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

#######################################################################
#
#                 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H30 Cu2 N6 O10, 0.5(O h2)'
_chemical_formula_sum            'C26 H31 Cu2 N6 O10.50'
_chemical_formula_weight         722.65

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           Orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'

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

_cell_length_a                   12.5992(6)
_cell_length_b                   7.8436(4)
_cell_length_c                   30.4801(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3012.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9980
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      25.31

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1484
_exptl_absorpt_coefficient_mu    1.479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5892
_exptl_absorpt_correction_T_max  0.8909
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            37222
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         25.40
_reflns_number_total             2761
_reflns_number_gt                2220
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.0345P)²+3.8019P] 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         2761
_refine_ls_number_parameters     215
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0772
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.088
_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 0.99454(2) 0.16513(4) 0.352018(10) 0.02599(12) Uani 1 1 d . . .
O1 O 0.86189(16) 0.0684(3) 0.23315(7) 0.0395(5) Uani 1 1 d . . .
O2 O 0.94078(14) 0.2834(2) 0.19752(6) 0.0284(4) Uani 1 1 d . . .
O3 O 1.11943(15) 0.2036(3) 0.38857(6) 0.0339(5) Uani 1 1 d . A .
O4 O 1.0167(4) 0.4247(8) 0.4065(4) 0.0483(16) Uani 0.78(2) 1 d P A 1
O4A O 1.0256(16) 0.393(3) 0.4237(10) 0.0483(16) Uani 0.22(2) 1 d P A 2
O5 O 1.04357(16) -0.1141(3) 0.32644(7) 0.0383(5) Uani 1 1 d D . .
H5A H 1.074(2) -0.061(4) 0.3049(7) 0.046 Uiso 1 1 d D . .
O6 O 0.9563(19) 0.419(3) 0.4988(8) 0.052(4) Uiso 0.13 1 d P . 1
O6A O 0.942(2) 0.370(3) 0.5032(8) 0.052(4) Uiso 0.13 1 d P B 2
N1 N 0.79058(16) 0.2730(3) 0.29769(7) 0.0258(5) Uani 1 1 d . . .
N2 N 0.84388(17) 0.1930(3) 0.33005(7) 0.0247(5) Uani 1 1 d . . .
N3 N 0.91472(18) 0.0430(3) 0.40019(7) 0.0297(5) Uani 1 1 d . . .
C1 C 0.6852(2) 0.2585(4) 0.30391(9) 0.0308(7) Uani 1 1 d . . .
H1 H 0.6327 0.3034 0.2858 0.037 Uiso 1 1 calc R . .
C2 C 0.6685(2) 0.1663(4) 0.34146(9) 0.0300(6) Uani 1 1 d . . .
H2 H 0.6039 0.1357 0.3539 0.036 Uiso 1 1 calc R . .
C3 C 0.7696(2) 0.1286(3) 0.35670(8) 0.0259(6) Uani 1 1 d . . .
C4 C 0.8082(2) 0.0399(3) 0.39565(8) 0.0274(6) Uani 1 1 d . . .
C5 C 0.7433(2) -0.0433(4) 0.42564(9) 0.0334(7) Uani 1 1 d . . .
H5 H 0.6699 -0.0436 0.4222 0.040 Uiso 1 1 calc R . .
C6 C 0.7899(3) -0.1253(4) 0.46055(10) 0.0401(8) Uani 1 1 d . . .
H6 H 0.7481 -0.1816 0.4811 0.048 Uiso 1 1 calc R . .
C7 C 0.8985(3) -0.1238(4) 0.46493(10) 0.0437(8) Uani 1 1 d . . .
H7 H 0.9310 -0.1799 0.4882 0.052 Uiso 1 1 calc R . .
C8 C 0.9585(3) -0.0377(4) 0.43419(10) 0.0400(7) Uani 1 1 d . . .
H8 H 1.0319 -0.0359 0.4373 0.048 Uiso 1 1 calc R . .
C9 C 0.8442(2) 0.3506(3) 0.26070(8) 0.0262(6) Uani 1 1 d . . .
H9A H 0.9036 0.4176 0.2713 0.031 Uiso 1 1 calc R . .
H9B H 0.7956 0.4274 0.2459 0.031 Uiso 1 1 calc R . .
C10 C 0.88470(19) 0.2195(4) 0.22797(8) 0.0247(6) Uani 1 1 d . . .
C11 C 1.1033(3) 0.3409(4) 0.41000(10) 0.0399(8) Uani 1 1 d . . .
C12 C 1.1968(3) 0.4072(5) 0.43601(12) 0.0659(12) Uani 1 1 d . A .
H12A H 1.2331 0.4929 0.4193 0.099 Uiso 1 1 calc R . .
H12B H 1.2446 0.3150 0.4422 0.099 Uiso 1 1 calc R . .
H12C H 1.1721 0.4558 0.4631 0.099 Uiso 1 1 calc R . .
C13 C 1.1176(3) -0.2281(6) 0.34524(13) 0.0636(11) Uani 1 1 d . . .
H13A H 1.1841 -0.1707 0.3495 0.095 Uiso 1 1 calc R . .
H13B H 1.1277 -0.3237 0.3260 0.095 Uiso 1 1 calc R . .
H13C H 1.0914 -0.2675 0.3730 0.095 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 O2 1.9507(18) 3_755 ?
Cu1 O3 1.9515(19) . ?
Cu1 N3 2.021(2) . ?
Cu1 N2 2.025(2) . ?
Cu1 O5 2.405(2) . ?
O1 C10 1.229(3) . ?
O2 C10 1.270(3) . ?
O2 Cu1 1.9507(18) 3_755 ?
O3 C11 1.275(4) . ?
O4 C11 1.278(8) . ?
O4A C11 1.14(2) . ?
O5 C13 1.414(4) . ?
O5 H5A 0.864(10) . ?
O6 O6 1.69(5) 5_766 ?
N1 C1 1.346(3) . ?
N1 N2 1.349(3) . ?
N1 C9 1.449(3) . ?
N2 C3 1.338(3) . ?
N3 C8 1.334(4) . ?
N3 C4 1.350(3) . ?
C1 C2 1.371(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.387(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.459(4) . ?
C4 C5 1.389(4) . ?
C5 C6 1.375(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.381(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.521(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C12 1.513(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
O2 Cu1 O3 91.80(8) 3_755 . ?
O2 Cu1 N3 174.67(8) 3_755 . ?
O3 Cu1 N3 93.43(9) . . ?
O2 Cu1 N2 94.84(8) 3_755 . ?
O3 Cu1 N2 158.14(9) . . ?
N3 Cu1 N2 79.91(9) . . ?
O2 Cu1 O5 94.30(7) 3_755 . ?
O3 Cu1 O5 96.83(8) . . ?
N3 Cu1 O5 86.08(8) . . ?
N2 Cu1 O5 103.40(8) . . ?
C10 O2 Cu1 127.61(17) . 3_755 ?
C11 O3 Cu1 107.12(19) . . ?
C13 O5 Cu1 127.9(2) . . ?
C13 O5 H5A 109(2) . . ?
Cu1 O5 H5A 86(2) . . ?
C1 N1 N2 110.4(2) . . ?
C1 N1 C9 127.3(2) . . ?
N2 N1 C9 122.2(2) . . ?
C3 N2 N1 105.7(2) . . ?
C3 N2 Cu1 114.49(17) . . ?
N1 N2 Cu1 139.37(17) . . ?
C8 N3 C4 118.8(2) . . ?
C8 N3 Cu1 125.7(2) . . ?
C4 N3 Cu1 115.40(18) . . ?
N1 C1 C2 108.3(2) . . ?
N1 C1 H1 125.9 . . ?
C2 C1 H1 125.9 . . ?
C1 C2 C3 104.5(2) . . ?
C1 C2 H2 127.7 . . ?
C3 C2 H2 127.7 . . ?
N2 C3 C2 111.0(2) . . ?
N2 C3 C4 116.1(2) . . ?
C2 C3 C4 132.8(3) . . ?
N3 C4 C5 121.7(3) . . ?
N3 C4 C3 114.0(2) . . ?
C5 C4 C3 124.3(3) . . ?
C6 C5 C4 118.5(3) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C7 C6 C5 119.7(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 118.9(3) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
N3 C8 C7 122.2(3) . . ?
N3 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
N1 C9 C10 112.5(2) . . ?
N1 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
O1 C10 O2 127.2(2) . . ?
O1 C10 C9 119.3(2) . . ?
O2 C10 C9 113.5(2) . . ?
O4A C11 O3 129.0(10) . . ?
O4A C11 O4 27.5(12) . . ?
O3 C11 O4 121.8(4) . . ?
O4A C11 C12 110.7(12) . . ?
O3 C11 C12 115.8(3) . . ?
O4 C11 C12 122.2(4) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C13 H13A 109.5 . . ?
O5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.40
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.063
_database_code_depnum_ccdc_archive 'CCDC 1021990'
#######################################################################
#
#                 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_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H44 Cu2 N10 O18'
_chemical_formula_sum            'C31 H44 Cu2 N10 O18'
_chemical_formula_weight         971.84

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           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.9883(4)
_cell_length_b                   12.4084(5)
_cell_length_c                   16.1803(6)
_cell_angle_alpha                75.070(2)
_cell_angle_beta                 85.468(2)
_cell_angle_gamma                72.003(2)
_cell_volume                     2027.37(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5833
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25.74

