# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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_yxy15
_database_code_depnum_ccdc_archive 'CCDC 1015413'
_audit_update_record             
;
2014-07-22 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H28 Cu2 N12 O'
_chemical_formula_weight         723.74

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           Orthorhombic
_symmetry_space_group_name_H-M   'Pbcn '

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

_cell_length_a                   8.22470(10)
_cell_length_b                   33.0397(5)
_cell_length_c                   11.3562(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3085.95(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5829
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      27.65

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1480
_exptl_absorpt_coefficient_mu    1.428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8084
_exptl_absorpt_correction_T_max  0.9492
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16889
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.23
_diffrn_reflns_theta_max         27.66
_reflns_number_total             3583
_reflns_number_gt                2824
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0402P)²+4.4935P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3583
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0976
_refine_ls_wR_factor_gt          0.0827
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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 0.18613(4) 0.369784(8) 0.75297(2) 0.01432(10) Uani 1 1 d . . .
N1 N 0.0435(3) 0.36796(6) 0.89573(17) 0.0150(4) Uani 1 1 d . . .
N2 N 0.2099(3) 0.42808(6) 0.80887(18) 0.0203(5) Uani 1 1 d . . .
N3 N -0.1695(3) 0.31067(6) 0.80214(17) 0.0150(4) Uani 1 1 d . . .
N4 N 0.3401(3) 0.38160(6) 0.62378(18) 0.0201(5) Uani 1 1 d . . .
N5 N 0.4621(3) 0.36283(6) 0.61484(17) 0.0168(5) Uani 1 1 d . . .
N6 N 0.5847(3) 0.34585(7) 0.6021(2) 0.0270(5) Uani 1 1 d . . .
C1 C 0.2752(4) 0.45938(8) 0.7502(2) 0.0299(6) Uani 1 1 d . . .
H1A H 0.3088 0.4555 0.6729 0.036 Uiso 1 1 calc R . .
C2 C 0.2942(4) 0.49684(9) 0.8004(3) 0.0393(8) Uani 1 1 d . . .
H2A H 0.3373 0.5182 0.7571 0.047 Uiso 1 1 calc R . .
C3 C 0.2481(5) 0.50234(9) 0.9169(3) 0.0450(9) Uani 1 1 d . . .
H3A H 0.2614 0.5274 0.9529 0.054 Uiso 1 1 calc R . .
C4 C 0.1826(4) 0.47041(8) 0.9785(3) 0.0358(8) Uani 1 1 d . . .
H4A H 0.1522 0.4735 1.0569 0.043 Uiso 1 1 calc R . .
C5 C 0.1627(3) 0.43335(8) 0.9213(2) 0.0214(5) Uani 1 1 d . . .
C6 C 0.0862(3) 0.39811(7) 0.9723(2) 0.0192(5) Uani 1 1 d . . .
C7 C 0.0513(4) 0.38713(8) 1.0876(2) 0.0257(6) Uani 1 1 d . . .
H7A H 0.0691 0.4025 1.1549 0.031 Uiso 1 1 calc R . .
C8 C -0.0158(3) 0.34844(8) 1.0821(2) 0.0244(6) Uani 1 1 d . . .
H8A H -0.0511 0.3329 1.1454 0.029 Uiso 1 1 calc R . .
C9 C -0.0198(3) 0.33754(7) 0.9634(2) 0.0168(5) Uani 1 1 d . . .
C10 C -0.1007(3) 0.30347(7) 0.90814(19) 0.0155(5) Uani 1 1 d . . .
C11 C -0.1080(3) 0.26519(7) 0.9602(2) 0.0198(5) Uani 1 1 d . . .
H11A H -0.0598 0.2608 1.0332 0.024 Uiso 1 1 calc R . .
C12 C -0.1868(3) 0.23399(7) 0.9032(2) 0.0234(6) Uani 1 1 d . . .
H12A H -0.1953 0.2086 0.9378 0.028 Uiso 1 1 calc R . .
C13 C -0.2532(4) 0.24144(7) 0.7932(2) 0.0234(6) Uani 1 1 d . . .
H13A H -0.3043 0.2208 0.7517 0.028 Uiso 1 1 calc R . .
C14 C -0.2425(4) 0.27985(7) 0.7458(2) 0.0202(5) Uani 1 1 d . . .
H14A H -0.2877 0.2846 0.6720 0.024 Uiso 1 1 calc R . .
O1S O 0.5000 0.57754(8) 0.7500 0.0467(10) Uani 1 2 d S . .
C1S C 0.5573(5) 0.60197(8) 0.6567(3) 0.0412(9) Uani 1 1 d . . .
H1 H 0.4884 0.5990 0.5879 0.049 Uiso 1 1 calc R . .
H2 H 0.6675 0.5945 0.6356 0.049 Uiso 1 1 calc R . .
C2S C 0.5517(7) 0.64456(10) 0.7017(4) 0.0809(18) Uani 1 1 d . . .
H3 H 0.6596 0.6534 0.7247 0.097 Uiso 1 1 calc R . .
H4 H 0.5111 0.6627 0.6412 0.097 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 N4 1.977(2) . ?
Cu1 N1 2.002(2) . ?
Cu1 N2 2.037(2) . ?
Cu1 N3 2.0555(19) 4_556 ?
N1 C9 1.368(3) . ?
N1 C6 1.368(3) . ?
N2 C1 1.342(3) . ?
N2 C5 1.346(3) . ?
N3 C14 1.344(3) . ?
N3 C10 1.351(3) . ?
N3 Cu1 2.0555(19) 4_556 ?
N4 N5 1.184(3) . ?
N5 N6 1.163(3) . ?
C1 C2 1.372(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.388(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.376(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.396(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.445(3) . ?
C6 C7 1.388(3) . ?
C7 C8 1.394(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.396(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.450(3) . ?
C10 C11 1.398(3) . ?
C11 C12 1.379(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.385(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.381(3) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
O1S C1S 1.412(3) . ?
O1S C1S 1.412(3) 4_656 ?
C1S C2S 1.498(4) . ?
C1S H1 0.9700 . ?
C1S H2 0.9700 . ?
C2S C2S 1.388(8) 4_656 ?
C2S H3 0.9700 . ?
C2S H4 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
N4 Cu1 N1 169.18(8) . . ?
N4 Cu1 N2 89.03(9) . . ?
N1 Cu1 N2 80.35(8) . . ?
N4 Cu1 N3 90.24(8) . 4_556 ?
N1 Cu1 N3 100.31(8) . 4_556 ?
N2 Cu1 N3 178.24(9) . 4_556 ?
C9 N1 C6 106.0(2) . . ?
C9 N1 Cu1 134.42(16) . . ?
C6 N1 Cu1 110.02(16) . . ?
C1 N2 C5 119.1(2) . . ?
C1 N2 Cu1 127.76(18) . . ?
C5 N2 Cu1 112.96(16) . . ?
C14 N3 C10 118.6(2) . . ?
C14 N3 Cu1 123.04(17) . 4_556 ?
C10 N3 Cu1 117.79(15) . 4_556 ?
N5 N4 Cu1 120.21(17) . . ?
N6 N5 N4 176.6(2) . . ?
N2 C1 C2 122.3(3) . . ?
N2 C1 H1A 118.8 . . ?
C2 C1 H1A 118.8 . . ?
C1 C2 C3 118.9(3) . . ?
C1 C2 H2A 120.6 . . ?
C3 C2 H2A 120.6 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C3 C4 C5 118.8(3) . . ?
C3 C4 H4A 120.6 . . ?
C5 C4 H4A 120.6 . . ?
N2 C5 C4 121.4(2) . . ?
N2 C5 C6 113.7(2) . . ?
C4 C5 C6 124.8(2) . . ?
N1 C6 C7 110.9(2) . . ?
N1 C6 C5 116.3(2) . . ?
C7 C6 C5 132.7(2) . . ?
C6 C7 C8 106.2(2) . . ?
C6 C7 H7A 126.9 . . ?
C8 C7 H7A 126.9 . . ?
C7 C8 C9 106.8(2) . . ?
C7 C8 H8A 126.6 . . ?
C9 C8 H8A 126.6 . . ?
N1 C9 C8 110.1(2) . . ?
N1 C9 C10 120.1(2) . . ?
C8 C9 C10 129.0(2) . . ?
N3 C10 C11 121.2(2) . . ?
N3 C10 C9 116.2(2) . . ?
C11 C10 C9 122.7(2) . . ?
C12 C11 C10 119.9(2) . . ?
C12 C11 H11A 120.1 . . ?
C10 C11 H11A 120.1 . . ?
C11 C12 C13 118.4(2) . . ?
C11 C12 H12A 120.8 . . ?
C13 C12 H12A 120.8 . . ?
C14 C13 C12 119.3(2) . . ?
C14 C13 H13A 120.3 . . ?
C12 C13 H13A 120.3 . . ?
N3 C14 C13 122.6(2) . . ?
N3 C14 H14A 118.7 . . ?
C13 C14 H14A 118.7 . . ?
C1S O1S C1S 110.3(3) . 4_656 ?
O1S C1S C2S 105.7(3) . . ?
O1S C1S H1 110.6 . . ?
C2S C1S H1 110.6 . . ?
O1S C1S H2 110.6 . . ?
C2S C1S H2 110.6 . . ?
H1 C1S H2 108.7 . . ?
C2S C2S C1S 106.7(2) 4_656 . ?
C2S C2S H3 110.4 4_656 . ?
C1S C2S H3 110.4 . . ?
C2S C2S H4 110.4 4_656 . ?
C1S C2S H4 110.4 . . ?
H3 C2S H4 108.6 . . ?

