# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1045737'
_audit_update_record             
;
2015-03-02 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 Cl2 Cu N3 O'
_chemical_formula_weight         389.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   9.268(4)
_cell_length_b                   13.526(6)
_cell_length_c                   13.154(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.941(6)
_cell_angle_gamma                90.00
_cell_volume                     1633.1(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5687
_cell_measurement_theta_min      2.6817
_cell_measurement_theta_max      27.7718

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             796
_exptl_absorpt_coefficient_mu    1.668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6805
_exptl_absorpt_correction_T_max  0.7762
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12307
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3206
_reflns_number_gt                2679
_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)+(0.0739P)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         3206
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1176
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.51038(4) 0.12907(3) 0.64797(3) 0.01501(15) Uani 1 1 d . . .
Cl1 Cl 0.68748(8) 0.01896(6) 0.62828(5) 0.0204(2) Uani 1 1 d . . .
Cl2 Cl 0.52943(9) 0.16610(6) 0.83487(5) 0.0205(2) Uani 1 1 d . . .
N1 N 0.6207(3) 0.2518(2) 0.62093(18) 0.0168(6) Uani 1 1 d . . .
N3 N 0.3454(3) 0.03126(19) 0.64367(18) 0.0156(5) Uani 1 1 d . . .
N2 N 0.3389(3) 0.22181(19) 0.60551(17) 0.0150(6) Uani 1 1 d . . .
C7 C 0.2192(3) 0.1838(2) 0.6574(2) 0.0196(7) Uani 1 1 d . . .
H7A H 0.1272 0.2117 0.6262 0.024 Uiso 1 1 calc R . .
H7B H 0.2347 0.2023 0.7294 0.024 Uiso 1 1 calc R . .
C1 C 0.3873(3) 0.3219(2) 0.6389(2) 0.0183(7) Uani 1 1 d . . .
H1C H 0.3800 0.3303 0.7112 0.022 Uiso 1 1 calc R . .
H1D H 0.3259 0.3710 0.6005 0.022 Uiso 1 1 calc R . .
C3 C 0.6015(4) 0.4272(3) 0.6088(2) 0.0211(7) Uani 1 1 d . . .
H3 H 0.5448 0.4839 0.6092 0.025 Uiso 1 1 calc R . .
C8 C 0.2158(3) 0.0733(2) 0.6471(2) 0.0187(7) Uani 1 1 d . . .
C12 C 0.3525(4) -0.0674(2) 0.6358(2) 0.0199(7) Uani 1 1 d . . .
H12 H 0.4423 -0.0971 0.6326 0.024 Uiso 1 1 calc R . .
C2 C 0.5419(3) 0.3350(2) 0.6207(2) 0.0185(7) Uani 1 1 d . . .
C4 C 0.7462(4) 0.4336(3) 0.5963(2) 0.0259(8) Uani 1 1 d . . .
H4 H 0.7885 0.4948 0.5873 0.031 Uiso 1 1 calc R . .
C5 C 0.8271(4) 0.3485(3) 0.5973(2) 0.0255(8) Uani 1 1 d . . .
H5 H 0.9255 0.3515 0.5902 0.031 Uiso 1 1 calc R . .
C10 C 0.0984(4) -0.0826(3) 0.6356(2) 0.0271(8) Uani 1 1 d . . .
H10 H 0.0148 -0.1210 0.6331 0.033 Uiso 1 1 calc R . .
C11 C 0.2306(4) -0.1258(3) 0.6323(2) 0.0232(7) Uani 1 1 d . . .
H11 H 0.2382 -0.1941 0.6277 0.028 Uiso 1 1 calc R . .
C9 C 0.0905(4) 0.0192(3) 0.6427(2) 0.0234(7) Uani 1 1 d . . .
H9 H 0.0015 0.0503 0.6445 0.028 Uiso 1 1 calc R . .
C6 C 0.7615(4) 0.2591(3) 0.6087(2) 0.0224(7) Uani 1 1 d . . .
H6 H 0.8165 0.2017 0.6079 0.027 Uiso 1 1 calc R . .
C13 C 0.3036(3) 0.2170(2) 0.4915(2) 0.0166(6) Uani 1 1 d . . .
H13A H 0.3875 0.2391 0.4611 0.020 Uiso 1 1 calc R . .
H13B H 0.2849 0.1487 0.4713 0.020 Uiso 1 1 calc R . .
