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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_nhjan202010_0m
_database_code_depnum_ccdc_archive 'CCDC 1020283'
_audit_update_record             
;
2014-08-20 deposited with the CCDC.
2014-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 N8 O2'
_chemical_formula_sum            'C20 H14 N8 O2'
_chemical_formula_weight         398.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.7883(5)
_cell_length_b                   15.5419(10)
_cell_length_c                   14.6518(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.984(3)
_cell_angle_gamma                90
_cell_volume                     1734.87(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9930
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      30.59

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6575
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   Bruker-SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18877
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.933
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3413
_reflns_number_gt                2982
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0618P)²+3.4031P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3413
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1105
_refine_ls_R_factor_gt           0.0954
_refine_ls_wR_factor_ref         0.2146
_refine_ls_wR_factor_gt          0.2013
_refine_ls_goodness_of_fit_ref   1.425
_refine_ls_restrained_S_all      1.425
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0099(5) 0.4990(2) 0.5497(2) 0.0128(8) Uani 1 1 d . . . . .
C2 C 0.0423(5) 0.4295(2) 0.6124(2) 0.0135(8) Uani 1 1 d . . . . .
C3 C 0.0118(5) 0.4381(2) 0.7029(2) 0.0158(8) Uani 1 1 d . . . . .
H3 H 0.0429 0.3935 0.7455 0.019 Uiso 1 1 calc R U . . .
C4 C -0.0628(5) 0.5108(3) 0.7297(3) 0.0196(9) Uani 1 1 d . . . . .
H4 H -0.0843 0.5158 0.7896 0.023 Uiso 1 1 calc R U . . .
C5 C -0.1055(5) 0.5766(3) 0.6661(3) 0.0179(8) Uani 1 1 d . . . . .
H5 H -0.1538 0.6269 0.6843 0.021 Uiso 1 1 calc R U . . .
C6 C 0.1810(5) 0.2854(2) 0.6327(2) 0.0156(8) Uani 1 1 d . . . . .
C7 C 0.2582(5) 0.2203(2) 0.5753(2) 0.0161(8) Uani 1 1 d . . . . .
C8 C 0.3336(5) 0.1456(3) 0.6173(3) 0.0191(9) Uani 1 1 d . . . . .
H8 H 0.3391 0.1375 0.6807 0.023 Uiso 1 1 calc R U . . .
C9 C 0.3858(5) 0.1010(3) 0.4785(3) 0.0226(9) Uani 1 1 d . . . . .
H9 H 0.4268 0.0602 0.4418 0.027 Uiso 1 1 calc R U . . .
C10 C 0.3133(5) 0.1765(3) 0.4372(3) 0.0214(9) Uani 1 1 d . . . . .
H10 H 0.3098 0.1852 0.3740 0.026 Uiso 1 1 calc R U . . .
C11 C 0.5024(4) -0.0109(2) 0.9505(2) 0.0129(8) Uani 1 1 d . . . . .
C12 C 0.5683(4) 0.0438(2) 0.8879(2) 0.0122(7) Uani 1 1 d . . . . .
C13 C 0.5644(5) 0.0139(2) 0.7976(2) 0.0154(8) Uani 1 1 d . . . . .
H13 H 0.6073 0.0480 0.7552 0.018 Uiso 1 1 calc R U . . .
C14 C 0.4965(5) -0.0663(3) 0.7717(2) 0.0177(8) Uani 1 1 d . . . . .
H14 H 0.4927 -0.0865 0.7116 0.021 Uiso 1 1 calc R U . . .
C15 C 0.4346(5) -0.1163(2) 0.8351(3) 0.0165(8) Uani 1 1 d . . . . .
H15 H 0.3888 -0.1704 0.8172 0.020 Uiso 1 1 calc R U . . .
C16 C 0.6995(5) 0.1864(3) 0.8694(3) 0.0178(8) Uani 1 1 d . . . . .
C17 C 0.7671(5) 0.2635(3) 0.9278(3) 0.0174(8) Uani 1 1 d . . . . .
C18 C 0.8437(5) 0.3306(3) 0.8883(3) 0.0244(10) Uani 1 1 d . . . . .
H18 H 0.8551 0.3256 0.8265 0.029 Uiso 1 1 calc R U . . .
C19 C 0.8814(5) 0.4044(3) 1.0235(3) 0.0255(9) Uani 1 1 d . . . . .
