# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_22019312_0m
_database_code_depnum_ccdc_archive 'CCDC 1909774'
loop_
_audit_author_name
_audit_author_address
'jie Tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-03-04 deposited with the CCDC.	2020-03-10 downloaded from the CCDC.
;
_audit_creation_date             2020-03-04
_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, C6 H9 N8 O2'
_chemical_formula_sum            'C6 H9 Cl N8 O2'
_chemical_formula_weight         260.66
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.8258(2)
_cell_length_b                   23.6441(9)
_cell_length_c                   7.0643(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.5760(10)
_cell_angle_gamma                90
_cell_volume                     1080.71(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4931
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.493
_cell_measurement_theta_min      3.162
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.906
_exptl_absorpt_coefficient_mu    0.361
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1181 before and 0.0657 after correction. The Ratio of minimum to maximum transmission is 0.8754. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12802
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         3.162
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2018
_reflns_number_total             2473
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2473
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      1.169
_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)+(0.0142P)²+1.4562P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0976
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N6-H6B = N6-H6A
 0.86 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N7(H7), N4(H4), C4(H4A), C6(H6)
3.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_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 0.22017(9) 0.43157(3) 0.99363(8) 0.01586(15) Uani 1 1 d . . . . .
O2 O 0.8952(3) 0.30879(8) 0.6858(3) 0.0198(4) Uani 1 1 d . . . . .
O1 O 0.9385(3) 0.29026(8) 1.0157(3) 0.0253(4) Uani 1 1 d . . . . .
N7 N -0.0686(3) 0.43702(9) 0.5706(3) 0.0149(4) Uani 1 1 d . . . . .
H7 H 0.029440 0.429535 0.683392 0.018 Uiso 1 1 calc R . . . .
N5 N -0.2387(3) 0.44130(8) 0.2588(3) 0.0141(4) Uani 1 1 d . . . . .
N3 N 0.2388(3) 0.36923(8) 0.4934(3) 0.0140(4) Uani 1 1 d . . . . .
N4 N 0.0668(3) 0.38721(9) 0.3427(3) 0.0158(4) Uani 1 1 d . . . . .
H4 H 0.046811 0.377488 0.217666 0.019 Uiso 1 1 calc R . . . .
N6 N -0.2857(3) 0.43141(10) 0.0519(3) 0.0171(4) Uani 1 1 d D . . . .
N8 N -0.2445(3) 0.46845(9) 0.5554(3) 0.0181(5) Uani 1 1 d . . . . .
N2 N 0.7325(3) 0.32343(9) 0.5211(3) 0.0175(5) Uani 1 1 d . . . . .
N1 N 0.8134(3) 0.30305(9) 0.8516(3) 0.0170(4) Uani 1 1 d . . . . .
C4 C 0.3753(4) 0.34493(10) 0.4332(3) 0.0146(5) Uani 1 1 d . . . . .
H4A H 0.350910 0.338881 0.294604 0.018 Uiso 1 1 calc R . . . .
C3 C 0.5683(4) 0.32659(10) 0.5785(4) 0.0138(5) Uani 1 1 d . . . . .
C5 C -0.0683(4) 0.41982(10) 0.3925(3) 0.0135(5) Uani 1 1 d . . . . .
C6 C -0.3421(4) 0.47065(10) 0.3652(4) 0.0163(5) Uani 1 1 d . . . . .
H6 H -0.468855 0.490084 0.306918 0.020 Uiso 1 1 calc R . . . .
C1 C 0.6132(4) 0.31291(10) 0.7838(4) 0.0146(5) Uani 1 1 d . . . . .
C2 C 0.4801(4) 0.30359(12) 0.9107(4) 0.0215(6) Uani 1 1 d . . . . .
H2A H 0.407106 0.267488 0.875001 0.032 Uiso 1 1 calc GR . . . .
H2B H 0.379299 0.334389 0.889528 0.032 Uiso 1 1 calc GR . . . .
H2C H 0.565841 0.302739 1.051385 0.032 Uiso 1 1 calc GR . . . .
H6A H -0.420(3) 0.4275(11) 0.009(4) 0.018(7) Uiso 1 1 d D . . . .
H6B H -0.251(5) 0.4626(10) 0.002(4) 0.033(9) 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
O2 N2 1.373(3) . ?
O2 N1 1.456(3) . ?
O1 N1 1.238(3) . ?
N7 H7 0.8800 . ?
N7 N8 1.387(3) . ?
N7 C5 1.323(3) . ?
N5 N6 1.413(3) . ?
N5 C5 1.343(3) . ?
N5 C6 1.372(3) . ?
N3 N4 1.377(3) . ?
N3 C4 1.278(3) . ?
N4 H4 0.8800 . ?
N4 C5 1.333(3) . ?
N6 H6A 0.876(17) . ?
N6 H6B 0.883(18) . ?
N8 C6 1.297(3) . ?
N2 C3 1.310(3) . ?
N1 C1 1.317(3) . ?
C4 H4A 0.9500 . ?
C4 C3 1.455(3) . ?
C3 C1 1.421(3) . ?
C6 H6 0.9500 . ?
C1 C2 1.482(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 O2 N1 106.93(16) . . ?
N8 N7 H7 124.6 . . ?
C5 N7 H7 124.6 . . ?
C5 N7 N8 110.77(19) . . ?
C5 N5 N6 121.7(2) . . ?
C5 N5 C6 106.72(19) . . ?
C6 N5 N6 131.6(2) . . ?
C4 N3 N4 114.43(19) . . ?
N3 N4 H4 121.1 . . ?
C5 N4 N3 117.73(19) . . ?
C5 N4 H4 121.1 . . ?
