# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_shrv806
_database_code_depnum_ccdc_archive 'CCDC 1968919'
loop_
_audit_author_name
_audit_author_address
'Qiong Yu'
;University of Idaho
United States of America
;
_audit_update_record             
;
2019-11-29 deposited with the CCDC.	2020-03-06 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         'C3 N5 O7, K'
_chemical_formula_sum            'C3 K N5 O7'
_chemical_formula_weight         257.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

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

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

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

_cell_length_a                   10.266(3)
_cell_length_b                   7.180(2)
_cell_length_c                   12.384(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.643(13)
_cell_angle_gamma                90
_cell_volume                     836.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5273
_cell_measurement_theta_min      3.90
_cell_measurement_theta_max      74.36

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.043
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    6.057
_shelx_estimated_absorpt_T_min   0.392
_shelx_estimated_absorpt_T_max   0.713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4882
_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  'Montel multilayer optics'
_diffrn_measurement_device_type  'Photon II'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5640
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.702
_diffrn_reflns_theta_max         74.484
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             1603
_reflns_number_gt                1553
_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)+(0.0331P)²+0.2720P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'intrinsic phasing'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0163(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1603
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0705
_refine_ls_wR_factor_gt          0.0700
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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 0.17639(14) 0.33266(17) 0.72951(10) 0.0389(3) Uani 1 1 d . . . . .
O2 O 0.07502(13) 0.60173(17) 0.67964(11) 0.0373(3) Uani 1 1 d . . . . .
N3 N 0.14878(13) 0.47478(17) 0.66579(11) 0.0248(3) Uani 1 1 d . . . . .
C4 C 0.20179(15) 0.4809(2) 0.57992(13) 0.0252(3) Uani 1 1 d . . . . .
N5 N 0.17235(12) 0.62344(18) 0.49865(11) 0.0262(3) Uani 1 1 d . . . . .
O6 O 0.10121(13) 0.76206(16) 0.50086(10) 0.0368(3) Uani 1 1 d . . . . .
O7 O 0.21984(14) 0.60294(18) 0.42154(10) 0.0410(3) Uani 1 1 d . . . . .
C8 C 0.28276(15) 0.3217(2) 0.56735(13) 0.0265(3) Uani 1 1 d . . . . .
N9 N 0.22332(15) 0.1677(2) 0.51568(14) 0.0387(4) Uani 1 1 d . . . . .
O10 O 0.33282(14) 0.04957(18) 0.52377(14) 0.0472(4) Uani 1 1 d . . . . .
N11 N 0.46261(16) 0.1310(2) 0.58342(15) 0.0433(4) Uani 1 1 d . . . . .
C12 C 0.43177(16) 0.2949(2) 0.60881(14) 0.0309(4) Uani 1 1 d . . . . .
N13 N 0.54314(14) 0.4261(3) 0.67276(13) 0.0409(4) Uani 1 1 d . . . . .
O14 O 0.65285(13) 0.3644(3) 0.74659(13) 0.0603(4) Uani 1 1 d . . . . .
O15 O 0.51619(16) 0.5888(2) 0.64749(16) 0.0643(5) Uani 1 1 d . . . . .
K16 K 0.05357(3) 0.97628(5) 0.67537(3) 0.02953(15) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0535(7) 0.0291(6) 0.0362(6) 0.0081(5) 0.0201(6) 0.0028(5)
O2 0.0444(6) 0.0279(6) 0.0517(7) -0.0009(5) 0.0320(6) 0.0049(5)
N3 0.0246(6) 0.0220(6) 0.0282(6) -0.0016(5) 0.0109(5) -0.0024(5)
C4 0.0242(7) 0.0229(7) 0.0284(8) 0.0001(6) 0.0104(6) 0.0016(6)
N5 0.0232(6) 0.0272(7) 0.0253(6) 0.0001(5) 0.0069(5) -0.0020(5)
O6 0.0398(6) 0.0286(6) 0.0394(6) 0.0083(5) 0.0131(5) 0.0101(5)
O7 0.0492(7) 0.0475(8) 0.0331(6) 0.0031(5) 0.0237(6) -0.0009(6)
C8 0.0251(7) 0.0266(8) 0.0273(7) -0.0013(6) 0.0100(6) 0.0011(6)
N9 0.0318(7) 0.0297(7) 0.0524(9) -0.0092(6) 0.0148(6) 0.0029(6)
O10 0.0414(7) 0.0345(7) 0.0668(9) -0.0149(6) 0.0228(6) 0.0065(6)
N11 0.0346(7) 0.0446(9) 0.0522(9) -0.0045(7) 0.0190(7) 0.0101(7)
C12 0.0257(7) 0.0364(9) 0.0316(8) -0.0020(6) 0.0124(6) 0.0038(6)
N13 0.0257(7) 0.0575(11) 0.0396(8) -0.0089(7) 0.0132(6) -0.0042(7)
O14 0.0249(6) 0.0985(13) 0.0481(8) 0.0036(8) 0.0047(6) -0.0020(7)
O15 0.0476(8) 0.0484(10) 0.0852(11) -0.0156(8) 0.0143(8) -0.0111(7)
K16 0.0341(2) 0.0248(2) 0.0299(2) -0.00008(12) 0.01305(15) 0.00335(12)

