# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

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

data_1
_audit_block_doi                 10.5517/ccdc.csd.cc20811d
_database_code_depnum_ccdc_archive 'CCDC 1854762'
_audit_update_record             
;
2018-07-10 deposited with the CCDC.
2018-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H N5 O5, H2 O'
_chemical_formula_sum            'C4 H3 N5 O6'
_chemical_formula_weight         217.11

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      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                   8.7552(8)
_cell_length_b                   8.1840(6)
_cell_length_c                   22.4827(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1610.9(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2293
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      25.34

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.169
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6247
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8681
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.526
_diffrn_reflns_theta_max         25.390
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1476
_reflns_number_gt                1018
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0396P)²+0.5049P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1476
_refine_ls_number_parameters     145
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5450(3) 0.7021(3) 0.69565(10) 0.0245(6) Uani 1 1 d . . . . .
C2 C 0.5091(3) 0.7954(3) 0.64435(10) 0.0226(6) Uani 1 1 d . . . . .
C3 C 0.5542(3) 0.9575(3) 0.62313(10) 0.0215(6) Uani 1 1 d . . . . .
C4 C 0.5467(3) 1.1805(3) 0.56996(10) 0.0240(6) Uani 1 1 d . . . . .
N1 N 0.4735(3) 0.5638(2) 0.69490(9) 0.0335(6) Uani 1 1 d . . . . .
N2 N 0.4131(3) 0.7108(2) 0.61251(9) 0.0316(5) Uani 1 1 d . . . . .
N3 N 0.6466(3) 0.7382(3) 0.74532(9) 0.0300(5) Uani 1 1 d . . . . .
N4 N 0.6690(3) 1.0396(2) 0.64303(9) 0.0286(5) Uani 1 1 d . . . . .
N5 N 0.4749(2) 1.0363(2) 0.57960(8) 0.0213(5) Uani 1 1 d . . . . .
H5 H 0.396(3) 1.005(3) 0.5580(10) 0.026 Uiso 1 1 d . U . . .
O1 O 0.3918(2) 0.5661(2) 0.64296(8) 0.0374(5) Uani 1 1 d . . . . .
O2 O 0.6173(3) 0.6745(3) 0.79289(8) 0.0517(6) Uani 1 1 d . . . . .
O3 O 0.7534(2) 0.8288(2) 0.73531(7) 0.0354(5) Uani 1 1 d . . . . .
O4 O 0.6649(2) 1.18671(18) 0.60904(7) 0.0293(5) Uani 1 1 d . . . . .
O5 O 0.5189(2) 1.28873(19) 0.53475(8) 0.0322(5) Uani 1 1 d . . . . .
O6 O 0.2633(2) 1.4766(2) 0.50722(8) 0.0278(4) Uani 1 1 d D . . . .
H6A H 0.314(3) 1.555(3) 0.4951(11) 0.033 Uiso 1 1 d D U . . .
H6B H 0.327(3) 1.410(3) 0.5156(11) 0.033 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.294(3) . ?
C1 C2 1.418(3) . ?
C1 N3 1.458(3) . ?
C2 N2 1.303(3) . ?
C2 C3 1.463(3) . ?
C3 N4 1.289(3) . ?
C3 N5 1.363(3) . ?
C4 O5 1.212(3) . ?
C4 N5 1.354(3) . ?
C4 O4 1.358(3) . ?
N1 O1 1.370(3) . ?
N2 O1 1.381(2) . ?
N3 O3 1.214(3) . ?
N3 O2 1.217(2) . ?
N4 O4 1.427(2) . ?
N5 H5 0.88(3) . ?
O6 H6A 0.828(17) . ?
O6 H6B 0.799(17) . ?

