# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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 1889333'
loop_
_audit_author_name
_audit_author_address
'jie Tang' 'Nanjing University of Science and Technology'
_audit_update_record             
;
2019-06-19 deposited with the CCDC.	2019-06-26 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         'C9 H6 N8 O4'
_chemical_formula_sum            'C9 H6 N8 O4'
_chemical_formula_weight         290.22

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   7.5895(8)
_cell_length_b                   9.8629(10)
_cell_length_c                   14.7226(17)
_cell_angle_alpha                90
_cell_angle_beta                 95.149(4)
_cell_angle_gamma                90
_cell_volume                     1097.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1007
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      24.53

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.144
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6411
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5162
_diffrn_reflns_av_unetI/netI     0.1007
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.396
_diffrn_reflns_theta_max         25.409
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             1989
_reflns_number_gt                1128
_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)+(0.0365P)²+0.5939P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1989
_refine_ls_number_parameters     196
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1335
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1241
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3184(5) -0.0917(3) -0.0745(3) 0.0313(9) Uani 1 1 d . . . . .
H1 H 0.3600 -0.1498 -0.1194 0.038 Uiso 1 1 calc R U . . .
C2 C 0.3154(4) 0.0526(3) -0.0802(3) 0.0244(8) Uani 1 1 d . . . . .
C3 C 0.2455(4) 0.0966(3) -0.0005(2) 0.0244(9) Uani 1 1 d . . . . .
C4 C 0.2225(4) 0.2322(3) 0.0215(2) 0.0288(9) Uani 1 1 d . . . . .
H4 H 0.1747 0.2597 0.0760 0.035 Uiso 1 1 calc R U . . .
C5 C 0.2741(5) 0.3230(3) -0.0413(3) 0.0302(9) Uani 1 1 d . . . . .
C6 C 0.3389(5) 0.2882(3) -0.1238(3) 0.0301(9) Uani 1 1 d . . . . .
H6 H 0.3691 0.3560 -0.1656 0.036 Uiso 1 1 calc R U . . .
C7 C 0.3579(4) 0.1534(3) -0.1427(2) 0.0252(8) Uani 1 1 d . . . . .
C8 C 0.1372(4) -0.0289(3) 0.1307(2) 0.0265(9) Uani 1 1 d . . . . .
C9 C 0.0519(5) -0.1065(3) 0.2549(3) 0.0338(10) Uani 1 1 d . . . . .
H9 H 0.0292 -0.1657 0.3034 0.041 Uiso 1 1 calc R U . . .
N1 N 0.2112(4) -0.0192(3) 0.0475(2) 0.0267(7) Uani 1 1 d . . . . .
N2 N 0.2557(4) -0.1340(3) 0.0014(2) 0.0310(8) Uani 1 1 d . . . . .
N3 N 0.0105(4) 0.0222(3) 0.2510(2) 0.0369(8) Uani 1 1 d . . . . .
N4 N 0.0650(4) 0.0733(3) 0.1700(2) 0.0323(8) Uani 1 1 d . . . . .
N5 N 0.1320(4) -0.1438(3) 0.1798(2) 0.0294(8) Uani 1 1 d . . . . .
N6 N 0.2183(4) -0.2694(3) 0.1684(2) 0.0382(9) Uani 1 1 d D . . . .
H6A H 0.215(5) -0.284(4) 0.1068(19) 0.046 Uiso 1 1 d D U . . .
H6B H 0.145(4) -0.334(3) 0.188(3) 0.046 Uiso 1 1 d D U . . .
N7 N 0.2611(4) 0.4678(3) -0.0185(2) 0.0406(9) Uani 1 1 d . . . . .
N8 N 0.4285(4) 0.1146(3) -0.2279(2) 0.0321(8) Uani 1 1 d . . . . .
O2 O 0.1855(4) 0.4977(3) 0.0481(2) 0.0671(11) Uani 1 1 d . . . . .
O3 O 0.3271(4) 0.5501(2) -0.0675(2) 0.0557(9) Uani 1 1 d . . . . .
O4 O 0.4167(4) 0.1956(3) -0.2907(2) 0.0471(8) Uani 1 1 d . . . . .
O5 O 0.4959(4) 0.0015(2) -0.23020(18) 0.0433(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 N2 1.321(4) . ?
C1 C2 1.425(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.400(5) . ?
C2 C7 1.412(5) . ?
C3 N1 1.380(4) . ?
C3 C4 1.391(4) . ?
C4 C5 1.369(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(5) . ?
C5 N7 1.472(4) . ?
C6 C7 1.368(4) . ?
C6 H6 0.9500 . ?
C7 N8 1.459(4) . ?
C8 N4 1.307(4) . ?
C8 N5 1.347(4) . ?
C8 N1 1.397(4) . ?
C9 N3 1.309(4) . ?
C9 N5 1.359(4) . ?
C9 H9 0.9500 . ?
N1 N2 1.377(4) . ?
N3 N4 1.391(4) . ?
N5 N6 1.418(4) . ?
N6 H6A 0.92(3) . ?
N6 H6B 0.91(3) . ?
N7 O2 1.215(4) . ?
N7 O3 1.223(4) . ?
N8 O4 1.219(4) . ?
N8 O5 1.229(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C2 111.1(3) . . ?
N2 C1 H1 124.5 . . ?
C2 C1 H1 124.5 . . ?
