# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xmx-4
_database_code_depnum_ccdc_archive 'CCDC 1918899'
loop_
_audit_author_name
_audit_author_address
'hualin xiong'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-02-03 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_audit_creation_date             2023-02-03
_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         'C10 H4 N16 O8'
_chemical_formula_sum            'C10 H4 N16 O8'
_chemical_formula_weight         476.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0035 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 0.0065 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0116 0.0061 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.7356(16)
_cell_length_b                   10.1583(16)
_cell_length_c                   15.310(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1669.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1467
_cell_measurement_temperature    173
_cell_measurement_theta_max      21.32
_cell_measurement_theta_min      3.06
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0539 before and 0.0381 after correction. The Ratio of minimum to maximum transmission is 0.9028. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.895
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12929
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.459
_diffrn_reflns_theta_min         2.661
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1300
_reflns_number_total             1726
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.288
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         1726
_refine_ls_number_restraints     335
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      0.982
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0621P)²+1.3833P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1331
_refine_special_details          ?
_olex2_refinement_description    
;
1. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(O2) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(O4A) \\sim Ueq, Uanis(O4) \\sim
Ueq, Uanis(O7) \\sim Ueq, Uanis(O7A) \\sim Ueq, Uanis(O3A) \\sim Ueq, Uanis(O3)
\\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(O1A) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
3. Others
 Fixed Sof: O1(0.815) O3(0.815) O4(0.53) O7(0.53) O2(0.05) O5(0.05) O4A(0.42)
 O7A(0.42) O1A(0.185) O3A(0.185)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5529(7) 0.8339(7) 0.3155(5) 0.0337(10) Uani 0.815 1 d . U P A 1
N6 N 0.84794(18) 0.72609(18) 0.46651(14) 0.0233(5) Uani 1 1 d . U . . .
N7 N 0.78249(17) 0.51878(18) 0.43801(14) 0.0226(5) Uani 1 1 d . U . . .
N8 N 0.99336(18) 0.56153(18) 0.49836(14) 0.0233(5) Uani 1 1 d . U . . .
N5 N 0.73233(18) 0.7278(2) 0.43332(14) 0.0248(5) Uani 1 1 d . U . . .
N4 N 0.52232(19) 0.4512(2) 0.41235(15) 0.0291(5) Uani 1 1 d . U . . .
N1 N 0.4862(2) 0.7459(2) 0.29041(15) 0.0344(6) Uani 1 1 d . U . . .
N3 N 0.40363(19) 0.4332(2) 0.38815(15) 0.0345(6) Uani 1 1 d . U . . .
O3 O 0.4316(4) 0.7456(4) 0.2190(3) 0.0477(9) Uani 0.815 1 d . U P A 1
N2 N 0.2490(2) 0.5576(3) 0.31408(18) 0.0445(7) Uani 1 1 d . U . . .
C5 C 0.8746(2) 0.5983(2) 0.46772(16) 0.0217(5) Uani 1 1 d . U . . .
C4 C 0.6946(2) 0.6049(2) 0.41658(17) 0.0225(5) Uani 1 1 d . U . . .
C3 C 0.5695(2) 0.5680(2) 0.38759(16) 0.0245(5) Uani 1 1 d . U . . .
C2 C 0.4752(2) 0.6285(2) 0.34161(17) 0.0265(6) Uani 1 1 d . U . . .
C1 C 0.3764(2) 0.5400(3) 0.34488(18) 0.0306(6) Uani 1 1 d . U . . .
O4 O 0.2178(9) 0.6631(11) 0.2882(5) 0.055(2) Uani 0.53 1 d . U P B 1
O7 O 0.1782(6) 0.4676(8) 0.3256(5) 0.079(2) Uani 0.53 1 d . U P B 1
H4 H 0.564(3) 0.383(3) 0.443(2) 0.056(10) Uiso 1 1 d . . . . .
H5 H 0.696(3) 0.802(3) 0.4293(19) 0.034(8) Uiso 1 1 d . . . . .
O2 O 0.248(4) 0.554(5) 0.231(3) 0.050(7) Uani 0.05 1 d . U P B 3
O5 O 0.175(4) 0.578(6) 0.364(4) 0.056(7) Uani 0.05 1 d . U P B 3
O4A O 0.2053(14) 0.6630(17) 0.3241(8) 0.079(4) Uani 0.42 1 d . U P B 2
O7A O 0.2027(8) 0.4586(10) 0.2757(6) 0.069(2) Uani 0.42 1 d . U P B 2
O1A O 0.572(4) 0.822(4) 0.323(3) 0.057(8) Uani 0.185 1 d . U P A 2
O3A O 0.400(2) 0.781(2) 0.2430(15) 0.072(6) Uani 0.185 1 d . U 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
O1 N1 1.208(8) . ?
