# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_p21c
_database_code_depnum_ccdc_archive 'CCDC 1956280'
loop_
_audit_author_name
_audit_author_address
'Yan Sui'
;Jinggangshan University
China
;
_audit_update_record             
;
2019-09-27 deposited with the CCDC.	2019-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H26 Br6 Cu N2'
_chemical_formula_sum            'C10 H26 Br6 Cu N2'
_chemical_formula_weight         717.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.9377(3)
_cell_length_b                   9.3838(2)
_cell_length_c                   19.0539(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.192(2)
_cell_angle_gamma                90
_cell_volume                     2134.42(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5368
_cell_measurement_theta_min      4.0100
_cell_measurement_theta_max      28.0760

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.232
_exptl_crystal_F_000             1356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    12.247
_shelx_estimated_absorpt_T_min   0.073
_shelx_estimated_absorpt_T_max   0.183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.13563
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;    
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, EosS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12439
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.413
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3974
_reflns_number_gt                2884
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  ?

_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)+(0.0333P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3974
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0763
_refine_ls_wR_factor_gt          0.0704
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_restrained_S_all      0.955
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.75168(5) 0.57331(6) 0.53291(3) 0.04489(17) Uani 1 1 d . . . . .
Br2 Br 0.76977(5) 0.86607(5) 0.71390(3) 0.04430(17) Uani 1 1 d . . . . .
Br3 Br 1.00003(5) 0.73090(5) 0.60951(3) 0.03650(15) Uani 1 1 d . . . . .
Br4 Br 0.73762(5) 0.48547(6) 0.71801(3) 0.04299(17) Uani 1 1 d . . . . .
Br5 Br 0.51342(6) 0.76038(7) 0.40980(3) 0.0600(2) Uani 1 1 d . . . . .
Br6 Br 0.28764(6) 0.96205(7) 0.47693(3) 0.0553(2) Uani 1 1 d . . . . .
C1 C 0.1990(5) 0.8349(6) 0.4175(3) 0.0458(15) Uani 1 1 d . . . . .
H1A H 0.2230 0.8422 0.3691 0.055 Uiso 1 1 calc R U . . .
H1B H 0.2079 0.7369 0.4328 0.055 Uiso 1 1 calc R U . . .
C2 C 0.0793(5) 0.8804(5) 0.4244(3) 0.0372(14) Uani 1 1 d . . . . .
H2A H 0.0744 0.9817 0.4148 0.045 Uiso 1 1 calc R U . . .
H2B H 0.0559 0.8655 0.4726 0.045 Uiso 1 1 calc R U . . .
C3 C -0.1164(5) 0.8608(6) 0.3898(4) 0.0606(19) Uani 1 1 d . . . . .
H3A H -0.1687 0.8163 0.3583 0.091 Uiso 1 1 calc R U . . .
H3B H -0.1167 0.9619 0.3822 0.091 Uiso 1 1 calc R U . . .
H3C H -0.1375 0.8409 0.4374 0.091 Uiso 1 1 calc R U . . .
C4 C -0.0029(5) 0.6467(5) 0.3919(3) 0.0536(18) Uani 1 1 d . . . . .
H4A H -0.0610 0.6021 0.3647 0.080 Uiso 1 1 calc R U . . .
H4B H -0.0171 0.6320 0.4409 0.080 Uiso 1 1 calc R U . . .
H4C H 0.0681 0.6057 0.3798 0.080 Uiso 1 1 calc R U . . .
C5 C 0.0283(6) 0.8271(6) 0.3012(3) 0.0569(18) Uani 1 1 d . . . . .
H5A H 0.0984 0.7816 0.2912 0.085 Uiso 1 1 calc R U . . .
H5B H 0.0344 0.9275 0.2924 0.085 Uiso 1 1 calc R U . . .
H5C H -0.0292 0.7873 0.2718 0.085 Uiso 1 1 calc R U . . .
C6 C 0.5949(5) 0.6034(5) 0.3672(3) 0.0446(15) Uani 1 1 d . . . . .
H6A H 0.5945 0.6132 0.3165 0.053 Uiso 1 1 calc R U . . .
H6B H 0.6721 0.6035 0.3832 0.053 Uiso 1 1 calc R U . . .
C7 C 0.5388(4) 0.4675(5) 0.3879(3) 0.0357(13) Uani 1 1 d . . . . .