C3 C2 C7 117.0(3) . . ?
C3 C2 C1 105.4(3) . . ?
C7 C2 C1 137.6(3) . . ?
N1 C3 C4 130.0(3) . . ?
N1 C3 C2 106.0(3) . . ?
C4 C3 C2 124.0(3) . . ?
C5 C4 C3 115.0(3) . . ?
C5 C4 H4 122.5 . . ?
C3 C4 H4 122.5 . . ?
C4 C5 C6 124.9(3) . . ?
C4 C5 N7 116.9(3) . . ?
C6 C5 N7 118.3(3) . . ?
C7 C6 C5 118.0(3) . . ?
C7 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C6 C7 C2 121.2(3) . . ?
C6 C7 N8 118.9(3) . . ?
C2 C7 N8 119.9(3) . . ?
N4 C8 N5 112.2(3) . . ?
N4 C8 N1 123.6(3) . . ?
N5 C8 N1 124.2(3) . . ?
N3 C9 N5 110.5(3) . . ?
N3 C9 H9 124.7 . . ?
N5 C9 H9 124.7 . . ?
N2 N1 C3 111.2(3) . . ?
N2 N1 C8 120.8(3) . . ?
C3 N1 C8 127.9(3) . . ?
C1 N2 N1 106.3(3) . . ?
C9 N3 N4 107.5(3) . . ?
C8 N4 N3 105.6(3) . . ?
C8 N5 C9 104.2(3) . . ?
C8 N5 N6 129.5(3) . . ?
C9 N5 N6 125.3(3) . . ?
N5 N6 H6A 107(2) . . ?
N5 N6 H6B 106(2) . . ?
H6A N6 H6B 103(3) . . ?
O2 N7 O3 124.3(3) . . ?
O2 N7 C5 117.7(3) . . ?
O3 N7 C5 118.0(3) . . ?
O4 N8 O5 125.2(3) . . ?
O4 N8 C7 118.2(3) . . ?
O5 N8 C7 116.6(3) . . ?

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_mo_20181093-TJ-SXSZCT_0m
_database_code_depnum_ccdc_archive 'CCDC 1900218'
loop_
_audit_author_name
_audit_author_address
'jie tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2019-02-28 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H23 Cl N16 O15'
_chemical_formula_weight         714.95

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'
Cl Cl 0.1484 0.1585 '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                   7.0409(14)
_cell_length_b                   10.232(2)
_cell_length_c                   19.848(4)
_cell_angle_alpha                87.614(5)
_cell_angle_beta                 85.009(5)
_cell_angle_gamma                82.298(5)
_cell_volume                     1411.0(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    727
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      19.26

_exptl_crystal_description       layered
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.238
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(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            11833
_diffrn_reflns_av_unetI/netI     0.1246
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.030
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             5683
_reflns_number_gt                2961
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.1296P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5683
_refine_ls_number_parameters     455
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1482
_refine_ls_R_factor_gt           0.0823
_refine_ls_wR_factor_ref         0.2536
_refine_ls_wR_factor_gt          0.2000
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_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
Cl1 Cl 0.49733(16) 0.79310(10) 0.60380(5) 0.0241(3) Uani 1 1 d . . . . .
O11 O 0.3659(6) 0.9493(4) 0.6895(2) 0.0486(11) Uani 1 1 d G . . . .
H11A H 0.274389 0.961129 0.721842 0.073 Uiso 1 1 d G U . . .
H11B H 0.432799 1.015190 0.687396 0.073 Uiso 1 1 d G U . . .
O6 O 0.2158(6) 0.9207(4) 0.5609(2) 0.0444(10) Uani 1 1 d G . . . .
H6A H 0.122349 0.974414 0.580084 0.067 Uiso 1 1 d G U . . .
H6B H 0.201618 0.844021 0.579839 0.067 Uiso 1 1 d G U . . .
O2 O 0.6475(7) 0.3845(4) 0.4334(2) 0.0542(11) Uani 1 1 d G . . . .
H2A H 0.739565 0.409464 0.454236 0.081 Uiso 1 1 d G U . . .
H2B H 0.575492 0.349521 0.465137 0.081 Uiso 1 1 d G U . . .
O7 O 0.0518(7) 0.7598(4) 0.7025(2) 0.0583(12) Uani 1 1 d . . . . .
O5 O 0.3965(6) 0.1502(4) 0.50979(19) 0.0468(10) Uani 1 1 d G . . . .
H5A H 0.419368 0.184185 0.547268 0.070 Uiso 1 1 d G U . . .
H5B H 0.317274 0.092241 0.518777 0.070 Uiso 1 1 d G U . . .
O4 O 0.7894(6) 0.6418(4) 0.5819(2) 0.0549(12) Uani 1 1 d G . . . .
H4A H 0.823981 0.557810 0.588878 0.082 Uiso 1 1 d G U . . .
H4B H 0.847204 0.667578 0.544131 0.082 Uiso 1 1 d G U . . .
O1 O 0.4972(7) 0.3283(4) 0.2928(2) 0.0548(12) Uani 1 1 d G . . . .
H1A H 0.464380 0.304945 0.254258 0.082 Uiso 1 1 d G U . . .
H1B H 0.477868 0.413894 0.294876 0.082 Uiso 1 1 d G U . . .
