# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_xb8008_0m
_database_code_depnum_ccdc_archive 'CCDC 1860912'
loop_
_audit_author_name
_audit_author_address
'Xiangyu Liu'
;Ningxia University
China
;
_audit_update_record             
;
2019-02-26 deposited with the CCDC.	2019-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H4 Cu N6 O2'
_chemical_formula_weight         267.70

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

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

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

_cell_length_a                   6.905(4)
_cell_length_b                   7.141(4)
_cell_length_c                   9.596(5)
_cell_angle_alpha                100.558(7)
_cell_angle_beta                 97.836(9)
_cell_angle_gamma                101.571(9)
_cell_volume                     448.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    763
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      24.93

_exptl_crystal_description       bulk
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.983
_exptl_crystal_F_000             266
_exptl_transmission_factor_min   0.6376
_exptl_transmission_factor_max   0.7455
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.429
_shelx_estimated_absorpt_T_min   0.459
_shelx_estimated_absorpt_T_max   0.642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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            2295
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.195
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             1611
_reflns_number_gt                1167
_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-2018/1 (Sheldrick, 2018)'
_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)+(0.1465P)²] 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         1611
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.2210
_refine_ls_wR_factor_gt          0.1955
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_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 0.500000 1.000000 0.500000 0.0236(4) Uani 1 2 d S . P . .
Cu2 Cu 0.500000 0.500000 0.500000 0.0262(5) Uani 1 2 d S . P . .
O1 O 0.3609(8) 1.0380(7) 0.3180(5) 0.0305(13) Uani 1 1 d . . . . .
O2 O 0.4569(10) 1.3525(7) 0.3028(5) 0.0371(14) Uani 1 1 d . . . . .
N1 N 0.3993(10) 0.7134(9) 0.4257(6) 0.0298(15) Uani 1 1 d . . . . .
N2 N 0.2611(11) 0.6527(9) 0.3218(7) 0.0313(15) Uani 1 1 d . . . . .
N3 N 0.1296(12) 0.5955(10) 0.2259(8) 0.047(2) Uani 1 1 d . . . . .
N4 N 0.1421(12) 0.9763(9) -0.3627(7) 0.0393(18) Uani 1 1 d . . . . .
N5 N 0.0230(11) 0.8149(10) -0.4195(7) 0.0369(17) Uani 1 1 d . . . . .
N6 N -0.0849(12) 0.6767(11) -0.4856(8) 0.045(2) Uani 1 1 d . . . . .
C3 C 0.3144(11) 1.1194(10) 0.0899(7) 0.0242(15) Uani 1 1 d . . . . .
C6 C 0.3850(11) 1.1740(10) 0.2483(7) 0.0239(16) Uani 1 1 d . . . . .
C8 C 0.1999(11) 1.0178(11) -0.2092(7) 0.0268(16) Uani 1 1 d . . . . .
