# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1965451'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2019-11-13 deposited with the CCDC.	2022-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H25 Cu N5 O5, 2(Cl O4)'
_chemical_formula_sum            'C18 H25 Cl2 Cu N5 O13'
_chemical_formula_weight         653.87

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'

_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                   9.7716(4)
_cell_length_b                   11.9652(4)
_cell_length_c                   12.2930(6)
_cell_angle_alpha                80.798(3)
_cell_angle_beta                 68.698(4)
_cell_angle_gamma                84.505(3)
_cell_volume                     1320.75(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    10512
_cell_measurement_theta_min      1.7300
_cell_measurement_theta_max      27.3150

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_F_000             670
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.102
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.38204
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      295(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 16.0593
_diffrn_reflns_number            22490
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_av_R_equivalents  0.0990
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.726
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4658
_reflns_number_gt                4241
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'

_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)+(0.0900P)²+19.3000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     .
_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         4658
_refine_ls_number_parameters     357
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1377
_refine_ls_R_factor_gt           0.1325
_refine_ls_wR_factor_ref         0.3104
_refine_ls_wR_factor_gt          0.3081
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.58613(15) 0.76976(10) 0.24443(12) 0.0519(4) Uani 1 1 d . . . . .
O1 O 0.3023(9) 0.7164(7) 0.2397(8) 0.065(2) Uani 1 1 d . . . . .
N2 N 0.4502(10) 0.6812(7) 0.2112(8) 0.055(2) Uani 1 1 d . . . . .
C3 C 0.4633(13) 0.5787(9) 0.1778(9) 0.055(3) Uani 1 1 d . . . . .
C4 C 0.3237(14) 0.5463(10) 0.1855(11) 0.065(3) Uani 1 1 d . . . . .
H4 H 0.3016 0.4787 0.1686 0.078 Uiso 1 1 calc R U . . .
C5 C 0.2316(14) 0.6325(9) 0.2216(11) 0.063(3) Uani 1 1 d . . . . .
C51 C 0.0680(16) 0.6539(14) 0.2517(17) 0.097(5) Uani 1 1 d . . . . .
H51A H 0.0501 0.7202 0.2027 0.145 Uiso 1 1 calc R U . . .
H51B H 0.0232 0.6653 0.3330 0.145 Uiso 1 1 calc R U . . .
H51C H 0.0268 0.5898 0.2387 0.145 Uiso 1 1 calc R U . . .
N6 N 0.5909(11) 0.5175(7) 0.1441(9) 0.062(2) Uani 1 1 d . . . . .
H6 H 0.5938 0.4587 0.1110 0.075 Uiso 1 1 calc R U . . .
C7 C 0.7224(13) 0.5432(9) 0.1595(11) 0.061(3) Uani 1 1 d . . . . .
H7 H 0.8003 0.4879 0.1243 0.074 Uiso 1 1 calc R U . . .
O7 O 0.7691(9) 0.6529(7) 0.1036(7) 0.068(2) Uani 1 1 d . . . . .
C71 C 0.811(2) 0.6700(15) -0.0231(12) 0.107(6) Uani 1 1 d . . . . .
H71A H 0.9007 0.6272 -0.0573 0.161 Uiso 1 1 calc R U . . .
H71B H 0.8256 0.7491 -0.0518 0.161 Uiso 1 1 calc R U . . .
H71C H 0.7347 0.6452 -0.0443 0.161 Uiso 1 1 calc R U . . .
C8 C 0.7076(11) 0.5403(8) 0.2852(10) 0.051(2) Uani 1 1 d . . . . .
N9 N 0.6440(9) 0.6331(6) 0.3370(7) 0.0471(19) Uani 1 1 d . . . . .
C10 C 0.6284(11) 0.6363(8) 0.4493(9) 0.050(2) Uani 1 1 d . . . . .
C11 C 0.6777(13) 0.5462(9) 0.5124(10) 0.060(3) Uani 1 1 d . . . . .
H11 H 0.6692 0.5503 0.5895 0.072 Uiso 1 1 calc R U . . .
C12 C 0.7385(14) 0.4519(10) 0.4625(13) 0.072(4) Uani 1 1 d . . . . .
H12 H 0.7704 0.3907 0.5055 0.086 Uiso 1 1 calc R U . . .
C13 C 0.7528(13) 0.4471(9) 0.3481(12) 0.064(3) Uani 1 1 d . . . . .
H13 H 0.7924 0.3821 0.3134 0.077 Uiso 1 1 calc R U . . .
C14 C 0.5572(12) 0.7439(9) 0.5005(9) 0.053(3) Uani 1 1 d . . . . .
H14 H 0.5064 0.7252 0.5856 0.064 Uiso 1 1 calc R U . . .
O14 O 0.4540(8) 0.7823(6) 0.4483(6) 0.0552(18) Uani 1 1 d . . . . .
C141 C 0.3617(16) 0.8769(12) 0.4947(15) 0.091(5) Uani 1 1 d . . . . .
H14A H 0.3072 0.8562 0.5770 0.137 Uiso 1 1 calc R U . . .
H14B H 0.2946 0.8983 0.4533 0.137 Uiso 1 1 calc R U . . .
H14C H 0.4214 0.9396 0.4849 0.137 Uiso 1 1 calc R U . . .
N15 N 0.6661(10) 0.8284(7) 0.4796(8) 0.056(2) Uani 1 1 d . . . . .
H15 H 0.6753 0.8521 0.5389 0.067 Uiso 1 1 calc R U . . .
C16 C 0.7530(11) 0.8704(7) 0.3690(10) 0.048(2) Uani 1 1 d . . . . .
N17 N 0.7281(9) 0.8550(7) 0.2754(7) 0.049(2) Uani 1 1 d . . . . .
O18 O 0.8368(8) 0.9137(6) 0.1777(6) 0.0556(18) Uani 1 1 d . . . . .
C19 C 0.9215(12) 0.9623(8) 0.2208(10) 0.053(2) Uani 1 1 d . . . . .
C191 C 1.0416(16) 1.0307(12) 0.1335(12) 0.083(4) Uani 1 1 d . . . . .
H19A H 1.0009 1.0999 0.1038 0.125 Uiso 1 1 calc R U . . .
H19B H 1.0950 0.9886 0.0695 0.125 Uiso 1 1 calc R U . . .
H19C H 1.1070 1.0480 0.1703 0.125 Uiso 1 1 calc R U . . .
C20 C 0.8760(12) 0.9396(9) 0.3380(10) 0.055(3) Uani 1 1 d . . . . .
H20 H 0.9156 0.9636 0.3882 0.066 Uiso 1 1 calc R U . . .
O1A O 0.5337(13) 0.9115(8) 0.1621(11) 0.104(4) Uani 1 1 d . . . . .
H1A H 0.6128 0.9573 0.1200 0.125 Uiso 1 1 calc R U . . .
C1A C 0.394(3) 0.959(2) 0.154(3) 0.187(14) Uani 1 1 d . . . . .
H1A1 H 0.3708 0.9224 0.0993 0.281 Uiso 1 1 calc R U . . .
H1A2 H 0.4015 1.0385 0.1280 0.281 Uiso 1 1 calc R U . . .
H1A3 H 0.3182 0.9459 0.2304 0.281 Uiso 1 1 calc R U . . .
Cl1B Cl 0.9234(4) 0.7628(3) 0.6297(3) 0.0683(8) Uani 1 1 d . . . . .
O1B O 0.848(3) 0.6779(19) 0.657(3) 0.291(15) Uani 1 1 d . . . . .
O2B O 1.006(2) 0.754(2) 0.5186(13) 0.235(13) Uani 1 1 d . . . . .
O3B O 0.8253(18) 0.8592(12) 0.6356(13) 0.150(6) Uani 1 1 d . . . . .
O4B O 0.9956(16) 0.7571(14) 0.7027(12) 0.143(6) Uani 1 1 d . . . . .
Cl1C Cl 0.6484(5) 0.2111(3) 0.1260(4) 0.0895(11) Uani 1 1 d . . . . .
O1C O 0.751(3) 0.2675(15) 0.140(3) 0.283(17) Uani 1 1 d . . . . .
O2C O 0.705(3) 0.1465(18) 0.0380(18) 0.245(12) Uani 1 1 d . . . . .
O3C O 0.591(2) 0.1301(15) 0.2257(15) 0.170(7) Uani 1 1 d . . . . .
O4C O 0.5403(17) 0.2870(11) 0.1040(15) 0.137(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1A 1.956(9) . ?
Cu1 N2 1.964(8) . ?
Cu1 N17 1.971(8) . ?
Cu1 N9 1.996(8) . ?
Cu1 O14 2.388(7) . ?
O1 C5 1.360(13) . ?
O1 N2 1.397(12) . ?
N2 C3 1.335(13) . ?
C3 N6 1.346(15) . ?
C3 C4 1.420(15) . ?
C4 C5 1.322(17) . ?
C4 H4 0.9300 . ?
C5 C51 1.510(18) . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
N6 C7 1.433(15) . ?
N6 H6 0.8600 . ?
C7 O7 1.414(13) . ?
C7 C8 1.493(16) . ?
C7 H7 0.9800 . ?
O7 C71 1.444(15) . ?
C71 H71A 0.9600 . ?
C71 H71B 0.9600 . ?
C71 H71C 0.9600 . ?
C8 N9 1.354(12) . ?
C8 C13 1.384(15) . ?
N9 C10 1.339(13) . ?
C10 C11 1.378(15) . ?
C10 C14 1.519(14) . ?
C11 C12 1.353(18) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(19) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 O14 1.389(13) . ?
C14 N15 1.464(13) . ?
C14 H14 0.9800 . ?
O14 C141 1.434(13) . ?
C141 H14A 0.9600 . ?
C141 H14B 0.9600 . ?
C141 H14C 0.9600 . ?
N15 C16 1.359(13) . ?
N15 H15 0.8600 . ?
C16 N17 1.303(13) . ?
C16 C20 1.426(14) . ?
N17 O18 1.417(10) . ?
O18 C19 1.347(12) . ?
C19 C20 1.333(15) . ?
C19 C191 1.479(15) . ?
C191 H19A 0.9600 . ?
C191 H19B 0.9600 . ?
C191 H19C 0.9600 . ?
C20 H20 0.9300 . ?
O1A C1A 1.45(2) . ?
O1A H1A 0.9300 . ?
C1A H1A1 0.9600 . ?
C1A H1A2 0.9600 . ?
C1A H1A3 0.9600 . ?
Cl1B O1B 1.240(16) . ?
Cl1B O4B 1.319(12) . ?
Cl1B O2B 1.323(15) . ?
Cl1B O3B 1.421(11) . ?
Cl1C O1C 1.339(16) . ?
Cl1C O2C 1.350(15) . ?
Cl1C O4C 1.400(13) . ?
Cl1C O3C 1.407(15) . ?

