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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_220621g
_audit_block_doi                 10.5517/ccdc.csd.cc2h0bzv
_database_code_depnum_ccdc_archive 'CCDC 2294247'
loop_
_audit_author_name
_audit_author_address
luzujia
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-09-11 deposited with the CCDC.	2024-01-15 downloaded from the CCDC.
;
_audit_creation_date             2022-07-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H16 Cl2 Cu N8 O8'
_chemical_formula_sum            'C12 H16 Cl2 Cu N8 O8'
_chemical_formula_weight         534.77
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/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'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.4222(15)
_cell_length_b                   9.8977(11)
_cell_length_c                   15.7318(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.349(5)
_cell_angle_gamma                90.00
_cell_volume                     2029.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2261
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.239
_cell_measurement_theta_min      2.584
_exptl_absorpt_coefficient_mu    1.400
_exptl_absorpt_correction_T_max  0.7968
_exptl_absorpt_correction_T_min  0.6789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.750
_exptl_crystal_density_meas      1.750
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1084
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4929
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.58
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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                1473
_reflns_number_total             1786
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.851
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1786
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.121
_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)+(0.0602P)²+4.2619P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1202
_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
2. Uiso/Uaniso restraints and constraints
Cl1 \\sim O1 \\sim O2 \\sim O3 \\sim O4: within 3.8A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 3.8A
3.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4), C1(H1), C2(H2A), C3(H3), C4(H4A), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu1 Cu 0.2500 0.2500 0.5000 0.0355(2) Uani 1 d . . 2 S T P
Cl1 Cl 0.09538(7) -0.06852(10) 0.43692(7) 0.0443(3) Uani 1 d . . 1 . U .
N1 N 0.1250(2) 0.3624(3) 0.4395(2) 0.0401(8) Uani 1 d . . 1 . . .
N2 N 0.1230(3) 0.4962(4) 0.4445(3) 0.0687(12) Uani 1 d . . 1 . . .
H2 H 0.1759 0.5457 0.4753 0.082 Uiso 1 calc . . 1 R . .
N3 N 0.2544(2) 0.2257(3) 0.3754(2) 0.0410(8) Uani 1 d . . 1 . . .
N4 N 0.3236(3) 0.2874(4) 0.3540(3) 0.0492(9) Uani 1 d . . 1 . . .
H4 H 0.3709 0.3396 0.3918 0.059 Uiso 1 calc . . 1 R . .
O1 O 0.1445(2) 0.0507(3) 0.4874(2) 0.0632(9) Uani 1 d . . 1 . U .
O2 O 0.1687(3) -0.1415(4) 0.4195(3) 0.0970(13) Uani 1 d . . 1 . U .
O3 O 0.0124(3) -0.0301(5) 0.3536(3) 0.1084(16) Uani 1 d . . 1 . U .
O4 O 0.0586(3) -0.1444(4) 0.4912(3) 0.0736(10) Uani 1 d . . 1 . U .
C1 C 0.0282(3) 0.3277(5) 0.3882(3) 0.0561(12) Uani 1 d . . 1 . . .
H1 H 0.0049 0.2393 0.3735 0.067 Uiso 1 calc . . 1 R . .
C2 C -0.0322(4) 0.4391(5) 0.3601(4) 0.0786(17) Uani 1 d . . 1 . . .
H2A H -0.1026 0.4416 0.3231 0.094 Uiso 1 calc . . 1 R . .
C3 C 0.0294(4) 0.5432(5) 0.3961(5) 0.087(2) Uani 1 d . . 1 . . .
H3 H 0.0103 0.6337 0.3886 0.105 Uiso 1 calc . . 1 R . .
C4 C 0.1965(3) 0.1573(5) 0.2992(3) 0.0553(12) Uani 1 d . . 1 . . .
H4A H 0.1407 0.1043 0.2929 0.066 Uiso 1 calc . . 1 R . .
C5 C 0.2297(4) 0.1752(6) 0.2311(3) 0.0619(13) Uani 1 d . . 1 . . .
H5 H 0.2023 0.1373 0.1712 0.074 Uiso 1 calc . . 1 R . .
C6 C 0.3107(4) 0.2592(5) 0.2685(3) 0.0574(12) Uani 1 d . . 1 . . .
H6 H 0.3501 0.2912 0.2389 0.069 Uiso 1 calc . . 1 R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.981(3) 7_556 ?
Cu1 N1 1.981(3) . ?
Cu1 N3 2.002(3) 7_556 ?
Cu1 N3 2.002(3) . ?
Cu1 O1 2.447(3) . ?
Cl1 O1 1.429(3) . ?
Cl1 O2 1.401(4) . ?
Cl1 O3 1.397(4) . ?
Cl1 O4 1.400(3) . ?
N1 N2 1.327(5) . ?
N1 C1 1.325(5) . ?
N2 H2 0.8600 . ?
N2 C3 1.319(6) . ?
N3 N4 1.330(5) . ?
N3 C4 1.317(5) . ?
N4 H4 0.8600 . ?
N4 C6 1.308(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.357(6) . ?
C2 H2A 0.9300 . ?
C2 C3 1.319(7) . ?
C3 H3 0.9300 . ?
C4 H4A 0.9300 . ?
C4 C5 1.360(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.346(7) . ?
C6 H6 0.9300 . ?

