#------------------------------------------------------------------------------
#$Date: 2026-03-05 04:44:10 +0100 (Thu 05 de Mar de 2026) $
#$Revision: 304830 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/17/7251711.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_7251711
loop_
_publ_author_name
'Kataoka, Takayuki'
'Tsuchido, Yoshitaka'
'Kawai, Hidetoshi'
_publ_section_title
;
 Turn-off fluorescence sensing of benzenediols via guest-induced
 π-conjugation switching in bisimidazole-based hydrindacene
 allosteric receptors.
;
_journal_issue                   3
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              2608
_journal_page_last               2614
_journal_paper_doi               10.1039/d5cp04027b
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C38 H38 N4 O8, 2(C H4 O)'
_chemical_formula_sum            'C40 H46 N4 O10'
_chemical_formula_weight         742.81
_chemical_name_common            Bis(benzimidazolyl)hydrindacene
_chemical_name_systematic        Benzimidazolyl_Hydrindacene
_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     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2j23b2
_audit_creation_date             2024-01-15
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_audit_update_record
;
2024-01-16 deposited with the CCDC.	2026-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                104.498(4)
_cell_angle_beta                 101.414(4)
_cell_angle_gamma                96.313(4)
_cell_formula_units_Z            1
_cell_length_a                   7.8829(3)
_cell_length_b                   10.3305(5)
_cell_length_c                   11.6459(6)
_cell_measurement_reflns_used    5278
_cell_measurement_temperature    93
_cell_measurement_theta_max      75.6140
_cell_measurement_theta_min      4.0140
_cell_volume                     887.21(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.91a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.91a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.91a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      93
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     58.00  92.00   0.50    0.12    --   47.66-135.00 -15.00   68
  2  ω     55.00 119.00   0.50    0.50    --  102.75-135.00 -15.00  128
  3  ω     41.00 110.00   0.50    0.50    --  102.75-125.00  90.00  138
  4  ω     82.00 116.00   0.50    0.50    --  102.75-134.00 164.00   68
  5  ω     25.00  96.00   0.50    0.12    --   47.66-134.00 164.00  142
  6  ω     58.00 102.00   0.50    0.50    --  102.75 -94.00-180.00   88
  7  ω     35.00  70.00   0.50    0.50    --  102.75 -61.00 -60.00   70
  8  ω     39.00  64.00   0.50    0.50    --  102.75 -61.00   0.00   50
  9  ω     36.00  71.00   0.50    0.50    --  102.75 -61.00-180.00   70
 10  ω     95.00 171.00   0.50    0.50    --  102.75  15.00-180.00  152
 11  ω     95.00 171.00   0.50    0.50    --  102.75  45.00-120.00  152
 12  ω    116.00 173.00   0.50    0.50    --  102.75  45.00 -90.00  114
 13  ω     62.00 118.00   0.50    0.12    --   47.66  77.00-150.00  112
 14  ω     35.00 117.00   0.50    0.12    --   47.66  57.00 -30.00  164
 15  ω     74.00 118.00   0.50    0.12    --   47.66 135.00  50.00   88
 16  ω     99.00 124.00   0.50    0.50    --  102.75 135.00  50.00   50
 17  ω    119.00 146.00   0.50    0.50    --  102.75 134.00-128.00   54
 18  ω    -66.00 -41.00   0.50    0.50    -- -102.75  61.00-150.00   50
 19  ω    -62.00 -37.00   0.50    0.50    -- -102.75  61.00-180.00   50
 20  ω    -87.00 -55.00   0.50    0.50    -- -102.75  77.00-180.00   64
 21  ω    -95.00 -32.00   0.50    0.50    -- -102.75  77.00-120.00  126
 22  ω    -56.00 -31.00   0.50    0.50    -- -102.75  61.00 -90.00   50
 23  ω    -22.00  26.00   0.50    0.12    --  -47.66  19.00-150.00   96
 24  ω    -23.00  24.00   0.50    0.12    --  -47.66  19.00 -90.00   94
