#------------------------------------------------------------------------------
#$Date: 2023-06-16 10:36:55 +0300 (Fri, 16 Jun 2023) $
#$Revision: 284487 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/73/8107381.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_8107381
loop_
_publ_author_name
'Al-Wahaibi, Lamya H.'
'Blacque, Olivier'
'Al-Shaalan, Nora H.'
'Tiekink, Edward R. T.'
'El-Emam, Ali A.'
_publ_section_title
;
 Crystal structure of
 2-({[5-(adamantan-2-yl)-2-sulfanylidene-1,3,4-oxadiazolidin-3-yl]methyl}amino)benzonitrile,
 C20H22N4OS
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              159
_journal_page_last               161
_journal_paper_doi               10.1515/ncrs-2022-0511
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C20 H22 N4 O S'
_chemical_formula_sum            'C20 H22 N4 O S'
_chemical_formula_weight         366.47
_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   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                114.083(5)
_cell_angle_beta                 104.326(4)
_cell_angle_gamma                90.369(3)
_cell_formula_units_Z            2
_cell_length_a                   6.8528(3)
_cell_length_b                   11.3498(5)
_cell_length_c                   13.3896(9)
_cell_measurement_reflns_used    5077
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      78.4
_cell_measurement_theta_min      15.7
_cell_volume                     914.38(9)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'OLEX2 [4]'
_computing_publication_material  'OLEX2 [4]'
_computing_structure_refinement  'SHELXL [3]'
_computing_structure_solution    'SHELXT [2]'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -26.00  28.00   0.50    0.70    --  -51.56  19.00-120.00  108
  2  ω    -35.00 -10.00   0.50    0.70    --  -86.25  30.00  30.00   50
  3  ω    -73.00  21.00   0.50    0.70    --  -51.56  77.00  30.00  188
  4  ω     30.00 124.00   0.50    0.70    --   51.56  77.00  60.00  188
  5  ω    105.00 178.00   0.50    0.70    --  107.75  45.00 150.00  146
  6  ω     99.00 134.00   0.50    0.70    --  107.75  15.00  90.00   70
  7  ω     99.00 159.00   0.50    0.70    --  107.75  30.00  90.00  120
  8  ω    103.00 141.00   0.50    0.70    --  107.75  30.00 -30.00   76
  9  ω     98.00 150.00   0.50    0.70    --  107.75  15.00 -30.00  104
 10  ω     97.00 129.00   0.50    0.70    --  107.75  45.00-120.00   64
 11  ω    147.00 174.00   0.50    0.70    --  107.75  45.00-120.00   54
 12  ω    144.00 178.00   0.50    0.70    --  107.75  30.00-180.00   68
 13  ω    117.00 171.00   0.50    0.70    --  107.75  15.00-150.00  108
 14  ω     99.00 138.00   0.50    0.70    --  107.75  30.00-180.00   78
 15  ω     99.00 137.00   0.50    0.70    --  107.75 111.00-120.00   76
 16  ω     38.00  64.00   0.50    0.70    --  107.75 -61.00  60.00   52
 17  ω     36.00  95.00   0.50    0.70    --  107.75 -94.00   0.00  118
 18  ω     66.00 112.00   0.50    0.70    --  107.75-111.00 -60.00   92
 19  ω     96.00 129.00   0.50    0.70    --  107.75-140.00 -54.44   66
 20  ω     96.00 133.00   0.50    0.70    --  107.75-146.00  28.53   74
 21  ω     79.00 112.00   0.50    0.70    --  107.75-111.00 150.00   66
 22  ω     48.00  73.00   0.50    0.70    --  107.75-146.00  28.53   50
 23  ω     51.00 111.00   0.50    0.70    --  107.75-111.00   0.00  120
 24  ω     85.00 123.00   0.50    0.70    --  107.75-133.00 -89.68   76
 25  ω     59.00 112.00   0.50    0.70    --  107.75-111.00-120.00  106
 26  ω     52.00  78.00   0.50    0.70    --  107.75-133.00 -89.68   52
 27  ω     44.00  91.00   0.50    0.70    --  107.75-140.00 -54.44   94
 28  ω     41.00 112.00   0.50    0.70    --  107.75-111.00  60.00  142
 29  ω     46.00  79.00   0.50    0.70    --  107.75 -94.00 -60.00   66
