# 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 2024

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2263468'
loop_
_audit_author_name
_audit_author_address
'M. Sankaralingam'
;National Institute of Technology Calicut
India
;
_audit_update_record             
;
2023-05-16 deposited with the CCDC.	2024-05-29 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         ?
_chemical_formula_sum            'C32 H34 Cu2 N10 O2'
_chemical_formula_weight         717.77

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

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

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

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

_cell_length_a                   9.489(2)
_cell_length_b                   9.759(3)
_cell_length_c                   10.043(3)
_cell_angle_alpha                63.432(9)
_cell_angle_beta                 89.480(9)
_cell_angle_gamma                71.598(9)
_cell_volume                     779.6(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    23617
_cell_measurement_theta_min      2.290
_cell_measurement_theta_max      28.543

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_F_000             370
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.052
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.039
_exptl_absorpt_coefficient_mu    1.412
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23617
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.290
_diffrn_reflns_theta_max         28.543
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3924
_reflns_number_gt                3097
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²+0.2176P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3924
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0937
_refine_ls_wR_factor_gt          0.0861
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.06528(3) 0.42961(3) 0.17802(3) 0.04060(11) Uani 1 1 d . . . . .
O1 O -0.07012(19) 0.6135(2) 0.18982(19) 0.0505(4) Uani 1 1 d . . . . .
N2 N 0.2182(2) 0.2404(2) 0.1580(2) 0.0442(4) Uani 1 1 d . . . . .
N1 N 0.2317(2) 0.4079(2) 0.3037(2) 0.0429(4) Uani 1 1 d . . . . .
N4 N -0.2013(2) 0.3711(2) 0.1523(2) 0.0449(4) Uani 1 1 d . . . . .
N3 N -0.0993(2) 0.3966(3) 0.0887(2) 0.0507(5) Uani 1 1 d . . . . .
C11 C 0.2791(3) -0.0502(3) 0.2077(2) 0.0419(5) Uani 1 1 d . . . . .
C10 C 0.2068(3) 0.0772(3) 0.2555(3) 0.0483(6) Uani 1 1 d . . . . .
N5 N -0.3004(3) 0.3430(4) 0.2097(3) 0.0782(8) Uani 1 1 d . . . . .
C8 C 0.3718(3) 0.2785(4) 0.3215(3) 0.0539(6) Uani 1 1 d . . . . .
C7 C 0.2236(3) 0.4882(3) 0.3774(3) 0.0479(6) Uani 1 1 d . . . . .
C16 C 0.2003(3) -0.0608(3) 0.1014(3) 0.0556(6) Uani 1 1 d . . . . .