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1004
_exptl_absorpt_coefficient_mu    1.137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6002
_exptl_absorpt_correction_T_max  0.9559
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24423
_diffrn_reflns_av_R_equivalents  0.1058
_diffrn_reflns_av_sigmaI/netI    0.1127
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         25.50
_reflns_number_total             7548
_reflns_number_gt                5247
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.0210P)²+11.8511P] 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         7548
_refine_ls_number_parameters     572
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.1691
_refine_ls_wR_factor_gt          0.1589
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.138
_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 0.79548(7) 0.30931(7) 0.94637(5) 0.0134(2) Uani 1 1 d . . .
Cu2 Cu 0.36026(7) 0.36194(7) 0.69500(5) 0.0137(2) Uani 1 1 d . . .
O1 O 0.4418(4) 0.2771(4) 0.8062(3) 0.0171(10) Uani 1 1 d . . .
O2 O 0.6195(4) 0.2236(4) 0.7343(3) 0.0232(11) Uani 1 1 d D . .
O3 O 0.1282(5) 0.5434(4) 0.8768(3) 0.0292(12) Uani 1 1 d . . .
O4 O 0.1065(5) 0.7311(4) 0.8091(3) 0.0297(12) Uani 1 1 d . . .
O5 O 0.6143(4) 0.3783(4) 0.9147(3) 0.0154(10) Uani 1 1 d . . .
O6 O 0.6540(4) 0.4965(5) 0.7935(3) 0.0298(12) Uani 1 1 d . . .
O7 O 0.7590(5) 0.2215(5) 1.0812(3) 0.0255(11) Uani 1 1 d D . .
H7A H 0.700(5) 0.196(6) 1.109(4) 0.031 Uiso 1 1 d D . .
H7B H 0.789(7) 0.244(6) 1.119(3) 0.031 Uiso 1 1 d D . .
O8 O 0.7955(4) 0.4527(4) 0.9756(3) 0.0198(10) Uani 1 1 d D . .
H8A H 0.814(6) 0.438(6) 1.0288(13) 0.024 Uiso 1 1 d D . .
H8B H 0.721(3) 0.504(4) 0.968(4) 0.024 Uiso 1 1 d D . .
O9 O 0.6082(5) 0.9088(5) 0.8095(4) 0.0396(14) Uani 1 1 d . . .
O10 O 0.4696(5) 0.8135(4) 0.8337(3) 0.0322(13) Uani 1 1 d . . .
O11 O 0.4658(6) 0.9370(5) 0.9059(4) 0.0504(16) Uani 1 1 d . . .
O12 O 0.5764(5) 0.6228(4) 0.9648(3) 0.0267(11) Uani 1 1 d D . .
H12A H 0.516(5) 0.633(6) 1.002(4) 0.032 Uiso 1 1 d D . .
H12B H 0.539(6) 0.686(4) 0.928(4) 0.032 Uiso 1 1 d D . .
O13 O 0.7065(6) 0.7267(5) 0.7190(4) 0.0522(17) Uani 1 1 d D . .
H13A H 0.691(8) 0.778(6) 0.748(5) 0.063 Uiso 1 1 d D . .
H13B H 0.660(7) 0.682(6) 0.743(5) 0.063 Uiso 1 1 d D . .
O14 O 1.0253(6) 0.9057(5) 0.6661(4) 0.0480(16) Uani 1 1 d D . .
H14A H 0.989(8) 0.882(8) 0.632(5) 0.058 Uiso 1 1 d D . .
H14B H 0.956(5) 0.959(6) 0.673(6) 0.058 Uiso 1 1 d D . .
O15 O 0.0314(11) 0.7994(12) 0.5235(8) 0.042(3) Uiso 0.50 1 d P A 1
O18 O 0.7949(10) 0.0814(9) 0.6311(6) 0.034(3) Uiso 0.50 1 d PD B 1
O19 O 0.0060(10) 0.6284(10) 0.5154(7) 0.039(2) Uiso 0.50 1 d P C 1
O15A O 0.0268(12) 0.8615(12) 0.5074(8) 0.050(3) Uiso 0.50 1 d P D 2
O18A O 0.8407(10) 0.1156(10) 0.6382(7) 0.043(3) Uiso 0.50 1 d PD E 2
O19A O 0.0026(10) 0.5523(10) 0.5073(7) 0.039(2) Uiso 0.50 1 d P . 2
N1 N 0.8238(5) 0.1637(4) 0.9059(3) 0.0131(11) Uani 1 1 d . . .
N2 N 0.7551(5) 0.1025(5) 0.8843(3) 0.0152(12) Uani 1 1 d . . .
N3 N 0.9885(5) 0.2514(4) 0.9490(3) 0.0143(12) Uani 1 1 d . . .
N4 N 0.1486(5) 0.4137(5) 0.7180(3) 0.0181(12) Uani 1 1 d . . .
N5 N 0.0458(5) 0.4976(5) 0.7359(3) 0.0167(12) Uani 1 1 d . . .
N6 N 0.3171(5) 0.2194(4) 0.6870(3) 0.0176(12) Uani 1 1 d . . .
N7 N 0.3868(5) 0.5154(4) 0.6914(3) 0.0131(11) Uani 1 1 d . . .
N8 N 0.4002(5) 0.5746(5) 0.7480(3) 0.0172(12) Uani 1 1 d . . .
N9 N 0.3428(5) 0.4363(4) 0.5660(3) 0.0147(12) Uani 1 1 d . . .
N10 N 0.5154(6) 0.8870(5) 0.8494(4) 0.0252(14) Uani 1 1 d . . .
C1 C 0.8329(6) 0.0060(5) 0.8620(4) 0.0163(14) Uani 1 1 d . . .
H1 H 0.8071 -0.0488 0.8438 0.020 Uiso 1 1 calc R . .
C2 C 0.9566(6) 0.0040(5) 0.8712(4) 0.0161(14) Uani 1 1 d . . .
H2 H 1.0310 -0.0519 0.8609 0.019 Uiso 1 1 calc R . .
C3 C 0.9471(6) 0.1028(5) 0.8992(4) 0.0151(14) Uani 1 1 d . . .
C4 C 1.0421(6) 0.1495(5) 0.9223(4) 0.0137(14) Uani 1 1 d . . .
C5 C 1.1719(6) 0.1005(6) 0.9192(4) 0.0181(15) Uani 1 1 d . . .
H5 H 1.2059 0.0315 0.9016 0.022 Uiso 1 1 calc R . .
C6 C 1.2514(6) 0.1547(6) 0.9423(4) 0.0239(16) Uani 1 1 d . . .
H6 H 1.3397 0.1219 0.9410 0.029 Uiso 1 1 calc R . .
C7 C 1.1999(6) 0.2577(6) 0.9673(5) 0.0265(17) Uani 1 1 d . . .
H7 H 1.2522 0.2962 0.9820 0.032 Uiso 1 1 calc R . .
C8 C 1.0674(6) 0.3022(6) 0.9700(4) 0.0225(16) Uani 1 1 d . . .
H8 H 1.0323 0.3712 0.9874 0.027 Uiso 1 1 calc R . .
C9 C 0.6159(5) 0.1412(5) 0.8858(4) 0.0132(13) Uani 1 1 d . . .
H9A H 0.5872 0.1833 0.9301 0.016 Uiso 1 1 calc R . .
H9B H 0.5850 0.0734 0.9001 0.016 Uiso 1 1 calc R . .
C10 C 0.5588(6) 0.2200(5) 0.8004(4) 0.0141(14) Uani 1 1 d . . .
C11 C -0.0592(6) 0.4618(6) 0.7471(4) 0.0237(16) Uani 1 1 d . . .
H11 H -0.1404 0.5046 0.7608 0.028 Uiso 1 1 calc R . .
C12 C -0.0263(6) 0.3529(6) 0.7351(4) 0.0230(16) Uani 1 1 d . . .
H12 H -0.0792 0.3062 0.7381 0.028 Uiso 1 1 calc R . .
C13 C 0.1044(6) 0.3255(6) 0.7174(4) 0.0174(14) Uani 1 1 d . . .
C14 C 0.1943(7) 0.2198(6) 0.6982(4) 0.0197(15) Uani 1 1 d . . .
C15 C 0.1575(7) 0.1237(6) 0.6929(4) 0.0277(17) Uani 1 1 d . . .
H15 H 0.0725 0.1247 0.7013 0.033 Uiso 1 1 calc R . .
C16 C 0.2479(8) 0.0274(6) 0.6752(5) 0.0305(18) Uani 1 1 d . . .
H16 H 0.2245 -0.0364 0.6699 0.037 Uiso 1 1 calc R . .
C17 C 0.3719(7) 0.0272(6) 0.6656(5) 0.0268(17) Uani 1 1 d . . .
H17 H 0.4347 -0.0383 0.6557 0.032 Uiso 1 1 calc R . .
C18 C 0.4046(7) 0.1238(6) 0.6704(4) 0.0251(16) Uani 1 1 d . . .
H18 H 0.4894 0.1232 0.6619 0.030 Uiso 1 1 calc R . .
C19 C 0.0518(7) 0.6149(6) 0.7333(4) 0.0216(15) Uani 1 1 d . . .
H19A H -0.0331 0.6697 0.7205 0.026 Uiso 1 1 calc R . .
H19B H 0.1075 0.6364 0.6867 0.026 Uiso 1 1 calc R . .
C20 C 0.0995(6) 0.6288(6) 0.8155(4) 0.0213(15) Uani 1 1 d . . .
C21 C 0.3874(6) 0.6866(5) 0.7066(4) 0.0171(14) Uani 1 1 d . . .
H21 H 0.3953 0.7439 0.7314 0.021 Uiso 1 1 calc R . .
C22 C 0.3611(6) 0.7028(6) 0.6230(4) 0.0200(15) Uani 1 1 d . . .
H22 H 0.3455 0.7719 0.5803 0.024 Uiso 1 1 calc R . .
C23 C 0.3627(6) 0.5932(6) 0.6150(4) 0.0153(14) Uani 1 1 d . . .
C24 C 0.3444(6) 0.5487(6) 0.5427(4) 0.0148(14) Uani 1 1 d . . .
C25 C 0.3308(6) 0.6125(6) 0.4596(4) 0.0168(14) Uani 1 1 d . . .
H25 H 0.3313 0.6899 0.4458 0.020 Uiso 1 1 calc R . .
C26 C 0.3166(6) 0.5613(6) 0.3968(4) 0.0242(16) Uani 1 1 d . . .
H26 H 0.3069 0.6033 0.3399 0.029 Uiso 1 1 calc R . .
C27 C 0.3168(6) 0.4457(6) 0.4198(4) 0.0214(15) Uani 1 1 d . . .
H27 H 0.3080 0.4090 0.3782 0.026 Uiso 1 1 calc R . .
C28 C 0.3302(6) 0.3853(6) 0.5047(4) 0.0166(14) Uani 1 1 d . . .
H28 H 0.3305 0.3077 0.5198 0.020 Uiso 1 1 calc R . .
C29 C 0.4372(6) 0.5143(6) 0.8350(4) 0.0138(14) Uani 1 1 d . . .
H29A H 0.3956 0.4537 0.8541 0.017 Uiso 1 1 calc R . .
H29B H 0.4068 0.5691 0.8708 0.017 Uiso 1 1 calc R . .
C30 C 0.5808(6) 0.4591(6) 0.8473(4) 0.0170(15) Uani 1 1 d . . .
O16 O 0.3759(9) 0.1374(9) 0.4498(7) 0.037(2) Uiso 0.50 1 d PD F 1
C31 C 0.2430(11) 0.1823(14) 0.4541(10) 0.037(2) Uiso 0.50 1 d PD F 1
O16A O 0.6302(10) 0.0486(9) 0.5269(6) 0.033(2) Uiso 0.50 1 d P G 2
C31A C 0.7625(15) 0.0188(13) 0.5155(10) 0.033(2) Uiso 0.50 1 d P G 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 O8 1.955(5) . ?
Cu1 O5 1.960(4) . ?
Cu1 N1 2.005(5) . ?
Cu1 N3 2.018(5) . ?
Cu1 O7 2.239(5) . ?
Cu2 O1 1.961(4) . ?
Cu2 N7 1.999(5) . ?
Cu2 N6 2.004(5) . ?
Cu2 N9 2.051(5) . ?
Cu2 N4 2.241(5) . ?
O1 C10 1.271(7) . ?
O2 C10 1.212(7) . ?
O3 C20 1.228(8) . ?
O4 C20 1.272(8) . ?
O5 C30 1.265(8) . ?
O6 C30 1.238(8) . ?
O7 H7A 0.857(10) . ?
O7 H7B 0.859(10) . ?
O8 H8A 0.860(10) . ?
O8 H8B 0.861(10) . ?
O9 N10 1.227(7) . ?
O10 N10 1.253(7) . ?
O11 N10 1.234(8) . ?
O12 H12A 0.862(10) . ?
O12 H12B 0.861(10) . ?
O13 H13A 0.864(10) . ?
O13 H13B 0.865(10) . ?
O14 H14A 0.860(10) . ?
O14 H14B 0.861(10) . ?
O19A O19A 1.40(2) 2_566 ?
N1 N2 1.343(7) . ?
N1 C3 1.343(8) . ?
N2 C1 1.354(8) . ?
N2 C9 1.455(8) . ?
N3 C8 1.327(8) . ?
N3 C4 1.383(8) . ?
N4 C13 1.330(8) . ?
N4 N5 1.350(7) . ?
N5 C11 1.343(8) . ?
N5 C19 1.467(8) . ?
N6 C14 1.346(8) . ?
N6 C18 1.350(8) . ?
N7 C23 1.345(8) . ?
N7 N8 1.355(7) . ?
N8 C21 1.347(8) . ?
N8 C29 1.438(8) . ?
N9 C28 1.342(8) . ?
N9 C24 1.353(8) . ?
C1 C2 1.370(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.386(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.454(9) . ?
C4 C5 1.369(9) . ?
C5 C6 1.378(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.390(9) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.524(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C12 1.348(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.394(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.467(9) . ?
C14 C15 1.396(9) . ?
C15 C16 1.376(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.358(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.374(10) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.535(9) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C21 C22 1.355(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.393(9) . ?
C22 H22 0.9300 . ?
C23 C24 1.467(9) . ?
C24 C25 1.367(9) . ?
C25 C26 1.371(9) . ?
C25 H25 0.9300 . ?
C26 C27 1.385(10) . ?
C26 H26 0.9300 . ?
C27 C28 1.380(9) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 C30 1.521(8) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
O16 C31 1.396(9) . ?
O16A C31A 1.395(18) . ?

