# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_exp_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24 Cu F6 N12 O6 S4'
_chemical_formula_weight         930.37

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'
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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   9.2150(3)
_cell_length_b                   18.8491(5)
_cell_length_c                   10.4290(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.392(3)
_cell_angle_gamma                90.00
_cell_volume                     1781.75(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    284(2)
_cell_measurement_reflns_used    3403
_cell_measurement_theta_min      2.7117
_cell_measurement_theta_max      28.4418

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             942
_exptl_absorpt_coefficient_mu    0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7591
_exptl_absorpt_correction_T_max  0.9285
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      284(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  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         13031
_diffrn_standards_interval_count 0.3
_diffrn_standards_interval_time  5
_diffrn_standards_decay_%        none
_diffrn_reflns_number            11284
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3318
_reflns_number_gt                2740
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0263P)^2^+1.2221P] where P=(Fo^2^+2Fc^2^)/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         3318
_refine_ls_number_parameters     259
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0781
_refine_ls_wR_factor_gt          0.0725
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.053
_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
C1 C 0.6785(3) -0.11414(14) 0.3256(3) 0.0426(7) Uani 1 1 d . . .
H1 H 0.6007 -0.1456 0.3257 0.051 Uiso 1 1 calc R . .
C2 C 0.7970(4) -0.13581(15) 0.2704(3) 0.0472(8) Uani 1 1 d . . .
H2 H 0.7982 -0.1809 0.2343 0.057 Uiso 1 1 calc R . .
C3 C 0.9123(3) -0.09019(15) 0.2695(3) 0.0433(7) Uani 1 1 d . . .
H3 H 0.9927 -0.1038 0.2327 0.052 Uiso 1 1 calc R . .
C4 C 0.9076(3) -0.02329(14) 0.3242(2) 0.0352(6) Uani 1 1 d . . .
H4 H 0.9847 0.0086 0.3252 0.042 Uiso 1 1 calc R . .
C5 C 0.7858(3) -0.00523(12) 0.3773(2) 0.0261(5) Uani 1 1 d . . .
C6 C 0.7640(3) 0.06304(12) 0.4386(2) 0.0237(5) Uani 1 1 d . . .
C7 C 0.7743(3) 0.17080(12) 0.5156(2) 0.0263(5) Uani 1 1 d . . .
C8 C 0.7435(3) 0.27959(13) 0.6805(3) 0.0382(6) Uani 1 1 d . . .
H8A H 0.6403 0.2668 0.6557 0.046 Uiso 1 1 calc R . .
H8B H 0.7841 0.2546 0.7602 0.046 Uiso 1 1 calc R . .
C9 C 0.7584(3) 0.35849(13) 0.7015(2) 0.0314(6) Uani 1 1 d . . .
C10 C 0.6815(3) 0.40526(14) 0.6117(3) 0.0403(7) Uani 1 1 d . . .
H10 H 0.6180 0.3883 0.5386 0.048 Uiso 1 1 calc R . .
C11 C 0.6998(3) 0.47695(15) 0.6315(3) 0.0439(7) Uani 1 1 d . . .
H11 H 0.6489 0.5090 0.5721 0.053 Uiso 1 1 calc R . .
C12 C 0.7944(3) 0.50086(13) 0.7402(3) 0.0361(6) Uani 1 1 d . . .
H12 H 0.8086 0.5495 0.7514 0.043 Uiso 1 1 calc R . .
C13 C 0.8473(3) 0.38704(12) 0.8103(2) 0.0297(6) Uani 1 1 d . . .
H13 H 0.8963 0.3561 0.8729 0.036 Uiso 1 1 calc R . .
C14 C 0.1659(4) 0.37390(18) 0.5728(3) 0.0574(9) Uani 1 1 d . . .
Cu1 Cu 0.5000 0.0000 0.5000 0.02275(12) Uani 1 2 d SU . .
F1 F 0.2387(3) 0.43340(11) 0.6109(2) 0.0861(7) Uani 1 1 d . . .
F2 F 0.0562(3) 0.38947(13) 0.4769(2) 0.0915(7) Uani 1 1 d . . .
F3 F 0.1062(2) 0.35197(13) 0.6731(2) 0.0836(7) Uani 1 1 d . . .
N1 N 0.6710(2) -0.05031(10) 0.37840(19) 0.0302(5) Uani 1 1 d U . .
N2 N 0.8667(2) 0.45687(10) 0.83029(19) 0.0285(5) Uani 1 1 d . . .
N3 N 0.6495(2) 0.07460(9) 0.49525(18) 0.0236(4) Uani 1 1 d . . .
N4 N 0.8459(2) 0.12347(10) 0.44900(18) 0.0251(4) Uani 1 1 d . . .
N5 N 0.6544(2) 0.14236(10) 0.54545(19) 0.0287(5) Uani 1 1 d . . .
N6 N 0.9785(2) 0.13322(11) 0.4012(2) 0.0344(5) Uani 1 1 d . . .
H6B H 0.9598 0.1579 0.3283 0.041 Uiso 1 1 d R . .
H6A H 1.0393 0.1586 0.4571 0.041 Uiso 1 1 d R . .
O1 O 0.3575(3) 0.34344(12) 0.4321(2) 0.0641(7) Uani 1 1 d . . .
O2 O 0.3847(3) 0.29250(13) 0.6491(2) 0.0678(7) Uani 1 1 d . . .
O3 O 0.1944(3) 0.24943(11) 0.4766(2) 0.0563(6) Uani 1 1 d . . .
S1 S 0.28897(9) 0.30750(4) 0.52649(7) 0.0448(2) Uani 1 1 d . . .
S2 S 0.84381(8) 0.25553(3) 0.55123(7) 0.04079(19) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0526(19) 0.0260(14) 0.0458(16) -0.0055(12) -0.0003(14) -0.0069(13)
C2 0.068(2) 0.0309(15) 0.0409(16) -0.0106(12) 0.0060(15) 0.0028(15)
C3 0.0543(19) 0.0414(16) 0.0360(15) -0.0031(13) 0.0129(14) 0.0111(14)
C4 0.0397(16) 0.0328(14) 0.0340(14) 0.0015(11) 0.0090(12) 0.0011(12)
C5 0.0307(13) 0.0240(12) 0.0224(11) 0.0021(10) 0.0018(10) 0.0004(11)
C6 0.0244(13) 0.0204(12) 0.0250(12) 0.0018(9) 0.0009(10) -0.0036(10)
C7 0.0285(13) 0.0215(12) 0.0283(12) -0.0007(10) 0.0034(10) -0.0033(10)
C8 0.0484(17) 0.0295(14) 0.0399(15) -0.0049(12) 0.0164(13) -0.0097(13)
C9 0.0332(15) 0.0279(13) 0.0358(14) -0.0027(11) 0.0130(12) -0.0036(11)
C10 0.0405(17) 0.0412(16) 0.0366(15) -0.0047(13) 0.0005(12) -0.0039(13)
C11 0.0536(19) 0.0339(15) 0.0401(16) 0.0038(12) -0.0028(14) 0.0073(14)
C12 0.0454(17) 0.0223(13) 0.0394(15) -0.0001(11) 0.0048(12) 0.0024(12)
C13 0.0310(14) 0.0240(13) 0.0351(14) 0.0001(10) 0.0085(11) 0.0017(11)
C14 0.055(2) 0.063(2) 0.055(2) -0.0180(17) 0.0101(17) -0.0198(18)
Cu1 0.0228(2) 0.0163(2) 0.0290(2) 0.00224(16) 0.00392(16) -0.00418(16)
F1 0.0994(17) 0.0635(13) 0.1003(16) -0.0417(12) 0.0308(14) -0.0336(13)
F2 0.0753(16) 0.0887(17) 0.1010(18) -0.0103(13) -0.0091(14) 0.0114(13)
F3 0.0745(15) 0.1093(18) 0.0782(14) -0.0346(13) 0.0439(12) -0.0282(13)
N1 0.0327(12) 0.0224(11) 0.0348(12) -0.0018(9) 0.0040(8) -0.0017(9)
N2 0.0305(12) 0.0209(10) 0.0349(11) -0.0019(9) 0.0082(9) 0.0019(9)
N3 0.0243(11) 0.0168(9) 0.0296(10) -0.0002(8) 0.0044(8) -0.0030(8)
N4 0.0247(11) 0.0228(10) 0.0280(10) 0.0004(8) 0.0053(8) -0.0056(9)
N5 0.0284(11) 0.0202(10) 0.0381(12) -0.0019(9) 0.0076(9) -0.0038(9)
N6 0.0315(12) 0.0358(12) 0.0385(12) -0.0024(10) 0.0129(10) -0.0119(10)
O1 0.0713(16) 0.0695(15) 0.0600(14) -0.0152(12) 0.0345(12) -0.0334(13)
O2 0.0617(16) 0.0783(17) 0.0580(14) -0.0113(12) -0.0036(12) -0.0029(13)
O3 0.0646(15) 0.0501(13) 0.0587(13) -0.0201(10) 0.0228(11) -0.0286(11)
S1 0.0444(4) 0.0502(5) 0.0420(4) -0.0124(3) 0.0138(3) -0.0184(4)
S2 0.0478(4) 0.0247(3) 0.0554(4) -0.0112(3) 0.0243(4) -0.0155(3)

_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
C1 N1 1.330(3) . ?
C1 C2 1.385(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.368(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.359(3) . ?
C5 C6 1.467(3) . ?
C6 N3 1.317(3) . ?
C6 N4 1.360(3) . ?
C7 N5 1.315(3) . ?
C7 N4 1.371(3) . ?
C7 S2 1.736(2) . ?
C8 C9 1.506(3) . ?
C8 S2 1.824(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C13 1.383(3) . ?
C9 C10 1.385(4) . ?
C10 C11 1.373(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(4) . ?
C11 H11 0.9300 . ?
C12 N2 1.338(3) . ?
C12 H12 0.9300 . ?
C13 N2 1.340(3) . ?
C13 H13 0.9300 . ?
C14 F2 1.321(4) . ?
C14 F1 1.330(3) . ?
C14 F3 1.333(4) . ?
C14 S1 1.812(4) . ?
Cu1 N3 1.9754(18) . ?
Cu1 N3 1.9754(18) 3_656 ?
Cu1 N2 2.126(2) 4_565 ?
Cu1 N2 2.126(2) 2_646 ?
Cu1 N1 2.390(2) 3_656 ?
Cu1 N1 2.390(2) . ?
N2 Cu1 2.126(2) 2_656 ?
N3 N5 1.378(3) . ?
N4 N6 1.412(3) . ?
N6 H6B 0.8816 . ?
N6 H6A 0.8745 . ?
O1 S1 1.432(2) . ?
O2 S1 1.444(2) . ?
O3 S1 1.437(2) . ?