_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 1.2509(17) . ?
O2 N3 1.2401(17) . ?
N3 C4 1.376(2) . ?
C4 N5 1.381(2) . ?
C4 C8 1.458(2) . ?
N5 O6 1.2412(18) . ?
N5 O7 1.2429(18) . ?
C8 N9 1.300(2) . ?
C8 C12 1.418(2) . ?
N9 O10 1.3795(18) . ?
O10 N11 1.369(2) . ?
N11 C12 1.290(2) . ?
C12 N13 1.448(2) . ?
N13 O15 1.212(3) . ?
N13 O14 1.214(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 120.58(13) . . ?
O2 N3 C4 122.43(12) . . ?
O1 N3 C4 116.99(12) . . ?
N3 C4 N5 123.23(13) . . ?
N3 C4 C8 118.47(13) . . ?
N5 C4 C8 118.07(13) . . ?
O6 N5 O7 121.84(13) . . ?
O6 N5 C4 122.47(13) . . ?
O7 N5 C4 115.69(13) . . ?
N9 C8 C12 106.73(14) . . ?
N9 C8 C4 122.96(13) . . ?
C12 C8 C4 130.27(14) . . ?
C8 N9 O10 106.21(13) . . ?
N11 O10 N9 111.42(12) . . ?
C12 N11 O10 103.89(13) . . ?
N11 C12 C8 111.73(15) . . ?
N11 C12 N13 120.66(15) . . ?
C8 C12 N13 127.61(15) . . ?
O15 N13 O14 126.35(18) . . ?
O15 N13 C12 115.94(14) . . ?
O14 N13 C12 117.71(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N3 C4 N5 -3.1(2) . . . . ?
O1 N3 C4 N5 175.82(13) . . . . ?
O2 N3 C4 C8 -177.61(13) . . . . ?
O1 N3 C4 C8 1.35(19) . . . . ?
N3 C4 N5 O6 3.7(2) . . . . ?
C8 C4 N5 O6 178.22(13) . . . . ?
N3 C4 N5 O7 -175.17(14) . . . . ?
C8 C4 N5 O7 -0.68(19) . . . . ?
N3 C4 C8 N9 77.5(2) . . . . ?
N5 C4 C8 N9 -97.22(19) . . . . ?
N3 C4 C8 C12 -99.55(19) . . . . ?
N5 C4 C8 C12 85.7(2) . . . . ?
C12 C8 N9 O10 -0.69(18) . . . . ?
C4 C8 N9 O10 -178.37(14) . . . . ?
C8 N9 O10 N11 1.1(2) . . . . ?
N9 O10 N11 C12 -1.0(2) . . . . ?
O10 N11 C12 C8 0.53(19) . . . . ?
O10 N11 C12 N13 -179.75(15) . . . . ?
N9 C8 C12 N11 0.1(2) . . . . ?
C4 C8 C12 N11 177.56(16) . . . . ?
N9 C8 C12 N13 -179.59(16) . . . . ?
C4 C8 C12 N13 -2.1(3) . . . . ?
N11 C12 N13 O15 146.63(18) . . . . ?
C8 C12 N13 O15 -33.7(2) . . . . ?
N11 C12 N13 O14 -34.1(2) . . . . ?
C8 C12 N13 O14 145.57(17) . . . . ?

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_19jms01_a
_database_code_depnum_ccdc_archive 'CCDC 1968921'
loop_
_audit_author_name
_audit_author_address
'Qiong Yu'
;University of Idaho
United States of America
;
_audit_update_record             
;
2019-11-29 deposited with the CCDC.	2020-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H N5 O7'
_chemical_formula_sum            'C3 H N5 O7'
_chemical_formula_weight         219.09

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   18.1742(7)
_cell_length_b                   6.6529(3)
_cell_length_c                   6.1535(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     744.03(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4959
_cell_measurement_theta_min      4.87
_cell_measurement_theta_max      74.66

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.048
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_max          0.144
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.956
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?

_exptl_absorpt_coefficient_mu    1.754
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_T_min  0.6394
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker AXS)
;

_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microsource IuS Incoatec 3.0'
_diffrn_detector                 'Bruker Photon II CPAD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray

_diffrn_reflns_number            6540
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         4.866
_diffrn_reflns_theta_max         74.655
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             1465
_reflns_number_gt                1424
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_max     0.900
_reflns_Friedel_fraction_full    0.927

