# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_170k
_database_code_depnum_ccdc_archive 'CCDC 2327404'
loop_
_audit_author_name
_audit_author_address
'Dubravka Matkovic-Calogovic'
;University of Zagreb, Faculty of Science
Croatia
;
_audit_update_record             
;
2024-01-22 deposited with the CCDC.	2024-11-19 downloaded from the CCDC.
;
_audit_creation_date             2023-12-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H28 Cu2 N8 O8, 2(H2 O)'
_chemical_formula_sum            'C18 H32 Cu2 N8 O10'
_chemical_formula_weight         647.60
_chemical_absolute_configuration syn
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      trigonal
_space_group_IT_number           152
_space_group_name_H-M_alt        'P 31 2 1'
_space_group_name_Hall           'P 31 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'y, x, -z'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'

_cell_length_a                   8.56884(6)
_cell_length_b                   8.56884(6)
_cell_length_c                   30.61946(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1947.03(3)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    30246
_cell_measurement_temperature    169.98(10)
_cell_measurement_theta_max      74.7530
_cell_measurement_theta_min      4.3220
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.761
_exptl_absorpt_coefficient_mu    2.620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.91a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'hexagonal plate'
_exptl_crystal_F_000             1002
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0039
-1 0 0 0.0438
-1 1 1 0.0480
0 -1 -1 0.0514
0 1 1 0.0618
1 0 1 0.0579
0 0 1 0.0219
2 -2 -1 0.0535

_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0097
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            48652
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.075
_diffrn_reflns_theta_min         4.332
_diffrn_ambient_temperature      170(1)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -121.00 -19.00   0.50    2.00    --  -42.63 -31.00 -13.00  204
  2  ω   -124.00 -16.00   0.50    4.00    --  -90.25  87.00-105.00  216
  3  ω     33.00 107.00   0.50    4.00    --  107.81-103.00-117.00  148
  4  ω     34.00 139.00   0.50    4.00    --  107.81 -81.00 -27.00  210
  5  ω    101.00 178.00   0.50    4.00    --  107.81  81.00  95.00  154
  6  ω    -26.00  38.00   0.50    2.00    --  -42.63  19.00   0.00  128
  7  ω   -117.00 -88.00   0.50    2.00    --  -42.63 -77.00  90.00   58
  8  ω   -117.00 -88.00   0.50    2.00    --  -42.63 -77.00   0.00   58
  9  ω     21.00 117.00   0.50    2.00    --   42.63  55.00 114.00  192
 10  ω     88.00 117.00   0.50    2.00    --   42.63  77.00-120.00   58
 11  ω     88.00 117.00   0.50    2.00    --   42.63  77.00 -60.00   58
 12  ω     88.00 117.00   0.50    2.00    --   42.63  77.00-150.00   58
 13  ω    -51.00 -14.00   0.50    4.00    --  -90.25  45.00 -90.00   74
 14  ω    -86.00 -16.00   0.50    4.00    --  -90.25 125.00-120.00  140
 15  ω     34.00  71.00   0.50    4.00    --  107.81 -61.00-120.00   74
 16  ω     34.00  71.00   0.50    4.00    --  107.81 -61.00 -30.00   74
 17  ω     34.00 105.00   0.50    4.00    --  107.81 -77.00  60.00  142
 18  ω     33.00 105.00   0.50    4.00    --  107.81 -95.00 -90.00  144
 19  ω     34.00 105.00   0.50    4.00    --  107.81 -77.00 150.00  142
 20  ω     84.00 178.00   0.50    4.00    --  107.81  30.00   0.00  188
 21  ω     34.00  71.00   0.50    4.00    --  107.81 -61.00-180.00   74
 22  ω     33.00 105.00   0.50    4.00    --  107.81 -95.00 -30.00  144
 23  ω     34.00  71.00   0.50    4.00    --  107.81 -61.00 -90.00   74
 24  ω     34.00 105.00   0.50    4.00    --  107.81 -77.00 120.00  142
 25  ω     86.00 178.00   0.50    4.00    --  107.81  45.00 120.00  184
 26  ω     84.00 178.00   0.50    4.00    --  107.81  30.00 -90.00  188
 27  ω     21.00 117.00   0.50    2.00    --   42.63  57.00  30.00  192
 28  ω     61.00 122.00   0.50    2.00    --   42.63-178.00 -90.00  122
 29  ω     21.00 117.00   0.50    2.00    --   42.63  57.00 -60.00  192
 30  ω     62.00 122.00   0.50    2.00    --   42.63 178.00-180.00  120
 31  ω     21.00 117.00   0.50    2.00    --   42.63  57.00-150.00  192
 32  ω     21.00 117.00   0.50    2.00    --   42.63  57.00-180.00  192
 33  ω   -164.00 -67.00   0.50    4.00    --  -90.25 -61.00 120.00  194
 34  ω    -51.00 -14.00   0.50    4.00    --  -90.25  45.00 120.00   74
 35  ω   -164.00 -67.00   0.50    4.00    --  -90.25 -61.00 -30.00  194
 36  ω   -164.00 -67.00   0.50    4.00    --  -90.25 -61.00  60.00  194
 37  ω   -164.00 -67.00   0.50    4.00    --  -90.25 -61.00-180.00  194
 38  ω   -164.00 -67.00   0.50    4.00    --  -90.25 -61.00   0.00  194
 39  ω   -164.00 -67.00   0.50    4.00    --  -90.25 -61.00 -90.00  194
 40  ω   -164.00 -67.00   0.50    4.00    --  -90.25 -61.00-120.00  194
 41  ω   -164.00 -67.00   0.50    4.00    --  -90.25 -61.00  90.00  194
 42  ω   -164.00 -67.00   0.50    4.00    --  -90.25 -61.00-150.00  194
 43  ω   -164.00 -67.00   0.50    4.00    --  -90.25 -61.00  30.00  194
 44  ω    -51.00 -14.00   0.50    4.00    --  -90.25  45.00  60.00   74
 45  ω   -164.00 -67.00   0.50    4.00    --  -90.25 -61.00 -60.00  194
 46  ω   -164.00 -67.00   0.50    4.00    --  -90.25 -61.00 150.00  194
 47  ω     84.00 178.00   0.50    4.00    --  107.81  30.00-150.00  188
 48  ω     84.00 178.00   0.50    4.00    --  107.81  30.00-180.00  188
 49  ω     86.00 178.00   0.50    4.00    --  107.81  45.00 -60.00  184
 50  ω     84.00 178.00   0.50    4.00    --  107.81  30.00  60.00  188
 51  ω     21.00 117.00   0.50    2.00    --   42.63  57.00-120.00  192
 52  ω     62.00 122.00   0.50    2.00    --   42.63 178.00  90.00  120
 53  ω     21.00 117.00   0.50    2.00    --   42.63  57.00  60.00  192
 54  ω     21.00 117.00   0.50    2.00    --   42.63  57.00   0.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2522
_reflns_number_total             2655
_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       'CrysAlisPro 1.171.43.91a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 42.53a 64-bit (release 15-04-2022))'
_computing_data_reduction        'CrysAlisPro 1.171.43.91a (Rigaku OD, 2023)'
_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         0.419
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 976 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.019(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0318
_refine_ls_restrained_S_all      1.057
_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)+(0.0304P)²+1.1468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0757
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 Cu1-N1A \\sim Cu1-N1B
 with sigma of 0.005
 N1A-C1A \\sim N1B-C1B
 with sigma of 0.005
 C2A-C3A \\sim C2B-C3B
 with sigma of 0.005
 C3A-O3A \\sim C3B-O3B
 with sigma of 0.005
 C3A-N2 \\sim C3B-N2
 with sigma of 0.005
 Cu1-HW1A \\sim Cu1-HW1B
 with sigma of 0.02
3. Restrained planarity
 N2, C3A, O3A, C2A
 with sigma of 0.1
 N2, C3B, O3B, C2B
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
N1A \\sim N1B: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 2A
C1A \\sim C1B: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 2A
C2A \\sim C2B: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 2A
C3A \\sim C3B: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 2A
O3A \\sim O3B: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 2A
5. Others
 Sof(O3B)=Sof(N1B)=Sof(H1BA)=Sof(H1BB)=Sof(C1B)=Sof(H1BC)=Sof(H1BD)=Sof(C2B)=
 Sof(H2BA)=Sof(H2BB)=Sof(C3B)=1-FVAR(1)
 Sof(O3A)=Sof(N1A)=Sof(H1AA)=Sof(H1AB)=Sof(C1A)=Sof(H1AC)=Sof(H1AD)=Sof(C2A)=
 Sof(H2AA)=Sof(H2AB)=Sof(C3A)=FVAR(1)
6.a Free rotating group:
 OW1(HW1A,HW1B), OW2(HW2A,HW2B)
6.b Ternary CH refined with riding coordinates:
 C5(H5)
6.c Secondary CH2 refined with riding coordinates:
 N1A(H1AA,H1AB), N1B(H1BA,H1BB), C1A(H1AC,H1AD), C1B(H1BC,H1BD), C2A(H2AA,
 H2AB), C2B(H2BA,H2BB), C6(H6A,H6B)
6.d Aromatic/amide H refined with riding coordinates:
 N4(H4), C8(H8), C9(H9)
;
_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 0.31605(8) 0.83330(9) 0.62878(2) 0.05519(18) Uani 1 1 d D . . . .
O1 O 0.3026(3) 1.0575(4) 0.62978(7) 0.0539(6) Uani 1 1 d . . . . .
O2 O 0.1774(5) 1.1896(4) 0.59381(10) 0.0718(8) Uani 1 1 d . . . . .
O3A O 0.3008(14) 0.7948(13) 0.49293(19) 0.058(2) Uani 0.601(11) 1 d D U P A 1
O3B O 0.3624(19) 0.8761(17) 0.4940(3) 0.055(3) Uani 0.399(11) 1 d D U P A 2
OW1 O 0.6308(6) 1.0021(7) 0.64727(8) 0.0863(11) Uani 1 1 d G . . . .
HW1A H 0.692652 1.026556 0.623146 0.129 Uiso 1 1 d DG U . . .
HW1B H 0.660661 0.933909 0.661827 0.129 Uiso 1 1 d DG U . . .
OW2 O 0.1148(6) 0.8355(6) 0.42692(10) 0.0885(12) Uani 1 1 d G . . . .
HW2A H 0.165494 0.949040 0.420122 0.133 Uiso 1 1 d G U . . .
HW2B H 0.175615 0.821403 0.447843 0.133 Uiso 1 1 d G U . . .
N1A N 0.3247(13) 0.6042(10) 0.6200(3) 0.057(2) Uani 0.601(11) 1 d D U P A 1
H1AA H 0.361502 0.576551 0.645265 0.069 Uiso 0.601(11) 1 calc R U P A 1
H1AB H 0.211737 0.512519 0.613955 0.069 Uiso 0.601(11) 1 calc R U P A 1
N1B N 0.3988(19) 0.6519(17) 0.6247(5) 0.069(4) Uani 0.399(11) 1 d D U P A 2
H1BA H 0.514796 0.701795 0.634065 0.083 Uiso 0.399(11) 1 calc R U P A 2
H1BB H 0.328591 0.554999 0.641867 0.083 Uiso 0.399(11) 1 calc R U P A 2
N2 N 0.2888(4) 0.8510(5) 0.56596(8) 0.0562(8) Uani 1 1 d D . . . .
N3 N -0.2375(4) 0.5557(4) 0.64213(8) 0.0538(8) Uani 1 1 d . . . . .
N4 N -0.1747(5) 0.5198(4) 0.57510(8) 0.0527(8) Uani 1 1 d . . . . .
H4 H -0.170333 0.465985 0.551044 0.063 Uiso 1 1 calc R U . . .
C1A C 0.4481(16) 0.619(3) 0.5841(4) 0.051(3) Uani 0.601(11) 1 d D U P A 1
H1AC H 0.469247 0.515592 0.585480 0.062 Uiso 0.601(11) 1 calc R U P A 1
H1AD H 0.565563 0.730848 0.587816 0.062 Uiso 0.601(11) 1 calc R U P A 1
C1B C 0.385(3) 0.594(4) 0.5784(5) 0.063(5) Uani 0.399(11) 1 d D U P A 2
H1BC H 0.434562 0.512012 0.575953 0.075 Uiso 0.399(11) 1 calc R U P A 2
H1BD H 0.256318 0.525323 0.570214 0.075 Uiso 0.399(11) 1 calc R U P A 2
C2A C 0.3695(10) 0.6216(10) 0.53955(17) 0.0473(18) Uani 0.601(11) 1 d D U P A 1
H2AA H 0.459347 0.638975 0.516924 0.057 Uiso 0.601(11) 1 calc R U P A 1
H2AB H 0.262045 0.501788 0.534544 0.057 Uiso 0.601(11) 1 calc R U P A 1
C2B C 0.4793(16) 0.7418(17) 0.5471(3) 0.050(3) Uani 0.399(11) 1 d D U P A 2
H2BA H 0.506632 0.692667 0.520733 0.060 Uiso 0.399(11) 1 calc R U P A 2
H2BB H 0.595864 0.831523 0.560111 0.060 Uiso 0.399(11) 1 calc R U P A 2
C3A C 0.3152(11) 0.7636(12) 0.53282(16) 0.046(2) Uani 0.601(11) 1 d D U P A 1
C3B C 0.3814(16) 0.8384(19) 0.5328(3) 0.055(4) Uani 0.399(11) 1 d D U P A 2
C4 C 0.2289(5) 1.0785(5) 0.59582(11) 0.0512(8) Uani 1 1 d . . . . .
C5 C 0.2049(5) 0.9588(5) 0.55657(9) 0.0475(8) Uani 1 1 d . . . . .
H5 H 0.266499 1.037353 0.530777 0.057 Uiso 1 1 calc R U . . .
C6 C 0.0037(5) 0.8367(5) 0.54571(9) 0.0434(7) Uani 1 1 d . . . . .
H6A H -0.051263 0.913047 0.540951 0.052 Uiso 1 1 calc R U . . .
H6B H -0.006963 0.771818 0.518120 0.052 Uiso 1 1 calc R U . . .
C7 C -0.0993(5) 0.7019(5) 0.58063(9) 0.0437(7) Uani 1 1 d . . . . .
C8 C -0.1417(5) 0.7210(5) 0.62243(10) 0.0493(8) Uani 1 1 d . . . . .
H8 H -0.109522 0.832846 0.635985 0.059 Uiso 1 1 calc R U . . .
C9 C -0.2565(6) 0.4368(6) 0.61233(10) 0.0580(10) Uani 1 1 d . . . . .
H9 H -0.319272 0.310040 0.616591 0.070 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.982(3) . ?
Cu1 OW1 2.405(5) . ?
Cu1 N1A 2.019(5) . ?
Cu1 N1B 2.009(7) . ?
Cu1 N2 1.953(3) . ?
Cu1 N3 1.998(3) 6_556 ?
O1 C4 1.275(4) . ?
O2 C4 1.235(5) . ?
O3A C3A 1.269(5) . ?
O3B C3B 1.262(6) . ?
OW1 HW1A 0.8713 . ?
OW1 HW1B 0.8691 . ?
OW2 HW2A 0.8694 . ?
OW2 HW2B 0.8714 . ?
N1A H1AA 0.9100 . ?
N1A H1AB 0.9100 . ?
N1A C1A 1.487(7) . ?
N1B H1BA 0.9100 . ?
N1B H1BB 0.9100 . ?
N1B C1B 1.486(8) . ?
N2 C3A 1.346(6) . ?
N2 C3B 1.326(7) . ?
N2 C5 1.455(5) . ?
N3 C8 1.372(5) . ?
N3 C9 1.315(5) . ?
N4 H4 0.8800 . ?
N4 C7 1.368(5) . ?
N4 C9 1.341(4) . ?
C1A H1AC 0.9900 . ?
C1A H1AD 0.9900 . ?
C1A C2A 1.526(13) . ?
C1B H1BC 0.9900 . ?
C1B H1BD 0.9900 . ?
C1B C2B 1.47(3) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C2A C3A 1.518(7) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C2B C3B 1.509(8) . ?
C4 C5 1.526(5) . ?
C5 H5 1.0000 . ?
C5 C6 1.541(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.496(5) . ?
C7 C8 1.362(4) . ?
C8 H8 0.9500 . ?
C9 H9 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
O1 Cu1 OW1 90.27(12) . . ?
O1 Cu1 N1A 173.2(3) . . ?
O1 Cu1 N1B 164.8(5) . . ?
O1 Cu1 N3 88.53(12) . 6_556 ?
N1A Cu1 OW1 92.3(3) . . ?
N1B Cu1 OW1 75.9(4) . . ?
N2 Cu1 O1 82.68(12) . . ?
N2 Cu1 OW1 109.07(12) . . ?
N2 Cu1 N1A 90.5(3) . . ?
N2 Cu1 N1B 95.8(4) . . ?
N2 Cu1 N3 155.85(13) . 6_556 ?
N3 Cu1 OW1 93.35(12) 6_556 . ?
N3 Cu1 N1A 97.6(3) 6_556 . ?
N3 Cu1 N1B 98.3(5) 6_556 . ?
C4 O1 Cu1 113.4(2) . . ?
Cu1 OW1 HW1A 108.0 . . ?
Cu1 OW1 HW1B 109.6 . . ?
HW1A OW1 HW1B 104.4 . . ?
HW2A OW2 HW2B 109.4 . . ?
Cu1 N1A H1AA 109.1 . . ?
Cu1 N1A H1AB 109.1 . . ?
H1AA N1A H1AB 107.8 . . ?
C1A N1A Cu1 112.7(10) . . ?
C1A N1A H1AA 109.1 . . ?
C1A N1A H1AB 109.1 . . ?
Cu1 N1B H1BA 110.0 . . ?
Cu1 N1B H1BB 110.0 . . ?
H1BA N1B H1BB 108.4 . . ?
C1B N1B Cu1 108.5(13) . . ?
C1B N1B H1BA 110.0 . . ?
C1B N1B H1BB 110.0 . . ?
C3A N2 Cu1 129.7(3) . . ?
C3A N2 C5 118.6(3) . . ?
C3B N2 Cu1 130.4(5) . . ?
C3B N2 C5 114.0(5) . . ?
C5 N2 Cu1 111.1(2) . . ?
C8 N3 Cu1 124.7(2) . 6_556 ?
C9 N3 Cu1 129.4(3) . 6_556 ?
C9 N3 C8 105.8(3) . . ?
C7 N4 H4 125.6 . . ?
C9 N4 H4 125.6 . . ?
C9 N4 C7 108.9(3) . . ?
N1A C1A H1AC 109.4 . . ?
N1A C1A H1AD 109.4 . . ?
N1A C1A C2A 111.2(9) . . ?
H1AC C1A H1AD 108.0 . . ?
C2A C1A H1AC 109.4 . . ?
C2A C1A H1AD 109.4 . . ?
N1B C1B H1BC 108.5 . . ?
N1B C1B H1BD 108.5 . . ?
H1BC C1B H1BD 107.5 . . ?
C2B C1B N1B 115(2) . . ?
C2B C1B H1BC 108.5 . . ?
C2B C1B H1BD 108.5 . . ?
C1A C2A H2AA 108.1 . . ?
C1A C2A H2AB 108.1 . . ?
H2AA C2A H2AB 107.3 . . ?
C3A C2A C1A 116.6(8) . . ?
C3A C2A H2AA 108.1 . . ?
C3A C2A H2AB 108.1 . . ?
C1B C2B H2BA 108.2 . . ?
C1B C2B H2BB 108.2 . . ?
C1B C2B C3B 116.5(12) . . ?
H2BA C2B H2BB 107.3 . . ?
C3B C2B H2BA 108.2 . . ?
C3B C2B H2BB 108.2 . . ?
O3A C3A N2 123.1(6) . . ?
O3A C3A C2A 113.6(6) . . ?
N2 C3A C2A 123.2(5) . . ?
O3B C3B N2 122.7(10) . . ?
O3B C3B C2B 126.3(9) . . ?
N2 C3B C2B 110.1(6) . . ?
O1 C4 C5 117.2(4) . . ?
O2 C4 O1 122.8(4) . . ?
O2 C4 C5 119.9(3) . . ?
N2 C5 C4 109.1(3) . . ?
N2 C5 H5 108.8 . . ?
N2 C5 C6 110.6(3) . . ?
C4 C5 H5 108.8 . . ?
C4 C5 C6 110.8(3) . . ?
C6 C5 H5 108.8 . . ?
C5 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 C5 113.5(3) . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
N4 C7 C6 123.5(3) . . ?
C8 C7 N4 104.5(3) . . ?
C8 C7 C6 132.0(3) . . ?
N3 C8 H8 124.9 . . ?
C7 C8 N3 110.3(3) . . ?
C7 C8 H8 124.9 . . ?
N3 C9 N4 110.5(4) . . ?
N3 C9 H9 124.8 . . ?
N4 C9 H9 124.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
OW1 HW1A OW2 0.87 1.87 2.734(4) 171.4 4_566 yes
OW2 HW2A O2 0.87 1.91 2.742(5) 159.6 4_466 yes
OW2 HW2B O3A 0.87 1.83 2.702(8) 178.3 . yes
OW2 HW2B O3B 0.87 2.01 2.847(12) 161.3 . yes
N4 H4 O3A 0.88 1.87 2.728(9) 165.7 4_456 yes
N4 H4 O3B 0.88 1.79 2.661(13) 169.7 4_456 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C4 O2 165.9(3) . . . . ?
Cu1 O1 C4 C5 -14.0(4) . . . . ?
Cu1 N1A C1A C2A -72.0(14) . . . . ?
Cu1 N1B C1B C2B 54(2) . . . . ?
Cu1 N2 C3A O3A -176.5(6) . . . . ?
Cu1 N2 C3A C2A 2.0(10) . . . . ?
Cu1 N2 C3B O3B -170.5(8) . . . . ?
Cu1 N2 C3B C2B 20.2(14) . . . . ?
Cu1 N2 C5 C4 21.0(4) . . . . ?
Cu1 N2 C5 C6 -101.2(3) . . . . ?
Cu1 N3 C8 C7 176.1(3) 6_556 . . . ?
Cu1 N3 C9 N4 -176.2(3) 6_556 . . . ?
O1 C4 C5 N2 -4.6(4) . . . . ?
O1 C4 C5 C6 117.4(3) . . . . ?
O2 C4 C5 N2 175.5(4) . . . . ?
O2 C4 C5 C6 -62.5(4) . . . . ?
N1A C1A C2A C3A 54.6(15) . . . . ?
N1B C1B C2B C3B -81.4(19) . . . . ?
N2 C5 C6 C7 55.7(3) . . . . ?
N4 C7 C8 N3 1.1(4) . . . . ?
C1A C2A C3A O3A 160.8(9) . . . . ?
C1A C2A C3A N2 -17.8(11) . . . . ?
C1B C2B C3B O3B -132.4(14) . . . . ?
C1B C2B C3B N2 36.3(15) . . . . ?
C3A N2 C5 C4 -166.8(5) . . . . ?
C3A N2 C5 C6 71.1(6) . . . . ?
C3B N2 C5 C4 -137.8(8) . . . . ?
C3B N2 C5 C6 100.0(8) . . . . ?
C4 C5 C6 C7 -65.4(4) . . . . ?
C5 N2 C3A O3A 12.9(10) . . . . ?
C5 N2 C3A C2A -168.6(6) . . . . ?
C5 N2 C3B O3B -16.8(15) . . . . ?
C5 N2 C3B C2B 173.9(7) . . . . ?
C5 C6 C7 N4 -114.0(4) . . . . ?
C5 C6 C7 C8 66.2(5) . . . . ?
C6 C7 C8 N3 -179.1(4) . . . . ?
C7 N4 C9 N3 -0.4(5) . . . . ?
C8 N3 C9 N4 1.0(5) . . . . ?
C9 N3 C8 C7 -1.3(5) . . . . ?
C9 N4 C7 C6 179.7(4) . . . . ?
C9 N4 C7 C8 -0.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_270
_database_code_depnum_ccdc_archive 'CCDC 2327405'
loop_
_audit_author_name
_audit_author_address
'Dubravka Matkovic-Calogovic'
;University of Zagreb, Faculty of Science
Croatia
;
_audit_update_record             
;
2024-01-22 deposited with the CCDC.	2024-11-19 downloaded from the CCDC.
;
_audit_creation_date             2023-12-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H28 Cu2 N8 O8, 2(H2 O)'
_chemical_formula_sum            'C18 H32 Cu2 N8 O10'
_chemical_formula_weight         647.60
_chemical_absolute_configuration syn
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      trigonal
_space_group_IT_number           152
_space_group_name_H-M_alt        'P 31 2 1'
_space_group_name_Hall           'P 31 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'y, x, -z'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'