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
N1 C1 C2 122.9(3) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.1(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
N1 C5 C4 122.7(2) . . ?
N1 C5 C6 112.2(2) . . ?
C4 C5 C6 125.2(2) . . ?
N3 C6 N4 107.67(19) . . ?
N3 C6 C5 121.6(2) . . ?
N4 C6 C5 130.7(2) . . ?
N5 C7 N4 110.9(2) . . ?
N5 C7 S2 128.14(18) . . ?
N4 C7 S2 120.96(17) . . ?
C9 C8 S2 107.93(17) . . ?
C9 C8 H8A 110.1 . . ?
S2 C8 H8A 110.1 . . ?
C9 C8 H8B 110.1 . . ?
S2 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C13 C9 C10 117.6(2) . . ?
C13 C9 C8 121.9(2) . . ?
C10 C9 C8 120.5(2) . . ?
C11 C10 C9 119.4(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 119.3(3) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
N2 C12 C11 122.5(2) . . ?
N2 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
N2 C13 C9 123.5(2) . . ?
N2 C13 H13 118.2 . . ?
C9 C13 H13 118.2 . . ?
F2 C14 F1 108.4(3) . . ?
F2 C14 F3 107.2(3) . . ?
F1 C14 F3 106.5(3) . . ?
F2 C14 S1 112.4(2) . . ?
F1 C14 S1 110.8(2) . . ?
F3 C14 S1 111.2(3) . . ?
N3 Cu1 N3 180.00(7) . 3_656 ?
N3 Cu1 N2 90.45(8) . 4_565 ?
N3 Cu1 N2 89.55(8) 3_656 4_565 ?
N3 Cu1 N2 89.55(8) . 2_646 ?
N3 Cu1 N2 90.45(8) 3_656 2_646 ?
N2 Cu1 N2 180.00(9) 4_565 2_646 ?
N3 Cu1 N1 105.09(7) . 3_656 ?
N3 Cu1 N1 74.91(7) 3_656 3_656 ?
N2 Cu1 N1 87.29(7) 4_565 3_656 ?
N2 Cu1 N1 92.71(7) 2_646 3_656 ?
N3 Cu1 N1 74.91(7) . . ?
N3 Cu1 N1 105.09(7) 3_656 . ?
N2 Cu1 N1 92.71(7) 4_565 . ?
N2 Cu1 N1 87.29(7) 2_646 . ?
N1 Cu1 N1 180.0 3_656 . ?
C1 N1 C5 117.6(2) . . ?
C1 N1 Cu1 131.84(19) . . ?
C5 N1 Cu1 110.19(15) . . ?
C12 N2 C13 117.7(2) . . ?
C12 N2 Cu1 119.20(16) . 2_656 ?
C13 N2 Cu1 123.11(17) . 2_656 ?
C6 N3 N5 110.46(18) . . ?
C6 N3 Cu1 120.81(15) . . ?
N5 N3 Cu1 128.73(15) . . ?
C6 N4 C7 105.94(19) . . ?
C6 N4 N6 125.71(19) . . ?
C7 N4 N6 128.35(19) . . ?
C7 N5 N3 105.03(19) . . ?
N4 N6 H6B 109.0 . . ?
N4 N6 H6A 109.1 . . ?
H6B N6 H6A 106.7 . . ?
O1 S1 O3 115.17(13) . . ?
O1 S1 O2 115.25(15) . . ?
O3 S1 O2 113.90(15) . . ?
O1 S1 C14 103.37(16) . . ?
O3 S1 C14 104.76(14) . . ?
O2 S1 C14 102.17(15) . . ?
C7 S2 C8 99.82(12) . . ?

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
N1 C1 C2 C3 0.0(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 N1 0.3(4) . . . . ?
C3 C4 C5 C6 180.0(2) . . . . ?
N1 C5 C6 N3 4.6(3) . . . . ?
C4 C5 C6 N3 -175.2(2) . . . . ?
N1 C5 C6 N4 -174.7(2) . . . . ?
C4 C5 C6 N4 5.6(4) . . . . ?
S2 C8 C9 C13 -107.0(2) . . . . ?
S2 C8 C9 C10 73.5(3) . . . . ?
C13 C9 C10 C11 2.1(4) . . . . ?
C8 C9 C10 C11 -178.4(3) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C10 C11 C12 N2 -2.0(4) . . . . ?
C10 C9 C13 N2 -2.6(4) . . . . ?
C8 C9 C13 N2 177.9(2) . . . . ?
C2 C1 N1 C5 0.0(4) . . . . ?
C2 C1 N1 Cu1 -172.6(2) . . . . ?
C4 C5 N1 C1 -0.1(3) . . . . ?
C6 C5 N1 C1 -179.9(2) . . . . ?
C4 C5 N1 Cu1 174.00(18) . . . . ?
C6 C5 N1 Cu1 -5.8(2) . . . . ?
N3 Cu1 N1 C1 177.6(2) . . . . ?
N3 Cu1 N1 C1 -2.4(2) 3_656 . . . ?
N2 Cu1 N1 C1 -92.7(2) 4_565 . . . ?
N2 Cu1 N1 C1 87.3(2) 2_646 . . . ?
N1 Cu1 N1 C1 52(100) 3_656 . . . ?
N3 Cu1 N1 C5 4.62(15) . . . . ?
N3 Cu1 N1 C5 -175.38(15) 3_656 . . . ?
N2 Cu1 N1 C5 94.36(16) 4_565 . . . ?
N2 Cu1 N1 C5 -85.64(16) 2_646 . . . ?
N1 Cu1 N1 C5 -121(100) 3_656 . . . ?
C11 C12 N2 C13 1.6(4) . . . . ?
C11 C12 N2 Cu1 -176.3(2) . . . 2_656 ?
C9 C13 N2 C12 0.7(4) . . . . ?
C9 C13 N2 Cu1 178.62(18) . . . 2_656 ?
N4 C6 N3 N5 -0.7(2) . . . . ?
C5 C6 N3 N5 179.8(2) . . . . ?
N4 C6 N3 Cu1 179.25(14) . . . . ?
C5 C6 N3 Cu1 -0.2(3) . . . . ?
N3 Cu1 N3 C6 30(6) 3_656 . . . ?
N2 Cu1 N3 C6 -95.02(18) 4_565 . . . ?
N2 Cu1 N3 C6 84.98(18) 2_646 . . . ?
N1 Cu1 N3 C6 177.67(17) 3_656 . . . ?
N1 Cu1 N3 C6 -2.33(17) . . . . ?
N3 Cu1 N3 N5 -150(6) 3_656 . . . ?
N2 Cu1 N3 N5 84.96(19) 4_565 . . . ?
N2 Cu1 N3 N5 -95.04(19) 2_646 . . . ?
N1 Cu1 N3 N5 -2.4(2) 3_656 . . . ?
N1 Cu1 N3 N5 177.6(2) . . . . ?
N3 C6 N4 C7 0.5(2) . . . . ?
C5 C6 N4 C7 179.8(2) . . . . ?
N3 C6 N4 N6 179.7(2) . . . . ?
C5 C6 N4 N6 -0.9(4) . . . . ?
N5 C7 N4 C6 -0.1(3) . . . . ?
S2 C7 N4 C6 179.51(17) . . . . ?
N5 C7 N4 N6 -179.3(2) . . . . ?
S2 C7 N4 N6 0.3(3) . . . . ?
N4 C7 N5 N3 -0.4(3) . . . . ?
S2 C7 N5 N3 -179.90(18) . . . . ?
C6 N3 N5 C7 0.7(2) . . . . ?
Cu1 N3 N5 C7 -179.30(16) . . . . ?
F2 C14 S1 O1 67.6(3) . . . . ?
F1 C14 S1 O1 -53.8(3) . . . . ?
F3 C14 S1 O1 -172.1(2) . . . . ?
F2 C14 S1 O3 -53.3(3) . . . . ?
F1 C14 S1 O3 -174.8(2) . . . . ?
F3 C14 S1 O3 66.9(3) . . . . ?
F2 C14 S1 O2 -172.4(2) . . . . ?
F1 C14 S1 O2 66.2(3) . . . . ?
F3 C14 S1 O2 -52.1(3) . . . . ?
N5 C7 S2 C8 17.6(3) . . . . ?
N4 C7 S2 C8 -161.9(2) . . . . ?
C9 C8 S2 C7 -165.52(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6A O3 0.87 2.22 2.969(3) 144.0 1_655
N6 H6B O2 0.88 2.09 2.967(3) 171.1 4_665

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 959228'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_exp_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24 Cu F6 N12 O6 S4'
_chemical_formula_weight         930.37