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
N1 Cu1 N1 180.000(1) 7_556 . ?
N1 Cu1 N3 89.92(13) . 7_556 ?
N1 Cu1 N3 90.08(13) . . ?
N1 Cu1 N3 90.08(13) 7_556 7_556 ?
N1 Cu1 N3 89.92(13) 7_556 . ?
N1 Cu1 O1 89.58(12) 7_556 . ?
N1 Cu1 O1 90.42(12) . . ?
N3 Cu1 N3 180.0 7_556 . ?
N3 Cu1 O1 84.10(12) 7_556 . ?
N3 Cu1 O1 95.90(12) . . ?
O2 Cl1 O1 107.3(2) . . ?
O3 Cl1 O1 108.6(3) . . ?
O3 Cl1 O2 111.8(3) . . ?
O3 Cl1 O4 108.8(3) . . ?
O4 Cl1 O1 109.3(2) . . ?
O4 Cl1 O2 110.9(3) . . ?
N2 N1 Cu1 124.7(3) . . ?
C1 N1 Cu1 130.7(3) . . ?
C1 N1 N2 104.6(3) . . ?
N1 N2 H2 124.4 . . ?
C3 N2 N1 111.1(4) . . ?
C3 N2 H2 124.4 . . ?
N4 N3 Cu1 122.3(3) . . ?
C4 N3 Cu1 132.8(3) . . ?
C4 N3 N4 104.9(4) . . ?
N3 N4 H4 124.1 . . ?
C6 N4 N3 111.8(4) . . ?
C6 N4 H4 124.1 . . ?
Cl1 O1 Cu1 148.6(2) . . ?
N1 C1 H1 124.8 . . ?
N1 C1 C2 110.5(4) . . ?
C2 C1 H1 124.8 . . ?
C1 C2 H2A 127.0 . . ?
C3 C2 C1 105.9(4) . . ?
C3 C2 H2A 127.0 . . ?
N2 C3 C2 107.9(4) . . ?
N2 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
N3 C4 H4A 124.7 . . ?
N3 C4 C5 110.6(4) . . ?
C5 C4 H4A 124.7 . . ?
C4 C5 H5 127.2 . . ?
C6 C5 C4 105.5(4) . . ?
C6 C5 H5 127.2 . . ?
N4 C6 C5 107.2(4) . . ?
N4 C6 H6 126.4 . . ?
C5 C6 H6 126.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 N1 N2 C3 178.9(4) . . . . ?
Cu1 N1 C1 C2 -179.3(4) . . . . ?
Cu1 N3 N4 C6 -178.6(3) . . . . ?
Cu1 N3 C4 C5 178.6(3) . . . . ?
N1 Cu1 N1 N2 -27(37) 7_556 . . . ?
N1 Cu1 N1 C1 154(37) 7_556 . . . ?
N1 Cu1 N3 N4 106.9(3) . . . . ?
N1 Cu1 N3 N4 -73.1(3) 7_556 . . . ?
N1 Cu1 N3 C4 -70.8(4) . . . . ?
N1 Cu1 N3 C4 109.2(4) 7_556 . . . ?
N1 Cu1 O1 Cl1 96.4(4) . . . . ?
N1 Cu1 O1 Cl1 -83.6(4) 7_556 . . . ?
N1 N2 C3 C2 1.5(8) . . . . ?
N1 C1 C2 C3 -0.6(7) . . . . ?
N2 N1 C1 C2 1.4(6) . . . . ?
N3 Cu1 N1 N2 76.8(4) 7_556 . . . ?
N3 Cu1 N1 N2 -103.2(4) . . . . ?
N3 Cu1 N1 C1 -102.3(4) 7_556 . . . ?
N3 Cu1 N1 C1 77.7(4) . . . . ?
N3 Cu1 N3 N4 -1(29) 7_556 . . . ?
N3 Cu1 N3 C4 -179(29) 7_556 . . . ?
N3 Cu1 O1 Cl1 6.3(4) . . . . ?
N3 Cu1 O1 Cl1 -173.7(4) 7_556 . . . ?
N3 N4 C6 C5 0.0(5) . . . . ?
N3 C4 C5 C6 -0.6(6) . . . . ?
N4 N3 C4 C5 0.6(5) . . . . ?
O1 Cu1 N1 N2 160.9(4) . . . . ?
O1 Cu1 N1 C1 -18.2(4) . . . . ?
O1 Cu1 N3 N4 -162.6(3) . . . . ?
O1 Cu1 N3 C4 19.6(4) . . . . ?
O2 Cl1 O1 Cu1 50.2(5) . . . . ?
O3 Cl1 O1 Cu1 -70.9(5) . . . . ?
O4 Cl1 O1 Cu1 170.6(4) . . . . ?
C1 N1 N2 C3 -1.8(6) . . . . ?
C1 C2 C3 N2 -0.5(8) . . . . ?
C4 N3 N4 C6 -0.4(5) . . . . ?
C4 C5 C6 N4 0.3(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_220708f
_audit_block_doi                 10.5517/ccdc.csd.cc2h7tsc
_database_code_depnum_ccdc_archive 'CCDC 2301433'
loop_
_audit_author_name
_audit_author_address
luzujia
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-10-16 deposited with the CCDC.	2024-01-15 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 Cu N10 O6'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C12 H16 Cu N10 O6'
_chemical_formula_iupac          ?
_chemical_formula_weight         459.90
_chemical_compound_source        'see text'

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'
Cu Cu 0.3201 1.2651 ' 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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_Int_Tables_number      15

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+z

_cell_length_a                   13.6445(13)
_cell_length_b                   9.8750(9)
_cell_length_c                   14.6405(14)
_cell_angle_alpha                90
_cell_angle_beta                 112.024(5)
_cell_angle_gamma                90
_cell_volume                     1828.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    2545
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      28.14
_cell_special_details            
;
 
;

_exptl_crystal_description       Block
_exptl_crystal_colour            ?

_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             940
_exptl_absorpt_coefficient_mu    1.251
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA,
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  0.635
_exptl_absorpt_correction_T_max  0.770

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 18.4

# number of measured reflections (redundant set)
_diffrn_reflns_number            4264
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             1604
# number of observed reflections (> n sig(I))
_reflns_number_gt                1364
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
'Locally modified CAD4 Software (Enraf-Nonius, 1989)'
_computing_cell_refinement       'SET4 (de Boer & Duisenberg, 1984)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0693P)²+3.3521P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom


# Permitted for _refine_ls_hydrogen_treatment :
# refall  - refined all H parameters
# refxyz  - refined H coordinates only
# refU    - refined H U only
# noref   - no refinement of H parameters
# constr  - H parameters constrained
# mixed   - some constrained, some independent
# undef   - H-atom parameters not defined
_refine_ls_hydrogen_treatment    mixed

_refine_ls_extinction_method     shelxl
_refine_ls_extinction_coef       0.030(2)
_refine_ls_extinction_expression FC^*^=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4^
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         1604
_refine_ls_number_parameters     134
_refine_ls_number_restraints     18
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1251
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.822
_refine_diff_density_rms         0.081

