# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_exp_8401
_database_code_depnum_ccdc_archive 'CCDC 2268477'
loop_
_audit_author_name
_audit_author_address
zhangchao
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-06-08 deposited with the CCDC.	2023-08-08 downloaded from the CCDC.
;
_audit_creation_date             2023-03-17
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C3 H2 N7 O, H4 N'
_chemical_formula_sum            'C3 H6 N8 O'
_chemical_formula_weight         170.16
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.5376(19)
_cell_length_b                   7.1964(15)
_cell_length_c                   11.685(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.27(3)
_cell_angle_gamma                90.00
_cell_volume                     692.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    471
_cell_measurement_temperature    115.75(10)
_cell_measurement_theta_max      26.3190
_cell_measurement_theta_min      3.7450
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_meas      1.632
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0979
_diffrn_reflns_av_unetI/netI     0.1058
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4671
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         3.36
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      115.75(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.8657
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -3.00   80.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289   37.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
  2 omega  -11.00   82.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289   77.0000  -90.0000 93

#__ type_ start__ end____ width___ exp.time_
  3 omega  -17.00   10.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.8508  -99.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega  -52.00   43.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  -77.0000  150.0000 95

#__ type_ start__ end____ width___ exp.time_
  5 omega  -76.00  -46.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.8508  -57.0000    0.0000 30

#__ type_ start__ end____ width___ exp.time_
  6 omega   -1.00   26.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  -99.0000  120.0000 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0368662000
_diffrn_orient_matrix_UB_12      0.0887636000
_diffrn_orient_matrix_UB_13      -0.0101322000
_diffrn_orient_matrix_UB_21      -0.0466848000
_diffrn_orient_matrix_UB_22      -0.0296583000
_diffrn_orient_matrix_UB_23      -0.0564000000
_diffrn_orient_matrix_UB_31      -0.0619596000
_diffrn_orient_matrix_UB_32      -0.0304020000
_diffrn_orient_matrix_UB_33      0.0255564000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                790
_reflns_number_total             1346
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1346
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1374
_refine_ls_R_factor_gt           0.0818
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0736P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1694
_refine_ls_wR_factor_ref         0.2002
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N7 N 0.7127(4) 0.5938(5) -0.0071(3) 0.0254(10) Uani 1 1 d . . .
H7A H 0.7619 0.6657 -0.0452 0.031 Uiso 1 1 d R . .
H7B H 0.6249 0.6439 0.0012 0.031 Uiso 1 1 d R . .
N1 N 1.0004(4) 0.0937(5) -0.1901(3) 0.0219(9) Uani 1 1 d . . .
O1 O 0.8240(3) 0.3435(4) -0.0809(3) 0.0219(8) Uani 1 1 d . . .
N8 N 1.0934(4) 0.4402(5) -0.2742(3) 0.0255(10) Uani 1 1 d . . .
H8A H 1.0676 0.3425 -0.2408 0.031 Uiso 1 1 d R . .
H8B H 1.0710 0.5377 -0.2390 0.031 Uiso 1 1 d R . .
H8C H 1.1958 0.4381 -0.2694 0.031 Uiso 1 1 d R . .
H8D H 1.0395 0.4424 -0.3476 0.031 Uiso 1 1 d R . .
N4 N 0.8814(4) -0.1515(5) -0.1334(3) 0.0243(9) Uani 1 1 d . . .
N6 N 0.6219(4) 0.2814(5) -0.0003(3) 0.0247(9) Uani 1 1 d . . .
C1 C 0.8900(4) 0.0337(6) -0.1362(4) 0.0181(10) Uani 1 1 d . . .
N2 N 1.0634(4) -0.0626(5) -0.2227(3) 0.0234(9) Uani 1 1 d . . .
C2 C 0.7935(5) 0.1556(6) -0.0840(4) 0.0203(10) Uani 1 1 d . . .
N5 N 0.6754(4) 0.1139(5) -0.0380(3) 0.0243(9) Uani 1 1 d . . .
C3 C 0.7122(4) 0.4115(6) -0.0272(4) 0.0223(11) Uani 1 1 d . . .
N3 N 0.9940(4) -0.2080(5) -0.1890(3) 0.0244(9) 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
N7 H7A 0.8599 . ?
N7 H7B 0.8600 . ?
N7 C3 1.333(5) . ?
N1 C1 1.336(5) . ?
N1 N2 1.344(5) . ?
O1 C2 1.376(5) . ?
O1 C3 1.364(5) . ?
N8 H8A 0.8603 . ?
N8 H8B 0.8601 . ?
N8 H8C 0.8606 . ?
N8 H8D 0.8607 . ?
N4 C1 1.336(5) . ?
N4 N3 1.356(5) . ?
N6 N5 1.401(5) . ?
N6 C3 1.303(5) . ?
C1 C2 1.444(6) . ?
N2 N3 1.313(5) . ?
C2 N5 1.296(5) . ?

