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

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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.
#
#  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
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  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.
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data_added_by_encifer


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C H18 Cu2 N6 O3, 2(Cl O4)'
_chemical_formula_sum            'C0.25 H4.50 Cl0.50 Cu0.50 N1.50 O2.75'
_chemical_formula_weight         122.05

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           orthorhombic
_symmetry_space_group_name_H-M   'P b a m'
_symmetry_space_group_name_Hall  '-P 2 2ab'

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

_cell_length_a                   9.277(3)
_cell_length_b                   17.304(6)
_cell_length_c                   4.7930(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     769.4(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1520
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      26.19

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.107
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             492
_exptl_absorpt_coefficient_mu    3.175
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2790
_exptl_absorpt_correction_T_max  0.7632
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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 APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_number         0
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            3566
_diffrn_reflns_av_R_equivalents  0.0969
_diffrn_reflns_av_sigmaI/netI    0.0812
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         26.27
_reflns_number_total             875
_reflns_number_gt                783
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_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)+(0.0572P)²+8.2000P] 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         875
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.1539
_refine_ls_wR_factor_gt          0.1509
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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 0.38255(9) -0.08358(5) 1.0000 0.0120(4) Uani 1 2 d S . .
Cl1 Cl -0.0823(3) -0.15413(16) 0.5777(5) 0.0174(8) Uani 0.50 1 d P . .
N1 N 0.5558(7) -0.1540(4) 1.0000 0.0276(19) Uani 1 2 d S . .
H1 H 0.5316 -0.2001 0.9222 0.041 Uiso 0.50 1 calc PR . .
H2 H 0.5860 -0.1616 1.1785 0.041 Uiso 0.50 1 calc PR . .
H3 H 0.6280 -0.1319 0.8992 0.041 Uiso 0.50 1 calc PR . .
O1 O -0.0670(11) -0.1588(6) 0.875(2) 0.033(2) Uani 0.50 1 d P . .
O5 O 0.5000 0.0000 0.822(2) 0.011(2) Uani 0.50 2 d SP . .
N2 N 0.2024(8) -0.0179(5) 1.0000 0.040(2) Uani 1 2 d S . .
H4 H 0.1285 -0.0449 0.9221 0.059 Uiso 0.50 1 calc PR . .
H5 H 0.2184 0.0259 0.8993 0.059 Uiso 0.50 1 calc PR . .
H6 H 0.1792 -0.0050 1.1785 0.059 Uiso 0.50 1 calc PR . .
C1 C 0.5000 0.0000 0.5000 0.026(3) Uani 1 4 d S . .
O2 O -0.2217(8) -0.1263(7) 0.5000 0.067(3) Uani 1 2 d S . .
N3 N 0.2590(9) -0.1764(5) 0.906(2) 0.023(3) Uani 0.50 1 d P . .
H7 H 0.2424 -0.1776 0.7185 0.035 Uiso 0.50 1 calc PR . .
H8 H 0.1735 -0.1731 0.9979 0.035 Uiso 1 2 calc SR . .
H9 H 0.3055 -0.2204 0.9578 0.035 Uiso 0.50 1 calc PR . .
O3 O 0.0186(10) -0.0991(5) 0.5000 0.058(3) Uani 1 2 d S . .
O4 O -0.0528(17) -0.2284(5) 0.5000 0.094(4) Uani 1 2 d S . .
O6 O 0.4244(8) -0.0518(5) 0.5743(15) 0.019(2) Uani 0.50 1 d P . .

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 0.0087(5) 0.0087(5) 0.0185(6) 0.000 0.000 -0.0020(3)
Cl1 0.0146(11) 0.0192(13) 0.018(2) -0.0013(9) -0.0001(9) 0.0001(9)
N1 0.015(3) 0.009(3) 0.059(6) 0.000 0.000 0.001(3)
O1 0.046(6) 0.038(6) 0.016(4) 0.001(4) -0.006(4) 0.004(5)
O5 0.015(5) 0.013(5) 0.004(5) 0.000 0.000 -0.004(4)
N2 0.013(3) 0.016(4) 0.089(8) 0.000 0.000 0.005(3)
C1 0.005(5) 0.009(6) 0.065(10) 0.000 0.000 0.004(4)
O2 0.019(4) 0.137(10) 0.046(5) 0.000 0.000 0.019(5)
N3 0.015(4) 0.008(4) 0.047(8) -0.007(4) -0.001(4) -0.006(3)
O3 0.054(5) 0.055(6) 0.065(6) 0.000 0.000 -0.035(4)
O4 0.172(12) 0.015(4) 0.095(9) 0.000 0.000 0.016(6)
O6 0.021(4) 0.027(4) 0.009(6) 0.003(3) 0.002(3) -0.010(3)

