# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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 1943966'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2019-07-29 deposited with the CCDC.	2020-06-24 downloaded from the CCDC.
;
_audit_creation_date             2019-03-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C40 H34 Cl2 Cu N6 O6'
_chemical_formula_sum            'C40 H34 Cl2 Cu N6 O6'
_chemical_formula_weight         829.17
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

_cell_length_a                   7.5299(2)
_cell_length_b                   7.9870(2)
_cell_length_c                   14.8987(4)
_cell_angle_alpha                92.900(2)
_cell_angle_beta                 95.074(2)
_cell_angle_gamma                89.857(2)
_cell_volume                     891.37(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    26567
_cell_measurement_temperature    295
_cell_measurement_theta_max      71.61
_cell_measurement_theta_min      2.98
_shelx_estimated_absorpt_T_max   0.875
_shelx_estimated_absorpt_T_min   0.536
_exptl_absorpt_coefficient_mu    2.741
_exptl_absorpt_correction_T_max  0.647
_exptl_absorpt_correction_T_min  0.625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             427
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19646
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.200
_diffrn_reflns_theta_min         2.982
_diffrn_ambient_temperature      295
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari with Xenocs Genix3D Cu HF'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2802
_reflns_number_total             3341
_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       'X-Area Recipe 1.33.0.0 (STOE, 2015)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)'
_computing_data_reduction        
'X-Area Integrate 1.73.1.0 (STOE, 2018) X-Area LANA 1.73.2.0 (STOE, 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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0590P)²+0.3486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1125
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C1(H1), C2(H2), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C17(H17), C18(H18), C19(H19)
2.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.500000 1.000000 0.500000 0.03019(16) Uani 1 2 d S T P . .
Cl1 Cl -0.10625(13) 0.33622(10) 0.08533(7) 0.0719(3) Uani 1 1 d . . . . .
O1 O 0.3440(2) 0.9835(2) 0.38496(10) 0.0348(4) Uani 1 1 d . . . . .
O2 O 0.5728(2) 1.1432(2) 0.36335(11) 0.0389(4) Uani 1 1 d . . . . .
O3 O 1.1549(3) 0.4564(3) 0.36865(15) 0.0575(5) Uani 1 1 d . . . . .
N1 N 0.6467(3) 0.8081(2) 0.45584(13) 0.0331(4) Uani 1 1 d . . . . .
N2 N 0.9300(4) 0.2727(3) 0.33728(18) 0.0533(6) Uani 1 1 d . . . . .
H2A H 0.999643 0.194189 0.320172 0.064 Uiso 1 1 calc R . . . .
H2B H 0.817261 0.254603 0.336191 0.064 Uiso 1 1 calc R . . . .
N3 N 0.1082(3) 0.8972(3) 0.24725(14) 0.0408(5) Uani 1 1 d . . . . .
H3 H 0.125514 0.907921 0.305085 0.049 Uiso 1 1 calc R . . . .
C1 C 0.8222(4) 0.8282(3) 0.46000(18) 0.0410(6) Uani 1 1 d . . . . .
H1 H 0.870381 0.929600 0.484016 0.049 Uiso 1 1 calc R . . . .
C2 C 0.9363(4) 0.7070(3) 0.43069(18) 0.0403(6) Uani 1 1 d . . . . .
H2 H 1.058459 0.726908 0.434362 0.048 Uiso 1 1 calc R . . . .
C3 C 0.8667(3) 0.5544(3) 0.39554(16) 0.0358(5) Uani 1 1 d . . . . .
C4 C 0.6837(4) 0.5333(3) 0.39076(19) 0.0412(6) Uani 1 1 d . . . . .
H4 H 0.632006 0.432840 0.367553 0.049 Uiso 1 1 calc R . . . .
C5 C 0.5784(4) 0.6631(3) 0.42083(18) 0.0403(6) Uani 1 1 d . . . . .
H5 H 0.455360 0.648395 0.416429 0.048 Uiso 1 1 calc R . . . .
C6 C 0.9972(4) 0.4237(4) 0.36567(17) 0.0422(6) Uani 1 1 d . . . . .
C7 C 0.4325(3) 1.0697(3) 0.33331(15) 0.0299(5) Uani 1 1 d . . . . .
C8 C 0.3674(3) 1.0751(3) 0.23584(15) 0.0290(5) Uani 1 1 d . . . . .
C9 C 0.2165(3) 0.9850(3) 0.19626(15) 0.0298(5) Uani 1 1 d . . . . .
C10 C 0.1762(3) 0.9877(3) 0.10227(16) 0.0371(5) Uani 1 1 d . . . . .
H10 H 0.077782 0.928471 0.075212 0.045 Uiso 1 1 calc R . . . .
C11 C 0.2791(4) 1.0759(3) 0.05022(16) 0.0394(6) Uani 1 1 d . . . . .
H11 H 0.250748 1.074564 -0.011852 0.047 Uiso 1 1 calc R . . . .
C12 C 0.4257(4) 1.1678(3) 0.08864(17) 0.0399(6) Uani 1 1 d . . . . .
H12 H 0.494170 1.229469 0.053082 0.048 Uiso 1 1 calc R . . . .
C13 C 0.4671(3) 1.1656(3) 0.18010(17) 0.0352(5) Uani 1 1 d . . . . .
H13 H 0.565236 1.226634 0.205957 0.042 Uiso 1 1 calc R . . . .
C14 C -0.0324(3) 0.7886(3) 0.20773(15) 0.0335(5) Uani 1 1 d . . . . .
C15 C 0.0057(3) 0.6303(3) 0.16952(17) 0.0375(5) Uani 1 1 d . . . . .
C16 C -0.1411(4) 0.5356(3) 0.13340(18) 0.0401(6) Uani 1 1 d . . . . .
C17 C -0.3138(3) 0.5901(3) 0.13440(19) 0.0427(6) Uani 1 1 d . . . . .
H17 H -0.407889 0.522081 0.110046 0.051 Uiso 1 1 calc R . . . .
C18 C -0.3456(4) 0.7466(3) 0.1719(2) 0.0433(6) Uani 1 1 d . . . . .
H18 H -0.461913 0.785965 0.172451 0.052 Uiso 1 1 calc R . . . .
C19 C -0.2050(3) 0.8457(3) 0.20895(17) 0.0375(5) Uani 1 1 d . . . . .
H19 H -0.226921 0.951314 0.234777 0.045 Uiso 1 1 calc R . . . .
C20 C 0.1929(4) 0.5677(4) 0.1669(3) 0.0585(8) Uani 1 1 d . . . . .
H20A H 0.230272 0.578196 0.107463 0.088 Uiso 1 1 calc GR . . . .
H20B H 0.197885 0.452118 0.181677 0.088 Uiso 1 1 calc GR . . . .
H20C H 0.270439 0.632748 0.209794 0.088 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 O1 1.9891(15) 2_676 ?
Cu1 O1 1.9892(15) . ?
Cu1 O2 2.4880(18) . ?
Cu1 O2 2.4880(18) 2_676 ?
Cu1 N1 2.005(2) 2_676 ?
Cu1 N1 2.005(2) . ?
Cl1 C16 1.742(3) . ?
O1 C7 1.287(3) . ?
O2 C7 1.247(3) . ?
O3 C6 1.213(4) . ?
N1 C1 1.328(3) . ?
N1 C5 1.331(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C6 1.342(4) . ?
N3 H3 0.8600 . ?
N3 C9 1.379(3) . ?
N3 C14 1.436(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.373(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(4) . ?
C3 C4 1.384(4) . ?
C3 C6 1.510(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(4) . ?
C5 H5 0.9300 . ?
C7 C8 1.494(3) . ?
C8 C9 1.414(3) . ?
C8 C13 1.396(4) . ?
C9 C10 1.408(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.365(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.391(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.372(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.400(4) . ?
C14 C19 1.377(4) . ?
C15 C16 1.393(4) . ?
C15 C20 1.498(4) . ?
C16 C17 1.371(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.373(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(4) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
O1 Cu1 O1 180.0 2_676 . ?
O1 Cu1 O2 57.65(6) . . ?
O1 Cu1 O2 122.35(6) . 2_676 ?
O1 Cu1 O2 122.34(6) 2_676 . ?
O1 Cu1 O2 57.66(6) 2_676 2_676 ?
O1 Cu1 N1 90.02(7) 2_676 2_676 ?
