#------------------------------------------------------------------------------
#$Date: 2024-08-05 22:46:26 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293896 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/32/7063291.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_7063291
loop_
_publ_author_name
'El Bakri, Youness'
'Siddique, Sabir Ali'
'Mohamed, Shaaban K.'
'Sarfraz, Muhammad'
'Abuelizz, Hatem A.'
'Al-Salahi, Rashad'
'Mague, Joel T.'
'Ahmed, Eman A.'
_publ_section_title
;
 Synthesis, investigation of the crystal structure, DFT calculations, and
 in silico medicinal potential of hydrazono- and aminomethylene
 substituted pyrazolidine-3,5-diones as potential anticancer scaffolds
;
_journal_issue                   28
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12591
_journal_page_last               12608
_journal_paper_doi               10.1039/D4NJ01839G
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C15 H12 N4 O2'
_chemical_formula_sum            'C15 H12 N4 O2'
_chemical_formula_weight         280.29
_chemical_name_systematic
(E)-1-phenyl-4-((pyridin-2-ylamino)methylene)pyrazolidine-3,5-dione
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2024-04-20 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                102.548(4)
_cell_angle_beta                 94.531(4)
_cell_angle_gamma                95.302(4)
_cell_formula_units_Z            4
_cell_length_a                   6.1973(8)
_cell_length_b                   10.2465(13)
_cell_length_c                   20.461(3)
_cell_measurement_reflns_used    8011
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      28.208
_cell_measurement_theta_min      2.490
_cell_volume                     1256.2(3)
_computing_cell_refinement       'SAINT (Bruker, 2021)'
_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_data_reduction        'SAINT (Bruker, 2021)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2021)'
_computing_structure_refinement
'SHELXL-2018/1 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      125(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.890
_diffrn_measured_fraction_theta_max 0.834
_diffrn_measurement_device       'Bruker D8 QUEST PHOTON 3 diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 3 diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_Laue_measured_fraction_full 0.890
_diffrn_reflns_Laue_measured_fraction_max 0.834
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6336
_diffrn_reflns_point_group_measured_fraction_full 0.890
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        25.750
_diffrn_reflns_theta_max         28.512
_diffrn_reflns_theta_min         2.049
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.50
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Sheldrick, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.058
_exptl_transmission_factor_max   0.942
_exptl_transmission_factor_min   0.831
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         6336
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0856
_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)+(0.0577P)²+4.9083P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2151
_refine_ls_wR_factor_ref         0.2266
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4661
_reflns_number_total             6336
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj01839g2.cif
_cod_data_source_block           jtm1543_5
_cod_depositor_comments
'Adding full bibliography for 7063290--7063291.cif.'
_cod_original_cell_volume        1256.3(3)
_cod_database_code               7063291
_shelx_shelxl_version_number     2019/1
_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   0.994
_iucr_geom_hbonds_special_details
;
Cg3 and Cg5 are the centroids, respectively, of the C1...C6 and the 
C26...C30/N8 rings.
;
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 -0.3104(6) 0.3211(4) -0.0369(2) 0.0264(9) Uani 1 1 d . . . . .
O2 O 0.2984(6) 0.1606(4) 0.0605(2) 0.0279(10) Uani 1 1 d . . . . .
N1 N -0.0756(7) 0.1339(5) 0.0653(2) 0.0217(10) Uani 1 1 d . . . . .
N2 N -0.2569(7) 0.1740(5) 0.0325(2) 0.0216(10) Uani 1 1 d D . . . .
H2 H -0.394(4) 0.172(6) 0.045(3) 0.032 Uiso 1 1 d D U . . .
N3 N 0.0860(7) 0.4102(5) -0.0762(2) 0.0220(10) Uani 1 1 d D . . . .
H3 H -0.062(2) 0.398(6) -0.076(3) 0.033 Uiso 1 1 d D U . . .
N4 N 0.0556(8) 0.5448(5) -0.1508(2) 0.0245(11) Uani 1 1 d . . . . .
