# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_155tup
_database_code_depnum_ccdc_archive 'CCDC 2224387'
loop_
_audit_author_name
_audit_author_address
'Vladimir Lazarenko'
;NRC Kurchatov institute
Russia
;
_audit_update_record             
;
2023-07-12 deposited with the CCDC.	2023-07-19 downloaded from the CCDC.
;
_audit_creation_date             2022-11-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 Cu N8 O5'
_chemical_formula_sum            'C23 H18 Cu N8 O5'
_chemical_formula_weight         549.99
_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 0.0026 0.0018 '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 0.2447 1.3792 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0049 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0092 0.0067 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.598(2)
_cell_length_b                   9.0780(18)
_cell_length_c                   23.574(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.20(3)
_cell_angle_gamma                90
_cell_volume                     2232.2(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1690
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.015
_cell_measurement_theta_min      2.987
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.801
_exptl_absorpt_coefficient_mu    1.164
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.811
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1124
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            16712
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        26.551
_diffrn_reflns_theta_max         31.015
_diffrn_reflns_theta_min         2.987
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.745
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5292
_reflns_number_total             6131
_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       'marccd software'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.841
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         6131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0538P)²+1.0968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1063
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
 C19(H19), C20(H20), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C16(H16A,H16B,H16C)
;
_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 0.58652(2) 0.45686(2) 0.59130(2) 0.02759(8) Uani 1 1 d . . . . .
O1 O 0.54757(13) 0.85714(13) 0.52013(5) 0.0306(3) Uani 1 1 d . . . . .
O2 O 1.03447(14) 0.44093(14) 0.66071(6) 0.0335(3) Uani 1 1 d . . . . .
O3 O 0.45180(15) 0.71063(17) 0.67573(8) 0.0471(4) Uani 1 1 d . . . . .
O4 O 0.59878(13) 0.54076(12) 0.68575(5) 0.0294(3) Uani 1 1 d . . . . .
O5 O 0.64323(15) 0.76034(15) 0.72000(7) 0.0415(3) Uani 1 1 d . . . . .
N1 N 0.85784(15) 0.53196(15) 0.68635(6) 0.0270(3) Uani 1 1 d . . . . .
H1 H 0.777653 0.540563 0.691090 0.032 Uiso 1 1 calc R . . . .
N2 N 0.85433(17) 0.30592(16) 0.63128(7) 0.0332(3) Uani 1 1 d . . . . .
N3 N 0.72197(16) 0.30295(16) 0.62626(6) 0.0300(3) Uani 1 1 d . . . . .
N4 N 0.47687(17) 0.29471(16) 0.60377(6) 0.0307(3) Uani 1 1 d . . . . .
N5 N 0.41546(16) 0.53658(16) 0.55808(7) 0.0308(3) Uani 1 1 d . . . . .
N6 N 0.40760(17) 0.67211(17) 0.53271(7) 0.0332(3) Uani 1 1 d . . . . .
N7 N 0.63688(15) 0.64772(15) 0.56122(6) 0.0277(3) Uani 1 1 d . . . . .
N8 N 0.56319(15) 0.67376(16) 0.69405(7) 0.0289(3) Uani 1 1 d . . . . .
C1 C 0.73531(18) 0.74758(18) 0.55664(7) 0.0282(3) Uani 1 1 d . . . . .
C2 C 0.86714(19) 0.73807(19) 0.57084(8) 0.0315(4) Uani 1 1 d . . . . .
H2 H 0.907979 0.649727 0.585927 0.038 Uiso 1 1 calc R . . . .
C3 C 0.9383(2) 0.8630(2) 0.56223(8) 0.0345(4) Uani 1 1 d . . . . .
H3 H 1.029062 0.860136 0.572399 0.041 Uiso 1 1 calc R . . . .
C4 C 0.8784(2) 0.9922(2) 0.53890(8) 0.0344(4) Uani 1 1 d . . . . .
H4 H 0.929532 1.075849 0.534319 0.041 Uiso 1 1 calc R . . . .
C5 C 0.7463(2) 1.00135(19) 0.52230(8) 0.0316(4) Uani 1 1 d . . . . .
H5 H 0.705008 1.087687 0.505426 0.038 Uiso 1 1 calc R . . . .
C6 C 0.67919(18) 0.87641(18) 0.53199(7) 0.0284(3) Uani 1 1 d . . . . .
C7 C 0.52773(18) 0.71888(18) 0.53872(7) 0.0284(3) Uani 1 1 d . . . . .
C8 C 0.3150(2) 0.46079(19) 0.56406(8) 0.0322(4) Uani 1 1 d . . . . .
C9 C 0.1819(2) 0.5144(2) 0.54467(9) 0.0378(4) Uani 1 1 d . . . . .
H9A H 0.163390 0.593474 0.570297 0.057 Uiso 1 1 calc GR . . . .
H9B H 0.121597 0.433076 0.545727 0.057 Uiso 1 1 calc GR . . . .
H9C H 0.172987 0.552118 0.505207 0.057 Uiso 1 1 calc GR . . . .
C10 C 0.3502(2) 0.3172(2) 0.59203(8) 0.0328(4) Uani 1 1 d . . . . .
C11 C 0.2677(2) 0.2084(2) 0.60629(8) 0.0392(4) Uani 1 1 d . . . . .
H11 H 0.177411 0.221705 0.598839 0.047 Uiso 1 1 calc R . . . .
C12 C 0.3227(2) 0.0799(2) 0.63178(9) 0.0425(5) Uani 1 1 d . . . . .
H12 H 0.268563 0.004328 0.641716 0.051 Uiso 1 1 calc R . . . .
C13 C 0.4543(2) 0.0592(2) 0.64304(8) 0.0389(4) Uani 1 1 d . . . . .
H13 H 0.490729 -0.029529 0.659947 0.047 Uiso 1 1 calc R . . . .
C14 C 0.5317(2) 0.17315(18) 0.62872(7) 0.0326(4) Uani 1 1 d . . . . .
C15 C 0.6727(2) 0.17831(18) 0.63926(7) 0.0326(4) Uani 1 1 d . . . . .
C16 C 0.7509(2) 0.05128(19) 0.66540(8) 0.0370(4) Uani 1 1 d . . . . .
H16A H 0.836073 0.055560 0.654660 0.055 Uiso 1 1 calc GR . . . .
H16B H 0.708609 -0.040972 0.651291 0.055 Uiso 1 1 calc GR . . . .
H16C H 0.759674 0.055635 0.707450 0.055 Uiso 1 1 calc GR . . . .
C17 C 0.90596(18) 0.42052(19) 0.65847(7) 0.0290(3) Uani 1 1 d . . . . .
C18 C 1.06601(18) 0.5726(2) 0.69036(8) 0.0304(3) Uani 1 1 d . . . . .
C19 C 1.18294(19) 0.6403(2) 0.70082(9) 0.0351(4) Uani 1 1 d . . . . .
H19 H 1.256335 0.598301 0.689117 0.042 Uiso 1 1 calc R . . . .
C20 C 1.18802(19) 0.7750(2) 0.72979(8) 0.0351(4) Uani 1 1 d . . . . .
H20 H 1.267163 0.826386 0.738454 0.042 Uiso 1 1 calc R . . . .
C21 C 1.07930(19) 0.8350(2) 0.74614(8) 0.0326(4) Uani 1 1 d . . . . .
