#------------------------------------------------------------------------------
#$Date: 2023-09-05 23:07:50 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286161 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/26/7062619.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_7062619
loop_
_publ_author_name
'Rahman, Noimur'
'Kushwah, Nisha'
'Priyadarsini, K. Indira'
_publ_section_title
;
 A redox active organodiselenide as an efficacious catalyst for the
 synthesis of oxygen-containing heterocyclic compounds
;
_journal_issue                   33
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15686
_journal_page_last               15693
_journal_paper_doi               10.1039/D3NJ01423A
_journal_volume                  47
_journal_year                    2023
_chemical_formula_sum            'C18 H17 Cl N2 O2'
_chemical_formula_weight         328.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2023-03-17 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.1240(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.41130(10)
_cell_length_b                   16.82570(10)
_cell_length_c                   10.91390(10)
_cell_measurement_reflns_used    42907
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      77.1160
_cell_measurement_theta_min      2.6200
_cell_volume                     1600.99(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Ortep 3 for windows'
_computing_publication_material  'WinGX 2021.3'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     31.00  56.50   0.50    0.20    --   54.00  79.00 -56.08   51
  2  ω     36.00  71.50   0.50    0.20    --   48.29  37.00-120.00   71
  3  ω     76.00 110.00   0.50    0.20    --   48.29  37.00-120.00   68
  4  ω     94.00 119.50   0.50    0.20    --   54.00  79.00 -56.08   51
  5  ω    100.80 126.30   0.50    0.20    --   54.00  80.00 -27.29   51
  6  ω     85.00 111.00   0.50    0.20    --   54.00  78.00   7.50   52
  7  ω    116.00 142.00   0.50    0.80    --  107.75 133.00  63.00   52
  8  ω    124.00 150.00   0.50    0.80    --  107.75  77.00  90.00   52
  9  ω    143.00 171.00   0.50    0.80    --  107.75  77.00 120.00   56
 10  ω    126.00 168.00   0.50    0.80    --  107.75  77.00 150.00   84
 11  ω     85.00 137.00   0.50    0.80    --  107.75  77.00  30.00  104
 12  ω    144.00 175.50   0.50    0.80    --  107.75  77.00   0.00   63
 13  ω    132.00 174.00   0.50    0.80    --  107.75  77.00 -60.00   84
 14  ω    142.00 176.00   0.50    0.80    --  107.75  77.00-120.00   68
 15  ω    132.00 170.00   0.50    0.80    --  107.75  45.00-150.00   76
 16  ω    120.00 146.00   0.50    0.80    --  107.75  77.00-180.00   52
 17  ω    119.00 176.50   0.50    0.80    --  107.75  77.00-150.00  115
 18  ω    149.00 175.00   0.50    0.80    --  107.75 125.00-150.00   52
 19  ω    129.00 175.00   0.50    0.80    --  107.75 125.00 -90.00   92
 20  ω    129.00 177.00   0.50    0.80    --  107.75  77.00 -30.00   96
 21  ω    125.00 172.50   0.50    0.80    --  107.75  45.00   0.00   95
 22  ω    109.00 134.50   0.50    0.80    --  107.75 136.00-119.00   51
 23  ω    105.00 131.00   0.50    0.80    --  107.75 125.00-150.00   52
 24  ω     94.00 176.00   0.50    0.80    --  107.75  77.00 -90.00  164
 25  ω     93.00 149.00   0.50    0.80    --  107.75  61.00 -30.00  112