C1 C -0.1061(9) 0.0412(5) 0.1066(3) 0.0191(11) Uani 1 1 d . . . . .
C2 C 0.0744(9) 0.0087(6) 0.1431(3) 0.0233(12) Uani 1 1 d . . . . .
H2A H 0.217444 0.047867 0.140260 0.028 Uiso 1 1 calc R U . . .
C3 C 0.0385(9) -0.0826(6) 0.1838(3) 0.0261(13) Uani 1 1 d . . . . .
H3A H 0.159466 -0.107463 0.208008 0.031 Uiso 1 1 calc R U . . .
C4 C -0.1676(9) -0.1373(6) 0.1897(3) 0.0252(13) Uani 1 1 d . . . . .
H4 H -0.187915 -0.196668 0.219098 0.030 Uiso 1 1 calc R U . . .
C5 C -0.3459(9) -0.1068(6) 0.1533(3) 0.0257(13) Uani 1 1 d . . . . .
H5 H -0.488178 -0.146405 0.156585 0.031 Uiso 1 1 calc R U . . .
C6 C -0.3147(9) -0.0173(6) 0.1116(3) 0.0239(12) Uani 1 1 d . . . . .
H6A H -0.436562 0.004106 0.086426 0.029 Uiso 1 1 calc R U . . .
C7 C -0.1875(9) 0.2607(5) -0.0051(3) 0.0210(12) Uani 1 1 d . . . . .
C8 C 0.0468(8) 0.2670(5) -0.0018(3) 0.0206(12) Uani 1 1 d . . . . .
C9 C 0.1156(10) 0.1860(6) 0.0434(3) 0.0244(12) Uani 1 1 d . . . . .
C10 C 0.1742(9) 0.3384(5) -0.0360(3) 0.0199(11) Uani 1 1 d . . . . .
H10 H 0.327705 0.337271 -0.031127 0.024 Uiso 1 1 calc R U . . .
C11 C 0.1944(9) 0.4842(5) -0.1167(3) 0.0204(11) Uani 1 1 d . . . . .
C12 C 0.4177(9) 0.4909(6) -0.1216(3) 0.0251(13) Uani 1 1 d . . . . .
H12 H 0.508959 0.445190 -0.096873 0.030 Uiso 1 1 calc R U . . .
C13 C 0.5024(10) 0.5674(6) -0.1643(3) 0.0298(14) Uani 1 1 d . . . . .
H13 H 0.654176 0.575976 -0.168806 0.036 Uiso 1 1 calc R U . . .
C14 C 0.3632(10) 0.6304(6) -0.1999(3) 0.0307(14) Uani 1 1 d . . . . .
H14 H 0.416222 0.682555 -0.229633 0.037 Uiso 1 1 calc R U . . .
C15 C 0.1443(10) 0.6155(6) -0.1912(3) 0.0290(13) Uani 1 1 d . . . . .
H15 H 0.049594 0.659169 -0.216024 0.035 Uiso 1 1 calc R U . . .
O3 O 0.7958(7) 0.6586(4) 0.4633(2) 0.0298(10) Uani 1 1 d . . . . .
O4 O 0.2507(7) 0.9088(4) 0.5613(2) 0.0327(11) Uani 1 1 d . . . . .
N5 N 0.6284(7) 0.9346(5) 0.5683(2) 0.0247(11) Uani 1 1 d . . . . .
N6 N 0.7891(8) 0.8652(5) 0.5355(3) 0.0242(11) Uani 1 1 d D . . . .
H6 H 0.932(3) 0.898(6) 0.545(3) 0.036 Uiso 1 1 d D U . . .
N7 N 0.3712(8) 0.5346(5) 0.4240(3) 0.0280(11) Uani 1 1 d D . . . .
H7 H 0.506(5) 0.511(6) 0.415(3) 0.042 Uiso 1 1 d D U . . .
N8 N 0.3441(8) 0.3296(5) 0.3502(3) 0.0288(12) Uani 1 1 d . . . . .
