# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_YF021_a
_database_code_depnum_ccdc_archive 'CCDC 2005560'
loop_
_audit_author_name
_audit_author_address
'Feng Yang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-07-09 deposited with the CCDC.	2021-03-11 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         'C6 H5 Cl N4'
_chemical_formula_sum            'C6 H5 Cl N4'
_chemical_formula_weight         168.59

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'
Cl Cl 0.1484 0.1585 '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                   3.9124(3)
_cell_length_b                   15.4255(12)
_cell_length_c                   11.8549(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.293(3)
_cell_angle_gamma                90
_cell_volume                     714.27(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3393
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.56

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.464
_shelx_estimated_absorpt_T_min   0.921
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.622
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   twinabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source.type              microfocus
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2565
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.169
_diffrn_reflns_theta_max         27.564
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             2565
_reflns_number_gt                1993
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component 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)+(0.0540P)²+0.3099P] 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         2565
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1241
_refine_ls_wR_factor_gt          0.1137
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.4775(7) 0.21183(16) 0.3849(2) 0.0368(6) Uani 1 1 d . . . . .
C2 C 0.4583(7) 0.25421(16) 0.4869(2) 0.0370(6) Uani 1 1 d . . . . .
H2 H 0.549767 0.229530 0.553536 0.044 Uiso 1 1 calc R U . . .
C3 C 0.2998(7) 0.33416(16) 0.4874(2) 0.0357(6) Uani 1 1 d . . . . .
C4 C 0.2151(7) 0.31805(17) 0.2845(2) 0.0347(6) Uani 1 1 d . . . . .
C5 C 0.0658(7) 0.36974(19) 0.2008(2) 0.0432(7) Uani 1 1 d . . . . .
H5 H 0.047180 0.358339 0.123673 0.052 Uiso 1 1 calc R U . . .
C6 C -0.0499(7) 0.44174(19) 0.2552(2) 0.0449(7) Uani 1 1 d . . . . .
H6 H -0.164376 0.486969 0.217443 0.054 Uiso 1 1 calc R U . . .
Cl1 Cl 0.6649(2) 0.10915(5) 0.38830(7) 0.0554(3) Uani 1 1 d . . . . .
N1 N 0.3664(6) 0.23893(14) 0.28507(19) 0.0397(6) Uani 1 1 d . . . . .
N2 N 0.1823(5) 0.36425(13) 0.38377(17) 0.0338(5) Uani 1 1 d . . . . .
N3 N 0.0160(6) 0.44121(14) 0.36672(19) 0.0429(6) Uani 1 1 d . . . . .
N4 N 0.2495(7) 0.38187(15) 0.5774(2) 0.0565(7) Uani 1 1 d . . . . .
H4A H 0.144754 0.430745 0.570065 0.068 Uiso 1 1 calc R U . . .
H4B H 0.321406 0.364097 0.643267 0.068 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 N1 1.305(3) . ?
C1 C2 1.381(4) . ?
C1 Cl1 1.745(3) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C3 N4 1.320(3) . ?
C3 N2 1.368(3) . ?
C4 N1 1.356(3) . ?
C4 C5 1.377(4) . ?
C4 N2 1.388(3) . ?
C5 C6 1.374(4) . ?
C5 H5 0.9300 . ?
C6 N3 1.332(3) . ?
C6 H6 0.9300 . ?
N2 N3 1.363(3) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 127.6(2) . . ?
N1 C1 Cl1 115.4(2) . . ?
C2 C1 Cl1 116.9(2) . . ?
C3 C2 C1 118.3(2) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
N4 C3 N2 118.6(2) . . ?
N4 C3 C2 126.1(2) . . ?
N2 C3 C2 115.3(2) . . ?
N1 C4 C5 133.8(2) . . ?
N1 C4 N2 121.3(2) . . ?
C5 C4 N2 104.9(2) . . ?
C6 C5 C4 105.5(2) . . ?
C6 C5 H5 127.2 . . ?
C4 C5 H5 127.2 . . ?
N3 C6 C5 114.2(3) . . ?
N3 C6 H6 122.9 . . ?
C5 C6 H6 122.9 . . ?
C1 N1 C4 114.5(2) . . ?
N3 N2 C3 124.2(2) . . ?
N3 N2 C4 112.8(2) . . ?
C3 N2 C4 123.0(2) . . ?
C6 N3 N2 102.5(2) . . ?
C3 N4 H4A 120.0 . . ?
C3 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?