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
O1A Cu1 N2 93.6(4) . . ?
O1A Cu1 N17 87.6(4) . . ?
N2 Cu1 N17 178.0(4) . . ?
O1A Cu1 N9 175.1(4) . . ?
N2 Cu1 N9 90.8(3) . . ?
N17 Cu1 N9 88.2(3) . . ?
O1A Cu1 O14 104.6(4) . . ?
N2 Cu1 O14 99.9(3) . . ?
N17 Cu1 O14 81.3(3) . . ?
N9 Cu1 O14 72.4(3) . . ?
C5 O1 N2 107.3(8) . . ?
C3 N2 O1 106.7(8) . . ?
C3 N2 Cu1 132.5(8) . . ?
O1 N2 Cu1 120.3(6) . . ?
N2 C3 N6 123.7(10) . . ?
N2 C3 C4 109.5(11) . . ?
N6 C3 C4 126.8(10) . . ?
C5 C4 C3 105.6(10) . . ?
C5 C4 H4 127.2 . . ?
C3 C4 H4 127.2 . . ?
C4 C5 O1 110.9(11) . . ?
C4 C5 C51 134.0(11) . . ?
O1 C5 C51 115.0(11) . . ?
C5 C51 H51A 109.5 . . ?
C5 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C5 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C3 N6 C7 124.6(9) . . ?
C3 N6 H6 117.7 . . ?
C7 N6 H6 117.7 . . ?
O7 C7 N6 111.8(10) . . ?
O7 C7 C8 105.8(8) . . ?
N6 C7 C8 114.1(9) . . ?
O7 C7 H7 108.3 . . ?
N6 C7 H7 108.3 . . ?
C8 C7 H7 108.3 . . ?
C7 O7 C71 115.4(10) . . ?
O7 C71 H71A 109.5 . . ?
O7 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
O7 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
N9 C8 C13 120.7(11) . . ?
N9 C8 C7 116.8(9) . . ?
C13 C8 C7 122.6(10) . . ?
C10 N9 C8 119.8(9) . . ?
C10 N9 Cu1 119.5(6) . . ?
C8 N9 Cu1 120.6(7) . . ?
N9 C10 C11 120.6(10) . . ?
N9 C10 C14 116.5(9) . . ?
C11 C10 C14 123.0(10) . . ?
C12 C11 C10 120.3(12) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 119.6(11) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C8 119.1(11) . . ?
C12 C13 H13 120.5 . . ?
C8 C13 H13 120.5 . . ?
O14 C14 N15 112.3(9) . . ?
O14 C14 C10 106.0(8) . . ?
N15 C14 C10 111.7(9) . . ?
O14 C14 H14 108.9 . . ?
N15 C14 H14 108.9 . . ?
C10 C14 H14 108.9 . . ?
C14 O14 C141 115.0(9) . . ?
C14 O14 Cu1 103.2(5) . . ?
C141 O14 Cu1 125.5(9) . . ?
O14 C141 H14A 109.5 . . ?
O14 C141 H14B 109.5 . . ?
H14A C141 H14B 109.5 . . ?
O14 C141 H14C 109.5 . . ?
H14A C141 H14C 109.5 . . ?
H14B C141 H14C 109.5 . . ?
C16 N15 C14 121.8(8) . . ?
C16 N15 H15 119.1 . . ?
C14 N15 H15 119.1 . . ?
N17 C16 N15 122.5(9) . . ?
N17 C16 C20 110.7(9) . . ?
N15 C16 C20 126.7(10) . . ?
C16 N17 O18 106.6(7) . . ?
C16 N17 Cu1 135.2(7) . . ?
O18 N17 Cu1 118.2(6) . . ?
C19 O18 N17 107.0(7) . . ?
C20 C19 O18 111.2(9) . . ?
C20 C19 C191 132.6(11) . . ?
O18 C19 C191 116.3(10) . . ?
C19 C191 H19A 109.5 . . ?
C19 C191 H19B 109.5 . . ?
H19A C191 H19B 109.5 . . ?
C19 C191 H19C 109.5 . . ?
H19A C191 H19C 109.5 . . ?
H19B C191 H19C 109.5 . . ?
C19 C20 C16 104.6(10) . . ?
C19 C20 H20 127.7 . . ?
C16 C20 H20 127.7 . . ?
C1A O1A Cu1 132.0(13) . . ?
C1A O1A H1A 114.0 . . ?
Cu1 O1A H1A 114.0 . . ?
O1A C1A H1A1 109.5 . . ?
O1A C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 109.5 . . ?
O1A C1A H1A3 109.5 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?
O1B Cl1B O4B 108.5(17) . . ?
O1B Cl1B O2B 101.8(19) . . ?
O4B Cl1B O2B 115.4(12) . . ?
O1B Cl1B O3B 107.1(17) . . ?
O4B Cl1B O3B 113.1(8) . . ?
O2B Cl1B O3B 110.1(10) . . ?
O1C Cl1C O2C 113(2) . . ?
O1C Cl1C O4C 110.2(10) . . ?
O2C Cl1C O4C 109.4(13) . . ?
O1C Cl1C O3C 109.0(16) . . ?
O2C Cl1C O3C 102.6(14) . . ?
O4C Cl1C O3C 113.0(11) . . ?

