# 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_Cu_CP_1
_database_code_depnum_ccdc_archive 'CCDC 2298698'
_audit_update_record             
;
2023-09-30 deposited with the CCDC.	2024-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C49 H55 Cl Cu2 N8 O16'
_chemical_formula_weight         1174.54

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

loop_
_symmetry_equiv_pos_as_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                   14.4011(8)
_cell_length_b                   16.9452(8)
_cell_length_c                   22.2478(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.857(2)
_cell_angle_gamma                90.00
_cell_volume                     5313.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    42125
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      28.92

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BLUE
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2432
_exptl_absorpt_coefficient_mu    0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_T_max  0.886
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            42125
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         28.92
_reflns_number_total             6977
_reflns_number_gt                4893
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT+ (Bruker, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL (1998)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0604P)²+5.1421P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6977
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1256
_refine_ls_wR_factor_gt          0.1119
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.59288(2) 0.469778(16) 0.703711(13) 0.03137(10) Uani 1 1 d . . .
O1 O 0.67051(12) 0.55580(10) 0.67869(8) 0.0388(4) Uani 1 1 d . . .
N1 N 0.69635(14) 0.45563(11) 0.77972(9) 0.0334(4) Uani 1 1 d . . .
C1 C 0.7531(2) 0.39233(16) 0.78930(13) 0.0476(7) Uani 1 1 d . . .
H1A H 0.7405 0.3501 0.7622 0.057 Uiso 1 1 calc R . .
Cl1 Cl 0.5000 0.57301(5) 0.7500 0.0384(2) Uani 1 2 d S . .
O1W O 0.9531(2) 0.64873(15) 1.07261(12) 0.0824(8) Uani 1 1 d . . .
H1WA H 0.9640 0.6932 1.0578 0.099 Uiso 1 1 d R . .
H1WB H 0.9267 0.6265 1.0392 0.099 Uiso 1 1 d R . .
N2 N 0.49700(14) 0.47898(11) 0.62171(9) 0.0327(4) Uani 1 1 d . . .
O2 O 0.73452(16) 0.45674(11) 0.63687(10) 0.0522(5) Uani 1 1 d . . .
C2 C 0.8289(2) 0.38753(18) 0.83749(16) 0.0603(9) Uani 1 1 d . . .
H2A H 0.8671 0.3427 0.8427 0.072 Uiso 1 1 calc R . .
O2W O 0.68098(19) 0.70980(15) 0.76869(13) 0.0843(8) Uani 1 1 d . . .
H2WA H 0.6386 0.7181 0.7895 0.101 Uiso 1 1 d R . .
H2WB H 0.6408 0.6910 0.7387 0.101 Uiso 1 1 d R . .
O3 O 0.54760(13) 0.36277(10) 0.71593(8) 0.0395(4) Uani 1 1 d . . .
N3 N 0.77383(17) 0.65328(13) 0.89056(11) 0.0449(5) Uani 1 1 d . . .
H3B H 0.7447 0.6561 0.8528 0.054 Uiso 1 1 calc R . .
C3 C 0.8485(2) 0.44961(17) 0.87831(14) 0.0523(7) Uani 1 1 d . . .
H3A H 0.8994 0.4470 0.9116 0.063 Uiso 1 1 calc R . .
O3W O 0.9085(4) 0.3530(3) 0.6900(3) 0.204(2) Uani 1 1 d . . .
H3WA H 0.9472 0.3165 0.7045 0.245 Uiso 1 1 d R . .
H3WB H 0.9095 0.3545 0.6519 0.245 Uiso 1 1 d R . .
N4 N 0.86699(17) 0.84884(12) 0.95406(10) 0.0439(5) Uani 1 1 d . . .
H4A H 0.8331 0.8881 0.9378 0.053 Uiso 1 1 calc R . .
C4 C 0.79087(18) 0.51594(14) 0.86869(11) 0.0360(5) Uani 1 1 d . . .
C5 C 0.71565(17) 0.51579(14) 0.81927(11) 0.0336(5) Uani 1 1 d . . .
H5A H 0.6762 0.5598 0.8130 0.040 Uiso 1 1 calc R . .
O5 O 0.85578(17) 0.57460(13) 0.96487(10) 0.0639(6) Uani 1 1 d . . .
