# Supplementary Information (SI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_24octa_o_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2440016'
loop_
_audit_author_name
_audit_author_address
Srinivas
;IIT Kanpur
India
;
_audit_update_record             
;
2025-04-01 deposited with the CCDC.	2025-06-08 downloaded from the CCDC.
;
_audit_creation_date             2025-02-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C3 H N9 O2), 2(H2 O)'
_chemical_formula_sum            'C6 H6 N18 O6'
_chemical_formula_weight         426.29
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   15.8138(6)
_cell_length_b                   6.4849(3)
_cell_length_c                   16.1635(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.5980(10)
_cell_angle_gamma                90
_cell_volume                     1656.94(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9375
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.297
_cell_measurement_theta_min      2.521
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27013
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.297
_diffrn_reflns_theta_min         2.521
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3444
_reflns_number_total             4123
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4123
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.067
_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)+(0.0457P)²+1.0103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1076
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O6(H6A,H6B), O3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
O4 O 0.44760(8) 0.7290(2) 0.78140(7) 0.0260(3) Uani 1 1 d . . . . .
O1 O 0.68724(8) 0.7443(2) 0.33510(7) 0.0263(3) Uani 1 1 d . . . . .
O2 O 0.72708(7) 0.7013(2) 0.46340(7) 0.0255(3) Uani 1 1 d . . . . .
O5 O 0.31889(7) 0.7505(2) 0.82293(7) 0.0292(3) Uani 1 1 d . . . . .
O6 O 0.62323(8) 0.7459(2) 1.15681(7) 0.0298(3) Uani 1 1 d G . . . .
H6A H 0.676913 0.743872 1.155110 0.045 Uiso 1 1 d G U . . .
H6B H 0.613011 0.759945 1.207817 0.045 Uiso 1 1 d G U . . .
O3 O 0.35565(8) 0.7474(2) 0.62223(7) 0.0299(3) Uani 1 1 d G . . . .
H3A H 0.362766 0.746051 0.674550 0.045 Uiso 1 1 d G U . . .
H3B H 0.302664 0.763568 0.614511 0.045 Uiso 1 1 d G U . . .
N2 N 0.47391(8) 0.76138(19) 0.50747(8) 0.0168(3) Uani 1 1 d . . . . .
H2 H 0.440327 0.758567 0.549965 0.020 Uiso 1 1 calc R U . . .
N10 N 0.51046(8) 0.76101(19) 1.02888(8) 0.0174(3) Uani 1 1 d . . . . .
H10 H 0.556269 0.755704 1.061000 0.021 Uiso 1 1 calc R U . . .
N7 N 0.44543(8) 0.9115(2) 0.27287(8) 0.0201(3) Uani 1 1 d . . . . .
N13 N 0.27144(8) 0.9135(2) 1.06038(8) 0.0206(3) Uani 1 1 d . . . . .
N18 N 0.39562(9) 0.7412(2) 0.83730(8) 0.0202(3) Uani 1 1 d . . . . .
N1 N 0.44618(8) 0.8061(2) 0.42858(8) 0.0179(3) Uani 1 1 d . . . . .
N11 N 0.43164(8) 0.8058(2) 1.05772(8) 0.0178(3) Uani 1 1 d . . . . .
N4 N 0.65747(8) 0.5912(2) 0.60284(8) 0.0206(3) Uani 1 1 d . . . . .
N16 N 0.59181(8) 0.5964(2) 0.84567(8) 0.0200(3) Uani 1 1 d . . . . .
N6 N 0.51442(8) 0.8342(2) 0.29881(8) 0.0209(3) Uani 1 1 d . . . . .
N15 N 0.58916(8) 0.6874(2) 0.91394(8) 0.0199(3) Uani 1 1 d . . . . .
N9 N 0.67162(8) 0.7281(2) 0.40916(8) 0.0194(3) Uani 1 1 d . . . . .
N3 N 0.58876(8) 0.6846(2) 0.59339(8) 0.0196(3) Uani 1 1 d . . . . .
N12 N 0.29406(9) 0.8367(2) 0.99281(8) 0.0220(3) Uani 1 1 d . . . . .
N8 N 0.38827(9) 0.9822(2) 0.24165(9) 0.0263(3) Uani 1 1 d . . . . .
N14 N 0.24232(9) 0.9831(2) 1.11627(9) 0.0265(3) Uani 1 1 d . . . . .
