# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_C:\compound
_database_code_depnum_ccdc_archive 'CCDC 1583360'
_audit_update_record             
;
2017-10-31 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H7 Cu3 N8'
_chemical_formula_weight         429.86

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.978(3)
_cell_length_b                   8.800(3)
_cell_length_c                   10.660(4)
_cell_angle_alpha                112.999(3)
_cell_angle_beta                 97.436(4)
_cell_angle_gamma                106.403(4)
_cell_volume                     636.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2133
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      28.02

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.244
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    4.973
_shelx_estimated_absorpt_T_min   0.369
_shelx_estimated_absorpt_T_max   0.436
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4878
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.701
_diffrn_reflns_theta_max         28.381
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2814
_reflns_number_gt                2303
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0453P)²+0.4891P] 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         2814
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0906
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
Cu1 Cu 0.37200(6) 0.16914(6) 0.39614(5) 0.03063(14) Uani 1 1 d . . . . .
Cu2 Cu 0.51711(6) -0.04347(6) 0.24270(5) 0.02926(14) Uani 1 1 d . . . . .
Cu3 Cu 0.33452(7) 0.30226(6) 0.01400(5) 0.03071(14) Uani 1 1 d . . . . .
N1 N 0.0944(4) 0.0588(4) 0.3317(3) 0.0269(7) Uani 1 1 d . . . . .
N2 N 0.0141(4) -0.0815(4) 0.2042(3) 0.0284(7) Uani 1 1 d . . . . .
N3 N -0.1610(4) -0.1152(4) 0.1762(3) 0.0246(6) Uani 1 1 d . . . . .
N4 N -0.2016(4) 0.0000(4) 0.2830(3) 0.0227(6) Uani 1 1 d . . . . .
N5 N 0.0509(4) 0.5509(4) 0.7649(3) 0.0269(7) Uani 1 1 d . . . . .
N6 N 0.4095(5) 0.1758(4) 0.1105(3) 0.0349(8) Uani 1 1 d . . . . .
N7 N 0.4124(5) 0.6941(4) 0.1545(4) 0.0344(7) Uani 1 1 d . . . . .
N8 N 0.4724(5) 0.0312(4) 0.4679(4) 0.0371(8) Uani 1 1 d . . . . .
C1 C -0.0400(5) 0.1060(4) 0.3783(4) 0.0225(7) Uani 1 1 d . . . . .
C2 C -0.0124(5) 0.2567(4) 0.5147(4) 0.0216(7) Uani 1 1 d . . . . .
C3 C 0.1459(5) 0.3242(5) 0.6237(4) 0.0258(8) Uani 1 1 d . . . . .
H3 H 0.2314 0.2701 0.6130 0.031 Uiso 1 1 calc R U . . .
C4 C 0.1734(5) 0.4718(5) 0.7471(4) 0.0308(8) Uani 1 1 d . . . . .
H4 H 0.2789 0.5177 0.8196 0.037 Uiso 1 1 calc R U . . .
C5 C -0.1043(5) 0.4845(5) 0.6627(4) 0.0285(8) Uani 1 1 d . . . . .
H5 H -0.1902 0.5376 0.6778 0.034 Uiso 1 1 calc R U . . .
C6 C -0.1378(5) 0.3399(5) 0.5366(4) 0.0268(8) Uani 1 1 d . . . . .
H6 H -0.2443 0.2974 0.4658 0.032 Uiso 1 1 calc R U . . .
C7 C 0.0889(6) 0.7135(5) 0.8984(4) 0.0437(11) Uani 1 1 d . . . . .
H7A H 0.0978 0.6856 0.9769 0.066 Uiso 1 1 calc R U . . .
H7B H -0.0079 0.7573 0.8929 0.066 Uiso 1 1 calc R U . . .
H7C H 0.2011 0.8025 0.9113 0.066 Uiso 1 1 calc R U . . .
C8 C 0.4436(5) 0.1053(5) 0.1734(4) 0.0273(8) Uani 1 1 d . . . . .
C9 C 0.3717(5) 0.5501(5) 0.1037(4) 0.0287(8) Uani 1 1 d . . . . .
C10 C 0.4699(5) 0.4249(4) 0.4769(4) 0.0236(7) 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
Cu1 C10 1.933(3) . ?
Cu1 N8 1.954(3) . ?
Cu1 N1 2.047(3) . ?
Cu1 C8 2.401(4) . ?
Cu1 Cu2 2.6150(9) . ?
Cu2 C8 1.918(4) . ?
Cu2 N7 1.981(3) 1_545 ?
Cu2 N4 2.122(3) 1_655 ?
Cu2 N8 2.334(4) . ?
Cu3 C9 1.921(4) . ?
Cu3 N6 1.940(3) . ?
Cu3 N3 2.029(3) 2 ?
N1 C1 1.341(4) . ?
N1 N2 1.341(4) . ?
N2 N3 1.311(4) . ?
N3 N4 1.344(4) . ?
N3 Cu3 2.029(3) 2 ?
N4 C1 1.344(4) . ?
N4 Cu2 2.122(3) 1_455 ?
N5 C4 1.343(5) . ?
N5 C5 1.344(5) . ?
N5 C7 1.489(5) . ?
N6 C8 1.133(5) . ?
N7 C9 1.091(5) . ?
N7 Cu2 1.981(3) 1_565 ?
N8 N8 1.147(6) 2_656 ?
C1 C2 1.471(5) . ?
C2 C6 1.390(5) . ?
C2 C3 1.398(5) . ?
C3 C4 1.376(5) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 C6 1.370(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C10 C10 1.136(7) 2_666 ?

