# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_skm361a_a
_database_code_depnum_ccdc_archive 'CCDC 2349822'
loop_
_audit_author_name
_audit_author_address
'Joel T Mague'
;South ural state university
Russia
;
_audit_update_record             
;
2024-04-20 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_publcif_datablock.id            {400f9b57-2044-4ccd-9b02-0a24087acf1b}

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        
(Z)-4-(2-(4-bromophenyl)hydrazineylidene)-1-phenylpyrazolidine-3,5-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 Br N4 O2'
_chemical_formula_sum            'C15 H11 Br N4 O2'
_chemical_formula_weight         359.19

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   16.1068(17)
_cell_length_b                   5.7977(6)
_cell_length_c                   7.4341(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.755(4)
_cell_angle_gamma                90
_cell_volume                     691.82(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9684
_cell_measurement_theta_min      2.5379
_cell_measurement_theta_max      32.0623
_cell_measurement_temperature    125.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   0.317
_exptl_transmission_factor_max   0.616
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.984
_shelx_estimated_absorpt_T_min   0.447
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           
;
The diffraction data were obtained from 9 sets of frames,
each of width 0.5° in ω or φ, collected with scan parameters
determined by the "strategy" routine in APEX4. The scan
time was 15 sec/frame.
;

_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?
_diffrn_source_power             1.50
_diffrn_source_current           30.0
_diffrn_source_voltage           50

_diffrn_radiation_monochromator  graphite

_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_detector_area_resol_mean 7.3910

_diffrn_reflns_number            28969
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.538
_diffrn_reflns_theta_max         32.131
_diffrn_reflns_theta_full        32.100
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4805
_reflns_number_gt                4278
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.977
_reflns_Friedel_fraction_max     0.977
_reflns_Friedel_fraction_full    0.979

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_cell_refinement       'SAINT (Bruker, 2021)'
_computing_data_reduction        'SAINT (Bruker, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL-2018/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2021)'