C9 C 0.3656(3) 0.2513(3) 0.1843(3) 0.0527(6) Uani 1 1 d . . . . .
C5 C 0.0938(3) 0.6163(3) 0.3707(3) 0.0467(6) Uani 1 1 d . . . . .
C6 C -0.0449(3) 0.6748(3) 0.2761(3) 0.0470(6) Uani 1 1 d . . . . .
C12 C 0.4234(4) -0.1614(4) 0.2674(4) 0.0734(9) Uani 1 1 d . . . . .
C4 C 0.1073(4) 0.6887(4) 0.4620(3) 0.0615(8) Uani 1 1 d . . . . .
C1 C -0.1598(4) 0.8075(3) 0.2763(3) 0.0604(7) Uani 1 1 d . . . . .
C14 C 0.4032(4) -0.2868(4) 0.1165(4) 0.0644(8) Uani 1 1 d . . . . .
C15 C 0.2613(4) -0.1782(4) 0.0557(3) 0.0659(8) Uani 1 1 d . . . . .
C3 C -0.0080(5) 0.8168(4) 0.4587(4) 0.0746(10) Uani 1 1 d . . . . .
C2 C -0.1393(5) 0.8767(4) 0.3649(4) 0.0731(10) Uani 1 1 d . . . . .
C13 C 0.4835(4) -0.2788(4) 0.2203(5) 0.0846(11) Uani 1 1 d . . . . .
H9 H 0.444(3) 0.158(3) 0.194(3) 0.050(7) Uiso 1 1 d . . . . .
H11 H 0.243(3) 0.045(3) 0.356(3) 0.051(7) Uiso 1 1 d . . . . .
H7 H 0.380(3) 0.179(3) 0.413(3) 0.057(8) Uiso 1 1 d . . . . .
H12 H 0.105(3) 0.089(3) 0.258(3) 0.064(8) Uiso 1 1 d . . . . .
H6 H 0.454(3) 0.305(3) 0.328(3) 0.049(7) Uiso 1 1 d . . . . .
H8 H 0.376(2) 0.343(3) 0.092(3) 0.045(6) Uiso 1 1 d . . . . .
H5 H 0.311(3) 0.465(3) 0.439(3) 0.040(6) Uiso 1 1 d . . . . .
H1 H -0.242(3) 0.844(3) 0.218(3) 0.036(7) Uiso 1 1 d . . . . .
H17 H 0.118(3) 0.014(4) 0.057(3) 0.073(10) Uiso 1 1 d . . . . .
H2 H -0.216(3) 0.958(3) 0.361(3) 0.057(8) Uiso 1 1 d . . . . .
H3 H 0.012(4) 0.858(4) 0.519(4) 0.086(11) Uiso 1 1 d . . . . .
H16 H 0.207(4) -0.185(5) -0.017(4) 0.114(13) Uiso 1 1 d . . . . .
H15 H 0.446(4) -0.363(4) 0.085(4) 0.095(11) Uiso 1 1 d . . . . .
H13 H 0.466(4) -0.161(4) 0.336(4) 0.091(12) Uiso 1 1 d . . . . .
H14 H 0.566(4) -0.333(5) 0.248(5) 0.105(14) Uiso 1 1 d . . . . .
H4 H 0.193(3) 0.658(4) 0.515(3) 0.065(10) Uiso 1 1 d . . . . .
H10 H 0.201(3) 0.264(3) 0.070(3) 0.042(7) Uiso 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 1.9020(17) . ?
Cu1 N1 1.9281(19) . ?
Cu1 N3 1.987(2) . ?
Cu1 N2 2.047(2) . ?
O1 C6 1.313(3) . ?
N2 C9 1.471(3) . ?
N2 C10 1.489(3) . ?
N2 H10 0.82(3) . ?
N1 C7 1.284(3) . ?
N1 C8 1.462(3) . ?
N4 N5 1.142(3) . ?
N4 N3 1.186(3) . ?
C11 C16 1.367(4) . ?
C11 C12 1.381(4) . ?
C11 C10 1.496(3) . ?
C10 H11 0.94(3) . ?
C10 H12 0.94(3) . ?
C8 C9 1.520(4) . ?
C8 H7 0.98(3) . ?
C8 H6 0.91(3) . ?
C7 C5 1.427(4) . ?
C7 H5 0.94(2) . ?
C16 C15 1.381(4) . ?
C16 H17 0.83(3) . ?
C9 H9 0.94(3) . ?
C9 H8 0.99(2) . ?
C5 C4 1.413(3) . ?
C5 C6 1.422(4) . ?
C6 C1 1.406(4) . ?
C12 C13 1.389(5) . ?
C12 H13 0.81(4) . ?
C4 C3 1.364(5) . ?
C4 H4 0.86(3) . ?
C1 C2 1.382(4) . ?
C1 H1 0.85(2) . ?
C14 C13 1.341(5) . ?
C14 C15 1.358(5) . ?
C14 H15 0.92(4) . ?
C15 H16 0.93(4) . ?
C3 C2 1.360(5) . ?
C3 H3 0.91(3) . ?
C2 H2 0.88(3) . ?
C13 H14 0.76(4) . ?

