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

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

data_shrv686
_database_code_depnum_ccdc_archive 'CCDC 1860646'
_audit_update_record             
;
2018-08-07 deposited with the CCDC.
2018-10-30 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         'C5 N8 O9, K, N2 H5'
_chemical_formula_sum            'C5 H5 K N10 O9'
_chemical_formula_weight         388.29

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      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                   7.7155(2)
_cell_length_b                   10.5198(2)
_cell_length_c                   16.7965(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.9850(10)
_cell_angle_gamma                90
_cell_volume                     1338.32(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5699
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      28.81

_exptl_crystal_description       block
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.927
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.082
_exptl_absorpt_coefficient_mu    0.478
_shelx_estimated_absorpt_T_min   0.907
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7045
_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            15653
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.296
_diffrn_reflns_theta_max         30.089
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3815
_reflns_number_gt                3098
_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          
;
The hydrazinium cation displays two-component disorder.  Occupancies 
of the major and minor component were refined using a free variable.  
Bond angles and lengths for both disorder components were restrained to 
literature values.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+0.3525P] 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         3815
_refine_ls_number_parameters     259
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0775
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.005
_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 0.11145(12) 0.01512(8) 0.58105(6) 0.0351(2) Uani 1 1 d . . . . .
O2 O -0.03019(12) 0.19276(9) 0.55230(6) 0.0351(2) Uani 1 1 d . . . . .
N3 N 0.10888(13) 0.12824(10) 0.56082(6) 0.0270(2) Uani 1 1 d . . . . .
C4 C 0.25755(16) 0.19166(11) 0.54595(8) 0.0271(2) Uani 1 1 d . . . . .
N5 N 0.42301(14) 0.13694(10) 0.55979(7) 0.0307(2) Uani 1 1 d . . . . .
O6 O 0.45398(13) 0.03131(10) 0.59228(8) 0.0492(3) Uani 1 1 d . . . . .
O7 O 0.54442(12) 0.20170(9) 0.54048(7) 0.0397(2) Uani 1 1 d . . . . .
C8 C 0.23898(15) 0.32215(11) 0.51827(8) 0.0267(2) Uani 1 1 d . . . . .
N9 N 0.12746(14) 0.35373(10) 0.45110(7) 0.0310(2) Uani 1 1 d . . . . .
O10 O 0.02431(13) 0.29437(10) 0.39937(6) 0.0416(2) Uani 1 1 d . . . . .
O11 O 0.13286(13) 0.48981(9) 0.44220(6) 0.0380(2) Uani 1 1 d . . . . .
N12 N 0.25629(15) 0.53560(11) 0.50521(7) 0.0351(3) Uani 1 1 d . . . . .
C13 C 0.31874(16) 0.43809(11) 0.54991(8) 0.0283(2) Uani 1 1 d . . . . .
C14 C 0.45520(17) 0.46182(11) 0.62144(8) 0.0290(3) Uani 1 1 d . . . . .
N15 N 0.51635(19) 0.37435(11) 0.67361(8) 0.0434(3) Uani 1 1 d . . . . .
O16 O 0.64583(16) 0.44098(9) 0.72955(6) 0.0457(3) Uani 1 1 d . . . . .
C17 C 0.64425(18) 0.56270(12) 0.70254(8) 0.0318(3) Uani 1 1 d . . . . .
N18 N 0.52715(14) 0.58053(10) 0.63596(7) 0.0308(2) Uani 1 1 d . . . . .
N19 N 0.77004(17) 0.63417(11) 0.74919(7) 0.0391(3) Uani 1 1 d . . . . .
N20 N 0.77195(16) 0.75721(11) 0.73031(7) 0.0373(3) Uani 1 1 d . . . . .
O21 O 0.66070(14) 0.81009(9) 0.67804(7) 0.0444(3) Uani 1 1 d . . . . .
O22 O 0.89723(17) 0.81888(11) 0.77030(8) 0.0583(3) Uani 1 1 d . . . . .
K23 K 0.30934(4) 0.79665(3) 0.59691(2) 0.03897(9) Uani 1 1 d . . . . .
N24A N 0.7683(11) 0.1127(11) 0.7438(5) 0.093(2) Uani 0.482(15) 1 d D U P A 1
H24A H 0.858(4) 0.162(5) 0.771(2) 0.140 Uiso 0.482(15) 1 d D U P A 1
H24B H 0.751(8) 0.045(3) 0.775(2) 0.140 Uiso 0.482(15) 1 d D U P A 1
N25A N 0.8393(14) 0.0593(6) 0.6814(5) 0.053(2) Uani 0.482(15) 1 d D U P A 1
H25A H 0.9557 0.0707 0.6913 0.080 Uiso 0.482(15) 1 calc R U P A 1
H25B H 0.7922 0.0964 0.6347 0.080 Uiso 0.482(15) 1 calc R U P A 1
H25C H 0.8155 -0.0236 0.6784 0.080 Uiso 0.482(15) 1 calc R U P A 1
N24B N 0.7731(7) 0.1640(7) 0.7265(3) 0.0566(13) Uani 0.518(15) 1 d D U P A 2
H24C H 0.857(3) 0.226(2) 0.727(2) 0.085 Uiso 0.518(15) 1 d D U P A 2
H24D H 0.672(3) 0.196(3) 0.6946(17) 0.085 Uiso 0.518(15) 1 d D U P A 2
N25B N 0.8251(13) 0.0709(7) 0.6805(4) 0.057(2) Uani 0.518(15) 1 d D U P A 2
H25D H 0.9010 0.0197 0.7118 0.086 Uiso 0.518(15) 1 calc R U P A 2
H25E H 0.8772 0.1055 0.6428 0.086 Uiso 0.518(15) 1 calc R U P A 2
H25F H 0.7314 0.0264 0.6567 0.086 Uiso 0.518(15) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.2367(13) . ?
O2 N3 1.2546(13) . ?
N3 C4 1.3901(15) . ?
C4 N5 1.3791(16) . ?
C4 C8 1.4477(16) . ?
N5 O6 1.2410(14) . ?
N5 O7 1.2500(14) . ?
C8 N9 1.3242(16) . ?
C8 C13 1.4226(17) . ?
N9 O10 1.2307(15) . ?
N9 O11 1.4408(14) . ?
O11 N12 1.3693(15) . ?
N12 C13 1.3078(16) . ?
C13 C14 1.4601(19) . ?
C14 N15 1.2960(17) . ?
C14 N18 1.3695(15) . ?
N15 O16 1.4193(16) . ?
O16 C17 1.3577(16) . ?
C17 N18 1.3104(17) . ?
C17 N19 1.3533(18) . ?
N19 N20 1.3334(17) . ?
N20 O21 1.2369(16) . ?
N20 O22 1.2485(15) . ?
N24A N25A 1.389(7) . ?
N24A H24A 0.912(10) . ?
N24A H24B 0.910(10) . ?
N25A H25A 0.8900 . ?
N25A H25B 0.8900 . ?
N25A H25C 0.8900 . ?
N24B N25B 1.355(6) . ?
N24B H24C 0.921(10) . ?
N24B H24D 0.918(10) . ?
N25B H25D 0.8900 . ?
N25B H25E 0.8900 . ?
N25B H25F 0.8900 . ?

