#------------------------------------------------------------------------------
#$Date: 2020-06-03 05:53:35 +0300 (Wed, 03 Jun 2020) $
#$Revision: 252561 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240592.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_7240592
loop_
_publ_author_name
'Poirier, Marion'
'Pujol-Giménez, Jonai'
'Manatschal, Cristina'
'Bühlmann, Sven'
'Embaby, Ahmed'
'Javor, Sacha'
'Hediger, Matthias A.'
'Reymond, Jean-Louis'
_publ_section_title
;
 Pyrazolyl-pyrimidones inhibit the function of human solute carrier
 protein SLC11A2 (hDMT1) by metal chelation
;
_journal_name_full               'RSC Medicinal Chemistry'
_journal_paper_doi               10.1039/D0MD00085J
_journal_year                    2020
_chemical_formula_moiety         'C13 H16 N4 O'
_chemical_formula_sum            'C13 H16 N4 O'
_chemical_formula_weight         244.3
_chemical_name_systematic
6-methyl-2-(3-methyl-4,5,6,7-tetrahydro-2H-indazol-2-yl)pyrimidin-4(3H)-one
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-09-06T14:31:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-01-10 deposited with the CCDC.	2020-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                93.396(3)
_cell_angle_beta                 99.154(3)
_cell_angle_gamma                117.195(4)
_cell_formula_units_Z            4
_cell_length_a                   8.1640(3)
_cell_length_b                   8.5511(4)
_cell_length_c                   19.8770(7)
_cell_measurement_reflns_used    4470
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.441
_cell_measurement_theta_min      2.085
_cell_volume                     1204.69(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0965
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.013067
_diffrn_orient_matrix_UB_12      -0.0014783
_diffrn_orient_matrix_UB_13      0.0360541
_diffrn_orient_matrix_UB_21      0.0711968
_diffrn_orient_matrix_UB_22      -0.0250241
_diffrn_orient_matrix_UB_23      -0.0015312
_diffrn_orient_matrix_UB_31      0.0688495
_diffrn_orient_matrix_UB_32      0.0909367
_diffrn_orient_matrix_UB_33      0.0058633
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16639
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.259
_diffrn_reflns_theta_min         2.099
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.76978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.373
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         5444
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0482P)²+0.4126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1186
_reflns_Friedel_coverage         0
_reflns_number_gt                3996
_reflns_number_total             5444
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0md00085j3.cif
_cod_data_source_block           16jlr002
_cod_original_cell_volume        1204.68(9)
_cod_database_code               7240592
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_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 0.6757(2) 0.4829(2) 0.92751(8) 0.0228(3) Uani 1 1 d . . . . .
C2 C 0.5723(2) 0.4948(2) 0.80783(8) 0.0315(4) Uani 1 1 d . . . . .
C3 C 0.4106(2) 0.3305(2) 0.81040(8) 0.0287(4) Uani 1 1 d . . . . .
H3 H 0.3117 0.2736 0.7708 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3977(2) 0.2554(2) 0.86884(8) 0.0243(3) Uani 1 1 d . . . . .
C5 C 0.2386(2) 0.0774(2) 0.87219(9) 0.0314(4) Uani 1 1 d . . . . .
H5A H 0.1453 0.0354 0.8287 0.047 Uiso 1 1 calc R U . . .
H5B H 0.1795 0.0877 0.9103 0.047 Uiso 1 1 calc R U . . .
H5C H 0.287 -0.0074 0.8798 0.047 Uiso 1 1 calc R U . . .
C6 C 0.8304(2) 0.5347(2) 1.05266(8) 0.0228(3) Uani 1 1 d . . . . .
C7 C 0.6930(2) 0.3715(2) 1.07534(8) 0.0289(4) Uani 1 1 d . . . . .
H7A H 0.5667 0.3605 1.0631 0.043 Uiso 1 1 calc R U . . .
H7B H 0.7283 0.3795 1.1254 0.043 Uiso 1 1 calc R U . . .
H7C H 0.6934 0.2671 1.0524 0.043 Uiso 1 1 calc R U . . .
C8 C 0.9917(2) 0.6745(2) 1.09059(8) 0.0235(3) Uani 1 1 d . . . . .
C9 C 1.0739(2) 0.7108(2) 1.16636(8) 0.0288(4) Uani 1 1 d . U . . .