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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 '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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   9.2224(7)
_cell_length_b                   18.8786(13)
_cell_length_c                   10.4661(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.366(7)
_cell_angle_gamma                90.00
_cell_volume                     1792.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    323(2)
_cell_measurement_reflns_used    1752
_cell_measurement_theta_min      2.4859
_cell_measurement_theta_max      28.3929

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             942
_exptl_absorpt_coefficient_mu    0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7603
_exptl_absorpt_correction_T_max  0.9289
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      323(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  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         13043
_diffrn_standards_interval_count 0.3
_diffrn_standards_interval_time  2
_diffrn_standards_decay_%        none
_diffrn_reflns_number            11387
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_sigmaI/netI    0.0660
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3348
_reflns_number_gt                2358
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0268P)^2^+0.4826P] where P=(Fo^2^+2Fc^2^)/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         3348
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.0996
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
C1 C 0.6776(5) -0.11361(19) 0.3254(4) 0.0473(10) Uani 1 1 d . . .
H1 H 0.5998 -0.1450 0.3250 0.057 Uiso 1 1 calc R . .
C2 C 0.7959(5) -0.1351(2) 0.2702(4) 0.0545(12) Uani 1 1 d . . .
H2 H 0.7969 -0.1801 0.2342 0.065 Uiso 1 1 calc R . .
C3 C 0.9112(5) -0.0899(2) 0.2688(4) 0.0474(10) Uani 1 1 d . . .
H3 H 0.9913 -0.1035 0.2318 0.057 Uiso 1 1 calc R . .
C4 C 0.9066(4) -0.02280(19) 0.3241(3) 0.0384(9) Uani 1 1 d . . .
H4 H 0.9836 0.0091 0.3250 0.046 Uiso 1 1 calc R . .
C5 C 0.7854(4) -0.00488(17) 0.3773(3) 0.0281(8) Uani 1 1 d . . .
C6 C 0.7632(3) 0.06279(16) 0.4390(3) 0.0263(8) Uani 1 1 d . . .
C7 C 0.7747(4) 0.17122(17) 0.5164(3) 0.0299(8) Uani 1 1 d . . .
C8 C 0.7430(4) 0.27959(19) 0.6804(4) 0.0437(10) Uani 1 1 d . . .
H8A H 0.6399 0.2669 0.6556 0.052 Uiso 1 1 calc R . .
H8B H 0.7834 0.2546 0.7599 0.052 Uiso 1 1 calc R . .
C9 C 0.7582(4) 0.35854(18) 0.7016(4) 0.0345(9) Uani 1 1 d . . .
C10 C 0.6815(4) 0.4049(2) 0.6122(4) 0.0446(10) Uani 1 1 d . . .
H10 H 0.6181 0.3879 0.5394 0.054 Uiso 1 1 calc R . .
C11 C 0.7003(4) 0.4766(2) 0.6323(4) 0.0506(11) Uani 1 1 d . . .
H11 H 0.6495 0.5087 0.5732 0.061 Uiso 1 1 calc R . .
C12 C 0.7942(4) 0.50023(19) 0.7398(4) 0.0406(9) Uani 1 1 d . . .
H12 H 0.8086 0.5488 0.7504 0.049 Uiso 1 1 calc R . .
C13 C 0.8469(4) 0.38664(18) 0.8101(3) 0.0327(9) Uani 1 1 d . . .
H13 H 0.8958 0.3556 0.8723 0.039 Uiso 1 1 calc R . .
C14 C 0.1661(5) 0.3741(3) 0.5720(5) 0.0669(14) Uani 1 1 d . . .
Cu1 Cu 0.5000 0.0000 0.5000 0.02654(17) Uani 1 2 d S . .
F1 F 0.2377(3) 0.43326(14) 0.6104(3) 0.0960(10) Uani 1 1 d . . .
F2 F 0.0561(3) 0.38927(17) 0.4766(4) 0.1042(11) Uani 1 1 d . . .
F3 F 0.1056(3) 0.35223(16) 0.6722(3) 0.0922(10) Uani 1 1 d . . .
N1 N 0.6703(3) -0.04996(15) 0.3792(3) 0.0356(7) Uani 1 1 d . . .
N2 N 0.8663(3) 0.45683(14) 0.8305(3) 0.0313(7) Uani 1 1 d . . .
N3 N 0.6494(3) 0.07464(13) 0.4955(3) 0.0268(6) Uani 1 1 d . . .
N4 N 0.8453(3) 0.12348(14) 0.4499(3) 0.0290(7) Uani 1 1 d . . .
N5 N 0.6542(3) 0.14190(14) 0.5457(3) 0.0323(7) Uani 1 1 d . . .
N6 N 0.9778(3) 0.13342(15) 0.4021(3) 0.0388(8) Uani 1 1 d . . .
H6B H 0.9591 0.1581 0.3292 0.047 Uiso 1 1 d R . .
H6A H 1.0386 0.1588 0.4580 0.047 Uiso 1 1 d R . .
O1 O 0.3571(3) 0.34314(16) 0.4326(3) 0.0739(10) Uani 1 1 d . . .
O2 O 0.3838(3) 0.29303(17) 0.6496(3) 0.0760(10) Uani 1 1 d . . .
O3 O 0.1938(3) 0.24976(15) 0.4776(3) 0.0639(9) Uani 1 1 d . . .
S1 S 0.28871(12) 0.30752(6) 0.52705(11) 0.0511(3) Uani 1 1 d . . .
S2 S 0.84329(11) 0.25535(5) 0.55193(11) 0.0472(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.060(3) 0.026(2) 0.051(3) -0.0069(19) -0.002(2) -0.0097(18)
C2 0.079(3) 0.033(3) 0.049(3) -0.014(2) 0.005(2) 0.006(2)
C3 0.058(3) 0.043(3) 0.043(3) -0.003(2) 0.014(2) 0.011(2)
C4 0.043(2) 0.037(2) 0.035(2) -0.0018(18) 0.0070(18) 0.0023(17)
C5 0.036(2) 0.0210(19) 0.0258(19) 0.0033(15) 0.0014(15) 0.0013(15)
C6 0.0256(18) 0.0221(19) 0.030(2) 0.0057(15) 0.0013(15) -0.0016(14)
C7 0.0307(19) 0.024(2) 0.034(2) 0.0003(16) 0.0041(16) -0.0020(15)
C8 0.056(3) 0.034(2) 0.045(2) -0.0052(19) 0.017(2) -0.0096(18)
C9 0.038(2) 0.026(2) 0.041(2) -0.0040(17) 0.0127(18) -0.0035(15)
C10 0.045(2) 0.042(3) 0.045(3) -0.006(2) 0.0002(19) -0.0038(18)
C11 0.060(3) 0.036(2) 0.051(3) 0.002(2) -0.002(2) 0.0073(19)
C12 0.049(2) 0.025(2) 0.046(2) -0.0002(19) 0.0058(19) 0.0022(17)
C13 0.035(2) 0.025(2) 0.040(2) 0.0016(16) 0.0111(18) 0.0014(15)
C14 0.066(3) 0.065(3) 0.072(4) -0.023(3) 0.016(3) -0.028(3)
Cu1 0.0267(3) 0.0182(3) 0.0345(4) 0.0023(3) 0.0051(3) -0.0042(2)
F1 0.112(2) 0.069(2) 0.113(3) -0.0443(18) 0.037(2) -0.0346(17)
F2 0.085(2) 0.101(3) 0.116(3) -0.012(2) -0.011(2) 0.0103(18)
F3 0.082(2) 0.121(3) 0.086(2) -0.0383(19) 0.0468(19) -0.0292(17)
N1 0.0358(17) 0.0284(18) 0.0402(19) 0.0001(14) 0.0007(14) -0.0063(13)
N2 0.0330(16) 0.0229(17) 0.0378(18) -0.0038(14) 0.0061(14) 0.0029(12)
N3 0.0274(15) 0.0171(15) 0.0350(17) 0.0011(13) 0.0033(13) -0.0030(11)
N4 0.0309(16) 0.0241(16) 0.0323(17) 0.0020(13) 0.0066(13) -0.0054(12)
N5 0.0330(16) 0.0224(16) 0.0422(19) -0.0035(14) 0.0085(14) -0.0046(12)
N6 0.0352(18) 0.0391(19) 0.045(2) -0.0026(15) 0.0136(15) -0.0128(14)
O1 0.084(2) 0.079(2) 0.069(2) -0.0182(18) 0.0397(19) -0.0395(18)
O2 0.066(2) 0.092(3) 0.062(2) -0.0080(19) -0.0082(18) -0.0027(18)
O3 0.074(2) 0.056(2) 0.067(2) -0.0240(16) 0.0267(17) -0.0308(15)
S1 0.0498(7) 0.0561(7) 0.0504(7) -0.0142(6) 0.0168(6) -0.0193(5)
S2 0.0553(7) 0.0287(6) 0.0641(7) -0.0127(5) 0.0280(6) -0.0176(4)

_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
C1 N1 1.334(4) . ?
C1 C2 1.384(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.366(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.396(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(4) . ?
C4 H4 0.9300 . ?
C5 N1 1.364(4) . ?
C5 C6 1.462(4) . ?
C6 N3 1.313(4) . ?
C6 N4 1.367(4) . ?
C7 N5 1.326(4) . ?
C7 N4 1.373(4) . ?
C7 S2 1.725(3) . ?
C8 C9 1.510(5) . ?
C8 S2 1.822(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.379(5) . ?
C9 C13 1.381(5) . ?
C10 C11 1.377(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.364(5) . ?
C11 H11 0.9300 . ?
C12 N2 1.337(4) . ?
C12 H12 0.9300 . ?
C13 N2 1.349(4) . ?
C13 H13 0.9300 . ?
C14 F2 1.321(6) . ?
C14 F1 1.323(5) . ?
C14 F3 1.338(5) . ?
C14 S1 1.808(5) . ?
Cu1 N3 1.977(2) . ?
Cu1 N3 1.977(2) 3_656 ?
Cu1 N2 2.132(3) 4_565 ?
Cu1 N2 2.132(3) 2_646 ?
Cu1 N1 2.380(3) . ?
Cu1 N1 2.380(3) 3_656 ?
N2 Cu1 2.132(3) 2_656 ?
N3 N5 1.372(3) . ?
N4 N6 1.414(3) . ?
N6 H6B 0.8843 . ?
N6 H6A 0.8765 . ?
O1 S1 1.432(3) . ?
O2 S1 1.444(3) . ?
O3 S1 1.435(3) . ?

