# Electronic Supplementary Material (ESI) for Materials Horizons.
# 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_ta_a
_database_code_depnum_ccdc_archive 'CCDC 1981076'
loop_
_audit_author_name
_audit_author_address
'Wang Zhang Yuan'
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2020-01-31 deposited with the CCDC.	2020-05-19 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         'C5 H8 N2 O2'
_chemical_formula_sum            'C5 H8 N2 O2'
_chemical_formula_weight         128.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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           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                   7.1989(6)
_cell_length_b                   7.2267(7)
_cell_length_c                   13.0042(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     676.53(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3357
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      68.07

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_F_000             272
_exptl_transmission_factor_min   0.6838
_exptl_transmission_factor_max   0.7530
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.833
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.865
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3499
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         11.075
_diffrn_reflns_theta_max         63.676
_diffrn_reflns_theta_full        63.676
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             1074
_reflns_number_gt                1056
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.630
_reflns_Friedel_fraction_max     0.941
_reflns_Friedel_fraction_full    0.941

_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0735P)²+0.0428P] 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 403 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1074
_refine_ls_number_parameters     84
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1046
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_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 0.36900(18) 0.2093(2) 0.48588(11) 0.0533(5) Uani 1 1 d . . . . .
C1 C 0.2680(3) 0.5868(3) 0.64844(17) 0.0509(6) Uani 1 1 d . . . . .
N1 N 0.2202(2) 0.4352(3) 0.57902(15) 0.0566(6) Uani 1 1 d . . . . .
H1 H 0.107902 0.408464 0.562017 0.068 Uiso 1 1 calc R U . . .
N2 N 0.5231(2) 0.4220(2) 0.58681(12) 0.0448(5) Uani 1 1 d . . . . .
H2 H 0.634747 0.387179 0.573322 0.054 Uiso 1 1 calc R U . . .
C2 C 0.4788(3) 0.5629(3) 0.65279(18) 0.0519(6) Uani 1 1 d . . . . .
O2 O 0.5870(3) 0.6525(3) 0.70318(17) 0.0843(7) Uani 1 1 d . . . . .
C3 C 0.3667(2) 0.3431(3) 0.54484(13) 0.0419(5) Uani 1 1 d . . . . .
C4 C 0.1809(4) 0.5610(4) 0.7532(2) 0.0747(8) Uani 1 1 d . . . . .
H4A H 0.048704 0.575421 0.747930 0.112 Uiso 1 1 calc R U . . .
H4B H 0.229684 0.651807 0.799825 0.112 Uiso 1 1 calc R U . . .
H4C H 0.209089 0.439318 0.778408 0.112 Uiso 1 1 calc R U . . .
C5 C 0.2223(4) 0.7741(4) 0.6022(3) 0.0827(9) Uani 1 1 d . . . . .
H5A H 0.271831 0.781027 0.533795 0.124 Uiso 1 1 calc R U . . .
H5B H 0.276280 0.869920 0.643732 0.124 Uiso 1 1 calc R U . . .
H5C H 0.089983 0.789883 0.599934 0.124 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.234(2) . ?
C1 N1 1.460(3) . ?
C1 C4 1.511(3) . ?
C1 C5 1.517(4) . ?
C1 C2 1.529(3) . ?
N1 C3 1.324(3) . ?
N1 H1 0.8600 . ?
N2 C2 1.369(3) . ?
N2 C3 1.375(2) . ?
N2 H2 0.8600 . ?
C2 O2 1.207(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?

