# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_monomedabs
_database_code_depnum_ccdc_archive 'CCDC 1451182'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;
_audit_creation_date             2014-10-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 N8 O10'
_chemical_formula_sum            'C6 H4 N8 O10'
_chemical_formula_weight         348.17
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   7.6782(4)
_cell_length_b                   10.4292(6)
_cell_length_c                   8.3545(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.180(3)
_cell_angle_gamma                90
_cell_volume                     619.50(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7150
_cell_measurement_temperature    100
_cell_measurement_theta_max      74.584
_cell_measurement_theta_min      6.679
_shelx_estimated_absorpt_T_max   0.795
_shelx_estimated_absorpt_T_min   0.795
_exptl_absorpt_coefficient_mu    1.603
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1043 before and 0.0788 after correction.
The Ratio of minimum to maximum transmission is 0.8448.
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    1.867
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17130
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.720
_diffrn_reflns_theta_min         6.679
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1057
_reflns_number_total             1266
_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       ?
_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, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.100
_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)+(0.0343P)²+0.4910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0924
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O1 O 0.8369(2) 0.54793(14) 0.18561(18) 0.0266(3) Uani 1 1 d . . . . .
O2 O 0.6837(2) 0.45947(16) -0.06408(17) 0.0349(4) Uani 1 1 d . . . . .
O3 O 0.67119(18) 0.36660(13) 0.16383(15) 0.0200(3) Uani 1 1 d . . . . .
O4 O 0.93406(18) 0.71416(14) 0.79628(18) 0.0266(4) Uani 1 1 d . . . . .
O5 O 0.65255(19) 0.75814(14) 0.78519(17) 0.0246(3) Uani 1 1 d . . . . .
N1 N 0.7390(2) 0.46791(16) 0.0907(2) 0.0222(4) Uani 1 1 d . . . . .
N2 N 0.6726(2) 0.45352(15) 0.42989(18) 0.0155(3) Uani 1 1 d . . . . .
N3 N 0.7843(2) 0.54334(15) 0.53665(19) 0.0173(3) Uani 1 1 d . . . . .
N4 N 0.7633(2) 0.69762(15) 0.73983(19) 0.0185(4) Uani 1 1 d . . . . .
C1 C 0.7551(3) 0.36190(19) 0.3493(2) 0.0171(4) Uani 1 1 d . . . . .
H1A H 0.883(3) 0.3775(19) 0.388(3) 0.013(5) Uiso 1 1 d . . . . .
H1B H 0.728(3) 0.275(2) 0.374(3) 0.015(5) Uiso 1 1 d . . . . .
C2 C 0.4998(2) 0.45275(18) 0.4423(2) 0.0149(4) Uani 1 1 d . . . . .
C3 C 0.6826(2) 0.59929(18) 0.6131(2) 0.0164(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
O1 N1 1.200(2) . ?
O2 N1 1.202(2) . ?
O3 N1 1.414(2) . ?
O3 C1 1.437(2) . ?
O4 N4 1.226(2) . ?
O5 N4 1.228(2) . ?
N2 N3 1.353(2) . ?
N2 C1 1.446(2) . ?
N2 C2 1.369(2) . ?
N3 C3 1.317(2) . ?
N4 C3 1.436(2) . ?
C1 H1A 0.93(2) . ?
C1 H1B 0.96(2) . ?
C2 C2 1.378(4) 3_666 ?
C2 C3 1.408(2) 3_666 ?
C3 C2 1.407(2) 3_666 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O3 C1 113.77(14) . . ?
O1 N1 O2 129.81(18) . . ?
O1 N1 O3 118.36(15) . . ?
O2 N1 O3 111.83(16) . . ?
N3 N2 C1 118.96(14) . . ?
N3 N2 C2 110.21(14) . . ?
C2 N2 C1 129.72(15) . . ?
C3 N3 N2 106.36(15) . . ?
O4 N4 O5 124.98(16) . . ?
O4 N4 C3 119.03(15) . . ?
O5 N4 C3 115.97(15) . . ?
O3 C1 N2 112.51(15) . . ?
O3 C1 H1A 110.6(12) . . ?
O3 C1 H1B 102.4(12) . . ?
N2 C1 H1A 108.5(13) . . ?
N2 C1 H1B 110.8(12) . . ?
H1A C1 H1B 111.9(17) . . ?
N2 C2 C2 107.62(19) . 3_666 ?
N2 C2 C3 148.16(17) . 3_666 ?
C2 C2 C3 104.19(19) 3_666 3_666 ?
N3 C3 N4 120.27(16) . . ?
N3 C3 C2 111.60(16) . 3_666 ?
C2 C3 N4 128.10(16) 3_666 . ?

