# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_dm17410_0m
_database_code_depnum_ccdc_archive 'CCDC 2125442'
loop_
_audit_author_name
_audit_author_address
'Shen Qiao'
;North university of China
China
;
_audit_update_record             
;
2021-12-01 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H5 N7 O10'
_chemical_formula_weight         371.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   6.4839(5)
_cell_length_b                   10.5895(8)
_cell_length_c                   20.8436(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1431.15(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5404
_cell_measurement_theta_min      5.484
_cell_measurement_theta_max      54.587

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.159
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6963
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10415
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.954
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2793
_reflns_number_gt                2621
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0359P)²+0.2343P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.045(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1024 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.1(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2793
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0722
_refine_ls_wR_factor_gt          0.0703
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3502(3) 0.41626(17) 0.87198(9) 0.0448(4) Uani 1 1 d . . . . .
N2 N 0.6652(3) 0.3450(2) 0.66189(10) 0.0531(5) Uani 1 1 d . . . . .
N3 N 0.0158(3) 0.13434(19) 0.71755(9) 0.0500(5) Uani 1 1 d . . . . .
N4 N 0.6763(3) 0.1357(2) 0.88924(10) 0.0535(5) Uani 1 1 d . . . . .
N5 N 1.2744(4) -0.0102(2) 1.00776(9) 0.0551(6) Uani 1 1 d . . . . .
N6 N 1.0814(3) -0.00462(18) 0.97501(9) 0.0435(4) Uani 1 1 d . . . . .
N7 N 0.7859(4) -0.0658(2) 0.93529(11) 0.0582(5) Uani 1 1 d . . . . .
O1 O 0.2449(3) 0.37065(19) 0.91393(8) 0.0615(5) Uani 1 1 d . . . . .
O2 O 0.4689(3) 0.50396(17) 0.87977(9) 0.0652(5) Uani 1 1 d . . . . .
O3 O 0.8066(3) 0.4137(2) 0.67946(10) 0.0713(6) Uani 1 1 d . . . . .
O4 O 0.6578(4) 0.2922(2) 0.61012(9) 0.0744(6) Uani 1 1 d . . . . .
O5 O 0.0410(4) 0.0650(2) 0.67172(10) 0.0877(7) Uani 1 1 d . . . . .
O6 O -0.1365(3) 0.1331(2) 0.75120(10) 0.0689(5) Uani 1 1 d . . . . .
O7 O 0.7186(3) 0.24789(17) 0.88344(10) 0.0712(6) Uani 1 1 d . . . . .
O8 O 0.5203(3) 0.0863(2) 0.86776(12) 0.0802(6) Uani 1 1 d . . . . .
O9 O 1.3717(3) 0.0859(2) 1.00765(12) 0.0804(6) Uani 1 1 d . . . . .
O10 O 1.3139(4) -0.1111(2) 1.03167(9) 0.0766(6) Uani 1 1 d . . . . .
C1 C 0.3410(3) 0.35958(19) 0.80759(9) 0.0371(4) Uani 1 1 d . . . . .
C2 C 0.4993(3) 0.38359(19) 0.76562(10) 0.0407(5) Uani 1 1 d . . . . .
H2 H 0.6065 0.4379 0.7764 0.049 Uiso 1 1 calc R U . . .
C3 C 0.4932(3) 0.3242(2) 0.70698(10) 0.0405(5) Uani 1 1 d . . . . .
C4 C 0.3370(4) 0.2431(2) 0.68910(10) 0.0418(5) Uani 1 1 d . . . . .
H4 H 0.3356 0.2038 0.6492 0.050 Uiso 1 1 calc R U . . .
C5 C 0.1824(3) 0.22333(19) 0.73380(10) 0.0392(5) Uani 1 1 d . . . . .
C6 C 0.1791(3) 0.28012(18) 0.79328(9) 0.0373(4) Uani 1 1 d . . . . .
H6 H 0.0729 0.2655 0.8223 0.045 Uiso 1 1 calc R U . . .
C7 C 1.0022(4) 0.1010(2) 0.94701(10) 0.0419(5) Uani 1 1 d . . . . .
H7A H 1.0586 0.1817 0.9449 0.050 Uiso 1 1 calc R U . . .
