# 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 2023

####################################################################### 
# 
# 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 2289146'
loop_
_audit_author_name
_audit_author_address
'Maksim shmelev'
;kurnakov institute of general and inorganic chemistry
Russia
;
_audit_update_record             
;
2023-11-28 deposited with the CCDC.	2023-12-01 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         ?
_chemical_formula_sum            'C22 H16 Cu F6 N6 O4'
_chemical_formula_weight         605.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   10.1267(17)
_cell_length_b                   10.9088(18)
_cell_length_c                   12.076(2)
_cell_angle_alpha                78.050(3)
_cell_angle_beta                 72.589(3)
_cell_angle_gamma                76.521(3)
_cell_volume                     1224.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1531
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      23.41

_exptl_crystal_description       prizm
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_F_000             610
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.980
_shelx_estimated_absorpt_T_min   0.799
_shelx_estimated_absorpt_T_max   0.828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.6130
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8632
_diffrn_reflns_av_unetI/netI     0.0819
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.402
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             6507
_reflns_number_gt                3864
_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       'Bruker SMART'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_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)+(0.0828P)²] 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         6507
_refine_ls_number_parameters     364
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.1708
_refine_ls_wR_factor_gt          0.1473
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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 0.72448(5) 0.75342(4) 0.73490(4) 0.03262(16) Uani 1 1 d . . . . .
O1 O 0.5445(3) 0.6685(3) 0.6954(3) 0.0554(8) Uani 1 1 d . . . . .
O2 O 0.4869(4) 0.5170(5) 0.8446(5) 0.132(2) Uani 1 1 d . . . . .
O3 O 0.8792(3) 0.8473(3) 0.7847(2) 0.0437(7) Uani 1 1 d . . . . .
O4 O 1.0321(4) 0.9215(4) 0.6218(3) 0.0808(12) Uani 1 1 d . . . . .
F1 F 0.4096(15) 0.5258(17) 0.6020(13) 0.208(8) Uani 0.5 1 d . . P A 1
F2 F 0.2793(8) 0.4845(7) 0.7807(9) 0.081(3) Uani 0.5 1 d . . P A 1
F3 F 0.2592(8) 0.6720(7) 0.6972(10) 0.076(3) Uani 0.5 1 d . . P A 1
F1A F 0.3264(12) 0.4619(12) 0.7305(10) 0.109(4) Uiso 0.5 1 d . . P A 2
F2A F 0.2481(14) 0.6525(13) 0.7436(10) 0.109(5) Uiso 0.5 1 d . . P A 2
F3A F 0.3819(10) 0.5961(8) 0.5911(9) 0.089(3) Uiso 0.5 1 d . . P A 2
F4 F 1.0616(3) 0.8563(3) 0.9027(3) 0.0847(10) Uani 1 1 d . . . . .
F5 F 0.9994(3) 1.0497(3) 0.8366(3) 0.0783(9) Uani 1 1 d . . . . .
F6 F 1.1943(3) 0.9417(3) 0.7479(3) 0.0709(9) Uani 1 1 d . . . . .
N1 N 0.8090(3) 0.5862(3) 0.8216(3) 0.0333(7) Uani 1 1 d . . . . .
N2 N 0.7480(4) 0.4844(3) 0.8664(4) 0.0598(11) Uani 1 1 d . . . . .
H2A H 0.6635 0.4802 0.8631 0.072 Uiso 1 1 calc R U . . .
N3 N 0.8495(3) 0.7104(3) 0.5759(3) 0.0376(7) Uani 1 1 d . . . . .
N4 N 0.9617(4) 0.7640(4) 0.5123(3) 0.0504(9) Uani 1 1 d . . . . .
H4A H 0.9945 0.8192 0.5358 0.061 Uiso 1 1 calc R U . . .
N5 N 0.5685(3) 0.8061(3) 0.8820(2) 0.0309(7) Uani 1 1 d . . . . .
N6 N 0.6324(3) 0.9300(3) 0.6637(2) 0.0301(7) Uani 1 1 d . . . . .
C1 C 0.4776(5) 0.5862(5) 0.7496(5) 0.0627(15) Uani 1 1 d . . . . .
C2 C 0.3594(6) 0.5705(5) 0.7043(5) 0.0681(15) Uani 1 1 d . . . . .
C3 C 0.9835(4) 0.8973(4) 0.7282(3) 0.0426(10) Uani 1 1 d . . . . .
C4 C 1.0616(4) 0.9358(4) 0.8021(4) 0.0471(10) Uani 1 1 d . . . . .
C5 C 0.8307(5) 0.3897(4) 0.9167(4) 0.0559(12) Uani 1 1 d . . . . .
H5A H 0.8085 0.3085 0.9535 0.067 Uiso 1 1 calc R U . . .
C6 C 0.9502(5) 0.4287(4) 0.9063(4) 0.0453(10) Uani 1 1 d . . . . .
H6A H 1.0289 0.3825 0.9339 0.054 Uiso 1 1 calc R U . . .
C7 C 0.9331(4) 0.5523(4) 0.8457(4) 0.0433(10) Uani 1 1 d . . . . .
