# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1462845'
_audit_update_record             
;
2016-11-16 deposited with the CCDC.
2016-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H16 Cu N6 O10'
_chemical_formula_sum            'C24 H16 Cu N6 O10'
_chemical_formula_weight         611.97

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'

_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                   7.3858(4)
_cell_length_b                   7.9511(4)
_cell_length_c                   9.9894(5)
_cell_angle_alpha                75.700(2)
_cell_angle_beta                 78.644(2)
_cell_angle_gamma                84.546(2)
_cell_volume                     556.66(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1450
_cell_measurement_theta_min      2.139
_cell_measurement_theta_max      28.284

_exptl_crystal_description       block
_exptl_crystal_colour            'Pale blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_F_000             311
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .3
_exptl_absorpt_coefficient_mu    1.061
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .701
_exptl_absorpt_correction_T_max  .731
_exptl_absorpt_process_details   'SADABS; (sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'INCOATEC Imus micro-focus source'
_diffrn_radiation_monochromator  mirrors
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12175
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.139
_diffrn_reflns_theta_max         28.284
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2745
_reflns_number_gt                2283
_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      'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Siemens)'
_computing_publication_material  SHELXL-97
_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)+(0.0409P)²+0.2157P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2745
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0871
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
Cu1 Cu 0.0000 0.0000 0.5000 0.02641(13) Uani 1 2 d S . P . .
O1 O 0.1854(2) 0.56080(19) 0.38188(16) 0.0393(4) Uani 1 1 d . . . . .
O2 O 0.0579(2) 0.06891(18) 0.27631(16) 0.0351(4) Uani 1 1 d . . . . .
O3 O 0.2509(2) -0.1546(2) 0.53544(17) 0.0446(4) Uani 1 1 d . . . . .
O4 O 0.5282(2) -0.2649(2) 0.4888(2) 0.0520(5) Uani 1 1 d . . . . .
O5 O 0.4339(3) -0.0389(3) 0.3449(2) 0.0648(6) Uani 1 1 d . . . . .
N1 N 0.1422(2) 0.3123(2) 0.32359(17) 0.0273(4) Uani 1 1 d . . . . .
N2 N 0.1057(3) 0.2292(2) 0.46950(18) 0.0285(4) Uani 1 1 d . . . . .
H1A H 0.029(3) 0.294(3) 0.503(3) 0.034 Uiso 1 1 d . U . . .
H1B H 0.211(4) 0.223(3) 0.495(2) 0.034 Uiso 1 1 d . U . . .
N3 N 0.4069(3) -0.1515(2) 0.4536(2) 0.0374(4) Uani 1 1 d . . . . .
C1 C 0.1905(3) 0.4876(3) 0.2883(2) 0.0280(4) Uani 1 1 d . . . . .
C2 C 0.2437(3) 0.5643(3) 0.1383(2) 0.0275(4) Uani 1 1 d . . . . .
C3 C 0.3083(3) 0.7302(3) 0.0949(2) 0.0325(5) Uani 1 1 d . . . . .
H3A H 0.3152 0.7931 0.1607 0.039 Uiso 1 1 calc R U . . .
C4 C 0.3631(3) 0.8031(3) -0.0487(2) 0.0366(5) Uani 1 1 d . . . . .
H4A H 0.4080 0.9141 -0.0777 0.044 Uiso 1 1 calc R U . . .
C5 C 0.3515(3) 0.7127(3) -0.1472(2) 0.0362(5) Uani 1 1 d . . . . .
H5A H 0.3876 0.7637 -0.2420 0.043 Uiso 1 1 calc R U . . .
C6 C 0.2856(3) 0.5435(3) -0.1063(2) 0.0316(5) Uani 1 1 d . . . . .
C7 C 0.2755(3) 0.4446(3) -0.2049(2) 0.0386(5) Uani 1 1 d . . . . .
H7A H 0.3125 0.4916 -0.3004 0.046 Uiso 1 1 calc R U . . .
C8 C 0.2114(3) 0.2804(3) -0.1598(2) 0.0409(6) Uani 1 1 d . . . . .
H8A H 0.2045 0.2172 -0.2254 0.049 Uiso 1 1 calc R U . . .
C9 C 0.1563(3) 0.2062(3) -0.0170(2) 0.0343(5) Uani 1 1 d . . . . .
H9A H 0.1120 0.0949 0.0116 0.041 Uiso 1 1 calc R U . . .
C10 C 0.1674(3) 0.2977(3) 0.0819(2) 0.0275(4) Uani 1 1 d . . . . .
C11 C 0.2317(3) 0.4679(2) 0.0391(2) 0.0263(4) Uani 1 1 d . . . . .
C12 C 0.1179(3) 0.2154(3) 0.2311(2) 0.0271(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 N2 1.9814(18) 2_556 ?
Cu1 N2 1.9814(18) . ?
Cu1 O2 2.1307(15) . ?
Cu1 O2 2.1307(15) 2_556 ?
Cu1 O3 2.1632(17) . ?
Cu1 O3 2.1632(17) 2_556 ?
O1 C1 1.211(3) . ?
O2 C12 1.231(2) . ?
O3 N3 1.273(2) . ?
O4 N3 1.246(3) . ?
O5 N3 1.220(2) . ?
N1 C12 1.387(3) . ?
N1 C1 1.413(2) . ?
N1 N2 1.427(2) . ?
N2 H1A 0.81(3) . ?
N2 H1B 0.85(3) . ?
C1 C2 1.461(3) . ?
C2 C3 1.382(3) . ?
C2 C11 1.414(3) . ?
C3 C4 1.401(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.374(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.409(3) . ?
C5 H5A 0.9300 . ?
C6 C11 1.420(3) . ?
C6 C7 1.420(3) . ?
C7 C8 1.369(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.397(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.383(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.413(3) . ?
C10 C12 1.461(3) . ?

