00  49.02   58
 24  ω     13.00  38.00   0.50    0.20    --   42.00  89.00  12.44   50
 25  ω     13.00  38.00   0.50    0.20    --   42.00  87.00 -14.84   50
 26  ω    -67.00 -41.00   0.50    0.20    --  -42.75 138.00  90.00   52
 27  ω    -61.00  -9.00   0.50    0.20    --  -42.75  66.00  26.00  104
 28  ω     -1.00  25.00   0.50    0.20    --  -42.75  66.00  26.00   52
 29  ω    -76.00   4.00   0.50    0.20    --  -42.75 104.00 -30.00  160
 30  ω     16.00  41.00   0.50    0.20    --   46.00  90.00 178.67   50
 31  ω     16.00  41.00   0.50    0.20    --   46.00  91.00 152.99   50
 32  ω    -43.00 -18.00   0.50    0.20    --  -46.00 -90.00  54.55   50
 33  ω     16.00  41.00   0.50    0.20    --   46.00  90.00 129.26   50
 34  ω    -42.00 -16.00   0.50    0.20    --  -46.00 -91.00   8.39   52
 35  ω     16.00  41.00   0.50    0.20    --   46.00  92.00-141.66   50
 36  ω     16.00  41.00   0.50    0.20    --   46.00  92.00 -84.07   50
 37  ω    -52.00 -26.00   0.50    0.20    --  -50.00 -72.00 -69.24   52
 38  ω    -52.00 -27.00   0.50    0.20    --  -50.00 -71.00 148.45   50
 39  ω    -58.00 -32.00   0.50    0.20    --  -54.00 -74.00 -42.27   52
 40  ω    -61.00 -31.00   0.50    0.20    --  -54.00 -71.00-109.79   60
 41  ω    -56.00 -30.00   0.50    0.20    --  -54.00 -74.00 114.02   52
 42  ω    -67.00 -34.00   0.50    0.20    --  -58.00 -73.00-163.84   66
 43  ω    -60.00 -35.00   0.50    0.20    --  -58.00 -70.00 -31.48   50
 44  ω    -60.00 -35.00   0.50    0.20    --  -58.00 -69.00 -85.90   50
 45  ω    -61.00 -34.00   0.50    0.20    --  -58.00 -74.00  98.60   54
 46  ω     33.00  58.00   0.50    0.20    --   58.00  77.00 -67.93   50
 47  ω    -69.00 -34.00   0.50    0.20    --  -58.00 -75.00 149.97   70
 48  ω    -60.00 -35.00   0.50    0.20    --  -58.00 -72.00-146.32   50
 49  ω    -90.00 -36.00   0.50    0.20    --  -58.00 -71.00 177.54  108
 50  ω    -65.00 -39.00   0.50    0.20    --  -62.00 -71.00  29.12   52
 51  ω   -108.00 -83.00   0.50    0.20    --  -62.00 -70.00 -63.21   50
 52  ω    -79.00 -37.00   0.50    0.20    --  -62.00 -77.00  93.49   84
 53  ω   -126.00 -86.00   0.50    0.20    --  -62.00 -77.00  93.49   80
 54  ω    -65.00 -39.00   0.50    0.20    --  -62.00 -70.00 -63.21   52
 55  ω    -98.00 -43.00   0.50    0.20    --  -66.00 -77.00  31.35  110
 56  ω    -68.00 -42.00   0.50    0.20    --  -66.00 -76.00 168.75   52
 57  ω    -99.00 -47.00   0.50    0.60    --  -70.00 -71.00-108.83  104
 58  ω    -77.00 -45.00   0.50    0.60    --  -70.00 -76.00 137.37   64
 59  ω    -80.00 -45.00   0.50    0.60    --  -70.00 -76.00  68.34   70
 60  ω    -76.00 -48.00   0.50    0.60    --  -70.00 -77.00 -20.71   56
 61  ω    -74.00 -47.00   0.50    0.60    --  -70.00 -77.00  19.76   54
 62  ω   -137.00-111.00   0.50    0.60    --  -70.00 -77.00 -20.71   52
 63  ω   -138.00 -80.00   0.50    0.60    --  -70.00 -77.00  19.76  116
 64  ω    -83.00 -49.00   0.50    0.60    --  -74.00 -75.00  87.97   68
 65  ω    -75.00 -50.00   0.50    0.60    --  -74.00 -75.00-108.93   50
 66  ω    -98.00 -52.00   0.50    0.60    --  -74.00 -76.00 117.32   92
 67  ω    -91.00 -50.00   0.50    0.60    --  -74.00 -73.00-177.90   82
 68  ω    -92.00 -50.00   0.50    0.60    --  -74.00 -72.00 -58.08   84
 69  ω    -89.00 -50.00   0.50    0.60    --  -74.00 -76.00 -70.94   78