H7A H 0.4593 0.4750 0.3779 0.043 Uiso 1 1 calc R U . . .
H7B H 0.5476 0.4541 0.4381 0.043 Uiso 1 1 calc R U . . .
C8 C 0.5616(5) 0.3452(6) 0.2733(3) 0.0447(15) Uani 1 1 d . . . . .
H8A H 0.5874 0.2595 0.2511 0.067 Uiso 1 1 calc R U . . .
H8B H 0.5997 0.4257 0.2535 0.067 Uiso 1 1 calc R U . . .
H8C H 0.4824 0.3551 0.2659 0.067 Uiso 1 1 calc R U . . .
C9 C 0.7090(5) 0.3237(6) 0.3613(3) 0.0482(16) Uani 1 1 d . . . . .
H9A H 0.7350 0.2371 0.3400 0.072 Uiso 1 1 calc R U . . .
H9B H 0.7249 0.3215 0.4107 0.072 Uiso 1 1 calc R U . . .
H9C H 0.7465 0.4036 0.3404 0.072 Uiso 1 1 calc R U . . .
C10 C 0.5279(5) 0.2091(6) 0.3796(3) 0.0572(18) Uani 1 1 d . . . . .
H10A H 0.4488 0.2163 0.3712 0.086 Uiso 1 1 calc R U . . .
H10B H 0.5417 0.2037 0.4292 0.086 Uiso 1 1 calc R U . . .
H10C H 0.5564 0.1249 0.3572 0.086 Uiso 1 1 calc R U . . .
Cu1 Cu 0.81383(5) 0.66599(6) 0.64173(3) 0.02981(17) Uani 1 1 d . . . . .
N1 N -0.0011(4) 0.8033(4) 0.3765(2) 0.0322(11) Uani 1 1 d . . . . .
N2 N 0.5855(4) 0.3377(4) 0.3502(2) 0.0322(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Cu1 2.3655(8) . ?
Br2 Cu1 2.3869(8) . ?
Br3 Cu1 2.3870(8) . ?
Br4 Cu1 2.4121(8) . ?
Br5 C6 1.944(5) . ?
Br6 C1 1.953(5) . ?
C1 C2 1.499(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N1 1.507(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.500(7) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 N1 1.499(6) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 N1 1.494(6) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.494(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N2 1.521(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N2 1.493(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 N2 1.496(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N2 1.499(7) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
C2 C1 Br6 106.9(3) . . ?
C2 C1 H1A 110.3 . . ?
Br6 C1 H1A 110.3 . . ?
C2 C1 H1B 110.3 . . ?
Br6 C1 H1B 110.3 . . ?
H1A C1 H1B 108.6 . . ?
C1 C2 N1 114.6(4) . . ?
C1 C2 H2A 108.6 . . ?
N1 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
N1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 Br5 108.1(4) . . ?
C7 C6 H6A 110.1 . . ?
Br5 C6 H6A 110.1 . . ?
C7 C6 H6B 110.1 . . ?
Br5 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
C6 C7 N2 113.2(4) . . ?
C6 C7 H7A 108.9 . . ?
N2 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
N2 C7 H7B 108.9 . . ?
H7A C7 H7B 107.8 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Br1 Cu1 Br2 136.48(4) . . ?
Br1 Cu1 Br3 99.09(3) . . ?
Br2 Cu1 Br3 98.89(3) . . ?
Br1 Cu1 Br4 98.75(3) . . ?
Br2 Cu1 Br4 96.95(3) . . ?
Br3 Cu1 Br4 133.44(3) . . ?
C5 N1 C4 109.7(4) . . ?
C5 N1 C3 109.1(5) . . ?
C4 N1 C3 107.8(4) . . ?
C5 N1 C2 111.0(4) . . ?
C4 N1 C2 111.2(4) . . ?
C3 N1 C2 107.9(4) . . ?
C8 N2 C9 109.2(4) . . ?
C8 N2 C10 108.6(4) . . ?
C9 N2 C10 109.2(4) . . ?
C8 N2 C7 111.0(4) . . ?
C9 N2 C7 111.4(4) . . ?
C10 N2 C7 107.4(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
Br6 C1 C2 N1 174.2(3) . . . . ?
Br5 C6 C7 N2 172.4(3) . . . . ?
C1 C2 N1 C5 -60.5(6) . . . . ?
