# Supplementary Information (SI) for RSC Sustainability.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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 
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data_220922_ch_gc3n947ms_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2381054'
loop_
_audit_author_name
_audit_author_address
'Chris Hebert Franco'
;Instituto Superior Tecnico, Universidade de Lisboa
Portugal
;
_audit_update_record             
;
2024-08-31 deposited with the CCDC.	2025-05-19 downloaded from the CCDC.
;
_audit_creation_date             2023-08-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
chris.franco@tecnico.ulisboa.pt
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H23 Cu2 N3 O12, 2(H2 O)'
_chemical_formula_sum            'C19 H27 Cu2 N3 O14'
_chemical_formula_weight         648.51
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.9122(6)
_cell_length_b                   10.8868(4)
_cell_length_c                   16.8263(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.444(2)
_cell_angle_gamma                90
_cell_volume                     2527.02(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      30.395
_cell_measurement_theta_min      2.384
_shelx_estimated_absorpt_T_max   0.872
_shelx_estimated_absorpt_T_min   0.817
_exptl_absorpt_coefficient_mu    1.758
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0754 before and 0.0540 after correction.
The Ratio of minimum to maximum transmission is 0.9144.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            49574
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.234
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4087
_reflns_number_total             4615
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         2.788
_refine_diff_density_min         -1.569
_refine_diff_density_rms         0.143
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4615
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0589
_refine_ls_restrained_S_all      1.045
_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)+(0.0949P)²+16.4648P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1678
_refine_ls_wR_factor_ref         0.1744
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O12-H12
 0.85 with sigma of 0.01
 O11-H11
 0.85 with sigma of 0.01
 C15-H11
 1.882622 with sigma of 0.02
 Cu2-H12
 2.673915 with sigma of 0.02
 Cu2-H11
 2.940929 with sigma of 0.02
 C17-H12
 1.898685 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C15) = Uanis(C16) = Uanis(C19) = Uanis(C18) = Uanis(C17) = Uanis(N3)
4.a Free rotating group:
 O13(H13A,H13B), O14(H14A,H14B)
4.b Rotating group:
 O9(H9A,H9B), O10(H10A,H10B)
4.c Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B), C16(H16A,H16B), C18(H18A,H18B)
4.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C12(H12A), C11(H11A), C4(H4), C5(H5), C10(H10)
4.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.24535(4) 0.33496(5) 0.21453(3) 0.01601(19) Uani 1 1 d . . . . .
Cu2 Cu 0.22486(5) 0.76493(6) 0.52377(4) 0.0266(2) Uani 1 1 d D . . . .
O4 O 0.1547(2) 0.4736(3) 0.2227(2) 0.0210(7) Uani 1 1 d . . . . .
O5 O 0.3353(2) 0.1941(3) 0.2091(2) 0.0254(8) Uani 1 1 d . . . . .
O1 O 0.0962(3) 0.7224(4) 0.4658(2) 0.0324(9) Uani 1 1 d . . . . .
O3 O 0.1225(3) 0.4049(4) 0.3413(2) 0.0386(10) Uani 1 1 d . . . . .
N2 N 0.6423(3) -0.0472(4) 0.2806(3) 0.0207(9) Uani 1 1 d . . . . .
N1 N -0.1341(3) 0.7180(4) 0.2825(3) 0.0195(8) Uani 1 1 d . . . . .
O2 O 0.1948(3) 0.6678(4) 0.3785(2) 0.0355(10) Uani 1 1 d . . . . .
O6 O 0.3779(4) 0.2391(4) 0.3369(3) 0.0416(11) Uani 1 1 d . . . . .
O9 O 0.2240(3) 0.3441(4) 0.0711(3) 0.0426(11) Uani 1 1 d . . . . .
H9A H 0.266189 0.298526 0.052891 0.064 Uiso 1 1 d R U . . .
H9B H 0.169750 0.311522 0.052821 0.064 Uiso 1 1 d R U . . .
O12 O 0.3683(3) 0.7756(5) 0.5433(3) 0.0469(12) Uani 1 1 d D . . . .
H12 H 0.4084(16) 0.819(3) 0.520(3) 0.070 Uiso 1 1 d D U . . .
O7 O 0.3280(3) -0.0255(5) 0.3582(3) 0.0490(13) Uani 1 1 d . . . . .
O10 O 0.2150(4) 0.9312(4) 0.4774(3) 0.0476(11) Uani 1 1 d . . . . .
H10A H 0.239321 0.931298 0.433393 0.071 Uiso 1 1 d R U . . .
H10B H 0.250793 0.980697 0.507352 0.071 Uiso 1 1 d R U . . .
N3 N 0.2492(6) 0.6006(7) 0.5801(4) 0.0633(9) Uani 1 1 d . . . . .
C7 C 0.1082(3) 0.4741(4) 0.2837(3) 0.0203(10) Uani 1 1 d . . . . .
O11 O 0.1713(5) 0.8119(4) 0.6387(3) 0.0587(15) Uani 1 1 d D . . . .
H11 H 0.157(7) 0.874(2) 0.666(2) 0.088 Uiso 1 1 d D U . . .
C3 C -0.0557(3) 0.7316(4) 0.3359(3) 0.0191(10) Uani 1 1 d . . . . .
H3 H -0.055541 0.793549 0.373948 0.023 Uiso 1 1 calc R U . . .
C2 C 0.0261(3) 0.6578(4) 0.3375(3) 0.0190(10) Uani 1 1 d . . . . .
C1 C 0.1133(4) 0.6835(5) 0.3975(3) 0.0230(11) Uani 1 1 d . . . . .
C13 C 0.4878(4) -0.0068(5) 0.3258(3) 0.0236(11) Uani 1 1 d . . . . .
C12 C 0.5724(4) -0.0735(5) 0.3265(3) 0.0230(10) Uani 1 1 d . . . . .
H12A H 0.581748 -0.140696 0.360742 0.028 Uiso 1 1 calc R U . . .
O8 O 0.4455(4) -0.1230(6) 0.4333(4) 0.072(2) Uani 1 1 d . . . . .
C6 C 0.0256(3) 0.5652(4) 0.2802(3) 0.0192(10) Uani 1 1 d . . . . .
C11 C 0.6282(4) 0.0495(5) 0.2319(3) 0.0275(11) Uani 1 1 d . . . . .
H11A H 0.675491 0.069161 0.199713 0.033 Uiso 1 1 calc R U . . .
