# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_LH2
_database_code_depnum_ccdc_archive 'CCDC 1508663'
_audit_update_record             
;
2016-10-06 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H10 N4'
_chemical_formula_weight         162.20

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'

_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                   5.57982(8)
_cell_length_b                   4.79015(7)
_cell_length_c                   15.1644(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.0417(8)
_cell_angle_gamma                90
_cell_volume                     404.310(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3879
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      26.76

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             172
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6969
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9615
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.693
_diffrn_reflns_theta_max         28.415
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1021
_reflns_number_gt                844
_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-2014 (Sheldrick 2014)'
_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)+(0.0480P)²+0.1015P]
 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         1021
_refine_ls_number_parameters     58
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1027
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
N1 N 0.94868(17) 0.2167(2) 0.33138(6) 0.0330(3) Uani 1 1 d . . . . .
N2 N 0.78558(18) 0.0338(2) 0.29446(6) 0.0343(3) Uani 1 1 d . . . . .
H2N H 0.828(2) -0.078(3) 0.2519(9) 0.041 Uiso 1 1 d . U . . .
C1 C 0.5793(2) 0.0393(3) 0.33376(8) 0.0388(3) Uani 1 1 d . . . . .
H1 H 0.4440 -0.0692 0.3193 0.047 Uiso 1 1 calc R U . . .
C2 C 0.6049(2) 0.2352(3) 0.39948(8) 0.0399(3) Uani 1 1 d . . . . .
H2 H 0.4913 0.2871 0.4384 0.048 Uiso 1 1 calc R U . . .
C3 C 0.8377(2) 0.3408(2) 0.39582(7) 0.0306(3) Uani 1 1 d . . . . .
C4 C 0.9656(2) 0.5551(2) 0.45354(7) 0.0355(3) Uani 1 1 d . . . . .
H4A H 0.8629 0.7173 0.4577 0.043 Uiso 1 1 calc R U . . .
H4B H 1.1099 0.6138 0.4265 0.043 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
N1 C3 1.3330(15) . ?
N1 N2 1.3556(14) . ?
N2 C1 1.3331(16) . ?
C1 C2 1.3689(18) . ?
C2 C3 1.3992(17) . ?
C3 C4 1.4969(15) . ?
C4 C4 1.528(2) 3_766 ?

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
C3 N1 N2 104.96(9) . . ?
C1 N2 N1 112.22(10) . . ?
N2 C1 C2 106.87(11) . . ?
C1 C2 C3 105.57(11) . . ?
N1 C3 C2 110.38(10) . . ?
N1 C3 C4 120.50(10) . . ?
C2 C3 C4 129.09(11) . . ?
C3 C4 C4 112.38(12) . 3_766 ?

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.035

_shelxl_version_number           2013-2


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: water, ethanol'
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1508664'
_audit_update_record             
;
2016-10-06 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H69 Cu4 N17 O'
_chemical_formula_weight         1154.36

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'

_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                   19.4050(6)
_cell_length_b                   13.4239(4)
_cell_length_c                   19.5853(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.268(2)
_cell_angle_gamma                90
_cell_volume                     5087.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9906
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      24.00

