# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2041819'
loop_
_audit_author_name
_audit_author_address
'Marta Pockaj'
;University of Ljubljana, Faculty of Chemistry and Chemical Technology
Slovenia
;
_audit_update_record             
;
2020-11-01 deposited with the CCDC.	2021-01-18 downloaded from the CCDC.
;

_vrf_PLAT241_shelx               
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of        O23 Check
RESPONSE: O23 is the terminal oxygen atom of coordinated nitrate anion, and as such its Ueq is slightly higher than these of adjacent atoms. The correct atom type is assigned.
;
_vrf_PLAT430_shelx               
;
PROBLEM: Short Inter D...A Contact  O15      ..O18      .       2.89 Ang.
RESPONSE: O18 is an acceptor of C-H...O hydrogen bond, donated by OMe group (=methyl group bound to O15).
;
_vrf_PLAT934_shelx               
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check
RESPONSE: O-H bondlengths (O29-H29A, O29-H29b, O50w-h50A, O50w-H50b) were restrained to 0.85(2) A to obtain realistic distances.
;
# Added during the CSD deposition process: Sunday 01 November 2020 05:27 PM
# end Validation Reply Form


_vrf_PLAT002_shelx               
;
RESPONSE:
O-H bondlengths (O29-H29A, O29-H29b, O50w-h50A, O50w-H50b) 
were restrained to 0.85(2) A to obtain realistic distances.
;

_vrf_PLAT172_shelx               
;
RESPONSE:
O-H bondlengths (O29-H29A, O29-H29b, O50w-h50A, O50w-H50b) 
were restrained to 0.85(2) A to obtain realistic distances.
;

_vrf_PLAT860_shelx               
;
RESPONSE:
O-H bondlengths (O29-H29A, O29-H29b, O50w-h50A, O50w-H50b) 
were restrained to 0.85(2) A to obtain realistic distances.
;



_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 Cu N4 O11, H2 O'
_chemical_formula_sum            'C14 H16 Cu N4 O12'
_chemical_formula_weight         495.85

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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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.
;

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'

_cell_length_a                   10.3255(6)
_cell_length_b                   22.7235(11)
_cell_length_c                   8.0546(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.849(6)
_cell_angle_gamma                90
_cell_volume                     1849.59(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2273
_cell_measurement_theta_min      3.5670
_cell_measurement_theta_max      29.7420

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_F_000             1012
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.259
_shelx_estimated_absorpt_T_min   0.704
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_T_min  0.87163
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.4933
_diffrn_reflns_number            5050
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.067
_diffrn_reflns_theta_max         30.293
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.591
_diffrn_reflns_point_group_measured_fraction_full 0.726
_reflns_number_total             3279
_reflns_number_gt                3022
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.330
_reflns_Friedel_fraction_max     0.294
_reflns_Friedel_fraction_full    0.451

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0329P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 748 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3279
_refine_ls_number_parameters     298
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0745
_refine_ls_wR_factor_gt          0.0714
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.65311(4) 0.15477(2) 0.54286(5) 0.01722(12) Uani 1 1 d . . . . .
N1 N 0.7795(3) 0.10149(14) 0.4611(4) 0.0160(7) Uani 1 1 d . . . . .
C2 C 0.7583(4) 0.04336(17) 0.4785(5) 0.0151(8) Uani 1 1 d . . . . .
C3 C 0.8444(4) 0.00161(18) 0.4360(5) 0.0159(8) Uani 1 1 d . . . . .
H3 H 0.829258 -0.039170 0.449652 0.019 Uiso 1 1 calc R U . . .
C4 C 0.9533(4) 0.02056(17) 0.3732(4) 0.0148(8) Uani 1 1 d . . . . .
C5 C 0.9709(4) 0.08057(17) 0.3496(5) 0.0161(8) Uani 1 1 d . . . . .
C6 C 0.8815(4) 0.11942(17) 0.3967(5) 0.0186(8) Uani 1 1 d . . . . .
H6 H 0.893584 0.160418 0.382433 0.022 Uiso 1 1 calc R U . . .
N7 N 0.5704(3) 0.07662(16) 0.5794(4) 0.0177(7) Uani 1 1 d . . . . .
C8 C 0.6382(5) 0.02924(16) 0.5441(6) 0.0147(7) Uani 1 1 d . . . . .
C9 C 0.5961(4) -0.02765(18) 0.5637(5) 0.0202(9) Uani 1 1 d . . . . .
H9 H 0.645873 -0.060489 0.539131 0.024 Uiso 1 1 calc R U . . .
C10 C 0.4792(4) -0.03541(19) 0.6202(5) 0.0224(9) Uani 1 1 d . . . . .
H10 H 0.447290 -0.074001 0.633235 0.027 Uiso 1 1 calc R U . . .
C11 C 0.4098(4) 0.0122(2) 0.6572(5) 0.0209(10) Uani 1 1 d . . . . .
H11 H 0.329887 0.007369 0.696791 0.025 Uiso 1 1 calc R U . . .
C12 C 0.4589(4) 0.06812(19) 0.6354(5) 0.0223(9) Uani 1 1 d . . . . .
H12 H 0.411203 0.101461 0.661468 0.027 Uiso 1 1 calc R U . . .
C13 C 1.0589(4) -0.02185(17) 0.3443(5) 0.0161(8) Uani 1 1 d . . . . .
O14 O 1.1735(3) -0.00949(13) 0.3764(4) 0.0233(6) Uani 1 1 d . . . . .
O15 O 1.0079(3) -0.07307(12) 0.2822(3) 0.0198(6) Uani 1 1 d . . . . .
C16 C 1.1056(5) -0.11777(18) 0.2682(5) 0.0244(9) Uani 1 1 d . . . . .
H16A H 1.157041 -0.105258 0.184861 0.037 Uiso 1 1 calc R U . . .
H16B H 1.060620 -0.154953 0.231494 0.037 Uiso 1 1 calc R U . . .
H16C H 1.164922 -0.123258 0.378767 0.037 Uiso 1 1 calc R U . . .
C17 C 1.0782(4) 0.10404(17) 0.2689(5) 0.0173(8) Uani 1 1 d . . . . .
O18 O 1.1059(3) 0.08383(13) 0.1436(4) 0.0274(7) Uani 1 1 d . . . . .
O19 O 1.1357(3) 0.14995(11) 0.3541(4) 0.0235(7) Uani 1 1 d . . . . .
C20 C 1.2393(5) 0.1773(2) 0.2856(6) 0.0310(11) Uani 1 1 d . . . . .
H20A H 1.311585 0.149106 0.287967 0.046 Uiso 1 1 calc R U . . .
H20B H 1.272716 0.211821 0.353845 0.046 Uiso 1 1 calc R U . . .
H20C H 1.204126 0.189421 0.168229 0.046 Uiso 1 1 calc R U . . .
O21 O 0.8232(3) 0.19140(13) 0.7401(4) 0.0276(7) Uani 1 1 d . . . . .
N22 N 0.8239(4) 0.17178(15) 0.8867(5) 0.0237(8) Uani 1 1 d . . . . .
O23 O 0.7386(4) 0.13483(16) 0.9055(5) 0.0384(9) Uani 1 1 d . . . . .
O24 O 0.9079(3) 0.18925(14) 1.0109(4) 0.0309(8) Uani 1 1 d . . . . .
O25 O 0.6998(3) 0.22368(13) 0.4024(4) 0.0223(6) Uani 1 1 d . . . . .
N26 N 0.6331(4) 0.21762(15) 0.2475(5) 0.0229(8) Uani 1 1 d . . . . .
O27 O 0.5522(3) 0.17658(15) 0.2192(4) 0.0295(7) Uani 1 1 d . . . . .
O28 O 0.6524(4) 0.25211(14) 0.1396(4) 0.0324(8) Uani 1 1 d . . . . .
O29 O 0.5165(4) 0.20265(14) 0.6073(4) 0.0282(7) Uani 1 1 d D . . . .
H29A H 0.501(5) 0.202(2) 0.706(4) 0.033(14) Uiso 1 1 d D . . . .
H29B H 0.494(6) 0.2342(17) 0.554(7) 0.06(2) Uiso 1 1 d D . . . .
O50W O 0.9092(4) 0.31106(16) 0.3723(4) 0.0306(8) Uani 1 1 d D . . . .
H50A H 0.958(5) 0.307(3) 0.468(4) 0.049(18) Uiso 1 1 d D . . . .
H50B H 0.848(6) 0.287(3) 0.379(10) 0.10(3) 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
Cu1 O29 1.935(3) . ?
Cu1 N1 1.988(3) . ?
Cu1 N7 2.018(4) . ?
Cu1 O25 2.047(3) . ?
Cu1 O21 2.270(3) . ?
N1 C6 1.331(5) . ?
N1 C2 1.351(5) . ?
C2 C3 1.390(6) . ?
C2 C8 1.479(6) . ?
C3 C4 1.393(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(5) . ?
C4 C13 1.508(6) . ?
C5 C6 1.385(6) . ?
C5 C17 1.493(6) . ?
C6 H6 0.9500 . ?
N7 C12 1.334(5) . ?
N7 C8 1.347(5) . ?
C8 C9 1.383(5) . ?
C9 C10 1.386(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.365(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 O14 1.192(5) . ?
C13 O15 1.332(5) . ?
O15 C16 1.452(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 O18 1.196(4) . ?
C17 O19 1.321(5) . ?
O19 C20 1.441(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O21 N22 1.261(5) . ?
N22 O24 1.247(5) . ?
N22 O23 1.249(5) . ?
O25 N26 1.302(5) . ?
N26 O28 1.217(4) . ?
N26 O27 1.241(5) . ?
O29 H29A 0.85(2) . ?
O29 H29B 0.84(2) . ?
O50W H50A 0.83(2) . ?
O50W H50B 0.85(2) . ?