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
N4 Cu1 N1 C9 -151.8(4) . . . . ?
N2 Cu1 N1 C9 -163.0(3) . . . . ?
N3 Cu1 N1 C9 15.3(3) 4_556 . . . ?
N4 Cu1 N1 C6 -11.6(5) . . . . ?
N2 Cu1 N1 C6 -22.84(17) . . . . ?
N3 Cu1 N1 C6 155.50(17) 4_556 . . . ?
N4 Cu1 N2 C1 14.2(3) . . . . ?
N1 Cu1 N2 C1 -167.9(3) . . . . ?
N3 Cu1 N2 C1 80(3) 4_556 . . . ?
N4 Cu1 N2 C5 -160.9(2) . . . . ?
N1 Cu1 N2 C5 17.00(19) . . . . ?
N3 Cu1 N2 C5 -95(3) 4_556 . . . ?
N1 Cu1 N4 N5 110.2(5) . . . . ?
N2 Cu1 N4 N5 121.3(2) . . . . ?
N3 Cu1 N4 N5 -57.1(2) 4_556 . . . ?
Cu1 N4 N5 N6 -166(4) . . . . ?
C5 N2 C1 C2 -0.7(5) . . . . ?
Cu1 N2 C1 C2 -175.6(3) . . . . ?
N2 C1 C2 C3 1.7(6) . . . . ?
C1 C2 C3 C4 -0.9(6) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
C1 N2 C5 C4 -1.0(4) . . . . ?
Cu1 N2 C5 C4 174.5(2) . . . . ?
C1 N2 C5 C6 176.7(3) . . . . ?
Cu1 N2 C5 C6 -7.7(3) . . . . ?
C3 C4 C5 N2 1.8(5) . . . . ?
C3 C4 C5 C6 -175.8(3) . . . . ?
C9 N1 C6 C7 0.2(3) . . . . ?
Cu1 N1 C6 C7 -151.4(2) . . . . ?
C9 N1 C6 C5 177.7(2) . . . . ?
Cu1 N1 C6 C5 26.1(3) . . . . ?
N2 C5 C6 N1 -12.4(4) . . . . ?
C4 C5 C6 N1 165.3(3) . . . . ?
N2 C5 C6 C7 164.3(3) . . . . ?
C4 C5 C6 C7 -18.0(5) . . . . ?
N1 C6 C7 C8 0.1(3) . . . . ?
C5 C6 C7 C8 -176.8(3) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C6 N1 C9 C8 -0.4(3) . . . . ?
Cu1 N1 C9 C8 140.8(2) . . . . ?
C6 N1 C9 C10 170.3(2) . . . . ?
Cu1 N1 C9 C10 -48.5(4) . . . . ?
C7 C8 C9 N1 0.5(3) . . . . ?
C7 C8 C9 C10 -169.2(3) . . . . ?
C14 N3 C10 C11 -1.6(4) . . . . ?
Cu1 N3 C10 C11 169.65(19) 4_556 . . . ?
C14 N3 C10 C9 178.4(2) . . . . ?
Cu1 N3 C10 C9 -10.4(3) 4_556 . . . ?
N1 C9 C10 N3 -27.1(3) . . . . ?
C8 C9 C10 N3 141.7(3) . . . . ?
N1 C9 C10 C11 152.9(2) . . . . ?
C8 C9 C10 C11 -38.3(4) . . . . ?
N3 C10 C11 C12 -0.1(4) . . . . ?
C9 C10 C11 C12 180.0(2) . . . . ?
C10 C11 C12 C13 1.8(4) . . . . ?
C11 C12 C13 C14 -1.8(4) . . . . ?
C10 N3 C14 C13 1.6(4) . . . . ?
Cu1 N3 C14 C13 -169.2(2) 4_556 . . . ?
C12 C13 C14 N3 0.2(4) . . . . ?
C1S O1S C1S C2S 6.6(3) 4_656 . . . ?
O1S C1S C2S C2S -18.3(7) . . . 4_656 ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.66
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.775
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.077
####################################################################### 
# 
# 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_yxy10_0m
_database_code_depnum_ccdc_archive 'CCDC 1015414'
_audit_update_record             
;
2014-07-22 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 Cu N4 O3'
_chemical_formula_weight         345.80

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           Monoclinic
_symmetry_space_group_name_H-M   'C2/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                   17.6233(3)
_cell_length_b                   12.3436(2)
_cell_length_c                   15.2939(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 123.0260(10)
_cell_angle_gamma                90.00
_cell_volume                     2789.40(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      27.49