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 N1 94.54(8) . . ?
O1 Cu1 N3 92.44(8) . . ?
N1 Cu1 N3 165.79(8) . . ?
O1 Cu1 N2 176.55(7) . . ?
N1 Cu1 N2 84.16(9) . . ?
N3 Cu1 N2 89.53(9) . . ?
C6 O1 Cu1 126.32(16) . . ?
C9 N2 C10 114.2(2) . . ?
C9 N2 Cu1 105.16(15) . . ?
C10 N2 Cu1 114.61(15) . . ?
C9 N2 H10 108.0(17) . . ?
C10 N2 H10 109.6(18) . . ?
Cu1 N2 H10 104.7(18) . . ?
C7 N1 C8 120.3(2) . . ?
C7 N1 Cu1 125.13(18) . . ?
C8 N1 Cu1 114.34(16) . . ?
N5 N4 N3 176.8(3) . . ?
N4 N3 Cu1 121.95(17) . . ?
C16 C11 C12 117.3(2) . . ?
C16 C11 C10 119.6(2) . . ?
C12 C11 C10 123.0(2) . . ?
N2 C10 C11 114.9(2) . . ?
N2 C10 H11 108.2(16) . . ?
C11 C10 H11 112.9(16) . . ?
N2 C10 H12 108.9(17) . . ?
C11 C10 H12 108.3(18) . . ?
H11 C10 H12 103(2) . . ?
N1 C8 C9 107.4(2) . . ?
N1 C8 H7 109.2(16) . . ?
C9 C8 H7 110.6(16) . . ?
N1 C8 H6 112.1(16) . . ?
C9 C8 H6 109.4(16) . . ?
H7 C8 H6 108(2) . . ?
N1 C7 C5 125.8(2) . . ?
N1 C7 H5 118.1(15) . . ?
C5 C7 H5 116.1(15) . . ?
C11 C16 C15 121.7(3) . . ?
C11 C16 H17 117(2) . . ?
C15 C16 H17 121(2) . . ?
N2 C9 C8 108.4(2) . . ?
N2 C9 H9 111.0(15) . . ?
C8 C9 H9 112.7(15) . . ?
N2 C9 H8 107.4(13) . . ?
C8 C9 H8 112.2(14) . . ?
H9 C9 H8 105(2) . . ?
C4 C5 C6 119.3(3) . . ?
C4 C5 C7 117.2(3) . . ?
C6 C5 C7 123.5(2) . . ?
O1 C6 C1 119.2(3) . . ?
O1 C6 C5 124.1(2) . . ?
C1 C6 C5 116.7(2) . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 H13 117(3) . . ?
C13 C12 H13 122(3) . . ?
C3 C4 C5 121.7(3) . . ?
C3 C4 H4 119(2) . . ?
C5 C4 H4 119(2) . . ?
C2 C1 C6 121.6(3) . . ?
C2 C1 H1 121.7(17) . . ?
C6 C1 H1 116.7(17) . . ?
C13 C14 C15 119.7(3) . . ?
C13 C14 H15 119(2) . . ?
C15 C14 H15 121(2) . . ?
C14 C15 C16 119.9(3) . . ?
C14 C15 H16 119(2) . . ?
C16 C15 H16 121(2) . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 125(2) . . ?
C4 C3 H3 115(2) . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 121.7(19) . . ?
C1 C2 H2 116.9(19) . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H14 120(3) . . ?
C12 C13 H14 119(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
C9 N2 C10 C11 -77.9(3) . . . . ?
Cu1 N2 C10 C11 160.66(18) . . . . ?
C16 C11 C10 N2 -85.1(3) . . . . ?
C12 C11 C10 N2 95.7(3) . . . . ?
C7 N1 C8 C9 -159.7(2) . . . . ?
Cu1 N1 C8 C9 25.3(3) . . . . ?
C8 N1 C7 C5 -179.7(2) . . . . ?
Cu1 N1 C7 C5 -5.3(3) . . . . ?
C12 C11 C16 C15 0.4(4) . . . . ?
C10 C11 C16 C15 -178.8(3) . . . . ?
C10 N2 C9 C8 -80.9(3) . . . . ?
Cu1 N2 C9 C8 45.5(2) . . . . ?
N1 C8 C9 N2 -47.0(3) . . . . ?
N1 C7 C5 C4 179.4(2) . . . . ?
N1 C7 C5 C6 -1.6(4) . . . . ?
Cu1 O1 C6 C1 -177.27(17) . . . . ?
Cu1 O1 C6 C5 3.3(3) . . . . ?
C4 C5 C6 O1 -178.3(2) . . . . ?
C7 C5 C6 O1 2.7(3) . . . . ?
C4 C5 C6 C1 2.3(3) . . . . ?
C7 C5 C6 C1 -176.7(2) . . . . ?
C16 C11 C12 C13 -0.3(5) . . . . ?
C10 C11 C12 C13 178.9(3) . . . . ?
C6 C5 C4 C3 -2.0(4) . . . . ?
C7 C5 C4 C3 177.0(2) . . . . ?
O1 C6 C1 C2 180.0(2) . . . . ?
C5 C6 C1 C2 -0.6(4) . . . . ?
C13 C14 C15 C16 -0.4(5) . . . . ?
C11 C16 C15 C14 -0.1(5) . . . . ?
C5 C4 C3 C2 -0.1(4) . . . . ?
C4 C3 C2 C1 1.8(5) . . . . ?
C6 C1 C2 C3 -1.5(4) . . . . ?
C15 C14 C13 C12 0.5(6) . . . . ?
C11 C12 C13 C14 -0.1(6) . . . . ?