_exptl_crystal_description       plate
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_F_000             2400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.705
_shelx_estimated_absorpt_T_min   0.438
_shelx_estimated_absorpt_T_max   0.920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5449
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            73685
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.052
_diffrn_reflns_theta_max         24.614
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.927
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.927
_reflns_number_total             8533
_reflns_number_gt                6781
_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-2014/6 (Sheldrick, 2014)'
_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)+(0.0181P)²+59.0798P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8533
_refine_ls_number_parameters     612
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0787
_refine_ls_wR_factor_ref         0.1693
_refine_ls_wR_factor_gt          0.1586
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.097
_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 1.09386(4) 0.41573(7) 0.46558(4) 0.0286(2) Uani 1 1 d . . . . .
Cu2 Cu 0.99580(4) 0.39370(6) 0.58714(4) 0.0278(2) Uani 1 1 d . . . . .
Cu3 Cu 0.39009(5) 0.03535(8) 0.52885(5) 0.0385(3) Uani 1 1 d . . . . .
Cu4 Cu 0.48524(5) 0.10441(9) 0.41388(5) 0.0447(3) Uani 1 1 d . . . . .
O1 O 1.0000 0.5000 0.5000 0.0343(17) Uani 1 2 d S . P . .
O2 O 0.5000 0.0000 0.5000 0.048(2) Uani 1 2 d S . P . .
N1 N 1.1395(3) 0.3999(5) 0.5604(3) 0.0366(15) Uani 1 1 d . . . . .
N2 N 1.0959(3) 0.3921(4) 0.6100(3) 0.0315(14) Uani 1 1 d . . . . .
N3 N 0.9845(3) 0.5020(5) 0.6554(3) 0.0366(15) Uani 1 1 d . . . . .
N4 N 0.9408(3) 0.5771(5) 0.6348(3) 0.0295(14) Uani 1 1 d . . . . .
N5 N 1.0470(3) 0.2837(5) 0.4771(3) 0.0338(15) Uani 1 1 d . . . . .
N6 N 1.0032(3) 0.2725(5) 0.5271(3) 0.0319(14) Uani 1 1 d . . . . .
N7 N 0.8957(3) 0.3833(4) 0.5772(3) 0.0302(14) Uani 1 1 d . . . . .
N8 N 0.8549(3) 0.4557(5) 0.5488(3) 0.0322(14) Uani 1 1 d . . . . .
N17 N 0.2410(4) 0.5534(6) 0.2353(3) 0.0457(19) Uani 1 1 d . . . . .
C1 C 1.2043(4) 0.4018(7) 0.5893(5) 0.049(2) Uani 1 1 d . . . . .
H1 H 1.2441 0.4069 0.5658 0.059 Uiso 1 1 calc R U . . .
C2 C 1.2026(4) 0.3950(6) 0.6597(4) 0.048(2) Uani 1 1 d . . . . .
H2 H 1.2400 0.3943 0.6923 0.057 Uiso 1 1 calc R U . . .
C3 C 1.1335(4) 0.3895(6) 0.6707(4) 0.040(2) Uani 1 1 d . . . . .
C4 C 1.1005(6) 0.3823(10) 0.7346(5) 0.081(4) Uani 1 1 d . . . . .
H4A H 1.0699 0.3252 0.7301 0.098 Uiso 1 1 calc R U . . .
H4B H 1.1367 0.3651 0.7695 0.098 Uiso 1 1 calc R U . . .
C5 C 1.0627(9) 0.4589(12) 0.7616(5) 0.131(7) Uani 1 1 d . . . . .
H5A H 1.0964 0.5070 0.7802 0.157 Uiso 1 1 calc R U . . .
H5B H 1.0415 0.4305 0.8005 0.157 Uiso 1 1 calc R U . . .
C6 C 1.0063(5) 0.5190(7) 0.7221(4) 0.054(3) Uani 1 1 d . . . . .
C7 C 0.9749(4) 0.6028(7) 0.7445(4) 0.046(2) Uani 1 1 d . . . . .
H7 H 0.9795 0.6306 0.7881 0.056 Uiso 1 1 calc R U . . .
C8 C 0.9353(4) 0.6368(6) 0.6887(4) 0.0365(19) Uani 1 1 d . . . . .
H8 H 0.9082 0.6940 0.6883 0.044 Uiso 1 1 calc R U . . .
C9 C 1.0452(4) 0.1993(6) 0.4398(4) 0.042(2) Uani 1 1 d . . . . .
H9 H 1.0713 0.1873 0.4027 0.051 Uiso 1 1 calc R U . . .
C10 C 0.9996(5) 0.1343(6) 0.4646(4) 0.043(2) Uani 1 1 d . . . . .
H10 H 0.9882 0.0712 0.4477 0.052 Uiso 1 1 calc R U . . .
C11 C 0.9737(4) 0.1812(5) 0.5199(4) 0.0363(19) Uani 1 1 d . . . . .
C12 C 0.9194(5) 0.1414(6) 0.5633(4) 0.051(2) Uani 1 1 d . . . . .
H12A H 0.9385 0.0833 0.5872 0.061 Uiso 1 1 calc R U . . .
H12B H 0.8811 0.1186 0.5327 0.061 Uiso 1 1 calc R U . . .
C13 C 0.8903(5) 0.2089(7) 0.6159(4) 0.050(2) Uani 1 1 d . . . . .
H13A H 0.8570 0.1716 0.6401 0.060 Uiso 1 1 calc R U . . .
H13B H 0.9275 0.2286 0.6490 0.060 Uiso 1 1 calc R U . . .
C14 C 0.8557(4) 0.3017(6) 0.5857(4) 0.0378(19) Uani 1 1 d . . . . .
C15 C 0.7888(5) 0.3229(7) 0.5626(4) 0.046(2) Uani 1 1 d . . . . .
H15 H 0.7507 0.2809 0.5625 0.055 Uiso 1 1 calc R U . . .
C16 C 0.7904(4) 0.4206(7) 0.5392(4) 0.043(2) Uani 1 1 d . . . . .
H16 H 0.7526 0.4560 0.5199 0.052 Uiso 1 1 calc R U . . .
C17A C 0.3693(13) 0.2545(16) 0.5573(13) 0.073(8) Uiso 0.5 1 d D . P A 1
H17A H 0.3362 0.2488 0.5891 0.087 Uiso 0.5 1 calc R U P A 1
C18A C 0.4018(14) 0.340(2) 0.5394(16) 0.099(11) Uiso 0.5 1 d D . P A 1
H18A H 0.3935 0.4036 0.5558 0.119 Uiso 0.5 1 calc R U P A 1
C19A C 0.4492(13) 0.3156(16) 0.4927(13) 0.071(7) Uiso 0.5 1 d D . P A 1
C20A C 0.5026(16) 0.386(2) 0.4722(19) 0.142(15) Uiso 0.5 1 d D . P A 1
H20A H 0.4804 0.4484 0.4593 0.171 Uiso 0.5 1 calc R U P A 1
H20B H 0.5345 0.3987 0.5118 0.171 Uiso 0.5 1 calc R U P A 1
C22A C 0.5939(9) 0.2659(16) 0.4258(11) 0.042(5) Uiso 0.5 1 d D . P A 1
C21A C 0.5432(15) 0.352(2) 0.4148(14) 0.091(8) Uiso 0.5 1 d D . P A 1
H21A H 0.5691 0.4091 0.4001 0.110 Uiso 0.5 1 calc R U P A 1
H21B H 0.5105 0.3343 0.3770 0.110 Uiso 0.5 1 calc R U P A 1
C23A C 0.6652(9) 0.2723(18) 0.4348(11) 0.041(7) Uiso 0.5 1 d D . P A 1
H23A H 0.6927 0.3284 0.4308 0.049 Uiso 0.5 1 calc R U P A 1
C24A C 0.6852(9) 0.1795(16) 0.4507(9) 0.021(4) Uiso 0.5 1 d . . P A 1
H24A H 0.7305 0.1592 0.4614 0.025 Uiso 0.5 1 calc R U P A 1
N9A N 0.3945(9) 0.1798(13) 0.5202(10) 0.035(5) Uiso 0.5 1 d D . P A 1
N10A N 0.4429(12) 0.2168(16) 0.4814(12) 0.060(7) Uiso 0.5 1 d D . P A 1
N11A N 0.5723(8) 0.1722(12) 0.4349(8) 0.034(4) Uiso 0.5 1 d . . P A 1
N12A N 0.6282(9) 0.1188(13) 0.4486(8) 0.026(5) Uiso 0.5 1 d . . P A 1
C25A C 0.2897(10) 0.0001(16) 0.3984(10) 0.039(5) Uiso 0.5 1 d . . P A 1
H25A H 0.2528 -0.0316 0.4171 0.046 Uiso 0.5 1 calc R U P A 1
C26A C 0.2944(10) 0.0176(16) 0.3309(10) 0.044(5) Uiso 0.5 1 d . . P A 1
H26A H 0.2630 0.0008 0.2945 0.053 Uiso 0.5 1 calc R U P A 1
C27A C 0.3567(8) 0.0662(14) 0.3287(9) 0.036(4) Uiso 0.5 1 d . . P A 1
C28A C 0.3996(10) 0.0978(15) 0.2659(10) 0.054(5) Uiso 0.5 1 d D . P A 1
H28A H 0.4301 0.1524 0.2804 0.065 Uiso 0.5 1 calc R U P A 1
H28B H 0.3676 0.1224 0.2294 0.065 Uiso 0.5 1 calc R U P A 1
C29A C 0.4445(10) 0.0117(16) 0.2364(10) 0.054(5) Uiso 0.5 1 d D . P A 1
H29A H 0.4190 -0.0505 0.2338 0.065 Uiso 0.5 1 calc R U P A 1
H29B H 0.4580 0.0286 0.1912 0.065 Uiso 0.5 1 calc R U P A 1
C30A C 0.5014(8) 0.0042(14) 0.2821(8) 0.033(4) Uiso 0.5 1 d D . P A 1
C31A C 0.5449(10) -0.0719(14) 0.2603(10) 0.049(5) Uiso 0.5 1 d D . P A 1
H31A H 0.5462 -0.0971 0.2161 0.059 Uiso 0.5 1 calc R U P A 1
C32A C 0.5854(11) -0.1011(18) 0.3181(11) 0.049(6) Uiso 0.5 1 d . . P A 1
H32A H 0.6173 -0.1528 0.3215 0.059 Uiso 0.5 1 calc R U P A 1
N13A N 0.3464(8) 0.0356(13) 0.4347(8) 0.030(4) Uiso 0.5 1 d . . P A 1
N14A N 0.3873(8) 0.0762(13) 0.3924(9) 0.044(5) Uiso 0.5 1 d . . P A 1