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
O8 Cu1 O5 90.29(18) . . ?
O8 Cu1 N1 170.1(2) . . ?
O5 Cu1 N1 96.61(18) . . ?
O8 Cu1 N3 91.2(2) . . ?
O5 Cu1 N3 166.41(19) . . ?
N1 Cu1 N3 80.5(2) . . ?
O8 Cu1 O7 93.60(19) . . ?
O5 Cu1 O7 95.09(18) . . ?
N1 Cu1 O7 92.82(19) . . ?
N3 Cu1 O7 98.29(19) . . ?
O1 Cu2 N7 97.07(19) . . ?
O1 Cu2 N6 89.87(19) . . ?
N7 Cu2 N6 172.7(2) . . ?
O1 Cu2 N9 159.33(19) . . ?
N7 Cu2 N9 80.0(2) . . ?
N6 Cu2 N9 94.2(2) . . ?
O1 Cu2 N4 106.73(18) . . ?
N7 Cu2 N4 97.6(2) . . ?
N6 Cu2 N4 78.2(2) . . ?
N9 Cu2 N4 93.9(2) . . ?
C10 O1 Cu2 113.3(4) . . ?
C30 O5 Cu1 120.2(4) . . ?
Cu1 O7 H7A 138(5) . . ?
Cu1 O7 H7B 114(5) . . ?
H7A O7 H7B 101(7) . . ?
Cu1 O8 H8A 110(5) . . ?
Cu1 O8 H8B 111(5) . . ?
H8A O8 H8B 107(7) . . ?
H12A O12 H12B 94(7) . . ?
H13A O13 H13B 103.8(17) . . ?
H14A O14 H14B 92(9) . . ?
N2 N1 C3 105.9(5) . . ?
N2 N1 Cu1 139.1(4) . . ?
C3 N1 Cu1 114.9(4) . . ?
N1 N2 C1 110.7(5) . . ?
N1 N2 C9 121.5(5) . . ?
C1 N2 C9 127.8(5) . . ?
C8 N3 C4 117.6(5) . . ?
C8 N3 Cu1 127.4(4) . . ?
C4 N3 Cu1 114.9(4) . . ?
C13 N4 N5 104.9(5) . . ?
C13 N4 Cu2 109.5(4) . . ?
N5 N4 Cu2 145.5(4) . . ?
C11 N5 N4 111.0(5) . . ?
C11 N5 C19 126.8(6) . . ?
N4 N5 C19 121.9(5) . . ?
C14 N6 C18 118.6(6) . . ?
C14 N6 Cu2 118.1(4) . . ?
C18 N6 Cu2 123.4(5) . . ?
C23 N7 N8 106.5(5) . . ?
C23 N7 Cu2 114.6(4) . . ?
N8 N7 Cu2 137.6(4) . . ?
C21 N8 N7 109.2(5) . . ?
C21 N8 C29 129.7(5) . . ?
N7 N8 C29 120.7(5) . . ?
C28 N9 C24 118.5(5) . . ?
C28 N9 Cu2 126.9(4) . . ?
C24 N9 Cu2 114.6(4) . . ?
O9 N10 O11 120.4(6) . . ?
O9 N10 O10 120.7(6) . . ?
O11 N10 O10 118.9(6) . . ?
N2 C1 C2 107.5(6) . . ?
N2 C1 H1 126.2 . . ?
C2 C1 H1 126.2 . . ?
C1 C2 C3 105.3(6) . . ?
C1 C2 H2 127.3 . . ?
C3 C2 H2 127.3 . . ?
N1 C3 C2 110.5(6) . . ?
N1 C3 C4 116.7(5) . . ?
C2 C3 C4 132.8(6) . . ?
C5 C4 N3 121.8(6) . . ?
C5 C4 C3 125.2(6) . . ?
N3 C4 C3 113.0(5) . . ?
C4 C5 C6 119.2(6) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 119.9(6) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 118.0(6) . . ?
C6 C7 H7 121.0 . . ?
C8 C7 H7 121.0 . . ?
N3 C8 C7 123.4(6) . . ?
N3 C8 H8 118.3 . . ?
C7 C8 H8 118.3 . . ?
N2 C9 C10 112.3(5) . . ?
N2 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N2 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
O2 C10 O1 124.8(6) . . ?
O2 C10 C9 122.4(6) . . ?
O1 C10 C9 112.8(5) . . ?
N5 C11 C12 108.1(6) . . ?
N5 C11 H11 125.9 . . ?
C12 C11 H11 125.9 . . ?
C11 C12 C13 104.9(6) . . ?
C11 C12 H12 127.5 . . ?
C13 C12 H12 127.5 . . ?
N4 C13 C12 111.0(6) . . ?
N4 C13 C14 118.2(6) . . ?
C12 C13 C14 130.7(6) . . ?
N6 C14 C15 121.0(6) . . ?
N6 C14 C13 115.9(6) . . ?
C15 C14 C13 123.1(6) . . ?
C16 C15 C14 119.5(7) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 118.9(7) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 120.0(7) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
N6 C18 C17 121.9(7) . . ?
N6 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
N5 C19 C20 115.6(5) . . ?
N5 C19 H19A 108.4 . . ?
C20 C19 H19A 108.4 . . ?
N5 C19 H19B 108.4 . . ?
C20 C19 H19B 108.4 . . ?
H19A C19 H19B 107.5 . . ?
O3 C20 O4 128.3(6) . . ?
O3 C20 C19 118.6(6) . . ?
O4 C20 C19 113.1(6) . . ?
N8 C21 C22 109.3(6) . . ?
N8 C21 H21 125.3 . . ?
C22 C21 H21 125.3 . . ?
C21 C22 C23 104.9(6) . . ?
C21 C22 H22 127.5 . . ?
C23 C22 H22 127.5 . . ?
N7 C23 C22 110.0(6) . . ?
N7 C23 C24 116.4(6) . . ?
C22 C23 C24 133.6(6) . . ?
N9 C24 C25 122.4(6) . . ?
N9 C24 C23 113.3(5) . . ?
C25 C24 C23 124.3(6) . . ?
C24 C25 C26 119.4(6) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C25 C26 C27 118.8(6) . . ?
C25 C26 H26 120.6 . . ?
C27 C26 H26 120.6 . . ?
C28 C27 C26 119.6(6) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
N9 C28 C27 121.4(6) . . ?
N9 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
N8 C29 C30 113.7(5) . . ?
N8 C29 H29A 108.8 . . ?
C30 C29 H29A 108.8 . . ?
N8 C29 H29B 108.8 . . ?
C30 C29 H29B 108.8 . . ?
H29A C29 H29B 107.7 . . ?
O6 C30 O5 125.8(6) . . ?
O6 C30 C29 119.1(6) . . ?
O5 C30 C29 115.1(5) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.464
_refine_diff_density_min         -1.227
_refine_diff_density_rms         0.125
_database_code_depnum_ccdc_archive 'CCDC 1021991'
#######################################################################
#
#                 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_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H30 Cu2 N6 O14 S2, 2(C O H4)'
_chemical_formula_sum            'C26 H38 Cu2 N6 O16 S2'
_chemical_formula_weight         881.82

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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9313(5)
_cell_length_b                   10.6591(8)
_cell_length_c                   10.9968(6)
_cell_angle_alpha                112.268(6)
_cell_angle_beta                 114.296(6)
_cell_angle_gamma                96.811(5)
_cell_volume                     928.42(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    3882
_cell_measurement_theta_min      3.4120
_cell_measurement_theta_max      28.1300

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             454
_exptl_absorpt_coefficient_mu    1.334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6904
_exptl_absorpt_correction_T_max  0.8250
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(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  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8269
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         25.49
_reflns_number_total             3449
_reflns_number_gt                2917
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0421P)²+0.4148P] 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         3449
_refine_ls_number_parameters     240
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.26731(4) 0.48508(3) 0.10815(4) 0.02382(13) Uani 1 1 d . . .
S1 S 0.05578(8) 0.65958(7) 0.19491(8) 0.02589(18) Uani 1 1 d . A .
O1 O 0.1350(3) -0.0424(3) -0.0507(3) 0.0568(7) Uani 1 1 d . . .
O2 O 0.3866(3) 0.0780(3) 0.1149(4) 0.0671(8) Uani 1 1 d . . .
O3 O 0.2265(3) 0.4163(3) 0.2592(4) 0.0654(8) Uani 1 1 d D . .
H3A H 0.163(4) 0.461(4) 0.264(5) 0.079 Uiso 1 1 d D . .
O4 O 0.1616(2) 0.6268(2) 0.1321(2) 0.0292(5) Uani 1 1 d . . .
O5 O 0.0145(2) 0.5516(2) 0.2353(2) 0.0364(5) Uani 1 1 d . . .
O6 O -0.0867(2) 0.6621(2) 0.0766(3) 0.0401(5) Uani 1 1 d . . .
O7 O 0.1316(3) 0.8029(2) 0.3234(2) 0.0434(6) Uani 1 1 d . . .
N1 N 0.4086(3) 0.3731(2) 0.0734(3) 0.0241(5) Uani 1 1 d . . .
N2 N 0.3959(3) 0.2413(2) -0.0237(3) 0.0273(5) Uani 1 1 d . A .
N3 N 0.4781(3) 0.6386(2) 0.2602(3) 0.0268(5) Uani 1 1 d . . .
C1 C 0.5351(3) 0.2395(3) -0.0148(4) 0.0308(7) Uani 1 1 d . . .
H1 H 0.5554 0.1596 -0.0701 0.037 Uiso 1 1 calc R A .
C2 C 0.6414(3) 0.3726(3) 0.0876(4) 0.0317(7) Uani 1 1 d . A .
H2 H 0.7474 0.4036 0.1160 0.038 Uiso 1 1 calc R . .
C3 C 0.5585(3) 0.4527(3) 0.1409(3) 0.0243(6) Uani 1 1 d . A .
C4 C 0.6007(3) 0.6022(3) 0.2516(3) 0.0265(6) Uani 1 1 d . A .
C5 C 0.7506(4) 0.6983(3) 0.3414(4) 0.0356(7) Uani 1 1 d . . .
H5 H 0.8344 0.6716 0.3326 0.043 Uiso 1 1 calc R A .
C6 C 0.7746(4) 0.8353(4) 0.4451(4) 0.0431(8) Uani 1 1 d . A .
H6 H 0.8757 0.9025 0.5090 0.052 Uiso 1 1 calc R . .
C7 C 0.6508(4) 0.8721(3) 0.4541(4) 0.0447(9) Uani 1 1 d . . .
H7 H 0.6657 0.9651 0.5232 0.054 Uiso 1 1 calc R A .
C8 C 0.5040(4) 0.7717(3) 0.3609(4) 0.0372(7) Uani 1 1 d . A .
H8 H 0.4191 0.7974 0.3680 0.045 Uiso 1 1 calc R . .
C9 C 0.2581(4) 0.1194(3) -0.0974(4) 0.0335(7) Uani 1 1 d . . .
H9A H 0.2463 0.0484 -0.1927 0.040 Uiso 1 1 calc R A .
H9B H 0.1654 0.1500 -0.1211 0.040 Uiso 1 1 calc R . .
C10 C 0.2712(4) 0.0523(3) 0.0045(4) 0.0378(8) Uani 1 1 d . A .
C11 C 0.1303(5) -0.1166(5) 0.0351(6) 0.0776(15) Uani 1 1 d . . .
H11A H 0.2020 -0.1713 0.0385 0.116 Uiso 1 1 calc R . .
H11B H 0.0251 -0.1811 -0.0133 0.116 Uiso 1 1 calc R . .
H11C H 0.1605 -0.0472 0.1373 0.116 Uiso 1 1 calc R . .
C12 C 0.2543(11) 0.3316(10) 0.3280(10) 0.060(2) Uiso 0.50 1 d P A 1
H12A H 0.3452 0.3051 0.3309 0.090 Uiso 0.50 1 calc PR A 1
H12B H 0.1642 0.2458 0.2715 0.090 Uiso 0.50 1 calc PR A 1
H12C H 0.2731 0.3839 0.4304 0.090 Uiso 0.50 1 calc PR A 1
C12A C 0.3259(14) 0.4041(13) 0.3805(13) 0.087(3) Uiso 0.50 1 d P A 2
H12D H 0.2664 0.3481 0.4046 0.130 Uiso 0.50 1 calc PR A 2
H12E H 0.3863 0.4988 0.4668 0.130 Uiso 0.50 1 calc PR A 2
H12F H 0.3960 0.3567 0.3567 0.130 Uiso 0.50 1 calc PR A 2
O8 O 0.1332(7) 0.8368(6) 0.5914(6) 0.0376(13) Uiso 0.50 1 d P B 1
H8A H 0.1386 0.8276 0.5134 0.045 Uiso 0.50 1 d PR B 1
C13 C 0.1564(13) 0.7263(12) 0.6241(13) 0.067(3) Uiso 0.50 1 d P B 1
H13A H 0.2617 0.7249 0.6486 0.101 Uiso 0.50 1 calc PR B 1
H13B H 0.0818 0.6361 0.5369 0.101 Uiso 0.50 1 calc PR B 1
H13C H 0.1421 0.7399 0.7098 0.101 Uiso 0.50 1 calc PR B 1
O8A O 0.1843(8) 0.8577(8) 0.6009(8) 0.065(2) Uiso 0.50 1 d P C 2
H8B H 0.1543 0.8327 0.5083 0.079 Uiso 0.50 1 d PR C 2
C13A C 0.2161(14) 0.7445(13) 0.6277(15) 0.084(4) Uiso 0.50 1 d P C 2
H13D H 0.2756 0.7049 0.5805 0.126 Uiso 0.50 1 calc PR C 2
H13E H 0.1188 0.6707 0.5853 0.126 Uiso 0.50 1 calc PR C 2
H13F H 0.2763 0.7786 0.7359 0.126 Uiso 0.50 1 calc PR C 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 O6 1.930(2) 2_565 ?
Cu1 O4 1.9376(19) . ?
Cu1 N1 2.008(2) . ?
Cu1 N3 2.022(2) . ?
Cu1 O3 2.207(2) . ?
S1 O7 1.453(2) . ?
S1 O5 1.455(2) . ?
S1 O4 1.4855(19) . ?
S1 O6 1.488(2) . ?
O1 C10 1.324(4) . ?
O1 C11 1.453(5) . ?
O2 C10 1.179(4) . ?
O3 C12A 1.359(11) . ?
O3 C12 1.366(9) . ?
O3 H3A 0.844(10) . ?
O6 Cu1 1.930(2) 2_565 ?
N1 C3 1.342(3) . ?
N1 N2 1.356(3) . ?
N2 C1 1.349(4) . ?
N2 C9 1.444(3) . ?
N3 C8 1.340(4) . ?
N3 C4 1.350(4) . ?
C1 C2 1.361(4) . ?
C1 H1 0.9400 . ?
C2 C3 1.390(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.466(4) . ?
C4 C5 1.379(4) . ?
C5 C6 1.386(5) . ?
C5 H5 0.9400 . ?
C6 C7 1.364(5) . ?
C6 H6 0.9400 . ?
C7 C8 1.375(4) . ?
C7 H7 0.9400 . ?
C8 H8 0.9400 . ?
C9 C10 1.515(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C12A H12D 0.9700 . ?
C12A H12E 0.9700 . ?
C12A H12F 0.9700 . ?
O8 C13 1.373(12) . ?
O8 H8A 0.8500 . ?
O8 H8B 1.0050 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
O8A C13A 1.388(13) . ?
O8A H8A 0.7784 . ?
O8A H8B 0.8500 . ?
C13A H13D 0.9700 . ?
C13A H13E 0.9700 . ?
C13A H13F 0.9700 . ?