_refine_diff_density_max         0.325
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.066



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

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2263469'
loop_
_audit_author_name
_audit_author_address
'MUNIYANDI SANKARALINGAM'
;National Institute of Technology Calicut
India
;
_audit_update_record             
;
2023-05-16 deposited with the CCDC.	2024-05-29 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         ?
_chemical_formula_sum            'C17 H19 Cu N5 O'
_chemical_formula_weight         372.91

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      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

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

_cell_length_a                   13.7472(19)
_cell_length_b                   28.684(4)
_cell_length_c                   8.5539(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3373.1(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    26344
_cell_measurement_theta_min      2.595
_cell_measurement_theta_max      28.310

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_F_000             1544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.053
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.038
_exptl_absorpt_coefficient_mu    1.309
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26344
_diffrn_reflns_av_unetI/netI     0.1223
_diffrn_reflns_av_R_equivalents  0.1300
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.595
_diffrn_reflns_theta_max         28.310
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4156
_reflns_number_gt                2226
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+12.1511P] 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         4156
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1464
_refine_ls_R_factor_gt           0.0680
_refine_ls_wR_factor_ref         0.1638
_refine_ls_wR_factor_gt          0.1385
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.31250(5) 0.55143(2) 0.77207(8) 0.0362(2) Uani 1 1 d . . . . .
O1 O 0.2572(3) 0.51191(11) 0.9282(4) 0.0418(9) Uani 1 1 d . . . . .
N2 N 0.3774(3) 0.58996(13) 0.5994(5) 0.0325(10) Uani 1 1 d . . . . .
H003 H 0.334112 0.589737 0.508353 0.039 Uiso 1 1 calc R U . . .
N1 N 0.4371(3) 0.51932(14) 0.7822(5) 0.0337(10) Uani 1 1 d . . . . .
N4 N 0.1654(3) 0.59775(16) 0.6177(6) 0.0390(11) Uani 1 1 d . . . . .
N3 N 0.1835(3) 0.58065(16) 0.7421(6) 0.0449(12) Uani 1 1 d . . . . .
C1 C 0.2886(4) 0.47005(17) 0.9634(6) 0.0328(12) Uani 1 1 d . . . . .
N5 N 0.1457(4) 0.61350(19) 0.4970(7) 0.0576(14) Uani 1 1 d . . . . .