O6 O 0.96920(17) 0.80399(11) 1.03713(10) 0.0630(6) Uani 1 1 d . . .
C6 C 0.80980(19) 0.58419(16) 0.91235(12) 0.0416(6) Uani 1 1 d . . .
C7 C 0.7818(2) 0.72428(16) 0.92797(14) 0.0485(7) Uani 1 1 d . . .
H7A H 0.7907 0.7095 0.9709 0.058 Uiso 1 1 calc R . .
H7B H 0.7231 0.7540 0.9174 0.058 Uiso 1 1 calc R . .
C8 C 0.8637(2) 0.77609(15) 0.91905(13) 0.0465(7) Uani 1 1 d . . .
H8A H 0.9228 0.7476 0.9321 0.056 Uiso 1 1 calc R . .
H8B H 0.8567 0.7886 0.8758 0.056 Uiso 1 1 calc R . .
C9 C 0.91982(19) 0.85734(15) 1.00992(12) 0.0391(6) Uani 1 1 d . . .
C10 C 0.36102(19) 0.50134(16) 0.51520(12) 0.0408(6) Uani 1 1 d . . .
H10A H 0.3141 0.5089 0.4802 0.049 Uiso 1 1 calc R . .
C11 C 0.42025(17) 0.56239(14) 0.53903(11) 0.0335(5) Uani 1 1 d . . .
C12 C 0.48577(18) 0.54899(14) 0.59296(11) 0.0357(5) Uani 1 1 d . . .
H12A H 0.5241 0.5908 0.6102 0.043 Uiso 1 1 calc R . .
C13 C 0.44083(19) 0.41935(14) 0.59649(11) 0.0379(6) Uani 1 1 d . . .
H13A H 0.4486 0.3700 0.6152 0.045 Uiso 1 1 calc R . .
C14 C 0.3721(2) 0.42869(16) 0.54387(12) 0.0447(6) Uani 1 1 d . . .
H14A H 0.3336 0.3865 0.5278 0.054 Uiso 1 1 calc R . .
C15 C 0.72627(18) 0.52830(15) 0.64617(11) 0.0377(6) Uani 1 1 d . . .
C16 C 0.77989(19) 0.58746(16) 0.61620(12) 0.0414(6) Uani 1 1 d . . .
C17 C 0.7535(2) 0.66622(18) 0.61308(15) 0.0570(8) Uani 1 1 d . . .
H17A H 0.7050 0.6831 0.6320 0.068 Uiso 1 1 calc R . .
C18 C 0.7985(3) 0.7196(2) 0.58222(18) 0.0776(11) Uani 1 1 d . . .
H18A H 0.7801 0.7723 0.5802 0.093 Uiso 1 1 calc R . .
C19 C 0.8697(3) 0.6959(3) 0.55466(18) 0.0783(12) Uani 1 1 d . . .
H19A H 0.8998 0.7324 0.5340 0.094 Uiso 1 1 calc R . .
C20 C 0.8975(3) 0.6180(3) 0.55724(17) 0.0752(11) Uani 1 1 d . . .
H20A H 0.9460 0.6018 0.5382 0.090 Uiso 1 1 calc R . .
C21 C 0.8523(2) 0.5633(2) 0.58871(15) 0.0580(8) Uani 1 1 d . . .
H21A H 0.8712 0.5107 0.5910 0.070 Uiso 1 1 calc R . .
C22 C 0.5000 0.32926(19) 0.7500 0.0311(7) Uani 1 2 d S . .
C23 C 0.5000 0.24042(19) 0.7500 0.0308(7) Uani 1 2 d S . .
C24 C 0.5753(2) 0.19900(17) 0.73603(14) 0.0502(7) Uani 1 1 d . . .
H24A H 0.6263 0.2259 0.7259 0.060 Uiso 1 1 calc R . .
C25 C 0.5747(3) 0.11709(18) 0.73708(17) 0.0653(9) Uani 1 1 d . . .
H25A H 0.6263 0.0893 0.7288 0.078 Uiso 1 1 calc R . .
C26 C 0.5000 0.0773(2) 0.7500 0.0622(13) Uani 1 2 d S . .
H26A H 0.5000 0.0224 0.7500 0.075 Uiso 1 2 calc SR . .