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
H7A N7 H7B 111.4 . . ?
C3 N7 H7A 118.7 . . ?
C3 N7 H7B 118.0 . . ?
C1 N1 N2 104.3(3) . . ?
C3 O1 C2 102.3(3) . . ?
H8A N8 H8B 109.5 . . ?
H8A N8 H8C 109.5 . . ?
H8A N8 H8D 109.5 . . ?
H8B N8 H8C 109.5 . . ?
H8B N8 H8D 109.5 . . ?
H8C N8 H8D 109.4 . . ?
C1 N4 N3 103.7(3) . . ?
C3 N6 N5 106.3(4) . . ?
N1 C1 C2 123.7(4) . . ?
N4 C1 N1 112.6(4) . . ?
N4 C1 C2 123.7(4) . . ?
N3 N2 N1 109.7(3) . . ?
O1 C2 C1 118.8(4) . . ?
N5 C2 O1 112.3(4) . . ?
N5 C2 C1 128.8(4) . . ?
C2 N5 N6 106.5(3) . . ?
N7 C3 O1 117.6(4) . . ?
N6 C3 N7 129.8(4) . . ?
N6 C3 O1 112.6(4) . . ?
N2 N3 N4 109.7(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
N1 C1 C2 O1 -5.2(6) . . . . ?
N1 C1 C2 N5 174.1(4) . . . . ?
N1 N2 N3 N4 0.4(4) . . . . ?
O1 C2 N5 N6 -0.4(4) . . . . ?
N4 C1 C2 O1 173.2(4) . . . . ?
N4 C1 C2 N5 -7.5(7) . . . . ?
C1 N1 N2 N3 -0.3(4) . . . . ?
C1 N4 N3 N2 -0.3(4) . . . . ?
C1 C2 N5 N6 -179.8(4) . . . . ?
N2 N1 C1 N4 0.1(4) . . . . ?
N2 N1 C1 C2 178.6(3) . . . . ?
C2 O1 C3 N7 178.0(3) . . . . ?
C2 O1 C3 N6 -0.2(4) . . . . ?
N5 N6 C3 N7 -178.0(4) . . . . ?
N5 N6 C3 O1 0.0(4) . . . . ?
C3 O1 C2 C1 179.8(3) . . . . ?
C3 O1 C2 N5 0.4(4) . . . . ?
C3 N6 N5 C2 0.3(4) . . . . ?
N3 N4 C1 N1 0.1(4) . . . . ?
N3 N4 C1 C2 -178.4(3) . . . . ?

####################################################################### 
# 
# 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_230102a
_database_code_depnum_ccdc_archive 'CCDC 2268481'
loop_
_audit_author_name
_audit_author_address
'Chao Zhang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-06-08 deposited with the CCDC.	2023-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H7 N9 O'
_chemical_formula_weight         185.18

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   3.6710(5)
_cell_length_b                   13.8594(13)
_cell_length_c                   15.5980(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.269(2)
_cell_angle_gamma                90.00
_cell_volume                     793.40(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1414
_cell_measurement_theta_min      2.605
_cell_measurement_theta_max      27.099

