# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_SQSAN10_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2281788'
loop_
_audit_author_name
_audit_author_address
'Qi Sun'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-07-16 deposited with the CCDC.	2023-10-17 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            'C6 H N9 O7'
_chemical_formula_weight         311.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   6.404(2)
_cell_length_b                   21.152(7)
_cell_length_c                   8.235(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1115.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3729
_cell_measurement_theta_min      3.636
_cell_measurement_theta_max      53.583

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.853
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.963
_shelx_estimated_absorpt_T_min   0.816
_shelx_estimated_absorpt_T_max   0.846
_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      150(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4693
_diffrn_reflns_av_unetI/netI     0.0919
_diffrn_reflns_av_R_equivalents  0.0862
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.636
_diffrn_reflns_theta_max         52.995
_diffrn_reflns_theta_full        52.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.920
_reflns_number_total             1811
_reflns_number_gt                1509
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_max     0.836
_reflns_Friedel_fraction_full    0.837

_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)+(0.1239P)²+6.7132P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.043(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 453 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1811
_refine_ls_number_parameters     218
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.1225
_refine_ls_R_factor_gt           0.1040
_refine_ls_wR_factor_ref         0.2906
_refine_ls_wR_factor_gt          0.2773
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.095
_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
O16A O 0.181(4) 0.4352(10) 0.619(2) 0.090(7) Uani 0.7 1 d D U P A 1
N1 N -0.0697(18) 0.0607(6) -0.4717(15) 0.043(3) Uani 1 1 d . . . A 1
N2 N -0.1128(16) 0.1156(5) -0.3978(15) 0.035(3) Uani 1 1 d . . . A 1
N3 N 0.0865(16) 0.0848(5) -0.1538(14) 0.035(3) Uani 1 1 d . . . A 1
H3 H 0.1392 0.0479 -0.1815 0.042 Uiso 1 1 calc R U . A 1
N4 N 0.1183(16) 0.1138(5) -0.0015(14) 0.039(3) Uani 1 1 d . . . A 1
N5 N -0.0851(16) 0.2681(5) 0.0990(15) 0.036(2) Uani 1 1 d . . . A 1
N6 N 0.094(2) 0.2585(5) 0.3392(17) 0.051(3) Uani 1 1 d . . . A 1
N8 N -0.126(3) 0.4532(6) 0.4065(18) 0.072(5) Uani 1 1 d . . . A 1
N9 N -0.275(2) 0.3794(5) 0.2370(18) 0.054(3) Uani 1 1 d . . . A 1
O10 O -0.1361(14) 0.0552(5) -0.6146(11) 0.045(3) Uani 1 1 d . . . A 1
O11 O 0.0250(15) 0.0166(4) -0.4033(14) 0.044(2) Uani 1 1 d . . . A 1
O12 O -0.0740(13) 0.1741(4) -0.1649(12) 0.035(2) Uani 1 1 d . . . A 1
O13 O 0.1201(13) 0.2038(5) 0.2449(13) 0.045(3) Uani 1 1 d . . . A 1
O14 O -0.295(3) 0.4376(6) 0.3009(17) 0.082(5) Uani 1 1 d . . . A 1
N7 N 0.183(3) 0.4020(6) 0.5022(17) 0.074(4) Uani 1 1 d D U . A 1
O15A O 0.319(3) 0.3677(7) 0.445(3) 0.083(6) Uani 0.7 1 d D U P A 1
O15B O 0.262(6) 0.3511(15) 0.518(6) 0.094(10) Uani 0.3 1 d D U P A 1
O16B O 0.196(8) 0.450(2) 0.590(7) 0.086(10) Uani 0.3 1 d D U P A 1
C17 C -0.0308(18) 0.1194(5) -0.2487(16) 0.032(3) Uani 1 1 d . . . A 1
C18 C 0.022(2) 0.1656(6) -0.0179(18) 0.038(3) Uani 1 1 d . . . A 1
C19 C 0.011(2) 0.2149(6) 0.101(2) 0.043(3) Uani 1 1 d . . . A 1
C20 C -0.032(2) 0.2939(7) 0.2505(17) 0.046(4) Uani 1 1 d . . . A 1
C21 C -0.102(2) 0.3553(7) 0.2978(17) 0.045(3) Uani 1 1 d . . . A 1
C22 C -0.014(3) 0.4021(6) 0.4039(18) 0.052(4) Uani 1 1 d D . . A 1


_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
O16A N7 1.193(18) . ?
N1 O11 1.247(14) . ?
N1 O10 1.256(14) . ?
N1 N2 1.340(15) . ?
N2 C17 1.338(18) . ?
N3 C17 1.308(16) . ?
N3 N4 1.411(16) . ?
N3 H3 0.8800 . ?
N4 C18 1.264(16) . ?
N5 C19 1.282(16) . ?
N5 C20 1.404(19) . ?
N6 C20 1.32(2) . ?
N6 O13 1.403(15) . ?
N8 C22 1.30(2) . ?
N8 O14 1.43(2) . ?
N9 C21 1.32(2) . ?
N9 O14 1.344(17) . ?
O12 C18 1.369(17) . ?
O12 C17 1.376(14) . ?
O13 C19 1.398(19) . ?
N7 O15B 1.20(2) . ?
N7 O15A 1.224(18) . ?
N7 O16B 1.24(2) . ?
N7 C22 1.50(2) . ?
C18 C19 1.431(18) . ?
C20 C21 1.43(2) . ?
C21 C22 1.43(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
O11 N1 O10 121.3(12) . . ?
O11 N1 N2 122.9(12) . . ?
O10 N1 N2 115.8(11) . . ?
C17 N2 N1 112.8(10) . . ?
C17 N3 N4 111.8(10) . . ?
C17 N3 H3 124.1 . . ?
N4 N3 H3 124.1 . . ?
C18 N4 N3 102.2(11) . . ?
C19 N5 C20 102.4(13) . . ?
C20 N6 O13 103.5(11) . . ?
C22 N8 O14 102.4(13) . . ?
C21 N9 O14 106.6(15) . . ?
C18 O12 C17 104.0(10) . . ?
C19 O13 N6 105.8(10) . . ?
N9 O14 N8 112.2(13) . . ?
O15B N7 O16A 117(3) . . ?
O15B N7 O15A 38(3) . . ?
O16A N7 O15A 132(2) . . ?
O15B N7 O16B 130(3) . . ?
O16A N7 O16B 19(4) . . ?
O15A N7 O16B 131(3) . . ?
O15B N7 C22 114.7(17) . . ?
O16A N7 C22 115.0(16) . . ?
O15A N7 C22 113.1(12) . . ?
O16B N7 C22 111.5(16) . . ?
N3 C17 N2 137.8(11) . . ?
N3 C17 O12 106.7(11) . . ?
N2 C17 O12 115.6(10) . . ?
N4 C18 O12 115.3(12) . . ?
N4 C18 C19 125.7(13) . . ?
O12 C18 C19 119.0(11) . . ?
N5 C19 O13 113.3(14) . . ?
N5 C19 C18 131.0(15) . . ?
O13 C19 C18 115.6(11) . . ?
N6 C20 N5 114.8(13) . . ?
N6 C20 C21 123.8(14) . . ?
N5 C20 C21 121.3(13) . . ?
N9 C21 C20 120.7(14) . . ?
N9 C21 C22 107.0(12) . . ?
C20 C21 C22 132.2(14) . . ?
N8 C22 C21 111.7(16) . . ?
N8 C22 N7 117.3(14) . . ?
C21 C22 N7 130.9(12) . . ?

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
O11 N1 N2 C17 4.5(17) . . . . ?
O10 N1 N2 C17 -177.5(10) . . . . ?
C17 N3 N4 C18 -2.1(13) . . . . ?
C20 N6 O13 C19 3.1(15) . . . . ?
C21 N9 O14 N8 1.1(18) . . . . ?
C22 N8 O14 N9 -1.7(18) . . . . ?
N4 N3 C17 N2 -178.2(14) . . . . ?
N4 N3 C17 O12 2.5(13) . . . . ?
N1 N2 C17 N3 2(2) . . . . ?
N1 N2 C17 O12 -178.4(10) . . . . ?
C18 O12 C17 N3 -1.8(12) . . . . ?
C18 O12 C17 N2 178.7(10) . . . . ?
N3 N4 C18 O12 0.9(14) . . . . ?
N3 N4 C18 C19 -177.5(13) . . . . ?
C17 O12 C18 N4 0.5(14) . . . . ?
C17 O12 C18 C19 179.1(12) . . . . ?
C20 N5 C19 O13 1.2(15) . . . . ?
C20 N5 C19 C18 -179.7(15) . . . . ?
N6 O13 C19 N5 -2.9(16) . . . . ?
N6 O13 C19 C18 177.9(12) . . . . ?
N4 C18 C19 N5 -178.1(15) . . . . ?
O12 C18 C19 N5 4(2) . . . . ?
N4 C18 C19 O13 1(2) . . . . ?
O12 C18 C19 O13 -177.4(11) . . . . ?
O13 N6 C20 N5 -2.7(17) . . . . ?
O13 N6 C20 C21 -179.5(13) . . . . ?
C19 N5 C20 N6 1.0(17) . . . . ?
C19 N5 C20 C21 177.9(13) . . . . ?
O14 N9 C21 C20 -178.4(13) . . . . ?
O14 N9 C21 C22 0.0(17) . . . . ?
N6 C20 C21 N9 -156.9(15) . . . . ?
N5 C20 C21 N9 26(2) . . . . ?
N6 C20 C21 C22 25(3) . . . . ?
N5 C20 C21 C22 -151.4(15) . . . . ?
O14 N8 C22 C21 1.6(17) . . . . ?
O14 N8 C22 N7 179.1(12) . . . . ?
N9 C21 C22 N8 -1.1(18) . . . . ?
C20 C21 C22 N8 177.0(15) . . . . ?
N9 C21 C22 N7 -178.1(15) . . . . ?
C20 C21 C22 N7 0(3) . . . . ?
O15B N7 C22 N8 168(4) . . . . ?
O16A N7 C22 N8 29(2) . . . . ?
O15A N7 C22 N8 -150.5(17) . . . . ?
O16B N7 C22 N8 9(4) . . . . ?
O15B N7 C22 C21 -15(4) . . . . ?
O16A N7 C22 C21 -154(2) . . . . ?
O15A N7 C22 C21 26(2) . . . . ?
O16B N7 C22 C21 -174(4) . . . . ?