_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 O3 1.9646(16) . ?
Cu1 O1 1.9850(17) . ?
Cu1 N1 2.025(2) . ?
Cu1 N2 2.055(2) . ?
Cu1 Cl1 2.5447(7) . ?
O1 C15 1.275(3) . ?
N1 C5 1.338(3) . ?
N1 C1 1.339(3) . ?
C1 C2 1.366(4) . ?
Cl1 Cu1 2.5447(7) 2_656 ?
N2 C12 1.342(3) . ?
N2 C13 1.343(3) . ?
O2 C15 1.240(3) . ?
C2 C3 1.381(4) . ?
O3 C22 1.257(2) . ?
N3 C6 1.331(3) . ?
N3 C7 1.454(3) . ?
C3 C4 1.388(4) . ?
N4 C9 1.325(3) . ?
N4 C8 1.454(3) . ?
C4 C5 1.376(3) . ?
C4 C6 1.499(3) . ?
O5 C6 1.230(3) . ?
O6 C9 1.230(3) . ?
C7 C8 1.516(4) . ?
C9 C11 1.506(3) 8_566 ?
C10 C11 1.376(4) . ?
C10 C14 1.381(4) . ?
C11 C12 1.384(3) . ?
C11 C9 1.506(3) 8_465 ?
C13 C14 1.378(4) . ?
C15 C16 1.503(3) . ?
C16 C21 1.375(4) . ?
C16 C17 1.386(4) . ?
C17 C18 1.376(4) . ?
C18 C19 1.360(6) . ?
C19 C20 1.377(6) . ?
C20 C21 1.400(5) . ?
C22 O3 1.257(2) 2_656 ?
C22 C23 1.505(4) . ?
C23 C24 1.380(3) . ?
C23 C24 1.380(3) 2_656 ?
C24 C25 1.388(4) . ?
C25 C26 1.349(4) . ?
C26 C25 1.349(4) 2_656 ?

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
O3 Cu1 O1 159.83(8) . . ?
O3 Cu1 N1 89.05(8) . . ?
O1 Cu1 N1 87.76(8) . . ?
O3 Cu1 N2 90.64(7) . . ?
O1 Cu1 N2 90.56(7) . . ?
N1 Cu1 N2 174.25(8) . . ?
O3 Cu1 Cl1 111.19(6) . . ?
O1 Cu1 Cl1 88.96(6) . . ?
N1 Cu1 Cl1 95.81(6) . . ?
N2 Cu1 Cl1 89.65(6) . . ?
C15 O1 Cu1 110.33(16) . . ?
C5 N1 C1 117.9(2) . . ?
C5 N1 Cu1 118.47(16) . . ?
C1 N1 Cu1 123.23(17) . . ?
N1 C1 C2 122.4(3) . . ?
Cu1 Cl1 Cu1 93.15(3) 2_656 . ?
C12 N2 C13 117.6(2) . . ?
C12 N2 Cu1 118.91(16) . . ?
C13 N2 Cu1 123.44(16) . . ?
C1 C2 C3 119.5(3) . . ?
C22 O3 Cu1 137.56(18) . . ?
C6 N3 C7 122.7(2) . . ?
C2 C3 C4 118.7(3) . . ?
C9 N4 C8 123.0(2) . . ?
C5 C4 C3 118.0(2) . . ?
C5 C4 C6 121.9(2) . . ?
C3 C4 C6 120.1(2) . . ?
N1 C5 C4 123.4(2) . . ?
O5 C6 N3 123.8(2) . . ?
O5 C6 C4 120.3(3) . . ?
N3 C6 C4 115.9(2) . . ?
N3 C7 C8 112.1(2) . . ?
N4 C8 C7 111.2(2) . . ?
O6 C9 N4 123.0(2) . . ?
O6 C9 C11 120.1(2) . 8_566 ?
N4 C9 C11 116.9(2) . 8_566 ?
C11 C10 C14 119.3(2) . . ?
C10 C11 C12 118.0(2) . . ?
C10 C11 C9 124.5(2) . 8_465 ?
C12 C11 C9 117.6(2) . 8_465 ?
N2 C12 C11 123.5(2) . . ?
N2 C13 C14 122.3(2) . . ?
C13 C14 C10 119.3(2) . . ?
O2 C15 O1 123.1(2) . . ?
