# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_shrv585
_database_code_depnum_ccdc_archive 'CCDC 1811781'
_audit_update_record             
;
2017-12-16 deposited with the CCDC.
2018-03-01 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 H N11 O14'
_chemical_formula_sum            'C7 H N11 O14'
_chemical_formula_weight         463.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   17.130(3)
_cell_length_b                   6.8390(11)
_cell_length_c                   27.832(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.850(6)
_cell_angle_gamma                90
_cell_volume                     3253.1(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8152
_cell_measurement_theta_min      3.183
_cell_measurement_theta_max      74.759

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.891
_exptl_crystal_F_000             1856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.670
_shelx_estimated_absorpt_T_min   0.683
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6057
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   '1uS microfocus'
_diffrn_radiation_monochromator  'HELIOS multilayer optics'
_diffrn_measurement_device_type  'Photon 100'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8864
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.183
_diffrn_reflns_theta_max         68.233
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.948
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.948
_reflns_number_total             2818
_reflns_number_gt                2565
_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 APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_special_details          
;
One nitro group (N14, O15, O16) displays 2-component disorder with a 
56:44 ratio between major and minor components.  Enhanced rigid bond
restraints (esds = 0.001) have been applied to disordered atoms.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0586P)²+5.2724P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0070(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2818
_refine_ls_number_parameters     309
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1321
_refine_ls_wR_factor_gt          0.1283
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.046
_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
O1 O 0.73280(13) 0.7795(5) 0.42660(10) 0.0954(8) Uani 1 1 d . . . . .
O2 O 0.63179(14) 0.9239(3) 0.39227(8) 0.0723(6) Uani 1 1 d . . . . .
N3 N 0.66394(13) 0.8047(4) 0.41810(8) 0.0554(6) Uani 1 1 d . . . . .
C4 C 0.60742(13) 0.6695(3) 0.44448(8) 0.0436(6) Uani 1 1 d . . . . .
N5 N 0.64836(13) 0.4717(3) 0.45805(7) 0.0529(6) Uani 1 1 d . . . . .
O6 O 0.70206(18) 0.4901(4) 0.48735(11) 0.1148(11) Uani 1 1 d . . . . .
O7 O 0.62239(13) 0.3316(3) 0.43906(7) 0.0656(6) Uani 1 1 d . . . . .
N8 N 0.59224(14) 0.7696(4) 0.49272(8) 0.0576(6) Uani 1 1 d . . . . .
O9 O 0.61062(16) 0.9381(4) 0.49638(9) 0.0851(7) Uani 1 1 d . . . . .
O10 O 0.56330(15) 0.6657(4) 0.52136(8) 0.0816(7) Uani 1 1 d . . . . .
N11 N 0.53547(10) 0.6468(3) 0.41689(7) 0.0398(5) Uani 1 1 d . . . . .
N12 N 0.47245(12) 0.7471(3) 0.43242(7) 0.0467(5) Uani 1 1 d . . . . .
C13 C 0.41843(13) 0.7203(4) 0.39815(9) 0.0445(6) Uani 1 1 d . . . . .
N14 N 0.34057(13) 0.8042(4) 0.40285(10) 0.0608(6) Uani 1 1 d D . . . .
O15A O 0.3192(4) 0.9160(18) 0.3721(4) 0.107(3) Uani 0.556(17) 1 d D . P A 1
O16A O 0.3095(5) 0.7595(15) 0.4387(3) 0.106(3) Uani 0.556(17) 1 d D . P A 1
O15B O 0.2868(4) 0.6896(11) 0.4032(7) 0.124(6) Uani 0.444(17) 1 d D . P A 2
O16B O 0.3311(6) 0.9747(9) 0.4009(7) 0.102(4) Uani 0.444(17) 1 d D . P A 2
C17 C 0.44375(13) 0.6085(4) 0.36037(8) 0.0431(5) Uani 1 1 d . . . . .
N18 N 0.39996(14) 0.5601(4) 0.31622(9) 0.0649(7) Uani 1 1 d . . . . .
O19 O 0.43125(13) 0.4791(5) 0.28541(8) 0.0907(9) Uani 1 1 d . . . . .
O20 O 0.33234(17) 0.6049(8) 0.31338(13) 0.168(2) Uani 1 1 d . . . . .
C21 C 0.52049(13) 0.5621(3) 0.37261(8) 0.0372(5) Uani 1 1 d . . . . .
C22 C 0.57719(12) 0.4553(3) 0.34544(7) 0.0357(5) Uani 1 1 d . . . . .
C23 C 0.57188(13) 0.2668(3) 0.32549(8) 0.0389(5) Uani 1 1 d . . . . .
N24 N 0.50967(15) 0.1294(3) 0.33091(9) 0.0598(6) Uani 1 1 d . . . . .
O25 O 0.47024(15) 0.1546(4) 0.36492(11) 0.0927(9) Uani 1 1 d . . . . .
O26 O 0.50162(19) -0.0038(4) 0.30325(11) 0.1134(11) Uani 1 1 d . . . . .
C27 C 0.63805(13) 0.2488(3) 0.30065(8) 0.0399(5) Uani 1 1 d . . . . .
N28 N 0.66729(13) 0.0945(3) 0.27112(8) 0.0510(5) Uani 1 1 d . . . . .
O29 O 0.70423(12) 0.1451(3) 0.23799(7) 0.0670(6) Uani 1 1 d . . . . .
O30 O 0.6526(2) -0.0711(3) 0.28061(11) 0.1137(11) Uani 1 1 d . . . . .
N31 N 0.67833(11) 0.4143(3) 0.30689(7) 0.0420(5) Uani 1 1 d . . . . .
H31 H 0.7224 0.4360 0.2947 0.050 Uiso 1 1 calc R U . . .
N32 N 0.64260(11) 0.5431(3) 0.33422(7) 0.0414(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
O1 N3 1.200(3) . ?
O2 N3 1.196(3) . ?
N3 C4 1.558(3) . ?
C4 N11 1.416(3) . ?
C4 N8 1.545(3) . ?
C4 N5 1.558(3) . ?
N5 O7 1.167(3) . ?
N5 O6 1.194(3) . ?
N8 O9 1.197(3) . ?
N8 O10 1.200(3) . ?
N11 C21 1.370(3) . ?
N11 N12 1.373(3) . ?
N12 C13 1.296(3) . ?
C13 C17 1.393(3) . ?
C13 N14 1.466(3) . ?
N14 O16B 1.178(6) . ?
N14 O15A 1.187(6) . ?
N14 O16A 1.202(5) . ?
N14 O15B 1.210(6) . ?
C17 C21 1.373(3) . ?
C17 N18 1.435(3) . ?
N18 O19 1.180(3) . ?
N18 O20 1.196(3) . ?
C21 C22 1.465(3) . ?
C22 N32 1.327(3) . ?
C22 C23 1.404(3) . ?
C23 C27 1.372(3) . ?
C23 N24 1.436(3) . ?
N24 O26 1.194(3) . ?
N24 O25 1.212(3) . ?
C27 N31 1.331(3) . ?
C27 N28 1.448(3) . ?
N28 O30 1.194(3) . ?
N28 O29 1.203(3) . ?
N31 N32 1.339(3) . ?
N31 H31 0.8600 . ?