_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 O5 2.001(5) 5_657 ?
Cu1 O5 2.001(5) 2_655 ?
Cu1 O5 2.001(5) . ?
Cu1 N1 2.016(7) . ?
Cu1 N2 2.021(7) . ?
Cu1 N3 2.025(8) . ?
Cu1 N3 2.025(8) 6_557 ?
Cu1 O6 2.149(7) 6_557 ?
Cu1 O6 2.149(7) . ?
Cu1 O6 2.833(7) 6_556 ?
Cl1 O4 1.365(9) . ?
Cl1 O3 1.387(8) . ?
Cl1 O2 1.429(8) . ?
Cl1 O1 1.435(10) . ?
O5 O5 0.00(2) 2_655 ?
O5 C1 1.544(10) . ?
O5 Cu1 2.001(4) 5_657 ?
C1 O6 1.193(7) 5_656 ?
C1 O6 1.193(7) 2_655 ?
C1 O6 1.193(7) 6_556 ?
C1 O6 1.193(7) . ?
C1 O5 1.544(10) 5_656 ?
C1 O5 1.544(10) 2_655 ?
O2 Cl1 1.429(8) 6_556 ?
O3 Cl1 1.387(8) 6_556 ?
O4 Cl1 1.365(9) 6_556 ?
O6 Cu1 2.833(7) 6_556 ?

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
O5 Cu1 O5 50.4(5) 5_657 2_655 ?
O5 Cu1 O5 50.4(5) 5_657 . ?
O5 Cu1 O5 0.0(5) 2_655 . ?
O5 Cu1 N1 90.14(19) 5_657 . ?
O5 Cu1 N1 90.14(19) 2_655 . ?
O5 Cu1 N1 90.14(19) . . ?
O5 Cu1 N2 92.5(2) 5_657 . ?
O5 Cu1 N2 92.5(2) 2_655 . ?
O5 Cu1 N2 92.5(2) . . ?
N1 Cu1 N2 177.1(3) . . ?
O5 Cu1 N3 167.6(4) 5_657 . ?
O5 Cu1 N3 141.8(4) 2_655 . ?
O5 Cu1 N3 141.8(4) . . ?
N1 Cu1 N3 88.4(3) . . ?
N2 Cu1 N3 88.8(3) . . ?
O5 Cu1 N3 141.8(4) 5_657 6_557 ?
O5 Cu1 N3 167.6(4) 2_655 6_557 ?
O5 Cu1 N3 167.6(4) . 6_557 ?
N1 Cu1 N3 88.4(3) . 6_557 ?
N2 Cu1 N3 88.8(3) . 6_557 ?
N3 Cu1 N3 25.8(6) . 6_557 ?
O5 Cu1 O6 46.5(3) 5_657 6_557 ?
O5 Cu1 O6 97.0(3) 2_655 6_557 ?
O5 Cu1 O6 97.0(3) . 6_557 ?
N1 Cu1 O6 90.6(2) . 6_557 ?
N2 Cu1 O6 90.3(2) . 6_557 ?
N3 Cu1 O6 121.2(4) . 6_557 ?
N3 Cu1 O6 95.3(4) 6_557 6_557 ?
O5 Cu1 O6 97.0(3) 5_657 . ?
O5 Cu1 O6 46.5(3) 2_655 . ?
O5 Cu1 O6 46.5(3) . . ?
N1 Cu1 O6 90.6(2) . . ?
N2 Cu1 O6 90.3(2) . . ?
N3 Cu1 O6 95.3(4) . . ?
N3 Cu1 O6 121.2(4) 6_557 . ?
O6 Cu1 O6 143.5(4) 6_557 . ?
O5 Cu1 O6 101.5(3) 5_657 6_556 ?
O5 Cu1 O6 51.1(3) 2_655 6_556 ?
O5 Cu1 O6 51.1(3) . 6_556 ?
N1 Cu1 O6 90.47(18) . 6_556 ?
N2 Cu1 O6 90.23(17) . 6_556 ?
N3 Cu1 O6 90.8(4) . 6_556 ?
N3 Cu1 O6 116.7(4) 6_557 6_556 ?
O6 Cu1 O6 148.0(3) 6_557 6_556 ?
O6 Cu1 O6 4.51(10) . 6_556 ?
O4 Cl1 O3 116.0(7) . . ?
O4 Cl1 O2 115.3(8) . . ?
O3 Cl1 O2 108.0(7) . . ?
O4 Cl1 O1 101.4(5) . . ?
O3 Cl1 O1 103.8(5) . . ?
O2 Cl1 O1 111.5(5) . . ?
O5 O5 C1 0(10) 2_655 . ?
O5 O5 Cu1 0(10) 2_655 . ?
C1 O5 Cu1 115.2(3) . . ?
O5 O5 Cu1 0(10) 2_655 5_657 ?
C1 O5 Cu1 115.2(3) . 5_657 ?
Cu1 O5 Cu1 129.6(5) . 5_657 ?
O6 C1 O6 34.7(7) 5_656 2_655 ?
O6 C1 O6 145.3(7) 5_656 6_556 ?
O6 C1 O6 180.0(7) 2_655 6_556 ?
O6 C1 O6 180.0(5) 5_656 . ?
O6 C1 O6 145.3(7) 2_655 . ?
O6 C1 O6 34.7(7) 6_556 . ?
O6 C1 O5 72.6(3) 5_656 5_656 ?
O6 C1 O5 107.4(3) 2_655 5_656 ?
O6 C1 O5 72.6(3) 6_556 5_656 ?
O6 C1 O5 107.4(3) . 5_656 ?
O6 C1 O5 107.4(3) 5_656 . ?
O6 C1 O5 72.6(3) 2_655 . ?
O6 C1 O5 107.4(3) 6_556 . ?
O6 C1 O5 72.6(3) . . ?
O5 C1 O5 179.998(1) 5_656 . ?
O6 C1 O5 107.4(3) 5_656 2_655 ?
O6 C1 O5 72.6(3) 2_655 2_655 ?
O6 C1 O5 107.4(3) 6_556 2_655 ?
O6 C1 O5 72.6(3) . 2_655 ?
O5 C1 O5 179.998(1) 5_656 2_655 ?
O5 C1 O5 0.000(2) . 2_655 ?
Cl1 O2 Cl1 30.2(3) . 6_556 ?
Cl1 O3 Cl1 31.2(3) 6_556 . ?
Cl1 O4 Cl1 31.7(3) . 6_556 ?
C1 O6 Cu1 125.6(5) . . ?
C1 O6 Cu1 86.4(4) . 6_556 ?
Cu1 O6 Cu1 148.0(3) . 6_556 ?

