#------------------------------------------------------------------------------
#$Date: 2022-05-11 11:10:30 +0300 (Wed, 11 May 2022) $
#$Revision: 275328 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/52/8105215.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_8105215
loop_
_publ_author_name
'Tzvetkov, Nikolay T.'
'Peeva, Martina I.'
'Tsakovska, Ivanka'
'Milella, Luigi'
'Pajeva, Ilza'
'Stammler, Hans-Georg'
_publ_section_title
;
 The crystal structure of
 (4SR)-7-(3,4-dichlorobenzyl)-4,8,8-trimethyl-7,8-dihydroimidazo[5,1c][1,2,4]triazine-3,6(2H,4H)-dione,
 C15H16Cl2N4O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              319
_journal_page_last               321
_journal_paper_doi               10.1515/ncrs-2022-0016
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C15 H16 Cl2 N4 O2'
_chemical_formula_sum            'C15 H16 Cl2 N4 O2'
_chemical_formula_weight         355.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 109.217(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.2014(7)
_cell_length_b                   7.59320(10)
_cell_length_c                   17.9766(4)
_cell_measurement_reflns_used    19598
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      76.3120
_cell_measurement_theta_min      3.5320
_cell_volume                     3377.20(14)
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 [2]'
_computing_publication_material  'Olex2 [2]'
_computing_structure_refinement  'ShelXL [3]'
_computing_structure_solution    'ShelXT [4]'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3114
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -59.00  26.00   1.00   10.00    --  -38.50  37.00 -90.00   85
  2  ω   -116.00 -15.00   1.00   10.00    --  -38.50 -19.00 -90.00  101
  3  ω    -59.00  33.00   1.00   10.00    --  -38.50  37.00  90.00   92
  4  ω    -84.00  -7.00   1.00   10.00    --  -38.50 125.00 -90.00   77
  5  ω     11.00  36.00   1.00   10.00    --   42.70  81.00-122.15   25
  6  ω     51.00 111.00   1.00   10.00    --   42.70  57.00 150.00   60
  7  ω     12.00  38.00   1.00   10.00    --   42.70  78.00 173.10   26
  8  ω     12.00  42.00   1.00   10.00    --   42.70  79.00   9.45   30
  9  ω     13.00  40.00   1.00   10.00    --   42.70  77.00  93.43   27
 10  ω     18.00  68.00   1.00   10.00    --   42.70  57.00  90.00   50
 11  ω     18.00  46.00   1.00   10.00    --   42.70  57.00 150.00   28
 12  ω     12.00  38.00   1.00   10.00    --   42.70  82.00 -43.45   26
 13  ω     16.00  70.00   1.00   10.00    --   42.70  67.00 -65.12   54
 14  ω     75.00 105.00   1.00   10.00    --   42.70  57.00  90.00   30
 15  ω     12.00  80.00   1.00   10.00    --   42.70 -99.00 150.00   68
 16  ω     18.00  68.00   1.00   10.00    --   42.70  57.00-120.00   50
 17  ω     85.00 114.00   1.00   10.00    --   42.70  37.00  60.00   29
 18  ω     23.00  76.00   1.00   10.00    --   42.70  37.00  60.00   53
 19  ω     85.00 120.00   1.00   40.00    --  111.00  61.00  90.00   35
 20  ω     32.00 107.00   1.00   40.00    --  111.00 -94.00  30.00   75
 21  ω     85.00 111.00   1.00   40.00    --  111.00  61.00 -65.34   26
 22  ω     89.00 124.00   1.00   40.00    --  111.00  45.00 -90.00   35
 23  ω     85.00 125.00   1.00   40.00    --  111.00  61.00 120.00   40
 24  ω     89.00 124.00   1.00   40.00    --  111.00  45.00 -60.00   35
 25  ω     85.00 111.00   1.00   40.00    --  111.00  61.00-159.21   26
 26  ω     44.00 133.00   1.00   40.00    --  111.00 -61.00  30.00   89
 27  ω     85.00 111.00   1.00   40.00    --  111.00  61.00   0.00   26
 28  ω     85.00 111.00   1.00   40.00    --  111.00  61.00  60.00   26
 29  ω    152.00 178.00   1.00   40.00    --  111.00  61.00  60.00   26
 30  ω     85.00 168.00   1.00   40.00    --  111.00  62.00 140.30   83
 31  ω     63.00 136.00   1.00   40.00    --  111.00 -61.00-150.00   73
 32  ω     89.00 144.00   1.00   40.00    --  111.00  45.00-180.00   55
 33  ω     89.00 115.00   1.00   40.00    --  111.00  45.00 120.00   26
 34  ω     85.00 111.00   1.00   40.00    --  111.00  61.00 -90.00   26
 35  ω     85.00 177.00   1.00   40.00    --  111.00  61.00-180.00   92
 36  ω    144.00 174.00   1.00   40.00    --  111.00  51.00  56.39   30
 37  ω     90.00 171.00   1.00   40.00    --  111.00  45.00   0.00   81