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 C4 111.53(19) . . ?
N1 C1 C5 111.92(19) . . ?
C4 C1 C5 112.2(2) . . ?
N1 C1 C2 99.91(18) . . ?
C4 C1 C2 111.4(2) . . ?
C5 C1 C2 109.3(2) . . ?
C3 N1 C1 113.39(16) . . ?
C3 N1 H1 123.3 . . ?
C1 N1 H1 123.3 . . ?
C2 N2 C3 111.48(16) . . ?
C2 N2 H2 124.3 . . ?
C3 N2 H2 124.3 . . ?
O2 C2 N2 126.1(2) . . ?
O2 C2 C1 126.9(2) . . ?
N2 C2 C1 106.99(18) . . ?
O1 C3 N1 127.83(17) . . ?
O1 C3 N2 124.08(17) . . ?
N1 C3 N2 108.09(16) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C1 N1 C3 -119.9(2) . . . . ?
C5 C1 N1 C3 113.5(2) . . . . ?
C2 C1 N1 C3 -2.1(2) . . . . ?
C3 N2 C2 O2 177.3(2) . . . . ?
C3 N2 C2 C1 -3.8(2) . . . . ?
N1 C1 C2 O2 -177.7(3) . . . . ?
C4 C1 C2 O2 -59.8(4) . . . . ?
C5 C1 C2 O2 64.7(4) . . . . ?
N1 C1 C2 N2 3.4(2) . . . . ?
C4 C1 C2 N2 121.3(2) . . . . ?
C5 C1 C2 N2 -114.2(2) . . . . ?
C1 N1 C3 O1 179.84(18) . . . . ?
C1 N1 C3 N2 -0.1(2) . . . . ?
C2 N2 C3 O1 -177.36(17) . . . . ?
C2 N2 C3 N1 2.6(2) . . . . ?

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_aa_a
_database_code_depnum_ccdc_archive 'CCDC 1981078'
loop_
_audit_author_name
_audit_author_address
'Wang Zhang Yuan'
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2020-01-31 deposited with the CCDC.	2020-05-19 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 H4 N2 O2'
_chemical_formula_sum            'C3 H4 N2 O2'
_chemical_formula_weight         100.08

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      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                   9.3446(15)
_cell_length_b                   12.244(2)
_cell_length_c                   7.3458(13)
_cell_angle_alpha                90
_cell_angle_beta                 105.194(7)
_cell_angle_gamma                90
_cell_volume                     811.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5020
_cell_measurement_theta_min      6.09
_cell_measurement_theta_max      68.36

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   0.6003
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.210
_shelx_estimated_absorpt_T_min   0.760
_shelx_estimated_absorpt_T_max   0.794
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4803
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         6.094
_diffrn_reflns_theta_max         68.367
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             737
_reflns_number_gt                701
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0845P)²+1.3640P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         737
_refine_ls_number_parameters     64
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1665
_refine_ls_wR_factor_gt          0.1652
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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 -2.8520(2) -0.41781(16) -1.8859(3) 0.0555(7) Uani 1 1 d . . . . .
O2 O -2.5250(2) -0.65402(16) -1.5149(3) 0.0557(7) Uani 1 1 d . . . . .
N1 N -2.6639(2) -0.51558(17) -1.6862(3) 0.0419(6) Uani 1 1 d . . . . .
H1 H -2.606390 -0.461782 -1.641236 0.050 Uiso 1 1 d R U . . .
N2 N -2.8513(2) -0.6073(2) -1.8671(4) 0.0528(7) Uani 1 1 d . . . . .
H2A H -2.931117 -0.622325 -1.952768 0.063 Uiso 1 1 d R U . . .
C1 C -2.7548(3) -0.6879(2) -1.7514(4) 0.0459(7) Uani 1 1 d . . . . .
H1A H -2.717613 -0.739135 -1.828857 0.055 Uiso 1 1 calc R U . . .
H1B H -2.806267 -0.727976 -1.673859 0.055 Uiso 1 1 calc R U . . .
C2 C -2.7979(3) -0.5047(2) -1.8210(4) 0.0410(7) Uani 1 1 d . . . . .
C3 C -2.6332(3) -0.6215(2) -1.6341(4) 0.0416(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.220(3) . ?
O2 C3 1.218(3) . ?
N1 C3 1.362(3) . ?
N1 C2 1.384(3) . ?
N1 H1 0.8595 . ?
N2 C2 1.361(3) . ?
N2 C1 1.452(4) . ?
N2 H2A 0.8603 . ?
C1 C3 1.477(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