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1400
_exptl_absorpt_coefficient_mu    1.584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6694
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20205
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_sigmaI/netI    0.0082
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3199
_reflns_number_gt                3043
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0368P)²+2.9288P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3199
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0215
_refine_ls_R_factor_gt           0.0205
_refine_ls_wR_factor_ref         0.0654
_refine_ls_wR_factor_gt          0.0645
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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 1.072584(10) 0.753300(11) 0.230649(11) 0.01120(7) Uani 1 1 d . . .
N1 N 1.04557(7) 0.91116(8) 0.19089(8) 0.0130(2) Uani 1 1 d . . .
N2 N 0.91217(8) 0.75868(8) 0.13071(9) 0.0126(2) Uani 1 1 d . . .
N3 N 0.89602(7) 0.59748(9) 0.22902(8) 0.0154(2) Uani 1 1 d . . .
N4 N 1.15775(8) 0.73191(9) 0.12967(9) 0.0168(2) Uani 1 1 d . . .
O1 O 1.21594(8) 0.75720(8) 0.22083(9) 0.0247(2) Uani 1 1 d . . .
O2 O 1.07430(7) 0.72858(8) 0.10181(7) 0.01710(19) Uani 1 1 d . . .
O3 O 1.17583(8) 0.70973(10) 0.06447(9) 0.0313(3) Uani 1 1 d . . .
C1 C 1.10467(9) 0.99276(11) 0.23768(10) 0.0160(2) Uani 1 1 d . . .
H1A H 1.1610 0.9779 0.2974 0.019 Uiso 1 1 calc R . .
C2 C 1.08540(9) 1.09779(11) 0.20092(10) 0.0193(3) Uani 1 1 d . . .
H2A H 1.1274 1.1529 0.2358 0.023 Uiso 1 1 calc R . .
C3 C 1.00152(10) 1.11942(11) 0.11041(11) 0.0205(3) Uani 1 1 d . . .
H3A H 0.9873 1.1891 0.0829 0.025 Uiso 1 1 calc R . .
C4 C 0.93970(9) 1.03627(11) 0.06204(10) 0.0179(3) Uani 1 1 d . . .
H4A H 0.8834 1.0495 0.0016 0.021 Uiso 1 1 calc R . .
C5 C 0.96245(8) 0.93211(10) 0.10469(9) 0.0132(2) Uani 1 1 d . . .
C6 C 0.90198(8) 0.83915(10) 0.06293(9) 0.0139(2) Uani 1 1 d . . .
C7 C 0.84502(8) 0.80384(11) -0.03950(10) 0.0175(3) Uani 1 1 d . . .
H7A H 0.8265 0.8436 -0.0996 0.021 Uiso 1 1 calc R . .
C8 C 0.82086(8) 0.69691(12) -0.03477(10) 0.0182(3) Uani 1 1 d . . .
H8A H 0.7842 0.6515 -0.0910 0.022 Uiso 1 1 calc R . .
C9 C 0.86228(8) 0.67198(10) 0.07026(9) 0.0145(2) Uani 1 1 d . . .
C10 C 0.86152(8) 0.57835(10) 0.12670(10) 0.0156(2) Uani 1 1 d . . .
C11 C 0.83211(10) 0.47490(11) 0.08478(11) 0.0227(3) Uani 1 1 d . . .
H11A H 0.8079 0.4622 0.0144 0.027 Uiso 1 1 calc R . .
C12 C 0.83937(11) 0.39167(12) 0.14913(13) 0.0288(3) Uani 1 1 d . . .
H12A H 0.8199 0.3223 0.1223 0.035 Uiso 1 1 calc R . .
C13 C 0.87584(11) 0.41182(12) 0.25412(13) 0.0278(3) Uani 1 1 d . . .
H13A H 0.8815 0.3564 0.2985 0.033 Uiso 1 1 calc R . .
C14 C 0.90349(10) 0.51582(11) 0.29112(11) 0.0212(3) Uani 1 1 d . . .
H14A H 0.9281 0.5297 0.3614 0.025 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 N2 1.9878(12) 2_755 ?
Cu1 N3 2.0035(11) 2_755 ?
Cu1 O2 2.0104(10) . ?
Cu1 N1 2.0194(10) . ?
Cu1 N2 2.3712(12) . ?
Cu1 Cu1 2.9234(3) 2_755 ?
N1 C1 1.3413(16) . ?
N1 C5 1.3585(15) . ?
N2 C9 1.3737(15) . ?
N2 C6 1.3750(16) . ?
N2 Cu1 1.9878(12) 2_755 ?
N3 C14 1.3413(17) . ?
N3 C10 1.3554(16) . ?
N3 Cu1 2.0035(11) 2_755 ?
N4 O3 1.2318(16) . ?
N4 O1 1.2387(17) . ?
N4 O2 1.2896(15) . ?
C1 C2 1.3799(18) . ?
C1 H1A 0.9300 . ?
C2 C3 1.3936(19) . ?
C2 H2A 0.9300 . ?
C3 C4 1.3818(19) . ?
C3 H3A 0.9300 . ?
C4 C5 1.3979(17) . ?
C4 H4A 0.9300 . ?
C5 C6 1.4555(17) . ?
C6 C7 1.3919(17) . ?
C7 C8 1.401(2) . ?
C7 H7A 0.9300 . ?
C8 C9 1.3891(17) . ?
C8 H8A 0.9300 . ?
C9 C10 1.4468(18) . ?
C10 C11 1.3958(18) . ?
C11 C12 1.380(2) . ?
C11 H11A 0.9300 . ?
C12 C13 1.389(2) . ?
C12 H12A 0.9300 . ?
C13 C14 1.380(2) . ?
C13 H13A 0.9300 . ?
C14 H14A 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
N2 Cu1 N3 81.35(4) 2_755 2_755 ?
N2 Cu1 O2 170.08(4) 2_755 . ?
N3 Cu1 O2 90.40(4) 2_755 . ?
N2 Cu1 N1 99.30(4) 2_755 . ?
N3 Cu1 N1 177.85(4) 2_755 . ?
O2 Cu1 N1 88.76(4) . . ?
N2 Cu1 N2 96.15(4) 2_755 . ?
N3 Cu1 N2 104.92(4) 2_755 . ?
O2 Cu1 N2 91.26(4) . . ?
N1 Cu1 N2 77.07(4) . . ?
N2 Cu1 Cu1 53.73(3) 2_755 2_755 ?
N3 Cu1 Cu1 93.61(3) 2_755 2_755 ?
O2 Cu1 Cu1 132.90(3) . 2_755 ?
N1 Cu1 Cu1 88.41(3) . 2_755 ?
N2 Cu1 Cu1 42.53(3) . 2_755 ?
C1 N1 C5 119.20(11) . . ?
C1 N1 Cu1 125.23(8) . . ?
C5 N1 Cu1 115.37(8) . . ?
C9 N2 C6 106.42(11) . . ?
C9 N2 Cu1 110.90(8) . 2_755 ?
C6 N2 Cu1 135.60(8) . 2_755 ?
C9 N2 Cu1 120.86(8) . . ?
C6 N2 Cu1 97.25(8) . . ?
Cu1 N2 Cu1 83.74(4) 2_755 . ?
C14 N3 C10 119.72(11) . . ?
C14 N3 Cu1 126.83(9) . 2_755 ?
C10 N3 Cu1 113.42(9) . 2_755 ?
O3 N4 O1 123.12(13) . . ?
O3 N4 O2 118.49(12) . . ?
O1 N4 O2 118.39(11) . . ?
N4 O2 Cu1 107.15(8) . . ?
N1 C1 C2 122.75(12) . . ?
N1 C1 H1A 118.6 . . ?
C2 C1 H1A 118.6 . . ?
C1 C2 C3 118.49(12) . . ?
C1 C2 H2A 120.8 . . ?
C3 C2 H2A 120.8 . . ?
C4 C3 C2 119.31(12) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C3 C4 C5 119.43(12) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
N1 C5 C4 120.75(11) . . ?
N1 C5 C6 114.84(11) . . ?
C4 C5 C6 124.41(11) . . ?
N2 C6 C7 109.88(11) . . ?
N2 C6 C5 118.37(11) . . ?
C7 C6 C5 130.33(11) . . ?
C6 C7 C8 106.85(11) . . ?
C6 C7 H7A 126.6 . . ?
C8 C7 H7A 126.6 . . ?
C9 C8 C7 106.59(11) . . ?
C9 C8 H8A 126.7 . . ?
C7 C8 H8A 126.7 . . ?
N2 C9 C8 110.23(11) . . ?
N2 C9 C10 115.56(11) . . ?
C8 C9 C10 134.18(12) . . ?
N3 C10 C11 120.68(12) . . ?
N3 C10 C9 113.92(11) . . ?
C11 C10 C9 125.35(12) . . ?
C12 C11 C10 119.13(13) . . ?
C12 C11 H11A 120.4 . . ?
C10 C11 H11A 120.4 . . ?
C11 C12 C13 119.74(13) . . ?
C11 C12 H12A 120.1 . . ?
C13 C12 H12A 120.1 . . ?
C14 C13 C12 118.57(14) . . ?
C14 C13 H13A 120.7 . . ?
C12 C13 H13A 120.7 . . ?
N3 C14 C13 122.15(13) . . ?
N3 C14 H14A 118.9 . . ?
C13 C14 H14A 118.9 . . ?

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
N2 Cu1 N1 C1 68.03(11) 2_755 . . . ?
N3 Cu1 N1 C1 -39.3(11) 2_755 . . . ?
O2 Cu1 N1 C1 -106.16(10) . . . . ?
N2 Cu1 N1 C1 162.27(11) . . . . ?
Cu1 Cu1 N1 C1 120.86(10) 2_755 . . . ?
N2 Cu1 N1 C5 -117.15(9) 2_755 . . . ?
N3 Cu1 N1 C5 135.5(11) 2_755 . . . ?
O2 Cu1 N1 C5 68.66(9) . . . . ?
N2 Cu1 N1 C5 -22.92(8) . . . . ?
Cu1 Cu1 N1 C5 -64.32(8) 2_755 . . . ?
N2 Cu1 N2 C9 -114.49(9) 2_755 . . . ?
N3 Cu1 N2 C9 -31.83(10) 2_755 . . . ?
O2 Cu1 N2 C9 58.91(10) . . . . ?
N1 Cu1 N2 C9 147.35(10) . . . . ?
Cu1 Cu1 N2 C9 -110.64(10) 2_755 . . . ?
N2 Cu1 N2 C6 131.44(6) 2_755 . . . ?
N3 Cu1 N2 C6 -145.91(7) 2_755 . . . ?
O2 Cu1 N2 C6 -55.16(8) . . . . ?
N1 Cu1 N2 C6 33.27(7) . . . . ?
Cu1 Cu1 N2 C6 135.29(9) 2_755 . . . ?
N2 Cu1 N2 Cu1 -3.85(6) 2_755 . . 2_755 ?
N3 Cu1 N2 Cu1 78.81(4) 2_755 . . 2_755 ?
O2 Cu1 N2 Cu1 169.55(4) . . . 2_755 ?
N1 Cu1 N2 Cu1 -102.01(4) . . . 2_755 ?
O3 N4 O2 Cu1 174.04(10) . . . . ?
O1 N4 O2 Cu1 -5.91(14) . . . . ?
N2 Cu1 O2 N4 -47.7(3) 2_755 . . . ?
N3 Cu1 O2 N4 -81.15(8) 2_755 . . . ?
N1 Cu1 O2 N4 96.88(8) . . . . ?
N2 Cu1 O2 N4 173.92(8) . . . . ?
Cu1 Cu1 O2 N4 -176.45(6) 2_755 . . . ?
C5 N1 C1 C2 -1.19(19) . . . . ?
Cu1 N1 C1 C2 173.44(10) . . . . ?
N1 C1 C2 C3 -1.1(2) . . . . ?
C1 C2 C3 C4 1.7(2) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C1 N1 C5 C4 2.86(17) . . . . ?
Cu1 N1 C5 C4 -172.29(9) . . . . ?
C1 N1 C5 C6 -177.14(11) . . . . ?
Cu1 N1 C5 C6 7.71(13) . . . . ?
C3 C4 C5 N1 -2.25(19) . . . . ?
C3 C4 C5 C6 177.76(12) . . . . ?
C9 N2 C6 C7 0.84(14) . . . . ?
Cu1 N2 C6 C7 -145.51(11) 2_755 . . . ?
Cu1 N2 C6 C7 126.05(9) . . . . ?
C9 N2 C6 C5 -166.95(11) . . . . ?
Cu1 N2 C6 C5 46.70(18) 2_755 . . . ?
Cu1 N2 C6 C5 -41.74(12) . . . . ?
N1 C5 C6 N2 29.13(16) . . . . ?
C4 C5 C6 N2 -150.87(12) . . . . ?
N1 C5 C6 C7 -135.74(14) . . . . ?
C4 C5 C6 C7 44.3(2) . . . . ?
N2 C6 C7 C8 -1.38(15) . . . . ?
C5 C6 C7 C8 164.48(13) . . . . ?
C6 C7 C8 C9 1.36(15) . . . . ?
C6 N2 C9 C8 0.04(14) . . . . ?
Cu1 N2 C9 C8 155.53(9) 2_755 . . . ?
Cu1 N2 C9 C8 -109.18(11) . . . . ?
C6 N2 C9 C10 -178.26(11) . . . . ?
Cu1 N2 C9 C10 -22.78(13) 2_755 . . . ?
Cu1 N2 C9 C10 72.51(13) . . . . ?
C7 C8 C9 N2 -0.89(15) . . . . ?
C7 C8 C9 C10 176.98(14) . . . . ?
C14 N3 C10 C11 1.17(19) . . . . ?
Cu1 N3 C10 C11 -176.92(10) 2_755 . . . ?
C14 N3 C10 C9 -176.53(12) . . . . ?
Cu1 N3 C10 C9 5.37(13) 2_755 . . . ?
N2 C9 C10 N3 11.73(16) . . . . ?
C8 C9 C10 N3 -166.06(14) . . . . ?
N2 C9 C10 C11 -165.86(12) . . . . ?
C8 C9 C10 C11 16.4(2) . . . . ?
N3 C10 C11 C12 -0.6(2) . . . . ?
C9 C10 C11 C12 176.82(13) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C11 C12 C13 C14 0.4(2) . . . . ?
C10 N3 C14 C13 -0.9(2) . . . . ?
Cu1 N3 C14 C13 176.87(11) 2_755 . . . ?
C12 C13 C14 N3 0.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.081
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1015415'
_audit_update_record             
;
2014-07-22 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C43 H30 Cu2 F3 N9 O3 S'
_chemical_formula_weight         936.90