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
O2 N3 O1 128.6(3) . . ?
O2 N3 C4 114.3(2) . . ?
O1 N3 C4 117.1(3) . . ?
N11 C4 N8 109.19(18) . . ?
N11 C4 N3 110.80(19) . . ?
N8 C4 N3 107.00(19) . . ?
N11 C4 N5 113.42(19) . . ?
N8 C4 N5 105.88(19) . . ?
N3 C4 N5 110.23(19) . . ?
O7 N5 O6 130.4(3) . . ?
O7 N5 C4 116.79(19) . . ?
O6 N5 C4 112.8(2) . . ?
O9 N8 O10 129.2(3) . . ?
O9 N8 C4 116.3(3) . . ?
O10 N8 C4 114.6(2) . . ?
C21 N11 N12 113.00(18) . . ?
C21 N11 C4 129.61(18) . . ?
N12 N11 C4 116.65(18) . . ?
C13 N12 N11 103.60(18) . . ?
N12 C13 C17 112.9(2) . . ?
N12 C13 N14 119.2(2) . . ?
C17 C13 N14 127.8(2) . . ?
O15A N14 O16A 129.1(6) . . ?
O16B N14 O15B 122.6(6) . . ?
O16B N14 C13 120.5(5) . . ?
O15A N14 C13 115.2(5) . . ?
O16A N14 C13 115.5(4) . . ?
O15B N14 C13 116.4(4) . . ?
C21 C17 C13 106.3(2) . . ?
C21 C17 N18 126.6(2) . . ?
C13 C17 N18 127.0(2) . . ?
O19 N18 O20 123.9(3) . . ?
O19 N18 C17 119.6(2) . . ?
O20 N18 C17 116.5(3) . . ?
N11 C21 C17 104.11(19) . . ?
N11 C21 C22 125.75(19) . . ?
C17 C21 C22 130.1(2) . . ?
N32 C22 C23 110.85(19) . . ?
N32 C22 C21 119.68(19) . . ?
C23 C22 C21 129.3(2) . . ?
C27 C23 C22 104.33(19) . . ?
C27 C23 N24 129.6(2) . . ?
C22 C23 N24 126.0(2) . . ?
O26 N24 O25 124.5(3) . . ?
O26 N24 C23 119.1(2) . . ?
O25 N24 C23 116.4(2) . . ?
N31 C27 C23 107.27(19) . . ?
N31 C27 N28 119.9(2) . . ?
C23 C27 N28 132.9(2) . . ?
O30 N28 O29 124.9(2) . . ?
O30 N28 C27 118.7(2) . . ?
O29 N28 C27 116.5(2) . . ?
C27 N31 N32 112.39(18) . . ?
C27 N31 H31 123.8 . . ?
N32 N31 H31 123.8 . . ?
C22 N32 N31 105.14(18) . . ?