N5 N6 H6A 104.2(18) . . ?
N5 N6 H6B 106(2) . . ?
H6A N6 H6B 110(3) . . ?
C6 N8 N7 104.4(2) . . ?
C3 N2 O2 107.03(19) . . ?
O1 N1 O2 116.68(19) . . ?
O1 N1 C1 135.2(2) . . ?
C1 N1 O2 108.07(18) . . ?
N3 C4 H4A 120.3 . . ?
N3 C4 C3 119.4(2) . . ?
C3 C4 H4A 120.3 . . ?
N2 C3 C4 118.0(2) . . ?
N2 C3 C1 112.1(2) . . ?
C1 C3 C4 129.8(2) . . ?
N7 C5 N5 106.8(2) . . ?
N7 C5 N4 129.8(2) . . ?
N4 C5 N5 123.4(2) . . ?
N5 C6 H6 124.3 . . ?
N8 C6 N5 111.3(2) . . ?
N8 C6 H6 124.3 . . ?
N1 C1 C3 105.9(2) . . ?
N1 C1 C2 121.2(2) . . ?
C3 C1 C2 132.6(2) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_22019404_0m_4
_database_code_depnum_ccdc_archive 'CCDC 1918709'
loop_
_audit_author_name
_audit_author_address
'jie Tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-03-04 deposited with the CCDC.	2020-03-10 downloaded from the CCDC.
;
_audit_creation_date             2020-03-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H8 N8 O2, C6 H9 N8 O2, N3 O4'
_chemical_formula_sum            'C12 H17 N19 O8'
_chemical_formula_weight         555.44
_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      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                   9.7415(8)
_cell_length_b                   10.0524(7)
_cell_length_c                   12.6642(10)
_cell_angle_alpha                85.927(2)
_cell_angle_beta                 77.591(2)
_cell_angle_gamma                69.175(2)
_cell_volume                     1132.03(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3961
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.365
_cell_measurement_theta_min      2.285
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.745372
_exptl_absorpt_correction_T_min  0.626069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 23276 reflections, Rint = 0.0706
 (10805 with I > 3sig(I), Rint = 0.0531)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            4613
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.409
_diffrn_reflns_theta_min         2.285
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_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                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3167
_reflns_number_total             4613
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         4613
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.051
_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)+(0.0543P)²+0.2666P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1226
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N9-H9A = N9-H9B = N15-H15A = N15-H15B
 0.84 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N7(H7), N16(H16), C4(H4), C6(H6), C12(H12A), C10(H10)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.24047(17) 0.95785(16) 0.39192(13) 0.0230(4) Uani 1 1 d . . . . .
O4 O 0.7878(2) 0.57921(18) 1.14216(14) 0.0301(4) Uani 1 1 d . . . . .
O3 O 0.79893(19) 0.78928(17) 1.06538(14) 0.0274(4) Uani 1 1 d . . . . .
O1 O 0.46209(17) 0.79581(17) 0.42341(14) 0.0254(4) Uani 1 1 d . . . . .
O6 O 0.54094(19) 1.07307(18) 0.11852(15) 0.0295(4) Uani 1 1 d . . . . .
O7 O 0.6692(2) 1.2574(2) 0.08550(16) 0.0400(5) Uani 1 1 d . . . . .
N7 N 0.5222(2) 0.4248(2) 0.75645(16) 0.0229(5) Uani 1 1 d . . . . .
H7 H 0.441622 0.425021 0.804033 0.027 Uiso 1 1 calc R . . . .
N4 N 0.3026(2) 0.86496(19) 0.45456(16) 0.0207(4) Uani 1 1 d . . . . .
N8 N 0.6815(2) 0.21984(19) 0.83057(16) 0.0196(4) Uani 1 1 d . . . . .
N14 N 0.8166(2) 0.70022(19) 0.43519(16) 0.0189(4) Uani 1 1 d . . . . .
O5 O 0.5438(2) 0.9939(2) 0.28135(16) 0.0427(5) Uani 1 1 d . . . . .
N13 N 0.8491(2) 0.4720(2) 0.44032(16) 0.0216(5) Uani 1 1 d . . . . .
N16 N 0.7800(2) 0.7534(2) 0.61973(16) 0.0214(4) Uani 1 1 d . . . . .
H16 H 0.755863 0.845290 0.607042 0.026 Uiso 1 1 calc R . . . .
N11 N 0.9014(2) 0.2151(2) 0.73921(16) 0.0228(5) Uani 1 1 d . . . . .
N12 N 0.8276(2) 0.5242(2) 0.54334(17) 0.0195(4) Uani 1 1 d . . . . .
N15 N 0.7963(2) 0.8414(2) 0.40188(18) 0.0227(5) Uani 1 1 d D . . . .
N17 N 0.7915(2) 0.7016(2) 0.72135(16) 0.0203(4) Uani 1 1 d . . . . .
N3 N 0.5948(2) 1.0526(2) 0.20095(18) 0.0266(5) Uani 1 1 d . . . . .
N10 N 0.7896(2) 0.3301(2) 0.70260(16) 0.0212(4) Uani 1 1 d . . . . .
N5 N 0.5049(2) 0.6956(2) 0.50083(17) 0.0256(5) Uani 1 1 d . . . . .
N19 N 0.7931(2) 0.6507(2) 1.05694(17) 0.0245(5) Uani 1 1 d . . . . .
N2 N 0.7192(2) 1.0788(2) 0.21139(17) 0.0288(5) Uani 1 1 d . . . . .
O8 O 0.8873(2) 1.1670(2) 0.12826(19) 0.0499(6) Uani 1 1 d . . . . .
N6 N 0.5163(2) 0.5196(2) 0.67476(16) 0.0227(5) Uani 1 1 d . . . . .
