# 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_cu22
_audit_block_doi                 10.5517/ccdc.csd.cc21zw75
_database_code_depnum_ccdc_archive 'CCDC 1906507'
loop_
_audit_author_name
_audit_author_address
'Cu two hydroxy aroylhydrazone'
;Guangdong Institute of Microbiology
China
;
_audit_update_record             
;
2019-11-25 deposited with the CCDC.	2019-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H22 Cu N8 O4'
_chemical_formula_sum            'C26 H22 Cu N8 O4'
_chemical_formula_weight         574.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_H-M_alt        'A b a 2'
_space_group_name_Hall           'A 2 -2ac'

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

_cell_length_a                   12.6731(10)
_cell_length_b                   18.9500(13)
_cell_length_c                   10.0490(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2413.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    831
_cell_measurement_theta_min      3.9610
_cell_measurement_theta_max      23.4440

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_F_000             1180
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    0.958
_shelx_estimated_absorpt_T_min   0.646
_shelx_estimated_absorpt_T_max   0.701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_reflns_number            2750
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.215
_diffrn_reflns_theta_max         25.468
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.757
_diffrn_reflns_point_group_measured_fraction_full 0.769
_reflns_number_total             1695
_reflns_number_gt                1367
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.495
_reflns_Friedel_fraction_max     0.535
_reflns_Friedel_fraction_full    0.550

_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 FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (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)+(0.0192P)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_abs_structure_details 
;
 Flack x determined using 388 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.043(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1695
_refine_ls_number_parameters     179
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0683
_refine_ls_wR_factor_gt          0.0626
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.0434(5) 0.8942(3) 0.2376(8) 0.060(2) Uani 1 1 d . . . . .
H1 H -0.028606 0.884857 0.234210 0.072 Uiso 1 1 calc R U . . .
C2 C 0.1101(7) 0.8613(3) 0.1490(7) 0.069(2) Uani 1 1 d . . . . .
H2 H 0.081263 0.830078 0.087532 0.083 Uiso 1 1 calc R U . . .
C3 C 0.2514(7) 0.9168(2) 0.2381(8) 0.0497(14) Uani 1 1 d . . . . .
H3 H 0.323568 0.925477 0.241103 0.060 Uiso 1 1 calc R U . . .
C4 C 0.1852(4) 0.9511(3) 0.3288(6) 0.0358(14) Uani 1 1 d . . . . .
C5 C 0.2221(4) 1.0022(3) 0.4275(5) 0.0371(13) Uani 1 1 d . . . . .
C6 C 0.3368(5) 1.0195(3) 0.4458(6) 0.0543(19) Uani 1 1 d . . . . .
H6A H 0.344937 1.069638 0.455413 0.081 Uiso 1 1 calc R U . . .
H6B H 0.375829 1.003716 0.369592 0.081 Uiso 1 1 calc R U . . .
H6C H 0.362823 0.996332 0.524104 0.081 Uiso 1 1 calc R U . . .
C7 C -0.0829(5) 0.8925(3) 0.6456(6) 0.0398(14) Uani 1 1 d . . . . .
C8 C -0.1015(4) 0.8350(3) 0.7452(6) 0.0363(14) Uani 1 1 d . . . . .
C9 C -0.2033(5) 0.8143(3) 0.7867(6) 0.0417(16) Uani 1 1 d . . . . .
C10 C -0.2123(5) 0.7651(3) 0.8879(6) 0.0541(18) Uani 1 1 d . . . . .
H10 H -0.278940 0.753015 0.919166 0.065 Uiso 1 1 calc R U . . .
C11 C -0.1256(5) 0.7341(3) 0.9427(6) 0.0531(18) Uani 1 1 d . . . . .
H11 H -0.133167 0.700970 1.010368 0.064 Uiso 1 1 calc R U . . .
C12 C -0.0264(5) 0.7522(3) 0.8971(6) 0.0516(17) Uani 1 1 d . . . . .
H12 H 0.033002 0.730420 0.932700 0.062 Uiso 1 1 calc R U . . .
C13 C -0.0152(5) 0.8015(3) 0.8007(6) 0.0440(15) Uani 1 1 d . . . . .
H13 H 0.052127 0.813204 0.771230 0.053 Uiso 1 1 calc R U . . .
Cu1 Cu 0.000000 1.000000 0.48327(11) 0.0420(3) Uani 1 2 d S T P . .
N1 N 0.0804(4) 0.9392(2) 0.3279(5) 0.0417(12) Uani 1 1 d . . . . .
N2 N 0.2136(5) 0.8719(3) 0.1471(6) 0.0640(17) Uani 1 1 d . . . . .
N3 N 0.1486(3) 1.03160(19) 0.4942(6) 0.0385(11) Uani 1 1 d . . . . .
N4 N 0.1732(4) 1.0833(2) 0.5872(4) 0.0439(13) Uani 1 1 d . . . . .
O1 O 0.0067(3) 0.91567(18) 0.6231(4) 0.0435(10) Uani 1 1 d . . . . .