C10 C 0.2827(12) 1.2118(11) -0.1421(8) 0.0321(18) Uani 1 1 d . . . . .
H10 H 0.302373 1.307228 -0.196299 0.039 Uiso 1 1 calc R U . . .
C11 C 0.1765(12) 0.8715(11) -0.1305(8) 0.0314(18) Uani 1 1 d . . . . .
H11 H 0.123634 0.741296 -0.176998 0.038 Uiso 1 1 calc R U . . .
C12 C 0.2333(12) 0.9233(11) 0.0187(8) 0.0324(18) Uani 1 1 d . . . . .
H12 H 0.217323 0.826615 0.072065 0.039 Uiso 1 1 calc R U . . .
C13 C 0.3361(12) 1.2625(11) 0.0077(8) 0.0327(19) Uani 1 1 d . . . . .
H13 H 0.386877 1.393256 0.053585 0.039 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 1.966(5) 2_676 ?
Cu1 O1 1.966(5) . ?
Cu1 N1 1.985(6) 2_676 ?
Cu1 N1 1.985(6) . ?
Cu2 O2 1.942(5) 2_676 ?
Cu2 O2 1.942(5) 1_545 ?
Cu2 N1 2.001(6) . ?
Cu2 N1 2.001(6) 2_666 ?
O1 C6 1.274(9) . ?
O2 C6 1.256(9) . ?
N1 N2 1.228(9) . ?
N2 N3 1.150(9) . ?
N4 N5 1.253(9) . ?
N4 C8 1.432(9) . ?
N5 N6 1.130(9) . ?
C3 C13 1.398(10) . ?
C3 C12 1.404(10) . ?
C3 C6 1.485(9) . ?
C8 C10 1.384(10) . ?
C8 C11 1.394(10) . ?
C10 C13 1.395(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.391(10) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13 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 O1 180.0(3) 2_676 . ?
O1 Cu1 N1 88.2(2) 2_676 2_676 ?
O1 Cu1 N1 91.8(2) . 2_676 ?
O1 Cu1 N1 91.8(2) 2_676 . ?
O1 Cu1 N1 88.2(2) . . ?
N1 Cu1 N1 180.0 2_676 . ?
O2 Cu2 O2 180.0 2_676 1_545 ?
O2 Cu2 N1 91.2(2) 2_676 . ?
O2 Cu2 N1 88.8(2) 1_545 . ?
O2 Cu2 N1 88.8(2) 2_676 2_666 ?
O2 Cu2 N1 91.2(2) 1_545 2_666 ?
N1 Cu2 N1 180.0 . 2_666 ?
C6 O1 Cu1 134.2(5) . . ?
C6 O2 Cu2 131.2(5) . 1_565 ?
N2 N1 Cu1 119.3(5) . . ?
N2 N1 Cu2 113.5(5) . . ?
Cu1 N1 Cu2 127.2(3) . . ?
N3 N2 N1 179.0(9) . . ?
N5 N4 C8 116.3(7) . . ?
N6 N5 N4 171.8(7) . . ?
C13 C3 C12 118.6(7) . . ?
C13 C3 C6 120.2(6) . . ?
C12 C3 C6 121.1(6) . . ?
O2 C6 O1 125.5(7) . . ?
O2 C6 C3 116.8(6) . . ?
O1 C6 C3 117.7(6) . . ?
C10 C8 C11 121.3(6) . . ?
C10 C8 N4 116.5(7) . . ?
C11 C8 N4 122.2(6) . . ?
C8 C10 C13 119.2(7) . . ?
C8 C10 H10 120.4 . . ?
C13 C10 H10 120.4 . . ?
C12 C11 C8 119.0(7) . . ?
C12 C11 H11 120.5 . . ?
C8 C11 H11 120.5 . . ?
C11 C12 C3 120.9(7) . . ?
C11 C12 H12 119.5 . . ?
C3 C12 H12 119.5 . . ?
C10 C13 C3 120.9(7) . . ?
C10 C13 H13 119.5 . . ?
C3 C13 H13 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu2 O2 C6 O1 -15.8(13) 1_565 . . . ?
Cu2 O2 C6 C3 161.4(5) 1_565 . . . ?
Cu1 O1 C6 O2 -29.3(13) . . . . ?
Cu1 O1 C6 C3 153.5(5) . . . . ?
C13 C3 C6 O2 2.3(11) . . . . ?
C12 C3 C6 O2 179.4(7) . . . . ?
C13 C3 C6 O1 179.8(7) . . . . ?
C12 C3 C6 O1 -3.1(11) . . . . ?
N5 N4 C8 C10 -162.3(8) . . . . ?
N5 N4 C8 C11 18.2(12) . . . . ?
C11 C8 C10 C13 -2.6(12) . . . . ?
N4 C8 C10 C13 178.0(8) . . . . ?
C10 C8 C11 C12 1.5(13) . . . . ?
N4 C8 C11 C12 -179.0(8) . . . . ?
C8 C11 C12 C3 -0.4(13) . . . . ?
C13 C3 C12 C11 0.3(12) . . . . ?
C6 C3 C12 C11 -176.8(7) . . . . ?
C8 C10 C13 C3 2.5(13) . . . . ?
C12 C3 C13 C10 -1.4(12) . . . . ?
C6 C3 C13 C10 175.8(7) . . . . ?