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
O29 Cu1 N1 174.40(16) . . ?
O29 Cu1 N7 95.84(13) . . ?
N1 Cu1 N7 80.73(15) . . ?
O29 Cu1 O25 89.16(13) . . ?
N1 Cu1 O25 92.17(13) . . ?
N7 Cu1 O25 155.32(13) . . ?
O29 Cu1 O21 96.19(14) . . ?
N1 Cu1 O21 89.38(13) . . ?
N7 Cu1 O21 120.68(12) . . ?
O25 Cu1 O21 82.54(12) . . ?
C6 N1 C2 119.9(3) . . ?
C6 N1 Cu1 124.7(3) . . ?
C2 N1 Cu1 115.5(3) . . ?
N1 C2 C3 121.1(4) . . ?
N1 C2 C8 114.5(3) . . ?
C3 C2 C8 124.4(3) . . ?
C2 C3 C4 118.9(4) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 119.3(4) . . ?
C3 C4 C13 121.4(3) . . ?
C5 C4 C13 119.0(4) . . ?
C6 C5 C4 118.2(4) . . ?
C6 C5 C17 119.1(3) . . ?
C4 C5 C17 122.6(3) . . ?
N1 C6 C5 122.5(4) . . ?
N1 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C12 N7 C8 118.6(4) . . ?
C12 N7 Cu1 126.7(3) . . ?
C8 N7 Cu1 114.7(3) . . ?
N7 C8 C9 122.2(4) . . ?
N7 C8 C2 114.4(3) . . ?
C9 C8 C2 123.4(4) . . ?
C8 C9 C10 118.2(4) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
C11 C10 C9 120.2(4) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 118.4(4) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
N7 C12 C11 122.5(4) . . ?
N7 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
O14 C13 O15 125.9(4) . . ?
O14 C13 C4 122.2(4) . . ?
O15 C13 C4 111.9(3) . . ?
C13 O15 C16 114.4(3) . . ?
O15 C16 H16A 109.5 . . ?
O15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O18 C17 O19 125.6(4) . . ?
O18 C17 C5 123.9(4) . . ?
O19 C17 C5 110.5(3) . . ?
C17 O19 C20 115.5(3) . . ?
O19 C20 H20A 109.5 . . ?
O19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N22 O21 Cu1 112.4(3) . . ?
O24 N22 O23 120.6(4) . . ?
O24 N22 O21 120.6(4) . . ?
O23 N22 O21 118.8(4) . . ?
N26 O25 Cu1 108.1(2) . . ?
O28 N26 O27 123.7(4) . . ?
O28 N26 O25 119.0(4) . . ?
O27 N26 O25 117.3(3) . . ?
Cu1 O29 H29A 122(4) . . ?
Cu1 O29 H29B 119(4) . . ?
H29A O29 H29B 114(5) . . ?
H50A O50W H50B 101(6) . . ?

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
C6 N1 C2 C3 2.5(6) . . . . ?
Cu1 N1 C2 C3 -176.0(3) . . . . ?
C6 N1 C2 C8 -177.3(4) . . . . ?
Cu1 N1 C2 C8 4.3(5) . . . . ?
N1 C2 C3 C4 -0.6(6) . . . . ?
C8 C2 C3 C4 179.1(4) . . . . ?
C2 C3 C4 C5 -2.0(6) . . . . ?
C2 C3 C4 C13 172.7(3) . . . . ?
C3 C4 C5 C6 2.7(6) . . . . ?
C13 C4 C5 C6 -172.1(3) . . . . ?
C3 C4 C5 C17 -174.5(4) . . . . ?
C13 C4 C5 C17 10.7(6) . . . . ?
C2 N1 C6 C5 -1.7(6) . . . . ?
Cu1 N1 C6 C5 176.5(3) . . . . ?
C4 C5 C6 N1 -0.9(6) . . . . ?
C17 C5 C6 N1 176.4(4) . . . . ?
C12 N7 C8 C9 0.1(6) . . . . ?
Cu1 N7 C8 C9 179.4(3) . . . . ?
C12 N7 C8 C2 178.4(4) . . . . ?
Cu1 N7 C8 C2 -2.3(5) . . . . ?
N1 C2 C8 N7 -1.3(6) . . . . ?
C3 C2 C8 N7 179.0(4) . . . . ?
N1 C2 C8 C9 177.0(4) . . . . ?
C3 C2 C8 C9 -2.7(7) . . . . ?
N7 C8 C9 C10 0.6(6) . . . . ?
C2 C8 C9 C10 -177.5(4) . . . . ?
C8 C9 C10 C11 -0.9(6) . . . . ?
C9 C10 C11 C12 0.5(6) . . . . ?
C8 N7 C12 C11 -0.6(6) . . . . ?
Cu1 N7 C12 C11 -179.8(3) . . . . ?
C10 C11 C12 N7 0.3(7) . . . . ?
C3 C4 C13 O14 -140.4(4) . . . . ?
C5 C4 C13 O14 34.3(5) . . . . ?
C3 C4 C13 O15 39.0(5) . . . . ?
C5 C4 C13 O15 -146.3(4) . . . . ?
O14 C13 O15 C16 5.4(5) . . . . ?
C4 C13 O15 C16 -174.0(3) . . . . ?
C6 C5 C17 O18 -132.8(4) . . . . ?
C4 C5 C17 O18 44.4(6) . . . . ?
C6 C5 C17 O19 46.6(5) . . . . ?
C4 C5 C17 O19 -136.3(4) . . . . ?
O18 C17 O19 C20 0.7(6) . . . . ?
C5 C17 O19 C20 -178.7(4) . . . . ?
Cu1 O21 N22 O24 -177.2(3) . . . . ?
Cu1 O21 N22 O23 2.4(5) . . . . ?
Cu1 O25 N26 O28 -175.4(3) . . . . ?
Cu1 O25 N26 O27 4.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#C12  H12  O29   0.95    2.62    3.131(5) 114.3  .     yes
#C12  H12  O50W  0.95    2.62    3.441(5) 145.3  4_455 yes
#C20  H20B N22   0.98    2.70    3.592(6) 151.6  4_554 yes
C3 H3 O23 0.95 2.36 3.280(5) 161.6 2_554 yes
C6 H6 O25 0.95 2.50 3.029(5) 115.5 . yes
C9 H9 O23 0.95 2.31 3.239(6) 164.6 2_554 yes
C11 H11 O14 0.95 2.38 3.293(5) 161.1 2_455 yes
C16 H16B O21 0.98 2.60 3.329(6) 131.0 2_554 yes
C16 H16B O28 0.98 2.49 3.203(5) 129.5 3_545 yes
C16 H16C O18 0.98 2.50 3.120(5) 120.9 2 yes
C20 H20B O21 0.98 2.48 3.150(6) 125.4 4_554 yes
O29 H29A O50W 0.85(2) 1.81(3) 2.618(5) 158(5) 4_455 yes
O29 H29B O24 0.84(2) 1.95(3) 2.745(4) 157(6) 4_454 yes
O50W H50A O27 0.83(2) 2.09(3) 2.894(5) 162(6) 4 yes
O50W H50B O25 0.85(2) 2.13(2) 2.982(5) 178(8) . yes
#O50W H50B O28   0.85(2) 2.61(6) 3.209(5) 129(7) .     yes

_refine_diff_density_max         0.501
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2041821'
loop_
_audit_author_name
_audit_author_address
'Marta Pockaj'
;University of Ljubljana, Faculty of Chemistry and Chemical Technology
Slovenia
;
_audit_update_record             
;
2020-11-01 deposited with the CCDC.	2021-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 Cl4 Cu2 N4 O8 S2'
_chemical_formula_sum            'C24 H20 Cl4 Cu2 N4 O8 S2'
_chemical_formula_weight         825.44

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'
Cu Cu -1.9646 0.5888 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7848(5)
_cell_length_b                   9.0261(6)
_cell_length_c                   11.9040(5)
_cell_angle_alpha                101.778(4)
_cell_angle_beta                 100.435(4)
_cell_angle_gamma                109.621(6)
_cell_volume                     742.48(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3098
_cell_measurement_theta_min      3.8910
_cell_measurement_theta_max      74.6270

