# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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 1056081'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H13 Cu2.50 N7'
_chemical_formula_weight         426.15

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   14.4313(5)
_cell_length_b                   13.2244(6)
_cell_length_c                   7.5812(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.883(3)
_cell_angle_gamma                90.00
_cell_volume                     1443.51(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3808
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      28.30

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.961
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             850
_exptl_absorpt_coefficient_mu    3.670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4056
_exptl_absorpt_correction_T_max  0.8378
_exptl_absorpt_process_details   'sadabs v2008/1(bruker axs, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14125
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_sigmaI/netI    0.0593
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         28.30
_reflns_number_total             3588
_reflns_number_gt                2139
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0328P)²+0.8996P] 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         3588
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0761
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.93405(3) 0.99999(4) 0.37824(5) 0.01338(11) Uani 1 1 d . . .
Cu2 Cu 0.66560(3) 0.49866(4) 0.42392(5) 0.01561(11) Uani 1 1 d . . .
Cu3 Cu 1.0000 0.5000 0.5000 0.01953(15) Uani 1 2 d S . .
N1 N 0.6929(2) 0.6544(2) 0.3592(4) 0.0147(7) Uani 1 1 d . . .
N2 N 0.9599(2) 0.8622(2) 0.3481(4) 0.0124(6) Uani 1 1 d . . .
N3 N 1.0863(2) 0.8645(2) 0.5579(4) 0.0120(6) Uani 1 1 d . . .
N4 N 1.3361(2) 0.9269(2) 0.3276(4) 0.0124(6) Uani 1 1 d . . .
N5 N 0.7937(2) 0.4687(2) 0.5054(4) 0.0192(7) Uani 1 1 d . . .
N6 N 0.8745(3) 0.4739(3) 0.5086(5) 0.0257(8) Uani 1 1 d . . .
N7 N 0.5400(2) 0.4983(3) 0.4889(4) 0.0224(7) Uani 1 1 d . . .
C1 C 0.8070(2) 0.7783(3) 0.2868(5) 0.0117(7) Uani 1 1 d . . .
C2 C 0.7755(2) 0.6804(3) 0.3020(5) 0.0135(8) Uani 1 1 d . . .
H2A H 0.8145 0.6285 0.2701 0.016 Uiso 1 1 calc R . .
C3 C 0.6370(2) 0.7307(3) 0.4031(5) 0.0157(8) Uani 1 1 d . . .
H3A H 0.5793 0.7152 0.4437 0.019 Uiso 1 1 calc R . .
C4 C 0.6620(3) 0.8306(3) 0.3901(5) 0.0192(9) Uani 1 1 d . . .
H4A H 0.6215 0.8814 0.4207 0.023 Uiso 1 1 calc R . .
C5 C 0.7476(3) 0.8550(3) 0.3313(5) 0.0165(8) Uani 1 1 d . . .
H5A H 0.7652 0.9223 0.3217 0.020 Uiso 1 1 calc R . .
C6 C 0.9029(2) 0.7974(3) 0.2263(5) 0.0135(8) Uani 1 1 d . . .
H6A H 0.9342 0.7331 0.2143 0.016 Uiso 1 1 calc R . .
H6B H 0.8972 0.8291 0.1107 0.016 Uiso 1 1 calc R . .
C7 C 1.0312(2) 0.8191(3) 0.4367(5) 0.0126(7) Uani 1 1 d . . .
H7A H 1.0435 0.7517 0.4119 0.015 Uiso 1 1 calc R . .
C8 C 1.1677(2) 0.8097(3) 0.6290(5) 0.0138(8) Uani 1 1 d . . .
H8A H 1.1601 0.7386 0.5998 0.017 Uiso 1 1 calc R . .
H8B H 1.1717 0.8156 0.7568 0.017 Uiso 1 1 calc R . .
C9 C 1.2577(2) 0.8470(3) 0.5603(5) 0.0127(7) Uani 1 1 d . . .
C10 C 1.2583(2) 0.8963(3) 0.4001(5) 0.0135(8) Uani 1 1 d . . .
H10A H 1.2015 0.9092 0.3385 0.016 Uiso 1 1 calc R . .
C11 C 1.4168(3) 0.9093(3) 0.4188(5) 0.0185(8) Uani 1 1 d . . .
H11A H 1.4714 0.9287 0.3694 0.022 Uiso 1 1 calc R . .
