# Electronic Supplementary Material (ESI) for Materials Horizons.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_210808a
_audit_block_doi                 10.5517/ccdc.csd.cc2gyn36
_database_code_depnum_ccdc_archive 'CCDC 2292608'
loop_
_audit_author_name
_audit_author_address
'Guorong Lei'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-09-04 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H4 Br2 Cu N8 O6'
_chemical_formula_weight         483.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   9.3556(9)
_cell_length_b                   6.8168(7)
_cell_length_c                   9.3773(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.497(2)
_cell_angle_gamma                90.00
_cell_volume                     596.93(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2328
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      28.295

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.690
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             462
_exptl_absorpt_coefficient_mu    8.571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3076
_exptl_absorpt_correction_T_max  0.5853
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2734
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         25.01
_reflns_number_total             1055
_reflns_number_gt                973
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker 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)+(0.0738P)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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1055
_refine_ls_number_parameters     98
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.0984
_refine_ls_wR_factor_gt          0.0969
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.5000 0.0000 0.0137(3) Uani 1 2 d S . .
Br1 Br 0.65770(4) 0.19068(6) 0.23607(4) 0.0163(3) Uani 1 1 d . . .
N1 N 0.6849(4) 0.6407(6) 0.0259(4) 0.0172(8) Uani 1 1 d . . .
N2 N 0.7950(4) 0.5723(6) 0.1213(4) 0.0245(9) Uani 1 1 d . . .
N3 N 0.8678(4) 0.8289(5) 0.0057(4) 0.0178(9) Uani 1 1 d . . .
N4 N 0.9414(4) 0.9931(6) -0.0357(4) 0.0195(8) Uani 1 1 d . . .
O1 O 0.6133(4) 0.2051(5) 0.0638(3) 0.0245(8) Uani 1 1 d . . .
O2 O 0.5269(3) 0.0414(5) 0.2895(3) 0.0208(7) Uani 1 1 d . . .
O3 O 0.8038(3) 0.0595(6) 0.2517(4) 0.0298(9) Uani 1 1 d . . .
C1 C 0.9031(5) 0.6887(7) 0.1077(5) 0.0241(12) Uani 1 1 d . . .
H1 H 0.9910 0.6789 0.1590 0.029 Uiso 1 1 calc R . .
C2 C 0.7289(4) 0.7938(6) -0.0408(5) 0.0152(9) Uani 1 1 d . . .
H2 H 0.6753 0.8670 -0.1085 0.018 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0103(4) 0.0170(5) 0.0134(4) 0.0000(3) -0.0025(3) -0.0059(3)
Br1 0.0147(3) 0.0177(4) 0.0160(3) -0.00042(15) -0.00299(19) -0.00098(16)
N1 0.0116(16) 0.024(2) 0.0155(19) 0.0008(16) -0.0053(14) -0.0038(15)
N2 0.0180(19) 0.028(2) 0.026(2) 0.0097(18) -0.0101(15) -0.0065(17)
N3 0.0130(17) 0.020(2) 0.020(2) 0.0024(15) -0.0023(15) -0.0098(14)
N4 0.0186(17) 0.019(2) 0.021(2) -0.0001(15) -0.0021(14) -0.0103(16)
O1 0.0282(17) 0.029(2) 0.0159(17) 0.0031(14) -0.0037(14) 0.0016(14)
O2 0.0187(15) 0.0262(18) 0.0170(16) 0.0018(14) -0.0024(12) -0.0075(13)
O3 0.0160(16) 0.038(2) 0.034(2) 0.0000(17) -0.0037(14) 0.0054(15)
C1 0.015(2) 0.027(3) 0.029(3) 0.006(2) -0.010(2) -0.0037(18)
C2 0.013(2) 0.016(2) 0.016(2) 0.0006(17) -0.0058(16) -0.0039(16)