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
N2 Cu1 N2 180.0 2_556 . ?
N2 Cu1 O2 99.70(6) 2_556 . ?
N2 Cu1 O2 80.30(6) . . ?
N2 Cu1 O2 80.30(6) 2_556 2_556 ?
N2 Cu1 O2 99.70(6) . 2_556 ?
O2 Cu1 O2 180.0 . 2_556 ?
N2 Cu1 O3 83.62(8) 2_556 . ?
N2 Cu1 O3 96.38(8) . . ?
O2 Cu1 O3 98.55(6) . . ?
O2 Cu1 O3 81.45(6) 2_556 . ?
N2 Cu1 O3 96.38(8) 2_556 2_556 ?
N2 Cu1 O3 83.62(8) . 2_556 ?
O2 Cu1 O3 81.45(6) . 2_556 ?
O2 Cu1 O3 98.55(6) 2_556 2_556 ?
O3 Cu1 O3 180.0 . 2_556 ?
C12 O2 Cu1 111.68(13) . . ?
N3 O3 Cu1 128.58(14) . . ?
C12 N1 C1 126.51(17) . . ?
C12 N1 N2 116.61(15) . . ?
C1 N1 N2 116.80(16) . . ?
N1 N2 Cu1 110.89(12) . . ?
N1 N2 H1A 103.8(17) . . ?
Cu1 N2 H1A 109.2(17) . . ?
N1 N2 H1B 103.8(16) . . ?
Cu1 N2 H1B 113.9(16) . . ?
H1A N2 H1B 115(2) . . ?
O5 N3 O4 122.1(2) . . ?
O5 N3 O3 119.8(2) . . ?
O4 N3 O3 118.06(19) . . ?
O1 C1 N1 118.73(18) . . ?
O1 C1 C2 125.71(18) . . ?
N1 C1 C2 115.56(17) . . ?
C3 C2 C11 120.65(19) . . ?
C3 C2 C1 119.37(19) . . ?
C11 C2 C1 119.97(17) . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C5 C6 C11 118.7(2) . . ?
C5 C6 C7 122.4(2) . . ?
C11 C6 C7 118.88(19) . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
C7 C8 C9 121.1(2) . . ?
C7 C8 H8A 119.5 . . ?
C9 C8 H8A 119.5 . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
C9 C10 C11 120.24(19) . . ?
C9 C10 C12 119.58(19) . . ?
C11 C10 C12 120.15(19) . . ?
C10 C11 C2 121.27(18) . . ?
C10 C11 C6 119.38(19) . . ?
C2 C11 C6 119.35(18) . . ?
O2 C12 N1 120.14(18) . . ?
O2 C12 C10 123.82(19) . . ?
N1 C12 C10 116.04(17) . . ?