 26  ω     92.00 145.50   0.50    0.80    --  107.75  61.00 -90.00  107
 27  ω     91.00 165.00   0.50    0.80    --  107.75  61.00-180.00  148
 28  ω     86.00 125.50   0.50    0.80    --  107.75  77.00 -60.00   79
 29  ω     85.00 124.50   0.50    0.80    --  107.75  77.00 -30.00   79
 30  ω     94.00 163.50   0.50    0.80    --  107.75  61.00  30.00  139
 31  ω     93.00 118.50   0.50    0.80    --  107.75  77.00  90.00   51
 32  ω     93.00 173.00   0.50    0.80    --  107.75  61.00 150.00  160
 33  ω     93.00 167.00   0.50    0.80    --  107.75  61.00 120.00  148
 34  ω     85.00 136.50   0.50    0.80    --  107.75  77.00 120.00  103
 35  ω     96.00 172.00   0.50    0.80    --  107.75  61.00  90.00  152
 36  ω     91.00 155.00   0.50    0.80    --  107.75  61.00 -60.00  128
 37  ω     86.00 116.00   0.50    0.80    --  107.75  77.00-180.00   60
 38  ω     86.00 114.00   0.50    0.80    --  107.75  77.00-150.00   56
 39  ω     85.00 127.00   0.50    0.80    --  107.75  77.00-120.00   84
 40  ω     93.00 133.00   0.50    0.80    --  107.75  61.00-150.00   80
 41  ω     79.00 155.00   0.50    0.80    --  102.00  79.00-138.57  152
 42  ω     91.00 126.50   0.50    0.80    --  107.75  61.00   0.00   71
 43  ω     91.00 175.00   0.50    0.80    --  107.75  61.00  60.00  168
 44  ω     86.00 115.50   0.50    0.80    --  107.75  77.00 150.00   59
 45  ω     72.00 129.50   0.50    0.20    --   58.00  80.00 135.85  115
 46  ω     85.00 143.00   0.50    0.80    --  107.75  77.00  60.00  116
 47  ω     85.00 132.50   0.50    0.80    --  107.75  77.00   0.00   95
 48  ω     64.00  90.00   0.50    0.20    --   54.00  80.00-121.53   52
 49  ω     37.00  72.50   0.50    0.20    --   58.00  74.00 -77.91   71
 50  ω     41.00  68.50   0.50    0.20    --   62.00  72.00-105.59   55
 51  ω     30.00  55.50   0.50    0.20    --   54.00  80.00-121.53   51
 52  ω     39.00  64.50   0.50    0.20    --   62.00  79.00-174.36   51
 53  ω     41.00  66.50   0.50    0.20    --   62.00  74.00-177.90   51
 54  ω     10.00  35.50   0.50    0.20    --   38.00  88.00 -91.78   51
 55  ω     30.00  55.50   0.50    0.20    --   54.00  80.00 -27.29   51
 56  ω     39.00  69.00   0.50    0.20    --   58.00  72.00 -13.71   60
 57  ω     41.00  67.00   0.50    0.20    --   62.00  73.00   9.53   52
 58  ω     30.00  68.00   0.50    0.20    --   54.00  80.00  30.00   76
 59  ω     42.00  67.50   0.50    0.20    --   62.00  72.00  90.89   51
 60  ω     39.00  64.50   0.50    0.20    --   62.00  78.00 106.72   51
 61  ω     34.00  59.50   0.50    0.20    --   58.00  80.00 135.85   51
 62  ω     39.00 122.50   0.50    0.20    --   48.29  19.00 120.00  167
 63  ω     40.00  66.00   0.50    0.80    --  107.75 -94.00   0.00   52
 64  ω     75.00 101.00   0.50    0.80    --  107.75 -94.00   0.00   52
 65  ω     80.00 117.50   0.50    0.80    --  107.75-133.00  -5.00   75
 66  ω     79.00 108.50   0.50    0.80    --  107.75-125.00 -60.00   59
 67  ω     82.00 111.50   0.50    0.80    --  107.75-125.00 -30.00   59
 68  ω     70.00 111.50   0.50    0.80    --  107.75-125.00 -90.00   83
 69  ω     48.00 109.50   0.50    0.80    --  107.75-125.00  30.00  123
 70  ω     84.00 110.00   0.50    0.80    --  107.75-125.00  90.00   52
 71  ω     71.00 119.00   0.50    0.80    --  107.75-136.00 176.00   96
 72  ω     59.00  99.00   0.50    0.80    --  107.75 -94.00 150.00   80
