# Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2000
# CCDC Number: 186/2012

data_1

_audit_creation_method            SHELXL
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_formula_moiety          ?
_chemical_formula_structural      ?
_chemical_formula_analytical      ?
_chemical_formula_sum
 'C1456 H26 Cu1 N4 O4'
_chemical_formula_weight          377.93
_chemical_melting_point           ?
_chemical_compound_source         ?

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            ?
_symmetry_space_group_name_H-M    ?

loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, z'
 '-x+1/4, y+1/4, z+1/4'
 'x+1/4, -y+1/4, z+1/4'
 'x, y+1/2, z+1/2'
 '-x, -y+1/2, z+1/2'
 '-x+1/4, y+3/4, z+3/4'
 'x+1/4, -y+3/4, z+3/4'
 'x+1/2, y, z+1/2'
 '-x+1/2, -y, z+1/2'
 '-x+3/4, y+1/4, z+3/4'
 'x+3/4, -y+1/4, z+3/4'
 'x+1/2, y+1/2, z'
 '-x+1/2, -y+1/2, z'
 '-x+3/4, y+3/4, z+1/4'
 'x+3/4, -y+3/4, z+1/4'

_cell_length_a                    24.419(5)
_cell_length_b                    31.207(5)
_cell_length_c                    8.475(5)
_cell_angle_alpha                 90.000(5)
_cell_angle_beta                  90.000(5)
_cell_angle_gamma                 90.000(5)
_cell_volume                      6458(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?

_exptl_crystal_description        ?
_exptl_crystal_colour             ?
_exptl_crystal_size_max           ?
_exptl_crystal_size_mid           ?
_exptl_crystal_size_min           ?
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.538
_exptl_crystal_density_method     ?
_exptl_crystal_F_000              3120
_exptl_absorpt_coefficient_mu     1.378
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?

_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        ?
_diffrn_measurement_method        ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             1962
_diffrn_reflns_av_R_equivalents   0.0000
_diffrn_reflns_av_sigmaI/netI     0.0275
_diffrn_reflns_limit_h_min        0
_diffrn_reflns_limit_h_max        31
_diffrn_reflns_limit_k_min        0
_diffrn_reflns_limit_k_max        40
_diffrn_reflns_limit_l_min        0
_diffrn_reflns_limit_l_max        10
_diffrn_reflns_theta_min          2.61
_diffrn_reflns_theta_max          27.46
_reflns_number_total              1962
_reflns_number_observed           1832
_reflns_observed_criterion        >2sigma(I)

_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXS-96 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-96 (Sheldrick, 1996)'
_computing_molecular_graphics     ?
_computing_publication_material   ?

_refine_special_details
;
 Refinement of F^2^ against ALL reflections.  Weighted R-factors wR and all
 goodnesses of fit S are based on F^2^, conventional R-factors R
 are based on F, with F set to zero for negative F^2^. The observed criterion
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme
 'calc w=1/[\s^2^(Fo^2^)+(0.0626P)^2^+1.8971P] 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     ?
_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(17)
_refine_ls_number_reflns          1962
_refine_ls_number_parameters      212
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0372
_refine_ls_R_factor_obs           0.0318
_refine_ls_wR_factor_all          0.0864
_refine_ls_wR_factor_obs          0.0835
_refine_ls_goodness_of_fit_all    1.071
_refine_ls_goodness_of_fit_obs    1.076
_refine_ls_restrained_S_all       1.071
_refine_ls_restrained_S_obs       1.076
_refine_ls_shift/esd_max          0.243
_refine_ls_shift/esd_mean         0.055