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
C5 O1 N2 C3 -0.1(12) . . . . ?
C5 O1 N2 Cu1 -172.1(7) . . . . ?
O1 N2 C3 N6 -179.7(10) . . . . ?
Cu1 N2 C3 N6 -9.1(17) . . . . ?
O1 N2 C3 C4 -0.6(12) . . . . ?
Cu1 N2 C3 C4 170.0(8) . . . . ?
N2 C3 C4 C5 1.1(14) . . . . ?
N6 C3 C4 C5 -179.8(12) . . . . ?
C3 C4 C5 O1 -1.2(14) . . . . ?
C3 C4 C5 C51 -177.7(15) . . . . ?
N2 O1 C5 C4 0.9(13) . . . . ?
N2 O1 C5 C51 178.1(11) . . . . ?
N2 C3 N6 C7 11.9(17) . . . . ?
C4 C3 N6 C7 -167.1(11) . . . . ?
C3 N6 C7 O7 -58.0(14) . . . . ?
C3 N6 C7 C8 61.9(14) . . . . ?
N6 C7 O7 C71 -63.8(14) . . . . ?
C8 C7 O7 C71 171.5(12) . . . . ?
O7 C7 C8 N9 42.5(12) . . . . ?
N6 C7 C8 N9 -80.8(11) . . . . ?
O7 C7 C8 C13 -138.9(10) . . . . ?
N6 C7 C8 C13 97.8(12) . . . . ?
C13 C8 N9 C10 1.9(14) . . . . ?
C7 C8 N9 C10 -179.5(9) . . . . ?
C13 C8 N9 Cu1 177.5(8) . . . . ?
C7 C8 N9 Cu1 -3.8(12) . . . . ?
C8 N9 C10 C11 0.6(14) . . . . ?
Cu1 N9 C10 C11 -175.1(7) . . . . ?
C8 N9 C10 C14 179.5(8) . . . . ?
Cu1 N9 C10 C14 3.8(12) . . . . ?
N9 C10 C11 C12 -2.1(16) . . . . ?
C14 C10 C11 C12 179.1(10) . . . . ?
C10 C11 C12 C13 1.0(17) . . . . ?
C11 C12 C13 C8 1.5(17) . . . . ?
N9 C8 C13 C12 -2.9(16) . . . . ?
C7 C8 C13 C12 178.5(10) . . . . ?
N9 C10 C14 O14 34.1(12) . . . . ?
C11 C10 C14 O14 -147.1(10) . . . . ?
N9 C10 C14 N15 -88.5(11) . . . . ?
C11 C10 C14 N15 90.3(12) . . . . ?
N15 C14 O14 C141 -64.7(12) . . . . ?
C10 C14 O14 C141 173.2(10) . . . . ?
N15 C14 O14 Cu1 75.5(8) . . . . ?
C10 C14 O14 Cu1 -46.7(8) . . . . ?
O14 C14 N15 C16 -59.1(12) . . . . ?
C10 C14 N15 C16 59.7(13) . . . . ?
C14 N15 C16 N17 12.9(15) . . . . ?
C14 N15 C16 C20 -170.3(10) . . . . ?
N15 C16 N17 O18 177.9(9) . . . . ?
C20 C16 N17 O18 0.6(11) . . . . ?
N15 C16 N17 Cu1 -4.4(16) . . . . ?
C20 C16 N17 Cu1 178.3(8) . . . . ?
C16 N17 O18 C19 -0.4(10) . . . . ?
Cu1 N17 O18 C19 -178.6(7) . . . . ?
N17 O18 C19 C20 0.0(11) . . . . ?
N17 O18 C19 C191 -178.8(10) . . . . ?
O18 C19 C20 C16 0.3(12) . . . . ?
C191 C19 C20 C16 178.9(13) . . . . ?
N17 C16 C20 C19 -0.6(12) . . . . ?
N15 C16 C20 C19 -177.8(10) . . . . ?

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
N6 H6 O4C 0.86 2.19 2.995(16) 155.5 .
C13 H13 O4B 0.93 2.50 3.259(16) 138.9 2_766
N15 H15 O3B 0.86 2.21 2.956(16) 144.8 .
O1A H1A O18 0.93 2.52 3.040(13) 115.4 .
O1A H1A O2C 0.93 2.44 3.27(3) 149.0 1_565
C1A H1A1 O2C 0.96 2.35 3.31(4) 173.0 2_665

_refine_diff_density_max         2.218
_refine_diff_density_min         -1.127
_refine_diff_density_rms         0.159



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

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2150965'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2022-02-08 deposited with the CCDC.	2022-06-22 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         'C18 H25 Cu N5 O5, 2(Cl O4)'
_chemical_formula_sum            'C18 H25 Cl2 Cu N5 O13'
_chemical_formula_weight         653.87

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'

_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                   9.6287(4)
_cell_length_b                   11.9833(5)
_cell_length_c                   12.0249(5)
_cell_angle_alpha                79.263(3)
_cell_angle_beta                 68.067(4)
_cell_angle_gamma                83.306(4)
_cell_volume                     1262.84(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    7586
_cell_measurement_theta_min      3.6280
_cell_measurement_theta_max      28.3240