H7A H 1.0016 0.6055 0.8245 0.052 Uiso 1 1 calc R U . . .
C8 C 0.8366(5) 0.6347(4) 0.5092(4) 0.0494(11) Uani 1 1 d . . . . .
H8A H 0.7659 0.5839 0.5307 0.059 Uiso 1 1 calc R U . . .
C9 C 0.9401(6) 0.6390(5) 0.4033(4) 0.0680(16) Uani 1 1 d . . . . .
H9A H 0.9538 0.5930 0.3409 0.082 Uiso 1 1 calc R U . . .
C10 C 1.0164(6) 0.7219(6) 0.4082(4) 0.0691(16) Uani 1 1 d . . . . .
H10A H 1.0952 0.7464 0.3486 0.083 Uiso 1 1 calc R U . . .
C11 C 0.6679(4) 0.9924(4) 0.5547(3) 0.0391(9) Uani 1 1 d . . . . .
H11A H 0.7472 0.9543 0.4993 0.047 Uiso 1 1 calc R U . . .
C12 C 0.5935(4) 1.1110(4) 0.5188(4) 0.0462(10) Uani 1 1 d . . . . .
H12A H 0.6236 1.1529 0.4409 0.055 Uiso 1 1 calc R U . . .
C13 C 0.4775(5) 1.1670(4) 0.5952(4) 0.0457(10) Uani 1 1 d . . . . .
H13A H 0.4252 1.2469 0.5704 0.055 Uiso 1 1 calc R U . . .
C14 C 0.4354(4) 1.1051(3) 0.7121(3) 0.0356(8) Uani 1 1 d . . . . .
C15 C 0.5176(4) 0.9863(3) 0.7410(3) 0.0297(8) Uani 1 1 d . . . . .
C16 C 0.4835(4) 0.9194(3) 0.8592(3) 0.0301(8) Uani 1 1 d . . . . .
C17 C 0.3175(4) 1.1554(4) 0.8005(4) 0.0440(10) Uani 1 1 d . . . . .
H17A H 0.2597 1.2341 0.7806 0.053 Uiso 1 1 calc R U . . .
C18 C 0.2862(4) 1.0937(4) 0.9119(4) 0.0414(9) Uani 1 1 d . . . . .
H18A H 0.2086 1.1307 0.9693 0.050 Uiso 1 1 calc R U . . .
C19 C 0.3689(4) 0.9734(4) 0.9439(3) 0.0352(8) Uani 1 1 d . . . . .
C20 C 0.3441(4) 0.9049(4) 1.0592(3) 0.0409(9) Uani 1 1 d . . . . .
H20A H 0.2684 0.9376 1.1203 0.049 Uiso 1 1 calc R U . . .
C21 C 0.4303(4) 0.7911(4) 1.0817(3) 0.0414(9) Uani 1 1 d . . . . .
H21A H 0.4141 0.7440 1.1585 0.050 Uiso 1 1 calc R U . . .
C22 C 0.5421(4) 0.7444(4) 0.9918(3) 0.0371(9) Uani 1 1 d . . . . .
H22A H 0.6016 0.6658 1.0092 0.045 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N3 2.037(3) . ?
Cu1 N1 2.043(3) . ?
Cu1 N6 2.068(3) . ?
Cu1 N5 2.074(3) . ?
Cu1 O3 2.331(3) . ?
Cu1 O1 2.429(3) . ?
O1 C1 1.211(5) . ?
O2 C1 1.252(6) . ?
O3 C3 1.250(5) . ?
O4 C3 1.227(5) . ?
F1 C2 1.335(12) . ?
F2 C2 1.392(8) . ?
F3 C2 1.324(9) . ?
F1A C2 1.258(12) . ?
F2A C2 1.297(14) . ?
F3A C2 1.298(11) . ?
F4 C4 1.338(5) . ?
F5 C4 1.344(5) . ?
F6 C4 1.318(5) . ?
N1 C7 1.326(5) . ?
N1 N2 1.334(4) . ?
N2 C5 1.334(5) . ?
N3 C8 1.318(5) . ?
N3 N4 1.351(5) . ?
N4 C10 1.342(6) . ?
N5 C22 1.335(4) . ?
N5 C16 1.360(4) . ?
N6 C11 1.336(4) . ?
N6 C15 1.363(4) . ?
C1 C2 1.513(8) . ?
C3 C4 1.527(6) . ?
C5 C6 1.338(6) . ?
C6 C7 1.394(6) . ?
C8 C9 1.390(6) . ?
C9 C10 1.338(8) . ?
C11 C12 1.391(5) . ?
C12 C13 1.362(6) . ?
C13 C14 1.417(5) . ?
C14 C15 1.406(5) . ?
C14 C17 1.428(5) . ?
C15 C16 1.442(5) . ?
C16 C19 1.401(5) . ?
C17 C18 1.353(6) . ?
C18 C19 1.430(6) . ?
C19 C20 1.417(5) . ?
C20 C21 1.369(6) . ?
C21 C22 1.395(5) . ?

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
N3 Cu1 N1 92.40(12) . . ?
N3 Cu1 N6 93.20(12) . . ?
N1 Cu1 N6 173.99(12) . . ?