C16 C 0.6869(10) 1.0608(6) 0.6128(3) 0.0249(13) Uani 1 1 d . . . . .
C17 C 0.5393(10) 1.1204(7) 0.6547(3) 0.0324(15) Uani 1 1 d . . . . .
H17 H 0.397189 1.075873 0.653582 0.039 Uiso 1 1 calc R U . . .
C18 C 0.5999(10) 1.2438(6) 0.6976(3) 0.0324(15) Uani 1 1 d . . . . .
H18 H 0.497753 1.283793 0.725748 0.039 Uiso 1 1 calc R U . . .
C19 C 0.8054(10) 1.3113(6) 0.7009(3) 0.0302(14) Uani 1 1 d . . . . .
H19 H 0.845203 1.396091 0.731255 0.036 Uiso 1 1 calc R U . . .
C20 C 0.9523(10) 1.2532(6) 0.6591(3) 0.0305(14) Uani 1 1 d . . . . .
H20 H 1.094109 1.298445 0.660580 0.037 Uiso 1 1 calc R U . . .
C21 C 0.8934(10) 1.1292(6) 0.6152(3) 0.0256(13) Uani 1 1 d . . . . .
H21 H 0.994875 1.090370 0.586501 0.031 Uiso 1 1 calc R U . . .
C22 C 0.6954(10) 0.7462(6) 0.4956(3) 0.0254(13) Uani 1 1 d . . . . .
C23 C 0.4638(9) 0.7444(6) 0.4982(3) 0.0239(12) Uani 1 1 d . . . . .
C24 C 0.4233(9) 0.8658(6) 0.5446(3) 0.0259(13) Uani 1 1 d . . . . .
C25 C 0.3102(10) 0.6418(6) 0.4646(3) 0.0266(13) Uani 1 1 d . . . . .
H25 H 0.160433 0.647372 0.470298 0.032 Uiso 1 1 calc R U . . .
C26 C 0.2360(9) 0.4220(6) 0.3862(3) 0.0239(13) Uani 1 1 d . . . . .
C27 C 0.0114(10) 0.4075(6) 0.3881(3) 0.0271(13) Uani 1 1 d . . . . .
H27 H -0.059225 0.475870 0.414463 0.033 Uiso 1 1 calc R U . . .
C28 C -0.1060(11) 0.2903(6) 0.3502(3) 0.0315(14) Uani 1 1 d . . . . .
H28 H -0.259790 0.277357 0.350101 0.038 Uiso 1 1 calc R U . . .
C29 C 0.0013(10) 0.1914(6) 0.3124(3) 0.0300(14) Uani 1 1 d . . . . .
H29 H -0.075797 0.109755 0.286468 0.036 Uiso 1 1 calc R U . . .
C30 C 0.2263(10) 0.2171(6) 0.3140(3) 0.0317(14) Uani 1 1 d . . . . .
H30 H 0.301134 0.150722 0.287936 0.038 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
C9 N1 N2 109.6(4) . . ?
C9 N1 C1 130.1(5) . . ?
N2 N1 C1 119.9(4) . . ?
C7 N2 N1 109.2(4) . . ?
C7 N2 H2 121(4) . . ?
N1 N2 H2 126(4) . . ?
C10 N3 C11 127.4(5) . . ?
C10 N3 H3 108(4) . . ?
C11 N3 H3 125(4) . . ?
C15 N4 C11 115.7(5) . . ?
C6 C1 C2 119.9(5) . . ?
C6 C1 N1 120.4(5) . . ?
C2 C1 N1 119.7(5) . . ?
C3 C2 C1 118.2(5) . . ?
C3 C2 H2A 120.9 . . ?
C1 C2 H2A 120.9 . . ?
C4 C3 C2 121.5(5) . . ?
C4 C3 H3A 119.3 . . ?
C2 C3 H3A 119.3 . . ?
