#------------------------------------------------------------------------------
#$Date: 2025-08-23 01:35:05 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301870 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/12/7241239.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_7241239
loop_
_publ_author_name
'Said, Awad I.'
'Palkó, Márta'
'Haukka, Matti'
'Fülöp, Ferenc'
_publ_section_title
;
 Retro Diels Alder protocol for regioselective synthesis of novel
 [1,2,4]triazolo[4,3-a]pyrimidin-7(1H)-ones
;
_journal_issue                   56
_journal_name_full               'RSC Advances'
_journal_page_first              33937
_journal_page_last               33943
_journal_paper_doi               10.1039/D0RA04345A
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C19 H18 N4 O2, C2 H6 O'
_chemical_formula_sum            'C21 H24 N4 O3'
_chemical_formula_weight         380.44
_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   mixed
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2020-01-29 deposited with the CCDC.	2020-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                104.318(3)
_cell_angle_beta                 104.565(3)
_cell_angle_gamma                103.319(3)
_cell_formula_units_Z            4
_cell_length_a                   9.5893(2)
_cell_length_b                   14.2652(5)
_cell_length_c                   15.8257(5)
_cell_measurement_reflns_used    8785
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.0460
_cell_measurement_theta_min      2.2700
_cell_volume                     1928.87(12)
_computing_cell_refinement
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
;
_computing_data_collection
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
;
_computing_data_reduction
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
;
_computing_molecular_graphics
'CrystaMaker X (CrystalMaker Software ltd., 2019)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2017)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 16.0107
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            34591
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.628
_diffrn_reflns_theta_min         2.277
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.105
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     519
_refine_ls_number_reflns         10787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0492
_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)+(0.0618P)²+0.6436P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1363
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8088
_reflns_number_total             10787
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra04345a2.cif
_cod_data_source_block           7a_amis22
_cod_depositor_comments
'Adding full bibliography for 7241239--7241240.cif.'
_cod_original_cell_volume        1928.87(11)
_cod_database_code               7241239
_shelx_shelxl_version_number     2017/1
_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_min   0.973
_shelx_estimated_absorpt_t_max   0.991
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 0.47027(14) 0.63728(9) 0.72194(8) 0.0384(3) Uani 1 1 d . . . . .
O2 O 0.23784(12) 0.15221(8) 0.69199(7) 0.0293(2) Uani 1 1 d . . . . .
N1 N 0.57494(13) 0.45432(8) 0.90628(7) 0.0223(2) Uani 1 1 d . . . . .
N2 N 0.62722(13) 0.55170(9) 0.90396(8) 0.0246(2) Uani 1 1 d . . . . .
N3 N 0.43754(13) 0.45538(9) 0.77544(8) 0.0234(2) Uani 1 1 d . . . . .
N4 N 0.39738(13) 0.29451(9) 0.80559(8) 0.0244(2) Uani 1 1 d . . . . .
C1 C 0.90922(18) 0.31955(12) 1.17970(11) 0.0339(3) Uani 1 1 d . . . . .
H1A H 0.907418 0.250683 1.148103 0.051 Uiso 1 1 calc R U . . .
H1B H 0.863889 0.317856 1.228539 0.051 Uiso 1 1 calc R U . . .
H1C H 1.014327 0.364564 1.206890 0.051 Uiso 1 1 calc R U . . .
C2 C 0.82005(16) 0.35886(11) 1.11135(9) 0.0253(3) Uani 1 1 d . . . . .
C3 C 0.89017(16) 0.44243(11) 1.08971(9) 0.0270(3) Uani 1 1 d . . . . .
H3 H 0.995105 0.477528 1.120861 0.032 Uiso 1 1 calc R U . . .
C4 C 0.80907(16) 0.47529(10) 1.02326(9) 0.0256(3) Uani 1 1 d . . . . .
H4 H 0.858375 0.531821 1.008435 0.031 Uiso 1 1 calc R U . . .
C5 C 0.65559(15) 0.42480(10) 0.97882(9) 0.0215(3) Uani 1 1 d . . . . .
