# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2144718'
loop_
_audit_author_name
_audit_author_address
'Anna Vologzhanina'
;INEOS RAS
Russia
;
_audit_update_record             
;
2022-01-26 deposited with the CCDC.	2022-03-04 downloaded from the CCDC.
;
_audit_creation_date             2020-06-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '0.5(C32 H36 Cu6 N16 O24)'
_chemical_formula_sum            'C16 H18 Cu3 N8 O12'
_chemical_formula_weight         705.00
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.396(3)
_cell_length_b                   17.171(7)
_cell_length_c                   9.335(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.808(10)
_cell_angle_gamma                90
_cell_volume                     1181.5(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    794
_cell_measurement_temperature    120
_cell_measurement_theta_max      20.72
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   0.652
_shelx_estimated_absorpt_T_min   0.534
_exptl_absorpt_coefficient_mu    2.756
_exptl_absorpt_correction_T_max  0.3426
_exptl_absorpt_correction_T_min  0.2377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1000 before and 0.0790 after correction.
The Ratio of minimum to maximum transmission is 0.6938.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.982
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             706
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1735
_diffrn_reflns_av_unetI/netI     0.1967
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17003
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.286
_diffrn_reflns_theta_min         2.372
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker D8 Quest PHOTON detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2213
_reflns_number_total             5160
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.177
_refine_diff_density_min         -1.484
_refine_diff_density_rms         0.222
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         5160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2003
_refine_ls_R_factor_gt           0.0715
_refine_ls_restrained_S_all      0.990
_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)+(0.0060P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1479
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.0000 0.5000 0.5000 0.0131(2) Uani 1 2 d S T P . .
Cu2 Cu 0.84889(9) 0.65696(3) 0.62221(7) 0.01336(15) Uani 1 1 d . . . . .
O1 O 1.1705(5) 0.42401(18) 0.5870(4) 0.0148(7) Uani 1 1 d . . . . .
O2 O 1.0203(5) 0.24760(18) 0.9444(4) 0.0153(8) Uani 1 1 d . . . . .
O3 O 0.6285(5) 0.71643(19) 0.5858(4) 0.0170(8) Uani 1 1 d . . . . .
O4 O 0.0723(5) 0.60385(19) 0.6895(4) 0.0183(8) Uani 1 1 d . . . . .
O5 O 0.8108(5) 0.46529(19) 0.6195(4) 0.0164(8) Uani 1 1 d . . . . .
O6 O 0.7236(5) 0.57594(19) 0.7208(4) 0.0163(8) Uani 1 1 d . . . . .
N1 N 1.1334(6) 0.3953(2) 0.7168(5) 0.0169(9) Uani 1 1 d . . . . .
N2 N 1.0651(6) 0.3147(2) 0.8791(5) 0.0153(9) Uani 1 1 d . . . . .
N3 N 0.4835(6) 0.6966(2) 0.6574(5) 0.0159(9) Uani 1 1 d . . . . .
N4 N 0.2311(6) 0.6449(2) 0.7037(5) 0.0157(9) Uani 1 1 d . . . . .
C1 C 1.0848(7) 0.3213(3) 0.7392(6) 0.0145(10) Uani 1 1 d . . . . .
H1 H 1.0677 0.2814 0.6689 0.017 Uiso 1 1 calc R . . . .
C2 C 1.1443(7) 0.4351(3) 0.8442(6) 0.0181(11) Uani 1 1 d . . . . .
H2 H 1.1757 0.4884 0.8580 0.022 Uiso 1 1 calc R . . . .
C3 C 1.1018(8) 0.3839(3) 0.9471(6) 0.0190(12) Uani 1 1 d . . . . .
H3 H 1.0983 0.3943 1.0468 0.023 Uiso 1 1 calc R . . . .
C4 C 0.3472(7) 0.6512(3) 0.6019(6) 0.0151(10) Uani 1 1 d . . . . .
H4 H 0.3356 0.6282 0.5090 0.018 Uiso 1 1 calc R . . . .
C5 C 0.4523(8) 0.7189(3) 0.7919(6) 0.0218(12) Uani 1 1 d . . . . .
H5 H 0.5278 0.7515 0.8536 0.026 Uiso 1 1 calc R . . . .
C6 C 0.2919(8) 0.6859(3) 0.8228(6) 0.0233(12) Uani 1 1 d . . . . .
H6 H 0.2347 0.6906 0.9097 0.028 Uiso 1 1 calc R . . . .
C7 C 0.7219(7) 0.5038(3) 0.7039(6) 0.0145(10) Uani 1 1 d . . . . .
C8 C 0.5990(8) 0.4569(3) 0.7919(7) 0.0299(15) Uani 1 1 d . . . . .
H8A H 0.4849 0.4460 0.7343 0.045 Uiso 1 1 calc GR . . . .
H8B H 0.5738 0.4865 0.8778 0.045 Uiso 1 1 calc GR . . . .