C8 C 0.3880(4) 0.1817(5) 0.2755(3) 0.0237(11) Uani 1 1 d . . . . .
C9 C 0.4740(3) 0.0948(5) 0.2757(3) 0.0223(10) Uani 1 1 d . . . . .
C4 C -0.1343(4) 0.6299(5) 0.2263(3) 0.0251(11) Uani 1 1 d . . . . .
H4 H -0.188811 0.620036 0.188579 0.030 Uiso 1 1 calc R U . . .
O13 O 0.0743(4) 0.2389(7) 0.4624(4) 0.0717(18) Uani 1 1 d G . . . .
H13A H 0.086145 0.292376 0.428129 0.108 Uiso 1 1 d G U . . .
H13B H 0.021348 0.262473 0.477652 0.108 Uiso 1 1 d G U . . .
C5 C -0.0555(4) 0.5538(5) 0.2235(3) 0.0250(11) Uani 1 1 d . . . . .
H5 H -0.056798 0.494822 0.183397 0.030 Uiso 1 1 calc R U . . .
O14 O 0.3791(4) 0.2220(9) 0.5003(4) 0.085(2) Uani 1 1 d G . . . .
H14A H 0.428673 0.176147 0.501506 0.128 Uiso 1 1 d G U . . .
H14B H 0.370627 0.250448 0.452844 0.128 Uiso 1 1 d G U . . .
C10 C 0.5457(4) 0.1217(5) 0.2277(3) 0.0280(12) Uani 1 1 d . . . . .
H10 H 0.538153 0.188236 0.192704 0.034 Uiso 1 1 calc R U . . .
C14 C 0.4131(4) -0.0541(5) 0.3766(4) 0.0333(13) Uani 1 1 d . . . . .
C15 C 0.1805(7) 0.7074(8) 0.6898(5) 0.0633(9) Uani 1 1 d D . . . .
H15A H 0.119056 0.664413 0.686179 0.076 Uiso 1 1 calc R U . . .
H15B H 0.198323 0.733174 0.744904 0.076 Uiso 1 1 calc R U . . .
C17 C 0.4141(7) 0.6596(8) 0.5613(6) 0.0633(9) Uani 1 1 d D . . . .
H17A H 0.449153 0.661373 0.615019 0.076 Uiso 1 1 calc R U . . .
H17B H 0.460193 0.643525 0.523997 0.076 Uiso 1 1 calc R U . . .
C16 C 0.2558(7) 0.6245(8) 0.6655(5) 0.0633(9) Uani 1 1 d . . . . .
H16A H 0.318904 0.659800 0.683445 0.076 Uiso 1 1 calc R U . . .
H16B H 0.252021 0.546698 0.693093 0.076 Uiso 1 1 calc R U . . .
C19 C 0.1785(7) 0.5029(8) 0.5566(5) 0.0633(9) Uani 1 1 d . . . . .
H19A H 0.114358 0.537010 0.549417 0.095 Uiso 1 1 calc R U . . .
H19B H 0.182962 0.441346 0.597824 0.095 Uiso 1 1 calc R U . . .
H19C H 0.192006 0.466376 0.507344 0.095 Uiso 1 1 calc R U . . .
C18 C 0.3380(7) 0.5574(8) 0.5553(5) 0.0633(9) Uani 1 1 d . . . . .
H18A H 0.325843 0.528385 0.500432 0.076 Uiso 1 1 calc R U . . .
H18B H 0.362475 0.488901 0.588922 0.076 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 O4 1.983(3) . ?
Cu1 O5 1.989(4) . ?
Cu1 N2 2.016(4) 2_655 ?
Cu1 N1 2.009(4) 2_545 ?
Cu1 O9 2.395(4) . ?
Cu2 O1 1.979(4) . ?
Cu2 O12 1.984(4) . ?
Cu2 O10 1.969(5) . ?
Cu2 N3 2.032(7) . ?
Cu2 O11 2.221(5) . ?
O4 C7 1.282(6) . ?
O5 C8 1.261(7) . ?
O1 C1 1.276(7) . ?
O3 C7 1.224(6) . ?
N2 C12 1.348(6) . ?
N2 C11 1.333(7) . ?
N1 C3 1.328(7) . ?
N1 C4 1.347(7) . ?
O2 C1 1.229(6) . ?
O6 C8 1.232(7) . ?
O9 H9A 0.8547 . ?
O9 H9B 0.8546 . ?
O12 H12 0.864(10) . ?
O12 C17 1.429(10) . ?
O7 C14 1.224(7) . ?
O10 H10A 0.8523 . ?
O10 H10B 0.8526 . ?
N3 C16 1.452(11) . ?
N3 C19 1.468(11) . ?
N3 C18 1.433(11) . ?
C7 C6 1.513(6) . ?
O11 H11 0.852(9) . ?
O11 C15 1.422(9) . ?
C3 H3 0.9300 . ?
C3 C2 1.391(7) . ?
C2 C1 1.501(7) . ?
C2 C6 1.395(7) . ?
C13 C12 1.382(7) . ?
C13 C9 1.389(7) . ?
C13 C14 1.518(7) . ?
C12 H12A 0.9300 . ?
O8 C14 1.251(8) . ?
C6 C5 1.385(7) . ?
C11 H11A 0.9300 . ?
C11 C10 1.386(7) . ?
C8 C9 1.525(7) . ?
C9 C10 1.395(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(7) . ?
O13 H13A 0.8506 . ?
O13 H13B 0.8503 . ?
C5 H5 0.9300 . ?
O14 H14A 0.8498 . ?
O14 H14B 0.8498 . ?
C10 H10 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.479(12) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.530(12) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?

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
O4 Cu1 O5 178.47(15) . . ?
O4 Cu1 N2 90.55(15) . 2_655 ?
O4 Cu1 N1 88.98(15) . 2_545 ?
O4 Cu1 O9 92.38(16) . . ?
O5 Cu1 N2 90.16(16) . 2_655 ?
O5 Cu1 N1 90.22(16) . 2_545 ?
O5 Cu1 O9 88.97(16) . . ?
N2 Cu1 O9 90.50(16) 2_655 . ?
N1 Cu1 N2 176.29(17) 2_545 2_655 ?
N1 Cu1 O9 93.20(16) 2_545 . ?
O1 Cu2 O12 157.2(2) . . ?
O1 Cu2 N3 96.3(3) . . ?
O1 Cu2 O11 95.7(2) . . ?
O12 Cu2 N3 82.6(3) . . ?
O12 Cu2 O11 106.6(2) . . ?
