# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 1981488'
loop_
_audit_author_name
_audit_author_address
'Jhy-Der Chen'
;Chung Yuan Christian University
Taiwan
;
_audit_update_record             
;
2020-04-09 deposited with the CCDC.	2020-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H25 Br2 Cu4 N9 O'
_chemical_formula_weight         881.52

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'
O O 0.0106 0.0060 '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                   12.08960(10)
_cell_length_b                   13.6597(2)
_cell_length_c                   17.8304(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.5350(10)
_cell_angle_gamma                90
_cell_volume                     2885.05(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9877
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.61

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.029
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    5.717
_shelx_estimated_absorpt_T_min   0.279
_shelx_estimated_absorpt_T_max   0.763
_exptl_absorpt_correction_type   multi_scan
_exptl_absorpt_correction_T_min  0.4042
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26474
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.719
_diffrn_reflns_theta_max         28.292
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7107
_reflns_number_gt                4253
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0440P)²+1.8004P] 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         7107
_refine_ls_number_parameters     367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1064
_refine_ls_wR_factor_gt          0.0906
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.73635(4) 0.51816(5) 0.69917(3) 0.04633(17) Uani 1 1 d . . . . .
Cu2 Cu 0.57181(4) 0.43691(5) 0.73552(3) 0.04819(17) Uani 1 1 d . . . . .
Cu3 Cu 0.40439(4) 0.36038(5) 0.77186(3) 0.04912(18) Uani 1 1 d . . . . .
Cu4 Cu 0.24859(4) 0.26425(5) 0.80714(3) 0.04755(17) Uani 1 1 d . . . . .
Br1 Br 0.88100(4) 0.63070(3) 0.65567(2) 0.04435(14) Uani 1 1 d . . . . .
Br2 Br 0.40898(4) 0.14411(3) 0.77126(2) 0.04054(13) Uani 1 1 d . . . . .
N1 N 0.6699(3) 0.4434(2) 0.59972(16) 0.0350(8) Uani 1 1 d . . . . .
N2 N 0.4987(3) 0.4087(3) 0.63250(16) 0.0344(8) Uani 1 1 d . . . . .
N3 N 0.3299(3) 0.3714(2) 0.66755(17) 0.0373(9) Uani 1 1 d . . . . .
N4 N 0.1681(3) 0.3076(3) 0.70034(17) 0.0384(8) Uani 1 1 d . . . . .
N5 N 0.8137(3) 0.4624(3) 0.80410(18) 0.0454(9) Uani 1 1 d . . . . .
N6 N 0.6476(3) 0.4117(3) 0.83841(16) 0.0356(8) Uani 1 1 d . . . . .
N7 N 0.4806(3) 0.3743(2) 0.87550(16) 0.0354(8) Uani 1 1 d . . . . .
N8 N 0.3152(3) 0.3244(3) 0.91070(17) 0.0370(8) Uani 1 1 d . . . . .
C1 C 0.7420(4) 0.4371(3) 0.5511(2) 0.0422(11) Uani 1 1 d . . . . .
H1A H 0.8145 0.4620 0.5668 0.051 Uiso 1 1 calc R U . . .
C2 C 0.7140(4) 0.3958(4) 0.4795(2) 0.0500(12) Uani 1 1 d . . . . .
H2A H 0.7671 0.3901 0.4485 0.060 Uiso 1 1 calc R U . . .
C3 C 0.6046(4) 0.3628(3) 0.4550(2) 0.0484(12) Uani 1 1 d . . . . .
H3A H 0.5821 0.3368 0.4061 0.058 Uiso 1 1 calc R U . . .
C4 C 0.5299(4) 0.3686(3) 0.5027(2) 0.0421(11) Uani 1 1 d . . . . .
H4A H 0.4561 0.3470 0.4864 0.050 Uiso 1 1 calc R U . . .
C5 C 0.5647(3) 0.4075(3) 0.57672(19) 0.0318(9) Uani 1 1 d . . . . .