N6 N5 1.341(3) . ?
N6 C5 1.329(3) . ?
N7 C5 1.356(3) . ?
N7 C4 1.328(3) . ?
N8 N8 1.259(4) 5_766 ?
N8 C5 1.409(3) . ?
N5 C4 1.337(3) . ?
N4 N3 1.340(3) . ?
N4 C3 1.345(3) . ?
N1 O3 1.240(4) . ?
N1 C2 1.432(3) . ?
N1 O1A 1.30(4) . ?
N1 O3A 1.23(2) . ?
N3 C1 1.304(4) . ?
N2 C1 1.458(3) . ?
N2 O4 1.191(11) . ?
N2 O7 1.201(7) . ?
N2 O2 1.27(5) . ?
N2 O5 1.12(5) . ?
N2 O4A 1.179(17) . ?
N2 O7A 1.267(9) . ?
C4 C3 1.464(3) . ?
C3 C2 1.378(3) . ?
C2 C1 1.391(4) . ?

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
C5 N6 N5 102.56(18) . . ?
C4 N7 C5 102.02(18) . . ?
N8 N8 C5 112.3(2) 5_766 . ?
C4 N5 N6 109.89(19) . . ?
N3 N4 C3 113.6(2) . . ?
O1 N1 O3 124.2(5) . . ?
O1 N1 C2 119.4(4) . . ?
O3 N1 C2 116.2(3) . . ?
O1A N1 C2 110.4(18) . . ?
O3A N1 C2 119.9(12) . . ?
O3A N1 O1A 126(2) . . ?
C1 N3 N4 103.9(2) . . ?
O4 N2 C1 118.8(5) . . ?
O4 N2 O7 123.7(6) . . ?
O7 N2 C1 116.9(4) . . ?
O2 N2 C1 109(2) . . ?
O5 N2 C1 118(3) . . ?
O5 N2 O2 133(3) . . ?
O4A N2 C1 116.3(8) . . ?
O4A N2 O7A 128.7(9) . . ?
O7A N2 C1 114.9(5) . . ?
N6 C5 N7 114.8(2) . . ?
N6 C5 N8 117.3(2) . . ?
N7 C5 N8 127.9(2) . . ?
N7 C4 N5 110.7(2) . . ?
N7 C4 C3 123.9(2) . . ?
N5 C4 C3 125.1(2) . . ?
N4 C3 C4 119.1(2) . . ?
N4 C3 C2 105.1(2) . . ?
C2 C3 C4 135.6(2) . . ?
C3 C2 N1 126.2(2) . . ?
C3 C2 C1 104.7(2) . . ?
C1 C2 N1 128.4(2) . . ?
N3 C1 N2 118.4(2) . . ?
N3 C1 C2 112.7(2) . . ?
C2 C1 N2 128.6(2) . . ?


_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 1918906'
loop_
_audit_author_name
_audit_author_address
'hualin xiong'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-02-03 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_audit_creation_date             2018-12-24
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H3 N9 O6, 1.5(C4 H8 O2)'
_chemical_formula_sum            'C11 H15 N9 O9'
_chemical_formula_weight         417.32
_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'

_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                   8.7665(19)
_cell_length_b                   10.158(2)
_cell_length_c                   10.814(2)
_cell_angle_alpha                114.184(3)
_cell_angle_beta                 98.141(3)
_cell_angle_gamma                99.022(3)
_cell_volume                     844.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1545
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.24
_cell_measurement_theta_min      2.26
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9753
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.018
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_min         2.121
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD 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                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2061
_reflns_number_total             2948
_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       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         2948
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.051
_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)+(0.0263P)²+0.3524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0916
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H6A(0.037) H6B(0.037) H7A(0.036) H7B(0.036) H8A(0.032) H8B(0.032)
 H9A(0.031) H9B(0.031) H10A(0.034) H10B(0.034) H11A(0.034) H11B(0.034)
 H2(0.025) H4(0.027) H6(0.025)
 Fixed X: H6A(-0.1334) H6B(0.0214) H7A(0.1001) H7B(-0.0759) H8A(1.0097)
 H8B(0.8455) H9A(0.886) H9B(1.0538) H10A(1.0539) H10B(0.8864) H11A(0.8461)
 H11B(1.011)
 Fixed Y: H6A(0.4357) H6B(0.3925) H7A(0.3419) H7B(0.2444) H8A(0.8294)
 H8B(0.7369) H9A(0.9868) H9B(0.9837) H10A(0.8282) H10B(0.7365) H11A(0.5875)
 H11B(0.5799)
 Fixed Z: H6A(0.0949) H6B(0.1507) H7A(-0.0584) H7B(-0.0905) H8A(0.7907)
 H8B(0.679) H9A(0.7238) H9B(0.6813) H10A(0.436) H10B(0.329) H11A(0.444)
 H11B(0.3967)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.4456(3) 0.8414(3) 0.3234(2) 0.0195(6) Uani 1 1 d . . . . .