O10 Cu2 O1 90.4(2) . . ?
O10 Cu2 O12 91.6(2) . . ?
O10 Cu2 N3 173.2(3) . . ?
O10 Cu2 O11 96.9(2) . . ?
N3 Cu2 O11 81.4(2) . . ?
C7 O4 Cu1 116.8(3) . . ?
C8 O5 Cu1 109.8(3) . . ?
C1 O1 Cu2 105.0(3) . . ?
C12 N2 Cu1 117.1(3) . 2_645 ?
C11 N2 Cu1 125.4(3) . 2_645 ?
C11 N2 C12 117.4(4) . . ?
C3 N1 Cu1 118.7(3) . 2 ?
C3 N1 C4 118.7(4) . . ?
C4 N1 Cu1 122.5(3) . 2 ?
Cu1 O9 H9A 109.7 . . ?
Cu1 O9 H9B 109.5 . . ?
H9A O9 H9B 104.2 . . ?
Cu2 O12 H12 131(2) . . ?
C17 O12 Cu2 113.2(5) . . ?
C17 O12 H12 106.5(19) . . ?
Cu2 O10 H10A 109.3 . . ?
Cu2 O10 H10B 109.9 . . ?
H10A O10 H10B 104.3 . . ?
C16 N3 Cu2 106.8(5) . . ?
C16 N3 C19 110.5(7) . . ?
C19 N3 Cu2 116.5(5) . . ?
C18 N3 Cu2 104.6(5) . . ?
C18 N3 C16 113.6(7) . . ?
C18 N3 C19 104.9(7) . . ?
O4 C7 C6 115.5(4) . . ?
O3 C7 O4 125.7(4) . . ?
O3 C7 C6 118.7(4) . . ?
Cu2 O11 H11 141(2) . . ?
C15 O11 Cu2 109.1(5) . . ?
C15 O11 H11 108.9(18) . . ?
N1 C3 H3 118.4 . . ?
N1 C3 C2 123.2(5) . . ?
C2 C3 H3 118.4 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 C6 118.2(4) . . ?
C6 C2 C1 122.1(4) . . ?
O1 C1 C2 116.0(4) . . ?
O2 C1 O1 124.5(5) . . ?
O2 C1 C2 119.5(5) . . ?
C12 C13 C9 118.3(5) . . ?
C12 C13 C14 117.5(5) . . ?
C9 C13 C14 124.1(4) . . ?
N2 C12 C13 124.1(5) . . ?
N2 C12 H12A 117.9 . . ?
C13 C12 H12A 117.9 . . ?
C2 C6 C7 120.7(4) . . ?
C5 C6 C7 121.0(4) . . ?
C5 C6 C2 118.1(4) . . ?
N2 C11 H11A 118.8 . . ?
N2 C11 C10 122.4(5) . . ?
C10 C11 H11A 118.8 . . ?
O5 C8 C9 115.8(5) . . ?
O6 C8 O5 124.9(5) . . ?
O6 C8 C9 119.1(5) . . ?
C13 C9 C8 122.8(4) . . ?
C13 C9 C10 117.8(5) . . ?
C10 C9 C8 119.2(5) . . ?
N1 C4 H4 119.2 . . ?
N1 C4 C5 121.5(5) . . ?
C5 C4 H4 119.2 . . ?
H13A O13 H13B 104.5 . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.2(5) . . ?
C4 C5 H5 119.9 . . ?
H14A O14 H14B 104.5 . . ?
C11 C10 C9 120.0(5) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
O7 C14 C13 118.8(5) . . ?
O7 C14 O8 125.9(5) . . ?
O8 C14 C13 115.3(5) . . ?
O11 C15 H15A 109.8 . . ?
O11 C15 H15B 109.8 . . ?
O11 C15 C16 109.5(7) . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 H15A 109.8 . . ?
C16 C15 H15B 109.8 . . ?
O12 C17 H17A 109.6 . . ?
O12 C17 H17B 109.6 . . ?
O12 C17 C18 110.1(7) . . ?
H17A C17 H17B 108.2 . . ?
C18 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
N3 C16 C15 115.2(8) . . ?
N3 C16 H16A 108.5 . . ?
N3 C16 H16B 108.5 . . ?
C15 C16 H16A 108.5 . . ?
C15 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C18 C17 110.9(7) . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O4 C7 O3 8.6(7) . . . . ?
Cu1 O4 C7 C6 -168.1(3) . . . . ?
Cu1 O5 C8 O6 7.4(7) . . . . ?
Cu1 O5 C8 C9 -168.1(3) . . . . ?
Cu1 N2 C12 C13 -175.4(4) 2_645 . . . ?
Cu1 N2 C11 C10 175.3(4) 2_645 . . . ?
Cu1 N1 C3 C2 -178.2(4) 2 . . . ?
Cu1 N1 C4 C5 177.3(4) 2 . . . ?
Cu2 O1 C1 O2 5.7(7) . . . . ?
Cu2 O1 C1 C2 -173.4(3) . . . . ?
Cu2 O12 C17 C18 3.4(8) . . . . ?
Cu2 N3 C16 C15 44.9(9) . . . . ?
Cu2 N3 C18 C17 46.1(8) . . . . ?
Cu2 O11 C15 C16 23.0(9) . . . . ?
O4 C7 C6 C2 -119.3(5) . . . . ?
O4 C7 C6 C5 65.3(6) . . . . ?
O5 C8 C9 C13 -122.5(6) . . . . ?
O5 C8 C9 C10 61.8(7) . . . . ?
O3 C7 C6 C2 63.8(7) . . . . ?
O3 C7 C6 C5 -111.7(6) . . . . ?
N2 C11 C10 C9 0.4(9) . . . . ?
N1 C3 C2 C1 177.1(4) . . . . ?
N1 C3 C2 C6 0.2(7) . . . . ?
N1 C4 C5 C6 1.4(8) . . . . ?
O6 C8 C9 C13 61.8(7) . . . . ?
O6 C8 C9 C10 -114.0(6) . . . . ?
O12 C17 C18 N3 -33.9(10) . . . . ?
C7 C6 C5 C4 173.3(5) . . . . ?
O11 C15 C16 N3 -46.5(10) . . . . ?
C3 N1 C4 C5 0.3(8) . . . . ?
C3 C2 C1 O1 35.3(7) . . . . ?
C3 C2 C1 O2 -143.9(5) . . . . ?
C3 C2 C6 C7 -174.1(4) . . . . ?
