# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1873094'
_audit_update_record             
;
2018-10-13 deposited with the CCDC.
2018-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 Cu2 I6 N6, I2'
_chemical_formula_sum            'C10 H8 Cu2 I8 N6'
_chemical_formula_weight         1354.52

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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   15.105(7)
_cell_length_b                   9.426(2)
_cell_length_c                   17.316(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.93(5)
_cell_angle_gamma                90.00
_cell_volume                     2456.2(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    44323
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      27.92

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    3.662
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2368
_exptl_absorpt_coefficient_mu    11.796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4017
_exptl_absorpt_correction_T_max  0.6851
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.31
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            44323
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         27.92
_reflns_number_total             5869
_reflns_number_gt                4182
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0288P)²+13.7254P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5869
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0803
_refine_ls_wR_factor_gt          0.0693
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.55538(3) 0.06981(5) 0.34148(3) 0.02785(11) Uani 1 1 d . . .
I2 I 0.54031(3) 0.25977(5) 0.11614(3) 0.03331(12) Uani 1 1 d . . .
I3 I 0.51886(3) 0.58542(5) 0.11622(3) 0.03298(12) Uani 1 1 d . . .
I4 I 0.49877(4) 0.88113(6) 0.12599(4) 0.04586(15) Uani 1 1 d . . .
I5 I 0.63123(4) 0.93330(5) 0.57136(3) 0.03579(13) Uani 1 1 d . . .
I6 I 0.77527(3) 0.90646(7) 0.48423(3) 0.04541(15) Uani 1 1 d . . .
I7 I 0.18044(4) 0.28992(7) 0.26143(4) 0.05223(17) Uani 1 1 d . . .
I8 I 0.33085(4) 0.25634(6) 0.18740(3) 0.04683(15) Uani 1 1 d . . .
Cu2 Cu 0.63486(6) 0.24989(8) 0.25547(6) 0.0325(2) Uani 1 1 d . . .
Cu1 Cu 0.67769(8) -0.10928(10) 0.31839(8) 0.0620(4) Uani 1 1 d . . .
N1 N 0.6849(4) 0.6822(6) 0.3022(3) 0.0253(13) Uani 1 1 d . . .
N2 N 0.7516(4) 0.6375(6) 0.2622(4) 0.0265(13) Uani 1 1 d . . .
N3 N 0.7410(4) 0.5011(5) 0.2479(4) 0.0262(13) Uani 1 1 d . . .
N4 N 0.6678(3) 0.4538(5) 0.2789(3) 0.0227(12) Uani 1 1 d . . .
N5 N 0.3206(4) 0.5813(6) 0.4714(3) 0.0251(12) Uani 1 1 d . . .
N6 N 0.1953(5) 0.5287(9) 0.5130(5) 0.059(2) Uani 1 1 d . . .
H6B H 0.1477 0.4833 0.5214 0.071 Uiso 1 1 calc R . .
C1 C 0.6337(4) 0.5683(6) 0.3125(4) 0.0196(13) Uani 1 1 d . . .
C2 C 0.5537(4) 0.5698(6) 0.3535(4) 0.0187(13) Uani 1 1 d . . .
C3 C 0.4828(4) 0.4768(7) 0.3339(4) 0.0246(15) Uani 1 1 d . . .
H3B H 0.4873 0.4113 0.2943 0.030 Uiso 1 1 calc R . .
C4 C 0.4072(4) 0.4806(7) 0.3719(4) 0.0280(16) Uani 1 1 d . . .
H4A H 0.3605 0.4190 0.3578 0.034 Uiso 1 1 calc R . .
C5 C 0.4004(4) 0.5765(6) 0.4314(4) 0.0194(13) Uani 1 1 d . . .
C6 C 0.4688(5) 0.6702(7) 0.4521(4) 0.0265(15) Uani 1 1 d . . .
H6A H 0.4638 0.7351 0.4920 0.032 Uiso 1 1 calc R . .
C7 C 0.5441(4) 0.6659(7) 0.4130(4) 0.0250(15) Uani 1 1 d . . .
H7A H 0.5901 0.7291 0.4268 0.030 Uiso 1 1 calc R . .
C8 C 0.2963(6) 0.6887(10) 0.5165(6) 0.053(3) Uani 1 1 d . . .
H8A H 0.3285 0.7713 0.5278 0.064 Uiso 1 1 calc R . .
C9 C 0.2183(5) 0.6559(10) 0.5419(5) 0.049(2) Uani 1 1 d . . .
H9A H 0.1858 0.7112 0.5738 0.059 Uiso 1 1 calc R . .