O2 C15 C16 120.2(2) . . ?
O1 C15 C16 116.7(2) . . ?
C21 C16 C17 119.4(3) . . ?
C21 C16 C15 120.3(3) . . ?
C17 C16 C15 120.3(3) . . ?
C18 C17 C16 120.4(3) . . ?
C19 C18 C17 120.4(4) . . ?
C18 C19 C20 120.3(3) . . ?
C19 C20 C21 119.6(3) . . ?
C16 C21 C20 119.9(3) . . ?
O3 C22 O3 126.3(3) 2_656 . ?
O3 C22 C23 116.86(16) 2_656 . ?
O3 C22 C23 116.86(16) . . ?
C24 C23 C24 118.9(3) . 2_656 ?
C24 C23 C22 120.56(17) . . ?
C24 C23 C22 120.56(17) 2_656 . ?
C23 C24 C25 119.7(3) . . ?
C26 C25 C24 120.8(3) . . ?
C25 C26 C25 120.0(4) . 2_656 ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.92
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.065
####################################################################### 
# 
# 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_Cu_CP_2
_database_code_depnum_ccdc_archive 'CCDC 2298699'
_audit_update_record             
;
2023-09-30 deposited with the CCDC.	2024-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H24 Cu3 N4 O12'
_chemical_formula_weight         823.15

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3526(10)
_cell_length_b                   8.6543(10)
_cell_length_c                   10.7547(13)
_cell_angle_alpha                85.213(2)
_cell_angle_beta                 75.719(2)
_cell_angle_gamma                80.446(2)
_cell_volume                     742.20(15)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3804
_cell_measurement_theta_min      1.96
_cell_measurement_theta_max      25.00

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            GREEN
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             415
_exptl_absorpt_coefficient_mu    2.205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.650
_exptl_absorpt_correction_T_max  0.718
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3804
_diffrn_reflns_av_R_equivalents  0.0107
_diffrn_reflns_av_sigmaI/netI    0.0188
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2586
_reflns_number_gt                2399
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT+ (Bruker, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL (1998)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0504P)²+1.0983P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2586
_refine_ls_number_parameters     228
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0842
_refine_ls_wR_factor_gt          0.0830
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.041
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.0000 0.0000 0.02168(15) Uani 1 2 d S . .
O1 O 0.5324(3) 0.0671(3) 0.1585(2) 0.0375(6) Uani 1 1 d . . .
N1 N 1.0587(3) 0.2637(3) -0.0289(2) 0.0182(5) Uani 1 1 d . . .
C1 C 0.6339(3) 0.1473(3) 0.1785(3) 0.0216(6) Uani 1 1 d . . .
Cu2 Cu 0.87700(4) 0.15347(4) -0.06951(3) 0.01808(13) Uani 1 1 d . . .
O2 O 0.7312(3) 0.2227(2) 0.09632(19) 0.0267(5) Uani 1 1 d . . .
C2 C 0.6335(4) 0.1586(3) 0.3172(3) 0.0234(6) Uani 1 1 d . . .
N2 N 1.0430(6) 0.4253(4) 0.3369(3) 0.0731(14) Uani 1 1 d U . .
H2A H 1.0476 0.3251 0.3400 0.088 Uiso 1 1 calc R A 1
O3 O 0.9422(2) -0.0391(2) 0.1974(2) 0.0274(5) Uani 1 1 d . . .
C3 C 0.4828(4) 0.2102(5) 0.4022(3) 0.0440(9) Uani 1 1 d . . .
H3A H 0.3847 0.2304 0.3736 0.053 Uiso 1 1 calc R . .
O4 O 1.0733(3) 0.0933(2) 0.3017(2) 0.0265(5) Uani 1 1 d . . .
C4 C 0.4781(5) 0.2315(6) 0.5293(4) 0.0573(12) Uani 1 1 d . . .
H4A H 0.3772 0.2686 0.5849 0.069 Uiso 1 1 calc R . .
O5 O 1.1569(3) 0.6301(3) 0.2293(2) 0.0376(6) Uani 1 1 d . . .
C5 C 0.6202(5) 0.1987(5) 0.5739(3) 0.0474(10) Uani 1 1 d . . .
H5A H 0.6156 0.2121 0.6596 0.057 Uiso 1 1 calc R . .