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 121.37(10) . . ?
O1 N3 C4 122.72(10) . . ?
O2 N3 C4 115.91(10) . . ?
N5 C4 N3 122.57(10) . . ?
N5 C4 C8 118.80(10) . . ?
N3 C4 C8 118.57(10) . . ?
O6 N5 O7 120.74(11) . . ?
O6 N5 C4 122.84(11) . . ?
O7 N5 C4 116.37(10) . . ?
N9 C8 C13 105.54(11) . . ?
N9 C8 C4 121.33(11) . . ?
C13 C8 C4 133.13(11) . . ?
O10 N9 C8 134.59(12) . . ?
O10 N9 O11 117.28(10) . . ?
C8 N9 O11 108.10(10) . . ?
N12 O11 N9 107.39(9) . . ?
C13 N12 O11 107.08(10) . . ?
N12 C13 C8 111.85(12) . . ?
N12 C13 C14 117.86(11) . . ?
C8 C13 C14 130.29(11) . . ?
N15 C14 N18 116.36(12) . . ?
N15 C14 C13 123.19(12) . . ?
N18 C14 C13 120.45(11) . . ?
C14 N15 O16 102.51(10) . . ?
C17 O16 N15 106.51(10) . . ?
N18 C17 N19 135.76(12) . . ?
N18 C17 O16 112.40(11) . . ?
N19 C17 O16 111.76(12) . . ?
C17 N18 C14 102.22(11) . . ?
N20 N19 C17 116.15(11) . . ?
O21 N20 O22 120.63(12) . . ?
O21 N20 N19 124.60(12) . . ?
O22 N20 N19 114.77(12) . . ?
N25A N24A H24A 104.1(18) . . ?
N25A N24A H24B 104.2(18) . . ?
H24A N24A H24B 109(2) . . ?
N24A N25A H25A 109.5 . . ?
N24A N25A H25B 109.5 . . ?
H25A N25A H25B 109.5 . . ?
N24A N25A H25C 109.5 . . ?
H25A N25A H25C 109.5 . . ?
H25B N25A H25C 109.5 . . ?
N25B N24B H24C 103.4(16) . . ?
N25B N24B H24D 103.8(16) . . ?
H24C N24B H24D 106(2) . . ?
N24B N25B H25D 109.5 . . ?
N24B N25B H25E 109.5 . . ?
H25D N25B H25E 109.5 . . ?
N24B N25B H25F 109.5 . . ?
H25D N25B H25F 109.5 . . ?
H25E N25B H25F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N3 C4 N5 -6.14(19) . . . . ?
O2 N3 C4 N5 174.02(11) . . . . ?
O1 N3 C4 C8 176.67(11) . . . . ?
O2 N3 C4 C8 -3.17(17) . . . . ?
N3 C4 N5 O6 -5.7(2) . . . . ?
C8 C4 N5 O6 171.44(13) . . . . ?
N3 C4 N5 O7 176.82(11) . . . . ?
C8 C4 N5 O7 -6.00(18) . . . . ?
N5 C4 C8 N9 124.89(13) . . . . ?
N3 C4 C8 N9 -57.81(17) . . . . ?
N5 C4 C8 C13 -56.3(2) . . . . ?
N3 C4 C8 C13 121.03(15) . . . . ?
C13 C8 N9 O10 179.94(13) . . . . ?
C4 C8 N9 O10 -0.9(2) . . . . ?
C13 C8 N9 O11 -1.97(13) . . . . ?
C4 C8 N9 O11 177.15(11) . . . . ?
O10 N9 O11 N12 -179.44(11) . . . . ?
C8 N9 O11 N12 2.09(13) . . . . ?
N9 O11 N12 C13 -1.26(13) . . . . ?
O11 N12 C13 C8 0.05(15) . . . . ?
O11 N12 C13 C14 179.49(11) . . . . ?
N9 C8 C13 N12 1.27(15) . . . . ?
C4 C8 C13 N12 -177.70(13) . . . . ?
N9 C8 C13 C14 -178.07(12) . . . . ?
C4 C8 C13 C14 3.0(2) . . . . ?
N12 C13 C14 N15 174.24(13) . . . . ?
C8 C13 C14 N15 -6.5(2) . . . . ?
N12 C13 C14 N18 -6.53(18) . . . . ?
C8 C13 C14 N18 172.78(12) . . . . ?
N18 C14 N15 O16 -0.61(16) . . . . ?
C13 C14 N15 O16 178.66(12) . . . . ?
C14 N15 O16 C17 0.10(15) . . . . ?
N15 O16 C17 N18 0.43(16) . . . . ?
N15 O16 C17 N19 -176.73(12) . . . . ?
N19 C17 N18 C14 175.48(16) . . . . ?
O16 C17 N18 C14 -0.74(15) . . . . ?
N15 C14 N18 C17 0.86(16) . . . . ?
C13 C14 N18 C17 -178.42(12) . . . . ?
N18 C17 N19 N20 7.6(2) . . . . ?
O16 C17 N19 N20 -176.12(12) . . . . ?
C17 N19 N20 O21 5.5(2) . . . . ?
C17 N19 N20 O22 -174.86(13) . . . . ?

