#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/51/4025170.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_4025170
loop_
_publ_author_name
'Jan Kočí'
'Allen G. Oliver'
'Viktor Krchňák'
_publ_contact_author_address
;
Department of Chemistry and Biochemistry,
University of Notre Dame,
Notre Dame, IN 46556
USA
;
_publ_contact_author_email       viktor.krchnak.1@nd.edu
_publ_contact_author_fax         '+1 574 631 6652'
_publ_contact_author_name        'Viktor Krchnak'
_publ_contact_author_phone       '+1 574 631 5113'
_publ_section_title
;
 Unprecedented Rearrangement of
 2-(2-Aminoethyl)-1-aryl-3,4-dihydropyrazino[1,2-b]indazole-2-ium 6-oxides
 to 2,3-Dihydro-1H-imidazo[1,2-b]indazoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              502
_journal_page_last               505
_journal_paper_doi               10.1021/jo902301x
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C19 H20 N4 O'
_chemical_formula_sum            'C19 H20 N4 O'
_chemical_formula_weight         320.39
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.389(3)
_cell_angle_beta                 95.731(3)
_cell_angle_gamma                104.216(3)
_cell_formula_units_Z            4
_cell_length_a                   7.6124(4)
_cell_length_b                   12.5446(7)
_cell_length_c                   17.6687(9)
_cell_measurement_reflns_used    4277
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      3.65
_cell_volume                     1621.29(15)
_computing_cell_refinement       'Bruker SAINT v7.53A'
_computing_data_collection       'Bruker APEX-II v2008-6'
_computing_data_reduction        'Bruker SAINT v7.53A'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.607
_diffrn_measured_fraction_theta_max 0.607
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13582
_diffrn_reflns_theta_full        68.36
_diffrn_reflns_theta_max         68.36
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  0.9421
_exptl_absorpt_correction_T_min  0.8611
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS, Sheldrick, 2008'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         3623
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0871P)²+0.5481P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1382
_reflns_number_gt                2981
_reflns_number_total             3623
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902301x_si_001.cif
_cod_data_source_block           koci1
_cod_database_code               4025170
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9337(3) 0.79223(17) 0.21633(11) 0.0413(6) Uani 1 1 d . . .
N1 N 0.6515(3) 0.45669(19) -0.08390(12) 0.0344(7) Uani 1 1 d . . .
N2 N 0.6683(3) 0.42739(19) -0.01009(13) 0.0333(7) Uani 1 1 d . . .
N3 N 0.8025(3) 0.46162(19) 0.10917(13) 0.0366(7) Uani 1 1 d . . .
N4 N 0.6832(3) 0.6487(2) 0.18844(13) 0.0353(7) Uani 1 1 d . . .
H4 H 0.575(4) 0.625(3) 0.1604(17) 0.042 Uiso 1 1 d . . .
C1 C 0.5957(4) 0.3227(2) 0.02194(15) 0.0348(8) Uani 1 1 d . . .
H1A H 0.6432 0.2627 -0.0003 0.042 Uiso 1 1 calc R . .
H1B H 0.4606 0.3008 0.0144 0.042 Uiso 1 1 calc R . .
C2 C 0.6702(4) 0.3536(2) 0.10747(16) 0.0351(8) Uani 1 1 d . . .
H2A H 0.5704 0.3590 0.1383 0.042 Uiso 1 1 calc R . .
H2B H 0.7305 0.2979 0.1276 0.042 Uiso 1 1 calc R . .
C3 C 0.7801(4) 0.5017(2) 0.04029(15) 0.0302(8) Uani 1 1 d . . .
C4 C 0.8446(4) 0.5953(2) 0.00108(16) 0.0307(8) Uani 1 1 d . . .
C5 C 0.9554(4) 0.7026(2) 0.02105(17) 0.0366(8) Uani 1 1 d . . .
H5A H 1.0110 0.7252 0.0719 0.044 Uiso 1 1 calc R . .
C6 C 0.9810(4) 0.7740(3) -0.03540(17) 0.0386(8) Uani 1 1 d . . .