N15A N 0.5180(8) 0.0275(13) 0.3488(8) 0.037(5) Uiso 0.5 1 d . . P A 1
N16A N 0.5682(10) -0.0378(14) 0.3694(9) 0.039(5) Uiso 0.5 1 d . . P A 1
C17B C 0.3756(10) 0.2645(13) 0.5327(11) 0.043(5) Uiso 0.5 1 d D . P A 2
H17B H 0.3403 0.2641 0.5623 0.052 Uiso 0.5 1 calc R U P A 2
C18B C 0.4084(10) 0.3459(15) 0.5106(11) 0.043(4) Uiso 0.5 1 d . . P A 2
H18B H 0.4013 0.4118 0.5229 0.052 Uiso 0.5 1 calc R U P A 2
C19B C 0.4565(10) 0.3094(15) 0.4642(11) 0.049(5) Uiso 0.5 1 d . . P A 2
C20B C 0.5107(10) 0.3701(14) 0.4349(10) 0.044(4) Uiso 0.5 1 d . . P A 2
H20C H 0.5423 0.3933 0.4723 0.052 Uiso 0.5 1 calc R U P A 2
H20D H 0.4889 0.4284 0.4136 0.052 Uiso 0.5 1 calc R U P A 2
C21B C 0.5527(8) 0.3194(13) 0.3828(9) 0.038(4) Uiso 0.5 1 d . . P A 2
H21C H 0.5761 0.3706 0.3583 0.046 Uiso 0.5 1 calc R U P A 2
H21D H 0.5209 0.2859 0.3498 0.046 Uiso 0.5 1 calc R U P A 2
C22B C 0.6062(10) 0.2443(16) 0.4100(11) 0.042(5) Uiso 0.5 1 d . . P A 2
C23B C 0.6756(10) 0.247(2) 0.4321(11) 0.034(6) Uiso 0.5 1 d . . P A 2
H23B H 0.7056 0.3012 0.4309 0.041 Uiso 0.5 1 calc R U P A 2
C24B C 0.6911(10) 0.1495(15) 0.4568(10) 0.032(6) Uiso 0.5 1 d . . P A 2
H24B H 0.7345 0.1285 0.4744 0.038 Uiso 0.5 1 calc R U P A 2
N9B N 0.4036(12) 0.1841(15) 0.5040(11) 0.049(7) Uiso 0.5 1 d D . P A 2
N10B N 0.4511(9) 0.2085(13) 0.4627(10) 0.038(5) Uiso 0.5 1 d . . P A 2
N11B N 0.5833(8) 0.1488(12) 0.4225(8) 0.027(4) Uiso 0.5 1 d . . P A 2
N12B N 0.6362(8) 0.0936(13) 0.4516(8) 0.027(5) Uiso 0.5 1 d . . P A 2
C25B C 0.2962(9) -0.0324(14) 0.3993(9) 0.026(4) Uiso 0.5 1 d . . P A 2
H25B H 0.2602 -0.0607 0.4214 0.031 Uiso 0.5 1 calc R U P A 2
C26B C 0.2988(9) -0.0237(15) 0.3274(9) 0.037(4) Uiso 0.5 1 d . . P A 2
H26B H 0.2652 -0.0433 0.2937 0.044 Uiso 0.5 1 calc R U P A 2
C27B C 0.3612(8) 0.0197(14) 0.3180(8) 0.031(4) Uiso 0.5 1 d . . P A 2
C28B C 0.3850(10) 0.037(2) 0.2537(12) 0.072(6) Uiso 0.5 1 d D . P A 2
H28C H 0.3762 -0.0235 0.2276 0.086 Uiso 0.5 1 calc R U P A 2
H28D H 0.3548 0.0876 0.2323 0.086 Uiso 0.5 1 calc R U P A 2
C29B C 0.4546(9) 0.0670(19) 0.2421(12) 0.065(6) Uiso 0.5 1 d D . P A 2
H29C H 0.4667 0.1293 0.2651 0.078 Uiso 0.5 1 calc R U P A 2
H29D H 0.4606 0.0740 0.1936 0.078 Uiso 0.5 1 calc R U P A 2
C30B C 0.5079(10) -0.0408(16) 0.2809(9) 0.041(4) Uiso 0.5 1 d . . P A 2
C31B C 0.5450(10) -0.1189(17) 0.2724(10) 0.053(5) Uiso 0.5 1 d D . P A 2
H31B H 0.5429 -0.1588 0.2335 0.064 Uiso 0.5 1 calc R U P A 2
C32B C 0.5883(11) -0.1334(19) 0.3304(10) 0.053(6) Uiso 0.5 1 d D . P A 2
H32B H 0.6203 -0.1847 0.3365 0.063 Uiso 0.5 1 calc R U P A 2
N13B N 0.3540(8) 0.0069(12) 0.4303(8) 0.027(4) Uiso 0.5 1 d . . P A 2
N14B N 0.3935(6) 0.0455(11) 0.3800(7) 0.021(3) Uiso 0.5 1 d . . P A 2
N15B N 0.5264(8) -0.0051(12) 0.3460(7) 0.025(4) Uiso 0.5 1 d . . P A 2
N16B N 0.5780(7) -0.0651(12) 0.3755(7) 0.022(4) Uiso 0.5 1 d . . P A 2
C33 C 0.2356(5) 0.4914(7) 0.1699(4) 0.049(2) Uani 1 1 d . . . . .
H33A H 0.2479 0.5333 0.1323 0.059 Uiso 1 1 calc R U . . .
H33B H 0.2694 0.4382 0.1748 0.059 Uiso 1 1 calc R U . . .
C34 C 0.1655(5) 0.4457(9) 0.1509(4) 0.066(3) Uani 1 1 d . . . . .
H34A H 0.1335 0.4976 0.1346 0.080 Uiso 1 1 calc R U . . .
H34B H 0.1479 0.4158 0.1912 0.080 Uiso 1 1 calc R U . . .
C35 C 0.1694(6) 0.3662(8) 0.0951(5) 0.065(3) Uani 1 1 d . . . . .
H35A H 0.1990 0.3125 0.1129 0.078 Uiso 1 1 calc R U . . .
H35B H 0.1235 0.3387 0.0847 0.078 Uiso 1 1 calc R U . . .
C36 C 0.1958(5) 0.4030(8) 0.0310(5) 0.067(3) Uani 1 1 d . . . . .
H36A H 0.1677 0.4576 0.0137 0.100 Uiso 1 1 calc R U . . .
H36B H 0.1941 0.3502 -0.0022 0.100 Uiso 1 1 calc R U . . .
H36C H 0.2427 0.4249 0.0399 0.100 Uiso 1 1 calc R U . . .
C37 C 0.1849(4) 0.6310(8) 0.2341(4) 0.050(2) Uani 1 1 d . . . . .
H37A H 0.1896 0.6676 0.2769 0.060 Uiso 1 1 calc R U . . .
H37B H 0.1406 0.5973 0.2320 0.060 Uiso 1 1 calc R U . . .
C38 C 0.1844(4) 0.7044(8) 0.1759(4) 0.051(2) Uani 1 1 d . . . . .
H38A H 0.2268 0.7428 0.1801 0.062 Uiso 1 1 calc R U . . .
H38B H 0.1831 0.6681 0.1330 0.062 Uiso 1 1 calc R U . . .
C39 C 0.1242(5) 0.7743(9) 0.1741(5) 0.066(3) Uani 1 1 d . . . . .
H39A H 0.1264 0.8126 0.2162 0.079 Uiso 1 1 calc R U . . .
H39B H 0.0817 0.7359 0.1717 0.079 Uiso 1 1 calc R U . . .
C40 C 0.1227(5) 0.8440(8) 0.1147(5) 0.059(3) Uani 1 1 d . . . . .
H40A H 0.1653 0.8805 0.1159 0.088 Uiso 1 1 calc R U . . .
H40B H 0.0849 0.8898 0.1171 0.088 Uiso 1 1 calc R U . . .
H40C H 0.1168 0.8068 0.0728 0.088 Uiso 1 1 calc R U . . .
C41 C 0.3126(4) 0.5996(7) 0.2407(4) 0.0394(19) Uani 1 1 d . . . . .
H41A H 0.3464 0.5464 0.2407 0.047 Uiso 1 1 calc R U . . .
H41B H 0.3175 0.6396 0.2001 0.047 Uiso 1 1 calc R U . . .
C42 C 0.3297(5) 0.6641(8) 0.3028(4) 0.054(3) Uani 1 1 d . . . . .
H42A H 0.2968 0.7187 0.3024 0.065 Uiso 1 1 calc R U . . .
H42B H 0.3239 0.6249 0.3436 0.065 Uiso 1 1 calc R U . . .
C43 C 0.3999(5) 0.7057(7) 0.3073(5) 0.057(3) Uani 1 1 d . . . . .
H43A H 0.4043 0.7488 0.2681 0.069 Uiso 1 1 calc R U . . .
H43B H 0.4324 0.6513 0.3040 0.069 Uiso 1 1 calc R U . . .
C44 C 0.4201(5) 0.7638(8) 0.3712(5) 0.066(3) Uani 1 1 d . . . . .
H44A H 0.3910 0.8214 0.3731 0.099 Uiso 1 1 calc R U . . .
H44B H 0.4674 0.7846 0.3707 0.099 Uiso 1 1 calc R U . . .
H44C H 0.4148 0.7227 0.4106 0.099 Uiso 1 1 calc R U . . .
C45 C 0.2312(5) 0.4859(7) 0.2972(4) 0.063(3) Uani 1 1 d D . . . .
H45A H 0.2509 0.5196 0.3380 0.075 Uiso 1 1 calc R U . B 3
H45B H 0.1821 0.4790 0.3019 0.075 Uiso 1 1 calc R U . B 3
C46A C 0.2605(10) 0.3888(12) 0.2957(8) 0.047(5) Uiso 0.5 1 d D . P C 3
H46A H 0.3083 0.3917 0.2843 0.057 Uiso 0.5 1 calc R U P C 3
H46B H 0.2346 0.3468 0.2626 0.057 Uiso 0.5 1 calc R U P C 3
C47A C 0.2553(8) 0.3505(11) 0.3677(7) 0.037(4) Uiso 0.5 1 d D . P C 3
H47A H 0.2076 0.3488 0.3794 0.044 Uiso 0.5 1 calc R U P C 3
H47B H 0.2820 0.3916 0.4007 0.044 Uiso 0.5 1 calc R U P C 3
C48A C 0.2860(9) 0.2439(11) 0.3652(9) 0.046(4) Uiso 0.5 1 d D . P C 3
H48A H 0.2564 0.2031 0.3353 0.069 Uiso 0.5 1 calc R U P C 3
H48B H 0.2894 0.2158 0.4103 0.069 Uiso 0.5 1 calc R U P C 3
H48C H 0.3311 0.2470 0.3482 0.069 Uiso 0.5 1 calc R U P C 3
C46B C 0.2915(11) 0.4018(16) 0.3081(10) 0.069(6) Uiso 0.5 1 d D . P C 4
H46C H 0.2827 0.3535 0.2717 0.082 Uiso 0.5 1 calc R U P C 4
H46D H 0.3346 0.4347 0.2995 0.082 Uiso 0.5 1 calc R U P C 4
C47B C 0.3059(10) 0.3415(16) 0.3747(10) 0.068(6) Uiso 0.5 1 d D . P C 4
H47C H 0.3418 0.2929 0.3680 0.081 Uiso 0.5 1 calc R U P C 4
H47D H 0.3229 0.3862 0.4111 0.081 Uiso 0.5 1 calc R U P C 4
C48B C 0.2420(11) 0.2874(19) 0.3966(12) 0.081(7) Uiso 0.5 1 d D . P C 4
H48D H 0.2032 0.3320 0.3933 0.122 Uiso 0.5 1 calc R U P C 4
H48E H 0.2502 0.2652 0.4431 0.122 Uiso 0.5 1 calc R U P C 4
H48F H 0.2323 0.2310 0.3673 0.122 Uiso 0.5 1 calc R U P C 4


