# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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 1900161'
loop_
_audit_author_name
_audit_author_address
'jie Tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-08-14 deposited with the CCDC.	2020-08-25 downloaded from the CCDC.
;
_audit_creation_date             2020-08-09
_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         'C13 H6 N8 O12'
_chemical_formula_sum            'C13 H6 N8 O12'
_chemical_formula_weight         466.26
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.4477(6)
_cell_length_b                   9.0068(5)
_cell_length_c                   23.0450(17)
_cell_angle_alpha                90
_cell_angle_beta                 93.494(3)
_cell_angle_gamma                90
_cell_volume                     1750.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2701
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.23
_cell_measurement_theta_min      3.31
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.951
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker;SADABS;2018
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12208
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.376
_diffrn_reflns_theta_min         3.310
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CMOS area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2163
_reflns_number_total             3185
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_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         0.294
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.0033(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         3185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0599
_refine_ls_restrained_S_all      1.097
_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)+(0.0274P)²+1.4196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1060
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C7(H7), C11(H11), C13(H13)
;
_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 0.7496(4) 0.9192(3) 0.13000(12) 0.0164(7) Uani 1 1 d . . . . .
H1 H 0.842089 0.979273 0.130674 0.020 Uiso 1 1 calc R . . . .
C2 C 0.8908(3) 0.6553(3) -0.03429(13) 0.0148(7) Uani 1 1 d . . . . .
C3 C 0.8281(3) 0.6672(3) 0.02166(13) 0.0138(6) Uani 1 1 d . . . . .
C4 C 0.7413(3) 0.5399(3) 0.03797(13) 0.0168(7) Uani 1 1 d . . . . .
C5 C 0.7084(4) 0.4217(3) 0.00224(13) 0.0197(7) Uani 1 1 d . . . . .
H5 H 0.643989 0.342227 0.014183 0.024 Uiso 1 1 calc R . . . .
C6 C 0.7714(4) 0.4203(3) -0.05194(14) 0.0191(7) Uani 1 1 d . . . . .
C7 C 0.8634(3) 0.5344(3) -0.07044(13) 0.0163(7) Uani 1 1 d . . . . .
H7 H 0.907507 0.530368 -0.107366 0.020 Uiso 1 1 calc R . . . .
C8 C 0.6107(3) 0.8788(3) 0.22345(12) 0.0152(7) Uani 1 1 d . . . . .
C9 C 0.6188(3) 0.9461(3) 0.16914(12) 0.0147(6) Uani 1 1 d . . . . .
C10 C 0.4866(4) 1.0325(3) 0.15126(12) 0.0159(7) Uani 1 1 d . . . . .
C11 C 0.3533(4) 1.0464(3) 0.18264(13) 0.0170(7) Uani 1 1 d . . . . .
H11 H 0.265466 1.105181 0.168872 0.020 Uiso 1 1 calc R . . . .
C12 C 0.3530(4) 0.9714(3) 0.23486(13) 0.0172(7) Uani 1 1 d . . . . .
C13 C 0.4797(4) 0.8886(3) 0.25657(13) 0.0173(7) Uani 1 1 d . . . . .
H13 H 0.477616 0.839838 0.293058 0.021 Uiso 1 1 calc R . . . .
N1 N 0.8431(3) 0.7877(3) 0.05605(11) 0.0173(6) Uani 1 1 d . . . . .
H1A H 0.903(4) 0.856(3) 0.0459(14) 0.021 Uiso 1 1 d R . . . .
N2 N 0.7283(3) 0.8103(3) 0.09579(10) 0.0154(6) Uani 1 1 d . . . . .
N3 N 0.9809(3) 0.7762(3) -0.05794(11) 0.0186(6) Uani 1 1 d . . . . .
N4 N 0.6958(3) 0.5196(3) 0.09877(12) 0.0217(6) Uani 1 1 d . . . . .
N5 N 0.7420(3) 0.2916(3) -0.08978(13) 0.0308(7) Uani 1 1 d . . . . .