N9 N 0.5609(2) 0.1913(2) 0.89979(19) 0.0256(5) Uani 1 1 d D . . . .
N1 N 0.7584(3) 1.1703(2) 0.13455(18) 0.0312(5) Uani 1 1 d . . . . .
N18 N 0.7960(2) 0.8501(2) 0.96506(17) 0.0268(5) Uani 1 1 d . . . . .
C5 C 0.6611(3) 0.3287(2) 0.76019(19) 0.0197(5) Uani 1 1 d . . . . .
C11 C 0.8061(2) 0.6617(2) 0.53965(19) 0.0180(5) Uani 1 1 d . . . . .
C4 C 0.3883(3) 0.6081(2) 0.6650(2) 0.0209(5) Uani 1 1 d . . . . .
H4 H 0.299730 0.611551 0.715655 0.025 Uiso 1 1 calc R . . . .
C6 C 0.8340(3) 0.1520(2) 0.8143(2) 0.0211(5) Uani 1 1 d . . . . .
H6 H 0.883229 0.070297 0.852576 0.025 Uiso 1 1 calc R . . . .
C3 C 0.3835(2) 0.7038(2) 0.5729(2) 0.0206(5) Uani 1 1 d . . . . .
C9 C 0.7916(2) 0.7557(2) 0.90072(19) 0.0203(5) Uani 1 1 d . . . . .
C2 C 0.2550(3) 0.8105(2) 0.54585(19) 0.0200(5) Uani 1 1 d . . . . .
C12 C 0.8421(2) 0.5806(2) 0.3775(2) 0.0213(5) Uani 1 1 d . . . . .
H12A H 0.853205 0.577678 0.301271 0.026 Uiso 1 1 calc R . . . .
C10 C 0.7843(3) 0.7940(3) 0.7888(2) 0.0226(5) Uani 1 1 d . . . . .
H10 H 0.774131 0.888342 0.765525 0.027 Uiso 1 1 calc R . . . .
C7 C 0.7898(3) 0.6287(3) 0.9571(2) 0.0248(6) Uani 1 1 d . . . . .
C1 C 0.0954(3) 0.8608(3) 0.5989(2) 0.0279(6) Uani 1 1 d . . . . .
H1A H 0.058094 0.964719 0.605905 0.042 Uiso 1 1 calc GR . . . .
H1B H 0.083629 0.818272 0.670849 0.042 Uiso 1 1 calc GR . . . .
H1C H 0.038053 0.832950 0.555329 0.042 Uiso 1 1 calc GR . . . .
C8 C 0.7804(4) 0.4949(3) 0.9227(2) 0.0477(8) Uani 1 1 d . . . . .
H8A H 0.792316 0.426116 0.981929 0.072 Uiso 1 1 calc GR . . . .
H8B H 0.860076 0.455490 0.859485 0.072 Uiso 1 1 calc GR . . . .
H8C H 0.682502 0.514616 0.904038 0.072 Uiso 1 1 calc GR . . . .
H12 H 0.813(3) 0.466(3) 0.604(2) 0.039(8) Uiso 1 1 d . . . . .
H15A H 0.717(2) 0.877(3) 0.376(2) 0.038(8) Uiso 1 1 d D . . . .
H15B H 0.874(2) 0.838(3) 0.3525(19) 0.038(9) Uiso 1 1 d D . . . .
H9A H 0.554(3) 0.115(2) 0.875(2) 0.036(8) Uiso 1 1 d D . . . .
H9B H 0.580(3) 0.181(3) 0.9643(17) 0.049(10) 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
O2 N4 1.252(2) . ?
O4 N19 1.255(3) . ?
O3 N19 1.427(3) . ?
O3 N18 1.372(3) . ?
O1 N4 1.436(2) . ?
O1 N5 1.374(2) . ?
O6 N3 1.239(3) . ?
O7 N1 1.233(3) . ?
N7 H7 0.8800 . ?
N7 N6 1.353(3) . ?
N7 C5 1.363(3) . ?
N4 C2 1.308(3) . ?
N8 N9 1.411(3) . ?
N8 C5 1.347(3) . ?
N8 C6 1.373(3) . ?
N14 N15 1.408(3) . ?
N14 C11 1.345(3) . ?
N14 C12 1.369(3) . ?
O5 N3 1.241(3) . ?
N13 N12 1.387(3) . ?
N13 C12 1.294(3) . ?
N16 H16 0.8800 . ?
N16 N17 1.366(3) . ?
N16 C11 1.341(3) . ?
N11 N10 1.408(3) . ?
N11 C6 1.296(3) . ?
N12 C11 1.322(3) . ?
N12 H12 0.95(3) . ?
N15 H15A 0.853(17) . ?
N15 H15B 0.862(17) . ?
N17 C10 1.280(3) . ?
N3 N2 1.363(3) . ?
N10 C5 1.311(3) . ?
N5 C3 1.309(3) . ?
N19 C7 1.308(3) . ?
N2 N1 1.379(3) . ?
O8 N1 1.229(3) . ?
N6 C4 1.274(3) . ?
N9 H9A 0.880(17) . ?
N9 H9B 0.866(18) . ?
N18 C9 1.312(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.456(3) . ?
C6 H6 0.9500 . ?
C3 C2 1.418(3) . ?
C9 C10 1.452(3) . ?
C9 C7 1.421(3) . ?
C2 C1 1.472(3) . ?
C12 H12A 0.9500 . ?
C10 H10 0.9500 . ?
C7 C8 1.482(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N18 O3 N19 107.11(16) . . ?
N5 O1 N4 106.91(16) . . ?