_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 2.009(6) . ?
Cu1 N5 2.012(7) . ?
Cu1 N8 2.021(6) 3_766 ?
Cu1 N4 2.032(6) 3_766 ?
Cu1 O1 2.2878(9) . ?
Cu2 N7 1.943(6) . ?
Cu2 N2 1.961(6) . ?
Cu2 N3 1.998(6) . ?
Cu2 N6 2.019(6) . ?
Cu2 O1 2.2307(8) . ?
Cu3 N12B 1.853(17) 3_656 ?
Cu3 N9A 1.948(17) . ?
Cu3 N16B 1.971(14) 3_656 ?
Cu3 N13A 1.972(15) . ?
Cu3 N13B 2.039(15) . ?
Cu3 N9B 2.08(2) . ?
Cu3 N16A 2.094(19) 3_656 ?
Cu3 N12A 2.150(17) 3_656 ?
Cu3 O2 2.2963(9) . ?
Cu4 N15A 1.794(17) . ?
Cu4 N10B 1.844(19) . ?
Cu4 N11A 1.936(16) . ?
Cu4 N14A 1.953(16) . ?
Cu4 N11B 1.989(15) . ?
Cu4 N14B 2.015(13) . ?
Cu4 N15B 2.173(16) . ?
Cu4 O2 2.1954(10) . ?
Cu4 N10A 2.21(2) . ?
O1 Cu2 2.2307(8) 3_766 ?
O1 Cu1 2.2879(9) 3_766 ?
O2 Cu4 2.1954(10) 3_656 ?
O2 Cu3 2.2963(9) 3_656 ?
N1 N2 1.339(9) . ?
N1 C1 1.339(10) . ?
N2 C3 1.349(9) . ?
N3 C6 1.362(10) . ?
N3 N4 1.359(9) . ?
N4 C8 1.336(9) . ?
N4 Cu1 2.032(6) 3_766 ?
N5 C9 1.347(10) . ?
N5 N6 1.352(8) . ?
N6 C11 1.357(10) . ?
N7 N8 1.347(8) . ?
N7 C14 1.360(9) . ?
N8 C16 1.337(10) . ?
N8 Cu1 2.021(6) 3_766 ?
N17 C37 1.506(12) . ?
N17 C33 1.523(10) . ?
N17 C41 1.518(10) . ?
N17 C45 1.537(10) . ?
C1 C2 1.384(12) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.450(13) . ?
C4 C5 1.390(16) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.524(14) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.368(13) . ?
C7 C8 1.366(11) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.358(12) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.499(12) . ?
C12 C13 1.512(12) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.514(12) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.372(12) . ?
C15 C16 1.391(12) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17A N9A 1.351(17) . ?
C17A C18A 1.368(19) . ?
C17A H17A 0.9300 . ?
C18A C19A 1.385(18) . ?
C18A H18A 0.9300 . ?
C19A N10A 1.349(18) . ?
C19A C20A 1.478(19) . ?
C20A C21A 1.490(19) . ?
C20A H20A 0.9700 . ?
C20A H20B 0.9700 . ?
C22A N11A 1.34(3) . ?
C22A C23A 1.384(17) . ?
C22A C21A 1.52(3) . ?
C21A H21A 0.9700 . ?
C21A H21B 0.9700 . ?
C23A C24A 1.33(3) . ?
C23A H23A 0.9300 . ?
C24A N12A 1.37(2) . ?
C24A H24A 0.9300 . ?
N9A N10A 1.35(3) . ?
N11A N12A 1.31(2) . ?
N12A Cu3 2.150(17) 3_656 ?
C25A N13A 1.35(2) . ?
C25A C26A 1.35(3) . ?
C25A H25A 0.9300 . ?
C26A C27A 1.38(3) . ?
C26A H26A 0.9300 . ?
C27A N14A 1.35(2) . ?
C27A C28A 1.59(2) . ?
C28A C29A 1.582(16) . ?
C28A H28A 0.9700 . ?
C28A H28B 0.9700 . ?
C29A C30A 1.37(2) . ?
C29A H29A 0.9700 . ?
C29A H29B 0.9700 . ?
C30A N15A 1.36(2) . ?
C30A C31A 1.413(17) . ?
C31A C32A 1.39(3) . ?
C31A H31A 0.9300 . ?
C32A N16A 1.38(3) . ?
C32A H32A 0.9300 . ?
N13A N14A 1.31(2) . ?
N15A N16A 1.35(3) . ?
N16A Cu3 2.094(19) 3_656 ?
C17B N9B 1.350(16) . ?
C17B C18B 1.35(3) . ?
C17B H17B 0.9300 . ?
C18B C19B 1.44(3) . ?
C18B H18B 0.9300 . ?
C19B N10B 1.36(3) . ?
C19B C20B 1.48(3) . ?
C20B C21B 1.51(3) . ?
C20B H20C 0.9700 . ?
C20B H20D 0.9700 . ?
C21B C22B 1.52(3) . ?
C21B H21C 0.9700 . ?
C21B H21D 0.9700 . ?
C22B C23B 1.39(3) . ?
C22B N11B 1.38(3) . ?
C23B C24B 1.42(3) . ?
C23B H23B 0.9300 . ?
C24B N12B 1.30(2) . ?
C24B H24B 0.9300 . ?
N9B N10B 1.31(3) . ?
N11B N12B 1.36(2) . ?
N12B Cu3 1.853(17) 3_656 ?
C25B N13B 1.34(2) . ?
C25B C26B 1.42(2) . ?
C25B H25B 0.9300 . ?
C26B C27B 1.37(2) . ?
C26B H26B 0.9300 . ?
C27B N14B 1.37(2) . ?
C27B C28B 1.39(3) . ?
C28B C29B 1.443(17) . ?
C28B H28C 0.9700 . ?
C28B H28D 0.9700 . ?
C29B C30B 1.90(3) . ?
C29B H29C 0.9700 . ?
C29B H29D 0.9700 . ?
C30B C31B 1.29(3) . ?
C30B N15B 1.38(2) . ?
C31B C32B 1.376(17) . ?
C31B H31B 0.9300 . ?
C32B N16B 1.30(3) . ?
C32B H32B 0.9300 . ?
N13B N14B 1.39(2) . ?
N15B N16B 1.38(2) . ?
N16B Cu3 1.971(14) 3_656 ?
C33 C34 1.514(12) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.534(13) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.475(13) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 C38 1.506(13) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.496(13) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C40 1.493(14) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 C42 1.510(11) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C43 1.468(12) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 C44 1.502(13) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 C46A 1.423(15) . ?
C45 C46B 1.628(16) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46A C47A 1.511(15) . ?
C46A H46A 0.9700 . ?
C46A H46B 0.9700 . ?
C47A C48A 1.552(15) . ?
C47A H47A 0.9700 . ?
C47A H47B 0.9700 . ?
C48A H48A 0.9600 . ?
C48A H48B 0.9600 . ?
C48A H48C 0.9600 . ?
C46B C47B 1.543(17) . ?
C46B H46C 0.9700 . ?
C46B H46D 0.9700 . ?
C47B C48B 1.527(17) . ?
C47B H47C 0.9700 . ?
C47B H47D 0.9700 . ?
C48B H48D 0.9600 . ?
C48B H48E 0.9600 . ?
C48B H48F 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
N1 Cu1 N5 88.6(3) . . ?
N1 Cu1 N8 91.8(3) . 3_766 ?
N5 Cu1 N8 176.7(3) . 3_766 ?
N1 Cu1 N4 172.3(3) . 3_766 ?
N5 Cu1 N4 91.7(2) . 3_766 ?
N8 Cu1 N4 87.5(2) 3_766 3_766 ?
N1 Cu1 O1 94.94(18) . . ?
N5 Cu1 O1 91.51(18) . . ?
N8 Cu1 O1 91.68(18) 3_766 . ?
N4 Cu1 O1 92.76(17) 3_766 . ?
N7 Cu2 N2 171.2(2) . . ?
N7 Cu2 N3 87.7(3) . . ?
N2 Cu2 N3 90.7(3) . . ?
N7 Cu2 N6 89.9(2) . . ?
N2 Cu2 N6 90.7(2) . . ?
N3 Cu2 N6 172.9(3) . . ?
N7 Cu2 O1 93.60(17) . . ?
N2 Cu2 O1 95.14(18) . . ?
N3 Cu2 O1 93.34(18) . . ?
N6 Cu2 O1 93.53(17) . . ?
N12B Cu3 N16B 93.7(7) 3_656 3_656 ?
N9A Cu3 N13A 86.3(7) . . ?
N12B Cu3 N13B 86.6(7) 3_656 . ?
N16B Cu3 N13B 178.0(6) 3_656 . ?
N12B Cu3 N9B 171.2(8) 3_656 . ?
N16B Cu3 N9B 89.5(7) 3_656 . ?
N13B Cu3 N9B 89.9(7) . . ?
N9A Cu3 N16A 92.9(8) . 3_656 ?
N13A Cu3 N16A 177.1(7) . 3_656 ?
N9A Cu3 N12A 169.7(7) . 3_656 ?
N13A Cu3 N12A 97.3(7) . 3_656 ?
N16A Cu3 N12A 83.0(7) 3_656 3_656 ?
N12B Cu3 O2 97.7(5) 3_656 . ?
N9A Cu3 O2 97.9(5) . . ?
N16B Cu3 O2 92.5(4) 3_656 . ?
N13A Cu3 O2 96.5(5) . . ?
N13B Cu3 O2 89.4(4) . . ?
N9B Cu3 O2 90.3(6) . . ?
N16A Cu3 O2 86.4(5) 3_656 . ?
N12A Cu3 O2 91.3(5) 3_656 . ?
N15A Cu4 N11A 94.1(7) . . ?
N15A Cu4 N14A 97.3(7) . . ?
N11A Cu4 N14A 163.1(7) . . ?
N10B Cu4 N11B 96.2(7) . . ?
N10B Cu4 N14B 97.2(7) . . ?
N11B Cu4 N14B 164.1(6) . . ?
N10B Cu4 N15B 172.9(7) . . ?
N11B Cu4 N15B 82.0(6) . . ?
N14B Cu4 N15B 83.7(6) . . ?
N15A Cu4 O2 98.4(5) . . ?
N10B Cu4 O2 96.7(6) . . ?
N11A Cu4 O2 94.3(5) . . ?
N14A Cu4 O2 96.4(5) . . ?
N11B Cu4 O2 93.2(4) . . ?
N14B Cu4 O2 93.7(4) . . ?
N15B Cu4 O2 90.3(4) . . ?
N15A Cu4 N10A 171.1(8) . . ?
N11A Cu4 N10A 84.8(8) . . ?
N14A Cu4 N10A 82.0(8) . . ?
O2 Cu4 N10A 90.5(6) . . ?
Cu2 O1 Cu2 180.00(4) 3_766 . ?
Cu2 O1 Cu1 90.90(3) 3_766 . ?
Cu2 O1 Cu1 89.10(3) . . ?
Cu2 O1 Cu1 89.10(3) 3_766 3_766 ?
Cu2 O1 Cu1 90.90(3) . 3_766 ?
Cu1 O1 Cu1 180.0 . 3_766 ?
Cu4 O2 Cu4 180.00(5) . 3_656 ?
Cu4 O2 Cu3 90.76(4) . 3_656 ?
Cu4 O2 Cu3 89.24(4) 3_656 3_656 ?
Cu4 O2 Cu3 89.24(4) . . ?
Cu4 O2 Cu3 90.76(4) 3_656 . ?
Cu3 O2 Cu3 180.0 3_656 . ?
N2 N1 C1 108.6(7) . . ?
N2 N1 Cu1 114.8(4) . . ?
C1 N1 Cu1 136.4(6) . . ?
N1 N2 C3 108.2(6) . . ?
N1 N2 Cu2 120.2(4) . . ?
C3 N2 Cu2 131.6(6) . . ?
C6 N3 N4 107.7(6) . . ?
C6 N3 Cu2 136.2(6) . . ?
N4 N3 Cu2 116.0(4) . . ?
C8 N4 N3 107.1(6) . . ?
C8 N4 Cu1 134.1(6) . 3_766 ?
N3 N4 Cu1 118.5(4) . 3_766 ?
C9 N5 N6 107.8(7) . . ?
C9 N5 Cu1 132.4(6) . . ?
N6 N5 Cu1 119.5(5) . . ?
C11 N6 N5 108.0(6) . . ?
C11 N6 Cu2 137.8(5) . . ?
N5 N6 Cu2 114.1(5) . . ?
N8 N7 C14 108.0(6) . . ?
N8 N7 Cu2 122.8(5) . . ?
C14 N7 Cu2 128.4(5) . . ?
C16 N8 N7 108.6(7) . . ?
C16 N8 Cu1 138.2(6) . 3_766 ?
N7 N8 Cu1 113.2(4) . 3_766 ?
C37 N17 C33 111.1(7) . . ?
C37 N17 C41 112.0(7) . . ?
C33 N17 C41 106.7(6) . . ?
C37 N17 C45 106.7(6) . . ?
C33 N17 C45 109.7(7) . . ?
C41 N17 C45 110.6(6) . . ?
N1 C1 C2 109.2(8) . . ?
N1 C1 H1 125.4 . . ?
C2 C1 H1 125.4 . . ?
C3 C2 C1 104.8(7) . . ?
C3 C2 H2 127.6 . . ?
C1 C2 H2 127.6 . . ?
N2 C3 C2 109.2(7) . . ?
N2 C3 C4 121.2(8) . . ?
C2 C3 C4 129.6(8) . . ?
C5 C4 C3 124.0(10) . . ?
C5 C4 H4A 106.3 . . ?
C3 C4 H4A 106.3 . . ?
C5 C4 H4B 106.3 . . ?
C3 C4 H4B 106.3 . . ?
H4A C4 H4B 106.4 . . ?
C4 C5 C6 125.3(10) . . ?
C4 C5 H5A 106.0 . . ?
C6 C5 H5A 106.0 . . ?
C4 C5 H5B 106.0 . . ?
C6 C5 H5B 106.0 . . ?
H5A C5 H5B 106.3 . . ?
N3 C6 C7 109.3(8) . . ?
N3 C6 C5 124.0(9) . . ?
C7 C6 C5 126.4(9) . . ?
C6 C7 C8 104.8(7) . . ?
C6 C7 H7 127.6 . . ?
C8 C7 H7 127.6 . . ?
N4 C8 C7 111.0(8) . . ?