 25  ω    -65.00 -31.00   0.50    0.50    -- -102.75  61.00   0.00   68
 26  ω    -80.00 -54.00   0.50    0.50    -- -102.75  77.00  30.00   52
 27  ω   -110.00 -35.00   0.50    0.50    -- -102.75 125.00 -30.00  150
 28  ω   -117.00 -36.00   0.50    0.50    -- -102.75 134.00-128.00  162
 29  ω    -66.00 -40.00   0.50    0.12    --  -47.66 134.00-128.00   52
 30  ω    -84.00 -58.00   0.50    0.12    --  -47.66 135.00  50.00   52
 31  ω   -119.00 -49.00   0.50    0.50    -- -102.75 135.00  50.00  140
 32  ω   -174.00 -96.00   0.50    0.50    -- -102.75 -15.00 150.00  156
 33  ω   -169.00 -93.00   0.50    0.50    -- -102.75 -45.00  60.00  152
 34  ω   -118.00 -79.00   0.50    0.12    --  -47.66-135.00 -15.00   78
 35  ω   -145.00-120.00   0.50    0.50    -- -102.75-135.00 -15.00   50
 36  ω   -111.00 -85.00   0.50    0.12    --  -47.66-134.00 164.00   52
 37  ω   -145.00-120.00   0.50    0.50    -- -102.75-134.00 164.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0590449000
_diffrn_orient_matrix_UB_12      -0.0870313000
_diffrn_orient_matrix_UB_13      -0.1338284000
_diffrn_orient_matrix_UB_21      0.0259139000
_diffrn_orient_matrix_UB_22      0.1287211000
_diffrn_orient_matrix_UB_23      -0.0429233000
_diffrn_orient_matrix_UB_31      0.1916966000
_diffrn_orient_matrix_UB_32      -0.0164982000
_diffrn_orient_matrix_UB_33      -0.0006819000
_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  0.0846
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10421
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.321
_diffrn_reflns_theta_min         4.033
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.829
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.91a (Rigaku Oxford Diffraction, 2023)
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    1.390
_exptl_crystal_description       block
_exptl_crystal_F_000             394
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0850
_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)+(0.1894P)²+0.0987P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2299
_refine_ls_wR_factor_ref         0.2396
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2949
_reflns_number_total             3526
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cp04027b2.cif
_cod_data_source_block           hyd_BzIm
_cod_original_cell_volume        887.21(7)
_cod_database_code               7251711
_shelx_shelxl_version_number     2019/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.922
_shelx_estimated_absorpt_t_min   0.636
_olex2_refinement_description
;
1. 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) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B), C18(H18A,H18B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C5(H5), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C16(H16A,H16B,H16C)
2.d Idealised tetrahedral OH refined as rotating group:
 O5(H5A)
;
_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 2.072
_oxdiff_exptl_absorpt_empirical_full_min 0.323
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
O4 O 0.2591(2) 0.08229(17) 0.13629(16) 0.0299(4) Uani 1 1 d . . . . .
O3 O 0.1279(2) 0.22318(18) 0.25697(17) 0.0323(5) Uani 1 1 d . . . . .
O5 O 0.6362(2) 0.36698(18) 0.70593(18) 0.0336(5) Uani 1 1 d . . . . .
H5A H 0.735704 0.344081 0.710075 0.050 Uiso 1 1 calc R U . . .
O2 O 0.5825(2) 0.20449(17) 0.34992(17) 0.0299(4) Uani 1 1 d . . . . .
O1 O 0.5668(2) -0.02226(17) 0.30788(18) 0.0320(5) Uani 1 1 d . . . . .
N2 N 0.2799(2) 0.3260(2) 0.72540(19) 0.0260(5) Uani 1 1 d . . . . .
H2 H 0.372473 0.295640 0.704202 0.031 Uiso 1 1 calc R U . . .
N1 N -0.0013(2) 0.33455(19) 0.72951(19) 0.0250(5) Uani 1 1 d . . . . .
C13 C 0.3114(3) 0.0803(2) 0.3422(2) 0.0247(5) Uani 1 1 d . . . . .
C9 C 0.1437(3) 0.0872(2) 0.4953(2) 0.0243(5) Uani 1 1 d . . . . .
C7 C 0.1085(3) 0.2627(2) 0.6792(2) 0.0238(5) Uani 1 1 d . . . . .