O2 O -0.2924(3) 0.8426(2) 0.7376(5) 0.0660(14) Uani 1 1 d . . . . .
H2A H -0.277458 0.872500 0.681651 0.099 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
C1 N1 1.331(8) . ?
C1 C2 1.377(9) . ?
C1 H1 0.9300 . ?
C2 N2 1.327(10) . ?
C2 H2 0.9300 . ?
C3 N2 1.337(8) . ?
C3 C4 1.399(8) . ?
C3 H3 0.9300 . ?
C4 N1 1.346(7) . ?
C4 C5 1.463(7) . ?
C5 N3 1.276(6) . ?
C5 C6 1.501(7) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 O1 1.238(7) . ?
C7 N4 1.365(7) 2_575 ?
C7 C8 1.499(7) . ?
C8 C13 1.381(8) . ?
C8 C9 1.411(8) . ?
C9 O2 1.344(6) . ?
C9 C10 1.385(7) . ?
C10 C11 1.362(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.353(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
Cu1 N3 1.979(4) . ?
Cu1 N3 1.979(4) 2_575 ?
Cu1 O1 2.130(3) . ?
Cu1 O1 2.130(3) 2_575 ?
Cu1 N1 2.192(5) 2_575 ?
Cu1 N1 2.192(5) . ?
N3 N4 1.389(5) . ?
O2 H2A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.0(7) . . ?
N1 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
N2 C2 C1 123.2(7) . . ?
N2 C2 H2 118.4 . . ?
C1 C2 H2 118.4 . . ?
N2 C3 C4 121.7(7) . . ?
N2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
N1 C4 C3 120.6(6) . . ?
N1 C4 C5 115.5(5) . . ?
C3 C4 C5 123.9(6) . . ?
N3 C5 C4 114.3(5) . . ?
N3 C5 C6 123.2(5) . . ?
C4 C5 C6 122.5(5) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 N4 124.8(5) . 2_575 ?
O1 C7 C8 121.6(6) . . ?
N4 C7 C8 113.6(5) 2_575 . ?
C13 C8 C9 118.5(5) . . ?
C13 C8 C7 118.7(5) . . ?
C9 C8 C7 122.8(5) . . ?
O2 C9 C10 118.0(6) . . ?
O2 C9 C8 123.3(5) . . ?
C10 C9 C8 118.6(6) . . ?
C11 C10 C9 121.4(6) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 119.5(6) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 120.3(6) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 121.5(6) . . ?
C12 C13 H13 119.2 . . ?
C8 C13 H13 119.2 . . ?
N3 Cu1 N3 173.6(4) . 2_575 ?
N3 Cu1 O1 98.79(18) . . ?
N3 Cu1 O1 76.94(18) 2_575 . ?
N3 Cu1 O1 76.94(18) . 2_575 ?
N3 Cu1 O1 98.79(18) 2_575 2_575 ?
O1 Cu1 O1 97.4(2) . 2_575 ?
N3 Cu1 N1 108.8(2) . 2_575 ?
N3 Cu1 N1 75.9(2) 2_575 2_575 ?
O1 Cu1 N1 151.98(17) . 2_575 ?
O1 Cu1 N1 93.28(16) 2_575 2_575 ?
N3 Cu1 N1 75.9(2) . . ?
N3 Cu1 N1 108.8(2) 2_575 . ?
O1 Cu1 N1 93.28(16) . . ?
O1 Cu1 N1 151.98(17) 2_575 . ?
N1 Cu1 N1 89.1(2) 2_575 . ?
C1 N1 C4 117.3(5) . . ?
C1 N1 Cu1 131.2(5) . . ?
C4 N1 Cu1 111.5(4) . . ?
C2 N2 C3 116.2(6) . . ?
C5 N3 N4 119.8(5) . . ?
C5 N3 Cu1 122.3(4) . . ?
N4 N3 Cu1 117.7(4) . . ?
C7 N4 N3 109.7(5) 2_575 . ?
C7 O1 Cu1 110.5(4) . . ?
C9 O2 H2A 109.5 . . ?

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
N1 C1 C2 N2 -0.2(11) . . . . ?
N2 C3 C4 N1 0.7(8) . . . . ?
N2 C3 C4 C5 -178.1(5) . . . . ?
N1 C4 C5 N3 -3.9(6) . . . . ?
C3 C4 C5 N3 174.9(5) . . . . ?
N1 C4 C5 C6 177.5(5) . . . . ?
C3 C4 C5 C6 -3.7(7) . . . . ?
O1 C7 C8 C13 -7.9(7) . . . . ?
N4 C7 C8 C13 173.6(5) 2_575 . . . ?
O1 C7 C8 C9 170.8(5) . . . . ?
N4 C7 C8 C9 -7.6(7) 2_575 . . . ?
C13 C8 C9 O2 -179.0(5) . . . . ?
C7 C8 C9 O2 2.3(9) . . . . ?
C13 C8 C9 C10 4.5(8) . . . . ?
C7 C8 C9 C10 -174.2(5) . . . . ?
O2 C9 C10 C11 180.0(6) . . . . ?
