# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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. 
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data_js118a
_database_code_depnum_ccdc_archive 'CCDC 1884589'
_audit_update_record             
;
2018-12-11 deposited with the CCDC.
2019-02-07 downloaded from the CCDC.
;
_audit_creation_date             2018-01-09
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.12.08 svn.r3473 for OlexSys, GUI svn.r5433)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H3 N9 O4, 2(H4 N), 2(H2 O)'
_chemical_formula_sum            'C5 H15 N11 O6'
_chemical_formula_weight         325.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   7.5623(11)
_cell_length_b                   10.2596(15)
_cell_length_c                   19.026(3)
_cell_angle_alpha                97.880(2)
_cell_angle_beta                 91.529(2)
_cell_angle_gamma                109.537(2)
_cell_volume                     1373.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7659
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.28
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0702 before and 0.0552 after correction. The Ratio of minimum to maximum transmission is 0.8920. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.227
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.101
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18302
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_min         1.084
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3847
_reflns_number_total             4997
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     485
_refine_ls_number_reflns         4997
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0681
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1287P)²+3.2224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2307
_refine_ls_wR_factor_ref         0.2425
_refine_special_details          
'The structure was refined by Least Squares using version 2014/6 of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). All non-hydrogen atoms were refined anisotropically. Hydrogen atom positions were calculated geometrically and refined using the riding model, except for the Hydrogen atom on the nitrogen atom which was found by difference Fourier methods and refined isotropically.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 N3C-H3CC \\sim N3C-H3CA \\sim N3C-H3CB \\sim N3C-H3CD
 with sigma of 0.02
 N2C-H2CB \\sim N2C-H2CA \\sim N2C-H2CD \\sim N2C-H2CC
 with sigma of 0.02
 N4C-H4CB \\sim N4C-H4CA \\sim N4C-H4CD \\sim N4C-H4CC
 with sigma of 0.02
 N1C-H1CB \\sim N1C-H1CD \\sim N1C-H1CA \\sim N1C-H1CC
 with sigma of 0.02
3.a Free rotating group:
 O1S(H1SA,H1SB), O3S(H3SA,H3SB)
3.b Idealised Me refined as rotating group:
 C5A(H5AA,H5AB,H5AC), C5B(H5BA,H5BB,H5BC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.3227(4) 0.4397(3) 0.11851(16) 0.0354(7) Uani 1 1 d . . . . .
O2A O 0.5109(5) 0.5174(4) 0.21476(18) 0.0460(9) Uani 1 1 d . . . . .
O3A O 0.4852(4) 0.7327(4) 0.29222(16) 0.0423(8) Uani 1 1 d . . . . .
O4A O 0.2897(4) 0.8240(3) 0.25151(18) 0.0425(8) Uani 1 1 d . . . . .
N1A N 0.4049(5) 0.7985(4) -0.03276(19) 0.0346(8) Uani 1 1 d . . . . .
N2A N 0.5868(6) 0.8677(4) -0.0385(2) 0.0384(9) Uani 1 1 d . . . . .
N3A N 0.6802(5) 0.8934(4) 0.0237(2) 0.0393(9) Uani 1 1 d . . . . .
N4A N 0.5613(5) 0.8422(4) 0.0727(2) 0.0334(8) Uani 1 1 d . . . . .
N5A N 0.0511(5) 0.6864(4) 0.03181(18) 0.0291(8) Uani 1 1 d . . . . .
N6A N -0.0695(5) 0.6149(4) 0.07361(19) 0.0291(8) Uani 1 1 d . . . . .
N7A N 0.0037(5) 0.5899(4) 0.13218(17) 0.0279(8) Uani 1 1 d . . . . .
N8A N 0.3894(5) 0.5303(4) 0.17276(18) 0.0291(8) Uani 1 1 d . . . . .
N9A N 0.3713(5) 0.7349(4) 0.24448(18) 0.0306(8) Uani 1 1 d . . . . .
C1A C 0.3932(6) 0.7848(4) 0.0358(2) 0.0262(8) Uani 1 1 d . . . . .
C2A C 0.2200(6) 0.7110(4) 0.0665(2) 0.0265(9) Uani 1 1 d . . . . .
C3A C 0.1897(5) 0.6507(4) 0.1283(2) 0.0264(9) Uani 1 1 d . . . . .
C4A C 0.3253(5) 0.6414(4) 0.1823(2) 0.0263(9) Uani 1 1 d . . . . .
C5A C -0.2722(6) 0.5712(5) 0.0579(3) 0.0357(10) Uani 1 1 d . . . . .
H5AA H -0.3212 0.6372 0.0861 0.054 Uiso 1 1 calc GR . . . .
H5AB H -0.3321 0.4773 0.0700 0.054 Uiso 1 1 calc GR . . . .
H5AC H -0.2999 0.5699 0.0072 0.054 Uiso 1 1 calc GR . . . .
O1B O 0.3659(4) 0.1234(3) 0.43661(16) 0.0332(7) Uani 1 1 d . . . . .
O2B O 0.1253(4) -0.0678(3) 0.41130(16) 0.0341(7) Uani 1 1 d . . . . .