 30  ω     48.00  78.00   0.50    0.70    --  107.75 -77.00   0.00   60
 31  ω     35.00 101.00   0.50    0.70    --  107.75 -77.00  60.00  132
 32  ω     35.00 101.00   0.50    0.70    --  107.75 -94.00 150.00  132
 33  ω     38.00  72.00   0.50    0.70    --  107.75 -77.00  90.00   68
 34  ω     34.00 108.00   0.50    0.70    --  107.75 -94.00  60.00  148
 35  ω     39.00  68.00   0.50    0.70    --  107.75 -61.00  90.00   58
 36  ω     37.00  63.00   0.50    0.70    --  107.75 -61.00 150.00   52
 37  ω     35.00  97.00   0.50    0.70    --  107.75 -77.00 150.00  124
 38  ω     36.00  63.00   0.50    0.70    --  107.75-111.00 150.00   54
 39  ω     30.00  98.00   0.50    0.70    --   51.56-125.00   0.00  136
 40  ω     42.00  77.00   0.50    0.70    --  107.75 -94.00 -90.00   70
 41  ω     39.00  70.00   0.50    0.70    --  107.75 -61.00 -90.00   62
 42  ω     39.00  65.00   0.50    0.70    --  107.75 -61.00 -30.00   52
 43  ω     31.00  61.00   0.50    0.70    --  107.75-111.00 -60.00   60
 44  ω     41.00  71.00   0.50    0.70    --  107.75 -61.00-180.00   60
 45  ω     50.00  77.00   0.50    0.70    --  107.75 -77.00-180.00   54
 46  ω   -128.00 -42.00   0.50    0.70    --  -51.56 -38.00 150.00  172
 47  ω   -127.00 -82.00   0.50    0.70    --  -51.56 -99.00 -30.00   90
 48  ω   -124.00 -30.00   0.50    0.70    --  -51.56 -77.00 -90.00  188
 49  ω   -126.00 -70.00   0.50    0.70    --  -51.56-125.00 150.00  112
 50  ω   -164.00 -77.00   0.50    0.70    --  -86.25 -30.00  30.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2019886000
_diffrn_orient_matrix_UB_12      -0.0261885000
_diffrn_orient_matrix_UB_13      0.0644911000
_diffrn_orient_matrix_UB_21      0.0339863000
_diffrn_orient_matrix_UB_22      -0.0945853000
_diffrn_orient_matrix_UB_23      -0.1139314000
_diffrn_orient_matrix_UB_31      0.1126498000
_diffrn_orient_matrix_UB_32      0.1131303000
_diffrn_orient_matrix_UB_33      -0.0069377000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24423
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.553
_diffrn_reflns_theta_min         3.760
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.701
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro [1]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       plate
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.289
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         24423
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0844
_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)+(0.1623P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2079
_refine_ls_wR_factor_ref         0.2217
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                19275
_reflns_number_total             24423
_reflns_threshold_expression     'I > 2σ(I)'
_twin_special_details
;
Component 2 rotated by 179.9916° 
 around [0.00 -0.00 1.00] (reciprocal) or [0.40 0.40 0.82] (direct)
;
_cod_data_source_file            suppl_j_ncrs-2022-0511_suppl.cif
_cod_data_source_block           emam11_tw
_cod_database_code               8107381
_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   0.967
_shelx_estimated_absorpt_t_min   0.738
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N2-H2
 0.87 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C13(H13), C15(H15), C18(H18)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C12(H12A,H12B), C14(H14A,H14B), C16(H16A,H16B), C17(H17A,H17B),
 C19(H19A,H19B), C20(H20A,H20B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.311
_oxdiff_exptl_absorpt_empirical_full_min 0.832
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
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
C1 C 0.3603(6) 0.8333(3) 0.6742(3) 0.0283(8) Uani 1 1 d . . . . .
