#------------------------------------------------------------------------------
#$Date: 2025-07-06 18:42:04 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 300919 $
#$URL: svn://www.crystallography.net/cod/cif/7/71/83/7718385.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_7718385
loop_
_publ_author_name
'Gilbert, Ugo'
'Mu, Xiao'
'Lam, Yan Yu Sarah'
'De Leener, Gaël'
'Schoenauen, Martin'
'Bottin, Maëlle'
'Robeyns, Koen'
'Luhmer, Michel'
'Robiette, Raphaël'
'Singleton, Michael L.'
_publ_section_title
;
 Influence of imidazole functionalization on the properties of small
 molecule models of the LPMO active site.
;
_journal_issue                   15
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6174
_journal_page_last               6187
_journal_paper_doi               10.1039/d4dt03424d
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C20 H30 Cl2 Cu2 N10, 2(Cl O4)'
_chemical_formula_sum            'C20 H30 Cl4 Cu2 N10 O8'
_chemical_formula_weight         807.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'dual space'
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-07-10 deposited with the CCDC.	2025-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                80.624(17)
_cell_angle_beta                 73.129(16)
_cell_angle_gamma                69.64(2)
_cell_formula_units_Z            1
_cell_length_a                   7.5005(15)
_cell_length_b                   8.931(2)
_cell_length_c                   12.916(2)
_cell_measurement_reflns_used    2625
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.0990
_cell_measurement_theta_min      2.8300
_cell_volume                     774.4(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       MAR
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method
;
'60 images, ΔΦ 3.0° '
'60 images, ΔΦ 3.0° (2nd orientation)'
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10998
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.203
_diffrn_reflns_theta_min         2.849
_diffrn_source                   'Incoatec microfocus source'
_exptl_absorpt_coefficient_mu    1.779
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_description       plate
_exptl_crystal_F_000             410
_exptl_crystal_recrystallization_method
'diffusion of diethyl ether in a methanol solution of the compound'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3043
_refine_ls_number_restraints     56
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0422
_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)+(0.0601P)²+0.7141P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1130
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2696
_reflns_number_total             3043
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt03424d2.cif
_cod_data_source_block           ms_ug84
_cod_depositor_comments
'Adding full bibliography for 7718380--7718387.cif.'
_cod_database_code               7718385
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.33900(6) 0.47624(4) 0.42991(3) 0.03957(15) Uani 1 1 d . . . . .
Cl2 Cl 0.29609(12) 0.68350(9) 0.52815(7) 0.0458(2) Uani 1 1 d . . . . .
N3 N 0.4310(4) 0.5896(3) 0.2923(2) 0.0478(7) Uani 1 1 d . . . . .
C4 C 0.4190(6) 0.7382(5) 0.2540(3) 0.0547(9) Uani 1 1 d . . . . .
H4 H 0.357651 0.827805 0.294435 0.066 Uiso 1 1 calc R U . . .
N5 N 0.5087(5) 0.7401(4) 0.1483(3) 0.0651(9) Uani 1 1 d . . . . .
H5 H 0.519221 0.823835 0.106733 0.078 Uiso 1 1 calc R U . . .
C6 C 0.5805(7) 0.5873(6) 0.1171(3) 0.0657(11) Uani 1 1 d . . . . .
H6 H 0.648836 0.553957 0.047901 0.079 Uiso 1 1 calc R U . . .
C7 C 0.5323(6) 0.4943(5) 0.2070(3) 0.0521(8) Uani 1 1 d . . . . .
C8 C 0.5606(6) 0.3196(5) 0.2328(3) 0.0553(9) Uani 1 1 d . . . . .
H8A H 0.563904 0.270702 0.170207 0.066 Uiso 1 1 calc R U . . .
H8B H 0.683167 0.266262 0.253600 0.066 Uiso 1 1 calc R U . . .
N9 N 0.3922(4) 0.3064(3) 0.3236(2) 0.0443(6) Uani 1 1 d . . . . .
H9 H 0.277731 0.338859 0.293228 0.053 Uiso 1 1 calc R U . . .
C10 C 0.4169(5) 0.1411(4) 0.3702(3) 0.0498(8) Uani 1 1 d . . . . .
H10A H 0.521901 0.106586 0.406937 0.060 Uiso 1 1 calc R U . . .
H10B H 0.452475 0.070376 0.312749 0.060 Uiso 1 1 calc R U . . .
C11 C 0.2273(6) 0.1315(4) 0.4499(3) 0.0515(8) Uani 1 1 d . . . . .
H11A H 0.120552 0.178853 0.414636 0.062 Uiso 1 1 calc R U . . .