_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       'APEX3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All non-hydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. The C-H
 hydrogen atom wasplaced in a calculated position with Uiso = 1.2xUeqiv
 of the connected C atom.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0685P)²+0.4316P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 591 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1465
_refine_ls_number_parameters     136
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1122
_refine_ls_wR_factor_gt          0.1113
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 0.38918(14) 0.2883(4) 0.2661(5) 0.0325(6) Uani 1 1 d . . . . .
O2 O 0.53310(14) 0.7362(4) 0.1866(6) 0.0362(7) Uani 1 1 d . . . . .
O3 O 0.45839(14) 0.9015(4) 0.3948(5) 0.0304(6) Uani 1 1 d . . . . .
O4 O 0.39682(15) 0.7266(5) 0.8151(5) 0.0362(7) Uani 1 1 d . . . . .
O5 O 0.33388(16) 1.0002(4) 0.7480(5) 0.0346(6) Uani 1 1 d . . . . .
O6 O 0.30957(13) 0.8919(4) 0.2085(5) 0.0292(6) Uani 1 1 d . . . . .
O7 O 0.22237(15) 0.9431(5) 0.4408(5) 0.0386(7) Uani 1 1 d . . . . .
N1 N 0.44550(18) 0.4140(5) 0.2155(6) 0.0299(7) Uani 1 1 d . . . . .
N2 N 0.33697(16) 0.3810(4) 0.3904(6) 0.0285(7) Uani 1 1 d . . . . .
N3 N 0.47784(17) 0.7546(4) 0.2930(6) 0.0261(6) Uani 1 1 d . . . . .
N4 N 0.35215(16) 0.8274(5) 0.7162(5) 0.0279(6) Uani 1 1 d . . . . .
N5 N 0.27933(14) 0.8620(4) 0.3827(5) 0.0231(6) Uani 1 1 d . . . . .
C1 C 0.42877(18) 0.5811(5) 0.3064(6) 0.0218(7) Uani 1 1 d . . . . .
C2 C 0.36018(19) 0.5654(5) 0.4175(6) 0.0248(7) Uani 1 1 d . . . . .
C3 C 0.3122(2) 0.7112(5) 0.5346(6) 0.0268(8) Uani 1 1 d . . . . .
H3 H 0.271011 0.634074 0.602632 0.032 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0300(13) 0.0306(12) 0.0367(17) 0.0002(11) -0.0065(12) 0.0003(10)
O2 0.0253(13) 0.0434(15) 0.0399(18) 0.0034(12) 0.0088(12) -0.0012(10)
O3 0.0296(13) 0.0286(12) 0.0330(15) -0.0017(11) 0.0057(11) -0.0010(9)
O4 0.0241(12) 0.0572(18) 0.0272(15) 0.0081(12) -0.0001(11) 0.0060(12)
O5 0.0383(14) 0.0394(14) 0.0261(15) 0.0001(11) 0.0043(11) -0.0039(11)
O6 0.0275(13) 0.0370(14) 0.0231(13) 0.0091(10) 0.0061(11) 0.0034(9)
O7 0.0282(13) 0.0565(18) 0.0310(17) 0.0045(13) 0.0085(11) 0.0139(12)
N1 0.0282(14) 0.0314(15) 0.0301(17) 0.0007(13) -0.0048(13) 0.0024(12)
N2 0.0264(14) 0.0286(14) 0.0304(17) 0.0072(14) -0.0049(13) 0.0008(11)
N3 0.0285(14) 0.0289(14) 0.0208(15) 0.0002(12) 0.0016(14) 0.0025(12)
N4 0.0221(12) 0.0432(17) 0.0184(15) 0.0048(13) 0.0045(12) 0.0009(12)
N5 0.0203(13) 0.0259(13) 0.0231(15) 0.0008(12) 0.0019(12) 0.0007(9)
C1 0.0226(15) 0.0256(15) 0.0172(15) 0.0021(12) -0.0014(12) 0.0024(13)
C2 0.0238(14) 0.0289(16) 0.0217(17) 0.0021(14) -0.0005(14) 0.0010(12)
C3 0.0254(17) 0.0317(19) 0.0233(19) 0.0037(15) 0.0022(14) 0.0020(13)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.358(4) . ?
O1 N2 1.366(4) . ?
O2 N3 1.205(4) . ?
O3 N3 1.213(4) . ?
O4 N4 1.216(4) . ?
O5 N4 1.212(4) . ?
O6 N5 1.221(4) . ?
O7 N5 1.221(4) . ?
N1 C1 1.281(5) . ?
N2 C2 1.308(5) . ?
N3 C1 1.461(4) . ?
N4 C3 1.540(5) . ?
N5 C3 1.496(5) . ?
C1 C2 1.426(5) . ?
C2 C3 1.490(5) . ?
C3 H3 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O1 N2 112.0(3) . . ?
C1 N1 O1 104.8(3) . . ?
C2 N2 O1 105.7(3) . . ?
O2 N3 O3 127.2(3) . . ?
O2 N3 C1 117.3(3) . . ?
O3 N3 C1 115.4(3) . . ?
O5 N4 O4 128.7(4) . . ?
O5 N4 C3 117.6(3) . . ?
O4 N4 C3 113.6(3) . . ?
O6 N5 O7 124.5(3) . . ?
O6 N5 C3 118.6(3) . . ?
O7 N5 C3 116.9(3) . . ?
N1 C1 C2 110.7(3) . . ?
N1 C1 N3 121.1(3) . . ?
C2 C1 N3 128.2(3) . . ?
N2 C2 C1 106.8(3) . . ?
N2 C2 C3 118.9(3) . . ?
C1 C2 C3 134.1(3) . . ?
C2 C3 N5 111.6(3) . . ?
C2 C3 N4 113.7(3) . . ?
N5 C3 N4 107.8(3) . . ?
C2 C3 H3 107.8 . . ?
N5 C3 H3 107.8 . . ?
N4 C3 H3 107.8 . . ?

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
N2 O1 N1 C1 0.0(4) . . . . ?
N1 O1 N2 C2 0.3(4) . . . . ?
O1 N1 C1 C2 -0.3(4) . . . . ?
O1 N1 C1 N3 178.4(3) . . . . ?
O2 N3 C1 N1 2.7(5) . . . . ?
O3 N3 C1 N1 -176.2(4) . . . . ?
O2 N3 C1 C2 -178.8(4) . . . . ?
O3 N3 C1 C2 2.3(5) . . . . ?
O1 N2 C2 C1 -0.5(4) . . . . ?
O1 N2 C2 C3 175.7(3) . . . . ?
N1 C1 C2 N2 0.5(4) . . . . ?
N3 C1 C2 N2 -178.1(3) . . . . ?
N1 C1 C2 C3 -174.8(4) . . . . ?
N3 C1 C2 C3 6.6(6) . . . . ?
N2 C2 C3 N5 -107.3(4) . . . . ?
C1 C2 C3 N5 67.5(5) . . . . ?
N2 C2 C3 N4 130.5(3) . . . . ?
C1 C2 C3 N4 -54.7(5) . . . . ?
O6 N5 C3 C2 -21.9(4) . . . . ?
O7 N5 C3 C2 156.2(3) . . . . ?
O6 N5 C3 N4 103.7(3) . . . . ?
O7 N5 C3 N4 -78.2(4) . . . . ?
O5 N4 C3 C2 145.6(3) . . . . ?
O4 N4 C3 C2 -37.1(4) . . . . ?
O5 N4 C3 N5 21.3(4) . . . . ?
O4 N4 C3 N5 -161.4(3) . . . . ?