N17 N 0.60762(9) 0.5158(2) 0.78669(9) 0.0268(3) Uani 1 1 d . . . . .
N5 N 0.71658(9) 0.5089(2) 0.62440(9) 0.0280(3) Uani 1 1 d . . . . .
C5 C 0.42673(10) 0.7473(2) 0.91963(9) 0.0172(3) Uani 1 1 d . . . . .
C1 C 0.51486(10) 0.7944(2) 0.38408(9) 0.0177(3) Uani 1 1 d . . . . .
C2 C 0.58704(9) 0.7419(2) 0.43353(9) 0.0166(3) Uani 1 1 d . . . . .
C4 C 0.51092(10) 0.7264(2) 0.94758(9) 0.0166(3) Uani 1 1 d . . . . .
C6 C 0.38117(10) 0.7967(2) 0.99135(9) 0.0175(3) Uani 1 1 d . . . . .
C3 C 0.55670(10) 0.7224(2) 0.51391(9) 0.0165(3) Uani 1 1 d . . . . .


_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
O4 N18 1.2409(18) . ?
O1 N9 1.2334(18) . ?
O2 N9 1.2351(18) . ?
O5 N18 1.2304(18) . ?
O6 H6A 0.8502 . ?
O6 H6B 0.8495 . ?
O3 H3A 0.8500 . ?
O3 H3B 0.8503 . ?
N2 H2 0.8800 . ?
N2 N1 1.3679(18) . ?
N2 C3 1.335(2) . ?
N10 H10 0.8800 . ?
N10 N11 1.3739(18) . ?
N10 C4 1.333(2) . ?
N7 N6 1.2616(19) . ?
N7 N8 1.1210(19) . ?
N13 N12 1.2613(19) . ?
N13 N14 1.1204(19) . ?
N18 C5 1.406(2) . ?
N1 C1 1.321(2) . ?
N11 C6 1.320(2) . ?
N4 N3 1.2498(19) . ?
N4 N5 1.123(2) . ?
N16 N15 1.2533(19) . ?
N16 N17 1.1214(19) . ?
N6 C1 1.402(2) . ?
N15 C4 1.388(2) . ?
N9 C2 1.408(2) . ?
N3 C3 1.390(2) . ?
N12 C6 1.403(2) . ?
C5 C4 1.401(2) . ?
C5 C6 1.419(2) . ?
C1 C2 1.417(2) . ?
C2 C3 1.403(2) . ?

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
H6A O6 H6B 104.5 . . ?
H3A O3 H3B 104.5 . . ?
N1 N2 H2 123.2 . . ?
C3 N2 H2 123.2 . . ?
C3 N2 N1 113.64(12) . . ?
N11 N10 H10 123.2 . . ?
C4 N10 H10 123.2 . . ?
C4 N10 N11 113.57(13) . . ?
N8 N7 N6 172.33(15) . . ?
N14 N13 N12 172.01(16) . . ?
O4 N18 C5 118.00(13) . . ?
O5 N18 O4 122.37(13) . . ?
O5 N18 C5 119.62(14) . . ?
C1 N1 N2 104.38(12) . . ?
C6 N11 N10 104.39(12) . . ?
N5 N4 N3 168.93(16) . . ?
N17 N16 N15 169.03(16) . . ?
N7 N6 C1 112.35(13) . . ?
N16 N15 C4 118.85(13) . . ?
O1 N9 O2 122.91(14) . . ?
O1 N9 C2 118.94(13) . . ?
O2 N9 C2 118.15(13) . . ?
N4 N3 C3 119.48(13) . . ?
N13 N12 C6 112.95(13) . . ?
N18 C5 C6 127.40(14) . . ?
C4 C5 N18 127.36(14) . . ?
C4 C5 C6 104.96(13) . . ?
N1 C1 N6 122.88(14) . . ?
N1 C1 C2 111.60(13) . . ?
N6 C1 C2 125.50(14) . . ?
N9 C2 C1 127.90(14) . . ?
C3 C2 N9 127.26(14) . . ?
C3 C2 C1 104.66(13) . . ?
N10 C4 N15 116.49(13) . . ?
N10 C4 C5 105.69(13) . . ?
N15 C4 C5 137.79(14) . . ?
N11 C6 N12 123.36(14) . . ?
N11 C6 C5 111.39(14) . . ?
N12 C6 C5 125.23(14) . . ?
N2 C3 N3 115.93(13) . . ?