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 C3 1.2(4) . . . . ?
Cl1 C1 C2 C3 -177.6(2) . . . . ?
C1 C2 C3 N4 177.6(3) . . . . ?
C1 C2 C3 N2 -1.3(4) . . . . ?
N1 C4 C5 C6 178.3(3) . . . . ?
N2 C4 C5 C6 -1.0(3) . . . . ?
C4 C5 C6 N3 0.8(3) . . . . ?
C2 C1 N1 C4 -0.2(4) . . . . ?
Cl1 C1 N1 C4 178.66(19) . . . . ?
C5 C4 N1 C1 -179.8(3) . . . . ?
N2 C4 N1 C1 -0.6(4) . . . . ?
N4 C3 N2 N3 0.3(4) . . . . ?
C2 C3 N2 N3 179.3(2) . . . . ?
N4 C3 N2 C4 -178.4(2) . . . . ?
C2 C3 N2 C4 0.6(4) . . . . ?
N1 C4 N2 N3 -178.4(2) . . . . ?
C5 C4 N2 N3 1.0(3) . . . . ?
N1 C4 N2 C3 0.4(4) . . . . ?
C5 C4 N2 C3 179.8(2) . . . . ?
C5 C6 N3 N2 -0.2(3) . . . . ?
C3 N2 N3 C6 -179.3(2) . . . . ?
C4 N2 N3 C6 -0.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4B N1 0.86 2.31 3.101(3) 152.5 4_566 yes
N4 H4A N3 0.86 2.22 3.008(3) 152.9 3_566 yes

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.261
_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_YF027_a
_database_code_depnum_ccdc_archive 'CCDC 2016542'
loop_
_audit_author_name
_audit_author_address
'Feng Yang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-07-15 deposited with the CCDC.	2021-03-11 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         'C6 H3 Cl N6 O4, C2 H3 N'
_chemical_formula_sum            'C8 H6 Cl N7 O4'
_chemical_formula_weight         299.65

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'
Cl Cl 0.1484 0.1585 '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                   11.0127(13)
_cell_length_b                   4.6953(7)
_cell_length_c                   23.988(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.872(4)
_cell_angle_gamma                90
_cell_volume                     1237.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2713
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      23.32

