# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2338599'
loop_
_audit_author_name
_audit_author_address
'Xiue Jiang'
;Northwestern Polytechnical University
China
;
_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_audit_creation_date             2023-12-11
_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         '2(Cl O4), C8 H10 N14 O4'
_chemical_formula_sum            'C8 H10 Cl2 N14 O12'
_chemical_formula_weight         565.20
_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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   6.1365(2)
_cell_length_b                   13.3475(4)
_cell_length_c                   12.6025(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.164(3)
_cell_angle_gamma                90
_cell_volume                     1031.50(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4357
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      75.7670
_cell_measurement_theta_min      6.6050
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.737
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             572
_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  0.0661
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10730
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         82.716
_diffrn_reflns_theta_min         4.828
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1667
_reflns_number_total             2132
_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         0.338
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2132
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.084
_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)+(0.0650P)²+0.4420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1455
_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:
 N003(H003)
2.b X=CH2 refined with riding coordinates:
 N005(H00A,H00B), N00E(H00C,H00D)
;
_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
Cl01 Cl -0.15763(11) 0.82309(5) 0.38339(5) 0.0560(3) Uani 1 1 d . . . . .
N002 N 0.5111(3) 0.68191(15) 0.57974(17) 0.0425(5) Uani 1 1 d . . . . .
N003 N 0.3256(3) 0.74200(16) 0.56716(18) 0.0478(5) Uani 1 1 d . . . . .
H003 H 0.207235 0.726068 0.532465 0.057 Uiso 1 1 calc R . . . .
O004 O 0.8473(3) 0.87875(17) 0.7754(2) 0.0742(7) Uani 1 1 d . . . . .
N005 N 0.8446(4) 0.68770(17) 0.6805(2) 0.0532(6) Uani 1 1 d . . . . .
H00A H 0.880303 0.628990 0.659025 0.064 Uiso 1 1 calc R . . . .
H00B H 0.930766 0.720272 0.723361 0.064 Uiso 1 1 calc R . . . .
N006 N 0.3054(4) 0.46315(17) 0.4618(2) 0.0517(6) Uani 1 1 d . . . . .
O007 O -0.1515(5) 0.88560(18) 0.29297(19) 0.0780(7) Uani 1 1 d . . . . .
N008 N 0.6649(4) 0.89425(18) 0.7362(2) 0.0578(6) Uani 1 1 d . . . . .
N009 N 0.3114(4) 0.55373(17) 0.5030(2) 0.0516(6) Uani 1 1 d . . . . .
O00A O -0.1760(5) 0.8818(2) 0.47730(19) 0.0800(8) Uani 1 1 d . . . . .
O00B O 0.5599(4) 0.97213(17) 0.7506(3) 0.0836(8) Uani 1 1 d . . . . .
C00C C 0.5055(4) 0.58578(19) 0.53879(19) 0.0407(5) Uani 1 1 d . . . . .
O00D O 0.0367(5) 0.7660(3) 0.3934(2) 0.1035(11) Uani 1 1 d . . . . .
N00E N 0.2261(4) 0.90386(19) 0.6137(2) 0.0632(7) Uani 1 1 d . . . . .
H00C H 0.106098 0.898530 0.576647 0.076 Uiso 1 1 calc R . . . .
H00D H 0.255606 0.958415 0.647626 0.076 Uiso 1 1 calc R . . . .
C00F C 0.6589(4) 0.72750(18) 0.6477(2) 0.0420(5) Uani 1 1 d . . . . .
C00G C 0.3633(4) 0.82918(19) 0.6186(2) 0.0467(6) Uani 1 1 d . . . . .
C00H C 0.5676(4) 0.82075(18) 0.6721(2) 0.0447(6) Uani 1 1 d . . . . .
O00I O -0.3383(6) 0.7591(3) 0.3696(3) 0.1208(13) 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
Cl01 O007 1.414(2) . ?
Cl01 O00A 1.428(2) . ?
Cl01 O00D 1.417(2) . ?
Cl01 O00I 1.405(3) . ?
N002 N003 1.397(3) . ?
N002 C00C 1.383(3) . ?
N002 C00F 1.367(3) . ?
N003 H003 0.8600 . ?
N003 C00G 1.348(3) . ?