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_F_000             670
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.153
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.90030
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_reflns_number            12243
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.465
_diffrn_reflns_theta_max         28.569
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5461
_reflns_number_gt                4874
_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 1.171.41.120a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0271P)²+1.0161P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     .
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5461
_refine_ls_number_parameters     357
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0731
_refine_ls_wR_factor_gt          0.0699
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.57887(3) 0.77333(2) 0.24376(2) 0.00960(7) Uani 1 1 d . . . . .
O1 O 0.29319(15) 0.72488(11) 0.23552(12) 0.0140(3) Uani 1 1 d . . . . .
N2 N 0.44550(18) 0.68756(13) 0.20521(15) 0.0124(3) Uani 1 1 d . . . . .
C3 C 0.4568(2) 0.58562(15) 0.17370(16) 0.0114(4) Uani 1 1 d . . . . .
C4 C 0.3166(2) 0.55483(16) 0.18003(17) 0.0139(4) Uani 1 1 d . . . . .
H4 H 0.294586 0.486871 0.161363 0.017 Uiso 1 1 calc R U . . .
C5 C 0.2208(2) 0.64315(16) 0.21843(18) 0.0143(4) Uani 1 1 d . . . . .
C51 C 0.0585(2) 0.66683(19) 0.2438(2) 0.0221(5) Uani 1 1 d . . . . .
H51A H 0.043968 0.723456 0.178351 0.033 Uiso 1 1 calc R U . . .
H51B H 0.011768 0.696226 0.320955 0.033 Uiso 1 1 calc R U . . .
H51C H 0.012232 0.596503 0.248878 0.033 Uiso 1 1 calc R U . . .
N6 N 0.58714(19) 0.52134(13) 0.14025(15) 0.0136(3) Uani 1 1 d . . . . .
H6 H 0.583163 0.457029 0.126030 0.016 Uiso 1 1 d R U . . .
C7 C 0.7226(2) 0.54552(16) 0.15409(17) 0.0128(4) Uani 1 1 d . . . . .
H7 H 0.804006 0.489111 0.116630 0.015 Uiso 1 1 calc R U . . .
O7 O 0.76888(16) 0.65607(11) 0.09625(12) 0.0145(3) Uani 1 1 d . . . . .
C71 C 0.8055(3) 0.6726(2) -0.03305(19) 0.0256(5) Uani 1 1 d . . . . .
H71A H 0.871221 0.608726 -0.066713 0.038 Uiso 1 1 calc R U . . .
H71B H 0.856944 0.743595 -0.069973 0.038 Uiso 1 1 calc R U . . .
H71C H 0.713264 0.676552 -0.050485 0.038 Uiso 1 1 calc R U . . .
C8 C 0.7070(2) 0.53973(16) 0.28500(17) 0.0115(4) Uani 1 1 d . . . . .
N9 N 0.64009(18) 0.63181(13) 0.33705(14) 0.0104(3) Uani 1 1 d . . . . .
C10 C 0.6248(2) 0.63357(16) 0.45217(17) 0.0113(4) Uani 1 1 d . . . . .
C11 C 0.6776(2) 0.54410(16) 0.51875(18) 0.0143(4) Uani 1 1 d . . . . .
H11 H 0.668188 0.547850 0.599498 0.017 Uiso 1 1 calc R U . . .
C12 C 0.7446(2) 0.44871(17) 0.46577(19) 0.0165(4) Uani 1 1 d . . . . .
H12 H 0.780828 0.385805 0.510153 0.020 Uiso 1 1 calc R U . . .
C13 C 0.7583(2) 0.44602(16) 0.34744(19) 0.0147(4) Uani 1 1 d . . . . .
H13 H 0.802091 0.380852 0.310026 0.018 Uiso 1 1 calc R U . . .
C14 C 0.5508(2) 0.74043(16) 0.50491(17) 0.0118(4) Uani 1 1 d . . . . .
H14 H 0.497273 0.719634 0.594320 0.014 Uiso 1 1 calc R U . . .
O14 O 0.44420(15) 0.78176(11) 0.44995(12) 0.0118(3) Uani 1 1 d . . . . .
C141 C 0.3508(2) 0.87722(17) 0.4987(2) 0.0190(4) Uani 1 1 d . . . . .
H14A H 0.306390 0.858617 0.587223 0.028 Uiso 1 1 calc R U . . .
H14B H 0.270814 0.894335 0.465194 0.028 Uiso 1 1 calc R U . . .
H14C H 0.411562 0.943630 0.476656 0.028 Uiso 1 1 calc R U . . .
N15 N 0.65896(18) 0.82362(13) 0.48384(14) 0.0121(3) Uani 1 1 d . . . . .
H15 H 0.667544 0.845397 0.546843 0.015 Uiso 1 1 calc R U . . .
C16 C 0.7477(2) 0.86944(15) 0.37088(17) 0.0103(4) Uani 1 1 d . . . . .
N17 N 0.72616(18) 0.85379(13) 0.27279(14) 0.0111(3) Uani 1 1 d . . . . .
O18 O 0.83454(15) 0.91504(11) 0.17278(12) 0.0120(3) Uani 1 1 d . . . . .
C19 C 0.9161(2) 0.96659(15) 0.21769(18) 0.0119(4) Uani 1 1 d . . . . .
C191 C 1.0363(2) 1.03697(17) 0.12655(18) 0.0154(4) Uani 1 1 d . . . . .
H19A H 0.992498 1.097386 0.080649 0.023 Uiso 1 1 calc R U . . .
H19B H 1.108368 0.989194 0.070891 0.023 Uiso 1 1 calc R U . . .
H19C H 1.087659 1.070958 0.167704 0.023 Uiso 1 1 calc R U . . .
C20 C 0.8687(2) 0.94072(15) 0.33913(18) 0.0119(4) Uani 1 1 d . . . . .
H20 H 0.907707 0.964844 0.392094 0.014 Uiso 1 1 calc R U . . .
O1A O 0.52343(17) 0.92403(11) 0.16592(13) 0.0181(3) Uani 1 1 d . . . . .
H1A H 0.555181 0.977045 0.183482 0.022 Uiso 1 1 d R U . . .
C1A C 0.3833(3) 0.96639(18) 0.1509(2) 0.0209(5) Uani 1 1 d . . . . .
H1AA H 0.362432 0.921870 0.098879 0.031 Uiso 1 1 calc R U . . .
H1AB H 0.390779 1.046462 0.113342 0.031 Uiso 1 1 calc R U . . .
H1AC H 0.301992 0.959494 0.230428 0.031 Uiso 1 1 calc R U . . .
Cl1B Cl 0.92669(5) 0.77048(4) 0.62467(4) 0.01498(11) Uani 1 1 d . . . . .
O1B O 0.8488(2) 0.66823(16) 0.66812(19) 0.0485(6) Uani 1 1 d . . . . .
O2B O 1.02224(19) 0.77116(14) 0.50032(14) 0.0293(4) Uani 1 1 d . . . . .
O3B O 0.82058(19) 0.86694(14) 0.63283(15) 0.0292(4) Uani 1 1 d . . . . .
O4B O 1.01406(18) 0.77818(13) 0.69620(14) 0.0247(4) Uani 1 1 d . . . . .
Cl1C Cl 0.64150(6) 0.21308(4) 0.13735(4) 0.01515(11) Uani 1 1 d . . . . .
O1C O 0.73418(19) 0.27226(13) 0.17393(16) 0.0282(4) Uani 1 1 d . . . . .
O2C O 0.7286(2) 0.16869(14) 0.02853(15) 0.0337(4) Uani 1 1 d . . . . .
O3C O 0.57632(19) 0.11998(12) 0.23271(14) 0.0254(4) Uani 1 1 d . . . . .
O4C O 0.52432(19) 0.29107(13) 0.11785(17) 0.0311(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.9622(17) . ?
Cu1 N17 1.9689(16) . ?
Cu1 O1A 1.9852(14) . ?
Cu1 N9 2.0084(16) . ?
Cu1 O14 2.3452(13) . ?
Cu1 O7 2.5245(14) . ?
O1 C5 1.352(2) . ?
O1 N2 1.411(2) . ?
N2 C3 1.326(2) . ?
C3 N6 1.357(3) . ?
C3 C4 1.412(3) . ?
C4 C5 1.349(3) . ?
C4 H4 0.9500 . ?
C5 C51 1.479(3) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
N6 C7 1.443(3) . ?
N6 H6 0.8279 . ?
C7 O7 1.414(2) . ?
C7 C8 1.513(3) . ?
C7 H7 1.0000 . ?
O7 C71 1.440(2) . ?
C71 H71A 0.9800 . ?
C71 H71B 0.9800 . ?
C71 H71C 0.9800 . ?
C8 N9 1.347(2) . ?
C8 C13 1.379(3) . ?
N9 C10 1.340(2) . ?
C10 C11 1.381(3) . ?
C10 C14 1.517(3) . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O14 1.415(2) . ?
C14 N15 1.447(2) . ?
C14 H14 1.0000 . ?
O14 C141 1.441(2) . ?
C141 H14A 0.9800 . ?
C141 H14B 0.9800 . ?
C141 H14C 0.9800 . ?
N15 C16 1.357(2) . ?
N15 H15 0.8800 . ?
C16 N17 1.320(2) . ?
C16 C20 1.419(3) . ?
N17 O18 1.4093(19) . ?
O18 C19 1.358(2) . ?
C19 C20 1.343(3) . ?
C19 C191 1.479(3) . ?
C191 H19A 0.9800 . ?
C191 H19B 0.9800 . ?
C191 H19C 0.9800 . ?
C20 H20 0.9500 . ?
O1A C1A 1.448(2) . ?
O1A H1A 0.8277 . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
Cl1B O1B 1.4212(18) . ?
Cl1B O4B 1.4297(16) . ?
Cl1B O2B 1.4324(16) . ?
Cl1B O3B 1.4428(15) . ?
Cl1C O2C 1.4263(16) . ?
Cl1C O1C 1.4317(16) . ?
Cl1C O4C 1.4393(16) . ?
Cl1C O3C 1.4500(15) . ?

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
N2 Cu1 N17 175.45(7) . . ?
N2 Cu1 O1A 95.57(6) . . ?
N17 Cu1 O1A 85.89(6) . . ?
N2 Cu1 N9 90.86(7) . . ?
N17 Cu1 N9 87.96(7) . . ?
O1A Cu1 N9 172.63(6) . . ?
N2 Cu1 O14 101.23(6) . . ?
N17 Cu1 O14 82.65(6) . . ?
O1A Cu1 O14 101.77(5) . . ?
N9 Cu1 O14 73.35(5) . . ?
N2 Cu1 O7 79.49(6) . . ?
N17 Cu1 O7 95.97(6) . . ?
O1A Cu1 O7 113.76(5) . . ?
N9 Cu1 O7 70.94(5) . . ?
O14 Cu1 O7 144.29(5) . . ?
C5 O1 N2 107.52(14) . . ?
C3 N2 O1 106.20(15) . . ?
C3 N2 Cu1 133.83(14) . . ?
O1 N2 Cu1 118.80(11) . . ?
N2 C3 N6 123.52(18) . . ?
N2 C3 C4 110.81(17) . . ?
N6 C3 C4 125.68(17) . . ?
C5 C4 C3 104.83(17) . . ?
C5 C4 H4 127.6 . . ?
C3 C4 H4 127.6 . . ?
C4 C5 O1 110.63(18) . . ?
C4 C5 C51 133.33(19) . . ?
O1 C5 C51 116.04(17) . . ?
C5 C51 H51A 109.5 . . ?
C5 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C5 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C3 N6 C7 124.46(16) . . ?
C3 N6 H6 117.2 . . ?
C7 N6 H6 116.8 . . ?
O7 C7 N6 111.80(16) . . ?
O7 C7 C8 105.79(15) . . ?
N6 C7 C8 113.49(16) . . ?
O7 C7 H7 108.5 . . ?
N6 C7 H7 108.5 . . ?
C8 C7 H7 108.5 . . ?
C7 O7 C71 113.30(15) . . ?
C7 O7 Cu1 100.16(10) . . ?
C71 O7 Cu1 126.37(13) . . ?
O7 C71 H71A 109.5 . . ?
O7 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
O7 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
N9 C8 C13 121.88(18) . . ?
N9 C8 C7 115.97(16) . . ?
C13 C8 C7 122.14(17) . . ?
C10 N9 C8 119.29(16) . . ?
C10 N9 Cu1 118.18(12) . . ?
C8 N9 Cu1 122.28(13) . . ?
N9 C10 C11 121.84(17) . . ?
N9 C10 C14 116.76(16) . . ?
C11 C10 C14 121.38(17) . . ?
C10 C11 C12 118.87(18) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C13 C12 C11 119.34(18) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C8 C13 C12 118.74(18) . . ?
C8 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
O14 C14 N15 112.18(15) . . ?
O14 C14 C10 105.83(15) . . ?
N15 C14 C10 111.89(16) . . ?
O14 C14 H14 108.9 . . ?
N15 C14 H14 108.9 . . ?
C10 C14 H14 108.9 . . ?
C14 O14 C141 113.86(15) . . ?
C14 O14 Cu1 103.21(10) . . ?
C141 O14 Cu1 125.72(12) . . ?
O14 C141 H14A 109.5 . . ?
O14 C141 H14B 109.5 . . ?
H14A C141 H14B 109.5 . . ?
O14 C141 H14C 109.5 . . ?
H14A C141 H14C 109.5 . . ?
H14B C141 H14C 109.5 . . ?
C16 N15 C14 122.67(16) . . ?
C16 N15 H15 118.7 . . ?
C14 N15 H15 118.7 . . ?
N17 C16 N15 121.87(17) . . ?
N17 C16 C20 110.50(17) . . ?
N15 C16 C20 127.61(18) . . ?
C16 N17 O18 106.81(15) . . ?
C16 N17 Cu1 134.33(13) . . ?
O18 N17 Cu1 118.81(11) . . ?
C19 O18 N17 106.99(14) . . ?
C20 C19 O18 110.91(17) . . ?
C20 C19 C191 133.44(19) . . ?
O18 C19 C191 115.65(17) . . ?
C19 C191 H19A 109.5 . . ?
C19 C191 H19B 109.5 . . ?
H19A C191 H19B 109.5 . . ?
C19 C191 H19C 109.5 . . ?
H19A C191 H19C 109.5 . . ?
H19B C191 H19C 109.5 . . ?
C19 C20 C16 104.78(17) . . ?
C19 C20 H20 127.6 . . ?
C16 C20 H20 127.6 . . ?
C1A O1A Cu1 130.00(12) . . ?
C1A O1A H1A 106.4 . . ?
Cu1 O1A H1A 112.3 . . ?
O1A C1A H1AA 109.5 . . ?
O1A C1A H1AB 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
O1A C1A H1AC 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
O1B Cl1B O4B 109.76(12) . . ?
O1B Cl1B O2B 109.30(12) . . ?
O4B Cl1B O2B 109.97(10) . . ?
O1B Cl1B O3B 109.69(12) . . ?
O4B Cl1B O3B 109.15(9) . . ?
O2B Cl1B O3B 108.97(10) . . ?
O2C Cl1C O1C 110.21(11) . . ?
O2C Cl1C O4C 109.99(11) . . ?
O1C Cl1C O4C 108.72(10) . . ?
O2C Cl1C O3C 109.17(10) . . ?
O1C Cl1C O3C 108.99(10) . . ?
O4C Cl1C O3C 109.74(10) . . ?