O1 Cu1 N1 89.98(7) . 2_676 ?
O1 Cu1 N1 90.02(7) . . ?
O1 Cu1 N1 89.98(7) 2_676 . ?
O2 Cu1 O2 180.0 2_676 . ?
N1 Cu1 O2 93.49(7) 2_676 . ?
N1 Cu1 O2 93.49(7) . 2_676 ?
N1 Cu1 O2 86.51(7) 2_676 2_676 ?
N1 Cu1 O2 86.51(7) . . ?
N1 Cu1 N1 180.0 2_676 . ?
C7 O1 Cu1 101.68(14) . . ?
C7 O2 Cu1 79.84(14) . . ?
C1 N1 Cu1 117.99(16) . . ?
C1 N1 C5 118.0(2) . . ?
C5 N1 Cu1 123.97(18) . . ?
H2A N2 H2B 120.0 . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
C9 N3 H3 118.7 . . ?
C9 N3 C14 122.69(19) . . ?
C14 N3 H3 118.7 . . ?
N1 C1 H1 118.3 . . ?
N1 C1 C2 123.4(2) . . ?
C2 C1 H1 118.3 . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.0(2) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C6 117.3(2) . . ?
C4 C3 C2 117.7(2) . . ?
C4 C3 C6 125.0(2) . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 122.4(2) . . ?
N1 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
O3 C6 N2 122.9(3) . . ?
O3 C6 C3 120.2(3) . . ?
N2 C6 C3 116.9(2) . . ?
O1 C7 C8 118.7(2) . . ?
O2 C7 O1 120.7(2) . . ?
O2 C7 C8 120.5(2) . . ?
C9 C8 C7 123.3(2) . . ?
C13 C8 C7 118.1(2) . . ?
C13 C8 C9 118.4(2) . . ?
N3 C9 C8 121.8(2) . . ?
N3 C9 C10 119.7(2) . . ?
C10 C9 C8 118.5(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.0(2) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 120.7 . . ?
C13 C12 C11 118.6(2) . . ?
C13 C12 H12 120.7 . . ?
C8 C13 H13 118.8 . . ?
C12 C13 C8 122.5(2) . . ?
C12 C13 H13 118.8 . . ?
C15 C14 N3 120.8(2) . . ?
C19 C14 N3 117.7(2) . . ?
C19 C14 C15 121.5(2) . . ?
C14 C15 C20 121.9(2) . . ?
C16 C15 C14 115.9(2) . . ?
C16 C15 C20 122.2(3) . . ?
C15 C16 Cl1 119.0(2) . . ?
C17 C16 Cl1 117.6(2) . . ?
C17 C16 C15 123.5(2) . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 118.9(2) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.0(2) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 C18 120.2(2) . . ?
C14 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
N2 H2B O2 0.86 2.13 2.948(3) 159.9 1_545 yes
N3 H3 O1 0.86 2.02 2.656(2) 130.3 . yes
C4 H4 O2 0.93 2.35 3.224(3) 155.8 1_545 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C7 O2 -3.6(2) . . . . ?
Cu1 O1 C7 C8 174.26(16) . . . . ?
Cu1 O2 C7 O1 2.88(19) . . . . ?
Cu1 O2 C7 C8 -175.0(2) . . . . ?
Cu1 N1 C1 C2 -179.1(2) . . . . ?
Cu1 N1 C5 C4 179.8(2) . . . . ?
Cl1 C16 C17 C18 179.9(2) . . . . ?
O1 C7 C8 C9 -2.5(3) . . . . ?
O1 C7 C8 C13 -178.4(2) . . . . ?
O2 C7 C8 C9 175.4(2) . . . . ?
O2 C7 C8 C13 -0.5(3) . . . . ?
N1 C1 C2 C3 -0.6(4) . . . . ?
N3 C9 C10 C11 178.8(2) . . . . ?
N3 C14 C15 C16 179.8(2) . . . . ?
N3 C14 C15 C20 -0.8(4) . . . . ?
N3 C14 C19 C18 -180.0(2) . . . . ?
C1 N1 C5 C4 1.3(4) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C1 C2 C3 C6 -178.9(2) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C2 C3 C6 O3 -3.6(4) . . . . ?
C2 C3 C6 N2 175.8(2) . . . . ?
C3 C4 C5 N1 -1.1(4) . . . . ?
C4 C3 C6 O3 176.6(3) . . . . ?
C4 C3 C6 N2 -4.0(4) . . . . ?
C5 N1 C1 C2 -0.4(4) . . . . ?
C6 C3 C4 C5 179.7(2) . . . . ?
C7 C8 C9 N3 6.2(4) . . . . ?
C7 C8 C9 C10 -174.6(2) . . . . ?
C7 C8 C13 C12 175.1(2) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C9 N3 C14 C15 75.7(3) . . . . ?
C9 N3 C14 C19 -104.3(3) . . . . ?
C9 C8 C13 C12 -1.1(4) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C10 C11 C12 C13 1.2(4) . . . . ?
C11 C12 C13 C8 -0.2(4) . . . . ?
C13 C8 C9 N3 -177.8(2) . . . . ?
C13 C8 C9 C10 1.4(3) . . . . ?
C14 N3 C9 C8 -172.2(2) . . . . ?
C14 N3 C9 C10 8.6(4) . . . . ?
C14 C15 C16 Cl1 -179.44(19) . . . . ?
C14 C15 C16 C17 -0.2(4) . . . . ?
C15 C14 C19 C18 -0.1(4) . . . . ?
C15 C16 C17 C18 0.7(4) . . . . ?
C16 C17 C18 C19 -0.8(4) . . . . ?
C17 C18 C19 C14 0.5(4) . . . . ?
C19 C14 C15 C16 -0.1(4) . . . . ?
C19 C14 C15 C20 179.3(3) . . . . ?
C20 C15 C16 Cl1 1.2(4) . . . . ?
C20 C15 C16 C17 -179.6(3) . . . . ?

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

data_4
_database_code_depnum_ccdc_archive 'CCDC 1943969'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2019-07-29 deposited with the CCDC.	2020-06-24 downloaded from the CCDC.
;
_audit_creation_date             2019-03-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C38 H32 Cl2 Cu N8 O6'
_chemical_formula_sum            'C38 H32 Cl2 Cu N8 O6'
_chemical_formula_weight         831.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

_cell_length_a                   7.9504(4)
_cell_length_b                   11.2409(5)
_cell_length_c                   11.5631(5)
_cell_angle_alpha                111.459(3)
_cell_angle_beta                 107.655(4)
_cell_angle_gamma                96.108(4)
_cell_volume                     888.50(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    20906
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.68
_cell_measurement_theta_min      4.42
_shelx_estimated_absorpt_T_max   0.852
_shelx_estimated_absorpt_T_min   0.682
_exptl_absorpt_coefficient_mu    2.768
_exptl_absorpt_correction_T_max  0.501
_exptl_absorpt_correction_T_min  0.171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             427
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14685
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.423
_diffrn_reflns_theta_min         4.359
_diffrn_ambient_temperature      100
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari with Xenocs Genix3D Cu HF'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2912
_reflns_number_total             3347
_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       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction        
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.84, Darmstadt 2018
;
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2011 (Burla et al., 2007)'
_refine_diff_density_max         0.857
_refine_diff_density_min         -0.773
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0940P)²+0.3522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1283
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C1(H1), C2(H2), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
 C17(H17), C18(H18), C19(H19)
2.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.000000 0.000000 0.500000 0.01605(17) Uani 1 2 d S T P . .
Cl1 Cl 1.32109(9) 0.37388(6) 0.12906(6) 0.02766(19) Uani 1 1 d . . . . .
O1 O 1.0769(2) 0.18905(15) 0.53744(16) 0.0179(4) Uani 1 1 d . . . . .
O2 O 0.9708(2) 0.17698(17) 0.68934(17) 0.0213(4) Uani 1 1 d . . . . .
O3 O 0.2299(2) 0.00918(17) 0.02331(16) 0.0206(4) Uani 1 1 d . . . . .
N1 N 0.7539(3) -0.01438(18) 0.37417(19) 0.0167(4) Uani 1 1 d . . . . .
N2 N 0.0788(3) -0.0793(2) 0.1209(2) 0.0194(4) Uani 1 1 d . . . . .
