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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_a
_database_code_depnum_ccdc_archive 'CCDC 2290231'
loop_
_audit_author_name
_audit_author_address
'Nagesh Manurkar'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-08-23 deposited with the CCDC.	2024-01-19 downloaded from the CCDC.
;
_audit_creation_date             2023-08-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H8 Cu F N O4'
_chemical_formula_sum            'C9 H8 Cu F N O4'
_chemical_formula_weight         276.70
_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'
F F 0.0171 0.0103 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   7.1182(12)
_cell_length_b                   22.582(4)
_cell_length_c                   5.9936(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.469(5)
_cell_angle_gamma                90
_cell_volume                     936.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4491
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      29.192
_cell_measurement_theta_min      2.942
_shelx_estimated_absorpt_T_max   0.799
_shelx_estimated_absorpt_T_min   0.540
_exptl_absorpt_coefficient_mu    2.344
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1359 before and 0.0462 after correction.
The Ratio of minimum to maximum transmission is 0.8116.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic whiteish black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.962
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            12871
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.674
_diffrn_reflns_theta_min         1.804
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           35.0
_diffrn_source_power             1.575
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2300
_reflns_number_total             2914
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2914
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.058
_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)+(0.0364P)²+0.2963P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0780
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 Cu01-H00A \\sim Cu01-H00B
 with sigma of 0.02
3.a Free rotating group:
 O004(H00A,H00B)
3.b Secondary CH2 refined with riding coordinates:
 C009(H00C,H00D)
3.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C00D(H00E), C00F(H00F), C00G(H00G)
;
_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
Cu01 Cu 0.16922(3) 0.30610(2) 0.05419(4) 0.02454(8) Uani 1 1 d D . . . .
O002 O 0.29662(18) 0.28223(6) -0.1887(2) 0.0257(3) Uani 1 1 d . . . . .
O003 O 0.03320(19) 0.34031(6) 0.2633(2) 0.0290(3) Uani 1 1 d . . . . .
O004 O -0.06323(19) 0.26001(6) -0.0642(2) 0.0282(3) Uani 1 1 d G . . . .
H00A H -0.0471 0.2276 -0.1293 0.042 Uiso 1 1 d DG U . . .
H00B H -0.1598 0.2761 -0.1544 0.042 Uiso 1 1 d DG U . . .
O005 O 0.5778(2) 0.29046(7) -0.2895(3) 0.0342(3) Uani 1 1 d . . . . .
F006 F 0.2717(3) 0.50588(7) 0.9370(3) 0.0608(4) Uani 1 1 d . . . . .
N007 N 0.3927(2) 0.35484(7) 0.1611(3) 0.0237(3) Uani 1 1 d . . . . .
C008 C 0.4180(3) 0.39382(8) 0.3201(3) 0.0259(4) Uani 1 1 d . . . . .
H008 H 0.5344 0.4144 0.3519 0.031 Uiso 1 1 calc R U . . .
C009 C 0.5445(3) 0.34275(9) 0.0391(3) 0.0271(4) Uani 1 1 d . . . . .
H00C H 0.6540 0.3244 0.1430 0.033 Uiso 1 1 calc R U . . .
H00D H 0.5877 0.3797 -0.0150 0.033 Uiso 1 1 calc R U . . .
C00A C 0.2800(3) 0.40844(8) 0.4544(3) 0.0248(4) Uani 1 1 d . . . . .
C00B C 0.4691(3) 0.30192(8) -0.1633(3) 0.0249(4) Uani 1 1 d . . . . .
C00C C 0.0981(3) 0.38037(8) 0.4234(3) 0.0253(4) Uani 1 1 d . . . . .
C00D C 0.3360(3) 0.45079(9) 0.6308(4) 0.0332(4) Uani 1 1 d . . . . .
H00E H 0.4560 0.4691 0.6534 0.040 Uiso 1 1 calc R U . . .
C00E C 0.2152(4) 0.46464(10) 0.7667(4) 0.0381(5) Uani 1 1 d . . . . .
C00F C -0.0192(3) 0.39555(9) 0.5749(4) 0.0334(4) Uani 1 1 d . . . . .
H00F H -0.1376 0.3767 0.5602 0.040 Uiso 1 1 calc R U . . .
