# 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 2018

####################################################################### 
# 
# 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 1550052'
_audit_update_record             
;
2017-05-15 deposited with the CCDC.
2018-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H42 Cl2 Cu2 N6 O16'
_chemical_formula_weight         1060.77

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'
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                   8.3736(8)
_cell_length_b                   10.9069(9)
_cell_length_c                   14.1280(14)
_cell_angle_alpha                101.860(4)
_cell_angle_beta                 96.035(5)
_cell_angle_gamma                105.536(4)
_cell_volume                     1198.94(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9827
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      28.31

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.47
_exptl_absorpt_coefficient_mu    1.071
_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      273(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            33320
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_av_R_equivalents  0.1383
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.184
_diffrn_reflns_theta_max         28.316
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5960
_reflns_number_gt                5233
_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 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_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)+(0.0747P)²+1.1443P] 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     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5960
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1580
_refine_ls_wR_factor_gt          0.1471
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 0.43528(3) 0.30956(3) 0.82256(2) 0.02847(13) Uani 1 1 d . . . . .
CL1 Cl 0.26211(14) 0.75866(9) 0.73527(9) 0.0682(3) Uani 1 1 d . . . . .
O1 O 0.6554(2) 0.38860(19) 0.91489(13) 0.0332(4) Uani 1 1 d . . . . .
O1W O 0.3742(3) 0.5084(2) 0.88755(15) 0.0446(5) Uani 1 1 d . . . . .
N2 N 0.2103(3) 0.2272(2) 0.73100(15) 0.0297(4) Uani 1 1 d . . . . .
N1 N 0.3381(3) 0.2301(2) 0.92785(15) 0.0290(4) Uani 1 1 d . . . . .
N3 N 0.5418(3) 0.3883(2) 0.71909(16) 0.0319(4) Uani 1 1 d . . . . .
O2 O 0.8154(3) 0.2674(3) 0.8550(2) 0.0770(10) Uani 1 1 d . . . . .
C15 C 0.7021(4) 0.4959(4) 0.5779(3) 0.0487(7) Uani 1 1 d . . . . .
C4 C 0.3605(4) 0.1133(3) 1.0512(2) 0.0459(7) Uani 1 1 d . . . . .
H4 H 0.420412 0.068499 1.082807 0.055 Uiso 1 1 calc R U . . .
C7 C 0.1449(4) 0.0966(3) 0.7036(2) 0.0388(6) Uani 1 1 d . . . . .
H7 H 0.203656 0.045285 0.728017 0.047 Uiso 1 1 calc R U . . .
C3 C 0.2121(4) 0.1282(3) 1.0800(2) 0.0406(6) Uani 1 1 d . . . . .
C9 C -0.0978(4) 0.1080(3) 0.6046(2) 0.0442(7) Uani 1 1 d . . . . .
C8 C -0.0054(4) 0.0351(3) 0.6411(2) 0.0442(7) Uani 1 1 d . . . . .
H8 H -0.045215 -0.056024 0.623237 0.053 Uiso 1 1 calc R U . . .
C19 C 0.7926(3) 0.3627(3) 0.9085(2) 0.0373(6) Uani 1 1 d . . . . .
