# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_cuoaecphbr
_database_code_depnum_ccdc_archive 'CCDC 1954202'
loop_
_audit_author_name
_audit_author_address
'Vladislav Komarov'
;Nikolaev Institute of Inorganic Chemistry
Russia
;
_audit_update_record             
;
2019-09-17 deposited with the CCDC.	2019-10-29 downloaded from the CCDC.
;
_audit_creation_date             2019-09-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br8 Cu3, 2(C3 H5 Br N3)'
_chemical_formula_sum            'C6 H10 Br10 Cu3 N6'
_chemical_formula_weight         1155.92
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.9511(3)
_cell_length_b                   12.1653(10)
_cell_length_c                   12.6022(10)
_cell_angle_alpha                67.660(3)
_cell_angle_beta                 89.706(4)
_cell_angle_gamma                86.172(4)
_cell_volume                     558.89(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2261
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.59
_cell_measurement_theta_min      2.96
_shelx_estimated_absorpt_T_max   0.215
_shelx_estimated_absorpt_T_min   0.037
_exptl_absorpt_coefficient_mu    20.708
_exptl_absorpt_correction_T_max  0.4322
_exptl_absorpt_correction_T_min  0.1797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1396 before and 0.0545 after correction. The Ratio of minimum to maximum transmission is 0.4158. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            purple
_exptl_crystal_colour_primary    purple
_exptl_crystal_density_diffrn    3.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             525
_exptl_crystal_size_max          0.467
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.107
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6106
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.640
_diffrn_reflns_theta_min         1.814
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_special_details          ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2523
_reflns_number_total             3146
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.102
_refine_diff_density_min         -1.540
_refine_diff_density_rms         0.346
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         3146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0471P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1049
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C3(H3)
2.b X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Br3A Br 0.37288(12) 1.05116(5) 0.62162(4) 0.00983(12) Uani 1 1 d . . . . .
Br4A Br 0.05819(13) 0.79770(5) 0.64162(4) 0.01133(13) Uani 1 1 d . . . . .
Br2A Br 0.43843(13) 0.65009(5) 0.90876(4) 0.01211(13) Uani 1 1 d . . . . .
Br1A Br 0.78600(13) 0.91683(5) 0.88293(4) 0.01293(13) Uani 1 1 d . . . . .
Br1C Br 0.80719(15) 0.34059(6) 0.57030(5) 0.01910(15) Uani 1 1 d . . . . .
Cu2 Cu 0.0000 1.0000 0.5000 0.0116(2) Uani 1 2 d S T P . .
Cu1 Cu 0.38945(16) 0.85317(6) 0.77786(5) 0.01145(15) Uani 1 1 d . . . . .
N2 N 1.0940(12) 0.3641(5) 0.8645(4) 0.0203(11) Uani 1 1 d . . . . .
H2 H 1.1942 0.3369 0.9327 0.024 Uiso 1 1 calc R . . . .
N1 N 0.9316(13) 0.4742(5) 0.8126(4) 0.0238(12) Uani 1 1 d . . . . .
H1 H 0.9071 0.5292 0.8420 0.029 Uiso 1 1 calc R . . . .
C2 C 0.9027(13) 0.3812(5) 0.6955(4) 0.0123(11) Uani 1 1 d . . . . .
C1 C 1.0772(13) 0.3035(5) 0.7954(4) 0.0131(11) Uani 1 1 d . . . . .
N3 N 1.2228(13) 0.1939(5) 0.8199(4) 0.0237(12) Uani 1 1 d . . . . .
H3A H 1.3383 0.1572 0.8848 0.028 Uiso 1 1 calc R . . . .
H3B H 1.2032 0.1585 0.7712 0.028 Uiso 1 1 calc R . . . .
C3 C 0.8169(15) 0.4845(6) 0.7106(5) 0.0201(13) Uani 1 1 d . . . . .
H3 H 0.6949 0.5527 0.6567 0.024 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
Br3A 0.0126(2) 0.0088(3) 0.0072(2) -0.0020(2) -0.00122(18) -0.00053(19)
Br4A 0.0153(3) 0.0087(3) 0.0083(2) -0.0013(2) -0.00227(18) -0.0010(2)
Br2A 0.0142(3) 0.0093(3) 0.0099(2) -0.0005(2) -0.00123(19) 0.0011(2)
Br1A 0.0150(3) 0.0140(3) 0.0094(2) -0.0040(2) -0.00211(18) -0.0007(2)
Br1C 0.0254(3) 0.0194(3) 0.0136(3) -0.0076(2) -0.0055(2) -0.0003(2)
Cu2 0.0157(4) 0.0089(5) 0.0078(4) -0.0004(4) -0.0037(3) -0.0017(4)
Cu1 0.0148(3) 0.0093(4) 0.0080(3) -0.0008(3) -0.0035(2) -0.0006(3)
N2 0.025(3) 0.026(3) 0.011(2) -0.010(2) -0.0016(19) 0.003(2)
N1 0.035(3) 0.020(3) 0.022(3) -0.016(2) -0.003(2) 0.004(2)
C2 0.012(2) 0.019(3) 0.007(2) -0.005(2) 0.0027(18) -0.004(2)
C1 0.018(3) 0.009(3) 0.010(2) -0.002(2) 0.0019(19) -0.001(2)
N3 0.044(3) 0.016(3) 0.010(2) -0.006(2) -0.003(2) 0.006(2)
C3 0.025(3) 0.021(3) 0.014(3) -0.006(3) 0.001(2) -0.001(3)