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu Uani 0.25000 0.25000 0.50000 1.000 0.0343(2) d S . .
O1 O Uani 0.1274(2) 0.4320(3) 0.4839(2) 1.000 0.0625(10) d U . .
O2 O Uani 0.1562(3) 0.6322(4) 0.4535(3) 1.000 0.0891(16) d U . .
O3 O Uani 0.0063(3) 0.5437(5) 0.3743(3) 1.000 0.1048(16) d U . .
N1 N Uani 0.2522(2) 0.2741(3) 0.3648(2) 1.000 0.0375(9) d . . .
N2 N Uani 0.3233(2) 0.2124(3) 0.3371(2) 1.000 0.0438(10) d . . .
N3 N Uani 0.1264(2) 0.1266(3) 0.4440(2) 1.000 0.0380(9) d . . .
N4 N Uani 0.1341(2) -0.0085(3) 0.4418(2) 1.000 0.0462(10) d . . .
N5 N Uani 0.0921(3) 0.5350(3) 0.4355(2) 1.000 0.0486(11) d U . .
C1 C Uani 0.1918(3) 0.3439(4) 0.2876(3) 1.000 0.0469(11) d . . .
C2 C Uani 0.2246(3) 0.3261(5) 0.2102(3) 1.000 0.0557(15) d . . .
C3 C Uani 0.3084(4) 0.2417(4) 0.2443(3) 1.000 0.0538(16) d . . .
C4 C Uani 0.0255(3) 0.1538(4) 0.3967(3) 1.000 0.0476(11) d . . .
C5 C Uani -0.0309(3) 0.0353(5) 0.3644(3) 1.000 0.0600(16) d . . .
C6 C Uani 0.0401(3) -0.0636(4) 0.3942(3) 1.000 0.0537(14) d . . .
H1 H Uiso 0.13510 0.39770 0.28560 1.000 0.0560 c R . .
H2 H Uiso 0.37260 0.16030 0.37440 1.000 0.0530 c R . .
H2A H Uiso 0.19520 0.36410 0.14770 1.000 0.0670 c R . .
H3 H Uiso 0.34820 0.21010 0.20920 1.000 0.0650 c R . .
H4 H Uiso 0.19210 -0.05330 0.46760 1.000 0.0550 c R . .
H4A H Uiso -0.00370 0.24020 0.38640 1.000 0.0570 c R . .
H5 H Uiso -0.10320 0.02670 0.32920 1.000 0.0720 c R . .
H6 H Uiso 0.02610 -0.15570 0.38360 1.000 0.0650 c R . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 2.406(3) . . yes
Cu1 N1 2.005(3) . . yes
Cu1 N3 1.991(3) . . yes
Cu1 O1 2.406(3) . 7_556 yes
Cu1 N1 2.005(3) . 7_556 yes
Cu1 N3 1.991(3) . 7_556 yes
O1 N5 1.230(4) . . yes
O2 N5 1.258(5) . . yes
O3 N5 1.181(6) . . yes
N1 N2 1.331(4) . . yes
N1 C1 1.317(5) . . yes
N2 C3 1.328(5) . . yes
N3 N4 1.340(4) . . yes
N3 C4 1.316(5) . . yes
N4 C6 1.325(5) . . yes
N2 H2 0.8600 . . no
N4 H4 0.8600 . . no
C1 C2 1.377(6) . . no
C2 C3 1.350(7) . . no
C4 C5 1.383(6) . . no
C5 C6 1.329(6) . . no
C1 H1 0.9300 . . no
C2 H2A 0.9300 . . no
C3 H3 0.9300 . . no
C4 H4A 0.9300 . . no
C5 H5 0.9300 . . no
C6 H6 0.9300 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N1 94.70(11) . . . yes
O1 Cu1 N3 88.08(11) . . . yes
O1 Cu1 O1 180.00 . . 7_556 yes
O1 Cu1 N1 85.30(11) . . 7_556 yes
O1 Cu1 N3 91.93(11) . . 7_556 yes
N1 Cu1 N3 89.43(12) . . . yes
O1 Cu1 N1 85.30(11) 7_556 . . yes
N1 Cu1 N1 180.00 . . 7_556 yes
N1 Cu1 N3 90.57(12) . . 7_556 yes
O1 Cu1 N3 91.93(11) 7_556 . . yes
N1 Cu1 N3 90.57(12) 7_556 . . yes
N3 Cu1 N3 180.00 . . 7_556 yes
O1 Cu1 N1 94.70(11) 7_556 . 7_556 yes
O1 Cu1 N3 88.08(11) 7_556 . 7_556 yes
N1 Cu1 N3 89.43(12) 7_556 . 7_556 yes
Cu1 O1 N5 141.4(3) . . . yes
Cu1 N1 N2 121.9(2) . . . yes
Cu1 N1 C1 132.3(3) . . . yes
N2 N1 C1 105.7(3) . . . yes
N1 N2 C3 111.3(3) . . . yes
Cu1 N3 N4 123.9(2) . . . yes
Cu1 N3 C4 130.5(3) . . . yes
N4 N3 C4 105.5(3) . . . yes
N3 N4 C6 110.6(3) . . . yes
O1 N5 O2 114.8(4) . . . yes
O1 N5 O3 124.1(4) . . . yes
O2 N5 O3 121.1(4) . . . yes
C3 N2 H2 124.00 . . . no
N1 N2 H2 124.00 . . . no
N3 N4 H4 125.00 . . . no
C6 N4 H4 125.00 . . . no
N1 C1 C2 110.4(4) . . . yes
C1 C2 C3 105.4(4) . . . no
N2 C3 C2 107.2(4) . . . yes
N3 C4 C5 110.2(4) . . . yes
C4 C5 C6 105.4(4) . . . no
N4 C6 C5 108.3(4) . . . yes
N1 C1 H1 125.00 . . . no
C2 C1 H1 125.00 . . . no
C1 C2 H2A 127.00 . . . no
C3 C2 H2A 127.00 . . . no
N2 C3 H3 126.00 . . . no
C2 C3 H3 126.00 . . . no
N3 C4 H4A 125.00 . . . no
C5 C4 H4A 125.00 . . . no
C4 C5 H5 127.00 . . . no
C6 C5 H5 127.00 . . . no
N4 C6 H6 126.00 . . . no
C5 C6 H6 126.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu1 O1 N5 -20.1(4) . . . . no
N3 Cu1 O1 N5 -109.4(4) . . . . no
N1 Cu1 O1 N5 159.9(4) 7_556 . . . no
N3 Cu1 O1 N5 70.6(4) 7_556 . . . no
O1 Cu1 N1 N2 168.3(3) . . . . no
O1 Cu1 N1 C1 -12.7(4) . . . . no
N3 Cu1 N1 N2 -103.7(3) . . . . no
N3 Cu1 N1 C1 75.3(4) . . . . no
O1 Cu1 N1 N2 -11.7(3) 7_556 . . . no
O1 Cu1 N1 C1 167.3(4) 7_556 . . . no
N3 Cu1 N1 N2 76.3(3) 7_556 . . . no
N3 Cu1 N1 C1 -104.7(4) 7_556 . . . no
O1 Cu1 N3 N4 -170.5(3) . . . . no
O1 Cu1 N3 C4 15.1(3) . . . . no
N1 Cu1 N3 N4 94.8(3) . . . . no
N1 Cu1 N3 C4 -79.6(3) . . . . no
O1 Cu1 N3 N4 9.5(3) 7_556 . . . no
O1 Cu1 N3 C4 -164.9(3) 7_556 . . . no
N1 Cu1 N3 N4 -85.2(3) 7_556 . . . no
N1 Cu1 N3 C4 100.4(3) 7_556 . . . no
Cu1 O1 N5 O2 -71.3(5) . . . . no
Cu1 O1 N5 O3 106.4(5) . . . . no
Cu1 N1 C1 C2 -179.0(3) . . . . no
Cu1 N1 N2 C3 179.0(3) . . . . no
C1 N1 N2 C3 -0.2(4) . . . . no
N2 N1 C1 C2 0.2(4) . . . . no
N1 N2 C3 C2 0.2(5) . . . . no
C4 N3 N4 C6 0.0(4) . . . . no
Cu1 N3 N4 C6 -175.6(3) . . . . no
Cu1 N3 C4 C5 175.2(3) . . . . no
N4 N3 C4 C5 0.0(4) . . . . no
N3 N4 C6 C5 0.0(4) . . . . no
N1 C1 C2 C3 0.0(5) . . . . no
C1 C2 C3 N2 -0.1(5) . . . . no
N3 C4 C5 C6 0.0(5) . . . . no
C4 C5 C6 N4 0.0(5) . . . . no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N2 H2 O3 0.8600 2.1600 2.879(5) 141.00 5_545 yes
N2 H2 O1 0.8600 2.2700 2.834(4) 124.00 7_556 yes
N4 H4 O1 0.8600 2.5900 3.113(4) 120.00 7_556 yes
N4 H4 O2 0.8600 2.1100 2.956(5) 170.00 7_556 yes
C3 H3 O2 0.9300 2.4800 3.292(6) 146.00 6_545 yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#===END
####################################################################### 
# 
# 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_220621f
_audit_block_doi                 10.5517/ccdc.csd.cc2h8756
_database_code_depnum_ccdc_archive 'CCDC 2301817'
loop_
_audit_author_name
_audit_author_address
'lu zujia'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-10-18 deposited with the CCDC.	2024-01-15 downloaded from the CCDC.
;
_audit_creation_date             2023-10-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 Cl6 Cu N8 O8'
_chemical_formula_sum            'C12 H12 Cl6 Cu N8 O8'
_chemical_formula_weight         672.54
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           70
_space_group_name_H-M_alt        'F d d d'
_space_group_name_Hall           '-F 2uv 2vw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/4, -y+1/4, z'
'x, -y+1/4, -z+1/4'
'-x+1/4, y, -z+1/4'
'x, y+1/2, z+1/2'
'-x+1/4, -y+3/4, z+1/2'
'x, -y+3/4, -z+3/4'
'-x+1/4, y+1/2, -z+3/4'
'x+1/2, y, z+1/2'
'-x+3/4, -y+1/4, z+1/2'
'x+1/2, -y+1/4, -z+3/4'
'-x+3/4, y, -z+3/4'
'x+1/2, y+1/2, z'
'-x+3/4, -y+3/4, z'
'x+1/2, -y+3/4, -z+1/4'
'-x+3/4, y+1/2, -z+1/4'
'-x, -y, -z'
'x-1/4, y-1/4, -z'
'-x, y-1/4, z-1/4'
'x-1/4, -y, z-1/4'
'-x, -y+1/2, -z+1/2'
'x-1/4, y+1/4, -z+1/2'
'-x, y+1/4, z+1/4'
'x-1/4, -y+1/2, z+1/4'
'-x+1/2, -y, -z+1/2'
'x+1/4, y-1/4, -z+1/2'
'-x+1/2, y-1/4, z+1/4'
'x+1/4, -y, z+1/4'
'-x+1/2, -y+1/2, -z'
'x+1/4, y+1/4, -z'
'-x+1/2, y+1/4, z-1/4'
'x+1/4, -y+1/2, z-1/4'