C10 C 0.2568(6) 0.4833(10) 0.4698(6) 0.055(3) Uani 1 1 d . . .
H10A H 0.2560 0.3980 0.4428 0.066 Uiso 1 1 calc R . .


_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
I1 Cu1 2.5593(13) . ?
I1 Cu2 2.6169(13) . ?
I2 Cu2 2.6975(18) . ?
I2 I3 3.0865(10) . ?
I3 I4 2.8105(9) . ?
I5 I6 2.7638(15) . ?
I7 I8 2.7214(16) . ?
Cu2 N4 2.018(5) . ?
Cu2 N2 2.061(6) 2_645 ?
Cu1 N1 1.990(5) 1_545 ?
Cu1 N3 2.037(5) 2_645 ?
N1 N2 1.339(7) . ?
N1 C1 1.343(8) . ?
N1 Cu1 1.990(5) 1_565 ?
N2 N3 1.317(7) . ?
N2 Cu2 2.061(6) 2_655 ?
N3 N4 1.347(7) . ?
N3 Cu1 2.037(5) 2_655 ?
N4 C1 1.348(8) . ?
N5 C10 1.333(9) . ?
N5 C8 1.349(10) . ?
N5 C5 1.442(8) . ?
N6 C10 1.313(10) . ?
N6 C9 1.333(11) . ?
N6 H6B 0.8600 . ?
C1 C2 1.453(9) . ?
C2 C7 1.390(9) . ?
C2 C3 1.402(9) . ?
C3 C4 1.367(9) . ?
C3 H3B 0.9300 . ?
C4 C5 1.380(9) . ?
C4 H4A 0.9300 . ?
C5 C6 1.382(9) . ?
C6 C7 1.374(9) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C9 1.329(11) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9300 . ?
C10 H10A 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
Cu1 I1 Cu2 88.06(4) . . ?
Cu2 I2 I3 94.67(2) . . ?
I4 I3 I2 176.56(3) . . ?
N4 Cu2 N2 109.0(2) . 2_645 ?
N4 Cu2 I1 128.35(16) . . ?
N2 Cu2 I1 100.35(15) 2_645 . ?
N4 Cu2 I2 104.44(17) . . ?
N2 Cu2 I2 105.56(18) 2_645 . ?
I1 Cu2 I2 107.33(4) . . ?
N1 Cu1 N3 112.5(2) 1_545 2_645 ?
N1 Cu1 I1 136.25(16) 1_545 . ?
N3 Cu1 I1 103.27(15) 2_645 . ?
N2 N1 C1 106.5(5) . . ?
N2 N1 Cu1 115.8(4) . 1_565 ?
C1 N1 Cu1 137.1(4) . 1_565 ?
N3 N2 N1 108.7(5) . . ?
N3 N2 Cu2 124.2(4) . 2_655 ?
N1 N2 Cu2 126.0(4) . 2_655 ?
N2 N3 N4 109.8(5) . . ?
N2 N3 Cu1 122.4(4) . 2_655 ?
N4 N3 Cu1 127.7(4) . 2_655 ?
N3 N4 C1 105.3(5) . . ?
N3 N4 Cu2 115.6(4) . . ?
C1 N4 Cu2 138.8(4) . . ?
C10 N5 C8 107.5(7) . . ?
C10 N5 C5 127.0(6) . . ?
C8 N5 C5 125.6(6) . . ?
C10 N6 C9 109.4(7) . . ?
C10 N6 H6B 125.3 . . ?
C9 N6 H6B 125.3 . . ?
N1 C1 N4 109.7(5) . . ?
N1 C1 C2 124.7(6) . . ?
N4 C1 C2 125.6(6) . . ?
C7 C2 C3 117.4(6) . . ?
C7 C2 C1 120.8(6) . . ?
C3 C2 C1 121.7(6) . . ?
C4 C3 C2 121.3(6) . . ?
C4 C3 H3B 119.4 . . ?
C2 C3 H3B 119.4 . . ?
C3 C4 C5 119.7(6) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 H4A 120.2 . . ?
C4 C5 C6 120.7(6) . . ?
C4 C5 N5 119.8(6) . . ?
C6 C5 N5 119.5(6) . . ?
C7 C6 C5 119.0(6) . . ?
C7 C6 H6A 120.5 . . ?
C5 C6 H6A 120.5 . . ?
C6 C7 C2 121.9(6) . . ?
C6 C7 H7A 119.1 . . ?
C2 C7 H7A 119.1 . . ?
C9 C8 N5 108.0(7) . . ?
C9 C8 H8A 126.0 . . ?
N5 C8 H8A 126.0 . . ?