_refine_diff_density_max         0.586
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.151



####################################################################### 
# 
# 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_20201218fL_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2281790'
loop_
_audit_author_name
_audit_author_address
'Qi Sun'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-07-16 deposited with the CCDC.	2023-10-17 downloaded from the CCDC.
;
_audit_creation_date             2020-12-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H7 N5 O4'
_chemical_formula_sum            'C7 H7 N5 O4'
_chemical_formula_weight         225.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.9648(16)
_cell_length_b                   24.229(6)
_cell_length_c                   8.225(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.449(12)
_cell_angle_gamma                90
_cell_volume                     948.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3552
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      54.928
_cell_measurement_theta_min      3.174
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1588 before and 0.1054 after correction. The Ratio of minimum to maximum transmission is 0.5479. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0821
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7469
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.015
_diffrn_reflns_theta_min         3.174
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1311
_reflns_number_total             1788
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1788
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0686
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1348P)²+0.0442P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1884
_refine_ls_wR_factor_ref         0.2073
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 N1, C5, C3, O3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3.a Everything fixed:
 H1N(H2N)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.3736(4) 0.38620(9) 0.8951(2) 0.0588(6) Uani 1 1 d . . . . .
N1 N 0.7026(4) 0.37004(9) 0.5905(2) 0.0413(6) Uani 1 1 d . U . . .
O2 O 1.0789(4) 0.31352(8) 0.8614(2) 0.0536(6) Uani 1 1 d . . . . .
O4 O -0.0519(4) 0.38961(8) 0.1876(2) 0.0509(6) Uani 1 1 d . . . . .
N2 N 0.0064(4) 0.43948(9) 0.1161(2) 0.0451(6) Uani 1 1 d . . . . .
N3 N 0.1648(5) 0.37481(10) 0.3240(3) 0.0477(6) Uani 1 1 d . . . . .
O3 O 1.0142(3) 0.43798(7) 0.63097(19) 0.0443(6) Uani 1 1 d . U . . .
N4 N 0.3888(4) 0.50026(9) 0.1849(2) 0.0473(6) Uani 1 1 d . . . . .
H1N H 0.559400 0.508700 0.246500 0.050 Uiso 1 1 d . . . . .
H2N H 0.280100 0.526200 0.099300 0.050 Uiso 1 1 d . . . . .
C1 C 0.2564(5) 0.45429(11) 0.2097(3) 0.0386(6) Uani 1 1 d . . . . .
C2 C 0.3534(5) 0.41340(10) 0.3399(3) 0.0380(6) Uani 1 1 d . . . . .
C3 C 0.6162(5) 0.41216(10) 0.4749(3) 0.0377(6) Uani 1 1 d . U . . .
C5 C 0.9433(5) 0.38846(10) 0.6798(3) 0.0385(6) Uani 1 1 d . U . . .
N5 N 0.7912(4) 0.45364(9) 0.4916(2) 0.0439(6) Uani 1 1 d . . . . .
C6 C 1.1592(5) 0.36298(11) 0.8259(3) 0.0441(7) Uani 1 1 d . . . . .
C7 C 1.2792(7) 0.28268(14) 0.9965(4) 0.0626(9) Uani 1 1 d . . . . .
H7A H 1.384184 0.308656 1.084756 0.075 Uiso 1 1 calc R . . . .
H7B H 1.175830 0.256702 1.049952 0.075 Uiso 1 1 calc R . . . .
C8 C 1.4752(7) 0.25213(16) 0.9286(4) 0.0703(10) Uani 1 1 d . . . . .
H8A H 1.618405 0.234812 1.021805 0.105 Uiso 1 1 calc GR . . . .
H8B H 1.565819 0.277448 0.867358 0.105 Uiso 1 1 calc GR . . . .
H8C H 1.373599 0.223551 0.850835 0.105 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.196(3) . ?
N1 C3 1.378(3) . ?
N1 C5 1.292(3) . ?
O2 C6 1.321(3) . ?
O2 C7 1.469(3) . ?
O4 N2 1.409(3) . ?
O4 N3 1.365(3) . ?
N2 C1 1.312(3) . ?
N3 C2 1.303(3) . ?
O3 C5 1.343(3) . ?
O3 N5 1.402(2) . ?
N4 H1N 0.8791 . ?
N4 H2N 0.9833 . ?
N4 C1 1.338(3) . ?
C1 C2 1.438(3) . ?
C2 C3 1.454(3) . ?
C3 N5 1.310(3) . ?
C5 C6 1.498(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.454(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
C5 N1 C3 101.1(2) . . ?
C6 O2 C7 116.5(2) . . ?
N3 O4 N2 111.16(17) . . ?
C1 N2 O4 105.19(18) . . ?
C2 N3 O4 105.7(2) . . ?
C5 O3 N5 105.85(17) . . ?
H1N N4 H2N 120.5 . . ?
C1 N4 H1N 122.7 . . ?
C1 N4 H2N 116.6 . . ?
N2 C1 N4 124.2(2) . . ?
N2 C1 C2 108.1(2) . . ?
N4 C1 C2 127.7(2) . . ?
N3 C2 C1 109.9(2) . . ?
N3 C2 C3 121.7(2) . . ?
C1 C2 C3 128.4(2) . . ?
N1 C3 C2 125.4(2) . . ?
N5 C3 N1 115.3(2) . . ?
N5 C3 C2 119.3(2) . . ?
N1 C5 O3 114.6(2) . . ?
N1 C5 C6 130.5(2) . . ?
O3 C5 C6 114.8(2) . . ?
C3 N5 O3 103.01(18) . . ?
O1 C6 O2 127.2(2) . . ?
O1 C6 C5 121.7(2) . . ?
O2 C6 C5 111.0(2) . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 O2 110.6(2) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_SQMONO1_0m_5
_database_code_depnum_ccdc_archive 'CCDC 2281789'
loop_
_audit_author_name
_audit_author_address
'Qi Sun'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-07-16 deposited with the CCDC.	2023-10-17 downloaded from the CCDC.
;
_audit_creation_method           
;
FinalCif by Daniel Kratzert, Freiburg 2019,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C3 H5 N5 O2'
_chemical_formula_moiety         ?
_chemical_formula_weight         143.12
_chemical_melting_point          ?
_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                   7.654(6)
_cell_length_b                   11.714(10)
_cell_length_c                   19.209(15)
_cell_angle_alpha                90
_cell_angle_beta                 96.528(10)
_cell_angle_gamma                90
_cell_volume                     1711(2)
_cell_formula_units_Z            12
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    803
_cell_measurement_theta_min      2.6785
_cell_measurement_theta_max      27.4585
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.415068
_exptl_absorpt_correction_T_max  0.745834
_exptl_absorpt_process_details   
;
TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1: Krause, L.,
Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      296(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           30.0
_diffrn_detector                 CCD
_diffrn_detector_type            'Bruker APEXII'
_diffrn_detector_area_resol_mean 8.3
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 QUAZAR'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            4151
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_theta_min         2.040
_diffrn_reflns_theta_max         29.236
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             4151
_reflns_number_gt                2876
_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 BIS 2014.5.0.0/23-May-2014 && APEX2_2014.7-1'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXTL XT 2018/2'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0645P)²+1.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4151
_refine_ls_number_parameters     275
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0713
_refine_ls_wR_factor_ref         0.1889
_refine_ls_wR_factor_gt          0.1749
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'

_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_
_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_1 C 0.4946(4) 0.4827(2) 0.37057(14) 0.0315(6) Uani 1 1 d . . . . .
N1_1 N 0.9824(4) 0.4309(2) 0.41662(13) 0.0421(6) Uani 1 1 d . . . . .
H1A_1 H 1.084994 0.444503 0.404333 0.051 Uiso 1 1 calc R U . . .
H1B_1 H 0.972054 0.392375 0.454023 0.051 Uiso 1 1 calc R U . . .
C2_1 C 0.8398(4) 0.4696(2) 0.37779(13) 0.0286(6) Uani 1 1 d . . . . .
N2_1 N 0.8323(3) 0.5290(2) 0.31998(12) 0.0330(5) Uani 1 1 d . . . . .
O2_1 O 0.4723(3) 0.3796(2) 0.46177(12) 0.0454(6) Uani 1 1 d . . . . .
C4_1 C 0.6663(4) 0.4458(2) 0.40020(13) 0.0295(6) Uani 1 1 d . . . . .
N4_1 N 0.3775(4) 0.4421(2) 0.40809(14) 0.0409(6) Uani 1 1 d . . . . .
N3_1 N 0.4542(4) 0.5449(2) 0.31094(12) 0.0400(6) Uani 1 1 d . . . . .
H3A_1 H 0.346120 0.559314 0.296166 0.048 Uiso 1 1 calc R U . . .
H3B_1 H 0.536722 0.569784 0.288096 0.048 Uiso 1 1 calc R U . . .
N5_1 N 0.6505(3) 0.3842(2) 0.45531(13) 0.0379(6) Uani 1 1 d . . . . .
O1_1 O 1.0062(3) 0.55078(18) 0.30302(10) 0.0367(5) Uani 1 1 d . . . . .
H1_1 H 1.001565 0.573413 0.262450 0.055 Uiso 1 1 calc DR U . . .
C1_2 C -0.1858(4) 0.8253(2) 0.36156(15) 0.0344(6) Uani 1 1 d . . . . .
N1_2 N 0.3006(4) 0.7674(2) 0.40909(13) 0.0438(7) Uani 1 1 d . . . . .
H1A_2 H 0.403635 0.779573 0.396821 0.053 Uiso 1 1 calc R U . . .
H1B_2 H 0.288758 0.726725 0.445529 0.053 Uiso 1 1 calc R U . . .
C2_2 C 0.1594(4) 0.8115(2) 0.37162(13) 0.0287(6) Uani 1 1 d . . . . .
N2_2 N 0.1531(3) 0.8743(2) 0.31572(12) 0.0326(5) Uani 1 1 d . . . . .
O2_2 O -0.2135(3) 0.7202(2) 0.45188(12) 0.0459(6) Uani 1 1 d . . . . .
C4_2 C -0.0168(4) 0.7873(2) 0.39278(14) 0.0307(6) Uani 1 1 d . . . . .
N4_2 N -0.3062(4) 0.7841(2) 0.39809(15) 0.0431(6) Uani 1 1 d . . . . .
N3_2 N -0.2205(4) 0.8889(2) 0.30275(13) 0.0435(7) Uani 1 1 d . . . . .
H3A_2 H -0.327485 0.904622 0.287016 0.052 Uiso 1 1 calc R U . . .
H3B_2 H -0.135583 0.913443 0.281117 0.052 Uiso 1 1 calc R U . . .
N5_2 N -0.0349(3) 0.7242(2) 0.44695(13) 0.0375(6) Uani 1 1 d . . . . .
O1_2 O 0.3278(3) 0.89400(17) 0.29802(10) 0.0358(5) Uani 1 1 d . . . . .
H1_2 H 0.323062 0.932656 0.262261 0.054 Uiso 1 1 calc DR U . . .
C1_3 C 0.8512(4) 0.6541(2) 0.13193(14) 0.0321(6) Uani 1 1 d . . . . .
N1_3 N 0.3644(4) 0.5963(2) 0.08823(14) 0.0444(7) Uani 1 1 d . . . . .
H1A_3 H 0.261379 0.608442 0.100481 0.053 Uiso 1 1 calc R U . . .
H1B_3 H 0.376281 0.556064 0.051612 0.053 Uiso 1 1 calc R U . . .
O1_3 O 0.3333(3) 0.71712(19) 0.19888(11) 0.0409(5) Uani 1 1 d . . . . .
H1_3 H 0.334011 0.758275 0.233443 0.061 Uiso 1 1 calc DR U . . .
C2_3 C 0.5063(4) 0.6400(2) 0.12618(14) 0.0310(6) Uani 1 1 d . . . . .
N2_3 N 0.5096(3) 0.7019(2) 0.18235(12) 0.0352(6) Uani 1 1 d . . . . .
O2_3 O 0.8707(3) 0.5554(2) 0.03910(12) 0.0458(6) Uani 1 1 d . . . . .
C3_3 C 0.6796(4) 0.6177(2) 0.10295(14) 0.0301(6) Uani 1 1 d . . . . .
N3_3 N 0.8969(4) 0.7138(2) 0.19294(12) 0.0397(6) Uani 1 1 d . . . . .
H3A_3 H 1.005740 0.727262 0.206811 0.048 Uiso 1 1 calc DR U . . .
H3B_3 H 0.816507 0.737800 0.217214 0.048 Uiso 1 1 calc R U . . .
N4_3 N 0.9669(4) 0.6157(2) 0.09310(14) 0.0415(6) Uani 1 1 d . . . . .
N5_3 N 0.6932(3) 0.5579(2) 0.04714(13) 0.0384(6) Uani 1 1 d . . . . .