C2 C 0.5068(6) 0.7458(3) 0.6457(3) 0.0278(8) Uani 1 1 d . . . . .
C3 C 0.5088(7) 0.6359(4) 0.6694(4) 0.0350(10) Uani 1 1 d . . . . .
H3 H 0.410156 0.619318 0.702435 0.042 Uiso 1 1 calc R . . . .
C4 C 0.6509(8) 0.5528(4) 0.6455(4) 0.0372(10) Uani 1 1 d . . . . .
H4 H 0.652854 0.479596 0.662962 0.045 Uiso 1 1 calc R . . . .
C5 C 0.7932(7) 0.5761(3) 0.5951(4) 0.0340(9) Uani 1 1 d . . . . .
H5 H 0.892182 0.518273 0.578294 0.041 Uiso 1 1 calc R . . . .
C6 C 0.7923(6) 0.6827(3) 0.5691(3) 0.0292(8) Uani 1 1 d . . . . .
H6 H 0.888634 0.696007 0.533294 0.035 Uiso 1 1 calc R . . . .
C7 C 0.6515(6) 0.7703(3) 0.5950(3) 0.0248(8) Uani 1 1 d . . . . .
C8 C 0.7895(6) 0.9163(3) 0.5261(3) 0.0254(8) Uani 1 1 d . . . . .
H8A H 0.925414 0.896205 0.556915 0.031 Uiso 1 1 calc R . . . .
H8B H 0.798008 1.011363 0.549199 0.031 Uiso 1 1 calc R . . . .
C9 C 0.8366(6) 0.7691(3) 0.3337(3) 0.0233(8) Uani 1 1 d . . . . .
C10 C 0.5462(6) 0.7960(3) 0.2346(3) 0.0243(8) Uani 1 1 d . . . . .
C11 C 0.3895(6) 0.7742(3) 0.1280(3) 0.0235(7) Uani 1 1 d . . . . .
C12 C 0.3016(6) 0.6287(3) 0.0660(3) 0.0263(8) Uani 1 1 d . . . . .
H12A H 0.412221 0.574220 0.050279 0.032 Uiso 1 1 calc R . . . .
H12B H 0.237979 0.604900 0.115127 0.032 Uiso 1 1 calc R . . . .
C13 C 0.1439(6) 0.6038(3) -0.0454(3) 0.0293(8) Uani 1 1 d . . . . .
H13 H 0.088109 0.509684 -0.085046 0.035 Uiso 1 1 calc R . . . .
C14 C 0.2442(7) 0.6392(4) -0.1220(3) 0.0322(9) Uani 1 1 d . . . . .
H14A H 0.355671 0.585673 -0.138316 0.039 Uiso 1 1 calc R . . . .
H14B H 0.143235 0.621426 -0.195166 0.039 Uiso 1 1 calc R . . . .
C15 C 0.3283(7) 0.7839(4) -0.0614(4) 0.0307(9) Uani 1 1 d . . . . .
H15 H 0.392055 0.807313 -0.111492 0.037 Uiso 1 1 calc R . . . .
C16 C 0.4882(6) 0.8091(3) 0.0495(3) 0.0272(8) Uani 1 1 d . . . . .
H16A H 0.546063 0.901778 0.088068 0.033 Uiso 1 1 calc R . . . .
H16B H 0.599666 0.755638 0.033004 0.033 Uiso 1 1 calc R . . . .
C17 C 0.1557(7) 0.8665(4) -0.0363(4) 0.0339(9) Uani 1 1 d . . . . .
H17A H 0.052801 0.850609 -0.108288 0.041 Uiso 1 1 calc R . . . .
H17B H 0.209495 0.959864 0.001956 0.041 Uiso 1 1 calc R . . . .