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
N24A H24A O10 0.912(10) 2.33(3) 3.118(8) 144(4) 4_666
N24A H24A O22 0.912(10) 2.70(3) 3.413(8) 135(3) 2_746
N25A H25A O1 0.89 2.46 2.969(8) 116.6 1_655
N25A H25A N19 0.89 2.26 3.118(11) 161.5 2_746
N25A H25B O2 0.89 2.35 2.919(7) 121.5 1_655
N25A H25B O7 0.89 2.50 3.313(11) 152.7 .
N25A H25C N20 0.89 2.51 3.347(6) 156.8 1_545
N25A H25C O21 0.89 2.12 2.957(7) 156.8 1_545
N25A H25C O22 0.89 2.27 2.927(7) 130.3 1_545
N24B H24C O22 0.921(10) 2.123(15) 3.013(7) 162(3) 2_746
N24B H24D O7 0.918(10) 2.59(2) 3.306(5) 135(2) .
N24B H24D N15 0.918(10) 2.22(2) 2.989(5) 140(2) .
N24B H24D O16 0.918(10) 2.66(3) 3.078(6) 108(2) .
N25B H25D O22 0.89 2.33 3.049(8) 137.5 1_545
N25B H25E O1 0.89 2.44 3.069(8) 127.9 1_655
N25B H25E O2 0.89 2.02 2.905(7) 173.8 1_655
N25B H25E N3 0.89 2.47 3.298(7) 155.5 1_655
N25B H25F O6 0.89 2.21 2.992(10) 146.8 .
N25B H25F O21 0.89 2.38 3.020(8) 128.7 1_545