C8 C9 C10 C11 -3.3(9) . . . . ?
C9 C10 C11 C12 0.3(9) . . . . ?
C10 C11 C12 C13 1.5(9) . . . . ?
C11 C12 C13 C8 -0.1(8) . . . . ?
C9 C8 C13 C12 -2.9(8) . . . . ?
C7 C8 C13 C12 175.9(5) . . . . ?
C2 C1 N1 C4 0.1(8) . . . . ?
C2 C1 N1 Cu1 -179.5(4) . . . . ?
C3 C4 N1 C1 -0.3(8) . . . . ?
C5 C4 N1 C1 178.6(5) . . . . ?
C3 C4 N1 Cu1 179.4(4) . . . . ?
C5 C4 N1 Cu1 -1.8(5) . . . . ?
C1 C2 N2 C3 0.5(10) . . . . ?
C4 C3 N2 C2 -0.7(9) . . . . ?
C4 C5 N3 N4 -177.4(4) . . . . ?
C6 C5 N3 N4 1.2(8) . . . . ?
C4 C5 N3 Cu1 8.7(6) . . . . ?
C6 C5 N3 Cu1 -172.7(4) . . . . ?
C5 N3 N4 C7 179.6(5) . . . 2_575 ?
Cu1 N3 N4 C7 -6.2(5) . . . 2_575 ?
N4 C7 O1 Cu1 1.0(7) 2_575 . . . ?
C8 C7 O1 Cu1 -177.2(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
_geom_hbond_publ_flag
C1 H1 O2 0.93 2.41 3.328(8) 171.1 8_444 yes
C3 H3 O1 0.93 2.46 3.277(9) 146.1 8_544 yes
O2 H2A N4 0.82 1.83 2.557(6) 147.0 2_575 yes

_refine_diff_density_max         0.490
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_cu23
_audit_block_doi                 10.5517/ccdc.csd.cc22499v
_database_code_depnum_ccdc_archive 'CCDC 1910756'
loop_
_audit_author_name
_audit_author_address
'Cu three hydroxy aroylhydrazone'
;Guangdong Institute of Microbiology
China
;
_audit_update_record             
;
2019-11-25 deposited with the CCDC.	2019-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H22 Cu N8 O4, 2(C3 H7 N O)'
_chemical_formula_sum            'C32 H36 Cu N10 O6'
_chemical_formula_weight         720.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   11.7488(3)
_cell_length_b                   9.2765(3)
_cell_length_c                   31.8767(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3474.17(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4325
_cell_measurement_theta_min      4.6460
_cell_measurement_theta_max      62.9290

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             1500
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    1.373
_shelx_estimated_absorpt_T_min   0.547
_shelx_estimated_absorpt_T_max   0.610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83481
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_reflns_number            10979
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         4.676
_diffrn_reflns_theta_max         62.768
_diffrn_reflns_theta_full        62.768
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2781
_reflns_number_gt                2363
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (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)+(0.0610P)²+0.8320P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00087(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2781
_refine_ls_number_parameters     265
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.070
_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
C1 C 1.0180(2) -0.1334(3) 0.32133(9) 0.0640(6) Uani 1 1 d . . . . .
H1 H 0.939152 -0.131231 0.323777 0.077 Uiso 1 1 calc R U . . .
C2 C 1.0792(3) -0.2222(3) 0.34698(9) 0.0748(8) Uani 1 1 d . . . . .
H2 H 1.040870 -0.277992 0.366655 0.090 Uiso 1 1 calc R U . . .
C3 C 1.2426(2) -0.1479(2) 0.31623(7) 0.0576(6) Uani 1 1 d . . . . .
H3 H 1.321413 -0.151613 0.313710 0.069 Uiso 1 1 calc R U . . .
C4 C 1.18229(16) -0.0560(2) 0.29026(6) 0.0434(4) Uani 1 1 d . . . . .
C5 C 0.76659(17) 0.0355(2) 0.24218(6) 0.0433(5) Uani 1 1 d . . . . .
C6 C 0.64188(19) 0.0406(3) 0.24955(7) 0.0561(6) Uani 1 1 d . . . . .
H6A H 0.627396 0.067317 0.278150 0.084 Uiso 1 1 calc R U . . .
H6B H 0.609544 -0.052602 0.244129 0.084 Uiso 1 1 calc R U . . .
H6C H 0.608049 0.110372 0.231131 0.084 Uiso 1 1 calc R U . . .
C7 C 0.88857(16) 0.2532(2) 0.31614(6) 0.0432(4) Uani 1 1 d . . . . .
C8 C 0.86318(18) 0.3260(2) 0.35674(6) 0.0481(5) Uani 1 1 d . . . . .
C9 C 0.9425(2) 0.4186(2) 0.37396(7) 0.0570(6) Uani 1 1 d . . . . .
H9 H 1.009647 0.437708 0.359540 0.068 Uiso 1 1 calc R U . . .
C10 C 0.9231(3) 0.4835(3) 0.41252(7) 0.0670(7) Uani 1 1 d . . . . .