H9A1 H 1.0832 0.6057 1.1806 0.035 Uiso 0.855(9) 1 calc R U P A 1
H9A2 H 0.9892 0.7309 1.1921 0.035 Uiso 0.855(9) 1 calc R U P A 1
H9B1 H 1.1417 0.6419 1.1779 0.035 Uiso 0.145(9) 1 calc R U P A 2
H9B2 H 0.9741 0.6794 1.1933 0.035 Uiso 0.145(9) 1 calc R U P A 2
C10A C 1.2680(3) 0.8724(4) 1.18436(11) 0.0285(6) Uani 0.855(9) 1 d . U P A 1
H10A H 1.3625 0.8369 1.1747 0.034 Uiso 0.855(9) 1 calc R U P A 1
H10B H 1.2991 0.9167 1.2343 0.034 Uiso 0.855(9) 1 calc R U P A 1
C11A C 1.2801(4) 1.0229(3) 1.14371(12) 0.0292(7) Uani 0.855(9) 1 d . U P A 1
H11A H 1.4063 1.1273 1.1595 0.035 Uiso 0.855(9) 1 calc R U P A 1
H11B H 1.1856 1.0585 1.1534 0.035 Uiso 0.855(9) 1 calc R U P A 1
C10B C 1.222(3) 0.928(2) 1.1824(8) 0.036(4) Uani 0.145(9) 1 d . U P A 2
H10C H 1.1472 0.9927 1.1812 0.043 Uiso 0.145(9) 1 calc R U P A 2
H10D H 1.2985 0.9568 1.2297 0.043 Uiso 0.145(9) 1 calc R U P A 2
C11B C 1.350(3) 0.994(2) 1.1339(8) 0.040(4) Uani 0.145(9) 1 d . U P A 2
H11C H 1.4384 1.1219 1.149 0.048 Uiso 0.145(9) 1 calc R U P A 2
H11D H 1.4245 0.9294 1.1343 0.048 Uiso 0.145(9) 1 calc R U P A 2
C12 C 1.2455(2) 0.9682(2) 1.06541(9) 0.0307(4) Uani 1 1 d . U . . .
H12A H 1.2324 1.0601 1.0405 0.037 Uiso 0.855(9) 1 calc R U P A 1
H12B H 1.3533 0.9563 1.0539 0.037 Uiso 0.855(9) 1 calc R U P A 1
H12C H 1.3281 0.9781 1.0326 0.037 Uiso 0.145(9) 1 calc R U P A 2
H12D H 1.2122 1.0655 1.0614 0.037 Uiso 0.145(9) 1 calc R U P A 2
C13 C 1.0689(2) 0.7943(2) 1.04435(8) 0.0241(3) Uani 1 1 d . . . . .
C14 C -0.2320(2) -0.0139(2) 0.52784(8) 0.0226(3) Uani 1 1 d . . . . .
C15 C -0.1091(2) 0.0137(2) 0.64922(8) 0.0278(4) Uani 1 1 d . . . . .
C16 C -0.2772(2) -0.1504(2) 0.64624(8) 0.0283(4) Uani 1 1 d . . . . .
H16 H -0.3 -0.2023 0.687 0.034 Uiso 1 1 calc R U . . .
C17 C -0.4042(2) -0.2324(2) 0.58586(8) 0.0254(3) Uani 1 1 d . . . . .
C18 C -0.5767(2) -0.4070(2) 0.58057(9) 0.0304(4) Uani 1 1 d . . . . .
H18A H -0.583 -0.4435 0.6263 0.046 Uiso 1 1 calc R U . . .
H18B H -0.5714 -0.4968 0.5493 0.046 Uiso 1 1 calc R U . . .
H18C H -0.6887 -0.395 0.5626 0.046 Uiso 1 1 calc R U . . .
C19 C -0.3015(2) 0.0160(2) 0.40239(8) 0.0238(3) Uani 1 1 d . . . . .
C20 C -0.4771(2) -0.1547(2) 0.37671(9) 0.0325(4) Uani 1 1 d . . . . .
H20A H -0.4517 -0.2543 0.3848 0.049 Uiso 1 1 calc R U . . .
H20B H -0.5209 -0.162 0.3272 0.049 Uiso 1 1 calc R U . . .