C6 C 0.3914(3) 0.3851(3) 0.6143(2) 0.0346(10) Uani 1 1 d . . . . .
H6A H 0.3575 0.3779 0.5630 0.041 Uiso 1 1 calc R U . . .
C7 C 0.2155(3) 0.3499(3) 0.6466(2) 0.0368(10) Uani 1 1 d . . . . .
C8 C 0.1503(4) 0.3714(3) 0.5738(2) 0.0471(12) Uani 1 1 d . . . . .
H8A H 0.1826 0.4042 0.5379 0.057 Uiso 1 1 calc R U . . .
C9 C 0.0398(4) 0.3442(4) 0.5561(3) 0.0622(15) Uani 1 1 d . . . . .
H9A H -0.0026 0.3559 0.5074 0.075 Uiso 1 1 calc R U . . .
C10 C -0.0084(4) 0.2994(4) 0.6102(3) 0.0662(16) Uani 1 1 d . . . . .
H10A H -0.0838 0.2804 0.5992 0.079 Uiso 1 1 calc R U . . .
C11 C 0.0582(4) 0.2834(4) 0.6816(3) 0.0560(13) Uani 1 1 d . . . . .
H11A H 0.0252 0.2543 0.7189 0.067 Uiso 1 1 calc R U . . .
C12 C 0.9267(4) 0.4724(5) 0.8191(3) 0.0790(19) Uani 1 1 d . . . . .
H12A H 0.9606 0.5011 0.7821 0.095 Uiso 1 1 calc R U . . .
C13 C 0.9948(5) 0.4421(6) 0.8867(4) 0.106(3) Uani 1 1 d . . . . .
H13A H 1.0726 0.4512 0.8957 0.127 Uiso 1 1 calc R U . . .
C14 C 0.9448(5) 0.3988(5) 0.9396(3) 0.093(2) Uani 1 1 d . . . . .
H14A H 0.9887 0.3769 0.9855 0.111 Uiso 1 1 calc R U . . .
C15 C 0.8312(4) 0.3872(4) 0.9262(3) 0.0611(14) Uani 1 1 d . . . . .
H15A H 0.7973 0.3570 0.9626 0.073 Uiso 1 1 calc R U . . .
C16 C 0.7649(3) 0.4208(3) 0.8575(2) 0.0403(10) Uani 1 1 d . . . . .
C17 C 0.5908(4) 0.3906(3) 0.8923(2) 0.0358(10) Uani 1 1 d . . . . .
H17A H 0.6289 0.3872 0.9430 0.043 Uiso 1 1 calc R U . . .
C18 C 0.4199(4) 0.3608(3) 0.9331(2) 0.0343(10) Uani 1 1 d . . . . .
C19 C 0.4623(4) 0.3852(3) 1.0105(2) 0.0449(12) Uani 1 1 d . . . . .
H19A H 0.5360 0.4075 1.0256 0.054 Uiso 1 1 calc R U . . .
C20 C 0.3948(5) 0.3760(3) 1.0633(2) 0.0541(14) Uani 1 1 d . . . . .
H20A H 0.4221 0.3918 1.1144 0.065 Uiso 1 1 calc R U . . .
C21 C 0.2863(5) 0.3432(3) 1.0397(3) 0.0546(13) Uani 1 1 d . . . . .
H21A H 0.2378 0.3388 1.0741 0.066 Uiso 1 1 calc R U . . .
C22 C 0.2499(4) 0.3168(3) 0.9638(2) 0.0466(11) Uani 1 1 d . . . . .
H22A H 0.1770 0.2926 0.9486 0.056 Uiso 1 1 calc R U . . .
O O -0.2609(6) 0.1077(8) 0.5848(3) 0.221(5) Uani 1 1 d . . . . .
N9 N -0.2466(4) 0.1348(3) 0.7068(2) 0.0582(11) Uani 1 1 d . . . . .
