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#$Date: 2025-07-06 19:42:04 +0300 (Sun, 06 Jul 2025) $
#$Revision: 300919 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/83/7718381.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_7718381
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 H26 Cl2 Cu2 N10, 2(Cl O4)'
_chemical_formula_sum            'C20 H26 Cl4 Cu2 N10 O8'
_chemical_formula_weight         803.39
_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                106.261(10)
_cell_angle_beta                 90.179(8)
_cell_angle_gamma                109.045(12)
_cell_formula_units_Z            1
_cell_length_a                   7.3349(9)
_cell_length_b                   8.8634(12)
_cell_length_c                   12.9399(12)
_cell_measurement_reflns_used    4960
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.9860
_cell_measurement_theta_min      3.1650
_cell_volume                     759.24(17)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method
;
'200 images, ΔΦ 2.0° '
'45 images, ΔΦ 2.0° (2nd orientation)'
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9645
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.117
_diffrn_reflns_theta_min         2.954
_diffrn_source                   'Incoatec microfocus source'
_exptl_absorpt_coefficient_mu    1.814
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62792
_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    1.757
_exptl_crystal_description       plate
_exptl_crystal_F_000             406
_exptl_crystal_recrystallization_method
'diffusion of diethyl ether in a methanol solution of the compound'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2986
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0371
_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)+(0.0466P)²+0.5033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.0979
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2745
_reflns_number_total             2986
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt03424d2.cif
_cod_data_source_block           ms_ugoS2
_cod_depositor_comments
'Adding full bibliography for 7718380--7718387.cif.'
_cod_original_cell_volume        759.25(16)
_cod_database_code               7718381
_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 0.78751(4) 0.53671(4) 0.50499(3) 0.03728(13) Uani 1 1 d . . . . .
Cl2 Cl 0.83467(9) 0.30515(8) 0.52672(5) 0.04073(17) Uani 1 1 d . . . . .
N3 N 0.7080(3) 0.4294(3) 0.3489(2) 0.0445(5) Uani 1 1 d . . . . .
C4 C 0.6944(4) 0.2917(4) 0.2729(3) 0.0516(7) Uani 1 1 d . . . . .
H4 H 0.717672 0.200152 0.284009 0.062 Uiso 1 1 calc R U . . .
N5 N 0.6420(4) 0.3024(4) 0.1766(2) 0.0641(8) Uani 1 1 d . . . . .
H5 H 0.624289 0.226012 0.115654 0.077 Uiso 1 1 calc R U . . .
C6 C 0.6217(5) 0.4522(6) 0.1907(3) 0.0691(10) Uani 1 1 d . . . . .
H6 H 0.586992 0.492585 0.137474 0.083 Uiso 1 1 calc R U . . .
C7 C 0.6620(4) 0.5324(4) 0.2986(3) 0.0524(7) Uani 1 1 d . . . . .
C8 C 0.6605(4) 0.6896(4) 0.3701(3) 0.0577(8) Uani 1 1 d . . . . .
H8 H 0.630774 0.767381 0.343981 0.069 Uiso 1 1 calc R U . . .
N9 N 0.7019(3) 0.7160(3) 0.4702(2) 0.0490(6) Uani 1 1 d . . . . .
C10 C 0.7001(5) 0.8698(4) 0.5487(3) 0.0612(9) Uani 1 1 d . . . . .
H10A H 0.580886 0.847750 0.583163 0.073 Uiso 1 1 calc R U . . .
H10B H 0.704809 0.952312 0.511978 0.073 Uiso 1 1 calc R U . . .
C11 C 0.8720(5) 0.9375(4) 0.6337(3) 0.0645(10) Uani 1 1 d . . . . .
H11A H 0.990048 0.952475 0.598140 0.077 Uiso 1 1 calc R U . . .
H11B H 0.877053 1.046265 0.679721 0.077 Uiso 1 1 calc R U . . .
C12 C 0.8643(4) 0.8257(4) 0.7026(3) 0.0544(8) Uani 1 1 d . . . . .
N13 N 0.8316(3) 0.6565(3) 0.65908(19) 0.0432(5) Uani 1 1 d . . . . .
C14 C 0.8400(4) 0.5966(4) 0.7410(2) 0.0496(7) Uani 1 1 d . . . . .
H14 H 0.822708 0.485445 0.734240 0.060 Uiso 1 1 calc R U . . .