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.336
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6327
_exptl_absorpt_correction_T_max  0.7455
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11982
_diffrn_reflns_av_unetI/netI     0.0809
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.430
_diffrn_reflns_theta_max         27.566
_diffrn_reflns_theta_full        25.242
_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 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2846
_reflns_number_gt                1441
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0762P)²+0.6350P] 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         2846
_refine_ls_number_parameters     192
_refine_ls_number_restraints     35
_refine_ls_R_factor_all          0.1559
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.1769
_refine_ls_wR_factor_gt          0.1433
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1323(3) 0.3394(7) 0.44346(14) 0.0462(9) Uani 1 1 d . . . . .
H1 H 0.062671 0.432223 0.453741 0.055 Uiso 1 1 calc R U . . .
C2 C 0.1922(3) 0.1331(7) 0.47597(13) 0.0407(8) Uani 1 1 d . . . . .
C3 C 0.2913(3) 0.0428(7) 0.44627(13) 0.0391(8) Uani 1 1 d . . . . .
C4 C 0.4621(3) -0.1632(7) 0.41864(15) 0.0496(9) Uani 1 1 d . . . . .
C5 C 0.4563(3) -0.0032(8) 0.36885(14) 0.0500(9) Uani 1 1 d . . . . .
C6 C 0.3619(3) 0.1939(8) 0.35764(14) 0.0460(9) Uani 1 1 d . . . . .
Cl1 Cl 0.57442(8) -0.3996(2) 0.43441(4) 0.0660(4) Uani 1 1 d . . . . .
N1 N 0.2815(2) 0.2068(6) 0.39927(10) 0.0408(7) Uani 1 1 d . . . . .
N2 N 0.1836(2) 0.3914(6) 0.39657(11) 0.0498(7) Uani 1 1 d . . . . .
N3 N 0.3819(2) -0.1431(5) 0.45709(11) 0.0449(7) Uani 1 1 d . . . . .
N4 N 0.1598(3) 0.0281(7) 0.52824(12) 0.0506(7) Uani 1 1 d . . . . .
O1 O 0.0771(2) 0.1497(6) 0.55046(10) 0.0622(7) Uani 1 1 d . . . . .
O2 O 0.2142(3) -0.1771(6) 0.54898(12) 0.0835(10) Uani 1 1 d . . . . .
N5 N 0.5459(3) -0.0321(11) 0.32737(16) 0.0791(11) Uani 1 1 d . U . . .
O3A O 0.6509(8) -0.067(3) 0.3436(5) 0.106(4) Uani 0.406(12) 1 d . U P A 1
O3B O 0.5994(7) -0.279(2) 0.3253(3) 0.104(3) Uani 0.594(12) 1 d . U P A 2
O4 O 0.5404(4) 0.1067(10) 0.28778(17) 0.1344(16) Uani 1 1 d . U . . .
N6 N 0.3404(3) 0.3645(7) 0.31539(12) 0.0616(9) Uani 1 1 d . . . . .
H6A H 0.278681 0.477108 0.314505 0.074 Uiso 1 1 calc R U . . .
H6B H 0.387807 0.364668 0.288340 0.074 Uiso 1 1 calc R U . . .
N7 N 0.1643(4) 0.7992(12) 0.2702(2) 0.1230(18) Uani 1 1 d . . . . .
C7 C 0.1395(4) 0.8866(11) 0.2276(2) 0.0793(13) Uani 1 1 d . . . . .
C8 C 0.1084(4) 1.0015(15) 0.1730(2) 0.1128(19) Uani 1 1 d . . . . .
H6 H 0.126510 1.201552 0.172920 0.169 Uiso 1 1 calc R U . . .
H5 H 0.023207 0.973441 0.163519 0.169 Uiso 1 1 calc R U . . .
H4 H 0.154882 0.906472 0.146121 0.169 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 N2 1.315(4) . ?
C1 C2 1.383(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.408(4) . ?
C2 N4 1.415(4) . ?
C3 N3 1.337(4) . ?