H6A H 1.0533 0.8474 -0.0230 0.046 Uiso 1 1 calc R . .
C7 C 0.9016(4) 0.7401(2) -0.11144(16) 0.0372(8) Uani 1 1 d . . .
H7A H 0.9243 0.7912 -0.1491 0.045 Uiso 1 1 calc R . .
C8 C 0.7929(4) 0.6361(2) -0.13279(16) 0.0346(8) Uani 1 1 d . . .
H8A H 0.7411 0.6147 -0.1843 0.041 Uiso 1 1 calc R . .
C9 C 0.7601(4) 0.5612(2) -0.07527(16) 0.0303(8) Uani 1 1 d . . .
C10 C 0.8927(4) 0.5248(2) 0.17924(16) 0.0363(8) Uani 1 1 d . . .
H10A H 0.9914 0.5865 0.1668 0.044 Uiso 1 1 calc R . .
H10B H 0.9501 0.4770 0.2108 0.044 Uiso 1 1 calc R . .
C11 C 0.7679(4) 0.5717(2) 0.22619(16) 0.0357(9) Uani 1 1 d . . .
H11A H 0.6708 0.5097 0.2396 0.043 Uiso 1 1 calc R . .
H11B H 0.8396 0.6093 0.2744 0.043 Uiso 1 1 calc R . .
C12 C 0.7714(4) 0.7571(2) 0.19002(15) 0.0331(8) Uani 1 1 d . . .
C13 C 0.6615(4) 0.8323(2) 0.16097(15) 0.0304(8) Uani 1 1 d . . .
C14 C 0.7518(4) 0.9366(3) 0.14102(16) 0.0373(9) Uani 1 1 d . . .
H14A H 0.8810 0.9559 0.1430 0.045 Uiso 1 1 calc R . .
C15 C 0.6562(4) 1.0112(3) 0.11872(17) 0.0389(9) Uani 1 1 d . . .
H15A H 0.7206 1.0808 0.1049 0.047 Uiso 1 1 calc R . .
C16 C 0.4666(4) 0.9874(2) 0.11589(16) 0.0344(8) Uani 1 1 d . . .
C17 C 0.3769(4) 0.8838(2) 0.13601(15) 0.0337(8) Uani 1 1 d . . .
H17A H 0.2477 0.8649 0.1344 0.040 Uiso 1 1 calc R . .
C18 C 0.4724(4) 0.8082(2) 0.15826(15) 0.0316(8) Uani 1 1 d . . .
H18A H 0.4078 0.7384 0.1719 0.038 Uiso 1 1 calc R . .
C19 C 0.3634(4) 1.0702(3) 0.09255(17) 0.0438(9) Uani 1 1 d . . .
H19A H 0.3971 1.0958 0.0434 0.066 Uiso 1 1 calc R . .
H19B H 0.3937 1.1331 0.1313 0.066 Uiso 1 1 calc R . .
H19C H 0.2321 1.0357 0.0877 0.066 Uiso 1 1 calc R . .
O2 O 0.3108(3) 0.24742(17) 0.28410(11) 0.0380(6) Uani 1 1 d . . .
N5 N 0.3566(3) 0.0047(2) 0.59148(13) 0.0367(7) Uani 1 1 d . . .
N6 N 0.2724(3) -0.04456(19) 0.52123(13) 0.0332(7) Uani 1 1 d . . .
N7 N 0.1151(3) -0.03422(19) 0.41034(13) 0.0352(7) Uani 1 1 d . . .
N8 N 0.3964(3) 0.0923(2) 0.31241(13) 0.0334(7) Uani 1 1 d . . .
H8 H 0.478(4) 0.063(3) 0.3411(17) 0.040 Uiso 1 1 d . . .
C20 C 0.1971(4) -0.1604(2) 0.49439(16) 0.0360(8) Uani 1 1 d . . .
H20A H 0.1003 -0.1966 0.5247 0.043 Uiso 1 1 calc R . .