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. H-atoms attached to carbon 
were placed in calculated positions (C---H = 0.95 Å) and were 
included as riding contributions with isotropic displacement parameters 
1.2 times those of the attached atoms. Those attached to nitrogen 
were placed in locations derived from a difference map and refined with 
a DFIX 0.91 0.01 instruction.  Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0640P)²+0.1076P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.046(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4805
_refine_ls_number_parameters     208
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1092
_refine_ls_wR_factor_gt          0.1060
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Br1 Br 0.92070(4) 0.13745(9) 0.71107(5) 0.03740(15) Uani 1 1 d . . . . .
O1 O 0.38761(18) 0.3909(4) 0.5655(4) 0.0193(5) Uani 1 1 d . . . . .
O2 O 0.48684(18) 1.0612(5) 0.2897(4) 0.0218(5) Uani 1 1 d . . . . .
N1 N 0.33421(18) 0.7549(5) 0.4900(4) 0.0150(5) Uani 1 1 d . . . . .
N2 N 0.36192(19) 0.9503(5) 0.3932(4) 0.0160(5) Uani 1 1 d D . . . .
H2A H 0.366(4) 1.079(7) 0.461(8) 0.033(15) Uiso 1 1 d D . . . .
N3 N 0.5450(2) 0.6153(5) 0.4417(4) 0.0171(5) Uani 1 1 d . . . . .
N4 N 0.5633(2) 0.4156(5) 0.5156(4) 0.0180(5) Uani 1 1 d D . . . .
H4A H 0.520(4) 0.336(13) 0.555(13) 0.07(3) Uiso 1 1 d D . . . .
C1 C 0.2501(2) 0.7449(6) 0.5268(4) 0.0138(5) Uani 1 1 d . . . . .
C2 C 0.2205(2) 0.5576(6) 0.6225(5) 0.0179(6) Uani 1 1 d . . . . .
H2 H 0.257195 0.436866 0.663623 0.021 Uiso 1 1 calc R U . . .
C3 C 0.1373(2) 0.5506(7) 0.6565(5) 0.0201(7) Uani 1 1 d . . . . .
H3 H 0.117213 0.422746 0.720014 0.024 Uiso 1 1 calc R U . . .
C4 C 0.0825(2) 0.7268(7) 0.5997(5) 0.0197(6) Uani 1 1 d . . . . .
H4 H 0.025500 0.719662 0.623677 0.024 Uiso 1 1 calc R U . . .
C5 C 0.1129(2) 0.9151(6) 0.5063(5) 0.0187(6) Uani 1 1 d . . . . .
H5 H 0.076283 1.037126 0.467691 0.022 Uiso 1 1 calc R U . . .
C6 C 0.1960(2) 0.9247(6) 0.4697(5) 0.0166(6) Uani 1 1 d . . . . .
H6 H 0.216165 1.052635 0.406210 0.020 Uiso 1 1 calc R U . . .
C7 C 0.3945(2) 0.5876(6) 0.5043(5) 0.0148(6) Uani 1 1 d . . . . .
C8 C 0.4678(2) 0.6876(6) 0.4308(5) 0.0157(6) Uani 1 1 d . . . . .
C9 C 0.4453(2) 0.9155(6) 0.3629(5) 0.0168(6) Uani 1 1 d . . . . .
C10 C 0.6467(2) 0.3444(6) 0.5452(5) 0.0171(6) Uani 1 1 d . . . . .
C11 C 0.6626(2) 0.1305(6) 0.6255(5) 0.0195(6) Uani 1 1 d . . . . .
H11 H 0.617975 0.030822 0.649413 0.023 Uiso 1 1 calc R U . . .
C12 C 0.7450(3) 0.0644(7) 0.6705(5) 0.0213(7) Uani 1 1 d . . . . .
H12 H 0.757181 -0.081099 0.725276 0.026 Uiso 1 1 calc R U . . .
C13 C 0.8089(2) 0.2128(7) 0.6346(5) 0.0218(7) Uani 1 1 d . . . . .
C14 C 0.7935(2) 0.4229(7) 0.5478(6) 0.0223(7) Uani 1 1 d . . . . .
H14 H 0.838284 0.519630 0.519677 0.027 Uiso 1 1 calc R U . . .
C15 C 0.7114(2) 0.4885(7) 0.5029(5) 0.0195(6) Uani 1 1 d . . . . .
H15 H 0.699474 0.631254 0.443457 0.023 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Br1 C13 1.895(4) . ?
O1 C7 1.236(4) . ?
O2 C9 1.232(4) . ?
N1 C7 1.370(4) . ?
N1 C1 1.406(4) . ?
N1 N2 1.433(4) . ?
N2 C9 1.395(5) . ?
N2 H2A 0.897(14) . ?
N3 N4 1.304(4) . ?
N3 C8 1.310(5) . ?
N4 C10 1.405(5) . ?
N4 H4A 0.908(15) . ?
C1 C6 1.401(5) . ?
C1 C2 1.403(5) . ?
C2 C3 1.384(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.404(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.460(5) . ?
C8 C9 1.450(5) . ?
C10 C11 1.391(5) . ?
C10 C15 1.392(5) . ?
C11 C12 1.396(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(6) . ?
C14 C15 1.390(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