C12 C 1.4232(3) 0.8637(3) 0.5827(5) 0.0208(9) Uani 1 1 d . . .
H12A H 1.4807 0.8547 0.6439 0.025 Uiso 1 1 calc R . .
C13 C 1.3425(3) 0.8313(3) 0.6549(5) 0.0187(9) Uani 1 1 d . . .
H13A H 1.3450 0.7997 0.7647 0.022 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.877(3) . ?
Cu1 N3 1.884(3) 3_776 ?
Cu1 Cu1 2.5605(8) 3_776 ?
Cu2 N7 1.911(3) . ?
Cu2 N5 1.949(3) . ?
Cu2 N4 2.128(3) 2_745 ?
Cu2 N1 2.160(3) . ?
Cu3 N6 1.849(4) 3_766 ?
Cu3 N6 1.849(4) . ?
N1 C2 1.341(4) . ?
N1 C3 1.347(5) . ?
N2 C7 1.320(5) . ?
N2 C6 1.470(4) . ?
N3 C7 1.318(5) . ?
N3 C8 1.452(4) . ?
N3 Cu1 1.884(3) 3_776 ?
N4 C11 1.334(5) . ?
N4 C10 1.346(4) . ?
N4 Cu2 2.128(3) 2_755 ?
N5 N6 1.168(4) . ?
N7 N7 1.178(6) 3_666 ?
C1 C2 1.380(5) . ?
C1 C5 1.384(5) . ?
C1 C6 1.508(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.375(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.379(5) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9300 . ?
C8 C9 1.515(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.379(5) . ?
C9 C13 1.392(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.379(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.388(5) . ?
C12 H12A 0.9300 . ?
C13 H13A 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
N2 Cu1 N3 171.93(13) . 3_776 ?
N2 Cu1 Cu1 86.77(9) . 3_776 ?
N3 Cu1 Cu1 86.32(9) 3_776 3_776 ?
N7 Cu2 N5 144.45(14) . . ?
N7 Cu2 N4 106.01(13) . 2_745 ?
N5 Cu2 N4 98.44(12) . 2_745 ?
N7 Cu2 N1 104.59(13) . . ?
N5 Cu2 N1 94.72(12) . . ?
N4 Cu2 N1 102.30(11) 2_745 . ?
N6 Cu3 N6 180.0 3_766 . ?
C2 N1 C3 116.6(3) . . ?
C2 N1 Cu2 119.8(2) . . ?
C3 N1 Cu2 122.5(2) . . ?
C7 N2 C6 116.9(3) . . ?
C7 N2 Cu1 120.8(2) . . ?
C6 N2 Cu1 122.3(2) . . ?
C7 N3 C8 117.8(3) . . ?
C7 N3 Cu1 121.0(2) . 3_776 ?
C8 N3 Cu1 121.0(2) . 3_776 ?
C11 N4 C10 117.4(3) . . ?
C11 N4 Cu2 119.9(2) . 2_755 ?
C10 N4 Cu2 122.7(2) . 2_755 ?
N6 N5 Cu2 156.9(3) . . ?
N5 N6 Cu3 171.9(3) . . ?
N7 N7 Cu2 172.9(4) 3_666 . ?
C2 C1 C5 117.0(3) . . ?
C2 C1 C6 119.8(3) . . ?
C5 C1 C6 123.2(3) . . ?
N1 C2 C1 124.9(3) . . ?
N1 C2 H2A 117.5 . . ?
C1 C2 H2A 117.5 . . ?
N1 C3 C4 122.5(3) . . ?
N1 C3 H3A 118.8 . . ?
C4 C3 H3A 118.8 . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 H4A 120.2 . . ?
C4 C5 C1 119.4(3) . . ?
C4 C5 H5A 120.3 . . ?
C1 C5 H5A 120.3 . . ?
N2 C6 C1 113.1(3) . . ?
N2 C6 H6A 109.0 . . ?
C1 C6 H6A 109.0 . . ?
N2 C6 H6B 109.0 . . ?
C1 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
N3 C7 N2 124.8(3) . . ?
N3 C7 H7A 117.6 . . ?
N2 C7 H7A 117.6 . . ?
N3 C8 C9 113.6(3) . . ?
N3 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
N3 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C13 117.8(3) . . ?
C10 C9 C8 120.9(3) . . ?