H2A H -0.028213 -0.081045 0.067605 0.023 Uiso 1 1 calc R . . . .
H2B H 0.086145 -0.108309 0.182985 0.023 Uiso 1 1 calc R . . . .
N3 N 1.1773(3) 0.43059(19) 0.5457(2) 0.0189(4) Uani 1 1 d . . . . .
H3 H 1.133003 0.344865 0.499790 0.023 Uiso 1 1 calc R . . . .
N4 N 1.2186(3) 0.6105(2) 0.7437(2) 0.0230(5) Uani 1 1 d . . . . .
C1 C 0.7352(3) 0.0376(2) 0.2848(3) 0.0222(5) Uani 1 1 d . . . . .
H1 H 0.841570 0.080664 0.280928 0.027 Uiso 1 1 calc R . . . .
C2 C 0.5671(3) 0.0310(2) 0.1983(2) 0.0208(5) Uani 1 1 d . . . . .
H2 H 0.558984 0.068344 0.135762 0.025 Uiso 1 1 calc R . . . .
C3 C 0.4105(3) -0.0305(2) 0.2030(2) 0.0167(5) Uani 1 1 d . . . . .
C4 C 0.4293(3) -0.0855(2) 0.2949(2) 0.0202(5) Uani 1 1 d . . . . .
H4 H 0.325027 -0.128741 0.300930 0.024 Uiso 1 1 calc R . . . .
C5 C 0.6026(3) -0.0760(2) 0.3774(2) 0.0207(5) Uani 1 1 d . . . . .
H5 H 0.614810 -0.114828 0.438978 0.025 Uiso 1 1 calc R . . . .
C6 C 0.2294(3) -0.0330(2) 0.1077(2) 0.0179(5) Uani 1 1 d . . . . .
C7 C 1.0472(3) 0.2454(2) 0.6462(2) 0.0173(5) Uani 1 1 d . . . . .
C8 C 1.1089(3) 0.3914(2) 0.7213(2) 0.0183(5) Uani 1 1 d . . . . .
C9 C 1.1690(3) 0.4794(2) 0.6708(2) 0.0186(5) Uani 1 1 d . . . . .
C11 C 1.2177(4) 0.6572(3) 0.8678(3) 0.0275(6) Uani 1 1 d . . . . .
H11 H 1.255010 0.750038 0.918981 0.033 Uiso 1 1 calc R . . . .
C12 C 1.1667(4) 0.5807(3) 0.9268(3) 0.0280(6) Uani 1 1 d . . . . .
H12 H 1.170693 0.618487 1.016069 0.034 Uiso 1 1 calc R . . . .
C13 C 1.1091(3) 0.4456(3) 0.8497(3) 0.0233(5) Uani 1 1 d . . . . .
H13 H 1.069074 0.389456 0.885670 0.028 Uiso 1 1 calc R . . . .
C14 C 1.2440(3) 0.4936(2) 0.4782(2) 0.0181(5) Uani 1 1 d . . . . .
C15 C 1.2463(3) 0.4107(2) 0.3529(2) 0.0194(5) Uani 1 1 d . . . . .
C16 C 1.3132(3) 0.4705(2) 0.2843(2) 0.0206(5) Uani 1 1 d . . . . .
C17 C 1.3759(3) 0.6059(3) 0.3328(3) 0.0237(5) Uani 1 1 d . . . . .
H17 H 1.421854 0.643575 0.283812 0.028 Uiso 1 1 calc R . . . .
C18 C 1.3696(3) 0.6840(2) 0.4544(3) 0.0228(5) Uani 1 1 d . . . . .
H18 H 1.410193 0.777067 0.488685 0.027 Uiso 1 1 calc R . . . .
C19 C 1.3055(3) 0.6303(2) 0.5278(3) 0.0208(5) Uani 1 1 d . . . . .
H19 H 1.303238 0.686229 0.611647 0.025 Uiso 1 1 calc R . . . .
C20 C 1.1776(4) 0.2636(2) 0.2971(3) 0.0247(5) Uani 1 1 d . . . . .
H20A H 1.249408 0.230755 0.358768 0.037 Uiso 1 1 calc GR . . . .
H20B H 1.189327 0.222119 0.210146 0.037 Uiso 1 1 calc GR . . . .
H20C H 1.049389 0.242015 0.286099 0.037 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 O1 1.9917(16) 2_756 ?
Cu1 O1 1.9917(16) . ?
Cu1 O2 2.4544(17) 2_756 ?
Cu1 O2 2.4544(17) . ?
Cu1 N1 2.0014(19) . ?
Cu1 N1 2.0015(19) 2_756 ?
Cl1 C16 1.750(2) . ?
O1 C7 1.291(3) . ?
O2 C7 1.255(3) . ?
O3 C6 1.232(3) . ?
N1 C1 1.342(3) . ?
N1 C5 1.340(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C6 1.328(3) . ?
N3 H3 0.8800 . ?
N3 C9 1.373(3) . ?
N3 C14 1.402(3) . ?
N4 C9 1.344(3) . ?
N4 C11 1.338(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.380(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(3) . ?
C3 C4 1.392(3) . ?
C3 C6 1.515(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(3) . ?
C5 H5 0.9500 . ?
C7 C8 1.488(3) . ?
C8 C9 1.427(3) . ?
C8 C13 1.383(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.376(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.414(3) . ?
C14 C19 1.399(3) . ?
C15 C16 1.391(3) . ?
C15 C20 1.504(3) . ?
C16 C17 1.386(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.378(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.384(3) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
O1 Cu1 O1 180.0 2_756 . ?
O1 Cu1 O2 58.36(6) . . ?
O1 Cu1 O2 121.64(6) 2_756 . ?
O1 Cu1 O2 121.64(6) . 2_756 ?
O1 Cu1 O2 58.36(6) 2_756 2_756 ?
O1 Cu1 N1 89.52(7) 2_756 . ?
O1 Cu1 N1 90.48(7) . . ?
O1 Cu1 N1 90.48(7) 2_756 2_756 ?
O1 Cu1 N1 89.52(7) . 2_756 ?
O2 Cu1 O2 180.0 2_756 . ?
N1 Cu1 O2 93.00(7) 2_756 2_756 ?
N1 Cu1 O2 87.00(7) 2_756 . ?
N1 Cu1 O2 87.00(7) . 2_756 ?
N1 Cu1 O2 93.00(7) . . ?
N1 Cu1 N1 180.00(12) . 2_756 ?
C7 O1 Cu1 100.73(14) . . ?
C7 O2 Cu1 80.59(14) . . ?
C1 N1 Cu1 121.18(16) . . ?
C5 N1 Cu1 120.76(16) . . ?
C5 N1 C1 118.1(2) . . ?
H2A N2 H2B 120.0 . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
C9 N3 H3 114.4 . . ?
C9 N3 C14 131.2(2) . . ?
C14 N3 H3 114.4 . . ?
C11 N4 C9 118.3(2) . . ?
N1 C1 H1 118.8 . . ?
N1 C1 C2 122.4(2) . . ?
C2 C1 H1 118.8 . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.7(2) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 118.1(2) . . ?
C2 C3 C6 117.6(2) . . ?
C4 C3 C6 124.3(2) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 122.9(2) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
O3 C6 N2 123.7(2) . . ?
O3 C6 C3 118.3(2) . . ?
N2 C6 C3 118.0(2) . . ?
O1 C7 C8 119.4(2) . . ?
O2 C7 O1 120.0(2) . . ?
O2 C7 C8 120.6(2) . . ?
C9 C8 C7 124.8(2) . . ?
C13 C8 C7 117.5(2) . . ?
C13 C8 C9 117.6(2) . . ?
N3 C9 C8 120.1(2) . . ?
N4 C9 N3 118.6(2) . . ?
N4 C9 C8 121.3(2) . . ?
N4 C11 H11 117.6 . . ?
N4 C11 C12 124.8(2) . . ?
C12 C11 H11 117.6 . . ?
C11 C12 H12 121.6 . . ?
C11 C12 C13 116.8(2) . . ?
C13 C12 H12 121.6 . . ?
C8 C13 C12 121.1(2) . . ?
C8 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
N3 C14 C15 116.3(2) . . ?
C19 C14 N3 123.8(2) . . ?
C19 C14 C15 120.0(2) . . ?
C14 C15 C20 120.6(2) . . ?
C16 C15 C14 117.5(2) . . ?