_exptl_crystal_description       platelet
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_F_000             414
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    6.887
_shelx_estimated_absorpt_T_min   0.425
_shelx_estimated_absorpt_T_max   0.875
_exptl_absorpt_correction_T_min  0.25983
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.4933
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            7240
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.941
_diffrn_reflns_theta_max         75.246
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3047
_reflns_number_gt                2666
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0723P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3047
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1108
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.78856(5) 0.49553(4) 0.52200(3) 0.01654(14) Uani 1 1 d . . . . .
Cl1 Cl 0.84634(8) 0.30699(7) 0.39366(5) 0.01860(16) Uani 1 1 d . . . . .
Cl2 Cl 0.74391(10) 0.34636(8) 0.65009(5) 0.02501(17) Uani 1 1 d . . . . .
N1 N 0.7655(3) 0.6273(3) 0.40142(18) 0.0178(4) Uani 1 1 d . . . . .
C2 C 0.7416(4) 0.7678(3) 0.4448(2) 0.0186(5) Uani 1 1 d . . . . .
C3 C 0.7341(4) 0.8765(3) 0.3787(2) 0.0202(5) Uani 1 1 d . . . . .
H3 H 0.724147 0.976984 0.412970 0.024 Uiso 1 1 calc R U . . .
C4 C 0.7415(4) 0.8349(3) 0.2607(2) 0.0194(5) Uani 1 1 d . . . . .
C5 C 0.7585(4) 0.6871(3) 0.2140(2) 0.0194(5) Uani 1 1 d . . . . .
C6 C 0.7751(4) 0.5890(3) 0.2890(2) 0.0196(5) Uani 1 1 d . . . . .
H6 H 0.793875 0.491491 0.258786 0.023 Uiso 1 1 calc R U . . .
C7 C 0.7157(4) 0.7846(3) 0.5640(2) 0.0189(5) Uani 1 1 d . . . . .
S8 S 0.66708(10) 0.93549(8) 0.64858(6) 0.02445(17) Uani 1 1 d . . . . .
C9 C 0.6484(4) 0.8341(4) 0.7550(2) 0.0250(5) Uani 1 1 d . . . . .
H9 H 0.620573 0.871155 0.827500 0.030 Uiso 1 1 calc R U . . .
C10 C 0.6784(4) 0.6939(3) 0.7225(2) 0.0220(5) Uani 1 1 d . . . . .
H10 H 0.673438 0.621160 0.770472 0.026 Uiso 1 1 calc R U . . .
N11 N 0.7164(3) 0.6672(3) 0.61397(19) 0.0191(4) Uani 1 1 d . . . . .
C12 C 0.7149(4) 0.9448(3) 0.1852(2) 0.0205(5) Uani 1 1 d . . . . .
O13 O 0.5648(3) 0.9550(2) 0.15285(17) 0.0252(4) Uani 1 1 d . . . . .
O14 O 0.8758(3) 1.0282(3) 0.16433(17) 0.0250(4) Uani 1 1 d . . . . .
C15 C 0.8637(5) 1.1359(4) 0.0912(3) 0.0310(6) Uani 1 1 d . . . . .
H15A H 0.744604 1.082813 0.027710 0.047 Uiso 1 1 calc R U . . .
H15B H 0.970616 1.159093 0.055731 0.047 Uiso 1 1 calc R U . . .
H15C H 0.867782 1.238890 0.140501 0.047 Uiso 1 1 calc R U . . .
C16 C 0.7461(4) 0.6280(3) 0.0851(2) 0.0208(5) Uani 1 1 d . . . . .
O17 O 0.6995(4) 0.6910(3) 0.01135(17) 0.0320(5) Uani 1 1 d . . . . .
O18 O 0.7837(3) 0.4937(2) 0.06050(16) 0.0239(4) Uani 1 1 d . . . . .
C19 C 0.7652(4) 0.4248(3) -0.0644(2) 0.0253(5) Uani 1 1 d . . . . .
H19A H 0.637620 0.402373 -0.111672 0.038 Uiso 1 1 calc R U . . .
H19B H 0.786529 0.322455 -0.075056 0.038 Uiso 1 1 calc R U . . .
H19C H 0.859065 0.503211 -0.090851 0.038 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 N11 2.007(2) . ?
Cu1 N1 2.062(2) . ?
Cu1 Cl2 2.2304(7) . ?
Cu1 Cl1 2.2658(6) . ?
Cu1 Cl1 2.6640(7) 2_766 ?
N1 C6 1.334(3) . ?
N1 C2 1.355(3) . ?
C2 C3 1.386(3) . ?
C2 C7 1.454(3) . ?
C3 C4 1.395(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(4) . ?
C4 C12 1.507(3) . ?
C5 C6 1.399(3) . ?
C5 C16 1.492(3) . ?
C6 H6 0.9500 . ?
C7 N11 1.318(3) . ?
C7 S8 1.713(3) . ?
S8 C9 1.707(3) . ?
C9 C10 1.355(4) . ?
C9 H9 0.9500 . ?
C10 N11 1.369(3) . ?
C10 H10 0.9500 . ?
C12 O13 1.202(4) . ?
C12 O14 1.324(4) . ?
O14 C15 1.446(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 O17 1.205(3) . ?
C16 O18 1.329(3) . ?
O18 C19 1.450(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N11 Cu1 N1 79.32(9) . . ?
N11 Cu1 Cl2 93.22(7) . . ?
N1 Cu1 Cl2 166.63(7) . . ?
N11 Cu1 Cl1 171.49(7) . . ?
N1 Cu1 Cl1 93.12(6) . . ?
Cl2 Cu1 Cl1 93.41(3) . . ?
N11 Cu1 Cl1 90.59(7) . 2_766 ?
N1 Cu1 Cl1 88.00(6) . 2_766 ?
Cl2 Cu1 Cl1 103.28(3) . 2_766 ?
Cl1 Cu1 Cl1 93.08(2) . 2_766 ?
Cu1 Cl1 Cu1 86.92(2) . 2_766 ?
C6 N1 C2 118.6(2) . . ?
C6 N1 Cu1 126.74(18) . . ?
C2 N1 Cu1 114.67(17) . . ?
N1 C2 C3 122.7(2) . . ?
N1 C2 C7 112.1(2) . . ?
C3 C2 C7 125.2(2) . . ?
C2 C3 C4 118.5(2) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 C12 118.6(2) . . ?
C5 C4 C12 122.1(2) . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 C16 121.3(2) . . ?
C6 C5 C16 120.0(2) . . ?
N1 C6 C5 122.5(2) . . ?
N1 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
N11 C7 C2 118.7(2) . . ?
N11 C7 S8 113.3(2) . . ?
C2 C7 S8 127.9(2) . . ?
C9 S8 C7 89.67(13) . . ?
C10 C9 S8 111.2(2) . . ?
C10 C9 H9 124.4 . . ?
S8 C9 H9 124.4 . . ?
C9 C10 N11 113.5(2) . . ?
C9 C10 H10 123.2 . . ?
N11 C10 H10 123.2 . . ?
C7 N11 C10 112.3(2) . . ?
C7 N11 Cu1 114.31(18) . . ?
C10 N11 Cu1 133.23(19) . . ?
O13 C12 O14 126.4(2) . . ?
O13 C12 C4 122.2(3) . . ?
O14 C12 C4 111.4(2) . . ?
C12 O14 C15 115.4(2) . . ?
O14 C15 H15A 109.5 . . ?
O14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O17 C16 O18 124.1(2) . . ?
O17 C16 C5 123.7(3) . . ?
O18 C16 C5 112.1(2) . . ?
C16 O18 C19 115.0(2) . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
C6 N1 C2 C3 -2.6(4) . . . . ?
Cu1 N1 C2 C3 176.3(2) . . . . ?
C6 N1 C2 C7 174.5(2) . . . . ?
Cu1 N1 C2 C7 -6.6(3) . . . . ?
N1 C2 C3 C4 3.5(4) . . . . ?
C7 C2 C3 C4 -173.2(2) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C2 C3 C4 C12 174.3(2) . . . . ?
C3 C4 C5 C6 -2.5(4) . . . . ?
C12 C4 C5 C6 -177.4(2) . . . . ?
C3 C4 C5 C16 173.3(2) . . . . ?
C12 C4 C5 C16 -1.6(4) . . . . ?
C2 N1 C6 C5 -1.0(4) . . . . ?
Cu1 N1 C6 C5 -179.74(19) . . . . ?
C4 C5 C6 N1 3.5(4) . . . . ?
C16 C5 C6 N1 -172.4(2) . . . . ?
N1 C2 C7 N11 -0.6(4) . . . . ?
C3 C2 C7 N11 176.4(3) . . . . ?
N1 C2 C7 S8 -175.76(19) . . . . ?
C3 C2 C7 S8 1.2(4) . . . . ?
N11 C7 S8 C9 0.2(2) . . . . ?
C2 C7 S8 C9 175.6(3) . . . . ?
C7 S8 C9 C10 -0.2(2) . . . . ?
S8 C9 C10 N11 0.1(3) . . . . ?
C2 C7 N11 C10 -176.0(2) . . . . ?
S8 C7 N11 C10 -0.2(3) . . . . ?
C2 C7 N11 Cu1 7.7(3) . . . . ?
S8 C7 N11 Cu1 -176.45(11) . . . . ?
C9 C10 N11 C7 0.0(4) . . . . ?
C9 C10 N11 Cu1 175.4(2) . . . . ?
C3 C4 C12 O13 -69.6(3) . . . . ?
C5 C4 C12 O13 105.3(3) . . . . ?
C3 C4 C12 O14 108.4(3) . . . . ?
C5 C4 C12 O14 -76.7(3) . . . . ?
O13 C12 O14 C15 -2.7(4) . . . . ?
C4 C12 O14 C15 179.3(2) . . . . ?
C4 C5 C16 O17 -9.0(4) . . . . ?
C6 C5 C16 O17 166.8(3) . . . . ?
C4 C5 C16 O18 173.9(2) . . . . ?
C6 C5 C16 O18 -10.2(4) . . . . ?
O17 C16 O18 C19 0.1(4) . . . . ?
C5 C16 O18 C19 177.1(2) . . . . ?

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
#C3 H3 Cl1  0.95 2.88 3.643(3) 138.3 1_565 yes
C6 H6 Cl1 0.95 2.61 3.215(3) 121.6 . yes
C9 H9 O13 0.95 2.47 3.084(3) 122.4 2_676 yes

_refine_diff_density_max         0.772
_refine_diff_density_min         -0.835
_refine_diff_density_rms         0.123

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2041823'
loop_
_audit_author_name
_audit_author_address
'Marta Pockaj'
;University of Ljubljana, Faculty of Chemistry and Chemical Technology
Slovenia
;
_audit_update_record             
;
2020-11-01 deposited with the CCDC.	2021-01-18 downloaded from the CCDC.
;

_vrf_PLAT002_shelx               
;
RESPONSE:
Hydrogens H29A and H29B, residing on O29, were obtained
from difference Fourier map. The distances towards O29 
were restraind to be 0.85(2) A to obtain realistic bondlengths.
;

_vrf_PLAT172_shelx               
;
RESPONSE:
Hydrogens H29A and H29B, residing on O29, were obtained
from difference Fourier map. The distances towards O29 
were restraind to be 0.85(2) A to obtain realistic bondlengths.
;

_vrf_PLAT860_shelx               
;
RESPONSE:
Hydrogens H29A and H29B, residing on O29, were obtained
from difference Fourier map. The distances towards O29 
were restraind to be 0.85(2) A to obtain realistic bondlengths.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H14 Cu N4 O11 S'
_chemical_formula_sum            'C13 H14 Cu N4 O11 S'
_chemical_formula_weight         497.88

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'
S S 0.1246 0.1234 '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 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1313(6)
_cell_length_b                   24.6456(11)
_cell_length_c                   8.5875(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.946(7)
_cell_angle_gamma                90
_cell_volume                     1848.67(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3367
_cell_measurement_theta_min      2.9510
_cell_measurement_theta_max      29.2100

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.789
_exptl_crystal_F_000             1012
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.364
_shelx_estimated_absorpt_T_min   0.647
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_T_min  0.75049
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.4933
_diffrn_reflns_number            10122
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.614
_diffrn_reflns_theta_max         30.380
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4849
_reflns_number_gt                3819
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0293P)²+0.9610P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4849
_refine_ls_number_parameters     282
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0846
_refine_ls_wR_factor_gt          0.0769
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.043
_refine_ls_shift/su_mean         0.001