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
O5 Cu1 O5 O5 0(100) 5_657 . . 2_655 ?
N1 Cu1 O5 O5 0.00(14) . . . 2_655 ?
N2 Cu1 O5 O5 0.00(13) . . . 2_655 ?
N3 Cu1 O5 O5 0.00(15) . . . 2_655 ?
N3 Cu1 O5 O5 0.0(3) 6_557 . . 2_655 ?
O6 Cu1 O5 O5 0.00(14) 6_557 . . 2_655 ?
O6 Cu1 O5 O5 0.00(14) . . . 2_655 ?
O6 Cu1 O5 O5 0.00(14) 6_556 . . 2_655 ?
O5 Cu1 O5 C1 180.0 5_657 . . . ?
O5 Cu1 O5 C1 0(4) 2_655 . . . ?
N1 Cu1 O5 C1 89.93(9) . . . . ?
N2 Cu1 O5 C1 -88.82(10) . . . . ?
N3 Cu1 O5 C1 2.3(4) . . . . ?
N3 Cu1 O5 C1 6.8(12) 6_557 . . . ?
O6 Cu1 O5 C1 -179.4(2) 6_557 . . . ?
O6 Cu1 O5 C1 -0.8(3) . . . . ?
O6 Cu1 O5 C1 -0.6(2) 6_556 . . . ?
O5 Cu1 O5 Cu1 0.0 5_657 . . 5_657 ?
O5 Cu1 O5 Cu1 0(100) 2_655 . . 5_657 ?
N1 Cu1 O5 Cu1 -90.07(9) . . . 5_657 ?
N2 Cu1 O5 Cu1 91.17(10) . . . 5_657 ?
N3 Cu1 O5 Cu1 -177.7(4) . . . 5_657 ?
N3 Cu1 O5 Cu1 -173.2(12) 6_557 . . 5_657 ?
O6 Cu1 O5 Cu1 0.6(2) 6_557 . . 5_657 ?
O6 Cu1 O5 Cu1 179.2(3) . . . 5_657 ?
O6 Cu1 O5 Cu1 179.4(2) 6_556 . . 5_657 ?
O5 O5 C1 O6 0(100) 2_655 . . 5_656 ?
Cu1 O5 C1 O6 -178.9(4) . . . 5_656 ?
Cu1 O5 C1 O6 1.1(4) 5_657 . . 5_656 ?
O5 O5 C1 O6 0(100) 2_655 . . 2_655 ?
Cu1 O5 C1 O6 -178.9(4) . . . 2_655 ?
Cu1 O5 C1 O6 1.1(4) 5_657 . . 2_655 ?
O5 O5 C1 O6 0(25) 2_655 . . 6_556 ?
Cu1 O5 C1 O6 1.1(4) . . . 6_556 ?
Cu1 O5 C1 O6 -178.9(4) 5_657 . . 6_556 ?
O5 O5 C1 O6 0(25) 2_655 . . . ?
Cu1 O5 C1 O6 1.1(4) . . . . ?
Cu1 O5 C1 O6 -178.9(4) 5_657 . . . ?
O5 O5 C1 O5 0(100) 2_655 . . 5_656 ?
Cu1 O5 C1 O5 -41(9) . . . 5_656 ?
Cu1 O5 C1 O5 139(9) 5_657 . . 5_656 ?
Cu1 O5 C1 O5 0(100) . . . 2_655 ?
Cu1 O5 C1 O5 0(34) 5_657 . . 2_655 ?
O4 Cl1 O2 Cl1 -63.9(4) . . . 6_556 ?
O3 Cl1 O2 Cl1 67.6(3) . . . 6_556 ?
O1 Cl1 O2 Cl1 -178.9(5) . . . 6_556 ?
