# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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 2390031'
loop_
_audit_author_name
_audit_author_address
'Xiue Jiang'
;Northwestern Polytechnical University
China
;
_audit_update_record             
;
2024-10-10 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;
_audit_creation_date             2024-09-14
_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         'C7 H7 N9 O5, H2 O, C3 H7 N O'
_chemical_formula_sum            'C11 H16 N9 O7'
_chemical_formula_weight         386.33
_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'
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'

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

_cell_length_a                   16.6318(4)
_cell_length_b                   14.9763(3)
_cell_length_c                   6.9855(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.907(2)
_cell_angle_gamma                90.00
_cell_volume                     1733.59(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7453
_cell_measurement_temperature    298
_cell_measurement_theta_max      76.3300
_cell_measurement_theta_min      2.6400
_exptl_absorpt_coefficient_mu    1.081
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            19223
_diffrn_reflns_theta_full        76.70
_diffrn_reflns_theta_max         76.70
_diffrn_reflns_theta_min         2.67
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2868
_reflns_number_total             3592
_reflns_threshold_expression     >2sigma(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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3592
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0780P)²+0.1090P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1375
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O002(H00M,H00N)
2.b Aromatic/amide H refined with riding coordinates:
 N006(H006), C00P(H00P)
2.c X=CH2 refined with riding coordinates:
 N009(H00A,H00B), N00D(H00C,H00D), N00E(H00E,H00F)
2.d Idealised Me refined as rotating group:
 C00Q(H00G,H00H,H00I), C00R(H00J,H00K,H00L)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O001 O 0.56573(7) 0.41296(7) 0.75231(16) 0.0461(3) Uani 1 d . . .
O002 O 0.38124(8) 0.46552(8) 0.52827(18) 0.0496(3) Uani 1 d . . .
H00M H 0.3310 0.4598 0.4963 0.074 Uiso 1 d . . G
H00N H 0.4022 0.4988 0.4474 0.074 Uiso 1 d . . G
O003 O 0.67834(8) 0.15650(8) 0.8637(2) 0.0588(3) Uani 1 d . . .
N004 N 0.45312(7) 0.22521(8) 0.62893(17) 0.0357(3) Uani 1 d . . .
O005 O 0.69901(8) 0.29833(8) 0.8918(2) 0.0617(4) Uani 1 d . . .
N006 N 0.46484(8) 0.31724(8) 0.64354(19) 0.0399(3) Uani 1 d . . .
H006 H 0.4292 0.3567 0.6066 0.048 Uiso 1 calc . . R
N007 N 0.37505(8) 0.10227(8) 0.55299(18) 0.0389(3) Uani 1 d . . .
N008 N 0.32606(8) 0.25050(8) 0.48647(18) 0.0379(3) Uani 1 d . . .
N009 N 0.52898(9) 0.09502(8) 0.71485(19) 0.0419(3) Uani 1 d . . .
H00A H 0.4894 0.0613 0.6732 0.050 Uiso 1 calc . . R
H00B H 0.5733 0.0716 0.7634 0.050 Uiso 1 calc . . R
N00A N 0.65506(8) 0.23462(8) 0.84293(19) 0.0409(3) Uani 1 d . . .
O00B O 0.22100(9) 0.46413(10) 0.4053(3) 0.0717(4) Uani 1 d . . .
O00C O 0.15623(9) 0.00586(10) 0.3209(2) 0.0693(4) Uani 1 d . . .
N00D N 0.30155(9) -0.02146(9) 0.4818(2) 0.0485(4) Uani 1 d . . .
H00C H 0.3420 -0.0516 0.5320 0.058 Uiso 1 calc . . R
H00D H 0.2587 -0.0486 0.4353 0.058 Uiso 1 calc . . R
N00E N 0.20033(9) 0.27785(10) 0.3500(2) 0.0499(4) Uani 1 d . . .
H00E H 0.2114 0.3338 0.3610 0.060 Uiso 1 calc . . R
H00F H 0.1538 0.2610 0.2998 0.060 Uiso 1 calc . . R
O00F O 0.11181(9) 0.13812(11) 0.2617(3) 0.0813(5) Uani 1 d . . .
N00G N 0.16719(9) 0.08742(11) 0.3242(2) 0.0537(4) Uani 1 d . . .
C00H C 0.37952(9) 0.19023(9) 0.55134(19) 0.0341(3) Uani 1 d . . .
C00I C 0.52166(9) 0.18255(9) 0.70424(19) 0.0344(3) Uani 1 d . . .
C00J C 0.57697(9) 0.25028(9) 0.7632(2) 0.0349(3) Uani 1 d . . .
C00K C 0.25508(10) 0.21759(10) 0.4102(2) 0.0385(3) Uani 1 d . . .
C00L C 0.53990(10) 0.33604(9) 0.7237(2) 0.0366(3) Uani 1 d . . .
C00M C 0.30518(10) 0.06613(10) 0.4762(2) 0.0384(3) Uani 1 d . . .
C00N C 0.24167(10) 0.12326(10) 0.3985(2) 0.0407(3) Uani 1 d . . .
N00O N 0.12258(12) 0.55860(14) 0.3021(3) 0.0775(5) Uani 1 d . . .
C00P C 0.19672(13) 0.53863(14) 0.3668(3) 0.0633(5) Uani 1 d . . .
H00P H 0.2335 0.5853 0.3843 0.076 Uiso 1 calc . . R
C00Q C 0.06317(17) 0.4867(2) 0.2705(5) 0.1030(10) Uani 1 d . . .
H00G H 0.0675 0.4606 0.1463 0.154 Uiso 1 calc . . GR
H00H H 0.0099 0.5105 0.2767 0.154 Uiso 1 calc . . GR
H00I H 0.0732 0.4419 0.3678 0.154 Uiso 1 calc . . GR
C00R C 0.0995(3) 0.6478(3) 0.2442(9) 0.182(3) Uani 1 d . . .
H00J H 0.1446 0.6873 0.2703 0.273 Uiso 1 calc . . GR
H00K H 0.0555 0.6672 0.3145 0.273 Uiso 1 calc . . GR
H00L H 0.0830 0.6485 0.1091 0.273 Uiso 1 calc . . GR


_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
O001 C00L 1.2396(18) . ?
O002 H00M 0.8503 . ?
O002 H00N 0.8500 . ?
O003 N00A 1.2370(17) . ?
N004 N006 1.3945(16) . ?
N004 C00H 1.3975(19) . ?
N004 C00I 1.3718(19) . ?
O005 N00A 1.2323(18) . ?
N006 H006 0.8600 . ?
N006 C00L 1.353(2) . ?
N007 C00H 1.3196(18) . ?
N007 C00M 1.351(2) . ?
N008 C00H 1.320(2) . ?
N008 C00K 1.346(2) . ?
N009 H00A 0.8600 . ?
N009 H00B 0.8600 . ?
N009 C00I 1.3179(18) . ?
N00A C00J 1.389(2) . ?
O00B C00P 1.209(2) . ?
O00C N00G 1.235(2) . ?
N00D H00C 0.8600 . ?
N00D H00D 0.8600 . ?
N00D C00M 1.314(2) . ?
N00E H00E 0.8600 . ?
N00E H00F 0.8600 . ?
N00E C00K 1.325(2) . ?
O00F N00G 1.244(2) . ?
N00G C00N 1.408(2) . ?
C00I C00J 1.407(2) . ?
C00J C00L 1.441(2) . ?
C00K C00N 1.431(2) . ?
C00M C00N 1.430(2) . ?
N00O C00P 1.311(3) . ?
N00O C00Q 1.465(4) . ?
N00O C00R 1.438(4) . ?
