# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 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_mo_2023683_0m_sq
_database_code_depnum_ccdc_archive 'CCDC 2303258'
loop_
_audit_author_name
_audit_author_address
ZT
;Nanjing university of science and technology
China
;
_audit_update_record             
;
2023-10-24 deposited with the CCDC.	2024-01-15 downloaded from the CCDC.
;
_audit_creation_date             2023-05-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H3 N9 O4'
_chemical_formula_sum            'C8 H3 N9 O4'
_chemical_formula_weight         289.19
_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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   23.212(3)
_cell_length_b                   23.212(3)
_cell_length_c                   11.2896(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5267.8(15)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    2104
_cell_measurement_temperature    170
_cell_measurement_theta_max      24.043
_cell_measurement_theta_min      3.040
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1402 before and 0.0816 after correction.
The Ratio of minimum to maximum transmission is 0.7214.
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    1.641
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2628
_exptl_crystal_size_max          0.11
_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  0.0889
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10264
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.355
_diffrn_reflns_theta_min         2.069
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1491
_reflns_number_total             2389
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2389
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.063
_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)+(0.0610P)²+6.9776P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1601
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N7-H7 = N3-H3
 0.87 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8)
;
_atom_sites_solution_hydrogens   mixed
_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
O4 O 0.64178(11) 0.76838(11) 0.2360(2) 0.0419(6) Uani 1 1 d . . . . .
O2 O 0.59921(12) 0.84776(11) 0.7283(2) 0.0456(6) Uani 1 1 d . . . . .
O1 O 0.43599(11) 0.73406(12) 0.5431(2) 0.0475(6) Uani 1 1 d . . . . .
O3 O 0.54467(13) 0.82722(13) 0.8938(2) 0.0532(7) Uani 1 1 d . . . . .
N4 N 0.59297(12) 0.74904(12) 0.5426(2) 0.0298(6) Uani 1 1 d . . . . .
N7 N 0.58520(13) 0.68194(13) 0.9327(3) 0.0362(7) Uani 1 1 d D . . . .
N5 N 0.68162(13) 0.75084(12) 0.4691(2) 0.0351(6) Uani 1 1 d . . . . .
N9 N 0.57477(13) 0.81482(13) 0.8183(2) 0.0375(7) Uani 1 1 d . . . . .
N6 N 0.68154(13) 0.74291(13) 0.5908(2) 0.0356(6) Uani 1 1 d . . . . .
N8 N 0.57003(13) 0.73088(13) 0.9439(2) 0.0372(7) Uani 1 1 d . . . . .
N1 N 0.48803(13) 0.73717(13) 0.6100(2) 0.0386(7) Uani 1 1 d . . . . .
N3 N 0.54603(14) 0.75597(14) 0.3153(2) 0.0388(7) Uani 1 1 d D . . . .
N2 N 0.45011(14) 0.74089(14) 0.4220(2) 0.0449(7) Uani 1 1 d . . . . .
C5 C 0.62794(15) 0.74155(15) 0.6341(3) 0.0311(7) Uani 1 1 d . . . . .
C6 C 0.60721(14) 0.72829(15) 0.7570(3) 0.0318(7) Uani 1 1 d . . . . .
C4 C 0.62811(15) 0.75366(14) 0.4424(3) 0.0324(7) Uani 1 1 d . . . . .
C7 C 0.58347(15) 0.75832(15) 0.8374(3) 0.0327(7) Uani 1 1 d . . . . .
C1 C 0.53142(15) 0.74490(15) 0.5303(3) 0.0318(7) Uani 1 1 d . . . . .
C2 C 0.50959(16) 0.74794(15) 0.4149(3) 0.0344(7) Uani 1 1 d . . . . .
C8 C 0.60727(15) 0.67895(15) 0.8245(3) 0.0334(7) Uani 1 1 d . . . . .
H8 H 0.620545 0.648320 0.799020 0.040 Uiso 1 1 calc R U . . .
C3 C 0.60676(16) 0.75983(15) 0.3222(3) 0.0343(7) Uani 1 1 d . . . . .
H3 H 0.5317(17) 0.7561(18) 0.241(2) 0.058(11) Uiso 1 1 d D . . . .
H7 H 0.5804(18) 0.6562(16) 0.994(2) 0.056(11) 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
O4 C3 1.219(4) . ?
O2 N9 1.227(3) . ?
O1 N1 1.396(3) . ?
O1 N2 1.397(3) . ?
O3 N9 1.224(3) . ?
N4 C5 1.377(4) . ?
N4 C4 1.367(4) . ?
N4 C1 1.390(4) . ?
N7 N8 1.353(4) . ?
N7 C8 1.340(4) . ?
N7 H7 0.884(18) . ?
N5 N6 1.386(4) . ?
N5 C4 1.311(4) . ?
N9 C7 1.440(4) . ?
N6 C5 1.322(4) . ?
N8 C7 1.322(4) . ?
N1 C1 1.294(4) . ?
N3 C2 1.363(4) . ?
N3 C3 1.369(4) . ?
