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


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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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#  fide research purposes only. It may contain copyright material 
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data_Complex_1
_database_code_depnum_ccdc_archive 'CCDC 905660'
#TrackingRef '14641_web_deposit_cif_file_0_AdailtonJ.Bortoluzzi_1349982265.Deposit_CCDC.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H34 Cl3 Cu2 N3 O2'
_chemical_formula_sum            'C21 H34 Cl3 Cu2 N3 O2'
_chemical_formula_weight         593.94
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   'C c'
_symmetry_space_group_name_Hall  'C -2yc'
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'
_cell_length_a                   13.1157(8)
_cell_length_b                   16.0029(10)
_cell_length_c                   12.0041(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.323(12)
_cell_angle_gamma                90.00
_cell_volume                     2512.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      8.36
_cell_measurement_theta_max      15.36
_exptl_crystal_description       'irregular block'
_exptl_crystal_colour            black-brownish
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1224
_exptl_absorpt_coefficient_mu    2.035
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.374
_exptl_absorpt_correction_T_max  0.441
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       \w--2\q
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        1
_diffrn_reflns_number            4274
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3406
_reflns_number_gt                3127
_reflns_threshold_expression     >2\s(I)
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+1.5406P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(13)
_refine_ls_number_reflns         3406
_refine_ls_number_parameters     280
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0784
_refine_ls_wR_factor_gt          0.0751
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_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 0.39694(4) 0.22517(3) 0.19085(4) 0.02842(12) Uani 1 1 d . . .
Cu2 Cu 0.17292(4) 0.14108(3) 0.20020(4) 0.02965(13) Uani 1 1 d . . .
Cl1 Cl 0.30292(10) 0.15878(8) 0.04936(10) 0.0471(3) Uani 1 1 d . . .
Cl2 Cl 0.04538(10) 0.08369(7) 0.09671(11) 0.0469(3) Uani 1 1 d . . .
Cl3 Cl 0.11436(12) 0.27233(8) 0.21397(17) 0.0651(5) Uani 1 1 d . . .
O10 O 0.2997(2) 0.17004(19) 0.2855(2) 0.0313(6) Uani 1 1 d . . .
O18 O 0.1880(2) 0.02752(18) 0.2930(3) 0.0360(7) Uani 1 1 d . . .
N1 N 0.4521(3) 0.2985(2) 0.3201(3) 0.0300(8) Uani 1 1 d . . .
C2 C 0.4728(4) 0.3799(3) 0.2675(4) 0.0350(10) Uani 1 1 d . . .
H2A H 0.5129 0.4146 0.3205 0.042 Uiso 1 1 calc R . .
H2B H 0.4086 0.4082 0.2478 0.042 Uiso 1 1 calc R . .
C3 C 0.5299(4) 0.3682(3) 0.1642(4) 0.0382(11) Uani 1 1 d . . .
H3A H 0.5280 0.4198 0.1217 0.046 Uiso 1 1 calc R . .
H3B H 0.6009 0.3551 0.1857 0.046 Uiso 1 1 calc R . .
N4 N 0.4837(3) 0.2995(2) 0.0930(3) 0.0361(8) Uani 1 1 d . . .
C4 C 0.4206(4) 0.3330(3) -0.0080(4) 0.0486(13) Uani 1 1 d . . .
H4 H 0.3908 0.2845 -0.0484 0.058 Uiso 1 1 calc R . .
C5 C 0.5638(4) 0.2410(3) 0.0585(4) 0.0462(12) Uani 1 1 d . . .
H5A H 0.6146 0.2724 0.0214 0.055 Uiso 1 1 calc R . .
H5B H 0.5328 0.2012 0.0052 0.055 Uiso 1 1 calc R . .
C6 C 0.6167(4) 0.1935(3) 0.1565(5) 0.0473(12) Uani 1 1 d . . .
H6A H 0.6629 0.1528 0.1280 0.057 Uiso 1 1 calc R . .
H6B H 0.6574 0.2324 0.2032 0.057 Uiso 1 1 calc R . .
N7 N 0.5458(3) 0.1504(2) 0.2252(4) 0.0389(9) Uani 1 1 d . . .
C7 C 0.5451(5) 0.0566(3) 0.2089(6) 0.0577(15) Uani 1 1 d . . .
H7 H 0.4873 0.0355 0.2479 0.069 Uiso 1 1 calc R . .
