# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_L1
_database_code_depnum_ccdc_archive 'CCDC 2289693'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2023-08-20 deposited with the CCDC.	2024-01-04 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         'C23 H38 N8'
_chemical_formula_sum            'C23 H38 N8'
_chemical_formula_weight         426.61

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'

_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                   8.624(3)
_cell_length_b                   9.128(3)
_cell_length_c                   15.701(5)
_cell_angle_alpha                76.082(6)
_cell_angle_beta                 85.831(6)
_cell_angle_gamma                77.379(6)
_cell_volume                     1170.6(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    650
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      21.59

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6599
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   
'SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         microsource
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13304
_diffrn_reflns_av_unetI/netI     0.1023
_diffrn_reflns_av_R_equivalents  0.0913
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.350
_diffrn_reflns_theta_max         25.479
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4333
_reflns_number_gt                2512
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT V8.34A'
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0463P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0077(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4333
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1145
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1147
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_restrained_S_all      0.934
_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
C1 C 0.6950(3) 0.3483(3) 0.93934(18) 0.0299(7) Uani 1 1 d . . . . .
N1 N 0.5469(3) 0.3807(2) 0.92161(14) 0.0266(5) Uani 1 1 d . . . . .
C2 C 0.9571(3) 0.3967(4) 0.8803(2) 0.0456(9) Uani 1 1 d . . . . .
H2A H 0.974417 0.286855 0.880620 0.068 Uiso 1 1 calc R U . . .
H2B H 1.036954 0.413066 0.916410 0.068 Uiso 1 1 calc R U . . .
H2C H 0.966388 0.456405 0.819956 0.068 Uiso 1 1 calc R U . . .
N2 N 0.8011(3) 0.4464(3) 0.91531(16) 0.0367(6) Uani 1 1 d . . . . .
C3 C 0.7575(3) 0.6076(3) 0.92210(19) 0.0391(8) Uani 1 1 d . . . . .
H3A H 0.739941 0.675025 0.863312 0.059 Uiso 1 1 calc R U . . .
H3B H 0.843496 0.632741 0.949723 0.059 Uiso 1 1 calc R U . . .
H3C H 0.659856 0.622758 0.957820 0.059 Uiso 1 1 calc R U . . .
N3 N 0.7653(3) 0.1988(3) 0.98427(15) 0.0337(6) Uani 1 1 d . . . . .
C4 C 0.8673(3) 0.1811(4) 1.05795(19) 0.0418(8) Uani 1 1 d . . . . .
H4A H 0.956699 0.093631 1.058395 0.063 Uiso 1 1 calc R U . . .
H4B H 0.805893 0.162280 1.113053 0.063 Uiso 1 1 calc R U . . .
H4C H 0.907874 0.275444 1.051834 0.063 Uiso 1 1 calc R U . . .
N4 N 0.3857(2) 0.3899(2) 0.75634(13) 0.0193(5) Uani 1 1 d . . . . .
C5 C 0.6685(3) 0.0826(3) 0.99909(19) 0.0369(8) Uani 1 1 d . . . . .
H5A H 0.619918 0.086038 0.943960 0.055 Uiso 1 1 calc R U . . .
H5B H 0.584983 0.103314 1.042961 0.055 Uiso 1 1 calc R U . . .
H5C H 0.735530 -0.019736 1.020347 0.055 Uiso 1 1 calc R U . . .
N5 N 0.2610(2) 0.6704(2) 0.55562(14) 0.0233(5) Uani 1 1 d . . . . .
C7 C 0.4863(3) 0.5221(3) 0.85545(17) 0.0277(7) Uani 1 1 d . . . . .
H7A H 0.571926 0.544624 0.811904 0.033 Uiso 1 1 calc R U . . .
H7AB H 0.454496 0.609721 0.884280 0.033 Uiso 1 1 calc R U . . .
N7 N 0.3954(2) 0.0097(2) 0.74267(14) 0.0239(5) Uani 1 1 d . . . . .
N6 N 0.7500(2) 0.6736(2) 0.53351(14) 0.0238(5) Uani 1 1 d . . . . .
C8 C 0.3455(3) 0.5068(3) 0.80889(17) 0.0254(6) Uani 1 1 d . . . . .
H8A H 0.262372 0.479288 0.853023 0.030 Uiso 1 1 calc R U . . .
H8AB H 0.300834 0.607810 0.769978 0.030 Uiso 1 1 calc R U . . .
N8 N 0.8904(3) -0.0177(3) 0.71878(15) 0.0304(6) Uani 1 1 d . . . . .
C9 C 0.3046(3) 0.4384(3) 0.67253(16) 0.0224(6) Uani 1 1 d . . . . .
H9A H 0.190060 0.476785 0.683158 0.027 Uiso 1 1 calc R U . . .
H9AB H 0.315182 0.347783 0.646681 0.027 Uiso 1 1 calc R U . . .
C10 C 0.3694(3) 0.5630(3) 0.60761(16) 0.0214(6) Uani 1 1 d . . . . .
C11 C 0.5303(3) 0.5594(3) 0.60195(16) 0.0205(6) Uani 1 1 d . . . . .
H11 H 0.600319 0.479727 0.640009 0.025 Uiso 1 1 calc R U . . .
C12 C 0.5911(3) 0.6728(3) 0.54030(16) 0.0215(6) Uani 1 1 d . . . . .
C13 C 0.4790(3) 0.7869(3) 0.48656(16) 0.0234(6) Uani 1 1 d . . . . .
H13 H 0.511982 0.868209 0.444155 0.028 Uiso 1 1 calc R U . . .
C14 C 0.3214(3) 0.7787(3) 0.49640(17) 0.0246(6) Uani 1 1 d . . . . .
H14 H 0.248746 0.855654 0.458386 0.029 Uiso 1 1 calc R U . . .
C15 C 0.8615(3) 0.5487(3) 0.58712(18) 0.0278(7) Uani 1 1 d . . . . .
H15A H 0.854709 0.450611 0.573997 0.042 Uiso 1 1 calc R U . . .
H15B H 0.835390 0.544662 0.649324 0.042 Uiso 1 1 calc R U . . .
H15C H 0.969669 0.566435 0.574203 0.042 Uiso 1 1 calc R U . . .
C16 C 0.8093(3) 0.7999(3) 0.47475(18) 0.0299(7) Uani 1 1 d . . . . .
H16A H 0.788056 0.802318 0.413910 0.045 Uiso 1 1 calc R U . . .
H16B H 0.924103 0.784670 0.481957 0.045 Uiso 1 1 calc R U . . .
H16C H 0.755795 0.897808 0.488838 0.045 Uiso 1 1 calc R U . . .
C17 C 0.3609(3) 0.2373(3) 0.80408(16) 0.0223(6) Uani 1 1 d . . . . .
H17A H 0.248251 0.232159 0.800059 0.027 Uiso 1 1 calc R U . . .
H17B H 0.384616 0.221038 0.866816 0.027 Uiso 1 1 calc R U . . .
C18 C 0.4667(3) 0.1115(3) 0.76652(16) 0.0200(6) Uani 1 1 d . . . . .
C19 C 0.6276(3) 0.1073(3) 0.75855(16) 0.0225(6) Uani 1 1 d . . . . .
H19 H 0.669501 0.183523 0.775760 0.027 Uiso 1 1 calc R U . . .
C20 C 0.7302(3) -0.0089(3) 0.72519(16) 0.0231(6) Uani 1 1 d . . . . .
C21 C 0.6562(3) -0.1143(3) 0.69966(16) 0.0256(6) Uani 1 1 d . . . . .
H21 H 0.717997 -0.195121 0.675652 0.031 Uiso 1 1 calc R U . . .
C22 C 0.4948(3) -0.0999(3) 0.70961(17) 0.0262(6) Uani 1 1 d . . . . .
H22 H 0.449270 -0.173240 0.691727 0.031 Uiso 1 1 calc R U . . .
C23 C 0.9948(3) -0.1346(3) 0.6813(2) 0.0380(8) Uani 1 1 d . . . . .
H23A H 0.971592 -0.117041 0.619092 0.057 Uiso 1 1 calc R U . . .
H23B H 0.977938 -0.236893 0.712408 0.057 Uiso 1 1 calc R U . . .
H23C H 1.105631 -0.129067 0.687236 0.057 Uiso 1 1 calc R U . . .
C24 C 0.9571(3) 0.0980(3) 0.74402(18) 0.0301(7) Uani 1 1 d . . . . .
H24A H 1.073335 0.069746 0.740934 0.045 Uiso 1 1 calc R U . . .
H24B H 0.922405 0.104007 0.804153 0.045 Uiso 1 1 calc R U . . .
H24C H 0.920501 0.198507 0.704028 0.045 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.282(3) . ?
C1 N2 1.388(3) . ?
C1 N3 1.402(3) . ?
N1 C7 1.469(3) . ?
C2 N2 1.437(3) . ?
N2 C3 1.465(4) . ?
N3 C5 1.454(3) . ?
N3 C4 1.461(3) . ?
N4 C9 1.461(3) . ?
N4 C17 1.468(3) . ?
N4 C8 1.469(3) . ?
N5 C14 1.351(3) . ?
N5 C10 1.352(3) . ?
C7 C8 1.510(3) . ?
N7 C22 1.348(3) . ?
N7 C18 1.354(3) . ?
N6 C12 1.368(3) . ?
N6 C15 1.453(3) . ?
N6 C16 1.456(3) . ?
N8 C20 1.364(3) . ?
N8 C23 1.450(3) . ?
N8 C24 1.450(3) . ?
C9 C10 1.511(3) . ?
C10 C11 1.378(3) . ?
C11 C12 1.402(3) . ?
C12 C13 1.410(3) . ?
C13 C14 1.373(3) . ?
C17 C18 1.512(3) . ?
C18 C19 1.377(3) . ?
C19 C20 1.404(3) . ?
C20 C21 1.409(3) . ?
C21 C22 1.370(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 126.5(3) . . ?
N1 C1 N3 119.7(2) . . ?
N2 C1 N3 113.7(2) . . ?
C1 N1 C7 118.3(2) . . ?
C1 N2 C2 121.9(3) . . ?
C1 N2 C3 121.5(2) . . ?
C2 N2 C3 116.6(2) . . ?
C1 N3 C5 117.0(2) . . ?
C1 N3 C4 118.4(2) . . ?
C5 N3 C4 112.9(2) . . ?
C9 N4 C17 110.68(19) . . ?
C9 N4 C8 112.64(19) . . ?
C17 N4 C8 113.32(19) . . ?
C14 N5 C10 114.9(2) . . ?
N1 C7 C8 111.6(2) . . ?
C22 N7 C18 114.8(2) . . ?
C12 N6 C15 119.8(2) . . ?
C12 N6 C16 121.0(2) . . ?
C15 N6 C16 119.2(2) . . ?
N4 C8 C7 113.2(2) . . ?
C20 N8 C23 121.2(2) . . ?
C20 N8 C24 119.7(2) . . ?
C23 N8 C24 119.0(2) . . ?
N4 C9 C10 113.0(2) . . ?
N5 C10 C11 124.1(2) . . ?
N5 C10 C9 115.7(2) . . ?
C11 C10 C9 120.2(2) . . ?
C10 C11 C12 120.3(2) . . ?
N6 C12 C11 121.8(2) . . ?
N6 C12 C13 122.0(2) . . ?
C11 C12 C13 116.2(2) . . ?
C14 C13 C12 119.0(2) . . ?
N5 C14 C13 125.5(2) . . ?
N4 C17 C18 110.8(2) . . ?
N7 C18 C19 124.2(2) . . ?
N7 C18 C17 117.1(2) . . ?
C19 C18 C17 118.7(2) . . ?
C18 C19 C20 120.5(2) . . ?
N8 C20 C19 121.5(2) . . ?
N8 C20 C21 123.0(2) . . ?
C19 C20 C21 115.5(2) . . ?
C22 C21 C20 119.7(2) . . ?
N7 C22 C21 125.4(2) . . ?

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
N2 C1 N1 C7 13.2(4) . . . . ?
N3 C1 N1 C7 -163.9(2) . . . . ?
N1 C1 N2 C2 -135.2(3) . . . . ?
N3 C1 N2 C2 42.1(4) . . . . ?
N1 C1 N2 C3 43.0(4) . . . . ?
N3 C1 N2 C3 -139.7(3) . . . . ?
N1 C1 N3 C5 7.3(4) . . . . ?
N2 C1 N3 C5 -170.3(2) . . . . ?
N1 C1 N3 C4 -133.3(3) . . . . ?
N2 C1 N3 C4 49.1(3) . . . . ?
C1 N1 C7 C8 151.0(2) . . . . ?
C9 N4 C8 C7 -140.2(2) . . . . ?
C17 N4 C8 C7 93.2(3) . . . . ?
N1 C7 C8 N4 -65.1(3) . . . . ?
C17 N4 C9 C10 -159.9(2) . . . . ?
C8 N4 C9 C10 72.1(3) . . . . ?
C14 N5 C10 C11 -0.7(3) . . . . ?
C14 N5 C10 C9 -178.3(2) . . . . ?
N4 C9 C10 N5 -143.7(2) . . . . ?
N4 C9 C10 C11 38.5(3) . . . . ?
N5 C10 C11 C12 0.9(4) . . . . ?
C9 C10 C11 C12 178.4(2) . . . . ?
C15 N6 C12 C11 4.2(4) . . . . ?
C16 N6 C12 C11 -174.3(2) . . . . ?
C15 N6 C12 C13 -176.6(2) . . . . ?
C16 N6 C12 C13 4.9(4) . . . . ?
C10 C11 C12 N6 179.3(2) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
N6 C12 C13 C14 179.6(2) . . . . ?
C11 C12 C13 C14 -1.2(3) . . . . ?
C10 N5 C14 C13 -0.5(4) . . . . ?
C12 C13 C14 N5 1.5(4) . . . . ?
C9 N4 C17 C18 77.6(2) . . . . ?
C8 N4 C17 C18 -154.7(2) . . . . ?
C22 N7 C18 C19 0.1(3) . . . . ?
C22 N7 C18 C17 180.0(2) . . . . ?
N4 C17 C18 N7 -126.6(2) . . . . ?
N4 C17 C18 C19 53.3(3) . . . . ?
N7 C18 C19 C20 -1.0(4) . . . . ?
C17 C18 C19 C20 179.1(2) . . . . ?
C23 N8 C20 C19 -177.8(2) . . . . ?
C24 N8 C20 C19 -2.1(4) . . . . ?
C23 N8 C20 C21 2.6(4) . . . . ?
C24 N8 C20 C21 178.2(2) . . . . ?
C18 C19 C20 N8 -178.3(2) . . . . ?
C18 C19 C20 C21 1.4(4) . . . . ?
N8 C20 C21 C22 178.7(2) . . . . ?
C19 C20 C21 C22 -1.0(4) . . . . ?
C18 N7 C22 C21 0.4(4) . . . . ?
C20 C21 C22 N7 0.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3C N1 0.98 2.50 3.463(4) 166.0 2_667 yes
C17 H17B N1 0.99 2.55 3.195(3) 122.8 . yes