_refine_diff_density_max         1.350
_refine_diff_density_min         -1.240
_refine_diff_density_rms         0.273

####################################################################### 
# 
# 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_xb7308_0m
_database_code_depnum_ccdc_archive 'CCDC 1860913'
loop_
_audit_author_name
_audit_author_address
'Xiangyu Liu'
;Ningxia University
China
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-06-24 downloaded from the CCDC.
;
_audit_creation_date             2019-06-05
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H8 Cu N6 O3'
_chemical_formula_sum            'C8 H8 Cu N6 O3'
_chemical_formula_weight         299.74
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.409(8)
_cell_length_b                   7.557(10)
_cell_length_c                   13.189(17)
_cell_angle_alpha                106.52(2)
_cell_angle_beta                 95.63(2)
_cell_angle_gamma                90.35(2)
_cell_volume                     609.1(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    781
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.5174
_cell_measurement_theta_min      2.8134
_shelx_estimated_absorpt_T_max   0.786
_shelx_estimated_absorpt_T_min   0.623
_exptl_absorpt_coefficient_mu    1.803
_exptl_absorpt_correction_T_max  0.852
_exptl_absorpt_correction_T_min  0.552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       flake
_exptl_crystal_F_000             302
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.1000
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2890
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         1.619
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    .
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1236
_reflns_number_total             2082
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         2.262
_refine_diff_density_min         -1.078
_refine_diff_density_rms         0.198
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2082
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1300
_refine_ls_R_factor_gt           0.0915
_refine_ls_restrained_S_all      1.160
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1161P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2208
_refine_ls_wR_factor_ref         0.2374
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N6) \\sim Ueq, Uanis(N3) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 O3(H3)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C6(H6), C7(H7)
3.c Fitted hexagon refined as free rotating group:
 C2(C3,C4,C5,C6,C7)
3.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.000000 0.500000 0.500000 0.0323(5) Uani 1 2 d S T P . .
Cu2 Cu 0.500000 0.500000 0.500000 0.0324(5) Uani 1 2 d S T P . .
O1 O 0.0938(9) 0.7072(8) 0.6249(5) 0.0386(17) Uani 1 1 d . . . . .
O2 O 0.4535(9) 0.7040(9) 0.6214(5) 0.0402(17) Uani 1 1 d . . . . .
O3 O 0.2302(11) 0.6401(10) 0.3999(6) 0.0495(18) Uani 1 1 d . . . . .
H3 H 0.236853 0.774920 0.428700 0.059 Uiso 1 1 calc R . . . .
N1 N 0.2541(11) 0.3589(10) 0.5257(7) 0.041(2) Uani 1 1 d . . . . .
N2 N 0.2471(13) 0.1934(12) 0.4972(8) 0.055(3) Uani 1 1 d . . . . .
N3 N 0.2428(16) 0.0340(13) 0.4742(11) 0.093(4) Uani 1 1 d . U . . .
N4 N 0.364(2) 1.3372(18) 1.0536(9) 0.097(4) Uani 1 1 d . . . . .
N5 N 0.561(3) 1.394(2) 1.0979(12) 0.108(5) Uani 1 1 d . . . . .
N6 N 0.721(3) 1.442(2) 1.1411(14) 0.141(7) Uani 1 1 d . U . . .
C1 C 0.2804(16) 0.7672(13) 0.6607(8) 0.045(3) Uani 1 1 d . . . . .
C2 C 0.3050(10) 0.9213(9) 0.7627(5) 0.042(2) Uani 1 1 d . . . . .
C3 C 0.1309(8) 0.9852(10) 0.8156(6) 0.064(4) Uani 1 1 d G . . . .
H3A H -0.002050 0.935282 0.786654 0.077 Uiso 1 1 calc R . . . .
C4 C 0.1557(10) 1.1237(11) 0.9117(6) 0.082(5) Uani 1 1 d G . . . .
H4 H 0.039202 1.166411 0.947136 0.099 Uiso 1 1 calc R . . . .
C5 C 0.3544(12) 1.1983(10) 0.9550(5) 0.057(3) Uani 1 1 d G . . . .
C6 C 0.5285(9) 1.1344(10) 0.9021(6) 0.075(4) Uani 1 1 d G . . . .
H6 H 0.661463 1.184356 0.930978 0.090 Uiso 1 1 calc R . . . .
C7 C 0.5038(8) 0.9960(10) 0.8059(6) 0.059(3) Uani 1 1 d G . . . .
H7 H 0.620215 0.953227 0.770495 0.071 Uiso 1 1 calc R . . . .
C8 C 0.196(2) 0.588(2) 0.2866(10) 0.096(5) Uani 1 1 d . . . . .
H8A H 0.211932 0.457250 0.259067 0.143 Uiso 1 1 calc GR . . . .
H8B H 0.297249 0.652441 0.259656 0.143 Uiso 1 1 calc GR . . . .
H8C H 0.057433 0.619077 0.264972 0.143 Uiso 1 1 calc GR . . . .