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
N1 C1 C2 122.9(4) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 119.7(4) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 118.7(4) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 122.9(3) . . ?
N1 C5 C6 111.6(3) . . ?
C4 C5 C6 125.5(3) . . ?
N3 C6 N4 107.2(3) . . ?
N3 C6 C5 122.3(3) . . ?
N4 C6 C5 130.5(3) . . ?
N5 C7 N4 109.7(3) . . ?
N5 C7 S2 128.7(3) . . ?
N4 C7 S2 121.6(2) . . ?
C9 C8 S2 108.1(2) . . ?
C9 C8 H8A 110.1 . . ?
S2 C8 H8A 110.1 . . ?
C9 C8 H8B 110.1 . . ?
S2 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C10 C9 C13 118.0(3) . . ?
C10 C9 C8 120.3(3) . . ?
C13 C9 C8 121.7(3) . . ?
C11 C10 C9 119.0(4) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C12 C11 C10 119.4(4) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
N2 C12 C11 123.1(4) . . ?
N2 C12 H12 118.5 . . ?
C11 C12 H12 118.5 . . ?
N2 C13 C9 123.3(3) . . ?
N2 C13 H13 118.3 . . ?
C9 C13 H13 118.3 . . ?
F2 C14 F1 108.6(5) . . ?
F2 C14 F3 106.7(4) . . ?
F1 C14 F3 106.2(4) . . ?
F2 C14 S1 112.7(3) . . ?
F1 C14 S1 111.4(3) . . ?
F3 C14 S1 111.0(4) . . ?
N3 Cu1 N3 180.00(14) . 3_656 ?
N3 Cu1 N2 90.51(10) . 4_565 ?
N3 Cu1 N2 89.49(10) 3_656 4_565 ?
N3 Cu1 N2 89.49(10) . 2_646 ?
N3 Cu1 N2 90.51(10) 3_656 2_646 ?
N2 Cu1 N2 180.00(11) 4_565 2_646 ?
N3 Cu1 N1 74.98(10) . . ?
N3 Cu1 N1 105.02(10) 3_656 . ?
N2 Cu1 N1 92.72(10) 4_565 . ?
N2 Cu1 N1 87.28(10) 2_646 . ?
N3 Cu1 N1 105.02(10) . 3_656 ?
N3 Cu1 N1 74.98(10) 3_656 3_656 ?
N2 Cu1 N1 87.28(10) 4_565 3_656 ?
N2 Cu1 N1 92.72(10) 2_646 3_656 ?
N1 Cu1 N1 180.0 . 3_656 ?
C1 N1 C5 117.2(3) . . ?
C1 N1 Cu1 132.0(2) . . ?
C5 N1 Cu1 110.5(2) . . ?
C12 N2 C13 117.1(3) . . ?
C12 N2 Cu1 119.7(2) . 2_656 ?
C13 N2 Cu1 123.2(2) . 2_656 ?
C6 N3 N5 110.9(2) . . ?
C6 N3 Cu1 120.4(2) . . ?
N5 N3 Cu1 128.7(2) . . ?
C6 N4 C7 106.7(3) . . ?
C6 N4 N6 125.6(3) . . ?
C7 N4 N6 127.7(3) . . ?
C7 N5 N3 105.6(3) . . ?
N4 N6 H6B 109.2 . . ?
N4 N6 H6A 109.0 . . ?
H6B N6 H6A 106.8 . . ?
O1 S1 O3 115.04(18) . . ?
O1 S1 O2 115.4(2) . . ?
O3 S1 O2 114.2(2) . . ?
O1 S1 C14 103.1(2) . . ?
O3 S1 C14 104.61(19) . . ?
O2 S1 C14 102.0(2) . . ?
C7 S2 C8 100.09(16) . . ?

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
N1 C1 C2 C3 -0.4(6) . . . . ?
C1 C2 C3 C4 0.2(6) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C3 C4 C5 N1 0.5(5) . . . . ?
C3 C4 C5 C6 179.8(3) . . . . ?
N1 C5 C6 N3 4.0(4) . . . . ?
C4 C5 C6 N3 -175.4(3) . . . . ?
N1 C5 C6 N4 -175.0(3) . . . . ?
C4 C5 C6 N4 5.6(6) . . . . ?
S2 C8 C9 C10 73.6(4) . . . . ?
S2 C8 C9 C13 -107.0(3) . . . . ?
C13 C9 C10 C11 2.2(5) . . . . ?
C8 C9 C10 C11 -178.4(3) . . . . ?
C9 C10 C11 C12 0.1(6) . . . . ?
C10 C11 C12 N2 -2.4(6) . . . . ?
C10 C9 C13 N2 -2.5(5) . . . . ?
C8 C9 C13 N2 178.1(3) . . . . ?
C2 C1 N1 C5 0.6(6) . . . . ?
C2 C1 N1 Cu1 -172.8(3) . . . . ?
C4 C5 N1 C1 -0.7(5) . . . . ?
C6 C5 N1 C1 179.9(3) . . . . ?
C4 C5 N1 Cu1 174.1(3) . . . . ?
C6 C5 N1 Cu1 -5.3(3) . . . . ?
N3 Cu1 N1 C1 178.1(4) . . . . ?
N3 Cu1 N1 C1 -1.9(4) 3_656 . . . ?
N2 Cu1 N1 C1 -92.1(3) 4_565 . . . ?
N2 Cu1 N1 C1 87.9(3) 2_646 . . . ?
N1 Cu1 N1 C1 65(100) 3_656 . . . ?
N3 Cu1 N1 C5 4.3(2) . . . . ?
N3 Cu1 N1 C5 -175.7(2) 3_656 . . . ?
N2 Cu1 N1 C5 94.1(2) 4_565 . . . ?
N2 Cu1 N1 C5 -85.9(2) 2_646 . . . ?
N1 Cu1 N1 C5 -109(100) 3_656 . . . ?
C11 C12 N2 C13 2.2(5) . . . . ?
C11 C12 N2 Cu1 -176.3(3) . . . 2_656 ?
C9 C13 N2 C12 0.3(5) . . . . ?
C9 C13 N2 Cu1 178.7(2) . . . 2_656 ?
N4 C6 N3 N5 -0.8(3) . . . . ?
C5 C6 N3 N5 -180.0(3) . . . . ?
N4 C6 N3 Cu1 179.3(2) . . . . ?
C5 C6 N3 Cu1 0.1(4) . . . . ?
N3 Cu1 N3 C6 120(100) 3_656 . . . ?
N2 Cu1 N3 C6 -95.0(2) 4_565 . . . ?
N2 Cu1 N3 C6 85.0(2) 2_646 . . . ?
N1 Cu1 N3 C6 -2.3(2) . . . . ?
N1 Cu1 N3 C6 177.7(2) 3_656 . . . ?
N3 Cu1 N3 N5 -60(100) 3_656 . . . ?
N2 Cu1 N3 N5 85.1(3) 4_565 . . . ?
N2 Cu1 N3 N5 -94.9(3) 2_646 . . . ?
N1 Cu1 N3 N5 177.8(3) . . . . ?
N1 Cu1 N3 N5 -2.2(3) 3_656 . . . ?
N3 C6 N4 C7 0.5(3) . . . . ?
C5 C6 N4 C7 179.6(3) . . . . ?
N3 C6 N4 N6 179.9(3) . . . . ?
C5 C6 N4 N6 -0.9(5) . . . . ?
N5 C7 N4 C6 0.0(4) . . . . ?
S2 C7 N4 C6 179.6(2) . . . . ?
N5 C7 N4 N6 -179.4(3) . . . . ?
S2 C7 N4 N6 0.2(5) . . . . ?
N4 C7 N5 N3 -0.4(4) . . . . ?
S2 C7 N5 N3 179.9(3) . . . . ?
C6 N3 N5 C7 0.7(4) . . . . ?
Cu1 N3 N5 C7 -179.4(2) . . . . ?
F2 C14 S1 O1 67.9(4) . . . . ?
F1 C14 S1 O1 -54.4(4) . . . . ?
F3 C14 S1 O1 -172.5(3) . . . . ?
F2 C14 S1 O3 -52.7(4) . . . . ?
F1 C14 S1 O3 -175.1(4) . . . . ?
F3 C14 S1 O3 66.9(4) . . . . ?
F2 C14 S1 O2 -172.0(3) . . . . ?
F1 C14 S1 O2 65.6(4) . . . . ?
F3 C14 S1 O2 -52.4(4) . . . . ?
N5 C7 S2 C8 17.6(4) . . . . ?
N4 C7 S2 C8 -162.0(3) . . . . ?
C9 C8 S2 C7 -165.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6A O3 0.88 2.22 2.975(4) 144.0 1_655
N6 H6B O2 0.88 2.10 2.973(4) 170.8 4_665

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 959229'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_exp_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24 Cu F6 N12 O6 S4'
_chemical_formula_weight         930.37

