# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_xb0155
_database_code_depnum_ccdc_archive 'CCDC 1544574'
_audit_update_record             
;
2017-06-11 deposited with the CCDC.
2017-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H4 Cu N8 O4'
_chemical_formula_weight         279.69

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)/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                   8.914(7)
_cell_length_b                   10.497(9)
_cell_length_c                   9.251(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.776(13)
_cell_angle_gamma                90.00
_cell_volume                     828.7(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1882
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      26.88

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.33
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             556
_exptl_absorpt_coefficient_mu    2.656
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3963
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1455
_reflns_number_gt                1302
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0936P)²+4.2677P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1455
_refine_ls_number_parameters     136
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1583
_refine_ls_wR_factor_gt          0.1540
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
N5 N 0.5958(5) 0.8705(4) 0.9698(5) 0.0174(9) Uani 1 1 d . . .
N6 N 0.6495(6) 0.7679(4) 0.9220(5) 0.0233(10) Uani 1 1 d . . .
N7 N 0.5758(6) 0.7505(5) 0.7745(5) 0.0230(10) Uani 1 1 d . . .
N1 N 0.2741(4) 0.9926(3) 0.6131(3) 0.0213(10) Uani 1 1 d G . .
C2 C 0.3734(4) 0.8876(3) 0.6095(3) 0.0246(12) Uani 1 1 d G . .
N3 N 0.3439(4) 0.8486(3) 0.4569(3) 0.0246(11) Uani 1 1 d G . .
N2 N 0.2264(4) 0.9295(3) 0.3661(3) 0.0284(12) Uani 1 1 d G . .
H2 H 0.1881 0.9253 0.2696 0.034 Uiso 1 1 calc R . .
C1 C 0.1833(4) 1.0185(3) 0.4626(4) 0.0245(12) Uani 1 1 d G . .
H1 H 0.1086 1.0825 0.4326 0.029 Uiso 1 1 calc R . .
O4 O 0.1254(5) 1.1589(4) 0.7821(5) 0.0307(10) Uani 1 1 d D . .
Cu1 Cu 0.32602(8) 1.06779(6) 0.81876(7) 0.0206(3) Uani 1 1 d . . .
N4 N 0.4858(6) 0.9248(4) 0.8555(5) 0.0175(10) Uani 1 1 d . . .
O1 O 0.0102(6) 0.7814(5) 0.9878(5) 0.0388(11) Uani 1 1 d . . .
O2 O 0.1768(7) 0.9331(5) 1.0657(6) 0.0464(14) Uani 1 1 d . . .
N8 N 0.1005(6) 0.8647(5) 0.9629(5) 0.0244(11) Uani 1 1 d . . .
C3 C 0.4760(7) 0.8495(5) 0.7369(6) 0.0207(11) Uani 1 1 d . . .
H4A H 0.0895 1.1974 0.7083 0.007 Uiso 1 1 d . . .
H4B H 0.0839 1.1921 0.8447 0.058 Uiso 1 1 d D . .
O3 O 0.1104(6) 0.8796(5) 0.8325(5) 0.0422(12) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N5 0.022(2) 0.017(2) 0.012(2) -0.0014(17) 0.0023(18) 0.0028(18)
N6 0.025(2) 0.025(2) 0.018(2) -0.002(2) 0.0035(19) 0.008(2)
N7 0.025(2) 0.024(2) 0.017(2) -0.0055(19) 0.003(2) 0.005(2)
N1 0.026(3) 0.020(2) 0.017(2) -0.0007(19) 0.005(2) 0.0041(19)
C2 0.023(3) 0.019(3) 0.032(3) -0.003(2) 0.009(2) -0.003(2)
N3 0.026(3) 0.034(3) 0.009(2) -0.0039(19) -0.0017(19) 0.006(2)
N2 0.031(3) 0.035(3) 0.014(3) -0.0007(19) -0.001(2) 0.003(2)
C1 0.028(3) 0.027(3) 0.014(3) 0.000(2) -0.002(2) 0.003(2)
O4 0.028(2) 0.042(3) 0.020(2) 0.0055(18) 0.0039(17) 0.0135(19)
Cu1 0.0246(5) 0.0213(5) 0.0125(4) -0.0020(2) 0.0001(3) 0.0069(3)
N4 0.021(2) 0.018(2) 0.012(2) -0.0013(16) 0.0013(18) 0.0043(17)
O1 0.046(3) 0.040(3) 0.037(3) -0.007(2) 0.023(2) -0.017(2)
O2 0.060(4) 0.055(3) 0.022(3) -0.014(2) 0.008(2) -0.029(3)
N8 0.027(3) 0.027(3) 0.019(2) 0.001(2) 0.006(2) -0.001(2)
C3 0.025(3) 0.020(3) 0.019(3) -0.002(2) 0.010(2) -0.001(2)
O3 0.057(3) 0.048(3) 0.024(2) 0.003(2) 0.015(2) -0.007(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
N5 N6 1.306(6) . ?
N5 N4 1.343(6) . ?
N5 Cu1 1.986(4) 3_677 ?
N6 N7 1.346(7) . ?
N7 C3 1.347(7) . ?
N7 Cu1 2.371(5) 2_646 ?
N1 C2 1.4200 . ?
N1 C1 1.4200 . ?
N1 Cu1 1.987(3) . ?
C2 C3 1.327(6) . ?
C2 N3 1.4200 . ?
N3 N2 1.4200 . ?
N2 C1 1.4200 . ?
N2 H2 0.8600 . ?
C1 H1 0.9300 . ?
O4 Cu1 1.969(4) . ?
O4 H4A 0.7780 . ?
O4 H4B 0.8468 . ?
Cu1 N5 1.986(4) 3_677 ?
Cu1 N4 2.029(5) . ?
Cu1 N7 2.371(5) 2_656 ?
N4 C3 1.335(7) . ?
O1 N8 1.254(7) . ?
O2 N8 1.228(7) . ?
N8 O3 1.244(6) . ?