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.042

# start Validation Reply Form
_vrf_PLAT015_shrv686             
;
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_shrv691
_database_code_depnum_ccdc_archive 'CCDC 1860918'
_audit_update_record             
;
2018-08-07 deposited with the CCDC.
2018-10-30 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 N8 O9, K2'
_chemical_formula_sum            'C5 K2 N8 O9'
_chemical_formula_weight         394.33
_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'
K K 0.3868 1.0657 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2945(15)
_cell_length_b                   7.6721(16)
_cell_length_c                   12.581(3)
_cell_angle_alpha                95.648(8)
_cell_angle_beta                 95.017(8)
_cell_angle_gamma                117.937(8)
_cell_volume                     611.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2598
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.66
_cell_measurement_theta_min      6.64
_shelx_estimated_absorpt_T_max   0.560
_shelx_estimated_absorpt_T_min   0.197
_exptl_absorpt_coefficient_mu    7.639
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.4145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    2.141
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       chunk
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.246
_exptl_crystal_size_min          0.086
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7674
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.645
_diffrn_reflns_theta_min         3.572
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Photon 100'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'HELIOS multilayer optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   '1uS microfocus'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2317
_reflns_number_total             2437
_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       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0214(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2437
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+0.2854P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0794
_refine_special_details          ?
_atom_sites_solution_hydrogens   .
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.85877(19) 0.89820(19) 0.12980(11) 0.0339(3) Uani 1 1 d . . . . .
O2 O 0.5699(2) 0.78636(19) 0.01751(10) 0.0304(3) Uani 1 1 d . . . . .
N3 N 0.6669(2) 0.7736(2) 0.09927(11) 0.0229(3) Uani 1 1 d . . . . .
N5 N 0.3677(2) 0.4816(2) 0.13880(11) 0.0234(3) Uani 1 1 d . . . . .
C4 C 0.5769(2) 0.6262(2) 0.16153(12) 0.0226(3) Uani 1 1 d . . . . .
O6 O 0.24466(18) 0.4830(2) 0.06532(10) 0.0333(3) Uani 1 1 d . . . . .
C8 C 0.7070(2) 0.6156(2) 0.25134(13) 0.0228(3) Uani 1 1 d . . . . .
O7 O 0.3104(2) 0.3486(2) 0.19674(11) 0.0368(3) Uani 1 1 d . . . . .
N9 N 0.8536(2) 0.5635(2) 0.23695(11) 0.0271(3) Uani 1 1 d . . . . .
O10 O 0.9169(2) 0.5138(2) 0.15840(11) 0.0409(3) Uani 1 1 d . . . . .
O11 O 0.96030(19) 0.5774(2) 0.34103(10) 0.0320(3) Uani 1 1 d . . . . .
N12 N 0.8686(2) 0.6350(2) 0.41799(12) 0.0296(3) Uani 1 1 d . . . . .
C13 C 0.7196(2) 0.6566(2) 0.36531(13) 0.0236(3) Uani 1 1 d . . . . .
C14 C 0.5876(3) 0.7107(2) 0.42614(13) 0.0236(3) Uani 1 1 d . . . . .
N15 N 0.4107(2) 0.6880(3) 0.37878(12) 0.0341(4) Uani 1 1 d . . . . .
O16 O 0.33413(19) 0.7520(2) 0.46509(10) 0.0345(3) Uani 1 1 d . . . . .
C17 C 0.4762(3) 0.8033(2) 0.55442(13) 0.0244(3) Uani 1 1 d . . . . .
N18 N 0.6392(2) 0.7815(2) 0.53452(11) 0.0256(3) Uani 1 1 d . . . . .
N19 N 0.4054(2) 0.8506(2) 0.64245(12) 0.0308(3) Uani 1 1 d . . . . .
N20 N 0.5469(2) 0.9442(2) 0.73172(12) 0.0300(3) Uani 1 1 d . . . . .
O21 O 0.7376(2) 1.0117(2) 0.73374(11) 0.0364(3) Uani 1 1 d . . . . .
O22 O 0.4705(3) 0.9642(3) 0.81418(12) 0.0504(4) Uani 1 1 d . . . . .
K23 K 0.82521(6) 1.18283(6) 0.97684(3) 0.03596(15) Uani 1 1 d . . . . .
K24 K 0.01433(6) 0.20022(7) 0.32284(3) 0.03724(15) 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 1.2652(19) . ?
O2 N3 1.2351(18) . ?
N3 C4 1.375(2) . ?
N5 C4 1.385(2) . ?
N5 O6 1.2353(19) . ?
N5 O7 1.2436(19) . ?
C4 C8 1.444(2) . ?
C8 N9 1.325(2) . ?
C8 C13 1.423(2) . ?
N9 O10 1.2271(19) . ?
N9 O11 1.4311(19) . ?
O11 N12 1.3732(19) . ?
N12 C13 1.308(2) . ?
C13 C14 1.458(2) . ?
C14 N15 1.298(2) . ?
C14 N18 1.367(2) . ?
N15 O16 1.4111(18) . ?
O16 C17 1.349(2) . ?
C17 N18 1.317(2) . ?
C17 N19 1.350(2) . ?
N19 N20 1.337(2) . ?
N20 O21 1.233(2) . ?
N20 O22 1.249(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
O1 N3 C4 116.18(14) . . ?
O2 N3 O1 120.65(14) . . ?
O2 N3 C4 123.17(14) . . ?
O6 N5 C4 122.40(14) . . ?
O6 N5 O7 121.70(14) . . ?
O7 N5 C4 115.90(14) . . ?
N3 C4 N5 122.54(14) . . ?
N3 C4 C8 119.04(14) . . ?
N5 C4 C8 118.36(14) . . ?
N9 C8 C4 121.96(14) . . ?
N9 C8 C13 105.29(14) . . ?
C13 C8 C4 132.73(14) . . ?
C8 N9 O11 108.07(13) . . ?
O10 N9 C8 135.34(15) . . ?
O10 N9 O11 116.56(13) . . ?
N12 O11 N9 108.10(11) . . ?
C13 N12 O11 106.20(13) . . ?
C8 C13 C14 128.61(15) . . ?
N12 C13 C8 112.32(14) . . ?
N12 C13 C14 119.04(15) . . ?
N15 C14 C13 120.49(15) . . ?
N15 C14 N18 116.99(14) . . ?
N18 C14 C13 122.50(14) . . ?
C14 N15 O16 101.99(13) . . ?
C17 O16 N15 107.08(12) . . ?
O16 C17 N19 110.54(14) . . ?
N18 C17 O16 112.54(14) . . ?
N18 C17 N19 136.72(16) . . ?
C17 N18 C14 101.39(14) . . ?
N20 N19 C17 116.38(14) . . ?
O21 N20 N19 123.95(15) . . ?
O21 N20 O22 121.84(16) . . ?
O22 N20 N19 114.17(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
O1 N3 C4 N5 179.02(14) . . . . ?
O1 N3 C4 C8 -3.8(2) . . . . ?
O2 N3 C4 N5 -1.4(2) . . . . ?
O2 N3 C4 C8 175.71(14) . . . . ?
N3 C4 C8 N9 -68.8(2) . . . . ?
N3 C4 C8 C13 109.5(2) . . . . ?
N5 C4 C8 N9 108.49(18) . . . . ?
N5 C4 C8 C13 -73.3(2) . . . . ?
C4 C8 N9 O10 -0.8(3) . . . . ?
C4 C8 N9 O11 177.12(14) . . . . ?
C4 C8 C13 N12 -177.20(17) . . . . ?
C4 C8 C13 C14 4.9(3) . . . . ?
O6 N5 C4 N3 -4.8(2) . . . . ?
O6 N5 C4 C8 178.00(14) . . . . ?
C8 N9 O11 N12 1.41(18) . . . . ?
C8 C13 C14 N15 14.1(3) . . . . ?
C8 C13 C14 N18 -167.75(16) . . . . ?
O7 N5 C4 N3 174.85(14) . . . . ?
O7 N5 C4 C8 -2.3(2) . . . . ?
N9 C8 C13 N12 1.3(2) . . . . ?
N9 C8 C13 C14 -176.67(16) . . . . ?
N9 O11 N12 C13 -0.59(18) . . . . ?
O10 N9 O11 N12 179.81(15) . . . . ?
O11 N12 C13 C8 -0.39(19) . . . . ?
O11 N12 C13 C14 177.77(14) . . . . ?
N12 C13 C14 N15 -163.75(17) . . . . ?
N12 C13 C14 N18 14.4(2) . . . . ?
C13 C8 N9 O10 -179.52(19) . . . . ?
C13 C8 N9 O11 -1.56(17) . . . . ?
C13 C14 N15 O16 178.67(15) . . . . ?
C13 C14 N18 C17 -178.13(16) . . . . ?
C14 N15 O16 C17 -0.73(19) . . . . ?
N15 C14 N18 C17 0.1(2) . . . . ?
N15 O16 C17 N18 0.9(2) . . . . ?
N15 O16 C17 N19 -174.87(14) . . . . ?
O16 C17 N18 C14 -0.60(19) . . . . ?
O16 C17 N19 N20 -166.15(15) . . . . ?
C17 N19 N20 O21 10.1(3) . . . . ?
C17 N19 N20 O22 -172.06(16) . . . . ?
N18 C14 N15 O16 0.4(2) . . . . ?
N18 C17 N19 N20 19.6(3) . . . . ?
N19 C17 N18 C14 173.6(2) . . . . ?