_cell_length_a                   36.169(3)
_cell_length_b                   9.9451(9)
_cell_length_c                   13.4069(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4822.5(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1947
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      24.528
_cell_measurement_theta_min      2.253
_shelx_estimated_absorpt_T_max   0.758
_shelx_estimated_absorpt_T_min   0.624
_exptl_absorpt_coefficient_mu    1.627
_exptl_absorpt_correction_T_max  0.7583
_exptl_absorpt_correction_T_min  0.6240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.853
_exptl_crystal_density_meas      1.853
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             2680
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1068
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5437
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.016
_diffrn_reflns_theta_max         25.016
_diffrn_reflns_theta_min         2.252
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                860
_reflns_number_total             1069
_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       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXL 2018/3 (Sheldrick, 2015)'
_refine_diff_density_max         1.092
_refine_diff_density_min         -1.032
_refine_diff_density_rms         0.162
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     99
_refine_ls_number_reflns         1069
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0930
_refine_ls_restrained_S_all      1.233
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1255P)²+101.8730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2395
_refine_ls_wR_factor_ref         0.2527
_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
2. Restrained distances
 Cl2-O1 = Cl2-O3 = Cl2-O2 = Cl2-O4
 1.4 with sigma of 0.01
 O1-O2 \\sim O1-O3 \\sim O1-O4 \\sim O2-O3 \\sim O2-O4 \\sim O3-O4
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Cl2 \\sim O1 \\sim O2 \\sim O3 \\sim O4: within 2A with sigma of 0.02 and sigma
for terminal atoms of 0.04 within 2A
4. Others
 Fixed Sof: O1(0.5) O2(0.5) O3(0.5) O4(0.5)
5.a Riding coordinates:
 N2(H2)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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_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
Cu1 Cu 0.125000 0.625000 0.125000 0.0369(6) Uani 1 4 d S T P . .
Cl1 Cl 0.00510(8) 0.2749(3) 0.0246(3) 0.1025(13) Uani 1 1 d . . . . .
Cl2 Cl 0.125000 0.625000 0.3924(2) 0.0841(13) Uani 1 2 d DS TU P . .
N1 N 0.08650(16) 0.4836(6) 0.1236(5) 0.0420(15) Uani 1 1 d . . . . .
N2 N 0.0847(2) 0.3853(6) 0.1894(5) 0.0524(18) Uani 1 1 d . . . . .
H2 H 0.099747 0.376541 0.238710 0.063 Uiso 1 1 d R U . . .
O1 O 0.1341(5) 0.5857(16) 0.2984(6) 0.112(6) Uani 0.5 1 d D U P A -1
O2 O 0.0855(2) 0.609(2) 0.4025(12) 0.144(9) Uani 0.5 1 d D U P A -1
O3 O 0.1292(6) 0.7712(9) 0.3940(11) 0.139(8) Uani 0.5 1 d D U P A -1
O4 O 0.1426(4) 0.5705(14) 0.4675(8) 0.120(7) Uani 0.5 1 d D U P A -1
C1 C 0.0596(2) 0.4592(8) 0.0587(6) 0.051(2) Uani 1 1 d . . . . .
H1 H 0.054376 0.511424 0.002918 0.061 Uiso 1 1 calc R U . . .
C2 C 0.0410(2) 0.3462(7) 0.0861(7) 0.050(2) Uani 1 1 d . . . . .
C3 C 0.0570(2) 0.3016(8) 0.1699(8) 0.059(2) Uani 1 1 d . . . . .
H3 H 0.050127 0.226718 0.207074 0.071 Uiso 1 1 calc R 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
Cu1 N1 1.979(6) 2_565 ?
Cu1 N1 1.979(6) 3_565 ?
Cu1 N1 1.979(6) 4 ?
Cu1 N1 1.979(6) . ?
Cu1 O1 2.381(10) . ?
Cl1 C2 1.693(8) . ?
Cl2 O1 1.360(8) . ?
Cl2 O2 1.444(8) . ?
Cl2 O3 1.463(8) . ?
Cl2 O4 1.309(8) . ?
N1 N2 1.318(9) . ?
N1 C1 1.326(10) . ?
N2 H2 0.8602 . ?
N2 C3 1.329(10) . ?
C1 H1 0.9300 . ?
C1 C2 1.363(11) . ?
C2 C3 1.339(13) . ?
C3 H3 0.9300 . ?

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
N1 Cu1 N1 90.6(3) 2_565 4 ?
N1 Cu1 N1 89.4(3) 4 . ?
N1 Cu1 N1 178.9(4) 2_565 . ?
N1 Cu1 N1 89.4(3) 2_565 3_565 ?
N1 Cu1 N1 178.9(4) 4 3_565 ?
N1 Cu1 N1 90.6(3) 3_565 . ?
N1 Cu1 O1 91.6(5) 2_565 . ?
N1 Cu1 O1 89.4(5) . . ?
N1 Cu1 O1 77.1(4) 4 . ?
N1 Cu1 O1 101.9(4) 3_565 . ?
O1 Cl2 O2 107.2(6) . . ?
O1 Cl2 O3 105.9(6) . . ?
O2 Cl2 O3 102.2(6) . . ?
O4 Cl2 O1 118.4(7) . . ?
O4 Cl2 O2 111.3(6) . . ?
O4 Cl2 O3 110.4(6) . . ?
N2 N1 Cu1 123.7(5) . . ?
N2 N1 C1 105.6(6) . . ?
C1 N1 Cu1 130.6(5) . . ?
N1 N2 H2 124.0 . . ?
N1 N2 C3 111.7(7) . . ?
C3 N2 H2 124.3 . . ?
Cl2 O1 Cu1 145.4(9) . . ?
N1 C1 H1 125.2 . . ?
N1 C1 C2 109.7(7) . . ?
C2 C1 H1 125.2 . . ?
C1 C2 Cl1 126.4(7) . . ?
C3 C2 Cl1 127.0(7) . . ?
C3 C2 C1 106.5(7) . . ?
N2 C3 C2 106.5(8) . . ?
N2 C3 H3 126.7 . . ?
C2 C3 H3 126.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 N1 N2 C3 -178.0(6) . . . . ?
Cu1 N1 C1 C2 176.9(6) . . . . ?
Cl1 C2 C3 N2 177.7(7) . . . . ?
N1 N2 C3 C2 1.8(10) . . . . ?
N1 C1 C2 Cl1 -178.7(7) . . . . ?
N1 C1 C2 C3 0.1(10) . . . . ?
N2 N1 C1 C2 1.0(9) . . . . ?
O2 Cl2 O1 Cu1 60(2) . . . . ?
O3 Cl2 O1 Cu1 -49(2) . . . . ?
O4 Cl2 O1 Cu1 -173.2(16) . . . . ?
C1 N1 N2 C3 -1.8(10) . . . . ?
C1 C2 C3 N2 -1.1(10) . . . . ?


