#------------------------------------------------------------------------------
#$Date: 2026-03-26 03:07:53 +0100 (Thu 26 de Mar de 2026) $
#$Revision: 305183 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/10/7161093.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_7161093
loop_
_publ_author_name
'Xu, Fen'
'Zhang, Shi-Yu'
'Huo, Jia-Qi'
'Zeng, Fan-Wang'
'Zhou, Fu-Kang'
'Barboni, Luciano'
_publ_section_title
;
 Rh(III)-Catalyzed Cascade C-H Activation/Amination Enables the Synthesis
 of 1,2-Disubstituted Benzimidazoles from Amidines and Arynes
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D6OB00074F
_journal_year                    2025
_chemical_formula_moiety         'C20 H17 N2 O, C20 H17 N3'
_chemical_formula_sum            'C40 H34 N5 O'
_chemical_formula_weight         600.72
_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
_audit_creation_date             2026-01-14
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2026-01-14 deposited with the CCDC.	2026-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.504(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.2779(13)
_cell_length_b                   11.148(2)
_cell_length_c                   22.875(5)
_cell_measurement_reflns_used    7205
_cell_measurement_temperature    131.9(2)
_cell_measurement_theta_max      25.1000
_cell_measurement_theta_min      3.2250
_cell_volume                     1587.2(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      131.9(2)
_diffrn_detector_area_resol_mean 16.2116
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   87.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0372   77.0000  120.0000 99

#__ type_ start__ end____ width___ exp.time_
  2 omega  -10.00   16.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0372  -57.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -20.00   60.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0372  -99.0000 -120.0000 80

#__ type_ start__ end____ width___ exp.time_
  4 omega  -46.00    7.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0372  -77.0000   90.0000 53

#__ type_ start__ end____ width___ exp.time_
  5 omega  -12.00   21.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0372   77.0000   30.0000 33

#__ type_ start__ end____ width___ exp.time_
  6 omega  -26.00   44.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0372  -37.0000  -30.0000 70

#__ type_ start__ end____ width___ exp.time_
  7 omega    2.00   43.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0372   57.0000 -120.0000 41

#__ type_ start__ end____ width___ exp.time_
  8 omega   11.00   37.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0372   57.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega  -64.00  -35.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.8185 -178.0000 -180.0000 29

#__ type_ start__ end____ width___ exp.time_
 10 omega  -88.00  -18.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.8185  -77.0000  -30.0000 70
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0412144000
_diffrn_orient_matrix_UB_12      -0.0304618000
_diffrn_orient_matrix_UB_13      -0.0075915000
_diffrn_orient_matrix_UB_21      -0.0215789000
_diffrn_orient_matrix_UB_22      0.0113226000
_diffrn_orient_matrix_UB_23      0.0245186000
_diffrn_orient_matrix_UB_31      -0.0193623000
_diffrn_orient_matrix_UB_32      0.0210923000
_diffrn_orient_matrix_UB_33      -0.0202106000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9373
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.827
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       block
_exptl_crystal_F_000             634
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       0.059(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         5439
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.1706
_refine_ls_R_factor_gt           0.1327
_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)+(0.1266P)²+8.3833P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3759
_refine_ls_wR_factor_ref         0.4017
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3503
_reflns_number_total             5439
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6ob00074f2.cif
_cod_data_source_block           260111lu_yq_zz_0773097_zcs_0m
_cod_database_code               7161093
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C Zn'
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 O1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C18(H18), C19(H19), N004(H004), C00K(H00K),
 C00M(H00M), C00P(H00P), C00Q(H00Q), C00S(H00S), C00T(H00T), C00Y(H00Y),
 C011(H011), C012(H012), C013(H013), C015(H015), C016(H016), C018(H018)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C019(H01A,H01B,H01C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.4008(14) 0.0890(6) 0.4046(3) 0.090(2) Uani 1 1 d . . . . .
H1 H 0.293185 0.028732 0.398693 0.108 Uiso 1 1 calc R U . . .
N1 N 0.4298(11) 0.3658(6) 0.6077(3) 0.0539(16) Uani 1 1 d . . . . .
