#------------------------------------------------------------------------------
#$Date: 2023-01-19 10:35:37 +0200 (Thu, 19 Jan 2023) $
#$Revision: 280433 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106492.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_8106492
loop_
_publ_author_name
'Tzvetkov, Nikolay T.'
'Neumann, Beate'
'Stammler, Hans-Georg'
_publ_section_title
;
 The twinned crystal structure of
 (4SR)-7-benzyl-2,4,8,8-tetramethyl-7,8-dihydroimidazo[5,1-c][1,2,4]triazine-3,6(2H,4H)-dione,
 C16H20N4O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              231
_journal_page_last               233
_journal_paper_doi               10.1515/ncrs-2016-0218
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C16 H20 N4 O2'
_chemical_formula_sum            'C16 H20 N4 O2'
_chemical_formula_weight         300.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                100.534(4)
_cell_angle_beta                 94.120(4)
_cell_angle_gamma                94.752(4)
_cell_formula_units_Z            4
_cell_length_a                   9.0959(5)
_cell_length_b                   9.1993(5)
_cell_length_c                   18.5825(9)
_cell_measurement_reflns_used    8978
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      75.3320
_cell_measurement_theta_min      4.8760
_cell_volume                     1517.43(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'ORTEP-3 v1.0.3 [9]'
_computing_publication_material  'Olex2 1.2-ac2 [2]'
_computing_structure_refinement  'SHELXL-2014 [4]'
_computing_structure_solution    'SHELXT-2014 [3]'
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -120.00 -47.00   1.00    4.00    --  -38.50-178.00 150.00   73
  2  ω     13.00  55.00   1.00    4.00    --   43.45  77.00-180.00   42
  3  ω     67.00 112.00   1.00    4.00    --   43.45  77.00 120.00   45
  4  ω     13.00  73.00   1.00    4.00    --   43.45  77.00 -90.00   60
  5  ω    -27.00   5.00   1.00    4.00    --   43.45 -77.00 120.00   32
  6  ω     20.00  46.00   1.00    4.00    --   43.45  77.00 120.00   26
  7  ω     23.00  72.00   1.00    4.00    --   43.45  38.00-180.00   49
  8  ω     88.00 114.00   1.00    4.00    --   43.45  38.00-180.00   26
  9  ω     18.00  61.00   1.00    4.00    --   43.45  57.00-120.00   43
 10  ω     20.00  71.00   1.00    4.00    --   43.45 -77.00 120.00   51
 11  ω     87.00 113.00   1.00    4.00    --   43.45  77.00-180.00   26
 12  ω     57.00 121.00   1.00    4.00    --   43.45 178.00  90.00   64
 13  ω     69.00 101.00   1.00    4.00    --   43.45  77.00  60.00   32
 14  ω     25.00  66.00   1.00    4.00    --   43.45  38.00 -30.00   41
 15  ω     77.00 114.00   1.00    4.00    --   43.45  38.00 -30.00   37
 16  ω     14.00  67.00   1.00    4.00    --   43.45  77.00  60.00   53
 17  ω     74.00 111.00   1.00    4.00    --   43.45  77.00   0.00   37
 18  ω     13.00  68.00   1.00    4.00    --   43.45  77.00   0.00   55
 19  ω     65.00 104.00   1.00    4.00    --   43.45  57.00-120.00   39
 20  ω     68.00  94.00   1.00    4.00    --   43.45 178.00-180.00   26
 21  ω     83.00 120.00   1.00   16.00    --  108.74  61.00  30.00   37
 22  ω     83.00 109.00   1.00   16.00    --  108.74  61.00 150.00   26
 23  ω    128.00 154.00   1.00   16.00    --  108.74  75.00  99.81   26
 24  ω     87.00 117.00   1.00   16.00    --  108.74  51.00 -68.00   30
 25  ω     84.00 116.00   1.00   16.00    --  108.74  61.00 -90.00   32
 26  ω     80.00 174.00   1.00   16.00    --  108.74  77.00 -30.00   94
 27  ω     87.00 134.00   1.00   16.00    --  108.74  45.00 120.00   47
 28  ω    143.00 169.00   1.00   16.00    --  108.74  61.00 150.00   26
 29  ω     83.00 113.00   1.00   16.00    --  108.74  61.00  90.00   30
 30  ω     79.00 164.00   1.00   16.00    --  108.74  77.00-180.00   85
 31  ω     79.00 105.00   1.00   16.00    --  108.74  75.00  99.81   26
 32  ω     79.00 113.00   1.00   16.00    --  108.74  76.00 -44.41   34