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_1 N4_1 1.302(4) . ?
C1_1 N3_1 1.363(4) . ?
C1_1 C4_1 1.438(4) . ?
N1_1 C2_1 1.329(4) . ?
C2_1 N2_1 1.306(3) . ?
C2_1 C4_1 1.469(4) . ?
N2_1 O1_1 1.429(3) . ?
O2_1 N5_1 1.384(4) . ?
O2_1 N4_1 1.398(3) . ?
C4_1 N5_1 1.298(4) . ?
C1_2 N4_2 1.312(4) . ?
C1_2 N3_2 1.354(4) . ?
C1_2 C4_2 1.434(4) . ?
N1_2 C2_2 1.333(4) . ?
C2_2 N2_2 1.298(3) . ?
C2_2 C4_2 1.479(4) . ?
N2_2 O1_2 1.435(3) . ?
O2_2 N5_2 1.382(4) . ?
O2_2 N4_2 1.402(3) . ?
C4_2 N5_2 1.297(4) . ?
C1_3 N4_3 1.300(4) . ?
C1_3 N3_3 1.376(4) . ?
C1_3 C3_3 1.432(4) . ?
N1_3 C2_3 1.339(4) . ?
O1_3 N2_3 1.432(3) . ?
C2_3 N2_3 1.298(4) . ?
C2_3 C3_3 1.470(4) . ?
O2_3 N5_3 1.385(4) . ?
O2_3 N4_3 1.394(3) . ?
C3_3 N5_3 1.295(4) . ?

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_1 C1_1 N3_1 123.8(3) . . ?
N4_1 C1_1 C4_1 109.0(2) . . ?
N3_1 C1_1 C4_1 127.1(3) . . ?
N2_1 C2_1 N1_1 127.8(3) . . ?
N2_1 C2_1 C4_1 113.4(2) . . ?
N1_1 C2_1 C4_1 118.9(2) . . ?
C2_1 N2_1 O1_1 109.7(2) . . ?
N5_1 O2_1 N4_1 110.3(2) . . ?
N5_1 C4_1 C1_1 108.9(3) . . ?
N5_1 C4_1 C2_1 121.0(3) . . ?
C1_1 C4_1 C2_1 130.0(2) . . ?
C1_1 N4_1 O2_1 105.5(2) . . ?
C4_1 N5_1 O2_1 106.2(2) . . ?
N4_2 C1_2 N3_2 124.4(3) . . ?
N4_2 C1_2 C4_2 108.5(3) . . ?
N3_2 C1_2 C4_2 127.0(3) . . ?
N2_2 C2_2 N1_2 128.2(3) . . ?
N2_2 C2_2 C4_2 112.8(2) . . ?
N1_2 C2_2 C4_2 119.0(2) . . ?
C2_2 N2_2 O1_2 109.8(2) . . ?
N5_2 O2_2 N4_2 110.7(2) . . ?
N5_2 C4_2 C1_2 109.8(3) . . ?
N5_2 C4_2 C2_2 120.9(2) . . ?
C1_2 C4_2 C2_2 129.2(3) . . ?
C1_2 N4_2 O2_2 105.3(2) . . ?
C4_2 N5_2 O2_2 105.7(2) . . ?
N4_3 C1_3 N3_3 122.7(3) . . ?
N4_3 C1_3 C3_3 109.2(2) . . ?
N3_3 C1_3 C3_3 128.0(3) . . ?
N2_3 C2_3 N1_3 127.2(3) . . ?
N2_3 C2_3 C3_3 114.8(3) . . ?
N1_3 C2_3 C3_3 118.1(3) . . ?
C2_3 N2_3 O1_3 108.9(2) . . ?
N5_3 O2_3 N4_3 110.4(2) . . ?
N5_3 C3_3 C1_3 109.0(3) . . ?
N5_3 C3_3 C2_3 120.5(3) . . ?
C1_3 C3_3 C2_3 130.5(2) . . ?
C1_3 N4_3 O2_3 105.4(2) . . ?
C3_3 N5_3 O2_3 106.0(2) . . ?

####################################################################### 
# 
# 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_jzy316_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2281792'
loop_
_audit_author_name
_audit_author_address
'Qi Sun'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-07-16 deposited with the CCDC.	2023-10-17 downloaded from the CCDC.
;
_audit_creation_date             2021-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H7 N O, C6 H4 N8 O3'
_chemical_formula_sum            'C9 H11 N9 O4'
_chemical_formula_weight         309.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1101(7)
_cell_length_b                   8.0905(10)
_cell_length_c                   13.8354(17)
_cell_angle_alpha                100.725(4)
_cell_angle_beta                 94.384(4)
_cell_angle_gamma                99.483(4)
_cell_volume                     658.75(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7699
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      54.914
_cell_measurement_theta_min      4.923
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1697 before and 0.0562 after correction. The Ratio of minimum to maximum transmission is 0.7439. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9483
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.950
_diffrn_reflns_theta_min         4.923
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2274
_reflns_number_total             2444
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       0.060(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2444
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0981
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+9.4463P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2972
_refine_ls_wR_factor_ref         0.2980
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C20(H20)
2.b X=CH2 refined with riding coordinates:
 N4(H4A,H4B), N9(H9A,H9B)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
N1 N 0.4218(9) 0.6014(7) 0.8783(4) 0.0295(14) Uani 1 1 d . . . . .
N2 N 0.9247(10) -0.0214(8) 0.1303(4) 0.0308(14) Uani 1 1 d . . . . .
N3 N 1.2087(10) -0.1719(8) 0.1388(4) 0.0298(14) Uani 1 1 d . . . . .
N4 N 1.2488(10) -0.1661(8) 0.3091(4) 0.0292(14) Uani 1 1 d . . . . .
H4A H 1.361477 -0.221139 0.303910 0.035 Uiso 1 1 calc R . . . .
H4B H 1.202505 -0.135172 0.367343 0.035 Uiso 1 1 calc R . . . .
N5 N 0.8858(9) 0.0106(7) 0.3899(4) 0.0260(13) Uani 1 1 d . . . . .
N6 N 0.6819(9) 0.1288(7) 0.2862(4) 0.0244(12) Uani 1 1 d . . . . .
N8 N 0.1785(9) 0.3898(7) 0.4233(4) 0.0271(13) Uani 1 1 d . . . . .
N7 N 0.3149(9) 0.3181(7) 0.3570(4) 0.0273(13) Uani 1 1 d . . . . .
N9 N 0.1580(9) 0.3984(7) 0.5950(4) 0.0284(13) Uani 1 1 d . . . . .
H9A H 0.046700 0.454994 0.598755 0.034 Uiso 1 1 calc R . . . .
H9B H 0.215331 0.368643 0.648112 0.034 Uiso 1 1 calc R . . . .
O10 O 0.4138(8) 0.3590(6) 0.7624(4) 0.0328(12) Uani 1 1 d . . . . .
O11 O 0.4109(7) 0.2689(6) 0.5057(3) 0.0254(11) Uani 1 1 d . . . . .
O12 O 0.7338(7) 0.0962(6) 0.4420(3) 0.0252(11) Uani 1 1 d . . . . .
O13 O 1.0683(8) -0.1036(7) 0.0776(3) 0.0323(12) Uani 1 1 d . . . . .
C14 C 1.1480(11) -0.1294(8) 0.2287(5) 0.0254(14) Uani 1 1 d . . . . .
C15 C 0.9697(11) -0.0348(8) 0.2217(5) 0.0239(14) Uani 1 1 d . . . . .
C16 C 0.8466(10) 0.0355(8) 0.3006(5) 0.0234(14) Uani 1 1 d . . . . .
C17 C 0.6219(10) 0.1596(8) 0.3753(5) 0.0222(14) Uani 1 1 d . . . . .
C18 C 0.4449(10) 0.2500(8) 0.4073(5) 0.0246(14) Uani 1 1 d . . . . .
C19 C 0.2395(10) 0.3578(8) 0.5092(5) 0.0219(14) Uani 1 1 d . . . . .
C20 C 0.5156(11) 0.4897(9) 0.8209(5) 0.0284(15) Uani 1 1 d . . . . .
H20 H 0.673892 0.511079 0.824592 0.034 Uiso 1 1 calc R . . . .
C21 C 0.5544(15) 0.7584(11) 0.9396(7) 0.049(2) Uani 1 1 d . . . . .
H21A H 0.713535 0.756742 0.935660 0.074 Uiso 1 1 calc GR . . . .
H21B H 0.522670 0.765724 1.008493 0.074 Uiso 1 1 calc GR . . . .
H21C H 0.515869 0.857773 0.915735 0.074 Uiso 1 1 calc GR . . . .
C22 C 0.1837(12) 0.5814(10) 0.8765(7) 0.042(2) Uani 1 1 d . . . . .
H22A H 0.132691 0.676672 0.852478 0.063 Uiso 1 1 calc GR . . . .
H22B H 0.142262 0.580584 0.943482 0.063 Uiso 1 1 calc GR . . . .
H22C H 0.113452 0.473233 0.832338 0.063 Uiso 1 1 calc GR . . . .


