# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

#######################################################################
#
#                 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_Complex_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H26 Cu2 N6 O8'
_chemical_formula_sum            'C28 H26 Cu2 N6 O8'
_chemical_formula_weight         702.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   8.2841(4)
_cell_length_b                   8.9822(4)
_cell_length_c                   9.6248(4)
_cell_angle_alpha                86.725(3)
_cell_angle_beta                 82.846(2)
_cell_angle_gamma                81.578(2)
_cell_volume                     702.39(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5745
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      27.67

_exptl_crystal_description       flakes
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             358
_exptl_absorpt_coefficient_mu    1.577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.868
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_process_details   multi-scan

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3221
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0044
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         27.45
_reflns_number_total             3221
_reflns_number_gt                3218
_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)+(0.1000P)²+0.0110P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3221
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0131
_refine_ls_R_factor_gt           0.0130
_refine_ls_wR_factor_ref         0.1082
_refine_ls_wR_factor_gt          0.1081
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_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 0.654525(14) 1.000057(13) 0.384783(12) 0.03494(11) Uani 1 1 d . . .
O1 O 0.59170(14) 1.12503(13) 0.54078(12) 0.0413(2) Uani 1 1 d . . .
O2 O 0.53125(15) 1.15541(13) 0.26660(13) 0.0451(3) Uani 1 1 d . . .
O3 O 0.76184(15) 1.24426(15) 0.25601(17) 0.0671(4) Uani 1 1 d . . .
O4 O 0.5481(2) 1.37992(14) 0.18363(18) 0.0718(4) Uani 1 1 d . . .
N1 N 0.72191(16) 0.85556(15) 0.23398(14) 0.0380(3) Uani 1 1 d . . .
N2 N 0.79974(15) 0.85638(14) 0.48563(14) 0.0363(2) Uani 1 1 d . . .
N3 N 0.61557(16) 1.26386(13) 0.23409(13) 0.0462(3) Uani 1 1 d . . .
C1 C 0.6792(2) 0.8739(2) 0.10257(16) 0.0478(3) Uani 1 1 d . . .
H1 H 0.6230 0.9659 0.0748 0.057 Uiso 1 1 calc R . .
C2 C 0.7160(2) 0.7609(2) 0.00870(17) 0.0567(4) Uani 1 1 d . . .
H2 H 0.6872 0.7768 -0.0819 0.068 Uiso 1 1 calc R . .
C3 C 0.7955(2) 0.6246(2) 0.0506(2) 0.0627(4) Uani 1 1 d . . .
H3 H 0.8188 0.5456 -0.0104 0.075 Uiso 1 1 calc R . .
C4 C 0.8412(2) 0.60529(18) 0.1850(2) 0.0570(4) Uani 1 1 d . . .
H4 H 0.8971 0.5138 0.2144 0.068 Uiso 1 1 calc R . .
C5 C 0.80304(17) 0.72314(15) 0.27455(15) 0.0415(3) Uani 1 1 d . . .
C6 C 0.84728(17) 0.70911(15) 0.42327(16) 0.0445(3) Uani 1 1 d . . .
H6 H 0.9662 0.6800 0.4215 0.053 Uiso 1 1 calc R . .
C8 C 0.85889(15) 0.88505(16) 0.59724(14) 0.0409(3) Uani 1 1 d . . .
H8 H 0.9386 0.8124 0.6302 0.049 Uiso 1 1 calc R . .
C9 C 0.81269(15) 1.01900(15) 0.67488(12) 0.0378(3) Uani 1 1 d . . .
C10 C 0.89504(18) 1.0342(2) 0.79227(15) 0.0498(3) Uani 1 1 d . . .
H10 H 0.9798 0.9597 0.8133 0.060 Uiso 1 1 calc R . .
C11 C 0.8541(2) 1.1544(2) 0.87529(16) 0.0572(4) Uani 1 1 d . . .
H11 H 0.9092 1.1617 0.9526 0.069 Uiso 1 1 calc R . .
C12 C 0.7279(2) 1.2670(2) 0.84282(17) 0.0541(4) Uani 1 1 d . . .
H12 H 0.6991 1.3496 0.8992 0.065 Uiso 1 1 calc R . .
C13 C 0.64524(19) 1.25766(18) 0.72847(17) 0.0467(3) Uani 1 1 d . . .
H13 H 0.5634 1.3352 0.7075 0.056 Uiso 1 1 calc R . .
C14 C 0.68307(16) 1.13274(15) 0.64361(14) 0.0364(3) Uani 1 1 d . . .
C7 C 0.7584(3) 0.59099(19) 0.5094(2) 0.0641(5) Uani 1 1 d . . .
H7A H 0.7920 0.5804 0.6018 0.096 Uiso 1 1 calc R . .
H7B H 0.7854 0.4962 0.4649 0.096 Uiso 1 1 calc R . .
H7C H 0.6419 0.6221 0.5158 0.096 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 O1 1.9005(11) . ?
Cu1 N2 1.9359(13) . ?
Cu1 N1 1.9759(14) . ?
Cu1 O2 1.9936(12) . ?
O1 C14 1.3293(17) . ?
O2 N3 1.2825(16) . ?
O3 N3 1.2413(19) . ?
O4 N3 1.2142(18) . ?
N1 C5 1.340(2) . ?
N1 C1 1.350(2) . ?
N2 C8 1.2884(19) . ?
N2 C6 1.4644(18) . ?
C1 C2 1.373(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.367(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.515(2) . ?
C6 C7 1.527(2) . ?
C6 H6 0.9800 . ?
C8 C9 1.4314(19) . ?
C8 H8 0.9300 . ?
C9 C10 1.4134(17) . ?
C9 C14 1.418(2) . ?
C10 C11 1.358(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.395(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.401(2) . ?
C13 H13 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N2 93.23(5) . . ?
O1 Cu1 N1 175.18(4) . . ?
N2 Cu1 N1 82.66(6) . . ?
O1 Cu1 O2 89.32(5) . . ?
N2 Cu1 O2 172.58(4) . . ?
N1 Cu1 O2 95.07(5) . . ?
C14 O1 Cu1 124.64(10) . . ?
N3 O2 Cu1 109.45(9) . . ?
C5 N1 C1 119.20(14) . . ?
C5 N1 Cu1 114.60(10) . . ?
C1 N1 Cu1 125.83(12) . . ?
C8 N2 C6 120.11(13) . . ?
C8 N2 Cu1 124.36(11) . . ?
C6 N2 Cu1 115.47(10) . . ?