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_thermal_displace_type
 _atom_site_occupancy
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_group
Cu1 Cu 0.654280(15) 0.384285(12) 0.36468(6) 0.02027(13) Uani 1 d . .
N1 N 0.64777(14) 0.43211(11) 0.1556(4) 0.0288(7) Uani 1 d . .
N2 N 0.68591(12) 0.34410(10) 0.1879(4) 0.0237(6) Uani 1 d . .
N3 N 0.70374(14) 0.33732(10) 0.5184(4) 0.0295(7) Uani 1 d . .
N4 N 0.72165(12) 0.42563(10) 0.4204(4) 0.0240(6) Uani 1 d . .
O1 O 0.58360(11) 0.35683(9) 0.3086(4) 0.0312(6) Uani 1 d . .
O2 O 0.61728(11) 0.41532(9) 0.5339(4) 0.0328(6) Uani 1 d . .
O3 O 0.54470(11) 0.31237(10) 0.1361(5) 0.0440(8) Uani 1 d . .
O4 O 0.62013(13) 0.47335(11) 0.6832(5) 0.0483(8) Uani 1 d . .
C1 C 0.65626(18) 0.40424(15) 0.0174(5) 0.0357(9) Uani 1 d . .
H1A H 0.6677 0.4217 -0.0714 0.040(3) Uiso 1 calc R .
H1B H 0.6218 0.3908 -0.0103 0.040(3) Uiso 1 calc R .
C2 C 0.69862(17) 0.36995(13) 0.0464(5) 0.0320(8) Uani 1 d . .
H2A H 0.7005 0.3513 -0.0449 0.040(3) Uiso 1 calc R .
H2B H 0.7342 0.3833 0.0595 0.040(3) Uiso 1 calc R .
C3 C 0.73574(15) 0.32159(13) 0.2437(5) 0.0320(9) Uani 1 d . .
H3A H 0.7668 0.3409 0.2384 0.040(3) Uiso 1 calc R .
H3B H 0.7432 0.2974 0.1749 0.040(3) Uiso 1 calc R .
C4 C 0.72892(18) 0.30565(13) 0.4128(6) 0.0374(10) Uani 1 d . .
H4A H 0.7065 0.2800 0.4119 0.040(3) Uiso 1 calc R .
H4B H 0.7646 0.2979 0.4542 0.040(3) Uiso 1 calc R .
C5 C 0.74389(18) 0.36552(13) 0.5976(7) 0.0396(11) Uani 1 d . .
H5A H 0.7738 0.3482 0.6378 0.040(3) Uiso 1 calc R .
H5B H 0.7264 0.3794 0.6868 0.040(3) Uiso 1 calc R .
C6 C 0.76671(15) 0.39941(13) 0.4885(6) 0.0325(9) Uani 1 d . .
H6A H 0.7916 0.4178 0.5465 0.040(3) Uiso 1 calc R .
H6B H 0.7871 0.3858 0.4040 0.040(3) Uiso 1 calc R .
C7 C 0.73976(16) 0.44792(13) 0.2758(5) 0.0322(8) Uani 1 d . .
C8 C 0.6916(2) 0.46453(15) 0.1790(6) 0.0390(10) Uani 1 d . .
C9 C 0.59410(19) 0.45346(17) 0.1450(8) 0.0499(14) Uani 1 d . .
H9A H 0.5884 0.4707 0.2374 0.048(6) Uiso 1 calc R .
H9B H 0.5658 0.4322 0.1377 0.048(6) Uiso 1 calc R .
H9C H 0.5932 0.4714 0.0530 0.048(6) Uiso 1 calc R .
C10 C 0.6691(2) 0.31595(17) 0.6377(6) 0.0476(12) Uani 1 d . .
H10A H 0.6907 0.2958 0.6963 0.048(6) Uiso 1 calc R .