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
O4 N4 C3 N3 -11.8(3) . . . . ?
O4 N4 C3 C2 166.07(18) . . . 3_666 ?
O5 N4 C3 N3 169.26(16) . . . . ?
O5 N4 C3 C2 -12.9(3) . . . 3_666 ?
N1 O3 C1 N2 79.82(18) . . . . ?
N2 N3 C3 N4 178.09(15) . . . . ?
N2 N3 C3 C2 -0.1(2) . . . 3_666 ?
N3 N2 C1 O3 -121.00(17) . . . . ?
N3 N2 C2 C2 1.5(2) . . . 3_666 ?
N3 N2 C2 C3 178.8(3) . . . 3_666 ?
C1 O3 N1 O1 -9.6(2) . . . . ?
C1 O3 N1 O2 171.38(15) . . . . ?
C1 N2 N3 C3 -169.92(16) . . . . ?
C1 N2 C2 C2 169.02(19) . . . 3_666 ?
C1 N2 C2 C3 -13.6(4) . . . 3_666 ?
C2 N2 N3 C3 -0.84(19) . . . . ?
C2 N2 C1 O3 72.4(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_shrv295
_database_code_depnum_ccdc_archive 'CCDC 1451183'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 N8 O8'
_chemical_formula_sum            'C6 H4 N8 O8'
_chemical_formula_weight         316.17

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.523(7)
_cell_length_b                   5.429(4)
_cell_length_c                   10.246(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.233(10)
_cell_angle_gamma                90
_cell_volume                     564.8(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1186
_cell_measurement_theta_min      4.01
_cell_measurement_theta_max      24.92

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.859
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.128
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    0.173
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.5159
_exptl_absorpt_correction_T_max  0.7454

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4578
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.006
_diffrn_reflns_theta_max         26.254
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1135
_reflns_number_gt                790
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 v2014.11-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2014/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2008)'