N4 C8 H8 124.5 . . ?
C7 C8 H8 124.5 . . ?
N5 C9 C10 109.8(7) . . ?
N5 C9 H9 125.1 . . ?
C10 C9 H9 125.1 . . ?
C9 C10 C11 105.8(7) . . ?
C9 C10 H10 127.1 . . ?
C11 C10 H10 127.1 . . ?
N6 C11 C10 108.5(7) . . ?
N6 C11 C12 124.9(7) . . ?
C10 C11 C12 126.5(7) . . ?
C11 C12 C13 119.1(7) . . ?
C11 C12 H12A 107.5 . . ?
C13 C12 H12A 107.5 . . ?
C11 C12 H12B 107.5 . . ?
C13 C12 H12B 107.5 . . ?
H12A C12 H12B 107.0 . . ?
C14 C13 C12 113.9(7) . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
N7 C14 C15 109.1(8) . . ?
N7 C14 C13 118.0(7) . . ?
C15 C14 C13 132.9(8) . . ?
C14 C15 C16 105.1(7) . . ?
C14 C15 H15 127.4 . . ?
C16 C15 H15 127.4 . . ?
N8 C16 C15 109.2(8) . . ?
N8 C16 H16 125.4 . . ?
C15 C16 H16 125.4 . . ?
N9A C17A C18A 107(2) . . ?
N9A C17A H17A 126.5 . . ?
C18A C17A H17A 126.5 . . ?
C17A C18A C19A 108(2) . . ?
C17A C18A H18A 125.9 . . ?
C19A C18A H18A 125.9 . . ?
N10A C19A C18A 106(2) . . ?
N10A C19A C20A 130(3) . . ?
C18A C19A C20A 123(2) . . ?
C21A C20A C19A 116(3) . . ?
C21A C20A H20A 108.4 . . ?
C19A C20A H20A 108.4 . . ?
C21A C20A H20B 108.4 . . ?
C19A C20A H20B 108.4 . . ?
H20A C20A H20B 107.5 . . ?
N11A C22A C23A 111.1(19) . . ?
N11A C22A C21A 121.8(18) . . ?
C23A C22A C21A 127(2) . . ?
C20A C21A C22A 120(3) . . ?
C20A C21A H21A 107.4 . . ?
C22A C21A H21A 107.4 . . ?
C20A C21A H21B 107.4 . . ?
C22A C21A H21B 107.4 . . ?
H21A C21A H21B 106.9 . . ?
C24A C23A C22A 104.0(19) . . ?
C24A C23A H23A 128.0 . . ?
C22A C23A H23A 128.0 . . ?
C23A C24A N12A 109.2(17) . . ?
C23A C24A H24A 125.4 . . ?
N12A C24A H24A 125.4 . . ?
C17A N9A N10A 108.9(19) . . ?
C17A N9A Cu3 132.2(17) . . ?
N10A N9A Cu3 116.9(14) . . ?
C19A N10A N9A 109(2) . . ?
C19A N10A Cu4 138(2) . . ?
N9A N10A Cu4 113.1(15) . . ?
N12A N11A C22A 106.1(15) . . ?
N12A N11A Cu4 118.9(13) . . ?
C22A N11A Cu4 133.5(13) . . ?
N11A N12A C24A 109.5(17) . . ?
N11A N12A Cu3 114.9(12) . 3_656 ?
C24A N12A Cu3 135.3(15) . 3_656 ?
N13A C25A C26A 109.9(18) . . ?
N13A C25A H25A 125.1 . . ?
C26A C25A H25A 125.1 . . ?
C25A C26A C27A 103.7(17) . . ?
C25A C26A H26A 128.1 . . ?
C27A C26A H26A 128.1 . . ?
N14A C27A C26A 110.2(16) . . ?
N14A C27A C28A 117.9(15) . . ?
C26A C27A C28A 131.4(16) . . ?
C27A C28A C29A 114.9(16) . . ?
C27A C28A H28A 108.6 . . ?
C29A C28A H28A 108.6 . . ?
C27A C28A H28B 108.6 . . ?
C29A C28A H28B 108.6 . . ?
H28A C28A H28B 107.5 . . ?
C30A C29A C28A 104.7(16) . . ?
C30A C29A H29A 110.8 . . ?
C28A C29A H29A 110.8 . . ?
C30A C29A H29B 110.8 . . ?
C28A C29A H29B 110.8 . . ?
H29A C29A H29B 108.9 . . ?
C29A C30A N15A 137.1(16) . . ?
C29A C30A C31A 109.0(15) . . ?
N15A C30A C31A 110.7(16) . . ?
C32A C31A C30A 105.8(17) . . ?
C32A C31A H31A 127.1 . . ?
C30A C31A H31A 127.1 . . ?
N16A C32A C31A 106(2) . . ?
N16A C32A H32A 127.2 . . ?
C31A C32A H32A 127.2 . . ?
N14A N13A C25A 108.9(16) . . ?
N14A N13A Cu3 110.7(12) . . ?
C25A N13A Cu3 140.1(14) . . ?
N13A N14A C27A 107.3(15) . . ?
N13A N14A Cu4 124.8(13) . . ?
C27A N14A Cu4 125.0(13) . . ?
C30A N15A N16A 104.7(16) . . ?
C30A N15A Cu4 138.0(13) . . ?
N16A N15A Cu4 116.6(13) . . ?
C32A N16A N15A 113.0(19) . . ?
C32A N16A Cu3 127.4(17) . 3_656 ?
N15A N16A Cu3 119.6(13) . 3_656 ?
N9B C17B C18B 107(2) . . ?
N9B C17B H17B 126.3 . . ?
C18B C17B H17B 126.3 . . ?
C17B C18B C19B 105.7(17) . . ?
C17B C18B H18B 127.1 . . ?
C19B C18B H18B 127.1 . . ?
N10B C19B C18B 107.5(18) . . ?
N10B C19B C20B 127(2) . . ?
C18B C19B C20B 124.9(18) . . ?
C19B C20B C21B 116.6(16) . . ?
C19B C20B H20C 108.1 . . ?
C21B C20B H20C 108.1 . . ?
C19B C20B H20D 108.1 . . ?
C21B C20B H20D 108.1 . . ?
H20C C20B H20D 107.3 . . ?
C20B C21B C22B 116.8(15) . . ?
C20B C21B H21C 108.1 . . ?
C22B C21B H21C 108.1 . . ?
C20B C21B H21D 108.1 . . ?
C22B C21B H21D 108.1 . . ?
H21C C21B H21D 107.3 . . ?
C23B C22B N11B 106.7(19) . . ?
C23B C22B C21B 136(2) . . ?
N11B C22B C21B 117.3(16) . . ?
C22B C23B C24B 104.8(19) . . ?
C22B C23B H23B 127.6 . . ?
C24B C23B H23B 127.6 . . ?
N12B C24B C23B 110.7(18) . . ?
N12B C24B H24B 124.6 . . ?
C23B C24B H24B 124.6 . . ?
N10B N9B C17B 112(2) . . ?
N10B N9B Cu3 119.4(13) . . ?
C17B N9B Cu3 127.6(18) . . ?
N9B N10B C19B 107.0(19) . . ?
N9B N10B Cu4 115.3(14) . . ?
C19B N10B Cu4 137.4(16) . . ?
N12B N11B C22B 109.7(16) . . ?
N12B N11B Cu4 124.2(11) . . ?
C22B N11B Cu4 125.4(13) . . ?
C24B N12B N11B 108.0(17) . . ?
C24B N12B Cu3 139.4(16) . 3_656 ?
N11B N12B Cu3 112.6(12) . 3_656 ?
N13B C25B C26B 109.1(16) . . ?
N13B C25B H25B 125.5 . . ?
C26B C25B H25B 125.5 . . ?
C27B C26B C25B 105.4(15) . . ?
C27B C26B H26B 127.3 . . ?
C25B C26B H26B 127.3 . . ?
C26B C27B N14B 109.8(14) . . ?
C26B C27B C28B 123.3(16) . . ?
N14B C27B C28B 126.8(16) . . ?
C29B C28B C27B 124.5(19) . . ?
C29B C28B H28C 106.2 . . ?
C27B C28B H28C 106.2 . . ?
C29B C28B H28D 106.2 . . ?
C27B C28B H28D 106.2 . . ?
H28C C28B H28D 106.4 . . ?
C28B C29B C30B 102.3(17) . . ?
C28B C29B H29C 111.3 . . ?
C30B C29B H29C 111.3 . . ?
C28B C29B H29D 111.3 . . ?
C30B C29B H29D 111.3 . . ?
H29C C29B H29D 109.2 . . ?
C31B C30B N15B 106.9(17) . . ?
C31B C30B C29B 149.1(17) . . ?
N15B C30B C29B 101.6(17) . . ?
C30B C31B C32B 109(2) . . ?
C30B C31B H31B 125.7 . . ?
C32B C31B H31B 125.7 . . ?
N16B C32B C31B 110(2) . . ?
N16B C32B H32B 124.8 . . ?
C31B C32B H32B 124.8 . . ?
C25B N13B N14B 108.1(14) . . ?
C25B N13B Cu3 135.9(12) . . ?
N14B N13B Cu3 115.5(10) . . ?
C27B N14B N13B 107.1(13) . . ?
C27B N14B Cu4 136.5(11) . . ?
N13B N14B Cu4 115.7(10) . . ?
N16B N15B C30B 108.3(15) . . ?
N16B N15B Cu4 115.4(10) . . ?
C30B N15B Cu4 135.6(14) . . ?
C32B N16B N15B 105.8(14) . . ?
C32B N16B Cu3 137.4(14) . 3_656 ?
N15B N16B Cu3 116.5(11) . 3_656 ?
C34 C33 N17 115.6(7) . . ?
C34 C33 H33A 108.4 . . ?
N17 C33 H33A 108.4 . . ?
C34 C33 H33B 108.4 . . ?
N17 C33 H33B 108.4 . . ?
H33A C33 H33B 107.4 . . ?
C33 C34 C35 111.5(8) . . ?
C33 C34 H34A 109.3 . . ?
C35 C34 H34A 109.3 . . ?
C33 C34 H34B 109.3 . . ?
C35 C34 H34B 109.3 . . ?
H34A C34 H34B 108.0 . . ?
C36 C35 C34 114.3(8) . . ?
C36 C35 H35A 108.7 . . ?
C34 C35 H35A 108.7 . . ?
C36 C35 H35B 108.7 . . ?
C34 C35 H35B 108.7 . . ?
H35A C35 H35B 107.6 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N17 C37 C38 115.4(6) . . ?
N17 C37 H37A 108.4 . . ?
C38 C37 H37A 108.4 . . ?
N17 C37 H37B 108.4 . . ?
C38 C37 H37B 108.4 . . ?
H37A C37 H37B 107.5 . . ?
C39 C38 C37 112.9(7) . . ?
C39 C38 H38A 109.0 . . ?
C37 C38 H38A 109.0 . . ?
C39 C38 H38B 109.0 . . ?
C37 C38 H38B 109.0 . . ?
H38A C38 H38B 107.8 . . ?
C38 C39 C40 112.4(8) . . ?
C38 C39 H39A 109.1 . . ?
C40 C39 H39A 109.1 . . ?
C38 C39 H39B 109.1 . . ?
C40 C39 H39B 109.1 . . ?
H39A C39 H39B 107.9 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C42 C41 N17 115.8(6) . . ?
C42 C41 H41A 108.3 . . ?
N17 C41 H41A 108.3 . . ?
C42 C41 H41B 108.3 . . ?
N17 C41 H41B 108.3 . . ?
H41A C41 H41B 107.4 . . ?
C43 C42 C41 114.3(7) . . ?
C43 C42 H42A 108.7 . . ?
C41 C42 H42A 108.7 . . ?
C43 C42 H42B 108.7 . . ?
C41 C42 H42B 108.7 . . ?
H42A C42 H42B 107.6 . . ?
C42 C43 C44 115.5(8) . . ?
C42 C43 H43A 108.4 . . ?
C44 C43 H43A 108.4 . . ?
C42 C43 H43B 108.4 . . ?
C44 C43 H43B 108.4 . . ?
H43A C43 H43B 107.5 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C46A C45 N17 116.7(9) . . ?
N17 C45 C46B 112.4(9) . . ?
C46A C45 H45A 108.1 . . ?
N17 C45 H45A 108.1 . . ?
C46A C45 H45B 108.1 . . ?
N17 C45 H45B 108.1 . . ?
H45A C45 H45B 107.3 . . ?
C45 C46A C47A 103.7(12) . . ?
C45 C46A H46A 111.0 . . ?
C47A C46A H46A 111.0 . . ?
C45 C46A H46B 111.0 . . ?
C47A C46A H46B 111.0 . . ?
H46A C46A H46B 109.0 . . ?
C46A C47A C48A 103.4(12) . . ?
C46A C47A H47A 111.1 . . ?
C48A C47A H47A 111.1 . . ?
C46A C47A H47B 111.1 . . ?
C48A C47A H47B 111.1 . . ?
H47A C47A H47B 109.1 . . ?
C47A C48A H48A 109.5 . . ?
C47A C48A H48B 109.5 . . ?
H48A C48A H48B 109.5 . . ?
C47A C48A H48C 109.5 . . ?
H48A C48A H48C 109.5 . . ?
H48B C48A H48C 109.5 . . ?
C47B C46B C45 123.9(16) . . ?
C47B C46B H46C 106.4 . . ?
C45 C46B H46C 106.4 . . ?
C47B C46B H46D 106.4 . . ?
C45 C46B H46D 106.4 . . ?
H46C C46B H46D 106.4 . . ?
C48B C47B C46B 112.8(19) . . ?
C48B C47B H47C 109.0 . . ?
C46B C47B H47C 109.0 . . ?
C48B C47B H47D 109.0 . . ?
C46B C47B H47D 109.0 . . ?
H47C C47B H47D 107.8 . . ?
C47B C48B H48D 109.5 . . ?
C47B C48B H48E 109.5 . . ?
H48D C48B H48E 109.5 . . ?
C47B C48B H48F 109.5 . . ?
H48D C48B H48F 109.5 . . ?
H48E C48B H48F 109.5 . . ?