_cell_length_a                   8.61755(19)
_cell_length_b                   8.61755(19)
_cell_length_c                   30.5882(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1967.22(9)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    5065
_cell_measurement_temperature    270(1)
_cell_measurement_theta_min      5.9400
_cell_measurement_theta_max      76.1300
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.729
_exptl_absorpt_coefficient_mu    2.593
_exptl_absorpt_correction_T_min  0.92440
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.91a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'hexagonal plate'
_exptl_crystal_F_000             1002
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            7754
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.126
_diffrn_reflns_theta_min         4.336
_diffrn_ambient_temperature      270.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.554
_reflns_Friedel_fraction_full    0.888
_reflns_Friedel_fraction_max     0.801
_reflns_number_gt                2284
_reflns_number_total             2498
_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         0.404
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 768 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2498
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0313
_refine_ls_restrained_S_all      1.041
_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)+(0.0493P)²+0.2151P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0849
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 Cu1-N1A \\sim Cu1-N1B
 with sigma of 0.005
 N1A-C1A \\sim N1B-C1B
 with sigma of 0.005
 C2A-C3A \\sim C2B-C3B
 with sigma of 0.005
 C3A-O3A \\sim C3B-O3B
 with sigma of 0.005
 C3A-N2 \\sim C3B-N2
 with sigma of 0.005
 Cu1-HW1A \\sim Cu1-HW1B
 with sigma of 0.02
3. Restrained planarity
 N2, C3A, O3A, C2A
 with sigma of 0.1
 N2, C3B, O3B, C2B
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
N1A \\sim N1B: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 2A
C1A \\sim C1B: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 2A
C2A \\sim C2B: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 2A
C3A \\sim C3B: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 2A
O3A \\sim O3B: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 2A
5. Others
 Sof(O3B)=Sof(N1B)=Sof(H1BA)=Sof(H1BB)=Sof(C1B)=Sof(H1BC)=Sof(H1BD)=Sof(C2B)=
 Sof(H2BA)=Sof(H2BB)=Sof(C3B)=1-FVAR(1)
 Sof(O3A)=Sof(N1A)=Sof(H1AA)=Sof(H1AB)=Sof(C1A)=Sof(H1AC)=Sof(H1AD)=Sof(C2A)=
 Sof(H2AA)=Sof(H2AB)=Sof(C3A)=FVAR(1)
6.a Free rotating group:
 OW1(HW1A,HW1B), OW2(HW2A,HW2B)
6.b Ternary CH refined with riding coordinates:
 C5(H5)
6.c Secondary CH2 refined with riding coordinates:
 N1A(H1AA,H1AB), N1B(H1BA,H1BB), C1A(H1AC,H1AD), C1B(H1BC,H1BD), C2A(H2AA,
 H2AB), C2B(H2BA,H2BB), C6(H6A,H6B)
6.d Aromatic/amide H refined with riding coordinates:
 N4(H4), C8(H8), C9(H9)
;
_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 0.31708(7) 0.83525(8) 0.62900(2) 0.05221(18) Uani 1 1 d D . . . .
O1 O 0.3021(3) 1.0569(4) 0.63001(6) 0.0538(6) Uani 1 1 d . . . . .
O2 O 0.1752(5) 1.1860(5) 0.59436(10) 0.0758(9) Uani 1 1 d . . . . .
O3A O 0.3028(18) 0.7969(18) 0.4939(2) 0.066(3) Uani 0.540(13) 1 d D U P A 1
O3B O 0.3608(19) 0.8706(19) 0.4936(3) 0.059(3) Uani 0.460(13) 1 d D U P A 2
OW1 O 0.6369(6) 1.0081(7) 0.64720(9) 0.0907(12) Uani 1 1 d G . . . .
HW1A H 0.696377 1.026060 0.622865 0.136 Uiso 1 1 d DG U . . .
HW1B H 0.662790 0.938118 0.662286 0.136 Uiso 1 1 d DG U . . .
OW2 O 0.1209(7) 0.8408(7) 0.42709(11) 0.0960(14) Uani 1 1 d G . . . .
HW2A H 0.160436 0.955904 0.428709 0.144 Uiso 1 1 d G U . . .
HW2B H 0.162758 0.808305 0.449089 0.144 Uiso 1 1 d G U . . .
N1A N 0.3272(17) 0.6088(12) 0.6196(4) 0.065(3) Uani 0.540(13) 1 d D U P A 1
H1AA H 0.362721 0.581213 0.644232 0.078 Uiso 0.540(13) 1 calc R U P A 1
H1AB H 0.217564 0.519637 0.613487 0.078 Uiso 0.540(13) 1 calc R U P A 1
N1B N 0.399(2) 0.6542(17) 0.6253(5) 0.065(3) Uani 0.460(13) 1 d D U P A 2
H1BA H 0.512894 0.703989 0.633774 0.078 Uiso 0.460(13) 1 calc R U P A 2
H1BB H 0.332953 0.562238 0.642916 0.078 Uiso 0.460(13) 1 calc R U P A 2
N2 N 0.2892(4) 0.8521(5) 0.56629(8) 0.0530(8) Uani 1 1 d D . . . .
N3 N -0.2395(4) 0.5559(4) 0.64183(8) 0.0522(7) Uani 1 1 d . . . . .
N4 N -0.1732(5) 0.5216(4) 0.57500(8) 0.0533(8) Uani 1 1 d . . . . .
H4 H -0.167667 0.469742 0.551517 0.064 Uiso 1 1 calc R U . . .
C1A C 0.4504(18) 0.624(3) 0.5836(4) 0.057(3) Uani 0.540(13) 1 d D U P A 1
H1AC H 0.473293 0.524754 0.585312 0.068 Uiso 0.540(13) 1 calc R U P A 1
H1AD H 0.563735 0.734438 0.586882 0.068 Uiso 0.540(13) 1 calc R U P A 1
C1B C 0.381(3) 0.590(3) 0.5794(5) 0.064(4) Uani 0.460(13) 1 d D U P A 2
H1BC H 0.254837 0.521472 0.572130 0.077 Uiso 0.460(13) 1 calc R U P A 2
H1BD H 0.429520 0.510006 0.577490 0.077 Uiso 0.460(13) 1 calc R U P A 2
C2A C 0.3692(14) 0.6221(14) 0.5397(2) 0.054(2) Uani 0.540(13) 1 d D U P A 1
H2AA H 0.263326 0.505571 0.535608 0.064 Uiso 0.540(13) 1 calc R U P A 1
H2AB H 0.454381 0.636735 0.517096 0.064 Uiso 0.540(13) 1 calc R U P A 1
C2B C 0.4736(16) 0.7363(17) 0.5465(2) 0.053(3) Uani 0.460(13) 1 d D U P A 2
H2BA H 0.496888 0.685801 0.520654 0.063 Uiso 0.460(13) 1 calc R U P A 2
H2BB H 0.588566 0.824813 0.558382 0.063 Uiso 0.460(13) 1 calc R U P A 2
C3A C 0.3169(15) 0.7661(15) 0.5336(2) 0.053(3) Uani 0.540(13) 1 d D U P A 1
C3B C 0.3732(17) 0.831(2) 0.5325(2) 0.055(4) Uani 0.460(13) 1 d D U P A 2
C4 C 0.2276(5) 1.0767(5) 0.59603(10) 0.0500(8) Uani 1 1 d . . . . .
C5 C 0.2036(5) 0.9574(5) 0.55687(9) 0.0453(7) Uani 1 1 d . . . . .
H5 H 0.263449 1.034207 0.531595 0.054 Uiso 1 1 calc R U . . .
C6 C 0.0051(5) 0.8371(5) 0.54589(9) 0.0433(7) Uani 1 1 d . . . . .
H6A H -0.048236 0.911765 0.541253 0.052 Uiso 1 1 calc R U . . .
H6B H -0.004808 0.774594 0.518750 0.052 Uiso 1 1 calc R U . . .
C7 C -0.0987(5) 0.7020(5) 0.58064(9) 0.0425(7) Uani 1 1 d . . . . .
C8 C -0.1428(5) 0.7209(5) 0.62242(10) 0.0473(8) Uani 1 1 d . . . . .
H8 H -0.111831 0.829599 0.635748 0.057 Uiso 1 1 calc R U . . .
C9 C -0.2566(6) 0.4382(5) 0.61204(10) 0.0581(9) Uani 1 1 d . . . . .
H9 H -0.317761 0.314736 0.616087 0.070 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.978(3) . ?
Cu1 N1A 2.017(6) . ?
Cu1 N1B 2.012(6) . ?
Cu1 N2 1.948(2) . ?
Cu1 N3 1.998(2) 6_556 ?
O1 C4 1.277(4) . ?
O2 C4 1.233(5) . ?
O3A C3A 1.261(6) . ?
O3B C3B 1.255(6) . ?
OW1 HW1A 0.8726 . ?
OW1 HW1B 0.8720 . ?
OW2 HW2A 0.8741 . ?
OW2 HW2B 0.8733 . ?
N1A H1AA 0.8900 . ?
N1A H1AB 0.8900 . ?
N1A C1A 1.487(8) . ?
N1B H1BA 0.8900 . ?
N1B H1BB 0.8900 . ?
N1B C1B 1.487(8) . ?
N2 C3A 1.337(6) . ?
N2 C3B 1.325(6) . ?
N2 C5 1.456(4) . ?
N3 C8 1.372(5) . ?
N3 C9 1.316(5) . ?
N4 H4 0.8600 . ?
N4 C7 1.364(5) . ?
N4 C9 1.341(4) . ?
C1A H1AC 0.9700 . ?
C1A H1AD 0.9700 . ?
C1A C2A 1.511(17) . ?
C1B H1BC 0.9700 . ?
C1B H1BD 0.9700 . ?
C1B C2B 1.49(3) . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C2A C3A 1.529(8) . ?
C2B H2BA 0.9700 . ?
C2B H2BB 0.9700 . ?
C2B C3B 1.521(8) . ?
C4 C5 1.523(5) . ?
C5 H5 0.9800 . ?
C5 C6 1.530(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.498(5) . ?
C7 C8 1.366(4) . ?
C8 H8 0.9300 . ?
C9 H9 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 N1A 172.6(4) . . ?
O1 Cu1 N1B 165.3(5) . . ?
O1 Cu1 N3 88.45(12) . 6_556 ?
N2 Cu1 O1 82.72(11) . . ?
N2 Cu1 N1A 89.9(4) . . ?
N2 Cu1 N1B 96.1(4) . . ?
N2 Cu1 N3 155.80(13) . 6_556 ?
N3 Cu1 N1A 98.2(4) 6_556 . ?
N3 Cu1 N1B 97.9(4) 6_556 . ?
C4 O1 Cu1 113.3(2) . . ?
HW1A OW1 HW1B 104.1 . . ?
HW2A OW2 HW2B 109.3 . . ?
Cu1 N1A H1AA 108.9 . . ?
Cu1 N1A H1AB 108.9 . . ?
H1AA N1A H1AB 107.7 . . ?
C1A N1A Cu1 113.3(12) . . ?
C1A N1A H1AA 108.9 . . ?
C1A N1A H1AB 108.9 . . ?
Cu1 N1B H1BA 109.8 . . ?
Cu1 N1B H1BB 109.8 . . ?
H1BA N1B H1BB 108.3 . . ?
C1B N1B Cu1 109.3(12) . . ?
C1B N1B H1BA 109.8 . . ?
C1B N1B H1BB 109.8 . . ?
C3A N2 Cu1 129.3(4) . . ?
C3A N2 C5 119.0(4) . . ?
C3B N2 Cu1 131.5(4) . . ?
C3B N2 C5 114.3(4) . . ?
C5 N2 Cu1 111.18(19) . . ?
C8 N3 Cu1 124.3(2) . 6_556 ?
C9 N3 Cu1 129.6(3) . 6_556 ?
C9 N3 C8 106.0(3) . . ?
C7 N4 H4 125.5 . . ?
C9 N4 H4 125.5 . . ?
C9 N4 C7 108.9(3) . . ?
N1A C1A H1AC 109.6 . . ?
N1A C1A H1AD 109.6 . . ?
N1A C1A C2A 110.5(11) . . ?
H1AC C1A H1AD 108.1 . . ?
C2A C1A H1AC 109.6 . . ?
C2A C1A H1AD 109.6 . . ?
N1B C1B H1BC 108.7 . . ?
N1B C1B H1BD 108.7 . . ?
N1B C1B C2B 114.2(19) . . ?
H1BC C1B H1BD 107.6 . . ?
C2B C1B H1BC 108.7 . . ?
C2B C1B H1BD 108.7 . . ?
C1A C2A H2AA 108.5 . . ?
C1A C2A H2AB 108.5 . . ?
C1A C2A C3A 115.1(10) . . ?
H2AA C2A H2AB 107.5 . . ?
C3A C2A H2AA 108.5 . . ?
C3A C2A H2AB 108.5 . . ?
C1B C2B H2BA 108.3 . . ?
C1B C2B H2BB 108.3 . . ?
C1B C2B C3B 115.9(11) . . ?
H2BA C2B H2BB 107.4 . . ?
C3B C2B H2BA 108.3 . . ?
C3B C2B H2BB 108.3 . . ?
O3A C3A N2 122.7(9) . . ?
O3A C3A C2A 112.9(8) . . ?
N2 C3A C2A 124.4(6) . . ?
O3B C3B N2 125.3(10) . . ?
O3B C3B C2B 124.0(9) . . ?
N2 C3B C2B 110.5(6) . . ?
O1 C4 C5 117.2(3) . . ?
O2 C4 O1 122.4(3) . . ?
O2 C4 C5 120.3(3) . . ?
N2 C5 C4 108.9(3) . . ?
N2 C5 H5 108.5 . . ?
N2 C5 C6 111.3(3) . . ?
C4 C5 H5 108.5 . . ?
C4 C5 C6 111.0(3) . . ?
C6 C5 H5 108.5 . . ?
C5 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 C5 113.7(3) . . ?
C7 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
N4 C7 C6 123.7(3) . . ?
N4 C7 C8 104.7(3) . . ?
C8 C7 C6 131.6(3) . . ?
N3 C8 H8 125.0 . . ?
C7 C8 N3 110.0(3) . . ?
C7 C8 H8 125.0 . . ?
N3 C9 N4 110.4(3) . . ?
N3 C9 H9 124.8 . . ?
N4 C9 H9 124.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
OW1 HW1A OW2 0.87 1.88 2.737(5) 166.7 4_566 yes
OW2 HW2A O2 0.87 1.92 2.726(6) 151.9 4_466 yes
OW2 HW2B O3A 0.87 1.86 2.714(10) 165.3 . yes
OW2 HW2B O3B 0.87 2.03 2.820(12) 149.1 . yes
N4 H4 O3A 0.86 1.91 2.753(12) 165.7 4_456 yes
N4 H4 O3B 0.86 1.79 2.645(14) 171.6 4_456 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C4 O2 165.6(3) . . . . ?
Cu1 O1 C4 C5 -13.9(4) . . . . ?
Cu1 N1A C1A C2A -73.5(17) . . . . ?
Cu1 N1B C1B C2B 54.1(19) . . . . ?
Cu1 N2 C3A O3A -176.1(8) . . . . ?
Cu1 N2 C3A C2A 3.7(14) . . . . ?
Cu1 N2 C3B O3B -169.3(9) . . . . ?
Cu1 N2 C3B C2B 16.3(15) . . . . ?
Cu1 N2 C5 C4 21.3(3) . . . . ?
Cu1 N2 C5 C6 -101.4(3) . . . . ?
Cu1 N3 C8 C7 175.1(3) 6_556 . . . ?
Cu1 N3 C9 N4 -175.1(3) 6_556 . . . ?
O1 C4 C5 N2 -4.9(4) . . . . ?
O1 C4 C5 C6 118.1(3) . . . . ?
O2 C4 C5 N2 175.5(4) . . . . ?
O2 C4 C5 C6 -61.5(4) . . . . ?
N1A C1A C2A C3A 56.1(18) . . . . ?
N1B C1B C2B C3B -80.7(18) . . . . ?
N2 C5 C6 C7 55.8(3) . . . . ?
N4 C7 C8 N3 0.9(4) . . . . ?
C1A C2A C3A O3A 159.5(11) . . . . ?
C1A C2A C3A N2 -20.3(15) . . . . ?
C1B C2B C3B O3B -136.4(14) . . . . ?
C1B C2B C3B N2 38.1(15) . . . . ?
C3A N2 C5 C4 -166.4(7) . . . . ?
C3A N2 C5 C6 70.8(7) . . . . ?
C3B N2 C5 C4 -141.2(8) . . . . ?
C3B N2 C5 C6 96.0(8) . . . . ?
C4 C5 C6 C7 -65.8(4) . . . . ?
C5 N2 C3A O3A 13.3(13) . . . . ?
C5 N2 C3A C2A -167.0(8) . . . . ?
C5 N2 C3B O3B -11.2(16) . . . . ?
C5 N2 C3B C2B 174.4(7) . . . . ?
C5 C6 C7 N4 -113.8(4) . . . . ?
C5 C6 C7 C8 66.8(5) . . . . ?
C6 C7 C8 N3 -179.6(4) . . . . ?
C7 N4 C9 N3 -0.2(5) . . . . ?
C8 N3 C9 N4 0.8(5) . . . . ?
C9 N3 C8 C7 -1.0(5) . . . . ?
C9 N4 C7 C6 -179.9(4) . . . . ?
C9 N4 C7 C8 -0.4(4) . . . . ?