C14 C 0.5015(3) 0.0775(2) 0.3301(2) 0.0248(5) Uani 1 1 d . . . . .
C17 C 0.2216(3) 0.1395(2) 0.2432(2) 0.0254(5) Uani 1 1 d . . . . .
C8 C 0.0551(3) 0.1306(2) 0.5880(2) 0.0244(5) Uani 1 1 d . . . . .
C6 C 0.2809(3) 0.4455(2) 0.8109(2) 0.0262(5) Uani 1 1 d . . . . .
C1 C 0.1041(3) 0.4503(2) 0.8126(2) 0.0261(5) Uani 1 1 d . . . . .
C12 C 0.2113(3) -0.0636(2) 0.3241(2) 0.0256(5) Uani 1 1 d . . . . .
H12A H 0.143064 -0.103324 0.238840 0.031 Uiso 1 1 calc R U . . .
H12B H 0.293200 -0.124664 0.345287 0.031 Uiso 1 1 calc R U . . .
C10 C 0.0912(3) -0.0399(2) 0.4110(2) 0.0243(5) Uani 1 1 d . . . . .
C2 C 0.0579(3) 0.5600(2) 0.8907(2) 0.0301(6) Uani 1 1 d . . . . .
H2A H -0.061306 0.564829 0.892242 0.036 Uiso 1 1 calc R U . . .
C11 C 0.3015(3) 0.1639(2) 0.4706(2) 0.0255(5) Uani 1 1 d . . . . .
H11A H 0.409618 0.167698 0.532252 0.031 Uiso 1 1 calc R U . . .
H11B H 0.284463 0.257508 0.470948 0.031 Uiso 1 1 calc R U . . .
C18 C 0.1936(3) 0.1381(3) 0.0363(2) 0.0317(6) Uani 1 1 d . . . . .
H18A H 0.250683 0.233613 0.054604 0.038 Uiso 1 1 calc R U . . .
H18B H 0.065219 0.135322 0.024079 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4166(3) 0.5484(2) 0.8855(2) 0.0313(6) Uani 1 1 d . . . . .
H5 H 0.535768 0.545325 0.882808 0.038 Uiso 1 1 calc R U . . .
C15 C 0.7612(3) 0.2228(3) 0.3306(3) 0.0312(6) Uani 1 1 d . . . . .
H15A H 0.756570 0.217954 0.244001 0.037 Uiso 1 1 calc R U . . .
H15B H 0.823183 0.150433 0.351238 0.037 Uiso 1 1 calc R U . . .
C19 C 0.2355(3) 0.0536(3) -0.0761(3) 0.0366(6) Uani 1 1 d . . . . .
H19A H 0.201182 0.092999 -0.143815 0.055 Uiso 1 1 calc R U . . .
H19B H 0.170753 -0.038927 -0.097139 0.055 Uiso 1 1 calc R U . . .
H19C H 0.361792 0.051558 -0.060894 0.055 Uiso 1 1 calc R U . . .
C20 C 0.6215(3) 0.4661(3) 0.6402(3) 0.0338(6) Uani 1 1 d . . . . .
H20A H 0.591264 0.420827 0.552439 0.051 Uiso 1 1 calc R U . . .
H20B H 0.733654 0.527885 0.661802 0.051 Uiso 1 1 calc R U . . .
H20C H 0.529433 0.517640 0.661263 0.051 Uiso 1 1 calc R U . . .
C16 C 0.8561(3) 0.3584(3) 0.4106(3) 0.0329(6) Uani 1 1 d . . . . .
H16A H 0.789693 0.428866 0.393283 0.049 Uiso 1 1 calc R U . . .
H16B H 0.972891 0.375404 0.394798 0.049 Uiso 1 1 calc R U . . .
H16C H 0.867969 0.359871 0.496336 0.049 Uiso 1 1 calc R U . . .
C3 C 0.1926(3) 0.6616(2) 0.9661(2) 0.0320(6) Uani 1 1 d . . . . .
H3 H 0.164956 0.737089 1.020576 0.038 Uiso 1 1 calc R U . . .
C4 C 0.3682(3) 0.6553(2) 0.9635(2) 0.0327(6) Uani 1 1 d . . . . .