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 C1 C2 110.7(2) . . ?
N1 C1 N3 118.9(2) . . ?
C2 C1 N3 130.5(2) . . ?
N2 C2 C1 107.7(2) . . ?
N2 C2 C3 118.4(2) . . ?
C1 C2 C3 133.9(2) . . ?
N4 C3 N5 113.6(2) . . ?
N4 C3 C2 124.7(2) . . ?
N5 C3 C2 121.7(2) . . ?
O5 C4 N5 130.4(2) . . ?
O5 C4 O4 123.2(2) . . ?
N5 C4 O4 106.40(19) . . ?
C1 N1 O1 104.62(19) . . ?
C2 N2 O1 105.72(19) . . ?
O3 N3 O2 125.9(2) . . ?
O3 N3 C1 116.85(19) . . ?
O2 N3 C1 117.2(2) . . ?
C3 N4 O4 103.55(18) . . ?
C4 N5 C3 106.9(2) . . ?
C4 N5 H5 122.0(15) . . ?
C3 N5 H5 130.9(15) . . ?
N1 O1 N2 111.30(18) . . ?
C4 O4 N4 109.54(17) . . ?
H6A O6 H6B 104(3) . . ?

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1834718'
_audit_update_record             
;
2018-04-04 deposited with the CCDC.
2018-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H3 N5 O3, H2 O'
_chemical_formula_sum            'C4 H5 N5 O4'
_chemical_formula_weight         187.13

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                   8.6418(10)
_cell_length_b                   4.9850(5)
_cell_length_c                   17.235(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.095(3)
_cell_angle_gamma                90
_cell_volume                     720.13(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1157
_cell_measurement_theta_min      4.27
_cell_measurement_theta_max      25.23

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.154
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6801
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3996
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.867
_diffrn_reflns_theta_max         25.326
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1293
_reflns_number_gt                922
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0366P)²+0.3073P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1293
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.0930
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2085(3) 0.7099(5) 0.90417(13) 0.0146(5) Uani 1 1 d . . . . .
C2 C 0.1514(3) 0.9510(5) 0.79436(14) 0.0172(6) Uani 1 1 d . . . . .
C3 C 0.3017(3) 0.4923(5) 1.04387(14) 0.0175(5) Uani 1 1 d . . . . .
C4 C 0.2008(3) 0.5117(5) 0.96458(13) 0.0154(5) Uani 1 1 d . . . . .
N1 N 0.3225(2) 0.8859(4) 0.91588(11) 0.0189(5) Uani 1 1 d . . . . .
N2 N 0.1024(2) 0.7389(4) 0.83206(11) 0.0171(5) Uani 1 1 d . . . . .
H2A H 0.019(3) 0.637(5) 0.8105(14) 0.021 Uiso 1 1 d . U . . .
N3 N 0.2560(2) 0.2841(4) 1.07915(12) 0.0224(5) Uani 1 1 d . . . . .
N4 N 0.0953(2) 0.3203(4) 0.95272(12) 0.0206(5) Uani 1 1 d . . . . .
N5 N 0.4222(3) 0.6564(5) 1.07829(14) 0.0279(6) Uani 1 1 d . . . . .
H5A H 0.487(3) 0.610(6) 1.1271(17) 0.033 Uiso 1 1 d . U . . .
H5B H 0.446(3) 0.790(6) 1.0511(17) 0.033 Uiso 1 1 d . U . . .
O1 O 0.28749(18) 1.0448(3) 0.84539(9) 0.0198(4) Uani 1 1 d . . . . .
O2 O 0.12564(19) 0.1758(3) 1.02236(10) 0.0230(4) Uani 1 1 d . . . . .
O3 O 0.0952(2) 1.0528(3) 0.73021(10) 0.0233(5) Uani 1 1 d . . . . .
O4 O 0.8255(2) 0.5019(4) 0.73857(11) 0.0241(4) Uani 1 1 d . . . . .
H4C H 0.790(3) 0.370(6) 0.7590(16) 0.029 Uiso 1 1 d . U . . .
H4D H 0.827(3) 0.459(6) 0.6917(17) 0.029 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.298(3) . ?
C1 N2 1.361(3) . ?
C1 C4 1.449(3) . ?
C2 O3 1.206(3) . ?
C2 N2 1.361(3) . ?
C2 O1 1.368(3) . ?
C3 N3 1.311(3) . ?
C3 N5 1.343(3) . ?
C3 C4 1.434(3) . ?
C4 N4 1.300(3) . ?
N1 O1 1.420(2) . ?
N2 H2A 0.88(3) . ?
N3 O2 1.408(2) . ?
N4 O2 1.370(3) . ?
N5 H5A 0.92(3) . ?
N5 H5B 0.87(3) . ?
O4 H4C 0.84(3) . ?
O4 H4D 0.84(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
N1 C1 N2 112.8(2) . . ?
N1 C1 C4 121.0(2) . . ?
N2 C1 C4 126.2(2) . . ?
O3 C2 N2 131.5(2) . . ?
O3 C2 O1 122.4(2) . . ?
N2 C2 O1 106.1(2) . . ?
N3 C3 N5 124.5(2) . . ?
N3 C3 C4 108.3(2) . . ?
N5 C3 C4 127.3(2) . . ?
N4 C4 C3 109.9(2) . . ?
N4 C4 C1 122.7(2) . . ?
C3 C4 C1 127.4(2) . . ?
C1 N1 O1 104.40(17) . . ?
C1 N2 C2 107.5(2) . . ?
C1 N2 H2A 128.3(16) . . ?
C2 N2 H2A 124.2(16) . . ?
C3 N3 O2 105.16(18) . . ?
C4 N4 O2 105.72(18) . . ?
C3 N5 H5A 119.0(18) . . ?
C3 N5 H5B 119.2(18) . . ?
H5A N5 H5B 121(3) . . ?
C2 O1 N1 109.26(17) . . ?
N4 O2 N3 110.93(17) . . ?
H4C O4 H4D 107(3) . . ?

