# 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 2018

####################################################################### 
# 
# 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_130128_Cu26dmPip_4CuBr_block_p5
_database_code_depnum_ccdc_archive 'CCDC 1585395'
_audit_update_record             
;
2017-11-30 deposited with the CCDC.
2018-02-16 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C10 H17 Br2 Cu2.5 N2 S2'
_chemical_formula_moiety         'C10 H17 Br2 Cu2.5 N2 S2'
_chemical_formula_weight         548.05
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.6203(9)
_cell_length_b                   10.1947(13)
_cell_length_c                   11.2268(11)
_cell_angle_alpha                79.856(4)
_cell_angle_beta                 77.927(4)
_cell_angle_gamma                83.881(4)
_cell_volume                     837.35(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2706
_cell_measurement_theta_min      3.90
_cell_measurement_theta_max      27.48
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_exptl_crystal_density_diffrn    2.174
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             531.00
_exptl_absorpt_coefficient_mu    8.178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.028
_exptl_absorpt_correction_T_max  0.038

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            9958
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.531
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3777
_reflns_number_gt                3230
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0191
_refine_ls_wR_factor_ref         0.0454
_refine_ls_wR_factor_gt          0.0448
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3777
_refine_ls_number_parameters     169
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0196P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.002
_refine_diff_density_max         0.58
_refine_diff_density_min         -0.46
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 1.16114(3) 0.34996(2) 0.07993(2) 0.01506(6) Uani 1 1 d . . . . .
Br2 Br 1.04794(3) 0.32541(2) -0.24581(2) 0.01994(6) Uani 1 1 d . . . . .
Cu1 Cu 0.5000 0.5000 0.0000 0.01500(9) Uani 1 2 d S . P . .
Cu2 Cu 0.92416(4) 0.40203(3) -0.05152(2) 0.01961(7) Uani 1 1 d . . . . .
Cu3 Cu 1.30088(4) 0.31559(3) -0.14627(3) 0.02033(7) Uani 1 1 d . . . . .
S1 S 0.66933(7) 0.30562(5) 0.06442(5) 0.01373(11) Uani 1 1 d . . . . .
S2 S 1.50009(7) 0.48601(5) -0.20303(5) 0.01453(11) Uani 1 1 d . . . . .
N1 N 0.6969(2) 0.30247(16) 0.30196(15) 0.0140(4) Uani 1 1 d . . . . .
N2 N 1.4835(3) 0.16167(18) -0.13822(17) 0.0219(4) Uani 1 1 d . . . . .
C1 C 0.6355(3) 0.3657(2) 0.20413(19) 0.0133(4) Uani 1 1 d . . . . .
C2 C 0.6371(3) 0.3533(2) 0.42221(19) 0.0214(5) Uani 1 1 d . . . . .
H2 H 0.6077 0.4517 0.4025 0.026 Uiso 1 1 calc R U . . .
C3 C 0.7882(4) 0.3342(2) 0.4944(2) 0.0300(6) Uani 1 1 d . . . . .
H3A H 0.7401 0.3567 0.5779 0.036 Uiso 1 1 calc R U . . .
H3B H 0.8816 0.3964 0.4527 0.036 Uiso 1 1 calc R U . . .
C4 C 0.8738(4) 0.1910(2) 0.5058(2) 0.0309(6) Uani 1 1 d . . . . .
H4A H 0.9722 0.1823 0.5527 0.037 Uiso 1 1 calc R U . . .
H4B H 0.7828 0.1281 0.5505 0.037 Uiso 1 1 calc R U . . .
C5 C 0.9477(3) 0.1584(2) 0.3771(2) 0.0241(5) Uani 1 1 d . . . . .
H5A H 1.0032 0.0657 0.3840 0.029 Uiso 1 1 calc R U . . .
H5B H 1.0433 0.2188 0.3356 0.029 Uiso 1 1 calc R U . . .
C6 C 0.8055(3) 0.1718(2) 0.29710(19) 0.0168(5) Uani 1 1 d . . . . .
H6 H 0.8711 0.1728 0.2100 0.020 Uiso 1 1 calc R U . . .