H11B H 0.237578 0.019795 0.469377 0.062 Uiso 1 1 calc R U . . .
C12 C 0.1785(5) 0.2134(4) 0.5503(3) 0.0456(8) Uani 1 1 d . . . . .
N13 N 0.2034(4) 0.3598(3) 0.5516(2) 0.0427(6) Uani 1 1 d . . . . .
C14 C 0.1413(5) 0.3951(4) 0.6546(3) 0.0487(8) Uani 1 1 d . . . . .
H14 H 0.141083 0.487390 0.679254 0.058 Uiso 1 1 calc R U . . .
N15 N 0.0792(4) 0.2805(4) 0.7179(2) 0.0541(8) Uani 1 1 d . . . . .
C16 C 0.1022(5) 0.1652(4) 0.6531(3) 0.0543(9) Uani 1 1 d . . . . .
H16 H 0.071098 0.071011 0.675647 0.065 Uiso 1 1 calc R U . . .
C17 C 0.0024(7) 0.2765(6) 0.8367(3) 0.0743(13) Uani 1 1 d . . . . .
H17A H 0.006161 0.369472 0.863126 0.111 Uiso 1 1 calc R U . . .
H17B H 0.081654 0.181836 0.869015 0.111 Uiso 1 1 calc R U . . .
H17C H -0.130798 0.275470 0.855349 0.111 Uiso 1 1 calc R U . . .
Cl21 Cl 0.8418(5) 0.8108(4) 0.86937(19) 0.0518(9) Uani 0.797(10) 1 d D . P A 1
O22 O 0.6591(11) 0.8955(9) 0.9319(7) 0.157(4) Uani 0.797(10) 1 d D U P A 1
O23 O 0.8408(10) 0.6650(5) 0.8420(5) 0.109(2) Uani 0.797(10) 1 d D . P A 1
O24 O 0.8869(11) 0.9071(7) 0.7751(4) 0.100(2) Uani 0.797(10) 1 d D . P A 1
O25 O 0.9797(11) 0.7757(13) 0.9281(5) 0.152(3) Uani 0.797(10) 1 d D . P A 1
Cl2B Cl 0.849(2) 0.8271(17) 0.8724(12) 0.077(5) Uani 0.203(10) 1 d D U P A 2
O22B O 0.645(2) 0.874(3) 0.898(2) 0.101(8) Uani 0.203(10) 1 d D U P A 2
O23B O 0.929(4) 0.669(2) 0.913(2) 0.137(10) Uani 0.203(10) 1 d D U P A 2
O24B O 0.911(4) 0.832(4) 0.7588(13) 0.129(9) Uani 0.203(10) 1 d D U P A 2
O25B O 0.916(4) 0.924(4) 0.911(2) 0.163(11) Uani 0.203(10) 1 d D U P A 2
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'
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cu1 N13 167.04(12) . . ?
N3 Cu1 N9 80.24(12) . . ?
N13 Cu1 N9 92.32(11) . . ?
N3 Cu1 Cl2 92.26(9) . . ?
N13 Cu1 Cl2 95.13(9) . . ?
N9 Cu1 Cl2 172.49(8) . . ?
C4 N3 C7 106.8(3) . . ?
C4 N3 Cu1 138.2(3) . . ?
C7 N3 Cu1 114.9(2) . . ?
N3 C4 N5 109.5(4) . . ?
N3 C4 H4 125.2 . . ?
N5 C4 H4 125.2 . . ?
C4 N5 C6 108.7(3) . . ?
C4 N5 H5 125.6 . . ?
C6 N5 H5 125.6 . . ?
C7 C6 N5 106.0(4) . . ?
C7 C6 H6 127.0 . . ?
N5 C6 H6 127.0 . . ?
C6 C7 N3 108.9(4) . . ?
C6 C7 C8 135.5(4) . . ?
N3 C7 C8 115.6(3) . . ?
N9 C8 C7 106.6(3) . . ?
N9 C8 H8A 110.4 . . ?
C7 C8 H8A 110.4 . . ?
N9 C8 H8B 110.4 . . ?
C7 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
C10 N9 C8 112.6(3) . . ?
C10 N9 Cu1 116.6(2) . . ?
C8 N9 Cu1 107.3(2) . . ?
C10 N9 H9 106.6 . . ?
C8 N9 H9 106.6 . . ?
Cu1 N9 H9 106.6 . . ?
N9 C10 C11 109.9(3) . . ?
N9 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
N9 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 C10 113.7(3) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C16 C12 N13 108.2(3) . . ?
C16 C12 C11 128.2(3) . . ?
N13 C12 C11 123.6(3) . . ?