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
C12 N1 N2 Cu1 -6.6(2) . . . . ?
C1 N1 N2 Cu1 170.40(14) . . . . ?
Cu1 O3 N3 O5 7.9(3) . . . . ?
Cu1 O3 N3 O4 -172.45(15) . . . . ?
C12 N1 C1 O1 171.4(2) . . . . ?
N2 N1 C1 O1 -5.3(3) . . . . ?
C12 N1 C1 C2 -8.8(3) . . . . ?
N2 N1 C1 C2 174.52(17) . . . . ?
O1 C1 C2 C3 5.3(3) . . . . ?
N1 C1 C2 C3 -174.49(18) . . . . ?
O1 C1 C2 C11 -175.7(2) . . . . ?
N1 C1 C2 C11 4.5(3) . . . . ?
C11 C2 C3 C4 -0.3(3) . . . . ?
C1 C2 C3 C4 178.68(19) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C11 -0.2(3) . . . . ?
C4 C5 C6 C7 -178.6(2) . . . . ?
C5 C6 C7 C8 179.6(2) . . . . ?
C11 C6 C7 C8 1.2(3) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C8 C9 C10 C12 -177.0(2) . . . . ?
C9 C10 C11 C2 179.80(19) . . . . ?
C12 C10 C11 C2 -2.2(3) . . . . ?
C9 C10 C11 C6 -0.3(3) . . . . ?
C12 C10 C11 C6 177.71(18) . . . . ?
C3 C2 C11 C10 179.49(19) . . . . ?
C1 C2 C11 C10 0.5(3) . . . . ?
C3 C2 C11 C6 -0.4(3) . . . . ?
C1 C2 C11 C6 -179.39(18) . . . . ?
C5 C6 C11 C10 -179.25(19) . . . . ?
C7 C6 C11 C10 -0.8(3) . . . . ?
C5 C6 C11 C2 0.6(3) . . . . ?
C7 C6 C11 C2 179.1(2) . . . . ?
Cu1 O2 C12 N1 0.8(2) . . . . ?
Cu1 O2 C12 C10 -179.24(15) . . . . ?
C1 N1 C12 O2 -172.78(19) . . . . ?
N2 N1 C12 O2 3.9(3) . . . . ?
C1 N1 C12 C10 7.2(3) . . . . ?
N2 N1 C12 C10 -176.07(17) . . . . ?
C9 C10 C12 O2 -3.3(3) . . . . ?
C11 C10 C12 O2 178.65(19) . . . . ?
C9 C10 C12 N1 176.68(19) . . . . ?
C11 C10 C12 N1 -1.4(3) . . . . ?

_refine_diff_density_max         0.430
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_ns212
_database_code_depnum_ccdc_archive 'CCDC 1462846'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H24 Cu N6 O10'
_chemical_formula_sum            'C36 H24 Cu N6 O10'
_chemical_formula_weight         764.15

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   Pbcn
_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+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   27.0677(13)
_cell_length_b                   7.5081(3)
_cell_length_c                   16.0875(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3269.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9997
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      26.00
_exptl_crystal_description       block
_exptl_crystal_colour            'pale blue'
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1564
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.684
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'SADABS; (sheldrick, 2003)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'INCOATEC Imus micro-focus source'
_diffrn_radiation_monochromator  mirrors
_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            59973
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3210
_reflns_number_gt                2411
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Siemens)'
_computing_publication_material  SHELXL-97

