# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2171804'
loop_
_audit_author_name
_audit_author_address
'Jinhao Zhang'
;SWUST
China
;
_audit_update_record             
;
2022-05-10 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT340_1_a                 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.012 Ang.  
RESPONSE: This is caused by the poor quality of the sample.
;
# 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         ?
_chemical_formula_sum            'C3 H5 N7 O2'
_chemical_formula_weight         171.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   8.2815(3)
_cell_length_b                   16.56970(10)
_cell_length_c                   4.7742(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     655.13(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    302
_cell_measurement_theta_min      3.48
_cell_measurement_theta_max      20.27

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.146
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2739
_diffrn_reflns_av_unetI/netI     0.1086
_diffrn_reflns_av_R_equivalents  0.0941
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.458
_diffrn_reflns_theta_max         25.005
_diffrn_reflns_theta_full        25.005
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_point_group_measured_fraction_full 0.871
_reflns_number_total             1009
_reflns_number_gt                622
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.550
_reflns_Friedel_fraction_max     0.710
_reflns_Friedel_fraction_full    0.710

_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)+(0.0611P)²+0.1297P] 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_abs_structure_details 
;
 Flack x determined using 183 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1009
_refine_ls_number_parameters     109
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1267
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1519
_refine_ls_wR_factor_gt          0.1222
_refine_ls_goodness_of_fit_ref   1.052
_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 0.3427(9) 0.7697(5) 0.456(2) 0.025(2) Uani 1 1 d . . . . .
C2 C 0.3045(10) 0.6872(5) 0.3801(19) 0.027(2) Uani 1 1 d . . . . .
C3 C 0.2029(10) 0.5870(5) 0.159(2) 0.028(2) Uani 1 1 d . . . . .
H3 H 0.1455 0.5550 0.0340 0.034 Uiso 1 1 calc R U . . .
N1 N 0.4427(8) 0.7920(4) 0.6621(15) 0.0252(17) Uani 1 1 d . . . . .
N2 N 0.4495(9) 0.8732(4) 0.6679(18) 0.0347(18) Uani 1 1 d . . . . .
N3 N 0.3540(9) 0.8981(4) 0.4664(17) 0.039(2) Uani 1 1 d . . . . .
N4 N 0.2865(8) 0.8352(4) 0.3362(16) 0.0328(19) Uani 1 1 d . . . . .
N5 N 0.3653(8) 0.6229(4) 0.5046(15) 0.0302(18) Uani 1 1 d . . . . .
N6 N 0.2036(8) 0.6671(4) 0.1669(15) 0.0304(19) Uani 1 1 d . . . . .
H6 H 0.1511 0.6995 0.0594 0.036 Uiso 1 1 calc R U . . .
N7 N 0.2982(8) 0.5608(4) 0.3609(17) 0.0272(17) Uani 1 1 d . . . . .
H7 H 0.3156 0.5107 0.3969 0.033 Uiso 1 1 calc R U . . .
O1 O 0.5268(7) 0.7471(3) 0.8369(15) 0.0398(16) Uani 1 1 d . . . . .
O2 O 0.4154(7) 0.4199(3) 0.4615(13) 0.0353(17) Uani 1 1 d . . . . .
H2A H 0.3690 0.3845 0.5624 0.053 Uiso 1 1 d R U . . .
H2B H 0.5134 0.4189 0.5142 0.053 Uiso 1 1 d 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 N4 1.313(10) . ?
C1 N1 1.337(11) . ?
C1 C2 1.450(11) . ?
C2 N5 1.319(9) . ?
C2 N6 1.359(11) . ?
C3 N7 1.318(11) . ?
C3 N6 1.329(9) . ?
C3 H3 0.9300 . ?
N1 O1 1.317(8) . ?
N1 N2 1.347(9) . ?
N2 N3 1.312(10) . ?
N3 N4 1.335(9) . ?
N5 N7 1.356(9) . ?
N6 H6 0.8600 . ?
N7 H7 0.8600 . ?
O2 H2A 0.8501 . ?
O2 H2B 0.8500 . ?