_refine_diff_density_max         0.517
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.073

_shelx_res_file                  
;
TITL X:\Users\JMS\19jms01\work\19jms01_a.res in Pna2(1)
    X:\Users\JMS\19jms01\work\19jms01_a.res
    created by SHELXL-2018/3 at 13:40:59 on 27-Sep-2019
CELL 1.54178 18.1742 6.6529 6.1535 90.000 90.000 90.000
ZERR 4.0000 0.0007 0.0003 0.0003 0.000 0.000 0.000
LATT -1
SYMM -X, -Y, 0.5+Z
SYMM 0.5-X, 0.5+Y, 0.5+Z
SYMM 0.5+X, 0.5-Y, Z
SFAC C H N O
UNIT 12 4 20 28
BOND $H
conf
ACTA
FMAP 2 1 53
PLAN 20 0 0
LIST 2 1
TEMP -100
L.S. 10
WGHT    0.068500    0.431600
FVAR       0.67391
O1    4    0.389179    0.288298    0.266082    11.00000    0.03002    0.03062 =
         0.03671    0.00019   -0.00647    0.00030
O2    4    0.533100    0.736158    0.186557    11.00000    0.02533    0.04340 =
         0.03995    0.00344    0.00878   -0.00121
O3    4    0.458394    0.901487    0.394816    11.00000    0.02956    0.02857 =
         0.03300   -0.00175    0.00574   -0.00096
O4    4    0.396820    0.726649    0.815063    11.00000    0.02408    0.05723 =
         0.02716    0.00813   -0.00014    0.00598
O5    4    0.333882    1.000166    0.747973    11.00000    0.03831    0.03939 =
         0.02607    0.00008    0.00427   -0.00389
O6    4    0.309565    0.891879    0.208519    11.00000    0.02746    0.03698 =
         0.02305    0.00913    0.00610    0.00340
O7    4    0.222373    0.943084    0.440839    11.00000    0.02822    0.05650 =
         0.03105    0.00452    0.00855    0.01390
N1    3    0.445496    0.413990    0.215543    11.00000    0.02825    0.03143 =
         0.03010    0.00069   -0.00477    0.00238
N2    3    0.336965    0.380971    0.390444    11.00000    0.02644    0.02862 =
         0.03039    0.00722   -0.00489    0.00081
N3    3    0.477839    0.754599    0.293043    11.00000    0.02849    0.02893 =
         0.02076    0.00021    0.00165    0.00251
N4    3    0.352151    0.827387    0.716215    11.00000    0.02209    0.04319 =
         0.01836    0.00482    0.00455    0.00093
N5    3    0.279331    0.861986    0.382699    11.00000    0.02028    0.02593 =
         0.02308    0.00082    0.00190    0.00072
C1    1    0.428767    0.581113    0.306407    11.00000    0.02256    0.02555 =
         0.01718    0.00209   -0.00136    0.00238
C2    1    0.360175    0.565404    0.417496    11.00000    0.02380    0.02885 =
         0.02171    0.00214   -0.00049    0.00101
C3    1    0.312229    0.711224    0.534573    11.00000    0.02542    0.03170 =
         0.02330    0.00371    0.00217    0.00201
AFIX  13
H3    2    0.271011    0.634074    0.602632    11.00000   -1.20000
AFIX   0
HKLF 4




REM  X:\Users\JMS\19jms01\work\19jms01_a.res in Pna2(1)
REM wR2 = 0.1122, GooF = S = 1.079, Restrained GooF = 1.079 for all data
REM R1 = 0.0436 for 1424 Fo > 4sig(Fo) and 0.0445 for all 1465 data
REM 136 parameters refined using 1 restraints

END

WGHT      0.0685      0.4316

REM Highest difference peak  0.517,  deepest hole -0.195,  1-sigma level  0.073
Q1    1   0.4995  0.5994  0.2205  11.00000  0.05    0.52
Q2    1   0.4177  0.7341  0.4180  11.00000  0.05    0.49
Q3    1   0.3994  0.4066  0.2591  11.00000  0.05    0.44
Q4    1   0.4053  0.8591  0.8698  11.00000  0.05    0.41
Q5    1   0.2212  0.8024  0.4665  11.00000  0.05    0.37
Q6    1   0.4230  0.2626  0.1215  11.00000  0.05    0.36
Q7    1   0.5197  0.8047  0.3106  11.00000  0.05    0.29
Q8    1   0.3548  0.9390  0.7398  11.00000  0.05    0.25
Q9    1   0.4414  0.6552  0.2811  11.00000  0.05    0.24
Q10   1   0.4356  0.5312  0.2546  11.00000  0.05    0.24
Q11   1   0.3503  0.7035  0.4045  11.00000  0.05    0.23
Q12   1   0.3531  0.7444  0.5528  11.00000  0.05    0.22
Q13   1   0.3373  0.2492  0.3995  11.00000  0.05    0.22
Q14   1   0.3120  0.7663  0.2187  11.00000  0.05    0.21
Q15   1   0.4031  0.5745  0.3866  11.00000  0.05    0.21
Q16   1   0.2838  0.7256  0.3938  11.00000  0.05    0.21
Q17   1   0.3357  1.0624  0.7708  11.00000  0.05    0.20
Q18   1   0.4049  0.8803  0.3727  11.00000  0.05    0.20
Q19   1   0.2801  1.0138  0.3878  11.00000  0.05    0.20
Q20   1   0.4132  0.8616  0.7426  11.00000  0.05    0.19
;
_shelx_res_checksum              89634
####################################################################### 
# 
# 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_shrv782
_database_code_depnum_ccdc_archive 'CCDC 1968922'
loop_
_audit_author_name
_audit_author_address
'Qiong Yu'
;University of Idaho
United States of America
;
_audit_update_record             
;
2019-11-29 deposited with the CCDC.	2020-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 N8 O8'
_chemical_formula_sum            'C6 N8 O8'
_chemical_formula_weight         312.14