H10B H 0.6396 0.3012 0.5860 0.048(6) Uiso 1 calc R .
H10C H 0.6543 0.3370 0.7084 0.048(6) Uiso 1 calc R .
C11 C 0.64147(15) 0.31304(12) 0.1529(5) 0.0304(9) Uani 1 d . .
H11A H 0.6490 0.2865 0.2084 0.040(3) Uiso 1 calc R .
H11B H 0.6417 0.3068 0.0407 0.040(3) Uiso 1 calc R .
C12 C 0.58491(15) 0.32870(12) 0.1992(5) 0.0263(7) Uani 1 d . .
C13 C 0.64099(17) 0.44799(13) 0.5897(5) 0.0282(8) Uani 1 d . .
C14 C 0.69993(17) 0.45632(13) 0.5405(5) 0.0297(8) Uani 1 d . .
H14A H 0.7025 0.4851 0.4982 0.040(3) Uiso 1 calc R .
H14B H 0.7230 0.4550 0.6335 0.040(3) Uiso 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 0.02041(18) 0.02083(19) 0.01956(19) -0.00327(17) 0.00205(16) -0.00180(15)
N1 0.0319(15) 0.0255(16) 0.0291(19) -0.0003(14) -0.0028(13) -0.0029(13)
N2 0.0210(13) 0.0228(15) 0.0273(16) -0.0050(13) 0.0036(13) -0.0030(12)
N3 0.0356(17) 0.0232(16) 0.0299(18) 0.0005(14) -0.0039(15) -0.0033(13)
N4 0.0247(13) 0.0217(13) 0.0256(16) -0.0039(12) 0.0037(12) -0.0020(12)
O1 0.0235(11) 0.0308(13) 0.0392(16) -0.0086(13) 0.0081(12) -0.0045(10)
O2 0.0285(13) 0.0340(15) 0.0359(16) -0.0118(13) 0.0091(13) -0.0047(11)
O3 0.0300(13) 0.0436(17) 0.058(2) -0.0153(18) -0.0051(15) -0.0064(12)
O4 0.0445(16) 0.0447(18) 0.056(2) -0.0240(17) 0.0118(17) 0.0040(14)
C1 0.048(2) 0.038(2) 0.0210(19) 0.0002(18) -0.0029(17) -0.0077(19)
C2 0.037(2) 0.036(2) 0.0230(19) -0.0063(17) 0.0083(17) -0.0054(16)
C3 0.0236(16) 0.031(2) 0.041(2) -0.0121(18) 0.0032(17) 0.0069(15)
C4 0.042(2) 0.0222(18) 0.047(3) 0.0011(18) -0.0070(19) 0.0086(16)
C5 0.046(2) 0.0305(19) 0.042(3) 0.0002(19) -0.024(2) -0.0012(17)
C6 0.0248(15) 0.0322(19) 0.040(2) -0.0078(19) -0.0073(16) -0.0019(14)
C7 0.0342(19) 0.032(2) 0.030(2) 0.0007(17) 0.0066(17) -0.0118(16)
C8 0.047(2) 0.031(2) 0.039(2) 0.0076(19) -0.007(2) -0.0146(19)
C9 0.046(2) 0.042(2) 0.061(4) 0.003(3) -0.009(2) 0.012(2)
C10 0.065(3) 0.048(3) 0.030(3) 0.007(2) 0.000(2) -0.012(2)
C11 0.0293(16) 0.0253(17) 0.036(3) -0.0131(17) 0.0042(16) -0.0045(14)
C12 0.0274(16) 0.0222(16) 0.029(2) 0.0000(15) 0.0018(15) -0.0045(14)
C13 0.0316(16) 0.0300(19) 0.023(2) -0.0053(16) -0.0007(16) 0.0070(16)
C14 0.0363(19) 0.0229(18) 0.030(2) -0.0092(16) 0.0061(17) -0.0045(15)

