# 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_namiko66
_database_code_depnum_ccdc_archive 'CCDC 1871755'
loop_
_audit_author_name
_audit_author_address
'Nam1k ?zdemir'
;Ondokuz May1s University
Turkey
;
_audit_update_record             
;
2018-10-30 deposited with the CCDC.	2020-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 Cu N5 O S, H2 O'
_chemical_formula_sum            'C11 H17 Cu N5 O2 S'
_chemical_formula_weight         346.89

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.2697(7)
_cell_length_b                   10.9408(8)
_cell_length_c                   12.1483(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.229(5)
_cell_angle_gamma                90
_cell_volume                     1422.71(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    13266
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      29.11

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_F_000             716
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.680
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.690
_shelx_estimated_absorpt_T_min   0.393
_shelx_estimated_absorpt_T_max   0.877
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.4561
_exptl_absorpt_correction_T_max  0.8895
_exptl_absorpt_process_details   'X-RED32 (Stoe & Cie, 2002)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_collimation    '0.8 mm diameter, multiple pinhole'
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method, ω scan'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            10391
_diffrn_reflns_av_unetI/netI     0.0844
_diffrn_reflns_av_R_equivalents  0.1020
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.565
_diffrn_reflns_theta_max         28.682
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3644
_reflns_number_gt                2374
_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       'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement       X-AREA
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
'WinGX (Farrugia, 2012) and PLATON (Spek, 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)+(0.0550P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3644
_refine_ls_number_parameters     206
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_restrained_S_all      0.941
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.53310(4) 0.22336(3) 0.49299(4) 0.04095(14) Uani 1 1 d . . . . .
S1 S 0.34329(9) 0.64991(8) 0.24513(10) 0.0543(3) Uani 1 1 d . . . . .
O1 O 0.4102(2) 0.1544(2) 0.5557(2) 0.0464(6) Uani 1 1 d . . . . .
O2 O 0.4844(4) 0.0505(4) 0.2989(4) 0.0969(13) Uani 1 1 d D . . . .
H2A H 0.419(4) 0.043(5) 0.241(4) 0.13(3) Uiso 1 1 d D . . . .
H2B H 0.518(6) -0.020(3) 0.315(6) 0.15(3) Uiso 1 1 d D . . . .
N1 N 0.2705(3) 0.4903(2) 0.3787(3) 0.0437(7) Uani 1 1 d . . . . .
N2 N 0.4528(3) 0.4403(2) 0.3498(3) 0.0435(7) Uani 1 1 d . . . . .
N3 N 0.4235(3) 0.3543(2) 0.4216(3) 0.0411(6) Uani 1 1 d . . . . .
N4 N 0.6719(3) 0.2954(3) 0.4434(4) 0.0463(7) Uani 1 1 d . . . . .
H4A H 0.641(4) 0.318(4) 0.379(4) 0.069(15) Uiso 1 1 d . . . . .
H4B H 0.706(5) 0.353(5) 0.489(5) 0.085(17) Uiso 1 1 d . . . . .
N5 N 0.6594(3) 0.0926(3) 0.5623(4) 0.0499(8) Uani 1 1 d . . . . .
H5A H 0.670(4) 0.083(5) 0.635(5) 0.075(16) Uiso 1 1 d . . . . .
H5B H 0.629(5) 0.031(5) 0.526(5) 0.10(2) Uiso 1 1 d . . . . .
C1 C 0.3064(3) 0.2058(3) 0.5625(3) 0.0426(8) Uani 1 1 d . . . . .
C2 C 0.2391(4) 0.1469(4) 0.6262(3) 0.0522(9) Uani 1 1 d . . . . .
H2 H 0.268079 0.072142 0.660699 0.063 Uiso 1 1 calc R U . . .
C3 C 0.1321(4) 0.1948(4) 0.6398(4) 0.0615(11) Uani 1 1 d . . . . .
H3 H 0.088960 0.151703 0.681175 0.074 Uiso 1 1 calc R U . . .