_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 1.963(6) . ?
Cu1 O1 1.963(6) 2_566 ?
Cu1 O3 2.490(7) . ?
Cu1 N1 2.006(8) 2_566 ?
Cu1 N1 2.006(8) . ?
Cu2 O2 1.930(6) . ?
Cu2 O2 1.930(6) 2_666 ?
Cu2 O3 2.495(8) . ?
Cu2 N1 2.007(7) 2_666 ?
Cu2 N1 2.007(7) . ?
O1 C1 1.273(11) . ?
O2 C1 1.306(11) . ?
O3 H3 0.9800 . ?
O3 C8 1.426(13) . ?
N1 N2 1.198(11) . ?
N2 N3 1.155(11) . ?
N4 N5 1.354(19) . ?
N4 C5 1.415(12) . ?
N5 N6 1.126(18) . ?
C1 C2 1.502(11) . ?
C2 C3 1.3900 . ?
C2 C7 1.3900 . ?
C3 H3A 0.9300 . ?
C3 C4 1.3900 . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C6 H6 0.9300 . ?
C6 C7 1.3900 . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
O1 Cu1 O1 180.0(3) . 2_566 ?
O1 Cu1 O3 86.7(3) . . ?
O1 Cu1 O3 93.3(3) 2_566 . ?
O1 Cu1 N1 91.1(3) . . ?
O1 Cu1 N1 88.9(3) . 2_566 ?
O1 Cu1 N1 91.1(3) 2_566 2_566 ?
O1 Cu1 N1 88.9(3) 2_566 . ?
N1 Cu1 O3 84.4(3) . . ?
N1 Cu1 O3 95.6(3) 2_566 . ?
N1 Cu1 N1 180.0 . 2_566 ?
O2 Cu2 O2 180.0 2_666 . ?
O2 Cu2 O3 94.5(3) 2_666 . ?
O2 Cu2 O3 85.5(3) . . ?
O2 Cu2 N1 89.6(3) . 2_666 ?
O2 Cu2 N1 89.6(3) 2_666 . ?
O2 Cu2 N1 90.4(3) . . ?
O2 Cu2 N1 90.4(3) 2_666 2_666 ?
N1 Cu2 O3 95.7(3) 2_666 . ?
N1 Cu2 O3 84.3(3) . . ?
N1 Cu2 N1 180.0 . 2_666 ?
C1 O1 Cu1 128.3(6) . . ?
C1 O2 Cu2 130.9(6) . . ?
Cu1 O3 Cu2 80.0(2) . . ?
Cu1 O3 H3 110.4 . . ?
Cu2 O3 H3 110.4 . . ?
C8 O3 Cu1 119.2(7) . . ?
C8 O3 Cu2 123.2(8) . . ?
C8 O3 H3 110.4 . . ?
Cu1 N1 Cu2 106.0(4) . . ?
N2 N1 Cu1 120.3(7) . . ?
N2 N1 Cu2 120.3(6) . . ?
N3 N2 N1 177.1(14) . . ?
N5 N4 C5 114.0(12) . . ?
N6 N5 N4 175.5(19) . . ?
O1 C1 O2 127.3(9) . . ?
O1 C1 C2 116.3(8) . . ?
O2 C1 C2 116.3(8) . . ?
C3 C2 C1 120.3(6) . . ?
C3 C2 C7 120.0 . . ?
C7 C2 C1 119.7(6) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 N4 115.8(7) . . ?
C6 C5 N4 124.2(7) . . ?
C6 C5 C4 120.0 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C7 C6 H6 120.0 . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 120.0 . . ?
C6 C7 H7 120.0 . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
_geom_hbond_publ_flag
O3 H3 N3 0.98 1.88 2.855(12) 175.9 1_565 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 O2 0.4(16) . . . . ?
Cu1 O1 C1 C2 -176.1(6) . . . . ?
Cu2 O2 C1 O1 -1.3(16) . . . . ?
Cu2 O2 C1 C2 175.2(6) . . . . ?
O1 C1 C2 C3 3.1(11) . . . . ?
O1 C1 C2 C7 -179.1(7) . . . . ?
O2 C1 C2 C3 -173.8(7) . . . . ?
O2 C1 C2 C7 4.0(11) . . . . ?
N4 C5 C6 C7 179.3(10) . . . . ?
N5 N4 C5 C4 174.1(10) . . . . ?
N5 N4 C5 C6 -5.3(16) . . . . ?
C1 C2 C3 C4 177.9(8) . . . . ?
C1 C2 C7 C6 -177.9(8) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C2 C7 C6 0.0 . . . . ?
C3 C4 C5 N4 -179.4(10) . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C5 C6 C7 C2 0.0 . . . . ?
C7 C2 C3 C4 0.0 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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 1860914'
loop_
_audit_author_name
_audit_author_address
'Xiangyu Liu'
;Ningxia University
China
;
_audit_update_record             
;
2019-02-26 deposited with the CCDC.	2019-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 Cu N6 O3'
_chemical_formula_weight         313.77