H4 H 0.456985 0.726447 1.016913 0.039 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_
_citation_id
_citation_doi
_citation_year
1 10.1002/cplu.202400612 2025
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 O4 C18 115.88(19) . . ?
C20 O5 H5A 109.5 . . ?
C14 O2 C15 117.48(18) . . ?
C7 N2 H2 126.2 . . ?
C7 N2 C6 107.62(19) . . ?
C6 N2 H2 126.2 . . ?
C7 N1 C1 105.53(19) . . ?
C14 C13 C12 111.77(18) . . ?
C14 C13 C11 112.20(19) . . ?
C17 C13 C14 107.00(19) . . ?
C17 C13 C12 109.19(19) . . ?
C17 C13 C11 111.22(18) . . ?
C12 C13 C11 105.49(19) . . ?
C8 C9 C11 128.0(2) . . ?
C10 C9 C8 121.5(2) . . ?
C10 C9 C11 110.5(2) . . ?
N2 C7 C8 123.63(19) . . ?
N1 C7 N2 111.8(2) . . ?
N1 C7 C8 124.5(2) . . ?
O2 C14 C13 109.03(18) . . ?
O1 C14 O2 125.6(2) . . ?
O1 C14 C13 125.3(2) . . ?
O4 C17 C13 110.33(19) . . ?
O3 C17 O4 124.1(2) . . ?
O3 C17 C13 125.5(2) . . ?
C9 C8 C7 122.9(2) . . ?
C9 C8 C10 116.5(2) . 2_556 ?
C10 C8 C7 120.6(2) 2_556 . ?
N2 C6 C1 105.5(2) . . ?
N2 C6 C5 132.3(2) . . ?
C5 C6 C1 122.2(2) . . ?
N1 C1 C6 109.5(2) . . ?
N1 C1 C2 130.0(2) . . ?
C2 C1 C6 120.4(2) . . ?
C13 C12 H12A 111.1 . . ?
C13 C12 H12B 111.1 . . ?
H12A C12 H12B 109.0 . . ?
C10 C12 C13 103.48(18) . . ?
C10 C12 H12A 111.1 . . ?
C10 C12 H12B 111.1 . . ?
C9 C10 C8 122.0(2) . 2_556 ?
C9 C10 C12 111.10(19) . . ?
C8 C10 C12 126.9(2) 2_556 . ?
C1 C2 H2A 121.2 . . ?
C3 C2 C1 117.5(2) . . ?
C3 C2 H2A 121.2 . . ?
C13 C11 H11A 111.0 . . ?
C13 C11 H11B 111.0 . . ?
C9 C11 C13 103.84(18) . . ?
C9 C11 H11A 111.0 . . ?
C9 C11 H11B 111.0 . . ?
H11A C11 H11B 109.0 . . ?
O4 C18 H18A 110.2 . . ?
O4 C18 H18B 110.2 . . ?
O4 C18 C19 107.5(2) . . ?
H18A C18 H18B 108.5 . . ?
C19 C18 H18A 110.2 . . ?
C19 C18 H18B 110.2 . . ?
C6 C5 H5 121.8 . . ?
C4 C5 C6 116.5(2) . . ?
C4 C5 H5 121.8 . . ?
O2 C15 H15A 110.1 . . ?
O2 C15 H15B 110.1 . . ?
O2 C15 C16 108.19(19) . . ?
H15A C15 H15B 108.4 . . ?
C16 C15 H15A 110.1 . . ?
C16 C15 H15B 110.1 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 122.0(2) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
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
O4 C17 1.343(3) . ?
O4 C18 1.456(3) . ?
O3 C17 1.199(3) . ?
O5 H5A 0.8400 . ?
O5 C20 1.425(3) . ?
O2 C14 1.337(3) . ?
O2 C15 1.470(3) . ?
O1 C14 1.196(3) . ?
N2 H2 0.8800 . ?
N2 C7 1.373(3) . ?
N2 C6 1.377(3) . ?
N1 C7 1.329(3) . ?
N1 C1 1.393(3) . ?
C13 C14 1.535(3) . ?
C13 C17 1.526(3) . ?
C13 C12 1.549(3) . ?
C13 C11 1.550(3) . ?
C9 C8 1.406(3) . ?