H8C H 0.6585 0.4077 0.8209 0.045 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.944(3) 3_766 ?
Cu1 O1 1.944(3) . ?
Cu1 O5 1.955(4) . ?
Cu1 O5 1.955(4) 3_766 ?
Cu2 O1 2.392(4) 3_766 ?
Cu2 O2 1.961(3) 2_756 ?
Cu2 O3 1.929(4) . ?
Cu2 O4 1.945(3) 1_655 ?
Cu2 O6 1.945(3) . ?
O1 Cu2 2.392(4) 3_766 ?
O1 N1 1.358(5) . ?
O2 Cu2 1.961(3) 2_746 ?
O2 N2 1.357(5) . ?
O3 N3 1.355(5) . ?
O4 Cu2 1.945(3) 1_455 ?
O4 N4 1.366(5) . ?
O5 C7 1.256(6) . ?
O6 C7 1.249(6) . ?
N1 C1 1.342(6) . ?
N1 C2 1.368(6) . ?
N2 C1 1.330(6) . ?
N2 C3 1.364(6) . ?
N3 C4 1.344(6) . ?
N3 C5 1.350(7) . ?
N4 C4 1.338(7) . ?
N4 C6 1.360(7) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C2 C3 1.358(7) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.367(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.509(7) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.00(14) 3_766 . ?
O1 Cu1 O5 91.57(14) . . ?
O1 Cu1 O5 91.56(14) 3_766 3_766 ?
O1 Cu1 O5 88.43(14) 3_766 . ?
O1 Cu1 O5 88.44(14) . 3_766 ?
O5 Cu1 O5 180.0 . 3_766 ?
O2 Cu2 O1 101.53(13) 2_756 3_766 ?
O3 Cu2 O1 99.89(14) . 3_766 ?
O3 Cu2 O2 87.47(15) . 2_756 ?
O3 Cu2 O4 170.92(16) . 1_655 ?
O3 Cu2 O6 91.91(15) . . ?
O4 Cu2 O1 88.99(14) 1_655 3_766 ?
O4 Cu2 O2 92.66(15) 1_655 2_756 ?
O4 Cu2 O6 86.39(15) 1_655 . ?
O6 Cu2 O1 88.42(14) . 3_766 ?
O6 Cu2 O2 170.00(15) . 2_756 ?
Cu1 O1 Cu2 93.25(14) . 3_766 ?
N1 O1 Cu1 116.4(3) . . ?
N1 O1 Cu2 121.0(3) . 3_766 ?
N2 O2 Cu2 112.7(3) . 2_746 ?
N3 O3 Cu2 118.2(3) . . ?
N4 O4 Cu2 119.3(3) . 1_455 ?
C7 O5 Cu1 129.4(3) . . ?
C7 O6 Cu2 130.5(3) . . ?
O1 N1 C2 126.4(4) . . ?
C1 N1 O1 124.1(4) . . ?
C1 N1 C2 109.6(4) . . ?
O2 N2 C3 125.2(4) . . ?
C1 N2 O2 124.3(4) . . ?
C1 N2 C3 110.4(4) . . ?
C4 N3 O3 123.7(4) . . ?
C4 N3 C5 110.0(4) . . ?
C5 N3 O3 126.3(4) . . ?
C4 N4 O4 124.8(4) . . ?
C4 N4 C6 110.5(4) . . ?
C6 N4 O4 124.7(5) . . ?
N1 C1 H1 126.7 . . ?
N2 C1 N1 106.6(4) . . ?
N2 C1 H1 126.7 . . ?
N1 C2 H2 126.5 . . ?
C3 C2 N1 106.9(4) . . ?
C3 C2 H2 126.5 . . ?
N2 C3 H3 126.8 . . ?
C2 C3 N2 106.4(5) . . ?
C2 C3 H3 126.8 . . ?
N3 C4 H4 126.9 . . ?
N4 C4 N3 106.2(4) . . ?
N4 C4 H4 126.9 . . ?
N3 C5 H5 126.4 . . ?
N3 C5 C6 107.3(5) . . ?
C6 C5 H5 126.4 . . ?
N4 C6 C5 106.0(5) . . ?
N4 C6 H6 127.0 . . ?
C5 C6 H6 127.0 . . ?
O5 C7 C8 115.6(4) . . ?
O6 C7 O5 127.0(5) . . ?
O6 C7 C8 117.5(5) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2144719'
loop_
_audit_author_name
_audit_author_address
'Anna Vologzhanina'
;INEOS RAS
Russia
;
_audit_update_record             
;
2022-01-26 deposited with the CCDC.	2022-03-04 downloaded from the CCDC.
;
_audit_creation_date             2022-01-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C5 H8 Cu N2 O5, H2 O'
_chemical_formula_sum            'C5 H10 Cu N2 O6'
_chemical_formula_weight         257.69
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.6088(19)
_cell_length_b                   9.929(2)
_cell_length_c                   9.850(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.297(7)
_cell_angle_gamma                90
_cell_volume                     939.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9009
_cell_measurement_temperature    295
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      2.93
_shelx_estimated_absorpt_T_max   0.873
_shelx_estimated_absorpt_T_min   0.479
_exptl_absorpt_coefficient_mu    2.332
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1288 before and 0.0581 after correction.