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.622(3)
_cell_length_b                   6.304(2)
_cell_length_c                   27.572(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.690(6)
_cell_angle_gamma                90
_cell_volume                     1324.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1112
_cell_measurement_theta_min      3.32
_cell_measurement_theta_max      22.92

_exptl_crystal_description       STRIP
_exptl_crystal_colour            GREEN
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_F_000             636
_exptl_transmission_factor_min   0.6009
_exptl_transmission_factor_max   0.7458
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.663
_shelx_estimated_absorpt_T_min   0.578
_shelx_estimated_absorpt_T_max   0.754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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            6338
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.478
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             2383
_reflns_number_gt                1555
_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-2018/1 (Sheldrick, 2018)'
_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)+(0.1154P)²] 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         2383
_refine_ls_number_parameters     173
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1973
_refine_ls_wR_factor_gt          0.1451
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.091
_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 0.25498(8) 0.68734(12) 0.24867(2) 0.0250(3) Uani 1 1 d . . . . .
O1 O 0.4019(6) 0.7597(7) 0.30594(15) 0.0349(11) Uani 1 1 d . . . . .
C1 C 0.4292(7) 0.9366(10) 0.3257(2) 0.0275(13) Uani 1 1 d . . . . .
C2 C 0.5269(7) 0.9336(10) 0.3731(2) 0.0274(13) Uani 1 1 d . . . . .
C5 C 0.7048(9) 0.9290(13) 0.4619(2) 0.0432(18) Uani 1 1 d . . . . .
C3 C 0.6135(9) 0.7514(11) 0.3892(2) 0.0410(17) Uani 1 1 d . . . . .
H3 H 0.610164 0.629168 0.370292 0.049 Uiso 1 1 calc R U . . .
C6 C 0.6162(8) 1.1116(12) 0.4468(2) 0.0409(17) Uani 1 1 d . . . . .
H6 H 0.614287 1.230295 0.466810 0.049 Uiso 1 1 calc R U . . .
C7 C 0.5339(9) 1.1155(11) 0.4033(2) 0.0370(16) Uani 1 1 d . . . . .
H7 H 0.480035 1.240125 0.392656 0.044 Uiso 1 1 calc R U . . .
C4 C 0.7047(10) 0.7525(14) 0.4333(3) 0.055(2) Uani 1 1 d . . . . .
H4 H 0.766189 0.632319 0.443507 0.066 Uiso 1 1 calc R U . . .
N5 N 0.8088(9) 1.0809(16) 0.5319(3) 0.071(2) Uani 1 1 d . . . . .
N4 N 0.8048(9) 0.9141(14) 0.5072(2) 0.066(2) Uani 1 1 d . . . . .
N6 N 0.8256(12) 1.2168(18) 0.5570(3) 0.105(3) Uani 1 1 d . . . . .
N1 N 0.4030(6) 0.4312(7) 0.23831(19) 0.0290(12) Uani 1 1 d . . . . .
N2 N 0.5574(7) 0.4297(8) 0.2532(2) 0.0481(16) Uani 1 1 d . . . . .
N3 N 0.6993(9) 0.4267(12) 0.2642(4) 0.082(3) Uani 1 1 d . U . . .
O3 O 0.4330(5) 0.9359(7) 0.20484(16) 0.0360(11) Uani 1 1 d . . . . .
H7A H 0.509492 1.022099 0.222853 0.043 Uiso 1 1 calc R U . . .
C8 C 0.4291(10) 0.9600(12) 0.1531(3) 0.0503(19) Uani 1 1 d . . . . .
H8A H 0.494010 1.086668 0.144847 0.060 Uiso 1 1 calc R U . . .