H21 H 1.086119 0.926745 0.765847 0.039 Uiso 1 1 calc R . . . .
C22 C 0.96039(18) 0.76476(18) 0.73449(7) 0.0287(3) Uani 1 1 d . . . . .
H22 H 0.886110 0.806767 0.745376 0.034 Uiso 1 1 calc R . . . .
C23 C 0.95631(17) 0.63068(18) 0.70626(7) 0.0267(3) 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 O4 2.3351(13) . ?
Cu1 N3 2.0672(16) . ?
Cu1 N4 1.9300(16) . ?
Cu1 N5 1.9801(18) . ?
Cu1 N7 1.9807(14) . ?
O1 C6 1.384(2) . ?
O1 C7 1.3580(19) . ?
O2 C17 1.366(2) . ?
O2 C18 1.395(2) . ?
O3 N8 1.230(2) . ?
O4 N8 1.2902(18) . ?
O5 N8 1.236(2) . ?
N1 H1 0.8800 . ?
N1 C17 1.354(2) . ?
N1 C23 1.393(2) . ?
N2 N3 1.387(2) . ?
N2 C17 1.292(2) . ?
N3 C15 1.305(2) . ?
N4 C10 1.337(3) . ?
N4 C14 1.334(2) . ?
N5 N6 1.364(2) . ?
N5 C8 1.296(3) . ?
N6 C7 1.326(3) . ?
N7 C1 1.401(2) . ?
N7 C7 1.349(2) . ?
C1 C2 1.380(3) . ?
C1 C6 1.392(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.396(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.399(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.379(2) . ?
C8 C9 1.486(3) . ?
C8 C10 1.478(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.399(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.392(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.398(3) . ?
C14 C15 1.471(3) . ?
C15 C16 1.489(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 C19 1.366(3) . ?
C18 C23 1.387(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.397(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.389(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.396(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.384(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
N3 Cu1 O4 85.57(6) . . ?
N4 Cu1 O4 92.11(6) . . ?
N4 Cu1 N3 79.52(7) . . ?
N4 Cu1 N5 78.76(7) . . ?
N4 Cu1 N7 158.34(7) . . ?
N5 Cu1 O4 98.65(6) . . ?
N5 Cu1 N3 158.01(6) . . ?
N5 Cu1 N7 79.90(6) . . ?
N7 Cu1 O4 94.76(5) . . ?
N7 Cu1 N3 121.46(7) . . ?
C7 O1 C6 105.05(13) . . ?
C17 O2 C18 106.52(14) . . ?
N8 O4 Cu1 118.78(10) . . ?
C17 N1 H1 125.7 . . ?
C17 N1 C23 108.67(15) . . ?
C23 N1 H1 125.7 . . ?
C17 N2 N3 113.03(15) . . ?
N2 N3 Cu1 129.89(11) . . ?
C15 N3 Cu1 113.64(14) . . ?
C15 N3 N2 115.95(16) . . ?
C10 N4 Cu1 117.48(12) . . ?
C14 N4 Cu1 118.09(14) . . ?
C14 N4 C10 124.09(17) . . ?
N6 N5 Cu1 118.92(13) . . ?
C8 N5 Cu1 118.37(13) . . ?
C8 N5 N6 122.61(17) . . ?
C7 N6 N5 105.01(15) . . ?
C1 N7 Cu1 147.71(12) . . ?
C7 N7 Cu1 107.04(12) . . ?
C7 N7 C1 104.97(14) . . ?
O3 N8 O4 119.32(16) . . ?
O3 N8 O5 122.20(16) . . ?
O5 N8 O4 118.47(16) . . ?
C2 C1 N7 132.57(16) . . ?
C2 C1 C6 119.55(16) . . ?
C6 C1 N7 107.88(16) . . ?
C1 C2 H2 121.2 . . ?
C1 C2 C3 117.60(17) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.29(19) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.70(18) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 122.3 . . ?
C6 C5 C4 115.35(17) . . ?
C6 C5 H5 122.3 . . ?
O1 C6 C1 108.60(15) . . ?
C5 C6 O1 126.97(16) . . ?
C5 C6 C1 124.43(18) . . ?
N6 C7 O1 117.52(16) . . ?
N6 C7 N7 128.99(16) . . ?
N7 C7 O1 113.49(16) . . ?
N5 C8 C9 123.09(17) . . ?
N5 C8 C10 111.68(18) . . ?
C10 C8 C9 125.23(18) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C10 C8 113.05(16) . . ?
N4 C10 C11 119.29(18) . . ?
C11 C10 C8 127.7(2) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 C10 117.7(2) . . ?
C12 C11 H11 121.2 . . ?
C11 C12 H12 119.1 . . ?
C13 C12 C11 121.78(19) . . ?
C13 C12 H12 119.1 . . ?
C12 C13 H13 121.1 . . ?
C12 C13 C14 117.86(19) . . ?
C14 C13 H13 121.1 . . ?
N4 C14 C13 119.3(2) . . ?
N4 C14 C15 113.47(16) . . ?
C13 C14 C15 127.20(18) . . ?
N3 C15 C14 115.13(16) . . ?
N3 C15 C16 123.5(2) . . ?
C14 C15 C16 121.33(17) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 O2 109.78(15) . . ?
N2 C17 O2 117.40(16) . . ?
N2 C17 N1 132.81(18) . . ?
C19 C18 O2 127.23(17) . . ?
C19 C18 C23 123.87(17) . . ?
C23 C18 O2 108.84(16) . . ?
C18 C19 H19 122.0 . . ?
C18 C19 C20 115.92(18) . . ?
C20 C19 H19 122.0 . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.13(19) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 H21 119.0 . . ?
C20 C21 C22 122.03(17) . . ?
C22 C21 H21 119.0 . . ?
C21 C22 H22 121.7 . . ?
C23 C22 C21 116.53(17) . . ?
C23 C22 H22 121.7 . . ?
C18 C23 N1 106.16(15) . . ?
C22 C23 N1 133.29(17) . . ?
C22 C23 C18 120.51(17) . . ?

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 O4 N8 O3 61.06(19) . . . . ?
Cu1 O4 N8 O5 -118.47(15) . . . . ?
Cu1 N3 C15 C14 -2.19(19) . . . . ?
Cu1 N3 C15 C16 -179.48(13) . . . . ?
Cu1 N4 C10 C8 7.20(19) . . . . ?
Cu1 N4 C10 C11 -173.12(13) . . . . ?
Cu1 N4 C14 C13 174.25(13) . . . . ?
Cu1 N4 C14 C15 -4.39(19) . . . . ?
Cu1 N5 N6 C7 -1.21(19) . . . . ?
Cu1 N5 C8 C9 175.49(14) . . . . ?
Cu1 N5 C8 C10 -4.6(2) . . . . ?
Cu1 N7 C1 C2 9.5(4) . . . . ?
Cu1 N7 C1 C6 -171.38(17) . . . . ?
Cu1 N7 C7 O1 175.42(11) . . . . ?
Cu1 N7 C7 N6 -4.6(2) . . . . ?
O2 C18 C19 C20 177.64(17) . . . . ?
O2 C18 C23 N1 0.51(18) . . . . ?
O2 C18 C23 C22 -177.52(15) . . . . ?
N2 N3 C15 C14 -174.76(14) . . . . ?