 33  ω     54.00 135.00   1.00   16.00    --  108.74 -61.00 -90.00   81
 34  ω    119.00 145.00   1.00   16.00    --  108.74  77.00  30.00   26
 35  ω     79.00 105.00   1.00   16.00    --  108.74  77.00  30.00   26
 36  ω     79.00 105.00   1.00   16.00    --  108.74  77.00 -60.00   26
 37  ω     59.00 121.00   1.00   16.00    --  108.74-125.00  90.00   62
 38  ω     80.00 106.00   1.00   16.00    --  108.74  72.00 -60.25   26
 39  ω     84.00 110.00   1.00   16.00    --  108.74  61.00-120.00   26
 40  ω     83.00 113.00   1.00   16.00    --  108.74  61.00 -60.00   30
 41  ω     79.00 105.00   1.00   16.00    --  108.74  77.00   0.00   26
 42  ω    125.00 172.00   1.00   16.00    --  108.74  77.00   0.00   47
 43  ω     85.00 113.00   1.00   16.00    --  108.74  61.00  60.00   28
 44  ω     85.00 111.00   1.00   16.00    --  108.74  61.00   0.00   26
 45  ω     79.00 105.00   1.00   16.00    --  108.74  77.00-120.00   26
 46  ω     33.00  87.00   1.00   16.00    --  108.74 -94.00 120.00   54
 47  ω     85.00 111.00   1.00   16.00    --  108.74  61.00-150.00   26
 48  ω     79.00 158.00   1.00   16.00    --  108.74  77.00 120.00   79
 49  ω     30.00 102.00   1.00   16.00    --  108.74 -94.00-180.00   72
 50  ω     29.00 107.00   1.00   16.00    --  108.74 -94.00 -90.00   78
 51  ω     83.00 125.00   1.00   16.00    --  108.74  61.00-180.00   42
 52  ω    120.00 177.00   1.00   16.00    --  108.74  61.00 -90.00   57
 53  ω     81.00 175.00   1.00   16.00    --  108.74  77.00-150.00   94
 54  ω    116.00 146.00   1.00   16.00    --  108.74  76.00 -44.41   30
 55  ω     85.00 111.00   1.00   16.00    --  108.74  49.00-179.43   26
 56  ω     80.00 178.00   1.00   16.00    --  108.74  71.00  62.90   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       'CrysAlisPro convention [8]'
_diffrn_orient_matrix_UB_11      -0.1114476000
_diffrn_orient_matrix_UB_12      -0.0812579000
_diffrn_orient_matrix_UB_13      0.0413533000
_diffrn_orient_matrix_UB_21      0.1261937000
_diffrn_orient_matrix_UB_22      -0.0774819000
_diffrn_orient_matrix_UB_23      0.0320699000
_diffrn_orient_matrix_UB_31      0.0277107000
_diffrn_orient_matrix_UB_32      0.1291841000
_diffrn_orient_matrix_UB_33      0.0665479000
_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  0.0356
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14735
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_min         4.860
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.519
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
 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    1.315
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_recrystallization_method
;
 multiple non-merohedrically twinned. 
 4 domains were located and integrated. 
 Only reflections of the main domain were used for refinement.
;
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         5985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0801
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1486P)²+2.0195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2299
_refine_ls_wR_factor_ref         0.2371
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5460
_reflns_number_total             5985
_reflns_threshold_expression     'I > 2σ(I)'
_twin_special_details
;
Component 2 rotated by 178.7390° 
 around [-0.68 0.72 -0.15] (reciprocal) or [-0.69 0.72 0.00] (direct)
Component 3 rotated by 177.4826° 
 around [-0.01 -0.00 1.00] (reciprocal) or [0.14 0.34 0.93] (direct)
Component 4 rotated by 39.9610° 
 around [0.95 -0.04 -0.31] (reciprocal) or [1.00 0.03 -0.04] (direct)
;
_cod_data_source_file            suppl_ncrs-2016-0218_suppl.cif
_cod_data_source_block           NTZ-1307
_cod_original_cell_volume        1517.44(13)
_cod_database_code               8106492
_oxdiff_twin_integration_method  simultaneous
_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.