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pca2(1) '

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

_cell_length_a                   18.6566(9)
_cell_length_b                   11.8775(6)
_cell_length_c                   19.2374(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4262.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4432
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      20.04

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1904
_exptl_absorpt_coefficient_mu    1.110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6664
_exptl_absorpt_correction_T_max  0.7456
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30751
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_sigmaI/netI    0.0882
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         27.53
_reflns_number_total             9179
_reflns_number_gt                5808
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0864P)²+1.6721P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.042(19)
_refine_ls_number_reflns         9179
_refine_ls_number_parameters     551
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_ref         0.1685
_refine_ls_wR_factor_gt          0.1546
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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 0.20854(4) 0.57838(6) 0.06642(4) 0.0381(2) Uani 1 1 d . . .
Cu2 Cu 0.22674(4) 0.34445(6) 0.05105(4) 0.0387(2) Uani 1 1 d . . .
N1 N 0.2481(3) 0.2114(5) -0.0257(3) 0.0466(14) Uani 1 1 d . . .
N2 N 0.3217(3) 0.3921(4) 0.0199(3) 0.0396(13) Uani 1 1 d . . .
N3 N 0.3048(3) 0.5835(4) 0.1194(3) 0.0388(13) Uani 1 1 d . . .
N4 N 0.2570(3) 0.6361(4) -0.0184(3) 0.0412(14) Uani 1 1 d . . .
N5 N 0.1645(3) 0.4515(4) -0.0163(3) 0.0329(12) Uani 1 1 d . . .
N6 N 0.1304(3) 0.2806(4) 0.0692(3) 0.0380(12) Uani 1 1 d . . .
N7 N 0.2576(3) 0.3341(5) 0.1532(3) 0.0431(14) Uani 1 1 d . . .
N8 N 0.1547(3) 0.5239(5) 0.1465(3) 0.0408(14) Uani 1 1 d . . .
N9 N 0.1222(3) 0.6903(4) 0.0580(4) 0.0484(13) Uani 1 1 d . . .
C1 C 0.2082(5) 0.1250(6) -0.0439(5) 0.063(2) Uani 1 1 d . . .
H1A H 0.1621 0.1206 -0.0257 0.075 Uiso 1 1 calc R . .
C2 C 0.2301(5) 0.0412(8) -0.0877(6) 0.076(3) Uani 1 1 d . . .
H2A H 0.2046 -0.0255 -0.0931 0.091 Uiso 1 1 calc R . .
C3 C 0.2922(7) 0.0627(9) -0.1232(6) 0.093(4) Uani 1 1 d . . .
H3A H 0.3067 0.0120 -0.1572 0.111 Uiso 1 1 calc R . .
C4 C 0.3384(5) 0.1651(8) -0.1096(5) 0.074(3) Uani 1 1 d . . .
H4A H 0.3803 0.1815 -0.1338 0.088 Uiso 1 1 calc R . .
C5 C 0.3109(4) 0.2313(5) -0.0567(4) 0.0407(16) Uani 1 1 d . . .
C6 C 0.3499(4) 0.3292(5) -0.0298(4) 0.0402(16) Uani 1 1 d . . .
C7 C 0.4193(4) 0.3616(7) -0.0471(5) 0.062(2) Uani 1 1 d . . .
H7A H 0.4481 0.3334 -0.0825 0.075 Uiso 1 1 calc R . .
C8 C 0.4362(4) 0.4474(7) 0.0015(5) 0.058(2) Uani 1 1 d . . .
H8A H 0.4798 0.4846 0.0059 0.070 Uiso 1 1 calc R . .
C9 C 0.3738(3) 0.4655(5) 0.0420(4) 0.0419(17) Uani 1 1 d . . .
C10 C 0.3662(4) 0.5398(5) 0.1010(4) 0.0408(16) Uani 1 1 d . . .
C11 C 0.4311(4) 0.5756(7) 0.1377(5) 0.055(2) Uani 1 1 d . . .
H11A H 0.4757 0.5487 0.1241 0.067 Uiso 1 1 calc R . .
C12 C 0.4251(5) 0.6499(7) 0.1931(5) 0.064(2) Uani 1 1 d . . .
H12A H 0.4660 0.6757 0.2158 0.077 Uiso 1 1 calc R . .
C13 C 0.3601(5) 0.6844(6) 0.2135(4) 0.056(2) Uani 1 1 d . . .
H13A H 0.3551 0.7307 0.2522 0.067 Uiso 1 1 calc R . .
C14 C 0.2992(4) 0.6492(6) 0.1754(4) 0.0510(19) Uani 1 1 d . . .
H14A H 0.2540 0.6726 0.1898 0.061 Uiso 1 1 calc R . .
C15 C 0.3076(3) 0.7184(6) -0.0180(4) 0.0499(19) Uani 1 1 d . . .
H15A H 0.3242 0.7443 0.0247 0.060 Uiso 1 1 calc R . .
C16 C 0.3348(4) 0.7640(6) -0.0755(5) 0.059(2) Uani 1 1 d . . .
H16A H 0.3662 0.8246 -0.0727 0.071 Uiso 1 1 calc R . .
C17 C 0.3161(4) 0.7214(7) -0.1373(5) 0.064(2) Uani 1 1 d . . .
H17A H 0.3368 0.7486 -0.1779 0.077 Uiso 1 1 calc R . .
C18 C 0.2641(5) 0.6339(7) -0.1400(4) 0.071(3) Uani 1 1 d . . .
H18A H 0.2504 0.6030 -0.1824 0.085 Uiso 1 1 calc R . .
C19 C 0.2346(4) 0.5960(6) -0.0794(4) 0.0457(17) Uani 1 1 d . . .
C20 C 0.1779(4) 0.5109(6) -0.0766(4) 0.0411(16) Uani 1 1 d . . .
C21 C 0.1263(5) 0.4899(8) -0.1234(4) 0.063(2) Uani 1 1 d . . .
H21A H 0.1235 0.5198 -0.1680 0.076 Uiso 1 1 calc R . .
C22 C 0.0780(4) 0.4157(7) -0.0935(4) 0.0524(19) Uani 1 1 d . . .
H22A H 0.0360 0.3886 -0.1134 0.063 Uiso 1 1 calc R . .
C23 C 0.1039(3) 0.3906(5) -0.0298(4) 0.0388(16) Uani 1 1 d . . .
C24 C 0.0817(4) 0.3077(6) 0.0209(4) 0.0487(18) Uani 1 1 d . . .
C25 C 0.0150(4) 0.2493(6) 0.0158(5) 0.059(2) Uani 1 1 d . . .