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 0.80325(3) 0.58736(2) 0.53812(3) 0.01597(8) Uani 1 1 d . . . . .
N1 N 0.7149(2) 0.66478(7) 0.5172(2) 0.0148(4) Uani 1 1 d . . . . .
C2 C 0.8076(3) 0.69988(9) 0.6221(3) 0.0152(4) Uani 1 1 d . . . . .
C3 C 0.7837(3) 0.75549(9) 0.6134(3) 0.0171(5) Uani 1 1 d . . . . .
H3 H 0.852045 0.779232 0.687096 0.021 Uiso 1 1 calc R U . . .
C4 C 0.6574(3) 0.77579(9) 0.4944(3) 0.0157(5) Uani 1 1 d . . . . .
C5 C 0.5607(3) 0.73969(9) 0.3882(3) 0.0153(5) Uani 1 1 d . . . . .
C6 C 0.5942(3) 0.68451(9) 0.4044(3) 0.0160(5) Uani 1 1 d . . . . .
H6 H 0.528005 0.659911 0.331673 0.019 Uiso 1 1 calc R U . . .
C7 C 0.9358(3) 0.67379(9) 0.7396(3) 0.0154(5) Uani 1 1 d . . . . .
S8 S 1.06290(7) 0.70454(2) 0.89975(7) 0.01953(13) Uani 1 1 d . . . . .
C9 C 1.1562(3) 0.64410(9) 0.9502(3) 0.0206(5) Uani 1 1 d . . . . .
H9 H 1.244412 0.639184 1.040717 0.025 Uiso 1 1 calc R U . . .
C10 C 1.0890(3) 0.60388(9) 0.8453(3) 0.0198(5) Uani 1 1 d . . . . .
N11 N 0.9601(2) 0.62136(7) 0.7255(2) 0.0161(4) Uani 1 1 d . . . . .
C12 C 0.6223(3) 0.83566(9) 0.4950(3) 0.0164(5) Uani 1 1 d . . . . .
O13 O 0.5167(2) 0.85237(7) 0.5372(2) 0.0248(4) Uani 1 1 d . . . . .
O14 O 0.7250(2) 0.86493(6) 0.4515(2) 0.0236(4) Uani 1 1 d . . . . .
C15 C 0.7009(4) 0.92342(10) 0.4536(4) 0.0348(7) Uani 1 1 d . . . . .
H15A H 0.603869 0.932815 0.372985 0.052 Uiso 1 1 calc R U . . .
H15B H 0.785136 0.942227 0.427028 0.052 Uiso 1 1 calc R U . . .
H15C H 0.697589 0.934496 0.562088 0.052 Uiso 1 1 calc R U . . .
C16 C 0.4223(3) 0.75721(9) 0.2555(3) 0.0169(5) Uani 1 1 d . . . . .
O17 O 0.3110(2) 0.72932(7) 0.2050(2) 0.0259(4) Uani 1 1 d . . . . .
O18 O 0.44024(19) 0.80693(6) 0.20305(19) 0.0211(4) Uani 1 1 d . . . . .
C19 C 0.3070(3) 0.83000(10) 0.0845(3) 0.0243(6) Uani 1 1 d . . . . .
H19A H 0.284447 0.809152 -0.016902 0.036 Uiso 1 1 calc R U . . .
H19B H 0.328079 0.867816 0.063052 0.036 Uiso 1 1 calc R U . . .
H19C H 0.218822 0.828557 0.127596 0.036 Uiso 1 1 calc R U . . .
C20 C 1.1457(3) 0.54723(10) 0.8527(3) 0.0319(7) Uani 1 1 d . . . . .
H20A H 1.073391 0.522906 0.882605 0.048 Uiso 1 1 calc R U . . .
H20B H 1.246012 0.544657 0.934412 0.048 Uiso 1 1 calc R U . . .
H20C H 1.155215 0.536731 0.746016 0.048 Uiso 1 1 calc R U . . .
O21 O 0.9812(2) 0.56447(6) 0.4182(2) 0.0234(4) Uani 1 1 d . . . . .
N22 N 1.0095(3) 0.60631(8) 0.3422(2) 0.0226(5) Uani 1 1 d . . . . .
O23 O 0.9418(3) 0.64917(7) 0.3523(2) 0.0362(5) Uani 1 1 d . . . . .
O24 O 1.1024(3) 0.60270(8) 0.2657(3) 0.0447(6) Uani 1 1 d . . . . .
O25 O 0.6503(2) 0.56193(6) 0.34248(19) 0.0206(4) Uani 1 1 d . . . . .
N26 N 0.5193(2) 0.55158(8) 0.3675(3) 0.0214(4) Uani 1 1 d . . . . .
O27 O 0.5038(2) 0.56119(7) 0.5027(2) 0.0260(4) Uani 1 1 d . . . . .
O28 O 0.4168(2) 0.53266(7) 0.2543(2) 0.0307(4) Uani 1 1 d . . . . .
O29 O 0.8233(2) 0.51387(7) 0.6413(2) 0.0228(4) Uani 1 1 d D . . . .
H29A H 0.748(3) 0.5003(12) 0.662(4) 0.040(9) Uiso 1 1 d D . . . .
H29B H 0.882(4) 0.4893(11) 0.623(4) 0.063(12) 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
Cu1 O25 1.9488(16) . ?
Cu1 N11 1.9999(19) . ?
Cu1 O29 2.0010(17) . ?
Cu1 N1 2.0590(18) . ?
Cu1 O21 2.2349(17) . ?
N1 C6 1.330(3) . ?
N1 C2 1.353(3) . ?
C2 C3 1.386(3) . ?
C2 C7 1.454(3) . ?
C3 C4 1.392(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(3) . ?
C4 C12 1.510(3) . ?
C5 C6 1.392(3) . ?
C5 C16 1.498(3) . ?
C6 H6 0.9500 . ?
C7 N11 1.323(3) . ?
C7 S8 1.697(2) . ?
S8 C9 1.708(2) . ?
C9 C10 1.360(3) . ?
C9 H9 0.9500 . ?
C10 N11 1.387(3) . ?
C10 C20 1.484(3) . ?
C12 O13 1.198(3) . ?
C12 O14 1.321(3) . ?
O14 C15 1.459(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 O17 1.199(3) . ?
C16 O18 1.332(3) . ?
O18 C19 1.455(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O21 N22 1.286(3) . ?
N22 O24 1.218(3) . ?
N22 O23 1.240(3) . ?
O25 N26 1.301(3) . ?
N26 O28 1.228(3) . ?
N26 O27 1.233(3) . ?
O29 H29A 0.830(18) . ?
O29 H29B 0.854(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O25 Cu1 N11 173.51(7) . . ?
O25 Cu1 O29 92.34(7) . . ?
N11 Cu1 O29 94.10(8) . . ?
O25 Cu1 N1 93.37(7) . . ?
N11 Cu1 N1 81.51(7) . . ?
O29 Cu1 N1 149.35(8) . . ?
O25 Cu1 O21 87.49(7) . . ?
N11 Cu1 O21 91.71(7) . . ?
O29 Cu1 O21 89.46(7) . . ?
N1 Cu1 O21 120.85(7) . . ?
C6 N1 C2 118.42(19) . . ?
C6 N1 Cu1 128.53(15) . . ?
C2 N1 Cu1 112.42(15) . . ?
N1 C2 C3 122.6(2) . . ?
N1 C2 C7 113.58(19) . . ?
C3 C2 C7 123.8(2) . . ?
C2 C3 C4 118.6(2) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 C12 122.2(2) . . ?
C3 C4 C12 118.7(2) . . ?
C4 C5 C6 118.7(2) . . ?
C4 C5 C16 123.3(2) . . ?
C6 C5 C16 118.0(2) . . ?
N1 C6 C5 122.8(2) . . ?
N1 C6 H6 118.6 . . ?
C5 C6 H6 118.6 . . ?
N11 C7 C2 119.4(2) . . ?
N11 C7 S8 114.65(17) . . ?
C2 C7 S8 125.95(17) . . ?
C7 S8 C9 89.37(11) . . ?
C10 C9 S8 111.86(18) . . ?
C10 C9 H9 124.1 . . ?
S8 C9 H9 124.1 . . ?
C9 C10 N11 112.7(2) . . ?
C9 C10 C20 125.0(2) . . ?
N11 C10 C20 122.3(2) . . ?
C7 N11 C10 111.36(19) . . ?
C7 N11 Cu1 112.53(15) . . ?
C10 N11 Cu1 136.11(15) . . ?
O13 C12 O14 126.8(2) . . ?
O13 C12 C4 121.9(2) . . ?
O14 C12 C4 111.3(2) . . ?
C12 O14 C15 114.5(2) . . ?
O14 C15 H15A 109.5 . . ?
O14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O17 C16 O18 125.5(2) . . ?
O17 C16 C5 123.2(2) . . ?
O18 C16 C5 111.29(19) . . ?
C16 O18 C19 115.85(19) . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N22 O21 Cu1 108.18(14) . . ?
O24 N22 O23 122.7(2) . . ?
O24 N22 O21 119.3(2) . . ?
O23 N22 O21 118.0(2) . . ?
N26 O25 Cu1 112.52(14) . . ?
O28 N26 O27 123.3(2) . . ?
O28 N26 O25 117.9(2) . . ?
O27 N26 O25 118.8(2) . . ?
Cu1 O29 H29A 119(2) . . ?
Cu1 O29 H29B 123(2) . . ?
H29A O29 H29B 111(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
C6 N1 C2 C3 -1.8(3) . . . . ?
Cu1 N1 C2 C3 169.92(18) . . . . ?
C6 N1 C2 C7 -179.9(2) . . . . ?
Cu1 N1 C2 C7 -8.2(2) . . . . ?
N1 C2 C3 C4 1.5(3) . . . . ?
C7 C2 C3 C4 179.4(2) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C2 C3 C4 C12 174.1(2) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C12 C4 C5 C6 -174.6(2) . . . . ?
C3 C4 C5 C16 -179.7(2) . . . . ?
C12 C4 C5 C16 6.1(3) . . . . ?
C2 N1 C6 C5 1.0(3) . . . . ?
Cu1 N1 C6 C5 -169.17(17) . . . . ?
C4 C5 C6 N1 0.0(3) . . . . ?
C16 C5 C6 N1 179.4(2) . . . . ?
N1 C2 C7 N11 6.7(3) . . . . ?
C3 C2 C7 N11 -171.4(2) . . . . ?
N1 C2 C7 S8 -173.27(17) . . . . ?
C3 C2 C7 S8 8.7(3) . . . . ?
N11 C7 S8 C9 0.72(19) . . . . ?
C2 C7 S8 C9 -179.3(2) . . . . ?
C7 S8 C9 C10 0.3(2) . . . . ?
S8 C9 C10 N11 -1.2(3) . . . . ?
S8 C9 C10 C20 177.8(2) . . . . ?
C2 C7 N11 C10 178.5(2) . . . . ?
S8 C7 N11 C10 -1.5(3) . . . . ?
C2 C7 N11 Cu1 -1.5(3) . . . . ?
S8 C7 N11 Cu1 178.49(11) . . . . ?
C9 C10 N11 C7 1.7(3) . . . . ?
C20 C10 N11 C7 -177.3(2) . . . . ?
C9 C10 N11 Cu1 -178.29(18) . . . . ?
C20 C10 N11 Cu1 2.7(4) . . . . ?
C5 C4 C12 O13 67.4(3) . . . . ?
C3 C4 C12 O13 -106.8(3) . . . . ?
C5 C4 C12 O14 -115.4(2) . . . . ?
C3 C4 C12 O14 70.3(3) . . . . ?
O13 C12 O14 C15 -1.4(3) . . . . ?
C4 C12 O14 C15 -178.4(2) . . . . ?
C4 C5 C16 O17 -151.2(2) . . . . ?
C6 C5 C16 O17 29.4(3) . . . . ?
C4 C5 C16 O18 28.7(3) . . . . ?
C6 C5 C16 O18 -150.7(2) . . . . ?
O17 C16 O18 C19 5.4(3) . . . . ?
C5 C16 O18 C19 -174.48(19) . . . . ?
Cu1 O21 N22 O24 -179.0(2) . . . . ?
Cu1 O21 N22 O23 2.1(3) . . . . ?
Cu1 O25 N26 O28 -176.39(16) . . . . ?
Cu1 O25 N26 O27 3.7(2) . . . . ?