C11 C 0.8240(3) 0.4549(3) 0.43376(8) 0.0794(8) Uani 1 1 d . . . . .
H11 H 0.810147 0.498425 0.459532 0.095 Uiso 1 1 calc R U . . .
C12 C 0.7454(3) 0.3617(4) 0.41690(9) 0.0799(8) Uani 1 1 d . . . . .
H12 H 0.678852 0.342119 0.431645 0.096 Uiso 1 1 calc R U . . .
C13 C 0.7632(2) 0.2967(3) 0.37845(8) 0.0637(6) Uani 1 1 d . . . . .
H13 H 0.709164 0.234346 0.367270 0.076 Uiso 1 1 calc R U . . .
Cu1 Cu 1.000000 0.11125(4) 0.250000 0.04277(18) Uani 1 2 d S T P . .
N1 N 1.06792(14) -0.0508(2) 0.29320(6) 0.0503(4) Uani 1 1 d . . . . .
N2 N 1.1921(2) -0.2313(2) 0.34471(7) 0.0737(6) Uani 1 1 d . . . . .
N3 N 0.83857(14) 0.10945(17) 0.26406(6) 0.0423(4) Uani 1 1 d . . . . .
N4 N 0.80109(14) 0.18758(18) 0.29787(5) 0.0472(4) Uani 1 1 d . . . . .
O1 O 0.98987(11) 0.25672(17) 0.30229(5) 0.0490(4) Uani 1 1 d . . . . .
O2 O 1.0059(2) 0.5729(3) 0.42745(7) 0.0978(8) Uani 1 1 d . . . . .
H2A H 0.986322 0.605549 0.450241 0.147 Uiso 1 1 calc R U . . .
N5 N 0.4024(3) 0.6578(3) 0.44848(8) 0.0915(8) Uani 0.788(11) 1 d . . P A 1
O3 O 0.4591(8) 0.7701(9) 0.50604(18) 0.144(3) Uani 0.788(11) 1 d . U P A 1
C14 C 0.4660(7) 0.7145(7) 0.47480(14) 0.115(2) Uani 0.788(11) 1 d . . P A 1
H14 H 0.541540 0.709452 0.466174 0.139 Uiso 0.788(11) 1 calc R U P A 1
C15 C 0.2795(7) 0.6775(15) 0.4524(3) 0.195(5) Uani 0.788(11) 1 d . . P A 1
H15A H 0.262523 0.721392 0.478944 0.293 Uiso 0.788(11) 1 calc R U P A 1
H15B H 0.242334 0.585486 0.450677 0.293 Uiso 0.788(11) 1 calc R U P A 1
H15C H 0.252780 0.738483 0.430149 0.293 Uiso 0.788(11) 1 calc R U P A 1
C16 C 0.4361(9) 0.5806(8) 0.4111(2) 0.139(3) Uani 0.788(11) 1 d . . P A 1
H16A H 0.517589 0.581437 0.408756 0.208 Uiso 0.788(11) 1 calc R U P A 1
H16B H 0.403351 0.626184 0.386933 0.208 Uiso 0.788(11) 1 calc R U P A 1
H16C H 0.409831 0.482761 0.412835 0.208 Uiso 0.788(11) 1 calc R U P A 1
N5A N 0.4024(3) 0.6578(3) 0.44848(8) 0.0915(8) Uani 0.212(11) 1 d D . P A 2
O3A O 0.395(2) 0.812(2) 0.5017(6) 0.107(6) Uani 0.212(11) 1 d D U P A 2
C14A C 0.374(4) 0.747(4) 0.4725(10) 0.27(4) Uani 0.212(11) 1 d D . P A 2
H14A H 0.302597 0.777364 0.463818 0.325 Uiso 0.212(11) 1 calc R U P A 2
C15A C 0.340(5) 0.613(6) 0.4168(9) 0.24(3) Uani 0.212(11) 1 d . . P A 2
H15D H 0.329430 0.511022 0.418862 0.358 Uiso 0.212(11) 1 calc R U P A 2
H15E H 0.378616 0.635505 0.390975 0.358 Uiso 0.212(11) 1 calc R U P A 2
H15F H 0.267890 0.660886 0.417406 0.358 Uiso 0.212(11) 1 calc R U P A 2
C16A C 0.515(3) 0.569(3) 0.4460(13) 0.178(16) Uani 0.212(11) 1 d . . P A 2
H16D H 0.558085 0.599610 0.422154 0.268 Uiso 0.212(11) 1 calc R U P A 2
H16E H 0.496558 0.468342 0.443251 0.268 Uiso 0.212(11) 1 calc R U P A 2
H16F H 0.558142 0.583701 0.471115 0.268 Uiso 0.212(11) 1 calc R U P A 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
C1 N1 1.317(3) . ?
C1 C2 1.365(4) . ?
C2 N2 1.331(4) . ?
C3 N2 1.332(3) . ?
C3 C4 1.384(3) . ?
C4 N1 1.348(3) . ?
C4 C5 1.466(3) 3_755 ?
C5 N3 1.293(3) . ?