H25A H -0.0165 0.2637 -0.0206 0.070 Uiso 1 1 calc R . .
C26 C -0.0009(4) 0.1726(7) 0.0653(6) 0.073(3) Uani 1 1 d . . .
H26A H -0.0448 0.1356 0.0651 0.088 Uiso 1 1 calc R . .
C27 C 0.0481(5) 0.1508(7) 0.1154(5) 0.070(3) Uani 1 1 d . . .
H27A H 0.0376 0.0980 0.1496 0.084 Uiso 1 1 calc R . .
C28 C 0.1128(4) 0.2046(6) 0.1167(4) 0.0532(19) Uani 1 1 d . . .
H28A H 0.1454 0.1876 0.1518 0.064 Uiso 1 1 calc R . .
C29 C 0.3158(4) 0.2661(5) 0.1597(4) 0.0453(18) Uani 1 1 d . . .
H29A H 0.3395 0.2387 0.1207 0.054 Uiso 1 1 calc R . .
C30 C 0.3389(5) 0.2383(7) 0.2265(5) 0.068(3) Uani 1 1 d . . .
H30A H 0.3798 0.1942 0.2318 0.081 Uiso 1 1 calc R . .
C31 C 0.3044(4) 0.2730(7) 0.2819(5) 0.056(2) Uani 1 1 d . . .
H31A H 0.3183 0.2472 0.3255 0.067 Uiso 1 1 calc R . .
C32 C 0.2473(5) 0.3478(7) 0.2762(4) 0.062(2) Uani 1 1 d . . .
H32A H 0.2259 0.3789 0.3154 0.074 Uiso 1 1 calc R . .
C33 C 0.2231(4) 0.3747(6) 0.2084(4) 0.0488(18) Uani 1 1 d . . .
C34 C 0.1649(4) 0.4555(6) 0.2008(4) 0.0453(18) Uani 1 1 d . . .
C35 C 0.1108(5) 0.4785(8) 0.2511(5) 0.062(2) Uani 1 1 d . . .
H35A H 0.1059 0.4436 0.2942 0.074 Uiso 1 1 calc R . .
C36 C 0.0677(4) 0.5606(8) 0.2250(5) 0.065(2) Uani 1 1 d . . .
H36A H 0.0261 0.5882 0.2455 0.079 Uiso 1 1 calc R . .
C37 C 0.0968(4) 0.5955(6) 0.1629(4) 0.0468(17) Uani 1 1 d . . .
C38 C 0.0780(4) 0.6810(6) 0.1144(4) 0.0508(19) Uani 1 1 d . . .
C39 C 0.0203(5) 0.7545(8) 0.1198(5) 0.077(3) Uani 1 1 d . . .
H39A H -0.0107 0.7472 0.1573 0.092 Uiso 1 1 calc R . .
C40 C 0.0085(5) 0.8312(9) 0.0754(7) 0.091(4) Uani 1 1 d . . .
H40A H -0.0290 0.8816 0.0821 0.110 Uiso 1 1 calc R . .
C41 C 0.0529(5) 0.8400(8) 0.0152(6) 0.086(3) Uani 1 1 d . . .
H41A H 0.0438 0.8925 -0.0196 0.103 Uiso 1 1 calc R . .
C42 C 0.1091(5) 0.7677(6) 0.0114(5) 0.066(2) Uani 1 1 d . . .
H42A H 0.1400 0.7735 -0.0264 0.079 Uiso 1 1 calc R . .
S1 S 0.45978(13) -0.0639(2) 0.29447(15) 0.0711(7) Uani 1 1 d . . .
F1 F 0.5288(4) 0.0325(5) 0.3981(3) 0.100(2) Uani 1 1 d . . .
F2 F 0.5442(5) 0.1108(9) 0.3032(5) 0.184(5) Uani 1 1 d . . .
F3 F 0.4460(4) 0.1306(5) 0.3525(4) 0.120(3) Uani 1 1 d . . .
O1 O 0.4062(6) -0.0984(8) 0.3396(7) 0.158(4) Uani 1 1 d . . .
O2 O 0.4364(5) -0.0190(8) 0.2332(6) 0.151(5) Uani 1 1 d . . .
O3 O 0.5191(4) -0.1439(6) 0.2906(4) 0.099(3) Uani 1 1 d . . .
C43 C 0.4942(6) 0.0582(8) 0.3395(6) 0.075(3) 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 N8 1.950(6) . ?
Cu1 N4 1.988(6) . ?
Cu1 N3 2.066(5) . ?
Cu1 N9 2.094(5) . ?
Cu1 N5 2.341(5) . ?
Cu1 Cu2 2.8147(10) . ?
Cu2 N2 1.954(5) . ?
Cu2 N6 1.982(5) . ?
Cu2 N7 2.051(6) . ?
Cu2 N5 2.155(5) . ?
Cu2 N1 2.199(6) . ?
N1 C1 1.314(9) . ?
N1 C5 1.336(9) . ?
N2 C6 1.324(8) . ?
N2 C9 1.372(8) . ?
N3 C10 1.306(9) . ?
N3 C14 1.335(9) . ?
N4 C19 1.334(9) . ?
N4 C15 1.359(8) . ?
N5 C23 1.366(8) . ?
N5 C20 1.381(8) . ?
N6 C28 1.325(9) . ?
N6 C24 1.338(9) . ?
N7 C33 1.333(10) . ?
N7 C29 1.359(9) . ?
N8 C34 1.337(9) . ?
N8 C37 1.410(9) . ?
N9 C42 1.308(10) . ?
N9 C38 1.368(10) . ?
C1 C2 1.367(12) . ?
C1 H1A 0.9300 . ?
C2 C3 1.369(15) . ?
C2 H2A 0.9300 . ?
C3 C4 1.514(15) . ?
C3 H3A 0.9300 . ?
C4 C5 1.385(10) . ?
C4 H4A 0.9300 . ?
C5 C6 1.466(9) . ?
C6 C7 1.391(10) . ?
C7 C8 1.419(12) . ?
C7 H7A 0.9300 . ?
C8 C9 1.418(10) . ?
C8 H8A 0.9300 . ?
C9 C10 1.445(9) . ?
C10 C11 1.464(10) . ?
C11 C12 1.388(12) . ?
C11 H11A 0.9300 . ?
C12 C13 1.338(12) . ?
C12 H12A 0.9300 . ?
C13 C14 1.415(10) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 C16 1.331(11) . ?
C15 H15A 0.9300 . ?
C16 C17 1.339(12) . ?
C16 H16A 0.9300 . ?
C17 C18 1.423(12) . ?
C17 H17A 0.9300 . ?
C18 C19 1.364(11) . ?
C18 H18A 0.9300 . ?
C19 C20 1.464(10) . ?
C20 C21 1.341(11) . ?
C21 C22 1.386(12) . ?
C21 H21A 0.9300 . ?
C22 C23 1.352(10) . ?
C22 H22A 0.9300 . ?
C23 C24 1.447(10) . ?
C24 C25 1.427(9) . ?
C25 C26 1.352(13) . ?
C25 H25A 0.9300 . ?
C26 C27 1.353(13) . ?
C26 H26A 0.9300 . ?
C27 C28 1.366(11) . ?
C27 H27A 0.9300 . ?
C28 H28A 0.9300 . ?
C29 C30 1.394(11) . ?
C29 H29A 0.9300 . ?
C30 C31 1.311(12) . ?
C30 H30A 0.9300 . ?
C31 C32 1.391(12) . ?
C31 H31A 0.9300 . ?
C32 C33 1.418(10) . ?
C32 H32A 0.9300 . ?
C33 C34 1.456(11) . ?
C34 C35 1.426(11) . ?
C35 C36 1.360(12) . ?
C35 H35A 0.9300 . ?
C36 C37 1.376(11) . ?
C36 H36A 0.9300 . ?
C37 C38 1.423(11) . ?
C38 C39 1.389(11) . ?
C39 C40 1.267(14) . ?
C39 H39A 0.9300 . ?
C40 C41 1.428(15) . ?
C40 H40A 0.9300 . ?
C41 C42 1.358(12) . ?
C41 H41A 0.9300 . ?
C42 H42A 0.9300 . ?
S1 O2 1.366(10) . ?
S1 O1 1.385(10) . ?
S1 O3 1.461(7) . ?
S1 C43 1.807(10) . ?
F1 C43 1.335(11) . ?
F2 C43 1.321(12) . ?
F3 C43 1.269(12) . ?