C7 C 0.4514(4) 0.47832(18) 0.8373(6) 0.0354(12) Uani 1 1 d . . . . .
H009 H 0.513162 0.465534 0.825320 0.042 Uiso 1 1 calc R U . . .
C6 C 0.3794(4) 0.45064(17) 0.9161(6) 0.0322(11) Uani 1 1 d . . . . .
C9 C 0.4684(4) 0.56457(17) 0.5557(6) 0.0381(13) Uani 1 1 d . . . . .
H00A H 0.513403 0.585787 0.505097 0.046 Uiso 1 1 calc R U . . .
H00B H 0.453248 0.539627 0.483071 0.046 Uiso 1 1 calc R U . . .
C8 C 0.5142(4) 0.54465(18) 0.7018(6) 0.0395(13) Uani 1 1 d . . . . .
H00C H 0.567225 0.523813 0.675031 0.047 Uiso 1 1 calc R U . . .
H00D H 0.539345 0.569428 0.767546 0.047 Uiso 1 1 calc R U . . .
C5 C 0.4018(4) 0.40393(18) 0.9525(7) 0.0390(13) Uani 1 1 d . . . . .
H00E H 0.460796 0.391655 0.918810 0.047 Uiso 1 1 calc R U . . .
C3 C 0.2524(4) 0.39613(18) 1.0877(7) 0.0433(14) Uani 1 1 d . . . . .
H00F H 0.210036 0.378404 1.148063 0.052 Uiso 1 1 calc R U . . .
C2 C 0.2276(4) 0.44096(18) 1.0524(7) 0.0404(14) Uani 1 1 d . . . . .
H00G H 0.168600 0.452647 1.088334 0.049 Uiso 1 1 calc R U . . .
C11 C 0.4250(5) 0.66973(18) 0.5073(7) 0.0450(15) Uani 1 1 d . . . . .
C4 C 0.3395(4) 0.37578(18) 1.0362(7) 0.0414(14) Uani 1 1 d . . . . .
C10 C 0.3954(4) 0.63971(17) 0.6432(7) 0.0440(15) Uani 1 1 d . . . . .
H00H H 0.446119 0.640800 0.721917 0.053 Uiso 1 1 calc R U . . .
H00I H 0.336640 0.652454 0.689322 0.053 Uiso 1 1 calc R U . . .
C12 C 0.5211(5) 0.6787(2) 0.4759(8) 0.0556(18) Uani 1 1 d . . . . .
H00J H 0.569002 0.666641 0.541088 0.067 Uiso 1 1 calc R U . . .
C17 C 0.3634(5) 0.32555(19) 1.0710(9) 0.064(2) Uani 1 1 d . . . . .
H00K H 0.324549 0.305626 1.005936 0.096 Uiso 1 1 calc R U . . .
H00L H 0.349710 0.319050 1.178928 0.096 Uiso 1 1 calc R U . . .
H00M H 0.431030 0.319985 1.050482 0.096 Uiso 1 1 calc R U . . .
C16 C 0.3541(6) 0.6883(2) 0.4105(9) 0.066(2) Uani 1 1 d . . . . .
H00N H 0.288569 0.683183 0.431039 0.079 Uiso 1 1 calc R U . . .
C13 C 0.5477(7) 0.7056(2) 0.3479(11) 0.079(2) Uani 1 1 d . . . . .
H00O H 0.612977 0.711483 0.327235 0.095 Uiso 1 1 calc R U . . .
C15 C 0.3823(8) 0.7146(3) 0.2831(10) 0.088(3) Uani 1 1 d . . . . .
H00P H 0.335078 0.726624 0.216419 0.105 Uiso 1 1 calc R U . . .
C14 C 0.4774(9) 0.7234(3) 0.2531(11) 0.097(3) Uani 1 1 d . . . . .
H00Q H 0.494702 0.741561 0.167509 0.116 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 O1 1.910(4) . ?
Cu1 N1 1.946(4) . ?
Cu1 N3 1.978(5) . ?
Cu1 N2 2.049(4) . ?
O1 C1 1.311(6) . ?
N2 C9 1.495(7) . ?
N2 C10 1.496(6) . ?
N2 H003 0.9800 . ?
N1 C7 1.282(6) . ?
N1 C8 1.458(6) . ?
N4 N5 1.159(7) . ?
N4 N3 1.198(6) . ?
C1 C2 1.407(7) . ?
C1 C6 1.426(7) . ?
C7 C6 1.437(7) . ?
C7 H009 0.9300 . ?
C6 C5 1.410(7) . ?
C9 C8 1.512(7) . ?