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
O2 N3 C4 N11 28.8(3) . . . . ?
O1 N3 C4 N11 -152.4(2) . . . . ?
O2 N3 C4 N8 -90.1(2) . . . . ?
O1 N3 C4 N8 88.7(3) . . . . ?
O2 N3 C4 N5 155.2(2) . . . . ?
O1 N3 C4 N5 -26.0(3) . . . . ?
N11 C4 N5 O7 10.4(3) . . . . ?
N8 C4 N5 O7 130.1(2) . . . . ?
N3 C4 N5 O7 -114.5(3) . . . . ?
N11 C4 N5 O6 -168.9(3) . . . . ?
N8 C4 N5 O6 -49.2(3) . . . . ?
N3 C4 N5 O6 66.2(3) . . . . ?
N11 C4 N8 O9 -105.1(3) . . . . ?
N3 C4 N8 O9 14.9(3) . . . . ?
N5 C4 N8 O9 132.5(3) . . . . ?
N11 C4 N8 O10 74.8(3) . . . . ?
N3 C4 N8 O10 -165.2(2) . . . . ?
N5 C4 N8 O10 -47.6(3) . . . . ?
N8 C4 N11 C21 -178.3(2) . . . . ?
N3 C4 N11 C21 64.1(3) . . . . ?
N5 C4 N11 C21 -60.5(3) . . . . ?
N8 C4 N11 N12 12.4(3) . . . . ?
N3 C4 N11 N12 -105.2(2) . . . . ?
N5 C4 N11 N12 130.2(2) . . . . ?
C21 N11 N12 C13 1.3(3) . . . . ?
C4 N11 N12 C13 172.4(2) . . . . ?
N11 N12 C13 C17 -0.8(3) . . . . ?
N11 N12 C13 N14 178.5(2) . . . . ?
N12 C13 N14 O16B 69.4(12) . . . . ?
C17 C13 N14 O16B -111.3(11) . . . . ?
N12 C13 N14 O15A 120.6(8) . . . . ?
C17 C13 N14 O15A -60.2(9) . . . . ?
N12 C13 N14 O16A -55.0(8) . . . . ?
C17 C13 N14 O16A 124.3(7) . . . . ?
N12 C13 N14 O15B -118.7(11) . . . . ?
C17 C13 N14 O15B 60.6(11) . . . . ?
N12 C13 C17 C21 0.1(3) . . . . ?
N14 C13 C17 C21 -179.2(2) . . . . ?
N12 C13 C17 N18 -176.8(3) . . . . ?
N14 C13 C17 N18 3.9(4) . . . . ?
C21 C17 N18 O19 -3.2(5) . . . . ?
C13 C17 N18 O19 173.0(3) . . . . ?
C21 C17 N18 O20 176.2(4) . . . . ?
C13 C17 N18 O20 -7.6(5) . . . . ?
N12 N11 C21 C17 -1.3(3) . . . . ?
C4 N11 C21 C17 -170.9(2) . . . . ?
N12 N11 C21 C22 176.3(2) . . . . ?
C4 N11 C21 C22 6.7(4) . . . . ?
C13 C17 C21 N11 0.7(3) . . . . ?
N18 C17 C21 N11 177.6(2) . . . . ?
C13 C17 C21 C22 -176.8(2) . . . . ?
N18 C17 C21 C22 0.1(4) . . . . ?
N11 C21 C22 N32 -57.5(3) . . . . ?
C17 C21 C22 N32 119.5(3) . . . . ?
N11 C21 C22 C23 126.9(3) . . . . ?
C17 C21 C22 C23 -56.1(4) . . . . ?
N32 C22 C23 C27 -1.1(2) . . . . ?
C21 C22 C23 C27 174.8(2) . . . . ?
N32 C22 C23 N24 179.0(2) . . . . ?
C21 C22 C23 N24 -5.1(4) . . . . ?
C27 C23 N24 O26 -18.3(4) . . . . ?
C22 C23 N24 O26 161.6(3) . . . . ?
C27 C23 N24 O25 159.3(3) . . . . ?
C22 C23 N24 O25 -20.8(4) . . . . ?
C22 C23 C27 N31 1.0(2) . . . . ?
N24 C23 C27 N31 -179.2(2) . . . . ?
C22 C23 C27 N28 -178.0(2) . . . . ?
N24 C23 C27 N28 1.8(4) . . . . ?
N31 C27 N28 O30 149.3(3) . . . . ?
C23 C27 N28 O30 -31.8(4) . . . . ?
N31 C27 N28 O29 -31.7(3) . . . . ?
C23 C27 N28 O29 147.2(3) . . . . ?
C23 C27 N31 N32 -0.5(3) . . . . ?
N28 C27 N31 N32 178.65(19) . . . . ?
C23 C22 N32 N31 0.8(2) . . . . ?
C21 C22 N32 N31 -175.56(19) . . . . ?
C27 N31 N32 C22 -0.2(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
N31 H31 O29 0.86 2.15 2.905(3) 146.7 4_655

_refine_diff_density_max         0.318
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.058

# start Validation Reply Form
_vrf_PLAT015_shrv585             
;
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

# start Validation Reply Form
_vrf_PLAT029_shrv585             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.948 Note  
RESPONSE: Low data completeness is often encountered in low symmetry unit 
cells when utilizing Cu radiation.
;
_vrf_PLAT430_shrv585             
;
PROBLEM: Short Inter D...A Contact  O1     ..  O16B    ..       2.80 Ang.  
RESPONSE: High-density energetic materials often display close contacts.
;
####################################################################### 
# 
# 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_shrv587
_database_code_depnum_ccdc_archive 'CCDC 1811782'
_audit_update_record             
;
2017-12-16 deposited with the CCDC.
2018-03-01 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 H N8 O8, K, H2 O'
_chemical_formula_sum            'C6 H3 K N8 O9'
_chemical_formula_weight         370.26

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'
K K 0.2009 0.2494 '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                   7.3543(3)
_cell_length_b                   9.0468(3)
_cell_length_c                   10.7236(4)
_cell_angle_alpha                105.6180(10)
_cell_angle_beta                 94.5290(10)
_cell_angle_gamma                108.8990(10)
_cell_volume                     639.18(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3692
_cell_measurement_theta_min      2.676
_cell_measurement_theta_max      29.461

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.924
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.491
_shelx_estimated_absorpt_T_min   0.895
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6963
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            9186
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.273
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3519
_reflns_number_gt                2813
_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 APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_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)+(0.0376P)²+0.2010P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3519
_refine_ls_number_parameters     223
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0885
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.004
_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
O1 O 1.28484(18) 0.46988(17) 1.00694(12) 0.0510(3) Uani 1 1 d . . . . .
O2 O 1.09962(19) 0.21441(17) 0.94304(14) 0.0522(3) Uani 1 1 d . . . . .
N3 N 1.14650(18) 0.35311(18) 0.93453(12) 0.0333(3) Uani 1 1 d . . . . .
C4 C 1.03837(19) 0.38023(18) 0.82992(13) 0.0269(3) Uani 1 1 d . . . . .
C5 C 0.85099(18) 0.28617(17) 0.75663(13) 0.0246(3) Uani 1 1 d . . . . .
N6 N 0.70759(17) 0.14718(16) 0.77331(13) 0.0319(3) Uani 1 1 d . . . . .
O7 O 0.70569(18) 0.13289(18) 0.88353(12) 0.0504(3) Uani 1 1 d . . . . .
O8 O 0.58892(18) 0.04784(14) 0.67477(12) 0.0457(3) Uani 1 1 d . . . . .
C9 C 0.83306(18) 0.36368(17) 0.66262(13) 0.0242(3) Uani 1 1 d . . . . .
N10 N 1.00111(16) 0.49217(15) 0.68053(12) 0.0308(3) Uani 1 1 d . . . . .
N11 N 1.12752(17) 0.50121(16) 0.78393(12) 0.0326(3) Uani 1 1 d . . . . .
C12 C 0.67018(18) 0.33245(16) 0.56041(13) 0.0238(3) Uani 1 1 d . . . . .
C13 C 0.46839(18) 0.27825(17) 0.55118(13) 0.0252(3) Uani 1 1 d . . . . .
N14 N 0.36205(17) 0.23103(17) 0.64965(12) 0.0344(3) Uani 1 1 d . . . . .
O15 O 0.43697(17) 0.30964(18) 0.76512(11) 0.0497(3) Uani 1 1 d . . . . .
O16 O 0.20710(18) 0.11587(19) 0.61379(14) 0.0587(4) Uani 1 1 d . . . . .
C17 C 0.39595(18) 0.27686(16) 0.42639(13) 0.0260(3) Uani 1 1 d . . . . .
N18 N 0.19560(17) 0.23203(16) 0.36251(13) 0.0332(3) Uani 1 1 d . . . . .
O19 O 0.07454(16) 0.24169(16) 0.43199(13) 0.0459(3) Uani 1 1 d . . . . .
O20 O 0.16234(18) 0.1891(2) 0.24205(12) 0.0574(4) Uani 1 1 d . . . . .
N21 N 0.53627(16) 0.32711(15) 0.36153(11) 0.0288(2) Uani 1 1 d . . . . .
N22 N 0.70079(16) 0.35880(15) 0.44406(11) 0.0276(2) Uani 1 1 d . . . . .
H22 H 0.8153 0.3927 0.4248 0.033 Uiso 1 1 calc R U . . .
K23 K 0.48564(5) 0.23708(5) 1.07756(3) 0.04334(11) Uani 1 1 d . . . . .
O24 O 0.72158(18) 0.06610(18) 1.13913(14) 0.0522(3) Uani 1 1 d D . . . .
H24A H 0.8370(17) 0.108(3) 1.138(2) 0.078 Uiso 1 1 d D U . . .
H24B H 0.721(3) 0.039(3) 1.2061(17) 0.078 Uiso 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.2212(18) . ?
O2 N3 1.2198(18) . ?
N3 C4 1.4439(17) . ?
C4 N11 1.3220(18) . ?
C4 C5 1.3964(18) . ?
C5 C9 1.3947(18) . ?
C5 N6 1.4203(17) . ?
N6 O7 1.2238(16) . ?
N6 O8 1.2332(17) . ?
C9 N10 1.3517(17) . ?
C9 C12 1.4569(17) . ?
N10 N11 1.3563(16) . ?
C12 N22 1.3543(17) . ?
C12 C13 1.3899(17) . ?
C13 C17 1.3960(18) . ?
C13 N14 1.4374(17) . ?
N14 O16 1.2157(17) . ?
N14 O15 1.2275(17) . ?
C17 N21 1.3173(18) . ?
C17 N18 1.4521(17) . ?
N18 O19 1.2148(17) . ?
N18 O20 1.2238(17) . ?
N21 N22 1.3413(15) . ?
N22 H22 0.8600 . ?
O24 H24A 0.811(10) . ?
O24 H24B 0.818(9) . ?