C5 C 0.4190(4) 0.1644(3) 0.9761(2) 0.0394(6) Uani 1 1 d . . . . .
H5 H 0.518701 0.153025 0.957968 0.047 Uiso 1 1 calc R U . . .
C1 C 0.1956(3) 0.2454(3) 0.9558(2) 0.0379(6) Uani 1 1 d . . . . .
H1 H 0.137637 0.290403 0.922966 0.045 Uiso 1 1 calc R U . . .
C2 C 0.1310(4) 0.1975(3) 1.0306(2) 0.0447(7) Uani 1 1 d . . . . .
H2 H 0.032379 0.211768 1.048277 0.054 Uiso 1 1 calc R U . . .
C10 C -0.0297(4) 0.2434(3) 0.6333(2) 0.0483(7) Uani 1 1 d . . . . .
H10 H -0.086671 0.296823 0.610482 0.058 Uiso 1 1 calc R U . . .
C11 C 0.1231(4) 0.2986(3) 0.6959(2) 0.0408(6) Uani 1 1 d . . . . .
H11 H 0.166779 0.389585 0.714275 0.049 Uiso 1 1 calc R U . . .
C14 C 0.7221(6) 0.5676(4) 0.6731(3) 0.0624(10) Uani 1 1 d . . . . .
H14 H 0.791699 0.653740 0.691806 0.075 Uiso 1 1 calc R U . . .
C16 C 0.6017(4) 0.3686(4) 0.5559(2) 0.0482(7) Uani 1 1 d . . . . .
H16 H 0.585469 0.315899 0.492779 0.058 Uiso 1 1 calc R U . . .
C6 C 0.1472(6) 0.0733(4) 1.1626(3) 0.0623(10) Uani 1 1 d . . . . .
H6A H 0.221337 0.028911 1.186750 0.093 Uiso 1 1 calc R U . . .
H6B H 0.141974 0.143548 1.214589 0.093 Uiso 1 1 calc R U . . .
H6C H 0.036751 0.012504 1.139112 0.093 Uiso 1 1 calc R U . . .
C17 C 0.5245(4) 0.3182(3) 0.6273(2) 0.0408(6) Uani 1 1 d . . . . .
H17 H 0.457274 0.231293 0.610561 0.049 Uiso 1 1 calc R U . . .
C18 C 0.7886(6) 0.5562(5) 0.5039(3) 0.0735(12) Uani 1 1 d . . . . .
H18A H 0.852376 0.645716 0.534034 0.110 Uiso 1 1 calc R U . . .
H18B H 0.862655 0.508095 0.479821 0.110 Uiso 1 1 calc R U . . .
H18C H 0.706094 0.553585 0.450273 0.110 Uiso 1 1 calc R U . . .
C12 C -0.2650(5) 0.0450(5) 0.5374(3) 0.0689(12) Uani 1 1 d . . . . .
H12A H -0.308750 0.111892 0.520370 0.103 Uiso 1 1 calc R U . . .
H12B H -0.250563 -0.010783 0.478936 0.103 Uiso 1 1 calc R U . . .
H12C H -0.342326 -0.006327 0.570194 0.103 Uiso 1 1 calc R U . . .
C13 C 0.6400(5) 0.5127(3) 0.7410(2) 0.0516(8) Uani 1 1 d . . . . .
H13 H 0.653437 0.564117 0.804254 0.062 Uiso 1 1 calc R U . . .
O3 O 0.2642(8) 0.8533(6) 0.8165(4) 0.156(2) Uani 1 1 d . . . . .
O6 O 0.1363(7) 0.7540(6) 0.6598(4) 0.148(2) Uani 1 1 d . . . . .
O4 O 0.2564(11) 0.6415(5) 0.7488(5) 0.195(4) Uani 1 1 d . . . . .
O5 O 0.4167(8) 0.8080(8) 0.7067(5) 0.175(3) Uani 1 1 d . . . . .
O2W O 0.5240(3) 0.1065(3) 0.7460(2) 0.0567(6) Uani 1 1 d . . . . .
C20 C 0.9403(3) 0.4614(3) 0.9740(2) 0.0387(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 O1 2.0056(17) . ?
CU1 N1 2.008(2) . ?
CU1 N3 2.013(2) . ?
CU1 N2 2.033(2) . ?
CU1 O1W 2.384(2) . ?
CL1 O4 1.320(4) . ?
CL1 O3 1.372(5) . ?
CL1 O5 1.397(6) . ?
CL1 O6 1.401(4) . ?
O1 C19 1.263(3) . ?
N2 C11 1.332(3) . ?
N2 C7 1.338(3) . ?
N1 C1 1.337(3) . ?
N1 C5 1.342(3) . ?
N3 C17 1.335(3) . ?
N3 C13 1.338(4) . ?
O2 C19 1.225(4) . ?
C15 C16 1.368(5) . ?
C15 C14 1.378(5) . ?
C15 C18 1.497(5) . ?
C4 C5 1.371(4) . ?
C4 C3 1.386(5) . ?
C7 C8 1.372(4) . ?
C3 C2 1.383(4) . ?
C3 C6 1.504(4) . ?
C9 C8 1.383(5) . ?
C9 C10 1.387(5) . ?
C9 C12 1.507(4) . ?
C19 C20 1.476(4) . ?
C1 C2 1.371(4) . ?
C10 C11 1.383(4) . ?
C14 C13 1.380(5) . ?
C16 C17 1.384(4) . ?
C20 C20 1.179(6) 2_767 ?