O4 N3 O3 123.63(15) . . ?
O4 N3 O2 118.27(14) . . ?
O3 N3 O2 118.10(13) . . ?
N1 C1 C2 122.08(17) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 118.92(17) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.34(16) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 119.37(17) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 121.06(15) . . ?
N1 C5 C6 116.82(12) . . ?
C4 C5 C6 122.10(15) . . ?
N2 C6 C5 108.05(11) . . ?
N2 C6 C7 110.05(13) . . ?
C5 C6 C7 110.79(14) . . ?
N2 C6 H6 109.3 . . ?
C5 C6 H6 109.3 . . ?
C7 C6 H6 109.3 . . ?
N2 C8 C9 125.70(12) . . ?
N2 C8 H8 117.2 . . ?
C9 C8 H8 117.2 . . ?
C10 C9 C14 118.79(13) . . ?
C10 C9 C8 118.12(13) . . ?
C14 C9 C8 123.01(11) . . ?
C11 C10 C9 121.99(15) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C10 C11 C12 118.93(14) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C13 C12 C11 121.12(15) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 120.74(15) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
O1 C14 C13 118.03(13) . . ?
O1 C14 C9 123.54(12) . . ?
C13 C14 C9 118.39(12) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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 O1 C14 25.75(12) . . . . ?
O2 Cu1 O1 C14 -147.28(12) . . . . ?
O1 Cu1 O2 N3 77.30(10) . . . . ?
N1 Cu1 O2 N3 -104.71(10) . . . . ?
N2 Cu1 N1 C5 11.55(10) . . . . ?
O2 Cu1 N1 C5 -175.56(10) . . . . ?
N2 Cu1 N1 C1 -175.52(13) . . . . ?
O2 Cu1 N1 C1 -2.63(13) . . . . ?
O1 Cu1 N2 C8 -19.80(12) . . . . ?
N1 Cu1 N2 C8 162.74(12) . . . . ?
O1 Cu1 N2 C6 162.88(10) . . . . ?
N1 Cu1 N2 C6 -14.59(10) . . . . ?
Cu1 O2 N3 O4 -167.24(13) . . . . ?
Cu1 O2 N3 O3 12.75(17) . . . . ?
C5 N1 C1 C2 0.1(2) . . . . ?
Cu1 N1 C1 C2 -172.55(12) . . . . ?
N1 C1 C2 C3 1.3(2) . . . . ?
C1 C2 C3 C4 -1.9(3) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C1 N1 C5 C4 -0.9(2) . . . . ?
Cu1 N1 C5 C4 172.52(11) . . . . ?
C1 N1 C5 C6 -179.83(12) . . . . ?
Cu1 N1 C5 C6 -6.39(15) . . . . ?
C3 C4 C5 N1 0.3(2) . . . . ?
C3 C4 C5 C6 179.18(14) . . . . ?
C8 N2 C6 C5 -163.04(12) . . . . ?
Cu1 N2 C6 C5 14.40(14) . . . . ?
C8 N2 C6 C7 75.86(18) . . . . ?
Cu1 N2 C6 C7 -106.69(14) . . . . ?
N1 C5 C6 N2 -4.94(16) . . . . ?
C4 C5 C6 N2 176.16(13) . . . . ?
N1 C5 C6 C7 115.69(14) . . . . ?
C4 C5 C6 C7 -63.21(18) . . . . ?
C6 N2 C8 C9 -174.60(12) . . . . ?
Cu1 N2 C8 C9 8.19(19) . . . . ?
N2 C8 C9 C10 -177.61(13) . . . . ?
N2 C8 C9 C14 5.7(2) . . . . ?
C14 C9 C10 C11 -0.2(2) . . . . ?
C8 C9 C10 C11 -177.08(13) . . . . ?
C9 C10 C11 C12 -0.6(2) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
C11 C12 C13 C14 1.6(2) . . . . ?
Cu1 O1 C14 C13 161.90(11) . . . . ?
Cu1 O1 C14 C9 -20.38(18) . . . . ?
C12 C13 C14 O1 175.41(14) . . . . ?
C12 C13 C14 C9 -2.4(2) . . . . ?
C10 C9 C14 O1 -175.97(13) . . . . ?
C8 C9 C14 O1 0.7(2) . . . . ?
C10 C9 C14 C13 1.74(18) . . . . ?
C8 C9 C14 C13 178.42(12) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.021
_database_code_depnum_ccdc_archive 'CCDC 974876'
#######################################################################
#
#                 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_Complex_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 Cl Cu N2 O6'
_chemical_formula_sum            'C14 H15 Cl Cu N2 O6'
_chemical_formula_weight         406.28

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   23.672(2)
_cell_length_b                   8.6741(7)
_cell_length_c                   27.466(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 139.368(5)
_cell_angle_gamma                90.00
_cell_volume                     3672.5(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7182
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      23.65

_exptl_crystal_description       Flake
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1656.0
_exptl_absorpt_coefficient_mu    1.364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.570
_exptl_absorpt_correction_T_max  0.683
_exptl_absorpt_process_details   multi-scan

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4195
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0022
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         27.45
_reflns_number_total             4195
_reflns_number_gt                4193
_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)+(0.1300P)²+4.7182P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4195
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1845
_refine_ls_wR_factor_gt          0.1845
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.001
_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 0.08011(2) 0.73222(4) 1.02513(2) 0.05555(18) Uani 1 1 d . . .
Cl1 Cl 0.05815(7) 0.44426(11) 0.91326(6) 0.0756(3) Uani 1 1 d . . .
O1 O -0.04062(17) 0.7273(3) 0.95919(15) 0.0639(6) Uani 1 1 d . . .
O2 O 0.09614(14) 0.5645(3) 1.08467(12) 0.0616(5) Uani 1 1 d . . .
H3BO H 0.0831 0.4812 1.0639 0.092 Uiso 1 1 d R . .
H2AO H 0.0713 0.5857 1.0932 0.092 Uiso 1 1 d R . .
O3 O 0.0935(4) 0.5124(6) 0.9776(3) 0.1450(19) Uani 1 1 d . . .
O6 O 0.0478(4) 0.5454(11) 0.8695(4) 0.231(4) Uani 1 1 d . . .
O5 O 0.1116(4) 0.3342(8) 0.9276(4) 0.182(3) Uani 1 1 d . . .
O4 O -0.0205(3) 0.3680(5) 0.8741(3) 0.1243(15) Uani 1 1 d . . .
N1 N 0.2058(2) 0.7614(3) 1.09769(19) 0.0629(7) Uani 1 1 d . . .