_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
N1 C20 1.323(9) . ?
N1 C21 1.464(9) . ?
N1 C22 1.435(9) . ?
N2 O13 1.361(7) . ?
N2 C15 1.302(9) . ?
N3 O13 1.407(7) . ?
N3 C14 1.325(8) . ?
N4 C14 1.336(9) . ?
N5 O12 1.411(6) . ?
N5 C16 1.300(8) . ?
N6 C16 1.378(8) . ?
N6 C17 1.304(8) . ?
N8 N7 1.397(7) . ?
N8 C19 1.303(8) . ?
N7 C18 1.274(9) . ?
N9 C19 1.328(8) . ?
O10 C20 1.244(8) . ?
O11 C18 1.376(8) . ?
O11 C19 1.364(7) . ?
O12 C17 1.333(7) . ?
C14 C15 1.438(9) . ?
C15 C16 1.454(9) . ?
C17 C18 1.453(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
C20 N1 C21 121.6(6) . . ?
C20 N1 C22 121.2(6) . . ?
C22 N1 C21 117.0(6) . . ?
C15 N2 O13 106.1(5) . . ?
C14 N3 O13 104.9(5) . . ?
C16 N5 O12 103.0(5) . . ?
C17 N6 C16 100.4(5) . . ?
C19 N8 N7 106.7(5) . . ?
C18 N7 N8 105.9(5) . . ?
C19 O11 C18 101.4(5) . . ?
C17 O12 N5 105.6(5) . . ?
N2 O13 N3 111.4(5) . . ?
N3 C14 N4 123.3(6) . . ?
N3 C14 C15 107.9(6) . . ?
N4 C14 C15 128.8(6) . . ?
N2 C15 C14 109.8(6) . . ?
N2 C15 C16 122.2(6) . . ?
C14 C15 C16 128.0(6) . . ?
N5 C16 N6 116.0(6) . . ?
N5 C16 C15 120.8(6) . . ?
N6 C16 C15 123.2(6) . . ?
N6 C17 O12 115.0(5) . . ?
N6 C17 C18 127.0(6) . . ?
O12 C17 C18 118.0(5) . . ?
N7 C18 O11 113.8(5) . . ?
N7 C18 C17 129.0(6) . . ?
O11 C18 C17 117.2(6) . . ?
N8 C19 N9 129.2(6) . . ?
N8 C19 O11 112.1(5) . . ?
N9 C19 O11 118.6(5) . . ?
O10 C20 N1 125.5(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_SQSAN7
_database_code_depnum_ccdc_archive 'CCDC 2281791'
loop_
_audit_author_name
_audit_author_address
'Qi Sun'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-07-16 deposited with the CCDC.	2023-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H5 N7 O3'
_chemical_formula_weight         211.16

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

_cell_length_a                   17.065(17)
_cell_length_b                   12.243(12)
_cell_length_c                   4.006(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     837.0(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    626
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      16.99

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      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            7395
_diffrn_reflns_av_unetI/netI     0.0957
_diffrn_reflns_av_R_equivalents  0.0896
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.047
_diffrn_reflns_theta_max         27.562
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1922
_reflns_number_gt                983
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.989

_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-2016/6 (Sheldrick, 2016)'
_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)+(0.0200P)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 294 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.5(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1922
_refine_ls_number_parameters     144
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1015
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.56260(18) 0.2610(3) 0.3452(10) 0.0563(10) Uani 1 1 d . . . . .
O2 O 0.46216(16) 0.4303(2) 0.2122(10) 0.0498(9) Uani 1 1 d . . . . .
O3 O 0.16330(16) 0.5404(3) 0.6960(12) 0.0643(10) Uani 1 1 d . . . . .
N1 N 0.5160(3) 0.0951(4) 0.7812(15) 0.0583(14) Uani 1 1 d . . . . .
N2 N 0.4703(2) 0.1846(3) 0.6736(13) 0.0498(11) Uani 1 1 d . . . . .
H2 H 0.422700 0.189652 0.741879 0.060 Uiso 1 1 calc R U . . .
N3 N 0.3723(2) 0.3642(3) 0.5492(11) 0.0443(11) Uani 1 1 d . . . . .
N5 N 0.2242(2) 0.4684(3) 0.6715(15) 0.0597(13) Uani 1 1 d . . . . .
N6 N 0.1800(2) 0.6377(3) 0.5259(11) 0.0510(12) Uani 1 1 d . . . . .
N7 N 0.2879(2) 0.6982(3) 0.2220(15) 0.0620(13) Uani 1 1 d . . . . .
H7A H 0.266056 0.760050 0.181467 0.074 Uiso 1 1 calc R U . . .
H7B H 0.334086 0.684697 0.146216 0.074 Uiso 1 1 calc R U . . .
N8 N 0.40064(19) 0.5069(3) 0.2128(14) 0.0508(11) Uani 1 1 d . . . . .
C1 C 0.4979(3) 0.2604(3) 0.4727(13) 0.0422(13) Uani 1 1 d . . . . .
C2 C 0.4404(3) 0.3504(4) 0.4163(13) 0.0407(12) Uani 1 1 d . . . . .
C3 C 0.3507(3) 0.4627(3) 0.4171(13) 0.0418(13) Uani 1 1 d . . . . .
C4 C 0.2767(3) 0.5169(3) 0.4955(14) 0.0426(13) Uani 1 1 d . . . . .
C5 C 0.2504(3) 0.6234(4) 0.4016(13) 0.0444(13) Uani 1 1 d . . . . .
H1A H 0.519(3) 0.055(4) 0.604(14) 0.062(19) Uiso 1 1 d . . . . .
H1B H 0.565(3) 0.126(4) 0.868(14) 0.08(2) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.217(5) . ?
O2 C2 1.327(5) . ?
O2 N8 1.408(4) . ?
O3 N5 1.367(4) . ?
O3 N6 1.401(5) . ?
N1 N2 1.412(5) . ?
N1 H1A 0.86(5) . ?
N1 H1B 0.98(5) . ?
N2 C1 1.316(6) . ?
N2 H2 0.8600 . ?
N3 C2 1.290(6) . ?
N3 C3 1.368(5) . ?
N5 C4 1.286(6) . ?
N6 C5 1.313(5) . ?
N7 C5 1.329(6) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N8 C3 1.299(6) . ?
C1 C2 1.492(6) . ?
C3 C4 1.461(6) . ?
C4 C5 1.429(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 N8 106.4(3) . . ?
N5 O3 N6 111.1(3) . . ?
N2 N1 H1A 103(3) . . ?
N2 N1 H1B 106(3) . . ?
H1A N1 H1B 117(5) . . ?
C1 N2 N1 122.5(4) . . ?
C1 N2 H2 118.8 . . ?
N1 N2 H2 118.8 . . ?
C2 N3 C3 101.4(4) . . ?
C4 N5 O3 105.7(4) . . ?
C5 N6 O3 104.9(4) . . ?
C5 N7 H7A 120.0 . . ?
C5 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C3 N8 O2 102.3(4) . . ?
O1 C1 N2 125.8(4) . . ?
O1 C1 C2 121.9(5) . . ?
N2 C1 C2 112.3(4) . . ?
N3 C2 O2 114.2(4) . . ?
N3 C2 C1 128.8(5) . . ?
O2 C2 C1 117.0(4) . . ?
N8 C3 N3 115.7(4) . . ?
N8 C3 C4 120.9(4) . . ?
N3 C3 C4 123.4(4) . . ?
N5 C4 C5 110.3(4) . . ?
N5 C4 C3 120.7(4) . . ?
C5 C4 C3 129.0(4) . . ?
N6 C5 N7 123.7(4) . . ?
N6 C5 C4 108.0(4) . . ?
N7 C5 C4 128.3(4) . . ?

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
N6 O3 N5 C4 0.0(5) . . . . ?
N5 O3 N6 C5 -0.1(5) . . . . ?
C2 O2 N8 C3 0.1(5) . . . . ?
N1 N2 C1 O1 3.6(8) . . . . ?
N1 N2 C1 C2 -175.7(5) . . . . ?
C3 N3 C2 O2 -0.9(5) . . . . ?
C3 N3 C2 C1 176.4(5) . . . . ?
N8 O2 C2 N3 0.5(5) . . . . ?
N8 O2 C2 C1 -177.1(4) . . . . ?
O1 C1 C2 N3 -175.3(5) . . . . ?
N2 C1 C2 N3 3.9(7) . . . . ?
O1 C1 C2 O2 1.9(7) . . . . ?
N2 C1 C2 O2 -178.9(4) . . . . ?
O2 N8 C3 N3 -0.7(6) . . . . ?
O2 N8 C3 C4 179.3(4) . . . . ?
C2 N3 C3 N8 1.0(6) . . . . ?
C2 N3 C3 C4 -179.1(4) . . . . ?
O3 N5 C4 C5 0.1(6) . . . . ?
O3 N5 C4 C3 -179.7(4) . . . . ?
N8 C3 C4 N5 173.2(5) . . . . ?
N3 C3 C4 N5 -6.8(7) . . . . ?
N8 C3 C4 C5 -6.7(8) . . . . ?
N3 C3 C4 C5 173.4(5) . . . . ?
O3 N6 C5 N7 -179.7(5) . . . . ?
O3 N6 C5 C4 0.2(5) . . . . ?
N5 C4 C5 N6 -0.2(6) . . . . ?
C3 C4 C5 N6 179.6(5) . . . . ?
N5 C4 C5 N7 179.6(5) . . . . ?
C3 C4 C5 N7 -0.5(9) . . . . ?

_refine_diff_density_max         0.154
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.047



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

data_2_a
_database_code_depnum_ccdc_archive 'CCDC 2281793'
loop_
_audit_author_name
_audit_author_address
'Qi Sun'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-07-16 deposited with the CCDC.	2023-10-17 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            'C6 H2 N10 O3'
_chemical_formula_weight         262.18

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      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                   4.4199(13)
_cell_length_b                   7.132(2)
_cell_length_c                   16.288(5)
_cell_angle_alpha                81.681(7)
_cell_angle_beta                 87.434(7)
_cell_angle_gamma                76.836(7)
_cell_volume                     494.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1795
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      20.56