N3 Cu1 N5 169.81(12) . . ?
N1 Cu1 N5 94.61(12) . . ?
N6 Cu1 N5 80.14(11) . . ?
N3 Cu1 O3 97.95(12) . . ?
N1 Cu1 O3 86.61(11) . . ?
N6 Cu1 O3 90.44(11) . . ?
N5 Cu1 O3 89.86(11) . . ?
N3 Cu1 O1 87.13(12) . . ?
N1 Cu1 O1 95.71(11) . . ?
N6 Cu1 O1 86.77(11) . . ?
N5 Cu1 O1 84.82(11) . . ?
O3 Cu1 O1 174.34(10) . . ?
C1 O1 Cu1 132.4(3) . . ?
C3 O3 Cu1 134.7(3) . . ?
C7 N1 N2 104.4(3) . . ?
C7 N1 Cu1 129.6(3) . . ?
N2 N1 Cu1 126.1(3) . . ?
C5 N2 N1 111.7(4) . . ?
C8 N3 N4 104.9(3) . . ?
C8 N3 Cu1 129.7(3) . . ?
N4 N3 Cu1 125.2(3) . . ?
C10 N4 N3 110.9(4) . . ?
C22 N5 C16 118.0(3) . . ?
C22 N5 Cu1 129.0(3) . . ?
C16 N5 Cu1 113.0(2) . . ?
C11 N6 C15 117.5(3) . . ?
C11 N6 Cu1 129.3(3) . . ?
C15 N6 Cu1 113.2(2) . . ?
O1 C1 O2 128.1(5) . . ?
O1 C1 C2 117.3(5) . . ?
O2 C1 C2 114.4(4) . . ?
F1A C2 F2A 108.0(9) . . ?
F1A C2 F3A 104.6(8) . . ?
F2A C2 F3A 104.2(8) . . ?
F3 C2 F1 110.4(10) . . ?
F3 C2 F2 99.8(6) . . ?
F1 C2 F2 106.4(10) . . ?
F1A C2 C1 116.2(8) . . ?
F2A C2 C1 108.7(8) . . ?
F3A C2 C1 114.3(6) . . ?
F3 C2 C1 116.0(6) . . ?
F1 C2 C1 111.1(8) . . ?
F2 C2 C1 112.3(5) . . ?
O4 C3 O3 129.7(4) . . ?
O4 C3 C4 114.8(4) . . ?
O3 C3 C4 115.5(3) . . ?
F6 C4 F5 107.4(4) . . ?
F6 C4 F4 106.5(4) . . ?
F5 C4 F4 104.0(4) . . ?
F6 C4 C3 113.7(4) . . ?
F5 C4 C3 111.7(4) . . ?
F4 C4 C3 112.9(4) . . ?
C6 C5 N2 108.3(4) . . ?
C5 C6 C7 104.3(4) . . ?
N1 C7 C6 111.4(4) . . ?
N3 C8 C9 111.1(5) . . ?
C10 C9 C8 105.3(4) . . ?
N4 C10 C9 107.8(4) . . ?
N6 C11 C12 122.7(4) . . ?
C13 C12 C11 120.1(3) . . ?
C12 C13 C14 119.5(4) . . ?
C15 C14 C13 116.5(3) . . ?
C15 C14 C17 118.9(3) . . ?
C13 C14 C17 124.6(4) . . ?
N6 C15 C14 123.7(3) . . ?
N6 C15 C16 116.6(3) . . ?
C14 C15 C16 119.7(3) . . ?
N5 C16 C19 123.5(3) . . ?
N5 C16 C15 116.8(3) . . ?
C19 C16 C15 119.6(3) . . ?
C18 C17 C14 121.6(4) . . ?
C17 C18 C19 120.6(4) . . ?
C16 C19 C20 116.8(4) . . ?
C16 C19 C18 119.6(3) . . ?
C20 C19 C18 123.6(4) . . ?
C21 C20 C19 119.3(4) . . ?
C20 C21 C22 120.0(3) . . ?
N5 C22 C21 122.4(4) . . ?

_refine_diff_density_max         0.772
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.083

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

data_01_a
_database_code_depnum_ccdc_archive 'CCDC 2289148'
loop_
_audit_author_name
_audit_author_address
'Maksim shmelev'
;kurnakov institute of general and inorganic chemistry
Russia
;
_audit_update_record             
;
2023-11-28 deposited with the CCDC.	2023-12-01 downloaded from the CCDC.
;
_audit_creation_date             2023-08-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 Cl Cu N6, Cl'
_chemical_formula_sum            'C18 H16 Cl2 Cu N6'
_chemical_formula_weight         450.81
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

_cell_length_a                   13.2386(14)
_cell_length_b                   8.9177(13)
_cell_length_c                   15.758(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.674(8)
_cell_angle_gamma                90
_cell_volume                     1851.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    668
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.79
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   0.866
_shelx_estimated_absorpt_T_min   0.808
_exptl_absorpt_coefficient_mu    1.485
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0561 before and 0.0442 after correction.
