# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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data_2
_database_code_depnum_ccdc_archive 'CCDC 1861697'
_audit_update_record             
;
2018-10-25 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;
_audit_creation_date             2018-10-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C48 H36 Cu3 I3 N12 O6'
_chemical_formula_sum            'C48 H36 Cu3 I3 N12 O6'
_chemical_formula_weight         1448.21
_chemical_melting_point          ?
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   14.770(3)
_cell_length_b                   11.093(2)
_cell_length_c                   15.890(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.00(3)
_cell_angle_gamma                90
_cell_volume                     2476.1(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6090
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9564
_cell_measurement_theta_min      1.8357
_shelx_estimated_absorpt_T_max   0.761
_shelx_estimated_absorpt_T_min   0.662
_exptl_absorpt_coefficient_mu    3.209
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.6842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.942
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1404
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27048
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.498
_diffrn_reflns_theta_min         2.277
_diffrn_ambient_temperature      293.1500
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4706
_reflns_number_total             5134
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.126
_refine_diff_density_min         -1.164
_refine_diff_density_rms         0.132
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         5134
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0681
_refine_ls_restrained_S_all      1.194
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0540P)²+10.2231P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1536
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 C19-C11 \\sim C19A-C11
 with sigma of 0.01
 O3-C19 \\sim O3A-C19A
 with sigma of 0.01
 N5-C19 \\sim N5A-C19A \\sim N5A-C21 \\sim N5-C21
 with sigma of 0.01
3. Rigid bond restraints
 O3, C19, N5A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C19A \\sim C19: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02
O3 \\sim O3A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
O3 \\sim C19 \\sim N5A: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
N5A \\sim N5: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O3) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(N5A) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(O3A) \\sim Ueq, Uanis(O3) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5. Others
 Sof(N5A)=Sof(H5A)=Sof(O3A)=Sof(C19A)=1-FVAR(1)
 Sof(O3)=Sof(C19)=Sof(N5)=Sof(H5B)=FVAR(1)
6.a Riding coordinates:
 N5A(H5A), N5(H5B)
6.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4), C23(H23), C1(H1), C2(H2A), C3(H3), C5(H5), C8(H8), C10(H10),
 C12(H12), C14(H14), C16(H16), C17(H17), C18(H18), C20(H20), C22(H22), C24(H24)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.000000 -0.14455(13) 0.250000 0.0444(3) Uani 1 2 d S T P . .
Cu2 Cu 0.08212(9) -0.41164(12) 0.24137(8) 0.0727(4) Uani 1 1 d . . . . .
I1 I 0.12152(3) -0.27030(4) 0.37638(3) 0.04372(17) Uani 1 1 d . . . . .
I2 I 0.000000 -0.61394(7) 0.250000 0.0595(2) Uani 1 2 d S T P . .
O1 O 0.2462(4) -0.0759(5) -0.0555(3) 0.0582(15) Uani 1 1 d . . . . .
O2 O 0.6393(3) -0.0726(4) 0.2257(3) 0.0391(11) Uani 1 1 d . . . . .
O3 O 0.5315(6) 0.3090(9) -0.0677(7) 0.062(3) Uani 0.626(12) 1 d D U . A 1
N1 N 0.1379(4) -0.3759(5) 0.1450(4) 0.0408(14) Uani 1 1 d . . . . .
N2 N 0.2760(4) -0.1342(5) 0.0868(4) 0.0365(13) Uani 1 1 d . . . . .
H2 H 0.304301 -0.112552 0.140456 0.044 Uiso 1 1 calc R . . . .
N3 N 0.9285(4) -0.0217(5) 0.3050(4) 0.0360(12) Uani 1 1 d . . . . .
N4 N 0.6927(4) 0.1214(5) 0.2371(4) 0.0349(12) Uani 1 1 d . . . . .
H4 H 0.675988 0.195619 0.226744 0.042 Uiso 1 1 calc R . . . .
N5A N 0.3940(14) 0.3166(12) -0.1205(9) 0.038(4) Uani 0.374(12) 1 d D U . A 2
H5A H 0.349508 0.258624 -0.161248 0.045 Uiso 0.374(12) 1 d R . . A 2
C23 C 0.3810(6) 0.4764(8) -0.3186(5) 0.0520(19) Uani 1 1 d . . . . .
H23 H 0.392020 0.457536 -0.371632 0.062 Uiso 1 1 calc R . . . .
C1 C 0.1162(6) -0.4419(8) 0.0720(5) 0.053(2) Uani 1 1 d . . . . .
H1 H 0.082357 -0.512972 0.070690 0.064 Uiso 1 1 calc R . . . .
C2 C 0.1404(6) -0.4117(8) -0.0013(6) 0.058(2) Uani 1 1 d . . . . .
H2A H 0.122823 -0.461473 -0.050805 0.069 Uiso 1 1 calc R . . . .