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
C7 N1 C1 130.1(3) . . ?
C7 N1 N2 110.5(3) . . ?
C1 N1 N2 118.4(3) . . ?
C9 N2 N1 108.1(3) . . ?
C9 N2 H2A 101(5) . . ?
N1 N2 H2A 113(4) . . ?
N4 N3 C8 119.3(3) . . ?
N3 N4 C10 120.4(3) . . ?
N3 N4 H4A 116(6) . . ?
C10 N4 H4A 124(6) . . ?
C6 C1 C2 120.1(3) . . ?
C6 C1 N1 119.7(3) . . ?
C2 C1 N1 120.2(3) . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 118.8(3) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
O1 C7 N1 126.6(3) . . ?
O1 C7 C8 127.1(3) . . ?
N1 C7 C8 106.2(3) . . ?
N3 C8 C9 121.4(3) . . ?
N3 C8 C7 130.0(3) . . ?
C9 C8 C7 107.8(3) . . ?
O2 C9 N2 122.5(3) . . ?
O2 C9 C8 130.5(3) . . ?
N2 C9 C8 106.9(3) . . ?
C11 C10 C15 121.2(3) . . ?
C11 C10 N4 118.0(3) . . ?
C15 C10 N4 120.8(3) . . ?
C10 C11 C12 119.0(4) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C13 C12 C11 119.4(4) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 121.9(4) . . ?
C12 C13 Br1 120.1(3) . . ?
C14 C13 Br1 118.0(3) . . ?
C15 C14 C13 118.7(4) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C10 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
C10 C15 H15 120.1 . . ?

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
C7 N1 N2 C9 -6.5(4) . . . . ?
C1 N1 N2 C9 -176.3(3) . . . . ?
C8 N3 N4 C10 -173.6(3) . . . . ?
C7 N1 C1 C6 -167.8(3) . . . . ?
N2 N1 C1 C6 -0.4(4) . . . . ?
C7 N1 C1 C2 13.1(5) . . . . ?
N2 N1 C1 C2 -179.4(3) . . . . ?
C6 C1 C2 C3 1.3(5) . . . . ?
N1 C1 C2 C3 -179.7(3) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C3 C4 C5 C6 0.6(6) . . . . ?
C4 C5 C6 C1 -0.1(5) . . . . ?
C2 C1 C6 C5 -0.8(5) . . . . ?
N1 C1 C6 C5 -179.9(3) . . . . ?
C1 N1 C7 O1 -5.0(6) . . . . ?
N2 N1 C7 O1 -173.2(3) . . . . ?
C1 N1 C7 C8 174.3(3) . . . . ?
N2 N1 C7 C8 6.1(4) . . . . ?
N4 N3 C8 C9 175.1(3) . . . . ?
N4 N3 C8 C7 6.0(6) . . . . ?
O1 C7 C8 N3 -14.0(6) . . . . ?
N1 C7 C8 N3 166.7(4) . . . . ?
O1 C7 C8 C9 175.8(4) . . . . ?
N1 C7 C8 C9 -3.5(4) . . . . ?
N1 N2 C9 O2 -176.5(3) . . . . ?
N1 N2 C9 C8 4.0(4) . . . . ?
N3 C8 C9 O2 8.9(6) . . . . ?
C7 C8 C9 O2 -179.9(4) . . . . ?
N3 C8 C9 N2 -171.6(3) . . . . ?
C7 C8 C9 N2 -0.4(4) . . . . ?
N3 N4 C10 C11 179.6(3) . . . . ?
N3 N4 C10 C15 2.5(5) . . . . ?
C15 C10 C11 C12 2.6(6) . . . . ?
N4 C10 C11 C12 -174.6(3) . . . . ?
C10 C11 C12 C13 0.1(6) . . . . ?
C11 C12 C13 C14 -2.7(6) . . . . ?
C11 C12 C13 Br1 175.1(3) . . . . ?
C12 C13 C14 C15 2.7(6) . . . . ?
Br1 C13 C14 C15 -175.3(3) . . . . ?
C13 C14 C15 C10 0.0(6) . . . . ?
C11 C10 C15 C14 -2.7(6) . . . . ?
N4 C10 C15 C14 174.4(4) . . . . ?

