# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_201707-17
_database_code_depnum_ccdc_archive 'CCDC 1814221'
_audit_update_record             
;
2018-01-02 deposited with the CCDC.
2018-12-28 downloaded from the CCDC.
;
_audit_creation_date             2017-07-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H2 N6 O8'
_chemical_formula_sum            'C4 H2 N6 O8'
_chemical_formula_weight         262.12
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.542(2)
_cell_length_b                   8.4713(17)
_cell_length_c                   10.792(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.73(3)
_cell_angle_gamma                90
_cell_volume                     922.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2893
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4623
_cell_measurement_theta_min      2.0173
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.886
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6248
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.460
_diffrn_reflns_theta_min         3.139
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'multiwire proportional'
_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                1884
_reflns_number_total             2082
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2082
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0590
_refine_ls_restrained_S_all      1.173
_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)+(0.0449P)²+0.6652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1334
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
;
_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
O1 O 0.68794(18) 0.89836(19) 0.30368(17) 0.0334(4) Uani 1 1 d . . . A 1
O2 O 0.86970(16) 0.7649(2) 0.32938(18) 0.0341(4) Uani 1 1 d . . . A 1
O3 O 0.7507(2) 0.6769(2) 0.53654(17) 0.0393(5) Uani 1 1 d . . . . .
O4 O 0.63024(18) 0.4663(2) 0.47291(18) 0.0357(4) Uani 1 1 d . . . . .
O5 O 0.46558(18) 0.6967(2) 0.3174(2) 0.0410(5) Uani 1 1 d . . . . .
O6 O 0.49813(18) 0.6511(2) 0.13094(18) 0.0407(5) Uani 1 1 d . . . . .
O7 O 0.93267(18) 0.06282(19) 0.20334(18) 0.0320(4) Uani 1 1 d . . . B 1
O8 O 0.96113(18) 0.1331(2) 0.40425(17) 0.0367(4) Uani 1 1 d . . . B 1
N1 N 0.75211(19) 0.7770(2) 0.31458(18) 0.0234(4) Uani 1 1 d . . . A 1
N2 N 0.6879(2) 0.5840(2) 0.45525(19) 0.0271(4) Uani 1 1 d . . . . .
N3 N 0.53235(19) 0.6580(2) 0.2480(2) 0.0276(4) Uani 1 1 d . . . . .
N4 N 0.80481(17) 0.3782(2) 0.32904(17) 0.0200(4) Uani 1 1 d . . . . .
N5 N 0.84014(18) 0.2864(2) 0.24339(18) 0.0207(4) Uani 1 1 d . . . . .
N6 N 0.91881(19) 0.1475(2) 0.2889(2) 0.0255(4) Uani 1 1 d . . . B 1
C1 C 0.6782(2) 0.6194(3) 0.3139(2) 0.0217(5) Uani 1 1 d . . . . .
C2 C 0.7330(2) 0.4898(2) 0.2525(2) 0.0208(4) Uani 1 1 d . . . . .
C3 C 0.7247(2) 0.4684(3) 0.1210(2) 0.0252(5) Uani 1 1 d . . . . .
H3 H 0.6800 0.5331 0.0500 0.030 Uiso 1 1 calc R . . . .
C4 C 0.7955(2) 0.3334(3) 0.1181(2) 0.0242(5) Uani 1 1 d . . . . .
H4 H 0.8102 0.2836 0.0445 0.029 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
O1 N1 1.218(2) . ?
O2 N1 1.208(2) . ?
O3 N2 1.222(3) . ?
O4 N2 1.211(3) . ?
O5 N3 1.211(3) . ?
O6 N3 1.211(3) . ?
O7 N6 1.211(3) . ?
O8 N6 1.202(3) . ?
N1 C1 1.545(3) . ?
N2 C1 1.528(3) . ?
N3 C1 1.532(3) . ?
N4 N5 1.340(2) . ?
N4 C2 1.337(3) . ?
N5 N6 1.442(3) . ?
N5 C4 1.357(3) . ?
C1 C2 1.483(3) . ?