C8 C 0.8219(4) 0.0592(2) 0.92321(10) 0.0441(5) Uani 1 1 d . . . . .
C9 C 0.9466(4) -0.1023(2) 0.96707(13) 0.0574(7) Uani 1 1 d . . . . .
H9 H 0.9674 -0.1838 0.9824 0.069 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 O1 1.210(3) . ?
N1 O2 1.217(2) . ?
N1 C1 1.472(3) . ?
N2 O4 1.216(3) . ?
N2 O3 1.226(3) . ?
N2 C3 1.475(3) . ?
N3 O6 1.211(3) . ?
N3 O5 1.216(3) . ?
N3 C5 1.473(3) . ?
N4 O8 1.224(3) . ?
N4 O7 1.225(3) . ?
N4 C8 1.432(3) . ?
N5 O9 1.197(3) . ?
N5 O10 1.207(3) . ?
N5 N6 1.427(3) . ?
N6 C7 1.362(3) . ?
N6 C9 1.364(3) . ?
N7 C9 1.294(3) . ?
N7 C8 1.368(3) . ?
O1 O8 3.631(3) . ?
C1 C2 1.372(3) . ?
C1 C6 1.378(3) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(3) . ?
C4 C5 1.384(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.345(3) . ?
C7 H7A 0.9300 . ?
C9 H9 0.9300 . ?

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
O1 N1 O2 124.4(2) . . ?
O1 N1 C1 118.26(18) . . ?
O2 N1 C1 117.29(19) . . ?
O4 N2 O3 124.5(2) . . ?
O4 N2 C3 117.8(2) . . ?
O3 N2 C3 117.6(2) . . ?
O6 N3 O5 123.9(2) . . ?
O6 N3 C5 118.16(18) . . ?
O5 N3 C5 118.0(2) . . ?
O8 N4 O7 124.3(2) . . ?
O8 N4 C8 118.9(2) . . ?
O7 N4 C8 116.7(2) . . ?
O9 N5 O10 129.9(2) . . ?
O9 N5 N6 115.2(2) . . ?
O10 N5 N6 114.9(2) . . ?
C7 N6 C9 109.22(19) . . ?
C7 N6 N5 124.7(2) . . ?
C9 N6 N5 126.1(2) . . ?
C9 N7 C8 104.2(2) . . ?
N1 O1 O8 82.07(13) . . ?
N4 O8 O1 87.39(15) . . ?
C2 C1 C6 123.02(19) . . ?
C2 C1 N1 118.39(19) . . ?
C6 C1 N1 118.52(18) . . ?
C1 C2 C3 117.4(2) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C2 C3 C4 123.1(2) . . ?
C2 C3 N2 118.5(2) . . ?
C4 C3 N2 118.4(2) . . ?
C3 C4 C5 116.35(19) . . ?
C3 C4 H4 121.8 . . ?
C5 C4 H4 121.8 . . ?
C6 C5 C4 123.42(19) . . ?
C6 C5 N3 118.33(19) . . ?
C4 C5 N3 118.23(18) . . ?
C1 C6 C5 116.70(19) . . ?
C1 C6 H6 121.7 . . ?
C5 C6 H6 121.7 . . ?
C8 C7 N6 102.44(19) . . ?
C8 C7 H7A 128.8 . . ?
N6 C7 H7A 128.8 . . ?
C7 C8 N7 113.5(2) . . ?
C7 C8 N4 124.7(2) . . ?
N7 C8 N4 121.7(2) . . ?
N7 C9 N6 110.6(2) . . ?
N7 C9 H9 124.7 . . ?
N6 C9 H9 124.7 . . ?

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
O9 N5 N6 C7 -2.5(3) . . . . ?
O10 N5 N6 C7 177.1(2) . . . . ?
O9 N5 N6 C9 178.0(2) . . . . ?
O10 N5 N6 C9 -2.4(3) . . . . ?
O2 N1 O1 O8 -122.2(2) . . . . ?
C1 N1 O1 O8 55.45(17) . . . . ?
O7 N4 O8 O1 -38.9(3) . . . . ?
C8 N4 O8 O1 141.56(19) . . . . ?
O1 N1 C1 C2 -160.7(2) . . . . ?