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
#C6  H6   O25  0.95      2.65      3.136(3) 112.2 .      yes
#C6  H6   N26  0.95      2.69      3.343(3) 126.3 .      yes
#C9  H9   O17  0.95      2.61      3.065(3) 110.0 1_656  yes
#C19 H19A O17  0.98      2.65      3.582(3) 159.9 4_575  yes
#C20 H20A O29  0.98      2.61      3.086(3) 110.2 .      yes
C3 H3 O23 0.95 2.26 3.176(3) 161.0 4_576 yes
C6 H6 O13 0.95 2.52 3.157(3) 124.6 4_575 yes
C9 H9 O13 0.95 2.50 3.157(3) 126.0 4_676 yes
C15 H15C O25 0.98 2.57 3.521(3) 164.0 4_576 yes
C19 H19B O27 0.98 2.53 3.413(3) 150.2 4_575 yes
O29 H29A O28 0.830(18) 2.018(18) 2.842(3) 172(3) 3_666 yes
O29 H29B O21 0.854(18) 1.923(19) 2.776(3) 178(4) 3_766 yes
O29 H29B N22 0.854(18) 2.54(2) 3.316(3) 152(3) 3_766 yes
O29 H29B O24 0.854(18) 2.45(3) 3.006(3) 124(3) 3_766 yes

_refine_diff_density_max         0.484
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.083

####################################################################### 
# 
# 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_mob668
_database_code_depnum_ccdc_archive 'CCDC 2041820'
loop_
_audit_author_name
_audit_author_address
'Marta Pockaj'
;University of Ljubljana, Faculty of Chemistry and Chemical Technology
Slovenia
;
_audit_update_record             
;
2020-11-01 deposited with the CCDC.	2021-01-18 downloaded from the CCDC.
;
_audit_creation_date             2019-06-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H24 Cl4 Cu2 N4 O8 S2'
_chemical_formula_sum            'C26 H24 Cl4 Cu2 N4 O8 S2'
_chemical_formula_weight         853.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H24 N4 O8 Cu1 Cl1'
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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.0032(7)
_cell_length_b                   17.3134(8)
_cell_length_c                   7.6901(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.719(5)
_cell_angle_gamma                90
_cell_volume                     1575.19(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3387
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.1590
_cell_measurement_theta_min      2.8910
_shelx_estimated_absorpt_T_max   0.912
_shelx_estimated_absorpt_T_min   0.834
_exptl_absorpt_coefficient_mu    1.878
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8104
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         2.353
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -61.00   1.00   18.65    --  -14.36-178.00   0.00   41
  2  ω     -4.00  25.00   1.00   18.65    --  -14.36 -99.00-120.00   29
  3  ω    -20.00  56.00   1.00   18.65    --   14.52 -99.00  30.00   76
  4  ω    -16.00  46.00   1.00   18.65    --   14.52  77.00-120.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0382172000
_diffrn_orient_matrix_UB_12      -0.0173391000
_diffrn_orient_matrix_UB_13      0.0492893000
_diffrn_orient_matrix_UB_21      -0.0421118000
_diffrn_orient_matrix_UB_22      0.0271414000
_diffrn_orient_matrix_UB_23      -0.0351865000
_diffrn_orient_matrix_UB_31      -0.0189681000
_diffrn_orient_matrix_UB_32      -0.0253261000
_diffrn_orient_matrix_UB_33      -0.0713553000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3090
_reflns_number_total             3608
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3608
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0315P)²+1.1890P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0787
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C9(H9)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_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
Cu1 Cu 0.66771(2) 0.74049(2) 0.65637(4) 0.01510(9) Uani 1 1 d . . . . .
Cl1 Cl 0.78877(5) 0.77393(3) 0.47270(7) 0.01816(13) Uani 1 1 d . . . . .
Cl2 Cl 0.61533(5) 0.86499(3) 0.68027(8) 0.02188(14) Uani 1 1 d . . . . .
S8 S 0.62422(5) 0.48507(3) 0.67997(9) 0.02033(14) Uani 1 1 d . . . . .
O18 O 0.14503(14) 0.74217(9) 0.7703(2) 0.0199(4) Uani 1 1 d . . . . .
O17 O 0.26876(14) 0.82611(9) 0.9193(2) 0.0201(4) Uani 1 1 d . . . . .
O14 O 0.20636(15) 0.52616(9) 0.8121(2) 0.0241(4) Uani 1 1 d . . . . .
O13 O 0.19759(16) 0.61757(10) 1.0173(2) 0.0278(4) Uani 1 1 d . . . . .
N1 N 0.51846(16) 0.70043(11) 0.7219(3) 0.0152(4) Uani 1 1 d . . . . .
N11 N 0.69326(16) 0.62281(11) 0.6428(2) 0.0157(4) Uani 1 1 d . . . . .
C2 C 0.50974(19) 0.62274(12) 0.7283(3) 0.0154(4) Uani 1 1 d . . . . .
C6 C 0.4339(2) 0.74303(13) 0.7627(3) 0.0161(5) Uani 1 1 d . . . . .
H6 H 0.439698 0.796550 0.759096 0.019 Uiso 1 1 calc R . . . .
C7 C 0.60766(19) 0.58308(13) 0.6828(3) 0.0149(4) Uani 1 1 d . . . . .
C3 C 0.41729(19) 0.58617(13) 0.7771(3) 0.0167(5) Uani 1 1 d . . . . .
H3 H 0.413893 0.532544 0.780704 0.020 Uiso 1 1 calc R . . . .
C12 C 0.2355(2) 0.59246(13) 0.8942(3) 0.0178(5) Uani 1 1 d . . . . .
C10 C 0.7787(2) 0.57434(13) 0.6095(3) 0.0195(5) Uani 1 1 d . . . . .
C5 C 0.33765(19) 0.71061(13) 0.8104(3) 0.0148(4) Uani 1 1 d . . . . .
C4 C 0.33007(19) 0.63030(13) 0.8206(3) 0.0153(5) Uani 1 1 d . . . . .
C16 C 0.24745(19) 0.76589(13) 0.8422(3) 0.0156(5) Uani 1 1 d . . . . .
C9 C 0.7538(2) 0.49830(13) 0.6227(3) 0.0201(5) Uani 1 1 d . . . . .
H9 H 0.801756 0.458267 0.602774 0.024 Uiso 1 1 calc R . . . .
C19 C 0.0539(2) 0.79275(16) 0.7991(4) 0.0278(6) Uani 1 1 d . . . . .
H19A H 0.060805 0.841304 0.741536 0.042 Uiso 1 1 calc GR . . . .
H19B H 0.057749 0.801124 0.923356 0.042 Uiso 1 1 calc GR . . . .
H19C H -0.017230 0.769388 0.751460 0.042 Uiso 1 1 calc GR . . . .
C20 C 0.8875(2) 0.60322(15) 0.5664(4) 0.0342(7) Uani 1 1 d . . . . .
H20A H 0.873147 0.632899 0.459473 0.051 Uiso 1 1 calc GR . . . .
H20B H 0.935340 0.560207 0.550821 0.051 Uiso 1 1 calc GR . . . .
H20C H 0.924259 0.635174 0.660952 0.051 Uiso 1 1 calc GR . . . .
C15 C 0.1290(2) 0.47755(16) 0.8884(4) 0.0328(6) Uani 1 1 d . . . . .
H15A H 0.052807 0.494344 0.847964 0.049 Uiso 1 1 calc GR . . . .
H15B H 0.145713 0.481134 1.014722 0.049 Uiso 1 1 calc GR . . . .
H15C H 0.137199 0.424949 0.853153 0.049 Uiso 1 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
Cu1 Cl1 2.2659(6) . ?
Cu1 Cl1 2.6264(7) 4_576 ?
Cu1 Cl2 2.2615(6) . ?
Cu1 N1 2.0613(19) . ?
Cu1 N11 2.0656(19) . ?
S8 C7 1.709(2) . ?
S8 C9 1.702(2) . ?
O18 C16 1.325(3) . ?
O18 C19 1.447(3) . ?
O17 C16 1.205(3) . ?
O14 C12 1.328(3) . ?
O14 C15 1.449(3) . ?
O13 C12 1.199(3) . ?
N1 C2 1.351(3) . ?
N1 C6 1.334(3) . ?
N11 C7 1.315(3) . ?
N11 C10 1.382(3) . ?
C2 C7 1.454(3) . ?
C2 C3 1.384(3) . ?
C6 C5 1.388(3) . ?
C3 C4 1.382(3) . ?
C12 C4 1.502(3) . ?
C10 C9 1.358(3) . ?
C10 C20 1.488(3) . ?
C5 C4 1.397(3) . ?
C5 C16 1.496(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Cu1 Cl1 106.79(2) . 4_576 ?
Cl2 Cu1 Cl1 91.35(2) . . ?
Cl2 Cu1 Cl1 97.66(2) . 4_576 ?
N1 Cu1 Cl1 156.00(6) . . ?
N1 Cu1 Cl1 96.28(6) . 4_576 ?
N1 Cu1 Cl2 92.05(5) . . ?
N1 Cu1 N11 79.81(7) . . ?
N11 Cu1 Cl1 83.64(5) . 4_576 ?
N11 Cu1 Cl1 95.99(6) . . ?
N11 Cu1 Cl2 171.85(6) . . ?
Cu1 Cl1 Cu1 103.90(2) . 4_575 ?
C9 S8 C7 89.03(11) . . ?
C16 O18 C19 114.87(18) . . ?
C12 O14 C15 116.42(19) . . ?
C2 N1 Cu1 114.82(15) . . ?
C6 N1 Cu1 126.77(15) . . ?
C6 N1 C2 118.4(2) . . ?
C7 N11 Cu1 112.06(15) . . ?
C7 N11 C10 111.04(19) . . ?
C10 N11 Cu1 136.84(16) . . ?
N1 C2 C7 113.0(2) . . ?
N1 C2 C3 122.4(2) . . ?
C3 C2 C7 124.6(2) . . ?
N1 C6 C5 122.6(2) . . ?
N11 C7 S8 114.78(17) . . ?
N11 C7 C2 120.28(19) . . ?
C2 C7 S8 124.93(17) . . ?
C4 C3 C2 119.2(2) . . ?
O14 C12 C4 110.66(19) . . ?
O13 C12 O14 125.7(2) . . ?
O13 C12 C4 123.4(2) . . ?
N11 C10 C20 123.0(2) . . ?
C9 C10 N11 113.3(2) . . ?
C9 C10 C20 123.7(2) . . ?
C6 C5 C4 118.8(2) . . ?
C6 C5 C16 116.2(2) . . ?
C4 C5 C16 124.9(2) . . ?
C3 C4 C12 120.1(2) . . ?
C3 C4 C5 118.5(2) . . ?
C5 C4 C12 121.1(2) . . ?
O18 C16 C5 112.32(19) . . ?
O17 C16 O18 125.3(2) . . ?
O17 C16 C5 122.3(2) . . ?
C10 C9 S8 111.83(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.281
_oxdiff_exptl_absorpt_empirical_full_min 0.768
####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2041822'
loop_
_audit_author_name
_audit_author_address
'Marta Pockaj'
;University of Ljubljana, Faculty of Chemistry and Chemical Technology
Slovenia
;
_audit_update_record             
;
2020-11-01 deposited with the CCDC.	2021-01-18 downloaded from the CCDC.
;