O004 N008 1.224(3) . ?
N005 H00A 0.8600 . ?
N005 H00B 0.8600 . ?
N005 C00F 1.309(3) . ?
N006 N009 1.316(3) . ?
N006 C00C 1.332(3) 3_666 ?
N008 O00B 1.240(3) . ?
N008 C00H 1.391(3) . ?
N009 C00C 1.328(3) . ?
N00E H00C 0.8600 . ?
N00E H00D 0.8600 . ?
N00E C00G 1.305(3) . ?
C00F C00H 1.404(4) . ?
C00G C00H 1.405(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
O007 Cl01 O00A 110.46(16) . . ?
O007 Cl01 O00D 109.97(19) . . ?
O00D Cl01 O00A 108.29(15) . . ?
O00I Cl01 O007 107.69(19) . . ?
O00I Cl01 O00A 110.4(2) . . ?
O00I Cl01 O00D 110.0(2) . . ?
C00C N002 N003 118.79(19) . . ?
C00F N002 N003 109.53(19) . . ?
C00F N002 C00C 130.8(2) . . ?
N002 N003 H003 125.8 . . ?
C00G N003 N002 108.46(19) . . ?
C00G N003 H003 125.8 . . ?
H00A N005 H00B 120.0 . . ?
C00F N005 H00A 120.0 . . ?
C00F N005 H00B 120.0 . . ?
N009 N006 C00C 116.2(2) . 3_666 ?
O004 N008 O00B 123.7(2) . . ?
O004 N008 C00H 118.8(2) . . ?
O00B N008 C00H 117.5(2) . . ?
N006 N009 C00C 116.2(2) . . ?
N006 C00C N002 116.6(2) 3_666 . ?
N009 C00C N002 115.8(2) . . ?
N009 C00C N006 127.6(2) . 3_666 ?
H00C N00E H00D 120.0 . . ?
C00G N00E H00C 120.0 . . ?
C00G N00E H00D 120.0 . . ?
N002 C00F C00H 105.7(2) . . ?
N005 C00F N002 124.4(2) . . ?
N005 C00F C00H 129.8(2) . . ?
N003 C00G C00H 107.2(2) . . ?
N00E C00G N003 122.6(2) . . ?
N00E C00G C00H 130.3(3) . . ?
N008 C00H C00F 125.9(2) . . ?
N008 C00H C00G 125.3(2) . . ?
C00F C00H C00G 108.8(2) . . ?

_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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2338600'
loop_
_audit_author_name
_audit_author_address
'Xiue Jiang'
;Northwestern Polytechnical University
China
;
_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_audit_creation_date             2024-01-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H14 N18 O6, 2(H2 O), 2(Cl O4)'
_chemical_formula_sum            'C12 H18 Cl2 N18 O16'
_chemical_formula_weight         741.34
_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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   14.8517(3)
_cell_length_b                   15.5923(3)
_cell_length_c                   12.3844(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.337(2)
_cell_angle_gamma                90
_cell_volume                     2652.69(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15000
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      76.2520
_cell_measurement_theta_min      3.2130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.249
_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            'metallic light white'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.856
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1512
_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  0.0334
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25495
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.632
_diffrn_reflns_theta_min         3.217
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4256
_reflns_number_total             5341
_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, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         5341
_refine_ls_number_restraints     80
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0645
_refine_ls_restrained_S_all      1.079
_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)+(0.1361P)²+1.2327P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1945
_refine_ls_wR_factor_ref         0.2095
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 H9A-N9
 2 with sigma of 0.02
 H9B-O4
 2 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O1 \\sim O1A: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
O2 \\sim O2A: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
O3A \\sim O3: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
O10A \\sim O10: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(O1A) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O2) \\sim Ueq, Uanis(O2A) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O3A) \\sim Ueq, Uanis(O3) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O10A) \\sim Ueq, Uanis(O10) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O4) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Sof(O1A)=1-FVAR(1)
 Sof(O1)=FVAR(1)
 Sof(O2A)=1-FVAR(2)
 Sof(O2)=FVAR(2)
 Sof(O3A)=1-FVAR(3)
 Sof(O3)=FVAR(3)
 Sof(O10A)=1-FVAR(4)
 Sof(O10)=FVAR(4)
5.a Free rotating group:
 O9(H9A,H9B), O10(H10A,H10B)
5.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N15(H15)
5.c X=CH2 refined with riding coordinates:
 N11(H11A,H11B), N5(H5A,H5B), N2(H2A,H2B), N12(H12A,H12B), N18(H18A,H18B),
 N16(H16A,H16B)
;
_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
O2AA O 0.69758(18) 0.36058(18) 1.0497(2) 0.0680(6) Uani 1 1 d . . . . .
