# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_EC-Cu1
_database_code_depnum_ccdc_archive 'CCDC 1845998'
loop_
_audit_author_name
_audit_author_address
'Qi Yang'
;Northwest University
China
;
_audit_update_record             
;
2023-10-31 deposited with the CCDC.	2023-11-03 downloaded from the CCDC.
;
_audit_creation_date             2023-10-20
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r1)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H8 Cu N18 O2'
_chemical_formula_sum            'C6 H8 Cu N18 O2'
_chemical_formula_weight         427.84
_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                   6.8830(18)
_cell_length_b                   9.131(3)
_cell_length_c                   12.186(3)
_cell_angle_alpha                101.122(4)
_cell_angle_beta                 103.119(5)
_cell_angle_gamma                106.744(4)
_cell_volume                     686.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    795
_cell_measurement_temperature    296
_cell_measurement_theta_max      24.55
_cell_measurement_theta_min      2.58
_shelx_estimated_absorpt_T_max   0.826
_shelx_estimated_absorpt_T_min   0.692
_exptl_absorpt_coefficient_mu    1.653
_exptl_absorpt_correction_T_max  0.7954
_exptl_absorpt_correction_T_min  0.6668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0576 before and 0.0359 after correction.
The Ratio of minimum to maximum transmission is 0.8677.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear bluish blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    2.070
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             430
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3418
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.424
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1799
_reflns_number_total             2381
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         2381
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.026
_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)+(0.0469P)²+0.1301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1057
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2. Restrained distances
 H1A-O1
 0.85 with sigma of 0.02
 H1B-O1
 0.85 with sigma of 0.02
 H2B-O2
 0.85 with sigma of 0.02
 H2A-O2
 0.85 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N9(H9), N13(H13), N14(H14), N8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.78407(9) 0.24799(7) 0.33136(5) 0.0231(2) Uani 1 1 d . . . . .
N11 N 0.6586(6) -0.7812(4) 0.0283(4) 0.0279(9) Uani 1 1 d . . . . .
N2 N 0.7943(6) 0.0332(4) 0.2380(3) 0.0172(8) Uani 1 1 d . . . . .
N4 N 1.0194(6) 0.3668(4) 0.2913(3) 0.0211(9) Uani 1 1 d . . . . .
N18 N 0.5296(6) 0.1372(4) 0.3602(3) 0.0210(9) Uani 1 1 d . . . . .
C5 C 0.4414(7) -0.0161(5) 0.3416(4) 0.0175(10) Uani 1 1 d . . . . .
N9 N 0.5920(6) -0.5842(4) 0.1136(3) 0.0216(9) Uani 1 1 d . . . . .
H9 H 0.5342 -0.5287 0.1517 0.026 Uiso 1 1 calc R . . . .
N16 N 0.2699(6) 0.0909(5) 0.4327(3) 0.0262(9) Uani 1 1 d . . . . .
N15 N 0.2781(6) -0.0529(4) 0.3837(3) 0.0227(9) Uani 1 1 d . . . . .
O1 O 0.7361(6) 0.4504(4) 0.3927(3) 0.0347(9) Uani 1 1 d D . . . .
N17 N 0.4188(6) 0.2051(4) 0.4194(3) 0.0240(9) Uani 1 1 d . . . . .
O2 O 1.0002(5) 0.2421(4) 0.5105(3) 0.0272(8) Uani 1 1 d D . . . .
N5 N 1.1090(6) 0.5268(4) 0.3242(4) 0.0297(10) Uani 1 1 d . . . . .
N13 N 0.8609(6) -0.3724(4) 0.0812(3) 0.0224(9) Uani 1 1 d . . . . .
H13 H 0.9626 -0.3575 0.0500 0.027 Uiso 1 1 calc R . . . .
N7 N 1.2749(6) 0.4332(4) 0.2122(3) 0.0242(9) Uani 1 1 d . . . . .
N6 N 1.2597(7) 0.5642(5) 0.2771(4) 0.0313(10) Uani 1 1 d . . . . .