C13 C9 C8 121.3(3) . . ?
N4 C10 C9 123.8(3) . . ?
N4 C10 H10A 118.1 . . ?
C9 C10 H10A 118.1 . . ?
N4 C11 C12 123.1(3) . . ?
N4 C11 H11A 118.4 . . ?
C12 C11 H11A 118.4 . . ?
C11 C12 C13 118.9(4) . . ?
C11 C12 H12A 120.5 . . ?
C13 C12 H12A 120.5 . . ?
C12 C13 C9 118.9(4) . . ?
C12 C13 H13A 120.6 . . ?
C9 C13 H13A 120.6 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.120
####################################################################### 
# 
# 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 1056082'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 Cu3 N10 O'
_chemical_formula_weight         533.00

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   7.3329(3)
_cell_length_b                   18.6223(7)
_cell_length_c                   14.8934(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.642(2)
_cell_angle_gamma                90.00
_cell_volume                     1991.94(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4874
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.92

_exptl_crystal_description       COLUMN
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1068
_exptl_absorpt_coefficient_mu    3.201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5669
_exptl_absorpt_correction_T_max  0.7402
_exptl_absorpt_process_details   'sadabs v2008/1(bruker axs, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19095
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_sigmaI/netI    0.0745
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         28.28
_reflns_number_total             4943
_reflns_number_gt                2974
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0661P)²+1.9352P] 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         4943
_refine_ls_number_parameters     262
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1072
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1476
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.002
_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 0.44101(10) 0.06036(3) 0.47873(5) 0.04138(19) Uani 1 1 d . . .
Cu2 Cu 0.66439(11) 0.31225(3) 0.49626(5) 0.0449(2) Uani 1 1 d . . .
Cu3 Cu 0.62804(10) -0.00557(3) 0.20005(4) 0.0419(2) Uani 1 1 d . . .
N1 N 0.1240(6) 0.1377(2) 0.1143(3) 0.0403(10) Uani 1 1 d . . .
N2 N 0.1572(6) 0.0707(2) 0.4477(3) 0.0380(10) Uani 1 1 d . . .
N3 N 0.1488(7) 0.1400(2) 0.5747(3) 0.0507(12) Uani 1 1 d . . .
H3A H 0.2672 0.1463 0.5833 0.061 Uiso 1 1 calc R . .
N4 N 0.1094(6) 0.3973(2) 0.6809(3) 0.0394(10) Uani 1 1 d . . .
N5 N 0.5222(7) -0.0071(3) 0.3889(3) 0.0523(12) Uani 1 1 d U . .
N6 N 0.5536(7) -0.0165(2) 0.3165(3) 0.0429(11) Uani 1 1 d U . .
N7 N 0.5534(7) 0.1552(2) 0.4907(3) 0.0461(12) Uani 1 1 d . . .
N8 N 0.6002(8) 0.2143(3) 0.4920(3) 0.0559(13) Uani 1 1 d . . .
N9 N 0.7080(8) -0.0716(3) 0.1231(3) 0.0578(14) Uani 1 1 d U . .
N10 N 0.7611(7) -0.1153(2) 0.0783(3) 0.0489(12) Uani 1 1 d U . .
C1 C 0.1238(9) 0.0667(3) 0.1242(4) 0.0441(13) Uani 1 1 d . . .
H1A H 0.1378 0.0386 0.0744 0.053 Uiso 1 1 calc R . .
C2 C 0.1041(8) 0.0324(3) 0.2033(4) 0.0435(13) Uani 1 1 d . . .
H2A H 0.1051 -0.0175 0.2063 0.052 Uiso 1 1 calc R . .
C3 C 0.0828(7) 0.0729(3) 0.2783(3) 0.0353(11) Uani 1 1 d . . .
C4 C 0.0829(8) 0.1462(3) 0.2691(4) 0.0448(13) Uani 1 1 d . . .
H4A H 0.0688 0.1754 0.3180 0.054 Uiso 1 1 calc R . .
C5 C 0.1039(8) 0.1767(3) 0.1877(4) 0.0457(14) Uani 1 1 d . . .
H5A H 0.1043 0.2265 0.1832 0.055 Uiso 1 1 calc R . .
C6 C 0.0533(8) 0.0366(3) 0.3659(3) 0.0432(13) Uani 1 1 d . . .
H6A H -0.0782 0.0377 0.3675 0.052 Uiso 1 1 calc R . .