;
_shelxl_version_number           2014-3
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0439(4) 0.5744(5) 0.3932(2) 0.0470(10) Uani 1 1 d . . . . .
O2 O 0.2324(5) 0.1203(4) 0.2791(2) 0.0458(9) Uani 1 1 d . . . . .
N1 N 0.3521(5) 0.6063(5) 0.3969(2) 0.0346(9) Uani 1 1 d . . . . .
N2 N 0.2044(5) 0.6379(5) 0.4034(2) 0.0377(10) Uani 1 1 d . . . . .
N3 N 0.2537(5) 0.3670(5) 0.3370(2) 0.0355(9) Uani 1 1 d . . . . .
N4 N 0.4569(5) 0.2634(5) 0.3067(2) 0.0371(10) Uani 1 1 d . . . . .
C8 C 0.5962(6) 0.5028(7) 0.2952(3) 0.0416(12) Uani 1 1 d . . . . .
H8A H 0.6948 0.4688 0.2896 0.062 Uiso 1 1 calc R U . . .
H8B H 0.6062 0.6088 0.3172 0.062 Uiso 1 1 calc R U . . .
H8C H 0.5404 0.4873 0.2468 0.062 Uiso 1 1 calc R U . . .
C1 C 0.0838(6) 0.5383(6) 0.3863(3) 0.0363(11) Uani 1 1 d . . . . .
C2 C 0.1084(6) 0.3766(6) 0.3635(3) 0.0377(11) Uani 1 1 d . . . . .
H2 H 0.0318 0.3289 0.3229 0.045 Uiso 1 1 calc R U . . .
C3 C 0.3645(6) 0.4746(6) 0.3626(3) 0.0333(11) Uani 1 1 d . . . . .
C4 C 0.1929(7) 0.7934(7) 0.4341(3) 0.0437(13) Uani 1 1 d . . . . .
H4A H 0.2646 0.8256 0.4771 0.066 Uiso 1 1 calc R U . . .
H4B H 0.0925 0.8056 0.4487 0.066 Uiso 1 1 calc R U . . .
H4C H 0.2137 0.8539 0.3970 0.066 Uiso 1 1 calc R U . . .
C5 C 0.0916(8) 0.3000(8) 0.4291(3) 0.0511(14) Uani 1 1 d . . . . .
H5A H 0.1141 0.1966 0.4158 0.077 Uiso 1 1 calc R U . . .
H5B H -0.0102 0.3022 0.4429 0.077 Uiso 1 1 calc R U . . .
H5C H 0.1603 0.3519 0.4706 0.077 Uiso 1 1 calc R U . . .
C6 C 0.3081(6) 0.2344(7) 0.3042(3) 0.0375(11) Uani 1 1 d . . . . .
C7 C 0.5142(5) 0.4152(6) 0.3447(3) 0.0334(10) Uani 1 1 d . . . . .
C9 C 0.6078(6) 0.4130(7) 0.4161(3) 0.0420(12) Uani 1 1 d . . . . .
H9A H 0.5502 0.3583 0.4469 0.063 Uiso 1 1 calc R U . . .
H9B H 0.6357 0.5151 0.4424 0.063 Uiso 1 1 calc R U . . .
H9C H 0.6973 0.3642 0.4047 0.063 Uiso 1 1 calc R U . . .
C10 C 0.5509(6) 0.1548(6) 0.2730(3) 0.0377(11) Uani 1 1 d . . . . .
H10A H 0.6288 0.2066 0.2497 0.045 Uiso 1 1 calc R U . . .
H10B H 0.4903 0.0831 0.2336 0.045 Uiso 1 1 calc R U . . .
C11 C 0.6249(6) 0.0691(6) 0.3257(3) 0.0359(11) Uani 1 1 d . . . . .