N4 N 0.0409(7) 0.1482(4) 0.7430(2) 0.0382(11) Uani 1 1 d . . . . .
H4 H 0.031436 0.069067 0.728927 0.046 Uiso 1 1 calc R U . . .
N3 N 0.0189(6) 0.2629(4) 0.7062(2) 0.0341(10) Uani 1 1 d . . . . .
O3 O 0.7542(6) 0.9143(4) 0.6265(2) 0.0570(12) Uani 1 1 d G . . . .
H3A H 0.808578 0.864208 0.657734 0.086 Uiso 1 1 d G U . . .
H3B H 0.770991 0.995825 0.631817 0.086 Uiso 1 1 d G U . . .
N12 N 0.5039(7) 0.1965(4) 0.6979(2) 0.0399(11) Uani 1 1 d . . . . .
N11 N 0.4703(7) 0.2496(4) 0.6363(2) 0.0408(11) Uani 1 1 d . . . . .
N13 N 0.5834(6) 0.2886(4) 0.7999(2) 0.0370(11) Uani 1 1 d . . . . .
N7 N -0.0842(7) 0.3231(5) 0.5400(2) 0.0440(12) Uani 1 1 d . . . . .
O15 O 0.6721(8) -0.2170(4) 0.8123(2) 0.0693(14) Uani 1 1 d . . . . .
N14 N 0.5974(7) 0.4013(5) 0.8329(2) 0.0442(12) Uani 1 1 d . . . . .
N6 N -0.0826(7) 0.1962(4) 0.5457(2) 0.0435(12) Uani 1 1 d . . . . .
H6 H -0.103212 0.146129 0.512763 0.052 Uiso 1 1 calc R U . . .
N10 N 0.4819(7) 0.3730(5) 0.6361(2) 0.0454(12) Uani 1 1 d . . . . .
H10 H 0.462555 0.427409 0.601118 0.054 Uiso 1 1 calc R U . . .
O8 O 0.1098(8) 0.7935(4) 0.8053(2) 0.0681(14) Uani 1 1 d . . . . .
N8 N -0.0436(7) 0.3691(4) 0.5994(2) 0.0428(12) Uani 1 1 d . . . . .
N2 N 0.1605(7) 0.3527(5) 0.9249(2) 0.0471(12) Uani 1 1 d . . . . .
N1 N 0.0809(7) 0.7202(5) 0.7609(2) 0.0483(12) Uani 1 1 d . . . . .
N5 N -0.0454(7) 0.1516(4) 0.6083(2) 0.0417(11) Uani 1 1 d . . . . .
O10 O 0.1622(8) 0.2330(5) 0.9362(2) 0.0730(15) Uani 1 1 d . . . . .
N9 N 0.5282(7) 0.4089(5) 0.6970(2) 0.0453(12) Uani 1 1 d . . . . .
O9 O 0.1920(8) 0.4293(5) 0.9664(2) 0.0740(15) Uani 1 1 d . . . . .
C16 C 0.5400(7) 0.2967(5) 0.7326(3) 0.0336(12) Uani 1 1 d . . . . .
C5 C 0.0860(7) 0.3153(5) 0.8080(2) 0.0310(11) Uani 1 1 d . . . . .
C4 C 0.0484(7) 0.3684(5) 0.7434(2) 0.0326(12) Uani 1 1 d . . . . .
C13 C 0.6199(8) 0.1786(5) 0.8411(3) 0.0345(12) Uani 1 1 d . . . . .
N16 N 0.6690(9) -0.1818(5) 0.8703(3) 0.0579(15) Uani 1 1 d . . . . .
O13 O 0.7854(10) 0.0838(6) 1.0646(2) 0.096(2) Uani 1 1 d . . . . .
C6 C 0.1175(8) 0.4032(5) 0.8569(3) 0.0358(12) Uani 1 1 d . . . . .
C3 C 0.0447(7) 0.5007(5) 0.7256(3) 0.0359(12) Uani 1 1 d . . . . .
H3 H 0.020383 0.535002 0.681481 0.043 Uiso 1 1 calc R U . . .
C12 C 0.6587(8) 0.2262(6) 0.9036(3) 0.0385(13) Uani 1 1 d . . . . .
C14 C 0.6249(8) 0.0466(5) 0.8278(3) 0.0384(13) Uani 1 1 d . . . . .
H14 H 0.601388 0.017334 0.784854 0.046 Uiso 1 1 calc R U . . .
C2 C 0.0792(8) 0.5789(5) 0.7769(3) 0.0372(12) Uani 1 1 d . . . . .
C8 C -0.0238(7) 0.2611(5) 0.6386(2) 0.0345(12) Uani 1 1 d . . . . .
N15 N 0.7560(9) 0.1697(6) 1.0207(3) 0.0640(16) Uani 1 1 d . . . . .
C7 C 0.0792(8) 0.1777(5) 0.8042(3) 0.0400(13) Uani 1 1 d . . . . .
H7 H 0.099375 0.115439 0.840545 0.048 Uiso 1 1 calc R U . . .
O12 O 0.7624(10) 0.2858(5) 1.0272(3) 0.0938(19) Uani 1 1 d . . . . .
O14 O 0.6697(11) -0.2560(5) 0.9190(3) 0.108(2) Uani 1 1 d . . . . .
C15 C 0.6423(8) 0.3625(6) 0.8949(3) 0.0438(14) Uani 1 1 d . . . . .