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.147
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.988
_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            11869
_diffrn_reflns_av_unetI/netI     0.1009
_diffrn_reflns_av_R_equivalents  0.1115
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.962
_diffrn_reflns_theta_max         25.116
_diffrn_reflns_theta_full        25.116
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1750
_reflns_number_gt                825
_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)+(0.0872P)²+0.0968P] 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         1750
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1628
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.1717
_refine_ls_wR_factor_gt          0.1225
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_restrained_S_all      0.938
_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 0.6130(10) -0.1332(6) 0.8696(3) 0.0583(11) Uani 1 1 d . . . . .
C2 C 0.5773(9) -0.0092(6) 0.7927(2) 0.0561(11) Uani 1 1 d . . . . .
C3 C 0.6947(9) 0.1635(6) 0.7658(2) 0.0537(11) Uani 1 1 d . . . . .
C4 C 0.7986(9) 0.4055(6) 0.6942(2) 0.0540(11) Uani 1 1 d . . . . .
C5 C 0.8478(9) 0.5632(6) 0.6348(2) 0.0539(11) Uani 1 1 d . . . . .
C6 C 0.8159(9) 0.7589(5) 0.5230(3) 0.0516(11) Uani 1 1 d . . . . .
N1 N 0.7997(13) -0.3407(7) 1.0556(3) 0.1132(18) Uani 1 1 d . . . . .
N2 N 0.7769(10) -0.2358(6) 0.9972(3) 0.0796(12) Uani 1 1 d . . . . .
N3 N 0.7707(9) -0.1044(5) 0.9370(2) 0.0699(11) Uani 1 1 d . . . . .
N4 N 0.4726(9) -0.2729(5) 0.8682(2) 0.0719(11) Uani 1 1 d . . . . .
N5 N 0.4144(8) -0.0773(5) 0.7438(2) 0.0691(11) Uani 1 1 d . . . . .
N6 N 0.6505(7) 0.2711(5) 0.6887(2) 0.0547(9) Uani 1 1 d . . . . .
N7 N 0.8541(9) 0.2262(5) 0.8165(2) 0.0668(10) Uani 1 1 d . . . . .
N8 N 1.0080(9) 0.6876(5) 0.6457(2) 0.0689(11) Uani 1 1 d . . . . .
N9 N 0.9888(8) 0.8159(5) 0.5728(2) 0.0658(11) Uani 1 1 d . . . . .
N10 N 0.7373(8) 0.8342(5) 0.4465(2) 0.0647(10) Uani 1 1 d . . . . .
H10A H 0.8022 0.9342 0.4233 0.078 Uiso 1 1 calc R U . . .
H10B H 0.6208 0.7835 0.4195 0.078 Uiso 1 1 calc R U . . .
O1 O 0.3472(7) -0.2396(4) 0.78909(19) 0.0807(10) Uani 1 1 d . . . . .
O2 O 0.9290(7) 0.3903(4) 0.76847(17) 0.0702(9) Uani 1 1 d . . . . .
O3 O 0.7173(6) 0.5984(4) 0.55840(15) 0.0556(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N4 1.291(5) . ?
C1 N3 1.390(5) . ?
C1 C2 1.419(5) . ?
C2 N5 1.308(5) . ?
C2 C3 1.447(5) . ?
C3 N7 1.297(5) . ?
C3 N6 1.370(5) . ?
C4 N6 1.293(5) . ?
C4 O2 1.343(4) . ?
C4 C5 1.423(5) . ?
C5 N8 1.289(5) . ?
C5 O3 1.362(4) . ?
C6 N9 1.304(5) . ?
C6 N10 1.312(5) . ?
C6 O3 1.359(4) . ?
N1 N2 1.114(5) . ?
N2 N3 1.251(5) . ?
N4 O1 1.393(4) . ?
N5 O1 1.365(4) . ?
N7 O2 1.407(4) . ?
N8 N9 1.384(5) . ?
N10 H10A 0.8600 . ?
N10 H10B 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
N4 C1 N3 125.4(4) . . ?
N4 C1 C2 110.1(4) . . ?
N3 C1 C2 124.4(4) . . ?
N5 C2 C1 108.4(4) . . ?
N5 C2 C3 121.8(4) . . ?
C1 C2 C3 129.7(4) . . ?
N7 C3 N6 115.5(4) . . ?
N7 C3 C2 119.7(4) . . ?
N6 C3 C2 124.8(4) . . ?
N6 C4 O2 113.6(3) . . ?
N6 C4 C5 130.8(4) . . ?
O2 C4 C5 115.6(3) . . ?
N8 C5 O3 112.8(3) . . ?
N8 C5 C4 126.1(4) . . ?
O3 C5 C4 121.1(3) . . ?
N9 C6 N10 128.4(4) . . ?
N9 C6 O3 112.1(3) . . ?
N10 C6 O3 119.5(4) . . ?
N1 N2 N3 171.9(5) . . ?
N2 N3 C1 112.6(4) . . ?
C1 N4 O1 104.5(3) . . ?
C2 N5 O1 105.6(3) . . ?
C4 N6 C3 101.9(3) . . ?
C3 N7 O2 102.9(3) . . ?
C5 N8 N9 106.4(3) . . ?
C6 N9 N8 106.4(3) . . ?
C6 N10 H10A 120.0 . . ?
C6 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
N5 O1 N4 111.3(3) . . ?
C4 O2 N7 106.1(3) . . ?
C6 O3 C5 102.2(3) . . ?

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 -0.6(5) . . . . ?
N3 C1 C2 N5 -179.3(4) . . . . ?
N4 C1 C2 C3 -179.6(4) . . . . ?
N3 C1 C2 C3 1.8(7) . . . . ?
N5 C2 C3 N7 179.7(4) . . . . ?
C1 C2 C3 N7 -1.4(7) . . . . ?
N5 C2 C3 N6 -0.2(6) . . . . ?
C1 C2 C3 N6 178.7(4) . . . . ?
N6 C4 C5 N8 -177.9(4) . . . . ?
O2 C4 C5 N8 1.3(6) . . . . ?
N6 C4 C5 O3 3.4(7) . . . . ?
O2 C4 C5 O3 -177.4(3) . . . . ?
N4 C1 N3 N2 3.1(6) . . . . ?
C2 C1 N3 N2 -178.4(4) . . . . ?
N3 C1 N4 O1 179.1(4) . . . . ?
C2 C1 N4 O1 0.5(5) . . . . ?
C1 C2 N5 O1 0.4(4) . . . . ?
C3 C2 N5 O1 179.5(4) . . . . ?
O2 C4 N6 C3 -0.3(4) . . . . ?
C5 C4 N6 C3 178.8(4) . . . . ?
N7 C3 N6 C4 0.9(5) . . . . ?
C2 C3 N6 C4 -179.2(4) . . . . ?
N6 C3 N7 O2 -1.0(5) . . . . ?
C2 C3 N7 O2 179.1(3) . . . . ?
O3 C5 N8 N9 -0.2(5) . . . . ?
C4 C5 N8 N9 -179.0(4) . . . . ?
N10 C6 N9 N8 -178.8(4) . . . . ?
O3 C6 N9 N8 -0.1(4) . . . . ?
C5 N8 N9 C6 0.2(5) . . . . ?
C2 N5 O1 N4 -0.1(4) . . . . ?
C1 N4 O1 N5 -0.2(4) . . . . ?
N6 C4 O2 N7 -0.2(5) . . . . ?
C5 C4 O2 N7 -179.5(3) . . . . ?
C3 N7 O2 C4 0.7(4) . . . . ?
N9 C6 O3 C5 -0.1(4) . . . . ?
N10 C6 O3 C5 178.8(3) . . . . ?
N8 C5 O3 C6 0.2(4) . . . . ?
C4 C5 O3 C6 179.0(4) . . . . ?

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.241
_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_WQ20200513_1_a
_database_code_depnum_ccdc_archive 'CCDC 2281797'
loop_
_audit_author_name
_audit_author_address
'Qi Sun'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-07-16 deposited with the CCDC.	2023-10-17 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 H2 N8 O5'
_chemical_formula_sum            'C6 H2 N8 O5'
_chemical_formula_weight         266.16

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   7.2609(5)
_cell_length_b                   18.6033(12)
_cell_length_c                   7.3808(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.583(2)
_cell_angle_gamma                90
_cell_volume                     990.40(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4015
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      26.03

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.157
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6727
_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_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            9918
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.986
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2249
_reflns_number_gt                1582
_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)+(0.0423P)²+0.2704P] 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       0.048(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2249
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.0304(3) 0.78387(10) 0.7257(2) 0.0500(5) Uani 1 1 d . . . . .
C2 C 0.0173(2) 0.70970(10) 0.7626(2) 0.0464(4) Uani 1 1 d . . . . .
C3 C 0.1602(2) 0.65378(9) 0.7762(2) 0.0419(4) Uani 1 1 d . . . . .
C4 C 0.3893(2) 0.59548(9) 0.7273(2) 0.0403(4) Uani 1 1 d . . . . .
C5 C 0.5553(2) 0.56594(9) 0.6662(2) 0.0398(4) Uani 1 1 d . . . . .
C6 C 0.7970(2) 0.50237(9) 0.6709(2) 0.0417(4) Uani 1 1 d . . . . .
N1 N -0.1288(3) 0.81429(10) 0.7186(3) 0.0712(6) Uani 1 1 d . . . . .
N2 N -0.1545(2) 0.69520(10) 0.7785(3) 0.0671(5) Uani 1 1 d . . . . .
N3 N 0.3021(2) 0.65314(8) 0.67015(19) 0.0452(4) Uani 1 1 d . . . . .
N4 N 0.1580(2) 0.60102(9) 0.8911(2) 0.0517(4) Uani 1 1 d . . . . .
N5 N 0.6276(2) 0.58314(8) 0.5223(2) 0.0471(4) Uani 1 1 d . . . . .
N6 N 0.7872(2) 0.54183(8) 0.5229(2) 0.0486(4) Uani 1 1 d . . . . .
N7 N 0.9225(2) 0.45494(8) 0.7300(2) 0.0569(5) Uani 1 1 d . . . . .
H7A H 1.013978 0.446411 0.668756 0.068 Uiso 1 1 calc R U . . .
H7B H 0.913610 0.432263 0.830171 0.068 Uiso 1 1 calc R U . . .
N8 N 0.1946(3) 0.82616(10) 0.7066(3) 0.0621(5) Uani 1 1 d . . . . .
O1 O -0.2468(2) 0.75998(10) 0.7515(2) 0.0809(5) Uani 1 1 d . . . . .
O2 O 0.31364(17) 0.56089(6) 0.85911(17) 0.0512(4) Uani 1 1 d . . . . .
O3 O 0.65272(16) 0.51477(6) 0.76853(15) 0.0443(3) Uani 1 1 d . . . . .
O4 O 0.1783(3) 0.87848(10) 0.6089(3) 0.0960(6) Uani 1 1 d . . . . .
O5 O 0.3359(2) 0.80571(8) 0.7959(3) 0.0814(5) 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 1.282(3) . ?
C1 C2 1.412(3) . ?
C1 N8 1.449(3) . ?
C2 N2 1.295(2) . ?
C2 C3 1.464(2) . ?
C3 N4 1.298(2) . ?
C3 N3 1.364(2) . ?
C4 N3 1.292(2) . ?
C4 O2 1.3357(19) . ?
C4 C5 1.443(2) . ?
C5 N5 1.279(2) . ?
C5 O3 1.362(2) . ?
C6 N7 1.307(2) . ?
C6 N6 1.311(2) . ?
C6 O3 1.3576(19) . ?
N1 O1 1.364(2) . ?
N2 O1 1.382(2) . ?
N4 O2 1.3967(18) . ?
N5 N6 1.390(2) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N8 O4 1.209(2) . ?
N8 O5 1.216(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 C2 111.05(18) . . ?
N1 C1 N8 120.27(19) . . ?
C2 C1 N8 128.58(17) . . ?
N2 C2 C1 107.92(17) . . ?
N2 C2 C3 121.88(18) . . ?
C1 C2 C3 130.16(16) . . ?
N4 C3 N3 115.77(16) . . ?
N4 C3 C2 121.36(16) . . ?
N3 C3 C2 122.87(16) . . ?
N3 C4 O2 114.26(14) . . ?
N3 C4 C5 127.57(15) . . ?
O2 C4 C5 118.17(15) . . ?
N5 C5 O3 113.51(14) . . ?
N5 C5 C4 126.99(16) . . ?
O3 C5 C4 119.50(14) . . ?
N7 C6 N6 128.70(16) . . ?
N7 C6 O3 119.23(15) . . ?
N6 C6 O3 112.07(15) . . ?
C1 N1 O1 104.31(17) . . ?
C2 N2 O1 105.16(17) . . ?
C4 N3 C3 101.19(14) . . ?
C3 N4 O2 102.90(13) . . ?
C5 N5 N6 106.28(14) . . ?
C6 N6 N5 106.13(13) . . ?
C6 N7 H7A 120.0 . . ?
C6 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
O4 N8 O5 126.4(2) . . ?
O4 N8 C1 118.0(2) . . ?
O5 N8 C1 115.50(18) . . ?
N1 O1 N2 111.56(14) . . ?
C4 O2 N4 105.88(13) . . ?
C6 O3 C5 102.00(12) . . ?

