# Supplementary Information (SI) for Dalton Transactions.
# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ms_ugoS1
_database_code_depnum_ccdc_archive 'CCDC 2369751'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2024-07-10 deposited with the CCDC.	2025-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H22 Cl2 Cu2 N10, 2(Cl O4)'
_chemical_formula_sum            'C18 H22 Cl4 Cu2 N10 O8'
_chemical_formula_weight         775.33

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.2149(9)
_cell_length_b                   8.6311(15)
_cell_length_c                   12.702(2)
_cell_angle_alpha                98.960(15)
_cell_angle_beta                 101.239(14)
_cell_angle_gamma                112.587(15)
_cell_volume                     692.7(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3303
_cell_measurement_theta_min      3.1530
_cell_measurement_theta_max      26.1150

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.859
_exptl_crystal_F_000             390
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.985
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.70219
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?



_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'93 images, ΔΦ 2.0° '
'96 images, ΔΦ 2.0° (2nd orientation)'
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9873
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.151
_diffrn_reflns_theta_max         26.145
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2735
_reflns_number_gt                2568
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       MAR
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     'dual space'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;



_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+0.3753P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2735
_refine_ls_number_parameters     227
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_ref         0.0747
_refine_ls_wR_factor_gt          0.0736
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.27156(4) 0.52212(3) 0.47713(2) 0.03081(10) Uani 1 1 d . . . . .
Cl2 Cl 0.30343(9) 0.27648(6) 0.50302(5) 0.03906(14) Uani 1 1 d . . . . .
N3 N 0.3193(3) 0.6102(2) 0.63580(15) 0.0345(4) Uani 1 1 d . . . . .
C4 C 0.3739(4) 0.5713(3) 0.72961(19) 0.0403(5) Uani 1 1 d . . . . .
H4 H 0.385188 0.469061 0.735555 0.048 Uiso 1 1 calc R U . . .
N5 N 0.4105(3) 0.7012(3) 0.81508(16) 0.0468(5) Uani 1 1 d . . . . .
H5 H 0.446888 0.703119 0.884071 0.056 Uiso 1 1 calc R U . . .
C6 C 0.3809(4) 0.8295(3) 0.7753(2) 0.0468(6) Uani 1 1 d . . . . .
H6 H 0.397778 0.935338 0.816613 0.056 Uiso 1 1 calc R U . . .
C7 C 0.3218(3) 0.7726(3) 0.66339(19) 0.0375(5) Uani 1 1 d . . . . .
C8 C 0.2620(3) 0.8364(3) 0.5695(2) 0.0400(5) Uani 1 1 d . . . . .
H8 H 0.251174 0.941293 0.578445 0.048 Uiso 1 1 calc R U . . .
N9 N 0.2250(3) 0.7403(2) 0.47367(16) 0.0365(4) Uani 1 1 d . . . . .
C10 C 0.1631(4) 0.7926(3) 0.3735(2) 0.0459(6) Uani 1 1 d . . . . .
H10A H 0.202773 0.916506 0.392099 0.055 Uiso 1 1 calc R U . . .
H10B H 0.012383 0.733351 0.342762 0.055 Uiso 1 1 calc R U . . .
C11 C 0.2673(4) 0.7487(3) 0.2877(2) 0.0474(6) Uani 1 1 d . . . . .
H11A H 0.236057 0.795898 0.225514 0.057 Uiso 1 1 calc R U . . .
H11B H 0.417604 0.804419 0.320298 0.057 Uiso 1 1 calc R U . . .
C12 C 0.1997(4) 0.5588(3) 0.24562(19) 0.0407(5) Uani 1 1 d . . . . .
N13 N 0.1909(3) 0.4490(2) 0.31600(15) 0.0362(4) Uani 1 1 d . . . . .
C14 C 0.1310(4) 0.2922(3) 0.2521(2) 0.0412(5) Uani 1 1 d . . . . .
H14 H 0.111875 0.193200 0.277460 0.049 Uiso 1 1 calc R U . . .
N15 N 0.1021(3) 0.2969(3) 0.14629(17) 0.0490(5) Uani 1 1 d . . . . .
H15 H 0.062926 0.209714 0.090602 0.059 Uiso 1 1 calc R U . . .
C16 C 0.1450(4) 0.4637(4) 0.1408(2) 0.0519(6) Uani 1 1 d . . . . .
H16 H 0.137879 0.503708 0.076898 0.062 Uiso 1 1 calc R U . . .
Cl21 Cl 0.76074(10) 0.80004(7) 0.11384(4) 0.04531(16) Uani 1 1 d . . . . .
O22 O 0.789(3) 0.867(2) 0.2297(7) 0.060(4) Uani 0.64(3) 1 d D . P A 1
O23 O 0.5633(19) 0.7929(16) 0.0546(7) 0.077(2) Uani 0.64(3) 1 d D . P A 1
O24 O 0.748(2) 0.6291(12) 0.0968(11) 0.070(2) Uani 0.64(3) 1 d D . P A 1
O25 O 0.919(2) 0.9045(11) 0.0762(13) 0.089(3) Uani 0.64(3) 1 d D . P A 1
O22B O 0.774(5) 0.855(4) 0.2234(14) 0.064(8) Uani 0.36(3) 1 d D U P A 2
O23B O 0.642(5) 0.859(4) 0.0436(11) 0.095(5) Uani 0.36(3) 1 d D U P A 2
O24B O 0.703(4) 0.624(2) 0.076(3) 0.087(6) Uani 0.36(3) 1 d D U P A 2
O25B O 0.976(3) 0.891(3) 0.0984(18) 0.078(4) Uani 0.36(3) 1 d D U P A 2


_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 N13 1.9434(19) . ?
Cu1 N3 1.9517(18) . ?
Cu1 N9 2.0410(18) . ?
Cu1 Cl2 2.2844(7) . ?
N3 C4 1.316(3) . ?
N3 C7 1.383(3) . ?
C4 N5 1.337(3) . ?
C4 H4 0.9300 . ?
N5 C6 1.358(3) . ?
N5 H5 0.8600 . ?
C6 C7 1.352(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.449(3) . ?
C8 N9 1.276(3) . ?
C8 H8 0.9300 . ?
N9 C10 1.462(3) . ?
C10 C11 1.519(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.491(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C16 1.345(3) . ?
C12 N13 1.393(3) . ?
N13 C14 1.323(3) . ?
C14 N15 1.329(3) . ?
C14 H14 0.9300 . ?
N15 C16 1.368(4) . ?
N15 H15 0.8600 . ?
C16 H16 0.9300 . ?
Cl21 O22B 1.371(18) . ?
Cl21 O25 1.376(8) . ?
Cl21 O24B 1.386(17) . ?
Cl21 O23B 1.404(12) . ?
Cl21 O24 1.421(8) . ?
Cl21 O22 1.440(9) . ?
Cl21 O23 1.449(8) . ?
Cl21 O25B 1.513(18) . ?

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 170.87(8) . . ?
N13 Cu1 N9 91.53(8) . . ?
N3 Cu1 N9 80.97(8) . . ?
N13 Cu1 Cl2 95.20(6) . . ?
N3 Cu1 Cl2 91.83(6) . . ?
N9 Cu1 Cl2 171.48(6) . . ?
C4 N3 C7 106.88(19) . . ?
C4 N3 Cu1 139.11(16) . . ?
C7 N3 Cu1 113.47(15) . . ?
N3 C4 N5 109.6(2) . . ?
N3 C4 H4 125.2 . . ?
N5 C4 H4 125.2 . . ?
C4 N5 C6 108.9(2) . . ?
C4 N5 H5 125.5 . . ?
C6 N5 H5 125.5 . . ?
C7 C6 N5 106.2(2) . . ?
C7 C6 H6 126.9 . . ?
N5 C6 H6 126.9 . . ?
C6 C7 N3 108.4(2) . . ?
C6 C7 C8 136.9(2) . . ?
N3 C7 C8 114.73(19) . . ?
N9 C8 C7 116.15(19) . . ?
N9 C8 H8 121.9 . . ?
C7 C8 H8 121.9 . . ?
C8 N9 C10 120.47(19) . . ?
C8 N9 Cu1 114.10(16) . . ?
C10 N9 Cu1 125.39(15) . . ?
N9 C10 C11 110.49(19) . . ?
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 113.5(2) . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C16 C12 N13 108.1(2) . . ?
C16 C12 C11 129.3(2) . . ?
N13 C12 C11 122.6(2) . . ?
C14 N13 C12 106.7(2) . . ?
C14 N13 Cu1 128.03(17) . . ?
C12 N13 Cu1 125.18(15) . . ?
N13 C14 N15 109.9(2) . . ?
N13 C14 H14 125.0 . . ?
N15 C14 H14 125.0 . . ?
C14 N15 C16 108.6(2) . . ?
C14 N15 H15 125.7 . . ?
C16 N15 H15 125.7 . . ?
C12 C16 N15 106.8(2) . . ?
C12 C16 H16 126.6 . . ?
N15 C16 H16 126.6 . . ?
O22B Cl21 O24B 115.3(14) . . ?
O22B Cl21 O23B 112.6(13) . . ?
O24B Cl21 O23B 112.1(10) . . ?
O25 Cl21 O24 110.9(7) . . ?
O25 Cl21 O22 112.0(7) . . ?
O24 Cl21 O22 109.0(6) . . ?
O25 Cl21 O23 109.4(5) . . ?
O24 Cl21 O23 109.0(5) . . ?
O22 Cl21 O23 106.5(7) . . ?
O22B Cl21 O25B 107.9(12) . . ?
O24B Cl21 O25B 105.9(11) . . ?
O23B Cl21 O25B 101.8(12) . . ?

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 170.57(17) . . . . ?
N3 C4 N5 C6 -0.7(3) . . . . ?
C4 N5 C6 C7 1.0(3) . . . . ?
N5 C6 C7 N3 -1.0(3) . . . . ?
N5 C6 C7 C8 178.6(3) . . . . ?
C4 N3 C7 C6 0.6(3) . . . . ?
Cu1 N3 C7 C6 -172.65(16) . . . . ?
C4 N3 C7 C8 -179.07(19) . . . . ?
Cu1 N3 C7 C8 7.7(2) . . . . ?
C6 C7 C8 N9 177.0(3) . . . . ?
N3 C7 C8 N9 -3.4(3) . . . . ?
C7 C8 N9 C10 179.8(2) . . . . ?
C7 C8 N9 Cu1 -2.4(3) . . . . ?
C8 N9 C10 C11 140.4(2) . . . . ?
Cu1 N9 C10 C11 -37.2(3) . . . . ?
N9 C10 C11 C12 64.7(3) . . . . ?
C10 C11 C12 C16 134.9(3) . . . . ?
C10 C11 C12 N13 -47.5(3) . . . . ?
C16 C12 N13 C14 -0.2(3) . . . . ?
C11 C12 N13 C14 -178.3(2) . . . . ?
C16 C12 N13 Cu1 175.94(17) . . . . ?
C11 C12 N13 Cu1 -2.1(3) . . . . ?
C12 N13 C14 N15 0.1(3) . . . . ?
Cu1 N13 C14 N15 -175.92(15) . . . . ?
N13 C14 N15 C16 0.1(3) . . . . ?
N13 C12 C16 N15 0.3(3) . . . . ?
C11 C12 C16 N15 178.1(2) . . . . ?
C14 N15 C16 C12 -0.2(3) . . . . ?

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.061



_exptl_crystal_recrystallization_method 
'diffusion of diethyl ether in a methanol solution of the compound'
####################################################################### 
# 
# 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_ms_ugoS2
_database_code_depnum_ccdc_archive 'CCDC 2369752'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2024-07-10 deposited with the CCDC.	2025-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_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

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.3349(9)
_cell_length_b                   8.8634(12)
_cell_length_c                   12.9399(12)
_cell_angle_alpha                106.261(10)
_cell_angle_beta                 90.179(8)
_cell_angle_gamma                109.045(12)
_cell_volume                     759.25(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4960
_cell_measurement_theta_min      3.1650
_cell_measurement_theta_max      25.9860

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_F_000             406
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.814
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.62792
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?



_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'200 images, ΔΦ 2.0° '
'45 images, ΔΦ 2.0° (2nd orientation)'
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9645
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.954
_diffrn_reflns_theta_max         26.117
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2986
_reflns_number_gt                2745
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       MAR
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     'dual space'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;






_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²+0.5033P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2986
_refine_ls_number_parameters     237
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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


_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 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_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_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) . . . . ?

_refine_diff_density_max         0.434
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.074



_exptl_crystal_recrystallization_method 
'diffusion of diethyl ether in a methanol solution of the compound'
####################################################################### 
# 
# 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_ms_ugd_01_132
_database_code_depnum_ccdc_archive 'CCDC 2369755'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2024-07-10 deposited with the CCDC.	2025-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H19 Cl Cu N5 O5, Cl O4, H2 O'
_chemical_formula_sum            'C11 H21 Cl2 Cu N5 O10'
_chemical_formula_weight         517.77

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.2615(9)
_cell_length_b                   16.4041(17)
_cell_length_c                   16.7373(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1993.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1575
_cell_measurement_theta_min      3.0700
_cell_measurement_theta_max      24.7290

_exptl_crystal_description       'pale blue'
_exptl_crystal_colour            rod
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_F_000             1060
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.424
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.69867
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?