N3 H3 0.899(18) . ?
N2 C2 1.309(4) . ?
C5 C6 1.451(4) . ?
C6 C7 1.413(4) . ?
C6 C8 1.376(4) . ?
C4 C3 1.475(4) . ?
C1 C2 1.412(4) . ?
C8 H8 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
N1 O1 N2 112.1(2) . . ?
C5 N4 C1 135.7(3) . . ?
C4 N4 C5 105.3(2) . . ?
C4 N4 C1 118.4(2) . . ?
N8 N7 H7 120(2) . . ?
C8 N7 N8 113.3(3) . . ?
C8 N7 H7 127(2) . . ?
C4 N5 N6 107.2(2) . . ?
O2 N9 C7 117.4(3) . . ?
O3 N9 O2 124.8(3) . . ?
O3 N9 C7 117.8(3) . . ?
C5 N6 N5 107.9(2) . . ?
C7 N8 N7 102.8(2) . . ?
C1 N1 O1 103.0(2) . . ?
C2 N3 C3 120.7(3) . . ?
C2 N3 H3 124(2) . . ?
C3 N3 H3 115(2) . . ?
C2 N2 O1 104.3(2) . . ?
N4 C5 C6 126.2(3) . . ?
N6 C5 N4 109.1(3) . . ?
N6 C5 C6 124.5(3) . . ?
C7 C6 C5 132.8(3) . . ?
C8 C6 C5 124.6(3) . . ?
C8 C6 C7 102.6(3) . . ?
N4 C4 C3 123.5(3) . . ?
N5 C4 N4 110.4(3) . . ?
N5 C4 C3 126.1(3) . . ?
N8 C7 N9 117.9(3) . . ?
N8 C7 C6 113.7(3) . . ?
C6 C7 N9 128.3(3) . . ?
N4 C1 C2 118.0(3) . . ?
N1 C1 N4 129.9(3) . . ?
N1 C1 C2 112.0(3) . . ?
N3 C2 C1 123.7(3) . . ?
N2 C2 N3 127.7(3) . . ?
N2 C2 C1 108.7(3) . . ?
N7 C8 C6 107.6(3) . . ?
N7 C8 H8 126.2 . . ?
C6 C8 H8 126.2 . . ?
O4 C3 N3 123.1(3) . . ?
O4 C3 C4 121.4(3) . . ?
N3 C3 C4 115.5(3) . . ?

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 C7 N8 166.1(3) . . . . ?
O2 N9 C7 C6 -11.5(5) . . . . ?
O1 N1 C1 N4 -177.7(3) . . . . ?
O1 N1 C1 C2 1.0(3) . . . . ?
O1 N2 C2 N3 179.6(3) . . . . ?
O1 N2 C2 C1 0.5(3) . . . . ?
O3 N9 C7 N8 -12.6(4) . . . . ?
O3 N9 C7 C6 169.8(3) . . . . ?
N4 C5 C6 C7 -49.9(5) . . . . ?
N4 C5 C6 C8 130.4(3) . . . . ?
N4 C4 C3 O4 174.9(3) . . . . ?
N4 C4 C3 N3 -4.4(4) . . . . ?
N4 C1 C2 N3 -1.3(5) . . . . ?
N4 C1 C2 N2 177.8(3) . . . . ?
N7 N8 C7 N9 -178.1(2) . . . . ?
N7 N8 C7 C6 -0.1(3) . . . . ?
N5 N6 C5 N4 -0.5(3) . . . . ?
N5 N6 C5 C6 174.5(3) . . . . ?
N5 C4 C3 O4 -6.1(5) . . . . ?
N5 C4 C3 N3 174.5(3) . . . . ?
N6 N5 C4 N4 1.1(3) . . . . ?
N6 N5 C4 C3 -178.0(3) . . . . ?
N6 C5 C6 C7 136.0(3) . . . . ?
N6 C5 C6 C8 -43.7(5) . . . . ?
N8 N7 C8 C6 -0.2(4) . . . . ?
N1 O1 N2 C2 0.1(3) . . . . ?
N1 C1 C2 N3 179.9(3) . . . . ?
N1 C1 C2 N2 -1.0(4) . . . . ?
N2 O1 N1 C1 -0.7(3) . . . . ?
C5 N4 C4 N5 -1.3(3) . . . . ?
C5 N4 C4 C3 177.8(3) . . . . ?
C5 N4 C1 N1 6.5(6) . . . . ?
C5 N4 C1 C2 -172.0(3) . . . . ?
C5 C6 C7 N9 -2.0(5) . . . . ?
C5 C6 C7 N8 -179.8(3) . . . . ?
C5 C6 C8 N7 179.9(3) . . . . ?
C4 N4 C5 N6 1.1(3) . . . . ?
C4 N4 C5 C6 -173.8(3) . . . . ?
C4 N4 C1 N1 176.5(3) . . . . ?
C4 N4 C1 C2 -2.1(4) . . . . ?
C4 N5 N6 C5 -0.3(3) . . . . ?