_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_2_100k
_database_code_depnum_ccdc_archive 'CCDC 2327414'
loop_
_audit_author_name
_audit_author_address
'Dubravka Matkovic-Calogovic'
;University of Zagreb, Faculty of Science
Croatia
;
_audit_update_record             
;
2024-01-22 deposited with the CCDC.	2024-11-19 downloaded from the CCDC.
;
_audit_creation_date             2024-01-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C18 H24 Cu2 N8 O6, 2(C0.703 H3.11 O), 0.593(O)'
_chemical_formula_sum            'C19.41 H30.22 Cu2 N8 O8.59'
_chemical_formula_weight         ?
_chemical_absolute_configuration syn
_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 0.0030 0.0020 '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 0.3450 1.2550 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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           23
_space_group_name_H-M_alt        'I 2 2 2'
_space_group_name_Hall           'I 2 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x, -y, -z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   12.08960(8)
_cell_length_b                   20.35323(15)
_cell_length_c                   13.73806(9)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_volume                     3380.42(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18279
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      30.0060
_cell_measurement_theta_min      1.9390
_cell_oxdiff_angle_alpha         90.048(3)
_cell_oxdiff_angle_beta          90.041(4)
_cell_oxdiff_angle_gamma         89.992(3)
_cell_oxdiff_length_a            12.0888(6)
_cell_oxdiff_length_b            20.3534(4)
_cell_oxdiff_length_c            13.7389(7)
_cell_oxdiff_measurement_reflns_used 18284
_cell_oxdiff_volume              3380.4(2)
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.255
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             ?
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 0.944
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29910
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         1.930
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'Dectris Pilatus'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ   -180.00 180.00   1.00    0.50   0.00   0.00   0.00    --   360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0425063000
_diffrn_orient_matrix_UB_12      -0.0044604000
_diffrn_orient_matrix_UB_13      0.0339289000
_diffrn_orient_matrix_UB_21      0.0355078000
_diffrn_orient_matrix_UB_22      0.0101338000
_diffrn_orient_matrix_UB_23      0.0373749000
_diffrn_orient_matrix_UB_31      -0.0168851000
_diffrn_orient_matrix_UB_32      0.0325611000
_diffrn_orient_matrix_UB_33      -0.0069380000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_source                   synchrotron
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                4983
_reflns_number_total             4990
_reflns_odcompleteness_completeness 98.05
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.00
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       ?
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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         0.432
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Flack x determined using 2249 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.024(5)
_refine_ls_extinction_coef       0.0240(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         4990
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0296
_refine_ls_restrained_S_all      1.047
_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)+(0.0522P)²+2.3407P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0805
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O4-C10
 1.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O4 \\sim C10: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
within 2A
4. Rigid body (RIGU) restrains
 O4, C10
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=1-FVAR(1)
 Sof(O2W)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C5(H5)
6.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C1(H1C,H1D), C2(H2A,H2B), C6(H6A,H6B)
6.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C8(H8), C9(H9)
6.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
6.e Idealised tetrahedral OH refined as rotating group:
 O4(H4A)
;
_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
Cu Cu 0.40614(2) 0.67631(2) 0.65744(2) 0.02267(10) Uani 1 1 d . . . . .
O1 O 0.34670(12) 0.58558(8) 0.64908(14) 0.0247(3) Uani 1 1 d . . . . .
O2 O 0.19097(14) 0.53091(10) 0.61879(19) 0.0366(4) Uani 1 1 d . . . . .
O3 O 0.10193(19) 0.76824(11) 0.63591(17) 0.0412(5) Uani 1 1 d . . . . .
N1 N 0.4573(2) 0.76589(12) 0.6949(2) 0.0359(5) Uani 1 1 d . . . . .
H1A H 0.518171 0.762214 0.733541 0.043 Uiso 1 1 calc R U . . .
H1B H 0.477411 0.788207 0.640318 0.043 Uiso 1 1 calc R U . . .
N2 N 0.25227(15) 0.70180(10) 0.64503(15) 0.0241(3) Uani 1 1 d . . . . .
N3 N 0.44444(15) 0.64792(10) 0.38020(14) 0.0221(3) Uani 1 1 d . . . . .
N4 N 0.30394(15) 0.58165(10) 0.40679(16) 0.0237(3) Uani 1 1 d . . . . .
H4 H 0.263399 0.545746 0.407503 0.028 Uiso 1 1 calc R U . . .
C1 C 0.3718(3) 0.80378(15) 0.7471(2) 0.0389(6) Uani 1 1 d . . . . .
H1C H 0.403939 0.845952 0.769175 0.047 Uiso 1 1 calc R U . . .
H1D H 0.348427 0.778936 0.805526 0.047 Uiso 1 1 calc R U . . .
C2 C 0.2722(3) 0.81756(14) 0.6851(2) 0.0383(6) Uani 1 1 d . . . . .
H2A H 0.297378 0.840634 0.625663 0.046 Uiso 1 1 calc R U . . .
H2B H 0.223569 0.848188 0.721200 0.046 Uiso 1 1 calc R U . . .
C3 C 0.2034(2) 0.75897(12) 0.6541(2) 0.0299(4) Uani 1 1 d . . . . .
C4 C 0.24483(18) 0.58340(11) 0.62931(18) 0.0245(4) Uani 1 1 d . . . . .
C5 C 0.18509(17) 0.64793(12) 0.60912(17) 0.0242(4) Uani 1 1 d . . . . .
H5 H 0.111851 0.648011 0.642953 0.029 Uiso 1 1 calc R U . . .
C6 C 0.16719(17) 0.65221(12) 0.49712(18) 0.0257(4) Uani 1 1 d . . . . .
H6A H 0.113258 0.618269 0.476811 0.031 Uiso 1 1 calc R U . . .
H6B H 0.135971 0.695756 0.480498 0.031 Uiso 1 1 calc R U . . .
C7 C 0.27292(17) 0.64245(11) 0.44306(16) 0.0230(4) Uani 1 1 d . . . . .
C8 C 0.36095(18) 0.68306(11) 0.42562(16) 0.0232(4) Uani 1 1 d . . . . .
H8 H 0.364282 0.728345 0.442104 0.028 Uiso 1 1 calc R U . . .
C9 C 0.40624(19) 0.58703(10) 0.37050(16) 0.0237(4) Uani 1 1 d . . . . .
H9 H 0.446306 0.551938 0.341585 0.028 Uiso 1 1 calc R U . . .
O4 O 0.4501(3) 0.64066(17) 0.8286(2) 0.0599(8) Uani 1 1 d D U . . .
H4A H 0.504069 0.665165 0.841315 0.090 Uiso 1 1 calc R U . . .
O2W O 0.3089(9) 0.6665(8) 0.9568(9) 0.076(5) Uani 0.297(14) 1 d . . P A -1
C10 C 0.3632(6) 0.6504(4) 0.9019(5) 0.064(2) Uani 0.703(14) 1 d D U P . .
H10A H 0.292517 0.658691 0.869241 0.097 Uiso 0.703(14) 1 calc R U P . .
H10B H 0.382226 0.688096 0.942994 0.097 Uiso 0.703(14) 1 calc R U P . .
H10C H 0.356965 0.610915 0.942337 0.097 Uiso 0.703(14) 1 calc R U P . .