C4 C 0.0885(4) 0.3069(4) 0.5921(4) 0.0634(11) Uani 1 1 d . . . . .
H4 H 0.017913 0.341221 0.603876 0.076 Uiso 1 1 calc R U . . .
C5 C 0.1502(3) 0.3672(4) 0.5273(4) 0.0553(10) Uani 1 1 d . . . . .
H5 H 0.119775 0.442061 0.494129 0.066 Uiso 1 1 calc R U . . .
C6 C 0.2577(3) 0.3187(3) 0.5098(3) 0.0405(7) Uani 1 1 d . . . . .
C7 C 0.3167(3) 0.3868(3) 0.4371(3) 0.0393(7) Uani 1 1 d . . . . .
C8 C 0.3595(3) 0.5173(3) 0.3292(3) 0.0408(7) Uani 1 1 d . . . . .
C9 C 0.4852(4) 0.6465(4) 0.2072(4) 0.0587(10) Uani 1 1 d . . . . .
H9A H 0.555264 0.637225 0.276085 0.088 Uiso 1 1 calc R U . . .
H9B H 0.493418 0.721524 0.169148 0.088 Uiso 1 1 calc R U . . .
H9C H 0.482641 0.579065 0.155943 0.088 Uiso 1 1 calc R U . . .
C10 C 0.7638(3) 0.1997(4) 0.4450(4) 0.0524(9) Uani 1 1 d . . . . .
H10A H 0.841900 0.236103 0.443675 0.063 Uiso 1 1 calc R U . . .
H10B H 0.733044 0.146959 0.377906 0.063 Uiso 1 1 calc R U . . .
C11 C 0.7831(3) 0.1286(4) 0.5535(4) 0.0547(10) Uani 1 1 d . . . . .
H11A H 0.832546 0.056311 0.552552 0.066 Uiso 1 1 calc R U . . .
H11B H 0.827554 0.177925 0.619971 0.066 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 1.913(3) . ?
Cu1 O1 1.931(3) . ?
Cu1 N4 2.005(3) . ?
Cu1 N5 2.008(3) . ?
S1 C8 1.751(3) . ?
S1 C9 1.798(5) . ?
O1 C1 1.324(4) . ?
O2 H2A 0.848(19) . ?
O2 H2B 0.855(19) . ?
N1 C7 1.352(4) . ?
N1 C8 1.354(5) . ?
N2 C8 1.309(4) . ?
N2 N3 1.391(4) . ?
N3 C7 1.325(4) . ?
N4 C10 1.469(5) . ?
N4 H4A 0.78(5) . ?
N4 H4B 0.85(5) . ?
N5 C11 1.484(5) . ?
N5 H5A 0.86(5) . ?
N5 H5B 0.82(6) . ?
C1 C2 1.399(5) . ?
C1 C6 1.419(5) . ?
C2 C3 1.371(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.464(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.488(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

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 O1 91.75(11) . . ?
N3 Cu1 N4 91.32(13) . . ?
O1 Cu1 N4 174.53(14) . . ?
N3 Cu1 N5 174.92(13) . . ?
O1 Cu1 N5 93.33(12) . . ?
N4 Cu1 N5 83.61(13) . . ?
C8 S1 C9 101.17(18) . . ?
C1 O1 Cu1 128.0(2) . . ?
H2A O2 H2B 108(3) . . ?
C7 N1 C8 101.5(3) . . ?
C8 N2 N3 102.8(3) . . ?
C7 N3 N2 108.2(3) . . ?
C7 N3 Cu1 128.5(3) . . ?
N2 N3 Cu1 123.0(2) . . ?
C10 N4 Cu1 109.3(2) . . ?
C10 N4 H4A 109(4) . . ?
Cu1 N4 H4A 106(4) . . ?
C10 N4 H4B 110(3) . . ?
Cu1 N4 H4B 110(4) . . ?
