# 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 2017

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1042137'
_audit_update_record             
;
2017-05-11 deposited with the CCDC.
2017-05-19 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 H6 N8 O13'
_chemical_formula_sum            'C5 H6 N8 O13'
_chemical_formula_weight         386.18

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      orthorhombic
_space_group_IT_number           34
_space_group_name_H-M_alt        'P n n 2'
_space_group_name_Hall           'P 2 -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'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   10.396(2)
_cell_length_b                   11.229(2)
_cell_length_c                   5.8102(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     678.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    427
_cell_measurement_theta_min      3.63
_cell_measurement_theta_max      20.72

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.891
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.189
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6733
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'APEX2 CCD detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2265
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.670
_diffrn_reflns_theta_max         26.456
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_point_group_measured_fraction_full 0.912
_reflns_number_total             1251
_reflns_number_gt                888
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_max     0.792
_reflns_Friedel_fraction_full    0.814

_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       'APEX2 (Bruker, 2011)'
_computing_cell_refinement       APEX2
_computing_data_reduction        APEX2
_computing_structure_solution    'SHELXS (Bruker, 2000)'
_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)+(0.0380P)²] 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_abs_structure_details 
;
 Flack x determined using 275 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.8(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1251
_refine_ls_number_parameters     122
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.0960
_refine_ls_wR_factor_gt          0.0834
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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 1.0000 0.5000 0.9570(15) 0.0245(17) Uani 1 2 d S T P . .
C2 C 0.8360(4) 0.6550(4) 0.9271(10) 0.0228(11) Uani 1 1 d . . . . .
H2A H 0.8392 0.6456 1.0965 0.027 Uiso 1 1 calc R U . . .
H2B H 0.7483 0.6337 0.8749 0.027 Uiso 1 1 calc R U . . .
C3 C 0.8642(4) 0.7836(4) 0.8642(8) 0.0193(11) Uani 1 1 d . . . . .
N1 N 0.9283(4) 0.5762(4) 0.8216(7) 0.0230(10) Uani 1 1 d . . . . .
H1 H 0.933(4) 0.563(5) 0.679(9) 0.028 Uiso 1 1 d . U . . .
N2 N 0.7885(4) 0.8719(3) 1.0066(7) 0.0279(11) Uani 1 1 d . . . . .
N3 N 0.8294(4) 0.8139(4) 0.6145(7) 0.0280(10) Uani 1 1 d . . . . .
N4 N 1.0051(4) 0.8137(4) 0.8938(9) 0.0266(10) Uani 1 1 d . . . . .
O1 O 1.0000 0.5000 1.1649(10) 0.0305(13) Uani 1 2 d S T P . .
O2 O 0.8431(3) 0.9591(3) 1.0809(7) 0.0394(10) Uani 1 1 d . . . . .
O3 O 0.6743(3) 0.8460(3) 1.0304(7) 0.0374(11) Uani 1 1 d . . . . .
O4 O 0.8475(4) 0.7348(3) 0.4753(6) 0.0389(10) Uani 1 1 d . . . . .
O5 O 0.7880(4) 0.9127(4) 0.5757(8) 0.0465(10) Uani 1 1 d . . . . .
O6 O 1.0605(3) 0.8623(3) 0.7364(7) 0.0386(11) Uani 1 1 d . . . . .
O7 O 1.0501(3) 0.7839(3) 1.0782(8) 0.0387(10) 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 O1 1.208(8) . ?
C1 N1 1.380(6) . ?
C1 N1 1.380(6) 2_765 ?
C2 N1 1.443(6) . ?
C2 C3 1.519(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N2 1.512(6) . ?
C3 N4 1.513(5) . ?
C3 N3 1.534(6) . ?
N1 H1 0.84(5) . ?
N2 O2 1.211(5) . ?
N2 O3 1.231(5) . ?
N3 O5 1.211(5) . ?
N3 O4 1.216(5) . ?
N4 O6 1.210(6) . ?
N4 O7 1.216(6) . ?