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.053


####################################################################### 
# 
# 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_C5
_database_code_depnum_ccdc_archive 'CCDC 2289698'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2023-08-20 deposited with the CCDC.	2024-01-04 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         'C21 H48 Cu N10, Br [+C7 H8]'
_chemical_formula_sum            'C21 H48 Br Cu N10 [+C7 H8]'
_chemical_formula_weight         584.14

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   11.8799(17)
_cell_length_b                   11.8799(17)
_cell_length_c                   35.794(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4374.9(15)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    21239
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      33.62

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             1848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.146
_shelx_estimated_absorpt_T_min   0.661
_shelx_estimated_absorpt_T_max   0.783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270. Afterwards scaling of
reflection intensities was performed within STOE LANA. J. Koziskova, F. Hahn,
J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136-140.
;
_exptl_absorpt_correction_T_min  0.1002
_exptl_absorpt_correction_T_max  0.7836

_exptl_absorpt_special_details   ?
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'

_diffrn_detector                 Pilatus200K
_diffrn_detector_type            'DECTRIS PILATUS 200K'
_diffrn_detector_area_resol_mean 5.81

_diffrn_source                   'Genix Mo'
_diffrn_source_type              ?
_diffrn_radiation_probe          x-ray
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'

_diffrn_ambient_temperature      100

_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 1178 frames, detector distance = 60 mm
;

_diffrn_reflns_number            33104
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.283
_diffrn_reflns_theta_max         34.073
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3801
_reflns_number_gt                2716
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       
;
X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)
;
_computing_cell_refinement       
;
X-Area Recipe 1.36.0.0 (STOE, 2020)
;
_computing_data_reduction        
;
X-Area Integrate 1.78.3.0 (STOE, 2020)
X-Area LANA 1.83.8.0 (STOE, 2020)
;

_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.90, Darmstadt 2020
;

_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)+(0.0366P)²+4.1652P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         3801
_refine_ls_number_parameters     104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0818
_refine_ls_wR_factor_gt          0.0740
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.002
_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 0.333333 0.666667 0.38218(2) 0.01175(8) Uani 1 3 d S T P . .
N1 N 0.32495(13) 0.49078(13) 0.37628(3) 0.0139(2) Uani 1 1 d . . . . .
C1 C 0.33013(15) 0.41387(15) 0.40138(4) 0.0138(3) Uani 1 1 d . . . . .
N2 N 0.39314(13) 0.34397(13) 0.39623(4) 0.0152(3) Uani 1 1 d . . . . .
C2 C 0.52572(16) 0.40771(17) 0.38222(5) 0.0192(3) Uani 1 1 d . . . . .
H2A H 0.527780 0.369383 0.358164 0.029 Uiso 1 1 calc R U . . .
H2B H 0.581445 0.396028 0.400128 0.029 Uiso 1 1 calc R U . . .
H2C H 0.557316 0.500693 0.378918 0.029 Uiso 1 1 calc R U . . .
N3 N 0.26643(15) 0.39434(14) 0.43486(4) 0.0184(3) Uani 1 1 d . . . . .
C3 C 0.35147(17) 0.21969(16) 0.41470(4) 0.0187(3) Uani 1 1 d . . . . .
H3A H 0.355279 0.158955 0.396916 0.028 Uiso 1 1 calc R U . . .
H3B H 0.262110 0.183937 0.423704 0.028 Uiso 1 1 calc R U . . .
H3C H 0.409052 0.232746 0.435874 0.028 Uiso 1 1 calc R U . . .
N4 N 0.333333 0.666667 0.32072(6) 0.0116(4) Uani 1 3 d S T P . .
C4 C 0.1675(2) 0.4311(2) 0.43829(5) 0.0261(4) Uani 1 1 d . . . . .
H4A H 0.208940 0.524645 0.443139 0.039 Uiso 1 1 calc R U . . .
H4B H 0.109176 0.383162 0.459026 0.039 Uiso 1 1 calc R U . . .
H4C H 0.117451 0.410336 0.415040 0.039 Uiso 1 1 calc R U . . .
C5 C 0.3323(2) 0.39729(19) 0.46979(4) 0.0273(4) Uani 1 1 d . . . . .
H5A H 0.415244 0.402046 0.464099 0.041 Uiso 1 1 calc R U . . .
H5B H 0.277323 0.318231 0.484176 0.041 Uiso 1 1 calc R U . . .
H5C H 0.348305 0.473585 0.484448 0.041 Uiso 1 1 calc R U . . .
C6 C 0.29374(15) 0.53186(15) 0.31106(4) 0.0139(3) Uani 1 1 d . . . . .
H6A H 0.320126 0.528275 0.285056 0.017 Uiso 1 1 calc R U . . .
H6B H 0.197926 0.477740 0.312585 0.017 Uiso 1 1 calc R U . . .
C7 C 0.35587(16) 0.47740(16) 0.33747(4) 0.0144(3) Uani 1 1 d . . . . .
H7A H 0.322864 0.384562 0.331710 0.017 Uiso 1 1 calc R U . . .
H7B H 0.451306 0.524976 0.333927 0.017 Uiso 1 1 calc R U . . .
Br1 Br 0.333333 0.666667 0.52926(2) 0.02070(8) Uani 1 3 d S T P . .


_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 N1 2.0525(14) 3_565 ?
Cu1 N1 2.0525(14) 2_665 ?
Cu1 N1 2.0525(14) . ?
Cu1 N4 2.200(2) . ?
N1 C1 1.3047(19) . ?
N1 C7 1.4658(19) . ?
C1 N3 1.3735(19) . ?
C1 N2 1.380(2) . ?
N2 C2 1.454(2) . ?
N2 C3 1.460(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N3 C4 1.449(2) . ?
N3 C5 1.466(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
N4 C6 1.4670(16) 3_565 ?
N4 C6 1.4670(16) . ?
N4 C6 1.4670(16) 2_665 ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.528(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

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
N1 Cu1 N1 118.955(12) 3_565 2_665 ?
N1 Cu1 N1 118.955(12) 3_565 . ?
N1 Cu1 N1 118.953(12) 2_665 . ?
N1 Cu1 N4 84.09(3) 3_565 . ?
N1 Cu1 N4 84.09(3) 2_665 . ?
N1 Cu1 N4 84.09(3) . . ?
C1 N1 C7 118.34(13) . . ?
C1 N1 Cu1 130.30(10) . . ?
C7 N1 Cu1 108.71(9) . . ?
N1 C1 N3 120.28(14) . . ?
N1 C1 N2 123.97(14) . . ?
N3 C1 N2 115.70(13) . . ?
C1 N2 C2 120.33(13) . . ?
C1 N2 C3 122.42(13) . . ?
C2 N2 C3 114.47(13) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 N3 C4 118.98(13) . . ?
C1 N3 C5 119.84(15) . . ?
C4 N3 C5 115.08(14) . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C6 N4 C6 114.63(7) 3_565 . ?
C6 N4 C6 114.63(7) 3_565 2_665 ?
C6 N4 C6 114.63(7) . 2_665 ?
C6 N4 Cu1 103.63(10) 3_565 . ?
C6 N4 Cu1 103.63(10) . . ?
C6 N4 Cu1 103.63(10) 2_665 . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C6 C7 110.94(12) . . ?
N4 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
N4 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.0 . . ?
N1 C7 C6 109.88(12) . . ?
N1 C7 H7A 109.7 . . ?
C6 C7 H7A 109.7 . . ?
N1 C7 H7B 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?

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 N1 C1 N3 -160.36(14) . . . . ?
Cu1 N1 C1 N3 40.4(2) . . . . ?
C7 N1 C1 N2 17.0(2) . . . . ?
Cu1 N1 C1 N2 -142.22(13) . . . . ?
N1 C1 N2 C2 49.3(2) . . . . ?
N3 C1 N2 C2 -133.15(15) . . . . ?
N1 C1 N2 C3 -150.57(15) . . . . ?
N3 C1 N2 C3 26.9(2) . . . . ?
N1 C1 N3 C4 16.0(2) . . . . ?
N2 C1 N3 C4 -161.58(16) . . . . ?
N1 C1 N3 C5 -135.16(16) . . . . ?
N2 C1 N3 C5 47.2(2) . . . . ?
C6 N4 C6 C7 -151.46(14) 3_565 . . . ?
C6 N4 C6 C7 72.9(2) 2_665 . . . ?
Cu1 N4 C6 C7 -39.26(12) . . . . ?
C1 N1 C7 C6 157.21(14) . . . . ?
Cu1 N1 C7 C6 -39.36(14) . . . . ?
N4 C6 C7 N1 55.12(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5C Br1 0.98 2.88 3.8382(19) 167.2 . yes

_refine_diff_density_max         0.536
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.087








####################################################################### 
# 
# 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_C2
_database_code_depnum_ccdc_archive 'CCDC 2289695'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2023-08-20 deposited with the CCDC.	2024-01-04 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         'C23 H38 Cl Cu N8, Cl'
_chemical_formula_sum            'C23 H38 Cl2 Cu N8'
_chemical_formula_weight         561.05

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'
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                   8.2624(17)
_cell_length_b                   22.189(4)
_cell_length_c                   14.293(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.53(3)
_cell_angle_gamma                90
_cell_volume                     2608.2(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    43829
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      33.15

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             1180
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.071
_shelx_estimated_absorpt_T_min   0.847
_shelx_estimated_absorpt_T_max   0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270. Afterwards scaling of
reflection intensities was performed within STOE LANA. J. Koziskova, F. Hahn,
J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136-140.
;
_exptl_absorpt_correction_T_min  0.4463
_exptl_absorpt_correction_T_max  0.8949

_exptl_absorpt_special_details   ?
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'

_diffrn_detector                 Pilatus200K
_diffrn_detector_type            'DECTRIS PILATUS 200K'
_diffrn_detector_area_resol_mean 5.81

_diffrn_source                   'Genix Mo'
_diffrn_source_type              ?
_diffrn_radiation_probe          x-ray
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'

_diffrn_ambient_temperature      100

_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 3056 frames, detector distance = 80 mm
;

_diffrn_reflns_number            67965
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.739
_diffrn_reflns_theta_max         33.340
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9614
_reflns_number_gt                6949
_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       
;
X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)
;
_computing_cell_refinement       
;
X-Area Recipe 1.36.0.0 (STOE, 2020)
;
_computing_data_reduction        
;
X-Area Integrate 1.78.3.0 (STOE, 2020)
X-Area LANA 1.83.8.0 (STOE, 2020)
;

_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.90, Darmstadt 2020
;