C1 C2 N1 C4 61.9(6) . . . . ?
C1 C2 N1 C3 180.0(5) . . . . ?
C6 C7 N2 C8 -65.5(6) . . . . ?
C6 C7 N2 C9 56.4(6) . . . . ?
C6 C7 N2 C10 176.0(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
C1 H1B Br1 0.97 3.02 3.988(5) 174.4 3_666
C2 H2A Br3 0.97 2.88 3.823(5) 165.4 3_676
C2 H2B Br3 0.97 2.98 3.915(5) 163.0 1_455
C3 H3C Br6 0.96 3.05 3.664(6) 122.9 3_576
C4 H4C Br4 0.96 3.10 4.000(6) 156.5 3_666
C5 H5B Br2 0.96 3.04 3.767(6) 133.8 3_676
C5 H5C Br2 0.96 3.01 3.942(6) 165.6 4_475
C5 H5C Br3 0.96 3.12 3.707(5) 121.2 4_475
C6 H6A Br2 0.97 2.88 3.607(5) 133.0 4_575
C6 H6B Br1 0.97 3.02 3.676(6) 126.5 .
C7 H7A Br1 0.97 3.08 3.806(5) 133.1 3_666
C7 H7A Br4 0.97 3.00 3.888(5) 153.4 3_666
C8 H8A Br4 0.96 2.98 3.894(5) 158.8 4_565
C8 H8B Br2 0.96 2.92 3.849(6) 163.6 4_575
C8 H8C Br4 0.96 3.04 3.914(6) 152.1 3_666
C9 H9A Br4 0.96 3.13 4.000(6) 152.2 4_565
C10 H10B Br6 0.96 3.12 3.855(6) 134.4 3_666

_refine_diff_density_max         0.679
_refine_diff_density_min         -1.014
_refine_diff_density_rms         0.154

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_p21c_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1956281'
loop_
_audit_author_name
_audit_author_address
'Yan Sui'
;Jinggangshan University
China
;
_audit_update_record             
;
2019-09-27 deposited with the CCDC.	2019-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H26 Br6 Cu N2'
_chemical_formula_sum            'C10 H26 Br6 Cu N2'
_chemical_formula_weight         717.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.9733(16)
_cell_length_b                   9.414(2)
_cell_length_c                   19.243(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.089(13)
_cell_angle_gamma                90
_cell_volume                     2168.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    363.00(10)
_cell_measurement_reflns_used    930
_cell_measurement_theta_min      3.9680
_cell_measurement_theta_max      20.2570

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.197
_exptl_crystal_F_000             1356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    12.052
_shelx_estimated_absorpt_T_min   0.074
_shelx_estimated_absorpt_T_max   0.186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.07173
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      363.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, EosS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6979
_diffrn_reflns_av_unetI/netI     0.2153
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.403
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             3943
_reflns_number_gt                1556
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0167P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00032(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3943
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2230
_refine_ls_R_factor_gt           0.0798
_refine_ls_wR_factor_ref         0.1458
_refine_ls_wR_factor_gt          0.1082
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_restrained_S_all      0.923
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.24737(13) 0.0747(2) 0.03451(8) 0.0674(6) Uani 1 1 d . . . . .
Br2 Br 0.23189(14) 0.3655(2) 0.21366(8) 0.0706(6) Uani 1 1 d . . . . .
Br3 Br 0.00080(11) 0.2312(2) 0.11049(8) 0.0584(6) Uani 1 1 d . . . . .
Br4 Br 0.26242(13) -0.0130(2) 0.21803(8) 0.0651(6) Uani 1 1 d . . . . .
Br5 Br 0.48555(17) 0.2400(3) 0.40891(9) 0.0932(8) Uani 1 1 d . . . . .
Br6 Br 0.71712(15) 0.0420(2) 0.47717(10) 0.0869(8) Uani 1 1 d . . . . .
C1 C 0.8020(13) 0.1669(18) 0.4186(9) 0.079(6) Uani 1 1 d . . . . .
H1A H 0.7756 0.1606 0.3710 0.095 Uiso 1 1 calc R U . . .
H1B H 0.7938 0.2644 0.4341 0.095 Uiso 1 1 calc R U . . .
C2 C 0.9225(13) 0.1225(18) 0.4227(7) 0.060(5) Uani 1 1 d . . . . .