H20B H 0.2930 -0.2014 0.4957 0.043 Uiso 1 1 calc R . .
C21 C 0.1189(4) -0.1510(2) 0.41159(16) 0.0357(8) Uani 1 1 d . . .
H21A H 0.1982 -0.1703 0.3747 0.043 Uiso 1 1 calc R . .
H21B H -0.0054 -0.2002 0.3991 0.043 Uiso 1 1 calc R . .
C22 C 0.2232(4) 0.0229(2) 0.47284(15) 0.0305(8) Uani 1 1 d . . .
C23 C 0.2879(4) 0.1303(2) 0.50900(15) 0.0305(8) Uani 1 1 d . . .
C24 C 0.2913(4) 0.2388(2) 0.48994(16) 0.0335(8) Uani 1 1 d . . .
H24A H 0.2417 0.2518 0.4409 0.040 Uiso 1 1 calc R . .
C25 C 0.3676(4) 0.3240(3) 0.54395(17) 0.0378(8) Uani 1 1 d . . .
H25A H 0.3726 0.3973 0.5317 0.045 Uiso 1 1 calc R . .
C26 C 0.4396(4) 0.3067(3) 0.61756(17) 0.0400(9) Uani 1 1 d . . .
H26A H 0.4875 0.3682 0.6542 0.048 Uiso 1 1 calc R . .
C27 C 0.4418(4) 0.2028(3) 0.63739(16) 0.0379(9) Uani 1 1 d . . .
H27A H 0.4933 0.1921 0.6867 0.045 Uiso 1 1 calc R . .
C28 C 0.3659(4) 0.1127(2) 0.58295(16) 0.0324(8) Uani 1 1 d . . .
C29 C 0.0752(4) 0.0133(2) 0.33960(15) 0.0324(8) Uani 1 1 d . . .
H29A H 0.0629 0.0889 0.3521 0.039 Uiso 1 1 calc R . .
H29B H -0.0438 -0.0309 0.3136 0.039 Uiso 1 1 calc R . .
C30 C 0.2180(4) 0.0189(2) 0.28455(15) 0.0335(8) Uani 1 1 d . . .
H30A H 0.2332 -0.0564 0.2733 0.040 Uiso 1 1 calc R . .
H30B H 0.1723 0.0438 0.2360 0.040 Uiso 1 1 calc R . .
C31 C 0.4287(4) 0.2014(3) 0.30824(15) 0.0325(8) Uani 1 1 d . . .
C32 C 0.6210(4) 0.2680(2) 0.33173(15) 0.0304(8) Uani 1 1 d . . .
C33 C 0.6517(4) 0.3699(3) 0.37279(16) 0.0353(8) Uani 1 1 d . . .
H33A H 0.5520 0.3945 0.3890 0.042 Uiso 1 1 calc R . .
C34 C 0.8284(4) 0.4358(3) 0.39014(17) 0.0375(9) Uani 1 1 d . . .
H34A H 0.8488 0.5044 0.4198 0.045 Uiso 1 1 calc R . .
C35 C 0.9760(4) 0.4033(3) 0.36487(16) 0.0346(9) Uani 1 1 d . . .
C36 C 0.9441(4) 0.3016(3) 0.32418(16) 0.0356(8) Uani 1 1 d . . .
H36A H 1.0434 0.2778 0.3067 0.043 Uiso 1 1 calc R . .
C37 C 0.7678(4) 0.2336(3) 0.30842(16) 0.0349(8) Uani 1 1 d . . .
H37A H 0.7483 0.1631 0.2815 0.042 Uiso 1 1 calc R . .
C38 C 1.1650(4) 0.4796(3) 0.37904(18) 0.0445(9) Uani 1 1 d . . .
H38A H 1.1965 0.5015 0.4338 0.067 Uiso 1 1 calc R . .
H38B H 1.1683 0.5455 0.3514 0.067 Uiso 1 1 calc R . .
H38C H 1.2531 0.4416 0.3610 0.067 Uiso 1 1 calc R . .