 38  ω    133.00 178.00   1.00   40.00    --  111.00  61.00-120.00   45
 39  ω     85.00 110.00   1.00   40.00    --  111.00  61.00-120.00   25
 40  ω    134.00 176.00   1.00   40.00    --  111.00  61.00 -90.00   42
 41  ω     85.00 113.00   1.00   40.00    --  111.00  61.00 150.00   28
 42  ω     89.00 123.00   1.00   40.00    --  111.00  45.00  90.00   34
 43  ω     86.00 115.00   1.00   40.00    --  111.00  58.00  16.31   29
 44  ω    132.00 178.00   1.00   40.00    --  111.00  61.00-150.00   46
 45  ω     41.00 112.00   1.00   40.00    --  111.00-125.00-150.00   71
 46  ω     41.00 113.00   1.00   40.00    --  111.00-125.00  30.00   72
 47  ω     85.00 111.00   1.00   40.00    --  111.00  61.00-150.00   26
 48  ω     85.00 111.00   1.00   40.00    --  111.00  61.00 -30.00   26
 49  ω     32.00 107.00   1.00   40.00    --  111.00 -94.00-120.00   75
 50  ω     89.00 122.00   1.00   40.00    --  111.00  45.00-120.00   33
 51  ω     89.00 155.00   1.00   40.00    --  111.00  45.00 -30.00   66
 52  ω     85.00 178.00   1.00   40.00    --  111.00  61.00  30.00   93
 53  ω    127.00 175.00   1.00   40.00    --  111.00  61.00  90.00   48
 54  ω    131.00 156.00   1.00   40.00    --  111.00  61.00 -65.34   25
 55  ω     41.00 112.00   1.00   40.00    --  111.00-125.00-120.00   71
 56  ω     87.00 113.00   1.00   40.00    --  111.00  51.00  56.39   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       'CrysAlisPro convention [1]'
_diffrn_orient_matrix_UB_11      0.0053441000
_diffrn_orient_matrix_UB_12      0.1917497000
_diffrn_orient_matrix_UB_13      -0.0245162000
_diffrn_orient_matrix_UB_21      0.0126618000
_diffrn_orient_matrix_UB_22      0.0595368000
_diffrn_orient_matrix_UB_23      0.0861107000
_diffrn_orient_matrix_UB_31      0.0607142000
_diffrn_orient_matrix_UB_32      -0.0292668000
_diffrn_orient_matrix_UB_33      0.0147942000
_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  0.0443
_diffrn_reflns_av_unetI/netI     0.0820
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            51349
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.396
_diffrn_reflns_theta_min         3.573
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.586
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.678
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
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_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       plate
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.172
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.023
_exptl_crystal_size_rad          0.104
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         8782
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      149.487
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0503
_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)+(0.0935P)²+0.2462P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1411
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7282
_reflns_number_total             8782
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0016_suppl.cif
_cod_data_source_block           ntz
_cod_database_code               8105215
_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   0.922
_shelx_estimated_absorpt_t_min   0.577
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6481(13)
 0.3519(13)
2. 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
3. Uiso/Uaniso restraints and constraints
C2 \\sim C5: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 1*[Sof(Cl1)+Sof(Cl3)+Sof(H13)+Sof(H15)+Sof(Cl21)+Sof(cl23)+Sof(H33)+Sof(H35)]=
 2 with esd of 0
 Sof(Cl3)=Sof(H13)=Sof(cl23)=Sof(H33)=1-FVAR(1)
 Sof(Cl1)=Sof(H15)=Sof(Cl21)=Sof(H35)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C2(H2A), C22(H22A)
5.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C30(H30A,H30B)
5.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C12(H12), C13(H13), C15(H15), C16(H16), N22(H22), C32(H32), C33(H33),
 C35(H35), C36(H36)
5.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C25(H25A,H25B,H25C),
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.24064(6) 0.8803(2) 0.54017(9) 0.0601(4) Uani 0.670(2) 1 d . . P A 1
Cl2 Cl 0.20413(4) 0.90910(16) 0.34773(7) 0.0618(3) Uani 1 1 d . . . . .