_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)+(0.0421P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         9614
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0780
_refine_ls_wR_factor_gt          0.0754
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_restrained_S_all      0.944
_refine_ls_shift/su_max          0.002
_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 0.56508(2) 0.47384(2) 0.66610(2) 0.01260(4) Uani 1 1 d . . . . .
Cl1 Cl 0.32271(3) 0.50542(2) 0.71300(2) 0.01743(7) Uani 1 1 d . . . . .
N1 N 0.66813(12) 0.42005(5) 0.78684(7) 0.0149(2) Uani 1 1 d . . . . .
C1 C 0.61369(15) 0.41028(6) 0.86835(9) 0.0153(2) Uani 1 1 d . . . . .
Cl2 Cl -0.08766(5) 0.25962(2) 0.53498(3) 0.03628(10) Uani 1 1 d . . . . .
N2 N 0.46019(13) 0.38868(5) 0.87195(8) 0.0177(2) Uani 1 1 d . . . . .
C2 C 0.35481(18) 0.40674(8) 0.94217(11) 0.0293(3) Uani 1 1 d . . . . .
H2A H 0.254966 0.424410 0.911136 0.044 Uiso 1 1 calc R U . . .
H2B H 0.410686 0.436618 0.984227 0.044 Uiso 1 1 calc R U . . .
H2C H 0.327413 0.371434 0.978695 0.044 Uiso 1 1 calc R U . . .
N3 N 0.70092(14) 0.41916(5) 0.95393(8) 0.0200(2) Uani 1 1 d . . . . .
C3 C 0.37868(16) 0.35427(6) 0.79463(10) 0.0218(3) Uani 1 1 d . . . . .
H3A H 0.330804 0.317849 0.819274 0.033 Uiso 1 1 calc R U . . .
H3B H 0.457605 0.342867 0.750807 0.033 Uiso 1 1 calc R U . . .
H3C H 0.292690 0.378898 0.761711 0.033 Uiso 1 1 calc R U . . .
N4 N 0.78360(12) 0.45103(5) 0.61274(7) 0.0133(2) Uani 1 1 d . . . . .
C4 C 0.68573(19) 0.38099(8) 1.03550(10) 0.0273(3) Uani 1 1 d . . . . .
H4A H 0.652161 0.405544 1.087247 0.041 Uiso 1 1 calc R U . . .
H4B H 0.790750 0.362010 1.054839 0.041 Uiso 1 1 calc R U . . .
H4C H 0.604042 0.349714 1.019313 0.041 Uiso 1 1 calc R U . . .
N5 N 0.69281(12) 0.54686(5) 0.71207(7) 0.0134(2) Uani 1 1 d . . . . .
C5 C 0.82788(18) 0.46427(7) 0.96735(11) 0.0266(3) Uani 1 1 d . . . . .
H5A H 0.825789 0.482763 1.029495 0.040 Uiso 1 1 calc R U . . .
H5B H 0.809832 0.495346 0.918740 0.040 Uiso 1 1 calc R U . . .
H5C H 0.933873 0.445222 0.962905 0.040 Uiso 1 1 calc R U . . .
N6 N 1.01340(13) 0.68333(5) 0.81147(8) 0.0178(2) Uani 1 1 d . . . . .
C6 C 0.84415(14) 0.55101(6) 0.68498(8) 0.0130(2) Uani 1 1 d . . . . .
N7 N 0.47480(12) 0.41701(5) 0.56581(7) 0.0149(2) Uani 1 1 d . . . . .
C7 C 0.95341(15) 0.59514(6) 0.71576(9) 0.0149(2) Uani 1 1 d . . . . .
H7 H 1.058178 0.596114 0.693648 0.018 Uiso 1 1 calc R U . . .
N8 N 0.36348(13) 0.27525(5) 0.37757(8) 0.0195(2) Uani 1 1 d . . . . .
C8 C 0.90953(15) 0.63909(6) 0.78042(9) 0.0146(2) Uani 1 1 d . . . . .
C9 C 0.75161(15) 0.63392(6) 0.81005(9) 0.0158(2) Uani 1 1 d . . . . .
H9 H 0.715527 0.661669 0.854206 0.019 Uiso 1 1 calc R U . . .
C10 C 0.65108(15) 0.58856(6) 0.77454(9) 0.0159(2) Uani 1 1 d . . . . .
H10 H 0.545294 0.586250 0.795110 0.019 Uiso 1 1 calc R U . . .
C11 C 1.16688(15) 0.69118(6) 0.77051(10) 0.0195(3) Uani 1 1 d . . . . .
H11A H 1.231957 0.722107 0.805662 0.029 Uiso 1 1 calc R U . . .
H11B H 1.145177 0.703730 0.704757 0.029 Uiso 1 1 calc R U . . .
H11C H 1.226698 0.652982 0.773561 0.029 Uiso 1 1 calc R U . . .
C12 C 0.96788(18) 0.72776(7) 0.87930(11) 0.0243(3) Uani 1 1 d . . . . .
H12A H 1.056428 0.756894 0.891980 0.036 Uiso 1 1 calc R U . . .
H12B H 0.947371 0.707415 0.937852 0.036 Uiso 1 1 calc R U . . .
H12C H 0.869213 0.748866 0.853667 0.036 Uiso 1 1 calc R U . . .
C13 C 0.58387(15) 0.39515(6) 0.50952(9) 0.0149(2) Uani 1 1 d . . . . .
C14 C 0.55120(15) 0.34895(6) 0.44690(9) 0.0160(2) Uani 1 1 d . . . . .
H14 H 0.633266 0.335258 0.409805 0.019 Uiso 1 1 calc R U . . .
C15 C 0.39618(15) 0.32161(6) 0.43722(9) 0.0145(2) Uani 1 1 d . . . . .
C16 C 0.28153(14) 0.34486(6) 0.49550(9) 0.0149(2) Uani 1 1 d . . . . .
H16 H 0.174686 0.328677 0.492232 0.018 Uiso 1 1 calc R U . . .
C17 C 0.32597(14) 0.39083(6) 0.55654(9) 0.0154(2) Uani 1 1 d . . . . .
H17 H 0.246977 0.405372 0.595060 0.018 Uiso 1 1 calc R U . . .
C18 C 0.48379(17) 0.25504(7) 0.31684(11) 0.0247(3) Uani 1 1 d . . . . .
H18A H 0.434397 0.225463 0.271843 0.037 Uiso 1 1 calc R U . . .
H18B H 0.575315 0.236432 0.355007 0.037 Uiso 1 1 calc R U . . .
H18C H 0.522844 0.289593 0.282699 0.037 Uiso 1 1 calc R U . . .
C19 C 0.21150(16) 0.24212(6) 0.37282(10) 0.0213(3) Uani 1 1 d . . . . .
H19A H 0.232392 0.199334 0.361935 0.032 Uiso 1 1 calc R U . . .
H19B H 0.136887 0.257867 0.321117 0.032 Uiso 1 1 calc R U . . .
H19C H 0.162572 0.246779 0.432191 0.032 Uiso 1 1 calc R U . . .
C20 C 0.85913(15) 0.40280(6) 0.67510(9) 0.0164(2) Uani 1 1 d . . . . .
H20A H 0.975739 0.399098 0.665374 0.020 Uiso 1 1 calc R U . . .
H20B H 0.805871 0.363780 0.658359 0.020 Uiso 1 1 calc R U . . .
C21 C 0.84255(15) 0.41672(6) 0.77726(9) 0.0165(2) Uani 1 1 d . . . . .
H21A H 0.893658 0.384591 0.818115 0.020 Uiso 1 1 calc R U . . .
H21B H 0.895836 0.455544 0.795253 0.020 Uiso 1 1 calc R U . . .
C22 C 0.88706(14) 0.50565(6) 0.61310(9) 0.0143(2) Uani 1 1 d . . . . .
H22A H 0.874085 0.524417 0.549984 0.017 Uiso 1 1 calc R U . . .
H22B H 1.002491 0.493860 0.626674 0.017 Uiso 1 1 calc R U . . .
C23 C 0.74546(15) 0.42664(6) 0.51659(9) 0.0173(3) Uani 1 1 d . . . . .
H23A H 0.831288 0.397936 0.502054 0.021 Uiso 1 1 calc R U . . .
H23B H 0.742416 0.459908 0.470296 0.021 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N7 1.9986(11) . ?
Cu1 N5 2.0093(11) . ?
Cu1 N4 2.0888(11) . ?
Cu1 N1 2.2009(11) . ?
Cu1 Cl1 2.2824(6) . ?
N1 C1 1.3069(17) . ?
N1 C21 1.4626(16) . ?
C1 N2 1.3613(17) . ?
C1 N3 1.3728(17) . ?
N2 C2 1.4473(18) . ?
N2 C3 1.4541(18) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N3 C5 1.4493(19) . ?
N3 C4 1.4562(18) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
N4 C23 1.4824(16) . ?
N4 C22 1.4828(16) . ?
N4 C20 1.4907(16) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N5 C6 1.3473(15) . ?
N5 C10 1.3534(16) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
N6 C8 1.3505(16) . ?
N6 C12 1.4572(17) . ?
N6 C11 1.4576(17) . ?
C6 C7 1.3751(17) . ?
C6 C22 1.5047(18) . ?
N7 C13 1.3544(16) . ?
N7 C17 1.3550(16) . ?
C7 C8 1.4145(18) . ?
C7 H7 0.9500 . ?
N8 C15 1.3467(17) . ?
N8 C19 1.4510(17) . ?
N8 C18 1.4523(18) . ?
C8 C9 1.4147(18) . ?
C9 C10 1.3709(18) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.3705(18) . ?
C13 C23 1.5016(17) . ?
C14 C15 1.4120(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.4176(18) . ?
C16 C17 1.3690(18) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.5117(19) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?

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
N7 Cu1 N5 153.02(4) . . ?
N7 Cu1 N4 82.03(4) . . ?
N5 Cu1 N4 82.50(4) . . ?
N7 Cu1 N1 108.04(5) . . ?
N5 Cu1 N1 91.69(5) . . ?
N4 Cu1 N1 82.66(4) . . ?
N7 Cu1 Cl1 97.29(4) . . ?
N5 Cu1 Cl1 95.99(3) . . ?
N4 Cu1 Cl1 174.48(3) . . ?
N1 Cu1 Cl1 102.72(4) . . ?
C1 N1 C21 120.13(11) . . ?
C1 N1 Cu1 130.44(9) . . ?
C21 N1 Cu1 105.32(8) . . ?
N1 C1 N2 119.60(12) . . ?
N1 C1 N3 125.05(12) . . ?
N2 C1 N3 115.34(12) . . ?
C1 N2 C2 123.62(12) . . ?
C1 N2 C3 121.41(11) . . ?
C2 N2 C3 114.01(11) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 N3 C5 121.88(12) . . ?
C1 N3 C4 123.47(12) . . ?
C5 N3 C4 114.39(12) . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C23 N4 C22 111.88(10) . . ?
C23 N4 C20 109.36(10) . . ?
C22 N4 C20 112.13(9) . . ?
C23 N4 Cu1 108.24(8) . . ?
C22 N4 Cu1 108.60(8) . . ?
C20 N4 Cu1 106.41(8) . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 N5 C10 116.45(11) . . ?
C6 N5 Cu1 115.71(8) . . ?
C10 N5 Cu1 127.44(8) . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C8 N6 C12 120.92(11) . . ?
C8 N6 C11 120.32(11) . . ?
C12 N6 C11 118.47(11) . . ?
N5 C6 C7 123.74(11) . . ?
N5 C6 C22 115.90(11) . . ?
C7 C6 C22 120.28(11) . . ?
C13 N7 C17 115.97(11) . . ?
C13 N7 Cu1 115.36(8) . . ?
C17 N7 Cu1 127.81(9) . . ?
C6 C7 C8 119.89(11) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C15 N8 C19 122.45(12) . . ?
C15 N8 C18 120.47(11) . . ?
C19 N8 C18 117.05(11) . . ?
N6 C8 C7 121.40(11) . . ?
N6 C8 C9 122.39(12) . . ?
C7 C8 C9 116.20(11) . . ?
C10 C9 C8 119.47(12) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
N5 C10 C9 124.22(12) . . ?
N5 C10 H10 117.9 . . ?
C9 C10 H10 117.9 . . ?
N6 C11 H11A 109.5 . . ?
N6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N6 C12 H12A 109.5 . . ?
N6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N7 C13 C14 123.74(11) . . ?
N7 C13 C23 115.57(11) . . ?
C14 C13 C23 120.65(12) . . ?
C13 C14 C15 120.33(12) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
N8 C15 C14 120.99(12) . . ?
N8 C15 C16 123.05(11) . . ?
C14 C15 C16 115.93(12) . . ?
C17 C16 C15 119.49(11) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
N7 C17 C16 124.54(12) . . ?
N7 C17 H17 117.7 . . ?
C16 C17 H17 117.7 . . ?
N8 C18 H18A 109.5 . . ?
N8 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N8 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N8 C19 H19A 109.5 . . ?
N8 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N8 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N4 C20 C21 111.05(10) . . ?
N4 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
N4 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
N1 C21 C20 106.42(10) . . ?
N1 C21 H21A 110.4 . . ?
C20 C21 H21A 110.4 . . ?
N1 C21 H21B 110.4 . . ?
C20 C21 H21B 110.4 . . ?
H21A C21 H21B 108.6 . . ?
N4 C22 C6 112.05(10) . . ?
N4 C22 H22A 109.2 . . ?
C6 C22 H22A 109.2 . . ?
N4 C22 H22B 109.2 . . ?
C6 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
N4 C23 C13 109.90(11) . . ?
N4 C23 H23A 109.7 . . ?
C13 C23 H23A 109.7 . . ?
N4 C23 H23B 109.7 . . ?
C13 C23 H23B 109.7 . . ?
H23A C23 H23B 108.2 . . ?

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
C21 N1 C1 N2 -152.62(12) . . . . ?
Cu1 N1 C1 N2 53.74(17) . . . . ?
C21 N1 C1 N3 26.23(19) . . . . ?
Cu1 N1 C1 N3 -127.41(12) . . . . ?
N1 C1 N2 C2 -143.31(14) . . . . ?
N3 C1 N2 C2 37.73(18) . . . . ?
N1 C1 N2 C3 24.76(19) . . . . ?
N3 C1 N2 C3 -154.19(12) . . . . ?
N1 C1 N3 C5 29.2(2) . . . . ?
N2 C1 N3 C5 -151.92(13) . . . . ?
N1 C1 N3 C4 -144.68(14) . . . . ?
N2 C1 N3 C4 34.21(18) . . . . ?
C10 N5 C6 C7 -1.29(18) . . . . ?
Cu1 N5 C6 C7 -174.57(10) . . . . ?
C10 N5 C6 C22 -178.05(11) . . . . ?
Cu1 N5 C6 C22 8.67(13) . . . . ?
N5 C6 C7 C8 0.77(19) . . . . ?
C22 C6 C7 C8 177.39(11) . . . . ?
C12 N6 C8 C7 -178.96(12) . . . . ?
C11 N6 C8 C7 7.33(19) . . . . ?
C12 N6 C8 C9 1.17(19) . . . . ?
C11 N6 C8 C9 -172.54(12) . . . . ?
C6 C7 C8 N6 -179.45(12) . . . . ?
C6 C7 C8 C9 0.43(18) . . . . ?
N6 C8 C9 C10 178.84(12) . . . . ?
C7 C8 C9 C10 -1.03(18) . . . . ?
C6 N5 C10 C9 0.63(18) . . . . ?
Cu1 N5 C10 C9 173.00(10) . . . . ?
C8 C9 C10 N5 0.5(2) . . . . ?
C17 N7 C13 C14 -0.77(19) . . . . ?
Cu1 N7 C13 C14 169.46(10) . . . . ?
C17 N7 C13 C23 176.85(11) . . . . ?
Cu1 N7 C13 C23 -12.92(14) . . . . ?
N7 C13 C14 C15 0.8(2) . . . . ?
C23 C13 C14 C15 -176.75(12) . . . . ?
C19 N8 C15 C14 173.53(12) . . . . ?
C18 N8 C15 C14 -4.35(19) . . . . ?
C19 N8 C15 C16 -4.7(2) . . . . ?
C18 N8 C15 C16 177.46(13) . . . . ?
C13 C14 C15 N8 -178.44(12) . . . . ?
C13 C14 C15 C16 -0.13(18) . . . . ?
N8 C15 C16 C17 177.86(12) . . . . ?
C14 C15 C16 C17 -0.42(18) . . . . ?
C13 N7 C17 C16 0.18(18) . . . . ?
Cu1 N7 C17 C16 -168.63(10) . . . . ?
C15 C16 C17 N7 0.41(19) . . . . ?
C23 N4 C20 C21 -158.66(10) . . . . ?
C22 N4 C20 C21 76.64(13) . . . . ?
Cu1 N4 C20 C21 -41.97(11) . . . . ?
C1 N1 C21 C20 155.76(12) . . . . ?
Cu1 N1 C21 C20 -44.75(11) . . . . ?
N4 C20 C21 N1 60.47(13) . . . . ?
C23 N4 C22 C6 143.82(10) . . . . ?
C20 N4 C22 C6 -92.88(12) . . . . ?
Cu1 N4 C22 C6 24.41(12) . . . . ?
N5 C6 C22 N4 -22.66(15) . . . . ?
C7 C6 C22 N4 160.46(11) . . . . ?
C22 N4 C23 C13 -150.87(10) . . . . ?
C20 N4 C23 C13 84.28(12) . . . . ?
Cu1 N4 C23 C13 -31.25(12) . . . . ?
N7 C13 C23 N4 30.04(16) . . . . ?
C14 C13 C23 N4 -152.25(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H4B N6 0.98 2.59 3.457(2) 148.2 3_767 yes
C10 H10 Cl1 0.95 2.75 3.3284(14) 120.0 . yes
C16 H16 Cl2 0.95 2.77 3.6787(14) 160.3 . yes
C17 H17 Cl1 0.95 2.82 3.3879(14) 119.2 . yes
C19 H19B N6 0.98 2.53 3.491(2) 167.9 3_666 yes
C19 H19C Cl2 0.98 2.66 3.5689(18) 153.6 . yes
C22 H22B Cl1 0.99 2.82 3.7423(16) 155.1 1_655 yes
C23 H23B Cl1 0.99 2.73 3.6058(15) 147.2 3_666 yes

_refine_diff_density_max         0.455
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.071


####################################################################### 
# 
# 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_C3
_database_code_depnum_ccdc_archive 'CCDC 2289696'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2023-08-20 deposited with the CCDC.	2024-01-04 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         'C19 H28 Br Cu N6, C2 H3 N, Br'
_chemical_formula_sum            'C21 H31 Br2 Cu N7'
_chemical_formula_weight         604.89

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   14.006(3)
_cell_length_b                   14.715(3)
_cell_length_c                   12.068(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.33(3)
_cell_angle_gamma                90
_cell_volume                     2487.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    95548
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      35.25

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_F_000             1220
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.233
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    4.114
_shelx_estimated_absorpt_T_min   0.414
_shelx_estimated_absorpt_T_max   0.493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270. Afterwards scaling of
reflection intensities was performed within STOE LANA. J. Koziskova, F. Hahn,
J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136-140.
;
_exptl_absorpt_correction_T_min  0.3478
_exptl_absorpt_correction_T_max  0.5464

_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'

_diffrn_detector                 Pilatus200K
_diffrn_detector_type            'DECTRIS PILATUS 200K'
_diffrn_detector_area_resol_mean 5.81

_diffrn_source                   'Genix Mo'
_diffrn_source_type              ?
_diffrn_radiation_probe          x-ray
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'

