# 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 2022

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

data_f
_database_code_depnum_ccdc_archive 'CCDC 2126124'
loop_
_audit_author_name
_audit_author_address
'Paula Brandao'
;Associate Professor
Portugal
;
_audit_update_record             
;
2021-12-03 deposited with the CCDC.	2022-05-16 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 H23 Cl Cu N4 O6'
_chemical_formula_weight         478.38

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'
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'

_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                   7.5573(5)
_cell_length_b                   11.0009(9)
_cell_length_c                   12.5651(9)
_cell_angle_alpha                94.097(3)
_cell_angle_beta                 107.313(3)
_cell_angle_gamma                100.799(3)
_cell_volume                     970.58(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    547
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      25.12

_exptl_crystal_description       Plate
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_F_000             494
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.307
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6367
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43971
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.902
_diffrn_reflns_theta_max         27.138
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4276
_reflns_number_gt                3903
_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)+(0.0284P)²+0.8516P] 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         4276
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0249
_refine_ls_wR_factor_ref         0.0662
_refine_ls_wR_factor_gt          0.0637
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.002
_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 0.94120(3) 0.69433(2) 0.71773(2) 0.01893(7) Uani 1 1 d . . . . .
O1 O 0.87618(18) 0.51740(11) 0.72145(10) 0.0230(2) Uani 1 1 d . . . . .
O2 O 0.69124(18) 0.28702(11) 0.65893(11) 0.0256(3) Uani 1 1 d . . . . .
N1 N 0.9960(2) 0.72580(13) 0.87987(12) 0.0208(3) Uani 1 1 d . . . . .
N2 N 1.0311(2) 0.88152(13) 0.73161(12) 0.0206(3) Uani 1 1 d . . . . .
H2 H 1.141(3) 0.884(2) 0.730(2) 0.034(6) Uiso 1 1 d . . . . .
N3 N 0.8934(2) 0.66193(12) 0.55419(11) 0.0198(3) Uani 1 1 d . . . . .
N4 N 0.9363(2) 0.59856(13) 0.39629(12) 0.0218(3) Uani 1 1 d . . . . .
H4A H 0.992(3) 0.575(2) 0.359(2) 0.035(6) Uiso 1 1 d . . . . .
C1 C 0.7943(2) 0.46722(15) 0.79173(14) 0.0200(3) Uani 1 1 d . . . . .
C2 C 0.6901(2) 0.34086(16) 0.76062(15) 0.0220(3) Uani 1 1 d . . . . .
C3 C 0.5971(2) 0.28299(17) 0.82909(16) 0.0262(4) Uani 1 1 d . . . . .
H3 H 0.527196 0.199046 0.806729 0.031 Uiso 1 1 calc R U . . .
C4 C 0.6054(3) 0.34769(18) 0.93157(16) 0.0284(4) Uani 1 1 d . . . . .
H4 H 0.538997 0.308113 0.977573 0.034 Uiso 1 1 calc R U . . .
C5 C 0.7094(3) 0.46800(17) 0.96521(15) 0.0256(4) Uani 1 1 d . . . . .
H5 H 0.717212 0.510506 1.035519 0.031 Uiso 1 1 calc R U . . .
C6 C 0.8054(2) 0.52964(16) 0.89642(14) 0.0213(3) Uani 1 1 d . . . . .
C7 C 0.5715(3) 0.16626(17) 0.61501(18) 0.0325(4) Uani 1 1 d . . . . .