_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)+(0.1021P)²+0.0278P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1135
_refine_ls_number_parameters     134
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1609
_refine_ls_wR_factor_gt          0.1229
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.357
_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 -0.0836(2) 0.8950(4) -0.1498(2) 0.0346(6) Uani 1 1 d . . . . .
O2 O 0.0382(2) 0.9712(4) -0.16875(19) 0.0419(6) Uani 1 1 d . . . . .
N3 N 0.1409(2) 0.8126(4) -0.1029(2) 0.0367(6) Uani 1 1 d . . . . .
C4 C 0.0836(2) 0.6493(4) -0.0467(2) 0.0246(6) Uani 1 1 d . . . . .
C5 C -0.0554(2) 0.6992(4) -0.0755(2) 0.0241(6) Uani 1 1 d . . . . .
N6 N 0.14167(19) 0.4483(4) 0.0293(2) 0.0270(6) Uani 1 1 d . . . . .
C7 C 0.2813(3) 0.3930(6) 0.0560(4) 0.0493(9) Uani 1 1 d D . . . .
H7A H 0.299(4) 0.221(5) 0.067(4) 0.059 Uiso 1 1 d D U . . .
H7B H 0.305(4) 0.456(7) -0.021(3) 0.059 Uiso 1 1 d D U . . .
N9 N 0.3777(2) 0.5825(5) 0.2667(2) 0.0415(7) Uani 1 1 d D . . . .
O8A O 0.3564(3) 0.6084(7) 0.1264(3) 0.0389(13) Uani 0.564(6) 1 d D . P A 1
O10A O 0.3391(4) 0.3669(7) 0.2950(6) 0.0422(12) Uani 0.564(6) 1 d D . P A 1
O11A O 0.4352(5) 0.7258(10) 0.3406(6) 0.0568(15) Uani 0.564(6) 1 d D . P A 1
O8B O 0.3389(4) 0.3690(8) 0.2117(5) 0.0285(12) Uani 0.436(6) 1 d D . P A 2
O10B O 0.4309(5) 0.6043(12) 0.3888(4) 0.0390(15) Uani 0.436(6) 1 d D . P A 2
O11B O 0.3557(4) 0.7805(7) 0.1919(4) 0.0344(14) Uani 0.436(6) 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
N1 C5 1.295(3) . ?
N1 O2 1.407(3) . ?
O2 N3 1.408(3) . ?
N3 C4 1.290(3) . ?
C4 N6 1.386(3) . ?
C4 C5 1.440(4) . ?
C5 N6 1.384(3) 3_565 ?
N6 C5 1.384(3) 3_565 ?
N6 C7 1.454(4) . ?
C7 O8A 1.487(5) . ?
C7 O8B 1.556(6) . ?
C7 H7A 0.95(3) . ?
C7 H7B 0.95(3) . ?
N9 O11A 1.142(4) . ?
N9 O10B 1.235(5) . ?
N9 O10A 1.297(4) . ?
N9 O11B 1.304(4) . ?
N9 O8B 1.307(5) . ?
N9 O8A 1.402(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 N1 O2 104.3(2) . . ?
N1 O2 N3 111.48(19) . . ?
C4 N3 O2 104.1(2) . . ?
N3 C4 N6 127.1(2) . . ?
N3 C4 C5 110.4(2) . . ?
N6 C4 C5 122.5(2) . . ?
N1 C5 N6 127.3(2) . 3_565 ?
N1 C5 C4 109.8(2) . . ?
N6 C5 C4 122.9(2) 3_565 . ?
C5 N6 C4 114.6(2) 3_565 . ?
C5 N6 C7 122.5(2) 3_565 . ?
C4 N6 C7 122.9(2) . . ?
N6 C7 O8A 108.1(3) . . ?
N6 C7 O8B 108.2(3) . . ?
N6 C7 H7A 112(2) . . ?
O8A C7 H7A 131(2) . . ?
O8B C7 H7A 77(2) . . ?
N6 C7 H7B 104(2) . . ?
O8A C7 H7B 84(2) . . ?
O8B C7 H7B 140(2) . . ?
H7A C7 H7B 112(3) . . ?
O11A N9 O10A 127.5(4) . . ?
O10B N9 O11B 118.6(4) . . ?
O10B N9 O8B 121.9(4) . . ?
O11B N9 O8B 119.4(3) . . ?
O11A N9 O8A 121.7(4) . . ?
O10A N9 O8A 110.2(4) . . ?
N9 O8A C7 109.9(3) . . ?
N9 O8B C7 111.1(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 O2 N3 0.1(3) . . . . ?
N1 O2 N3 C4 -0.2(3) . . . . ?
O2 N3 C4 N6 179.0(2) . . . . ?
O2 N3 C4 C5 0.2(3) . . . . ?
O2 N1 C5 N6 -179.3(2) . . . 3_565 ?
O2 N1 C5 C4 0.0(3) . . . . ?
N3 C4 C5 N1 -0.1(3) . . . . ?
N6 C4 C5 N1 -179.0(2) . . . . ?
N3 C4 C5 N6 179.2(2) . . . 3_565 ?
N6 C4 C5 N6 0.3(4) . . . 3_565 ?
N3 C4 N6 C5 -179.0(2) . . . 3_565 ?
C5 C4 N6 C5 -0.3(3) . . . 3_565 ?
N3 C4 N6 C7 -0.3(4) . . . . ?
C5 C4 N6 C7 178.4(2) . . . . ?
C5 N6 C7 O8A -122.8(3) 3_565 . . . ?
C4 N6 C7 O8A 58.6(4) . . . . ?
C5 N6 C7 O8B -55.5(3) 3_565 . . . ?
C4 N6 C7 O8B 125.9(3) . . . . ?
O11A N9 O8A C7 178.9(4) . . . . ?
O10A N9 O8A C7 7.1(4) . . . . ?
N6 C7 O8A N9 89.3(3) . . . . ?
O10B N9 O8B C7 -177.4(4) . . . . ?
O11B N9 O8B C7 5.1(5) . . . . ?
N6 C7 O8B N9 -88.1(4) . . . . ?