H6B H 0.0909 -0.0133 0.3652 0.052 Uiso 1 1 calc R . .
C7 C 0.0646(8) 0.1039(3) 0.4987(4) 0.0388(12) Uani 1 1 d . . .
H7A H -0.0647 0.1033 0.4832 0.047 Uiso 1 1 calc R . .
C8 C 0.0532(9) 0.1682(3) 0.6415(4) 0.0495(15) Uani 1 1 d . . .
H8A H 0.0971 0.1439 0.6994 0.059 Uiso 1 1 calc R . .
H8B H -0.0788 0.1584 0.6223 0.059 Uiso 1 1 calc R . .
C9 C 0.1188(9) 0.3668(3) 0.6006(4) 0.0468(14) Uani 1 1 d . . .
H9A H 0.1364 0.3964 0.5527 0.056 Uiso 1 1 calc R . .
C10 C 0.1039(9) 0.2946(3) 0.5852(4) 0.0484(14) Uani 1 1 d . . .
H10A H 0.1089 0.2762 0.5277 0.058 Uiso 1 1 calc R . .
C11 C 0.0812(8) 0.2487(3) 0.6558(4) 0.0422(13) Uani 1 1 d . . .
C12 C 0.0756(8) 0.2804(3) 0.7386(4) 0.0444(13) Uani 1 1 d . . .
H12A H 0.0628 0.2518 0.7882 0.053 Uiso 1 1 calc R . .
C13 C 0.0885(9) 0.3521(3) 0.7491(4) 0.0428(13) Uani 1 1 d . . .
H13A H 0.0826 0.3715 0.8060 0.051 Uiso 1 1 calc R . .
C14 C 0.2909(17) -0.1582(6) 0.1570(8) 0.118(4) Uani 0.50 1 d P A 1
H14A H 0.2220 -0.2010 0.1364 0.176 Uiso 0.50 1 calc PR A 1
H14B H 0.4162 -0.1631 0.1478 0.176 Uiso 0.50 1 calc PR A 1
H14C H 0.2328 -0.1178 0.1228 0.176 Uiso 0.50 1 calc PR A 1
O O 0.2932(18) -0.1482(6) 0.2463(8) 0.078(3) Uani 0.50 1 d P A 1
C14' C 0.2909(17) -0.1582(6) 0.1570(8) 0.118(4) Uani 0.50 1 d P B 2
H14D H 0.1903 -0.1851 0.1730 0.176 Uiso 0.50 1 calc PR B 2
H14E H 0.2847 -0.1616 0.0921 0.176 Uiso 0.50 1 calc PR B 2
H14F H 0.2811 -0.1088 0.1738 0.176 Uiso 0.50 1 calc PR B 2
O' O 0.437(6) -0.1822(18) 0.197(4) 0.64(7) Uani 0.50 1 d P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N7 1.942(4) . ?
Cu1 N5 2.011(5) . ?
Cu1 N2 2.048(5) . ?
Cu1 N5 2.174(5) 3_656 ?
Cu1 Cu1 2.4460(13) 3_656 ?
Cu2 N8 1.881(5) . ?
Cu2 N10 1.896(5) 2_655 ?
Cu2 N1 2.063(4) 4_666 ?
Cu3 N9 1.856(5) . ?
Cu3 N6 1.931(5) . ?
Cu3 N4 2.037(4) 4_665 ?
N1 C1 1.329(6) . ?
N1 C5 1.346(6) . ?
N1 Cu2 2.063(4) 4_565 ?
N2 C7 1.277(7) . ?
N2 C6 1.446(7) . ?
N3 C7 1.354(7) . ?
N3 C8 1.428(7) . ?
N3 H3A 0.8600 . ?
N4 C9 1.339(7) . ?
N4 C13 1.351(6) . ?
N4 Cu3 2.037(4) 4_566 ?
N5 N6 1.161(6) . ?
N5 Cu1 2.174(5) 3_656 ?
N7 N8 1.152(6) . ?
N9 N10 1.168(6) . ?
N10 Cu2 1.896(5) 2_645 ?
C1 C2 1.373(7) . ?
C1 H1A 0.9300 . ?
C2 C3 1.383(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.373(7) . ?
C3 C6 1.522(7) . ?
C4 C5 1.374(7) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9300 . ?
C8 C11 1.521(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.365(7) . ?