_diffrn_ambient_temperature      100

_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 3718 frames, detector distance = 60 mm
;
_diffrn_reflns_number            49459
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.183
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4873
_reflns_number_gt                4374
_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       
;
X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)
;
_computing_cell_refinement       
;
X-Area Recipe 1.36.0.0 (STOE, 2020)
;
_computing_data_reduction        
;
X-Area Integrate 1.78.3.0 (STOE, 2020)
X-Area LANA 1.83.8.0 (STOE, 2020)
;

_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.90, Darmstadt 2020
;
_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)+(0.0582P)²+15.5395P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         4873
_refine_ls_number_parameters     285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1206
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.054
_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
Br1 Br 0.13751(4) 0.18703(3) 0.75045(4) 0.02475(14) Uani 1 1 d . . . . .
Cu1 Cu 0.19180(3) 0.32046(3) 0.65650(4) 0.01092(14) Uani 1 1 d . . . . .
N1 N 0.0696(2) 0.3863(2) 0.6470(3) 0.0133(7) Uani 1 1 d . . . . .
N2 N -0.0525(2) 0.2824(2) 0.6240(3) 0.0135(7) Uani 1 1 d . . . . .
Br2 Br 0.71371(3) 0.27699(3) 0.43618(4) 0.01729(13) Uani 1 1 d . . . . .
N3 N -0.0759(2) 0.4052(2) 0.7405(3) 0.0135(7) Uani 1 1 d . . . . .
N4 N 0.2458(2) 0.4341(3) 0.5754(3) 0.0140(7) Uani 1 1 d . . . . .
N5 N 0.3118(3) 0.2656(3) 0.5905(3) 0.0156(7) Uani 1 1 d . . . . .
N6 N 0.2483(2) 0.3984(2) 0.8012(3) 0.0133(7) Uani 1 1 d . . . . .
C1 C -0.0180(3) 0.3580(3) 0.6711(3) 0.0122(8) Uani 1 1 d . . . . .
C2 C -0.0148(3) 0.2483(3) 0.5193(4) 0.0180(9) Uani 1 1 d . . . . .
H2A H -0.067664 0.227854 0.472033 0.027 Uiso 1 1 calc R U . . .
H2B H 0.028445 0.197288 0.533952 0.027 Uiso 1 1 calc R U . . .
H2C H 0.020193 0.296982 0.481776 0.027 Uiso 1 1 calc R U . . .
C3 C -0.1160(3) 0.2194(3) 0.6807(4) 0.0180(9) Uani 1 1 d . . . . .
H3A H -0.125952 0.240091 0.756930 0.027 Uiso 1 1 calc R U . . .
H3B H -0.087217 0.158666 0.681643 0.027 Uiso 1 1 calc R U . . .
H3C H -0.177460 0.217011 0.641608 0.027 Uiso 1 1 calc R U . . .
C4 C -0.0368(3) 0.4535(3) 0.8364(4) 0.0170(9) Uani 1 1 d . . . . .
H4A H -0.041109 0.519199 0.823753 0.026 Uiso 1 1 calc R U . . .
H4B H 0.030266 0.436371 0.847109 0.026 Uiso 1 1 calc R U . . .
H4C H -0.073214 0.437433 0.902639 0.026 Uiso 1 1 calc R U . . .
C5 C -0.1802(3) 0.4086(3) 0.7290(4) 0.0156(8) Uani 1 1 d . . . . .
H5A H -0.209399 0.371548 0.787155 0.023 Uiso 1 1 calc R U . . .
H5B H -0.198881 0.384918 0.656189 0.023 Uiso 1 1 calc R U . . .
H5C H -0.201886 0.471648 0.736103 0.023 Uiso 1 1 calc R U . . .
C6 C 0.3471(3) 0.3137(3) 0.5052(4) 0.0186(9) Uani 1 1 d . . . . .
C7 C 0.4279(3) 0.2846(4) 0.4479(4) 0.0248(11) Uani 1 1 d . . . . .
H7 H 0.452480 0.319616 0.388378 0.030 Uiso 1 1 calc R U . . .
C8 C 0.4715(3) 0.2043(4) 0.4788(4) 0.0266(11) Uani 1 1 d . . . . .
H8 H 0.525559 0.182535 0.439625 0.032 Uiso 1 1 calc R U . . .
C9 C 0.4356(3) 0.1561(3) 0.5675(4) 0.0230(10) Uani 1 1 d . . . . .
H9 H 0.465033 0.101187 0.590883 0.028 Uiso 1 1 calc R U . . .
C10 C 0.3563(3) 0.1889(3) 0.6216(4) 0.0183(9) Uani 1 1 d . . . . .
H10 H 0.332230 0.156043 0.683160 0.022 Uiso 1 1 calc R U . . .
C11 C 0.2890(3) 0.4763(3) 0.7690(4) 0.0142(8) Uani 1 1 d . . . . .
C12 C 0.3051(3) 0.5482(3) 0.8406(4) 0.0196(9) Uani 1 1 d . . . . .
H12 H 0.334615 0.602441 0.815280 0.024 Uiso 1 1 calc R U . . .
C13 C 0.2770(4) 0.5393(3) 0.9504(4) 0.0239(10) Uani 1 1 d . . . . .
H13 H 0.286887 0.587621 1.001401 0.029 Uiso 1 1 calc R U . . .
C14 C 0.2349(3) 0.4597(3) 0.9843(4) 0.0202(9) Uani 1 1 d . . . . .
H14 H 0.215261 0.452214 1.058932 0.024 Uiso 1 1 calc R U . . .
C15 C 0.2215(3) 0.3903(3) 0.9074(3) 0.0152(8) Uani 1 1 d . . . . .
H15 H 0.192468 0.335340 0.930920 0.018 Uiso 1 1 calc R U . . .
C16 C 0.1631(3) 0.4947(3) 0.5496(4) 0.0193(9) Uani 1 1 d . . . . .
H16A H 0.135555 0.478560 0.476491 0.023 Uiso 1 1 calc R U . . .
H16B H 0.184712 0.558750 0.546575 0.023 Uiso 1 1 calc R U . . .
C17 C 0.0883(3) 0.4839(3) 0.6387(4) 0.0154(9) Uani 1 1 d . . . . .
H17A H 0.112211 0.507887 0.710272 0.018 Uiso 1 1 calc R U . . .
H17B H 0.029303 0.516993 0.618129 0.018 Uiso 1 1 calc R U . . .
C18 C 0.2933(3) 0.3988(3) 0.4756(4) 0.0200(9) Uani 1 1 d . . . . .
H18A H 0.337915 0.444906 0.446182 0.024 Uiso 1 1 calc R U . . .
H18B H 0.245104 0.385229 0.417555 0.024 Uiso 1 1 calc R U . . .
C19 C 0.3175(3) 0.4796(3) 0.6481(3) 0.0152(9) Uani 1 1 d . . . . .
H19A H 0.324448 0.543756 0.624910 0.018 Uiso 1 1 calc R U . . .
H19B H 0.380162 0.449436 0.639171 0.018 Uiso 1 1 calc R U . . .
N13 N 0.4301(4) 0.5007(4) 0.2659(4) 0.0395(12) Uani 1 1 d . . . . .
C39 C 0.4259(3) 0.5764(4) 0.2798(4) 0.0246(11) Uani 1 1 d . . . . .
C40 C 0.4209(4) 0.6740(4) 0.2998(4) 0.0250(11) Uani 1 1 d . . . . .
H40A H 0.381939 0.702728 0.241843 0.037 Uiso 1 1 calc R U . . .
H40B H 0.485420 0.699775 0.298653 0.037 Uiso 1 1 calc R U . . .
H40C H 0.391986 0.685213 0.372268 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Cu1 2.3935(8) . ?
Cu1 N1 1.970(4) . ?
Cu1 N5 2.031(4) . ?
Cu1 N4 2.082(4) . ?
Cu1 N6 2.231(4) . ?
N1 C1 1.328(5) . ?
N1 C17 1.463(5) . ?
N2 C1 1.339(6) . ?
N2 C3 1.458(5) . ?
N2 C2 1.460(5) . ?
N3 C1 1.360(5) . ?
N3 C4 1.462(5) . ?
N3 C5 1.467(5) . ?
N4 C18 1.474(6) . ?
N4 C19 1.489(5) . ?
N4 C16 1.494(6) . ?
N5 C10 1.342(6) . ?
N5 C6 1.346(6) . ?
N6 C11 1.339(6) . ?
N6 C15 1.342(6) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.396(7) . ?
C6 C18 1.503(7) . ?
C7 C8 1.381(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(6) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.384(6) . ?
C11 C19 1.516(6) . ?
C12 C13 1.391(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.375(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(6) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.514(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
N13 C39 1.128(7) . ?
C39 C40 1.458(8) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?

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
N1 Cu1 N5 153.29(15) . . ?
N1 Cu1 N4 84.02(14) . . ?
N5 Cu1 N4 80.25(15) . . ?
N1 Cu1 N6 95.55(14) . . ?
N5 Cu1 N6 102.77(14) . . ?
N4 Cu1 N6 80.05(13) . . ?
N1 Cu1 Br1 98.78(10) . . ?
N5 Cu1 Br1 97.23(11) . . ?
N4 Cu1 Br1 177.19(10) . . ?
N6 Cu1 Br1 99.39(9) . . ?
C1 N1 C17 119.3(4) . . ?
C1 N1 Cu1 129.5(3) . . ?
C17 N1 Cu1 109.3(3) . . ?
C1 N2 C3 123.3(4) . . ?
C1 N2 C2 121.4(4) . . ?
C3 N2 C2 114.3(3) . . ?
C1 N3 C4 120.9(3) . . ?
C1 N3 C5 123.8(4) . . ?
C4 N3 C5 115.2(3) . . ?
C18 N4 C19 109.5(3) . . ?
C18 N4 C16 113.2(3) . . ?
C19 N4 C16 111.9(3) . . ?
C18 N4 Cu1 105.6(3) . . ?
C19 N4 Cu1 109.2(2) . . ?
C16 N4 Cu1 107.1(2) . . ?
C10 N5 C6 118.9(4) . . ?
C10 N5 Cu1 127.5(3) . . ?
C6 N5 Cu1 113.6(3) . . ?
C11 N6 C15 118.4(4) . . ?
C11 N6 Cu1 111.2(3) . . ?
C15 N6 Cu1 127.0(3) . . ?
N1 C1 N2 119.9(4) . . ?
N1 C1 N3 122.0(4) . . ?
N2 C1 N3 118.1(4) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N5 C6 C7 121.3(5) . . ?
N5 C6 C18 115.7(4) . . ?
C7 C6 C18 123.0(4) . . ?
C8 C7 C6 119.2(5) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 119.0(4) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 119.0(5) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
N5 C10 C9 122.4(4) . . ?
N5 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
N6 C11 C12 122.8(4) . . ?
N6 C11 C19 115.0(4) . . ?
C12 C11 C19 122.3(4) . . ?
C11 C12 C13 118.5(4) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C14 C13 C12 119.2(4) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 118.9(4) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
N6 C15 C14 122.3(4) . . ?
N6 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
N4 C16 C17 109.1(3) . . ?
N4 C16 H16A 109.9 . . ?
C17 C16 H16A 109.9 . . ?
N4 C16 H16B 109.9 . . ?
C17 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
N1 C17 C16 106.1(4) . . ?
N1 C17 H17A 110.5 . . ?
C16 C17 H17A 110.5 . . ?
N1 C17 H17B 110.5 . . ?
C16 C17 H17B 110.5 . . ?
H17A C17 H17B 108.7 . . ?
N4 C18 C6 109.1(4) . . ?
N4 C18 H18A 109.9 . . ?
C6 C18 H18A 109.9 . . ?
N4 C18 H18B 109.9 . . ?
C6 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
N4 C19 C11 111.9(3) . . ?
N4 C19 H19A 109.2 . . ?
C11 C19 H19A 109.2 . . ?
N4 C19 H19B 109.2 . . ?
C11 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
N13 C39 C40 179.0(6) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

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
C17 N1 C1 N2 143.4(4) . . . . ?
Cu1 N1 C1 N2 -54.3(5) . . . . ?
C17 N1 C1 N3 -34.6(6) . . . . ?
Cu1 N1 C1 N3 127.6(4) . . . . ?
C3 N2 C1 N1 145.1(4) . . . . ?
C2 N2 C1 N1 -23.1(6) . . . . ?
C3 N2 C1 N3 -36.8(6) . . . . ?
C2 N2 C1 N3 155.0(4) . . . . ?
C4 N3 C1 N1 -35.4(6) . . . . ?
C5 N3 C1 N1 147.4(4) . . . . ?
C4 N3 C1 N2 146.5(4) . . . . ?
C5 N3 C1 N2 -30.7(6) . . . . ?
C10 N5 C6 C7 0.9(6) . . . . ?
Cu1 N5 C6 C7 -178.2(3) . . . . ?
C10 N5 C6 C18 -179.9(4) . . . . ?
Cu1 N5 C6 C18 0.9(5) . . . . ?
N5 C6 C7 C8 0.8(7) . . . . ?
C18 C6 C7 C8 -178.3(4) . . . . ?
C6 C7 C8 C9 -1.7(7) . . . . ?
C7 C8 C9 C10 0.9(7) . . . . ?
C6 N5 C10 C9 -1.8(6) . . . . ?
Cu1 N5 C10 C9 177.3(3) . . . . ?
C8 C9 C10 N5 0.8(7) . . . . ?
C15 N6 C11 C12 0.5(6) . . . . ?
Cu1 N6 C11 C12 161.2(3) . . . . ?
C15 N6 C11 C19 179.7(4) . . . . ?
Cu1 N6 C11 C19 -19.6(4) . . . . ?
N6 C11 C12 C13 -0.5(7) . . . . ?
C19 C11 C12 C13 -179.7(4) . . . . ?
C11 C12 C13 C14 0.3(7) . . . . ?
C12 C13 C14 C15 0.0(7) . . . . ?
C11 N6 C15 C14 -0.2(6) . . . . ?
Cu1 N6 C15 C14 -157.5(3) . . . . ?
C13 C14 C15 N6 -0.1(7) . . . . ?
C18 N4 C16 C17 147.4(4) . . . . ?
C19 N4 C16 C17 -88.3(4) . . . . ?
Cu1 N4 C16 C17 31.4(4) . . . . ?
C1 N1 C17 C16 -146.1(4) . . . . ?
Cu1 N1 C17 C16 48.3(4) . . . . ?
N4 C16 C17 N1 -52.5(4) . . . . ?
C19 N4 C18 C6 76.3(4) . . . . ?
C16 N4 C18 C6 -158.0(3) . . . . ?
Cu1 N4 C18 C6 -41.2(4) . . . . ?
N5 C6 C18 N4 28.1(5) . . . . ?
C7 C6 C18 N4 -152.8(4) . . . . ?
C18 N4 C19 C11 -152.2(4) . . . . ?
C16 N4 C19 C11 81.4(4) . . . . ?
Cu1 N4 C19 C11 -37.0(4) . . . . ?
N6 C11 C19 N4 38.6(5) . . . . ?
C12 C11 C19 N4 -142.2(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C10 H10 Br1 0.95 2.89 3.444(5) 118.6 . yes
C16 H16B Br2 0.99 2.81 3.780(5) 165.9 3_666 yes
C18 H18B Br1 0.99 2.73 3.697(5) 166.7 4_565 yes
C19 H19A Br2 0.99 2.79 3.749(4) 163.3 3_666 yes
C40 H40A Br2 0.98 2.75 3.728(5) 174.1 2_655 yes
C40 H40C Br2 0.98 2.81 3.781(5) 172.2 3_666 yes