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
N4 C1 N1 108.2(7) . . ?
N4 C1 C2 126.3(8) . . ?
N1 C1 C2 125.5(8) . . ?
N5 C2 N6 112.0(7) . . ?
N5 C2 C1 124.4(8) . . ?
N6 C2 C1 123.6(7) . . ?
N7 C3 N6 107.8(8) . . ?
N7 C3 H3 126.1 . . ?
N6 C3 H3 126.1 . . ?
O1 N1 C1 129.6(7) . . ?
O1 N1 N2 121.9(7) . . ?
C1 N1 N2 108.5(7) . . ?
N3 N2 N1 105.9(7) . . ?
N2 N3 N4 110.4(7) . . ?
C1 N4 N3 107.1(7) . . ?
C2 N5 N7 103.2(6) . . ?
C3 N6 C2 105.5(7) . . ?
C3 N6 H6 127.2 . . ?
C2 N6 H6 127.2 . . ?
C3 N7 N5 111.5(7) . . ?
C3 N7 H7 124.3 . . ?
N5 N7 H7 124.3 . . ?
H2A O2 H2B 104.5 . . ?

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
N4 C1 C2 N5 179.1(9) . . . . ?
N1 C1 C2 N5 -0.4(12) . . . . ?
N4 C1 C2 N6 0.4(12) . . . . ?
N1 C1 C2 N6 -179.1(9) . . . . ?
N4 C1 N1 O1 -179.7(7) . . . . ?
C2 C1 N1 O1 0.0(13) . . . . ?
N4 C1 N1 N2 -0.4(9) . . . . ?
C2 C1 N1 N2 179.2(7) . . . . ?
O1 N1 N2 N3 179.2(6) . . . . ?
C1 N1 N2 N3 0.0(9) . . . . ?
N1 N2 N3 N4 0.5(9) . . . . ?
N1 C1 N4 N3 0.7(9) . . . . ?
C2 C1 N4 N3 -178.9(7) . . . . ?
N2 N3 N4 C1 -0.8(10) . . . . ?
N6 C2 N5 N7 -0.1(9) . . . . ?
C1 C2 N5 N7 -178.9(7) . . . . ?
N7 C3 N6 C2 0.5(9) . . . . ?
N5 C2 N6 C3 -0.3(9) . . . . ?
C1 C2 N6 C3 178.6(7) . . . . ?
N6 C3 N7 N5 -0.6(9) . . . . ?
C2 N5 N7 C3 0.4(9) . . . . ?

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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 2189511'
loop_
_audit_author_name
_audit_author_address
'Jinhao Zhang'
;SWUST
China
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2023-04-12 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         ?
_chemical_formula_sum            'C3 H6 N8 O'
_chemical_formula_weight         170.16

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           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   3.6672(3)
_cell_length_b                   24.648(2)
_cell_length_c                   7.3252(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.280(3)
_cell_angle_gamma                90
_cell_volume                     655.21(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1569
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      25.39

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.139
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3026
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.306
_diffrn_reflns_theta_max         27.807
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.762
_diffrn_reflns_point_group_measured_fraction_full 0.874
_reflns_number_total             1192
_reflns_number_gt                1039
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_max     0.618
_reflns_Friedel_fraction_full    0.764