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
C5 O1 N2 C3 -1.02(19) . . . . ?
C5 O1 N2 Cu1 -170.29(12) . . . . ?
O1 N2 C3 N6 -178.91(16) . . . . ?
Cu1 N2 C3 N6 -12.0(3) . . . . ?
O1 N2 C3 C4 1.1(2) . . . . ?
Cu1 N2 C3 C4 168.02(14) . . . . ?
N2 C3 C4 C5 -0.7(2) . . . . ?
N6 C3 C4 C5 179.25(18) . . . . ?
C3 C4 C5 O1 0.1(2) . . . . ?
C3 C4 C5 C51 179.8(2) . . . . ?
N2 O1 C5 C4 0.6(2) . . . . ?
N2 O1 C5 C51 -179.17(17) . . . . ?
N2 C3 N6 C7 11.1(3) . . . . ?
C4 C3 N6 C7 -168.93(18) . . . . ?
C3 N6 C7 O7 -55.9(2) . . . . ?
C3 N6 C7 C8 63.7(2) . . . . ?
N6 C7 O7 C71 -62.5(2) . . . . ?
C8 C7 O7 C71 173.50(17) . . . . ?
N6 C7 O7 Cu1 74.65(15) . . . . ?
C8 C7 O7 Cu1 -49.35(15) . . . . ?
O7 C7 C8 N9 42.9(2) . . . . ?
N6 C7 C8 N9 -80.0(2) . . . . ?
O7 C7 C8 C13 -137.02(18) . . . . ?
N6 C7 C8 C13 100.0(2) . . . . ?
C13 C8 N9 C10 1.1(3) . . . . ?
C7 C8 N9 C10 -178.79(17) . . . . ?
C13 C8 N9 Cu1 175.31(14) . . . . ?
C7 C8 N9 Cu1 -4.6(2) . . . . ?
C8 N9 C10 C11 0.9(3) . . . . ?
Cu1 N9 C10 C11 -173.55(15) . . . . ?
C8 N9 C10 C14 179.02(16) . . . . ?
Cu1 N9 C10 C14 4.6(2) . . . . ?
N9 C10 C11 C12 -1.8(3) . . . . ?
C14 C10 C11 C12 -179.81(18) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
N9 C8 C13 C12 -2.2(3) . . . . ?
C7 C8 C13 C12 177.75(18) . . . . ?
C11 C12 C13 C8 1.2(3) . . . . ?
N9 C10 C14 O14 33.0(2) . . . . ?
C11 C10 C14 O14 -148.86(18) . . . . ?
N9 C10 C14 N15 -89.5(2) . . . . ?
C11 C10 C14 N15 88.7(2) . . . . ?
N15 C14 O14 C141 -63.9(2) . . . . ?
C10 C14 O14 C141 173.78(15) . . . . ?
N15 C14 O14 Cu1 75.49(15) . . . . ?
C10 C14 O14 Cu1 -46.79(14) . . . . ?
O14 C14 N15 C16 -58.4(2) . . . . ?
C10 C14 N15 C16 60.4(2) . . . . ?
C14 N15 C16 N17 10.1(3) . . . . ?
C14 N15 C16 C20 -171.93(18) . . . . ?
N15 C16 N17 O18 178.47(16) . . . . ?
C20 C16 N17 O18 0.2(2) . . . . ?
N15 C16 N17 Cu1 1.3(3) . . . . ?
C20 C16 N17 Cu1 -176.98(13) . . . . ?
C16 N17 O18 C19 -0.76(19) . . . . ?
Cu1 N17 O18 C19 176.93(11) . . . . ?
N17 O18 C19 C20 1.1(2) . . . . ?
N17 O18 C19 C191 -179.40(15) . . . . ?
O18 C19 C20 C16 -0.9(2) . . . . ?
C191 C19 C20 C16 179.7(2) . . . . ?
N17 C16 C20 C19 0.4(2) . . . . ?
N15 C16 C20 C19 -177.71(18) . . . . ?

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
C51 H51B O2B 0.98 2.52 3.425(3) 152.7 1_455 yes
N6 H6 O4C 0.83 2.16 2.973(2) 167.6 . yes
C13 H13 O4B 0.95 2.44 3.255(2) 144.1 2_766 yes
N15 H15 O3B 0.88 2.15 2.919(2) 145.2 . yes
C191 H19B O2C 0.98 2.49 3.455(3) 166.4 2_765 yes
C1A H1AA O2C 0.98 2.48 3.447(3) 170.3 2_665 yes

_refine_diff_density_max         0.409
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.068



####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1965452'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2019-11-13 deposited with the CCDC.	2022-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C19 H27 Cu N5 O5, 2(C F3 O3 S), C2 H6 O
;
_chemical_formula_sum            'C23 H33 Cu F6 N5 O12 S2'
_chemical_formula_weight         813.20

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'
F F 0.0171 0.0103 '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                   9.5535(7)
_cell_length_b                   9.9440(6)
_cell_length_c                   17.7730(11)
_cell_angle_alpha                92.720(5)
_cell_angle_beta                 90.720(5)
_cell_angle_gamma                94.166(5)
_cell_volume                     1681.86(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    5533
_cell_measurement_theta_min      3.6900
_cell_measurement_theta_max      26.9190

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_F_000             834
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.871
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.74717
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.2413
_diffrn_reflns_number            12543
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.073
_diffrn_reflns_theta_max         26.984
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6737
_reflns_number_gt                6071
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'