N2 N 0.07249(18) 0.9084(3) 0.97713(15) 0.0591(6) Uani 1 1 d . . .
C1 C 0.2691(3) 0.6844(6) 1.1615(2) 0.0827(11) Uani 1 1 d . . .
H1 H 0.2540 0.5953 1.1721 0.099 Uiso 1 1 d R . .
C2 C 0.3551(3) 0.7201(8) 1.2129(4) 0.113(2) Uani 1 1 d . . .
H2 H 0.3977 0.6692 1.2585 0.136 Uiso 1 1 calc R . .
C3 C 0.3756(3) 0.8371(9) 1.1933(4) 0.121(2) Uani 1 1 d . . .
H3 H 0.4272 0.8796 1.2150 0.146 Uiso 1 1 d R . .
C4 C 0.3122(3) 0.9169(6) 1.1292(3) 0.0926(13) Uani 1 1 d . . .
H4 H 0.3261 0.9988 1.1179 0.111 Uiso 1 1 calc R . .
C5 C 0.2268(2) 0.8767(4) 1.0805(2) 0.0697(9) Uani 1 1 d . . .
C6 C 0.1545(3) 0.9563(4) 1.0083(2) 0.0672(8) Uani 1 1 d . . .
H6 H 0.1615 1.0678 1.0171 0.081 Uiso 1 1 calc R . .
C7 C 0.1551(4) 0.9200(7) 0.9549(3) 0.1007(15) Uani 1 1 d . . .
H7A H 0.2099 0.9497 0.9770 0.151 Uiso 1 1 calc R . .
H7B H 0.1093 0.9757 0.9091 0.151 Uiso 1 1 calc R . .
H7C H 0.1465 0.8113 0.9447 0.151 Uiso 1 1 calc R . .
C8 C 0.0038(3) 0.9841(4) 0.9238(2) 0.0658(8) Uani 1 1 d . . .
H8 H 0.0095 1.0711 0.9079 0.079 Uiso 1 1 calc R . .
C9 C -0.0819(2) 0.9495(4) 0.88523(19) 0.0628(7) Uani 1 1 d . . .
C10 C -0.1518(3) 1.0447(5) 0.8241(2) 0.0821(11) Uani 1 1 d . . .
H10 H -0.1403 1.1282 0.8114 0.099 Uiso 1 1 calc R . .
C11 C -0.2359(3) 1.0171(6) 0.7830(2) 0.0850(12) Uani 1 1 d . . .
H11 H -0.2811 1.0789 0.7424 0.102 Uiso 1 1 calc R . .
C12 C -0.2516(3) 0.8960(5) 0.8036(2) 0.0795(11) Uani 1 1 d . . .
H12 H -0.3082 0.8775 0.7768 0.095 Uiso 1 1 calc R . .
C13 C -0.1863(2) 0.8011(5) 0.8624(2) 0.0698(8) Uani 1 1 d . . .
H13 H -0.1997 0.7205 0.8747 0.084 Uiso 1 1 calc R . .
C14 C -0.1008(2) 0.8228(4) 0.90406(17) 0.0567(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.896(3) . ?
Cu1 N2 1.935(3) . ?
Cu1 N1 1.971(3) . ?
Cu1 O2 1.999(2) . ?
Cl1 O6 1.353(6) . ?
Cl1 O5 1.383(5) . ?
Cl1 O3 1.389(4) . ?
Cl1 O4 1.422(8) . ?
O1 C14 1.317(4) . ?
O2 H3BO 0.8212 . ?
O2 H2AO 0.8027 . ?
N1 C1 1.333(6) . ?
N1 C5 1.351(5) . ?
N2 C8 1.267(5) . ?
N2 C6 1.467(9) . ?
C1 C2 1.367(6) . ?
C1 H1 0.9845 . ?
C2 C3 1.396(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.349(9) . ?
C3 H3 0.9377 . ?
C4 C5 1.376(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.479(6) . ?
C6 C7 1.510(11) . ?
C6 H6 0.9800 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.437(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.422(5) . ?
C9 C14 1.425(5) . ?
C10 C11 1.374(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(5) . ?
C13 H13 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
O1 Cu1 N2 94.21(11) . . ?
O1 Cu1 N1 173.18(12) . . ?
N2 Cu1 N1 82.91(13) . . ?
O1 Cu1 O2 88.71(10) . . ?
N2 Cu1 O2 173.76(10) . . ?
N1 Cu1 O2 93.58(11) . . ?
O6 Cl1 O5 102.1(5) . . ?
O6 Cl1 O3 112.5(5) . . ?
O5 Cl1 O3 113.2(4) . . ?
O6 Cl1 O4 112.4(4) . . ?
O5 Cl1 O4 106.5(4) . . ?
O3 Cl1 O4 109.8(3) . . ?
C14 O1 Cu1 128.0(2) . . ?
Cu1 O2 H3BO 109.6 . . ?
Cu1 O2 H2AO 110.2 . . ?
H3BO O2 H2AO 115.5 . . ?
C1 N1 C5 119.0(3) . . ?
C1 N1 Cu1 126.4(3) . . ?
C5 N1 Cu1 114.5(3) . . ?
C8 N2 C6 119.7(3) . . ?
C8 N2 Cu1 124.9(5) . . ?
C6 N2 Cu1 115.3(2) . . ?
N1 C1 C2 123.5(5) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 117.6 . . ?
C1 C2 C3 116.5(6) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 H2 121.7 . . ?
C4 C3 C2 120.5(9) . . ?
C4 C3 H3 104.5 . . ?
C2 C3 H3 135.0 . . ?
C3 C4 C5 119.8(5) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 120.5(4) . . ?
N1 C5 C6 117.2(3) . . ?
C4 C5 C6 122.4(4) . . ?
N2 C6 C5 108.8(3) . . ?
N2 C6 C7 110.9(3) . . ?
C5 C6 C7 110.6(4) . . ?
N2 C6 H6 108.8 . . ?
C5 C6 H6 108.8 . . ?
C7 C6 H6 108.8 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C9 126.7(3) . . ?
N2 C8 H8 116.6 . . ?
C9 C8 H8 116.6 . . ?
C10 C9 C14 118.1(4) . . ?
C10 C9 C8 118.5(3) . . ?
C14 C9 C8 123.4(3) . . ?
C11 C10 C9 122.1(4) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C10 C11 C12 118.2(4) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
C13 C12 C11 122.0(4) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C12 C13 C14 121.6(4) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
O1 C14 C13 119.4(3) . . ?