The Ratio of minimum to maximum transmission is 0.7475.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.822
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18004
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.542
_diffrn_reflns_theta_min         2.929
_diffrn_ambient_temperature      295
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Quest PHOTON detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2577
_reflns_number_total             2867
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.189
_refine_diff_density_min         -0.968
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2867
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²+1.8829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1031
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uiso(N1A) = Uiso(N2A) = Uiso(N2) = Uiso(N1)
Uiso(C5A) = Uiso(C5)
2. Others
 Fixed Sof: N1(0.5) N2(0.5) C2(0.5) C3(0.5) H3(0.5) C4(0.5) H4(0.5) C5(0.5)
 H5C(0.5) H5D(0.5) H5E(0.5) N1A(0.5) N2A(0.5) C2A(0.5) C3A(0.5) H3A(0.5)
 C4A(0.5) H4A(0.5) C5A(0.5) H5AA(0.5) H5AB(0.5) H5AC(0.5)
3.a Riding coordinates:
 O5(H5A,H5B), O6(H6A,H6B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C3A(H3A), C4A(H4A)
3.c Idealised Me refined as rotating group:
 C5(H5C,H5D,H5E), C5A(H5AA,H5AB,H5AC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.44500(3) 0.40076(3) 0.61448(3) 0.01982(10) Uani 1 1 d . . . . .
O1 O 0.4530(2) 0.2058(2) 0.6294(2) 0.0333(4) Uani 1 1 d . . . . .
O2 O 0.2727(3) 0.1940(3) 0.4846(3) 0.0523(6) Uani 1 1 d . . . . .
O3 O 0.3058(2) 0.43856(19) 0.7435(2) 0.0309(4) Uani 1 1 d . . . . .
O4 O 0.06047(19) 0.08902(16) 0.95020(18) 0.0241(4) Uani 1 1 d . . . . .
O5 O 0.6316(3) 0.4384(3) 0.7646(3) 0.0563(7) Uani 1 1 d . . . . .
H5A H 0.6697 0.3830 0.8250 0.084 Uiso 1 1 d R . . . .
H5B H 0.6836 0.5009 0.7336 0.084 Uiso 1 1 d R . . . .
C1 C 0.3630(4) 0.1433(3) 0.5577(3) 0.0361(6) Uani 1 1 d . . . . .
H1 H 0.3658 0.0497 0.5609 0.043 Uiso 1 1 calc R . . . .
N1 N 0.2743(4) 0.3359(4) 0.8278(4) 0.0212(4) Uiso 0.5 1 d . . P A 1
N2 N 0.1658(4) 0.1780(4) 0.9267(4) 0.0212(4) Uiso 0.5 1 d . . P A 1
C2 C 0.1561(5) 0.2654(4) 0.8227(4) 0.0153(7) Uiso 0.5 1 d . . P A 1
C3 C 0.2877(6) 0.1894(6) 0.9972(6) 0.0282(10) Uiso 0.5 1 d . . P A 1
H3 H 0.3182 0.1382 1.0712 0.034 Uiso 0.5 1 calc R . P A 1
C4 C 0.3576(6) 0.2944(6) 0.9345(6) 0.0276(10) Uiso 0.5 1 d . . P A 1
H4 H 0.4440 0.3296 0.9602 0.033 Uiso 0.5 1 calc R . P A 1
C5 C 0.0430(8) 0.2794(9) 0.7218(8) 0.0446(11) Uiso 0.5 1 d . . P A 1
H5C H -0.0289 0.3352 0.7580 0.067 Uiso 0.5 1 calc GR . P A 1
H5D H 0.0056 0.1922 0.7002 0.067 Uiso 0.5 1 calc GR . P A 1
H5E H 0.0780 0.3201 0.6411 0.067 Uiso 0.5 1 calc GR . P A 1
N1A N 0.2074(4) 0.3489(4) 0.7706(4) 0.0212(4) Uiso 0.5 1 d . . P A 2
N2A N 0.0904(4) 0.1927(4) 0.8615(4) 0.0212(4) Uiso 0.5 1 d . . P A 2
C2A C 0.2104(6) 0.2551(5) 0.8649(5) 0.0275(10) Uiso 0.5 1 d . . P A 2
C3A C 0.0065(8) 0.2499(8) 0.7598(8) 0.0410(14) Uiso 0.5 1 d . . P A 2
H3A H -0.0835 0.2237 0.7351 0.049 Uiso 0.5 1 calc R . P A 2
C4A C 0.0781(7) 0.3473(8) 0.7056(7) 0.0418(14) Uiso 0.5 1 d . . P A 2
H4A H 0.0478 0.4048 0.6365 0.050 Uiso 0.5 1 calc R . P A 2
C5A C 0.3270(8) 0.2262(8) 0.9609(8) 0.0446(11) Uiso 0.5 1 d . . P A 2
H5AA H 0.2926 0.2217 1.0516 0.067 Uiso 0.5 1 calc GR . P A 2
H5AB H 0.3952 0.2965 0.9557 0.067 Uiso 0.5 1 calc GR . P A 2
H5AC H 0.3687 0.1416 0.9379 0.067 Uiso 0.5 1 calc GR . P A 2
O6 O 0.6545(3) 0.0943(3) 0.8286(3) 0.0621(8) Uani 1 1 d . . . . .