H19 H 0.9164 0.4534 1.0589 0.031 Uiso 1 1 calc R U . . .
C20 C 0.8099(5) 0.3360(3) 1.0643(3) 0.0229(9) Uani 1 1 d . . . . .
H20 H 0.8032 0.3399 1.1268 0.027 Uiso 1 1 calc R U . . .
N1 N -0.0798(4) 0.5703(2) 0.5795(2) 0.0170(7) Uani 1 1 d . . . . .
N2 N 0.1197(4) 0.3563(2) 0.5831(2) 0.0149(7) Uani 1 1 d . . . . .
N3 N 0.2485(4) 0.2372(2) 0.4850(2) 0.0196(7) Uani 1 1 d . . . . .
N4 N 0.3986(5) 0.0849(2) 0.5694(2) 0.0235(8) Uani 1 1 d . . . . .
N5 N 0.4386(4) -0.0888(2) 0.9218(2) 0.0162(7) Uani 1 1 d . . . . .
N6 N 0.6371(4) 0.1247(2) 0.9181(2) 0.0154(7) Uani 1 1 d . . . . .
N7 N 0.7510(4) 0.2657(2) 1.0170(2) 0.0205(7) Uani 1 1 d . . . . .
N8 N 0.9017(5) 0.4020(2) 0.9353(2) 0.0293(9) Uani 1 1 d . . . . .
O1 O 0.1797(4) 0.27037(18) 0.71440(18) 0.0234(7) Uani 1 1 d . . . . .
O2 O 0.7039(4) 0.18521(19) 0.78640(19) 0.0274(7) Uani 1 1 d . . . . .
H2 H 0.137(6) 0.358(3) 0.526(3) 0.025(12) Uiso 1 1 d . . . . .
H6 H 0.638(6) 0.137(3) 0.975(3) 0.020(11) Uiso 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
C1 N1 1.346(5) . ?
C1 C2 1.422(5) . ?
C1 C1 1.496(7) 3_566 ?
C2 N2 1.397(5) . ?
C2 C3 1.401(5) . ?
C3 C4 1.365(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(5) . ?
C4 H4 0.9300 . ?
C5 N1 1.329(5) . ?
C5 H5 0.9300 . ?
C6 O1 1.222(4) . ?
C6 N2 1.351(5) . ?
C6 C7 1.518(5) . ?
C7 N3 1.337(5) . ?
C7 C8 1.385(5) . ?
C8 N4 1.336(5) . ?
C8 H8 0.9300 . ?
C9 N4 1.339(5) . ?
C9 C10 1.385(6) . ?
C9 H9 0.9300 . ?
C10 N3 1.335(5) . ?
C10 H10 0.9300 . ?
C11 N5 1.343(5) . ?
C11 C12 1.421(5) . ?
C11 C11 1.499(7) 3_657 ?
C12 C13 1.396(5) . ?
C12 N6 1.402(5) . ?
C13 C14 1.376(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(5) . ?
C14 H14 0.9300 . ?
C15 N5 1.335(5) . ?
C15 H15 0.9300 . ?
C16 O2 1.223(5) . ?
C16 N6 1.346(5) . ?
C16 C17 1.502(6) . ?
C17 N7 1.339(5) . ?
C17 C18 1.387(5) . ?
C18 N8 1.335(5) . ?
C18 H18 0.9300 . ?
C19 N8 1.334(6) . ?
C19 C20 1.391(6) . ?
C19 H19 0.9300 . ?
C20 N7 1.325(5) . ?
C20 H20 0.9300 . ?
N2 H2 0.87(5) . ?
N6 H6 0.85(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 119.8(3) . . ?
N1 C1 C1 115.4(4) . 3_566 ?
C2 C1 C1 124.8(4) . 3_566 ?
N2 C2 C3 122.5(3) . . ?
N2 C2 C1 120.2(3) . . ?
C3 C2 C1 117.2(3) . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 118.6(3) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 121.9(4) . . ?
N1 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
O1 C6 N2 127.6(4) . . ?
O1 C6 C7 120.0(3) . . ?
N2 C6 C7 112.4(3) . . ?
N3 C7 C8 122.4(4) . . ?
N3 C7 C6 118.0(3) . . ?
C8 C7 C6 119.6(3) . . ?
N4 C8 C7 122.0(4) . . ?
N4 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
N4 C9 C10 122.2(4) . . ?