C9 H00A 0.9700 . ?
C9 H00B 0.9700 . ?
C8 H00C 0.9700 . ?
C8 H00D 0.9700 . ?
C5 C4 1.377(8) . ?
C5 H00E 0.9300 . ?
C3 C2 1.364(7) . ?
C3 C4 1.403(8) . ?
C3 H00F 0.9300 . ?
C2 H00G 0.9300 . ?
C11 C12 1.373(8) . ?
C11 C16 1.385(9) . ?
C11 C10 1.503(8) . ?
C4 C17 1.508(7) . ?
C10 H00H 0.9700 . ?
C10 H00I 0.9700 . ?
C12 C13 1.388(10) . ?
C12 H00J 0.9300 . ?
C17 H00K 0.9600 . ?
C17 H00L 0.9600 . ?
C17 H00M 0.9600 . ?
C16 C15 1.382(10) . ?
C16 H00N 0.9300 . ?
C13 C14 1.360(12) . ?
C13 H00O 0.9300 . ?
C15 C14 1.356(12) . ?
C15 H00P 0.9300 . ?
C14 H00Q 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
O1 Cu1 N1 92.19(16) . . ?
O1 Cu1 N3 89.17(18) . . ?
N1 Cu1 N3 174.28(19) . . ?
O1 Cu1 N2 176.04(15) . . ?
N1 Cu1 N2 84.52(17) . . ?
N3 Cu1 N2 93.90(18) . . ?
C1 O1 Cu1 125.0(3) . . ?
C9 N2 C10 112.9(4) . . ?
C9 N2 Cu1 106.4(3) . . ?
C10 N2 Cu1 114.0(3) . . ?
C9 N2 H003 107.8 . . ?
C10 N2 H003 107.8 . . ?
Cu1 N2 H003 107.8 . . ?
C7 N1 C8 121.2(4) . . ?
C7 N1 Cu1 125.9(4) . . ?
C8 N1 Cu1 112.5(3) . . ?
N5 N4 N3 178.1(6) . . ?
N4 N3 Cu1 118.4(4) . . ?
O1 C1 C2 118.1(5) . . ?
O1 C1 C6 125.5(5) . . ?
C2 C1 C6 116.4(5) . . ?
N1 C7 C6 124.9(5) . . ?
N1 C7 H009 117.5 . . ?
C6 C7 H009 117.5 . . ?
C5 C6 C1 120.0(5) . . ?
C5 C6 C7 118.6(5) . . ?
C1 C6 C7 121.4(5) . . ?
N2 C9 C8 109.0(4) . . ?
N2 C9 H00A 109.9 . . ?
C8 C9 H00A 109.9 . . ?
N2 C9 H00B 109.9 . . ?
C8 C9 H00B 109.9 . . ?
H00A C9 H00B 108.3 . . ?
N1 C8 C9 106.0(4) . . ?
N1 C8 H00C 110.5 . . ?
C9 C8 H00C 110.5 . . ?
N1 C8 H00D 110.5 . . ?
C9 C8 H00D 110.5 . . ?
H00C C8 H00D 108.7 . . ?
C4 C5 C6 122.4(5) . . ?
C4 C5 H00E 118.8 . . ?
C6 C5 H00E 118.8 . . ?
C2 C3 C4 122.4(5) . . ?
C2 C3 H00F 118.8 . . ?
C4 C3 H00F 118.8 . . ?
C3 C2 C1 122.0(5) . . ?
C3 C2 H00G 119.0 . . ?
C1 C2 H00G 119.0 . . ?
C12 C11 C16 119.2(6) . . ?
C12 C11 C10 121.3(6) . . ?
C16 C11 C10 119.5(6) . . ?
C5 C4 C3 116.7(5) . . ?
C5 C4 C17 121.9(5) . . ?
C3 C4 C17 121.4(5) . . ?
N2 C10 C11 113.4(5) . . ?
N2 C10 H00H 108.9 . . ?
C11 C10 H00H 108.9 . . ?
N2 C10 H00I 108.9 . . ?
C11 C10 H00I 108.9 . . ?
H00H C10 H00I 107.7 . . ?
C11 C12 C13 120.8(7) . . ?
C11 C12 H00J 119.6 . . ?
C13 C12 H00J 119.6 . . ?
C4 C17 H00K 109.5 . . ?
C4 C17 H00L 109.5 . . ?
H00K C17 H00L 109.5 . . ?
C4 C17 H00M 109.5 . . ?
H00K C17 H00M 109.5 . . ?
H00L C17 H00M 109.5 . . ?
C15 C16 C11 119.0(8) . . ?
C15 C16 H00N 120.5 . . ?
C11 C16 H00N 120.5 . . ?
C14 C13 C12 119.4(8) . . ?
C14 C13 H00O 120.3 . . ?
C12 C13 H00O 120.3 . . ?
C14 C15 C16 121.4(9) . . ?
C14 C15 H00P 119.3 . . ?
C16 C15 H00P 119.3 . . ?
C15 C14 C13 120.2(8) . . ?
C15 C14 H00Q 119.9 . . ?
C13 C14 H00Q 119.9 . . ?