N10 N 0.48815(18) 0.48631(16) 0.7792(2) 0.0501(6) Uani 1 1 d . . . . .
O4AA O 0.08420(19) 0.77509(19) 0.1907(2) 0.0703(7) Uani 1 1 d . . . . .
O6AA O 0.2350(2) 0.74134(19) 0.2326(2) 0.0717(7) Uani 1 1 d . . . . .
N6 N 0.20477(18) 0.55032(17) 0.6722(2) 0.0515(6) Uani 1 1 d . . . . .
N8 N 0.35496(18) 0.55733(16) 0.6424(2) 0.0488(5) Uani 1 1 d . . . . .
N4 N 0.21708(19) 0.63305(17) 0.5262(2) 0.0508(6) Uani 1 1 d . . . . .
N7 N 0.34352(18) 0.47678(17) 0.7996(2) 0.0506(6) Uani 1 1 d . . . . .
N13 N 0.7129(2) 0.39335(19) 0.9679(3) 0.0586(7) Uani 1 1 d . . . . .
N14 N 0.19846(19) 0.46533(19) 0.8228(2) 0.0558(6) Uani 1 1 d . . . . .
N9 N 0.5472(2) 0.50680(18) 0.7186(3) 0.0567(6) Uani 1 1 d D . . . .
N11 N 0.5033(2) 0.40373(18) 0.9475(2) 0.0549(6) Uani 1 1 d . . . . .
H11A H 0.4428 0.4111 0.9352 0.066 Uiso 1 1 calc R . . . .
H11B H 0.5397 0.3741 1.0064 0.066 Uiso 1 1 calc R . . . .
O3AA O 0.79266(19) 0.3942(2) 0.9599(3) 0.0834(8) Uani 1 1 d . . . . .
N3 N 0.1169(2) 0.64800(19) 0.4924(2) 0.0549(6) Uani 1 1 d . . . . .
H3 H 0.0815 0.6314 0.5295 0.066 Uiso 1 1 calc R . . . .
N1 N 0.1619(2) 0.74096(18) 0.2555(2) 0.0567(6) Uani 1 1 d . . . . .
O7AA O -0.0718(2) 0.4464(2) 0.8324(3) 0.0868(9) Uani 1 1 d . . . . .
N5 N 0.3366(2) 0.6587(2) 0.4477(2) 0.0608(7) Uani 1 1 d . . . . .
H5A H 0.3806 0.6341 0.5062 0.073 Uiso 1 1 calc R . . . .
H5B H 0.3513 0.6796 0.3922 0.073 Uiso 1 1 calc R . . . .
N15 N 0.2506(2) 0.4168(2) 0.9253(2) 0.0597(7) Uani 1 1 d . . . . .
H15 H 0.3113 0.4036 0.9530 0.072 Uiso 1 1 calc R . . . .
N2 N -0.0043(2) 0.7195(2) 0.3420(3) 0.0645(7) Uani 1 1 d . . . . .
H2A H -0.0457 0.7085 0.3733 0.077 Uiso 1 1 calc R . . . .
H2B H -0.0220 0.7480 0.2778 0.077 Uiso 1 1 calc R . . . .
C2 C 0.5397(2) 0.43751(18) 0.8766(3) 0.0487(6) Uani 1 1 d . . . . .
C4 C 0.3905(2) 0.50765(18) 0.7371(3) 0.0477(6) Uani 1 1 d . . . . .
C6 C 0.2620(2) 0.57667(19) 0.6183(2) 0.0483(6) Uani 1 1 d . . . . .
N12 N 0.7130(2) 0.4909(2) 0.7517(3) 0.0672(8) Uani 1 1 d . . . . .
H12A H 0.7049 0.5187 0.6887 0.081 Uiso 1 1 calc R . . . .