C7 C6 C8 N7 0.1(3) . . . . ?
C1 N4 C5 N6 172.0(3) . . . . ?
C1 N4 C5 C6 -2.9(5) . . . . ?
C1 N4 C4 N5 -174.1(2) . . . . ?
C1 N4 C4 C3 5.0(4) . . . . ?
C2 N3 C3 O4 -178.4(3) . . . . ?
C2 N3 C3 C4 0.9(4) . . . . ?
C8 N7 N8 C7 0.2(3) . . . . ?
C8 C6 C7 N9 177.7(3) . . . . ?
C8 C6 C7 N8 0.0(3) . . . . ?
C3 N3 C2 N2 -177.1(3) . . . . ?
C3 N3 C2 C1 1.8(5) . . . . ?

loop_
_platon_missing_refln_index_h
_platon_missing_refln_index_k
_platon_missing_refln_index_l
_platon_missing_refln_theta
-1 2 0 1.755
0 6 0 6.089

_platon_squeeze_details          
;
TITL mo_2023683_0m_a.res in R-3
CELL   23.2120   23.2120   11.2896     90.00     90.00    120.00
SPGR R-3
# Solvent Accessible Volume =       569
# Electrons Found in S.A.V. =       210
# Note: Atoms in Void are Labelled as Cxxx and Qxxx for all Others
C101 0.478 0.753 0.106 !       9.20 eA-3
C102 1.000 1.001 0.438 !       2.19 eA-3
Q103 0.798 0.915 0.436 !       0.76 eA-3
Q104 0.976 0.615 0.205 !       0.73 eA-3
Q105 0.719 0.224 0.954 !       0.66 eA-3
Q106 0.077 0.156 0.448 !       0.61 eA-3
Q107 0.559 0.155 0.826 !       0.59 eA-3
Q108 0.624 0.273 0.880 !       0.58 eA-3
Q109 0.922 0.995 0.531 !       0.57 eA-3
Q110 0.271 0.242 0.690 !       0.55 eA-3
Q111 0.258 0.700 0.219 !       0.54 eA-3
Q112 0.132 0.025 0.475 !       0.54 eA-3
Q113 0.739 0.750 0.345 !       0.53 eA-3
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.333 0.667 0.167 189 70 ' '
2 0.000 0.000 0.500 191 70 ' '
3 0.667 0.333 0.833 189 70 ' '

_platon_squeeze_void_probe_radius 1.20

_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_221003li_gongsi_nlg_zt113_0m
_database_code_depnum_ccdc_archive 'CCDC 2303260'
loop_
_audit_author_name
_audit_author_address
ZT
;Nanjing university of science and technology
China
;
_audit_update_record             
;
2023-10-24 deposited with the CCDC.	2024-01-15 downloaded from the CCDC.
;
_audit_creation_date             2022-10-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H4 N14 O5, C H4 O'
_chemical_formula_sum            'C13 H8 N14 O6'
_chemical_formula_weight         456.33
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2696(8)
_cell_length_b                   10.8752(12)
_cell_length_c                   12.1046(14)
_cell_angle_alpha                93.652(5)
_cell_angle_beta                 102.562(6)
_cell_angle_gamma                103.331(5)
_cell_volume                     902.34(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4270
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      53.752
_cell_measurement_theta_min      3.278
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.921
_exptl_absorpt_coefficient_mu    0.764
_exptl_absorpt_correction_T_max  0.8636
_exptl_absorpt_correction_T_min  0.5859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1503 before and 0.0855 after correction.
The Ratio of minimum to maximum transmission is 0.6784.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0859
_diffrn_reflns_av_unetI/netI     0.0909
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.985
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8244
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.951
_diffrn_reflns_theta_min         3.278
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2385
_reflns_number_total             3249
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3249
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0872
_refine_ls_restrained_S_all      1.070
_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)+(0.1406P)²+0.8622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2279
_refine_ls_wR_factor_ref         0.2455
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N9-H9
 0.88 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), N12(H12)
3.b Idealised Me refined as rotating group:
 C13(H13B,H13A,H13C)
3.c Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.6101(5) 0.3682(3) 0.3892(3) 0.0284(8) Uani 1 1 d . . . . .
N1 N 0.6402(5) 0.4147(3) 0.4945(3) 0.0363(8) Uani 1 1 d . . . . .
O1 O 0.7835(4) 0.5274(2) 0.5051(2) 0.0390(7) Uani 1 1 d . . . . .
C2 C 0.7328(5) 0.4497(3) 0.3330(3) 0.0291(8) Uani 1 1 d . . . . .
N2 N 0.8404(5) 0.5485(3) 0.4034(3) 0.0356(8) Uani 1 1 d . . . . .
O2 O -0.1874(4) 0.1550(3) 0.4820(3) 0.0549(9) Uani 1 1 d . . . . .
C3 C 0.5939(6) 0.3112(3) 0.1575(3) 0.0346(9) Uani 1 1 d . . . . .
N3 N 0.4793(4) 0.2576(3) 0.3283(2) 0.0275(7) Uani 1 1 d . . . . .