N6 N 0.7464(3) 0.7922(3) 0.24821(12) 0.0230(6) Uani 1 1 d . . . . .
N7 N 0.4868(3) 1.1123(3) 0.09553(11) 0.0241(7) Uani 1 1 d . . . . .
N8 N 0.2083(3) 0.9774(3) 0.26748(12) 0.0246(6) Uani 1 1 d . . . . .
O1 O 0.8026(3) 0.5310(2) 0.13724(10) 0.0283(6) Uani 1 1 d . . . . .
O2 O 0.5595(3) 0.4847(3) 0.10600(11) 0.0395(7) Uani 1 1 d . . . . .
O3 O 0.8019(3) 0.2894(3) -0.13690(11) 0.0457(7) Uani 1 1 d . . . . .
O4 O 0.6609(4) 0.1917(3) -0.07136(11) 0.0524(8) Uani 1 1 d . . . . .
O5 O 0.9972(3) 0.7798(3) -0.11016(9) 0.0336(6) Uani 1 1 d . . . . .
O6 O 1.0370(3) 0.8713(2) -0.02379(10) 0.0274(6) Uani 1 1 d . . . . .
O7 O 0.8728(3) 0.8008(3) 0.22539(10) 0.0375(7) Uani 1 1 d . . . . .
O8 O 0.7250(3) 0.7173(3) 0.29110(11) 0.0412(7) Uani 1 1 d . . . . .
O9 O 0.6152(3) 1.1375(3) 0.07555(11) 0.0377(7) Uani 1 1 d . . . . .
O10 O 0.3593(3) 1.1506(3) 0.07270(11) 0.0427(7) Uani 1 1 d . . . . .
O11 O 0.2018(3) 0.8939(3) 0.30929(10) 0.0324(6) Uani 1 1 d . . . . .
O12 O 0.1035(3) 1.0629(3) 0.25068(11) 0.0404(7) 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
C1 H1 0.9500 . ?
C1 C9 1.488(4) . ?
C1 N2 1.264(4) . ?
C2 C3 1.427(4) . ?
C2 C7 1.382(4) . ?
C2 N3 1.454(4) . ?
C3 C4 1.424(4) . ?
C3 N1 1.345(4) . ?
C4 C5 1.364(4) . ?
C4 N4 1.487(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(4) . ?
C6 C7 1.372(4) . ?
C6 N5 1.463(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.396(4) . ?
C8 C13 1.385(4) . ?
C8 N6 1.473(4) . ?
C9 C10 1.402(4) . ?
C10 C11 1.381(4) . ?
C10 N7 1.472(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.380(4) . ?
C12 C13 1.374(4) . ?
C12 N8 1.474(4) . ?
C13 H13 0.9500 . ?
N1 H1A 0.84(3) . ?
N1 N2 1.389(3) . ?
N3 O5 1.220(3) . ?
N3 O6 1.238(3) . ?
N4 O1 1.230(3) . ?
N4 O2 1.215(3) . ?
N5 O3 1.226(3) . ?
N5 O4 1.223(3) . ?
N6 O7 1.221(3) . ?
N6 O8 1.219(3) . ?
N7 O9 1.226(3) . ?
N7 O10 1.219(3) . ?
N8 O11 1.226(3) . ?
N8 O12 1.219(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
C9 C1 H1 122.5 . . ?
N2 C1 H1 122.5 . . ?
N2 C1 C9 115.0(3) . . ?
C3 C2 N3 120.9(2) . . ?
C7 C2 C3 123.1(3) . . ?
C7 C2 N3 115.9(3) . . ?
C4 C3 C2 113.8(3) . . ?
N1 C3 C2 124.5(2) . . ?
N1 C3 C4 121.7(3) . . ?
C3 C4 N4 121.0(3) . . ?
C5 C4 C3 123.9(3) . . ?
C5 C4 N4 114.7(2) . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.4(3) . . ?
C6 C5 H5 120.8 . . ?
C5 C6 N5 118.9(3) . . ?