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'
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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   9.2249(9)
_cell_length_b                   18.8564(13)
_cell_length_c                   10.4413(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.292(10)
_cell_angle_gamma                90.00
_cell_volume                     1787.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    353(2)
_cell_measurement_reflns_used    1367
_cell_measurement_theta_min      2.4860
_cell_measurement_theta_max      28.4338

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             942
_exptl_absorpt_coefficient_mu    0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7597
_exptl_absorpt_correction_T_max  0.9287
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      353(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  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         7623
_diffrn_standards_interval_count 0.3
_diffrn_standards_interval_time  5
_diffrn_standards_decay_%        none
_diffrn_reflns_number            6596
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0574
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3332
_reflns_number_gt                2444
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0293P)^2^+0.6393P] where P=(Fo^2^+2Fc^2^)/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         3332
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1007
_refine_ls_wR_factor_gt          0.0874
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
C1 C 0.6766(5) -0.1127(2) 0.3261(4) 0.0526(10) Uani 1 1 d . . .
H1 H 0.5984 -0.1439 0.3259 0.063 Uiso 1 1 calc R . .
C2 C 0.7950(5) -0.1347(2) 0.2702(4) 0.0602(12) Uani 1 1 d . . .
H2 H 0.7961 -0.1797 0.2343 0.072 Uiso 1 1 calc R . .
C3 C 0.9099(5) -0.0889(2) 0.2688(4) 0.0537(11) Uani 1 1 d . . .
H3 H 0.9896 -0.1023 0.2309 0.064 Uiso 1 1 calc R . .
C4 C 0.9060(4) -0.0227(2) 0.3243(3) 0.0423(9) Uani 1 1 d . . .
H4 H 0.9835 0.0091 0.3259 0.051 Uiso 1 1 calc R . .
C5 C 0.7843(4) -0.00456(17) 0.3774(3) 0.0314(7) Uani 1 1 d . . .
C6 C 0.7630(3) 0.06337(16) 0.4398(3) 0.0284(7) Uani 1 1 d . . .
C7 C 0.7734(4) 0.17092(17) 0.5166(3) 0.0334(8) Uani 1 1 d . . .
C8 C 0.7424(4) 0.27921(19) 0.6808(4) 0.0469(10) Uani 1 1 d . . .
H8A H 0.6393 0.2665 0.6558 0.056 Uiso 1 1 calc R . .
H8B H 0.7825 0.2542 0.7604 0.056 Uiso 1 1 calc R . .
C9 C 0.7575(4) 0.35830(18) 0.7018(3) 0.0372(8) Uani 1 1 d . . .
C10 C 0.6814(4) 0.4049(2) 0.6123(4) 0.0483(10) Uani 1 1 d . . .
H10 H 0.6181 0.3880 0.5392 0.058 Uiso 1 1 calc R . .
C11 C 0.7001(5) 0.4762(2) 0.6322(4) 0.0540(11) Uani 1 1 d . . .
H11 H 0.6496 0.5083 0.5729 0.065 Uiso 1 1 calc R . .
C12 C 0.7941(4) 0.49985(19) 0.7404(4) 0.0435(9) Uani 1 1 d . . .
H12 H 0.8083 0.5484 0.7516 0.052 Uiso 1 1 calc R . .
C13 C 0.8463(4) 0.38656(18) 0.8101(3) 0.0370(8) Uani 1 1 d . . .
H13 H 0.8953 0.3556 0.8725 0.044 Uiso 1 1 calc R . .
C14 C 0.1660(5) 0.3734(3) 0.5721(5) 0.0702(14) Uani 1 1 d . . .
Cu1 Cu 0.5000 0.0000 0.5000 0.02879(17) Uani 1 2 d S . .
F1 F 0.2377(4) 0.43300(15) 0.6099(3) 0.1065(11) Uani 1 1 d . . .
F2 F 0.0560(4) 0.38908(18) 0.4768(4) 0.1127(11) Uani 1 1 d . . .
F3 F 0.1054(3) 0.35251(17) 0.6720(3) 0.1022(11) Uani 1 1 d . . .
N1 N 0.6700(3) -0.04973(15) 0.3795(3) 0.0385(7) Uani 1 1 d . . .
N2 N 0.8655(3) 0.45651(14) 0.8299(3) 0.0351(7) Uani 1 1 d . . .
N3 N 0.6485(3) 0.07467(13) 0.4961(2) 0.0294(6) Uani 1 1 d . . .
N4 N 0.8448(3) 0.12347(14) 0.4502(2) 0.0311(6) Uani 1 1 d . . .
N5 N 0.6536(3) 0.14235(14) 0.5465(3) 0.0354(7) Uani 1 1 d . . .
N6 N 0.9772(3) 0.13356(15) 0.4017(3) 0.0418(7) Uani 1 1 d . . .
H6B H 0.9584 0.1583 0.3288 0.050 Uiso 1 1 d R . .
H6A H 1.0380 0.1589 0.4576 0.050 Uiso 1 1 d R . .
O1 O 0.3568(4) 0.34327(17) 0.4327(3) 0.0802(10) Uani 1 1 d . . .
O2 O 0.3829(4) 0.29258(19) 0.6494(3) 0.0843(10) Uani 1 1 d . . .
O3 O 0.1942(3) 0.24951(15) 0.4781(3) 0.0704(9) Uani 1 1 d . . .
S1 S 0.28833(12) 0.30739(6) 0.52725(10) 0.0559(3) Uani 1 1 d . . .
S2 S 0.84258(12) 0.25513(5) 0.55270(10) 0.0508(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.064(3) 0.032(2) 0.060(3) -0.005(2) 0.004(2) -0.007(2)
C2 0.085(3) 0.038(2) 0.056(3) -0.013(2) 0.007(2) 0.002(2)
C3 0.068(3) 0.050(3) 0.046(2) -0.002(2) 0.018(2) 0.012(2)
C4 0.045(2) 0.041(2) 0.042(2) 0.0008(18) 0.0098(17) 0.0027(18)
C5 0.0392(19) 0.0246(17) 0.0285(17) 0.0044(15) 0.0015(14) 0.0011(16)
C6 0.0318(18) 0.0233(17) 0.0285(17) 0.0055(14) 0.0016(14) -0.0053(15)
C7 0.0377(19) 0.0220(18) 0.040(2) -0.0013(15) 0.0050(15) -0.0073(16)
C8 0.058(2) 0.034(2) 0.053(2) -0.0065(19) 0.0194(19) -0.0133(19)
C9 0.039(2) 0.032(2) 0.044(2) -0.0044(17) 0.0153(17) -0.0074(17)
C10 0.054(2) 0.045(2) 0.043(2) -0.006(2) 0.0034(18) -0.006(2)
C11 0.065(3) 0.041(2) 0.051(2) 0.005(2) 0.000(2) 0.010(2)
C12 0.053(2) 0.0258(19) 0.050(2) 0.0032(18) 0.0043(19) 0.0038(18)
C13 0.038(2) 0.028(2) 0.046(2) -0.0013(17) 0.0117(17) 0.0024(16)
C14 0.068(3) 0.075(4) 0.068(3) -0.021(3) 0.012(3) -0.028(3)
Cu1 0.0290(3) 0.0197(3) 0.0377(3) 0.0027(3) 0.0062(2) -0.0044(2)
F1 0.124(3) 0.078(2) 0.125(3) -0.051(2) 0.043(2) -0.042(2)
F2 0.096(2) 0.105(3) 0.127(3) -0.010(2) -0.010(2) 0.013(2)
F3 0.092(2) 0.131(3) 0.098(2) -0.043(2) 0.0551(18) -0.033(2)
N1 0.0431(18) 0.0267(16) 0.0435(17) -0.0017(14) 0.0019(14) -0.0060(14)
N2 0.0386(16) 0.0253(16) 0.0430(17) -0.0012(14) 0.0115(13) 0.0034(14)
N3 0.0298(15) 0.0220(14) 0.0361(15) 0.0011(12) 0.0053(12) -0.0027(12)
N4 0.0326(15) 0.0268(15) 0.0349(16) 0.0018(13) 0.0089(12) -0.0061(13)
N5 0.0354(16) 0.0261(15) 0.0457(17) -0.0013(13) 0.0102(13) -0.0048(13)
N6 0.0377(17) 0.0410(18) 0.0494(18) -0.0003(15) 0.0150(14) -0.0105(15)
O1 0.089(2) 0.090(2) 0.073(2) -0.0191(18) 0.0430(18) -0.041(2)
O2 0.077(2) 0.098(3) 0.072(2) -0.010(2) -0.0043(18) -0.003(2)
O3 0.081(2) 0.062(2) 0.074(2) -0.0272(16) 0.0283(17) -0.0368(17)
S1 0.0542(6) 0.0624(7) 0.0541(7) -0.0157(6) 0.0173(5) -0.0204(6)
S2 0.0595(7) 0.0302(5) 0.0699(7) -0.0135(5) 0.0308(5) -0.0192(5)

_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
C1 N1 1.318(4) . ?
C1 C2 1.390(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9300 . ?
C5 N1 1.358(4) . ?
C5 C6 1.466(4) . ?
C6 N3 1.315(4) . ?
C6 N4 1.355(4) . ?
C7 N5 1.316(4) . ?
C7 N4 1.370(4) . ?
C7 S2 1.728(3) . ?
C8 C9 1.510(5) . ?
C8 S2 1.814(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C13 1.379(5) . ?
C9 C10 1.380(5) . ?
C10 C11 1.366(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(5) . ?
C11 H11 0.9300 . ?
C12 N2 1.325(4) . ?
C12 H12 0.9300 . ?
C13 N2 1.342(4) . ?
C13 H13 0.9300 . ?
C14 F2 1.321(6) . ?
C14 F1 1.328(5) . ?
C14 F3 1.328(5) . ?
C14 S1 1.798(5) . ?
Cu1 N3 1.970(2) . ?
Cu1 N3 1.970(2) 3_656 ?
Cu1 N2 2.140(3) 2_646 ?
Cu1 N2 2.140(3) 4_565 ?
Cu1 N1 2.372(3) 3_656 ?
Cu1 N1 2.372(3) . ?
N2 Cu1 2.140(3) 2_656 ?
N3 N5 1.378(3) . ?
N4 N6 1.416(3) . ?
N6 H6B 0.8827 . ?
N6 H6A 0.8759 . ?
O1 S1 1.434(3) . ?
O2 S1 1.438(3) . ?
O3 S1 1.431(3) . ?