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.110


# start Validation Reply Form
_vrf_PLAT015_shrv295             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ...      Please Do ! 
RESPONSE: It is our policy to routinley not supply the HKL file unless 
specifically required.
;
# end Validation Reply Form

####################################################################### 
# 
# 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_shrv322
_database_code_depnum_ccdc_archive 'CCDC 1451184'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 N8 O8'
_chemical_formula_sum            'C7 H4 N8 O8'
_chemical_formula_weight         328.18

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.7227(14)
_cell_length_b                   11.8045(13)
_cell_length_c                   8.1445(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.200(4)
_cell_angle_gamma                90
_cell_volume                     1216.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2300
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      24.93

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.793
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.129
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.023
_exptl_absorpt_coefficient_mu    0.164
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.6716
_exptl_absorpt_correction_T_max  0.7454

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
__diffrn_radiation_source        'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11435
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.610
_diffrn_reflns_theta_max         26.515
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2509
_reflns_number_gt                1526
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 v2014.11-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2014/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_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)+(0.0661P)²+0.4867P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2509
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1411
_refine_ls_wR_factor_gt          0.1182
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
C1 C 0.29874(19) 0.5316(2) 0.7927(3) 0.0343(6) Uani 1 1 d . . . . .
N2 N 0.37397(16) 0.46113(18) 0.7721(3) 0.0400(5) Uani 1 1 d . . . . .
C3 C 0.3381(2) 0.3829(2) 0.6535(3) 0.0431(7) Uani 1 1 d . . . . .
N4 N 0.3944(2) 0.3014(2) 0.5988(3) 0.0623(7) Uani 1 1 d . . . . .
O5 O 0.3256(2) 0.2492(2) 0.4792(3) 0.0781(8) Uani 1 1 d . . . . .
N6 N 0.2264(2) 0.2992(2) 0.4604(3) 0.0721(8) Uani 1 1 d . . . . .
C7 C 0.2348(2) 0.3814(2) 0.5689(3) 0.0484(7) Uani 1 1 d . . . . .
N8 N 0.15633(19) 0.4580(2) 0.5941(3) 0.0493(6) Uani 1 1 d . . . . .
C9 C 0.19164(19) 0.5301(2) 0.7049(3) 0.0378(6) Uani 1 1 d . . . . .
N10 N 0.13915(16) 0.62042(19) 0.7624(3) 0.0409(5) Uani 1 1 d . . . . .
C11 C 0.0346(2) 0.6604(3) 0.7031(4) 0.0496(7) Uani 1 1 d . . . . .
H11A H 0.0071 0.6160 0.6078 0.060 Uiso 1 1 calc R U . . .
H11B H 0.0387 0.7387 0.6685 0.060 Uiso 1 1 calc R U . . .
O12 O -0.03670(17) 0.6518(2) 0.8293(3) 0.0723(7) Uani 1 1 d . . . . .
N13 N -0.0811(2) 0.5466(4) 0.8450(5) 0.0853(11) Uani 1 1 d . . . . .
O14 O -0.0480(3) 0.4699(3) 0.7621(5) 0.1117(11) Uani 1 1 d . . . . .
O15 O -0.1452(3) 0.5370(4) 0.9344(5) 0.1345(15) Uani 1 1 d . . . . .
C16 C 0.2061(2) 0.6813(2) 0.8790(3) 0.0400(6) Uani 1 1 d . . . . .
O17 O 0.18519(15) 0.76583(17) 0.9493(3) 0.0544(6) Uani 1 1 d . . . . .
N18 N 0.30261(16) 0.62316(18) 0.8968(3) 0.0365(5) Uani 1 1 d . . . . .
C19 C 0.3927(2) 0.6609(2) 1.0073(3) 0.0430(7) Uani 1 1 d . . . . .
H19A H 0.4528 0.6124 0.9941 0.052 Uiso 1 1 calc R U . . .
H19B H 0.4112 0.7375 0.9779 0.052 Uiso 1 1 calc R U . . .
O20 O 0.37155(15) 0.65878(15) 1.1757(2) 0.0481(5) Uani 1 1 d . . . . .
N21 N 0.3775(2) 0.5489(2) 1.2471(3) 0.0529(6) Uani 1 1 d . . . . .
O22 O 0.38750(17) 0.46964(18) 1.1600(3) 0.0617(6) Uani 1 1 d . . . . .
O23 O 0.3714(2) 0.5533(2) 1.3932(3) 0.0854(8) 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 1.293(3) . ?
C1 N18 1.371(3) . ?
C1 C9 1.469(4) . ?
N2 C3 1.378(3) . ?
C3 N4 1.306(4) . ?
C3 C7 1.417(4) . ?
N4 O5 1.382(4) . ?
O5 N6 1.387(4) . ?
N6 C7 1.309(4) . ?
C7 N8 1.379(4) . ?
N8 C9 1.285(3) . ?
C9 N10 1.367(3) . ?
N10 C16 1.403(3) . ?
N10 C11 1.445(3) . ?
C11 O12 1.445(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
O12 N13 1.376(4) . ?
N13 O15 1.156(4) . ?
N13 O14 1.231(4) . ?
C16 O17 1.194(3) . ?
C16 N18 1.400(3) . ?
N18 C19 1.449(3) . ?
C19 O20 1.426(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
O20 N21 1.420(3) . ?
N21 O22 1.189(3) . ?
N21 O23 1.202(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
N2 C1 N18 127.6(2) . . ?
N2 C1 C9 126.1(2) . . ?
N18 C1 C9 106.3(2) . . ?
C1 N2 C3 109.2(2) . . ?
N4 C3 N2 125.6(3) . . ?
N4 C3 C7 109.8(3) . . ?
N2 C3 C7 124.7(2) . . ?
C3 N4 O5 103.9(2) . . ?
N4 O5 N6 112.8(2) . . ?
C7 N6 O5 103.5(3) . . ?
N6 C7 N8 125.3(3) . . ?
N6 C7 C3 110.0(3) . . ?
N8 C7 C3 124.6(3) . . ?
C9 N8 C7 109.6(2) . . ?
N8 C9 N10 127.6(2) . . ?
N8 C9 C1 125.8(2) . . ?
N10 C9 C1 106.6(2) . . ?
C9 N10 C16 110.4(2) . . ?
C9 N10 C11 127.3(2) . . ?
C16 N10 C11 121.9(2) . . ?
N10 C11 O12 111.4(2) . . ?
N10 C11 H11A 109.3 . . ?
O12 C11 H11A 109.3 . . ?
N10 C11 H11B 109.3 . . ?
O12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
N13 O12 C11 115.1(3) . . ?
O15 N13 O14 125.4(4) . . ?
O15 N13 O12 118.1(5) . . ?
O14 N13 O12 116.4(3) . . ?
O17 C16 N18 126.7(3) . . ?
O17 C16 N10 127.0(2) . . ?
N18 C16 N10 106.3(2) . . ?
C1 N18 C16 110.5(2) . . ?
C1 N18 C19 126.8(2) . . ?
C16 N18 C19 122.6(2) . . ?
O20 C19 N18 111.9(2) . . ?
O20 C19 H19A 109.2 . . ?
N18 C19 H19A 109.2 . . ?
O20 C19 H19B 109.2 . . ?
N18 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
N21 O20 C19 113.8(2) . . ?
O22 N21 O23 130.3(3) . . ?
O22 N21 O20 118.6(2) . . ?
O23 N21 O20 111.1(2) . . ?