 70  ω    -97.00 -49.00   0.50    0.60    --  -74.00 -77.00-148.47   96
 71  ω   -139.00-113.00   0.50    0.60    --  -74.00 -77.00-148.47   52
 72  ω    -78.00 -50.00   0.50    0.60    --  -74.00 -72.00-140.59   56
 73  ω    -86.00 -53.00   0.50    0.60    --  -78.00 -75.00  52.39   66
 74  ω    -88.00 -55.00   0.50    0.60    --  -78.00 -73.00   5.07   66
 75  ω    -86.00 -55.00   0.50    0.60    --  -78.00 -73.00  34.71   62
 76  ω    -99.00 -53.00   0.50    0.60    --  -78.00 -76.00 -79.80   92
 77  ω    -93.00 -59.00   0.50    0.60    --  -82.00 -75.00  -3.29   68
 78  ω   -117.00 -58.00   0.50    0.60    --  -82.00 -74.00 -99.57  118
 79  ω    -95.00 -59.00   0.50    0.60    --  -82.00 -74.00 175.37   72
 80  ω   -147.00-121.00   0.50    0.60    --  -82.00 -75.00-153.27   52
 81  ω    -89.00 -57.00   0.50    0.60    --  -82.00 -77.00 114.51   64
 82  ω   -132.00 -59.00   0.50    0.60    --  -82.00 -76.00 -25.33  146
 83  ω    -96.00 -57.00   0.50    0.60    --  -82.00 -75.00  77.64   78
 84  ω   -141.00 -57.00   0.50    0.60    --  -82.00 -75.00 132.29  168
 85  ω    -82.00 -57.00   0.50    0.60    --  -82.00 -75.00-153.27   50
 86  ω   -108.00 -58.00   0.50    0.60    --  -82.00 -73.00 152.13  100
 87  ω   -132.00 -65.00   0.50    0.60    --  -86.00 -65.00-128.56  134
 88  ω    108.00 134.00   0.50    0.60    --   86.00  72.00  51.73   52
 89  ω     63.00  89.00   0.50    0.60    --   86.00  72.00  51.73   52
 90  ω   -109.00 -67.00   0.50    0.60    --  -90.00 -69.00  -5.50   84
 91  ω   -105.00 -67.00   0.50    0.60    --  -90.00 -69.00-154.28   76
 92  ω    -98.00 -65.00   0.50    0.60    --  -90.00 -77.00  71.84   66
 93  ω   -155.00-111.00   0.50    0.60    --  -90.00 -77.00  71.84   88
 94  ω    -99.00 -66.00   0.50    0.60    --  -90.00 -74.00 106.12   66
 95  ω    -93.00 -67.00   0.50    0.60    --  -90.00 -74.00  84.95   52
 96  ω   -119.00 -72.00   0.50    0.60    --  -94.00 -66.00 -65.10   94
 97  ω    -94.00 -69.00   0.50    0.60    --  -94.00 -75.00-122.28   50
 98  ω   -154.00 -77.00   0.50    0.60    --  -95.95 -68.00 120.00  154
 99  ω   -134.00 -74.00   0.50    0.60    --  -95.95 -68.00  30.00  120
100  ω   -110.00 -31.00   0.50    0.60    --  -95.95 117.00 -60.00  158
101  ω   -112.00 -74.00   0.50    0.60    --  -95.95 -67.00 112.42   76
102  ω   -160.00 -74.00   0.50    0.60    --  -95.95 -77.00-180.00  172
103  ω   -125.00 -74.00   0.50    0.60    --  -95.95 -73.00  82.75  102
104  ω    -56.00 -29.00   0.50    0.60    --  -95.95  50.00-150.00   54
105  ω   -110.00 -72.00   0.50    0.60    --  -95.95 117.00-180.00   76
106  ω   -110.00 -38.00   0.50    0.60    --  -95.95 117.00 -90.00  144
107  ω   -124.00 -73.00   0.50    0.60    --  -95.95 -77.00 -60.00  102
108  ω   -164.00-130.00   0.50    0.60    --  -95.95 -77.00 -60.00   68
109  ω    -57.00 -29.00   0.50    0.60    --  -95.95  50.00-180.00   56
110  ω    -66.00 -37.00   0.50    0.60    --  -95.95 117.00 120.00   58
111  ω    -56.00 -31.00   0.50    0.60    --  -95.95 117.00  90.00   50
112  ω   -127.00-102.00   0.50    0.60    --  -95.95 -17.00 150.00   50
113  ω    -93.00 -67.00   0.50    0.60    --  -95.95 117.00 120.00   52
114  ω   -107.00 -71.00   0.50    0.60    --  -95.95 117.00  90.00   72
115  ω   -157.00 -74.00   0.50    0.60    --  -95.95 -68.00 150.00  166
116  ω   -104.00 -72.00   0.50    0.60    --  -95.95 -77.00 -30.00   64