C12 C 0.7742(7) 0.0571(7) 0.3275(3) 0.0466(14) Uani 1 1 d . . . . .
H12 H 0.8329 0.1090 0.2983 0.056 Uiso 1 1 calc R U . . .
C13 C 0.8399(7) -0.0294(8) 0.3711(4) 0.0515(15) Uani 1 1 d . . . . .
H13 H 0.9435 -0.0371 0.3716 0.062 Uiso 1 1 calc R U . . .
C14 C 0.7551(8) -0.1062(7) 0.4146(4) 0.0517(15) Uani 1 1 d . . . . .
H14 H 0.7997 -0.1677 0.4440 0.062 Uiso 1 1 calc R U . . .
C15 C 0.6081(8) -0.0911(7) 0.4140(4) 0.0537(16) Uani 1 1 d . . . . .
H15 H 0.5503 -0.1405 0.4445 0.064 Uiso 1 1 calc R U . . .
C16 C 0.5401(7) -0.0060(7) 0.3702(3) 0.0454(13) Uani 1 1 d . . . . .
H16 H 0.4366 0.0018 0.3701 0.055 Uiso 1 1 calc R U . . .
O3 O 0.3552(5) 0.0679(4) 0.0878(2) 0.0444(9) Uani 1 1 d . . . . .
O4 O -0.0546(4) 0.3845(4) 0.1996(2) 0.0398(8) Uani 1 1 d . . . . .
N5 N 0.4000(5) 0.4639(5) 0.1094(2) 0.0357(9) Uani 1 1 d . . . . .
N6 N 0.4240(5) 0.3119(5) 0.0963(2) 0.0340(9) Uani 1 1 d . . . . .
N7 N 0.1775(5) 0.3856(5) 0.1545(2) 0.0342(9) Uani 1 1 d . . . . .
N8 N 0.0875(5) 0.6009(5) 0.1917(2) 0.0352(9) Uani 1 1 d . . . . .
C17 C 0.3270(6) 0.1978(6) 0.0994(3) 0.0346(11) Uani 1 1 d . . . . .
C18 C 0.1681(6) 0.2328(6) 0.1148(3) 0.0354(11) Uani 1 1 d . . . . .
H18 H 0.1263 0.1646 0.1459 0.043 Uiso 1 1 calc R U . . .
C19 C 0.2801(6) 0.4909(6) 0.1394(3) 0.0326(10) Uani 1 1 d . . . . .
C20 C 0.5752(6) 0.2896(6) 0.0753(3) 0.0398(12) Uani 1 1 d . . . . .
H20A H 0.6074 0.3650 0.0471 0.060 Uiso 1 1 calc R U . . .
H20B H 0.5754 0.1905 0.0450 0.060 Uiso 1 1 calc R U . . .
H20C H 0.6430 0.2986 0.1196 0.060 Uiso 1 1 calc R U . . .
C21 C 0.0729(7) 0.2111(7) 0.0429(3) 0.0442(13) Uani 1 1 d . . . . .
H21A H -0.0295 0.2270 0.0527 0.066 Uiso 1 1 calc R U . . .
H21B H 0.0764 0.1098 0.0157 0.066 Uiso 1 1 calc R U . . .
H21C H 0.1101 0.2825 0.0136 0.066 Uiso 1 1 calc R U . . .
C22 C 0.0558(6) 0.4536(6) 0.1843(3) 0.0348(11) Uani 1 1 d . . . . .
C23 C 0.2274(6) 0.6433(6) 0.1624(3) 0.0354(11) Uani 1 1 d . . . . .
C24 C 0.2029(7) 0.7137(7) 0.0945(3) 0.0420(12) Uani 1 1 d . . . . .
H24A H 0.1367 0.6454 0.0570 0.063 Uiso 1 1 calc R U . . .
H24B H 0.2981 0.7338 0.0749 0.063 Uiso 1 1 calc R U . . .
H24C H 0.1580 0.8070 0.1082 0.063 Uiso 1 1 calc R U . . .
C25 C 0.3360(6) 0.7431(6) 0.2198(3) 0.0387(11) Uani 1 1 d . . . . .