C5 C6 1.485(3) . ?
C7 O1 1.270(2) . ?
C7 N4 1.329(3) . ?
C7 C8 1.490(3) . ?
C8 C9 1.382(3) . ?
C8 C13 1.390(3) . ?
C9 C10 1.387(3) . ?
C10 O2 1.364(3) . ?
C10 C11 1.373(4) . ?
C11 C12 1.375(5) . ?
C12 C13 1.382(4) . ?
Cu1 N3 1.9489(16) . ?
Cu1 N3 1.9489(16) 3_755 ?
Cu1 O1 2.1479(15) . ?
Cu1 O1 2.1480(15) 3_755 ?
Cu1 N1 2.1890(18) 3_755 ?
Cu1 N1 2.1890(18) . ?
N3 N4 1.372(2) . ?
N5 C14 1.240(6) . ?
N5 C16 1.445(7) . ?
N5 C15 1.462(8) . ?
O3 C14 1.125(8) . ?
N5A C14A 1.17(3) . ?
N5A C15A 1.31(4) . ?
N5A C16A 1.56(3) . ?
O3A C14A 1.14(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.6(2) . . ?
N2 C2 C1 122.1(2) . . ?
N2 C3 C4 122.5(2) . . ?
N1 C4 C3 119.4(2) . . ?
N1 C4 C5 115.88(18) . 3_755 ?
C3 C4 C5 124.67(19) . 3_755 ?
N3 C5 C4 114.80(17) . 3_755 ?
N3 C5 C6 122.90(19) . . ?
C4 C5 C6 122.29(18) 3_755 . ?
O1 C7 N4 125.76(18) . . ?
O1 C7 C8 118.56(18) . . ?
N4 C7 C8 115.68(17) . . ?
C9 C8 C13 119.6(2) . . ?
C9 C8 C7 119.47(18) . . ?
C13 C8 C7 120.9(2) . . ?
C8 C9 C10 120.8(2) . . ?
O2 C10 C11 123.4(2) . . ?
O2 C10 C9 117.1(2) . . ?
C11 C10 C9 119.5(3) . . ?
C10 C11 C12 119.9(2) . . ?
C11 C12 C13 121.3(2) . . ?
C12 C13 C8 119.0(3) . . ?
N3 Cu1 N3 179.02(10) . 3_755 ?
N3 Cu1 O1 76.88(6) . . ?
N3 Cu1 O1 103.75(6) 3_755 . ?
N3 Cu1 O1 103.75(6) . 3_755 ?
N3 Cu1 O1 76.88(6) 3_755 3_755 ?
O1 Cu1 O1 102.16(9) . 3_755 ?
N3 Cu1 N1 77.53(7) . 3_755 ?
N3 Cu1 N1 101.78(7) 3_755 3_755 ?
O1 Cu1 N1 154.07(5) . 3_755 ?
O1 Cu1 N1 87.90(6) 3_755 3_755 ?
N3 Cu1 N1 101.79(7) . . ?
N3 Cu1 N1 77.53(7) 3_755 . ?
O1 Cu1 N1 87.90(6) . . ?
O1 Cu1 N1 154.07(5) 3_755 . ?
N1 Cu1 N1 93.28(9) 3_755 . ?
C1 N1 C4 118.0(2) . . ?
C1 N1 Cu1 131.72(16) . . ?
C4 N1 Cu1 110.15(14) . . ?
C2 N2 C3 116.4(2) . . ?
C5 N3 N4 119.62(16) . . ?
C5 N3 Cu1 121.13(14) . . ?
N4 N3 Cu1 119.25(13) . . ?
C7 N4 N3 109.76(15) . . ?
C7 O1 Cu1 107.79(13) . . ?
C14 N5 C16 127.1(6) . . ?
C14 N5 C15 119.0(7) . . ?
C16 N5 C15 113.8(6) . . ?
O3 C14 N5 138.6(9) . . ?
C14A N5A C15A 124(4) . . ?
C14A N5A C16A 130(3) . . ?
C15A N5A C16A 105(3) . . ?
O3A C14A N5A 148(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
N1 C1 C2 N2 -0.7(4) . . . . ?
N2 C3 C4 N1 -0.8(3) . . . . ?
N2 C3 C4 C5 -178.6(2) . . . 3_755 ?
O1 C7 C8 C9 12.9(3) . . . . ?
N4 C7 C8 C9 -168.0(2) . . . . ?
O1 C7 C8 C13 -164.0(2) . . . . ?
N4 C7 C8 C13 15.0(3) . . . . ?
C13 C8 C9 C10 -0.4(4) . . . . ?
C7 C8 C9 C10 -177.5(2) . . . . ?
C8 C9 C10 O2 179.6(2) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
O2 C10 C11 C12 -179.0(3) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C10 C11 C12 C13 -0.7(5) . . . . ?
C11 C12 C13 C8 0.4(4) . . . . ?
C9 C8 C13 C12 0.2(4) . . . . ?
C7 C8 C13 C12 177.2(2) . . . . ?