_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)+(0.0499P)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 391 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1192
_refine_ls_number_parameters     121
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0881
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.056
_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 0.3182(8) 0.36763(12) 0.5723(4) 0.0246(7) Uani 1 1 d . . . . .
C2 C 0.4185(8) 0.33502(12) 0.4219(4) 0.0249(7) Uani 1 1 d . . . . .
C3 C 0.5782(10) 0.31112(13) 0.1722(5) 0.0330(9) Uani 1 1 d . . . . .
H3 H 0.6500 0.3106 0.0555 0.040 Uiso 1 1 calc R U . . .
N1 N 0.3344(7) 0.42160(10) 0.5865(4) 0.0279(7) Uani 1 1 d . . . . .
N2 N 0.2248(8) 0.43586(12) 0.7478(4) 0.0368(8) Uani 1 1 d . . . . .
N3 N 0.1460(9) 0.39079(11) 0.8278(4) 0.0409(8) Uani 1 1 d . . . . .
N4 N 0.1991(8) 0.34766(11) 0.7230(4) 0.0319(7) Uani 1 1 d . . . . .
N5 N 0.5050(8) 0.35555(11) 0.2613(4) 0.0331(7) Uani 1 1 d . . . . .
N6 N 0.4312(8) 0.28187(11) 0.4347(4) 0.0313(7) Uani 1 1 d . . . . .
N7 N 0.5359(8) 0.26807(11) 0.2707(4) 0.0332(7) Uani 1 1 d . . . . .
H7 H 0.5698 0.2353 0.2363 0.040 Uiso 1 1 calc R U . . .
N8 N 0.8560(8) 0.54643(10) 0.6477(4) 0.0298(7) Uani 1 1 d D . . . .
H8D H 1.033(7) 0.5354(10) 0.735(3) 0.036 Uiso 1 1 d D U . . .
H8A H 0.731(7) 0.5166(9) 0.598(4) 0.036 Uiso 1 1 d D U . . .
H8B H 0.706(7) 0.5692(10) 0.687(4) 0.036 Uiso 1 1 d D U . . .
H8C H 0.963(8) 0.5618(11) 0.554(3) 0.036 Uiso 1 1 d D U . . .
O1 O 0.4296(7) 0.45808(8) 0.4725(3) 0.0383(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
C1 N1 1.335(4) . ?
C1 N4 1.338(4) . ?
C1 C2 1.453(4) . ?
C2 N6 1.314(4) . ?
C2 N5 1.360(4) . ?
C3 N7 1.305(4) . ?
C3 N5 1.322(4) . ?
C3 H3 0.9300 . ?
N1 O1 1.309(3) . ?
N1 N2 1.348(4) . ?
N2 N3 1.307(4) . ?
N3 N4 1.342(4) . ?
N6 N7 1.356(4) . ?
N7 H7 0.8600 . ?
N8 H8D 0.89(2) . ?
N8 H8A 0.92(2) . ?
N8 H8B 0.87(2) . ?
N8 H8C 0.92(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N4 108.5(3) . . ?
N1 C1 C2 126.7(3) . . ?
N4 C1 C2 124.8(3) . . ?
N6 C2 N5 115.0(3) . . ?
N6 C2 C1 120.5(3) . . ?
N5 C2 C1 124.5(3) . . ?
N7 C3 N5 110.6(3) . . ?
N7 C3 H3 124.7 . . ?
N5 C3 H3 124.7 . . ?
O1 N1 C1 130.4(3) . . ?
O1 N1 N2 121.4(3) . . ?
C1 N1 N2 108.2(3) . . ?
N3 N2 N1 106.5(3) . . ?
N2 N3 N4 111.0(3) . . ?
C1 N4 N3 105.8(3) . . ?
C3 N5 C2 102.0(3) . . ?
C2 N6 N7 101.5(3) . . ?
C3 N7 N6 110.9(3) . . ?
C3 N7 H7 124.5 . . ?
N6 N7 H7 124.5 . . ?
H8D N8 H8A 108.4(17) . . ?
H8D N8 H8B 113(2) . . ?
H8A N8 H8B 110(2) . . ?
H8D N8 H8C 109(2) . . ?
H8A N8 H8C 106.0(18) . . ?
H8B N8 H8C 110.1(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N6 171.9(3) . . . . ?
N4 C1 C2 N6 -6.7(5) . . . . ?
N1 C1 C2 N5 -8.0(5) . . . . ?
N4 C1 C2 N5 173.3(3) . . . . ?
N4 C1 N1 O1 -179.0(3) . . . . ?
C2 C1 N1 O1 2.2(5) . . . . ?
N4 C1 N1 N2 0.1(3) . . . . ?
C2 C1 N1 N2 -178.8(3) . . . . ?
O1 N1 N2 N3 179.3(3) . . . . ?
C1 N1 N2 N3 0.2(3) . . . . ?
N1 N2 N3 N4 -0.3(4) . . . . ?
N1 C1 N4 N3 -0.3(3) . . . . ?
C2 C1 N4 N3 178.6(3) . . . . ?
N2 N3 N4 C1 0.4(4) . . . . ?
N7 C3 N5 C2 0.5(4) . . . . ?
N6 C2 N5 C3 -0.6(4) . . . . ?
C1 C2 N5 C3 179.3(3) . . . . ?
N5 C2 N6 N7 0.5(4) . . . . ?
C1 C2 N6 N7 -179.5(3) . . . . ?
N5 C3 N7 N6 -0.2(4) . . . . ?
C2 N6 N7 C3 -0.1(4) . . . . ?

