# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_y
_audit_block_doi                 10.5517/ccdc.csd.cc2hyn48
_database_code_depnum_ccdc_archive 'CCDC 2322400'
loop_
_audit_author_name
_audit_author_address
LHY
;northwestern polytechnical university 
China
;
_audit_update_record             
;
2023-12-29 deposited with the CCDC.	2024-02-07 downloaded from the CCDC.
;
_audit_creation_date             2023-11-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'N O3, C5 H5 N8 O4'
_chemical_formula_sum            'C5 H5 N9 O7'
_chemical_formula_weight         303.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.7501(6)
_cell_length_b                   8.8976(5)
_cell_length_c                   24.5696(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2131.5(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4373
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      30.4030
_cell_measurement_theta_min      2.6500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.890
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            13334
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.752
_diffrn_reflns_theta_min         2.667
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                1999
_reflns_number_total             2806
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2806
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.046
_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)+(0.0540P)²+0.4920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1107
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
2.a X=CH2 refined with riding coordinates:
 N8(H8A,H8B), N7(H7A,H7B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
O5 O 0.16706(12) 0.67632(14) 0.48073(5) 0.0230(3) Uani 1 1 d . . . . .
O6 O -0.03689(11) 0.61544(14) 0.45316(5) 0.0223(3) Uani 1 1 d . . . . .
O7 O 0.13922(12) 0.49528(14) 0.42197(5) 0.0244(3) Uani 1 1 d . . . . .
O3 O 0.44974(13) 0.09561(16) 0.22035(5) 0.0274(3) Uani 1 1 d . . . . .
O4 O 0.55665(15) -0.06419(15) 0.27195(5) 0.0316(3) Uani 1 1 d . . . . .
N4 N 0.41476(15) 0.44595(15) 0.40174(6) 0.0174(3) Uani 1 1 d . . . . .
N2 N 0.60067(13) 0.33459(16) 0.35732(5) 0.0171(3) Uani 1 1 d . . . . .
N3 N 0.64331(14) 0.52239(16) 0.42146(6) 0.0186(3) Uani 1 1 d . . . . .
N9 N 0.08985(14) 0.59501(16) 0.45237(6) 0.0186(3) Uani 1 1 d . . . . .
N1 N 0.63727(14) 0.22720(16) 0.31960(6) 0.0202(3) Uani 1 1 d . . . . .
N8 N 0.46031(14) 0.64226(16) 0.46005(6) 0.0203(3) Uani 1 1 d . . . . .
H8A H 0.516317 0.700167 0.477124 0.024 Uiso 1 1 calc R . . . .
H8B H 0.373315 0.653077 0.464302 0.024 Uiso 1 1 calc R . . . .
N6 N 0.50815(15) 0.05898(17) 0.26226(6) 0.0217(3) Uani 1 1 d . . . . .
N7 N 0.82317(14) 0.39438(17) 0.38290(6) 0.0216(3) Uani 1 1 d . . . . .
H7A H 0.881079 0.445632 0.401674 0.026 Uiso 1 1 calc R . . . .
H7B H 0.851721 0.326461 0.360718 0.026 Uiso 1 1 calc R . . . .
C2 C 0.69216(16) 0.41963(18) 0.38805(7) 0.0176(3) Uani 1 1 d . . . . .
C4 C 0.46314(16) 0.34553(18) 0.36529(6) 0.0166(3) Uani 1 1 d . . . . .
C3 C 0.50732(16) 0.53800(19) 0.42770(7) 0.0176(3) Uani 1 1 d . . . . .
C5 C 0.40554(16) 0.23932(18) 0.33134(7) 0.0179(3) Uani 1 1 d . . . . .
C1 C 0.51797(17) 0.17351(19) 0.30474(7) 0.0188(3) Uani 1 1 d . . . . .
N5 N 0.26671(14) 0.19468(16) 0.32824(6) 0.0191(3) Uani 1 1 d . . . . .
O1 O 0.24044(12) 0.08139(14) 0.30144(5) 0.0246(3) Uani 1 1 d . . . . .
O2 O 0.18233(12) 0.26921(15) 0.35392(5) 0.0258(3) Uani 1 1 d . . . . .
H4 H 0.328(2) 0.455(2) 0.4073(8) 0.026(5) 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
O5 N9 1.2553(18) . ?
O6 N9 1.2491(17) . ?
O7 N9 1.2559(18) . ?
O3 N6 1.2212(19) . ?
O4 N6 1.2170(19) . ?
N4 C4 1.350(2) . ?
N4 C3 1.376(2) . ?
N4 H4 0.86(2) . ?
N2 N1 1.378(2) . ?
N2 C2 1.392(2) . ?
N2 C4 1.359(2) . ?