_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)+(0.0540P)²+1.5793P] 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         3210
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0984
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_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 0.5000 0.35790(5) 0.2500 0.03169(13) Uani 1 2 d S . .
N1 N 0.46395(7) 0.1737(2) 0.31409(11) 0.0324(4) Uani 1 1 d . . .
N2 N 0.34673(7) -0.2129(2) 0.47756(11) 0.0340(4) Uani 1 1 d . . .
N3 N 0.52770(10) 0.5773(3) 0.36562(15) 0.0606(6) Uani 1 1 d . . .
O1 O 0.38110(7) -0.1085(3) 0.59644(11) 0.0638(6) Uani 1 1 d . . .
O2 O 0.31373(7) -0.2910(3) 0.35399(11) 0.0589(5) Uani 1 1 d . . .
O3 O 0.48542(7) 0.5447(2) 0.33452(11) 0.0491(4) Uani 1 1 d . . .
O4 O 0.53199(11) 0.6921(4) 0.41805(17) 0.1153(11) Uani 1 1 d . . .
O5 O 0.56233(8) 0.4852(3) 0.34030(15) 0.0846(8) Uani 1 1 d . . .
C1 C 0.46664(8) 0.1618(3) 0.39697(13) 0.0364(5) Uani 1 1 d . . .
H1 H 0.4842 0.2511 0.4267 0.044 Uiso 1 1 calc R . .
C2 C 0.44501(8) 0.0254(3) 0.44062(14) 0.0388(5) Uani 1 1 d . . .
H2 H 0.4477 0.0215 0.4995 0.047 Uiso 1 1 calc R . .
C3 C 0.41935(8) -0.1059(3) 0.39898(14) 0.0334(5) Uani 1 1 d . . .
C4 C 0.41598(9) -0.0920(3) 0.31370(15) 0.0431(6) Uani 1 1 d . . .
H4 H 0.3983 -0.1790 0.2828 0.052 Uiso 1 1 calc R . .
C5 C 0.43834(9) 0.0483(3) 0.27347(14) 0.0420(6) Uani 1 1 d . . .
H5 H 0.4355 0.0565 0.2147 0.050 Uiso 1 1 calc R . .
C6 C 0.39617(8) -0.2593(3) 0.44556(15) 0.0426(6) Uani 1 1 d . . .
H6A H 0.3934 -0.3633 0.4080 0.051 Uiso 1 1 calc R . .
H6B H 0.4178 -0.2933 0.4926 0.051 Uiso 1 1 calc R . .
C7 C 0.34350(9) -0.1391(3) 0.55756(14) 0.0399(6) Uani 1 1 d . . .
C8 C 0.29349(10) -0.1039(3) 0.58936(14) 0.0405(6) Uani 1 1 d . . .
C9 C 0.28750(12) -0.0336(3) 0.66845(15) 0.0570(8) Uani 1 1 d . . .
H9 H 0.3156 -0.0041 0.7011 0.068 Uiso 1 1 calc R . .
C10 C 0.23983(15) -0.0064(4) 0.69997(18) 0.0711(10) Uani 1 1 d . . .
H10 H 0.2358 0.0416 0.7542 0.085 Uiso 1 1 calc R . .
C11 C 0.19955(14) -0.0472(4) 0.6545(2) 0.0715(10) Uani 1 1 d . . .
H11 H 0.1677 -0.0290 0.6778 0.086 Uiso 1 1 calc R . .
C12 C 0.20360(10) -0.1162(3) 0.57346(18) 0.0516(7) Uani 1 1 d . . .
C13 C 0.25186(9) -0.1447(3) 0.54092(14) 0.0383(5) Uani 1 1 d . . .
C14 C 0.25713(9) -0.2114(3) 0.45940(14) 0.0366(5) Uani 1 1 d . . .
C15 C 0.21612(9) -0.2488(3) 0.41249(17) 0.0489(7) Uani 1 1 d . . .
H15 H 0.2199 -0.2929 0.3575 0.059 Uiso 1 1 calc R . .
C16 C 0.16872(10) -0.2224(4) 0.4450(2) 0.0630(8) Uani 1 1 d . . .
H16 H 0.1406 -0.2491 0.4119 0.076 Uiso 1 1 calc R . .
C17 C 0.16270(11) -0.1591(4) 0.5230(2) 0.0664(9) Uani 1 1 d . . .
H17 H 0.1303 -0.1433 0.5443 0.080 Uiso 1 1 calc R . .
C18 C 0.30663(8) -0.2416(3) 0.42478(14) 0.0372(5) 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 1.9819(17) . ?
Cu1 N1 1.9819(17) 4_655 ?
Cu1 O3 1.9930(16) . ?
Cu1 O3 1.9930(16) 4_655 ?
Cu1 O5 2.423(2) . ?
Cu1 O5 2.423(2) 4_655 ?
N1 C1 1.338(3) . ?
N1 C5 1.339(3) . ?
N2 C18 1.395(3) . ?
N2 C7 1.404(3) . ?
N2 C6 1.476(3) . ?
N3 O4 1.212(3) . ?
N3 O5 1.234(3) . ?
N3 O3 1.272(3) . ?
O1 C7 1.217(3) . ?
O2 C18 1.213(3) . ?
C1 C2 1.373(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.380(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(3) . ?
C3 C6 1.511(3) . ?
C4 C5 1.377(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.471(4) . ?
C8 C9 1.387(3) . ?
C8 C13 1.404(3) . ?
C9 C10 1.401(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.348(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.408(4) . ?
C11 H11 0.9500 . ?
C12 C17 1.410(4) . ?
C12 C13 1.424(3) . ?
C13 C14 1.411(3) . ?
C14 C15 1.371(3) . ?
C14 C18 1.469(3) . ?
C15 C16 1.399(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.353(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