C3 N1 1.363(4) . ?
C4 N3 1.323(4) . ?
C4 C5 1.409(5) . ?
C4 Cl1 1.686(4) . ?
C5 C6 1.404(5) . ?
C5 N5 1.455(5) . ?
C6 N6 1.301(4) . ?
C6 N1 1.380(4) . ?
N1 N2 1.382(3) . ?
N4 O2 1.222(4) . ?
N4 O1 1.227(3) . ?
N5 O4 1.150(5) . ?
N5 O3A 1.207(10) . ?
N5 O3B 1.302(8) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N7 C7 1.117(5) . ?
C7 C8 1.436(7) . ?
C8 H6 0.9600 . ?
C8 H5 0.9600 . ?
C8 H4 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
N2 C1 C2 113.3(3) . . ?
N2 C1 H1 123.3 . . ?
C2 C1 H1 123.3 . . ?
C1 C2 C3 106.4(3) . . ?
C1 C2 N4 127.2(3) . . ?
C3 C2 N4 126.4(3) . . ?
N3 C3 N1 123.0(3) . . ?
N3 C3 C2 133.8(3) . . ?
N1 C3 C2 103.2(3) . . ?
N3 C4 C5 124.0(3) . . ?
N3 C4 Cl1 113.9(3) . . ?
C5 C4 Cl1 122.1(3) . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 N5 117.3(4) . . ?
C4 C5 N5 122.4(4) . . ?
N6 C6 N1 116.4(3) . . ?
N6 C6 C5 130.5(3) . . ?
N1 C6 C5 113.2(3) . . ?
C3 N1 C6 123.7(3) . . ?
C3 N1 N2 114.3(2) . . ?
C6 N1 N2 122.0(3) . . ?
C1 N2 N1 102.8(2) . . ?
C4 N3 C3 115.8(3) . . ?
O2 N4 O1 123.2(3) . . ?
O2 N4 C2 119.3(3) . . ?
O1 N4 C2 117.5(3) . . ?
O4 N5 O3A 109.9(6) . . ?
O4 N5 O3B 118.1(4) . . ?
O4 N5 C5 120.8(4) . . ?
O3A N5 C5 118.1(6) . . ?
O3B N5 C5 116.0(5) . . ?
C6 N6 H6A 120.0 . . ?
C6 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
N7 C7 C8 179.4(6) . . ?
C7 C8 H6 109.5 . . ?
C7 C8 H5 109.5 . . ?
H6 C8 H5 109.5 . . ?
C7 C8 H4 109.5 . . ?
H6 C8 H4 109.5 . . ?
H5 C8 H4 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
N2 C1 C2 C3 -0.6(4) . . . . ?
N2 C1 C2 N4 -179.5(3) . . . . ?
C1 C2 C3 N3 177.9(3) . . . . ?
N4 C2 C3 N3 -3.2(6) . . . . ?
C1 C2 C3 N1 0.7(3) . . . . ?
N4 C2 C3 N1 179.6(3) . . . . ?
N3 C4 C5 C6 0.5(5) . . . . ?
Cl1 C4 C5 C6 -179.3(3) . . . . ?
N3 C4 C5 N5 -179.7(3) . . . . ?
Cl1 C4 C5 N5 0.6(5) . . . . ?
C4 C5 C6 N6 178.8(3) . . . . ?
N5 C5 C6 N6 -1.0(6) . . . . ?
C4 C5 C6 N1 -0.1(5) . . . . ?
N5 C5 C6 N1 -179.9(3) . . . . ?
N3 C3 N1 C6 1.5(5) . . . . ?
C2 C3 N1 C6 179.0(3) . . . . ?
N3 C3 N1 N2 -178.2(3) . . . . ?
C2 C3 N1 N2 -0.6(3) . . . . ?
N6 C6 N1 C3 -179.9(3) . . . . ?
C5 C6 N1 C3 -0.8(4) . . . . ?
N6 C6 N1 N2 -0.3(4) . . . . ?
C5 C6 N1 N2 178.8(3) . . . . ?
C2 C1 N2 N1 0.2(4) . . . . ?
C3 N1 N2 C1 0.3(3) . . . . ?
C6 N1 N2 C1 -179.4(3) . . . . ?
C5 C4 N3 C3 0.1(5) . . . . ?
Cl1 C4 N3 C3 179.8(2) . . . . ?
N1 C3 N3 C4 -1.0(4) . . . . ?
C2 C3 N3 C4 -177.7(3) . . . . ?
C1 C2 N4 O2 171.9(3) . . . . ?
C3 C2 N4 O2 -6.8(5) . . . . ?
C1 C2 N4 O1 -7.8(5) . . . . ?
C3 C2 N4 O1 173.5(3) . . . . ?
C6 C5 N5 O4 1.8(7) . . . . ?
C4 C5 N5 O4 -178.1(4) . . . . ?
C6 C5 N5 O3A 142.0(10) . . . . ?
C4 C5 N5 O3A -37.9(11) . . . . ?
C6 C5 N5 O3B -152.6(5) . . . . ?
C4 C5 N5 O3B 27.6(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C8 H6 O3A^a 0.96 2.73 3.379(11) 125.2 2_665 yes
N6 H6B O4 0.86 2.33 3.095(4) 147.8 2_655 yes
N6 H6B O4 0.86 2.07 2.637(5) 122.6 . yes
N6 H6A N7 0.86 2.20 2.969(6) 149.5 . yes
C1 H1 O1 0.93 2.49 3.338(4) 151.2 3_566 yes