H2A H 0.9474 0.1343 0.4703 0.072 Uiso 1 1 calc R U . . .
H2B H 0.9268 0.0220 0.4119 0.072 Uiso 1 1 calc R U . . .
C3 C 1.1153(11) 0.140(2) 0.3901(9) 0.089(7) Uani 1 1 d . . . . .
H3A H 1.1686 0.1828 0.3594 0.134 Uiso 1 1 calc R U . . .
H3B H 1.1139 0.0391 0.3825 0.134 Uiso 1 1 calc R U . . .
H3C H 1.1360 0.1590 0.4374 0.134 Uiso 1 1 calc R U . . .
C4 C 1.0053(14) 0.353(2) 0.3917(9) 0.085(6) Uani 1 1 d . . . . .
H4A H 1.0656 0.3964 0.3668 0.127 Uiso 1 1 calc R U . . .
H4B H 1.0160 0.3664 0.4407 0.127 Uiso 1 1 calc R U . . .
H4C H 0.9359 0.3953 0.3778 0.127 Uiso 1 1 calc R U . . .
C5 C 0.9727(12) 0.181(2) 0.3030(7) 0.090(7) Uani 1 1 d . . . . .
H5A H 0.9071 0.2351 0.2925 0.134 Uiso 1 1 calc R U . . .
H5B H 0.9582 0.0818 0.2942 0.134 Uiso 1 1 calc R U . . .
H5C H 1.0333 0.2119 0.2742 0.134 Uiso 1 1 calc R U . . .
C6 C 0.4060(15) 0.394(2) 0.3654(9) 0.092(7) Uani 1 1 d . . . . .
H6A H 0.4095 0.3851 0.3152 0.110 Uiso 1 1 calc R U . . .
H6B H 0.3282 0.3929 0.3793 0.110 Uiso 1 1 calc R U . . .
C7 C 0.4590(12) 0.528(2) 0.3875(7) 0.080(8) Uani 1 1 d . . . . .
H7A H 0.5387 0.5210 0.3792 0.096 Uiso 1 1 calc R U . . .
H7B H 0.4482 0.5388 0.4372 0.096 Uiso 1 1 calc R U . . .
C8 C 0.4384(12) 0.6574(17) 0.2754(7) 0.068(5) Uani 1 1 d . . . . .
H8A H 0.4069 0.7400 0.2537 0.102 Uiso 1 1 calc R U . . .
H8B H 0.4061 0.5735 0.2553 0.102 Uiso 1 1 calc R U . . .
H8C H 0.5177 0.6565 0.2683 0.102 Uiso 1 1 calc R U . . .
C9 C 0.2887(11) 0.6757(19) 0.3635(8) 0.074(6) Uani 1 1 d . . . . .
H9A H 0.2739 0.6695 0.4124 0.111 Uiso 1 1 calc R U . . .
H9B H 0.2497 0.6011 0.3397 0.111 Uiso 1 1 calc R U . . .
H9C H 0.2637 0.7661 0.3464 0.111 Uiso 1 1 calc R U . . .
C10 C 0.4706(14) 0.7903(19) 0.3809(9) 0.087(7) Uani 1 1 d . . . . .
H10A H 0.5497 0.7843 0.3734 0.130 Uiso 1 1 calc R U . . .
H10B H 0.4559 0.7953 0.4299 0.130 Uiso 1 1 calc R U . . .
H10C H 0.4419 0.8739 0.3586 0.130 Uiso 1 1 calc R U . . .
Cu1 Cu 0.18635(13) 0.1666(2) 0.14232(9) 0.0479(6) Uani 1 1 d . . . . .
N1 N 1.0026(10) 0.2000(16) 0.3762(6) 0.051(4) Uani 1 1 d . . . . .
N2 N 0.4144(10) 0.6606(17) 0.3509(6) 0.055(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Cu1 2.364(2) . ?
Br2 Cu1 2.385(3) . ?
Br3 Cu1 2.383(2) . ?
Br4 Cu1 2.409(3) . ?
Br5 C6 1.927(19) . ?
Br6 C1 1.921(14) . ?
C1 C2 1.504(18) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N1 1.502(17) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.486(16) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 N1 1.469(19) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 N1 1.464(16) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.47(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N2 1.53(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N2 1.481(15) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 N2 1.532(14) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N2 1.509(18) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
C2 C1 Br6 107.9(11) . . ?