N3 C2 1.318(2) . ?
N3 C3 1.342(2) . ?
N1 C1 1.309(2) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N8 C3 1.305(2) . ?
N6 C1 1.462(2) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N7 C2 1.303(2) . ?
C4 C5 1.380(2) . ?
C5 C1 1.404(2) . ?
C5 N5 1.413(2) . ?
N5 O1 1.2311(19) . ?
N5 O2 1.2307(18) . ?

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
C4 N4 C3 118.20(14) . . ?
C4 N4 H4 120.6(14) . . ?
C3 N4 H4 121.2(14) . . ?
N1 N2 C2 125.14(13) . . ?
C4 N2 N1 113.71(13) . . ?
C4 N2 C2 121.02(14) . . ?
C2 N3 C3 120.01(14) . . ?
O5 N9 O7 120.50(13) . . ?
O6 N9 O5 120.05(14) . . ?
O6 N9 O7 119.43(14) . . ?
C1 N1 N2 102.15(13) . . ?
H8A N8 H8B 120.0 . . ?
C3 N8 H8A 120.0 . . ?
C3 N8 H8B 120.0 . . ?
O3 N6 C1 116.53(14) . . ?
O4 N6 O3 125.90(15) . . ?
O4 N6 C1 117.56(14) . . ?
H7A N7 H7B 120.0 . . ?
C2 N7 H7A 120.0 . . ?
C2 N7 H7B 120.0 . . ?
N3 C2 N2 118.90(14) . . ?
N7 C2 N2 118.79(15) . . ?
N7 C2 N3 122.30(15) . . ?
N4 C4 N2 119.19(14) . . ?
N4 C4 C5 135.40(15) . . ?
N2 C4 C5 105.40(14) . . ?
N3 C3 N4 122.24(15) . . ?
N8 C3 N4 118.39(15) . . ?
N8 C3 N3 119.36(15) . . ?
C4 C5 C1 104.43(14) . . ?
C4 C5 N5 127.96(15) . . ?
C1 C5 N5 127.28(15) . . ?
N1 C1 N6 120.77(14) . . ?
N1 C1 C5 114.31(15) . . ?
C5 C1 N6 124.88(14) . . ?
O1 N5 C5 117.28(14) . . ?
O2 N5 C5 117.48(14) . . ?
O2 N5 O1 125.19(14) . . ?

_shelx_SHELXL_version_number     2017/1
_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 2322401'
loop_
_audit_author_name
_audit_author_address
'Lv Hongyu'
;northwestern polytechnical university
China
;
_audit_update_record             
;
2023-12-29 deposited with the CCDC.	2024-02-07 downloaded from the CCDC.
;
_audit_creation_date             2020-09-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl O4, C5 H5 N8 O4'
_chemical_formula_sum            'C5 H5 Cl N8 O8'
_chemical_formula_weight         340.62
_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                   7.2532(4)
_cell_length_b                   12.1486(8)
_cell_length_c                   13.3337(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.280(2)
_cell_angle_gamma                90
_cell_volume                     1138.61(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5502
_cell_measurement_temperature    181
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.406
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1221 before and 0.0663 after correction. The Ratio of minimum to maximum transmission is 0.8620. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.987
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10654
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_min         2.301
_diffrn_ambient_temperature      181.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                2166
_reflns_number_total             2577
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2577
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.040
_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)+(0.0399P)²+0.8123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0982
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2)
2.b X=CH2 refined with riding coordinates:
 N4(H4A,H4B), N6(H6A,H6B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.06598(6) 0.65298(4) 0.12588(3) 0.02073(14) Uani 1 1 d . . . . .
O1 O -0.40478(18) 0.67324(12) -0.30738(10) 0.0266(3) Uani 1 1 d . . . . .
N2 N 0.1786(2) 0.65293(13) -0.11760(11) 0.0190(3) Uani 1 1 d . . . . .
H2 H 0.118507 0.694196 -0.081641 0.023 Uiso 1 1 calc R . . . .
O3 O 0.0944(2) 0.74587(12) 0.06343(11) 0.0292(3) Uani 1 1 d . . . . .
N4 N 0.4451(2) 0.43754(14) -0.26304(13) 0.0251(4) Uani 1 1 d . . . . .
H4A H 0.563526 0.416547 -0.237549 0.030 Uiso 1 1 calc R . . . .
H4B H 0.377820 0.408473 -0.321026 0.030 Uiso 1 1 calc R . . . .
N5 N 0.0727(2) 0.50123(13) -0.35061(12) 0.0202(3) Uani 1 1 d . . . . .
N6 N 0.4640(2) 0.68513(14) 0.00006(12) 0.0249(4) Uani 1 1 d . . . . .