C00P H00P 0.9300 . ?
C00Q H00G 0.9600 . ?
C00Q H00H 0.9600 . ?
C00Q H00I 0.9600 . ?
C00R H00J 0.9600 . ?
C00R H00K 0.9600 . ?
C00R H00L 0.9600 . ?

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
H00M O002 H00N 109.5 . . ?
N006 N004 C00H 120.74(12) . . ?
C00I N004 N006 109.02(12) . . ?
C00I N004 C00H 130.22(12) . . ?
N004 N006 H006 124.6 . . ?
C00L N006 N004 110.74(12) . . ?
C00L N006 H006 124.6 . . ?
C00H N007 C00M 116.35(13) . . ?
C00H N008 C00K 115.33(13) . . ?
H00A N009 H00B 120.0 . . ?
C00I N009 H00A 120.0 . . ?
C00I N009 H00B 120.0 . . ?
O003 N00A C00J 118.64(13) . . ?
O005 N00A O003 121.85(15) . . ?
O005 N00A C00J 119.51(13) . . ?
H00C N00D H00D 120.0 . . ?
C00M N00D H00C 120.0 . . ?
C00M N00D H00D 120.0 . . ?
H00E N00E H00F 120.0 . . ?
C00K N00E H00E 120.0 . . ?
C00K N00E H00F 120.0 . . ?
O00C N00G O00F 119.58(16) . . ?
O00C N00G C00N 120.52(15) . . ?
O00F N00G C00N 119.91(16) . . ?
N007 C00H N004 114.77(13) . . ?
N007 C00H N008 130.46(14) . . ?
N008 C00H N004 114.77(13) . . ?
N004 C00I C00J 106.10(12) . . ?
N009 C00I N004 123.68(14) . . ?
N009 C00I C00J 130.22(14) . . ?
N00A C00J C00I 124.14(13) . . ?
N00A C00J C00L 126.69(13) . . ?
C00I C00J C00L 109.17(13) . . ?
N008 C00K C00N 120.72(14) . . ?
N00E C00K N008 115.58(14) . . ?
N00E C00K C00N 123.70(15) . . ?
O001 C00L N006 123.69(14) . . ?
O001 C00L C00J 131.35(15) . . ?
N006 C00L C00J 104.96(12) . . ?
N007 C00M C00N 119.57(14) . . ?
N00D C00M N007 115.37(14) . . ?
N00D C00M C00N 125.06(15) . . ?
N00G C00N C00K 121.67(15) . . ?
N00G C00N C00M 120.66(14) . . ?
C00M C00N C00K 117.56(14) . . ?
C00P N00O C00Q 119.1(2) . . ?
C00P N00O C00R 122.0(3) . . ?
C00R N00O C00Q 118.7(3) . . ?
O00B C00P N00O 125.0(2) . . ?
O00B C00P H00P 117.5 . . ?
N00O C00P H00P 117.5 . . ?
N00O C00Q H00G 109.5 . . ?
N00O C00Q H00H 109.5 . . ?
N00O C00Q H00I 109.5 . . ?
H00G C00Q H00H 109.5 . . ?
H00G C00Q H00I 109.5 . . ?
H00H C00Q H00I 109.5 . . ?
N00O C00R H00J 109.5 . . ?
N00O C00R H00K 109.5 . . ?
N00O C00R H00L 109.5 . . ?
H00J C00R H00K 109.5 . . ?
H00J C00R H00L 109.5 . . ?
H00K C00R H00L 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2390033'
loop_
_audit_author_name
_audit_author_address
'Xiue Jiang'
;Northwestern Polytechnical University
China
;
_audit_update_record             
;
2024-10-10 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;
_audit_creation_date             2024-04-24
_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         'Cl O4, C6 H7 N8 O4'
_chemical_formula_sum            'C6 H7 Cl N8 O8'
_chemical_formula_weight         354.65
_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'

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

_cell_length_a                   8.0018(2)
_cell_length_b                   17.4218(4)
_cell_length_c                   9.2060(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.350(3)
_cell_angle_gamma                90.00
_cell_volume                     1203.27(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4410
_cell_measurement_temperature    298
_cell_measurement_theta_max      76.3980
_cell_measurement_theta_min      5.6900
_exptl_absorpt_coefficient_mu    3.524
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_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    1.958
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11146
_diffrn_reflns_theta_full        77.21
_diffrn_reflns_theta_max         77.21
_diffrn_reflns_theta_min         5.08
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.947
_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                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1937
_reflns_number_total             2410
_reflns_threshold_expression     >2sigma(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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2410
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0920P)²+0.1470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1364
_refine_ls_wR_factor_ref         0.1452
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
2.a X=CH2 refined with riding coordinates:
 N00G(H00A,H00C), N00H(H00E,H00F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl01 Cl -0.15591(8) 0.38418(4) 0.77564(8) 0.0343(2) Uani 1 d . . .
O002 O 0.2978(3) 0.19303(12) 0.5636(3) 0.0459(5) Uani 1 d . . .
O003 O 0.1327(3) 0.42844(13) 0.5066(3) 0.0441(5) Uani 1 d . . .
O004 O -0.1040(3) 0.30711(13) 0.8236(3) 0.0517(6) Uani 1 d . . .
O005 O 0.1300(3) 0.27971(13) 0.6136(3) 0.0489(6) Uani 1 d . . .
N006 N 0.6918(3) 0.35661(13) 0.2765(3) 0.0336(5) Uani 1 d . . .
O007 O -0.0586(3) 0.43553(15) 0.8971(3) 0.0577(7) Uani 1 d . . .
O008 O 0.6329(3) 0.57361(13) 0.1195(3) 0.0586(7) Uani 1 d . . .
O009 O -0.3423(3) 0.39139(14) 0.7502(3) 0.0538(6) Uani 1 d . . .
N00A N 0.4669(3) 0.37967(13) 0.3746(3) 0.0326(5) Uani 1 d . . .
N00B N 0.5542(3) 0.47737(14) 0.2511(3) 0.0367(6) Uani 1 d . . .
N00C N 0.3490(3) 0.43357(14) 0.3993(3) 0.0360(5) Uani 1 d . . .
N00D N 0.7804(3) 0.45972(14) 0.1541(3) 0.0399(6) Uani 1 d . . .
N00E N 0.2427(3) 0.25960(13) 0.5565(3) 0.0346(5) Uani 1 d . . .
O00F O -0.1232(3) 0.40199(14) 0.6370(3) 0.0549(6) Uani 1 d . . .
N00G N 0.9123(3) 0.34139(14) 0.1745(3) 0.0396(6) Uani 1 d . . .
H00A H 0.9797 0.3589 0.1269 0.048 Uiso 1 calc . . R
H00C H 0.9220 0.2943 0.2045 0.048 Uiso 1 calc . . R
N00H N 0.5334(3) 0.24511(14) 0.4082(3) 0.0409(6) Uani 1 d . . .
H00E H 0.6134 0.2487 0.3659 0.049 Uiso 1 calc . . R
H00F H 0.5114 0.2014 0.4413 0.049 Uiso 1 calc . . R
C00I C 0.4447(3) 0.30648(16) 0.4226(3) 0.0311(6) Uani 1 d . . .
C00J C 0.5767(3) 0.40418(15) 0.2984(3) 0.0312(6) Uani 1 d . . .
C00K C 0.3083(3) 0.31560(16) 0.4840(3) 0.0321(6) Uani 1 d . . .
C00L C 0.2580(3) 0.39369(16) 0.4657(3) 0.0338(6) Uani 1 d . . .
C00M C 0.7961(3) 0.38596(16) 0.2009(3) 0.0328(6) Uani 1 d . . .