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 C1 N1 124.7(4) . . ?
O1 C1 N1 124.7(4) . 2_765 ?
N1 C1 N1 110.5(7) . 2_765 ?
N1 C2 C3 110.6(4) . . ?
N1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
N2 C3 N4 107.2(4) . . ?
N2 C3 C2 113.0(4) . . ?
N4 C3 C2 111.9(4) . . ?
N2 C3 N3 104.4(3) . . ?
N4 C3 N3 106.6(4) . . ?
C2 C3 N3 113.1(4) . . ?
C1 N1 C2 119.8(5) . . ?
C1 N1 H1 115(4) . . ?
C2 N1 H1 124(3) . . ?
O2 N2 O3 127.1(4) . . ?
O2 N2 C3 118.8(4) . . ?
O3 N2 C3 114.1(4) . . ?
O5 N3 O4 126.9(5) . . ?
O5 N3 C3 117.6(4) . . ?
O4 N3 C3 115.5(4) . . ?
O6 N4 O7 127.4(4) . . ?
O6 N4 C3 118.4(4) . . ?
O7 N4 C3 114.2(4) . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1042138'
_audit_update_record             
;
2017-05-11 deposited with the CCDC.
2017-05-19 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 H5 N7 O7'
_chemical_formula_sum            'C4 H5 N7 O7'
_chemical_formula_weight         263.15

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                   8.8179(15)
_cell_length_b                   9.2863(16)
_cell_length_c                   11.802(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.562(4)
_cell_angle_gamma                90
_cell_volume                     946.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    479
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      22.44

_exptl_crystal_description       column
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.175
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6549
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'APEX2 CCD detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4659
_diffrn_reflns_av_unetI/netI     0.1016
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.358
_diffrn_reflns_theta_max         26.280
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1895
_reflns_number_gt                1049
_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       'APEX2 (Bruker, 2011)'
_computing_cell_refinement       APEX2
_computing_data_reduction        APEX2
_computing_structure_solution    'SHELXS (Bruker, 2000)'
_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)+(0.0183P)²+0.1151P] 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         1895
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1190
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.0878
_refine_ls_wR_factor_gt          0.0728
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.5675(3) 0.3206(3) 0.6162(3) 0.0148(7) Uani 1 1 d . . . . .
C2 C 0.7235(3) 0.2410(3) 0.5212(3) 0.0176(7) Uani 1 1 d . . . . .
C3 C 0.4104(3) 0.3897(3) 0.7545(3) 0.0171(7) Uani 1 1 d . . . . .
H3A H 0.4118 0.4903 0.7824 0.021 Uiso 1 1 calc R U . . .
H3B H 0.4945 0.3368 0.8061 0.021 Uiso 1 1 calc R U . . .
C4 C 0.2552(3) 0.3210(3) 0.7619(3) 0.0165(7) Uani 1 1 d . . . . .
N1 N 0.6572(3) 0.2395(3) 0.6935(2) 0.0190(7) Uani 1 1 d . . . . .
N2 N 0.6032(3) 0.3281(3) 0.5090(2) 0.0167(6) Uani 1 1 d . . . . .