N2 N 0.5389(12) 0.4643(6) 0.6925(3) 0.0604(18) Uani 1 1 d . . . . .
C1 C 0.2791(13) 0.4547(7) 0.6126(3) 0.0501(18) Uani 1 1 d . . . . .
C2 C 0.0939(14) 0.4833(8) 0.5760(4) 0.060(2) Uani 1 1 d . . . . .
H2 H 0.049102 0.439959 0.540731 0.072 Uiso 1 1 calc R U . . .
C3 C -0.0235(16) 0.5798(9) 0.5938(4) 0.071(2) Uani 1 1 d . . . . .
H3 H -0.152888 0.603197 0.570350 0.085 Uiso 1 1 calc R U . . .
C4 C 0.0450(17) 0.6418(9) 0.6451(4) 0.072(3) Uani 1 1 d . . . . .
H4 H -0.038161 0.707795 0.655537 0.087 Uiso 1 1 calc R U . . .
C5 C 0.2291(15) 0.6118(8) 0.6817(4) 0.063(2) Uani 1 1 d . . . . .
H5 H 0.273288 0.655795 0.716720 0.075 Uiso 1 1 calc R U . . .
C6 C 0.3468(13) 0.5160(7) 0.6657(3) 0.0529(19) Uani 1 1 d . . . . .
C7 C 0.5812(13) 0.3745(7) 0.6578(3) 0.055(2) Uani 1 1 d . . . . .
C8 C 0.7673(13) 0.2949(7) 0.6709(3) 0.0529(19) Uani 1 1 d . . . . .
C9 C 0.7701(15) 0.1777(8) 0.6510(4) 0.064(2) Uani 1 1 d . . . . .
H9 H 0.650520 0.145749 0.626087 0.076 Uiso 1 1 calc R U . . .
C10 C 0.9523(16) 0.1067(9) 0.6681(4) 0.075(3) Uani 1 1 d . . . . .
H10 H 0.953941 0.026508 0.654105 0.090 Uiso 1 1 calc R U . . .
C11 C 1.1219(16) 0.1470(9) 0.7030(4) 0.070(2) Uani 1 1 d . . . . .
H11 H 1.241105 0.095816 0.714464 0.084 Uiso 1 1 calc R U . . .
C12 C 1.1239(16) 0.2675(10) 0.7232(4) 0.076(3) Uani 1 1 d . . . . .
H12 H 1.245281 0.298471 0.747682 0.091 Uiso 1 1 calc R U . . .
C13 C 0.9457(14) 0.3393(8) 0.7066(4) 0.063(2) Uani 1 1 d . . . . .
H13 H 0.945758 0.420055 0.719826 0.076 Uiso 1 1 calc R U . . .
C14 C 0.4281(13) 0.2903(7) 0.5556(3) 0.0501(18) Uani 1 1 d . . . . .
C15 C 0.2766(16) 0.2025(8) 0.5441(4) 0.066(2) Uani 1 1 d . . . . .
H15 H 0.175489 0.187137 0.570673 0.079 Uiso 1 1 calc R U . . .
C16 C 0.2740(17) 0.1357(8) 0.4921(4) 0.073(3) Uani 1 1 d . . . . .
H16 H 0.170854 0.073716 0.483509 0.088 Uiso 1 1 calc R U . . .
C17 C 0.4199(15) 0.1589(7) 0.4532(4) 0.061(2) Uani 1 1 d . . . . .
C18 C 0.5668(15) 0.2468(8) 0.4652(4) 0.064(2) Uani 1 1 d . . . . .
H18 H 0.668654 0.262123 0.438877 0.077 Uiso 1 1 calc R U . . .
C19 C 0.5689(15) 0.3160(8) 0.5169(4) 0.061(2) Uani 1 1 d . . . . .
H19 H 0.668179 0.380118 0.524682 0.073 Uiso 1 1 calc R U . . .
C20 C 0.545(2) 0.1073(11) 0.3625(5) 0.097(4) Uani 1 1 d . . . . .