C00N C 0.6544(4) 0.50932(18) 0.1700(4) 0.0395(7) Uani 1 d . . .
H003 H 0.095(6) 0.390(3) 0.552(6) 0.083(15) Uiso 1 d . . .
H00B H 0.478(4) 0.5060(19) 0.260(4) 0.042(9) Uiso 1 d . . .
H00D H 0.844(6) 0.480(3) 0.111(6) 0.093(16) Uiso 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 O004 1.429(2) . ?
Cl01 O007 1.432(2) . ?
Cl01 O009 1.433(2) . ?
Cl01 O00F 1.423(2) . ?
O002 N00E 1.234(3) . ?
O003 C00L 1.333(3) . ?
O003 H003 0.90(5) . ?
O005 N00E 1.242(3) . ?
N006 C00J 1.306(3) . ?
N006 C00M 1.359(3) . ?
O008 C00N 1.202(4) . ?
N00A N00C 1.404(3) . ?
N00A C00I 1.381(3) . ?
N00A C00J 1.370(3) . ?
N00B C00J 1.339(4) . ?
N00B C00N 1.388(3) . ?
N00B H00B 0.82(3) . ?
N00C C00L 1.303(3) . ?
N00D C00M 1.347(4) . ?
N00D C00N 1.374(4) . ?
N00D H00D 0.82(5) . ?
N00E C00K 1.384(3) . ?
N00G H00A 0.8600 . ?
N00G H00C 0.8600 . ?
N00G C00M 1.298(3) . ?
N00H H00E 0.8600 . ?
N00H H00F 0.8600 . ?
N00H C00I 1.315(3) . ?
C00I C00K 1.402(3) . ?
C00K C00L 1.412(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
O004 Cl01 O007 108.96(16) . . ?
O004 Cl01 O009 107.89(13) . . ?
O007 Cl01 O009 108.99(15) . . ?
O00F Cl01 O004 110.93(14) . . ?
O00F Cl01 O007 110.13(15) . . ?
O00F Cl01 O009 109.87(15) . . ?
C00L O003 H003 102(3) . . ?
C00J N006 C00M 115.6(2) . . ?
C00I N00A N00C 113.4(2) . . ?
C00J N00A N00C 117.5(2) . . ?
C00J N00A C00I 128.9(2) . . ?
C00J N00B C00N 121.3(2) . . ?
C00J N00B H00B 125(2) . . ?
C00N N00B H00B 114(2) . . ?
C00L N00C N00A 103.6(2) . . ?
C00M N00D C00N 123.8(2) . . ?
C00M N00D H00D 124(3) . . ?
C00N N00D H00D 112(3) . . ?
O002 N00E O005 122.8(2) . . ?
O002 N00E C00K 120.0(2) . . ?
O005 N00E C00K 117.3(2) . . ?
H00A N00G H00C 120.0 . . ?
C00M N00G H00A 120.0 . . ?
C00M N00G H00C 120.0 . . ?
H00E N00H H00F 120.0 . . ?
C00I N00H H00E 120.0 . . ?
C00I N00H H00F 120.0 . . ?
N00A C00I C00K 103.2(2) . . ?
N00H C00I N00A 125.8(2) . . ?
N00H C00I C00K 131.0(3) . . ?
N006 C00J N00A 119.6(2) . . ?
N006 C00J N00B 125.2(2) . . ?
N00B C00J N00A 115.2(2) . . ?
N00E C00K C00I 126.4(2) . . ?
N00E C00K C00L 126.6(2) . . ?
C00I C00K C00L 106.9(2) . . ?
O003 C00L C00K 128.0(2) . . ?
N00C C00L O003 119.3(2) . . ?
N00C C00L C00K 112.8(2) . . ?
N00D C00M N006 121.1(2) . . ?
N00G C00M N006 118.6(3) . . ?
N00G C00M N00D 120.3(2) . . ?
O008 C00N N00B 123.4(3) . . ?
O008 C00N N00D 123.8(2) . . ?
N00D C00N N00B 112.8(3) . . ?

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

data_a
_database_code_depnum_ccdc_archive 'CCDC 2390032'
loop_
_audit_author_name
_audit_author_address
'Xiue Jiang'
;Northwestern Polytechnical University
China
;
_audit_update_record             
;
2024-10-10 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;
_audit_creation_date             2024-06-02
_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         '4(Cl H O4), 6(C8 H6 N12 O6), 10(H2 O)'
_chemical_formula_sum            'C48 H60 Cl4 N72 O62'
_chemical_formula_weight         2779.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.5731(5)
_cell_length_b                   16.0518(8)
_cell_length_c                   16.8857(13)
_cell_angle_alpha                118.314(2)
_cell_angle_beta                 108.221(2)
_cell_angle_gamma                90.012(2)
_cell_volume                     2358.3(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3626
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.46
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1288 before and 0.0643 after correction. The Ratio of minimum to maximum transmission is 0.7463. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.957
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_av_unetI/netI     0.0844
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24520
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.123
_diffrn_reflns_theta_max         25.123
_diffrn_reflns_theta_min         2.061
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3891
_reflns_number_total             8358
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.164
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     903
_refine_ls_number_reflns         8358
_refine_ls_number_restraints     341
_refine_ls_R_factor_all          0.1720
_refine_ls_R_factor_gt           0.0872
_refine_ls_restrained_S_all      1.024
_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)+(0.1031P)²+7.8452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2110
_refine_ls_wR_factor_ref         0.2735
_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
 O8-H8
 0.88 with sigma of 0.02
 O22-H22
 0.88 with sigma of 0.02
 Cl00-H22
 2 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O10 \\sim O10A: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
O7A \\sim O7: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
O9 \\sim O9A: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
O8A \\sim O8: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(C18) \\sim Ueq, Uanis(C24) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O29) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O31) \\sim Ueq, Uanis(O32) \\sim Ueq, Uanis(O33) \\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(O7A) \\sim Ueq, Uanis(O7) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O9) \\sim Ueq, Uanis(O9A) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O8) \\sim Ueq, Uanis(O10) \\sim Ueq, Uanis(O7) \\sim Ueq, Uanis(O9) \\sim
Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O8) \\sim Ueq, Uanis(O8A) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O27) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
5. Others
 Fixed Sof: O10(0.8) O7(0.8) O8(0.8) O9(0.8) O30(0.5) H30A(0.5) H30B(0.5)
 O31(0.5) H31A(0.5) H31B(0.5) O32(0.5) H32C(0.5) H32D(0.5) O33(0.5) H33A(0.5)
 H33B(0.5) O10A(0.2) O7A(0.2) O9A(0.2) O8A(0.2)
6.a Riding coordinates:
 O27(H27C,H27D), O28(H28A,H28B), O29(H29A,H29B), O30(H30A,H30B), O31(H31A,
 H31B), O33(H33A,H33B)
6.b Free rotating group:
 O32(H32C,H32D)
6.c Aromatic/amide H refined with riding coordinates:
 N21(H21), N25(H25), N33(H33), N10(H10), N16(H16), N4(H4)
6.d X=CH2 refined with riding coordinates:
 N20(H20A,H20B), N27(H27A,H27B), N13(H13A,H13B), N2(H2A,H2B), N11(H11A,H11B),
 N32(H32A,H32B)
;
_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 0.08825(19) 0.33520(13) 0.66884(13) 0.0422(5) Uani 1 1 d D U . . .
Cl1 Cl 1.4234(2) 0.66856(12) 0.33608(14) 0.0453(5) Uani 1 1 d . U . . .
O5 O 0.6166(5) 0.9796(3) 0.2632(3) 0.0455(13) Uani 1 1 d . U . . .
