# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_C1A
_database_code_depnum_ccdc_archive 'CCDC 2118638'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-07-28 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         'C26 H46 Cu N10, 2(Br)'
_chemical_formula_sum            'C26 H46 Br2 Cu N10'
_chemical_formula_weight         722.09

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      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                   9.2630(19)
_cell_length_b                   9.5980(19)
_cell_length_c                   10.712(2)
_cell_angle_alpha                77.80(3)
_cell_angle_beta                 66.20(3)
_cell_angle_gamma                83.30(3)
_cell_volume                     851.2(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    32477
_cell_measurement_theta_min      2.11
_cell_measurement_theta_max      33.96

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             371
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    3.020
_shelx_estimated_absorpt_T_min   0.418
_shelx_estimated_absorpt_T_max   0.531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0831
_exptl_absorpt_correction_T_max  0.1544
_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.
Finally a spherical absorption correction was done within STOE LANA.
;

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

_diffrn_detector                 'Hybrid Pixel Counting Detector'
_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      
; 2814 frames, detector distance = 60 mm
;

_diffrn_reflns_number            16399
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.113
_diffrn_reflns_theta_max         32.031
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5899
_reflns_number_gt                5343
_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    'SHELXS-97 (Sheldrick, 1990)'
_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 1.77, 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)+(0.1117P)²+2.7955P] 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         5899
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0757
_refine_ls_wR_factor_ref         0.2248
_refine_ls_wR_factor_gt          0.2163
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 1.000000 0.000000 0.01945(15) Uani 1 2 d S . P . .
C1 C 0.2906(4) 0.7539(4) 0.1729(3) 0.0217(5) Uani 1 1 d . . . . .
N1 N 0.4207(3) 0.8247(3) 0.1317(3) 0.0209(5) Uani 1 1 d . . . . .
C2 C 0.1310(4) 0.9748(4) 0.1535(4) 0.0293(7) Uani 1 1 d . . . . .
H2A H 0.019356 0.995425 0.207475 0.044 Uiso 1 1 calc R U . . .
H2B H 0.158600 1.021363 0.056552 0.044 Uiso 1 1 calc R U . . .
H2C H 0.196427 1.010914 0.191480 0.044 Uiso 1 1 calc R U . . .
C13 C 0.7965(5) 1.1421(5) 0.4715(4) 0.0319(7) Uani 1 1 d . . . . .
H13A H 0.817546 1.122506 0.556314 0.048 Uiso 1 1 calc R U . . .
H13B H 0.713237 1.216718 0.479068 0.048 Uiso 1 1 calc R U . . .
H13C H 0.892980 1.174072 0.391660 0.048 Uiso 1 1 calc R U . . .
Br2 Br 0.13889(8) 0.33612(8) 0.09926(8) 0.02878(18) Uani 0.5 1 d . . P . .
N2 N 0.1584(3) 0.8220(3) 0.1611(3) 0.0264(6) Uani 1 1 d . . . . .
C3 C 0.0510(5) 0.7511(5) 0.1276(5) 0.0364(8) Uani 1 1 d . . . . .
H3A H 0.041197 0.805420 0.042804 0.055 Uiso 1 1 calc R U . . .
H3B H -0.053017 0.745730 0.204274 0.055 Uiso 1 1 calc R U . . .
H3C H 0.092675 0.654547 0.113240 0.055 Uiso 1 1 calc R U . . .
N3 N 0.2810(4) 0.6135(3) 0.2298(3) 0.0259(6) Uani 1 1 d . . . . .
N4 N 0.5725(3) 1.0274(3) 0.1445(3) 0.0219(5) Uani 1 1 d . . . . .
C4 C 0.4118(5) 0.5114(4) 0.1847(4) 0.0297(7) Uani 1 1 d . . . . .
H4A H 0.374751 0.428703 0.167268 0.045 Uiso 1 1 calc R U . . .
H4B H 0.453734 0.480308 0.257111 0.045 Uiso 1 1 calc R U . . .
H4C H 0.495117 0.556360 0.099201 0.045 Uiso 1 1 calc R U . . .
C5 C 0.1409(5) 0.5542(5) 0.3475(5) 0.0371(9) Uani 1 1 d . . . . .
H5A H 0.172249 0.499378 0.421303 0.056 Uiso 1 1 calc R U . . .
H5B H 0.089904 0.491556 0.317367 0.056 Uiso 1 1 calc R U . . .
H5C H 0.066878 0.632061 0.382485 0.056 Uiso 1 1 calc R U . . .
N5 N 0.7456(4) 1.0122(4) 0.4529(3) 0.0281(6) Uani 1 1 d . . . . .
C7 C 0.5809(4) 0.9036(3) 0.2304(3) 0.0203(5) Uani 1 1 d . . . . .
C6 C 0.5290(4) 0.7754(3) 0.2016(3) 0.0226(6) Uani 1 1 d . . . . .
H6A H 0.621655 0.724055 0.141978 0.027 Uiso 1 1 calc R U . . .
H6AB H 0.475259 0.709412 0.289619 0.027 Uiso 1 1 calc R U . . .
C8 C 0.6363(4) 0.8938(4) 0.3334(3) 0.0224(6) Uani 1 1 d . . . . .
H8 H 0.640189 0.804339 0.390578 0.027 Uiso 1 1 calc R U . . .
C9 C 0.6872(4) 1.0167(4) 0.3539(3) 0.0233(6) Uani 1 1 d . . . . .
C10 C 0.6760(4) 1.1466(4) 0.2650(4) 0.0255(6) Uani 1 1 d . . . . .
H10 H 0.707535 1.233050 0.274661 0.031 Uiso 1 1 calc R U . . .
C11 C 0.6192(4) 1.1458(4) 0.1651(4) 0.0247(6) Uani 1 1 d . . . . .
H11 H 0.612254 1.233724 0.106862 0.030 Uiso 1 1 calc R U . . .
C12 C 0.7652(5) 0.8765(5) 0.5363(4) 0.0320(7) Uani 1 1 d . . . . .
H12A H 0.812402 0.891896 0.599137 0.048 Uiso 1 1 calc R U . . .
H12B H 0.834472 0.812026 0.475380 0.048 Uiso 1 1 calc R U . . .
H12C H 0.662012 0.834029 0.590675 0.048 Uiso 1 1 calc R U . . .
Br1 Br 0.500000 0.500000 0.500000 0.0493(3) Uani 0.824(3) 2 d S . P A 1
Br1' Br 0.1958(7) 0.5179(7) 0.8103(12) 0.087(4) Uani 0.0878(16) 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.952(3) 2_675 ?
Cu1 N1 1.952(3) . ?
Cu1 N4 1.992(3) . ?
Cu1 N4 1.992(3) 2_675 ?
C1 N1 1.321(4) . ?
C1 N3 1.354(4) . ?
C1 N2 1.359(4) . ?
N1 C6 1.462(4) . ?
C2 N2 1.450(5) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C13 N5 1.461(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N2 C3 1.460(5) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
N3 C4 1.454(5) . ?
N3 C5 1.465(5) . ?
N4 C11 1.350(4) . ?
N4 C7 1.356(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
N5 C9 1.363(4) . ?
N5 C12 1.453(5) . ?
C7 C8 1.375(4) . ?
C7 C6 1.502(5) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C8 C9 1.409(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.421(5) . ?
C10 C11 1.372(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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 N1 180.0 2_675 . ?
N1 Cu1 N4 98.05(12) 2_675 . ?
N1 Cu1 N4 81.95(12) . . ?
N1 Cu1 N4 81.95(12) 2_675 2_675 ?
N1 Cu1 N4 98.05(12) . 2_675 ?
N4 Cu1 N4 180.0 . 2_675 ?
N1 C1 N3 122.6(3) . . ?
N1 C1 N2 120.3(3) . . ?
N3 C1 N2 117.1(3) . . ?
C1 N1 C6 118.0(3) . . ?
C1 N1 Cu1 133.3(2) . . ?
C6 N1 Cu1 108.4(2) . . ?
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 . . ?
N5 C13 H13A 109.5 . . ?
N5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 N2 C2 122.3(3) . . ?
C1 N2 C3 121.5(3) . . ?
C2 N2 C3 115.1(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 . . ?
C1 N3 C4 122.8(3) . . ?
C1 N3 C5 122.5(3) . . ?
C4 N3 C5 114.7(3) . . ?
C11 N4 C7 117.0(3) . . ?
C11 N4 Cu1 130.5(2) . . ?
C7 N4 Cu1 112.5(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 . . ?
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 . . ?
C9 N5 C12 120.1(3) . . ?
C9 N5 C13 120.6(3) . . ?
C12 N5 C13 119.3(3) . . ?
N4 C7 C8 123.3(3) . . ?
N4 C7 C6 114.6(3) . . ?
C8 C7 C6 122.1(3) . . ?
N1 C6 C7 108.1(3) . . ?
N1 C6 H6A 110.1 . . ?
C7 C6 H6A 110.1 . . ?
N1 C6 H6AB 110.1 . . ?
C7 C6 H6AB 110.1 . . ?
H6A C6 H6AB 108.4 . . ?
C7 C8 C9 119.9(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
N5 C9 C8 122.1(3) . . ?
N5 C9 C10 121.2(3) . . ?
C8 C9 C10 116.6(3) . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
N4 C11 C10 123.9(3) . . ?
N4 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
N5 C12 H12A 109.5 . . ?
N5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
N3 C1 N1 C6 -28.1(5) . . . . ?
N2 C1 N1 C6 150.9(3) . . . . ?
N3 C1 N1 Cu1 157.8(3) . . . . ?
N2 C1 N1 Cu1 -23.2(5) . . . . ?
N1 C1 N2 C2 -23.1(5) . . . . ?
N3 C1 N2 C2 155.9(3) . . . . ?
N1 C1 N2 C3 144.5(4) . . . . ?
N3 C1 N2 C3 -36.5(5) . . . . ?
N1 C1 N3 C4 -36.3(5) . . . . ?
N2 C1 N3 C4 144.7(3) . . . . ?
N1 C1 N3 C5 139.9(4) . . . . ?
N2 C1 N3 C5 -39.0(5) . . . . ?
C11 N4 C7 C8 -1.2(5) . . . . ?
Cu1 N4 C7 C8 176.2(3) . . . . ?
C11 N4 C7 C6 -179.4(3) . . . . ?
Cu1 N4 C7 C6 -2.0(3) . . . . ?
C1 N1 C6 C7 -135.8(3) . . . . ?
Cu1 N1 C6 C7 39.6(3) . . . . ?
N4 C7 C6 N1 -24.6(4) . . . . ?
C8 C7 C6 N1 157.1(3) . . . . ?
N4 C7 C8 C9 0.3(5) . . . . ?
C6 C7 C8 C9 178.4(3) . . . . ?
C12 N5 C9 C8 3.4(5) . . . . ?
C13 N5 C9 C8 -179.7(3) . . . . ?
C12 N5 C9 C10 -176.0(3) . . . . ?
C13 N5 C9 C10 0.8(5) . . . . ?
C7 C8 C9 N5 -178.8(3) . . . . ?
C7 C8 C9 C10 0.6(5) . . . . ?
N5 C9 C10 C11 178.8(3) . . . . ?
C8 C9 C10 C11 -0.7(5) . . . . ?
C7 N4 C11 C10 1.1(5) . . . . ?
Cu1 N4 C11 C10 -175.7(3) . . . . ?
C9 C10 C11 N4 -0.2(5) . . . . ?

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 N4 0.98 2.62 3.267(5) 123.4 2_675 yes
C4 H4A Br2 0.98 2.85 3.683(4) 143.8 . yes
C4 H4B Br1^a 0.98 2.85 3.760(4) 155.1 . yes
C5 H5B Br2 0.98 2.89 3.722(5) 143.3 . yes
C6 H6A Br2 0.99 2.76 3.699(4) 157.9 2_665 yes
C6 H6A Br1'^b 0.99 2.79 3.558(9) 134.6 2_666 yes
C6 H6AB Br1^a 0.99 2.75 3.630(4) 148.3 . yes
C10 H10 Br1'^b 0.95 2.50 3.385(7) 154.3 2_676 yes

_refine_diff_density_max         2.412
_refine_diff_density_min         -1.835
_refine_diff_density_rms         0.177


####################################################################### 
# 
# 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 2118645'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H36 Cu N8, 2(Br)'
_chemical_formula_sum            'C22 H36 Br2 Cu N8'
_chemical_formula_weight         635.95

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0168(7)
_cell_length_b                   9.9820(7)
_cell_length_c                   14.8745(10)
_cell_angle_alpha                77.378(6)
_cell_angle_beta                 86.558(6)
_cell_angle_gamma                87.412(6)
_cell_volume                     1303.37(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4349
_cell_measurement_theta_min      2.2539
_cell_measurement_theta_max      29.1178

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             646
_exptl_absorpt_coefficient_mu    3.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73446
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0560
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11081
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0970
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4817
_reflns_number_gt                3083
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0829P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4817
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1783
_refine_ls_wR_factor_gt          0.1748
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_restrained_S_all      1.188
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 1.0000 0.0000 0.0164(3) Uani 1 2 d S . .
Br1 Br 0.34396(9) 0.21686(10) 0.08480(7) 0.0369(3) Uani 1 1 d . . .
N1 N 0.1292(6) 0.8687(6) 0.0756(4) 0.0159(14) Uani 1 1 d . . .
C1 C 0.2106(8) 0.7647(8) 0.0566(5) 0.0160(17) Uani 1 1 d . . .
Cu2 Cu 0.0000 0.5000 0.5000 0.0169(3) Uani 1 2 d S . .
Br2 Br 0.32114(10) 0.73750(10) 0.38638(6) 0.0352(3) Uani 1 1 d . . .
N2 N 0.3351(6) 0.7217(6) 0.1012(4) 0.0160(14) Uani 1 1 d . . .
C2 C 0.4353(8) 0.8181(9) 0.1274(6) 0.026(2) Uani 1 1 d . . .
H2A H 0.4001 0.9126 0.1031 0.039 Uiso 1 1 calc R . .
H2B H 0.5360 0.8042 0.1018 0.039 Uiso 1 1 calc R . .
H2C H 0.4362 0.8013 0.1948 0.039 Uiso 1 1 calc R . .
N3 N 0.1710(6) 0.6977(7) -0.0074(4) 0.0178(15) Uani 1 1 d . . .
C3 C 0.3892(9) 0.5774(8) 0.1245(6) 0.029(2) Uani 1 1 d . . .
H3A H 0.3101 0.5173 0.1168 0.043 Uiso 1 1 calc R . .
H3B H 0.4183 0.5544 0.1886 0.043 Uiso 1 1 calc R . .
H3C H 0.4754 0.5645 0.0834 0.043 Uiso 1 1 calc R . .
N4 N -0.1196(7) 0.9795(6) 0.1211(4) 0.0165(14) Uani 1 1 d . . .
C4 C 0.2769(9) 0.6371(9) -0.0650(6) 0.031(2) Uani 1 1 d . . .
H4A H 0.3748 0.6751 -0.0638 0.046 Uiso 1 1 calc R . .
H4B H 0.2447 0.6577 -0.1285 0.046 Uiso 1 1 calc R . .
H4C H 0.2828 0.5374 -0.0419 0.046 Uiso 1 1 calc R . .
N5 N 0.1736(6) 0.3790(6) 0.4811(4) 0.0142(14) Uani 1 1 d . . .
C5 C 0.0177(9) 0.7020(9) -0.0339(6) 0.026(2) Uani 1 1 d . . .
H5A H -0.0483 0.7322 0.0132 0.038 Uiso 1 1 calc R . .
H5B H -0.0092 0.6102 -0.0393 0.038 Uiso 1 1 calc R . .
H5C H 0.0074 0.7665 -0.0933 0.038 Uiso 1 1 calc R . .
N6 N 0.3452(7) 0.2593(7) 0.3994(4) 0.0192(15) Uani 1 1 d . . .
C6 C 0.1239(7) 0.8952(8) 0.1686(5) 0.0162(17) Uani 1 1 d . . .
H6A H 0.1881 0.9723 0.1704 0.019 Uiso 1 1 calc R . .
H6B H 0.1595 0.8128 0.2130 0.019 Uiso 1 1 calc R . .
N7 N 0.0919(7) 0.2328(7) 0.3948(5) 0.0244(16) Uani 1 1 d . . .
C7 C -0.0354(8) 0.9306(8) 0.1934(5) 0.0165(17) Uani 1 1 d . . .
C8 C -0.0951(9) 0.9127(8) 0.2833(5) 0.0216(19) Uani 1 1 d . . .
H8A H -0.0352 0.8767 0.3340 0.026 Uiso 1 1 calc R . .
N8 N 0.0675(7) 0.4535(7) 0.6285(4) 0.0177(15) Uani 1 1 d . . .
C9 C -0.2436(10) 0.9483(9) 0.2978(6) 0.029(2) Uani 1 1 d . . .
H9A H -0.2859 0.9395 0.3588 0.035 Uiso 1 1 calc R . .
C10 C -0.3285(9) 0.9960(9) 0.2240(6) 0.028(2) Uani 1 1 d . . .
H10A H -0.4313 1.0177 0.2327 0.033 Uiso 1 1 calc R . .
C11 C -0.2629(9) 1.0119(8) 0.1368(6) 0.0243(19) Uani 1 1 d . . .
H11A H -0.3217 1.0475 0.0855 0.029 Uiso 1 1 calc R . .
C12 C 0.2034(8) 0.2934(8) 0.4269(5) 0.0157(17) Uani 1 1 d . . .
C13 C 0.3859(11) 0.1213(10) 0.3886(8) 0.049(3) Uani 1 1 d . . .
H13A H 0.3058 0.0595 0.4155 0.074 Uiso 1 1 calc R . .
H13B H 0.4775 0.0900 0.4202 0.074 Uiso 1 1 calc R . .
H13C H 0.4019 0.1212 0.3229 0.074 Uiso 1 1 calc R . .
C14 C 0.4604(8) 0.3588(9) 0.3769(6) 0.026(2) Uani 1 1 d . . .
H14A H 0.4179 0.4502 0.3790 0.040 Uiso 1 1 calc R . .
H14B H 0.5036 0.3593 0.3147 0.040 Uiso 1 1 calc R . .
H14C H 0.5381 0.3343 0.4215 0.040 Uiso 1 1 calc R . .
C15 C 0.1038(11) 0.2013(10) 0.3029(6) 0.040(3) Uani 1 1 d . . .
H15A H 0.1827 0.2549 0.2654 0.060 Uiso 1 1 calc R . .
H15B H 0.0090 0.2248 0.2732 0.060 Uiso 1 1 calc R . .
H15C H 0.1274 0.1031 0.3085 0.060 Uiso 1 1 calc R . .
C16 C -0.0486(9) 0.2090(9) 0.4436(6) 0.029(2) Uani 1 1 d . . .
H16C H -0.0436 0.2284 0.5052 0.043 Uiso 1 1 calc R . .
H16B H -0.0740 0.1129 0.4495 0.043 Uiso 1 1 calc R . .
H16A H -0.1249 0.2692 0.4098 0.043 Uiso 1 1 calc R . .
C17 C 0.2883(8) 0.3988(8) 0.5437(5) 0.0186(18) Uani 1 1 d . . .
H17B H 0.3437 0.4827 0.5167 0.022 Uiso 1 1 calc R . .
H17A H 0.3597 0.3192 0.5537 0.022 Uiso 1 1 calc R . .
C18 C 0.2101(8) 0.4118(8) 0.6328(5) 0.0147(17) Uani 1 1 d . . .
C19 C 0.2802(8) 0.3817(8) 0.7158(5) 0.0167(17) Uani 1 1 d . . .
H19 H 0.3823 0.3540 0.7176 0.020 Uiso 1 1 calc R . .
C20 C 0.1988(9) 0.3927(8) 0.7955(5) 0.0228(19) Uani 1 1 d . . .
H20 H 0.2448 0.3740 0.8529 0.027 Uiso 1 1 calc R . .
C21 C 0.0489(8) 0.4315(8) 0.7912(5) 0.0215(18) Uani 1 1 d . . .
H21 H -0.0089 0.4379 0.8457 0.026 Uiso 1 1 calc R . .
C22 C -0.0142(8) 0.4602(8) 0.7075(5) 0.0183(18) Uani 1 1 d . . .
H22 H -0.1170 0.4854 0.7044 0.022 Uiso 1 1 calc R . .


_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 1.928(6) 2_575 ?
Cu1 N1 1.928(6) . ?
Cu1 N4 2.018(6) 2_575 ?
Cu1 N4 2.018(6) . ?
N1 C1 1.316(9) . ?
N1 C6 1.461(9) . ?
C1 N2 1.344(9) . ?
C1 N3 1.349(9) . ?
Cu2 N5 1.978(6) 2_566 ?
Cu2 N5 1.978(6) . ?
Cu2 N8 1.992(6) 2_566 ?
Cu2 N8 1.992(6) . ?
N2 C3 1.474(10) . ?
N2 C2 1.476(9) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N3 C4 1.445(10) . ?
N3 C5 1.456(9) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
N4 C11 1.338(10) . ?
N4 C7 1.344(9) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N5 C12 1.307(9) . ?
N5 C17 1.480(8) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
N6 C12 1.369(9) . ?
N6 C14 1.443(10) . ?
N6 C13 1.450(11) . ?
C6 C7 1.507(10) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
N7 C12 1.357(9) . ?
N7 C16 1.425(10) . ?
N7 C15 1.466(10) . ?
C7 C8 1.388(11) . ?
C8 C9 1.386(11) . ?
C8 H8A 0.9500 . ?
N8 C18 1.334(9) . ?
N8 C22 1.362(10) . ?
C9 C10 1.364(12) . ?
C9 H9A 0.9500 . ?
C10 C11 1.372(11) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16C 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16A 0.9800 . ?
C17 C18 1.492(10) . ?
C17 H17B 0.9900 . ?
C17 H17A 0.9900 . ?
C18 C19 1.388(10) . ?
C19 C20 1.378(11) . ?
C19 H19 0.9500 . ?
C20 C21 1.390(11) . ?
C20 H20 0.9500 . ?
C21 C22 1.367(10) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

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 180.0(3) 2_575 . ?
N1 Cu1 N4 81.5(2) 2_575 2_575 ?
N1 Cu1 N4 98.5(2) . 2_575 ?
N1 Cu1 N4 98.5(2) 2_575 . ?
N1 Cu1 N4 81.5(2) . . ?
N4 Cu1 N4 180.0(3) 2_575 . ?
C1 N1 C6 119.9(6) . . ?
C1 N1 Cu1 130.7(5) . . ?
C6 N1 Cu1 109.3(5) . . ?
N1 C1 N2 120.6(7) . . ?
N1 C1 N3 121.1(6) . . ?
N2 C1 N3 118.3(7) . . ?
N5 Cu2 N5 179.997(1) 2_566 . ?
N5 Cu2 N8 81.2(2) 2_566 2_566 ?
N5 Cu2 N8 98.8(2) . 2_566 ?
N5 Cu2 N8 98.8(2) 2_566 . ?
N5 Cu2 N8 81.2(2) . . ?
N8 Cu2 N8 180.00(13) 2_566 . ?
C1 N2 C3 124.3(6) . . ?
C1 N2 C2 122.2(6) . . ?
C3 N2 C2 113.5(6) . . ?
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 123.4(6) . . ?
C1 N3 C5 121.2(6) . . ?
C4 N3 C5 114.6(6) . . ?
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 . . ?
C11 N4 C7 118.9(7) . . ?
C11 N4 Cu1 129.2(5) . . ?
C7 N4 Cu1 111.8(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 . . ?
C12 N5 C17 118.5(6) . . ?
C12 N5 Cu2 133.8(5) . . ?
C17 N5 Cu2 107.7(4) . . ?
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 . . ?
C12 N6 C14 122.2(6) . . ?
C12 N6 C13 121.3(7) . . ?
C14 N6 C13 116.4(7) . . ?
N1 C6 C7 107.5(5) . . ?
N1 C6 H6A 110.2 . . ?
C7 C6 H6A 110.2 . . ?
N1 C6 H6B 110.2 . . ?
C7 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
C12 N7 C16 122.5(7) . . ?
C12 N7 C15 121.5(7) . . ?
C16 N7 C15 115.7(6) . . ?
N4 C7 C8 121.1(7) . . ?
N4 C7 C6 114.9(6) . . ?
C8 C7 C6 123.9(7) . . ?
C9 C8 C7 118.9(7) . . ?
C9 C8 H8A 120.6 . . ?
C7 C8 H8A 120.6 . . ?
C18 N8 C22 119.7(6) . . ?
C18 N8 Cu2 112.8(5) . . ?
C22 N8 Cu2 127.5(5) . . ?
C10 C9 C8 119.5(8) . . ?
C10 C9 H9A 120.3 . . ?
C8 C9 H9A 120.3 . . ?
C9 C10 C11 118.9(8) . . ?
C9 C10 H10A 120.6 . . ?
C11 C10 H10A 120.6 . . ?
N4 C11 C10 122.7(8) . . ?
N4 C11 H11A 118.7 . . ?
C10 C11 H11A 118.7 . . ?
N5 C12 N7 120.4(6) . . ?
N5 C12 N6 123.1(6) . . ?
N7 C12 N6 116.4(7) . . ?
N6 C13 H13A 109.5 . . ?
N6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N6 C14 H14A 109.5 . . ?
N6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N7 C15 H15A 109.5 . . ?
N7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N7 C16 H16C 109.5 . . ?
N7 C16 H16B 109.5 . . ?
H16C C16 H16B 109.5 . . ?
N7 C16 H16A 109.5 . . ?
H16C C16 H16A 109.5 . . ?
H16B C16 H16A 109.5 . . ?
N5 C17 C18 107.3(6) . . ?
N5 C17 H17B 110.3 . . ?
C18 C17 H17B 110.3 . . ?
N5 C17 H17A 110.3 . . ?
C18 C17 H17A 110.3 . . ?
H17B C17 H17A 108.5 . . ?
N8 C18 C19 121.5(7) . . ?
N8 C18 C17 116.1(6) . . ?
C19 C18 C17 122.4(6) . . ?
C20 C19 C18 118.8(7) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C19 C20 C21 119.5(7) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C22 C21 C20 119.2(7) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
N8 C22 C21 121.2(7) . . ?
N8 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?

