#------------------------------------------------------------------------------
#$Date: 2025-04-05 07:10:43 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299129 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/03/7160364.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_7160364
loop_
_publ_author_name
'Toman, Daniel'
'Nemec, Ivan'
'Kurka, Ondřej'
'Přibylka, Adam'
'Cankař, Petr'
_publ_section_title
;
 Axially chiral dimethylaminobenzimidazoles and their preliminary
 evaluation as acyl-transfer reagents.
;
_journal_issue                   11
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2672
_journal_page_last               2682
_journal_paper_doi               10.1039/d4ob02052a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C23 H25 N4, Cl, H2 O'
_chemical_formula_sum            'C23 H27 Cl N4 O'
_chemical_formula_weight         410.93
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-02
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2024-12-02 deposited with the CCDC.	2025-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.13520(10)
_cell_length_b                   11.23990(10)
_cell_length_c                   18.2950(2)
_cell_measurement_reflns_used    8454
_cell_measurement_temperature    99.98(15)
_cell_measurement_theta_max      68.3090
_cell_measurement_theta_min      4.6030
_cell_volume                     2084.14(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(15)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  25.00   0.50    0.50    --  -42.75  70.00 -99.00   82
  2  ω    -45.00 -20.00   0.50    0.50    --  -42.75  70.00 -99.00   50
  3  ω    -45.00 -20.00   0.50    0.50    --  -42.75 -70.00 129.00   50
  4  ω    -21.00  15.00   0.50    0.50    --   44.32 -70.00 129.00   72
  5  ω     41.00  66.00   0.50    0.50    --   44.32 -70.00 129.00   50
  6  ω   -146.00 -93.00   0.50    3.50    --  -93.31 -70.00 129.00  106
  7  ω    -81.00 -56.00   0.50    3.50    --  -93.31  70.00 -99.00   50
  8  ω     29.00  64.00   0.50    3.50    --   94.87 -70.00 129.00   70
  9  ω      6.00  31.00   0.50    0.50    --  -42.75  11.00  60.00   50
 10  ω     65.00 104.00   0.50    0.50    --   44.32 138.00   0.00   78
 11  ω    -21.00  30.00   0.50    0.50    --   44.32 -32.00   0.00  102
 12  ω    -21.00  18.00   0.50    0.50    --   44.32 -11.00 -30.00   78
 13  ω    -20.00  28.00   0.50    0.50    --   44.32 -21.00 -60.00   96
 14  ω    -19.00  15.00   0.50    0.50    --   44.32 -21.00 120.00   68
 15  ω     29.00  54.00   0.50    0.50    --   44.32  70.00 -99.00   50
 16  ω     77.00 102.00   0.50    0.50    --   44.32  70.00 -99.00   50
 17  ω    -54.00 -28.00   0.50    3.50    --  -93.31  50.00  90.00   52
 18  ω   -127.00-101.00   0.50    3.50    --  -93.31 -25.00-180.00   52
 19  ω   -158.00-131.00   0.50    3.50    --  -93.31 -25.00-180.00   54
 20  ω    -51.00 -26.00   0.50    3.50    --  -93.31  59.00-120.00   50
 21  ω    -61.00 -32.00   0.50    3.50    --  -93.31 117.00   0.00   58
 22  ω   -108.00 -73.00   0.50    3.50    --  -93.31 117.00   0.00   70
 23  ω   -106.00 -38.00   0.50    3.50    --  -93.31  77.00  30.00  136
 24  ω    -80.00 -30.00   0.50    3.50    --  -93.31  68.00  90.00  100
 25  ω   -158.00 -95.00   0.50    3.50    --  -93.31 -68.00  90.00  126
 26  ω     29.00  55.00   0.50    3.50    --   94.87 -50.00-120.00   52
 27  ω     45.00  70.00   0.50    3.50    --   94.87 -68.00  60.00   50
 28  ω    129.00 157.00   0.50    3.50    --   94.87  68.00-150.00   56
 29  ω     93.00 118.00   0.50    3.50    --   94.87  70.00 -99.00   50
 30  ω     73.00 100.00   0.50    3.50    --   94.87  68.00-150.00   54
 31  ω     31.00  56.00   0.50    3.50    --   94.87 -50.00  90.00   50
 32  ω     54.00 105.00   0.50    3.50    --   94.87 -96.00 120.00  102
 33  ω     25.00  51.00   0.50    3.50    --   94.87 -96.00 120.00   52
 34  ω     90.00 163.00   0.50    3.50    --   94.87  25.00 -30.00  146
 35  ω     31.00  56.00   0.50    3.50    --   94.87 -59.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0973157000
_diffrn_orient_matrix_UB_12      -0.0094567000
_diffrn_orient_matrix_UB_13      0.0644624000
_diffrn_orient_matrix_UB_21      0.0517695000
_diffrn_orient_matrix_UB_22      -0.1258220000
_diffrn_orient_matrix_UB_23      0.0170682000
_diffrn_orient_matrix_UB_31      0.1046065000
_diffrn_orient_matrix_UB_32      0.0535525000
_diffrn_orient_matrix_UB_33      0.0514457000
_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  0.0242
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10810
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.402
_diffrn_reflns_theta_min         4.617
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.789
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.57a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.022(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3796
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0260
_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)+(0.0395P)²+0.3485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0688
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3700
_reflns_number_total             3796
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob02052a2.cif
_cod_data_source_block           Sa5fHCl
_cod_depositor_comments
'Adding full bibliography for 7160364--7160367.cif.'