 73  ω     54.00 111.50   0.50    0.80    --  107.75-125.00 150.00  115
 74  ω     41.00  98.50   0.50    0.20    --   48.29-136.00 176.00  115
 75  ω     35.00  96.50   0.50    0.80    --  107.75 -94.00  90.00  123
 76  ω     42.00 107.50   0.50    0.80    --  107.75-125.00   0.00  131
 77  ω     40.00  99.50   0.50    0.20    --   48.29-133.00  -5.00  119
 78  ω     39.00  69.00   0.50    0.80    --  107.75 -77.00 -90.00   60
 79  ω     42.00  67.50   0.50    0.80    --  107.75 -61.00-150.00   51
 80  ω     37.00  91.00   0.50    0.80    --  107.75 -77.00-150.00  108
 81  ω     35.00  60.50   0.50    0.80    --  107.75 -61.00-120.00   51
 82  ω     39.00  83.00   0.50    0.80    --  107.75 -77.00-180.00   88
 83  ω     35.00  60.50   0.50    0.80    --  107.75-125.00 -90.00   51
 84  ω     38.00  63.50   0.50    0.80    --  107.75-125.00 -60.00   51
 85  ω     35.00  88.50   0.50    0.80    --  107.75 -77.00  30.00  107
 86  ω     38.00  64.00   0.50    0.80    --  107.75 -61.00  30.00   52
 87  ω     37.00 105.00   0.50    0.80    --  107.75 -94.00  30.00  136
 88  ω     35.00  68.50   0.50    0.80    --  107.75 -61.00 -90.00   67
 89  ω     45.00  70.50   0.50    0.80    --  107.75 -61.00 -30.00   51
 90  ω     43.00 103.00   0.50    0.80    --  107.75 -94.00-180.00  120
 91  ω     12.00  38.00   0.50    0.20    --   38.00  91.00  35.42   52
 92  ω     32.00  57.50   0.50    0.20    --   54.00  78.00   7.50   51
 93  ω      7.00  32.50   0.50    0.20    --   38.00  94.00   6.10   51
 94  ω    -11.00  23.00   0.50    0.20    --   18.00  95.00  -6.41   68
 95  ω     12.00  37.50   0.50    0.20    --   38.00  84.00 148.18   51
 96  ω    -15.00  17.00   0.50    0.20    --   18.00  98.00 166.02   64
 97  ω    -62.00 -37.50   0.50    0.20    --  -48.29 133.00  63.00   49
 98  ω    -78.00 -53.50   0.50    0.80    --  -86.25 133.00  63.00   49
 99  ω    -80.00 -55.50   0.50    0.20    --  -48.29 136.00-119.00   49
100  ω    -73.00 -47.50   0.50    0.20    --  -66.00 -67.00-126.04   51
101  ω    -58.00 -32.00   0.50    0.20    --  -54.00 -76.00-141.60   52
102  ω    -70.00 -44.00   0.50    0.20    --  -66.00 -79.00-172.51   52
103  ω    -78.00 -52.50   0.50    0.80    --  -70.00 -64.00 -95.39   51
104  ω    -76.00 -50.50   0.50    0.80    --  -74.00 -79.00-136.70   51
105  ω    -85.00 -59.50   0.50    0.80    --  -82.00 -77.00-102.75   51
106  ω    -86.00 -60.00   0.50    0.80    --  -82.00 -78.00 -67.35   52
107  ω    -81.00 -55.50   0.50    0.80    --  -78.00 -76.00 -36.64   51
108  ω    -63.00 -37.50   0.50    0.20    --  -58.00 -73.00   9.68   51
109  ω    -71.00 -27.00   0.50    0.20    --  -48.29 -77.00  60.00   88
110  ω    -78.00 -52.50   0.50    0.80    --  -70.00 -68.00  67.07   51
111  ω    -76.20 -50.70   0.50    0.80    --  -70.00 -68.00 114.58   51
112  ω    -77.00 -51.50   0.50    0.80    --  -70.00 -67.00  44.50   51
113  ω    -81.00 -55.50   0.50    0.80    --  -74.00 -65.00  -2.13   51
114  ω    -85.00 -59.50   0.50    0.80    --  -82.00 -77.00   9.29   51
115  ω    -89.00 -63.50   0.50    0.80    --  -86.25 -77.00  30.00   51
116  ω    -89.00 -63.50   0.50    0.80    --  -86.25 -77.00  90.00   51
117  ω    -86.00 -60.50   0.50    0.80    --  -78.00 -71.00 144.02   51
118  ω    -81.00 -55.50   0.50    0.80    --  -74.00 -66.00 163.42   51