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
_geom_angle_publ_flag
C9 N1 N2 100.8(2) . . ?
C3 N2 N1 116.1(2) . . ?
C3 N2 C1 112.8(2) . . ?
N1 N2 C1 130.8(2) . . ?
C3 N3 C10 126.1(2) . . ?
C3 N3 C2 108.2(2) . . ?
C10 N3 C2 122.8(2) . . ?
C12 N4 C11 121.2(2) . . ?
N2 C1 C2 100.8(2) . . ?
N3 C2 C1 104.7(2) . . ?
N2 C3 N3 111.8(2) . . ?
N2 C3 C4 106.5(2) . . ?
N3 C3 C4 141.5(3) . . ?
C5 C4 C3 135.7(3) . . ?
C5 C4 C9 121.2(2) . . ?
C3 C4 C9 103.0(2) . . ?
C6 C5 C4 117.9(3) . . ?
C5 C6 C7 121.2(3) . . ?
C8 C7 C6 122.3(3) . . ?
C7 C8 C9 117.8(3) . . ?
N1 C9 C8 127.0(3) . . ?
N1 C9 C4 113.5(2) . . ?
C8 C9 C4 119.5(2) . . ?
N3 C10 C11 114.4(2) . . ?
N4 C11 C10 114.5(2) . . ?
O1 C12 N4 121.7(3) . . ?
O1 C12 C13 121.5(3) . . ?
N4 C12 C13 116.7(2) . . ?
C18 C13 C14 117.6(3) . . ?
C18 C13 C12 123.1(2) . . ?
C14 C13 C12 119.1(3) . . ?
C15 C14 C13 120.9(3) . . ?
C14 C15 C16 121.7(3) . . ?
C15 C16 C17 117.4(3) . . ?
C15 C16 C19 121.3(3) . . ?
C17 C16 C19 121.3(3) . . ?
C18 C17 C16 121.2(3) . . ?
C17 C18 C13 121.2(3) . . ?
C28 N5 N6 101.7(2) . . ?
C22 N6 N5 115.5(2) . . ?
C22 N6 C20 112.5(2) . . ?
N5 N6 C20 131.0(2) . . ?
C22 N7 C29 124.6(2) . . ?
C22 N7 C21 108.1(2) . . ?
C29 N7 C21 121.8(2) . . ?
C31 N8 C30 121.0(3) . . ?
N6 C20 C21 101.1(2) . . ?
N7 C21 C20 104.2(2) . . ?
N6 C22 N7 111.4(3) . . ?
N6 C22 C23 106.6(2) . . ?
N7 C22 C23 141.6(3) . . ?
C22 C23 C24 136.7(3) . . ?
C22 C23 C28 103.3(2) . . ?
C24 C23 C28 120.0(3) . . ?
C25 C24 C23 118.1(3) . . ?
C24 C25 C26 122.0(3) . . ?
C27 C26 C25 121.3(3) . . ?
C26 C27 C28 118.4(3) . . ?
N5 C28 C27 127.1(3) . . ?
N5 C28 C23 112.8(3) . . ?
C27 C28 C23 120.1(3) . . ?
N7 C29 C30 114.6(2) . . ?
N8 C30 C29 114.5(2) . . ?
O2 C31 N8 123.3(2) . . ?
O2 C31 C32 119.9(3) . . ?
N8 C31 C32 116.7(3) . . ?
C37 C32 C33 119.2(3) . . ?
C37 C32 C31 121.2(3) . . ?
C33 C32 C31 119.4(3) . . ?
C32 C33 C34 119.9(3) . . ?
C33 C34 C35 121.1(3) . . ?
C36 C35 C34 118.5(3) . . ?
C36 C35 C38 121.1(3) . . ?
C34 C35 C38 120.4(3) . . ?
C35 C36 C37 120.7(3) . . ?
C32 C37 C36 120.4(3) . . ?
N2 C1 H1A 111.6 . . ?
C2 C1 H1A 111.6 . . ?
N2 C1 H1B 111.6 . . ?