_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'57 images, ΔΦ 2.0° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8064
_diffrn_reflns_av_unetI/netI     0.1005
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.301
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             3518
_reflns_number_gt                2560
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_max     0.932
_reflns_Friedel_fraction_full    0.943

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       MAR
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     'dual space'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;




_refine_special_details          'Refined as a 2-component inversion twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0800P)²+4.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.50(5)
_chemical_absolute_configuration .
_refine_ls_number_reflns         3518
_refine_ls_number_parameters     326
_refine_ls_number_restraints     259
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.0802
_refine_ls_wR_factor_ref         0.1975
_refine_ls_wR_factor_gt          0.1801
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.8286(2) 0.37003(9) 0.77871(9) 0.0393(4) Uani 1 1 d . . . . .
N2 N 0.8324(16) 0.4819(6) 0.7434(6) 0.039(2) Uani 1 1 d . . . . .
C3 C 0.852(2) 0.5276(8) 0.6746(8) 0.048(3) Uani 1 1 d . . . . .
H3 H 0.876018 0.506784 0.624029 0.058 Uiso 1 1 calc R U . . .
C4 C 0.829(3) 0.6064(9) 0.6923(9) 0.062(4) Uani 1 1 d . . . . .
H4 H 0.835287 0.649836 0.656648 0.075 Uiso 1 1 calc R U . . .
N5 N 0.7949(16) 0.6115(7) 0.7738(8) 0.056(3) Uani 1 1 d . . . . .
H5 H 0.777900 0.655323 0.801044 0.067 Uiso 1 1 calc R U . . .
C6 C 0.7935(18) 0.5354(8) 0.8017(8) 0.043(3) Uani 1 1 d . . . . .
C7 C 0.763(3) 0.5069(9) 0.8842(9) 0.061(4) Uani 1 1 d . . . . .
H7A H 0.632841 0.505000 0.896128 0.073 Uiso 1 1 calc R U . . .
H7AB H 0.822668 0.543354 0.921880 0.073 Uiso 1 1 calc R U . . .
N8 N 0.8446(19) 0.4244(6) 0.8896(6) 0.047(3) Uani 1 1 d . . . . .
H8 H 0.976354 0.433605 0.898495 0.056 Uiso 1 1 calc R U . . .
C9 C 0.784(2) 0.3778(9) 0.9575(8) 0.053(4) Uani 1 1 d . . . . .
H9A H 0.653216 0.367779 0.952997 0.064 Uiso 1 1 calc R U . . .
H9AB H 0.805216 0.409217 1.005709 0.064 Uiso 1 1 calc R U . . .
C10 C 0.882(2) 0.2991(9) 0.9642(8) 0.053(4) Uani 1 1 d . . . . .
H10A H 0.859900 0.276412 1.016866 0.063 Uiso 1 1 calc R U . . .
H10B H 1.012862 0.308197 0.958517 0.063 Uiso 1 1 calc R U . . .
C11 C 0.819(2) 0.2381(8) 0.9012(7) 0.045(3) Uani 1 1 d . . . . .
N12 N 0.8043(16) 0.2590(6) 0.8219(6) 0.039(2) Uani 1 1 d . . . . .
C13 C 0.7520(18) 0.1950(8) 0.7826(9) 0.044(3) Uani 1 1 d . . . . .
H13 H 0.735521 0.192664 0.727580 0.053 Uiso 1 1 calc R U . . .
N14 N 0.7253(15) 0.1331(7) 0.8328(7) 0.046(3) Uani 1 1 d . . . . .
C15 C 0.773(2) 0.1594(9) 0.9071(9) 0.051(4) Uani 1 1 d . . . . .
H15 H 0.773700 0.128256 0.953580 0.062 Uiso 1 1 calc R U . . .
C16 C 0.673(3) 0.0491(8) 0.8097(10) 0.065(4) Uani 1 1 d . . . . .
H16A H 0.542301 0.042165 0.816401 0.097 Uiso 1 1 calc R U . . .
H16B H 0.736797 0.010690 0.842875 0.097 Uiso 1 1 calc R U . . .
H16C H 0.704789 0.039869 0.754772 0.097 Uiso 1 1 calc R U . . .
O21 O 0.8391(17) 0.3288(6) 0.6664(5) 0.058(3) Uani 1 1 d . . . . .
H21 H 0.943972 0.301048 0.649719 0.070 Uiso 1 1 calc R U . . .
C22 C 0.684(3) 0.3407(12) 0.6076(10) 0.089(6) Uani 1 1 d . . . . .
H22A H 0.663363 0.397899 0.599833 0.133 Uiso 1 1 calc R U . . .
H22B H 0.574229 0.315766 0.628075 0.133 Uiso 1 1 calc R U . . .
H22C H 0.716379 0.315901 0.557581 0.133 Uiso 1 1 calc R U . . .
Cl31 Cl 0.3345(19) 0.3414(7) 0.7944(7) 0.057(4) Uani 0.670(12) 1 d D U P A 1
O32 O 0.486(2) 0.3937(10) 0.7886(11) 0.055(5) Uani 0.670(12) 1 d D U P A 1
O33 O 0.174(2) 0.3836(10) 0.7723(13) 0.082(6) Uani 0.670(12) 1 d D U P A 1
O34 O 0.316(3) 0.3114(14) 0.8719(9) 0.128(8) Uani 0.670(12) 1 d D U P A 1
O35 O 0.359(3) 0.2758(9) 0.7416(12) 0.102(7) Uani 0.670(12) 1 d D U P A 1
Cl3B Cl 0.320(3) 0.3468(12) 0.8067(11) 0.035(5) Uani 0.330(12) 1 d D U P A 2
O32B O 0.464(5) 0.382(3) 0.763(2) 0.068(13) Uani 0.330(12) 1 d D U P A 2
O33B O 0.160(5) 0.349(3) 0.759(2) 0.088(13) Uani 0.330(12) 1 d D U P A 2
O34B O 0.288(6) 0.384(2) 0.8804(16) 0.103(12) Uani 0.330(12) 1 d D U P A 2
O35B O 0.363(5) 0.2647(14) 0.820(3) 0.082(10) Uani 0.330(12) 1 d D U P A 2
Cl41 Cl 0.7476(18) 0.0838(9) 0.5260(7) 0.068(2) Uani 0.670(12) 1 d . U P A 3
O42 O 0.823(5) 0.1620(17) 0.4955(19) 0.101(5) Uani 0.670(12) 1 d . U P A 3
O43 O 0.713(4) 0.0981(15) 0.6086(12) 0.112(6) Uani 0.670(12) 1 d . U P A 3
O44 O 0.584(4) 0.0724(16) 0.4884(16) 0.112(6) Uani 0.670(12) 1 d . U P A 3
O45 O 0.854(4) 0.0157(13) 0.5101(12) 0.111(5) Uani 0.670(12) 1 d . U P A 3
Cl4B Cl 0.713(4) 0.0915(17) 0.5389(15) 0.068(2) Uani 0.330(12) 1 d D U P A 4
O42B O 0.820(8) 0.144(3) 0.493(3) 0.101(5) Uani 0.330(12) 1 d D U P A 4
O43B O 0.571(5) 0.135(3) 0.576(2) 0.112(6) Uani 0.330(12) 1 d D U P A 4
O44B O 0.643(6) 0.027(2) 0.494(3) 0.112(6) Uani 0.330(12) 1 d D U P A 4
O45B O 0.822(6) 0.059(2) 0.600(2) 0.111(5) Uani 0.330(12) 1 d D U P A 4
O51 O 1.1034(17) 0.2352(8) 0.6024(7) 0.082(4) Uani 1 1 d . . . . .
H51A H 1.050181 0.212655 0.565232 0.123 Uiso 1 1 d R U . . .
H51B H 1.160120 0.272761 0.581348 0.123 Uiso 1 1 d 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 N2 1.928(10) . ?
Cu1 N12 1.967(10) . ?
Cu1 O21 1.999(9) . ?
Cu1 N8 2.063(9) . ?
N2 C6 1.342(16) . ?
N2 C3 1.381(16) . ?
C3 C4 1.337(19) . ?
C3 H3 0.9300 . ?
C4 N5 1.389(19) . ?
C4 H4 0.9300 . ?
N5 C6 1.333(17) . ?
N5 H5 0.8600 . ?
C6 C7 1.47(2) . ?
C7 N8 1.478(18) . ?
C7 H7A 0.9700 . ?
C7 H7AB 0.9700 . ?
N8 C9 1.438(17) . ?
N8 H8 0.9800 . ?
C9 C10 1.47(2) . ?
C9 H9A 0.9700 . ?
C9 H9AB 0.9700 . ?
C10 C11 1.524(19) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C15 1.337(19) . ?
C11 N12 1.375(15) . ?
N12 C13 1.295(16) . ?
C13 N14 1.333(17) . ?
C13 H13 0.9300 . ?
N14 C15 1.362(18) . ?
N14 C16 1.482(17) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O21 C22 1.51(2) . ?
O21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
Cl31 O34 1.394(10) . ?
Cl31 O32 1.396(10) . ?
Cl31 O35 1.403(10) . ?
Cl31 O33 1.408(10) . ?
Cl3B O34B 1.397(11) . ?
Cl3B O35B 1.401(11) . ?
Cl3B O32B 1.401(11) . ?
Cl3B O33B 1.408(11) . ?
Cl41 O44 1.36(3) . ?
Cl41 O45 1.38(3) . ?
Cl41 O43 1.42(2) . ?
Cl41 O42 1.48(2) . ?
Cl4B O44B 1.397(11) . ?
Cl4B O42B 1.399(11) . ?
Cl4B O43B 1.401(11) . ?
Cl4B O45B 1.405(12) . ?
O51 H51A 0.8200 . ?
O51 H51B 0.8200 . ?

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
N2 Cu1 N12 174.2(5) . . ?
N2 Cu1 O21 91.9(4) . . ?
N12 Cu1 O21 92.0(4) . . ?
N2 Cu1 N8 82.1(4) . . ?
N12 Cu1 N8 94.3(4) . . ?
O21 Cu1 N8 172.0(5) . . ?
C6 N2 C3 105.8(11) . . ?
C6 N2 Cu1 113.4(8) . . ?
C3 N2 Cu1 140.6(9) . . ?
C4 C3 N2 109.1(13) . . ?
C4 C3 H3 125.4 . . ?
N2 C3 H3 125.4 . . ?
C3 C4 N5 107.3(13) . . ?
C3 C4 H4 126.4 . . ?
N5 C4 H4 126.4 . . ?
C6 N5 C4 106.8(11) . . ?
C6 N5 H5 126.6 . . ?
C4 N5 H5 126.6 . . ?
N5 C6 N2 110.9(12) . . ?
N5 C6 C7 128.8(13) . . ?
N2 C6 C7 120.3(12) . . ?
C6 C7 N8 106.8(12) . . ?
C6 C7 H7A 110.4 . . ?
N8 C7 H7A 110.4 . . ?
C6 C7 H7AB 110.4 . . ?
N8 C7 H7AB 110.4 . . ?
H7A C7 H7AB 108.6 . . ?
C9 N8 C7 114.5(11) . . ?
C9 N8 Cu1 117.6(8) . . ?
C7 N8 Cu1 108.6(8) . . ?
C9 N8 H8 105.0 . . ?
C7 N8 H8 105.0 . . ?
Cu1 N8 H8 105.0 . . ?
N8 C9 C10 112.4(12) . . ?
N8 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N8 C9 H9AB 109.1 . . ?
C10 C9 H9AB 109.1 . . ?
H9A C9 H9AB 107.9 . . ?
C9 C10 C11 112.2(11) . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C15 C11 N12 107.1(12) . . ?
C15 C11 C10 131.1(12) . . ?
N12 C11 C10 121.8(12) . . ?
C13 N12 C11 108.0(11) . . ?
C13 N12 Cu1 126.2(9) . . ?
C11 N12 Cu1 125.4(9) . . ?
N12 C13 N14 110.0(13) . . ?
N12 C13 H13 125.0 . . ?
N14 C13 H13 125.0 . . ?
C13 N14 C15 107.3(11) . . ?
C13 N14 C16 125.6(12) . . ?
C15 N14 C16 126.8(12) . . ?
C11 C15 N14 107.5(12) . . ?
C11 C15 H15 126.2 . . ?
N14 C15 H15 126.2 . . ?
N14 C16 H16A 109.5 . . ?
N14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 O21 Cu1 122.8(10) . . ?
C22 O21 H21 118.6 . . ?
Cu1 O21 H21 118.6 . . ?
O21 C22 H22A 109.5 . . ?
O21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O34 Cl31 O32 110.9(8) . . ?
O34 Cl31 O35 109.1(8) . . ?
O32 Cl31 O35 109.1(7) . . ?
O34 Cl31 O33 109.9(8) . . ?
O32 Cl31 O33 109.4(7) . . ?
O35 Cl31 O33 108.4(8) . . ?
O34B Cl3B O35B 108.7(17) . . ?
O34B Cl3B O32B 113.4(17) . . ?
O35B Cl3B O32B 108.3(16) . . ?
O34B Cl3B O33B 110.8(17) . . ?
O35B Cl3B O33B 107.2(17) . . ?
O32B Cl3B O33B 108.1(16) . . ?
O44 Cl41 O45 106.7(18) . . ?
O44 Cl41 O43 108.8(19) . . ?
O45 Cl41 O43 114.6(18) . . ?
O44 Cl41 O42 106(2) . . ?
O45 Cl41 O42 115.2(18) . . ?
O43 Cl41 O42 104.8(17) . . ?
O44B Cl4B O42B 112.3(19) . . ?
O44B Cl4B O43B 111.0(18) . . ?
O42B Cl4B O43B 109.7(18) . . ?
O44B Cl4B O45B 107.9(17) . . ?
O42B Cl4B O45B 109.4(19) . . ?
O43B Cl4B O45B 106.4(17) . . ?
H51A O51 H51B 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
C6 N2 C3 C4 1.6(18) . . . . ?
Cu1 N2 C3 C4 176.3(12) . . . . ?
N2 C3 C4 N5 0(2) . . . . ?
C3 C4 N5 C6 -1.5(19) . . . . ?
C4 N5 C6 N2 2.6(17) . . . . ?
C4 N5 C6 C7 180.0(16) . . . . ?
C3 N2 C6 N5 -2.6(16) . . . . ?
Cu1 N2 C6 N5 -178.9(9) . . . . ?
C3 N2 C6 C7 179.8(14) . . . . ?
Cu1 N2 C6 C7 3.4(17) . . . . ?
N5 C6 C7 N8 -158.6(14) . . . . ?
N2 C6 C7 N8 18.6(19) . . . . ?
C6 C7 N8 C9 -163.3(12) . . . . ?
C6 C7 N8 Cu1 -29.6(15) . . . . ?
C7 N8 C9 C10 -174.9(13) . . . . ?
Cu1 N8 C9 C10 55.9(15) . . . . ?
N8 C9 C10 C11 -73.0(15) . . . . ?
C9 C10 C11 C15 -133.9(17) . . . . ?
C9 C10 C11 N12 47.9(19) . . . . ?
C15 C11 N12 C13 0.1(16) . . . . ?
C10 C11 N12 C13 178.6(13) . . . . ?
C15 C11 N12 Cu1 173.0(10) . . . . ?
C10 C11 N12 Cu1 -8.4(19) . . . . ?
C11 N12 C13 N14 1.9(15) . . . . ?
Cu1 N12 C13 N14 -170.9(9) . . . . ?
N12 C13 N14 C15 -3.2(15) . . . . ?
N12 C13 N14 C16 -177.3(13) . . . . ?
N12 C11 C15 N14 -2.0(16) . . . . ?
C10 C11 C15 N14 179.6(15) . . . . ?
C13 N14 C15 C11 3.1(16) . . . . ?
C16 N14 C15 C11 177.2(14) . . . . ?