C23 C -0.2328(8) 0.0667(7) 0.6571(10) 0.216(7) Uani 1 1 d . . . . .
H23A H -0.2086 0.0028 0.6685 0.260 Uiso 1 1 calc R U . . .
C24 C -0.2309(8) 0.1214(10) 0.7857(4) 0.233(8) Uani 1 1 d . . . . .
H24A H -0.1938 0.0600 0.7993 0.350 Uiso 1 1 calc R U . . .
H24B H -0.3029 0.1214 0.8006 0.350 Uiso 1 1 calc R U . . .
H24C H -0.1854 0.1737 0.8114 0.350 Uiso 1 1 calc R U . . .
C25 C -0.2885(10) 0.2185(11) 0.6817(6) 0.231(6) Uiso 1 1 d . . . . .
H25A H -0.2905 0.2230 0.6278 0.347 Uiso 1 1 calc R U . . .
H25B H -0.2423 0.2702 0.7078 0.347 Uiso 1 1 calc R U . . .
H25C H -0.3637 0.2244 0.6911 0.347 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 N5 2.063(3) . ?
Cu1 N1 2.064(3) . ?
Cu1 Cu2 2.4748(7) . ?
Cu1 Br1 2.5623(7) . ?
Cu1 Br2 2.5875(7) 2_656 ?
Cu2 N6 1.911(3) . ?
Cu2 N2 1.912(3) . ?
Cu2 Cu3 2.4767(7) . ?
Cu2 Br2 2.8443(8) 2_656 ?
Cu3 N7 1.902(3) . ?
Cu3 N3 1.904(3) . ?
Cu3 Cu4 2.4782(7) . ?
Cu4 N8 2.034(3) . ?
Cu4 N4 2.045(3) . ?
Cu4 Br1 2.5764(7) 2_646 ?
Cu4 Br2 2.7126(7) . ?
Br1 Cu4 2.5764(7) 2_656 ?
Br2 Cu1 2.5875(7) 2_646 ?
Br2 Cu2 2.8443(8) 2_646 ?
N1 C5 1.348(5) . ?
N1 C1 1.350(5) . ?
N2 C6 1.313(5) . ?
N2 C5 1.394(5) . ?
N3 C6 1.331(5) . ?
N3 C7 1.390(5) . ?
N4 C7 1.341(5) . ?
N4 C11 1.345(5) . ?
N5 C16 1.343(5) . ?
N5 C12 1.346(6) . ?
N6 C17 1.319(5) . ?
N6 C16 1.396(5) . ?
N7 C17 1.325(5) . ?
N7 C18 1.388(5) . ?
N8 C18 1.344(5) . ?
N8 C22 1.353(5) . ?
C1 C2 1.374(6) . ?
C1 H1A 0.9300 . ?
C2 C3 1.383(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.361(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.407(5) . ?
C4 H4A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.409(5) . ?
C8 C9 1.361(6) . ?
C8 H8A 0.9300 . ?
C9 C10 1.366(7) . ?
C9 H9A 0.9300 . ?
C10 C11 1.382(6) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.381(7) . ?
C12 H12A 0.9300 . ?
C13 C14 1.354(7) . ?
C13 H13A 0.9300 . ?
C14 C15 1.356(7) . ?
C14 H14A 0.9300 . ?
C15 C16 1.400(6) . ?
C15 H15A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 C19 1.413(5) . ?
C19 C20 1.370(6) . ?
C19 H19A 0.9300 . ?
C20 C21 1.370(7) . ?
C20 H20A 0.9300 . ?
C21 C22 1.384(6) . ?
C21 H21A 0.9300 . ?
C22 H22A 0.9300 . ?
O C23 1.383(16) . ?
N9 C25 1.293(13) . ?
N9 C23 1.319(11) . ?
N9 C24 1.392(8) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Cu1 N1 128.65(15) . . ?
N5 Cu1 Cu2 80.74(10) . . ?
N1 Cu1 Cu2 78.94(9) . . ?