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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   6.754(3)
_cell_length_b                   10.796(4)
_cell_length_c                   15.179(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1106.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3032
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      21.82

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.873
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.057
_exptl_absorpt_coefficient_mu    0.176
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6912
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   ?
_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            12914
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.315
_diffrn_reflns_theta_max         30.018
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3152
_reflns_number_gt                2157
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_max     0.958
_reflns_Friedel_fraction_full    1.000

_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)+(0.0400P)²+0.1375P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'intrinsic phasing'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 721 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3152
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0933
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 0.1635(4) 0.6280(3) 0.37763(19) 0.0860(8) Uani 1 1 d . . . . .
O2 O 0.3336(5) 0.7453(3) 0.2915(2) 0.1236(12) Uani 1 1 d . . . . .
N3 N 0.3141(5) 0.6607(3) 0.34247(17) 0.0654(7) Uani 1 1 d . . . . .
C4 C 0.4893(4) 0.5879(2) 0.36253(16) 0.0448(6) Uani 1 1 d . . . . .
N5 N 0.5997(4) 0.5486(3) 0.29925(15) 0.0618(7) Uani 1 1 d . . . . .
O6 O 0.7387(3) 0.4746(2) 0.33933(12) 0.0606(5) Uani 1 1 d . . . . .
N7 N 0.7106(3) 0.4720(2) 0.42903(12) 0.0437(5) Uani 1 1 d . . . . .
C8 C 0.5564(3) 0.5414(2) 0.44443(15) 0.0354(5) Uani 1 1 d . . . . .
C9 C 0.4892(3) 0.5595(2) 0.53371(14) 0.0354(5) Uani 1 1 d . . . . .
N10 N 0.3847(3) 0.6574(2) 0.55858(14) 0.0453(5) Uani 1 1 d . . . . .
O11 O 0.3245(3) 0.7503(2) 0.52224(14) 0.0662(6) Uani 1 1 d . . . . .
O12 O 0.3419(3) 0.64285(19) 0.65086(12) 0.0568(5) Uani 1 1 d . . . . .
N13 N 0.4250(3) 0.5335(2) 0.67837(13) 0.0519(6) Uani 1 1 d . . . . .
C14 C 0.5127(3) 0.4858(2) 0.60987(14) 0.0372(5) Uani 1 1 d . . . . .
C15 C 0.6116(4) 0.3649(2) 0.61804(15) 0.0385(5) Uani 1 1 d . . . . .
N16 N 0.5126(4) 0.2674(2) 0.64208(16) 0.0578(6) Uani 1 1 d . . . . .
O17 O 0.6487(4) 0.1724(2) 0.64381(15) 0.0713(6) Uani 1 1 d . . . . .
N18 N 0.8332(4) 0.2122(2) 0.62002(16) 0.0592(7) Uani 1 1 d . . . . .
C19 C 0.8100(4) 0.3293(2) 0.60406(15) 0.0419(6) Uani 1 1 d . . . . .
N20 N 0.9785(3) 0.4044(2) 0.58004(15) 0.0516(6) Uani 1 1 d . . . . .
O21 O 1.1250(3) 0.3524(3) 0.55251(18) 0.0839(7) Uani 1 1 d . . . . .
O22 O 0.9581(3) 0.5154(2) 0.58937(14) 0.0646(6) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0667(15) 0.095(2) 0.0968(18) -0.0098(16) -0.0102(15) 0.0225(15)
O2 0.149(3) 0.105(2) 0.117(2) 0.0560(19) -0.039(2) 0.020(2)
N3 0.081(2) 0.0584(16) 0.0568(14) 0.0042(13) -0.0258(15) 0.0090(15)
C4 0.0567(15) 0.0373(13) 0.0403(12) 0.0032(11) -0.0056(12) -0.0013(12)
N5 0.0812(17) 0.0641(16) 0.0401(11) 0.0071(11) 0.0040(12) 0.0016(15)
O6 0.0693(12) 0.0705(14) 0.0420(10) -0.0028(9) 0.0117(9) 0.0117(12)
N7 0.0499(11) 0.0444(12) 0.0369(10) -0.0012(9) 0.0048(9) 0.0024(11)
C8 0.0401(12) 0.0268(10) 0.0393(11) -0.0012(10) -0.0003(10) -0.0020(10)
C9 0.0354(11) 0.0299(11) 0.0409(12) -0.0034(9) -0.0010(10) 0.0010(10)
N10 0.0490(11) 0.0367(11) 0.0500(12) -0.0078(10) -0.0045(10) 0.0079(10)
O11 0.0804(15) 0.0419(11) 0.0764(15) -0.0040(10) -0.0135(12) 0.0204(11)
O12 0.0585(11) 0.0590(13) 0.0530(10) -0.0178(9) 0.0085(10) 0.0123(11)
N13 0.0560(13) 0.0559(15) 0.0437(12) -0.0043(11) 0.0059(10) 0.0052(12)
C14 0.0379(11) 0.0399(13) 0.0340(10) -0.0028(10) 0.0017(10) -0.0019(10)
C15 0.0451(12) 0.0395(13) 0.0308(10) 0.0036(10) -0.0005(10) -0.0011(11)
N16 0.0649(15) 0.0456(13) 0.0629(14) 0.0165(12) 0.0076(13) -0.0041(12)
O17 0.0876(16) 0.0430(11) 0.0833(14) 0.0242(10) 0.0041(13) 0.0022(11)
N18 0.0659(16) 0.0483(14) 0.0633(15) 0.0093(12) -0.0093(14) 0.0123(13)
C19 0.0466(14) 0.0428(14) 0.0364(12) 0.0018(10) -0.0061(11) 0.0032(11)
N20 0.0430(12) 0.0630(16) 0.0488(12) -0.0001(11) -0.0092(11) 0.0002(12)
O21 0.0413(10) 0.106(2) 0.1045(17) -0.0104(16) 0.0032(12) 0.0108(13)
O22 0.0633(13) 0.0591(14) 0.0713(13) 0.0002(11) -0.0034(10) -0.0156(11)