Cl3 Cl 0.28647(10) 0.7416(4) 0.25871(12) 0.0443(7) Uani 0.330(2) 1 d . . P A 2
O1 O 0.44535(10) 0.0447(3) 0.86184(11) 0.0312(4) Uani 1 1 d . . . . .
O2 O 0.44157(10) 0.6376(2) 0.70472(12) 0.0339(5) Uani 1 1 d . . . . .
N1 N 0.42112(10) 0.0409(3) 0.65427(12) 0.0232(4) Uani 1 1 d . . . . .
N2 N 0.42767(10) -0.0051(3) 0.73251(12) 0.0230(4) Uani 1 1 d . . . . .
H2 H 0.424750 -0.117917 0.741555 0.028 Uiso 1 1 calc R . . . .
N3 N 0.42918(9) 0.3351(3) 0.69885(11) 0.0197(4) Uani 1 1 d . . . . .
N4 N 0.42162(9) 0.4782(3) 0.58863(12) 0.0207(4) Uani 1 1 d . . . . .
C1 C 0.43787(12) 0.1021(3) 0.79549(15) 0.0233(5) Uani 1 1 d . . . . .
C2 C 0.44052(15) 0.3005(3) 0.78324(15) 0.0312(6) Uani 1 1 d . U . . .
H2A H 0.478422 0.339455 0.811589 0.037 Uiso 1 1 calc R . . . .
C3 C 0.42210(10) 0.2057(3) 0.64346(13) 0.0190(5) Uani 1 1 d . . . . .
C5 C 0.4042(2) 0.3985(5) 0.8177(2) 0.0532(11) Uani 1 1 d . U . . .
H5A H 0.405546 0.524576 0.806851 0.080 Uiso 1 1 calc GR . . . .
H5B H 0.416149 0.379461 0.874826 0.080 Uiso 1 1 calc GR . . . .
H5C H 0.367050 0.355768 0.794188 0.080 Uiso 1 1 calc GR . . . .
C6 C 0.43151(11) 0.4997(3) 0.66679(14) 0.0223(5) Uani 1 1 d . . . . .
C7 C 0.41816(11) 0.2906(3) 0.56517(14) 0.0206(5) Uani 1 1 d . . . . .
C8 C 0.46718(12) 0.2348(4) 0.54158(15) 0.0257(5) Uani 1 1 d . . . . .
H8A H 0.466340 0.296842 0.493392 0.039 Uiso 1 1 calc GR . . . .
H8B H 0.465855 0.107456 0.532216 0.039 Uiso 1 1 calc GR . . . .
H8C H 0.500565 0.264517 0.584107 0.039 Uiso 1 1 calc GR . . . .
C9 C 0.36532(12) 0.2479(4) 0.50024(16) 0.0289(6) Uani 1 1 d . . . . .
H9A H 0.334832 0.285889 0.516487 0.043 Uiso 1 1 calc GR . . . .
H9B H 0.362981 0.120590 0.490631 0.043 Uiso 1 1 calc GR . . . .
H9C H 0.364153 0.309595 0.451837 0.043 Uiso 1 1 calc GR . . . .
C10 C 0.42311(11) 0.6247(3) 0.53679(15) 0.0241(5) Uani 1 1 d . . . . .
H10A H 0.441900 0.585872 0.500031 0.029 Uiso 1 1 calc R . . . .
H10B H 0.444481 0.721855 0.569064 0.029 Uiso 1 1 calc R . . . .
C11 C 0.36803(11) 0.6939(3) 0.48958(15) 0.0229(5) Uani 1 1 d . . . . .
C12 C 0.33246(12) 0.7516(4) 0.52757(16) 0.0273(5) Uani 1 1 d . . . . .
H12 H 0.342715 0.745747 0.583353 0.033 Uiso 1 1 calc R . . . .
C13 C 0.28240(13) 0.8172(4) 0.4842(2) 0.0356(6) Uani 1 1 d . . . . .