C3 C 0.1913(6) -0.3066(7) -0.0021(5) 0.051(2) Uani 1 1 d . . . . .
H3 H 0.207466 -0.283935 -0.051990 0.062 Uiso 1 1 calc R . . . .
C4 C 0.2172(5) -0.2366(6) 0.0741(4) 0.0339(14) Uani 1 1 d . . . . .
C5 C 0.1879(5) -0.2752(6) 0.1459(5) 0.0372(15) Uani 1 1 d . . . . .
H5 H 0.204098 -0.228112 0.196786 0.045 Uiso 1 1 calc R . . . .
C6 C 0.2920(5) -0.0668(6) 0.0218(4) 0.0387(15) Uani 1 1 d . . . . .
C7 C 0.3740(4) 0.0210(6) 0.0500(4) 0.0325(14) Uani 1 1 d . . . . .
C8 C 0.4570(4) -0.0033(6) 0.1195(4) 0.0329(14) Uani 1 1 d . . . . .
H8 H 0.459823 -0.070484 0.155271 0.040 Uiso 1 1 calc R . . . .
C9 C 0.5357(4) 0.0732(6) 0.1352(4) 0.0323(14) Uani 1 1 d . . . . .
C10 C 0.5314(5) 0.1725(7) 0.0809(5) 0.0411(16) Uani 1 1 d . . . . .
H10 H 0.584001 0.222820 0.090777 0.049 Uiso 1 1 calc R . . . .
C11 C 0.4484(5) 0.1975(6) 0.0113(5) 0.0392(16) Uani 1 1 d D . . . .
C12 C 0.3709(5) 0.1217(6) -0.0036(5) 0.0369(15) Uani 1 1 d . . . . .
H12 H 0.315866 0.138012 -0.049858 0.044 Uiso 1 1 calc R . . . .
C13 C 0.6269(5) 0.0351(6) 0.2036(4) 0.0328(14) Uani 1 1 d . . . . .
C14 C 0.8384(4) 0.0071(6) 0.2612(4) 0.0333(14) Uani 1 1 d . . . . .
H14 H 0.807895 -0.034939 0.209616 0.040 Uiso 1 1 calc R . . . .
C15 C 0.7877(4) 0.0961(6) 0.2884(4) 0.0317(13) Uani 1 1 d . . . . .
C16 C 0.8337(5) 0.1606(7) 0.3638(5) 0.0503(19) Uani 1 1 d . . . . .
H16 H 0.802409 0.221542 0.384047 0.060 Uiso 1 1 calc R . . . .
C17 C 0.9276(6) 0.1323(9) 0.4084(6) 0.061(2) Uani 1 1 d . . . . .
H17 H 0.960447 0.174786 0.459100 0.073 Uiso 1 1 calc R . . . .
C18 C 0.9720(5) 0.0415(8) 0.3777(5) 0.0513(19) Uani 1 1 d . . . . .
H18 H 1.034949 0.023253 0.408785 0.062 Uiso 1 1 calc R . . . .
C19 C 0.4561(7) 0.2870(11) -0.0587(8) 0.038(3) Uani 0.626(12) 1 d D U . A 1
C20 C 0.3880(5) 0.3889(7) -0.2550(6) 0.049(2) Uani 1 1 d . . . . .
H20 H 0.403892 0.310216 -0.265093 0.059 Uiso 1 1 calc R . . . .
C21 C 0.3718(5) 0.4177(6) -0.1776(5) 0.0437(17) Uani 1 1 d D . . . .
C22 C 0.3485(7) 0.5362(8) -0.1674(6) 0.063(2) Uani 1 1 d . . . . .
H22 H 0.337301 0.557344 -0.114854 0.076 Uiso 1 1 calc R . . . .
N6 N 0.3410(7) 0.6224(6) -0.2277(5) 0.068(2) Uani 1 1 d . . . . .
C24 C 0.3576(6) 0.5915(7) -0.3020(5) 0.052(2) Uani 1 1 d . . . . .
H24 H 0.353138 0.650333 -0.344813 0.063 Uiso 1 1 calc R . . . .
O3A O 0.4973(14) 0.4081(15) -0.0040(12) 0.085(6) Uani 0.374(12) 1 d D U . A 2
C19A C 0.4488(14) 0.3212(12) -0.0307(11) 0.037(4) Uani 0.374(12) 1 d D U . A 2
N5 N 0.3701(6) 0.3416(10) -0.1059(7) 0.037(3) Uani 0.626(12) 1 d D U . A 1
H5B H 0.307040 0.334031 -0.106800 0.045 Uiso 0.626(12) 1 d R . . A 1


_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 I1 2.6406(12) . ?
Cu1 I1 2.6406(12) 2 ?
Cu1 N3 2.075(6) 2_655 ?
Cu1 N3 2.075(6) 1_455 ?
Cu2 Cu2 2.524(2) 2 ?
Cu2 I1 2.5745(14) . ?