_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 1.202(3) . ?
O2 N3 1.204(4) . ?
N3 C4 1.453(4) . ?
C4 N5 1.288(4) . ?
C4 C8 1.415(3) . ?
N5 O6 1.374(3) . ?
O6 N7 1.375(3) . ?
N7 C8 1.304(3) . ?
C8 C9 1.442(3) . ?
C9 N10 1.326(3) . ?
C9 C14 1.412(3) . ?
N10 O11 1.215(3) . ?
N10 O12 1.439(3) . ?
O12 N13 1.372(3) . ?
N13 C14 1.303(3) . ?
C14 C15 1.471(3) . ?
C15 N16 1.300(3) . ?
C15 C19 1.411(4) . ?
N16 O17 1.377(3) . ?
O17 N18 1.366(3) . ?
N18 C19 1.297(3) . ?
C19 N20 1.444(3) . ?
N20 O21 1.212(3) . ?
N20 O22 1.215(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N3 O2 126.9(3) . . ?
O1 N3 C4 115.9(3) . . ?
O2 N3 C4 117.1(3) . . ?
N5 C4 C8 110.6(2) . . ?
N5 C4 N3 119.6(2) . . ?
C8 C4 N3 129.5(2) . . ?
C4 N5 O6 104.9(2) . . ?
N5 O6 N7 110.86(19) . . ?
C8 N7 O6 106.01(19) . . ?
N7 C8 C4 107.6(2) . . ?
N7 C8 C9 119.8(2) . . ?
C4 C8 C9 132.6(2) . . ?
N10 C9 C14 106.0(2) . . ?
N10 C9 C8 122.9(2) . . ?
C14 C9 C8 131.1(2) . . ?
O11 N10 C9 135.0(2) . . ?
O11 N10 O12 117.7(2) . . ?
C9 N10 O12 107.3(2) . . ?
N13 O12 N10 107.95(17) . . ?
C14 N13 O12 106.4(2) . . ?
N13 C14 C9 112.3(2) . . ?
N13 C14 C15 119.3(2) . . ?
C9 C14 C15 128.3(2) . . ?
N16 C15 C19 108.0(2) . . ?
N16 C15 C14 120.6(2) . . ?
C19 C15 C14 131.3(2) . . ?
C15 N16 O17 105.4(2) . . ?
N18 O17 N16 111.72(19) . . ?
C19 N18 O17 104.2(2) . . ?
N18 C19 C15 110.6(2) . . ?
N18 C19 N20 120.0(3) . . ?
C15 C19 N20 129.3(2) . . ?
O21 N20 O22 126.1(3) . . ?
O21 N20 C19 118.1(3) . . ?
O22 N20 C19 115.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N3 C4 N5 130.5(3) . . . . ?
O2 N3 C4 N5 -48.1(4) . . . . ?
O1 N3 C4 C8 -43.6(4) . . . . ?
O2 N3 C4 C8 137.8(3) . . . . ?
C8 C4 N5 O6 0.7(3) . . . . ?
N3 C4 N5 O6 -174.5(2) . . . . ?
C4 N5 O6 N7 -0.9(3) . . . . ?
N5 O6 N7 C8 0.8(3) . . . . ?
O6 N7 C8 C4 -0.3(3) . . . . ?
O6 N7 C8 C9 -179.0(2) . . . . ?
N5 C4 C8 N7 -0.2(3) . . . . ?
N3 C4 C8 N7 174.3(3) . . . . ?
N5 C4 C8 C9 178.3(3) . . . . ?
N3 C4 C8 C9 -7.2(5) . . . . ?
N7 C8 C9 N10 155.7(2) . . . . ?
C4 C8 C9 N10 -22.6(4) . . . . ?
N7 C8 C9 C14 -24.8(4) . . . . ?
C4 C8 C9 C14 156.9(3) . . . . ?
C14 C9 N10 O11 178.5(3) . . . . ?
C8 C9 N10 O11 -1.9(4) . . . . ?
C14 C9 N10 O12 -0.6(3) . . . . ?
C8 C9 N10 O12 179.0(2) . . . . ?
O11 N10 O12 N13 -179.2(2) . . . . ?
C9 N10 O12 N13 0.0(3) . . . . ?
N10 O12 N13 C14 0.6(3) . . . . ?
O12 N13 C14 C9 -1.1(3) . . . . ?
O12 N13 C14 C15 -178.2(2) . . . . ?
N10 C9 C14 N13 1.1(3) . . . . ?
C8 C9 C14 N13 -178.5(2) . . . . ?
N10 C9 C14 C15 177.9(2) . . . . ?
C8 C9 C14 C15 -1.7(4) . . . . ?
N13 C14 C15 N16 59.0(3) . . . . ?
C9 C14 C15 N16 -117.6(3) . . . . ?
N13 C14 C15 C19 -120.9(3) . . . . ?
C9 C14 C15 C19 62.5(4) . . . . ?
C19 C15 N16 O17 0.6(3) . . . . ?
C14 C15 N16 O17 -179.4(2) . . . . ?
C15 N16 O17 N18 -0.4(3) . . . . ?
N16 O17 N18 C19 0.0(3) . . . . ?
O17 N18 C19 C15 0.3(3) . . . . ?
O17 N18 C19 N20 177.5(2) . . . . ?
N16 C15 C19 N18 -0.6(3) . . . . ?
C14 C15 C19 N18 179.3(2) . . . . ?
N16 C15 C19 N20 -177.4(2) . . . . ?
C14 C15 C19 N20 2.5(4) . . . . ?
N18 C19 N20 O21 19.5(4) . . . . ?
C15 C19 N20 O21 -163.9(3) . . . . ?
N18 C19 N20 O22 -160.8(2) . . . . ?
C15 C19 N20 O22 15.8(4) . . . . ?