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 N1 91.50(10) . 4_655 ?
N1 Cu1 O3 92.22(7) . . ?
N1 Cu1 O3 160.65(7) 4_655 . ?
N1 Cu1 O3 160.65(7) . 4_655 ?
N1 Cu1 O3 92.22(7) 4_655 4_655 ?
O3 Cu1 O3 90.53(10) . 4_655 ?
N1 Cu1 O5 107.83(8) . . ?
N1 Cu1 O5 104.15(7) 4_655 . ?
O3 Cu1 O5 56.71(7) . . ?
O3 Cu1 O5 89.63(8) 4_655 . ?
N1 Cu1 O5 104.15(7) . 4_655 ?
N1 Cu1 O5 107.83(8) 4_655 4_655 ?
O3 Cu1 O5 89.63(8) . 4_655 ?
O3 Cu1 O5 56.71(7) 4_655 4_655 ?
O5 Cu1 O5 133.53(11) . 4_655 ?
C1 N1 C5 117.87(19) . . ?
C1 N1 Cu1 122.55(15) . . ?
C5 N1 Cu1 119.43(15) . . ?
C18 N2 C7 124.8(2) . . ?
C18 N2 C6 117.19(19) . . ?
C7 N2 C6 118.01(19) . . ?
O4 N3 O5 123.7(3) . . ?
O4 N3 O3 119.8(3) . . ?
O5 N3 O3 116.5(2) . . ?
N3 O3 Cu1 103.02(14) . . ?
N3 O5 Cu1 83.67(14) . . ?
N1 C1 C2 122.4(2) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 117.5(2) . . ?
C4 C3 C6 121.6(2) . . ?
C2 C3 C6 120.9(2) . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
N1 C5 C4 122.4(2) . . ?
N1 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
N2 C6 C3 111.68(18) . . ?
N2 C6 H6A 109.3 . . ?
C3 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C3 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
O1 C7 N2 119.6(2) . . ?
O1 C7 C8 123.9(2) . . ?
N2 C7 C8 116.6(2) . . ?
C9 C8 C13 119.9(2) . . ?
C9 C8 C7 119.7(3) . . ?
C13 C8 C7 120.4(2) . . ?
C8 C9 C10 119.7(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 121.0(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 121.5(3) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C17 123.8(3) . . ?
C11 C12 C13 117.9(3) . . ?
C17 C12 C13 118.3(3) . . ?
C8 C13 C14 120.8(2) . . ?
C8 C13 C12 120.0(2) . . ?
C14 C13 C12 119.2(2) . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 C18 119.9(2) . . ?
C13 C14 C18 120.0(2) . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C12 121.3(3) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
O2 C18 N2 119.7(2) . . ?
O2 C18 C14 123.2(2) . . ?
N2 C18 C14 117.1(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.049