The Ratio of minimum to maximum transmission is 0.8756.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             916
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0925
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11821
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.498
_diffrn_reflns_theta_min         2.598
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3608
_reflns_number_total             5471
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.877
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         5471
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.030
_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)+(0.0277P)²+1.6047P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0979
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N4(H4), C16(H16), C7(H7), C9(H9), C4(H4A), C15(H15), C8(H8), C11(H11),
  C1(H1A), C6(H6), C5(H5), C2(H2), C3(H3), C14(H14), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.78682(2) 0.78547(4) 0.58013(2) 0.01409(10) Uani 1 1 d . . . . .
Cl1 Cl 0.85439(5) 0.99409(8) 0.48907(5) 0.02110(17) Uani 1 1 d . . . . .
Cl2 Cl 0.71167(5) 0.53095(9) 0.68305(4) 0.01905(17) Uani 1 1 d . . . . .
N5 N 0.70618(17) 0.9220(3) 0.65063(15) 0.0144(5) Uani 1 1 d . . . . .
N1 N 0.83180(17) 0.4796(3) 0.53038(15) 0.0152(5) Uani 1 1 d . . . . .
H1 H 0.8029 0.4469 0.5748 0.018 Uiso 1 1 calc R U . . .
N4 N 0.99843(17) 0.8670(3) 0.64510(16) 0.0169(5) Uani 1 1 d . . . . .
H4 H 1.0050 0.9169 0.5978 0.020 Uiso 1 1 calc R U . . .
N6 N 0.64671(17) 0.7504(2) 0.51772(15) 0.0133(5) Uani 1 1 d . . . . .
N3 N 0.91205(16) 0.7972(3) 0.66288(15) 0.0143(5) Uani 1 1 d . . . . .
N2 N 0.84532(16) 0.6253(3) 0.51233(14) 0.0129(5) Uani 1 1 d . . . . .
C16 C 0.6194(2) 0.6649(3) 0.45042(18) 0.0164(6) Uani 1 1 d . . . . .
H16 H 0.6708 0.6173 0.4222 0.020 Uiso 1 1 calc R U . . .
C17 C 0.5721(2) 0.8184(3) 0.55690(18) 0.0134(6) Uani 1 1 d . . . . .
C7 C 0.7386(2) 1.0136(3) 0.71401(19) 0.0199(6) Uani 1 1 d . . . . .
H7 H 0.8095 1.0212 0.7300 0.024 Uiso 1 1 calc R U . . .
C18 C 0.6045(2) 0.9124(3) 0.62824(18) 0.0135(6) Uani 1 1 d . . . . .
C9 C 0.5701(2) 1.0872(4) 0.73710(19) 0.0226(7) Uani 1 1 d . . . . .
H9 H 0.5244 1.1434 0.7675 0.027 Uiso 1 1 calc R U . . .
C4 C 0.9342(2) 0.7350(3) 0.73919(19) 0.0178(6) Uani 1 1 d . . . . .
H4A H 0.8881 0.6771 0.7682 0.021 Uiso 1 1 calc R U . . .
C15 C 0.5179(2) 0.6422(3) 0.4195(2) 0.0197(7) Uani 1 1 d . . . . .
H15 H 0.5011 0.5798 0.3713 0.024 Uiso 1 1 calc R U . . .
C10 C 0.5324(2) 0.9915(3) 0.67035(19) 0.0174(6) Uani 1 1 d . . . . .
C8 C 0.6721(2) 1.0994(4) 0.75816(19) 0.0228(7) Uani 1 1 d . . . . .
H8 H 0.6980 1.1654 0.8024 0.027 Uiso 1 1 calc R U . . .
C11 C 0.4266(2) 0.9728(4) 0.6414(2) 0.0214(7) Uani 1 1 d . . . . .
H11 H 0.3770 1.0244 0.6699 0.026 Uiso 1 1 calc R U . . .
C1 C 0.8681(2) 0.3905(3) 0.47172(19) 0.0173(6) Uani 1 1 d . . . . .
H1A H 0.8670 0.2840 0.4711 0.021 Uiso 1 1 calc R U . . .
C13 C 0.4690(2) 0.8034(3) 0.53007(18) 0.0162(6) Uani 1 1 d . . . . .
C6 C 1.0727(2) 0.8502(4) 0.7090(2) 0.0215(7) Uani 1 1 d . . . . .
H6 H 1.1396 0.8894 0.7107 0.026 Uiso 1 1 calc R U . . .
C5 C 1.0343(2) 0.7664(4) 0.7709(2) 0.0206(7) Uani 1 1 d . . . . .
H5 H 1.0682 0.7360 0.8240 0.025 Uiso 1 1 calc R U . . .
C2 C 0.9071(2) 0.4815(3) 0.41307(19) 0.0179(6) Uani 1 1 d . . . . .
H2 H 0.9383 0.4520 0.3639 0.021 Uiso 1 1 calc R U . . .
C3 C 0.8911(2) 0.6265(3) 0.44111(18) 0.0161(6) Uani 1 1 d . . . . .
H3 H 0.9104 0.7148 0.4130 0.019 Uiso 1 1 calc R U . . .
C14 C 0.4429(2) 0.7106(4) 0.4591(2) 0.0210(7) Uani 1 1 d . . . . .