# end Validation Reply Form
# start Validation Reply Form
_vrf_PLAT015_shrv691             
;
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_shrv667
_database_code_depnum_ccdc_archive 'CCDC 1860917'
_audit_update_record             
;
2018-08-07 deposited with the CCDC.
2018-10-30 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         'C5 N10 O5, 2(H4 N)'
_chemical_formula_sum            'C5 H8 N12 O5'
_chemical_formula_weight         316.23

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                   7.1220(7)
_cell_length_b                   7.5186(9)
_cell_length_c                   12.6185(17)
_cell_angle_alpha                76.121(6)
_cell_angle_beta                 74.829(6)
_cell_angle_gamma                67.346(5)
_cell_volume                     594.44(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1427
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      25.09

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.155
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6808
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_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            7147
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_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         2.972
_diffrn_reflns_theta_max         29.967
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3264
_reflns_number_gt                2035
_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)+(0.0479P)²+0.1110P] 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         3264
_refine_ls_number_parameters     223
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      0.999
_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 0.9204(3) 0.3498(2) 0.48824(14) 0.0521(4) Uani 1 1 d . . . . .
O2 O 0.7835(3) 0.1513(2) 0.46984(18) 0.0724(6) Uani 1 1 d . . . . .
N3 N 0.7944(3) 0.3141(2) 0.45261(13) 0.0329(4) Uani 1 1 d . . . . .
N4 N 0.6714(2) 0.4692(2) 0.39519(12) 0.0267(3) Uani 1 1 d . . . . .
C5 C 0.5354(3) 0.4381(2) 0.35133(14) 0.0221(4) Uani 1 1 d . . . . .
O6 O 0.4253(2) 0.60557(17) 0.29456(12) 0.0355(4) Uani 1 1 d . . . . .
N7 N 0.2910(3) 0.5612(2) 0.24891(14) 0.0355(4) Uani 1 1 d . . . . .
C9 C 0.3356(3) 0.3750(2) 0.28354(14) 0.0240(4) Uani 1 1 d . . . . .
N10 N 0.4845(2) 0.2891(2) 0.34770(12) 0.0265(3) Uani 1 1 d . . . . .
C11 C 0.2383(3) 0.2571(2) 0.25486(15) 0.0260(4) Uani 1 1 d . . . . .
N12 N 0.3222(3) 0.0686(2) 0.28264(16) 0.0437(5) Uani 1 1 d . . . . .
O13 O 0.2116(3) -0.01597(18) 0.25073(14) 0.0497(4) Uani 1 1 d . . . . .
N14 N 0.0528(3) 0.1354(2) 0.19981(13) 0.0300(4) Uani 1 1 d . . . . .
O15 O -0.0607(2) 0.08148(18) 0.16563(12) 0.0391(4) Uani 1 1 d . . . . .
C16 C 0.0686(3) 0.3054(2) 0.20092(14) 0.0218(4) Uani 1 1 d . . . . .
C17 C -0.0720(3) 0.4845(2) 0.14913(13) 0.0201(3) Uani 1 1 d . . . . .
N18 N -0.2107(2) 0.4860(2) 0.09464(12) 0.0261(3) Uani 1 1 d . . . . .
N19 N -0.3007(2) 0.6754(2) 0.05680(13) 0.0292(4) Uani 1 1 d . . . . .
N20 N -0.2199(2) 0.7807(2) 0.08765(13) 0.0300(4) Uani 1 1 d . . . . .
N21 N -0.0732(3) 0.6634(2) 0.14644(13) 0.0286(4) Uani 1 1 d . . . . .
N22 N 0.2345(3) 0.1647(2) 0.62309(16) 0.0395(4) Uani 1 1 d D . . . .
H22A H 0.299(3) 0.254(2) 0.6031(16) 0.059 Uiso 1 1 d D U . . .
H22B H 0.147(3) 0.188(3) 0.5759(16) 0.059 Uiso 1 1 d D U . . .
H22C H 0.326(3) 0.0424(17) 0.6190(18) 0.059 Uiso 1 1 d D U . . .
H22D H 0.165(3) 0.173(3) 0.6946(10) 0.059 Uiso 1 1 d D U . . .
N23 N 0.7125(3) 0.2036(2) 0.99191(14) 0.0297(4) Uani 1 1 d D . . . .
H23A H 0.798(3) 0.217(3) 0.9250(10) 0.044 Uiso 1 1 d D U . . .
H23B H 0.5784(16) 0.248(3) 0.9819(17) 0.044 Uiso 1 1 d D U . . .
H23C H 0.742(3) 0.0758(15) 1.0231(14) 0.044 Uiso 1 1 d D U . . .
H23D H 0.730(3) 0.273(2) 1.0366(13) 0.044 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 1.2388(19) . ?
O2 N3 1.219(2) . ?
N3 N4 1.339(2) . ?
N4 C5 1.348(2) . ?
C5 N10 1.317(2) . ?
C5 O6 1.3468(19) . ?
O6 N7 1.4084(19) . ?
N7 C9 1.300(2) . ?
C9 N10 1.367(2) . ?
C9 C11 1.467(2) . ?
C11 N12 1.307(2) . ?
C11 C16 1.425(2) . ?
N12 O13 1.365(2) . ?
O13 N14 1.423(2) . ?
N14 O15 1.2339(18) . ?
N14 C16 1.329(2) . ?
C16 C17 1.458(2) . ?
C17 N21 1.334(2) . ?
C17 N18 1.339(2) . ?
N18 N19 1.341(2) . ?
N19 N20 1.314(2) . ?
N20 N21 1.342(2) . ?
N22 H22A 0.909(9) . ?
N22 H22B 0.911(9) . ?
N22 H22C 0.904(9) . ?
N22 H22D 0.913(9) . ?
N23 H23A 0.911(9) . ?
N23 H23B 0.915(9) . ?
N23 H23C 0.910(9) . ?
N23 H23D 0.914(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 122.29(17) . . ?
O2 N3 N4 123.49(15) . . ?
O1 N3 N4 114.22(15) . . ?
N3 N4 C5 116.92(14) . . ?
N10 C5 O6 112.37(14) . . ?
N10 C5 N4 137.28(16) . . ?
O6 C5 N4 110.34(13) . . ?
C5 O6 N7 107.19(12) . . ?
C9 N7 O6 102.25(13) . . ?
N7 C9 N10 116.49(15) . . ?
N7 C9 C11 123.31(15) . . ?
N10 C9 C11 120.18(14) . . ?
C5 N10 C9 101.71(13) . . ?
N12 C11 C16 111.65(15) . . ?
N12 C11 C9 115.24(15) . . ?
C16 C11 C9 133.11(15) . . ?
C11 N12 O13 107.00(15) . . ?
N12 O13 N14 107.91(12) . . ?
O15 N14 C16 136.01(16) . . ?
O15 N14 O13 115.66(13) . . ?
C16 N14 O13 108.33(14) . . ?
N14 C16 C11 105.09(14) . . ?
N14 C16 C17 119.23(15) . . ?
C11 C16 C17 135.65(14) . . ?
N21 C17 N18 112.26(14) . . ?
N21 C17 C16 124.72(15) . . ?
N18 C17 C16 122.98(14) . . ?
C17 N18 N19 104.07(13) . . ?
N20 N19 N18 109.83(13) . . ?
N19 N20 N21 109.62(13) . . ?
C17 N21 N20 104.23(14) . . ?
H22A N22 H22B 110.2(16) . . ?
H22A N22 H22C 111.6(17) . . ?
H22B N22 H22C 106(2) . . ?
H22A N22 H22D 107.6(16) . . ?
H22B N22 H22D 112(2) . . ?
H22C N22 H22D 109.4(16) . . ?
H23A N23 H23B 109.6(15) . . ?
H23A N23 H23C 111.0(15) . . ?
H23B N23 H23C 106.4(18) . . ?
H23A N23 H23D 107.6(15) . . ?
H23B N23 H23D 111.6(18) . . ?
H23C N23 H23D 110.7(15) . . ?