O3 O -0.0441(5) 0.2164(3) 0.3480(3) 0.0505(8) Uani 1 1 d . . . . .
C4 C 0.4691(6) 0.2276(3) 0.2154(3) 0.0331(9) Uani 1 1 d . . . . .
N4 N 0.2561(5) 0.0796(3) 0.2638(3) 0.0394(9) Uani 1 1 d . . . . .
O4 O 1.4597(5) 0.5910(4) 0.2271(3) 0.0667(11) Uani 1 1 d . . . . .
C5 C 0.3413(5) 0.1616(3) 0.3551(3) 0.0311(9) Uani 1 1 d . . . . .
N5 N 0.3363(5) 0.1219(3) 0.1741(3) 0.0420(9) Uani 1 1 d . . . . .
O5 O 1.2081(6) 0.4349(3) 0.2100(4) 0.0720(12) Uani 1 1 d . . . . .
C6 C 0.3030(6) 0.1529(3) 0.4680(3) 0.0315(9) Uani 1 1 d . . . . .
N6 N 0.7250(4) 0.4187(3) 0.2191(3) 0.0306(7) Uani 1 1 d . . . . .
C7 C 0.4302(6) 0.1363(4) 0.5654(3) 0.0389(10) Uani 1 1 d . . . . .
H7 H 0.561766 0.133268 0.572720 0.047 Uiso 1 1 calc R U . . .
N7 N 0.7414(6) 0.4103(3) 0.0398(3) 0.0471(10) Uani 1 1 d . . . . .
C8 C 0.1327(5) 0.1520(3) 0.5048(3) 0.0319(9) Uani 1 1 d . . . . .
N8 N 0.6018(6) 0.3028(3) 0.0516(3) 0.0469(10) Uani 1 1 d . . . . .
C9 C 0.8139(6) 0.4782(4) 0.1396(3) 0.0354(9) Uani 1 1 d . . . . .
N9 N 0.3322(5) 0.1254(3) 0.6474(3) 0.0389(8) Uani 1 1 d D . . . .
H9 H 0.375(6) 0.122(4) 0.7234(18) 0.035(11) Uiso 1 1 d D . . . .
C10 C 0.9558(6) 0.6012(4) 0.1666(3) 0.0336(9) Uani 1 1 d . . . . .
N10 N 0.1485(5) 0.1343(3) 0.6122(3) 0.0364(8) Uani 1 1 d . . . . .
C11 C 0.9141(6) 0.7178(4) 0.1682(4) 0.0423(10) Uani 1 1 d . . . . .
H11 H 0.788091 0.733189 0.151216 0.051 Uiso 1 1 calc R U . . .
N11 N -0.0456(5) 0.1752(3) 0.4406(3) 0.0392(8) Uani 1 1 d . . . . .
C12 C 1.1591(6) 0.6333(4) 0.1980(3) 0.0344(9) Uani 1 1 d . . . . .
N12 N 1.0856(5) 0.8069(3) 0.1985(3) 0.0407(9) Uani 1 1 d . . . . .
H12 H 1.095048 0.889310 0.205178 0.049 Uiso 1 1 calc R U . . .
N13 N 1.2394(5) 0.7567(3) 0.2172(3) 0.0387(8) Uani 1 1 d . . . . .
N14 N 1.2851(6) 0.5475(4) 0.2121(3) 0.0476(10) Uani 1 1 d . . . . .
O6 O 0.6153(5) -0.0957(3) 0.1297(3) 0.0610(10) Uani 1 1 d . . . . .
H6 H 0.544454 -0.144351 0.071934 0.092 Uiso 1 1 calc R U . . .
C13 C 0.7552(10) 0.0037(6) 0.0950(5) 0.0752(18) Uani 1 1 d . . . . .
H13B H 0.843537 -0.034493 0.061763 0.113 Uiso 1 1 calc R U . . .
H13A H 0.830399 0.064610 0.161536 0.113 Uiso 1 1 calc R U . . .
H13C H 0.685894 0.047883 0.038183 0.113 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
C1 N1 1.294(5) . ?
C1 C2 1.421(5) . ?
C1 N3 1.396(4) . ?
N1 O1 1.392(4) . ?
O1 N2 1.398(4) . ?
C2 N2 1.303(5) . ?
C2 N6 1.385(5) . ?
O2 N11 1.224(5) . ?
C3 C4 1.455(5) . ?
C3 N6 1.377(5) . ?
C3 N8 1.293(5) . ?
N3 C4 1.367(5) . ?
N3 C5 1.379(5) . ?
O3 N11 1.235(5) . ?
C4 N5 1.307(5) . ?
N4 C5 1.312(5) . ?
N4 N5 1.396(5) . ?
O4 N14 1.216(5) . ?
C5 C6 1.458(5) . ?
O5 N14 1.219(5) . ?
C6 C7 1.381(6) . ?
C6 C8 1.402(6) . ?
N6 C9 1.386(5) . ?
C7 H7 0.9500 . ?
C7 N9 1.339(5) . ?