H20C H -0.5743 -0.1604 0.4012 0.049 Uiso 1 1 calc R U . . .
C21 C -0.2075(2) 0.1505(2) 0.36725(8) 0.0241(3) Uani 1 1 d . . . . .
C22 C -0.0484(2) 0.2811(2) 0.41555(8) 0.0243(3) Uani 1 1 d . . . . .
C23 C 0.0928(2) 0.4534(2) 0.39833(8) 0.0292(4) Uani 1 1 d . . . . .
H23A H 0.2124 0.4503 0.398 0.035 Uiso 1 1 calc R U . . .
H23B H 0.1186 0.5526 0.4338 0.035 Uiso 1 1 calc R U . . .
C24 C 0.0163(3) 0.4835(2) 0.32746(9) 0.0416(5) Uani 1 1 d . . . . .
H24A H -0.0768 0.5252 0.332 0.05 Uiso 1 1 calc R U . . .
H24B H 0.1211 0.5779 0.311 0.05 Uiso 1 1 calc R U . . .
C25 C -0.0758(3) 0.3170(2) 0.27469(9) 0.0431(5) Uani 1 1 d . . . . .
H25A H 0.0156 0.2724 0.2714 0.052 Uiso 1 1 calc R U . . .
H25B H -0.1111 0.3464 0.229 0.052 Uiso 1 1 calc R U . . .
C26 C -0.2513(2) 0.1713(2) 0.29333(8) 0.0309(4) Uani 1 1 d . . . . .
H26A H -0.3546 0.203 0.2858 0.037 Uiso 1 1 calc R U . . .
H26B H -0.2932 0.0575 0.2634 0.037 Uiso 1 1 calc R U . . .
N1 N 0.7029(2) 0.56375(18) 0.87076(7) 0.0281(3) Uani 1 1 d . . . . .
N2 N 0.53135(18) 0.33271(17) 0.92983(7) 0.0244(3) Uani 1 1 d . . . . .
N3 N 0.81685(18) 0.57469(16) 0.98619(6) 0.0237(3) Uani 1 1 d . . . . .
N4 N 0.96496(18) 0.73677(16) 0.98103(7) 0.0267(3) Uani 1 1 d . . . . .
N5 N -0.0978(2) 0.07478(18) 0.58569(7) 0.0262(3) Uani 1 1 d . . . . .
N6 N -0.38353(19) -0.16346(17) 0.52460(6) 0.0258(3) Uani 1 1 d . . . . .
N7 N -0.19726(18) 0.06851(16) 0.46953(6) 0.0245(3) Uani 1 1 d . . . . .
N8 N -0.03997(18) 0.23335(17) 0.47753(7) 0.0262(3) Uani 1 1 d . . . . .
O1 O 0.6052(2) 0.57490(17) 0.75852(6) 0.0488(4) Uani 1 1 d . . . . .
O2 O 0.01783(17) 0.09905(16) 0.69967(6) 0.0377(3) Uani 1 1 d . . . . .
H1 H 0.807(3) 0.665(3) 0.8742(10) 0.045 Uiso 1 1 d . U . . .
H5 H 0.002(3) 0.177(3) 0.5823(10) 0.045 Uiso 1 1 d . 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 0 '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 0.006 '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
N2 C1 N1 124.74(14) . . ?
N2 C1 N3 120.47(14) . . ?
N1 C1 N3 114.79(14) . . ?
O1 C2 N1 119.58(16) . . ?
O1 C2 C3 127.72(16) . . ?
N1 C2 C3 112.69(14) . . ?
C4 C3 C2 120.62(15) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 N2 123.59(15) . . ?
C3 C4 C5 122.34(15) . . ?
N2 C4 C5 114.05(14) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C8 C6 N3 105.60(13) . . ?
C8 C6 C7 129.09(14) . . ?
N3 C6 C7 125.31(14) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 C13 106.14(14) . . ?
C6 C8 C9 130.07(14) . . ?
C13 C8 C9 123.67(14) . . ?
C8 C9 C10A 111.49(15) . . ?
C8 C9 C10B 104.7(5) . . ?
C8 C9 H9A1 109.3 . . ?
C10A C9 H9A1 109.3 . . ?
C8 C9 H9A2 109.3 . . ?
C10A C9 H9A2 109.3 . . ?
H9A1 C9 H9A2 108 . . ?