C18 C 0.0579(6) 0.8306(4) 0.0408(4) 0.0310(9) Uani 1 1 d . . . . .
H18 H -0.054954 0.884468 0.057081 0.037 Uiso 1 1 calc R . . . .
C19 C 0.2158(6) 0.8569(3) 0.1524(3) 0.0267(8) Uani 1 1 d . . . . .
H19A H 0.152323 0.835019 0.202494 0.032 Uiso 1 1 calc R . . . .
H19B H 0.269868 0.950240 0.191907 0.032 Uiso 1 1 calc R . . . .
C20 C -0.0282(6) 0.6860(4) -0.0208(4) 0.0321(9) Uani 1 1 d . . . . .
H20A H -0.094507 0.662140 0.027267 0.038 Uiso 1 1 calc R . . . .
H20B H -0.131178 0.669578 -0.093000 0.038 Uiso 1 1 calc R . . . .
N1 N 0.2453(6) 0.9064(3) 0.6983(3) 0.0366(8) Uani 1 1 d . . . . .
N2 N 0.6479(5) 0.8798(3) 0.5738(3) 0.0275(7) Uani 1 1 d D . . . .
H2 H 0.566(6) 0.934(3) 0.598(4) 0.031(11) Uiso 1 1 d D . . . .
N3 N 0.7322(5) 0.8487(3) 0.4011(3) 0.0233(7) Uani 1 1 d . . . . .
N4 N 0.5488(5) 0.8661(3) 0.3387(3) 0.0242(7) Uani 1 1 d . . . . .
O1 O 0.7161(4) 0.7336(2) 0.2254(2) 0.0262(6) Uani 1 1 d . . . . .
S1 S 1.06010(15) 0.71962(8) 0.36407(9) 0.0295(3) Uani 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'
S S 0.3331 0.5567 '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
0 -1 0 0.0364
0 1 0 0.0444
0 0 1 0.0132
0 0 -1 0.0010
-1 -1 1 0.0685
1 1 -1 0.0600
-1 5 -1 0.0472
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
N1 C1 C2 178.5(4) . .
C3 C2 C1 119.8(3) . .
C3 C2 C7 120.1(4) . .
C7 C2 C1 120.1(3) . .
C2 C3 H3 119.6 . .
C4 C3 C2 120.7(3) . .
C4 C3 H3 119.6 . .
C3 C4 H4 120.3 . .
C3 C4 C5 119.4(3) . .
C5 C4 H4 120.3 . .
C4 C5 H5 119.5 . .
C6 C5 C4 120.9(4) . .
C6 C5 H5 119.5 . .
C5 C6 H6 119.7 . .
C5 C6 C7 120.6(3) . .
C7 C6 H6 119.7 . .
C6 C7 C2 118.2(3) . .
N2 C7 C2 119.0(3) . .
N2 C7 C6 122.8(3) . .
H8A C8 H8B 107.9 . .
N2 C8 H8A 109.1 . .
N2 C8 H8B 109.1 . .
N2 C8 N3 112.3(3) . .
N3 C8 H8A 109.1 . .
N3 C8 H8B 109.1 . .
N3 C9 O1 104.8(3) . .
N3 C9 S1 131.3(3) . .
O1 C9 S1 124.0(3) . .
N4 C10 C11 129.7(4) . .
N4 C10 O1 112.6(3) . .
O1 C10 C11 117.8(3) . .
C10 C11 C12 109.0(3) . .
C10 C11 C16 109.4(3) . .
C10 C11 C19 111.3(3) . .
C12 C11 C16 108.8(3) . .
C19 C11 C12 108.9(3) . .
C19 C11 C16 109.4(3) . .
C11 C12 H12A 109.7 . .
C11 C12 H12B 109.7 . .
H12A C12 H12B 108.2 . .
C13 C12 C11 109.7(3) . .
C13 C12 H12A 109.7 . .
C13 C12 H12B 109.7 . .
C12 C13 H13 109.3 . .