C2 C3 1.409(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.371(3) . ?
C4 H4 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
O1 N1 C1 117.63(18) . . ?
O2 N1 O1 127.23(19) . . ?
O2 N1 C1 115.11(17) . . ?
O3 N2 C1 117.18(19) . . ?
O4 N2 O3 127.6(2) . . ?
O4 N2 C1 115.22(19) . . ?
O5 N3 C1 117.0(2) . . ?
O6 N3 O5 127.3(2) . . ?
O6 N3 C1 115.60(19) . . ?
C2 N4 N5 101.81(17) . . ?
N4 N5 N6 119.04(17) . . ?
N4 N5 C4 115.59(18) . . ?
C4 N5 N6 125.36(18) . . ?
O7 N6 N5 114.06(19) . . ?
O8 N6 O7 129.8(2) . . ?
O8 N6 N5 116.18(18) . . ?
N2 C1 N1 106.04(17) . . ?
N2 C1 N3 105.99(17) . . ?
N3 C1 N1 104.78(16) . . ?
C2 C1 N1 112.41(18) . . ?
C2 C1 N2 112.19(17) . . ?
C2 C1 N3 114.72(18) . . ?
N4 C2 C1 118.14(19) . . ?
N4 C2 C3 113.01(19) . . ?
C3 C2 C1 128.8(2) . . ?
C2 C3 H3 127.6 . . ?
C4 C3 C2 104.7(2) . . ?
C4 C3 H3 127.6 . . ?
N5 C4 C3 104.86(19) . . ?
N5 C4 H4 127.6 . . ?
C3 C4 H4 127.6 . . ?

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
O1 N1 C1 N2 -90.7(2) . . . . ?
O1 N1 C1 N3 21.2(2) . . . . ?
O1 N1 C1 C2 146.4(2) . . . . ?
O2 N1 C1 N2 87.5(2) . . . . ?
O2 N1 C1 N3 -160.61(18) . . . . ?
O2 N1 C1 C2 -35.4(3) . . . . ?
O3 N2 C1 N1 -2.0(2) . . . . ?
O3 N2 C1 N3 -113.0(2) . . . . ?
O3 N2 C1 C2 121.1(2) . . . . ?
O4 N2 C1 N1 177.22(17) . . . . ?
O4 N2 C1 N3 66.2(2) . . . . ?
O4 N2 C1 C2 -59.7(2) . . . . ?
O5 N3 C1 N1 -91.9(2) . . . . ?
O5 N3 C1 N2 20.0(3) . . . . ?
O5 N3 C1 C2 144.3(2) . . . . ?
O6 N3 C1 N1 85.7(2) . . . . ?
O6 N3 C1 N2 -162.45(19) . . . . ?
O6 N3 C1 C2 -38.1(3) . . . . ?
N1 C1 C2 N4 106.6(2) . . . . ?
N1 C1 C2 C3 -70.7(3) . . . . ?
N2 C1 C2 N4 -12.8(3) . . . . ?
N2 C1 C2 C3 169.9(2) . . . . ?
N3 C1 C2 N4 -133.8(2) . . . . ?
N3 C1 C2 C3 48.9(3) . . . . ?
N4 N5 N6 O7 171.88(18) . . . . ?
N4 N5 N6 O8 -8.6(3) . . . . ?
N4 N5 C4 C3 0.2(3) . . . . ?
N4 C2 C3 C4 0.7(3) . . . . ?
N5 N4 C2 C1 -178.22(18) . . . . ?
N5 N4 C2 C3 -0.5(2) . . . . ?
N6 N5 C4 C3 179.20(19) . . . . ?
C1 C2 C3 C4 178.0(2) . . . . ?
C2 N4 N5 N6 -178.87(17) . . . . ?
C2 N4 N5 C4 0.2(2) . . . . ?
C2 C3 C4 N5 -0.5(2) . . . . ?
C4 N5 N6 O7 -7.1(3) . . . . ?