C8 C9 H9B1 110.8 . . ?
C10B C9 H9B1 110.8 . . ?
C8 C9 H9B2 110.8 . . ?
C10B C9 H9B2 110.8 . . ?
H9B1 C9 H9B2 108.9 . . ?
C9 C10A C11A 112.4(2) . . ?
C9 C10A H10A 109.1 . . ?
C11A C10A H10A 109.1 . . ?
C9 C10A H10B 109.1 . . ?
C11A C10A H10B 109.1 . . ?
H10A C10A H10B 107.8 . . ?
C10A C11A C12 112.4(2) . . ?
C10A C11A H11A 109.1 . . ?
C12 C11A H11A 109.1 . . ?
C10A C11A H11B 109.1 . . ?
C12 C11A H11B 109.1 . . ?
H11A C11A H11B 107.9 . . ?
C11B C10B C9 114.7(17) . . ?
C11B C10B H10C 108.6 . . ?
C9 C10B H10C 108.6 . . ?
C11B C10B H10D 108.6 . . ?
C9 C10B H10D 108.6 . . ?
H10C C10B H10D 107.6 . . ?
C12 C11B C10B 110.7(18) . . ?
C12 C11B H11C 109.5 . . ?
C10B C11B H11C 109.5 . . ?
C12 C11B H11D 109.5 . . ?
C10B C11B H11D 109.5 . . ?
H11C C11B H11D 108.1 . . ?
C11B C12 C13 115.0(6) . . ?
C13 C12 C11A 108.44(15) . . ?
C13 C12 H12A 110 . . ?
C11A C12 H12A 110 . . ?
C13 C12 H12B 110 . . ?
C11A C12 H12B 110 . . ?
H12A C12 H12B 108.4 . . ?
C11B C12 H12C 108.5 . . ?
C13 C12 H12C 108.5 . . ?
C11B C12 H12D 108.5 . . ?
C13 C12 H12D 108.5 . . ?
H12C C12 H12D 107.5 . . ?
N4 C13 C8 112.27(14) . . ?
N4 C13 C12 124.19(14) . . ?
C8 C13 C12 123.52(14) . . ?
N6 C14 N5 124.74(14) . . ?
N6 C14 N7 120.69(14) . . ?
N5 C14 N7 114.57(14) . . ?
O2 C15 N5 119.80(15) . . ?
O2 C15 C16 127.40(15) . . ?
N5 C15 C16 112.80(14) . . ?
C17 C16 C15 120.82(15) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 N6 123.15(15) . . ?
C16 C17 C18 122.03(15) . . ?
N6 C17 C18 114.81(14) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C19 N7 105.59(13) . . ?
C21 C19 C20 129.12(14) . . ?
N7 C19 C20 125.29(14) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 C22 106.36(14) . . ?
C19 C21 C26 130.65(14) . . ?
C22 C21 C26 122.99(14) . . ?
N8 C22 C21 111.96(14) . . ?
N8 C22 C23 124.15(14) . . ?
C21 C22 C23 123.89(14) . . ?
C22 C23 C24 109.81(13) . . ?
C22 C23 H23A 109.7 . . ?
C24 C23 H23A 109.7 . . ?
C22 C23 H23B 109.7 . . ?
C24 C23 H23B 109.7 . . ?
H23A C23 H23B 108.2 . . ?
C25 C24 C23 112.53(15) . . ?
C25 C24 H24A 109.1 . . ?
C23 C24 H24A 109.1 . . ?
C25 C24 H24B 109.1 . . ?
C23 C24 H24B 109.1 . . ?
H24A C24 H24B 107.8 . . ?
C24 C25 C26 111.90(16) . . ?
C24 C25 H25A 109.2 . . ?
C26 C25 H25A 109.2 . . ?
C24 C25 H25B 109.2 . . ?
C26 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C21 C26 C25 109.59(14) . . ?
C21 C26 H26A 109.8 . . ?
C25 C26 H26A 109.8 . . ?
C21 C26 H26B 109.8 . . ?
C25 C26 H26B 109.8 . . ?
H26A C26 H26B 108.2 . . ?
C1 N1 C2 122.84(14) . . ?
C1 N1 H1 118.0(13) . . ?
C2 N1 H1 119.2(13) . . ?
C1 N2 C4 115.46(13) . . ?