_refine_diff_density_max         0.946
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.119



_exptl_crystal_recrystallization_method 
'diffusion of diethyl ether in a methanol solution of the compound'
####################################################################### 
# 
# 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_ms_ugd-02-042_150k
_database_code_depnum_ccdc_archive 'CCDC 2369757'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2024-07-10 deposited with the CCDC.	2025-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H20 Cl Cu N4 O5, Cl O4'
_chemical_formula_sum            'C13 H20 Cl2 Cu N4 O9'
_chemical_formula_weight         510.77

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   29.258(2)
_cell_length_b                   7.1874(3)
_cell_length_c                   19.1948(19)
_cell_angle_alpha                90
_cell_angle_beta                 99.360(10)
_cell_angle_gamma                90
_cell_volume                     3982.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3492
_cell_measurement_theta_min      3.0530
_cell_measurement_theta_max      26.0460

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_F_000             2088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.420
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.67010
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'151 images, ΔΦ 1.0° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21207
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.921
_diffrn_reflns_theta_max         26.002
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7701
_reflns_number_gt                6714
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       MAR
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     dual
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;




_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0411P)²+24.5165P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7701
_refine_ls_number_parameters     641
_refine_ls_number_restraints     330
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.1638
_refine_ls_wR_factor_gt          0.1593
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.12255(2) -0.12798(8) 0.40496(3) 0.02350(17) Uani 1 1 d . . . . .
N2 N 0.05439(15) -0.1584(6) 0.4101(2) 0.0265(9) Uani 1 1 d . . . . .
C3 C 0.0437(2) -0.2193(8) 0.4735(3) 0.0339(12) Uani 1 1 d . . . . .
H3 H 0.068286 -0.237943 0.511754 0.041 Uiso 1 1 calc R U . . .
C4 C -0.0011(2) -0.2546(8) 0.4842(3) 0.0393(14) Uani 1 1 d . . . . .
H4 H -0.007088 -0.294963 0.528904 0.047 Uiso 1 1 calc R U . . .
C5 C -0.0368(2) -0.2301(9) 0.4286(3) 0.0433(15) Uani 1 1 d . . . . .
H5 H -0.067846 -0.254491 0.434367 0.052 Uiso 1 1 calc R U . . .
C6 C -0.0268(2) -0.1690(8) 0.3636(3) 0.0372(13) Uani 1 1 d . . . . .
H6 H -0.051105 -0.151864 0.324834 0.045 Uiso 1 1 calc R U . . .
C7 C 0.01911(19) -0.1331(7) 0.3559(3) 0.0304(11) Uani 1 1 d . . . . .
C8 C 0.02998(19) -0.0655(7) 0.2853(3) 0.0300(11) Uani 1 1 d . . . . .
H8A H 0.039177 0.067047 0.290156 0.036 Uiso 1 1 calc R U . . .
H8AB H 0.001343 -0.072628 0.249983 0.036 Uiso 1 1 calc R U . . .
C9 C 0.06832(18) -0.1736(8) 0.2571(3) 0.0301(11) Uani 1 1 d . . . . .
H9A H 0.063434 -0.309011 0.261914 0.036 Uiso 1 1 calc R U . . .
H9AB H 0.067480 -0.145233 0.206419 0.036 Uiso 1 1 calc R U . . .
N10 N 0.11371(14) -0.1196(6) 0.2976(2) 0.0259(9) Uani 1 1 d . . . . .
H10 H 0.117868 0.014007 0.285559 0.031 Uiso 1 1 calc R U . . .
C11 C 0.15334(18) -0.2218(7) 0.2725(3) 0.0282(11) Uani 1 1 d . . . . .
H11A H 0.146539 -0.356432 0.267208 0.034 Uiso 1 1 calc R U . . .
H11B H 0.158994 -0.171811 0.226594 0.034 Uiso 1 1 calc R U . . .
C12 C 0.19402(18) -0.1886(6) 0.3285(3) 0.0269(11) Uani 1 1 d . . . . .
N13 N 0.23984(16) -0.2081(6) 0.3250(2) 0.0316(10) Uani 1 1 d . . . . .
C14 C 0.2639(2) -0.1686(7) 0.3916(3) 0.0351(13) Uani 1 1 d . . . . .
H14 H 0.296533 -0.169894 0.405530 0.042 Uiso 1 1 calc R U . . .
C15 C 0.23201(19) -0.1280(7) 0.4332(3) 0.0322(12) Uani 1 1 d . . . . .
H15 H 0.238666 -0.095243 0.481774 0.039 Uiso 1 1 calc R U . . .
N16 N 0.18813(15) -0.1418(6) 0.3935(2) 0.0280(9) Uani 1 1 d . . . . .
C17 C 0.2598(2) -0.2544(8) 0.2613(3) 0.0391(14) Uani 1 1 d . . . . .
H17A H 0.292650 -0.285740 0.274967 0.059 Uiso 1 1 calc R U . . .
H17B H 0.256783 -0.147186 0.229339 0.059 Uiso 1 1 calc R U . . .
H17C H 0.243285 -0.361008 0.237335 0.059 Uiso 1 1 calc R U . . .
O18 O 0.14075(15) -0.1020(5) 0.5117(2) 0.0340(9) Uani 1 1 d . . . . .
H18 H 0.143(2) 0.001(10) 0.525(4) 0.051 Uiso 1 1 d . U . . .
C19 C 0.1634(2) -0.2406(8) 0.5609(3) 0.0403(14) Uani 1 1 d . . . . .
H19A H 0.151856 -0.230135 0.605921 0.060 Uiso 1 1 calc R U . . .
H19B H 0.196938 -0.219787 0.568732 0.060 Uiso 1 1 calc R U . . .
H19C H 0.156622 -0.365287 0.541234 0.060 Uiso 1 1 calc R U . . .
Cu21 Cu 0.37671(2) 0.28481(9) 0.34774(3) 0.02885(18) Uani 1 1 d . . . . .
N22 N 0.44493(17) 0.3085(6) 0.3419(3) 0.0367(11) Uani 1 1 d . . . . .
C23 C 0.4568(2) 0.3670(8) 0.2797(4) 0.0437(15) Uani 1 1 d . . . . .
H23 H 0.432499 0.400324 0.242637 0.052 Uiso 1 1 calc R U . . .
C24 C 0.5020(2) 0.3809(9) 0.2670(5) 0.058(2) Uani 1 1 d . . . . .
H24 H 0.508556 0.424190 0.222948 0.069 Uiso 1 1 calc R U . . .
C25 C 0.5374(3) 0.3293(11) 0.3210(6) 0.071(3) Uani 1 1 d . . . . .
H25 H 0.568748 0.332114 0.313801 0.085 Uiso 1 1 calc R U . . .
C26 C 0.5266(3) 0.2746(10) 0.3847(5) 0.064(2) Uani 1 1 d . . . . .
H26 H 0.550734 0.242732 0.422133 0.077 Uiso 1 1 calc R U . . .
C27 C 0.4800(2) 0.2647(8) 0.3954(4) 0.0466(17) Uani 1 1 d . . . . .
C28 C 0.4686(2) 0.2074(8) 0.4664(4) 0.0527(19) Uani 1 1 d . . . . .
H28A H 0.458442 0.075889 0.463166 0.063 Uiso 1 1 calc R U . . .
H28B H 0.497487 0.213156 0.501391 0.063 Uiso 1 1 calc R U . . .
C29 C 0.4320(2) 0.3204(9) 0.4944(3) 0.0477(17) Uani 1 1 d . . . . .
H29A H 0.433645 0.297720 0.545639 0.057 Uiso 1 1 calc R U . . .
H29B H 0.437157 0.454730 0.487237 0.057 Uiso 1 1 calc R U . . .
N30 N 0.38528(18) 0.2634(7) 0.4554(2) 0.0371(11) Uani 1 1 d . . . . .
H30 H 0.382003 0.128148 0.465769 0.044 Uiso 1 1 calc R U . . .
C31 C 0.3469(2) 0.3572(8) 0.4818(3) 0.0402(14) Uani 1 1 d . . . . .
H31A H 0.353535 0.491575 0.488906 0.048 Uiso 1 1 calc R U . . .
H31B H 0.341842 0.302204 0.527164 0.048 Uiso 1 1 calc R U . . .
C32 C 0.3051(2) 0.3281(7) 0.4258(3) 0.0312(12) Uani 1 1 d . . . . .
N33 N 0.25968(18) 0.3427(6) 0.4299(3) 0.0380(11) Uani 1 1 d . . . . .
C34 C 0.2356(2) 0.3129(7) 0.3618(3) 0.0350(13) Uani 1 1 d . . . . .
H34 H 0.202926 0.315845 0.348005 0.042 Uiso 1 1 calc R U . . .
C35 C 0.26722(18) 0.2789(8) 0.3191(3) 0.0320(12) Uani 1 1 d . . . . .
H35 H 0.260520 0.252382 0.269981 0.038 Uiso 1 1 calc R U . . .
N36 N 0.31073(15) 0.2895(6) 0.3590(2) 0.0283(9) Uani 1 1 d . . . . .
C37 C 0.2398(3) 0.3799(10) 0.4949(4) 0.0515(17) Uani 1 1 d . . . . .
H37A H 0.205887 0.379137 0.483560 0.077 Uiso 1 1 calc R U . . .
H37B H 0.250304 0.501835 0.514010 0.077 Uiso 1 1 calc R U . . .
H37C H 0.250000 0.283377 0.530044 0.077 Uiso 1 1 calc R U . . .
O38 O 0.35602(15) 0.2852(6) 0.2413(2) 0.0373(9) Uani 1 1 d . . . . .
H38 H 0.351(3) 0.392(11) 0.226(4) 0.056 Uiso 1 1 d . U . . .
C39 C 0.3456(3) 0.1345(9) 0.1936(4) 0.0511(17) Uani 1 1 d . . . . .
H39A H 0.315432 0.155675 0.164117 0.077 Uiso 1 1 calc R U . . .
H39B H 0.344646 0.018652 0.220229 0.077 Uiso 1 1 calc R U . . .
H39C H 0.369553 0.125280 0.163525 0.077 Uiso 1 1 calc R U . . .
Cl41 Cl 0.16975(5) 0.27222(17) 0.65075(6) 0.0301(3) Uani 1 1 d D . . . .
O42 O 0.13205(15) 0.3661(6) 0.6768(2) 0.0495(11) Uani 1 1 d D . . . .
O43 O 0.15633(14) 0.2403(5) 0.57527(17) 0.0347(9) Uani 1 1 d D . . . .
O44 O 0.20969(14) 0.3923(6) 0.6618(2) 0.0494(11) Uani 1 1 d D . . . .
O45 O 0.17954(19) 0.0981(6) 0.6863(2) 0.0585(13) Uani 1 1 d D . . . .
Cl51 Cl 0.09808(10) 0.3656(4) 0.37929(16) 0.0237(4) Uani 0.922(7) 1 d D . P A 5
O52 O 0.1254(2) 0.5230(7) 0.4094(4) 0.0372(11) Uani 0.922(7) 1 d D . P A 5
O53 O 0.04950(14) 0.4063(6) 0.3732(3) 0.0426(13) Uani 0.922(7) 1 d D . P A 5
O54 O 0.10857(19) 0.3268(7) 0.3093(2) 0.0402(12) Uani 0.922(7) 1 d D . P A 5
O55 O 0.1095(2) 0.2057(5) 0.4238(2) 0.0467(15) Uani 0.922(7) 1 d D . P A 5
Cl5B Cl 0.1039(12) 0.360(4) 0.3825(19) 0.0237(4) Uani 0.078(7) 1 d D . P A 6
O52B O 0.132(2) 0.518(7) 0.410(4) 0.0372(11) Uani 0.078(7) 1 d D . P A 6
O53B O 0.0637(16) 0.346(7) 0.416(3) 0.0426(13) Uani 0.078(7) 1 d D . P A 6
O54B O 0.090(2) 0.386(8) 0.308(2) 0.0402(12) Uani 0.078(7) 1 d D . P A 6
O55B O 0.1308(17) 0.193(6) 0.394(3) 0.0467(15) Uani 0.078(7) 1 d D . P A 6
Cl61 Cl 0.40306(16) 0.7819(5) 0.3726(3) 0.0264(9) Uani 0.743(8) 1 d D . P B 1
O62 O 0.3751(3) 0.6278(10) 0.3416(6) 0.051(3) Uani 0.743(8) 1 d D . P B 1
O63 O 0.3918(2) 0.8203(8) 0.4418(3) 0.0459(17) Uani 0.743(8) 1 d D . P B 1
O64 O 0.45130(16) 0.7364(8) 0.3789(3) 0.0430(17) Uani 0.743(8) 1 d D . P B 1
O65 O 0.3935(3) 0.9429(7) 0.3280(3) 0.053(2) Uani 0.743(8) 1 d D . P B 1
Cl6B Cl 0.3965(5) 0.7867(17) 0.3615(7) 0.038(4) Uani 0.257(8) 1 d D U P B 2
O62B O 0.3663(8) 0.628(3) 0.3434(15) 0.045(7) Uani 0.257(8) 1 d D U P B 2
O63B O 0.4257(7) 0.753(3) 0.4282(10) 0.081(8) Uani 0.257(8) 1 d D U P B 2
O64B O 0.4247(7) 0.812(3) 0.3078(11) 0.088(8) Uani 0.257(8) 1 d D U P B 2
O65B O 0.3694(4) 0.9512(16) 0.3650(7) 0.027(3) Uani 0.257(8) 1 d D U P B 2
Cl71 Cl 0.3428(2) 0.5999(9) 0.0995(4) 0.0310(13) Uani 0.491(16) 1 d D U P C 3
O72 O 0.3856(3) 0.4967(11) 0.1025(7) 0.052(3) Uani 0.491(16) 1 d D U P C 3
O73 O 0.3496(5) 0.7914(10) 0.0838(7) 0.058(4) Uani 0.491(16) 1 d D U P C 3
O74 O 0.3101(5) 0.5158(18) 0.0456(9) 0.104(6) Uani 0.491(16) 1 d D U P C 3
O75 O 0.3264(7) 0.585(2) 0.1654(7) 0.099(6) Uani 0.491(16) 1 d D U P C 3
Cl7B Cl 0.3306(4) 0.6190(12) 0.1010(4) 0.053(2) Uani 0.509(16) 1 d D U P C 4
O72B O 0.3522(4) 0.6266(14) 0.1747(5) 0.048(3) Uani 0.509(16) 1 d D U P C 4
O73B O 0.3180(8) 0.8021(14) 0.0772(8) 0.121(6) Uani 0.509(16) 1 d D U P C 4
O74B O 0.3641(7) 0.539(3) 0.0625(11) 0.160(8) Uani 0.509(16) 1 d D U P C 4
O75B O 0.2916(4) 0.4983(16) 0.0924(7) 0.078(4) Uani 0.509(16) 1 d D U P C 4