O3B O -0.2027(4) 0.1700(3) 0.44267(16) 0.0322(7) Uani 1 1 d . . . . .
O4B O -0.1945(4) -0.0325(3) 0.39555(18) 0.0359(7) Uani 1 1 d . . . . .
N1B N 0.0948(5) 0.5462(4) 0.36820(19) 0.0324(8) Uani 1 1 d . . . . .
N2B N 0.0221(5) 0.5167(4) 0.30013(19) 0.0330(8) Uani 1 1 d . . . . .
N3B N -0.0155(5) 0.3835(4) 0.27699(19) 0.0332(8) Uani 1 1 d . . . . .
N4B N 0.0341(6) 0.3219(4) 0.32836(19) 0.0345(8) Uani 1 1 d . . . . .
N5B N 0.2666(5) 0.5202(4) 0.50126(18) 0.0272(7) Uani 1 1 d . . . . .
N6B N 0.3115(5) 0.4637(4) 0.55452(18) 0.0265(7) Uani 1 1 d . . . . .
N7B N 0.2521(5) 0.3253(3) 0.54558(17) 0.0266(7) Uani 1 1 d . . . . .
N8B N 0.1895(4) 0.0614(3) 0.43029(17) 0.0254(7) Uani 1 1 d . . . . .
N9B N -0.1134(4) 0.0875(3) 0.42783(17) 0.0244(7) Uani 1 1 d . . . . .
C1B C 0.0990(5) 0.4252(4) 0.3836(2) 0.0255(8) Uani 1 1 d . . . . .
C2B C 0.1723(5) 0.4090(4) 0.4526(2) 0.0235(8) Uani 1 1 d . . . . .
C3B C 0.1632(5) 0.2874(4) 0.47979(19) 0.0231(8) Uani 1 1 d . . . . .
C4B C 0.0781(5) 0.1411(4) 0.4464(2) 0.0242(8) Uani 1 1 d . . . . .
C5B C 0.4074(6) 0.5489(5) 0.6214(2) 0.0317(9) Uani 1 1 d . . . . .
H5BA H 0.3143 0.5663 0.6528 0.048 Uiso 1 1 calc GR . . . .
H5BB H 0.4952 0.6383 0.6119 0.048 Uiso 1 1 calc GR . . . .
H5BC H 0.4770 0.4992 0.6446 0.048 Uiso 1 1 calc GR . . . .
N4C N -0.1114(6) 0.7548(4) 0.2919(2) 0.0360(9) Uani 1 1 d D . . . .
H4CA H -0.045(9) 0.827(6) 0.265(3) 0.08(2) Uiso 1 1 d D . . . .
H4CB H -0.073(8) 0.675(4) 0.277(3) 0.056(16) Uiso 1 1 d D . . . .
H4CC H -0.239(6) 0.729(7) 0.272(4) 0.08(2) Uiso 1 1 d D . . . .
H4CD H -0.145(13) 0.783(9) 0.339(3) 0.12(3) Uiso 1 1 d D . . . .
N3C N 0.4015(5) 0.8007(4) 0.43388(19) 0.0274(8) Uani 1 1 d D . . . .
H3CA H 0.328(8) 0.718(4) 0.434(4) 0.07(2) Uiso 1 1 d D . . . .
H3CB H 0.478(7) 0.810(6) 0.469(2) 0.057(17) Uiso 1 1 d D . . . .
H3CC H 0.355(9) 0.865(5) 0.434(4) 0.07(2) Uiso 1 1 d D . . . .
H3CD H 0.454(14) 0.798(11) 0.396(3) 0.15(4) Uiso 1 1 d D . . . .
N2C N -0.0685(6) 0.2590(4) 0.1264(2) 0.0361(9) Uani 1 1 d D . . . .
H2CA H 0.007(7) 0.332(5) 0.109(3) 0.061(18) Uiso 1 1 d D . . . .
H2CB H -0.071(7) 0.293(5) 0.1719(16) 0.044(14) Uiso 1 1 d D . . . .
H2CC H -0.040(8) 0.181(4) 0.120(3) 0.057(17) Uiso 1 1 d D . . . .
H2CD H -0.178(6) 0.243(6) 0.101(3) 0.061(18) Uiso 1 1 d D . . . .
N1C N 0.5781(6) 1.0892(4) 0.3002(2) 0.0380(9) Uani 1 1 d D . . . .
H1CA H 0.652(8) 1.125(6) 0.339(2) 0.07(2) Uiso 1 1 d D . . . .
H1CB H 0.645(7) 1.049(5) 0.273(3) 0.054(17) Uiso 1 1 d D . . . .
H1CC H 0.477(6) 1.022(5) 0.310(3) 0.066(19) Uiso 1 1 d D . . . .
H1CD H 0.562(9) 1.153(5) 0.277(3) 0.062(18) Uiso 1 1 d D . . . .
O1S O 0.1225(6) 1.0757(4) 0.2689(2) 0.0548(10) Uani 1 1 d . . . . .
H1SA H 0.0946 1.1453 0.2912 0.082 Uiso 1 1 d G . . . .