N15 N 0.8770(4) 0.7183(4) 0.8349(2) 0.0631(8) Uani 1 1 d . . . . .
C16 C 0.8912(5) 0.8616(5) 0.8111(3) 0.0724(11) Uani 1 1 d . . . . .
H16 H 0.915153 0.966130 0.861097 0.087 Uiso 1 1 calc R U . . .
C17 C 0.8981(7) 0.6974(7) 0.9426(3) 0.0923(15) Uani 1 1 d . . . . .
H17A H 1.031040 0.751608 0.972864 0.138 Uiso 1 1 calc R U . . .
H17B H 0.859375 0.580498 0.936306 0.138 Uiso 1 1 calc R U . . .
H17C H 0.817602 0.746517 0.988971 0.138 Uiso 1 1 calc R U . . .
Cl21 Cl 0.44301(17) 0.81714(11) 0.13008(7) 0.0695(3) Uani 1 1 d . . . . .
O22 O 0.482(3) 0.6753(15) 0.0859(16) 0.121(6) Uani 0.486(13) 1 d D . P A 1
O23 O 0.429(2) 0.9050(11) 0.0643(7) 0.140(6) Uani 0.486(13) 1 d D . P A 1
O24 O 0.533(2) 0.9043(10) 0.2290(8) 0.126(6) Uani 0.486(13) 1 d D . P A 1
O25 O 0.2268(15) 0.7466(12) 0.1559(10) 0.123(4) Uani 0.486(13) 1 d D . P A 1
O22B O 0.438(3) 0.6635(17) 0.0585(14) 0.122(6) Uani 0.514(13) 1 d D . P A 2
O23B O 0.3650(17) 0.8977(19) 0.0759(10) 0.136(5) Uani 0.514(13) 1 d D . P A 2
O24B O 0.6530(11) 0.9134(14) 0.1477(16) 0.225(10) Uani 0.514(13) 1 d D . P A 2
O25B O 0.383(3) 0.818(3) 0.2223(9) 0.216(11) Uani 0.514(13) 1 d D . 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'
Cu Cu 0.3201 1.2651 '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'
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
N13 Cu1 N3 170.73(10) . . ?
N13 Cu1 N9 91.62(11) . . ?
N3 Cu1 N9 80.77(11) . . ?
N13 Cu1 Cl2 94.53(8) . . ?
N3 Cu1 Cl2 92.34(7) . . ?
N9 Cu1 Cl2 170.15(8) . . ?
N13 Cu1 Cl2 92.34(7) . 2_766 ?
N3 Cu1 Cl2 93.10(7) . 2_766 ?
N9 Cu1 Cl2 91.18(7) . 2_766 ?
Cl2 Cu1 Cl2 96.25(2) . 2_766 ?
Cu1 Cl2 Cu1 83.75(2) . 2_766 ?
C4 N3 C7 106.6(3) . . ?
C4 N3 Cu1 140.5(2) . . ?
C7 N3 Cu1 112.7(2) . . ?
N3 C4 N5 109.9(3) . . ?
N3 C4 H4 125.0 . . ?
N5 C4 H4 125.0 . . ?
C4 N5 C6 108.9(3) . . ?
C4 N5 H5 125.6 . . ?
C6 N5 H5 125.6 . . ?
N5 C6 C7 106.1(3) . . ?
N5 C6 H6 126.9 . . ?
C7 C6 H6 126.9 . . ?
C6 C7 N3 108.5(3) . . ?
C6 C7 C8 136.2(3) . . ?
N3 C7 C8 115.3(3) . . ?
N9 C8 C7 116.5(3) . . ?
N9 C8 H8 121.8 . . ?
C7 C8 H8 121.8 . . ?
C8 N9 C10 120.4(3) . . ?
C8 N9 Cu1 114.1(2) . . ?
C10 N9 Cu1 125.4(2) . . ?
N9 C10 C11 110.3(2) . . ?
N9 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
N9 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 C10 113.1(3) . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C16 C12 N13 107.2(3) . . ?
C16 C12 C11 130.3(3) . . ?
N13 C12 C11 122.4(3) . . ?
C14 N13 C12 107.0(3) . . ?
C14 N13 Cu1 128.0(2) . . ?
C12 N13 Cu1 125.0(2) . . ?
N13 C14 N15 110.5(3) . . ?
N13 C14 H14 124.8 . . ?