N1 N 0.9575(6) -0.1067(4) 0.1219(3) 0.0220(9) Uani 1 1 d . . . . .
N12 N 0.7978(6) -0.6471(4) 0.0191(3) 0.0221(9) Uani 1 1 d . . . . .
C4 C 1.1238(7) 0.3154(5) 0.2235(4) 0.0200(10) Uani 1 1 d . . . . .
N14 N 0.5068(6) -0.1298(4) 0.2845(3) 0.0221(9) Uani 1 1 d . . . . .
H14 H 0.4358 -0.2266 0.2795 0.026 Uiso 1 1 calc R . . . .
N8 N 1.0819(6) 0.1585(4) 0.1710(3) 0.0226(9) Uani 1 1 d . . . . .
H8 H 1.1590 0.1414 0.1269 0.027 Uiso 1 1 calc R . . . .
N10 N 0.5354(6) -0.7441(4) 0.0856(4) 0.0270(9) Uani 1 1 d . . . . .
C2 C 0.9380(7) 0.0256(5) 0.1774(4) 0.0194(10) Uani 1 1 d . . . . .
C1 C 0.8297(7) -0.2394(5) 0.1325(4) 0.0183(10) Uani 1 1 d . . . . .
N3 N 0.6808(6) -0.2525(4) 0.1870(3) 0.0219(9) Uani 1 1 d . . . . .
C3 C 0.6663(7) -0.1116(5) 0.2352(4) 0.0176(9) Uani 1 1 d . . . . .
C6 C 0.7521(7) -0.5272(5) 0.0725(4) 0.0193(10) Uani 1 1 d . . . . .
H1A H 0.827(6) 0.543(3) 0.415(4) 0.043(17) Uiso 1 1 d D . . . .
H1B H 0.648(8) 0.429(7) 0.431(5) 0.06(2) Uiso 1 1 d D . . . .
H2A H 1.071(9) 0.184(7) 0.490(6) 0.08(2) Uiso 1 1 d D . . . .
H2B H 0.934(7) 0.200(5) 0.553(4) 0.030(14) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 2.098(3) . ?
Cu1 N4 1.894(3) . ?
Cu1 N18 1.901(3) . ?
Cu1 O1 2.004(4) . ?
Cu1 O2 2.367(4) . ?
N11 N12 1.362(5) . ?
N11 N10 1.289(5) . ?
N2 C2 1.371(5) . ?
N2 C3 1.350(5) . ?
N4 N5 1.349(5) . ?
N4 C4 1.317(5) . ?
N18 C5 1.306(5) . ?
N18 N17 1.355(5) . ?
C5 N15 1.323(5) . ?
C5 N14 1.377(5) . ?
N9 H9 0.8600 . ?
N9 N10 1.349(5) . ?
N9 C6 1.326(5) . ?
N16 N15 1.356(5) . ?
N16 N17 1.300(5) . ?
O1 H1A 0.85(2) . ?
O1 H1B 0.84(2) . ?
O2 H2A 0.85(2) . ?
O2 H2B 0.84(2) . ?
N5 N6 1.291(5) . ?
N13 H13 0.8600 . ?
N13 C1 1.353(5) . ?
N13 C6 1.366(5) . ?
N7 N6 1.346(5) . ?
N7 C4 1.318(5) . ?
N1 C2 1.325(5) . ?
N1 C1 1.326(5) . ?
N12 C6 1.318(5) . ?
C4 N8 1.367(5) . ?
N14 H14 0.8600 . ?
N14 C3 1.351(5) . ?
N8 H8 0.8600 . ?
N8 C2 1.356(6) . ?
C1 N3 1.332(5) . ?
N3 C3 1.349(5) . ?

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 O2 93.08(13) . . ?
N4 Cu1 N2 91.25(14) . . ?
N4 Cu1 N18 173.77(16) . . ?
N4 Cu1 O1 89.21(15) . . ?
N4 Cu1 O2 93.23(14) . . ?