_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 O2 1.952(3) . ?
Cu1 O1 1.985(3) . ?
Cu1 N2 2.101(3) . ?
Cu1 N4 2.143(3) . ?
Cu1 N3 2.303(3) . ?
Cu1 N1 2.322(4) . ?
N1 C1 1.473(6) . ?
N1 C9 1.473(5) . ?
N1 C8 1.486(5) . ?
N2 C2 1.478(5) . ?
N2 C3 1.483(5) . ?
N2 C11 1.485(5) . ?
N3 C4 1.468(5) . ?
N3 C10 1.478(6) . ?
N3 C5 1.479(5) . ?
N4 C7 1.477(5) . ?
N4 C6 1.488(5) . ?
N4 C14 1.495(5) . ?
O1 C12 1.277(5) . ?
O2 C13 1.264(5) . ?
O3 C12 1.229(5) . ?
O4 C13 1.230(5) . ?
C1 C2 1.509(6) . ?
C3 C4 1.526(7) . ?
C5 C6 1.511(7) . ?
C7 C8 1.525(6) . ?
C11 C12 1.517(5) . ?
C13 C14 1.521(5) . ?

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
O2 Cu1 O1 89.29(12) . . ?
O2 Cu1 N2 171.96(12) . . ?
O1 Cu1 N2 83.75(12) . . ?
O2 Cu1 N4 83.96(11) . . ?
O1 Cu1 N4 168.55(12) . . ?
N2 Cu1 N4 103.55(11) . . ?
O2 Cu1 N3 98.21(13) . . ?
O1 Cu1 N3 108.47(12) . . ?
N2 Cu1 N3 80.26(14) . . ?
N4 Cu1 N3 81.72(12) . . ?
O2 Cu1 N1 102.13(13) . . ?
O1 Cu1 N1 92.01(13) . . ?
N2 Cu1 N1 82.21(13) . . ?
N4 Cu1 N1 80.43(12) . . ?
N3 Cu1 N1 151.23(12) . . ?
C1 N1 C9 110.1(4) . . ?
C1 N1 C8 114.0(4) . . ?
C9 N1 C8 109.9(4) . . ?
C1 N1 Cu1 102.6(2) . . ?
C9 N1 Cu1 113.4(3) . . ?
C8 N1 Cu1 106.6(3) . . ?
C2 N2 C3 110.2(3) . . ?
C2 N2 C11 110.3(3) . . ?
C3 N2 C11 110.7(3) . . ?
C2 N2 Cu1 109.3(2) . . ?
C3 N2 Cu1 110.9(3) . . ?
C11 N2 Cu1 105.3(2) . . ?
C4 N3 C10 110.7(3) . . ?
C4 N3 C5 113.5(4) . . ?
C10 N3 C5 109.8(4) . . ?
C4 N3 Cu1 107.6(3) . . ?
C10 N3 Cu1 111.9(3) . . ?
C5 N3 Cu1 103.0(2) . . ?
C7 N4 C6 111.1(3) . . ?
C7 N4 C14 111.7(3) . . ?
C6 N4 C14 110.5(3) . . ?
C7 N4 Cu1 109.3(2) . . ?
C6 N4 Cu1 108.8(2) . . ?
C14 N4 Cu1 105.3(2) . . ?
C12 O1 Cu1 116.7(2) . . ?
C13 O2 Cu1 117.6(2) . . ?
N1 C1 C2 112.7(4) . . ?
N2 C2 C1 112.0(3) . . ?
N2 C3 C4 111.4(3) . . ?
N3 C4 C3 113.5(3) . . ?
N3 C5 C6 112.5(4) . . ?
N4 C6 C5 110.5(3) . . ?
N4 C7 C8 112.1(3) . . ?
N1 C8 C7 113.3(4) . . ?
N2 C11 C12 113.8(3) . . ?
O3 C12 O1 125.5(4) . . ?
O3 C12 C11 118.8(4) . . ?
O1 C12 C11 115.6(3) . . ?
O4 C13 O2 124.7(4) . . ?
O4 C13 C14 117.3(4) . . ?
O2 C13 C14 118.0(3) . . ?
N4 C14 C13 114.4(3) . . ?

_refine_diff_density_max    0.556
_refine_diff_density_min   -0.632
_refine_diff_density_rms    0.133