_vrf_PLAT420_shelx               
;
RESPONSE:
In the presence od many hydrogen bonds donors and acceptors,
O44A is not in the vicinity of any acceptor, but its position is ok.
;

_vrf_PLAT230_shelx               
;
RESPONSE:
The outermost oxygen atom of coordinated nitrate anion vibrates
more pronouncedly compared to its neighbours.
;

_vrf_PLAT002_shelx               
; 
RESPONSE: The O-H distances were restrained to 0.85(2) A in
several cases.
;

_vrf_PLAT172_shelx               
; 
RESPONSE: The O-H distances were restrained to 0.85(2) A in
several cases.
;

_vrf_PLAT007_shelx               
; 
RESPONSE: 
The geometry of water (O44) could not be obtained by using dfix restraints
and was consequently treated with afix 7 contraint.
;

_vrf_PLAT860_shelx               
; 
RESPONSE: The O-H distances were restrained to 0.85(2) A in
several cases.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 Cu N3 O10 S, N O3'
_chemical_formula_sum            'C12 H16 Cu N4 O13 S'
_chemical_formula_weight         519.89

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8810(3)
_cell_length_b                   12.4005(4)
_cell_length_c                   20.9376(6)
_cell_angle_alpha                79.593(3)
_cell_angle_beta                 88.991(2)
_cell_angle_gamma                88.486(3)
_cell_volume                     2011.66(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    10260
_cell_measurement_theta_min      2.9950
_cell_measurement_theta_max      30.1920

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_F_000             1060
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.265
_shelx_estimated_absorpt_T_min   0.570
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_T_min  0.69363
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.4933
_diffrn_reflns_number            25294
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.348
_diffrn_reflns_theta_max         30.456
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10742
_reflns_number_gt                9105
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²+1.5397P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10742
_refine_ls_number_parameters     594
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1029
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000