H4A N4 H4B 112(5) . . ?
C11 N5 Cu1 109.8(2) . . ?
C11 N5 H5A 106(3) . . ?
Cu1 N5 H5A 112(3) . . ?
C11 N5 H5B 115(4) . . ?
Cu1 N5 H5B 104(4) . . ?
H5A N5 H5B 110(5) . . ?
O1 C1 C2 118.7(3) . . ?
O1 C1 C6 124.5(3) . . ?
C2 C1 C6 116.8(3) . . ?
C3 C2 C1 122.6(4) . . ?
C3 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
C2 C3 C4 120.1(4) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.3(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.6(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 119.5(4) . . ?
C5 C6 C7 118.5(3) . . ?
C1 C6 C7 122.0(3) . . ?
N3 C7 N1 111.6(3) . . ?
N3 C7 C6 123.6(3) . . ?
N1 C7 C6 124.8(3) . . ?
N2 C8 N1 116.0(3) . . ?
N2 C8 S1 125.2(3) . . ?
N1 C8 S1 118.9(2) . . ?
S1 C9 H9A 109.5 . . ?
S1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
S1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C10 C11 106.9(3) . . ?
N4 C10 H10A 110.3 . . ?
C11 C10 H10A 110.3 . . ?
N4 C10 H10B 110.3 . . ?
C11 C10 H10B 110.3 . . ?
H10A C10 H10B 108.6 . . ?
N5 C11 C10 108.9(3) . . ?
N5 C11 H11A 109.9 . . ?
C10 C11 H11A 109.9 . . ?
N5 C11 H11B 109.9 . . ?
C10 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N2 N3 C7 0.1(3) . . . . ?
C8 N2 N3 Cu1 -174.6(2) . . . . ?
Cu1 O1 C1 C2 -170.9(2) . . . . ?
Cu1 O1 C1 C6 8.7(5) . . . . ?
O1 C1 C2 C3 178.6(3) . . . . ?
C6 C1 C2 C3 -1.0(5) . . . . ?
C1 C2 C3 C4 -1.6(6) . . . . ?
C2 C3 C4 C5 2.7(6) . . . . ?
C3 C4 C5 C6 -1.1(6) . . . . ?
C4 C5 C6 C1 -1.5(6) . . . . ?
C4 C5 C6 C7 178.5(3) . . . . ?
O1 C1 C6 C5 -177.1(3) . . . . ?
C2 C1 C6 C5 2.5(5) . . . . ?
O1 C1 C6 C7 2.9(5) . . . . ?
C2 C1 C6 C7 -177.5(3) . . . . ?
N2 N3 C7 N1 0.6(4) . . . . ?
Cu1 N3 C7 N1 174.9(2) . . . . ?
N2 N3 C7 C6 -178.9(3) . . . . ?
Cu1 N3 C7 C6 -4.6(5) . . . . ?
C8 N1 C7 N3 -1.0(4) . . . . ?
C8 N1 C7 C6 178.4(3) . . . . ?
C5 C6 C7 N3 174.9(3) . . . . ?
C1 C6 C7 N3 -5.1(5) . . . . ?
C5 C6 C7 N1 -4.5(5) . . . . ?
C1 C6 C7 N1 175.5(3) . . . . ?
N3 N2 C8 N1 -0.8(4) . . . . ?
N3 N2 C8 S1 178.7(2) . . . . ?
C7 N1 C8 N2 1.2(4) . . . . ?
C7 N1 C8 S1 -178.4(2) . . . . ?
C9 S1 C8 N2 -2.1(3) . . . . ?
C9 S1 C8 N1 177.4(3) . . . . ?
Cu1 N4 C10 C11 -43.3(4) . . . . ?
Cu1 N5 C11 C10 -33.6(4) . . . . ?