H7A H 0.609469 0.106933 0.667376 0.049 Uiso 1 1 calc R U . . .
H7B H 0.583526 0.138748 0.542059 0.049 Uiso 1 1 calc R U . . .
H7C H 0.439250 0.170159 0.605437 0.049 Uiso 1 1 calc R U . . .
C8 C 0.9216(2) 0.65412(16) 0.93851(14) 0.0223(3) Uani 1 1 d . . . . .
H8 H 0.944298 0.684916 1.015049 0.027 Uiso 1 1 calc R U . . .
C9 C 1.1164(3) 0.84969(16) 0.92829(14) 0.0242(3) Uani 1 1 d . . . . .
H9A H 1.251088 0.849238 0.937921 0.029 Uiso 1 1 calc R U . . .
H9B H 1.104806 0.875151 1.002684 0.029 Uiso 1 1 calc R U . . .
C10 C 1.0477(3) 0.93888(16) 0.84654(14) 0.0219(3) Uani 1 1 d . . . . .
H10 H 0.919(3) 0.9414(19) 0.8458(17) 0.025(5) Uiso 1 1 d . . . . .
C11 C 1.1692(3) 1.07062(16) 0.87335(15) 0.0268(4) Uani 1 1 d . . . . .
H11A H 1.299130 1.068471 0.872493 0.032 Uiso 1 1 calc R U . . .
H11B H 1.178004 1.107545 0.949450 0.032 Uiso 1 1 calc R U . . .
C12 C 1.0812(3) 1.15048(16) 0.78639(16) 0.0286(4) Uani 1 1 d . . . . .
H12A H 0.960214 1.163224 0.795784 0.034 Uiso 1 1 calc R U . . .
H12B H 1.168075 1.233394 0.799337 0.034 Uiso 1 1 calc R U . . .
C13 C 1.0438(3) 1.08957(16) 0.66689(16) 0.0284(4) Uani 1 1 d . . . . .
H13A H 1.166512 1.093381 0.652562 0.034 Uiso 1 1 calc R U . . .
H13B H 0.969330 1.137150 0.613236 0.034 Uiso 1 1 calc R U . . .
C14 C 0.9360(3) 0.95373(16) 0.64607(15) 0.0252(4) Uani 1 1 d . . . . .
H14A H 0.805154 0.950469 0.647851 0.030 Uiso 1 1 calc R U . . .
H14B H 0.927653 0.915585 0.570448 0.030 Uiso 1 1 calc R U . . .
C15 C 1.0206(2) 0.65004(15) 0.50301(14) 0.0204(3) Uani 1 1 d . . . . .
H15 H 1.154236 0.674959 0.537858 0.024 Uiso 1 1 calc R U . . .
C16 C 0.7437(3) 0.57488(17) 0.37635(15) 0.0264(4) Uani 1 1 d . . . . .
H16 H 0.647599 0.538321 0.307637 0.032 Uiso 1 1 calc R U . . .
C17 C 0.7179(3) 0.61416(17) 0.47451(15) 0.0253(4) Uani 1 1 d . . . . .
H17 H 0.598650 0.609561 0.486466 0.030 Uiso 1 1 calc R U . . .
Cl1 Cl 0.48116(6) 0.79004(4) 0.74897(4) 0.02940(11) Uani 1 1 d . . . . .
O101 O 0.3245(2) 0.70140(14) 0.76171(13) 0.0360(3) Uani 1 1 d . . . . .
O102 O 0.5875(2) 0.72737(16) 0.69424(14) 0.0422(4) Uani 1 1 d . . . . .
O103 O 0.4036(2) 0.87843(16) 0.67900(17) 0.0518(4) Uani 1 1 d . . . . .
O104 O 0.5994(3) 0.8522(3) 0.85656(17) 0.0798(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9236(12) . ?
Cu1 N1 1.9456(14) . ?
Cu1 N3 1.9711(14) . ?
Cu1 N2 2.0215(14) . ?
O1 C1 1.3170(19) . ?
O2 C2 1.372(2) . ?
O2 C7 1.427(2) . ?
N1 C8 1.282(2) . ?
N1 C9 1.464(2) . ?
N2 C14 1.476(2) . ?
N2 C10 1.494(2) . ?
N2 H2 0.83(2) . ?
N3 C15 1.326(2) . ?
N3 C17 1.382(2) . ?
N4 C15 1.331(2) . ?
N4 C16 1.371(2) . ?
N4 H4A 0.77(3) . ?
C1 C6 1.412(2) . ?
C1 C2 1.426(2) . ?
C2 C3 1.382(2) . ?
C3 C4 1.405(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.416(2) . ?
C5 H5 0.9500 . ?
C6 C8 1.448(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8 0.9500 . ?
C9 C10 1.518(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.518(2) . ?
C10 H10 0.98(2) . ?
C11 C12 1.527(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.522(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.525(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15 0.9500 . ?
C16 C17 1.358(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
Cl1 O104 1.4190(17) . ?
Cl1 O102 1.4361(15) . ?
Cl1 O101 1.4422(14) . ?
Cl1 O103 1.4461(18) . ?