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      1.550
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9517
_exptl_absorpt_correction_T_max  0.9963
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3806
_diffrn_reflns_av_R_equivalents  0.0763
_diffrn_reflns_av_sigmaI/netI    0.0668
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         25.02
_reflns_number_total             1402
_reflns_number_gt                1061
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1130P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1402
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.1811
_refine_ls_wR_factor_gt          0.1660
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5327(7) 0.30750(16) 0.04560(14) 0.0351(7) Uani 1 1 d . . .
N2 N 0.6472(7) 0.37862(15) 0.10664(14) 0.0344(7) Uani 1 1 d . . .
N3 N 0.5770(9) 0.13504(16) 0.04898(16) 0.0473(8) Uani 1 1 d . . .
H3A H 0.4697 0.1268 0.0000 0.057 Uiso 1 1 calc R . .
H3B H 0.6523 0.0860 0.0781 0.057 Uiso 1 1 calc R . .
N4 N 1.1126(7) 0.31663(17) 0.31195(14) 0.0338(6) Uani 1 1 d . . .
N5 N 1.2099(7) 0.38062(16) 0.37469(15) 0.0380(7) Uani 1 1 d . . .
N6 N 1.1095(7) 0.46872(17) 0.35148(15) 0.0384(7) Uani 1 1 d . . .
N7 N 0.9445(7) 0.46574(16) 0.27276(14) 0.0345(7) Uani 1 1 d . . .
N8 N 0.3566(7) 0.11880(15) 0.33528(16) 0.0362(7) Uani 1 1 d . . .
H8A H 0.3165 0.1795 0.3192 0.054 Uiso 1 1 calc R . .
H8B H 0.3244 0.0798 0.2904 0.054 Uiso 1 1 calc R . .
H8C H 0.5841 0.1131 0.3556 0.054 Uiso 1 1 calc R . .
N9 N 0.1033(7) 0.09256(16) 0.40176(15) 0.0357(6) Uani 1 1 d . . .
H9A H 0.1431 0.1299 0.4474 0.053 Uiso 1 1 d R . .
H9B H 0.1382 0.0311 0.4162 0.053 Uiso 1 1 d R . .
O1 O 0.7923(6) 0.23324(13) 0.15950(12) 0.0331(6) Uani 1 1 d . . .
C1 C 0.6266(8) 0.22353(19) 0.07973(16) 0.0299(7) Uani 1 1 d . . .
C2 C 0.7950(8) 0.33291(19) 0.17091(16) 0.0296(7) Uani 1 1 d . . .
C3 C 0.9526(8) 0.37114(18) 0.25122(16) 0.0289(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.322(3) . ?
N1 N2 1.427(3) . ?
N2 C2 1.295(3) . ?
N3 C1 1.328(3) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 C3 1.337(3) . ?
N4 N5 1.362(3) . ?
N5 N6 1.324(3) . ?
N6 N7 1.358(3) . ?
N7 C3 1.354(3) . ?
N8 N9 1.454(3) . ?
N8 H8A 0.8900 . ?
N8 H8B 0.8900 . ?
N8 H8C 0.8900 . ?
N9 H9A 0.8900 . ?
N9 H9B 0.8900 . ?
O1 C1 1.379(3) . ?
O1 C2 1.393(3) . ?
C2 C3 1.467(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
C1 N1 N2 105.6(2) . . ?
C2 N2 N1 106.9(2) . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C3 N4 N5 104.2(2) . . ?
N6 N5 N4 109.7(2) . . ?
N5 N6 N7 109.6(2) . . ?
C3 N7 N6 104.0(2) . . ?
N9 N8 H8A 109.5 . . ?
N9 N8 H8B 109.5 . . ?
H8A N8 H8B 109.5 . . ?
N9 N8 H8C 109.5 . . ?
H8A N8 H8C 109.5 . . ?
H8B N8 H8C 109.5 . . ?
N8 N9 H9A 109.2 . . ?
N8 N9 H9B 109.2 . . ?
H9A N9 H9B 109.5 . . ?
C1 O1 C2 102.3(2) . . ?
N1 C1 N3 129.4(3) . . ?
N1 C1 O1 112.5(2) . . ?
N3 C1 O1 118.0(2) . . ?
N2 C2 O1 112.6(2) . . ?
N2 C2 C3 129.4(3) . . ?
O1 C2 C3 118.0(2) . . ?