O4 Cl1 O3 Cl1 63.2(5) . . . 6_556 ?
O2 Cl1 O3 Cl1 -68.0(3) . . . 6_556 ?
O1 Cl1 O3 Cl1 173.5(4) . . . 6_556 ?
O3 Cl1 O4 Cl1 -63.3(5) . . . 6_556 ?
O2 Cl1 O4 Cl1 64.3(4) . . . 6_556 ?
O1 Cl1 O4 Cl1 -175.0(4) . . . 6_556 ?
O6 C1 O6 Cu1 -172(6) 5_656 . . . ?
O6 C1 O6 Cu1 -1.1(4) 2_655 . . . ?
O6 C1 O6 Cu1 178.9(4) 6_556 . . . ?
O5 C1 O6 Cu1 178.9(4) 5_656 . . . ?
O5 C1 O6 Cu1 -1.1(4) . . . . ?
O5 C1 O6 Cu1 -1.1(4) 2_655 . . . ?
O6 C1 O6 Cu1 9(6) 5_656 . . 6_556 ?
O6 C1 O6 Cu1 -179.3(3) 2_655 . . 6_556 ?
O6 C1 O6 Cu1 0.7(3) 6_556 . . 6_556 ?
O5 C1 O6 Cu1 0.7(3) 5_656 . . 6_556 ?
O5 C1 O6 Cu1 -179.3(3) . . . 6_556 ?
O5 C1 O6 Cu1 -179.3(3) 2_655 . . 6_556 ?
O5 Cu1 O6 C1 1.7(7) 5_657 . . . ?
O5 Cu1 O6 C1 1.1(4) 2_655 . . . ?
O5 Cu1 O6 C1 1.1(4) . . . . ?
N1 Cu1 O6 C1 -88.5(7) . . . . ?
N2 Cu1 O6 C1 94.3(7) . . . . ?
N3 Cu1 O6 C1 -176.9(7) . . . . ?
N3 Cu1 O6 C1 -177.0(6) 6_557 . . . ?
O6 Cu1 O6 C1 3.4(13) 6_557 . . . ?
O6 Cu1 O6 C1 -176.6(13) 6_556 . . . ?
O5 Cu1 O6 Cu1 178.4(6) 5_657 . . 6_556 ?
O5 Cu1 O6 Cu1 177.7(9) 2_655 . . 6_556 ?
O5 Cu1 O6 Cu1 177.7(9) . . . 6_556 ?
N1 Cu1 O6 Cu1 88.1(7) . . . 6_556 ?
N2 Cu1 O6 Cu1 -89.1(7) . . . 6_556 ?
N3 Cu1 O6 Cu1 -0.3(7) . . . 6_556 ?
N3 Cu1 O6 Cu1 -0.4(9) 6_557 . . 6_556 ?
O6 Cu1 O6 Cu1 180.002(1) 6_557 . . 6_556 ?
O6 Cu1 O6 Cu1 0.000(14) 6_556 . . 6_556 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.27
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.213
_refine_diff_density_min         -1.045
_refine_diff_density_rms         0.206
_database_code_depnum_ccdc_archive 'CCDC 1003017'
#######################################################################
#
#                 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_added_by_encifer