Cu2 I2 2.5746(15) . ?
Cu2 N1 1.990(6) . ?
O1 C6 1.209(8) . ?
O2 C13 1.244(8) . ?
O3 C19 1.192(11) . ?
N1 C1 1.325(10) . ?
N1 C5 1.336(9) . ?
N2 H2 0.8600 . ?
N2 C4 1.406(8) . ?
N2 C6 1.353(9) . ?
N3 C14 1.336(8) . ?
N3 C18 1.335(9) . ?
N4 H4 0.8600 . ?
N4 C13 1.350(8) . ?
N4 C15 1.417(8) . ?
N5A H5A 1.0016 . ?
N5A C21 1.416(9) . ?
N5A C19A 1.406(10) . ?
C23 H23 0.9300 . ?
C23 C20 1.382(11) . ?
C23 C24 1.369(11) . ?
C1 H1 0.9300 . ?
C1 C2 1.361(12) . ?
C2 H2A 0.9300 . ?
C2 C3 1.390(11) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(10) . ?
C4 C5 1.406(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.510(9) . ?
C7 C8 1.400(9) . ?
C7 C12 1.397(9) . ?
C8 H8 0.9300 . ?
C8 C9 1.398(9) . ?
C9 C10 1.389(9) . ?
C9 C13 1.507(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.401(9) . ?
C11 C12 1.381(9) . ?
C11 C19 1.521(11) . ?
C11 C19A 1.527(12) . ?
C12 H12 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.386(9) . ?
C15 C16 1.380(10) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(11) . ?
C17 H17 0.9300 . ?
C17 C18 1.372(11) . ?
C18 H18 0.9300 . ?
C19 N5 1.397(9) . ?
C20 H20 0.9300 . ?
C20 C21 1.363(11) . ?
C21 C22 1.380(11) . ?
C21 N5 1.424(8) . ?
C22 H22 0.9300 . ?
C22 N6 1.334(10) . ?
N6 C24 1.324(11) . ?
C24 H24 0.9300 . ?
O3A C19A 1.198(13) . ?
N5 H5B 0.9306 . ?

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
I1 Cu1 I1 116.23(6) . 2 ?
N3 Cu1 I1 109.97(15) 1_455 . ?
N3 Cu1 I1 110.63(15) 1_455 2 ?
N3 Cu1 I1 109.97(15) 2_655 2 ?
N3 Cu1 I1 110.63(15) 2_655 . ?
N3 Cu1 N3 97.9(3) 2_655 1_455 ?
Cu2 Cu2 I1 83.50(5) 2 . ?
Cu2 Cu2 I2 60.65(3) 2 . ?
I1 Cu2 I2 118.38(5) . . ?
N1 Cu2 Cu2 136.4(2) . 2 ?
N1 Cu2 I1 118.63(17) . . ?
N1 Cu2 I2 121.90(18) . . ?
Cu2 I1 Cu1 76.26(5) . . ?
Cu2 I2 Cu2 58.71(6) . 2 ?
C1 N1 Cu2 121.2(5) . . ?
C1 N1 C5 117.0(6) . . ?
C5 N1 Cu2 121.1(5) . . ?
C4 N2 H2 117.2 . . ?
C6 N2 H2 117.2 . . ?
C6 N2 C4 125.6(6) . . ?
C14 N3 Cu1 119.5(4) . 1_655 ?
C18 N3 Cu1 122.5(5) . 1_655 ?
C18 N3 C14 117.4(6) . . ?
C13 N4 H4 118.3 . . ?
C13 N4 C15 123.4(5) . . ?
C15 N4 H4 118.3 . . ?
C21 N5A H5A 96.8 . . ?
C19A N5A H5A 137.4 . . ?
C19A N5A C21 124.6(13) . . ?
C20 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C24 C23 C20 118.7(7) . . ?
N1 C1 H1 118.1 . . ?
N1 C1 C2 123.8(7) . . ?
C2 C1 H1 118.1 . . ?
C1 C2 H2A 120.0 . . ?
C1 C2 C3 120.0(7) . . ?
C3 C2 H2A 120.0 . . ?
C2 C3 H3 121.2 . . ?
C4 C3 C2 117.7(7) . . ?
C4 C3 H3 121.2 . . ?
N2 C4 C5 117.5(6) . . ?
C3 C4 N2 124.6(6) . . ?
C3 C4 C5 117.8(6) . . ?
N1 C5 C4 123.6(6) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
O1 C6 N2 123.7(7) . . ?
O1 C6 C7 120.0(6) . . ?
N2 C6 C7 116.3(6) . . ?
C8 C7 C6 122.5(6) . . ?
C12 C7 C6 117.6(6) . . ?
C12 C7 C8 119.4(6) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.1(6) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C13 117.9(6) . . ?
C10 C9 C8 119.6(6) . . ?
C10 C9 C13 122.0(6) . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.6(6) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C19 117.5(7) . . ?