H20A H 0.505972 0.053856 0.328742 0.146 Uiso 1 1 calc R U . . .
H20B H 0.691583 0.089906 0.380507 0.146 Uiso 1 1 calc R U . . .
H20C H 0.535471 0.190877 0.349054 0.146 Uiso 1 1 calc R U . . .
N001 N 0.5709(11) 0.8653(6) 0.8919(3) 0.0548(17) Uani 1 1 d . . . . .
N002 N 0.4622(11) 0.9631(6) 0.8075(3) 0.0587(18) Uani 1 1 d . . . . .
N004 N 0.5997(14) 0.5897(6) 1.0956(3) 0.068(2) Uani 1 1 d . . . . .
H004 H 0.700609 0.534702 1.101778 0.082 Uiso 1 1 calc R U . . .
C00A C 0.2324(13) 0.7952(7) 0.8285(3) 0.0525(19) Uani 1 1 d . . . . .
C00E C 0.4203(13) 0.8737(7) 0.8423(3) 0.055(2) Uani 1 1 d . . . . .
C00H C 0.6512(13) 1.0151(7) 0.8351(3) 0.0527(19) Uani 1 1 d . . . . .
C00J C 0.5821(15) 0.6589(8) 1.0462(4) 0.062(2) Uani 1 1 d . . . . .
C00K C 0.9069(14) 0.9834(8) 0.9240(4) 0.060(2) Uani 1 1 d . . . . .
H00K H 0.952439 0.940389 0.959305 0.072 Uiso 1 1 calc R U . . .
C00M C 0.4313(14) 0.8160(8) 0.9835(4) 0.060(2) Uani 1 1 d . . . . .
H00M H 0.332408 0.880300 0.975672 0.072 Uiso 1 1 calc R U . . .
C00P C 0.2300(15) 0.6774(8) 0.8485(4) 0.063(2) Uani 1 1 d . . . . .
H00P H 0.349907 0.645907 0.873405 0.076 Uiso 1 1 calc R U . . .
C00Q C 0.7731(15) 1.1118(8) 0.8186(4) 0.062(2) Uani 1 1 d . . . . .
H00Q H 0.729398 1.154924 0.783238 0.075 Uiso 1 1 calc R U . . .
C00S C 0.4325(15) 0.7485(8) 1.0343(4) 0.066(2) Uani 1 1 d . . . . .
H00S H 0.330925 0.764090 1.060756 0.079 Uiso 1 1 calc R U . . .
C00T C 0.7211(16) 0.7025(8) 0.9560(4) 0.069(2) Uani 1 1 d . . . . .
H00T H 0.820156 0.686292 0.928947 0.083 Uiso 1 1 calc R U . . .
C00Y C 0.7277(17) 0.6365(8) 1.0076(4) 0.073(3) Uani 1 1 d . . . . .
H00Y H 0.833157 0.575712 1.016304 0.088 Uiso 1 1 calc R U . . .
C007 C 0.5722(13) 0.7902(7) 0.9445(3) 0.0517(19) Uani 1 1 d . . . . .
C009 C 0.7194(13) 0.9538(7) 0.8870(3) 0.0509(18) Uani 1 1 d . . . . .
C011 C 0.0541(14) 0.8397(8) 0.7928(4) 0.065(2) Uani 1 1 d . . . . .
H011 H 0.052793 0.920348 0.779422 0.077 Uiso 1 1 calc R U . . .
C012 C 1.0227(15) 1.0801(8) 0.9060(4) 0.066(2) Uani 1 1 d . . . . .
H012 H 1.151268 1.104122 0.929700 0.079 Uiso 1 1 calc R U . . .
C013 C 0.0494(16) 0.6059(9) 0.8316(4) 0.071(2) Uani 1 1 d . . . . .
H013 H 0.048154 0.525591 0.845451 0.085 Uiso 1 1 calc R U . . .
C015 C -0.1227(17) 0.6479(10) 0.7963(4) 0.074(3) Uani 1 1 d . . . . .
H015 H -0.242652 0.597255 0.784817 0.089 Uiso 1 1 calc R U . . .