C3 C4 C5 120.5(5) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 119.3(5) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 120.6(5) . . ?
C5 C6 H6A 119.7 . . ?
C1 C6 H6A 119.7 . . ?
O1 C7 N2 124.5(5) . . ?
O1 C7 C8 127.9(5) . . ?
N2 C7 C8 107.6(5) . . ?
C10 C8 C9 127.6(5) . . ?
C10 C8 C7 124.7(5) . . ?
C9 C8 C7 107.6(5) . . ?
O2 C9 N1 124.0(5) . . ?
O2 C9 C8 130.4(6) . . ?
N1 C9 C8 105.6(5) . . ?
N3 C10 C8 120.8(5) . . ?
N3 C10 H10 119.6 . . ?
C8 C10 H10 119.6 . . ?
N4 C11 C12 124.4(5) . . ?
N4 C11 N3 111.7(5) . . ?
C12 C11 N3 123.8(5) . . ?
C11 C12 C13 117.4(5) . . ?
C11 C12 H12 121.3 . . ?
C13 C12 H12 121.3 . . ?
C14 C13 C12 119.2(6) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 118.0(6) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 H14 121.0 . . ?
N4 C15 C14 125.1(6) . . ?
N4 C15 H15 117.4 . . ?
C14 C15 H15 117.4 . . ?
C24 N5 N6 109.8(5) . . ?
C24 N5 C16 129.9(5) . . ?
N6 N5 C16 120.0(5) . . ?
C22 N6 N5 109.6(5) . . ?
C22 N6 H6 130(4) . . ?
N5 N6 H6 120(4) . . ?
C25 N7 C26 127.1(5) . . ?
C25 N7 H7 131(4) . . ?
C26 N7 H7 102(4) . . ?
C26 N8 C30 117.1(5) . . ?
C21 C16 C17 118.7(6) . . ?
C21 C16 N5 120.4(5) . . ?
C17 C16 N5 120.9(5) . . ?
C18 C17 C16 119.8(6) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 121.7(6) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C20 118.8(6) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C19 C20 C21 120.2(6) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 120.7(6) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
O3 C22 N6 125.0(5) . . ?
O3 C22 C23 128.0(6) . . ?
N6 C22 C23 106.9(5) . . ?
C25 C23 C22 125.4(6) . . ?
C25 C23 C24 126.3(6) . . ?
C22 C23 C24 108.2(5) . . ?
O4 C24 N5 123.7(6) . . ?
O4 C24 C23 131.1(6) . . ?
N5 C24 C23 105.2(5) . . ?
N7 C25 C23 119.9(6) . . ?
N7 C25 H25 120.0 . . ?
C23 C25 H25 120.0 . . ?
N8 C26 C27 123.8(6) . . ?
N8 C26 N7 113.6(5) . . ?
C27 C26 N7 122.6(5) . . ?
C28 C27 C26 117.8(6) . . ?
C28 C27 H27 121.1 . . ?
C26 C27 H27 121.1 . . ?
C27 C28 C29 120.0(6) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 C30 117.2(6) . . ?
C28 C29 H29 121.4 . . ?
C30 C29 H29 121.4 . . ?
N8 C30 C29 124.1(6) . . ?
N8 C30 H30 117.9 . . ?
C29 C30 H30 117.9 . . ?
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 C7 1.252(6) . ?
O2 C9 1.227(7) . ?
N1 C9 1.401(7) . ?
N1 N2 1.403(6) . ?
N1 C1 1.411(7) . ?
N2 C7 1.358(7) . ?
N2 H2 0.911(11) . ?
N3 C10 1.336(7) . ?
N3 C11 1.406(7) . ?
N3 H3 0.913(11) . ?
N4 C15 1.331(7) . ?
N4 C11 1.343(7) . ?
C1 C6 1.395(8) . ?
C1 C2 1.403(7) . ?
C2 C3 1.396(8) . ?
C2 H2A 0.9500 . ?
C3 C4 1.371(8) . ?
C3 H3A 0.9500 . ?