C7 C6 C5 121.9(3) . . ?
C7 C6 N5 119.1(3) . . ?
C2 C7 H7 120.7 . . ?
C6 C7 C2 118.7(3) . . ?
C6 C7 H7 120.7 . . ?
C9 C8 N6 119.9(3) . . ?
C13 C8 C9 123.4(3) . . ?
C13 C8 N6 116.7(3) . . ?
C8 C9 C1 123.5(3) . . ?
C8 C9 C10 115.0(3) . . ?
C10 C9 C1 121.3(3) . . ?
C9 C10 N7 119.0(3) . . ?
C11 C10 C9 123.8(3) . . ?
C11 C10 N7 117.2(3) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 C10 117.2(3) . . ?
C12 C11 H11 121.4 . . ?
C11 C12 N8 118.2(3) . . ?
C13 C12 C11 122.7(3) . . ?
C13 C12 N8 119.1(3) . . ?
C8 C13 H13 121.1 . . ?
C12 C13 C8 117.7(3) . . ?
C12 C13 H13 121.1 . . ?
C3 N1 H1A 118(2) . . ?
C3 N1 N2 117.5(2) . . ?
N2 N1 H1A 122(2) . . ?
C1 N2 N1 116.5(2) . . ?
O5 N3 C2 118.9(2) . . ?
O5 N3 O6 123.2(2) . . ?
O6 N3 C2 118.0(2) . . ?
O1 N4 C4 116.7(2) . . ?
O2 N4 C4 117.6(3) . . ?
O2 N4 O1 125.6(3) . . ?
O3 N5 C6 118.5(3) . . ?
O4 N5 C6 117.0(3) . . ?
O4 N5 O3 124.5(3) . . ?
O7 N6 C8 118.7(3) . . ?
O8 N6 C8 117.2(3) . . ?
O8 N6 O7 124.1(3) . . ?
O9 N7 C10 117.8(3) . . ?
O10 N7 C10 117.8(3) . . ?
O10 N7 O9 124.4(3) . . ?
O11 N8 C12 117.2(3) . . ?
O12 N8 C12 118.0(3) . . ?
O12 N8 O11 124.8(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_mo_22020288_0m
_database_code_depnum_ccdc_archive 'CCDC 2011493'
loop_
_audit_author_name
_audit_author_address
'jie Tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-08-14 deposited with the CCDC.	2020-08-25 downloaded from the CCDC.
;
_audit_creation_date             2020-08-09
_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         '2(C3 H7 N O), C16 H8 N14 O12'
_chemical_formula_sum            'C22 H22 N16 O14'
_chemical_formula_weight         734.55
_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      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                   7.8751(4)
_cell_length_b                   8.0958(3)
_cell_length_c                   12.3520(5)
_cell_angle_alpha                81.816(2)
_cell_angle_beta                 80.771(2)
_cell_angle_gamma                80.036(2)
_cell_volume                     760.25(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3258
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.322
_cell_measurement_theta_min      2.572
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0661 before and 0.0424 after correction. The Ratio of minimum to maximum transmission is 0.9163. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             378
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8624
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.469
_diffrn_reflns_theta_min         2.572
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_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                2335
_reflns_number_total             3092
_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         0.242
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3092
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.057
_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)+(0.0337P)²+0.3059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0983
_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
2. Restrained distances
 O6-N3 \\sim O8-N3
 with sigma of 0.02
3. Others
 Fixed Sof: O8(0.75) O6(0.25)
4.a Aromatic/amide H refined with riding coordinates:
 N5(H5), C1(H1), C10(H10), C7(H7), C5(H5A)
4.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_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
O7 O 0.49748(16) 0.14734(15) 0.82901(12) 0.0388(3) Uani 1 1 d . . . . .
O4 O 0.10479(17) 0.88495(18) 0.20758(12) 0.0436(4) Uani 1 1 d . . . . .
O1 O 0.34779(18) 0.75608(16) 0.63570(12) 0.0420(4) Uani 1 1 d . . . . .