119  ω    -91.00 -65.50   0.50    0.80    --  -86.25 -72.00 127.98   51
120  ω    -92.00 -64.50   0.50    0.80    --  -86.25 -74.00 160.54   55
121  ω    -89.00 -63.50   0.50    0.80    --  -86.25 -77.00 120.00   51
122  ω    -89.00 -63.50   0.50    0.80    --  -86.25 -77.00  60.00   51
123  ω    -89.00 -63.50   0.50    0.80    --  -86.25 -77.00   0.00   51
124  ω    -89.00 -63.00   0.50    0.80    --  -86.25 -80.00 -32.19   52
125  ω    -89.00 -63.50   0.50    0.80    --  -86.25 -77.00 -90.00   51
126  ω    -95.00 -69.50   0.50    0.80    --  -86.25 -62.00 -99.98   51
127  ω    -90.00 -64.00   0.50    0.80    --  -86.25 -77.00-150.00   52
128  ω    -89.00 -63.50   0.50    0.80    --  -86.25 -77.00-180.00   51
129  ω    -97.00 -67.00   0.50    0.80    --  -86.25 -75.00-115.04   60
130  ω    -90.00 -64.50   0.50    0.80    --  -86.25 -75.00 -48.11   51
131  ω    -87.00 -62.50   0.50    0.80    --  -86.25 -80.00-133.45   49
132  ω   -108.00 -68.50   0.50    0.20    --  -48.29-133.00  -5.00   79
133  ω   -118.00 -92.50   0.50    0.20    --  -48.29-136.00 176.00   51
134  ω   -136.00-111.50   0.50    0.80    --  -86.25-136.00 176.00   49
135  ω   -146.00 -60.50   0.50    0.80    --  -78.00 -64.00  14.83  171
136  ω   -137.00-112.50   0.50    0.80    --  -86.25-133.00  -5.00   49
137  ω   -133.00 -67.50   0.50    0.80    --  -86.25 -67.00 -29.04  131
138  ω   -135.00-109.00   0.50    0.20    --  -66.00 -79.00-172.51   52
139  ω   -159.00-133.00   0.50    0.80    --  -86.25 -77.00-150.00   52
;
_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      -0.0497419000
_diffrn_orient_matrix_UB_12      -0.0803104000
_diffrn_orient_matrix_UB_13      0.0387930000
_diffrn_orient_matrix_UB_21      0.0952264000
_diffrn_orient_matrix_UB_22      -0.0439613000
_diffrn_orient_matrix_UB_23      -0.0667708000
_diffrn_orient_matrix_UB_31      0.1402940000
_diffrn_orient_matrix_UB_32      0.0013488000
_diffrn_orient_matrix_UB_33      0.1313434000
_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  0.1170
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            56280
_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         77.336
_diffrn_reflns_theta_min         5.104
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.204
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0655
_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)+(0.2000P)²+1.2500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1908
_refine_ls_wR_factor_ref         0.2959
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2879
_reflns_number_total             3363
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj01423a2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7062618--7062620.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7062619
_shelx_shelxl_version_number     2017/1
_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_min   0.810
_shelx_estimated_absorpt_t_max   0.898
_oxdiff_exptl_absorpt_empirical_full_min 0.596
_oxdiff_exptl_absorpt_empirical_full_max 2.526
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_oxdiff_digest_frames
;
0182ab7078d715560ade0a0830909ca45c0003686e3
;
_diffrn_oxdiff_digest_hkl
;
01b80112dee8ee39c9738f5fea6c80a777c7c6
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Cl1 Cl -0.19708(12) 0.47008(6) 0.23003(9) 0.0703(4) Uani 1 1 d . . . . .