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
O2 N3 O1 123.58(13) . . ?
O2 N3 C4 118.55(13) . . ?
O1 N3 C4 117.82(13) . . ?
N11 C4 C5 111.36(12) . . ?
N11 C4 N3 118.83(12) . . ?
C5 C4 N3 129.50(13) . . ?
C9 C5 C4 103.46(11) . . ?
C9 C5 N6 127.08(12) . . ?
C4 C5 N6 129.44(12) . . ?
O7 N6 O8 123.44(13) . . ?
O7 N6 C5 119.04(13) . . ?
O8 N6 C5 117.51(12) . . ?
N10 C9 C5 108.79(11) . . ?
N10 C9 C12 119.59(11) . . ?
C5 C9 C12 131.57(12) . . ?
C9 N10 N11 109.12(11) . . ?
C4 N11 N10 107.25(11) . . ?
N22 C12 C13 104.77(11) . . ?
N22 C12 C9 121.14(11) . . ?
C13 C12 C9 134.08(12) . . ?
C12 C13 C17 104.96(11) . . ?
C12 C13 N14 126.25(12) . . ?
C17 C13 N14 128.77(12) . . ?
O16 N14 O15 124.60(13) . . ?
O16 N14 C13 118.42(13) . . ?
O15 N14 C13 116.96(12) . . ?
N21 C17 C13 112.35(11) . . ?
N21 C17 N18 117.84(12) . . ?
C13 C17 N18 129.81(12) . . ?
O19 N18 O20 124.96(13) . . ?
O19 N18 C17 117.95(12) . . ?
O20 N18 C17 117.08(12) . . ?
C17 N21 N22 104.05(11) . . ?
N21 N22 C12 113.87(11) . . ?
N21 N22 H22 123.1 . . ?
C12 N22 H22 123.1 . . ?
H24A O24 H24B 103.4(18) . . ?

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
O2 N3 C4 N11 -151.99(14) . . . . ?
O1 N3 C4 N11 25.44(19) . . . . ?
O2 N3 C4 C5 21.0(2) . . . . ?
O1 N3 C4 C5 -161.55(15) . . . . ?
N11 C4 C5 C9 -1.07(16) . . . . ?
N3 C4 C5 C9 -174.49(13) . . . . ?
N11 C4 C5 N6 -179.54(14) . . . . ?
N3 C4 C5 N6 7.0(2) . . . . ?
C9 C5 N6 O7 -149.93(15) . . . . ?
C4 C5 N6 O7 28.2(2) . . . . ?
C9 C5 N6 O8 29.0(2) . . . . ?
C4 C5 N6 O8 -152.84(15) . . . . ?
C4 C5 C9 N10 0.84(15) . . . . ?
N6 C5 C9 N10 179.36(13) . . . . ?
C4 C5 C9 C12 -176.46(14) . . . . ?
N6 C5 C9 C12 2.1(2) . . . . ?
C5 C9 N10 N11 -0.36(16) . . . . ?
C12 C9 N10 N11 177.31(12) . . . . ?
C5 C4 N11 N10 0.88(17) . . . . ?
N3 C4 N11 N10 175.09(12) . . . . ?
C9 N10 N11 C4 -0.32(16) . . . . ?
N10 C9 C12 N22 36.19(19) . . . . ?
C5 C9 C12 N22 -146.75(15) . . . . ?
N10 C9 C12 C13 -142.74(16) . . . . ?
C5 C9 C12 C13 34.3(3) . . . . ?
N22 C12 C13 C17 0.23(15) . . . . ?
C9 C12 C13 C17 179.28(14) . . . . ?
N22 C12 C13 N14 178.86(13) . . . . ?
C9 C12 C13 N14 -2.1(3) . . . . ?
C12 C13 N14 O16 -142.46(16) . . . . ?
C17 C13 N14 O16 35.9(2) . . . . ?
C12 C13 N14 O15 36.5(2) . . . . ?
C17 C13 N14 O15 -145.15(15) . . . . ?
C12 C13 C17 N21 -0.78(16) . . . . ?
N14 C13 C17 N21 -179.36(14) . . . . ?
C12 C13 C17 N18 -179.64(14) . . . . ?
N14 C13 C17 N18 1.8(2) . . . . ?
N21 C17 N18 O19 -154.66(14) . . . . ?
C13 C17 N18 O19 24.2(2) . . . . ?
N21 C17 N18 O20 24.5(2) . . . . ?
C13 C17 N18 O20 -156.70(16) . . . . ?
C13 C17 N21 N22 0.97(16) . . . . ?
N18 C17 N21 N22 179.98(12) . . . . ?
C17 N21 N22 C12 -0.83(16) . . . . ?
C13 C12 N22 N21 0.37(16) . . . . ?
C9 C12 N22 N21 -178.83(12) . . . . ?