_cod_database_code               7160364
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H N O Cl'
_chemical_oxdiff_usercomment     'DT B'
_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.
;
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.978(13)
 0.022(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, All O(H,H) groups
3.a Free rotating group:
 O1(H1D,H1E)
3.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C20(H20A,H20B), C22(H22A,H22B), C21(H21A,H21B)
3.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C11(H11), C12(H12), C13(H13), C9(H9), C8(H8), C7(H7), C6(H6),
 C15(H15), C17(H17), C16(H16)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_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 1.276
_oxdiff_exptl_absorpt_empirical_full_min 0.804
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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 0.11053(5) 0.65293(4) 0.47787(3) 0.02958(14) Uani 1 1 d . . . . .
N1 N 0.34167(16) 0.37629(14) 0.28711(9) 0.0190(3) Uani 1 1 d . . . . .
N2 N 0.22783(16) 0.46754(14) 0.37328(9) 0.0215(3) Uani 1 1 d . . . . .
H2 H 0.208207 0.504768 0.414180 0.026 Uiso 1 1 calc R U . . .
O1 O 0.20361(18) 0.14463(17) 0.05056(10) 0.0429(4) Uani 1 1 d G . . . .
H1D H 0.124623 0.170131 0.040455 0.064 Uiso 1 1 d G U . . .
H1E H 0.255914 0.198014 0.031902 0.064 Uiso 1 1 d G U . . .
N4 N 0.46019(17) 0.47419(14) 0.38423(9) 0.0205(3) Uani 1 1 d . . . . .
N3 N 0.36572(19) 0.19052(14) 0.38783(9) 0.0257(4) Uani 1 1 d . . . . .
C3 C 0.35029(19) 0.44025(16) 0.35034(11) 0.0193(4) Uani 1 1 d . . . . .
C4 C 0.20771(19) 0.36976(17) 0.26709(11) 0.0208(4) Uani 1 1 d . . . . .
C11 C 0.47379(19) 0.34216(18) 0.18069(11) 0.0223(4) Uani 1 1 d . . . . .
H11 H 0.414519 0.392026 0.154625 0.027 Uiso 1 1 calc R U . . .
C18 C 0.4968(2) 0.18173(16) 0.36245(11) 0.0224(4) Uani 1 1 d . . . . .
C10 C 0.44773(18) 0.31290(17) 0.25203(11) 0.0188(4) Uani 1 1 d . . . . .
C19 C 0.52822(19) 0.23133(16) 0.29202(10) 0.0194(4) Uani 1 1 d . . . . .
C1 C 0.58462(19) 0.49524(18) 0.34523(11) 0.0241(4) Uani 1 1 d . . . . .
H1A H 0.646466 0.430493 0.355861 0.036 Uiso 1 1 calc R U . . .
H1B H 0.622764 0.570983 0.361278 0.036 Uiso 1 1 calc R U . . .
H1C H 0.567677 0.498303 0.292529 0.036 Uiso 1 1 calc R U . . .
C5 C 0.1372(2) 0.42721(17) 0.32169(11) 0.0223(4) Uani 1 1 d . . . . .
C12 C 0.5879(2) 0.29868(18) 0.14589(12) 0.0260(4) Uani 1 1 d . . . . .
H12 H 0.602916 0.313971 0.095497 0.031 Uiso 1 1 calc R U . . .
C14 C 0.6513(2) 0.20095(17) 0.25887(11) 0.0235(4) Uani 1 1 d . . . . .