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
C3 N1 C2 112.1(2) . . ?
C3 N1 H1 123.9 . . ?
C2 N1 H1 123.9 . . ?
C2 N2 C1 110.5(2) . . ?
C2 N2 H2A 124.8 . . ?
C1 N2 H2A 124.7 . . ?
N2 C1 C3 103.4(2) . . ?
N2 C1 H1A 111.1 . . ?
C3 C1 H1A 111.1 . . ?
N2 C1 H1B 111.1 . . ?
C3 C1 H1B 111.1 . . ?
H1A C1 H1B 109.0 . . ?
O1 C2 N2 128.3(2) . . ?
O1 C2 N1 124.6(2) . . ?
N2 C2 N1 107.1(2) . . ?
O2 C3 N1 126.0(2) . . ?
O2 C3 C1 127.3(2) . . ?
N1 C3 C1 106.7(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
C2 N2 C1 C3 -1.9(3) . . . . ?
C1 N2 C2 O1 -178.2(3) . . . . ?
C1 N2 C2 N1 3.6(3) . . . . ?
C3 N1 C2 O1 177.6(3) . . . . ?
C3 N1 C2 N2 -4.1(3) . . . . ?
C2 N1 C3 O2 -178.0(3) . . . . ?
C2 N1 C3 C1 2.8(3) . . . . ?
N2 C1 C3 O2 -179.7(3) . . . . ?
N2 C1 C3 N1 -0.5(3) . . . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.053

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

data_aa_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1981077'
loop_
_audit_author_name
_audit_author_address
'Wang Zhang Yuan'
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2020-01-31 deposited with the CCDC.	2020-05-19 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         'C8 H10 N4 O4'
_chemical_formula_sum            'C8 H10 N4 O4'
_chemical_formula_weight         226.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   5.8982(5)
_cell_length_b                   12.4995(11)
_cell_length_c                   14.3372(10)
_cell_angle_alpha                90
_cell_angle_beta                 114.292(3)
_cell_angle_gamma                90
_cell_volume                     963.42(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6448
_cell_measurement_theta_min      3.38
_cell_measurement_theta_max      68.31

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   0.5606
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.094
_shelx_estimated_absorpt_T_min   0.779
_shelx_estimated_absorpt_T_max   0.811
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6844
_diffrn_reflns_av_unetI/netI     0.0762
_diffrn_reflns_av_R_equivalents  0.0997
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.896
_diffrn_reflns_theta_max         66.538
_diffrn_reflns_theta_full        66.538
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             1644
_reflns_number_gt                1356
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.115(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1644
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1020
_refine_ls_R_factor_gt           0.0811
_refine_ls_wR_factor_ref         0.2781
_refine_ls_wR_factor_gt          0.2448
_refine_ls_goodness_of_fit_ref   2.107
_refine_ls_restrained_S_all      2.107
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.005

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 -0.6394(3) 0.5599(2) -0.63514(16) 0.0588(8) Uani 1 1 d . . . . .
O2 O -0.9463(5) 0.6291(2) -0.39641(17) 0.0701(9) Uani 1 1 d . . . . .
O3 O -0.9159(4) 0.60677(16) -0.90674(17) 0.0561(8) Uani 1 1 d . . . . .
O4 O -1.4674(5) 0.3473(2) -0.9121(2) 0.0772(9) Uani 1 1 d . . . . .
N1 N -0.9818(4) 0.65616(19) -0.64483(15) 0.0468(8) Uani 1 1 d . . . . .
N2 N -1.1574(4) 0.5878(2) -0.81541(16) 0.0459(8) Uani 1 1 d . . . . .
N3 N -0.7372(4) 0.5868(2) -0.49600(16) 0.0522(8) Uani 1 1 d . . . . .
H3 H -0.612183 0.554136 -0.450583 0.063 Uiso 1 1 d R U . . .
N4 N -1.1783(4) 0.46206(19) -0.92614(18) 0.0533(8) Uani 1 1 d . . . . .
H4 H -1.147076 0.427777 -0.971558 0.064 Uiso 1 1 d R U . . .
C1 C -0.7734(4) 0.5981(2) -0.5972(2) 0.0456(9) Uani 1 1 d . . . . .
C3 C -0.9228(5) 0.6325(2) -0.4771(2) 0.0519(9) Uani 1 1 d . . . . .
C4 C -1.0948(5) 0.6832(2) -0.57560(19) 0.0486(9) Uani 1 1 d . . . . .
H4A H -1.261201 0.653756 -0.598949 0.058 Uiso 1 1 calc R U . . .
H4B H -1.102522 0.760110 -0.568330 0.058 Uiso 1 1 calc R U . . .
C5 C -1.0754(4) 0.6835(2) -0.75283(18) 0.0457(9) Uani 1 1 d . . . . .
H5 H -0.938491 0.715227 -0.765348 0.055 Uiso 1 1 calc R U . . .
C6 C -1.2834(6) 0.7656(3) -0.7819(3) 0.0618(10) Uani 1 1 d . . . . .
H6A H -1.420232 0.736046 -0.770625 0.093 Uiso 1 1 calc R U . . .
H6B H -1.337901 0.784044 -0.852877 0.093 Uiso 1 1 calc R U . . .
H6C H -1.223595 0.828579 -0.740735 0.093 Uiso 1 1 calc R U . . .
C7 C -1.3323(5) 0.5093(2) -0.8087(2) 0.0507(9) Uani 1 1 d . . . . .
H7A H -1.494744 0.540809 -0.825572 0.061 Uiso 1 1 calc R U . . .
H7B H -1.272551 0.477877 -0.740893 0.061 Uiso 1 1 calc R U . . .
C8 C -1.3405(5) 0.4276(3) -0.8876(2) 0.0530(9) Uani 1 1 d . . . . .
C10 C -1.0685(5) 0.5585(2) -0.8840(2) 0.0458(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.226(3) . ?
O2 C3 1.221(4) . ?
O3 C10 1.234(3) . ?
O4 C8 1.214(4) . ?
N1 C1 1.347(3) . ?
N1 C4 1.445(3) . ?
N1 C5 1.455(3) . ?
N2 C10 1.341(3) . ?
N2 C7 1.455(3) . ?
N2 C5 1.454(4) . ?
N3 C3 1.358(4) . ?
N3 C1 1.384(4) . ?
N3 H3 0.8601 . ?
N4 C8 1.356(4) . ?
N4 C10 1.384(4) . ?
N4 H4 0.8605 . ?
C3 C4 1.499(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.520(4) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.510(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