117  ω   -133.00-107.00   0.50    0.60    --  -95.95 -77.00 -30.00   52
118  ω   -164.00-138.00   0.50    0.60    --  -95.95 -17.00 150.00   52
119  ω     73.00 147.00   0.50    0.60    --   97.51  77.00-150.00  148
120  ω     31.00  56.00   0.50    0.60    --   97.51 -50.00-150.00   50
121  ω     81.00 141.00   0.50    0.60    --   97.51  59.00  90.00  120
122  ω     75.00 123.00   0.50    0.60    --   97.51  68.00-150.00   96
123  ω     75.00 109.00   0.50    0.60    --   97.51-117.00  90.00   68
124  ω     32.00  57.00   0.50    0.60    --   97.51 -50.00 -90.00   50
125  ω     33.00  59.00   0.50    0.60    --   97.51-117.00  90.00   52
126  ω     66.00 109.00   0.50    0.60    --   97.51-117.00  30.00   86
127  ω     96.00 131.00   0.50    0.60    --   97.51  68.00   0.00   70
128  ω     28.00  85.00   0.50    0.60    --   97.51 -96.00  30.00  114
129  ω     79.00 163.00   0.50    0.60    --   97.51  68.00 -30.00  168
130  ω     74.00 160.00   0.50    0.60    --   97.51  77.00 150.00  172
131  ω     29.00  74.00   0.50    0.60    --   97.51 -77.00  30.00   90
132  ω     33.00  77.00   0.50    0.60    --   97.51 -68.00  60.00   88
133  ω     74.00 159.00   0.50    0.60    --   97.51  77.00   0.00  170
134  ω    104.00 164.00   0.50    0.60    --   97.51  59.00 -90.00  120
135  ω     40.00  69.00   0.50    0.60    --   97.51 -59.00 150.00   58
136  ω     29.00 101.00   0.50    0.60    --   97.51 -77.00-150.00  144
137  ω     73.00 161.00   0.50    0.60    --   97.51  77.00-180.00  176
138  ω     73.00 151.00   0.50    0.60    --   97.51  77.00  30.00  156
139  ω     31.00 105.00   0.50    0.60    --   97.51 -77.00 120.00  148
140  ω     73.00 164.00   0.50    0.60    --   97.51  77.00-120.00  182
141  ω     73.00 158.00   0.50    0.60    --   97.51  77.00  60.00  170
142  ω     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       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_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_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_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_coef       .
_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_R_factor_all          0.0174
_refine_ls_R_factor_gt           0.0174
_refine_ls_restrained_S_all      1.116
_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/[σ²(Fo²)+(0.0270P)²+0.8347P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0460
_refine_ls_wR_factor_ref         0.0460
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
I1 I 0.75789(2) 0.11920(2) 0.70913(2) 0.02038(8) Uani 1 1 d . . . . .
Cl1 Cl 0.89641(10) 0.44298(9) 0.86891(5) 0.02807(19) Uani 1 1 d . . . . .
N3 N 0.3693(3) 0.3310(3) 0.77635(14) 0.0202(6) Uani 1 1 d . . . . .
N1 N 0.6129(3) 0.3980(3) 0.75408(14) 0.0185(6) Uani 1 1 d . . . . .
C12 C 1.0124(4) 0.4553(4) 0.63078(19) 0.0255(7) Uani 1 1 d . . . . .
H12 H 1.1016 0.4686 0.6023 0.031 Uiso 1 1 calc R U . . .
C9 C 0.7500(4) 0.4175(3) 0.71231(15) 0.0196(6) Uani 1 1 d . . . . .
C7 C 0.7059(4) 0.3979(3) 0.88373(17) 0.0221(7) Uani 1 1 d . . . . .
C2 C 0.4696(4) 0.3640(3) 0.72697(16) 0.0188(6) Uani 1 1 d . . . . .
C11 C 0.9634(4) 0.3298(4) 0.64568(18) 0.0230(7) Uani 1 1 d . . . . .
H11 H 1.0196 0.2570 0.6280 0.028 Uiso 1 1 calc R U . . .
C13 C 0.9319(4) 0.5622(3) 0.65730(18) 0.0238(7) Uani 1 1 d . . . . .