H14 H 0.3736 0.6956 0.4388 0.025 Uiso 1 1 calc R U . . .
C12 C 0.3966(2) 0.8834(4) 0.5748(2) 0.0219(7) Uani 1 1 d . . . . .
H12 H 0.3262 0.8732 0.5571 0.026 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Cl1 2.5639(8) . ?
Cu1 N5 2.022(2) . ?
Cu1 N6 2.036(2) . ?
Cu1 N3 2.008(2) . ?
Cu1 N2 1.986(2) . ?
N5 C7 1.328(4) . ?
N5 C18 1.360(3) . ?
N1 H1 0.8800 . ?
N1 N2 1.346(3) . ?
N1 C1 1.343(4) . ?
N4 H4 0.8800 . ?
N4 N3 1.355(3) . ?
N4 C6 1.344(4) . ?
N6 C16 1.327(4) . ?
N6 C17 1.358(3) . ?
N3 C4 1.330(4) . ?
N2 C3 1.327(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.398(4) . ?
C17 C18 1.434(4) . ?
C17 C13 1.395(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.402(4) . ?
C18 C10 1.405(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.407(4) . ?
C9 C8 1.363(4) . ?
C4 H4A 0.9500 . ?
C4 C5 1.397(4) . ?
C15 H15 0.9500 . ?
C15 C14 1.367(4) . ?
C10 C11 1.440(4) . ?
C8 H8 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.346(4) . ?
C1 H1A 0.9500 . ?
C1 C2 1.369(4) . ?
C13 C14 1.407(4) . ?
C13 C12 1.435(4) . ?
C6 H6 0.9500 . ?
C6 C5 1.367(4) . ?
C5 H5 0.9500 . ?
C2 H2 0.9500 . ?
C2 C3 1.390(4) . ?
C3 H3 0.9500 . ?
C14 H14 0.9500 . ?
C12 H12 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
N5 Cu1 Cl1 95.91(7) . . ?
N5 Cu1 N6 81.52(9) . . ?
N6 Cu1 Cl1 101.11(7) . . ?
N3 Cu1 Cl1 90.82(7) . . ?
N3 Cu1 N5 93.36(9) . . ?
N3 Cu1 N6 167.41(9) . . ?
N2 Cu1 Cl1 92.55(7) . . ?
N2 Cu1 N5 169.54(9) . . ?
N2 Cu1 N6 90.85(9) . . ?
N2 Cu1 N3 92.63(9) . . ?
C7 N5 Cu1 129.4(2) . . ?
C7 N5 C18 118.1(3) . . ?
C18 N5 Cu1 112.49(18) . . ?
N2 N1 H1 124.4 . . ?
C1 N1 H1 124.4 . . ?
C1 N1 N2 111.2(2) . . ?
N3 N4 H4 124.3 . . ?
C6 N4 H4 124.3 . . ?
C6 N4 N3 111.4(3) . . ?
C16 N6 Cu1 129.6(2) . . ?
C16 N6 C17 117.8(3) . . ?
C17 N6 Cu1 112.38(18) . . ?
N4 N3 Cu1 123.30(19) . . ?
C4 N3 Cu1 131.2(2) . . ?
C4 N3 N4 105.3(2) . . ?
N1 N2 Cu1 120.90(18) . . ?
C3 N2 Cu1 133.2(2) . . ?
C3 N2 N1 105.5(2) . . ?
N6 C16 H16 118.7 . . ?
N6 C16 C15 122.6(3) . . ?
C15 C16 H16 118.7 . . ?
N6 C17 C18 116.3(2) . . ?
N6 C17 C13 123.6(3) . . ?
C13 C17 C18 120.1(3) . . ?
N5 C7 H7 118.8 . . ?
N5 C7 C8 122.5(3) . . ?
C8 C7 H7 118.8 . . ?
N5 C18 C17 116.9(2) . . ?
N5 C18 C10 123.2(3) . . ?
C10 C18 C17 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.0(3) . . ?
N3 C4 H4A 124.6 . . ?
N3 C4 C5 110.8(3) . . ?
C5 C4 H4A 124.6 . . ?
C16 C15 H15 120.3 . . ?
C14 C15 C16 119.5(3) . . ?
C14 C15 H15 120.3 . . ?
C18 C10 C9 116.8(3) . . ?
C18 C10 C11 118.5(3) . . ?
C9 C10 C11 124.7(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
N1 C1 H1A 126.3 . . ?
N1 C1 C2 107.4(3) . . ?
C2 C1 H1A 126.3 . . ?
C17 C13 C14 117.0(3) . . ?
C17 C13 C12 119.0(3) . . ?
C14 C13 C12 124.0(3) . . ?
N4 C6 H6 126.3 . . ?
N4 C6 C5 107.4(3) . . ?
C5 C6 H6 126.3 . . ?
C4 C5 H5 127.4 . . ?
C6 C5 C4 105.2(3) . . ?
C6 C5 H5 127.4 . . ?
C1 C2 H2 127.5 . . ?
C1 C2 C3 104.9(3) . . ?
C3 C2 H2 127.5 . . ?
N2 C3 C2 111.0(3) . . ?
N2 C3 H3 124.5 . . ?