O26 O 0.3561(5) 0.1498(3) 0.2366(3) 0.0437(12) Uani 1 1 d . U . . .
O16 O 0.6955(5) 0.7684(3) 0.9127(3) 0.0450(13) Uani 1 1 d . U . . .
O14 O 0.5108(5) 0.7166(4) 0.9795(4) 0.0468(13) Uani 1 1 d . U . . .
O15 O 0.3596(5) 0.5881(4) 0.8747(3) 0.0465(13) Uani 1 1 d . U . . .
N3 N 0.3693(5) 0.6838(3) 0.0967(4) 0.0280(12) Uani 1 1 d . U . . .
O4 O 0.3371(5) 0.9155(3) 0.1460(4) 0.0458(13) Uani 1 1 d . U . . .
O6 O 0.7225(5) 0.8736(3) 0.2885(4) 0.0477(13) Uani 1 1 d . U . . .
O25 O 0.1553(5) 0.2614(3) 0.2846(4) 0.0473(13) Uani 1 1 d . U . . .
O3 O 0.1581(5) 0.0895(3) -0.1461(4) 0.0489(14) Uani 1 1 d . U . . .
N23 N 1.0839(5) 0.9404(4) 0.4642(4) 0.0329(13) Uani 1 1 d . U . . .
O18 O 1.3646(5) 0.7070(4) 0.5798(5) 0.0600(16) Uani 1 1 d . U . . .
O24 O 0.1217(5) 0.2848(3) 0.4136(4) 0.0465(13) Uani 1 1 d . U . . .
O12 O 1.0072(5) 0.2899(4) 0.0258(4) 0.0503(14) Uani 1 1 d . U . . .
O2 O -0.2272(6) 0.1309(4) -0.2896(4) 0.0606(16) Uani 1 1 d . U . . .
O17 O 1.3430(5) 0.7359(4) 0.7136(4) 0.0584(16) Uani 1 1 d . U . . .
N22 N 1.1150(5) 0.9037(4) 0.5855(4) 0.0306(13) Uani 1 1 d . U . . .
O13 O 0.8167(5) 0.2361(4) 0.0865(3) 0.0501(14) Uani 1 1 d . U . . .
N8 N 0.1150(5) 0.4788(4) -0.0581(4) 0.0330(13) Uani 1 1 d . U . . .
O11 O 1.1497(6) 0.4236(4) 0.1320(4) 0.0586(16) Uani 1 1 d . U . . .
N34 N 0.3856(5) 0.0980(4) 0.4157(4) 0.0319(13) Uani 1 1 d . U . . .
O19 O 1.1558(5) 0.8574(4) 0.7708(4) 0.0519(14) Uani 1 1 d . U . . .
N17 N 0.8987(5) 0.4236(4) 0.4313(4) 0.0324(13) Uani 1 1 d . U . . .
N18 N 0.9063(5) 0.4660(4) 0.5221(4) 0.0342(14) Uani 1 1 d . U . . .
N21 N 1.0829(5) 0.9115(4) 0.6625(4) 0.0341(13) Uani 1 1 d . U . . .
H21 H 1.0238 0.9447 0.6848 0.041 Uiso 1 1 calc R . . . .
N24 N 1.0256(5) 0.9883(4) 0.4209(4) 0.0315(13) Uani 1 1 d . U . . .
N15 N 0.9839(5) 0.4165(4) 0.3190(4) 0.0307(12) Uani 1 1 d . U . . .
N25 N 0.6303(5) 0.6610(4) 0.7515(4) 0.0358(13) Uani 1 1 d . U . . .
H25 H 0.6964 0.6813 0.7401 0.043 Uiso 1 1 calc R . . . .
N33 N 0.4240(5) 0.0931(4) 0.3416(4) 0.0347(13) Uani 1 1 d . U . . .
H33 H 0.4862 0.0622 0.3214 0.042 Uiso 1 1 calc R . . . .
N20 N 1.2506(6) 0.8171(4) 0.4967(4) 0.0428(15) Uani 1 1 d . U . . .
H20A H 1.2256 0.8422 0.4590 0.051 Uiso 1 1 calc R . . . .
H20B H 1.3072 0.7762 0.4876 0.051 Uiso 1 1 calc R . . . .
N10 N 0.2030(6) 0.2505(4) -0.0922(4) 0.0376(14) Uani 1 1 d . U . . .
H10 H 0.2905 0.2606 -0.0608 0.045 Uiso 1 1 calc R . . . .
N1 N 0.6194(6) 0.8970(4) 0.2499(4) 0.0353(13) Uani 1 1 d . U . . .
N26 N 0.5222(6) 0.5854(4) 0.6824(4) 0.0319(13) Uani 1 1 d . U . . .
O20 O 0.1828(6) 0.4146(4) 0.7557(4) 0.0592(16) Uani 1 1 d . U . . .
O1 O -0.1195(6) 0.0270(4) -0.2622(4) 0.0571(16) Uani 1 1 d . U . . .
N36 N 0.4671(5) 0.0053(4) 0.5740(4) 0.0342(14) Uani 1 1 d . U . . .
N28 N 0.4071(5) 0.4670(4) 0.5240(4) 0.0345(13) Uani 1 1 d . U . . .
N30 N 0.4563(6) 0.6482(4) 0.8968(4) 0.0393(14) Uani 1 1 d . U . . .
N27 N 0.3368(6) 0.5027(4) 0.6821(4) 0.0399(15) Uani 1 1 d . U . . .
H27A H 0.3096 0.4652 0.6193 0.048 Uiso 1 1 calc R . . . .
H27B H 0.2911 0.4956 0.7147 0.048 Uiso 1 1 calc R . . . .
N13 N 1.1703(6) 0.5033(4) 0.3236(4) 0.0392(14) Uani 1 1 d . U . . .
H13A H 1.1948 0.5403 0.3863 0.047 Uiso 1 1 calc R . . . .
H13B H 1.2175 0.5121 0.2927 0.047 Uiso 1 1 calc R . . . .
N16 N 0.8775(6) 0.3402(4) 0.2481(4) 0.0351(13) Uani 1 1 d . U . . .
H16 H 0.8110 0.3180 0.2578 0.042 Uiso 1 1 calc R . . . .
N7 N 0.1777(5) 0.5702(4) -0.0098(4) 0.0332(13) Uani 1 1 d . U . . .
N4 N 0.2920(6) 0.7529(3) 0.0895(4) 0.0326(13) Uani 1 1 d . U . . .
H4 H 0.2049 0.7414 0.0564 0.039 Uiso 1 1 calc R . . . .
N35 N 0.4079(5) 0.0540(4) 0.5319(4) 0.0343(14) Uani 1 1 d . U . . .
N29 N 0.3982(5) 0.4237(4) 0.4331(4) 0.0358(14) Uani 1 1 d . U . . .
N9 N 0.1287(5) 0.3209(4) -0.0980(4) 0.0326(13) Uani 1 1 d . U . . .
N6 N 0.3209(5) 0.4341(4) 0.0063(4) 0.0336(13) Uani 1 1 d . U . . .
N14 N 1.0564(6) 0.3604(5) 0.1086(4) 0.0404(15) Uani 1 1 d . U . . .
N5 N 0.3819(5) 0.5252(4) 0.0555(4) 0.0347(14) Uani 1 1 d . U . . .
N2 N 0.5942(5) 0.6818(4) 0.1803(4) 0.0395(15) Uani 1 1 d . U . . .
H2A H 0.5755 0.6191 0.1552 0.047 Uiso 1 1 calc R . . . .
H2B H 0.6763 0.7134 0.2201 0.047 Uiso 1 1 calc R . . . .