C14 C 0.1779(4) 0.2767(2) 0.4509(2) 0.0194(7) Uani 1 1 d . . .
C15 C 0.0774(4) 0.3249(3) 0.4177(2) 0.0236(8) Uani 1 1 d . . .
H15 H -0.0024 0.3632 0.3913 0.028 Uiso 1 1 calc R . .
O1 O 0.8175(3) 0.4667(2) 0.36423(18) 0.0317(6) Uani 1 1 d . . .
H1B H 0.7525 0.4240 0.3716 0.048 Uiso 1 1 d R . .
H1A H 0.7936 0.4812 0.3013 0.048 Uiso 1 1 d 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 N1 2.007(3) . ?
Cu1 N3 2.017(3) . ?
Cu1 N2 2.041(3) . ?
Cu1 Cl1 2.2576(11) . ?
Cu1 Cl2 2.4912(13) . ?
N1 C6 1.340(4) . ?
N1 C2 1.342(4) . ?
N3 C8 1.336(4) . ?
N3 C12 1.340(4) . ?
N2 C1 1.473(4) . ?
N2 C7 1.474(4) . ?
N2 C13 1.492(4) . ?
C7 C8 1.501(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C1 C2 1.495(5) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C3 C4 1.376(5) . ?
C3 C2 1.381(5) . ?
C3 H3 0.9300 . ?
C8 C9 1.367(5) . ?
C12 C11 1.374(5) . ?
C12 H12 0.9300 . ?
C4 C5 1.373(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(5) . ?
C5 H5 0.9300 . ?
C10 C11 1.364(5) . ?
C10 C9 1.382(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C9 H9 0.9300 . ?
C6 H6 0.9300 . ?
C13 C14 1.457(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.171(5) . ?
C15 H15 0.9300 . ?
O1 H1B 0.8500 . ?
O1 H1A 0.8501 . ?

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 Cu1 N3 160.14(11) . . ?
N1 Cu1 N2 80.78(11) . . ?
N3 Cu1 N2 80.62(11) . . ?
N1 Cu1 Cl1 97.41(9) . . ?
N3 Cu1 Cl1 97.14(9) . . ?
N2 Cu1 Cl1 157.67(7) . . ?
N1 Cu1 Cl2 92.30(7) . . ?
N3 Cu1 Cl2 96.29(7) . . ?
N2 Cu1 Cl2 95.33(7) . . ?
Cl1 Cu1 Cl2 107.00(3) . . ?
C6 N1 C2 118.5(3) . . ?
C6 N1 Cu1 127.6(2) . . ?
C2 N1 Cu1 113.8(2) . . ?
C8 N3 C12 118.7(3) . . ?
C8 N3 Cu1 113.7(2) . . ?
C12 N3 Cu1 127.6(2) . . ?
C1 N2 C7 113.6(2) . . ?
C1 N2 C13 110.8(2) . . ?
C7 N2 C13 112.1(2) . . ?
C1 N2 Cu1 106.84(19) . . ?
C7 N2 Cu1 105.46(19) . . ?
C13 N2 Cu1 107.61(18) . . ?
N2 C7 C8 108.3(3) . . ?
N2 C7 H7A 110.0 . . ?
C8 C7 H7A 110.0 . . ?
N2 C7 H7B 110.0 . . ?
C8 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
N2 C1 C2 108.7(3) . . ?
N2 C1 H1C 110.0 . . ?
C2 C1 H1C 110.0 . . ?
N2 C1 H1D 110.0 . . ?
C2 C1 H1D 110.0 . . ?
H1C C1 H1D 108.3 . . ?
C4 C3 C2 118.8(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
N3 C8 C9 122.2(3) . . ?
N3 C8 C7 114.8(3) . . ?
C9 C8 C7 123.0(3) . . ?
N3 C12 C11 121.7(3) . . ?
N3 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
N1 C2 C3 122.1(3) . . ?
N1 C2 C1 115.7(3) . . ?
C3 C2 C1 122.2(3) . . ?
C5 C4 C3 119.1(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C11 C10 C9 119.0(3) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 119.4(3) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C8 C9 C10 118.9(3) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
N1 C6 C5 122.1(3) . . ?
N1 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C14 C13 N2 113.4(2) . . ?
C14 C13 H13A 108.9 . . ?
N2 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
N2 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 179.5(4) . . ?
C14 C15 H15 180.0 . . ?
H1B O1 H1A 100.0 . . ?