O1 C14 C9 122.6(3) . . ?
C13 C14 C9 118.0(3) . . ?

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

O2 Cu1 O1 C14 172.0(3) . . . . ?
N2 Cu1 N1 C1 174.5(4) . . . . ?
O2 Cu1 N1 C1 -0.4(4) . . . . ?
N2 Cu1 N1 C5 -2.2(3) . . . . ?
O2 Cu1 N1 C5 -177.1(3) . . . . ?
O1 Cu1 N2 C8 4.3(3) . . . . ?
N1 Cu1 N2 C8 -169.5(3) . . . . ?
O1 Cu1 N2 C6 -177.6(2) . . . . ?
N1 Cu1 N2 C6 8.6(2) . . . . ?
C5 N1 C1 C2 3.0(7) . . . . ?
Cu1 N1 C1 C2 -173.5(5) . . . . ?
N1 C1 C2 C3 -4.5(9) . . . . ?
C1 C2 C3 C4 4.9(10) . . . . ?
C2 C3 C4 C5 -3.9(9) . . . . ?
C1 N1 C5 C4 -1.8(6) . . . . ?
Cu1 N1 C5 C4 175.2(3) . . . . ?
C1 N1 C5 C6 178.4(4) . . . . ?
Cu1 N1 C5 C6 -4.6(4) . . . . ?
C3 C4 C5 N1 2.3(7) . . . . ?
C3 C4 C5 C6 -178.0(5) . . . . ?
C8 N2 C6 C5 165.6(3) . . . . ?
Cu1 N2 C6 C5 -12.6(3) . . . . ?
C8 N2 C6 C7 -72.5(4) . . . . ?
Cu1 N2 C6 C7 109.3(4) . . . . ?
N1 C5 C6 N2 11.0(4) . . . . ?
C4 C5 C6 N2 -168.8(4) . . . . ?
N1 C5 C6 C7 -111.1(4) . . . . ?
C4 C5 C6 C7 69.1(5) . . . . ?
C6 N2 C8 C9 177.5(3) . . . . ?
Cu1 N2 C8 C9 -4.5(5) . . . . ?
N2 C8 C9 C10 -177.0(3) . . . . ?
N2 C8 C9 C14 1.6(5) . . . . ?
C14 C9 C10 C11 -0.4(6) . . . . ?
C8 C9 C10 C11 178.3(4) . . . . ?
C9 C10 C11 C12 1.7(6) . . . . ?
C10 C11 C12 C13 -1.3(6) . . . . ?
C11 C12 C13 C14 -0.3(6) . . . . ?
Cu1 O1 C14 C13 -179.0(2) . . . . ?
Cu1 O1 C14 C9 0.6(5) . . . . ?
C12 C13 C14 O1 -178.8(3) . . . . ?
C12 C13 C14 C9 1.5(5) . . . . ?
C10 C9 C14 O1 179.2(3) . . . . ?
C8 C9 C14 O1 0.6(5) . . . . ?
C10 C9 C14 C13 -1.1(5) . . . . ?
C8 C9 C14 C13 -179.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.112
_database_code_depnum_ccdc_archive 'CCDC 974877'
#######################################################################
#
#                 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_Complex_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H26 Cu2 N10 O2'
_chemical_formula_sum            'C28 H26 Cu2 N10 O2'
_chemical_formula_weight         661.69

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   20.0960(16)
_cell_length_b                   7.3459(5)
_cell_length_c                   23.542(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 127.245(6)
_cell_angle_gamma                90.00
_cell_volume                     2766.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5078
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      24.44

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1352
_exptl_absorpt_coefficient_mu    1.582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.510
_exptl_absorpt_correction_T_max  0.642
_exptl_absorpt_process_details   multi-scan

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17099
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         25.51
_reflns_number_total             2570
_reflns_number_gt                2113
_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)+(0.1000P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2570
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1383
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 0.04021(2) 0.79665(5) 0.04450(2) 0.0364(2) Uani 1 1 d . . .
O1 O 0.04874(15) 0.8682(4) 0.12583(13) 0.0472(6) Uani 1 1 d . . .
N1 N 0.03655(19) 0.6926(3) -0.03609(16) 0.0400(7) Uani 1 1 d . . .
N2 N 0.14491(18) 0.6604(4) 0.10147(16) 0.0382(7) Uani 1 1 d . . .
N3 N -0.07652(17) 0.8905(4) -0.01887(15) 0.0412(7) Uani 1 1 d . . .
N4 N -0.11464(17) 0.9033(4) 0.00523(15) 0.0393(7) Uani 1 1 d . . .
N5 N -0.1540(2) 0.9180(5) 0.0254(2) 0.0604(9) Uani 1 1 d . . .
C1 C -0.0261(3) 0.7136(5) -0.1058(2) 0.0482(9) Uani 1 1 d . . .
H1 H -0.0735 0.7775 -0.1191 0.058 Uiso 1 1 calc R . .
C2 C -0.0228(3) 0.6447(6) -0.1579(2) 0.0545(10) Uani 1 1 d . . .
H2 H -0.0668 0.6626 -0.2059 0.065 Uiso 1 1 calc R . .
C3 C 0.0472(3) 0.5481(6) -0.1380(2) 0.0592(11) Uani 1 1 d . . .
H3 H 0.0506 0.4983 -0.1725 0.071 Uiso 1 1 calc R . .
C4 C 0.1123(3) 0.5257(5) -0.0664(2) 0.0527(10) Uani 1 1 d . . .
H4 H 0.1599 0.4612 -0.0522 0.063 Uiso 1 1 calc R . .
C5 C 0.1056(2) 0.6007(4) -0.01615(19) 0.0395(8) Uani 1 1 d . . .
C8 C 0.1866(2) 0.6236(5) 0.16873(19) 0.0415(8) Uani 1 1 d . . .
H8 H 0.2331 0.5488 0.1888 0.050 Uiso 1 1 calc R . .
C9 C 0.1681(2) 0.6868(4) 0.21510(18) 0.0384(8) Uani 1 1 d . . .
C10 C 0.2183(2) 0.6278(5) 0.2866(2) 0.0473(9) Uani 1 1 d . . .
H10 H 0.2637 0.5523 0.3027 0.057 Uiso 1 1 calc R . .
C11 C 0.2023(3) 0.6781(5) 0.3326(2) 0.0525(10) Uani 1 1 d . . .
H11 H 0.2353 0.6344 0.3791 0.063 Uiso 1 1 calc R . .