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
C1 N1 C4 111.1(2) . . ?
C1 N1 C5 122.3(2) . . ?
C4 N1 C5 126.6(2) . . ?
C10 N2 C7 111.5(2) . . ?
C10 N2 C5 123.1(2) . . ?
C7 N2 C5 125.4(2) . . ?
C3 N3 C1 112.2(2) . . ?
C3 N3 H3 124.0 . . ?
C1 N3 H3 123.8 . . ?
C8 N4 C10 112.4(3) . . ?
C8 N4 H4 123.8 . . ?
C10 N4 H4 123.8 . . ?
O1 C1 N1 127.3(3) . . ?
O1 C1 N3 125.2(2) . . ?
N1 C1 N3 107.6(2) . . ?
O2 C3 N3 126.2(3) . . ?
O2 C3 C4 127.7(3) . . ?
N3 C3 C4 106.1(2) . . ?
N1 C4 C3 103.0(2) . . ?
N1 C4 H4A 111.2 . . ?
C3 C4 H4A 111.2 . . ?
N1 C4 H4B 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
N1 C5 N2 110.3(2) . . ?
N1 C5 C6 111.2(2) . . ?
N2 C5 C6 111.1(2) . . ?
N1 C5 H5 108.0 . . ?
N2 C5 H5 108.0 . . ?
C6 C5 H5 108.0 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 C8 102.2(2) . . ?
N2 C7 H7A 111.3 . . ?
C8 C7 H7A 111.3 . . ?
N2 C7 H7B 111.3 . . ?
C8 C7 H7B 111.3 . . ?
H7A C7 H7B 109.2 . . ?
O4 C8 N4 126.8(3) . . ?
O4 C8 C7 127.0(3) . . ?
N4 C8 C7 106.3(2) . . ?
O3 C10 N2 127.5(3) . . ?
O3 C10 N4 124.9(3) . . ?
N2 C10 N4 107.7(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
C4 N1 C1 O1 177.5(3) . . . . ?
C5 N1 C1 O1 -1.2(5) . . . . ?
C4 N1 C1 N3 -1.4(3) . . . . ?
C5 N1 C1 N3 179.9(2) . . . . ?
C3 N3 C1 O1 -176.4(3) . . . . ?
C3 N3 C1 N1 2.5(3) . . . . ?
C1 N3 C3 O2 175.3(3) . . . . ?
C1 N3 C3 C4 -2.5(3) . . . . ?
C1 N1 C4 C3 0.0(3) . . . . ?
C5 N1 C4 C3 178.6(3) . . . . ?
O2 C3 C4 N1 -176.3(3) . . . . ?
N3 C3 C4 N1 1.5(3) . . . . ?
C1 N1 C5 N2 66.7(3) . . . . ?
C4 N1 C5 N2 -111.8(3) . . . . ?
C1 N1 C5 C6 -169.6(3) . . . . ?
C4 N1 C5 C6 11.9(4) . . . . ?
C10 N2 C5 N1 -123.6(2) . . . . ?
C7 N2 C5 N1 52.9(3) . . . . ?
C10 N2 C5 C6 112.7(3) . . . . ?
C7 N2 C5 C6 -70.9(3) . . . . ?
C10 N2 C7 C8 -1.4(3) . . . . ?
C5 N2 C7 C8 -178.3(2) . . . . ?
C10 N4 C8 O4 178.1(3) . . . . ?
C10 N4 C8 C7 -1.6(3) . . . . ?
N2 C7 C8 O4 -178.0(3) . . . . ?
N2 C7 C8 N4 1.8(3) . . . . ?
C7 N2 C10 O3 -179.2(3) . . . . ?
C5 N2 C10 O3 -2.3(4) . . . . ?
C7 N2 C10 N4 0.6(3) . . . . ?
C5 N2 C10 N4 177.5(2) . . . . ?
C8 N4 C10 O3 -179.5(2) . . . . ?
C8 N4 C10 N2 0.7(3) . . . . ?