C00G C 0.0370(3) 0.43746(10) 0.7436(4) 0.0391(5) Uani 1 1 d . . . . .
H00G H -0.0430 0.4474 0.8404 0.047 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
Cu01 O002 1.9616(13) . ?
Cu01 O003 1.9156(13) . ?
Cu01 O004 1.9436(14) . ?
Cu01 N007 1.9178(16) . ?
O002 C00B 1.281(2) . ?
O003 C00C 1.322(2) . ?
O004 H00A 0.8499 . ?
O004 H00B 0.8502 . ?
O005 C00B 1.229(2) . ?
F006 C00E 1.371(2) . ?
N007 C008 1.279(2) . ?
N007 C009 1.464(2) . ?
C008 H008 0.9300 . ?
C008 C00A 1.446(3) . ?
C009 H00C 0.9700 . ?
C009 H00D 0.9700 . ?
C009 C00B 1.519(3) . ?
C00A C00C 1.414(3) . ?
C00A C00D 1.412(3) . ?
C00C C00F 1.411(3) . ?
C00D H00E 0.9300 . ?
C00D C00E 1.352(3) . ?
C00E C00G 1.387(3) . ?
C00F H00F 0.9300 . ?
C00F C00G 1.375(3) . ?
C00G H00G 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
O003 Cu01 O002 171.06(6) . . ?
O003 Cu01 O004 86.43(6) . . ?
O003 Cu01 N007 93.23(6) . . ?
O004 Cu01 O002 94.77(6) . . ?
N007 Cu01 O002 85.12(6) . . ?
N007 Cu01 O004 177.09(6) . . ?
C00B O002 Cu01 114.33(12) . . ?
C00C O003 Cu01 127.36(12) . . ?
Cu01 O004 H00A 115.8 . . ?
Cu01 O004 H00B 119.8 . . ?
H00A O004 H00B 104.5 . . ?
C008 N007 Cu01 127.28(14) . . ?
C008 N007 C009 120.55(16) . . ?
C009 N007 Cu01 112.16(12) . . ?
N007 C008 H008 117.4 . . ?
N007 C008 C00A 125.17(18) . . ?
C00A C008 H008 117.4 . . ?
N007 C009 H00C 109.6 . . ?
N007 C009 H00D 109.6 . . ?
N007 C009 C00B 110.32(15) . . ?
H00C C009 H00D 108.1 . . ?
C00B C009 H00C 109.6 . . ?
C00B C009 H00D 109.6 . . ?
C00C C00A C008 123.00(17) . . ?
C00D C00A C008 117.45(18) . . ?
C00D C00A C00C 119.48(18) . . ?
O002 C00B C009 117.17(16) . . ?
O005 C00B O002 125.23(18) . . ?
O005 C00B C009 117.60(17) . . ?
O003 C00C C00A 123.80(17) . . ?
O003 C00C C00F 118.33(17) . . ?
C00F C00C C00A 117.86(18) . . ?
C00A C00D H00E 120.0 . . ?
C00E C00D C00A 119.9(2) . . ?
C00E C00D H00E 120.0 . . ?
F006 C00E C00G 118.5(2) . . ?
C00D C00E F006 119.3(2) . . ?
C00D C00E C00G 122.2(2) . . ?
C00C C00F H00F 119.1 . . ?
C00G C00F C00C 121.7(2) . . ?
C00G C00F H00F 119.1 . . ?
C00E C00G H00G 120.6 . . ?
C00F C00G C00E 118.7(2) . . ?
C00F C00G H00G 120.6 . . ?

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
Cu01 O002 C00B O005 176.85(16) . . . . ?
Cu01 O002 C00B C009 -3.2(2) . . . . ?
Cu01 O003 C00C C00A 5.2(3) . . . . ?
Cu01 O003 C00C C00F -173.86(14) . . . . ?
Cu01 N007 C008 C00A 0.7(3) . . . . ?
Cu01 N007 C009 C00B 9.00(19) . . . . ?
O003 C00C C00F C00G -179.0(2) . . . . ?
F006 C00E C00G C00F -179.2(2) . . . . ?
N007 C008 C00A C00C 0.1(3) . . . . ?
N007 C008 C00A C00D 177.05(19) . . . . ?