_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_220703g
_audit_block_doi                 10.5517/ccdc.csd.cc2h8767
_database_code_depnum_ccdc_archive 'CCDC 2301818'
loop_
_audit_author_name
_audit_author_address
'lu zujia'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-10-18 deposited with the CCDC.	2024-01-15 downloaded from the CCDC.
;
_audit_creation_date             2022-07-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C27 H33 Cu3 N18 O1, N1 O3'
_chemical_formula_sum            'C27 H33 Cu3 N19 O4'
_chemical_formula_weight         878.34
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-y, x-y, z'
3 '-x+y, -x, z'
4 'x+2/3, y+1/3, z+1/3'
5 '-y+2/3, x-y+1/3, z+1/3'
6 '-x+y+2/3, -x+1/3, z+1/3'
7 'x+1/3, y+2/3, z+2/3'
8 '-y+1/3, x-y+2/3, z+2/3'
9 '-x+y+1/3, -x+2/3, z+2/3'
10 '-x, -y, -z'
11 'y, -x+y, -z'
12 'x-y, x, -z'
13 '-x+2/3, -y+1/3, -z+1/3'
14 'y+2/3, -x+y+1/3, -z+1/3'
15 'x-y+2/3, x+1/3, -z+1/3'
16 '-x+1/3, -y+2/3, -z+2/3'
17 'y+1/3, -x+y+2/3, -z+2/3'
18 'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   12.1710(13)
_cell_length_b                   12.1710(13)
_cell_length_c                   43.960(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     5639.5(10)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    3734
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.175
_cell_measurement_theta_min      2.675
_exptl_absorpt_coefficient_mu    1.742
_exptl_absorpt_correction_T_max  0.7925
_exptl_absorpt_correction_T_min  0.6056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_meas      1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2682
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            9447
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.99
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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                1712
_reflns_number_total             2223
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         1.461
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0560
_refine_ls_restrained_S_all      1.117
_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)+(0.1062P)²+0.7254P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1606
_refine_ls_wR_factor_ref         0.1678
_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
2.a Aromatic/amide H refined with riding coordinates:
 N4(H4), N6(H6), C1(H1), C2(H2), C3(H3), C4(H4a), C5(H5), C6(H6a), C7(H7),
 C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu1 Cu 0.12654(5) 0.17828(5) 0.073440(14) 0.0415(3) Uani 1 d . . 1 . . .
N1 N -0.0088(4) 0.2182(3) 0.07455(9) 0.0411(9) Uani 1 d . . 1 . . .
N2 N -0.1305(3) 0.1259(4) 0.07241(10) 0.0443(10) Uani 1 d . . 1 . . .
N3 N 0.1927(5) 0.2536(4) 0.12408(10) 0.0580(12) Uani 1 d . . 1 . . .
N4 N 0.1764(5) 0.3343(4) 0.14128(11) 0.0595(12) Uani 1 d . . 1 . . .
H4 H 0.1716 0.3977 0.1342 0.071 Uiso 1 calc . . 1 R . .
N5 N 0.2387(4) 0.3352(4) 0.04898(9) 0.0472(10) Uani 1 d . . 1 . . .
N6 N 0.2407(4) 0.3313(5) 0.01890(11) 0.0634(12) Uani 1 d . . 1 . . .
H6 H 0.1923 0.2653 0.0082 0.076 Uiso 1 calc . . 1 R . .
N7 N 0.3333 0.6667 0.11881(15) 0.0402(15) Uani 1 d . . 3 S T P
O1 O 0.0000 0.0000 0.08626(12) 0.0352(11) Uani 1 d . . 3 S T P
O2 O 0.2210(3) 0.5827(3) 0.11824(10) 0.0658(11) Uani 1 d . . 1 . . .
C1 C -0.0061(6) 0.3279(5) 0.07725(13) 0.0564(14) Uani 1 d . . 1 . . .
H1 H 0.0671 0.4067 0.0789 0.068 Uiso 1 calc . . 1 R . .
C2 C -0.1286(6) 0.3076(6) 0.07718(15) 0.0688(17) Uani 1 d . . 1 . . .
H2A H -0.1546 0.3675 0.0787 0.083 Uiso 1 calc . . 1 R . .
C3 C -0.2013(6) 0.1807(5) 0.07442(16) 0.0666(17) Uani 1 d . . 1 . . .
H3 H -0.2895 0.1370 0.0740 0.080 Uiso 1 calc . . 1 R . .
C4 C 0.1974(6) 0.1760(6) 0.14362(13) 0.0641(16) Uani 1 d . . 1 . . .
H4A H 0.2108 0.1095 0.1384 0.077 Uiso 1 calc . . 1 R . .
C5 C 0.1808(7) 0.2029(7) 0.17241(15) 0.0779(19) Uani 1 d . . 1 . . .
H5 H 0.1783 0.1596 0.1901 0.094 Uiso 1 calc . . 1 R . .
C6 C 0.1687(7) 0.3063(6) 0.16990(14) 0.0738(18) Uani 1 d . . 1 . . .
H6A H 0.1569 0.3498 0.1858 0.089 Uiso 1 calc . . 1 R . .
C7 C 0.3259(5) 0.4514(5) 0.05617(14) 0.0566(14) Uani 1 d . . 1 . . .
H7 H 0.3465 0.4828 0.0759 0.068 Uiso 1 calc . . 1 R . .
C8 C 0.3814(6) 0.5184(6) 0.0307(2) 0.079(2) Uani 1 d . . 1 . . .
H8 H 0.4460 0.6025 0.0295 0.095 Uiso 1 calc . . 1 R . .
C9 C 0.3239(7) 0.4383(7) 0.00759(18) 0.083(2) Uani 1 d . . 1 . . .
H9 H 0.3411 0.4568 -0.0130 0.100 Uiso 1 calc . . 1 R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.938(4) . ?
Cu1 N2 1.939(4) 3 ?
Cu1 N3 2.389(4) . ?
Cu1 N5 2.015(4) . ?
Cu1 O1 2.0139(15) . ?
N1 N2 1.342(5) . ?
N1 C1 1.324(6) . ?
N2 Cu1 1.939(4) 2 ?
N2 C3 1.329(6) . ?
N3 N4 1.331(6) . ?
N3 C4 1.299(7) . ?
N4 H4 0.8600 . ?
N4 C6 1.294(8) . ?
N5 N6 1.324(6) . ?
N5 C7 1.314(6) . ?
N6 H6 0.8600 . ?
N6 C9 1.284(8) . ?
N7 O2 1.232(4) 2_665 ?
N7 O2 1.232(4) 3_565 ?
N7 O2 1.232(4) . ?
O1 Cu1 2.0139(15) 2 ?
O1 Cu1 2.0139(15) 3 ?
C1 H1 0.9300 . ?
C1 C2 1.384(8) . ?
C2 H2A 0.9300 . ?
C2 C3 1.349(8) . ?
C3 H3 0.9300 . ?
C4 H4A 0.9300 . ?
C4 C5 1.348(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.343(9) . ?
C6 H6A 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.349(9) . ?
C8 H8 0.9300 . ?
C8 C9 1.339(10) . ?
C9 H9 0.9300 . ?