N4 C3 N7 112.5(2) . . ?
N4 C3 C2 124.0(2) . . ?
N7 C3 C2 123.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C2 -0.3(3) . . . . ?
C3 N4 N5 N6 0.2(3) . . . . ?
N4 N5 N6 N7 -0.3(3) . . . . ?
N5 N6 N7 C3 0.2(3) . . . . ?
N2 N1 C1 N3 179.2(3) . . . . ?
N2 N1 C1 O1 0.6(3) . . . . ?
C2 O1 C1 N1 -0.6(3) . . . . ?
C2 O1 C1 N3 -179.4(3) . . . . ?
N1 N2 C2 O1 -0.1(3) . . . . ?
N1 N2 C2 C3 -179.1(3) . . . . ?
C1 O1 C2 N2 0.4(3) . . . . ?
C1 O1 C2 C3 179.5(2) . . . . ?
N5 N4 C3 N7 -0.1(3) . . . . ?
N5 N4 C3 C2 -178.7(3) . . . . ?
N6 N7 C3 N4 -0.1(3) . . . . ?
N6 N7 C3 C2 178.6(3) . . . . ?
N2 C2 C3 N4 -177.1(3) . . . . ?
O1 C2 C3 N4 4.0(4) . . . . ?
N2 C2 C3 N7 4.4(5) . . . . ?
O1 C2 C3 N7 -174.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.084
####################################################################### 
# 
# 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_exp_8399
_database_code_depnum_ccdc_archive 'CCDC 2268490'
loop_
_audit_author_name
_audit_author_address
'Chao Zhang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-06-08 deposited with the CCDC.	2023-08-08 downloaded from the CCDC.
;
_audit_creation_date             2023-03-17
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C3 N7 O), 2(Ca0.5 H6 O3), 2(H2 O)'
_chemical_formula_sum            'C6 H16 Ca N14 O10'
_chemical_formula_weight         484.41
_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'
Ca Ca 0.2262 0.3064 '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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   5.5630(5)
_cell_length_b                   9.2316(8)
_cell_length_c                   10.4531(11)
_cell_angle_alpha                102.789(8)
_cell_angle_beta                 98.212(8)
_cell_angle_gamma                104.552(8)
_cell_volume                     495.39(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    794
_cell_measurement_temperature    115.70(10)
_cell_measurement_theta_max      24.1780
_cell_measurement_theta_min      3.8680
_exptl_absorpt_coefficient_mu    0.397
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_meas      1.624
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod-shaped
_exptl_crystal_F_000             250
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0809
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3305
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.52
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      115.70(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.8175
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -51.00   43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2414  -77.0000 -120.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega  -13.00   15.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2414  -99.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega  -15.00   28.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.0070  -99.0000   30.0000 43