C16 C15 C20 121.9(2) . . ?
C15 C16 Cl1 119.93(19) . . ?
C17 C16 Cl1 116.92(18) . . ?
C17 C16 C15 123.2(2) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 C16 117.9(2) . . ?
C18 C17 H17 121.0 . . ?
C17 C18 H18 119.2 . . ?
C17 C18 C19 121.6(2) . . ?
C19 C18 H18 119.2 . . ?
C14 C19 H19 120.1 . . ?
C18 C19 C14 119.8(2) . . ?
C18 C19 H19 120.1 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
N2 H2A O3 0.88 2.05 2.884(3) 157.8 2 yes
N2 H2B O2 0.88 2.04 2.893(3) 164.3 2_656 yes
N3 H3 O1 0.88 1.99 2.706(2) 137.4 . yes

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1943967'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2019-07-29 deposited with the CCDC.	2020-06-24 downloaded from the CCDC.
;
_audit_creation_date             2019-03-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C40 H32 Cl4 Cu N6 O6'
_chemical_formula_sum            'C40 H32 Cl4 Cu N6 O6'
_chemical_formula_weight         898.05
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

_cell_length_a                   15.1963(11)
_cell_length_b                   7.4203(5)
_cell_length_c                   17.8011(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.924(5)
_cell_angle_gamma                90
_cell_volume                     1970.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    23670
_cell_measurement_temperature    295
_cell_measurement_theta_max      71.56
_cell_measurement_theta_min      3.63
_shelx_estimated_absorpt_T_max   0.779
_shelx_estimated_absorpt_T_min   0.493
_exptl_absorpt_coefficient_mu    3.745
_exptl_absorpt_correction_T_max  0.548
_exptl_absorpt_correction_T_min  0.512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light brown'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             918
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23764
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.377
_diffrn_reflns_theta_min         3.511
_diffrn_ambient_temperature      295
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2822
_reflns_number_total             3786
_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       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_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         0.725
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3786
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      0.950
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0875P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1254
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C1(H1), C2(H2), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C17(H17), C18(H18)
2.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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 0.500000 0.500000 0.500000 0.03606(17) Uani 1 2 d S T P . .
Cl1 Cl 0.13979(8) 0.55008(13) 0.36980(6) 0.0876(3) Uani 1 1 d . . . . .
Cl2 Cl 0.20454(10) 1.07364(19) 0.58176(7) 0.1106(4) Uani 1 1 d . . . . .
O1 O 0.38756(10) 0.5558(2) 0.52742(10) 0.0417(4) Uani 1 1 d . . . . .
O2 O 0.44404(12) 0.3946(3) 0.62897(12) 0.0549(5) Uani 1 1 d . . . . .
O3 O 0.24118(12) -0.1428(3) 0.27191(11) 0.0509(5) Uani 1 1 d . . . . .
N1 N 0.44432(13) 0.2742(3) 0.44190(12) 0.0393(5) Uani 1 1 d . . . . .
N2 N 0.36132(15) -0.3232(3) 0.30517(14) 0.0537(6) Uani 1 1 d . . . . .
H2A H 0.335428 -0.411942 0.278746 0.064 Uiso 1 1 calc R . . . .
H2B H 0.415128 -0.334944 0.330485 0.064 Uiso 1 1 calc R . . . .
N3 N 0.23287(16) 0.7111(4) 0.51559(14) 0.0614(7) Uani 1 1 d . . . . .
H3 H 0.281658 0.697302 0.498402 0.074 Uiso 1 1 calc R . . . .
C1 C 0.35476(16) 0.2592(4) 0.42007(15) 0.0455(6) Uani 1 1 d . . . . .
H1 H 0.318806 0.349437 0.434431 0.055 Uiso 1 1 calc R . . . .
C2 C 0.31398(16) 0.1175(4) 0.37772(15) 0.0441(6) Uani 1 1 d . . . . .
H2 H 0.251861 0.113351 0.363745 0.053 Uiso 1 1 calc R . . . .
C3 C 0.36568(16) -0.0190(3) 0.35593(14) 0.0374(5) Uani 1 1 d . . . . .
C4 C 0.45806(17) -0.0058(4) 0.37930(16) 0.0457(6) Uani 1 1 d . . . . .
H4 H 0.495260 -0.095837 0.366683 0.055 Uiso 1 1 calc R . . . .
C5 C 0.49398(16) 0.1404(4) 0.42093(16) 0.0446(6) Uani 1 1 d . . . . .
H5 H 0.555981 0.147488 0.435456 0.053 Uiso 1 1 calc R . . . .
C6 C 0.31805(16) -0.1674(3) 0.30689(14) 0.0405(6) Uani 1 1 d . . . . .
C7 C 0.38190(15) 0.4852(3) 0.59261(15) 0.0392(5) Uani 1 1 d . . . . .
C8 C 0.29788(16) 0.5170(3) 0.62166(14) 0.0385(5) Uani 1 1 d . . . . .
C9 C 0.22685(16) 0.6238(4) 0.58252(15) 0.0441(6) Uani 1 1 d . . . . .
C10 C 0.14932(19) 0.6383(5) 0.61431(18) 0.0588(8) Uani 1 1 d . . . . .
H10 H 0.101881 0.708524 0.589566 0.071 Uiso 1 1 calc R . . . .
C11 C 0.1418(2) 0.5531(5) 0.6798(2) 0.0634(8) Uani 1 1 d . . . . .
H11 H 0.089036 0.564143 0.698692 0.076 Uiso 1 1 calc R . . . .
C12 C 0.2110(2) 0.4500(5) 0.71903(18) 0.0608(8) Uani 1 1 d . . . . .
H12 H 0.205991 0.393088 0.764580 0.073 Uiso 1 1 calc R . . . .
C13 C 0.28780(19) 0.4335(4) 0.68901(16) 0.0511(7) Uani 1 1 d . . . . .
H13 H 0.334638 0.363612 0.715016 0.061 Uiso 1 1 calc R . . . .
C14 C 0.16634(17) 0.8210(4) 0.47272(16) 0.0497(7) Uani 1 1 d . . . . .
C15 C 0.11910(18) 0.7647(4) 0.40156(17) 0.0522(7) Uani 1 1 d . . . . .
C16 C 0.0586(2) 0.8752(5) 0.35375(18) 0.0593(8) Uani 1 1 d . . . . .
C17 C 0.0442(2) 1.0425(5) 0.3811(2) 0.0687(10) Uani 1 1 d . . . . .
H17 H 0.003742 1.118466 0.350527 0.082 Uiso 1 1 calc R . . . .
C18 C 0.0859(3) 1.1037(5) 0.4508(2) 0.0700(9) Uani 1 1 d . . . . .
H18 H 0.073217 1.217543 0.467757 0.084 Uiso 1 1 calc R . . . .
C19 C 0.1485(2) 0.9917(5) 0.49657(19) 0.0626(8) Uani 1 1 d . . . . .
C20 C 0.0149(3) 0.8148(8) 0.2759(2) 0.1022(15) Uani 1 1 d . . . . .
H20A H 0.059803 0.773833 0.248513 0.153 Uiso 1 1 calc GR . . . .
H20B H -0.017497 0.913582 0.248812 0.153 Uiso 1 1 calc GR . . . .
H20C H -0.025844 0.718035 0.280055 0.153 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 O1 1.9093(16) . ?
Cu1 O1 1.9093(16) 3_666 ?
Cu1 O2 2.710(2) . ?
Cu1 O2 2.710(2) 3_666 ?
Cu1 N1 2.064(2) 3_666 ?
Cu1 N1 2.064(2) . ?
Cl1 C15 1.738(3) . ?
Cl2 C19 1.704(4) . ?
O1 C7 1.291(3) . ?
O2 C7 1.237(3) . ?
O3 C6 1.229(3) . ?
N1 C1 1.347(3) . ?
N1 C5 1.342(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C6 1.333(3) . ?
N3 H3 0.8600 . ?
N3 C9 1.374(4) . ?
N3 C14 1.406(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.371(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(4) . ?
C3 C4 1.390(3) . ?
C3 C6 1.503(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.368(4) . ?
C5 H5 0.9300 . ?
C7 C8 1.484(4) . ?
C8 C9 1.412(3) . ?
C8 C13 1.383(4) . ?
C9 C10 1.404(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.349(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.396(4) . ?
C14 C19 1.379(5) . ?