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
N1 Cu1 N2 177.51(15) . 3 ?
N1 Cu1 N3 92.64(16) . . ?
N1 Cu1 N5 91.93(16) . . ?
N1 Cu1 O1 88.58(10) . . ?
N2 Cu1 N3 88.16(16) 3 . ?
N2 Cu1 N5 90.23(16) 3 . ?
N2 Cu1 O1 89.00(11) 3 . ?
N5 Cu1 N3 101.25(17) . . ?
O1 Cu1 N3 94.71(18) . . ?
O1 Cu1 N5 163.98(18) . . ?
N2 N1 Cu1 120.6(3) . . ?
C1 N1 Cu1 131.3(3) . . ?
C1 N1 N2 108.1(4) . . ?
N1 N2 Cu1 121.5(3) . 2 ?
C3 N2 Cu1 130.5(4) . 2 ?
C3 N2 N1 107.2(4) . . ?
N4 N3 Cu1 131.8(3) . . ?
C4 N3 Cu1 117.8(4) . . ?
C4 N3 N4 103.8(4) . . ?
N3 N4 H4 124.0 . . ?
C6 N4 N3 112.1(5) . . ?
C6 N4 H4 124.0 . . ?
N6 N5 Cu1 121.0(3) . . ?
C7 N5 Cu1 133.8(4) . . ?
C7 N5 N6 105.0(4) . . ?
N5 N6 H6 124.1 . . ?
C9 N6 N5 111.7(5) . . ?
C9 N6 H6 124.1 . . ?
O2 N7 O2 119.96(3) 3_565 . ?
O2 N7 O2 119.96(3) 3_565 2_665 ?
O2 N7 O2 119.96(3) . 2_665 ?
Cu1 O1 Cu1 112.50(12) 2 . ?
Cu1 O1 Cu1 112.50(12) . 3 ?
Cu1 O1 Cu1 112.50(12) 2 3 ?
N1 C1 H1 125.1 . . ?
N1 C1 C2 109.8(5) . . ?
C2 C1 H1 125.1 . . ?
C1 C2 H2A 128.2 . . ?
C3 C2 C1 103.6(5) . . ?
C3 C2 H2A 128.2 . . ?
N2 C3 C2 111.2(5) . . ?
N2 C3 H3 124.4 . . ?
C2 C3 H3 124.4 . . ?
N3 C4 H4A 123.9 . . ?
N3 C4 C5 112.2(5) . . ?
C5 C4 H4A 123.9 . . ?
C4 C5 H5 127.7 . . ?
C6 C5 C4 104.6(6) . . ?
C6 C5 H5 127.7 . . ?
N4 C6 C5 107.4(6) . . ?
N4 C6 H6A 126.3 . . ?
C5 C6 H6A 126.3 . . ?
N5 C7 H7 125.0 . . ?
N5 C7 C8 110.0(6) . . ?
C8 C7 H7 125.0 . . ?
C7 C8 H8 127.2 . . ?
C9 C8 C7 105.6(6) . . ?
C9 C8 H8 127.2 . . ?
N6 C9 C8 107.7(6) . . ?
N6 C9 H9 126.2 . . ?
C8 C9 H9 126.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 N1 N2 Cu1 8.1(5) . . . 2 ?
Cu1 N1 N2 C3 178.8(4) . . . . ?
Cu1 N1 C1 C2 -179.4(4) . . . . ?
Cu1 N2 C3 C2 170.9(4) 2 . . . ?
Cu1 N3 N4 C6 148.3(5) . . . . ?
Cu1 N3 C4 C5 -153.0(4) . . . . ?
Cu1 N5 N6 C9 -175.7(4) . . . . ?
Cu1 N5 C7 C8 174.7(4) . . . . ?
N1 Cu1 N3 N4 -22.2(5) . . . . ?
N1 Cu1 N3 C4 124.2(5) . . . . ?
N1 Cu1 N5 N6 -93.3(4) . . . . ?
N1 Cu1 N5 C7 92.5(5) . . . . ?
N1 Cu1 O1 Cu1 26.9(2) . . . 2 ?
N1 Cu1 O1 Cu1 155.2(2) . . . 3 ?
N1 N2 C3 C2 1.3(7) . . . . ?
N1 C1 C2 C3 0.2(8) . . . . ?
N2 Cu1 N1 N2 -8(4) 3 . . . ?
N2 Cu1 N1 C1 172(20) 3 . . . ?
N2 Cu1 N3 N4 160.2(5) 3 . . . ?
N2 Cu1 N3 C4 -53.4(5) 3 . . . ?
N2 Cu1 N5 N6 85.4(4) 3 . . . ?
N2 Cu1 N5 C7 -88.7(5) 3 . . . ?
N2 Cu1 O1 Cu1 -152.5(2) 3 . . 2 ?
N2 Cu1 O1 Cu1 -24.2(2) 3 . . 3 ?
N2 N1 C1 C2 0.6(7) . . . . ?
N3 Cu1 N1 N2 -116.4(4) . . . . ?
N3 Cu1 N1 C1 63.5(5) . . . . ?
N3 Cu1 N5 N6 173.6(4) . . . . ?
N3 Cu1 N5 C7 -0.6(5) . . . . ?
N3 Cu1 O1 Cu1 119.5(2) . . . 2 ?
N3 Cu1 O1 Cu1 -112.2(2) . . . 3 ?
N3 N4 C6 C5 0.3(8) . . . . ?
N3 C4 C5 C6 -1.7(8) . . . . ?
N4 N3 C4 C5 1.9(7) . . . . ?
N5 Cu1 N1 N2 142.2(4) . . . . ?
N5 Cu1 N1 C1 -37.8(5) . . . . ?
N5 Cu1 N3 N4 70.3(5) . . . . ?
N5 Cu1 N3 C4 -143.3(5) . . . . ?
N5 Cu1 O1 Cu1 -65.1(5) . . . 2 ?
N5 Cu1 O1 Cu1 63.2(5) . . . 3 ?
N5 N6 C9 C8 0.2(8) . . . . ?
N5 C7 C8 C9 0.3(7) . . . . ?
N6 N5 C7 C8 -0.1(6) . . . . ?
O1 Cu1 N1 N2 -21.8(4) . . . . ?
O1 Cu1 N1 C1 158.2(5) . . . . ?
O1 Cu1 N3 N4 -111.0(5) . . . . ?
O1 Cu1 N3 C4 35.4(5) . . . . ?
O1 Cu1 N5 N6 -1.8(7) . . . . ?
O1 Cu1 N5 C7 -175.9(3) . . . . ?
C1 N1 N2 Cu1 -171.8(4) . . . 2 ?
C1 N1 N2 C3 -1.1(6) . . . . ?
C1 C2 C3 N2 -1.0(8) . . . . ?
C4 N3 N4 C6 -1.4(7) . . . . ?
C4 C5 C6 N4 0.8(8) . . . . ?
C7 N5 N6 C9 -0.1(7) . . . . ?
C7 C8 C9 N6 -0.3(8) . . . . ?