N4 C10 C11 N5 50.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4A N2 0.78(5) 2.44(5) 2.854(4) 114(4) . yes
N5 H5B O1 0.82(6) 2.24(6) 3.044(5) 167(5) 3_656 yes
O2 H2A N1 0.848(19) 2.25(3) 3.076(5) 164(7) 2_545 yes
N4 H4B N1 0.85(5) 2.31(6) 3.117(5) 159(5) 3_666 yes
O2 H2B O1 0.855(19) 2.12(5) 2.871(5) 147(7) 3_656 yes
N5 H5A O2 0.86(5) 2.59(5) 3.103(5) 120(4) 3_656 yes

_refine_diff_density_max         0.627
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_namiko5
_database_code_depnum_ccdc_archive 'CCDC 1946926'
loop_
_audit_author_name
_audit_author_address
'Namik Ozdemir'
;Ondokuz Mayis University
Turkey
;
_audit_update_record             
;
2019-08-13 deposited with the CCDC.	2020-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H28 Cu2 N4 O4'
_chemical_formula_sum            'C32 H28 Cu2 N4 O4'
_chemical_formula_weight         659.66

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   26.6117(12)
_cell_length_b                   6.9913(2)
_cell_length_c                   14.7280(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.479(4)
_cell_angle_gamma                90
_cell_volume                     2716.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    19438
_cell_measurement_theta_min      1.39
_cell_measurement_theta_max      27.63

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_F_000             1352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.613
_shelx_estimated_absorpt_T_min   0.626
_shelx_estimated_absorpt_T_max   0.909
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.6092
_exptl_absorpt_correction_T_max  0.9023
_exptl_absorpt_process_details   'X-RED32 (Stoe & Cie, 2002)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_collimation    '0.5 mm diameter, multiple pinhole'
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            13671
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.544
_diffrn_reflns_theta_max         27.120
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2997
_reflns_number_gt                2295
_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       'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement       X-AREA
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_structure_solution    'SIR-2019 (Burla et al., 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 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)+(0.0489P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2997
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0824
_refine_ls_wR_factor_gt          0.0778
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_restrained_S_all      0.949
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.26712(2) 0.70575(4) 0.40207(2) 0.03588(11) Uani 1 1 d . . . . .
O1 O 0.21542(6) 0.8766(2) 0.43747(10) 0.0380(4) Uani 1 1 d . . . . .
O2 O 0.31565(7) 0.9080(3) 0.41094(12) 0.0455(4) Uani 1 1 d . . . . .
N1 N 0.21731(9) 0.5030(3) 0.37263(13) 0.0416(5) Uani 1 1 d . . . . .
N2 N 0.31187(8) 0.5313(3) 0.34666(13) 0.0401(5) Uani 1 1 d . . . . .
C1 C 0.16664(9) 0.8631(4) 0.40973(15) 0.0397(5) Uani 1 1 d . . . . .
C2 C 0.13569(11) 1.0215(4) 0.42234(18) 0.0499(7) Uani 1 1 d . . . . .
H2 H 0.150459 1.131595 0.449448 0.060 Uiso 1 1 calc R U . . .
C3 C 0.08401(12) 1.0182(5) 0.3956(2) 0.0640(8) Uani 1 1 d . . . . .
H3 H 0.064564 1.124936 0.405379 0.077 Uiso 1 1 calc R U . . .
C4 C 0.06095(12) 0.8574(6) 0.3545(2) 0.0691(9) Uani 1 1 d . . . . .
H4 H 0.026185 0.855988 0.335879 0.083 Uiso 1 1 calc R U . . .
C5 C 0.08979(11) 0.7009(5) 0.3414(2) 0.0597(8) Uani 1 1 d . . . . .
H5 H 0.074093 0.592889 0.313853 0.072 Uiso 1 1 calc R U . . .
C6 C 0.14246(10) 0.6976(4) 0.36823(16) 0.0443(6) Uani 1 1 d . . . . .
C7 C 0.16947(11) 0.5245(4) 0.35565(16) 0.0463(6) Uani 1 1 d . . . . .