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_YF_047_a
_database_code_depnum_ccdc_archive 'CCDC 2053258'
loop_
_audit_author_name
_audit_author_address
'Feng Yang'
;Nanjing University Of Science And Technology
China
;
_audit_update_record             
;
2021-02-24 deposited with the CCDC.	2021-03-11 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         ' C6 H4 N6 O5, C2 H4 O2, 0.125(H2 O)'
_chemical_formula_sum            'C8 H8.25 N6 O7.12'
_chemical_formula_weight         302.46

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                   4.5803(3)
_cell_length_b                   27.1194(17)
_cell_length_c                   10.7559(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.380(2)
_cell_angle_gamma                90
_cell_volume                     1318.18(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4534
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.31

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_F_000             621
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.135
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            11523
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.437
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_full        24.991
_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             2297
_reflns_number_gt                1739
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0880P)²+0.8839P] 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         2297
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1700
_refine_ls_wR_factor_gt          0.1552
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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 0.1752(5) 0.77058(9) 0.4740(2) 0.0286(6) Uani 1 1 d . . . . .
C2 C 0.2890(5) 0.73107(9) 0.4101(2) 0.0304(6) Uani 1 1 d . . . . .
C3 C 0.4753(5) 0.73815(9) 0.3159(2) 0.0298(6) Uani 1 1 d . . . . .
C4 C 0.4195(5) 0.82665(9) 0.3552(2) 0.0300(6) Uani 1 1 d . . . . .
C5 C 0.5240(6) 0.86892(9) 0.3059(3) 0.0366(7) Uani 1 1 d . . . . .
C6 C 0.6875(6) 0.85323(10) 0.2147(3) 0.0386(7) Uani 1 1 d . . . . .
H6 H 0.782323 0.874405 0.166150 0.046 Uiso 1 1 calc R U . . .
C7 C 0.9467(9) 0.54614(12) 0.1501(4) 0.0710(11) Uani 1 1 d . . . . .
H7A H 1.014133 0.541601 0.070943 0.107 Uiso 1 1 d R U . . .
H7B H 0.784081 0.524282 0.154947 0.107 Uiso 1 1 d R U . . .
H7C H 1.105355 0.539029 0.217746 0.107 Uiso 1 1 d R U . . .
C8 C 0.8490(7) 0.59778(11) 0.1606(3) 0.0450(7) Uani 1 1 d . . . . .
N1 N 0.2519(5) 0.81756(8) 0.4452(2) 0.0326(5) Uani 1 1 d . . . . .
H1 H 0.191853 0.841942 0.485431 0.039 Uiso 1 1 calc R U . . .
N2 N 0.5229(5) 0.78872(8) 0.29380(19) 0.0309(5) Uani 1 1 d . . . . .
N3 N 0.6916(5) 0.80479(9) 0.2056(2) 0.0382(6) Uani 1 1 d . . . . .
N4 N -0.0016(5) 0.76767(8) 0.5582(2) 0.0347(6) Uani 1 1 d . . . . .
H4A H -0.060233 0.794114 0.590724 0.042 Uiso 1 1 calc R U . . .
H4B H -0.058812 0.739332 0.580798 0.042 Uiso 1 1 calc R U . . .
N5 N 0.2193(5) 0.68168(8) 0.4399(2) 0.0379(6) Uani 1 1 d . . . . .
N7 N 0.4754(6) 0.91745(9) 0.3458(3) 0.0496(7) Uani 1 1 d . . . . .
O1 O 0.0603(5) 0.67435(7) 0.5194(2) 0.0588(7) Uani 1 1 d . . . . .
O2 O 0.3205(7) 0.64750(8) 0.3892(3) 0.0854(10) Uani 1 1 d . . . . .
O3 O 0.5987(7) 0.95145(9) 0.3014(3) 0.0811(9) Uani 1 1 d . . . . .
O4 O 0.3127(6) 0.92251(8) 0.4251(3) 0.0654(7) Uani 1 1 d . . . . .
O5 O 0.6776(5) 0.60383(8) 0.2458(2) 0.0610(7) Uani 1 1 d . . . . .
H5 H 0.629657 0.632908 0.247955 0.091 Uiso 1 1 calc R U . . .
O6 O 0.9165(5) 0.63160(7) 0.0979(2) 0.0547(6) Uani 1 1 d . . . . .
O7 O 0.5923(4) 0.70807(7) 0.25575(18) 0.0408(5) Uani 1 1 d . . . . .
O8 O 0.089(5) 0.5587(8) 0.607(2) 0.080(6) Uani 0.125 1 d . . P . .


_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 1.312(3) . ?
C1 N1 1.371(3) . ?
C1 C2 1.417(4) . ?
C2 N5 1.425(3) . ?
C2 C3 1.440(4) . ?
C3 O7 1.218(3) . ?
C3 N2 1.415(3) . ?
C4 N2 1.349(3) . ?
C4 N1 1.352(3) . ?
C4 C5 1.381(4) . ?
C5 C6 1.394(4) . ?
C5 N7 1.413(4) . ?
C6 N3 1.318(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.480(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 O6 1.208(3) . ?
C8 O5 1.311(4) . ?
N1 H1 0.8600 . ?
N2 N3 1.388(3) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 O2 1.206(3) . ?
N5 O1 1.227(3) . ?
N7 O3 1.219(3) . ?
N7 O4 1.228(3) . ?
O5 H5 0.8200 . ?