C6 C 0.58119(16) 0.34347(11) 1.00127(9) 0.0245(3) Uani 1 1 d . . . . .
H6 H 0.475172 0.310780 0.972315 0.029 Uiso 1 1 calc R U . . .
C7 C 0.66507(16) 0.31085(11) 1.06702(9) 0.0261(3) Uani 1 1 d . . . . .
H7 H 0.615455 0.254543 1.081994 0.031 Uiso 1 1 calc R U . . .
C8 C 0.54184(16) 0.54979(10) 0.82435(9) 0.0245(3) Uani 1 1 d . . . . .
C9 C 0.55835(17) 0.64110(11) 0.79362(10) 0.0287(3) Uani 1 1 d . . . . .
C10 C 0.68648(18) 0.73408(11) 0.85574(11) 0.0337(3) Uani 1 1 d . . . . .
H10A H 0.782063 0.725971 0.848639 0.051 Uiso 1 1 calc R U . . .
H10B H 0.690749 0.743603 0.919934 0.051 Uiso 1 1 calc R U . . .
H10C H 0.670661 0.793648 0.839400 0.051 Uiso 1 1 calc R U . . .
C11 C 0.46188(15) 0.39291(10) 0.82634(9) 0.0220(3) Uani 1 1 d . . . . .
C12 C 0.32914(15) 0.41821(11) 0.68140(9) 0.0238(3) Uani 1 1 d . . . . .
H12 H 0.380456 0.439830 0.638502 0.029 Uiso 1 1 calc R U . . .
C13 C 0.18679(17) 0.45515(12) 0.67538(10) 0.0298(3) Uani 1 1 d . . . . .
H13 H 0.205444 0.526824 0.713730 0.036 Uiso 1 1 calc R U . . .
C14 C 0.10908(17) 0.42761(13) 0.57251(10) 0.0337(3) Uani 1 1 d . . . . .
H14 H 0.102442 0.473838 0.538672 0.040 Uiso 1 1 calc R U . . .
C15 C 0.05200(18) 0.32676(14) 0.53852(11) 0.0384(4) Uani 1 1 d . . . . .
H15 H -0.001016 0.287771 0.475513 0.046 Uiso 1 1 calc R U . . .
C16 C 0.08631(16) 0.28471(13) 0.61795(11) 0.0334(3) Uani 1 1 d . . . . .
H16 H 0.019011 0.215159 0.607724 0.040 Uiso 1 1 calc R U . . .
C17 C 0.08294(18) 0.37132(14) 0.69661(11) 0.0363(4) Uani 1 1 d . . . . .
H17A H -0.019788 0.377696 0.688953 0.044 Uiso 1 1 calc R U . . .
H17B H 0.127596 0.366433 0.758355 0.044 Uiso 1 1 calc R U . . .
C18 C 0.26112(15) 0.30004(11) 0.64784(9) 0.0248(3) Uani 1 1 d . . . . .
H18 H 0.288585 0.270408 0.592473 0.030 Uiso 1 1 calc R U . . .
C19 C 0.29944(15) 0.24511(11) 0.71783(9) 0.0243(3) Uani 1 1 d . . . . .
O3 O 0.53586(13) -0.08631(8) 0.79394(8) 0.0373(3) Uani 1 1 d . . . . .
O4 O 0.75983(11) 0.38025(7) 0.77732(7) 0.0290(2) Uani 1 1 d . . . . .
N5 N 0.42466(12) 0.06651(8) 0.58381(8) 0.0222(2) Uani 1 1 d . . . . .
N6 N 0.37353(13) -0.02555(9) 0.59629(8) 0.0247(2) Uani 1 1 d . . . . .
N7 N 0.56832(12) 0.07981(8) 0.71836(8) 0.0222(2) Uani 1 1 d . . . . .
N8 N 0.60346(13) 0.23068(9) 0.67154(8) 0.0232(2) Uani 1 1 d . . . . .
C20 C 0.07733(18) 0.16327(13) 0.28576(11) 0.0359(3) Uani 1 1 d . . . . .
H20A H -0.028781 0.120770 0.265177 0.054 Uiso 1 1 calc R U . . .