C12 C 0.1363(3) 0.7954(5) 0.3097(2) 0.0480(10) Uani 1 1 d . . .
H12 H 0.1255 0.8310 0.3413 0.058 Uiso 1 1 calc R . .
C13 C 0.0869(2) 0.8591(5) 0.24117(19) 0.0432(8) Uani 1 1 d . . .
H13 H 0.0438 0.9396 0.2273 0.052 Uiso 1 1 calc R . .
C14 C 0.0999(2) 0.8056(4) 0.19089(19) 0.0389(8) Uani 1 1 d . . .
C6 C 0.1749(2) 0.5846(5) 0.06255(19) 0.0415(8) Uani 1 1 d . . .
H6 H 0.1888 0.4558 0.0750 0.050 Uiso 1 1 calc R . .
C7 C 0.2528(3) 0.6867(5) 0.0834(2) 0.0520(10) Uani 1 1 d . . .
H7A H 0.2395 0.8129 0.0712 0.078 Uiso 1 1 calc R . .
H7B H 0.2724 0.6359 0.0584 0.078 Uiso 1 1 calc R . .
H7C H 0.2957 0.6754 0.1339 0.078 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 O1 1.891(2) . ?
Cu1 N2 1.952(3) . ?
Cu1 N3 1.992(3) . ?
Cu1 N1 2.005(3) . ?
O1 C14 1.307(4) . ?
N1 C1 1.342(5) . ?
N1 C5 1.347(4) . ?
N2 C8 1.295(4) . ?
N2 C6 1.477(4) . ?
N3 N4 1.202(4) . ?
N4 N5 1.148(4) . ?
C1 C2 1.366(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.380(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.504(5) . ?
C8 C9 1.426(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.408(5) . ?
C9 C14 1.421(5) . ?
C10 C11 1.354(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.414(5) . ?
C13 H13 0.9300 . ?
C6 C7 1.525(5) . ?
C6 H6 0.9800 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N2 92.71(11) . . ?
O1 Cu1 N3 90.35(11) . . ?
N2 Cu1 N3 169.40(12) . . ?
O1 Cu1 N1 173.31(11) . . ?
N2 Cu1 N1 82.06(12) . . ?
N3 Cu1 N1 94.08(12) . . ?
C14 O1 Cu1 127.8(2) . . ?
C1 N1 C5 119.3(3) . . ?
C1 N1 Cu1 125.7(3) . . ?
C5 N1 Cu1 114.9(2) . . ?
C8 N2 C6 118.4(3) . . ?
C8 N2 Cu1 125.3(2) . . ?
C6 N2 Cu1 116.2(2) . . ?
N4 N3 Cu1 118.2(2) . . ?
N5 N4 N3 177.1(3) . . ?
N1 C1 C2 122.4(4) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 118.6(4) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 119.6(4) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 119.1(4) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.0(3) . . ?
N1 C5 C6 117.3(3) . . ?
C4 C5 C6 121.7(3) . . ?
N2 C8 C9 126.4(3) . . ?
N2 C8 H8 116.8 . . ?
C9 C8 H8 116.8 . . ?
C10 C9 C14 119.2(3) . . ?
C10 C9 C8 119.0(3) . . ?
C14 C9 C8 121.8(3) . . ?
C11 C10 C9 121.7(4) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 119.5(4) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 121.5(4) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
O1 C14 C13 118.0(3) . . ?
O1 C14 C9 124.8(3) . . ?
C13 C14 C9 117.2(3) . . ?
N2 C6 C5 108.3(3) . . ?
N2 C6 C7 109.9(3) . . ?
C5 C6 C7 111.3(3) . . ?
N2 C6 H6 109.1 . . ?
C5 C6 H6 109.1 . . ?
C7 C6 H6 109.1 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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 O1 C14 -12.2(3) . . . . ?
N3 Cu1 O1 C14 157.7(3) . . . . ?
N2 Cu1 N1 C1 176.5(3) . . . . ?
N3 Cu1 N1 C1 6.5(3) . . . . ?
N2 Cu1 N1 C5 -6.2(2) . . . . ?
N3 Cu1 N1 C5 -176.3(2) . . . . ?
O1 Cu1 N2 C8 10.0(3) . . . . ?
N3 Cu1 N2 C8 -96.6(7) . . . . ?
N1 Cu1 N2 C8 -165.8(3) . . . . ?
O1 Cu1 N2 C6 -174.0(2) . . . . ?
N3 Cu1 N2 C6 79.3(6) . . . . ?
N1 Cu1 N2 C6 10.1(2) . . . . ?
O1 Cu1 N3 N4 -23.3(3) . . . . ?
N2 Cu1 N3 N4 83.6(7) . . . . ?
N1 Cu1 N3 N4 151.7(3) . . . . ?
C5 N1 C1 C2 0.1(5) . . . . ?
Cu1 N1 C1 C2 177.3(3) . . . . ?
N1 C1 C2 C3 0.8(6) . . . . ?
C1 C2 C3 C4 -0.9(6) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C1 N1 C5 C4 -0.9(5) . . . . ?
Cu1 N1 C5 C4 -178.4(3) . . . . ?
C1 N1 C5 C6 178.6(3) . . . . ?
Cu1 N1 C5 C6 1.1(4) . . . . ?
C3 C4 C5 N1 0.8(5) . . . . ?
C3 C4 C5 C6 -178.7(3) . . . . ?
C6 N2 C8 C9 178.8(3) . . . . ?
Cu1 N2 C8 C9 -5.3(5) . . . . ?
N2 C8 C9 C10 177.6(3) . . . . ?
N2 C8 C9 C14 -1.7(5) . . . . ?
C14 C9 C10 C11 1.5(5) . . . . ?
C8 C9 C10 C11 -177.8(3) . . . . ?
C9 C10 C11 C12 -2.0(6) . . . . ?
C10 C11 C12 C13 0.6(6) . . . . ?
C11 C12 C13 C14 1.3(6) . . . . ?
Cu1 O1 C14 C13 -170.5(2) . . . . ?
Cu1 O1 C14 C9 9.4(5) . . . . ?
C12 C13 C14 O1 178.1(3) . . . . ?
C12 C13 C14 C9 -1.8(5) . . . . ?
C10 C9 C14 O1 -179.5(3) . . . . ?
C8 C9 C14 O1 -0.2(5) . . . . ?
C10 C9 C14 C13 0.4(5) . . . . ?
C8 C9 C14 C13 179.7(3) . . . . ?
C8 N2 C6 C5 164.5(3) . . . . ?