C016 C -0.1234(15) 0.7659(10) 0.7768(4) 0.075(3) Uani 1 1 d . . . . .
H016 H -0.245290 0.796475 0.752346 0.089 Uiso 1 1 calc R U . . .
C018 C 0.9555(17) 1.1424(9) 0.8543(4) 0.075(3) Uani 1 1 d . . . . .
H018 H 1.038901 1.208063 0.843649 0.090 Uiso 1 1 calc R U . . .
C019 C 0.455(2) 0.6074(11) 1.1367(5) 0.102(4) Uani 1 1 d . . . . .
H01A H 0.309203 0.586581 1.118533 0.153 Uiso 1 1 calc R U . . .
H01B H 0.458100 0.691740 1.148900 0.153 Uiso 1 1 calc R U . . .
H01C H 0.495290 0.556356 1.171178 0.153 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C17 O1 H1 120.6 . . ?
C17 O1 C20 118.7(8) . . ?
C20 O1 H1 120.6 . . ?
C1 N1 C7 106.5(6) . . ?
C1 N1 C14 123.1(6) . . ?
C7 N1 C14 130.1(7) . . ?
C7 N2 C6 106.1(7) . . ?
N1 C1 C6 106.5(7) . . ?
C2 C1 N1 130.3(7) . . ?
C2 C1 C6 123.2(8) . . ?
C1 C2 H2 122.1 . . ?
C1 C2 C3 115.8(8) . . ?
C3 C2 H2 122.1 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(9) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 118.7 . . ?
C5 C4 C3 122.5(8) . . ?
C5 C4 H4 118.7 . . ?
C4 C5 H5 121.1 . . ?
C6 C5 C4 117.8(8) . . ?
C6 C5 H5 121.1 . . ?
N2 C6 C1 108.8(7) . . ?
C5 C6 N2 131.7(8) . . ?
C5 C6 C1 119.5(8) . . ?
N1 C7 C8 124.4(7) . . ?
N2 C7 N1 112.1(7) . . ?
N2 C7 C8 123.4(7) . . ?
C9 C8 C7 123.2(7) . . ?
C9 C8 C13 119.1(8) . . ?
C13 C8 C7 117.6(7) . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 119.0(8) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 118.7 . . ?
C11 C10 C9 122.6(10) . . ?
C11 C10 H10 118.7 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.3(9) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.0(9) . . ?
C13 C12 H12 120.5 . . ?
C8 C13 H13 119.5 . . ?
C12 C13 C8 121.0(9) . . ?
C12 C13 H13 119.5 . . ?
C15 C14 N1 120.1(7) . . ?
C19 C14 N1 118.3(7) . . ?
C19 C14 C15 121.3(7) . . ?
C14 C15 H15 120.8 . . ?
C14 C15 C16 118.4(9) . . ?
C16 C15 H15 120.8 . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.8(8) . . ?
C17 C16 H16 119.6 . . ?
O1 C17 C16 115.3(8) . . ?
C18 C17 O1 124.8(9) . . ?
C18 C17 C16 119.9(8) . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 119.9(9) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 C18 119.7(8) . . ?
C14 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C00E N001 C007 130.0(7) . . ?
C009 N001 C00E 106.5(6) . . ?
C009 N001 C007 123.1(6) . . ?
C00E N002 C00H 105.4(6) . . ?
C00J N004 H004 120.5 . . ?
C00J N004 C019 119.1(8) . . ?
C019 N004 H004 120.5 . . ?
C00P C00A C00E 122.3(7) . . ?
C011 C00A C00E 118.5(7) . . ?
C011 C00A C00P 119.2(8) . . ?
N001 C00E C00A 125.5(7) . . ?
N002 C00E N001 112.0(7) . . ?
N002 C00E C00A 122.4(7) . . ?
N002 C00H C00Q 131.3(7) . . ?
C009 C00H N002 109.3(7) . . ?
C009 C00H C00Q 119.4(8) . . ?
N004 C00J C00S 123.8(9) . . ?
N004 C00J C00Y 116.2(8) . . ?
C00S C00J C00Y 120.0(8) . . ?