C15 C16 1.395(4) . ?
C16 C17 1.367(5) . ?
C16 C20 1.488(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.360(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.402(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
O1 Cu1 O1 180.0 . 3_666 ?
O1 Cu1 O2 126.41(7) 3_666 . ?
O1 Cu1 O2 53.59(7) 3_666 3_666 ?
O1 Cu1 O2 53.59(7) . . ?
O1 Cu1 O2 126.41(7) . 3_666 ?
O1 Cu1 N1 89.86(8) . 3_666 ?
O1 Cu1 N1 90.14(8) 3_666 3_666 ?
O1 Cu1 N1 89.86(8) 3_666 . ?
O1 Cu1 N1 90.14(8) . . ?
O2 Cu1 O2 180.0 3_666 . ?
N1 Cu1 O2 88.54(7) 3_666 . ?
N1 Cu1 O2 88.54(7) . 3_666 ?
N1 Cu1 O2 91.46(7) 3_666 3_666 ?
N1 Cu1 O2 91.46(7) . . ?
N1 Cu1 N1 180.0 3_666 . ?
C7 O1 Cu1 110.91(14) . . ?
C7 O2 Cu1 74.39(16) . . ?
C1 N1 Cu1 120.49(17) . . ?
C5 N1 Cu1 122.75(16) . . ?
C5 N1 C1 116.7(2) . . ?
H2A N2 H2B 120.0 . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
C9 N3 H3 117.1 . . ?
C9 N3 C14 125.8(2) . . ?
C14 N3 H3 117.1 . . ?
N1 C1 H1 118.4 . . ?
N1 C1 C2 123.3(2) . . ?
C2 C1 H1 118.4 . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 117.4(2) . . ?
C2 C3 C6 117.6(2) . . ?
C4 C3 C6 125.0(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 123.3(2) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
O3 C6 N2 122.9(2) . . ?
O3 C6 C3 119.5(2) . . ?
N2 C6 C3 117.6(2) . . ?
O1 C7 C8 117.2(2) . . ?
O2 C7 O1 121.1(2) . . ?
O2 C7 C8 121.7(2) . . ?
C9 C8 C7 123.0(2) . . ?
C13 C8 C7 118.3(2) . . ?
C13 C8 C9 118.6(2) . . ?
N3 C9 C8 121.5(2) . . ?
N3 C9 C10 120.8(2) . . ?
C10 C9 C8 117.7(2) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.8(3) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.1(3) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 120.9 . . ?
C13 C12 C11 118.3(3) . . ?
C13 C12 H12 120.9 . . ?
C8 C13 H13 118.8 . . ?
C12 C13 C8 122.5(3) . . ?
C12 C13 H13 118.8 . . ?
C15 C14 N3 120.8(3) . . ?
C19 C14 N3 121.9(3) . . ?
C19 C14 C15 117.2(3) . . ?
C14 C15 Cl1 118.4(2) . . ?
C16 C15 Cl1 118.6(3) . . ?
C16 C15 C14 122.9(3) . . ?
C15 C16 C20 121.2(4) . . ?
C17 C16 C15 116.6(3) . . ?
C17 C16 C20 122.2(3) . . ?
C16 C17 H17 118.3 . . ?
C18 C17 C16 123.4(3) . . ?
C18 C17 H17 118.3 . . ?
C17 C18 H18 120.6 . . ?
C17 C18 C19 118.7(3) . . ?
C19 C18 H18 120.6 . . ?
C14 C19 Cl2 120.5(3) . . ?
C14 C19 C18 121.1(3) . . ?
C18 C19 Cl2 118.4(3) . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
N2 H2A O3 0.86 2.17 3.020(3) 170.4 2_545 yes
N2 H2B O2 0.86 2.17 3.015(3) 167.0 3_656 yes
N3 H3 O1 0.86 1.91 2.590(3) 135.1 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C7 O2 -0.1(3) . . . . ?
Cu1 O1 C7 C8 -179.98(16) . . . . ?
Cu1 O2 C7 O1 0.10(19) . . . . ?
Cu1 O2 C7 C8 179.9(2) . . . . ?
Cu1 N1 C1 C2 176.3(2) . . . . ?
Cu1 N1 C5 C4 -176.8(2) . . . . ?
Cl1 C15 C16 C17 179.8(2) . . . . ?
Cl1 C15 C16 C20 -2.3(4) . . . . ?
O1 C7 C8 C9 -2.0(4) . . . . ?
O1 C7 C8 C13 176.0(2) . . . . ?
O2 C7 C8 C9 178.2(2) . . . . ?
O2 C7 C8 C13 -3.8(4) . . . . ?
N1 C1 C2 C3 0.4(4) . . . . ?
N3 C9 C10 C11 179.7(3) . . . . ?
N3 C14 C15 Cl1 3.8(4) . . . . ?
N3 C14 C15 C16 -173.8(3) . . . . ?
N3 C14 C19 Cl2 -2.4(4) . . . . ?
N3 C14 C19 C18 175.9(3) . . . . ?
C1 N1 C5 C4 0.2(4) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C1 C2 C3 C6 -177.6(2) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C2 C3 C6 O3 18.6(4) . . . . ?
C2 C3 C6 N2 -159.7(3) . . . . ?
C3 C4 C5 N1 0.8(4) . . . . ?
C4 C3 C6 O3 -159.5(3) . . . . ?
C4 C3 C6 N2 22.2(4) . . . . ?
C5 N1 C1 C2 -0.8(4) . . . . ?
C6 C3 C4 C5 176.9(3) . . . . ?
C7 C8 C9 N3 -2.4(4) . . . . ?
C7 C8 C9 C10 177.6(3) . . . . ?
C7 C8 C13 C12 -177.7(3) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C9 N3 C14 C15 -110.0(4) . . . . ?
C9 N3 C14 C19 73.8(4) . . . . ?
C9 C8 C13 C12 0.3(4) . . . . ?
C9 C10 C11 C12 1.1(6) . . . . ?
C10 C11 C12 C13 -1.1(5) . . . . ?
C11 C12 C13 C8 0.4(5) . . . . ?
C13 C8 C9 N3 179.6(3) . . . . ?
C13 C8 C9 C10 -0.4(4) . . . . ?
C14 N3 C9 C8 -179.6(3) . . . . ?
C14 N3 C9 C10 0.4(5) . . . . ?
C14 C15 C16 C17 -2.6(5) . . . . ?
C14 C15 C16 C20 175.3(3) . . . . ?
C15 C14 C19 Cl2 -178.7(2) . . . . ?
C15 C14 C19 C18 -0.4(5) . . . . ?
C15 C16 C17 C18 0.5(5) . . . . ?
C16 C17 C18 C19 1.5(6) . . . . ?
C17 C18 C19 Cl2 176.8(3) . . . . ?
C17 C18 C19 C14 -1.5(5) . . . . ?
C19 C14 C15 Cl1 -179.9(2) . . . . ?
C19 C14 C15 C16 2.5(4) . . . . ?
C20 C16 C17 C18 -177.3(4) . . . . ?

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

data_5
_database_code_depnum_ccdc_archive 'CCDC 1943970'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2019-07-29 deposited with the CCDC.	2020-06-24 downloaded from the CCDC.
;
_audit_creation_date             2019-03-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C38 H28 Cu F6 N8 O6'
_chemical_formula_sum            'C38 H28 Cu F6 N8 O6'
_chemical_formula_weight         870.22
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.3686(3)
_cell_length_b                   11.4683(4)
_cell_length_c                   12.1866(5)
_cell_angle_alpha                110.961(3)
_cell_angle_beta                 104.284(3)
_cell_angle_gamma                103.325(3)
_cell_volume                     872.23(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    22555
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.55
_cell_measurement_theta_min      4.17
_shelx_estimated_absorpt_T_max   0.903
_shelx_estimated_absorpt_T_min   0.537
_exptl_absorpt_coefficient_mu    1.731
_exptl_absorpt_correction_T_max  0.639
_exptl_absorpt_correction_T_min  0.258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light brown'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             443
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14399
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.343
_diffrn_reflns_theta_min         4.168
_diffrn_ambient_temperature      100
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari with Xenocs Genix3D Cu HF'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2981
_reflns_number_total             3256
_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       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction        
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.84, Darmstadt 2018
;
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2011 (Burla et al., 2007)'
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.057
_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     268
_refine_ls_number_reflns         3256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0296
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0464P)²+0.6089P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0823
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C1(H1), C2(H2), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
 C15(H15), C17(H17), C18(H18), C19(H19)
2.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.000000 1.000000 0.500000 0.01137(11) Uani 1 2 d S T P . .