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
N22 H22 N10 0.86 2.04 2.8154(16) 150.2 2_766
N22 H22 N11 0.86 2.67 3.2085(17) 121.5 2_766
O24 H24A O20 0.811(10) 2.345(15) 3.0661(17) 149(2) 1_656

_refine_diff_density_max         0.307
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.048

# start Validation Reply Form
_vrf_PLAT015_shrv587             
;
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.
;
####################################################################### 
# 
# 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_shrv583
_database_code_depnum_ccdc_archive 'CCDC 1811784'
_audit_update_record             
;
2017-12-16 deposited with the CCDC.
2018-03-01 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 N8 O8, 2(C H7 N4)'
_chemical_formula_sum            'C8 H14 N16 O8'
_chemical_formula_weight         462.35

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           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

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

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

_cell_length_a                   6.7723(10)
_cell_length_b                   10.2479(15)
_cell_length_c                   13.471(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.860(5)
_cell_angle_gamma                90
_cell_volume                     907.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2414
_cell_measurement_theta_min      3.117
_cell_measurement_theta_max      25.619

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.149
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7035
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            10605
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.115
_diffrn_reflns_theta_max         30.010
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2582
_reflns_number_gt                1735
_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 APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_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)+(0.0730P)²+0.0218P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2582
_refine_ls_number_parameters     151
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1273
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
O1 O 0.5050(2) 0.65888(11) 0.32249(12) 0.0685(4) Uani 1 1 d . . . . .
O2 O 0.82116(19) 0.71587(12) 0.36102(9) 0.0511(3) Uani 1 1 d . . . . .
N3 N 0.6390(2) 0.74192(11) 0.33755(9) 0.0366(3) Uani 1 1 d . . . . .
C4 C 0.5813(2) 0.87633(12) 0.32548(10) 0.0276(3) Uani 1 1 d . . . . .
C5 C 0.4346(2) 0.94223(13) 0.36381(10) 0.0295(3) Uani 1 1 d . . . . .
N6 N 0.29759(19) 0.89647(12) 0.42255(9) 0.0347(3) Uani 1 1 d . . . . .
O7 O 0.31159(19) 0.78236(11) 0.45125(9) 0.0511(3) Uani 1 1 d . . . . .
O8 O 0.17534(19) 0.97368(13) 0.44345(10) 0.0543(3) Uani 1 1 d . . . . .
N9 N 0.43963(18) 1.06909(11) 0.34467(9) 0.0341(3) Uani 1 1 d . . . . .
N10 N 0.58197(18) 1.08939(11) 0.29178(9) 0.0341(3) Uani 1 1 d . . . . .
C11 C 0.6720(2) 0.97445(12) 0.27916(9) 0.0276(3) Uani 1 1 d . . . . .
N12 N -0.0367(2) 0.28117(14) 0.39788(12) 0.0476(4) Uani 1 1 d D . . . .
H12A H -0.105(3) 0.2341(18) 0.3437(10) 0.071 Uiso 1 1 d D U . . .
N13 N 0.1677(2) 0.27662(11) 0.39215(10) 0.0390(3) Uani 1 1 d . . . . .
H13 H 0.2297 0.2031 0.3937 0.047 Uiso 1 1 calc R U . . .
C14 C 0.2625(2) 0.38710(13) 0.38434(11) 0.0349(3) Uani 1 1 d . . . . .
N15 N 0.4501(2) 0.38299(14) 0.37037(12) 0.0511(4) Uani 1 1 d . . . . .
H15A H 0.5078 0.3090 0.3666 0.061 Uiso 1 1 calc R U . . .
H15B H 0.5137 0.4543 0.3651 0.061 Uiso 1 1 calc R U . . .
N16 N 0.1718(2) 0.49968(12) 0.39148(12) 0.0512(4) Uani 1 1 d . . . . .
H16A H 0.0508 0.5009 0.4012 0.061 Uiso 1 1 calc R U . . .
H16B H 0.2337 0.5718 0.3864 0.061 Uiso 1 1 calc R U . . .
H12B H -0.041(3) 0.243(2) 0.4581(9) 0.077 Uiso 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.2252(17) . ?
O2 N3 1.2274(17) . ?
N3 C4 1.4304(17) . ?
C4 C5 1.3984(18) . ?
C4 C11 1.4003(18) . ?
C5 N9 1.3274(18) . ?
C5 N6 1.4348(18) . ?
N6 O8 1.2258(16) . ?
N6 O7 1.2281(16) . ?
N9 N10 1.3451(16) . ?
N10 C11 1.3554(17) . ?
C11 C11 1.460(3) 2_655 ?
N12 N13 1.4054(19) . ?
N12 H12A 0.905(9) . ?
N12 H12B 0.905(9) . ?
N13 C14 1.3182(18) . ?
N13 H13 0.8600 . ?
C14 N16 1.3215(18) . ?
C14 N15 1.328(2) . ?
N15 H15A 0.8600 . ?
N15 H15B 0.8600 . ?
N16 H16A 0.8600 . ?
N16 H16B 0.8600 . ?