H6A H 0.5997 0.1371 0.7731 0.093 Uiso 1 1 d R . . . .
H6B H 0.7007 0.1540 0.8720 0.093 Uiso 1 1 d 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
Cu1 O1 1.943(2) . ?
Cu1 O3 1.9031(19) . ?
Cu1 O4 1.9851(17) 4_665 ?
Cu1 O4 1.9752(17) 2_556 ?
Cu1 O5 2.328(3) . ?
O1 C1 1.267(4) . ?
O2 C1 1.223(4) . ?
O3 N1 1.353(4) . ?
O3 N1A 1.330(4) . ?
O4 Cu1 1.9851(17) 4_566 ?
O4 Cu1 1.9752(17) 2_546 ?
O4 N2 1.367(4) . ?
O4 N2A 1.385(4) . ?
O5 H5A 0.8836 . ?
O5 H5B 0.8581 . ?
C1 H1 0.9300 . ?
N1 C2 1.334(6) . ?
N1 C4 1.371(7) . ?
N2 C2 1.344(6) . ?
N2 C3 1.353(7) . ?
C2 C5 1.462(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(8) . ?
C4 H4 0.9300 . ?
C5 H5C 0.9600 . ?
C5 H5D 0.9600 . ?
C5 H5E 0.9600 . ?
N1A C2A 1.316(7) . ?
N1A C4A 1.385(8) . ?
N2A C2A 1.309(7) . ?
N2A C3A 1.392(8) . ?
C2A C5A 1.477(9) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.309(10) . ?
C4A H4A 0.9300 . ?
C5A H5AA 0.9600 . ?
C5A H5AB 0.9600 . ?
C5A H5AC 0.9600 . ?
O6 H6A 0.8622 . ?
O6 H6B 0.8498 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O4 165.50(8) . 2_556 ?
O1 Cu1 O4 95.21(8) . 4_665 ?
O1 Cu1 O5 94.76(10) . . ?
O3 Cu1 O1 99.97(8) . . ?
O3 Cu1 O4 161.53(8) . 4_665 ?
O3 Cu1 O4 90.85(7) . 2_556 ?
O3 Cu1 O5 94.98(11) . . ?
O4 Cu1 O4 72.54(8) 2_556 4_665 ?
O4 Cu1 O5 94.18(10) 4_665 . ?
O4 Cu1 O5 93.87(9) 2_556 . ?
C1 O1 Cu1 114.87(19) . . ?
N1 O3 Cu1 115.6(2) . . ?
N1A O3 Cu1 121.0(2) . . ?
Cu1 O4 Cu1 107.46(8) 2_546 4_566 ?
N2 O4 Cu1 122.3(2) . 4_566 ?
N2 O4 Cu1 124.9(2) . 2_546 ?
N2A O4 Cu1 120.3(2) . 2_546 ?
N2A O4 Cu1 127.2(2) . 4_566 ?
Cu1 O5 H5A 129.0 . . ?
Cu1 O5 H5B 109.7 . . ?
H5A O5 H5B 117.1 . . ?
O1 C1 H1 116.8 . . ?
O2 C1 O1 126.3(3) . . ?
O2 C1 H1 116.8 . . ?
O3 N1 C4 124.2(4) . . ?
C2 N1 O3 125.1(4) . . ?
C2 N1 C4 110.7(4) . . ?
C2 N2 O4 120.5(4) . . ?
C2 N2 C3 112.5(4) . . ?
C3 N2 O4 127.0(4) . . ?
N1 C2 N2 105.4(4) . . ?
N1 C2 C5 126.5(5) . . ?
N2 C2 C5 128.1(5) . . ?
N2 C3 H3 127.6 . . ?
N2 C3 C4 104.8(5) . . ?
C4 C3 H3 127.6 . . ?
N1 C4 C3 106.6(5) . . ?
N1 C4 H4 126.7 . . ?
C3 C4 H4 126.7 . . ?
C2 C5 H5C 109.5 . . ?
C2 C5 H5D 109.5 . . ?
C2 C5 H5E 109.5 . . ?
H5C C5 H5D 109.5 . . ?
H5C C5 H5E 109.5 . . ?
H5D C5 H5E 109.5 . . ?
O3 N1A C4A 123.3(5) . . ?
C2A N1A O3 127.7(4) . . ?