C3 C2 C6 C5 1.5(7) . . . . ?
C2 C6 C5 C4 -2.3(8) . . . . ?
C1 C2 C6 C7 9.1(7) . . . . ?
C1 C2 C6 C5 -175.3(5) . . . . ?
C13 C9 C10 C11 -1.2(8) . . . . ?
C12 N2 C11 C10 0.1(8) . . . . ?
C12 C13 C9 C8 -174.4(5) . . . . ?
C12 C13 C9 C10 1.4(8) . . . . ?
C12 C13 C14 O7 -155.6(6) . . . . ?
C12 C13 C14 O8 22.5(9) . . . . ?
C6 C2 C1 O1 -148.0(5) . . . . ?
C6 C2 C1 O2 32.8(7) . . . . ?
C11 N2 C12 C13 0.2(8) . . . . ?
C8 C9 C10 C11 174.8(5) . . . . ?
C9 C13 C12 N2 -1.0(8) . . . . ?
C9 C13 C14 O7 20.7(9) . . . . ?
C9 C13 C14 O8 -161.2(6) . . . . ?
C4 N1 C3 C2 -1.1(7) . . . . ?
C14 C13 C12 N2 175.5(5) . . . . ?
C14 C13 C9 C8 9.4(8) . . . . ?
C14 C13 C9 C10 -174.8(5) . . . . ?
C16 N3 C18 C17 -70.0(9) . . . . ?
C19 N3 C16 C15 -82.8(9) . . . . ?
C19 N3 C18 C17 169.2(7) . . . . ?
C18 N3 C16 C15 159.7(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT971_220922_ch_gc3n947ms_0m_a 
;
PROBLEM: Check Calcd Resid. Dens.  0.14Ang From N3              2.95 eA-3  
RESPONSE: The crystals showed weak diffuse scattering due to the slight disorder
effect from aminoalcohol ligand. Constrains were applied in the model (EADP) and
would be responsible for the source of the high electron density in N3.
The slight disorder effect was not considered to model.
;
# 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_mo_xs_42_2022_0ma
_database_code_depnum_ccdc_archive 'CCDC 2381055'
loop_
_audit_author_name
_audit_author_address
'Chris Hebert Franco'
;Instituto Superior Tecnico, Universidade de Lisboa
Portugal
;
_audit_update_record             
;
2024-08-31 deposited with the CCDC.	2025-05-19 downloaded from the CCDC.
;
_audit_creation_date             2023-08-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
chris.franco@tecnico.ulisboa.pt
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H30 Cu2 N3 O13, 4(H2 O)'
_chemical_formula_sum            'C23 H38 Cu2 N3 O17'
_chemical_formula_weight         755.64
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.6112(11)
_cell_length_b                   20.3103(11)
_cell_length_c                   17.6199(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.672(3)
_cell_angle_gamma                90
_cell_volume                     6230.4(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9665
_cell_measurement_temperature    150
_cell_measurement_theta_max      20.977
_cell_measurement_theta_min      2.322
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.446
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1584 before and 0.1016 after correction.
 The Ratio of minimum to maximum transmission is 0.75.

Final HKLF 4 output contains 172915 reflections, Rint = 0.0879
 (51324 with I > 3sig(I), Rint = 0.0634)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark blue'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3128
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5795
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.512
_diffrn_reflns_theta_min         2.038
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture, dual, Photon II'
_diffrn_measurement_method       scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5052
_reflns_number_total             5795
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    ?
_refine_diff_density_max         3.734
_refine_diff_density_min         -4.093
_refine_diff_density_rms         0.150
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         5795
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0632
_refine_ls_restrained_S_all      1.043
_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)+(0.1272P)²+36.9068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1884
_refine_ls_wR_factor_ref         0.1943
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.857(2)
 0.143(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups, All O(H,H,H) groups
3. Restrained distances
 O9-H9
 0.87 with sigma of 0.01
 H10-O10
 0.95 with sigma of 0.02
 C19-H9
 1.91561 with sigma of 0.02
 Cu2-H9
 3.033258 with sigma of 0.02
 Cu3-H14A \\sim Cu3-H14B
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(O11A) = Uanis(O11B)
5. Others
 Fixed Sof: H14A(0.5) H14B(0.5) O11A(0.5) H15C(0.5) H15D(0.5) O11B(0.5)
6.a Free rotating group:
 O14(H14A,H14B), O13(H13A,H13B), O16(H16A,H16B), O18(H18C,H18D), O17(H10,H17D,
 H17E)
6.b Rotating group:
 O12(H12A,H12B), O15(H15C,H15D)
6.c Ternary CH refined with riding coordinates:
 C19(H19), C16(H16), C22(H22)
6.d Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C15(H15A,H15B), C21(H21A,H21B)
6.e Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C12(H12)
6.f Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C23(H23A,H23B,H23C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.25114(4) 0.250000 0.0180(2) Uani 1 2 d S T P . .
Cu2 Cu 0.71675(4) 0.50428(3) 0.52485(4) 0.0314(2) Uani 1 1 d D . . . .
Cu3 Cu 0.000000 0.18501(4) 0.250000 0.0206(2) Uani 1 2 d DS T P . .
O3 O 0.5121(2) 0.25705(18) 0.3631(2) 0.0266(8) Uani 1 1 d . . . . .
O2 O 0.6357(2) 0.44171(19) 0.5418(2) 0.0324(9) Uani 1 1 d . . . . .
O10 O 0.7926(3) 0.4145(2) 0.4560(3) 0.0429(10) Uani 1 1 d D . . . .
N1 N 0.4967(2) 0.3131(2) 0.6346(2) 0.0238(9) Uani 1 1 d . . . . .
O4 O 0.4823(4) 0.3632(2) 0.3530(3) 0.0603(15) Uani 1 1 d . . . . .
O6 O 0.1075(3) 0.2945(3) 0.2428(4) 0.0714(18) Uani 1 1 d . . . . .
O5 O 0.1129(2) 0.1875(2) 0.2619(2) 0.0301(9) Uani 1 1 d . . . . .
O14 O 0.000000 0.0701(3) 0.250000 0.0476(15) Uani 1 2 d GS T P . .
H14A H 0.015352 0.057447 0.296998 0.071 Uiso 0.5 1 d DG U P . .
H14B H 0.036322 0.057345 0.224886 0.071 Uiso 0.5 1 d DG U P . .
O8 O 0.2920(3) 0.1056(3) 0.3733(3) 0.0645(16) Uani 1 1 d . . . . .