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
N8 Cu1 N4 176.1(2) . . ?
N8 Cu1 N3 93.9(2) . . ?
N4 Cu1 N3 89.9(2) . . ?
N8 Cu1 N9 82.8(3) . . ?
N4 Cu1 N9 93.9(2) . . ?
N3 Cu1 N9 133.5(2) . . ?
N8 Cu1 N5 98.2(2) . . ?
N4 Cu1 N5 79.8(2) . . ?
N3 Cu1 N5 131.2(2) . . ?
N9 Cu1 N5 94.9(2) . . ?
N8 Cu1 Cu2 79.49(17) . . ?
N4 Cu1 Cu2 101.50(16) . . ?
N3 Cu1 Cu2 88.61(15) . . ?
N9 Cu1 Cu2 135.33(14) . . ?
N5 Cu1 Cu2 48.35(12) . . ?
N2 Cu2 N6 170.8(2) . . ?
N2 Cu2 N7 93.2(2) . . ?
N6 Cu2 N7 93.6(2) . . ?
N2 Cu2 N5 97.6(2) . . ?
N6 Cu2 N5 81.0(2) . . ?
N7 Cu2 N5 139.7(2) . . ?
N2 Cu2 N1 80.7(2) . . ?
N6 Cu2 N1 90.4(2) . . ?
N7 Cu2 N1 123.3(2) . . ?
N5 Cu2 N1 96.8(2) . . ?
N2 Cu2 Cu1 81.68(16) . . ?
N6 Cu2 Cu1 104.47(14) . . ?
N7 Cu2 Cu1 89.57(16) . . ?
N5 Cu2 Cu1 54.26(14) . . ?
N1 Cu2 Cu1 143.30(16) . . ?
C1 N1 C5 121.0(7) . . ?
C1 N1 Cu2 129.6(6) . . ?
C5 N1 Cu2 109.3(4) . . ?
C6 N2 C9 107.5(5) . . ?
C6 N2 Cu2 114.7(4) . . ?
C9 N2 Cu2 137.0(5) . . ?
C10 N3 C14 121.3(6) . . ?
C10 N3 Cu1 128.1(5) . . ?
C14 N3 Cu1 110.3(5) . . ?
C19 N4 C15 118.7(6) . . ?
C19 N4 Cu1 117.1(4) . . ?
C15 N4 Cu1 124.0(5) . . ?
C23 N5 C20 105.2(5) . . ?
C23 N5 Cu2 104.3(4) . . ?
C20 N5 Cu2 135.2(4) . . ?
C23 N5 Cu1 139.4(4) . . ?
C20 N5 Cu1 100.3(4) . . ?
Cu2 N5 Cu1 77.39(17) . . ?
C28 N6 C24 118.4(6) . . ?
C28 N6 Cu2 127.3(5) . . ?
C24 N6 Cu2 113.7(4) . . ?
C33 N7 C29 121.8(6) . . ?
C33 N7 Cu2 127.3(5) . . ?
C29 N7 Cu2 110.5(5) . . ?
C34 N8 C37 107.6(6) . . ?
C34 N8 Cu1 138.2(5) . . ?
C37 N8 Cu1 111.8(5) . . ?
C42 N9 C38 119.2(6) . . ?
C42 N9 Cu1 130.0(6) . . ?
C38 N9 Cu1 110.6(5) . . ?
N1 C1 C2 124.3(9) . . ?
N1 C1 H1A 117.8 . . ?
C2 C1 H1A 117.8 . . ?
C1 C2 C3 115.1(9) . . ?
C1 C2 H2A 122.4 . . ?
C3 C2 H2A 122.4 . . ?
C2 C3 C4 123.1(9) . . ?
C2 C3 H3A 118.5 . . ?
C4 C3 H3A 118.5 . . ?
C5 C4 C3 111.8(8) . . ?
C5 C4 H4A 124.1 . . ?
C3 C4 H4A 124.1 . . ?
N1 C5 C4 123.6(7) . . ?
N1 C5 C6 114.7(6) . . ?
C4 C5 C6 121.7(8) . . ?
N2 C6 C7 112.7(7) . . ?
N2 C6 C5 120.4(6) . . ?
C7 C6 C5 126.7(7) . . ?
C6 C7 C8 104.4(7) . . ?
C6 C7 H7A 127.8 . . ?
C8 C7 H7A 127.8 . . ?
C9 C8 C7 106.7(7) . . ?
C9 C8 H8A 126.7 . . ?
C7 C8 H8A 126.7 . . ?
N2 C9 C8 108.5(6) . . ?
N2 C9 C10 124.2(6) . . ?
C8 C9 C10 127.1(7) . . ?
N3 C10 C9 122.7(6) . . ?
N3 C10 C11 118.6(7) . . ?
C9 C10 C11 118.4(7) . . ?
C12 C11 C10 119.3(7) . . ?
C12 C11 H11A 120.4 . . ?
C10 C11 H11A 120.4 . . ?
C13 C12 C11 119.5(8) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
C12 C13 C14 119.0(8) . . ?
C12 C13 H13A 120.5 . . ?
C14 C13 H13A 120.5 . . ?
N3 C14 C13 121.9(7) . . ?
N3 C14 H14A 119.1 . . ?
C13 C14 H14A 119.1 . . ?
C16 C15 N4 123.5(8) . . ?
C16 C15 H15A 118.2 . . ?
N4 C15 H15A 118.2 . . ?
C15 C16 C17 119.0(7) . . ?
C15 C16 H16A 120.5 . . ?
C17 C16 H16A 120.5 . . ?
C16 C17 C18 119.1(7) . . ?
C16 C17 H17A 120.5 . . ?
C18 C17 H17A 120.5 . . ?
C19 C18 C17 119.0(8) . . ?
C19 C18 H18A 120.5 . . ?
C17 C18 H18A 120.5 . . ?
N4 C19 C18 120.5(7) . . ?
N4 C19 C20 116.1(6) . . ?
C18 C19 C20 123.4(7) . . ?
C21 C20 N5 109.8(6) . . ?
C21 C20 C19 128.4(7) . . ?
N5 C20 C19 121.0(6) . . ?
C20 C21 C22 107.8(7) . . ?
C20 C21 H21A 126.1 . . ?
C22 C21 H21A 126.1 . . ?
C23 C22 C21 106.5(7) . . ?
C23 C22 H22A 126.7 . . ?
C21 C22 H22A 126.7 . . ?
C22 C23 N5 110.5(6) . . ?
C22 C23 C24 131.2(7) . . ?
N5 C23 C24 118.0(6) . . ?
N6 C24 C25 121.5(7) . . ?
N6 C24 C23 115.9(6) . . ?
C25 C24 C23 122.3(7) . . ?
C26 C25 C24 118.1(8) . . ?
C26 C25 H25A 121.0 . . ?
C24 C25 H25A 121.0 . . ?
C25 C26 C27 118.8(7) . . ?
C25 C26 H26A 120.6 . . ?
C27 C26 H26A 120.6 . . ?
C26 C27 C28 121.4(8) . . ?
C26 C27 H27A 119.3 . . ?
C28 C27 H27A 119.3 . . ?
N6 C28 C27 121.6(8) . . ?
N6 C28 H28A 119.2 . . ?
C27 C28 H28A 119.2 . . ?
N7 C29 C30 118.3(8) . . ?
N7 C29 H29A 120.9 . . ?
C30 C29 H29A 120.9 . . ?
C31 C30 C29 121.5(9) . . ?
C31 C30 H30A 119.3 . . ?
C29 C30 H30A 119.3 . . ?
C30 C31 C32 120.9(7) . . ?
C30 C31 H31A 119.6 . . ?
C32 C31 H31A 119.6 . . ?
C31 C32 C33 117.4(8) . . ?
C31 C32 H32A 121.3 . . ?
C33 C32 H32A 121.3 . . ?
N7 C33 C32 119.9(7) . . ?
N7 C33 C34 121.2(7) . . ?
C32 C33 C34 118.6(8) . . ?
N8 C34 C35 108.2(7) . . ?
N8 C34 C33 125.8(7) . . ?
C35 C34 C33 125.9(7) . . ?
C36 C35 C34 107.8(8) . . ?
C36 C35 H35A 126.1 . . ?
C34 C35 H35A 126.1 . . ?
C35 C36 C37 107.7(7) . . ?
C35 C36 H36A 126.2 . . ?
C37 C36 H36A 126.2 . . ?
C36 C37 N8 108.3(7) . . ?
C36 C37 C38 133.4(7) . . ?
N8 C37 C38 118.2(7) . . ?
N9 C38 C39 118.4(8) . . ?
N9 C38 C37 115.4(6) . . ?
C39 C38 C37 126.3(8) . . ?
C40 C39 C38 122.4(10) . . ?
C40 C39 H39A 118.8 . . ?
C38 C39 H39A 118.8 . . ?
C39 C40 C41 119.9(8) . . ?
C39 C40 H40A 120.0 . . ?
C41 C40 H40A 120.0 . . ?
C42 C41 C40 116.4(9) . . ?
C42 C41 H41A 121.8 . . ?
C40 C41 H41A 121.8 . . ?
N9 C42 C41 123.5(10) . . ?
N9 C42 H42A 118.2 . . ?
C41 C42 H42A 118.2 . . ?
O2 S1 O1 115.2(8) . . ?
O2 S1 O3 116.9(6) . . ?
O1 S1 O3 112.7(7) . . ?
O2 S1 C43 102.3(5) . . ?
O1 S1 C43 101.2(6) . . ?
O3 S1 C43 106.1(5) . . ?
F3 C43 F2 106.5(10) . . ?
F3 C43 F1 109.3(9) . . ?
F2 C43 F1 102.3(8) . . ?
F3 C43 S1 112.7(7) . . ?
F2 C43 S1 112.2(9) . . ?
F1 C43 S1 113.1(7) . . ?