N3 N 0.4397(3) 0.3889(3) 0.6390(2) 0.0178(6) Uani 1 1 d . . . . .
H3 H 0.409(3) 0.466(3) 0.597(2) 0.021 Uiso 1 1 d . U . . .
N4 N 0.1165(3) 0.4183(3) 0.7174(3) 0.0234(7) Uani 1 1 d . . . . .
N5 N 0.2263(3) 0.1826(3) 0.6931(2) 0.0215(7) Uani 1 1 d . . . . .
N6 N 0.2482(3) 0.2835(3) 0.8857(2) 0.0241(7) Uani 1 1 d . . . . .
N7 N 0.8044(3) 0.2045(3) 0.4424(2) 0.0242(7) Uani 1 1 d . . . . .
H7A H 0.875(3) 0.144(3) 0.460(3) 0.029 Uiso 1 1 d . U . . .
H7B H 0.774(3) 0.226(3) 0.372(3) 0.029 Uiso 1 1 d . U . . .
O1 O 0.7669(2) 0.1845(2) 0.62765(18) 0.0211(5) Uani 1 1 d . . . . .
O2 O 0.1281(2) 0.4957(3) 0.6373(2) 0.0334(7) Uani 1 1 d . . . . .
O3 O 0.0074(2) 0.4096(3) 0.7670(2) 0.0361(7) Uani 1 1 d . . . . .
O4 O 0.1039(2) 0.1691(2) 0.62384(19) 0.0286(6) Uani 1 1 d . . . . .
O5 O 0.3306(2) 0.0951(2) 0.71376(19) 0.0273(6) Uani 1 1 d . . . . .
O6 O 0.1918(3) 0.1695(3) 0.9053(2) 0.0391(7) Uani 1 1 d . . . . .
O7 O 0.3030(3) 0.3763(3) 0.9560(2) 0.0333(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 1.317(4) . ?
C1 N3 1.366(4) . ?
C1 N2 1.366(4) . ?
C2 N2 1.319(4) . ?
C2 N7 1.325(4) . ?
C2 O1 1.345(3) . ?
C3 N3 1.438(4) . ?
C3 C4 1.528(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N6 1.515(4) . ?
C4 N5 1.514(4) . ?
C4 N4 1.527(4) . ?
N1 O1 1.449(3) . ?
N3 H3 0.88(3) . ?
N4 O2 1.208(3) . ?
N4 O3 1.224(3) . ?
N5 O5 1.215(3) . ?
N5 O4 1.223(3) . ?
N6 O6 1.212(3) . ?
N6 O7 1.226(3) . ?
N7 H7A 0.83(3) . ?
N7 H7B 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 N3 122.3(3) . . ?
N1 C1 N2 116.9(3) . . ?
N3 C1 N2 120.7(3) . . ?
N2 C2 N7 128.0(3) . . ?
N2 C2 O1 114.4(3) . . ?
N7 C2 O1 117.6(3) . . ?
N3 C3 C4 112.6(2) . . ?
N3 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
N3 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
N6 C4 N5 106.7(2) . . ?
N6 C4 N4 106.4(2) . . ?
N5 C4 N4 106.3(2) . . ?
N6 C4 C3 111.1(2) . . ?
N5 C4 C3 112.4(2) . . ?
N4 C4 C3 113.5(3) . . ?
C1 N1 O1 101.7(2) . . ?
C2 N2 C1 101.4(3) . . ?
C1 N3 C3 120.0(3) . . ?
C1 N3 H3 116.1(19) . . ?
C3 N3 H3 116(2) . . ?
O2 N4 O3 127.7(3) . . ?
O2 N4 C4 115.7(3) . . ?
O3 N4 C4 116.6(3) . . ?
O5 N5 O4 126.6(3) . . ?
O5 N5 C4 114.9(2) . . ?
O4 N5 C4 118.5(2) . . ?
O6 N6 O7 127.3(3) . . ?
O6 N6 C4 118.8(3) . . ?
O7 N6 C4 113.9(3) . . ?
C2 N7 H7A 119(2) . . ?
C2 N7 H7B 121(2) . . ?
H7A N7 H7B 118(3) . . ?
C2 O1 N1 105.5(2) . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1042139'
_audit_update_record             
;
2017-05-11 deposited with the CCDC.
2017-05-19 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT089_2                   
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       5.55 Note  
RESPONSE: The compound crystallized in a noncentrosymmetric space group 
P2(1) and the diffraction turns very weak at high angle (theta g.t. about 25.5 
deg.), leading to much more parameters (than those in centrosymmetric ones) 
and less data used during structral refinement. 
;
# end Validation Reply Form