O2 N1 C1 C2 17.1(3) . . . . ?
O1 N1 C1 C6 16.2(3) . . . . ?
O2 N1 C1 C6 -166.0(2) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
N1 C1 C2 C3 176.56(18) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C1 C2 C3 N2 -177.91(18) . . . . ?
O4 N2 C3 C2 -179.8(2) . . . . ?
O3 N2 C3 C2 0.7(3) . . . . ?
O4 N2 C3 C4 2.2(3) . . . . ?
O3 N2 C3 C4 -177.3(2) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
N2 C3 C4 C5 177.92(18) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C3 C4 C5 N3 -178.13(18) . . . . ?
O6 N3 C5 C6 14.1(3) . . . . ?
O5 N3 C5 C6 -164.7(2) . . . . ?
O6 N3 C5 C4 -167.5(2) . . . . ?
O5 N3 C5 C4 13.7(3) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
N1 C1 C6 C5 -176.38(18) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
N3 C5 C6 C1 177.95(18) . . . . ?
C9 N6 C7 C8 -0.4(2) . . . . ?
N5 N6 C7 C8 -179.87(19) . . . . ?
N6 C7 C8 N7 0.3(2) . . . . ?
N6 C7 C8 N4 179.2(2) . . . . ?
C9 N7 C8 C7 -0.1(3) . . . . ?
C9 N7 C8 N4 -179.1(2) . . . . ?
O8 N4 C8 C7 177.4(2) . . . . ?
O7 N4 C8 C7 -2.1(3) . . . . ?
O8 N4 C8 N7 -3.7(3) . . . . ?
O7 N4 C8 N7 176.7(2) . . . . ?
C8 N7 C9 N6 -0.2(3) . . . . ?
C7 N6 C9 N7 0.4(3) . . . . ?
N5 N6 C9 N7 179.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9 O10 0.93 2.41 3.154(3) 137.4 4_447
C7 H7A O1 0.93 2.43 3.332(3) 165.1 1_655
C6 H6 O7 0.93 2.63 3.544(3) 166.6 1_455
C4 H4 O2 0.93 2.54 3.172(3) 125.5 3_646

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.026

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_dm17411_0m
_database_code_depnum_ccdc_archive 'CCDC 2125443'
loop_
_audit_author_name
_audit_author_address
'Shen Qiao'
;North university of China
China
;
_audit_update_record             
;
2021-12-01 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H6 N8 O10'
_chemical_formula_weight         386.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   6.7852(17)
_cell_length_b                   11.054(3)
_cell_length_c                   20.043(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1503.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1715
_cell_measurement_theta_min      5.487
_cell_measurement_theta_max      42.761

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.157
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5757
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10367
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.032
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2796
_reflns_number_gt                1819
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0566P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 623 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   1.2(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2796
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6411(5) 0.1360(4) 0.1756(2) 0.0609(10) Uani 1 1 d . . . . .
N2 N 0.2895(6) 0.0539(4) 0.38448(19) 0.0588(10) Uani 1 1 d . . . . .
N3 N 0.0419(6) 0.3627(4) 0.2289(2) 0.0620(11) Uani 1 1 d . . . . .
N4 N 0.1953(5) 1.0447(3) 0.08781(18) 0.0572(10) Uani 1 1 d . . . . .
N5 N 0.0184(6) 0.8807(4) 0.0555(2) 0.0607(11) Uani 1 1 d . . . . .
N6 N -0.0745(5) 0.9827(4) 0.03627(18) 0.0538(10) Uani 1 1 d . . . . .
N7 N -0.0191(6) 1.2019(4) 0.0438(2) 0.0599(10) Uani 1 1 d . . . . .
N8 N 0.3222(6) 0.8446(4) 0.1121(2) 0.0688(11) Uani 1 1 d . . . . .
O1 O 0.6403(5) 0.1869(4) 0.12201(19) 0.0846(12) Uani 1 1 d . . . . .
O2 O 0.7672(5) 0.0644(4) 0.19275(19) 0.0907(13) Uani 1 1 d . . . . .
O3 O 0.4013(5) -0.0309(3) 0.39349(18) 0.0803(11) Uani 1 1 d . . . . .