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
N4 Cu1 N1 C1 -36.5(7) 2_575 . . . ?
N4 Cu1 N1 C1 143.5(7) . . . . ?
N4 Cu1 N1 C6 145.9(4) 2_575 . . . ?
N4 Cu1 N1 C6 -34.1(4) . . . . ?
C6 N1 C1 N2 -30.4(10) . . . . ?
Cu1 N1 C1 N2 152.2(6) . . . . ?
C6 N1 C1 N3 149.0(7) . . . . ?
Cu1 N1 C1 N3 -28.5(11) . . . . ?
N1 C1 N2 C3 146.3(8) . . . . ?
N3 C1 N2 C3 -33.1(11) . . . . ?
N1 C1 N2 C2 -37.1(11) . . . . ?
N3 C1 N2 C2 143.6(7) . . . . ?
N1 C1 N3 C4 147.3(8) . . . . ?
N2 C1 N3 C4 -33.3(11) . . . . ?
N1 C1 N3 C5 -22.0(11) . . . . ?
N2 C1 N3 C5 157.3(7) . . . . ?
N1 Cu1 N4 C11 18.4(7) 2_575 . . . ?
N1 Cu1 N4 C11 -161.6(7) . . . . ?
N1 Cu1 N4 C7 -158.9(5) 2_575 . . . ?
N1 Cu1 N4 C7 21.1(5) . . . . ?
N8 Cu2 N5 C12 -32.8(8) 2_566 . . . ?
N8 Cu2 N5 C12 147.2(8) . . . . ?
N8 Cu2 N5 C17 146.2(5) 2_566 . . . ?
N8 Cu2 N5 C17 -33.8(5) . . . . ?
C1 N1 C6 C7 -137.8(7) . . . . ?
Cu1 N1 C6 C7 40.2(7) . . . . ?
C11 N4 C7 C8 0.4(11) . . . . ?
Cu1 N4 C7 C8 178.0(6) . . . . ?
C11 N4 C7 C6 179.1(7) . . . . ?
Cu1 N4 C7 C6 -3.2(8) . . . . ?
N1 C6 C7 N4 -23.6(9) . . . . ?
N1 C6 C7 C8 155.1(7) . . . . ?
N4 C7 C8 C9 -1.0(11) . . . . ?
C6 C7 C8 C9 -179.6(7) . . . . ?
N5 Cu2 N8 C18 -158.3(5) 2_566 . . . ?
N5 Cu2 N8 C18 21.7(5) . . . . ?
N5 Cu2 N8 C22 21.7(7) 2_566 . . . ?
N5 Cu2 N8 C22 -158.3(7) . . . . ?
C7 C8 C9 C10 1.9(12) . . . . ?
C8 C9 C10 C11 -2.2(12) . . . . ?
C7 N4 C11 C10 -0.8(12) . . . . ?
Cu1 N4 C11 C10 -177.9(6) . . . . ?
C9 C10 C11 N4 1.7(13) . . . . ?
C17 N5 C12 N7 155.4(7) . . . . ?
Cu2 N5 C12 N7 -25.7(12) . . . . ?
C17 N5 C12 N6 -24.4(11) . . . . ?
Cu2 N5 C12 N6 154.4(6) . . . . ?
C16 N7 C12 N5 -27.2(12) . . . . ?
C15 N7 C12 N5 146.1(8) . . . . ?
C16 N7 C12 N6 152.6(8) . . . . ?
C15 N7 C12 N6 -34.0(11) . . . . ?
C14 N6 C12 N5 -38.6(11) . . . . ?
C13 N6 C12 N5 143.5(9) . . . . ?
C14 N6 C12 N7 141.5(7) . . . . ?
C13 N6 C12 N7 -36.4(11) . . . . ?
C12 N5 C17 C18 -141.5(7) . . . . ?
Cu2 N5 C17 C18 39.4(7) . . . . ?
C22 N8 C18 C19 -3.4(11) . . . . ?
Cu2 N8 C18 C19 176.5(6) . . . . ?
C22 N8 C18 C17 176.1(7) . . . . ?
Cu2 N8 C18 C17 -3.9(8) . . . . ?
N5 C17 C18 N8 -23.6(9) . . . . ?
N5 C17 C18 C19 155.9(7) . . . . ?
N8 C18 C19 C20 1.3(12) . . . . ?
C17 C18 C19 C20 -178.2(7) . . . . ?
C18 C19 C20 C21 1.0(12) . . . . ?
C19 C20 C21 C22 -1.1(12) . . . . ?
C18 N8 C22 C21 3.2(11) . . . . ?
Cu2 N8 C22 C21 -176.7(6) . . . . ?
C20 C21 C22 N8 -1.0(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.378
_refine_diff_density_min         -0.699
_refine_diff_density_rms         0.145
####################################################################### 
# 
# 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 2118640'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-07-28 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         'C26 H42 Br Cu N10, Br [+ pentane] '
_chemical_formula_sum            'C26 H42 Br2 Cu N10 [+ pentane] '
_chemical_formula_weight         718.05

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/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                   12.868(3)
_cell_length_b                   21.016(4)
_cell_length_c                   13.142(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.75(3)
_cell_angle_gamma                90
_cell_volume                     3541.9(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7006
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      30.33
_exptl_crystal_description       plate
_exptl_crystal_colour            blue

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             1468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.903
_shelx_estimated_absorpt_T_min   0.623
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5663
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS-2008/1
_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  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51931
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.832
_diffrn_reflns_theta_max         30.504
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10461
_reflns_number_gt                6428
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0478P)²+17.7599P] 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         10461
_refine_ls_number_parameters     360
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1230
_refine_ls_R_factor_gt           0.0737
_refine_ls_wR_factor_ref         0.1757
_refine_ls_wR_factor_gt          0.1509
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.42814(5) 0.64501(3) 0.35906(5) 0.02478(14) Uani 1 1 d . . . . .
Br1 Br 0.42763(4) 0.78159(3) 0.36023(4) 0.03103(13) Uani 1 1 d . . . . .
N1 N 0.3501(3) 0.6208(2) 0.4815(3) 0.0230(9) Uani 1 1 d . . . . .
C1 C 0.2660(4) 0.5878(3) 0.4936(4) 0.0282(11) Uani 1 1 d . . . . .
N2 N 0.2334(4) 0.5400(2) 0.4281(4) 0.0363(11) Uani 1 1 d . . . . .
Br2 Br -0.07557(5) 0.64580(4) 0.35805(5) 0.04476(17) Uani 1 1 d . . . . .
C2 C 0.1723(5) 0.6540(4) 0.6127(5) 0.0477(17) Uani 1 1 d . . . . .
H2A H 0.137962 0.680605 0.558713 0.071 Uiso 1 1 calc R U . . .
H2B H 0.235609 0.675259 0.641967 0.071 Uiso 1 1 calc R U . . .
H2C H 0.124761 0.647153 0.666275 0.071 Uiso 1 1 calc R U . . .
N3 N 0.1996(3) 0.5931(2) 0.5702(3) 0.0321(10) Uani 1 1 d . . . . .
C3 C 0.3040(5) 0.5054(3) 0.3685(5) 0.0458(16) Uani 1 1 d . . . . .
H3A H 0.264843 0.473700 0.326156 0.069 Uiso 1 1 calc R U . . .
H3B H 0.356751 0.483885 0.414350 0.069 Uiso 1 1 calc R U . . .
H3C H 0.338312 0.535069 0.324508 0.069 Uiso 1 1 calc R U . . .
N4 N 0.5463(3) 0.6508(2) 0.4666(3) 0.0264(9) Uani 1 1 d . . . . .
C4 C 0.1519(5) 0.5022(4) 0.4728(5) 0.0507(18) Uani 1 1 d . . . . .
H4A H 0.181665 0.464456 0.509565 0.061 Uiso 1 1 calc R U . . .
H4AB H 0.097209 0.488404 0.419969 0.061 Uiso 1 1 calc R U . . .
C5 C 0.1101(4) 0.5498(4) 0.5451(5) 0.0472(17) Uani 1 1 d . . . . .
H5A H 0.049777 0.573183 0.511929 0.057 Uiso 1 1 calc R U . . .
H5AB H 0.088677 0.528471 0.607245 0.057 Uiso 1 1 calc R U . . .
N5 N 0.7625(3) 0.6763(3) 0.7196(4) 0.0398(13) Uani 1 1 d . . . . .
N6 N 0.5075(3) 0.6298(2) 0.2347(3) 0.0250(9) Uani 1 1 d . . . . .
C6 C 0.5155(4) 0.6560(2) 0.5619(4) 0.0224(10) Uani 1 1 d . . . . .
C7 C 0.5838(4) 0.6634(2) 0.6480(4) 0.0231(10) Uani 1 1 d . . . . .
H7 H 0.558115 0.665632 0.713671 0.028 Uiso 1 1 calc R U . . .
N7 N 0.6334(4) 0.5511(2) 0.2763(3) 0.0310(10) Uani 1 1 d . . . . .
N8 N 0.6572(3) 0.6118(2) 0.1405(3) 0.0300(10) Uani 1 1 d . . . . .
C8 C 0.6920(4) 0.6676(3) 0.6377(4) 0.0241(10) Uani 1 1 d . . . . .
C9 C 0.7234(4) 0.6636(3) 0.5369(4) 0.0274(11) Uani 1 1 d . . . . .
H9 H 0.795071 0.666124 0.524981 0.033 Uiso 1 1 calc R U . . .
N9 N 0.3097(3) 0.6530(2) 0.2531(3) 0.0241(9) Uani 1 1 d . . . . .
C13 C 0.3994(4) 0.6560(3) 0.5694(4) 0.0258(11) Uani 1 1 d . . . . .
H13A H 0.382766 0.635369 0.633843 0.031 Uiso 1 1 calc R U . . .
H13B H 0.372890 0.700207 0.569120 0.031 Uiso 1 1 calc R U . . .
C12 C 0.7315(5) 0.6906(4) 0.8216(4) 0.0503(18) Uani 1 1 d . . . . .
H12A H 0.659623 0.706497 0.816326 0.075 Uiso 1 1 calc R U . . .
H12B H 0.778069 0.723023 0.853693 0.075 Uiso 1 1 calc R U . . .
H12C H 0.735843 0.651820 0.863141 0.075 Uiso 1 1 calc R U . . .
C11 C 0.8750(4) 0.6762(4) 0.7112(5) 0.0506(18) Uani 1 1 d . . . . .
H11A H 0.889988 0.655888 0.646871 0.076 Uiso 1 1 calc R U . . .
H11B H 0.909622 0.652533 0.768599 0.076 Uiso 1 1 calc R U . . .
H11C H 0.900769 0.720093 0.712368 0.076 Uiso 1 1 calc R U . . .
C10 C 0.6489(4) 0.6561(3) 0.4567(4) 0.0287(11) Uani 1 1 d . . . . .
H10 H 0.671558 0.654615 0.389753 0.034 Uiso 1 1 calc R U . . .
N10 N 0.0921(3) 0.6964(3) 0.0076(3) 0.0363(12) Uani 1 1 d . . . . .
C14 C 0.5936(4) 0.6007(3) 0.2171(4) 0.0277(11) Uani 1 1 d . . . . .
C15 C 0.5690(5) 0.5113(3) 0.3359(5) 0.0402(14) Uani 1 1 d . . . . .
H15A H 0.518971 0.487698 0.289896 0.060 Uiso 1 1 calc R U . . .
H15B H 0.531127 0.538065 0.381439 0.060 Uiso 1 1 calc R U . . .
H15C H 0.613296 0.481207 0.376589 0.060 Uiso 1 1 calc R U . . .
C16 C 0.6761(5) 0.6754(3) 0.1019(5) 0.0402(15) Uani 1 1 d . . . . .
H16A H 0.747524 0.678020 0.081502 0.060 Uiso 1 1 calc R U . . .
H16B H 0.666792 0.706806 0.155602 0.060 Uiso 1 1 calc R U . . .
H16C H 0.626730 0.684251 0.042814 0.060 Uiso 1 1 calc R U . . .
C17 C 0.7502(4) 0.5706(3) 0.1533(4) 0.0402(15) Uani 1 1 d . . . . .
H17A H 0.812733 0.595385 0.177876 0.048 Uiso 1 1 calc R U . . .
H17B H 0.763270 0.549543 0.088180 0.048 Uiso 1 1 calc R U . . .
C18 C 0.7224(5) 0.5220(3) 0.2328(5) 0.0431(15) Uani 1 1 d . . . . .
H18A H 0.703296 0.480591 0.200645 0.052 Uiso 1 1 calc R U . . .
H18B H 0.781017 0.515680 0.285445 0.052 Uiso 1 1 calc R U . . .
C19 C 0.3397(4) 0.6659(2) 0.1593(3) 0.0221(10) Uani 1 1 d . . . . .
C20 C 0.2703(4) 0.6791(3) 0.0769(4) 0.0279(11) Uani 1 1 d . . . . .
H20 H 0.295439 0.686985 0.012191 0.034 Uiso 1 1 calc R U . . .
C22 C 0.1312(4) 0.6677(3) 0.1861(4) 0.0266(11) Uani 1 1 d . . . . .
H22 H 0.059498 0.667521 0.198388 0.032 Uiso 1 1 calc R U . . .
C21 C 0.1617(4) 0.6810(3) 0.0873(4) 0.0280(11) Uani 1 1 d . . . . .
C23 C 0.2062(4) 0.6550(3) 0.2641(4) 0.0276(11) Uani 1 1 d . . . . .
H23 H 0.183799 0.647067 0.330018 0.033 Uiso 1 1 calc R U . . .
C24 C 0.1256(5) 0.7106(4) -0.0920(4) 0.055(2) Uani 1 1 d . . . . .
H24A H 0.146070 0.671132 -0.124610 0.082 Uiso 1 1 calc R U . . .
H24B H 0.185226 0.739715 -0.084833 0.082 Uiso 1 1 calc R U . . .
H24C H 0.068215 0.730611 -0.134055 0.082 Uiso 1 1 calc R U . . .
C25 C -0.0200(4) 0.6938(4) 0.0172(4) 0.0424(16) Uani 1 1 d . . . . .
H25A H -0.055414 0.724714 -0.029473 0.064 Uiso 1 1 calc R U . . .
H25B H -0.034001 0.703888 0.087514 0.064 Uiso 1 1 calc R U . . .
H25C H -0.045810 0.650918 -0.000163 0.064 Uiso 1 1 calc R U . . .
C26 C 0.4559(4) 0.6688(3) 0.1519(3) 0.0249(10) Uani 1 1 d . . . . .
H26A H 0.473265 0.652206 0.084800 0.030 Uiso 1 1 calc R U . . .
H26B H 0.480389 0.713345 0.158292 0.030 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 N9 1.985(4) . ?
Cu1 N4 1.992(4) . ?
Cu1 N6 2.023(4) . ?
Cu1 N1 2.031(4) . ?
Cu1 Br1 2.8704(10) . ?
N1 C1 1.307(6) . ?
N1 C13 1.470(6) . ?
C1 N2 1.365(7) . ?
C1 N3 1.377(7) . ?
N2 C3 1.444(8) . ?
N2 C4 1.476(7) . ?
C2 N3 1.452(8) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N3 C5 1.483(7) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
N4 C10 1.343(6) . ?
N4 C6 1.348(6) . ?
C4 C5 1.508(10) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
N5 C8 1.362(6) . ?
N5 C11 1.460(7) . ?
N5 C12 1.462(7) . ?
N6 C14 1.304(6) . ?
N6 C26 1.475(6) . ?
C6 C7 1.384(6) . ?
C6 C13 1.505(6) . ?
C7 C8 1.413(7) . ?
C7 H7 0.9500 . ?
N7 C14 1.374(7) . ?
N7 C15 1.452(7) . ?
N7 C18 1.456(7) . ?
N8 C14 1.369(7) . ?
N8 C16 1.458(8) . ?
N8 C17 1.475(7) . ?
C8 C9 1.419(7) . ?
C9 C10 1.373(7) . ?
C9 H9 0.9500 . ?
N9 C19 1.348(6) . ?
N9 C23 1.353(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C10 H10 0.9500 . ?
N10 C21 1.359(6) . ?
N10 C24 1.443(7) . ?
N10 C25 1.459(7) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.525(9) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.374(7) . ?
C19 C26 1.508(6) . ?
C20 C21 1.416(7) . ?
C20 H20 0.9500 . ?
C22 C23 1.374(7) . ?
C22 C21 1.415(7) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
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 0.9900 . ?
C26 H26B 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
N9 Cu1 N4 171.64(18) . . ?
N9 Cu1 N6 81.73(17) . . ?
N4 Cu1 N6 100.14(16) . . ?
N9 Cu1 N1 100.16(16) . . ?
N4 Cu1 N1 81.43(16) . . ?
N6 Cu1 N1 156.43(18) . . ?
N9 Cu1 Br1 85.25(13) . . ?
N4 Cu1 Br1 86.40(14) . . ?
N6 Cu1 Br1 99.42(13) . . ?
N1 Cu1 Br1 104.15(13) . . ?
C1 N1 C13 118.7(4) . . ?
C1 N1 Cu1 134.2(3) . . ?
C13 N1 Cu1 106.7(3) . . ?
N1 C1 N2 121.9(5) . . ?
N1 C1 N3 128.0(5) . . ?
N2 C1 N3 110.1(5) . . ?
C1 N2 C3 122.6(5) . . ?
C1 N2 C4 109.6(5) . . ?
C3 N2 C4 116.4(5) . . ?
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 N3 C2 122.5(5) . . ?
C1 N3 C5 107.8(5) . . ?
C2 N3 C5 114.7(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 . . ?
C10 N4 C6 116.8(4) . . ?
C10 N4 Cu1 129.4(3) . . ?
C6 N4 Cu1 113.4(3) . . ?
N2 C4 C5 101.3(5) . . ?
N2 C4 H4A 111.5 . . ?
C5 C4 H4A 111.5 . . ?
N2 C4 H4AB 111.5 . . ?
C5 C4 H4AB 111.5 . . ?
H4A C4 H4AB 109.3 . . ?
N3 C5 C4 103.6(5) . . ?
N3 C5 H5A 111.0 . . ?
C4 C5 H5A 111.0 . . ?
N3 C5 H5AB 111.0 . . ?
C4 C5 H5AB 111.0 . . ?
H5A C5 H5AB 109.0 . . ?
C8 N5 C11 122.7(5) . . ?
C8 N5 C12 122.5(5) . . ?
C11 N5 C12 114.7(5) . . ?
C14 N6 C26 117.8(4) . . ?
C14 N6 Cu1 135.4(4) . . ?
C26 N6 Cu1 106.4(3) . . ?
N4 C6 C7 123.6(4) . . ?
N4 C6 C13 115.5(4) . . ?
C7 C6 C13 120.8(4) . . ?
C6 C7 C8 119.5(4) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C14 N7 C15 122.7(5) . . ?
C14 N7 C18 111.3(4) . . ?
C15 N7 C18 118.3(5) . . ?
C14 N8 C16 122.7(5) . . ?
C14 N8 C17 110.2(4) . . ?
C16 N8 C17 114.9(5) . . ?
N5 C8 C7 122.0(4) . . ?
N5 C8 C9 121.6(5) . . ?
C7 C8 C9 116.4(4) . . ?
C10 C9 C8 119.3(5) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C19 N9 C23 116.8(4) . . ?
C19 N9 Cu1 113.4(3) . . ?
C23 N9 Cu1 129.3(3) . . ?
N1 C13 C6 108.3(4) . . ?
N1 C13 H13A 110.0 . . ?
C6 C13 H13A 110.0 . . ?
N1 C13 H13B 110.0 . . ?
C6 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
N5 C12 H12A 109.5 . . ?
N5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N5 C11 H11A 109.5 . . ?
N5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N4 C10 C9 124.4(5) . . ?
N4 C10 H10 117.8 . . ?
C9 C10 H10 117.8 . . ?
C21 N10 C24 121.4(5) . . ?
C21 N10 C25 121.2(4) . . ?
C24 N10 C25 117.2(4) . . ?
N6 C14 N8 128.3(5) . . ?
N6 C14 N7 122.5(5) . . ?
N8 C14 N7 109.2(5) . . ?
N7 C15 H15A 109.5 . . ?
N7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N8 C16 H16A 109.5 . . ?
N8 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N8 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N8 C17 C18 103.7(5) . . ?
N8 C17 H17A 111.0 . . ?
C18 C17 H17A 111.0 . . ?
N8 C17 H17B 111.0 . . ?
C18 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
N7 C18 C17 103.0(5) . . ?
N7 C18 H18A 111.2 . . ?
C17 C18 H18A 111.2 . . ?
N7 C18 H18B 111.2 . . ?
C17 C18 H18B 111.2 . . ?
H18A C18 H18B 109.1 . . ?
N9 C19 C20 122.9(4) . . ?
N9 C19 C26 115.3(4) . . ?
C20 C19 C26 121.7(4) . . ?
C19 C20 C21 120.9(5) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C23 C22 C21 119.5(5) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
N10 C21 C22 122.6(5) . . ?
N10 C21 C20 121.7(5) . . ?
C22 C21 C20 115.6(5) . . ?
N9 C23 C22 124.2(4) . . ?
N9 C23 H23 117.9 . . ?
C22 C23 H23 117.9 . . ?
N10 C24 H24A 109.5 . . ?
N10 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N10 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N10 C25 H25A 109.5 . . ?
N10 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N10 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N6 C26 C19 108.6(4) . . ?
N6 C26 H26A 110.0 . . ?
C19 C26 H26A 110.0 . . ?
N6 C26 H26B 110.0 . . ?
C19 C26 H26B 110.0 . . ?
H26A C26 H26B 108.4 . . ?