_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
Cu O1 1.9849(16) . ?
Cu N1 1.993(2) . ?
Cu N2 1.9387(19) . ?
Cu N3 1.9658(19) 4_656 ?
O1 C4 1.262(3) . ?
O2 C4 1.260(3) . ?
O3 C3 1.266(3) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C1 1.476(3) . ?
N2 C3 1.311(3) . ?
N2 C5 1.451(3) . ?
N3 C8 1.386(3) . ?
N3 C9 1.329(3) . ?
N4 H4 0.8800 . ?
N4 C7 1.386(3) . ?
N4 C9 1.338(3) . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
C1 C2 1.501(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.515(4) . ?
C4 C5 1.524(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.556(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.492(3) . ?
C7 C8 1.369(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
O4 H4A 0.8400 . ?
O4 C10 1.468(7) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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 Cu N1 168.08(10) . . ?
N2 Cu O1 84.06(7) . . ?
N2 Cu N1 94.35(9) . . ?
N2 Cu N3 159.59(9) . 4_656 ?
N3 Cu O1 92.52(7) 4_656 . ?
N3 Cu N1 92.96(9) 4_656 . ?
C4 O1 Cu 113.48(15) . . ?
Cu N1 H1A 109.1 . . ?
Cu N1 H1B 109.1 . . ?
H1A N1 H1B 107.8 . . ?
C1 N1 Cu 112.70(17) . . ?
C1 N1 H1A 109.1 . . ?
C1 N1 H1B 109.1 . . ?
C3 N2 Cu 131.42(18) . . ?
C3 N2 C5 116.8(2) . . ?
C5 N2 Cu 111.40(14) . . ?
C8 N3 Cu 129.51(16) . 4_656 ?
C9 N3 Cu 124.54(15) . 4_656 ?
C9 N3 C8 105.86(18) . . ?
C7 N4 H4 125.9 . . ?
C9 N4 H4 125.9 . . ?
C9 N4 C7 108.13(18) . . ?
N1 C1 H1C 109.1 . . ?
N1 C1 H1D 109.1 . . ?
N1 C1 C2 112.6(3) . . ?
H1C C1 H1D 107.8 . . ?
C2 C1 H1C 109.1 . . ?
C2 C1 H1D 109.1 . . ?
C1 C2 H2A 108.1 . . ?
C1 C2 H2B 108.1 . . ?
C1 C2 C3 116.9(2) . . ?
H2A C2 H2B 107.3 . . ?
C3 C2 H2A 108.1 . . ?
C3 C2 H2B 108.1 . . ?
O3 C3 N2 123.4(3) . . ?
O3 C3 C2 118.0(2) . . ?
N2 C3 C2 118.6(2) . . ?
O1 C4 C5 118.1(2) . . ?
O2 C4 O1 124.0(2) . . ?
O2 C4 C5 117.7(2) . . ?
N2 C5 C4 108.90(18) . . ?
N2 C5 H5 109.7 . . ?
N2 C5 C6 111.8(2) . . ?
C4 C5 H5 109.7 . . ?
C4 C5 C6 107.10(19) . . ?
C6 C5 H5 109.7 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 C5 111.45(18) . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
N4 C7 C6 122.0(2) . . ?
C8 C7 N4 105.42(18) . . ?
C8 C7 C6 132.3(2) . . ?
N3 C8 H8 125.3 . . ?
C7 C8 N3 109.49(19) . . ?
C7 C8 H8 125.3 . . ?
N3 C9 N4 111.10(19) . . ?
N3 C9 H9 124.4 . . ?
N4 C9 H9 124.4 . . ?
C10 O4 H4A 109.5 . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O3 0.91 2.15 2.990(4) 152.9 7_566 yes
N4 H4 O2 0.88 1.83 2.690(3) 167.1 3_566 yes
O4 H4A O3 0.84 1.83 2.655(3) 168.5 7_566 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu O1 C4 O2 178.6(2) . . . . ?
Cu O1 C4 C5 3.6(3) . . . . ?
Cu N1 C1 C2 -64.0(3) . . . . ?
Cu N2 C3 O3 174.2(2) . . . . ?
Cu N2 C3 C2 -4.0(4) . . . . ?
Cu N2 C5 C4 21.5(2) . . . . ?
Cu N2 C5 C6 -96.62(18) . . . . ?
Cu N3 C8 C7 -176.36(16) 4_656 . . . ?
Cu N3 C9 N4 176.85(16) 4_656 . . . ?
O1 C4 C5 N2 -16.8(3) . . . . ?
O1 C4 C5 C6 104.3(3) . . . . ?
O2 C4 C5 N2 167.8(2) . . . . ?
O2 C4 C5 C6 -71.1(3) . . . . ?
N1 C1 C2 C3 65.8(3) . . . . ?
N2 C5 C6 C7 66.4(2) . . . . ?
N4 C7 C8 N3 -0.4(3) . . . . ?
C1 C2 C3 O3 153.5(3) . . . . ?
C1 C2 C3 N2 -28.3(4) . . . . ?
C3 N2 C5 C4 -164.8(2) . . . . ?
C3 N2 C5 C6 77.0(3) . . . . ?
C4 C5 C6 C7 -52.8(2) . . . . ?
C5 N2 C3 O3 2.0(4) . . . . ?
C5 N2 C3 C2 -176.1(2) . . . . ?
C5 C6 C7 N4 95.4(3) . . . . ?
C5 C6 C7 C8 -77.6(3) . . . . ?
C6 C7 C8 N3 173.5(2) . . . . ?
C7 N4 C9 N3 -0.3(3) . . . . ?
C8 N3 C9 N4 0.1(3) . . . . ?
C9 N3 C8 C7 0.2(3) . . . . ?
C9 N4 C7 C6 -174.2(2) . . . . ?
C9 N4 C7 C8 0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.397
_oxdiff_exptl_absorpt_empirical_full_min 0.751
# start Validation Reply Form
_vrf_PLAT609_2_100k              
;
PROBLEM: SQUEEZE or MASK Info missing, given ABIN Record ! Check
RESPONSE: Because of decomposition (loss of methanol solvent) the solvent 
sphere (methanol/water molecules) couldn't be modelled so solvent masking 
was used (P. van der Sluis and A. L. Spek, Acta Cryst. (1990). A46, 194-201)
;
# end Validation Reply Form
_chemical_properties_physical    Moisture-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_1_370
_database_code_depnum_ccdc_archive 'CCDC 2327412'
loop_
_audit_author_name
_audit_author_address
'Dubravka Matkovic-Calogovic'
;University of Zagreb, Faculty of Science
Croatia
;
_audit_update_record             
;
2024-01-22 deposited with the CCDC.	2024-11-19 downloaded from the CCDC.
;
_audit_creation_date             2023-12-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H24 Cu2 N8 O6, (H2 O)'
_chemical_formula_sum            'C18 H26 Cu2 N8 O7'
_chemical_formula_weight         593.57
_chemical_absolute_configuration syn
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      trigonal
_space_group_IT_number           152
_space_group_name_H-M_alt        'P 31 2 1'
_space_group_name_Hall           'P 31 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'y, x, -z'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'

_cell_length_a                   8.3611(10)
_cell_length_b                   8.3611(10)
_cell_length_c                   30.450(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1843.5(5)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    2512
_cell_measurement_temperature    370(1)
_cell_measurement_theta_max      76.7540
_cell_measurement_theta_min      4.3500
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.727
_exptl_absorpt_coefficient_mu    2.618
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.91a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'hexagonal plate'
_exptl_crystal_F_000             912
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 -2 0.0659
1 0 2 0.6501
-1 1 0 0.0669
1 -1 0 0.0635
0 -1 -2 0.0641
0 1 2 0.0650
0 0 1 0.0095
0 0 -1 0.0141

_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0885
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            6498
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.399
_diffrn_reflns_theta_min         6.112
_diffrn_ambient_temperature      370(1)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     90.00 117.00   0.50    0.99    --  106.90-146.00   5.00   54
  2  ω     34.00 102.00   0.50    0.99    --  106.90-125.00-180.00  136
  3  ω   -119.00 -94.00   0.50    0.25    --  -47.29 -77.00-150.00   50
  4  ω   -158.00-101.00   0.50    0.99    --  -86.25 -52.00 -13.00  114
  5  ω   -119.00 -93.00   0.50    0.25    --  -47.29 -77.00   0.00   52
  6  ω     34.00  96.00   0.50    0.99    --  106.90 -77.00 150.00  124
  7  ω     35.00  60.00   0.50    0.99    --  106.90 -57.00-120.00   50
  8  ω     37.00  65.00   0.50    0.99    --  106.90 -57.00-150.00   56
  9  ω     94.00 178.00   0.50    0.99    --  106.90  19.00-150.00  168
 10  ω     36.00 112.00   0.50    0.25    --   47.29  28.00-137.00  152
 11  ω    131.00 174.00   0.50    0.99    --  106.90  57.00 -30.00   86
 12  ω     94.00 119.00   0.50    0.25    --   47.29  77.00  90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.591
_reflns_Friedel_fraction_full    0.918
_reflns_Friedel_fraction_max     0.853
_reflns_number_gt                1410
_reflns_number_total             2367
_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       'CrysAlisPro 1.171.43.91a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 42.53a 64-bit (release 15-04-2022))'
_computing_data_reduction        'CrysAlisPro 1.171.43.91a (Rigaku OD, 2023)'
_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         0.546
_refine_diff_density_min         -0.709
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details 
;
 Flack x determined using 397 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2367
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0752
_refine_ls_restrained_S_all      0.959
_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)+(0.1406P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1967
_refine_ls_wR_factor_ref         0.2266
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2. Restrained distances
 Cu1-N1A \\sim Cu1-N1B
 with sigma of 0.005
 N1A-C1A \\sim N1B-C1B
 with sigma of 0.005
 C2A-C3A \\sim C2B-C3B
 with sigma of 0.005
 C3A-O3A \\sim C3B-O3B
 with sigma of 0.005
 C3A-N2 \\sim C3B-N2
 with sigma of 0.005
3. Restrained planarity
 N2, C3A, O3A, C2A
 with sigma of 0.1
 N2, C3B, O3B, C2B
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
N1A \\sim N1B: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 2A
C1A \\sim C1B: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 2A
C2A \\sim C2B: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 2A
C3A \\sim C3B: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 2A
O3A \\sim O3B: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 2A
5. Others
 Sof(N1B)=Sof(H1BA)=Sof(H1BB)=Sof(C1B)=Sof(H1BC)=Sof(H1BD)=Sof(C2B)=Sof(H2BA)=
 Sof(H2BB)=Sof(C3B)=Sof(O3B)=1-FVAR(1)
 Sof(N1A)=Sof(H1AA)=Sof(H1AB)=Sof(C1A)=Sof(H1AC)=Sof(H1AD)=Sof(C2A)=Sof(H2AA)=
 Sof(H2AB)=Sof(C3A)=Sof(O3A)=FVAR(1)
 Fixed Sof: O1W(0.5)
6.a Ternary CH refined with riding coordinates:
 C5(H5)
6.b Secondary CH2 refined with riding coordinates:
 N1A(H1AA,H1AB), C1A(H1AC,H1AD), C2A(H2AA,H2AB), N1B(H1BA,H1BB), C1B(H1BC,
 H1BD), C2B(H2BA,H2BB), C6(H6A,H6B)
6.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C8(H8), C9(H9)
;
_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 0.8432(2) 0.5284(2) 0.46272(3) 0.1108(7) Uani 1 1 d D . . . .
O1 O 1.0646(14) 0.7602(16) 0.4656(2) 0.133(3) Uani 1 1 d . . . . .
O2 O 1.199(3) 1.030(2) 0.4320(4) 0.227(9) Uani 1 1 d . . . . .
N2 N 0.8754(17) 0.5725(12) 0.4009(2) 0.126(4) Uani 1 1 d D . . . .
N3 N 0.5576(16) 0.7936(18) 0.4747(2) 0.125(3) Uani 1 1 d . . . . .
N4 N 0.528(2) 0.6857(17) 0.4083(3) 0.135(4) Uani 1 1 d . . . . .
H4 H 0.478047 0.622592 0.384918 0.162 Uiso 1 1 calc R U . . .
N1A N 0.670(6) 0.262(2) 0.4621(8) 0.123(8) Uani 0.52(3) 1 d D U P A 1
H1AA H 0.727653 0.199619 0.469177 0.147 Uiso 0.52(3) 1 calc R U P A 1
H1AB H 0.578207 0.231715 0.480936 0.147 Uiso 0.52(3) 1 calc R U P A 1
C1A C 0.599(6) 0.220(7) 0.4155(10) 0.129(10) Uani 0.52(3) 1 d D U P A 1
H1AC H 0.543808 0.294043 0.408094 0.155 Uiso 0.52(3) 1 calc R U P A 1
H1AD H 0.504492 0.090917 0.413342 0.155 Uiso 0.52(3) 1 calc R U P A 1
C2A C 0.757(6) 0.261(3) 0.3816(8) 0.126(11) Uani 0.52(3) 1 d D U P A 1
H2AA H 0.842081 0.226554 0.394559 0.151 Uiso 0.52(3) 1 calc R U P A 1
H2AB H 0.703368 0.184313 0.355743 0.151 Uiso 0.52(3) 1 calc R U P A 1
C3A C 0.861(4) 0.456(3) 0.3682(5) 0.097(7) Uani 0.52(3) 1 d D U P A 1
O3A O 0.917(4) 0.517(3) 0.3306(5) 0.128(8) Uani 0.52(3) 1 d D U P A 1
N1B N 0.653(6) 0.272(3) 0.4511(9) 0.116(8) Uani 0.48(3) 1 d D U P A 2
H1BA H 0.648941 0.204947 0.474211 0.140 Uiso 0.48(3) 1 calc R U P A 2
H1BB H 0.544831 0.268178 0.449877 0.140 Uiso 0.48(3) 1 calc R U P A 2
C1B C 0.668(8) 0.176(7) 0.4105(11) 0.143(13) Uani 0.48(3) 1 d D U P A 2
H1BC H 0.789274 0.188073 0.408672 0.171 Uiso 0.48(3) 1 calc R U P A 2
H1BD H 0.575665 0.045678 0.411092 0.171 Uiso 0.48(3) 1 calc R U P A 2
C2B C 0.636(6) 0.269(4) 0.3729(10) 0.143(12) Uani 0.48(3) 1 d D U P A 2
H2BA H 0.628399 0.200946 0.346369 0.172 Uiso 0.48(3) 1 calc R U P A 2
H2BB H 0.517733 0.261659 0.376883 0.172 Uiso 0.48(3) 1 calc R U P A 2
C3B C 0.778(3) 0.464(3) 0.3664(4) 0.110(8) Uani 0.48(3) 1 d D U P A 2
O3B O 0.797(6) 0.508(4) 0.3268(5) 0.142(10) Uani 0.48(3) 1 d D U P A 2
C4 C 1.099(3) 0.867(2) 0.4318(4) 0.147(5) Uani 1 1 d . . . . .
C5 C 0.977(2) 0.7649(16) 0.3916(3) 0.126(4) Uani 1 1 d . . . . .
H5 H 1.058631 0.783891 0.366645 0.151 Uiso 1 1 calc R U . . .
C6 C 0.857(2) 0.8415(18) 0.3800(3) 0.134(5) Uani 1 1 d . . . . .
H6A H 0.796747 0.788744 0.352175 0.161 Uiso 1 1 calc R U . . .
H6B H 0.933182 0.973836 0.375869 0.161 Uiso 1 1 calc R U . . .
C7 C 0.712(3) 0.8062(19) 0.4133(3) 0.124(4) Uani 1 1 d . . . . .
C8 C 0.725(2) 0.868(2) 0.4555(3) 0.118(4) Uani 1 1 d . . . . .
H8 H 0.835364 0.950038 0.469200 0.141 Uiso 1 1 calc R U . . .
C9 C 0.436(3) 0.679(2) 0.4453(3) 0.145(5) Uani 1 1 d . . . . .
H9 H 0.309425 0.607190 0.449512 0.175 Uiso 1 1 calc R U . . .
O1W O 0.329(4) 0.077(6) 0.5189(6) 0.26(2) Uani 0.5 1 d . . P . .