N7 N8 1.398(5) . ?
N7 C9 1.309(5) . ?
C8 N10 1.310(5) . ?
C8 N11 1.445(5) . ?
C9 C10 1.457(5) . ?
N9 H9 0.911(19) . ?
N9 N10 1.338(5) . ?
C10 C11 1.370(6) . ?
C10 C12 1.397(6) . ?
C11 H11 0.9500 . ?
C11 N12 1.352(5) . ?
C12 N13 1.318(5) . ?
C12 N14 1.444(6) . ?
N12 H12 0.8800 . ?
N12 N13 1.336(5) . ?
O6 H6 0.8400 . ?
O6 C13 1.455(7) . ?
C13 H13B 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13C 0.9800 . ?

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
N1 C1 C2 110.3(3) . . ?
N1 C1 N3 130.1(3) . . ?
N3 C1 C2 119.6(3) . . ?
C1 N1 O1 103.8(3) . . ?
N1 O1 N2 112.5(3) . . ?
N2 C2 C1 110.2(3) . . ?
N2 C2 N6 129.5(3) . . ?
N6 C2 C1 120.3(3) . . ?
C2 N2 O1 103.2(3) . . ?
N6 C3 C4 118.9(3) . . ?
N8 C3 C4 129.8(3) . . ?
N8 C3 N6 111.3(3) . . ?
C4 N3 C1 120.3(3) . . ?
C4 N3 C5 105.3(3) . . ?
C5 N3 C1 134.3(3) . . ?
N3 C4 C3 120.2(3) . . ?
N5 C4 C3 129.1(4) . . ?
N5 C4 N3 110.7(3) . . ?
C5 N4 N5 108.4(3) . . ?
N3 C5 C6 124.7(3) . . ?
N4 C5 N3 108.9(3) . . ?
N4 C5 C6 126.4(3) . . ?
C4 N5 N4 106.6(3) . . ?
C7 C6 C5 126.5(4) . . ?
C7 C6 C8 102.9(3) . . ?
C8 C6 C5 130.4(4) . . ?
C2 N6 C9 134.7(3) . . ?
C3 N6 C2 120.7(3) . . ?
C3 N6 C9 104.4(3) . . ?
C6 C7 H7 126.6 . . ?
N9 C7 C6 106.7(4) . . ?
N9 C7 H7 126.6 . . ?
C9 N7 N8 108.4(3) . . ?
C6 C8 N11 127.5(3) . . ?
N10 C8 C6 113.4(3) . . ?
N10 C8 N11 119.0(4) . . ?
C3 N8 N7 106.7(3) . . ?
N6 C9 C10 123.1(3) . . ?
N7 C9 N6 109.2(3) . . ?
N7 C9 C10 127.6(4) . . ?
C7 N9 H9 130(3) . . ?
N10 N9 C7 113.3(3) . . ?
N10 N9 H9 116(3) . . ?
C11 C10 C9 125.9(4) . . ?
C11 C10 C12 102.6(3) . . ?
C12 C10 C9 131.4(4) . . ?
C8 N10 N9 103.6(3) . . ?
C10 C11 H11 126.4 . . ?
N12 C11 C10 107.2(4) . . ?
N12 C11 H11 126.4 . . ?
O2 N11 O3 124.1(4) . . ?
O2 N11 C8 118.1(4) . . ?
O3 N11 C8 117.7(3) . . ?
C10 C12 N14 127.4(4) . . ?
N13 C12 C10 114.2(4) . . ?
N13 C12 N14 118.4(4) . . ?
C11 N12 H12 123.5 . . ?
N13 N12 C11 112.9(3) . . ?
N13 N12 H12 123.5 . . ?
C12 N13 N12 103.0(3) . . ?
O4 N14 O5 124.1(4) . . ?
O4 N14 C12 118.9(4) . . ?
O5 N14 C12 117.0(4) . . ?
C13 O6 H6 109.5 . . ?
O6 C13 H13B 109.5 . . ?
O6 C13 H13A 109.5 . . ?
O6 C13 H13C 109.5 . . ?
H13B C13 H13A 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?

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
C1 N1 O1 N2 -0.1(4) . . . . ?
C1 C2 N2 O1 0.2(4) . . . . ?
C1 C2 N6 C3 2.3(5) . . . . ?
C1 C2 N6 C9 175.9(4) . . . . ?
C1 N3 C4 C3 -0.3(6) . . . . ?
C1 N3 C4 N5 -179.1(3) . . . . ?
C1 N3 C5 N4 179.4(4) . . . . ?
C1 N3 C5 C6 -2.2(7) . . . . ?
N1 C1 C2 N2 -0.3(5) . . . . ?
N1 C1 C2 N6 -179.9(3) . . . . ?
N1 C1 N3 C4 178.7(4) . . . . ?
N1 C1 N3 C5 -0.1(7) . . . . ?
N1 O1 N2 C2 -0.1(4) . . . . ?
C2 C1 N1 O1 0.2(4) . . . . ?