_refine_diff_density_max         1.069
_refine_diff_density_min         -2.027
_refine_diff_density_rms         0.137


####################################################################### 
# 
# 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_C4
_database_code_depnum_ccdc_archive 'CCDC 2289697'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2023-08-20 deposited with the CCDC.	2024-01-04 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         'C21 H48 Br Cu N10, Br'
_chemical_formula_sum            'C21 H48 Br2 Cu N10'
_chemical_formula_weight         664.05

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   17.874(4)
_cell_length_b                   18.131(4)
_cell_length_c                   17.985(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.20(3)
_cell_angle_gamma                90
_cell_volume                     5827(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    77115
_cell_measurement_theta_min      1.60
_cell_measurement_theta_max      33.68

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_F_000             2744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    3.521
_shelx_estimated_absorpt_T_min   0.461
_shelx_estimated_absorpt_T_max   0.498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270. Afterwards scaling of
reflection intensities was performed within STOE LANA. J. Koziskova, F. Hahn,
J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136-140.
;
_exptl_absorpt_correction_T_min  0.1847
_exptl_absorpt_correction_T_max  0.2645

_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'

_diffrn_detector                 Pilatus200K
_diffrn_detector_type            'DECTRIS PILATUS 200K'
_diffrn_detector_area_resol_mean 5.81

_diffrn_source                   'Genix Mo'
_diffrn_source_type              ?
_diffrn_radiation_probe          x-ray
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'

_diffrn_ambient_temperature      100

_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 2399 frames, detector distance = 60 mm
;

_diffrn_reflns_number            108428
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_av_R_equivalents  0.1345
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.590
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             12711
_reflns_number_gt                9194
_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       
;
X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)
;
_computing_cell_refinement       
;
X-Area Recipe 1.36.0.0 (STOE, 2020)
;
_computing_data_reduction        
;
X-Area Integrate 1.78.3.0 (STOE, 2020)
X-Area LANA 1.83.8.0 (STOE, 2020)
;

_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.90, Darmstadt 2020
;

_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)+(0.0581P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         12711
_refine_ls_number_parameters     637
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1135
_refine_ls_wR_factor_gt          0.0996
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.002
_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 1.02445(2) 0.72416(2) 0.49210(2) 0.01290(11) Uani 1 1 d . . . . .
N1 N 0.94297(16) 0.65336(16) 0.45181(16) 0.0136(6) Uani 1 1 d . . . . .
C1 C 0.8735(2) 0.64201(19) 0.4706(2) 0.0135(8) Uani 1 1 d . . . . .
Cu2 Cu 0.52024(2) 0.22177(2) 0.45899(2) 0.01293(11) Uani 1 1 d . . . . .
N2 N 0.85461(16) 0.63862(16) 0.54321(17) 0.0140(6) Uani 1 1 d . . . . .
C2 C 0.90979(19) 0.6186(2) 0.6000(2) 0.0160(8) Uani 1 1 d . . . . .
H2A H 0.886627 0.586431 0.636746 0.024 Uiso 1 1 calc R U . . .
H2B H 0.928667 0.663282 0.624580 0.024 Uiso 1 1 calc R U . . .
H2C H 0.951352 0.592503 0.576908 0.024 Uiso 1 1 calc R U . . .
Br3 Br 0.74519(2) 0.00326(2) 0.28576(2) 0.02575(11) Uani 1 1 d . . . . .
N3 N 0.81668(17) 0.62978(17) 0.42024(17) 0.0187(7) Uani 1 1 d . . . . .
C3 C 0.7854(2) 0.6689(2) 0.5711(2) 0.0222(9) Uani 1 1 d . . . . .
H3A H 0.760697 0.631990 0.601789 0.033 Uiso 1 1 calc R U . . .
H3B H 0.752372 0.682471 0.529094 0.033 Uiso 1 1 calc R U . . .
H3C H 0.796571 0.712848 0.601088 0.033 Uiso 1 1 calc R U . . .
Br4 Br 0.74000(2) -0.01920(2) 0.81910(2) 0.01965(10) Uani 1 1 d . . . . .
N4 N 1.09645(16) 0.69569(16) 0.57869(17) 0.0136(6) Uani 1 1 d . . . . .
C4 C 0.7556(2) 0.5793(2) 0.4338(2) 0.0240(9) Uani 1 1 d . . . . .
H4A H 0.749422 0.545794 0.391432 0.036 Uiso 1 1 calc R U . . .
H4B H 0.709335 0.607387 0.440350 0.036 Uiso 1 1 calc R U . . .
H4C H 0.766745 0.550713 0.478953 0.036 Uiso 1 1 calc R U . . .
N5 N 1.12246(17) 0.68050(17) 0.70635(17) 0.0172(7) Uani 1 1 d . . . . .
C5 C 0.8132(2) 0.6641(2) 0.3475(2) 0.0221(9) Uani 1 1 d . . . . .
H5A H 0.765526 0.690368 0.341249 0.033 Uiso 1 1 calc R U . . .
H5B H 0.816922 0.626082 0.309011 0.033 Uiso 1 1 calc R U . . .
H5C H 0.854645 0.699041 0.343006 0.033 Uiso 1 1 calc R U . . .
N6 N 1.11983(17) 0.79681(17) 0.65406(17) 0.0163(7) Uani 1 1 d . . . . .
C6 C 1.11141(19) 0.7234(2) 0.6450(2) 0.0145(8) Uani 1 1 d . . . . .
N7 N 1.06154(17) 0.80110(16) 0.41071(17) 0.0151(7) Uani 1 1 d . . . . .
C7 C 1.0784(2) 0.6154(2) 0.7209(2) 0.0250(9) Uani 1 1 d . . . . .
H7A H 1.110882 0.571833 0.720846 0.038 Uiso 1 1 calc R U . . .
H7B H 1.039395 0.610112 0.682166 0.038 Uiso 1 1 calc R U . . .
H7C H 1.055139 0.620093 0.769510 0.038 Uiso 1 1 calc R U . . .
N8 N 0.96863(17) 0.88660(17) 0.38164(18) 0.0199(7) Uani 1 1 d . . . . .
C8 C 1.1774(2) 0.7000(2) 0.7643(2) 0.0267(10) Uani 1 1 d . . . . .
H8A H 1.207861 0.656618 0.776886 0.040 Uiso 1 1 calc R U . . .
H8B H 1.151385 0.716822 0.808646 0.040 Uiso 1 1 calc R U . . .
H8C H 1.209716 0.739478 0.746328 0.040 Uiso 1 1 calc R U . . .
N9 N 1.09242(17) 0.92283(18) 0.37705(18) 0.0229(8) Uani 1 1 d . . . . .
C9 C 1.0931(2) 0.8364(2) 0.7185(2) 0.0209(9) Uani 1 1 d . . . . .
H9A H 1.133763 0.866413 0.739884 0.031 Uiso 1 1 calc R U . . .
H9B H 1.076107 0.801032 0.755747 0.031 Uiso 1 1 calc R U . . .
H9C H 1.051353 0.868506 0.703408 0.031 Uiso 1 1 calc R U . . .
N10 N 1.09413(16) 0.65240(17) 0.43216(17) 0.0165(7) Uani 1 1 d . . . . .
C10 C 1.1392(2) 0.8443(2) 0.5922(2) 0.0196(8) Uani 1 1 d . . . . .
H10A H 1.169533 0.885675 0.610695 0.029 Uiso 1 1 calc R U . . .
H10B H 1.093378 0.863107 0.568189 0.029 Uiso 1 1 calc R U . . .
H10C H 1.167830 0.815958 0.556116 0.029 Uiso 1 1 calc R U . . .
Br1 Br 0.94484(2) 0.80775(2) 0.56218(2) 0.01803(10) Uani 1 1 d . . . . .
N11 N 0.43598(16) 0.15397(16) 0.41346(16) 0.0123(6) Uani 1 1 d . . . . .
C11 C 1.0422(2) 0.8681(2) 0.3920(2) 0.0192(8) Uani 1 1 d . . . . .
N12 N 0.34907(16) 0.12760(16) 0.50404(16) 0.0144(7) Uani 1 1 d . . . . .
C12 C 0.9132(2) 0.8305(2) 0.3642(2) 0.0218(9) Uani 1 1 d . . . . .
H12A H 0.872820 0.852082 0.333607 0.033 Uiso 1 1 calc R U . . .
H12B H 0.892642 0.811248 0.410409 0.033 Uiso 1 1 calc R U . . .
H12C H 0.936696 0.790247 0.336807 0.033 Uiso 1 1 calc R U . . .
N13 N 0.30880(16) 0.13696(16) 0.38129(17) 0.0152(7) Uani 1 1 d . . . . .
C13 C 0.9380(3) 0.9553(2) 0.4091(3) 0.0320(11) Uani 1 1 d . . . . .
H13A H 0.906032 0.977731 0.370397 0.048 Uiso 1 1 calc R U . . .
H13B H 0.979037 0.989096 0.422164 0.048 Uiso 1 1 calc R U . . .
H13C H 0.908419 0.945461 0.453234 0.048 Uiso 1 1 calc R U . . .
N14 N 0.59434(16) 0.17749(16) 0.53944(16) 0.0146(7) Uani 1 1 d . . . . .
C14 C 1.0790(2) 0.9799(2) 0.3216(2) 0.0324(11) Uani 1 1 d . . . . .
H14A H 1.122237 0.983337 0.289107 0.049 Uiso 1 1 calc R U . . .
H14B H 1.071637 1.027380 0.346519 0.049 Uiso 1 1 calc R U . . .
H14C H 1.034233 0.967626 0.291816 0.049 Uiso 1 1 calc R U . . .
N15 N 0.62944(17) 0.14319(17) 0.66203(17) 0.0165(7) Uani 1 1 d . . . . .
C15 C 1.1604(2) 0.9319(2) 0.4219(2) 0.0257(10) Uani 1 1 d . . . . .
H15A H 1.160074 0.980496 0.445765 0.039 Uiso 1 1 calc R U . . .
H15B H 1.203987 0.928003 0.389995 0.039 Uiso 1 1 calc R U . . .
H15C H 1.162856 0.893414 0.460070 0.039 Uiso 1 1 calc R U . . .
N16 N 0.61819(16) 0.26608(16) 0.63032(17) 0.0153(7) Uani 1 1 d . . . . .
C16 C 0.9702(2) 0.6174(2) 0.3848(2) 0.0181(8) Uani 1 1 d . . . . .
H16A H 0.971982 0.652922 0.343092 0.022 Uiso 1 1 calc R U . . .
H16B H 0.937022 0.575928 0.370116 0.022 Uiso 1 1 calc R U . . .
N17 N 0.55642(17) 0.30840(16) 0.39013(17) 0.0152(7) Uani 1 1 d . . . . .
C17 C 1.0479(2) 0.5895(2) 0.4044(2) 0.0197(8) Uani 1 1 d . . . . .
H17A H 1.045049 0.550944 0.443213 0.024 Uiso 1 1 calc R U . . .
H17B H 1.070868 0.567618 0.359942 0.024 Uiso 1 1 calc R U . . .
N18 N 0.46255(17) 0.39694(17) 0.37686(17) 0.0174(7) Uani 1 1 d . . . . .
C18 C 1.1248(2) 0.62167(19) 0.5614(2) 0.0165(8) Uani 1 1 d . . . . .
H18A H 1.083960 0.584858 0.563479 0.020 Uiso 1 1 calc R U . . .
H18B H 1.164791 0.607238 0.597443 0.020 Uiso 1 1 calc R U . . .
N19 N 0.58562(17) 0.43514(17) 0.38247(18) 0.0208(7) Uani 1 1 d . . . . .
C19 C 1.1551(2) 0.6262(2) 0.4840(2) 0.0200(9) Uani 1 1 d . . . . .
H19A H 1.197795 0.660938 0.483127 0.024 Uiso 1 1 calc R U . . .
H19B H 1.172902 0.577102 0.468103 0.024 Uiso 1 1 calc R U . . .
N20 N 0.58735(16) 0.15936(16) 0.38690(16) 0.0140(6) Uani 1 1 d . . . . .
C20 C 1.1350(2) 0.7743(2) 0.3883(2) 0.0214(9) Uani 1 1 d . . . . .
H20A H 1.172025 0.780028 0.429566 0.026 Uiso 1 1 calc R U . . .
H20B H 1.152612 0.802533 0.344888 0.026 Uiso 1 1 calc R U . . .
C21 C 1.1258(2) 0.6931(2) 0.3681(2) 0.0199(9) Uani 1 1 d . . . . .
H21A H 1.091950 0.688252 0.324131 0.024 Uiso 1 1 calc R U . . .
H21B H 1.174959 0.671929 0.355534 0.024 Uiso 1 1 calc R U . . .
C22 C 0.3671(2) 0.14127(18) 0.4317(2) 0.0141(8) Uani 1 1 d . . . . .
C23 C 0.4061(2) 0.1016(2) 0.5567(2) 0.0181(8) Uani 1 1 d . . . . .
H23A H 0.382911 0.070137 0.594009 0.027 Uiso 1 1 calc R U . . .
H23B H 0.430045 0.143944 0.581286 0.027 Uiso 1 1 calc R U . . .
H23C H 0.443835 0.073215 0.530138 0.027 Uiso 1 1 calc R U . . .
C24 C 0.2817(2) 0.1565(2) 0.5374(2) 0.0207(9) Uani 1 1 d . . . . .
H24A H 0.258869 0.118112 0.567879 0.031 Uiso 1 1 calc R U . . .
H24B H 0.246235 0.171828 0.498135 0.031 Uiso 1 1 calc R U . . .
H24C H 0.294683 0.199010 0.568783 0.031 Uiso 1 1 calc R U . . .
C25 C 0.2473(2) 0.0849(2) 0.3899(2) 0.0188(8) Uani 1 1 d . . . . .
H25A H 0.239644 0.057205 0.343619 0.028 Uiso 1 1 calc R U . . .
H25B H 0.201511 0.111986 0.401407 0.028 Uiso 1 1 calc R U . . .
H25C H 0.259468 0.050673 0.430556 0.028 Uiso 1 1 calc R U . . .
C26 C 0.3049(2) 0.1805(2) 0.3136(2) 0.0179(8) Uani 1 1 d . . . . .
H26A H 0.256871 0.206582 0.310784 0.027 Uiso 1 1 calc R U . . .
H26B H 0.309179 0.147898 0.270449 0.027 Uiso 1 1 calc R U . . .
H26C H 0.345861 0.216373 0.313920 0.027 Uiso 1 1 calc R U . . .
C27 C 0.6123(2) 0.1943(2) 0.6082(2) 0.0160(8) Uani 1 1 d . . . . .
C28 C 0.6362(2) 0.3235(2) 0.5774(2) 0.0185(8) Uani 1 1 d . . . . .
H28A H 0.666864 0.361352 0.602151 0.028 Uiso 1 1 calc R U . . .
H28B H 0.589822 0.345867 0.557951 0.028 Uiso 1 1 calc R U . . .
H28C H 0.663958 0.302061 0.536238 0.028 Uiso 1 1 calc R U . . .
C29 C 0.5901(2) 0.2929(2) 0.7009(2) 0.0249(9) Uani 1 1 d . . . . .
H29A H 0.552583 0.331393 0.691490 0.037 Uiso 1 1 calc R U . . .
H29B H 0.631635 0.313399 0.730806 0.037 Uiso 1 1 calc R U . . .
H29C H 0.567276 0.252045 0.727929 0.037 Uiso 1 1 calc R U . . .
C30 C 0.6865(2) 0.1578(2) 0.7198(2) 0.0230(9) Uani 1 1 d . . . . .
H30A H 0.715983 0.112979 0.728963 0.034 Uiso 1 1 calc R U . . .
H30B H 0.662207 0.172697 0.765763 0.034 Uiso 1 1 calc R U . . .
H30C H 0.719579 0.197407 0.703341 0.034 Uiso 1 1 calc R U . . .
C31 C 0.5942(2) 0.0714(2) 0.6649(2) 0.0240(9) Uani 1 1 d . . . . .
H31A H 0.579695 0.060801 0.716074 0.036 Uiso 1 1 calc R U . . .
H31B H 0.629443 0.033676 0.648362 0.036 Uiso 1 1 calc R U . . .
H31C H 0.549605 0.071011 0.632272 0.036 Uiso 1 1 calc R U . . .
C32 C 0.5360(2) 0.3781(2) 0.3846(2) 0.0164(8) Uani 1 1 d . . . . .
C33 C 0.4087(2) 0.3433(2) 0.3486(2) 0.0205(9) Uani 1 1 d . . . . .
H33A H 0.366230 0.369112 0.325014 0.031 Uiso 1 1 calc R U . . .
H33B H 0.390890 0.313043 0.389732 0.031 Uiso 1 1 calc R U . . .
H33C H 0.432581 0.311615 0.311864 0.031 Uiso 1 1 calc R U . . .
C34 C 0.4298(2) 0.4582(2) 0.4173(2) 0.0245(9) Uani 1 1 d . . . . .
H34A H 0.395755 0.485692 0.384065 0.037 Uiso 1 1 calc R U . . .
H34B H 0.469628 0.491042 0.435613 0.037 Uiso 1 1 calc R U . . .
H34C H 0.401865 0.439089 0.459515 0.037 Uiso 1 1 calc R U . . .
C35 C 0.5733(2) 0.5032(2) 0.3413(2) 0.0274(10) Uani 1 1 d . . . . .
H35A H 0.614307 0.510686 0.306730 0.041 Uiso 1 1 calc R U . . .
H35B H 0.571655 0.544750 0.376142 0.041 Uiso 1 1 calc R U . . .
H35C H 0.525799 0.500189 0.313351 0.041 Uiso 1 1 calc R U . . .
C36 C 0.6567(2) 0.4319(2) 0.4232(2) 0.0233(9) Uani 1 1 d . . . . .
H36A H 0.661480 0.475159 0.455707 0.035 Uiso 1 1 calc R U . . .
H36B H 0.697782 0.431524 0.388043 0.035 Uiso 1 1 calc R U . . .
H36C H 0.658619 0.386968 0.453451 0.035 Uiso 1 1 calc R U . . .
C37 C 0.4619(2) 0.1307(2) 0.3406(2) 0.0170(8) Uani 1 1 d . . . . .
H37A H 0.462176 0.173044 0.305833 0.020 Uiso 1 1 calc R U . . .
H37B H 0.428569 0.092029 0.319521 0.020 Uiso 1 1 calc R U . . .
C38 C 0.5401(2) 0.1009(2) 0.3523(2) 0.0177(8) Uani 1 1 d . . . . .
H38A H 0.539085 0.057081 0.385038 0.021 Uiso 1 1 calc R U . . .
H38B H 0.561037 0.086013 0.304008 0.021 Uiso 1 1 calc R U . . .
C39 C 0.6242(2) 0.1090(2) 0.5084(2) 0.0163(8) Uani 1 1 d . . . . .
H39A H 0.584905 0.070536 0.506219 0.020 Uiso 1 1 calc R U . . .
H39B H 0.666509 0.090670 0.539598 0.020 Uiso 1 1 calc R U . . .
C40 C 0.6503(2) 0.1268(2) 0.4311(2) 0.0185(8) Uani 1 1 d . . . . .
H40A H 0.692444 0.162140 0.434067 0.022 Uiso 1 1 calc R U . . .
H40B H 0.667964 0.081303 0.406652 0.022 Uiso 1 1 calc R U . . .
C41 C 0.6283(2) 0.2860(2) 0.3603(2) 0.0183(8) Uani 1 1 d . . . . .
H41A H 0.667336 0.285385 0.400222 0.022 Uiso 1 1 calc R U . . .
H41B H 0.643932 0.320596 0.321014 0.022 Uiso 1 1 calc R U . . .
C42 C 0.6170(2) 0.2095(2) 0.3286(2) 0.0186(8) Uani 1 1 d . . . . .
H42A H 0.581334 0.211587 0.285838 0.022 Uiso 1 1 calc R U . . .
H42B H 0.665215 0.190169 0.310775 0.022 Uiso 1 1 calc R U . . .
Br2 Br 0.44208(2) 0.29327(2) 0.54207(2) 0.01719(9) 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 N1 2.061(3) . ?
Cu1 N4 2.065(3) . ?
Cu1 N10 2.112(3) . ?
Cu1 N7 2.138(3) . ?
Cu1 Br1 2.4466(7) . ?
N1 C1 1.310(4) . ?
N1 C16 1.463(4) . ?
C1 N2 1.357(4) . ?
C1 N3 1.365(4) . ?
Cu2 N11 2.097(3) . ?
Cu2 N14 2.100(3) . ?
Cu2 N17 2.110(3) . ?
Cu2 N20 2.113(3) . ?
Cu2 Br2 2.4398(8) . ?
N2 C2 1.451(4) . ?
N2 C3 1.452(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N3 C4 1.449(4) . ?
N3 C5 1.449(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
N4 C6 1.317(5) . ?
N4 C18 1.470(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N5 C6 1.360(5) . ?
N5 C7 1.446(5) . ?
N5 C8 1.460(5) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
N6 C6 1.349(5) . ?
N6 C9 1.453(4) . ?
N6 C10 1.454(5) . ?
N7 C11 1.306(5) . ?
N7 C20 1.465(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
N8 C11 1.367(5) . ?
N8 C12 1.450(4) . ?
N8 C13 1.451(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N9 C11 1.367(5) . ?
N9 C15 1.453(5) . ?
N9 C14 1.454(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
N10 C17 1.489(4) . ?
N10 C21 1.490(5) . ?
N10 C19 1.496(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
N11 C22 1.302(4) . ?
N11 C37 1.462(4) . ?
N12 C22 1.369(5) . ?
N12 C24 1.454(4) . ?
N12 C23 1.455(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N13 C22 1.369(4) . ?
N13 C26 1.451(4) . ?
N13 C25 1.459(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N14 C27 1.308(5) . ?
N14 C39 1.467(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N15 C27 1.370(5) . ?
N15 C31 1.448(5) . ?
N15 C30 1.465(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N16 C27 1.364(5) . ?
N16 C28 1.452(5) . ?
N16 C29 1.459(5) . ?
C16 C17 1.512(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
N17 C32 1.319(5) . ?
N17 C41 1.460(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
N18 C32 1.362(5) . ?
N18 C33 1.453(4) . ?
N18 C34 1.458(5) . ?
C18 C19 1.508(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N19 C32 1.363(4) . ?
N19 C35 1.454(5) . ?
N19 C36 1.454(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
N20 C38 1.483(4) . ?
N20 C40 1.486(4) . ?
N20 C42 1.493(5) . ?
C20 C21 1.523(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C38 1.510(5) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.509(5) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C42 1.512(5) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?