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2189512'
loop_
_audit_author_name
_audit_author_address
'Jinhao Zhang'
;SWUST
China
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2023-04-12 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         ?
_chemical_formula_sum            'C0.86 H1.71 N2.29 O0.57'
_chemical_formula_weight         53.19

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                   12.7140(16)
_cell_length_b                   8.0602(10)
_cell_length_c                   7.0415(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.899(3)
_cell_angle_gamma                90
_cell_volume                     717.77(15)
_cell_formula_units_Z            14
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5950
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      25.00

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.145
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12358
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.997
_diffrn_reflns_theta_max         25.041
_diffrn_reflns_theta_full        25.041
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1262
_reflns_number_gt                1052
_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)+(0.0417P)²+0.2622P] 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         1262
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0913
_refine_ls_wR_factor_gt          0.0848
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_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 0.26993(13) 0.6332(2) 0.7692(2) 0.0248(4) Uani 1 1 d . . . . .
C2 C 0.33058(13) 0.4806(2) 0.7823(2) 0.0254(4) Uani 1 1 d . . . . .
N7 N 0.46112(12) 0.32530(19) 0.7890(2) 0.0357(4) Uani 1 1 d . . . . .
H7 H 0.5243 0.2880 0.7863 0.043 Uiso 1 1 calc R U . . .
N1 N 0.16663(11) 0.65144(17) 0.78162(19) 0.0235(4) Uani 1 1 d . . . . .
N2 N 0.14198(12) 0.81314(19) 0.7673(2) 0.0332(4) Uani 1 1 d . . . . .
N3 N 0.23019(12) 0.8910(2) 0.7457(2) 0.0377(4) Uani 1 1 d . . . . .
N4 N 0.31097(12) 0.78310(19) 0.7462(2) 0.0340(4) Uani 1 1 d . . . . .
N5 N 0.29241(11) 0.32664(19) 0.8123(2) 0.0323(4) Uani 1 1 d . . . . .
N6 N 0.43315(12) 0.48618(19) 0.7672(2) 0.0356(4) Uani 1 1 d . . . . .
C3 C 0.37823(14) 0.2333(2) 0.8151(3) 0.0342(5) Uani 1 1 d . . . . .
H3 H 0.3798 0.1190 0.8330 0.041 Uiso 1 1 calc R U . . .
O2 O 0.07487(10) 0.33371(15) 0.51144(17) 0.0364(4) Uani 1 1 d . . . . .
H2 H 0.0729 0.4094 0.5888 0.044 Uiso 1 1 calc R U . . .
O1 O 0.09377(9) 0.53757(15) 0.80452(16) 0.0271(3) Uani 1 1 d . . . . .
N8 N 0.10036(11) 0.18447(18) 0.6088(2) 0.0262(4) Uani 1 1 d . . . . .
H8A H 0.1559 0.2006 0.6946 0.039 Uiso 1 1 calc R U . . .
H8B H 0.1159 0.1073 0.5258 0.039 Uiso 1 1 calc R U . . .
H8C H 0.0454 0.1511 0.6677 0.039 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 N4 1.332(2) . ?
C1 N1 1.333(2) . ?
C1 C2 1.450(2) . ?
C2 N6 1.320(2) . ?
C2 N5 1.357(2) . ?
N7 C3 1.317(2) . ?
N7 N6 1.349(2) . ?
N7 H7 0.8600 . ?
N1 O1 1.3256(17) . ?
N1 N2 1.342(2) . ?
N2 N3 1.308(2) . ?
N3 N4 1.346(2) . ?
N5 C3 1.324(2) . ?
C3 H3 0.9300 . ?
O2 N8 1.4058(18) . ?
O2 H2 0.8200 . ?
N8 H8A 0.8900 . ?
N8 H8B 0.8900 . ?
N8 H8C 0.8900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 C1 N1 107.99(15) . . ?
N4 C1 C2 124.39(15) . . ?
N1 C1 C2 127.61(16) . . ?
N6 C2 N5 114.59(16) . . ?
N6 C2 C1 119.28(16) . . ?
N5 C2 C1 126.13(15) . . ?
C3 N7 N6 110.60(15) . . ?
C3 N7 H7 124.7 . . ?
N6 N7 H7 124.7 . . ?
O1 N1 C1 129.58(14) . . ?
O1 N1 N2 121.39(13) . . ?
C1 N1 N2 109.03(14) . . ?
N3 N2 N1 106.17(14) . . ?
N2 N3 N4 110.66(15) . . ?
C1 N4 N3 106.15(14) . . ?
C3 N5 C2 102.39(15) . . ?
C2 N6 N7 102.05(15) . . ?
N7 C3 N5 110.37(17) . . ?
N7 C3 H3 124.8 . . ?
N5 C3 H3 124.8 . . ?
N8 O2 H2 109.5 . . ?
O2 N8 H8A 109.5 . . ?
O2 N8 H8B 109.5 . . ?
H8A N8 H8B 109.5 . . ?
O2 N8 H8C 109.5 . . ?
H8A N8 H8C 109.5 . . ?
H8B N8 H8C 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
N4 C1 C2 N6 -1.4(3) . . . . ?
N1 C1 C2 N6 -179.79(17) . . . . ?
N4 C1 C2 N5 177.55(18) . . . . ?
N1 C1 C2 N5 -0.8(3) . . . . ?
N4 C1 N1 O1 179.84(15) . . . . ?
C2 C1 N1 O1 -1.6(3) . . . . ?
N4 C1 N1 N2 -0.26(19) . . . . ?
C2 C1 N1 N2 178.33(16) . . . . ?
O1 N1 N2 N3 -179.83(14) . . . . ?
C1 N1 N2 N3 0.26(19) . . . . ?
N1 N2 N3 N4 -0.16(19) . . . . ?
N1 C1 N4 N3 0.15(19) . . . . ?
C2 C1 N4 N3 -178.49(16) . . . . ?
N2 N3 N4 C1 0.0(2) . . . . ?
N6 C2 N5 C3 -0.1(2) . . . . ?
C1 C2 N5 C3 -179.07(17) . . . . ?
N5 C2 N6 N7 0.0(2) . . . . ?
C1 C2 N6 N7 179.10(16) . . . . ?
C3 N7 N6 C2 0.0(2) . . . . ?
N6 N7 C3 N5 -0.1(2) . . . . ?
C2 N5 C3 N7 0.1(2) . . . . ?