C4 N5 N6 O8 172.5(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_201709-6
_database_code_depnum_ccdc_archive 'CCDC 1878156'
_audit_update_record             
;
2018-11-09 deposited with the CCDC.
2018-12-28 downloaded from the CCDC.
;
_audit_creation_date             2017-09-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H2 N6 O8'
_chemical_formula_sum            'C4 H2 N6 O8'
_chemical_formula_weight         262.12
_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                   10.104(2)
_cell_length_b                   8.3288(17)
_cell_length_c                   12.031(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.80(3)
_cell_angle_gamma                90
_cell_volume                     946.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3147
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4662
_cell_measurement_theta_min      1.8108
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8266
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7356
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.513
_diffrn_reflns_theta_min         3.043
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'multiwire proportional'
_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                2030
_reflns_number_total             2160
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.186
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+0.5975P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1171
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Riding coordinates:
 N6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
O8 O 0.64562(13) 1.09934(16) 0.87335(11) 0.0232(3) Uani 1 1 d . . . A 2
O6 O 0.44390(16) 0.88402(16) 0.90791(12) 0.0282(3) Uani 1 1 d . . . B 1
O7 O 0.53227(15) 1.32635(16) 0.83188(12) 0.0268(3) Uani 1 1 d . . . A 2
O3 O 0.67877(16) 0.88727(19) 0.67823(14) 0.0353(4) Uani 1 1 d . . . . .
N1 N 0.49115(16) 0.77475(18) 0.86649(13) 0.0204(3) Uani 1 1 d . . . B 1
O5 O 0.52753(16) 0.64295(17) 0.90970(13) 0.0313(3) Uani 1 1 d . . . B 1
N3 N 0.43909(19) 0.6519(2) 0.67227(14) 0.0281(4) Uani 1 1 d . . . . .
N5 N 0.54705(15) 1.18364(18) 0.81155(13) 0.0182(3) Uani 1 1 d . . . A 2
N4 N 0.31389(17) 0.92824(19) 0.58149(13) 0.0226(3) Uani 1 1 d . . . . .
N2 N 0.65793(17) 0.8126(2) 0.75662(14) 0.0246(4) Uani 1 1 d . . . . .
N6 N 0.26790(16) 1.07837(19) 0.54718(13) 0.0227(3) Uani 1 1 d . . . . .
H6 H 0.2000 1.0964 0.4822 0.027 Uiso 1 1 d R . . . .
C3 C 0.44309(18) 1.1123(2) 0.71087(14) 0.0175(4) Uani 1 1 d . . . . .
C2 C 0.42174(17) 0.9479(2) 0.68271(14) 0.0173(3) Uani 1 1 d . . . . .
O1 O 0.32746(17) 0.60722(18) 0.67706(14) 0.0370(4) Uani 1 1 d . . . . .
O4 O 0.74413(16) 0.7433(2) 0.83811(14) 0.0402(4) Uani 1 1 d . . . . .
C1 C 0.50023(18) 0.8047(2) 0.74420(15) 0.0191(4) Uani 1 1 d . . . . .
C4 C 0.34112(18) 1.1930(2) 0.62105(16) 0.0205(4) Uani 1 1 d . . . . .
H4 H 0.3261 1.3057 0.6133 0.025 Uiso 1 1 calc R . . . .
O2 O 0.5058(2) 0.5926(2) 0.61645(15) 0.0466(5) 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
O8 N5 1.2295(19) . ?
O6 N1 1.214(2) . ?
O7 N5 1.233(2) . ?
O3 N2 1.209(2) . ?
N1 O5 1.214(2) . ?
N1 C1 1.527(2) . ?
N3 O1 1.208(2) . ?
N3 C1 1.540(2) . ?
N3 O2 1.212(2) . ?
N5 C3 1.421(2) . ?
N4 N6 1.347(2) . ?
N4 C2 1.325(2) . ?
N2 O4 1.202(2) . ?
N2 C1 1.548(2) . ?
N6 H6 0.8501 . ?
N6 C4 1.335(2) . ?
C3 C2 1.409(2) . ?
C3 C4 1.375(2) . ?