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 90.38(5) . . ?
O1 Cu1 N3 89.54(5) . . ?
N1 Cu1 N3 178.32(6) . . ?
O1 Cu1 N2 173.42(6) . . ?
N1 Cu1 N2 84.04(6) . . ?
N3 Cu1 N2 95.94(6) . . ?
C1 O1 Cu1 123.70(10) . . ?
C2 O2 C7 117.32(14) . . ?
C8 N1 C9 122.01(15) . . ?
C8 N1 Cu1 125.24(12) . . ?
C9 N1 Cu1 112.36(10) . . ?
C14 N2 C10 110.15(13) . . ?
C14 N2 Cu1 121.05(11) . . ?
C10 N2 Cu1 109.12(10) . . ?
C14 N2 H2 109.3(16) . . ?
C10 N2 H2 107.1(16) . . ?
Cu1 N2 H2 98.8(16) . . ?
C15 N3 C17 105.86(14) . . ?
C15 N3 Cu1 126.63(12) . . ?
C17 N3 Cu1 125.40(12) . . ?
C15 N4 C16 107.94(15) . . ?
C15 N4 H4A 122.3(18) . . ?
C16 N4 H4A 128.7(18) . . ?
O1 C1 C6 124.30(15) . . ?
O1 C1 C2 117.72(15) . . ?
C6 C1 C2 117.97(15) . . ?
O2 C2 C3 125.30(16) . . ?
O2 C2 C1 113.79(14) . . ?
C3 C2 C1 120.90(16) . . ?
C2 C3 C4 120.31(17) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.00(16) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.81(17) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 119.95(16) . . ?
C1 C6 C8 121.37(15) . . ?
C5 C6 C8 118.60(15) . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C6 124.68(15) . . ?
N1 C8 H8 117.7 . . ?
C6 C8 H8 117.7 . . ?
N1 C9 C10 106.60(14) . . ?
N1 C9 H9A 110.4 . . ?
C10 C9 H9A 110.4 . . ?
N1 C9 H9B 110.4 . . ?
C10 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
N2 C10 C11 110.70(14) . . ?
N2 C10 C9 107.57(13) . . ?
C11 C10 C9 115.36(15) . . ?
N2 C10 H10 106.4(12) . . ?
C11 C10 H10 109.6(12) . . ?
C9 C10 H10 106.8(12) . . ?
C10 C11 C12 109.70(15) . . ?
C10 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C13 C12 C11 111.63(15) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 C14 112.40(15) . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
N2 C14 C13 111.28(15) . . ?
N2 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
N2 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N3 C15 N4 111.02(15) . . ?
N3 C15 H15 124.5 . . ?
N4 C15 H15 124.5 . . ?
C17 C16 N4 106.23(16) . . ?
C17 C16 H16 126.9 . . ?
N4 C16 H16 126.9 . . ?
C16 C17 N3 108.95(16) . . ?
C16 C17 H17 125.5 . . ?
N3 C17 H17 125.5 . . ?
O104 Cl1 O102 110.42(11) . . ?
O104 Cl1 O101 109.21(12) . . ?
O102 Cl1 O101 110.20(10) . . ?
O104 Cl1 O103 110.44(15) . . ?
O102 Cl1 O103 108.65(10) . . ?
O101 Cl1 O103 107.89(9) . . ?

_refine_diff_density_max         0.369
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.053