H12B H 0.7697 0.4716 0.7943 0.081 Uiso 1 1 calc R . . . .
N17 N 0.0031(2) 0.4189(2) 0.9101(3) 0.0702(8) Uani 1 1 d . . . . .
C7 C 0.2475(2) 0.66419(19) 0.4429(2) 0.0505(7) Uani 1 1 d . . . . .
C9 C 0.0859(2) 0.6928(2) 0.3920(3) 0.0522(7) Uani 1 1 d . . . . .
C3 C 0.6346(2) 0.4332(2) 0.8799(3) 0.0517(7) Uani 1 1 d . . . . .
C8 C 0.1651(2) 0.7016(2) 0.3568(3) 0.0529(7) Uani 1 1 d . . . . .
O8AA O 0.0031(3) 0.3813(3) 0.9977(3) 0.0988(11) Uani 1 1 d . . . . .
N18 N 0.0378(2) 0.5118(2) 0.7142(3) 0.0748(9) Uani 1 1 d . . . . .
H18A H 0.0547 0.5355 0.6622 0.090 Uiso 1 1 calc R . . . .
H18B H -0.0219 0.5138 0.7078 0.090 Uiso 1 1 calc R . . . .
C5 C 0.2501(2) 0.49899(19) 0.7616(3) 0.0494(6) Uani 1 1 d . . . . .
C1 C 0.6385(2) 0.4777(2) 0.7829(3) 0.0539(7) Uani 1 1 d . . . . .
C11 C 0.0912(2) 0.4291(2) 0.8957(3) 0.0576(7) Uani 1 1 d . . . . .
N16 N 0.2054(3) 0.3525(2) 1.0671(3) 0.0786(9) Uani 1 1 d . . . . .
H16A H 0.2641 0.3360 1.1056 0.094 Uiso 1 1 calc R . . . .
H16B H 0.1603 0.3406 1.0924 0.094 Uiso 1 1 calc R . . . .
C12 C 0.1022(2) 0.4730(2) 0.8024(3) 0.0562(7) Uani 1 1 d . . . . .
C10 C 0.1841(3) 0.3967(2) 0.9682(3) 0.0588(8) Uani 1 1 d . . . . .
O9 O 0.5793(4) 0.6226(3) 0.5755(4) 0.1297(16) Uani 1 1 d . . . . .
H9A H 0.5652 0.5680 0.5835 0.195 Uiso 1 1 d DG . . . .
H9B H 0.5748 0.6365 0.5074 0.195 Uiso 1 1 d DG . . . .
Cl1 Cl 0.50173(7) 0.76165(6) 0.30103(8) 0.0644(3) Uani 1 1 d . . . . .
Cl2 Cl -0.16397(6) 0.62601(6) 0.53866(8) 0.0709(3) Uani 1 1 d . . . . .
O8 O -0.1725(2) 0.5462(2) 0.5911(3) 0.0878(9) Uani 1 1 d . . . . .
O5 O -0.0863(3) 0.6200(2) 0.4999(3) 0.0946(9) Uani 1 1 d . . . . .
O6 O -0.1428(3) 0.6942(3) 0.6197(4) 0.1093(12) Uani 1 1 d . . . . .
O2 O 0.4396(9) 0.7590(4) 0.1757(4) 0.087(3) Uani 0.71(2) 1 d . U P A 1
O7 O -0.2529(3) 0.6399(3) 0.4428(3) 0.1087(12) Uani 1 1 d . . . . .
O1 O 0.4337(4) 0.7897(5) 0.3494(4) 0.114(2) Uani 0.823(15) 1 d . U P A 1
O3 O 0.5769(4) 0.8221(4) 0.3422(6) 0.131(3) Uani 0.799(14) 1 d . U P A 1
O1A O 0.484(2) 0.8311(15) 0.3437(18) 0.098(9) Uani 0.177(15) 1 d . U P A 2
O2A O 0.4911(18) 0.7814(12) 0.1908(15) 0.084(5) Uani 0.29(2) 1 d . U P A 2
O3A O 0.588(2) 0.759(2) 0.277(3) 0.159(13) Uani 0.201(14) 1 d . U P A 2
O10 O 0.6960(6) 0.7584(4) 0.6967(7) 0.117(3) Uani 0.670(14) 1 d . U P B 1
H10A H 0.7346 0.7895 0.6776 0.175 Uiso 1 1 d G . . . .