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1834720'
_audit_update_record             
;
2018-04-04 deposited with the CCDC.
2018-10-22 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         '2(H4 N), C4 N6 O5'
_chemical_formula_sum            'C4 H8 N8 O5'
_chemical_formula_weight         248.18

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

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

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

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

_cell_length_a                   8.9160(13)
_cell_length_b                   13.4685(15)
_cell_length_c                   8.1632(12)
_cell_angle_alpha                90
_cell_angle_beta                 97.542(5)
_cell_angle_gamma                90
_cell_volume                     971.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1013
_cell_measurement_theta_min      3.52
_cell_measurement_theta_max      25.01

_exptl_crystal_description       column
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.152
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6488
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5561
_diffrn_reflns_av_unetI/netI     0.0891
_diffrn_reflns_av_R_equivalents  0.0935
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.937
_diffrn_reflns_theta_max         25.353
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1765
_reflns_number_gt                979
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0352P)²+0.4318P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1765
_refine_ls_number_parameters     178
_refine_ls_number_restraints     94
_refine_ls_R_factor_all          0.1343
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1176
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5911(4) 0.2739(2) 1.0551(4) 0.0218(8) Uani 1 1 d . . . . .
C2 C 0.7250(4) 0.2730(2) 0.9738(4) 0.0218(8) Uani 1 1 d . . . . .
C3 C 0.8096(4) 0.1884(2) 0.9212(4) 0.0213(8) Uani 1 1 d . . . . .
C4 C 0.9680(4) 0.1054(2) 0.8067(4) 0.0247(9) Uani 1 1 d . . . . .
N1 N 0.5537(3) 0.36683(19) 1.0790(4) 0.0298(8) Uani 1 1 d . . . . .
N2 N 0.7665(3) 0.3636(2) 0.9473(4) 0.0291(8) Uani 1 1 d . . . . .
N3 N 0.5258(3) 0.18605(19) 1.0939(3) 0.0244(7) Uani 1 1 d . . . . .
N4 N 0.4037(3) 0.1922(2) 1.1708(4) 0.0297(8) Uani 1 1 d . . . . .
N5 N 0.7690(4) 0.0982(2) 0.9496(4) 0.0363(9) Uani 1 1 d . . . . .
N6 N 0.9306(3) 0.19871(19) 0.8360(4) 0.0240(7) Uani 1 1 d . . . . .