N2 N3 C15 C16 8.0(2) . . . . ?
N3 N2 C17 O2 -173.71(14) . . . . ?
N3 N2 C17 N1 5.5(3) . . . . ?
N4 C10 C11 C12 -0.7(3) . . . . ?
N4 C14 C15 N3 4.2(2) . . . . ?
N4 C14 C15 C16 -178.41(15) . . . . ?
N5 N6 C7 O1 -176.01(14) . . . . ?
N5 N6 C7 N7 4.0(3) . . . . ?
N5 C8 C10 N4 -1.6(2) . . . . ?
N5 C8 C10 C11 178.76(18) . . . . ?
N6 N5 C8 C9 -0.8(3) . . . . ?
N6 N5 C8 C10 179.10(15) . . . . ?
N7 C1 C2 C3 -177.76(18) . . . . ?
N7 C1 C6 O1 -1.16(19) . . . . ?
N7 C1 C6 C5 178.03(16) . . . . ?
C1 N7 C7 O1 -0.25(19) . . . . ?
C1 N7 C7 N6 179.74(18) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C2 C1 C6 O1 178.11(15) . . . . ?
C2 C1 C6 C5 -2.7(3) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C3 C4 C5 C6 1.8(3) . . . . ?
C4 C5 C6 O1 179.17(16) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C6 O1 C7 N6 179.56(16) . . . . ?
C6 O1 C7 N7 -0.45(19) . . . . ?
C6 C1 C2 C3 3.2(3) . . . . ?
C7 O1 C6 C1 0.98(18) . . . . ?
C7 O1 C6 C5 -178.18(17) . . . . ?
C7 N7 C1 C2 -178.29(19) . . . . ?
C7 N7 C1 C6 0.85(18) . . . . ?
C8 N5 N6 C7 175.09(17) . . . . ?
C8 C10 C11 C12 178.97(18) . . . . ?
C9 C8 C10 N4 178.33(17) . . . . ?
C9 C8 C10 C11 -1.3(3) . . . . ?
C10 N4 C14 C13 1.2(3) . . . . ?
C10 N4 C14 C15 -177.42(16) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C12 C13 C14 N4 -1.6(3) . . . . ?
C12 C13 C14 C15 176.82(18) . . . . ?
C13 C14 C15 N3 -174.26(17) . . . . ?
C13 C14 C15 C16 3.1(3) . . . . ?
C14 N4 C10 C8 -179.73(15) . . . . ?
C14 N4 C10 C11 0.0(3) . . . . ?
C17 O2 C18 C19 -177.01(18) . . . . ?
C17 O2 C18 C23 0.41(19) . . . . ?
C17 N1 C23 C18 -1.26(18) . . . . ?
C17 N1 C23 C22 176.41(18) . . . . ?
C17 N2 N3 Cu1 56.1(2) . . . . ?
C17 N2 N3 C15 -132.83(17) . . . . ?
C18 O2 C17 N1 -1.22(18) . . . . ?
C18 O2 C17 N2 178.17(15) . . . . ?
C18 C19 C20 C21 -0.5(3) . . . . ?
C19 C18 C23 N1 178.04(17) . . . . ?
C19 C18 C23 C22 0.0(3) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C20 C21 C22 C23 0.7(3) . . . . ?
C21 C22 C23 N1 -178.05(17) . . . . ?
C21 C22 C23 C18 -0.6(2) . . . . ?
C23 N1 C17 O2 1.57(19) . . . . ?
C23 N1 C17 N2 -177.69(18) . . . . ?
C23 C18 C19 C20 0.6(3) . . . . ?

_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_164tup
_database_code_depnum_ccdc_archive 'CCDC 2224391'
loop_
_audit_author_name
_audit_author_address
'Vladimir Lazarenko'
;NRC Kurchatov institute
Russia
;
_audit_update_record             
;
2023-07-12 deposited with the CCDC.	2023-07-19 downloaded from the CCDC.
;
_audit_creation_date             2022-11-24
_audit_creation_method           
;
Olex2 1.2
(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         'C23 H18 Br Cu N7 O2'
_chemical_formula_sum            'C23 H18 Br Cu N7 O2'
_chemical_formula_weight         567.89
_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 0.0026 0.0018 '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'
Br Br -0.5891 2.6662 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.2447 1.3792 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0049 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0092 0.0067 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.401(2)
_cell_length_b                   8.6870(17)
_cell_length_c                   24.368(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.27(3)
_cell_angle_gamma                90
_cell_volume                     2184.0(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2776
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.104
_cell_measurement_theta_min      1.766
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.738
_exptl_absorpt_coefficient_mu    3.227
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'XDS, Kabsh 2010'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'brownish green'
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1140
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.005
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_av_unetI/netI     0.1045
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            14706
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        26.551
_diffrn_reflns_theta_max         31.104
_diffrn_reflns_theta_min         1.766
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.745
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3695
_reflns_number_total             5913
_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       'marccd software'
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.811
_refine_diff_density_min         -1.186
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5913
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0560
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0510P)²+2.2911P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1534
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C11(H11), C22(H22), C2(H2), C21(H21), C12(H12), C5(H5), C20(H20),
 C4(H4), C13(H13), C19(H19), C3(H3)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_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
Br1 Br 0.44459(4) 0.38146(6) 0.30951(2) 0.03154(14) Uani 1 1 d . . . . .
Cu1 Cu 0.42871(5) 0.54912(7) 0.40199(3) 0.03020(16) Uani 1 1 d . . . . .
O1 O -0.0276(3) 0.5957(4) 0.34206(16) 0.0340(8) Uani 1 1 d . . . . .
O2 O 0.4532(3) 0.1452(4) 0.47962(15) 0.0333(8) Uani 1 1 d . . . . .
N4 N 0.5430(4) 0.7206(5) 0.39100(17) 0.0308(9) Uani 1 1 d . . . . .
N1 N 0.1450(4) 0.4855(5) 0.31317(18) 0.0321(9) Uani 1 1 d . . . . .
H1 H 0.225019 0.470602 0.306118 0.039 Uiso 1 1 calc R . . . .
N3 N 0.2966(4) 0.7163(5) 0.37007(18) 0.0325(9) Uani 1 1 d . . . . .
N6 N 0.5990(4) 0.3341(5) 0.46487(18) 0.0335(9) Uani 1 1 d . . . . .
N5 N 0.5975(4) 0.4726(5) 0.43952(18) 0.0317(9) Uani 1 1 d . . . . .
N7 N 0.3695(4) 0.3645(5) 0.44018(17) 0.0314(9) Uani 1 1 d . . . . .
N2 N 0.1616(4) 0.7216(5) 0.36706(18) 0.0331(9) Uani 1 1 d . . . . .
C14 C 0.6707(5) 0.6987(6) 0.4062(2) 0.0312(10) Uani 1 1 d . . . . .
C7 C 0.1046(4) 0.6060(6) 0.3418(2) 0.0317(10) Uani 1 1 d . . . . .
C10 C 0.4932(5) 0.8489(6) 0.3677(2) 0.0324(11) Uani 1 1 d . . . . .
C11 C 0.5737(5) 0.9690(6) 0.3561(2) 0.0356(11) Uani 1 1 d . . . . .
H11 H 0.539421 1.062092 0.339821 0.043 Uiso 1 1 calc R . . . .