H20B H 0.117135 0.151461 0.234124 0.054 Uiso 1 1 calc R U . . .
H20C H 0.083763 0.235176 0.307732 0.054 Uiso 1 1 calc R U . . .
C21 C 0.16921(16) 0.13628(11) 0.36290(9) 0.0266(3) Uani 1 1 d . . . . .
C22 C 0.10022(16) 0.06377(11) 0.39741(10) 0.0272(3) Uani 1 1 d . . . . .
H22 H -0.005959 0.030320 0.371034 0.033 Uiso 1 1 calc R U . . .
C23 C 0.18404(16) 0.03977(11) 0.46952(9) 0.0254(3) Uani 1 1 d . . . . .
H23 H 0.135715 -0.008903 0.493074 0.030 Uiso 1 1 calc R U . . .
C24 C 0.33960(15) 0.08787(10) 0.50682(9) 0.0217(3) Uani 1 1 d . . . . .
C25 C 0.41183(15) 0.15837(10) 0.47240(9) 0.0245(3) Uani 1 1 d . . . . .
H25 H 0.518608 0.189710 0.497222 0.029 Uiso 1 1 calc R U . . .
C26 C 0.32539(16) 0.18231(11) 0.40107(9) 0.0266(3) Uani 1 1 d . . . . .
H26 H 0.373996 0.231205 0.377825 0.032 Uiso 1 1 calc R U . . .
C27 C 0.46217(15) -0.01531(10) 0.67783(9) 0.0235(3) Uani 1 1 d . . . . .
C28 C 0.44518(16) -0.09740(11) 0.72033(10) 0.0285(3) Uani 1 1 d . . . . .
C29 C 0.31145(17) -0.19062(11) 0.66746(11) 0.0331(3) Uani 1 1 d . . . . .
H29A H 0.326391 -0.246890 0.689959 0.050 Uiso 1 1 calc R U . . .
H29B H 0.300856 -0.209092 0.601741 0.050 Uiso 1 1 calc R U . . .
H29C H 0.219498 -0.176947 0.676041 0.050 Uiso 1 1 calc R U . . .
C30 C 0.54070(14) 0.13388(10) 0.65970(9) 0.0215(3) Uani 1 1 d . . . . .
C31 C 0.68629(15) 0.12390(10) 0.80938(9) 0.0225(3) Uani 1 1 d . . . . .
H31 H 0.642784 0.110913 0.858106 0.027 Uiso 1 1 calc R U . . .
C32 C 0.82399(16) 0.08253(11) 0.81242(10) 0.0271(3) Uani 1 1 d . . . . .
H32 H 0.799273 0.007914 0.780843 0.032 Uiso 1 1 calc R U . . .
C33 C 0.91995(16) 0.12303(12) 0.91367(10) 0.0315(3) Uani 1 1 d . . . . .
H33 H 0.933412 0.084127 0.954153 0.038 Uiso 1 1 calc R U . . .
C34 C 0.98169(17) 0.22293(12) 0.93529(10) 0.0320(3) Uani 1 1 d . . . . .
H34 H 1.046539 0.268472 0.994293 0.038 Uiso 1 1 calc R U . . .
C35 C 0.93023(15) 0.25114(11) 0.84912(9) 0.0270(3) Uani 1 1 d . . . . .
H35 H 0.995162 0.316498 0.848274 0.032 Uiso 1 1 calc R U . . .
C36 C 0.91796(16) 0.15424(12) 0.77478(10) 0.0295(3) Uani 1 1 d . . . . .
H36A H 0.862435 0.150766 0.711645 0.035 Uiso 1 1 calc R U . . .
H36B H 1.017529 0.144126 0.777536 0.035 Uiso 1 1 calc R U . . .
C37 C 0.75767(15) 0.24036(10) 0.83093(9) 0.0225(3) Uani 1 1 d . . . . .
H37 H 0.744281 0.277783 0.889221 0.027 Uiso 1 1 calc R U . . .
C38 C 0.70472(15) 0.28700(10) 0.75687(9) 0.0227(3) Uani 1 1 d . . . . .