C2 C 0.5184(3) 1.0154(3) 0.2746(2) 0.0186(6) Uani 1 1 d . . . . .
C3 C 0.4860(3) 1.2816(3) 0.1313(2) 0.0186(6) Uani 1 1 d . . . . .
C4 C 0.4146(3) 1.1459(3) 0.1266(2) 0.0187(6) Uani 1 1 d . . . . .
C5 C 0.5215(3) 1.1258(3) 0.2208(2) 0.0189(6) Uani 1 1 d . . . . .
C6 C -0.0210(3) 0.4369(3) 0.0910(3) 0.0312(7) Uani 1 1 d . . . . .
H6A H -0.1334 0.4357 0.0949 0.037 Uiso 1 1 calc R U . . .
H6B H 0.0214 0.3925 0.1507 0.037 Uiso 1 1 calc R U . . .
C7 C -0.0113(3) 0.3469(3) -0.0555(3) 0.0303(7) Uani 1 1 d . . . . .
H7A H 0.1001 0.3419 -0.0584 0.036 Uiso 1 1 calc R U . . .
H7B H -0.0759 0.2444 -0.0905 0.036 Uiso 1 1 calc R U . . .
C8 C 0.9541(3) 0.7936(3) 0.6925(2) 0.0263(6) Uani 1 1 d . . . . .
H8A H 1.0097 0.8294 0.7907 0.032 Uiso 1 1 calc R U . . .
H8B H 0.8455 0.7369 0.6790 0.032 Uiso 1 1 calc R U . . .
C9 C 0.9453(3) 0.9234(3) 0.6622(2) 0.0256(6) Uani 1 1 d . . . . .
H9A H 0.8860 0.9868 0.7238 0.031 Uiso 1 1 calc R U . . .
H9B H 1.0538 0.9837 0.6813 0.031 Uiso 1 1 calc R U . . .
C10 C 0.9455(3) 0.7738(3) 0.4265(3) 0.0283(7) Uani 1 1 d . . . . .
H10A H 1.0539 0.8282 0.4360 0.034 Uiso 1 1 calc R U . . .
H10B H 0.8864 0.7365 0.3290 0.034 Uiso 1 1 calc R U . . .
C11 C 0.9546(3) 0.6458(3) 0.4595(2) 0.0287(7) Uani 1 1 d . . . . .
H11A H 0.8461 0.5875 0.4440 0.034 Uiso 1 1 calc R U . . .
H11B H 1.0110 0.5799 0.3967 0.034 Uiso 1 1 calc R U . . .
N1 N 0.6485(2) 1.0189(2) 0.3554(2) 0.0214(5) Uani 1 1 d . . . . .
N2 N 0.5988(2) 0.9040(2) 0.3864(2) 0.0210(5) Uani 1 1 d D . . . .
H2 H 0.670(3) 0.879(3) 0.438(2) 0.025 Uiso 1 1 d D U . . .
N3 N 0.3880(2) 0.9094(2) 0.25238(19) 0.0192(5) Uani 1 1 d . . . . .
N4 N 0.3494(3) 0.7240(2) 0.3290(2) 0.0226(5) Uani 1 1 d D . . . .
H4 H 0.255(2) 0.676(3) 0.267(2) 0.027 Uiso 1 1 d D U . . .
N5 N 0.4016(3) 0.6477(2) 0.3973(2) 0.0282(6) Uani 1 1 d . . . . .
N6 N 0.6449(2) 1.2456(2) 0.2711(2) 0.0212(5) Uani 1 1 d D . . . .
H6 H 0.738(2) 1.257(3) 0.327(2) 0.025 Uiso 1 1 d D U . . .
N7 N 0.6262(2) 1.3424(2) 0.2170(2) 0.0225(5) Uani 1 1 d . . . . .
N8 N 0.4251(2) 1.3522(2) 0.0486(2) 0.0231(5) Uani 1 1 d . . . . .
N9 N 0.2632(3) 1.0508(2) 0.04126(19) 0.0212(5) Uani 1 1 d . . . . .
O1 O 0.3045(2) 0.5368(2) 0.3813(2) 0.0388(5) Uani 1 1 d . . . . .
O2 O 0.5370(2) 0.6939(2) 0.46994(18) 0.0331(5) Uani 1 1 d . . . . .
O3 O 0.4309(2) 1.4848(2) 0.10829(18) 0.0333(5) Uani 1 1 d . . . . .
O4 O 0.3700(2) 1.27219(19) -0.07617(17) 0.0294(5) Uani 1 1 d . . . . .