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 115.0(2) . . ?
N4 C1 C2 127.3(2) . . ?
N1 C1 C2 117.7(2) . . ?
C1 C2 N5 119.2(2) . . ?
C1 C2 C3 123.2(2) . . ?
N5 C2 C3 117.6(2) . . ?
O7 C3 N2 117.8(2) . . ?
O7 C3 C2 130.3(2) . . ?
N2 C3 C2 111.9(2) . . ?
N2 C4 N1 119.8(2) . . ?
N2 C4 C5 105.9(2) . . ?
N1 C4 C5 134.3(2) . . ?
C4 C5 C6 106.0(2) . . ?
C4 C5 N7 125.1(2) . . ?
C6 C5 N7 128.9(2) . . ?
N3 C6 C5 111.9(2) . . ?
N3 C6 H6 124.1 . . ?
C5 C6 H6 124.1 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O6 C8 O5 122.2(3) . . ?
O6 C8 C7 124.6(3) . . ?
O5 C8 C7 113.2(3) . . ?
C4 N1 C1 121.9(2) . . ?
C4 N1 H1 119.1 . . ?
C1 N1 H1 119.1 . . ?
C4 N2 N3 112.0(2) . . ?
C4 N2 C3 125.5(2) . . ?
N3 N2 C3 122.5(2) . . ?
C6 N3 N2 104.2(2) . . ?
C1 N4 H4A 120.0 . . ?
C1 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
O2 N5 O1 120.4(2) . . ?
O2 N5 C2 120.3(2) . . ?
O1 N5 C2 119.3(2) . . ?
O3 N7 O4 124.1(3) . . ?
O3 N7 C5 118.6(3) . . ?
O4 N7 C5 117.3(2) . . ?
C8 O5 H5 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 -2.4(4) . . . . ?
N1 C1 C2 N5 178.5(2) . . . . ?
N4 C1 C2 C3 178.0(2) . . . . ?
N1 C1 C2 C3 -1.1(4) . . . . ?
C1 C2 C3 O7 178.5(3) . . . . ?
N5 C2 C3 O7 -1.2(4) . . . . ?
C1 C2 C3 N2 -1.4(3) . . . . ?
N5 C2 C3 N2 179.0(2) . . . . ?
N2 C4 C5 C6 0.3(3) . . . . ?
N1 C4 C5 C6 179.7(3) . . . . ?
N2 C4 C5 N7 -178.1(3) . . . . ?
N1 C4 C5 N7 1.3(5) . . . . ?
C4 C5 C6 N3 -0.4(3) . . . . ?
N7 C5 C6 N3 177.9(3) . . . . ?
N2 C4 N1 C1 -2.0(4) . . . . ?
C5 C4 N1 C1 178.7(3) . . . . ?
N4 C1 N1 C4 -176.3(2) . . . . ?
C2 C1 N1 C4 2.9(3) . . . . ?
N1 C4 N2 N3 -179.6(2) . . . . ?
C5 C4 N2 N3 -0.1(3) . . . . ?
N1 C4 N2 C3 -0.9(4) . . . . ?
C5 C4 N2 C3 178.6(2) . . . . ?
O7 C3 N2 C4 -177.4(2) . . . . ?
C2 C3 N2 C4 2.5(3) . . . . ?
O7 C3 N2 N3 1.1(4) . . . . ?
C2 C3 N2 N3 -179.0(2) . . . . ?
C5 C6 N3 N2 0.3(3) . . . . ?
C4 N2 N3 C6 -0.1(3) . . . . ?
C3 N2 N3 C6 -178.9(2) . . . . ?
C1 C2 N5 O2 -178.0(3) . . . . ?
C3 C2 N5 O2 1.7(4) . . . . ?
C1 C2 N5 O1 0.6(4) . . . . ?
C3 C2 N5 O1 -179.7(2) . . . . ?
C4 C5 N7 O3 174.4(3) . . . . ?
C6 C5 N7 O3 -3.6(5) . . . . ?
C4 C5 N7 O4 -4.7(5) . . . . ?
C6 C5 N7 O4 177.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H5 O7 0.82 2.05 2.858(3) 169.3 . yes
O5 H5 O2 0.82 2.27 2.698(3) 112.6 . yes
N4 H4B O1 0.86 1.99 2.588(3) 125.8 . yes
N4 H4B N3 0.86 2.24 3.013(3) 148.7 4_476 yes
N4 H4A O7 0.86 2.57 3.114(3) 122.1 4_476 yes
N4 H4A O6 0.86 2.02 2.800(3) 150.4 4_476 yes
N1 H1 O6 0.86 2.02 2.790(3) 149.2 4_476 yes
N1 H1 O4 0.86 2.37 2.871(3) 117.6 . yes
C7 H7A O4 0.96 2.44 3.273(4) 144.4 4_675 yes
C6 H6 O1 0.93 2.55 3.009(4) 110.7 4_675 yes

_refine_diff_density_max         0.567
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.074


# start Validation Reply Form
_vrf_PLAT041_YF_047_a            
;
PROBLEM: Calc. and Reported SumFormula Strings Differ Please Check
RESPONSE: As it was not possible to see clear electron-density peaks 
in difference maps which would correspond with acceptable locations 
for the O8 water H atoms??the refinement was completed
 with no allowance for these H atoms in the model.
;

# end Validation Reply Form

####################################################################### 
# 
# 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_YF023_a
_database_code_depnum_ccdc_archive 'CCDC 2007915'
loop_
_audit_author_name
_audit_author_address
'Feng Yang'
;Nanjing University Of Science And Technology
China
;
_audit_update_record             
;
2021-02-24 deposited with the CCDC.	2021-03-11 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         '2(C6 H5 N7 O4), 5(H2 O)'
_chemical_formula_sum            'C12 H20 N14 O13'
_chemical_formula_weight         568.42

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   3.538(2)
_cell_length_b                   12.804(6)
_cell_length_c                   13.613(7)
_cell_angle_alpha                64.235(12)
_cell_angle_beta                 83.900(16)
_cell_angle_gamma                82.879(16)
_cell_volume                     550.2(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2279
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      24.39