N18 Cu1 N2 90.80(15) . . ?
N18 Cu1 O1 87.70(15) . . ?
N18 Cu1 O2 92.53(14) . . ?
O1 Cu1 N2 169.40(15) . . ?
O1 Cu1 O2 97.46(14) . . ?
N10 N11 N12 110.1(3) . . ?
C2 N2 Cu1 123.3(3) . . ?
C3 N2 Cu1 123.6(3) . . ?
C3 N2 C2 113.0(3) . . ?
N5 N4 Cu1 125.6(3) . . ?
C4 N4 Cu1 128.8(3) . . ?
C4 N4 N5 105.5(3) . . ?
C5 N18 Cu1 127.9(3) . . ?
C5 N18 N17 106.0(3) . . ?
N17 N18 Cu1 125.6(3) . . ?
N18 C5 N15 112.5(4) . . ?
N18 C5 N14 125.0(4) . . ?
N15 C5 N14 122.5(4) . . ?
N10 N9 H9 125.9 . . ?
C6 N9 H9 125.9 . . ?
C6 N9 N10 108.3(3) . . ?
N17 N16 N15 110.8(3) . . ?
C5 N15 N16 103.4(4) . . ?
Cu1 O1 H1A 126(4) . . ?
Cu1 O1 H1B 107(4) . . ?
H1A O1 H1B 118(5) . . ?
N16 N17 N18 107.4(3) . . ?
Cu1 O2 H2A 104(5) . . ?
Cu1 O2 H2B 115(3) . . ?
H2A O2 H2B 107(5) . . ?
N6 N5 N4 107.8(3) . . ?
C1 N13 H13 115.7 . . ?
C1 N13 C6 128.6(4) . . ?
C6 N13 H13 115.7 . . ?
C4 N7 N6 103.7(3) . . ?
N5 N6 N7 111.0(4) . . ?
C2 N1 C1 114.6(4) . . ?
C6 N12 N11 106.0(4) . . ?
N4 C4 N7 112.0(4) . . ?
N4 C4 N8 124.4(4) . . ?
N7 C4 N8 123.6(4) . . ?
C5 N14 H14 115.3 . . ?
C3 N14 C5 129.4(4) . . ?
C3 N14 H14 115.3 . . ?
C4 N8 H8 114.9 . . ?
C2 N8 C4 130.2(4) . . ?
C2 N8 H8 114.9 . . ?
N11 N10 N9 106.9(3) . . ?
N1 C2 N2 125.5(4) . . ?
N1 C2 N8 112.5(4) . . ?
N8 C2 N2 121.9(4) . . ?
N1 C1 N13 113.7(4) . . ?
N1 C1 N3 127.1(4) . . ?
N3 C1 N13 119.2(4) . . ?
C1 N3 C3 113.5(4) . . ?
N2 C3 N14 122.1(4) . . ?
N3 C3 N2 126.0(4) . . ?
N3 C3 N14 111.9(4) . . ?
N9 C6 N13 128.6(4) . . ?
N12 C6 N9 108.7(4) . . ?
N12 C6 N13 122.6(4) . . ?

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 N2 C2 N1 176.6(3) . . . . ?
Cu1 N2 C2 N8 -1.8(6) . . . . ?
Cu1 N2 C3 N14 6.0(6) . . . . ?
Cu1 N2 C3 N3 -172.6(3) . . . . ?
Cu1 N4 N5 N6 -177.8(3) . . . . ?
Cu1 N4 C4 N7 177.7(3) . . . . ?
Cu1 N4 C4 N8 -2.4(7) . . . . ?
Cu1 N18 C5 N15 172.8(3) . . . . ?
Cu1 N18 C5 N14 -7.5(7) . . . . ?
Cu1 N18 N17 N16 -172.7(3) . . . . ?
N11 N12 C6 N9 0.3(5) . . . . ?
N11 N12 C6 N13 179.7(4) . . . . ?
N2 Cu1 N4 N5 -179.9(4) . . . . ?