C2 C1 H1B 111.6 . . ?
H1A C1 H1B 109.4 . . ?
N3 C2 H2A 110.8 . . ?
C1 C2 H2A 110.8 . . ?
N3 C2 H2B 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C6 C5 H5A 121.0 . . ?
C4 C5 H5A 121.0 . . ?
C5 C6 H6A 119.4 . . ?
C7 C6 H6A 119.4 . . ?
C8 C7 H7A 118.8 . . ?
C6 C7 H7A 118.8 . . ?
C7 C8 H8A 121.1 . . ?
C9 C8 H8A 121.1 . . ?
N3 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
N3 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
N4 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
N4 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C15 C14 H14A 119.5 . . ?
C13 C14 H14A 119.5 . . ?
C14 C15 H15A 119.2 . . ?
C16 C15 H15A 119.2 . . ?
C18 C17 H17A 119.4 . . ?
C16 C17 H17A 119.4 . . ?
C17 C18 H18A 119.4 . . ?
C13 C18 H18A 119.4 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C31 N8 H8 120.2(18) . . ?
C30 N8 H8 117.8(18) . . ?
N6 C20 H20A 111.6 . . ?
C21 C20 H20A 111.6 . . ?
N6 C20 H20B 111.6 . . ?
C21 C20 H20B 111.6 . . ?
H20A C20 H20B 109.4 . . ?
N7 C21 H21A 110.9 . . ?
C20 C21 H21A 110.9 . . ?
N7 C21 H21B 110.9 . . ?
C20 C21 H21B 110.9 . . ?
H21A C21 H21B 108.9 . . ?
C25 C24 H24A 120.9 . . ?
C23 C24 H24A 120.9 . . ?
C24 C25 H25A 119.0 . . ?
C26 C25 H25A 119.0 . . ?
C27 C26 H26A 119.3 . . ?
C25 C26 H26A 119.3 . . ?
C26 C27 H27A 120.8 . . ?
C28 C27 H27A 120.8 . . ?
N7 C29 H29A 108.6 . . ?
C30 C29 H29A 108.6 . . ?
N7 C29 H29B 108.6 . . ?
C30 C29 H29B 108.6 . . ?
H29A C29 H29B 107.6 . . ?
N8 C30 H30A 108.6 . . ?
C29 C30 H30A 108.6 . . ?
N8 C30 H30B 108.6 . . ?
C29 C30 H30B 108.6 . . ?
H30A C30 H30B 107.6 . . ?
C32 C33 H33A 120.0 . . ?
C34 C33 H33A 120.0 . . ?
C33 C34 H34A 119.4 . . ?
C35 C34 H34A 119.4 . . ?
C35 C36 H36A 119.6 . . ?
C37 C36 H36A 119.6 . . ?
C32 C37 H37A 119.8 . . ?
C36 C37 H37A 119.8 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 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 C12 1.237(3) . ?
N1 C9 1.358(3) . ?
N1 N2 1.378(3) . ?
N2 C3 1.322(3) . ?
N2 C1 1.464(3) . ?
N3 C3 1.355(3) . ?
N3 C10 1.442(3) . ?
N3 C2 1.473(3) . ?
N4 C12 1.358(4) . ?
N4 C11 1.446(4) . ?
C1 C2 1.551(4) . ?
C3 C4 1.407(3) . ?
C4 C5 1.406(4) . ?
C4 C9 1.428(4) . ?
C5 C6 1.376(4) . ?
C6 C7 1.413(4) . ?
C7 C8 1.371(4) . ?
C8 C9 1.423(3) . ?
C10 C11 1.520(5) . ?
C12 C13 1.488(4) . ?
C13 C18 1.392(4) . ?
C13 C14 1.404(4) . ?
C14 C15 1.372(4) . ?
C15 C16 1.395(4) . ?
C16 C17 1.396(4) . ?
C16 C19 1.501(5) . ?
C17 C18 1.382(4) . ?
O2 C31 1.236(4) . ?
N5 C28 1.358(4) . ?