H8B H 0.308494 0.979564 0.141789 0.060 Uiso 1 1 calc R U . . .
C9 C 0.5030(12) 0.7801(17) 0.1281(3) 0.079(3) Uani 1 1 d . . . . .
H9A H 0.618503 0.751129 0.141227 0.119 Uiso 1 1 calc R U . . .
H9B H 0.509816 0.812000 0.094113 0.119 Uiso 1 1 calc R U . . .
H9C H 0.429596 0.658109 0.132233 0.119 Uiso 1 1 calc R U . . .
O2 O 0.1166(6) 0.6163(7) 0.19012(16) 0.0345(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.954(4) . ?
Cu1 O1 1.962(4) . ?
Cu1 N1 1.992(5) 2 ?
Cu1 N1 1.995(5) . ?
Cu1 O3 2.419(4) . ?
O1 C1 1.257(7) . ?
C1 O2 1.259(7) 2 ?
C1 C2 1.485(8) . ?
C2 C3 1.391(9) . ?
C2 C7 1.417(8) . ?
C5 C4 1.364(10) . ?
C5 C6 1.393(10) . ?
C5 N4 1.446(8) . ?
C3 C4 1.383(9) . ?
C3 H3 0.9300 . ?
C6 C7 1.337(9) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C4 H4 0.9300 . ?
N5 N6 1.106(11) . ?
N5 N4 1.253(11) . ?
N1 N2 1.234(7) . ?
N2 N3 1.115(7) . ?
O3 C8 1.434(8) . ?
O3 H7A 0.9300 . ?
C8 C9 1.450(11) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
O2 Cu1 O1 177.78(19) . . ?
O2 Cu1 N1 90.65(19) . 2 ?
O1 Cu1 N1 90.54(19) . 2 ?
O2 Cu1 N1 89.42(19) . . ?
O1 Cu1 N1 89.51(19) . . ?
N1 Cu1 N1 176.20(16) 2 . ?
O2 Cu1 O3 91.87(18) . . ?
O1 Cu1 O3 86.34(17) . . ?
N1 Cu1 O3 86.63(18) 2 . ?
N1 Cu1 O3 97.16(17) . . ?
C1 O1 Cu1 129.7(4) . . ?
O1 C1 O2 127.4(5) . 2 ?
O1 C1 C2 116.3(5) . . ?
O2 C1 C2 116.3(6) 2 . ?
C3 C2 C7 118.2(5) . . ?
C3 C2 C1 120.8(6) . . ?
C7 C2 C1 121.0(6) . . ?
C4 C5 C6 120.6(6) . . ?
C4 C5 N4 116.0(7) . . ?
C6 C5 N4 123.5(7) . . ?
C4 C3 C2 119.8(7) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C7 C6 C5 119.6(7) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C2 121.4(6) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
C5 C4 C3 120.3(7) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
N6 N5 N4 172.2(10) . . ?
N5 N4 C5 114.8(8) . . ?
N2 N1 Cu1 120.7(4) . 2_545 ?
N2 N1 Cu1 119.7(4) . . ?
Cu1 N1 Cu1 104.5(2) 2_545 . ?
N3 N2 N1 176.4(9) . . ?
C8 O3 Cu1 124.8(4) . . ?
C8 O3 H7A 117.6 . . ?
Cu1 O3 H7A 117.6 . . ?
O3 C8 C9 113.2(7) . . ?
O3 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
O3 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 O2 Cu1 129.0(4) 2_545 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 O2 -9.0(9) . . . 2 ?
Cu1 O1 C1 C2 171.2(4) . . . . ?
O1 C1 C2 C3 12.9(9) . . . . ?
O2 C1 C2 C3 -167.0(6) 2 . . . ?
O1 C1 C2 C7 -166.8(6) . . . . ?
O2 C1 C2 C7 13.3(8) 2 . . . ?
C7 C2 C3 C4 -0.7(10) . . . . ?
C1 C2 C3 C4 179.6(6) . . . . ?
C4 C5 C6 C7 -1.6(10) . . . . ?
N4 C5 C6 C7 176.7(6) . . . . ?
C5 C6 C7 C2 3.3(10) . . . . ?
C3 C2 C7 C6 -2.2(9) . . . . ?
C1 C2 C7 C6 177.5(6) . . . . ?
C6 C5 C4 C3 -1.3(11) . . . . ?
N4 C5 C4 C3 -179.6(7) . . . . ?
C2 C3 C4 C5 2.4(12) . . . . ?
C4 C5 N4 N5 177.2(7) . . . . ?
C6 C5 N4 N5 -1.1(11) . . . . ?
Cu1 O3 C8 C9 -69.7(8) . . . . ?

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
_geom_hbond_publ_flag
O3 H7A N3 0.93 2.32 2.906(7) 120.9 2_655 yes

_refine_diff_density_max         1.033
_refine_diff_density_min         -1.854
_refine_diff_density_rms         0.524