C2A N1A C4A 108.9(5) . . ?
O4 N2A C3A 129.2(5) . . ?
C2A N2A O4 122.1(4) . . ?
C2A N2A C3A 108.7(5) . . ?
N1A C2A C5A 126.4(6) . . ?
N2A C2A N1A 108.2(5) . . ?
N2A C2A C5A 125.4(6) . . ?
N2A C3A H3A 126.5 . . ?
C4A C3A N2A 107.1(6) . . ?
C4A C3A H3A 126.5 . . ?
N1A C4A H4A 126.4 . . ?
C3A C4A N1A 107.1(6) . . ?
C3A C4A H4A 126.4 . . ?
C2A C5A H5AA 109.5 . . ?
C2A C5A H5AB 109.5 . . ?
C2A C5A H5AC 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
H6A O6 H6B 106.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2144720'
loop_
_audit_author_name
_audit_author_address
'Anna Vologzhanina'
;INEOS RAS
Russia
;
_audit_update_record             
;
2022-01-26 deposited with the CCDC.	2022-03-04 downloaded from the CCDC.
;
_audit_creation_date             2020-11-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '0.5(C16 H20 Cu2 N8 O8)'
_chemical_formula_sum            'C8 H10 Cu N4 O4'
_chemical_formula_weight         289.74
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   5.868(5)
_cell_length_b                   8.771(7)
_cell_length_c                   10.174(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.18(3)
_cell_angle_gamma                90
_cell_volume                     513.7(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1332
_cell_measurement_temperature    295
_cell_measurement_theta_max      30.35
_cell_measurement_theta_min      4.08
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.136
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1104 before and 0.0564 after correction.
The Ratio of minimum to maximum transmission is 0.7784.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.873
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             294
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5125
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.475
_diffrn_reflns_theta_min         4.083
_diffrn_ambient_temperature      295
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker D8 Quest PHOTON detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1287
_reflns_number_total             1519
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     80
_refine_ls_number_reflns         1519
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0292
_refine_ls_restrained_S_all      0.995
_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)+(0.0544P)²+0.2029P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0899
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
Cu1 Cu 0.5000 0.0000 0.5000 0.01919(12) Uani 1 2 d S T P . .
O1 O 0.6054(3) 0.20583(17) 0.48242(15) 0.0364(4) Uani 1 1 d . . . . .
O2 O 0.2694(3) 0.54198(17) 0.13818(14) 0.0253(3) Uani 1 1 d . . . . .
N1 N 0.5516(3) 0.27490(19) 0.36051(17) 0.0278(4) Uani 1 1 d . . . . .
N2 N 0.3982(3) 0.42613(18) 0.20252(16) 0.0227(3) Uani 1 1 d . . . . .
C1 C 0.2210(4) 0.4377(3) 0.4091(2) 0.0345(5) Uani 1 1 d . . . . .
H1A H 0.0674 0.4008 0.3733 0.052 Uiso 1 1 calc GR . . . .
H1B H 0.2209 0.5471 0.4076 0.052 Uiso 1 1 calc GR . . . .
H1C H 0.2686 0.4027 0.4996 0.052 Uiso 1 1 calc GR . . . .
C2 C 0.3844(3) 0.3796(2) 0.32674(19) 0.0244(4) Uani 1 1 d . . . . .
C3 C 0.5739(3) 0.3489(2) 0.1568(2) 0.0288(4) Uani 1 1 d . . . . .
H3 H 0.6159 0.3599 0.0737 0.035 Uiso 1 1 calc R . . . .
C4 C 0.6721(4) 0.2542(2) 0.2571(2) 0.0316(4) Uani 1 1 d . . . . .
H4 H 0.7960 0.1882 0.2568 0.038 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
Cu1 O1 1.9279(19) . ?
Cu1 O1 1.9279(19) 3_656 ?
Cu1 O2 1.9362(19) 4_666 ?
Cu1 O2 1.9362(19) 2_545 ?
O1 N1 1.361(2) . ?
O2 Cu1 1.9362(19) 2 ?
O2 N2 1.357(2) . ?
N1 C2 1.339(3) . ?
N1 C4 1.389(3) . ?
N2 C2 1.345(3) . ?
N2 C3 1.387(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.480(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.355(3) . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 . 3_656 ?
O1 Cu1 O2 90.81(7) . 4_666 ?
O1 Cu1 O2 90.81(7) 3_656 2_545 ?
O1 Cu1 O2 89.19(7) 3_656 4_666 ?
O1 Cu1 O2 89.19(7) . 2_545 ?
O2 Cu1 O2 180.0 4_666 2_545 ?
N1 O1 Cu1 118.64(12) . . ?
N2 O2 Cu1 120.54(12) . 2 ?
O1 N1 C4 124.72(18) . . ?
C2 N1 O1 124.62(19) . . ?
C2 N1 C4 110.53(17) . . ?
O2 N2 C3 125.79(17) . . ?
C2 N2 O2 123.42(16) . . ?