#__ type_ start__ end____ width___ exp.time_
  4 omega  -10.00   84.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2414   77.0000    0.0000 94

#__ type_ start__ end____ width___ exp.time_
  5 omega    1.00   84.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2414   57.0000  150.0000 83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1137135000
_diffrn_orient_matrix_UB_12      0.0400471000
_diffrn_orient_matrix_UB_13      0.0486941000
_diffrn_orient_matrix_UB_21      -0.0536172000
_diffrn_orient_matrix_UB_22      -0.0334350000
_diffrn_orient_matrix_UB_23      0.0481612000
_diffrn_orient_matrix_UB_31      0.0484756000
_diffrn_orient_matrix_UB_32      -0.0637909000
_diffrn_orient_matrix_UB_33      -0.0193623000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1387
_reflns_number_total             1903
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1903
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0582
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0680P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1577
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1086(4) 0.1931(3) 0.1305(2) 0.0269(6) Uani 1 1 d . . .
N1 N -0.5217(6) 0.0602(3) -0.0135(3) 0.0270(7) Uani 1 1 d . . .
N3 N -0.0984(5) 0.4333(3) 0.1219(3) 0.0260(7) Uani 1 1 d . . .
N5 N 0.6046(5) 0.3615(3) 0.3620(3) 0.0272(7) Uani 1 1 d . . .
C3 C 0.2734(6) 0.3878(4) 0.2538(3) 0.0225(8) Uani 1 1 d . . .
N6 N 0.6382(5) 0.5108(3) 0.3734(3) 0.0275(7) Uani 1 1 d . . .
C2 C 0.0239(6) 0.3467(4) 0.1705(3) 0.0235(8) Uani 1 1 d . . .
N7 N 0.4335(5) 0.5322(3) 0.3054(3) 0.0258(7) Uani 1 1 d . . .
C1 C -0.3231(6) 0.1933(4) 0.0516(4) 0.0275(8) Uani 1 1 d . . .
N4 N 0.3745(5) 0.2806(3) 0.2875(3) 0.0251(7) Uani 1 1 d . . .
N2 N -0.3280(5) 0.3303(3) 0.0436(3) 0.0278(7) Uani 1 1 d . . .
Ca Ca 1.0000 1.0000 0.5000 0.0242(3) Uani 1 2 d S . .
O3 O 0.5973(4) 0.8671(3) 0.3735(3) 0.0331(6) Uani 1 1 d . . .
H3A H 0.5404 0.7689 0.3431 0.050 Uiso 1 1 d R . .
H3B H 0.4817 0.9077 0.3517 0.050 Uiso 1 1 d R . .
O4 O 1.1794(4) 0.9802(3) 0.3106(2) 0.0303(6) Uani 1 1 d . . .
H4A H 1.0862 0.9124 0.2406 0.045 Uiso 1 1 d R . .
H4B H 1.2376 1.0651 0.2912 0.045 Uiso 1 1 d R . .
O2 O 1.0535(5) 0.7665(3) 0.5056(2) 0.0325(6) Uani 1 1 d . . .
H2A H 0.9382 0.6808 0.4700 0.049 Uiso 1 1 d R . .
H2B H 1.1800 0.7500 0.5496 0.049 Uiso 1 1 d R . .
O5 O -0.1111(5) 0.7374(3) 0.1113(3) 0.0348(7) Uani 1 1 d . . .
H5A H -0.2680 0.7276 0.0865 0.052 Uiso 1 1 d R . .
H5B H -0.0908 0.6483 0.1067 0.052 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 C2 1.361(4) . ?
O1 C1 1.350(4) . ?
N1 N1 1.277(5) 2_455 ?
N1 C1 1.388(4) . ?
N3 C2 1.309(4) . ?
N3 N2 1.397(4) . ?
N5 N6 1.320(4) . ?
N5 N4 1.334(4) . ?
C3 C2 1.440(5) . ?
C3 N7 1.345(4) . ?
C3 N4 1.340(4) . ?
N6 N7 1.336(4) . ?
C1 N2 1.293(4) . ?
Ca O3 2.308(2) . ?
Ca O3 2.308(2) 2_776 ?
Ca O4 2.333(2) 2_776 ?
Ca O4 2.333(2) . ?
Ca O2 2.261(2) 2_776 ?
Ca O2 2.261(2) . ?
O3 H3A 0.8500 . ?
O3 H3B 0.8499 . ?
O4 H4A 0.8501 . ?
O4 H4B 0.8500 . ?
O2 H2A 0.8501 . ?
O2 H2B 0.8499 . ?
O5 H5A 0.8500 . ?
O5 H5B 0.8501 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C2 102.0(3) . . ?
N1 N1 C1 111.5(4) 2_455 . ?
C2 N3 N2 105.4(3) . . ?
N6 N5 N4 109.3(3) . . ?
N7 C3 C2 126.1(3) . . ?
N4 C3 C2 122.1(3) . . ?
N4 C3 N7 111.8(3) . . ?
N5 N6 N7 110.2(3) . . ?
O1 C2 C3 116.6(3) . . ?
N3 C2 O1 112.9(3) . . ?
N3 C2 C3 130.5(3) . . ?
N6 N7 C3 103.9(3) . . ?
O1 C1 N1 123.7(3) . . ?
N2 C1 O1 113.5(3) . . ?
N2 C1 N1 122.8(3) . . ?
N5 N4 C3 104.7(3) . . ?
C1 N2 N3 106.3(3) . . ?
O3 Ca O3 180.0 2_776 . ?
O3 Ca O4 87.61(9) . 2_776 ?
O3 Ca O4 92.39(8) 2_776 2_776 ?
O3 Ca O4 87.61(9) 2_776 . ?
O3 Ca O4 92.39(8) . . ?
O4 Ca O4 180.000(1) 2_776 . ?
O2 Ca O3 92.61(9) 2_776 . ?
O2 Ca O3 87.39(9) . . ?
O2 Ca O3 87.39(9) 2_776 2_776 ?
O2 Ca O3 92.61(9) . 2_776 ?
O2 Ca O4 87.15(8) . . ?
O2 Ca O4 87.15(8) 2_776 2_776 ?
O2 Ca O4 92.85(8) . 2_776 ?
O2 Ca O4 92.85(8) 2_776 . ?
O2 Ca O2 180.000(1) 2_776 . ?
Ca O3 H3A 124.8 . . ?
Ca O3 H3B 125.8 . . ?
H3A O3 H3B 109.3 . . ?
Ca O4 H4A 114.9 . . ?
Ca O4 H4B 115.6 . . ?
H4A O4 H4B 109.3 . . ?
Ca O2 H2A 123.4 . . ?
Ca O2 H2B 126.9 . . ?
H2A O2 H2B 109.3 . . ?
H5A O5 H5B 109.3 . . ?