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
C13 N1 C1 N2 -160.3(5) . . . . ?
Cu1 N1 C1 N2 27.7(8) . . . . ?
C13 N1 C1 N3 18.2(8) . . . . ?
Cu1 N1 C1 N3 -153.8(4) . . . . ?
N1 C1 N2 C3 25.3(8) . . . . ?
N3 C1 N2 C3 -153.5(5) . . . . ?
N1 C1 N2 C4 167.3(5) . . . . ?
N3 C1 N2 C4 -11.5(7) . . . . ?
N1 C1 N3 C2 38.1(8) . . . . ?
N2 C1 N3 C2 -143.3(5) . . . . ?
N1 C1 N3 C5 174.5(5) . . . . ?
N2 C1 N3 C5 -6.8(6) . . . . ?
C1 N2 C4 C5 24.0(7) . . . . ?
C3 N2 C4 C5 168.6(5) . . . . ?
C1 N3 C5 C4 21.5(6) . . . . ?
C2 N3 C5 C4 161.8(5) . . . . ?
N2 C4 C5 N3 -26.5(6) . . . . ?
C10 N4 C6 C7 -3.2(8) . . . . ?
Cu1 N4 C6 C7 -177.2(4) . . . . ?
C10 N4 C6 C13 174.5(5) . . . . ?
Cu1 N4 C6 C13 0.5(6) . . . . ?
N4 C6 C7 C8 1.8(8) . . . . ?
C13 C6 C7 C8 -175.7(5) . . . . ?
C11 N5 C8 C7 175.5(6) . . . . ?
C12 N5 C8 C7 -8.5(9) . . . . ?
C11 N5 C8 C9 -5.9(9) . . . . ?
C12 N5 C8 C9 170.1(6) . . . . ?
C6 C7 C8 N5 178.5(5) . . . . ?
C6 C7 C8 C9 -0.2(8) . . . . ?
N5 C8 C9 C10 -178.6(6) . . . . ?
C7 C8 C9 C10 0.0(8) . . . . ?
C1 N1 C13 C6 146.4(5) . . . . ?
Cu1 N1 C13 C6 -39.5(5) . . . . ?
N4 C6 C13 N1 26.7(6) . . . . ?
C7 C6 C13 N1 -155.5(5) . . . . ?
C6 N4 C10 C9 3.0(8) . . . . ?
Cu1 N4 C10 C9 175.9(4) . . . . ?
C8 C9 C10 N4 -1.5(9) . . . . ?
C26 N6 C14 N8 16.4(8) . . . . ?
Cu1 N6 C14 N8 -154.7(4) . . . . ?
C26 N6 C14 N7 -162.6(5) . . . . ?
Cu1 N6 C14 N7 26.3(8) . . . . ?
C16 N8 C14 N6 36.0(8) . . . . ?
C17 N8 C14 N6 176.2(5) . . . . ?
C16 N8 C14 N7 -144.9(5) . . . . ?
C17 N8 C14 N7 -4.7(6) . . . . ?
C15 N7 C14 N6 24.1(8) . . . . ?
C18 N7 C14 N6 172.8(5) . . . . ?
C15 N7 C14 N8 -155.0(5) . . . . ?
C18 N7 C14 N8 -6.3(6) . . . . ?
C14 N8 C17 C18 13.0(6) . . . . ?
C16 N8 C17 C18 156.5(5) . . . . ?
C14 N7 C18 C17 14.0(7) . . . . ?
C15 N7 C18 C17 164.2(5) . . . . ?
N8 C17 C18 N7 -15.6(6) . . . . ?
C23 N9 C19 C20 -1.6(8) . . . . ?
Cu1 N9 C19 C20 -173.9(4) . . . . ?
C23 N9 C19 C26 175.0(5) . . . . ?
Cu1 N9 C19 C26 2.7(6) . . . . ?
N9 C19 C20 C21 1.3(8) . . . . ?
C26 C19 C20 C21 -175.1(5) . . . . ?
C24 N10 C21 C22 179.1(6) . . . . ?
C25 N10 C21 C22 -6.3(9) . . . . ?
C24 N10 C21 C20 0.9(9) . . . . ?
C25 N10 C21 C20 175.5(6) . . . . ?
C23 C22 C21 N10 -177.4(6) . . . . ?
C23 C22 C21 C20 0.9(8) . . . . ?
C19 C20 C21 N10 177.4(5) . . . . ?
C19 C20 C21 C22 -0.9(8) . . . . ?
C19 N9 C23 C22 1.6(8) . . . . ?
Cu1 N9 C23 C22 172.5(4) . . . . ?
C21 C22 C23 N9 -1.3(9) . . . . ?
C14 N6 C26 C19 147.4(5) . . . . ?
Cu1 N6 C26 C19 -39.1(5) . . . . ?
N9 C19 C26 N6 25.0(6) . . . . ?
C20 C19 C26 N6 -158.3(5) . . . . ?

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 H5A Br2 0.99 2.91 3.854(6) 159.4 . yes
C7 H7 Br1 0.95 2.88 3.752(5) 153.1 4_576 yes
C9 H9 Br2 0.95 2.89 3.656(5) 138.1 1_655 yes
C15 H15B N4 0.98 2.62 3.423(8) 139.2 . yes
C17 H17A Br2 0.99 2.87 3.710(7) 143.3 1_655 yes
C20 H20 Br1 0.95 2.81 3.722(5) 161.8 4_575 yes
C22 H22 Br2 0.95 2.87 3.660(5) 141.3 . yes

_refine_diff_density_max         1.124
_refine_diff_density_min         -0.760
_refine_diff_density_rms         0.126



####################################################################### 
# 
# 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 2118643'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-07-28 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         'C32 H42 Br Cu N10, Br [+ CH3CN]'
_chemical_formula_sum            'C32 H42 Br2 Cu N10 [+ CH3CN]'
_chemical_formula_weight         790.11

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      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                   11.840(2)
_cell_length_b                   12.829(3)
_cell_length_c                   13.614(3)
_cell_angle_alpha                64.90(3)
_cell_angle_beta                 88.44(3)
_cell_angle_gamma                73.15(3)
_cell_volume                     1781.3(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    22664
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      33.34

_exptl_crystal_description       rod
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_F_000             806
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.893
_shelx_estimated_absorpt_T_min   0.498
_shelx_estimated_absorpt_T_max   0.761
_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  0.3051
_exptl_absorpt_correction_T_max  0.6421
_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      
; 1225 frames, detector distance = 60 mm
;

_diffrn_reflns_number            26137
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.148
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             7747
_reflns_number_gt                5447
_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)+(0.0808P)²+0.7329P] 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         7747
_refine_ls_number_parameters     414
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1520
_refine_ls_wR_factor_gt          0.1360
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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 0.25345(5) 1.02898(4) 0.50020(4) 0.02520(15) Uani 1 1 d . . . . .
Cu1 Cu 0.30577(5) 0.79159(5) 0.54911(4) 0.01759(15) Uani 1 1 d . . . . .
N1 N 0.4215(3) 0.6997(3) 0.6896(3) 0.0188(8) Uani 1 1 d . . . . .
C1 C 0.5394(4) 0.6685(4) 0.6921(4) 0.0186(10) Uani 1 1 d . . . . .
Br2 Br 0.00218(5) 0.35167(5) 0.80224(4) 0.02756(15) Uani 1 1 d . . . . .
N2 N 0.5992(4) 0.5977(4) 0.6476(3) 0.0223(9) Uani 1 1 d . . . . .
C2 C 0.5494(5) 0.5336(5) 0.6040(4) 0.0301(12) Uani 1 1 d . . . . .
H2A H 0.606302 0.453640 0.622171 0.045 Uiso 1 1 calc R U . . .
H2B H 0.532583 0.579499 0.524560 0.045 Uiso 1 1 calc R U . . .
H2C H 0.475696 0.524201 0.635827 0.045 Uiso 1 1 calc R U . . .
N3 N 0.6142(4) 0.7069(4) 0.7326(3) 0.0218(9) Uani 1 1 d . . . . .
C3 C 0.5800(5) 0.8133(5) 0.7511(4) 0.0269(12) Uani 1 1 d . . . . .
H3A H 0.630171 0.864111 0.714187 0.040 Uiso 1 1 calc R U . . .
H3B H 0.589745 0.789858 0.829675 0.040 Uiso 1 1 calc R U . . .
H3C H 0.496717 0.858708 0.722226 0.040 Uiso 1 1 calc R U . . .
N4 N 0.1903(4) 0.7851(3) 0.6552(3) 0.0187(9) Uani 1 1 d . . . . .
C4 C 0.7232(5) 0.5938(5) 0.6443(5) 0.0309(12) Uani 1 1 d . . . . .
H4A H 0.739743 0.639893 0.568992 0.037 Uiso 1 1 calc R U . . .
H4B H 0.776594 0.509486 0.673420 0.037 Uiso 1 1 calc R U . . .
N5 N -0.0330(4) 0.8387(4) 0.8856(3) 0.0223(9) Uani 1 1 d . . . . .
C5 C 0.7372(4) 0.6534(5) 0.7176(4) 0.0261(11) Uani 1 1 d . . . . .
H5A H 0.783686 0.592762 0.788287 0.031 Uiso 1 1 calc R U . . .
H5B H 0.776675 0.716265 0.681826 0.031 Uiso 1 1 calc R U . . .
N6 N 0.2340(3) 0.7371(3) 0.4513(3) 0.0163(8) Uani 1 1 d . . . . .
C6 C 0.0732(4) 0.8219(4) 0.6358(3) 0.0166(10) Uani 1 1 d . . . . .
H6 H 0.039814 0.841614 0.565124 0.020 Uiso 1 1 calc R U . . .
N7 N 0.1219(4) 0.6099(3) 0.5511(3) 0.0199(9) Uani 1 1 d . . . . .
C7 C -0.0042(4) 0.8337(4) 0.7114(3) 0.0165(10) Uani 1 1 d . . . . .
H7 H -0.087436 0.855544 0.693737 0.020 Uiso 1 1 calc R U . . .
N8 N 0.0261(3) 0.7737(3) 0.4058(3) 0.0165(8) Uani 1 1 d . . . . .
C8 C 0.0412(4) 0.8133(4) 0.8140(4) 0.0182(10) Uani 1 1 d . . . . .
N9 N 0.4144(3) 0.8185(3) 0.4358(3) 0.0181(8) Uani 1 1 d . . . . .
C9 C 0.1673(4) 0.7630(4) 0.8418(4) 0.0179(10) Uani 1 1 d . . . . .
N10 N 0.6095(4) 0.9039(4) 0.1645(3) 0.0278(10) Uani 1 1 d . . . . .
C10 C 0.2241(5) 0.7129(4) 0.9489(4) 0.0207(11) Uani 1 1 d . . . . .
H10 H 0.178293 0.713345 1.007240 0.025 Uiso 1 1 calc R U . . .
C11 C 0.3449(5) 0.6640(4) 0.9687(4) 0.0243(11) Uani 1 1 d . . . . .
H11 H 0.381951 0.630921 1.040998 0.029 Uiso 1 1 calc R U . . .
C12 C 0.4155(5) 0.6614(5) 0.8847(4) 0.0229(11) Uani 1 1 d . . . . .
H12 H 0.499434 0.628709 0.900623 0.028 Uiso 1 1 calc R U . . .
C13 C 0.3646(4) 0.7056(4) 0.7799(4) 0.0182(10) Uani 1 1 d . . . . .
C14 C 0.2377(4) 0.7534(4) 0.7584(3) 0.0160(10) Uani 1 1 d . . . . .
C15 C -0.1591(4) 0.8617(5) 0.8650(4) 0.0300(12) Uani 1 1 d . . . . .
H15A H -0.196522 0.854375 0.931737 0.045 Uiso 1 1 calc R U . . .
H15B H -0.172124 0.802642 0.842312 0.045 Uiso 1 1 calc R U . . .
H15C H -0.194206 0.943506 0.806977 0.045 Uiso 1 1 calc R U . . .
C16 C -0.0047(5) 0.9014(4) 0.9461(4) 0.0243(11) Uani 1 1 d . . . . .
H16A H -0.006901 0.854431 1.024281 0.036 Uiso 1 1 calc R U . . .
H16B H -0.063277 0.981786 0.921060 0.036 Uiso 1 1 calc R U . . .
H16C H 0.074701 0.909707 0.933142 0.036 Uiso 1 1 calc R U . . .
C17 C 0.1316(4) 0.7094(4) 0.4653(3) 0.0158(10) Uani 1 1 d . . . . .
C18 C 0.2161(4) 0.5211(4) 0.6363(4) 0.0247(11) Uani 1 1 d . . . . .
H18A H 0.193842 0.447393 0.676130 0.037 Uiso 1 1 calc R U . . .
H18B H 0.228866 0.553939 0.686774 0.037 Uiso 1 1 calc R U . . .
H18C H 0.289417 0.502078 0.603495 0.037 Uiso 1 1 calc R U . . .
C19 C -0.0045(4) 0.8942(4) 0.3169(4) 0.0219(11) Uani 1 1 d . . . . .
H19A H -0.077405 0.945530 0.328930 0.033 Uiso 1 1 calc R U . . .
H19B H -0.017062 0.890048 0.247932 0.033 Uiso 1 1 calc R U . . .
H19C H 0.060251 0.928469 0.313634 0.033 Uiso 1 1 calc R U . . .
C20 C -0.0041(4) 0.6164(4) 0.5599(4) 0.0207(10) Uani 1 1 d . . . . .
H20A H -0.035175 0.642468 0.616861 0.025 Uiso 1 1 calc R U . . .
H20B H -0.015765 0.537528 0.576643 0.025 Uiso 1 1 calc R U . . .
C21 C -0.0628(4) 0.7107(4) 0.4472(4) 0.0198(10) Uani 1 1 d . . . . .
H21A H -0.077528 0.672596 0.401091 0.024 Uiso 1 1 calc R U . . .
H21B H -0.138687 0.766478 0.451218 0.024 Uiso 1 1 calc R U . . .
C22 C 0.5065(4) 0.8592(4) 0.4324(4) 0.0183(10) Uani 1 1 d . . . . .
H22 H 0.528155 0.869068 0.493879 0.022 Uiso 1 1 calc R U . . .
C24 C 0.5445(4) 0.8767(4) 0.2521(4) 0.0194(10) Uani 1 1 d . . . . .
C25 C 0.4390(4) 0.8412(4) 0.2491(4) 0.0177(10) Uani 1 1 d . . . . .
C26 C 0.3883(4) 0.8415(4) 0.1559(4) 0.0207(10) Uani 1 1 d . . . . .
H26 H 0.422303 0.867349 0.089040 0.025 Uiso 1 1 calc R U . . .
C27 C 0.2897(4) 0.8043(4) 0.1630(4) 0.0221(11) Uani 1 1 d . . . . .
H27 H 0.257238 0.804093 0.100077 0.027 Uiso 1 1 calc R U . . .
C28 C 0.2348(4) 0.7667(4) 0.2584(4) 0.0202(10) Uani 1 1 d . . . . .
H28 H 0.169594 0.736804 0.261340 0.024 Uiso 1 1 calc R U . . .
C29 C 0.2771(4) 0.7736(4) 0.3493(4) 0.0166(10) Uani 1 1 d . . . . .
C30 C 0.3797(4) 0.8119(4) 0.3437(3) 0.0147(9) Uani 1 1 d . . . . .
C31 C 0.6976(5) 0.9639(6) 0.1631(4) 0.0367(15) Uani 1 1 d . . . . .
H31A H 0.723157 0.995365 0.089863 0.055 Uiso 1 1 calc R U . . .
H31B H 0.766313 0.905810 0.215920 0.055 Uiso 1 1 calc R U . . .
H31C H 0.662537 1.030935 0.182456 0.055 Uiso 1 1 calc R U . . .
C32 C 0.5728(4) 0.8880(4) 0.3448(4) 0.0191(10) Uani 1 1 d . . . . .
H32 H 0.638208 0.915649 0.348169 0.023 Uiso 1 1 calc R U . . .
C33 C 0.6444(5) 0.8219(6) 0.1115(4) 0.0361(14) Uani 1 1 d . . . . .
H33A H 0.621978 0.868364 0.032557 0.054 Uiso 1 1 calc R U . . .
H33B H 0.603966 0.760046 0.140617 0.054 Uiso 1 1 calc R U . . .
H33C H 0.730547 0.782924 0.125967 0.054 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 2.7039(11) . ?
Cu1 N4 1.954(4) . ?
Cu1 N9 1.961(4) . ?
Cu1 N6 2.045(4) . ?
Cu1 N1 2.054(4) . ?
N1 C1 1.333(6) . ?
N1 C13 1.406(6) . ?
C1 N2 1.327(6) . ?
C1 N3 1.358(6) . ?
N2 C2 1.446(6) . ?
N2 C4 1.455(6) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N3 C3 1.434(6) . ?
N3 C5 1.469(6) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
N4 C6 1.322(6) . ?
N4 C14 1.371(5) . ?
C4 C5 1.528(7) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
N5 C8 1.372(6) . ?
N5 C15 1.447(6) . ?
N5 C16 1.473(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
N6 C17 1.345(6) . ?
N6 C29 1.399(5) . ?
C6 C7 1.388(6) . ?
C6 H6 0.9500 . ?
N7 C17 1.349(5) . ?
N7 C18 1.449(6) . ?
N7 C20 1.473(6) . ?
C7 C8 1.399(6) . ?
C7 H7 0.9500 . ?
N8 C17 1.337(6) . ?
N8 C19 1.449(6) . ?
N8 C21 1.467(6) . ?
C8 C9 1.432(7) . ?
N9 C22 1.331(6) . ?
N9 C30 1.374(5) . ?
C9 C10 1.415(6) . ?
C9 C14 1.417(6) . ?
N10 C24 1.375(6) . ?
N10 C31 1.460(6) . ?
N10 C33 1.475(7) . ?
C10 C11 1.367(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.404(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.373(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.434(7) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C32 1.385(6) . ?
C22 H22 0.9500 . ?
C24 C32 1.391(6) . ?
C24 C25 1.455(6) . ?
C25 C30 1.409(6) . ?
C25 C26 1.417(6) . ?
C26 C27 1.370(7) . ?
C26 H26 0.9500 . ?
C27 C28 1.394(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.393(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.426(6) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 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
N4 Cu1 N9 173.38(16) . . ?
N4 Cu1 N6 101.10(15) . . ?
N9 Cu1 N6 81.04(15) . . ?
N4 Cu1 N1 81.22(16) . . ?
N9 Cu1 N1 101.97(16) . . ?
N6 Cu1 N1 133.11(15) . . ?
N4 Cu1 Br1 86.44(12) . . ?
N9 Cu1 Br1 87.10(12) . . ?
N6 Cu1 Br1 120.73(11) . . ?
N1 Cu1 Br1 106.16(11) . . ?
C1 N1 C13 121.6(4) . . ?
C1 N1 Cu1 124.4(3) . . ?
C13 N1 Cu1 111.5(3) . . ?
N2 C1 N1 122.4(4) . . ?
N2 C1 N3 110.5(4) . . ?
N1 C1 N3 127.0(4) . . ?
C1 N2 C2 125.4(4) . . ?
C1 N2 C4 111.9(4) . . ?
C2 N2 C4 122.6(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 . . ?
C1 N3 C3 125.1(4) . . ?
C1 N3 C5 110.0(4) . . ?
C3 N3 C5 121.6(4) . . ?
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 . . ?
C6 N4 C14 117.3(4) . . ?
C6 N4 Cu1 127.6(3) . . ?
C14 N4 Cu1 114.5(3) . . ?
N2 C4 C5 102.6(4) . . ?
N2 C4 H4A 111.2 . . ?
C5 C4 H4A 111.2 . . ?
N2 C4 H4B 111.2 . . ?
C5 C4 H4B 111.2 . . ?
H4A C4 H4B 109.2 . . ?
C8 N5 C15 119.2(4) . . ?
C8 N5 C16 120.7(4) . . ?
C15 N5 C16 113.2(4) . . ?
N3 C5 C4 103.4(4) . . ?
N3 C5 H5A 111.1 . . ?
C4 C5 H5A 111.1 . . ?
N3 C5 H5B 111.1 . . ?
C4 C5 H5B 111.1 . . ?
H5A C5 H5B 109.1 . . ?
C17 N6 C29 121.1(4) . . ?
C17 N6 Cu1 124.1(3) . . ?
C29 N6 Cu1 111.1(3) . . ?
N4 C6 C7 124.6(4) . . ?
N4 C6 H6 117.7 . . ?
C7 C6 H6 117.7 . . ?
C17 N7 C18 125.8(4) . . ?
C17 N7 C20 110.1(4) . . ?
C18 N7 C20 123.0(4) . . ?
C6 C7 C8 119.4(4) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C17 N8 C19 126.7(4) . . ?
C17 N8 C21 111.3(4) . . ?
C19 N8 C21 121.9(4) . . ?
N5 C8 C7 120.8(4) . . ?
N5 C8 C9 121.7(4) . . ?
C7 C8 C9 117.5(4) . . ?
C22 N9 C30 117.2(4) . . ?
C22 N9 Cu1 126.8(3) . . ?
C30 N9 Cu1 115.3(3) . . ?
C10 C9 C14 118.3(4) . . ?
C10 C9 C8 123.9(4) . . ?
C14 C9 C8 117.6(4) . . ?
C24 N10 C31 118.1(4) . . ?
C24 N10 C33 120.1(4) . . ?
C31 N10 C33 112.9(4) . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 121.6(4) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C13 C12 C11 120.7(5) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 N1 127.5(5) . . ?
C12 C13 C14 118.5(4) . . ?
N1 C13 C14 113.7(4) . . ?
N4 C14 C9 123.0(4) . . ?
N4 C14 C13 116.4(4) . . ?
C9 C14 C13 120.6(4) . . ?
N5 C15 H15A 109.5 . . ?
N5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N5 C16 H16A 109.5 . . ?
N5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N8 C17 N6 128.2(4) . . ?
N8 C17 N7 109.8(4) . . ?
N6 C17 N7 121.9(4) . . ?
N7 C18 H18A 109.5 . . ?
N7 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N7 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 . . ?
N7 C20 C21 102.4(4) . . ?
N7 C20 H20A 111.3 . . ?
C21 C20 H20A 111.3 . . ?
N7 C20 H20B 111.3 . . ?
C21 C20 H20B 111.3 . . ?
H20A C20 H20B 109.2 . . ?
N8 C21 C20 102.2(4) . . ?
N8 C21 H21A 111.3 . . ?
C20 C21 H21A 111.3 . . ?
N8 C21 H21B 111.3 . . ?
C20 C21 H21B 111.3 . . ?
H21A C21 H21B 109.2 . . ?
N9 C22 C32 124.1(4) . . ?
N9 C22 H22 118.0 . . ?
C32 C22 H22 118.0 . . ?
N10 C24 C32 121.6(4) . . ?
N10 C24 C25 121.2(4) . . ?
C32 C24 C25 117.1(4) . . ?
C30 C25 C26 118.1(4) . . ?
C30 C25 C24 117.3(4) . . ?
C26 C25 C24 124.5(4) . . ?
C27 C26 C25 119.5(4) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C26 C27 C28 123.0(4) . . ?
C26 C27 H27 118.5 . . ?
C28 C27 H27 118.5 . . ?
C29 C28 C27 119.1(4) . . ?
C29 C28 H28 120.5 . . ?
C27 C28 H28 120.5 . . ?
C28 C29 N6 126.1(4) . . ?
C28 C29 C30 118.7(4) . . ?
N6 C29 C30 115.0(4) . . ?
N9 C30 C25 123.6(4) . . ?
N9 C30 C29 115.1(4) . . ?
C25 C30 C29 121.3(4) . . ?
N10 C31 H31A 109.5 . . ?
N10 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N10 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C22 C32 C24 120.6(4) . . ?
C22 C32 H32 119.7 . . ?
C24 C32 H32 119.7 . . ?
N10 C33 H33A 109.5 . . ?
N10 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
N10 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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
C13 N1 C1 N2 140.2(5) . . . . ?
Cu1 N1 C1 N2 -59.5(6) . . . . ?
C13 N1 C1 N3 -43.7(7) . . . . ?
Cu1 N1 C1 N3 116.7(5) . . . . ?
N1 C1 N2 C2 -8.2(7) . . . . ?
N3 C1 N2 C2 175.1(4) . . . . ?
N1 C1 N2 C4 170.1(4) . . . . ?
N3 C1 N2 C4 -6.6(6) . . . . ?
N2 C1 N3 C3 157.2(4) . . . . ?
N1 C1 N3 C3 -19.3(8) . . . . ?
N2 C1 N3 C5 -2.2(5) . . . . ?
N1 C1 N3 C5 -178.7(4) . . . . ?
C1 N2 C4 C5 12.0(6) . . . . ?
C2 N2 C4 C5 -169.7(4) . . . . ?
C1 N3 C5 C4 9.3(5) . . . . ?
C3 N3 C5 C4 -150.9(4) . . . . ?
N2 C4 C5 N3 -12.2(5) . . . . ?
C14 N4 C6 C7 1.9(7) . . . . ?
Cu1 N4 C6 C7 -168.6(3) . . . . ?
N4 C6 C7 C8 4.2(7) . . . . ?
C15 N5 C8 C7 13.4(7) . . . . ?
C16 N5 C8 C7 -135.7(5) . . . . ?
C15 N5 C8 C9 -165.4(4) . . . . ?
C16 N5 C8 C9 45.5(7) . . . . ?
C6 C7 C8 N5 171.8(4) . . . . ?
C6 C7 C8 C9 -9.3(6) . . . . ?
N5 C8 C9 C10 13.3(7) . . . . ?
C7 C8 C9 C10 -165.6(4) . . . . ?
N5 C8 C9 C14 -172.6(4) . . . . ?
C7 C8 C9 C14 8.6(6) . . . . ?
C14 C9 C10 C11 4.2(7) . . . . ?
C8 C9 C10 C11 178.3(4) . . . . ?
C9 C10 C11 C12 -0.2(7) . . . . ?
C10 C11 C12 C13 -1.7(8) . . . . ?
C11 C12 C13 N1 -173.8(4) . . . . ?
C11 C12 C13 C14 -0.5(7) . . . . ?
C1 N1 C13 C12 -12.9(7) . . . . ?
Cu1 N1 C13 C12 -175.6(4) . . . . ?
C1 N1 C13 C14 173.5(4) . . . . ?
Cu1 N1 C13 C14 10.8(5) . . . . ?
C6 N4 C14 C9 -2.5(6) . . . . ?
Cu1 N4 C14 C9 169.2(3) . . . . ?
C6 N4 C14 C13 175.7(4) . . . . ?
Cu1 N4 C14 C13 -12.6(5) . . . . ?
C10 C9 C14 N4 171.7(4) . . . . ?
C8 C9 C14 N4 -2.8(7) . . . . ?
C10 C9 C14 C13 -6.4(6) . . . . ?
C8 C9 C14 C13 179.1(4) . . . . ?
C12 C13 C14 N4 -173.6(4) . . . . ?
N1 C13 C14 N4 0.6(6) . . . . ?
C12 C13 C14 C9 4.6(7) . . . . ?
N1 C13 C14 C9 178.8(4) . . . . ?
C19 N8 C17 N6 -5.6(7) . . . . ?
C21 N8 C17 N6 179.1(4) . . . . ?
C19 N8 C17 N7 170.4(4) . . . . ?
C21 N8 C17 N7 -4.8(5) . . . . ?
C29 N6 C17 N8 -49.7(6) . . . . ?
Cu1 N6 C17 N8 106.5(5) . . . . ?
C29 N6 C17 N7 134.7(4) . . . . ?
Cu1 N6 C17 N7 -69.1(5) . . . . ?
C18 N7 C17 N8 -177.2(4) . . . . ?
C20 N7 C17 N8 -9.3(5) . . . . ?
C18 N7 C17 N6 -0.9(7) . . . . ?
C20 N7 C17 N6 167.1(4) . . . . ?
C17 N7 C20 C21 18.6(5) . . . . ?
C18 N7 C20 C21 -173.1(4) . . . . ?
C17 N8 C21 C20 16.0(5) . . . . ?
C19 N8 C21 C20 -159.6(4) . . . . ?
N7 C20 C21 N8 -19.7(4) . . . . ?
C30 N9 C22 C32 -4.0(7) . . . . ?
Cu1 N9 C22 C32 -173.2(4) . . . . ?
C31 N10 C24 C32 -9.9(7) . . . . ?
C33 N10 C24 C32 135.2(5) . . . . ?
C31 N10 C24 C25 166.7(5) . . . . ?
C33 N10 C24 C25 -48.2(6) . . . . ?
N10 C24 C25 C30 178.4(4) . . . . ?
C32 C24 C25 C30 -4.9(6) . . . . ?
N10 C24 C25 C26 -5.8(7) . . . . ?
C32 C24 C25 C26 171.0(5) . . . . ?
C30 C25 C26 C27 -5.2(7) . . . . ?
C24 C25 C26 C27 178.9(4) . . . . ?
C25 C26 C27 C28 0.7(8) . . . . ?
C26 C27 C28 C29 3.9(7) . . . . ?
C27 C28 C29 N6 -178.4(4) . . . . ?
C27 C28 C29 C30 -3.8(7) . . . . ?
C17 N6 C29 C28 -11.4(7) . . . . ?
Cu1 N6 C29 C28 -170.4(4) . . . . ?
C17 N6 C29 C30 173.9(4) . . . . ?
Cu1 N6 C29 C30 14.8(5) . . . . ?
C22 N9 C30 C25 2.5(7) . . . . ?
Cu1 N9 C30 C25 173.0(3) . . . . ?
C22 N9 C30 C29 -177.0(4) . . . . ?
Cu1 N9 C30 C29 -6.6(5) . . . . ?
C26 C25 C30 N9 -174.3(4) . . . . ?
C24 C25 C30 N9 1.9(7) . . . . ?
C26 C25 C30 C29 5.2(7) . . . . ?
C24 C25 C30 C29 -178.6(4) . . . . ?
C28 C29 C30 N9 178.8(4) . . . . ?
N6 C29 C30 N9 -6.0(6) . . . . ?
C28 C29 C30 C25 -0.7(7) . . . . ?
N6 C29 C30 C25 174.4(4) . . . . ?
N9 C22 C32 C24 0.8(7) . . . . ?
N10 C24 C32 C22 -179.5(4) . . . . ?
C25 C24 C32 C22 3.8(7) . . . . ?