H1SB H 0.2020 1.1129 0.2390 0.082 Uiso 1 1 d G . . . .
O4S O 0.4618(6) 1.2247(5) 0.1966(2) 0.0515(10) Uani 1 1 d . . . . .
H4SA H 0.516(9) 1.325(8) 0.197(3) 0.065(19) Uiso 1 1 d . . . . .
H4SB H 0.441(10) 1.193(7) 0.160(4) 0.07(2) Uiso 1 1 d . . . . .
O2S O 0.0387(6) 1.0163(4) 0.1017(2) 0.0462(9) Uani 1 1 d . . . . .
H2SA H -0.038(10) 0.972(7) 0.070(4) 0.06(2) Uiso 1 1 d . . . . .
H2SB H 0.141(10) 1.025(7) 0.084(4) 0.07(2) Uiso 1 1 d . . . . .
O3S O 0.7481(6) 0.9369(4) 0.20909(19) 0.0550(10) Uani 1 1 d . . . . .
H3SA H 0.8677 0.9788 0.2058 0.083 Uiso 1 1 d G . . . .
H3SB H 0.7011 0.9086 0.1652 0.083 Uiso 1 1 d G . . . .


_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 N8A 1.257(5) . ?
O2A N8A 1.254(5) . ?
O3A N9A 1.243(5) . ?
O4A N9A 1.258(5) . ?
N1A N2A 1.336(5) . ?
N1A C1A 1.334(5) . ?
N2A N3A 1.310(6) . ?
N3A N4A 1.347(5) . ?
N4A C1A 1.339(5) . ?
N5A N6A 1.324(5) . ?
N5A C2A 1.350(5) . ?
N6A N7A 1.324(5) . ?
N6A C5A 1.456(5) . ?
N7A C3A 1.343(5) . ?
N8A C4A 1.372(5) . ?
N9A C4A 1.373(5) . ?
C1A C2A 1.459(6) . ?
C2A C3A 1.393(6) . ?
C3A C4A 1.466(5) . ?
C5A H5AA 0.9800 . ?
C5A H5AB 0.9800 . ?
C5A H5AC 0.9800 . ?
O1B N8B 1.265(4) . ?
O2B N8B 1.246(4) . ?
O3B N9B 1.256(4) . ?
O4B N9B 1.240(4) . ?
N1B N2B 1.347(5) . ?
N1B C1B 1.324(5) . ?
N2B N3B 1.309(5) . ?
N3B N4B 1.343(5) . ?
N4B C1B 1.338(5) . ?
N5B N6B 1.324(5) . ?
N5B C2B 1.341(5) . ?
N6B N7B 1.323(5) . ?
N6B C5B 1.460(5) . ?
N7B C3B 1.348(5) . ?
N8B C4B 1.370(5) . ?
N9B C4B 1.383(5) . ?
C1B C2B 1.463(6) . ?
C2B C3B 1.397(6) . ?
C3B C4B 1.463(6) . ?
C5B H5BA 0.9800 . ?
C5B H5BB 0.9800 . ?
C5B H5BC 0.9800 . ?
N4C H4CA 0.96(3) . ?
N4C H4CB 0.97(3) . ?
N4C H4CC 0.96(3) . ?
N4C H4CD 0.97(3) . ?
N3C H3CA 0.84(3) . ?
N3C H3CB 0.84(3) . ?
N3C H3CC 0.84(3) . ?
N3C H3CD 0.84(3) . ?
N2C H2CA 0.89(3) . ?
N2C H2CB 0.89(3) . ?
N2C H2CC 0.89(3) . ?
N2C H2CD 0.90(3) . ?
N1C H1CA 0.88(3) . ?
N1C H1CB 0.89(3) . ?
N1C H1CC 0.88(3) . ?
N1C H1CD 0.88(3) . ?
O1S H1SA 0.8694 . ?
O1S H1SB 0.8699 . ?
O4S H4SA 0.97(7) . ?
O4S H4SB 0.71(8) . ?
O2S H2SA 0.79(7) . ?
O2S H2SB 0.83(8) . ?
O3S H3SA 0.8699 . ?
O3S H3SB 0.8704 . ?

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
C1A N1A N2A 104.8(4) . . ?
N3A N2A N1A 109.6(3) . . ?
N2A N3A N4A 109.7(4) . . ?
C1A N4A N3A 104.1(4) . . ?
N6A N5A C2A 103.2(3) . . ?
N5A N6A N7A 116.5(3) . . ?
N5A N6A C5A 122.0(3) . . ?
N7A N6A C5A 121.5(3) . . ?
N6A N7A C3A 103.1(3) . . ?
O1A N8A C4A 117.2(3) . . ?
O2A N8A O1A 119.8(3) . . ?
O2A N8A C4A 123.1(4) . . ?
O3A N9A O4A 120.8(3) . . ?
O3A N9A C4A 122.9(4) . . ?
O4A N9A C4A 116.3(3) . . ?
N1A C1A N4A 111.8(4) . . ?
N1A C1A C2A 124.2(4) . . ?