C17 C 0.4764(5) 0.2888(6) 0.4611(2) 0.0303(10) Uani 1 1 d . . . . .
C22 C 0.1358(5) 0.2710(7) 0.4281(2) 0.0332(11) Uani 1 1 d . . . . .
H22 H 0.096741 0.362898 0.412853 0.040 Uiso 1 1 calc R . . . .
C8 C 0.3484(5) 0.8440(6) 0.3566(2) 0.0298(10) Uani 1 1 d . . . . .
C2 C 0.0294(5) 0.2517(7) 0.2696(2) 0.0348(11) Uani 1 1 d . . . . .
H2 H 0.102222 0.202339 0.257401 0.042 Uiso 1 1 calc R . . . .
C1 C 0.0404(4) 0.3888(6) 0.2966(2) 0.0290(10) Uani 1 1 d . . . . .
C6 C -0.0663(5) 0.4607(6) 0.3143(2) 0.0321(10) Uani 1 1 d . . . . .
C15 C 0.7008(5) 0.5513(6) 0.4345(2) 0.0321(10) Uani 1 1 d . . . . .
C16 C 0.8329(5) 0.4969(7) 0.4559(2) 0.0369(12) Uani 1 1 d . . . . .
H16A H 0.833878 0.460676 0.494014 0.055 Uiso 1 1 calc GR . . . .
H16B H 0.894695 0.581809 0.455048 0.055 Uiso 1 1 calc GR . . . .
H16C H 0.857451 0.412311 0.432708 0.055 Uiso 1 1 calc GR . . . .
C18 C 0.3194(4) 0.1264(6) 0.4673(2) 0.0316(10) Uani 1 1 d . . . . .
C9 C 0.2730(5) 0.9773(6) 0.3325(2) 0.0327(11) Uani 1 1 d . . . . .
H9A H 0.229568 0.949945 0.295767 0.049 Uiso 1 1 calc GR . . . .
H9B H 0.331388 1.064453 0.329343 0.049 Uiso 1 1 calc GR . . . .
H9C H 0.207932 1.005852 0.356500 0.049 Uiso 1 1 calc GR . . . .
C23 C 0.2681(5) 0.2607(6) 0.4433(2) 0.0316(10) Uani 1 1 d . . . . .
C21 C 0.0621(5) 0.1412(7) 0.4362(2) 0.0376(12) Uani 1 1 d . . . . .
H21 H -0.029026 0.144907 0.425860 0.045 Uiso 1 1 calc R . . . .
C12 C 0.7061(5) 0.9478(7) 0.3693(2) 0.0377(12) Uani 1 1 d . . . . .
H12 H 0.763732 1.026917 0.361146 0.045 Uiso 1 1 calc R . . . .
C5 C -0.1896(5) 0.3998(7) 0.3062(2) 0.0357(12) Uani 1 1 d . . . . .
H5 H -0.261514 0.450193 0.318702 0.043 Uiso 1 1 calc R . . . .
C20 C 0.1177(5) 0.0059(7) 0.4588(2) 0.0373(12) Uani 1 1 d . . . . .
H20 H 0.064337 -0.081262 0.462465 0.045 Uiso 1 1 calc R . . . .
C4 C -0.2016(5) 0.2604(7) 0.2786(2) 0.0365(11) Uani 1 1 d . . . . .
H4 H -0.284638 0.213630 0.271695 0.044 Uiso 1 1 calc R . . . .
C13 C 0.7557(5) 0.8143(7) 0.3941(2) 0.0351(11) Uani 1 1 d . . . . .
H13 H 0.846652 0.801138 0.402852 0.042 Uiso 1 1 calc R . . . .
C19 C 0.2491(5) -0.0037(7) 0.4761(2) 0.0351(11) Uani 1 1 d . . . . .
H19 H 0.288276 -0.093705 0.492946 0.042 Uiso 1 1 calc R . . . .
C3 C -0.0956(5) 0.1864(7) 0.2607(2) 0.0379(12) Uani 1 1 d . . . . .
H3 H -0.107747 0.090349 0.242137 0.046 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Cu1 2.7056(9) . ?
Cu1 N4 1.946(4) . ?
Cu1 N3 2.081(4) . ?
Cu1 N5 1.989(4) . ?
Cu1 N7 1.991(4) . ?
O1 C7 1.379(5) . ?
O1 C6 1.387(6) . ?
O2 C17 1.359(6) . ?
O2 C18 1.395(6) . ?
N4 C14 1.346(6) . ?
N4 C10 1.326(7) . ?
N1 H1 0.8800 . ?
N1 C7 1.354(7) . ?
N1 C1 1.394(6) . ?
N3 N2 1.398(5) . ?
N3 C8 1.294(7) . ?
N6 N5 1.352(6) . ?
N6 C17 1.326(6) . ?
N5 C15 1.292(6) . ?
N7 C17 1.336(6) . ?
N7 C23 1.397(6) . ?
N2 C7 1.282(7) . ?
C14 C15 1.469(8) . ?
C14 C13 1.394(7) . ?
C10 C11 1.389(7) . ?
C10 C8 1.496(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(7) . ?
C22 H22 0.9500 . ?
C22 C23 1.382(7) . ?
C22 C21 1.391(8) . ?
C8 C9 1.478(7) . ?
C2 H2 0.9500 . ?
C2 C1 1.358(7) . ?
C2 C3 1.410(7) . ?
C1 C6 1.389(6) . ?
C6 C5 1.378(7) . ?
C15 C16 1.484(7) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 C23 1.382(7) . ?
C18 C19 1.377(7) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C20 1.393(8) . ?
C12 H12 0.9500 . ?
C12 C13 1.377(8) . ?
C5 H5 0.9500 . ?
C5 C4 1.383(8) . ?
C20 H20 0.9500 . ?
C20 C19 1.381(8) . ?
C4 H4 0.9500 . ?
C4 C3 1.393(7) . ?
C13 H13 0.9500 . ?
C19 H19 0.9500 . ?
C3 H3 0.9500 . ?

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
N4 Cu1 Br1 101.24(13) . . ?
N4 Cu1 N3 78.48(17) . . ?
N4 Cu1 N5 78.45(18) . . ?
N4 Cu1 N7 155.77(18) . . ?
N3 Cu1 Br1 99.87(13) . . ?
N5 Cu1 Br1 93.42(13) . . ?
N5 Cu1 N3 155.20(18) . . ?
N5 Cu1 N7 79.82(17) . . ?
N7 Cu1 Br1 90.62(13) . . ?
N7 Cu1 N3 120.54(16) . . ?
C7 O1 C6 106.3(4) . . ?
C17 O2 C18 104.5(4) . . ?
C14 N4 Cu1 116.9(4) . . ?
C10 N4 Cu1 119.3(3) . . ?
C10 N4 C14 123.7(4) . . ?
C7 N1 H1 125.3 . . ?
C7 N1 C1 109.5(4) . . ?
C1 N1 H1 125.3 . . ?
N2 N3 Cu1 130.8(3) . . ?
C8 N3 Cu1 114.6(3) . . ?
C8 N3 N2 114.0(4) . . ?
C17 N6 N5 106.1(4) . . ?
N6 N5 Cu1 117.8(3) . . ?
C15 N5 Cu1 118.4(4) . . ?
C15 N5 N6 123.6(4) . . ?
C17 N7 Cu1 106.4(3) . . ?