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
N18 C1 N2 C3 -178.7(2) . . . . ?
C9 C1 N2 C3 -0.1(3) . . . . ?
C1 N2 C3 N4 177.9(3) . . . . ?
C1 N2 C3 C7 0.0(4) . . . . ?
N2 C3 N4 O5 -178.0(2) . . . . ?
C7 C3 N4 O5 0.1(3) . . . . ?
C3 N4 O5 N6 0.1(3) . . . . ?
N4 O5 N6 C7 -0.3(4) . . . . ?
O5 N6 C7 N8 178.3(3) . . . . ?
O5 N6 C7 C3 0.3(3) . . . . ?
N4 C3 C7 N6 -0.3(4) . . . . ?
N2 C3 C7 N6 177.9(3) . . . . ?
N4 C3 C7 N8 -178.3(3) . . . . ?
N2 C3 C7 N8 -0.1(4) . . . . ?
N6 C7 N8 C9 -177.5(3) . . . . ?
C3 C7 N8 C9 0.2(4) . . . . ?
C7 N8 C9 N10 178.7(2) . . . . ?
C7 N8 C9 C1 -0.2(4) . . . . ?
N2 C1 C9 N8 0.2(4) . . . . ?
N18 C1 C9 N8 179.1(2) . . . . ?
N2 C1 C9 N10 -178.9(2) . . . . ?
N18 C1 C9 N10 0.0(3) . . . . ?
N8 C9 N10 C16 -177.9(2) . . . . ?
C1 C9 N10 C16 1.2(3) . . . . ?
N8 C9 N10 C11 -5.0(4) . . . . ?
C1 C9 N10 C11 174.1(2) . . . . ?
C9 N10 C11 O12 116.9(3) . . . . ?
C16 N10 C11 O12 -71.0(3) . . . . ?
N10 C11 O12 N13 -82.6(3) . . . . ?
C11 O12 N13 O15 -173.8(3) . . . . ?
C11 O12 N13 O14 6.6(4) . . . . ?
C9 N10 C16 O17 178.1(3) . . . . ?
C11 N10 C16 O17 4.8(4) . . . . ?
C9 N10 C16 N18 -1.9(3) . . . . ?
C11 N10 C16 N18 -175.2(2) . . . . ?
N2 C1 N18 C16 177.7(2) . . . . ?
C9 C1 N18 C16 -1.2(3) . . . . ?
N2 C1 N18 C19 -0.1(4) . . . . ?
C9 C1 N18 C19 -178.9(2) . . . . ?
O17 C16 N18 C1 -178.1(3) . . . . ?
N10 C16 N18 C1 1.9(3) . . . . ?
O17 C16 N18 C19 -0.3(4) . . . . ?
N10 C16 N18 C19 179.8(2) . . . . ?
C1 N18 C19 O20 -118.9(3) . . . . ?
C16 N18 C19 O20 63.6(3) . . . . ?
N18 C19 O20 N21 78.2(3) . . . . ?
C19 O20 N21 O22 -7.9(3) . . . . ?
C19 O20 N21 O23 171.9(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
C19 H19B O23 0.97 2.60 3.502(4) 154.9 4_575