H15 H 0.660909 0.420790 0.929058 0.053 Uiso 1 1 calc R U . . .
C1 C 0.1165(8) 0.5346(6) 0.8424(3) 0.0425(14) Uani 1 1 d . . . . .
H1 H 0.140156 0.593489 0.875484 0.051 Uiso 1 1 calc R U . . .
C10 C 0.7083(9) -0.0023(6) 0.9443(3) 0.0488(15) Uani 1 1 d . . . . .
H10A H 0.737748 -0.066059 0.979300 0.059 Uiso 1 1 calc R U . . .
C11 C 0.7057(9) 0.1303(6) 0.9544(3) 0.0449(14) Uani 1 1 d . . . . .
C9 C 0.6669(9) -0.0398(6) 0.8816(3) 0.0461(15) 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
O11 H11A 0.8696 . ?
O11 H11B 0.8703 . ?
O6 H6A 0.8699 . ?
O6 H6B 0.8701 . ?
O2 H2A 0.8701 . ?
O2 H2B 0.8700 . ?
O7 N1 1.237(6) . ?
O5 H5A 0.8704 . ?
O5 H5B 0.8701 . ?
O4 H4A 0.8700 . ?
O4 H4B 0.8699 . ?
O1 H1A 0.8702 . ?
O1 H1B 0.8700 . ?
N4 C7 1.321(7) . ?
N4 N3 1.355(6) . ?
N4 H4 0.8800 . ?
N3 C4 1.381(6) . ?
N3 C8 1.401(6) . ?
O3 H3A 0.8699 . ?
O3 H3B 0.8700 . ?
N12 C16 1.322(6) . ?
N12 N11 1.343(6) . ?
N11 N10 1.276(6) . ?
N13 N14 1.370(6) . ?
N13 C13 1.373(6) . ?
N13 C16 1.393(7) . ?
N7 N6 1.297(6) . ?
N7 N8 1.353(6) . ?
O15 N16 1.217(6) . ?
N14 C15 1.328(7) . ?
N6 N5 1.341(6) . ?
N6 H6 0.8800 . ?
N10 N9 1.357(6) . ?
N10 H10 0.8800 . ?
O8 N1 1.227(6) . ?
N8 C8 1.324(7) . ?
N2 O9 1.214(6) . ?
N2 O10 1.234(6) . ?
N2 C6 1.467(7) . ?
N1 C2 1.469(7) . ?
N5 C8 1.327(7) . ?
N9 C16 1.320(7) . ?
C5 C6 1.402(7) . ?
C5 C4 1.405(7) . ?
C5 C7 1.421(7) . ?
C4 C3 1.382(7) . ?
C13 C14 1.383(7) . ?
C13 C12 1.412(7) . ?
N16 O14 1.205(7) . ?
N16 C9 1.477(8) . ?
O13 N15 1.223(7) . ?
C6 C1 1.363(8) . ?
C3 C2 1.379(7) . ?
C3 H3 0.9500 . ?
C12 C15 1.389(8) . ?
C12 C11 1.407(8) . ?
C14 C9 1.384(7) . ?
C14 H14 0.9500 . ?
C2 C1 1.393(8) . ?
N15 O12 1.208(7) . ?
N15 C11 1.477(7) . ?
C7 H7 0.9500 . ?
C15 H15 0.9500 . ?
C1 H1 0.9500 . ?
C10 C11 1.377(8) . ?
C10 C9 1.383(8) . ?
C10 H10A 0.9500 . ?

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
H11A O11 H11B 109.5 . . ?
H6A O6 H6B 104.5 . . ?
H2A O2 H2B 104.5 . . ?
H5A O5 H5B 109.4 . . ?
H4A O4 H4B 109.5 . . ?
H1A O1 H1B 109.4 . . ?
C7 N4 N3 107.0(4) . . ?
C7 N4 H4 126.5 . . ?
N3 N4 H4 126.5 . . ?
N4 N3 C4 111.5(4) . . ?
N4 N3 C8 119.4(4) . . ?
C4 N3 C8 129.1(4) . . ?
H3A O3 H3B 109.5 . . ?
C16 N12 N11 104.2(4) . . ?
N10 N11 N12 109.3(4) . . ?
N14 N13 C13 111.2(4) . . ?
N14 N13 C16 119.8(4) . . ?
C13 N13 C16 129.0(4) . . ?
N6 N7 N8 109.4(4) . . ?
C15 N14 N13 105.9(5) . . ?
N7 N6 N5 111.0(4) . . ?
N7 N6 H6 124.5 . . ?
N5 N6 H6 124.5 . . ?
N11 N10 N9 110.9(4) . . ?
N11 N10 H10 124.6 . . ?
N9 N10 H10 124.6 . . ?
C8 N8 N7 102.8(4) . . ?
O9 N2 O10 123.9(5) . . ?
O9 N2 C6 119.0(5) . . ?
O10 N2 C6 117.0(5) . . ?
O8 N1 O7 122.9(5) . . ?
O8 N1 C2 119.5(5) . . ?
O7 N1 C2 117.6(5) . . ?
C8 N5 N6 102.4(4) . . ?
C16 N9 N10 102.7(4) . . ?
N9 C16 N12 112.9(5) . . ?
N9 C16 N13 122.1(5) . . ?
N12 C16 N13 124.9(5) . . ?