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
N3 Cu1 N1 C6 -143.9(3) . . . . ?
N2 Cu1 N1 C6 -164.6(3) . . . . ?
Cl1 Cu1 N1 C6 -7.1(3) . . . . ?
Cl2 Cu1 N1 C6 100.3(2) . . . . ?
N3 Cu1 N1 C2 39.5(4) . . . . ?
N2 Cu1 N1 C2 18.8(2) . . . . ?
Cl1 Cu1 N1 C2 176.34(19) . . . . ?
Cl2 Cu1 N1 C2 -76.2(2) . . . . ?
N1 Cu1 N3 C8 -39.2(4) . . . . ?
N2 Cu1 N3 C8 -18.49(19) . . . . ?
Cl1 Cu1 N3 C8 -176.03(19) . . . . ?
Cl2 Cu1 N3 C8 75.90(19) . . . . ?
N1 Cu1 N3 C12 139.3(3) . . . . ?
N2 Cu1 N3 C12 160.0(3) . . . . ?
Cl1 Cu1 N3 C12 2.5(2) . . . . ?
Cl2 Cu1 N3 C12 -105.6(2) . . . . ?
N1 Cu1 N2 C1 -31.91(18) . . . . ?
N3 Cu1 N2 C1 155.08(19) . . . . ?
Cl1 Cu1 N2 C1 -119.0(2) . . . . ?
Cl2 Cu1 N2 C1 59.56(18) . . . . ?
N1 Cu1 N2 C7 -153.1(2) . . . . ?
N3 Cu1 N2 C7 33.93(18) . . . . ?
Cl1 Cu1 N2 C7 119.9(2) . . . . ?
Cl2 Cu1 N2 C7 -61.58(18) . . . . ?
N1 Cu1 N2 C13 87.1(2) . . . . ?
N3 Cu1 N2 C13 -85.9(2) . . . . ?
Cl1 Cu1 N2 C13 0.1(3) . . . . ?
Cl2 Cu1 N2 C13 178.62(18) . . . . ?
C1 N2 C7 C8 -160.0(2) . . . . ?
C13 N2 C7 C8 73.4(3) . . . . ?
Cu1 N2 C7 C8 -43.4(3) . . . . ?
C7 N2 C1 C2 155.0(2) . . . . ?
C13 N2 C1 C2 -77.8(3) . . . . ?
Cu1 N2 C1 C2 39.2(3) . . . . ?
C12 N3 C8 C9 -0.1(4) . . . . ?
Cu1 N3 C8 C9 178.5(2) . . . . ?
C12 N3 C8 C7 179.2(3) . . . . ?
Cu1 N3 C8 C7 -2.2(3) . . . . ?
N2 C7 C8 N3 31.2(3) . . . . ?
N2 C7 C8 C9 -149.5(3) . . . . ?
C8 N3 C12 C11 -0.7(4) . . . . ?
Cu1 N3 C12 C11 -179.1(2) . . . . ?
C6 N1 C2 C3 -0.3(4) . . . . ?
Cu1 N1 C2 C3 176.5(2) . . . . ?
C6 N1 C2 C1 -177.7(3) . . . . ?
Cu1 N1 C2 C1 -0.8(3) . . . . ?
C4 C3 C2 N1 0.3(4) . . . . ?
C4 C3 C2 C1 177.5(3) . . . . ?
N2 C1 C2 N1 -26.3(3) . . . . ?
N2 C1 C2 C3 156.4(3) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 1.2(5) . . . . ?
C9 C10 C11 C12 -0.2(5) . . . . ?
N3 C12 C11 C10 0.8(5) . . . . ?
N3 C8 C9 C10 0.8(5) . . . . ?
C7 C8 C9 C10 -178.5(3) . . . . ?
C11 C10 C9 C8 -0.6(5) . . . . ?
C2 N1 C6 C5 0.8(4) . . . . ?
Cu1 N1 C6 C5 -175.6(2) . . . . ?
C4 C5 C6 N1 -1.3(5) . . . . ?
C1 N2 C13 C14 -66.2(3) . . . . ?
C7 N2 C13 C14 61.8(3) . . . . ?
Cu1 N2 C13 C14 177.3(2) . . . . ?