C2 N2 C3 110.57(17) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C2 N2 105.93(17) . . ?
N1 C2 C1 127.8(2) . . ?
N2 C2 C1 126.22(19) . . ?
N2 C3 H3 126.8 . . ?
C4 C3 N2 106.38(19) . . ?
C4 C3 H3 126.8 . . ?
N1 C4 H4 126.7 . . ?
C3 C4 N1 106.59(18) . . ?
C3 C4 H4 126.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 2144721'
loop_
_audit_author_name
_audit_author_address
'Anna Vologzhanina'
;INEOS RAS
Russia
;
_audit_update_record             
;
2022-01-26 deposited with the CCDC.	2022-03-04 downloaded from the CCDC.
;
_audit_creation_date             2020-11-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '0.5(C20 H28 Cu2 N8 O8)'
_chemical_formula_sum            'C10 H14 Cu N4 O4'
_chemical_formula_weight         317.79
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.832(9)
_cell_length_b                   9.541(9)
_cell_length_c                   12.769(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1197.8(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    973
_cell_measurement_temperature    295
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      3.49
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.841
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1042 before and 0.0490 after correction.
The Ratio of minimum to maximum transmission is 0.8803.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14505
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.844
_diffrn_reflns_theta_min         3.376
_diffrn_ambient_temperature      295
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_device_type  'Bruker D8 Quest PHOTON detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1129
_reflns_number_total             1566
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     90
_refine_ls_number_reflns         1566
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.087
_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)+(0.0423P)²+0.8540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0933
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C)
;
_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
Cu1 Cu 0.5000 0.0000 0.5000 0.01878(14) Uani 1 2 d S T P . .
O1 O 0.53878(18) 0.19156(18) 0.54086(16) 0.0276(4) Uani 1 1 d . . . . .
O2 O 0.18029(18) 0.52171(17) 0.56076(15) 0.0271(4) Uani 1 1 d . . . . .
N1 N 0.4446(2) 0.2892(2) 0.51325(16) 0.0221(5) Uani 1 1 d . . . . .
N2 N 0.2819(2) 0.4395(2) 0.52196(16) 0.0218(4) Uani 1 1 d . . . . .
C1 C 0.3492(2) 0.3419(2) 0.5767(2) 0.0227(5) Uani 1 1 d . . . . .
H1 H 0.3326 0.3157 0.6457 0.027 Uiso 1 1 calc R . . . .
C2 C 0.3333(3) 0.4484(3) 0.4220(2) 0.0240(5) Uani 1 1 d . . . . .
C3 C 0.4376(3) 0.3527(3) 0.4161(2) 0.0244(6) Uani 1 1 d . . . . .
C4 C 0.2784(3) 0.5487(3) 0.3434(2) 0.0358(7) Uani 1 1 d . . . . .
H4A H 0.1815 0.5380 0.3389 0.054 Uiso 1 1 calc GR . . . .
H4B H 0.3185 0.5300 0.2763 0.054 Uiso 1 1 calc GR . . . .
H4C H 0.2998 0.6427 0.3645 0.054 Uiso 1 1 calc GR . . . .
C5 C 0.5322(3) 0.3152(3) 0.3295(2) 0.0367(7) Uani 1 1 d . . . . .
H5A H 0.6217 0.3494 0.3454 0.055 Uiso 1 1 calc GR . . . .
H5B H 0.5009 0.3569 0.2654 0.055 Uiso 1 1 calc GR . . . .
H5C H 0.5349 0.2152 0.3217 0.055 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.939(2) 5_656 ?
Cu1 O1 1.939(2) . ?
Cu1 O2 1.946(2) 8_655 ?
Cu1 O2 1.946(2) 4_556 ?
O1 N1 1.360(3) . ?
O2 Cu1 1.946(2) 4_456 ?
O2 N2 1.363(3) . ?
N1 C1 1.338(3) . ?
N1 C3 1.382(3) . ?
N2 C1 1.339(3) . ?
N2 C2 1.376(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(4) . ?
C2 C4 1.488(4) . ?
C3 C5 1.489(4) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 5_656 . ?
O1 Cu1 O2 91.63(8) 5_656 8_655 ?
O1 Cu1 O2 88.37(8) . 8_655 ?
O1 Cu1 O2 91.63(8) . 4_556 ?
O1 Cu1 O2 88.37(8) 5_656 4_556 ?
O2 Cu1 O2 180.0 8_655 4_556 ?
N1 O1 Cu1 116.23(15) . . ?
N2 O2 Cu1 117.49(14) . 4_456 ?
O1 N1 C3 124.5(2) . . ?
C1 N1 O1 125.3(2) . . ?
C1 N1 C3 110.1(2) . . ?
O2 N2 C2 124.8(2) . . ?
C1 N2 O2 124.9(2) . . ?
C1 N2 C2 110.3(2) . . ?
N1 C1 N2 106.9(2) . . ?
N1 C1 H1 126.5 . . ?