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
N8 Cu1 Cu2 N2 -143.2(2) . . . . ?
N4 Cu1 Cu2 N2 40.7(2) . . . . ?
N3 Cu1 Cu2 N2 -49.0(2) . . . . ?
N9 Cu1 Cu2 N2 148.4(3) . . . . ?
N5 Cu1 Cu2 N2 105.7(2) . . . . ?
N8 Cu1 Cu2 N6 43.8(2) . . . . ?
N4 Cu1 Cu2 N6 -132.4(2) . . . . ?
N3 Cu1 Cu2 N6 138.0(2) . . . . ?
N9 Cu1 Cu2 N6 -24.7(3) . . . . ?
N5 Cu1 Cu2 N6 -67.3(2) . . . . ?
N8 Cu1 Cu2 N7 -49.9(2) . . . . ?
N4 Cu1 Cu2 N7 134.0(2) . . . . ?
N3 Cu1 Cu2 N7 44.3(2) . . . . ?
N9 Cu1 Cu2 N7 -118.3(3) . . . . ?
N5 Cu1 Cu2 N7 -161.0(2) . . . . ?
N8 Cu1 Cu2 N5 111.1(2) . . . . ?
N4 Cu1 Cu2 N5 -65.1(2) . . . . ?
N3 Cu1 Cu2 N5 -154.7(2) . . . . ?
N9 Cu1 Cu2 N5 42.7(3) . . . . ?
N8 Cu1 Cu2 N1 154.8(3) . . . . ?
N4 Cu1 Cu2 N1 -21.3(3) . . . . ?
N3 Cu1 Cu2 N1 -111.0(3) . . . . ?
N9 Cu1 Cu2 N1 86.4(4) . . . . ?
N5 Cu1 Cu2 N1 43.7(3) . . . . ?
N2 Cu2 N1 C1 179.3(7) . . . . ?
N6 Cu2 N1 C1 -3.1(6) . . . . ?
N7 Cu2 N1 C1 91.5(7) . . . . ?
N5 Cu2 N1 C1 -84.0(6) . . . . ?
Cu1 Cu2 N1 C1 -118.4(6) . . . . ?
N2 Cu2 N1 C5 -3.0(4) . . . . ?
N6 Cu2 N1 C5 174.6(5) . . . . ?
N7 Cu2 N1 C5 -90.7(5) . . . . ?
N5 Cu2 N1 C5 93.7(4) . . . . ?
Cu1 Cu2 N1 C5 59.3(5) . . . . ?
N6 Cu2 N2 C6 -13.0(17) . . . . ?
N7 Cu2 N2 C6 125.2(5) . . . . ?
N5 Cu2 N2 C6 -93.6(5) . . . . ?
N1 Cu2 N2 C6 2.0(5) . . . . ?
Cu1 Cu2 N2 C6 -145.7(5) . . . . ?
N6 Cu2 N2 C9 178.8(12) . . . . ?
N7 Cu2 N2 C9 -43.0(6) . . . . ?
N5 Cu2 N2 C9 98.2(6) . . . . ?
N1 Cu2 N2 C9 -166.2(7) . . . . ?
Cu1 Cu2 N2 C9 46.1(6) . . . . ?
N8 Cu1 N3 C10 128.9(6) . . . . ?
N4 Cu1 N3 C10 -52.0(6) . . . . ?
N9 Cu1 N3 C10 -147.3(5) . . . . ?
N5 Cu1 N3 C10 24.4(7) . . . . ?
Cu2 Cu1 N3 C10 49.5(5) . . . . ?
N8 Cu1 N3 C14 -57.2(5) . . . . ?
N4 Cu1 N3 C14 122.0(5) . . . . ?
N9 Cu1 N3 C14 26.7(6) . . . . ?
N5 Cu1 N3 C14 -161.6(4) . . . . ?
Cu2 Cu1 N3 C14 -136.5(5) . . . . ?
N8 Cu1 N4 C19 -49(4) . . . . ?
N3 Cu1 N4 C19 143.8(5) . . . . ?
N9 Cu1 N4 C19 -82.6(5) . . . . ?
N5 Cu1 N4 C19 11.7(5) . . . . ?
Cu2 Cu1 N4 C19 55.2(5) . . . . ?
N8 Cu1 N4 C15 126(3) . . . . ?
N3 Cu1 N4 C15 -40.8(5) . . . . ?
N9 Cu1 N4 C15 92.8(5) . . . . ?
N5 Cu1 N4 C15 -172.9(5) . . . . ?
Cu2 Cu1 N4 C15 -129.4(5) . . . . ?
N2 Cu2 N5 C23 147.8(4) . . . . ?
N6 Cu2 N5 C23 -23.0(4) . . . . ?
N7 Cu2 N5 C23 -108.0(5) . . . . ?
N1 Cu2 N5 C23 66.3(4) . . . . ?
Cu1 Cu2 N5 C23 -138.3(4) . . . . ?
N2 Cu2 N5 C20 18.0(6) . . . . ?
N6 Cu2 N5 C20 -152.8(6) . . . . ?
N7 Cu2 N5 C20 122.3(6) . . . . ?
N1 Cu2 N5 C20 -63.5(6) . . . . ?
Cu1 Cu2 N5 C20 92.0(6) . . . . ?
N2 Cu2 N5 Cu1 -74.0(2) . . . . ?
N6 Cu2 N5 Cu1 115.23(19) . . . . ?
N7 Cu2 N5 Cu1 30.3(4) . . . . ?
N1 Cu2 N5 Cu1 -155.43(18) . . . . ?
N8 Cu1 N5 C23 29.4(7) . . . . ?
N4 Cu1 N5 C23 -147.1(7) . . . . ?
N3 Cu1 N5 C23 132.0(6) . . . . ?
N9 Cu1 N5 C23 -54.1(7) . . . . ?
Cu2 Cu1 N5 C23 97.4(7) . . . . ?
N8 Cu1 N5 C20 157.8(4) . . . . ?
N4 Cu1 N5 C20 -18.8(4) . . . . ?
N3 Cu1 N5 C20 -99.7(4) . . . . ?
N9 Cu1 N5 C20 74.3(4) . . . . ?
Cu2 Cu1 N5 C20 -134.3(4) . . . . ?
N8 Cu1 N5 Cu2 -68.0(2) . . . . ?
N4 Cu1 N5 Cu2 115.5(2) . . . . ?
N3 Cu1 N5 Cu2 34.6(3) . . . . ?
N9 Cu1 N5 Cu2 -151.4(2) . . . . ?
N2 Cu2 N6 C28 105.9(15) . . . . ?
N7 Cu2 N6 C28 -32.4(6) . . . . ?
N5 Cu2 N6 C28 -172.2(6) . . . . ?
N1 Cu2 N6 C28 91.0(6) . . . . ?
Cu1 Cu2 N6 C28 -122.9(5) . . . . ?
N2 Cu2 N6 C24 -64.3(15) . . . . ?
N7 Cu2 N6 C24 157.5(5) . . . . ?
N5 Cu2 N6 C24 17.7(5) . . . . ?
N1 Cu2 N6 C24 -79.1(5) . . . . ?
Cu1 Cu2 N6 C24 67.0(5) . . . . ?
N2 Cu2 N7 C33 133.1(6) . . . . ?
N6 Cu2 N7 C33 -53.0(6) . . . . ?
N5 Cu2 N7 C33 27.3(8) . . . . ?
N1 Cu2 N7 C33 -145.9(6) . . . . ?
Cu1 Cu2 N7 C33 51.5(6) . . . . ?
N2 Cu2 N7 C29 -54.5(5) . . . . ?
N6 Cu2 N7 C29 119.3(5) . . . . ?
N5 Cu2 N7 C29 -160.4(4) . . . . ?
N1 Cu2 N7 C29 26.5(6) . . . . ?
Cu1 Cu2 N7 C29 -136.2(5) . . . . ?
N4 Cu1 N8 C34 157(3) . . . . ?
N3 Cu1 N8 C34 -35.4(7) . . . . ?
N9 Cu1 N8 C34 -168.8(7) . . . . ?
N5 Cu1 N8 C34 97.2(7) . . . . ?
Cu2 Cu1 N8 C34 52.4(6) . . . . ?
N4 Cu1 N8 C37 -44(4) . . . . ?
N3 Cu1 N8 C37 123.6(4) . . . . ?
N9 Cu1 N8 C37 -9.7(4) . . . . ?
N5 Cu1 N8 C37 -103.7(4) . . . . ?
Cu2 Cu1 N8 C37 -148.5(4) . . . . ?
N8 Cu1 N9 C42 -177.5(7) . . . . ?
N4 Cu1 N9 C42 0.3(7) . . . . ?
N3 Cu1 N9 C42 93.9(7) . . . . ?
N5 Cu1 N9 C42 -79.8(7) . . . . ?
Cu2 Cu1 N9 C42 -110.3(6) . . . . ?
N8 Cu1 N9 C38 7.5(5) . . . . ?
N4 Cu1 N9 C38 -174.7(5) . . . . ?
N3 Cu1 N9 C38 -81.1(5) . . . . ?
N5 Cu1 N9 C38 105.2(5) . . . . ?
Cu2 Cu1 N9 C38 74.7(5) . . . . ?
C5 N1 C1 C2 9.1(12) . . . . ?
Cu2 N1 C1 C2 -173.4(7) . . . . ?
N1 C1 C2 C3 -12.2(15) . . . . ?
C1 C2 C3 C4 6.7(15) . . . . ?
C2 C3 C4 C5 1.2(14) . . . . ?
C1 N1 C5 C4 0.4(11) . . . . ?
Cu2 N1 C5 C4 -177.5(6) . . . . ?
C1 N1 C5 C6 -178.7(6) . . . . ?
Cu2 N1 C5 C6 3.3(7) . . . . ?