N5 Cu1 Br1 106.45(10) . . ?
N1 Cu1 Br1 102.03(9) . . ?
Cu2 Cu1 Br1 168.91(3) . . ?
N5 Cu1 Br2 105.28(10) . 2_656 ?
N1 Cu1 Br2 109.90(9) . 2_656 ?
Cu2 Cu1 Br2 68.33(2) . 2_656 ?
Br1 Cu1 Br2 101.25(3) . 2_656 ?
N6 Cu2 N2 157.97(15) . . ?
N6 Cu2 Cu1 94.34(10) . . ?
N2 Cu2 Cu1 94.60(10) . . ?
N6 Cu2 Cu3 86.16(10) . . ?
N2 Cu2 Cu3 85.49(10) . . ?
Cu1 Cu2 Cu3 178.31(4) . . ?
N6 Cu2 Br2 101.08(11) . 2_656 ?
N2 Cu2 Br2 100.72(11) . 2_656 ?
Cu1 Cu2 Br2 57.72(2) . 2_656 ?
Cu3 Cu2 Br2 120.60(3) . 2_656 ?
N7 Cu3 N3 169.69(14) . . ?
N7 Cu3 Cu2 87.11(10) . . ?
N3 Cu3 Cu2 87.85(10) . . ?
N7 Cu3 Cu4 92.95(10) . . ?
N3 Cu3 Cu4 93.15(10) . . ?
Cu2 Cu3 Cu4 172.95(3) . . ?
N8 Cu4 N4 139.14(14) . . ?
N8 Cu4 Cu3 80.41(9) . . ?
N4 Cu4 Cu3 81.64(10) . . ?
N8 Cu4 Br1 101.72(10) . 2_646 ?
N4 Cu4 Br1 104.12(10) . 2_646 ?
Cu3 Cu4 Br1 166.58(3) . 2_646 ?
N8 Cu4 Br2 106.66(10) . . ?
N4 Cu4 Br2 100.67(10) . . ?
Cu3 Cu4 Br2 69.22(2) . . ?
Br1 Cu4 Br2 97.61(2) 2_646 . ?
Cu1 Br1 Cu4 81.95(2) . 2_656 ?
Cu1 Br2 Cu4 78.91(2) 2_646 . ?
Cu1 Br2 Cu2 53.957(18) 2_646 2_646 ?
Cu4 Br2 Cu2 132.87(2) . 2_646 ?
C5 N1 C1 118.2(3) . . ?
C5 N1 Cu1 128.5(3) . . ?
C1 N1 Cu1 113.2(3) . . ?
C6 N2 C5 120.0(3) . . ?
C6 N2 Cu2 122.0(3) . . ?
C5 N2 Cu2 117.8(3) . . ?
C6 N3 C7 120.4(3) . . ?
C6 N3 Cu3 119.0(3) . . ?
C7 N3 Cu3 119.8(3) . . ?
C7 N4 C11 118.1(3) . . ?
C7 N4 Cu4 126.7(3) . . ?
C11 N4 Cu4 115.0(3) . . ?
C16 N5 C12 118.3(4) . . ?
C16 N5 Cu1 128.1(3) . . ?
C12 N5 Cu1 113.6(3) . . ?
C17 N6 C16 119.5(3) . . ?
C17 N6 Cu2 121.2(3) . . ?
C16 N6 Cu2 119.2(2) . . ?
C17 N7 C18 120.8(3) . . ?
C17 N7 Cu3 120.4(3) . . ?
C18 N7 Cu3 118.7(3) . . ?
C18 N8 C22 117.9(3) . . ?
C18 N8 Cu4 126.7(3) . . ?
C22 N8 Cu4 115.1(3) . . ?
N1 C1 C2 123.6(4) . . ?
N1 C1 H1A 118.2 . . ?
C2 C1 H1A 118.2 . . ?
C1 C2 C3 117.9(4) . . ?
C1 C2 H2A 121.0 . . ?