_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
Br3A Cu2 2.4037(5) . ?
Br3A Cu1 2.4613(8) . ?
Br4A Cu2 2.4258(5) . ?
Br4A Cu1 2.4775(8) . ?
Br2A Cu1 2.3882(8) . ?
Br1A Cu1 2.4022(8) . ?
Br1C C2 1.871(5) . ?
Cu2 Br3A 2.4037(5) 2_576 ?
Cu2 Br4A 2.4258(5) 2_576 ?
N2 H2 0.8800 . ?
N2 N1 1.363(7) . ?
N2 C1 1.341(7) . ?
N1 H1 0.8800 . ?
N1 C3 1.323(7) . ?
C2 C1 1.404(7) . ?
C2 C3 1.361(8) . ?
C1 N3 1.338(7) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
C3 H3 0.9500 . ?

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
Cu2 Br3A Cu1 94.45(2) . . ?
Cu2 Br4A Cu1 93.49(2) . . ?
Br3A Cu2 Br3A 180.0 . 2_576 ?
Br3A Cu2 Br4A 93.082(18) 2_576 . ?
Br3A Cu2 Br4A 86.917(18) . . ?
Br3A Cu2 Br4A 86.919(18) 2_576 2_576 ?
Br3A Cu2 Br4A 93.082(19) . 2_576 ?
Br4A Cu2 Br4A 180.0 2_576 . ?
Br3A Cu1 Br4A 84.54(3) . . ?
Br2A Cu1 Br3A 171.46(3) . . ?
Br2A Cu1 Br4A 90.34(3) . . ?
Br2A Cu1 Br1A 94.17(3) . . ?
Br1A Cu1 Br3A 89.80(3) . . ?
Br1A Cu1 Br4A 169.54(3) . . ?
N1 N2 H2 125.3 . . ?
C1 N2 H2 125.3 . . ?
C1 N2 N1 109.4(5) . . ?
N2 N1 H1 125.7 . . ?
C3 N1 N2 108.6(5) . . ?
C3 N1 H1 125.7 . . ?
C1 C2 Br1C 123.7(4) . . ?
C3 C2 Br1C 128.9(4) . . ?
C3 C2 C1 107.4(5) . . ?
N2 C1 C2 106.0(5) . . ?
N3 C1 N2 124.0(5) . . ?
N3 C1 C2 129.8(5) . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
N1 C3 C2 108.7(5) . . ?
N1 C3 H3 125.7 . . ?
C2 C3 H3 125.7 . . ?

_shelx_res_file                  
;
    cuoaecphbr.res created by SHELXL-2014/7

TITL cuoaecphbr_pre_a.res in P-1
REM Old TITL CuOaecpHBR_pre in P-1
REM SHELXT solution in P-1
REM R1 0.070, Rweak 0.003, Alpha 0.028, Orientation as input
REM Formula found by SHELXT: C10 N2 Cu3 Br10
CELL 0.71073 3.9511 12.1653 12.6022 67.66 89.706 86.172
ZERR 1 0.0003 0.001 0.001 0.003 0.004 0.004
LATT 1
SFAC C H Br Cu N
UNIT 6 10 10 3 6

L.S. 10
PLAN  20
SIZE 0.107 0.139 0.467
TEMP -123(2)
BOND $H
list 4
fmap 2
acta
OMIT 1 9 0
OMIT 2 13 4
REM <olex2.extras>
REM <HklSrc "%.\\CuOaecpHBr.hkl">
REM </olex2.extras>