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C H17 Cu2 N5 O4, 2(Cl O4)'
_chemical_formula_sum            'C0.50 H8.50 Cl Cu N2.50 O6'
_chemical_formula_weight         244.59

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           ?
_symmetry_space_group_name_H-M   'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'

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

_cell_length_a                   9.8063(6)
_cell_length_b                   15.1247(9)
_cell_length_c                   9.8609(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1462.54(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4733
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      25.35

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    3.344
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5266
_exptl_absorpt_correction_T_max  0.6339
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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 APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_number         0
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            9632
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         25.34
_reflns_number_total             1384
_reflns_number_gt                1149
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_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+3.6139P] 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         1384
_refine_ls_number_parameters     143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0713
_refine_ls_wR_factor_gt          0.0672
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_restrained_S_all      1.164
_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 -0.02401(5) 0.7500 0.06021(5) 0.01077(16) Uani 1 2 d S . .
Cu2 Cu 0.02424(5) 0.7500 0.43405(5) 0.01016(16) Uani 1 2 d S . .
N1 N 0.0256(3) 0.61863(19) 0.4465(3) 0.0203(6) Uani 1 1 d . . .
H1 H 0.0935 0.5967 0.3934 0.031 Uiso 1 1 calc R . .
H2 H -0.0560 0.5970 0.4178 0.031 Uiso 1 1 calc R . .
H3 H 0.0399 0.6021 0.5341 0.031 Uiso 1 1 calc R . .
N2 N -0.0210(3) 0.61743(18) 0.0620(3) 0.0153(6) Uani 1 1 d . . .
H4 H 0.0657 0.5983 0.0765 0.023 Uiso 1 1 calc R . .
H5 H -0.0513 0.5966 -0.0192 0.023 Uiso 1 1 calc R . .
H6 H -0.0761 0.5972 0.1295 0.023 Uiso 1 1 calc R . .
N3 N 0.0133(4) 0.7500 -0.1427(4) 0.0184(9) Uani 1 2 d S . .
H7 H 0.0246 0.6934 -0.1719 0.028 Uiso 0.50 1 calc PR . .
H8 H 0.0903 0.7816 -0.1600 0.028 Uiso 0.50 1 calc PR . .
H9 H -0.0584 0.7750 -0.1870 0.028 Uiso 0.50 1 calc PR . .
C1 C 0.2658(4) 0.7500 0.2604(4) 0.0101(9) Uani 1 2 d S . .
O1 O 0.2153(3) 0.7500 0.3809(3) 0.0152(7) Uani 1 2 d S . .
O2 O 0.1934(3) 0.7500 0.1540(3) 0.0171(7) Uani 1 2 d S . .
O3 O -0.1028(3) 0.7500 0.2476(3) 0.0102(6) Uani 1 2 d S . .
Cl1 Cl 0.2738(3) 0.5500(2) 0.7611(4) 0.0141(7) Uani 0.522(5) 1 d P A 1
Cl2 Cl 0.2205(4) 0.5460(3) 0.7564(4) 0.0142(7) Uani 0.478(5) 1 d P A 2
O4 O 0.2416(3) 0.46105(17) 0.7160(3) 0.0335(6) Uani 1 1 d . . .
O5 O 0.2476(3) 0.56121(18) 0.8980(2) 0.0326(6) Uani 1 1 d . . .
O6 O -0.1483(3) 0.7500 0.5525(3) 0.0200(7) Uani 1 2 d S . .
O7 O 0.2200(7) 0.6221(5) 0.6845(7) 0.0294(16) Uani 0.522(5) 1 d P A 1
O8 O 0.4213(4) 0.5541(3) 0.7523(4) 0.0218(13) Uani 0.522(5) 1 d P A 1
O9 O 0.2823(7) 0.6068(6) 0.6641(8) 0.0283(18) Uani 0.478(5) 1 d P A 2
O10 O 0.0747(5) 0.5556(3) 0.7474(5) 0.0203(14) Uani 0.478(5) 1 d P A 2