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 H2A O1 0.897(14) 1.99(2) 2.872(4) 167(6) 1_565 yes
N4 H4A O2 0.908(15) 2.56(9) 2.866(4) 101(6) 1_545 yes
C2 H2 O1 0.95 2.30 2.923(5) 123 . yes
C3 H3 Cg2 0.95 2.77 3.452(4) 129 2_565 y
C6 H6 Cg2 0.95 2.88 3.600(4) 134 2_574 y
C11 H11 O2 0.95 2.49 3.363(5) 153 2_565 yes
C12 H12 Cg3 0.95 3.00 3.710(4) 133 2_555 y
C15 H15 Cg3 0.95 2.77 3.402(4) 125 2_564 y
_iucr_geom_hbonds_special_details 
;
Cg2 and Cg3 are , respectively, the centroids of the C1...C6 and 
C10...C15 benzene rings.
;


_refine_diff_density_max         1.215
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.110



loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jtm1543_5
_database_code_depnum_ccdc_archive 'CCDC 2349823'
loop_
_audit_author_name
_audit_author_address
'Joel T Mague'
;South ural state university
Russia
;
_audit_update_record             
;
2024-04-20 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        
(E)-1-phenyl-4-((pyridin-2-ylamino)methylene)pyrazolidine-3,5-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 N4 O2'
_chemical_formula_sum            'C15 H12 N4 O2'
_chemical_formula_weight         280.29

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1973(8)
_cell_length_b                   10.2465(13)
_cell_length_c                   20.461(3)
_cell_angle_alpha                102.548(4)
_cell_angle_beta                 94.531(4)
_cell_angle_gamma                95.302(4)
_cell_volume                     1256.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    8011
_cell_measurement_theta_min      2.490
_cell_measurement_theta_max      28.208

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   0.831
_exptl_transmission_factor_max   0.942
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.058
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Sheldrick, 2009)'
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
The diffraction data were obtained from 8 sets of frames,
each of width 0.5° in ω or φ, collected with scan parameters
determined by the "strategy" routine in APEX4. The scan
time was 20 sec/frame. Analysis of 507 reflections having I/σ(I) 
20 and chosen from the full data set with CELL_NOW 
(Sheldrick, 2008) showed the crystal to belong to the 
triclinic system and to be twinned by a 180° rotation about c*. 
The raw data were processed using the multi-component version of 
SAINT under control of the two-component orientation file 
generated by CELL_NOW.
;
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?
_diffrn_source_power             1.50
_diffrn_source_current           30.0
_diffrn_source_voltage           50
_diffrn_radiation_monochromator  graphite

_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_detector_area_resol_mean 7.3910

_diffrn_reflns_number            6336
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.049
_diffrn_reflns_theta_max         28.512
_diffrn_reflns_theta_full        25.750
_diffrn_measured_fraction_theta_max 0.834
_diffrn_measured_fraction_theta_full 0.890
_diffrn_reflns_Laue_measured_fraction_max 0.834
_diffrn_reflns_Laue_measured_fraction_full 0.890
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_point_group_measured_fraction_full 0.890
_reflns_number_total             6336
_reflns_number_gt                4661
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_cell_refinement       'SAINT (Bruker, 2021)'
_computing_data_reduction        'SAINT (Bruker, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL-2018/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2021)'

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. H-atoms attached to carbon 
were placed in calculated positions (C---H = 0.95 Å) and were 
included as riding contributions with isotropic displacement parameters 
1.2 times those of the attached atoms. Those attached to nitrogen 
were placed in locations derived from a difference map and refined with 
a DFIX 0.91 0.01 instruction. Two reflections affected by the beamstop 
were omitted from the final refinement. Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0577P)²+4.9083P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6336
_refine_ls_number_parameters     392
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0856
_refine_ls_wR_factor_ref         0.2266
_refine_ls_wR_factor_gt          0.2151
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

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
_iucr_geom_hbonds_special_details 
;
Cg3 and Cg5 are the centroids, respectively, of the C1...C6 and the 
C26...C30/N8 rings.
;


_refine_diff_density_max         0.356
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.081