N007 C009 C00B O002 -3.8(2) . . . . ?
N007 C009 C00B O005 176.12(17) . . . . ?
C008 N007 C009 C00B -171.52(17) . . . . ?
C008 C00A C00C O003 -3.2(3) . . . . ?
C008 C00A C00C C00F 175.85(18) . . . . ?
C008 C00A C00D C00E -177.8(2) . . . . ?
C009 N007 C008 C00A -178.70(18) . . . . ?
C00A C00C C00F C00G 1.9(3) . . . . ?
C00A C00D C00E F006 -179.9(2) . . . . ?
C00A C00D C00E C00G 1.7(4) . . . . ?
C00C C00A C00D C00E -0.7(3) . . . . ?
C00C C00F C00G C00E -1.1(3) . . . . ?
C00D C00A C00C O003 179.94(18) . . . . ?
C00D C00A C00C C00F -1.0(3) . . . . ?
C00D C00E C00G C00F -0.8(4) . . . . ?


_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 2290233'
loop_
_audit_author_name
_audit_author_address
'Nagesh Manurkar'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-08-23 deposited with the CCDC.	2024-01-19 downloaded from the CCDC.
;
_audit_creation_date             2023-08-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_formula_moiety         'C9 H6 Cu I N O3'
_chemical_formula_sum            'C9 H6 Cu I N O3'
_chemical_formula_weight         366.603
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu 0.34125 1.28947 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19100 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07120 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -y,x-y,z
3 -x+y,-x,z
4 -x,-y,-z
5 y,-x+y,-z
6 x-y,x,-z
7 x+1/3,y+2/3,z+2/3
8 -y+1/3,x-y+2/3,z+2/3
9 -x+y+1/3,-x+2/3,z+2/3
10 -x+1/3,-y+2/3,-z+2/3
11 y+1/3,-x+y+2/3,-z+2/3
12 x-y+1/3,x+2/3,-z+2/3
13 x+2/3,y+1/3,z+1/3
14 -y+2/3,x-y+1/3,z+1/3
15 -x+y+2/3,-x+1/3,z+1/3
16 -x+2/3,-y+1/3,-z+1/3
17 y+2/3,-x+y+1/3,-z+1/3
18 x-y+2/3,x+1/3,-z+1/3

_symmetry_Int_Tables_number      148
_cell_length_a                   26.796(5)
_cell_length_b                   26.796(5)
_cell_length_c                   7.4941(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4660.1(15)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    5905
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.24
_cell_measurement_theta_min      2.63
_exptl_absorpt_coefficient_mu    5.073
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'metallic whiteish green'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    2.351
_exptl_crystal_description       block
_exptl_crystal_F_000             3115.115
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 1.0000
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17322
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 1.0000
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.74
_diffrn_reflns_theta_min         1.52
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              28
_reflns_limit_h_min              0
_reflns_limit_k_max              29
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              -9
_reflns_number_gt                1913
_reflns_number_total             2216
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_diff_density_max         2.4086
_refine_diff_density_min         -1.8785
_refine_diff_density_rms         0.1462
_refine_ls_d_res_high            0.7898
_refine_ls_d_res_low             13.3981
_refine_ls_goodness_of_fit_ref   1.0450
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    11
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.0450
_refine_ls_shift/su_max          0.0314
_refine_ls_shift/su_mean         0.0088
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²+50.5488P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0845
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C2(H2), C9(H9)
;
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_refinement_flags_posn
I1 I 0.449365(17) 0.668269(14) 1.03974(5) 0.04572(14) Uani 1.000000 .
Cu1 Cu 0.67774(2) 0.88949(2) 0.42091(6) 0.02042(14) Uani 1.000000 .
C7 C 0.7007(2) 0.96521(18) 0.7147(6) 0.0272(9) Uani 1.000000 .
H7a H 0.7256(2) 0.96804(18) 0.8129(6) 0.0326(11) Uiso 1.000000 R
H7b H 0.6767(2) 0.98073(18) 0.7541(6) 0.0326(11) Uiso 1.000000 R
C3 C 0.5449(2) 0.7242(2) 0.5486(6) 0.0333(11) Uani 1.000000 .