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_F_000             294
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.154
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5750
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5639
_diffrn_reflns_av_unetI/netI     0.0876
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.773
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             1858
_reflns_number_gt                1199
_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)+(0.0060P)²+6.5000P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.062(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1858
_refine_ls_number_parameters     182
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1986
_refine_ls_R_factor_gt           0.1553
_refine_ls_wR_factor_ref         0.3309
_refine_ls_wR_factor_gt          0.3126
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.154
_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 0.495(3) 0.2001(8) 0.2981(7) 0.043(2) Uani 1 1 d . . . . .
C2 C 0.576(3) 0.3170(8) 0.2678(8) 0.046(3) Uani 1 1 d . . . . .
C3 C 0.724(3) 0.3880(8) 0.1604(8) 0.043(2) Uani 1 1 d . . . . .
C4 C 0.700(3) 0.2449(7) 0.1093(7) 0.037(2) Uani 1 1 d . . . . .
C5 C 0.714(3) 0.1740(8) 0.0509(7) 0.047(3) Uani 1 1 d . . . . .
C6 C 0.591(3) 0.0683(8) 0.1236(8) 0.051(3) Uani 1 1 d . . . . .
H6 H 0.571103 0.007380 0.105014 0.061 Uiso 1 1 calc R U . . .
N1 N 0.793(2) 0.3494(6) 0.0837(6) 0.041(2) Uani 1 1 d . . . . .
N2 N 0.569(3) 0.1713(6) 0.2110(6) 0.044(2) Uani 1 1 d . . . . .
N3 N 0.506(3) 0.0627(7) 0.2187(7) 0.054(2) Uani 1 1 d . . . . .
N4 N 0.372(3) 0.1271(6) 0.3835(5) 0.041(2) Uani 1 1 d . . . . .
N5 N 0.485(3) 0.3606(7) 0.3473(7) 0.057(3) Uani 1 1 d . . . . .
N6 N 0.818(3) 0.4936(6) 0.1328(6) 0.053(3) Uani 1 1 d . . . . .
H6A H 0.917851 0.532861 0.068443 0.064 Uiso 1 1 calc R U . . .
H6B H 0.780396 0.523426 0.179045 0.064 Uiso 1 1 calc R U . . .
N7 N 0.823(3) 0.2077(7) -0.0594(7) 0.051(2) Uani 1 1 d . . . . .
O1 O 0.328(3) 0.3021(6) 0.4350(6) 0.082(3) Uani 1 1 d . . . . .
O2 O 0.564(3) 0.4591(6) 0.3281(6) 0.085(3) Uani 1 1 d . . . . .
O3 O 0.954(3) 0.3002(6) -0.1146(6) 0.067(2) Uani 1 1 d . . . . .
O4 O 0.792(3) 0.1391(6) -0.0983(6) 0.073(3) Uani 1 1 d . . . . .
O5 O 0.921(4) 0.1025(9) 0.5838(8) 0.118(4) Uani 1 1 d . . . . .
O6 O 0.883(9) 0.503(4) 0.493(4) 0.132(11) Uani 0.5 1 d . U P A -1
O7 O 0.076(7) 0.7312(15) 0.3347(11) 0.197(7) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N4 1.209(11) . ?
C1 N2 1.379(11) . ?
C1 C2 1.427(12) . ?
C2 N5 1.411(12) . ?
C2 C3 1.429(12) . ?
C3 N6 1.312(11) . ?
C3 N1 1.326(11) . ?
C4 N1 1.304(11) . ?
C4 N2 1.363(11) . ?
C4 C5 1.437(13) . ?
C5 C6 1.376(13) . ?
C5 N7 1.394(11) . ?
C6 N3 1.270(12) . ?
C6 H6 0.9300 . ?
N2 N3 1.392(10) . ?
N5 O1 1.217(10) . ?
N5 O2 1.234(10) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N7 O3 1.213(10) . ?
N7 O4 1.227(9) . ?