N4 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
N3 C10 C9 122.2(4) . . ?
N3 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
N5 C11 C12 119.8(3) . . ?
N5 C11 C11 115.1(4) . 3_657 ?
C12 C11 C11 125.1(4) . 3_657 ?
C13 C12 N6 121.9(3) . . ?
C13 C12 C11 118.2(3) . . ?
N6 C12 C11 119.8(3) . . ?
C14 C13 C12 119.5(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
N5 C15 C14 121.4(4) . . ?
N5 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
O2 C16 N6 127.1(4) . . ?
O2 C16 C17 120.0(3) . . ?
N6 C16 C17 112.8(3) . . ?
N7 C17 C18 121.6(4) . . ?
N7 C17 C16 119.0(3) . . ?
C18 C17 C16 119.4(3) . . ?
N8 C18 C17 122.6(4) . . ?
N8 C18 H18 118.7 . . ?
C17 C18 H18 118.7 . . ?
N8 C19 C20 122.3(4) . . ?
N8 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
N7 C20 C19 122.1(4) . . ?
N7 C20 H20 119.0 . . ?
C19 C20 H20 119.0 . . ?
C5 N1 C1 121.4(3) . . ?
C6 N2 C2 128.7(3) . . ?
C6 N2 H2 116(3) . . ?
C2 N2 H2 115(3) . . ?
C10 N3 C7 115.5(3) . . ?
C8 N4 C9 115.6(3) . . ?
C15 N5 C11 121.3(3) . . ?
C16 N6 C12 128.9(3) . . ?
C16 N6 H6 115(3) . . ?
C12 N6 H6 116(3) . . ?
C20 N7 C17 116.1(3) . . ?
C18 N8 C19 115.3(4) . . ?

_refine_diff_density_max         0.441
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.106

_shelxl_version_number           2013-3



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_nhjan
_database_code_depnum_ccdc_archive 'CCDC 1020284'
_audit_update_record             
;
2014-08-20 deposited with the CCDC.
2014-11-25 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT019_nhjan               
;
PROBLEM: _diffrn_measured_fraction_theta_full/_max < 1.0 0.973 Why ?
RESPONSE: A full dataset was collected but the crystal was quite weakly diffracting 
at high angles.
;
_vrf_PLAT341_nhjan               
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.0238 Ang.
RESPONSE:The crystal was quite weakly diffracting especially at high angles.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'2(C26 H21 Cl Cu3 N8 O8), 2(C H4 O), 2(H O0.50)'
_chemical_formula_sum            'C54 H52 Cl2 Cu6 N16 O19'
_chemical_formula_weight         1681.25

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.1126(16)
_cell_length_b                   12.3344(19)
_cell_length_c                   14.390(2)
_cell_angle_alpha                94.368(6)
_cell_angle_beta                 101.891(4)
_cell_angle_gamma                112.023(4)
_cell_volume                     1604.8(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6259
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      26.30

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    2.120
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6264
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   Bruker-SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6425
_diffrn_reflns_av_unetI/netI     0.0870
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.537
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.838
_diffrn_measured_fraction_theta_full 0.815
_diffrn_reflns_Laue_measured_fraction_max 0.838
_diffrn_reflns_Laue_measured_fraction_full 0.815
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_point_group_measured_fraction_full 0.815
_reflns_number_total             4726
_reflns_number_gt                3348
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0001P)²+53.7921P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4726
_refine_ls_number_parameters     448
_refine_ls_number_restraints     138
_refine_ls_R_factor_all          0.1607
_refine_ls_R_factor_gt           0.1096
_refine_ls_wR_factor_ref         0.2575
_refine_ls_wR_factor_gt          0.2180
_refine_ls_goodness_of_fit_ref   1.214
_refine_ls_restrained_S_all      1.202
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.4292(2) 0.54954(17) 0.44479(12) 0.0218(5) Uani 1 1 d . U . . .
Cu2 Cu 0.0474(2) 0.82190(19) 0.14164(13) 0.0277(5) Uani 1 1 d . U . . .
Cu3 Cu -0.1654(2) 0.97716(19) 0.22572(13) 0.0331(6) Uani 1 1 d . U . . .
Cl1 Cl 0.0865(6) 0.9952(5) 0.2497(4) 0.0611(14) Uani 1 1 d . U . . .
O1 O 0.6246(11) 0.6640(10) 0.4406(7) 0.032(2) Uani 1 1 d . U . . .