_refine_diff_density_max         0.234
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.033
####################################################################### 
# 
# 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_shrv783
_database_code_depnum_ccdc_archive 'CCDC 1968920'
loop_
_audit_author_name
_audit_author_address
'Qiong Yu'
;University of Idaho
United States of America
;
_audit_update_record             
;
2019-11-29 deposited with the CCDC.	2020-03-06 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         'C3 N5 O7, H4 N O'
_chemical_formula_sum            'C3 H4 N6 O8'
_chemical_formula_weight         252.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   23.5598(10)
_cell_length_b                   6.4371(3)
_cell_length_c                   15.9786(7)
_cell_angle_alpha                90
_cell_angle_beta                 130.7954(11)
_cell_angle_gamma                90
_cell_volume                     1834.52(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2278
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      24.59

_exptl_crystal_description       chunk
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.063
_exptl_absorpt_coefficient_mu    0.181
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6985
_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            10560
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.284
_diffrn_reflns_theta_max         30.019
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2596
_reflns_number_gt                1633
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_special_details          
;
One nitro oxygen displayed two-componennt disorder.  Each component 
was fixed at half occupancy.  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0423P)²+0.9637P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_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         2596
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1073
_refine_ls_wR_factor_gt          0.0918
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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 0.47804(6) 0.5895(2) 0.11117(13) 0.0757(5) Uani 1 1 d . . . . .
O2 O 0.53587(6) 0.78897(19) 0.08056(10) 0.0556(4) Uani 1 1 d . . . . .
N3 N 0.53698(7) 0.6481(2) 0.13441(11) 0.0427(3) Uani 1 1 d . . . . .
C4 C 0.60204(8) 0.5519(2) 0.22203(12) 0.0363(3) Uani 1 1 d . . . . .
N5 N 0.67176(6) 0.61306(19) 0.26246(10) 0.0376(3) Uani 1 1 d . . . . .
O6 O 0.68289(6) 0.7605(2) 0.22504(11) 0.0594(4) Uani 1 1 d . . . . .
O7 O 0.72566(6) 0.50886(18) 0.34159(9) 0.0460(3) Uani 1 1 d . . . . .
C8 C 0.59912(8) 0.3720(2) 0.27422(13) 0.0406(4) Uani 1 1 d . . . . .
N9 N 0.56552(10) 0.1996(2) 0.22105(14) 0.0668(5) Uani 1 1 d . . . . .
O10 O 0.57848(9) 0.0633(2) 0.29902(13) 0.0792(5) Uani 1 1 d . . . . .
N11 N 0.62070(10) 0.1537(3) 0.40088(16) 0.0642(5) Uani 1 1 d . . . . .
C12 C 0.63273(9) 0.3392(3) 0.38520(14) 0.0440(4) Uani 1 1 d . . . . .
N13 N 0.67609(10) 0.4856(3) 0.47645(13) 0.0647(5) Uani 1 1 d . . . . .
O14 O 0.66966(8) 0.6664(2) 0.45330(11) 0.0631(4) Uani 1 1 d . . . . .
O15A O 0.7312(3) 0.4346(11) 0.5712(5) 0.0870(17) Uani 0.5 1 d . . P A 1
O15B O 0.6931(4) 0.3958(11) 0.5610(5) 0.107(2) Uani 0.5 1 d . . P A 2
N16 N 0.62422(7) 0.08344(19) 0.07100(10) 0.0362(3) Uani 1 1 d . . . . .
H16A H 0.6511 0.0501 0.0519 0.054 Uiso 1 1 calc R U . . .
H16B H 0.5790 0.1264 0.0115 0.054 Uiso 1 1 calc R U . . .
H16C H 0.6196 -0.0274 0.0994 0.054 Uiso 1 1 calc R U . . .
O17 O 0.66014(8) 0.2417(2) 0.14927(13) 0.0684(4) Uani 1 1 d . . . . .
H17 H 0.7123(16) 0.224(4) 0.186(2) 0.103 Uiso 1 1 d . U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0314(6) 0.0901(11) 0.0869(10) 0.0343(9) 0.0305(7) 0.0058(7)
O2 0.0416(6) 0.0555(7) 0.0525(7) 0.0224(6) 0.0232(6) 0.0056(5)
N3 0.0326(6) 0.0442(7) 0.0440(7) 0.0081(6) 0.0218(6) 0.0043(6)
C4 0.0296(7) 0.0374(8) 0.0380(8) 0.0067(6) 0.0205(6) 0.0034(6)
N5 0.0324(6) 0.0393(7) 0.0391(7) 0.0047(6) 0.0225(6) 0.0027(5)
O6 0.0408(6) 0.0626(8) 0.0648(8) 0.0260(7) 0.0301(6) -0.0016(6)
O7 0.0301(5) 0.0511(7) 0.0461(6) 0.0119(5) 0.0202(5) 0.0084(5)
C8 0.0349(7) 0.0397(8) 0.0466(9) 0.0056(7) 0.0265(7) 0.0026(6)
N9 0.0735(11) 0.0472(9) 0.0641(10) 0.0056(8) 0.0381(9) -0.0121(8)
O10 0.0853(10) 0.0532(8) 0.0857(11) 0.0157(8) 0.0500(9) -0.0121(8)
N11 0.0722(11) 0.0600(10) 0.0767(12) 0.0269(9) 0.0558(10) 0.0171(9)
C12 0.0475(9) 0.0432(9) 0.0514(10) 0.0151(8) 0.0367(8) 0.0169(7)
N13 0.0754(11) 0.0687(11) 0.0461(9) 0.0111(8) 0.0380(9) 0.0341(9)
O14 0.0718(9) 0.0610(8) 0.0656(9) -0.0058(7) 0.0488(8) -0.0002(7)
O15A 0.090(3) 0.089(3) 0.0399(18) 0.0133(19) 0.024(2) 0.030(3)
O15B 0.157(6) 0.090(3) 0.053(3) 0.014(2) 0.059(4) 0.029(4)
N16 0.0346(6) 0.0379(7) 0.0357(6) 0.0060(5) 0.0228(5) 0.0048(5)
O17 0.0469(7) 0.0708(9) 0.0811(10) -0.0305(8) 0.0390(7) -0.0072(7)

