# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_mo_2023896_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2g4b21
_database_code_depnum_ccdc_archive 'CCDC 2268272'
loop_
_audit_author_name
_audit_author_address
'Jingwei Meng'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-06-07 deposited with the CCDC.	2023-09-13 downloaded from the CCDC.
;
_audit_creation_date             2023-06-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 N10 O8'
_chemical_formula_sum            'C6 H4 N10 O8'
_chemical_formula_weight         344.19
_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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.899(6)
_cell_length_b                   6.244(2)
_cell_length_c                   30.293(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2440.0(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1496
_cell_measurement_temperature    298
_cell_measurement_theta_max      23.506
_cell_measurement_theta_min      2.689
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1337 before and 0.0676 after correction. The Ratio of minimum to maximum transmission is 0.6637. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0907
_diffrn_reflns_av_unetI/netI     0.0692
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            12044
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.413
_diffrn_reflns_theta_min         2.074
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.976
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1302
_reflns_number_total             2441
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2441
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.1503
_refine_ls_R_factor_gt           0.0803
_refine_ls_restrained_S_all      1.041
_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)+(0.0807P)²+4.4256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1862
_refine_ls_wR_factor_ref         0.2279
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
2. Restrained distances
 N8-N9
 2.2 with sigma of 0.02
 N2-N3 \\sim N7-N8 \\sim C5-N8 \\sim C5-C4 \\sim C6-C4 \\sim N7-C6
 with sigma of 0.02
3. Others
 Fixed Sof: N11(0.6) H11A(0.6) H11B(0.6) N9(0.4) H9A(0.4) H9B(0.4)
4.a Rotating group:
 N1(H1A,H1B), N11(H11A,H11B), N9(H9A,H9B)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_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 0.5148(3) 0.1106(6) 0.67996(11) 0.0683(11) Uani 1 1 d . . . . .
N2 N 0.3583(3) 0.5580(7) 0.70424(12) 0.0552(11) Uani 1 1 d D . . . .
N5 N 0.4622(3) 0.2289(7) 0.70257(13) 0.0571(11) Uani 1 1 d . . . . .
N3 N 0.3398(3) 0.7341(7) 0.68048(14) 0.0628(12) Uani 1 1 d D . . . .
O3 O 0.3416(4) 1.0291(8) 0.61850(16) 0.0979(15) Uani 1 1 d . . . . .
O1 O 0.4445(4) 0.1947(8) 0.74163(12) 0.0952(15) Uani 1 1 d . . . . .
N4 N 0.3989(4) 0.8750(8) 0.61236(15) 0.0680(12) Uani 1 1 d . . . . .
O5 O 0.3273(4) 0.4522(9) 0.56252(16) 0.1032(16) Uani 1 1 d . . . . .
O8 O 0.6573(3) 0.4809(9) 0.68275(17) 0.1032(16) Uani 1 1 d . . . . .
N8 N 0.5861(6) 0.2914(9) 0.54682(18) 0.101(2) Uani 1 1 d D . . . .
O4 O 0.4603(4) 0.8584(7) 0.58207(13) 0.0933(14) Uani 1 1 d . . . . .
N1 N 0.3068(4) 0.5421(8) 0.74465(14) 0.0763(14) Uani 1 1 d . . . . .
H1A H 0.257532 0.449475 0.742047 0.092 Uiso 1 1 d GR . . . .
H1B H 0.348997 0.499641 0.765007 0.092 Uiso 1 1 d GR . . . .
N0AA N 0.3991(6) 0.3565(9) 0.54497(16) 0.0889(18) Uani 1 1 d . . . . .
C1 C 0.4246(3) 0.4209(8) 0.68317(14) 0.0481(11) Uani 1 1 d . . . . .
C2 C 0.4521(3) 0.5140(8) 0.64353(14) 0.0473(11) Uani 1 1 d . . . . .
N6 N 0.6971(4) 0.4324(9) 0.6482(2) 0.0796(15) Uani 1 1 d . . . . .
C4 C 0.5214(4) 0.4284(8) 0.60934(14) 0.0503(12) Uani 1 1 d D . . . .
C3 C 0.3962(4) 0.7039(8) 0.64435(15) 0.0519(12) Uani 1 1 d . . . . .
O7 O 0.7899(3) 0.4165(9) 0.6413(2) 0.123(2) Uani 1 1 d . . . . .