C9 C10 1.390(3) . ?
C9 C11 1.516(3) . ?
C7 C8 1.463(3) . ?
C8 C10 1.408(3) 2_556 ?
C6 C1 1.404(3) . ?
C6 C5 1.396(3) . ?
C1 C2 1.396(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C10 1.512(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.387(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.499(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.385(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.493(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C3 H3 0.9500 . ?
C3 C4 1.399(4) . ?
C4 H4 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
_geom_torsion_publ_flag
N2 C7 C8 C9 -34.0(4) . . . . ?
N2 C7 C8 C10 146.4(2) . . . 2_556 ?
N2 C6 C1 N1 0.3(3) . . . . ?
N2 C6 C1 C2 179.9(2) . . . . ?
N2 C6 C5 C4 -179.1(3) . . . . ?
N1 C7 C8 C9 147.6(2) . . . . ?
N1 C7 C8 C10 -31.9(3) . . . 2_556 ?
N1 C1 C2 C3 179.0(2) . . . . ?
C13 C12 C10 C9 -15.9(3) . . . . ?
C13 C12 C10 C8 164.7(2) . . . 2_556 ?
C7 N2 C6 C1 -0.3(3) . . . . ?
C7 N2 C6 C5 179.9(3) . . . . ?
C7 N1 C1 C6 -0.2(3) . . . . ?
C7 N1 C1 C2 -179.8(3) . . . . ?
C14 O2 C15 C16 -152.8(2) . . . . ?
C14 C13 C17 O4 45.7(2) . . . . ?
C14 C13 C17 O3 -135.6(2) . . . . ?
C14 C13 C12 C10 145.2(2) . . . . ?
C14 C13 C11 C9 -143.91(19) . . . . ?
C17 O4 C18 C19 -175.28(19) . . . . ?
C17 C13 C14 O2 62.2(2) . . . . ?
C17 C13 C14 O1 -118.5(3) . . . . ?
C17 C13 C12 C10 -96.6(2) . . . . ?
C17 C13 C11 C9 96.3(2) . . . . ?
C8 C9 C10 C8 1.5(4) . . . 2_556 ?
C8 C9 C10 C12 -178.0(2) . . . . ?
C8 C9 C11 C13 -167.2(2) . . . . ?
C6 N2 C7 N1 0.2(3) . . . . ?
C6 N2 C7 C8 -178.3(2) . . . . ?
C6 C1 C2 C3 -0.6(4) . . . . ?
C6 C5 C4 C3 -1.3(4) . . . . ?
C1 N1 C7 N2 0.0(3) . . . . ?
C1 N1 C7 C8 178.5(2) . . . . ?
C1 C6 C5 C4 1.1(4) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C12 C13 C14 O2 -178.3(2) . . . . ?
C12 C13 C14 O1 1.0(3) . . . . ?
C12 C13 C17 O4 -75.4(2) . . . . ?
C12 C13 C17 O3 103.3(3) . . . . ?
C12 C13 C11 C9 -22.0(2) . . . . ?
C10 C9 C8 C7 179.0(2) . . . . ?
C10 C9 C8 C10 -1.4(4) . . . 2_556 ?
C10 C9 C11 C13 12.8(3) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C11 C13 C14 O2 -60.0(3) . . . . ?
C11 C13 C14 O1 119.3(3) . . . . ?
C11 C13 C17 O4 168.61(17) . . . . ?
C11 C13 C17 O3 -12.7(3) . . . . ?
C11 C13 C12 C10 23.0(2) . . . . ?
C11 C9 C8 C7 -0.9(4) . . . . ?
C11 C9 C8 C10 178.7(2) . . . 2_556 ?
C11 C9 C10 C8 -178.6(2) . . . 2_556 ?
C11 C9 C10 C12 1.9(3) . . . . ?
C18 O4 C17 O3 6.4(3) . . . . ?
C18 O4 C17 C13 -174.93(17) . . . . ?
C5 C6 C1 N1 -179.9(2) . . . . ?
C5 C6 C1 C2 -0.2(4) . . . . ?
C15 O2 C14 O1 6.6(4) . . . . ?
C15 O2 C14 C13 -174.1(2) . . . . ?