O1 O 0.3735(2) 0.37284(12) 0.92772(19) 0.0395(5) Uani 1 1 d . . . . .
O2 O 0.4714(3) 0.24235(14) 0.5875(2) 0.0527(6) Uani 1 1 d . . . . .
N2 N 0.2122(3) 0.33091(18) 1.0192(3) 0.0453(6) Uani 1 1 d . . . . .
C8 C 0.3999(3) 0.31468(16) 0.7387(3) 0.0352(6) Uani 1 1 d . . . . .
C4 C 0.1278(3) 0.32815(16) 0.5740(3) 0.0367(6) Uani 1 1 d . . . . .
C14 C 0.2534(3) 0.32256(16) 0.9152(3) 0.0352(6) Uani 1 1 d . . . . .
C13 C 0.4530(3) 0.36039(16) 0.8468(3) 0.0347(6) Uani 1 1 d . . . . .
C7 C 0.2395(3) 0.27992(16) 0.6899(3) 0.0353(6) Uani 1 1 d . . . . .
H7 H 0.244119 0.225703 0.658840 0.042 Uiso 1 1 calc R U . . .
C15 C 0.1919(3) 0.27530(17) 0.8081(3) 0.0372(6) Uani 1 1 d . . . . .
C9 C 0.5066(3) 0.29275(17) 0.6746(3) 0.0405(6) Uani 1 1 d . . . . .
N1 N -0.0235(4) 0.17880(19) 0.7986(3) 0.0610(8) Uani 1 1 d . . . . .
C16 C 0.0739(3) 0.22132(18) 0.8043(3) 0.0431(7) Uani 1 1 d . . . . .
C11 C 0.6708(3) 0.41211(18) 0.7893(3) 0.0434(7) Uani 1 1 d . . . . .
C12 C 0.6017(3) 0.40362(19) 0.8959(3) 0.0438(7) Uani 1 1 d . . . . .
H12A H 0.673629 0.375357 0.971236 0.053 Uiso 1 1 calc R U . . .
H12B H 0.586360 0.456076 0.925704 0.053 Uiso 1 1 calc R U . . .
C1 C -0.0732(4) 0.41515(18) 0.3617(3) 0.0465(7) Uani 1 1 d . . . . .
C10 C 0.6636(4) 0.33014(19) 0.7259(4) 0.0495(8) Uani 1 1 d . . . . .
H10A H 0.698589 0.335157 0.653236 0.059 Uiso 1 1 calc R U . . .
H10B H 0.734011 0.294805 0.790845 0.059 Uiso 1 1 calc R U . . .
C3 C -0.0064(3) 0.3600(2) 0.5774(3) 0.0466(7) Uani 1 1 d . . . . .
H3 H -0.029618 0.352180 0.652130 0.056 Uiso 1 1 calc R U . . .
C5 C 0.1597(4) 0.3416(2) 0.4602(3) 0.0489(7) Uani 1 1 d . . . . .
H5 H 0.249227 0.321030 0.455539 0.059 Uiso 1 1 calc R U . . .
C6 C 0.0605(5) 0.3848(2) 0.3547(3) 0.0544(8) Uani 1 1 d . . . . .
H6 H 0.083370 0.393295 0.279941 0.065 Uiso 1 1 calc R U . . .
C2 C -0.1071(4) 0.4032(2) 0.4724(4) 0.0540(8) Uani 1 1 d . . . . .
H2 H -0.196711 0.423838 0.476816 0.065 Uiso 1 1 calc R U . . .
C18 C 0.8383(4) 0.4399(3) 0.8562(4) 0.0622(10) Uani 1 1 d . . . . .
H18A H 0.883944 0.443740 0.791193 0.093 Uiso 1 1 calc R U . . .
H18B H 0.894542 0.402258 0.922975 0.093 Uiso 1 1 calc R U . . .