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
N1 C1 C2 123.0(4) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 119.0(4) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.2(4) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 118.4(4) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 122.7(3) . . ?
N1 C5 C6 112.0(3) . . ?
C4 C5 C6 125.3(3) . . ?
N3 C6 N4 108.0(3) . . ?
N3 C6 C5 121.5(3) . . ?
N4 C6 C5 130.5(3) . . ?
N5 C7 N4 110.6(3) . . ?
N5 C7 S2 128.1(3) . . ?
N4 C7 S2 121.2(2) . . ?
C9 C8 S2 107.9(2) . . ?
C9 C8 H8A 110.1 . . ?
S2 C8 H8A 110.1 . . ?
C9 C8 H8B 110.1 . . ?
S2 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C13 C9 C10 117.7(3) . . ?
C13 C9 C8 121.8(3) . . ?
C10 C9 C8 120.5(3) . . ?
C11 C10 C9 119.2(4) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 119.3(4) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
N2 C12 C11 122.8(3) . . ?
N2 C12 H12 118.6 . . ?
C11 C12 H12 118.6 . . ?
N2 C13 C9 123.3(3) . . ?
N2 C13 H13 118.4 . . ?
C9 C13 H13 118.4 . . ?
F2 C14 F1 108.1(5) . . ?
F2 C14 F3 106.5(4) . . ?
F1 C14 F3 106.0(4) . . ?
F2 C14 S1 113.1(3) . . ?
F1 C14 S1 111.1(3) . . ?
F3 C14 S1 111.8(4) . . ?
N3 Cu1 N3 180.00(10) . 3_656 ?
N3 Cu1 N2 89.36(10) . 2_646 ?
N3 Cu1 N2 90.64(10) 3_656 2_646 ?
N3 Cu1 N2 90.64(10) . 4_565 ?
N3 Cu1 N2 89.36(10) 3_656 4_565 ?
N2 Cu1 N2 180.0 2_646 4_565 ?
N3 Cu1 N1 104.87(10) . 3_656 ?
N3 Cu1 N1 75.13(10) 3_656 3_656 ?
N2 Cu1 N1 92.95(10) 2_646 3_656 ?
N2 Cu1 N1 87.05(10) 4_565 3_656 ?
N3 Cu1 N1 75.13(10) . . ?
N3 Cu1 N1 104.87(10) 3_656 . ?
N2 Cu1 N1 87.05(10) 2_646 . ?
N2 Cu1 N1 92.95(10) 4_565 . ?
N1 Cu1 N1 180.00(10) 3_656 . ?
C1 N1 C5 117.7(3) . . ?
C1 N1 Cu1 131.7(2) . . ?
C5 N1 Cu1 110.4(2) . . ?
C12 N2 C13 117.5(3) . . ?
C12 N2 Cu1 119.4(2) . 2_656 ?
C13 N2 Cu1 123.1(2) . 2_656 ?
C6 N3 N5 110.2(2) . . ?
C6 N3 Cu1 120.7(2) . . ?
N5 N3 Cu1 129.09(19) . . ?
C6 N4 C7 106.0(2) . . ?
C6 N4 N6 125.9(3) . . ?
C7 N4 N6 128.0(3) . . ?
C7 N5 N3 105.2(2) . . ?
N4 N6 H6B 109.3 . . ?
N4 N6 H6A 109.0 . . ?
H6B N6 H6A 106.8 . . ?
O3 S1 O1 115.23(17) . . ?
O3 S1 O2 113.8(2) . . ?
O1 S1 O2 115.5(2) . . ?
O3 S1 C14 104.6(2) . . ?
O1 S1 C14 103.1(2) . . ?
O2 S1 C14 102.3(2) . . ?
C7 S2 C8 100.02(16) . . ?

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
N1 C1 C2 C3 -0.7(6) . . . . ?
C1 C2 C3 C4 0.8(6) . . . . ?
C2 C3 C4 C5 -1.1(6) . . . . ?
C3 C4 C5 N1 1.4(5) . . . . ?
C3 C4 C5 C6 180.0(3) . . . . ?
N1 C5 C6 N3 3.6(4) . . . . ?
C4 C5 C6 N3 -175.2(3) . . . . ?
N1 C5 C6 N4 -175.0(3) . . . . ?
C4 C5 C6 N4 6.2(6) . . . . ?
S2 C8 C9 C13 -106.7(3) . . . . ?
S2 C8 C9 C10 73.6(4) . . . . ?
C13 C9 C10 C11 1.9(5) . . . . ?
C8 C9 C10 C11 -178.4(3) . . . . ?
C9 C10 C11 C12 0.1(6) . . . . ?
C10 C11 C12 N2 -2.0(6) . . . . ?
C10 C9 C13 N2 -2.3(5) . . . . ?
C8 C9 C13 N2 178.0(3) . . . . ?
C2 C1 N1 C5 0.9(6) . . . . ?
C2 C1 N1 Cu1 -173.0(3) . . . . ?
C4 C5 N1 C1 -1.2(5) . . . . ?
C6 C5 N1 C1 180.0(3) . . . . ?
C4 C5 N1 Cu1 173.9(3) . . . . ?
C6 C5 N1 Cu1 -4.9(3) . . . . ?
N3 Cu1 N1 C1 178.3(4) . . . . ?
N3 Cu1 N1 C1 -1.7(4) 3_656 . . . ?
N2 Cu1 N1 C1 88.2(3) 2_646 . . . ?
N2 Cu1 N1 C1 -91.8(3) 4_565 . . . ?
N1 Cu1 N1 C1 -26(100) 3_656 . . . ?
N3 Cu1 N1 C5 4.1(2) . . . . ?
N3 Cu1 N1 C5 -175.9(2) 3_656 . . . ?
N2 Cu1 N1 C5 -86.0(2) 2_646 . . . ?
N2 Cu1 N1 C5 94.0(2) 4_565 . . . ?
N1 Cu1 N1 C5 160(100) 3_656 . . . ?
C11 C12 N2 C13 1.7(5) . . . . ?
C11 C12 N2 Cu1 -176.6(3) . . . 2_656 ?
C9 C13 N2 C12 0.5(5) . . . . ?
C9 C13 N2 Cu1 178.7(2) . . . 2_656 ?
N4 C6 N3 N5 -0.8(3) . . . . ?
C5 C6 N3 N5 -179.7(3) . . . . ?
N4 C6 N3 Cu1 179.21(19) . . . . ?
C5 C6 N3 Cu1 0.3(4) . . . . ?
N3 Cu1 N3 C6 -37(100) 3_656 . . . ?
N2 Cu1 N3 C6 84.8(2) 2_646 . . . ?
N2 Cu1 N3 C6 -95.2(2) 4_565 . . . ?
N1 Cu1 N3 C6 177.7(2) 3_656 . . . ?
N1 Cu1 N3 C6 -2.3(2) . . . . ?
N3 Cu1 N3 N5 143(100) 3_656 . . . ?
N2 Cu1 N3 N5 -95.2(3) 2_646 . . . ?
N2 Cu1 N3 N5 84.8(3) 4_565 . . . ?
N1 Cu1 N3 N5 -2.3(3) 3_656 . . . ?
N1 Cu1 N3 N5 177.7(3) . . . . ?
N3 C6 N4 C7 0.4(3) . . . . ?
C5 C6 N4 C7 179.2(3) . . . . ?
N3 C6 N4 N6 -179.8(3) . . . . ?
C5 C6 N4 N6 -1.0(5) . . . . ?
N5 C7 N4 C6 0.1(4) . . . . ?
S2 C7 N4 C6 179.3(2) . . . . ?
N5 C7 N4 N6 -179.7(3) . . . . ?
S2 C7 N4 N6 -0.5(5) . . . . ?
N4 C7 N5 N3 -0.6(4) . . . . ?
S2 C7 N5 N3 -179.7(3) . . . . ?
C6 N3 N5 C7 0.9(4) . . . . ?
Cu1 N3 N5 C7 -179.2(2) . . . . ?
F2 C14 S1 O3 -53.2(4) . . . . ?
F1 C14 S1 O3 -174.9(3) . . . . ?
F3 C14 S1 O3 66.9(4) . . . . ?
F2 C14 S1 O1 67.7(4) . . . . ?
F1 C14 S1 O1 -54.0(4) . . . . ?
F3 C14 S1 O1 -172.2(3) . . . . ?
F2 C14 S1 O2 -172.1(4) . . . . ?
F1 C14 S1 O2 66.2(4) . . . . ?
F3 C14 S1 O2 -51.9(4) . . . . ?
N5 C7 S2 C8 17.2(4) . . . . ?
N4 C7 S2 C8 -161.9(3) . . . . ?
C9 C8 S2 C7 -165.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6B O2 0.88 2.09 2.969(4) 170.8 4_665
N6 H6A O3 0.88 2.22 2.976(4) 144.3 1_655

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.066
_database_code_depnum_ccdc_archive 'CCDC 959230'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_exp_4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24 Cu F6 N12 O6 S4'
_chemical_formula_weight         930.37