H10B H 0.6702 0.7250 0.6387 0.175 Uiso 1 1 d G . . . .
O10A O 0.7859(16) 0.7817(13) 0.7720(17) 0.146(7) Uani 0.330(14) 1 d . U P B 2
O4 O 0.5248(4) 0.6782(2) 0.3363(3) 0.1407(19) Uani 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2AA N13 1.230(4) . ?
N10 N9 1.390(4) . ?
N10 C2 1.386(4) . ?
N10 C4 1.382(4) . ?
O4AA N1 1.247(4) . ?
O6AA N1 1.223(4) . ?
N6 C6 1.330(4) . ?
N6 C5 1.324(4) . ?
N8 C4 1.335(4) . ?
N8 C6 1.331(4) . ?
N4 N3 1.403(4) . ?
N4 C6 1.393(4) . ?
N4 C7 1.363(4) . ?
N7 C4 1.315(4) . ?
N7 C5 1.331(4) . ?
N13 O3AA 1.226(4) . ?
N13 C3 1.401(4) . ?
N14 N15 1.427(4) . ?
N14 C5 1.370(4) . ?
N14 C12 1.359(4) . ?
N9 C1 1.362(4) . ?
N11 H11A 0.8600 . ?
N11 H11B 0.8600 . ?
N11 C2 1.304(4) . ?
N3 H3 0.8600 . ?
N3 C9 1.346(4) . ?
N1 C8 1.381(4) . ?
O7AA N17 1.238(4) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N5 C7 1.304(4) . ?
N15 H15 0.8600 . ?
N15 C10 1.324(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C9 1.312(4) . ?
C2 C3 1.397(4) . ?
N12 H12A 0.8600 . ?
N12 H12B 0.8600 . ?
N12 C1 1.320(4) . ?
N17 O8AA 1.234(4) . ?
N17 C11 1.396(4) . ?
C7 C8 1.408(4) . ?
C9 C8 1.408(5) . ?
C3 C1 1.407(5) . ?
N18 H18A 0.8600 . ?
N18 H18B 0.8600 . ?
N18 C12 1.296(5) . ?
C11 C12 1.405(5) . ?
C11 C10 1.422(5) . ?
N16 H16A 0.8600 . ?
N16 H16B 0.8600 . ?
N16 C10 1.335(5) . ?
O9 H9A 0.8911 . ?
O9 H9B 0.8497 . ?
Cl1 O2 1.474(5) . ?
Cl1 O1 1.425(4) . ?
Cl1 O3 1.400(5) . ?
Cl1 O1A 1.28(2) . ?
Cl1 O2A 1.349(13) . ?
Cl1 O3A 1.42(3) . ?
Cl1 O4 1.375(4) . ?
Cl2 O8 1.432(3) . ?
Cl2 O5 1.411(4) . ?
Cl2 O6 1.413(4) . ?
Cl2 O7 1.417(3) . ?
O2A O3A 1.47(4) . ?
O10 H10A 0.8504 . ?
O10 H10B 0.8506 . ?
O10A H10A 1.1335 . ?

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 N10 N9 110.0(2) . . ?
C4 N10 N9 121.9(2) . . ?
C4 N10 C2 127.9(3) . . ?
C5 N6 C6 112.8(3) . . ?
C6 N8 C4 111.0(2) . . ?
C6 N4 N3 118.2(2) . . ?
C7 N4 N3 109.5(2) . . ?
C7 N4 C6 130.6(3) . . ?
C4 N7 C5 114.3(3) . . ?
O2AA N13 C3 117.8(3) . . ?
O3AA N13 O2AA 123.9(3) . . ?
O3AA N13 C3 118.3(3) . . ?
C5 N14 N15 117.8(2) . . ?
C12 N14 N15 112.8(3) . . ?
C12 N14 C5 129.3(3) . . ?
C1 N9 N10 107.5(3) . . ?
H11A N11 H11B 120.0 . . ?
C2 N11 H11A 120.0 . . ?
C2 N11 H11B 120.0 . . ?
N4 N3 H3 125.9 . . ?
C9 N3 N4 108.3(3) . . ?