_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 N16 1.969(4) . ?
Cu1 N2 2.024(4) . ?
Cu1 N10 2.035(4) . ?
Cu1 O18 2.040(4) . ?
Cu1 O55B 2.33(5) . ?
N2 C7 1.353(7) . ?
N2 C3 1.377(7) . ?
C3 C4 1.381(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.399(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.520(7) . ?
C8 C9 1.534(7) . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 N10 1.478(6) . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
N10 C11 1.516(7) . ?
N10 H10 1.0000 . ?
C11 C12 1.487(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N16 1.331(7) . ?
C12 N13 1.360(7) . ?
N13 C14 1.385(7) . ?
N13 C17 1.476(7) . ?
C14 C15 1.354(8) . ?
C14 H14 0.9500 . ?
C15 N16 1.386(7) . ?
C15 H15 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O18 C19 1.456(6) . ?
O18 H18 0.79(7) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
Cu21 N36 1.977(4) . ?
Cu21 N22 2.024(5) . ?
Cu21 O38 2.034(4) . ?
Cu21 N30 2.046(5) . ?
Cu21 O65B 2.435(12) 1_545 ?
N22 C23 1.363(8) . ?
N22 C27 1.365(7) . ?
C23 C24 1.387(9) . ?
C23 H23 0.9500 . ?
C24 C25 1.392(12) . ?
C24 H24 0.9500 . ?
C25 C26 1.369(12) . ?
C25 H25 0.9500 . ?
C26 C27 1.413(11) . ?
C26 H26 0.9500 . ?
C27 C28 1.511(10) . ?
C28 C29 1.511(10) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 N30 1.505(7) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
N30 C31 1.468(8) . ?
N30 H30 1.0000 . ?
C31 C32 1.505(8) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 N36 1.347(7) . ?
C32 N33 1.350(7) . ?
N33 C34 1.396(8) . ?
N33 C37 1.484(7) . ?
C34 C35 1.355(8) . ?
C34 H34 0.9500 . ?
C35 N36 1.377(7) . ?
C35 H35 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
O38 C39 1.419(7) . ?
O38 H38 0.83(8) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
Cl41 O45 1.432(4) . ?
Cl41 O44 1.440(4) . ?
Cl41 O42 1.450(4) . ?
Cl41 O43 1.456(3) . ?
Cl51 O53 1.437(4) . ?
Cl51 O55 1.439(4) . ?
Cl51 O52 1.449(4) . ?
Cl51 O54 1.453(4) . ?
Cl5B O55B 1.432(8) . ?
Cl5B O53B 1.437(8) . ?
Cl5B O54B 1.439(8) . ?
Cl5B O52B 1.449(8) . ?
Cl61 O64 1.435(5) . ?
Cl61 O65 1.439(5) . ?
Cl61 O62 1.446(5) . ?
Cl61 O63 1.446(5) . ?
Cl6B O65B 1.431(8) . ?
Cl6B O64B 1.434(8) . ?
Cl6B O63B 1.440(8) . ?
Cl6B O62B 1.448(7) . ?
Cl71 O74 1.426(7) . ?
Cl71 O75 1.429(7) . ?
Cl71 O73 1.430(6) . ?
Cl71 O72 1.447(7) . ?
Cl7B O75B 1.421(7) . ?
Cl7B O73B 1.422(7) . ?
Cl7B O74B 1.439(7) . ?
Cl7B O72B 1.454(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N16 Cu1 N2 170.24(17) . . ?
N16 Cu1 N10 81.63(17) . . ?
N2 Cu1 N10 95.06(17) . . ?
N16 Cu1 O18 90.95(18) . . ?
N2 Cu1 O18 93.41(17) . . ?
N10 Cu1 O18 169.58(17) . . ?
N16 Cu1 O55B 85.5(12) . . ?
N2 Cu1 O55B 103.2(12) . . ?
N10 Cu1 O55B 82.8(13) . . ?
O18 Cu1 O55B 89.3(13) . . ?
C7 N2 C3 117.9(5) . . ?
C7 N2 Cu1 125.6(4) . . ?
C3 N2 Cu1 116.4(4) . . ?
N2 C3 C4 123.1(5) . . ?
N2 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
C5 C4 C3 118.7(6) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 119.3(6) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C7 119.7(6) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
N2 C7 C6 121.3(5) . . ?
N2 C7 C8 118.9(5) . . ?
C6 C7 C8 119.8(5) . . ?
C7 C8 C9 115.1(4) . . ?
C7 C8 H8A 108.5 . . ?
C9 C8 H8A 108.5 . . ?
C7 C8 H8AB 108.5 . . ?
C9 C8 H8AB 108.5 . . ?
H8A C8 H8AB 107.5 . . ?
N10 C9 C8 109.1(4) . . ?
N10 C9 H9A 109.9 . . ?
C8 C9 H9A 109.9 . . ?
N10 C9 H9AB 109.9 . . ?
C8 C9 H9AB 109.9 . . ?
H9A C9 H9AB 108.3 . . ?
C9 N10 C11 111.9(4) . . ?
C9 N10 Cu1 118.7(3) . . ?
C11 N10 Cu1 109.3(3) . . ?
C9 N10 H10 105.2 . . ?
C11 N10 H10 105.2 . . ?
Cu1 N10 H10 105.2 . . ?
C12 C11 N10 104.8(4) . . ?
C12 C11 H11A 110.8 . . ?
N10 C11 H11A 110.8 . . ?
C12 C11 H11B 110.8 . . ?
N10 C11 H11B 110.8 . . ?
H11A C11 H11B 108.9 . . ?
N16 C12 N13 110.6(5) . . ?
N16 C12 C11 120.5(5) . . ?
N13 C12 C11 128.8(5) . . ?
C12 N13 C14 106.8(5) . . ?
C12 N13 C17 126.2(5) . . ?
C14 N13 C17 127.0(5) . . ?
C15 C14 N13 107.1(5) . . ?
C15 C14 H14 126.4 . . ?
N13 C14 H14 126.4 . . ?
C14 C15 N16 109.0(5) . . ?
C14 C15 H15 125.5 . . ?
N16 C15 H15 125.5 . . ?
C12 N16 C15 106.5(4) . . ?
C12 N16 Cu1 113.2(3) . . ?
C15 N16 Cu1 140.1(4) . . ?
N13 C17 H17A 109.5 . . ?
N13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 O18 Cu1 127.3(3) . . ?
C19 O18 H18 115(5) . . ?
Cu1 O18 H18 115(5) . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N36 Cu21 N22 173.44(19) . . ?
N36 Cu21 O38 88.47(18) . . ?
N22 Cu21 O38 94.6(2) . . ?
N36 Cu21 N30 81.51(19) . . ?
N22 Cu21 N30 95.9(2) . . ?
O38 Cu21 N30 169.04(19) . . ?
N36 Cu21 O65B 83.8(3) . 1_545 ?
N22 Cu21 O65B 101.5(3) . 1_545 ?
O38 Cu21 O65B 96.9(4) . 1_545 ?
N30 Cu21 O65B 77.7(4) . 1_545 ?
C23 N22 C27 117.6(6) . . ?
C23 N22 Cu21 117.9(4) . . ?
C27 N22 Cu21 124.5(5) . . ?
N22 C23 C24 124.1(7) . . ?
N22 C23 H23 117.9 . . ?
C24 C23 H23 117.9 . . ?
C23 C24 C25 117.8(8) . . ?
C23 C24 H24 121.1 . . ?
C25 C24 H24 121.1 . . ?
C26 C25 C24 119.3(7) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C25 C26 C27 120.9(7) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
N22 C27 C26 120.2(7) . . ?
N22 C27 C28 119.5(6) . . ?
C26 C27 C28 120.3(6) . . ?
C29 C28 C27 116.5(5) . . ?
C29 C28 H28A 108.2 . . ?
C27 C28 H28A 108.2 . . ?
C29 C28 H28B 108.2 . . ?
C27 C28 H28B 108.2 . . ?
H28A C28 H28B 107.3 . . ?
N30 C29 C28 108.4(5) . . ?
N30 C29 H29A 110.0 . . ?
C28 C29 H29A 110.0 . . ?
N30 C29 H29B 110.0 . . ?
C28 C29 H29B 110.0 . . ?
H29A C29 H29B 108.4 . . ?
C31 N30 C29 112.8(5) . . ?
C31 N30 Cu21 109.8(4) . . ?
C29 N30 Cu21 115.7(4) . . ?
C31 N30 H30 105.9 . . ?
C29 N30 H30 105.9 . . ?
Cu21 N30 H30 105.9 . . ?
N30 C31 C32 105.5(5) . . ?
N30 C31 H31A 110.6 . . ?
C32 C31 H31A 110.6 . . ?
N30 C31 H31B 110.6 . . ?
C32 C31 H31B 110.6 . . ?
H31A C31 H31B 108.8 . . ?
N36 C32 N33 110.2(5) . . ?
N36 C32 C31 119.9(5) . . ?
N33 C32 C31 129.9(5) . . ?
C32 N33 C34 106.6(5) . . ?
C32 N33 C37 126.0(5) . . ?
C34 N33 C37 127.4(5) . . ?
C35 C34 N33 107.7(5) . . ?
C35 C34 H34 126.1 . . ?
N33 C34 H34 126.1 . . ?
C34 C35 N36 108.3(5) . . ?
C34 C35 H35 125.9 . . ?
N36 C35 H35 125.9 . . ?
C32 N36 C35 107.3(5) . . ?
C32 N36 Cu21 112.3(4) . . ?
C35 N36 Cu21 140.2(4) . . ?
N33 C37 H37A 109.5 . . ?
N33 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
N33 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C39 O38 Cu21 130.2(4) . . ?
C39 O38 H38 118(5) . . ?
Cu21 O38 H38 112(5) . . ?
O38 C39 H39A 109.5 . . ?
O38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
O38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
O45 Cl41 O44 111.0(3) . . ?
O45 Cl41 O42 110.3(3) . . ?
O44 Cl41 O42 108.4(3) . . ?
O45 Cl41 O43 109.7(3) . . ?
O44 Cl41 O43 108.8(2) . . ?
O42 Cl41 O43 108.6(3) . . ?
O53 Cl51 O55 110.0(4) . . ?
O53 Cl51 O52 110.3(3) . . ?
O55 Cl51 O52 109.1(3) . . ?
O53 Cl51 O54 108.6(3) . . ?
O55 Cl51 O54 109.4(3) . . ?
O52 Cl51 O54 109.5(3) . . ?
O55B Cl5B O53B 110.3(11) . . ?
O55B Cl5B O54B 108.8(11) . . ?
O53B Cl5B O54B 109.8(11) . . ?
O55B Cl5B O52B 110.0(11) . . ?
O53B Cl5B O52B 109.6(11) . . ?
O54B Cl5B O52B 108.5(11) . . ?
Cl5B O55B Cu1 141(3) . . ?
O64 Cl61 O65 109.1(5) . . ?
O64 Cl61 O62 110.0(5) . . ?
O65 Cl61 O62 109.2(5) . . ?
O64 Cl61 O63 109.6(5) . . ?
O65 Cl61 O63 109.9(4) . . ?
O62 Cl61 O63 109.0(5) . . ?
O65B Cl6B O64B 108.6(9) . . ?
O65B Cl6B O63B 110.5(10) . . ?
O64B Cl6B O63B 109.4(10) . . ?
O65B Cl6B O62B 109.9(10) . . ?
O64B Cl6B O62B 109.0(10) . . ?
O63B Cl6B O62B 109.4(10) . . ?
O74 Cl71 O75 109.2(9) . . ?
O74 Cl71 O73 110.7(7) . . ?
O75 Cl71 O73 109.8(7) . . ?
O74 Cl71 O72 106.6(7) . . ?
O75 Cl71 O72 109.8(7) . . ?
O73 Cl71 O72 110.7(6) . . ?
O75B Cl7B O73B 111.5(8) . . ?
O75B Cl7B O74B 107.3(8) . . ?
O73B Cl7B O74B 111.5(9) . . ?
O75B Cl7B O72B 110.5(7) . . ?
O73B Cl7B O72B 109.0(7) . . ?
O74B Cl7B O72B 106.9(8) . . ?

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 N2 C3 C4 -0.3(8) . . . . ?
Cu1 N2 C3 C4 -177.0(4) . . . . ?
N2 C3 C4 C5 0.8(9) . . . . ?
C3 C4 C5 C6 -0.6(9) . . . . ?
C4 C5 C6 C7 -0.2(9) . . . . ?
C3 N2 C7 C6 -0.5(7) . . . . ?
Cu1 N2 C7 C6 175.9(4) . . . . ?
C3 N2 C7 C8 179.8(4) . . . . ?
Cu1 N2 C7 C8 -3.7(6) . . . . ?
C5 C6 C7 N2 0.7(8) . . . . ?
C5 C6 C7 C8 -179.6(5) . . . . ?
N2 C7 C8 C9 49.9(6) . . . . ?
C6 C7 C8 C9 -129.8(5) . . . . ?
C7 C8 C9 N10 -74.9(6) . . . . ?
C8 C9 N10 C11 179.9(4) . . . . ?
C8 C9 N10 Cu1 51.1(5) . . . . ?
C9 N10 C11 C12 -166.5(4) . . . . ?
Cu1 N10 C11 C12 -32.9(4) . . . . ?
N10 C11 C12 N16 21.8(6) . . . . ?
N10 C11 C12 N13 -162.0(5) . . . . ?
N16 C12 N13 C14 -0.8(6) . . . . ?
C11 C12 N13 C14 -177.4(5) . . . . ?
N16 C12 N13 C17 -178.4(5) . . . . ?
C11 C12 N13 C17 5.1(8) . . . . ?
C12 N13 C14 C15 0.4(6) . . . . ?
C17 N13 C14 C15 177.9(5) . . . . ?
N13 C14 C15 N16 0.1(6) . . . . ?
N13 C12 N16 C15 0.9(5) . . . . ?
C11 C12 N16 C15 177.8(4) . . . . ?
N13 C12 N16 Cu1 -175.9(3) . . . . ?
C11 C12 N16 Cu1 1.0(6) . . . . ?
C14 C15 N16 C12 -0.6(6) . . . . ?
C14 C15 N16 Cu1 174.8(4) . . . . ?
C27 N22 C23 C24 1.4(9) . . . . ?
Cu21 N22 C23 C24 -176.7(5) . . . . ?
N22 C23 C24 C25 0.9(10) . . . . ?
C23 C24 C25 C26 -2.5(11) . . . . ?
C24 C25 C26 C27 1.8(11) . . . . ?
C23 N22 C27 C26 -2.1(8) . . . . ?
Cu21 N22 C27 C26 175.9(4) . . . . ?
C23 N22 C27 C28 177.3(5) . . . . ?
Cu21 N22 C27 C28 -4.7(7) . . . . ?
C25 C26 C27 N22 0.6(10) . . . . ?
C25 C26 C27 C28 -178.9(6) . . . . ?
N22 C27 C28 C29 -43.4(8) . . . . ?
C26 C27 C28 C29 136.0(6) . . . . ?
C27 C28 C29 N30 76.4(7) . . . . ?
C28 C29 N30 C31 176.4(5) . . . . ?
C28 C29 N30 Cu21 -56.0(6) . . . . ?
C29 N30 C31 C32 164.5(5) . . . . ?
Cu21 N30 C31 C32 33.8(5) . . . . ?
N30 C31 C32 N36 -22.2(7) . . . . ?
N30 C31 C32 N33 161.3(5) . . . . ?
N36 C32 N33 C34 -0.4(6) . . . . ?
C31 C32 N33 C34 176.3(5) . . . . ?
N36 C32 N33 C37 178.6(5) . . . . ?
C31 C32 N33 C37 -4.7(9) . . . . ?
C32 N33 C34 C35 0.8(6) . . . . ?
C37 N33 C34 C35 -178.2(5) . . . . ?
N33 C34 C35 N36 -0.8(6) . . . . ?
N33 C32 N36 C35 0.0(6) . . . . ?
C31 C32 N36 C35 -177.2(5) . . . . ?
N33 C32 N36 Cu21 175.7(3) . . . . ?
C31 C32 N36 Cu21 -1.4(6) . . . . ?
C34 C35 N36 C32 0.5(6) . . . . ?
C34 C35 N36 Cu21 -173.3(4) . . . . ?
O53B Cl5B O55B Cu1 35(5) . . . . ?
O54B Cl5B O55B Cu1 -86(5) . . . . ?
O52B Cl5B O55B Cu1 156(5) . . . . ?
O64B Cl6B O65B Cu21 -32.6(17) . . . 1_565 ?
O63B Cl6B O65B Cu21 87.4(16) . . . 1_565 ?
O62B Cl6B O65B Cu21 -151.8(15) . . . 1_565 ?

_refine_diff_density_max         1.510
_refine_diff_density_min         -1.098
_refine_diff_density_rms         0.103



_exptl_crystal_recrystallization_method 
'diffusion of diethyl ether in a methanol solution of the compound'
####################################################################### 
# 
# 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_ms_ugd-04-061
_database_code_depnum_ccdc_archive 'CCDC 2369753'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2025-01-07 deposited with the CCDC.	2025-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H13 Cl Cu N5, Cl O4'
_chemical_formula_sum            'C9 H13 Cl2 Cu N5 O4'
_chemical_formula_weight         389.68

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   6.3467(8)
_cell_length_b                   17.642(2)
_cell_length_c                   13.4662(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1507.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2486
_cell_measurement_theta_min      3.3830
_cell_measurement_theta_max      26.1890

_exptl_crystal_description       block
_exptl_crystal_colour            'pale blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_F_000             788
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    1.824
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.85609
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?