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
O6 Cu1 O4 93.97(9) 2_565 . ?
O6 Cu1 N1 91.72(9) 2_565 . ?
O4 Cu1 N1 164.82(8) . . ?
O6 Cu1 N3 163.61(9) 2_565 . ?
O4 Cu1 N3 91.20(9) . . ?
N1 Cu1 N3 79.69(9) . . ?
O6 Cu1 O3 95.65(11) 2_565 . ?
O4 Cu1 O3 95.11(9) . . ?
N1 Cu1 O3 98.31(9) . . ?
N3 Cu1 O3 99.36(11) . . ?
O7 S1 O5 112.33(13) . . ?
O7 S1 O4 108.56(12) . . ?
O5 S1 O4 110.61(12) . . ?
O7 S1 O6 107.33(14) . . ?
O5 S1 O6 110.35(12) . . ?
O4 S1 O6 107.49(12) . . ?
C10 O1 C11 116.2(3) . . ?
C12A O3 C12 33.8(5) . . ?
C12A O3 Cu1 131.6(5) . . ?
C12 O3 Cu1 146.1(4) . . ?
C12A O3 H3A 121(3) . . ?
C12 O3 H3A 120(3) . . ?
Cu1 O3 H3A 93(3) . . ?
S1 O4 Cu1 134.75(12) . . ?
S1 O6 Cu1 133.74(13) . 2_565 ?
C3 N1 N2 105.3(2) . . ?
C3 N1 Cu1 114.72(18) . . ?
N2 N1 Cu1 138.29(19) . . ?
C1 N2 N1 110.3(2) . . ?
C1 N2 C9 127.2(2) . . ?
N1 N2 C9 121.3(2) . . ?
C8 N3 C4 118.6(3) . . ?
C8 N3 Cu1 126.0(2) . . ?
C4 N3 Cu1 115.27(19) . . ?
N2 C1 C2 108.5(3) . . ?
N2 C1 H1 125.7 . . ?
C2 C1 H1 125.7 . . ?
C1 C2 C3 104.8(3) . . ?
C1 C2 H2 127.6 . . ?
C3 C2 H2 127.6 . . ?
N1 C3 C2 111.1(3) . . ?
N1 C3 C4 115.4(2) . . ?
C2 C3 C4 133.6(3) . . ?
N3 C4 C5 122.1(3) . . ?
N3 C4 C3 113.6(2) . . ?
C5 C4 C3 124.4(3) . . ?
C4 C5 C6 118.3(3) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C7 C6 C5 119.7(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 119.3(3) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
N3 C8 C7 122.0(3) . . ?
N3 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
N2 C9 C10 110.1(3) . . ?
N2 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
N2 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.2 . . ?
O2 C10 O1 124.9(3) . . ?
O2 C10 C9 125.0(3) . . ?
O1 C10 C9 110.0(3) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
O3 C12A H12D 109.5 . . ?
O3 C12A H12E 109.5 . . ?
H12D C12A H12E 109.5 . . ?
O3 C12A H12F 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
C13 O8 H8A 113.5 . . ?
C13 O8 H8B 113.3 . . ?
H8A O8 H8B 7.3 . . ?
C13A O8A H8A 107.0 . . ?
C13A O8A H8B 108.4 . . ?
H8A O8A H8B 12.8 . . ?
O8A C13A H13D 109.5 . . ?
O8A C13A H13E 109.5 . . ?
H13D C13A H13E 109.5 . . ?
O8A C13A H13F 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 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
O6 Cu1 O3 C12A 137.8(7) 2_565 . . . ?
O4 Cu1 O3 C12A -127.7(7) . . . . ?
N1 Cu1 O3 C12A 45.2(7) . . . . ?
N3 Cu1 O3 C12A -35.6(7) . . . . ?
O6 Cu1 O3 C12 89.9(8) 2_565 . . . ?
O4 Cu1 O3 C12 -175.6(8) . . . . ?
N1 Cu1 O3 C12 -2.7(8) . . . . ?
N3 Cu1 O3 C12 -83.5(8) . . . . ?
O7 S1 O4 Cu1 117.66(19) . . . . ?
O5 S1 O4 Cu1 -6.0(2) . . . . ?
O6 S1 O4 Cu1 -126.54(17) . . . . ?
O6 Cu1 O4 S1 82.55(19) 2_565 . . . ?
N1 Cu1 O4 S1 -165.7(3) . . . . ?
N3 Cu1 O4 S1 -113.01(18) . . . . ?
O3 Cu1 O4 S1 -13.5(2) . . . . ?
O7 S1 O6 Cu1 -167.23(17) . . . 2_565 ?
O5 S1 O6 Cu1 -44.5(2) . . . 2_565 ?
O4 S1 O6 Cu1 76.2(2) . . . 2_565 ?
O6 Cu1 N1 C3 155.07(19) 2_565 . . . ?
O4 Cu1 N1 C3 43.0(4) . . . . ?
N3 Cu1 N1 C3 -10.88(18) . . . . ?
O3 Cu1 N1 C3 -109.0(2) . . . . ?
O6 Cu1 N1 N2 -7.4(3) 2_565 . . . ?
O4 Cu1 N1 N2 -119.5(3) . . . . ?
N3 Cu1 N1 N2 -173.4(3) . . . . ?
O3 Cu1 N1 N2 88.6(3) . . . . ?
C3 N1 N2 C1 0.7(3) . . . . ?
Cu1 N1 N2 C1 164.2(2) . . . . ?
C3 N1 N2 C9 168.9(2) . . . . ?
Cu1 N1 N2 C9 -27.5(4) . . . . ?
O6 Cu1 N3 C8 125.8(3) 2_565 . . . ?
O4 Cu1 N3 C8 17.4(2) . . . . ?
N1 Cu1 N3 C8 -174.8(3) . . . . ?
O3 Cu1 N3 C8 -78.0(3) . . . . ?
O6 Cu1 N3 C4 -50.7(4) 2_565 . . . ?
O4 Cu1 N3 C4 -159.2(2) . . . . ?
N1 Cu1 N3 C4 8.6(2) . . . . ?
O3 Cu1 N3 C4 105.4(2) . . . . ?
N1 N2 C1 C2 -1.1(3) . . . . ?
C9 N2 C1 C2 -168.5(3) . . . . ?
N2 C1 C2 C3 1.0(3) . . . . ?
N2 N1 C3 C2 0.0(3) . . . . ?
Cu1 N1 C3 C2 -168.01(18) . . . . ?
N2 N1 C3 C4 179.5(2) . . . . ?
Cu1 N1 C3 C4 11.5(3) . . . . ?
C1 C2 C3 N1 -0.6(3) . . . . ?
C1 C2 C3 C4 -180.0(3) . . . . ?
C8 N3 C4 C5 -0.8(4) . . . . ?
Cu1 N3 C4 C5 176.0(2) . . . . ?
C8 N3 C4 C3 178.2(2) . . . . ?
Cu1 N3 C4 C3 -5.0(3) . . . . ?
N1 C3 C4 N3 -4.2(3) . . . . ?
C2 C3 C4 N3 175.1(3) . . . . ?
N1 C3 C4 C5 174.7(3) . . . . ?
C2 C3 C4 C5 -6.0(5) . . . . ?
N3 C4 C5 C6 1.1(4) . . . . ?
C3 C4 C5 C6 -177.8(3) . . . . ?
C4 C5 C6 C7 -1.0(5) . . . . ?
C5 C6 C7 C8 0.8(5) . . . . ?
C4 N3 C8 C7 0.5(5) . . . . ?
Cu1 N3 C8 C7 -175.9(2) . . . . ?
C6 C7 C8 N3 -0.5(5) . . . . ?
C1 N2 C9 C10 81.1(4) . . . . ?
N1 N2 C9 C10 -85.1(3) . . . . ?
C11 O1 C10 O2 1.1(5) . . . . ?
C11 O1 C10 C9 179.5(3) . . . . ?
N2 C9 C10 O2 -12.8(5) . . . . ?
N2 C9 C10 O1 168.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.069
_database_code_depnum_ccdc_archive 'CCDC 1021992'
#######################################################################
#
#                 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_4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C43 H41 Cl Cu2 N12 O12, 2(Cl O4), C O H4'
_chemical_formula_sum            'C44 H45 Cl3 Cu2 N12 O21'
_chemical_formula_weight         1311.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.2169(3)
_cell_length_b                   14.6198(5)
_cell_length_c                   15.2117(5)
_cell_angle_alpha                75.840(3)
_cell_angle_beta                 79.165(2)
_cell_angle_gamma                78.964(2)
_cell_volume                     2766.38(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    12364
_cell_measurement_theta_min      3.1550
_cell_measurement_theta_max      73.7790