C009 C00K H00K 122.1 . . ?
C012 C00K H00K 122.1 . . ?
C012 C00K C009 115.7(8) . . ?
C00S C00M H00M 120.0 . . ?
C007 C00M H00M 120.0 . . ?
C007 C00M C00S 120.1(8) . . ?
C00A C00P H00P 120.3 . . ?
C00A C00P C013 119.4(8) . . ?
C013 C00P H00P 120.3 . . ?
C00H C00Q H00Q 120.7 . . ?
C018 C00Q C00H 118.5(8) . . ?
C018 C00Q H00Q 120.7 . . ?
C00J C00S C00M 119.3(9) . . ?
C00J C00S H00S 120.3 . . ?
C00M C00S H00S 120.3 . . ?
C00Y C00T H00T 120.3 . . ?
C007 C00T H00T 120.3 . . ?
C007 C00T C00Y 119.4(9) . . ?
C00J C00Y C00T 120.1(9) . . ?
C00J C00Y H00Y 119.9 . . ?
C00T C00Y H00Y 119.9 . . ?
C00M C007 N001 118.8(7) . . ?
C00T C007 N001 120.1(8) . . ?
C00T C007 C00M 121.0(7) . . ?
N001 C009 C00H 106.6(7) . . ?
N001 C009 C00K 130.4(7) . . ?
C00H C009 C00K 122.9(8) . . ?
C00A C011 H011 120.0 . . ?
C00A C011 C016 120.0(9) . . ?
C016 C011 H011 120.0 . . ?
C00K C012 H012 119.1 . . ?
C018 C012 C00K 121.8(9) . . ?
C018 C012 H012 119.1 . . ?
C00P C013 H013 119.1 . . ?
C015 C013 C00P 121.7(9) . . ?
C015 C013 H013 119.1 . . ?
C013 C015 H015 120.3 . . ?
C013 C015 C016 119.4(9) . . ?
C016 C015 H015 120.3 . . ?
C011 C016 H016 119.8 . . ?
C015 C016 C011 120.3(9) . . ?
C015 C016 H016 119.8 . . ?
C00Q C018 C012 121.6(9) . . ?
C00Q C018 H018 119.2 . . ?
C012 C018 H018 119.2 . . ?
N004 C019 H01A 109.5 . . ?
N004 C019 H01B 109.5 . . ?
N004 C019 H01C 109.5 . . ?
H01A C019 H01B 109.5 . . ?
H01A C019 H01C 109.5 . . ?
H01B C019 H01C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.9500 . ?
O1 C17 1.351(10) . ?
O1 C20 1.418(13) . ?
N1 C1 1.385(10) . ?
N1 C7 1.393(9) . ?
N1 C14 1.458(9) . ?
N2 C6 1.404(10) . ?
N2 C7 1.326(10) . ?
C1 C2 1.379(11) . ?
C1 C6 1.411(11) . ?
C2 H2 0.9500 . ?
C2 C3 1.396(12) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(13) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(13) . ?
C5 H5 0.9500 . ?
C5 C6 1.374(11) . ?
C7 C8 1.467(11) . ?
C8 C9 1.385(11) . ?
C8 C13 1.388(11) . ?
C9 H9 0.9500 . ?
C9 C10 1.404(13) . ?
C10 H10 0.9500 . ?
C10 C11 1.323(13) . ?
C11 H11 0.9500 . ?
C11 C12 1.420(14) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(13) . ?
C13 H13 0.9500 . ?
C14 C15 1.366(11) . ?
C14 C19 1.361(11) . ?
C15 H15 0.9500 . ?
C15 C16 1.402(12) . ?
C16 H16 0.9500 . ?
C16 C17 1.381(13) . ?
C17 C18 1.349(12) . ?
C18 H18 0.9500 . ?
C18 C19 1.410(12) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N001 C00E 1.381(10) . ?
N001 C007 1.466(9) . ?
N001 C009 1.372(10) . ?
N002 C00E 1.323(10) . ?
N002 C00H 1.395(10) . ?
N004 H004 0.8800 . ?