N2 C3 C2 105.71(13) . . ?
N3 C3 C2 138.28(14) . . ?

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
O4 N18 C5 C4 -5.0(2) . . . . ?
O4 N18 C5 C6 168.02(15) . . . . ?
O1 N9 C2 C1 -7.2(2) . . . . ?
O1 N9 C2 C3 178.28(15) . . . . ?
O2 N9 C2 C1 172.45(15) . . . . ?
O2 N9 C2 C3 -2.1(2) . . . . ?
O5 N18 C5 C4 175.92(15) . . . . ?
O5 N18 C5 C6 -11.1(2) . . . . ?
N2 N1 C1 N6 -178.65(14) . . . . ?
N2 N1 C1 C2 0.12(16) . . . . ?
N10 N11 C6 N12 -178.78(14) . . . . ?
N10 N11 C6 C5 -0.25(16) . . . . ?
N7 N6 C1 N1 10.1(2) . . . . ?
N7 N6 C1 C2 -168.50(15) . . . . ?
N13 N12 C6 N11 10.7(2) . . . . ?
N13 N12 C6 C5 -167.65(15) . . . . ?
N18 C5 C4 N10 174.60(14) . . . . ?
N18 C5 C4 N15 -3.2(3) . . . . ?
N18 C5 C6 N11 -174.30(14) . . . . ?
N18 C5 C6 N12 4.2(3) . . . . ?
N1 N2 C3 N3 177.39(12) . . . . ?
N1 N2 C3 C2 -0.10(17) . . . . ?
N1 C1 C2 N9 -175.68(14) . . . . ?
N1 C1 C2 C3 -0.18(17) . . . . ?
N11 N10 C4 N15 177.78(12) . . . . ?
N11 N10 C4 C5 -0.54(17) . . . . ?
N4 N3 C3 N2 159.58(14) . . . . ?
N4 N3 C3 C2 -24.0(3) . . . . ?
N16 N15 C4 N10 159.25(14) . . . . ?
N16 N15 C4 C5 -23.2(3) . . . . ?
N6 C1 C2 N9 3.1(3) . . . . ?
N6 C1 C2 C3 178.55(14) . . . . ?
N9 C2 C3 N2 175.70(14) . . . . ?
N9 C2 C3 N3 -0.9(3) . . . . ?
N17 N16 N15 C4 -175.6(8) . . . . ?
N5 N4 N3 C3 -175.6(8) . . . . ?
C1 C2 C3 N2 0.16(16) . . . . ?
C1 C2 C3 N3 -176.45(18) . . . . ?
C4 N10 N11 C6 0.50(16) . . . . ?
C4 C5 C6 N11 -0.05(17) . . . . ?
C4 C5 C6 N12 178.44(15) . . . . ?
C6 C5 C4 N10 0.34(16) . . . . ?
C6 C5 C4 N15 -177.41(17) . . . . ?
C3 N2 N1 C1 -0.01(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2aprb_a
_database_code_depnum_ccdc_archive 'CCDC 2445030'
loop_
_audit_author_name
_audit_author_address
'Srinivas D'
;IIT Kanpur
India
;
_audit_update_record             
;
2025-04-18 deposited with the CCDC.	2025-06-08 downloaded from the CCDC.
;
_audit_creation_date             2025-04-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H N9 O2'
_chemical_formula_sum            'C3 H N9 O2'
_chemical_formula_weight         195.13
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   14.4561(9)
_cell_length_b                   6.9477(5)
_cell_length_c                   7.1889(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     722.03(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5132
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.18
_cell_measurement_theta_min      2.82
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7169
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0751 before and 0.0486 after correction.
The Ratio of minimum to maximum transmission is 0.9612.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic orangish orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10980
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.225
_diffrn_reflns_theta_min         2.932
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                1833
_reflns_number_total             1949
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 802 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1949
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.146
_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)+(0.0427P)²+0.2018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0910
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
O2 O -0.50602(13) -0.2517(3) -0.1935(3) 0.0244(4) Uani 1 1 d . . . . .
O1 O -0.37518(12) -0.3524(3) -0.3082(3) 0.0262(4) Uani 1 1 d . . . . .
N9 N -0.45475(15) -0.2899(3) -0.3260(3) 0.0187(4) Uani 1 1 d . . . . .
N2 N -0.58670(14) -0.1550(3) -0.7322(3) 0.0196(4) Uani 1 1 d . . . . .