O2 O 0.07412(19) 0.84929(18) 0.62526(12) 0.0508(4) Uani 1 1 d . . . . .
O3 O 0.20425(19) 0.65231(18) 0.13496(11) 0.0452(4) Uani 1 1 d . . . . .
N6 N 0.11546(19) 0.35511(18) 1.01139(12) 0.0299(3) Uani 1 1 d . . . . .
O5 O 0.3115(2) 0.13812(17) 0.36674(13) 0.0496(4) Uani 1 1 d . . . . .
N4 N 0.18264(19) 0.46235(17) 0.72317(12) 0.0284(3) Uani 1 1 d . . . . .
N7 N 0.01148(19) 0.40333(18) 1.10024(12) 0.0307(4) Uani 1 1 d . . . . .
N5 N 0.21044(19) 0.39393(18) 0.82653(12) 0.0309(4) Uani 1 1 d . . . . .
H5 H 0.298497 0.312849 0.836673 0.037 Uiso 1 1 calc R . . . .
N8 N 0.42013(18) -0.11346(17) 0.87946(12) 0.0296(3) Uani 1 1 d . . . . .
N2 N 0.2121(2) 0.76105(18) 0.59840(13) 0.0339(4) Uani 1 1 d . . . . .
N1 N 0.16636(19) 0.7353(2) 0.21365(13) 0.0348(4) Uani 1 1 d . . . . .
N3 N 0.2836(2) 0.2068(2) 0.44955(15) 0.0442(4) Uani 1 1 d D . . . .
C8 C 0.1000(2) 0.4522(2) 0.91535(14) 0.0261(4) Uani 1 1 d . . . . .
C2 C 0.2156(2) 0.6555(2) 0.50975(15) 0.0277(4) Uani 1 1 d . . . . .
O8 O 0.2494(4) 0.1323(4) 0.5418(3) 0.0580(8) Uani 0.75 1 d D . P A 1
C1 C 0.1847(2) 0.7413(2) 0.40926(15) 0.0292(4) Uani 1 1 d . . . . .
H1 H 0.156502 0.860957 0.399540 0.035 Uiso 1 1 calc R . . . .
C4 C 0.2578(2) 0.3931(2) 0.43898(16) 0.0316(4) Uani 1 1 d . . . . .
C10 C 0.5334(2) -0.0074(2) 0.85375(16) 0.0324(4) Uani 1 1 d . . . . .
H10 H 0.652872 -0.053125 0.854187 0.039 Uiso 1 1 calc R . . . .
C3 C 0.2535(2) 0.4783(2) 0.53116(15) 0.0290(4) Uani 1 1 d . . . . .
C6 C 0.1962(2) 0.6475(2) 0.32251(15) 0.0294(4) Uani 1 1 d . . . . .
C7 C 0.2823(2) 0.3976(2) 0.64236(15) 0.0311(4) Uani 1 1 d . . . . .
H7 H 0.369949 0.302780 0.653734 0.037 Uiso 1 1 calc R . . . .
C5 C 0.2307(2) 0.4740(2) 0.33592(15) 0.0328(4) Uani 1 1 d . . . . .
H5A H 0.235812 0.411558 0.275642 0.039 Uiso 1 1 calc R . . . .
C11 C 0.4762(3) -0.2937(2) 0.90266(17) 0.0394(5) Uani 1 1 d . . . . .
H11A H 0.442005 -0.352543 0.847436 0.059 Uiso 1 1 calc GR . . . .
H11B H 0.421368 -0.334122 0.976366 0.059 Uiso 1 1 calc GR . . . .
H11C H 0.603068 -0.316194 0.899837 0.059 Uiso 1 1 calc GR . . . .
C9 C 0.2351(2) -0.0538(2) 0.8789(2) 0.0442(5) Uani 1 1 d . . . . .
H9A H 0.191182 0.014877 0.939689 0.066 Uiso 1 1 calc GR . . . .
H9B H 0.172703 -0.150719 0.888287 0.066 Uiso 1 1 calc GR . . . .