C7 C 0.4638(3) 0.2917(2) 0.4935(2) 0.0333(6) Uani 1 1 d . . . . .
H7A H 0.4853 0.1942 0.5097 0.040 Uiso 1 1 calc R U . . .
H7B H 0.3693 0.3154 0.4445 0.040 Uiso 1 1 calc R U . . .
H7C H 0.4257 0.3258 0.5719 0.040 Uiso 1 1 calc R U . . .
C8 C 0.6859(3) 0.0547(2) 0.3283(2) 0.0256(5) Uani 1 1 d . . . . .
H8A H 0.6054 0.0649 0.2692 0.031 Uiso 1 1 calc R U . . .
H8B H 0.6144 0.0531 0.4119 0.031 Uiso 1 1 calc R U . . .
H8C H 0.7613 -0.0291 0.3238 0.031 Uiso 1 1 calc R U . . .
C9 C 1.6137(3) 0.0992(2) -0.1279(2) 0.0224(5) Uani 1 1 d . . . . .
C10 C 1.7823(3) 0.0209(2) -0.1134(2) 0.0332(6) Uani 1 1 d . . . . .
H10A H 1.8841 0.0726 -0.1577 0.040 Uiso 1 1 calc R U . . .
H10B H 1.7879 -0.0622 -0.1471 0.040 Uiso 1 1 calc R U . . .
H10C H 1.7881 -0.0004 -0.0256 0.040 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_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 Cu2 2.5209(4) . ?
Br1 Cu2 2.5238(5) 2_765 ?
Br1 Cu3 2.6093(4) . ?
Br2 Cu3 2.4071(4) . ?
Br2 Cu2 2.4166(4) . ?
Cu1 S2 2.3087(6) 2_765 ?
Cu1 S2 2.3087(6) 1_455 ?
Cu1 S1 2.3356(6) . ?
Cu1 S1 2.3357(6) 2_665 ?
Cu2 S1 2.3087(6) . ?
Cu2 Br1 2.5238(5) 2_765 ?
Cu2 Cu2 2.9205(6) 2_765 ?
Cu2 Cu3 2.9432(5) . ?
Cu3 N2 1.9863(19) . ?
Cu3 S2 2.3445(6) . ?
S1 C1 1.743(2) . ?
S2 C1 1.737(2) 2_765 ?
S2 Cu1 2.3087(6) 1_655 ?
N1 C1 1.320(3) . ?
N1 C6 1.495(2) . ?
N1 C2 1.496(2) . ?
N2 C9 1.136(3) . ?
C1 S2 1.737(2) 2_765 ?
C2 C3 1.519(3) . ?
C2 C7 1.529(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.530(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.519(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.527(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C8 1.526(3) . ?
C6 H6 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.462(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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 Br1 Cu2 70.752(12) . 2_765 ?
Cu2 Br1 Cu3 69.994(12) . . ?
Cu2 Br1 Cu3 101.331(12) 2_765 . ?
Cu3 Br2 Cu2 75.200(13) . . ?
S2 Cu1 S2 180.00(3) 2_765 1_455 ?
S2 Cu1 S1 76.896(19) 2_765 . ?
S2 Cu1 S1 103.104(19) 1_455 . ?
S2 Cu1 S1 103.104(19) 2_765 2_665 ?
S2 Cu1 S1 76.896(19) 1_455 2_665 ?
S1 Cu1 S1 180.0 . 2_665 ?
S1 Cu2 Br2 116.610(18) . . ?
S1 Cu2 Br1 106.249(18) . . ?
Br2 Cu2 Br1 107.545(14) . . ?
S1 Cu2 Br1 104.975(18) . 2_765 ?
Br2 Cu2 Br1 111.931(14) . 2_765 ?
Br1 Cu2 Br1 109.248(12) . 2_765 ?
S1 Cu2 Cu2 117.70(2) . 2_765 ?
Br2 Cu2 Cu2 125.658(17) . 2_765 ?
Br1 Cu2 Cu2 54.670(11) . 2_765 ?