_refine_diff_density_max         0.535
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.046


# start Validation Reply Form
_vrf_PLAT015_shrv322             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.

;
# end Validation Reply Form
####################################################################### 
# 
# 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_shrv306
_database_code_depnum_ccdc_archive 'CCDC 1451185'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 N10 O10'
_chemical_formula_sum            'C6 H4 N10 O10'
_chemical_formula_weight         376.19

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'

_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, -y, -z'

_cell_length_a                   6.4891(3)
_cell_length_b                   8.1203(4)
_cell_length_c                   13.7172(7)
_cell_angle_alpha                98.6470(10)
_cell_angle_beta                 92.0850(10)
_cell_angle_gamma                109.154(2)
_cell_volume                     672.18(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3188
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      26.34

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.859
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.336
_exptl_crystal_size_min          0.061
_exptl_absorpt_coefficient_mu    0.176
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.6989
_exptl_absorpt_correction_T_max  0.7454

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6438
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0132
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.508
_diffrn_reflns_theta_max         26.441
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2732
_reflns_number_gt                2270
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 v2014.11-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2014/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_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)+(0.0420P)²+0.2312P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2732
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0940
_refine_ls_wR_factor_gt          0.0862
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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
N1A N -0.0674(2) 0.17712(16) 0.07767(9) 0.0313(3) Uani 1 1 d . . . . .
C2A C 0.0302(2) 0.09593(19) 0.01363(11) 0.0282(3) Uani 1 1 d . . . . .
N3A N 0.1998(2) 0.21665(16) -0.02012(9) 0.0285(3) Uani 1 1 d . . . . .
N4A N 0.2171(2) 0.38154(16) 0.02481(9) 0.0307(3) Uani 1 1 d . . . . .
C5A C 0.0542(2) 0.34618(19) 0.08077(11) 0.0292(3) Uani 1 1 d . . . . .
N6A N 0.0133(2) 0.48776(17) 0.14687(10) 0.0353(3) Uani 1 1 d . . . . .
O7A O 0.1235(2) 0.63999(15) 0.14180(9) 0.0443(3) Uani 1 1 d . . . . .
O8A O -0.1243(3) 0.44517(18) 0.20417(11) 0.0596(4) Uani 1 1 d . . . . .
C9A C 0.3617(3) 0.1968(2) -0.08830(12) 0.0342(3) Uani 1 1 d . . . . .
H9A1 H 0.5074 0.2517 -0.0541 0.041 Uiso 1 1 calc R U . . .
H9A2 H 0.3383 0.0720 -0.1091 0.041 Uiso 1 1 calc R U . . .
O10A O 0.34883(19) 0.27483(15) -0.17300(8) 0.0395(3) Uani 1 1 d . . . . .
N11A N 0.1760(2) 0.1682(2) -0.24664(10) 0.0400(3) Uani 1 1 d . . . . .
O12A O 0.0395(2) 0.04478(17) -0.22359(10) 0.0504(3) Uani 1 1 d . . . . .