O6 O 0.7067(3) 0.0531(3) -0.0975(2) 0.0310(5) Uani 1 1 d . . .
H6B H 0.7462 0.0013 -0.1649 0.042(11) Uiso 1 1 d R . .
C6 C 0.7700(4) 0.1459(4) 0.4916(3) 0.0300(7) Uani 1 1 d . . .
H6A H 0.8667 0.1242 0.5221 0.036 Uiso 1 1 calc R . .
C7 C 0.7787(3) 0.1243(3) 0.3625(3) 0.0199(6) Uani 1 1 d . . .
C8 C 0.9459(3) 0.0558(3) 0.2812(3) 0.0179(5) Uani 1 1 d . . .
C9 C 1.2059(4) 0.2695(4) -0.1142(3) 0.0268(7) Uani 1 1 d . . .
H9A H 1.2253 0.2212 -0.1917 0.032 Uiso 1 1 calc R . .
C10 C 1.0352(3) 0.3345(3) 0.0823(3) 0.0179(5) Uani 1 1 d . . .
H10A H 0.9349 0.3310 0.1430 0.021 Uiso 1 1 calc R . .
C11 C 1.1521(4) 0.4119(3) 0.1109(3) 0.0210(6) Uani 1 1 d . . .
C12 C 1.1189(4) 0.4984(4) 0.2324(3) 0.0290(7) Uani 1 1 d . . .
C13 C 0.9456(7) 0.5210(7) 0.4537(5) 0.0308(10) Uani 0.586(6) 1 d P . 1
H13A H 0.9329 0.6326 0.4315 0.037 Uiso 0.586(6) 1 calc PR . 1
H13B H 0.8361 0.4905 0.4882 0.037 Uiso 0.586(6) 1 calc PR . 1
C13' C 1.0823(10) 0.4530(10) 0.4705(8) 0.0308(10) Uani 0.414(6) 1 d P . 2
H13E H 1.1044 0.3555 0.5190 0.037 Uiso 0.414(6) 1 calc PR . 2
H13F H 1.1743 0.5121 0.4595 0.037 Uiso 0.414(6) 1 calc PR . 2
C17 C 1.3015(4) 0.4178(4) 0.0216(3) 0.0340(8) Uani 1 1 d . . .
H17A H 1.3821 0.4708 0.0375 0.041 Uiso 1 1 calc R . .
C18 C 1.3285(4) 0.3431(4) -0.0920(3) 0.0389(8) Uani 1 1 d . . .
H18A H 1.4292 0.3428 -0.1530 0.047 Uiso 1 1 calc R . .


_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 O6 1.892(2) . ?
Cu1 O6 1.892(2) 2_655 ?
Cu1 O1 1.940(2) 2_655 ?
Cu1 O1 1.940(2) . ?
O1 C1 1.248(4) . ?
N1 C10 1.346(3) . ?
N1 C9 1.346(4) . ?
N1 Cu2 2.069(2) . ?
C1 O2 1.262(4) . ?
C1 C2 1.502(4) . ?
Cu2 O6 1.880(2) . ?
Cu2 O3 1.9641(19) 2_755 ?
Cu2 O2 1.972(2) . ?
C2 C3 1.390(4) . ?
C2 C7 1.394(4) . ?
N2 C12 1.314(5) . ?
N2 C13 1.540(6) . ?
N2 C13' 1.596(9) . ?
N2 H2A 0.8600 . ?
O3 C8 1.279(3) . ?
O3 Cu2 1.9641(19) 2_755 ?
C3 C4 1.384(5) . ?
C3 H3A 0.9300 . ?
O4 C8 1.236(3) . ?
C4 C5 1.366(6) . ?
C4 H4A 0.9300 . ?
O5 C12 1.229(4) . ?
C5 C6 1.375(5) . ?
C5 H5A 0.9300 . ?
O6 H6B 0.8500 . ?
C6 C7 1.399(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.508(4) . ?
C9 C18 1.368(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.377(4) . ?
C10 H10A 0.9300 . ?
C11 C17 1.380(4) . ?
C11 C12 1.504(4) . ?
C13 C13 1.492(11) 2_766 ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13' C13' 1.496(16) 2_766 ?
C13' H13E 0.9700 . ?