C6 C5 C4 117.3(5) . . ?
C6 C5 C7 137.3(5) . . ?
C4 C5 C7 105.3(4) . . ?
N3 C4 C3 130.8(5) . . ?
N3 C4 C5 105.5(4) . . ?
C3 C4 C5 123.7(5) . . ?
N13 C13 C14 130.1(5) . . ?
N13 C13 C12 105.5(5) . . ?
C14 C13 C12 124.4(5) . . ?
O14 N16 O15 123.9(6) . . ?
O14 N16 C9 117.9(5) . . ?
O15 N16 C9 118.1(5) . . ?
C1 C6 C5 121.7(5) . . ?
C1 C6 N2 118.7(5) . . ?
C5 C6 N2 119.6(5) . . ?
C2 C3 C4 114.6(5) . . ?
C2 C3 H3 122.7 . . ?
C4 C3 H3 122.7 . . ?
C15 C12 C11 138.1(5) . . ?
C15 C12 C13 105.7(5) . . ?
C11 C12 C13 116.2(5) . . ?
C13 C14 C9 115.0(5) . . ?
C13 C14 H14 122.5 . . ?
C9 C14 H14 122.5 . . ?
C3 C2 C1 125.4(5) . . ?
C3 C2 N1 117.3(5) . . ?
C1 C2 N1 117.2(5) . . ?
N8 C8 N5 114.4(5) . . ?
N8 C8 N3 122.5(5) . . ?
N5 C8 N3 123.1(5) . . ?
O12 N15 O13 125.1(6) . . ?
O12 N15 C11 116.7(6) . . ?
O13 N15 C11 118.2(6) . . ?
N4 C7 C5 110.7(5) . . ?
N4 C7 H7 124.7 . . ?
C5 C7 H7 124.7 . . ?
N14 C15 C12 111.6(5) . . ?
N14 C15 H15 124.2 . . ?
C12 C15 H15 124.2 . . ?
C6 C1 C2 117.2(5) . . ?
C6 C1 H1 121.4 . . ?
C2 C1 H1 121.4 . . ?
C11 C10 C9 118.0(5) . . ?
C11 C10 H10A 121.0 . . ?
C9 C10 H10A 121.0 . . ?
C10 C11 C12 121.8(5) . . ?
C10 C11 N15 117.9(5) . . ?
C12 C11 N15 120.4(5) . . ?
C10 C9 C14 124.6(6) . . ?
C10 C9 N16 118.4(5) . . ?
C14 C9 N16 117.0(5) . . ?

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
O11 H11B N12 0.87 2.01 2.845(6) 160.7 1_565 yes
O5 H5A N11 0.87 1.99 2.862(6) 175.9 . yes
O4 H4A N8 0.87 2.04 2.898(6) 169.1 1_655 yes
O1 H1A O15 0.87 2.01 2.841(6) 159.8 2_656 yes
O1 H1B N9 0.87 1.82 2.685(6) 171.9 2_666 yes

_refine_diff_density_max         0.825
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.146

####################################################################### 
# 
# 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_mo_20181195-tj-sxszc_0m
_database_code_depnum_ccdc_archive 'CCDC 1900215'
loop_
_audit_author_name
_audit_author_address
'jie tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2019-02-28 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;
_audit_creation_date             2018-12-17
_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         'Cl, C9 H8 N9 O6'
_chemical_formula_sum            'C9 H8 Cl N9 O6'
_chemical_formula_weight         373.69
_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'
Cl Cl 0.1484 0.1585 '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      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                   7.773(6)
_cell_length_b                   9.309(8)
_cell_length_c                   10.386(8)
_cell_angle_alpha                77.691(17)
_cell_angle_beta                 78.764(17)
_cell_angle_gamma                87.961(18)
_cell_volume                     720.2(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1159
_cell_measurement_temperature    153
_cell_measurement_theta_max      25.526
_cell_measurement_theta_min      2.671
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.322
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0773 before and 0.0527 after correction. The Ratio of minimum to maximum transmission is 0.8320. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.16
_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  0.0468
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5635
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.422
_diffrn_reflns_theta_min         2.045
_diffrn_ambient_temperature      153.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.971
_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                2142
_reflns_number_total             2873
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.695
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2873
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0601
_refine_ls_restrained_S_all      1.025
_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)+(0.1204P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1697
_refine_ls_wR_factor_ref         0.1929
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2.a Rotating group:
 N9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N6(H6), N5(H5), C3(H3), C7(H7), C1(H1), C9(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
Cl1 Cl -0.00058(11) 0.39023(10) 0.80749(8) 0.0235(3) Uani 1 1 d . . . . .
O1 O 0.3563(3) 0.4248(3) 0.9652(2) 0.0252(6) Uani 1 1 d . . . . .
O2 O 0.5217(3) 0.2309(3) 0.9734(2) 0.0264(6) Uani 1 1 d . . . . .
O6 O 0.6777(3) 0.8390(3) 0.6623(3) 0.0282(6) Uani 1 1 d . . . . .
O5 O 0.8002(3) 0.8154(3) 0.4606(2) 0.0290(6) Uani 1 1 d . . . . .
O3 O 0.6554(3) 0.1933(3) 0.4472(3) 0.0307(6) Uani 1 1 d . . . . .