C3 C2 H2A 121.0 . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 119.8(4) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
N1 C5 N2 114.8(3) . . ?
N1 C5 C4 120.6(4) . . ?
N2 C5 C4 124.5(4) . . ?
N2 C6 N3 121.6(3) . . ?
N2 C6 H6A 119.2 . . ?
N3 C6 H6A 119.2 . . ?
N4 C7 N3 116.3(3) . . ?
N4 C7 C8 120.5(4) . . ?
N3 C7 C8 123.1(4) . . ?
C9 C8 C7 119.9(4) . . ?
C9 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C8 C9 C10 119.8(4) . . ?
C8 C9 H9A 120.1 . . ?
C10 C9 H9A 120.1 . . ?
C9 C10 C11 117.9(4) . . ?
C9 C10 H10A 121.0 . . ?
C11 C10 H10A 121.0 . . ?
N4 C11 C10 123.7(4) . . ?
N4 C11 H11A 118.2 . . ?
C10 C11 H11A 118.2 . . ?
N5 C12 C13 123.2(5) . . ?
N5 C12 H12A 118.4 . . ?
C13 C12 H12A 118.4 . . ?
C14 C13 C12 117.9(5) . . ?
C14 C13 H13A 121.0 . . ?
C12 C13 H13A 121.0 . . ?
C13 C14 C15 120.4(5) . . ?
C13 C14 H14A 119.8 . . ?
C15 C14 H14A 119.8 . . ?
C14 C15 C16 119.9(5) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
N5 C16 N6 115.6(3) . . ?
N5 C16 C15 120.3(4) . . ?
N6 C16 C15 124.1(4) . . ?
N6 C17 N7 121.3(3) . . ?
N6 C17 H17A 119.4 . . ?
N7 C17 H17A 119.4 . . ?
N8 C18 N7 115.8(3) . . ?
N8 C18 C19 120.9(4) . . ?
N7 C18 C19 123.3(4) . . ?
C20 C19 C18 120.1(4) . . ?
C20 C19 H19A 120.0 . . ?
C18 C19 H19A 120.0 . . ?
C19 C20 C21 118.9(4) . . ?
C19 C20 H20A 120.5 . . ?
C21 C20 H20A 120.5 . . ?
C20 C21 C22 118.9(4) . . ?
C20 C21 H21A 120.6 . . ?
C22 C21 H21A 120.6 . . ?
N8 C22 C21 123.3(4) . . ?
N8 C22 H22A 118.4 . . ?
C21 C22 H22A 118.4 . . ?
C25 N9 C23 118.9(10) . . ?
C25 N9 C24 115.5(8) . . ?
C23 N9 C24 125.2(9) . . ?
N9 C23 O 107.5(9) . . ?
N9 C23 H23A 126.3 . . ?
O C23 H23A 126.3 . . ?
N9 C24 H24A 109.5 . . ?
N9 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N9 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N9 C25 H25A 109.5 . . ?
N9 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N9 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_refine_diff_density_max         1.031
_refine_diff_density_min         -0.731
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1981489'
loop_
_audit_author_name
_audit_author_address
'Jhy-Der Chen'
;Chung Yuan Christian University
Taiwan
;
_audit_update_record             
;
2020-02-03 deposited with the CCDC.	2020-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 Cu4 I2 N8'
_chemical_formula_weight         902.40

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.02250(10)
_cell_length_b                   8.3565(2)
_cell_length_c                   11.6598(2)
_cell_angle_alpha                87.6090(10)
_cell_angle_beta                 79.1280(10)
_cell_angle_gamma                72.9380(10)
_cell_volume                     642.32(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6780
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      28.26

_exptl_crystal_description       Plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.333
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    5.698
_shelx_estimated_absorpt_T_min   0.395
_shelx_estimated_absorpt_T_max   0.600
_exptl_absorpt_correction_type   multi_scan
_exptl_absorpt_correction_T_min  0.5386
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11499
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.779
_diffrn_reflns_theta_max         28.275
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3196
_reflns_number_gt                2577
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0182P)²+0.5628P] 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         3196
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0564
_refine_ls_wR_factor_gt          0.0525
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.27224(6) 0.36213(5) 0.23109(3) 0.03336(11) Uani 1 1 d . . . . .
