# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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 1016461'
_audit_update_record             
;
2014-07-28 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H30 Cl2 Cu2 N6 O14'
_chemical_formula_weight         800.50

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'
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'
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   P21/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                   8.0418(7)
_cell_length_b                   7.8054(6)
_cell_length_c                   26.761(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.099(4)
_cell_angle_gamma                90.00
_cell_volume                     1642.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    90
_cell_measurement_theta_min      1.65
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    1.529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.730
_exptl_absorpt_correction_T_max  0.736
_exptl_absorpt_process_details   SADABS

_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  'Bruker Apex II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean n/a
_diffrn_standards_number         n/a
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0.0(2)
_diffrn_reflns_number            3761
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0019
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         27.45
_reflns_number_total             3761
_reflns_number_gt                1636
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0237P)²+0.4964P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3761
_refine_ls_number_parameters     212
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0134
_refine_ls_R_factor_gt           0.0133
_refine_ls_wR_factor_ref         0.0469
_refine_ls_wR_factor_gt          0.0464
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_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 0.40417(2) 0.49091(2) 0.953364(16) 0.0289(3) Uani 1 1 d . . .
Cl1 Cl -0.42119(10) 0.01473(9) 0.82150(5) 0.0949(7) Uani 1 1 d . . .
O4 O 0.60052(14) 0.59141(17) 0.92978(8) 0.0411(10) Uani 1 1 d . . .
O1 O 0.2404(2) 0.3927(2) 0.99128(14) 0.040(2) Uani 1 1 d . . .
C1 C 0.37636(19) 0.7906(2) 1.01160(14) 0.0347(15) Uani 1 1 d . . .
O2 O 0.32979(15) 0.72026(16) 0.96911(9) 0.0404(10) Uani 1 1 d . . .
O3 O 0.51440(14) 0.26940(14) 0.95149(8) 0.0423(9) Uani 1 1 d . . .
O7 O -0.3561(4) 0.5259(4) 0.83004(17) 0.1038(16) Uani 1 1 d D . .
O6 O -0.0368(2) 0.8533(2) 0.78944(10) 0.0756(11) Uani 1 1 d . . .
N2 N -0.01440(16) 0.4150(2) 0.82524(10) 0.0350(11) Uani 1 1 d . . .
O5 O -0.1753(2) 0.6467(3) 0.74777(11) 0.0837(13) Uani 1 1 d . . .
C5 C 0.1247(3) 0.1762(2) 0.88131(14) 0.0562(16) Uani 1 1 d . . .
H5A H 0.0293 0.1113 0.8633 0.084 Uiso 1 1 calc R . .
H5B H 0.1247 0.1760 0.9172 0.084 Uiso 1 1 calc R . .
H5C H 0.2282 0.1255 0.8758 0.084 Uiso 1 1 calc R . .
N1 N 0.22562(16) 0.47567(17) 0.87973(11) 0.0321(12) Uani 1 1 d . . .
C2 C 0.2923(2) 0.9562(2) 1.02051(13) 0.0522(15) Uani 1 1 d . . .
H2A H 0.3389 0.9965 1.0545 0.078 Uiso 1 1 calc R . .
H2B H 0.1722 0.9382 1.0167 0.078 Uiso 1 1 calc R . .
H2C H 0.3121 1.0399 0.9961 0.078 Uiso 1 1 calc R . .
N3 N -0.07249(19) 0.7022(2) 0.78389(12) 0.0502(12) Uani 1 1 d . . .
C7 C 0.1706(2) 0.6207(2) 0.85381(13) 0.0374(13) Uani 1 1 d . . .
C9 C -0.1690(2) 0.3177(3) 0.80255(13) 0.0450(14) Uani 1 1 d . . .
H9A H -0.1416 0.1968 0.8019 0.054 Uiso 1 1 calc R . .
H9B H -0.2107 0.3551 0.7676 0.054 Uiso 1 1 calc R . .
C10 C -0.3046(2) 0.3435(3) 0.83256(13) 0.0468(14) Uani 1 1 d . . .
H10 H -0.2592 0.3124 0.8683 0.056 Uiso 1 1 calc R . .
C4 C 0.8864(2) 0.6795(2) 0.93893(13) 0.0524(16) Uani 1 1 d . . .
H4A H 0.9834 0.6991 0.9660 0.079 Uiso 1 1 calc R . .
H4B H 0.8576 0.7835 0.9199 0.079 Uiso 1 1 calc R . .
H4C H 0.9127 0.5918 0.9166 0.079 Uiso 1 1 calc R . .
C6 C 0.11211(19) 0.3543(2) 0.86216(13) 0.0335(14) Uani 1 1 d . . .
C11 C -0.4616(2) 0.2353(3) 0.81206(14) 0.0650(16) Uani 1 1 d . . .
H11A H -0.5002 0.2575 0.7758 0.078 Uiso 1 1 calc R . .
H11B H -0.5520 0.2686 0.8291 0.078 Uiso 1 1 calc R . .
C8 C 0.0226(2) 0.5844(3) 0.82009(13) 0.0375(14) Uani 1 1 d . . .
C3 C 0.7378(3) 0.6230(3) 0.9612(2) 0.035(3) Uani 1 1 d . . .
H6 H -0.298(5) 0.578(5) 0.8117(17) 0.128(19) Uiso 1 1 d 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 O3 1.9485(11) . ?
Cu1 O2 1.9610(14) . ?
Cu1 O1 1.978(3) . ?
Cu1 O4 1.9811(15) . ?
Cu1 N1 2.185(2) . ?
Cu1 Cu1 2.6482(7) 3_667 ?
Cl1 C11 1.761(2) . ?
O4 C3 1.264(3) . ?
O1 C3 1.253(7) 3_667 ?
C1 O2 1.248(3) . ?
C1 O3 1.266(3) 3_667 ?
C1 C2 1.501(2) . ?
O3 C1 1.266(3) 3_667 ?
O7 C10 1.481(3) . ?
O6 N3 1.216(2) . ?
N2 C6 1.347(3) . ?
N2 C8 1.369(3) . ?
N2 C9 1.474(2) . ?
O5 N3 1.213(3) . ?
C5 C6 1.478(3) . ?
N1 C6 1.331(2) . ?
N1 C7 1.353(3) . ?
N3 C8 1.434(3) . ?
C7 C8 1.364(3) . ?
C9 C10 1.497(3) . ?
C10 C11 1.523(3) . ?
C4 C3 1.508(5) . ?
C3 O1 1.253(7) 3_667 ?