_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_220703f
_audit_block_doi                 10.5517/ccdc.csd.cc2h8734
_database_code_depnum_ccdc_archive 'CCDC 2301815'
loop_
_audit_author_name
_audit_author_address
'lu zujia'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-10-18 deposited with the CCDC.	2024-01-15 downloaded from the CCDC.
;
_audit_creation_date             2023-10-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 Cl4 Cu N8, 2(N O3)'
_chemical_formula_sum            'C12 H12 Cl4 Cu N10 O6'
_chemical_formula_weight         597.66
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   38.031(3)
_cell_length_b                   7.9094(8)
_cell_length_c                   14.7249(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.767(3)
_cell_angle_gamma                90
_cell_volume                     4319.8(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3735
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.228
_cell_measurement_theta_min      2.197
_shelx_estimated_absorpt_T_max   0.823
_shelx_estimated_absorpt_T_min   0.678
_exptl_absorpt_coefficient_mu    1.561
_exptl_absorpt_correction_T_max  0.8228
_exptl_absorpt_correction_T_min  0.6779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.838
_exptl_crystal_density_meas      1.838
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             2392
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10045
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.018
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_min         2.196
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3015
_reflns_number_total             3800
_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       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         1.554
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         3800
_refine_ls_number_restraints     173
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0759
_refine_ls_restrained_S_all      1.128
_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)+(0.0522P)²+63.8785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1873
_refine_ls_wR_factor_ref         0.1943
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 O1-O2' = O2'-O3' = O3'-O1 = O4'-O5' = O5'-O6 = O6-O4'
 2.15 with sigma of 0.02
 N9-O2' = N9-O3' = N10-O4' = N10-O5
 1.21 with sigma of 0.01
3. Restrained planarity
 N10, O4', O5', O6
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
O1 \\sim O2 \\sim O3 \\sim O4 \\sim O5 \\sim O6 \\sim O2' \\sim O3' \\sim O4'
\\sim O5': within 3.8A with sigma of 0.02 and sigma for terminal atoms of 0.04
within 3.8A
5. Others
 Sof(O2')=Sof(O3')=1-FVAR(1)
 Sof(O2)=Sof(O3)=FVAR(1)
 Sof(O4')=Sof(O5')=1-FVAR(2)
 Sof(O4)=Sof(O5)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4), N6(H6), N8(H8), C1(H1), C3(H3), C4(H4A), C6(H6A), C7(H7),
 C9(H9), C10(H10), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.37862(2) 0.75934(11) 0.43428(6) 0.0369(3) Uani 1 1 d . . . . .
Cl1 Cl 0.49315(6) 1.1998(3) 0.61780(17) 0.0664(7) Uani 1 1 d . . . . .
Cl2 Cl 0.26149(6) 0.8857(3) 0.6134(2) 0.0706(7) Uani 1 1 d . . . . .
Cl3 Cl 0.48974(7) 0.3054(3) 0.37295(18) 0.0718(7) Uani 1 1 d . . . . .
Cl4 Cl 0.25174(7) 0.6461(4) 0.1456(2) 0.0829(9) Uani 1 1 d . . . . .
N1 N 0.41649(16) 0.8833(8) 0.5254(4) 0.0370(14) Uani 1 1 d . . . . .
N2 N 0.41740(16) 0.8873(8) 0.6163(4) 0.0425(15) Uani 1 1 d . . . . .
H2 H 0.403064 0.830337 0.642333 0.051 Uiso 1 1 calc R U . . .
N3 N 0.34129(15) 0.8639(8) 0.4912(4) 0.0370(14) Uani 1 1 d . . . . .
N4 N 0.33958(18) 1.0272(8) 0.5107(5) 0.0501(18) Uani 1 1 d . . . . .
H4 H 0.354070 1.101984 0.497380 0.060 Uiso 1 1 calc R U . . .
N5 N 0.41536(16) 0.6324(8) 0.3826(4) 0.0379(14) Uani 1 1 d . . . . .
N6 N 0.41583(16) 0.6278(8) 0.2917(4) 0.0430(15) Uani 1 1 d . . . . .
H6 H 0.401755 0.686529 0.249610 0.052 Uiso 1 1 calc R U . . .
N7 N 0.33948(17) 0.6626(8) 0.3359(4) 0.0395(14) Uani 1 1 d . . . . .
N8 N 0.33748(18) 0.5002(8) 0.3107(5) 0.0477(16) Uani 1 1 d . . . . .
H8 H 0.353047 0.424722 0.334748 0.057 Uiso 1 1 calc R U . . .
N9 N 0.37624(19) 0.1159(9) 0.3066(5) 0.056(2) Uani 1 1 d D . . . .
N10 N 0.37435(19) 0.4137(10) 0.5581(5) 0.063(2) Uani 1 1 d D . . . .
O1 O 0.3781(2) 0.2126(8) 0.2435(5) 0.078(2) Uani 1 1 d D U . . .
O2 O 0.3857(5) -0.0283(17) 0.3116(15) 0.047(4) Uani 0.671(14) 1 d . U P A 1
O3 O 0.3736(3) 0.2035(12) 0.3796(6) 0.063(3) Uani 0.671(14) 1 d . U P A 1
O4 O 0.3835(3) 0.2998(10) 0.6101(6) 0.073(3) Uani 0.747(12) 1 d . U P B 1
O5 O 0.3424(2) 0.4189(11) 0.5107(7) 0.074(3) Uani 0.747(12) 1 d D U P B 1
O6 O 0.38929(17) 0.5520(7) 0.5616(4) 0.0587(16) Uani 1 1 d D U . . .
O2' O 0.3936(11) -0.016(4) 0.315(4) 0.064(10) Uani 0.329(14) 1 d D U P A 2
O3' O 0.3451(4) 0.107(2) 0.3225(14) 0.062(6) Uani 0.329(14) 1 d D U P A 2
O4' O 0.3743(6) 0.321(2) 0.4876(11) 0.055(6) Uani 0.253(12) 1 d D U P B 2
O5' O 0.3605(7) 0.356(3) 0.6181(15) 0.100(9) Uani 0.253(12) 1 d D U P B 2
C1 C 0.44234(19) 0.9876(9) 0.5139(5) 0.0380(17) Uani 1 1 d . . . . .
H1 H 0.448375 1.011048 0.457368 0.046 Uiso 1 1 calc R U . . .
C2 C 0.4587(2) 1.0551(9) 0.5971(5) 0.0384(17) Uani 1 1 d . . . . .
C3 C 0.4427(2) 0.9881(10) 0.6616(5) 0.0451(19) Uani 1 1 d . . . . .
H3 H 0.448356 1.009050 0.725348 0.054 Uiso 1 1 calc R U . . .
C4 C 0.3151(2) 0.7940(10) 0.5236(6) 0.0463(19) Uani 1 1 d . . . . .
H4A H 0.309512 0.679412 0.519974 0.056 Uiso 1 1 calc R U . . .
C5 C 0.29720(19) 0.9144(10) 0.5634(6) 0.0426(18) Uani 1 1 d . . . . .
C6 C 0.3133(2) 1.0621(10) 0.5526(6) 0.049(2) Uani 1 1 d . . . . .
H6A H 0.307053 1.168274 0.571119 0.059 Uiso 1 1 calc R U . . .
C7 C 0.4403(2) 0.5251(10) 0.4221(5) 0.0408(17) Uani 1 1 d . . . . .
H7 H 0.446414 0.501120 0.485468 0.049 Uiso 1 1 calc R U . . .
C8 C 0.4562(2) 0.4529(9) 0.3560(5) 0.0386(17) Uani 1 1 d . . . . .
C9 C 0.4404(2) 0.5229(10) 0.2749(5) 0.0443(18) Uani 1 1 d . . . . .
H9 H 0.445763 0.501429 0.217330 0.053 Uiso 1 1 calc R U . . .
C10 C 0.3108(2) 0.7337(10) 0.2837(6) 0.0475(19) Uani 1 1 d . . . . .
H10 H 0.304813 0.847450 0.285816 0.057 Uiso 1 1 calc R U . . .
C11 C 0.2908(2) 0.6167(11) 0.2258(6) 0.0459(19) Uani 1 1 d . . . . .
C12 C 0.3089(2) 0.4701(12) 0.2448(6) 0.057(2) Uani 1 1 d . . . . .
H12 H 0.302320 0.366334 0.216367 0.068 Uiso 1 1 calc R 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
Cu1 N1 1.995(6) . ?
Cu1 N3 1.982(6) . ?
Cu1 N5 2.002(6) . ?
Cu1 N7 1.987(6) . ?
Cl1 C2 1.716(7) . ?
Cl2 C5 1.697(7) . ?
Cl3 C8 1.707(7) . ?
Cl4 C11 1.698(8) . ?
N1 N2 1.332(8) . ?
N1 C1 1.323(9) . ?
N2 H2 0.8600 . ?
N2 C3 1.312(9) . ?
N3 N4 1.328(8) . ?
N3 C4 1.317(9) . ?
N4 H4 0.8600 . ?
N4 C6 1.314(10) . ?
N5 N6 1.343(8) . ?
N5 C7 1.309(9) . ?
N6 H6 0.8600 . ?
N6 C9 1.314(10) . ?
N7 N8 1.334(9) . ?
N7 C10 1.315(10) . ?
N8 H8 0.8600 . ?
N8 C12 1.309(10) . ?
N9 O1 1.218(9) . ?
N9 O2 1.192(14) . ?
N9 O3 1.301(11) . ?
N9 O2' 1.226(10) . ?
N9 O3' 1.258(9) . ?
N10 O4 1.184(10) . ?
N10 O5 1.262(8) . ?
N10 O6 1.229(8) . ?
N10 O4' 1.270(9) . ?
N10 O5' 1.214(18) . ?
C1 H1 0.9300 . ?
C1 C2 1.354(10) . ?
C2 C3 1.345(10) . ?
C3 H3 0.9300 . ?
C4 H4A 0.9300 . ?
C4 C5 1.375(11) . ?
C5 C6 1.344(11) . ?
C6 H6A 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.377(10) . ?
C8 C9 1.333(11) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.368(11) . ?
C11 C12 1.346(12) . ?
C12 H12 0.9300 . ?