N6 N7 H7 122.2 . . ?
N6 N7 C5 115.58(19) . . ?
C5 N7 H7 122.2 . . ?
O2 N4 O1 116.84(18) . . ?
O2 N4 C2 134.5(2) . . ?
C2 N4 O1 108.61(17) . . ?
C5 N8 N9 122.62(18) . . ?
C5 N8 C6 105.06(19) . . ?
C6 N8 N9 132.29(19) . . ?
C11 N14 N15 122.4(2) . . ?
C11 N14 C12 106.48(18) . . ?
C12 N14 N15 131.1(2) . . ?
C12 N13 N12 104.72(19) . . ?
N17 N16 H16 120.6 . . ?
C11 N16 H16 120.6 . . ?
C11 N16 N17 118.75(19) . . ?
C6 N11 N10 107.25(18) . . ?
N13 N12 H12 118.9(18) . . ?
C11 N12 N13 110.30(19) . . ?
C11 N12 H12 129.8(18) . . ?
N14 N15 H15A 110.5(19) . . ?
N14 N15 H15B 106.6(18) . . ?
H15A N15 H15B 110(3) . . ?
C10 N17 N16 114.06(19) . . ?
O6 N3 O5 121.1(2) . . ?
O6 N3 N2 125.7(2) . . ?
O5 N3 N2 113.0(2) . . ?
C5 N10 N11 106.21(18) . . ?
C3 N5 O1 107.04(17) . . ?
O4 N19 O3 117.07(19) . . ?
O4 N19 C7 133.9(2) . . ?
C7 N19 O3 109.00(18) . . ?
N3 N2 N1 113.71(19) . . ?
C4 N6 N7 118.1(2) . . ?
N8 N9 H9A 107.8(19) . . ?
N8 N9 H9B 107(2) . . ?
H9A N9 H9B 113(3) . . ?
O7 N1 N2 123.7(2) . . ?
O8 N1 O7 123.0(2) . . ?
O8 N1 N2 112.9(2) . . ?
C9 N18 O3 106.89(19) . . ?
N8 C5 N7 121.9(2) . . ?
N10 C5 N7 127.0(2) . . ?
N10 C5 N8 111.12(19) . . ?
N16 C11 N14 122.8(2) . . ?
N12 C11 N14 107.2(2) . . ?
N12 C11 N16 130.1(2) . . ?
N6 C4 H4 121.4 . . ?
N6 C4 C3 117.2(2) . . ?
C3 C4 H4 121.4 . . ?
N8 C6 H6 124.8 . . ?
N11 C6 N8 110.3(2) . . ?
N11 C6 H6 124.8 . . ?
N5 C3 C4 121.4(2) . . ?
N5 C3 C2 111.4(2) . . ?
C2 C3 C4 127.2(2) . . ?
N18 C9 C10 118.5(2) . . ?
N18 C9 C7 111.3(2) . . ?
C7 C9 C10 130.1(2) . . ?
N4 C2 C3 106.0(2) . . ?
N4 C2 C1 121.3(2) . . ?
C3 C2 C1 132.6(2) . . ?
N14 C12 H12A 124.3 . . ?
N13 C12 N14 111.3(2) . . ?
N13 C12 H12A 124.3 . . ?
N17 C10 C9 120.5(2) . . ?
N17 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
N19 C7 C9 105.7(2) . . ?
N19 C7 C8 122.0(2) . . ?
C9 C7 C8 132.2(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
N16 H16 O2 0.88 1.99 2.833(2) 159.2 2_676 yes
N12 H12 N10 0.95(3) 1.83(3) 2.765(3) 170(3) . yes

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1909777'
loop_
_audit_author_name
_audit_author_address
'jie Tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-03-04 deposited with the CCDC.	2020-03-10 downloaded from the CCDC.
;
_audit_creation_date             2020-03-04
_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         'C5 H6 N8 O2, H2 O'
_chemical_formula_sum            'C5 H8 N8 O3'
_chemical_formula_weight         228.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.4819(13)
_cell_length_b                   5.2281(5)
_cell_length_c                   14.6301(19)
_cell_angle_alpha                90
_cell_angle_beta                 94.637(4)
_cell_angle_gamma                90
_cell_volume                     951.59(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1034
_cell_measurement_temperature    173
_cell_measurement_theta_max      24.78
_cell_measurement_theta_min      3.12
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   "'SADABS (Bruker, 2014)"
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0912
_diffrn_reflns_av_unetI/netI     0.0967
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4783
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.424
_diffrn_reflns_theta_min         3.122
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1046
_reflns_number_total             1736
_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_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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         0.304
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         1736
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1259
_refine_ls_R_factor_gt           0.0578
_refine_ls_restrained_S_all      1.022
_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)+(0.0601P)²+0.0777P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1398
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_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
C1 C 0.7888(3) 0.8287(6) 0.5060(3) 0.0214(8) Uani 1 1 d . . . . .
C2 C 0.6787(3) 0.8461(6) 0.5223(2) 0.0188(8) Uani 1 1 d . . . . .
C3 C 0.8771(3) 0.6559(6) 0.5386(3) 0.0321(10) Uani 1 1 d . . . . .
H3A H 0.870541 0.494615 0.504478 0.048 Uiso 1 1 calc GR . . . .
H3B H 0.873344 0.621968 0.604113 0.048 Uiso 1 1 calc GR . . . .
H3C H 0.946185 0.736367 0.528779 0.048 Uiso 1 1 calc GR . . . .
C4 C 0.6180(3) 0.6862(6) 0.5799(3) 0.0204(8) Uani 1 1 d . . . . .
H4 H 0.543806 0.717483 0.585401 0.025 Uiso 1 1 calc R . . . .