H13 H 0.9673 0.6483 0.6476 0.029 Uiso 1 1 calc R U . . .
C8 C 0.6020(4) 0.3814(3) 0.82738(16) 0.0203(6) Uani 1 1 d . . . . .
C5 C 0.4987(5) 0.3405(4) 0.96506(18) 0.0284(8) Uani 1 1 d . . . . .
H5 H 0.4648 0.3276 1.0127 0.034 Uiso 1 1 calc R U . . .
C3 C 0.4499(4) 0.3419(3) 0.84050(17) 0.0209(7) Uani 1 1 d . . . . .
C6 C 0.6523(4) 0.3778(4) 0.95259(18) 0.0269(7) Uani 1 1 d . . . . .
H6 H 0.7204 0.3895 0.9918 0.032 Uiso 1 1 calc R U . . .
C18 C 0.3475(4) 0.3718(4) 0.50739(18) 0.0292(8) Uani 1 1 d . . . . .
H18 H 0.3177 0.3736 0.4587 0.035 Uiso 1 1 calc R U . . .
C10 C 0.8315(4) 0.3098(3) 0.68666(17) 0.0194(6) Uani 1 1 d . . . . .
C4 C 0.3959(4) 0.3220(3) 0.90998(18) 0.0250(7) Uani 1 1 d . . . . .
H4 H 0.2922 0.2966 0.9188 0.030 Uiso 1 1 calc R U . . .
C14 C 0.8000(4) 0.5434(3) 0.69789(17) 0.0217(7) Uani 1 1 d . . . . .
H14 H 0.7443 0.6164 0.7157 0.026 Uiso 1 1 calc R U . . .
C20 C 0.3672(4) 0.2569(3) 0.61877(19) 0.0241(7) Uani 1 1 d . . . . .
H20 H 0.3506 0.1802 0.6463 0.029 Uiso 1 1 calc R U . . .
C15 C 0.4339(4) 0.3667(4) 0.65028(17) 0.0205(7) Uani 1 1 d . . . . .
C17 C 0.4131(4) 0.4814(4) 0.53820(18) 0.0269(8) Uani 1 1 d . . . . .
H17 H 0.4284 0.5581 0.5106 0.032 Uiso 1 1 calc R U . . .
C19 C 0.3250(4) 0.2589(4) 0.5475(2) 0.0289(8) Uani 1 1 d . . . . .
H19 H 0.2810 0.1834 0.5261 0.035 Uiso 1 1 calc R U . . .
C16 C 0.4570(4) 0.4794(4) 0.61004(18) 0.0229(7) Uani 1 1 d . . . . .
H16 H 0.5023 0.5546 0.6312 0.027 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
I1 C10 2.094(3) . ?
Cl1 C7 1.737(3) . ?
N3 C2 1.315(4) . ?
N3 C3 1.396(4) . ?
N1 C9 1.438(4) . ?
N1 C2 1.386(4) . ?
N1 C8 1.389(4) . ?
C12 H12 0.9500 . ?
C12 C11 1.381(5) . ?
C12 C13 1.389(5) . ?
C9 C10 1.395(4) . ?
C9 C14 1.385(5) . ?
C7 C8 1.399(4) . ?
C7 C6 1.389(5) . ?
C2 C15 1.473(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.393(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(5) . ?
C8 C3 1.401(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.405(5) . ?
C5 C4 1.378(5) . ?
C3 C4 1.400(5) . ?
C6 H6 0.9500 . ?
C18 H18 0.9500 . ?
C18 C17 1.384(6) . ?
C18 C19 1.392(6) . ?
C4 H4 0.9500 . ?
C14 H14 0.9500 . ?
C20 H20 0.9500 . ?
C20 C15 1.395(5) . ?
C20 C19 1.388(5) . ?
C15 C16 1.393(5) . ?
C17 H17 0.9500 . ?
C17 C16 1.401(5) . ?
C19 H19 0.9500 . ?
C16 H16 0.9500 . ?

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
C2 N3 C3 104.8(3) . . ?
C2 N1 C9 125.1(3) . . ?
C2 N1 C8 105.8(3) . . ?
C8 N1 C9 127.8(3) . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C10 C9 N1 119.8(3) . . ?
C14 C9 N1 119.6(3) . . ?
C14 C9 C10 120.6(3) . . ?
C8 C7 Cl1 121.5(3) . . ?
C6 C7 Cl1 120.4(3) . . ?
C6 C7 C8 118.1(3) . . ?
N3 C2 N1 113.5(3) . . ?
N3 C2 C15 123.7(3) . . ?