Cu2 Cu 0.01458(7) 0.44021(5) 0.09998(4) 0.04409(13) Uani 1 1 d . . . . .
I I 0.66011(3) 0.34016(3) 0.23838(2) 0.03979(8) Uani 1 1 d . . . . .
N1 N 0.1092(4) 0.5749(3) 0.3111(2) 0.0278(6) Uani 1 1 d . . . . .
N2 N -0.0473(4) 0.6664(3) 0.1526(2) 0.0262(5) Uani 1 1 d . . . . .
N3 N -0.1468(4) 0.7701(3) -0.0201(2) 0.0267(5) Uani 1 1 d . . . . .
N4 N -0.2818(4) 0.8652(3) -0.1847(2) 0.0272(5) Uani 1 1 d . . . . .
C1 C 0.1400(5) 0.5983(4) 0.4192(3) 0.0355(7) Uani 1 1 d . . . . .
H1A H 0.2350 0.5139 0.4499 0.043 Uiso 1 1 calc R U . . .
C2 C 0.0397(6) 0.7389(4) 0.4859(3) 0.0410(8) Uani 1 1 d . . . . .
H2A H 0.0643 0.7497 0.5604 0.049 Uiso 1 1 calc R U . . .
C3 C -0.0992(6) 0.8641(4) 0.4391(3) 0.0409(8) Uani 1 1 d . . . . .
H3B H -0.1705 0.9612 0.4825 0.049 Uiso 1 1 calc R U . . .
C4 C -0.1325(5) 0.8460(4) 0.3290(3) 0.0336(7) Uani 1 1 d . . . . .
H4B H -0.2256 0.9308 0.2971 0.040 Uiso 1 1 calc R U . . .
C5 C -0.0254(4) 0.6990(4) 0.2649(3) 0.0275(6) Uani 1 1 d . . . . .
C6 C -0.1277(4) 0.7927(3) 0.0876(3) 0.0267(6) Uani 1 1 d . . . . .
H6A H -0.1720 0.9006 0.1191 0.032 Uiso 1 1 calc R U . . .
C7 C -0.2361(4) 0.9062(3) -0.0848(3) 0.0256(6) Uani 1 1 d . . . . .
C8 C -0.2794(5) 1.0754(4) -0.0530(3) 0.0321(7) Uani 1 1 d . . . . .
H8A H -0.2487 1.1037 0.0162 0.038 Uiso 1 1 calc R U . . .
C9 C -0.3669(5) 1.1983(4) -0.1241(3) 0.0371(8) Uani 1 1 d . . . . .
H9A H -0.3978 1.3102 -0.1025 0.045 Uiso 1 1 calc R U . . .
C10 C -0.4093(5) 1.1570(4) -0.2273(3) 0.0374(8) Uani 1 1 d . . . . .
H10A H -0.4659 1.2391 -0.2775 0.045 Uiso 1 1 calc R U . . .
C11 C -0.3646(5) 0.9891(4) -0.2537(3) 0.0338(7) Uani 1 1 d . . . . .
H11A H -0.3935 0.9598 -0.3232 0.041 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 1.971(2) . ?
Cu1 N4 1.975(2) 2_565 ?
Cu1 Cu2 2.5108(6) . ?
Cu1 I 2.6931(5) . ?
Cu2 N2 1.911(2) . ?
Cu2 N3 1.916(2) 2_565 ?
Cu2 Cu2 2.5183(9) 2_565 ?
Cu2 I 3.0155(6) 1_455 ?
I Cu2 3.0155(6) 1_655 ?
N1 C1 1.349(4) . ?