C5 C 0.6557(3) 0.1627(6) 0.7253(3) 0.0187(8) Uani 1 1 d . . . . .
N1 N 0.8056(2) 1.0160(5) 0.4478(2) 0.0223(7) Uani 1 1 d . . . . .
N2 N 0.6309(2) 1.0374(5) 0.4773(2) 0.0256(8) Uani 1 1 d . . . . .
N3 N 0.6666(2) 0.5002(5) 0.6235(2) 0.0210(7) Uani 1 1 d . . . . .
N4 N 0.6054(2) 0.3543(5) 0.6767(2) 0.0222(7) Uani 1 1 d . . . . .
N5 N 0.6065(2) -0.0054(5) 0.7760(2) 0.0216(7) Uani 1 1 d . . . . .
N6 N 0.6858(2) -0.1652(5) 0.8111(2) 0.0257(8) Uani 1 1 d . . . . .
N7 N 0.7780(2) -0.1033(5) 0.7844(2) 0.0272(8) Uani 1 1 d . . . . .
N8 N 0.7602(2) 0.1060(5) 0.7289(2) 0.0214(7) Uani 1 1 d . . . . .
O1 O 0.70750(18) 1.1542(4) 0.42877(18) 0.0274(7) Uani 1 1 d . . . . .
O2 O 0.88487(19) 1.0910(4) 0.4080(2) 0.0324(7) Uani 1 1 d . . . . .
O3 O 0.9758(2) 0.2012(6) 0.6996(2) 0.0365(8) Uani 1 1 d . . . . .
H4A H 0.537(3) 0.404(7) 0.686(3) 0.040(11) Uiso 1 1 d . . . . .
H8 H 0.816(3) 0.185(7) 0.705(3) 0.039(11) Uiso 1 1 d . . . . .
H3D H 1.018(3) 0.144(8) 0.670(3) 0.045(14) Uiso 1 1 d . . . . .
H3E H 1.004(5) 0.357(12) 0.730(5) 0.11(2) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.417(4) . ?
C1 C3 1.474(5) . ?
C1 N1 1.325(4) . ?
C2 C4 1.445(4) . ?
C2 N2 1.314(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4 0.9500 . ?
C4 N3 1.288(4) . ?
C5 N4 1.353(4) . ?
C5 N5 1.332(4) . ?
C5 N8 1.335(4) . ?
N1 O1 1.430(3) . ?
N1 O2 1.251(3) . ?
N2 O1 1.379(3) . ?
N3 N4 1.366(4) . ?
N4 H4A 0.91(4) . ?
N5 N6 1.364(4) . ?
N6 N7 1.286(4) . ?
N7 N8 1.370(4) . ?
N8 H8 0.90(4) . ?
O3 H3D 0.77(4) . ?
O3 H3E 0.98(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C3 134.0(3) . . ?
N1 C1 C2 105.5(3) . . ?
N1 C1 C3 120.5(3) . . ?
C1 C2 C4 128.5(3) . . ?
N2 C2 C1 111.9(3) . . ?
N2 C2 C4 119.6(3) . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4 120.7 . . ?
N3 C4 C2 118.5(3) . . ?
N3 C4 H4 120.7 . . ?
N5 C5 N4 124.5(3) . . ?
N5 C5 N8 108.9(3) . . ?
N8 C5 N4 126.6(3) . . ?
C1 N1 O1 108.8(2) . . ?
O2 N1 C1 134.6(3) . . ?
O2 N1 O1 116.6(3) . . ?
C2 N2 O1 106.8(2) . . ?
C4 N3 N4 116.2(3) . . ?
C5 N4 N3 117.1(3) . . ?
C5 N4 H4A 122(2) . . ?
N3 N4 H4A 120(2) . . ?
C5 N5 N6 105.1(3) . . ?
N7 N6 N5 111.8(3) . . ?
N6 N7 N8 106.0(3) . . ?
C5 N8 N7 108.2(3) . . ?
C5 N8 H8 131(2) . . ?
N7 N8 H8 120(2) . . ?
N2 O1 N1 107.1(2) . . ?
H3D O3 H3E 111(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4A N5 0.91(4) 1.98(4) 2.882(4) 172(4) 2_656 yes
N8 H8 O3 0.90(4) 2.01(4) 2.804(4) 146(3) . yes
O3 H3D O2 0.77(4) 2.12(4) 2.877(4) 167(4) 3_766 yes

_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_22019529_0m
_database_code_depnum_ccdc_archive 'CCDC 1918707'
loop_
_audit_author_name
_audit_author_address
'jie Tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-03-04 deposited with the CCDC.	2020-03-10 downloaded from the CCDC.
;
_audit_creation_date             2020-03-04
_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         '3(H2 O), C5 H5 N8 O2, H4 N'
_chemical_formula_sum            'C5 H15 N9 O5'
_chemical_formula_weight         281.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.765(3)
_cell_length_b                   7.205(3)
_cell_length_c                   23.573(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.770(15)
_cell_angle_gamma                90
_cell_volume                     1314.3(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3496
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.349
_cell_measurement_theta_min      2.995
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0992 before and 0.0556 after correction. The Ratio of minimum to maximum transmission is 0.8421. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11228
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.369
_diffrn_reflns_theta_min         2.702
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.940
_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                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2025
_reflns_number_total             2805
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2805
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.052
_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)+(0.0351P)²+0.5773P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.1005
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O3-H3B \\sim O3-H3A \\sim O2-H2B \\sim O2-H2A \\sim O1-H1A \\sim O1-H1B
 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N5(H5), C2(H2)
3.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.41364(18) 0.91367(19) 0.71899(6) 0.0248(3) Uani 1 1 d D . . . .
