# Electronic Supplementary Material (ESI) for Chemical Science
# This journal is © The Royal Society of Chemistry 2013


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# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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data_1
_database_code_depnum_ccdc_archive 'CCDC 867097'
#TrackingRef '1.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         C7H5N4S1Cu2I1
_chemical_formula_sum            'C7 H5 Cu2 I N4 S'
_chemical_formula_weight         431.19
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'
S S 0.1246 0.1234 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           cubic
_symmetry_space_group_name_H-M   Ia-3d
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+1/4, x+3/4, z+1/4'
'-x, -y+1/2, z'
'y+1/4, -x+1/4, z+3/4'
'x+1/4, -z+1/4, y+3/4'
'x, -y, -z+1/2'
'x+3/4, z+1/4, -y+1/4'
'z+3/4, y+1/4, -x+1/4'
'-x+1/2, y, -z'
'-z+1/4, y+3/4, x+1/4'
'z, x, y'
'y, z, x'
'-y, -z+1/2, x'
'z, -x, -y+1/2'
'-y+1/2, z, -x'
'-z, -x+1/2, y'
'-z+1/2, x, -y'
'y, -z, -x+1/2'
'y+3/4, x+1/4, -z+1/4'
'-y+1/4, -x+1/4, -z+1/4'
'-x+1/4, z+3/4, y+1/4'
'-x+1/4, -z+1/4, -y+1/4'
'z+1/4, -y+1/4, x+3/4'
'-z+1/4, -y+1/4, -x+1/4'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'y+3/4, -x+3/4, z+5/4'
'x+3/4, -z+3/4, y+5/4'
'x+1/2, -y+1/2, -z+1'
'x+5/4, z+3/4, -y+3/4'
'z+5/4, y+3/4, -x+3/4'
'-x+1, y+1/2, -z+1/2'
'-z+3/4, y+5/4, x+3/4'
'z+1/2, x+1/2, y+1/2'
'y+1/2, z+1/2, x+1/2'
'-y+1/2, -z+1, x+1/2'
'z+1/2, -x+1/2, -y+1'
'-y+1, z+1/2, -x+1/2'
'-z+1/2, -x+1, y+1/2'
'-z+1, x+1/2, -y+1/2'
'y+1/2, -z+1/2, -x+1'
'y+5/4, x+3/4, -z+3/4'
'-y+3/4, -x+3/4, -z+3/4'
'-x+3/4, z+5/4, y+3/4'
'-x+3/4, -z+3/4, -y+3/4'
'z+3/4, -y+3/4, x+5/4'
'-z+3/4, -y+3/4, -x+3/4'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-1/4'
'x, y-1/2, -z'
'-y-1/4, x-1/4, -z-3/4'
'-x-1/4, z-1/4, -y-3/4'
'-x, y, z-1/2'
'-x-3/4, -z-1/4, y-1/4'
'-z-3/4, -y-1/4, x-1/4'
'x-1/2, -y, z'
'z-1/4, -y-3/4, -x-1/4'
'-z, -x, -y'
'-y, -z, -x'
'y, z-1/2, -x'
'-z, x, y-1/2'
'y-1/2, -z, x'
'z, x-1/2, -y'
'z-1/2, -x, y'
'-y, z, x-1/2'
'-y-3/4, -x-1/4, z-1/4'
'y-1/4, x-1/4, z-1/4'
'x-1/4, -z-3/4, -y-1/4'
'x-1/4, z-1/4, y-1/4'
'-z-1/4, y-1/4, -x-3/4'
'z-1/4, y-1/4, x-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z+1/4'
'x+1/2, y, -z+1/2'
'-y+1/4, x+1/4, -z-1/4'
'-x+1/4, z+1/4, -y-1/4'
'-x+1/2, y+1/2, z'
'-x-1/4, -z+1/4, y+1/4'
'-z-1/4, -y+1/4, x+1/4'
'x, -y+1/2, z+1/2'
'z+1/4, -y-1/4, -x+1/4'
'-z+1/2, -x+1/2, -y+1/2'
'-y+1/2, -z+1/2, -x+1/2'
'y+1/2, z, -x+1/2'
'-z+1/2, x+1/2, y'
'y, -z+1/2, x+1/2'
'z+1/2, x, -y+1/2'
'z, -x+1/2, y+1/2'
'-y+1/2, z+1/2, x'
'-y-1/4, -x+1/4, z+1/4'
'y+1/4, x+1/4, z+1/4'
'x+1/4, -z-1/4, -y+1/4'
'x+1/4, z+1/4, y+1/4'
'-z+1/4, y+1/4, -x-1/4'
'z+1/4, y+1/4, x+1/4'
_cell_length_a                   41.856(3)
_cell_length_b                   41.856(3)
_cell_length_c                   41.856(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     73329(9)
_cell_formula_units_Z            96
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    38588
_cell_measurement_theta_min      2.2814
_cell_measurement_theta_max      27.4680
_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    0.937
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             19392
_exptl_absorpt_coefficient_mu    2.459
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4041
_exptl_absorpt_correction_T_max  0.4714
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2000)'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      113(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 CCD area-detector'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            201503
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         24.99
_reflns_number_total             5369
_reflns_number_gt                4703
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1689P)^2^+96.6745P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5369
_refine_ls_number_parameters     106
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0864
_refine_ls_wR_factor_ref         0.2795
_refine_ls_wR_factor_gt          0.2627
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.142
_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 0.802052(15) 0.661963(16) 0.016083(15) 0.1208(3) Uani 1 1 d . . .