O5 O 0.27375(15) 0.02773(9) 0.79801(8) 0.0390(3) Uani 1 1 d . . . . .
C39 C 0.3175(2) 0.07442(13) 0.89453(11) 0.0388(4) Uani 1 1 d . . . . .
H39A H 0.258466 0.121281 0.908403 0.047 Uiso 1 1 calc R U . . .
H39B H 0.426360 0.114734 0.918840 0.047 Uiso 1 1 calc R U . . .
C40 C 0.2906(3) -0.00397(18) 0.93973(14) 0.0763(8) Uani 1 1 d . . . . .
H40A H 0.181525 -0.038952 0.920456 0.115 Uiso 1 1 calc R U . . .
H40B H 0.329954 0.028485 1.006874 0.115 Uiso 1 1 calc R U . . .
H40C H 0.342594 -0.053429 0.921827 0.115 Uiso 1 1 calc R U . . .
O6 O 0.71606(14) 0.52749(9) 0.69943(8) 0.0370(3) Uani 1 1 d . . . . .
C41 C 0.7378(2) 0.51893(13) 0.61289(11) 0.0414(4) Uani 1 1 d . . . . .
H41A H 0.845513 0.525288 0.620120 0.050 Uiso 1 1 calc R U . . .
H41B H 0.715517 0.575839 0.592745 0.050 Uiso 1 1 calc R U . . .
C42 C 0.6404(3) 0.42087(15) 0.54018(13) 0.0542(5) Uani 1 1 d . . . . .
H42A H 0.657185 0.420213 0.481480 0.081 Uiso 1 1 calc R U . . .
H42B H 0.533652 0.413512 0.533325 0.081 Uiso 1 1 calc R U . . .
H42C H 0.666361 0.364299 0.557866 0.081 Uiso 1 1 calc R U . . .
H6A H 0.724(2) 0.4723(16) 0.7131(14) 0.051(6) Uiso 1 1 d . . . . .
H5 H 0.272(2) 0.0768(18) 0.7719(15) 0.060(6) Uiso 1 1 d . . . . .
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
C11 N1 N2 111.50(10) . . ?
C11 N1 C5 127.79(11) . . ?
N2 N1 C5 119.73(11) . . ?
C8 N2 N1 104.37(11) . . ?
C11 N3 C8 107.29(11) . . ?
C11 N3 C12 122.66(11) . . ?
C8 N3 C12 129.67(11) . . ?
C11 N4 C19 116.07(11) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 118.38(12) . . ?
C7 C2 C1 120.40(13) . . ?
C3 C2 C1 121.21(13) . . ?
C4 C3 C2 121.04(13) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 119.35(13) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.97(12) . . ?
C4 C5 N1 119.17(12) . . ?
C6 C5 N1 119.80(12) . . ?
C5 C6 C7 118.68(13) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C6 C7 C2 121.51(13) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
N2 C8 N3 111.85(12) . . ?
N2 C8 C9 122.52(13) . . ?
N3 C8 C9 125.63(12) . . ?
O1 C9 C8 120.04(14) . . ?
O1 C9 C10 123.78(13) . . ?
C8 C9 C10 116.18(12) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N4 C11 N3 129.62(12) . . ?
N4 C11 N1 125.49(12) . . ?
N3 C11 N1 104.87(11) . . ?
N3 C12 C18 110.65(10) . . ?
N3 C12 C13 112.75(11) . . ?
C18 C12 C13 103.47(11) . . ?
N3 C12 H12 109.9 . . ?
C18 C12 H12 109.9 . . ?
C13 C12 H12 109.9 . . ?
C14 C13 C17 100.51(13) . . ?
C14 C13 C12 103.64(11) . . ?
C17 C13 C12 101.10(11) . . ?
C14 C13 H13 116.4 . . ?
C17 C13 H13 116.4 . . ?
C12 C13 H13 116.4 . . ?
C15 C14 C13 107.21(13) . . ?
C15 C14 H14 126.4 . . ?
C13 C14 H14 126.4 . . ?