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 N3 O2 123.41(13) . . ?
O1 N3 C4 118.60(13) . . ?
O2 N3 C4 117.98(12) . . ?
C5 C4 C11 104.12(11) . . ?
C5 C4 N3 128.46(12) . . ?
C11 C4 N3 127.24(12) . . ?
N9 C5 C4 110.34(11) . . ?
N9 C5 N6 118.52(12) . . ?
C4 C5 N6 131.02(12) . . ?
O8 N6 O7 123.21(13) . . ?
O8 N6 C5 118.51(12) . . ?
O7 N6 C5 118.26(12) . . ?
C5 N9 N10 108.03(11) . . ?
N9 N10 C11 109.44(11) . . ?
N10 C11 C4 108.05(12) . . ?
N10 C11 C11 118.20(8) . 2_655 ?
C4 C11 C11 133.70(8) . 2_655 ?
N13 N12 H12A 105.2(14) . . ?
N13 N12 H12B 106.0(15) . . ?
H12A N12 H12B 112.0(16) . . ?
C14 N13 N12 118.75(12) . . ?
C14 N13 H13 120.6 . . ?
N12 N13 H13 120.6 . . ?
N13 C14 N16 120.00(15) . . ?
N13 C14 N15 119.00(13) . . ?
N16 C14 N15 120.99(13) . . ?
C14 N15 H15A 120.0 . . ?
C14 N15 H15B 120.0 . . ?
H15A N15 H15B 120.0 . . ?
C14 N16 H16A 120.0 . . ?
C14 N16 H16B 120.0 . . ?
H16A N16 H16B 120.0 . . ?

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 N3 C4 C5 47.5(2) . . . . ?
O2 N3 C4 C5 -133.66(15) . . . . ?
O1 N3 C4 C11 -138.29(15) . . . . ?
O2 N3 C4 C11 40.59(19) . . . . ?
C11 C4 C5 N9 -1.44(15) . . . . ?
N3 C4 C5 N9 173.84(13) . . . . ?
C11 C4 C5 N6 -177.19(13) . . . . ?
N3 C4 C5 N6 -1.9(2) . . . . ?
N9 C5 N6 O8 7.69(19) . . . . ?
C4 C5 N6 O8 -176.85(13) . . . . ?
N9 C5 N6 O7 -170.80(13) . . . . ?
C4 C5 N6 O7 4.7(2) . . . . ?
C4 C5 N9 N10 1.80(15) . . . . ?
N6 C5 N9 N10 178.15(11) . . . . ?
C5 N9 N10 C11 -1.43(15) . . . . ?
N9 N10 C11 C4 0.52(15) . . . . ?
N9 N10 C11 C11 178.31(13) . . . 2_655 ?
C5 C4 C11 N10 0.54(14) . . . . ?
N3 C4 C11 N10 -174.82(13) . . . . ?
C5 C4 C11 C11 -176.77(18) . . . 2_655 ?
N3 C4 C11 C11 7.9(3) . . . 2_655 ?
N12 N13 C14 N16 6.2(2) . . . . ?
N12 N13 C14 N15 -174.47(15) . . . . ?

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
N13 H13 O8 0.86 2.50 3.1782(19) 136.8 1_545
N13 H13 N9 0.86 2.19 2.9814(17) 152.9 1_545
N16 H16B O7 0.86 2.34 3.0938(18) 146.4 .
N16 H16B O1 0.86 2.38 3.1019(19) 141.6 .
N15 H15A O7 0.86 2.64 3.0648(19) 111.9 3_666
N15 H15A N10 0.86 2.56 3.3802(18) 158.7 1_545
N15 H15A N9 0.86 2.51 3.2344(19) 143.0 1_545
N15 H15B O1 0.86 2.17 2.9432(18) 149.3 .
N12 H12A N10 0.905(9) 2.542(15) 3.2872(19) 140.1(16) 1_445
N12 H12A N10 0.905(9) 2.387(14) 3.1795(19) 146.3(18) 2_545
N12 H12B O2 0.905(9) 2.567(16) 3.226(2) 130.2(16) 3_666
N12 H12B O7 0.905(9) 2.450(18) 3.1357(19) 132.8(18) 3_566

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.053

# start Validation Reply Form
_vrf_PLAT015_shrv583             
;
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.
;
####################################################################### 
# 
# 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_shrv582_c
_database_code_depnum_ccdc_archive 'CCDC 1811783'
_audit_update_record             
;
2017-12-16 deposited with the CCDC.
2018-03-01 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 N8 O8, 2(H5 N2), H2 O'
_chemical_formula_sum            'C6 H12 N12 O9'
_chemical_formula_weight         396.28

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   24.534(7)
_cell_length_b                   3.7499(9)
_cell_length_c                   18.811(5)
_cell_angle_alpha                90
_cell_angle_beta                 122.434(6)
_cell_angle_gamma                90
_cell_volume                     1460.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1484
_cell_measurement_theta_min      3.353
_cell_measurement_theta_max      25.946