H25A H 0.2986 0.8404 0.2332 0.058 Uiso 1 1 calc R U . . .
H25B H 0.4322 0.7553 0.1999 0.058 Uiso 1 1 calc R U . . .
H25C H 0.3475 0.6981 0.2635 0.058 Uiso 1 1 calc R U . . .
C26 C -0.0042(6) 0.7066(6) 0.2300(3) 0.0372(11) Uani 1 1 d . . . . .
H26A H 0.0614 0.7887 0.2613 0.045 Uiso 1 1 calc R U . . .
H26B H -0.0628 0.6564 0.2629 0.045 Uiso 1 1 calc R U . . .
C27 C -0.1090(6) 0.7721(6) 0.1810(3) 0.0342(10) Uani 1 1 d . . . . .
C28 C -0.0883(6) 0.9213(6) 0.1759(3) 0.0386(11) Uani 1 1 d . . . . .
H28 H -0.0028 0.9814 0.2003 0.046 Uiso 1 1 calc R U . . .
C29 C -0.1924(6) 0.9826(6) 0.1351(3) 0.0388(11) Uani 1 1 d . . . . .
H29 H -0.1791 1.0850 0.1327 0.047 Uiso 1 1 calc R U . . .
C30 C -0.3153(6) 0.8952(6) 0.0979(3) 0.0406(12) Uani 1 1 d . . . . .
H30 H -0.3866 0.9370 0.0700 0.049 Uiso 1 1 calc R U . . .
C31 C -0.3332(6) 0.7445(7) 0.1018(3) 0.0425(12) Uani 1 1 d . . . . .
H31 H -0.4163 0.6832 0.0756 0.051 Uiso 1 1 calc R U . . .
C32 C -0.2319(6) 0.6841(6) 0.1431(3) 0.0376(11) Uani 1 1 d . . . . .
H32 H -0.2459 0.5818 0.1458 0.045 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C3 N1 N2 113.6(4) . .
N1 N2 C4 112.4(5) . .
C1 N2 N1 125.7(4) . .
C1 N2 C4 121.8(5) . .
C3 N3 C2 120.7(4) . .
C3 N3 C6 111.5(4) . .
C6 N3 C2 124.6(5) . .
C6 N4 C7 114.4(4) . .
C6 N4 C10 122.3(5) . .
C10 N4 C7 123.3(4) . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
O1 C1 N2 122.2(5) . .
O1 C1 C2 119.8(5) . .
N2 C1 C2 117.8(5) . .
N3 C2 C1 108.9(4) . .
N3 C2 H2 109.0 . .
N3 C2 C5 112.0(5) . .
C1 C2 H2 109.0 . .
C1 C2 C5 108.9(5) . .
C5 C2 H2 109.0 . .
N1 C3 N3 126.8(5) . .
N1 C3 C7 123.7(5) . .
N3 C3 C7 109.5(4) . .
N2 C4 H4A 109.5 . .
N2 C4 H4B 109.5 . .
N2 C4 H4C 109.5 . .
H4A C4 H4B 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
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 124.7(5) . .
O2 C6 N4 128.9(5) . .
N4 C6 N3 106.5(5) . .
N4 C7 C8 112.7(4) . .
N4 C7 C3 98.1(4) . .
N4 C7 C9 111.4(4) . .
C8 C7 C3 112.2(4) . .
C8 C7 C9 112.0(4) . .
C9 C7 C3 109.6(4) . .
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 108.6 . .
N4 C10 H10B 108.6 . .
N4 C10 C11 114.6(4) . .
H10A C10 H10B 107.6 . .
C11 C10 H10A 108.6 . .
C11 C10 H10B 108.6 . .
C12 C11 C10 120.5(5) . .
C12 C11 C16 118.9(5) . .
C16 C11 C10 120.5(5) . .
C11 C12 H12 119.6 . .
C11 C12 C13 120.7(6) . .
C13 C12 H12 119.6 . .
C12 C13 H13 119.8 . .
C12 C13 C14 120.4(6) . .
C14 C13 H13 119.8 . .
C13 C14 H14 120.7 . .
C15 C14 C13 118.7(6) . .