N7 N 0.6213(3) 0.96641(19) 0.1732(4) 0.0262(8) Uani 1 1 d D . . . .
H7A H 0.607(3) 1.0338(12) 0.149(3) 0.039 Uiso 1 1 d D U . . .
H7B H 0.7272(18) 0.9538(19) 0.204(3) 0.039 Uiso 1 1 d D U . . .
H7C H 0.586(3) 0.9274(17) 0.081(2) 0.039 Uiso 1 1 d D U . . .
H7D H 0.571(3) 0.9479(18) 0.264(3) 0.039 Uiso 1 1 d D U . . .
N8 N 0.9031(3) 0.8807(2) 0.6158(4) 0.0308(8) Uani 1 1 d D . . . .
H8A H 0.884(3) 0.887(2) 0.4991(19) 0.046 Uiso 1 1 d D U . . .
H8B H 0.809(2) 0.882(2) 0.657(3) 0.046 Uiso 1 1 d D U . . .
H8C H 0.965(3) 0.9325(16) 0.661(3) 0.046 Uiso 1 1 d D U . . .
H8D H 0.952(3) 0.8190(14) 0.642(3) 0.046 Uiso 1 1 d D U . . .
O1 O 0.6639(3) 0.42349(15) 1.0126(3) 0.0371(7) Uani 1 1 d . . . . .
O2 O 0.3475(3) 0.27084(17) 1.2122(3) 0.0438(8) Uani 1 1 d . . . . .
O3 O 0.3481(3) 0.10975(17) 1.2007(4) 0.0450(8) Uani 1 1 d . . . . .
O4 O 0.8748(3) 0.04084(16) 0.8752(3) 0.0396(7) Uani 1 1 d . . . . .
O5 O 1.0658(3) 0.06952(16) 0.7278(3) 0.0286(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.316(4) . ?
C1 N3 1.374(4) . ?
C1 C2 1.440(4) . ?
C2 N2 1.301(4) . ?
C2 C3 1.461(4) . ?
C3 N5 1.298(4) . ?
C3 N6 1.365(4) . ?
C4 O5 1.248(4) . ?
C4 N6 1.330(4) . ?
C4 O4 1.372(4) . ?
N1 O1 1.407(3) . ?
N2 O1 1.379(3) . ?
N3 N4 1.329(4) . ?
N4 O2 1.238(3) . ?
N4 O3 1.253(3) . ?
N5 O4 1.416(3) . ?
N7 H7A 0.934(15) . ?
N7 H7B 0.960(15) . ?
N7 H7C 0.937(15) . ?
N7 H7D 0.945(15) . ?
N8 H8A 0.950(15) . ?
N8 H8B 0.946(16) . ?
N8 H8C 0.937(16) . ?
N8 H8D 0.949(16) . ?

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 C1 N3 131.4(3) . . ?
N1 C1 C2 108.5(3) . . ?
N3 C1 C2 120.0(3) . . ?
N2 C2 C1 109.9(3) . . ?
N2 C2 C3 120.8(3) . . ?
C1 C2 C3 129.3(3) . . ?
N5 C3 N6 116.3(3) . . ?
N5 C3 C2 120.7(3) . . ?
N6 C3 C2 122.9(3) . . ?
O5 C4 N6 131.9(3) . . ?
O5 C4 O4 117.8(3) . . ?
N6 C4 O4 110.3(3) . . ?
C1 N1 O1 104.8(3) . . ?
C2 N2 O1 105.5(3) . . ?
N4 N3 C1 117.0(3) . . ?
O2 N4 O3 121.4(3) . . ?
O2 N4 N3 124.6(3) . . ?
O3 N4 N3 114.0(3) . . ?
C3 N5 O4 102.5(3) . . ?
C4 N6 C3 103.3(3) . . ?
H7A N7 H7B 109.0(15) . . ?
H7A N7 H7C 110.8(16) . . ?
H7B N7 H7C 108.9(16) . . ?
H7A N7 H7D 110.9(16) . . ?
H7B N7 H7D 107.3(15) . . ?
H7C N7 H7D 109.8(16) . . ?
H8A N8 H8B 108.0(16) . . ?
H8A N8 H8C 110.2(16) . . ?
H8B N8 H8C 110.8(16) . . ?
H8A N8 H8D 108.9(16) . . ?
H8B N8 H8D 109.4(16) . . ?
H8C N8 H8D 109.5(16) . . ?
N2 O1 N1 111.3(2) . . ?
C4 O4 N5 107.6(2) . . ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.068