_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'57 images, ΔΦ 2.5° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7905
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.411
_diffrn_reflns_theta_max         26.391
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             2959
_reflns_number_gt                2327
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_max     0.939
_reflns_Friedel_fraction_full    0.968

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       MAR
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     'dual space'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;


_refine_special_details          'Refined as a 2-component inversion twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0894P)²+0.8701P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.45(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2959
_refine_ls_number_parameters     191
_refine_ls_number_restraints     118
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1660
_refine_ls_wR_factor_gt          0.1541
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.39095(15) 0.70094(5) 0.63612(15) 0.0429(3) Uani 1 1 d . . . . .
Cl2 Cl 0.3786(4) 0.83111(12) 0.6355(6) 0.0638(6) Uani 1 1 d . . . . .
N3 N 0.3856(18) 0.6946(9) 0.7781(12) 0.051(4) Uani 1 1 d . U . . .
C4 C 0.395(3) 0.7481(13) 0.8528(15) 0.061(5) Uani 1 1 d . U . . .
H4 H 0.397428 0.800361 0.843694 0.074 Uiso 1 1 calc R U . . .
N5 N 0.401(2) 0.7109(11) 0.9437(10) 0.062(5) Uani 1 1 d . U . . .
H5 H 0.415144 0.732583 1.000481 0.075 Uiso 1 1 calc R U . . .
C6 C 0.380(3) 0.6373(13) 0.9295(14) 0.072(5) Uani 1 1 d . U . . .
H6 H 0.380297 0.599720 0.977932 0.087 Uiso 1 1 calc R U . . .
C7 C 0.360(4) 0.6277(15) 0.8322(15) 0.083(6) Uani 1 1 d . U . . .
C8 C 0.302(3) 0.5478(7) 0.7812(11) 0.075(3) Uani 1 1 d . U . . .
H8A H 0.327407 0.507276 0.828296 0.090 Uiso 1 1 calc R U . . .
H8B H 0.152731 0.547376 0.764855 0.090 Uiso 1 1 calc R U . . .
C9 C 0.421(2) 0.5341(7) 0.6931(11) 0.070(3) Uani 1 1 d . U . . .
H9A H 0.397439 0.482610 0.670654 0.084 Uiso 1 1 calc R U . . .
H9B H 0.570312 0.539637 0.707672 0.084 Uiso 1 1 calc R U . . .
N10 N 0.3633(16) 0.5863(5) 0.6154(9) 0.071(3) Uani 1 1 d . U . . .
H10 H 0.210766 0.578965 0.609724 0.085 Uiso 1 1 calc R U . . .
C11 C 0.443(3) 0.5643(9) 0.5139(12) 0.085(4) Uani 1 1 d . U . . .
H11A H 0.593857 0.556146 0.516095 0.102 Uiso 1 1 calc R U . . .
H11B H 0.376028 0.517586 0.492582 0.102 Uiso 1 1 calc R U . . .
C12 C 0.393(3) 0.6257(12) 0.4440(11) 0.076(6) Uani 1 1 d . U . . .
N13 N 0.3964(17) 0.6962(9) 0.4893(13) 0.050(4) Uani 1 1 d . U . . .
C14 C 0.402(2) 0.7474(12) 0.4223(13) 0.053(5) Uani 1 1 d . U . . .
H14 H 0.415275 0.798963 0.435109 0.064 Uiso 1 1 calc R U . . .
N15 N 0.388(2) 0.7188(12) 0.3364(12) 0.064(4) Uani 1 1 d . U . . .
H15 H 0.384475 0.744017 0.281706 0.077 Uiso 1 1 calc R U . . .
C16 C 0.381(4) 0.6423(17) 0.3441(16) 0.090(7) Uani 1 1 d . U . . .
H16 H 0.369210 0.607810 0.292162 0.109 Uiso 1 1 calc R U . . .
Cl21 Cl 0.4736(4) 0.86936(13) 0.1385(4) 0.0646(6) Uani 1 1 d . . . . .
O22 O 0.5904(17) 0.7993(5) 0.1354(17) 0.110(3) Uani 1 1 d . . . . .
O23 O 0.6003(18) 0.9334(6) 0.1448(18) 0.118(4) Uani 1 1 d . . . . .
O24 O 0.338(3) 0.8710(11) 0.2236(13) 0.124(6) Uani 1 1 d . . . . .
O25 O 0.355(2) 0.8675(11) 0.0482(8) 0.098(5) Uani 1 1 d . . . . .


_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 N3 1.916(17) . ?
Cu1 N13 1.980(18) . ?
Cu1 N10 2.049(10) . ?
Cu1 Cl2 2.298(2) . ?
N3 C4 1.38(3) . ?
N3 C7 1.40(3) . ?
C4 N5 1.39(2) . ?
C4 H4 0.9300 . ?
N5 C6 1.32(3) . ?
N5 H5 0.8600 . ?
C6 C7 1.33(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.61(3) . ?
C8 C9 1.430(19) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N10 1.441(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
N10 C11 1.51(2) . ?
N10 H10 0.9800 . ?
C11 C12 1.47(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C16 1.38(3) . ?
C12 N13 1.38(3) . ?
N13 C14 1.28(3) . ?
C14 N15 1.27(2) . ?
C14 H14 0.9300 . ?
N15 C16 1.35(4) . ?
N15 H15 0.8600 . ?
C16 H16 0.9300 . ?
Cl21 O23 1.390(10) . ?
Cl21 O25 1.429(12) . ?
Cl21 O24 1.434(14) . ?
Cl21 O22 1.441(9) . ?

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 174.2(3) . . ?
N3 Cu1 N10 94.4(6) . . ?
N13 Cu1 N10 79.8(6) . . ?
N3 Cu1 Cl2 93.5(5) . . ?
N13 Cu1 Cl2 92.3(5) . . ?
N10 Cu1 Cl2 169.4(4) . . ?
C4 N3 C7 101.7(17) . . ?
C4 N3 Cu1 133.3(15) . . ?
C7 N3 Cu1 124.9(15) . . ?
N3 C4 N5 108.7(18) . . ?
N3 C4 H4 125.7 . . ?
N5 C4 H4 125.7 . . ?
C6 N5 C4 109.6(15) . . ?
C6 N5 H5 125.2 . . ?
C4 N5 H5 125.2 . . ?
N5 C6 C7 106.1(19) . . ?
N5 C6 H6 126.9 . . ?
C7 C6 H6 126.9 . . ?
C6 C7 N3 113(2) . . ?
C6 C7 C8 124(2) . . ?
N3 C7 C8 123.0(17) . . ?
C9 C8 C7 112.3(14) . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 N10 111.0(11) . . ?
C8 C9 H9A 109.4 . . ?
N10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
N10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C9 N10 C11 114.1(10) . . ?
C9 N10 Cu1 120.7(9) . . ?
C11 N10 Cu1 110.4(9) . . ?
C9 N10 H10 103.0 . . ?
C11 N10 H10 103.0 . . ?
Cu1 N10 H10 103.0 . . ?
C12 C11 N10 108.6(12) . . ?
C12 C11 H11A 110.0 . . ?
N10 C11 H11A 110.0 . . ?
C12 C11 H11B 110.0 . . ?
N10 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
C16 C12 N13 104(2) . . ?
C16 C12 C11 142.5(18) . . ?
N13 C12 C11 112.1(14) . . ?
C14 N13 C12 108.9(17) . . ?
C14 N13 Cu1 132.5(15) . . ?
C12 N13 Cu1 118.6(14) . . ?
N15 C14 N13 111(2) . . ?
N15 C14 H14 124.4 . . ?
N13 C14 H14 124.4 . . ?
C14 N15 C16 109.2(16) . . ?
C14 N15 H15 125.4 . . ?
C16 N15 H15 125.4 . . ?
N15 C16 C12 107(2) . . ?
N15 C16 H16 126.7 . . ?
C12 C16 H16 126.7 . . ?
O23 Cl21 O25 112.1(13) . . ?
O23 Cl21 O24 106.4(13) . . ?
O25 Cl21 O24 111.4(7) . . ?
O23 Cl21 O22 113.6(7) . . ?
O25 Cl21 O22 103.1(11) . . ?
O24 Cl21 O22 110.4(12) . . ?

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 7(2) . . . . ?
Cu1 N3 C4 N5 -175.6(9) . . . . ?
N3 C4 N5 C6 -4(2) . . . . ?
C4 N5 C6 C7 -1(2) . . . . ?
N5 C6 C7 N3 6(2) . . . . ?
N5 C6 C7 C8 -172.0(19) . . . . ?
C4 N3 C7 C6 -8(2) . . . . ?
Cu1 N3 C7 C6 174.4(12) . . . . ?
C4 N3 C7 C8 169.6(17) . . . . ?
Cu1 N3 C7 C8 -8(3) . . . . ?
C6 C7 C8 C9 -139(2) . . . . ?
N3 C7 C8 C9 44(2) . . . . ?
C7 C8 C9 N10 -67.8(16) . . . . ?
C8 C9 N10 C11 -166.1(12) . . . . ?
C8 C9 N10 Cu1 58.7(13) . . . . ?
C9 N10 C11 C12 -174.0(14) . . . . ?
Cu1 N10 C11 C12 -34.4(16) . . . . ?
N10 C11 C12 C16 -165(3) . . . . ?
N10 C11 C12 N13 32(2) . . . . ?
C16 C12 N13 C14 -5(2) . . . . ?
C11 C12 N13 C14 164.7(15) . . . . ?
C16 C12 N13 Cu1 175.3(13) . . . . ?
C11 C12 N13 Cu1 -16(2) . . . . ?
C12 N13 C14 N15 5(2) . . . . ?
Cu1 N13 C14 N15 -175.2(10) . . . . ?
N13 C14 N15 C16 -3(2) . . . . ?
C14 N15 C16 C12 0(2) . . . . ?
N13 C12 C16 N15 3(2) . . . . ?
C11 C12 C16 N15 -160(3) . . . . ?

_refine_diff_density_max         0.559
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.099



_exptl_crystal_recrystallization_method 
'diffusion of diethyl ether in a methanol solution of the compound'
####################################################################### 
# 
# 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_ms_ug84
_database_code_depnum_ccdc_archive 'CCDC 2369754'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2024-07-10 deposited with the CCDC.	2025-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_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

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.5005(15)
_cell_length_b                   8.931(2)
_cell_length_c                   12.916(2)
_cell_angle_alpha                80.624(17)
_cell_angle_beta                 73.129(16)
_cell_angle_gamma                69.64(2)
_cell_volume                     774.4(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2625
_cell_measurement_theta_min      2.8300
_cell_measurement_theta_max      26.0990

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_F_000             410
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.779
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.85032
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'60 images, ΔΦ 3.0° '
'60 images, ΔΦ 3.0° (2nd orientation)'
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10998
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.849
_diffrn_reflns_theta_max         26.203
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3043
_reflns_number_gt                2696
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       MAR
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     'dual space'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0601P)²+0.7141P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3043
_refine_ls_number_parameters     246
_refine_ls_number_restraints     56
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1130
_refine_ls_wR_factor_gt          0.1098
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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


_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 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_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_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) . . . . ?

_refine_diff_density_max         0.504
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.069



_exptl_crystal_recrystallization_method 
'diffusion of diethyl ether in a methanol solution of the compound'
####################################################################### 
# 
# 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_ms_ugd_02-101
_database_code_depnum_ccdc_archive 'CCDC 2369756'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2024-07-10 deposited with the CCDC.	2025-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H14 Cl Cu N4, O4 Cl'
_chemical_formula_sum            'C11 H14 Cl2 Cu N4 O4'
_chemical_formula_weight         400.70

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.8007(9)
_cell_length_b                   8.0922(4)
_cell_length_c                   15.2526(10)
_cell_angle_alpha                90
_cell_angle_beta                 108.525(7)
_cell_angle_gamma                90
_cell_volume                     1498.09(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    6425
_cell_measurement_theta_min      3.0050
_cell_measurement_theta_max      26.2990

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_F_000             812
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.837
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.45546
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?