N4A C1A C2A 124.0(4) . . ?
N5A C2A C1A 120.3(4) . . ?
N5A C2A C3A 108.3(4) . . ?
C3A C2A C1A 131.3(4) . . ?
N7A C3A C2A 108.9(3) . . ?
N7A C3A C4A 121.0(4) . . ?
C2A C3A C4A 130.0(4) . . ?
N8A C4A N9A 120.9(4) . . ?
N8A C4A C3A 119.0(3) . . ?
N9A C4A C3A 119.8(4) . . ?
N6A C5A H5AA 109.5 . . ?
N6A C5A H5AB 109.5 . . ?
N6A C5A H5AC 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
C1B N1B N2B 104.6(3) . . ?
N3B N2B N1B 109.3(3) . . ?
N2B N3B N4B 109.8(3) . . ?
C1B N4B N3B 104.1(3) . . ?
N6B N5B C2B 103.5(3) . . ?
N5B N6B C5B 121.8(3) . . ?
N7B N6B N5B 116.1(3) . . ?
N7B N6B C5B 121.9(3) . . ?
N6B N7B C3B 103.6(3) . . ?
O1B N8B C4B 117.5(3) . . ?
O2B N8B O1B 119.3(3) . . ?
O2B N8B C4B 123.2(3) . . ?
O3B N9B C4B 116.2(3) . . ?
O4B N9B O3B 120.6(3) . . ?
O4B N9B C4B 123.1(3) . . ?
N1B C1B N4B 112.1(4) . . ?
N1B C1B C2B 123.4(4) . . ?
N4B C1B C2B 124.5(4) . . ?
N5B C2B C1B 121.5(4) . . ?
N5B C2B C3B 108.7(3) . . ?
C3B C2B C1B 129.8(4) . . ?
N7B C3B C2B 108.1(3) . . ?
N7B C3B C4B 122.7(4) . . ?
C2B C3B C4B 129.2(4) . . ?
N8B C4B N9B 120.8(3) . . ?
N8B C4B C3B 119.9(3) . . ?
N9B C4B C3B 119.1(3) . . ?
N6B C5B H5BA 109.5 . . ?
N6B C5B H5BB 109.5 . . ?
N6B C5B H5BC 109.5 . . ?
H5BA C5B H5BB 109.5 . . ?
H5BA C5B H5BC 109.5 . . ?
H5BB C5B H5BC 109.5 . . ?
H4CA N4C H4CB 107(6) . . ?
H4CA N4C H4CC 102(6) . . ?
H4CA N4C H4CD 118(7) . . ?
H4CB N4C H4CC 106(6) . . ?
H4CB N4C H4CD 127(7) . . ?
H4CC N4C H4CD 91(7) . . ?
H3CA N3C H3CB 101(6) . . ?
H3CA N3C H3CC 119(7) . . ?
H3CA N3C H3CD 105(8) . . ?
H3CB N3C H3CC 116(6) . . ?
H3CB N3C H3CD 111(8) . . ?
H3CC N3C H3CD 105(8) . . ?
H2CA N2C H2CB 104(5) . . ?
H2CA N2C H2CC 116(6) . . ?
H2CA N2C H2CD 101(6) . . ?
H2CB N2C H2CC 114(5) . . ?
H2CB N2C H2CD 113(5) . . ?
H2CC N2C H2CD 108(5) . . ?
H1CA N1C H1CB 102(6) . . ?
H1CA N1C H1CC 109(6) . . ?
H1CA N1C H1CD 113(6) . . ?
H1CB N1C H1CC 107(6) . . ?
H1CB N1C H1CD 105(6) . . ?
H1CC N1C H1CD 118(6) . . ?
H1SA O1S H1SB 104.5 . . ?
H4SA O4S H4SB 107(7) . . ?
H2SA O2S H2SB 104(7) . . ?
H3SA O3S H3SB 104.5 . . ?

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
N4C H4CA O3S 0.96(3) 2.50(7) 3.024(6) 114(5) 1_455
N4C H4CB N2B 0.97(3) 2.08(4) 2.959(5) 150(5) .
N4C H4CC O3A 0.96(3) 2.14(5) 2.983(5) 146(6) 1_455
N4C H4CD O2B 0.97(3) 2.37(8) 2.855(5) 110(6) 1_565
N4C H4CD O4B 0.97(3) 2.19(7) 2.975(5) 137(7) 1_565
N3C H3CA N1B 0.84(3) 2.23(5) 2.942(5) 142(6) .
N3C H3CB O1B 0.84(3) 2.03(3) 2.846(5) 164(6) 2_666
N3C H3CC O2B 0.84(3) 2.13(4) 2.892(5) 151(6) 1_565
N3C H3CD O3A 0.84(3) 2.04(5) 2.832(5) 158(10) .
N2C H2CA O1A 0.89(3) 2.26(5) 2.940(5) 133(5) .
N2C H2CB N3B 0.89(3) 2.05(3) 2.932(5) 168(5) .