_refine_diff_density_max         0.416
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.103

####################################################################### 
# 
# 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_t_a
_database_code_depnum_ccdc_archive 'CCDC 1981079'
loop_
_audit_author_name
_audit_author_address
'Wang Zhang Yuan'
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2020-01-31 deposited with the CCDC.	2020-05-19 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         'C7 H8 N4 O4'
_chemical_formula_sum            'C7 H8 N4 O4'
_chemical_formula_weight         212.17

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      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                   9.597(3)
_cell_length_b                   17.769(5)
_cell_length_c                   11.340(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.24(4)
_cell_angle_gamma                90
_cell_volume                     1763.2(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9847
_cell_measurement_theta_min      4.28
_cell_measurement_theta_max      68.31

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   0.5805
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.154
_shelx_estimated_absorpt_T_min   0.769
_shelx_estimated_absorpt_T_max   0.802
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22647
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.948
_diffrn_reflns_theta_max         68.395
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3218
_reflns_number_gt                2896
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1615P)²+6.3706P] 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_number_reflns         3218
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0922
_refine_ls_wR_factor_ref         0.3149
_refine_ls_wR_factor_gt          0.3125
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.3037(6) 0.8430(3) 0.7139(5) 0.0468(12) Uani 1 1 d . . . . .
O1 O 0.3402(6) 0.8915(3) 0.6588(4) 0.0742(14) Uani 1 1 d . . . . .
N1 N 0.1986(5) 0.7378(2) 0.7669(4) 0.0394(9) Uani 1 1 d . . . . .
O2 O 0.3191(4) 0.7529(2) 0.9884(3) 0.0505(9) Uani 1 1 d . . . . .
C2 C 0.2003(6) 0.7763(3) 0.6542(5) 0.0473(12) Uani 1 1 d . . . . .
H2A H 0.098527 0.792530 0.596336 0.057 Uiso 1 1 calc R U . . .
H2B H 0.241786 0.744333 0.607199 0.057 Uiso 1 1 calc R U . . .
N2 N 0.2034(5) 0.6027(2) 0.7525(4) 0.0397(9) Uani 1 1 d . . . . .
O3 O 0.0837(5) 0.5842(2) 0.5313(3) 0.0589(11) Uani 1 1 d . . . . .
C3 C 0.2905(5) 0.7727(2) 0.8779(4) 0.0369(10) Uani 1 1 d . . . . .
N3 N 0.3482(5) 0.8365(2) 0.8442(4) 0.0423(10) Uani 1 1 d . . . . .
H3 H 0.405935 0.868566 0.899397 0.051 Uiso 1 1 calc R U . . .
N6 N 0.2150(5) 0.4267(2) 0.2550(4) 0.0420(9) Uani 1 1 d . . . . .
O6 O 0.1222(5) 0.5848(2) 0.0245(3) 0.0537(10) Uani 1 1 d . . . . .
C6 C 0.3853(6) 0.5102(3) 0.7910(5) 0.0489(12) Uani 1 1 d . . . . .
C5 C 0.3327(6) 0.5700(3) 0.8575(5) 0.0488(12) Uani 1 1 d . . . . .