C8 C 0.5631(4) 0.1702(3) 0.3452(5) 0.0424(11) Uani 1 1 d . . .
H8A H 0.6322 0.1539 0.3706 0.051 Uiso 1 1 calc R . .
H8B H 0.5166 0.1370 0.3861 0.051 Uiso 1 1 calc R . .
C9 C 0.5484(3) 0.2618(3) 0.3735(4) 0.0367(10) Uani 1 1 d . . .
H9A H 0.5480 0.2675 0.4539 0.044 Uiso 1 1 calc R . .
H9B H 0.6062 0.2934 0.3500 0.044 Uiso 1 1 calc R . .
C10 C 0.3740(3) 0.3105(3) 0.4006(4) 0.0311(9) Uani 1 1 d . . .
H10A H 0.3124 0.3322 0.3613 0.037 Uiso 1 1 calc R . .
H10B H 0.3984 0.3520 0.4552 0.037 Uiso 1 1 calc R . .
C11 C 0.3479(3) 0.2326(3) 0.4607(4) 0.0298(9) Uani 1 1 d . . .
C12 C 0.3051(3) 0.1657(3) 0.3963(3) 0.0273(8) Uani 1 1 d . . .
C13 C 0.2706(3) 0.0947(3) 0.4517(4) 0.0296(9) Uani 1 1 d . . .
C14 C 0.2862(3) 0.0894(3) 0.5689(4) 0.0355(10) Uani 1 1 d . . .
H14 H 0.2648 0.0417 0.6047 0.043 Uiso 1 1 calc R . .
C15 C 0.3319(4) 0.1522(3) 0.6315(4) 0.0381(11) Uani 1 1 d . . .
C16 C 0.3611(3) 0.2242(3) 0.5761(4) 0.0356(10) Uani 1 1 d . . .
H16 H 0.3904 0.2681 0.6181 0.043 Uiso 1 1 calc R . .
C17 C 0.2200(3) 0.0271(3) 0.3913(4) 0.0321(9) Uani 1 1 d . . .
H17 H 0.2107 -0.0219 0.4310 0.039 Uiso 1 1 calc R . .
C19 C 0.3518(5) 0.1468(4) 0.7567(4) 0.0559(15) Uani 1 1 d . . .
H19A H 0.3853 0.1969 0.7840 0.084 Uiso 1 1 calc R . .
H19B H 0.3947 0.0995 0.7754 0.084 Uiso 1 1 calc R . .
H19C H 0.2881 0.1406 0.7902 0.084 Uiso 1 1 calc R . .
C41 C 0.3318(5) 0.3859(4) 0.0266(5) 0.0616(16) Uani 1 1 d . . .
H41A H 0.2934 0.3548 0.0776 0.092 Uiso 1 1 calc R . .
H41B H 0.2881 0.4003 -0.0383 0.092 Uiso 1 1 calc R . .
H41C H 0.3578 0.4360 0.0624 0.092 Uiso 1 1 calc R . .
C42 C 0.4821(6) 0.3809(4) -0.0900(5) 0.0658(17) Uani 1 1 d . . .
H42A H 0.5370 0.3465 -0.1121 0.099 Uiso 1 1 calc R . .
H42B H 0.5097 0.4308 -0.0548 0.099 Uiso 1 1 calc R . .
H42C H 0.4384 0.3958 -0.1547 0.099 Uiso 1 1 calc R . .
C71 C 0.5234(6) 0.0322(4) 0.0859(7) 0.088(2) Uani 1 1 d . . .
H71A H 0.4616 0.0589 0.0564 0.132 Uiso 1 1 calc R . .
H71B H 0.5157 -0.0273 0.0801 0.132 Uiso 1 1 calc R . .
H71C H 0.5793 0.0498 0.0443 0.132 Uiso 1 1 calc R . .
C72 C 0.6394(7) 0.0129(4) 0.2618(8) 0.096(3) Uani 1 1 d . . .
H72A H 0.6497 0.0287 0.3390 0.144 Uiso 1 1 calc R . .
H72B H 0.6980 0.0288 0.2235 0.144 Uiso 1 1 calc R . .