N2C H2CC O2S 0.89(3) 1.96(3) 2.850(6) 176(6) 1_545
N2C H2CD N1A 0.90(3) 2.01(3) 2.908(6) 173(6) 2_565
N1C H1CA O3B 0.88(3) 2.14(3) 3.001(5) 168(6) 1_665
N1C H1CB O3S 0.89(3) 1.92(3) 2.796(6) 170(5) .
N1C H1CC O4A 0.88(3) 2.17(5) 2.872(5) 136(5) .
N1C H1CD O4S 0.88(3) 2.01(4) 2.840(6) 156(6) .
O1S H1SA N4B 0.87 2.05 2.914(5) 170.6 1_565
O1S H1SB O4S 0.87 2.16 2.993(6) 160.7 .
O4S H4SA O2A 0.97(7) 1.97(7) 2.870(6) 153(6) 1_565
O4S H4SB N2A 0.71(8) 2.30(8) 3.001(6) 169(7) 2_675
O2S H2SA N3A 0.79(7) 2.13(7) 2.851(6) 151(7) 1_455
O2S H2SB N2A 0.83(8) 2.24(8) 3.033(5) 158(6) 2_675
O3S H3SA O1S 0.87 2.10 2.833(6) 141.5 1_655
O3S H3SA O2S 0.87 2.40 3.027(5) 129.4 1_655
O3S H3SB N4A 0.87 1.94 2.806(5) 171.7 .

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id He946
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shrv621
_database_code_depnum_ccdc_archive 'CCDC 1884770'
_audit_update_record             
;
2018-12-12 deposited with the CCDC.
2019-02-07 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 H3 N6 O4, K'
_chemical_formula_sum            'C5 H3 K N6 O4'
_chemical_formula_weight         250.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
K K 0.3868 1.0657 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   13.4341(3)
_cell_length_b                   8.8483(2)
_cell_length_c                   15.6056(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1855.02(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8388
_cell_measurement_theta_min      5.670
_cell_measurement_theta_max      74.485

_exptl_crystal_description       block
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    5.221
_shelx_estimated_absorpt_T_min   0.489
_shelx_estimated_absorpt_T_max   0.818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5741
_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            10436
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.670
_diffrn_reflns_theta_max         74.520
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1866
_reflns_number_gt                1730
_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)+(0.0415P)²+0.6886P] 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       0.0049(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1866
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0740
_refine_ls_wR_factor_gt          0.0720
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_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 0.86680(9) 0.38081(16) 0.61354(8) 0.0519(4) Uani 1 1 d . . . . .
O2 O 0.90284(8) 0.51533(14) 0.72500(8) 0.0458(3) Uani 1 1 d . . . . .
N3 N 0.84084(9) 0.47036(15) 0.67203(8) 0.0315(3) Uani 1 1 d . . . . .
C4 C 0.74198(10) 0.50909(17) 0.67411(8) 0.0270(3) Uani 1 1 d . . . . .
N5 N 0.70458(9) 0.60752(14) 0.73599(8) 0.0292(3) Uani 1 1 d . . . . .
O6 O 0.75839(9) 0.68646(14) 0.78138(8) 0.0437(3) Uani 1 1 d . . . . .
O7 O 0.61227(8) 0.61321(15) 0.74274(8) 0.0477(3) Uani 1 1 d . . . . .
C9 C 0.67408(10) 0.43981(15) 0.61281(8) 0.0259(3) Uani 1 1 d . . . . .
N10 N 0.59445(9) 0.35936(15) 0.63626(7) 0.0316(3) Uani 1 1 d . . . . .
N11 N 0.55131(9) 0.32073(15) 0.56301(7) 0.0315(3) Uani 1 1 d . . . . .
C12 C 0.46249(14) 0.2257(2) 0.56178(11) 0.0471(5) Uani 1 1 d . . . . .
H12A H 0.4268 0.2419 0.5093 0.071 Uiso 1 1 calc R U . . .
H12B H 0.4206 0.2512 0.6095 0.071 Uiso 1 1 calc R U . . .
H12C H 0.4817 0.1214 0.5658 0.071 Uiso 1 1 calc R U . . .
N13 N 0.59592(10) 0.36756(14) 0.49249(7) 0.0322(3) Uani 1 1 d . . . . .
C14 C 0.67490(11) 0.44404(16) 0.52290(9) 0.0282(3) Uani 1 1 d . . . . .
C15 C 0.74696(12) 0.51104(18) 0.46772(9) 0.0341(3) Uani 1 1 d . . . . .
N16 N 0.80631(13) 0.56517(18) 0.42560(10) 0.0490(4) Uani 1 1 d . . . . .
K17 K 0.94763(2) 0.78009(4) 0.81348(2) 0.03214(14) 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 1.2580(17) . ?
O2 N3 1.2391(17) . ?
N3 C4 1.3720(19) . ?
C4 N5 1.3941(18) . ?
C4 C9 1.4570(19) . ?
N5 O6 1.2297(16) . ?
N5 O7 1.2455(17) . ?
C9 N10 1.3360(18) . ?
C9 C14 1.4037(19) . ?
N10 N11 1.3265(16) . ?
N11 N13 1.3199(17) . ?
N11 C12 1.460(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N13 C14 1.3449(19) . ?