O13 O 0.4923(3) 0.4955(2) 0.3856(3) 0.0510(12) Uani 1 1 d G . . . .
H13A H 0.452266 0.510996 0.403041 0.077 Uiso 1 1 d G U . . .
H13B H 0.480467 0.454767 0.373897 0.077 Uiso 1 1 d G U . . .
O16 O 0.4298(4) 0.0489(3) 0.3430(4) 0.0727(17) Uani 1 1 d G . . . .
H16A H 0.437102 0.062718 0.297966 0.109 Uiso 1 1 d G U . . .
H16B H 0.385808 0.065792 0.349523 0.109 Uiso 1 1 d G U . . .
O18 O 0.2645(9) 0.3210(4) 0.4239(6) 0.138(4) Uani 1 1 d G . . . .
H18C H 0.294596 0.298880 0.398485 0.208 Uiso 1 1 d G U . . .
H18D H 0.226091 0.294625 0.426791 0.208 Uiso 1 1 d G U . . .
O1 O 0.6459(3) 0.3720(2) 0.4466(2) 0.0458(11) Uani 1 1 d . . . . .
N2 N 0.3859(2) 0.24850(19) 0.2465(3) 0.0209(9) Uani 1 1 d . . . . .
O7 O 0.2205(3) 0.1857(3) 0.4107(3) 0.0510(12) Uani 1 1 d . . . . .
C7 C 0.4984(3) 0.3124(3) 0.3905(3) 0.0273(11) Uani 1 1 d . . . . .
C6 C 0.5010(3) 0.3136(2) 0.4765(3) 0.0241(10) Uani 1 1 d . . . . .
C2 C 0.5520(3) 0.3516(2) 0.5263(3) 0.0226(10) Uani 1 1 d . . . . .
C1 C 0.6160(3) 0.3915(3) 0.5013(3) 0.0261(11) Uani 1 1 d . . . . .
O9 O 0.6826(3) 0.5598(2) 0.6283(3) 0.0557(13) Uani 1 1 d D . . . .
H9 H 0.6411(19) 0.577(3) 0.6423(14) 0.084 Uiso 1 1 d D U . . .
C19 C 0.7303(5) 0.5373(4) 0.6972(4) 0.0522(18) Uani 1 1 d D . . . .
H19 H 0.774418 0.568283 0.710478 0.063 Uiso 1 1 calc R U . . .
C18 C 0.7607(4) 0.4698(3) 0.6823(4) 0.0438(15) Uani 1 1 d . . . . .
H18A H 0.800116 0.457235 0.726122 0.053 Uiso 1 1 calc R U . . .
H18B H 0.718219 0.437551 0.679584 0.053 Uiso 1 1 calc R U . . .
N3 N 0.7955(3) 0.4655(2) 0.6095(3) 0.0385(12) Uani 1 1 d . . . . .
C15 C 0.8116(4) 0.3958(3) 0.5946(4) 0.0435(15) Uani 1 1 d . . . . .
H15A H 0.763719 0.370143 0.594240 0.052 Uiso 1 1 calc R U . . .
H15B H 0.849607 0.379047 0.637436 0.052 Uiso 1 1 calc R U . . .
C16 C 0.8418(4) 0.3837(3) 0.5201(4) 0.0451(15) Uani 1 1 d . . . . .
H16 H 0.894110 0.403770 0.524143 0.054 Uiso 1 1 calc R U . . .
C17 C 0.8489(5) 0.3100(4) 0.5049(5) 0.068(2) Uani 1 1 d . . . . .
H17A H 0.797505 0.290496 0.494186 0.102 Uiso 1 1 calc R U . . .
H17B H 0.877981 0.288861 0.550164 0.102 Uiso 1 1 calc R U . . .
H17C H 0.875675 0.303549 0.460612 0.102 Uiso 1 1 calc R U . . .
C21 C 0.8674(4) 0.5070(4) 0.6159(5) 0.0515(17) Uani 1 1 d . . . . .
H21A H 0.867415 0.539198 0.658138 0.062 Uiso 1 1 calc R U . . .
H21B H 0.912991 0.478359 0.628737 0.062 Uiso 1 1 calc R U . . .
C22 C 0.8725(5) 0.5432(5) 0.5425(6) 0.079(3) Uani 1 1 d . . . . .
H22 H 0.889303 0.509611 0.506916 0.095 Uiso 1 1 calc R U . . .
C23 C 0.9339(5) 0.5941(5) 0.5523(6) 0.083(3) Uani 1 1 d . . . . .
H23A H 0.924540 0.625146 0.592496 0.125 Uiso 1 1 calc R U . . .
H23B H 0.933690 0.617848 0.503893 0.125 Uiso 1 1 calc R U . . .
H23C H 0.983930 0.572888 0.567136 0.125 Uiso 1 1 calc R U . . .
O11A O 0.8014(5) 0.5629(5) 0.5090(6) 0.0511(18) Uani 0.5 1 d . . P . .
C20 C 0.6847(6) 0.5349(5) 0.7622(5) 0.071(2) Uani 1 1 d . . . . .
H20A H 0.655438 0.575890 0.763325 0.107 Uiso 1 1 calc R U . . .
H20B H 0.719490 0.529837 0.810737 0.107 Uiso 1 1 calc R U . . .
H20C H 0.649127 0.497537 0.755084 0.107 Uiso 1 1 calc R U . . .
O12 O 0.6462(3) 0.5506(3) 0.4444(3) 0.0618(14) Uani 1 1 d . . . . .
H12A H 0.670100 0.561669 0.405287 0.093 Uiso 1 1 d R U . . .
H12B H 0.609225 0.523745 0.423030 0.093 Uiso 1 1 d R U . . .
C3 C 0.5478(3) 0.3496(3) 0.6040(3) 0.0224(10) Uani 1 1 d . . . . .
H3 H 0.583113 0.375532 0.637524 0.027 Uiso 1 1 calc R U . . .
C4 C 0.4475(3) 0.2768(3) 0.5868(3) 0.0306(12) Uani 1 1 d . . . . .
H4 H 0.411024 0.250455 0.607515 0.037 Uiso 1 1 calc R U . . .
C5 C 0.4476(3) 0.2760(3) 0.5083(3) 0.0306(12) Uani 1 1 d . . . . .
H5 H 0.411294 0.249862 0.476163 0.037 Uiso 1 1 calc R U . . .
C8 C 0.3578(3) 0.2098(3) 0.2968(3) 0.0247(10) Uani 1 1 d . . . . .