C15 C14 H14 120.7 . .
C14 C15 H15 119.1 . .
C14 C15 C16 121.7(6) . .
C16 C15 H15 119.1 . .
C11 C16 H16 120.2 . .
C15 C16 C11 119.5(6) . .
C15 C16 H16 120.2 . .
C19 N5 N6 113.6(4) . .
N5 N6 C20 111.5(4) . .
C17 N6 N5 127.1(4) . .
C17 N6 C20 121.4(4) . .
C19 N7 C18 120.5(4) . .
C19 N7 C22 110.1(4) . .
C22 N7 C18 123.9(4) . .
C22 N8 C23 113.7(4) . .
C22 N8 C26 122.2(4) . .
C26 N8 C23 124.0(4) . .
O3 C17 N6 123.9(5) . .
O3 C17 C18 119.1(5) . .
N6 C17 C18 116.9(4) . .
N7 C18 C17 107.2(4) . .
N7 C18 H18 109.5 . .
N7 C18 C21 111.8(4) . .
C17 C18 H18 109.5 . .
C21 C18 C17 109.4(4) . .
C21 C18 H18 109.5 . .
N5 C19 N7 125.1(5) . .
N5 C19 C23 125.7(5) . .
N7 C19 C23 109.1(4) . .
N6 C20 H20A 109.5 . .
N6 C20 H20B 109.5 . .
N6 C20 H20C 109.5 . .
H20A C20 H20B 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C18 C21 H21A 109.5 . .
C18 C21 H21B 109.5 . .
C18 C21 H21C 109.5 . .
H21A C21 H21B 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
O4 C22 N7 123.7(5) . .
O4 C22 N8 129.1(5) . .
N8 C22 N7 107.2(4) . .
N8 C23 C19 99.7(4) . .
N8 C23 C24 112.3(4) . .
N8 C23 C25 112.7(4) . .
C19 C23 C24 109.3(4) . .
C19 C23 C25 111.8(4) . .
C25 C23 C24 110.6(5) . .
C23 C24 H24A 109.5 . .
C23 C24 H24B 109.5 . .
C23 C24 H24C 109.5 . .
H24A C24 H24B 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C23 C25 H25A 109.5 . .
C23 C25 H25B 109.5 . .
C23 C25 H25C 109.5 . .
H25A C25 H25B 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
N8 C26 H26A 108.5 . .
N8 C26 H26B 108.5 . .
N8 C26 C27 115.1(4) . .
H26A C26 H26B 107.5 . .
C27 C26 H26A 108.5 . .
C27 C26 H26B 108.5 . .
C28 C27 C26 120.9(5) . .
C32 C27 C26 119.5(5) . .
C32 C27 C28 119.5(5) . .
C27 C28 H28 120.0 . .
C29 C28 C27 120.1(5) . .
C29 C28 H28 120.0 . .
C28 C29 H29 119.8 . .
C30 C29 C28 120.4(5) . .
C30 C29 H29 119.8 . .
C29 C30 H30 120.5 . .
C29 C30 C31 119.1(5) . .
C31 C30 H30 120.5 . .
C30 C31 H31 119.6 . .
C32 C31 C30 120.7(5) . .
C32 C31 H31 119.6 . .
C27 C32 H32 119.9 . .
C31 C32 C27 120.2(5) . .
C31 C32 H32 119.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.244(7) .
O2 C6 1.203(7) .
N1 N2 1.408(6) .
N1 C3 1.280(7) .
N2 C1 1.349(7) .
N2 C4 1.455(7) .
N3 C2 1.447(7) .
N3 C3 1.348(7) .
N3 C6 1.406(7) .
N4 C6 1.354(7) .
N4 C7 1.479(7) .
N4 C10 1.453(7) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C8 C7 1.524(8) .
C1 C2 1.510(8) .
C2 H2 1.0000 .
C2 C5 1.525(8) .
C3 C7 1.544(7) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C7 C9 1.528(7) .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C10 C11 1.520(8) .
C11 C12 1.370(8) .
C11 C16 1.402(9) .
C12 H12 0.9500 .
C12 C13 1.375(9) .
C13 H13 0.9500 .