C2 C1 N1 C4 0.0(4) . . . . ?
C2 C1 N1 Cu1 -175.95(19) . . . . ?
C3 C4 N1 C1 0.7(3) . . . . ?
C5 C4 N1 C1 178.6(2) 3_755 . . . ?
C3 C4 N1 Cu1 177.50(16) . . . . ?
C5 C4 N1 Cu1 -4.6(2) 3_755 . . . ?
C1 C2 N2 C3 0.6(4) . . . . ?
C4 C3 N2 C2 0.1(4) . . . . ?
C4 C5 N3 N4 -173.60(16) 3_755 . . . ?
C6 C5 N3 N4 5.6(3) . . . . ?
C4 C5 N3 Cu1 6.1(2) 3_755 . . . ?
C6 C5 N3 Cu1 -174.76(16) . . . . ?
O1 C7 N4 N3 6.9(3) . . . . ?
C8 C7 N4 N3 -172.01(16) . . . . ?
C5 N3 N4 C7 179.06(17) . . . . ?
Cu1 N3 N4 C7 -0.6(2) . . . . ?
N4 C7 O1 Cu1 -8.8(2) . . . . ?
C8 C7 O1 Cu1 170.07(14) . . . . ?
C16 N5 C14 O3 -174.2(10) . . . . ?
C15 N5 C14 O3 11.0(14) . . . . ?
C15A N5A C14A O3A 179(5) . . . . ?
C16A N5A C14A O3A -1(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
C2 H2 O2 0.93 2.42 3.307(4) 160.4 1_545 yes
C3 H3 O1 0.93 2.40 3.295(3) 160.9 8_855 yes

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_cu24
_audit_block_doi                 10.5517/ccdc.csd.cc21zwyw
_database_code_depnum_ccdc_archive 'CCDC 1906529'
loop_
_audit_author_name
_audit_author_address
'Cu four hydroxy aroylhydrazone'
;Guangdong Institute of Microbiology
China
;
_audit_update_record             
;
2019-11-25 deposited with the CCDC.	2019-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H22 Cu N8 O4, 2(C3 H7 N O)'
_chemical_formula_sum            'C32 H36 Cu N10 O6'
_chemical_formula_weight         720.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   11.7231(3)
_cell_length_b                   9.5146(3)
_cell_length_c                   30.8378(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3439.67(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2378
_cell_measurement_theta_min      4.7420
_cell_measurement_theta_max      62.6660

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             1500
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    1.387
_shelx_estimated_absorpt_T_min   0.544
_shelx_estimated_absorpt_T_max   0.607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.71820
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_reflns_number            6590
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         4.738
_diffrn_reflns_theta_max         62.705
_diffrn_reflns_theta_full        62.705
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2732
_reflns_number_gt                2223
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (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)+(0.0638P)²+1.8272P] 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         2732
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1266
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.000000 0.08905(6) 0.750000 0.0424(2) Uani 1 2 d S T P . .
N3 N 0.16172(17) 0.0867(2) 0.73526(7) 0.0405(5) Uani 1 1 d . . . . .
N4 N 0.19978(17) 0.1667(2) 0.70138(7) 0.0446(5) Uani 1 1 d . . . . .
C4 C -0.1813(2) -0.0788(3) 0.70966(8) 0.0420(6) Uani 1 1 d . . . . .
O1 O 0.00925(13) 0.2327(2) 0.69703(6) 0.0492(5) Uani 1 1 d . . . . .
N1 N -0.06751(18) -0.0708(2) 0.70594(8) 0.0504(6) Uani 1 1 d . . . . .
C5 C 0.2334(2) 0.0120(3) 0.75743(8) 0.0415(6) Uani 1 1 d . . . . .
C7 C 0.1111(2) 0.2330(3) 0.68287(8) 0.0432(6) Uani 1 1 d . . . . .
C9 C 0.2378(3) 0.2886(3) 0.61990(9) 0.0565(7) Uani 1 1 d . . . . .
H9 H 0.291614 0.225646 0.630507 0.068 Uiso 1 1 calc R U . . .
C3 C -0.2413(3) -0.1732(3) 0.68381(10) 0.0563(7) Uani 1 1 d . . . . .
H3 H -0.320095 -0.179355 0.686862 0.068 Uiso 1 1 calc R U . . .
O2 O 0.2055(3) 0.5239(3) 0.52826(8) 0.1039(10) Uani 1 1 d . . . . .
H2 H 0.152795 0.576482 0.521706 0.156 Uiso 1 1 calc R U . . .
C8 C 0.1367(2) 0.3105(3) 0.64252(8) 0.0468(6) Uani 1 1 d . . . . .
C13 C 0.0580(3) 0.4037(3) 0.62525(10) 0.0592(8) Uani 1 1 d . . . . .
H13 H -0.010600 0.418240 0.639745 0.071 Uiso 1 1 calc R U . . .
C12 C 0.0785(3) 0.4755(4) 0.58716(10) 0.0696(9) Uani 1 1 d . . . . .
H12 H 0.024328 0.537386 0.576136 0.084 Uiso 1 1 calc R U . . .