_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 1.899(12) . ?
Cu1 N2 1.912(6) . ?
Cu1 N3 1.991(7) 4_556 ?
Cu1 N1A 1.960(15) . ?
Cu1 N1B 1.960(16) . ?
O1 C4 1.299(18) . ?
O2 C4 1.189(18) . ?
N2 C3A 1.357(15) . ?
N2 C3B 1.361(15) . ?
N2 C5 1.422(15) . ?
N3 C8 1.348(18) . ?
N3 C9 1.333(17) . ?
N4 H4 0.8600 . ?
N4 C7 1.36(2) . ?
N4 C9 1.350(18) . ?
N1A H1AA 0.8900 . ?
N1A H1AB 0.8900 . ?
N1A C1A 1.51(3) . ?
C1A H1AC 0.9700 . ?
C1A H1AD 0.9700 . ?
C1A C2A 1.57(5) . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C2A C3A 1.47(2) . ?
C3A O3A 1.247(14) . ?
N1B H1BA 0.8900 . ?
N1B H1BB 0.8900 . ?
N1B C1B 1.51(3) . ?
C1B H1BC 0.9700 . ?
C1B H1BD 0.9700 . ?
C1B C2B 1.48(7) . ?
C2B H2BA 0.9700 . ?
C2B H2BB 0.9700 . ?
C2B C3B 1.47(2) . ?
C3B O3B 1.248(14) . ?
C4 C5 1.55(2) . ?
C5 H5 0.9800 . ?
C5 C6 1.482(19) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.489(19) . ?
C7 C8 1.368(12) . ?
C8 H8 0.9300 . ?
C9 H9 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 N2 83.0(4) . . ?
O1 Cu1 N3 89.2(4) . 4_556 ?
O1 Cu1 N1A 161.8(17) . . ?
O1 Cu1 N1B 165.7(16) . . ?
N2 Cu1 N3 159.6(4) . 4_556 ?
N2 Cu1 N1A 99.4(8) . . ?
N2 Cu1 N1B 89.5(9) . . ?
N1A Cu1 N3 93.9(10) . 4_556 ?
N1B Cu1 N3 101.7(11) . 4_556 ?
C4 O1 Cu1 115.6(10) . . ?
C3A N2 Cu1 129.1(9) . . ?
C3A N2 C5 117.2(10) . . ?
C3B N2 Cu1 130.6(10) . . ?
C3B N2 C5 115.0(11) . . ?
C5 N2 Cu1 111.1(6) . . ?
C8 N3 Cu1 121.8(7) . 4_556 ?
C9 N3 Cu1 131.6(11) . 4_556 ?
C9 N3 C8 106.3(10) . . ?
C7 N4 H4 124.8 . . ?
C9 N4 H4 124.8 . . ?
C9 N4 C7 110.3(10) . . ?
Cu1 N1A H1AA 110.8 . . ?
Cu1 N1A H1AB 110.8 . . ?
H1AA N1A H1AB 108.9 . . ?
C1A N1A Cu1 105(2) . . ?
C1A N1A H1AA 110.8 . . ?
C1A N1A H1AB 110.8 . . ?
N1A C1A H1AC 109.2 . . ?
N1A C1A H1AD 109.2 . . ?
N1A C1A C2A 112(4) . . ?
H1AC C1A H1AD 107.9 . . ?
C2A C1A H1AC 109.2 . . ?
C2A C1A H1AD 109.2 . . ?
C1A C2A H2AA 109.0 . . ?
C1A C2A H2AB 109.0 . . ?
H2AA C2A H2AB 107.8 . . ?
C3A C2A C1A 113(2) . . ?
C3A C2A H2AA 109.0 . . ?
C3A C2A H2AB 109.0 . . ?
N2 C3A C2A 112.7(14) . . ?
O3A C3A N2 119.7(17) . . ?
O3A C3A C2A 127.1(17) . . ?
Cu1 N1B H1BA 107.5 . . ?
Cu1 N1B H1BB 107.5 . . ?
H1BA N1B H1BB 107.0 . . ?
C1B N1B Cu1 119(3) . . ?
C1B N1B H1BA 107.5 . . ?
C1B N1B H1BB 107.5 . . ?
N1B C1B H1BC 110.6 . . ?
N1B C1B H1BD 110.6 . . ?
H1BC C1B H1BD 108.7 . . ?
C2B C1B N1B 106(4) . . ?
C2B C1B H1BC 110.6 . . ?
C2B C1B H1BD 110.6 . . ?
C1B C2B H2BA 108.4 . . ?
C1B C2B H2BB 108.4 . . ?
H2BA C2B H2BB 107.5 . . ?
C3B C2B C1B 115(3) . . ?
C3B C2B H2BA 108.4 . . ?
C3B C2B H2BB 108.4 . . ?
N2 C3B C2B 121.2(18) . . ?
O3B C3B N2 127(2) . . ?
O3B C3B C2B 112(2) . . ?
O1 C4 C5 112.9(13) . . ?
O2 C4 O1 124.7(14) . . ?
O2 C4 C5 122.0(15) . . ?
N2 C5 C4 109.0(10) . . ?
N2 C5 H5 108.1 . . ?
N2 C5 C6 112.7(12) . . ?
C4 C5 H5 108.1 . . ?
C6 C5 C4 110.7(11) . . ?
C6 C5 H5 108.1 . . ?
C5 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
C5 C6 C7 114.2(9) . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
N4 C7 C6 125.1(10) . . ?
N4 C7 C8 103.3(13) . . ?
C8 C7 C6 131.4(16) . . ?
N3 C8 C7 111.5(13) . . ?
N3 C8 H8 124.2 . . ?
C7 C8 H8 124.2 . . ?
N3 C9 N4 108.5(15) . . ?
N3 C9 H9 125.8 . . ?
N4 C9 H9 125.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4 O3A 0.86 1.80 2.65(2) 171.6 5_565 yes
N4 H4 O3B 0.86 1.96 2.78(3) 158.7 5_565 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C4 O2 158.8(19) . . . . ?
Cu1 O1 C4 C5 -13.7(17) . . . . ?
Cu1 N2 C3A C2A 19(2) . . . . ?
Cu1 N2 C3A O3A -167.9(16) . . . . ?
Cu1 N2 C3B C2B -9(3) . . . . ?
Cu1 N2 C3B O3B 173(2) . . . . ?
Cu1 N2 C5 C4 25.3(13) . . . . ?
Cu1 N2 C5 C6 -98.0(9) . . . . ?
Cu1 N3 C8 C7 176.5(9) 4_556 . . . ?
Cu1 N3 C9 N4 -174.8(10) 4_556 . . . ?
Cu1 N1A C1A C2A 64(4) . . . . ?
Cu1 N1B C1B C2B -69(5) . . . . ?
O1 C4 C5 N2 -7.9(18) . . . . ?
O1 C4 C5 C6 116.5(13) . . . . ?
O2 C4 C5 N2 179.3(19) . . . . ?
O2 C4 C5 C6 -56(2) . . . . ?
N2 Cu1 O1 C4 23.1(11) . . . . ?
N2 C5 C6 C7 54.9(13) . . . . ?
N3 Cu1 O1 C4 -138.0(10) 4_556 . . . ?
N4 C7 C8 N3 -2.1(15) . . . . ?
N1A Cu1 O1 C4 122(3) . . . . ?
N1A C1A C2A C3A -84(4) . . . . ?
C1A C2A C3A N2 33(3) . . . . ?
C1A C2A C3A O3A -140(3) . . . . ?
C3A N2 C5 C4 -138.0(16) . . . . ?
C3A N2 C5 C6 98.7(15) . . . . ?
N1B Cu1 O1 C4 82(4) . . . . ?
N1B C1B C2B C3B 66(5) . . . . ?
C1B C2B C3B N2 -29(4) . . . . ?
C1B C2B C3B O3B 148(3) . . . . ?
C3B N2 C5 C4 -172.8(16) . . . . ?
C3B N2 C5 C6 63.9(16) . . . . ?
C4 C5 C6 C7 -67.4(15) . . . . ?
C5 N2 C3A C2A 178(2) . . . . ?
C5 N2 C3A O3A -8(2) . . . . ?
C5 N2 C3B C2B -167(2) . . . . ?
C5 N2 C3B O3B 16(3) . . . . ?
C5 C6 C7 N4 -108.0(15) . . . . ?
C5 C6 C7 C8 66.1(18) . . . . ?
C6 C7 C8 N3 -177.1(13) . . . . ?
C7 N4 C9 N3 -0.3(18) . . . . ?
C8 N3 C9 N4 -0.9(17) . . . . ?
C9 N3 C8 C7 1.9(16) . . . . ?
C9 N4 C7 C6 176.9(14) . . . . ?
C9 N4 C7 C8 1.4(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
# start Validation Reply Form
_vrf_PLAT341_1_370               
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01825 Ang.
RESPONSE:Low bond precision is caused by data collection at 370 K.
;
_vrf_PLAT430_1_370               
;
PROBLEM: Short Inter D...A Contact O1W ..O2 . 2.81 Ang.
RESPONSE: Data were collected at 370 K. This water atom has an occupancy of 0.5 
and the hydrogen atoms were not found nor could be modeled. This is an 
acceptable length of a hydrogen bond.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_170k
_database_code_depnum_ccdc_archive 'CCDC 2327416'
loop_
_audit_author_name
_audit_author_address
'Dubravka Matkovic-Calogovic'
;University of Zagreb, Faculty of Science
Croatia
;
_audit_update_record             
;
2024-01-22 deposited with the CCDC.	2024-11-19 downloaded from the CCDC.
;
_audit_creation_date             2024-01-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H24 Cu2 N8 O6, 2(H2 O)'
_chemical_formula_sum            'C18 H28 Cu2 N8 O8'
_chemical_formula_weight         ?
_chemical_absolute_configuration syn
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           23
_space_group_name_H-M_alt        'I 2 2 2'
_space_group_name_Hall           'I 2 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z'
'x, -y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'

_cell_length_a                   12.09436(16)
_cell_length_b                   13.9509(2)
_cell_length_c                   20.3839(3)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_volume                     3439.30(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8572
_cell_measurement_temperature    170(1)
_cell_measurement_theta_max      75.6690
_cell_measurement_theta_min      3.8620
_cell_oxdiff_angle_alpha         89.9988(11)
_cell_oxdiff_angle_beta          89.9698(11)
_cell_oxdiff_angle_gamma         89.9945(14)
_cell_oxdiff_length_a            12.0923(2)
_cell_oxdiff_length_b            13.9548(3)
_cell_oxdiff_length_c            20.38161(17)
_cell_oxdiff_measurement_reflns_used 8572
_cell_oxdiff_volume              3439.30(9)
_shelx_estimated_absorpt_T_max   0.835
_shelx_estimated_absorpt_T_min   0.757
_exptl_absorpt_coefficient_mu    ?
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.91a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 13 0.0769
0 0 -13 0.0705
0 9 0 0.0753
0 -9 0 0.0775
-8 0 0 0.0475
8 0 0 0.0486