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
N6 N5 N4 109.9(4) . . ?
N6 N5 Cu1 122.9(3) . 3_677 ?
N4 N5 Cu1 127.2(3) . 3_677 ?
N5 N6 N7 109.6(4) . . ?
N6 N7 C3 104.4(4) . . ?
N6 N7 Cu1 110.8(3) . 2_646 ?
C3 N7 Cu1 144.7(4) . 2_646 ?
C2 N1 C1 108.0 . . ?
C2 N1 Cu1 110.86(19) . . ?
C1 N1 Cu1 140.50(19) . . ?
C3 C2 N3 132.7(3) . . ?
C3 C2 N1 119.2(3) . . ?
N3 C2 N1 108.0 . . ?
C2 N3 N2 108.0 . . ?
C1 N2 N3 108.0 . . ?
C1 N2 H2 126.0 . . ?
N3 N2 H2 126.0 . . ?
N2 C1 N1 108.0 . . ?
N2 C1 H1 126.0 . . ?
N1 C1 H1 126.0 . . ?
Cu1 O4 H4A 121.7 . . ?
Cu1 O4 H4B 129.5 . . ?
H4A O4 H4B 103.7 . . ?
O4 Cu1 N5 93.11(18) . 3_677 ?
O4 Cu1 N1 94.55(16) . . ?
N5 Cu1 N1 172.33(16) 3_677 . ?
O4 Cu1 N4 161.24(19) . . ?
N5 Cu1 N4 92.66(18) 3_677 . ?
N1 Cu1 N4 79.91(16) . . ?
O4 Cu1 N7 87.51(19) . 2_656 ?
N5 Cu1 N7 91.88(18) 3_677 2_656 ?
N1 Cu1 N7 88.93(17) . 2_656 ?
N4 Cu1 N7 110.12(19) . 2_656 ?
C3 N4 N5 104.8(4) . . ?
C3 N4 Cu1 115.1(4) . . ?
N5 N4 Cu1 139.8(3) . . ?
O2 N8 O3 120.0(5) . . ?
O2 N8 O1 120.4(5) . . ?
O3 N8 O1 119.6(5) . . ?
C2 C3 N4 114.6(5) . . ?
C2 C3 N7 134.1(5) . . ?
N4 C3 N7 111.3(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.86 1.86 2.685(6) 159.8 1_554
O4 H4A O1 0.78 1.98 2.758(6) 175.0 2_556
O4 H4A O3 0.78 2.57 3.102(7) 127.4 2_556
O4 H4A N8 0.78 2.63 3.350(6) 154.9 2_556
O4 H4B O1 0.85 1.98 2.805(6) 163.5 3_577