C10 C11 C19A 113.7(8) . . ?
C12 C11 C10 119.4(6) . . ?
C12 C11 C19 121.2(7) . . ?
C12 C11 C19A 126.0(9) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 120.9(6) . . ?
C11 C12 H12 119.5 . . ?
O2 C13 N4 123.1(6) . . ?
O2 C13 C9 119.6(6) . . ?
N4 C13 C9 117.3(6) . . ?
N3 C14 H14 118.1 . . ?
N3 C14 C15 123.7(6) . . ?
C15 C14 H14 118.1 . . ?
C14 C15 N4 119.8(6) . . ?
C16 C15 N4 122.0(6) . . ?
C16 C15 C14 118.2(6) . . ?
C15 C16 H16 120.9 . . ?
C15 C16 C17 118.2(7) . . ?
C17 C16 H16 120.9 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.9(7) . . ?
C18 C17 H17 120.1 . . ?
N3 C18 C17 122.6(7) . . ?
N3 C18 H18 118.7 . . ?
C17 C18 H18 118.7 . . ?
O3 C19 C11 120.3(8) . . ?
O3 C19 N5 125.1(9) . . ?
N5 C19 C11 114.5(8) . . ?
C23 C20 H20 120.0 . . ?
C21 C20 C23 120.0(7) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 N5A 108.8(10) . . ?
C20 C21 C22 116.7(7) . . ?
C20 C21 N5 129.4(8) . . ?
C22 C21 N5A 134.1(10) . . ?
C22 C21 N5 113.9(8) . . ?
C21 C22 H22 117.7 . . ?
N6 C22 C21 124.6(8) . . ?
N6 C22 H22 117.7 . . ?
C24 N6 C22 117.2(7) . . ?
C23 C24 H24 118.6 . . ?
N6 C24 C23 122.7(7) . . ?
N6 C24 H24 118.6 . . ?
N5A C19A C11 109.4(9) . . ?
O3A C19A N5A 118.9(14) . . ?
O3A C19A C11 130.6(13) . . ?
C19 N5 C21 116.7(8) . . ?
C19 N5 H5B 135.1 . . ?
C21 N5 H5B 107.8 . . ?

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
N2 H2 O2 0.86 2.08 2.933(7) 173.2 2_655 yes

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
Cu1 N3 C14 C15 -173.8(5) 1_655 . . . ?
Cu1 N3 C18 C17 172.4(7) 1_655 . . . ?
Cu2 N1 C1 C2 169.8(7) . . . . ?
Cu2 N1 C5 C4 -170.5(5) . . . . ?
O1 C6 C7 C8 -144.6(7) . . . . ?
O1 C6 C7 C12 26.6(10) . . . . ?
O3 C19 N5 C21 8(2) . . . . ?
N1 C1 C2 C3 0.3(15) . . . . ?
N2 C4 C5 N1 -174.9(6) . . . . ?
N2 C6 C7 C8 33.7(9) . . . . ?
N2 C6 C7 C12 -155.2(6) . . . . ?
N3 C14 C15 N4 179.2(6) . . . . ?
N3 C14 C15 C16 1.7(10) . . . . ?
N4 C15 C16 C17 -178.0(7) . . . . ?
N5A C21 C22 N6 171.4(14) . . . . ?
C23 C20 C21 N5A -173.4(11) . . . . ?
C23 C20 C21 C22 0.1(12) . . . . ?
C23 C20 C21 N5 176.3(8) . . . . ?
C1 N1 C5 C4 0.4(11) . . . . ?
C1 C2 C3 C4 1.1(14) . . . . ?
C2 C3 C4 N2 173.9(7) . . . . ?
C2 C3 C4 C5 -1.7(12) . . . . ?
C3 C4 C5 N1 1.0(11) . . . . ?
C4 N2 C6 O1 11.6(11) . . . . ?
C4 N2 C6 C7 -166.6(6) . . . . ?
C5 N1 C1 C2 -1.1(12) . . . . ?
C6 N2 C4 C3 21.8(11) . . . . ?
C6 N2 C4 C5 -162.7(7) . . . . ?
C6 C7 C8 C9 171.3(6) . . . . ?
C6 C7 C12 C11 -171.5(7) . . . . ?
C7 C8 C9 C10 -0.8(10) . . . . ?
C7 C8 C9 C13 -172.9(6) . . . . ?
C8 C7 C12 C11 -0.1(10) . . . . ?
C8 C9 C10 C11 0.9(11) . . . . ?
C8 C9 C13 O2 19.9(9) . . . . ?
C8 C9 C13 N4 -161.1(6) . . . . ?
C9 C10 C11 C12 -0.6(11) . . . . ?
C9 C10 C11 C19 -165.1(9) . . . . ?
C9 C10 C11 C19A 169.2(11) . . . . ?
C10 C9 C13 O2 -152.0(7) . . . . ?