H13 H 0.258358 0.857075 0.510283 0.043 Uiso 0.330(2) 1 calc R . P A 2
C14 C 0.26701(13) 0.8252(4) 0.4026(2) 0.0387(7) Uani 1 1 d . . . . .
C15 C 0.30212(14) 0.7692(6) 0.36474(19) 0.0434(8) Uani 1 1 d . . . . .
H15 H 0.291907 0.776254 0.308987 0.052 Uiso 0.670(2) 1 calc R . P A 1
C16 C 0.35204(13) 0.7031(4) 0.40802(17) 0.0331(6) Uani 1 1 d . . . . .
H16 H 0.375880 0.663203 0.381616 0.040 Uiso 1 1 calc R . . . .
Cl21 Cl 0.20841(6) 0.1885(3) -0.03351(8) 0.0585(4) Uani 0.670(2) 1 d . . P A 1
Cl22 Cl 0.29098(4) 0.0819(2) 0.13548(7) 0.0710(3) Uani 1 1 d . . . . .
Cl24 Cl 0.27097(9) 0.2646(4) 0.29263(13) 0.0441(7) Uani 0.330(2) 1 d . . P A 2
O21 O 0.05460(9) 0.9722(2) 0.41383(11) 0.0274(4) Uani 1 1 d . . . . .
O22 O 0.05551(9) 0.3798(2) 0.26042(11) 0.0276(4) Uani 1 1 d . . . . .
N21 N 0.07745(9) 0.9750(3) 0.22835(12) 0.0200(4) Uani 1 1 d . . . . .
N22 N 0.07060(9) 1.0221(3) 0.30005(12) 0.0196(4) Uani 1 1 d . . . . .
H22 H 0.071980 1.135487 0.310705 0.024 Uiso 1 1 calc R . . . .
N23 N 0.06836(9) 0.6815(2) 0.26527(12) 0.0187(4) Uani 1 1 d . . . . .
N24 N 0.07511(9) 0.5362(3) 0.16239(12) 0.0208(4) Uani 1 1 d . . . . .
C21 C 0.06214(10) 0.9141(3) 0.35464(13) 0.0194(5) Uani 1 1 d . . . . .
C22 C 0.06107(12) 0.7159(3) 0.34149(14) 0.0241(5) Uani 1 1 d . . . . .
H22A H 0.024752 0.670534 0.339216 0.029 Uiso 1 1 calc R . . . .
C23 C 0.07601(10) 0.8096(3) 0.21674(13) 0.0178(4) Uani 1 1 d . . . . .
C25 C 0.10347(15) 0.6249(4) 0.40855(17) 0.0362(7) Uani 1 1 d . . . . .
H25A H 0.101788 0.497557 0.399094 0.054 Uiso 1 1 calc GR . . . .
H25B H 0.096774 0.649356 0.458058 0.054 Uiso 1 1 calc GR . . . .
H25C H 0.139361 0.668682 0.411983 0.054 Uiso 1 1 calc GR . . . .
C26 C 0.06558(11) 0.5152(3) 0.23124(14) 0.0199(5) Uani 1 1 d . . . . .
C27 C 0.08086(11) 0.7232(3) 0.14327(14) 0.0210(5) Uani 1 1 d . . . . .
C28 C 0.03465(12) 0.7830(3) 0.07122(14) 0.0262(5) Uani 1 1 d . . . . .
H28A H 0.037428 0.724005 0.024214 0.039 Uiso 1 1 calc GR . . . .
H28B H 0.036674 0.910765 0.065095 0.039 Uiso 1 1 calc GR . . . .
H28C H 0.000080 0.752614 0.077968 0.039 Uiso 1 1 calc GR . . . .
C29 C 0.13579(12) 0.7594(4) 0.13373(16) 0.0274(5) Uani 1 1 d . . . . .
H29A H 0.164632 0.720584 0.181144 0.041 Uiso 1 1 calc GR . . . .
H29B H 0.139521 0.885887 0.126022 0.041 Uiso 1 1 calc GR . . . .
H29C H 0.138408 0.694855 0.087914 0.041 Uiso 1 1 calc GR . . . .
C30 C 0.07418(11) 0.3899(3) 0.10984(14) 0.0221(5) Uani 1 1 d . . . . .
H30A H 0.056105 0.428730 0.054858 0.026 Uiso 1 1 calc R . . . .