H5A H 0.302563 0.548216 0.921986 0.059 Uiso 1 1 calc R U . . .
H5B H 0.412075 0.607086 0.898587 0.059 Uiso 1 1 calc R U . . .
N5 N 0.2035(5) 0.5625(2) 0.2425(4) 0.0432(10) Uani 1 1 d . . . . .
O5 O 0.4269(5) 0.7207(2) 0.3782(4) 0.0615(11) Uani 1 1 d . . . . .
N4 N 0.2897(5) 0.5134(2) 0.6647(4) 0.0464(10) Uani 1 1 d . . . . .
H4 H 0.295697 0.484118 0.606601 0.056 Uiso 1 1 calc R U . . .
O4 O 0.4912(5) 0.4670(3) 0.8387(5) 0.0760(14) Uani 1 1 d . . . . .
C4 C 0.1201(5) 0.6681(2) 0.7636(5) 0.0381(10) Uani 1 1 d . . . . .
H4A H 0.020964 0.669140 0.690877 0.046 Uiso 1 1 calc R U . . .
H4B H 0.103028 0.663928 0.841964 0.046 Uiso 1 1 calc R U . . .
O7 O 0.3077(6) 0.4196(2) 0.4767(4) 0.0655(12) Uani 1 1 d . . . . .
N7 N 0.2798(5) 0.6667(2) 0.1825(4) 0.0463(10) Uani 1 1 d . . . . .
H7 H 0.289905 0.700628 0.132515 0.056 Uiso 1 1 calc R U . . .
C7 C 0.1807(6) 0.5694(3) 0.6396(4) 0.0399(10) Uani 1 1 d . . . . .
N8 N 0.3882(5) 0.3401(2) 0.3572(4) 0.0482(10) Uani 1 1 d . . . . .
H8 H 0.448216 0.312232 0.419361 0.058 Uiso 1 1 calc R U . . .
C8 C 0.3456(6) 0.6704(3) 0.3125(5) 0.0443(11) Uani 1 1 d . . . . .
O8 O 0.4308(6) 0.2880(3) 0.1887(5) 0.0754(14) Uani 1 1 d . . . . .
C9 C 0.2989(7) 0.6001(3) 0.3606(5) 0.0493(12) Uani 1 1 d . . . . .
H9A H 0.387104 0.569622 0.411548 0.059 Uiso 1 1 calc R U . . .
H9B H 0.242481 0.611897 0.412215 0.059 Uiso 1 1 calc R U . . .
C10 C 0.1932(6) 0.6011(3) 0.1381(5) 0.0411(11) Uani 1 1 d . . . . .
C11 C 0.1213(5) 0.4936(3) 0.2365(5) 0.0429(11) Uani 1 1 d . . . . .
H11A H 0.035043 0.490552 0.152996 0.051 Uiso 1 1 calc R U . . .
H11B H 0.081384 0.494899 0.302400 0.051 Uiso 1 1 calc R U . . .
C12 C 0.3019(6) 0.3982(3) 0.3732(5) 0.0411(11) Uani 1 1 d . . . . .
C13 C 0.3671(6) 0.3319(3) 0.2311(6) 0.0502(13) Uani 1 1 d . . . . .
C14 C 0.2486(6) 0.3904(3) 0.1545(5) 0.0495(12) Uani 1 1 d . . . . .
H14A H 0.290094 0.425959 0.112451 0.059 Uiso 1 1 calc R U . . .
H14B H 0.158192 0.366952 0.089946 0.059 Uiso 1 1 calc R 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 O1 1.198(6) . ?
C1 N3 1.364(6) . ?
C1 C2 1.515(7) . ?
N1 C3 1.355(6) . ?
N1 C4 1.442(6) . ?
N1 C2 1.455(6) . ?
O2 C3 1.219(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
N2 C7 1.344(6) . ?
N2 C5 1.443(6) . ?
N2 C4 1.445(6) . ?
O3 C7 1.227(6) . ?
C3 N3 1.382(6) . ?
N3 H3 0.8600 . ?
N6 C12 1.352(6) . ?
N6 C11 1.453(6) . ?
N6 C14 1.456(6) . ?
O6 C10 1.219(6) . ?
C6 O4 1.210(7) . ?
C6 N4 1.348(7) . ?
C6 C5 1.504(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
N5 C10 1.337(6) . ?
N5 C9 1.439(6) . ?
N5 C11 1.443(6) . ?
O5 C8 1.218(6) . ?
N4 C7 1.387(6) . ?
N4 H4 0.8600 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
O7 C12 1.213(6) . ?
N7 C8 1.346(7) . ?
N7 C10 1.399(6) . ?
N7 H7 0.8600 . ?
N8 C13 1.367(7) . ?
N8 C12 1.382(6) . ?
N8 H8 0.8600 . ?
C8 C9 1.504(7) . ?
O8 C13 1.205(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 C14 1.523(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?