N2 C13 C14 C15 138(50) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.986
_refine_diff_density_min         -1.500
_refine_diff_density_rms         0.159
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1045738'
_audit_update_record             
;
2015-03-02 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H38 Cu2 N8 O2, 2(Cl O4)'
_chemical_formula_sum            'C36 H38 Cl2 Cu2 N8 O10'
_chemical_formula_weight         940.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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                   12.006(5)
_cell_length_b                   9.927(4)
_cell_length_c                   17.447(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.68(2)
_cell_angle_gamma                90.00
_cell_volume                     1858.0(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4091
_cell_measurement_theta_min      2.432
_cell_measurement_theta_max      26.778

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             964
_exptl_absorpt_coefficient_mu    1.360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_T_max  0.794
_exptl_absorpt_process_details   'Bruker SHELXTL'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            12925
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3265
_reflns_number_gt                2837
_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)+(0.0636P)²+27.2568P] 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         3265
_refine_ls_number_parameters     251
_refine_ls_number_restraints     49
_refine_ls_R_factor_all          0.1174
_refine_ls_R_factor_gt           0.1071
_refine_ls_wR_factor_ref         0.2563
_refine_ls_wR_factor_gt          0.2503
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_restrained_S_all      1.206
_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 0.39030(10) 0.46615(12) 1.02176(7) 0.0285(4) Uani 1 1 d . . .
N1 N 0.2036(7) 0.5118(9) 0.9563(5) 0.038(2) Uani 1 1 d . . .
N3 N 0.3325(10) 0.2838(9) 0.9811(6) 0.045(2) Uani 1 1 d . . .
N4 N 0.1967(14) 0.125(2) 0.9264(9) 0.109(6) Uani 1 1 d D . .
Cl1 Cl 0.1660(2) 0.2605(3) 0.66289(18) 0.0438(7) Uani 1 1 d . . .
O1 O 0.4315(6) 0.5569(7) 0.9215(4) 0.0389(17) Uani 1 1 d . . .
O2 O 0.0787(10) 0.3383(12) 0.5932(9) 0.113(5) Uani 1 1 d . . .
O3 O 0.1745(14) 0.284(2) 0.7402(9) 0.161(8) Uani 1 1 d . . .
O4 O 0.2765(8) 0.2544(13) 0.6571(6) 0.081(3) Uani 1 1 d . . .
O5 O 0.1100(11) 0.1288(11) 0.6414(8) 0.094(4) Uani 1 1 d . . .
N2 N 0.3938(6) 0.6329(5) 1.0843(4) 0.038(2) Uani 1 1 d GU . .
C1 C 0.4959(5) 0.7013(7) 1.1457(4) 0.041(2) Uani 1 1 d GU . .
H1 H 0.5747 0.6625 1.1680 0.049 Uiso 1 1 calc R . .
C2 C 0.4801(8) 0.8278(7) 1.1737(5) 0.063(4) Uani 1 1 d GU . .
H2 H 0.5484 0.8736 1.2147 0.076 Uiso 1 1 calc R . .
C3 C 0.3623(10) 0.8858(6) 1.1403(6) 0.112(6) Uani 1 1 d GU . .
H3 H 0.3518 0.9704 1.1590 0.135 Uiso 1 1 calc R . .
C4 C 0.2602(7) 0.8173(8) 1.0789(6) 0.103(6) Uani 1 1 d GU . .
H4 H 0.1814 0.8562 1.0565 0.124 Uiso 1 1 calc R . .
C5 C 0.2759(5) 0.6909(8) 1.0509(5) 0.053(3) Uani 1 1 d GU . .
C6 C 0.1741(10) 0.6263(17) 0.9961(8) 0.066(4) Uani 1 1 d . . .
H6A H 0.1211 0.6884 0.9518 0.079 Uiso 1 1 calc R . .
H6B H 0.1280 0.5950 1.0263 0.079 Uiso 1 1 calc R . .
C7 C 0.1392(10) 0.3881(16) 0.9600(8) 0.068(5) Uani 1 1 d . . .
H7A H 0.0558 0.3860 0.9129 0.081 Uiso 1 1 calc R . .
H7B H 0.1327 0.3846 1.0134 0.081 Uiso 1 1 calc R . .
C8 C 0.2117(17) 0.2732(14) 0.9543(7) 0.067(4) Uani 1 1 d . . .
C10 C 0.3004(10) 0.0633(11) 0.9380(7) 0.043(3) Uani 1 1 d . . .
H10 H 0.3131 -0.0251 0.9262 0.052 Uiso 1 1 calc R . .