C6 C 0.6279(4) 0.3925(8) 0.61141(17) 0.0640(14) Uani 1 1 d D . . . .
O6 O 0.3934(5) 0.2591(9) 0.51012(13) 0.140(2) Uani 1 1 d . . . . .
N7 N 0.6651(6) 0.3144(9) 0.5738(2) 0.106(2) Uani 1 1 d D . . . .
C5 C 0.4979(5) 0.3627(9) 0.56681(15) 0.0647(15) Uani 1 1 d D . . . .
N11 N 0.6162(9) 0.2150(16) 0.5075(2) 0.105(3) Uani 0.6 1 d . . P A 2
H11A H 0.679465 0.168804 0.510141 0.126 Uiso 0.6 1 d GR . P A 2
H11B H 0.577933 0.107690 0.499101 0.126 Uiso 0.6 1 d GR . P A 2
N9 N 0.7457(11) 0.254(3) 0.5500(6) 0.153(9) Uani 0.4 1 d D . P B 1
H9A H 0.764594 0.117282 0.554243 0.184 Uiso 0.4 1 d GR . P B 1
H9B H 0.738759 0.267630 0.520593 0.184 Uiso 0.4 1 d GR . P B 1


_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 N5 1.215(5) . ?
N2 N3 1.336(6) . ?
N2 N1 1.396(5) . ?
N2 C1 1.369(6) . ?
N5 O1 1.224(5) . ?
N5 C1 1.420(6) . ?
N3 C3 1.328(6) . ?
O3 N4 1.228(6) . ?
N4 O4 1.216(6) . ?
N4 C3 1.443(6) . ?
O5 N0AA 1.224(7) . ?
O8 N6 1.204(6) . ?
N8 N7 1.314(7) . ?
N8 C5 1.363(7) . ?
N8 N11 1.339(8) . ?
N1 H1A 0.8635 . ?
N1 H1B 0.8640 . ?
N0AA O6 1.221(6) . ?
N0AA C5 1.437(8) . ?
C1 C2 1.380(6) . ?
C2 C4 1.469(6) . ?
C2 C3 1.388(7) . ?
N6 O7 1.220(6) . ?
N6 C6 1.449(7) . ?
C4 C6 1.394(7) . ?
C4 C5 1.385(6) . ?
C6 N7 1.329(6) . ?
N7 N9 1.321(13) . ?
N11 H11A 0.8689 . ?
N11 H11B 0.8705 . ?
N9 H9A 0.8967 . ?
N9 H9B 0.8984 . ?

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
N3 N2 N1 116.5(4) . . ?
N3 N2 C1 112.0(4) . . ?
C1 N2 N1 131.4(4) . . ?
O2 N5 O1 122.9(5) . . ?
O2 N5 C1 118.1(4) . . ?
O1 N5 C1 118.9(4) . . ?
C3 N3 N2 103.2(4) . . ?
O3 N4 C3 117.6(5) . . ?
O4 N4 O3 125.0(5) . . ?
O4 N4 C3 117.4(5) . . ?
N7 N8 C5 109.6(5) . . ?
N7 N8 N11 111.5(7) . . ?
N11 N8 C5 138.9(8) . . ?
N2 N1 H1A 108.5 . . ?
N2 N1 H1B 110.4 . . ?
H1A N1 H1B 108.8 . . ?
O5 N0AA C5 117.3(5) . . ?
O6 N0AA O5 125.0(7) . . ?
O6 N0AA C5 117.7(7) . . ?
N2 C1 N5 123.3(4) . . ?
N2 C1 C2 107.6(4) . . ?
C2 C1 N5 128.9(4) . . ?
C1 C2 C4 128.0(4) . . ?
C1 C2 C3 102.2(4) . . ?
C3 C2 C4 129.8(4) . . ?
O8 N6 O7 126.0(6) . . ?
O8 N6 C6 116.7(5) . . ?
O7 N6 C6 117.3(6) . . ?
C6 C4 C2 128.8(4) . . ?
C5 C4 C2 129.1(5) . . ?
C5 C4 C6 102.1(4) . . ?
N3 C3 N4 117.5(5) . . ?
N3 C3 C2 114.9(4) . . ?
C2 C3 N4 127.4(4) . . ?
C4 C6 N6 127.9(5) . . ?