C10 C9 C13 N4 27.0(10) . . . . ?
C10 C11 C12 C7 0.2(11) . . . . ?
C10 C11 C19 O3 20.0(18) . . . . ?
C10 C11 C19 N5 -157.5(11) . . . . ?
C10 C11 C19A N5A 150.1(16) . . . . ?
C10 C11 C19A O3A -17(3) . . . . ?
C11 C19 N5 C21 -174.4(9) . . . . ?
C12 C7 C8 C9 0.4(10) . . . . ?
C12 C11 C19 O3 -144.3(13) . . . . ?
C12 C11 C19 N5 38.3(17) . . . . ?
C12 C11 C19A N5A -41(2) . . . . ?
C12 C11 C19A O3A 152(2) . . . . ?
C13 N4 C15 C14 45.4(9) . . . . ?
C13 N4 C15 C16 -137.2(7) . . . . ?
C13 C9 C10 C11 172.6(7) . . . . ?
C14 N3 C18 C17 0.5(12) . . . . ?
C14 C15 C16 C17 -0.5(11) . . . . ?
C15 N4 C13 O2 11.4(10) . . . . ?
C15 N4 C13 C9 -167.5(6) . . . . ?
C15 C16 C17 C18 -0.5(14) . . . . ?
C16 C17 C18 N3 0.5(14) . . . . ?
C18 N3 C14 C15 -1.7(10) . . . . ?
C19 C11 C12 C7 164.2(8) . . . . ?
C20 C23 C24 N6 -0.3(14) . . . . ?
C20 C21 C22 N6 0.1(14) . . . . ?
C20 C21 N5 C19 65.5(16) . . . . ?
C21 N5A C19A C11 173.9(14) . . . . ?
C21 N5A C19A O3A -17(4) . . . . ?
C21 C22 N6 C24 -0.4(15) . . . . ?
C22 C21 N5 C19 -118.2(13) . . . . ?
C22 N6 C24 C23 0.4(14) . . . . ?
C24 C23 C20 C21 0.0(12) . . . . ?
C19A N5A C21 C20 133(2) . . . . ?
C19A N5A C21 C22 -38(3) . . . . ?
C19A C11 C12 C7 -168.3(12) . . . . ?
N5 C21 C22 N6 -176.7(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1861698'
_audit_update_record             
;
2018-10-25 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;
_audit_creation_date             2018-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H18 Br Cu N6 O3'
_chemical_formula_sum            'C24 H18 Br Cu N6 O3'
_chemical_formula_weight         581.89
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   31.938(6)
_cell_length_b                   7.7414(15)
_cell_length_c                   20.506(4)
_cell_angle_alpha                90
_cell_angle_beta                 120.00(3)
_cell_angle_gamma                90
_cell_volume                     4390.6(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5140
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9083
_cell_measurement_theta_min      2.2936
_shelx_estimated_absorpt_T_max   0.642
_shelx_estimated_absorpt_T_min   0.572
_exptl_absorpt_coefficient_mu    2.857
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15413
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.489
_diffrn_reflns_theta_min         2.013
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3381
_reflns_number_total             4076
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         4076
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0500
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0658P)²+6.6128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1303
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N2-H2
 0.87 with sigma of 0.02
3. Rigid bond restraints
 N6, C24
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
N6 \\sim C24: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N6) \\sim Ueq, Uanis(C24) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4A), C5(H5A), C8(H8), C10(H10), C12(H12), C14(H14),
 C16(H16), C17(H17), C18(H18), C20(H20), C22(H22), C24(H24)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.09304(2) 1.44034(7) 0.28894(3) 0.04270(19) Uani 1 1 d . . . . .
Br1 Br 0.07288(2) 1.72696(6) 0.23649(3) 0.05128(19) Uani 1 1 d . . . . .
O1 O 0.15365(14) 0.9758(4) 0.05924(18) 0.0502(9) Uani 1 1 d . . . . .
O2 O 0.02387(13) 0.2020(4) 0.0124(2) 0.0571(10) Uani 1 1 d . . . . .
O3 O 0.16663(12) 0.4963(4) -0.07966(17) 0.0428(8) Uani 1 1 d . . . . .
N1 N 0.13312(13) 1.3305(4) 0.24824(19) 0.0343(8) Uani 1 1 d . . . . .
N2 N 0.13379(13) 0.9387(4) 0.14960(19) 0.0335(8) Uani 1 1 d D . . . .
H2 H 0.1192(14) 0.872(5) 0.164(2) 0.034(12) Uiso 1 1 d D . . . .
N3 N -0.05793(12) 0.3076(4) 0.17127(18) 0.0323(8) Uani 1 1 d . . . . .
N4 N 0.02396(13) 0.3860(5) 0.0977(2) 0.0320(8) Uani 1 1 d . . . . .
H4 H 0.0364(18) 0.465(6) 0.126(3) 0.050(15) Uiso 1 1 d . . . . .