C11 C 0.3831(13) 0.1654(12) 0.9720(7) 0.053(3) Uani 1 1 d . . .
H11 H 0.4677 0.1556 0.9880 0.063 Uiso 1 1 calc R . .
C12 C 0.1709(9) 0.5396(11) 0.8648(6) 0.036(2) Uani 1 1 d . . .
H12A H 0.1890 0.4591 0.8408 0.043 Uiso 1 1 calc R . .
H12B H 0.0816 0.5543 0.8344 0.043 Uiso 1 1 calc R . .
C13 C 0.2335(8) 0.6551(9) 0.8460(6) 0.028(2) Uani 1 1 d . . .
C14 C 0.1597(9) 0.7575(10) 0.7908(6) 0.035(2) Uani 1 1 d . . .
H14 H 0.0749 0.7590 0.7754 0.042 Uiso 1 1 calc R . .
C15 C 0.2074(10) 0.8535(10) 0.7594(7) 0.040(3) Uani 1 1 d . . .
H15 H 0.1566 0.9207 0.7235 0.048 Uiso 1 1 calc R . .
C16 C 0.3344(11) 0.8502(11) 0.7818(7) 0.047(3) Uani 1 1 d . . .
H16 H 0.3692 0.9148 0.7605 0.056 Uiso 1 1 calc R . .
C17 C 0.4077(9) 0.7508(12) 0.8356(6) 0.041(3) Uani 1 1 d . . .
H17 H 0.4922 0.7500 0.8497 0.049 Uiso 1 1 calc R . .
C18 C 0.3628(9) 0.6539(11) 0.8691(6) 0.035(2) Uani 1 1 d . . .
C9 C 0.071(2) 0.075(4) 0.8937(13) 0.182(16) Uani 1 1 d D . .
H9A H 0.0387 0.0586 0.8333 0.273 Uiso 1 1 calc R . .
H9B H 0.0203 0.1411 0.9034 0.273 Uiso 1 1 calc R . .
H9C H 0.0710 -0.0069 0.9226 0.273 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 1.926(7) 3_667 ?
Cu1 N3 1.954(10) . ?
Cu1 N2 1.973(5) . ?
Cu1 N1 2.058(8) . ?
Cu1 O1 2.211(7) . ?
N1 C6 1.457(16) . ?
N1 C7 1.468(16) . ?
N1 C12 1.490(12) . ?
N3 C8 1.313(19) . ?
N3 C11 1.364(16) . ?
N4 C10 1.319(18) . ?
N4 C9 1.44(3) . ?
N4 C8 1.53(2) . ?
Cl1 O3 1.327(13) . ?
Cl1 O4 1.376(10) . ?
Cl1 O2 1.425(11) . ?
Cl1 O5 1.440(11) . ?
O1 C18 1.329(11) . ?
O1 Cu1 1.926(6) 3_667 ?
N2 C1 1.3900 . ?
N2 C5 1.3900 . ?
C1 C2 1.3900 . ?
C1 H1 0.9300 . ?
C2 C3 1.3900 . ?
C2 H2 0.9300 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.330(15) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.47(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C10 C11 1.355(16) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.486(14) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.406(12) . ?
C13 C18 1.417(13) . ?
C14 C15 1.349(15) . ?
C14 H14 0.9300 . ?
C15 C16 1.393(16) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(15) . ?
C16 H16 0.9300 . ?
C17 C18 1.357(15) . ?
C17 H17 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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 N3 102.0(4) 3_667 . ?
O1 Cu1 N2 94.2(3) 3_667 . ?
N3 Cu1 N2 153.4(4) . . ?
O1 Cu1 N1 173.4(3) 3_667 . ?
N3 Cu1 N1 83.2(4) . . ?
N2 Cu1 N1 82.5(3) . . ?
O1 Cu1 O1 82.1(3) 3_667 . ?
N3 Cu1 O1 105.0(3) . . ?
N2 Cu1 O1 98.0(3) . . ?
N1 Cu1 O1 92.6(3) . . ?
C6 N1 C7 112.7(11) . . ?
C6 N1 C12 111.3(9) . . ?
C7 N1 C12 108.2(9) . . ?
C6 N1 Cu1 110.2(6) . . ?
C7 N1 Cu1 104.8(7) . . ?
C12 N1 Cu1 109.4(6) . . ?
C8 N3 C11 111.6(11) . . ?
C8 N3 Cu1 111.0(9) . . ?
C11 N3 Cu1 137.4(9) . . ?