N5 N6 1.375(3) . ?
N6 C22 1.328(3) . ?
N6 C20 1.456(4) . ?
N7 C22 1.358(3) . ?
N7 C29 1.453(3) . ?
N7 C21 1.473(4) . ?
N8 C31 1.338(4) . ?
N8 C30 1.460(3) . ?
C20 C21 1.546(4) . ?
C22 C23 1.405(4) . ?
C23 C24 1.417(4) . ?
C23 C28 1.432(3) . ?
C24 C25 1.361(4) . ?
C25 C26 1.410(4) . ?
C26 C27 1.373(4) . ?
C27 C28 1.406(4) . ?
C29 C30 1.521(4) . ?
C31 C32 1.500(4) . ?
C32 C37 1.383(4) . ?
C32 C33 1.387(4) . ?
C33 C34 1.389(4) . ?
C34 C35 1.390(5) . ?
C35 C36 1.381(4) . ?
C35 C38 1.508(4) . ?
C36 C37 1.393(4) . ?
N4 H4 0.89(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
N8 H8 0.92(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9500 . ?
C27 H27A 0.9500 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C33 H33A 0.9500 . ?
C34 H34A 0.9500 . ?
C36 H36A 0.9500 . ?
C37 H37A 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
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
N4 H4 N1 0.89(3) 2.08(3) 2.961(3) 167(3) 2_665
N8 H8 N5 0.92(3) 2.02(3) 2.938(3) 176(3) 2_656
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
C9 N1 N2 C3 -2.4(4) . . . . ?
C9 N1 N2 C1 -176.0(3) . . . . ?
C3 N2 C1 C2 6.6(3) . . . . ?
N1 N2 C1 C2 -179.6(3) . . . . ?
C3 N3 C2 C1 12.6(3) . . . . ?
C10 N3 C2 C1 174.6(3) . . . . ?
N2 C1 C2 N3 -11.1(3) . . . . ?
N1 N2 C3 N3 -173.6(3) . . . . ?
C1 N2 C3 N3 1.2(4) . . . . ?
N1 N2 C3 C4 2.8(4) . . . . ?
C1 N2 C3 C4 177.6(3) . . . . ?
C10 N3 C3 N2 -170.2(3) . . . . ?
C2 N3 C3 N2 -9.0(4) . . . . ?
C10 N3 C3 C4 15.3(7) . . . . ?
C2 N3 C3 C4 176.5(4) . . . . ?
N2 C3 C4 C5 175.4(4) . . . . ?
N3 C3 C4 C5 -10.0(8) . . . . ?
N2 C3 C4 C9 -1.8(3) . . . . ?
N3 C3 C4 C9 172.8(4) . . . . ?
C3 C4 C5 C6 -177.1(4) . . . . ?
C9 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C7 -1.3(5) . . . . ?
C5 C6 C7 C8 1.3(5) . . . . ?
C6 C7 C8 C9 0.3(5) . . . . ?
N2 N1 C9 C8 -178.0(3) . . . . ?
N2 N1 C9 C4 1.0(3) . . . . ?
C7 C8 C9 N1 177.2(3) . . . . ?
C7 C8 C9 C4 -1.8(5) . . . . ?
C5 C4 C9 N1 -177.3(3) . . . . ?
C3 C4 C9 N1 0.4(4) . . . . ?
C5 C4 C9 C8 1.9(5) . . . . ?
C3 C4 C9 C8 179.6(3) . . . . ?
C3 N3 C10 C11 89.7(4) . . . . ?
C2 N3 C10 C11 -69.0(4) . . . . ?
C12 N4 C11 C10 -84.3(3) . . . . ?
N3 C10 C11 N4 -62.0(3) . . . . ?
C11 N4 C12 O1 8.0(5) . . . . ?
C11 N4 C12 C13 -170.0(3) . . . . ?
O1 C12 C13 C18 -154.9(3) . . . . ?
N4 C12 C13 C18 23.1(4) . . . . ?