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 N4 C5 -2.7(3) . . . . ?
O1 N3 N4 C5 177.97(17) . . . . ?
N3 N4 C5 N10 -0.3(3) . . . . ?
N3 N4 C5 O6 -178.92(15) . . . . ?
N10 C5 O6 N7 -0.5(2) . . . . ?
N4 C5 O6 N7 178.50(15) . . . . ?
C5 O6 N7 C9 0.2(2) . . . . ?
O6 N7 C9 N10 0.2(2) . . . . ?
O6 N7 C9 C11 -178.35(17) . . . . ?
O6 C5 N10 C9 0.5(2) . . . . ?
N4 C5 N10 C9 -178.0(2) . . . . ?
N7 C9 N10 C5 -0.4(2) . . . . ?
C11 C9 N10 C5 178.13(17) . . . . ?
N7 C9 C11 N12 170.26(19) . . . . ?
N10 C9 C11 N12 -8.2(3) . . . . ?
N7 C9 C11 C16 -9.1(3) . . . . ?
N10 C9 C11 C16 172.46(19) . . . . ?
C16 C11 N12 O13 -1.0(2) . . . . ?
C9 C11 N12 O13 179.48(17) . . . . ?
C11 N12 O13 N14 0.5(2) . . . . ?
N12 O13 N14 O15 179.59(17) . . . . ?
N12 O13 N14 C16 0.2(2) . . . . ?
O15 N14 C16 C11 -180.0(2) . . . . ?
O13 N14 C16 C11 -0.8(2) . . . . ?
O15 N14 C16 C17 -1.7(3) . . . . ?
O13 N14 C16 C17 177.48(16) . . . . ?
N12 C11 C16 N14 1.2(2) . . . . ?
C9 C11 C16 N14 -179.5(2) . . . . ?
N12 C11 C16 C17 -176.7(2) . . . . ?
C9 C11 C16 C17 2.7(4) . . . . ?
N14 C16 C17 N21 178.95(18) . . . . ?
C11 C16 C17 N21 -3.4(3) . . . . ?
N14 C16 C17 N18 -3.7(3) . . . . ?
C11 C16 C17 N18 173.9(2) . . . . ?
N21 C17 N18 N19 0.1(2) . . . . ?
C16 C17 N18 N19 -177.59(16) . . . . ?
C17 N18 N19 N20 -0.20(19) . . . . ?
N18 N19 N20 N21 0.3(2) . . . . ?
N18 C17 N21 N20 0.1(2) . . . . ?
C16 C17 N21 N20 177.70(16) . . . . ?
N19 N20 N21 C17 -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
N22 H22A N4 0.909(9) 2.173(12) 3.019(2) 154.4(18) 2_666
N22 H22B O1 0.911(9) 2.023(13) 2.880(2) 156(2) 1_455
N22 H22C N10 0.904(9) 2.326(11) 3.210(2) 165.7(19) 2_656
N22 H22D O15 0.913(9) 2.469(17) 3.121(2) 128.5(16) 2_556
N22 H22D N21 0.913(9) 2.419(15) 3.218(3) 146.2(18) 2_566
N23 H23A N7 0.911(9) 2.481(16) 3.129(2) 128.3(15) 2_666
N23 H23A O15 0.911(9) 2.591(16) 3.172(2) 122.2(14) 2_656
N23 H23A N21 0.911(9) 2.348(14) 3.072(2) 136.3(15) 2_666
N23 H23B N19 0.915(9) 1.994(10) 2.903(2) 172.3(19) 2_566
N23 H23C N20 0.910(9) 2.109(9) 3.014(2) 173.1(19) 1_646
N23 H23D O15 0.914(9) 2.331(19) 2.829(2) 114.0(14) 1_656
N23 H23D N18 0.914(9) 2.126(10) 3.012(2) 163.0(16) 1_656