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 88.55(8) . . ?
O1 CU1 N3 89.48(9) . . ?
N1 CU1 N3 177.65(8) . . ?
O1 CU1 N2 178.79(8) . . ?
N1 CU1 N2 90.26(9) . . ?
N3 CU1 N2 91.72(9) . . ?
O1 CU1 O1W 86.15(8) . . ?
N1 CU1 O1W 91.02(8) . . ?
N3 CU1 O1W 90.12(8) . . ?
N2 CU1 O1W 94.06(9) . . ?
O4 CL1 O3 116.8(4) . . ?
O4 CL1 O5 106.7(6) . . ?
O3 CL1 O5 103.3(4) . . ?
O4 CL1 O6 112.6(4) . . ?
O3 CL1 O6 109.3(4) . . ?
O5 CL1 O6 107.1(4) . . ?
C19 O1 CU1 128.68(17) . . ?
C11 N2 C7 117.5(2) . . ?
C11 N2 CU1 122.45(19) . . ?
C7 N2 CU1 120.02(19) . . ?
C1 N1 C5 117.4(2) . . ?
C1 N1 CU1 121.75(18) . . ?
C5 N1 CU1 120.76(19) . . ?
C17 N3 C13 117.0(3) . . ?
C17 N3 CU1 122.00(19) . . ?
C13 N3 CU1 120.9(2) . . ?
C16 C15 C14 116.8(3) . . ?
C16 C15 C18 122.6(4) . . ?
C14 C15 C18 120.6(4) . . ?
C5 C4 C3 120.2(3) . . ?
N2 C7 C8 122.8(3) . . ?
C2 C3 C4 116.7(3) . . ?
C2 C3 C6 122.6(3) . . ?
C4 C3 C6 120.7(3) . . ?
C8 C9 C10 116.7(3) . . ?
C8 C9 C12 122.2(3) . . ?
C10 C9 C12 121.0(3) . . ?
C7 C8 C9 120.4(3) . . ?
O2 C19 O1 127.6(3) . . ?
O2 C19 C20 118.0(3) . . ?
O1 C19 C20 114.3(2) . . ?
N1 C5 C4 122.6(3) . . ?
N1 C1 C2 122.8(3) . . ?
C1 C2 C3 120.2(3) . . ?
C11 C10 C9 119.8(3) . . ?
N2 C11 C10 122.8(3) . . ?
C15 C14 C13 120.6(3) . . ?
C15 C16 C17 120.1(3) . . ?
N3 C17 C16 123.1(3) . . ?
N3 C13 C14 122.4(3) . . ?
C20 C20 C19 178.7(4) 2_767 . ?

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
C11 N2 C7 C8 0.6(4) . . . . ?
CU1 N2 C7 C8 -179.2(2) . . . . ?
C5 C4 C3 C2 -0.9(5) . . . . ?
C5 C4 C3 C6 -179.6(3) . . . . ?
N2 C7 C8 C9 -1.1(5) . . . . ?
C10 C9 C8 C7 0.9(5) . . . . ?
C12 C9 C8 C7 -178.8(3) . . . . ?
CU1 O1 C19 O2 -14.9(5) . . . . ?
CU1 O1 C19 C20 164.7(2) . . . . ?
C1 N1 C5 C4 0.3(4) . . . . ?
CU1 N1 C5 C4 177.3(2) . . . . ?
C3 C4 C5 N1 0.1(5) . . . . ?
C5 N1 C1 C2 0.2(4) . . . . ?
CU1 N1 C1 C2 -176.8(2) . . . . ?
N1 C1 C2 C3 -1.1(5) . . . . ?
C4 C3 C2 C1 1.4(5) . . . . ?
C6 C3 C2 C1 -179.9(3) . . . . ?
C8 C9 C10 C11 -0.4(5) . . . . ?
C12 C9 C10 C11 179.3(3) . . . . ?
C7 N2 C11 C10 -0.1(5) . . . . ?
CU1 N2 C11 C10 179.8(2) . . . . ?
C9 C10 C11 N2 0.0(5) . . . . ?
C16 C15 C14 C13 -1.7(6) . . . . ?
C18 C15 C14 C13 178.8(4) . . . . ?
C14 C15 C16 C17 0.8(5) . . . . ?
C18 C15 C16 C17 -179.8(3) . . . . ?
C13 N3 C17 C16 -0.4(5) . . . . ?
CU1 N3 C17 C16 -177.4(2) . . . . ?
C15 C16 C17 N3 0.3(5) . . . . ?
C17 N3 C13 C14 -0.6(5) . . . . ?
CU1 N3 C13 C14 176.4(3) . . . . ?
C15 C14 C13 N3 1.7(7) . . . . ?

_refine_diff_density_max         0.742
_refine_diff_density_min         -0.765
_refine_diff_density_rms         0.094