H72C H 0.6301 -0.0465 0.2565 0.144 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0321(2) 0.0297(2) 0.0239(2) -0.0032(2) 0.00483(19) -0.0093(2)
Cu2 0.0325(3) 0.0274(2) 0.0282(2) -0.0008(2) -0.0034(2) -0.0045(2)
Cl1 0.0586(8) 0.0576(8) 0.0260(5) -0.0103(5) 0.0086(5) -0.0291(6)
Cl2 0.0505(7) 0.0340(6) 0.0522(7) 0.0069(5) -0.0232(6) -0.0088(5)
Cl3 0.0554(8) 0.0334(6) 0.1047(14) -0.0110(7) -0.0056(8) 0.0073(5)
O10 0.0322(15) 0.0412(16) 0.0203(14) 0.0004(12) 0.0010(12) -0.0118(13)
O18 0.0429(17) 0.0286(15) 0.0355(17) -0.0005(13) -0.0044(14) -0.0003(12)
N1 0.0330(19) 0.0273(17) 0.0298(18) -0.0014(14) 0.0031(15) -0.0058(14)
C2 0.041(2) 0.025(2) 0.039(3) -0.0030(18) 0.002(2) -0.0065(17)
C3 0.045(3) 0.032(2) 0.038(3) 0.0007(19) 0.006(2) -0.0116(19)
N4 0.041(2) 0.0367(19) 0.0313(19) -0.0032(16) 0.0095(17) -0.0135(16)
C4 0.061(3) 0.049(3) 0.036(3) 0.003(2) 0.000(2) -0.025(3)
C5 0.051(3) 0.051(3) 0.040(3) -0.009(2) 0.024(2) -0.016(2)
C6 0.040(3) 0.044(3) 0.060(3) -0.010(2) 0.016(2) -0.006(2)
N7 0.037(2) 0.033(2) 0.048(2) -0.0073(17) 0.0094(19) -0.0019(16)
C7 0.061(3) 0.037(3) 0.076(4) -0.010(3) 0.015(3) -0.001(3)
C8 0.039(3) 0.038(2) 0.049(3) 0.002(2) 0.000(2) 0.0054(19)
C9 0.032(2) 0.042(2) 0.036(2) -0.001(2) -0.0023(19) -0.0048(19)
C10 0.034(2) 0.032(2) 0.028(2) -0.0074(17) 0.0016(17) -0.0041(17)
C11 0.025(2) 0.039(2) 0.026(2) -0.0036(17) 0.0041(16) -0.0009(17)
C12 0.0215(19) 0.038(2) 0.0228(19) -0.0015(17) 0.0036(15) 0.0013(16)
C13 0.027(2) 0.033(2) 0.029(2) 0.0024(17) 0.0042(17) -0.0003(16)
C14 0.036(2) 0.043(2) 0.028(2) 0.0087(19) 0.0043(18) -0.0035(19)
C15 0.036(2) 0.055(3) 0.024(2) -0.002(2) 0.0028(19) -0.003(2)
C16 0.031(2) 0.048(3) 0.029(2) -0.0078(19) 0.0042(18) -0.0073(19)
C17 0.034(2) 0.029(2) 0.033(2) 0.0026(17) 0.0006(19) 0.0004(16)
C19 0.069(4) 0.076(4) 0.023(2) 0.002(2) 0.001(2) -0.019(3)
C41 0.060(4) 0.066(4) 0.056(4) 0.022(3) -0.007(3) -0.009(3)
C42 0.095(5) 0.062(4) 0.042(3) 0.007(3) 0.014(3) -0.026(3)
C71 0.083(5) 0.064(4) 0.117(7) -0.037(4) 0.015(5) -0.009(4)
C72 0.110(6) 0.048(4) 0.125(7) -0.021(4) -0.026(5) 0.030(4)
_geom_special_details            
;
;
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 O10 1.978(3) . y
Cu1 N1 2.035(4) . y
Cu1 N4 2.071(4) . y
Cu1 Cl1 2.2844(12) . y
Cu1 N7 2.300(4) . y
Cu2 O10 1.943(3) . y
Cu2 O18 2.133(3) . y
Cu2 Cl2 2.2071(12) . y
Cu2 Cl3 2.2468(13) . y
Cu2 Cl1 2.5945(14) . y
O10 C12 1.328(5) . ?
O18 C17 1.223(5) . ?
N1 C10 1.473(6) . ?
N1 C2 1.480(5) . ?
N1 C9 1.493(6) . ?
C2 C3 1.508(7) . ?
C3 N4 1.493(6) . ?
N4 C5 1.490(7) . ?
N4 C4 1.513(7) . ?
C4 C41 1.524(9) . ?
C4 C42 1.526(8) . ?
C5 C6 1.523(8) . ?