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1340
_exptl_absorpt_coefficient_mu    3.044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3134
_exptl_absorpt_correction_T_max  0.4642
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4692
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24860
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         67.07
_reflns_number_total             9869
_reflns_number_gt                8585
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.1430P)²+6.9205P] 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         9869
_refine_ls_number_parameters     760
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0717
_refine_ls_wR_factor_ref         0.2267
_refine_ls_wR_factor_gt          0.2186
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.053
_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 0.37245(5) 0.07469(4) 0.32124(4) 0.0268(2) Uani 1 1 d . . .
Cu2 Cu 0.09432(4) 0.35705(4) 0.27659(4) 0.02433(19) Uani 1 1 d . . .
Cl1 Cl 0.60564(13) 0.37065(11) 0.17030(10) 0.0553(4) Uani 1 1 d . . .
Cl2 Cl 0.07041(8) 0.21954(7) 0.51585(7) 0.0307(3) Uani 1 1 d . . .
Cl3 Cl 0.5000 0.5000 0.5000 0.0962(12) Uani 1 2 d SD . .
Cl4 Cl 0.9815(3) 0.9672(3) 0.0254(3) 0.0756(9) Uiso 0.50 1 d PD . .
O1 O 0.6456(4) 0.0385(4) 0.1708(3) 0.0715(14) Uani 1 1 d . . .
O2 O 0.6139(4) 0.0484(4) 0.0287(3) 0.0700(14) Uani 1 1 d D . .
O3 O 0.2071(3) -0.2021(3) 0.5278(3) 0.0456(9) Uani 1 1 d . . .
O4 O 0.2554(3) -0.2026(3) 0.3779(3) 0.0485(9) Uani 1 1 d . . .
O5 O 0.3701(2) 0.1980(2) 0.3530(2) 0.0275(6) Uani 1 1 d . . .
O6 O 0.2204(2) 0.2613(2) 0.3021(2) 0.0258(6) Uani 1 1 d . . .
O7 O 0.2226(3) 0.6520(3) 0.1663(3) 0.0557(11) Uani 1 1 d . . .
O8 O 0.0805(3) 0.6273(3) 0.1205(3) 0.0500(9) Uani 1 1 d . . .
O9 O 0.5754(6) 0.3095(4) 0.2518(4) 0.0928(19) Uani 1 1 d . . .
O10 O 0.6472(5) 0.3234(5) 0.0982(4) 0.0849(17) Uani 1 1 d . . .
O11 O 0.5057(7) 0.4280(6) 0.1514(6) 0.128(3) Uani 1 1 d . . .
O12 O 0.6742(7) 0.4254(8) 0.1838(6) 0.165(5) Uani 1 1 d . . .
O13 O 0.1688(3) 0.2489(3) 0.5158(3) 0.0389(8) Uani 1 1 d . . .
O14 O 0.0121(3) 0.2906(3) 0.4524(3) 0.0407(8) Uani 1 1 d . . .
O15 O 0.0886(3) 0.1298(3) 0.4879(3) 0.0445(9) Uani 1 1 d . . .
O16 O 0.0103(3) 0.2105(3) 0.6061(3) 0.0462(9) Uani 1 1 d . . .
O17 O 0.4832(11) 0.4225(8) 0.4682(11) 0.091(4) Uani 0.50 1 d P . .
O18 O 0.5549(17) 0.5573(16) 0.4817(15) 0.061(5) Uiso 0.25 1 d P . .
O18A O 0.593(4) 0.445(3) 0.492(3) 0.148(14) Uiso 0.25 1 d P . .
O19 O 0.4518(11) 0.5722(9) 0.4067(9) 0.096(4) Uani 0.50 1 d P . .
O20 O 0.6012(8) 0.5038(12) 0.4459(10) 0.100(4) Uiso 0.50 1 d PD . .
O21 O 1.0699(14) 0.8979(14) 0.0370(18) 0.169(9) Uiso 0.50 1 d PD . 1
O22 O 0.9594(14) 0.9770(13) 0.1190(7) 0.054(4) Uiso 0.25 1 d PD . 1
O23 O 0.9109(9) 0.9078(8) 0.0156(9) 0.088(3) Uiso 0.50 1 d PD . 1
O24 O 0.910(3) 0.927(4) 0.101(3) 0.19(2) Uiso 0.25 1 d PD . 1
O22A O 0.945(3) 1.030(3) 0.070(3) 0.119(10) Uiso 0.25 1 d P . 2
O24A O 1.0738(14) 0.9423(15) 0.0021(14) 0.057(4) Uiso 0.25 1 d P . 2
O25 O 0.5519(5) 0.6325(4) 0.1837(5) 0.0839(16) Uani 1 1 d . . .
N1 N 0.4671(3) -0.0541(3) 0.3060(3) 0.0354(9) Uani 1 1 d . . .
N2 N 0.5181(4) -0.1024(4) 0.2412(4) 0.0523(12) Uani 1 1 d . A .
N3 N 0.3743(3) 0.0078(3) 0.4526(3) 0.0293(8) Uani 1 1 d . . .
N4 N 0.2327(3) 0.0352(3) 0.2936(3) 0.0318(8) Uani 1 1 d . . .
N5 N 0.1569(3) -0.0188(3) 0.3298(3) 0.0386(9) Uani 1 1 d . . .
N6 N 0.3720(3) 0.1405(3) 0.1895(3) 0.0304(8) Uani 1 1 d . . .
N7 N 0.1379(3) 0.4045(3) 0.1268(3) 0.0313(8) Uani 1 1 d . . .
N8 N 0.1891(3) 0.4667(3) 0.0615(3) 0.0358(9) Uani 1 1 d . . .
N9 N 0.0229(3) 0.2746(3) 0.2292(3) 0.0288(8) Uani 1 1 d . . .
N10 N 0.1467(3) 0.4411(3) 0.3313(3) 0.0262(7) Uani 1 1 d . . .
N11 N 0.2352(3) 0.4326(3) 0.3652(3) 0.0268(7) Uani 1 1 d . . .
N12 N -0.0369(3) 0.4579(3) 0.2926(3) 0.0281(8) Uani 1 1 d . . .
C1 C 0.5527(6) -0.1935(5) 0.2808(6) 0.0671(19) Uani 1 1 d . . .
H1 H 0.5896 -0.2405 0.2495 0.080 Uiso 1 1 calc R . .
C2 C 0.5259(5) -0.2062(4) 0.3724(5) 0.0571(16) Uani 1 1 d . . .
H2 H 0.5395 -0.2623 0.4172 0.069 Uiso 1 1 calc R . .
C3 C 0.4730(4) -0.1167(4) 0.3857(4) 0.0386(11) Uani 1 1 d . . .
C4 C 0.4228(3) -0.0838(3) 0.4683(4) 0.0347(10) Uani 1 1 d . . .
C5 C 0.4240(4) -0.1381(4) 0.5567(4) 0.0435(12) Uani 1 1 d . . .
H5 H 0.4574 -0.2018 0.5671 0.052 Uiso 1 1 calc R . .
C6 C 0.3750(4) -0.0970(4) 0.6296(4) 0.0471(13) Uani 1 1 d . . .
H6 H 0.3754 -0.1328 0.6900 0.057 Uiso 1 1 calc R . .
C7 C 0.3258(4) -0.0039(4) 0.6140(4) 0.0454(13) Uani 1 1 d . . .
H7 H 0.2921 0.0247 0.6629 0.055 Uiso 1 1 calc R . .
C8 C 0.3273(4) 0.0463(4) 0.5246(3) 0.0376(11) Uani 1 1 d . . .
H8 H 0.2942 0.1100 0.5133 0.045 Uiso 1 1 calc R . .
C9 C 0.5305(5) -0.0576(5) 0.1454(4) 0.0562(16) Uani 1 1 d . . .
H9A H 0.4623 -0.0253 0.1291 0.067 Uiso 1 1 calc R A .
H9B H 0.5555 -0.1070 0.1097 0.067 Uiso 1 1 calc R . .
C10 C 0.6046(5) 0.0133(6) 0.1193(4) 0.0592(17) Uani 1 1 d . A .
C11 C 0.6698(15) 0.1305(12) -0.0129(14) 0.073(5) Uiso 0.50 1 d PD A 1
H11A H 0.6620 0.1707 0.0309 0.110 Uiso 0.50 1 calc PR A 1
H11B H 0.6410 0.1671 -0.0673 0.110 Uiso 0.50 1 calc PR A 1
H11C H 0.7431 0.1076 -0.0295 0.110 Uiso 0.50 1 calc PR A 1
C11A C 0.6957(13) 0.1058(14) -0.0040(14) 0.073(5) Uiso 0.50 1 d PD A 2
H11D H 0.6709 0.1691 0.0079 0.110 Uiso 0.50 1 calc PR A 2
H11E H 0.7162 0.1105 -0.0694 0.110 Uiso 0.50 1 calc PR A 2
H11F H 0.7551 0.0765 0.0274 0.110 Uiso 0.50 1 calc PR A 2
C12 C 0.1030(5) -0.0243(4) 0.2646(5) 0.0535(15) Uani 1 1 d . . .
H12 H 0.0477 -0.0593 0.2739 0.064 Uiso 1 1 calc R . .
C13 C 0.1417(5) 0.0289(4) 0.1839(5) 0.0508(15) Uani 1 1 d . . .
H13 H 0.1190 0.0397 0.1267 0.061 Uiso 1 1 calc R . .
C14 C 0.2245(4) 0.0649(3) 0.2051(4) 0.0363(11) Uani 1 1 d . . .
C15 C 0.2950(4) 0.1285(3) 0.1479(3) 0.0351(10) Uani 1 1 d . . .
C16 C 0.2835(5) 0.1768(4) 0.0589(4) 0.0451(13) Uani 1 1 d . . .
H16 H 0.2308 0.1662 0.0305 0.054 Uiso 1 1 calc R . .
C17 C 0.3500(5) 0.2403(4) 0.0127(4) 0.0510(14) Uani 1 1 d . . .
H17 H 0.3435 0.2732 -0.0478 0.061 Uiso 1 1 calc R . .
C18 C 0.4264(5) 0.2554(4) 0.0561(4) 0.0491(13) Uani 1 1 d . . .
H18 H 0.4711 0.3002 0.0264 0.059 Uiso 1 1 calc R . .
C19 C 0.4359(4) 0.2035(4) 0.1440(3) 0.0380(11) Uani 1 1 d . . .
H19 H 0.4889 0.2126 0.1730 0.046 Uiso 1 1 calc R . .
C20 C 0.1464(4) -0.0667(4) 0.4243(4) 0.0402(11) Uani 1 1 d . . .
H20A H 0.0729 -0.0721 0.4472 0.048 Uiso 1 1 calc R . .
H20B H 0.1691 -0.0288 0.4599 0.048 Uiso 1 1 calc R . .
C21 C 0.2103(4) -0.1649(4) 0.4377(4) 0.0361(11) Uani 1 1 d . . .
C22 C 0.2612(5) -0.2982(5) 0.5519(5) 0.0575(15) Uani 1 1 d . . .
H22A H 0.2215 -0.3425 0.5407 0.086 Uiso 1 1 calc R . .
H22B H 0.2690 -0.3132 0.6162 0.086 Uiso 1 1 calc R . .
H22C H 0.3294 -0.3034 0.5148 0.086 Uiso 1 1 calc R . .
C23 C 0.2254(4) 0.4978(4) 0.4158(4) 0.0478(14) Uani 1 1 d . . .
H23 H 0.2768 0.5067 0.4467 0.057 Uiso 1 1 calc R . .
C24 C 0.1263(5) 0.5498(5) 0.4145(5) 0.0546(16) Uani 1 1 d . . .
H24 H 0.0964 0.6002 0.4440 0.065 Uiso 1 1 calc R . .
C25 C 0.0811(4) 0.5109(3) 0.3602(3) 0.0327(10) Uani 1 1 d . . .
C26 C -0.0243(4) 0.5242(3) 0.3356(3) 0.0339(10) Uani 1 1 d . . .
C27 C -0.1034(5) 0.5957(5) 0.3549(5) 0.0590(18) Uani 1 1 d . . .
H27 H -0.0921 0.6422 0.3836 0.071 Uiso 1 1 calc R . .
C28 C -0.2004(5) 0.5978(5) 0.3312(6) 0.0643(19) Uani 1 1 d . . .
H28 H -0.2564 0.6449 0.3453 0.077 Uiso 1 1 calc R . .
C29 C -0.2137(4) 0.5312(4) 0.2875(5) 0.0496(14) Uani 1 1 d . . .
H29 H -0.2786 0.5321 0.2703 0.060 Uiso 1 1 calc R . .
C30 C -0.1306(4) 0.4623(4) 0.2686(4) 0.0357(10) Uani 1 1 d . . .
H30 H -0.1399 0.4168 0.2378 0.043 Uiso 1 1 calc R . .
C31 C 0.3242(3) 0.3611(3) 0.3467(4) 0.0324(10) Uani 1 1 d . . .
H31A H 0.3650 0.3463 0.3973 0.039 Uiso 1 1 calc R . .
H31B H 0.3685 0.3889 0.2910 0.039 Uiso 1 1 calc R . .
C32 C 0.2993(3) 0.2670(3) 0.3341(3) 0.0237(8) Uani 1 1 d . . .
C33 C 0.1695(4) 0.4674(4) -0.0229(3) 0.0427(12) Uani 1 1 d . . .
H33 H 0.1962 0.5055 -0.0785 0.051 Uiso 1 1 calc R . .
C34 C 0.1035(4) 0.4021(4) -0.0121(3) 0.0403(11) Uani 1 1 d . . .
H34 H 0.0761 0.3862 -0.0582 0.048 Uiso 1 1 calc R . .
C35 C 0.0858(3) 0.3644(3) 0.0823(3) 0.0321(9) Uani 1 1 d . . .
C36 C 0.0211(4) 0.2941(3) 0.1377(3) 0.0314(9) Uani 1 1 d . . .
C37 C -0.0417(4) 0.2515(4) 0.1006(4) 0.0418(12) Uani 1 1 d . . .
H37 H -0.0411 0.2645 0.0368 0.050 Uiso 1 1 calc R . .
C38 C -0.1045(5) 0.1902(4) 0.1585(4) 0.0497(14) Uani 1 1 d . . .
H38 H -0.1488 0.1622 0.1348 0.060 Uiso 1 1 calc R . .
C39 C -0.1022(4) 0.1702(4) 0.2511(4) 0.0448(12) Uani 1 1 d . . .
H39 H -0.1447 0.1283 0.2914 0.054 Uiso 1 1 calc R . .
C40 C -0.0366(4) 0.2123(3) 0.2845(4) 0.0349(10) Uani 1 1 d . . .
H40 H -0.0335 0.1969 0.3478 0.042 Uiso 1 1 calc R . .
C41 C 0.2452(4) 0.5290(4) 0.0883(4) 0.0414(12) Uani 1 1 d . . .
H41A H 0.2921 0.5574 0.0349 0.050 Uiso 1 1 calc R . .
H41B H 0.2878 0.4914 0.1348 0.050 Uiso 1 1 calc R . .
C42 C 0.1715(4) 0.6072(4) 0.1261(3) 0.0401(12) Uani 1 1 d . . .
C43 C 0.1612(6) 0.7321(6) 0.2031(6) 0.0689(19) Uani 1 1 d . . .
H43A H 0.1372 0.7823 0.1534 0.103 Uiso 1 1 calc R . .
H43B H 0.2040 0.7565 0.2348 0.103 Uiso 1 1 calc R . .
H43C H 0.1016 0.7109 0.2458 0.103 Uiso 1 1 calc R . .
C44 C 0.4495(15) 0.6155(14) 0.2546(14) 0.085(5) Uiso 0.50 1 d P . .
C44A C 0.4553(16) 0.6488(14) 0.1867(14) 0.084(5) Uiso 0.50 1 d P . .