H30B H 0.052269 0.293496 0.120934 0.026 Uiso 1 1 calc R . . . .
C31 C 0.12956(11) 0.3184(3) 0.11694(15) 0.0216(5) Uani 1 1 d . . . . .
C32 C 0.14193(13) 0.2777(4) 0.05010(18) 0.0342(6) Uani 1 1 d . . . . .
H32 H 0.116201 0.300355 -0.000279 0.041 Uiso 1 1 calc R . . . .
C33 C 0.19119(14) 0.2046(5) 0.0555(2) 0.0432(8) Uani 1 1 d . . . . .
H33 H 0.198910 0.174851 0.008941 0.052 Uiso 0.330(2) 1 calc R . P A 2
C34 C 0.22937(13) 0.1745(5) 0.1285(2) 0.0385(7) Uani 1 1 d . . . . .
C35 C 0.21756(15) 0.2155(7) 0.1953(2) 0.0534(10) Uani 1 1 d . . . . .
H35 H 0.243745 0.195419 0.245533 0.064 Uiso 0.670(2) 1 calc R . P A 1
C36 C 0.16758(13) 0.2861(6) 0.18997(19) 0.0429(8) Uani 1 1 d . . . . .
H36 H 0.159494 0.312315 0.236556 0.052 Uiso 1 1 calc R . . . .
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 0 11 0.0164
3 0 -11 0.0066
0 1 0 0.0760
0 -1 0 0.0927
1 0 0 0.0267
-1 0 0 0.0354
14 -3 0 0.0359
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
C3 N1 N2 113.4(2) . .
N1 N2 H2 116.0 . .
C1 N2 N1 128.1(2) . .
C1 N2 H2 116.0 . .
C3 N3 C2 123.8(2) . .
C3 N3 C6 111.04(19) . .
C6 N3 C2 124.6(2) . .
C6 N4 C7 112.65(19) . .
C6 N4 C10 122.3(2) . .
C10 N4 C7 124.3(2) . .
O1 C1 N2 121.9(2) . .
O1 C1 C2 119.4(2) . .
N2 C1 C2 118.7(2) . .
N3 C2 C1 108.8(2) . .
N3 C2 H2A 107.6 . .
N3 C2 C5 113.5(3) . .
C1 C2 H2A 107.6 . .
C5 C2 C1 111.5(3) . .
C5 C2 H2A 107.6 . .
N1 C3 N3 127.0(2) . .
N1 C3 C7 124.2(2) . .
N3 C3 C7 108.73(19) . .
C2 C5 H5A 109.5 . .
C2 C5 H5B 109.5 . .
C2 C5 H5C 109.5 . .
H5A C5 H5B 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
O2 C6 N3 124.6(2) . .
O2 C6 N4 127.7(2) . .
N4 C6 N3 107.7(2) . .
N4 C7 C3 99.51(18) . .
N4 C7 C8 111.4(2) . .
N4 C7 C9 112.2(2) . .
C3 C7 C8 109.3(2) . .
C3 C7 C9 112.8(2) . .
C9 C7 C8 111.2(2) . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C7 C9 H9A 109.5 . .
C7 C9 H9B 109.5 . .
C7 C9 H9C 109.5 . .
H9A C9 H9B 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
N4 C10 H10A 108.8 . .
N4 C10 H10B 108.8 . .
N4 C10 C11 113.8(2) . .
H10A C10 H10B 107.7 . .
C11 C10 H10A 108.8 . .
C11 C10 H10B 108.8 . .
C12 C11 C10 120.3(2) . .
C16 C11 C10 120.8(3) . .
C16 C11 C12 118.9(3) . .
C11 C12 H12 120.0 . .
C13 C12 C11 120.1(3) . .
C13 C12 H12 120.0 . .
C12 C13 Cl1 115.2(2) . .
C12 C13 H13 119.9 . .
C12 C13 C14 120.3(3) . .
C14 C13 Cl1 124.5(3) . .
C14 C13 H13 119.9 . .
C13 C14 Cl2 120.5(3) . .
C15 C14 Cl2 119.6(3) . .
C15 C14 C13 119.9(3) . .
C14 C15 Cl3 126.4(3) . .
C14 C15 H15 120.1 . .
C16 C15 Cl3 113.1(3) . .
C16 C15 C14 119.8(3) . .
C16 C15 H15 120.1 . .