C4 C5 1.383(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(8) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.443(7) . ?
C8 C10 1.360(7) . ?
C8 C9 1.436(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(7) . ?
C12 C13 1.396(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(8) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
O3 C22 1.241(7) . ?
O4 C24 1.239(7) . ?
N5 C24 1.391(7) . ?
N5 N6 1.406(6) . ?
N5 C16 1.408(7) . ?
N6 C22 1.361(7) . ?
N6 H6 0.909(11) . ?
N7 C25 1.330(7) . ?
N7 C26 1.401(7) . ?
N7 H7 0.913(11) . ?
N8 C26 1.334(7) . ?
N8 C30 1.342(8) . ?
C16 C21 1.393(8) . ?
C16 C17 1.394(8) . ?
C17 C18 1.374(8) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(9) . ?
C18 H18 0.9500 . ?
C19 C20 1.384(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(8) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.439(8) . ?
C23 C25 1.372(8) . ?
C23 C24 1.446(8) . ?
C25 H25 0.9500 . ?
C26 C27 1.391(8) . ?
C27 C28 1.385(8) . ?
C27 H27 0.9500 . ?
C28 C29 1.390(8) . ?
C28 H28 0.9500 . ?
C29 C30 1.391(8) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
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
N2 H2 O2 0.911(11) 1.950(15) 2.856(6) 172(6) 1_455 yes
N3 H3 O1 0.913(11) 1.97(4) 2.781(6) 148(6) . yes
C2 H2A O2 0.95 2.26 2.885(7) 123 . yes
C6 H6A O2 0.95 2.50 3.377(7) 153 1_455 yes
C10 H10 O1 0.95 2.27 3.216(7) 171 1_655 yes
C12 H12 O1 0.95 2.26 3.204(7) 173 1_655 yes
C13 H13 N4 0.95 2.55 3.451(8) 159 1_655 y
C15 H15 Cg5 0.95 2.95 3.782(7) 147 2_565 y
N6 H6 O4 0.909(11) 1.97(2) 2.843(6) 162(6) 1_655 yes
N7 H7 O3 0.913(11) 2.24(6) 2.791(6) 118(5) . yes
C17 H17 O4 0.95 2.32 2.915(8) 121 . yes
C21 H21 O4 0.95 2.55 3.384(7) 147 1_655 yes
C25 H25 O3 0.95 2.27 3.207(7) 170 1_455 yes
C27 H27 O3 0.95 2.23 3.164(7) 170 1_455 yes
C28 H28 N8 0.95 2.56 3.468(9) 160 1_455 y
C29 H29 Cg3 0.95 2.92 3.697(7) 140 . y
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 C7 -5.7(6) . . . . ?
C1 N1 N2 C7 -178.7(5) . . . . ?
C9 N1 C1 C6 -167.4(5) . . . . ?
N2 N1 C1 C6 3.9(8) . . . . ?
C9 N1 C1 C2 13.3(9) . . . . ?
N2 N1 C1 C2 -175.4(5) . . . . ?
C6 C1 C2 C3 0.1(8) . . . . ?
N1 C1 C2 C3 179.5(5) . . . . ?
C1 C2 C3 C4 -1.6(9) . . . . ?
C2 C3 C4 C5 2.4(9) . . . . ?
C3 C4 C5 C6 -1.5(9) . . . . ?
C4 C5 C6 C1 0.0(9) . . . . ?
C2 C1 C6 C5 0.7(9) . . . . ?
N1 C1 C6 C5 -178.7(5) . . . . ?
N1 N2 C7 O1 -175.1(5) . . . . ?
N1 N2 C7 C8 5.7(6) . . . . ?
O1 C7 C8 C10 -2.6(10) . . . . ?
N2 C7 C8 C10 176.5(5) . . . . ?
O1 C7 C8 C9 177.2(6) . . . . ?
N2 C7 C8 C9 -3.7(6) . . . . ?
N2 N1 C9 O2 -175.4(5) . . . . ?