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
N1 Cu1 N5 92.4(2) . . ?
N3 Cu1 N1 89.3(2) . . ?
N3 Cu1 N5 174.4(3) . . ?
N3 Cu1 N7 88.7(2) . . ?
N7 Cu1 N1 173.1(3) . . ?
N7 Cu1 N5 90.2(2) . . ?
N2 N1 Cu1 122.8(5) . . ?
C1 N1 Cu1 131.8(5) . . ?
C1 N1 N2 105.0(6) . . ?
N1 N2 H2 123.9 . . ?
C3 N2 N1 112.3(6) . . ?
C3 N2 H2 123.9 . . ?
N4 N3 Cu1 124.8(5) . . ?
C4 N3 Cu1 130.3(5) . . ?
C4 N3 N4 104.7(6) . . ?
N3 N4 H4 123.7 . . ?
C6 N4 N3 112.6(6) . . ?
C6 N4 H4 123.7 . . ?
N6 N5 Cu1 123.8(5) . . ?
C7 N5 Cu1 130.9(5) . . ?
C7 N5 N6 104.9(6) . . ?
N5 N6 H6 124.1 . . ?
C9 N6 N5 111.8(6) . . ?
C9 N6 H6 124.1 . . ?
N8 N7 Cu1 124.1(5) . . ?
C10 N7 Cu1 130.8(5) . . ?
C10 N7 N8 105.1(6) . . ?
N7 N8 H8 124.2 . . ?
C12 N8 N7 111.6(7) . . ?
C12 N8 H8 124.2 . . ?
O1 N9 O3 108.9(7) . . ?
O1 N9 O2' 119.5(18) . . ?
O1 N9 O3' 113.1(10) . . ?
O2 N9 O1 125.5(11) . . ?
O2 N9 O3 122.3(12) . . ?
O2' N9 O3' 116.2(16) . . ?
O4 N10 O5 119.4(9) . . ?
O4 N10 O6 125.7(7) . . ?
O6 N10 O5 112.0(8) . . ?
O6 N10 O4' 117.8(10) . . ?
O5' N10 O6 125.1(13) . . ?
O5' N10 O4' 117.1(14) . . ?
N1 C1 H1 125.2 . . ?
N1 C1 C2 109.6(6) . . ?
C2 C1 H1 125.2 . . ?
C1 C2 Cl1 127.1(6) . . ?
C3 C2 Cl1 125.7(6) . . ?
C3 C2 C1 107.2(6) . . ?
N2 C3 C2 105.9(6) . . ?
N2 C3 H3 127.0 . . ?
C2 C3 H3 127.0 . . ?
N3 C4 H4A 124.8 . . ?
N3 C4 C5 110.4(7) . . ?
C5 C4 H4A 124.8 . . ?
C4 C5 Cl2 127.7(6) . . ?
C6 C5 Cl2 126.6(6) . . ?
C6 C5 C4 105.7(7) . . ?
N4 C6 C5 106.7(7) . . ?
N4 C6 H6A 126.7 . . ?
C5 C6 H6A 126.7 . . ?
N5 C7 H7 125.0 . . ?
N5 C7 C8 110.0(7) . . ?
C8 C7 H7 125.0 . . ?
C7 C8 Cl3 127.6(6) . . ?
C9 C8 Cl3 126.0(6) . . ?
C9 C8 C7 106.3(7) . . ?
N6 C9 C8 106.9(7) . . ?
N6 C9 H9 126.5 . . ?
C8 C9 H9 126.5 . . ?
N7 C10 H10 124.8 . . ?
N7 C10 C11 110.4(7) . . ?
C11 C10 H10 124.8 . . ?
C10 C11 Cl4 128.3(7) . . ?
C12 C11 Cl4 126.3(6) . . ?
C12 C11 C10 105.4(7) . . ?
N8 C12 C11 107.4(7) . . ?
N8 C12 H12 126.3 . . ?
C11 C12 H12 126.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 N1 N2 C3 -174.4(5) . . . . ?
Cu1 N1 C1 C2 172.9(5) . . . . ?
Cu1 N3 N4 C6 -176.7(6) . . . . ?
Cu1 N3 C4 C5 175.5(5) . . . . ?
Cu1 N5 N6 C9 -173.8(5) . . . . ?
Cu1 N5 C7 C8 172.1(5) . . . . ?
Cu1 N7 N8 C12 179.6(6) . . . . ?
Cu1 N7 C10 C11 -179.1(5) . . . . ?
Cl1 C2 C3 N2 178.6(6) . . . . ?
Cl2 C5 C6 N4 -179.9(6) . . . . ?
Cl3 C8 C9 N6 179.3(6) . . . . ?
Cl4 C11 C12 N8 -179.8(6) . . . . ?
N1 N2 C3 C2 0.9(10) . . . . ?
N1 C1 C2 Cl1 -178.8(6) . . . . ?
N1 C1 C2 C3 0.9(9) . . . . ?
N2 N1 C1 C2 -0.3(9) . . . . ?
N3 N4 C6 C5 1.4(10) . . . . ?
N3 C4 C5 Cl2 179.5(6) . . . . ?
N3 C4 C5 C6 1.0(10) . . . . ?
N4 N3 C4 C5 -0.1(9) . . . . ?
N5 N6 C9 C8 1.3(9) . . . . ?
N5 C7 C8 Cl3 -179.6(6) . . . . ?
N5 C7 C8 C9 1.2(9) . . . . ?
N6 N5 C7 C8 -0.4(8) . . . . ?
N7 N8 C12 C11 -0.7(10) . . . . ?
N7 C10 C11 Cl4 -179.9(6) . . . . ?
N7 C10 C11 C12 -0.3(10) . . . . ?
N8 N7 C10 C11 -0.1(9) . . . . ?
C1 N1 N2 C3 -0.4(9) . . . . ?
C1 C2 C3 N2 -1.1(9) . . . . ?
C4 N3 N4 C6 -0.8(10) . . . . ?
C4 C5 C6 N4 -1.4(10) . . . . ?
C7 N5 N6 C9 -0.6(9) . . . . ?
C7 C8 C9 N6 -1.5(9) . . . . ?
C10 N7 N8 C12 0.5(9) . . . . ?
C10 C11 C12 N8 0.6(10) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