C14 C15 1.425(2) . ?
C15 N16 1.139(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
O2 N3 O1 119.99(13) . . ?
O2 N3 C4 123.69(12) . . ?
O1 N3 C4 116.29(12) . . ?
N3 C4 N5 121.42(13) . . ?
N3 C4 C9 119.04(12) . . ?
N5 C4 C9 119.47(12) . . ?
O6 N5 O7 120.91(12) . . ?
O6 N5 C4 122.82(12) . . ?
O7 N5 C4 116.27(12) . . ?
N10 C9 C14 107.12(12) . . ?
N10 C9 C4 123.06(12) . . ?
C14 C9 C4 129.80(13) . . ?
N11 N10 C9 104.54(11) . . ?
N13 N11 N10 116.06(12) . . ?
N13 N11 C12 122.75(12) . . ?
N10 N11 C12 121.13(12) . . ?
N11 C12 H12A 109.5 . . ?
N11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N11 N13 C14 102.83(11) . . ?
N13 C14 C9 109.45(12) . . ?
N13 C14 C15 122.15(13) . . ?
C9 C14 C15 128.36(13) . . ?
N16 C15 C14 178.03(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 2.0(2) . . . . ?
O1 N3 C4 N5 -179.98(14) . . . . ?
O2 N3 C4 C9 -174.98(14) . . . . ?
O1 N3 C4 C9 3.1(2) . . . . ?
N3 C4 N5 O6 13.9(2) . . . . ?
C9 C4 N5 O6 -169.13(13) . . . . ?
N3 C4 N5 O7 -166.83(14) . . . . ?
C9 C4 N5 O7 10.1(2) . . . . ?
N3 C4 C9 N10 121.57(16) . . . . ?
N5 C4 C9 N10 -55.4(2) . . . . ?
N3 C4 C9 C14 -60.1(2) . . . . ?
N5 C4 C9 C14 122.94(16) . . . . ?
C14 C9 N10 N11 -0.56(16) . . . . ?
C4 C9 N10 N11 178.13(13) . . . . ?
C9 N10 N11 N13 0.56(18) . . . . ?
C9 N10 N11 C12 177.65(15) . . . . ?
N10 N11 N13 C14 -0.29(17) . . . . ?
C12 N11 N13 C14 -177.33(15) . . . . ?
N11 N13 C14 C9 -0.10(16) . . . . ?
N11 N13 C14 C15 177.81(14) . . . . ?
N10 C9 C14 N13 0.43(16) . . . . ?
C4 C9 C14 N13 -178.15(14) . . . . ?
N10 C9 C14 C15 -177.31(15) . . . . ?
C4 C9 C14 C15 4.1(3) . . . . ?

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_shrv666
_database_code_depnum_ccdc_archive 'CCDC 1884771'
_audit_update_record             
;
2018-12-12 deposited with the CCDC.
2019-02-07 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 H3 N9 O4, 2(H5 N2)'
_chemical_formula_sum            'C5 H13 N13 O4'
_chemical_formula_weight         319.28

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.4845(2)
_cell_length_b                   12.8712(4)
_cell_length_c                   13.3363(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.3270(10)
_cell_angle_gamma                90
_cell_volume                     1284.40(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4416
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      28.33

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.106
_exptl_absorpt_coefficient_mu    0.140
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6957
_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            15040
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.199
_diffrn_reflns_theta_max         30.025
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3657
_reflns_number_gt                2763
_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)+(0.0659P)²+0.5200P] 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         3657
_refine_ls_number_parameters     215
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1351
_refine_ls_wR_factor_gt          0.1218
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.030
_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 0.38476(17) 0.51449(12) 0.38927(10) 0.0468(3) Uani 1 1 d . . . . .
O2 O 0.12982(17) 0.44199(11) 0.41517(9) 0.0443(3) Uani 1 1 d . . . . .
N3 N 0.25379(17) 0.46252(11) 0.35745(10) 0.0310(3) Uani 1 1 d . . . . .
C4 C 0.25774(19) 0.43072(12) 0.25903(11) 0.0276(3) Uani 1 1 d . . . . .
N5 N 0.12732(17) 0.36763(10) 0.21752(9) 0.0295(3) Uani 1 1 d . . . . .
O6 O -0.00210(16) 0.33352(11) 0.26489(9) 0.0428(3) Uani 1 1 d . . . . .
O7 O 0.14276(17) 0.34458(10) 0.12664(9) 0.0424(3) Uani 1 1 d . . . . .
C8 C 0.38898(19) 0.48039(11) 0.19501(11) 0.0271(3) Uani 1 1 d . . . . .
N9 N 0.54959(17) 0.44046(10) 0.17320(10) 0.0317(3) Uani 1 1 d . . . . .
N10 N 0.62236(16) 0.51361(10) 0.11681(10) 0.0293(3) Uani 1 1 d . . . . .
C11 C 0.8043(2) 0.50546(14) 0.08190(14) 0.0364(4) Uani 1 1 d . . . . .
H11A H 0.8177 0.5485 0.0238 0.055 Uiso 1 1 calc R U . . .