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 0.45305(3) 0.71342(2) 0.10261(2) 0.01462(7) Uani 1 1 d . . . . .
Cu2 Cu -0.04393(3) 0.28929(2) 0.39658(2) 0.01427(7) Uani 1 1 d . . . . .
N1 N 0.3782(2) 0.86456(14) 0.11947(8) 0.0142(3) Uani 1 1 d . . . . .
N11 N 0.3811(2) 0.77962(14) 0.01389(8) 0.0149(3) Uani 1 1 d . . . . .
N23 N 0.8704(2) 0.75359(17) 0.06761(9) 0.0217(4) Uani 1 1 d . . . . .
N27 N 0.6863(3) 0.39202(15) 0.20464(9) 0.0217(4) Uani 1 1 d . . . . .
N31 N -0.1102(2) 0.13963(14) 0.37994(8) 0.0138(3) Uani 1 1 d . . . . .
N41 N -0.1189(2) 0.22463(14) 0.48534(8) 0.0152(3) Uani 1 1 d . . . . .
N53 N 0.3677(2) 0.24624(17) 0.43806(9) 0.0225(4) Uani 1 1 d . . . . .
N57 N 0.1788(3) 0.60859(15) 0.29448(9) 0.0218(4) Uani 1 1 d . . . . .
O13 O 0.2459(2) 1.00391(14) 0.29079(7) 0.0226(3) Uani 1 1 d . . . . .
O14 O 0.4551(2) 1.11463(14) 0.24607(8) 0.0231(3) Uani 1 1 d . . . . .
O17 O 0.1523(2) 1.21081(14) 0.18480(8) 0.0295(4) Uani 1 1 d . . . . .
O18 O 0.1616(3) 1.24993(14) 0.07644(8) 0.0363(5) Uani 1 1 d . . . . .
O20 O 0.5273(2) 0.66574(13) 0.19305(7) 0.0185(3) Uani 1 1 d D . . . .
H20A H 0.453(3) 0.664(2) 0.2223(11) 0.028 Uiso 1 1 d D U . . .
H20B H 0.574(3) 0.6031(16) 0.2052(14) 0.028 Uiso 1 1 d D U . . .
O21 O 0.5673(2) 0.58450(14) 0.07341(8) 0.0207(3) Uani 1 1 d . . . . .
H21A H 0.554(4) 0.528(3) 0.0994(15) 0.031 Uiso 1 1 d . U . . .
H21B H 0.668(4) 0.594(3) 0.0784(15) 0.031 Uiso 1 1 d . U . . .
O22 O 0.2250(2) 0.60750(15) 0.12779(8) 0.0246(4) Uani 1 1 d D . . . .
H22A H 0.208(4) 0.580(3) 0.1658(9) 0.037 Uiso 1 1 d D U . . .
H22B H 0.127(3) 0.623(3) 0.1129(14) 0.037 Uiso 1 1 d D U . . .
O24 O 0.8885(2) 0.64939(14) 0.08225(9) 0.0295(4) Uani 1 1 d . . . . .
O25 O 0.9963(2) 0.81081(16) 0.05397(9) 0.0335(4) Uani 1 1 d . . . . .
O26 O 0.72520(19) 0.79634(13) 0.06728(8) 0.0215(3) Uani 1 1 d . . . . .
O28 O 0.5815(2) 0.39286(14) 0.16086(9) 0.0318(4) Uani 1 1 d . . . . .
O29 O 0.7817(2) 0.31052(14) 0.22148(9) 0.0287(4) Uani 1 1 d . . . . .
O30 O 0.6976(3) 0.47342(14) 0.23260(9) 0.0328(4) Uani 1 1 d . . . . .
O42 O 0.0347(2) 0.33608(13) 0.30624(7) 0.0193(3) Uani 1 1 d D . . . .
H42A H 0.080(3) 0.3983(17) 0.2968(14) 0.029 Uiso 1 1 d D U . . .
H42B H -0.037(3) 0.337(2) 0.2773(12) 0.029 Uiso 1 1 d D U . . .
O43 O 0.0549(2) 0.41870(13) 0.42523(8) 0.0204(3) Uani 1 1 d . . . . .
H43A H 0.040(4) 0.475(3) 0.3995(15) 0.031 Uiso 1 1 d . U . . .
H43B H 0.166(4) 0.402(2) 0.4274(14) 0.031 Uiso 1 1 d . U . . .
O44 O -0.2860(2) 0.38908(14) 0.37075(8) 0.0249(3) Uani 1 1 d . . . . .
H44A H -0.281880 0.448871 0.385064 0.037 Uiso 1 1 d R U . . .
H44B H -0.383619 0.369625 0.384854 0.037 Uiso 1 1 d R U . . .
O46 O -0.1314(3) 0.02051(15) 0.20384(8) 0.0310(4) Uani 1 1 d . . . . .
O47 O -0.0951(2) -0.14632(13) 0.26518(8) 0.0237(3) Uani 1 1 d . . . . .
O50 O -0.4289(2) -0.16738(16) 0.32231(9) 0.0323(4) Uani 1 1 d . . . . .
O51 O -0.2925(2) -0.24879(13) 0.41214(8) 0.0293(4) Uani 1 1 d . . . . .
O54 O 0.3807(2) 0.35043(14) 0.42324(10) 0.0321(4) Uani 1 1 d . . . . .
O55 O 0.2279(2) 0.20415(13) 0.43423(8) 0.0230(3) Uani 1 1 d . . . . .
O56 O 0.4941(2) 0.18875(17) 0.45591(10) 0.0370(5) Uani 1 1 d . . . . .
O58 O 0.2002(3) 0.52689(14) 0.26687(9) 0.0331(4) Uani 1 1 d . . . . .
O59 O 0.2705(2) 0.68948(14) 0.27803(9) 0.0300(4) Uani 1 1 d . . . . .
O60 O 0.0670(2) 0.60911(14) 0.33712(9) 0.0301(4) Uani 1 1 d . . . . .
S8 S 0.25579(7) 0.93698(4) -0.06786(2) 0.01856(11) Uani 1 1 d . . . . .
S38 S -0.23357(7) 0.06675(4) 0.56804(2) 0.01727(11) Uani 1 1 d . . . . .
C2 C 0.3850(3) 0.90243(17) 0.17532(10) 0.0152(4) Uani 1 1 d . . . . .
H2 H 0.430840 0.856207 0.212475 0.018 Uiso 1 1 calc R U . . .
C3 C 0.3268(3) 1.00738(17) 0.18058(10) 0.0152(4) Uani 1 1 d . . . . .
C4 C 0.2578(3) 1.07466(17) 0.12653(10) 0.0171(4) Uani 1 1 d . . . . .
C5 C 0.2526(3) 1.03589(17) 0.06831(10) 0.0171(4) Uani 1 1 d . . . . .
H5 H 0.206905 1.080386 0.030503 0.020 Uiso 1 1 calc R U . . .
C6 C 0.3154(3) 0.93107(17) 0.06657(9) 0.0142(4) Uani 1 1 d . . . . .
C7 C 0.3217(3) 0.88125(17) 0.00846(10) 0.0145(4) Uani 1 1 d . . . . .
C9 C 0.3130(3) 0.81726(18) -0.09367(11) 0.0218(4) Uani 1 1 d . . . . .
H9 H 0.301375 0.804941 -0.136848 0.026 Uiso 1 1 calc R U . . .
C10 C 0.3769(3) 0.74288(18) -0.04416(10) 0.0197(4) Uani 1 1 d . . . . .
H10 H 0.415408 0.671558 -0.049058 0.024 Uiso 1 1 calc R U . . .
C12 C 0.3355(3) 1.04172(17) 0.24576(10) 0.0162(4) Uani 1 1 d . . . . .
C15 C 0.4553(3) 1.1648(2) 0.30358(12) 0.0284(5) Uani 1 1 d . . . . .
H15A H 0.550498 1.214760 0.300836 0.043 Uiso 1 1 calc R U . . .
H15B H 0.467245 1.107510 0.342268 0.043 Uiso 1 1 calc R U . . .
H15C H 0.348390 1.205875 0.306472 0.043 Uiso 1 1 calc R U . . .
C16 C 0.1853(3) 1.18556(18) 0.13349(11) 0.0204(4) Uani 1 1 d . . . . .
C19 C 0.0906(5) 1.3583(2) 0.07962(14) 0.0509(9) Uani 1 1 d . . . . .
H19A H 0.058525 1.395353 0.035988 0.076 Uiso 1 1 calc R U . . .
H19B H 0.175500 1.401350 0.096897 0.076 Uiso 1 1 calc R U . . .
H19C H -0.009926 1.351175 0.108137 0.076 Uiso 1 1 calc R U . . .
C32 C -0.0967(3) 0.10057(17) 0.32444(10) 0.0151(4) Uani 1 1 d . . . . .
H32 H -0.044156 0.143982 0.287746 0.018 Uiso 1 1 calc R U . . .
C33 C -0.1571(3) -0.00150(17) 0.31886(10) 0.0152(4) Uani 1 1 d . . . . .
C34 C -0.2383(3) -0.06453(17) 0.37204(10) 0.0159(4) Uani 1 1 d . . . . .
C35 C -0.2463(3) -0.02579(17) 0.43055(10) 0.0162(4) Uani 1 1 d . . . . .
H35 H -0.296826 -0.067984 0.468113 0.019 Uiso 1 1 calc R U . . .
C36 C -0.1791(3) 0.07519(16) 0.43276(9) 0.0136(4) Uani 1 1 d . . . . .
C37 C -0.1747(2) 0.12442(16) 0.49106(9) 0.0134(4) Uani 1 1 d . . . . .
C39 C -0.1813(3) 0.18467(18) 0.59417(10) 0.0203(4) Uani 1 1 d . . . . .
H39 H -0.192333 0.196009 0.637742 0.024 Uiso 1 1 calc R U . . .
C40 C -0.1216(3) 0.25983(18) 0.54378(10) 0.0185(4) Uani 1 1 d . . . . .
H40 H -0.085262 0.330282 0.548668 0.022 Uiso 1 1 calc R U . . .
C45 C -0.1281(3) -0.03938(18) 0.25563(10) 0.0182(4) Uani 1 1 d . . . . .
C48 C -0.0828(4) -0.1944(2) 0.20709(12) 0.0311(6) Uani 1 1 d . . . . .
H48A H 0.023523 -0.172678 0.183900 0.047 Uiso 1 1 calc R U . . .
H48B H -0.179022 -0.168533 0.178935 0.047 Uiso 1 1 calc R U . . .
H48C H -0.084478 -0.274488 0.219147 0.047 Uiso 1 1 calc R U . . .
C49 C -0.3297(3) -0.16605(18) 0.36485(11) 0.0197(4) Uani 1 1 d . . . . .
C52 C -0.3745(5) -0.3513(2) 0.40854(16) 0.0471(8) Uani 1 1 d . . . . .
H52A H -0.339794 -0.375725 0.368196 0.071 Uiso 1 1 calc R U . . .
H52B H -0.498025 -0.339948 0.409237 0.071 Uiso 1 1 calc R U . . .
H52C H -0.340944 -0.407179 0.445769 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 O20 1.9735(15) . ?
Cu1 N11 1.9767(17) . ?
Cu1 O21 1.9993(17) . ?
Cu1 N1 2.0393(18) . ?
Cu1 O22 2.2530(17) . ?
Cu2 O42 1.9697(15) . ?
Cu2 N41 1.9732(17) . ?
Cu2 O43 1.9930(16) . ?
Cu2 N31 2.0321(17) . ?
Cu2 O44 2.2658(16) . ?
N1 C2 1.339(3) . ?
N1 C6 1.349(3) . ?
N11 C7 1.319(3) . ?
N11 C10 1.374(3) . ?
N23 O25 1.235(3) . ?
N23 O26 1.248(2) . ?
N23 O24 1.278(3) . ?
N27 O28 1.243(3) . ?
N27 O29 1.246(2) . ?
N27 O30 1.261(3) . ?
N31 C32 1.339(3) . ?
N31 C36 1.356(2) . ?
N41 C37 1.314(3) . ?
N41 C40 1.371(3) . ?
N53 O56 1.233(3) . ?
N53 O55 1.241(2) . ?
N53 O54 1.280(3) . ?
N57 O60 1.244(3) . ?
N57 O59 1.246(2) . ?
N57 O58 1.260(3) . ?
O13 C12 1.201(3) . ?
O14 C12 1.324(3) . ?
O14 C15 1.452(3) . ?
O17 C16 1.194(3) . ?
O18 C16 1.325(3) . ?
O18 C19 1.454(3) . ?
O20 H20A 0.840(17) . ?
O20 H20B 0.847(17) . ?
O21 H21A 0.82(3) . ?
O21 H21B 0.82(3) . ?
O22 H22A 0.818(17) . ?
O22 H22B 0.839(17) . ?
O42 H42A 0.849(17) . ?
O42 H42B 0.833(17) . ?
O43 H43A 0.81(3) . ?
O43 H43B 0.89(3) . ?
O44 H44A 0.8500 . ?
O44 H44B 0.8444 . ?
O46 C45 1.199(3) . ?
O47 C45 1.324(3) . ?
O47 C48 1.449(3) . ?
O50 C49 1.198(3) . ?
O51 C49 1.322(3) . ?
O51 C52 1.455(3) . ?
S8 C7 1.706(2) . ?
S8 C9 1.716(2) . ?
S38 C37 1.703(2) . ?
S38 C39 1.714(2) . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(3) . ?
C3 C12 1.504(3) . ?
C4 C5 1.390(3) . ?
C4 C16 1.506(3) . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.460(3) . ?
C9 C10 1.352(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C32 C33 1.389(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.395(3) . ?
C33 C45 1.495(3) . ?
C34 C35 1.394(3) . ?
C34 C49 1.499(3) . ?
C35 C36 1.381(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.461(3) . ?
C39 C40 1.361(3) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O20 Cu1 N11 173.03(7) . . ?
O20 Cu1 O21 92.64(7) . . ?
N11 Cu1 O21 93.21(7) . . ?
O20 Cu1 N1 92.27(7) . . ?
N11 Cu1 N1 81.22(7) . . ?
O21 Cu1 N1 166.87(7) . . ?
O20 Cu1 O22 87.81(6) . . ?
N11 Cu1 O22 96.25(7) . . ?
O21 Cu1 O22 87.14(7) . . ?
N1 Cu1 O22 105.21(7) . . ?
O42 Cu2 N41 173.28(7) . . ?
O42 Cu2 O43 92.74(7) . . ?
N41 Cu2 O43 92.95(7) . . ?
O42 Cu2 N31 92.41(7) . . ?
N41 Cu2 N31 81.35(7) . . ?
O43 Cu2 N31 168.35(7) . . ?
O42 Cu2 O44 88.36(6) . . ?
N41 Cu2 O44 95.29(7) . . ?
O43 Cu2 O44 89.12(7) . . ?
N31 Cu2 O44 101.47(7) . . ?
C2 N1 C6 118.80(18) . . ?
C2 N1 Cu1 127.74(14) . . ?
C6 N1 Cu1 113.46(14) . . ?
C7 N11 C10 111.79(17) . . ?
C7 N11 Cu1 113.97(14) . . ?
C10 N11 Cu1 134.23(15) . . ?
O25 N23 O26 120.8(2) . . ?
O25 N23 O24 119.8(2) . . ?
O26 N23 O24 119.47(19) . . ?
O28 N27 O29 120.3(2) . . ?
O28 N27 O30 120.60(19) . . ?
O29 N27 O30 119.08(19) . . ?
C32 N31 C36 118.52(18) . . ?
C32 N31 Cu2 128.13(14) . . ?
C36 N31 Cu2 113.33(14) . . ?
C37 N41 C40 111.68(17) . . ?
C37 N41 Cu2 114.08(14) . . ?
C40 N41 Cu2 134.21(15) . . ?
O56 N53 O55 120.7(2) . . ?
O56 N53 O54 119.6(2) . . ?
O55 N53 O54 119.63(19) . . ?
O60 N57 O59 120.3(2) . . ?
O60 N57 O58 120.71(19) . . ?
O59 N57 O58 118.94(19) . . ?
C12 O14 C15 114.75(17) . . ?
C16 O18 C19 114.86(19) . . ?
Cu1 O20 H20A 117(2) . . ?
Cu1 O20 H20B 121(2) . . ?
H20A O20 H20B 99(3) . . ?
Cu1 O21 H21A 112(2) . . ?
Cu1 O21 H21B 103(2) . . ?
H21A O21 H21B 100(3) . . ?
Cu1 O22 H22A 119(2) . . ?
Cu1 O22 H22B 125(2) . . ?
H22A O22 H22B 104(3) . . ?
Cu2 O42 H42A 117(2) . . ?
Cu2 O42 H42B 117(2) . . ?
H42A O42 H42B 104(3) . . ?
Cu2 O43 H43A 113(2) . . ?
Cu2 O43 H43B 103(2) . . ?
H43A O43 H43B 109(3) . . ?
Cu2 O44 H44A 109.4 . . ?
Cu2 O44 H44B 124.5 . . ?
H44A O44 H44B 98.7 . . ?
C45 O47 C48 115.62(18) . . ?
C49 O51 C52 115.3(2) . . ?
C7 S8 C9 89.71(11) . . ?
C37 S38 C39 89.63(10) . . ?
N1 C2 C3 122.00(18) . . ?
N1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C4 C3 C2 119.12(19) . . ?
C4 C3 C12 122.63(19) . . ?
C2 C3 C12 118.20(18) . . ?
C5 C4 C3 118.90(19) . . ?
C5 C4 C16 122.12(19) . . ?
C3 C4 C16 118.94(19) . . ?
C6 C5 C4 118.65(19) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
N1 C6 C5 122.48(19) . . ?
N1 C6 C7 113.17(17) . . ?
C5 C6 C7 124.35(18) . . ?
N11 C7 C6 118.14(17) . . ?
N11 C7 S8 113.75(15) . . ?
C6 C7 S8 128.09(15) . . ?
C10 C9 S8 110.72(17) . . ?
C10 C9 H9 124.6 . . ?
S8 C9 H9 124.6 . . ?
C9 C10 N11 114.0(2) . . ?
C9 C10 H10 123.0 . . ?
N11 C10 H10 123.0 . . ?
O13 C12 O14 126.4(2) . . ?
O13 C12 C3 122.49(19) . . ?
O14 C12 C3 111.10(17) . . ?
O14 C15 H15A 109.5 . . ?
O14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O17 C16 O18 124.8(2) . . ?
O17 C16 C4 123.2(2) . . ?
O18 C16 C4 112.00(19) . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N31 C32 C33 122.02(18) . . ?
N31 C32 H32 119.0 . . ?
C33 C32 H32 119.0 . . ?
C32 C33 C34 119.31(19) . . ?
C32 C33 C45 117.59(18) . . ?
C34 C33 C45 123.08(19) . . ?
C35 C34 C33 118.57(19) . . ?
C35 C34 C49 120.43(18) . . ?
C33 C34 C49 120.73(19) . . ?
C36 C35 C34 118.63(18) . . ?
C36 C35 H35 120.7 . . ?
C34 C35 H35 120.7 . . ?
N31 C36 C35 122.73(19) . . ?
N31 C36 C37 112.81(17) . . ?
C35 C36 C37 124.46(18) . . ?
N41 C37 C36 118.16(17) . . ?
N41 C37 S38 114.26(15) . . ?
C36 C37 S38 127.58(15) . . ?
C40 C39 S38 110.53(17) . . ?
C40 C39 H39 124.7 . . ?
S38 C39 H39 124.7 . . ?
C39 C40 N41 113.9(2) . . ?
C39 C40 H40 123.0 . . ?
N41 C40 H40 123.0 . . ?
O46 C45 O47 125.4(2) . . ?
O46 C45 C33 123.8(2) . . ?
O47 C45 C33 110.75(17) . . ?
O47 C48 H48A 109.5 . . ?
O47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
O47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
O50 C49 O51 125.9(2) . . ?
O50 C49 C34 122.4(2) . . ?
O51 C49 C34 111.64(19) . . ?
O51 C52 H52A 109.5 . . ?
O51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
O51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?