N2 C1 H1 126.5 . . ?
N2 C2 C4 122.1(2) . . ?
C3 C2 N2 106.5(2) . . ?
C3 C2 C4 131.4(3) . . ?
N1 C3 C5 122.0(2) . . ?
C2 C3 N1 106.2(2) . . ?
C2 C3 C5 131.7(3) . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# 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_imo2h
_database_code_depnum_ccdc_archive 'CCDC 2144717'
loop_
_audit_author_name
_audit_author_address
'Anna Vologzhanina'
;INEOS RAS
Russia
;
_audit_update_record             
;
2022-02-28 deposited with the CCDC.	2022-03-04 downloaded from the CCDC.
;
_audit_creation_date             2022-02-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C4 H6 Cu N2 O5, H O0.5'
_chemical_formula_sum            'C4 H7 Cu N2 O5.50'
_chemical_formula_weight         234.66
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   22.5046(18)
_cell_length_b                   10.0382(9)
_cell_length_c                   6.9385(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1567.4(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6885
_cell_measurement_temperature    295
_cell_measurement_theta_max      30.37
_cell_measurement_theta_min      2.72
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.781
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1454 before and 0.0495 after correction.
The Ratio of minimum to maximum transmission is 0.6743.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.989
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11277
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        28.000
_diffrn_reflns_theta_max         30.505
_diffrn_reflns_theta_min         2.719
_diffrn_ambient_temperature      295.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Bruker D8 Quest PHOTON detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2037
_reflns_number_total             2394
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.199
_refine_diff_density_min         -0.973
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.089
_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)+(0.0433P)²+5.1400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1155
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O6(H6A,H6B), O7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
;
_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 0.40411(2) 0.40888(4) 0.81846(5) 0.02165(13) Uani 1 1 d . . . . .
O1 O 0.39363(17) 0.250000 0.6539(4) 0.0275(7) Uani 1 2 d S T P . .
O2 O 0.42305(14) 0.250000 -0.0144(4) 0.0189(6) Uani 1 2 d S T P . .
O3 O 0.41263(13) 0.5169(2) 1.0453(4) 0.0377(6) Uani 1 1 d . . . . .
O4 O 0.36835(12) 0.5363(3) 0.6439(4) 0.0358(6) Uani 1 1 d . . . . .
O5 O 0.28366(14) 0.4588(4) 0.7638(6) 0.0594(9) Uani 1 1 d . . . . .
O6 O 0.49589(13) 0.4523(4) 0.7004(4) 0.0531(9) Uani 1 1 d . . . . .
H6A H 0.522916 0.478610 0.785970 0.080 Uiso 1 1 d R U . . .
H6B H 0.515786 0.380600 0.661180 0.080 Uiso 1 1 d R U . . .
N1 N 0.38220(19) 0.250000 0.4626(5) 0.0257(8) Uani 1 2 d S T P . .
N2 N 0.39518(16) 0.250000 0.1602(5) 0.0181(6) Uani 1 2 d S T P . .
N3 N 0.39199(12) 0.6434(3) 1.0492(4) 0.0237(5) Uani 1 1 d . . . . .
C1 C 0.31152(19) 0.5316(5) 0.6550(6) 0.0447(10) Uani 1 1 d . . . . .
H1 H 0.289901 0.587580 0.574512 0.054 Uiso 1 1 calc R U . . .
C2 C 0.4240(2) 0.250000 0.3276(6) 0.0210(8) Uani 1 2 d S T P . .
H2 H 0.464914 0.250000 0.346168 0.025 Uiso 1 2 calc R U P . .
C3 C 0.3355(2) 0.250000 0.1880(7) 0.0344(11) Uani 1 2 d S T P . .
H3 H 0.306300 0.250000 0.093249 0.041 Uiso 1 2 calc R U P . .
C4 C 0.3270(2) 0.250000 0.3822(7) 0.0393(13) Uani 1 2 d S T P . .
H4 H 0.290761 0.250000 0.446883 0.047 Uiso 1 2 calc R U P . .
C5 C 0.4256(2) 0.750000 1.0127(6) 0.0208(8) Uani 1 2 d S T P . .
H5 H 0.464837 0.750000 0.970254 0.025 Uiso 1 2 calc R U P . .
C6 C 0.33698(15) 0.6823(4) 1.1085(6) 0.0348(8) Uani 1 1 d . . . . .
H6 H 0.305537 0.626907 1.142389 0.042 Uiso 1 1 calc R U . . .
O7 O 0.56115(17) 0.250000 0.4725(6) 0.0399(9) Uani 1 2 d S T P . .
H7 H 0.584470 0.320200 0.452012 0.060 Uiso 1 1 d R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9755(17) . ?
Cu1 O2 2.0176(17) 1_556 ?
Cu1 O3 1.921(3) . ?
Cu1 O4 1.937(2) . ?
Cu1 O6 2.264(3) . ?
O1 N1 1.352(4) . ?
O2 N2 1.364(4) . ?