H3 H 0.5419(2) 0.7064(2) 0.4395(6) 0.0400(13) Uiso 1.000000 R
C4 C 0.58937(18) 0.78067(17) 0.5749(5) 0.0212(8) Uani 1.000000 .
C5 C 0.59100(17) 0.80802(18) 0.7388(5) 0.0207(8) Uani 1.000000 .
C6 C 0.63001(18) 0.86831(18) 0.7769(5) 0.0224(8) Uani 1.000000 .
H6 H 0.63004(18) 0.88131(18) 0.8920(5) 0.0269(10) Uiso 1.000000 R
C1 C 0.5093(2) 0.71972(19) 0.8451(6) 0.0316(10) Uani 1.000000 .
C8 C 0.73704(18) 0.99972(18) 0.5570(6) 0.0249(9) Uani 1.000000 .
C2 C 0.5052(2) 0.6942(2) 0.6805(7) 0.0362(11) Uani 1.000000 .
H2 H 0.4756(2) 0.6567(2) 0.6592(7) 0.0435(13) Uiso 1.000000 R
O1 O 0.62830(13) 0.80738(12) 0.4463(4) 0.0220(6) Uani 1.000000 .
O2 O 0.73185(15) 0.97154(13) 0.4146(4) 0.0323(7) Uani 1.000000 .
O3 O 0.61693(16) 0.89802(15) 0.2357(5) 0.0382(8) Uani 1.000000 .
C9 C 0.5511(2) 0.77591(19) 0.8752(6) 0.0268(9) Uani 1.000000 .
H9 H 0.5532(2) 0.79293(19) 0.9851(6) 0.0321(11) Uiso 1.000000 R
N1 N 0.66434(15) 0.90481(14) 0.6634(4) 0.0208(7) Uani 1.000000 .


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
I1 C1 2.096(4) . ?
Cu1 Cu1 3.0574(10) 10_665 ?
Cu1 O1 1.928(3) . ?
Cu1 O1 2.010(3) 10_665 ?
Cu1 O2 1.937(3) . ?
Cu1 O3 2.238(3) . ?
Cu1 N1 1.936(3) . ?
C7 H7a 0.9700 . ?
C7 H7b 0.9700 . ?
C7 C8 1.517(6) . ?
C7 N1 1.463(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.395(6) . ?
C3 C2 1.378(7) . ?
C4 C5 1.419(6) . ?
C4 O1 1.335(5) . ?
C5 C6 1.448(6) . ?
C5 C9 1.417(6) . ?
C6 H6 0.9300 . ?
C6 N1 1.276(5) . ?
C1 C2 1.388(7) . ?
C1 C9 1.373(6) . ?
C8 O2 1.274(5) . ?
C8 O3 1.230(5) 14_665 ?
C2 H2 0.9300 . ?
C9 H9 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
O2 Cu1 O1 174.35(14) . . ?
O2 Cu1 O1 102.84(12) . 10_665 ?
O3 Cu1 O1 93.32(13) . . ?
O3 Cu1 O1 90.43(13) . 10_665 ?
O3 Cu1 O2 92.23(14) . . ?
N1 Cu1 O1 93.15(13) . . ?
N1 Cu1 O1 158.53(13) . 10_665 ?
N1 Cu1 O2 83.98(14) . . ?
N1 Cu1 O3 109.82(14) . . ?
H7b C7 H7a 108.2 . . ?
C8 C7 H7a 109.7(2) . . ?
C8 C7 H7b 109.7(2) . . ?
N1 C7 H7a 109.7(2) . . ?
N1 C7 H7b 109.7(2) . . ?
N1 C7 C8 109.8(3) . . ?
C4 C3 H3 119.2(3) . . ?
C2 C3 H3 119.2(3) . . ?
C2 C3 C4 121.5(4) . . ?
C5 C4 C3 118.1(4) . . ?
O1 C4 C3 119.6(4) . . ?
O1 C4 C5 122.3(4) . . ?
C6 C5 C4 124.5(4) . . ?
C9 C5 C4 119.4(4) . . ?
C9 C5 C6 116.1(4) . . ?
H6 C6 C5 117.8(2) . . ?
N1 C6 C5 124.4(4) . . ?
N1 C6 H6 117.8(2) . . ?
C2 C1 I1 116.6(3) . . ?
C9 C1 I1 122.9(3) . . ?