_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 1.971(3) . ?
Cu1 N6 2.000(4) . ?
Cu1 N3 2.001(4) . ?
Cu1 N1 2.090(4) . ?
Cu1 N4 2.177(4) . ?
Cu2 N10 1.930(3) . ?
Cu2 O6 1.993(3) . ?
Cu2 N9 1.995(4) . ?
Cu2 N12 2.068(4) . ?
Cu2 N7 2.211(4) . ?
Cl1 O9 1.380(5) . ?
Cl1 O12 1.390(6) . ?
Cl1 O10 1.407(6) . ?
Cl1 O11 1.460(8) . ?
Cl2 O15 1.439(3) . ?
Cl2 O16 1.440(4) . ?
Cl2 O13 1.445(3) . ?
Cl2 O14 1.445(4) . ?
Cl3 O18 1.16(2) . ?
Cl3 O18 1.16(2) 2_666 ?
Cl3 O18A 1.33(5) 2_666 ?
Cl3 O18A 1.33(5) . ?
Cl3 O17 1.405(11) 2_666 ?
Cl3 O17 1.405(11) . ?
Cl3 O20 1.436(9) . ?
Cl3 O20 1.436(9) 2_666 ?
Cl3 O19 1.698(11) 2_666 ?
Cl3 O19 1.698(10) . ?
Cl4 Cl4 1.197(8) 2_775 ?
Cl4 O24A 1.214(19) . ?
Cl4 O22A 1.25(4) . ?
Cl4 O24A 1.39(2) 2_775 ?
Cl4 O21 1.399(10) . ?
Cl4 O24 1.427(10) . ?
Cl4 O22 1.435(9) . ?
Cl4 O23 1.440(8) . ?
Cl4 O22A 1.59(4) 2_775 ?
Cl4 O21 2.016(19) 2_775 ?
O1 C10 1.192(8) . ?
O2 C10 1.339(8) . ?
O2 C11A 1.436(9) . ?
O2 C11 1.476(9) . ?
O3 C21 1.341(7) . ?
O3 C22 1.442(7) . ?
O4 C21 1.185(6) . ?
O5 C32 1.256(5) . ?
O6 C32 1.255(5) . ?
O7 C42 1.332(6) . ?
O7 C43 1.460(8) . ?
O8 C42 1.196(7) . ?
O17 O18 0.91(2) 2_666 ?
O18 O17 0.91(2) 2_666 ?
O18A O19 1.52(5) 2_666 ?
O19 O18A 1.52(5) 2_666 ?
O21 Cl4 2.016(19) 2_775 ?
O22A O24A 1.13(4) 2_775 ?
O22A Cl4 1.59(4) 2_775 ?
O24A O22A 1.13(4) 2_775 ?
O24A Cl4 1.39(2) 2_775 ?
O25 C44A 1.25(2) . ?
O25 C44 1.58(2) . ?
N1 C3 1.334(7) . ?
N1 N2 1.353(6) . ?
N2 C1 1.351(9) . ?
N2 C9 1.436(9) . ?
N3 C8 1.347(7) . ?
N3 C4 1.353(6) . ?
N4 C14 1.328(7) . ?
N4 N5 1.347(6) . ?
N5 C12 1.350(7) . ?
N5 C20 1.430(7) . ?
N6 C19 1.345(6) . ?
N6 C15 1.352(6) . ?
N7 C35 1.342(6) . ?
N7 N8 1.346(6) . ?
N8 C33 1.353(7) . ?
N8 C41 1.449(6) . ?
N9 C40 1.344(6) . ?
N9 C36 1.355(6) . ?
N10 C25 1.313(6) . ?
N10 N11 1.338(5) . ?
N11 C23 1.338(6) . ?
N11 C31 1.451(6) . ?
N12 C30 1.342(6) . ?
N12 C26 1.344(6) . ?
C1 C2 1.347(11) . ?
C1 H1 0.9400 . ?
C2 C3 1.403(8) . ?
C2 H2 0.9400 . ?
C3 C4 1.453(8) . ?
C4 C5 1.386(7) . ?
C5 C6 1.384(9) . ?
C5 H5 0.9400 . ?
C6 C7 1.376(9) . ?
C6 H6 0.9400 . ?
C7 C8 1.377(8) . ?
C7 H7 0.9400 . ?
C8 H8 0.9400 . ?
C9 C10 1.494(10) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C11A H11E 0.9700 . ?
C11A H11F 0.9700 . ?
C12 C13 1.351(10) . ?
C12 H12 0.9400 . ?
C13 C14 1.420(7) . ?
C13 H13 0.9400 . ?
C14 C15 1.456(8) . ?
C15 C16 1.387(7) . ?
C16 C17 1.374(9) . ?
C16 H16 0.9400 . ?
C17 C18 1.383(9) . ?
C17 H17 0.9400 . ?
C18 C19 1.381(8) . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?
C20 C21 1.508(7) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C23 C24 1.385(8) . ?
C23 H23 0.9400 . ?
C24 C25 1.382(7) . ?
C24 H24 0.9400 . ?
C25 C26 1.474(6) . ?
C26 C27 1.375(7) . ?
C27 C28 1.388(8) . ?
C27 H27 0.9400 . ?
C28 C29 1.359(9) . ?
C28 H28 0.9400 . ?
C29 C30 1.379(7) . ?
C29 H29 0.9400 . ?
C30 H30 0.9400 . ?
C31 C32 1.537(6) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C33 C34 1.374(8) . ?
C33 H33 0.9400 . ?
C34 C35 1.399(7) . ?
C34 H34 0.9400 . ?
C35 C36 1.462(7) . ?
C36 C37 1.393(7) . ?
C37 C38 1.376(8) . ?
C37 H37 0.9400 . ?
C38 C39 1.372(9) . ?
C38 H38 0.9400 . ?
C39 C40 1.383(7) . ?
C39 H39 0.9400 . ?
C40 H40 0.9400 . ?
C41 C42 1.508(8) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C43 H43C 0.9700 . ?
C44 C44A 1.02(2) . ?