Cu1 N2 C6 C5 -11.7(3) . . . . ?
C8 N2 C6 C7 -73.8(4) . . . . ?
Cu1 N2 C6 C7 110.0(3) . . . . ?
N1 C5 C6 N2 6.6(4) . . . . ?
C4 C5 C6 N2 -173.9(3) . . . . ?
N1 C5 C6 C7 -114.3(3) . . . . ?
C4 C5 C6 C7 65.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.00
_diffrn_reflns_theta_full        25.51
_diffrn_measured_fraction_theta_full 1.00
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.120
_database_code_depnum_ccdc_archive 'CCDC 974878'
#######################################################################
#
#                 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_Complex_4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H26 Cu2 N6 O2 S2'
_chemical_formula_sum            'C30 H26 Cu2 N6 O2 S2'
_chemical_formula_weight         693.81

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'
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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5390(4)
_cell_length_b                   18.0643(9)
_cell_length_c                   11.6901(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.230(3)
_cell_angle_gamma                90.00
_cell_volume                     1503.21(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3466
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      23.19

_exptl_crystal_description       Rod
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             708
_exptl_absorpt_coefficient_mu    1.592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.494
_exptl_absorpt_correction_T_max  0.641
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28973
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_sigmaI/netI    0.0890
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         35.64
_reflns_number_total             6949
_reflns_number_gt                5638
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 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)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6949
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1618
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0755
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.001
_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 0.71025(3) 0.010371(13) 0.00587(2) 0.04507(9) Uani 1 1 d . . .
S1 S 0.63270(11) -0.17966(4) -0.28266(6) 0.0774(2) Uani 1 1 d . . .
O1 O 0.60547(19) -0.05111(7) 0.10208(12) 0.0481(3) Uani 1 1 d . . .
N1 N 0.8274(2) 0.08165(10) -0.08023(16) 0.0519(4) Uani 1 1 d . . .
N2 N 0.7792(2) 0.08685(9) 0.12910(15) 0.0474(4) Uani 1 1 d . . .
N3 N 0.7006(3) -0.07044(10) -0.10585(17) 0.0571(5) Uani 1 1 d . . .
C1 C 0.8610(3) 0.06909(14) -0.1856(2) 0.0645(6) Uani 1 1 d . . .
H1 H 0.8209 0.0247 -0.2262 0.077 Uiso 1 1 calc R . .
C2 C 0.9508(4) 0.11890(18) -0.2342(3) 0.0791(8) Uani 1 1 d . . .
H2 H 0.9708 0.1089 -0.3071 0.095 Uiso 1 1 calc R . .
C3 C 1.0118(4) 0.18429(17) -0.1740(3) 0.0859(9) Uani 1 1 d . . .
H3 H 1.0766 0.2185 -0.2047 0.103 Uiso 1 1 calc R . .
C4 C 0.9764(3) 0.19902(14) -0.0675(3) 0.0754(8) Uani 1 1 d . . .
H4 H 1.0149 0.2433 -0.0263 0.091 Uiso 1 1 calc R . .
C5 C 0.8818(3) 0.14592(12) -0.0236(2) 0.0554(6) Uani 1 1 d . . .
C6 C 0.8301(3) 0.15872(11) 0.0889(2) 0.0557(6) Uani 1 1 d . . .
H6 H 0.9388 0.1791 0.1527 0.067 Uiso 1 1 calc R . .
C7 C 0.6651(4) 0.21263(12) 0.0640(2) 0.0726(7) Uani 1 1 d . . .
H7A H 0.5560 0.1914 0.0054 0.109 Uiso 1 1 calc R . .
H7B H 0.6963 0.2583 0.0331 0.109 Uiso 1 1 calc R . .
H7C H 0.6393 0.2220 0.1378 0.109 Uiso 1 1 calc R . .
C8 C 0.7831(3) 0.07941(11) 0.2395(2) 0.0535(5) Uani 1 1 d . . .
H8 H 0.8243 0.1199 0.2905 0.064 Uiso 1 1 calc R . .
C9 C 0.7303(3) 0.01491(12) 0.29091(19) 0.0514(5) Uani 1 1 d . . .
C10 C 0.7585(4) 0.01420(15) 0.4167(2) 0.0746(7) Uani 1 1 d . . .
H10 H 0.8085 0.0560 0.4624 0.089 Uiso 1 1 calc R . .
C11 C 0.7153(4) -0.04538(18) 0.4730(2) 0.0861(9) Uani 1 1 d . . .
H11 H 0.7368 -0.0445 0.5560 0.103 Uiso 1 1 calc R . .
C12 C 0.6386(3) -0.10767(15) 0.4051(2) 0.0741(7) Uani 1 1 d . . .
H12 H 0.6100 -0.1491 0.4430 0.089 Uiso 1 1 calc R . .
C13 C 0.6046(3) -0.10847(12) 0.2824(2) 0.0589(6) Uani 1 1 d . . .
H13 H 0.5517 -0.1505 0.2384 0.071 Uiso 1 1 calc R . .
C14 C 0.6471(3) -0.04796(11) 0.22129(19) 0.0469(5) Uani 1 1 d . . .
C15 C 0.6725(3) -0.11586(12) -0.1791(2) 0.0516(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9255(13) . ?
Cu1 N2 1.9393(16) . ?
Cu1 N3 1.9440(18) . ?
Cu1 N1 2.0093(17) . ?
Cu1 O1 2.4127(14) 3_655 ?
S1 C15 1.626(2) . ?
O1 C14 1.325(2) . ?
O1 Cu1 2.4127(14) 3_655 ?
N1 C5 1.332(3) . ?
N1 C1 1.356(3) . ?
N2 C8 1.288(2) . ?
N2 C6 1.474(2) . ?
N3 C15 1.154(2) . ?
C1 C2 1.358(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.508(3) . ?
C6 C7 1.530(3) . ?
C6 H6 0.9800 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.427(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.415(3) . ?
C9 C14 1.418(3) . ?
C10 C11 1.356(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.399(3) . ?
C13 H13 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
O1 Cu1 N2 92.19(6) . . ?
O1 Cu1 N3 91.57(7) . . ?
N2 Cu1 N3 167.30(7) . . ?
O1 Cu1 N1 174.19(6) . . ?
N2 Cu1 N1 82.01(7) . . ?
N3 Cu1 N1 94.02(8) . . ?
O1 Cu1 O1 87.57(5) . 3_655 ?
N2 Cu1 O1 98.52(6) . 3_655 ?
