#------------------------------------------------------------------------------
#$Date: 2025-03-04 21:54:08 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298224 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/96/7249643.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7249643
loop_
_publ_author_name
'Mrvoš-Sermek, Draginja'
'Tašner, Marina'
'Vušak, Darko'
'Judaš, Nenad'
'Wzgarda-Raj, Kinga'
'Đilović, Ivica'
'Matković-Čalogović, Dubravka'
_publ_section_title
;
 Robustness and stability of the l-carnosine copper(ii) dimer: changes in
 the copper coordination sphere upon heating/solvent substitution
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              356
_journal_page_last               365
_journal_paper_doi               10.1039/D4CE01070A
_journal_volume                  27
_journal_year                    2025
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C18 H28 Cu2 N8 O8, 2(H2 O)'
_chemical_formula_sum            'C18 H32 Cu2 N8 O10'
_chemical_formula_weight         647.60
_space_group_crystal_system      trigonal
_space_group_IT_number           152
_space_group_name_Hall           'P 31 2"'
_space_group_name_H-M_alt        'P 31 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-03
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-01-22 deposited with the CCDC.	2024-11-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   8.56884(6)
_cell_length_b                   8.56884(6)
_cell_length_c                   30.61946(18)
_cell_measurement_reflns_used    30246
_cell_measurement_temperature    169.98(10)
_cell_measurement_theta_max      74.7530
_cell_measurement_theta_min      4.3220
_cell_volume                     1947.03(2)
_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)'
_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_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
_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_crystal_colour            blue
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_description       'hexagonal plate'
_exptl_crystal_F_000             1002
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_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_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_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0318
_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
_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_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01070a2.cif
_cod_data_source_block           1_170k
_cod_depositor_comments
'Adding full bibliography for 7249643--7249648.cif.'
_cod_original_cell_volume        1947.03(3)
_cod_database_code               7249643
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.761
_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)
;
_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
;
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'
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 . . .
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'
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
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_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_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) . . . . ?