_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)+(0.0344P)²+1.2925P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     .
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6737
_refine_ls_number_parameters     456
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0829
_refine_ls_wR_factor_gt          0.0797
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.043
_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
Cu01 Cu 0.76778(2) 0.49263(2) 0.73520(2) 0.01332(7) Uani 1 1 d . . . . .
O1 O 1.06620(14) 0.48342(15) 0.77639(8) 0.0190(3) Uani 1 1 d . . . . .
N2 N 0.92847(17) 0.47522(18) 0.80502(10) 0.0172(4) Uani 1 1 d . . . . .
C3 C 0.9381(2) 0.4293(2) 0.87345(12) 0.0178(4) Uani 1 1 d . . . . .
C4 C 1.0796(2) 0.4069(2) 0.89181(12) 0.0216(5) Uani 1 1 d . . . . .
H4 H 1.1148 0.3742 0.9372 0.026 Uiso 1 1 calc R U . . .
C5 C 1.1524(2) 0.4423(2) 0.83063(12) 0.0212(4) Uani 1 1 d . . . . .
C51 C 1.3036(2) 0.4466(3) 0.81185(15) 0.0344(6) Uani 1 1 d . . . . .
H51A H 1.3156 0.3926 0.7651 0.052 Uiso 1 1 calc R U . . .
H51B H 1.3561 0.4096 0.8528 0.052 Uiso 1 1 calc R U . . .
H51C H 1.3389 0.5402 0.8052 0.052 Uiso 1 1 calc R U . . .
N6 N 0.82676(18) 0.41286(19) 0.91948(10) 0.0212(4) Uani 1 1 d . . . . .
H6 H 0.8433 0.3981 0.9671 0.025 Uiso 1 1 calc R U . . .
C7 C 0.6817(2) 0.4181(2) 0.89481(12) 0.0198(4) Uani 1 1 d . . . . .
H7 H 0.6199 0.4140 0.9398 0.024 Uiso 1 1 calc R U . . .
O7 O 0.65983(15) 0.53705(14) 0.85718(8) 0.0186(3) Uani 1 1 d . . . . .
C71 C 0.6846(3) 0.6618(2) 0.90265(13) 0.0273(5) Uani 1 1 d . . . . .
H71A H 0.7852 0.6770 0.9168 0.033 Uiso 1 1 calc R U . . .
H71B H 0.6293 0.6576 0.9493 0.033 Uiso 1 1 calc R U . . .
C72 C 0.6401(3) 0.7742(2) 0.85592(13) 0.0284(5) Uani 1 1 d . . . . .
H72A H 0.6952 0.7769 0.8098 0.043 Uiso 1 1 calc R U . . .
H72B H 0.6561 0.8604 0.8848 0.043 Uiso 1 1 calc R U . . .
H72C H 0.5402 0.7583 0.8427 0.043 Uiso 1 1 calc R U . . .
C8 C 0.6352(2) 0.3023(2) 0.83920(12) 0.0180(4) Uani 1 1 d . . . . .
N9 N 0.67392(16) 0.31749(17) 0.76740(9) 0.0152(3) Uani 1 1 d . . . . .
C10 C 0.6363(2) 0.2209(2) 0.71424(12) 0.0165(4) Uani 1 1 d . . . . .
C11 C 0.5560(2) 0.1042(2) 0.73118(13) 0.0227(5) Uani 1 1 d . . . . .
H11 H 0.5299 0.0366 0.6930 0.027 Uiso 1 1 calc R U . . .
C12 C 0.5149(2) 0.0886(2) 0.80508(13) 0.0246(5) Uani 1 1 d . . . . .
H12 H 0.4588 0.0104 0.8180 0.030 Uiso 1 1 calc R U . . .
C13 C 0.5561(2) 0.1879(2) 0.85992(13) 0.0225(5) Uani 1 1 d . . . . .
H13 H 0.5305 0.1777 0.9109 0.027 Uiso 1 1 calc R U . . .
C14 C 0.6814(2) 0.2468(2) 0.63417(12) 0.0168(4) Uani 1 1 d . . . . .
H14 H 0.6954 0.1585 0.6071 0.020 Uiso 1 1 calc R U . . .
O14 O 0.81268(14) 0.32376(14) 0.64112(8) 0.0161(3) Uani 1 1 d . . . . .
C141 C 0.8794(2) 0.3446(2) 0.56961(12) 0.0215(5) Uani 1 1 d . . . . .
H14A H 0.8258 0.4054 0.5396 0.026 Uiso 1 1 calc R U . . .
H14B H 0.8829 0.2574 0.5406 0.026 Uiso 1 1 calc R U . . .
C142 C 1.0258(2) 0.4068(2) 0.58564(12) 0.0233(5) Uani 1 1 d . . . . .
H14C H 1.0767 0.4141 0.5383 0.035 Uiso 1 1 calc R U . . .
H14D H 1.0750 0.3499 0.6192 0.035 Uiso 1 1 calc R U . . .
H14E H 1.0210 0.4970 0.6099 0.035 Uiso 1 1 calc R U . . .
N15 N 0.57764(17) 0.31521(17) 0.59337(10) 0.0176(4) Uani 1 1 d . . . . .
H15 H 0.5439 0.2779 0.5504 0.021 Uiso 1 1 calc R U . . .
C16 C 0.5301(2) 0.4348(2) 0.61861(11) 0.0150(4) Uani 1 1 d . . . . .
N17 N 0.59563(17) 0.51068(16) 0.67322(9) 0.0151(3) Uani 1 1 d . . . . .
O18 O 0.51576(14) 0.62374(14) 0.68624(8) 0.0161(3) Uani 1 1 d . . . . .
C19 C 0.4047(2) 0.6097(2) 0.63706(11) 0.0172(4) Uani 1 1 d . . . . .
C191 C 0.3048(2) 0.7170(2) 0.64489(13) 0.0235(5) Uani 1 1 d . . . . .
H19A H 0.2682 0.7199 0.6962 0.035 Uiso 1 1 calc R U . . .
H19B H 0.2268 0.6975 0.6087 0.035 Uiso 1 1 calc R U . . .
H19C H 0.3533 0.8044 0.6349 0.035 Uiso 1 1 calc R U . . .
C20 C 0.4088(2) 0.4955(2) 0.59327(11) 0.0175(4) Uani 1 1 d . . . . .
H20 H 0.3448 0.4628 0.5541 0.021 Uiso 1 1 calc R U . . .
O1W O 0.86133(15) 0.64848(14) 0.69048(8) 0.0200(3) Uani 1 1 d . . . . .
H1W1 H 0.8996 0.7156 0.7152 0.030 Uiso 1 1 d R U . . .
H1W2 H 0.8251 0.6746 0.6521 0.030 Uiso 1 1 d R U . . .
C1A C 0.2244(2) 0.0942(2) 0.53178(13) 0.0216(5) Uani 1 1 d . . . . .
F1A F 0.24567(16) -0.03589(13) 0.53711(9) 0.0367(4) Uani 1 1 d . . . . .
F2A F 0.08661(13) 0.10584(14) 0.52999(8) 0.0318(3) Uani 1 1 d . . . . .
F3A F 0.27579(14) 0.16109(14) 0.59449(7) 0.0299(3) Uani 1 1 d . . . . .
S1A S 0.30803(5) 0.16173(5) 0.44833(3) 0.01730(11) Uani 1 1 d . . . . .
O1A O 0.45565(15) 0.15897(16) 0.46610(8) 0.0237(3) Uani 1 1 d . . . . .
O2A O 0.25576(18) 0.07014(16) 0.38756(9) 0.0293(4) Uani 1 1 d . . . . .
O3A O 0.25888(16) 0.29657(14) 0.44642(8) 0.0215(3) Uani 1 1 d . . . . .
C1B C 1.2213(3) 0.9575(3) 0.97199(13) 0.0306(5) Uani 1 1 d . . . . .
F1B F 1.1253(2) 1.03231(16) 0.94381(9) 0.0519(4) Uani 1 1 d . . . . .
F2B F 1.34597(19) 1.0265(2) 0.96838(10) 0.0612(5) Uani 1 1 d . . . . .
F3B F 1.19419(16) 0.94439(16) 1.04484(8) 0.0382(4) Uani 1 1 d . . . . .
S1B S 1.22172(6) 0.79365(6) 0.92253(3) 0.02402(13) Uani 1 1 d . . . . .
O1B O 1.33865(19) 0.7335(2) 0.95593(10) 0.0424(5) Uani 1 1 d . . . . .
O2B O 1.08678(18) 0.72962(17) 0.94049(10) 0.0336(4) Uani 1 1 d . . . . .
O3B O 1.23996(17) 0.82660(17) 0.84452(8) 0.0291(4) Uani 1 1 d . . . . .
O1C O 1.0005(2) 0.85171(18) 0.75758(13) 0.0543(6) Uani 1 1 d . U . . .
H1C H 1.0685 0.8435 0.7870 0.081 Uiso 1 1 d R U . A .
C1C C 0.9442(4) 0.9840(4) 0.77159(19) 0.0297(10) Uani 0.693(7) 1 d . U P A 1
H1C1 H 0.8500 0.9825 0.7476 0.036 Uiso 0.693(7) 1 calc R U P A 1
H1C2 H 0.9331 1.0000 0.8265 0.036 Uiso 0.693(7) 1 calc R U P A 1
C1C' C 1.0375(9) 0.9751(9) 0.7204(5) 0.037(2) Uani 0.307(7) 1 d . U P A 2
H1C3 H 1.1372 0.9702 0.7065 0.044 Uiso 0.307(7) 1 calc R U P A 2
H1C4 H 0.9833 0.9672 0.6724 0.044 Uiso 0.307(7) 1 calc R U P A 2
C2C C 1.0281(5) 1.0899(4) 0.7446(3) 0.0904(14) Uani 1 1 d . U . . .
H2C1 H 1.0419 1.0745 0.6916 0.136 Uiso 0.693(7) 1 d R U P A 1
H2C2 H 1.1173 1.0972 0.7705 0.136 Uiso 0.693(7) 1 d R U P A 1
H2C3 H 0.9825 1.1720 0.7533 0.136 Uiso 0.693(7) 1 d R U P A 1
H2C4 H 0.9558 1.0888 0.7817 0.136 Uiso 0.307(7) 1 d R U P A 2
H2C5 H 1.0035 1.1456 0.7045 0.136 Uiso 0.307(7) 1 d R U P A 2
H2C6 H 1.1154 1.1255 0.7675 0.136 Uiso 0.307(7) 1 d R U P A 2