N2 Cu1 N4 C4 3.3(4) . . . . ?
N4 N5 N6 N7 0.2(5) . . . . ?
N4 C4 N8 C2 -2.2(8) . . . . ?
N18 C5 N15 N16 -0.7(5) . . . . ?
N18 C5 N14 C3 -1.1(7) . . . . ?
C5 N18 N17 N16 -0.5(5) . . . . ?
C5 N14 C3 N2 1.3(7) . . . . ?
C5 N14 C3 N3 -179.9(4) . . . . ?
N15 C5 N14 C3 178.6(4) . . . . ?
N15 N16 N17 N18 0.1(5) . . . . ?
O1 Cu1 N4 N5 10.7(4) . . . . ?
O1 Cu1 N4 C4 -166.1(4) . . . . ?
N17 N18 C5 N15 0.8(5) . . . . ?
N17 N18 C5 N14 -179.5(4) . . . . ?
N17 N16 N15 C5 0.4(5) . . . . ?
O2 Cu1 N4 N5 -86.7(4) . . . . ?
O2 Cu1 N4 C4 96.5(4) . . . . ?
N5 N4 C4 N7 0.4(5) . . . . ?
N5 N4 C4 N8 -179.7(4) . . . . ?
N13 C1 N3 C3 179.6(4) . . . . ?
N7 C4 N8 C2 177.7(4) . . . . ?
N6 N7 C4 N4 -0.2(5) . . . . ?
N6 N7 C4 N8 179.9(4) . . . . ?
N1 C1 N3 C3 -0.2(7) . . . . ?
N12 N11 N10 N9 0.6(5) . . . . ?
C4 N4 N5 N6 -0.4(5) . . . . ?
C4 N7 N6 N5 0.0(5) . . . . ?
C4 N8 C2 N2 4.2(7) . . . . ?
C4 N8 C2 N1 -174.3(4) . . . . ?
N14 C5 N15 N16 179.5(4) . . . . ?
N10 N11 N12 C6 -0.6(5) . . . . ?
N10 N9 C6 N13 -179.4(4) . . . . ?
N10 N9 C6 N12 0.0(5) . . . . ?
C2 N2 C3 N14 -176.5(4) . . . . ?
C2 N2 C3 N3 4.9(6) . . . . ?
C2 N1 C1 N13 -176.2(4) . . . . ?
C2 N1 C1 N3 3.5(7) . . . . ?
C1 N13 C6 N9 -1.1(8) . . . . ?
C1 N13 C6 N12 179.5(4) . . . . ?
C1 N1 C2 N2 -2.8(7) . . . . ?
C1 N1 C2 N8 175.6(4) . . . . ?
C1 N3 C3 N2 -4.4(6) . . . . ?
C1 N3 C3 N14 176.8(4) . . . . ?
C3 N2 C2 N1 -1.0(6) . . . . ?
C3 N2 C2 N8 -179.3(4) . . . . ?
C6 N9 N10 N11 -0.4(5) . . . . ?
C6 N13 C1 N1 -177.4(4) . . . . ?
C6 N13 C1 N3 2.8(7) . . . . ?

_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_EC-Cu2
_database_code_depnum_ccdc_archive 'CCDC 1848504'
loop_
_audit_author_name
_audit_author_address
'Qi Yang'
;Northwest University
China
;
_audit_update_record             
;
2023-10-31 deposited with the CCDC.	2023-11-03 downloaded from the CCDC.
;
_audit_creation_date             2023-10-19
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r1)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 Cu3 N36 O2'
_chemical_formula_sum            'C12 H10 Cu3 N36 O2'
_chemical_formula_weight         881.18
_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                   6.3422(11)
_cell_length_b                   7.9744(13)
_cell_length_c                   13.452(2)
_cell_angle_alpha                73.360(8)
_cell_angle_beta                 84.082(9)
_cell_angle_gamma                75.297(8)
_cell_volume                     630.15(18)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1748
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.74
_shelx_estimated_absorpt_T_max   0.818
_shelx_estimated_absorpt_T_min   0.597
_exptl_absorpt_coefficient_mu    2.611
_exptl_absorpt_correction_T_max  0.7151
_exptl_absorpt_correction_T_min  0.6031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0899 before and 0.0695 after correction.