C2 C1 H1A 110.1 . . ?
Br6 C1 H1A 110.1 . . ?
C2 C1 H1B 110.1 . . ?
Br6 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
N1 C2 C1 116.6(13) . . ?
N1 C2 H2A 108.1 . . ?
C1 C2 H2A 108.1 . . ?
N1 C2 H2B 108.1 . . ?
C1 C2 H2B 108.1 . . ?
H2A C2 H2B 107.3 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 Br5 107.8(12) . . ?
C7 C6 H6A 110.2 . . ?
Br5 C6 H6A 110.2 . . ?
C7 C6 H6B 110.2 . . ?
Br5 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
C6 C7 N2 114.5(13) . . ?
C6 C7 H7A 108.6 . . ?
N2 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
N2 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Br1 Cu1 Br3 99.04(9) . . ?
Br1 Cu1 Br2 136.19(10) . . ?
Br3 Cu1 Br2 99.18(9) . . ?
Br1 Cu1 Br4 99.02(9) . . ?
Br3 Cu1 Br4 133.33(9) . . ?
Br2 Cu1 Br4 96.72(9) . . ?
C5 N1 C4 108.9(14) . . ?
C5 N1 C3 110.3(12) . . ?
C4 N1 C3 108.5(14) . . ?
C5 N1 C2 110.9(12) . . ?
C4 N1 C2 111.6(13) . . ?
C3 N1 C2 106.7(13) . . ?
C8 N2 C10 107.8(13) . . ?
C8 N2 C7 111.5(12) . . ?
C10 N2 C7 109.2(13) . . ?
C8 N2 C9 110.5(11) . . ?
C10 N2 C9 107.5(13) . . ?
C7 N2 C9 110.1(12) . . ?

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
C3 H3C Br6 0.96 3.06 3.670(17) 122.8 3_756
C4 H4C Br4 0.96 3.13 4.039(17) 159.4 2_655
C5 H5C Br2 0.96 3.02 3.954(15) 165.1 1_655
C5 H5B Br2 0.96 3.06 3.860(17) 142.0 2_645
C5 H5A Br4 0.96 3.13 4.051(18) 161.9 2_655
C2 H2A Br3 0.97 3.05 3.978(14) 161.5 4_666
C2 H2B Br3 0.97 2.90 3.850(17) 165.3 2_645
C1 H1B Br1 0.97 3.02 3.987(18) 172.7 2_655
C8 H8C Br4 0.96 3.09 3.927(15) 146.7 2_655
C8 H8B Br2 0.96 2.97 3.881(15) 158.9 .
C8 H8A Br4 0.96 2.98 3.909(15) 163.9 1_565
C7 H7A Br1 0.97 3.09 3.846(15) 135.6 2_655
C7 H7A Br4 0.97 3.05 3.927(14) 151.4 2_655
C6 H6A Br2 0.97 2.89 3.595(18) 130.2 .
C6 H6A Br2 0.97 2.89 3.595(18) 130.2 .
C7 H7A Br4 0.97 3.05 3.927(14) 151.4 2_655
C7 H7A Br1 0.97 3.09 3.846(15) 135.6 2_655
C8 H8A Br4 0.96 2.98 3.909(15) 163.9 1_565
C8 H8B Br2 0.96 2.97 3.881(15) 158.9 .
C8 H8C Br4 0.96 3.09 3.927(15) 146.7 2_655
C10 H10B Br6 0.96 3.14 3.875(16) 134.9 3_666
C1 H1B Br1 0.97 3.02 3.987(18) 172.7 2_655
C2 H2B Br3 0.97 2.90 3.850(17) 165.3 2_645
C2 H2A Br3 0.97 3.05 3.978(14) 161.5 4_666
C5 H5A Br4 0.96 3.13 4.051(18) 161.9 2_655
C5 H5B Br2 0.96 3.06 3.860(17) 142.0 2_645
C5 H5C Br2 0.96 3.02 3.954(15) 165.1 1_655
C4 H4C Br4 0.96 3.13 4.039(17) 159.4 2_655
C3 H3C Br6 0.96 3.06 3.670(17) 122.8 3_756

_refine_diff_density_max         0.980
_refine_diff_density_min         -0.738
_refine_diff_density_rms         0.175

_shelxl_version_number           2014-3