C2 C1 N3 C4 0.0(5) . . . . ?
C2 C1 N3 C5 -178.7(4) . . . . ?
C2 N6 C9 N7 -174.8(4) . . . . ?
C2 N6 C9 C10 1.7(7) . . . . ?
N2 C2 N6 C3 -177.2(4) . . . . ?
N2 C2 N6 C9 -3.6(7) . . . . ?
C3 C4 N5 N4 -179.1(4) . . . . ?
C3 N6 C9 N7 -0.5(5) . . . . ?
C3 N6 C9 C10 176.0(4) . . . . ?
N3 C1 N1 O1 -178.5(4) . . . . ?
N3 C1 C2 N2 178.6(3) . . . . ?
N3 C1 C2 N6 -1.0(5) . . . . ?
N3 C4 N5 N4 -0.4(5) . . . . ?
N3 C5 C6 C7 -64.3(6) . . . . ?
N3 C5 C6 C8 119.6(5) . . . . ?
C4 C3 N6 C2 -2.6(6) . . . . ?
C4 C3 N6 C9 -177.9(4) . . . . ?
C4 C3 N8 N7 177.6(4) . . . . ?
C4 N3 C5 N4 0.5(4) . . . . ?
C4 N3 C5 C6 178.9(4) . . . . ?
N4 C5 C6 C7 113.9(5) . . . . ?
N4 C5 C6 C8 -62.3(6) . . . . ?
C5 N3 C4 C3 178.8(4) . . . . ?
C5 N3 C4 N5 0.0(5) . . . . ?
C5 N4 N5 C4 0.7(5) . . . . ?
C5 C6 C7 N9 -176.1(3) . . . . ?
C5 C6 C8 N10 175.7(4) . . . . ?
C5 C6 C8 N11 -8.3(6) . . . . ?
N5 N4 C5 N3 -0.7(5) . . . . ?
N5 N4 C5 C6 -179.1(4) . . . . ?
C6 C7 N9 N10 -0.4(5) . . . . ?
C6 C8 N10 N9 0.9(4) . . . . ?
C6 C8 N11 O2 171.2(4) . . . . ?
C6 C8 N11 O3 -10.1(6) . . . . ?
N6 C2 N2 O1 179.8(4) . . . . ?
N6 C3 C4 N3 1.6(6) . . . . ?
N6 C3 C4 N5 -179.9(4) . . . . ?
N6 C3 N8 N7 -1.1(5) . . . . ?
N6 C9 C10 C11 -84.0(6) . . . . ?
N6 C9 C10 C12 94.9(5) . . . . ?
C7 C6 C8 N10 -1.2(4) . . . . ?
C7 C6 C8 N11 174.9(4) . . . . ?
C7 N9 N10 C8 -0.3(4) . . . . ?
N7 C9 C10 C11 91.8(6) . . . . ?
N7 C9 C10 C12 -89.3(6) . . . . ?
C8 C6 C7 N9 0.9(4) . . . . ?
N8 C3 C4 N3 -177.1(4) . . . . ?
N8 C3 C4 N5 1.4(8) . . . . ?
N8 C3 N6 C2 176.3(4) . . . . ?
N8 C3 N6 C9 1.0(5) . . . . ?
N8 N7 C9 N6 -0.2(5) . . . . ?
N8 N7 C9 C10 -176.5(4) . . . . ?
C9 N7 N8 C3 0.8(5) . . . . ?
C9 C10 C11 N12 179.3(4) . . . . ?
C9 C10 C12 N13 -179.3(4) . . . . ?
C9 C10 C12 N14 -0.1(7) . . . . ?
C10 C11 N12 N13 0.0(5) . . . . ?
C10 C12 N13 N12 0.2(5) . . . . ?
C10 C12 N14 O4 171.7(4) . . . . ?
C10 C12 N14 O5 -9.5(6) . . . . ?
N10 C8 N11 O2 -13.0(5) . . . . ?
N10 C8 N11 O3 165.8(3) . . . . ?
C11 C10 C12 N13 -0.2(5) . . . . ?
C11 C10 C12 N14 179.0(4) . . . . ?
C11 N12 N13 C12 -0.1(5) . . . . ?
N11 C8 N10 N9 -175.5(3) . . . . ?
C12 C10 C11 N12 0.1(5) . . . . ?
N13 C12 N14 O4 -9.1(6) . . . . ?
N13 C12 N14 O5 169.8(4) . . . . ?
N14 C12 N13 N12 -179.1(3) . . . . ?

_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_1
_database_code_depnum_ccdc_archive 'CCDC 2303259'
loop_
_audit_author_name
_audit_author_address
ZT
;Nanjing university of science and technology
China
;
_audit_update_record             
;
2023-10-24 deposited with the CCDC.	2024-01-15 downloaded from the CCDC.