N5 N 0.16594(14) 0.2241(4) -0.0390(2) 0.0347(9) Uani 1 1 d . . . . .
H5 H 0.1599(13) 0.171(5) -0.013(2) 0.019(10) Uiso 1 1 d . . . . .
N6 N 0.23623(15) 0.1239(5) -0.1330(2) 0.0494(10) Uani 1 1 d . U . . .
C1 C 0.12323(15) 1.1746(5) 0.2154(2) 0.0320(9) Uani 1 1 d . . . . .
H1 H 0.098494 1.110246 0.214980 0.038 Uiso 1 1 calc R . . . .
C2 C 0.14784(15) 1.1044(5) 0.1822(2) 0.0293(9) Uani 1 1 d . . . . .
C3 C 0.18526(16) 1.1984(5) 0.1845(2) 0.0364(10) Uani 1 1 d . . . . .
H3 H 0.202934 1.154914 0.163355 0.044 Uiso 1 1 calc R . . . .
C4 C 0.19585(16) 1.3578(6) 0.2187(2) 0.0403(10) Uani 1 1 d . . . . .
H4A H 0.221062 1.423158 0.221216 0.048 Uiso 1 1 calc R . . . .
C5 C 0.16910(16) 1.4201(6) 0.2490(2) 0.0395(10) Uani 1 1 d . . . . .
H5A H 0.176302 1.529108 0.270993 0.047 Uiso 1 1 calc R . . . .
C6 C 0.13685(16) 0.8845(5) 0.0889(2) 0.0334(9) Uani 1 1 d . . . . .
C7 C 0.12170(15) 0.7024(5) 0.0627(2) 0.0290(9) Uani 1 1 d . . . . .
C8 C 0.08816(14) 0.6094(5) 0.0725(2) 0.0301(9) Uani 1 1 d . . . . .
H8 H 0.073568 0.659230 0.097387 0.036 Uiso 1 1 calc R . . . .
C9 C 0.07628(14) 0.4410(5) 0.0450(2) 0.0288(9) Uani 1 1 d . . . . .
C10 C 0.09850(14) 0.3675(5) 0.0083(2) 0.0300(9) Uani 1 1 d . . . . .
H10 H 0.090764 0.254954 -0.009689 0.036 Uiso 1 1 calc R . . . .
C11 C 0.13213(14) 0.4594(5) -0.0021(2) 0.0288(9) Uani 1 1 d . . . . .
C12 C 0.14249(14) 0.6284(5) 0.0243(2) 0.0298(9) Uani 1 1 d . . . . .
H12 H 0.163898 0.693139 0.015969 0.036 Uiso 1 1 calc R . . . .
C13 C 0.03900(15) 0.3320(5) 0.0499(2) 0.0334(9) Uani 1 1 d . . . . .
C14 C -0.02892(14) 0.3827(5) 0.1491(2) 0.0314(9) Uani 1 1 d . . . . .
H14 H -0.023917 0.501284 0.155483 0.038 Uiso 1 1 calc R . . . .
C15 C -0.00628(14) 0.2919(5) 0.1172(2) 0.0286(9) Uani 1 1 d . . . . .
C16 C -0.01242(16) 0.1132(5) 0.1092(2) 0.0377(10) Uani 1 1 d . . . . .
H16 H 0.002122 0.048035 0.087821 0.045 Uiso 1 1 calc R . . . .
C17 C -0.04090(17) 0.0373(5) 0.1341(2) 0.0416(11) Uani 1 1 d . . . . .
H17 H -0.045028 -0.081963 0.130833 0.050 Uiso 1 1 calc R . . . .
C18 C -0.06313(16) 0.1346(6) 0.1634(2) 0.0402(10) Uani 1 1 d . . . . .
H18 H -0.082668 0.079344 0.178664 0.048 Uiso 1 1 calc R . . . .
C19 C 0.15608(15) 0.3959(5) -0.0443(2) 0.0322(9) Uani 1 1 d . . . . .
C20 C 0.19208(18) -0.0425(6) -0.0648(3) 0.0447(11) Uani 1 1 d . . . . .
H20 H 0.177145 -0.099755 -0.042026 0.054 Uiso 1 1 calc R . . . .
C21 C 0.19013(14) 0.1347(5) -0.0701(2) 0.0310(9) Uani 1 1 d . . . . .
C22 C 0.21330(18) 0.2134(6) -0.1044(3) 0.0434(11) Uani 1 1 d . . . . .
H22 H 0.212825 0.333324 -0.107602 0.052 Uiso 1 1 calc R . . . .
C23 C 0.21609(18) -0.1349(6) -0.0932(3) 0.0453(12) Uani 1 1 d . . . . .
H23 H 0.219(2) -0.245(7) -0.088(3) 0.070(18) Uiso 1 1 d . . . . .
C24 C 0.23751(16) -0.0468(6) -0.1268(2) 0.0421(11) Uani 1 1 d . U . . .