_refine_diff_density_max         0.164
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2189513'
loop_
_audit_author_name
_audit_author_address
'Jinhao Zhang'
;SWUST
China
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT112_1_a                 
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem         m        100 %Fit  
RESPONSE: This is caused by the pseudosymmetry of the structure.
;
_vrf_PLAT113_1_a                 
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group       Cmca Check 
RESPONSE: This is caused by the pseudosymmetry of the structure.
;
# 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         ?
_chemical_formula_sum            'C3 H7 N9 O'
_chemical_formula_weight         185.18

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                   12.9556(15)
_cell_length_b                   8.7565(10)
_cell_length_c                   6.4841(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.077(3)
_cell_angle_gamma                90
_cell_volume                     713.50(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4274
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      24.24

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.139
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13615
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.835
_diffrn_reflns_theta_max         25.194
_diffrn_reflns_theta_full        25.194
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             1269
_reflns_number_gt                996
_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)+(0.0481P)²+0.9725P] 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         1269
_refine_ls_number_parameters     125
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1412
_refine_ls_wR_factor_gt          0.1306
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_restrained_S_all      1.177
_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 0.2249(2) 0.3186(3) 0.3672(5) 0.0221(7) Uani 1 1 d . . . . .
C2 C 0.1691(2) 0.4638(3) 0.3411(5) 0.0237(7) Uani 1 1 d . . . . .
C3 C 0.1322(3) 0.6960(4) 0.3333(6) 0.0349(8) Uani 1 1 d . . . . .
H3 H 0.1360 0.8019 0.3410 0.042 Uiso 1 1 calc R U . . .
N1 N 0.33045(19) 0.2954(3) 0.4170(4) 0.0225(6) Uani 1 1 d . . . . .
N2 N 0.3498(2) 0.1448(3) 0.4274(4) 0.0283(6) Uani 1 1 d . . . . .
N3 N 0.2561(2) 0.0776(3) 0.3829(4) 0.0309(7) Uani 1 1 d . . . . .
N4 N 0.1779(2) 0.1826(3) 0.3454(4) 0.0276(7) Uani 1 1 d . . . . .
N5 N 0.0647(2) 0.4664(3) 0.2789(4) 0.0326(7) Uani 1 1 d . . . . .