H9C H 0.216780 0.014748 0.808527 0.066 Uiso 1 1 calc GR . . . .
O6 O 0.3556(13) 0.1291(11) 0.5377(8) 0.067(3) Uani 0.25 1 d D . P A 2


_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
O7 C10 1.240(2) . ?
O4 N1 1.221(2) . ?
O1 N2 1.2220(19) . ?
O2 N2 1.2184(19) . ?
O3 N1 1.2285(19) . ?
N6 N7 1.323(2) . ?
N6 C8 1.337(2) . ?
O5 N3 1.204(2) . ?
N4 N5 1.353(2) . ?
N4 C7 1.282(2) . ?
N7 C8 1.345(2) 2_567 ?
N5 H5 0.8800 . ?
N5 C8 1.372(2) . ?
N8 C10 1.316(2) . ?
N8 C11 1.451(2) . ?
N8 C9 1.454(2) . ?
N2 C2 1.476(2) . ?
N1 C6 1.463(2) . ?
N3 O8 1.223(3) . ?
N3 C4 1.477(2) . ?
N3 O6 1.335(9) . ?
C2 C1 1.370(2) . ?
C2 C3 1.409(2) . ?
C1 H1 0.9500 . ?
C1 C6 1.382(2) . ?
C4 C3 1.405(2) . ?
C4 C5 1.377(3) . ?
C10 H10 0.9500 . ?
C3 C7 1.469(3) . ?
C6 C5 1.375(3) . ?
C7 H7 0.9500 . ?
C5 H5A 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
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
N7 N6 C8 117.74(14) . . ?
C7 N4 N5 117.40(15) . . ?
N6 N7 C8 116.05(15) . 2_567 ?
N4 N5 H5 120.3 . . ?
N4 N5 C8 119.34(14) . . ?
C8 N5 H5 120.3 . . ?
C10 N8 C11 121.26(15) . . ?
C10 N8 C9 120.60(15) . . ?
C11 N8 C9 118.04(15) . . ?
O1 N2 C2 117.55(14) . . ?
O2 N2 O1 126.03(15) . . ?
O2 N2 C2 116.38(15) . . ?
O4 N1 O3 124.79(17) . . ?
O4 N1 C6 117.88(15) . . ?
O3 N1 C6 117.33(16) . . ?
O5 N3 O8 123.1(2) . . ?
O5 N3 C4 118.67(18) . . ?
O5 N3 O6 118.5(4) . . ?
O8 N3 C4 117.3(2) . . ?
O6 N3 C4 115.1(4) . . ?
N6 C8 N7 126.21(16) . 2_567 ?
N6 C8 N5 114.66(15) . . ?
N7 C8 N5 119.13(16) 2_567 . ?
C1 C2 N2 115.71(15) . . ?
C1 C2 C3 124.46(16) . . ?
C3 C2 N2 119.81(16) . . ?
C2 C1 H1 121.2 . . ?
C2 C1 C6 117.51(16) . . ?
C6 C1 H1 121.2 . . ?
C3 C4 N3 120.74(17) . . ?
C5 C4 N3 115.61(16) . . ?
C5 C4 C3 123.58(16) . . ?
O7 C10 N8 125.52(17) . . ?
O7 C10 H10 117.2 . . ?
N8 C10 H10 117.2 . . ?
C2 C3 C7 120.42(16) . . ?
C4 C3 C2 114.06(17) . . ?
C4 C3 C7 125.52(16) . . ?
C1 C6 N1 118.95(16) . . ?
C5 C6 N1 118.98(16) . . ?
C5 C6 C1 122.05(18) . . ?
N4 C7 C3 116.25(16) . . ?
N4 C7 H7 121.9 . . ?
C3 C7 H7 121.9 . . ?
C4 C5 H5A 120.9 . . ?
C6 C5 C4 118.30(17) . . ?
C6 C5 H5A 120.9 . . ?
N8 C11 H11A 109.5 . . ?