C13 C14 1.399(10) .
C14 H14 0.9500 .
C14 C15 1.356(10) .
C15 H15 0.9500 .
C15 C16 1.378(9) .
C16 H16 0.9500 .
O3 C17 1.227(7) .
O4 C22 1.223(7) .
N5 N6 1.413(6) .
N5 C19 1.282(7) .
N6 C17 1.326(7) .
N6 C20 1.477(7) .
N7 C18 1.456(7) .
N7 C19 1.369(7) .
N7 C22 1.415(7) .
N8 C22 1.341(7) .
N8 C23 1.471(7) .
N8 C26 1.454(7) .
C17 C18 1.542(7) .
C18 H18 1.0000 .
C18 C21 1.510(8) .
C19 C23 1.516(7) .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C23 C24 1.531(7) .
C23 C25 1.516(8) .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C26 H26A 0.9900 .
C26 H26B 0.9900 .
C26 C27 1.507(7) .
C27 C28 1.392(8) .
C27 C32 1.389(8) .
C28 H28 0.9500 .
C28 C29 1.390(8) .
C29 H29 0.9500 .
C29 C30 1.382(8) .
C30 H30 0.9500 .
C30 C31 1.399(8) .
C31 H31 0.9500 .
C31 C32 1.373(8) .
C32 H32 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
O1 C1 C2 N3 161.9(5) . . . .
O1 C1 C2 C5 -75.7(6) . . . .
N1 N2 C1 O1 -179.6(5) . . . .
N1 N2 C1 C2 4.9(7) . . . .
N1 C3 C7 N4 179.8(5) . . . .
N1 C3 C7 C8 -61.5(7) . . . .
N1 C3 C7 C9 63.6(7) . . . .
N2 N1 C3 N3 -3.6(7) . . . .
N2 N1 C3 C7 176.8(4) . . . .
N2 C1 C2 N3 -22.5(6) . . . .
N2 C1 C2 C5 99.9(6) . . . .
N3 C3 C7 N4 0.1(5) . . . .
N3 C3 C7 C8 118.8(5) . . . .
N3 C3 C7 C9 -116.2(5) . . . .
N4 C10 C11 C12 -130.0(5) . . . .
N4 C10 C11 C16 53.7(7) . . . .
C2 N3 C3 N1 -17.3(8) . . . .
C2 N3 C3 C7 162.4(4) . . . .
C2 N3 C6 O2 17.8(8) . . . .
C2 N3 C6 N4 -162.7(5) . . . .
C3 N1 N2 C1 9.5(7) . . . .
C3 N1 N2 C4 -172.6(5) . . . .
C3 N3 C2 C1 28.8(6) . . . .
C3 N3 C2 C5 -91.7(6) . . . .
C3 N3 C6 O2 177.7(5) . . . .
C3 N3 C6 N4 -2.8(6) . . . .
C4 N2 C1 O1 2.7(8) . . . .
C4 N2 C1 C2 -172.8(5) . . . .
C6 N3 C2 C1 -173.1(4) . . . .
C6 N3 C2 C5 66.4(7) . . . .
C6 N3 C3 N1 -178.0(5) . . . .
C6 N3 C3 C7 1.7(6) . . . .
C6 N4 C7 C8 -120.2(5) . . . .
C6 N4 C7 C3 -1.9(5) . . . .
C6 N4 C7 C9 112.9(5) . . . .
C6 N4 C10 C11 -98.1(6) . . . .
C7 N4 C6 O2 -177.6(5) . . . .
C7 N4 C6 N3 3.0(6) . . . .
C7 N4 C10 C11 83.5(6) . . . .
C10 N4 C6 O2 3.9(9) . . . .
C10 N4 C6 N3 -175.6(4) . . . .
C10 N4 C7 C8 58.3(6) . . . .
C10 N4 C7 C3 176.6(4) . . . .
C10 N4 C7 C9 -68.6(6) . . . .
C10 C11 C12 C13 -175.1(6) . . . .
C10 C11 C16 C15 175.7(6) . . . .
C11 C12 C13 C14 -0.3(9) . . . .
C12 C11 C16 C15 -0.7(9) . . . .