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 Br2 0.99 2.90 3.736(6) 142.5 1_655 yes
C7 H7 Br1 0.95 2.88 3.641(5) 137.7 2_576 yes
C12 H12 N3 0.95 2.60 3.109(6) 114.0 . yes
C16 H16A Br2 0.98 2.68 3.577(5) 151.9 2_567 yes
C21 H21B Br1 0.99 2.92 3.786(5) 146.6 2_576 yes
C28 H28 Br2 0.95 2.91 3.811(5) 159.7 2_566 yes
C32 H32 Br1 0.95 2.89 3.637(5) 136.8 2_676 yes

_refine_diff_density_max         1.301
_refine_diff_density_min         -1.183
_refine_diff_density_rms         0.142



####################################################################### 
# 
# 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_L2
_database_code_depnum_ccdc_archive 'CCDC 2118648'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H21 N5'
_chemical_formula_sum            'C13 H21 N5'
_chemical_formula_weight         247.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   7.2681(15)
_cell_length_b                   12.646(3)
_cell_length_c                   14.978(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.60(3)
_cell_angle_gamma                90
_cell_volume                     1338.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    16767
_cell_measurement_theta_min      4.63
_cell_measurement_theta_max      68.82

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.612
_shelx_estimated_absorpt_T_min   0.877
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5389
_exptl_absorpt_correction_T_max  0.9243
_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      '4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'

_diffrn_detector                 'Hybrid Pixel Counting Detector'
_diffrn_detector_type            'Dectris Pilatus 200K'
_diffrn_detector_area_resol_mean 5.81

_diffrn_source                   'sealed x-ray tube'
_diffrn_source_type              'Xenocs Cu microfocus tube'
_diffrn_radiation_probe          x-ray
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.5 mm diameter'

_diffrn_ambient_temperature      100

_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 3552 frames, detector distance = 60 mm
;
_diffrn_reflns_number            6480
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.632
_diffrn_reflns_theta_max         67.831
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             2369
_reflns_number_gt                1902
_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    'SHELXL-97 (Sheldrick, 1997)'
_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 1.77, 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)+(0.0974P)²+0.0813P] 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         2369
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1313
_refine_ls_wR_factor_gt          0.1288
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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 0.37711(17) 0.31734(10) 0.10845(8) 0.0264(3) Uani 1 1 d . . . . .
C2 C 0.31217(18) 0.40916(10) 0.06277(9) 0.0259(3) Uani 1 1 d . . . . .
H2 H 0.227303 0.405956 0.003966 0.031 Uiso 1 1 calc R U . . .
C3 C 0.37100(18) 0.50828(10) 0.10284(9) 0.0265(3) Uani 1 1 d . . . . .
C4 C 0.50379(19) 0.50453(10) 0.18859(9) 0.0293(3) Uani 1 1 d . . . . .
H4 H 0.552522 0.568028 0.219049 0.035 Uiso 1 1 calc R U . . .
C5 C 0.56163(19) 0.40781(10) 0.22741(9) 0.0295(3) Uani 1 1 d . . . . .
H5 H 0.650996 0.407872 0.285001 0.035 Uiso 1 1 calc R U . . .
C6 C 0.19160(19) 0.60418(10) -0.03227(9) 0.0306(3) Uani 1 1 d . . . . .
H6A H 0.277560 0.596521 -0.073404 0.046 Uiso 1 1 calc R U . . .
H6B H 0.124530 0.671819 -0.044332 0.046 Uiso 1 1 calc R U . . .
H6C H 0.099716 0.546126 -0.043000 0.046 Uiso 1 1 calc R U . . .
C7 C 0.3858(2) 0.70138(11) 0.09883(10) 0.0375(4) Uani 1 1 d . . . . .
H7A H 0.507037 0.710097 0.081756 0.056 Uiso 1 1 calc R U . . .
H7B H 0.406879 0.701727 0.165904 0.056 Uiso 1 1 calc R U . . .
H7C H 0.300964 0.759656 0.073026 0.056 Uiso 1 1 calc R U . . .
N8 N 0.50215(15) 0.31333(9) 0.19060(7) 0.0290(3) Uani 1 1 d . . . . .
N9 N 0.30023(16) 0.60134(8) 0.06289(8) 0.0302(3) Uani 1 1 d . . . . .
N10 N 0.17225(15) 0.21698(8) -0.01746(7) 0.0282(3) Uani 1 1 d . . . . .
N11 N 0.23252(15) 0.04116(8) -0.07069(7) 0.0289(3) Uani 1 1 d . . . . .
N12 N 0.03496(15) 0.15369(8) -0.16390(7) 0.0282(3) Uani 1 1 d . . . . .
C13 C 0.31067(19) 0.20942(10) 0.06965(9) 0.0295(3) Uani 1 1 d . . . . .
H13A H 0.421011 0.168231 0.061003 0.035 Uiso 1 1 calc R U . . .
H13B H 0.254124 0.170972 0.114223 0.035 Uiso 1 1 calc R U . . .
C14 C 0.15130(17) 0.14180(10) -0.07622(9) 0.0255(3) Uani 1 1 d . . . . .
C15 C 0.0013(2) 0.25996(11) -0.20191(10) 0.0347(3) Uani 1 1 d . . . . .
H15A H 0.114235 0.284853 -0.220688 0.052 Uiso 1 1 calc R U . . .
H15B H -0.026420 0.307715 -0.155233 0.052 Uiso 1 1 calc R U . . .
H15C H -0.106514 0.258757 -0.255364 0.052 Uiso 1 1 calc R U . . .
C16 C 0.2576(2) -0.02360(10) 0.01196(10) 0.0328(3) Uani 1 1 d . . . . .
H16A H 0.152432 -0.073827 0.004886 0.049 Uiso 1 1 calc R U . . .
H16B H 0.259849 0.022028 0.065092 0.049 Uiso 1 1 calc R U . . .
H16C H 0.377222 -0.062491 0.021391 0.049 Uiso 1 1 calc R U . . .
C17 C 0.1562(2) -0.01539(11) -0.15634(9) 0.0332(3) Uani 1 1 d . . . . .
H17A H 0.052091 -0.063359 -0.150339 0.040 Uiso 1 1 calc R U . . .
H17B H 0.255818 -0.056961 -0.175428 0.040 Uiso 1 1 calc R U . . .
C18 C 0.08420(19) 0.07300(11) -0.22368(9) 0.0333(3) Uani 1 1 d . . . . .
H18A H 0.183769 0.098193 -0.253689 0.040 Uiso 1 1 calc R U . . .
H18B H -0.027819 0.050520 -0.271344 0.040 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 N8 1.3479(18) . ?
C1 C2 1.3738(18) . ?
C1 C13 1.5170(18) . ?
C2 C3 1.4119(18) . ?
C2 H2 0.9500 . ?
C3 N9 1.3649(17) . ?
C3 C4 1.4143(19) . ?
C4 C5 1.3769(19) . ?
C4 H4 0.9500 . ?
C5 N8 1.3440(17) . ?
C5 H5 0.9500 . ?
C6 N9 1.4584(18) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 N9 1.4558(17) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
N10 C14 1.2800(17) . ?
N10 C13 1.4514(17) . ?
N11 C14 1.3972(17) . ?
N11 C16 1.4596(18) . ?
N11 C17 1.4596(18) . ?
N12 C14 1.3930(17) . ?
N12 C18 1.4565(18) . ?
N12 C15 1.4575(18) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.514(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 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
N8 C1 C2 124.43(11) . . ?
N8 C1 C13 113.67(11) . . ?
C2 C1 C13 121.90(11) . . ?
C1 C2 C3 120.29(12) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
N9 C3 C2 122.26(12) . . ?
N9 C3 C4 122.24(11) . . ?
C2 C3 C4 115.47(11) . . ?
C5 C4 C3 119.26(11) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N8 C5 C4 125.42(12) . . ?
N8 C5 H5 117.3 . . ?
C4 C5 H5 117.3 . . ?
N9 C6 H6A 109.5 . . ?
N9 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N9 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N9 C7 H7A 109.5 . . ?
N9 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N9 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 N8 C1 115.08(11) . . ?
C3 N9 C7 120.20(11) . . ?
C3 N9 C6 120.76(10) . . ?
C7 N9 C6 115.21(11) . . ?
C14 N10 C13 120.96(10) . . ?
C14 N11 C16 121.87(11) . . ?
C14 N11 C17 109.04(10) . . ?
C16 N11 C17 114.61(10) . . ?
C14 N12 C18 108.76(10) . . ?
C14 N12 C15 118.47(10) . . ?
C18 N12 C15 116.66(11) . . ?
N10 C13 C1 112.09(10) . . ?
N10 C13 H13A 109.2 . . ?
C1 C13 H13A 109.2 . . ?
N10 C13 H13B 109.2 . . ?
C1 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
N10 C14 N12 121.05(11) . . ?
N10 C14 N11 130.96(12) . . ?
N12 C14 N11 107.97(11) . . ?
N12 C15 H15A 109.5 . . ?
N12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N11 C16 H16A 109.5 . . ?
N11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N11 C17 C18 102.96(10) . . ?
N11 C17 H17A 111.2 . . ?
C18 C17 H17A 111.2 . . ?
N11 C17 H17B 111.2 . . ?
C18 C17 H17B 111.2 . . ?
H17A C17 H17B 109.1 . . ?
N12 C18 C17 101.77(11) . . ?
N12 C18 H18A 111.4 . . ?
C17 C18 H18A 111.4 . . ?
N12 C18 H18B 111.4 . . ?
C17 C18 H18B 111.4 . . ?
H18A C18 H18B 109.3 . . ?

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
N8 C1 C2 C3 -2.2(2) . . . . ?
C13 C1 C2 C3 177.27(11) . . . . ?
C1 C2 C3 N9 -175.41(11) . . . . ?
C1 C2 C3 C4 2.69(19) . . . . ?
N9 C3 C4 C5 176.47(12) . . . . ?
C2 C3 C4 C5 -1.63(19) . . . . ?
C3 C4 C5 N8 -0.1(2) . . . . ?
C4 C5 N8 C1 0.71(19) . . . . ?
C2 C1 N8 C5 0.44(19) . . . . ?
C13 C1 N8 C5 -179.08(11) . . . . ?
C2 C3 N9 C7 -170.33(12) . . . . ?
C4 C3 N9 C7 11.7(2) . . . . ?
C2 C3 N9 C6 -13.43(19) . . . . ?
C4 C3 N9 C6 168.60(11) . . . . ?
C14 N10 C13 C1 153.93(12) . . . . ?
N8 C1 C13 N10 178.34(10) . . . . ?
C2 C1 C13 N10 -1.20(18) . . . . ?
C13 N10 C14 N12 -172.41(11) . . . . ?
C13 N10 C14 N11 5.7(2) . . . . ?
C18 N12 C14 N10 161.74(12) . . . . ?
C15 N12 C14 N10 25.42(17) . . . . ?
C18 N12 C14 N11 -16.78(13) . . . . ?
C15 N12 C14 N11 -153.10(11) . . . . ?
C16 N11 C14 N10 41.07(19) . . . . ?
C17 N11 C14 N10 178.23(13) . . . . ?
C16 N11 C14 N12 -140.62(11) . . . . ?
C17 N11 C14 N12 -3.45(14) . . . . ?
C14 N11 C17 C18 21.00(14) . . . . ?
C16 N11 C17 C18 161.57(11) . . . . ?
C14 N12 C18 C17 28.91(13) . . . . ?
C15 N12 C18 C17 166.12(11) . . . . ?
N11 C17 C18 N12 -29.34(13) . . . . ?

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
C7 H7B N8 0.98 2.53 3.3775(19) 145.2 2_655 yes

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.049
















####################################################################### 
# 
# 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-I
_database_code_depnum_ccdc_archive 'CCDC 2118644'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-07-28 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         'C16 H21 Br Cu N5'
_chemical_formula_sum            'C16 H21 Br Cu N5'
_chemical_formula_weight         426.83

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/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                   14.212(3)
_cell_length_b                   8.3493(17)
_cell_length_c                   14.873(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.54(3)
_cell_angle_gamma                90
_cell_volume                     1691.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    23807
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      33.61

_exptl_crystal_description       block
_exptl_crystal_colour            yellow

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    3.659
_shelx_estimated_absorpt_T_min   0.628
_shelx_estimated_absorpt_T_max   0.810
_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  0.2864
_exptl_absorpt_correction_T_max  0.8633

_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      
; 1231 frames, detector distance = 60 mm
;