N15 C14 H14 124.8 . . ?
C14 N15 C16 107.1(3) . . ?
C14 N15 C17 125.4(4) . . ?
C16 N15 C17 127.4(3) . . ?
C12 C16 N15 108.2(3) . . ?
C12 C16 H16 125.9 . . ?
N15 C16 H16 125.9 . . ?
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 . . ?
O23 Cl21 O24 116.5(5) . . ?
O23 Cl21 O22 117.0(9) . . ?
O24 Cl21 O22 114.4(9) . . ?
O25B Cl21 O23B 114.1(7) . . ?
O25B Cl21 O22B 118.0(10) . . ?
O23B Cl21 O22B 109.2(8) . . ?
O25B Cl21 O24B 107.8(9) . . ?
O23B Cl21 O24B 104.5(9) . . ?
O22B Cl21 O24B 101.7(8) . . ?
O23 Cl21 O25 102.4(7) . . ?
O24 Cl21 O25 101.1(7) . . ?
O22 Cl21 O25 101.8(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 N13 1.948(2) . ?
Cu1 N3 1.969(2) . ?
Cu1 N9 2.043(2) . ?
Cu1 Cl2 2.2797(7) . ?
Cu1 Cl2 2.7581(8) 2_766 ?
N3 C4 1.309(4) . ?
N3 C7 1.380(4) . ?
C4 N5 1.340(4) . ?
C4 H4 0.9300 . ?
N5 C6 1.346(5) . ?
N5 H5 0.8600 . ?
C6 C7 1.359(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.444(5) . ?
C8 N9 1.268(5) . ?
C8 H8 0.9300 . ?
N9 C10 1.459(4) . ?
C10 C11 1.512(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.496(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C16 1.349(5) . ?
C12 N13 1.384(4) . ?
N13 C14 1.321(4) . ?
C14 N15 1.336(4) . ?
C14 H14 0.9300 . ?
N15 C16 1.361(6) . ?
N15 C17 1.470(5) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
Cl21 O25B 1.274(8) . ?
Cl21 O23 1.329(8) . ?
Cl21 O24 1.333(8) . ?
Cl21 O22 1.349(9) . ?
Cl21 O23B 1.369(9) . ?
Cl21 O22B 1.406(11) . ?
Cl21 O24B 1.478(8) . ?
Cl21 O25 1.578(9) . ?
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(3) . . . . ?
Cu1 N3 C4 N5 -174.6(2) . . . . ?
N3 C4 N5 C6 0.2(4) . . . . ?
C4 N5 C6 C7 -0.4(4) . . . . ?
N5 C6 C7 N3 0.4(4) . . . . ?
N5 C6 C7 C8 -176.6(4) . . . . ?
C4 N3 C7 C6 -0.3(3) . . . . ?
Cu1 N3 C7 C6 176.0(2) . . . . ?
C4 N3 C7 C8 177.5(3) . . . . ?
Cu1 N3 C7 C8 -6.3(3) . . . . ?
C6 C7 C8 N9 177.1(4) . . . . ?
N3 C7 C8 N9 0.2(4) . . . . ?
C7 C8 N9 C10 -178.7(3) . . . . ?
C7 C8 N9 Cu1 5.7(4) . . . . ?
C8 N9 C10 C11 -138.4(3) . . . . ?
Cu1 N9 C10 C11 36.6(4) . . . . ?
N9 C10 C11 C12 -65.6(4) . . . . ?
C10 C11 C12 C16 -132.0(4) . . . . ?
C10 C11 C12 N13 50.3(4) . . . . ?
C16 C12 N13 C14 -0.2(3) . . . . ?
C11 C12 N13 C14 178.0(3) . . . . ?
C16 C12 N13 Cu1 -179.0(2) . . . . ?
C11 C12 N13 Cu1 -0.8(4) . . . . ?
C12 N13 C14 N15 -0.2(3) . . . . ?
Cu1 N13 C14 N15 178.62(19) . . . . ?
N13 C14 N15 C16 0.5(4) . . . . ?
N13 C14 N15 C17 -179.4(3) . . . . ?
N13 C12 C16 N15 0.5(4) . . . . ?
C11 C12 C16 N15 -177.5(3) . . . . ?
C14 N15 C16 C12 -0.6(4) . . . . ?
C17 N15 C16 C12 179.3(3) . . . . ?