C12 C13 C14 C15 -1.3(10) . . . .
C13 C14 C15 C16 1.9(10) . . . .
C14 C15 C16 C11 -0.9(10) . . . .
C16 C11 C12 C13 1.2(9) . . . .
O3 C17 C18 N7 157.4(5) . . . .
O3 C17 C18 C21 -81.2(6) . . . .
N5 N6 C17 O3 -179.5(5) . . . .
N5 N6 C17 C18 3.5(8) . . . .
N5 C19 C23 N8 179.6(5) . . . .
N5 C19 C23 C24 61.7(7) . . . .
N5 C19 C23 C25 -61.0(7) . . . .
N6 N5 C19 N7 -3.6(7) . . . .
N6 N5 C19 C23 177.8(5) . . . .
N6 C17 C18 N7 -25.5(6) . . . .
N6 C17 C18 C21 95.9(6) . . . .
N7 C19 C23 N8 0.8(5) . . . .
N7 C19 C23 C24 -117.1(5) . . . .
N7 C19 C23 C25 120.2(5) . . . .
N8 C26 C27 C28 -111.3(6) . . . .
N8 C26 C27 C32 71.7(6) . . . .
C18 N7 C19 N5 -22.4(8) . . . .
C18 N7 C19 C23 156.4(4) . . . .
C18 N7 C22 O4 22.9(8) . . . .
C18 N7 C22 N8 -157.5(4) . . . .
C19 N5 N6 C17 12.9(7) . . . .
C19 N5 N6 C20 -169.1(4) . . . .
C19 N7 C18 C17 34.9(6) . . . .
C19 N7 C18 C21 -84.9(6) . . . .
C19 N7 C22 O4 176.6(5) . . . .
C19 N7 C22 N8 -3.7(6) . . . .
C20 N6 C17 O3 2.7(8) . . . .
C20 N6 C17 C18 -174.3(5) . . . .
C22 N7 C18 C17 -173.9(4) . . . .
C22 N7 C18 C21 66.2(6) . . . .
C22 N7 C19 N5 -177.2(5) . . . .
C22 N7 C19 C23 1.7(6) . . . .
C22 N8 C23 C19 -3.3(6) . . . .
C22 N8 C23 C24 112.3(5) . . . .
C22 N8 C23 C25 -121.9(5) . . . .
C22 N8 C26 C27 -100.8(6) . . . .
C23 N8 C22 O4 -175.9(5) . . . .
C23 N8 C22 N7 4.4(6) . . . .
C23 N8 C26 C27 83.7(6) . . . .
C26 N8 C22 O4 8.1(8) . . . .
C26 N8 C22 N7 -171.5(4) . . . .
C26 N8 C23 C19 172.6(4) . . . .
C26 N8 C23 C24 -71.8(6) . . . .
C26 N8 C23 C25 53.9(6) . . . .
C26 C27 C28 C29 -174.9(5) . . . .
C26 C27 C32 C31 176.1(5) . . . .
C27 C28 C29 C30 -1.6(8) . . . .
C28 C27 C32 C31 -1.0(8) . . . .
C28 C29 C30 C31 -0.1(8) . . . .
C29 C30 C31 C32 1.2(8) . . . .
C30 C31 C32 C27 -0.7(8) . . . .
C32 C27 C28 C29 2.1(7) . . . .
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.5158 3214 13177 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.2399 0 12647 nmt -0.0426 -0.9917 0.0048 -1.0023 0.0489 0.0108 0.1715 -0.2478
-1.0049
3 0.1875 0 11563 nmt -0.9962 -0.0477 -0.0067 0.0430 -1.0051 -0.0114 0.2736
0.7418 1.0056
4 0.0568 0 8737 nmt 1.0021 0.0619 0.0028 -0.1197 0.6380 -0.3236 0.0139 1.3066
0.8927
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{d53cc1d4-8f78-4445-a737-dd6391767f2a} '_publcif_info_datablock.publ_exptl'
loop_
_publcif_info_cif.paper_type
CE
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{d53cc1d4-8f78-4445-a737-dd6391767f2a} ? ? ?
{02146d7e-a8a5-48c2-a384-b9e9e5f8c306} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