_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
Cu01 O1W 1.9405(14) . ?
Cu01 N2 1.9844(16) . ?
Cu01 N17 1.9917(16) . ?
Cu01 N9 2.0113(17) . ?
Cu01 O14 2.3783(14) . ?
O1 C5 1.357(2) . ?
O1 N2 1.415(2) . ?
N2 C3 1.324(3) . ?
C3 N6 1.355(3) . ?
C3 C4 1.422(3) . ?
C4 C5 1.345(3) . ?
C4 H4 0.9500 . ?
C5 C51 1.485(3) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
N6 C7 1.454(3) . ?
N6 H6 0.8800 . ?
C7 O7 1.413(2) . ?
C7 C8 1.519(3) . ?
C7 H7 1.0000 . ?
O7 C71 1.451(3) . ?
C71 C72 1.506(3) . ?
C71 H71A 0.9900 . ?
C71 H71B 0.9900 . ?
C72 H72A 0.9800 . ?
C72 H72B 0.9800 . ?
C72 H72C 0.9800 . ?
C8 N9 1.345(3) . ?
C8 C13 1.387(3) . ?
N9 C10 1.341(3) . ?
C10 C11 1.392(3) . ?
C10 C14 1.520(3) . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O14 1.422(2) . ?
C14 N15 1.448(2) . ?
C14 H14 1.0000 . ?
O14 C141 1.446(2) . ?
C141 C142 1.506(3) . ?
C141 H14A 0.9900 . ?
C141 H14B 0.9900 . ?
C142 H14C 0.9800 . ?
C142 H14D 0.9800 . ?
C142 H14E 0.9800 . ?
N15 C16 1.362(3) . ?
N15 H15 0.8800 . ?
C16 N17 1.323(3) . ?
C16 C20 1.423(3) . ?
N17 O18 1.416(2) . ?
O18 C19 1.361(2) . ?
C19 C20 1.349(3) . ?
C19 C191 1.486(3) . ?
C191 H19A 0.9800 . ?
C191 H19B 0.9800 . ?
C191 H19C 0.9800 . ?
C20 H20 0.9500 . ?
O1W H1W1 0.8395 . ?
O1W H1W2 0.8232 . ?
C1A F2A 1.330(2) . ?
C1A F1A 1.332(2) . ?
C1A F3A 1.339(3) . ?
C1A S1A 1.826(2) . ?
S1A O2A 1.4396(15) . ?
S1A O1A 1.4439(15) . ?
S1A O3A 1.4543(15) . ?
C1B F1B 1.329(3) . ?
C1B F3B 1.334(3) . ?
C1B F2B 1.335(3) . ?
C1B S1B 1.815(3) . ?
S1B O1B 1.4397(18) . ?
S1B O2B 1.4421(17) . ?
S1B O3B 1.4494(16) . ?
O1C C1C' 1.445(8) . ?
O1C C1C 1.469(4) . ?
O1C H1C 0.8401 . ?
C1C C2C 1.383(5) . ?
C1C H1C1 0.9900 . ?
C1C H1C2 0.9900 . ?
C1C' C2C 1.210(10) . ?
C1C' H1C3 0.9900 . ?
C1C' H1C4 0.9900 . ?
C2C H2C1 0.9601 . ?
C2C H2C2 0.9600 . ?
C2C H2C3 0.9600 . ?
C2C H2C4 0.9600 . ?
C2C H2C5 0.9599 . ?
C2C H2C6 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1W Cu01 N2 92.09(6) . . ?
O1W Cu01 N17 90.88(6) . . ?
N2 Cu01 N17 174.86(7) . . ?
O1W Cu01 N9 171.94(7) . . ?
N2 Cu01 N9 91.03(7) . . ?
N17 Cu01 N9 86.58(7) . . ?
O1W Cu01 O14 99.31(6) . . ?
N2 Cu01 O14 100.03(6) . . ?
N17 Cu01 O14 83.61(6) . . ?
N9 Cu01 O14 72.81(6) . . ?
C5 O1 N2 107.24(15) . . ?
C3 N2 O1 106.35(15) . . ?
C3 N2 Cu01 133.06(14) . . ?
O1 N2 Cu01 119.02(12) . . ?
N2 C3 N6 123.13(18) . . ?
N2 C3 C4 110.80(19) . . ?
N6 C3 C4 126.01(19) . . ?
C5 C4 C3 104.58(18) . . ?
C5 C4 H4 127.7 . . ?
C3 C4 H4 127.7 . . ?
C4 C5 O1 111.03(18) . . ?
C4 C5 C51 133.5(2) . . ?
O1 C5 C51 115.52(19) . . ?
C5 C51 H51A 109.5 . . ?
C5 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C5 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C3 N6 C7 123.85(17) . . ?
C3 N6 H6 118.1 . . ?
C7 N6 H6 118.1 . . ?
O7 C7 N6 112.26(17) . . ?
O7 C7 C8 105.53(16) . . ?
N6 C7 C8 112.18(18) . . ?
O7 C7 H7 108.9 . . ?
N6 C7 H7 108.9 . . ?
C8 C7 H7 108.9 . . ?
C7 O7 C71 115.22(16) . . ?
O7 C71 C72 107.21(18) . . ?
O7 C71 H71A 110.3 . . ?
C72 C71 H71A 110.3 . . ?
O7 C71 H71B 110.3 . . ?
C72 C71 H71B 110.3 . . ?
H71A C71 H71B 108.5 . . ?
C71 C72 H72A 109.5 . . ?
C71 C72 H72B 109.5 . . ?
H72A C72 H72B 109.5 . . ?
C71 C72 H72C 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 109.5 . . ?
N9 C8 C13 121.3(2) . . ?
N9 C8 C7 115.92(18) . . ?
C13 C8 C7 122.81(19) . . ?
C10 N9 C8 120.08(17) . . ?
C10 N9 Cu01 118.47(13) . . ?
C8 N9 Cu01 121.04(14) . . ?
N9 C10 C11 121.54(19) . . ?
N9 C10 C14 116.96(17) . . ?
C11 C10 C14 121.47(19) . . ?
C12 C11 C10 118.6(2) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C8 C13 C12 119.0(2) . . ?
C8 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
O14 C14 N15 112.37(15) . . ?
O14 C14 C10 105.74(16) . . ?
N15 C14 C10 111.81(16) . . ?
O14 C14 H14 108.9 . . ?
N15 C14 H14 108.9 . . ?
C10 C14 H14 108.9 . . ?
C14 O14 C141 113.22(15) . . ?
C14 O14 Cu01 102.43(11) . . ?
C141 O14 Cu01 126.75(12) . . ?
O14 C141 C142 107.71(17) . . ?
O14 C141 H14A 110.2 . . ?
C142 C141 H14A 110.2 . . ?
O14 C141 H14B 110.2 . . ?
C142 C141 H14B 110.2 . . ?
H14A C141 H14B 108.5 . . ?
C141 C142 H14C 109.5 . . ?
C141 C142 H14D 109.5 . . ?
H14C C142 H14D 109.5 . . ?
C141 C142 H14E 109.5 . . ?
H14C C142 H14E 109.5 . . ?
H14D C142 H14E 109.5 . . ?
C16 N15 C14 122.84(17) . . ?
C16 N15 H15 118.6 . . ?
C14 N15 H15 118.6 . . ?
N17 C16 N15 121.84(17) . . ?
N17 C16 C20 110.69(18) . . ?
N15 C16 C20 127.46(18) . . ?
C16 N17 O18 106.55(15) . . ?
C16 N17 Cu01 133.74(14) . . ?
O18 N17 Cu01 119.70(11) . . ?
C19 O18 N17 107.26(14) . . ?
C20 C19 O18 110.66(18) . . ?
C20 C19 C191 134.39(19) . . ?
O18 C19 C191 114.89(18) . . ?
C19 C191 H19A 109.5 . . ?
C19 C191 H19B 109.5 . . ?
H19A C191 H19B 109.5 . . ?
C19 C191 H19C 109.5 . . ?
H19A C191 H19C 109.5 . . ?
H19B C191 H19C 109.5 . . ?
C19 C20 C16 104.82(18) . . ?
C19 C20 H20 127.6 . . ?
C16 C20 H20 127.6 . . ?
Cu01 O1W H1W1 124.4 . . ?