O1 C12 C13 C14 19.8(4) . . . . ?
N4 C12 C13 C14 -162.3(3) . . . . ?
C18 C13 C14 C15 -0.8(4) . . . . ?
C12 C13 C14 C15 -175.7(3) . . . . ?
C13 C14 C15 C16 0.9(5) . . . . ?
C14 C15 C16 C17 -0.6(5) . . . . ?
C14 C15 C16 C19 179.1(3) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C19 C16 C17 C18 -179.3(3) . . . . ?
C16 C17 C18 C13 -0.4(4) . . . . ?
C14 C13 C18 C17 0.6(4) . . . . ?
C12 C13 C18 C17 175.3(3) . . . . ?
C28 N5 N6 C22 -2.9(3) . . . . ?
C28 N5 N6 C20 -170.2(3) . . . . ?
C22 N6 C20 C21 10.0(3) . . . . ?
N5 N6 C20 C21 177.6(3) . . . . ?
C22 N7 C21 C20 16.1(3) . . . . ?
C29 N7 C21 C20 170.8(2) . . . . ?
N6 C20 C21 N7 -15.1(3) . . . . ?
N5 N6 C22 N7 -169.8(2) . . . . ?
C20 N6 C22 N7 -0.2(4) . . . . ?
N5 N6 C22 C23 4.2(3) . . . . ?
C20 N6 C22 C23 173.9(2) . . . . ?
C29 N7 C22 N6 -164.4(3) . . . . ?
C21 N7 C22 N6 -10.5(3) . . . . ?
C29 N7 C22 C23 24.8(6) . . . . ?
C21 N7 C22 C23 178.7(4) . . . . ?
N6 C22 C23 C24 176.6(3) . . . . ?
N7 C22 C23 C24 -12.3(7) . . . . ?
N6 C22 C23 C28 -3.5(3) . . . . ?
N7 C22 C23 C28 167.5(4) . . . . ?
C22 C23 C24 C25 178.9(3) . . . . ?
C28 C23 C24 C25 -0.9(4) . . . . ?
C23 C24 C25 C26 -1.0(4) . . . . ?
C24 C25 C26 C27 2.4(5) . . . . ?
C25 C26 C27 C28 -1.6(4) . . . . ?
N6 N5 C28 C27 -179.4(3) . . . . ?
N6 N5 C28 C23 0.4(3) . . . . ?
C26 C27 C28 N5 179.4(3) . . . . ?
C26 C27 C28 C23 -0.3(4) . . . . ?
C22 C23 C28 N5 2.0(3) . . . . ?
C24 C23 C28 N5 -178.1(3) . . . . ?
C22 C23 C28 C27 -178.3(3) . . . . ?
C24 C23 C28 C27 1.6(4) . . . . ?
C22 N7 C29 C30 84.5(4) . . . . ?
C21 N7 C29 C30 -66.0(3) . . . . ?
C31 N8 C30 C29 -80.6(3) . . . . ?
N7 C29 C30 N8 -65.0(3) . . . . ?
C30 N8 C31 O2 3.1(4) . . . . ?
C30 N8 C31 C32 -174.5(2) . . . . ?
O2 C31 C32 C37 -133.6(3) . . . . ?
N8 C31 C32 C37 44.1(3) . . . . ?
O2 C31 C32 C33 41.5(4) . . . . ?
N8 C31 C32 C33 -140.8(3) . . . . ?
C37 C32 C33 C34 -0.1(4) . . . . ?
C31 C32 C33 C34 -175.4(2) . . . . ?
C32 C33 C34 C35 2.1(4) . . . . ?
C33 C34 C35 C36 -2.3(4) . . . . ?
C33 C34 C35 C38 175.3(2) . . . . ?
C34 C35 C36 C37 0.4(4) . . . . ?
C38 C35 C36 C37 -177.1(2) . . . . ?
C33 C32 C37 C36 -1.7(4) . . . . ?
C31 C32 C37 C36 173.4(2) . . . . ?
C35 C36 C37 C32 1.6(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139091385