C9 C1 C2 120.5(4) . . ?
O2 C8 C7 116.4(4) . . ?
O3 C8 C7 120.4(4) 14_665 . ?
O3 C8 O2 123.2(4) 14_665 . ?
C1 C2 C3 120.1(4) . . ?
H2 C2 C3 119.9(3) . . ?
H2 C2 C1 119.9(3) . . ?
C4 O1 Cu1 126.1(2) . . ?
C4 O1 Cu1 131.9(2) . 10_665 ?
C8 O2 Cu1 116.8(3) . . ?
C8 O3 Cu1 136.2(3) 9_564 . ?
C1 C9 C5 120.1(4) . . ?
H9 C9 C5 120.0(2) . . ?
H9 C9 C1 120.0(3) . . ?
C7 N1 Cu1 113.0(3) . . ?
C6 N1 Cu1 127.1(3) . . ?
C6 N1 C7 119.9(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
I1 C1 C2 C3 -176.7(4) . . . . ?
I1 C1 C9 C5 178.8(3) . . . . ?
Cu1 O1 C4 C3 159.9(4) . . . . ?
Cu1 O1 C4 C3 -24.9(4) 10_665 . . . ?
Cu1 O1 C4 C5 155.9(3) 10_665 . . . ?
Cu1 O1 C4 C5 -19.2(3) . . . . ?
Cu1 O2 C8 C7 0.8(4) . . . . ?
Cu1 O2 C8 O3 -177.8(3) . . . 14_665 ?
Cu1 O3 C8 C7 -16.3(5) . . 9_564 9_564 ?
Cu1 O3 C8 O2 162.3(4) . . 9_564 9_564 ?
Cu1 N1 C7 C8 2.8(3) . . . . ?
Cu1 N1 C6 C5 -4.7(4) . . . . ?
C7 N1 C6 C5 178.0(4) . . . . ?
C3 C4 C5 C6 -172.2(4) . . . . ?
C3 C4 C5 C9 5.6(5) . . . . ?
C3 C2 C1 C9 3.3(6) . . . . ?
C4 C5 C6 N1 5.7(5) . . . . ?
C4 C5 C9 C1 -3.4(5) . . . . ?
C5 C9 C1 C2 -1.1(5) . . . . ?


_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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2290232'
loop_
_audit_author_name
_audit_author_address
'Nagesh Manurkar'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-08-23 deposited with the CCDC.	2024-01-19 downloaded from the CCDC.
;
_audit_creation_date             2023-08-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_formula_moiety         'C9 H6 Br Cu N O3, 0.056(O)'
_chemical_formula_sum            'C9 H6 Br Cu N O3.056'
_chemical_formula_weight         320.491
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95570 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu 0.34125 1.28947 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19100 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -y,x-y,z
3 -x+y,-x,z
4 -x,-y,-z
5 y,-x+y,-z
6 x-y,x,-z
7 x+1/3,y+2/3,z+2/3
8 -y+1/3,x-y+2/3,z+2/3
9 -x+y+1/3,-x+2/3,z+2/3
10 -x+1/3,-y+2/3,-z+2/3
11 y+1/3,-x+y+2/3,-z+2/3
12 x-y+1/3,x+2/3,-z+2/3
13 x+2/3,y+1/3,z+1/3
14 -y+2/3,x-y+1/3,z+1/3
15 -x+y+2/3,-x+1/3,z+1/3
16 -x+2/3,-y+1/3,-z+1/3
17 y+2/3,-x+y+1/3,-z+1/3
18 x-y+2/3,x+1/3,-z+1/3

_symmetry_Int_Tables_number      148
_cell_length_a                   26.8602(6)
_cell_length_b                   26.8602(6)
_cell_length_c                   7.2007(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4499.1(3)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    3215
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.97
_cell_measurement_theta_min      2.63
_exptl_absorpt_coefficient_mu    6.163
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'metallic whiteish green'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    2.129
_exptl_crystal_description       block
_exptl_crystal_F_000             2802.560
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_Laue_measured_fraction_full 0.9994
_diffrn_reflns_Laue_measured_fraction_max 0.9994
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20814
_diffrn_reflns_point_group_measured_fraction_full 0.9994
_diffrn_reflns_point_group_measured_fraction_max 0.9994
_diffrn_reflns_theta_full        25.0472
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.63
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              27
_reflns_limit_h_min              0
_reflns_limit_k_max              27
_reflns_limit_k_min              0
_reflns_limit_l_max              8
_reflns_limit_l_min              -8
_reflns_number_gt                1457
_reflns_number_total             1773
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_diff_density_max         1.5505
_refine_diff_density_min         -1.1734
_refine_diff_density_rms         0.1401
_refine_ls_d_res_high            0.8394
_refine_ls_d_res_low             7.7539
_refine_ls_goodness_of_fit_ref   1.0462
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    11
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1773
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.0462
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0477P)²+31.5927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0931
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: O5(0.05556)
3.a Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C7(H7)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Br1 Br 0.01062(2) 0.88959(3) 0.61255(9) 0.0505(2) Uani 1.000000 1 . . .