N12 N -0.1240(7) 0.1093(4) -0.2496(5) 0.0475(16) Uani 1 1 d . U . . .
N31 N 0.1772(6) 0.2470(4) 0.3537(4) 0.0365(14) Uani 1 1 d . U . . .
N19 N 1.3158(6) 0.7484(4) 0.6435(5) 0.0466(16) Uani 1 1 d . U . . .
O23 O 0.1300(6) 0.2473(4) 0.6607(4) 0.0621(16) Uani 1 1 d . U . . .
O22 O 0.0915(6) 0.3415(4) 0.5878(4) 0.0653(17) Uani 1 1 d D U . . .
C12 C 0.9929(6) 0.4600(5) 0.4139(4) 0.0281(14) Uani 1 1 d . U . . .
N11 N -0.0988(6) 0.3236(4) -0.1791(4) 0.0413(15) Uani 1 1 d . U . . .
H11A H -0.0808 0.3863 -0.1542 0.050 Uiso 1 1 calc R . . . .
H11B H -0.1810 0.2917 -0.2181 0.050 Uiso 1 1 calc R . . . .
N32 N 0.2384(5) 0.1754(4) 0.4967(4) 0.0358(14) Uani 1 1 d . U . . .
H32A H 0.2636 0.1509 0.5349 0.043 Uiso 1 1 calc R . . . .
H32B H 0.1776 0.2132 0.5028 0.043 Uiso 1 1 calc R . . . .
C4 C 0.3075(6) 0.5889(4) 0.0457(5) 0.0295(15) Uani 1 1 d . U . . .
C21 C 0.3477(7) 0.1448(5) 0.3062(5) 0.0357(16) Uani 1 1 d . U . . .
C3 C 0.4996(6) 0.7282(5) 0.1582(4) 0.0297(14) Uani 1 1 d . U . . .
C5 C 0.1901(7) 0.4158(4) -0.0470(4) 0.0296(15) Uani 1 1 d . U . . .
C16 C 1.0560(6) 0.9542(4) 0.5406(5) 0.0271(14) Uani 1 1 d . U . . .
C6 C -0.0039(7) 0.2782(5) -0.1583(5) 0.0318(15) Uani 1 1 d . U . . .
C10 C 1.0066(7) 0.3680(5) 0.1787(5) 0.0331(15) Uani 1 1 d . U . . .
C24 C 0.4440(6) 0.0468(5) 0.4606(5) 0.0325(15) Uani 1 1 d . U . . .
C17 C 0.4455(7) 0.5693(5) 0.7273(5) 0.0316(15) Uani 1 1 d . U . . .
C15 C 1.2037(7) 0.8405(5) 0.5662(5) 0.0364(16) Uani 1 1 d . U . . .
C2 C 0.5043(7) 0.8257(4) 0.1886(4) 0.0305(15) Uani 1 1 d . U . . .
C20 C 0.5048(7) 0.6388(5) 0.8253(5) 0.0325(15) Uani 1 1 d . U . . .
C1 C 0.3757(7) 0.8418(5) 0.1432(5) 0.0348(16) Uani 1 1 d . U . . .
C19 C 0.6173(7) 0.6981(5) 0.8391(5) 0.0345(16) Uani 1 1 d . U . . .
C14 C 1.2297(7) 0.8113(5) 0.6357(5) 0.0384(16) Uani 1 1 d . U . . .
C18 C 0.5089(7) 0.5405(5) 0.5872(5) 0.0310(15) Uani 1 1 d . U . . .
C9 C 0.8938(7) 0.3060(5) 0.1615(5) 0.0354(16) Uani 1 1 d . U . . .
C22 C 0.2701(7) 0.1876(4) 0.3650(5) 0.0331(15) Uani 1 1 d . U . . .
C11 C 1.0644(7) 0.4357(5) 0.2765(5) 0.0301(14) Uani 1 1 d . U . . .
O21 O -0.0429(6) 0.3374(6) 0.6726(5) 0.092(2) Uani 1 1 d . U . . .
C8 C 0.1181(8) 0.1636(5) -0.1432(5) 0.0388(17) Uani 1 1 d . U . . .
C23 C 0.2908(6) 0.1557(4) 0.4313(5) 0.0297(14) Uani 1 1 d . U . . .
C7 C -0.0083(7) 0.1799(5) -0.1875(5) 0.0382(16) Uani 1 1 d . U . . .
C13 C 1.1582(7) 0.8588(5) 0.6979(5) 0.0394(17) Uani 1 1 d . U . . .
O10 O 1.4072(7) 0.6619(4) 0.4162(4) 0.0494(16) Uani 0.8 1 d . U P A 1
O7 O 1.3326(7) 0.5883(4) 0.2489(4) 0.0505(17) Uani 0.8 1 d . U P A 1
O8 O 1.3739(7) 0.7548(5) 0.3419(5) 0.0519(17) Uani 0.8 1 d D U P A 1
O9 O 1.5543(7) 0.6702(6) 0.3413(6) 0.077(2) Uani 0.8 1 d . U P A 1
O27 O 0.3954(8) 0.0661(5) -0.0614(6) 0.113(3) Uani 1 1 d . U . . .
H27C H 0.4737 0.1061 -0.0246 0.170 Uiso 1 1 d R . . . .
H27D H 0.3362 0.0730 -0.1061 0.170 Uiso 1 1 d R . . . .
O28 O 0.9964(10) 0.9348(8) 0.8631(8) 0.168(4) Uani 1 1 d . U . . .
H28A H 0.9625 0.8968 0.8734 0.251 Uiso 1 1 d R . . . .
H28B H 0.9772 0.9667 0.8397 0.251 Uiso 1 1 d R . . . .
O29 O 0.9157(10) 0.8753(6) 0.9450(7) 0.152(4) Uani 1 1 d . U . . .
H29A H 0.8385 0.9051 0.9486 0.228 Uiso 1 1 d R . . . .
H29B H 0.8776 0.8222 0.9364 0.228 Uiso 1 1 d R . . . .
O30 O 0.6052(12) 0.1417(9) 0.0682(8) 0.076(4) Uani 0.5 1 d . U P . .
H30A H 0.6903 0.1392 0.0767 0.114 Uiso 0.5 1 d R . P . .
H30B H 0.5680 0.1431 0.1103 0.114 Uiso 0.5 1 d R . P . .
O31 O 0.4964(13) 0.0688(9) 0.1256(8) 0.082(4) Uani 0.5 1 d . U P . .
H31A H 0.4638 0.0897 0.1717 0.123 Uiso 0.5 1 d R . P . .
H31B H 0.4688 0.0671 0.0749 0.123 Uiso 0.5 1 d R . P . .
O32 O 0.9110(16) 1.0527(11) 0.9191(11) 0.097(5) Uani 0.5 1 d . U P . .
H32C H 0.8741 1.0523 0.9583 0.145 Uiso 0.5 1 d G . P . .
H32D H 0.9042 1.1058 0.9173 0.145 Uiso 0.5 1 d G . P . .
O33 O 0.7466(13) 1.0224(11) 0.9905(12) 0.108(5) Uani 0.5 1 d . U P . .
H33A H 0.6868 1.0284 1.0177 0.162 Uiso 0.5 1 d R . P . .
H33B H 0.7020 0.9842 0.9295 0.162 Uiso 0.5 1 d R . P . .