C17 N7 C23 105.0(4) . . ?
C23 N7 Cu1 145.7(4) . . ?
C7 N2 N3 113.5(4) . . ?
N4 C14 C15 113.4(4) . . ?
N4 C14 C13 118.0(5) . . ?
C13 C14 C15 128.6(5) . . ?
N1 C7 O1 109.1(4) . . ?
N2 C7 O1 116.7(4) . . ?
N2 C7 N1 134.3(4) . . ?
N4 C10 C11 120.3(5) . . ?
N4 C10 C8 112.5(4) . . ?
C11 C10 C8 127.1(5) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 C10 117.4(5) . . ?
C12 C11 H11 121.3 . . ?
N6 C17 O2 117.3(4) . . ?
N6 C17 N7 128.8(5) . . ?
N7 C17 O2 113.8(4) . . ?
C23 C22 H22 121.4 . . ?
C23 C22 C21 117.2(5) . . ?
C21 C22 H22 121.4 . . ?
N3 C8 C10 114.9(4) . . ?
N3 C8 C9 123.7(5) . . ?
C9 C8 C10 121.4(4) . . ?
C1 C2 H2 121.7 . . ?
C1 C2 C3 116.5(5) . . ?
C3 C2 H2 121.7 . . ?
C2 C1 N1 133.1(4) . . ?
C2 C1 C6 121.6(5) . . ?
C6 C1 N1 105.3(5) . . ?
O1 C6 C1 109.7(4) . . ?
C5 C6 O1 127.0(5) . . ?
C5 C6 C1 123.2(5) . . ?
N5 C15 C14 112.0(4) . . ?
N5 C15 C16 122.8(5) . . ?
C14 C15 C16 125.1(5) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C23 C18 O2 108.2(4) . . ?
C19 C18 O2 126.7(5) . . ?
C19 C18 C23 125.1(5) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C22 C23 N7 132.6(5) . . ?
C22 C23 C18 119.1(5) . . ?
C18 C23 N7 108.3(4) . . ?
C22 C21 H21 119.0 . . ?
C22 C21 C20 122.1(5) . . ?
C20 C21 H21 119.0 . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.3(5) . . ?
C13 C12 H12 119.3 . . ?
C6 C5 H5 122.2 . . ?
C6 C5 C4 115.6(5) . . ?
C4 C5 H5 122.2 . . ?
C21 C20 H20 119.4 . . ?
C19 C20 C21 121.2(5) . . ?
C19 C20 H20 119.4 . . ?
C5 C4 H4 119.0 . . ?
C5 C4 C3 122.0(5) . . ?
C3 C4 H4 119.0 . . ?
C14 C13 H13 120.4 . . ?
C12 C13 C14 119.1(5) . . ?
C12 C13 H13 120.4 . . ?
C18 C19 C20 115.3(5) . . ?
C18 C19 H19 122.4 . . ?
C20 C19 H19 122.4 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.1(5) . . ?
C4 C3 H3 119.4 . . ?

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 N4 C14 C15 -6.2(6) . . . . ?
Cu1 N4 C14 C13 174.2(4) . . . . ?
Cu1 N4 C10 C11 -175.8(4) . . . . ?
Cu1 N4 C10 C8 4.2(6) . . . . ?
Cu1 N3 N2 C7 -56.3(6) . . . . ?
Cu1 N3 C8 C10 -1.3(6) . . . . ?
Cu1 N3 C8 C9 179.2(4) . . . . ?
Cu1 N5 C15 C14 7.1(6) . . . . ?
Cu1 N5 C15 C16 -173.6(4) . . . . ?
Cu1 N7 C17 O2 -168.3(3) . . . . ?
Cu1 N7 C17 N6 10.1(7) . . . . ?
Cu1 N7 C23 C22 -23.8(10) . . . . ?
Cu1 N7 C23 C18 157.1(5) . . . . ?
O1 C6 C5 C4 -177.9(5) . . . . ?
O2 C18 C23 N7 0.2(6) . . . . ?
O2 C18 C23 C22 -179.0(4) . . . . ?
O2 C18 C19 C20 -178.2(5) . . . . ?
N4 C14 C15 N5 -0.6(6) . . . . ?
N4 C14 C15 C16 -179.8(5) . . . . ?
N4 C14 C13 C12 2.5(8) . . . . ?
N4 C10 C11 C12 0.7(8) . . . . ?
N4 C10 C8 N3 -1.7(6) . . . . ?
N4 C10 C8 C9 177.9(4) . . . . ?
N1 C1 C6 O1 -1.3(6) . . . . ?
N1 C1 C6 C5 -179.3(5) . . . . ?
N3 N2 C7 O1 173.7(4) . . . . ?
N3 N2 C7 N1 -6.7(9) . . . . ?
N6 N5 C15 C14 -178.9(4) . . . . ?
N6 N5 C15 C16 0.4(8) . . . . ?
N5 N6 C17 O2 174.5(4) . . . . ?
N5 N6 C17 N7 -3.9(7) . . . . ?
N2 N3 C8 C10 171.2(4) . . . . ?
N2 N3 C8 C9 -8.4(7) . . . . ?
C14 N4 C10 C11 1.8(8) . . . . ?
C14 N4 C10 C8 -178.3(4) . . . . ?
C7 O1 C6 C1 -0.5(5) . . . . ?
C7 O1 C6 C5 177.3(5) . . . . ?
C7 N1 C1 C2 -176.5(5) . . . . ?
C7 N1 C1 C6 2.8(6) . . . . ?
C10 N4 C14 C15 176.2(5) . . . . ?
C10 N4 C14 C13 -3.4(7) . . . . ?
C10 C11 C12 C13 -1.5(8) . . . . ?
C11 C10 C8 N3 178.3(5) . . . . ?
C11 C10 C8 C9 -2.1(8) . . . . ?
C11 C12 C13 C14 -0.2(8) . . . . ?
C17 O2 C18 C23 -1.4(5) . . . . ?
C17 O2 C18 C19 177.2(5) . . . . ?
C17 N6 N5 Cu1 -5.0(5) . . . . ?
C17 N6 N5 C15 -179.1(5) . . . . ?
C17 N7 C23 C22 -179.8(5) . . . . ?
C17 N7 C23 C18 1.1(6) . . . . ?
C22 C21 C20 C19 2.1(8) . . . . ?
C8 N3 N2 C7 132.8(5) . . . . ?
C8 C10 C11 C12 -179.2(5) . . . . ?
C2 C1 C6 O1 178.1(5) . . . . ?
C2 C1 C6 C5 0.1(8) . . . . ?
C1 N1 C7 O1 -3.2(6) . . . . ?
C1 N1 C7 N2 177.2(6) . . . . ?
C1 C2 C3 C4 0.3(8) . . . . ?
C1 C6 C5 C4 -0.3(8) . . . . ?
C6 O1 C7 N1 2.3(5) . . . . ?
C6 O1 C7 N2 -178.0(5) . . . . ?
C6 C5 C4 C3 0.5(8) . . . . ?
C15 C14 C13 C12 -177.0(5) . . . . ?
C18 O2 C17 N6 -176.3(5) . . . . ?
C18 O2 C17 N7 2.3(5) . . . . ?
C23 N7 C17 O2 -2.2(6) . . . . ?
C23 N7 C17 N6 176.2(5) . . . . ?