The Ratio of minimum to maximum transmission is 0.2053.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear bluish blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    2.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             437
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0968
_diffrn_reflns_av_unetI/netI     0.0781
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10939
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.404
_diffrn_reflns_theta_min         2.743
_diffrn_ambient_temperature      150.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1659
_reflns_number_total             2531
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.907
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2531
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      1.012
_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)+(0.0757P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1447
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 N18(H2), N13(H3), N8(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Cu2 Cu 0.5000 0.5000 1.0000 0.0303(3) Uani 1 2 d S T P . .
Cu1 Cu 0.37295(13) 0.37166(10) 0.77078(6) 0.0327(3) Uani 1 1 d . . . . .
O1 O 0.3504(8) 0.2560(6) 1.0020(4) 0.0385(11) Uani 1 1 d . . . . .
H1A H 0.3751 0.2333 0.9417 0.058 Uiso 1 1 d GR . . . .
H1B H 0.2090 0.2880 1.0081 0.058 Uiso 1 1 d GR . . . .
N4 N 0.2829(8) 0.6075(6) 0.7953(4) 0.0276(11) Uani 1 1 d . . . . .
N14 N 0.3138(8) 0.6411(6) 0.1836(4) 0.0285(11) Uani 1 1 d . . . . .
N15 N 0.2782(9) 0.5782(7) 0.1051(4) 0.0301(12) Uani 1 1 d . . . . .
N5 N 0.2981(8) 0.6459(6) 0.8863(4) 0.0287(11) Uani 1 1 d . . . . .
N3 N 0.2628(8) 0.5094(7) 0.6035(4) 0.0288(11) Uani 1 1 d . . . . .
N18 N 0.0712(9) 0.7592(7) 0.3099(4) 0.0307(12) Uani 1 1 d . . . . .
H2 H -0.0051 0.8715 0.2968 0.037 Uiso 1 1 calc R . . . .
N2 N 0.2354(8) 0.5005(6) 0.4287(4) 0.0281(11) Uani 1 1 d . . . . .
N16 N 0.0705(9) 0.5831(7) 0.1034(4) 0.0317(12) Uani 1 1 d . . . . .
N13 N 0.3886(9) 0.2478(7) 0.5454(4) 0.0332(12) Uani 1 1 d . . . . .
H3 H 0.4031 0.2052 0.4909 0.040 Uiso 1 1 calc R . . . .
N9 N 0.4682(9) 0.1502(6) 0.7292(4) 0.0300(11) Uani 1 1 d . . . . .
N1 N 0.0939(9) 0.7758(7) 0.4744(4) 0.0312(12) Uani 1 1 d . . . . .
N8 N 0.1111(9) 0.7921(7) 0.6357(4) 0.0317(12) Uani 1 1 d . . . . .
H1 H 0.0279 0.9001 0.6104 0.038 Uiso 1 1 calc R . . . .
N17 N -0.0346(9) 0.6462(7) 0.1809(4) 0.0304(12) Uani 1 1 d . . . . .
N7 N 0.1132(9) 0.8866(7) 0.7861(4) 0.0322(12) Uani 1 1 d . . . . .
N10 N 0.5689(9) -0.0126(7) 0.7912(4) 0.0315(12) Uani 1 1 d . . . . .
N6 N 0.1970(9) 0.8123(7) 0.8797(4) 0.0338(12) Uani 1 1 d . . . . .
N11 N 0.6215(9) -0.1280(7) 0.7368(4) 0.0354(13) Uani 1 1 d . . . . .
N12 N 0.5611(9) -0.0484(7) 0.6373(4) 0.0324(12) Uani 1 1 d . . . . .