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 N2 -0.1(2) . . . . ?
N8 C1 C2 N2 176.38(19) . . . . ?
N1 C1 C2 C3 177.54(18) . . . . ?
N8 C1 C2 C3 -5.9(3) . . . . ?
N2 C2 C3 N4 -37.5(3) . . . . ?
C1 C2 C3 N4 145.1(2) . . . . ?
N2 C2 C3 N3 142.13(19) . . . . ?
C1 C2 C3 N3 -35.3(3) . . . . ?
N3 C4 C5 N5 -14.2(3) . . . . ?
O2 C4 C5 N5 166.22(17) . . . . ?
N3 C4 C5 O3 164.75(16) . . . . ?
O2 C4 C5 O3 -14.8(2) . . . . ?
C2 C1 N1 O1 0.2(2) . . . . ?
N8 C1 N1 O1 -176.69(16) . . . . ?
C1 C2 N2 O1 0.0(2) . . . . ?
C3 C2 N2 O1 -177.86(16) . . . . ?
O2 C4 N3 C3 -0.13(19) . . . . ?
C5 C4 N3 C3 -179.68(17) . . . . ?
N4 C3 N3 C4 0.1(2) . . . . ?
C2 C3 N3 C4 -179.51(16) . . . . ?
N3 C3 N4 O2 -0.1(2) . . . . ?
C2 C3 N4 O2 179.58(15) . . . . ?
O3 C5 N5 N6 -0.4(2) . . . . ?
C4 C5 N5 N6 178.68(16) . . . . ?
N7 C6 N6 N5 179.76(18) . . . . ?
O3 C6 N6 N5 0.24(19) . . . . ?
C5 N5 N6 C6 0.07(19) . . . . ?
N1 C1 N8 O4 -32.6(3) . . . . ?
C2 C1 N8 O4 151.2(2) . . . . ?
N1 C1 N8 O5 145.7(2) . . . . ?
C2 C1 N8 O5 -30.5(3) . . . . ?
C1 N1 O1 N2 -0.1(2) . . . . ?
C2 N2 O1 N1 0.0(2) . . . . ?
N3 C4 O2 N4 0.10(19) . . . . ?
C5 C4 O2 N4 179.70(15) . . . . ?
C3 N4 O2 C4 -0.03(17) . . . . ?
N7 C6 O3 C5 180.00(16) . . . . ?
N6 C6 O3 C5 -0.44(19) . . . . ?
N5 C5 O3 C6 0.50(19) . . . . ?
C4 C5 O3 C6 -178.63(15) . . . . ?

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
N7 H7B N4 0.86 2.27 3.102(2) 164.2 3_667 yes
N7 H7A N6 0.86 2.14 2.972(2) 161.2 3_766 yes

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.037



####################################################################### 
# 
# 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 2281796'
loop_
_audit_author_name
_audit_author_address
'Qi Sun'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-07-16 deposited with the CCDC.	2023-10-17 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT340_1_a                 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01267 Ang.  
RESPONSE: This is caused by the poor quality of the crystal.
;
# 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            'C6 H7 N9 O7'
_chemical_formula_weight         317.21

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   11.292(7)
_cell_length_b                   4.451(3)
_cell_length_c                   12.821(8)
_cell_angle_alpha                90
_cell_angle_beta                 112.416(12)
_cell_angle_gamma                90
_cell_volume                     595.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1343
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      20.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.160
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.992
_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            9101
_diffrn_reflns_av_unetI/netI     0.1335
_diffrn_reflns_av_R_equivalents  0.1417
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.050
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_point_group_measured_fraction_full 0.938
_reflns_number_total             1972
_reflns_number_gt                1117
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.654
_reflns_Friedel_fraction_max     0.865
_reflns_Friedel_fraction_full    0.865

_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)+(0.0874P)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 329 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.5(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1972
_refine_ls_number_parameters     205
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1498
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.1845
_refine_ls_wR_factor_gt          0.1510
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0902(7) 0.855(2) 0.7632(7) 0.037(2) Uani 1 1 d . . . . .
C2 C 1.0026(8) 0.960(2) 0.6566(7) 0.040(2) Uani 1 1 d . . . . .
C3 C 0.8668(8) 0.874(2) 0.5959(7) 0.039(2) Uani 1 1 d . . . . .
C4 C 0.6826(8) 0.861(2) 0.4751(7) 0.035(2) Uani 1 1 d . . . . .
C5 C 0.5633(8) 0.894(2) 0.3816(8) 0.041(2) Uani 1 1 d . . . . .
C6 C 0.4261(8) 1.077(2) 0.2302(7) 0.041(2) Uani 1 1 d . . . . .
N1 N 1.1486(7) 0.5786(19) 0.9249(7) 0.052(2) Uani 1 1 d . . . . .
N2 N 1.0599(6) 0.6449(18) 0.8271(6) 0.043(2) Uani 1 1 d . . . . .
N3 N 1.1998(7) 0.9987(19) 0.7825(6) 0.052(2) Uani 1 1 d . . . . .
N4 N 1.0530(7) 1.152(2) 0.6126(6) 0.054(2) Uani 1 1 d . . . . .
N5 N 0.7873(6) 1.0086(17) 0.5000(6) 0.040(2) Uani 1 1 d . . . . .
H5 H 0.8034 1.1570 0.4644 0.048 Uiso 1 1 calc R U . . .
N6 N 0.8171(7) 0.649(2) 0.6305(6) 0.055(2) Uani 1 1 d . . . . .
N7 N 0.4608(7) 0.7431(19) 0.3645(6) 0.048(2) Uani 1 1 d . . . . .
N8 N 0.3723(6) 0.8605(18) 0.2653(6) 0.043(2) Uani 1 1 d . . . . .
N9 N 0.3809(6) 1.2526(19) 0.1440(6) 0.049(2) Uani 1 1 d . . . . .
H9A H 0.3022 1.2364 0.0984 0.059 Uiso 1 1 calc R U . . .
H9B H 0.4294 1.3862 0.1322 0.059 Uiso 1 1 calc R U . . .
O1 O 1.1197(6) 0.3821(16) 0.9832(5) 0.056(2) Uani 1 1 d . . . . .
O2 O 1.2589(6) 0.6908(19) 0.9612(6) 0.078(3) Uani 1 1 d . . . . .
O3 O 1.1766(6) 1.1829(17) 0.6900(5) 0.062(2) Uani 1 1 d . . . . .
O4 O 0.6894(5) 0.6401(18) 0.5476(5) 0.0558(19) Uani 1 1 d . . . . .
O5 O 0.5504(5) 1.1089(13) 0.3015(5) 0.0398(16) Uani 1 1 d . . . . .
O6 O 0.8634(6) 0.2208(17) 0.8193(7) 0.059(2) Uani 1 1 d D . . . .
H6A H 0.889(11) 0.13(2) 0.881(5) 0.088 Uiso 1 1 d D U . . .
H6B H 0.863(11) 0.409(7) 0.827(10) 0.088 Uiso 1 1 d D U . . .
O7 O 0.5402(5) 0.6128(18) 0.0811(5) 0.068(2) Uani 1 1 d D . . . .
H7A H 0.5282 0.7928 0.0595 0.102 Uiso 1 1 d DR U . . .
H7B H 0.5985 0.6772 0.1384 0.102 Uiso 1 1 d DR 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 N3 1.330(11) . ?
C1 N2 1.369(10) . ?
C1 C2 1.426(12) . ?
C2 N4 1.272(11) . ?
C2 C3 1.482(11) . ?
C3 N6 1.304(12) . ?
C3 N5 1.355(10) . ?
C4 N5 1.281(10) . ?
C4 O4 1.337(10) . ?
C4 C5 1.429(11) . ?
C5 N7 1.282(11) . ?
C5 O5 1.370(11) . ?
C6 N9 1.290(11) . ?
C6 N8 1.306(11) . ?
C6 O5 1.360(9) . ?
N1 O2 1.255(9) . ?
N1 O1 1.271(9) . ?
N1 N2 1.306(9) . ?
N3 O3 1.382(9) . ?
N4 O3 1.377(9) . ?
N6 O4 1.429(9) . ?
N7 N8 1.386(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
N3 C1 N2 130.1(8) . . ?
N3 C1 C2 106.1(8) . . ?
N2 C1 C2 123.8(8) . . ?
N4 C2 C1 112.4(8) . . ?
N4 C2 C3 119.3(8) . . ?
C1 C2 C3 128.3(8) . . ?
N6 C3 N5 115.3(8) . . ?
N6 C3 C2 120.8(8) . . ?
N5 C3 C2 123.8(8) . . ?
N5 C4 O4 113.6(7) . . ?
N5 C4 C5 130.0(8) . . ?
O4 C4 C5 116.3(8) . . ?
N7 C5 O5 114.0(8) . . ?
N7 C5 C4 126.2(9) . . ?
O5 C5 C4 119.7(8) . . ?
N9 C6 N8 131.2(8) . . ?
N9 C6 O5 118.8(9) . . ?
N8 C6 O5 110.0(8) . . ?
O2 N1 O1 119.8(8) . . ?
O2 N1 N2 123.8(9) . . ?
O1 N1 N2 116.4(8) . . ?
N1 N2 C1 117.0(7) . . ?
C1 N3 O3 105.5(7) . . ?
C2 N4 O3 104.5(7) . . ?
C4 N5 C3 103.2(7) . . ?
C3 N6 O4 102.2(7) . . ?
C5 N7 N8 104.3(8) . . ?
C6 N8 N7 109.1(7) . . ?
N4 O3 N3 111.5(7) . . ?
C4 O4 N6 105.7(6) . . ?
C6 O5 C5 102.5(7) . . ?