C13' H13F 0.9700 . ?
C17 C18 1.383(5) . ?
C17 H17A 0.9300 . ?
C18 H18A 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
O6 Cu1 O6 180.0 . 2_655 ?
O6 Cu1 O1 86.95(9) . 2_655 ?
O6 Cu1 O1 93.05(9) 2_655 2_655 ?
O6 Cu1 O1 93.05(9) . . ?
O6 Cu1 O1 86.94(9) 2_655 . ?
O1 Cu1 O1 180.0 2_655 . ?
C1 O1 Cu1 131.2(2) . . ?
C10 N1 C9 116.9(2) . . ?
C10 N1 Cu2 122.01(18) . . ?
C9 N1 Cu2 121.10(18) . . ?
O1 C1 O2 127.4(3) . . ?
O1 C1 C2 115.2(3) . . ?
O2 C1 C2 117.3(2) . . ?
O6 Cu2 O3 95.65(9) . 2_755 ?
O6 Cu2 O2 89.56(8) . . ?
O3 Cu2 O2 161.52(10) 2_755 . ?
O6 Cu2 N1 177.11(9) . . ?
O3 Cu2 N1 86.62(8) 2_755 . ?
O2 Cu2 N1 87.74(9) . . ?
C1 O2 Cu2 128.52(19) . . ?
C3 C2 C7 119.1(3) . . ?
C3 C2 C1 118.3(3) . . ?
C7 C2 C1 122.5(2) . . ?
C12 N2 C13 119.3(4) . . ?
C12 N2 C13' 118.7(4) . . ?
C13 N2 C13' 46.6(3) . . ?
C12 N2 H2A 120.4 . . ?
C13 N2 H2A 120.4 . . ?
C13' N2 H2A 101.8 . . ?
C8 O3 Cu2 131.04(18) . 2_755 ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5A 120.1 . . ?
C6 C5 H5A 120.1 . . ?
Cu2 O6 Cu1 136.78(12) . . ?
Cu2 O6 H6B 107.9 . . ?
Cu1 O6 H6B 113.4 . . ?
C5 C6 C7 120.7(3) . . ?
C5 C6 H6A 119.6 . . ?
C7 C6 H6A 119.6 . . ?
C2 C7 C6 119.3(3) . . ?
C2 C7 C8 123.5(2) . . ?
C6 C7 C8 117.2(3) . . ?
O4 C8 O3 125.7(3) . . ?
O4 C8 C7 118.3(2) . . ?
O3 C8 C7 116.0(2) . . ?
N1 C9 C18 123.0(3) . . ?
N1 C9 H9A 118.5 . . ?
C18 C9 H9A 118.5 . . ?
N1 C10 C11 123.4(3) . . ?
N1 C10 H10A 118.3 . . ?
C11 C10 H10A 118.3 . . ?
C10 C11 C17 118.8(3) . . ?
C10 C11 C12 122.4(3) . . ?
C17 C11 C12 118.7(3) . . ?
O5 C12 N2 124.4(3) . . ?
O5 C12 C11 120.4(3) . . ?
N2 C12 C11 115.2(3) . . ?
C13 C13 N2 102.5(5) 2_766 . ?
C13 C13 H13A 111.3 2_766 . ?
N2 C13 H13A 111.3 . . ?
C13 C13 H13B 111.3 2_766 . ?
N2 C13 H13B 111.3 . . ?
H13A C13 H13B 109.2 . . ?
C13' C13' N2 97.7(7) 2_766 . ?
C13' C13' H13E 112.2 2_766 . ?
N2 C13' H13E 112.2 . . ?
C13' C13' H13F 112.2 2_766 . ?
N2 C13' H13F 112.2 . . ?
H13E C13' H13F 109.8 . . ?
C11 C17 C18 118.4(3) . . ?
C11 C17 H17A 120.8 . . ?
C18 C17 H17A 120.8 . . ?
C9 C18 C17 119.5(3) . . ?
C9 C18 H18A 120.2 . . ?
C17 C18 H18A 120.2 . . ?

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
O6 Cu1 O1 C1 14.0(3) . . . . ?
O6 Cu1 O1 C1 -166.0(3) 2_655 . . . ?
O1 Cu1 O1 C1 167(10) 2_655 . . . ?