N1 C2 C15 122.8(3) . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 120.0(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 119.9 . . ?
N1 C8 C7 133.6(3) . . ?
N1 C8 C3 105.9(3) . . ?
C7 C8 C3 120.5(3) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.7(3) . . ?
N3 C3 C8 110.0(3) . . ?
N3 C3 C4 128.6(3) . . ?
C4 C3 C8 121.4(3) . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.3(3) . . ?
C19 C18 H18 119.9 . . ?
C9 C10 I1 120.8(2) . . ?
C11 C10 I1 119.8(3) . . ?
C11 C10 C9 119.4(3) . . ?
C5 C4 C3 117.5(3) . . ?
C5 C4 H4 121.2 . . ?
C3 C4 H4 121.2 . . ?
C9 C14 C13 119.6(3) . . ?
C9 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C15 120.4(3) . . ?
C20 C15 C2 119.1(3) . . ?
C16 C15 C2 121.0(3) . . ?
C16 C15 C20 119.8(3) . . ?
C18 C17 H17 119.9 . . ?
C18 C17 C16 120.1(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.8(3) . . ?
C20 C19 H19 120.1 . . ?
C15 C16 C17 119.6(3) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C7 C8 N1 -2.7(6) . . . . ?
Cl1 C7 C8 C3 178.4(3) . . . . ?
Cl1 C7 C6 C5 -179.6(3) . . . . ?
N3 C2 C15 C20 -51.6(5) . . . . ?
N3 C2 C15 C16 124.5(4) . . . . ?
N3 C3 C4 C5 -179.3(3) . . . . ?
N1 C9 C10 I1 -0.6(4) . . . . ?
N1 C9 C10 C11 179.4(3) . . . . ?
N1 C9 C14 C13 -179.7(3) . . . . ?
N1 C2 C15 C20 129.3(3) . . . . ?
N1 C2 C15 C16 -54.6(5) . . . . ?
N1 C8 C3 N3 1.5(4) . . . . ?
N1 C8 C3 C4 -177.0(3) . . . . ?
C12 C11 C10 I1 -179.9(3) . . . . ?
C12 C11 C10 C9 0.0(5) . . . . ?
C12 C13 C14 C9 0.6(5) . . . . ?
C9 N1 C2 N3 169.4(3) . . . . ?
C9 N1 C2 C15 -11.4(5) . . . . ?
C9 N1 C8 C7 11.9(6) . . . . ?
C9 N1 C8 C3 -169.2(3) . . . . ?
C7 C8 C3 N3 -179.4(3) . . . . ?
C7 C8 C3 C4 2.1(5) . . . . ?
C2 N3 C3 C8 -0.5(4) . . . . ?
C2 N3 C3 C4 177.8(3) . . . . ?
C2 N1 C9 C10 -77.2(4) . . . . ?
C2 N1 C9 C14 102.8(4) . . . . ?
C2 N1 C8 C7 179.3(4) . . . . ?
C2 N1 C8 C3 -1.8(4) . . . . ?
C2 C15 C16 C17 -176.1(3) . . . . ?
C11 C12 C13 C14 -1.2(5) . . . . ?
C13 C12 C11 C10 0.9(5) . . . . ?
C8 N1 C9 C10 87.9(4) . . . . ?
C8 N1 C9 C14 -92.1(4) . . . . ?
C8 N1 C2 N3 1.6(4) . . . . ?
C8 N1 C2 C15 -179.2(3) . . . . ?
C8 C7 C6 C5 0.8(5) . . . . ?
C8 C3 C4 C5 -1.1(5) . . . . ?
C3 N3 C2 N1 -0.7(4) . . . . ?
C3 N3 C2 C15 -179.8(3) . . . . ?
C6 C7 C8 N1 176.9(4) . . . . ?
C6 C7 C8 C3 -1.9(5) . . . . ?
C6 C5 C4 C3 -0.1(5) . . . . ?
C18 C17 C16 C15 -0.2(6) . . . . ?
C10 C9 C14 C13 0.3(5) . . . . ?
C4 C5 C6 C7 0.2(6) . . . . ?
C14 C9 C10 I1 179.4(2) . . . . ?
C14 C9 C10 C11 -0.6(5) . . . . ?
C20 C15 C16 C17 -0.1(5) . . . . ?
C15 C20 C19 C18 -0.9(5) . . . . ?
C17 C18 C19 C20 0.7(6) . . . . ?
C19 C18 C17 C16 -0.1(6) . . . . ?
C19 C20 C15 C2 176.7(3) . . . . ?
C19 C20 C15 C16 0.6(5) . . . . ?

_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
;