C13 C 0.6768(2) 0.23414(18) 0.18566(12) 0.0261(4) Uani 1 1 d . . . . .
H13 H 0.757718 0.211020 0.163604 0.031 Uiso 1 1 calc R U . . .
C9 C 0.1475(2) 0.32128(17) 0.20598(11) 0.0242(4) Uani 1 1 d . . . . .
H9 H 0.196224 0.280044 0.169556 0.029 Uiso 1 1 calc R U . . .
C2 C 0.4472(2) 0.52933(19) 0.45672(10) 0.0248(4) Uani 1 1 d . . . . .
H2A H 0.400278 0.605177 0.452152 0.037 Uiso 1 1 calc R U . . .
H2B H 0.535153 0.543454 0.477267 0.037 Uiso 1 1 calc R U . . .
H2C H 0.397669 0.476116 0.489064 0.037 Uiso 1 1 calc R U . . .
C23 C 0.2698(2) 0.11512(18) 0.34769(11) 0.0258(4) Uani 1 1 d . . . . .
H23A H 0.301518 0.031983 0.344443 0.031 Uiso 1 1 calc R U . . .
H23B H 0.255133 0.145963 0.297654 0.031 Uiso 1 1 calc R U . . .
C8 C 0.0112(2) 0.3366(2) 0.20106(12) 0.0297(5) Uani 1 1 d . . . . .
H8 H -0.034467 0.305655 0.159882 0.036 Uiso 1 1 calc R U . . .
C7 C -0.0599(2) 0.3965(2) 0.25540(13) 0.0312(5) Uani 1 1 d . . . . .
H7 H -0.152553 0.405779 0.249857 0.037 Uiso 1 1 calc R U . . .
C6 C 0.0011(2) 0.44263(19) 0.31721(13) 0.0274(4) Uani 1 1 d . . . . .
H6 H -0.047271 0.482477 0.354334 0.033 Uiso 1 1 calc R U . . .
C15 C 0.7476(2) 0.13990(19) 0.30064(13) 0.0309(5) Uani 1 1 d . . . . .
H15 H 0.831384 0.122667 0.279878 0.037 Uiso 1 1 calc R U . . .
C17 C 0.5939(2) 0.12326(18) 0.40061(12) 0.0311(5) Uani 1 1 d . . . . .
H17 H 0.575422 0.093994 0.448245 0.037 Uiso 1 1 calc R U . . .
C20 C 0.3374(3) 0.1666(2) 0.46492(12) 0.0393(6) Uani 1 1 d . . . . .
H20A H 0.379977 0.225762 0.497317 0.047 Uiso 1 1 calc R U . . .
H20B H 0.365810 0.085619 0.479292 0.047 Uiso 1 1 calc R U . . .
C16 C 0.7204(3) 0.1059(2) 0.37034(14) 0.0358(6) Uani 1 1 d . . . . .
H16 H 0.787603 0.069985 0.399065 0.043 Uiso 1 1 calc R U . . .
C22 C 0.1425(3) 0.1225(2) 0.39320(14) 0.0418(6) Uani 1 1 d . . . . .
H22A H 0.104584 0.042429 0.401284 0.050 Uiso 1 1 calc R U . . .
H22B H 0.075938 0.173109 0.368691 0.050 Uiso 1 1 calc R U . . .
C21 C 0.1875(3) 0.1786(2) 0.46591(15) 0.0500(8) Uani 1 1 d . . . . .
H21A H 0.160889 0.263202 0.468660 0.060 Uiso 1 1 calc R U . . .
H21B H 0.149174 0.135442 0.508056 0.060 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'
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_
_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
C3 N1 C4 108.03(16) . . ?
C3 N1 C10 126.19(16) . . ?
C4 N1 C10 125.30(16) . . ?
C3 N2 H2 125.6 . . ?
C3 N2 C5 108.81(17) . . ?
C5 N2 H2 125.6 . . ?
H1D O1 H1E 104.5 . . ?
C3 N4 C1 122.60(16) . . ?
C3 N4 C2 117.82(16) . . ?
C1 N4 C2 116.57(16) . . ?
C18 N3 C23 114.45(16) . . ?
C18 N3 C20 119.27(19) . . ?
C20 N3 C23 104.08(16) . . ?
N2 C3 N1 109.00(17) . . ?
N4 C3 N1 126.84(17) . . ?
N4 C3 N2 124.14(17) . . ?
C5 C4 N1 106.56(17) . . ?