F1 F 0.74784(16) 0.78139(10) 0.98571(9) 0.0227(2) Uani 1 1 d . . . . .
F2 F 0.63895(18) 0.62416(11) 1.03574(10) 0.0278(3) Uani 1 1 d . . . . .
F3 F 0.95191(17) 0.70222(11) 1.06800(10) 0.0286(3) Uani 1 1 d . . . . .
O1 O 0.94322(17) 0.81181(11) 0.39691(10) 0.0139(2) Uani 1 1 d . . . . .
O2 O 0.84313(17) 0.80355(11) 0.55195(11) 0.0161(2) Uani 1 1 d . . . . .
O3 O 0.20697(18) 0.94053(13) 0.01193(11) 0.0203(3) Uani 1 1 d . . . . .
N1 N 0.7463(2) 0.98769(13) 0.38141(13) 0.0133(3) Uani 1 1 d . . . . .
N2 N 0.1080(2) 1.04443(14) 0.17060(13) 0.0166(3) Uani 1 1 d . . . . .
H2A H 0.003715 1.047659 0.119410 0.020 Uiso 1 1 calc R . . . .
H2B H 0.131883 1.077645 0.252079 0.020 Uiso 1 1 calc R . . . .
N3 N 0.7457(2) 0.56770(14) 0.56020(13) 0.0166(3) Uani 1 1 d . . . . .
H3 H 0.755088 0.651791 0.586959 0.020 Uiso 1 1 calc R . . . .
N4 N 0.7137(2) 0.38011(14) 0.38505(14) 0.0179(3) Uani 1 1 d . . . . .
C1 C 0.6893(3) 0.91794(16) 0.25597(16) 0.0163(3) Uani 1 1 d . . . . .
H1 H 0.765282 0.867084 0.223862 0.020 Uiso 1 1 calc R . . . .
C2 C 0.5240(3) 0.91758(17) 0.17206(16) 0.0168(3) Uani 1 1 d . . . . .
H2 H 0.489635 0.869289 0.083808 0.020 Uiso 1 1 calc R . . . .
C3 C 0.4083(2) 0.98873(16) 0.21822(16) 0.0140(3) Uani 1 1 d . . . . .
C4 C 0.4654(2) 1.05901(16) 0.34800(16) 0.0158(3) Uani 1 1 d . . . . .
H4 H 0.388610 1.107375 0.382817 0.019 Uiso 1 1 calc R . . . .
C5 C 0.6361(2) 1.05729(16) 0.42559(16) 0.0148(3) Uani 1 1 d . . . . .
H5 H 0.676868 1.107697 0.514141 0.018 Uiso 1 1 calc R . . . .
C6 C 0.2305(2) 0.98893(16) 0.12447(16) 0.0162(3) Uani 1 1 d . . . . .
C7 C 0.8681(2) 0.74594(16) 0.45054(15) 0.0136(3) Uani 1 1 d . . . . .
C8 C 0.8121(2) 0.59788(16) 0.38654(15) 0.0140(3) Uani 1 1 d . . . . .
C9 C 0.7560(2) 0.51232(16) 0.44272(16) 0.0148(3) Uani 1 1 d . . . . .
C11 C 0.7242(3) 0.32878(17) 0.27040(17) 0.0194(4) Uani 1 1 d . . . . .
H11 H 0.695600 0.235341 0.229942 0.023 Uiso 1 1 calc R . . . .
C12 C 0.7736(3) 0.40218(17) 0.20681(16) 0.0178(4) Uani 1 1 d . . . . .
H12 H 0.776347 0.360525 0.124694 0.021 Uiso 1 1 calc R . . . .
C13 C 0.8191(2) 0.53888(17) 0.26716(16) 0.0158(3) Uani 1 1 d . . . . .
H13 H 0.855273 0.592516 0.226510 0.019 Uiso 1 1 calc R . . . .
C14 C 0.7232(2) 0.51487(17) 0.64478(16) 0.0155(3) Uani 1 1 d . . . . .
C15 C 0.7445(2) 0.60643(17) 0.76379(16) 0.0164(3) Uani 1 1 d . . . . .
H15 H 0.767379 0.697240 0.780969 0.020 Uiso 1 1 calc R . . . .
C16 C 0.7326(2) 0.56607(17) 0.85667(16) 0.0167(3) Uani 1 1 d . . . . .
C17 C 0.6975(3) 0.43349(18) 0.83428(17) 0.0201(4) Uani 1 1 d . . . . .
H17 H 0.690772 0.406149 0.898574 0.024 Uiso 1 1 calc R . . . .
C18 C 0.6727(3) 0.34295(17) 0.71563(17) 0.0207(4) Uani 1 1 d . . . . .
H18 H 0.646574 0.251868 0.698376 0.025 Uiso 1 1 calc R . . . .
C19 C 0.6849(3) 0.38130(17) 0.62071(16) 0.0181(4) Uani 1 1 d . . . . .
H19 H 0.667278 0.316973 0.539980 0.022 Uiso 1 1 calc R . . . .
C20 C 0.7667(3) 0.66736(17) 0.98470(17) 0.0191(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 O1 1.9483(11) 2_776 ?
Cu1 O1 1.9483(11) . ?
Cu1 O2 2.6446(12) . ?
Cu1 O2 2.6446(12) 2_776 ?
Cu1 N1 2.0006(13) 2_776 ?
Cu1 N1 2.0006(13) . ?
F1 C20 1.343(2) . ?
F2 C20 1.347(2) . ?
F3 C20 1.352(2) . ?
O1 C7 1.282(2) . ?
O2 C7 1.258(2) . ?
O3 C6 1.230(2) . ?
N1 C1 1.344(2) . ?
N1 C5 1.339(2) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C6 1.340(2) . ?
N3 H3 0.8800 . ?
N3 C9 1.372(2) . ?
N3 C14 1.394(2) . ?
N4 C9 1.342(2) . ?
N4 C11 1.338(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.382(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(2) . ?
C3 C4 1.390(2) . ?
C3 C6 1.512(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(2) . ?
C5 H5 0.9500 . ?
C7 C8 1.494(2) . ?
C8 C9 1.427(2) . ?
C8 C13 1.388(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.397(2) . ?
C14 C19 1.397(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(2) . ?
C16 C17 1.393(2) . ?
C16 C20 1.491(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.382(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.392(2) . ?
C19 H19 0.9500 . ?

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
O1 Cu1 O1 180.0 2_776 . ?
O1 Cu1 O2 55.18(4) . . ?
O1 Cu1 O2 124.82(4) 2_776 . ?
O1 Cu1 O2 124.82(4) . 2_776 ?
O1 Cu1 O2 55.18(4) 2_776 2_776 ?
O1 Cu1 N1 90.75(5) 2_776 . ?
O1 Cu1 N1 89.25(5) . . ?
O1 Cu1 N1 89.25(5) 2_776 2_776 ?
O1 Cu1 N1 90.75(5) . 2_776 ?
O2 Cu1 O2 180.0 2_776 . ?
N1 Cu1 O2 97.57(5) 2_776 2_776 ?
N1 Cu1 O2 82.43(5) 2_776 . ?
N1 Cu1 O2 82.43(5) . 2_776 ?
N1 Cu1 O2 97.57(5) . . ?
N1 Cu1 N1 180.0 . 2_776 ?
C7 O1 Cu1 107.56(10) . . ?
C7 O2 Cu1 75.82(9) . . ?
C1 N1 Cu1 121.47(11) . . ?
C5 N1 Cu1 120.09(11) . . ?
C5 N1 C1 118.27(14) . . ?
H2A N2 H2B 120.0 . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
C9 N3 H3 114.2 . . ?
C9 N3 C14 131.65(14) . . ?
C14 N3 H3 114.2 . . ?
C11 N4 C9 117.73(15) . . ?
N1 C1 H1 118.8 . . ?
N1 C1 C2 122.33(15) . . ?
C2 C1 H1 118.8 . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.30(15) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C6 118.27(15) . . ?
C4 C3 C2 118.34(15) . . ?