C10 C 0.2585(3) 0.3603(4) 0.58166(10) 0.0720(9) Uani 1 1 d . . . . .
H10 H 0.325967 0.344850 0.566553 0.086 Uiso 1 1 calc R U . . .
C2 C -0.0769(4) -0.2423(4) 0.65197(12) 0.0804(11) Uani 1 1 d . . . . .
H2A H -0.038052 -0.297031 0.631823 0.097 Uiso 1 1 calc R U . . .
N2 N -0.1897(3) -0.2548(3) 0.65496(9) 0.0753(8) Uani 1 1 d . . . . .
N5 N 0.0838(3) 0.8397(4) 0.45110(10) 0.0855(9) Uani 1 1 d . . . . .
C11 C 0.1792(4) 0.4547(4) 0.56583(10) 0.0710(10) Uani 1 1 d . . . . .
C1 C -0.0165(3) -0.1520(4) 0.67742(11) 0.0658(9) Uani 1 1 d . . . . .
H1 H 0.062376 -0.147699 0.674551 0.079 Uiso 1 1 calc R U . . .
C6 C 0.3589(2) 0.0168(3) 0.74974(10) 0.0539(7) Uani 1 1 d . . . . .
H6A H 0.374829 -0.010619 0.720393 0.081 Uiso 1 1 calc R U . . .
H6B H 0.396490 -0.046510 0.769321 0.081 Uiso 1 1 calc R U . . .
H6C H 0.386257 0.110631 0.754539 0.081 Uiso 1 1 calc R U . . .
O3 O 0.0351(3) 0.7113(4) 0.50973(10) 0.1205(12) Uani 1 1 d . . . . .
C15 C 0.1983(5) 0.7844(7) 0.45188(17) 0.137(2) Uani 1 1 d . . . . .
H15A H 0.206048 0.720124 0.475706 0.205 Uiso 1 1 calc R U . . .
H15B H 0.251587 0.860179 0.455278 0.205 Uiso 1 1 calc R U . . .
H15C H 0.213475 0.735966 0.425184 0.205 Uiso 1 1 calc R U . . .
C14 C 0.0573(6) 0.9354(5) 0.41687(16) 0.136(2) Uani 1 1 d . . . . .
H14A H -0.022559 0.957387 0.417608 0.204 Uiso 1 1 calc R U . . .
H14B H 0.075890 0.893070 0.389504 0.204 Uiso 1 1 calc R U . . .
H14C H 0.100900 1.020006 0.420489 0.204 Uiso 1 1 calc R U . . .
C16 C 0.0119(4) 0.7961(6) 0.48050(16) 0.1024(14) Uani 1 1 d . . . . .
H16 H -0.062104 0.831218 0.479435 0.123 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 N3 1.950(2) 3_556 ?
Cu1 N3 1.950(2) . ?
Cu1 O1 2.1326(19) . ?
Cu1 O1 2.1326(19) 3_556 ?
Cu1 N1 2.188(2) 3_556 ?
Cu1 N1 2.188(2) . ?
N3 C5 1.296(3) . ?
N3 N4 1.368(3) . ?
N4 C7 1.344(3) . ?
C4 N1 1.341(3) . ?
C4 C3 1.392(4) . ?
C4 C5 1.466(4) 3_556 ?
O1 C7 1.271(3) . ?
N1 C1 1.314(4) . ?
C5 C6 1.491(3) . ?
C7 C8 1.478(4) . ?
C9 C10 1.384(4) . ?
C9 C8 1.391(4) . ?
C9 H9 0.9300 . ?
C3 N2 1.326(4) . ?
C3 H3 0.9300 . ?
O2 C11 1.368(4) . ?
O2 H2 0.8200 . ?
C8 C13 1.386(4) . ?
C13 C12 1.380(4) . ?
C13 H13 0.9300 . ?
C12 C11 1.367(5) . ?
C12 H12 0.9300 . ?
C10 C11 1.381(5) . ?
C10 H10 0.9300 . ?
C2 N2 1.331(5) . ?
C2 C1 1.362(5) . ?
C2 H2A 0.9300 . ?
N5 C16 1.305(6) . ?
N5 C14 1.428(5) . ?
N5 C15 1.442(6) . ?
C1 H1 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
O3 C16 1.240(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16 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
N3 Cu1 N3 178.66(13) 3_556 . ?
N3 Cu1 O1 103.62(8) 3_556 . ?
N3 Cu1 O1 77.27(8) . . ?
N3 Cu1 O1 77.27(8) 3_556 3_556 ?
N3 Cu1 O1 103.62(8) . 3_556 ?
O1 Cu1 O1 100.28(11) . 3_556 ?
N3 Cu1 N1 101.48(9) 3_556 3_556 ?
N3 Cu1 N1 77.57(8) . 3_556 ?
O1 Cu1 N1 154.54(7) . 3_556 ?
O1 Cu1 N1 89.33(8) 3_556 3_556 ?
N3 Cu1 N1 77.57(9) 3_556 . ?