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
N3 C1 C2 N4 0.3(11) . . . . ?
N2 C1 C2 N4 -179.2(8) . . . . ?
N3 C1 C2 C3 -179.5(8) . . . . ?
N2 C1 C2 C3 1.1(14) . . . . ?
N4 C2 C3 N6 170.5(9) . . . . ?
C1 C2 C3 N6 -9.8(14) . . . . ?
N4 C2 C3 N5 -6.7(13) . . . . ?
C1 C2 C3 N5 173.0(9) . . . . ?
N5 C4 C5 N7 -177.6(9) . . . . ?
O4 C4 C5 N7 4.3(14) . . . . ?
N5 C4 C5 O5 0.5(15) . . . . ?
O4 C4 C5 O5 -177.7(7) . . . . ?
O2 N1 N2 C1 -1.7(13) . . . . ?
O1 N1 N2 C1 -179.6(7) . . . . ?
N3 C1 N2 N1 3.1(13) . . . . ?
C2 C1 N2 N1 -177.6(8) . . . . ?
N2 C1 N3 O3 179.6(8) . . . . ?
C2 C1 N3 O3 0.2(9) . . . . ?
C1 C2 N4 O3 -0.6(10) . . . . ?
C3 C2 N4 O3 179.2(8) . . . . ?
O4 C4 N5 C3 -0.6(9) . . . . ?
C5 C4 N5 C3 -178.7(10) . . . . ?
N6 C3 N5 C4 0.8(10) . . . . ?
C2 C3 N5 C4 178.2(9) . . . . ?
N5 C3 N6 O4 -0.7(10) . . . . ?
C2 C3 N6 O4 -178.2(7) . . . . ?
O5 C5 N7 N8 0.7(10) . . . . ?
C4 C5 N7 N8 178.8(8) . . . . ?
N9 C6 N8 N7 -178.5(10) . . . . ?
O5 C6 N8 N7 1.0(10) . . . . ?
C5 N7 N8 C6 -1.0(10) . . . . ?
C2 N4 O3 N3 0.7(10) . . . . ?
C1 N3 O3 N4 -0.6(10) . . . . ?
N5 C4 O4 N6 0.2(9) . . . . ?
C5 C4 O4 N6 178.6(8) . . . . ?
C3 N6 O4 C4 0.3(9) . . . . ?
N9 C6 O5 C5 179.0(8) . . . . ?
N8 C6 O5 C5 -0.6(9) . . . . ?
N7 C5 O5 C6 -0.1(10) . . . . ?
C4 C5 O5 C6 -178.4(8) . . . . ?

_refine_diff_density_max         0.358
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.076



####################################################################### 
# 
# 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_sqsan13_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2281795'
loop_
_audit_author_name
_audit_author_address
'Qi Sun'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-07-16 deposited with the CCDC.	2023-10-17 downloaded from the CCDC.
;
_audit_creation_date             2021-04-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C6 H N11 O5), H2 O'
_chemical_formula_sum            'C12 H4 N22 O11'
_chemical_formula_weight         632.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'x, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'-x, y-1/2, z-1/2'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.604(2)
_cell_length_b                   40.625(8)
_cell_length_c                   5.931(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2314.1(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9812
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      55.078
_cell_measurement_theta_min      3.787
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.909
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1454 before and 0.0725 after correction. The Ratio of minimum to maximum transmission is 0.7852. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            20898
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.923
_diffrn_reflns_theta_min         1.892
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2144
_reflns_number_total             2190
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0585P)²+1.4567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1110
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 N9(H9), O6(H6)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.31776(14) 0.21360(3) 0.3675(2) 0.0358(3) Uani 1 1 d . . . . .
O2 O 0.11404(14) 0.11570(3) 0.9576(2) 0.0373(3) Uani 1 1 d . . . . .
O3 O -0.19611(12) 0.09517(3) 0.6449(2) 0.0277(3) Uani 1 1 d . . . . .
O4 O -0.43462(13) 0.02009(3) 0.7950(2) 0.0328(3) Uani 1 1 d . . . . .
O5 O -0.57599(13) 0.03442(3) 0.5293(2) 0.0362(3) Uani 1 1 d . . . . .
N1 N 0.61469(17) 0.22471(4) 1.0308(3) 0.0356(4) Uani 1 1 d . . . . .
N2 N 0.52922(15) 0.20947(3) 0.9553(2) 0.0286(3) Uani 1 1 d . . . . .
N3 N 0.43458(16) 0.18952(4) 0.9011(3) 0.0324(4) Uani 1 1 d . . . . .
N4 N 0.41040(16) 0.21733(4) 0.5451(2) 0.0315(4) Uani 1 1 d . . . . .
N5 N 0.22300(16) 0.18909(4) 0.4104(3) 0.0317(4) Uani 1 1 d . . . . .
N6 N 0.21789(16) 0.13876(4) 0.9072(3) 0.0364(4) Uani 1 1 d . . . . .
N7 N 0.04981(15) 0.13976(3) 0.6380(2) 0.0268(3) Uani 1 1 d . . . . .
N8 N -0.10354(15) 0.07148(3) 0.9480(2) 0.0291(3) Uani 1 1 d . . . . .
N9 N -0.22270(15) 0.05545(3) 0.8838(2) 0.0270(3) Uani 1 1 d . . . . .
H9 H -0.253693 0.038668 0.957052 0.032 Uiso 1 1 d R . . . .
N10 N -0.38768(15) 0.06445(3) 0.5719(2) 0.0293(3) Uani 1 1 d . . . . .
N11 N -0.46761(15) 0.03840(3) 0.6381(2) 0.0285(3) Uani 1 1 d . . . . .
C1 C 0.37316(17) 0.19541(4) 0.6923(3) 0.0264(4) Uani 1 1 d . . . . .
C2 C 0.25528(17) 0.17770(4) 0.6092(3) 0.0256(4) Uani 1 1 d . . . . .
C3 C 0.17447(17) 0.15187(4) 0.7188(3) 0.0262(4) Uani 1 1 d . . . . .
C4 C 0.02137(17) 0.11797(4) 0.7895(3) 0.0275(4) Uani 1 1 d . . . . .
C5 C -0.09210(17) 0.09449(4) 0.8015(3) 0.0272(4) Uani 1 1 d . . . . .
C6 C -0.27840(17) 0.06920(4) 0.7016(3) 0.0261(4) Uani 1 1 d . . . . .
O6 O 0.250000 0.000000 0.8476(3) 0.0359(4) Uani 1 2 d S T P . .
H6 H 0.182400 -0.006500 0.747660 0.054 Uiso 1 1 d R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N4 1.387(2) . ?
O1 N5 1.3727(18) . ?
O2 N6 1.4005(19) . ?
O2 C4 1.340(2) . ?
O3 C5 1.364(2) . ?
O3 C6 1.3604(19) . ?
O4 N11 1.2330(19) . ?
O5 N11 1.2354(19) . ?
N1 N2 1.121(2) . ?
N2 N3 1.259(2) . ?
N3 C1 1.392(2) . ?
N4 C1 1.298(2) . ?
N5 C2 1.304(2) . ?
N6 C3 1.306(2) . ?
N7 C3 1.380(2) . ?
N7 C4 1.291(2) . ?
N8 N9 1.371(2) . ?
N8 C5 1.281(2) . ?
N9 H9 0.8616 . ?
N9 C6 1.329(2) . ?
N10 N11 1.365(2) . ?
N10 C6 1.315(2) . ?
C1 C2 1.429(2) . ?
C2 C3 1.458(2) . ?
C4 C5 1.450(2) . ?
O6 H6 0.9179 . ?

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
N5 O1 N4 111.34(12) . . ?
C4 O2 N6 105.57(13) . . ?
C6 O3 C5 103.97(12) . . ?
N1 N2 N3 170.24(17) . . ?
N2 N3 C1 115.00(14) . . ?
C1 N4 O1 105.00(14) . . ?
C2 N5 O1 105.51(14) . . ?
C3 N6 O2 103.18(14) . . ?
C4 N7 C3 100.74(14) . . ?
C5 N8 N9 103.29(14) . . ?
N8 N9 H9 121.6 . . ?
C6 N9 N8 111.25(13) . . ?
C6 N9 H9 127.1 . . ?
C6 N10 N11 113.22(14) . . ?
O4 N11 O5 122.13(14) . . ?
O4 N11 N10 122.71(14) . . ?
O5 N11 N10 115.17(14) . . ?
N3 C1 C2 123.77(15) . . ?
N4 C1 N3 126.83(16) . . ?
N4 C1 C2 109.39(15) . . ?
N5 C2 C1 108.76(15) . . ?
N5 C2 C3 122.12(15) . . ?
C1 C2 C3 129.08(16) . . ?
N6 C3 N7 115.37(15) . . ?
N6 C3 C2 120.32(15) . . ?
N7 C3 C2 124.30(15) . . ?
O2 C4 C5 114.68(14) . . ?
N7 C4 O2 115.13(15) . . ?
N7 C4 C5 130.12(16) . . ?
O3 C5 C4 120.23(14) . . ?
N8 C5 O3 114.44(15) . . ?
N8 C5 C4 125.30(16) . . ?
N9 C6 O3 107.04(14) . . ?
N10 C6 O3 115.64(14) . . ?
N10 C6 N9 137.31(16) . . ?