C2 C3 H3 124.5 . . ?
C15 C14 C13 119.5(3) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C11 C12 C13 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 N5 C7 C8 -178.6(2) . . . . ?
Cu1 N5 C18 C17 -4.1(3) . . . . ?
Cu1 N5 C18 C10 177.2(2) . . . . ?
Cu1 N6 C16 C15 174.1(2) . . . . ?
Cu1 N6 C17 C18 5.8(3) . . . . ?
Cu1 N6 C17 C13 -175.6(2) . . . . ?
Cu1 N3 C4 C5 175.7(2) . . . . ?
Cu1 N2 C3 C2 -172.43(19) . . . . ?
N5 C7 C8 C9 1.4(5) . . . . ?
N5 C18 C10 C9 1.7(4) . . . . ?
N5 C18 C10 C11 -179.9(3) . . . . ?
N1 N2 C3 C2 0.0(3) . . . . ?
N1 C1 C2 C3 -0.1(3) . . . . ?
N4 N3 C4 C5 0.7(3) . . . . ?
N4 C6 C5 C4 0.3(3) . . . . ?
N6 C16 C15 C14 0.3(5) . . . . ?
N6 C17 C18 N5 -1.2(4) . . . . ?
N6 C17 C18 C10 177.5(2) . . . . ?
N6 C17 C13 C14 0.8(4) . . . . ?
N6 C17 C13 C12 -178.4(3) . . . . ?
N3 N4 C6 C5 0.1(3) . . . . ?
N3 C4 C5 C6 -0.7(3) . . . . ?
N2 N1 C1 C2 0.1(3) . . . . ?
C16 N6 C17 C18 -178.7(2) . . . . ?
C16 N6 C17 C13 -0.2(4) . . . . ?
C16 C15 C14 C13 0.3(5) . . . . ?
C17 N6 C16 C15 -0.4(4) . . . . ?
C17 C18 C10 C9 -177.0(3) . . . . ?
C17 C18 C10 C11 1.4(4) . . . . ?
C17 C13 C14 C15 -0.9(4) . . . . ?
C17 C13 C12 C11 0.4(4) . . . . ?
C7 N5 C18 C17 177.0(3) . . . . ?
C7 N5 C18 C10 -1.8(4) . . . . ?
C18 N5 C7 C8 0.2(4) . . . . ?
C18 C17 C13 C14 179.3(3) . . . . ?
C18 C17 C13 C12 0.1(4) . . . . ?
C18 C10 C11 C12 -0.9(4) . . . . ?
C9 C10 C11 C12 177.3(3) . . . . ?
C10 C9 C8 C7 -1.3(5) . . . . ?
C10 C11 C12 C13 0.0(5) . . . . ?
C8 C9 C10 C18 -0.1(4) . . . . ?
C8 C9 C10 C11 -178.4(3) . . . . ?
C1 N1 N2 Cu1 173.51(17) . . . . ?
C1 N1 N2 C3 -0.1(3) . . . . ?
C1 C2 C3 N2 0.0(3) . . . . ?
C13 C17 C18 N5 -179.8(3) . . . . ?
C13 C17 C18 C10 -1.0(4) . . . . ?
C6 N4 N3 Cu1 -175.97(19) . . . . ?
C6 N4 N3 C4 -0.5(3) . . . . ?
C14 C13 C12 C11 -178.7(3) . . . . ?
C12 C13 C14 C15 178.3(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_phencuHpzotf
_database_code_depnum_ccdc_archive 'CCDC 2289147'
loop_
_audit_author_name
_audit_author_address
'Maksim shmelev'
;kurnakov institute of general and inorganic chemistry
Russia
;
_audit_update_record             
;
2023-08-16 deposited with the CCDC.	2023-12-01 downloaded from the CCDC.
;
_audit_creation_date             2022-12-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_formula_moiety         'C20 H16 Cu F6 N6 O6 S2'
_chemical_formula_sum            'C20 H16 Cu F6 N6 O6 S2'
_chemical_formula_weight         678.055
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu 0.34125 1.28947 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19100 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.86690 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   16.084(3)
_cell_length_b                   11.6918(17)
_cell_length_c                   16.023(3)
_cell_angle_alpha                90
_cell_angle_beta                 119.823(3)
_cell_angle_gamma                90
_cell_volume                     2614.0(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3520
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.25
_cell_measurement_theta_min      2.28
_exptl_absorpt_coefficient_mu    1.087
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_description       prizm
_exptl_crystal_F_000             1367.617
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.9962
_diffrn_reflns_Laue_measured_fraction_max 0.9963
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11530
_diffrn_reflns_point_group_measured_fraction_full 0.9962
_diffrn_reflns_point_group_measured_fraction_max 0.9963
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.27
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.9962
_diffrn_measured_fraction_theta_max 0.9963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              19
_reflns_limit_h_min              -22
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                3011
_reflns_number_total             3786
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.7735
_refine_diff_density_min         -0.4340
_refine_diff_density_rms         0.0954
_refine_ls_d_res_high            0.7108
_refine_ls_d_res_low             8.9617
_refine_ls_goodness_of_fit_ref   1.0120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3786
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.0120
_refine_ls_shift/su_max          -0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0539P)²+0.3007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0966
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2a), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu1 Cu 0.0 0.15056(2) 0.25 0.02342(10) Uani 1.000000 2 S T P
S1 S -0.03382(3) 0.17573(3) 0.46275(3) 0.02642(11) Uani 1.000000 1 . . .