N3 Cu1 N1 101.47(8) . . ?
O1 Cu1 N1 89.33(8) . . ?
O1 Cu1 N1 154.54(7) 3_556 . ?
N1 Cu1 N1 91.90(13) 3_556 . ?
C5 N3 N4 119.8(2) . . ?
C5 N3 Cu1 120.96(18) . . ?
N4 N3 Cu1 119.26(16) . . ?
C7 N4 N3 109.5(2) . . ?
N1 C4 C3 119.4(3) . . ?
N1 C4 C5 116.1(2) . 3_556 ?
C3 C4 C5 124.5(2) . 3_556 ?
C7 O1 Cu1 108.19(16) . . ?
C1 N1 C4 118.4(3) . . ?
C1 N1 Cu1 131.3(2) . . ?
C4 N1 Cu1 110.26(18) . . ?
N3 C5 C4 114.7(2) . 3_556 ?
N3 C5 C6 122.7(2) . . ?
C4 C5 C6 122.6(2) 3_556 . ?
O1 C7 N4 125.4(2) . . ?
O1 C7 C8 118.8(2) . . ?
N4 C7 C8 115.8(2) . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
N2 C3 C4 122.1(3) . . ?
N2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C11 O2 H2 109.5 . . ?
C13 C8 C9 118.1(3) . . ?
C13 C8 C7 120.5(2) . . ?
C9 C8 C7 121.4(3) . . ?
C12 C13 C8 121.9(3) . . ?
C12 C13 H13 119.1 . . ?
C8 C13 H13 119.1 . . ?
C11 C12 C13 119.2(3) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
N2 C2 C1 122.2(3) . . ?
N2 C2 H2A 118.9 . . ?
C1 C2 H2A 118.9 . . ?
C3 N2 C2 116.6(3) . . ?
C16 N5 C14 125.1(5) . . ?
C16 N5 C15 118.3(4) . . ?
C14 N5 C15 116.6(5) . . ?
C12 C11 O2 122.1(4) . . ?
C12 C11 C10 120.4(3) . . ?
O2 C11 C10 117.5(3) . . ?
N1 C1 C2 121.3(3) . . ?
N1 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N5 C15 H15A 109.5 . . ?
N5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N5 C14 H14A 109.5 . . ?
N5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C16 N5 124.7(5) . . ?
O3 C16 H16 117.6 . . ?
N5 C16 H16 117.6 . . ?

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
C5 N3 N4 C7 179.1(2) . . . . ?
Cu1 N3 N4 C7 -1.8(3) . . . . ?
C3 C4 N1 C1 0.8(4) . . . . ?
C5 C4 N1 C1 178.8(3) 3_556 . . . ?
C3 C4 N1 Cu1 179.1(2) . . . . ?
C5 C4 N1 Cu1 -2.9(3) 3_556 . . . ?
N4 N3 C5 C4 -174.8(2) . . . 3_556 ?
Cu1 N3 C5 C4 6.1(3) . . . 3_556 ?
N4 N3 C5 C6 4.6(4) . . . . ?
Cu1 N3 C5 C6 -174.5(2) . . . . ?
Cu1 O1 C7 N4 -7.1(3) . . . . ?
Cu1 O1 C7 C8 172.30(18) . . . . ?
N3 N4 C7 O1 6.3(4) . . . . ?
N3 N4 C7 C8 -173.1(2) . . . . ?
N1 C4 C3 N2 -1.0(4) . . . . ?
C5 C4 C3 N2 -178.9(3) 3_556 . . . ?
C10 C9 C8 C13 1.0(4) . . . . ?
C10 C9 C8 C7 178.5(3) . . . . ?
O1 C7 C8 C13 12.8(4) . . . . ?
N4 C7 C8 C13 -167.7(3) . . . . ?
O1 C7 C8 C9 -164.6(3) . . . . ?
N4 C7 C8 C9 14.8(4) . . . . ?
C9 C8 C13 C12 -1.1(4) . . . . ?
C7 C8 C13 C12 -178.7(3) . . . . ?
C8 C13 C12 C11 -0.1(5) . . . . ?
C8 C9 C10 C11 0.4(5) . . . . ?
C4 C3 N2 C2 0.2(5) . . . . ?
C1 C2 N2 C3 0.8(6) . . . . ?
C13 C12 C11 O2 -179.1(3) . . . . ?
C13 C12 C11 C10 1.5(5) . . . . ?
C9 C10 C11 C12 -1.7(5) . . . . ?
C9 C10 C11 O2 178.9(3) . . . . ?
C4 N1 C1 C2 0.2(5) . . . . ?
Cu1 N1 C1 C2 -177.7(3) . . . . ?
N2 C2 C1 N1 -1.0(6) . . . . ?
C14 N5 C16 O3 178.8(4) . . . . ?
C15 N5 C16 O3 1.0(7) . . . . ?

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
C3 H3 O1 0.93 2.39 3.291(4) 163.0 8 yes
O2 H2 O3 0.82 1.92 2.738(5) 175.0 . yes

_refine_diff_density_max         0.454
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.048