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 0.0097(3) 0.0128(3) 0.0098(3) 0.000 0.0008(2) 0.000
Cu2 0.0073(3) 0.0124(3) 0.0108(3) 0.000 0.0008(2) 0.000
N1 0.0211(15) 0.0169(16) 0.0231(15) 0.0023(12) -0.0068(12) -0.0043(13)
N2 0.0160(14) 0.0157(15) 0.0141(13) 0.0000(11) 0.0008(11) -0.0010(12)
N3 0.025(2) 0.016(2) 0.0140(19) 0.000 0.0009(16) 0.000
C1 0.006(2) 0.008(2) 0.017(2) 0.000 -0.0001(18) 0.000
O1 0.0069(14) 0.0253(18) 0.0134(16) 0.000 0.0020(12) 0.000
O2 0.0066(14) 0.0301(19) 0.0148(16) 0.000 -0.0054(13) 0.000
O3 0.0041(13) 0.0159(16) 0.0105(14) 0.000 -0.0010(12) 0.000
Cl1 0.0132(16) 0.0129(11) 0.0161(10) 0.0021(8) 0.0009(14) -0.0001(14)
Cl2 0.0135(17) 0.0141(12) 0.0148(10) 0.0009(8) -0.0009(16) -0.0007(15)
O4 0.0413(15) 0.0238(14) 0.0354(15) -0.0123(12) 0.0127(13) -0.0113(13)
O5 0.0453(16) 0.0336(15) 0.0187(12) -0.0063(11) -0.0044(12) 0.0013(14)
O6 0.0104(15) 0.033(2) 0.0168(17) 0.000 0.0033(13) 0.000
O7 0.025(4) 0.026(4) 0.037(4) 0.014(3) -0.005(3) 0.003(3)
O8 0.010(2) 0.031(3) 0.024(2) 0.001(2) 0.0020(19) -0.0007(19)
O9 0.019(4) 0.029(4) 0.036(4) 0.011(3) 0.008(3) 0.000(3)
O10 0.010(2) 0.022(3) 0.029(3) 0.002(2) 0.000(2) 0.000(2)

_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 2.003(3) . ?
Cu1 N2 2.005(3) 8_575 ?
Cu1 N2 2.005(3) . ?
Cu1 N3 2.034(4) . ?
Cu1 O2 2.324(3) . ?
Cu2 O1 1.946(3) . ?
Cu2 N1 1.991(3) . ?
Cu2 N1 1.991(3) 8_575 ?
Cu2 O6 2.056(3) . ?
Cu2 O3 2.221(3) . ?
C1 O2 1.267(5) . ?
C1 O1 1.287(5) . ?
C1 O3 1.291(5) 6_656 ?
O3 C1 1.291(5) 6_556 ?
Cl1 O5 1.384(5) . ?
Cl1 O7 1.428(8) . ?
Cl1 O8 1.451(5) . ?
Cl1 O4 1.452(4) . ?
Cl2 O4 1.361(5) . ?
Cl2 O9 1.429(9) . ?
Cl2 O5 1.440(5) . ?
Cl2 O10 1.441(6) . ?