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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 '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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   9.2121(8)
_cell_length_b                   18.8386(13)
_cell_length_c                   10.4187(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.408(9)
_cell_angle_gamma                90.00
_cell_volume                     1778.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1103
_cell_measurement_theta_min      2.4894
_cell_measurement_theta_max      28.4968

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             942
_exptl_absorpt_coefficient_mu    0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7587
_exptl_absorpt_correction_T_max  0.9284
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         7678
_diffrn_standards_interval_count 0.3
_diffrn_standards_interval_time  5
_diffrn_standards_decay_%        none
_diffrn_reflns_number            6606
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0783
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3312
_reflns_number_gt                2247
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0223P)^2^+0.9129P] where P=(Fo^2^+2Fc^2^)/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         3312
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
C1 C 0.6777(5) -0.1143(2) 0.3253(4) 0.0441(12) Uani 1 1 d . . .
H1 H 0.5995 -0.1456 0.3245 0.053 Uiso 1 1 calc R . .
C2 C 0.7976(6) -0.1358(2) 0.2705(4) 0.0512(13) Uani 1 1 d . . .
H2 H 0.7997 -0.1811 0.2355 0.061 Uiso 1 1 calc R . .
C3 C 0.9117(5) -0.0902(2) 0.2685(4) 0.0441(12) Uani 1 1 d . . .
H3 H 0.9914 -0.1035 0.2305 0.053 Uiso 1 1 calc R . .
C4 C 0.9072(5) -0.0233(2) 0.3244(4) 0.0360(11) Uani 1 1 d . . .
H4 H 0.9847 0.0085 0.3261 0.043 Uiso 1 1 calc R . .
C5 C 0.7854(4) -0.0054(2) 0.3770(4) 0.0263(9) Uani 1 1 d . . .
C6 C 0.7634(4) 0.06296(19) 0.4382(4) 0.0234(9) Uani 1 1 d . . .
C7 C 0.7745(4) 0.1709(2) 0.5154(4) 0.0268(9) Uani 1 1 d . . .
C8 C 0.7434(5) 0.2793(2) 0.6799(4) 0.0398(11) Uani 1 1 d . . .
H8A H 0.6402 0.2665 0.6548 0.048 Uiso 1 1 calc R . .
H8B H 0.7840 0.2543 0.7597 0.048 Uiso 1 1 calc R . .
C9 C 0.7584(4) 0.3588(2) 0.7011(4) 0.0319(10) Uani 1 1 d . . .
C10 C 0.6824(5) 0.4052(2) 0.6115(4) 0.0408(11) Uani 1 1 d . . .
H10 H 0.6198 0.3882 0.5378 0.049 Uiso 1 1 calc R . .
C11 C 0.6998(5) 0.4771(2) 0.6321(4) 0.0443(12) Uani 1 1 d . . .
H11 H 0.6479 0.5093 0.5733 0.053 Uiso 1 1 calc R . .
C12 C 0.7946(5) 0.5006(2) 0.7401(4) 0.0371(10) Uani 1 1 d . . .
H12 H 0.8093 0.5492 0.7511 0.045 Uiso 1 1 calc R . .
C13 C 0.8472(4) 0.3868(2) 0.8100(4) 0.0327(10) Uani 1 1 d . . .
H13 H 0.8960 0.3557 0.8726 0.039 Uiso 1 1 calc R . .
C14 C 0.1659(6) 0.3732(3) 0.5732(6) 0.0600(15) Uani 1 1 d . . .
Cu1 Cu 0.5000 0.0000 0.5000 0.02474(19) Uani 1 2 d S . .
F1 F 0.2384(4) 0.43325(16) 0.6111(3) 0.0886(11) Uani 1 1 d . . .
F2 F 0.0559(4) 0.38976(19) 0.4769(4) 0.0917(11) Uani 1 1 d . . .
F3 F 0.1060(3) 0.35198(19) 0.6726(3) 0.0869(11) Uani 1 1 d . . .
N1 N 0.6710(4) -0.05040(17) 0.3787(3) 0.0323(8) Uani 1 1 d . . .
N2 N 0.8668(3) 0.45710(17) 0.8304(3) 0.0298(8) Uani 1 1 d . . .
N3 N 0.6494(3) 0.07439(16) 0.4949(3) 0.0246(7) Uani 1 1 d . . .
N4 N 0.8457(3) 0.12342(16) 0.4488(3) 0.0275(8) Uani 1 1 d . . .
N5 N 0.6547(3) 0.14255(16) 0.5452(3) 0.0295(8) Uani 1 1 d . . .
N6 N 0.9785(3) 0.13320(17) 0.4014(3) 0.0359(9) Uani 1 1 d . . .
H6B H 0.9598 0.1579 0.3285 0.043 Uiso 1 1 d R . .
H6A H 1.0393 0.1586 0.4573 0.043 Uiso 1 1 d R . .
O1 O 0.3573(4) 0.34359(19) 0.4324(3) 0.0676(11) Uani 1 1 d . . .
O2 O 0.3841(4) 0.2926(2) 0.6496(3) 0.0693(11) Uani 1 1 d . . .
O3 O 0.1935(4) 0.24971(17) 0.4763(3) 0.0588(10) Uani 1 1 d . . .
S1 S 0.28914(14) 0.30750(7) 0.52684(12) 0.0468(3) Uani 1 1 d . . .
S2 S 0.84362(13) 0.25558(6) 0.55132(12) 0.0432(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.051(3) 0.026(2) 0.050(3) -0.002(2) -0.004(2) -0.007(2)
C2 0.073(4) 0.031(3) 0.048(3) -0.011(2) 0.007(3) 0.004(3)
C3 0.055(3) 0.040(3) 0.040(3) 0.001(2) 0.017(2) 0.012(3)
C4 0.039(2) 0.036(3) 0.034(3) -0.002(2) 0.010(2) 0.002(2)
C5 0.033(2) 0.021(2) 0.024(2) 0.0028(18) 0.0031(17) 0.0049(19)
C6 0.025(2) 0.019(2) 0.024(2) 0.0039(18) -0.0011(17) -0.0044(18)
C7 0.030(2) 0.022(2) 0.028(2) -0.0017(19) 0.0030(18) -0.0053(19)
C8 0.050(3) 0.030(2) 0.041(3) -0.001(2) 0.015(2) -0.009(2)
C9 0.030(2) 0.029(2) 0.039(3) -0.001(2) 0.012(2) -0.003(2)
C10 0.044(3) 0.043(3) 0.033(3) -0.009(2) 0.000(2) -0.003(2)
C11 0.051(3) 0.037(3) 0.040(3) 0.000(2) -0.005(2) 0.007(2)
C12 0.044(3) 0.023(2) 0.044(3) 0.000(2) 0.007(2) 0.007(2)
C13 0.035(2) 0.028(2) 0.037(3) 0.003(2) 0.011(2) 0.005(2)
C14 0.058(4) 0.057(4) 0.065(4) -0.017(3) 0.011(3) -0.014(3)
Cu1 0.0251(4) 0.0176(3) 0.0315(4) 0.0020(3) 0.0051(3) -0.0044(3)
F1 0.106(3) 0.061(2) 0.105(3) -0.044(2) 0.035(2) -0.037(2)
F2 0.076(2) 0.084(3) 0.107(3) -0.007(2) -0.004(2) 0.012(2)
F3 0.075(2) 0.116(3) 0.082(2) -0.039(2) 0.046(2) -0.029(2)
N1 0.0341(19) 0.0219(18) 0.038(2) -0.0004(17) -0.0019(16) -0.0051(17)
N2 0.0331(19) 0.0211(18) 0.036(2) -0.0002(17) 0.0075(16) 0.0022(16)
N3 0.0244(17) 0.0183(17) 0.0310(19) 0.0007(15) 0.0044(15) -0.0020(15)
N4 0.0276(18) 0.0240(18) 0.031(2) -0.0025(16) 0.0048(15) -0.0065(16)
N5 0.0290(18) 0.0202(18) 0.040(2) -0.0033(16) 0.0089(16) -0.0040(15)
N6 0.0302(19) 0.037(2) 0.042(2) -0.0015(18) 0.0130(17) -0.0116(17)
O1 0.079(2) 0.072(3) 0.062(2) -0.016(2) 0.037(2) -0.037(2)
O2 0.062(2) 0.078(3) 0.061(2) -0.009(2) -0.0083(19) 0.000(2)
O3 0.070(2) 0.052(2) 0.060(2) -0.0223(18) 0.0250(19) -0.0338(19)
S1 0.0464(7) 0.0507(8) 0.0459(8) -0.0121(6) 0.0148(6) -0.0180(6)
S2 0.0508(7) 0.0246(6) 0.0602(8) -0.0115(6) 0.0261(6) -0.0153(6)

_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
C1 N1 1.332(5) . ?
C1 C2 1.392(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.361(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(5) . ?
C4 H4 0.9300 . ?
C5 N1 1.355(5) . ?
C5 C6 1.468(5) . ?
C6 N3 1.313(4) . ?
C6 N4 1.362(4) . ?
C7 N5 1.312(4) . ?
C7 N4 1.369(4) . ?
C7 S2 1.734(4) . ?
C8 C9 1.515(6) . ?
C8 S2 1.815(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.375(6) . ?
C9 C13 1.379(6) . ?
C10 C11 1.376(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(6) . ?
C11 H11 0.9300 . ?
C12 N2 1.331(5) . ?
C12 H12 0.9300 . ?
C13 N2 1.348(5) . ?
C13 H13 0.9300 . ?
C14 F3 1.321(6) . ?
C14 F2 1.328(6) . ?
C14 F1 1.336(5) . ?
C14 S1 1.803(5) . ?
Cu1 N3 1.972(3) 3_656 ?
Cu1 N3 1.972(3) . ?
Cu1 N2 2.121(3) 4_565 ?
Cu1 N2 2.121(3) 2_646 ?
Cu1 N1 2.387(3) . ?
Cu1 N1 2.387(3) 3_656 ?
N2 Cu1 2.121(3) 2_656 ?
N3 N5 1.384(4) . ?
N4 N6 1.412(4) . ?
N6 H6B 0.8808 . ?
N6 H6A 0.8739 . ?
O1 S1 1.431(3) . ?
O2 S1 1.441(4) . ?
O3 S1 1.439(3) . ?