C14 N13 C12 106.1(3) . . ?
C14 N13 Cu1 126.4(2) . . ?
C12 N13 Cu1 127.0(2) . . ?
N13 C14 N15 110.8(3) . . ?
N13 C14 H14 124.6 . . ?
N15 C14 H14 124.6 . . ?
C14 N15 C16 107.6(3) . . ?
C14 N15 C17 126.5(4) . . ?
C16 N15 C17 125.9(3) . . ?
C12 C16 N15 107.3(3) . . ?
C12 C16 H16 126.4 . . ?
N15 C16 H16 126.4 . . ?
N15 C17 H17A 109.5 . . ?
N15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O25 Cl21 O22 109.1(6) . . ?
O25 Cl21 O24 111.1(5) . . ?
O22 Cl21 O24 107.6(4) . . ?
O25 Cl21 O23 107.6(5) . . ?
O22 Cl21 O23 111.5(5) . . ?
O24 Cl21 O23 109.9(4) . . ?
O25B Cl2B O22B 112.4(13) . . ?
O25B Cl2B O24B 110.4(13) . . ?
O22B Cl2B O24B 106.0(12) . . ?
O25B Cl2B O23B 108.3(13) . . ?
O22B Cl2B O23B 111.6(13) . . ?
O24B Cl2B O23B 108.0(13) . . ?
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 N3 1.961(3) . ?
Cu1 N13 1.965(3) . ?
Cu1 N9 2.070(3) . ?
Cu1 Cl2 2.2920(10) . ?
N3 C4 1.320(4) . ?
N3 C7 1.374(5) . ?
C4 N5 1.337(5) . ?
C4 H4 0.9300 . ?
N5 C6 1.362(6) . ?
N5 H5 0.8600 . ?
C6 C7 1.349(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.493(5) . ?
C8 N9 1.478(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N9 C10 1.471(4) . ?
N9 H9 0.9800 . ?
C10 C11 1.515(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.482(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C16 1.349(5) . ?
C12 N13 1.387(4) . ?
N13 C14 1.327(4) . ?
C14 N15 1.330(5) . ?
C14 H14 0.9300 . ?
N15 C16 1.365(5) . ?
N15 C17 1.473(5) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
Cl21 O25 1.377(6) . ?
Cl21 O22 1.392(5) . ?
Cl21 O24 1.400(4) . ?
Cl21 O23 1.406(5) . ?
Cl2B O25B 1.362(10) . ?
Cl2B O22B 1.392(9) . ?
Cl2B O24B 1.403(9) . ?
Cl2B O23B 1.405(10) . ?
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
C7 N3 C4 N5 0.0(4) . . . . ?
Cu1 N3 C4 N5 -177.2(3) . . . . ?
N3 C4 N5 C6 0.2(5) . . . . ?
C4 N5 C6 C7 -0.3(5) . . . . ?
N5 C6 C7 N3 0.3(5) . . . . ?
N5 C6 C7 C8 179.2(4) . . . . ?
C4 N3 C7 C6 -0.2(4) . . . . ?
Cu1 N3 C7 C6 177.8(3) . . . . ?
C4 N3 C7 C8 -179.3(3) . . . . ?
Cu1 N3 C7 C8 -1.4(4) . . . . ?
C6 C7 C8 N9 -150.1(5) . . . . ?
N3 C7 C8 N9 28.8(4) . . . . ?
C7 C8 N9 C10 -170.3(3) . . . . ?
C7 C8 N9 Cu1 -40.7(3) . . . . ?
C8 N9 C10 C11 -170.9(3) . . . . ?
Cu1 N9 C10 C11 64.4(3) . . . . ?
N9 C10 C11 C12 -69.3(4) . . . . ?
C10 C11 C12 C16 -140.2(4) . . . . ?
C10 C11 C12 N13 40.9(5) . . . . ?
C16 C12 N13 C14 -0.2(4) . . . . ?
C11 C12 N13 C14 179.0(3) . . . . ?
C16 C12 N13 Cu1 171.6(2) . . . . ?
C11 C12 N13 Cu1 -9.3(5) . . . . ?
C12 N13 C14 N15 0.1(4) . . . . ?
Cu1 N13 C14 N15 -171.8(2) . . . . ?
N13 C14 N15 C16 0.0(4) . . . . ?
N13 C14 N15 C17 179.2(3) . . . . ?
N13 C12 C16 N15 0.2(4) . . . . ?
C11 C12 C16 N15 -178.9(3) . . . . ?
C14 N15 C16 C12 -0.1(4) . . . . ?
C17 N15 C16 C12 -179.3(4) . . . . ?