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
O1 C1 N2 N3 0.6(4) . . . . ?
N1 N1 C1 O1 1.8(5) 2_455 . . . ?
N1 N1 C1 N2 -177.3(4) 2_455 . . . ?
N1 C1 N2 N3 179.8(3) . . . . ?
N5 N6 N7 C3 0.8(4) . . . . ?
N6 N5 N4 C3 0.7(3) . . . . ?
C2 O1 C1 N1 -179.9(3) . . . . ?
C2 O1 C1 N2 -0.7(4) . . . . ?
C2 N3 N2 C1 -0.2(3) . . . . ?
C2 C3 N7 N6 -179.5(3) . . . . ?
C2 C3 N4 N5 179.0(3) . . . . ?
N7 C3 C2 O1 -179.1(3) . . . . ?
N7 C3 C2 N3 3.2(6) . . . . ?
N7 C3 N4 N5 -0.2(4) . . . . ?
C1 O1 C2 N3 0.5(4) . . . . ?
C1 O1 C2 C3 -177.6(3) . . . . ?
N4 N5 N6 N7 -0.9(4) . . . . ?
N4 C3 C2 O1 1.9(5) . . . . ?
N4 C3 C2 N3 -175.8(3) . . . . ?
N4 C3 N7 N6 -0.4(4) . . . . ?
N2 N3 C2 O1 -0.2(4) . . . . ?
N2 N3 C2 C3 177.5(3) . . . . ?

####################################################################### 
# 
# 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_exp_8318
_database_code_depnum_ccdc_archive 'CCDC 2268480'
loop_
_audit_author_name
_audit_author_address
'Chao Zhang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-06-08 deposited with the CCDC.	2023-08-08 downloaded from the CCDC.
;
_audit_creation_date             2023-06-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C3 H2 N7 O, H2 O, H4 N O'
_chemical_formula_sum            'C3 H8 N8 O3'
_chemical_formula_weight         204.149
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   6.8816(6)
_cell_length_b                   16.816(2)
_cell_length_c                   7.3514(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.342(8)
_cell_angle_gamma                90
_cell_volume                     848.27(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    623
_cell_measurement_temperature    117.65(10)
_cell_measurement_theta_max      24.8220
_cell_measurement_theta_min      3.6810
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             424.389
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.1060
_diffrn_reflns_Laue_measured_fraction_full 0.9980
_diffrn_reflns_Laue_measured_fraction_max 0.9731
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3517
_diffrn_reflns_point_group_measured_fraction_full 0.9980
_diffrn_reflns_point_group_measured_fraction_max 0.9731
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.03
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      117.65(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9980
_diffrn_measured_fraction_theta_max 0.9731
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   16.00   84.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289   19.0000   90.0000 68