O2 O 0.4386(11) 0.4429(9) 0.3412(7) 0.028(2) Uani 1 1 d . U . . .
O3 O 0.4422(14) 0.6432(11) 0.5644(7) 0.041(3) Uani 1 1 d . U . . .
O4 O 0.2547(12) 0.4205(11) 0.4632(8) 0.037(3) Uani 1 1 d . U . . .
O5 O 0.4817(12) 0.8862(12) 0.1967(8) 0.042(3) Uani 1 1 d . U . . .
O6 O -0.1480(12) 0.7206(10) 0.1509(8) 0.034(2) Uani 1 1 d . U . . .
O7 O -0.2497(14) 0.8124(11) 0.2386(8) 0.040(3) Uani 1 1 d . U . . .
O8 O -0.1373(14) 1.3100(11) 0.2922(8) 0.043(3) Uani 1 1 d . U . . .
O10 O 0.777(2) 0.403(2) 0.1351(13) 0.094(6) Uani 1 1 d . U . . .
H10S H 0.8364 0.4088 0.1854 0.141 Uiso 1 1 calc R U . . .
O1S O 0.879(6) 0.501(4) 0.410(4) 0.134(16) Uiso 0.5 1 d D . P . .
H1S H 0.94(4) 0.48(4) 0.46(4) 0.201 Uiso 0.5 1 d D U P . .
H2S H 0.78(3) 0.44(3) 0.39(4) 0.201 Uiso 0.5 1 d D U P . .
N1 N 0.2964(14) 0.6238(12) 0.3513(9) 0.027(3) Uani 1 1 d . U . . .
N2 N 0.1336(15) 0.7239(13) 0.2363(9) 0.033(3) Uani 1 1 d . U . . .
N3 N 0.2456(14) 0.8777(13) 0.1269(8) 0.030(3) Uani 1 1 d . U . . .
N4 N -0.0206(13) 0.7957(13) -0.0077(9) 0.029(3) Uani 1 1 d . U . . .
N5 N -0.2471(14) 0.9573(12) 0.0756(8) 0.026(3) Uani 1 1 d . U . . .
N6 N -0.1174(14) 1.1429(12) 0.2244(8) 0.030(2) Uani 1 1 d . U . . .
N7 N -0.2321(13) 1.0189(13) 0.3456(9) 0.031(3) Uani 1 1 d . U . . .
N8 N -0.3287(18) 1.1040(15) 0.4897(12) 0.050(4) Uani 1 1 d . U . . .
C1 C 0.069(2) 0.6410(17) 0.2861(13) 0.044(5) Uani 1 1 d . U . . .
H1 H -0.0307 0.6169 0.2822 0.053 Uiso 1 1 calc R U . . .
C2 C 0.1510(19) 0.5901(16) 0.3439(11) 0.035(4) Uani 1 1 d . U . . .
H2 H 0.1043 0.5321 0.3777 0.042 Uiso 1 1 calc R U . . .
C3 C 0.3563(19) 0.7056(15) 0.3010(10) 0.033(4) Uani 1 1 d . U . . .
H3 H 0.4562 0.7297 0.3040 0.040 Uiso 1 1 calc R U . . .
C4 C 0.2762(17) 0.7575(15) 0.2436(10) 0.028(3) Uani 1 1 d . U . . .
C5 C 0.3481(17) 0.8486(16) 0.1865(10) 0.030(4) Uani 1 1 d . U . . .
C6 C 0.2964(16) 0.9663(15) 0.0721(10) 0.024(3) Uani 1 1 d . U . . .
C7 C 0.4282(17) 1.0635(15) 0.1041(11) 0.031(3) Uani 1 1 d . U . . .
H7 H 0.4905 1.0703 0.1636 0.037 Uiso 1 1 calc R U . . .
C8 C 0.469(2) 1.1510(15) 0.0490(11) 0.033(4) Uani 1 1 d . U . . .
H8 H 0.5570 1.2177 0.0710 0.039 Uiso 1 1 calc R U . . .
C9 C 0.0676(15) 0.8493(14) -0.0658(10) 0.020(3) Uani 1 1 d . U . . .
C10 C -0.1450(18) 0.6983(17) -0.0468(12) 0.038(4) Uani 1 1 d . U . . .
H10 H -0.2055 0.6636 -0.0073 0.045 Uiso 1 1 calc R U . . .