_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.098

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10171
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.368
_diffrn_reflns_theta_min         4.251
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      170(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  65.00   0.50    0.80    --  106.90 -99.00 -60.00   60
  2  ω     72.00  98.00   0.50    0.80    --  106.90 -99.00 -60.00   52
  3  ω    -30.00  25.00   0.50    0.40    --  -47.16  35.00-167.00  110
  4  ω    -39.00 -14.00   0.50    0.80    --  -86.25  35.00-167.00   50
  5  ω    -61.00 -35.00   0.50    0.80    --  -86.25  57.00-120.00   52
  6  ω    -40.00 -13.00   0.50    0.80    --  -86.25  38.00   0.00   54
  7  ω    -25.00  28.00   0.50    0.40    --  -47.16  19.00 -30.00  106
  8  ω   -120.00 -35.00   0.50    0.40    --  -47.16 -35.00  35.00  170
  9  ω   -120.00 -95.00   0.50    0.80    --  -86.25-111.00-177.00   50
 10  ω   -119.00 -92.00   0.50    0.40    --  -47.16-125.00  90.00   54
 11  ω     39.00  65.00   0.50    0.80    --  106.90 -57.00 -60.00   52
 12  ω     38.00  66.00   0.50    0.80    --  106.90 -57.00   0.00   56
 13  ω     35.00  60.00   0.50    0.80    --  106.90 -57.00-150.00   50
 14  ω     38.00  66.00   0.50    0.80    --  106.90 -57.00 -90.00   56
 15  ω     35.00  60.00   0.50    0.80    --  106.90 -57.00 -30.00   50
 16  ω     38.00  63.00   0.50    0.80    --  106.90 -57.00  30.00   50
 17  ω     37.00  63.00   0.50    0.80    --  106.90 -57.00 150.00   52
 18  ω     41.00  66.00   0.50    0.80    --  106.90 -57.00-180.00   50
 19  ω     99.00 174.00   0.50    0.80    --  106.90  35.00-167.00  150
 20  ω    140.00 166.00   0.50    0.80    --  106.90  19.00-180.00   52
 21  ω     94.00 130.00   0.50    0.80    --  106.90  19.00-180.00   72
 22  ω     96.00 169.00   0.50    0.80    --  106.90  19.00 -30.00  146
 23  ω    138.00 177.00   0.50    0.80    --  106.90  92.00  20.00   78
 24  ω    142.00 176.00   0.50    0.80    --  106.90 125.00  30.00   68
 25  ω    100.00 130.00   0.50    0.80    --  106.90 125.00  30.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0819105000
_diffrn_orient_matrix_UB_12      -0.0820513000
_diffrn_orient_matrix_UB_13      0.0139773000
_diffrn_orient_matrix_UB_21      0.0941205000
_diffrn_orient_matrix_UB_22      0.0593775000
_diffrn_orient_matrix_UB_23      -0.0307188000
_diffrn_orient_matrix_UB_31      0.0257464000
_diffrn_orient_matrix_UB_32      0.0439237000
_diffrn_orient_matrix_UB_33      0.0676330000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.913
_reflns_number_gt                3408
_reflns_number_total             3440
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro 1.171.43.91a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 42.53a 64-bit (release 15-04-2022))'
_computing_data_reduction        'CrysAlisPro 1.171.43.91a (Rigaku OD, 2023)'
_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         0.603
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1452 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.026(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3440
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.042
_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)+(0.0552P)²+2.0329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0818
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 OW1(HW1A,HW1B)
2.b Ternary CH refined with riding coordinates:
 C5(H5)
2.c Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C1(H1C,H1D), C2(H2A,H2B), C6(H6A,H6B)
2.d Aromatic/amide H refined with riding coordinates:
 N4(H4), C8(H8), C9(H9)
;
_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 0.40689(3) 0.34286(3) 0.67622(2) 0.03036(13) Uani 1 1 d . . . . .
O1 O 0.34702(15) 0.35263(15) 0.58592(9) 0.0320(4) Uani 1 1 d . . . . .
O2 O 0.19131(17) 0.3845(2) 0.53182(11) 0.0462(6) Uani 1 1 d . . . . .
O3 O 0.1044(2) 0.36498(19) 0.76955(13) 0.0526(6) Uani 1 1 d . . . . .
N1 N 0.4587(2) 0.3032(2) 0.76484(13) 0.0429(6) Uani 1 1 d . . . . .
H1A H 0.519475 0.265338 0.760402 0.051 Uiso 1 1 calc R U . . .
H1B H 0.478976 0.356292 0.787798 0.051 Uiso 1 1 calc R U . . .
N2 N 0.25297(19) 0.35669(18) 0.70208(11) 0.0317(5) Uani 1 1 d . . . . .
N4 N 0.30387(19) 0.59219(18) 0.58228(11) 0.0312(5) Uani 1 1 d . . . . .
H4 H 0.262962 0.591358 0.546580 0.037 Uiso 1 1 calc R U . . .
N3 N 0.4433(2) 0.62030(17) 0.64760(11) 0.0302(4) Uani 1 1 d . . . . .
C1 C 0.3734(3) 0.2504(3) 0.80263(18) 0.0498(8) Uani 1 1 d . . . . .
H1C H 0.405649 0.227653 0.844472 0.060 Uiso 1 1 calc R U . . .
H1D H 0.349260 0.193517 0.777308 0.060 Uiso 1 1 calc R U . . .
C2 C 0.2742(3) 0.3134(3) 0.81693(16) 0.0493(8) Uani 1 1 d . . . . .
H2A H 0.300848 0.370927 0.840580 0.059 Uiso 1 1 calc R U . . .
H2B H 0.225029 0.278051 0.847306 0.059 Uiso 1 1 calc R U . . .
C3 C 0.2049(3) 0.3470(2) 0.75936(15) 0.0400(6) Uani 1 1 d . . . . .
C4 C 0.2441(2) 0.3723(2) 0.58373(14) 0.0322(6) Uani 1 1 d . . . . .
C5 C 0.1857(2) 0.3922(2) 0.64799(14) 0.0304(5) Uani 1 1 d . . . . .
H5 H 0.112467 0.358960 0.648253 0.037 Uiso 1 1 calc R U . A 2
C6 C 0.1676(2) 0.5020(2) 0.65314(15) 0.0336(6) Uani 1 1 d . . . . .
H6A H 0.112778 0.522334 0.619875 0.040 Uiso 1 1 calc R U . . .
H6B H 0.137466 0.517671 0.697007 0.040 Uiso 1 1 calc R U . . .
C7 C 0.2736(2) 0.5560(2) 0.64273(13) 0.0296(5) Uani 1 1 d . . . . .
C8 C 0.3614(2) 0.57423(19) 0.68273(14) 0.0303(5) Uani 1 1 d . . . . .
H8 H 0.365561 0.557778 0.727881 0.036 Uiso 1 1 calc R U . . .
C9 C 0.4050(2) 0.6285(2) 0.58706(14) 0.0328(5) Uani 1 1 d . . . . .
H9 H 0.444696 0.656533 0.551714 0.039 Uiso 1 1 calc R U . . .
OW1 O 0.4521(3) 0.1730(2) 0.63935(17) 0.0705(9) Uani 1 1 d G . . . .
HW1A H 0.520749 0.154592 0.640580 0.106 Uiso 1 1 d G U . . .
HW1B H 0.440233 0.187047 0.598392 0.106 Uiso 1 1 d G 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 1.9827(19) . ?
Cu1 N1 1.990(3) . ?
Cu1 N2 1.944(2) . ?
Cu1 N3 1.972(2) 2_665 ?
O1 C4 1.276(3) . ?
O2 C4 1.247(4) . ?
O3 C3 1.258(4) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C1 1.484(4) . ?
N2 C3 1.311(4) . ?
N2 C5 1.457(4) . ?
N4 H4 0.8800 . ?
N4 C7 1.381(3) . ?
N4 C9 1.328(4) . ?
N3 C8 1.381(4) . ?
N3 C9 1.323(4) . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
C1 C2 1.516(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.516(5) . ?
C4 C5 1.514(4) . ?
C5 H5 1.0000 . ?
C5 C6 1.551(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.502(4) . ?
C7 C8 1.362(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
OW1 HW1A 0.8700 . ?
OW1 HW1B 0.8693 . ?

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 N1 167.58(11) . . ?
N2 Cu1 O1 83.99(9) . . ?
N2 Cu1 N1 94.74(11) . . ?
N2 Cu1 N3 159.09(10) . 2_665 ?
N3 Cu1 O1 92.46(9) 2_665 . ?
N3 Cu1 N1 92.98(11) 2_665 . ?
C4 O1 Cu1 113.81(18) . . ?
Cu1 N1 H1A 109.0 . . ?
Cu1 N1 H1B 109.0 . . ?
H1A N1 H1B 107.8 . . ?
C1 N1 Cu1 113.0(2) . . ?
C1 N1 H1A 109.0 . . ?
C1 N1 H1B 109.0 . . ?
C3 N2 Cu1 131.0(2) . . ?
C3 N2 C5 117.5(3) . . ?
C5 N2 Cu1 111.30(17) . . ?
C7 N4 H4 125.7 . . ?
C9 N4 H4 125.7 . . ?
C9 N4 C7 108.5(2) . . ?
C8 N3 Cu1 128.84(19) . 2_665 ?
C9 N3 Cu1 125.10(19) . 2_665 ?
C9 N3 C8 105.8(2) . . ?
N1 C1 H1C 109.4 . . ?
N1 C1 H1D 109.4 . . ?
N1 C1 C2 111.2(3) . . ?
H1C C1 H1D 108.0 . . ?
C2 C1 H1C 109.4 . . ?
C2 C1 H1D 109.4 . . ?
C1 C2 H2A 107.8 . . ?
C1 C2 H2B 107.8 . . ?
C1 C2 C3 117.9(3) . . ?
H2A C2 H2B 107.2 . . ?
C3 C2 H2A 107.8 . . ?
C3 C2 H2B 107.8 . . ?
O3 C3 N2 123.7(3) . . ?
O3 C3 C2 117.9(3) . . ?
N2 C3 C2 118.4(3) . . ?
O1 C4 C5 117.7(3) . . ?
O2 C4 O1 123.9(3) . . ?
O2 C4 C5 118.1(2) . . ?
N2 C5 C4 109.4(2) . . ?
N2 C5 H5 109.4 . . ?
N2 C5 C6 111.3(2) . . ?
C4 C5 H5 109.4 . . ?
C4 C5 C6 107.8(2) . . ?
C6 C5 H5 109.4 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 C5 111.4(2) . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
N4 C7 C6 122.4(2) . . ?
C8 C7 N4 105.0(2) . . ?
C8 C7 C6 132.4(3) . . ?
N3 C8 H8 125.2 . . ?
C7 C8 N3 109.6(2) . . ?
C7 C8 H8 125.2 . . ?
N4 C9 H9 124.5 . . ?
N3 C9 N4 111.0(2) . . ?
N3 C9 H9 124.5 . . ?
HW1A OW1 HW1B 104.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4 O2 0.88 1.85 2.714(3) 167.4 4_566 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C4 O2 177.7(2) . . . . ?
Cu1 O1 C4 C5 4.3(3) . . . . ?
Cu1 N1 C1 C2 -63.9(4) . . . . ?
Cu1 N2 C3 O3 174.8(2) . . . . ?
Cu1 N2 C3 C2 -4.5(5) . . . . ?
Cu1 N2 C5 C4 21.1(3) . . . . ?
Cu1 N2 C5 C6 -97.9(2) . . . . ?
Cu1 N3 C8 C7 -175.3(2) 2_665 . . . ?
Cu1 N3 C9 N4 176.08(19) 2_665 . . . ?
O1 C4 C5 N2 -17.0(3) . . . . ?
O1 C4 C5 C6 104.2(3) . . . . ?
O2 C4 C5 N2 169.2(3) . . . . ?
O2 C4 C5 C6 -69.6(3) . . . . ?
N1 C1 C2 C3 65.6(4) . . . . ?
N2 C5 C6 C7 67.5(3) . . . . ?
N4 C7 C8 N3 -0.1(3) . . . . ?
C1 C2 C3 O3 152.5(3) . . . . ?
C1 C2 C3 N2 -28.2(5) . . . . ?
C3 N2 C5 C4 -164.2(3) . . . . ?
C3 N2 C5 C6 76.8(3) . . . . ?
C4 C5 C6 C7 -52.5(3) . . . . ?
C5 N2 C3 O3 1.4(5) . . . . ?
C5 N2 C3 C2 -177.9(3) . . . . ?
C5 C6 C7 N4 94.9(3) . . . . ?
C5 C6 C7 C8 -79.0(4) . . . . ?
C6 C7 C8 N3 174.6(3) . . . . ?
C7 N4 C9 N3 -1.3(3) . . . . ?
C8 N3 C9 N4 1.2(3) . . . . ?
C9 N4 C7 C6 -174.6(3) . . . . ?
C9 N4 C7 C8 0.8(3) . . . . ?
C9 N3 C8 C7 -0.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.502
_oxdiff_exptl_absorpt_empirical_full_min 0.739
# start Validation Reply Form
_vrf_PLAT609_2_170k              
;
PROBLEM: SQUEEZE or MASK Info missing, given ABIN Record ! Check
RESPONSE: Because of decomposition (loss of methanol solvent) the solvent 
sphere (methanol/water molecules) couldn't be modelled so solvent masking 
was used (P. van der Sluis and A. L. Spek, Acta Cryst. (1990). A46, 194-201)
;
# end Validation Reply Form
_chemical_properties_physical    Moisture-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 2327429'
loop_
_audit_author_name
_audit_author_address
'Dubravka Matkovic-Calogovic'
;University of Zagreb, Faculty of Science
Croatia
;
_audit_update_record             
;
2024-01-22 deposited with the CCDC.	2024-11-19 downloaded from the CCDC.
;
_audit_creation_date             2024-01-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H32 Cu2 N8 O8, 5.5(C H4 O)'
_chemical_formula_sum            'C25.50 H54 Cu2 N8 O13.50'
_chemical_formula_weight         ?
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         ?
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      trigonal
_space_group_IT_number           152
_space_group_name_H-M_alt        'P 31 2 1'
_space_group_name_Hall           'P 31 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'y, x, -z'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'