_refine_diff_density_max         1.689
_refine_diff_density_min         -0.973
_refine_diff_density_rms         0.117

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane, diethyl ether'
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1508665'
_audit_update_record             
;
2016-10-06 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H20 N2 O2'
_chemical_formula_weight         224.30

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   16.6684(3)
_cell_length_b                   5.43570(10)
_cell_length_c                   14.3613(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.3620(10)
_cell_angle_gamma                90
_cell_volume                     1287.36(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    6922
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      32.14

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7008
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18079
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.470
_diffrn_reflns_theta_max         32.576
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2348
_reflns_number_gt                1870
_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-2014 (Sheldrick 2014)'
_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)+(0.1015P)²+0.3317P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2348
_refine_ls_number_parameters     75
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.1821
_refine_ls_wR_factor_gt          0.1681
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
O1 O 0.35734(5) 0.1425(2) 0.47604(7) 0.0658(3) Uani 1 1 d . . . . .
N1 N 0.31834(5) 0.68947(17) 0.66467(6) 0.0439(2) Uani 1 1 d . . . . .
C3 C 0.33521(6) 0.51310(19) 0.60585(6) 0.0383(2) Uani 1 1 d . . . . .
H3 H 0.2930 0.4665 0.5595 0.046 Uiso 1 1 calc R U . . .
C5 C 0.41399(6) 0.2078(2) 0.53538(7) 0.0414(2) Uani 1 1 d . . . . .
C4 C 0.40701(6) 0.3931(2) 0.60561(7) 0.0435(3) Uani 1 1 d . . . . .
H4 H 0.4513 0.4306 0.6506 0.052 Uiso 1 1 calc R U . . .
C6 C 0.49760(6) 0.0963(3) 0.53679(8) 0.0517(3) Uani 1 1 d . . . . .
H6A H 0.5355 0.2269 0.5283 0.062 Uiso 1 1 calc R U . . .
H6B H 0.5146 0.0239 0.5982 0.062 Uiso 1 1 calc R U . . .
C1 C 0.24204(8) 0.8208(2) 0.64888(9) 0.0536(3) Uani 1 1 d . . . . .
H1A H 0.2512 0.9855 0.6287 0.080 Uiso 1 1 calc R U . . .
H1B H 0.2189 0.8259 0.7063 0.080 Uiso 1 1 calc R U . . .
H1C H 0.2055 0.7381 0.6012 0.080 Uiso 1 1 calc R U . . .
C2 C 0.37880(8) 0.7785(3) 0.73987(10) 0.0609(4) Uani 1 1 d . . . . .
H2A H 0.4120 0.6437 0.7658 0.091 Uiso 1 1 calc R U . . .
H2B H 0.3523 0.8511 0.7882 0.091 Uiso 1 1 calc R U . . .
H2C H 0.4121 0.8995 0.7154 0.091 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
O1 C5 1.2288(13) . ?
N1 C3 1.3345(13) . ?
N1 C1 1.4472(14) . ?
N1 C2 1.4490(15) . ?
C3 C4 1.3634(13) . ?
C3 H3 0.9300 . ?
C5 C4 1.4420(15) . ?
C5 C6 1.5173(14) . ?
C4 H4 0.9300 . ?
C6 C6 1.498(2) 5_656 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 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
C3 N1 C1 121.09(9) . . ?
C3 N1 C2 121.60(10) . . ?
C1 N1 C2 116.89(10) . . ?
N1 C3 C4 127.66(10) . . ?
N1 C3 H3 116.2 . . ?
C4 C3 H3 116.2 . . ?
O1 C5 C4 123.71(9) . . ?
O1 C5 C6 120.36(10) . . ?
C4 C5 C6 115.92(9) . . ?
C3 C4 C5 119.73(9) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C6 C5 114.40(11) 5_656 . ?
C6 C6 H6A 108.7 5_656 . ?
C5 C6 H6A 108.7 . . ?
C6 C6 H6B 108.7 5_656 . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.051

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate, hexanes'
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1519412'
_audit_update_record             
;
2016-11-26 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C41 H43 Cu4 N15 O8'
_chemical_formula_weight         1128.06

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   11.0383(2)
_cell_length_b                   19.3794(5)
_cell_length_c                   25.1577(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5381.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9863
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      18.93

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             2296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    1.618
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5482
_exptl_absorpt_correction_T_max  0.7443
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   'Bruker, 2014'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53884
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.326
_diffrn_reflns_theta_max         18.938
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.453
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.453
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.440
_reflns_number_total             4281
_reflns_number_gt                3994
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    0.424