N7 C6 N6 120.1(6) . . ?
N7 C6 C4 112.1(6) . . ?
N8 N7 C6 107.1(6) . . ?
N8 N7 N9 103.9(10) . . ?
N9 N7 C6 149.0(11) . . ?
N8 C5 N0AA 121.8(5) . . ?
N8 C5 C4 109.1(5) . . ?
C4 C5 N0AA 129.0(5) . . ?
N8 N11 H11A 108.1 . . ?
N8 N11 H11B 111.7 . . ?
H11A N11 H11B 107.7 . . ?
N7 N9 H9A 114.1 . . ?
N7 N9 H9B 115.8 . . ?
H9A N9 H9B 105.1 . . ?

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
O2 N5 C1 N2 174.8(4) . . . . ?
O2 N5 C1 C2 -11.4(7) . . . . ?
N2 N3 C3 N4 -176.0(4) . . . . ?
N2 N3 C3 C2 -0.4(5) . . . . ?
N2 C1 C2 C4 -179.8(4) . . . . ?
N2 C1 C2 C3 -0.9(5) . . . . ?
N5 C1 C2 C4 5.6(8) . . . . ?
N5 C1 C2 C3 -175.5(4) . . . . ?
N3 N2 C1 N5 175.7(4) . . . . ?
N3 N2 C1 C2 0.7(5) . . . . ?
O3 N4 C3 N3 -6.6(7) . . . . ?
O3 N4 C3 C2 178.5(5) . . . . ?
O1 N5 C1 N2 -8.6(7) . . . . ?
O1 N5 C1 C2 165.2(5) . . . . ?
O5 N0AA C5 N8 -169.4(6) . . . . ?
O5 N0AA C5 C4 13.2(9) . . . . ?
O8 N6 C6 C4 8.6(9) . . . . ?
O8 N6 C6 N7 -172.2(6) . . . . ?
O4 N4 C3 N3 171.1(5) . . . . ?
O4 N4 C3 C2 -3.8(8) . . . . ?
N1 N2 N3 C3 -178.9(4) . . . . ?
N1 N2 C1 N5 -5.8(8) . . . . ?
N1 N2 C1 C2 179.2(5) . . . . ?
C1 N2 N3 C3 -0.2(5) . . . . ?
C1 C2 C4 C6 -67.0(8) . . . . ?
C1 C2 C4 C5 113.1(6) . . . . ?
C1 C2 C3 N3 0.9(6) . . . . ?
C1 C2 C3 N4 175.9(5) . . . . ?
C2 C4 C6 N6 -0.3(9) . . . . ?
C2 C4 C6 N7 -179.6(5) . . . . ?
C2 C4 C5 N8 -179.1(5) . . . . ?
C2 C4 C5 N0AA -1.4(9) . . . . ?
N6 C6 N7 N8 179.1(5) . . . . ?
N6 C6 N7 N9 -4(2) . . . . ?
C4 C2 C3 N3 179.7(5) . . . . ?
C4 C2 C3 N4 -5.2(8) . . . . ?
C4 C6 N7 N8 -1.6(7) . . . . ?
C4 C6 N7 N9 175.1(17) . . . . ?
C3 C2 C4 C6 114.4(6) . . . . ?
C3 C2 C4 C5 -65.5(8) . . . . ?
O7 N6 C6 C4 -170.5(5) . . . . ?
O7 N6 C6 N7 8.7(8) . . . . ?
C6 C4 C5 N8 1.0(6) . . . . ?
C6 C4 C5 N0AA 178.6(5) . . . . ?
O6 N0AA C5 N8 9.6(8) . . . . ?
O6 N0AA C5 C4 -167.8(6) . . . . ?
N7 N8 C5 N0AA -179.9(5) . . . . ?
N7 N8 C5 C4 -2.0(7) . . . . ?
C5 N8 N7 C6 2.2(7) . . . . ?
C5 N8 N7 N9 -176.0(9) . . . . ?
C5 C4 C6 N6 179.6(5) . . . . ?
C5 C4 C6 N7 0.4(6) . . . . ?
N11 N8 N7 C6 179.4(6) . . . . ?
N11 N8 C5 N0AA 4.2(12) . . . . ?
N11 N8 C5 C4 -178.0(9) . . . . ?