O3 O 0.78416(19) 0.66137(19) 0.64297(6) 0.0271(3) Uani 1 1 d D . . . .
O2 O 0.63107(19) 0.60564(19) 0.74764(6) 0.0260(3) Uani 1 1 d D . . . .
O4 O 0.85076(19) 0.76418(18) 0.33512(6) 0.0283(3) Uani 1 1 d . . . . .
O5 O 0.9496(2) 1.01468(19) 0.39083(6) 0.0359(4) Uani 1 1 d . . . . .
N9 N 0.0690(2) 0.7775(2) 0.72283(8) 0.0218(4) Uani 1 1 d . . . . .
N6 N 0.7031(2) 0.3932(2) 0.47820(7) 0.0205(4) Uani 1 1 d . . . . .
N2 N 0.5783(2) 0.0603(2) 0.63029(7) 0.0234(4) Uani 1 1 d . . . . .
N4 N 0.7027(2) 0.3094(2) 0.59785(7) 0.0227(4) Uani 1 1 d . . . . .
N8 N 0.8858(2) 0.8538(2) 0.39033(7) 0.0244(4) Uani 1 1 d . . . . .
N3 N 0.6655(2) 0.2137(2) 0.64543(7) 0.0250(4) Uani 1 1 d . . . . .
N1 N 0.5543(2) 0.0472(2) 0.57274(7) 0.0229(4) Uani 1 1 d . . . . .
N7 N 0.7786(2) 0.5900(2) 0.34448(7) 0.0273(4) Uani 1 1 d . . . . .
N5 N 0.6342(2) 0.2342(2) 0.49753(7) 0.0269(4) Uani 1 1 d . . . . .
H5 H 0.590406 0.150908 0.473115 0.032 Uiso 1 1 calc R . . . .
C1 C 0.6326(2) 0.2025(2) 0.55501(8) 0.0187(4) Uani 1 1 d . . . . .
C3 C 0.7712(2) 0.5753(2) 0.39995(8) 0.0193(4) Uani 1 1 d . . . . .
C4 C 0.8378(2) 0.7384(2) 0.42960(8) 0.0195(4) Uani 1 1 d . . . . .
C2 C 0.6996(2) 0.4077(3) 0.42358(8) 0.0231(4) Uani 1 1 d . . . . .
H2 H 0.651801 0.312028 0.399423 0.028 Uiso 1 1 calc R . . . .
C5 C 0.8547(3) 0.7895(3) 0.49094(8) 0.0265(5) Uani 1 1 d . . . . .
H5A H 0.959759 0.733211 0.509439 0.040 Uiso 1 1 calc GR . . . .
H5B H 0.753828 0.744070 0.509116 0.040 Uiso 1 1 calc GR . . . .
H5C H 0.861772 0.924781 0.494679 0.040 Uiso 1 1 calc GR . . . .
H9A H 0.181(3) 0.821(3) 0.7189(10) 0.044(7) Uiso 1 1 d . . . . .
H9B H 0.002(3) 0.747(3) 0.6890(11) 0.041(7) Uiso 1 1 d . . . . .
H9C H 0.074(3) 0.668(3) 0.7431(10) 0.039(6) Uiso 1 1 d . . . . .
H9D H 0.008(3) 0.868(3) 0.7412(10) 0.045(7) Uiso 1 1 d . . . . .
H3A H 0.742(3) 0.753(3) 0.6226(10) 0.057(8) Uiso 1 1 d D . . . .
H2A H 0.701(3) 0.646(4) 0.7761(9) 0.067(9) Uiso 1 1 d D . . . .
H1A H 0.483(3) 0.824(3) 0.7332(10) 0.052(8) Uiso 1 1 d D . . . .
H3B H 0.766(4) 0.559(3) 0.6226(11) 0.078(10) Uiso 1 1 d D . . . .
H2B H 0.688(3) 0.613(4) 0.7174(9) 0.063(9) Uiso 1 1 d D . . . .
H1B H 0.464(3) 0.951(3) 0.6884(8) 0.054(8) 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 H1A 0.889(16) . ?
O1 H1B 0.888(16) . ?
O3 H3A 0.864(16) . ?
O3 H3B 0.882(17) . ?
O2 H2A 0.875(17) . ?
O2 H2B 0.872(16) . ?
O4 N8 1.458(2) . ?
O4 N7 1.400(2) . ?
O5 N8 1.260(2) . ?
N9 H9A 0.94(3) . ?
N9 H9B 0.94(3) . ?
N9 H9C 0.92(3) . ?
N9 H9D 0.93(3) . ?
N6 N5 1.359(2) . ?
N6 C2 1.290(2) . ?
N2 N3 1.329(2) . ?
N2 N1 1.357(2) . ?
N4 N3 1.368(2) . ?
N4 C1 1.348(2) . ?
N8 C4 1.321(2) . ?
N1 C1 1.356(2) . ?
N7 C3 1.318(2) . ?
N5 H5 0.8800 . ?
N5 C1 1.375(2) . ?
C3 C4 1.441(3) . ?
C3 C2 1.459(3) . ?
C4 C5 1.487(3) . ?
C2 H2 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A O1 H1B 104(2) . . ?
H3A O3 H3B 107(3) . . ?
H2A O2 H2B 107(3) . . ?
N7 O4 N8 107.69(12) . . ?
H9A N9 H9B 117(2) . . ?
H9A N9 H9C 110(2) . . ?
H9A N9 H9D 109(2) . . ?
H9B N9 H9C 103.8(19) . . ?
H9B N9 H9D 107(2) . . ?
H9C N9 H9D 111(2) . . ?
C2 N6 N5 115.30(15) . . ?