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 N2 117.7(8) . . ?
N4 C1 C2 131.3(9) . . ?
N2 C1 C2 111.0(8) . . ?
N5 C2 C1 116.8(8) . . ?
N5 C2 C3 121.7(8) . . ?
C1 C2 C3 121.4(9) . . ?
N6 C3 N1 115.7(8) . . ?
N6 C3 C2 122.2(8) . . ?
N1 C3 C2 122.1(8) . . ?
N1 C4 N2 124.2(8) . . ?
N1 C4 C5 134.1(8) . . ?
N2 C4 C5 101.6(7) . . ?
C6 C5 N7 126.6(9) . . ?
C6 C5 C4 107.1(8) . . ?
N7 C5 C4 126.2(8) . . ?
N3 C6 C5 112.8(9) . . ?
N3 C6 H6 123.6 . . ?
C5 C6 H6 123.6 . . ?
C4 N1 C3 116.6(7) . . ?
C4 N2 C1 124.4(7) . . ?
C4 N2 N3 113.2(7) . . ?
C1 N2 N3 122.3(7) . . ?
C6 N3 N2 105.2(7) . . ?
O1 N5 O2 119.2(8) . . ?
O1 N5 C2 120.7(8) . . ?
O2 N5 C2 120.1(8) . . ?
C3 N6 H6A 120.0 . . ?
C3 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
O3 N7 O4 120.8(8) . . ?
O3 N7 C5 121.3(8) . . ?
O4 N7 C5 117.8(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 C1 C2 N5 -3.3(18) . . . . ?
N2 C1 C2 N5 175.3(10) . . . . ?
N4 C1 C2 C3 179.7(12) . . . . ?
N2 C1 C2 C3 -1.7(14) . . . . ?
N5 C2 C3 N6 6.6(16) . . . . ?
C1 C2 C3 N6 -176.5(11) . . . . ?
N5 C2 C3 N1 -176.8(10) . . . . ?
C1 C2 C3 N1 0.1(16) . . . . ?
N1 C4 C5 C6 177.4(11) . . . . ?
N2 C4 C5 C6 0.1(12) . . . . ?
N1 C4 C5 N7 -4(2) . . . . ?
N2 C4 C5 N7 178.4(11) . . . . ?
N7 C5 C6 N3 -179.1(11) . . . . ?
C4 C5 C6 N3 -0.8(14) . . . . ?
N2 C4 N1 C3 -5.6(14) . . . . ?
C5 C4 N1 C3 177.5(11) . . . . ?
N6 C3 N1 C4 -179.7(9) . . . . ?
C2 C3 N1 C4 3.5(15) . . . . ?
N1 C4 N2 C1 4.1(16) . . . . ?
C5 C4 N2 C1 -178.2(10) . . . . ?
N1 C4 N2 N3 -177.2(9) . . . . ?
C5 C4 N2 N3 0.5(11) . . . . ?
N4 C1 N2 C4 178.6(10) . . . . ?
C2 C1 N2 C4 -0.2(14) . . . . ?
N4 C1 N2 N3 0.0(15) . . . . ?
C2 C1 N2 N3 -178.8(9) . . . . ?
C5 C6 N3 N2 1.0(13) . . . . ?
C4 N2 N3 C6 -1.0(12) . . . . ?
C1 N2 N3 C6 177.8(10) . . . . ?
C1 C2 N5 O1 -3.6(16) . . . . ?
C3 C2 N5 O1 173.5(11) . . . . ?
C1 C2 N5 O2 176.7(11) . . . . ?
C3 C2 N5 O2 -6.2(17) . . . . ?
C6 C5 N7 O3 -174.6(12) . . . . ?
C4 C5 N7 O3 7.4(17) . . . . ?
C6 C5 N7 O4 3.2(17) . . . . ?
C4 C5 N7 O4 -174.8(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C6 H6 O4 0.93 2.44 3.284(12) 151.1 2_655 yes
N6 H6A N1 0.86 2.20 3.048(10) 170.4 2_765 yes
N6 H6B O2 0.86 1.94 2.578(11) 130.2 . yes
N6 H6B O3 0.86 2.32 2.757(10) 111.8 2_765 yes

_refine_diff_density_max         0.563
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.121

# start Validation Reply Form
_vrf_PLAT043_YF023_a             
;
PROBLEM: Calculated and Reported Mol. Weight Differ by .. 14.11 Check
RESPONSE: As it was not possible to see clear electron-density peaks
 in difference maps which would correspond with acceptable locations 
for the various water H atoms and those at N4,  
the refinement was completed with no allowance for these H atoms in the model.
;
_vrf_PLAT306_YF023_a             
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) ....... O5 Check
RESPONSE: As it was not possible to see clear electron-density peaks
 in difference maps which would correspond with acceptable locations 
for the various water H atoms and those at N4,  
the refinement was completed with no allowance for these H atoms in the model.
;

_vrf_PLAT430_YF023_a             
;
PROBLEM: Short Inter D...A Contact O5 ..O7 . 2.80 Ang.
RESPONSE: As it was not possible to see clear electron-density peaks
 in difference maps which would correspond with acceptable locations 
for the various water H atoms and those at N4,  
the refinement was completed with no allowance for these H atoms in the model.
;
# end Validation Reply Form