C8 C9 N6 107.1(7) . . ?
C8 C9 H9A 126.4 . . ?
N6 C9 H9A 126.4 . . ?
N6 C10 N5 107.9(8) . . ?
N6 C10 H10A 126.0 . . ?
N5 C10 H10A 126.0 . . ?

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
Cu2 I2 I3 I4 -34.6(4) . . . . ?
Cu1 I1 Cu2 N4 -130.8(2) . . . . ?
Cu1 I1 Cu2 N2 -6.28(18) . . . 2_645 ?
Cu1 I1 Cu2 I2 103.76(5) . . . . ?
I3 I2 Cu2 N4 -12.13(16) . . . . ?
I3 I2 Cu2 N2 -127.01(15) . . . 2_645 ?
I3 I2 Cu2 I1 126.59(3) . . . . ?
Cu2 I1 Cu1 N1 -143.0(3) . . . 1_545 ?
Cu2 I1 Cu1 N3 1.54(19) . . . 2_645 ?
C1 N1 N2 N3 0.5(8) . . . . ?
Cu1 N1 N2 N3 -172.1(4) 1_565 . . . ?
C1 N1 N2 Cu2 -168.1(5) . . . 2_655 ?
Cu1 N1 N2 Cu2 19.3(7) 1_565 . . 2_655 ?
N1 N2 N3 N4 -0.6(8) . . . . ?
Cu2 N2 N3 N4 168.3(4) 2_655 . . . ?
N1 N2 N3 Cu1 175.6(4) . . . 2_655 ?
Cu2 N2 N3 Cu1 -15.6(8) 2_655 . . 2_655 ?
N2 N3 N4 C1 0.4(7) . . . . ?
Cu1 N3 N4 C1 -175.5(5) 2_655 . . . ?
N2 N3 N4 Cu2 175.2(4) . . . . ?
Cu1 N3 N4 Cu2 -0.7(7) 2_655 . . . ?
N2 Cu2 N4 N3 28.1(5) 2_645 . . . ?
I1 Cu2 N4 N3 149.0(4) . . . . ?
I2 Cu2 N4 N3 -84.4(5) . . . . ?
N2 Cu2 N4 C1 -159.5(7) 2_645 . . . ?
I1 Cu2 N4 C1 -38.6(8) . . . . ?
I2 Cu2 N4 C1 88.0(7) . . . . ?
N2 N1 C1 N4 -0.3(8) . . . . ?
Cu1 N1 C1 N4 170.0(5) 1_565 . . . ?
N2 N1 C1 C2 179.9(6) . . . . ?
Cu1 N1 C1 C2 -9.8(11) 1_565 . . . ?
N3 N4 C1 N1 0.0(7) . . . . ?
Cu2 N4 C1 N1 -172.9(5) . . . . ?
N3 N4 C1 C2 179.8(6) . . . . ?
Cu2 N4 C1 C2 6.9(11) . . . . ?
N1 C1 C2 C7 -29.1(10) . . . . ?
N4 C1 C2 C7 151.1(7) . . . . ?
N1 C1 C2 C3 149.7(7) . . . . ?
N4 C1 C2 C3 -30.0(10) . . . . ?
C7 C2 C3 C4 0.1(10) . . . . ?
C1 C2 C3 C4 -178.9(6) . . . . ?
C2 C3 C4 C5 -0.8(11) . . . . ?
C3 C4 C5 C6 1.0(10) . . . . ?
C3 C4 C5 N5 179.7(6) . . . . ?
C10 N5 C5 C4 15.4(11) . . . . ?
C8 N5 C5 C4 -163.1(8) . . . . ?
C10 N5 C5 C6 -165.8(8) . . . . ?
C8 N5 C5 C6 15.6(11) . . . . ?
C4 C5 C6 C7 -0.5(10) . . . . ?
N5 C5 C6 C7 -179.2(6) . . . . ?
C5 C6 C7 C2 -0.3(11) . . . . ?
C3 C2 C7 C6 0.5(10) . . . . ?
C1 C2 C7 C6 179.4(6) . . . . ?
C10 N5 C8 C9 0.0(11) . . . . ?
C5 N5 C8 C9 178.8(7) . . . . ?
N5 C8 C9 N6 0.5(12) . . . . ?
C10 N6 C9 C8 -0.7(13) . . . . ?
C9 N6 C10 N5 0.7(12) . . . . ?
C8 N5 C10 N6 -0.4(11) . . . . ?
C5 N5 C10 N6 -179.2(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.92
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.615
_refine_diff_density_min         -2.115
_refine_diff_density_rms         0.223