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 N3 126.7(5) . . ?
O1 C1 C2 127.4(5) . . ?
N3 C1 C2 105.9(4) . . ?
C3 N1 C4 123.4(4) . . ?
C3 N1 C2 111.3(4) . . ?
C4 N1 C2 125.1(4) . . ?
N1 C2 C1 102.5(4) . . ?
N1 C2 H2A 111.3 . . ?
C1 C2 H2A 111.3 . . ?
N1 C2 H2B 111.3 . . ?
C1 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
C7 N2 C5 110.9(4) . . ?
C7 N2 C4 123.9(4) . . ?
C5 N2 C4 124.9(4) . . ?
O2 C3 N1 127.5(4) . . ?
O2 C3 N3 125.1(4) . . ?
N1 C3 N3 107.4(4) . . ?
C1 N3 C3 112.8(4) . . ?
C1 N3 H3 123.6 . . ?
C3 N3 H3 123.6 . . ?
C12 N6 C11 122.9(4) . . ?
C12 N6 C14 111.4(4) . . ?
C11 N6 C14 124.9(4) . . ?
O4 C6 N4 125.5(5) . . ?
O4 C6 C5 128.1(5) . . ?
N4 C6 C5 106.3(4) . . ?
N2 C5 C6 102.9(4) . . ?
N2 C5 H5A 111.2 . . ?
C6 C5 H5A 111.2 . . ?
N2 C5 H5B 111.2 . . ?
C6 C5 H5B 111.2 . . ?
H5A C5 H5B 109.1 . . ?
C10 N5 C9 111.9(4) . . ?
C10 N5 C11 123.6(4) . . ?
C9 N5 C11 124.4(4) . . ?
C6 N4 C7 112.0(4) . . ?
C6 N4 H4 124.0 . . ?
C7 N4 H4 124.0 . . ?
N1 C4 N2 113.0(4) . . ?
N1 C4 H4A 109.0 . . ?
N2 C4 H4A 109.0 . . ?
N1 C4 H4B 109.0 . . ?
N2 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C8 N7 C10 112.2(4) . . ?
C8 N7 H7 123.9 . . ?
C10 N7 H7 123.9 . . ?
O3 C7 N2 128.2(4) . . ?
O3 C7 N4 123.9(4) . . ?
N2 C7 N4 107.9(4) . . ?
C13 N8 C12 112.2(4) . . ?
C13 N8 H8 123.9 . . ?
C12 N8 H8 123.9 . . ?
O5 C8 N7 126.9(5) . . ?
O5 C8 C9 126.8(5) . . ?
N7 C8 C9 106.3(4) . . ?
N5 C9 C8 102.6(4) . . ?
N5 C9 H9A 111.2 . . ?
C8 C9 H9A 111.2 . . ?
N5 C9 H9B 111.2 . . ?
C8 C9 H9B 111.2 . . ?
H9A C9 H9B 109.2 . . ?
O6 C10 N5 128.3(5) . . ?
O6 C10 N7 124.8(4) . . ?
N5 C10 N7 106.9(4) . . ?
N5 C11 N6 113.2(4) . . ?
N5 C11 H11A 108.9 . . ?
N6 C11 H11A 108.9 . . ?
N5 C11 H11B 108.9 . . ?
N6 C11 H11B 108.9 . . ?
H11A C11 H11B 107.8 . . ?
O7 C12 N6 127.3(5) . . ?
O7 C12 N8 124.7(5) . . ?
N6 C12 N8 108.0(4) . . ?
O8 C13 N8 127.2(6) . . ?
O8 C13 C14 126.6(5) . . ?
N8 C13 C14 106.2(4) . . ?
N6 C14 C13 102.1(4) . . ?
N6 C14 H14A 111.3 . . ?
C13 C14 H14A 111.3 . . ?
N6 C14 H14B 111.4 . . ?
C13 C14 H14B 111.4 . . ?
H14A C14 H14B 109.2 . . ?