N3 N2 N1 110.54(14) . . ?
C1 N4 N3 103.10(14) . . ?
O5 N8 O4 117.37(14) . . ?
O5 N8 C4 134.91(17) . . ?
C4 N8 O4 107.72(15) . . ?
N2 N3 N4 109.67(15) . . ?
C1 N1 N2 102.87(14) . . ?
C3 N7 O4 106.23(15) . . ?
N6 N5 H5 119.8 . . ?
N6 N5 C1 120.43(15) . . ?
C1 N5 H5 119.8 . . ?
N4 C1 N1 113.83(16) . . ?
N4 C1 N5 127.38(16) . . ?
N1 C1 N5 118.79(16) . . ?
N7 C3 C4 111.85(16) . . ?
N7 C3 C2 119.66(17) . . ?
C4 C3 C2 128.49(17) . . ?
N8 C4 C3 106.51(16) . . ?
N8 C4 C5 121.24(17) . . ?
C3 C4 C5 132.25(16) . . ?
N6 C2 C3 118.14(17) . . ?
N6 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

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
N9 H9A O1 0.94(3) 1.92(3) 2.859(3) 174(2) . yes
O1 H1A O2 0.889(16) 1.961(17) 2.836(2) 168(2) . yes
O3 H3B N4 0.882(17) 1.945(19) 2.802(2) 164(3) . yes
O2 H2B O3 0.872(16) 1.994(17) 2.855(2) 169(3) . yes
O1 H1B N2 0.888(16) 1.870(17) 2.751(2) 171(2) 1_565 yes

_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_ff
_database_code_depnum_ccdc_archive 'CCDC 1918708'
loop_
_audit_author_name
_audit_author_address
'jie Tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-03-04 deposited with the CCDC.	2020-03-10 downloaded from the CCDC.
;
_audit_creation_date             2020-03-04
_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 O4, C6 H9 N8 O2'
_chemical_formula_sum            'C6 H9 Cl N8 O6'
_chemical_formula_weight         324.66
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.9751(9)
_cell_length_b                   5.4951(3)
_cell_length_c                   14.4991(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.913(2)
_cell_angle_gamma                90
_cell_volume                     1235.46(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8285
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.870
_exptl_absorpt_coefficient_mu    0.358
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1184 before and 0.0509 after correction.
The Ratio of minimum to maximum transmission is 0.8659.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14034
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.517
_diffrn_reflns_theta_min         2.627
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_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                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2461
_reflns_number_total             2821
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2821
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.075
_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)+(0.0171P)²+1.2949P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0759
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C6-H6AA \\sim C6-H6BE \\sim C6-H6AC \\sim C6-H6BD \\sim C6-H6AB \\sim C6-H6BF
 with sigma of 0.02
3. Others
 Fixed Sof: H6BD(0.5) H6BE(0.5) H6BF(0.5) H6AA(0.5) H6AB(0.5) H6AC(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C1(H1)
4.b Idealised Me refined as rotating group:
 C6(H6BD,H6BE,H6BF)
;
_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
Cl00 Cl 0.38398(2) 0.02417(7) 0.31720(3) 0.01594(11) Uani 1 1 d . . . . .
O6 O -0.06148(7) 0.6515(2) 0.03167(8) 0.0175(3) Uani 1 1 d . . . . .
O5 O -0.02239(7) 0.3969(2) 0.15831(8) 0.0173(3) Uani 1 1 d . . . . .
O4 O 0.38299(8) -0.1161(2) 0.40180(8) 0.0235(3) Uani 1 1 d . . . . .
O1 O 0.43671(8) -0.0995(2) 0.26426(8) 0.0238(3) Uani 1 1 d . . . . .
O2 O 0.41933(8) 0.2604(2) 0.34517(9) 0.0272(3) Uani 1 1 d . . . . .
O3 O 0.29770(8) 0.0479(2) 0.26000(10) 0.0275(3) Uani 1 1 d . . . . .
N2 N 0.36907(8) 0.2640(3) 0.56474(9) 0.0144(3) Uani 1 1 d . . . . .
N6 N 0.19867(8) 0.4385(3) 0.36969(9) 0.0153(3) Uani 1 1 d . . . . .
N8 N -0.00462(8) 0.5962(3) 0.10397(9) 0.0141(3) Uani 1 1 d . . . . .
N5 N 0.27648(9) 0.4662(3) 0.43400(10) 0.0163(3) Uani 1 1 d . . . . .
N4 N 0.24023(9) 0.1291(3) 0.52008(10) 0.0175(3) Uani 1 1 d . . . . .
N3 N 0.28096(9) -0.0172(3) 0.59544(10) 0.0208(3) Uani 1 1 d . . . . .
N1 N 0.43951(9) 0.4167(3) 0.56446(11) 0.0172(3) Uani 1 1 d . . . . .
N7 N 0.04788(8) 0.3685(3) 0.23407(10) 0.0176(3) Uani 1 1 d . . . . .
C2 C 0.29327(10) 0.2966(3) 0.50193(11) 0.0143(3) Uani 1 1 d . . . . .
C4 C 0.10364(10) 0.5368(3) 0.22495(11) 0.0136(3) Uani 1 1 d . . . . .
C3 C 0.18633(10) 0.5664(3) 0.29460(11) 0.0152(3) Uani 1 1 d . . . . .
H3 H 0.228887 0.676611 0.284037 0.018 Uiso 1 1 calc R . . . .
C5 C 0.07262(10) 0.6813(3) 0.14294(11) 0.0142(3) Uani 1 1 d . . . . .
C1 C 0.35853(11) 0.0681(3) 0.62015(12) 0.0179(3) Uani 1 1 d . . . . .