O4 O 0.1683(6) 0.0884(3) 0.42465(17) 0.0813(11) Uani 1 1 d . . . . .
O5 O -0.1177(5) 0.3598(4) 0.2577(2) 0.0877(12) Uani 1 1 d . . . . .
O6 O 0.0886(5) 0.4371(3) 0.18731(19) 0.0771(11) Uani 1 1 d . . . . .
O7 O -0.1188(6) 1.2228(3) -0.0049(2) 0.0777(11) Uani 1 1 d . . . . .
O8 O 0.0398(6) 1.2775(3) 0.0839(2) 0.0840(12) Uani 1 1 d . . . . .
O9 O 0.4672(6) 0.8903(4) 0.1395(2) 0.0934(13) Uani 1 1 d . . . . .
O10 O 0.2921(6) 0.7362(4) 0.1084(2) 0.0925(12) Uani 1 1 d . . . . .
C1 C 0.4749(6) 0.1606(4) 0.2215(2) 0.0474(10) Uani 1 1 d . . . . .
C2 C 0.4624(6) 0.0949(4) 0.2793(2) 0.0478(10) Uani 1 1 d . . . . .
H2 H 0.5558 0.0366 0.2902 0.057 Uiso 1 1 calc R U . . .
C3 C 0.3044(6) 0.1196(4) 0.3205(2) 0.0455(10) Uani 1 1 d . . . . .
C4 C 0.1648(6) 0.2045(4) 0.3053(2) 0.0491(11) Uani 1 1 d . . . . .
H4 H 0.0581 0.2185 0.3334 0.059 Uiso 1 1 calc R U . . .
C5 C 0.1878(6) 0.2685(4) 0.2468(2) 0.0490(11) Uani 1 1 d . . . . .
C6 C 0.3423(6) 0.2484(4) 0.2038(2) 0.0512(11) Uani 1 1 d . . . . .
H6 H 0.3561 0.2923 0.1645 0.061 Uiso 1 1 calc R U . . .
C7 C 0.0353(7) 1.0777(4) 0.0560(2) 0.0514(11) Uani 1 1 d . . . . .
C8 C 0.1769(7) 0.9251(4) 0.0852(2) 0.0543(11) Uani 1 1 d . . . . .
C9 C -0.2648(8) 0.9758(5) 0.0012(3) 0.0724(14) Uani 1 1 d . . . . .
H9A H -0.2485 1.0029 -0.0439 0.109 Uiso 1 1 calc R U . . .
H9B H -0.3592 1.0263 0.0235 0.109 Uiso 1 1 calc R U . . .
H9C H -0.3107 0.8936 0.0012 0.109 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 O1 1.212(5) . ?
N1 O2 1.215(5) . ?
N1 C1 1.480(5) . ?
N2 O4 1.212(5) . ?
N2 O3 1.219(5) . ?
N2 C3 1.477(5) . ?
N3 O6 1.214(5) . ?
N3 O5 1.227(5) . ?
N3 C5 1.481(6) . ?
N4 C7 1.311(5) . ?
N4 C8 1.329(5) . ?
N5 C8 1.324(6) . ?
N5 N6 1.347(5) . ?
N6 C7 1.347(5) . ?
N6 C9 1.472(6) . ?
N7 O7 1.210(5) . ?
N7 O8 1.226(5) . ?
N7 C7 1.443(6) . ?
N8 O10 1.217(5) . ?
N8 O9 1.235(5) . ?
N8 C8 1.434(6) . ?
C1 C6 1.370(6) . ?
C1 C2 1.370(6) . ?
C2 C3 1.381(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(6) . ?
C4 C5 1.378(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(6) . ?
C6 H6 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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
O1 N1 O2 123.8(4) . . ?
O1 N1 C1 117.5(4) . . ?
O2 N1 C1 118.7(4) . . ?
O4 N2 O3 124.5(4) . . ?
O4 N2 C3 117.9(4) . . ?
O3 N2 C3 117.6(4) . . ?
O6 N3 O5 124.8(4) . . ?
O6 N3 C5 117.9(4) . . ?
O5 N3 C5 117.3(5) . . ?
C7 N4 C8 100.4(4) . . ?
C8 N5 N6 101.5(4) . . ?
N5 N6 C7 108.0(3) . . ?