H24 H 0.253683 -0.109545 -0.146147 0.050 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 Br1 2.4087(9) . ?
Cu1 N1 2.031(3) . ?
Cu1 N3 1.973(3) 2_565 ?
O1 C6 1.219(5) . ?
O2 C13 1.210(5) . ?
O3 C19 1.220(5) . ?
N1 C1 1.340(5) . ?
N1 C5 1.336(5) . ?
N2 H2 0.835(19) . ?
N2 C2 1.413(5) . ?
N2 C6 1.362(5) . ?
N3 C14 1.351(5) . ?
N3 C18 1.350(5) . ?
N4 H4 0.80(5) . ?
N4 C13 1.356(5) . ?
N4 C15 1.418(5) . ?
N5 H5 0.78(4) . ?
N5 C19 1.359(5) . ?
N5 C21 1.405(5) . ?
N6 C22 1.338(6) . ?
N6 C24 1.326(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.383(5) . ?
C2 C3 1.380(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(6) . ?
C4 H4A 0.9300 . ?
C4 C5 1.371(6) . ?
C5 H5A 0.9300 . ?
C6 C7 1.500(5) . ?
C7 C8 1.386(5) . ?
C7 C12 1.382(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.395(5) . ?
C9 C10 1.389(5) . ?
C9 C13 1.503(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.391(5) . ?
C11 C12 1.391(5) . ?
C11 C19 1.496(5) . ?
C12 H12 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.384(5) . ?
C15 C16 1.395(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.364(6) . ?
C18 H18 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.375(6) . ?
C20 C23 1.373(6) . ?
C21 C22 1.391(6) . ?
C22 H22 0.9300 . ?
C23 H23 0.86(5) . ?
C23 C24 1.371(7) . ?
C24 H24 0.9300 . ?

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 Br1 106.56(10) . . ?
N3 Cu1 Br1 125.73(10) 2_565 . ?
N3 Cu1 N1 123.84(14) 2_565 . ?
C1 N1 Cu1 123.0(3) . . ?
C5 N1 Cu1 119.5(3) . . ?
C5 N1 C1 117.3(3) . . ?
C2 N2 H2 120(3) . . ?
C6 N2 H2 115(3) . . ?
C6 N2 C2 124.2(3) . . ?
C14 N3 Cu1 122.9(3) . 2_545 ?
C18 N3 Cu1 120.3(3) . 2_545 ?
C18 N3 C14 116.8(3) . . ?
C13 N4 H4 122(4) . . ?
C13 N4 C15 125.7(4) . . ?
C15 N4 H4 110(4) . . ?
C19 N5 H5 116(3) . . ?
C19 N5 C21 127.2(4) . . ?
C21 N5 H5 116(3) . . ?
C24 N6 C22 118.1(4) . . ?
N1 C1 H1 118.3 . . ?
N1 C1 C2 123.5(4) . . ?
C2 C1 H1 118.3 . . ?
C1 C2 N2 117.8(4) . . ?
C3 C2 N2 124.0(4) . . ?
C3 C2 C1 118.2(4) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 C2 118.6(4) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 C3 119.8(4) . . ?
C5 C4 H4A 120.1 . . ?
N1 C5 C4 122.7(4) . . ?
N1 C5 H5A 118.7 . . ?
C4 C5 H5A 118.7 . . ?
O1 C6 N2 121.9(4) . . ?
O1 C6 C7 120.6(4) . . ?
N2 C6 C7 117.4(3) . . ?
C8 C7 C6 124.7(3) . . ?
C12 C7 C6 115.7(3) . . ?
C12 C7 C8 119.6(4) . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.0(4) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C13 124.2(4) . . ?
C10 C9 C8 119.5(4) . . ?
C10 C9 C13 116.3(3) . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.1(4) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 118.2(3) . . ?
C10 C11 C19 125.3(4) . . ?
C12 C11 C19 116.3(3) . . ?
C7 C12 C11 121.5(4) . . ?
C7 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
O2 C13 N4 122.8(4) . . ?
O2 C13 C9 120.2(4) . . ?
N4 C13 C9 117.0(4) . . ?
N3 C14 H14 118.4 . . ?
N3 C14 C15 123.3(4) . . ?
C15 C14 H14 118.4 . . ?
C14 C15 N4 117.6(4) . . ?
C14 C15 C16 118.9(4) . . ?
C16 C15 N4 123.4(4) . . ?
C15 C16 H16 121.4 . . ?
C17 C16 C15 117.3(4) . . ?
C17 C16 H16 121.4 . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 120.9(4) . . ?
C18 C17 H17 119.5 . . ?
N3 C18 C17 122.7(4) . . ?
N3 C18 H18 118.6 . . ?
C17 C18 H18 118.6 . . ?
O3 C19 N5 123.3(4) . . ?
O3 C19 C11 120.5(4) . . ?
N5 C19 C11 116.2(4) . . ?