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
N1 Cu1 N4 122.28(12) . . ?
N1 Cu1 N10 81.77(12) . . ?
N4 Cu1 N10 82.30(12) . . ?
N1 Cu1 N7 113.12(12) . . ?
N4 Cu1 N7 118.83(12) . . ?
N10 Cu1 N7 81.82(12) . . ?
N1 Cu1 Br1 98.78(9) . . ?
N4 Cu1 Br1 97.26(9) . . ?
N10 Cu1 Br1 179.43(9) . . ?
N7 Cu1 Br1 98.08(9) . . ?
C1 N1 C16 118.5(3) . . ?
C1 N1 Cu1 132.3(2) . . ?
C16 N1 Cu1 108.8(2) . . ?
N1 C1 N2 120.8(3) . . ?
N1 C1 N3 123.4(3) . . ?
N2 C1 N3 115.8(3) . . ?
N11 Cu2 N14 118.82(11) . . ?
N11 Cu2 N17 115.70(11) . . ?
N14 Cu2 N17 119.49(12) . . ?
N11 Cu2 N20 81.88(11) . . ?
N14 Cu2 N20 81.96(12) . . ?
N17 Cu2 N20 81.59(12) . . ?
N11 Cu2 Br2 97.75(8) . . ?
N14 Cu2 Br2 98.18(8) . . ?
N17 Cu2 Br2 98.65(9) . . ?
N20 Cu2 Br2 179.62(9) . . ?
C1 N2 C2 120.6(3) . . ?
C1 N2 C3 123.1(3) . . ?
C2 N2 C3 115.0(3) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 N3 C4 122.9(3) . . ?
C1 N3 C5 123.2(3) . . ?
C4 N3 C5 113.9(3) . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C6 N4 C18 118.4(3) . . ?
C6 N4 Cu1 134.4(2) . . ?
C18 N4 Cu1 106.3(2) . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 N5 C7 122.9(3) . . ?
C6 N5 C8 121.7(3) . . ?
C7 N5 C8 115.4(3) . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C6 N6 C9 123.1(3) . . ?
C6 N6 C10 121.3(3) . . ?
C9 N6 C10 113.9(3) . . ?
N4 C6 N6 120.3(3) . . ?
N4 C6 N5 122.7(3) . . ?
N6 C6 N5 116.9(3) . . ?
C11 N7 C20 118.1(3) . . ?
C11 N7 Cu1 134.4(3) . . ?
C20 N7 Cu1 105.4(2) . . ?
N5 C7 H7A 109.5 . . ?
N5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C11 N8 C12 120.6(3) . . ?
C11 N8 C13 122.2(3) . . ?
C12 N8 C13 114.5(3) . . ?
N5 C8 H8A 109.5 . . ?
N5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C11 N9 C15 121.2(3) . . ?
C11 N9 C14 123.5(3) . . ?
C15 N9 C14 115.0(3) . . ?
N6 C9 H9A 109.5 . . ?
N6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C17 N10 C21 109.8(3) . . ?
C17 N10 C19 111.0(3) . . ?
C21 N10 C19 110.8(3) . . ?
C17 N10 Cu1 108.3(2) . . ?
C21 N10 Cu1 109.1(2) . . ?
C19 N10 Cu1 107.9(2) . . ?
N6 C10 H10A 109.5 . . ?
N6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C22 N11 C37 119.6(3) . . ?
C22 N11 Cu2 132.9(2) . . ?
C37 N11 Cu2 106.3(2) . . ?
N7 C11 N8 120.8(3) . . ?
N7 C11 N9 123.7(4) . . ?
N8 C11 N9 115.4(3) . . ?
C22 N12 C24 122.7(3) . . ?
C22 N12 C23 120.1(3) . . ?
C24 N12 C23 115.0(3) . . ?
N8 C12 H12A 109.5 . . ?
N8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C22 N13 C26 123.2(3) . . ?
C22 N13 C25 122.1(3) . . ?
C26 N13 C25 114.7(3) . . ?
N8 C13 H13A 109.5 . . ?
N8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C27 N14 C39 118.3(3) . . ?
C27 N14 Cu2 134.5(2) . . ?
C39 N14 Cu2 106.9(2) . . ?
N9 C14 H14A 109.5 . . ?
N9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C27 N15 C31 122.9(3) . . ?
C27 N15 C30 121.4(3) . . ?
C31 N15 C30 115.7(3) . . ?
N9 C15 H15A 109.5 . . ?
N9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C27 N16 C28 120.7(3) . . ?
C27 N16 C29 123.1(3) . . ?
C28 N16 C29 114.6(3) . . ?
N1 C16 C17 106.1(3) . . ?
N1 C16 H16A 110.5 . . ?
C17 C16 H16A 110.5 . . ?
N1 C16 H16B 110.5 . . ?
C17 C16 H16B 110.5 . . ?
H16A C16 H16B 108.7 . . ?
C32 N17 C41 118.9(3) . . ?
C32 N17 Cu2 132.1(3) . . ?
C41 N17 Cu2 106.9(2) . . ?
N10 C17 C16 108.8(3) . . ?
N10 C17 H17A 109.9 . . ?
C16 C17 H17A 109.9 . . ?
N10 C17 H17B 109.9 . . ?
C16 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
C32 N18 C33 119.9(3) . . ?
C32 N18 C34 122.5(3) . . ?
C33 N18 C34 114.5(3) . . ?
N4 C18 C19 106.1(3) . . ?
N4 C18 H18A 110.5 . . ?
C19 C18 H18A 110.5 . . ?
N4 C18 H18B 110.5 . . ?
C19 C18 H18B 110.5 . . ?
H18A C18 H18B 108.7 . . ?
C32 N19 C35 124.6(3) . . ?
C32 N19 C36 121.1(3) . . ?
C35 N19 C36 114.3(3) . . ?
N10 C19 C18 108.8(3) . . ?
N10 C19 H19A 109.9 . . ?
C18 C19 H19A 109.9 . . ?
N10 C19 H19B 109.9 . . ?
C18 C19 H19B 109.9 . . ?
H19A C19 H19B 108.3 . . ?
C38 N20 C40 111.0(3) . . ?
C38 N20 C42 110.3(3) . . ?
C40 N20 C42 110.0(3) . . ?
C38 N20 Cu2 108.3(2) . . ?
C40 N20 Cu2 108.5(2) . . ?
C42 N20 Cu2 108.6(2) . . ?
N7 C20 C21 107.0(3) . . ?
N7 C20 H20A 110.3 . . ?
C21 C20 H20A 110.3 . . ?
N7 C20 H20B 110.3 . . ?
C21 C20 H20B 110.3 . . ?
H20A C20 H20B 108.6 . . ?
N10 C21 C20 109.6(3) . . ?
N10 C21 H21A 109.7 . . ?
C20 C21 H21A 109.7 . . ?
N10 C21 H21B 109.7 . . ?
C20 C21 H21B 109.7 . . ?
H21A C21 H21B 108.2 . . ?
N11 C22 N13 123.6(3) . . ?
N11 C22 N12 121.0(3) . . ?
N13 C22 N12 115.3(3) . . ?
N12 C23 H23A 109.5 . . ?
N12 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N12 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N12 C24 H24A 109.5 . . ?
N12 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N12 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N13 C25 H25A 109.5 . . ?
N13 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N13 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N13 C26 H26A 109.5 . . ?
N13 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N13 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N14 C27 N16 120.9(3) . . ?
N14 C27 N15 123.8(3) . . ?
N16 C27 N15 115.2(3) . . ?
N16 C28 H28A 109.5 . . ?
N16 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N16 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N16 C29 H29A 109.5 . . ?
N16 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N16 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N15 C30 H30A 109.5 . . ?
N15 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
N15 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N15 C31 H31A 109.5 . . ?
N15 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N15 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N17 C32 N18 120.8(3) . . ?
N17 C32 N19 123.4(3) . . ?
N18 C32 N19 115.7(3) . . ?
N18 C33 H33A 109.5 . . ?
N18 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
N18 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N18 C34 H34A 109.5 . . ?
N18 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
N18 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N19 C35 H35A 109.5 . . ?
N19 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
N19 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N19 C36 H36A 109.5 . . ?
N19 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N19 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N11 C37 C38 106.7(3) . . ?
N11 C37 H37A 110.4 . . ?
C38 C37 H37A 110.4 . . ?
N11 C37 H37B 110.4 . . ?
C38 C37 H37B 110.4 . . ?
H37A C37 H37B 108.6 . . ?
N20 C38 C37 108.7(3) . . ?
N20 C38 H38A 110.0 . . ?
C37 C38 H38A 110.0 . . ?
N20 C38 H38B 110.0 . . ?
C37 C38 H38B 110.0 . . ?
H38A C38 H38B 108.3 . . ?
N14 C39 C40 106.9(3) . . ?
N14 C39 H39A 110.3 . . ?
C40 C39 H39A 110.3 . . ?
N14 C39 H39B 110.3 . . ?
C40 C39 H39B 110.3 . . ?
H39A C39 H39B 108.6 . . ?
N20 C40 C39 109.4(3) . . ?
N20 C40 H40A 109.8 . . ?
C39 C40 H40A 109.8 . . ?
N20 C40 H40B 109.8 . . ?
C39 C40 H40B 109.8 . . ?
H40A C40 H40B 108.2 . . ?
N17 C41 C42 106.4(3) . . ?
N17 C41 H41A 110.5 . . ?
C42 C41 H41A 110.5 . . ?
N17 C41 H41B 110.5 . . ?
C42 C41 H41B 110.5 . . ?
H41A C41 H41B 108.6 . . ?
N20 C42 C41 109.9(3) . . ?
N20 C42 H42A 109.7 . . ?
C41 C42 H42A 109.7 . . ?
N20 C42 H42B 109.7 . . ?
C41 C42 H42B 109.7 . . ?
H42A C42 H42B 108.2 . . ?