C9 C4 N1 130.92(18) . . ?
C9 C4 C5 122.51(18) . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.35(19) . . ?
C12 C11 H11 119.8 . . ?
N3 C18 C19 118.43(17) . . ?
C17 C18 N3 122.72(19) . . ?
C17 C18 C19 118.8(2) . . ?
C11 C10 N1 116.68(17) . . ?
C11 C10 C19 122.08(18) . . ?
C19 C10 N1 121.02(17) . . ?
C10 C19 C18 125.47(18) . . ?
C14 C19 C18 118.73(18) . . ?
C14 C19 C10 115.77(18) . . ?
N4 C1 H1A 109.5 . . ?
N4 C1 H1B 109.5 . . ?
N4 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C5 C6 130.7(2) . . ?
C4 C5 N2 107.46(17) . . ?
C4 C5 C6 121.7(2) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.02(19) . . ?
C13 C12 H12 120.5 . . ?
C13 C14 C19 119.91(19) . . ?
C13 C14 C15 120.84(19) . . ?
C15 C14 C19 119.24(19) . . ?
C12 C13 C14 121.59(19) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C4 C9 H9 122.0 . . ?
C4 C9 C8 116.08(19) . . ?
C8 C9 H9 122.0 . . ?
N4 C2 H2A 109.5 . . ?
N4 C2 H2B 109.5 . . ?
N4 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N3 C23 H23A 110.8 . . ?
N3 C23 H23B 110.8 . . ?
N3 C23 C22 104.52(17) . . ?
H23A C23 H23B 108.9 . . ?
C22 C23 H23A 110.8 . . ?
C22 C23 H23B 110.8 . . ?
C9 C8 H8 119.2 . . ?
C9 C8 C7 121.5(2) . . ?
C7 C8 H8 119.2 . . ?
C8 C7 H7 119.1 . . ?
C6 C7 C8 121.9(2) . . ?
C6 C7 H7 119.1 . . ?
C5 C6 H6 121.9 . . ?
C7 C6 C5 116.3(2) . . ?
C7 C6 H6 121.9 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C18 C17 H17 119.4 . . ?
C18 C17 C16 121.2(2) . . ?
C16 C17 H17 119.4 . . ?
N3 C20 H20A 111.6 . . ?
N3 C20 H20B 111.6 . . ?
N3 C20 C21 101.0(2) . . ?
H20A C20 H20B 109.4 . . ?
C21 C20 H20A 111.6 . . ?
C21 C20 H20B 111.6 . . ?
C15 C16 C17 120.9(2) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C23 C22 H22A 111.0 . . ?
C23 C22 H22B 111.0 . . ?
C23 C22 C21 104.0(2) . . ?
H22A C22 H22B 109.0 . . ?
C21 C22 H22A 111.0 . . ?
C21 C22 H22B 111.0 . . ?
C20 C21 C22 104.4(2) . . ?
C20 C21 H21A 110.9 . . ?
C20 C21 H21B 110.9 . . ?
C22 C21 H21A 110.9 . . ?
C22 C21 H21B 110.9 . . ?
H21A C21 H21B 108.9 . . ?
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
N1 C3 1.365(3) . ?
N1 C4 1.408(3) . ?
N1 C10 1.440(2) . ?
N2 H2 0.8800 . ?
N2 C3 1.346(3) . ?
N2 C5 1.393(3) . ?
O1 H1D 0.8702 . ?
O1 H1E 0.8703 . ?
N4 C3 1.331(3) . ?
N4 C1 1.468(2) . ?
N4 C2 1.470(2) . ?
N3 C18 1.410(3) . ?
N3 C23 1.484(3) . ?
N3 C20 1.464(3) . ?
C4 C5 1.387(3) . ?
C4 C9 1.385(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.372(3) . ?
C11 C12 1.408(3) . ?
C18 C19 1.440(3) . ?
C18 C17 1.374(3) . ?
C10 C19 1.429(3) . ?
C19 C14 1.429(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C5 C6 1.393(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.367(3) . ?
C14 C13 1.414(3) . ?
C14 C15 1.417(3) . ?
C13 H13 0.9500 . ?
C9 H9 0.9500 . ?
C9 C8 1.396(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C22 1.538(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.400(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.390(3) . ?
C6 H6 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.359(4) . ?
C17 H17 0.9500 . ?
C17 C16 1.411(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.526(4) . ?
C16 H16 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C21 1.541(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.978(13)
2 0.022(13)