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 N2 89.86(7) . 8_575 ?
O3 Cu1 N2 89.86(7) . . ?
N2 Cu1 N2 178.05(15) 8_575 . ?
O3 Cu1 N3 167.65(14) . . ?
N2 Cu1 N3 90.34(7) 8_575 . ?
N2 Cu1 N3 90.34(7) . . ?
O3 Cu1 O2 89.24(11) . . ?
N2 Cu1 O2 89.03(8) 8_575 . ?
N2 Cu1 O2 89.03(8) . . ?
N3 Cu1 O2 103.11(13) . . ?
O1 Cu2 N1 90.59(8) . . ?
O1 Cu2 N1 90.59(8) . 8_575 ?
N1 Cu2 N1 172.86(16) . 8_575 ?
O1 Cu2 O6 161.03(13) . . ?
N1 Cu2 O6 88.30(8) . . ?
N1 Cu2 O6 88.30(8) 8_575 . ?
O1 Cu2 O3 108.48(11) . . ?
N1 Cu2 O3 93.15(8) . . ?
N1 Cu2 O3 93.15(8) 8_575 . ?
O6 Cu2 O3 90.49(11) . . ?
O2 C1 O1 123.3(4) . . ?
O2 C1 O3 120.6(4) . 6_656 ?
O1 C1 O3 116.1(4) . 6_656 ?
C1 O1 Cu2 128.3(3) . . ?
C1 O2 Cu1 147.6(3) . . ?
C1 O3 Cu1 109.2(2) 6_556 . ?
C1 O3 Cu2 127.6(3) 6_556 . ?
Cu1 O3 Cu2 123.18(13) . . ?
O5 Cl1 O7 110.8(4) . . ?
O5 Cl1 O8 103.8(3) . . ?
O7 Cl1 O8 107.7(4) . . ?
O5 Cl1 O4 111.8(3) . . ?
O7 Cl1 O4 117.7(4) . . ?
O8 Cl1 O4 103.7(3) . . ?
O4 Cl2 O9 110.9(5) . . ?
O4 Cl2 O5 114.0(3) . . ?
O9 Cl2 O5 115.9(4) . . ?
O4 Cl2 O10 103.1(3) . . ?
O9 Cl2 O10 108.5(5) . . ?
O5 Cl2 O10 103.1(3) . . ?
Cl2 O4 Cl1 21.32(12) . . ?
Cl1 O5 Cl2 21.44(11) . . ?

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 C1 O1 Cu2 0.000(1) . . . . ?
O3 C1 O1 Cu2 180.0 6_656 . . . ?
N1 Cu2 O1 C1 93.52(8) . . . . ?
N1 Cu2 O1 C1 -93.52(8) 8_575 . . . ?
O6 Cu2 O1 C1 180.000(2) . . . . ?
O3 Cu2 O1 C1 0.000(1) . . . . ?
O1 C1 O2 Cu1 0.0 . . . . ?
O3 C1 O2 Cu1 180.0 6_656 . . . ?
O3 Cu1 O2 C1 0.0 . . . . ?
N2 Cu1 O2 C1 89.87(7) 8_575 . . . ?
N2 Cu1 O2 C1 -89.88(7) . . . . ?
N3 Cu1 O2 C1 180.0 . . . . ?
N2 Cu1 O3 C1 90.97(8) 8_575 . . 6_556 ?
N2 Cu1 O3 C1 -90.97(8) . . . 6_556 ?
N3 Cu1 O3 C1 0.0 . . . 6_556 ?
O2 Cu1 O3 C1 180.0 . . . 6_556 ?
N2 Cu1 O3 Cu2 -89.03(8) 8_575 . . . ?
N2 Cu1 O3 Cu2 89.03(8) . . . . ?
N3 Cu1 O3 Cu2 180.0 . . . . ?
O2 Cu1 O3 Cu2 0.0 . . . . ?
O1 Cu2 O3 C1 180.0 . . . 6_556 ?
N1 Cu2 O3 C1 88.32(8) . . . 6_556 ?
N1 Cu2 O3 C1 -88.32(8) 8_575 . . 6_556 ?
O6 Cu2 O3 C1 -0.002(1) . . . 6_556 ?
O1 Cu2 O3 Cu1 0.0 . . . . ?
N1 Cu2 O3 Cu1 -91.68(8) . . . . ?
N1 Cu2 O3 Cu1 91.68(8) 8_575 . . . ?
O6 Cu2 O3 Cu1 180.0 . . . . ?
O9 Cl2 O4 Cl1 61.6(8) . . . . ?
O5 Cl2 O4 Cl1 -71.3(8) . . . . ?
O10 Cl2 O4 Cl1 177.6(11) . . . . ?
O5 Cl1 O4 Cl2 75.8(8) . . . . ?
O7 Cl1 O4 Cl2 -54.1(8) . . . . ?
O8 Cl1 O4 Cl2 -173.0(10) . . . . ?
O7 Cl1 O5 Cl2 67.7(8) . . . . ?
O8 Cl1 O5 Cl2 -176.9(10) . . . . ?
O4 Cl1 O5 Cl2 -65.7(8) . . . . ?
O4 Cl2 O5 Cl1 81.3(8) . . . . ?
O9 Cl2 O5 Cl1 -49.2(8) . . . . ?
O10 Cl2 O5 Cl1 -167.6(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.087
_database_code_depnum_ccdc_archive 'CCDC 1003018'