O10A O 1.528(3) 0.6560(16) 0.4161(17) 0.045(5) Uani 0.2 1 d . U P A 2
O7A O 1.442(3) 0.5861(17) 0.2421(18) 0.047(5) Uani 0.2 1 d . U P A 2
O9A O 1.495(3) 0.7573(17) 0.3456(17) 0.045(5) Uani 0.2 1 d . U P A 2
O8A O 1.307(3) 0.6622(18) 0.3313(19) 0.051(5) Uani 0.2 1 d . U P A 2
H22 H 0.04(3) 0.38(3) 0.57(2) 1.2(6) Uiso 1 1 d D . . . .
H8 H 1.319(14) 0.797(10) 0.344(13) 0.27(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
Cl00 O20 1.444(5) . ?
Cl00 O23 1.436(5) . ?
Cl00 O22 1.429(5) . ?
Cl00 O21 1.407(6) . ?
Cl1 O10 1.467(7) . ?
Cl1 O7 1.437(6) . ?
Cl1 O8 1.450(7) . ?
Cl1 O9 1.359(7) . ?
Cl1 O10A 1.55(2) . ?
Cl1 O7A 1.59(2) . ?
Cl1 O9A 1.53(2) . ?
Cl1 O8A 1.21(3) . ?
O5 N1 1.237(7) . ?
O26 C21 1.246(8) . ?
O16 C19 1.236(8) . ?
O14 N30 1.238(7) . ?
O15 N30 1.239(7) . ?
N3 N4 1.406(7) . ?
N3 C4 1.376(8) . ?
N3 C3 1.373(8) . ?
O4 C1 1.235(8) . ?
O6 N1 1.242(7) . ?
O25 N31 1.247(7) . ?
O3 C8 1.246(8) . ?
N23 N24 1.325(7) . ?
N23 C16 1.329(8) . ?
O18 N19 1.239(8) . ?
O24 N31 1.235(7) . ?
O12 N14 1.245(7) . ?
O2 N12 1.236(8) . ?
O17 N19 1.238(8) . ?
N22 N21 1.394(7) . ?
N22 C16 1.382(7) . ?
N22 C15 1.376(8) . ?
O13 C9 1.239(8) . ?
N8 N7 1.335(7) . ?
N8 C5 1.333(8) . ?
O11 N14 1.239(8) . ?
N34 N33 1.400(7) . ?
N34 C24 1.389(8) . ?
N34 C23 1.366(8) . ?
O19 C13 1.250(8) . ?
N17 N18 1.324(7) . ?
N17 C12 1.328(8) . ?
N18 C12 1.333(8) 2_766 ?
N21 C13 1.374(8) . ?
N24 C16 1.342(8) 2_776 ?
N15 N16 1.402(7) . ?
N15 C12 1.382(8) . ?
N15 C11 1.387(8) . ?
N25 N26 1.401(7) . ?
N25 C19 1.361(8) . ?
N33 C21 1.366(8) . ?
N20 C15 1.308(9) . ?
N10 N9 1.400(7) . ?
N10 C8 1.368(8) . ?
N1 C2 1.396(8) . ?
N26 C17 1.367(8) . ?
N26 C18 1.371(8) . ?
O1 N12 1.239(8) . ?
N36 N35 1.326(7) . ?
N36 C24 1.342(8) 2_656 ?
N28 N29 1.321(7) . ?
N28 C18 1.332(8) . ?
N30 C20 1.399(8) . ?
N27 C17 1.313(8) . ?
N13 C11 1.300(8) . ?
N16 C9 1.366(8) . ?
N7 C4 1.334(8) . ?
N4 C1 1.384(8) . ?
N35 C24 1.329(8) . ?
N29 C18 1.345(8) 2_666 ?
N9 C5 1.375(8) . ?
N9 C6 1.384(8) . ?
N6 N5 1.325(7) . ?
N6 C5 1.334(8) . ?
N14 C10 1.394(8) . ?
N5 C4 1.332(8) . ?
N2 C3 1.314(8) . ?
N12 C7 1.396(9) . ?
N31 C22 1.402(8) . ?
N19 C14 1.385(8) . ?
C12 N18 1.333(8) 2_766 ?
N11 C6 1.298(8) . ?
N32 C23 1.295(8) . ?
C21 C22 1.411(9) . ?
C3 C2 1.392(9) . ?
C16 N24 1.342(8) 2_776 ?
C6 C7 1.408(9) . ?
C10 C9 1.417(9) . ?
C10 C11 1.396(9) . ?
C24 N36 1.342(8) 2_656 ?
C17 C20 1.406(9) . ?
C15 C14 1.412(9) . ?
C2 C1 1.428(9) . ?
C20 C19 1.411(9) . ?
C14 C13 1.411(10) . ?
C18 N29 1.345(8) 2_666 ?
C22 C23 1.398(9) . ?
C8 C7 1.405(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O23 Cl00 O20 108.4(3) . . ?
O22 Cl00 O20 109.1(3) . . ?
O22 Cl00 O23 108.8(4) . . ?
O21 Cl00 O20 110.0(4) . . ?
O21 Cl00 O23 110.1(4) . . ?
O21 Cl00 O22 110.5(4) . . ?
O7 Cl1 O10 106.9(4) . . ?
O7 Cl1 O8 107.0(4) . . ?
O8 Cl1 O10 105.9(4) . . ?
O9 Cl1 O10 111.0(5) . . ?
O9 Cl1 O7 112.7(5) . . ?
O9 Cl1 O8 112.9(5) . . ?
O10A Cl1 O7A 101.6(13) . . ?
O9A Cl1 O10A 102.4(13) . . ?
O9A Cl1 O7A 100.8(14) . . ?
O8A Cl1 O10A 116.7(16) . . ?
O8A Cl1 O7A 112.0(16) . . ?
O8A Cl1 O9A 120.7(16) . . ?
C4 N3 N4 118.7(5) . . ?
C3 N3 N4 109.7(5) . . ?
C3 N3 C4 131.6(6) . . ?
N24 N23 C16 117.1(5) . . ?
C16 N22 N21 119.7(5) . . ?
C15 N22 N21 109.5(5) . . ?
C15 N22 C16 130.7(6) . . ?
C5 N8 N7 116.2(5) . . ?
C24 N34 N33 119.1(5) . . ?
C23 N34 N33 110.7(5) . . ?
C23 N34 C24 130.2(6) . . ?
N18 N17 C12 116.1(5) . . ?
N17 N18 C12 116.9(5) . 2_766 ?
C13 N21 N22 109.1(6) . . ?
N23 N24 C16 115.9(5) . 2_776 ?
C12 N15 N16 119.5(5) . . ?
C12 N15 C11 130.9(6) . . ?
C11 N15 N16 109.6(5) . . ?
C19 N25 N26 109.4(5) . . ?
C21 N33 N34 107.8(5) . . ?
C8 N10 N9 109.2(6) . . ?
O5 N1 O6 122.4(6) . . ?
O5 N1 C2 120.0(6) . . ?
O6 N1 C2 117.6(6) . . ?
C17 N26 N25 109.0(5) . . ?
C17 N26 C18 131.0(6) . . ?
C18 N26 N25 120.1(5) . . ?
N35 N36 C24 116.7(5) . 2_656 ?
N29 N28 C18 117.1(5) . . ?
O14 N30 O15 122.4(6) . . ?
O14 N30 C20 118.8(6) . . ?
O15 N30 C20 118.8(6) . . ?
C9 N16 N15 108.8(5) . . ?
C4 N7 N8 116.8(5) . . ?
C1 N4 N3 108.6(5) . . ?
N36 N35 C24 116.3(5) . . ?
N28 N29 C18 116.8(6) . 2_666 ?
C5 N9 N10 120.2(5) . . ?
C5 N9 C6 130.3(6) . . ?
C6 N9 N10 109.5(5) . . ?
N5 N6 C5 116.4(5) . . ?