_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-2014 (Sheldrick 2014)'
_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)+(0.1112P)²+13.4335P] 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_abs_structure_details 
;
 Flack x determined using 1643 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4281
_refine_ls_number_parameters     619
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1641
_refine_ls_wR_factor_gt          0.1585
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.156
_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 0.62450(19) 0.66624(11) 0.62192(8) 0.0457(7) Uani 1 1 d D . . . .
Cu2 Cu 0.5218(2) 0.52709(12) 0.68467(10) 0.0494(8) Uani 1 1 d D . . . .
Cu3 Cu 0.33735(18) 0.63023(11) 0.64735(9) 0.0448(7) Uani 1 1 d D . . . .
Cu4 Cu 0.3072(2) 0.56776(13) 0.76940(9) 0.0572(8) Uani 1 1 d . . . . .
O1 O 0.5028(10) 0.5944(6) 0.6264(4) 0.043(3) Uani 1 1 d D . . . .
H1O H 0.493(3) 0.5717(16) 0.5945(9) 0.052 Uiso 1 1 d D U . . .
O2 O 0.3448(10) 0.5497(6) 0.6939(5) 0.045(3) Uani 1 1 d D . . . .
H2O H 0.306(15) 0.521(7) 0.677(6) 0.055 Uiso 1 1 d D U . . .
O3 O 0.6577(17) 0.5575(10) 0.4625(8) 0.114(7) Uani 1 1 d . . . . .
O4 O 0.6910(14) 0.6026(9) 0.5384(6) 0.077(5) Uani 1 1 d . . . . .
O5 O 0.5196(16) 0.5583(9) 0.5212(5) 0.076(4) Uani 1 1 d . . . . .
O6 O 0.215(2) 0.4325(11) 0.6816(8) 0.124(8) Uani 1 1 d . . . . .
O7 O 0.1366(14) 0.4737(10) 0.7529(8) 0.094(5) Uani 1 1 d . . . . .
O8 O 0.114(2) 0.3658(10) 0.7374(8) 0.122(7) Uani 1 1 d . . . . .
N1 N 0.7286(13) 0.6145(8) 0.6695(6) 0.046(4) Uani 1 1 d . . . . .
N2 N 0.6988(13) 0.5505(9) 0.6893(6) 0.055(4) Uani 1 1 d . . . . .
N3 N 0.5116(16) 0.4771(9) 0.7508(7) 0.060(5) Uani 1 1 d . . . . .
N4 N 0.4228(15) 0.4932(9) 0.7872(7) 0.059(5) Uani 1 1 d . . . . .
N5 N 0.2082(13) 0.6474(8) 0.7460(7) 0.049(4) Uani 1 1 d . . . . .
N6 N 0.2187(13) 0.6760(9) 0.6967(6) 0.048(4) Uani 1 1 d . . . . .
N7 N 0.3772(15) 0.7109(8) 0.6073(6) 0.048(4) Uani 1 1 d . . . . .
N8 N 0.4969(13) 0.7260(7) 0.5947(6) 0.044(4) Uani 1 1 d . . . . .
N9 N 0.7476(13) 0.7428(8) 0.6105(7) 0.049(4) Uani 1 1 d . . . . .
N10 N 0.5335(18) 0.4399(10) 0.6246(8) 0.077(5) Uani 1 1 d D . . . .
N11 N 0.241(2) 0.5720(11) 0.8453(8) 0.080(6) Uani 1 1 d D . . . .
N12 N 0.2002(15) 0.5780(8) 0.5908(8) 0.053(4) Uani 1 1 d . . . . .
N13 N 0.6251(19) 0.5736(10) 0.5072(8) 0.062(5) Uani 1 1 d . . . . .
N14 N 0.1511(19) 0.4229(11) 0.7258(11) 0.080(6) Uani 1 1 d . . . . .
N15 N 0.488(2) 0.6497(11) 0.7794(9) 0.098(7) Uani 1 1 d . . . . .
C1 C 0.8384(19) 0.6257(11) 0.6873(8) 0.059(5) Uani 1 1 d . . . . .
H1 H 0.8822 0.6656 0.6799 0.071 Uiso 1 1 calc R U . . .
C2 C 0.882(2) 0.5738(15) 0.7173(9) 0.077(7) Uani 1 1 d . . . . .
H2 H 0.9569 0.5713 0.7336 0.093 Uiso 1 1 calc R U . . .
C3 C 0.7908(19) 0.5251(13) 0.7186(8) 0.068(7) Uani 1 1 d . . . . .
C4 C 0.800(2) 0.4575(13) 0.7470(11) 0.096(9) Uani 1 1 d . . . . .
H4A H 0.8115 0.4670 0.7845 0.116 Uiso 1 1 calc R U . . .
H4B H 0.8732 0.4346 0.7345 0.116 Uiso 1 1 calc R U . . .
C5 C 0.694(2) 0.4065(10) 0.7413(10) 0.075(7) Uani 1 1 d . . . . .
H5A H 0.6724 0.4024 0.7041 0.089 Uiso 1 1 calc R U . . .
H5B H 0.7193 0.3614 0.7538 0.089 Uiso 1 1 calc R U . . .
C6 C 0.5884(18) 0.4292(11) 0.7716(9) 0.059(6) Uani 1 1 d . . . . .
C7 C 0.545(2) 0.4114(13) 0.8203(11) 0.088(8) Uani 1 1 d . . . . .
H7 H 0.5771 0.3786 0.8434 0.105 Uiso 1 1 calc R U . . .
C8 C 0.444(2) 0.4520(13) 0.8283(9) 0.076(7) Uani 1 1 d . . . . .
H8 H 0.3972 0.4508 0.8589 0.091 Uiso 1 1 calc R U . . .
C9 C 0.129(2) 0.6852(13) 0.7739(10) 0.075(7) Uani 1 1 d . . . . .
H9 H 0.1030 0.6760 0.8082 0.090 Uiso 1 1 calc R U . . .
C10 C 0.0933(19) 0.7415(10) 0.7421(11) 0.068(7) Uani 1 1 d . . . . .
H10 H 0.0413 0.7772 0.7517 0.082 Uiso 1 1 calc R U . . .
C11 C 0.1502(17) 0.7330(11) 0.6943(9) 0.051(5) Uani 1 1 d . . . . .
C12 C 0.134(2) 0.7820(12) 0.6487(9) 0.081(7) Uani 1 1 d . . . . .
H12A H 0.0486 0.7941 0.6472 0.097 Uiso 1 1 calc R U . . .
H12B H 0.1780 0.8238 0.6572 0.097 Uiso 1 1 calc R U . . .
C13 C 0.1708(18) 0.7601(12) 0.5951(8) 0.063(6) Uani 1 1 d . . . . .
H13A H 0.1333 0.7904 0.5692 0.075 Uiso 1 1 calc R U . . .
H13B H 0.1408 0.7138 0.5887 0.075 Uiso 1 1 calc R U . . .
C14 C 0.305(2) 0.7608(12) 0.5867(8) 0.062(6) Uani 1 1 d . . . . .
C15 C 0.379(2) 0.8102(9) 0.5615(7) 0.053(5) Uani 1 1 d . . . . .
H15 H 0.3553 0.8502 0.5440 0.063 Uiso 1 1 calc R U . . .
C16 C 0.4918(19) 0.7868(11) 0.5682(7) 0.052(5) Uani 1 1 d . . . . .
H16 H 0.5601 0.8100 0.5559 0.062 Uiso 1 1 calc R U . . .
C17 C 0.7567(19) 0.7958(11) 0.6457(9) 0.063(6) Uani 1 1 d . . . . .
H17 H 0.7186 0.7935 0.6786 0.076 Uiso 1 1 calc R U . . .
C18 C 0.8247(19) 0.8540(9) 0.6313(9) 0.060(6) Uani 1 1 d . . . . .
H18 H 0.8308 0.8909 0.6548 0.072 Uiso 1 1 calc R U . . .
C19 C 0.8818(17) 0.8573(11) 0.5837(9) 0.057(5) Uani 1 1 d . . . . .
H19 H 0.9265 0.8962 0.5744 0.068 Uiso 1 1 calc R U . . .
C20 C 0.8726(17) 0.8021(13) 0.5489(8) 0.058(6) Uani 1 1 d . . . . .
H20 H 0.9104 0.8034 0.5158 0.070 Uiso 1 1 calc R U . . .
C21 C 0.8079(18) 0.7468(11) 0.5640(8) 0.053(5) Uani 1 1 d . . . . .
H21 H 0.8044 0.7092 0.5411 0.064 Uiso 1 1 calc R U . . .
C22 C 0.453(3) 0.3879(13) 0.6232(11) 0.109(9) Uani 1 1 d D . . . .
H22 H 0.3873 0.3915 0.6463 0.131 Uiso 1 1 calc R U . . .
C23 C 0.456(4) 0.3306(16) 0.5920(16) 0.26(4) Uani 1 1 d D . . . .
H23 H 0.3991 0.2954 0.5942 0.311 Uiso 1 1 calc R U . . .
C24 C 0.552(5) 0.330(3) 0.556(2) 0.30(5) Uani 1 1 d D . . . .
H24 H 0.5554 0.2937 0.5320 0.355 Uiso 1 1 calc R U . . .
C25 C 0.644(4) 0.379(2) 0.5550(14) 0.21(3) Uani 1 1 d D . . . .
H25 H 0.7106 0.3754 0.5327 0.252 Uiso 1 1 calc R U . . .
C26 C 0.627(2) 0.4348(15) 0.5898(11) 0.117(10) Uani 1 1 d D . . . .
H26 H 0.6834 0.4704 0.5890 0.140 Uiso 1 1 calc R U . . .
C27 C 0.307(3) 0.6030(17) 0.8823(13) 0.127(12) Uani 1 1 d D . . . .
H27 H 0.3818 0.6212 0.8721 0.152 Uiso 1 1 calc R U . . .
C28 C 0.273(4) 0.610(3) 0.9348(16) 0.178(18) Uani 1 1 d D . . . .
H28 H 0.3168 0.6332 0.9608 0.214 Uiso 1 1 calc R U . . .
C29 C 0.163(4) 0.577(2) 0.9430(14) 0.17(2) Uani 1 1 d D . . . .
H29 H 0.1357 0.5765 0.9780 0.203 Uiso 1 1 calc R U . . .
C30 C 0.088(4) 0.5454(18) 0.9069(16) 0.136(14) Uani 1 1 d D . . . .
H30 H 0.0127 0.5274 0.9155 0.163 Uiso 1 1 calc R U . . .
C31 C 0.136(3) 0.5429(13) 0.8582(11) 0.097(9) Uani 1 1 d D . . . .
H31 H 0.0930 0.5197 0.8318 0.116 Uiso 1 1 calc R U . . .
C32 C 0.216(2) 0.5745(11) 0.5406(12) 0.070(6) Uani 1 1 d . . . . .
H32 H 0.2926 0.5829 0.5266 0.084 Uiso 1 1 calc R U . . .
C33 C 0.117(3) 0.5579(13) 0.5050(9) 0.093(9) Uani 1 1 d . . . . .
H33 H 0.1283 0.5535 0.4685 0.111 Uiso 1 1 calc R U . . .
C34 C 0.005(2) 0.5489(13) 0.5289(18) 0.101(11) Uani 1 1 d . . . . .
H34 H -0.0635 0.5392 0.5084 0.121 Uiso 1 1 calc R U . . .
C35 C -0.004(3) 0.5544(16) 0.5814(14) 0.099(10) Uani 1 1 d . . . . .
H35 H -0.0779 0.5489 0.5986 0.119 Uiso 1 1 calc R U . . .
C36 C 0.093(2) 0.5676(13) 0.6078(9) 0.073(7) Uani 1 1 d . . . . .
H36 H 0.0830 0.5698 0.6445 0.088 Uiso 1 1 calc R U . . .
C37 C 0.486(3) 0.7172(17) 0.7654(11) 0.100(9) Uani 1 1 d . . . . .
H37 H 0.4143 0.7335 0.7503 0.120 Uiso 1 1 calc R U . . .
C38 C 0.574(4) 0.7617(15) 0.7709(14) 0.113(10) Uani 1 1 d . . . . .
H38 H 0.5637 0.8072 0.7601 0.135 Uiso 1 1 calc R U . . .
C39 C 0.682(4) 0.741(3) 0.7926(13) 0.128(13) Uani 1 1 d . . . . .
H39 H 0.7466 0.7718 0.7975 0.153 Uiso 1 1 calc R U . . .
C40 C 0.689(3) 0.674(2) 0.8062(11) 0.103(9) Uani 1 1 d . . . . .
H40 H 0.7615 0.6571 0.8197 0.123 Uiso 1 1 calc R U . . .
C41 C 0.592(3) 0.6315(13) 0.8007(11) 0.092(8) Uani 1 1 d . . . . .
H41 H 0.6001 0.5863 0.8127 0.110 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 O1 1.938(11) . ?
Cu1 N1 1.938(15) . ?
Cu1 N8 1.947(15) . ?
Cu1 N9 2.033(15) . ?
Cu2 N3 1.929(16) . ?
Cu2 O1 1.973(11) . ?
Cu2 N2 2.010(15) . ?
Cu2 O2 2.015(11) . ?
Cu2 N10 2.27(2) . ?
Cu2 Cu3 3.003(3) . ?
Cu3 N7 1.911(15) . ?
Cu3 O2 1.953(12) . ?
Cu3 N6 2.010(15) . ?
Cu3 O1 2.024(11) . ?
Cu3 N12 2.310(17) . ?
Cu4 N4 1.979(17) . ?
Cu4 O2 1.975(12) . ?
Cu4 N5 1.982(15) . ?
Cu4 N11 2.05(2) . ?
O1 H1O 0.92(2) . ?
O2 H2O 0.82(3) . ?
O3 N13 1.22(2) . ?
O4 N13 1.21(2) . ?
O5 N13 1.25(2) . ?
O6 N14 1.33(3) . ?
O7 N14 1.21(2) . ?
O8 N14 1.22(2) . ?
N1 C1 1.31(2) . ?
N1 N2 1.38(2) . ?
N2 C3 1.35(2) . ?
N3 C6 1.36(2) . ?
N3 N4 1.38(2) . ?
N4 C8 1.33(3) . ?
N5 C9 1.34(2) . ?
N5 N6 1.36(2) . ?
N6 C11 1.34(2) . ?
N7 C14 1.36(2) . ?
N7 N8 1.39(2) . ?
N8 C16 1.36(2) . ?
N9 C21 1.35(2) . ?
N9 C17 1.36(2) . ?
N10 C22 1.35(2) . ?
N10 C26 1.36(2) . ?
N11 C31 1.33(2) . ?
N11 C27 1.33(2) . ?
N12 C36 1.28(3) . ?
N12 C32 1.28(3) . ?
N15 C41 1.31(3) . ?
N15 C37 1.35(3) . ?
C1 C2 1.34(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.38(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.50(3) . ?
C4 C5 1.54(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.46(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.36(3) . ?
C7 C8 1.38(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.41(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.37(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.50(3) . ?
C12 C13 1.47(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.49(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.41(3) . ?
C15 C16 1.33(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.40(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.36(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.39(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.34(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.36(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.39(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.39(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.40(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.38(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.39(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.37(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.33(2) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 C33 1.45(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.39(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.33(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.28(3) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 C38 1.31(4) . ?
C37 H37 0.9300 . ?
C38 C39 1.37(5) . ?
C38 H38 0.9300 . ?
C39 C40 1.34(4) . ?
C39 H39 0.9300 . ?
C40 C41 1.36(4) . ?
C40 H40 0.9300 . ?
C41 H41 0.9300 . ?