O4 O 0.9145(3) 0.2913(3) 0.4027(3) 0.0290(6) Uani 1 1 d . . . . .
N3 N 0.4697(4) 0.3472(3) 0.9144(3) 0.0185(6) Uani 1 1 d . . . . .
N6 N 0.0348(3) 0.0567(3) 0.8289(3) 0.0194(6) Uani 1 1 d . . . . .
H6 H 0.051168 0.152559 0.810535 0.023 Uiso 1 1 calc R . . . .
N8 N 0.0880(3) -0.1754(3) 0.8602(3) 0.0178(6) Uani 1 1 d . . . . .
N2 N 0.7635(4) 0.2760(3) 0.4646(3) 0.0191(6) Uani 1 1 d . . . . .
N9 N 0.1841(4) -0.3065(3) 0.8741(3) 0.0215(7) Uani 1 1 d . . . . .
H9A H 0.165783 -0.351685 0.959438 0.026 Uiso 1 1 d GR . . . .
H9B H 0.150223 -0.364461 0.826541 0.026 Uiso 1 1 d GR . . . .
N4 N 0.3885(4) 0.1268(3) 0.7673(3) 0.0193(6) Uani 1 1 d . . . . .
N5 N 0.3347(4) -0.0180(3) 0.7988(3) 0.0189(6) Uani 1 1 d . . . . .
H5 H 0.410340 -0.090708 0.799973 0.023 Uiso 1 1 calc R . . . .
N1 N 0.7259(4) 0.7654(3) 0.5748(3) 0.0201(6) Uani 1 1 d . . . . .
N7 N -0.1278(4) -0.0126(4) 0.8636(3) 0.0245(7) Uani 1 1 d . . . . .
C8 C 0.1625(4) -0.0421(4) 0.8273(3) 0.0159(7) Uani 1 1 d . . . . .
C4 C 0.7038(4) 0.3703(4) 0.5631(3) 0.0159(7) Uani 1 1 d . . . . .
C3 C 0.7504(4) 0.5185(4) 0.5229(3) 0.0183(7) Uani 1 1 d . . . . .
H3 H 0.822432 0.556704 0.438251 0.022 Uiso 1 1 calc R . . . .
C6 C 0.5546(4) 0.4038(4) 0.7735(3) 0.0176(7) Uani 1 1 d . . . . .
C7 C 0.5489(4) 0.1512(4) 0.7216(3) 0.0175(7) Uani 1 1 d . . . . .
H7 H 0.629878 0.073986 0.710183 0.021 Uiso 1 1 calc R . . . .
C1 C 0.5895(4) 0.5529(4) 0.7378(3) 0.0186(7) Uani 1 1 d . . . . .
H1 H 0.547622 0.615830 0.797997 0.022 Uiso 1 1 calc R . . . .
C5 C 0.6045(4) 0.3073(4) 0.6867(3) 0.0161(7) Uani 1 1 d . . . . .
C2 C 0.6866(4) 0.6071(4) 0.6126(3) 0.0174(7) Uani 1 1 d . . . . .
C9 C -0.0909(4) -0.1527(4) 0.8826(3) 0.0222(8) Uani 1 1 d . . . . .
H9 H -0.176309 -0.229212 0.908591 0.027 Uiso 1 1 calc 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 N3 1.229(4) . ?
O2 N3 1.223(4) . ?
O6 N1 1.245(4) . ?
O5 N1 1.213(4) . ?
O3 N2 1.223(4) . ?
O4 N2 1.220(4) . ?
N3 C6 1.475(4) . ?
N6 H6 0.8800 . ?
N6 N7 1.388(4) . ?
N6 C8 1.329(4) . ?
N8 N9 1.404(4) . ?
N8 C8 1.335(4) . ?
N8 C9 1.381(4) . ?
N2 C4 1.484(4) . ?
N9 H9A 0.8827 . ?
N9 H9B 0.8827 . ?
N4 N5 1.377(4) . ?
N4 C7 1.255(4) . ?
N5 H5 0.8800 . ?
N5 C8 1.330(4) . ?
N1 C2 1.469(4) . ?
N7 C9 1.307(5) . ?
C4 C3 1.392(5) . ?
C4 C5 1.384(5) . ?
C3 H3 0.9500 . ?
C3 C2 1.383(5) . ?
C6 C1 1.381(5) . ?
C6 C5 1.398(5) . ?
C7 H7 0.9500 . ?
C7 C5 1.479(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.371(5) . ?
C9 H9 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N3 C6 116.9(3) . . ?
O2 N3 O1 125.0(3) . . ?
O2 N3 C6 118.1(3) . . ?
N7 N6 H6 124.8 . . ?
C8 N6 H6 124.8 . . ?
C8 N6 N7 110.4(3) . . ?
C8 N8 N9 123.3(3) . . ?
C8 N8 C9 106.2(3) . . ?
C9 N8 N9 130.4(3) . . ?
O3 N2 C4 117.4(3) . . ?
O4 N2 O3 124.8(3) . . ?
O4 N2 C4 117.7(3) . . ?
N8 N9 H9A 109.4 . . ?
N8 N9 H9B 109.8 . . ?
H9A N9 H9B 109.2 . . ?
C7 N4 N5 116.7(3) . . ?
N4 N5 H5 121.8 . . ?
C8 N5 N4 116.5(3) . . ?
C8 N5 H5 121.8 . . ?