H8 H 0.393055 0.184364 0.331036 0.030 Uiso 1 1 calc R U . . .
C9 C 0.2807(3) 0.2043(3) 0.3023(3) 0.0238(10) Uani 1 1 d . . . . .
C10 C 0.2284(3) 0.2430(3) 0.2529(3) 0.0259(11) Uani 1 1 d . . . . .
C13 C 0.1426(3) 0.2429(3) 0.2527(3) 0.0303(12) Uani 1 1 d . . . . .
C11 C 0.2587(3) 0.2826(3) 0.2001(3) 0.0327(12) Uani 1 1 d . . . . .
H11 H 0.225360 0.308687 0.164737 0.039 Uiso 1 1 calc R U . . .
C12 C 0.3368(3) 0.2841(3) 0.1988(3) 0.0286(11) Uani 1 1 d . . . . .
H12 H 0.356168 0.311547 0.162424 0.034 Uiso 1 1 calc R U . . .
C14 C 0.2608(3) 0.1621(3) 0.3668(3) 0.0321(12) Uani 1 1 d . . . . .
O15 O 0.500000 0.1325(3) 0.250000 0.060(2) Uani 1 2 d S T P . .
H15C H 0.493143 0.106043 0.287734 0.090 Uiso 0.5 1 d R U P . .
H15D H 0.506847 0.106043 0.212266 0.090 Uiso 0.5 1 d R U P . .
O11B O 0.7788(5) 0.5004(5) 0.4672(6) 0.0511(18) Uani 0.5 1 d . . P . .
O17 O 0.8836(4) 0.4187(3) 0.3304(4) 0.0782(17) Uani 1 1 d G . . . .
H10 H 0.740466 0.399106 0.447164 0.117 Uiso 1 1 d DG U . . .
H17D H 0.871869 0.405750 0.374218 0.117 Uiso 1 1 d G U . . .
H17E H 0.899081 0.383108 0.309800 0.117 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 O3 1.975(4) . ?
Cu1 O3 1.975(4) 2_655 ?
Cu1 N2 2.003(4) 2_655 ?
Cu1 N2 2.003(4) . ?
Cu1 O15 2.410(7) . ?
Cu2 O2 1.968(4) . ?
Cu2 O9 2.299(5) . ?
Cu2 N3 2.036(5) . ?
Cu2 O11A 1.961(8) . ?
Cu2 O12 1.978(5) . ?
Cu2 O11B 1.602(10) . ?
Cu3 N1 2.026(4) 7_556 ?
Cu3 N1 2.026(4) 8_455 ?
Cu3 O5 1.968(4) 2 ?
Cu3 O5 1.968(4) . ?
Cu3 O14 2.334(6) . ?
O3 C7 1.262(7) . ?
O2 C1 1.263(7) . ?
O10 C16 1.458(8) . ?
O10 O11B 1.776(11) . ?
O10 H10 0.9591 . ?
N1 C3 1.341(6) . ?
N1 C4 1.336(7) . ?
O4 C7 1.235(7) . ?
O6 C13 1.215(7) . ?
O5 C13 1.261(7) . ?
O14 H14A 0.8701 . ?
O14 H14A 0.87(6) 2 ?
O14 H14B 0.87(6) 2 ?
O14 H14B 0.8702 . ?
O8 C14 1.269(8) . ?
O13 H13A 0.8699 . ?
O13 H13B 0.8698 . ?
O16 H16A 0.8695 . ?
O16 H16B 0.8702 . ?
O18 H18C 0.8698 . ?
O18 H18D 0.8701 . ?
O1 C1 1.232(7) . ?
N2 C8 1.335(7) . ?
N2 C12 1.326(7) . ?
O7 C14 1.225(7) . ?
C7 C6 1.508(7) . ?
C6 C2 1.392(7) . ?
C6 C5 1.393(7) . ?
C2 C1 1.506(7) . ?
C2 C3 1.383(7) . ?
O9 H9 0.879(10) . ?
O9 C19 1.443(9) . ?
C19 H19 1.0000 . ?
C19 C18 1.509(10) . ?
C19 C20 1.496(12) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 N3 1.505(8) . ?
N3 C15 1.475(9) . ?
N3 C21 1.511(8) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.509(10) . ?
C16 H16 1.0000 . ?
C16 C17 1.527(11) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.503(11) . ?
C22 H22 1.0000 . ?
C22 C23 1.488(11) . ?
C22 O11A 1.362(12) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O11A O11B 1.493(15) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O12 H12A 0.8880 . ?
O12 H12B 0.8886 . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.383(7) . ?
C5 H5 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.379(7) . ?
C9 C10 1.408(7) . ?
C9 C14 1.507(7) . ?
C10 C13 1.510(7) . ?
C10 C11 1.396(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.380(7) . ?
C12 H12 0.9500 . ?
O15 H15C 0.8768 . ?
O15 H15D 0.8768 . ?
O17 H17D 0.8697 . ?
O17 H17E 0.8703 . ?

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
O3 Cu1 O3 173.0(2) . 2_655 ?
O3 Cu1 N2 89.29(16) . . ?
O3 Cu1 N2 90.90(16) 2_655 . ?
O3 Cu1 N2 90.90(16) . 2_655 ?
O3 Cu1 N2 89.29(16) 2_655 2_655 ?
O3 Cu1 O15 93.48(11) 2_655 . ?
O3 Cu1 O15 93.48(11) . . ?
N2 Cu1 N2 176.9(2) . 2_655 ?
N2 Cu1 O15 88.46(11) 2_655 . ?
N2 Cu1 O15 88.46(11) . . ?
O2 Cu2 O9 85.07(18) . . ?
O2 Cu2 N3 93.93(18) . . ?
O2 Cu2 O12 91.40(19) . . ?
N3 Cu2 O9 80.8(2) . . ?
O11A Cu2 O2 177.0(3) . . ?
O11A Cu2 O9 96.3(4) . . ?
O11A Cu2 N3 83.7(3) . . ?
O11A Cu2 O12 91.0(3) . . ?
O12 Cu2 O9 97.1(2) . . ?
O12 Cu2 N3 174.1(2) . . ?
O11B Cu2 O2 130.1(4) . . ?
O11B Cu2 O9 144.3(4) . . ?
O11B Cu2 N3 89.5(4) . . ?
O11B Cu2 O11A 48.3(5) . . ?
O11B Cu2 O12 89.1(4) . . ?