WGHT    0.047100
FVAR       0.12119
BR3A  3    0.372876    1.051162    0.621615    11.00000    0.01256    0.00879 =
         0.00717   -0.00196   -0.00122   -0.00053
BR4A  3    0.058193    0.797700    0.641617    11.00000    0.01530    0.00869 =
         0.00831   -0.00128   -0.00227   -0.00098
BR2A  3    0.438432    0.650093    0.908765    11.00000    0.01416    0.00929 =
         0.00986   -0.00053   -0.00123    0.00109
BR1A  3    0.785997    0.916830    0.882931    11.00000    0.01498    0.01402 =
         0.00936   -0.00398   -0.00211   -0.00071
BR1C  3    0.807186    0.340585    0.570303    11.00000    0.02538    0.01942 =
         0.01356   -0.00760   -0.00553   -0.00034
CU2   4    0.000000    1.000000    0.500000    10.50000    0.01571    0.00889 =
         0.00779   -0.00041   -0.00375   -0.00166
CU1   4    0.389454    0.853167    0.777862    11.00000    0.01481    0.00935 =
         0.00798   -0.00080   -0.00355   -0.00061
N2    5    1.093989    0.364059    0.864505    11.00000    0.02515    0.02646 =
         0.01107   -0.00980   -0.00161    0.00253
AFIX  43
H2    2    1.194212    0.336920    0.932682    11.00000   -1.20000
AFIX   0
N1    5    0.931613    0.474154    0.812609    11.00000    0.03523    0.02044 =
         0.02222   -0.01628   -0.00273    0.00412
AFIX  43
H1    2    0.907139    0.529165    0.842037    11.00000   -1.20000
AFIX   0
C2    1    0.902659    0.381224    0.695481    11.00000    0.01173    0.01910 =
         0.00660   -0.00498    0.00270   -0.00415
C1    1    1.077180    0.303514    0.795423    11.00000    0.01836    0.00937 =
         0.00985   -0.00158    0.00189   -0.00128
N3    5    1.222839    0.193904    0.819936    11.00000    0.04417    0.01614 =
         0.01038   -0.00603   -0.00270    0.00627
AFIX  93
H3A   2    1.338270    0.157218    0.884781    11.00000   -1.20000
H3B   2    1.203188    0.158514    0.771209    11.00000   -1.20000
AFIX   0
C3    1    0.816913    0.484483    0.710557    11.00000    0.02492    0.02093 =
         0.01427   -0.00649    0.00123   -0.00140
AFIX  43
H3    2    0.694945    0.552659    0.656734    11.00000   -1.20000
AFIX   0
HKLF 4

REM  cuoaecphbr_pre_a.res in P-1
REM R1 =  0.0394 for    2523 Fo > 4sig(Fo)  and  0.0516 for all    3146 data
REM    115 parameters refined using      0 restraints

END

WGHT      0.0471      0.0000

REM Highest difference peak  1.102,  deepest hole -1.540,  1-sigma level  0.346
Q1    1   0.5747  1.0421  0.6326  11.00000  0.05    1.10
Q2    1   0.3528  0.5982  0.8730  11.00000  0.05    1.09
Q3    1   0.6751  0.6448  0.9213  11.00000  0.05    1.08
Q4    1   1.3992  0.3807  0.8202  11.00000  0.05    1.06
Q5    1   0.9443  0.7609  0.9220  11.00000  0.05    1.05
Q6    1  -0.0191  0.7837  0.5795  11.00000  0.05    1.04
Q7    1   0.2541  0.6575  0.9016  11.00000  0.05    1.04
Q8    1   0.6182  0.3382  0.5771  11.00000  0.05    1.03
Q9    1   0.5403  0.9004  0.6646  11.00000  0.05    1.02
Q10   1   0.0673  0.9625  0.7290  11.00000  0.05    0.99
Q11   1  -0.1612  0.7974  0.6337  11.00000  0.05    0.99
Q12   1   0.5493  0.7040  0.9405  11.00000  0.05    0.97
Q13   1   0.1938  0.8012  0.9191  11.00000  0.05    0.97
Q14   1   0.2203  1.0552  0.3550  11.00000  0.05    0.96
Q15   1   0.6811  0.2771  0.5363  11.00000  0.05    0.96
Q16   1   0.7158  0.2594  0.5831  11.00000  0.05    0.95
Q17   1   0.3182  0.5792  0.8959  11.00000  0.05    0.95
Q18   1   1.0564  0.4224  0.6057  11.00000  0.05    0.94
Q19   1   0.4553  0.5984  0.6445  11.00000  0.05    0.93
Q20   1   0.3879  0.4775  0.5357  11.00000  0.05    0.93
;
_shelx_res_checksum              95469
_olex2_submission_special_instructions 'No special instructions were received'