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
C10 Cu1 N8 124.17(15) . . ?
C10 Cu1 N1 114.44(13) . . ?
N8 Cu1 N1 110.58(14) . . ?
C10 Cu1 C8 98.03(14) . . ?
N8 Cu1 C8 103.86(14) . . ?
N1 Cu1 C8 101.30(12) . . ?
C10 Cu1 Cu2 125.49(11) . . ?
N8 Cu1 Cu2 59.35(11) . . ?
N1 Cu1 Cu2 111.53(9) . . ?
C8 Cu1 Cu2 44.71(9) . . ?
C8 Cu2 N7 126.29(15) . 1_545 ?
C8 Cu2 N4 115.64(14) . 1_655 ?
N7 Cu2 N4 100.40(12) 1_545 1_655 ?
C8 Cu2 N8 107.58(14) . . ?
N7 Cu2 N8 101.62(13) 1_545 . ?
N4 Cu2 N8 102.16(12) 1_655 . ?
C8 Cu2 Cu1 61.73(12) . . ?
N7 Cu2 Cu1 125.48(10) 1_545 . ?
N4 Cu2 Cu1 125.33(8) 1_655 . ?
N8 Cu2 Cu1 46.07(8) . . ?
C9 Cu3 N6 124.57(15) . . ?
C9 Cu3 N3 127.23(14) . 2 ?
N6 Cu3 N3 106.48(13) . 2 ?
C1 N1 N2 105.7(3) . . ?
C1 N1 Cu1 135.1(2) . . ?
N2 N1 Cu1 118.5(2) . . ?
N3 N2 N1 108.4(3) . . ?
N2 N3 N4 110.9(3) . . ?
N2 N3 Cu3 122.1(2) . 2 ?
N4 N3 Cu3 126.7(2) . 2 ?
C1 N4 N3 104.0(3) . . ?
C1 N4 Cu2 143.1(2) . 1_455 ?
N3 N4 Cu2 112.9(2) . 1_455 ?
C4 N5 C5 120.3(3) . . ?
C4 N5 C7 119.5(3) . . ?
C5 N5 C7 120.2(3) . . ?
C8 N6 Cu3 174.2(3) . . ?
C9 N7 Cu2 172.7(3) . 1_565 ?
N8 N8 Cu1 168.1(5) 2_656 . ?
N8 N8 Cu2 117.1(4) 2_656 . ?
Cu1 N8 Cu2 74.58(11) . . ?
N1 C1 N4 111.0(3) . . ?
N1 C1 C2 124.1(3) . . ?
N4 C1 C2 124.9(3) . . ?
C6 C2 C3 118.4(3) . . ?
C6 C2 C1 121.3(3) . . ?
C3 C2 C1 120.2(3) . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
N5 C4 C3 121.3(3) . . ?
N5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
N5 C5 C6 121.0(3) . . ?
N5 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C2 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C2 C6 H6 120.1 . . ?
N5 C7 H7A 109.5 . . ?
N5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N6 C8 Cu2 166.9(4) . . ?
N6 C8 Cu1 119.5(3) . . ?
Cu2 C8 Cu1 73.55(13) . . ?
N7 C9 Cu3 172.0(4) . . ?
C10 C10 Cu1 178.6(5) 2_666 . ?

_refine_diff_density_max         0.683
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.105

_shelxl_version_number           2014-3