C6 N3 N4 112.06(12) . . ?
C6 N3 C1 130.00(13) . . ?
N4 N3 C1 117.84(12) . . ?
C13 N4 N3 103.92(12) . . ?
C14 N5 C15 122.79(14) . . ?
C14 N5 H5 117.6(13) . . ?
C15 N5 H5 119.6(13) . . ?
C14 N6 C17 115.68(13) . . ?
N8 N7 C19 111.90(12) . . ?
N8 N7 C14 117.74(12) . . ?
C19 N7 C14 130.29(13) . . ?
C22 N8 N7 104.19(12) . . ?
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
C1 N2 1.2967(19) . ?
C1 N1 1.353(2) . ?
C1 N3 1.393(2) . ?
C2 O1 1.223(2) . ?
C2 N1 1.401(2) . ?
C2 C3 1.433(2) . ?
C3 C4 1.356(2) . ?
C3 H3 0.95 . ?
C4 N2 1.386(2) . ?
C4 C5 1.497(2) . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 C8 1.368(2) . ?
C6 N3 1.3846(19) . ?
C6 C7 1.487(2) . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 C13 1.413(2) . ?
C8 C9 1.499(2) . ?
C9 C10A 1.519(3) . ?
C9 C10B 1.663(16) . ?
C9 H9A1 0.99 . ?
C9 H9A2 0.99 . ?
C9 H9B1 0.99 . ?
C9 H9B2 0.99 . ?
C10A C11A 1.533(4) . ?
C10A H10A 0.99 . ?
C10A H10B 0.99 . ?
C11A C12 1.541(3) . ?
C11A H11A 0.99 . ?
C11A H11B 0.99 . ?
C10B C11B 1.48(3) . ?
C10B H10C 0.99 . ?
C10B H10D 0.99 . ?
C11B C12 1.433(15) . ?
C11B H11C 0.99 . ?
C11B H11D 0.99 . ?
C12 C13 1.497(2) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C12 H12C 0.99 . ?
C12 H12D 0.99 . ?
C13 N4 1.323(2) . ?
C14 N6 1.2994(19) . ?
C14 N5 1.354(2) . ?
C14 N7 1.3927(19) . ?
C15 O2 1.2262(19) . ?
C15 N5 1.395(2) . ?
C15 C16 1.435(2) . ?
C16 C17 1.359(2) . ?
C16 H16 0.95 . ?
C17 N6 1.3851(19) . ?
C17 C18 1.495(2) . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C19 C21 1.363(2) . ?
C19 N7 1.3874(19) . ?
C19 C20 1.488(2) . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C21 C22 1.416(2) . ?
C21 C26 1.497(2) . ?
C22 N8 1.322(2) . ?
C22 C23 1.500(2) . ?
C23 C24 1.533(2) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C24 C25 1.512(3) . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
C25 C26 1.528(2) . ?
C25 H25A 0.99 . ?
C25 H25B 0.99 . ?
C26 H26A 0.99 . ?
C26 H26B 0.99 . ?
N1 H1 0.88(2) . ?
N3 N4 1.3850(17) . ?
N5 H5 0.89(2) . ?
N7 N8 1.3839(17) . ?
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 C2 C3 C4 177.92(18) . . . . ?
N1 C2 C3 C4 -1.6(2) . . . . ?
C2 C3 C4 N2 2.9(3) . . . . ?
C2 C3 C4 C5 -175.26(15) . . . . ?
N3 C6 C8 C13 0.09(17) . . . . ?
C7 C6 C8 C13 -179.62(16) . . . . ?
N3 C6 C8 C9 176.22(15) . . . . ?
C7 C6 C8 C9 -3.5(3) . . . . ?
C6 C8 C9 C10A 173.3(2) . . . . ?
C13 C8 C9 C10A -11.2(3) . . . . ?
C6 C8 C9 C10B -160.3(9) . . . . ?
C13 C8 C9 C10B 15.3(9) . . . . ?
C8 C9 C10A C11A 39.8(3) . . . . ?
C9 C10A C11A C12 -62.4(4) . . . . ?
C8 C9 C10B C11B -48(2) . . . . ?
C9 C10B C11B C12 63(3) . . . . ?
C10B C11B C12 C13 -41(2) . . . . ?
C10A C11A C12 C13 49.9(3) . . . . ?