#__ type_ start__ end____ width___ exp.time_
  2 omega  -29.00   31.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  -77.0000  -30.0000 60

#__ type_ start__ end____ width___ exp.time_
  3 omega  -24.00   22.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.8508  -99.0000 -180.0000 46

#__ type_ start__ end____ width___ exp.time_
  4 omega   62.00   88.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  178.0000 -150.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0002826000
_diffrn_orient_matrix_UB_12      0.0382539000
_diffrn_orient_matrix_UB_13      0.0407841000
_diffrn_orient_matrix_UB_21      0.0543582000
_diffrn_orient_matrix_UB_22      -0.0151109000
_diffrn_orient_matrix_UB_23      0.0782635000
_diffrn_orient_matrix_UB_31      0.0878578000
_diffrn_orient_matrix_UB_32      0.0094674000
_diffrn_orient_matrix_UB_33      -0.0396613000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              5
_reflns_limit_h_min              -8
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              -5
_reflns_number_gt                1059
_reflns_number_total             1625
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.5300
_refine_diff_density_min         -0.6017
_refine_diff_density_rms         0.1460
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             6.7196
_refine_ls_goodness_of_fit_ref   1.0634
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    11
_refine_ls_number_parameters     135
_refine_ls_number_reflns         1625
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0635
_refine_ls_restrained_S_all      1.0624
_refine_ls_shift/su_max          -0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+0.0092P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1531
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H) groups, All O(H) groups
2. Restrained distances
 O3-H3a = O3-H3b
 0.85 with sigma of 0.01
 H3b-H3a
 1.387 with sigma of 0.02
3.a X=CH2 refined with riding coordinates:
 N7(H7a,H7b)
3.b Idealised Me refined as rotating group:
 N8(H8a,H8b,H8c)
3.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O1 O 0.2783(3) 0.52548(14) 0.2021(3) 0.0180(6) Uani 1.000000 .
O3 O 0.5337(3) 0.71256(15) -0.2800(3) 0.0214(6) Uani 1.000000 D
N2 N 0.0927(4) 0.37153(18) -0.2108(4) 0.0189(7) Uani 1.000000 .
N3 N 0.1366(4) 0.41585(18) -0.3502(4) 0.0206(7) Uani 1.000000 .
N8 N 0.0909(4) 0.33784(18) 0.2953(3) 0.0212(7) Uani 1.000000 .
H8a H 0.0921(16) 0.3709(8) 0.3934(15) 0.0254(9) Uiso 1.000000 GR
H8b H 0.2019(4) 0.30821(19) 0.302(3) 0.0254(9) Uiso 1.000000 GR
H8c H 0.0841(15) 0.3672(9) 0.1910(13) 0.0254(9) Uiso 1.000000 GR
O2 O -0.0726(3) 0.28697(16) 0.2942(4) 0.0325(7) Uani 1.000000 .
H2 H -0.0351(4) 0.23942(17) 0.297(6) 0.0487(11) Uiso 1.000000 GR
N5 N 0.3617(4) 0.60882(18) -0.0129(3) 0.0178(7) Uani 1.000000 .
N6 N 0.4051(4) 0.64460(18) 0.1585(3) 0.0173(7) Uani 1.000000 .
N4 N 0.2149(4) 0.48507(18) -0.2893(4) 0.0198(7) Uani 1.000000 .
N1 N 0.1392(4) 0.41055(18) -0.0545(4) 0.0177(7) Uani 1.000000 .
N7 N 0.3660(4) 0.59903(19) 0.4592(4) 0.0233(7) Uani 1.000000 .
H7a H 0.3268(4) 0.55954(19) 0.5260(4) 0.0280(9) Uiso 1.000000 R
H7b H 0.4140(4) 0.64245(19) 0.5122(4) 0.0280(9) Uiso 1.000000 R
C1 C 0.2144(4) 0.4794(2) -0.1069(4) 0.0149(8) Uani 1.000000 .
C3 C 0.3529(4) 0.5932(2) 0.2804(4) 0.0171(8) Uani 1.000000 .
C2 C 0.2875(4) 0.5402(2) 0.0185(4) 0.0148(8) Uani 1.000000 .
H3a H 0.474(4) 0.6881(15) -0.199(3) 0.0222(12) Uiso 1.000000 DR
H3b H 0.492(5) 0.7604(8) -0.284(4) 0.0222(12) Uiso 1.000000 DR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.358(4) . ?
O1 C2 1.378(4) . ?
O3 H3a 0.852(9) . ?
O3 H3b 0.855(9) . ?
N2 N3 1.321(4) . ?
N2 N1 1.341(4) . ?
N3 N4 1.345(4) . ?
N8 H8a 0.9100 . ?
N8 H8b 0.9100 . ?
N8 H8c 0.9100 . ?
N8 O2 1.413(3) . ?
O2 H2 0.8400 . ?
N5 N6 1.408(4) . ?
N5 C2 1.290(4) . ?
N6 C3 1.315(4) . ?
N4 C1 1.345(4) . ?
N1 C1 1.337(4) . ?
N7 H7a 0.8800 . ?
N7 H7b 0.8800 . ?
N7 C3 1.315(4) . ?
C1 C2 1.441(5) . ?