O13A O 0.1930(3) 0.2233(2) -0.32310(10) 0.0585(4) Uani 1 1 d . . . . .
N1B N 0.5168(2) 0.31474(18) 0.40927(9) 0.0338(3) Uani 1 1 d . . . . .
C2B C 0.4771(2) 0.4591(2) 0.44803(11) 0.0307(3) Uani 1 1 d . . . . .
N3B N 0.3840(2) 0.52066(17) 0.37803(9) 0.0326(3) Uani 1 1 d . . . . .
N4B N 0.3584(2) 0.41165(18) 0.28970(9) 0.0351(3) Uani 1 1 d . . . . .
C5B C 0.4413(3) 0.2948(2) 0.31450(11) 0.0319(3) Uani 1 1 d . . . . .
N6B N 0.4553(2) 0.14985(19) 0.24122(10) 0.0381(3) Uani 1 1 d . . . . .
O7B O 0.4019(2) 0.14698(19) 0.15499(9) 0.0512(3) Uani 1 1 d . . . . .
O8B O 0.5223(3) 0.0423(2) 0.27167(10) 0.0623(4) Uani 1 1 d . . . . .
C9B C 0.3268(3) 0.6802(2) 0.38375(12) 0.0386(4) Uani 1 1 d . . . . .
H9B1 H 0.4439 0.7810 0.4205 0.046 Uiso 1 1 calc R U . . .
H9B2 H 0.3018 0.7038 0.3179 0.046 Uiso 1 1 calc R U . . .
O10B O 0.1310(2) 0.64885(16) 0.43357(10) 0.0465(3) Uani 1 1 d . . . . .
N11B N 0.1248(3) 0.8020(2) 0.49703(13) 0.0500(4) Uani 1 1 d . . . . .
O12B O 0.2540(3) 0.94105(18) 0.48910(13) 0.0663(4) Uani 1 1 d . . . . .
O13B O -0.0184(3) 0.7686(2) 0.54982(15) 0.0848(6) 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
N1A C2A 1.3222(19) . ?
N1A C5A 1.3334(19) . ?
C2A N3A 1.3608(19) . ?
C2A C2A 1.461(3) 2 ?
N3A N4A 1.3542(17) . ?
N3A C9A 1.4635(19) . ?
N4A C5A 1.310(2) . ?
C5A N6A 1.4556(18) . ?
N6A O8A 1.2100(19) . ?
N6A O7A 1.2222(18) . ?
C9A O10A 1.4168(19) . ?
C9A H9A1 0.9700 . ?
C9A H9A2 0.9700 . ?
O10A N11A 1.4301(19) . ?
N11A O12A 1.1925(19) . ?
N11A O13A 1.1958(19) . ?
N1B C2B 1.320(2) . ?
N1B C5B 1.340(2) . ?
C2B N3B 1.356(2) . ?
C2B C2B 1.455(3) 2_666 ?
N3B N4B 1.3584(17) . ?
N3B C9B 1.452(2) . ?
N4B C5B 1.313(2) . ?
C5B N6B 1.458(2) . ?
N6B O8B 1.2130(19) . ?
N6B O7B 1.2150(18) . ?
C9B O10B 1.432(2) . ?
C9B H9B1 0.9700 . ?
C9B H9B2 0.9700 . ?
O10B N11B 1.420(2) . ?
N11B O13B 1.185(2) . ?
N11B O12B 1.188(2) . ?

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
C2A N1A C5A 101.38(12) . . ?
N1A C2A N3A 110.20(13) . . ?
N1A C2A C2A 124.69(17) . 2 ?
N3A C2A C2A 125.08(17) . 2 ?
N4A N3A C2A 109.35(12) . . ?
N4A N3A C9A 118.53(12) . . ?
C2A N3A C9A 132.03(13) . . ?
C5A N4A N3A 100.98(12) . . ?
N4A C5A N1A 118.07(13) . . ?
N4A C5A N6A 120.56(13) . . ?
N1A C5A N6A 121.33(13) . . ?
O8A N6A O7A 125.07(14) . . ?
O8A N6A C5A 117.27(13) . . ?
O7A N6A C5A 117.64(14) . . ?
O10A C9A N3A 111.99(12) . . ?
O10A C9A H9A1 109.2 . . ?
N3A C9A H9A1 109.2 . . ?
O10A C9A H9A2 109.2 . . ?
N3A C9A H9A2 109.2 . . ?
H9A1 C9A H9A2 107.9 . . ?
C9A O10A N11A 113.95(12) . . ?
O12A N11A O13A 130.50(17) . . ?
O12A N11A O10A 117.63(13) . . ?
O13A N11A O10A 111.85(15) . . ?
C2B N1B C5B 101.09(12) . . ?
N1B C2B N3B 110.87(13) . . ?
N1B C2B C2B 125.13(17) . 2_666 ?
N3B C2B C2B 123.99(17) . 2_666 ?
C2B N3B N4B 109.14(12) . . ?
C2B N3B C9B 130.71(13) . . ?
N4B N3B C9B 120.01(13) . . ?
C5B N4B N3B 101.02(12) . . ?
N4B C5B N1B 117.87(14) . . ?
N4B C5B N6B 121.33(14) . . ?
N1B C5B N6B 120.79(14) . . ?
O8B N6B O7B 125.23(15) . . ?
O8B N6B C5B 116.82(14) . . ?
O7B N6B C5B 117.94(14) . . ?
O10B C9B N3B 106.40(13) . . ?
O10B C9B H9B1 110.4 . . ?
N3B C9B H9B1 110.4 . . ?
O10B C9B H9B2 110.4 . . ?
N3B C9B H9B2 110.4 . . ?
H9B1 C9B H9B2 108.6 . . ?
N11B O10B C9B 112.90(13) . . ?
O13B N11B O12B 129.63(18) . . ?
O13B N11B O10B 112.23(16) . . ?
O12B N11B O10B 118.11(16) . . ?