C5 C 0.4683(10) 0.1213(8) 0.6356(5) 0.0308(14) Uani 1 1 d . . . . .
C3 C 0.2916(10) 0.4267(8) 0.5260(5) 0.0306(14) Uani 1 1 d . . . . .
C6 C 0.1170(11) 0.6797(8) 0.2281(5) 0.0298(13) Uani 1 1 d . . . . .
C2 C 0.1584(10) 0.6875(8) 0.5688(5) 0.0310(14) Uani 1 1 d . . . . .
C4 C 0.1705(10) 0.7585(8) 0.7362(5) 0.0317(14) Uani 1 1 d . . . . .
C1 C 0.1350(10) 0.6770(9) 0.4070(5) 0.0319(14) 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
Cu2 O1 2.364(4) . ?
Cu2 O1 2.364(4) 2_667 ?
Cu2 N15 2.004(5) 1_556 ?
Cu2 N15 2.004(5) 2_666 ?
Cu2 N5 1.990(5) . ?
Cu2 N5 1.990(5) 2_667 ?
Cu1 N4 1.935(5) . ?
Cu1 N14 2.109(5) 2_666 ?
Cu1 N3 2.297(5) . ?
Cu1 N9 1.937(5) . ?
Cu1 N17 2.205(5) 2_566 ?
O1 H1A 0.8704 . ?
O1 H1B 0.8700 . ?
N4 N5 1.362(6) . ?
N4 C4 1.313(8) . ?
N14 Cu1 2.109(5) 2_666 ?
N14 N15 1.351(6) . ?
N14 C6 1.329(8) . ?
N15 Cu2 2.004(5) 1_554 ?
N15 N16 1.310(7) . ?
N5 N6 1.301(7) . ?
N3 C3 1.359(7) . ?
N3 C2 1.372(8) . ?
N18 H2 0.8800 . ?
N18 C6 1.393(7) . ?
N18 C1 1.335(8) . ?
N2 C3 1.318(8) . ?
N2 C1 1.349(8) . ?
N16 N17 1.332(6) . ?
N13 H3 0.8800 . ?
N13 C5 1.383(8) . ?
N13 C3 1.363(7) . ?
N9 N10 1.363(7) . ?
N9 C5 1.344(8) . ?
N1 C2 1.312(8) . ?
N1 C1 1.329(7) . ?
N8 H1 0.8800 . ?
N8 C2 1.358(7) . ?
N8 C4 1.374(8) . ?
N17 Cu1 2.205(5) 2_566 ?
N17 C6 1.323(8) . ?
N7 N6 1.331(7) . ?
N7 C4 1.334(7) . ?
N10 N11 1.293(7) . ?
N11 N12 1.356(8) . ?
N12 C5 1.326(8) . ?

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 Cu2 O1 180.0 2_667 . ?
N15 Cu2 O1 92.69(18) 2_666 2_667 ?
N15 Cu2 O1 87.31(18) 2_666 . ?
N15 Cu2 O1 92.69(18) 1_556 . ?
N15 Cu2 O1 87.31(18) 1_556 2_667 ?
N15 Cu2 N15 180.0 2_666 1_556 ?
N5 Cu2 O1 93.29(18) . 2_667 ?
N5 Cu2 O1 86.71(18) 2_667 2_667 ?
N5 Cu2 O1 86.71(18) . . ?
N5 Cu2 O1 93.29(18) 2_667 . ?
N5 Cu2 N15 89.7(2) . 2_666 ?
N5 Cu2 N15 89.7(2) 2_667 1_556 ?
N5 Cu2 N15 90.3(2) 2_667 2_666 ?
N5 Cu2 N15 90.3(2) . 1_556 ?
N5 Cu2 N5 180.0 . 2_667 ?
N4 Cu1 N14 87.3(2) . 2_666 ?
N4 Cu1 N3 87.03(19) . . ?
N4 Cu1 N9 173.2(2) . . ?
N4 Cu1 N17 84.7(2) . 2_566 ?