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.802
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.062
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.165
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4858
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            6763
_diffrn_reflns_av_unetI/netI     0.0749
_diffrn_reflns_av_R_equivalents  0.0764
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.936
_diffrn_reflns_theta_max         28.314
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1784
_reflns_number_gt                981
_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 APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_special_details          
;
Whole-molecule two-component disorder observed for cation and anion with a 
85:15 ratio between major and minor components.  Bond lengths and angles 
of minor component restrained to corresponding values in major component.
Minor component thermal displacement parameters were refined isotropically.  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0714P)²+3.5558P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1784
_refine_ls_number_parameters     183
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.1332
_refine_ls_R_factor_gt           0.0665
_refine_ls_wR_factor_ref         0.1835
_refine_ls_wR_factor_gt          0.1527
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.014
_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
O1A O 0.9870(2) 0.522(4) 0.5981(6) 0.0550(13) Uani 0.851(3) 1 d D . P A 1
O2A O 0.92139(15) 0.7770(9) 0.4801(2) 0.0539(9) Uani 0.851(3) 1 d D . P A 1
N3A N 0.93267(16) 0.5832(10) 0.5390(3) 0.0338(11) Uani 0.851(3) 1 d D . P A 1
C4A C 0.87907(17) 0.4423(10) 0.5398(2) 0.0277(10) Uani 0.851(3) 1 d D . P A 1
C5A C 0.81375(16) 0.4360(10) 0.4769(2) 0.0236(9) Uani 0.851(3) 1 d D . P A 1
N6A N 0.7874(3) 0.522(2) 0.3904(3) 0.0274(8) Uani 0.851(3) 1 d D . P A 1
O7A O 0.81214(19) 0.4019(12) 0.3548(2) 0.0605(11) Uani 0.851(3) 1 d D . P A 1
O8A O 0.74220(13) 0.7379(8) 0.35694(18) 0.0458(8) Uani 0.851(3) 1 d D . P A 1
C9A C 0.78418(15) 0.2898(9) 0.5164(2) 0.0238(8) Uani 0.851(3) 1 d D . P A 1
N10A N 0.83039(13) 0.2164(8) 0.59783(18) 0.0272(7) Uani 0.851(3) 1 d D . P A 1
N11A N 0.88878(13) 0.3167(9) 0.61184(19) 0.0290(7) Uani 0.851(3) 1 d D . P A 1
O1B O 0.9888(14) 0.53(2) 0.597(3) 0.050 Uiso 0.149(3) 1 d D U P A 2
O2B O 0.9235(8) 0.240(5) 0.4861(12) 0.050 Uiso 0.149(3) 1 d D U P A 2
N3B N 0.9342(11) 0.474(9) 0.538(2) 0.050 Uiso 0.149(3) 1 d D U P A 2
C4B C 0.8800(10) 0.569(9) 0.5421(15) 0.050 Uiso 0.149(3) 1 d D U P A 2
C5B C 0.8146(11) 0.558(9) 0.4794(13) 0.050 Uiso 0.149(3) 1 d D U P A 2
N6B N 0.785(2) 0.497(17) 0.3910(17) 0.050 Uiso 0.149(3) 1 d D U P A 2
O7B O 0.8098(10) 0.598(6) 0.3538(13) 0.050 Uiso 0.149(3) 1 d D U P A 2
O8B O 0.7430(8) 0.256(5) 0.3579(11) 0.050 Uiso 0.149(3) 1 d D U P A 2
C9B C 0.7854(9) 0.723(7) 0.5179(13) 0.050 Uiso 0.149(3) 1 d D U P A 2
N10B N 0.8312(8) 0.817(6) 0.5975(12) 0.050 Uiso 0.149(3) 1 d D U P A 2
N11B N 0.8895(8) 0.717(6) 0.6127(12) 0.050 Uiso 0.149(3) 1 d D U P A 2
N12 N 0.60794(14) 0.7170(9) 0.2488(2) 0.0338(8) Uani 0.851(3) 1 d . . P A 1
H12A H 0.6395 0.6792 0.3021 0.051 Uiso 0.851(3) 1 calc R U P A 1
H12B H 0.5699 0.6973 0.2440 0.051 Uiso 0.851(3) 1 calc DR U P A 1
H12C H 0.6118 0.9350 0.2333 0.051 Uiso 0.851(3) 1 calc R U P A 1
N13A N 0.61196(17) 0.4609(13) 0.1962(3) 0.0317(11) Uani 0.851(3) 1 d D . P A 1
H13A H 0.6476(12) 0.499(14) 0.194(3) 0.058(16) Uiso 0.851(3) 1 d D . P A 1
H13B H 0.5760(11) 0.501(12) 0.1448(14) 0.051(15) Uiso 0.851(3) 1 d D . P A 1
N12B N 0.629(2) 0.432(12) 0.202(3) 0.050 Uiso 0.149(3) 1 d D U P A 2
H12E H 0.6658 0.3499 0.2105 0.075 Uiso 0.149(3) 1 calc R U P A 2
H12F H 0.6344 0.6541 0.2216 0.075 Uiso 0.149(3) 1 calc R U P A 2
H12G H 0.5986 0.4284 0.1476 0.075 Uiso 0.149(3) 1 calc R U P A 2
N13B N 0.6090(10) 0.210(6) 0.2466(15) 0.050 Uiso 0.149(3) 1 d D U P A 2
H13C H 0.623(3) 0.321(18) 0.296(2) 0.075 Uiso 0.149(3) 1 d D U P A 2
H13D H 0.5653(12) 0.200(19) 0.214(3) 0.075 Uiso 0.149(3) 1 d D U P A 2
O14 O 0.5000 0.4819(10) 0.2500 0.0388(8) Uani 1 2 d DS T P . .
H14 H 0.5241(11) 0.345(9) 0.289(2) 0.074(16) Uiso 1 1 d 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
O1A N3A 1.214(7) . ?
O2A N3A 1.226(5) . ?
N3A C4A 1.425(5) . ?
C4A N11A 1.329(5) . ?
C4A C5A 1.391(4) . ?
C5A C9A 1.399(5) . ?
C5A N6A 1.429(5) . ?
N6A O7A 1.208(7) . ?
N6A O8A 1.237(10) . ?
C9A N10A 1.358(4) . ?
C9A C9A 1.474(7) 7_656 ?
N10A N11A 1.363(4) . ?
O1B N3B 1.217(18) . ?
O2B N3B 1.231(18) . ?
N3B C4B 1.419(17) . ?
C4B N11B 1.339(17) . ?
C4B C5B 1.392(17) . ?
C5B C9B 1.407(18) . ?
C5B N6B 1.431(16) . ?
N6B O7B 1.212(17) . ?
N6B O8B 1.25(2) . ?
C9B N10B 1.351(17) . ?
C9B C9B 1.50(4) 7_666 ?
N10B N11B 1.352(17) . ?
N12 N13A 1.420(6) . ?
N12 H12A 0.8900 . ?
N12 H12B 0.8900 . ?
N12 H12C 0.8900 . ?
N13A H13A 0.910(10) . ?
N13A H13B 0.907(10) . ?
N12B N13B 1.433(10) . ?
N12B H12E 0.8900 . ?
N12B H12F 0.8900 . ?
N12B H12G 0.8900 . ?
N13B H13C 0.908(11) . ?
N13B H13D 0.908(10) . ?
O14 H14 0.829(10) . ?