C23 C22 C21 C20 0.4(8) . . . . ?
C23 C18 C19 C20 0.2(8) . . . . ?
C21 C22 C23 N7 178.5(5) . . . . ?
C21 C22 C23 C18 -2.5(7) . . . . ?
C21 C20 C19 C18 -2.4(8) . . . . ?
C5 C4 C3 C2 -0.5(9) . . . . ?
C13 C14 C15 N5 178.9(5) . . . . ?
C13 C14 C15 C16 -0.3(9) . . . . ?
C19 C18 C23 N7 -178.5(5) . . . . ?
C19 C18 C23 C22 2.3(8) . . . . ?
C3 C2 C1 N1 179.1(5) . . . . ?
C3 C2 C1 C6 -0.1(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_163tup
# Added during the CSD deposition process: Tuesday 18 July 2023 10:18 AM
# end Validation Reply Form

_database_code_depnum_ccdc_archive 'CCDC 2224388'
loop_
_audit_author_name
_audit_author_address
'Vladimir Lazarenko'
;NRC Kurchatov institute
Russia
;
_audit_update_record             
;
2023-07-18 deposited with the CCDC.	2023-07-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT601_163tup              
;
PROBLEM: Unit Cell Contains Solvent Accessible VOIDS of .        213 Ang**3
RESPONSE: a careful study of the problem showed that the structure has a channel containing an insignificant amount of residual electron density per volume, which indeed indicates a high porosity of the structure, as well as its organization by multiple intermolecular interactions between the molecules of the main substance
;
_vrf_PLAT029_163tup              
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.954 Why?
RESPONSE: due to the low reflectivity of the crystal and the triclinic syngony, the combination of three sets of diffraction data in different random orientations did not give a great completeness of the final data
;
_audit_creation_date             2023-07-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 Cu N7 O3, Cl O4'
_chemical_formula_sum            'C23 H20 Cl Cu N7 O7'
_chemical_formula_weight         605.45
_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 0.0026 0.0018 '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'
Cl Cl 0.1436 0.1747 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.2447 1.3792 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0049 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0092 0.0067 '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                   7.2800(15)
_cell_length_b                   13.060(3)
_cell_length_c                   14.970(3)
_cell_angle_alpha                80.19(3)
_cell_angle_beta                 83.70(3)
_cell_angle_gamma                73.99(3)
_cell_volume                     1345.1(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3445
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.747
_cell_measurement_theta_min      2.406
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.899
_exptl_absorpt_coefficient_mu    1.088
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'XDS, Kabsh 2010'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             618
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0905
_diffrn_reflns_av_unetI/netI     0.0812
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18104
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        26.551
_diffrn_reflns_theta_max         27.747
_diffrn_reflns_theta_min         2.406
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.745
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4091
_reflns_number_total             5252
_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       'marccd software'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.721
_refine_diff_density_min         -1.390
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0528
_refine_ls_restrained_S_all      0.989
_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)+(0.0902P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1441
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Rotating group:
 O3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C12(H12), C11(H11), C19(H19), C20(H20), C13(H13), C22(H22), C5(H5),
 C4(H4), C21(H21), C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.78607(5) 0.55486(3) 0.61089(3) 0.02391(14) Uani 1 1 d . . . . .
Cl1 Cl 0.36782(11) 0.88275(6) 0.69108(6) 0.0284(2) Uani 1 1 d . . . . .
O3 O 0.4672(3) 0.60848(17) 0.65831(17) 0.0273(5) Uani 1 1 d . . . . .
H3A H 0.398926 0.578220 0.630402 0.041 Uiso 1 1 d R U . . .
H3B H 0.420016 0.678500 0.640571 0.041 Uiso 1 1 d R U . . .
O1 O 0.8189(3) 0.41994(18) 0.92177(17) 0.0289(5) Uani 1 1 d . . . . .
O2 O 0.7111(3) 0.30007(17) 0.52067(17) 0.0281(5) Uani 1 1 d . . . . .
O7 O 0.3709(4) 0.83276(19) 0.61150(19) 0.0399(6) Uani 1 1 d . . . . .
O5 O 0.1773(3) 0.9455(2) 0.7106(2) 0.0397(6) Uani 1 1 d . . . . .
N3 N 0.8646(4) 0.5986(2) 0.7233(2) 0.0263(6) Uani 1 1 d . . . . .
N5 N 0.7550(4) 0.5593(2) 0.4806(2) 0.0262(6) Uani 1 1 d . . . . .
N7 N 0.7837(4) 0.4029(2) 0.6112(2) 0.0250(6) Uani 1 1 d . . . . .
O6 O 0.4280(5) 0.7991(2) 0.7655(2) 0.0483(7) Uani 1 1 d . . . . .
N1 N 0.5968(4) 0.5054(2) 0.8250(2) 0.0274(6) Uani 1 1 d . . . . .
H1 H 0.539938 0.548701 0.778543 0.033 Uiso 1 1 calc R U . . .
N6 N 0.7311(4) 0.4681(2) 0.4532(2) 0.0261(6) Uani 1 1 d . . . . .
N4 N 0.8231(4) 0.6939(2) 0.5608(2) 0.0255(6) Uani 1 1 d . . . . .
N2 N 0.9115(4) 0.5360(2) 0.8068(2) 0.0283(6) Uani 1 1 d . . . . .
O4 O 0.4930(4) 0.9520(2) 0.6734(3) 0.0539(9) Uani 1 1 d . . . . .
C10 C 0.8682(4) 0.7515(2) 0.6161(2) 0.0261(7) Uani 1 1 d . . . . .
C17 C 0.7439(4) 0.3955(2) 0.5288(2) 0.0246(7) Uani 1 1 d . . . . .
C8 C 0.8996(4) 0.6931(2) 0.7088(2) 0.0264(7) Uani 1 1 d . . . . .
C15 C 0.7572(4) 0.6465(3) 0.4252(2) 0.0269(7) Uani 1 1 d . . . . .
C12 C 0.8506(4) 0.8948(3) 0.4926(3) 0.0298(7) Uani 1 1 d . . . . .
H12 H 0.857504 0.966027 0.468883 0.036 Uiso 1 1 calc R U . . .
C18 C 0.7298(4) 0.2417(3) 0.6072(2) 0.0273(7) Uani 1 1 d . . . . .
C11 C 0.8871(4) 0.8554(3) 0.5828(3) 0.0283(7) Uani 1 1 d . . . . .
H11 H 0.923394 0.897167 0.620459 0.034 Uiso 1 1 calc R U . . .
C19 C 0.7027(5) 0.1407(3) 0.6358(3) 0.0308(7) Uani 1 1 d . . . . .
H19 H 0.667874 0.101020 0.595885 0.037 Uiso 1 1 calc R U . . .
C23 C 0.7765(4) 0.3047(2) 0.6636(2) 0.0265(7) Uani 1 1 d . . . . .
C20 C 0.7295(5) 0.1007(3) 0.7267(3) 0.0365(8) Uani 1 1 d . . . . .
H20 H 0.711114 0.031669 0.750243 0.044 Uiso 1 1 calc R U . . .
C1 C 0.5141(4) 0.4384(3) 0.8899(2) 0.0280(7) Uani 1 1 d . . . . .
C13 C 0.8042(5) 0.8327(3) 0.4361(2) 0.0287(7) Uani 1 1 d . . . . .