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
C3 N1 C2 C1 -2.3(6) . . . . ?
C4 N1 C2 C1 -177.6(4) . . . . ?
O1 C1 C2 N1 179.9(6) . . . . ?
N3 C1 C2 N1 0.4(6) . . . . ?
C4 N1 C3 O2 -1.3(8) . . . . ?
C2 N1 C3 O2 -176.6(5) . . . . ?
C4 N1 C3 N3 178.7(4) . . . . ?
C2 N1 C3 N3 3.4(6) . . . . ?
O1 C1 N3 C3 -177.9(6) . . . . ?
C2 C1 N3 C3 1.7(6) . . . . ?
O2 C3 N3 C1 176.8(5) . . . . ?
N1 C3 N3 C1 -3.2(6) . . . . ?
C7 N2 C5 C6 -0.6(6) . . . . ?
C4 N2 C5 C6 -173.9(4) . . . . ?
O4 C6 C5 N2 180.0(6) . . . . ?
N4 C6 C5 N2 -0.2(6) . . . . ?
O4 C6 N4 C7 -179.3(6) . . . . ?
C5 C6 N4 C7 0.9(6) . . . . ?
C3 N1 C4 N2 -94.6(5) . . . . ?
C2 N1 C4 N2 80.1(6) . . . . ?
C7 N2 C4 N1 -94.8(5) . . . . ?
C5 N2 C4 N1 77.7(6) . . . . ?
C5 N2 C7 O3 -178.3(5) . . . . ?
C4 N2 C7 O3 -4.9(8) . . . . ?
C5 N2 C7 N4 1.1(6) . . . . ?
C4 N2 C7 N4 174.5(4) . . . . ?
C6 N4 C7 O3 178.2(5) . . . . ?
C6 N4 C7 N2 -1.3(6) . . . . ?
C10 N7 C8 O5 -179.9(5) . . . . ?
C10 N7 C8 C9 0.2(6) . . . . ?
C10 N5 C9 C8 0.9(6) . . . . ?
C11 N5 C9 C8 -175.8(4) . . . . ?
O5 C8 C9 N5 179.4(5) . . . . ?
N7 C8 C9 N5 -0.6(6) . . . . ?
C9 N5 C10 O6 179.8(5) . . . . ?
C11 N5 C10 O6 -3.4(8) . . . . ?
C9 N5 C10 N7 -0.9(6) . . . . ?
C11 N5 C10 N7 175.9(4) . . . . ?
C8 N7 C10 O6 179.8(5) . . . . ?
C8 N7 C10 N5 0.4(6) . . . . ?
C10 N5 C11 N6 101.0(6) . . . . ?
C9 N5 C11 N6 -82.6(6) . . . . ?
C12 N6 C11 N5 86.6(6) . . . . ?
C14 N6 C11 N5 -82.0(6) . . . . ?
C11 N6 C12 O7 5.2(8) . . . . ?
C14 N6 C12 O7 175.1(5) . . . . ?
C11 N6 C12 N8 -173.6(4) . . . . ?
C14 N6 C12 N8 -3.7(6) . . . . ?
C13 N8 C12 O7 -175.3(5) . . . . ?
C13 N8 C12 N6 3.5(6) . . . . ?
C12 N8 C13 O8 177.1(6) . . . . ?
C12 N8 C13 C14 -1.9(6) . . . . ?
C12 N6 C14 C13 2.4(6) . . . . ?
C11 N6 C14 C13 172.1(4) . . . . ?
O8 C13 C14 N6 -179.3(6) . . . . ?
N8 C13 C14 N6 -0.3(6) . . . . ?

_refine_diff_density_max         0.587
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.105