C4 C3 C6 123.36(15) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.82(15) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 122.91(15) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
O3 C6 N2 123.72(15) . . ?
O3 C6 C3 119.23(15) . . ?
N2 C6 C3 117.04(15) . . ?
O1 C7 C8 116.65(14) . . ?
O2 C7 O1 121.43(15) . . ?
O2 C7 C8 121.92(15) . . ?
C9 C8 C7 123.60(14) . . ?
C13 C8 C7 119.07(15) . . ?
C13 C8 C9 117.31(15) . . ?
N3 C9 C8 118.60(15) . . ?
N4 C9 N3 119.01(15) . . ?
N4 C9 C8 122.39(15) . . ?
N4 C11 H11 117.7 . . ?
N4 C11 C12 124.54(16) . . ?
C12 C11 H11 117.7 . . ?
C11 C12 H12 121.2 . . ?
C11 C12 C13 117.58(16) . . ?
C13 C12 H12 121.2 . . ?
C8 C13 H13 119.8 . . ?
C12 C13 C8 120.44(16) . . ?
C12 C13 H13 119.8 . . ?
N3 C14 C15 115.60(15) . . ?
N3 C14 C19 125.69(16) . . ?
C19 C14 C15 118.70(16) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.59(15) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C17 121.18(16) . . ?
C15 C16 C20 119.32(15) . . ?
C17 C16 C20 119.45(16) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 C16 117.95(16) . . ?
C18 C17 H17 121.0 . . ?
C17 C18 H18 119.0 . . ?
C17 C18 C19 121.93(16) . . ?
C19 C18 H18 119.0 . . ?
C14 C19 H19 120.2 . . ?
C18 C19 C14 119.64(16) . . ?
C18 C19 H19 120.2 . . ?
F1 C20 F2 106.25(14) . . ?
F1 C20 F3 105.96(14) . . ?
F1 C20 C16 113.01(14) . . ?
F2 C20 F3 105.66(14) . . ?
F2 C20 C16 112.90(14) . . ?
F3 C20 C16 112.45(14) . . ?

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
N2 H2A O3 0.88 2.00 2.8769(18) 171.2 2_575 yes
N3 H3 O2 0.88 1.94 2.6789(18) 140.0 . yes

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 1943968'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2019-07-29 deposited with the CCDC.	2020-06-24 downloaded from the CCDC.
;
_audit_creation_date             2019-03-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H40 Cu N6 O6'
_chemical_formula_sum            'C42 H40 Cu N6 O6'
_chemical_formula_weight         788.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

_cell_length_a                   7.5432(2)
_cell_length_b                   8.0729(2)
_cell_length_c                   14.8265(3)
_cell_angle_alpha                86.028(2)
_cell_angle_beta                 85.211(2)
_cell_angle_gamma                89.102(2)
_cell_volume                     897.51(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    37504
_cell_measurement_temperature    295
_cell_measurement_theta_max      71.76
_cell_measurement_theta_min      3.00
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.866
_exptl_absorpt_coefficient_mu    1.352
_exptl_absorpt_correction_T_max  0.851
_exptl_absorpt_correction_T_min  0.847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             411
_exptl_crystal_size_max          0.11
_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  0.0477
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32730
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.256
_diffrn_reflns_theta_min         2.998
_diffrn_ambient_temperature      295
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2721
_reflns_number_total             3372
_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       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3372
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      0.936
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0620P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0883
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C5(H5), C4(H4), C2(H2), C1(H1), C10(H10), C11(H11), C12(H12),
 C13(H13), C17(H17), C18(H18), C19(H19)
2.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.000000 0.500000 0.500000 0.03410(13) Uani 1 2 d S T P . .
O1 O 0.15637(16) 0.51645(15) 0.38530(8) 0.0374(3) Uani 1 1 d . . . . .
O2 O -0.06884(17) 0.35767(16) 0.36380(9) 0.0416(3) Uani 1 1 d . . . . .
O3 O 0.6515(2) -0.0569(2) 0.63218(11) 0.0602(4) Uani 1 1 d . . . . .
N1 N 0.1466(2) 0.30716(18) 0.54623(10) 0.0365(3) Uani 1 1 d . . . . .
N2 N 0.4249(2) -0.2361(2) 0.66088(13) 0.0549(5) Uani 1 1 d . . . . .
H2A H 0.493878 -0.316721 0.677006 0.066 Uiso 1 1 calc R . . . .
H2B H 0.312242 -0.251607 0.661596 0.066 Uiso 1 1 calc R . . . .
N3 N 0.3925(2) 0.6019(2) 0.24731(10) 0.0413(4) Uani 1 1 d . . . . .
H3 H 0.377303 0.588136 0.305464 0.050 Uiso 1 1 calc R . . . .
C5 C 0.0780(3) 0.1622(2) 0.57933(14) 0.0427(4) Uani 1 1 d . . . . .
H5 H -0.044630 0.149063 0.582325 0.051 Uiso 1 1 calc R . . . .
C4 C 0.1815(3) 0.0314(2) 0.60924(14) 0.0456(5) Uani 1 1 d . . . . .
H4 H 0.128795 -0.068105 0.631777 0.055 Uiso 1 1 calc R . . . .
C3 C 0.3639(2) 0.0480(2) 0.60571(12) 0.0381(4) Uani 1 1 d . . . . .
C2 C 0.4341(3) 0.2001(2) 0.57288(13) 0.0427(4) Uani 1 1 d . . . . .
H2 H 0.555958 0.217702 0.570605 0.051 Uiso 1 1 calc R . . . .
C1 C 0.3222(3) 0.3244(2) 0.54378(14) 0.0439(4) Uani 1 1 d . . . . .
H1 H 0.371247 0.425496 0.521304 0.053 Uiso 1 1 calc R . . . .
C6 C 0.4929(3) -0.0867(3) 0.63467(13) 0.0451(5) Uani 1 1 d . . . . .
C7 C 0.0706(2) 0.4309(2) 0.33312(12) 0.0328(4) Uani 1 1 d . . . . .
C8 C 0.1355(2) 0.4260(2) 0.23625(11) 0.0307(4) Uani 1 1 d . . . . .
C9 C 0.2850(2) 0.5173(2) 0.19609(11) 0.0315(4) Uani 1 1 d . . . . .
C10 C 0.3238(2) 0.5160(2) 0.10205(12) 0.0378(4) Uani 1 1 d . . . . .
H10 H 0.420343 0.576047 0.074633 0.045 Uiso 1 1 calc R . . . .
C11 C 0.2232(3) 0.4284(2) 0.04952(13) 0.0418(4) Uani 1 1 d . . . . .
H11 H 0.250601 0.431593 -0.012896 0.050 Uiso 1 1 calc R . . . .
C12 C 0.0804(3) 0.3350(2) 0.08877(13) 0.0427(4) Uani 1 1 d . . . . .
H12 H 0.014027 0.272969 0.053378 0.051 Uiso 1 1 calc R . . . .
C13 C 0.0388(2) 0.3357(2) 0.18051(13) 0.0377(4) Uani 1 1 d . . . . .
H13 H -0.057476 0.273706 0.206582 0.045 Uiso 1 1 calc R . . . .
C14 C 0.5288(2) 0.7121(2) 0.20730(12) 0.0348(4) Uani 1 1 d . . . . .
C15 C 0.4882(2) 0.8699(2) 0.17017(13) 0.0388(4) Uani 1 1 d . . . . .
C16 C 0.6284(3) 0.9722(2) 0.13249(14) 0.0419(4) Uani 1 1 d . . . . .
C17 C 0.8016(2) 0.9128(2) 0.13336(14) 0.0448(5) Uani 1 1 d . . . . .
H17 H 0.894357 0.980647 0.108696 0.054 Uiso 1 1 calc R . . . .
C18 C 0.8398(2) 0.7571(2) 0.16952(14) 0.0454(5) Uani 1 1 d . . . . .
H18 H 0.957086 0.719551 0.168781 0.054 Uiso 1 1 calc R . . . .
C19 C 0.7030(2) 0.6559(2) 0.20717(13) 0.0398(4) Uani 1 1 d . . . . .
H19 H 0.727959 0.550259 0.232354 0.048 Uiso 1 1 calc R . . . .
C20 C 0.2986(3) 0.9301(3) 0.16984(18) 0.0572(6) Uani 1 1 d . . . . .