C11 C -0.1870(18) 0.6476(18) -0.1425(11) 0.040(4) Uani 1 1 d . U . . .
H11 H -0.2742 0.5807 -0.1671 0.048 Uiso 1 1 calc R U . . .
C12 C -0.2423(17) 0.7215(15) 0.1972(10) 0.028(3) Uani 1 1 d . U . . .
C13 C -0.358(2) 0.6032(16) 0.1966(14) 0.049(5) Uani 1 1 d . U . . .
H13A H -0.3182 0.5440 0.1933 0.074 Uiso 1 1 calc R U . . .
H13B H -0.4398 0.5846 0.1416 0.074 Uiso 1 1 calc R U . . .
H13C H -0.3912 0.6046 0.2544 0.074 Uiso 1 1 calc R U . . .
C14 C -0.3752(19) 0.8629(16) 0.0397(11) 0.032(4) Uani 1 1 d . U . . .
H14 H -0.4024 0.8036 0.0768 0.039 Uiso 1 1 calc R U . . .
C15 C -0.2049(15) 1.0452(14) 0.0212(9) 0.019(3) Uani 1 1 d . U . . .
C16 C 0.096(2) 1.3017(16) 0.2010(13) 0.042(4) Uani 1 1 d . U . . .
H16 H 0.1204 1.3351 0.2655 0.051 Uiso 1 1 calc R U . . .
C17 C -0.0299(19) 1.2008(15) 0.1625(11) 0.032(3) Uani 1 1 d . U . . .
C18 C -0.1531(19) 1.2063(16) 0.2861(11) 0.034(3) Uani 1 1 d . U . . .
C19 C -0.2226(18) 1.1326(16) 0.3553(11) 0.033(3) Uani 1 1 d . U . . .
C20 C -0.2715(19) 1.1749(17) 0.4276(13) 0.040(4) Uani 1 1 d . U . . .
H20 H -0.2652 1.2524 0.4337 0.048 Uiso 1 1 calc R U . . .
C21 C -0.332(2) 0.9979(19) 0.4800(16) 0.056(5) Uani 1 1 d . U . . .
H21 H -0.3669 0.9492 0.5235 0.067 Uiso 1 1 calc R U . . .
C22 C -0.286(2) 0.9541(17) 0.4073(14) 0.043(4) Uani 1 1 d . U . . .
H22 H -0.2931 0.8763 0.4023 0.051 Uiso 1 1 calc R U . . .
C23 C 0.7396(18) 0.6558(16) 0.4869(12) 0.035(4) Uani 1 1 d . U . . .
C24 C 0.8875(19) 0.7491(18) 0.4807(14) 0.051(5) Uani 1 1 d . U . . .
H24A H 0.8811 0.7635 0.4156 0.076 Uiso 1 1 calc R U . . .
H24B H 0.9636 0.7206 0.4998 0.076 Uiso 1 1 calc R U . . .
H24C H 0.9105 0.8215 0.5227 0.076 Uiso 1 1 calc R U . . .
C25 C 0.4942(18) 0.3701(15) 0.3554(11) 0.030(4) Uani 1 1 d . U . . .
C26 C 0.489(2) 0.291(2) 0.2698(13) 0.058(6) Uani 1 1 d . U . . .
H26A H 0.4552 0.3177 0.2122 0.086 Uiso 1 1 calc R U . . .
H26B H 0.4224 0.2113 0.2692 0.086 Uiso 1 1 calc R U . . .
H26C H 0.5857 0.2935 0.2729 0.086 Uiso 1 1 calc R U . . .
C27 C 0.849(3) 0.423(2) 0.0591(17) 0.077(7) Uani 1 1 d . U . . .
H27A H 0.9518 0.4725 0.0853 0.115 Uiso 1 1 calc R U . . .
H27B H 0.8054 0.4615 0.0144 0.115 Uiso 1 1 calc R U . . .
H27C H 0.8388 0.3484 0.0265 0.115 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O3 1.950(11) . ?
Cu1 O2 1.952(10) . ?
Cu1 O4 1.967(11) . ?
Cu1 O1 1.967(11) . ?
Cu1 N1 2.195(11) . ?
Cu1 Cu1 2.595(3) 2_666 ?
Cu2 N3 1.923(13) . ?
Cu2 O6 1.940(12) . ?
Cu2 N4 2.077(12) . ?