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 -164.9(4) . . . . ?
Cu1 O1 C1 C6 13.6(7) . . . . ?
C8 N1 C7 C6 -179.1(5) . . . . ?
Cu1 N1 C7 C6 -6.7(8) . . . . ?
O1 C1 C6 C5 -175.6(5) . . . . ?
C2 C1 C6 C5 3.0(7) . . . . ?
O1 C1 C6 C7 7.2(8) . . . . ?
C2 C1 C6 C7 -174.2(5) . . . . ?
N1 C7 C6 C5 171.9(5) . . . . ?
N1 C7 C6 C1 -10.8(8) . . . . ?
C10 N2 C9 C8 87.2(5) . . . . ?
Cu1 N2 C9 C8 -38.5(4) . . . . ?
C7 N1 C8 C9 134.1(5) . . . . ?
Cu1 N1 C8 C9 -39.3(5) . . . . ?
N2 C9 C8 N1 50.9(5) . . . . ?
C1 C6 C5 C4 -1.3(8) . . . . ?
C7 C6 C5 C4 175.9(5) . . . . ?
C4 C3 C2 C1 -0.8(9) . . . . ?
O1 C1 C2 C3 176.7(5) . . . . ?
C6 C1 C2 C3 -2.0(8) . . . . ?
C6 C5 C4 C3 -1.5(8) . . . . ?
C6 C5 C4 C17 178.5(5) . . . . ?
C2 C3 C4 C5 2.6(8) . . . . ?
C2 C3 C4 C17 -177.4(6) . . . . ?
C9 N2 C10 C11 69.5(6) . . . . ?
Cu1 N2 C10 C11 -169.0(4) . . . . ?
C12 C11 C10 N2 -96.1(7) . . . . ?
C16 C11 C10 N2 83.2(7) . . . . ?
C16 C11 C12 C13 -0.8(9) . . . . ?
C10 C11 C12 C13 178.5(6) . . . . ?
C12 C11 C16 C15 1.3(10) . . . . ?
C10 C11 C16 C15 -178.0(6) . . . . ?
C11 C12 C13 C14 0.2(11) . . . . ?
C11 C16 C15 C14 -1.4(12) . . . . ?
C16 C15 C14 C13 0.9(13) . . . . ?
C12 C13 C14 C15 -0.3(13) . . . . ?

_refine_diff_density_max         0.495
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.091