_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'90 images, ΔΦ 2.5° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12848
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.104
_diffrn_reflns_theta_max         26.323
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3021
_reflns_number_gt                2760
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       MAR
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     dual
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0357P)²+1.0850P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3021
_refine_ls_number_parameters     372
_refine_ls_number_restraints     363
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0767
_refine_ls_wR_factor_gt          0.0747
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.39051(2) 0.69222(4) 0.25447(2) 0.03887(11) Uani 1 1 d . U . . .
Cl2 Cl 0.23768(6) 0.56892(11) 0.26603(5) 0.0705(2) Uani 1 1 d . . . . .
N11 N 0.4526(7) 0.7320(11) 0.3852(3) 0.0419(15) Uani 0.822(11) 1 d D U P A 1
C12 C 0.4344(7) 0.6838(12) 0.4615(3) 0.0471(15) Uani 0.822(11) 1 d D U P A 1
H12 H 0.375556 0.618748 0.464102 0.057 Uiso 0.822(11) 1 calc R U P A 1
N13 N 0.5134(6) 0.7427(10) 0.5344(3) 0.0509(13) Uani 0.822(11) 1 d D U P A 1
H13 H 0.517704 0.727588 0.591256 0.061 Uiso 0.822(11) 1 calc R U P A 1
C14 C 0.5863(5) 0.8306(8) 0.5046(3) 0.0493(14) Uani 0.822(11) 1 d D U P A 1
H14 H 0.648886 0.885501 0.541050 0.059 Uiso 0.822(11) 1 calc R U P A 1
C15 C 0.5494(6) 0.8220(8) 0.4112(3) 0.0383(13) Uani 0.822(11) 1 d D U P A 1
C16 C 0.5873(3) 0.8864(6) 0.3345(2) 0.0389(9) Uani 0.822(11) 1 d D U P A 1
H16A H 0.616203 0.997531 0.348391 0.047 Uiso 0.822(11) 1 calc R U P A 1
H16B H 0.644800 0.816213 0.326053 0.047 Uiso 0.822(11) 1 calc R U P A 1
N17 N 0.4896(2) 0.8861(5) 0.2498(2) 0.0330(8) Uani 0.822(11) 1 d D U P A 1
H17 H 0.447537 0.984535 0.255384 0.040 Uiso 0.822(11) 1 calc R U P A 1
C18 C 0.5181(5) 0.9119(8) 0.1642(3) 0.0414(13) Uani 0.822(11) 1 d D U P A 1
H18A H 0.572996 0.831772 0.160765 0.050 Uiso 0.822(11) 1 calc R U P A 1
H18B H 0.548534 1.021647 0.164280 0.050 Uiso 0.822(11) 1 calc R U P A 1
C19 C 0.4142(5) 0.8922(6) 0.0810(3) 0.0433(12) Uani 0.822(11) 1 d D U P A 1
H19A H 0.353659 0.948565 0.093639 0.052 Uiso 0.822(11) 1 calc R U P A 1
H19B H 0.425867 0.944926 0.027735 0.052 Uiso 0.822(11) 1 calc R U P A 1
C20 C 0.3830(6) 0.7155(7) 0.0580(3) 0.0356(11) Uani 0.822(11) 1 d D U P A 1
N21 N 0.3738(5) 0.6166(6) 0.1266(3) 0.0331(10) Uani 0.822(11) 1 d D U P A 1
C22 C 0.3518(6) 0.4558(7) 0.1083(4) 0.0437(13) Uani 0.822(11) 1 d D U P A 1
H22 H 0.344287 0.387783 0.155102 0.052 Uiso 0.822(11) 1 calc R U P A 1
C23 C 0.3400(6) 0.3877(7) 0.0230(4) 0.0505(15) Uani 0.822(11) 1 d D U P A 1
H23 H 0.326314 0.275321 0.012806 0.061 Uiso 0.822(11) 1 calc R U P A 1
C24 C 0.3487(6) 0.4872(8) -0.0463(3) 0.0509(14) Uani 0.822(11) 1 d D U P A 1
H24 H 0.339490 0.443972 -0.104731 0.061 Uiso 0.822(11) 1 calc R U P A 1
C25 C 0.3711(7) 0.6515(8) -0.0291(3) 0.0445(11) Uani 0.822(11) 1 d D U P A 1
H25 H 0.378304 0.720180 -0.075676 0.053 Uiso 0.822(11) 1 calc R U P A 1
N11B N 0.469(3) 0.733(4) 0.3883(10) 0.031(5) Uani 0.178(11) 1 d D U P A 2
C12B C 0.455(2) 0.694(4) 0.4683(12) 0.030(5) Uani 0.178(11) 1 d D U P A 2
H12B H 0.400163 0.626663 0.476108 0.036 Uiso 0.178(11) 1 calc R U P A 2
N13B N 0.534(2) 0.768(4) 0.5360(11) 0.033(4) Uani 0.178(11) 1 d D U P A 2
H13B H 0.546337 0.752336 0.594181 0.040 Uiso 0.178(11) 1 calc R U P A 2
C14B C 0.5916(19) 0.872(3) 0.4989(10) 0.028(4) Uani 0.178(11) 1 d D U P A 2
H14B H 0.649953 0.940442 0.530571 0.033 Uiso 0.178(11) 1 calc R U P A 2
C15B C 0.547(2) 0.857(4) 0.4061(9) 0.029(5) Uani 0.178(11) 1 d D U P A 2
C16B C 0.5662(18) 0.937(2) 0.3249(10) 0.040(4) Uani 0.178(11) 1 d D U P A 2
H16C H 0.536284 1.048114 0.317013 0.048 Uiso 0.178(11) 1 calc R U P A 2
H16D H 0.644629 0.943571 0.334194 0.048 Uiso 0.178(11) 1 calc R U P A 2
N17B N 0.5115(15) 0.836(2) 0.2425(8) 0.036(4) Uani 0.178(11) 1 d D U P A 2
H17B H 0.568718 0.755177 0.243725 0.044 Uiso 0.178(11) 1 calc R U P A 2
C18B C 0.498(2) 0.922(3) 0.1541(10) 0.035(5) Uani 0.178(11) 1 d D U P A 2
H18C H 0.560330 0.898546 0.133339 0.043 Uiso 0.178(11) 1 calc R U P A 2
H18D H 0.495484 1.040788 0.163354 0.043 Uiso 0.178(11) 1 calc R U P A 2
C19B C 0.3921(18) 0.8677(19) 0.0805(12) 0.031(4) Uani 0.178(11) 1 d D U P A 2
H19C H 0.329588 0.907460 0.097391 0.037 Uiso 0.178(11) 1 calc R U P A 2
H19D H 0.388830 0.918683 0.022148 0.037 Uiso 0.178(11) 1 calc R U P A 2
C20B C 0.382(3) 0.685(2) 0.0676(13) 0.025(4) Uani 0.178(11) 1 d D U P A 2
N21B N 0.356(2) 0.596(2) 0.1325(11) 0.023(4) Uani 0.178(11) 1 d D U P A 2
C22B C 0.341(3) 0.433(2) 0.1218(13) 0.022(4) Uani 0.178(11) 1 d D U P A 2
H22B H 0.337365 0.369656 0.171601 0.026 Uiso 0.178(11) 1 calc R U P A 2
C23B C 0.330(3) 0.357(2) 0.0385(14) 0.026(4) Uani 0.178(11) 1 d D U P A 2
H23B H 0.313105 0.245280 0.030476 0.031 Uiso 0.178(11) 1 calc R U P A 2
C24B C 0.343(3) 0.449(2) -0.0316(14) 0.029(4) Uani 0.178(11) 1 d D U P A 2
H24B H 0.335641 0.399599 -0.088416 0.034 Uiso 0.178(11) 1 calc R U P A 2
C25B C 0.368(3) 0.613(2) -0.0186(13) 0.030(4) Uani 0.178(11) 1 d D U P A 2
H25B H 0.376232 0.676374 -0.066951 0.036 Uiso 0.178(11) 1 calc R U P A 2
Cl31 Cl 0.36376(5) 0.60120(8) 0.69467(4) 0.04982(17) Uani 1 1 d . U . . .
O32 O 0.4039(7) 0.4675(9) 0.7503(5) 0.071(2) Uani 0.57(2) 1 d D U P B 1
O33 O 0.2983(7) 0.7049(13) 0.7341(7) 0.094(3) Uani 0.57(2) 1 d D U P B 1
O34 O 0.4637(6) 0.7060(12) 0.7012(5) 0.0729(19) Uani 0.57(2) 1 d D U P B 1
O35 O 0.3129(9) 0.5711(19) 0.6044(5) 0.102(3) Uani 0.57(2) 1 d D U P B 1
O32B O 0.3528(18) 0.4552(13) 0.7481(9) 0.100(4) Uani 0.43(2) 1 d D U P B 2
O33B O 0.3238(15) 0.7295(15) 0.7273(12) 0.127(5) Uani 0.43(2) 1 d D U P B 2
O34B O 0.4704(6) 0.605(3) 0.6946(7) 0.096(5) Uani 0.43(2) 1 d D U P B 2
O35B O 0.2917(15) 0.554(2) 0.6008(9) 0.110(5) Uani 0.43(2) 1 d D U P B 2


_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 N11 1.924(4) . ?
Cu1 N21B 1.932(13) . ?
Cu1 N21 1.990(3) . ?
Cu1 N17B 1.992(14) . ?
Cu1 N11B 1.995(15) . ?
Cu1 N17 2.033(3) . ?
Cu1 Cl2 2.2524(7) . ?
N11 C12 1.317(4) . ?
N11 C15 1.382(5) . ?
C12 N13 1.331(5) . ?
C12 H12 0.9300 . ?
N13 C14 1.362(5) . ?
N13 H13 0.8600 . ?
C14 C15 1.352(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.495(5) . ?
C16 N17 1.485(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
N17 C18 1.478(4) . ?
N17 H17 0.9800 . ?
C18 C19 1.527(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.496(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 N21 1.352(4) . ?
C20 C25 1.388(4) . ?
N21 C22 1.341(4) . ?
C22 C23 1.377(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.360(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.367(6) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
N11B C12B 1.321(9) . ?
N11B C15B 1.380(9) . ?
C12B N13B 1.334(10) . ?
C12B H12B 0.9300 . ?
N13B C14B 1.357(10) . ?
N13B H13B 0.8600 . ?
C14B C15B 1.354(9) . ?
C14B H14B 0.9300 . ?
C15B C16B 1.488(9) . ?
C16B N17B 1.475(9) . ?
C16B H16C 0.9700 . ?
C16B H16D 0.9700 . ?
N17B C18B 1.478(10) . ?
N17B H17B 0.9800 . ?
C18B C19B 1.523(10) . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
C19B C20B 1.495(10) . ?
C19B H19C 0.9700 . ?
C19B H19D 0.9700 . ?
C20B N21B 1.349(9) . ?
C20B C25B 1.396(9) . ?
N21B C22B 1.337(9) . ?
C22B C23B 1.377(9) . ?
C22B H22B 0.9300 . ?
C23B C24B 1.356(10) . ?
C23B H23B 0.9300 . ?
C24B C25B 1.366(10) . ?
C24B H24B 0.9300 . ?
C25B H25B 0.9300 . ?
Cl31 O33B 1.323(11) . ?
Cl31 O35 1.345(7) . ?
Cl31 O34B 1.366(7) . ?
Cl31 O32 1.370(6) . ?
Cl31 O33 1.445(7) . ?
Cl31 O32B 1.467(8) . ?
Cl31 O35B 1.487(13) . ?
Cl31 O34 1.512(5) . ?

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
N11 Cu1 N21 161.3(3) . . ?
N21B Cu1 N17B 95.4(6) . . ?
N21B Cu1 N11B 159.8(15) . . ?
N17B Cu1 N11B 81.2(5) . . ?
N11 Cu1 N17 81.37(15) . . ?
N21 Cu1 N17 94.43(14) . . ?
N11 Cu1 Cl2 94.37(15) . . ?
N21B Cu1 Cl2 87.6(6) . . ?
N21 Cu1 Cl2 96.60(16) . . ?
N17B Cu1 Cl2 170.4(6) . . ?
N11B Cu1 Cl2 99.1(6) . . ?
N17 Cu1 Cl2 155.74(13) . . ?
C12 N11 C15 107.2(3) . . ?
C12 N11 Cu1 137.4(3) . . ?
C15 N11 Cu1 115.0(3) . . ?
N11 C12 N13 109.4(4) . . ?
N11 C12 H12 125.3 . . ?
N13 C12 H12 125.3 . . ?
C12 N13 C14 109.1(3) . . ?
C12 N13 H13 125.4 . . ?
C14 N13 H13 125.4 . . ?
C15 C14 N13 106.1(3) . . ?
C15 C14 H14 126.9 . . ?
N13 C14 H14 126.9 . . ?
C14 C15 N11 108.1(3) . . ?
C14 C15 C16 135.6(4) . . ?
N11 C15 C16 116.3(3) . . ?
N17 C16 C15 106.7(3) . . ?
N17 C16 H16A 110.4 . . ?
C15 C16 H16A 110.4 . . ?
N17 C16 H16B 110.4 . . ?
C15 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
C18 N17 C16 113.1(3) . . ?
C18 N17 Cu1 118.1(3) . . ?
C16 N17 Cu1 109.5(3) . . ?
C18 N17 H17 105.0 . . ?
C16 N17 H17 105.0 . . ?
Cu1 N17 H17 105.0 . . ?
N17 C18 C19 109.0(4) . . ?
N17 C18 H18A 109.9 . . ?
C19 C18 H18A 109.9 . . ?
N17 C18 H18B 109.9 . . ?
C19 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
C20 C19 C18 113.1(3) . . ?
C20 C19 H19A 109.0 . . ?
C18 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
C18 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
N21 C20 C25 120.6(4) . . ?
N21 C20 C19 117.8(3) . . ?
C25 C20 C19 121.4(4) . . ?
C22 N21 C20 118.5(3) . . ?
C22 N21 Cu1 116.9(3) . . ?
C20 N21 Cu1 124.6(3) . . ?
N21 C22 C23 122.5(4) . . ?
N21 C22 H22 118.8 . . ?
C23 C22 H22 118.8 . . ?
C24 C23 C22 119.0(4) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C23 C24 C25 119.4(3) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C24 C25 C20 119.9(4) . . ?
C24 C25 H25 120.0 . . ?
C20 C25 H25 120.0 . . ?
C12B N11B C15B 106.7(9) . . ?
C12B N11B Cu1 137.5(12) . . ?
C15B N11B Cu1 114.6(9) . . ?
N11B C12B N13B 108.8(10) . . ?
N11B C12B H12B 125.6 . . ?
N13B C12B H12B 125.6 . . ?
C12B N13B C14B 109.4(9) . . ?
C12B N13B H13B 125.3 . . ?
C14B N13B H13B 125.3 . . ?
C15B C14B N13B 105.7(9) . . ?
C15B C14B H14B 127.1 . . ?
N13B C14B H14B 127.1 . . ?
C14B C15B N11B 108.3(9) . . ?
C14B C15B C16B 134.4(11) . . ?
N11B C15B C16B 117.2(9) . . ?
N17B C16B C15B 108.0(9) . . ?
N17B C16B H16C 110.1 . . ?
C15B C16B H16C 110.1 . . ?
N17B C16B H16D 110.1 . . ?
C15B C16B H16D 110.1 . . ?
H16C C16B H16D 108.4 . . ?
C16B N17B C18B 113.8(11) . . ?
C16B N17B Cu1 114.7(10) . . ?
C18B N17B Cu1 119.3(11) . . ?
C16B N17B H17B 101.8 . . ?
C18B N17B H17B 101.8 . . ?
Cu1 N17B H17B 101.8 . . ?
N17B C18B C19B 110.8(12) . . ?
N17B C18B H18C 109.5 . . ?
C19B C18B H18C 109.5 . . ?
N17B C18B H18D 109.5 . . ?
C19B C18B H18D 109.5 . . ?
H18C C18B H18D 108.1 . . ?
C20B C19B C18B 113.7(13) . . ?
C20B C19B H19C 108.8 . . ?
C18B C19B H19C 108.8 . . ?
C20B C19B H19D 108.8 . . ?
C18B C19B H19D 108.8 . . ?
H19C C19B H19D 107.7 . . ?
N21B C20B C25B 119.0(10) . . ?
N21B C20B C19B 117.2(12) . . ?
C25B C20B C19B 121.1(12) . . ?
C22B N21B C20B 119.5(11) . . ?
C22B N21B Cu1 119.6(12) . . ?
C20B N21B Cu1 117.4(9) . . ?
N21B C22B C23B 121.5(11) . . ?
N21B C22B H22B 119.3 . . ?
C23B C22B H22B 119.3 . . ?
C24B C23B C22B 118.8(11) . . ?
C24B C23B H23B 120.6 . . ?
C22B C23B H23B 120.6 . . ?
C23B C24B C25B 120.0(11) . . ?
C23B C24B H24B 120.0 . . ?
C25B C24B H24B 120.0 . . ?
C24B C25B C20B 119.6(11) . . ?
C24B C25B H25B 120.2 . . ?
C20B C25B H25B 120.2 . . ?
O33B Cl31 O34B 119.3(9) . . ?
O35 Cl31 O32 117.1(7) . . ?
O35 Cl31 O33 112.0(6) . . ?
O32 Cl31 O33 110.7(5) . . ?
O33B Cl31 O32B 107.8(7) . . ?
O34B Cl31 O32B 106.9(5) . . ?
O33B Cl31 O35B 111.7(8) . . ?
O34B Cl31 O35B 108.6(8) . . ?
O32B Cl31 O35B 100.8(9) . . ?
O35 Cl31 O34 107.1(5) . . ?
O32 Cl31 O34 105.0(3) . . ?
O33 Cl31 O34 103.7(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
C15 N11 C12 N13 1.7(12) . . . . ?
Cu1 N11 C12 N13 173.9(10) . . . . ?
N11 C12 N13 C14 -0.8(12) . . . . ?
C12 N13 C14 C15 -0.5(10) . . . . ?
N13 C14 C15 N11 1.5(9) . . . . ?
N13 C14 C15 C16 -179.4(8) . . . . ?
C12 N11 C15 C14 -1.9(11) . . . . ?
Cu1 N11 C15 C14 -176.2(6) . . . . ?
C12 N11 C15 C16 178.8(8) . . . . ?
Cu1 N11 C15 C16 4.5(10) . . . . ?
C14 C15 C16 N17 -159.2(8) . . . . ?
N11 C15 C16 N17 19.8(8) . . . . ?
C15 C16 N17 C18 -167.5(5) . . . . ?
C15 C16 N17 Cu1 -33.5(5) . . . . ?
C16 N17 C18 C19 174.3(4) . . . . ?
Cu1 N17 C18 C19 44.6(7) . . . . ?
N17 C18 C19 C20 -78.2(6) . . . . ?
C18 C19 C20 N21 52.3(7) . . . . ?
C18 C19 C20 C25 -123.4(7) . . . . ?
C25 C20 N21 C22 -0.7(11) . . . . ?
C19 C20 N21 C22 -176.4(6) . . . . ?
C25 C20 N21 Cu1 179.4(6) . . . . ?
C19 C20 N21 Cu1 3.7(9) . . . . ?
C20 N21 C22 C23 1.0(11) . . . . ?
Cu1 N21 C22 C23 -179.0(6) . . . . ?
N21 C22 C23 C24 -1.4(12) . . . . ?
C22 C23 C24 C25 1.3(12) . . . . ?
C23 C24 C25 C20 -1.0(12) . . . . ?
N21 C20 C25 C24 0.7(12) . . . . ?
C19 C20 C25 C24 176.2(7) . . . . ?
C15B N11B C12B N13B -10(5) . . . . ?
Cu1 N11B C12B N13B -176(4) . . . . ?
N11B C12B N13B C14B 7(5) . . . . ?
C12B N13B C14B C15B -1(4) . . . . ?
N13B C14B C15B N11B -5(4) . . . . ?
N13B C14B C15B C16B 178(4) . . . . ?
C12B N11B C15B C14B 10(5) . . . . ?
Cu1 N11B C15B C14B 179(3) . . . . ?
C12B N11B C15B C16B -173(3) . . . . ?
Cu1 N11B C15B C16B -3(5) . . . . ?
C14B C15B C16B N17B 165(4) . . . . ?
N11B C15B C16B N17B -12(4) . . . . ?
C15B C16B N17B C18B 164(2) . . . . ?
C15B C16B N17B Cu1 22(3) . . . . ?
C16B N17B C18B C19B -147(2) . . . . ?
Cu1 N17B C18B C19B -6(3) . . . . ?
N17B C18B C19B C20B -53(2) . . . . ?
C18B C19B C20B N21B 76(3) . . . . ?
C18B C19B C20B C25B -123(3) . . . . ?
C25B C20B N21B C22B 15(5) . . . . ?
C19B C20B N21B C22B 177(2) . . . . ?
C25B C20B N21B Cu1 174(3) . . . . ?
C19B C20B N21B Cu1 -24(3) . . . . ?
C20B N21B C22B C23B -13(4) . . . . ?
Cu1 N21B C22B C23B -172(2) . . . . ?
N21B C22B C23B C24B 5(5) . . . . ?
C22B C23B C24B C25B 1(5) . . . . ?
C23B C24B C25B C20B 2(6) . . . . ?
N21B C20B C25B C24B -9(5) . . . . ?
C19B C20B C25B C24B -170(3) . . . . ?