H7 H 0.150514 0.418932 0.333216 0.056 Uiso 1 1 calc R U . . .
C8 C 0.24171(12) 0.3193(4) 0.36005(18) 0.0510(7) Uani 1 1 d . . . . .
H8A H 0.218008 0.232644 0.325472 0.061 Uiso 1 1 calc R U . . .
H8B H 0.253230 0.261558 0.418969 0.061 Uiso 1 1 calc R U . . .
C9 C 0.28621(12) 0.3578(4) 0.30854(18) 0.0506(7) Uani 1 1 d . . . . .
H9A H 0.309453 0.250338 0.315108 0.061 Uiso 1 1 calc R U . . .
H9B H 0.274524 0.375574 0.243921 0.061 Uiso 1 1 calc R U . . .
C10 C 0.35793(11) 0.5624(4) 0.33566(16) 0.0462(6) Uani 1 1 d . . . . .
H10 H 0.374775 0.465965 0.308269 0.055 Uiso 1 1 calc R U . . .
C11 C 0.38584(11) 0.7326(4) 0.36183(17) 0.0457(6) Uani 1 1 d . . . . .
C12 C 0.43705(12) 0.7390(5) 0.3494(2) 0.0617(8) Uani 1 1 d . . . . .
H12 H 0.451436 0.632929 0.324687 0.074 Uiso 1 1 calc R U . . .
C13 C 0.46672(12) 0.8963(6) 0.3724(2) 0.0691(9) Uani 1 1 d . . . . .
H13 H 0.500649 0.897353 0.363276 0.083 Uiso 1 1 calc R U . . .
C14 C 0.44519(12) 1.0535(5) 0.4094(2) 0.0627(8) Uani 1 1 d . . . . .
H14 H 0.465168 1.159883 0.426594 0.075 Uiso 1 1 calc R U . . .
C15 C 0.39499(11) 1.0551(4) 0.42111(19) 0.0529(7) Uani 1 1 d . . . . .
H15 H 0.381472 1.164301 0.444655 0.063 Uiso 1 1 calc R U . . .
C16 C 0.36313(10) 0.8959(4) 0.39851(15) 0.0411(6) 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 O2 1.9081(18) . ?
Cu1 O1 1.9435(16) . ?
Cu1 N1 1.950(2) . ?
Cu1 N2 1.956(2) . ?
Cu1 O1 2.4178(15) 7_566 ?
O1 C1 1.313(3) . ?
O2 C16 1.303(3) . ?
N1 C7 1.274(3) . ?
N1 C8 1.462(3) . ?
N2 C10 1.276(3) . ?
N2 C9 1.468(3) . ?
C1 C2 1.407(4) . ?
C1 C6 1.423(4) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.406(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.432(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.511(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.429(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.399(4) . ?
C11 C16 1.431(4) . ?
C12 C13 1.370(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.413(4) . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O1 91.31(7) . . ?
O2 Cu1 N1 171.15(8) . . ?
O1 Cu1 N1 91.26(8) . . ?
O2 Cu1 N2 92.69(8) . . ?
O1 Cu1 N2 170.36(7) . . ?
N1 Cu1 N2 83.52(9) . . ?
O2 Cu1 O1 93.86(7) . 7_566 ?
O1 Cu1 O1 86.37(6) . 7_566 ?
N1 Cu1 O1 94.75(7) . 7_566 ?
N2 Cu1 O1 102.09(7) . 7_566 ?
C1 O1 Cu1 125.35(16) . . ?
C1 O1 Cu1 110.10(13) . 7_566 ?
Cu1 O1 Cu1 93.62(6) . 7_566 ?
C16 O2 Cu1 127.05(17) . . ?
C7 N1 C8 121.9(2) . . ?
C7 N1 Cu1 126.21(19) . . ?
C8 N1 Cu1 111.50(18) . . ?
C10 N2 C9 119.9(2) . . ?
C10 N2 Cu1 126.47(18) . . ?