_diffrn_reflns_number            39814
_diffrn_reflns_av_unetI/netI     0.0731
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.823
_diffrn_reflns_theta_max         34.021
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6522
_reflns_number_gt                4206
_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)+(0.0599P)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         6522
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1194
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.23850(2) 0.23623(4) 0.50332(3) 0.01704(9) Uani 1 1 d . . . . .
N1 N 0.23755(15) 0.3761(3) 0.61431(16) 0.0134(4) Uani 1 1 d . . . . .
C1 C 0.16240(18) 0.4624(3) 0.62216(19) 0.0142(5) Uani 1 1 d . . . . .
N2 N 0.16047(16) 0.6208(3) 0.63988(17) 0.0162(5) Uani 1 1 d . . . . .
C2 C 0.2289(2) 0.7381(4) 0.6228(2) 0.0193(6) Uani 1 1 d . . . . .
H2A H 0.273946 0.685610 0.593001 0.029 Uiso 1 1 calc R U . . .
H2B H 0.266485 0.785511 0.682545 0.029 Uiso 1 1 calc R U . . .
H2C H 0.192462 0.822371 0.581458 0.029 Uiso 1 1 calc R U . . .
N3 N 0.07083(16) 0.3990(3) 0.60737(17) 0.0191(5) Uani 1 1 d . . . . .
C3 C 0.0619(2) 0.6735(4) 0.6370(2) 0.0246(7) Uani 1 1 d . . . . .
H3A H 0.032454 0.738768 0.580383 0.030 Uiso 1 1 calc R U . . .
H3B H 0.062330 0.736455 0.693473 0.030 Uiso 1 1 calc R U . . .
N4 N 0.38184(15) 0.3069(3) 0.53812(16) 0.0122(4) Uani 1 1 d . . . . .
C4 C 0.0553(2) 0.2305(4) 0.6223(2) 0.0254(7) Uani 1 1 d . . . . .
H4A H -0.013659 0.203225 0.592959 0.038 Uiso 1 1 calc R U . . .
H4B H 0.072030 0.208825 0.689808 0.038 Uiso 1 1 calc R U . . .
H4C H 0.097185 0.165714 0.594374 0.038 Uiso 1 1 calc R U . . .
N5 N 0.67890(15) 0.4285(3) 0.66139(16) 0.0143(5) Uani 1 1 d . . . . .
C5 C 0.0070(2) 0.5157(4) 0.6340(2) 0.0248(7) Uani 1 1 d . . . . .
H5A H -0.001619 0.489901 0.696181 0.030 Uiso 1 1 calc R U . . .
H5B H -0.058230 0.519707 0.587051 0.030 Uiso 1 1 calc R U . . .
C6 C 0.45175(19) 0.2694(3) 0.49896(19) 0.0134(5) Uani 1 1 d . . . . .
H6 H 0.433365 0.212639 0.441225 0.016 Uiso 1 1 calc R U . . .
C7 C 0.55086(19) 0.3080(3) 0.53707(19) 0.0139(5) Uani 1 1 d . . . . .
H7 H 0.597003 0.279438 0.504506 0.017 Uiso 1 1 calc R U . . .
C8 C 0.58194(17) 0.3873(3) 0.62159(19) 0.0117(5) Uani 1 1 d . . . . .
C9 C 0.50952(17) 0.4180(3) 0.67163(18) 0.0111(5) Uani 1 1 d . . . . .
C10 C 0.53146(19) 0.4725(3) 0.76498(19) 0.0132(5) Uani 1 1 d . . . . .
H10 H 0.597819 0.490127 0.799993 0.016 Uiso 1 1 calc R U . . .
C11 C 0.45807(19) 0.5001(3) 0.80540(19) 0.0134(5) Uani 1 1 d . . . . .
H11 H 0.474361 0.535211 0.868724 0.016 Uiso 1 1 calc R U . . .
C12 C 0.35904(19) 0.4777(3) 0.7557(2) 0.0145(5) Uani 1 1 d . . . . .
H12 H 0.309150 0.503664 0.784296 0.017 Uiso 1 1 calc R U . . .
C13 C 0.33391(18) 0.4184(3) 0.66555(19) 0.0123(5) Uani 1 1 d . . . . .
C14 C 0.40978(18) 0.3822(3) 0.62319(19) 0.0109(5) Uani 1 1 d . . . . .
C15 C 0.7070(2) 0.5835(4) 0.7072(2) 0.0190(6) Uani 1 1 d . . . . .
H15A H 0.744204 0.644750 0.672609 0.028 Uiso 1 1 calc R U . . .
H15B H 0.747793 0.566338 0.771714 0.028 Uiso 1 1 calc R U . . .
H15C H 0.647857 0.643179 0.707947 0.028 Uiso 1 1 calc R U . . .
C16 C 0.75275(19) 0.3624(4) 0.6213(2) 0.0201(6) Uani 1 1 d . . . . .
H16A H 0.739064 0.248625 0.607125 0.030 Uiso 1 1 calc R U . . .
H16B H 0.817859 0.373963 0.666222 0.030 Uiso 1 1 calc R U . . .
H16C H 0.751042 0.419940 0.563391 0.030 Uiso 1 1 calc R U . . .
Br1 Br 0.14983(2) 0.06883(4) 0.39203(2) 0.02263(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 2.025(2) . ?
Cu1 N4 2.041(2) . ?
Cu1 Br1 2.2569(7) . ?
N1 C1 1.321(3) . ?
N1 C13 1.409(3) . ?
C1 N2 1.350(4) . ?
C1 N3 1.363(3) . ?
N2 C2 1.453(4) . ?
N2 C3 1.457(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N3 C4 1.451(4) . ?
N3 C5 1.461(4) . ?
C3 C5 1.525(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
N4 C6 1.324(3) . ?
N4 C14 1.367(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N5 C8 1.380(3) . ?
N5 C16 1.456(4) . ?
N5 C15 1.464(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.398(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.377(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.454(4) . ?
C9 C10 1.409(4) . ?
C9 C14 1.427(3) . ?
C10 C11 1.364(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.403(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.427(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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 N4 82.21(9) . . ?
N1 Cu1 Br1 145.39(6) . . ?
N4 Cu1 Br1 132.34(7) . . ?
C1 N1 C13 120.1(2) . . ?
C1 N1 Cu1 125.44(18) . . ?
C13 N1 Cu1 110.75(17) . . ?
N1 C1 N2 127.8(2) . . ?
N1 C1 N3 122.2(3) . . ?
N2 C1 N3 109.9(2) . . ?
C1 N2 C2 125.1(2) . . ?
C1 N2 C3 111.3(2) . . ?
C2 N2 C3 118.5(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 122.1(2) . . ?
C1 N3 C5 109.6(3) . . ?
C4 N3 C5 118.2(3) . . ?
N2 C3 C5 102.7(2) . . ?
N2 C3 H3A 111.2 . . ?
C5 C3 H3A 111.2 . . ?
N2 C3 H3B 111.2 . . ?
C5 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
C6 N4 C14 117.3(2) . . ?
C6 N4 Cu1 129.78(19) . . ?
C14 N4 Cu1 111.94(17) . . ?
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 . . ?
C8 N5 C16 118.5(2) . . ?
C8 N5 C15 121.8(2) . . ?
C16 N5 C15 113.2(2) . . ?
N3 C5 C3 103.4(2) . . ?
N3 C5 H5A 111.1 . . ?
C3 C5 H5A 111.1 . . ?
N3 C5 H5B 111.1 . . ?
C3 C5 H5B 111.1 . . ?
H5A C5 H5B 109.0 . . ?
N4 C6 C7 124.2(3) . . ?
N4 C6 H6 117.9 . . ?
C7 C6 H6 117.9 . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 N5 122.2(2) . . ?
C7 C8 C9 117.5(2) . . ?
N5 C8 C9 120.2(2) . . ?
C10 C9 C14 118.3(2) . . ?
C10 C9 C8 124.8(2) . . ?
C14 C9 C8 116.8(2) . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 121.6(3) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 N1 124.0(2) . . ?
C12 C13 C14 119.1(2) . . ?
N1 C13 C14 116.6(2) . . ?
N4 C14 C9 123.3(2) . . ?
N4 C14 C13 116.7(2) . . ?
C9 C14 C13 120.0(2) . . ?
N5 C15 H15A 109.5 . . ?
N5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N5 C16 H16A 109.5 . . ?
N5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C13 N1 C1 N2 30.7(4) . . . . ?
Cu1 N1 C1 N2 -125.5(3) . . . . ?
C13 N1 C1 N3 -153.1(3) . . . . ?
Cu1 N1 C1 N3 50.7(4) . . . . ?
N1 C1 N2 C2 22.2(4) . . . . ?
N3 C1 N2 C2 -154.4(3) . . . . ?
N1 C1 N2 C3 176.2(3) . . . . ?
N3 C1 N2 C3 -0.4(3) . . . . ?
N1 C1 N3 C4 27.4(4) . . . . ?
N2 C1 N3 C4 -155.8(3) . . . . ?
N1 C1 N3 C5 171.9(3) . . . . ?
N2 C1 N3 C5 -11.3(3) . . . . ?
C1 N2 C3 C5 11.0(3) . . . . ?
C2 N2 C3 C5 166.9(2) . . . . ?
C1 N3 C5 C3 17.4(3) . . . . ?
C4 N3 C5 C3 163.5(2) . . . . ?
N2 C3 C5 N3 -16.5(3) . . . . ?
C14 N4 C6 C7 -2.9(4) . . . . ?
Cu1 N4 C6 C7 -170.8(2) . . . . ?
N4 C6 C7 C8 1.4(4) . . . . ?
C6 C7 C8 N5 -179.6(2) . . . . ?
C6 C7 C8 C9 4.3(4) . . . . ?
C16 N5 C8 C7 -10.8(4) . . . . ?
C15 N5 C8 C7 139.0(3) . . . . ?
C16 N5 C8 C9 165.2(2) . . . . ?
C15 N5 C8 C9 -45.0(4) . . . . ?
C7 C8 C9 C10 168.8(3) . . . . ?
N5 C8 C9 C10 -7.5(4) . . . . ?
C7 C8 C9 C14 -8.0(4) . . . . ?
N5 C8 C9 C14 175.8(2) . . . . ?
C14 C9 C10 C11 -4.3(4) . . . . ?
C8 C9 C10 C11 179.0(3) . . . . ?
C9 C10 C11 C12 -1.0(4) . . . . ?
C10 C11 C12 C13 3.6(4) . . . . ?
C11 C12 C13 N1 172.9(3) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C1 N1 C13 C12 37.3(4) . . . . ?
Cu1 N1 C13 C12 -163.3(2) . . . . ?
C1 N1 C13 C14 -148.8(3) . . . . ?
Cu1 N1 C13 C14 10.6(3) . . . . ?
C6 N4 C14 C9 -1.5(4) . . . . ?
Cu1 N4 C14 C9 168.5(2) . . . . ?
C6 N4 C14 C13 -178.6(2) . . . . ?
Cu1 N4 C14 C13 -8.6(3) . . . . ?
C10 C9 C14 N4 -170.1(3) . . . . ?
C8 C9 C14 N4 6.9(4) . . . . ?
C10 C9 C14 C13 6.9(4) . . . . ?
C8 C9 C14 C13 -176.1(2) . . . . ?
C12 C13 C14 N4 172.8(2) . . . . ?
N1 C13 C14 N4 -1.4(4) . . . . ?
C12 C13 C14 C9 -4.4(4) . . . . ?
N1 C13 C14 C9 -178.6(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
C2 H2B N5 0.98 2.53 3.486(4) 165.6 2_656 yes

_refine_diff_density_max         0.906
_refine_diff_density_min         -1.253
_refine_diff_density_rms         0.136


####################################################################### 
# 
# 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_C6I
_database_code_depnum_ccdc_archive 'CCDC 2118646'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H16 Br Cu N4'
_chemical_formula_sum            'C11 H16 Br Cu N4'
_chemical_formula_weight         347.73

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/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                   13.9718(8)
_cell_length_b                   8.0130(6)
_cell_length_c                   23.5855(15)
_cell_angle_alpha                90
_cell_angle_beta                 99.071(6)
_cell_angle_gamma                90
_cell_volume                     2607.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4195
_cell_measurement_theta_min      2.1032
_cell_measurement_theta_max      29.1130

_exptl_crystal_description       column
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    4.723
_shelx_estimated_absorpt_T_min   0.397
_shelx_estimated_absorpt_T_max   0.765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.63481
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) 
(compiled Oct 24 2008,09:44:38) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.0560

_diffrn_reflns_number            20124
_diffrn_reflns_av_unetI/netI     0.1444
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.103
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4842
_reflns_number_gt                2338
_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       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;


_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)+(0.0188P)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         4842
_refine_ls_number_parameters     311
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0554
_refine_ls_wR_factor_gt          0.0516
_refine_ls_goodness_of_fit_ref   0.710
_refine_ls_restrained_S_all      0.710
_refine_ls_shift/su_max          0.019
_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 0.65468(4) 1.03662(8) 0.38761(2) 0.02688(17) Uani 1 1 d . . . . .
Cu2 Cu 0.87111(4) 0.51990(8) 0.62879(2) 0.02424(17) Uani 1 1 d . . . . .
Br1 Br 0.50319(3) 1.14367(8) 0.36589(2) 0.04313(19) Uani 1 1 d . . . . .
Br2 Br 1.01928(3) 0.64166(7) 0.64216(2) 0.03202(16) Uani 1 1 d . . . . .
N1 N 0.7717(2) 0.9104(4) 0.37445(14) 0.0197(10) Uani 1 1 d . . . . .
N2 N 0.7230(3) 0.8010(5) 0.28282(15) 0.0298(11) Uani 1 1 d . . . . .
N3 N 0.8800(3) 0.7842(5) 0.31700(15) 0.0233(10) Uani 1 1 d . . . . .
N4 N 0.7217(2) 1.0332(5) 0.47352(13) 0.0187(9) Uani 1 1 d . . . . .
N5 N 0.7470(2) 0.5006(5) 0.57297(13) 0.0199(9) Uani 1 1 d . . . . .
N6 N 0.6421(2) 0.5460(5) 0.48343(13) 0.0210(9) Uani 1 1 d . . . . .
N7 N 0.7993(3) 0.4831(5) 0.48335(13) 0.0212(9) Uani 1 1 d . . . . .
N8 N 0.7897(2) 0.4071(4) 0.68344(13) 0.0190(9) Uani 1 1 d . . . . .
C1 C 0.7917(3) 0.8392(6) 0.32883(19) 0.0199(11) Uani 1 1 d . . . . .
C2 C 0.6196(3) 0.7858(7) 0.28413(17) 0.0361(14) Uani 1 1 d . . . . .
H2A H 0.598095 0.879769 0.305559 0.054 Uiso 1 1 calc R U . . .
H2B H 0.606869 0.680885 0.302918 0.054 Uiso 1 1 calc R U . . .
H2C H 0.584267 0.786650 0.244790 0.054 Uiso 1 1 calc R U . . .
C3 C 0.7629(3) 0.6950(7) 0.24331(18) 0.0352(15) Uani 1 1 d . . . . .
H3A H 0.743741 0.734419 0.203349 0.042 Uiso 1 1 calc R U . . .
H3B H 0.740498 0.578580 0.246111 0.042 Uiso 1 1 calc R U . . .
C4 C 0.8700(3) 0.7066(7) 0.26088(18) 0.0349(14) Uani 1 1 d . . . . .
H4A H 0.900313 0.594550 0.263185 0.042 Uiso 1 1 calc R U . . .
H4B H 0.899812 0.776173 0.233676 0.042 Uiso 1 1 calc R U . . .
C5 C 0.9732(3) 0.8644(7) 0.33784(19) 0.0384(14) Uani 1 1 d . . . . .
H5A H 0.962294 0.981352 0.347181 0.058 Uiso 1 1 calc R U . . .
H5B H 1.014554 0.859078 0.307975 0.058 Uiso 1 1 calc R U . . .
H5C H 1.005033 0.806410 0.372299 0.058 Uiso 1 1 calc R U . . .
C6 C 0.8462(3) 0.9108(6) 0.42553(16) 0.0252(12) Uani 1 1 d . . . . .
H6A H 0.895335 0.996605 0.420935 0.030 Uiso 1 1 calc R U . . .
H6B H 0.879045 0.800928 0.429014 0.030 Uiso 1 1 calc R U . . .
C7 C 0.8049(3) 0.9459(6) 0.48031(18) 0.0206(12) Uani 1 1 d . . . . .
C8 C 0.8515(3) 0.8981(6) 0.53369(18) 0.0262(13) Uani 1 1 d . . . . .
H8A H 0.909957 0.835731 0.537194 0.031 Uiso 1 1 calc R U . . .
C9 C 0.8136(4) 0.9405(6) 0.58138(19) 0.0307(14) Uani 1 1 d . . . . .
H9A H 0.844977 0.906824 0.618277 0.037 Uiso 1 1 calc R U . . .
C10 C 0.7294(4) 1.0324(6) 0.57589(19) 0.0308(13) Uani 1 1 d . . . . .
H10A H 0.702473 1.065762 0.608679 0.037 Uiso 1 1 calc R U . . .
C11 C 0.6848(3) 1.0752(6) 0.52054(19) 0.0284(13) Uani 1 1 d . . . . .
H11A H 0.625980 1.136630 0.516134 0.034 Uiso 1 1 calc R U . . .
C12 C 0.7297(3) 0.5122(6) 0.51723(18) 0.0187(12) Uani 1 1 d . . . . .
C13 C 0.5793(3) 0.6751(6) 0.49904(17) 0.0272(12) Uani 1 1 d . . . . .
H13A H 0.525405 0.624216 0.514846 0.041 Uiso 1 1 calc R U . . .
H13B H 0.553736 0.740753 0.464940 0.041 Uiso 1 1 calc R U . . .
H13C H 0.616020 0.748142 0.527942 0.041 Uiso 1 1 calc R U . . .
C14 C 0.6562(3) 0.5474(6) 0.42278(16) 0.0306(13) Uani 1 1 d . . . . .
H14A H 0.660298 0.663047 0.408550 0.037 Uiso 1 1 calc R U . . .
H14B H 0.602736 0.488509 0.398205 0.037 Uiso 1 1 calc R U . . .
C15 C 0.7510(3) 0.4566(6) 0.42397(16) 0.0273(13) Uani 1 1 d . . . . .
H15A H 0.740423 0.336356 0.415578 0.033 Uiso 1 1 calc R U . . .
H15B H 0.789225 0.505044 0.396037 0.033 Uiso 1 1 calc R U . . .
C16 C 0.8851(3) 0.3830(6) 0.50419(17) 0.0270(13) Uani 1 1 d . . . . .
H16A H 0.926741 0.444071 0.534576 0.040 Uiso 1 1 calc R U . . .
H16B H 0.920869 0.360738 0.472459 0.040 Uiso 1 1 calc R U . . .
H16C H 0.865084 0.277135 0.519520 0.040 Uiso 1 1 calc R U . . .
C17 C 0.6658(3) 0.4926(6) 0.60438(15) 0.0210(12) Uani 1 1 d . . . . .
H17A H 0.611665 0.431281 0.581319 0.025 Uiso 1 1 calc R U . . .
H17B H 0.643150 0.607119 0.610831 0.025 Uiso 1 1 calc R U . . .
C18 C 0.6941(3) 0.4063(6) 0.66147(16) 0.0163(11) Uani 1 1 d . U . . .
C19 C 0.6261(3) 0.3366(6) 0.68955(18) 0.0288(13) Uani 1 1 d . . . . .
H19A H 0.559886 0.335888 0.672362 0.035 Uiso 1 1 calc R U . . .
C20 C 0.6540(3) 0.2664(7) 0.74342(19) 0.0316(14) Uani 1 1 d . . . . .
H20A H 0.607299 0.219778 0.764026 0.038 Uiso 1 1 calc R U . . .
C21 C 0.7505(3) 0.2660(6) 0.76623(18) 0.0256(13) Uani 1 1 d . . . . .
H21A H 0.772215 0.216689 0.802621 0.031 Uiso 1 1 calc R U . . .
C22 C 0.8154(3) 0.3383(6) 0.73536(17) 0.0229(12) Uani 1 1 d . . . . .
H22A H 0.882024 0.339416 0.751775 0.028 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 N1 1.989(3) . ?
Cu1 N4 2.094(3) . ?
Cu1 Br1 2.2663(8) . ?
Cu2 N5 2.011(3) . ?
Cu2 N8 2.058(3) . ?
Cu2 Br2 2.2652(7) . ?
N1 C1 1.287(5) . ?
N1 C6 1.462(5) . ?
N2 C1 1.366(5) . ?
N2 C3 1.437(5) . ?
N2 C2 1.455(5) . ?
N3 C1 1.378(5) . ?
N3 C4 1.449(5) . ?
N3 C5 1.466(5) . ?
N4 C11 1.337(5) . ?
N4 C7 1.345(5) . ?
N5 C12 1.302(5) . ?
N5 C17 1.451(5) . ?
N6 C12 1.378(5) . ?
N6 C13 1.441(5) . ?
N6 C14 1.475(5) . ?
N7 C12 1.373(5) . ?
N7 C16 1.460(5) . ?
N7 C15 1.471(4) . ?
N8 C22 1.339(5) . ?
N8 C18 1.355(5) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.491(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.522(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.377(5) . ?
C8 C9 1.360(6) . ?
C8 H8A 0.9500 . ?
C9 C10 1.376(6) . ?
C9 H9A 0.9500 . ?
C10 C11 1.398(6) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.508(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.510(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.360(6) . ?
C19 C20 1.388(5) . ?
C19 H19A 0.9500 . ?
C20 C21 1.370(5) . ?
C20 H20A 0.9500 . ?
C21 C22 1.377(6) . ?
C21 H21A 0.9500 . ?
C22 H22A 0.9500 . ?

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 83.75(14) . . ?
N1 Cu1 Br1 156.78(10) . . ?
N4 Cu1 Br1 118.87(10) . . ?
N5 Cu2 N8 82.63(13) . . ?
N5 Cu2 Br2 143.04(10) . . ?
N8 Cu2 Br2 133.25(9) . . ?
C1 N1 C6 118.0(4) . . ?
C1 N1 Cu1 130.4(3) . . ?
C6 N1 Cu1 111.5(3) . . ?
C1 N2 C3 110.6(4) . . ?
C1 N2 C2 125.3(4) . . ?
C3 N2 C2 116.9(4) . . ?
C1 N3 C4 111.2(4) . . ?
C1 N3 C5 124.6(4) . . ?
C4 N3 C5 116.5(4) . . ?
C11 N4 C7 118.1(4) . . ?
C11 N4 Cu1 128.9(3) . . ?
C7 N4 Cu1 111.6(3) . . ?
C12 N5 C17 118.9(3) . . ?
C12 N5 Cu2 131.3(3) . . ?
C17 N5 Cu2 109.4(2) . . ?
C12 N6 C13 120.9(4) . . ?
C12 N6 C14 108.7(3) . . ?
C13 N6 C14 115.0(3) . . ?
C12 N7 C16 121.1(3) . . ?
C12 N7 C15 108.5(3) . . ?
C16 N7 C15 118.0(3) . . ?
C22 N8 C18 117.0(4) . . ?
C22 N8 Cu2 131.2(3) . . ?
C18 N8 Cu2 111.8(3) . . ?
N1 C1 N2 123.1(4) . . ?
N1 C1 N3 129.0(4) . . ?
N2 C1 N3 107.9(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 C4 105.0(4) . . ?
N2 C3 H3A 110.8 . . ?
C4 C3 H3A 110.8 . . ?
N2 C3 H3B 110.8 . . ?
C4 C3 H3B 110.8 . . ?
H3A C3 H3B 108.8 . . ?
N3 C4 C3 103.2(4) . . ?
N3 C4 H4A 111.1 . . ?
C3 C4 H4A 111.1 . . ?
N3 C4 H4B 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
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 . . ?
N1 C6 C7 112.6(3) . . ?
N1 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
N1 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
N4 C7 C8 121.9(4) . . ?
N4 C7 C6 115.5(4) . . ?
C8 C7 C6 122.5(4) . . ?
C9 C8 C7 119.8(4) . . ?
C9 C8 H8A 120.1 . . ?
C7 C8 H8A 120.1 . . ?
C8 C9 C10 119.6(4) . . ?
C8 C9 H9A 120.2 . . ?
C10 C9 H9A 120.2 . . ?
C9 C10 C11 117.8(4) . . ?
C9 C10 H10A 121.1 . . ?
C11 C10 H10A 121.1 . . ?
N4 C11 C10 122.7(4) . . ?
N4 C11 H11A 118.7 . . ?
C10 C11 H11A 118.7 . . ?
N5 C12 N7 122.6(4) . . ?
N5 C12 N6 127.2(4) . . ?
N7 C12 N6 110.1(3) . . ?
N6 C13 H13A 109.5 . . ?
N6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N6 C14 C15 103.3(3) . . ?
N6 C14 H14A 111.1 . . ?
C15 C14 H14A 111.1 . . ?
N6 C14 H14B 111.1 . . ?
C15 C14 H14B 111.1 . . ?
H14A C14 H14B 109.1 . . ?
N7 C15 C14 102.6(3) . . ?
N7 C15 H15A 111.2 . . ?
C14 C15 H15A 111.2 . . ?
N7 C15 H15B 111.2 . . ?
C14 C15 H15B 111.2 . . ?
H15A C15 H15B 109.2 . . ?
N7 C16 H16A 109.5 . . ?
N7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N5 C17 C18 111.1(3) . . ?
N5 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
N5 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
N8 C18 C19 122.5(4) . . ?
N8 C18 C17 116.3(4) . . ?
C19 C18 C17 121.2(4) . . ?
C18 C19 C20 119.7(4) . . ?
C18 C19 H19A 120.2 . . ?
C20 C19 H19A 120.2 . . ?
C21 C20 C19 118.5(4) . . ?
C21 C20 H20A 120.7 . . ?
C19 C20 H20A 120.7 . . ?
C20 C21 C22 118.7(4) . . ?
C20 C21 H21A 120.6 . . ?
C22 C21 H21A 120.6 . . ?
N8 C22 C21 123.6(4) . . ?
N8 C22 H22A 118.2 . . ?
C21 C22 H22A 118.2 . . ?

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
C6 N1 C1 N2 166.3(4) . . . . ?
Cu1 N1 C1 N2 -17.6(7) . . . . ?
C6 N1 C1 N3 -11.8(7) . . . . ?
Cu1 N1 C1 N3 164.4(3) . . . . ?
C3 N2 C1 N1 -169.0(4) . . . . ?
C2 N2 C1 N1 -19.8(7) . . . . ?
C3 N2 C1 N3 9.4(5) . . . . ?
C2 N2 C1 N3 158.6(4) . . . . ?
C4 N3 C1 N1 178.4(5) . . . . ?
C5 N3 C1 N1 -33.4(7) . . . . ?
C4 N3 C1 N2 0.1(5) . . . . ?
C5 N3 C1 N2 148.3(4) . . . . ?
C1 N2 C3 C4 -14.7(5) . . . . ?
C2 N2 C3 C4 -166.8(4) . . . . ?
C1 N3 C4 C3 -8.9(5) . . . . ?
C5 N3 C4 C3 -159.9(4) . . . . ?
N2 C3 C4 N3 13.7(5) . . . . ?
C1 N1 C6 C7 -161.4(4) . . . . ?
Cu1 N1 C6 C7 21.7(4) . . . . ?
C11 N4 C7 C8 0.7(6) . . . . ?
Cu1 N4 C7 C8 -166.8(3) . . . . ?
C11 N4 C7 C6 -176.5(4) . . . . ?
Cu1 N4 C7 C6 15.9(5) . . . . ?
N1 C6 C7 N4 -25.4(5) . . . . ?
N1 C6 C7 C8 157.3(4) . . . . ?
N4 C7 C8 C9 -0.5(7) . . . . ?
C6 C7 C8 C9 176.6(4) . . . . ?
C7 C8 C9 C10 -0.7(7) . . . . ?
C8 C9 C10 C11 1.5(7) . . . . ?
C7 N4 C11 C10 0.2(7) . . . . ?
Cu1 N4 C11 C10 165.2(3) . . . . ?
C9 C10 C11 N4 -1.3(7) . . . . ?
C17 N5 C12 N7 -165.0(4) . . . . ?
Cu2 N5 C12 N7 23.9(7) . . . . ?
C17 N5 C12 N6 11.7(7) . . . . ?
Cu2 N5 C12 N6 -159.4(4) . . . . ?
C16 N7 C12 N5 21.8(6) . . . . ?
C15 N7 C12 N5 163.1(4) . . . . ?
C16 N7 C12 N6 -155.4(4) . . . . ?
C15 N7 C12 N6 -14.1(5) . . . . ?
C13 N6 C12 N5 43.7(7) . . . . ?
C14 N6 C12 N5 179.9(5) . . . . ?
C13 N6 C12 N7 -139.2(4) . . . . ?
C14 N6 C12 N7 -3.0(5) . . . . ?
C12 N6 C14 C15 18.1(5) . . . . ?
C13 N6 C14 C15 157.1(4) . . . . ?
C12 N7 C15 C14 24.5(5) . . . . ?
C16 N7 C15 C14 167.2(4) . . . . ?
N6 C14 C15 N7 -25.0(4) . . . . ?
C12 N5 C17 C18 155.0(4) . . . . ?
Cu2 N5 C17 C18 -32.1(4) . . . . ?
C22 N8 C18 C19 -1.3(6) . . . . ?
Cu2 N8 C18 C19 179.1(4) . . . . ?
C22 N8 C18 C17 176.8(4) . . . . ?
Cu2 N8 C18 C17 -2.8(5) . . . . ?
N5 C17 C18 N8 23.5(5) . . . . ?
N5 C17 C18 C19 -158.4(4) . . . . ?
N8 C18 C19 C20 1.6(7) . . . . ?
C17 C18 C19 C20 -176.4(4) . . . . ?
C18 C19 C20 C21 -1.6(7) . . . . ?
C19 C20 C21 C22 1.4(7) . . . . ?
C18 N8 C22 C21 1.1(7) . . . . ?
Cu2 N8 C22 C21 -179.4(3) . . . . ?
C20 C21 C22 N8 -1.2(7) . . . . ?