;
_audit_creation_date             2023-04-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        123
_chemical_formula_moiety         'C8 H4 N8 O2, C H4 O'
_chemical_formula_sum            'C9 H8 N8 O3'
_chemical_formula_weight         276.23
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.7309(4)
_cell_length_b                   19.6818(10)
_cell_length_c                   6.9104(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.115(3)
_cell_angle_gamma                90
_cell_volume                     1146.40(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3608
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      67.843
_cell_measurement_theta_min      4.493
_shelx_estimated_absorpt_T_max   0.890
_shelx_estimated_absorpt_T_min   0.872
_exptl_absorpt_coefficient_mu    1.085
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0946 before and 0.0540 after correction.
The Ratio of minimum to maximum transmission is 0.8382.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            10625
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.920
_diffrn_reflns_theta_min         4.493
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1732
_reflns_number_total             2076
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2076
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.069
_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)+(0.0607P)²+0.3983P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1118
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), N8(H8), C8(H8a)
2.b Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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
N1 N 0.79139(18) 0.69908(8) 0.6028(2) 0.0296(4) Uani 1 1 d . . . . .
H1 H 0.848(3) 0.7399(13) 0.592(4) 0.056(7) Uiso 1 1 d . . . . .
O1 O 1.00837(15) 0.63137(7) 0.6489(2) 0.0376(4) Uani 1 1 d . . . . .
C1 C 0.8705(2) 0.63848(9) 0.6476(3) 0.0274(4) Uani 1 1 d . . . . .
N2 N 0.54963(19) 0.75911(8) 0.5777(3) 0.0378(4) Uani 1 1 d . . . . .
O2 O 0.40146(16) 0.73727(7) 0.5973(3) 0.0430(4) Uani 1 1 d . . . . .
C2 C 0.6366(2) 0.70446(9) 0.6086(3) 0.0276(4) Uani 1 1 d . . . . .
C3 C 0.77526(19) 0.58094(8) 0.6924(3) 0.0237(4) Uani 1 1 d . . . . .
N3 N 0.40218(18) 0.66860(8) 0.6410(3) 0.0348(4) Uani 1 1 d . . . . .
N4 N 0.61628(15) 0.58596(7) 0.6901(2) 0.0219(3) Uani 1 1 d . . . . .
C4 C 0.54511(19) 0.64938(9) 0.6482(3) 0.0240(4) Uani 1 1 d . . . . .
C5 C 0.57374(19) 0.52138(8) 0.7354(2) 0.0216(4) Uani 1 1 d . . . . .
N5 N 0.82516(16) 0.51874(7) 0.7359(2) 0.0256(3) Uani 1 1 d . . . . .
N6 N 0.69832(16) 0.48122(7) 0.7628(2) 0.0256(3) Uani 1 1 d . . . . .
C6 C 0.41915(19) 0.49867(9) 0.7506(2) 0.0225(4) Uani 1 1 d . . . . .
N7 N 0.23484(17) 0.42563(7) 0.8033(2) 0.0285(4) Uani 1 1 d . . . . .
C7 C 0.2773(2) 0.53292(9) 0.7246(3) 0.0263(4) Uani 1 1 d . . . . .
H7 H 0.258435 0.579470 0.690293 0.032 Uiso 1 1 calc R U . . .
N8 N 0.17205(17) 0.48842(7) 0.7568(2) 0.0274(4) Uani 1 1 d . . . . .
H8 H 0.072447 0.498603 0.748757 0.033 Uiso 1 1 calc R U . . .
C8 C 0.3861(2) 0.43170(9) 0.7994(3) 0.0263(4) Uani 1 1 d . . . . .
H8A H 0.461280 0.395759 0.825842 0.032 Uiso 1 1 calc R U . . .
O3 O 0.92292(14) 0.81954(6) 0.5717(2) 0.0338(3) Uani 1 1 d . . . . .
H3 H 0.876536 0.851774 0.612489 0.051 Uiso 1 1 calc R U . . .
C9 C 1.0896(3) 0.82534(14) 0.6558(5) 0.0586(7) Uani 1 1 d . . . . .
H9A H 1.142937 0.785591 0.617981 0.088 Uiso 1 1 calc R U . . .
H9B H 1.112060 0.827791 0.802146 0.088 Uiso 1 1 calc R U . . .
H9C H 1.128533 0.866617 0.605092 0.088 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
N1 H1 0.96(3) . ?
N1 C1 1.372(2) . ?
N1 C2 1.367(2) . ?
O1 C1 1.210(2) . ?
C1 C3 1.484(2) . ?
N2 O2 1.403(2) . ?
N2 C2 1.302(2) . ?
O2 N3 1.385(2) . ?
C2 C4 1.415(2) . ?
C3 N4 1.387(2) . ?
C3 N5 1.308(2) . ?
N3 C4 1.292(2) . ?
N4 C4 1.391(2) . ?
N4 C5 1.383(2) . ?
C5 N6 1.318(2) . ?
C5 C6 1.452(2) . ?
N5 N6 1.383(2) . ?
C6 C7 1.380(2) . ?
C6 C8 1.409(2) . ?
N7 N8 1.356(2) . ?
N7 C8 1.333(2) . ?
C7 H7 0.9500 . ?
C7 N8 1.329(2) . ?