N1 C5 1.352(4) . ?
N2 C6 1.323(4) . ?
N2 C5 1.394(4) . ?
N3 C6 1.316(4) . ?
N3 C7 1.395(4) . ?
N3 Cu2 1.916(2) 2_565 ?
N4 C11 1.345(4) . ?
N4 C7 1.348(4) . ?
N4 Cu1 1.975(2) 2_565 ?
C1 C2 1.366(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.377(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.371(4) . ?
C3 H3B 0.9300 . ?
C4 C5 1.399(4) . ?
C4 H4B 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.406(4) . ?
C8 C9 1.367(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.373(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.380(4) . ?
C10 H10A 0.9300 . ?
C11 H11A 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 N4 147.17(10) . 2_565 ?
N1 Cu1 Cu2 83.43(7) . . ?
N4 Cu1 Cu2 81.21(7) 2_565 . ?
N1 Cu1 I 105.55(7) . . ?
N4 Cu1 I 104.31(7) 2_565 . ?
Cu2 Cu1 I 142.43(2) . . ?
N2 Cu2 N3 162.52(11) . 2_565 ?
N2 Cu2 Cu1 87.71(7) . . ?
N3 Cu2 Cu1 88.14(7) 2_565 . ?
N2 Cu2 Cu2 86.23(8) . 2_565 ?
N3 Cu2 Cu2 85.70(8) 2_565 2_565 ?
Cu1 Cu2 Cu2 138.62(4) . 2_565 ?
N2 Cu2 I 100.97(8) . 1_455 ?
N3 Cu2 I 96.51(8) 2_565 1_455 ?
Cu1 Cu2 I 103.155(19) . 1_455 ?
Cu2 Cu2 I 118.19(3) 2_565 1_455 ?
Cu1 I Cu2 140.318(15) . 1_655 ?
C1 N1 C5 118.3(3) . . ?
C1 N1 Cu1 116.6(2) . . ?
C5 N1 Cu1 125.1(2) . . ?
C6 N2 C5 119.2(2) . . ?
C6 N2 Cu2 120.8(2) . . ?
C5 N2 Cu2 119.74(19) . . ?
C6 N3 C7 120.1(2) . . ?
C6 N3 Cu2 121.00(19) . 2_565 ?
C7 N3 Cu2 118.07(19) . 2_565 ?
C11 N4 C7 118.5(3) . . ?
C11 N4 Cu1 115.3(2) . 2_565 ?
C7 N4 Cu1 125.6(2) . 2_565 ?
N1 C1 C2 123.8(3) . . ?
N1 C1 H1A 118.1 . . ?
C2 C1 H1A 118.1 . . ?
C1 C2 C3 117.7(3) . . ?
C1 C2 H2A 121.1 . . ?
C3 C2 H2A 121.1 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3B 119.9 . . ?
C2 C3 H3B 119.9 . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 H4B 120.3 . . ?
C5 C4 H4B 120.3 . . ?
N1 C5 N2 115.0(2) . . ?
N1 C5 C4 120.5(3) . . ?
N2 C5 C4 124.5(3) . . ?
N3 C6 N2 121.9(2) . . ?
N3 C6 H6A 119.0 . . ?
N2 C6 H6A 119.0 . . ?
N4 C7 N3 114.7(2) . . ?
N4 C7 C8 120.1(3) . . ?
N3 C7 C8 125.2(3) . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8A 120.1 . . ?
C7 C8 H8A 120.1 . . ?
C8 C9 C10 120.2(3) . . ?
C8 C9 H9A 119.9 . . ?
C10 C9 H9A 119.9 . . ?
C9 C10 C11 117.4(3) . . ?
C9 C10 H10A 121.3 . . ?
C11 C10 H10A 121.3 . . ?
N4 C11 C10 123.8(3) . . ?
N4 C11 H11A 118.1 . . ?
C10 C11 H11A 118.1 . . ?

_refine_diff_density_max         0.869
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.100