N004 C00J 1.360(10) . ?
N004 C019 1.405(14) . ?
C00A C00E 1.469(12) . ?
C00A C00P 1.392(12) . ?
C00A C011 1.387(11) . ?
C00H C00Q 1.402(12) . ?
C00H C009 1.389(10) . ?
C00J C00S 1.374(12) . ?
C00J C00Y 1.374(13) . ?
C00K H00K 0.9500 . ?
C00K C009 1.397(11) . ?
C00K C012 1.393(12) . ?
C00M H00M 0.9500 . ?
C00M C00S 1.385(11) . ?
C00M C007 1.366(12) . ?
C00P H00P 0.9500 . ?
C00P C013 1.399(13) . ?
C00Q H00Q 0.9500 . ?
C00Q C018 1.361(13) . ?
C00S H00S 0.9500 . ?
C00T H00T 0.9500 . ?
C00T C00Y 1.387(12) . ?
C00T C007 1.355(11) . ?
C00Y H00Y 0.9500 . ?
C011 H011 0.9500 . ?
C011 C016 1.395(13) . ?
C012 H012 0.9500 . ?
C012 C018 1.388(13) . ?
C013 H013 0.9500 . ?
C013 C015 1.346(13) . ?
C015 H015 0.9500 . ?
C015 C016 1.389(14) . ?
C016 H016 0.9500 . ?
C018 H018 0.9500 . ?
C019 H01A 0.9800 . ?
C019 H01B 0.9800 . ?
C019 H01C 0.9800 . ?
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
_geom_torsion_publ_flag
O1 C17 C18 C19 178.7(8) . . . . ?
N1 C1 C2 C3 -179.8(8) . . . . ?
N1 C1 C6 N2 0.4(9) . . . . ?
N1 C1 C6 C5 178.6(7) . . . . ?
N1 C7 C8 C9 -28.0(12) . . . . ?
N1 C7 C8 C13 154.1(8) . . . . ?
N1 C14 C15 C16 177.0(8) . . . . ?
N1 C14 C19 C18 -178.1(7) . . . . ?
N2 C7 C8 C9 152.6(8) . . . . ?
N2 C7 C8 C13 -25.3(12) . . . . ?
C1 N1 C7 N2 -1.8(9) . . . . ?
C1 N1 C7 C8 178.7(7) . . . . ?
C1 N1 C14 C15 -73.0(10) . . . . ?
C1 N1 C14 C19 101.9(9) . . . . ?
C1 C2 C3 C4 0.3(13) . . . . ?
C2 C1 C6 N2 179.5(7) . . . . ?
C2 C1 C6 C5 -2.3(12) . . . . ?
C2 C3 C4 C5 -0.9(15) . . . . ?
C3 C4 C5 C6 -0.1(14) . . . . ?
C4 C5 C6 N2 179.3(8) . . . . ?
C4 C5 C6 C1 1.6(12) . . . . ?
C6 N2 C7 N1 2.0(9) . . . . ?
C6 N2 C7 C8 -178.5(7) . . . . ?
C6 C1 C2 C3 1.3(12) . . . . ?
C7 N1 C1 C2 -178.2(8) . . . . ?
C7 N1 C1 C6 0.8(8) . . . . ?
C7 N1 C14 C15 113.9(10) . . . . ?
C7 N1 C14 C19 -71.3(11) . . . . ?
C7 N2 C6 C1 -1.5(9) . . . . ?
C7 N2 C6 C5 -179.4(9) . . . . ?
C7 C8 C9 C10 -177.1(8) . . . . ?
C7 C8 C13 C12 176.9(8) . . . . ?
C8 C9 C10 C11 0.5(14) . . . . ?
C9 C8 C13 C12 -1.1(13) . . . . ?
C9 C10 C11 C12 -1.5(15) . . . . ?
C10 C11 C12 C13 1.2(14) . . . . ?
C11 C12 C13 C8 0.1(13) . . . . ?
C13 C8 C9 C10 0.8(13) . . . . ?
C14 N1 C1 C2 7.3(13) . . . . ?
C14 N1 C1 C6 -173.7(7) . . . . ?