_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(17) . ?
O2 N3 1.2386(17) . ?
N3 C4 1.3741(18) . ?
C4 N5 1.3725(18) . ?
C4 C8 1.455(2) . ?
N5 O6 1.2379(17) . ?
N5 O7 1.2503(15) . ?
C8 N9 1.304(2) . ?
C8 C12 1.408(2) . ?
N9 O10 1.385(2) . ?
O10 N11 1.364(2) . ?
N11 C12 1.289(2) . ?
C12 N13 1.453(2) . ?
N13 O14 1.200(2) . ?
N13 O15A 1.232(6) . ?
N13 O15B 1.269(6) . ?
N16 O17 1.3910(18) . ?
N16 H16A 0.8900 . ?
N16 H16B 0.8900 . ?
N16 H16C 0.8900 . ?
O17 H17 0.96(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N3 O1 120.26(13) . . ?
O2 N3 C4 122.74(13) . . ?
O1 N3 C4 117.00(13) . . ?
N5 C4 N3 123.07(13) . . ?
N5 C4 C8 116.66(12) . . ?
N3 C4 C8 120.24(13) . . ?
O6 N5 O7 120.27(12) . . ?
O6 N5 C4 123.96(12) . . ?
O7 N5 C4 115.77(12) . . ?
N9 C8 C12 107.18(15) . . ?
N9 C8 C4 122.67(15) . . ?
C12 C8 C4 130.03(15) . . ?
C8 N9 O10 105.66(15) . . ?
N11 O10 N9 111.30(14) . . ?
C12 N11 O10 104.17(15) . . ?
N11 C12 C8 111.69(17) . . ?
N11 C12 N13 120.36(16) . . ?
C8 C12 N13 127.95(15) . . ?
O14 N13 O15A 117.2(4) . . ?
O14 N13 O15B 131.1(4) . . ?
O14 N13 C12 117.06(15) . . ?
O15A N13 C12 123.1(4) . . ?
O15B N13 C12 107.4(4) . . ?
O17 N16 H16A 109.5 . . ?
O17 N16 H16B 109.5 . . ?
H16A N16 H16B 109.5 . . ?
O17 N16 H16C 109.5 . . ?
H16A N16 H16C 109.5 . . ?
H16B N16 H16C 109.5 . . ?
N16 O17 H17 104.4(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 C4 N5 4.8(3) . . . . ?
O1 N3 C4 N5 -174.40(16) . . . . ?
O2 N3 C4 C8 -173.03(15) . . . . ?
O1 N3 C4 C8 7.8(2) . . . . ?
N3 C4 N5 O6 0.7(2) . . . . ?
C8 C4 N5 O6 178.56(15) . . . . ?
N3 C4 N5 O7 -179.08(14) . . . . ?
C8 C4 N5 O7 -1.2(2) . . . . ?
N5 C4 C8 N9 -116.76(18) . . . . ?
N3 C4 C8 N9 61.2(2) . . . . ?
N5 C4 C8 C12 58.9(2) . . . . ?
N3 C4 C8 C12 -123.19(18) . . . . ?
C12 C8 N9 O10 0.1(2) . . . . ?
C4 C8 N9 O10 176.60(15) . . . . ?
C8 N9 O10 N11 -0.2(2) . . . . ?
N9 O10 N11 C12 0.3(2) . . . . ?
O10 N11 C12 C8 -0.18(19) . . . . ?
O10 N11 C12 N13 179.46(15) . . . . ?
N9 C8 C12 N11 0.0(2) . . . . ?
C4 C8 C12 N11 -176.10(16) . . . . ?
N9 C8 C12 N13 -179.56(16) . . . . ?
C4 C8 C12 N13 4.3(3) . . . . ?
N11 C12 N13 O14 -161.46(17) . . . . ?
C8 C12 N13 O14 18.1(3) . . . . ?
N11 C12 N13 O15A 37.7(4) . . . . ?
C8 C12 N13 O15A -142.7(4) . . . . ?
N11 C12 N13 O15B -2.4(4) . . . . ?
C8 C12 N13 O15B 177.2(4) . . . . ?

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
N16 H16A O7 0.89 2.22 2.8697(16) 129.2 4_645
N16 H16A O14 0.89 2.63 3.1478(18) 118.2 6_565
N16 H16A N11 0.89 2.41 3.071(2) 131.5 6
N16 H16B O2 0.89 2.14 2.9715(17) 155.2 5_665
N16 H16B N3 0.89 2.59 3.4488(17) 163.8 5_665
N16 H16B O1 0.89 2.36 3.0895(18) 139.8 5_665
N16 H16C O2 0.89 2.15 2.8920(18) 141.1 1_545
N16 H16C O6 0.89 2.05 2.8007(16) 141.3 1_545
O17 H17 O7 0.96(3) 2.26(3) 2.9987(18) 133(2) 4_645
O17 H17 O6 0.96(3) 1.89(3) 2.8318(18) 165(2) 4_645
O17 H17 N5 0.96(3) 2.39(3) 3.3257(18) 164(2) 4_645

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.039

# start Validation Reply Form
_vrf_PLAT015_shrv783             
;
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