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
C6 N1 C2 C3 1.0(3) . . . . ?
Cu1 N1 C2 C3 -178.95(15) . . . . ?
N1 C2 C3 C4 0.8(3) . . . . ?
N1 C2 C3 C12 178.49(18) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
C12 C3 C4 C5 -179.13(19) . . . . ?
C2 C3 C4 C16 176.31(19) . . . . ?
C12 C3 C4 C16 -1.3(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C16 C4 C5 C6 -177.2(2) . . . . ?
C2 N1 C6 C5 -2.1(3) . . . . ?
Cu1 N1 C6 C5 177.87(16) . . . . ?
C2 N1 C6 C7 177.66(18) . . . . ?
Cu1 N1 C6 C7 -2.4(2) . . . . ?
C4 C5 C6 N1 1.3(3) . . . . ?
C4 C5 C6 C7 -178.40(19) . . . . ?
C10 N11 C7 C6 178.97(18) . . . . ?
Cu1 N11 C7 C6 -0.3(2) . . . . ?
C10 N11 C7 S8 0.5(2) . . . . ?
Cu1 N11 C7 S8 -178.75(9) . . . . ?
N1 C6 C7 N11 1.8(3) . . . . ?
C5 C6 C7 N11 -178.4(2) . . . . ?
N1 C6 C7 S8 -179.97(15) . . . . ?
C5 C6 C7 S8 -0.2(3) . . . . ?
C9 S8 C7 N11 -0.44(17) . . . . ?
C9 S8 C7 C6 -178.7(2) . . . . ?
C7 S8 C9 C10 0.26(19) . . . . ?
S8 C9 C10 N11 0.0(3) . . . . ?
C7 N11 C10 C9 -0.3(3) . . . . ?
Cu1 N11 C10 C9 178.74(16) . . . . ?
C15 O14 C12 O13 -10.6(3) . . . . ?
C15 O14 C12 C3 171.03(18) . . . . ?
C4 C3 C12 O13 107.5(3) . . . . ?
C2 C3 C12 O13 -70.1(3) . . . . ?
C4 C3 C12 O14 -74.1(3) . . . . ?
C2 C3 C12 O14 108.3(2) . . . . ?
C19 O18 C16 O17 0.3(4) . . . . ?
C19 O18 C16 C4 179.6(2) . . . . ?
C5 C4 C16 O17 162.1(2) . . . . ?
C3 C4 C16 O17 -15.6(3) . . . . ?
C5 C4 C16 O18 -17.2(3) . . . . ?
C3 C4 C16 O18 165.0(2) . . . . ?
C36 N31 C32 C33 2.6(3) . . . . ?
Cu2 N31 C32 C33 -175.85(15) . . . . ?
N31 C32 C33 C34 1.6(3) . . . . ?
N31 C32 C33 C45 -177.15(18) . . . . ?
C32 C33 C34 C35 -4.1(3) . . . . ?
C45 C33 C34 C35 174.60(19) . . . . ?
C32 C33 C34 C49 170.00(19) . . . . ?
C45 C33 C34 C49 -11.3(3) . . . . ?
C33 C34 C35 C36 2.4(3) . . . . ?
C49 C34 C35 C36 -171.73(19) . . . . ?
C32 N31 C36 C35 -4.5(3) . . . . ?
Cu2 N31 C36 C35 174.22(16) . . . . ?
C32 N31 C36 C37 175.75(17) . . . . ?
Cu2 N31 C36 C37 -5.6(2) . . . . ?
C34 C35 C36 N31 1.9(3) . . . . ?
C34 C35 C36 C37 -178.31(19) . . . . ?
C40 N41 C37 C36 -179.87(18) . . . . ?
Cu2 N41 C37 C36 -1.6(2) . . . . ?
C40 N41 C37 S38 -0.2(2) . . . . ?
Cu2 N41 C37 S38 178.13(9) . . . . ?
N31 C36 C37 N41 4.9(3) . . . . ?
C35 C36 C37 N41 -174.91(19) . . . . ?
N31 C36 C37 S38 -174.82(15) . . . . ?
C35 C36 C37 S38 5.4(3) . . . . ?
C39 S38 C37 N41 0.36(17) . . . . ?
C39 S38 C37 C36 -179.95(19) . . . . ?
C37 S38 C39 C40 -0.47(18) . . . . ?
S38 C39 C40 N41 0.5(3) . . . . ?
C37 N41 C40 C39 -0.2(3) . . . . ?
Cu2 N41 C40 C39 -178.04(16) . . . . ?
C48 O47 C45 O46 -7.8(3) . . . . ?
C48 O47 C45 C33 173.62(19) . . . . ?
C32 C33 C45 O46 -35.6(3) . . . . ?
C34 C33 C45 O46 145.7(2) . . . . ?
C32 C33 C45 O47 142.95(19) . . . . ?
C34 C33 C45 O47 -35.8(3) . . . . ?
C52 O51 C49 O50 3.7(4) . . . . ?
C52 O51 C49 C34 -179.3(2) . . . . ?
C35 C34 C49 O50 125.4(2) . . . . ?
C33 C34 C49 O50 -48.6(3) . . . . ?
C35 C34 C49 O51 -51.7(3) . . . . ?
C33 C34 C49 O51 134.3(2) . . . . ?

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
#O20 H20A N57  0.840(17) 2.647(19) 3.452(3) 161(3) . yes
#O22 H22B N23  0.839(17) 2.64(2) 3.422(3) 155(3) 1_455 yes
#O22 H22B O25  0.839(17) 2.63(3) 3.231(3) 130(3) 1_455 yes
#O42 H42B N27  0.833(17) 2.685(19) 3.481(3) 160(3) 1_455 yes
#O44 H44B O56  0.84 2.65 3.297(3) 134.3 1_455 yes
#C2 H2 O59  0.95 2.61 3.228(3) 123.1 . yes
#C5 H5 N23  0.95 2.70 3.624(3) 165.0 2_675 yes
#C10 H10 O28  0.95 2.61 3.216(3) 122.3 2_665 yes
#C19 H19A O24  0.98 2.66 3.409(4) 133.7 2_675 yes
#C32 H32 O17  0.95 2.65 3.572(3) 163.2 1_545 yes
#C32 H32 O29  0.95 2.64 3.203(3) 118.6 1_455 yes
#C40 H40 O60  0.95 2.64 3.253(3) 122.7 2_566 yes
O20 H20A O59 0.840(17) 1.890(18) 2.717(2) 168(3) . yes
O20 H20B O30 0.847(17) 1.864(18) 2.707(2) 174(3) . yes
O21 H21A O28 0.82(3) 1.93(3) 2.726(2) 166(3) . yes
O21 H21B N23 0.82(3) 2.55(3) 3.206(3) 139(3) . yes
O21 H21B O24 0.82(3) 1.89(3) 2.696(3) 167(3) . yes
O21 H21B O26 0.82(3) 2.53(3) 2.917(2) 111(3) . yes
O22 H22A O58 0.818(17) 2.100(19) 2.908(2) 169(3) . yes
O22 H22B O24 0.839(17) 2.000(18) 2.837(2) 176(3) 1_455 yes
O42 H42A O58 0.849(17) 1.878(18) 2.720(2) 172(3) . yes
O42 H42B O29 0.833(17) 1.935(18) 2.755(2) 168(3) 1_455 yes
O43 H43A O60 0.81(3) 1.93(3) 2.724(2) 165(3) . yes
O43 H43B N53 0.89(3) 2.45(3) 3.203(3) 142(3) . yes
O43 H43B O54 0.89(3) 1.80(3) 2.684(2) 170(3) . yes
O43 H43B O55 0.89(3) 2.47(3) 2.934(2) 113(2) . yes
O44 H44B N53 0.84 2.62 3.434(3) 160.8 1_455 yes
O44 H44B O54 0.84 2.01 2.848(2) 169.5 1_455 yes
C2 H2 O20 0.95 2.56 3.076(3) 114.2 . yes
C2 H2 O50 0.95 2.53 3.391(3) 150.1 1_665 yes
C5 H5 O25 0.95 2.58 3.499(3) 163.7 2_675 yes
C5 H5 O26 0.95 2.39 3.207(3) 144.6 2_675 yes
C9 H9 O29 0.95 2.57 3.449(3) 153.2 2_665 yes
C15 H15A O29 0.98 2.60 3.436(3) 142.7 1_565 yes
C32 H32 O42 0.95 2.57 3.081(3) 113.6 . yes
C35 H35 O55 0.95 2.46 3.266(3) 142.1 2_556 yes
C35 H35 O56 0.95 2.52 3.444(3) 163.3 2_556 yes
C39 H39 O59 0.95 2.52 3.387(3) 152.7 2_566 yes
C48 H48B O26 0.98 2.58 3.341(3) 134.2 1_445 yes

_refine_diff_density_max         1.135
_refine_diff_density_min         -0.872
_refine_diff_density_rms         0.089