N1 Cu3 N1 177.8(2) 8_455 7_556 ?
N1 Cu3 O14 91.10(12) 7_556 . ?
N1 Cu3 O14 91.10(12) 8_455 . ?
O5 Cu3 N1 88.96(16) 2 7_556 ?
O5 Cu3 N1 88.96(16) . 8_455 ?
O5 Cu3 N1 90.99(16) . 7_556 ?
O5 Cu3 N1 90.99(16) 2 8_455 ?
O5 Cu3 O5 177.0(2) 2 . ?
O5 Cu3 O14 91.49(12) 2 . ?
O5 Cu3 O14 91.48(12) . . ?
C7 O3 Cu1 116.3(3) . . ?
C1 O2 Cu2 125.4(3) . . ?
C16 O10 O11B 114.3(5) . . ?
C16 O10 H10 115.4 . . ?
O11B O10 H10 101.2 . . ?
C3 N1 Cu3 118.3(3) . 7_556 ?
C4 N1 Cu3 124.1(3) . 7_556 ?
C4 N1 C3 117.6(4) . . ?
C13 O5 Cu3 116.2(3) . . ?
Cu3 O14 H14A 107(6) . 2 ?
Cu3 O14 H14A 107.1 . . ?
Cu3 O14 H14B 107(6) . 2 ?
Cu3 O14 H14B 107.3 . . ?
H14A O14 H14A 145.7 . 2 ?
H14A O14 H14B 64.9 . 2 ?
H14A O14 H14B 104.5 2 2 ?
H14A O14 H14B 104.5 . . ?
H14B O14 H14A 64.9 . 2 ?
H14B O14 H14B 145.4 . 2 ?
H13A O13 H13B 104.5 . . ?
H16A O16 H16B 104.5 . . ?
H18C O18 H18D 104.5 . . ?
C8 N2 Cu1 117.8(3) . . ?
C12 N2 Cu1 124.0(3) . . ?
C12 N2 C8 118.2(4) . . ?
O3 C7 C6 114.8(5) . . ?
O4 C7 O3 125.5(5) . . ?
O4 C7 C6 119.7(5) . . ?
C2 C6 C7 124.0(4) . . ?
C2 C6 C5 117.5(5) . . ?
C5 C6 C7 118.5(5) . . ?
C6 C2 C1 123.7(4) . . ?
C3 C2 C6 118.8(4) . . ?
C3 C2 C1 117.3(4) . . ?
O2 C1 C2 115.0(4) . . ?
O1 C1 O2 126.0(5) . . ?
O1 C1 C2 118.9(5) . . ?
Cu2 O9 H9 138(2) . . ?
C19 O9 Cu2 108.9(4) . . ?
C19 O9 H9 107.1(19) . . ?
O9 C19 H19 109.2 . . ?
O9 C19 C18 108.6(5) . . ?
O9 C19 C20 110.0(7) . . ?
C18 C19 H19 109.2 . . ?
C20 C19 H19 109.2 . . ?
C20 C19 C18 110.5(6) . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
N3 C18 C19 113.7(5) . . ?
N3 C18 H18A 108.8 . . ?
N3 C18 H18B 108.8 . . ?
C18 N3 Cu2 106.4(4) . . ?
C18 N3 C21 110.4(5) . . ?
C15 N3 Cu2 111.7(4) . . ?
C15 N3 C18 108.7(5) . . ?
C15 N3 C21 111.6(5) . . ?
C21 N3 Cu2 108.0(4) . . ?
N3 C15 H15A 108.7 . . ?
N3 C15 H15B 108.7 . . ?
N3 C15 C16 114.4(5) . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
O10 C16 C15 110.9(5) . . ?
O10 C16 H16 108.3 . . ?
O10 C16 C17 109.8(6) . . ?
C15 C16 H16 108.3 . . ?
C15 C16 C17 111.2(6) . . ?
C17 C16 H16 108.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C21 H21A 109.3 . . ?
N3 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 N3 111.5(6) . . ?
C22 C21 H21A 109.3 . . ?
C22 C21 H21B 109.3 . . ?
C21 C22 H22 105.6 . . ?
C23 C22 C21 112.1(8) . . ?
C23 C22 H22 105.6 . . ?
O11A C22 C21 110.2(8) . . ?
O11A C22 H22 105.6 . . ?
O11A C22 C23 116.7(8) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 O11A Cu2 115.4(6) . . ?
C22 O11A O11B 97.0(9) . . ?
O11B O11A Cu2 53.2(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Cu2 O12 H12A 110.9 . . ?
Cu2 O12 H12B 110.6 . . ?
H12A O12 H12B 103.3 . . ?
N1 C3 C2 123.7(5) . . ?
N1 C3 H3 118.2 . . ?
C2 C3 H3 118.2 . . ?
N1 C4 H4 118.7 . . ?
N1 C4 C5 122.6(5) . . ?
C5 C4 H4 118.7 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.0(5) . . ?
C4 C5 H5 120.0 . . ?
N2 C8 H8 118.0 . . ?
N2 C8 C9 124.1(5) . . ?
C9 C8 H8 118.0 . . ?
C8 C9 C10 118.2(5) . . ?
C8 C9 C14 116.2(5) . . ?
C10 C9 C14 125.3(4) . . ?
C9 C10 C13 124.2(5) . . ?
C11 C10 C9 116.9(5) . . ?
C11 C10 C13 118.9(5) . . ?
O6 C13 O5 125.2(5) . . ?
O6 C13 C10 119.0(5) . . ?
O5 C13 C10 115.8(5) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(5) . . ?
C12 C11 H11 119.8 . . ?
N2 C12 C11 122.2(5) . . ?
N2 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
O8 C14 C9 115.8(5) . . ?
O7 C14 O8 125.5(5) . . ?
O7 C14 C9 118.5(5) . . ?
Cu1 O15 H15C 127.7 . . ?
Cu1 O15 H15D 127.7 . . ?
H15C O15 H15D 104.5 . . ?
Cu2 O11B O10 103.7(4) . . ?
O11A O11B Cu2 78.5(6) . . ?
O11A O11B O10 149.3(7) . . ?
H17D O17 H17E 104.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O3 C7 O4 -4.0(8) . . . . ?
Cu1 O3 C7 C6 174.5(3) . . . . ?
Cu1 N2 C8 C9 178.4(4) . . . . ?
Cu1 N2 C12 C11 -177.6(4) . . . . ?
Cu2 O2 C1 O1 2.8(8) . . . . ?