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         2.010
_refine_diff_density_min         -2.110
_refine_diff_density_rms         0.161
####################################################################### 
# 
# 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_xb0413
_database_code_depnum_ccdc_archive 'CCDC 1544575'
_audit_update_record             
;
2017-08-09 deposited with the CCDC.
2017-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 Cu N14 O4'
_chemical_formula_weight         427.83

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)/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                   6.276(3)
_cell_length_b                   14.093(6)
_cell_length_c                   8.649(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.608(5)
_cell_angle_gamma                90.00
_cell_volume                     754.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    454
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      21.10

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.884
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             430
_exptl_absorpt_coefficient_mu    1.506
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3624
_diffrn_reflns_av_R_equivalents  0.0763
_diffrn_reflns_av_sigmaI/netI    0.0965
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         24.98
_reflns_number_total             1331
_reflns_number_gt                811
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0431P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1331
_refine_ls_number_parameters     124
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.0919
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.962
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N5 N 1.2982(7) 0.6427(3) 0.3613(5) 0.0339(12) Uani 1 1 d . . .
N6 N 1.3227(7) 0.7339(3) 0.3721(5) 0.0346(12) Uani 1 1 d . . .
N7 N 1.1775(7) 0.7705(3) 0.4541(5) 0.0337(12) Uani 1 1 d DU . .
H3 H 1.1614 0.8291 0.4770 0.040 Uiso 1 1 calc RD . .
C1 C 1.0666(8) 0.6982(4) 0.4915(6) 0.0268(14) Uani 1 1 d . . .
N4 N 1.1362(7) 0.6177(3) 0.4367(5) 0.0271(12) Uani 1 1 d . . .
Cu1 Cu 1.0000 0.5000 0.5000 0.0288(3) Uani 1 2 d S . .
N3 N 0.8208(7) 0.5948(3) 0.5888(5) 0.0278(11) Uani 1 1 d . . .
N2 N 0.7789(7) 0.7474(3) 0.6470(6) 0.0343(12) Uani 1 1 d . . .
N1 N 0.6361(7) 0.6906(3) 0.7050(5) 0.0326(12) Uani 1 1 d . . .
H2 H 0.5404 0.7107 0.7577 0.039 Uiso 1 1 calc R . .
C2 C 0.8847(8) 0.6858(3) 0.5761(6) 0.0257(13) Uani 1 1 d . . .
C3 C 0.6626(9) 0.6014(4) 0.6706(6) 0.0311(14) Uani 1 1 d . . .
H1 H 0.5824 0.5508 0.6994 0.037 Uiso 1 1 calc R . .
O1 O 1.2331(6) 0.5249(3) 0.7618(5) 0.0479(12) Uani 1 1 d . . .
O2 O 1.2377(7) 0.5397(3) 1.0192(5) 0.0557(13) Uani 1 1 d U . .
C4 C 1.2352(9) 0.4901(4) 0.8870(9) 0.0495(17) Uani 1 1 d . . .
H4 H 1.2471 0.4147 0.9192 0.089 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N5 0.041(3) 0.030(3) 0.036(3) 0.000(2) 0.024(3) -0.009(2)
N6 0.040(3) 0.026(3) 0.043(3) 0.000(2) 0.022(3) -0.007(2)
N7 0.043(3) 0.016(2) 0.046(3) -0.002(2) 0.020(2) -0.006(2)
C1 0.034(3) 0.019(3) 0.031(3) -0.002(2) 0.016(3) -0.001(2)
N4 0.035(3) 0.022(2) 0.030(3) 0.000(2) 0.021(2) 0.001(2)
Cu1 0.0349(5) 0.0147(4) 0.0433(6) -0.0007(5) 0.0256(4) -0.0005(5)
N3 0.032(3) 0.017(2) 0.039(3) 0.003(2) 0.020(2) -0.007(2)
N2 0.040(3) 0.022(2) 0.046(3) 0.002(2) 0.024(3) 0.000(2)
N1 0.034(3) 0.027(2) 0.042(3) -0.003(2) 0.024(3) 0.008(2)
C2 0.034(3) 0.020(3) 0.027(3) 0.002(2) 0.015(3) 0.001(2)
C3 0.034(3) 0.024(3) 0.040(4) 0.001(3) 0.020(3) 0.001(3)
O1 0.053(3) 0.053(3) 0.042(3) 0.001(2) 0.017(2) -0.007(2)
O2 0.087(3) 0.041(2) 0.042(3) -0.001(2) 0.018(2) 0.000(2)
C4 0.053(4) 0.036(4) 0.062(5) -0.001(4) 0.016(4) 0.000(3)