_cell_length_a                   13.3717(9)
_cell_length_b                   13.3717(9)
_cell_length_c                   36.410(2)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                120.0
_cell_volume                     5637.9(6)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    1629
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      20.6940
_cell_measurement_theta_min      4.5220
_cell_oxdiff_angle_alpha         90.037(9)
_cell_oxdiff_angle_beta          89.850(9)
_cell_oxdiff_angle_gamma         120.009(15)
_cell_oxdiff_length_a            13.371(2)
_cell_oxdiff_length_b            13.3691(17)
_cell_oxdiff_length_c            36.421(3)
_cell_oxdiff_measurement_reflns_used 1629
_cell_oxdiff_volume              5638(1)
_shelx_estimated_absorpt_T_max   0.795
_shelx_estimated_absorpt_T_min   0.620
_exptl_absorpt_coefficient_mu    1.201
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2574
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0960
_diffrn_reflns_av_unetI/netI     0.1435
_diffrn_reflns_Laue_measured_fraction_full 0.859
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            13784
_diffrn_reflns_point_group_measured_fraction_full 0.825
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_theta_full        24.880
_diffrn_reflns_theta_max         24.880
_diffrn_reflns_theta_min         4.295
_diffrn_ambient_temperature      150(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.859
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -57.00  60.00   1.00    1.00    --  -18.46  37.00  30.00  117
  2  ω    -45.00  59.00   1.00    1.00    --  -18.46 -19.00-120.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0382212000
_diffrn_orient_matrix_UB_12      -0.0110925000
_diffrn_orient_matrix_UB_13      -0.0104625000
_diffrn_orient_matrix_UB_21      0.0326825000
_diffrn_orient_matrix_UB_22      0.0062597000
_diffrn_orient_matrix_UB_23      0.0160208000
_diffrn_orient_matrix_UB_31      -0.0349846000
_diffrn_orient_matrix_UB_32      -0.0599301000
_diffrn_orient_matrix_UB_33      0.0036249000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.688
_reflns_Friedel_fraction_full    0.780
_reflns_Friedel_fraction_max     0.780
_reflns_number_gt                9993
_reflns_number_total             13784
_reflns_odcompleteness_completeness 98.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     21.92
_reflns_special_details          
;
 _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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         1.111
_refine_diff_density_min         -1.020
_refine_diff_density_rms         0.155
_refine_ls_abs_structure_details 
;
 Flack x determined using 918 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.022(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         13784
_refine_ls_number_restraints     49
_refine_ls_R_factor_all          0.1463
_refine_ls_R_factor_gt           0.1068
_refine_ls_restrained_S_all      1.062
_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)+84.9862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1967
_refine_ls_wR_factor_ref         0.2223
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O2-H2
 0.85 with sigma of 0.01
 O1-H1
 0.85 with sigma of 0.01
 O3-C3
 1.4 with sigma of 0.01
 O4-C4
 1.4 with sigma of 0.01
 O5-C5
 1.4 with sigma of 0.01
 O8-C8
 1.4 with sigma of 0.01
 O6-C6
 1.4 with sigma of 0.01
 O7-C7
 1.4 with sigma of 0.01
 O2-C2
 1.4 with sigma of 0.01
 O1-C1
 1.4 with sigma of 0.01
 Cu1-H1
 3.03 with sigma of 0.02
 Cu2-H2
 3.03 with sigma of 0.02
 C1-H1
 1.877 with sigma of 0.02
 C2-H2
 1.877 with sigma of 0.02
3. Rigid bond restraints
 Cu1, O1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 Cu1, N12
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 Cu1, N11
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.02
 Cu1, N23
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.02
 Cu1, O11
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
Cu1 \\sim O1: within 2.4A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2.4A
Cu1 \\sim N12: within 2.1A with sigma of 0.01 and sigma for terminal atoms of
0.04 within 2.1A
Cu1 \\sim N11: within 2.1A with sigma of 0.002 and sigma for terminal atoms of
0.04 within 2.1A
Cu1 \\sim N23: within 2.1A with sigma of 0.005 and sigma for terminal atoms of
0.04 within 2.1A
Cu1 \\sim O11: within 2.1A with sigma of 0.01 and sigma for terminal atoms of
0.04 within 2.1A
5. Others
 Fixed Sof: O6(0.5) H6(0.5) C6(0.5) H6A(0.5) H6B(0.5) H6C(0.5)
 Fixed X: H6A(0.678901) H6B(0.73812) H6C(0.60323)
 Fixed Y: H6A(0.68976) H6B(0.767281) H6C(0.691251)
 Fixed Z: H6A(-0.02174) H6B(0.01275) H6C(0.01091)
6.a Ternary CH refined with riding coordinates:
 C15(H15), C25(H25)
6.b Secondary CH2 refined with riding coordinates:
 N11(H11A,H11B), N21(H21A,H21B), C11(H11C,H11D), C12(H12A,H12B), C16(H16A,
 H16B), C21(H21C,H21D), C22(H22A,H22B), C26(H26A,H26B)
6.c Me refined with riding coordinates:
 C1(H1A,H1B,H1C)
6.d Aromatic/amide H refined with riding coordinates:
 N14(H14), N24(H24), C18(H18), C19(H19), C28(H28), C29(H29)
6.e Tetrahedral OH refined with riding coordinates:
 O5(H5), O8(H8), O6(H6)
6.f Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C7(H7A,
 H7B,H7C), C8(H8A,H8B,H8C)
6.g Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4), O7(H7)
;
_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 1.3288(2) 0.2008(2) 0.14159(6) 0.0312(7) Uani 1 1 d D U . . .
Cu2 Cu 1.1987(2) 0.4471(2) 0.08580(7) 0.0333(7) Uani 1 1 d D . . . .
O1 O 1.3088(13) 0.0133(12) 0.1363(4) 0.040(4) Uani 1 1 d D U . . .
H1 H 1.336(9) -0.009(4) 0.119(3) 0.060 Uiso 1 1 d D U . . .
O2 O 1.1697(12) 0.6050(12) 0.1010(4) 0.046(4) Uani 1 1 d D . . . .
H2 H 1.221(6) 0.677(3) 0.102(5) 0.070 Uiso 1 1 d D U . . .
O11 O 1.2249(11) 0.1475(11) 0.1841(3) 0.028(3) Uani 1 1 d . U . . .
O12 O 1.2163(11) 0.1744(12) 0.2440(4) 0.037(4) Uani 1 1 d . . . . .
O13 O 1.6215(11) 0.3729(12) 0.2068(3) 0.033(4) Uani 1 1 d . . . . .
O21 O 1.0327(12) 0.3481(12) 0.0960(3) 0.031(4) Uani 1 1 d . . . . .
O22 O 0.8647(11) 0.2257(12) 0.0685(3) 0.034(4) Uani 1 1 d . . . . .
O23 O 1.1716(12) 0.3951(12) -0.0264(3) 0.034(4) Uani 1 1 d . . . . .
N11 N 1.4505(13) 0.2637(14) 0.1015(4) 0.025(2) Uani 1 1 d . U . . .
H11A H 1.420211 0.226313 0.079903 0.030 Uiso 1 1 calc R U . . .
H11B H 1.477580 0.340429 0.098095 0.030 Uiso 1 1 calc R U . . .
N12 N 1.4464(14) 0.2756(13) 0.1794(4) 0.026(4) Uani 1 1 d . U . . .
N13 N 1.2381(14) 0.4329(15) 0.1364(4) 0.033(5) Uani 1 1 d . . . . .
N14 N 1.2189(14) 0.3950(13) 0.1960(4) 0.025(4) Uani 1 1 d . . . . .
H14 H 1.186429 0.376383 0.217838 0.030 Uiso 1 1 calc R U . . .
N21 N 1.3584(15) 0.5704(16) 0.0732(4) 0.040(5) Uani 1 1 d . . . . .
H21A H 1.383842 0.627387 0.090402 0.048 Uiso 1 1 calc R U . . .
H21B H 1.406314 0.540467 0.073518 0.048 Uiso 1 1 calc R U . . .
N22 N 1.1543(13) 0.4041(15) 0.0352(4) 0.030(4) Uani 1 1 d . . . . .
N23 N 1.2005(14) 0.1627(14) 0.1077(4) 0.028(3) Uani 1 1 d . U . . .
N24 N 1.0211(15) 0.0948(14) 0.0893(4) 0.033(4) Uani 1 1 d . . . . .
H24 H 0.945155 0.056610 0.089443 0.040 Uiso 1 1 calc R U . . .
C1 C 1.2046(19) -0.084(2) 0.1474(6) 0.059(8) Uiso 1 1 d D . . . .
H1A H 1.209360 -0.153920 0.143616 0.088 Uiso 1 1 calc R U . . .
H1B H 1.191307 -0.076643 0.173521 0.088 Uiso 1 1 calc R U . . .
H1C H 1.140578 -0.088668 0.132931 0.088 Uiso 1 1 calc R U . . .
C2 C 1.072(2) 0.593(3) 0.1192(7) 0.083(10) Uiso 1 1 d D . . . .
H2A H 1.004885 0.555308 0.102938 0.124 Uiso 1 1 calc R U . . .
H2B H 1.085265 0.670081 0.125918 0.124 Uiso 1 1 calc R U . . .
H2C H 1.058070 0.547008 0.141429 0.124 Uiso 1 1 calc R U . . .
C11 C 1.5449(19) 0.244(2) 0.1138(5) 0.041(6) Uiso 1 1 d . . . . .
H11C H 1.592245 0.247480 0.092426 0.049 Uiso 1 1 calc R U . . .
H11D H 1.511269 0.165678 0.124710 0.049 Uiso 1 1 calc R U . . .
C12 C 1.6230(19) 0.3352(18) 0.1427(5) 0.034(6) Uiso 1 1 d . . . . .
H12A H 1.690711 0.325846 0.147603 0.041 Uiso 1 1 calc R U . . .
H12B H 1.651934 0.413108 0.132124 0.041 Uiso 1 1 calc R U . . .
C13 C 1.5634(19) 0.3281(19) 0.1789(5) 0.031(5) Uiso 1 1 d . . . . .
C14 C 1.2649(18) 0.1898(17) 0.2144(5) 0.023(5) Uiso 1 1 d . . . . .
C15 C 1.3927(18) 0.2844(18) 0.2134(5) 0.031(5) Uiso 1 1 d . . . . .
H15 H 1.433429 0.274231 0.234843 0.038 Uiso 1 1 calc R U . . .
C16 C 1.4027(18) 0.4035(17) 0.2158(5) 0.033(6) Uiso 1 1 d . . . . .
H16A H 1.377206 0.413109 0.240410 0.040 Uiso 1 1 calc R U . . .
H16B H 1.484565 0.464027 0.212715 0.040 Uiso 1 1 calc R U . . .
C17 C 1.3312(19) 0.4186(18) 0.1871(5) 0.031(5) Uiso 1 1 d . . . . .
C18 C 1.3420(18) 0.4410(16) 0.1503(5) 0.024(5) Uiso 1 1 d . . . . .
H18 H 1.408567 0.459304 0.136077 0.029 Uiso 1 1 calc R U . . .
C19 C 1.169(2) 0.4064(18) 0.1646(5) 0.036(6) Uiso 1 1 d . . . . .
H19 H 1.093920 0.396048 0.163422 0.044 Uiso 1 1 calc R U . . .
C21 C 1.3624(19) 0.6207(18) 0.0359(5) 0.036(6) Uiso 1 1 d . . . . .
H21C H 1.308994 0.651874 0.035515 0.043 Uiso 1 1 calc R U . . .
H21D H 1.441363 0.685628 0.031282 0.043 Uiso 1 1 calc R U . . .
C22 C 1.3298(18) 0.5337(18) 0.0059(5) 0.036(6) Uiso 1 1 d . . . . .
H22A H 1.345980 0.574962 -0.017821 0.043 Uiso 1 1 calc R U . . .
H22B H 1.381389 0.500653 0.007606 0.043 Uiso 1 1 calc R U . . .
C23 C 1.2095(18) 0.4369(18) 0.0050(5) 0.026(5) Uiso 1 1 d . . . . .
C24 C 0.972(2) 0.2936(19) 0.0677(6) 0.034(6) Uiso 1 1 d . . . . .
C25 C 1.0380(18) 0.3027(18) 0.0335(5) 0.026(5) Uiso 1 1 d . . . . .
H25 H 0.996366 0.312660 0.012255 0.031 Uiso 1 1 calc R U . . .
C26 C 1.0399(19) 0.1890(19) 0.0279(5) 0.038(6) Uiso 1 1 d . . . . .
H26A H 0.960522 0.125121 0.023107 0.045 Uiso 1 1 calc R U . . .
H26B H 1.087952 0.196611 0.006207 0.045 Uiso 1 1 calc R U . . .
C27 C 1.0886(17) 0.1603(18) 0.0617(5) 0.026(5) Uiso 1 1 d . . . . .
C28 C 1.198(2) 0.1970(19) 0.0726(5) 0.036(6) Uiso 1 1 d . . . . .
H28 H 1.264444 0.240876 0.057807 0.043 Uiso 1 1 calc R U . . .
C29 C 1.0877(19) 0.0976(18) 0.1160(6) 0.035(5) Uiso 1 1 d . . . . .
H29 H 1.059742 0.058144 0.138656 0.042 Uiso 1 1 calc R U . . .
O3 O 0.982(2) 0.337(2) -0.0659(7) 0.119(8) Uiso 1 1 d D . . . .
H3 H 1.031705 0.404741 -0.071395 0.178 Uiso 1 1 calc R U . . .
C3 C 0.884(2) 0.334(2) -0.0521(7) 0.077(9) Uiso 1 1 d D . . . .
H3A H 0.905412 0.386307 -0.031093 0.116 Uiso 1 1 calc R U . . .
H3B H 0.828796 0.254970 -0.044163 0.116 Uiso 1 1 calc R U . . .
H3C H 0.849282 0.357765 -0.071258 0.116 Uiso 1 1 calc R U . . .
O4 O 0.711(3) 0.065(3) 0.0148(8) 0.150(10) Uiso 1 1 d D . . . .
H4 H 0.768757 0.099536 0.001070 0.225 Uiso 1 1 calc R U . . .
C4 C 0.642(3) 0.114(3) 0.0111(10) 0.144(17) Uiso 1 1 d D . . . .
H4A H 0.571656 0.071131 0.025891 0.216 Uiso 1 1 calc R U . . .
H4B H 0.620205 0.112074 -0.014803 0.216 Uiso 1 1 calc R U . . .
H4C H 0.684088 0.194686 0.019443 0.216 Uiso 1 1 calc R U . . .
O5 O 0.942(2) 0.736(2) 0.0386(6) 0.139(10) Uiso 1 1 d D . . . .
H5 H 0.913569 0.682082 0.054183 0.208 Uiso 1 1 calc R U . . .
C5 C 0.980(3) 0.841(3) 0.0561(9) 0.126(14) Uiso 1 1 d D . . . .
H5A H 0.941635 0.827261 0.080080 0.189 Uiso 1 1 calc R U . . .
H5B H 0.960235 0.889203 0.041052 0.189 Uiso 1 1 calc R U . . .
H5C H 1.063461 0.879295 0.059587 0.189 Uiso 1 1 calc R U . . .
O7 O 0.5626(14) 0.5261(15) 0.0823(4) 0.061(5) Uiso 1 1 d D . . . .
H7 H 0.594753 0.486820 0.078692 0.091 Uiso 1 1 calc R U . . .
C7 C 0.635(2) 0.623(2) 0.1031(7) 0.075(9) Uiso 1 1 d D . . . .
H7A H 0.589894 0.654979 0.113965 0.113 Uiso 1 1 calc R U . . .
H7B H 0.695327 0.681073 0.087285 0.113 Uiso 1 1 calc R U . . .
H7C H 0.670520 0.601030 0.122676 0.113 Uiso 1 1 calc R U . . .
O8 O 0.776(3) 0.524(3) 0.0580(9) 0.226(16) Uiso 1 1 d D . . . .
H8 H 0.713177 0.499048 0.046605 0.339 Uiso 1 1 calc R U . . .
C8 C 0.819(4) 0.449(4) 0.0525(10) 0.144(15) Uiso 1 1 d D . . . .
H8A H 0.894553 0.490701 0.040761 0.216 Uiso 1 1 calc R U . . .
H8B H 0.765478 0.384874 0.036680 0.216 Uiso 1 1 calc R U . . .
H8C H 0.825680 0.418300 0.076224 0.216 Uiso 1 1 calc R U . . .
O6 O 0.680(5) 0.601(4) 0.0234(12) 0.130(19) Uiso 0.5 1 d D . P A -1
H6 H 0.652468 0.588589 0.044683 0.194 Uiso 0.5 1 calc R U P A -1
C6 C 0.663(6) 0.685(5) 0.006(2) 0.11(3) Uiso 0.5 1 d D . P A -1
H6A H 0.678901 0.689760 -0.021740 0.161 Uiso 0.5 1 d . U P B -1
H6B H 0.738120 0.767281 0.012750 0.161 Uiso 0.5 1 d . U P C -1
H6C H 0.603230 0.691251 0.010910 0.161 Uiso 0.5 1 d . U P D -1


_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 2.392(14) . ?
Cu1 O11 1.959(13) . ?
Cu1 N11 2.030(15) . ?
Cu1 N12 1.948(15) . ?
Cu1 N23 1.964(16) . ?
Cu2 O2 2.393(15) . ?
Cu2 O21 1.969(14) . ?
Cu2 N13 1.951(16) . ?
Cu2 N21 1.991(17) . ?
Cu2 N22 1.935(15) . ?
O1 H1 0.86(2) . ?
O1 C1 1.409(17) . ?
O2 H2 0.86(2) . ?
O2 C2 1.402(17) . ?
O11 C14 1.23(2) . ?
O12 C14 1.22(2) . ?
O13 C13 1.24(2) . ?
O21 C24 1.29(2) . ?
O22 C24 1.26(2) . ?
O23 C23 1.26(2) . ?
N11 H11A 0.9100 . ?
N11 H11B 0.9100 . ?
N11 C11 1.48(2) . ?
N12 C13 1.36(2) . ?
N12 C15 1.46(2) . ?
N13 C18 1.43(2) . ?
N13 C19 1.30(2) . ?
N14 H14 0.8800 . ?
N14 C17 1.41(2) . ?
N14 C19 1.37(2) . ?
N21 H21A 0.9100 . ?
N21 H21B 0.9100 . ?
N21 C21 1.51(2) . ?
N22 C23 1.27(2) . ?
N22 C25 1.47(2) . ?
N23 C28 1.36(2) . ?
N23 C29 1.35(2) . ?
N24 H24 0.8800 . ?
N24 C27 1.34(2) . ?
N24 C29 1.30(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C11 H11C 0.9900 . ?
C11 H11D 0.9900 . ?
C11 C12 1.55(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.52(3) . ?
C14 C15 1.54(3) . ?
C15 H15 1.0000 . ?
C15 C16 1.53(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.50(3) . ?
C17 C18 1.36(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C21 H21C 0.9900 . ?
C21 H21D 0.9900 . ?
C21 C22 1.49(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.48(3) . ?
C24 C25 1.49(3) . ?
C25 H25 1.0000 . ?
C25 C26 1.55(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.53(3) . ?
C27 C28 1.35(3) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
O3 H3 0.8400 . ?
O3 C3 1.388(18) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
O4 H4 0.8400 . ?
O4 C4 1.384(19) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
O5 H5 0.8400 . ?
O5 C5 1.386(19) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
O7 H7 0.8400 . ?
O7 C7 1.389(17) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
O8 H8 0.8400 . ?
O8 C8 1.39(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O6 H6 0.8400 . ?
O6 C6 1.40(2) . ?
C6 H6A 1.04(8) . ?
C6 H6B 1.08(7) . ?
C6 H6C 0.86(7) . ?