H20A H 0.261233 0.929819 0.109519 0.086 Uiso 1 1 calc GR . . . .
H20B H 0.289829 1.040830 0.189652 0.086 Uiso 1 1 calc GR . . . .
H20C H 0.223620 0.857925 0.210142 0.086 Uiso 1 1 calc GR . . . .
C21 C 0.5922(3) 1.1437(3) 0.09183(19) 0.0640(6) Uani 1 1 d . . . . .
H21A H 0.515055 1.137057 0.043926 0.096 Uiso 1 1 calc GR . . . .
H21B H 0.702329 1.193837 0.067823 0.096 Uiso 1 1 calc GR . . . .
H21C H 0.536224 1.209721 0.137745 0.096 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 O1 1.9849(12) . ?
Cu1 O1 1.9849(12) 2_566 ?
Cu1 O2 2.4865(13) . ?
Cu1 O2 2.4865(13) 2_566 ?
Cu1 N1 2.0101(15) . ?
Cu1 N1 2.0101(15) 2_566 ?
O1 C7 1.291(2) . ?
O2 C7 1.251(2) . ?
O3 C6 1.221(3) . ?
N1 C5 1.332(2) . ?
N1 C1 1.331(2) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C6 1.338(3) . ?
N3 H3 0.8600 . ?
N3 C9 1.375(2) . ?
N3 C14 1.434(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.374(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.381(3) . ?
C3 C2 1.385(3) . ?
C3 C6 1.512(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.371(3) . ?
C1 H1 0.9300 . ?
C7 C8 1.481(2) . ?
C8 C9 1.422(2) . ?
C8 C13 1.396(2) . ?
C9 C10 1.401(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.369(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.388(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.370(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.393(3) . ?
C14 C19 1.383(3) . ?
C15 C16 1.406(3) . ?
C15 C20 1.503(3) . ?
C16 C17 1.385(3) . ?
C16 C21 1.501(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.368(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(3) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
O1 Cu1 O1 180.00(6) . 2_566 ?
O1 Cu1 O2 57.68(4) . . ?
O1 Cu1 O2 122.32(4) 2_566 . ?
O1 Cu1 O2 57.68(4) 2_566 2_566 ?
O1 Cu1 O2 122.32(4) . 2_566 ?
O1 Cu1 N1 89.92(5) . . ?
O1 Cu1 N1 90.08(5) 2_566 . ?
O1 Cu1 N1 90.08(5) . 2_566 ?
O1 Cu1 N1 89.92(5) 2_566 2_566 ?
O2 Cu1 O2 180.0 2_566 . ?
N1 Cu1 O2 92.63(5) 2_566 2_566 ?
N1 Cu1 O2 87.37(5) 2_566 . ?
N1 Cu1 O2 92.63(5) . . ?
N1 Cu1 O2 87.37(5) . 2_566 ?
N1 Cu1 N1 180.0 . 2_566 ?
C7 O1 Cu1 102.08(10) . . ?
C7 O2 Cu1 80.11(10) . . ?
C5 N1 Cu1 123.70(13) . . ?
C1 N1 Cu1 118.47(12) . . ?
C1 N1 C5 117.82(16) . . ?
H2A N2 H2B 120.0 . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
C9 N3 H3 118.8 . . ?
C9 N3 C14 122.42(14) . . ?
C14 N3 H3 118.8 . . ?
N1 C5 H5 118.7 . . ?
N1 C5 C4 122.57(18) . . ?
C4 C5 H5 118.7 . . ?
C5 C4 H4 120.1 . . ?
C5 C4 C3 119.79(17) . . ?
C3 C4 H4 120.1 . . ?
C4 C3 C2 117.35(17) . . ?
C4 C3 C6 125.14(17) . . ?
C2 C3 C6 117.51(17) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 C3 119.41(17) . . ?
C1 C2 H2 120.3 . . ?
N1 C1 C2 123.04(17) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
O3 C6 N2 123.13(19) . . ?
O3 C6 C3 119.86(19) . . ?
N2 C6 C3 117.00(18) . . ?
O1 C7 C8 119.21(14) . . ?
O2 C7 O1 120.01(16) . . ?
O2 C7 C8 120.74(16) . . ?
C9 C8 C7 123.17(15) . . ?
C13 C8 C7 118.35(15) . . ?
C13 C8 C9 118.36(16) . . ?
N3 C9 C8 121.71(15) . . ?
N3 C9 C10 120.15(15) . . ?
C10 C9 C8 118.12(15) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.63(16) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.47(17) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 118.93(17) . . ?
C13 C12 H12 120.5 . . ?
C8 C13 H13 118.8 . . ?
C12 C13 C8 122.44(16) . . ?
C12 C13 H13 118.8 . . ?
C15 C14 N3 121.49(16) . . ?
C19 C14 N3 117.40(16) . . ?
C19 C14 C15 121.11(16) . . ?
C14 C15 C16 118.58(16) . . ?
C14 C15 C20 120.93(18) . . ?
C16 C15 C20 120.49(18) . . ?
C15 C16 C21 120.83(18) . . ?
C17 C16 C15 119.11(17) . . ?
C17 C16 C21 120.07(18) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.78(17) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.56(17) . . ?
C19 C18 H18 120.2 . . ?
C14 C19 H19 120.1 . . ?
C18 C19 C14 119.86(17) . . ?
C18 C19 H19 120.1 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
N2 H2B O2 0.86 2.11 2.934(2) 160.0 2_556 yes
N3 H3 O1 0.86 2.03 2.6585(19) 129.3 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C7 O2 -3.75(18) . . . . ?
Cu1 O1 C7 C8 173.98(12) . . . . ?
Cu1 O2 C7 O1 2.97(14) . . . . ?
Cu1 O2 C7 C8 -174.72(15) . . . . ?
Cu1 N1 C5 C4 178.97(15) . . . . ?
Cu1 N1 C1 C2 -179.40(15) . . . . ?
O1 C7 C8 C9 -2.7(2) . . . . ?
O1 C7 C8 C13 -178.66(15) . . . . ?
O2 C7 C8 C9 174.96(15) . . . . ?
O2 C7 C8 C13 -1.0(2) . . . . ?
N1 C5 C4 C3 0.2(3) . . . . ?
N3 C9 C10 C11 177.78(17) . . . . ?
N3 C14 C15 C16 179.61(16) . . . . ?
N3 C14 C15 C20 -0.6(3) . . . . ?
N3 C14 C19 C18 -179.96(17) . . . . ?
C5 N1 C1 C2 0.6(3) . . . . ?
C5 C4 C3 C2 1.1(3) . . . . ?
C5 C4 C3 C6 -178.80(18) . . . . ?
C4 C3 C2 C1 -1.5(3) . . . . ?
C4 C3 C6 O3 -177.1(2) . . . . ?
C4 C3 C6 N2 4.0(3) . . . . ?
C3 C2 C1 N1 0.7(3) . . . . ?
C2 C3 C6 O3 3.1(3) . . . . ?
C2 C3 C6 N2 -175.92(18) . . . . ?
C1 N1 C5 C4 -1.0(3) . . . . ?
C6 C3 C2 C1 178.41(17) . . . . ?
C7 C8 C9 N3 7.6(2) . . . . ?
C7 C8 C9 C10 -173.85(15) . . . . ?
C7 C8 C13 C12 174.63(16) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 N3 C14 C15 75.9(2) . . . . ?
C9 N3 C14 C19 -104.3(2) . . . . ?
C9 C8 C13 C12 -1.5(3) . . . . ?
C9 C10 C11 C12 -1.3(3) . . . . ?
C10 C11 C12 C13 1.9(3) . . . . ?
C11 C12 C13 C8 -0.5(3) . . . . ?
C13 C8 C9 N3 -176.43(16) . . . . ?
C13 C8 C9 C10 2.1(2) . . . . ?
C14 N3 C9 C8 -171.45(16) . . . . ?
C14 N3 C9 C10 10.1(3) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C14 C15 C16 C21 -179.80(19) . . . . ?
C15 C14 C19 C18 -0.1(3) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C17 C18 C19 C14 0.6(3) . . . . ?
C19 C14 C15 C16 -0.2(3) . . . . ?
C19 C14 C15 C20 179.55(18) . . . . ?
C20 C15 C16 C17 -179.62(19) . . . . ?
C20 C15 C16 C21 0.5(3) . . . . ?
C21 C16 C17 C18 -179.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