N8 H8 0.8800 . ?
C8 H8A 0.9500 . ?
O3 H3 0.8400 . ?
O3 C9 1.424(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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
C1 N1 H1 120.4(16) . . ?
C2 N1 H1 118.4(16) . . ?
C2 N1 C1 120.26(16) . . ?
N1 C1 C3 115.72(15) . . ?
O1 C1 N1 122.90(17) . . ?
O1 C1 C3 121.37(16) . . ?
C2 N2 O2 104.11(14) . . ?
N3 O2 N2 111.61(13) . . ?
N1 C2 C4 123.96(16) . . ?
N2 C2 N1 126.73(17) . . ?
N2 C2 C4 109.30(16) . . ?
N4 C3 C1 123.79(15) . . ?
N5 C3 C1 126.23(15) . . ?
N5 C3 N4 109.98(14) . . ?
C4 N3 O2 104.08(14) . . ?
C3 N4 C4 117.23(14) . . ?
C5 N4 C3 105.00(13) . . ?
C5 N4 C4 137.77(14) . . ?
N3 C4 C2 110.88(15) . . ?
N3 C4 N4 130.16(16) . . ?
N4 C4 C2 118.95(15) . . ?
N4 C5 C6 127.53(15) . . ?
N6 C5 N4 108.88(14) . . ?
N6 C5 C6 123.58(15) . . ?
C3 N5 N6 107.47(13) . . ?
C5 N6 N5 108.67(14) . . ?
C7 C6 C5 131.30(16) . . ?
C7 C6 C8 104.78(15) . . ?
C8 C6 C5 123.92(15) . . ?
C8 N7 N8 104.76(14) . . ?
C6 C7 H7 126.5 . . ?
N8 C7 C6 107.00(15) . . ?
N8 C7 H7 126.5 . . ?
N7 N8 H8 123.7 . . ?
C7 N8 N7 112.68(14) . . ?
C7 N8 H8 123.7 . . ?
C6 C8 H8A 124.6 . . ?
N7 C8 C6 110.77(15) . . ?
N7 C8 H8A 124.6 . . ?
C9 O3 H3 109.5 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
N1 C1 C3 N4 0.2(3) . . . . ?
N1 C1 C3 N5 178.99(17) . . . . ?
N1 C2 C4 N3 -178.89(17) . . . . ?
N1 C2 C4 N4 2.1(3) . . . . ?
O1 C1 C3 N4 -179.00(17) . . . . ?
O1 C1 C3 N5 -0.2(3) . . . . ?
C1 N1 C2 N2 177.05(19) . . . . ?
C1 N1 C2 C4 -3.7(3) . . . . ?
C1 C3 N4 C4 -1.7(2) . . . . ?
C1 C3 N4 C5 178.77(16) . . . . ?
C1 C3 N5 N6 -178.75(16) . . . . ?
N2 O2 N3 C4 0.1(2) . . . . ?
N2 C2 C4 N3 0.5(2) . . . . ?
N2 C2 C4 N4 -178.57(16) . . . . ?
O2 N2 C2 N1 178.98(18) . . . . ?
O2 N2 C2 C4 -0.4(2) . . . . ?
O2 N3 C4 C2 -0.4(2) . . . . ?
O2 N3 C4 N4 178.56(18) . . . . ?
C2 N1 C1 O1 -178.37(17) . . . . ?
C2 N1 C1 C3 2.4(2) . . . . ?
C2 N2 O2 N3 0.2(2) . . . . ?
C3 N4 C4 C2 0.6(2) . . . . ?
C3 N4 C4 N3 -178.20(18) . . . . ?
C3 N4 C5 N6 0.13(18) . . . . ?
C3 N4 C5 C6 -179.46(16) . . . . ?
C3 N5 N6 C5 -0.08(19) . . . . ?
N4 C3 N5 N6 0.17(19) . . . . ?
N4 C5 N6 N5 -0.03(19) . . . . ?
N4 C5 C6 C7 0.5(3) . . . . ?
N4 C5 C6 C8 -179.44(16) . . . . ?
C4 N4 C5 N6 -179.23(19) . . . . ?
C4 N4 C5 C6 1.2(3) . . . . ?
C5 N4 C4 C2 179.93(18) . . . . ?
C5 N4 C4 N3 1.1(3) . . . . ?
C5 C6 C7 N8 -179.81(17) . . . . ?
C5 C6 C8 N7 179.78(15) . . . . ?
N5 C3 N4 C4 179.33(15) . . . . ?
N5 C3 N4 C5 -0.18(19) . . . . ?
N6 C5 C6 C7 -179.08(18) . . . . ?
N6 C5 C6 C8 1.0(3) . . . . ?
C6 C5 N6 N5 179.58(15) . . . . ?
C6 C7 N8 N7 0.0(2) . . . . ?
C7 C6 C8 N7 -0.1(2) . . . . ?
N8 N7 C8 C6 0.13(19) . . . . ?
C8 C6 C7 N8 0.10(19) . . . . ?
C8 N7 N8 C7 -0.07(19) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