C9 N2 Cu1 113.37(17) . . ?
O1 C1 C2 118.4(2) . . ?
O1 C1 C6 124.4(2) . . ?
C2 C1 C6 117.2(2) . . ?
C3 C2 C1 121.8(3) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 122.1(3) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 C7 118.5(3) . . ?
C1 C6 C7 122.4(2) . . ?
N1 C7 C6 125.4(2) . . ?
N1 C7 H7 117.3 . . ?
C6 C7 H7 117.3 . . ?
N1 C8 C9 107.3(2) . . ?
N1 C8 H8A 110.3 . . ?
C9 C8 H8A 110.3 . . ?
N1 C8 H8B 110.3 . . ?
C9 C8 H8B 110.3 . . ?
H8A C8 H8B 108.5 . . ?
N2 C9 C8 108.1(2) . . ?
N2 C9 H9A 110.1 . . ?
C8 C9 H9A 110.1 . . ?
N2 C9 H9B 110.1 . . ?
C8 C9 H9B 110.1 . . ?
H9A C9 H9B 108.4 . . ?
N2 C10 C11 125.6(2) . . ?
N2 C10 H10 117.2 . . ?
C11 C10 H10 117.2 . . ?
C12 C11 C10 118.2(3) . . ?
C12 C11 C16 119.4(3) . . ?
C10 C11 C16 122.4(3) . . ?
C13 C12 C11 122.2(3) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C12 C13 C14 118.7(3) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
C15 C14 C13 121.1(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 122.0(3) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
O2 C16 C15 118.6(3) . . ?
O2 C16 C11 124.8(2) . . ?
C15 C16 C11 116.6(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 C2 -164.41(16) . . . . ?
Cu1 O1 C1 C2 85.6(2) 7_566 . . . ?
Cu1 O1 C1 C6 16.3(3) . . . . ?
Cu1 O1 C1 C6 -93.7(2) 7_566 . . . ?
O1 C1 C2 C3 -179.5(2) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C4 C5 C6 C1 -0.5(4) . . . . ?
C4 C5 C6 C7 177.3(3) . . . . ?
O1 C1 C6 C5 180.0(2) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
O1 C1 C6 C7 2.3(4) . . . . ?
C2 C1 C6 C7 -177.0(2) . . . . ?
C8 N1 C7 C6 178.4(2) . . . . ?
Cu1 N1 C7 C6 -9.9(4) . . . . ?
C5 C6 C7 N1 176.5(2) . . . . ?
C1 C6 C7 N1 -5.8(4) . . . . ?
C7 N1 C8 C9 132.9(3) . . . . ?
Cu1 N1 C8 C9 -40.0(2) . . . . ?
C10 N2 C9 C8 158.7(2) . . . . ?
Cu1 N2 C9 C8 -26.4(3) . . . . ?
N1 C8 C9 N2 41.9(3) . . . . ?
C9 N2 C10 C11 174.0(2) . . . . ?
Cu1 N2 C10 C11 -0.2(4) . . . . ?
N2 C10 C11 C12 176.5(3) . . . . ?
N2 C10 C11 C16 -4.5(4) . . . . ?
C10 C11 C12 C13 179.9(3) . . . . ?
C16 C11 C12 C13 0.9(5) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
C12 C13 C14 C15 -1.5(5) . . . . ?
C13 C14 C15 C16 1.7(5) . . . . ?
Cu1 O2 C16 C15 -170.85(17) . . . . ?
Cu1 O2 C16 C11 10.2(3) . . . . ?
C14 C15 C16 O2 -179.6(3) . . . . ?
C14 C15 C16 C11 -0.5(4) . . . . ?
C12 C11 C16 O2 178.2(3) . . . . ?
C10 C11 C16 O2 -0.7(4) . . . . ?
C12 C11 C16 C15 -0.7(4) . . . . ?
C10 C11 C16 C15 -179.7(2) . . . . ?

_refine_diff_density_max         0.620
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.063