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
N1 C1 C2 122.4(4) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 119.0(4) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 118.4(4) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
N1 C5 C4 123.0(4) . . ?
N1 C5 C6 112.0(3) . . ?
C4 C5 C6 125.0(4) . . ?
N3 C6 N4 107.8(3) . . ?
N3 C6 C5 121.6(3) . . ?
N4 C6 C5 130.6(3) . . ?
N5 C7 N4 110.8(3) . . ?
N5 C7 S2 128.0(3) . . ?
N4 C7 S2 121.3(3) . . ?
C9 C8 S2 107.8(3) . . ?
C9 C8 H8A 110.1 . . ?
S2 C8 H8A 110.1 . . ?
C9 C8 H8B 110.1 . . ?
S2 C8 H8B 110.1 . . ?
H8A C8 H8B 108.5 . . ?
C10 C9 C13 117.9(4) . . ?
C10 C9 C8 120.6(4) . . ?
C13 C9 C8 121.5(4) . . ?
C9 C10 C11 119.4(4) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 119.0(4) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
N2 C12 C11 123.1(4) . . ?
N2 C12 H12 118.5 . . ?
C11 C12 H12 118.5 . . ?
N2 C13 C9 123.3(4) . . ?
N2 C13 H13 118.4 . . ?
C9 C13 H13 118.4 . . ?
F3 C14 F2 107.0(4) . . ?
F3 C14 F1 106.4(4) . . ?
F2 C14 F1 107.3(5) . . ?
F3 C14 S1 112.0(4) . . ?
F2 C14 S1 113.0(4) . . ?
F1 C14 S1 110.8(4) . . ?
N3 Cu1 N3 180.00(12) 3_656 . ?
N3 Cu1 N2 89.52(12) 3_656 4_565 ?
N3 Cu1 N2 90.48(12) . 4_565 ?
N3 Cu1 N2 90.48(12) 3_656 2_646 ?
N3 Cu1 N2 89.52(12) . 2_646 ?
N2 Cu1 N2 180.00(12) 4_565 2_646 ?
N3 Cu1 N1 105.19(11) 3_656 . ?
N3 Cu1 N1 74.81(11) . . ?
N2 Cu1 N1 92.77(11) 4_565 . ?
N2 Cu1 N1 87.23(11) 2_646 . ?
N3 Cu1 N1 74.81(11) 3_656 3_656 ?
N3 Cu1 N1 105.19(11) . 3_656 ?
N2 Cu1 N1 87.23(11) 4_565 3_656 ?
N2 Cu1 N1 92.77(11) 2_646 3_656 ?
N1 Cu1 N1 180.000(1) . 3_656 ?
C1 N1 C5 117.6(3) . . ?
C1 N1 Cu1 131.7(3) . . ?
C5 N1 Cu1 110.4(2) . . ?
C12 N2 C13 117.2(4) . . ?
C12 N2 Cu1 119.6(3) . 2_656 ?
C13 N2 Cu1 123.1(3) . 2_656 ?
C6 N3 N5 110.2(3) . . ?
C6 N3 Cu1 121.0(2) . . ?
N5 N3 Cu1 128.8(2) . . ?
C6 N4 C7 106.1(3) . . ?
C6 N4 N6 125.8(3) . . ?
C7 N4 N6 128.1(3) . . ?
C7 N5 N3 105.2(3) . . ?
N4 N6 H6B 108.9 . . ?
N4 N6 H6A 109.2 . . ?
H6B N6 H6A 106.7 . . ?
O1 S1 O3 115.1(2) . . ?
O1 S1 O2 115.6(2) . . ?
O3 S1 O2 114.2(2) . . ?
O1 S1 C14 103.5(2) . . ?
O3 S1 C14 104.1(2) . . ?
O2 S1 C14 101.9(3) . . ?
C7 S2 C8 99.79(18) . . ?

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
N1 C1 C2 C3 -1.2(7) . . . . ?
C1 C2 C3 C4 1.5(7) . . . . ?
C2 C3 C4 C5 -1.4(7) . . . . ?
C3 C4 C5 N1 1.1(6) . . . . ?
C3 C4 C5 C6 -179.4(4) . . . . ?
N1 C5 C6 N3 4.6(5) . . . . ?
C4 C5 C6 N3 -174.9(4) . . . . ?
N1 C5 C6 N4 -175.1(4) . . . . ?
C4 C5 C6 N4 5.4(7) . . . . ?
S2 C8 C9 C10 73.3(4) . . . . ?
S2 C8 C9 C13 -107.0(4) . . . . ?
C13 C9 C10 C11 1.3(6) . . . . ?
C8 C9 C10 C11 -178.9(4) . . . . ?
C9 C10 C11 C12 1.2(6) . . . . ?
C10 C11 C12 N2 -3.1(6) . . . . ?
C10 C9 C13 N2 -2.4(6) . . . . ?
C8 C9 C13 N2 177.9(3) . . . . ?
C2 C1 N1 C5 0.9(6) . . . . ?
C2 C1 N1 Cu1 -172.5(3) . . . . ?
C4 C5 N1 C1 -0.8(6) . . . . ?
C6 C5 N1 C1 179.7(4) . . . . ?
C4 C5 N1 Cu1 173.9(3) . . . . ?
C6 C5 N1 Cu1 -5.6(4) . . . . ?
N3 Cu1 N1 C1 -1.8(4) 3_656 . . . ?
N3 Cu1 N1 C1 178.2(4) . . . . ?
N2 Cu1 N1 C1 -92.1(4) 4_565 . . . ?
N2 Cu1 N1 C1 87.9(4) 2_646 . . . ?
N1 Cu1 N1 C1 156(100) 3_656 . . . ?
N3 Cu1 N1 C5 -175.6(2) 3_656 . . . ?
N3 Cu1 N1 C5 4.4(2) . . . . ?
N2 Cu1 N1 C5 94.2(3) 4_565 . . . ?
N2 Cu1 N1 C5 -85.8(3) 2_646 . . . ?
N1 Cu1 N1 C5 -18(100) 3_656 . . . ?
C11 C12 N2 C13 2.1(6) . . . . ?
C11 C12 N2 Cu1 -176.0(3) . . . 2_656 ?
C9 C13 N2 C12 0.7(5) . . . . ?
C9 C13 N2 Cu1 178.7(3) . . . 2_656 ?
N4 C6 N3 N5 -0.5(4) . . . . ?
C5 C6 N3 N5 179.7(3) . . . . ?
N4 C6 N3 Cu1 179.4(2) . . . . ?
C5 C6 N3 Cu1 -0.4(5) . . . . ?
N3 Cu1 N3 C6 -151(50) 3_656 . . . ?
N2 Cu1 N3 C6 -94.9(3) 4_565 . . . ?
N2 Cu1 N3 C6 85.1(3) 2_646 . . . ?
N1 Cu1 N3 C6 -2.1(3) . . . . ?
N1 Cu1 N3 C6 177.9(3) 3_656 . . . ?
N3 Cu1 N3 N5 28(50) 3_656 . . . ?
N2 Cu1 N3 N5 85.0(3) 4_565 . . . ?
N2 Cu1 N3 N5 -95.0(3) 2_646 . . . ?
N1 Cu1 N3 N5 177.8(3) . . . . ?
N1 Cu1 N3 N5 -2.2(3) 3_656 . . . ?
N3 C6 N4 C7 0.3(4) . . . . ?
C5 C6 N4 C7 -179.9(4) . . . . ?
N3 C6 N4 N6 179.5(3) . . . . ?
C5 C6 N4 N6 -0.8(6) . . . . ?
N5 C7 N4 C6 0.0(4) . . . . ?
S2 C7 N4 C6 179.6(3) . . . . ?
N5 C7 N4 N6 -179.2(3) . . . . ?
S2 C7 N4 N6 0.5(6) . . . . ?
N4 C7 N5 N3 -0.3(4) . . . . ?
S2 C7 N5 N3 -179.9(3) . . . . ?
C6 N3 N5 C7 0.5(4) . . . . ?
Cu1 N3 N5 C7 -179.4(3) . . . . ?
F3 C14 S1 O1 -172.2(4) . . . . ?
F2 C14 S1 O1 66.8(4) . . . . ?
F1 C14 S1 O1 -53.6(5) . . . . ?
F3 C14 S1 O3 67.2(4) . . . . ?
F2 C14 S1 O3 -53.8(4) . . . . ?
F1 C14 S1 O3 -174.2(4) . . . . ?
F3 C14 S1 O2 -51.9(4) . . . . ?
F2 C14 S1 O2 -172.9(4) . . . . ?
F1 C14 S1 O2 66.7(4) . . . . ?
N5 C7 S2 C8 17.6(4) . . . . ?
N4 C7 S2 C8 -161.9(3) . . . . ?
C9 C8 S2 C7 -165.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6A O3 0.87 2.21 2.965(4) 143.9 1_655
N6 H6B O2 0.88 2.09 2.961(5) 170.9 4_665

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.078

_database_code_depnum_ccdc_archive 'CCDC 959231'