Cu2 O2 C1 C2 -179.8(3) . . . . ?
Cu2 O9 C19 C18 -22.5(7) . . . . ?
Cu2 O9 C19 C20 -143.6(5) . . . . ?
Cu2 N3 C15 C16 59.0(6) . . . . ?
Cu2 N3 C21 C22 -23.6(8) . . . . ?
Cu2 O11A O11B O10 -97.5(14) . . . . ?
Cu3 N1 C3 C2 179.0(4) 7_556 . . . ?
Cu3 N1 C4 C5 -179.1(4) 7_556 . . . ?
Cu3 O5 C13 O6 5.5(9) . . . . ?
Cu3 O5 C13 C10 -173.3(4) . . . . ?
O3 C7 C6 C2 118.5(6) . . . . ?
O3 C7 C6 C5 -63.6(7) . . . . ?
O2 Cu2 O11B O10 -28.1(7) . . . . ?
O2 Cu2 O11B O11A -176.8(4) . . . . ?
N1 C4 C5 C6 0.7(9) . . . . ?
O4 C7 C6 C2 -62.9(8) . . . . ?
O4 C7 C6 C5 114.9(6) . . . . ?
N2 C8 C9 C10 -1.5(8) . . . . ?
N2 C8 C9 C14 -175.4(5) . . . . ?
C7 C6 C2 C1 -6.1(8) . . . . ?
C7 C6 C2 C3 178.6(5) . . . . ?
C7 C6 C5 C4 -178.9(5) . . . . ?
C6 C2 C1 O2 152.1(5) . . . . ?
C6 C2 C1 O1 -30.4(8) . . . . ?
C6 C2 C3 N1 -0.4(8) . . . . ?
C2 C6 C5 C4 -0.9(8) . . . . ?
C1 C2 C3 N1 -176.0(5) . . . . ?
O9 Cu2 O11B O10 139.9(4) . . . . ?
O9 Cu2 O11B O11A -8.7(8) . . . . ?
O9 C19 C18 N3 49.2(8) . . . . ?
C19 C18 N3 Cu2 -50.6(6) . . . . ?
C19 C18 N3 C15 -171.0(6) . . . . ?
C19 C18 N3 C21 66.3(7) . . . . ?
C18 N3 C15 C16 176.1(5) . . . . ?
C18 N3 C21 C22 -139.5(7) . . . . ?
N3 Cu2 O11B O10 66.6(4) . . . . ?
N3 Cu2 O11B O11A -82.0(5) . . . . ?
N3 C15 C16 O10 -51.5(7) . . . . ?
N3 C15 C16 C17 -174.0(6) . . . . ?
N3 C21 C22 C23 168.6(8) . . . . ?
N3 C21 C22 O11A 36.7(12) . . . . ?
C15 N3 C21 C22 99.5(8) . . . . ?
C16 O10 O11B Cu2 -78.0(6) . . . . ?
C16 O10 O11B O11A 12.5(15) . . . . ?
C21 N3 C15 C16 -62.0(7) . . . . ?
C21 C22 O11A Cu2 -32.7(12) . . . . ?
C21 C22 O11A O11B -85.2(10) . . . . ?
C22 O11A O11B Cu2 116.6(7) . . . . ?
C22 O11A O11B O10 19.1(16) . . . . ?
C23 C22 O11A Cu2 -162.1(8) . . . . ?
C23 C22 O11A O11B 145.4(10) . . . . ?
O11A Cu2 O11B O10 148.6(8) . . . . ?
C20 C19 C18 N3 170.0(6) . . . . ?
O12 Cu2 O11B O10 -119.2(5) . . . . ?
O12 Cu2 O11B O11A 92.2(5) . . . . ?
C3 N1 C4 C5 -0.2(8) . . . . ?
C3 C2 C1 O2 -32.6(7) . . . . ?
C3 C2 C1 O1 145.0(5) . . . . ?
C4 N1 C3 C2 0.1(8) . . . . ?
C5 C6 C2 C1 176.1(5) . . . . ?
C5 C6 C2 C3 0.8(7) . . . . ?
C8 N2 C12 C11 0.5(8) . . . . ?
C8 C9 C10 C13 -179.4(5) . . . . ?
C8 C9 C10 C11 2.2(8) . . . . ?
C8 C9 C14 O8 -48.9(8) . . . . ?
C8 C9 C14 O7 126.7(6) . . . . ?
C9 C10 C13 O6 141.9(7) . . . . ?
C9 C10 C13 O5 -39.3(8) . . . . ?
C9 C10 C11 C12 -1.6(8) . . . . ?
C10 C9 C14 O8 137.6(6) . . . . ?
C10 C9 C14 O7 -46.7(8) . . . . ?
C10 C11 C12 N2 0.3(9) . . . . ?
C13 C10 C11 C12 179.8(5) . . . . ?
C11 C10 C13 O6 -39.7(9) . . . . ?
C11 C10 C13 O5 139.2(6) . . . . ?
C12 N2 C8 C9 0.1(8) . . . . ?
C14 C9 C10 C13 -6.1(9) . . . . ?
C14 C9 C10 C11 175.5(5) . . . . ?
O11B O10 C16 C15 56.1(7) . . . . ?
O11B O10 C16 C17 179.4(6) . . . . ?

_olex2_diffrn_ambient_temperature_device 150
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.857(2)
2 0.143(2)

# start Validation Reply Form
_vrf_DIFMN02_mo_xs_42_2022_0ma   
;
PROBLEM: The minimum difference density is < -0.1*ZMAX*1.00  
RESPONSE: The crystals showed two domains.
So, this is attributed to small twin components (15%) which
is modelled and where overlap from the second twin domain causes
errors in the intensities of some reflections.
;
_vrf_PLAT097_mo_xs_42_2022_0ma   
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       3.73 eA-3  
RESPONSE: The crystals showed two domains as well as
disorder effects in solvent molecules.
;
_vrf_PLAT098_mo_xs_42_2022_0ma   
;
PROBLEM: Large Reported Min.  (Negative) Residual Density      -4.09 eA-3  
RESPONSE: The crystals showed two domains as well as
unmodelled disorder effects in solvent molecules.
;
_vrf_PLAT420_mo_xs_42_2022_0ma   
;
PROBLEM: D-H Bond Without Acceptor  O18      --H18C  
RESPONSE: The crystals showed disorder effects.
Which, in this case, is not not readily interpreted
by the checkcif routine.
;
# end Validation Reply Form