C2 C1 1.477(2) . ?
C4 H4 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
O6 N1 O5 127.25(16) . . ?
O6 N1 C1 116.11(14) . . ?
O5 N1 C1 116.59(15) . . ?
O1 N3 C1 115.00(16) . . ?
O1 N3 O2 127.81(18) . . ?
O2 N3 C1 117.18(17) . . ?
O8 N5 O7 124.03(15) . . ?
O8 N5 C3 118.11(15) . . ?
O7 N5 C3 117.85(14) . . ?
C2 N4 N6 104.42(14) . . ?
O3 N2 C1 113.89(15) . . ?
O4 N2 O3 127.34(18) . . ?
O4 N2 C1 118.74(16) . . ?
N4 N6 H6 121.6 . . ?
C4 N6 N4 114.26(14) . . ?
C4 N6 H6 124.1 . . ?
C2 C3 N5 127.97(15) . . ?
C4 C3 N5 125.85(16) . . ?
C4 C3 C2 106.18(15) . . ?
N4 C2 C3 110.28(15) . . ?
N4 C2 C1 118.75(16) . . ?
C3 C2 C1 130.93(15) . . ?
N1 C1 N3 104.90(14) . . ?
N1 C1 N2 109.03(13) . . ?
N3 C1 N2 106.45(14) . . ?
C2 C1 N1 114.16(14) . . ?
C2 C1 N3 110.43(14) . . ?
C2 C1 N2 111.42(15) . . ?
N6 C4 C3 104.86(15) . . ?
N6 C4 H4 127.6 . . ?
C3 C4 H4 127.6 . . ?

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
O8 N5 C3 C2 13.0(3) . . . . ?
O8 N5 C3 C4 -167.70(17) . . . . ?
O6 N1 C1 N3 -133.70(16) . . . . ?
O6 N1 C1 N2 112.62(17) . . . . ?
O6 N1 C1 C2 -12.7(2) . . . . ?
O7 N5 C3 C2 -166.63(18) . . . . ?
O7 N5 C3 C4 12.7(3) . . . . ?
O3 N2 C1 N1 -156.13(15) . . . . ?
O3 N2 C1 N3 91.21(18) . . . . ?
O3 N2 C1 C2 -29.2(2) . . . . ?
O5 N1 C1 N3 43.99(19) . . . . ?
O5 N1 C1 N2 -69.69(19) . . . . ?
O5 N1 C1 C2 165.00(15) . . . . ?
N5 C3 C2 N4 179.78(16) . . . . ?
N5 C3 C2 C1 -2.3(3) . . . . ?
N5 C3 C4 N6 -179.64(16) . . . . ?
N4 N6 C4 C3 0.0(2) . . . . ?
N4 C2 C1 N1 -116.55(17) . . . . ?
N4 C2 C1 N3 1.3(2) . . . . ?
N4 C2 C1 N2 119.41(17) . . . . ?
N6 N4 C2 C3 -0.3(2) . . . . ?
N6 N4 C2 C1 -178.60(15) . . . . ?
C3 C2 C1 N1 65.6(2) . . . . ?
C3 C2 C1 N3 -176.50(18) . . . . ?
C3 C2 C1 N2 -58.4(2) . . . . ?
C2 N4 N6 C4 0.2(2) . . . . ?
C2 C3 C4 N6 -0.2(2) . . . . ?
O1 N3 C1 N1 48.4(2) . . . . ?
O1 N3 C1 N2 163.90(15) . . . . ?
O1 N3 C1 C2 -75.0(2) . . . . ?
O4 N2 C1 N1 25.7(2) . . . . ?
O4 N2 C1 N3 -87.0(2) . . . . ?
O4 N2 C1 C2 152.60(17) . . . . ?
C4 C3 C2 N4 0.3(2) . . . . ?
C4 C3 C2 C1 178.32(18) . . . . ?
O2 N3 C1 N1 -132.91(17) . . . . ?
O2 N3 C1 N2 -17.4(2) . . . . ?
O2 N3 C1 C2 103.66(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