_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 1.980(4) . ?
Cu1 N1 1.980(4) 3_665 ?
Cu1 O2 2.025(3) 4_565 ?
Cu1 O2 2.025(3) 2_655 ?
Cu1 O1 2.333(3) . ?
Cu1 O1 2.333(3) 3_665 ?
Br1 O3 1.633(3) . ?
Br1 O1 1.646(3) . ?
Br1 O2 1.691(3) . ?
N1 C2 1.297(6) . ?
N1 N2 1.402(5) . ?
N2 C1 1.297(6) . ?
N3 C2 1.366(6) . ?
N3 C1 1.378(6) . ?
N3 N4 1.382(5) . ?
N4 N4 1.253(7) 3_775 ?
O2 Cu1 2.025(3) 2_645 ?
C1 H1 0.9300 . ?
C2 H2 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 N1 180.0 . 3_665 ?
N1 Cu1 O2 91.57(14) . 4_565 ?
N1 Cu1 O2 88.43(14) 3_665 4_565 ?
N1 Cu1 O2 88.43(14) . 2_655 ?
N1 Cu1 O2 91.57(14) 3_665 2_655 ?
O2 Cu1 O2 180.0 4_565 2_655 ?
N1 Cu1 O1 90.35(15) . . ?
N1 Cu1 O1 89.65(15) 3_665 . ?
O2 Cu1 O1 92.77(11) 4_565 . ?
O2 Cu1 O1 87.23(11) 2_655 . ?
N1 Cu1 O1 89.65(15) . 3_665 ?
N1 Cu1 O1 90.35(15) 3_665 3_665 ?
O2 Cu1 O1 87.23(11) 4_565 3_665 ?
O2 Cu1 O1 92.77(11) 2_655 3_665 ?
O1 Cu1 O1 180.0 . 3_665 ?
O3 Br1 O1 106.31(17) . . ?
O3 Br1 O2 105.12(18) . . ?
O1 Br1 O2 100.53(16) . . ?
C2 N1 N2 109.4(3) . . ?
C2 N1 Cu1 129.2(3) . . ?
N2 N1 Cu1 121.3(3) . . ?
C1 N2 N1 106.3(4) . . ?
C2 N3 C1 106.5(4) . . ?
C2 N3 N4 122.2(4) . . ?
C1 N3 N4 130.8(4) . . ?
N4 N4 N3 110.2(5) 3_775 . ?
Br1 O1 Cu1 112.73(16) . . ?
Br1 O2 Cu1 120.52(17) . 2_645 ?
N2 C1 N3 109.7(4) . . ?
N2 C1 H1 125.2 . . ?
N3 C1 H1 125.2 . . ?
N1 C2 N3 108.1(4) . . ?
N1 C2 H2 126.0 . . ?
N3 C2 H2 126.0 . . ?

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
N1 Cu1 N1 C2 -147(100) 3_665 . . . ?
O2 Cu1 N1 C2 55.6(4) 4_565 . . . ?
O2 Cu1 N1 C2 -124.4(4) 2_655 . . . ?
O1 Cu1 N1 C2 148.4(4) . . . . ?
O1 Cu1 N1 C2 -31.6(4) 3_665 . . . ?
N1 Cu1 N1 N2 37(100) 3_665 . . . ?
O2 Cu1 N1 N2 -120.3(3) 4_565 . . . ?
O2 Cu1 N1 N2 59.7(3) 2_655 . . . ?
O1 Cu1 N1 N2 -27.6(3) . . . . ?
O1 Cu1 N1 N2 152.4(3) 3_665 . . . ?
C2 N1 N2 C1 -0.2(5) . . . . ?
Cu1 N1 N2 C1 176.5(3) . . . . ?
C2 N3 N4 N4 170.7(4) . . . 3_775 ?
C1 N3 N4 N4 0.1(8) . . . 3_775 ?
O3 Br1 O1 Cu1 -148.05(19) . . . . ?
O2 Br1 O1 Cu1 102.63(19) . . . . ?
N1 Cu1 O1 Br1 73.61(19) . . . . ?
N1 Cu1 O1 Br1 -106.39(19) 3_665 . . . ?
O2 Cu1 O1 Br1 165.21(19) 4_565 . . . ?
O2 Cu1 O1 Br1 -14.79(19) 2_655 . . . ?
O1 Cu1 O1 Br1 -25(100) 3_665 . . . ?
O3 Br1 O2 Cu1 80.1(2) . . . 2_645 ?
O1 Br1 O2 Cu1 -169.68(19) . . . 2_645 ?
N1 N2 C1 N3 -0.7(5) . . . . ?
C2 N3 C1 N2 1.3(5) . . . . ?
N4 N3 C1 N2 173.0(4) . . . . ?
N2 N1 C2 N3 1.0(5) . . . . ?
Cu1 N1 C2 N3 -175.3(3) . . . . ?
C1 N3 C2 N1 -1.4(5) . . . . ?
N4 N3 C2 N1 -174.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.814
_refine_diff_density_min         -1.553
_refine_diff_density_rms         0.192