N14 Cu1 N3 121.83(19) 2_666 . ?
N14 Cu1 N17 147.3(2) 2_666 2_566 ?
N9 Cu1 N14 93.4(2) . 2_666 ?
N9 Cu1 N3 86.91(19) . . ?
N9 Cu1 N17 98.2(2) . 2_566 ?
N17 Cu1 N3 89.38(19) 2_566 . ?
Cu2 O1 H1A 109.2 . . ?
Cu2 O1 H1B 109.4 . . ?
H1A O1 H1B 104.5 . . ?
N5 N4 Cu1 125.9(4) . . ?
C4 N4 Cu1 129.1(4) . . ?
C4 N4 N5 104.4(5) . . ?
N15 N14 Cu1 123.7(4) . 2_666 ?
C6 N14 Cu1 132.0(4) . 2_666 ?
C6 N14 N15 103.5(5) . . ?
N14 N15 Cu2 126.6(4) . 1_554 ?
N16 N15 Cu2 123.4(4) . 1_554 ?
N16 N15 N14 109.9(4) . . ?
N4 N5 Cu2 126.5(4) . . ?
N6 N5 Cu2 122.2(4) . . ?
N6 N5 N4 109.6(5) . . ?
C3 N3 Cu1 125.0(4) . . ?
C3 N3 C2 111.0(5) . . ?
C2 N3 Cu1 124.0(4) . . ?
C6 N18 H2 117.7 . . ?
C1 N18 H2 117.7 . . ?
C1 N18 C6 124.6(5) . . ?
C3 N2 C1 114.4(5) . . ?
N15 N16 N17 109.0(5) . . ?
C5 N13 H3 114.3 . . ?
C3 N13 H3 114.3 . . ?
C3 N13 C5 131.3(5) . . ?
N10 N9 Cu1 125.4(4) . . ?
C5 N9 Cu1 129.9(4) . . ?
C5 N9 N10 104.5(5) . . ?
C2 N1 C1 114.6(5) . . ?
C2 N8 H1 114.4 . . ?
C2 N8 C4 131.2(6) . . ?
C4 N8 H1 114.4 . . ?
N16 N17 Cu1 122.1(4) . 2_566 ?
C6 N17 Cu1 131.2(4) . 2_566 ?
C6 N17 N16 105.2(5) . . ?
N6 N7 C4 105.8(5) . . ?
N11 N10 N9 108.9(5) . . ?
N5 N6 N7 108.8(4) . . ?
N10 N11 N12 110.5(5) . . ?
C5 N12 N11 104.4(5) . . ?
N9 C5 N13 126.6(5) . . ?
N12 C5 N13 121.7(5) . . ?
N12 C5 N9 111.7(6) . . ?
N3 C3 N13 120.1(6) . . ?
N2 C3 N3 127.2(5) . . ?
N2 C3 N13 112.7(5) . . ?
N14 C6 N18 124.1(6) . . ?
N17 C6 N14 112.3(5) . . ?
N17 C6 N18 123.3(6) . . ?
N1 C2 N3 127.4(5) . . ?
N1 C2 N8 112.9(5) . . ?
N8 C2 N3 119.7(6) . . ?
N4 C4 N8 127.8(5) . . ?
N4 C4 N7 111.4(6) . . ?
N7 C4 N8 120.8(6) . . ?
N18 C1 N2 117.3(5) . . ?
N1 C1 N18 117.3(6) . . ?
N1 C1 N2 125.4(6) . . ?

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 N15 N16 N17 -178.0(4) 1_554 . . . ?
Cu2 N5 N6 N7 166.6(4) . . . . ?
Cu1 N4 N5 Cu2 22.7(7) . . . . ?
Cu1 N4 N5 N6 -171.7(4) . . . . ?
Cu1 N4 C4 N8 -8.8(10) . . . . ?
Cu1 N4 C4 N7 170.8(4) . . . . ?
Cu1 N14 N15 Cu2 -11.2(7) 2_666 . . 1_554 ?