N5 N6 C9 120.2(4) . . ?
C7 N6 C9 131.7(4) . . ?
O7 N7 O8 125.5(4) . . ?
O7 N7 C7 117.5(4) . . ?
O8 N7 C7 117.0(4) . . ?
O10 N8 O9 124.3(5) . . ?
O10 N8 C8 118.2(4) . . ?
O9 N8 C8 117.5(4) . . ?
C6 C1 C2 123.6(4) . . ?
C6 C1 N1 118.0(4) . . ?
C2 C1 N1 118.4(4) . . ?
C1 C2 C3 116.7(4) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 H2 121.6 . . ?
C4 C3 C2 122.6(4) . . ?
C4 C3 N2 118.9(4) . . ?
C2 C3 N2 118.4(4) . . ?
C3 C4 C5 117.7(4) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C6 C5 C4 122.4(4) . . ?
C6 C5 N3 118.1(4) . . ?
C4 C5 N3 119.4(4) . . ?
C1 C6 C5 116.9(4) . . ?
C1 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
N4 C7 N6 112.6(4) . . ?
N4 C7 N7 124.0(4) . . ?
N6 C7 N7 123.4(4) . . ?
N5 C8 N4 117.5(4) . . ?
N5 C8 N8 119.9(4) . . ?
N4 C8 N8 122.6(4) . . ?
N6 C9 H9A 109.5 . . ?
N6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N6 C9 H9C 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
C8 N5 N6 C7 -0.1(4) . . . . ?
C8 N5 N6 C9 -179.0(4) . . . . ?
O1 N1 C1 C6 -6.7(6) . . . . ?
O2 N1 C1 C6 175.0(4) . . . . ?
O1 N1 C1 C2 173.5(4) . . . . ?
O2 N1 C1 C2 -4.8(6) . . . . ?
C6 C1 C2 C3 0.9(6) . . . . ?
N1 C1 C2 C3 -179.4(4) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C1 C2 C3 N2 -177.8(4) . . . . ?
O4 N2 C3 C4 -9.1(6) . . . . ?
O3 N2 C3 C4 171.6(4) . . . . ?
O4 N2 C3 C2 169.1(4) . . . . ?
O3 N2 C3 C2 -10.2(5) . . . . ?
C2 C3 C4 C5 -1.3(6) . . . . ?
N2 C3 C4 C5 176.9(4) . . . . ?
C3 C4 C5 C6 1.1(6) . . . . ?
C3 C4 C5 N3 -179.0(4) . . . . ?
O6 N3 C5 C6 -18.0(6) . . . . ?
O5 N3 C5 C6 162.3(4) . . . . ?
O6 N3 C5 C4 162.1(4) . . . . ?
O5 N3 C5 C4 -17.6(6) . . . . ?
C2 C1 C6 C5 -1.1(6) . . . . ?
N1 C1 C6 C5 179.2(4) . . . . ?
C4 C5 C6 C1 0.1(6) . . . . ?
N3 C5 C6 C1 -179.9(4) . . . . ?
C8 N4 C7 N6 0.8(5) . . . . ?
C8 N4 C7 N7 -179.6(4) . . . . ?
N5 N6 C7 N4 -0.5(5) . . . . ?
C9 N6 C7 N4 178.3(4) . . . . ?
N5 N6 C7 N7 179.9(4) . . . . ?
C9 N6 C7 N7 -1.3(7) . . . . ?
O7 N7 C7 N4 152.1(4) . . . . ?
O8 N7 C7 N4 -27.9(6) . . . . ?
O7 N7 C7 N6 -28.3(6) . . . . ?
O8 N7 C7 N6 151.6(4) . . . . ?
N6 N5 C8 N4 0.7(5) . . . . ?
N6 N5 C8 N8 -178.4(4) . . . . ?
C7 N4 C8 N5 -0.9(5) . . . . ?
C7 N4 C8 N8 178.1(4) . . . . ?
O10 N8 C8 N5 -2.0(7) . . . . ?
O9 N8 C8 N5 -179.8(4) . . . . ?
O10 N8 C8 N4 179.0(5) . . . . ?
O9 N8 C8 N4 1.2(7) . . . . ?

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-4