C11 C16 H16 119.5 . .
C15 C16 C11 121.0(3) . .
C15 C16 H16 119.5 . .
C23 N21 N22 113.33(19) . .
N21 N22 H22 116.1 . .
C21 N22 N21 127.78(19) . .
C21 N22 H22 116.1 . .
C23 N23 C22 124.16(19) . .
C23 N23 C26 111.25(19) . .
C26 N23 C22 124.5(2) . .
C26 N24 C27 112.95(19) . .
C26 N24 C30 122.5(2) . .
C30 N24 C27 124.3(2) . .
O21 C21 N22 121.6(2) . .
O21 C21 C22 119.4(2) . .
N22 C21 C22 119.1(2) . .
N23 C22 C21 108.62(19) . .
N23 C22 H22A 108.4 . .
N23 C22 C25 112.1(2) . .
C21 C22 H22A 108.4 . .
C25 C22 C21 110.9(2) . .
C25 C22 H22A 108.4 . .
N21 C23 N23 127.0(2) . .
N21 C23 C27 124.3(2) . .
N23 C23 C27 108.68(19) . .
C22 C25 H25A 109.5 . .
C22 C25 H25B 109.5 . .
C22 C25 H25C 109.5 . .
H25A C25 H25B 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
O22 C26 N23 124.1(2) . .
O22 C26 N24 128.6(2) . .
N24 C26 N23 107.2(2) . .
N24 C27 C23 99.70(18) . .
N24 C27 C28 111.7(2) . .
N24 C27 C29 111.7(2) . .
C23 C27 C28 109.9(2) . .
C23 C27 C29 111.8(2) . .
C28 C27 C29 111.4(2) . .
C27 C28 H28A 109.5 . .
C27 C28 H28B 109.5 . .
C27 C28 H28C 109.5 . .
H28A C28 H28B 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
C27 C29 H29A 109.5 . .
C27 C29 H29B 109.5 . .
C27 C29 H29C 109.5 . .
H29A C29 H29B 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
N24 C30 H30A 108.7 . .
N24 C30 H30B 108.7 . .
N24 C30 C31 114.1(2) . .
H30A C30 H30B 107.6 . .
C31 C30 H30A 108.7 . .
C31 C30 H30B 108.7 . .
C32 C31 C30 120.0(2) . .
C32 C31 C36 119.0(3) . .
C36 C31 C30 120.9(2) . .
C31 C32 H32 119.6 . .
C31 C32 C33 120.8(3) . .
C33 C32 H32 119.6 . .
C32 C33 Cl21 117.8(3) . .
C32 C33 H33 120.0 . .
C32 C33 C34 120.0(3) . .
C34 C33 Cl21 121.2(3) . .
C34 C33 H33 120.0 . .
C33 C34 Cl22 120.1(3) . .
C35 C34 Cl22 120.3(3) . .
C35 C34 C33 119.5(3) . .
C34 C35 Cl24 123.1(3) . .
C34 C35 H35 119.8 . .
C34 C35 C36 120.5(3) . .
C36 C35 Cl24 112.5(3) . .
C36 C35 H35 119.8 . .
C31 C36 C35 120.1(3) . .
C31 C36 H36 120.0 . .
C35 C36 H36 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C13 1.779(4) .
Cl2 C14 1.739(3) .
Cl3 C15 1.825(4) .
O1 C1 1.224(3) .
O2 C6 1.230(3) .
N1 N2 1.404(3) .
N1 C3 1.268(3) .
N2 H2 0.8800 .
N2 C1 1.348(3) .
N3 C2 1.470(3) .
N3 C3 1.368(3) .
N3 C6 1.386(3) .
N4 C6 1.352(3) .
N4 C7 1.480(3) .
N4 C10 1.460(3) .
C1 C2 1.528(4) .
C2 H2A 1.0000 .
C2 C5 1.494(4) .
C3 C7 1.520(3) .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C7 C8 1.539(4) .
C7 C9 1.523(4) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C10 C11 1.508(4) .
C11 C12 1.395(4) .
C11 C16 1.388(4) .
C12 H12 0.9500 .
C12 C13 1.379(4) .
C13 H13 0.9500 .
C13 C14 1.388(5) .
C14 C15 1.380(5) .
C15 H15 0.9500 .
C15 C16 1.378(5) .
C16 H16 0.9500 .
Cl21 C33 1.803(4) .