_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_mm
_database_code_depnum_ccdc_archive 'CCDC 2206102'
loop_
_audit_author_name
_audit_author_address
'M JW'
;BIT
China
;
_audit_update_record             
;
2022-09-08 deposited with the CCDC.	2023-09-13 downloaded from the CCDC.
;
_audit_creation_date             2021-12-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 N10 O8'
_chemical_formula_sum            'C6 H4 N10 O8'
_chemical_formula_weight         344.19
_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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.8197(17)
_cell_length_b                   6.1427(7)
_cell_length_c                   30.168(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2375.7(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1429
_cell_measurement_temperature    170
_cell_measurement_theta_max      20.678
_cell_measurement_theta_min      2.700
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0911 before and 0.0674 after correction. The Ratio of minimum to maximum transmission is 0.9238. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.925
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0979
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            12006
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.353
_diffrn_reflns_theta_min         2.085
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1217
_reflns_number_total             2111
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2111
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.1506
_refine_ls_R_factor_gt           0.0849
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0791P)²+10.0437P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1959
_refine_ls_wR_factor_ref         0.2358
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
2. Restrained distances
 N8-N7
 1.45 with sigma of 0.02
 N3-H3B = N3-H3A
 0.87 with sigma of 0.02
 N8-N7 \\sim N10-N9 \\sim N3-N2
 with sigma of 0.02
 N7-N9 \\sim N4-N2
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N9) \\sim Ueq, Uanis(N7) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(N10) \\sim Ueq, Uanis(N8) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4. Others
 Fixed Sof: N10(0.65) H10A(0.65) H10B(0.65) N8(0.35) H8A(0.35) H8B(0.35)
5.a Rotating group:
 N10(H10A,H10B), N8(H8A,H8B)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_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
O13 O 0.5163(3) 0.1062(7) 0.32030(14) 0.0493(12) Uani 1 1 d . . . . .
N2 N 0.3581(4) 0.5587(9) 0.29511(15) 0.0407(12) Uani 1 1 d D . . . .
O12 O 0.4445(4) 0.1903(8) 0.25759(14) 0.0659(15) Uani 1 1 d . . . . .
N1 N 0.4628(4) 0.2245(8) 0.29697(16) 0.0416(12) Uani 1 1 d . . . . .
O15 O 0.4569(5) 0.8626(8) 0.41844(17) 0.0677(15) Uani 1 1 d . . . . .
O14 O 0.3399(4) 1.0401(8) 0.38071(18) 0.0684(15) Uani 1 1 d . . . . .
N4 N 0.3389(4) 0.7355(9) 0.31869(17) 0.0458(13) Uani 1 1 d D . . . .
N5 N 0.3964(5) 0.8805(9) 0.38748(19) 0.0507(14) Uani 1 1 d . . . . .
O16 O 0.6571(4) 0.4755(10) 0.3174(2) 0.0752(17) Uani 1 1 d . . . . .
O18 O 0.3258(5) 0.4597(10) 0.4379(2) 0.0815(18) Uani 1 1 d . . . . .
N3 N 0.3066(5) 0.5400(11) 0.25455(19) 0.0562(16) Uani 1 1 d D . . . .
N6 N 0.6963(5) 0.4281(10) 0.3520(3) 0.0616(18) Uani 1 1 d . . . . .
C1 C 0.4244(4) 0.4206(9) 0.31654(18) 0.0336(13) Uani 1 1 d . . . . .
C4 C 0.5196(5) 0.4287(9) 0.39103(18) 0.0377(14) Uani 1 1 d . . . . .
C2 C 0.4507(5) 0.5128(9) 0.35648(18) 0.0360(14) Uani 1 1 d . . . . .
N11 N 0.3961(8) 0.3590(11) 0.4551(2) 0.078(2) Uani 1 1 d . . . . .
C3 C 0.3949(5) 0.7076(10) 0.35534(19) 0.0397(14) Uani 1 1 d . . . . .
O17 O 0.7893(4) 0.4103(10) 0.3598(2) 0.100(2) Uani 1 1 d . . . . .
N9 N 0.5876(6) 0.2918(10) 0.4529(2) 0.0692(18) Uani 1 1 d D U . . .
C6 C 0.4959(6) 0.3643(10) 0.4338(2) 0.0505(17) Uani 1 1 d . . . . .