O3 N3 1.353(3) . ?
O4 C1 1.282(5) . ?
O5 C1 1.223(6) . ?
O6 H6A 0.8901 . ?
O6 H6B 0.8900 . ?
N1 C2 1.327(6) . ?
N1 C4 1.362(6) . ?
N2 C2 1.330(5) . ?
N2 C3 1.356(6) . ?
N3 C5 1.335(4) . ?
N3 C6 1.361(5) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.361(7) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C6 1.360(8) 7_575 ?
C6 H6 0.9300 . ?
O7 H7 0.8901 7_565 ?
O7 H7 0.8901 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 73.70(10) . 1_556 ?
O1 Cu1 O6 93.16(15) . . ?
O2 Cu1 O6 99.63(12) 1_556 . ?
O3 Cu1 O1 160.25(10) . . ?
O3 Cu1 O2 87.37(9) . 1_556 ?
O3 Cu1 O4 100.44(11) . . ?
O3 Cu1 O6 95.55(13) . . ?
O4 Cu1 O1 97.01(11) . . ?
O4 Cu1 O2 165.79(11) . 1_556 ?
O4 Cu1 O6 91.48(11) . . ?
Cu1 O1 Cu1 107.67(14) . 7_565 ?
N1 O1 Cu1 126.16(7) . 7_565 ?
N1 O1 Cu1 126.16(7) . . ?
Cu1 O2 Cu1 104.46(13) 7_564 1_554 ?
N2 O2 Cu1 114.42(14) . 7_564 ?
N2 O2 Cu1 114.42(14) . 1_554 ?
N3 O3 Cu1 120.80(19) . . ?
C1 O4 Cu1 110.6(3) . . ?
Cu1 O6 H6A 116.1 . . ?
Cu1 O6 H6B 114.5 . . ?
H6A O6 H6B 95.8 . . ?
O1 N1 C4 125.1(4) . . ?
C2 N1 O1 123.9(4) . . ?
C2 N1 C4 111.0(4) . . ?
C2 N2 O2 123.5(3) . . ?
C2 N2 C3 111.0(4) . . ?
C3 N2 O2 125.6(3) . . ?
O3 N3 C6 125.9(3) . . ?
C5 N3 O3 123.6(3) . . ?
C5 N3 C6 110.1(3) . . ?
O4 C1 H1 117.6 . . ?
O5 C1 O4 124.8(4) . . ?
O5 C1 H1 117.6 . . ?
N1 C2 N2 105.7(4) . . ?
N1 C2 H2 127.1 . . ?
N2 C2 H2 127.1 . . ?
N2 C3 H3 126.8 . . ?
N2 C3 C4 106.3(4) . . ?
C4 C3 H3 126.8 . . ?
N1 C4 H4 127.0 . . ?
C3 C4 N1 106.0(4) . . ?
C3 C4 H4 127.0 . . ?
N3 C5 N3 106.5(4) 7_575 . ?
N3 C5 H5 126.7 7_575 . ?
N3 C5 H5 126.7 . . ?
N3 C6 H6 126.7 . . ?
C6 C6 N3 106.6(2) 7_575 . ?
C6 C6 H6 126.7 7_575 . ?
H7 O7 H7 104.7 . 7_565 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 N1 C2 89.5(3) . . . . ?
Cu1 O1 N1 C2 -89.5(3) 7_565 . . . ?
Cu1 O1 N1 C4 90.5(3) 7_565 . . . ?
Cu1 O1 N1 C4 -90.5(3) . . . . ?
Cu1 O2 N2 C2 119.76(15) 7_564 . . . ?
Cu1 O2 N2 C2 -119.76(15) 1_554 . . . ?
Cu1 O2 N2 C3 -60.24(15) 7_564 . . . ?
Cu1 O2 N2 C3 60.24(15) 1_554 . . . ?
Cu1 O3 N3 C5 -95.6(4) . . . . ?
Cu1 O3 N3 C6 91.5(4) . . . . ?
Cu1 O4 C1 O5 1.5(6) . . . . ?
O1 N1 C2 N2 180.000(0) . . . . ?
O1 N1 C4 C3 180.000(0) . . . . ?
O2 N2 C2 N1 180.000(0) . . . . ?
O2 N2 C3 C4 180.000(0) . . . . ?
O3 N3 C5 N3 -173.79(19) . . . 7_575 ?
O3 N3 C6 C6 173.6(2) . . . 7_575 ?
N2 C3 C4 N1 0.000(0) . . . . ?
C2 N1 C4 C3 0.000(0) . . . . ?
C2 N2 C3 C4 0.000(0) . . . . ?
C3 N2 C2 N1 0.000(0) . . . . ?
C4 N1 C2 N2 0.000(0) . . . . ?
C5 N3 C6 C6 -0.1(3) . . . 7_575 ?
C6 N3 C5 N3 0.1(5) . . . 7_575 ?

_olex2_submission_special_instructions 'No special instructions were received'