Cu01 O1W H1W2 116.9 . . ?
H1W1 O1W H1W2 108.6 . . ?
F2A C1A F1A 107.96(17) . . ?
F2A C1A F3A 107.37(18) . . ?
F1A C1A F3A 108.18(17) . . ?
F2A C1A S1A 111.36(15) . . ?
F1A C1A S1A 111.03(16) . . ?
F3A C1A S1A 110.79(14) . . ?
O2A S1A O1A 115.50(10) . . ?
O2A S1A O3A 114.61(9) . . ?
O1A S1A O3A 114.35(9) . . ?
O2A S1A C1A 104.11(10) . . ?
O1A S1A C1A 102.79(9) . . ?
O3A S1A C1A 103.22(10) . . ?
F1B C1B F3B 107.7(2) . . ?
F1B C1B F2B 107.8(2) . . ?
F3B C1B F2B 106.94(19) . . ?
F1B C1B S1B 111.96(17) . . ?
F3B C1B S1B 110.93(17) . . ?
F2B C1B S1B 111.25(18) . . ?
O1B S1B O2B 113.92(11) . . ?
O1B S1B O3B 114.76(10) . . ?
O2B S1B O3B 115.72(10) . . ?
O1B S1B C1B 103.82(12) . . ?
O2B S1B C1B 102.87(11) . . ?
O3B S1B C1B 103.51(11) . . ?
C1C' O1C H1C 104.4 . . ?
C1C O1C H1C 110.0 . . ?
C2C C1C O1C 113.5(3) . . ?
C2C C1C H1C1 108.9 . . ?
O1C C1C H1C1 108.9 . . ?
C2C C1C H1C2 108.9 . . ?
O1C C1C H1C2 108.9 . . ?
H1C1 C1C H1C2 107.7 . . ?
C2C C1C' O1C 127.7(8) . . ?
C2C C1C' H1C3 105.4 . . ?
O1C C1C' H1C3 105.4 . . ?
C2C C1C' H1C4 105.4 . . ?
O1C C1C' H1C4 105.4 . . ?
H1C3 C1C' H1C4 106.0 . . ?
C1C C2C H2C1 109.8 . . ?
C1C C2C H2C2 109.8 . . ?
H2C1 C2C H2C2 109.5 . . ?
C1C C2C H2C3 108.8 . . ?
H2C1 C2C H2C3 109.5 . . ?
H2C2 C2C H2C3 109.5 . . ?
C1C' C2C H2C4 108.1 . . ?
C1C' C2C H2C5 110.0 . . ?
H2C4 C2C H2C5 109.5 . . ?
C1C' C2C H2C6 110.3 . . ?
H2C4 C2C H2C6 109.5 . . ?
H2C5 C2C H2C6 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
C5 O1 N2 C3 -0.5(2) . . . . ?
C5 O1 N2 Cu01 -168.11(13) . . . . ?
O1 N2 C3 N6 177.60(19) . . . . ?
Cu01 N2 C3 N6 -17.3(3) . . . . ?
O1 N2 C3 C4 0.2(2) . . . . ?
Cu01 N2 C3 C4 165.32(16) . . . . ?
N2 C3 C4 C5 0.1(3) . . . . ?
N6 C3 C4 C5 -177.1(2) . . . . ?
C3 C4 C5 O1 -0.5(3) . . . . ?
C3 C4 C5 C51 178.7(3) . . . . ?
N2 O1 C5 C4 0.6(2) . . . . ?
N2 O1 C5 C51 -178.7(2) . . . . ?
N2 C3 N6 C7 12.3(3) . . . . ?
C4 C3 N6 C7 -170.7(2) . . . . ?
C3 N6 C7 O7 -52.7(3) . . . . ?
C3 N6 C7 C8 65.9(3) . . . . ?
N6 C7 O7 C71 -63.3(2) . . . . ?
C8 C7 O7 C71 174.25(17) . . . . ?
C7 O7 C71 C72 -173.60(18) . . . . ?
O7 C7 C8 N9 42.0(2) . . . . ?
N6 C7 C8 N9 -80.5(2) . . . . ?
O7 C7 C8 C13 -137.17(19) . . . . ?
N6 C7 C8 C13 100.3(2) . . . . ?
C13 C8 N9 C10 -0.1(3) . . . . ?
C7 C8 N9 C10 -179.31(17) . . . . ?
C13 C8 N9 Cu01 172.37(15) . . . . ?
C7 C8 N9 Cu01 -6.8(2) . . . . ?
C8 N9 C10 C11 0.6(3) . . . . ?
Cu01 N9 C10 C11 -172.05(15) . . . . ?
C8 N9 C10 C14 178.75(17) . . . . ?
Cu01 N9 C10 C14 6.1(2) . . . . ?
N9 C10 C11 C12 -0.1(3) . . . . ?
C14 C10 C11 C12 -178.14(18) . . . . ?
C10 C11 C12 C13 -0.9(3) . . . . ?
N9 C8 C13 C12 -0.9(3) . . . . ?
C7 C8 C13 C12 178.23(19) . . . . ?
C11 C12 C13 C8 1.4(3) . . . . ?
N9 C10 C14 O14 32.9(2) . . . . ?
C11 C10 C14 O14 -149.00(18) . . . . ?
N9 C10 C14 N15 -89.7(2) . . . . ?
C11 C10 C14 N15 88.4(2) . . . . ?
N15 C14 O14 C141 -64.5(2) . . . . ?
C10 C14 O14 C141 173.29(16) . . . . ?
N15 C14 O14 Cu01 75.10(16) . . . . ?
C10 C14 O14 Cu01 -47.14(15) . . . . ?
C14 O14 C141 C142 -170.99(17) . . . . ?
Cu01 O14 C141 C142 61.2(2) . . . . ?
O14 C14 N15 C16 -63.0(2) . . . . ?
C10 C14 N15 C16 55.7(2) . . . . ?
C14 N15 C16 N17 14.6(3) . . . . ?
C14 N15 C16 C20 -164.76(19) . . . . ?
N15 C16 N17 O18 -178.28(16) . . . . ?
C20 C16 N17 O18 1.2(2) . . . . ?
N15 C16 N17 Cu01 0.4(3) . . . . ?
C20 C16 N17 Cu01 179.81(14) . . . . ?
C16 N17 O18 C19 -0.54(19) . . . . ?
Cu01 N17 O18 C19 -179.41(12) . . . . ?
N17 O18 C19 C20 -0.3(2) . . . . ?
N17 O18 C19 C191 177.38(16) . . . . ?
O18 C19 C20 C16 1.0(2) . . . . ?
C191 C19 C20 C16 -176.1(2) . . . . ?
N17 C16 C20 C19 -1.4(2) . . . . ?
N15 C16 C20 C19 178.05(19) . . . . ?
F2A C1A S1A O2A -67.56(17) . . . . ?
F1A C1A S1A O2A 52.77(16) . . . . ?
F3A C1A S1A O2A 173.00(14) . . . . ?
F2A C1A S1A O1A 171.63(15) . . . . ?
F1A C1A S1A O1A -68.04(16) . . . . ?
F3A C1A S1A O1A 52.19(17) . . . . ?
F2A C1A S1A O3A 52.45(17) . . . . ?
F1A C1A S1A O3A 172.78(14) . . . . ?
F3A C1A S1A O3A -66.99(16) . . . . ?
F1B C1B S1B O1B 175.01(17) . . . . ?
F3B C1B S1B O1B -64.65(19) . . . . ?
F2B C1B S1B O1B 54.3(2) . . . . ?
F1B C1B S1B O2B -66.02(19) . . . . ?
F3B C1B S1B O2B 54.32(19) . . . . ?
F2B C1B S1B O2B 173.23(17) . . . . ?
F1B C1B S1B O3B 54.83(19) . . . . ?
F3B C1B S1B O3B 175.16(16) . . . . ?
F2B C1B S1B O3B -65.93(19) . . . . ?

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
N6 H6 O1B 0.88 2.55 3.095(3) 120.8 2_767
N6 H6 O2B 0.88 2.25 3.056(2) 152.6 2_767
C7 H7 O1B 1.00 2.46 3.114(3) 122.3 2_767
C13 H13 F2B 0.95 2.49 3.201(3) 131.2 1_445
C14 H14 O2A 1.00 2.36 3.257(3) 148.9 2_656
N15 H15 O1A 0.88 2.00 2.868(2) 167.6 .
O1W H1W1 O1C 0.84 1.74 2.572(2) 171.4 .
O1W H1W2 O3A 0.82 1.96 2.772(2) 169.7 2_666
O1C H1C O3B 0.84 1.94 2.778(2) 173.2 .

_refine_diff_density_max         0.672
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.063