Br1 Cu2 Cu2 54.578(12) 2_765 2_765 ?
S1 Cu2 Cu3 137.576(19) . . ?
Br2 Cu2 Cu3 52.254(9) . . ?
Br1 Cu2 Cu3 56.413(11) . . ?
Br1 Cu2 Cu3 117.164(13) 2_765 . ?
Cu2 Cu2 Cu3 85.240(14) 2_765 . ?
N2 Cu3 S2 97.65(6) . . ?
N2 Cu3 Br2 123.73(5) . . ?
S2 Cu3 Br2 120.118(19) . . ?
N2 Cu3 Br1 107.40(6) . . ?
S2 Cu3 Br1 100.174(17) . . ?
Br2 Cu3 Br1 105.067(14) . . ?
N2 Cu3 Cu2 143.45(6) . . ?
S2 Cu3 Cu2 115.281(19) . . ?
Br2 Cu3 Cu2 52.547(11) . . ?
Br1 Cu3 Cu2 53.593(9) . . ?
C1 S1 Cu2 104.42(7) . . ?
C1 S1 Cu1 84.95(7) . . ?
Cu2 S1 Cu1 88.55(2) . . ?
C1 S2 Cu1 85.91(7) 2_765 1_655 ?
C1 S2 Cu3 105.37(7) 2_765 . ?
Cu1 S2 Cu3 92.35(2) 1_655 . ?
C1 N1 C6 120.33(17) . . ?
C1 N1 C2 119.34(17) . . ?
C6 N1 C2 119.86(16) . . ?
C9 N2 Cu3 161.57(18) . . ?
N1 C1 S2 123.63(16) . 2_765 ?
N1 C1 S1 124.11(16) . . ?
S2 C1 S1 112.16(11) 2_765 . ?
N1 C2 C3 111.09(19) . . ?
N1 C2 C7 110.18(18) . . ?
C3 C2 C7 114.09(19) . . ?
N1 C2 H2 107.0 . . ?
C3 C2 H2 107.0 . . ?
C7 C2 H2 107.0 . . ?
C2 C3 C4 112.12(19) . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 108.54(18) . . ?
C5 C4 H4A 110.0 . . ?
C3 C4 H4A 110.0 . . ?
C5 C4 H4B 110.0 . . ?
C3 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
C4 C5 C6 113.6(2) . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
N1 C6 C8 111.65(18) . . ?
N1 C6 C5 110.45(16) . . ?
C8 C6 C5 113.35(18) . . ?
N1 C6 H6 107.0 . . ?
C8 C6 H6 107.0 . . ?
C5 C6 H6 107.0 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C10 178.8(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
C6 N1 C1 S2 177.00(14) . . . 2_765 ?
C2 N1 C1 S2 4.9(3) . . . 2_765 ?
C6 N1 C1 S1 1.0(3) . . . . ?
C2 N1 C1 S1 -171.04(15) . . . . ?
Cu2 S1 C1 N1 -93.69(17) . . . . ?
Cu1 S1 C1 N1 179.11(17) . . . . ?
Cu2 S1 C1 S2 89.93(10) . . . 2_765 ?
Cu1 S1 C1 S2 2.74(9) . . . 2_765 ?
C1 N1 C2 C3 -144.39(19) . . . . ?
C6 N1 C2 C3 43.5(3) . . . . ?
C1 N1 C2 C7 88.2(2) . . . . ?
C6 N1 C2 C7 -83.9(2) . . . . ?
N1 C2 C3 C4 -50.9(3) . . . . ?
C7 C2 C3 C4 74.4(3) . . . . ?
C2 C3 C4 C5 59.2(3) . . . . ?
C3 C4 C5 C6 -58.5(3) . . . . ?
C1 N1 C6 C8 -86.8(2) . . . . ?
C2 N1 C6 C8 85.2(2) . . . . ?
C1 N1 C6 C5 146.08(19) . . . . ?
C2 N1 C6 C5 -41.9(2) . . . . ?
C4 C5 C6 N1 48.9(2) . . . . ?
C4 C5 C6 C8 -77.3(2) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2014-1