Cl22 C34 1.727(3) .
Cl24 C35 1.884(4) .
O21 C21 1.226(3) .
O22 C26 1.222(3) .
N21 N22 1.405(3) .
N21 C23 1.272(3) .
N22 H22 0.8800 .
N22 C21 1.352(3) .
N23 C22 1.468(3) .
N23 C23 1.365(3) .
N23 C26 1.394(3) .
N24 C26 1.350(3) .
N24 C27 1.480(3) .
N24 C30 1.454(3) .
C21 C22 1.523(3) .
C22 H22A 1.0000 .
C22 C25 1.511(4) .
C23 C27 1.517(3) .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C27 C28 1.522(4) .
C27 C29 1.529(4) .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
C29 H29A 0.9800 .
C29 H29B 0.9800 .
C29 H29C 0.9800 .
C30 H30A 0.9900 .
C30 H30B 0.9900 .
C30 C31 1.515(4) .
C31 C32 1.379(4) .
C31 C36 1.384(4) .
C32 H32 0.9500 .
C32 C33 1.379(4) .
C33 H33 0.9500 .
C33 C34 1.383(5) .
C34 C35 1.369(5) .
C35 H35 0.9500 .
C35 C36 1.389(5) .
C36 H36 0.9500 .
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
Cl1 C13 C14 Cl2 2.6(4) . . . .
Cl1 C13 C14 C15 -178.5(3) . . . .
Cl2 C14 C15 Cl3 -9.9(5) . . . .
Cl2 C14 C15 C16 179.8(3) . . . .
Cl3 C15 C16 C11 -172.4(3) . . . .
O1 C1 C2 N3 -178.9(3) . . . .
O1 C1 C2 C5 -53.0(4) . . . .
N1 N2 C1 O1 -176.4(3) . . . .
N1 N2 C1 C2 3.1(4) . . . .
N1 C3 C7 N4 -179.8(3) . . . .
N1 C3 C7 C8 -63.1(3) . . . .
N1 C3 C7 C9 61.1(4) . . . .
N2 N1 C3 N3 0.7(4) . . . .
N2 N1 C3 C7 177.5(2) . . . .
N2 C1 C2 N3 1.5(4) . . . .
N2 C1 C2 C5 127.4(3) . . . .
N3 C3 C7 N4 -2.5(3) . . . .
N3 C3 C7 C8 114.2(2) . . . .
N3 C3 C7 C9 -121.6(2) . . . .
N4 C10 C11 C12 56.3(3) . . . .
N4 C10 C11 C16 -124.4(3) . . . .
C2 N3 C3 N1 4.1(5) . . . .
C2 N3 C3 C7 -173.1(3) . . . .
C2 N3 C6 O2 -2.6(5) . . . .
C2 N3 C6 N4 176.6(3) . . . .
C3 N1 N2 C1 -4.5(4) . . . .
C3 N3 C2 C1 -4.9(4) . . . .
C3 N3 C2 C5 -129.6(3) . . . .
C3 N3 C6 O2 -174.4(3) . . . .
C3 N3 C6 N4 4.8(3) . . . .
C6 N3 C2 C1 -175.7(2) . . . .
C6 N3 C2 C5 59.6(4) . . . .
C6 N3 C3 N1 176.1(3) . . . .
C6 N3 C3 C7 -1.1(3) . . . .
C6 N4 C7 C3 5.6(3) . . . .
C6 N4 C7 C8 -109.5(2) . . . .
C6 N4 C7 C9 125.1(2) . . . .
C6 N4 C10 C11 -101.0(3) . . . .
C7 N4 C6 O2 172.5(3) . . . .
C7 N4 C6 N3 -6.7(3) . . . .
C7 N4 C10 C11 89.3(3) . . . .
C10 N4 C6 O2 1.7(5) . . . .
C10 N4 C6 N3 -177.5(2) . . . .
C10 N4 C7 C3 176.2(2) . . . .
C10 N4 C7 C8 61.1(3) . . . .
C10 N4 C7 C9 -64.3(3) . . . .
C10 C11 C12 C13 179.0(2) . . . .
C10 C11 C16 C15 -178.8(3) . . . .
C11 C12 C13 Cl1 178.4(2) . . . .
C11 C12 C13 C14 0.4(4) . . . .
C12 C11 C16 C15 0.5(5) . . . .