O5 O 0.1598(2) 1.1118(2) 0.01704(18) 0.0315(5) Uani 1 1 d . . . . .
O6 O 0.2474(2) 0.91634(19) -0.00402(17) 0.0282(5) Uani 1 1 d . . . . .
O7 O 0.0679(2) 0.58772(18) 0.14285(16) 0.0262(4) Uani 1 1 d . . . . .
O8 O 1.0371(2) 0.69817(18) 0.60221(16) 0.0250(4) Uani 1 1 d . . . . .
O9 O 0.8672(2) 0.87329(19) 0.51871(17) 0.0264(4) 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 N2 1.338(3) . ?
C1 N3 1.325(3) . ?
C1 N4 1.377(3) . ?
C2 C5 1.458(3) . ?
C2 N1 1.321(3) . ?
C2 N3 1.359(3) . ?
C3 C4 1.399(3) . ?
C3 N7 1.312(3) . ?
C3 N8 1.453(3) . ?
C4 C5 1.384(3) . ?
C4 N9 1.438(3) . ?
C5 N6 1.351(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.493(4) . ?
C6 O7 1.438(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 O7 1.437(3) 2_565 ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.493(3) . ?
C8 O8 1.439(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 O9 1.442(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.493(3) . ?
C10 O9 1.439(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 O8 1.442(3) . ?
N1 N2 1.367(3) . ?
N2 H2 0.909(18) . ?
N4 H4 0.901(18) . ?
N4 N5 1.356(3) . ?
N5 O1 1.233(3) . ?
N5 O2 1.227(3) . ?
N6 H6 0.899(18) . ?
N6 N7 1.353(3) . ?
N8 O3 1.221(3) . ?
N8 O4 1.228(2) . ?
N9 O5 1.231(3) . ?
N9 O6 1.224(3) . ?
O7 C7 1.437(3) 2_565 ?

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
N2 C1 N4 127.7(2) . . ?
N3 C1 N2 111.7(2) . . ?
N3 C1 N4 120.6(2) . . ?
N1 C2 C5 119.2(2) . . ?
N1 C2 N3 115.9(2) . . ?
N3 C2 C5 124.9(2) . . ?
C4 C3 N8 127.2(2) . . ?
N7 C3 C4 112.9(2) . . ?
N7 C3 N8 119.8(2) . . ?
C3 C4 N9 126.4(2) . . ?
C5 C4 C3 104.8(2) . . ?
C5 C4 N9 128.8(2) . . ?
C4 C5 C2 134.0(2) . . ?
N6 C5 C2 120.8(2) . . ?
N6 C5 C4 105.0(2) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
O7 C6 H6A 109.5 . . ?
O7 C6 H6B 109.5 . . ?
O7 C6 C7 110.7(2) . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
O7 C7 C6 110.3(2) 2_565 . ?
O7 C7 H7A 109.6 2_565 . ?
O7 C7 H7B 109.6 2_565 . ?
H8A C8 H8B 108.1 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
O8 C8 H8A 109.5 . . ?
O8 C8 H8B 109.5 . . ?
O8 C8 C9 110.6(2) . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
O9 C9 C8 110.3(2) . . ?
O9 C9 H9A 109.6 . . ?
O9 C9 H9B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
O9 C10 H10A 109.5 . . ?
O9 C10 H10B 109.5 . . ?
O9 C10 C11 110.7(2) . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
O8 C11 C10 110.3(2) . . ?
O8 C11 H11A 109.6 . . ?
O8 C11 H11B 109.6 . . ?
C2 N1 N2 102.13(19) . . ?
C1 N2 N1 108.9(2) . . ?
C1 N2 H2 131.4(16) . . ?
N1 N2 H2 119.6(16) . . ?
C1 N3 C2 101.41(19) . . ?
C1 N4 H4 120.3(16) . . ?
N5 N4 C1 123.5(2) . . ?
N5 N4 H4 114.0(16) . . ?
O1 N5 N4 115.4(2) . . ?
O2 N5 N4 118.8(2) . . ?
O2 N5 O1 125.7(2) . . ?
C5 N6 H6 124.9(16) . . ?
C5 N6 N7 113.9(2) . . ?
N7 N6 H6 120.8(16) . . ?
C3 N7 N6 103.41(19) . . ?
O3 N8 C3 117.9(2) . . ?
O3 N8 O4 125.4(2) . . ?
O4 N8 C3 116.8(2) . . ?
O5 N9 C4 116.9(2) . . ?
O6 N9 C4 118.1(2) . . ?
O6 N9 O5 125.0(2) . . ?
C7 O7 C6 110.48(18) 2_565 . ?
C8 O8 C11 109.13(19) . . ?
C10 O9 C9 110.95(19) . . ?

_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.968
_shelx_SHELXL_version_number     2014/7
_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.
;