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
O1 N4 C1 N3 -179.79(16) . . . . ?
O1 N4 C1 C2 -0.45(18) . . . . ?
O1 N5 C2 C1 -0.20(18) . . . . ?
O1 N5 C2 C3 177.71(14) . . . . ?
O2 N6 C3 N7 0.3(2) . . . . ?
O2 N6 C3 C2 179.69(14) . . . . ?
O2 C4 C5 O3 177.44(14) . . . . ?
O2 C4 C5 N8 -4.6(3) . . . . ?
N2 N3 C1 N4 5.5(3) . . . . ?
N2 N3 C1 C2 -173.70(15) . . . . ?
N3 C1 C2 N5 179.79(16) . . . . ?
N3 C1 C2 C3 2.1(3) . . . . ?
N4 O1 N5 C2 -0.08(18) . . . . ?
N4 C1 C2 N5 0.43(19) . . . . ?
N4 C1 C2 C3 -177.28(16) . . . . ?
N5 O1 N4 C1 0.35(18) . . . . ?
N5 C2 C3 N6 173.01(17) . . . . ?
N5 C2 C3 N7 -7.7(3) . . . . ?
N6 O2 C4 N7 -1.0(2) . . . . ?
N6 O2 C4 C5 176.43(14) . . . . ?
N7 C4 C5 O3 -5.6(3) . . . . ?
N7 C4 C5 N8 172.38(18) . . . . ?
N8 N9 C6 O3 -0.87(18) . . . . ?
N8 N9 C6 N10 -179.89(19) . . . . ?
N9 N8 C5 O3 0.59(19) . . . . ?
N9 N8 C5 C4 -177.52(16) . . . . ?
N11 N10 C6 O3 -179.12(13) . . . . ?
N11 N10 C6 N9 -0.2(3) . . . . ?
C1 C2 C3 N6 -9.5(3) . . . . ?
C1 C2 C3 N7 169.79(16) . . . . ?
C3 N7 C4 O2 1.09(19) . . . . ?
C3 N7 C4 C5 -175.83(17) . . . . ?
C4 O2 N6 C3 0.37(18) . . . . ?
C4 N7 C3 N6 -0.84(19) . . . . ?
C4 N7 C3 C2 179.79(16) . . . . ?
C5 O3 C6 N9 1.13(16) . . . . ?
C5 O3 C6 N10 -179.61(14) . . . . ?
C5 N8 N9 C6 0.19(18) . . . . ?
C6 O3 C5 N8 -1.11(19) . . . . ?
C6 O3 C5 C4 177.10(15) . . . . ?
C6 N10 N11 O4 -4.4(2) . . . . ?
C6 N10 N11 O5 175.58(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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 2281794'
loop_
_audit_author_name
_audit_author_address
'Qi Sun'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-07-16 deposited with the CCDC.	2023-10-17 downloaded from the CCDC.
;
_audit_creation_date             2021-09-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H2 N10 O7, 2(H2 O)'
_chemical_formula_sum            'C6 H6 N10 O9'
_chemical_formula_weight         362.21
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   23.945(3)
_cell_length_b                   4.5598(6)
_cell_length_c                   11.7638(17)
_cell_angle_alpha                90
_cell_angle_beta                 90.120(10)
_cell_angle_gamma                90
_cell_volume                     1284.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3283
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.730
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1531 before and 0.0551 after correction. The Ratio of minimum to maximum transmission is 0.8848. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.873
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13279
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.473
_diffrn_reflns_theta_min         1.927
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2033
_reflns_number_total             2648
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.0080(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         2648
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0622P)²+0.2071P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1291
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.593(2)
 0.407(2)
2. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
3.a Free rotating group:
 O8(H8A,H8B), O9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N9(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.94403(10) 1.1784(5) 0.0083(2) 0.0320(6) Uani 1 1 d . . . . .
O2 O 0.93190(11) 0.8057(6) -0.1038(2) 0.0335(7) Uani 1 1 d . . . . .
O3 O 0.82753(9) 0.8611(5) 0.2071(2) 0.0245(6) Uani 1 1 d . . . . .
O4 O 0.75260(10) 0.7383(5) 0.3722(2) 0.0295(6) Uani 1 1 d . . . . .
O5 O 0.67924(10) 1.2550(6) 0.7832(3) 0.0345(6) Uani 1 1 d . . . . .
O6 O 0.60273(14) 0.9976(7) 0.4702(3) 0.0528(9) Uani 1 1 d . . . . .
O7 O 0.55072(14) 0.6116(9) 0.4946(4) 0.0685(11) Uani 1 1 d . . . . .
N1 N 0.91984(12) 0.9478(6) -0.0191(3) 0.0258(7) Uani 1 1 d . . . . .
N2 N 0.87689(11) 0.8384(6) 0.0448(3) 0.0271(7) Uani 1 1 d . . . . .
N3 N 0.88800(11) 1.2110(6) 0.1962(3) 0.0235(7) Uani 1 1 d . . . . .
H3 H 0.914742 1.325804 0.170792 0.028 Uiso 1 1 calc R . . . .
N4 N 0.86102(11) 1.2473(6) 0.3002(3) 0.0247(7) Uani 1 1 d . . . . .
N5 N 0.77486(11) 1.1200(6) 0.4819(3) 0.0240(7) Uani 1 1 d . . . . .
N6 N 0.71513(11) 0.7352(7) 0.4643(3) 0.0309(7) Uani 1 1 d . . . . .
N7 N 0.71827(12) 1.2422(7) 0.6971(3) 0.0304(7) Uani 1 1 d . . . . .
N8 N 0.63597(13) 1.0638(7) 0.7639(3) 0.0313(8) Uani 1 1 d . . . . .
N9 N 0.61399(13) 0.7144(7) 0.6252(3) 0.0320(8) Uani 1 1 d . . . . .
H9 H 0.609705 0.544511 0.659604 0.038 Uiso 1 1 calc R . . . .
N10 N 0.58707(14) 0.7798(9) 0.5236(4) 0.0454(9) Uani 1 1 d . . . . .
C1 C 0.64808(14) 0.9334(8) 0.6693(3) 0.0257(8) Uani 1 1 d . . . . .
C2 C 0.70012(14) 1.0420(7) 0.6262(3) 0.0247(8) Uani 1 1 d . . . . .
C3 C 0.73052(14) 0.9636(7) 0.5234(3) 0.0242(8) Uani 1 1 d . . . . .
C4 C 0.78583(14) 0.9710(7) 0.3904(3) 0.0228(8) Uani 1 1 d . . . . .
C5 C 0.82648(14) 1.0376(7) 0.3016(3) 0.0222(7) Uani 1 1 d . . . . .
C6 C 0.86794(13) 0.9794(7) 0.1405(3) 0.0221(7) Uani 1 1 d . . . . .
O8 O 0.53105(12) 1.0044(6) 0.2688(3) 0.0390(7) Uani 1 1 d . . . . .
H8A H 0.503565 0.885179 0.259620 0.058 Uiso 1 1 d G . . . .
H8B H 0.543558 0.989540 0.337054 0.058 Uiso 1 1 d G . . . .
O9 O 1.01803(10) 0.4067(6) -0.1822(2) 0.0291(6) Uani 1 1 d . . . . .
H9A H 0.987705 0.391052 -0.142066 0.044 Uiso 1 1 d G . . . .
H9B H 1.013676 0.281121 -0.237178 0.044 Uiso 1 1 d G . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.243(4) . ?
O2 N1 1.224(4) . ?
O3 C5 1.372(4) . ?
O3 C6 1.358(4) . ?
O4 N6 1.408(4) . ?
O4 C4 1.343(4) . ?
O5 N7 1.381(4) . ?
O5 N8 1.373(4) . ?
O6 N10 1.234(5) . ?
O7 N10 1.208(5) . ?
N1 N2 1.369(4) . ?
N2 C6 1.314(5) . ?
N3 H3 0.8800 . ?
N3 N4 1.394(4) . ?
N3 C6 1.332(4) . ?
N4 C5 1.265(4) . ?
N5 C3 1.370(4) . ?
N5 C4 1.300(5) . ?
N6 C3 1.305(5) . ?
N7 C2 1.310(5) . ?
N8 C1 1.295(5) . ?
N9 H9 0.8800 . ?
N9 N10 1.390(5) . ?
N9 C1 1.389(5) . ?
C1 C2 1.434(5) . ?
C2 C3 1.457(5) . ?
C4 C5 1.461(5) . ?
O8 H8A 0.8601 . ?
O8 H8B 0.8594 . ?
O9 H9A 0.8700 . ?
O9 H9B 0.8698 . ?

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
C6 O3 C5 104.4(3) . . ?
C4 O4 N6 105.3(3) . . ?
N8 O5 N7 111.3(3) . . ?
O1 N1 N2 121.0(3) . . ?
O2 N1 O1 123.3(3) . . ?
O2 N1 N2 115.7(3) . . ?
C6 N2 N1 114.6(3) . . ?
N4 N3 H3 124.5 . . ?
C6 N3 H3 124.5 . . ?
C6 N3 N4 111.0(3) . . ?
C5 N4 N3 103.1(3) . . ?
C4 N5 C3 100.4(3) . . ?
C3 N6 O4 102.8(3) . . ?
C2 N7 O5 105.8(3) . . ?
C1 N8 O5 105.3(3) . . ?
N10 N9 H9 122.0 . . ?
C1 N9 H9 122.0 . . ?
C1 N9 N10 116.0(3) . . ?
O6 N10 N9 118.0(3) . . ?
O7 N10 O6 126.0(4) . . ?
O7 N10 N9 116.0(4) . . ?
N8 C1 N9 121.2(3) . . ?
N8 C1 C2 109.9(3) . . ?
N9 C1 C2 128.8(3) . . ?
N7 C2 C1 107.6(3) . . ?
N7 C2 C3 122.3(3) . . ?
C1 C2 C3 130.1(3) . . ?
N5 C3 C2 123.8(3) . . ?
N6 C3 N5 116.4(3) . . ?
N6 C3 C2 119.8(3) . . ?
O4 C4 C5 116.5(3) . . ?
N5 C4 O4 115.1(3) . . ?
N5 C4 C5 128.3(3) . . ?
O3 C5 C4 118.1(3) . . ?
N4 C5 O3 114.8(3) . . ?
N4 C5 C4 127.1(3) . . ?
N2 C6 O3 114.7(3) . . ?
N2 C6 N3 138.6(3) . . ?
N3 C6 O3 106.7(3) . . ?
H8A O8 H8B 109.4 . . ?
H9A O9 H9B 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
O1 N1 N2 C6 -6.4(5) . . . . ?
O2 N1 N2 C6 174.2(3) . . . . ?
O4 N6 C3 N5 -0.7(4) . . . . ?
O4 N6 C3 C2 178.2(3) . . . . ?
O4 C4 C5 O3 0.4(5) . . . . ?
O4 C4 C5 N4 178.8(3) . . . . ?
O5 N7 C2 C1 1.0(4) . . . . ?
O5 N7 C2 C3 -179.7(3) . . . . ?
O5 N8 C1 N9 177.6(3) . . . . ?
O5 N8 C1 C2 -0.1(4) . . . . ?
N1 N2 C6 O3 -176.3(3) . . . . ?
N1 N2 C6 N3 1.9(6) . . . . ?
N3 N4 C5 O3 -0.1(4) . . . . ?
N3 N4 C5 C4 -178.6(3) . . . . ?
N4 N3 C6 O3 0.0(4) . . . . ?
N4 N3 C6 N2 -178.3(4) . . . . ?
N5 C4 C5 O3 -174.4(3) . . . . ?
N5 C4 C5 N4 4.0(6) . . . . ?
N6 O4 C4 N5 -0.2(4) . . . . ?
N6 O4 C4 C5 -175.7(3) . . . . ?
N7 O5 N8 C1 0.7(4) . . . . ?
N7 C2 C3 N5 -11.1(5) . . . . ?
N7 C2 C3 N6 170.1(4) . . . . ?
N8 O5 N7 C2 -1.1(4) . . . . ?
N8 C1 C2 N7 -0.6(4) . . . . ?
N8 C1 C2 C3 -179.8(4) . . . . ?
N9 C1 C2 N7 -178.1(4) . . . . ?
N9 C1 C2 C3 2.8(7) . . . . ?
N10 N9 C1 N8 113.8(4) . . . . ?
N10 N9 C1 C2 -69.1(5) . . . . ?
C1 N9 N10 O6 13.0(5) . . . . ?
C1 N9 N10 O7 -168.4(4) . . . . ?
C1 C2 C3 N5 168.0(3) . . . . ?
C1 C2 C3 N6 -10.8(6) . . . . ?
C3 N5 C4 O4 -0.2(4) . . . . ?
C3 N5 C4 C5 174.7(4) . . . . ?
C4 O4 N6 C3 0.5(4) . . . . ?
C4 N5 C3 N6 0.6(4) . . . . ?
C4 N5 C3 C2 -178.3(4) . . . . ?
C5 O3 C6 N2 178.6(3) . . . . ?
C5 O3 C6 N3 -0.1(3) . . . . ?
C6 O3 C5 N4 0.2(4) . . . . ?
C6 O3 C5 C4 178.8(3) . . . . ?
C6 N3 N4 C5 0.1(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.593(2)
2 0.407(2)