C6 N7 1.461(6) . ?
N7 C8 1.476(7) . ?
N7 C7 1.515(6) . ?
C7 C72 1.517(9) . ?
C7 C71 1.533(10) . ?
C8 C9 1.520(7) . ?
C10 C11 1.492(6) . ?
C11 C16 1.390(6) . ?
C11 C12 1.413(6) . ?
C12 C13 1.408(6) . ?
C13 C14 1.408(6) . ?
C13 C17 1.437(6) . ?
C14 C15 1.366(7) . ?
C15 C16 1.398(7) . ?
C15 C19 1.508(7) . ?
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
O10 Cu1 N1 91.56(13) . . y
O10 Cu1 N4 170.80(15) . . y
N1 Cu1 N4 85.51(15) . . y
O10 Cu1 Cl1 83.37(9) . . y
N1 Cu1 Cl1 167.52(11) . . y
N4 Cu1 Cl1 97.72(11) . . y
O10 Cu1 N7 103.89(14) . . y
N1 Cu1 N7 85.12(14) . . y
N4 Cu1 N7 84.57(16) . . y
Cl1 Cu1 N7 107.14(11) . . y
O10 Cu2 O18 83.46(12) . . y
O10 Cu2 Cl2 168.10(10) . . y
O18 Cu2 Cl2 88.61(9) . . y
O10 Cu2 Cl3 91.27(10) . . y
O18 Cu2 Cl3 140.98(11) . . y
Cl2 Cu2 Cl3 100.46(6) . . y
O10 Cu2 Cl1 76.13(9) . . y
O18 Cu2 Cl1 114.68(10) . . y
Cl2 Cu2 Cl1 99.36(5) . . y
Cl3 Cu2 Cl1 101.28(6) . . y
Cu1 Cl1 Cu2 83.00(4) . . y
C12 O10 Cu2 119.6(3) . . ?
C12 O10 Cu1 127.7(2) . . ?
Cu2 O10 Cu1 111.52(14) . . y
C17 O18 Cu2 121.4(3) . . ?
C10 N1 C2 108.9(3) . . ?
C10 N1 C9 112.1(4) . . ?
C2 N1 C9 110.7(3) . . ?
C10 N1 Cu1 110.5(3) . . ?
C2 N1 Cu1 104.4(3) . . ?
C9 N1 Cu1 110.0(3) . . ?
N1 C2 C3 111.1(4) . . ?
N4 C3 C2 110.9(4) . . ?
C5 N4 C3 110.9(4) . . ?
C5 N4 C4 110.7(4) . . ?
C3 N4 C4 111.8(4) . . ?
C5 N4 Cu1 103.1(3) . . ?
C3 N4 Cu1 108.4(3) . . ?
C4 N4 Cu1 111.6(3) . . ?
N4 C4 C41 111.2(4) . . ?
N4 C4 C42 114.3(5) . . ?
C41 C4 C42 110.4(5) . . ?
N4 C5 C6 112.9(4) . . ?
N7 C6 C5 113.5(4) . . ?
C6 N7 C8 113.1(4) . . ?
C6 N7 C7 113.1(4) . . ?
C8 N7 C7 109.7(4) . . ?
C6 N7 Cu1 102.8(3) . . ?
C8 N7 Cu1 97.4(3) . . ?
C7 N7 Cu1 119.7(3) . . ?
N7 C7 C72 114.0(5) . . ?
N7 C7 C71 112.0(5) . . ?
C72 C7 C71 111.9(6) . . ?
N7 C8 C9 114.3(4) . . ?
N1 C9 C8 113.6(4) . . ?
N1 C10 C11 113.9(4) . . ?
C16 C11 C12 119.1(4) . . ?
C16 C11 C10 123.2(4) . . ?
C12 C11 C10 117.7(4) . . ?
O10 C12 C13 121.4(4) . . ?
O10 C12 C11 119.8(4) . . ?
C13 C12 C11 118.8(4) . . ?
C14 C13 C12 119.5(4) . . ?
C14 C13 C17 119.0(4) . . ?
C12 C13 C17 121.4(4) . . ?
C15 C14 C13 122.0(4) . . ?
C14 C15 C16 118.0(4) . . ?
C14 C15 C19 122.8(5) . . ?
C16 C15 C19 119.2(4) . . ?
C11 C16 C15 122.4(4) . . ?
O18 C17 C13 126.5(4) . . ?
_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.077