N8 C11 H11B 109.5 . . ?
N8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N8 C9 H9A 109.5 . . ?
N8 C9 H9B 109.5 . . ?
N8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_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_22019555_0m
_database_code_depnum_ccdc_archive 'CCDC 2005063'
loop_
_audit_author_name
_audit_author_address
'jie Tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-08-14 deposited with the CCDC.	2020-08-25 downloaded from the CCDC.
;
_audit_creation_date             2020-08-09
_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         'C15 H8 N10 O10'
_chemical_formula_sum            'C15 H8 N10 O10'
_chemical_formula_weight         488.31
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.618(10)
_cell_length_b                   15.497(6)
_cell_length_c                   9.320(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.757(10)
_cell_angle_gamma                90
_cell_volume                     3809(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2291
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.091
_cell_measurement_theta_min      2.594
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.994
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0986 before and 0.0758 after correction. The Ratio of minimum to maximum transmission is 0.8231. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   
'Because the crystal size is small and the high Angle has no diffraction point, the Rint and R values are high. After many tests, this data is the best.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1106
_diffrn_reflns_av_unetI/netI     0.1223
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11573
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.516
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_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                1795
_reflns_number_total             3250
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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         0.616
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         3250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1762
_refine_ls_R_factor_gt           0.1084
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1029P)²+46.9454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2653
_refine_ls_wR_factor_ref         0.3001
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.762(4)
 0.238(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C12(H12), C1(H1), C9(H9), C14(H14)
3.b X=CH2 refined with riding coordinates:
 N5(H5A,H5B)
;
_atom_sites_solution_hydrogens   geom
_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 0.65932(18) 0.5535(3) 0.5980(4) 0.0320(11) Uani 1 1 d . . . . .
O1 O 0.79546(18) 0.7609(3) 0.1133(5) 0.0346(12) Uani 1 1 d . . . . .
O2 O 0.78578(18) 0.6212(3) 0.1019(5) 0.0338(12) Uani 1 1 d . . . . .
O3 O 0.69539(19) 0.4798(3) 0.4436(5) 0.0354(12) Uani 1 1 d . . . . .
O9 O 0.58441(19) 0.4462(3) 0.8329(5) 0.0387(13) Uani 1 1 d . . . . .
O10 O 0.5361(2) 0.4603(3) 0.6264(5) 0.0419(14) Uani 1 1 d . . . . .
O7 O 0.6157(2) 0.8212(3) 1.0449(5) 0.0446(14) Uani 1 1 d . . . . .
N6 N 0.6330(2) 0.8525(3) 0.6080(5) 0.0310(14) Uani 1 1 d . . . . .
N3 N 0.6781(2) 0.8634(3) 0.4155(5) 0.0254(13) Uani 1 1 d . . . . .
O8 O 0.6244(2) 0.6916(3) 1.1235(5) 0.0502(15) Uani 1 1 d . . . . .
N1 N 0.7768(2) 0.6927(4) 0.1492(5) 0.0296(14) Uani 1 1 d . . . . .
O6 O 0.5088(2) 0.8344(4) 0.5279(6) 0.0564(16) Uani 1 1 d . . . . .
N10 N 0.5622(2) 0.4914(4) 0.7341(6) 0.0354(15) Uani 1 1 d . . . . .
O5 O 0.5487(2) 0.7481(4) 0.3976(5) 0.0537(16) Uani 1 1 d . . . . .
N4 N 0.7009(2) 0.9159(3) 0.3226(5) 0.0278(14) Uani 1 1 d . . . . .
N2 N 0.6823(2) 0.5469(3) 0.4939(6) 0.0292(14) Uani 1 1 d . . . . .
N5 N 0.6464(2) 0.9882(3) 0.5055(6) 0.0389(15) Uani 1 1 d . . . . .
H5A H 0.629825 1.016631 0.566125 0.047 Uiso 1 1 calc R . . . .
H5B H 0.659985 1.016143 0.438249 0.047 Uiso 1 1 calc R . . . .