O6 N1 C2 117.2(3) . . ?
O5 N1 O6 124.8(3) . . ?
O5 N1 C2 118.0(3) . . ?
C9 N7 N6 104.3(3) . . ?
N6 C8 N8 107.8(3) . . ?
N6 C8 N5 127.9(3) . . ?
N5 C8 N8 124.3(3) . . ?
C3 C4 N2 117.0(3) . . ?
C5 C4 N2 118.7(3) . . ?
C5 C4 C3 124.4(3) . . ?
C4 C3 H3 121.7 . . ?
C2 C3 C4 116.6(3) . . ?
C2 C3 H3 121.7 . . ?
C1 C6 N3 115.9(3) . . ?
C1 C6 C5 123.7(3) . . ?
C5 C6 N3 120.3(3) . . ?
N4 C7 H7 121.9 . . ?
N4 C7 C5 116.1(3) . . ?
C5 C7 H7 121.9 . . ?
C6 C1 H1 121.1 . . ?
C2 C1 C6 117.7(3) . . ?
C2 C1 H1 121.1 . . ?
C4 C5 C6 114.8(3) . . ?
C4 C5 C7 122.3(3) . . ?
C6 C5 C7 122.7(3) . . ?
C3 C2 N1 119.4(3) . . ?
C1 C2 N1 118.0(3) . . ?
C1 C2 C3 122.6(3) . . ?
N8 C9 H9 124.3 . . ?
N7 C9 N8 111.4(3) . . ?
N7 C9 H9 124.3 . . ?

_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_mo_20181194-tjsxszcz_0m
_database_code_depnum_ccdc_archive 'CCDC 1900252'
loop_
_audit_author_name
_audit_author_address
'jie tang' 'Nanjing University of Science and Technology'
_audit_update_record             
;
2019-02-28 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;
_audit_creation_date             2018-12-17
_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(C8 H5 N9 O6), 0.5(H2 O2), 2(H2 O)'
_chemical_formula_sum            'C16 H15 N18 O15'
_chemical_formula_weight         699.46
_chemical_absolute_configuration .
_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      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   10.704(4)
_cell_length_b                   10.704
_cell_length_c                   23.932(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2742(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    454
_cell_measurement_temperature    153
_cell_measurement_theta_max      17.802
_cell_measurement_theta_min      2.553
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0846 before and 0.0662 after correction. The Ratio of minimum to maximum transmission is 0.7750. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1428
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1137
_diffrn_reflns_av_unetI/netI     0.1480
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7104
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.310
_diffrn_reflns_theta_min         2.691
_diffrn_ambient_temperature      153
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                1535
_reflns_number_total             2781
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.365
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         2781
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1337
_refine_ls_R_factor_gt           0.0617
_refine_ls_restrained_S_all      1.009
_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)+(0.0503P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1592
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0(4)
 1(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
3. Restrained distances
 N6-H6
 0.85 with sigma of 0.02
4. Others
 Fixed Sof: H10(0.5)
5.a Free rotating group:
 O10(H10), O11(H11A,H11B)
5.b Aromatic/amide H refined with riding coordinates:
 N5(H5), C7(H7), C2(H2), C6(H6A)
;
_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 0.3746(5) 0.6940(5) 0.3432(2) 0.0287(13) Uani 1 1 d . . . . .
O4 O 0.1657(5) 1.0692(5) 0.5541(2) 0.0331(14) Uani 1 1 d . . . . .
O6 O -0.0493(5) 0.6908(5) 0.5326(2) 0.0340(14) Uani 1 1 d . . . . .
O5 O -0.0194(5) 0.5716(5) 0.4617(3) 0.0352(15) Uani 1 1 d . . . . .
O3 O 0.3368(5) 1.1066(5) 0.5067(3) 0.0348(14) Uani 1 1 d . . . . .
N2 N 0.4100(6) 0.7300(6) 0.3897(3) 0.0236(15) Uani 1 1 d . . . . .
N4 N 0.2986(6) 0.4881(5) 0.4166(2) 0.0189(14) Uani 1 1 d . . . . .
O2 O 0.5203(5) 0.7466(6) 0.4031(2) 0.0396(15) Uani 1 1 d . . . . .
N5 N 0.2851(5) 0.3767(5) 0.3886(3) 0.0204(14) Uani 1 1 d . . . . .
H5 H 0.221568 0.364950 0.365856 0.024 Uiso 1 1 calc R . . . .
N3 N 0.0109(5) 0.6573(6) 0.4916(3) 0.0231(14) Uani 1 1 d . . . . .
N6 N 0.4791(5) 0.2956(6) 0.4228(3) 0.0215(14) Uani 1 1 d D . . . .
N8 N 0.4651(6) 0.1113(5) 0.3906(3) 0.0245(15) Uani 1 1 d . . . . .
N1 N 0.2482(6) 1.0404(6) 0.5193(3) 0.0275(16) Uani 1 1 d . . . . .
N7 N 0.5389(6) 0.1840(6) 0.4178(3) 0.0251(15) Uani 1 1 d . . . . .
N9 N 0.3576(5) 0.1693(5) 0.3756(3) 0.0226(14) Uani 1 1 d . . . . .
O10 O 0.6802(6) 0.6802(6) 0.500000 0.045(2) Uani 1 2 d S T P . .
H10 H 0.681196 0.745968 0.477935 0.067 Uiso 0.5 1 d G . . . .