C1 N1 C9 O2 -3.4(10) . . . . ?
N2 N1 C9 C8 3.3(6) . . . . ?
C1 N1 C9 C8 175.2(5) . . . . ?
C10 C8 C9 O2 -1.5(11) . . . . ?
C7 C8 C9 O2 178.7(6) . . . . ?
C10 C8 C9 N1 180.0(6) . . . . ?
C7 C8 C9 N1 0.2(6) . . . . ?
C11 N3 C10 C8 -177.2(5) . . . . ?
C9 C8 C10 N3 -179.6(5) . . . . ?
C7 C8 C10 N3 0.1(9) . . . . ?
C15 N4 C11 C12 -0.3(9) . . . . ?
C15 N4 C11 N3 -179.0(5) . . . . ?
C10 N3 C11 N4 -179.8(5) . . . . ?
C10 N3 C11 C12 1.4(9) . . . . ?
N4 C11 C12 C13 0.8(9) . . . . ?
N3 C11 C12 C13 179.4(5) . . . . ?
C11 C12 C13 C14 -0.9(9) . . . . ?
C12 C13 C14 C15 0.5(10) . . . . ?
C11 N4 C15 C14 -0.2(9) . . . . ?
C13 C14 C15 N4 0.1(10) . . . . ?
C24 N5 N6 C22 -5.7(7) . . . . ?
C16 N5 N6 C22 179.7(5) . . . . ?
C24 N5 C16 C21 -161.3(6) . . . . ?
N6 N5 C16 C21 12.1(8) . . . . ?
C24 N5 C16 C17 18.0(10) . . . . ?
N6 N5 C16 C17 -168.6(5) . . . . ?
C21 C16 C17 C18 -0.5(10) . . . . ?
N5 C16 C17 C18 -179.8(6) . . . . ?
C16 C17 C18 C19 -0.4(10) . . . . ?
C17 C18 C19 C20 0.8(10) . . . . ?
C18 C19 C20 C21 -0.3(9) . . . . ?
C19 C20 C21 C16 -0.5(9) . . . . ?
C17 C16 C21 C20 0.9(9) . . . . ?
N5 C16 C21 C20 -179.7(5) . . . . ?
N5 N6 C22 O3 -175.3(6) . . . . ?
N5 N6 C22 C23 5.2(6) . . . . ?
O3 C22 C23 C25 0.3(11) . . . . ?
N6 C22 C23 C25 179.8(6) . . . . ?
O3 C22 C23 C24 177.6(6) . . . . ?
N6 C22 C23 C24 -2.9(7) . . . . ?
N6 N5 C24 O4 -174.8(6) . . . . ?
C16 N5 C24 O4 -0.9(10) . . . . ?
N6 N5 C24 C23 3.6(6) . . . . ?
C16 N5 C24 C23 177.6(6) . . . . ?
C25 C23 C24 O4 -4.9(11) . . . . ?
C22 C23 C24 O4 177.8(6) . . . . ?
C25 C23 C24 N5 176.8(6) . . . . ?
C22 C23 C24 N5 -0.5(7) . . . . ?
C26 N7 C25 C23 -179.9(5) . . . . ?
C22 C23 C25 N7 -2.1(10) . . . . ?
C24 C23 C25 N7 -178.9(5) . . . . ?
C30 N8 C26 C27 0.0(9) . . . . ?
C30 N8 C26 N7 178.3(5) . . . . ?
C25 N7 C26 N8 -179.8(6) . . . . ?
C25 N7 C26 C27 -1.5(9) . . . . ?
N8 C26 C27 C28 0.0(9) . . . . ?
N7 C26 C27 C28 -178.1(6) . . . . ?
C26 C27 C28 C29 0.4(9) . . . . ?
C27 C28 C29 C30 -0.8(9) . . . . ?
C26 N8 C30 C29 -0.4(9) . . . . ?
C28 C29 C30 N8 0.8(10) . . . . ?