O1 O 0.01048(10) 0.14864(10) 0.40605(10) 0.0335(3) Uani 1.000000 1 . . .
O2 O -0.13620(11) 0.17339(12) 0.41176(12) 0.0449(4) Uani 1.000000 1 . . .
O3 O 0.01276(11) 0.12305(12) 0.55672(10) 0.0406(3) Uani 1.000000 1 . . .
N1 N 0.09975(11) 0.02916(12) 0.30159(11) 0.0290(3) Uani 1.000000 1 . . .
N2 N 0.10689(12) -0.04387(13) 0.36967(12) 0.0338(4) Uani 1.000000 1 . . .
H2 H 0.07248(12) -0.03942(13) 0.39840(12) 0.0405(4) Uiso 1.000000 1 R . .
N3 N 0.09456(10) 0.28088(13) 0.30272(10) 0.0272(3) Uani 1.000000 1 . . .
F1 F -0.04370(14) 0.36635(11) 0.54136(11) 0.0701(5) Uani 1.000000 1 . . .
F2 F -0.04218(10) 0.38956(10) 0.41086(9) 0.0475(3) Uani 1.000000 1 . . .
F3 F 0.08737(13) 0.34512(12) 0.53821(14) 0.0798(6) Uani 1.000000 1 . . .
C1 C 0.16316(15) -0.00690(17) 0.27681(16) 0.0392(5) Uani 1.000000 1 . . .
H1 H 0.17426(15) 0.02787(17) 0.22964(16) 0.0471(5) Uiso 1.000000 1 R . .
C2 C 0.21072(16) -0.10339(19) 0.33063(17) 0.0483(5) Uani 1.000000 1 . . .
H2a H 0.25951(16) -0.14583(19) 0.32757(17) 0.0580(6) Uiso 1.000000 1 R . .
C3 C 0.17296(17) -0.12401(18) 0.38806(16) 0.0433(5) Uani 1.000000 1 . . .
H3 H 0.19031(17) -0.18454(18) 0.43328(16) 0.0519(6) Uiso 1.000000 1 R . .
C4 C 0.18934(15) 0.2777(2) 0.35713(16) 0.0424(5) Uani 1.000000 1 . . .
H4 H 0.22044(15) 0.2055(2) 0.37514(16) 0.0509(6) Uiso 1.000000 1 R . .
C5 C 0.24494(18) 0.3773(2) 0.3888(2) 0.0586(7) Uani 1.000000 1 . . .
H5 H 0.31265(18) 0.3726(2) 0.4278(2) 0.0703(8) Uiso 1.000000 1 R . .
C6 C 0.2008(2) 0.4806(2) 0.36315(18) 0.0581(7) Uani 1.000000 1 . . .
H6 H 0.2380(2) 0.5486(2) 0.38370(18) 0.0697(9) Uiso 1.000000 1 R . .
C7 C 0.10146(18) 0.48772(17) 0.30689(15) 0.0421(5) Uani 1.000000 1 . . .
C8 C 0.05084(13) 0.38357(15) 0.27845(12) 0.0277(4) Uani 1.000000 1 . . .
C9 C 0.0478(2) 0.59155(18) 0.27651(16) 0.0566(7) Uani 1.000000 1 . . .
H9 H 0.0809(2) 0.66252(18) 0.29442(16) 0.0679(9) Uiso 1.000000 1 R . .
C10 C -0.00577(18) 0.32722(16) 0.49007(16) 0.0390(5) Uani 1.000000 1 . . .


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 2.4210(13) 2 ?
Cu1 O1 2.4210(13) . ?
Cu1 N1 1.9881(15) . ?
Cu1 N1 1.9881(15) 2 ?
Cu1 N3 2.0175(14) . ?
Cu1 N3 2.0175(14) 2 ?
S1 O1 1.4413(13) . ?
S1 O2 1.4289(16) . ?
S1 O3 1.4441(14) . ?
S1 C10 1.826(2) . ?
N1 N2 1.345(2) . ?
N1 C1 1.333(2) . ?
N2 H2 0.8800 . ?
N2 C3 1.335(2) . ?
N3 C4 1.328(2) . ?
N3 C8 1.347(2) . ?
F1 C10 1.325(2) . ?
F2 C10 1.321(2) . ?
F3 C10 1.317(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.395(3) . ?
C2 H2a 0.9500 . ?
C2 C3 1.353(3) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.401(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.357(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.393(4) . ?
C7 C8 1.409(2) . ?
C7 C9 1.427(3) . ?
C8 C8 1.422(4) 2 ?
C9 C9 1.337(5) 2 ?
C9 H9 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 178.94(6) 2 . ?
N1 Cu1 O1 92.87(5) . 2 ?
N1 Cu1 O1 92.87(5) 2 . ?
N1 Cu1 O1 86.37(5) . . ?