Cu2 N2 2.151(12) . ?
Cu2 Cl1 2.399(6) . ?
Cu3 N6 1.918(14) . ?
Cu3 O7 1.927(12) . ?
Cu3 N7 2.074(13) . ?
Cu3 N5 2.107(12) . ?
Cu3 Cl1 2.421(6) . ?
O1 C23 1.260(18) . ?
O2 C25 1.236(18) . ?
O3 C25 1.254(18) 2_666 ?
O4 C23 1.238(19) 2_666 ?
O5 C5 1.226(18) . ?
O6 C12 1.274(18) . ?
O7 C12 1.263(19) . ?
O8 C18 1.222(19) . ?
O10 C27 1.42(3) . ?
N1 C3 1.32(2) . ?
N1 C2 1.35(2) . ?
N2 C4 1.321(19) . ?
N2 C1 1.34(2) . ?
N3 C5 1.378(18) . ?
N3 C6 1.398(19) . ?
N4 C10 1.35(2) . ?
N4 C9 1.371(18) . ?
N5 C14 1.34(2) . ?
N5 C15 1.374(18) . ?
N6 C18 1.33(2) . ?
N6 C17 1.43(2) . ?
N7 C22 1.31(2) . ?
N7 C19 1.36(2) . ?
N8 C21 1.29(2) . ?
N8 C20 1.36(2) . ?
C1 C2 1.40(2) . ?
C3 C4 1.394(19) . ?
C4 C5 1.50(2) . ?
C6 C7 1.38(2) . ?
C6 C15 1.430(18) 2_575 ?
C7 C8 1.38(2) . ?
C8 C14 1.38(2) 2_575 ?
C9 C17 1.39(2) 2_575 ?
C9 C15 1.48(2) 2_575 ?
C10 C11 1.38(2) . ?
C11 C16 1.38(2) 2_575 ?
C12 C13 1.49(2) . ?
C14 C8 1.38(2) 2_575 ?
C15 C6 1.430(18) 2_575 ?
C15 C9 1.48(2) 2_575 ?
C16 C17 1.38(2) . ?
C16 C11 1.38(2) 2_575 ?
C17 C9 1.39(2) 2_575 ?
C18 C19 1.50(2) . ?
C19 C20 1.39(2) . ?
C21 C22 1.38(3) . ?
C23 O4 1.238(19) 2_666 ?
C23 C24 1.53(2) . ?
C25 O3 1.254(18) 2_666 ?
C25 C26 1.49(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
O3 Cu1 O2 169.0(4) . . ?
O3 Cu1 O4 89.5(5) . . ?
O2 Cu1 O4 89.7(5) . . ?
O3 Cu1 O1 90.3(5) . . ?
O2 Cu1 O1 88.4(5) . . ?
O4 Cu1 O1 169.3(4) . . ?
O3 Cu1 N1 95.2(4) . . ?
O2 Cu1 N1 95.9(4) . . ?
O4 Cu1 N1 93.1(5) . . ?
O1 Cu1 N1 97.5(5) . . ?
O3 Cu1 Cu1 85.2(3) . 2_666 ?
O2 Cu1 Cu1 83.7(3) . 2_666 ?
O4 Cu1 Cu1 83.2(3) . 2_666 ?
O1 Cu1 Cu1 86.1(3) . 2_666 ?
N1 Cu1 Cu1 176.3(4) . 2_666 ?
N3 Cu2 O6 163.0(5) . . ?
N3 Cu2 N4 86.6(5) . . ?
O6 Cu2 N4 92.0(5) . . ?
N3 Cu2 N2 80.3(5) . . ?
O6 Cu2 N2 87.9(5) . . ?
N4 Cu2 N2 131.0(5) . . ?
N3 Cu2 Cl1 95.5(4) . . ?
O6 Cu2 Cl1 99.0(4) . . ?
N4 Cu2 Cl1 125.9(4) . . ?
N2 Cu2 Cl1 102.4(4) . . ?
N6 Cu3 O7 167.0(5) . . ?
N6 Cu3 N7 80.3(6) . . ?
O7 Cu3 N7 88.8(5) . . ?
N6 Cu3 N5 84.8(5) . . ?
O7 Cu3 N5 98.3(5) . . ?
N7 Cu3 N5 135.0(5) . . ?
N6 Cu3 Cl1 94.7(4) . . ?