_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
N5 N6 1.297(5) . ?
N5 N4 1.343(5) . ?
N6 N7 1.347(6) . ?
N7 C1 1.304(6) . ?
N7 H3 0.8600 . ?
C1 N4 1.332(6) . ?
C1 C2 1.466(6) . ?
N4 Cu1 1.984(4) . ?
Cu1 N3 1.982(4) . ?
Cu1 N3 1.982(4) 3_766 ?
Cu1 N4 1.984(4) 3_766 ?
Cu1 O1 2.507(4) . ?
N3 C3 1.315(6) . ?
N3 C2 1.354(6) . ?
N2 C2 1.306(6) . ?
N2 N1 1.359(5) . ?
N1 C3 1.309(6) . ?
N1 H2 0.8600 . ?
C3 H1 0.9300 . ?
O1 C4 1.188(7) . ?
O2 C4 1.337(7) . ?
C4 H4 1.0978 . ?

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
N6 N5 N4 108.4(4) . . ?
N5 N6 N7 109.6(4) . . ?
C1 N7 N6 105.6(4) . . ?
C1 N7 H3 127.2 . . ?
N6 N7 H3 127.2 . . ?
N7 C1 N4 110.9(4) . . ?
N7 C1 C2 135.2(5) . . ?
N4 C1 C2 113.9(4) . . ?
C1 N4 N5 105.6(4) . . ?
C1 N4 Cu1 115.6(3) . . ?
N5 N4 Cu1 138.5(3) . . ?
N3 Cu1 N3 180.0(2) . 3_766 ?
N3 Cu1 N4 80.92(16) . . ?
N3 Cu1 N4 99.08(16) 3_766 . ?
N3 Cu1 N4 99.08(16) . 3_766 ?
N3 Cu1 N4 80.92(16) 3_766 3_766 ?
N4 Cu1 N4 180.000(1) . 3_766 ?
N3 Cu1 O1 80.73(17) . . ?
N3 Cu1 O1 99.27(17) 3_766 . ?
N4 Cu1 O1 85.36(16) . . ?
N4 Cu1 O1 94.64(16) 3_766 . ?
C3 N3 C2 103.7(4) . . ?
C3 N3 Cu1 141.7(3) . . ?
C2 N3 Cu1 114.3(3) . . ?
C2 N2 N1 101.5(4) . . ?
C3 N1 N2 111.5(4) . . ?
C3 N1 H2 124.3 . . ?
N2 N1 H2 124.3 . . ?
N2 C2 N3 114.3(4) . . ?
N2 C2 C1 130.9(4) . . ?
N3 C2 C1 114.8(4) . . ?
N1 C3 N3 109.0(4) . . ?
N1 C3 H1 125.5 . . ?
N3 C3 H1 125.5 . . ?
C4 O1 Cu1 133.0(4) . . ?
O1 C4 O2 124.1(6) . . ?
O1 C4 H4 128.4 . . ?
O2 C4 H4 107.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H2 N6 0.86 1.98 2.835(6) 175.9 4_476
N7 H3 O2 0.86 1.93 2.748(6) 158.4 4_575

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.094