Cu1 O1 C1 O2 9.4(5) . . . . ?
Cu1 O1 C1 C2 -173.0(2) . . . . ?
C10 N1 Cu2 O6 -18(2) . . . . ?
C9 N1 Cu2 O6 162.9(18) . . . . ?
C10 N1 Cu2 O3 -159.9(2) . . . 2_755 ?
C9 N1 Cu2 O3 21.0(2) . . . 2_755 ?
C10 N1 Cu2 O2 2.5(2) . . . . ?
C9 N1 Cu2 O2 -176.6(2) . . . . ?
O1 C1 O2 Cu2 -45.9(4) . . . . ?
C2 C1 O2 Cu2 136.6(2) . . . . ?
O6 Cu2 O2 C1 40.1(3) . . . . ?
O3 Cu2 O2 C1 -66.6(4) 2_755 . . . ?
N1 Cu2 O2 C1 -138.9(3) . . . . ?
O1 C1 C2 C3 -54.2(4) . . . . ?
O2 C1 C2 C3 123.6(3) . . . . ?
O1 C1 C2 C7 127.9(3) . . . . ?
O2 C1 C2 C7 -54.3(4) . . . . ?
C7 C2 C3 C4 1.9(6) . . . . ?
C1 C2 C3 C4 -176.1(4) . . . . ?
C2 C3 C4 C5 -1.6(7) . . . . ?
C3 C4 C5 C6 0.8(7) . . . . ?
O3 Cu2 O6 Cu1 151.08(19) 2_755 . . . ?
O2 Cu2 O6 Cu1 -11.2(2) . . . . ?
N1 Cu2 O6 Cu1 9(2) . . . . ?
O6 Cu1 O6 Cu2 -1(11) 2_655 . . . ?
O1 Cu1 O6 Cu2 173.5(2) 2_655 . . . ?
O1 Cu1 O6 Cu2 -6.5(2) . . . . ?
C4 C5 C6 C7 -0.4(6) . . . . ?
C3 C2 C7 C6 -1.4(5) . . . . ?
C1 C2 C7 C6 176.5(3) . . . . ?
C3 C2 C7 C8 175.1(3) . . . . ?
C1 C2 C7 C8 -7.1(4) . . . . ?
C5 C6 C7 C2 0.6(5) . . . . ?
C5 C6 C7 C8 -176.0(3) . . . . ?
Cu2 O3 C8 O4 -2.2(4) 2_755 . . . ?
Cu2 O3 C8 C7 178.89(19) 2_755 . . . ?
C2 C7 C8 O4 147.3(3) . . . . ?
C6 C7 C8 O4 -36.2(4) . . . . ?
C2 C7 C8 O3 -33.7(4) . . . . ?
C6 C7 C8 O3 142.8(3) . . . . ?
C10 N1 C9 C18 -0.2(5) . . . . ?
Cu2 N1 C9 C18 179.0(3) . . . . ?
C9 N1 C10 C11 0.7(4) . . . . ?
Cu2 N1 C10 C11 -178.5(2) . . . . ?
N1 C10 C11 C17 0.0(4) . . . . ?
N1 C10 C11 C12 176.2(3) . . . . ?
C13 N2 C12 O5 20.1(7) . . . . ?
C13' N2 C12 O5 -33.7(7) . . . . ?
C13 N2 C12 C11 -157.4(4) . . . . ?
C13' N2 C12 C11 148.8(4) . . . . ?
C10 C11 C12 O5 -134.8(3) . . . . ?
C17 C11 C12 O5 41.5(5) . . . . ?
C10 C11 C12 N2 42.9(5) . . . . ?
C17 C11 C12 N2 -140.9(4) . . . . ?
C12 N2 C13 C13 -108.0(6) . . . 2_766 ?
C13' N2 C13 C13 -4.9(6) . . . 2_766 ?
C12 N2 C13' C13' 109.3(8) . . . 2_766 ?
C13 N2 C13' C13' 4.8(5) . . . 2_766 ?
C10 C11 C17 C18 -1.2(5) . . . . ?
C12 C11 C17 C18 -177.5(3) . . . . ?
N1 C9 C18 C17 -1.0(6) . . . . ?
C11 C17 C18 C9 1.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.947
_refine_diff_density_rms         0.084