H6A H 0.586488 0.672933 0.024579 0.030 Uiso 1 1 calc R . . . .
H6B H 0.405164 0.733108 0.030651 0.030 Uiso 1 1 calc R . . . .
N7 N 0.1821(2) 0.54202(13) -0.25896(11) 0.0185(3) Uani 1 1 d . . . . .
N8 N -0.2471(2) 0.67607(13) -0.24701(12) 0.0199(3) Uani 1 1 d . . . . .
N9 N 0.4602(2) 0.55931(13) -0.12775(12) 0.0211(3) Uani 1 1 d . . . . .
O10 O -0.3066(2) 0.60903(13) -0.50010(11) 0.0330(4) Uani 1 1 d . . . . .
O11 O -0.20802(19) 0.72811(12) -0.16490(10) 0.0274(3) Uani 1 1 d . . . . .
O12 O 0.1313(2) 0.55453(13) 0.08796(12) 0.0360(4) Uani 1 1 d . . . . .
C13 C 0.0856(2) 0.60910(15) -0.20869(13) 0.0175(4) Uani 1 1 d . . . . .
O14 O -0.2807(2) 0.43291(13) -0.47461(12) 0.0384(4) Uani 1 1 d . . . . .
C15 C 0.3691(2) 0.51194(16) -0.21476(14) 0.0201(4) Uani 1 1 d . . . . .
N16 N -0.2400(2) 0.52767(14) -0.45031(12) 0.0229(4) Uani 1 1 d . . . . .
O17 O 0.1736(2) 0.67062(13) 0.23074(11) 0.0355(4) Uani 1 1 d . . . . .
O18 O -0.1321(2) 0.64513(14) 0.12467(12) 0.0355(4) Uani 1 1 d . . . . .
C19 C -0.0973(2) 0.61511(15) -0.27081(13) 0.0176(4) Uani 1 1 d . . . . .
C20 C 0.3693(2) 0.63181(16) -0.08209(13) 0.0195(4) Uani 1 1 d . . . . .
C21 C -0.0924(2) 0.54726(16) -0.35593(14) 0.0190(4) 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
Cl1 O3 1.4470(14) . ?
Cl1 O12 1.4243(15) . ?
Cl1 O17 1.4394(15) . ?
Cl1 O18 1.4358(14) . ?
O1 N8 1.226(2) . ?
N2 C13 1.345(2) . ?
N2 C20 1.371(2) . ?
N4 C15 1.308(2) . ?
N5 N7 1.375(2) . ?
N5 C21 1.307(2) . ?
N6 C20 1.312(2) . ?
N7 C13 1.355(2) . ?
N7 C15 1.388(2) . ?
N8 O11 1.235(2) . ?
N8 C19 1.415(2) . ?
N9 C15 1.317(2) . ?
N9 C20 1.334(2) . ?
O10 N16 1.222(2) . ?
C13 C19 1.381(2) . ?
O14 N16 1.213(2) . ?
N16 C21 1.457(2) . ?
C19 C21 1.410(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 Cl1 O3 110.09(9) . . ?
O12 Cl1 O17 108.76(10) . . ?
O12 Cl1 O18 111.08(10) . . ?
O17 Cl1 O3 108.84(9) . . ?
O18 Cl1 O3 109.23(9) . . ?
O18 Cl1 O17 108.79(10) . . ?
C13 N2 C20 118.45(16) . . ?
C21 N5 N7 102.37(15) . . ?
N5 N7 C15 124.89(15) . . ?
C13 N7 N5 113.64(14) . . ?
C13 N7 C15 121.23(15) . . ?
O1 N8 O11 124.72(16) . . ?
O1 N8 C19 118.82(15) . . ?
O11 N8 C19 116.46(15) . . ?
C15 N9 C20 119.57(16) . . ?
N2 C13 N7 118.64(15) . . ?
N2 C13 C19 135.57(17) . . ?
N7 C13 C19 105.78(15) . . ?
N4 C15 N7 117.35(16) . . ?
N4 C15 N9 123.68(17) . . ?
N9 C15 N7 118.96(17) . . ?
O10 N16 C21 116.43(16) . . ?
O14 N16 O10 125.81(16) . . ?
O14 N16 C21 117.69(16) . . ?
C13 C19 N8 124.77(16) . . ?
C13 C19 C21 103.94(15) . . ?
C21 C19 N8 131.28(16) . . ?
N6 C20 N2 118.17(17) . . ?
N6 C20 N9 119.42(16) . . ?
N9 C20 N2 122.41(16) . . ?
N5 C21 N16 116.42(16) . . ?
N5 C21 C19 114.25(15) . . ?
C19 C21 N16 129.20(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