Cu1 N14 N15 N16 171.9(4) 2_666 . . . ?
Cu1 N14 C6 N18 14.2(9) 2_666 . . . ?
Cu1 N14 C6 N17 -170.5(4) 2_666 . . . ?
Cu1 N3 C3 N2 -178.5(5) . . . . ?
Cu1 N3 C3 N13 1.3(8) . . . . ?
Cu1 N3 C2 N1 178.9(5) . . . . ?
Cu1 N3 C2 N8 -1.3(8) . . . . ?
Cu1 N9 N10 N11 -176.1(4) . . . . ?
Cu1 N9 C5 N13 -3.0(10) . . . . ?
Cu1 N9 C5 N12 175.6(4) . . . . ?
Cu1 N17 C6 N14 166.5(4) 2_566 . . . ?
Cu1 N17 C6 N18 -18.1(9) 2_566 . . . ?
N4 N5 N6 N7 0.2(7) . . . . ?
N14 N15 N16 N17 -0.9(7) . . . . ?
N15 N14 C6 N18 -176.1(5) . . . . ?
N15 N14 C6 N17 -0.7(7) . . . . ?
N15 N16 N17 Cu1 -167.4(4) . . . 2_566 ?
N15 N16 N17 C6 0.4(6) . . . . ?
N5 N4 C4 N8 179.5(6) . . . . ?
N5 N4 C4 N7 -0.9(7) . . . . ?
N16 N17 C6 N14 0.2(7) . . . . ?
N16 N17 C6 N18 175.6(6) . . . . ?
N9 N10 N11 N12 0.6(7) . . . . ?
N10 N9 C5 N13 -178.2(6) . . . . ?
N10 N9 C5 N12 0.4(7) . . . . ?
N10 N11 N12 C5 -0.3(7) . . . . ?
N6 N7 C4 N4 1.0(7) . . . . ?
N6 N7 C4 N8 -179.3(6) . . . . ?
N11 N12 C5 N13 178.6(6) . . . . ?
N11 N12 C5 N9 -0.1(7) . . . . ?
C5 N13 C3 N3 1.0(11) . . . . ?
C5 N13 C3 N2 -179.1(6) . . . . ?
C5 N9 N10 N11 -0.6(7) . . . . ?
C3 N3 C2 N1 -1.1(9) . . . . ?
C3 N3 C2 N8 178.7(6) . . . . ?
C3 N2 C1 N18 -179.1(5) . . . . ?
C3 N2 C1 N1 0.7(9) . . . . ?
C3 N13 C5 N9 -0.5(11) . . . . ?
C3 N13 C5 N12 -179.0(6) . . . . ?
C6 N14 N15 Cu2 177.9(4) . . . 1_554 ?
C6 N14 N15 N16 1.0(6) . . . . ?
C6 N18 C1 N2 -5.6(9) . . . . ?
C6 N18 C1 N1 174.6(6) . . . . ?
C2 N3 C3 N2 1.5(9) . . . . ?
C2 N3 C3 N13 -178.7(6) . . . . ?
C2 N1 C1 N18 179.4(6) . . . . ?
C2 N1 C1 N2 -0.4(9) . . . . ?
C2 N8 C4 N4 -3.9(11) . . . . ?
C2 N8 C4 N7 176.4(6) . . . . ?
C4 N4 N5 Cu2 -165.3(4) . . . . ?
C4 N4 N5 N6 0.4(7) . . . . ?
C4 N8 C2 N3 8.3(10) . . . . ?
C4 N8 C2 N1 -171.8(6) . . . . ?
C4 N7 N6 N5 -0.7(7) . . . . ?
C1 N18 C6 N14 -71.1(9) . . . . ?
C1 N18 C6 N17 114.1(7) . . . . ?
C1 N2 C3 N3 -1.3(9) . . . . ?
C1 N2 C3 N13 178.8(5) . . . . ?
C1 N1 C2 N3 0.7(9) . . . . ?
C1 N1 C2 N8 -179.2(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