O19 O 0.3905(7) 0.2573(10) 0.49002(17) 0.121(3) Uani 1 1 d . . . . .
C5 C 0.6271(6) 0.3895(10) 0.3890(2) 0.0518(18) Uani 1 1 d . . . . .
N7 N 0.6649(6) 0.3117(11) 0.4266(2) 0.080(2) Uani 1 1 d D U . . .
N10 N 0.6147(10) 0.2177(19) 0.4938(3) 0.090(3) Uani 0.65 1 d D U P A 1
H10A H 0.580217 0.096511 0.500503 0.108 Uiso 0.65 1 d GR . P A 1
H10B H 0.682470 0.187087 0.493566 0.108 Uiso 0.65 1 d GR . P A 1
N8 N 0.7399(14) 0.241(3) 0.4551(6) 0.074(5) Uani 0.35 1 d D U P B 2
H8A H 0.709710 0.157352 0.475176 0.089 Uiso 0.35 1 d GR . P B 2
H8B H 0.788072 0.164963 0.440997 0.089 Uiso 0.35 1 d GR . P B 2
H3A H 0.273(6) 0.416(8) 0.255(3) 0.09(3) Uiso 1 1 d D . . . .
H3B H 0.354(5) 0.508(14) 0.234(2) 0.09(3) Uiso 1 1 d 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
O13 N1 1.222(6) . ?
N2 N4 1.321(7) . ?
N2 N3 1.395(7) . ?
N2 C1 1.364(7) . ?
O12 N1 1.229(6) . ?
N1 C1 1.428(7) . ?
O15 N5 1.219(7) . ?
O14 N5 1.236(7) . ?
N4 C3 1.329(7) . ?
N5 C3 1.438(8) . ?
O16 N6 1.194(8) . ?
O18 N11 1.211(9) . ?
N6 O17 1.220(7) . ?
N6 C5 1.445(9) . ?
C1 C2 1.373(8) . ?
C4 C2 1.460(8) . ?
C4 C6 1.383(8) . ?
C4 C5 1.401(9) . ?
C2 C3 1.395(8) . ?
N11 C6 1.432(10) . ?
N11 O19 1.227(8) . ?
N9 C6 1.384(9) . ?
N9 N7 1.274(9) . ?
N9 N10 1.359(9) . ?
C5 N7 1.322(9) . ?
N7 N8 1.360(11) . ?

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
N4 N2 N3 116.8(5) . . ?
N4 N2 C1 111.8(5) . . ?
C1 N2 N3 131.3(5) . . ?
O13 N1 O12 124.2(5) . . ?
O13 N1 C1 117.2(5) . . ?
O12 N1 C1 118.6(5) . . ?
N2 N4 C3 103.9(5) . . ?
O15 N5 O14 124.8(6) . . ?
O15 N5 C3 117.3(6) . . ?
O14 N5 C3 117.8(6) . . ?
O16 N6 O17 126.9(8) . . ?
O16 N6 C5 117.2(6) . . ?
O17 N6 C5 115.9(8) . . ?
N2 C1 N1 122.9(5) . . ?
N2 C1 C2 108.2(5) . . ?
C2 C1 N1 128.7(5) . . ?
C6 C4 C2 129.4(6) . . ?
C6 C4 C5 102.0(6) . . ?
C5 C4 C2 128.7(6) . . ?
C1 C2 C4 129.0(5) . . ?
C1 C2 C3 101.9(5) . . ?
C3 C2 C4 129.1(5) . . ?
O18 N11 C6 117.5(6) . . ?
O18 N11 O19 125.8(9) . . ?
O19 N11 C6 116.7(9) . . ?
N4 C3 N5 118.2(5) . . ?
N4 C3 C2 114.1(5) . . ?
C2 C3 N5 127.6(6) . . ?
N7 N9 C6 111.7(6) . . ?
N7 N9 N10 113.4(8) . . ?
N10 N9 C6 134.7(9) . . ?
C4 C6 N11 128.4(7) . . ?
C4 C6 N9 107.1(6) . . ?
N9 C6 N11 124.4(6) . . ?
C4 C5 N6 127.5(6) . . ?
N7 C5 N6 119.8(7) . . ?
N7 C5 C4 112.6(7) . . ?
N9 N7 C5 106.5(7) . . ?
N9 N7 N8 97.2(11) . . ?
C5 N7 N8 156.2(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