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.051

# start Validation Reply Form
_vrf_PLAT015_shrv667             
;
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_PLAT430_shrv667             
;
PROBLEM: Short Inter D...A Contact  O6       ..O13              2.66 Ang.  
RESPONSE: High-density energetic materials often display close contacts.
;
# 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_shrv660
_database_code_depnum_ccdc_archive 'CCDC 1860916'
_audit_update_record             
;
2018-08-07 deposited with the CCDC.
2018-10-30 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         'C4 N8 O6, 2(H4 N)'
_chemical_formula_sum            'C4 H8 N10 O6'
_chemical_formula_weight         292.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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      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                   7.4560(3)
_cell_length_b                   8.5912(3)
_cell_length_c                   9.9008(4)
_cell_angle_alpha                73.599(2)
_cell_angle_beta                 83.431(2)
_cell_angle_gamma                65.465(2)
_cell_volume                     553.46(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3043
_cell_measurement_theta_min      4.656
_cell_measurement_theta_max      74.415

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_F_000             300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.091
_exptl_absorpt_coefficient_mu    1.416
_shelx_estimated_absorpt_T_min   0.776
_shelx_estimated_absorpt_T_max   0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6533
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(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            3309
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.656
_diffrn_reflns_theta_max         74.406
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.792
_diffrn_measured_fraction_theta_full 0.832
_diffrn_reflns_Laue_measured_fraction_max 0.792
_diffrn_reflns_Laue_measured_fraction_full 0.832
_diffrn_reflns_point_group_measured_fraction_max 0.792
_diffrn_reflns_point_group_measured_fraction_full 0.832
_reflns_number_total             1795
_reflns_number_gt                1660
_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)+(0.0552P)²+0.4689P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.026(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1795
_refine_ls_number_parameters     206
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.1015
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.108
_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 0.8252(2) 0.81438(19) 0.67366(16) 0.0214(4) Uani 1 1 d . . . . .
O2 O 0.8112(2) 0.7286(2) 0.49114(16) 0.0252(4) Uani 1 1 d . . . . .
N3 N 0.7325(2) 0.7830(2) 0.59458(18) 0.0171(4) Uani 1 1 d . . . . .
C4 C 0.5365(3) 0.8129(3) 0.6346(2) 0.0164(4) Uani 1 1 d . . . . .
N5 N 0.4106(2) 0.7988(2) 0.55224(18) 0.0175(4) Uani 1 1 d . . . . .
O6 O 0.4594(2) 0.7609(2) 0.43689(16) 0.0260(4) Uani 1 1 d . . . . .
O7 O 0.2374(2) 0.82781(19) 0.59803(16) 0.0204(4) Uani 1 1 d . . . . .
C8 C 0.4803(3) 0.8418(3) 0.7748(2) 0.0149(4) Uani 1 1 d . . . . .
N9 N 0.3400(2) 0.9878(2) 0.79541(18) 0.0177(4) Uani 1 1 d . . . . .
O10 O 0.3264(2) 0.96941(18) 0.93804(15) 0.0187(4) Uani 1 1 d . . . . .
N11 N 0.4740(2) 0.7977(2) 1.00531(18) 0.0159(4) Uani 1 1 d . . . . .
O12 O 0.4829(2) 0.75889(19) 1.13432(15) 0.0223(4) Uani 1 1 d . . . . .
C13 C 0.5677(3) 0.7208(2) 0.9049(2) 0.0145(4) Uani 1 1 d . . . . .
C14 C 0.7198(3) 0.5420(2) 0.9334(2) 0.0147(4) Uani 1 1 d . . . . .
N15 N 0.7862(2) 0.4384(2) 1.06195(18) 0.0185(4) Uani 1 1 d . . . . .
N16 N 0.9184(2) 0.2851(2) 1.03774(19) 0.0186(4) Uani 1 1 d . . . . .
N17 N 0.9281(2) 0.2983(2) 0.90186(19) 0.0189(4) Uani 1 1 d . . . . .
N18 N 0.8039(3) 0.4611(2) 0.83172(19) 0.0191(4) Uani 1 1 d . . . . .
N19 N 0.9212(2) 0.0604(2) 0.74412(19) 0.0174(4) Uani 1 1 d D . . . .
H19A H 0.935(3) 0.134(2) 0.787(2) 0.026 Uiso 1 1 d D U . . .
H19B H 1.002(3) 0.042(3) 0.6703(17) 0.026 Uiso 1 1 d D U . . .
H19C H 0.797(2) 0.103(3) 0.711(2) 0.026 Uiso 1 1 d D U . . .
H19D H 0.947(3) -0.0459(17) 0.8086(18) 0.026 Uiso 1 1 d D U . . .
N20 N 0.8106(3) 0.5134(2) 0.32250(19) 0.0198(4) Uani 1 1 d D . . . .
H20A H 0.717(3) 0.600(2) 0.358(2) 0.030 Uiso 1 1 d D U . . .
H20B H 0.774(4) 0.511(3) 0.2399(15) 0.030 Uiso 1 1 d D U . . .
H20C H 0.920(2) 0.536(3) 0.304(3) 0.030 Uiso 1 1 d D U . . .
H20D H 0.840(3) 0.4066(18) 0.3868(19) 0.030 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 1.249(2) . ?
O2 N3 1.232(2) . ?
N3 C4 1.405(3) . ?
C4 N5 1.373(2) . ?
C4 C8 1.463(3) . ?
N5 O6 1.249(2) . ?
N5 O7 1.264(2) . ?
C8 N9 1.310(3) . ?
C8 C13 1.427(3) . ?
N9 O10 1.373(2) . ?
O10 N11 1.448(2) . ?
N11 O12 1.228(2) . ?
N11 C13 1.319(3) . ?
C13 C14 1.452(3) . ?
C14 N18 1.334(3) . ?
C14 N15 1.340(3) . ?
N15 N16 1.345(2) . ?
N16 N17 1.314(2) . ?
N17 N18 1.349(2) . ?
N19 H19A 0.903(9) . ?
N19 H19B 0.900(9) . ?
N19 H19C 0.905(9) . ?
N19 H19D 0.912(9) . ?
N20 H20A 0.906(9) . ?
N20 H20B 0.900(9) . ?
N20 H20C 0.902(9) . ?
N20 H20D 0.911(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 121.38(17) . . ?
O2 N3 C4 123.88(16) . . ?
O1 N3 C4 114.74(17) . . ?
N5 C4 N3 121.70(18) . . ?
N5 C4 C8 121.83(18) . . ?
N3 C4 C8 116.18(16) . . ?
O6 N5 O7 120.06(16) . . ?
O6 N5 C4 123.26(17) . . ?
O7 N5 C4 116.69(17) . . ?
N9 C8 C13 111.13(18) . . ?
N9 C8 C4 122.76(17) . . ?
C13 C8 C4 126.11(17) . . ?
C8 N9 O10 107.21(15) . . ?
N9 O10 N11 107.69(13) . . ?
O12 N11 C13 136.17(17) . . ?
O12 N11 O10 116.51(15) . . ?
C13 N11 O10 107.33(15) . . ?
N11 C13 C8 106.64(16) . . ?
N11 C13 C14 122.92(18) . . ?
C8 C13 C14 130.32(18) . . ?
N18 C14 N15 112.66(17) . . ?
N18 C14 C13 122.42(18) . . ?
N15 C14 C13 124.88(18) . . ?
C14 N15 N16 104.06(16) . . ?
N17 N16 N15 109.51(16) . . ?
N16 N17 N18 110.05(16) . . ?
C14 N18 N17 103.73(16) . . ?
H19A N19 H19B 113.9(18) . . ?
H19A N19 H19C 111.4(17) . . ?
H19B N19 H19C 107(2) . . ?
H19A N19 H19D 108.0(16) . . ?
H19B N19 H19D 108.4(16) . . ?
H19C N19 H19D 108.4(16) . . ?
H20A N20 H20B 112.1(17) . . ?
H20A N20 H20C 108.9(17) . . ?
H20B N20 H20C 106(2) . . ?
H20A N20 H20D 109.6(17) . . ?
H20B N20 H20D 110.9(17) . . ?
H20C N20 H20D 109.6(17) . . ?