H1 H 0.402691 0.003805 0.670178 0.021 Uiso 1 1 calc R . . . .
C6 C 0.10988(11) 0.8894(3) 0.10187(13) 0.0196(4) Uani 1 1 d D . . . .
H6BD H 0.089609 0.886068 0.032492 0.029 Uiso 0.5 1 calc DGR . P A 2
H6BE H 0.172948 0.878088 0.119605 0.029 Uiso 0.5 1 calc DGR . P A 2
H6BF H 0.091784 1.041880 0.126288 0.029 Uiso 0.5 1 calc DGR . P A 2
H5 H 0.3161(13) 0.551(4) 0.4233(13) 0.017(5) Uiso 1 1 d . . . . .
H4 H 0.1864(14) 0.117(4) 0.4938(14) 0.024(5) Uiso 1 1 d . . . . .
H1A H 0.4575(14) 0.481(4) 0.6215(16) 0.030(6) Uiso 1 1 d . . . . .
H1B H 0.4813(14) 0.328(4) 0.5550(15) 0.029(6) Uiso 1 1 d . . . . .
H6AA H 0.153(2) 0.970(8) 0.151(2) 0.028(11) Uiso 0.5 1 d D . P B 1
H6AB H 0.0651(18) 1.009(6) 0.079(3) 0.017(10) Uiso 0.5 1 d D . P C 1
H6AC H 0.129(3) 0.846(8) 0.045(2) 0.033(13) Uiso 0.5 1 d D . P D 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl00 O4 1.4519(13) . ?
Cl00 O1 1.4394(12) . ?
Cl00 O2 1.4349(13) . ?
Cl00 O3 1.4335(12) . ?
O6 N8 1.2484(16) . ?
O5 N8 1.4171(17) . ?
O5 N7 1.3777(16) . ?
N2 N1 1.4047(18) . ?
N2 C2 1.341(2) . ?
N2 C1 1.378(2) . ?
N6 N5 1.3712(18) . ?
N6 C3 1.271(2) . ?
N8 C5 1.314(2) . ?
N5 C2 1.336(2) . ?
N5 H5 0.83(2) . ?
N4 N3 1.3862(19) . ?
N4 C2 1.319(2) . ?
N4 H4 0.85(2) . ?
N3 C1 1.292(2) . ?
N1 H1A 0.88(2) . ?
N1 H1B 0.87(2) . ?
N7 C4 1.312(2) . ?
C4 C3 1.466(2) . ?
C4 C5 1.417(2) . ?
C3 H3 0.9500 . ?
C5 C6 1.479(2) . ?
C1 H1 0.9500 . ?
C6 H6BD 0.9800 . ?
C6 H6BE 0.9800 . ?
C6 H6BF 0.9800 . ?
C6 H6AA 0.968(16) . ?
C6 H6AB 0.968(15) . ?
C6 H6AC 0.971(16) . ?

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 Cl00 O4 109.05(8) . . ?
O2 Cl00 O4 108.96(8) . . ?
O2 Cl00 O1 109.70(8) . . ?
O3 Cl00 O4 109.43(8) . . ?
O3 Cl00 O1 109.82(8) . . ?
O3 Cl00 O2 109.86(8) . . ?
N7 O5 N8 107.28(11) . . ?
C2 N2 N1 120.77(13) . . ?
C2 N2 C1 106.47(13) . . ?
C1 N2 N1 132.76(13) . . ?
C3 N6 N5 116.73(14) . . ?
O6 N8 O5 116.90(12) . . ?
O6 N8 C5 133.88(14) . . ?
C5 N8 O5 109.21(12) . . ?
N6 N5 H5 122.8(13) . . ?
C2 N5 N6 114.36(14) . . ?
C2 N5 H5 120.3(13) . . ?
N3 N4 H4 122.4(14) . . ?
C2 N4 N3 111.06(13) . . ?
C2 N4 H4 126.3(14) . . ?
C1 N3 N4 104.20(14) . . ?
N2 N1 H1A 108.4(14) . . ?
N2 N1 H1B 108.2(15) . . ?
H1A N1 H1B 106.6(19) . . ?
C4 N7 O5 106.41(13) . . ?
N5 C2 N2 125.63(15) . . ?
N4 C2 N2 106.85(14) . . ?
N4 C2 N5 127.52(14) . . ?
N7 C4 C3 122.00(14) . . ?
N7 C4 C5 111.76(14) . . ?
C5 C4 C3 126.23(14) . . ?
N6 C3 C4 117.20(14) . . ?
N6 C3 H3 121.4 . . ?
C4 C3 H3 121.4 . . ?
N8 C5 C4 105.31(14) . . ?
N8 C5 C6 121.98(14) . . ?
C4 C5 C6 132.70(14) . . ?
N2 C1 H1 124.3 . . ?
N3 C1 N2 111.41(14) . . ?
N3 C1 H1 124.3 . . ?
C5 C6 H6BD 109.5 . . ?
C5 C6 H6BE 109.5 . . ?
C5 C6 H6BF 109.5 . . ?
C5 C6 H6AA 110(2) . . ?
C5 C6 H6AB 109(2) . . ?
C5 C6 H6AC 113(3) . . ?
H6BD C6 H6BE 109.5 . . ?
H6BD C6 H6BF 109.5 . . ?
H6BE C6 H6BF 109.5 . . ?
H6AA C6 H6AB 106(3) . . ?
H6AA C6 H6AC 115(3) . . ?
H6AB C6 H6AC 104(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4 O6 0.85(2) 1.95(2) 2.7752(17) 162(2) 2_545 yes

_olex2_submission_special_instructions 'No special instructions were received'