N6 N 0.2157(2) 0.6027(3) 0.3791(5) 0.0332(7) Uani 1 1 d . . . . .
N7 N 0.0436(2) 0.6174(3) 0.2759(4) 0.0334(7) Uani 1 1 d . . . . .
H7 H -0.0191 0.6566 0.2411 0.040 Uiso 1 1 calc R U . . .
N8 N 0.5897(2) 0.1764(3) 0.3326(5) 0.0326(7) Uani 1 1 d D . . . .
H8B H 0.647(2) 0.136(4) 0.299(5) 0.039 Uiso 1 1 d D U . . .
H8A H 0.533(2) 0.139(4) 0.241(5) 0.039 Uiso 1 1 d D U . . .
N9 N 0.5830(2) 0.3356(3) 0.2795(4) 0.0309(7) Uani 1 1 d . . . . .
H9A H 0.5214 0.3729 0.2950 0.046 Uiso 1 1 calc R U . . .
H9B H 0.5869 0.3474 0.1453 0.046 Uiso 1 1 calc R U . . .
H9C H 0.6365 0.3854 0.3652 0.046 Uiso 1 1 calc R U . . .
O1 O 0.40815(15) 0.3973(2) 0.4549(3) 0.0287(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 N4 1.328(4) . ?
C1 N1 1.342(4) . ?
C1 C2 1.452(4) . ?
C2 N5 1.315(4) . ?
C2 N6 1.353(4) . ?
C3 N7 1.312(4) . ?
C3 N6 1.330(4) . ?
C3 H3 0.9300 . ?
N1 O1 1.323(3) . ?
N1 N2 1.341(3) . ?
N2 N3 1.316(4) . ?
N3 N4 1.345(4) . ?
N5 N7 1.349(4) . ?
N7 H7 0.8600 . ?
N8 N9 1.434(4) . ?
N8 H8B 0.896(19) . ?
N8 H8A 0.889(18) . ?
N9 H9A 0.8900 . ?
N9 H9B 0.8900 . ?
N9 H9C 0.8900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 C1 N1 107.7(2) . . ?
N4 C1 C2 124.8(3) . . ?
N1 C1 C2 127.5(3) . . ?
N5 C2 N6 114.8(3) . . ?
N5 C2 C1 119.8(3) . . ?
N6 C2 C1 125.4(3) . . ?
N7 C3 N6 110.4(3) . . ?
N7 C3 H3 124.8 . . ?
N6 C3 H3 124.8 . . ?
O1 N1 N2 122.0(2) . . ?
O1 N1 C1 128.9(2) . . ?
N2 N1 C1 109.1(2) . . ?
N3 N2 N1 106.1(2) . . ?
N2 N3 N4 110.3(2) . . ?
C1 N4 N3 106.8(2) . . ?
C2 N5 N7 102.2(3) . . ?
C3 N6 C2 102.1(3) . . ?
C3 N7 N5 110.5(3) . . ?
C3 N7 H7 124.8 . . ?
N5 N7 H7 124.8 . . ?
N9 N8 H8B 109(2) . . ?
N9 N8 H8A 102(2) . . ?
H8B N8 H8A 107(3) . . ?
N8 N9 H9A 109.5 . . ?
N8 N9 H9B 109.5 . . ?
H9A N9 H9B 109.5 . . ?
N8 N9 H9C 109.5 . . ?
H9A N9 H9C 109.5 . . ?
H9B N9 H9C 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
N4 C1 C2 N5 -4.4(5) . . . . ?
N1 C1 C2 N5 175.8(3) . . . . ?
N4 C1 C2 N6 174.5(3) . . . . ?
N1 C1 C2 N6 -5.3(5) . . . . ?
N4 C1 N1 O1 -179.5(3) . . . . ?
C2 C1 N1 O1 0.3(5) . . . . ?
N4 C1 N1 N2 -0.2(3) . . . . ?
C2 C1 N1 N2 179.5(3) . . . . ?
O1 N1 N2 N3 179.6(2) . . . . ?
C1 N1 N2 N3 0.3(3) . . . . ?
N1 N2 N3 N4 -0.2(3) . . . . ?
N1 C1 N4 N3 0.1(3) . . . . ?
C2 C1 N4 N3 -179.7(3) . . . . ?
N2 N3 N4 C1 0.1(3) . . . . ?
N6 C2 N5 N7 0.4(4) . . . . ?
C1 C2 N5 N7 179.4(3) . . . . ?
N7 C3 N6 C2 0.8(4) . . . . ?
N5 C2 N6 C3 -0.8(4) . . . . ?
C1 C2 N6 C3 -179.7(3) . . . . ?
N6 C3 N7 N5 -0.6(4) . . . . ?
C2 N5 N7 C3 0.1(4) . . . . ?

_refine_diff_density_max         0.315
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.068