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 O1 C3 102.8(3) . . ?
H3b O3 H3a 108(2) . . ?
N1 N2 N3 109.6(3) . . ?
N4 N3 N2 109.8(3) . . ?
H8b N8 H8a 109.5 . . ?
H8c N8 H8a 109.5 . . ?
H8c N8 H8b 109.5 . . ?
O2 N8 H8a 109.5 . . ?
O2 N8 H8b 109.5 . . ?
O2 N8 H8c 109.5 . . ?
H2 O2 N8 109.5 . . ?
C2 N5 N6 106.4(3) . . ?
C3 N6 N5 106.2(3) . . ?
C1 N4 N3 103.8(3) . . ?
C1 N1 N2 104.4(3) . . ?
H7b N7 H7a 120.0 . . ?
C3 N7 H7a 120.0 . . ?
C3 N7 H7b 120.0 . . ?
N1 C1 N4 112.3(3) . . ?
C2 C1 N4 124.1(3) . . ?
C2 C1 N1 123.6(3) . . ?
N6 C3 O1 112.1(3) . . ?
N7 C3 O1 118.8(3) . . ?
N7 C3 N6 129.1(3) . . ?
N5 C2 O1 112.6(3) . . ?
C1 C2 O1 117.4(3) . . ?
C1 C2 N5 130.1(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
O1 C3 N6 N5 0.2(3) . . . . ?
O1 C2 N5 N6 -0.6(3) . . . . ?
O1 C2 C1 N4 -179.6(3) . . . . ?
O1 C2 C1 N1 -0.0(3) . . . . ?
N2 N3 N4 C1 -0.2(3) . . . . ?
N2 N1 C1 N4 0.5(2) . . . . ?
N2 N1 C1 C2 -179.1(2) . . . . ?
N3 N4 C1 N1 -0.2(3) . . . . ?
N3 N4 C1 C2 179.3(2) . . . . ?
N5 N6 C3 N7 179.3(2) . . . . ?
N5 C2 C1 N4 1.0(4) . . . . ?
N5 C2 C1 N1 -179.4(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
O3 H3a 1 0.8500 0.0100 -0.0024
O3 H3b 1 0.8500 0.0100 -0.0047
H3b H3a 1 1.3870 0.0200 0.0096