N7 N 0.6070(2) 0.9029(4) 0.7006(6) 0.0377(15) Uani 1 1 d . . . . .
N9 N 0.6112(2) 0.7426(4) 1.0294(5) 0.0332(15) Uani 1 1 d . . . . .
C4 C 0.6898(2) 0.7791(4) 0.3989(6) 0.0240(15) Uani 1 1 d . . . . .
C7 C 0.7275(3) 0.8651(4) 0.2516(7) 0.0281(16) Uani 1 1 d . . . . .
H7 H 0.747747 0.884122 0.181177 0.034 Uiso 1 1 calc R . . . .
C6 C 0.6959(2) 0.6289(4) 0.4224(7) 0.0253(15) Uani 1 1 d . . . . .
N8 N 0.5359(2) 0.7721(4) 0.5114(7) 0.0425(17) Uani 1 1 d . . . . .
C5 C 0.6763(2) 0.7042(4) 0.4659(7) 0.0263(16) Uani 1 1 d . . . . .
H5 H 0.654504 0.705458 0.538619 0.032 Uiso 1 1 calc R . . . .
C15 C 0.5544(3) 0.7207(5) 0.6423(7) 0.0336(17) Uani 1 1 d . . . . .
C3 C 0.7227(3) 0.7770(4) 0.2928(6) 0.0287(16) Uani 1 1 d . . . . .
C13 C 0.5673(3) 0.5840(4) 0.7466(7) 0.0297(16) Uani 1 1 d . . . . .
C11 C 0.5898(3) 0.7076(5) 0.8862(7) 0.0325(17) Uani 1 1 d . . . . .
C8 C 0.6507(3) 0.9033(4) 0.5156(7) 0.0291(16) Uani 1 1 d . . . . .
C10 C 0.5743(3) 0.7641(5) 0.7700(7) 0.0345(17) Uani 1 1 d . . . . .
C12 C 0.5867(3) 0.6201(5) 0.8756(7) 0.0318(17) Uani 1 1 d . . . . .
H12 H 0.597843 0.584755 0.956955 0.038 Uiso 1 1 calc R . . . .
C1 C 0.7276(3) 0.6213(4) 0.3174(7) 0.0287(16) Uani 1 1 d . . . . .
H1 H 0.739301 0.566714 0.289641 0.034 Uiso 1 1 calc R . . . .
C2 C 0.7414(3) 0.6968(4) 0.2548(7) 0.0298(17) Uani 1 1 d . . . . .
C9 C 0.5803(3) 0.8586(5) 0.7767(8) 0.0382(19) Uani 1 1 d . . . . .
H9 H 0.562677 0.888922 0.843209 0.046 Uiso 1 1 calc R . . . .
C14 C 0.5508(3) 0.6341(5) 0.6256(7) 0.0358(18) Uani 1 1 d . . . . .
H14 H 0.537608 0.608751 0.535569 0.043 Uiso 1 1 calc R . . . .


_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 N2 1.219(7) . ?
O1 N1 1.233(7) . ?
O2 N1 1.228(7) . ?
O3 N2 1.212(7) . ?
O9 N10 1.242(7) . ?
O10 N10 1.240(7) . ?
O7 N9 1.230(7) . ?
N6 N7 1.412(8) . ?
N6 C8 1.302(8) . ?
N3 N4 1.387(7) . ?
N3 C4 1.358(8) . ?
N3 C8 1.402(8) . ?
O8 N9 1.199(7) . ?
N1 C2 1.453(8) . ?
O6 N8 1.228(8) . ?
N10 C13 1.444(9) . ?
O5 N8 1.215(8) . ?
N4 C7 1.299(8) . ?
N2 C6 1.501(8) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C8 1.322(8) . ?
N7 C9 1.272(9) . ?
N9 C11 1.481(8) . ?
C4 C5 1.388(9) . ?
C4 C3 1.406(9) . ?
C7 H7 0.9500 . ?
C7 C3 1.428(9) . ?
C6 C5 1.363(9) . ?