C14 C15 C16 108.06(14) . . ?
C14 C15 H15 126.0 . . ?
C16 C15 H15 126.0 . . ?
C15 C16 C17 100.46(13) . . ?
C15 C16 C18 106.16(12) . . ?
C17 C16 C18 99.64(12) . . ?
C15 C16 H16 116.1 . . ?
C17 C16 H16 116.1 . . ?
C18 C16 H16 116.1 . . ?
C13 C17 C16 94.21(12) . . ?
C13 C17 H17A 112.9 . . ?
C16 C17 H17A 112.9 . . ?
C13 C17 H17B 112.9 . . ?
C16 C17 H17B 112.9 . . ?
H17A C17 H17B 110.3 . . ?
C19 C18 C12 117.74(11) . . ?
C19 C18 C16 108.84(11) . . ?
C12 C18 C16 101.85(11) . . ?
C19 C18 H18 109.3 . . ?
C12 C18 H18 109.3 . . ?
C16 C18 H18 109.3 . . ?
O2 C19 N4 120.11(12) . . ?
O2 C19 C18 117.15(12) . . ?
N4 C19 C18 122.74(12) . . ?
C30 N5 N6 111.56(10) . . ?
C30 N5 C24 127.51(11) . . ?
N6 N5 C24 119.76(11) . . ?
C27 N6 N5 104.49(11) . . ?
C30 N7 C27 107.18(11) . . ?
C30 N7 C31 122.89(11) . . ?
C27 N7 C31 129.82(11) . . ?
C30 N8 C38 115.68(11) . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 118.34(12) . . ?
C26 C21 C20 120.74(13) . . ?
C22 C21 C20 120.91(13) . . ?
C23 C22 C21 121.15(13) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C24 119.11(13) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C25 C24 C23 121.01(12) . . ?
C25 C24 N5 119.95(12) . . ?
C23 C24 N5 119.01(12) . . ?
C24 C25 C26 118.89(13) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?
C25 C26 C21 121.46(13) . . ?
C25 C26 H26 119.3 . . ?
C21 C26 H26 119.3 . . ?
N6 C27 N7 111.80(11) . . ?
N6 C27 C28 122.81(13) . . ?
N7 C27 C28 125.38(12) . . ?
O3 C28 C27 120.26(13) . . ?
O3 C28 C29 123.88(13) . . ?
C27 C28 C29 115.86(12) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N8 C30 N7 129.61(12) . . ?
N8 C30 N5 125.49(12) . . ?
N7 C30 N5 104.83(11) . . ?
N7 C31 C37 110.19(10) . . ?
N7 C31 C32 112.19(11) . . ?
C37 C31 C32 103.43(11) . . ?
N7 C31 H31 110.3 . . ?
C37 C31 H31 110.3 . . ?
C32 C31 H31 110.3 . . ?
C33 C32 C36 100.29(12) . . ?
C33 C32 C31 104.29(11) . . ?
C36 C32 C31 100.98(11) . . ?
C33 C32 H32 116.3 . . ?
C36 C32 H32 116.3 . . ?
C31 C32 H32 116.3 . . ?
C34 C33 C32 107.43(13) . . ?
C34 C33 H33 126.3 . . ?
C32 C33 H33 126.3 . . ?
C33 C34 C35 107.77(13) . . ?
C33 C34 H34 126.1 . . ?
C35 C34 H34 126.1 . . ?
C34 C35 C36 100.52(12) . . ?
C34 C35 C37 106.04(11) . . ?
C36 C35 C37 100.18(11) . . ?
C34 C35 H35 115.9 . . ?
C36 C35 H35 116.0 . . ?
C37 C35 H35 116.0 . . ?
C32 C36 C35 93.93(11) . . ?
C32 C36 H36A 112.9 . . ?
C35 C36 H36A 112.9 . . ?
C32 C36 H36B 112.9 . . ?
C35 C36 H36B 112.9 . . ?
H36A C36 H36B 110.4 . . ?
C38 C37 C31 118.16(11) . . ?
C38 C37 C35 109.28(11) . . ?