O11 O 0.6648(6) 0.4484(6) 0.4470(3) 0.0517(19) Uani 1 1 d . . . . .
H11A H 0.693740 0.435366 0.413582 0.078 Uiso 1 1 d G . . . .
H11B H 0.666879 0.529197 0.450980 0.078 Uiso 1 1 d G . . . .
C8 C 0.3708(6) 0.2853(6) 0.3965(3) 0.0177(15) Uani 1 1 d . . . . .
C5 C 0.1228(6) 0.7315(6) 0.4777(3) 0.0194(16) Uani 1 1 d . . . . .
C4 C 0.2124(6) 0.6839(6) 0.4408(3) 0.0148(15) Uani 1 1 d . . . . .
C3 C 0.3148(6) 0.7655(6) 0.4316(3) 0.0191(16) Uani 1 1 d . . . . .
C7 C 0.2046(6) 0.5620(6) 0.4129(3) 0.0168(15) Uani 1 1 d . . . . .
H7 H 0.132021 0.538554 0.392571 0.020 Uiso 1 1 calc R . . . .
C2 C 0.3296(7) 0.8776(6) 0.4568(3) 0.0201(16) Uani 1 1 d . . . . .
H2 H 0.401652 0.927335 0.450270 0.024 Uiso 1 1 calc R . . . .
C6 C 0.1317(6) 0.8458(6) 0.5034(3) 0.0202(16) Uani 1 1 d . . . . .
H6A H 0.068441 0.875000 0.528001 0.024 Uiso 1 1 calc R . . . .
C1 C 0.2367(7) 0.9167(6) 0.4921(3) 0.0209(17) Uani 1 1 d . . . . .
H6 H 0.523(6) 0.363(4) 0.428(3) 0.03(2) Uiso 1 1 d 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 N2 1.237(8) . ?
O4 N1 1.252(8) . ?
O6 N3 1.228(8) . ?
O5 N3 1.208(7) . ?
O3 N1 1.223(8) . ?
N2 O2 1.237(7) . ?
N2 C3 1.479(9) . ?
N4 N5 1.376(7) . ?
N4 C7 1.283(8) . ?
N5 H5 0.8800 . ?
N5 C8 1.354(8) . ?
N3 C5 1.475(9) . ?
N6 N7 1.361(8) . ?
N6 C8 1.324(9) . ?
N6 H6 0.87(3) . ?
N8 N7 1.284(8) . ?
N8 N9 1.356(8) . ?
N1 C1 1.481(8) . ?
N9 C8 1.345(8) . ?
O10 H10 0.88(17) 7_556 ?
O10 H10 0.8805 . ?
O11 H11A 0.8699 . ?
O11 H11B 0.8702 . ?
C5 C4 1.400(9) . ?
C5 C6 1.373(9) . ?
C4 C3 1.419(9) . ?
C4 C7 1.468(9) . ?
C3 C2 1.352(10) . ?
C7 H7 0.9500 . ?
C2 H2 0.9500 . ?
C2 C1 1.369(10) . ?
C6 H6A 0.9500 . ?
C6 C1 1.383(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N2 O2 124.7(6) . . ?
O1 N2 C3 118.6(6) . . ?
O2 N2 C3 116.5(6) . . ?
C7 N4 N5 114.7(6) . . ?
N4 N5 H5 120.4 . . ?
C8 N5 N4 119.2(6) . . ?
C8 N5 H5 120.4 . . ?
O6 N3 C5 116.7(6) . . ?
O5 N3 O6 123.6(6) . . ?
O5 N3 C5 119.6(6) . . ?
N7 N6 H6 119(5) . . ?
C8 N6 N7 107.2(6) . . ?
C8 N6 H6 128(5) . . ?
N7 N8 N9 112.3(6) . . ?
O4 N1 C1 117.1(6) . . ?
O3 N1 O4 124.6(6) . . ?
O3 N1 C1 118.3(6) . . ?
N8 N7 N6 106.7(6) . . ?
C8 N9 N8 103.6(6) . . ?
H10 O10 H10 109.8 . 7_556 ?
H11A O11 H11B 104.5 . . ?
N6 C8 N5 126.8(7) . . ?
N6 C8 N9 110.2(6) . . ?
N9 C8 N5 123.0(6) . . ?
C4 C5 N3 120.2(6) . . ?
C6 C5 N3 115.8(6) . . ?
C6 C5 C4 124.0(6) . . ?
C5 C4 C3 113.8(6) . . ?
C5 C4 C7 124.9(6) . . ?
C3 C4 C7 121.4(6) . . ?
C4 C3 N2 118.7(6) . . ?
C2 C3 N2 116.7(6) . . ?
C2 C3 C4 124.6(7) . . ?
N4 C7 C4 118.1(6) . . ?
N4 C7 H7 120.9 . . ?
C4 C7 H7 120.9 . . ?
C3 C2 H2 121.3 . . ?
C3 C2 C1 117.4(6) . . ?
C1 C2 H2 121.3 . . ?
C5 C6 H6A 121.4 . . ?
C5 C6 C1 117.2(6) . . ?
C1 C6 H6A 121.4 . . ?
C2 C1 N1 119.0(6) . . ?
C2 C1 C6 122.9(6) . . ?
C6 C1 N1 118.1(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0(4)
2 1(4)