_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 H5 N7 O10'
_chemical_formula_sum            'C4 H5 N7 O10'
_chemical_formula_weight         311.15

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.1401(11)
_cell_length_b                   7.8040(13)
_cell_length_c                   10.6428(19)
_cell_angle_alpha                90
_cell_angle_beta                 109.113(3)
_cell_angle_gamma                90
_cell_volume                     560.34(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    713
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      21.57

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.844
_exptl_crystal_F_000             316
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.183
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6652
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'APEX2 CCD detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3208
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.025
_diffrn_reflns_theta_max         25.723
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             2028
_reflns_number_gt                1528
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.837
_reflns_Friedel_fraction_max     0.939
_reflns_Friedel_fraction_full    0.944

_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       'APEX2 (Bruker, 2011)'
_computing_cell_refinement       APEX2
_computing_data_reduction        APEX2
_computing_structure_solution    'SHELXS97 (Bruker, 2000)'
_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)+(0.0231P)²+0.2110P] 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_abs_structure_details 
;
 Flack x determined using 550 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.8(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2028
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0763
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 -0.3802(8) 1.1770(7) 0.7154(5) 0.0222(13) Uani 1 1 d . . . . .
C2 C -0.0271(8) 1.1471(6) 0.7362(5) 0.0221(13) Uani 1 1 d . . . . .
C3 C 0.1815(7) 0.9297(7) 0.8740(5) 0.0237(13) Uani 1 1 d . . . . .
H3A H 0.2110 0.9306 0.9716 0.028 Uiso 1 1 calc R U . . .
H3B H 0.2838 0.9993 0.8536 0.028 Uiso 1 1 calc R U . . .
C4 C 0.1918(7) 0.7475(7) 0.8282(5) 0.0206(12) Uani 1 1 d . . . . .
N1 N -0.5540(6) 1.2655(6) 0.6492(5) 0.0227(11) Uani 1 1 d . . . . .
H1 H -0.651(7) 1.240(8) 0.668(5) 0.027 Uiso 1 1 d . U . . .
N2 N -0.2121(6) 1.2282(6) 0.6924(4) 0.0214(11) Uani 1 1 d . . . . .
H2 H -0.219(8) 1.308(7) 0.643(6) 0.026 Uiso 1 1 d . U . . .
N3 N -0.0106(6) 1.0062(6) 0.8109(4) 0.0214(11) Uani 1 1 d . . . . .
H3 H -0.105(8) 0.970(7) 0.831(5) 0.026 Uiso 1 1 d . U . . .
N4 N -0.5845(7) 1.3940(6) 0.5571(4) 0.0260(11) Uani 1 1 d . . . . .
N5 N 0.1078(7) 0.7290(6) 0.6787(4) 0.0264(11) Uani 1 1 d . . . . .
N6 N 0.4064(7) 0.6882(6) 0.8729(5) 0.0303(12) Uani 1 1 d . . . . .
N7 N 0.0822(7) 0.6204(7) 0.8886(5) 0.0310(12) Uani 1 1 d . . . . .
O1 O -0.4424(5) 1.4552(6) 0.5323(4) 0.0419(12) Uani 1 1 d . . . . .
O2 O -0.7559(6) 1.4414(6) 0.5079(4) 0.0367(10) Uani 1 1 d . . . . .
O3 O -0.3917(5) 1.0622(5) 0.7892(4) 0.0292(10) Uani 1 1 d . . . . .
O4 O 0.1058(5) 1.2101(5) 0.7040(4) 0.0323(10) Uani 1 1 d . . . . .
O5 O -0.0278(6) 0.6278(6) 0.6337(4) 0.0364(11) Uani 1 1 d . . . . .
O6 O 0.1841(6) 0.8224(6) 0.6179(4) 0.0356(11) Uani 1 1 d . . . . .
O7 O 0.4586(6) 0.5970(6) 0.7981(4) 0.0516(14) Uani 1 1 d . . . . .
O8 O 0.5074(6) 0.7346(6) 0.9824(4) 0.0375(10) Uani 1 1 d . . . . .
O9 O 0.1512(6) 0.4785(5) 0.9148(4) 0.0452(12) Uani 1 1 d . . . . .
O10 O -0.0679(7) 0.6757(6) 0.9040(5) 0.0499(13) 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 O3 1.212(6) . ?
C1 N2 1.362(6) . ?
C1 N1 1.393(6) . ?
C2 O4 1.214(6) . ?
C2 N3 1.339(6) . ?
C2 N2 1.399(6) . ?
C3 N3 1.444(6) . ?
C3 C4 1.512(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N5 1.513(7) . ?
C4 N6 1.521(6) . ?
C4 N7 1.529(7) . ?
N1 N4 1.368(6) . ?
N1 H1 0.81(5) . ?
N2 H2 0.80(5) . ?
N3 H3 0.82(5) . ?
N4 O2 1.220(5) . ?
N4 O1 1.226(5) . ?
N5 O6 1.215(6) . ?
N5 O5 1.219(6) . ?
N6 O8 1.207(6) . ?
N6 O7 1.213(5) . ?
N7 O9 1.207(6) . ?
N7 O10 1.215(6) . ?

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
O3 C1 N2 125.8(5) . . ?
O3 C1 N1 117.2(5) . . ?
N2 C1 N1 117.1(5) . . ?
O4 C2 N3 125.1(5) . . ?
O4 C2 N2 117.5(5) . . ?
N3 C2 N2 117.3(5) . . ?
N3 C3 C4 112.2(4) . . ?
N3 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
N3 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C3 C4 N5 112.6(4) . . ?
C3 C4 N6 109.6(4) . . ?
N5 C4 N6 108.2(4) . . ?
C3 C4 N7 112.9(4) . . ?
N5 C4 N7 107.4(4) . . ?
N6 C4 N7 105.9(4) . . ?
N4 N1 C1 129.2(4) . . ?
N4 N1 H1 114(4) . . ?
C1 N1 H1 117(4) . . ?
C1 N2 C2 126.8(5) . . ?
C1 N2 H2 118(4) . . ?
C2 N2 H2 115(4) . . ?
C2 N3 C3 120.1(4) . . ?
C2 N3 H3 121(4) . . ?
C3 N3 H3 118(4) . . ?
O2 N4 O1 125.0(5) . . ?
O2 N4 N1 115.6(4) . . ?
O1 N4 N1 119.4(4) . . ?
O6 N5 O5 128.0(5) . . ?
O6 N5 C4 114.2(4) . . ?
O5 N5 C4 117.8(5) . . ?
O8 N6 O7 126.5(5) . . ?
O8 N6 C4 115.6(4) . . ?
O7 N6 C4 117.9(5) . . ?
O9 N7 O10 127.3(5) . . ?
O9 N7 C4 117.8(5) . . ?
O10 N7 C4 115.0(5) . . ?

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.053