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
C5A N1A C2A N3A -1.27(16) . . . . ?
C5A N1A C2A C2A 176.41(18) . . . 2 ?
N1A C2A N3A N4A 1.45(16) . . . . ?
C2A C2A N3A N4A -176.22(17) 2 . . . ?
N1A C2A N3A C9A 177.84(14) . . . . ?
C2A C2A N3A C9A 0.2(3) 2 . . . ?
C2A N3A N4A C5A -0.90(15) . . . . ?
C9A N3A N4A C5A -177.84(12) . . . . ?
N3A N4A C5A N1A 0.09(17) . . . . ?
N3A N4A C5A N6A 177.89(12) . . . . ?
C2A N1A C5A N4A 0.75(18) . . . . ?
C2A N1A C5A N6A -177.03(13) . . . . ?
N4A C5A N6A O8A -172.24(15) . . . . ?
N1A C5A N6A O8A 5.5(2) . . . . ?
N4A C5A N6A O7A 6.2(2) . . . . ?
N1A C5A N6A O7A -176.10(14) . . . . ?
N4A N3A C9A O10A -64.98(17) . . . . ?
C2A N3A C9A O10A 118.91(17) . . . . ?
N3A C9A O10A N11A -79.64(15) . . . . ?
C9A O10A N11A O12A 13.33(19) . . . . ?
C9A O10A N11A O13A -168.05(13) . . . . ?
C5B N1B C2B N3B -0.50(17) . . . . ?
C5B N1B C2B C2B 178.59(19) . . . 2_666 ?
N1B C2B N3B N4B 0.82(18) . . . . ?
C2B C2B N3B N4B -178.28(18) 2_666 . . . ?
N1B C2B N3B C9B -174.93(16) . . . . ?
C2B C2B N3B C9B 6.0(3) 2_666 . . . ?
C2B N3B N4B C5B -0.72(16) . . . . ?
C9B N3B N4B C5B 175.56(14) . . . . ?
N3B N4B C5B N1B 0.45(18) . . . . ?
N3B N4B C5B N6B -178.33(14) . . . . ?
C2B N1B C5B N4B 0.02(19) . . . . ?
C2B N1B C5B N6B 178.81(14) . . . . ?
N4B C5B N6B O8B -175.82(16) . . . . ?
N1B C5B N6B O8B 5.4(2) . . . . ?
N4B C5B N6B O7B 5.0(2) . . . . ?
N1B C5B N6B O7B -173.73(15) . . . . ?
C2B N3B C9B O10B -76.4(2) . . . . ?
N4B N3B C9B O10B 108.28(15) . . . . ?
N3B C9B O10B N11B 143.45(13) . . . . ?
C9B O10B N11B O13B -168.29(17) . . . . ?
C9B O10B N11B O12B 13.5(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
C9A H9A2 N1A 0.97 2.31 3.039(2) 131.0 2
C9A H9A2 O8B 0.97 2.59 3.208(2) 121.4 2_655
C9B H9B1 O12B 0.97 2.56 3.529(2) 176.5 2_676
C9B H9B2 O7A 0.97 2.54 3.455(2) 156.5 .

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.040

# start Validation Reply Form
_vrf_PLAT015_shrv306             
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PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinley not supply the HKL file unless 
specifically required.

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# end Validation Reply Form