C9 H9A 0.9300 . ?
C10 C11 1.391(7) . ?
C10 H10A 0.9300 . ?
C11 C12 1.376(7) . ?
C12 C13 1.346(7) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 O 1.340(14) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
N7 Cu1 N5 116.9(2) . . ?
N7 Cu1 N2 109.21(19) . . ?
N5 Cu1 N2 109.38(19) . . ?
N7 Cu1 N5 111.01(19) . 3_656 ?
N5 Cu1 N5 108.59(16) . 3_656 ?
N2 Cu1 N5 100.49(18) . 3_656 ?
N7 Cu1 Cu1 133.68(15) . 3_656 ?
N5 Cu1 Cu1 57.40(14) . 3_656 ?
N2 Cu1 Cu1 115.77(12) . 3_656 ?
N5 Cu1 Cu1 51.19(13) 3_656 3_656 ?
N8 Cu2 N10 140.3(2) . 2_655 ?
N8 Cu2 N1 112.90(19) . 4_666 ?
N10 Cu2 N1 106.54(18) 2_655 4_666 ?
N9 Cu3 N6 131.8(2) . . ?
N9 Cu3 N4 126.2(2) . 4_665 ?
N6 Cu3 N4 101.92(17) . 4_665 ?
C1 N1 C5 116.3(5) . . ?
C1 N1 Cu2 123.2(4) . 4_565 ?
C5 N1 Cu2 120.4(3) . 4_565 ?
C7 N2 C6 117.5(5) . . ?
C7 N2 Cu1 123.3(4) . . ?
C6 N2 Cu1 119.2(4) . . ?
C7 N3 C8 124.1(5) . . ?
C7 N3 H3A 117.9 . . ?
C8 N3 H3A 117.9 . . ?
C9 N4 C13 116.2(5) . . ?
C9 N4 Cu3 122.0(3) . 4_566 ?
C13 N4 Cu3 121.8(3) . 4_566 ?
N6 N5 Cu1 148.5(4) . . ?
N6 N5 Cu1 139.7(4) . 3_656 ?
Cu1 N5 Cu1 71.41(16) . 3_656 ?
N5 N6 Cu3 164.6(4) . . ?
N8 N7 Cu1 171.9(5) . . ?
N7 N8 Cu2 176.8(5) . . ?
N10 N9 Cu3 176.7(5) . . ?
N9 N10 Cu2 177.3(5) . 2_645 ?
N1 C1 C2 124.1(5) . . ?
N1 C1 H1A 117.9 . . ?
C2 C1 H1A 117.9 . . ?
C1 C2 C3 119.2(5) . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 H2A 120.4 . . ?
C4 C3 C2 117.3(5) . . ?
C4 C3 C6 122.0(5) . . ?
C2 C3 C6 120.6(4) . . ?
C3 C4 C5 120.1(5) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
N1 C5 C4 123.0(5) . . ?
N1 C5 H5A 118.5 . . ?
C4 C5 H5A 118.5 . . ?
N2 C6 C3 112.7(4) . . ?
N2 C6 H6A 109.1 . . ?
C3 C6 H6A 109.1 . . ?
N2 C6 H6B 109.1 . . ?
C3 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
N2 C7 N3 122.1(5) . . ?
N2 C7 H7A 118.9 . . ?
N3 C7 H7A 118.9 . . ?
N3 C8 C11 112.9(5) . . ?
N3 C8 H8A 109.0 . . ?
C11 C8 H8A 109.0 . . ?
N3 C8 H8B 109.0 . . ?
C11 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
N4 C9 C10 123.4(5) . . ?
N4 C9 H9A 118.3 . . ?
C10 C9 H9A 118.3 . . ?
C9 C10 C11 119.8(5) . . ?
C9 C10 H10A 120.1 . . ?
C11 C10 H10A 120.1 . . ?
C12 C11 C10 116.4(5) . . ?
C12 C11 C8 121.3(5) . . ?
C10 C11 C8 122.3(5) . . ?
C13 C12 C11 121.0(5) . . ?
C13 C12 H12A 119.5 . . ?
C11 C12 H12A 119.5 . . ?
C12 C13 N4 123.2(5) . . ?
C12 C13 H13A 118.4 . . ?
N4 C13 H13A 118.4 . . ?
O C14 H14A 109.5 . . ?
O C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.625
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.109