O12 N14 C10 119.0(6) . . ?
O11 N14 O12 122.7(6) . . ?
O11 N14 C10 118.4(6) . . ?
N6 N5 C4 117.0(5) . . ?
O2 N12 O1 122.3(6) . . ?
O2 N12 C7 119.3(7) . . ?
O1 N12 C7 118.4(7) . . ?
O25 N31 C22 119.0(6) . . ?
O24 N31 O25 122.2(5) . . ?
O24 N31 C22 118.9(6) . . ?
O18 N19 C14 118.2(7) . . ?
O17 N19 O18 122.0(6) . . ?
O17 N19 C14 119.7(7) . . ?
N17 C12 N18 127.0(6) . 2_766 ?
N17 C12 N15 116.1(6) . . ?
N18 C12 N15 116.9(6) 2_766 . ?
N7 C4 N3 115.9(6) . . ?
N5 C4 N3 117.6(6) . . ?
N5 C4 N7 126.5(6) . . ?
O26 C21 N33 122.0(7) . . ?
O26 C21 C22 131.7(6) . . ?
N33 C21 C22 106.3(6) . . ?
N3 C3 C2 106.2(6) . . ?
N2 C3 N3 123.3(6) . . ?
N2 C3 C2 130.5(6) . . ?
N8 C5 N9 117.2(6) . . ?
N8 C5 N6 127.1(6) . . ?
N6 C5 N9 115.6(6) . . ?
N23 C16 N22 117.6(6) . . ?
N23 C16 N24 127.0(6) . 2_776 ?
N24 C16 N22 115.5(6) 2_776 . ?
N9 C6 C7 104.7(6) . . ?
N11 C6 N9 124.9(6) . . ?
N11 C6 C7 130.3(6) . . ?
N14 C10 C9 125.0(7) . . ?
N14 C10 C11 124.6(6) . . ?
C11 C10 C9 110.3(6) . . ?
N36 C24 N34 115.0(6) 2_656 . ?
N35 C24 N34 118.0(6) . . ?
N35 C24 N36 127.0(6) . 2_656 ?
N26 C17 C20 106.1(6) . . ?
N27 C17 N26 123.9(6) . . ?
N27 C17 C20 130.1(6) . . ?
N22 C15 C14 105.7(6) . . ?
N20 C15 N22 123.8(6) . . ?
N20 C15 C14 130.5(7) . . ?
N1 C2 C1 124.5(6) . . ?
C3 C2 N1 125.3(6) . . ?
C3 C2 C1 110.0(6) . . ?
N30 C20 C17 124.6(6) . . ?
N30 C20 C19 125.9(7) . . ?
C17 C20 C19 109.5(6) . . ?
O4 C1 N4 123.0(6) . . ?
O4 C1 C2 131.6(6) . . ?
N4 C1 C2 105.3(6) . . ?
O16 C19 N25 123.3(6) . . ?
O16 C19 C20 130.8(7) . . ?
N25 C19 C20 105.9(6) . . ?
N19 C14 C15 125.1(7) . . ?
N19 C14 C13 125.4(7) . . ?
C13 C14 C15 109.5(6) . . ?
N28 C18 N26 118.3(6) . . ?
N28 C18 N29 126.1(6) . 2_666 ?
N29 C18 N26 115.6(6) 2_666 . ?
O13 C9 N16 122.7(7) . . ?
O13 C9 C10 131.3(7) . . ?
N16 C9 C10 105.9(6) . . ?
N31 C22 C21 125.2(6) . . ?
C23 C22 N31 124.6(6) . . ?
C23 C22 C21 110.0(6) . . ?
N15 C11 C10 105.1(6) . . ?
N13 C11 N15 124.1(6) . . ?
N13 C11 C10 130.8(6) . . ?
O3 C8 N10 122.0(7) . . ?
O3 C8 C7 132.2(7) . . ?
N10 C8 C7 105.8(6) . . ?
N34 C23 C22 105.0(6) . . ?
N32 C23 N34 124.7(6) . . ?
N32 C23 C22 130.3(6) . . ?
N12 C7 C6 124.3(7) . . ?
N12 C7 C8 125.1(7) . . ?
C8 C7 C6 110.6(6) . . ?
O19 C13 N21 122.9(7) . . ?
O19 C13 C14 131.1(7) . . ?
N21 C13 C14 106.0(6) . . ?

_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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2390034'
loop_
_audit_author_name
_audit_author_address
'Xiue Jiang'
;Northwestern Polytechnical University
China
;
_audit_update_record             
;
2024-10-10 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;
_audit_creation_date             2024-09-05
_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         'Cl O3.97, C9 H9 N12 O6'
_chemical_formula_sum            'C9 H9 Cl N12 O9.97'
_chemical_formula_weight         480.22
_chemical_absolute_configuration ad
_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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x, -y, z+1/2'
3 'x+1/2, y+1/2, z'
4 'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   15.6357(6)
_cell_length_b                   5.8232(3)
_cell_length_c                   18.7157(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.011(2)
_cell_angle_gamma                90.00
_cell_volume                     1678.12(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9063
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      27.489
_cell_measurement_theta_min      2.210
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1338 before and 0.0573 after correction.
The Ratio of minimum to maximum transmission is 0.8719.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.901
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             975
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22346
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.21
_diffrn_ambient_temperature      302.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3462
_reflns_number_total             3773
_reflns_threshold_expression     >2sigma(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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(7)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3773
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0870P)²+0.9230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1334
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 N005(H005), N00B(H00B), N00E(H00E)
2.b X=CH2 refined with riding coordinates:
 N00G(H00a,H00c), N00L(H00d,H00f), N00P(H00g,H00h)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl01 Cl 0.54496(4) 0.03667(13) 0.64136(4) 0.03815(19) Uani 1 d . . .
O002 O 0.75949(17) 0.1328(4) 0.28459(13) 0.0448(5) Uani 1 d . . .
O003 O 0.78635(16) -0.1387(4) 0.36546(13) 0.0441(5) Uani 1 d . . .
O004 O 0.35739(17) 0.4270(4) 0.68353(14) 0.0462(6) Uani 1 d . . .
N005 N 0.47612(16) 0.5030(4) 0.46172(13) 0.0284(5) Uani 1 d . . .
H005 H 0.4859 0.3975 0.4943 0.034 Uiso 1 calc . . R
N006 N 0.37354(15) 0.6679(4) 0.51926(13) 0.0293(5) Uani 1 d . . .
N007 N 0.74398(16) 0.0284(4) 0.33965(15) 0.0319(5) Uani 1 d . . .
N008 N 0.39846(16) 0.8387(4) 0.41427(13) 0.0306(5) Uani 1 d . . .
O009 O 0.26178(16) 0.8210(5) 0.71528(13) 0.0468(6) Uani 1 d . . .
N00A N 0.50460(17) 0.6743(4) 0.35216(14) 0.0332(5) Uani 1 d . . .
N00B N 0.39040(16) 0.5013(4) 0.57288(15) 0.0318(5) Uani 1 d . . .
H00B H 0.4224 0.3819 0.5715 0.038 Uiso 1 calc . . R
O00C O 0.6790(2) -0.1349(5) 0.47751(15) 0.0597(8) Uani 1 d . . .
N00D N 0.57770(16) 0.3504(4) 0.40107(14) 0.0308(5) Uani 1 d . . .
N00E N 0.59120(18) 0.1772(4) 0.45308(15) 0.0379(6) Uani 1 d . . .
H00E H 0.5639 0.1650 0.4890 0.046 Uiso 1 calc . . R
N00F N 0.25499(17) 0.8825(5) 0.65166(15) 0.0370(6) Uani 1 d . . .