C3 C4 C5 N1 -5.0(11) . . . . ?
C3 C4 C5 C6 174.1(7) . . . . ?
C9 N2 C6 C7 -4.4(8) . . . . ?
Cu2 N2 C6 C7 -176.0(5) . . . . ?
C9 N2 C6 C5 170.8(6) . . . . ?
Cu2 N2 C6 C5 -0.8(8) . . . . ?
N1 C5 C6 N2 -2.0(9) . . . . ?
C4 C5 C6 N2 178.8(7) . . . . ?
N1 C5 C6 C7 172.5(7) . . . . ?
C4 C5 C6 C7 -6.7(12) . . . . ?
N2 C6 C7 C8 5.1(9) . . . . ?
C5 C6 C7 C8 -169.8(7) . . . . ?
C6 C7 C8 C9 -3.6(8) . . . . ?
C6 N2 C9 C8 1.8(7) . . . . ?
Cu2 N2 C9 C8 170.6(5) . . . . ?
C6 N2 C9 C10 -173.0(6) . . . . ?
Cu2 N2 C9 C10 -4.2(10) . . . . ?
C7 C8 C9 N2 1.2(8) . . . . ?
C7 C8 C9 C10 175.8(6) . . . . ?
C14 N3 C10 C9 178.0(6) . . . . ?
Cu1 N3 C10 C9 -8.6(9) . . . . ?
C14 N3 C10 C11 -7.6(9) . . . . ?
Cu1 N3 C10 C11 165.8(5) . . . . ?
N2 C9 C10 N3 -32.1(9) . . . . ?
C8 C9 C10 N3 154.1(7) . . . . ?
N2 C9 C10 C11 153.5(6) . . . . ?
C8 C9 C10 C11 -20.3(10) . . . . ?
N3 C10 C11 C12 3.2(10) . . . . ?
C9 C10 C11 C12 177.9(7) . . . . ?
C10 C11 C12 C13 2.5(11) . . . . ?
C11 C12 C13 C14 -3.8(11) . . . . ?
C10 N3 C14 C13 6.5(11) . . . . ?
Cu1 N3 C14 C13 -168.0(6) . . . . ?
C12 C13 C14 N3 -0.5(11) . . . . ?
C19 N4 C15 C16 2.0(11) . . . . ?
Cu1 N4 C15 C16 -173.3(6) . . . . ?
N4 C15 C16 C17 -5.6(12) . . . . ?
C15 C16 C17 C18 4.3(13) . . . . ?
C16 C17 C18 C19 0.1(13) . . . . ?
C15 N4 C19 C18 2.6(11) . . . . ?
Cu1 N4 C19 C18 178.3(6) . . . . ?
C15 N4 C19 C20 -177.5(6) . . . . ?
Cu1 N4 C19 C20 -1.8(8) . . . . ?
C17 C18 C19 N4 -3.6(12) . . . . ?
C17 C18 C19 C20 176.5(7) . . . . ?
C23 N5 C20 C21 2.1(8) . . . . ?
Cu2 N5 C20 C21 131.6(7) . . . . ?
Cu1 N5 C20 C21 -146.0(6) . . . . ?
C23 N5 C20 C19 173.1(6) . . . . ?
Cu2 N5 C20 C19 -57.4(9) . . . . ?
Cu1 N5 C20 C19 25.0(7) . . . . ?
N4 C19 C20 C21 150.0(8) . . . . ?
C18 C19 C20 C21 -30.2(13) . . . . ?
N4 C19 C20 N5 -19.2(10) . . . . ?
C18 C19 C20 N5 160.7(7) . . . . ?
N5 C20 C21 C22 0.2(10) . . . . ?
C19 C20 C21 C22 -169.9(8) . . . . ?
C20 C21 C22 C23 -2.4(10) . . . . ?
C21 C22 C23 N5 3.8(9) . . . . ?
C21 C22 C23 C24 -170.9(8) . . . . ?
C20 N5 C23 C22 -3.6(7) . . . . ?
Cu2 N5 C23 C22 -149.5(5) . . . . ?
Cu1 N5 C23 C22 123.3(7) . . . . ?
C20 N5 C23 C24 171.8(6) . . . . ?
Cu2 N5 C23 C24 26.0(6) . . . . ?
Cu1 N5 C23 C24 -61.3(8) . . . . ?
C28 N6 C24 C25 -6.1(10) . . . . ?
Cu2 N6 C24 C25 165.0(5) . . . . ?
C28 N6 C24 C23 -179.7(6) . . . . ?
Cu2 N6 C24 C23 -8.7(8) . . . . ?
C22 C23 C24 N6 160.5(7) . . . . ?
N5 C23 C24 N6 -13.9(9) . . . . ?
C22 C23 C24 C25 -13.1(12) . . . . ?
N5 C23 C24 C25 172.5(6) . . . . ?
N6 C24 C25 C26 6.2(11) . . . . ?
C23 C24 C25 C26 179.5(7) . . . . ?
C24 C25 C26 C27 -3.1(12) . . . . ?
C25 C26 C27 C28 0.1(13) . . . . ?
C24 N6 C28 C27 2.9(11) . . . . ?
Cu2 N6 C28 C27 -166.8(6) . . . . ?
C26 C27 C28 N6 0.1(13) . . . . ?
C33 N7 C29 C30 0.5(11) . . . . ?
Cu2 N7 C29 C30 -172.4(5) . . . . ?
N7 C29 C30 C31 2.5(12) . . . . ?
C29 C30 C31 C32 -6.3(13) . . . . ?
C30 C31 C32 C33 6.9(12) . . . . ?
C29 N7 C33 C32 0.4(11) . . . . ?
Cu2 N7 C33 C32 172.0(5) . . . . ?
C29 N7 C33 C34 174.4(6) . . . . ?
Cu2 N7 C33 C34 -14.0(10) . . . . ?
C31 C32 C33 N7 -4.0(11) . . . . ?
C31 C32 C33 C34 -178.1(7) . . . . ?
C37 N8 C34 C35 3.2(7) . . . . ?
Cu1 N8 C34 C35 162.8(6) . . . . ?
C37 N8 C34 C33 -174.4(7) . . . . ?
Cu1 N8 C34 C33 -14.8(11) . . . . ?
N7 C33 C34 N8 -23.3(11) . . . . ?
C32 C33 C34 N8 150.8(7) . . . . ?
N7 C33 C34 C35 159.6(7) . . . . ?
C32 C33 C34 C35 -26.3(11) . . . . ?
N8 C34 C35 C36 1.0(9) . . . . ?
C33 C34 C35 C36 178.6(7) . . . . ?
C34 C35 C36 C37 -4.9(10) . . . . ?
C35 C36 C37 N8 6.9(9) . . . . ?
C35 C36 C37 C38 -176.6(8) . . . . ?
C34 N8 C37 C36 -6.3(7) . . . . ?
Cu1 N8 C37 C36 -171.8(5) . . . . ?
C34 N8 C37 C38 176.6(6) . . . . ?
Cu1 N8 C37 C38 11.0(8) . . . . ?
C42 N9 C38 C39 0.1(11) . . . . ?
Cu1 N9 C38 C39 175.8(6) . . . . ?
C42 N9 C38 C37 -179.2(7) . . . . ?
Cu1 N9 C38 C37 -3.6(7) . . . . ?
C36 C37 C38 N9 179.0(8) . . . . ?
N8 C37 C38 N9 -4.7(9) . . . . ?
C36 C37 C38 C39 -0.3(14) . . . . ?
N8 C37 C38 C39 176.0(8) . . . . ?
N9 C38 C39 C40 -1.8(14) . . . . ?
C37 C38 C39 C40 177.5(9) . . . . ?
C38 C39 C40 C41 3.7(16) . . . . ?
C39 C40 C41 C42 -3.9(15) . . . . ?
C38 N9 C42 C41 -0.6(12) . . . . ?
Cu1 N9 C42 C41 -175.2(7) . . . . ?
C40 C41 C42 N9 2.4(14) . . . . ?
O2 S1 C43 F3 63.4(10) . . . . ?
O1 S1 C43 F3 -55.7(10) . . . . ?
O3 S1 C43 F3 -173.5(8) . . . . ?
O2 S1 C43 F2 -56.8(10) . . . . ?
O1 S1 C43 F2 -175.9(10) . . . . ?
O3 S1 C43 F2 66.2(9) . . . . ?
O2 S1 C43 F1 -171.9(9) . . . . ?
O1 S1 C43 F1 68.9(10) . . . . ?
O3 S1 C43 F1 -48.9(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.102

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.250 -0.040 0.148 136 66 ' '
2 0.250 -0.040 0.648 136 66 ' '
3 0.750 0.039 0.148 136 66 ' '
4 0.750 0.039 0.648 136 66 ' '
_platon_squeeze_details          
;
;