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
C16 N1 C1 N2 145.5(3) . . . . ?
Cu1 N1 C1 N2 -42.7(5) . . . . ?
C16 N1 C1 N3 -31.6(5) . . . . ?
Cu1 N1 C1 N3 140.2(3) . . . . ?
N1 C1 N2 C2 -24.3(5) . . . . ?
N3 C1 N2 C2 153.0(3) . . . . ?
N1 C1 N2 C3 142.2(4) . . . . ?
N3 C1 N2 C3 -40.5(5) . . . . ?
N1 C1 N3 C4 143.8(4) . . . . ?
N2 C1 N3 C4 -33.4(5) . . . . ?
N1 C1 N3 C5 -34.2(6) . . . . ?
N2 C1 N3 C5 148.6(4) . . . . ?
C18 N4 C6 N6 148.6(3) . . . . ?
Cu1 N4 C6 N6 -44.1(5) . . . . ?
C18 N4 C6 N5 -28.3(5) . . . . ?
Cu1 N4 C6 N5 139.0(3) . . . . ?
C9 N6 C6 N4 142.3(4) . . . . ?
C10 N6 C6 N4 -22.1(5) . . . . ?
C9 N6 C6 N5 -40.7(5) . . . . ?
C10 N6 C6 N5 155.0(3) . . . . ?
C7 N5 C6 N4 -40.0(5) . . . . ?
C8 N5 C6 N4 143.6(4) . . . . ?
C7 N5 C6 N6 143.0(4) . . . . ?
C8 N5 C6 N6 -33.4(5) . . . . ?
C20 N7 C11 N8 151.9(3) . . . . ?
Cu1 N7 C11 N8 -47.2(5) . . . . ?
C20 N7 C11 N9 -24.0(6) . . . . ?
Cu1 N7 C11 N9 136.8(3) . . . . ?
C12 N8 C11 N7 -22.7(6) . . . . ?
C13 N8 C11 N7 137.7(4) . . . . ?
C12 N8 C11 N9 153.5(3) . . . . ?
C13 N8 C11 N9 -46.0(5) . . . . ?
C15 N9 C11 N7 -40.9(6) . . . . ?
C14 N9 C11 N7 145.6(4) . . . . ?
C15 N9 C11 N8 142.9(4) . . . . ?
C14 N9 C11 N8 -30.5(6) . . . . ?
C1 N1 C16 C17 -137.8(3) . . . . ?
Cu1 N1 C16 C17 48.6(3) . . . . ?
C21 N10 C17 C16 -84.0(4) . . . . ?
C19 N10 C17 C16 153.2(3) . . . . ?
Cu1 N10 C17 C16 35.0(3) . . . . ?
N1 C16 C17 N10 -55.5(4) . . . . ?
C6 N4 C18 C19 -136.7(3) . . . . ?
Cu1 N4 C18 C19 52.7(3) . . . . ?
C17 N10 C19 C18 -86.4(4) . . . . ?
C21 N10 C19 C18 151.4(3) . . . . ?
Cu1 N10 C19 C18 32.0(3) . . . . ?
N4 C18 C19 N10 -56.9(4) . . . . ?
C11 N7 C20 C21 -143.0(3) . . . . ?
Cu1 N7 C20 C21 51.1(3) . . . . ?
C17 N10 C21 C20 149.3(3) . . . . ?
C19 N10 C21 C20 -87.7(4) . . . . ?
Cu1 N10 C21 C20 30.9(3) . . . . ?
N7 C20 C21 N10 -55.9(4) . . . . ?
C37 N11 C22 N13 -28.9(5) . . . . ?
Cu2 N11 C22 N13 136.9(3) . . . . ?
C37 N11 C22 N12 147.8(3) . . . . ?
Cu2 N11 C22 N12 -46.4(5) . . . . ?
C26 N13 C22 N11 -33.5(5) . . . . ?
C25 N13 C22 N11 143.3(3) . . . . ?
C26 N13 C22 N12 149.7(3) . . . . ?
C25 N13 C22 N12 -33.6(5) . . . . ?
C24 N12 C22 N11 140.7(4) . . . . ?
C23 N12 C22 N11 -21.6(5) . . . . ?
C24 N12 C22 N13 -42.3(5) . . . . ?
C23 N12 C22 N13 155.4(3) . . . . ?
C39 N14 C27 N16 149.1(3) . . . . ?
Cu2 N14 C27 N16 -38.2(5) . . . . ?
C39 N14 C27 N15 -27.9(5) . . . . ?
Cu2 N14 C27 N15 144.7(3) . . . . ?
C28 N16 C27 N14 -26.1(5) . . . . ?
C29 N16 C27 N14 138.6(4) . . . . ?
C28 N16 C27 N15 151.2(3) . . . . ?
C29 N16 C27 N15 -44.1(5) . . . . ?
C31 N15 C27 N14 -34.3(6) . . . . ?
C30 N15 C27 N14 144.4(4) . . . . ?
C31 N15 C27 N16 148.5(3) . . . . ?
C30 N15 C27 N16 -32.9(5) . . . . ?
C41 N17 C32 N18 148.2(3) . . . . ?
Cu2 N17 C32 N18 -50.7(5) . . . . ?
C41 N17 C32 N19 -28.4(5) . . . . ?
Cu2 N17 C32 N19 132.7(3) . . . . ?
C33 N18 C32 N17 -21.8(5) . . . . ?
C34 N18 C32 N17 137.2(4) . . . . ?
C33 N18 C32 N19 155.0(3) . . . . ?
C34 N18 C32 N19 -46.0(5) . . . . ?
C35 N19 C32 N17 147.3(4) . . . . ?
C36 N19 C32 N17 -33.3(6) . . . . ?
C35 N19 C32 N18 -29.4(5) . . . . ?
C36 N19 C32 N18 150.0(4) . . . . ?
C22 N11 C37 C38 -140.0(3) . . . . ?
Cu2 N11 C37 C38 50.8(3) . . . . ?
C40 N20 C38 C37 153.3(3) . . . . ?
C42 N20 C38 C37 -84.5(4) . . . . ?
Cu2 N20 C38 C37 34.3(3) . . . . ?
N11 C37 C38 N20 -57.5(4) . . . . ?
C27 N14 C39 C40 -136.3(3) . . . . ?
Cu2 N14 C39 C40 49.2(3) . . . . ?
C38 N20 C40 C39 -85.5(4) . . . . ?
C42 N20 C40 C39 152.1(3) . . . . ?
Cu2 N20 C40 C39 33.5(3) . . . . ?
N14 C39 C40 N20 -55.8(4) . . . . ?
C32 N17 C41 C42 -144.1(3) . . . . ?
Cu2 N17 C41 C42 50.5(3) . . . . ?
C38 N20 C42 C41 150.3(3) . . . . ?
C40 N20 C42 C41 -86.9(4) . . . . ?
Cu2 N20 C42 C41 31.7(3) . . . . ?
N17 C41 C42 N20 -55.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2B Br1 0.98 2.87 3.555(4) 128.0 . yes
C10 H10B Br1 0.98 2.84 3.567(4) 131.8 . yes
C12 H12B Br1 0.98 2.87 3.617(4) 134.0 . yes
C23 H23B Br2 0.98 2.81 3.545(4) 132.6 . yes
C28 H28B Br2 0.98 2.82 3.556(4) 132.8 . yes
C30 H30A Br4 0.98 2.92 3.785(4) 147.7 . yes
C33 H33B Br2 0.98 2.89 3.634(4) 133.1 . yes

_refine_diff_density_max         1.174
_refine_diff_density_min         -0.820
_refine_diff_density_rms         0.149


####################################################################### 
# 
# 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_C1
_database_code_depnum_ccdc_archive 'CCDC 2289694'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2023-08-20 deposited with the CCDC.	2024-01-04 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         'C23 H38 Br Cu N8, Br'
_chemical_formula_sum            'C23 H38 Br2 Cu N8'
_chemical_formula_weight         649.97

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   8.4759(17)
_cell_length_b                   22.426(5)
_cell_length_c                   14.174(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.99(3)
_cell_angle_gamma                90
_cell_volume                     2679.6(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    54386
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      33.18

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_F_000             1324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    3.825
_shelx_estimated_absorpt_T_min   0.501
_shelx_estimated_absorpt_T_max   0.616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1534
_exptl_absorpt_correction_T_max  0.3712
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270.
;
_exptl_absorpt_special_details   
;
Afterwards scaling of reflection intensities was performed within STOE LANA.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;

_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'

_diffrn_detector                 Pilatus200K
_diffrn_detector_type            'DECTRIS PILATUS 200K'
_diffrn_detector_area_resol_mean 5.81

_diffrn_source                   'Genix Mo'
_diffrn_source_type              ?
_diffrn_radiation_probe          x-ray
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'

_diffrn_ambient_temperature      100

_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 3145 frames, detector distance = 80 mm
;


_diffrn_reflns_number            29466
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.890
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4973
_reflns_number_gt                4728
_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       
;
X-Area Pilatus3_SV 1.31.131.0 (STOE, 2017)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
X-Area Integrate 1.71.0.0 (STOE, 2016)
X-Area LANA 1.71.4.0 (STOE, 2017)
;

_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.77, Darmstadt 2016
;