H18C H 0.840858 0.490971 0.896137 0.093 Uiso 1 1 calc R U . . .
C17 C 0.5811(5) 0.4720(2) 0.6834(4) 0.0617(10) Uani 1 1 d . . . . .
H17A H 0.581360 0.522669 0.723890 0.093 Uiso 1 1 calc R U . . .
H17B H 0.477297 0.453907 0.640253 0.093 Uiso 1 1 calc R U . . .
H17C H 0.628071 0.477019 0.619531 0.093 Uiso 1 1 calc R U . . .
H1N H 0.138(5) 0.301(2) 1.027(4) 0.050(10) Uiso 1 1 d . . . . .
H2N H 0.282(6) 0.347(3) 1.088(5) 0.065(13) Uiso 1 1 d . . . . .
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'
Cl Cl 0.3639 0.7018 '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
C13 O1 C14 117.9(2) . . ?
C14 N2 H1N 121(3) . . ?
C14 N2 H2N 114(3) . . ?
H1N N2 H2N 119(4) . . ?
C13 C8 C9 117.9(2) . . ?
C13 C8 C7 121.6(2) . . ?
C9 C8 C7 120.3(2) . . ?
C3 C4 C5 117.6(3) . . ?
C3 C4 C7 122.0(2) . . ?
C5 C4 C7 120.4(3) . . ?
N2 C14 C15 129.0(3) . . ?
N2 C14 O1 109.9(2) . . ?
C15 C14 O1 121.1(2) . . ?
C8 C13 O1 122.8(2) . . ?
C8 C13 C12 126.0(2) . . ?
O1 C13 C12 111.1(2) . . ?
C8 C7 C15 107.1(2) . . ?
C8 C7 C4 111.5(2) . . ?
C15 C7 C4 113.4(2) . . ?
C8 C7 H7 108.2 . . ?
C15 C7 H7 108.2 . . ?
C4 C7 H7 108.2 . . ?
C14 C15 C16 118.5(3) . . ?
C14 C15 C7 122.5(2) . . ?
C16 C15 C7 119.0(3) . . ?
O2 C9 C8 120.7(3) . . ?
O2 C9 C10 121.3(3) . . ?
C8 C9 C10 117.9(3) . . ?
N1 C16 C15 178.3(4) . . ?
C17 C11 C10 109.5(3) . . ?
C17 C11 C18 109.6(3) . . ?
C10 C11 C18 110.5(3) . . ?
C17 C11 C12 111.3(3) . . ?
C10 C11 C12 107.4(2) . . ?
C18 C11 C12 108.6(3) . . ?
C13 C12 C11 112.4(2) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C2 C1 C6 120.6(3) . . ?
C2 C1 Cl1 119.9(3) . . ?
C6 C1 Cl1 119.4(3) . . ?
C9 C10 C11 114.4(2) . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C4 C3 C2 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C1 C6 C5 119.3(3) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
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
Cl1 C1 1.737(3) . ?
O1 C13 1.372(3) . ?
O1 C14 1.377(3) . ?
O2 C9 1.223(4) . ?
N2 C14 1.338(4) . ?
N2 H1N 0.89(4) . ?
N2 H2N 0.83(5) . ?
C8 C13 1.337(4) . ?
C8 C9 1.471(4) . ?
C8 C7 1.516(4) . ?
C4 C3 1.386(4) . ?
C4 C5 1.401(4) . ?
C4 C7 1.537(4) . ?
C14 C15 1.350(4) . ?
C13 C12 1.486(4) . ?
C7 C15 1.518(4) . ?
C7 H7 0.9800 . ?
C15 C16 1.423(4) . ?
C9 C10 1.506(4) . ?
N1 C16 1.146(4) . ?
C11 C17 1.526(5) . ?
C11 C10 1.533(4) . ?
C11 C18 1.539(4) . ?
C11 C12 1.539(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C1 C2 1.377(5) . ?
C1 C6 1.387(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C3 C2 1.385(5) . ?
C3 H3 0.9300 . ?
C5 C6 1.384(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