C12 C13 C14 Cl2 -179.6(2) . . . .
C12 C13 C14 C15 -0.7(5) . . . .
C13 C14 C15 Cl3 171.2(3) . . . .
C13 C14 C15 C16 1.0(6) . . . .
C14 C15 C16 C11 -0.9(6) . . . .
C16 C11 C12 C13 -0.3(4) . . . .
Cl21 C33 C34 Cl22 -11.9(5) . . . .
Cl21 C33 C34 C35 169.4(3) . . . .
Cl22 C34 C35 Cl24 25.6(5) . . . .
Cl22 C34 C35 C36 -178.5(3) . . . .
Cl24 C35 C36 C31 157.3(3) . . . .
O21 C21 C22 N23 177.2(2) . . . .
O21 C21 C22 C25 -59.2(4) . . . .
N21 N22 C21 O21 -177.1(2) . . . .
N21 N22 C21 C22 2.0(4) . . . .
N21 C23 C27 N24 -178.7(2) . . . .
N21 C23 C27 C28 -61.2(3) . . . .
N21 C23 C27 C29 63.1(3) . . . .
N22 N21 C23 N23 0.5(4) . . . .
N22 N21 C23 C27 178.4(2) . . . .
N22 C21 C22 N23 -1.9(4) . . . .
N22 C21 C22 C25 121.8(3) . . . .
N23 C23 C27 N24 -0.5(3) . . . .
N23 C23 C27 C28 117.0(2) . . . .
N23 C23 C27 C29 -118.7(2) . . . .
N24 C30 C31 C32 -136.7(3) . . . .
N24 C30 C31 C36 46.0(4) . . . .
C22 N23 C23 N21 -0.9(4) . . . .
C22 N23 C23 C27 -179.0(2) . . . .
C22 N23 C26 O22 1.7(4) . . . .
C22 N23 C26 N24 -179.1(2) . . . .
C23 N21 N22 C21 -1.1(4) . . . .
C23 N23 C22 C21 1.4(4) . . . .
C23 N23 C22 C25 -121.5(3) . . . .
C23 N23 C26 O22 -175.1(3) . . . .
C23 N23 C26 N24 4.0(3) . . . .
C26 N23 C22 C21 -175.1(2) . . . .
C26 N23 C22 C25 62.0(4) . . . .
C26 N23 C23 N21 176.0(2) . . . .
C26 N23 C23 C27 -2.1(3) . . . .
C26 N24 C27 C23 3.0(3) . . . .
C26 N24 C27 C28 -113.1(2) . . . .
C26 N24 C27 C29 121.3(2) . . . .
C26 N24 C30 C31 -99.1(3) . . . .
C27 N24 C26 O22 174.7(3) . . . .
C27 N24 C26 N23 -4.4(3) . . . .
C27 N24 C30 C31 87.3(3) . . . .
C30 N24 C26 O22 0.5(4) . . . .
C30 N24 C26 N23 -178.6(2) . . . .
C30 N24 C27 C23 177.1(2) . . . .
C30 N24 C27 C28 61.0(3) . . . .
C30 N24 C27 C29 -64.6(3) . . . .
C30 C31 C32 C33 -176.8(3) . . . .
C30 C31 C36 C35 178.0(3) . . . .
C31 C32 C33 Cl21 -170.2(3) . . . .
C31 C32 C33 C34 -1.4(6) . . . .
C32 C31 C36 C35 0.7(6) . . . .
C32 C33 C34 Cl22 179.7(3) . . . .
C32 C33 C34 C35 1.0(6) . . . .
C33 C34 C35 Cl24 -155.7(3) . . . .
C33 C34 C35 C36 0.2(7) . . . .
C34 C35 C36 C31 -1.1(7) . . . .
C36 C31 C32 C33 0.5(5) . . . .
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.1621 -0.4399 11.4957 -0.3831 0.9237 -0.0090
3.1621 0.4399 -11.4957 0.3831 -0.9237 0.0090
0.0019 0.9999 -0.0026 0.1918 0.0593 -0.0292
-0.0019 -0.9999 0.0026 -0.1918 -0.0593 0.0292
1.0004 -0.0000 -0.0005 0.0053 0.0126 0.0607
-1.0004 0.0000 0.0005 -0.0053 -0.0126 -0.0607
13.7431 -2.5807 -0.1190 -0.4185 0.0101 0.9082