H13 H 0.779889 0.860480 0.374384 0.034 Uiso 1 1 calc R U . . .
C7 C 0.7781(5) 0.4928(2) 0.8452(2) 0.0264(7) Uani 1 1 d . . . . .
C6 C 0.6526(5) 0.3855(3) 0.9494(2) 0.0281(7) Uani 1 1 d . . . . .
C22 C 0.8099(5) 0.2621(3) 0.7538(3) 0.0312(7) Uani 1 1 d . . . . .
H22 H 0.849246 0.300980 0.793001 0.037 Uiso 1 1 calc R U . . .
C16 C 0.7365(5) 0.6601(3) 0.3256(3) 0.0305(7) Uani 1 1 d . . . . .
H16A H 0.849965 0.614453 0.296883 0.046 Uiso 1 1 calc R U . . .
H16B H 0.723556 0.735581 0.299477 0.046 Uiso 1 1 calc R U . . .
H16C H 0.622314 0.639063 0.315057 0.046 Uiso 1 1 calc R U . . .
C14 C 0.7943(4) 0.7295(3) 0.4721(2) 0.0258(7) Uani 1 1 d . . . . .
C5 C 0.6268(5) 0.3116(3) 1.0230(3) 0.0343(8) Uani 1 1 d . . . . .
H5 H 0.724786 0.276139 1.063168 0.041 Uiso 1 1 calc R U . . .
C4 C 0.4447(5) 0.2921(3) 1.0347(3) 0.0376(8) Uani 1 1 d . . . . .
H4 H 0.417682 0.241587 1.084640 0.045 Uiso 1 1 calc R U . . .
C21 C 0.7829(5) 0.1592(3) 0.7843(3) 0.0355(8) Uani 1 1 d . . . . .
H21 H 0.801507 0.128664 0.846031 0.043 Uiso 1 1 calc R U . . .
C9 C 0.9661(5) 0.7399(3) 0.7789(3) 0.0350(8) Uani 1 1 d . . . . .
H9A H 0.948614 0.698515 0.838773 0.052 Uiso 1 1 calc R U . . .
H9B H 0.891504 0.814923 0.778666 0.052 Uiso 1 1 calc R U . . .
H9C H 1.102005 0.737248 0.765456 0.052 Uiso 1 1 calc R U . . .
C3 C 0.3038(5) 0.3444(3) 0.9755(3) 0.0366(8) Uani 1 1 d . . . . .
H3 H 0.182813 0.328542 0.985861 0.044 Uiso 1 1 calc R U . . .
C2 C 0.3334(5) 0.4201(3) 0.9009(3) 0.0321(7) Uani 1 1 d . . . . .
H2 H 0.236357 0.456404 0.860411 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 O3 2.301(2) . ?
Cu1 N3 2.050(3) . ?
Cu1 N5 1.977(3) . ?
Cu1 N7 1.988(3) . ?
Cu1 N4 1.922(3) . ?
Cl1 O7 1.448(3) . ?
Cl1 O5 1.430(3) . ?
Cl1 O6 1.433(3) . ?
Cl1 O4 1.428(3) . ?
O3 H3A 0.8877 . ?
O3 H3B 0.8881 . ?
O1 C7 1.363(4) . ?
O1 C6 1.403(4) . ?
O2 C17 1.359(4) . ?
O2 C18 1.387(4) . ?
N3 N2 1.393(4) . ?
N3 C8 1.306(4) . ?
N5 N6 1.384(4) . ?
N5 C15 1.292(4) . ?
N7 C17 1.322(5) . ?
N7 C23 1.396(4) . ?
N1 H1 0.8800 . ?
N1 C1 1.395(4) . ?
N1 C7 1.346(4) . ?
N6 C17 1.341(4) . ?
N4 C10 1.329(5) . ?
N4 C14 1.349(4) . ?
N2 C7 1.288(4) . ?
C10 C8 1.473(5) . ?
C10 C11 1.403(4) . ?
C8 C9 1.485(5) . ?
C15 C16 1.489(5) . ?
C15 C14 1.486(5) . ?
C12 H12 0.9500 . ?
C12 C11 1.387(5) . ?
C12 C13 1.392(5) . ?
C18 C19 1.376(5) . ?
C18 C23 1.400(5) . ?
C11 H11 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.386(6) . ?
C23 C22 1.391(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.394(6) . ?
C1 C6 1.375(5) . ?
C1 C2 1.388(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.381(5) . ?
C6 C5 1.368(5) . ?
C22 H22 0.9500 . ?
C22 C21 1.404(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C5 H5 0.9500 . ?
C5 C4 1.405(5) . ?
C4 H4 0.9500 . ?
C4 C3 1.382(5) . ?
C21 H21 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C3 H3 0.9500 . ?
C3 C2 1.400(5) . ?
C2 H2 0.9500 . ?

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 O3 91.24(10) . . ?
N5 Cu1 O3 98.17(10) . . ?
N5 Cu1 N3 157.36(11) . . ?
N5 Cu1 N7 80.24(12) . . ?
N7 Cu1 O3 94.03(10) . . ?
N7 Cu1 N3 119.76(12) . . ?
N4 Cu1 O3 98.52(10) . . ?
N4 Cu1 N3 79.63(12) . . ?
N4 Cu1 N5 78.65(12) . . ?
N4 Cu1 N7 156.74(13) . . ?
O5 Cl1 O7 109.05(18) . . ?
O5 Cl1 O6 110.40(18) . . ?
O6 Cl1 O7 108.13(16) . . ?
O4 Cl1 O7 109.4(2) . . ?
O4 Cl1 O5 108.93(16) . . ?
O4 Cl1 O6 110.9(2) . . ?
Cu1 O3 H3A 110.3 . . ?
Cu1 O3 H3B 110.6 . . ?
H3A O3 H3B 103.5 . . ?
C7 O1 C6 106.1(2) . . ?
C17 O2 C18 104.4(3) . . ?
N2 N3 Cu1 128.7(2) . . ?
C8 N3 Cu1 113.9(2) . . ?
C8 N3 N2 116.6(3) . . ?
N6 N5 Cu1 117.9(2) . . ?
C15 N5 Cu1 119.1(2) . . ?
C15 N5 N6 123.0(3) . . ?
C17 N7 Cu1 107.0(2) . . ?
C17 N7 C23 105.2(3) . . ?
C23 N7 Cu1 146.6(2) . . ?
C1 N1 H1 125.7 . . ?
C7 N1 H1 125.7 . . ?
C7 N1 C1 108.7(3) . . ?
C17 N6 N5 104.8(3) . . ?
C10 N4 Cu1 118.3(2) . . ?
C10 N4 C14 123.5(3) . . ?
C14 N4 Cu1 118.1(2) . . ?
C7 N2 N3 113.0(3) . . ?
N4 C10 C8 113.1(3) . . ?
N4 C10 C11 119.8(3) . . ?
C11 C10 C8 127.1(3) . . ?
N7 C17 O2 114.5(3) . . ?
N7 C17 N6 129.4(3) . . ?
N6 C17 O2 116.0(3) . . ?
N3 C8 C10 114.8(3) . . ?
N3 C8 C9 123.6(3) . . ?
C10 C8 C9 121.5(3) . . ?
N5 C15 C16 124.4(3) . . ?
N5 C15 C14 111.5(3) . . ?