Cu1 Cu 0.22232(2) 0.87736(2) 1.24141(7) 0.02012(18) Uani 1.000000 1 . . .
O1 O 0.14015(12) 0.84559(12) 1.2146(4) 0.0217(7) Uani 1.000000 1 . . .
O2 O 0.30409(13) 0.90495(15) 1.2494(4) 0.0307(8) Uani 1.000000 1 . . .
O3 O 0.38470(14) 0.94783(16) 1.0881(5) 0.0369(9) Uani 1.000000 1 . . .
N1 N 0.23821(15) 0.90686(15) 0.9910(5) 0.0194(8) Uani 1.000000 1 . . .
C1 C 0.11045(19) 0.89468(19) 0.7720(7) 0.0259(10) Uani 1.000000 1 . . .
H1 H 0.12781(19) 0.91003(19) 0.6583(7) 0.0311(12) Uiso 1.000000 1 R . .
C2 C 0.0548(2) 0.8808(2) 0.8016(7) 0.0307(11) Uani 1.000000 1 . . .
C3 C 0.0287(2) 0.8587(2) 0.9717(7) 0.0361(13) Uani 1.000000 1 . . .
H3 H -0.0086(2) 0.8511(2) 0.9930(7) 0.0433(15) Uiso 1.000000 1 R . .
C4 C 0.0579(2) 0.8482(2) 1.1087(7) 0.0308(11) Uani 1.000000 1 . . .
H4 H 0.0397(2) 0.8332(2) 1.2216(7) 0.0370(13) Uiso 1.000000 1 R . .
C5 C 0.11399(19) 0.85940(18) 1.0827(6) 0.0201(9) Uani 1.000000 1 . . .
C6 C 0.14199(19) 0.88586(18) 0.9134(6) 0.0206(9) Uani 1.000000 1 . . .
C7 C 0.20170(19) 0.90616(19) 0.8727(6) 0.0230(10) Uani 1.000000 1 . . .
H7 H 0.21477(19) 0.91963(19) 0.7534(6) 0.0276(12) Uiso 1.000000 1 R . .
C8 C 0.29841(19) 0.9297(2) 0.9371(6) 0.0268(11) Uani 1.000000 1 . . .
H8a H 0.30064(19) 0.9072(2) 0.8356(6) 0.0322(13) Uiso 1.000000 1 R . .
H8b H 0.31451(19) 0.9691(2) 0.8949(6) 0.0322(13) Uiso 1.000000 1 R . .
C9 C 0.33236(19) 0.92764(19) 1.1006(6) 0.0242(10) Uani 1.000000 1 . . .
O5 O 0.0 0.0 0.0 0.125(18) Uiso 0.333360 6 S T P


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 C2 1.897(5) . ?
Cu1 Cu1 3.0355(10) 10_567 ?
Cu1 O1 2.004(3) 10_567 ?
Cu1 O1 1.937(3) . ?
Cu1 O2 1.936(3) . ?
Cu1 O3 2.236(3) 15_465 ?
Cu1 N1 1.930(3) . ?
O1 C5 1.340(5) . ?
O2 C9 1.278(5) . ?
O3 C9 1.231(5) . ?
N1 C7 1.292(6) . ?
N1 C8 1.466(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.364(7) . ?
C1 C6 1.418(6) . ?
C2 C3 1.389(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.394(6) . ?