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 N6 90.02(14) . . ?
O5 Cu1 N3 90.40(14) . . ?
N6 Cu1 N3 179.36(17) . . ?
O5 Cu1 N1 143.52(14) . . ?
N6 Cu1 N1 99.99(16) . . ?
N3 Cu1 N1 79.39(16) . . ?
O5 Cu1 N4 121.47(13) . . ?
N6 Cu1 N4 78.88(16) . . ?
N3 Cu1 N4 101.32(15) . . ?
N1 Cu1 N4 94.94(15) . . ?
N10 Cu2 O6 88.41(13) . . ?
N10 Cu2 N9 172.79(15) . . ?
O6 Cu2 N9 96.65(13) . . ?
N10 Cu2 N12 79.37(15) . . ?
O6 Cu2 N12 161.87(14) . . ?
N9 Cu2 N12 94.49(15) . . ?
N10 Cu2 N7 105.90(15) . . ?
O6 Cu2 N7 98.53(14) . . ?
N9 Cu2 N7 78.50(15) . . ?
N12 Cu2 N7 97.67(15) . . ?
O9 Cl1 O12 109.7(5) . . ?
O9 Cl1 O10 113.1(4) . . ?
O12 Cl1 O10 111.9(4) . . ?
O9 Cl1 O11 101.0(5) . . ?
O12 Cl1 O11 111.8(7) . . ?
O10 Cl1 O11 108.8(4) . . ?
O15 Cl2 O16 110.0(2) . . ?
O15 Cl2 O13 109.9(2) . . ?
O16 Cl2 O13 109.9(2) . . ?
O15 Cl2 O14 109.0(2) . . ?
O16 Cl2 O14 108.6(2) . . ?
O13 Cl2 O14 109.5(2) . . ?
O18 Cl3 O18 180.000(5) . 2_666 ?
O18 Cl3 O18A 100(2) . 2_666 ?
O18 Cl3 O18A 80(2) 2_666 2_666 ?
O18 Cl3 O18A 80(2) . . ?
O18 Cl3 O18A 100(2) 2_666 . ?
O18A Cl3 O18A 180(4) 2_666 . ?
O18 Cl3 O17 40.3(11) . 2_666 ?
O18 Cl3 O17 139.7(11) 2_666 2_666 ?
O18A Cl3 O17 75(2) 2_666 2_666 ?
O18A Cl3 O17 105(2) . 2_666 ?
O18 Cl3 O17 139.7(11) . . ?
O18 Cl3 O17 40.3(11) 2_666 . ?
O18A Cl3 O17 105(2) 2_666 . ?
O18A Cl3 O17 75(2) . . ?
O17 Cl3 O17 180.0(4) 2_666 . ?
O18 Cl3 O20 48.1(12) . . ?
O18 Cl3 O20 131.9(12) 2_666 . ?
O18A Cl3 O20 138.8(19) 2_666 . ?
O18A Cl3 O20 41.2(19) . . ?
O17 Cl3 O20 86.6(9) 2_666 . ?
O17 Cl3 O20 93.4(9) . . ?
O18 Cl3 O20 131.9(12) . 2_666 ?
O18 Cl3 O20 48.1(12) 2_666 2_666 ?
O18A Cl3 O20 41.2(19) 2_666 2_666 ?
O18A Cl3 O20 138.8(19) . 2_666 ?
O17 Cl3 O20 93.4(9) 2_666 2_666 ?
O17 Cl3 O20 86.6(9) . 2_666 ?
O20 Cl3 O20 180.0(13) . 2_666 ?
O18 Cl3 O19 99.9(11) . 2_666 ?
O18 Cl3 O19 80.1(11) 2_666 2_666 ?
O18A Cl3 O19 121(2) 2_666 2_666 ?
O18A Cl3 O19 59(2) . 2_666 ?
O17 Cl3 O19 87.3(7) 2_666 2_666 ?
O17 Cl3 O19 92.7(7) . 2_666 ?
O20 Cl3 O19 93.5(8) . 2_666 ?
O20 Cl3 O19 86.5(8) 2_666 2_666 ?
O18 Cl3 O19 80.1(11) . . ?
O18 Cl3 O19 99.9(11) 2_666 . ?
O18A Cl3 O19 59(2) 2_666 . ?
O18A Cl3 O19 121(2) . . ?
O17 Cl3 O19 92.7(7) 2_666 . ?
O17 Cl3 O19 87.3(7) . . ?
O20 Cl3 O19 86.5(8) . . ?
O20 Cl3 O19 93.5(8) 2_666 . ?
O19 Cl3 O19 180.000(3) 2_666 . ?
Cl4 Cl4 O24A 70.5(11) 2_775 . ?
Cl4 Cl4 O22A 81.0(18) 2_775 . ?
O24A Cl4 O22A 125.0(19) . . ?
Cl4 Cl4 O24A 55.4(8) 2_775 2_775 ?
O24A Cl4 O24A 125.8(9) . 2_775 ?
O22A Cl4 O24A 50.6(18) . 2_775 ?
Cl4 Cl4 O21 101.7(12) 2_775 . ?
O24A Cl4 O21 31.6(13) . . ?
O22A Cl4 O21 128(2) . . ?
O24A Cl4 O21 156.5(14) 2_775 . ?
Cl4 Cl4 O24 153(2) 2_775 . ?
O24A Cl4 O24 131(3) . . ?
O22A Cl4 O24 73(3) . . ?
O24A Cl4 O24 101(2) 2_775 . ?
O21 Cl4 O24 100(3) . . ?
Cl4 Cl4 O22 112.8(9) 2_775 . ?
O24A Cl4 O22 112.0(12) . . ?
O22A Cl4 O22 40.6(17) . . ?
O24A Cl4 O22 90.4(11) 2_775 . ?
O21 Cl4 O22 95.5(13) . . ?
O24 Cl4 O22 49(2) . . ?
Cl4 Cl4 O23 133.0(7) 2_775 . ?
O24A Cl4 O23 116.9(11) . . ?
O22A Cl4 O23 117.0(17) . . ?
O24A Cl4 O23 101.1(10) 2_775 . ?
O21 Cl4 O23 99.0(12) . . ?
O24 Cl4 O23 58(2) . . ?
O22 Cl4 O23 106.6(9) . . ?
Cl4 Cl4 O22A 50.9(13) 2_775 2_775 ?
O24A Cl4 O22A 45.4(15) . 2_775 ?
O22A Cl4 O22A 131.9(13) . 2_775 ?
O24A Cl4 O22A 94.1(15) 2_775 2_775 ?
O21 Cl4 O22A 70.8(17) . 2_775 ?
O24 Cl4 O22A 154(3) . 2_775 ?
O22 Cl4 O22A 152.6(16) . 2_775 ?
O23 Cl4 O22A 99.1(14) . 2_775 ?
Cl4 Cl4 O21 42.8(7) 2_775 2_775 ?
O24A Cl4 O21 113.1(11) . 2_775 ?
O22A Cl4 O21 58.8(19) . 2_775 ?
O24A Cl4 O21 13.2(10) 2_775 2_775 ?
O21 Cl4 O21 144.5(6) . 2_775 ?
O24 Cl4 O21 114(2) . 2_775 ?
O22 Cl4 O21 99.4(11) . 2_775 ?
O23 Cl4 O21 107.2(9) . 2_775 ?
O22A Cl4 O21 81.6(15) 2_775 2_775 ?
C10 O2 C11A 112.6(10) . . ?
C10 O2 C11 120.0(10) . . ?
C11A O2 C11 18.1(12) . . ?
C21 O3 C22 115.6(5) . . ?
C32 O5 Cu1 121.4(3) . . ?
C32 O6 Cu2 130.6(3) . . ?
C42 O7 C43 116.0(5) . . ?
O18 O17 Cl3 55.3(15) 2_666 . ?
O17 O18 Cl3 84.4(19) 2_666 . ?
Cl3 O18A O19 73(2) . 2_666 ?
O18A O19 Cl3 48.5(18) 2_666 . ?
Cl4 O21 Cl4 35.5(6) . 2_775 ?
O24A O22A Cl4 71(2) 2_775 . ?
O24A O22A Cl4 49.6(18) 2_775 2_775 ?
Cl4 O22A Cl4 48.1(13) . 2_775 ?
O22A O24A Cl4 85(2) 2_775 . ?
O22A O24A Cl4 58(2) 2_775 2_775 ?
Cl4 O24A Cl4 54.2(9) . 2_775 ?
C44A O25 C44 40.3(11) . . ?
C3 N1 N2 105.3(4) . . ?
C3 N1 Cu1 112.5(3) . . ?
N2 N1 Cu1 141.7(4) . . ?
C1 N2 N1 110.1(5) . . ?
C1 N2 C9 128.0(5) . . ?
N1 N2 C9 121.9(5) . . ?
C8 N3 C4 118.9(4) . . ?
C8 N3 Cu1 124.5(3) . . ?
C4 N3 Cu1 116.5(3) . . ?
C14 N4 N5 105.6(4) . . ?
C14 N4 Cu1 110.1(3) . . ?
N5 N4 Cu1 143.5(3) . . ?
N4 N5 C12 110.9(5) . . ?
N4 N5 C20 120.6(4) . . ?
C12 N5 C20 128.3(5) . . ?
C19 N6 C15 118.6(4) . . ?
C19 N6 Cu1 123.7(3) . . ?
C15 N6 Cu1 117.2(3) . . ?
C35 N7 N8 105.7(4) . . ?
C35 N7 Cu2 110.0(3) . . ?
N8 N7 Cu2 143.8(3) . . ?
N7 N8 C33 111.4(4) . . ?
N7 N8 C41 119.3(4) . . ?
C33 N8 C41 128.9(4) . . ?
C40 N9 C36 118.9(4) . . ?
C40 N9 Cu2 122.7(3) . . ?
C36 N9 Cu2 117.5(3) . . ?
C25 N10 N11 107.8(4) . . ?
C25 N10 Cu2 118.6(3) . . ?
N11 N10 Cu2 131.9(3) . . ?
C23 N11 N10 109.5(4) . . ?
C23 N11 C31 128.5(4) . . ?
N10 N11 C31 122.0(3) . . ?
C30 N12 C26 118.1(4) . . ?
C30 N12 Cu2 128.2(3) . . ?
C26 N12 Cu2 113.6(3) . . ?
C2 C1 N2 109.2(6) . . ?
C2 C1 H1 125.4 . . ?
N2 C1 H1 125.4 . . ?
C1 C2 C3 104.2(6) . . ?
C1 C2 H2 127.9 . . ?
C3 C2 H2 127.9 . . ?
N1 C3 C2 111.2(5) . . ?
N1 C3 C4 117.1(4) . . ?
C2 C3 C4 131.6(5) . . ?
N3 C4 C5 121.2(5) . . ?
N3 C4 C3 114.1(4) . . ?
C5 C4 C3 124.8(5) . . ?
C6 C5 C4 118.8(5) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C7 C6 C5 120.3(5) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 118.1(6) . . ?
C6 C7 H7 121.0 . . ?
C8 C7 H7 121.0 . . ?
N3 C8 C7 122.7(5) . . ?
N3 C8 H8 118.6 . . ?
C7 C8 H8 118.6 . . ?
N2 C9 C10 113.6(5) . . ?
N2 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
N2 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
O1 C10 O2 124.8(7) . . ?
O1 C10 C9 126.0(7) . . ?
O2 C10 C9 109.2(5) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
O2 C11A H11D 109.5 . . ?
O2 C11A H11E 109.5 . . ?
H11D C11A H11E 109.5 . . ?
O2 C11A H11F 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
N5 C12 C13 108.5(5) . . ?
N5 C12 H12 125.7 . . ?
C13 C12 H12 125.7 . . ?
C12 C13 C14 104.2(5) . . ?
C12 C13 H13 127.9 . . ?
C14 C13 H13 127.9 . . ?
N4 C14 C13 110.7(5) . . ?
N4 C14 C15 118.2(4) . . ?
C13 C14 C15 131.0(5) . . ?
N6 C15 C16 121.5(5) . . ?
N6 C15 C14 114.8(4) . . ?
C16 C15 C14 123.7(5) . . ?
C17 C16 C15 119.3(5) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 119.4(5) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C19 C18 C17 118.7(5) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
N6 C19 C18 122.4(5) . . ?
N6 C19 H19 118.8 . . ?
C18 C19 H19 118.8 . . ?
N5 C20 C21 111.5(4) . . ?
N5 C20 H20A 109.3 . . ?
C21 C20 H20A 109.3 . . ?
N5 C20 H20B 109.3 . . ?
C21 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
O4 C21 O3 126.0(5) . . ?
O4 C21 C20 125.1(5) . . ?
O3 C21 C20 109.0(4) . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N11 C23 C24 108.0(4) . . ?
N11 C23 H23 126.0 . . ?
C24 C23 H23 126.0 . . ?
C25 C24 C23 104.4(5) . . ?
C25 C24 H24 127.8 . . ?
C23 C24 H24 127.8 . . ?
N10 C25 C24 110.3(4) . . ?
N10 C25 C26 114.8(4) . . ?
C24 C25 C26 134.6(4) . . ?
N12 C26 C27 122.3(4) . . ?
N12 C26 C25 113.2(4) . . ?
C27 C26 C25 124.5(4) . . ?
C26 C27 C28 118.6(5) . . ?
C26 C27 H27 120.7 . . ?
C28 C27 H27 120.7 . . ?
C29 C28 C27 119.3(5) . . ?
C29 C28 H28 120.3 . . ?
C27 C28 H28 120.3 . . ?
C28 C29 C30 119.2(5) . . ?
C28 C29 H29 120.4 . . ?
C30 C29 H29 120.4 . . ?
N12 C30 C29 122.3(5) . . ?
N12 C30 H30 118.8 . . ?
C29 C30 H30 118.8 . . ?
N11 C31 C32 116.0(3) . . ?
N11 C31 H31A 108.3 . . ?
C32 C31 H31A 108.3 . . ?
N11 C31 H31B 108.3 . . ?
C32 C31 H31B 108.3 . . ?
H31A C31 H31B 107.4 . . ?
O6 C32 O5 123.7(4) . . ?
O6 C32 C31 123.6(4) . . ?
O5 C32 C31 112.6(4) . . ?
N8 C33 C34 107.3(4) . . ?
N8 C33 H33 126.4 . . ?
C34 C33 H33 126.4 . . ?
C33 C34 C35 105.1(4) . . ?
C33 C34 H34 127.5 . . ?
C35 C34 H34 127.5 . . ?
N7 C35 C34 110.6(4) . . ?
N7 C35 C36 117.4(4) . . ?
C34 C35 C36 132.0(4) . . ?
N9 C36 C37 121.2(5) . . ?
N9 C36 C35 115.7(4) . . ?
C37 C36 C35 123.1(4) . . ?
C38 C37 C36 119.1(5) . . ?
C38 C37 H37 120.5 . . ?
C36 C37 H37 120.5 . . ?
C39 C38 C37 119.6(5) . . ?
C39 C38 H38 120.2 . . ?
C37 C38 H38 120.2 . . ?
C38 C39 C40 119.2(5) . . ?
C38 C39 H39 120.4 . . ?
C40 C39 H39 120.4 . . ?
N9 C40 C39 121.9(5) . . ?
N9 C40 H40 119.0 . . ?
C39 C40 H40 119.0 . . ?
N8 C41 C42 111.3(4) . . ?
N8 C41 H41A 109.4 . . ?
C42 C41 H41A 109.4 . . ?
N8 C41 H41B 109.4 . . ?
C42 C41 H41B 109.4 . . ?
H41A C41 H41B 108.0 . . ?
O8 C42 O7 124.5(6) . . ?
O8 C42 C41 125.3(5) . . ?
O7 C42 C41 110.1(5) . . ?
O7 C43 H43A 109.5 . . ?
O7 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
O7 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C44A C44 O25 52.0(15) . . ?
C44 C44A O25 87.7(19) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.07
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         2.856
_refine_diff_density_min         -1.468
_refine_diff_density_rms         0.131
_database_code_depnum_ccdc_archive 'CCDC 1021993'
#######################################################################
#
#                 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_5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 Cl Cu N3 O2'
_chemical_formula_sum            'C10 H8 Cl Cu N3 O2'
_chemical_formula_weight         301.18