H11B H 0.8293 0.4345 0.0649 0.055 Uiso 1 1 calc R U . . .
H11C H 0.8862 0.5279 0.1340 0.055 Uiso 1 1 calc R U . . .
N12 N 0.52341(16) 0.59768(10) 0.10016(10) 0.0291(3) Uani 1 1 d . . . . .
C13 C 0.37328(18) 0.57794(11) 0.14967(11) 0.0257(3) Uani 1 1 d . . . . .
C14 C 0.22100(19) 0.64871(11) 0.15128(11) 0.0262(3) Uani 1 1 d . . . . .
N15 N 0.17213(18) 0.71277(11) 0.07732(10) 0.0335(3) Uani 1 1 d . . . . .
N16 N 0.02304(19) 0.75857(11) 0.11050(12) 0.0390(3) Uani 1 1 d . . . . .
N17 N -0.0143(2) 0.72260(12) 0.19901(12) 0.0411(3) Uani 1 1 d . . . . .
N18 N 0.10937(19) 0.65229(11) 0.22775(11) 0.0375(3) Uani 1 1 d . . . . .
N19 N -0.1609(3) 0.30988(16) 0.50292(16) 0.0580(5) Uani 1 1 d D . . . .
H19A H -0.248(3) 0.307(2) 0.5484(19) 0.087 Uiso 1 1 d D U . . .
H19B H -0.157(4) 0.2465(16) 0.471(2) 0.087 Uiso 1 1 d D U . . .
N20 N -0.2235(2) 0.38784(13) 0.43380(12) 0.0455(4) Uani 1 1 d . . . . .
H20A H -0.2346 0.4481 0.4659 0.068 Uiso 1 1 calc R U . . .
H20B H -0.3292 0.3689 0.4078 0.068 Uiso 1 1 calc R U . . .
H20C H -0.1456 0.3949 0.3848 0.068 Uiso 1 1 calc R U . . .
N21 N 0.2802(3) 0.37234(18) 0.64076(16) 0.0689(6) Uani 1 1 d D . . A 1
H21A H 0.283(4) 0.376(2) 0.7092(12) 0.103 Uiso 1 1 d D U . B 1
H21B H 0.388(3) 0.378(2) 0.618(2) 0.103 Uiso 1 1 d D U . C 1
N22 N 0.1802(2) 0.28586(13) 0.60684(13) 0.0519(4) Uani 1 1 d D . . A 1
H22A H 0.1694 0.2406 0.6568 0.078 Uiso 1 1 calc R U . A 1
H22B H 0.2360 0.2557 0.5563 0.078 Uiso 1 1 calc R U . A 1
H22C H 0.0723 0.3067 0.5860 0.078 Uiso 1 1 calc R U . A 1


_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 1.2527(17) . ?
O2 N3 1.2475(16) . ?
N3 C4 1.376(2) . ?
C4 N5 1.376(2) . ?
C4 C8 1.4633(19) . ?
N5 O6 1.2483(17) . ?
N5 O7 1.2557(17) . ?
C8 N9 1.3453(18) . ?
C8 C13 1.397(2) . ?
N9 N10 1.3295(17) . ?
N10 N12 1.3271(17) . ?
N10 C11 1.4532(19) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N12 C13 1.3407(18) . ?
C13 C14 1.460(2) . ?
C14 N15 1.330(2) . ?
C14 N18 1.3340(19) . ?
N15 N16 1.3459(19) . ?
N16 N17 1.304(2) . ?
N17 N18 1.344(2) . ?
N19 N20 1.434(3) . ?
N19 H19A 0.900(16) . ?
N19 H19B 0.918(16) . ?
N20 H20A 0.8900 . ?
N20 H20B 0.8900 . ?
N20 H20C 0.8900 . ?
N21 N22 1.410(3) . ?
N21 H21A 0.914(15) . ?
N21 H21B 0.874(15) . ?
N22 H22A 0.8900 . ?
N22 H22B 0.8900 . ?
N22 H22C 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
O2 N3 O1 119.43(13) . . ?
O2 N3 C4 123.95(13) . . ?
O1 N3 C4 116.62(12) . . ?
N3 C4 N5 121.91(12) . . ?
N3 C4 C8 117.14(13) . . ?
N5 C4 C8 120.17(13) . . ?
O6 N5 O7 119.68(14) . . ?
O6 N5 C4 123.75(13) . . ?
O7 N5 C4 116.57(13) . . ?
N9 C8 C13 108.44(12) . . ?
N9 C8 C4 125.06(13) . . ?
C13 C8 C4 126.46(13) . . ?
N10 N9 C8 103.39(12) . . ?
N12 N10 N9 115.96(12) . . ?
N12 N10 C11 121.92(12) . . ?
N9 N10 C11 121.96(13) . . ?
N10 C11 H11A 109.5 . . ?
N10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N10 N12 C13 103.52(12) . . ?
N12 C13 C8 108.69(12) . . ?
N12 C13 C14 123.55(13) . . ?
C8 C13 C14 127.75(13) . . ?