_refine_diff_density_max         0.607
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.085


####################################################################### 
# 
# 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 2118647'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H23 N5'
_chemical_formula_sum            'C13 H23 N5'
_chemical_formula_weight         249.36

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      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                   7.7101(15)
_cell_length_b                   8.2333(16)
_cell_length_c                   21.676(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.89(3)
_cell_angle_gamma                90
_cell_volume                     1371.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14675
_cell_measurement_theta_min      3.38
_cell_measurement_theta_max      33.12

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3419
_exptl_absorpt_correction_T_max  0.9907
_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       '4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'

_diffrn_detector                 'Hybrid Pixel Counting Detector'
_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      
; 1762 frames, detector distance = 80 mm
;

_diffrn_reflns_number            13904
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.383
_diffrn_reflns_theta_max         33.108
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4924
_reflns_number_gt                4276
_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    'SHELXS-97 (Sheldrick, 1990)'
_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 1.77, 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)+(0.0654P)²+0.7411P] 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         4924
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1520
_refine_ls_wR_factor_gt          0.1410
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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 0.20462(17) 0.11431(15) 0.49309(5) 0.0235(2) Uani 1 1 d . . . . .
H1 H 0.141228 0.046370 0.518553 0.028 Uiso 1 1 calc R U . . .
C2 C 0.36829(16) 0.16260(15) 0.51618(5) 0.0232(2) Uani 1 1 d . . . . .
H2 H 0.413664 0.128908 0.556266 0.028 Uiso 1 1 calc R U . . .
C3 C 0.46822(15) 0.26239(14) 0.47998(5) 0.0202(2) Uani 1 1 d . . . . .
C4 C 0.38901(14) 0.30478(13) 0.42093(5) 0.01803(19) Uani 1 1 d . . . . .
H4 H 0.450071 0.370177 0.393882 0.022 Uiso 1 1 calc R U . . .
C5 C 0.22295(14) 0.25112(13) 0.40260(4) 0.01660(18) Uani 1 1 d . . . . .
C6 C 0.74070(17) 0.40295(18) 0.46208(6) 0.0290(3) Uani 1 1 d . . . . .
H6A H 0.801434 0.324818 0.437464 0.044 Uiso 1 1 calc R U . . .
H6B H 0.826177 0.466834 0.487853 0.044 Uiso 1 1 calc R U . . .
H6C H 0.670068 0.475656 0.434349 0.044 Uiso 1 1 calc R U . . .
C7 C 0.7009(2) 0.27657(18) 0.56358(7) 0.0346(3) Uani 1 1 d . . . . .
H7A H 0.724794 0.159755 0.566307 0.052 Uiso 1 1 calc R U . . .
H7B H 0.617277 0.305969 0.593289 0.052 Uiso 1 1 calc R U . . .
H7C H 0.809409 0.337018 0.573129 0.052 Uiso 1 1 calc R U . . .
C8 C 0.13232(13) 0.29848(13) 0.34044(5) 0.01713(18) Uani 1 1 d . . . . .
H8A H 0.107712 0.199213 0.315444 0.021 Uiso 1 1 calc R U . . .
H8B H 0.019582 0.350415 0.347048 0.021 Uiso 1 1 calc R U . . .
C9 C 0.22694(13) 0.39679(12) 0.24690(5) 0.01587(18) Uani 1 1 d . . . . .
C10 C 0.50364(15) 0.53743(15) 0.25214(6) 0.0243(2) Uani 1 1 d . . . . .
H10A H 0.593408 0.569090 0.225074 0.036 Uiso 1 1 calc R U . . .
H10B H 0.550530 0.454682 0.281492 0.036 Uiso 1 1 calc R U . . .
H10C H 0.467763 0.632742 0.274962 0.036 Uiso 1 1 calc R U . . .
C11 C 0.29672(15) 0.57709(14) 0.16278(5) 0.0211(2) Uani 1 1 d . . . . .
H11A H 0.384779 0.577337 0.132740 0.032 Uiso 1 1 calc R U . . .
H11B H 0.280679 0.687870 0.177823 0.032 Uiso 1 1 calc R U . . .
H11C H 0.186232 0.536631 0.142860 0.032 Uiso 1 1 calc R U . . .
N12 N 0.62891(15) 0.31649(15) 0.50137(5) 0.0297(2) Uani 1 1 d . . . . .
N13 N 0.12719(13) 0.15562(13) 0.43731(4) 0.02096(19) Uani 1 1 d . . . . .
N14 N 0.23476(12) 0.40889(11) 0.30636(4) 0.01701(17) Uani 1 1 d . . . . .
N15 N 0.35411(12) 0.47179(12) 0.21489(4) 0.01884(18) Uani 1 1 d . . . . .
N16 N 0.10469(12) 0.30542(12) 0.21078(4) 0.01821(18) Uani 1 1 d . . . . .
C17 C 0.14609(16) 0.22836(15) 0.15364(5) 0.0229(2) Uani 1 1 d . . . . .
H17A H 0.102399 0.295544 0.118356 0.034 Uiso 1 1 calc R U . . .
H17B H 0.091248 0.120992 0.150257 0.034 Uiso 1 1 calc R U . . .
H17C H 0.272584 0.216519 0.153714 0.034 Uiso 1 1 calc R U . . .
C18 C -0.07969(14) 0.33495(15) 0.21482(5) 0.0206(2) Uani 1 1 d . . . . .
H18A H -0.126056 0.398147 0.178807 0.031 Uiso 1 1 calc R U . . .
H18B H -0.096120 0.395671 0.252772 0.031 Uiso 1 1 calc R U . . .
H18C H -0.141306 0.230966 0.215617 0.031 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 N13 1.3456(15) . ?
C1 C2 1.3760(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.4097(17) . ?
C2 H2 0.9500 . ?
C3 N12 1.3603(16) . ?
C3 C4 1.4142(15) . ?
C4 C5 1.3804(15) . ?
C4 H4 0.9500 . ?
C5 N13 1.3507(14) . ?
C5 C8 1.5150(15) . ?
C6 N12 1.4492(18) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 N12 1.4515(17) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N14 1.4475(14) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N14 1.2891(13) . ?
C9 N15 1.3929(14) . ?
C9 N16 1.3933(13) . ?
C10 N15 1.4542(15) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 N15 1.4621(14) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N16 C17 1.4512(14) . ?
N16 C18 1.4522(14) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
N13 C1 C2 125.22(11) . . ?
N13 C1 H1 117.4 . . ?
C2 C1 H1 117.4 . . ?
C1 C2 C3 119.58(10) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
N12 C3 C2 121.75(10) . . ?
N12 C3 C4 122.56(11) . . ?
C2 C3 C4 115.67(10) . . ?
C5 C4 C3 120.00(10) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
N13 C5 C4 124.30(9) . . ?
N13 C5 C8 114.38(9) . . ?
C4 C5 C8 121.32(9) . . ?
N12 C6 H6A 109.5 . . ?
N12 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N12 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N12 C7 H7A 109.5 . . ?
N12 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N12 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N14 C8 C5 112.65(9) . . ?
N14 C8 H8A 109.1 . . ?
C5 C8 H8A 109.1 . . ?
N14 C8 H8B 109.1 . . ?
C5 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N14 C9 N15 119.27(9) . . ?
N14 C9 N16 125.12(10) . . ?
N15 C9 N16 115.51(9) . . ?
N15 C10 H10A 109.5 . . ?
N15 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N15 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N15 C11 H11A 109.5 . . ?
N15 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N15 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 N12 C6 122.04(10) . . ?
C3 N12 C7 120.51(12) . . ?
C6 N12 C7 117.23(11) . . ?
C1 N13 C5 115.21(10) . . ?
C9 N14 C8 118.73(9) . . ?
C9 N15 C10 116.52(9) . . ?
C9 N15 C11 117.91(9) . . ?
C10 N15 C11 112.46(9) . . ?
C9 N16 C17 121.88(9) . . ?
C9 N16 C18 119.64(9) . . ?
C17 N16 C18 114.35(9) . . ?
N16 C17 H17A 109.5 . . ?
N16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N16 C18 H18A 109.5 . . ?
N16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
N13 C1 C2 C3 -0.52(19) . . . . ?
C1 C2 C3 N12 178.38(12) . . . . ?
C1 C2 C3 C4 -0.34(16) . . . . ?
N12 C3 C4 C5 -177.59(11) . . . . ?
C2 C3 C4 C5 1.12(16) . . . . ?
C3 C4 C5 N13 -1.17(17) . . . . ?
C3 C4 C5 C8 178.15(10) . . . . ?
N13 C5 C8 N14 176.36(9) . . . . ?
C4 C5 C8 N14 -3.02(14) . . . . ?
C2 C3 N12 C6 172.63(12) . . . . ?
C4 C3 N12 C6 -8.74(19) . . . . ?
C2 C3 N12 C7 -1.87(19) . . . . ?
C4 C3 N12 C7 176.76(12) . . . . ?
C2 C1 N13 C5 0.54(18) . . . . ?
C4 C5 N13 C1 0.31(16) . . . . ?
C8 C5 N13 C1 -179.05(10) . . . . ?
N15 C9 N14 C8 -164.05(9) . . . . ?
N16 C9 N14 C8 12.12(16) . . . . ?
C5 C8 N14 C9 145.01(10) . . . . ?
N14 C9 N15 C10 9.59(15) . . . . ?
N16 C9 N15 C10 -166.95(10) . . . . ?
N14 C9 N15 C11 -128.80(11) . . . . ?
N16 C9 N15 C11 54.67(13) . . . . ?
N14 C9 N16 C17 -147.91(11) . . . . ?
N15 C9 N16 C17 28.40(15) . . . . ?
N14 C9 N16 C18 56.23(15) . . . . ?
N15 C9 N16 C18 -127.46(10) . . . . ?

_refine_diff_density_max         0.417
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.058


####################################################################### 
# 
# 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-I
_database_code_depnum_ccdc_archive 'CCDC 2118642'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-07-28 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         'C32 H46 Cu N10, C H2 Cl2, Br [+ THF]'
_chemical_formula_sum            'C33 H48 Br Cl2 Cu N10 [+ THF]'
_chemical_formula_weight         799.16

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.531(2)
_cell_length_b                   14.073(3)
_cell_length_c                   25.526(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4142.5(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    21194
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      30.41

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             1656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.655
_shelx_estimated_absorpt_T_min   0.755
_shelx_estimated_absorpt_T_max   0.801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4205
_exptl_absorpt_correction_T_max  0.8343
_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_type  'STOE STADIVARI'

_diffrn_detector                 'Hybrid Pixel Counting Detector'
_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      
; 1793 frames, detector distance = 80 mm
;

_diffrn_reflns_number            22376
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.895
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             7538
_reflns_number_gt                6601
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.979

_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 1.31.131.0 (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)+24.2836P] 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_abs_structure_details 
;
 Flack x determined using 2392 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7538
_refine_ls_number_parameters     436
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0659
_refine_ls_wR_factor_ref         0.1359
_refine_ls_wR_factor_gt          0.1250
_refine_ls_goodness_of_fit_ref   1.256
_refine_ls_restrained_S_all      1.256
_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 0.49403(9) 0.38242(6) 0.77282(4) 0.0252(2) Uani 1 1 d . . . . .
Cu1 Cu -0.01765(10) 0.23044(8) 0.74538(4) 0.0196(3) Uani 1 1 d . . . . .
N1 N 0.0792(7) 0.1403(5) 0.7935(3) 0.0196(18) Uani 1 1 d . . . . .
C1 C 0.1905(8) 0.1328(6) 0.7846(4) 0.019(2) Uani 1 1 d . . . . .
N2 N 0.2747(7) 0.1677(6) 0.8166(3) 0.0223(19) Uani 1 1 d . . . . .
C2 C 0.2525(9) 0.2461(8) 0.8521(4) 0.029(3) Uani 1 1 d . . . . .
H2A H 0.316084 0.292135 0.849769 0.043 Uiso 1 1 calc R U . . .
H2B H 0.247042 0.222013 0.888020 0.043 Uiso 1 1 calc R U . . .
H2C H 0.179483 0.277089 0.842446 0.043 Uiso 1 1 calc R U . . .
N3 N 0.2264(7) 0.0919(6) 0.7396(3) 0.0224(18) Uani 1 1 d . . . . .
C3 C 0.3884(8) 0.1232(8) 0.8231(4) 0.026(2) Uani 1 1 d . . . . .
H3A H 0.397571 0.102330 0.859491 0.039 Uiso 1 1 calc R U . . .
H3B H 0.449247 0.169262 0.814504 0.039 Uiso 1 1 calc R U . . .
H3C H 0.394595 0.068247 0.799694 0.039 Uiso 1 1 calc R U . . .
N4 N -0.1132(6) 0.2415(6) 0.8100(3) 0.0207(18) Uani 1 1 d . . . . .
C4 C 0.3211(9) 0.1282(8) 0.7083(5) 0.032(3) Uani 1 1 d . . . . .
H4A H 0.374932 0.076394 0.700103 0.047 Uiso 1 1 calc R U . . .
H4B H 0.362021 0.177828 0.727835 0.047 Uiso 1 1 calc R U . . .
H4C H 0.290444 0.154929 0.675628 0.047 Uiso 1 1 calc R U . . .
N5 N -0.3120(7) 0.2234(7) 0.9487(3) 0.028(2) Uani 1 1 d . . . . .
C5 C 0.1437(9) 0.0358(8) 0.7092(4) 0.028(3) Uani 1 1 d . . . . .
H5A H 0.185969 -0.006788 0.685525 0.042 Uiso 1 1 calc R U . . .
H5B H 0.094269 0.078383 0.688605 0.042 Uiso 1 1 calc R U . . .
H5C H 0.095498 -0.001921 0.732990 0.042 Uiso 1 1 calc R U . . .
C6 C 0.0312(7) 0.1371(6) 0.8436(3) 0.017(2) Uani 1 1 d . . . . .
C7 C 0.0734(9) 0.0828(7) 0.8843(4) 0.024(2) Uani 1 1 d . . . . .
H7 H 0.145883 0.051432 0.880730 0.028 Uiso 1 1 calc R U . . .
C8 C 0.0102(10) 0.0737(7) 0.9307(4) 0.028(2) Uani 1 1 d . . . . .
H8 H 0.039867 0.034634 0.957950 0.033 Uiso 1 1 calc R U . . .
C9 C -0.0926(8) 0.1194(8) 0.9380(4) 0.027(2) Uani 1 1 d . . . . .
H9 H -0.134719 0.110524 0.969609 0.033 Uiso 1 1 calc R U . . .
C10 C -0.1367(8) 0.1795(7) 0.8988(4) 0.020(2) Uani 1 1 d . . . . .
C11 C -0.0751(8) 0.1876(7) 0.8515(3) 0.018(2) Uani 1 1 d . . . . .
C12 C -0.2453(8) 0.2320(7) 0.9029(4) 0.024(2) Uani 1 1 d . . . . .
C13 C -0.2833(9) 0.2799(8) 0.8600(4) 0.026(2) Uani 1 1 d . . . . .
H13 H -0.356502 0.310934 0.860639 0.031 Uiso 1 1 calc R U . . .
C14 C -0.2145(8) 0.2835(7) 0.8150(4) 0.021(2) Uani 1 1 d . . . . .
H14 H -0.242954 0.318639 0.785916 0.025 Uiso 1 1 calc R U . . .
C15 C -0.4338(9) 0.2501(9) 0.9458(4) 0.037(3) Uani 1 1 d . . . . .
H15A H -0.475640 0.222579 0.975566 0.055 Uiso 1 1 calc R U . . .
H15B H -0.467042 0.226318 0.913026 0.055 Uiso 1 1 calc R U . . .
H15C H -0.440559 0.319527 0.946888 0.055 Uiso 1 1 calc R U . . .
C16 C -0.2619(12) 0.2505(16) 0.9988(5) 0.055(4) Uani 1 1 d . . . . .
H16A H -0.274366 0.199449 1.024270 0.083 Uiso 1 1 calc R U . . .
H16B H -0.299042 0.308855 1.011311 0.083 Uiso 1 1 calc R U . . .
H16C H -0.178524 0.261450 0.994479 0.083 Uiso 1 1 calc R U . . .
N21 N -0.1082(6) 0.2089(5) 0.6757(3) 0.0166(17) Uani 1 1 d . . . . .
C21 C -0.2217(8) 0.2041(6) 0.6793(3) 0.0151(19) Uani 1 1 d . . . . .
N22 N -0.2963(7) 0.2746(6) 0.6657(3) 0.0213(18) Uani 1 1 d . . . . .
C22 C -0.2609(10) 0.3714(8) 0.6651(5) 0.031(3) Uani 1 1 d . . . . .
H22A H -0.187991 0.378121 0.684426 0.046 Uiso 1 1 calc R U . . .
H22B H -0.320826 0.410646 0.681593 0.046 Uiso 1 1 calc R U . . .
H22C H -0.249590 0.392052 0.628774 0.046 Uiso 1 1 calc R U . . .
N23 N -0.2693(7) 0.1249(6) 0.7020(3) 0.0205(18) Uani 1 1 d . . . . .
C23 C -0.4128(8) 0.2570(8) 0.6464(4) 0.028(2) Uani 1 1 d . . . . .
H23A H -0.429277 0.188732 0.647925 0.042 Uiso 1 1 calc R U . . .
H23B H -0.418837 0.278949 0.610053 0.042 Uiso 1 1 calc R U . . .
H23C H -0.468826 0.291381 0.668136 0.042 Uiso 1 1 calc R U . . .
N24 N 0.0856(7) 0.3025(5) 0.6973(3) 0.0161(16) Uani 1 1 d . . . . .
C24 C -0.3618(8) 0.1307(7) 0.7415(4) 0.023(2) Uani 1 1 d . . . . .
H24A H -0.396571 0.194203 0.740633 0.034 Uiso 1 1 calc R U . . .
H24B H -0.329126 0.118746 0.776292 0.034 Uiso 1 1 calc R U . . .
H24C H -0.421320 0.083005 0.733775 0.034 Uiso 1 1 calc R U . . .
N25 N 0.2982(7) 0.4284(6) 0.5808(3) 0.027(2) Uani 1 1 d . . . . .
C25 C -0.1965(9) 0.0402(8) 0.7087(4) 0.029(3) Uani 1 1 d . . . . .
H25A H -0.145608 0.033130 0.678173 0.044 Uiso 1 1 calc R U . . .
H25B H -0.245985 -0.016116 0.711895 0.044 Uiso 1 1 calc R U . . .
H25C H -0.149309 0.047034 0.740374 0.044 Uiso 1 1 calc R U . . .
C26 C -0.0559(8) 0.2583(7) 0.6339(3) 0.019(2) Uani 1 1 d . . . . .
C27 C -0.0969(9) 0.2600(7) 0.5832(4) 0.025(2) Uani 1 1 d . . . . .
H27 H -0.168097 0.229708 0.574786 0.030 Uiso 1 1 calc R U . . .
C28 C -0.0329(8) 0.3066(8) 0.5440(3) 0.025(2) Uani 1 1 d . . . . .
H28 H -0.063962 0.309907 0.509545 0.030 Uiso 1 1 calc R U . . .
C29 C 0.0721(9) 0.3472(8) 0.5538(4) 0.026(2) Uani 1 1 d . . . . .
H29 H 0.113699 0.376554 0.526056 0.032 Uiso 1 1 calc R U . . .
C30 C 0.1193(8) 0.3461(7) 0.6043(4) 0.019(2) Uani 1 1 d . . . . .
C31 C 0.0531(8) 0.3034(6) 0.6455(4) 0.017(2) Uani 1 1 d . . . . .
C32 C 0.2287(8) 0.3870(7) 0.6195(4) 0.0179(19) Uani 1 1 d . . . . .
C33 C 0.2582(8) 0.3891(7) 0.6714(4) 0.021(2) Uani 1 1 d . . . . .
H33 H 0.327498 0.419664 0.682324 0.025 Uiso 1 1 calc R U . . .
C34 C 0.1849(8) 0.3453(7) 0.7085(4) 0.022(2) Uani 1 1 d . . . . .
H34 H 0.208486 0.346628 0.744156 0.027 Uiso 1 1 calc R U . . .
C35 C 0.3444(9) 0.3629(8) 0.5414(4) 0.033(3) Uani 1 1 d . . . . .
H35A H 0.358689 0.397387 0.508733 0.049 Uiso 1 1 calc R U . . .
H35B H 0.288063 0.311979 0.535101 0.049 Uiso 1 1 calc R U . . .
H35C H 0.417173 0.335344 0.554147 0.049 Uiso 1 1 calc R U . . .
C36 C 0.3876(9) 0.4934(7) 0.5991(4) 0.029(3) Uani 1 1 d . . . . .
H36A H 0.422236 0.526227 0.569118 0.043 Uiso 1 1 calc R U . . .
H36B H 0.447635 0.457588 0.617768 0.043 Uiso 1 1 calc R U . . .
H36C H 0.352936 0.540194 0.622887 0.043 Uiso 1 1 calc R U . . .
C40 C 1.0837(11) 0.5121(9) 0.3933(5) 0.042(3) Uani 1 1 d . . . . .
H40A H 1.094543 0.482813 0.358355 0.051 Uiso 1 1 calc R U . . .
H40B H 1.073309 0.581349 0.388252 0.051 Uiso 1 1 calc R U . . .
Cl41 Cl 1.2058(3) 0.4921(5) 0.43103(14) 0.0880(16) Uani 1 1 d . . . . .
Cl42 Cl 0.9586(3) 0.4644(2) 0.42290(11) 0.0413(7) 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 N24 1.987(8) . ?
Cu1 N4 1.990(8) . ?
Cu1 N21 2.085(8) . ?
Cu1 N1 2.090(8) . ?
N1 C1 1.307(12) . ?
N1 C6 1.394(11) . ?
C1 N3 1.350(12) . ?
C1 N2 1.360(12) . ?
N2 C2 1.451(13) . ?
N2 C3 1.462(12) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N3 C4 1.446(13) . ?
N3 C5 1.462(13) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
N4 C14 1.315(12) . ?
N4 C11 1.375(12) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N5 C12 1.405(12) . ?
N5 C16 1.452(16) . ?
N5 C15 1.455(13) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.378(13) . ?
C6 C11 1.431(12) . ?
C7 C8 1.397(14) . ?
C7 H7 0.9500 . ?
C8 C9 1.362(15) . ?
C8 H8 0.9500 . ?
C9 C10 1.407(14) . ?
C9 H9 0.9500 . ?
C10 C11 1.404(13) . ?
C10 C12 1.458(13) . ?
C12 C13 1.359(14) . ?
C13 C14 1.398(14) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N21 C21 1.313(12) . ?
N21 C26 1.409(12) . ?
C21 N22 1.358(12) . ?
C21 N23 1.372(12) . ?
N22 C22 1.422(13) . ?
N22 C23 1.452(12) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
N23 C25 1.468(13) . ?
N23 C24 1.468(12) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
N24 C34 1.325(12) . ?
N24 C31 1.375(12) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N25 C32 1.400(12) . ?
N25 C36 1.455(12) . ?
N25 C35 1.464(14) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.378(13) . ?
C26 C31 1.438(12) . ?
C27 C28 1.406(13) . ?
C27 H27 0.9500 . ?
C28 C29 1.362(14) . ?
C28 H28 0.9500 . ?
C29 C30 1.399(14) . ?
C29 H29 0.9500 . ?
C30 C31 1.433(13) . ?
C30 C32 1.440(13) . ?
C32 C33 1.367(14) . ?
C33 C34 1.412(14) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C40 Cl41 1.729(13) . ?
C40 Cl42 1.761(12) . ?
C40 H40A 0.9900 . ?
C40 H40B 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
N24 Cu1 N4 143.4(3) . . ?
N24 Cu1 N21 81.2(3) . . ?
N4 Cu1 N21 116.2(3) . . ?
N24 Cu1 N1 110.6(3) . . ?
N4 Cu1 N1 81.7(3) . . ?
N21 Cu1 N1 132.9(3) . . ?
C1 N1 C6 123.2(8) . . ?
C1 N1 Cu1 118.1(6) . . ?
C6 N1 Cu1 110.2(6) . . ?
N1 C1 N3 118.9(9) . . ?
N1 C1 N2 124.6(9) . . ?
N3 C1 N2 116.4(8) . . ?
C1 N2 C2 121.5(8) . . ?
C1 N2 C3 123.7(8) . . ?
C2 N2 C3 114.3(8) . . ?
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 123.5(9) . . ?
C1 N3 C5 118.8(8) . . ?
C4 N3 C5 112.9(8) . . ?
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 . . ?
C14 N4 C11 117.2(8) . . ?
C14 N4 Cu1 127.4(7) . . ?
C11 N4 Cu1 114.7(6) . . ?
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 . . ?
C12 N5 C16 119.4(9) . . ?
C12 N5 C15 117.6(9) . . ?
C16 N5 C15 111.2(9) . . ?
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 . . ?
C7 C6 N1 124.7(8) . . ?
C7 C6 C11 118.1(8) . . ?
N1 C6 C11 117.0(8) . . ?
C6 C7 C8 120.4(9) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 121.8(9) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 120.1(9) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 118.5(9) . . ?
C11 C10 C12 117.2(9) . . ?
C9 C10 C12 124.3(9) . . ?
N4 C11 C10 123.0(9) . . ?
N4 C11 C6 116.0(8) . . ?
C10 C11 C6 121.0(9) . . ?
C13 C12 N5 122.5(9) . . ?
C13 C12 C10 118.0(9) . . ?
N5 C12 C10 119.2(9) . . ?
C12 C13 C14 119.8(9) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
N4 C14 C13 124.6(9) . . ?
N4 C14 H14 117.7 . . ?
C13 C14 H14 117.7 . . ?
N5 C15 H15A 109.5 . . ?
N5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N5 C16 H16A 109.5 . . ?
N5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C21 N21 C26 120.3(8) . . ?
C21 N21 Cu1 116.6(6) . . ?
C26 N21 Cu1 111.1(6) . . ?
N21 C21 N22 125.1(8) . . ?
N21 C21 N23 118.1(8) . . ?
N22 C21 N23 116.6(8) . . ?
C21 N22 C22 121.4(8) . . ?
C21 N22 C23 123.2(8) . . ?
C22 N22 C23 115.2(8) . . ?
N22 C22 H22A 109.5 . . ?
N22 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N22 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 N23 C25 118.7(8) . . ?
C21 N23 C24 122.4(8) . . ?
C25 N23 C24 112.4(8) . . ?
N22 C23 H23A 109.5 . . ?
N22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C34 N24 C31 116.0(8) . . ?
C34 N24 Cu1 128.1(7) . . ?
C31 N24 Cu1 115.8(6) . . ?
N23 C24 H24A 109.5 . . ?
N23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C32 N25 C36 116.1(8) . . ?
C32 N25 C35 115.5(8) . . ?
C36 N25 C35 111.1(8) . . ?
N23 C25 H25A 109.5 . . ?
N23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 N21 125.0(9) . . ?
C27 C26 C31 119.0(9) . . ?
N21 C26 C31 115.8(8) . . ?
C26 C27 C28 119.8(9) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C29 C28 C27 122.0(9) . . ?
C29 C28 H28 119.0 . . ?
C27 C28 H28 119.0 . . ?
C28 C29 C30 120.7(10) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C29 C30 C31 118.3(9) . . ?
C29 C30 C32 125.8(9) . . ?
C31 C30 C32 115.9(8) . . ?
N24 C31 C30 124.4(8) . . ?
N24 C31 C26 115.6(8) . . ?
C30 C31 C26 120.0(9) . . ?
C33 C32 N25 122.2(9) . . ?
C33 C32 C30 119.2(9) . . ?
N25 C32 C30 118.5(8) . . ?
C32 C33 C34 119.5(9) . . ?
C32 C33 H33 120.3 . . ?
C34 C33 H33 120.3 . . ?
N24 C34 C33 124.8(9) . . ?
N24 C34 H34 117.6 . . ?
C33 C34 H34 117.6 . . ?
N25 C35 H35A 109.5 . . ?
N25 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
N25 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N25 C36 H36A 109.5 . . ?
N25 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N25 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
Cl41 C40 Cl42 111.4(7) . . ?
Cl41 C40 H40A 109.3 . . ?
Cl42 C40 H40A 109.3 . . ?
Cl41 C40 H40B 109.3 . . ?
Cl42 C40 H40B 109.3 . . ?
H40A C40 H40B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C1 N3 148.4(9) . . . . ?
Cu1 N1 C1 N3 -66.8(10) . . . . ?
C6 N1 C1 N2 -34.9(14) . . . . ?
Cu1 N1 C1 N2 110.0(9) . . . . ?
N1 C1 N2 C2 -24.3(14) . . . . ?
N3 C1 N2 C2 152.6(9) . . . . ?
N1 C1 N2 C3 147.8(9) . . . . ?
N3 C1 N2 C3 -35.4(13) . . . . ?
N1 C1 N3 C4 138.0(9) . . . . ?
N2 C1 N3 C4 -39.1(13) . . . . ?
N1 C1 N3 C5 -15.8(13) . . . . ?
N2 C1 N3 C5 167.1(9) . . . . ?
C1 N1 C6 C7 -34.0(14) . . . . ?
Cu1 N1 C6 C7 178.8(8) . . . . ?
C1 N1 C6 C11 151.7(9) . . . . ?
Cu1 N1 C6 C11 4.4(10) . . . . ?
N1 C6 C7 C8 -170.9(9) . . . . ?
C11 C6 C7 C8 3.5(14) . . . . ?
C6 C7 C8 C9 -1.7(16) . . . . ?
C7 C8 C9 C10 -1.7(16) . . . . ?
C8 C9 C10 C11 3.0(15) . . . . ?
C8 C9 C10 C12 -179.5(10) . . . . ?
C14 N4 C11 C10 -3.0(14) . . . . ?
Cu1 N4 C11 C10 -174.3(7) . . . . ?
C14 N4 C11 C6 175.5(8) . . . . ?
Cu1 N4 C11 C6 4.3(10) . . . . ?
C9 C10 C11 N4 177.4(9) . . . . ?
C12 C10 C11 N4 -0.3(14) . . . . ?
C9 C10 C11 C6 -1.1(14) . . . . ?
C12 C10 C11 C6 -178.8(8) . . . . ?
C7 C6 C11 N4 179.3(9) . . . . ?
N1 C6 C11 N4 -5.9(12) . . . . ?
C7 C6 C11 C10 -2.1(14) . . . . ?
N1 C6 C11 C10 172.7(9) . . . . ?
C16 N5 C12 C13 -127.1(14) . . . . ?
C15 N5 C12 C13 12.6(15) . . . . ?
C16 N5 C12 C10 59.6(16) . . . . ?
C15 N5 C12 C10 -160.7(10) . . . . ?
C11 C10 C12 C13 4.1(14) . . . . ?
C9 C10 C12 C13 -173.4(10) . . . . ?
C11 C10 C12 N5 177.7(9) . . . . ?
C9 C10 C12 N5 0.2(15) . . . . ?
N5 C12 C13 C14 -178.0(10) . . . . ?
C10 C12 C13 C14 -4.6(15) . . . . ?
C11 N4 C14 C13 2.6(15) . . . . ?
Cu1 N4 C14 C13 172.6(8) . . . . ?
C12 C13 C14 N4 1.3(17) . . . . ?
C26 N21 C21 N22 -35.7(13) . . . . ?
Cu1 N21 C21 N22 103.6(9) . . . . ?
C26 N21 C21 N23 149.3(8) . . . . ?
Cu1 N21 C21 N23 -71.3(9) . . . . ?
N21 C21 N22 C22 -24.4(14) . . . . ?
N23 C21 N22 C22 150.6(9) . . . . ?
N21 C21 N22 C23 149.8(9) . . . . ?
N23 C21 N22 C23 -35.2(13) . . . . ?
N21 C21 N23 C25 -15.6(13) . . . . ?
N22 C21 N23 C25 169.0(9) . . . . ?
N21 C21 N23 C24 133.9(9) . . . . ?
N22 C21 N23 C24 -41.5(12) . . . . ?
C21 N21 C26 C27 -37.1(14) . . . . ?
Cu1 N21 C26 C27 -178.4(8) . . . . ?
C21 N21 C26 C31 148.0(8) . . . . ?
Cu1 N21 C26 C31 6.6(9) . . . . ?
N21 C26 C27 C28 -175.8(9) . . . . ?
C31 C26 C27 C28 -0.9(14) . . . . ?
C26 C27 C28 C29 3.0(16) . . . . ?
C27 C28 C29 C30 -1.7(16) . . . . ?
C28 C29 C30 C31 -1.5(15) . . . . ?
C28 C29 C30 C32 -179.6(10) . . . . ?
C34 N24 C31 C30 0.5(13) . . . . ?
Cu1 N24 C31 C30 -176.0(7) . . . . ?
C34 N24 C31 C26 -178.9(8) . . . . ?
Cu1 N24 C31 C26 4.7(10) . . . . ?
C29 C30 C31 N24 -175.9(9) . . . . ?
C32 C30 C31 N24 2.4(14) . . . . ?
C29 C30 C31 C26 3.5(14) . . . . ?
C32 C30 C31 C26 -178.2(8) . . . . ?
C27 C26 C31 N24 177.1(9) . . . . ?
N21 C26 C31 N24 -7.6(11) . . . . ?
C27 C26 C31 C30 -2.3(13) . . . . ?
N21 C26 C31 C30 173.0(8) . . . . ?
C36 N25 C32 C33 -14.7(14) . . . . ?
C35 N25 C32 C33 117.9(11) . . . . ?
C36 N25 C32 C30 161.5(9) . . . . ?
C35 N25 C32 C30 -65.9(12) . . . . ?
C29 C30 C32 C33 173.3(10) . . . . ?
C31 C30 C32 C33 -4.8(14) . . . . ?
C29 C30 C32 N25 -3.0(15) . . . . ?
C31 C30 C32 N25 178.9(8) . . . . ?
N25 C32 C33 C34 -179.5(9) . . . . ?
C30 C32 C33 C34 4.4(14) . . . . ?
C31 N24 C34 C33 -1.1(14) . . . . ?
Cu1 N24 C34 C33 174.8(7) . . . . ?
C32 C33 C34 N24 -1.4(16) . . . . ?