N1 Cu1 O1 86.37(5) 2 2 ?
N1 Cu1 N1 88.90(9) 2 . ?
N3 Cu1 O1 95.18(5) 2 . ?
N3 Cu1 O1 85.63(5) 2 2 ?
N3 Cu1 O1 85.63(5) . . ?
N3 Cu1 O1 95.18(5) . 2 ?
N3 Cu1 N1 94.63(6) . . ?
N3 Cu1 N1 94.63(6) 2 2 ?
N3 Cu1 N1 176.07(6) . 2 ?
N3 Cu1 N1 176.07(6) 2 . ?
N3 Cu1 N3 81.91(8) 2 . ?
O2 S1 O1 115.20(9) . . ?
O3 S1 O1 113.62(9) . . ?
O3 S1 O2 116.15(9) . . ?
C10 S1 O1 102.92(9) . . ?
C10 S1 O2 103.45(10) . . ?
C10 S1 O3 103.03(9) . . ?
S1 O1 Cu1 147.85(9) . . ?
N2 N1 Cu1 121.09(11) . . ?
C1 N1 Cu1 132.88(13) . . ?
C1 N1 N2 105.74(15) . . ?
H2 N2 N1 124.38(9) . . ?
C3 N2 N1 111.24(16) . . ?
C3 N2 H2 124.38(12) . . ?
C4 N3 Cu1 129.33(14) . . ?
C8 N3 Cu1 112.07(12) . . ?
C8 N3 C4 118.59(16) . . ?
H1 C1 N1 125.15(11) . . ?
C2 C1 N1 109.71(18) . . ?
C2 C1 H1 125.15(12) . . ?
H2a C2 C1 127.14(12) . . ?
C3 C2 C1 105.72(18) . . ?
C3 C2 H2a 127.14(12) . . ?
C2 C3 N2 107.58(18) . . ?
H3 C3 N2 126.21(12) . . ?
H3 C3 C2 126.21(12) . . ?
H4 C4 N3 118.93(12) . . ?
C5 C4 N3 122.1(2) . . ?
C5 C4 H4 118.93(16) . . ?
H5 C5 C4 120.43(16) . . ?
C6 C5 C4 119.1(2) . . ?
C6 C5 H5 120.43(14) . . ?
H6 C6 C5 119.74(14) . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 119.74(13) . . ?
C8 C7 C6 116.8(2) . . ?
C9 C7 C6 125.2(2) . . ?
C9 C7 C8 118.1(2) . . ?
C7 C8 N3 122.84(18) . . ?
C8 C8 N3 116.98(10) 2 . ?
C8 C8 C7 120.18(13) 2 . ?
C9 C9 C7 121.73(13) 2 . ?
H9 C9 C7 119.14(13) . . ?
F1 C10 S1 110.40(14) . . ?
F2 C10 S1 111.48(14) . . ?
F2 C10 F1 106.53(18) . . ?
F3 C10 S1 111.59(15) . . ?
F3 C10 F1 108.81(19) . . ?
F3 C10 F2 107.85(18) . . ?

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 S1 O2 29.44(17) . . . . ?
Cu1 O1 S1 O2 29.44(17) 2 . . . ?
Cu1 O1 S1 O3 166.95(14) . . . . ?
Cu1 O1 S1 O3 166.95(14) 2 . . . ?
Cu1 O1 S1 C10 -82.38(16) 2 . . . ?
Cu1 O1 S1 C10 -82.38(16) . . . . ?
Cu1 N1 N2 C3 174.76(16) 2 . . . ?
Cu1 N1 N2 C3 174.76(16) . . . . ?
Cu1 N1 C1 C2 -174.0(2) 2 . . . ?
Cu1 N1 C1 C2 -174.0(2) . . . . ?
Cu1 N3 C4 C5 -179.25(19) . . . . ?
Cu1 N3 C4 C5 -179.25(19) 2 . . . ?
Cu1 N3 C8 C7 179.85(11) 2 . . . ?
Cu1 N3 C8 C7 179.85(11) . . . . ?
Cu1 N3 C8 C8 -0.22(13) . . . 2 ?
Cu1 N3 C8 C8 -0.22(13) . 2 2 . ?
N1 N2 C3 C2 0.08(19) . . . . ?
N1 C1 C2 C3 0.3(2) . . . . ?
N2 C3 C2 C1 -0.3(2) . . . . ?
N3 C4 C5 C6 -0.1(3) . . . . ?
N3 C8 C7 C6 -0.6(2) . . . . ?
N3 C8 C7 C9 179.58(18) . . . . ?
N3 C8 C8 N3 0.31(13) . . 2 2 ?
N3 C8 C8 C7 -179.76(18) . . 2 2 ?
C4 C5 C6 C7 0.7(3) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C5 C6 C7 C9 179.5(2) . . . . ?
C6 C7 C8 C8 179.5(2) . . . 2 ?
C6 C7 C9 C9 -179.1(3) . . . 2 ?
C7 C8 C8 C7 0.17(14) . . 2 2 ?
C7 C9 C9 C7 -1.0(2) . . 2 2 ?


_olex2_submission_special_instructions 'No special instructions were received'