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.055



_exptl_crystal_recrystallization_method 
'diffusion of diethyl ether in a methanol solution of the compound'
####################################################################### 
# 
# 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_ms_ugd_02-017
_database_code_depnum_ccdc_archive 'CCDC 2369758'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2024-07-10 deposited with the CCDC.	2025-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C56 H54 Cl2 Cu2 N10, 2(F6 P)'
_chemical_formula_sum            'C56 H54 Cl2 Cu2 F12 N10 P2'
_chemical_formula_weight         1355.01

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   33.2550(11)
_cell_length_b                   7.3015(3)
_cell_length_c                   23.7923(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.704(3)
_cell_angle_gamma                90
_cell_volume                     5694.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    7804
_cell_measurement_theta_min      3.0000
_cell_measurement_theta_max      26.3020

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_F_000             2760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.985
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.90673
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?



_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'150 images, ΔΦ 1.2° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19900
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.018
_diffrn_reflns_theta_max         26.332
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5755
_reflns_number_gt                4672
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       MAR
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     dual
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0529P)²+10.5038P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5755
_refine_ls_number_parameters     404
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1129
_refine_ls_wR_factor_gt          0.1061
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.46502(2) 0.55618(4) 0.54495(2) 0.03069(11) Uani 1 1 d . . . . .
Cl2 Cl 0.48622(2) 0.26768(9) 0.52005(3) 0.03881(17) Uani 1 1 d . . . . .
N3 N 0.50278(7) 0.5658(3) 0.61697(10) 0.0365(5) Uani 1 1 d . . . . .
C4 C 0.52017(10) 0.4263(5) 0.64654(14) 0.0506(8) Uani 1 1 d . . . . .
H4 H 0.519206 0.305641 0.633837 0.061 Uiso 1 1 calc R U . . .
N5 N 0.53937(9) 0.4826(4) 0.69733(12) 0.0615(8) Uani 1 1 d . . . . .
H5 H 0.552722 0.414084 0.723398 0.074 Uiso 1 1 calc R U . . .
C6 C 0.53431(10) 0.6654(5) 0.70093(14) 0.0528(8) Uani 1 1 d . . . . .
H6 H 0.544413 0.740274 0.731710 0.063 Uiso 1 1 calc R U . . .
C7 C 0.51161(9) 0.7184(4) 0.65089(13) 0.0409(7) Uani 1 1 d . . . . .
C8 C 0.49716(10) 0.9048(4) 0.63125(15) 0.0506(8) Uani 1 1 d . . . . .
H8A H 0.510902 0.941797 0.600209 0.061 Uiso 1 1 calc R U . A 1
H8B H 0.504711 0.990880 0.662293 0.061 Uiso 1 1 calc R U . A 1
C9 C 0.4520(6) 0.9148(15) 0.6115(7) 0.0417(9) Uani 0.809(10) 1 d D . P B 1
H9A H 0.438024 0.860510 0.640072 0.050 Uiso 0.809(10) 1 calc R U P B 1
H9B H 0.443674 1.041876 0.606763 0.050 Uiso 0.809(10) 1 calc R U P B 1
N10 N 0.44060(10) 0.8163(6) 0.55679(17) 0.0308(9) Uani 0.809(10) 1 d D . P B 1
H10 H 0.450622 0.894587 0.528667 0.037 Uiso 0.809(10) 1 calc R U P B 1
C11 C 0.39565(11) 0.8129(6) 0.5385(2) 0.0344(10) Uani 0.809(10) 1 d D . P B 1
H11A H 0.386139 0.931727 0.523594 0.041 Uiso 0.809(10) 1 calc R U P B 1
H11B H 0.382370 0.784825 0.570799 0.041 Uiso 0.809(10) 1 calc R U P B 1
C12 C 0.38553(13) 0.6700(7) 0.49352(19) 0.0256(11) Uani 0.809(10) 1 d D . P B 1
N13 N 0.41561(18) 0.5465(13) 0.4875(4) 0.0291(13) Uani 0.809(10) 1 d D . P B 1
C14 C 0.3995(2) 0.4258(13) 0.4490(4) 0.0300(14) Uani 0.809(10) 1 d D . P B 1
H14 H 0.413276 0.325756 0.437251 0.036 Uiso 0.809(10) 1 calc R U P B 1
N15 N 0.36047(18) 0.4675(14) 0.4290(4) 0.0267(12) Uani 0.809(10) 1 d D . P B 1
C16 C 0.35139(19) 0.625(2) 0.4564(8) 0.0343(13) Uani 0.809(10) 1 d D . P B 1
H16 H 0.326742 0.688474 0.450580 0.041 Uiso 0.809(10) 1 calc R U P B 1
C9B C 0.452(3) 0.914(6) 0.609(3) 0.0417(9) Uani 0.191(10) 1 d D . P B 2
H9C H 0.437855 0.921697 0.641388 0.050 Uiso 0.191(10) 1 calc R U P B 2
H9D H 0.446486 1.027065 0.587649 0.050 Uiso 0.191(10) 1 calc R U P B 2
N10B N 0.4325(5) 0.764(2) 0.5719(6) 0.0308(9) Uani 0.191(10) 1 d D . P B 2
H10B H 0.415086 0.702190 0.595496 0.037 Uiso 0.191(10) 1 calc R U P B 2
C11B C 0.4030(7) 0.836(2) 0.5230(7) 0.0344(10) Uani 0.191(10) 1 d D . P B 2
H11C H 0.415592 0.932097 0.503746 0.041 Uiso 0.191(10) 1 calc R U P B 2
H11D H 0.379244 0.886217 0.536149 0.041 Uiso 0.191(10) 1 calc R U P B 2
C12B C 0.3911(7) 0.679(3) 0.4835(9) 0.0256(11) Uani 0.191(10) 1 d D . P B 2
N13B N 0.4205(9) 0.547(6) 0.4826(19) 0.0291(13) Uani 0.191(10) 1 d D . P B 2
C14B C 0.4049(10) 0.426(6) 0.444(2) 0.0300(14) Uani 0.191(10) 1 d D . P B 2
H14B H 0.419176 0.326960 0.431969 0.036 Uiso 0.191(10) 1 calc R U P B 2
N15B N 0.3658(10) 0.465(6) 0.424(2) 0.0267(12) Uani 0.191(10) 1 d D . P B 2
C16B C 0.3557(9) 0.617(9) 0.453(4) 0.0343(13) Uani 0.191(10) 1 d D . P B 2
H16B H 0.329810 0.666755 0.451662 0.041 Uiso 0.191(10) 1 calc R U P B 2
C17 C 0.33026(7) 0.3479(4) 0.39157(11) 0.0298(6) Uani 1 1 d . . . . .
C18 C 0.35315(8) 0.2182(4) 0.35632(12) 0.0337(6) Uani 1 1 d . . . . .
C19 C 0.35299(9) 0.2380(5) 0.29841(13) 0.0427(7) Uani 1 1 d . . . . .
H19 H 0.339033 0.335163 0.278701 0.051 Uiso 1 1 calc R U . . .
C20 C 0.37355(10) 0.1137(6) 0.26985(15) 0.0581(9) Uani 1 1 d . . . . .
H20 H 0.372804 0.126875 0.230807 0.070 Uiso 1 1 calc R U . . .
C21 C 0.39499(11) -0.0285(5) 0.29796(18) 0.0608(10) Uani 1 1 d . . . . .
H21 H 0.409263 -0.109270 0.278370 0.073 Uiso 1 1 calc R U . . .
C22 C 0.39525(10) -0.0510(4) 0.35519(17) 0.0525(9) Uani 1 1 d . . . . .
H22 H 0.409710 -0.147321 0.374650 0.063 Uiso 1 1 calc R U . . .
C23 C 0.37401(9) 0.0696(4) 0.38383(14) 0.0416(7) Uani 1 1 d . . . . .
H23 H 0.373628 0.051202 0.422416 0.050 Uiso 1 1 calc R U . . .
C24 C 0.30104(8) 0.4827(4) 0.35491(11) 0.0323(6) Uani 1 1 d . . . . .
C25 C 0.25942(9) 0.4822(4) 0.35397(12) 0.0395(7) Uani 1 1 d . . . . .
H25 H 0.247833 0.395615 0.375033 0.047 Uiso 1 1 calc R U . . .
C26 C 0.23474(10) 0.6110(5) 0.32159(15) 0.0540(9) Uani 1 1 d . . . . .
H26 H 0.206747 0.610388 0.321391 0.065 Uiso 1 1 calc R U . . .
C27 C 0.25135(11) 0.7386(5) 0.29003(15) 0.0565(9) Uani 1 1 d . . . . .
H27 H 0.234664 0.823245 0.268101 0.068 Uiso 1 1 calc R U . . .
C28 C 0.29271(11) 0.7409(5) 0.29089(15) 0.0551(9) Uani 1 1 d . . . . .
H28 H 0.304146 0.827329 0.269571 0.066 Uiso 1 1 calc R U . . .
C29 C 0.31726(9) 0.6149(4) 0.32345(13) 0.0429(7) Uani 1 1 d . . . . .
H29 H 0.345308 0.618742 0.324310 0.052 Uiso 1 1 calc R U . . .
C30 C 0.30887(8) 0.2286(4) 0.43074(12) 0.0324(6) Uani 1 1 d . . . . .
C31 C 0.28109(9) 0.0974(4) 0.40582(14) 0.0427(7) Uani 1 1 d . . . . .
H31 H 0.275338 0.086840 0.366330 0.051 Uiso 1 1 calc R U . . .
C32 C 0.26206(10) -0.0168(4) 0.43916(16) 0.0514(8) Uani 1 1 d . . . . .
H32 H 0.242908 -0.101230 0.421972 0.062 Uiso 1 1 calc R U . . .
C33 C 0.27110(11) -0.0073(5) 0.49762(16) 0.0522(8) Uani 1 1 d . . . . .
H33 H 0.258424 -0.085964 0.519932 0.063 Uiso 1 1 calc R U . . .
C34 C 0.29904(10) 0.1195(5) 0.52289(14) 0.0476(8) Uani 1 1 d . . . . .
H34 H 0.305399 0.126295 0.562427 0.057 Uiso 1 1 calc R U . . .
C35 C 0.31770(9) 0.2370(4) 0.48952(12) 0.0381(6) Uani 1 1 d . . . . .
H35 H 0.336433 0.322788 0.506931 0.046 Uiso 1 1 calc R U . . .
P41 P 0.38709(3) 0.38271(14) 0.65958(4) 0.0550(2) Uani 1 1 d . . . . .
F42 F 0.40374(11) 0.3665(5) 0.60179(10) 0.1126(10) Uani 1 1 d . . . . .
F43 F 0.37466(10) 0.4004(4) 0.72031(11) 0.1027(9) Uani 1 1 d . . . . .
F44 F 0.34898(11) 0.4778(6) 0.62792(17) 0.1387(14) Uani 1 1 d . . . . .
F45 F 0.36751(11) 0.1900(4) 0.65010(14) 0.1189(11) Uani 1 1 d . . . . .
F46 F 0.42818(8) 0.2835(4) 0.69154(11) 0.0907(8) Uani 1 1 d . . . . .
F47 F 0.40998(12) 0.5717(4) 0.67112(14) 0.1232(12) Uani 1 1 d . . . . .


_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 N13B 1.91(3) . ?
Cu1 N3 1.947(2) . ?
Cu1 N13 1.954(6) . ?
Cu1 N10B 2.027(15) . ?
Cu1 N10 2.103(3) . ?
Cu1 Cl2 2.3294(7) . ?
Cu1 Cl2 2.7423(8) 5_666 ?
N3 C4 1.315(4) . ?
N3 C7 1.378(4) . ?
C4 N5 1.333(4) . ?
C4 H4 0.9300 . ?
N5 C6 1.350(4) . ?
N5 H5 0.8600 . ?
C6 C7 1.354(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.492(4) . ?
C8 C9 1.497(18) . ?
C8 C9B 1.52(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N10 1.480(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
N10 C11 1.485(4) . ?
N10 H10 0.9800 . ?
C11 C12 1.493(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C16 1.355(5) . ?
C12 N13 1.372(4) . ?
N13 C14 1.318(4) . ?
C14 N15 1.339(4) . ?
C14 H14 0.9300 . ?
N15 C16 1.383(4) . ?
N15 C17 1.505(5) . ?
C16 H16 0.9300 . ?
C9B N10B 1.480(13) . ?
C9B H9C 0.9700 . ?
C9B H9D 0.9700 . ?
N10B C11B 1.485(9) . ?
N10B H10B 0.9800 . ?
C11B C12B 1.495(9) . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?
C12B C16B 1.354(10) . ?
C12B N13B 1.375(9) . ?
N13B C14B 1.320(9) . ?
C14B N15B 1.338(9) . ?
C14B H14B 0.9300 . ?
N15B C16B 1.382(9) . ?
N15B C17 1.55(2) . ?
C16B H16B 0.9300 . ?
C17 C30 1.535(4) . ?
C17 C24 1.545(4) . ?
C17 C18 1.547(4) . ?
C18 C19 1.384(4) . ?
C18 C23 1.391(4) . ?
C19 C20 1.382(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.369(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.370(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.379(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.380(4) . ?
C24 C29 1.386(4) . ?
C25 C26 1.392(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.370(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.372(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.378(4) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 C35 1.381(4) . ?
C30 C31 1.392(4) . ?
C31 C32 1.376(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.374(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.376(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.385(4) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
P41 F44 1.528(3) . ?
P41 F45 1.551(3) . ?
P41 F42 1.571(3) . ?
P41 F43 1.574(2) . ?
P41 F47 1.578(3) . ?
P41 F46 1.619(3) . ?