C14 C15 C16 124.0(3) . . ?
C11 C12 H12 119.2 . . ?
C11 C12 C13 121.6(3) . . ?
C13 C12 H12 119.2 . . ?
O2 C18 C23 108.1(3) . . ?
C19 C18 O2 127.4(3) . . ?
C19 C18 C23 124.5(3) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 C10 117.4(3) . . ?
C12 C11 H11 121.3 . . ?
C18 C19 H19 122.1 . . ?
C18 C19 C20 115.7(3) . . ?
C20 C19 H19 122.1 . . ?
N7 C23 C18 107.7(3) . . ?
C22 C23 N7 133.1(3) . . ?
C22 C23 C18 119.2(3) . . ?
C19 C20 H20 119.2 . . ?
C19 C20 C21 121.6(3) . . ?
C21 C20 H20 119.2 . . ?
C6 C1 N1 106.2(3) . . ?
C6 C1 C2 121.4(3) . . ?
C2 C1 N1 132.3(3) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 C12 118.2(3) . . ?
C14 C13 H13 120.9 . . ?
N1 C7 O1 110.1(3) . . ?
N2 C7 O1 117.5(3) . . ?
N2 C7 N1 132.5(3) . . ?
C1 C6 O1 108.9(3) . . ?
C5 C6 O1 127.0(3) . . ?
C5 C6 C1 124.1(3) . . ?
C23 C22 H22 121.5 . . ?
C23 C22 C21 117.0(3) . . ?
C21 C22 H22 121.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N4 C14 C15 112.2(3) . . ?
N4 C14 C13 119.4(3) . . ?
C13 C14 C15 128.4(3) . . ?
C6 C5 H5 122.5 . . ?
C6 C5 C4 115.1(3) . . ?
C4 C5 H5 122.5 . . ?
C5 C4 H4 119.2 . . ?
C3 C4 C5 121.7(3) . . ?
C3 C4 H4 119.2 . . ?
C20 C21 C22 121.8(4) . . ?
C20 C21 H21 119.1 . . ?
C22 C21 H21 119.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C3 H3 118.9 . . ?
C4 C3 C2 122.2(3) . . ?
C2 C3 H3 118.9 . . ?
C1 C2 C3 115.6(3) . . ?
C1 C2 H2 122.2 . . ?
C3 C2 H2 122.2 . . ?

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 N3 N2 C7 -56.5(4) . . . . ?
Cu1 N3 C8 C10 2.5(3) . . . . ?
Cu1 N3 C8 C9 -177.5(3) . . . . ?
Cu1 N5 N6 C17 -2.3(3) . . . . ?
Cu1 N5 C15 C16 179.6(2) . . . . ?
Cu1 N5 C15 C14 3.0(3) . . . . ?
Cu1 N7 C17 O2 -171.48(19) . . . . ?
Cu1 N7 C17 N6 8.3(4) . . . . ?
Cu1 N7 C23 C18 164.3(3) . . . . ?
Cu1 N7 C23 C22 -17.5(6) . . . . ?
Cu1 N4 C10 C8 5.1(3) . . . . ?
Cu1 N4 C10 C11 -176.9(2) . . . . ?
Cu1 N4 C14 C15 -6.2(3) . . . . ?
Cu1 N4 C14 C13 174.6(2) . . . . ?
O1 C6 C5 C4 -180.0(3) . . . . ?
O2 C18 C19 C20 -179.6(3) . . . . ?
O2 C18 C23 N7 0.8(3) . . . . ?
O2 C18 C23 C22 -177.7(3) . . . . ?
N3 N2 C7 O1 172.4(3) . . . . ?
N3 N2 C7 N1 -8.0(5) . . . . ?
N5 N6 C17 O2 175.4(2) . . . . ?
N5 N6 C17 N7 -4.4(4) . . . . ?
N5 C15 C14 N4 1.9(4) . . . . ?
N5 C15 C14 C13 -178.9(3) . . . . ?
N7 C23 C22 C21 178.2(3) . . . . ?
N1 C1 C6 O1 0.4(4) . . . . ?
N1 C1 C6 C5 -179.7(3) . . . . ?
N1 C1 C2 C3 179.4(4) . . . . ?
N6 N5 C15 C16 -0.6(5) . . . . ?
N6 N5 C15 C14 -177.3(3) . . . . ?
N4 C10 C8 N3 -4.9(4) . . . . ?
N4 C10 C8 C9 175.1(3) . . . . ?
N4 C10 C11 C12 2.1(4) . . . . ?
N2 N3 C8 C10 173.5(2) . . . . ?
N2 N3 C8 C9 -6.5(5) . . . . ?
C10 N4 C14 C15 176.6(3) . . . . ?
C10 N4 C14 C13 -2.6(4) . . . . ?
C17 O2 C18 C19 177.3(3) . . . . ?
C17 O2 C18 C23 -0.9(3) . . . . ?
C17 N7 C23 C18 -0.3(3) . . . . ?
C17 N7 C23 C22 177.9(3) . . . . ?
C8 N3 N2 C7 134.1(3) . . . . ?
C8 C10 C11 C12 179.9(3) . . . . ?
C15 N5 N6 C17 177.9(3) . . . . ?
C12 C13 C14 N4 2.3(5) . . . . ?
C12 C13 C14 C15 -176.8(3) . . . . ?
C18 O2 C17 N7 0.8(3) . . . . ?
C18 O2 C17 N6 -179.1(2) . . . . ?
C18 C19 C20 C21 -0.8(5) . . . . ?
C18 C23 C22 C21 -3.8(5) . . . . ?
C11 C10 C8 N3 177.3(3) . . . . ?
C11 C10 C8 C9 -2.7(5) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
C19 C18 C23 N7 -177.5(3) . . . . ?
C19 C18 C23 C22 4.0(5) . . . . ?
C19 C20 C21 C22 0.8(6) . . . . ?
C23 N7 C17 O2 -0.3(3) . . . . ?
C23 N7 C17 N6 179.5(3) . . . . ?
C23 C18 C19 C20 -1.6(5) . . . . ?
C23 C22 C21 C20 1.5(5) . . . . ?
C1 N1 C7 O1 -0.3(4) . . . . ?
C1 N1 C7 N2 -179.9(4) . . . . ?
C1 C6 C5 C4 0.1(6) . . . . ?
C13 C12 C11 C10 -2.4(5) . . . . ?
C7 O1 C6 C1 -0.5(4) . . . . ?
C7 O1 C6 C5 179.5(4) . . . . ?
C7 N1 C1 C6 0.0(4) . . . . ?
C7 N1 C1 C2 -179.8(4) . . . . ?
C6 O1 C7 N1 0.5(4) . . . . ?
C6 O1 C7 N2 -179.8(3) . . . . ?
C6 C1 C2 C3 -0.3(5) . . . . ?
C6 C5 C4 C3 0.0(6) . . . . ?
C16 C15 C14 N4 -174.7(3) . . . . ?
C16 C15 C14 C13 4.4(5) . . . . ?
C14 N4 C10 C8 -177.7(3) . . . . ?
C14 N4 C10 C11 0.3(5) . . . . ?
C5 C4 C3 C2 -0.3(6) . . . . ?
C4 C3 C2 C1 0.4(6) . . . . ?
C2 C1 C6 O1 -179.9(3) . . . . ?
C2 C1 C6 C5 0.1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