N6 N -0.36847(14) -0.3819(3) -0.7451(3) 0.0232(4) Uani 1 1 d . . . . .
N1 N -0.50858(14) -0.2391(3) -0.8050(3) 0.0178(4) Uani 1 1 d . . . . .
N3 N -0.63845(14) -0.0963(3) -0.4210(3) 0.0225(4) Uani 1 1 d . . . . .
N7 N -0.32081(14) -0.4879(3) -0.6409(3) 0.0226(4) Uani 1 1 d . . . . .
N4 N -0.70739(15) -0.0164(3) -0.4949(3) 0.0238(4) Uani 1 1 d . . . . .
N8 N -0.27054(16) -0.5859(4) -0.5708(4) 0.0326(5) Uani 1 1 d . . . . .
C2 C -0.49053(14) -0.2589(3) -0.5043(4) 0.0165(4) Uani 1 1 d . . . . .
N5 N -0.77272(16) 0.0571(4) -0.5392(3) 0.0339(6) Uani 1 1 d . . . . .
C3 C -0.57540(16) -0.1687(3) -0.5504(3) 0.0178(4) Uani 1 1 d . . . . .
C1 C -0.44883(16) -0.3021(3) -0.6771(3) 0.0169(4) Uani 1 1 d . . . . .
H2 H -0.621(15) -0.07(3) -0.77(4) 0.59(18) Uiso 1 1 d . . . . .


_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
O2 N9 1.236(3) . ?
O1 N9 1.236(3) . ?
N9 C2 1.399(3) . ?
N2 N1 1.375(3) . ?
N2 C3 1.320(3) . ?
N2 H2 0.8(2) . ?
N6 N7 1.256(3) . ?
N6 C1 1.377(3) . ?
N1 C1 1.335(3) . ?
N3 N4 1.259(3) . ?
N3 C3 1.396(3) . ?
N7 N8 1.116(3) . ?
N4 N5 1.119(3) . ?
C2 C3 1.417(3) . ?
C2 C1 1.413(3) . ?

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
O2 N9 O1 123.6(2) . . ?
O2 N9 C2 116.8(2) . . ?
O1 N9 C2 119.54(19) . . ?
N1 N2 H2 133(10) . . ?
C3 N2 N1 104.16(19) . . ?
C3 N2 H2 116(10) . . ?
N7 N6 C1 119.1(2) . . ?
C1 N1 N2 114.1(2) . . ?
N4 N3 C3 113.2(2) . . ?
N8 N7 N6 169.8(3) . . ?
N5 N4 N3 171.5(3) . . ?
N9 C2 C3 127.1(2) . . ?
N9 C2 C1 127.95(19) . . ?
C1 C2 C3 104.9(2) . . ?
N2 C3 N3 123.6(2) . . ?
N2 C3 C2 111.7(2) . . ?
N3 C3 C2 124.6(2) . . ?
N6 C1 C2 139.3(2) . . ?
N1 C1 N6 115.7(2) . . ?
N1 C1 C2 105.1(2) . . ?

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
O2 N9 C2 C3 7.5(3) . . . . ?
O2 N9 C2 C1 -175.6(2) . . . . ?
O1 N9 C2 C3 -172.4(2) . . . . ?
O1 N9 C2 C1 4.6(3) . . . . ?
N9 C2 C3 N2 177.3(2) . . . . ?
N9 C2 C3 N3 -0.6(3) . . . . ?
N9 C2 C1 N6 0.6(4) . . . . ?
N9 C2 C1 N1 -177.8(2) . . . . ?
N2 N1 C1 N6 -178.11(18) . . . . ?
N2 N1 C1 C2 0.7(2) . . . . ?
N1 N2 C3 N3 178.5(2) . . . . ?
N1 N2 C3 C2 0.5(3) . . . . ?
N7 N6 C1 N1 -161.5(2) . . . . ?
N7 N6 C1 C2 20.3(4) . . . . ?
N4 N3 C3 N2 -0.1(3) . . . . ?
N4 N3 C3 C2 177.6(2) . . . . ?
C3 N2 N1 C1 -0.8(3) . . . . ?
C3 C2 C1 N6 178.0(3) . . . . ?
C3 C2 C1 N1 -0.3(2) . . . . ?
C1 N6 N7 N8 176.3(13) . . . . ?
C1 C2 C3 N2 -0.2(2) . . . . ?
C1 C2 C3 N3 -178.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