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
O3 Cu1 O2 167.56(8) . . ?
O3 Cu1 O1 91.41(8) . . ?
O2 Cu1 O1 88.73(9) . . ?
O3 Cu1 O4 86.90(6) . . ?
O2 Cu1 O4 90.36(6) . . ?
O1 Cu1 O4 167.90(10) . . ?
O3 Cu1 N1 98.34(7) . . ?
O2 Cu1 N1 94.08(7) . . ?
O1 Cu1 N1 93.40(10) . . ?
O4 Cu1 N1 98.70(8) . . ?
O3 Cu1 Cu1 83.90(6) . 3_667 ?
O2 Cu1 Cu1 83.80(6) . 3_667 ?
O1 Cu1 Cu1 81.71(8) . 3_667 ?
O4 Cu1 Cu1 86.20(6) . 3_667 ?
N1 Cu1 Cu1 174.69(6) . 3_667 ?
C3 O4 Cu1 120.6(3) . . ?
C3 O1 Cu1 126.32(18) 3_667 . ?
O2 C1 O3 125.08(17) . 3_667 ?
O2 C1 C2 117.7(2) . . ?
O3 C1 C2 117.2(3) 3_667 . ?
C1 O2 Cu1 123.43(13) . . ?
C1 O3 Cu1 123.59(16) 3_667 . ?
C6 N2 C8 105.47(16) . . ?
C6 N2 C9 124.25(19) . . ?
C8 N2 C9 129.69(18) . . ?
C6 N1 C7 106.73(18) . . ?
C6 N1 Cu1 129.04(19) . . ?
C7 N1 Cu1 119.97(15) . . ?
O5 N3 O6 123.2(3) . . ?
O5 N3 C8 119.2(2) . . ?
O6 N3 C8 117.4(2) . . ?
N1 C7 C8 108.16(17) . . ?
N2 C9 C10 110.9(2) . . ?
O7 C10 C9 109.5(2) . . ?
O7 C10 C11 108.28(19) . . ?
C9 C10 C11 112.0(2) . . ?
N1 C6 N2 111.45(18) . . ?
N1 C6 C5 123.7(2) . . ?
N2 C6 C5 124.84(18) . . ?
C10 C11 Cl1 112.09(16) . . ?
C7 C8 N2 108.2(2) . . ?
C7 C8 N3 125.56(19) . . ?
N2 C8 N3 126.2(2) . . ?
O1 C3 O4 124.9(4) 3_667 . ?
O1 C3 C4 118.4(3) 3_667 . ?
O4 C3 C4 116.6(5) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.025