C5 C6 1.422(6) . ?
C6 C7 1.442(6) . ?
C7 H7 0.9300 . ?
C8 H8a 0.9700 . ?
C8 H8b 0.9700 . ?
C8 C9 1.508(6) . ?

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
O2 Cu1 O1 174.89(14) . . ?
O2 Cu1 O1 101.92(13) . 10_567 ?
O3 Cu1 O1 91.70(13) 15_465 . ?
O3 Cu1 O1 92.36(13) 15_465 10_567 ?
O3 Cu1 O2 93.21(14) 15_465 . ?
N1 Cu1 O1 93.27(14) . . ?
N1 Cu1 O1 160.04(14) . 10_567 ?
N1 Cu1 O2 83.99(14) . . ?
N1 Cu1 O3 106.46(14) . 15_465 ?
C5 O1 Cu1 126.0(3) . . ?
C5 O1 Cu1 133.2(3) . 10_567 ?
C9 O2 Cu1 116.6(3) . . ?
C9 O3 Cu1 137.0(3) . 8_664 ?
C7 N1 Cu1 126.8(3) . . ?
C8 N1 Cu1 113.0(3) . . ?
C8 N1 C7 120.1(4) . . ?
C2 C1 H1 119.8(3) . . ?
C6 C1 H1 119.8(3) . . ?
C6 C1 C2 120.4(4) . . ?
C1 C2 Br1 121.5(4) . . ?
C3 C2 Br1 118.1(4) . . ?
C3 C2 C1 120.4(4) . . ?
H3 C3 C2 119.9(3) . . ?
C4 C3 C2 120.1(5) . . ?
C4 C3 H3 119.9(3) . . ?
H4 C4 C3 119.1(3) . . ?
C5 C4 C3 121.7(4) . . ?
C5 C4 H4 119.1(3) . . ?
C4 C5 O1 120.3(4) . . ?
C6 C5 O1 121.8(4) . . ?
C6 C5 C4 117.9(4) . . ?
C5 C6 C1 119.2(4) . . ?
C7 C6 C1 115.8(4) . . ?
C7 C6 C5 125.0(4) . . ?
C6 C7 N1 124.3(4) . . ?
H7 C7 N1 117.8(3) . . ?
H7 C7 C6 117.8(2) . . ?
H8a C8 N1 109.7(2) . . ?
H8b C8 N1 109.7(2) . . ?
H8b C8 H8a 108.2 . . ?
C9 C8 N1 109.8(4) . . ?
C9 C8 H8a 109.7(3) . . ?
C9 C8 H8b 109.7(3) . . ?
O3 C9 O2 123.1(4) . . ?
C8 C9 O2 116.5(4) . . ?
C8 C9 O3 120.3(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
Br1 C2 C1 C6 -177.8(3) . . . . ?
Br1 C2 C3 C4 175.8(4) . . . . ?
Cu1 O1 C5 C4 22.2(4) 10_567 . . . ?
Cu1 O1 C5 C4 -159.8(4) . . . . ?
Cu1 O1 C5 C6 19.9(4) . . . . ?
Cu1 O1 C5 C6 -158.1(4) 10_567 . . . ?
Cu1 O2 C9 O3 178.6(3) . . . . ?
Cu1 O2 C9 C8 -0.4(4) . . . . ?
Cu1 O3 C9 O2 -157.7(5) 8_664 . . . ?
Cu1 O3 C9 C8 21.2(5) 8_664 . . . ?
Cu1 N1 C7 C6 4.2(4) . . . . ?
Cu1 N1 C8 C9 -4.2(3) . . . . ?
O1 C5 C4 C3 -176.1(5) . . . . ?
O1 C5 C6 C1 174.3(4) . . . . ?
O1 C5 C6 C7 -7.0(5) . . . . ?
O2 C9 C8 N1 3.0(4) . . . . ?
O3 C9 C8 N1 -176.0(5) . . . . ?
N1 C7 C6 C1 173.0(5) . . . . ?
N1 C7 C6 C5 -5.8(6) . . . . ?
C1 C2 C3 C4 -3.0(6) . . . . ?
C1 C6 C5 C4 -6.0(5) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
C3 C4 C5 C6 4.1(6) . . . . ?
C4 C5 C6 C7 172.7(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