C6 C1 1.380(9) . ?
N8 C15 1.484(9) . ?
C5 H5 0.9500 . ?
C15 C10 1.407(9) . ?
C15 C14 1.353(10) . ?
C3 C2 1.403(9) . ?
C13 C12 1.363(9) . ?
C13 C14 1.391(9) . ?
C11 C10 1.411(9) . ?
C11 C12 1.361(10) . ?
C10 C9 1.473(10) . ?
C12 H12 0.9500 . ?
C1 H1 0.9500 . ?
C1 C2 1.379(9) . ?
C9 H9 0.9500 . ?
C14 H14 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
C8 N6 N7 108.7(5) . . ?
N4 N3 C8 117.9(5) . . ?
C4 N3 N4 111.4(5) . . ?
C4 N3 C8 130.5(5) . . ?
O1 N1 C2 117.9(5) . . ?
O2 N1 O1 124.8(5) . . ?
O2 N1 C2 117.2(5) . . ?
O9 N10 C13 118.1(5) . . ?
O10 N10 O9 122.7(6) . . ?
O10 N10 C13 119.2(6) . . ?
C7 N4 N3 106.2(5) . . ?
O4 N2 C6 117.3(5) . . ?
O3 N2 O4 125.6(5) . . ?
O3 N2 C6 117.1(5) . . ?
H5A N5 H5B 120.0 . . ?
C8 N5 H5A 120.0 . . ?
C8 N5 H5B 120.0 . . ?
C9 N7 N6 113.6(6) . . ?
O7 N9 C11 119.2(5) . . ?
O8 N9 O7 123.5(6) . . ?
O8 N9 C11 117.2(6) . . ?
N3 C4 C5 132.5(6) . . ?
N3 C4 C3 106.1(5) . . ?
C5 C4 C3 121.4(6) . . ?
N4 C7 H7 124.2 . . ?
N4 C7 C3 111.5(6) . . ?
C3 C7 H7 124.2 . . ?
C5 C6 N2 117.9(6) . . ?
C5 C6 C1 125.3(6) . . ?
C1 C6 N2 116.8(5) . . ?
O6 N8 C15 117.0(6) . . ?
O5 N8 O6 126.1(6) . . ?
O5 N8 C15 116.9(6) . . ?
C4 C5 H5 121.6 . . ?
C6 C5 C4 116.7(6) . . ?
C6 C5 H5 121.6 . . ?
C10 C15 N8 119.0(6) . . ?
C14 C15 N8 115.3(6) . . ?
C14 C15 C10 125.8(6) . . ?
C4 C3 C7 104.8(6) . . ?
C2 C3 C4 118.3(6) . . ?
C2 C3 C7 137.0(6) . . ?
C12 C13 N10 120.0(6) . . ?
C12 C13 C14 121.7(6) . . ?
C14 C13 N10 118.3(6) . . ?
C10 C11 N9 120.1(6) . . ?
C12 C11 N9 116.3(6) . . ?
C12 C11 C10 123.6(6) . . ?
N6 C8 N3 116.1(5) . . ?
N6 C8 N5 127.8(6) . . ?
N5 C8 N3 116.1(6) . . ?
C15 C10 C11 113.0(6) . . ?
C15 C10 C9 122.5(6) . . ?
C11 C10 C9 124.5(6) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 C13 119.1(6) . . ?
C11 C12 H12 120.5 . . ?
C6 C1 H1 121.6 . . ?
C2 C1 C6 116.9(6) . . ?
C2 C1 H1 121.6 . . ?
C3 C2 N1 119.7(6) . . ?
C1 C2 N1 119.0(6) . . ?
C1 C2 C3 121.3(6) . . ?
N7 C9 C10 125.3(7) . . ?
N7 C9 H9 117.4 . . ?
C10 C9 H9 117.4 . . ?
C15 C14 C13 116.8(6) . . ?
C15 C14 H14 121.6 . . ?
C13 C14 H14 121.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.762(4)
2 0.238(4)