N00G N 0.28809(19) 1.0052(5) 0.49891(18) 0.0394(6) Uani 1 d . . .
H00A H 0.3041 1.0259 0.4577 0.047 Uiso 1 calc . . R
H00C H 0.2530 1.1006 0.5137 0.047 Uiso 1 calc . . R
O00H O 0.4919(2) 0.1027(6) 0.57309(16) 0.0663(8) Uani 1 d A . .
C00I C 0.41868(16) 0.6701(4) 0.46170(14) 0.0264(5) Uani 1 d . . .
C00J C 0.51707(18) 0.5191(4) 0.40464(16) 0.0275(5) Uani 1 d . . .
C00K C 0.63044(16) 0.3147(5) 0.35010(15) 0.0279(5) Uani 1 d . . .
N00L N 0.63089(19) 0.4462(5) 0.29438(15) 0.0405(6) Uani 1 d . . .
H00D H 0.5970 0.5635 0.2876 0.049 Uiso 1 calc . . R
H00F H 0.6651 0.4163 0.2642 0.049 Uiso 1 calc . . R
O00M O 0.2140(2) 1.0492(5) 0.62664(19) 0.0624(8) Uani 1 d . . .
C00N C 0.31724(17) 0.8277(5) 0.53931(16) 0.0296(5) Uani 1 d . . .
C00O C 0.34887(19) 0.5565(5) 0.62681(17) 0.0305(6) Uani 1 d . . .
N00P N 0.4282(2) 0.9971(5) 0.30975(16) 0.0410(7) Uani 1 d . . .
H00G H 0.4561 1.0004 0.2740 0.049 Uiso 1 calc . . R
H00H H 0.3898 1.1004 0.3133 0.049 Uiso 1 calc . . R
C00Q C 0.67901(18) 0.1165(5) 0.37362(15) 0.0299(5) Uani 1 d . . .
C00R C 0.30180(17) 0.7578(5) 0.60718(15) 0.0293(5) Uani 1 d . . .
C00S C 0.6541(2) 0.0290(5) 0.43891(18) 0.0346(6) Uani 1 d . . .
C00T C 0.44422(18) 0.8339(5) 0.35904(15) 0.0301(6) Uani 1 d . . .
O00U O 0.6316(2) 0.0028(8) 0.6304(2) 0.0878(12) Uani 1 d A . .
O00V O 0.5432(3) 0.2087(12) 0.6934(3) 0.121(3) Uani 0.968(14) d A 1 .
O2 O 0.5103(4) -0.1593(11) 0.6666(4) 0.150(3) Uani 1 d A 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
Cl01 O00H 1.449(3) . ?
Cl01 O00U 1.419(4) . ?
Cl01 O00V 1.400(4) . ?
Cl01 O2 1.382(4) . ?
O002 N007 1.256(4) . ?
O003 N007 1.228(4) . ?
O004 C00O 1.290(4) . ?
N005 H005 0.8600 . ?
N005 C00I 1.324(3) . ?
N005 C00J 1.341(4) . ?
N006 N00B 1.388(3) . ?
N006 C00I 1.387(3) . ?
N006 C00N 1.377(3) . ?
N007 C00Q 1.387(3) . ?
N008 C00I 1.324(3) . ?
N008 C00T 1.356(4) . ?
O009 N00F 1.230(4) . ?
N00A C00J 1.324(4) . ?
N00A C00T 1.347(3) . ?
N00B H00B 0.8600 . ?
N00B C00O 1.331(4) . ?
O00C C00S 1.219(4) . ?
N00D N00E 1.392(3) . ?
N00D C00J 1.375(3) . ?
N00D C00K 1.381(3) . ?
N00E H00E 0.8600 . ?
N00E C00S 1.369(4) . ?
N00F O00M 1.212(4) . ?
N00F C00R 1.403(3) . ?
N00G H00A 0.8600 . ?
N00G H00C 0.8600 . ?
N00G C00N 1.314(4) . ?
C00K N00L 1.295(4) . ?
C00K C00Q 1.409(4) . ?
N00L H00D 0.8600 . ?
N00L H00F 0.8600 . ?
C00N C00R 1.394(4) . ?
C00O C00R 1.399(4) . ?
N00P H00G 0.8600 . ?
N00P H00H 0.8600 . ?
N00P C00T 1.318(4) . ?
C00Q C00S 1.439(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
O00U Cl01 O00H 108.9(2) . . ?
O00V Cl01 O00H 110.2(3) . . ?
O00V Cl01 O00U 109.5(3) . . ?
O2 Cl01 O00H 108.8(3) . . ?
O2 Cl01 O00U 112.1(4) . . ?
O2 Cl01 O00V 107.3(5) . . ?
C00I N005 H005 124.3 . . ?
C00I N005 C00J 111.5(2) . . ?
C00J N005 H005 124.3 . . ?
C00I N006 N00B 120.6(2) . . ?
C00N N006 N00B 109.0(2) . . ?
C00N N006 C00I 129.9(2) . . ?
O002 N007 C00Q 117.3(2) . . ?
O003 N007 O002 122.6(2) . . ?
O003 N007 C00Q 120.1(3) . . ?
C00I N008 C00T 113.6(2) . . ?
C00J N00A C00T 114.5(2) . . ?
N006 N00B H00B 125.6 . . ?
C00O N00B N006 108.9(2) . . ?
C00O N00B H00B 125.6 . . ?
C00J N00D N00E 120.4(2) . . ?
C00J N00D C00K 129.8(2) . . ?
C00K N00D N00E 109.7(2) . . ?
N00D N00E H00E 124.8 . . ?
C00S N00E N00D 110.4(2) . . ?
C00S N00E H00E 124.8 . . ?
O009 N00F C00R 117.2(3) . . ?
O00M N00F O009 123.9(3) . . ?
O00M N00F C00R 118.7(3) . . ?
H00A N00G H00C 120.0 . . ?
C00N N00G H00A 120.0 . . ?
C00N N00G H00C 120.0 . . ?
N005 C00I N006 115.5(2) . . ?
N005 C00I N008 128.9(3) . . ?
N008 C00I N006 115.7(2) . . ?
N005 C00J N00D 114.7(2) . . ?
N00A C00J N005 127.6(2) . . ?
N00A C00J N00D 117.7(2) . . ?
N00D C00K C00Q 105.2(2) . . ?
N00L C00K N00D 123.7(2) . . ?
N00L C00K C00Q 131.1(2) . . ?
C00K N00L H00D 120.0 . . ?
C00K N00L H00F 120.0 . . ?
H00D N00L H00F 120.0 . . ?
N006 C00N C00R 105.7(2) . . ?
N00G C00N N006 123.3(3) . . ?
N00G C00N C00R 131.0(3) . . ?
O004 C00O N00B 119.3(3) . . ?
O004 C00O C00R 132.9(3) . . ?
N00B C00O C00R 107.9(2) . . ?
H00G N00P H00H 120.0 . . ?
C00T N00P H00G 120.0 . . ?
C00T N00P H00H 120.0 . . ?
N007 C00Q C00K 123.9(3) . . ?
N007 C00Q C00S 125.9(3) . . ?
C00K C00Q C00S 110.2(2) . . ?
C00N C00R N00F 125.5(3) . . ?
C00N C00R C00O 108.5(2) . . ?
C00O C00R N00F 125.6(3) . . ?
O00C C00S N00E 123.0(3) . . ?
O00C C00S C00Q 132.4(3) . . ?
N00E C00S C00Q 104.5(2) . . ?
N00A C00T N008 124.0(2) . . ?
N00P C00T N008 117.2(2) . . ?
N00P C00T N00A 118.8(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