C31 C37 C35 101.95(10) . . ?
C38 C37 H37 109.0 . . ?
C31 C37 H37 109.0 . . ?
C35 C37 H37 109.0 . . ?
O4 C38 N8 120.54(12) . . ?
O4 C38 C37 116.55(12) . . ?
N8 C38 C37 122.91(12) . . ?
C39 O5 H5 107.7(14) . . ?
O5 C39 C40 110.03(15) . . ?
O5 C39 H39A 109.7 . . ?
C40 C39 H39A 109.7 . . ?
O5 C39 H39B 109.7 . . ?
C40 C39 H39B 109.7 . . ?
H39A C39 H39B 108.2 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C41 O6 H6A 108.3(13) . . ?
O6 C41 C42 112.98(14) . . ?
O6 C41 H41A 109.0 . . ?
C42 C41 H41A 109.0 . . ?
O6 C41 H41B 109.0 . . ?
C42 C41 H41B 109.0 . . ?
H41A C41 H41B 107.8 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 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 C9 1.2123(17) . yes
O2 C19 1.2339(17) . yes
N1 C11 1.3667(17) . yes
N1 N2 1.3769(16) . yes
N1 C5 1.4269(16) . yes
N2 C8 1.3086(17) . yes
N3 C11 1.3615(16) . yes
N3 C8 1.3740(18) . yes
N3 C12 1.4677(16) . yes
N4 C11 1.3155(18) . yes
N4 C19 1.3648(17) . yes
C1 C2 1.5069(18) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.392(2) . ?
C2 C3 1.393(2) . ?
C3 C4 1.3896(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3857(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3897(19) . ?
C6 C7 1.3918(18) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.4883(19) . ?
C9 C10 1.494(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 C18 1.557(2) . ?
C12 C13 1.5623(18) . ?
C12 H12 1.0000 . ?
C13 C14 1.516(2) . ?
C13 C17 1.534(2) . ?
C13 H13 1.0000 . ?
C14 C15 1.329(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.518(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.535(2) . ?
C16 C18 1.5693(19) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5275(19) . ?
C18 H18 1.0000 . ?
O3 C28 1.2142(17) . yes
O4 C38 1.2372(17) . yes
N5 C30 1.3668(17) . yes
N5 N6 1.3727(15) . yes
N5 C24 1.4287(16) . yes
N6 C27 1.3064(17) . yes
N7 C30 1.3607(16) . yes
N7 C27 1.3760(17) . yes
N7 C31 1.4679(16) . yes
N8 C30 1.3179(17) . yes
N8 C38 1.3625(17) . yes
C20 C21 1.5043(19) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C26 1.391(2) . ?
C21 C22 1.397(2) . ?
C22 C23 1.3872(19) . ?
C22 H22 0.9500 . ?
C23 C24 1.3891(18) . ?
C23 H23 0.9500 . ?
C24 C25 1.3885(19) . ?
C25 C26 1.3886(18) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.4855(19) . ?
C28 C29 1.496(2) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C31 C37 1.5566(19) . ?
C31 C32 1.5605(18) . ?
C31 H31 1.0000 . ?
C32 C33 1.518(2) . ?
C32 C36 1.536(2) . ?
C32 H32 1.0000 . ?
C33 C34 1.329(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.513(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.536(2) . ?
C35 C37 1.5703(18) . ?
C35 H35 1.0000 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.5220(18) . ?
C37 H37 1.0000 . ?
O5 C39 1.4138(19) . yes
O5 H5 0.90(2) . ?
C39 C40 1.478(3) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
O6 C41 1.4167(19) . ?
O6 H6A 0.88(2) . ?
C41 C42 1.488(2) . yes
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 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
_geom_hbond_publ_flag
C6 H6 N4 0.95 2.49 2.9668(17) 111.1 . yes
C29 H29A O1 0.98 2.45 3.3465(18) 151.9 1_545 yes
O6 H6A O4 0.88(2) 1.89(2) 2.7447(15) 163.5(19) . yes
O5 H5 O2 0.90(2) 1.87(2) 2.7479(15) 166(2) . yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168341645