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
O1 Cu1 N1 90.2(6) . . ?
O1 Cu1 N8 86.9(5) . . ?
N1 Cu1 N8 162.4(6) . . ?
O1 Cu1 N9 175.0(6) . . ?
N1 Cu1 N9 93.9(6) . . ?
N8 Cu1 N9 90.0(6) . . ?
N3 Cu2 O1 165.2(7) . . ?
N3 Cu2 N2 96.9(7) . . ?
O1 Cu2 N2 89.8(6) . . ?
N3 Cu2 O2 87.3(6) . . ?
O1 Cu2 O2 80.8(5) . . ?
N2 Cu2 O2 152.4(6) . . ?
N3 Cu2 N10 101.8(7) . . ?
O1 Cu2 N10 90.2(6) . . ?
N2 Cu2 N10 98.7(7) . . ?
O2 Cu2 N10 107.1(6) . . ?
N3 Cu2 Cu3 124.4(6) . . ?
O1 Cu2 Cu3 41.9(3) . . ?
N2 Cu2 Cu3 121.8(5) . . ?
O2 Cu2 Cu3 40.0(3) . . ?
N10 Cu2 Cu3 109.0(4) . . ?
N7 Cu3 O2 163.7(6) . . ?
N7 Cu3 N6 96.6(7) . . ?
O2 Cu3 N6 90.5(6) . . ?
N7 Cu3 O1 86.3(6) . . ?
O2 Cu3 O1 81.0(5) . . ?
N6 Cu3 O1 154.1(5) . . ?
N7 Cu3 N12 100.7(7) . . ?
O2 Cu3 N12 92.7(6) . . ?
N6 Cu3 N12 98.4(6) . . ?
O1 Cu3 N12 106.3(6) . . ?
N7 Cu3 Cu2 123.6(5) . . ?
O2 Cu3 Cu2 41.6(3) . . ?
N6 Cu3 Cu2 122.8(5) . . ?
O1 Cu3 Cu2 40.7(3) . . ?
N12 Cu3 Cu2 110.2(4) . . ?
N4 Cu4 O2 87.3(6) . . ?
N4 Cu4 N5 172.7(7) . . ?
O2 Cu4 N5 88.2(6) . . ?
N4 Cu4 N11 92.8(8) . . ?
O2 Cu4 N11 168.3(8) . . ?
N5 Cu4 N11 92.8(7) . . ?
Cu1 O1 Cu2 116.4(6) . . ?
Cu1 O1 Cu3 113.2(5) . . ?
Cu2 O1 Cu3 97.4(5) . . ?
Cu1 O1 H1O 112(2) . . ?
Cu2 O1 H1O 110(2) . . ?
Cu3 O1 H1O 107(2) . . ?
Cu3 O2 Cu4 115.2(6) . . ?
Cu3 O2 Cu2 98.4(5) . . ?
Cu4 O2 Cu2 110.7(5) . . ?
Cu3 O2 H2O 101(10) . . ?
Cu4 O2 H2O 121(10) . . ?
Cu2 O2 H2O 107(10) . . ?
C1 N1 N2 104.2(15) . . ?
C1 N1 Cu1 132.3(15) . . ?
N2 N1 Cu1 123.3(12) . . ?
C3 N2 N1 110.4(15) . . ?
C3 N2 Cu2 133.0(15) . . ?
N1 N2 Cu2 114.5(11) . . ?
C6 N3 N4 110.0(15) . . ?
C6 N3 Cu2 129.6(15) . . ?
N4 N3 Cu2 120.1(13) . . ?
C8 N4 N3 104.7(16) . . ?
C8 N4 Cu4 136.9(16) . . ?
N3 N4 Cu4 118.3(12) . . ?
C9 N5 N6 108.1(16) . . ?
C9 N5 Cu4 129.1(16) . . ?
N6 N5 Cu4 122.7(13) . . ?
C11 N6 N5 109.1(15) . . ?
C11 N6 Cu3 134.7(14) . . ?
N5 N6 Cu3 116.0(13) . . ?
C14 N7 N8 108.9(15) . . ?
C14 N7 Cu3 130.4(15) . . ?
N8 N7 Cu3 120.8(12) . . ?
C16 N8 N7 104.8(14) . . ?
C16 N8 Cu1 136.1(14) . . ?
N7 N8 Cu1 118.8(11) . . ?
C21 N9 C17 119.1(17) . . ?
C21 N9 Cu1 119.6(15) . . ?
C17 N9 Cu1 120.5(14) . . ?
C22 N10 C26 116(2) . . ?
C22 N10 Cu2 122.5(17) . . ?
C26 N10 Cu2 121.8(19) . . ?
C31 N11 C27 120(2) . . ?
C31 N11 Cu4 122(2) . . ?
C27 N11 Cu4 118(2) . . ?
C36 N12 C32 116.7(18) . . ?
C36 N12 Cu3 118.2(16) . . ?
C32 N12 Cu3 122.9(15) . . ?
O4 N13 O3 122.7(19) . . ?
O4 N13 O5 119.1(19) . . ?
O3 N13 O5 118(2) . . ?
O7 N14 O8 124(3) . . ?
O7 N14 O6 115(2) . . ?
O8 N14 O6 121(2) . . ?
C41 N15 C37 113(2) . . ?
N1 C1 C2 113.3(19) . . ?
N1 C1 H1 123.4 . . ?
C2 C1 H1 123.4 . . ?
C1 C2 C3 105.6(18) . . ?
C1 C2 H2 127.2 . . ?
C3 C2 H2 127.2 . . ?
N2 C3 C2 106.5(19) . . ?
N2 C3 C4 129(2) . . ?
C2 C3 C4 124(2) . . ?
C3 C4 C5 117.7(19) . . ?
C3 C4 H4A 107.9 . . ?
C5 C4 H4A 107.9 . . ?
C3 C4 H4B 107.9 . . ?
C5 C4 H4B 107.9 . . ?
H4A C4 H4B 107.2 . . ?
C6 C5 C4 112(2) . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C7 C6 N3 107.5(18) . . ?
C7 C6 C5 132(2) . . ?
N3 C6 C5 120.1(19) . . ?
C6 C7 C8 105.7(19) . . ?
C6 C7 H7 127.2 . . ?
C8 C7 H7 127.2 . . ?
N4 C8 C7 112(2) . . ?
N4 C8 H8 124.0 . . ?
C7 C8 H8 124.0 . . ?
N5 C9 C10 108(2) . . ?
N5 C9 H9 125.9 . . ?
C10 C9 H9 125.9 . . ?
C11 C10 C9 105.9(17) . . ?
C11 C10 H10 127.0 . . ?
C9 C10 H10 127.0 . . ?
N6 C11 C10 108.7(18) . . ?
N6 C11 C12 129(2) . . ?
C10 C11 C12 123(2) . . ?
C13 C12 C11 119.0(19) . . ?
C13 C12 H12A 107.6 . . ?
C11 C12 H12A 107.6 . . ?
C13 C12 H12B 107.6 . . ?
C11 C12 H12B 107.6 . . ?
H12A C12 H12B 107.0 . . ?
C12 C13 C14 113.6(18) . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
N7 C14 C15 108.1(17) . . ?
N7 C14 C13 122(2) . . ?
C15 C14 C13 130(2) . . ?
C16 C15 C14 104.8(17) . . ?
C16 C15 H15 127.6 . . ?
C14 C15 H15 127.6 . . ?
C15 C16 N8 113.4(18) . . ?
C15 C16 H16 123.3 . . ?
N8 C16 H16 123.3 . . ?
N9 C17 C18 118.6(18) . . ?
N9 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C19 C18 C17 121.0(18) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 119.2(18) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C21 C20 C19 118.5(19) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
N9 C21 C20 123.6(19) . . ?
N9 C21 H21 118.2 . . ?
C20 C21 H21 118.2 . . ?
N10 C22 C23 127(3) . . ?
N10 C22 H22 116.3 . . ?
C23 C22 H22 116.3 . . ?
C22 C23 C24 114(4) . . ?
C22 C23 H23 123.1 . . ?
C24 C23 H23 123.1 . . ?
C23 C24 C25 124(5) . . ?
C23 C24 H24 117.9 . . ?
C25 C24 H24 117.9 . . ?
C24 C25 C26 115(4) . . ?
C24 C25 H25 122.7 . . ?
C26 C25 H25 122.7 . . ?
N10 C26 C25 124(3) . . ?
N10 C26 H26 118.0 . . ?
C25 C26 H26 118.0 . . ?
N11 C27 C28 124(3) . . ?
N11 C27 H27 117.9 . . ?
C28 C27 H27 117.9 . . ?
C29 C28 C27 110(4) . . ?
C29 C28 H28 125.1 . . ?
C27 C28 H28 125.1 . . ?
C30 C29 C28 129(4) . . ?
C30 C29 H29 115.4 . . ?
C28 C29 H29 115.4 . . ?
C31 C30 C29 113(3) . . ?
C31 C30 H30 123.5 . . ?
C29 C30 H30 123.5 . . ?
C30 C31 N11 123(3) . . ?
C30 C31 H31 118.3 . . ?
N11 C31 H31 118.3 . . ?
N12 C32 C33 121(2) . . ?
N12 C32 H32 119.3 . . ?
C33 C32 H32 119.3 . . ?
C34 C33 C32 116(2) . . ?
C34 C33 H33 122.1 . . ?
C32 C33 H33 122.1 . . ?
C35 C34 C33 119(3) . . ?
C35 C34 H34 120.6 . . ?
C33 C34 H34 120.6 . . ?
C36 C35 C34 118(3) . . ?
C36 C35 H35 120.9 . . ?
C34 C35 H35 120.9 . . ?
C35 C36 N12 129(2) . . ?
C35 C36 H36 115.4 . . ?
N12 C36 H36 115.4 . . ?
C38 C37 N15 126(3) . . ?
C38 C37 H37 116.8 . . ?
N15 C37 H37 116.8 . . ?
C37 C38 C39 120(3) . . ?
C37 C38 H38 119.9 . . ?
C39 C38 H38 119.9 . . ?
C40 C39 C38 115(3) . . ?
C40 C39 H39 122.3 . . ?
C38 C39 H39 122.3 . . ?
C39 C40 C41 121(3) . . ?
C39 C40 H40 119.4 . . ?
C41 C40 H40 119.4 . . ?
N15 C41 C40 124(3) . . ?
N15 C41 H41 117.9 . . ?
C40 C41 H41 117.9 . . ?

_refine_diff_density_max         1.043
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.143

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pyridine, diisopropyl ether'