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
N13B Cu1 N3 169.7(15) . . ?
N3 Cu1 N13 163.5(3) . . ?
N13B Cu1 N10B 83.5(6) . . ?
N3 Cu1 N10B 89.7(4) . . ?
N3 Cu1 N10 93.20(11) . . ?
N13 Cu1 N10 80.12(19) . . ?
N13B Cu1 Cl2 89.9(7) . . ?
N3 Cu1 Cl2 94.50(7) . . ?
N13 Cu1 Cl2 92.53(17) . . ?
N10B Cu1 Cl2 163.1(6) . . ?
N10 Cu1 Cl2 172.29(9) . . ?
N13B Cu1 Cl2 91.9(18) . 5_666 ?
N3 Cu1 Cl2 97.15(7) . 5_666 ?
N13 Cu1 Cl2 97.4(4) . 5_666 ?
N10B Cu1 Cl2 103.1(6) . 5_666 ?
N10 Cu1 Cl2 86.01(14) . 5_666 ?
Cl2 Cu1 Cl2 92.73(2) . 5_666 ?
Cu1 Cl2 Cu1 87.27(2) . 5_666 ?
C4 N3 C7 106.4(2) . . ?
C4 N3 Cu1 127.1(2) . . ?
C7 N3 Cu1 125.92(19) . . ?
N3 C4 N5 110.2(3) . . ?
N3 C4 H4 124.9 . . ?
N5 C4 H4 124.9 . . ?
C4 N5 C6 108.5(3) . . ?
C4 N5 H5 125.8 . . ?
C6 N5 H5 125.8 . . ?
N5 C6 C7 106.5(3) . . ?
N5 C6 H6 126.8 . . ?
C7 C6 H6 126.8 . . ?
C6 C7 N3 108.5(3) . . ?
C6 C7 C8 129.6(3) . . ?
N3 C7 C8 121.9(3) . . ?
C7 C8 C9 113.3(6) . . ?
C7 C8 C9B 113(2) . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
N10 C9 C8 110.3(14) . . ?
N10 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
N10 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C9 N10 C11 111.2(9) . . ?
C9 N10 Cu1 120.6(5) . . ?
C11 N10 Cu1 109.8(3) . . ?
C9 N10 H10 104.6 . . ?
C11 N10 H10 104.6 . . ?
Cu1 N10 H10 104.6 . . ?
N10 C11 C12 108.4(3) . . ?
N10 C11 H11A 110.0 . . ?
C12 C11 H11A 110.0 . . ?
N10 C11 H11B 110.0 . . ?
C12 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
C16 C12 N13 108.6(3) . . ?
C16 C12 C11 134.3(3) . . ?
N13 C12 C11 117.0(3) . . ?
C14 N13 C12 107.1(3) . . ?
C14 N13 Cu1 134.9(5) . . ?
C12 N13 Cu1 116.4(3) . . ?
N13 C14 N15 110.5(3) . . ?
N13 C14 H14 124.7 . . ?
N15 C14 H14 124.7 . . ?
C14 N15 C16 107.3(3) . . ?
C14 N15 C17 126.0(5) . . ?
C16 N15 C17 125.9(5) . . ?
C12 C16 N15 106.4(3) . . ?
C12 C16 H16 126.8 . . ?
N15 C16 H16 126.8 . . ?
N10B C9B C8 119(4) . . ?
N10B C9B H9C 107.6 . . ?
C8 C9B H9C 107.6 . . ?
N10B C9B H9D 107.6 . . ?
C8 C9B H9D 107.6 . . ?
H9C C9B H9D 107.0 . . ?
C9B N10B C11B 111.3(16) . . ?
C9B N10B Cu1 123(3) . . ?
C11B N10B Cu1 109.6(10) . . ?
C9B N10B H10B 103.7 . . ?
C11B N10B H10B 103.7 . . ?
Cu1 N10B H10B 103.7 . . ?
N10B C11B C12B 106.8(10) . . ?
N10B C11B H11C 110.4 . . ?
C12B C11B H11C 110.4 . . ?
N10B C11B H11D 110.4 . . ?
C12B C11B H11D 110.4 . . ?
H11C C11B H11D 108.6 . . ?
C16B C12B N13B 108.3(10) . . ?
C16B C12B C11B 135.2(12) . . ?
N13B C12B C11B 115.8(10) . . ?
C14B N13B C12B 106.6(9) . . ?
C14B N13B Cu1 137(2) . . ?
C12B N13B Cu1 114.9(10) . . ?
N13B C14B N15B 110.4(9) . . ?
N13B C14B H14B 124.8 . . ?
N15B C14B H14B 124.8 . . ?
C14B N15B C16B 107.3(9) . . ?
C14B N15B C17 132(3) . . ?
C16B N15B C17 117(2) . . ?
C12B C16B N15B 105.9(11) . . ?
C12B C16B H16B 127.0 . . ?
N15B C16B H16B 127.0 . . ?
N15 C17 C30 107.5(5) . . ?
N15 C17 C24 105.0(5) . . ?
C30 C17 C24 113.1(2) . . ?
N15 C17 C18 109.6(3) . . ?
C30 C17 C18 107.6(2) . . ?
C24 C17 C18 113.8(2) . . ?
C30 C17 N15B 114(2) . . ?
C24 C17 N15B 106(2) . . ?
C18 C17 N15B 101.5(12) . . ?
C19 C18 C23 117.9(3) . . ?
C19 C18 C17 123.8(3) . . ?
C23 C18 C17 118.3(2) . . ?
C20 C19 C18 120.1(3) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 121.2(3) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 119.5(3) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C21 C22 C23 119.8(3) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C22 C23 C18 121.5(3) . . ?
C22 C23 H23 119.3 . . ?
C18 C23 H23 119.3 . . ?
C25 C24 C29 118.2(3) . . ?
C25 C24 C17 122.8(3) . . ?
C29 C24 C17 118.9(2) . . ?
C24 C25 C26 120.2(3) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C27 C26 C25 120.5(3) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C26 C27 C28 119.8(3) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C27 C28 C29 119.8(3) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 H28 120.1 . . ?
C28 C29 C24 121.4(3) . . ?
C28 C29 H29 119.3 . . ?
C24 C29 H29 119.3 . . ?
C35 C30 C31 118.3(3) . . ?
C35 C30 C17 123.2(2) . . ?
C31 C30 C17 118.3(2) . . ?
C32 C31 C30 120.5(3) . . ?
C32 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C33 C32 C31 120.6(3) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C32 C33 C34 119.5(3) . . ?
C32 C33 H33 120.2 . . ?
C34 C33 H33 120.2 . . ?
C33 C34 C35 120.1(3) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C30 C35 C34 120.9(3) . . ?
C30 C35 H35 119.5 . . ?
C34 C35 H35 119.5 . . ?
F44 P41 F45 92.7(2) . . ?
F44 P41 F42 89.3(2) . . ?
F45 P41 F42 90.33(19) . . ?
F44 P41 F43 95.2(2) . . ?
F45 P41 F43 92.25(19) . . ?
F42 P41 F43 174.66(19) . . ?
F44 P41 F47 91.4(2) . . ?
F45 P41 F47 175.9(2) . . ?
F42 P41 F47 89.26(19) . . ?
F43 P41 F47 87.83(18) . . ?
F44 P41 F46 178.3(2) . . ?
F45 P41 F46 87.87(18) . . ?
F42 P41 F46 89.04(17) . . ?
F43 P41 F46 86.39(16) . . ?
F47 P41 F46 88.00(19) . . ?

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 0.2(4) . . . . ?
Cu1 N3 C4 N5 -171.0(2) . . . . ?
N3 C4 N5 C6 0.0(4) . . . . ?
C4 N5 C6 C7 -0.2(4) . . . . ?
N5 C6 C7 N3 0.3(4) . . . . ?
N5 C6 C7 C8 -179.4(3) . . . . ?
C4 N3 C7 C6 -0.3(4) . . . . ?
Cu1 N3 C7 C6 171.1(2) . . . . ?
C4 N3 C7 C8 179.4(3) . . . . ?
Cu1 N3 C7 C8 -9.2(4) . . . . ?
C6 C7 C8 C9 -126.2(9) . . . . ?
N3 C7 C8 C9 54.2(10) . . . . ?
C6 C7 C8 C9B -129(4) . . . . ?
N3 C7 C8 C9B 52(4) . . . . ?
C7 C8 C9 N10 -70.8(15) . . . . ?
C8 C9 N10 C11 175.9(9) . . . . ?
C8 C9 N10 Cu1 45.3(18) . . . . ?
C9 N10 C11 C12 -163.9(8) . . . . ?
Cu1 N10 C11 C12 -27.9(5) . . . . ?
N10 C11 C12 C16 -168.5(15) . . . . ?
N10 C11 C12 N13 14.7(8) . . . . ?
C16 C12 N13 C14 -2.2(14) . . . . ?
C11 C12 N13 C14 175.4(8) . . . . ?
C16 C12 N13 Cu1 -170.0(12) . . . . ?
C11 C12 N13 Cu1 7.5(10) . . . . ?
C12 N13 C14 N15 1.1(14) . . . . ?
Cu1 N13 C14 N15 165.6(10) . . . . ?
N13 C14 N15 C16 0.4(17) . . . . ?
N13 C14 N15 C17 -170.1(10) . . . . ?
N13 C12 C16 N15 2.4(18) . . . . ?
C11 C12 C16 N15 -174.5(7) . . . . ?
C14 N15 C16 C12 -1.8(19) . . . . ?
C17 N15 C16 C12 168.8(11) . . . . ?
C7 C8 C9B N10B -42(8) . . . . ?
C8 C9B N10B C11B -138(5) . . . . ?
C8 C9B N10B Cu1 -5(9) . . . . ?
C9B N10B C11B C12B 170(5) . . . . ?
Cu1 N10B C11B C12B 31(2) . . . . ?
N10B C11B C12B C16B 137(7) . . . . ?
N10B C11B C12B N13B -31(4) . . . . ?
C16B C12B N13B C14B 11(7) . . . . ?
C11B C12B N13B C14B -177(4) . . . . ?
C16B C12B N13B Cu1 -156(6) . . . . ?
C11B C12B N13B Cu1 15(5) . . . . ?
C12B N13B C14B N15B -6(7) . . . . ?
Cu1 N13B C14B N15B 157(5) . . . . ?
N13B C14B N15B C16B -2(8) . . . . ?
N13B C14B N15B C17 -161(5) . . . . ?
N13B C12B C16B N15B -12(8) . . . . ?
C11B C12B C16B N15B 179(4) . . . . ?
C14B N15B C16B C12B 9(9) . . . . ?
C17 N15B C16B C12B 171(5) . . . . ?
C14 N15 C17 C30 90.0(11) . . . . ?
C16 N15 C17 C30 -78.8(16) . . . . ?
C14 N15 C17 C24 -149.3(10) . . . . ?
C16 N15 C17 C24 41.9(16) . . . . ?
C14 N15 C17 C18 -26.7(12) . . . . ?
C16 N15 C17 C18 164.5(14) . . . . ?
C14B N15B C17 C30 83(6) . . . . ?
C16B N15B C17 C30 -75(6) . . . . ?
C14B N15B C17 C24 -152(6) . . . . ?
C16B N15B C17 C24 50(6) . . . . ?
C14B N15B C17 C18 -33(6) . . . . ?
C16B N15B C17 C18 170(6) . . . . ?
N15 C17 C18 C19 -107.3(6) . . . . ?
C30 C17 C18 C19 136.1(3) . . . . ?
C24 C17 C18 C19 9.9(4) . . . . ?
N15B C17 C18 C19 -104(2) . . . . ?
N15 C17 C18 C23 74.9(6) . . . . ?
C30 C17 C18 C23 -41.7(3) . . . . ?
C24 C17 C18 C23 -167.9(2) . . . . ?
N15B C17 C18 C23 78(2) . . . . ?
C23 C18 C19 C20 -0.8(4) . . . . ?
C17 C18 C19 C20 -178.6(3) . . . . ?
C18 C19 C20 C21 -1.3(5) . . . . ?
C19 C20 C21 C22 1.7(5) . . . . ?
C20 C21 C22 C23 -0.1(5) . . . . ?
C21 C22 C23 C18 -2.0(5) . . . . ?
C19 C18 C23 C22 2.4(4) . . . . ?
C17 C18 C23 C22 -179.6(3) . . . . ?
N15 C17 C24 C25 -122.7(4) . . . . ?
C30 C17 C24 C25 -5.7(4) . . . . ?
C18 C17 C24 C25 117.4(3) . . . . ?
N15B C17 C24 C25 -131.6(17) . . . . ?
N15 C17 C24 C29 54.5(5) . . . . ?
C30 C17 C24 C29 171.4(3) . . . . ?
C18 C17 C24 C29 -65.4(3) . . . . ?
N15B C17 C24 C29 45.6(17) . . . . ?
C29 C24 C25 C26 0.6(4) . . . . ?
C17 C24 C25 C26 177.8(3) . . . . ?
C24 C25 C26 C27 0.5(5) . . . . ?
C25 C26 C27 C28 -0.8(5) . . . . ?
C26 C27 C28 C29 0.1(6) . . . . ?
C27 C28 C29 C24 1.1(5) . . . . ?
C25 C24 C29 C28 -1.4(5) . . . . ?
C17 C24 C29 C28 -178.7(3) . . . . ?
N15 C17 C30 C35 -0.3(5) . . . . ?
C24 C17 C30 C35 -115.8(3) . . . . ?
C18 C17 C30 C35 117.7(3) . . . . ?
N15B C17 C30 C35 6.0(16) . . . . ?
N15 C17 C30 C31 -176.1(4) . . . . ?
C24 C17 C30 C31 68.5(3) . . . . ?
C18 C17 C30 C31 -58.1(3) . . . . ?
N15B C17 C30 C31 -169.8(15) . . . . ?
C35 C30 C31 C32 2.0(4) . . . . ?
C17 C30 C31 C32 178.0(3) . . . . ?
C30 C31 C32 C33 -2.1(5) . . . . ?
C31 C32 C33 C34 0.9(5) . . . . ?
C32 C33 C34 C35 0.3(5) . . . . ?
C31 C30 C35 C34 -0.8(4) . . . . ?
C17 C30 C35 C34 -176.6(3) . . . . ?
C33 C34 C35 C30 -0.4(5) . . . . ?

_refine_diff_density_max         0.497
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.068



_exptl_crystal_recrystallization_method 
'diffusion of diethyl ether in a methanol solution of the compound'