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
O11 Cu1 O1 89.8(5) . . ?
O11 Cu1 N11 173.9(6) . . ?
O11 Cu1 N23 91.9(6) . . ?
N11 Cu1 O1 91.3(6) . . ?
N12 Cu1 O1 103.6(6) . . ?
N12 Cu1 O11 82.7(6) . . ?
N12 Cu1 N11 91.3(6) . . ?
N12 Cu1 N23 162.5(7) . . ?
N23 Cu1 O1 93.0(6) . . ?
N23 Cu1 N11 94.0(6) . . ?
O21 Cu2 O2 85.7(5) . . ?
O21 Cu2 N21 168.9(7) . . ?
N13 Cu2 O2 92.2(6) . . ?
N13 Cu2 O21 91.4(6) . . ?
N13 Cu2 N21 93.9(7) . . ?
N21 Cu2 O2 84.4(6) . . ?
N22 Cu2 O2 108.7(7) . . ?
N22 Cu2 O21 84.5(6) . . ?
N22 Cu2 N13 158.2(8) . . ?
N22 Cu2 N21 94.0(6) . . ?
Cu1 O1 H1 126(4) . . ?
C1 O1 Cu1 118.9(14) . . ?
C1 O1 H1 107(4) . . ?
Cu2 O2 H2 127(4) . . ?
C2 O2 Cu2 124.4(16) . . ?
C2 O2 H2 107(4) . . ?
C14 O11 Cu1 118.3(13) . . ?
C24 O21 Cu2 114.1(13) . . ?
Cu1 N11 H11A 110.4 . . ?
Cu1 N11 H11B 110.4 . . ?
H11A N11 H11B 108.6 . . ?
C11 N11 Cu1 106.5(12) . . ?
C11 N11 H11A 110.4 . . ?
C11 N11 H11B 110.4 . . ?
C13 N12 Cu1 132.9(14) . . ?
C13 N12 C15 117.0(16) . . ?
C15 N12 Cu1 109.7(13) . . ?
C18 N13 Cu2 128.8(12) . . ?
C19 N13 Cu2 125.7(15) . . ?
C19 N13 C18 105.5(16) . . ?
C17 N14 H14 126.2 . . ?
C19 N14 H14 126.2 . . ?
C19 N14 C17 107.5(16) . . ?
Cu2 N21 H21A 109.4 . . ?
Cu2 N21 H21B 109.4 . . ?
H21A N21 H21B 108.0 . . ?
C21 N21 Cu2 111.2(13) . . ?
C21 N21 H21A 109.4 . . ?
C21 N21 H21B 109.4 . . ?
C23 N22 Cu2 132.9(15) . . ?
C23 N22 C25 116.6(17) . . ?
C25 N22 Cu2 109.9(11) . . ?
C28 N23 Cu1 131.9(15) . . ?
C29 N23 Cu1 125.3(14) . . ?
C29 N23 C28 102.7(17) . . ?
C27 N24 H24 125.9 . . ?
C29 N24 H24 125.9 . . ?
C29 N24 C27 108.2(18) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N11 C11 H11C 109.4 . . ?
N11 C11 H11D 109.4 . . ?
N11 C11 C12 111.2(18) . . ?
H11C C11 H11D 108.0 . . ?
C12 C11 H11C 109.4 . . ?
C12 C11 H11D 109.4 . . ?
C11 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 C11 114.4(18) . . ?
C13 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
O13 C13 N12 121.5(19) . . ?
O13 C13 C12 119.9(19) . . ?
N12 C13 C12 118.5(18) . . ?
O11 C14 C15 113.8(18) . . ?
O12 C14 O11 130(2) . . ?
O12 C14 C15 116.0(17) . . ?
N12 C15 C14 110.0(16) . . ?
N12 C15 H15 109.1 . . ?
N12 C15 C16 109.9(17) . . ?
C14 C15 H15 109.1 . . ?
C16 C15 C14 109.7(17) . . ?
C16 C15 H15 109.1 . . ?
C15 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 C15 111.8(17) . . ?
C17 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
N14 C17 C16 119.3(17) . . ?
C18 C17 N14 105.1(17) . . ?
C18 C17 C16 135(2) . . ?
N13 C18 H18 125.1 . . ?
C17 C18 N13 109.8(18) . . ?
C17 C18 H18 125.1 . . ?
N13 C19 N14 112(2) . . ?
N13 C19 H19 123.9 . . ?
N14 C19 H19 123.9 . . ?
N21 C21 H21C 109.1 . . ?
N21 C21 H21D 109.1 . . ?
H21C C21 H21D 107.9 . . ?
C22 C21 N21 112.3(17) . . ?
C22 C21 H21C 109.1 . . ?
C22 C21 H21D 109.1 . . ?
C21 C22 H22A 107.9 . . ?
C21 C22 H22B 107.9 . . ?
H22A C22 H22B 107.2 . . ?
C23 C22 C21 117.8(18) . . ?
C23 C22 H22A 107.9 . . ?
C23 C22 H22B 107.9 . . ?
O23 C23 N22 126(2) . . ?
O23 C23 C22 115.5(17) . . ?
N22 C23 C22 118.2(18) . . ?
O21 C24 C25 116.3(19) . . ?
O22 C24 O21 123.8(19) . . ?
O22 C24 C25 119.4(19) . . ?
N22 C25 C24 110.5(16) . . ?
N22 C25 H25 108.2 . . ?
N22 C25 C26 112.5(18) . . ?
C24 C25 H25 108.2 . . ?
C24 C25 C26 109.2(17) . . ?
C26 C25 H25 108.2 . . ?
C25 C26 H26A 109.4 . . ?
C25 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
C27 C26 C25 111.0(17) . . ?
C27 C26 H26A 109.4 . . ?
C27 C26 H26B 109.4 . . ?
N24 C27 C26 122.4(18) . . ?
N24 C27 C28 105.6(17) . . ?
C28 C27 C26 131.8(19) . . ?
N23 C28 H28 124.5 . . ?
C27 C28 N23 111.0(19) . . ?
C27 C28 H28 124.5 . . ?
N23 C29 H29 123.9 . . ?
N24 C29 N23 112.3(19) . . ?
N24 C29 H29 123.9 . . ?
C3 O3 H3 109.5 . . ?
O3 C3 H3A 109.5 . . ?
O3 C3 H3B 109.5 . . ?
O3 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 O4 H4 109.5 . . ?
O4 C4 H4A 109.5 . . ?
O4 C4 H4B 109.5 . . ?
O4 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C5 O5 H5 109.5 . . ?
O5 C5 H5A 109.5 . . ?
O5 C5 H5B 109.5 . . ?
O5 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 O7 H7 109.5 . . ?
O7 C7 H7A 109.5 . . ?
O7 C7 H7B 109.5 . . ?
O7 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 O8 H8 109.5 . . ?
O8 C8 H8A 109.5 . . ?
O8 C8 H8B 109.5 . . ?
O8 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 O6 H6 109.5 . . ?
O6 C6 H6A 112(7) . . ?
O6 C6 H6B 106(5) . . ?
O6 C6 H6C 121(6) . . ?
H6A C6 H6B 96(5) . . ?
H6A C6 H6C 111(6) . . ?
H6B C6 H6C 107(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O3 0.86(2) 1.93(10) 2.65(3) 141(12) 4_645 yes
O2 H2 O13 0.86(2) 2.03(14) 2.651(19) 128(15) 6_875 yes
N14 H14 O22 0.88 1.82 2.69(2) 171.1 6_765 yes
N24 H24 O12 0.88 1.88 2.76(2) 172.9 6_765 yes
O5 H5 O8 0.84 2.00 2.68(5) 137.4 . yes
O8 H8 O6 0.84 1.83 2.37(6) 119.9 . yes
O6 H6 O7 0.84 1.74 2.55(5) 162.7 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O11 C14 O12 176.1(18) . . . . ?
Cu1 O11 C14 C15 3(2) . . . . ?
Cu1 N11 C11 C12 -78.4(17) . . . . ?
Cu1 N12 C13 O13 178.2(14) . . . . ?
Cu1 N12 C13 C12 1(3) . . . . ?
Cu1 N12 C15 C14 25.2(19) . . . . ?
Cu1 N12 C15 C16 -95.8(16) . . . . ?
Cu1 N23 C28 C27 -172.0(14) . . . . ?
Cu1 N23 C29 N24 174.3(13) . . . . ?
Cu2 O21 C24 O22 179.7(16) . . . . ?
Cu2 O21 C24 C25 7(2) . . . . ?
Cu2 N13 C18 C17 -176.2(14) . . . . ?
Cu2 N13 C19 N14 175.7(13) . . . . ?
Cu2 N21 C21 C22 -63(2) . . . . ?
Cu2 N22 C23 O23 174.4(15) . . . . ?
Cu2 N22 C23 C22 -6(3) . . . . ?
Cu2 N22 C25 C24 23(2) . . . . ?
Cu2 N22 C25 C26 -98.9(16) . . . . ?
O11 C14 C15 N12 -19(2) . . . . ?
O11 C14 C15 C16 102(2) . . . . ?
O12 C14 C15 N12 166.9(17) . . . . ?
O12 C14 C15 C16 -72(2) . . . . ?
O21 C24 C25 N22 -20(2) . . . . ?
O21 C24 C25 C26 104(2) . . . . ?
O22 C24 C25 N22 166.6(18) . . . . ?
O22 C24 C25 C26 -69(2) . . . . ?
N11 C11 C12 C13 66(2) . . . . ?
N12 C15 C16 C17 68(2) . . . . ?
N14 C17 C18 N13 1(2) . . . . ?
N21 C21 C22 C23 66(3) . . . . ?
N22 C25 C26 C27 68(2) . . . . ?
N24 C27 C28 N23 -5(2) . . . . ?
C11 C12 C13 O13 160.4(19) . . . . ?
C11 C12 C13 N12 -22(3) . . . . ?
C13 N12 C15 C14 -160.8(18) . . . . ?
C13 N12 C15 C16 78(2) . . . . ?
C14 C15 C16 C17 -54(2) . . . . ?
C15 N12 C13 O13 6(3) . . . . ?
C15 N12 C13 C12 -171.7(18) . . . . ?
C15 C16 C17 N14 95(2) . . . . ?
C15 C16 C17 C18 -77(3) . . . . ?
C16 C17 C18 N13 173(2) . . . . ?
C17 N14 C19 N13 1(2) . . . . ?
C18 N13 C19 N14 -1(2) . . . . ?
C19 N13 C18 C17 0(2) . . . . ?
C19 N14 C17 C16 -175.2(18) . . . . ?
C19 N14 C17 C18 -1(2) . . . . ?
C21 C22 C23 O23 151.6(18) . . . . ?
C21 C22 C23 N22 -28(3) . . . . ?
C23 N22 C25 C24 -164.5(18) . . . . ?
C23 N22 C25 C26 73(2) . . . . ?
C24 C25 C26 C27 -55(2) . . . . ?
C25 N22 C23 O23 4(3) . . . . ?
C25 N22 C23 C22 -175.9(18) . . . . ?
C25 C26 C27 N24 91(2) . . . . ?
C25 C26 C27 C28 -83(3) . . . . ?
C26 C27 C28 N23 170(2) . . . . ?
C27 N24 C29 N23 -1(2) . . . . ?
C28 N23 C29 N24 -2(2) . . . . ?
C29 N23 C28 C27 4(2) . . . . ?
C29 N24 C27 C26 -172.2(19) . . . . ?
C29 N24 C27 C28 3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.408
_oxdiff_exptl_absorpt_empirical_full_min 0.868
# start Validation Reply Form
_vrf_PLAT029_3                   
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.859 Why?
RESPONSE: The crystals decomposed fast when taken out of the methanol
solution and continued to decompose during data collection. The diffraction 
was not up to high resolution. Only a fast and unique data set was collected.
;
_vrf_PLAT201_3                   
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) ....... 20 Report
RESPONSE: Because of the described decomposition the number of data was 
low not allowing anisotropic refinement of most atoms. Only copper and 
heteroatoms from the complex were refined anisotropically.
;
_vrf_PLAT021_3                   
;
PROBLEM: Ratio Unique / Expected Reflections too High ... 3.711
RESPONSE: The crystals decomposed fast when taken out of the methanol
solution and continued to decompose during data collection. The diffraction 
was not up to high resolution. Only a fast and unique data set was collected.

;
_vrf_PLAT341_3                   
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.03083 Ang.
RESPONSE: The crystals decomposed fast when taken out of the methanol
solution and continued to decompose during data collection. The diffraction 
was not up to high resolution. Only a fast and unique data set was collected.

;
_vrf_PLAT417_3                   
;
PROBLEM: Short Inter D-H..H-D H1 ..H3 . 1.91 Ang.
RESPONSE: The solvent methanol molecules had fixed geometry not allowing for rotation of the methyl group.
;
_vrf_PLAT420_3                   
;
PROBLEM: D-H Bond Without Acceptor O3 --H3 . Please Check
RESPONSE: The solvent methanol molecules had fixed geometry not allowing for rotation of the OH group.
;
_vrf_PLAT910_3                   
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 30 Note
RESPONSE: Some low resolution data had high error/esd values and were omitted.
;
_vrf_PLAT911_3                   
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PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.592 492 Report
RESPONSE: Some data had high error/esd values and were omitted.
;
# end Validation Reply Form
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