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 N5 -6.3(3) . . . . ?
O1 N3 C4 N5 174.46(17) . . . . ?
O2 N3 C4 C8 167.72(18) . . . . ?
O1 N3 C4 C8 -11.5(2) . . . . ?
N3 C4 N5 O6 -0.7(3) . . . . ?
C8 C4 N5 O6 -174.39(17) . . . . ?
N3 C4 N5 O7 179.79(16) . . . . ?
C8 C4 N5 O7 6.1(3) . . . . ?
N5 C4 C8 N9 -66.1(3) . . . . ?
N3 C4 C8 N9 119.9(2) . . . . ?
N5 C4 C8 C13 114.5(2) . . . . ?
N3 C4 C8 C13 -59.5(3) . . . . ?
C13 C8 N9 O10 -0.8(2) . . . . ?
C4 C8 N9 O10 179.71(16) . . . . ?
C8 N9 O10 N11 0.61(19) . . . . ?
N9 O10 N11 O12 179.92(15) . . . . ?
N9 O10 N11 C13 -0.18(19) . . . . ?
O12 N11 C13 C8 179.6(2) . . . . ?
O10 N11 C13 C8 -0.29(19) . . . . ?
O12 N11 C13 C14 3.2(3) . . . . ?
O10 N11 C13 C14 -176.71(17) . . . . ?
N9 C8 C13 N11 0.7(2) . . . . ?
C4 C8 C13 N11 -179.84(17) . . . . ?
N9 C8 C13 C14 176.77(19) . . . . ?
C4 C8 C13 C14 -3.8(3) . . . . ?
N11 C13 C14 N18 175.18(17) . . . . ?
C8 C13 C14 N18 -0.3(3) . . . . ?
N11 C13 C14 N15 -2.3(3) . . . . ?
C8 C13 C14 N15 -177.79(19) . . . . ?
N18 C14 N15 N16 0.0(2) . . . . ?
C13 C14 N15 N16 177.65(18) . . . . ?
C14 N15 N16 N17 -0.3(2) . . . . ?
N15 N16 N17 N18 0.5(2) . . . . ?
N15 C14 N18 N17 0.3(2) . . . . ?
C13 C14 N18 N17 -177.43(18) . . . . ?
N16 N17 N18 C14 -0.5(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
N19 H19A N17 0.903(9) 2.026(10) 2.920(2) 171(2) .
N19 H19B O7 0.900(9) 2.178(16) 2.930(2) 140.7(19) 1_645
N19 H19C O6 0.905(9) 2.233(11) 3.100(2) 160(2) 2_666
N19 H19C O12 0.905(9) 2.52(2) 3.046(2) 117.8(18) 2_667
N19 H19D N16 0.912(9) 2.102(11) 2.988(2) 163.6(19) 2_757
N20 H20A O2 0.906(9) 2.27(2) 2.821(2) 119.0(17) .
N20 H20A O6 0.906(9) 2.068(11) 2.953(2) 165(2) .
N20 H20B O12 0.900(9) 2.40(2) 2.904(2) 115.7(17) 1_554
N20 H20B N15 0.900(9) 2.010(12) 2.872(2) 160(2) 1_554
N20 H20C N17 0.902(9) 2.574(17) 3.309(3) 139(2) 2_766
N20 H20C N18 0.902(9) 2.332(14) 3.158(3) 152(2) 2_766
N20 H20D O2 0.911(9) 2.64(2) 3.136(2) 114.7(16) 2_766
N20 H20D O7 0.911(9) 2.277(18) 2.974(2) 133.0(18) 2_666

_refine_diff_density_max         0.426
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.062

# start Validation Reply Form
_vrf_PLAT015_shrv660             
;
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_shrv660             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.832 Why?  
RESPONSE: Low data completeness is often encountered in triclinic unit 
cells when utilizing Cu radiation.
;
_vrf_PLAT911_shrv660             
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        337 Report
RESPONSE: Low data completeness is often encountered in triclinic unit 
cells when utilizing Cu radiation.
;
# end Validation Reply Form