O7 Cu3 Cl1 96.6(4) . . ?
N7 Cu3 Cl1 117.8(4) . . ?
N5 Cu3 Cl1 105.5(4) . . ?
Cu2 Cl1 Cu3 99.7(2) . . ?
C23 O1 Cu1 120.2(11) . . ?
C25 O2 Cu1 123.4(10) . . ?
C25 O3 Cu1 121.3(10) 2_666 . ?
C23 O4 Cu1 124.0(10) 2_666 . ?
C12 O6 Cu2 139.5(12) . . ?
C12 O7 Cu3 131.7(11) . . ?
C3 N1 C2 116.9(13) . . ?
C3 N1 Cu1 121.3(10) . . ?
C2 N1 Cu1 121.8(10) . . ?
C4 N2 C1 118.6(13) . . ?
C4 N2 Cu2 109.7(10) . . ?
C1 N2 Cu2 131.7(11) . . ?
C5 N3 C6 118.0(13) . . ?
C5 N3 Cu2 119.2(10) . . ?
C6 N3 Cu2 121.5(9) . . ?
C10 N4 C9 119.0(13) . . ?
C10 N4 Cu2 114.4(10) . . ?
C9 N4 Cu2 124.4(10) . . ?
C14 N5 C15 118.8(12) . . ?
C14 N5 Cu3 113.5(10) . . ?
C15 N5 Cu3 125.1(10) . . ?
C18 N6 C17 119.6(14) . . ?
C18 N6 Cu3 120.9(12) . . ?
C17 N6 Cu3 119.2(10) . . ?
C22 N7 C19 117.5(15) . . ?
C22 N7 Cu3 131.0(13) . . ?
C19 N7 Cu3 111.3(10) . . ?
C21 N8 C20 117.6(16) . . ?
N2 C1 C2 120.8(16) . . ?
N1 C2 C1 120.9(16) . . ?
N1 C3 C4 122.7(16) . . ?
N2 C4 C3 120.2(15) . . ?
N2 C4 C5 118.8(12) . . ?
C3 C4 C5 121.0(14) . . ?
O5 C5 N3 129.2(15) . . ?
O5 C5 C4 119.7(13) . . ?
N3 C5 C4 111.1(13) . . ?
C7 C6 N3 123.4(13) . . ?
C7 C6 C15 118.9(14) . 2_575 ?
N3 C6 C15 117.7(14) . 2_575 ?
C6 C7 C8 120.8(14) . . ?
C7 C8 C14 118.1(17) . 2_575 ?
N4 C9 C17 119.4(15) . 2_575 ?
N4 C9 C15 118.2(12) . 2_575 ?
C17 C9 C15 122.3(14) 2_575 2_575 ?
N4 C10 C11 123.2(16) . . ?
C10 C11 C16 118.4(17) . 2_575 ?
O7 C12 O6 126.3(16) . . ?
O7 C12 C13 118.3(14) . . ?
O6 C12 C13 115.3(15) . . ?
N5 C14 C8 123.8(15) . 2_575 ?
N5 C15 C6 119.7(14) . 2_575 ?
N5 C15 C9 117.0(11) . 2_575 ?
C6 C15 C9 123.2(13) 2_575 2_575 ?
C17 C16 C11 119.1(17) . 2_575 ?
C16 C17 C9 120.9(16) . 2_575 ?
C16 C17 N6 119.2(14) . . ?
C9 C17 N6 119.8(15) 2_575 . ?
O8 C18 N6 129.5(17) . . ?
O8 C18 C19 119.6(15) . . ?
N6 C18 C19 111.0(15) . . ?
N7 C19 C20 120.0(16) . . ?
N7 C19 C18 116.0(14) . . ?
C20 C19 C18 123.9(16) . . ?
N8 C20 C19 120.6(17) . . ?
N8 C21 C22 122.4(18) . . ?
N7 C22 C21 121.8(18) . . ?
O4 C23 O1 126.4(16) 2_666 . ?
O4 C23 C24 116.6(14) 2_666 . ?
O1 C23 C24 117.0(15) . . ?
O2 C25 O3 126.3(14) . 2_666 ?
O2 C25 C26 117.7(14) . . ?
O3 C25 C26 116.0(14) 2_666 . ?

_refine_diff_density_max         1.163
_refine_diff_density_min         -0.777
_refine_diff_density_rms         0.190

_shelxl_version_number           2013-3