C21 C20 H20 120.0 . . ?
C23 C20 H20 120.0 . . ?
C23 C20 C21 120.0(4) . . ?
C20 C21 N5 118.0(4) . . ?
C20 C21 C22 117.5(4) . . ?
C22 C21 N5 124.4(4) . . ?
N6 C22 C21 122.8(4) . . ?
N6 C22 H22 118.6 . . ?
C21 C22 H22 118.6 . . ?
C20 C23 H23 121(4) . . ?
C24 C23 C20 118.6(4) . . ?
C24 C23 H23 121(4) . . ?
N6 C24 C23 123.0(4) . . ?
N6 C24 H24 118.5 . . ?
C23 C24 H24 118.5 . . ?

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
N4 H4 Br1 0.80(5) 2.82(5) 3.614(4) 172(5) 1_545 yes

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
Cu1 N1 C1 C2 174.7(3) . . . . ?
Cu1 N1 C5 C4 -176.3(3) . . . . ?
Cu1 N3 C14 C15 -176.3(3) 2_545 . . . ?
Cu1 N3 C18 C17 177.9(4) 2_545 . . . ?
O1 C6 C7 C8 -156.5(4) . . . . ?
O1 C6 C7 C12 21.5(6) . . . . ?
N1 C1 C2 N2 180.0(4) . . . . ?
N1 C1 C2 C3 1.5(6) . . . . ?
N2 C2 C3 C4 -179.3(4) . . . . ?
N2 C6 C7 C8 27.3(6) . . . . ?
N2 C6 C7 C12 -154.6(4) . . . . ?
N3 C14 C15 N4 -178.9(4) . . . . ?
N3 C14 C15 C16 -1.7(6) . . . . ?
N4 C15 C16 C17 176.7(4) . . . . ?
N5 C21 C22 N6 179.6(4) . . . . ?
C1 N1 C5 C4 -0.7(6) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C2 N2 C6 O1 2.2(7) . . . . ?
C2 N2 C6 C7 178.3(4) . . . . ?
C2 C3 C4 C5 -0.5(7) . . . . ?
C3 C4 C5 N1 1.3(7) . . . . ?
C5 N1 C1 C2 -0.7(6) . . . . ?
C6 N2 C2 C1 149.0(4) . . . . ?
C6 N2 C2 C3 -32.6(6) . . . . ?
C6 C7 C8 C9 179.3(4) . . . . ?
C6 C7 C12 C11 179.0(4) . . . . ?
C7 C8 C9 C10 0.4(6) . . . . ?
C7 C8 C9 C13 -177.4(4) . . . . ?
C8 C7 C12 C11 -2.8(6) . . . . ?
C8 C9 C10 C11 -0.5(6) . . . . ?
C8 C9 C13 O2 165.5(4) . . . . ?
C8 C9 C13 N4 -14.8(6) . . . . ?
C9 C10 C11 C12 -0.9(6) . . . . ?
C9 C10 C11 C19 -176.6(4) . . . . ?
C10 C9 C13 O2 -12.3(6) . . . . ?
C10 C9 C13 N4 167.3(4) . . . . ?
C10 C11 C12 C7 2.6(6) . . . . ?
C10 C11 C19 O3 146.7(4) . . . . ?
C10 C11 C19 N5 -34.7(6) . . . . ?
C12 C7 C8 C9 1.2(6) . . . . ?
C12 C11 C19 O3 -29.0(6) . . . . ?
C12 C11 C19 N5 149.6(4) . . . . ?
C13 N4 C15 C14 -162.2(4) . . . . ?
C13 N4 C15 C16 20.8(6) . . . . ?
C13 C9 C10 C11 177.4(4) . . . . ?
C14 N3 C18 C17 -0.5(6) . . . . ?
C14 C15 C16 C17 -0.3(6) . . . . ?
C15 N4 C13 O2 7.7(7) . . . . ?
C15 N4 C13 C9 -171.9(4) . . . . ?
C15 C16 C17 C18 1.8(7) . . . . ?
C16 C17 C18 N3 -1.4(7) . . . . ?
C18 N3 C14 C15 2.1(6) . . . . ?
C19 N5 C21 C20 -173.4(4) . . . . ?
C19 N5 C21 C22 8.1(7) . . . . ?
C19 C11 C12 C7 178.6(4) . . . . ?
C20 C21 C22 N6 1.2(7) . . . . ?
C20 C23 C24 N6 0.2(7) . . . . ?
C21 N5 C19 O3 1.8(7) . . . . ?
C21 N5 C19 C11 -176.7(4) . . . . ?
C21 C20 C23 C24 -0.3(7) . . . . ?
C22 N6 C24 C23 0.6(7) . . . . ?
C23 C20 C21 N5 -178.9(4) . . . . ?
C23 C20 C21 C22 -0.3(7) . . . . ?
C24 N6 C22 C21 -1.3(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