N3 Cu1 O1 93.75(6) . 3_655 ?
N1 Cu1 O1 93.63(6) . 3_655 ?
C14 O1 Cu1 126.08(12) . . ?
C14 O1 Cu1 112.84(11) . 3_655 ?
Cu1 O1 Cu1 92.43(5) . 3_655 ?
C5 N1 C1 118.6(2) . . ?
C5 N1 Cu1 115.06(15) . . ?
C1 N1 Cu1 126.31(16) . . ?
C8 N2 C6 119.26(17) . . ?
C8 N2 Cu1 125.59(14) . . ?
C6 N2 Cu1 115.15(13) . . ?
C15 N3 Cu1 171.68(18) . . ?
N1 C1 C2 122.5(3) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 119.0(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 118.3(3) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 121.9(2) . . ?
N1 C5 C6 116.20(19) . . ?
C4 C5 C6 121.9(2) . . ?
N2 C6 C5 108.19(17) . . ?
N2 C6 C7 109.93(18) . . ?
C5 C6 C7 111.03(18) . . ?
N2 C6 H6 109.2 . . ?
C5 C6 H6 109.2 . . ?
C7 C6 H6 109.2 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C9 126.16(19) . . ?
N2 C8 H8 116.9 . . ?
C9 C8 H8 116.9 . . ?
C10 C9 C14 118.4(2) . . ?
C10 C9 C8 118.6(2) . . ?
C14 C9 C8 122.98(19) . . ?
C11 C10 C9 122.3(2) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C10 C11 C12 119.1(3) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 122.0(2) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
O1 C14 C13 119.23(19) . . ?
O1 C14 C9 123.03(18) . . ?
C13 C14 C9 117.7(2) . . ?
N3 C15 S1 179.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Cu1 O1 C14 -22.34(15) . . . . ?
N3 Cu1 O1 C14 145.53(15) . . . . ?
O1 Cu1 O1 C14 -120.78(16) 3_655 . . . ?
N2 Cu1 O1 Cu1 98.44(6) . . . 3_655 ?
N3 Cu1 O1 Cu1 -93.69(6) . . . 3_655 ?
O1 Cu1 O1 Cu1 0.0 3_655 . . 3_655 ?
N2 Cu1 N1 C5 -4.54(14) . . . . ?
N3 Cu1 N1 C5 -172.41(15) . . . . ?
O1 Cu1 N1 C5 93.56(14) 3_655 . . . ?
N2 Cu1 N1 C1 172.94(18) . . . . ?
N3 Cu1 N1 C1 5.07(18) . . . . ?
O1 Cu1 N1 C1 -88.95(17) 3_655 . . . ?
O1 Cu1 N2 C8 13.80(17) . . . . ?
N3 Cu1 N2 C8 -93.3(4) . . . . ?
N1 Cu1 N2 C8 -165.83(18) . . . . ?
O1 Cu1 N2 C8 101.67(17) 3_655 . . . ?
O1 Cu1 N2 C6 -166.08(14) . . . . ?
N3 Cu1 N2 C6 86.8(4) . . . . ?
N1 Cu1 N2 C6 14.29(14) . . . . ?
O1 Cu1 N2 C6 -78.21(14) 3_655 . . . ?
C5 N1 C1 C2 1.3(3) . . . . ?
Cu1 N1 C1 C2 -176.11(17) . . . . ?
N1 C1 C2 C3 0.6(4) . . . . ?
C1 C2 C3 C4 -1.7(4) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C1 N1 C5 C4 -2.0(3) . . . . ?
Cu1 N1 C5 C4 175.66(16) . . . . ?
C1 N1 C5 C6 176.31(18) . . . . ?
Cu1 N1 C5 C6 -6.0(2) . . . . ?
C3 C4 C5 N1 0.9(3) . . . . ?
C3 C4 C5 C6 -177.4(2) . . . . ?
C8 N2 C6 C5 159.89(18) . . . . ?
Cu1 N2 C6 C5 -20.2(2) . . . . ?
C8 N2 C6 C7 -78.7(2) . . . . ?
Cu1 N2 C6 C7 101.16(18) . . . . ?
N1 C5 C6 N2 16.6(2) . . . . ?
C4 C5 C6 N2 -165.03(19) . . . . ?
N1 C5 C6 C7 -104.1(2) . . . . ?
C4 C5 C6 C7 74.3(3) . . . . ?
C6 N2 C8 C9 177.1(2) . . . . ?
Cu1 N2 C8 C9 -2.8(3) . . . . ?
N2 C8 C9 C10 174.7(2) . . . . ?
N2 C8 C9 C14 -6.7(3) . . . . ?
C14 C9 C10 C11 2.5(4) . . . . ?
C8 C9 C10 C11 -178.8(2) . . . . ?
C9 C10 C11 C12 -0.8(4) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
Cu1 O1 C14 C13 -161.29(14) . . . . ?
Cu1 O1 C14 C13 87.37(19) 3_655 . . . ?
Cu1 O1 C14 C9 20.0(3) . . . . ?
Cu1 O1 C14 C9 -91.3(2) 3_655 . . . ?
C12 C13 C14 O1 -177.8(2) . . . . ?
C12 C13 C14 C9 0.9(3) . . . . ?
C10 C9 C14 O1 176.2(2) . . . . ?
C8 C9 C14 O1 -2.4(3) . . . . ?
C10 C9 C14 C13 -2.5(3) . . . . ?
C8 C9 C14 C13 178.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.00
_diffrn_reflns_theta_full        35.64
_diffrn_measured_fraction_theta_full 1.00
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.057
_database_code_depnum_ccdc_archive 'CCDC 974879'
#######################################################################
#
#                 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_Complex_5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 Cu N3 O2'
_chemical_formula_sum            'C15 H13 Cu N3 O2'
_chemical_formula_weight         330.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.9869(4)
_cell_length_b                   16.1585(7)
_cell_length_c                   10.9541(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.580(2)
_cell_angle_gamma                90.00
_cell_volume                     1393.98(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8179
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      31.34

_exptl_crystal_description       Flakes
_exptl_crystal_colour            Blue
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             676
_exptl_absorpt_coefficient_mu    1.574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.573
_exptl_absorpt_correction_T_max  0.675
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20121
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         32.36
_reflns_number_total             4774
_reflns_number_gt                3751
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0459P)²+0.2477P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4774
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0900
_refine_ls_wR_factor_gt          0.0833
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.34538(2) 0.006247(10) 0.377083(16) 0.03912(7) Uani 1 1 d . . .