_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)+(0.0094P)²+7.0749P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         4973
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0651
_refine_ls_wR_factor_gt          0.0632
_refine_ls_goodness_of_fit_ref   1.271
_refine_ls_restrained_S_all      1.271
_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
Br1 Br 0.32040(3) 0.49387(2) 0.72167(2) 0.01419(8) Uani 1 1 d . . . . .
Cu1 Cu 0.57159(4) 0.52582(2) 0.66862(2) 0.01038(8) Uani 1 1 d . . . . .
C1 C 0.6230(3) 0.58921(12) 0.8718(2) 0.0133(6) Uani 1 1 d . . . . .
N1 N 0.6744(3) 0.57859(11) 0.78959(17) 0.0131(5) Uani 1 1 d . . . . .
Br2 Br 0.58185(4) 0.23787(2) 0.96561(2) 0.02300(9) Uani 1 1 d . . . . .
C2 C 0.8275(4) 0.53369(14) 0.9723(2) 0.0223(7) Uani 1 1 d . . . . .
H2A H 0.807063 0.502993 0.923350 0.033 Uiso 1 1 calc R U . . .
H2B H 0.823596 0.515717 1.035038 0.033 Uiso 1 1 calc R U . . .
H2C H 0.932581 0.551119 0.968287 0.033 Uiso 1 1 calc R U . . .
N2 N 0.4740(3) 0.61182(11) 0.87524(18) 0.0155(5) Uani 1 1 d . . . . .
C3 C 0.6961(4) 0.61837(15) 1.0398(2) 0.0235(7) Uani 1 1 d . . . . .
H3A H 0.799880 0.636196 1.059405 0.035 Uiso 1 1 calc R U . . .
H3B H 0.661912 0.594718 1.092135 0.035 Uiso 1 1 calc R U . . .
H3C H 0.618510 0.650030 1.022925 0.035 Uiso 1 1 calc R U . . .
N3 N 0.7078(3) 0.57996(12) 0.95785(18) 0.0177(5) Uani 1 1 d . . . . .
N4 N 0.7839(3) 0.54704(10) 0.61373(16) 0.0110(5) Uani 1 1 d . . . . .
C4 C 0.3972(4) 0.64749(14) 0.7984(2) 0.0189(6) Uani 1 1 d . . . . .
H4A H 0.474958 0.658672 0.755060 0.028 Uiso 1 1 calc R U . . .
H4B H 0.352894 0.683588 0.824412 0.028 Uiso 1 1 calc R U . . .
H4C H 0.311663 0.624323 0.763926 0.028 Uiso 1 1 calc R U . . .
N5 N 0.4828(3) 0.58293(11) 0.56740(17) 0.0130(5) Uani 1 1 d . . . . .
C5 C 0.3713(4) 0.59466(16) 0.9466(2) 0.0238(7) Uani 1 1 d . . . . .
H5A H 0.272082 0.578285 0.915420 0.036 Uiso 1 1 calc R U . . .
H5B H 0.348078 0.629719 0.984052 0.036 Uiso 1 1 calc R U . . .
H5C H 0.424590 0.564410 0.988481 0.036 Uiso 1 1 calc R U . . .
N8 N 1.0082(3) 0.31523(11) 0.80741(18) 0.0152(5) Uani 1 1 d . . . . .
C8 C 0.4085(3) 0.67786(13) 0.4381(2) 0.0126(6) Uani 1 1 d . . . . .
N7 N 0.6952(3) 0.45233(10) 0.71338(17) 0.0117(5) Uani 1 1 d . . . . .
C7 C 0.5582(3) 0.64973(13) 0.4474(2) 0.0137(6) Uani 1 1 d . . . . .
H7 H 0.638033 0.662514 0.409600 0.016 Uiso 1 1 calc R U . . .
N6 N 0.3786(3) 0.72433(12) 0.37920(18) 0.0169(5) Uani 1 1 d . . . . .
C6 C 0.5886(3) 0.60386(13) 0.5110(2) 0.0133(6) Uani 1 1 d . . . . .
C9 C 0.2959(3) 0.65499(13) 0.4963(2) 0.0134(6) Uani 1 1 d . . . . .
H9 H 0.191867 0.671212 0.492456 0.016 Uiso 1 1 calc R U . . .
C10 C 0.3383(3) 0.60945(13) 0.5580(2) 0.0128(6) Uani 1 1 d . . . . .
H10 H 0.261362 0.595488 0.596931 0.015 Uiso 1 1 calc R U . . .
C11 C 0.4977(4) 0.74429(15) 0.3188(2) 0.0229(7) Uani 1 1 d . . . . .
H11A H 0.533564 0.710277 0.283282 0.034 Uiso 1 1 calc R U . . .
H11B H 0.588125 0.761488 0.358304 0.034 Uiso 1 1 calc R U . . .
H11C H 0.451171 0.774523 0.274347 0.034 Uiso 1 1 calc R U . . .
C12 C 0.2310(4) 0.75763(14) 0.3740(2) 0.0194(6) Uani 1 1 d . . . . .
H12A H 0.242321 0.794824 0.339084 0.029 Uiso 1 1 calc R U . . .
H12B H 0.205523 0.766841 0.438318 0.029 Uiso 1 1 calc R U . . .
H12C H 0.145390 0.733683 0.341210 0.029 Uiso 1 1 calc R U . . .
C13 C 0.8410(3) 0.44762(12) 0.6840(2) 0.0111(6) Uani 1 1 d . . . . .
C14 C 0.9474(3) 0.40329(13) 0.7129(2) 0.0125(6) Uani 1 1 d . . . . .
H14 H 1.048306 0.402174 0.689382 0.015 Uiso 1 1 calc R U . . .
C15 C 0.9067(3) 0.35955(13) 0.7775(2) 0.0125(6) Uani 1 1 d . . . . .
C16 C 0.7544(4) 0.36505(13) 0.8096(2) 0.0153(6) Uani 1 1 d . . . . .
H16 H 0.720722 0.337412 0.854219 0.018 Uiso 1 1 calc R U . . .
C17 C 0.6560(3) 0.41059(13) 0.7759(2) 0.0136(6) Uani 1 1 d . . . . .
H17 H 0.554022 0.412982 0.797799 0.016 Uiso 1 1 calc R U . . .
C18 C 1.1568(3) 0.30772(14) 0.7646(2) 0.0167(6) Uani 1 1 d . . . . .
H18A H 1.133315 0.296984 0.697579 0.025 Uiso 1 1 calc R U . . .
H18B H 1.219810 0.276000 0.797834 0.025 Uiso 1 1 calc R U . . .
H18C H 1.216850 0.345131 0.769694 0.025 Uiso 1 1 calc R U . . .
C19 C 0.9666(4) 0.27175(14) 0.8771(2) 0.0215(7) Uani 1 1 d . . . . .
H19A H 0.873676 0.248914 0.850819 0.032 Uiso 1 1 calc R U . . .
H19B H 0.942066 0.292531 0.934649 0.032 Uiso 1 1 calc R U . . .
H19C H 1.056051 0.244584 0.892792 0.032 Uiso 1 1 calc R U . . .
C20 C 0.8615(3) 0.59397(13) 0.6771(2) 0.0144(6) Uani 1 1 d . . . . .
H20A H 0.812560 0.633136 0.660216 0.017 Uiso 1 1 calc R U . . .
H20B H 0.975439 0.596352 0.667811 0.017 Uiso 1 1 calc R U . . .
C21 C 0.8444(3) 0.58037(14) 0.7804(2) 0.0152(6) Uani 1 1 d . . . . .
H21A H 0.893988 0.541524 0.798617 0.018 Uiso 1 1 calc R U . . .
H21B H 0.896372 0.611727 0.821822 0.018 Uiso 1 1 calc R U . . .
C22 C 0.7452(3) 0.57205(14) 0.5171(2) 0.0154(6) Uani 1 1 d . . . . .
H22A H 0.740271 0.539484 0.469710 0.019 Uiso 1 1 calc R U . . .
H22B H 0.829392 0.600232 0.502704 0.019 Uiso 1 1 calc R U . . .
C23 C 0.8816(3) 0.49264(13) 0.6118(2) 0.0134(6) Uani 1 1 d . . . . .
H23A H 0.995071 0.503510 0.624385 0.016 Uiso 1 1 calc R U . . .
H23B H 0.865184 0.474588 0.547748 0.016 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Cu1 2.4384(7) . ?
Cu1 N5 2.010(2) . ?
Cu1 N7 2.020(2) . ?
Cu1 N4 2.088(2) . ?
Cu1 N1 2.188(2) . ?
C1 N1 1.308(4) . ?
C1 N3 1.366(4) . ?
C1 N2 1.367(4) . ?
N1 C21 1.460(4) . ?
C2 N3 1.451(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N2 C4 1.450(4) . ?
N2 C5 1.453(4) . ?
C3 N3 1.458(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
N4 C23 1.477(4) . ?
N4 C22 1.485(4) . ?
N4 C20 1.492(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N5 C6 1.347(4) . ?
N5 C10 1.355(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
N8 C15 1.353(4) . ?
N8 C19 1.457(4) . ?
N8 C18 1.464(4) . ?
C8 N6 1.343(4) . ?
C8 C7 1.411(4) . ?
C8 C9 1.421(4) . ?
N7 C13 1.348(4) . ?
N7 C17 1.354(4) . ?
C7 C6 1.374(4) . ?
C7 H7 0.9500 . ?
N6 C12 1.453(4) . ?
N6 C11 1.460(4) . ?
C6 C22 1.502(4) . ?
C9 C10 1.368(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.376(4) . ?
C13 C23 1.503(4) . ?
C14 C15 1.409(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.419(4) . ?
C16 C17 1.373(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.516(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?

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
N5 Cu1 N7 152.59(10) . . ?
N5 Cu1 N4 82.07(10) . . ?
N7 Cu1 N4 82.18(9) . . ?
N5 Cu1 N1 107.68(10) . . ?
N7 Cu1 N1 92.52(9) . . ?
N4 Cu1 N1 83.13(9) . . ?
N5 Cu1 Br1 97.66(7) . . ?
N7 Cu1 Br1 95.99(7) . . ?
N4 Cu1 Br1 174.73(7) . . ?
N1 Cu1 Br1 101.92(7) . . ?
N1 C1 N3 125.1(3) . . ?
N1 C1 N2 119.7(3) . . ?
N3 C1 N2 115.2(3) . . ?
C1 N1 C21 119.9(2) . . ?
C1 N1 Cu1 130.8(2) . . ?
C21 N1 Cu1 105.11(17) . . ?
N3 C2 H2A 109.5 . . ?
N3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 N2 C4 121.5(2) . . ?
C1 N2 C5 123.3(3) . . ?
C4 N2 C5 114.5(3) . . ?
N3 C3 H3A 109.5 . . ?
N3 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N3 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 N3 C2 122.0(3) . . ?
C1 N3 C3 123.3(3) . . ?
C2 N3 C3 114.5(3) . . ?
C23 N4 C22 111.4(2) . . ?
C23 N4 C20 112.4(2) . . ?
C22 N4 C20 109.3(2) . . ?
C23 N4 Cu1 109.02(17) . . ?
C22 N4 Cu1 108.31(17) . . ?
C20 N4 Cu1 106.21(17) . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 N5 C10 116.1(2) . . ?
C6 N5 Cu1 115.01(19) . . ?
C10 N5 Cu1 128.1(2) . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C15 N8 C19 120.9(2) . . ?
C15 N8 C18 120.1(2) . . ?
C19 N8 C18 118.9(2) . . ?
N6 C8 C7 120.9(3) . . ?
N6 C8 C9 123.2(3) . . ?
C7 C8 C9 115.9(3) . . ?
C13 N7 C17 116.3(2) . . ?
C13 N7 Cu1 115.40(19) . . ?
C17 N7 Cu1 127.96(19) . . ?
C6 C7 C8 120.1(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C8 N6 C12 122.4(3) . . ?
C8 N6 C11 120.4(2) . . ?
C12 N6 C11 117.2(2) . . ?
N5 C6 C7 124.0(3) . . ?
N5 C6 C22 116.1(3) . . ?
C7 C6 C22 119.8(3) . . ?
C10 C9 C8 119.5(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
N5 C10 C9 124.4(3) . . ?
N5 C10 H10 117.8 . . ?
C9 C10 H10 117.8 . . ?
N6 C11 H11A 109.5 . . ?
N6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N6 C12 H12A 109.5 . . ?
N6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N7 C13 C14 123.9(3) . . ?
N7 C13 C23 116.1(2) . . ?
C14 C13 C23 119.9(3) . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
N8 C15 C14 121.6(3) . . ?
N8 C15 C16 122.2(3) . . ?
C14 C15 C16 116.2(3) . . ?
C17 C16 C15 119.5(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
N7 C17 C16 124.1(3) . . ?
N7 C17 H17 117.9 . . ?
C16 C17 H17 117.9 . . ?
N8 C18 H18A 109.5 . . ?
N8 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N8 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N8 C19 H19A 109.5 . . ?
N8 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N8 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N4 C20 C21 111.0(2) . . ?
N4 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
N4 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
N1 C21 C20 106.6(2) . . ?
N1 C21 H21A 110.4 . . ?
C20 C21 H21A 110.4 . . ?
N1 C21 H21B 110.4 . . ?
C20 C21 H21B 110.4 . . ?
H21A C21 H21B 108.6 . . ?
N4 C22 C6 110.0(2) . . ?
N4 C22 H22A 109.7 . . ?
C6 C22 H22A 109.7 . . ?
N4 C22 H22B 109.7 . . ?
C6 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
N4 C23 C13 111.9(2) . . ?
N4 C23 H23A 109.2 . . ?
C13 C23 H23A 109.2 . . ?
N4 C23 H23B 109.2 . . ?
C13 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C1 N1 C21 -26.6(4) . . . . ?
N2 C1 N1 C21 152.8(3) . . . . ?
N3 C1 N1 Cu1 126.9(3) . . . . ?
N2 C1 N1 Cu1 -53.7(4) . . . . ?
N1 C1 N2 C4 -26.8(4) . . . . ?
N3 C1 N2 C4 152.7(3) . . . . ?
N1 C1 N2 C5 142.9(3) . . . . ?
N3 C1 N2 C5 -37.6(4) . . . . ?
N1 C1 N3 C2 -29.8(4) . . . . ?
N2 C1 N3 C2 150.8(3) . . . . ?
N1 C1 N3 C3 144.8(3) . . . . ?
N2 C1 N3 C3 -34.7(4) . . . . ?
N6 C8 C7 C6 177.2(3) . . . . ?
C9 C8 C7 C6 -1.1(4) . . . . ?
C7 C8 N6 C12 -174.5(3) . . . . ?
C9 C8 N6 C12 3.7(4) . . . . ?
C7 C8 N6 C11 4.0(4) . . . . ?
C9 C8 N6 C11 -177.8(3) . . . . ?
C10 N5 C6 C7 0.7(4) . . . . ?
Cu1 N5 C6 C7 -169.8(2) . . . . ?
C10 N5 C6 C22 -176.4(3) . . . . ?
Cu1 N5 C6 C22 13.1(3) . . . . ?
C8 C7 C6 N5 -0.1(4) . . . . ?
C8 C7 C6 C22 176.9(3) . . . . ?
N6 C8 C9 C10 -176.6(3) . . . . ?
C7 C8 C9 C10 1.6(4) . . . . ?
C6 N5 C10 C9 -0.1(4) . . . . ?
Cu1 N5 C10 C9 169.0(2) . . . . ?
C8 C9 C10 N5 -1.1(4) . . . . ?
C17 N7 C13 C14 0.8(4) . . . . ?
Cu1 N7 C13 C14 174.8(2) . . . . ?
C17 N7 C13 C23 177.7(2) . . . . ?
Cu1 N7 C13 C23 -8.3(3) . . . . ?
N7 C13 C14 C15 -0.4(4) . . . . ?
C23 C13 C14 C15 -177.2(3) . . . . ?
C19 N8 C15 C14 177.5(3) . . . . ?
C18 N8 C15 C14 -7.1(4) . . . . ?
C19 N8 C15 C16 -1.9(4) . . . . ?
C18 N8 C15 C16 173.4(3) . . . . ?
C13 C14 C15 N8 179.9(3) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
N8 C15 C16 C17 -179.3(3) . . . . ?
C14 C15 C16 C17 1.2(4) . . . . ?
C13 N7 C17 C16 -0.1(4) . . . . ?
Cu1 N7 C17 C16 -173.2(2) . . . . ?
C15 C16 C17 N7 -0.9(5) . . . . ?
C23 N4 C20 C21 -78.3(3) . . . . ?
C22 N4 C20 C21 157.4(2) . . . . ?
Cu1 N4 C20 C21 40.8(3) . . . . ?
C1 N1 C21 C20 -155.3(3) . . . . ?
Cu1 N1 C21 C20 45.2(2) . . . . ?
N4 C20 C21 N1 -60.1(3) . . . . ?
C23 N4 C22 C6 150.5(2) . . . . ?
C20 N4 C22 C6 -84.7(3) . . . . ?
Cu1 N4 C22 C6 30.6(3) . . . . ?
N5 C6 C22 N4 -29.7(4) . . . . ?
C7 C6 C22 N4 153.0(3) . . . . ?
C22 N4 C23 C13 -144.3(2) . . . . ?
C20 N4 C23 C13 92.6(3) . . . . ?
Cu1 N4 C23 C13 -24.9(3) . . . . ?
N7 C13 C23 N4 22.7(3) . . . . ?
C14 C13 C23 N4 -160.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3A N8 0.98 2.60 3.473(4) 148.5 3_767 yes
C9 H9 Br2 0.95 2.87 3.789(3) 162.1 2_556 yes
C10 H10 Br1 0.95 2.90 3.492(3) 121.9 . yes
C12 H12C N8 0.98 2.60 3.508(4) 154.0 3_666 yes
C22 H22A Br1 0.99 2.81 3.682(3) 147.3 3_666 yes
C17 H17 Br1 0.95 2.82 3.423(3) 122.6 . yes

_refine_diff_density_max         0.616
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.081