C6 C8 C13 N4 0.18(19) . . . . ?
C9 C8 C13 N4 -176.27(14) . . . . ?
C6 C8 C13 C12 178.75(15) . . . . ?
C9 C8 C13 C12 2.3(2) . . . . ?
C11B C12 C13 N4 -171.9(13) . . . . ?
C11A C12 C13 N4 157.1(2) . . . . ?
C11B C12 C13 C8 9.7(13) . . . . ?
C11A C12 C13 C8 -21.3(3) . . . . ?
O2 C15 C16 C17 -178.44(17) . . . . ?
N5 C15 C16 C17 1.3(2) . . . . ?
C15 C16 C17 N6 -1.5(2) . . . . ?
C15 C16 C17 C18 177.49(15) . . . . ?
N7 C19 C21 C22 -0.32(17) . . . . ?
C20 C19 C21 C22 -179.47(16) . . . . ?
N7 C19 C21 C26 -179.57(16) . . . . ?
C20 C19 C21 C26 1.3(3) . . . . ?
C19 C21 C22 N8 0.39(19) . . . . ?
C26 C21 C22 N8 179.71(15) . . . . ?
C19 C21 C22 C23 -179.33(15) . . . . ?
C26 C21 C22 C23 0.0(3) . . . . ?
N8 C22 C23 C24 -167.08(16) . . . . ?
C21 C22 C23 C24 12.6(2) . . . . ?
C22 C23 C24 C25 -43.5(2) . . . . ?
C23 C24 C25 C26 64.5(2) . . . . ?
C19 C21 C26 C25 -163.48(17) . . . . ?
C22 C21 C26 C25 17.4(2) . . . . ?
C24 C25 C26 C21 -48.1(2) . . . . ?
N2 C1 N1 C2 2.1(3) . . . . ?
N3 C1 N1 C2 -177.38(14) . . . . ?
O1 C2 N1 C1 179.72(16) . . . . ?
C3 C2 N1 C1 -0.7(2) . . . . ?
N1 C1 N2 C4 -0.9(2) . . . . ?
N3 C1 N2 C4 178.54(13) . . . . ?
C3 C4 N2 C1 -1.6(2) . . . . ?
C5 C4 N2 C1 176.68(14) . . . . ?
C8 C6 N3 N4 -0.31(17) . . . . ?
C7 C6 N3 N4 179.40(14) . . . . ?
C8 C6 N3 C1 -176.48(15) . . . . ?
C7 C6 N3 C1 3.2(3) . . . . ?
N2 C1 N3 C6 -2.3(3) . . . . ?
N1 C1 N3 C6 177.22(14) . . . . ?
N2 C1 N3 N4 -178.26(13) . . . . ?
N1 C1 N3 N4 1.2(2) . . . . ?
C8 C13 N4 N3 -0.35(17) . . . . ?
C12 C13 N4 N3 -178.92(14) . . . . ?
C6 N3 N4 C13 0.41(17) . . . . ?
C1 N3 N4 C13 177.09(13) . . . . ?
N6 C14 N5 C15 -0.3(3) . . . . ?
N7 C14 N5 C15 179.35(14) . . . . ?
O2 C15 N5 C14 179.30(15) . . . . ?
C16 C15 N5 C14 -0.5(2) . . . . ?
N5 C14 N6 C17 0.2(2) . . . . ?
N7 C14 N6 C17 -179.42(13) . . . . ?
C16 C17 N6 C14 0.7(2) . . . . ?
C18 C17 N6 C14 -178.35(14) . . . . ?
C21 C19 N7 N8 0.17(17) . . . . ?
C20 C19 N7 N8 179.36(15) . . . . ?
C21 C19 N7 C14 176.97(15) . . . . ?
C20 C19 N7 C14 -3.8(3) . . . . ?
N6 C14 N7 N8 175.66(14) . . . . ?
N5 C14 N7 N8 -4.0(2) . . . . ?
N6 C14 N7 C19 -1.0(3) . . . . ?
N5 C14 N7 C19 179.37(15) . . . . ?
C21 C22 N8 N7 -0.28(18) . . . . ?
C23 C22 N8 N7 179.44(15) . . . . ?
C19 N7 N8 C22 0.07(17) . . . . ?
C14 N7 N8 C22 -177.18(13) . . . . ?