C10 N4 C9 131(2) . . ?
C10 N4 C8 115.3(15) . . ?
C9 N4 C8 114(2) . . ?
O3 Cl1 O4 116.4(8) . . ?
O3 Cl1 O2 117.7(11) . . ?
O4 Cl1 O2 109.0(8) . . ?
O3 Cl1 O5 103.6(11) . . ?
O4 Cl1 O5 107.1(8) . . ?
O2 Cl1 O5 101.0(7) . . ?
C18 O1 Cu1 130.0(7) . 3_667 ?
C18 O1 Cu1 123.3(6) . . ?
Cu1 O1 Cu1 97.9(3) 3_667 . ?
C1 N2 C5 120.0 . . ?
C1 N2 Cu1 128.9(4) . . ?
C5 N2 Cu1 110.5(4) . . ?
C2 C1 N2 120.0 . . ?
C2 C1 H1 120.0 . . ?
N2 C1 H1 120.0 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 117.5(8) . . ?
C6 C5 N2 122.4(8) . . ?
C4 C5 N2 120.0 . . ?
C5 C6 N1 112.1(9) . . ?
C5 C6 H6A 109.2 . . ?
N1 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
N1 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N1 C7 C8 107.9(10) . . ?
N1 C7 H7A 110.1 . . ?
C8 C7 H7A 110.1 . . ?
N1 C7 H7B 110.1 . . ?
C8 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
N3 C8 C7 120.6(12) . . ?
N3 C8 N4 98.3(14) . . ?
C7 C8 N4 141.2(15) . . ?
N4 C10 C11 100.1(13) . . ?
N4 C10 H10 129.9 . . ?
C11 C10 H10 129.9 . . ?
C10 C11 N3 114.7(12) . . ?
C10 C11 H11 122.6 . . ?
N3 C11 H11 122.6 . . ?
C13 C12 N1 117.6(8) . . ?
C13 C12 H12A 107.9 . . ?
N1 C12 H12A 107.9 . . ?
C13 C12 H12B 107.9 . . ?
N1 C12 H12B 107.9 . . ?
H12A C12 H12B 107.2 . . ?
C14 C13 C18 118.3(9) . . ?
C14 C13 C12 118.9(8) . . ?
C18 C13 C12 121.9(8) . . ?
C15 C14 C13 122.5(9) . . ?
C15 C14 H14 118.7 . . ?
C13 C14 H14 118.7 . . ?
C14 C15 C16 118.6(9) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C17 C16 C15 119.6(10) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C18 C17 C16 123.1(10) . . ?
C18 C17 H17 118.4 . . ?
C16 C17 H17 118.4 . . ?
O1 C18 C17 124.5(9) . . ?
O1 C18 C13 117.6(9) . . ?
C17 C18 C13 117.9(9) . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
O1 Cu1 N1 C6 -67(3) 3_667 . . . ?
N3 Cu1 N1 C6 150.9(9) . . . . ?
N2 Cu1 N1 C6 -6.6(8) . . . . ?
O1 Cu1 N1 C6 -104.3(8) . . . . ?
O1 Cu1 N1 C7 172(3) 3_667 . . . ?
N3 Cu1 N1 C7 29.4(8) . . . . ?
N2 Cu1 N1 C7 -128.1(8) . . . . ?
O1 Cu1 N1 C7 134.2(8) . . . . ?
O1 Cu1 N1 C12 56(3) 3_667 . . . ?
N3 Cu1 N1 C12 -86.5(7) . . . . ?
N2 Cu1 N1 C12 116.1(7) . . . . ?
O1 Cu1 N1 C12 18.4(7) . . . . ?
O1 Cu1 N3 C8 168.2(7) 3_667 . . . ?
N2 Cu1 N3 C8 42.0(12) . . . . ?
N1 Cu1 N3 C8 -15.9(8) . . . . ?
O1 Cu1 N3 C8 -106.8(8) . . . . ?
O1 Cu1 N3 C11 -12.9(11) 3_667 . . . ?
N2 Cu1 N3 C11 -139.0(10) . . . . ?
N1 Cu1 N3 C11 163.0(11) . . . . ?
O1 Cu1 N3 C11 72.1(11) . . . . ?
O1 Cu1 O1 C18 -150.2(9) 3_667 . . . ?
N3 Cu1 O1 C18 109.5(8) . . . . ?
N2 Cu1 O1 C18 -57.0(8) . . . . ?