_refine_diff_density_max         0.844
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.107



####################################################################### 
# 
# 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 2118641'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-07-28 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         'C32 H46 Cu N10, 2(Br) [+ 2 (C4 H10 O)]'
_chemical_formula_sum            'C32 H46 Cu N10 Br2 [+ C8 H20 O2]'
_chemical_formula_weight         794.15

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

# start Validation Reply Form
_vrf_GOODF01_h21_a10a_a_sq       
;
PROBLEM: The least squares goodness of fit parameter lies
RESPONSE: The best possible crystal of the compound has been utilised 
for the data collection at low temperature.
But the overall quality of the data set is poor due to the 
crystal quality.
;

_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                   11.581(2)
_cell_length_b                   13.967(3)
_cell_length_c                   14.017(3)
_cell_angle_alpha                72.17(3)
_cell_angle_beta                 85.97(3)
_cell_angle_gamma                73.20(3)
_cell_volume                     2065.8(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1051
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      18.44

_exptl_crystal_description       rod
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             814
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    2.495
_shelx_estimated_absorpt_T_min   0.307
_shelx_estimated_absorpt_T_max   0.706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3792
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS-2008/1
_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            17230
_diffrn_reflns_av_unetI/netI     0.2475
_diffrn_reflns_av_R_equivalents  0.1633
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.837
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7618
_reflns_number_gt                3209
_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       'SMART (Bruker, 2001)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT-PLUS (Bruker, 2009)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    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)+(0.0492P)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         7618
_refine_ls_number_parameters     418
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1443
_refine_ls_R_factor_gt           0.0686
_refine_ls_wR_factor_ref         0.1599
_refine_ls_wR_factor_gt          0.1407
_refine_ls_goodness_of_fit_ref   0.788
_refine_ls_restrained_S_all      0.788
_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
Br1 Br 0.75452(8) 1.04861(7) 0.48931(6) 0.0353(3) Uani 1 1 d . . . . .
Cu1 Cu 0.77851(9) 0.81482(7) 0.61214(7) 0.0297(3) Uani 1 1 d . . . . .
N1 N 0.7188(5) 0.7172(5) 0.5668(4) 0.0253(16) Uani 1 1 d . . . . .
C1 C 0.6116(8) 0.7000(5) 0.5883(5) 0.0249(19) Uani 1 1 d . . . . .
Br2 Br 0.43968(9) 0.41596(7) 0.76162(7) 0.0516(3) Uani 1 1 d . . . . .
N2 N 0.5818(6) 0.6707(4) 0.6856(5) 0.0280(16) Uani 1 1 d . . . . .
C2 C 0.5255(7) 0.7848(6) 0.4189(5) 0.030(2) Uani 1 1 d . . . . .
H2A H 0.584277 0.824102 0.415151 0.045 Uiso 1 1 calc R U . . .
H2B H 0.444197 0.833557 0.405911 0.045 Uiso 1 1 calc R U . . .
H2C H 0.544000 0.747091 0.368668 0.045 Uiso 1 1 calc R U . . .
N3 N 0.5314(6) 0.7102(5) 0.5184(4) 0.0262(16) Uani 1 1 d . . . . .
C3 C 0.6736(8) 0.6237(6) 0.7641(6) 0.038(2) Uani 1 1 d . . . . .
H3A H 0.752642 0.602372 0.734695 0.057 Uiso 1 1 calc R U . . .
H3B H 0.656096 0.562200 0.812087 0.057 Uiso 1 1 calc R U . . .
H3C H 0.674401 0.674828 0.798685 0.057 Uiso 1 1 calc R U . . .
N4 N 0.9073(5) 0.7818(4) 0.5225(4) 0.0236(15) Uani 1 1 d . . . . .
C4 C 0.4484(7) 0.6470(6) 0.5341(5) 0.032(2) Uani 1 1 d . . . . .
H4A H 0.469551 0.589947 0.597065 0.048 Uiso 1 1 calc R U . . .
H4B H 0.453343 0.617482 0.478380 0.048 Uiso 1 1 calc R U . . .
H4C H 0.365975 0.690711 0.537557 0.048 Uiso 1 1 calc R U . . .
N5 N 1.1674(5) 0.7012(5) 0.3170(4) 0.0262(16) Uani 1 1 d . . . . .
C5 C 0.4551(7) 0.6977(6) 0.7185(6) 0.032(2) Uani 1 1 d . . . . .
H5A H 0.402416 0.743144 0.660789 0.048 Uiso 1 1 calc R U . . .
H5B H 0.448447 0.734455 0.768951 0.048 Uiso 1 1 calc R U . . .
H5C H 0.430569 0.633399 0.747597 0.048 Uiso 1 1 calc R U . . .
N6 N 0.8658(6) 0.8169(4) 0.7273(4) 0.0198(15) Uani 1 1 d . . . . .
C6 C 0.7892(7) 0.6823(6) 0.4923(5) 0.0246(19) Uani 1 1 d . . . . .
N7 N 1.0470(6) 0.6934(5) 0.7341(4) 0.0257(16) Uani 1 1 d . . . . .
C7 C 0.7689(7) 0.6209(6) 0.4410(6) 0.034(2) Uani 1 1 d . . . . .
H7 H 0.700341 0.594864 0.454783 0.040 Uiso 1 1 calc R U . . .
N8 N 1.0477(6) 0.8521(4) 0.7456(4) 0.0242(15) Uani 1 1 d . . . . .
C8 C 0.8488(8) 0.5962(6) 0.3681(6) 0.036(2) Uani 1 1 d . . . . .
H8 H 0.832113 0.554233 0.331756 0.044 Uiso 1 1 calc R U . . .
N9 N 0.6400(6) 0.8838(4) 0.6750(4) 0.0223(15) Uani 1 1 d . . . . .
C9 C 0.9492(7) 0.6288(6) 0.3462(5) 0.029(2) Uani 1 1 d . . . . .
H9 H 0.999808 0.611959 0.293864 0.035 Uiso 1 1 calc R U . . .
N10 N 0.3694(6) 1.0703(5) 0.8069(4) 0.0283(16) Uani 1 1 d . . . . .
C10 C 0.9781(7) 0.6872(5) 0.4008(5) 0.0224(18) Uani 1 1 d . . . . .
C11 C 1.0810(7) 0.7254(6) 0.3822(5) 0.029(2) Uani 1 1 d . . . . .
C12 C 1.0856(7) 0.7985(5) 0.4325(5) 0.0227(18) Uani 1 1 d . . . . .
H12 H 1.149472 0.830456 0.420246 0.027 Uiso 1 1 calc R U . . .
C13 C 0.9976(7) 0.8227(6) 0.4986(5) 0.0264(19) Uani 1 1 d . . . . .
H13 H 1.002401 0.873121 0.529654 0.032 Uiso 1 1 calc R U . . .
C14 C 0.8950(7) 0.7172(5) 0.4711(5) 0.0248(19) Uani 1 1 d . . . . .
C15 C 1.2205(8) 0.5955(6) 0.3126(7) 0.051(3) Uani 1 1 d . . . . .
H15A H 1.220180 0.594785 0.242902 0.077 Uiso 1 1 calc R U . . .
H15B H 1.173543 0.549846 0.353223 0.077 Uiso 1 1 calc R U . . .
H15C H 1.303712 0.570048 0.338630 0.077 Uiso 1 1 calc R U . . .
C16 C 1.2498(7) 0.7655(6) 0.2824(6) 0.039(2) Uani 1 1 d . . . . .
H16A H 1.286848 0.754537 0.220063 0.059 Uiso 1 1 calc R U . . .
H16B H 1.312956 0.745648 0.333522 0.059 Uiso 1 1 calc R U . . .
H16C H 1.205265 0.839500 0.270102 0.059 Uiso 1 1 calc R U . . .
C17 C 0.9853(8) 0.7874(6) 0.7380(5) 0.0251(19) Uani 1 1 d . . . . .
C18 C 0.9896(7) 0.6077(6) 0.7597(6) 0.034(2) Uani 1 1 d . . . . .
H18A H 1.047497 0.542218 0.796916 0.051 Uiso 1 1 calc R U . . .
H18B H 0.963816 0.599863 0.698088 0.051 Uiso 1 1 calc R U . . .
H18C H 0.919277 0.623948 0.801208 0.051 Uiso 1 1 calc R U . . .
C19 C 1.0000(7) 0.9654(6) 0.7035(5) 0.034(2) Uani 1 1 d . . . . .
H19A H 1.061682 0.993690 0.662666 0.050 Uiso 1 1 calc R U . . .
H19B H 0.977652 0.997251 0.757892 0.050 Uiso 1 1 calc R U . . .
H19C H 0.928634 0.981465 0.661451 0.050 Uiso 1 1 calc R U . . .
C20 C 1.1653(7) 0.6679(6) 0.6926(6) 0.037(2) Uani 1 1 d . . . . .
H20A H 1.222773 0.618455 0.745580 0.055 Uiso 1 1 calc R U . . .
H20B H 1.190552 0.731987 0.664406 0.055 Uiso 1 1 calc R U . . .
H20C H 1.163165 0.636041 0.639730 0.055 Uiso 1 1 calc R U . . .
C21 C 1.1606(7) 0.8144(6) 0.8015(5) 0.032(2) Uani 1 1 d . . . . .
H21A H 1.152619 0.846120 0.855864 0.048 Uiso 1 1 calc R U . . .
H21B H 1.224520 0.833479 0.756648 0.048 Uiso 1 1 calc R U . . .
H21C H 1.181087 0.737933 0.829690 0.048 Uiso 1 1 calc R U . . .
C22 C 0.7917(7) 0.8767(5) 0.7823(5) 0.0210(18) Uani 1 1 d . . . . .
C23 C 0.8237(7) 0.8958(6) 0.8671(5) 0.030(2) Uani 1 1 d . . . . .
H23 H 0.905408 0.871163 0.889793 0.035 Uiso 1 1 calc R U . . .
C24 C 0.7363(8) 0.9506(6) 0.9183(6) 0.033(2) Uani 1 1 d . . . . .
H24 H 0.759943 0.962743 0.976084 0.040 Uiso 1 1 calc R U . . .
C25 C 0.6192(8) 0.9875(6) 0.8897(5) 0.030(2) Uani 1 1 d . . . . .
H25 H 0.562376 1.024397 0.927543 0.037 Uiso 1 1 calc R U . . .
C26 C 0.5799(7) 0.9717(5) 0.8032(5) 0.0234(19) Uani 1 1 d . . . . .
C27 C 0.4595(7) 1.0069(6) 0.7672(5) 0.027(2) Uani 1 1 d . . . . .
C28 C 0.4342(7) 0.9723(5) 0.6922(5) 0.0234(19) Uani 1 1 d . . . . .
H28 H 0.353199 0.988722 0.669992 0.028 Uiso 1 1 calc R U . . .
C29 C 0.5252(8) 0.9143(6) 0.6496(5) 0.028(2) Uani 1 1 d . . . . .
H29 H 0.503757 0.893704 0.596276 0.033 Uiso 1 1 calc R U . . .
C30 C 0.6697(7) 0.9135(5) 0.7543(5) 0.0220(19) Uani 1 1 d . . . . .
C31 C 0.3852(8) 1.1614(6) 0.8297(6) 0.039(2) Uani 1 1 d . . . . .
H31A H 0.371632 1.153645 0.901096 0.058 Uiso 1 1 calc R U . . .
H31B H 0.327115 1.225212 0.789741 0.058 Uiso 1 1 calc R U . . .
H31C H 0.467375 1.166319 0.813374 0.058 Uiso 1 1 calc R U . . .
C32 C 0.2450(7) 1.0858(7) 0.7824(6) 0.047(2) Uani 1 1 d . . . . .
H32A H 0.192998 1.108781 0.834072 0.070 Uiso 1 1 calc R U . . .
H32B H 0.234372 1.019709 0.779114 0.070 Uiso 1 1 calc R U . . .
H32C H 0.223128 1.139286 0.717296 0.070 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 N9 1.924(6) . ?
Cu1 N4 1.926(6) . ?
Cu1 N1 1.969(6) . ?
Cu1 N6 1.976(6) . ?
N1 C1 1.329(9) . ?
N1 C6 1.398(8) . ?
C1 N3 1.346(9) . ?
C1 N2 1.349(8) . ?
N2 C3 1.446(9) . ?
N2 C5 1.484(8) . ?
C2 N3 1.455(8) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N3 C4 1.447(9) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
N4 C13 1.307(8) . ?
N4 C14 1.357(8) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N5 C11 1.347(9) . ?
N5 C15 1.446(9) . ?
N5 C16 1.454(9) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
N6 C17 1.330(9) . ?
N6 C22 1.383(8) . ?
C6 C7 1.352(10) . ?
C6 C14 1.426(10) . ?
N7 C17 1.316(9) . ?
N7 C20 1.440(9) . ?
N7 C18 1.472(8) . ?
C7 C8 1.384(10) . ?
C7 H7 0.9500 . ?
N8 C17 1.341(9) . ?
N8 C21 1.446(9) . ?
N8 C19 1.459(9) . ?
C8 C9 1.351(10) . ?
C8 H8 0.9500 . ?
N9 C29 1.313(9) . ?
N9 C30 1.395(8) . ?
C9 C10 1.393(9) . ?
C9 H9 0.9500 . ?
N10 C27 1.367(9) . ?
N10 C32 1.443(9) . ?
N10 C31 1.465(8) . ?
C10 C14 1.398(9) . ?
C10 C11 1.418(10) . ?
C11 C12 1.421(9) . ?
C12 C13 1.368(9) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.390(9) . ?
C22 C30 1.397(10) . ?
C23 C24 1.383(10) . ?
C23 H23 0.9500 . ?
C24 C25 1.346(10) . ?
C24 H24 0.9500 . ?
C25 C26 1.423(10) . ?
C25 H25 0.9500 . ?
C26 C30 1.402(9) . ?
C26 C27 1.411(10) . ?
C27 C28 1.363(9) . ?
C28 C29 1.355(9) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 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
N9 Cu1 N4 164.7(2) . . ?
N9 Cu1 N1 103.0(3) . . ?
N4 Cu1 N1 82.3(2) . . ?
N9 Cu1 N6 83.0(3) . . ?
N4 Cu1 N6 102.4(2) . . ?
N1 Cu1 N6 139.8(2) . . ?
C1 N1 C6 120.8(6) . . ?
C1 N1 Cu1 124.8(5) . . ?
C6 N1 Cu1 113.2(5) . . ?
N1 C1 N3 123.5(6) . . ?
N1 C1 N2 118.1(7) . . ?
N3 C1 N2 118.4(7) . . ?
C1 N2 C3 121.0(7) . . ?
C1 N2 C5 122.2(7) . . ?
C3 N2 C5 116.3(6) . . ?
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 N3 C4 123.5(6) . . ?
C1 N3 C2 121.3(6) . . ?
C4 N3 C2 115.1(6) . . ?
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 . . ?
C13 N4 C14 116.9(6) . . ?
C13 N4 Cu1 127.2(5) . . ?
C14 N4 Cu1 115.5(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 . . ?
C11 N5 C15 122.9(6) . . ?
C11 N5 C16 119.6(6) . . ?
C15 N5 C16 111.8(6) . . ?
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 . . ?
C17 N6 C22 122.0(6) . . ?
C17 N6 Cu1 124.3(5) . . ?
C22 N6 Cu1 111.8(5) . . ?
C7 C6 N1 128.1(7) . . ?
C7 C6 C14 118.3(7) . . ?
N1 C6 C14 113.5(6) . . ?
C17 N7 C20 125.0(6) . . ?
C17 N7 C18 120.3(6) . . ?
C20 N7 C18 114.1(6) . . ?
C6 C7 C8 119.5(8) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C17 N8 C21 122.2(6) . . ?
C17 N8 C19 121.0(6) . . ?
C21 N8 C19 116.6(6) . . ?
C9 C8 C7 123.2(8) . . ?
C9 C8 H8 118.4 . . ?
C7 C8 H8 118.4 . . ?
C29 N9 C30 116.1(6) . . ?
C29 N9 Cu1 130.2(5) . . ?
C30 N9 Cu1 113.5(5) . . ?
C8 C9 C10 119.6(7) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C27 N10 C32 119.8(7) . . ?
C27 N10 C31 122.1(6) . . ?
C32 N10 C31 111.3(7) . . ?
C9 C10 C14 117.6(7) . . ?
C9 C10 C11 123.3(7) . . ?
C14 C10 C11 118.8(7) . . ?
N5 C11 C10 124.1(7) . . ?
N5 C11 C12 120.0(7) . . ?
C10 C11 C12 115.7(7) . . ?
C13 C12 C11 119.7(7) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
N4 C13 C12 125.1(7) . . ?
N4 C13 H13 117.4 . . ?
C12 C13 H13 117.4 . . ?
N4 C14 C10 123.3(7) . . ?
N4 C14 C6 115.2(7) . . ?
C10 C14 C6 121.5(6) . . ?
N5 C15 H15A 109.5 . . ?
N5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N5 C16 H16A 109.5 . . ?
N5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N7 C17 N6 119.5(7) . . ?
N7 C17 N8 117.7(7) . . ?
N6 C17 N8 122.7(7) . . ?
N7 C18 H18A 109.5 . . ?
N7 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N7 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 . . ?
N7 C20 H20A 109.5 . . ?
N7 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N7 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N8 C21 H21A 109.5 . . ?
N8 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N8 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N6 C22 C23 127.0(7) . . ?
N6 C22 C30 115.7(6) . . ?
C23 C22 C30 117.0(7) . . ?
C24 C23 C22 119.9(8) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C25 C24 C23 122.8(8) . . ?
C25 C24 H24 118.6 . . ?