C9 N3 H3 125.9 . . ?
O4AA N1 C8 118.7(3) . . ?
O6AA N1 O4AA 122.3(3) . . ?
O6AA N1 C8 119.0(3) . . ?
H5A N5 H5B 120.0 . . ?
C7 N5 H5A 120.0 . . ?
C7 N5 H5B 120.0 . . ?
N14 N15 H15 127.8 . . ?
C10 N15 N14 104.3(3) . . ?
C10 N15 H15 127.8 . . ?
H2A N2 H2B 120.0 . . ?
C9 N2 H2A 120.0 . . ?
C9 N2 H2B 120.0 . . ?
N10 C2 C3 105.6(3) . . ?
N11 C2 N10 125.1(3) . . ?
N11 C2 C3 129.3(3) . . ?
N8 C4 N10 118.6(3) . . ?
N7 C4 N10 113.9(3) . . ?
N7 C4 N8 127.5(3) . . ?
N6 C6 N8 128.6(3) . . ?
N6 C6 N4 114.0(3) . . ?
N8 C6 N4 117.4(3) . . ?
H12A N12 H12B 120.0 . . ?
C1 N12 H12A 120.0 . . ?
C1 N12 H12B 120.0 . . ?
O7AA N17 C11 118.1(3) . . ?
O8AA N17 O7AA 123.2(3) . . ?
O8AA N17 C11 118.6(3) . . ?
N4 C7 C8 106.1(3) . . ?
N5 C7 N4 124.4(3) . . ?
N5 C7 C8 129.6(3) . . ?
N3 C9 C8 107.6(3) . . ?
N2 C9 N3 122.1(3) . . ?
N2 C9 C8 130.3(3) . . ?
N13 C3 C1 126.3(3) . . ?
C2 C3 N13 125.0(3) . . ?
C2 C3 C1 108.6(3) . . ?
N1 C8 C7 126.3(3) . . ?
N1 C8 C9 125.4(3) . . ?
C7 C8 C9 108.3(3) . . ?
H18A N18 H18B 120.0 . . ?
C12 N18 H18A 120.0 . . ?
C12 N18 H18B 120.0 . . ?
N6 C5 N7 125.7(3) . . ?
N6 C5 N14 118.7(3) . . ?
N7 C5 N14 115.6(3) . . ?
N9 C1 C3 108.0(3) . . ?
N12 C1 N9 122.4(3) . . ?
N12 C1 C3 129.6(3) . . ?
N17 C11 C12 124.6(3) . . ?
N17 C11 C10 127.7(3) . . ?
C12 C11 C10 107.7(3) . . ?
H16A N16 H16B 120.0 . . ?
C10 N16 H16A 120.0 . . ?
C10 N16 H16B 120.0 . . ?
N14 C12 C11 104.3(3) . . ?
N18 C12 N14 125.8(3) . . ?
N18 C12 C11 129.8(3) . . ?
N15 C10 C11 110.8(3) . . ?
N15 C10 N16 122.5(3) . . ?
N16 C10 C11 126.7(3) . . ?
H9A O9 H9B 115.0 . . ?
O1 Cl1 O2 101.0(5) . . ?
O3 Cl1 O2 119.8(5) . . ?
O3 Cl1 O1 103.6(4) . . ?
O1A Cl1 O2A 105.2(12) . . ?
O1A Cl1 O3A 117(2) . . ?
O1A Cl1 O4 137.5(11) . . ?
O2A Cl1 O3A 63.9(16) . . ?
O2A Cl1 O4 117.2(7) . . ?
O4 Cl1 O2 106.8(3) . . ?
O4 Cl1 O1 106.7(4) . . ?
O4 Cl1 O3 117.0(4) . . ?
O4 Cl1 O3A 84.7(14) . . ?
O5 Cl2 O8 108.7(2) . . ?
O5 Cl2 O6 107.6(2) . . ?
O5 Cl2 O7 110.3(3) . . ?
O6 Cl2 O8 111.5(3) . . ?
O6 Cl2 O7 111.4(3) . . ?
O7 Cl2 O8 107.4(2) . . ?
Cl1 O2A O3A 60.4(15) . . ?
Cl1 O3A O2A 55.7(14) . . ?
H10A O10 H10B 104.4 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