N15 C14 N18 112.28(13) . . ?
N15 C14 C13 125.25(13) . . ?
N18 C14 C13 122.41(13) . . ?
C14 N15 N16 104.09(13) . . ?
N17 N16 N15 109.81(13) . . ?
N16 N17 N18 109.65(13) . . ?
C14 N18 N17 104.17(13) . . ?
N20 N19 H19A 103(2) . . ?
N20 N19 H19B 110.0(19) . . ?
H19A N19 H19B 108(2) . . ?
N19 N20 H20A 109.5 . . ?
N19 N20 H20B 109.5 . . ?
H20A N20 H20B 109.5 . . ?
N19 N20 H20C 109.5 . . ?
H20A N20 H20C 109.5 . . ?
H20B N20 H20C 109.5 . . ?
N22 N21 H21A 111.0(15) . . ?
N22 N21 H21B 116.8(17) . . ?
H21A N21 H21B 110(2) . . ?
N21 N22 H22A 109.5 . . ?
N21 N22 H22B 109.5 . . ?
H22A N22 H22B 109.5 . . ?
N21 N22 H22C 109.5 . . ?
H22A N22 H22C 109.5 . . ?
H22B N22 H22C 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
O2 N3 C4 N5 -3.8(2) . . . . ?
O1 N3 C4 N5 175.72(14) . . . . ?
O2 N3 C4 C8 166.12(15) . . . . ?
O1 N3 C4 C8 -14.4(2) . . . . ?
N3 C4 N5 O6 -0.8(2) . . . . ?
C8 C4 N5 O6 -170.44(14) . . . . ?
N3 C4 N5 O7 179.00(14) . . . . ?
C8 C4 N5 O7 9.4(2) . . . . ?
N3 C4 C8 N9 97.64(18) . . . . ?
N5 C4 C8 N9 -92.26(19) . . . . ?
N3 C4 C8 C13 -79.6(2) . . . . ?
N5 C4 C8 C13 90.47(19) . . . . ?
C13 C8 N9 N10 -0.12(16) . . . . ?
C4 C8 N9 N10 -177.80(14) . . . . ?
C8 N9 N10 N12 0.11(18) . . . . ?
C8 N9 N10 C11 175.62(14) . . . . ?
N9 N10 N12 C13 -0.05(17) . . . . ?
C11 N10 N12 C13 -175.57(14) . . . . ?
N10 N12 C13 C8 -0.03(16) . . . . ?
N10 N12 C13 C14 -178.72(14) . . . . ?
N9 C8 C13 N12 0.10(17) . . . . ?
C4 C8 C13 N12 177.73(14) . . . . ?
N9 C8 C13 C14 178.72(14) . . . . ?
C4 C8 C13 C14 -3.6(3) . . . . ?
N12 C13 C14 N15 31.2(2) . . . . ?
C8 C13 C14 N15 -147.29(16) . . . . ?
N12 C13 C14 N18 -151.89(15) . . . . ?
C8 C13 C14 N18 29.7(2) . . . . ?
N18 C14 N15 N16 0.38(18) . . . . ?
C13 C14 N15 N16 177.60(14) . . . . ?
C14 N15 N16 N17 -0.48(18) . . . . ?
N15 N16 N17 N18 0.42(19) . . . . ?
N15 C14 N18 N17 -0.14(18) . . . . ?
C13 C14 N18 N17 -177.45(14) . . . . ?
N16 N17 N18 C14 -0.17(18) . . . . ?

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
C11 H11A O7 0.96 2.46 3.416(2) 178.5 3_665
C11 H11B N15 0.96 2.68 3.528(2) 147.4 3_665
C11 H11C N18 0.96 2.61 3.516(2) 157.1 1_655
N19 H19A O1 0.900(16) 2.65(2) 3.177(3) 118(2) 3_566
N19 H19A O7 0.900(16) 2.37(3) 2.991(2) 126(2) 4_566
N19 H19B N12 0.918(16) 2.371(18) 3.236(2) 157(2) 2_545
N20 H20A O1 0.89 2.31 2.956(2) 129.5 3_566
N20 H20A O2 0.89 2.25 3.046(2) 148.3 3_566
N20 H20A N3 0.89 2.63 3.397(2) 145.0 3_566
N20 H20B N16 0.89 2.04 2.843(2) 149.3 2_445
N20 H20B N17 0.89 2.62 3.369(2) 142.2 2_445
N20 H20C O2 0.89 2.18 2.7515(19) 121.7 .
N20 H20C O6 0.89 2.10 2.912(2) 151.1 .
N21 H21A N17 0.914(15) 2.69(2) 3.196(3) 115.6(16) 3_566
N21 H21B O1 0.874(15) 2.191(16) 2.935(2) 143(2) 3_666
N22 H22A N9 0.89 2.51 3.204(2) 135.4 4_566
N22 H22A N17 0.89 2.32 2.899(2) 122.9 3_566
N22 H22B N15 0.89 2.00 2.875(2) 166.1 2_545
N22 H22C N19 0.89 2.05 2.893(3) 158.8 .

_refine_diff_density_max         0.582
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.052