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'
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'

_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                   9.1736(5)
_cell_length_b                   6.8909(4)
_cell_length_c                   16.9201(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.292(2)
_cell_angle_gamma                90.00
_cell_volume                     1040.94(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9312
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      27.51

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.922
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             604
_exptl_absorpt_coefficient_mu    2.345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4941
_exptl_absorpt_correction_T_max  0.7993
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16640
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         27.55
_reflns_number_total             2384
_reflns_number_gt                2079
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_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)+(0.0257P)²+0.8760P] 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         2384
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0245
_refine_ls_wR_factor_ref         0.0613
_refine_ls_wR_factor_gt          0.0584
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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 0.34932(2) 0.18003(3) 0.127612(14) 0.01277(8) Uani 1 1 d . . .
Cl1 Cl 0.13629(5) 0.03947(8) 0.14091(3) 0.02061(12) Uani 1 1 d . . .
O1 O 0.47509(15) 0.0316(2) 0.21985(9) 0.0195(3) Uani 1 1 d . . .
O2 O 0.67933(17) -0.0405(2) 0.31388(9) 0.0258(4) Uani 1 1 d . . .
N1 N 0.52877(17) 0.2229(2) 0.08822(10) 0.0138(3) Uani 1 1 d . . .
N2 N 0.67149(18) 0.1744(2) 0.11978(10) 0.0149(3) Uani 1 1 d . . .
N3 N 0.26077(18) 0.2772(2) 0.01113(10) 0.0147(3) Uani 1 1 d . . .
C1 C 0.7503(2) 0.1772(3) 0.06119(14) 0.0194(4) Uani 1 1 d . . .
H1 H 0.8540 0.1493 0.0686 0.023 Uiso 1 1 calc R . .
C2 C 0.6540(2) 0.2275(3) -0.01080(13) 0.0193(4) Uani 1 1 d . . .
H2 H 0.6768 0.2420 -0.0625 0.023 Uiso 1 1 calc R . .
C3 C 0.5155(2) 0.2525(3) 0.00861(12) 0.0143(4) Uani 1 1 d . . .
C4 C 0.3615(2) 0.2932(3) -0.03597(12) 0.0149(4) Uani 1 1 d . . .
C5 C 0.3191(3) 0.3422(3) -0.11740(13) 0.0210(5) Uani 1 1 d . . .
H5 H 0.3910 0.3500 -0.1497 0.025 Uiso 1 1 calc R . .
C6 C 0.1689(3) 0.3796(3) -0.15053(13) 0.0256(5) Uani 1 1 d . . .
H6 H 0.1363 0.4124 -0.2063 0.031 Uiso 1 1 calc R . .
C7 C 0.0671(3) 0.3689(3) -0.10224(14) 0.0263(5) Uani 1 1 d . . .
H7 H -0.0356 0.3983 -0.1239 0.032 Uiso 1 1 calc R . .
C8 C 0.1164(2) 0.3150(3) -0.02190(13) 0.0203(4) Uani 1 1 d . . .
H8 H 0.0456 0.3043 0.0110 0.024 Uiso 1 1 calc R . .
C9 C 0.7225(2) 0.1462(3) 0.20714(12) 0.0190(4) Uani 1 1 d . . .
H9A H 0.7420 0.2753 0.2331 0.023 Uiso 1 1 calc R . .
H9B H 0.8190 0.0756 0.2176 0.023 Uiso 1 1 calc R . .
C10 C 0.6154(2) 0.0353(3) 0.24892(12) 0.0172(4) Uani 1 1 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 N1 1.9355(16) . ?
Cu1 O1 1.9962(14) . ?
Cu1 N3 2.0632(16) . ?
Cu1 O2 2.2083(15) 2_655 ?
Cu1 Cl1 2.2383(5) . ?
O1 C10 1.269(2) . ?
O2 C10 1.236(2) . ?
O2 Cu1 2.2083(15) 2_645 ?
N1 N2 1.338(2) . ?
N1 C3 1.340(3) . ?
N2 C1 1.355(3) . ?
N2 C9 1.457(3) . ?
N3 C8 1.339(3) . ?
N3 C4 1.356(3) . ?
C1 C2 1.375(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.394(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.468(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.377(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.539(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?

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 O1 87.88(6) . . ?
N1 Cu1 N3 78.51(7) . . ?
O1 Cu1 N3 160.57(6) . . ?
N1 Cu1 O2 102.68(6) . 2_655 ?
O1 Cu1 O2 101.72(6) . 2_655 ?
N3 Cu1 O2 94.81(6) . 2_655 ?
N1 Cu1 Cl1 158.76(5) . . ?
O1 Cu1 Cl1 93.48(4) . . ?
N3 Cu1 Cl1 94.33(5) . . ?
O2 Cu1 Cl1 97.80(5) 2_655 . ?
C10 O1 Cu1 130.21(13) . . ?
C10 O2 Cu1 133.33(14) . 2_645 ?
N2 N1 C3 107.08(16) . . ?
N2 N1 Cu1 131.01(13) . . ?
C3 N1 Cu1 118.77(13) . . ?
N1 N2 C1 110.02(17) . . ?
N1 N2 C9 119.64(16) . . ?
C1 N2 C9 130.04(17) . . ?
C8 N3 C4 118.74(18) . . ?
C8 N3 Cu1 126.59(14) . . ?
C4 N3 Cu1 114.58(13) . . ?
N2 C1 C2 108.04(18) . . ?
N2 C1 H1 126.0 . . ?
C2 C1 H1 126.0 . . ?
C1 C2 C3 104.91(18) . . ?
C1 C2 H2 127.5 . . ?
C3 C2 H2 127.5 . . ?
N1 C3 C2 109.93(18) . . ?
N1 C3 C4 113.59(17) . . ?
C2 C3 C4 136.41(18) . . ?
N3 C4 C5 122.10(19) . . ?
N3 C4 C3 112.81(17) . . ?
C5 C4 C3 125.09(19) . . ?
C4 C5 C6 118.2(2) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C7 C6 C5 119.8(2) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 119.0(2) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
N3 C8 C7 122.1(2) . . ?
N3 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
N2 C9 C10 116.26(16) . . ?
N2 C9 H9A 108.2 . . ?
C10 C9 H9A 108.2 . . ?
N2 C9 H9B 108.2 . . ?
C10 C9 H9B 108.2 . . ?
H9A C9 H9B 107.4 . . ?
O2 C10 O1 124.59(19) . . ?
O2 C10 C9 113.34(17) . . ?
O1 C10 C9 122.00(18) . . ?

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
N1 Cu1 O1 C10 20.79(18) . . . . ?
N3 Cu1 O1 C10 66.0(3) . . . . ?
O2 Cu1 O1 C10 -81.72(18) 2_655 . . . ?
Cl1 Cu1 O1 C10 179.57(17) . . . . ?
O1 Cu1 N1 N2 -3.61(17) . . . . ?
N3 Cu1 N1 N2 -169.66(18) . . . . ?
O2 Cu1 N1 N2 97.93(17) 2_655 . . . ?
Cl1 Cu1 N1 N2 -97.8(2) . . . . ?
O1 Cu1 N1 C3 153.55(15) . . . . ?
N3 Cu1 N1 C3 -12.50(14) . . . . ?
O2 Cu1 N1 C3 -104.91(15) 2_655 . . . ?
Cl1 Cu1 N1 C3 59.4(2) . . . . ?
C3 N1 N2 C1 1.4(2) . . . . ?
Cu1 N1 N2 C1 160.60(14) . . . . ?
C3 N1 N2 C9 175.80(17) . . . . ?
Cu1 N1 N2 C9 -25.0(3) . . . . ?
N1 Cu1 N3 C8 -174.48(18) . . . . ?
O1 Cu1 N3 C8 139.13(19) . . . . ?
O2 Cu1 N3 C8 -72.50(17) 2_655 . . . ?
Cl1 Cu1 N3 C8 25.71(16) . . . . ?
N1 Cu1 N3 C4 9.03(13) . . . . ?
O1 Cu1 N3 C4 -37.4(3) . . . . ?
O2 Cu1 N3 C4 111.02(13) 2_655 . . . ?
Cl1 Cu1 N3 C4 -150.77(12) . . . . ?
N1 N2 C1 C2 -0.7(2) . . . . ?
C9 N2 C1 C2 -174.24(19) . . . . ?
N2 C1 C2 C3 -0.4(2) . . . . ?
N2 N1 C3 C2 -1.7(2) . . . . ?
Cu1 N1 C3 C2 -163.85(13) . . . . ?
N2 N1 C3 C4 175.73(16) . . . . ?
Cu1 N1 C3 C4 13.6(2) . . . . ?
C1 C2 C3 N1 1.3(2) . . . . ?
C1 C2 C3 C4 -175.3(2) . . . . ?
C8 N3 C4 C5 -1.7(3) . . . . ?
Cu1 N3 C4 C5 175.03(14) . . . . ?
C8 N3 C4 C3 178.55(17) . . . . ?
Cu1 N3 C4 C3 -4.7(2) . . . . ?
N1 C3 C4 N3 -5.1(2) . . . . ?
C2 C3 C4 N3 171.4(2) . . . . ?
N1 C3 C4 C5 175.21(18) . . . . ?
C2 C3 C4 C5 -8.3(4) . . . . ?
N3 C4 C5 C6 1.4(3) . . . . ?
C3 C4 C5 C6 -178.97(19) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C5 C6 C7 C8 -2.0(3) . . . . ?
C4 N3 C8 C7 0.2(3) . . . . ?
Cu1 N3 C8 C7 -176.15(15) . . . . ?
C6 C7 C8 N3 1.7(3) . . . . ?
N1 N2 C9 C10 41.8(2) . . . . ?
C1 N2 C9 C10 -145.1(2) . . . . ?
Cu1 O2 C10 O1 41.6(3) 2_645 . . . ?
Cu1 O2 C10 C9 -141.33(16) 2_645 . . . ?
Cu1 O1 C10 O2 168.37(16) . . . . ?
Cu1 O1 C10 C9 -8.5(3) . . . . ?
N2 C9 C10 O2 157.16(18) . . . . ?
N2 C9 C10 O1 -25.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.077

#===END
_database_code_depnum_ccdc_archive 'CCDC 1021994'