C12 C13 C14 109.5(3) . .
C14 C13 H13 109.3 . .
C20 C13 C12 109.7(3) . .
C20 C13 H13 109.3 . .
C20 C13 C14 109.7(3) . .
C13 C14 H14A 109.8 . .
C13 C14 H14B 109.8 . .
H14A C14 H14B 108.3 . .
C15 C14 C13 109.2(3) . .
C15 C14 H14A 109.8 . .
C15 C14 H14B 109.8 . .
C14 C15 H15 109.3 . .
C16 C15 C14 109.3(3) . .
C16 C15 H15 109.3 . .
C16 C15 C17 109.9(3) . .
C17 C15 C14 109.7(3) . .
C17 C15 H15 109.3 . .
C11 C16 H16A 109.8 . .
C11 C16 H16B 109.8 . .
C15 C16 C11 109.5(3) . .
C15 C16 H16A 109.8 . .
C15 C16 H16B 109.8 . .
H16A C16 H16B 108.2 . .
C15 C17 H17A 109.8 . .
C15 C17 H17B 109.8 . .
C15 C17 C18 109.3(3) . .
H17A C17 H17B 108.3 . .
C18 C17 H17A 109.8 . .
C18 C17 H17B 109.8 . .
C17 C18 H18 109.3 . .
C17 C18 C20 109.1(3) . .
C19 C18 C17 109.8(3) . .
C19 C18 H18 109.3 . .
C19 C18 C20 110.2(3) . .
C20 C18 H18 109.3 . .
C11 C19 H19A 109.8 . .
C11 C19 H19B 109.8 . .
C18 C19 C11 109.5(3) . .
C18 C19 H19A 109.8 . .
C18 C19 H19B 109.8 . .
H19A C19 H19B 108.2 . .
C13 C20 C18 109.3(3) . .
C13 C20 H20A 109.8 . .
C13 C20 H20B 109.8 . .
C18 C20 H20A 109.8 . .
C18 C20 H20B 109.8 . .
H20A C20 H20B 108.3 . .
C7 N2 C8 123.9(3) . .
C7 N2 H2 118(3) . .
C8 N2 H2 118(3) . .
C9 N3 C8 128.6(3) . .
C9 N3 N4 112.0(3) . .
N4 N3 C8 119.4(3) . .
C10 N4 N3 103.8(3) . .
C9 O1 C10 106.9(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.426(6) .
C1 N1 1.153(6) .
C2 C3 1.406(5) .
C2 C7 1.416(5) .
C3 H3 0.9500 .
C3 C4 1.363(7) .
C4 H4 0.9500 .
C4 C5 1.395(6) .
C5 H5 0.9500 .
C5 C6 1.388(5) .
C6 H6 0.9500 .
C6 C7 1.391(6) .
C7 N2 1.383(4) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C8 N2 1.428(5) .
C8 N3 1.472(5) .
C9 N3 1.343(5) .
C9 O1 1.368(5) .
C9 S1 1.648(4) .
C10 C11 1.484(5) .
C10 N4 1.288(5) .
C10 O1 1.373(5) .
C11 C12 1.550(5) .
C11 C16 1.552(4) .
C11 C19 1.536(5) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C12 C13 1.526(6) .
C13 H13 1.0000 .
C13 C14 1.539(5) .
C13 C20 1.525(6) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C14 C15 1.535(5) .
C15 H15 1.0000 .
C15 C16 1.527(6) .
C15 C17 1.531(6) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C17 C18 1.537(5) .
C18 H18 1.0000 .
C18 C19 1.525(6) .
C18 C20 1.537(5) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
N2 H2 0.85(2) .
N3 N4 1.390(4) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 N4 0.85(2) 2.30(3) 3.095(4) 156(4) 2_676 yes
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 0.5735 8782 6799 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.4265 8855 6799 nmt -1.0002 0.0003 0.0002 0.0000 -0.9998 -0.0006 0.9779
0.9660 1.0004