N1 Cu1 O1 C18 25.8(8) . . . . ?
O1 Cu1 O1 Cu1 0.0 3_667 . . 3_667 ?
N3 Cu1 O1 Cu1 -100.4(4) . . . 3_667 ?
N2 Cu1 O1 Cu1 93.2(3) . . . 3_667 ?
N1 Cu1 O1 Cu1 175.9(4) . . . 3_667 ?
O1 Cu1 N2 C1 0.9(5) 3_667 . . . ?
N3 Cu1 N2 C1 128.5(7) . . . . ?
N1 Cu1 N2 C1 -173.4(5) . . . . ?
O1 Cu1 N2 C1 -81.8(5) . . . . ?
O1 Cu1 N2 C5 172.5(4) 3_667 . . . ?
N3 Cu1 N2 C5 -59.9(8) . . . . ?
N1 Cu1 N2 C5 -1.8(4) . . . . ?
O1 Cu1 N2 C5 89.9(4) . . . . ?
C5 N2 C1 C2 0.0 . . . . ?
Cu1 N2 C1 C2 171.0(6) . . . . ?
N2 C1 C2 C3 0.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 175.9(10) . . . . ?
C3 C4 C5 N2 0.0 . . . . ?
C1 N2 C5 C6 -175.7(10) . . . . ?
Cu1 N2 C5 C6 11.8(10) . . . . ?
C1 N2 C5 C4 0.0 . . . . ?
Cu1 N2 C5 C4 -172.5(5) . . . . ?
C4 C5 C6 N1 166.5(8) . . . . ?
N2 C5 C6 N1 -17.8(15) . . . . ?
C7 N1 C6 C5 130.8(11) . . . . ?
C12 N1 C6 C5 -107.5(11) . . . . ?
Cu1 N1 C6 C5 14.1(13) . . . . ?
C6 N1 C7 C8 -155.8(9) . . . . ?
C12 N1 C7 C8 80.7(10) . . . . ?
Cu1 N1 C7 C8 -36.0(11) . . . . ?
C11 N3 C8 C7 178.6(10) . . . . ?
Cu1 N3 C8 C7 -2.1(14) . . . . ?
C11 N3 C8 N4 -0.2(12) . . . . ?
Cu1 N3 C8 N4 179.1(7) . . . . ?
N1 C7 C8 N3 27.5(15) . . . . ?
N1 C7 C8 N4 -154.4(14) . . . . ?
C10 N4 C8 N3 0.3(14) . . . . ?
C9 N4 C8 N3 178.8(12) . . . . ?
C10 N4 C8 C7 -178.0(15) . . . . ?
C9 N4 C8 C7 0(2) . . . . ?
C9 N4 C10 C11 -178.5(16) . . . . ?
C8 N4 C10 C11 -0.3(14) . . . . ?
N4 C10 C11 N3 0.2(13) . . . . ?
C8 N3 C11 C10 0.0(14) . . . . ?
Cu1 N3 C11 C10 -179.0(8) . . . . ?
C6 N1 C12 C13 60.2(12) . . . . ?
C7 N1 C12 C13 -175.5(10) . . . . ?
Cu1 N1 C12 C13 -61.8(10) . . . . ?
N1 C12 C13 C14 -123.3(10) . . . . ?
N1 C12 C13 C18 68.2(13) . . . . ?
C18 C13 C14 C15 0.0(15) . . . . ?
C12 C13 C14 C15 -168.9(10) . . . . ?
C13 C14 C15 C16 0.7(16) . . . . ?
C14 C15 C16 C17 -0.6(16) . . . . ?
C15 C16 C17 C18 -0.2(18) . . . . ?
Cu1 O1 C18 C17 9.3(16) 3_667 . . . ?
Cu1 O1 C18 C17 149.2(9) . . . . ?
Cu1 O1 C18 C13 -171.4(7) 3_667 . . . ?
Cu1 O1 C18 C13 -31.5(12) . . . . ?
C16 C17 C18 O1 -179.7(10) . . . . ?
C16 C17 C18 C13 1.0(17) . . . . ?
C14 C13 C18 O1 179.7(9) . . . . ?
C12 C13 C18 O1 -11.7(14) . . . . ?
C14 C13 C18 C17 -0.9(14) . . . . ?
C12 C13 C18 C17 167.7(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.865
_refine_diff_density_min         -0.889
_refine_diff_density_rms         0.154