C23 C24 H24 118.6 . . ?
C24 C25 C26 120.5(7) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C30 C26 C27 119.5(7) . . ?
C30 C26 C25 115.5(7) . . ?
C27 C26 C25 125.0(7) . . ?
C28 C27 N10 120.2(8) . . ?
C28 C27 C26 117.4(7) . . ?
N10 C27 C26 122.4(7) . . ?
C29 C28 C27 119.7(8) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
N9 C29 C28 126.3(7) . . ?
N9 C29 H29 116.9 . . ?
C28 C29 H29 116.9 . . ?
N9 C30 C22 114.9(6) . . ?
N9 C30 C26 120.7(7) . . ?
C22 C30 C26 124.3(7) . . ?
N10 C31 H31A 109.5 . . ?
N10 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N10 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N10 C32 H32A 109.5 . . ?
N10 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N10 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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
C6 N1 C1 N3 -41.6(11) . . . . ?
Cu1 N1 C1 N3 125.2(6) . . . . ?
C6 N1 C1 N2 138.3(7) . . . . ?
Cu1 N1 C1 N2 -54.9(9) . . . . ?
N1 C1 N2 C3 -21.6(10) . . . . ?
N3 C1 N2 C3 158.4(6) . . . . ?
N1 C1 N2 C5 149.8(7) . . . . ?
N3 C1 N2 C5 -30.2(9) . . . . ?
N1 C1 N3 C4 147.9(7) . . . . ?
N2 C1 N3 C4 -32.0(10) . . . . ?
N1 C1 N3 C2 -30.0(10) . . . . ?
N2 C1 N3 C2 150.0(7) . . . . ?
C1 N1 C6 C7 -7.1(12) . . . . ?
Cu1 N1 C6 C7 -175.4(7) . . . . ?
C1 N1 C6 C14 173.4(7) . . . . ?
Cu1 N1 C6 C14 5.2(8) . . . . ?
N1 C6 C7 C8 178.8(7) . . . . ?
C14 C6 C7 C8 -1.8(12) . . . . ?
C6 C7 C8 C9 1.4(13) . . . . ?
C7 C8 C9 C10 2.3(12) . . . . ?
C8 C9 C10 C14 -5.3(11) . . . . ?
C8 C9 C10 C11 -179.4(7) . . . . ?
C15 N5 C11 C10 -46.1(11) . . . . ?
C16 N5 C11 C10 162.8(7) . . . . ?
C15 N5 C11 C12 138.0(8) . . . . ?
C16 N5 C11 C12 -13.1(11) . . . . ?
C9 C10 C11 N5 -6.7(12) . . . . ?
C14 C10 C11 N5 179.4(7) . . . . ?
C9 C10 C11 C12 169.4(7) . . . . ?
C14 C10 C11 C12 -4.6(10) . . . . ?
N5 C11 C12 C13 -179.9(7) . . . . ?
C10 C11 C12 C13 3.8(10) . . . . ?
C14 N4 C13 C12 -5.9(11) . . . . ?
Cu1 N4 C13 C12 -178.3(6) . . . . ?
C11 C12 C13 N4 1.5(12) . . . . ?
C13 N4 C14 C10 4.9(11) . . . . ?
Cu1 N4 C14 C10 178.2(6) . . . . ?
C13 N4 C14 C6 -174.1(7) . . . . ?
Cu1 N4 C14 C6 -0.8(8) . . . . ?
C9 C10 C14 N4 -174.0(7) . . . . ?
C11 C10 C14 N4 0.3(11) . . . . ?
C9 C10 C14 C6 5.0(11) . . . . ?
C11 C10 C14 C6 179.3(7) . . . . ?
C7 C6 C14 N4 177.6(7) . . . . ?
N1 C6 C14 N4 -2.9(10) . . . . ?
C7 C6 C14 C10 -1.5(11) . . . . ?
N1 C6 C14 C10 178.0(7) . . . . ?
C20 N7 C17 N6 145.5(7) . . . . ?
C18 N7 C17 N6 -25.3(10) . . . . ?
C20 N7 C17 N8 -30.0(10) . . . . ?
C18 N7 C17 N8 159.2(6) . . . . ?
C22 N6 C17 N7 142.0(7) . . . . ?
Cu1 N6 C17 N7 -54.9(9) . . . . ?
C22 N6 C17 N8 -42.7(10) . . . . ?
Cu1 N6 C17 N8 120.4(6) . . . . ?
C21 N8 C17 N7 -34.4(10) . . . . ?
C19 N8 C17 N7 149.9(6) . . . . ?
C21 N8 C17 N6 150.3(7) . . . . ?
C19 N8 C17 N6 -25.4(10) . . . . ?
C17 N6 C22 C23 -14.4(11) . . . . ?
Cu1 N6 C22 C23 -179.4(6) . . . . ?
C17 N6 C22 C30 171.9(6) . . . . ?
Cu1 N6 C22 C30 6.9(7) . . . . ?
N6 C22 C23 C24 -174.8(7) . . . . ?
C30 C22 C23 C24 -1.1(10) . . . . ?
C22 C23 C24 C25 -0.1(12) . . . . ?
C23 C24 C25 C26 -0.4(12) . . . . ?
C24 C25 C26 C30 2.0(10) . . . . ?
C24 C25 C26 C27 179.8(7) . . . . ?
C32 N10 C27 C28 10.9(10) . . . . ?
C31 N10 C27 C28 -137.6(7) . . . . ?
C32 N10 C27 C26 -166.8(7) . . . . ?
C31 N10 C27 C26 44.6(10) . . . . ?
C30 C26 C27 C28 7.1(10) . . . . ?
C25 C26 C27 C28 -170.7(7) . . . . ?
C30 C26 C27 N10 -175.2(6) . . . . ?
C25 C26 C27 N10 7.1(11) . . . . ?
N10 C27 C28 C29 176.4(7) . . . . ?
C26 C27 C28 C29 -5.8(10) . . . . ?
C30 N9 C29 C28 0.8(10) . . . . ?
Cu1 N9 C29 C28 -172.6(5) . . . . ?
C27 C28 C29 N9 2.0(11) . . . . ?
C29 N9 C30 C22 177.7(6) . . . . ?
Cu1 N9 C30 C22 -7.8(7) . . . . ?
C29 N9 C30 C26 0.6(9) . . . . ?
Cu1 N9 C30 C26 175.1(5) . . . . ?
N6 C22 C30 N9 0.4(9) . . . . ?
C23 C22 C30 N9 -174.0(6) . . . . ?
N6 C22 C30 C26 177.4(6) . . . . ?
C23 C22 C30 C26 3.0(10) . . . . ?
C27 C26 C30 N9 -4.5(10) . . . . ?
C25 C26 C30 N9 173.4(6) . . . . ?
C27 C26 C30 C22 178.6(6) . . . . ?
C25 C26 C30 C22 -3.4(10) . . . . ?

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 H4A Br2 0.98 2.88 3.799(8) 156.8 . yes
C7 H7 N3 0.95 2.46 2.954(10) 112.6 . yes
C12 H12 Br1 0.95 2.88 3.633(7) 137.0 2_776 yes
C23 H23 N8 0.95 2.54 3.016(10) 110.8 . yes
C28 H28 Br1 0.95 2.88 3.598(8) 133.2 2_676 yes

_refine_diff_density_max         1.093
_refine_diff_density_min         -1.035
_refine_diff_density_rms         0.130



####################################################################### 
# 
# 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_C1B
_database_code_depnum_ccdc_archive 'CCDC 2118639'
loop_
_audit_author_name
_audit_author_address
'Alexander Hoffmann'
;RWTH Aachen University
Germany
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H23 Br2 Cu N5'
_chemical_formula_sum            'C13 H23 Br2 Cu N5'
_chemical_formula_weight         472.72

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                   8.7711(18)
_cell_length_b                   19.273(4)
_cell_length_c                   10.732(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.29(3)
_cell_angle_gamma                90
_cell_volume                     1765.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    38312
_cell_measurement_theta_min      2.11
_cell_measurement_theta_max      32.99

_exptl_crystal_description       block
_exptl_crystal_colour            'green brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_F_000             940
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    5.764
_shelx_estimated_absorpt_T_min   0.478
_shelx_estimated_absorpt_T_max   0.545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1427
_exptl_absorpt_correction_T_max  0.5016
_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      
; 2941 frames, detector distance = 70 mm
;

_diffrn_reflns_number            21006
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.218
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3465
_reflns_number_gt                3180
_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)+(0.0283P)²+19.0348P] 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         3465
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1221
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_restrained_S_all      1.196
_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
Br1 Br 0.47020(9) 0.13623(4) 0.18769(6) 0.03101(19) Uani 1 1 d . . . . .
Cu1 Cu 0.43277(8) 0.18905(4) 0.37640(7) 0.01568(18) Uani 1 1 d . . . . .
C1 C 0.5392(7) 0.1802(3) 0.6577(6) 0.0176(12) Uani 1 1 d . . . . .
N1 N 0.5119(6) 0.2188(2) 0.5537(4) 0.0166(10) Uani 1 1 d . . . . .
N4 N 0.4967(6) 0.2838(2) 0.3381(4) 0.0160(10) Uani 1 1 d . . . . .
C4 C 0.6220(8) 0.1824(3) 0.8950(6) 0.0245(13) Uani 1 1 d . . . . .
H4A H 0.710990 0.155899 0.879150 0.037 Uiso 1 1 calc R U . . .
H4B H 0.562419 0.153484 0.942082 0.037 Uiso 1 1 calc R U . . .
H4C H 0.660529 0.223756 0.945664 0.037 Uiso 1 1 calc R U . . .
N3 N 0.5200(6) 0.2035(3) 0.7722(5) 0.0185(10) Uani 1 1 d . . . . .
C3 C 0.5443(8) 0.0576(3) 0.7249(7) 0.0292(15) Uani 1 1 d . . . . .
H3A H 0.493528 0.021465 0.665298 0.044 Uiso 1 1 calc R U . . .
H3B H 0.470494 0.074862 0.773685 0.044 Uiso 1 1 calc R U . . .
H3C H 0.636466 0.038053 0.783925 0.044 Uiso 1 1 calc R U . . .
Br2 Br 0.23299(7) 0.11350(3) 0.41159(6) 0.02597(18) Uani 1 1 d . . . . .
C2 C 0.6650(7) 0.0925(3) 0.5518(6) 0.0209(12) Uani 1 1 d . . . . .
H2A H 0.584662 0.074217 0.480300 0.031 Uiso 1 1 calc R U . . .
H2B H 0.742292 0.056138 0.583820 0.031 Uiso 1 1 calc R U . . .
H2C H 0.717253 0.132131 0.522420 0.031 Uiso 1 1 calc R U . . .
N2 N 0.5925(6) 0.1144(3) 0.6533(5) 0.0197(10) Uani 1 1 d . . . . .
N5 N 0.6765(6) 0.4820(3) 0.3075(5) 0.0233(11) Uani 1 1 d . . . . .
C5 C 0.3925(7) 0.2495(3) 0.7836(6) 0.0234(13) Uani 1 1 d . . . . .
H5A H 0.313746 0.250358 0.702355 0.035 Uiso 1 1 calc R U . . .
H5B H 0.433346 0.296460 0.804395 0.035 Uiso 1 1 calc R U . . .
H5C H 0.344318 0.232693 0.851759 0.035 Uiso 1 1 calc R U . . .
C9 C 0.6150(7) 0.4183(3) 0.3166(6) 0.0190(12) Uani 1 1 d . . . . .
C8 C 0.6085(7) 0.3891(3) 0.4363(6) 0.0185(12) Uani 1 1 d . . . . .
H8 H 0.645558 0.414957 0.512625 0.022 Uiso 1 1 calc R U . . .
C7 C 0.5495(7) 0.3242(3) 0.4430(5) 0.0166(11) Uani 1 1 d . . . . .
C6 C 0.5302(7) 0.2942(3) 0.5681(5) 0.0191(12) Uani 1 1 d . . . . .
H6A H 0.623205 0.305134 0.637064 0.023 Uiso 1 1 calc R U . . .
H6AB H 0.436801 0.314489 0.591417 0.023 Uiso 1 1 calc R U . . .
C10 C 0.5577(7) 0.3765(3) 0.2075(6) 0.0185(12) Uani 1 1 d . . . . .
H10 H 0.556660 0.393421 0.124154 0.022 Uiso 1 1 calc R U . . .
C11 C 0.5040(7) 0.3117(3) 0.2241(6) 0.0195(12) Uani 1 1 d . . . . .
H11 H 0.468960 0.283977 0.149846 0.023 Uiso 1 1 calc R U . . .
C12 C 0.6578(8) 0.5157(3) 0.1818(7) 0.0267(14) Uani 1 1 d . . . . .
H12A H 0.693099 0.484043 0.122669 0.040 Uiso 1 1 calc R U . . .
H12B H 0.720686 0.558211 0.191202 0.040 Uiso 1 1 calc R U . . .
H12C H 0.547270 0.527237 0.147850 0.040 Uiso 1 1 calc R U . . .
C13 C 0.7312(9) 0.5236(3) 0.4214(7) 0.0327(17) Uani 1 1 d . . . . .
H13A H 0.778261 0.566502 0.398589 0.049 Uiso 1 1 calc R U . . .
H13B H 0.809676 0.497465 0.483489 0.049 Uiso 1 1 calc R U . . .
H13C H 0.642690 0.535004 0.459194 0.049 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 2.3562(10) . ?
Cu1 N1 1.955(5) . ?
Cu1 N4 1.981(5) . ?
Cu1 Br2 2.3744(10) . ?
C1 N1 1.316(8) . ?
C1 N3 1.354(8) . ?
C1 N2 1.356(8) . ?
N1 C6 1.467(7) . ?
N4 C11 1.352(8) . ?
N4 C7 1.360(7) . ?
C4 N3 1.470(7) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N3 C5 1.454(8) . ?
C3 N2 1.456(8) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C2 N2 1.445(8) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N5 C9 1.353(8) . ?
N5 C13 1.449(8) . ?
N5 C12 1.472(8) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C9 C10 1.414(8) . ?
C9 C8 1.416(8) . ?
C8 C7 1.360(8) . ?
C8 H8 0.9500 . ?
C7 C6 1.508(8) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C10 C11 1.361(8) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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 N4 82.99(19) . . ?
N1 Cu1 Br1 151.01(15) . . ?
N4 Cu1 Br1 96.77(14) . . ?
N1 Cu1 Br2 97.73(14) . . ?
N4 Cu1 Br2 148.52(14) . . ?
Br1 Cu1 Br2 97.21(4) . . ?
N1 C1 N3 123.1(5) . . ?
N1 C1 N2 119.7(5) . . ?
N3 C1 N2 117.2(5) . . ?
C1 N1 C6 118.4(5) . . ?
C1 N1 Cu1 127.9(4) . . ?
C6 N1 Cu1 113.5(4) . . ?
C11 N4 C7 116.3(5) . . ?
C11 N4 Cu1 129.0(4) . . ?
C7 N4 Cu1 114.6(4) . . ?
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 . . ?
C1 N3 C5 122.5(5) . . ?
C1 N3 C4 123.0(5) . . ?
C5 N3 C4 114.5(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 . . ?
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 N2 C2 121.0(5) . . ?
C1 N2 C3 122.8(5) . . ?
C2 N2 C3 114.1(5) . . ?
C9 N5 C13 120.1(5) . . ?
C9 N5 C12 120.3(5) . . ?
C13 N5 C12 118.3(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 C9 C10 121.9(6) . . ?
N5 C9 C8 121.7(6) . . ?
C10 C9 C8 116.4(5) . . ?
C7 C8 C9 120.5(5) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
N4 C7 C8 123.0(5) . . ?
N4 C7 C6 115.5(5) . . ?
C8 C7 C6 121.4(5) . . ?
N1 C6 C7 108.6(5) . . ?
N1 C6 H6A 110.0 . . ?
C7 C6 H6A 110.0 . . ?
N1 C6 H6AB 110.0 . . ?
C7 C6 H6AB 110.0 . . ?
H6A C6 H6AB 108.4 . . ?
C11 C10 C9 118.8(5) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N4 C11 C10 125.0(6) . . ?
N4 C11 H11 117.5 . . ?
C10 C11 H11 117.5 . . ?
N5 C12 H12A 109.5 . . ?
N5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N5 C13 H13A 109.5 . . ?
N5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
N3 C1 N1 C6 28.0(8) . . . . ?
N2 C1 N1 C6 -150.4(5) . . . . ?
N3 C1 N1 Cu1 -147.0(5) . . . . ?
N2 C1 N1 Cu1 34.6(8) . . . . ?
N1 C1 N3 C5 37.8(8) . . . . ?
N2 C1 N3 C5 -143.8(6) . . . . ?
N1 C1 N3 C4 -144.8(6) . . . . ?
N2 C1 N3 C4 33.6(8) . . . . ?
N1 C1 N2 C2 19.2(8) . . . . ?
N3 C1 N2 C2 -159.3(5) . . . . ?
N1 C1 N2 C3 -143.4(6) . . . . ?
N3 C1 N2 C3 38.2(8) . . . . ?
C13 N5 C9 C10 178.8(6) . . . . ?
C12 N5 C9 C10 12.1(9) . . . . ?
C13 N5 C9 C8 -2.9(9) . . . . ?
C12 N5 C9 C8 -169.6(5) . . . . ?
N5 C9 C8 C7 -178.4(5) . . . . ?
C10 C9 C8 C7 0.0(8) . . . . ?
C11 N4 C7 C8 -0.7(8) . . . . ?
Cu1 N4 C7 C8 175.4(4) . . . . ?
C11 N4 C7 C6 176.0(5) . . . . ?
Cu1 N4 C7 C6 -7.9(6) . . . . ?
C9 C8 C7 N4 1.1(9) . . . . ?
C9 C8 C7 C6 -175.4(5) . . . . ?
C1 N1 C6 C7 160.3(5) . . . . ?
Cu1 N1 C6 C7 -24.0(6) . . . . ?
N4 C7 C6 N1 20.6(7) . . . . ?
C8 C7 C6 N1 -162.7(5) . . . . ?
N5 C9 C10 C11 177.0(6) . . . . ?
C8 C9 C10 C11 -1.4(8) . . . . ?
C7 N4 C11 C10 -0.8(9) . . . . ?
Cu1 N4 C11 C10 -176.2(5) . . . . ?
C9 C10 C11 N4 1.9(9) . . . . ?

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
C11 H11 Br1 0.95 2.88 3.410(6) 116.7 . yes
C12 H12C Br2 0.98 2.91 3.838(7) 157.5 2 yes
C13 H13A Br1 0.98 2.91 3.788(7) 149.6 2_655 yes

_refine_diff_density_max         2.028
_refine_diff_density_min         -1.174
_refine_diff_density_rms         0.151