C14 N1 C7 N2 172.2(7) . . . . ?
C14 N1 C7 C8 -7.3(13) . . . . ?
C14 C15 C16 C17 -0.6(14) . . . . ?
C15 C14 C19 C18 -3.4(13) . . . . ?
C15 C16 C17 O1 -179.7(9) . . . . ?
C15 C16 C17 C18 0.0(14) . . . . ?
C16 C17 C18 C19 -1.0(14) . . . . ?
C17 C18 C19 C14 2.7(13) . . . . ?
C19 C14 C15 C16 2.3(13) . . . . ?
C20 O1 C17 C16 180.0(9) . . . . ?
C20 O1 C17 C18 0.3(14) . . . . ?
N002 C00H C00Q C018 -179.1(9) . . . . ?
N002 C00H C009 N001 -0.9(9) . . . . ?
N002 C00H C009 C00K 178.9(7) . . . . ?
N004 C00J C00S C00M 178.3(9) . . . . ?
N004 C00J C00Y C00T 179.8(9) . . . . ?
C00A C00P C013 C015 0.1(14) . . . . ?
C00A C011 C016 C015 0.1(14) . . . . ?
C00E N001 C007 C00M -70.9(11) . . . . ?
C00E N001 C007 C00T 113.7(10) . . . . ?
C00E N001 C009 C00H 1.4(9) . . . . ?
C00E N001 C009 C00K -178.3(8) . . . . ?
C00E N002 C00H C00Q 179.2(9) . . . . ?
C00E N002 C00H C009 0.0(9) . . . . ?
C00E C00A C00P C013 -177.3(8) . . . . ?
C00E C00A C011 C016 177.2(8) . . . . ?
C00H N002 C00E N001 0.9(9) . . . . ?
C00H N002 C00E C00A -179.7(7) . . . . ?
C00H C00Q C018 C012 0.3(15) . . . . ?
C00K C012 C018 C00Q -0.2(16) . . . . ?
C00P C00A C00E N001 -27.9(12) . . . . ?
C00P C00A C00E N002 152.7(8) . . . . ?
C00P C00A C011 C016 -1.1(13) . . . . ?
C00P C013 C015 C016 -1.1(15) . . . . ?
C00Q C00H C009 N001 179.8(7) . . . . ?
C00Q C00H C009 C00K -0.4(12) . . . . ?
C00S C00J C00Y C00T -1.4(15) . . . . ?
C00S C00M C007 N001 -178.3(8) . . . . ?
C00S C00M C007 C00T -3.0(14) . . . . ?
C00Y C00J C00S C00M -0.4(14) . . . . ?
C00Y C00T C007 N001 176.5(8) . . . . ?
C00Y C00T C007 C00M 1.2(14) . . . . ?
C007 N001 C00E N002 171.7(7) . . . . ?
C007 N001 C00E C00A -7.7(13) . . . . ?
C007 N001 C009 C00H -172.4(7) . . . . ?
C007 N001 C009 C00K 7.9(13) . . . . ?
C007 C00M C00S C00J 2.6(14) . . . . ?
C007 C00T C00Y C00J 1.0(15) . . . . ?
C009 N001 C00E N002 -1.4(9) . . . . ?
C009 N001 C00E C00A 179.2(7) . . . . ?
C009 N001 C007 C00M 101.3(10) . . . . ?
C009 N001 C007 C00T -74.1(11) . . . . ?
C009 C00H C00Q C018 0.0(13) . . . . ?
C009 C00K C012 C018 -0.2(14) . . . . ?
C011 C00A C00E N001 153.9(8) . . . . ?
C011 C00A C00E N002 -25.5(12) . . . . ?
C011 C00A C00P C013 1.0(13) . . . . ?
C012 C00K C009 N001 -179.8(8) . . . . ?
C012 C00K C009 C00H 0.5(12) . . . . ?
C013 C015 C016 C011 1.0(14) . . . . ?
C019 N004 C00J C00S 1.8(14) . . . . ?
C019 N004 C00J C00Y -179.5(10) . . . . ?