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
O2A N3A O1A 122.9(8) . . ?
O2A N3A C4A 117.9(3) . . ?
O1A N3A C4A 119.1(8) . . ?
N11A C4A C5A 110.8(3) . . ?
N11A C4A N3A 118.7(3) . . ?
C5A C4A N3A 130.2(4) . . ?
C4A C5A C9A 104.1(3) . . ?
C4A C5A N6A 125.2(3) . . ?
C9A C5A N6A 130.2(3) . . ?
O7A N6A O8A 122.8(4) . . ?
O7A N6A C5A 119.5(7) . . ?
O8A N6A C5A 117.6(5) . . ?
N10A C9A C5A 108.7(3) . . ?
N10A C9A C9A 120.3(4) . 7_656 ?
C5A C9A C9A 130.9(4) . 7_656 ?
C9A N10A N11A 108.5(3) . . ?
C4A N11A N10A 107.8(3) . . ?
O2B N3B O1B 121(3) . . ?
O2B N3B C4B 115(2) . . ?
O1B N3B C4B 121(3) . . ?
N11B C4B C5B 111.2(14) . . ?
N11B C4B N3B 119.3(17) . . ?
C5B C4B N3B 129.3(18) . . ?
C4B C5B C9B 102.9(14) . . ?
C4B C5B N6B 129(2) . . ?
C9B C5B N6B 126(3) . . ?
O7B N6B O8B 118(2) . . ?
O7B N6B C5B 121(2) . . ?
O8B N6B C5B 118(3) . . ?
N10B C9B C5B 109.6(15) . . ?
N10B C9B C9B 122(2) . 7_666 ?
C5B C9B C9B 128(2) . 7_666 ?
C9B N10B N11B 108.6(15) . . ?
C4B N11B N10B 107.6(15) . . ?
N13A N12 H12A 109.5 . . ?
N13A N12 H12B 109.5 . . ?
H12A N12 H12B 109.5 . . ?
N13A N12 H12C 109.5 . . ?
H12A N12 H12C 109.5 . . ?
H12B N12 H12C 109.5 . . ?
N12 N13A H13A 111(3) . . ?
N12 N13A H13B 104(3) . . ?
H13A N13A H13B 110(2) . . ?
N13B N12B H12E 109.5 . . ?
N13B N12B H12F 109.5 . . ?
H12E N12B H12F 109.5 . . ?
N13B N12B H12G 109.5 . . ?
H12E N12B H12G 109.5 . . ?
H12F N12B H12G 109.5 . . ?
N12B N13B H13C 106.4(14) . . ?
N12B N13B H13D 106.4(14) . . ?
H13C N13B H13D 111(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
O2A N3A C4A N11A -161.8(4) . . . . ?
O1A N3A C4A N11A 14.5(8) . . . . ?
O2A N3A C4A C5A 12.4(7) . . . . ?
O1A N3A C4A C5A -171.3(7) . . . . ?
N11A C4A C5A C9A -0.9(4) . . . . ?
N3A C4A C5A C9A -175.4(4) . . . . ?
N11A C4A C5A N6A -174.1(5) . . . . ?
N3A C4A C5A N6A 11.3(7) . . . . ?
C4A C5A N6A O7A 45.6(8) . . . . ?
C9A C5A N6A O7A -125.8(5) . . . . ?
C4A C5A N6A O8A -129.9(4) . . . . ?
C9A C5A N6A O8A 58.8(7) . . . . ?
C4A C5A C9A N10A 0.0(4) . . . . ?
N6A C5A C9A N10A 172.8(6) . . . . ?
C4A C5A C9A C9A -179.4(5) . . . 7_656 ?
N6A C5A C9A C9A -6.7(9) . . . 7_656 ?
C5A C9A N10A N11A 0.8(4) . . . . ?
C9A C9A N10A N11A -179.7(4) 7_656 . . . ?
C5A C4A N11A N10A 1.5(4) . . . . ?
N3A C4A N11A N10A 176.7(3) . . . . ?
C9A N10A N11A C4A -1.4(4) . . . . ?
O2B N3B C4B N11B 157(3) . . . . ?
O1B N3B C4B N11B -2(8) . . . . ?
O2B N3B C4B C5B -29(6) . . . . ?
O1B N3B C4B C5B 172(6) . . . . ?
N11B C4B C5B C9B 2(4) . . . . ?
N3B C4B C5B C9B -173(4) . . . . ?
N11B C4B C5B N6B 165(4) . . . . ?
N3B C4B C5B N6B -10(7) . . . . ?
C4B C5B N6B O7B -33(9) . . . . ?
C9B C5B N6B O7B 126(5) . . . . ?
C4B C5B N6B O8B 127(5) . . . . ?
C9B C5B N6B O8B -73(7) . . . . ?
C4B C5B C9B N10B -1(4) . . . . ?
N6B C5B C9B N10B -164(3) . . . . ?
C4B C5B C9B C9B -177(4) . . . 7_666 ?
N6B C5B C9B C9B 19(6) . . . 7_666 ?
C5B C9B N10B N11B 0(3) . . . . ?
C9B C9B N10B N11B 177(3) 7_666 . . . ?
C5B C4B N11B N10B -2(4) . . . . ?
N3B C4B N11B N10B 174(3) . . . . ?
C9B N10B N11B C4B 1(3) . . . . ?

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
N12 H12A O8A 0.89 2.16 2.794(4) 127.5 .
N12 H12A N10A 0.89 2.19 2.928(4) 139.8 7_656
N12 H12B O14 0.89 1.95 2.802(4) 158.9 .
N13A H13A O7A 0.910(10) 2.25(3) 3.007(5) 140(4) 4_655
N13A H13B O1A 0.907(10) 2.58(4) 3.240(10) 130(4) 8_465
N13A H13B O2A 0.907(10) 2.53(4) 3.039(6) 116(3) 4_645
N12B H12E O7B 0.89 1.87 2.58(5) 135.6 4_645
N12B H12E O8B 0.89 2.40 2.84(5) 110.3 .
N12B H12G O2B 0.89 2.55 3.27(4) 137.7 4_655
N13B H13C N10B 0.908(11) 2.16(4) 3.05(3) 163(4) 7_666
N13B H13C N11B 0.908(11) 2.56(6) 3.39(3) 153(7) 7_666
N13B H13D O1B 0.908(10) 2.18(7) 2.93(5) 140(6) 8_455
N13B H13D O14 0.908(10) 2.30(5) 2.90(2) 123(5) .
O14 H14 N11A 0.829(10) 2.034(17) 2.801(3) 154(3) 7_656

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.068

# start Validation Reply Form
_vrf_PLAT015_shrv582_c           
;
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.
;