C9 C 0.15427(18) 0.03956(10) 0.61626(13) 0.0410(3) Uani 1 1 d . . .
C6 C 0.2479(2) 0.18033(9) 0.36530(13) 0.0433(3) Uani 1 1 d . . .
H6 H 0.1356 0.2065 0.3532 0.052 Uiso 1 1 calc R . .
C15 C 0.5054(2) -0.14375(8) 0.27497(13) 0.0407(3) Uani 1 1 d . . .
C5 C 0.29374(18) 0.15819(9) 0.24157(13) 0.0393(3) Uani 1 1 d . . .
C8 C 0.16375(18) 0.10562(9) 0.53075(13) 0.0409(3) Uani 1 1 d . . .
H8 H 0.1064 0.1542 0.5431 0.049 Uiso 1 1 calc R . .
C14 C 0.24164(19) -0.03690(10) 0.61050(14) 0.0436(3) Uani 1 1 d . . .
C4 C 0.2861(2) 0.21586(10) 0.14687(16) 0.0504(4) Uani 1 1 d . . .
H4 H 0.2551 0.2703 0.1592 0.060 Uiso 1 1 calc R . .
C13 C 0.2241(2) -0.09608(11) 0.70229(17) 0.0549(4) Uani 1 1 d . . .
H13 H 0.2764 -0.1474 0.7001 0.066 Uiso 1 1 calc R . .
C3 C 0.3249(3) 0.19135(13) 0.03452(17) 0.0600(5) Uani 1 1 d . . .
H3 H 0.3231 0.2293 -0.0295 0.072 Uiso 1 1 calc R . .
C10 C 0.0607(2) 0.05336(12) 0.71240(15) 0.0519(4) Uani 1 1 d . . .
H10 H 0.0046 0.1036 0.7157 0.062 Uiso 1 1 calc R . .
C7 C 0.3798(4) 0.23978(13) 0.43403(18) 0.0797(7) Uani 1 1 d . . .
H7A H 0.3478 0.2549 0.5117 0.120 Uiso 1 1 calc R . .
H7B H 0.3857 0.2885 0.3848 0.120 Uiso 1 1 calc R . .
H7C H 0.4888 0.2132 0.4487 0.120 Uiso 1 1 calc R . .
C2 C 0.3666(3) 0.10965(14) 0.01833(17) 0.0674(5) Uani 1 1 d . . .
H2 H 0.3886 0.0912 -0.0578 0.081 Uiso 1 1 calc R . .
C11 C 0.0499(3) -0.00506(13) 0.80104(18) 0.0613(5) Uani 1 1 d . . .
H11 H -0.0115 0.0054 0.8645 0.074 Uiso 1 1 calc R . .
C1 C 0.3749(3) 0.05638(12) 0.11600(16) 0.0591(5) Uani 1 1 d . . .
H1 H 0.4057 0.0017 0.1053 0.071 Uiso 1 1 calc R . .
C12 C 0.1319(2) -0.07998(14) 0.79474(17) 0.0611(5) Uani 1 1 d . . .
H12 H 0.1243 -0.1202 0.8543 0.073 Uiso 1 1 calc R . .
N2 N 0.24429(16) 0.10400(7) 0.43831(10) 0.0377(2) Uani 1 1 d . . .
N1 N 0.34041(16) 0.07982(8) 0.22723(11) 0.0414(3) Uani 1 1 d . . .
N3 N 0.4160(2) -0.09067(8) 0.29488(14) 0.0535(3) Uani 1 1 d . . .
O1 O 0.33692(16) -0.05436(7) 0.52741(11) 0.0520(3) Uani 1 1 d . . .
O2 O 0.59335(18) -0.19982(7) 0.25224(12) 0.0585(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 O1 1.9267(11) . ?
Cu1 N3 1.9366(14) . ?
Cu1 N2 1.9434(12) . ?
Cu1 N1 2.0218(12) . ?
C9 C10 1.407(2) . ?
C9 C14 1.425(2) . ?
C9 C8 1.430(2) . ?
C6 N2 1.4729(18) . ?
C6 C5 1.505(2) . ?
C6 C7 1.528(3) . ?
C15 N3 1.160(2) . ?
C15 O2 1.1979(18) . ?
C5 N1 1.3367(18) . ?
C5 C4 1.388(2) . ?
C8 N2 1.2870(18) . ?
C14 O1 1.3107(19) . ?
C14 C13 1.411(2) . ?
C4 C3 1.377(2) . ?
C13 C12 1.373(3) . ?
C3 C2 1.380(3) . ?
C10 C11 1.367(3) . ?
C2 C1 1.366(3) . ?
C11 C12 1.383(3) . ?
C1 N1 1.348(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
O1 Cu1 N3 92.33(6) . . ?
O1 Cu1 N2 92.44(5) . . ?
N3 Cu1 N2 170.95(6) . . ?
O1 Cu1 N1 173.73(5) . . ?
N3 Cu1 N1 93.78(6) . . ?
N2 Cu1 N1 81.32(5) . . ?
C10 C9 C14 119.70(14) . . ?
C10 C9 C8 117.68(15) . . ?
C14 C9 C8 122.55(13) . . ?
N2 C6 C5 108.64(11) . . ?
N2 C6 C7 109.44(13) . . ?
C5 C6 C7 109.99(15) . . ?
N3 C15 O2 177.92(18) . . ?
N1 C5 C4 121.78(14) . . ?
N1 C5 C6 116.46(12) . . ?
C4 C5 C6 121.76(13) . . ?
N2 C8 C9 126.01(14) . . ?
O1 C14 C13 119.12(15) . . ?
O1 C14 C9 124.23(13) . . ?
C13 C14 C9 116.64(15) . . ?
C3 C4 C5 119.11(16) . . ?
C12 C13 C14 121.74(18) . . ?
C4 C3 C2 119.02(16) . . ?
C11 C10 C9 121.75(18) . . ?
C1 C2 C3 118.91(17) . . ?
C10 C11 C12 118.85(18) . . ?
N1 C1 C2 122.71(17) . . ?
C13 C12 C11 121.28(17) . . ?
C8 N2 C6 117.87(12) . . ?
C8 N2 Cu1 125.37(10) . . ?
C6 N2 Cu1 116.52(9) . . ?
C5 N1 C1 118.39(13) . . ?
C5 N1 Cu1 115.46(10) . . ?
C1 N1 Cu1 126.12(11) . . ?
C15 N3 Cu1 157.15(14) . . ?
C14 O1 Cu1 126.23(10) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        32.36
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 974880'