Cu1 Cu 0.73887(2) 0.73740(2) 0.19622(2) 0.0920(4) Uani 1 1 d . . .
Cu2 Cu 0.73892(3) 0.64831(3) 0.02981(2) 0.1141(4) Uani 1 1 d . . .
S1 S 0.78601(4) 0.68833(4) 0.23944(4) 0.0874(5) Uani 1 1 d . . .
C4 C 0.7452(3) 0.6710(3) 0.0952(2) 0.200(3) Uani 1 1 d D . .
H4 H 0.7589 0.6529 0.0962 0.239 Uiso 1 1 calc R . .
C3 C 0.7418(3) 0.6899(3) 0.1227(3) 0.200(3) Uani 1 1 d D . .
C5 C 0.7107(4) 0.7022(3) 0.0675(3) 0.200(3) Uani 1 1 d D . .
H5 H 0.6982 0.7057 0.0489 0.239 Uiso 1 1 calc R . .
C7 C 0.7217(4) 0.7155(3) 0.1213(3) 0.200(3) Uani 1 1 d D . .
H7 H 0.7174 0.7279 0.1398 0.239 Uiso 1 1 calc R . .
C6 C 0.7080(4) 0.7227(3) 0.0926(3) 0.200(3) Uani 1 1 d D . .
H6 H 0.6966 0.7422 0.0901 0.239 Uiso 1 1 calc R . .
N4 N 0.7306(2) 0.67683(19) 0.06849(17) 0.131(3) Uani 1 1 d D . .
N1 N 0.75885(16) 0.69773(15) 0.18014(15) 0.1004(17) Uani 1 1 d . . .
N3 N 0.7796(3) 0.6564(3) 0.1527(2) 0.189(4) Uani 1 1 d . . .
H3 H 0.7852 0.6438 0.1368 0.227 Uiso 1 1 calc R . .
C2 C 0.7590(3) 0.6814(2) 0.1529(2) 0.133(3) Uani 1 1 d . . .
N2 N 0.7895(3) 0.6561(3) 0.1841(2) 0.189(4) Uani 1 1 d . . .
C1 C 0.7780(2) 0.68047(19) 0.20050(18) 0.102(2) Uani 1 1 d . . .
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
I1 0.1139(5) 0.1374(6) 0.1110(5) 0.0066(3) -0.0274(3) -0.0206(3)
Cu1 0.0970(6) 0.0884(6) 0.0905(6) -0.0051(4) 0.0001(4) 0.0047(4)
Cu2 0.1282(8) 0.1300(8) 0.0842(6) -0.0162(5) -0.0094(5) 0.0181(6)
S1 0.0901(10) 0.0890(10) 0.0830(10) -0.0007(7) -0.0013(7) 0.0025(8)
C4 0.289(7) 0.198(5) 0.111(3) -0.055(3) -0.078(4) 0.138(5)
C3 0.289(7) 0.198(5) 0.111(3) -0.055(3) -0.078(4) 0.138(5)
C5 0.289(7) 0.198(5) 0.111(3) -0.055(3) -0.078(4) 0.138(5)
C7 0.289(7) 0.198(5) 0.111(3) -0.055(3) -0.078(4) 0.138(5)
C6 0.289(7) 0.198(5) 0.111(3) -0.055(3) -0.078(4) 0.138(5)
N4 0.157(6) 0.142(6) 0.094(4) -0.019(4) -0.034(4) 0.047(5)
N1 0.110(4) 0.105(4) 0.086(3) -0.017(3) -0.019(3) 0.021(3)
N3 0.271(9) 0.191(6) 0.104(4) -0.059(4) -0.059(5) 0.129(6)
C2 0.168(9) 0.139(7) 0.092(5) -0.026(5) -0.013(5) 0.064(7)
N2 0.271(9) 0.191(6) 0.104(4) -0.059(4) -0.059(5) 0.129(6)
C1 0.110(5) 0.103(5) 0.093(5) -0.017(4) 0.002(4) 0.021(4)
_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 Cu2 2.6376(12) 9_655 ?
I1 Cu2 2.6971(14) 58_676 ?
I1 Cu2 2.7641(14) . ?
Cu1 N1 1.977(6) . ?
Cu1 S1 2.244(2) 61_566 ?
Cu1 S1 2.252(2) 62_655 ?
Cu2 N4 2.041(7) . ?
Cu2 I1 2.6376(12) 9_655 ?
Cu2 Cu2 2.662(2) 9_655 ?
Cu2 I1 2.6971(14) 80_664 ?
Cu2 Cu2 2.7111(18) 58_676 ?
Cu2 Cu2 2.7111(18) 80_664 ?
S1 C1 1.696(8) . ?
S1 Cu1 2.244(2) 62_655 ?
S1 Cu1 2.252(2) 61_566 ?
C4 N4 1.297(12) . ?
C4 C3 1.403(14) . ?
C4 H4 0.9500 . ?
C3 C7 1.363(15) . ?
C3 C2 1.500(13) . ?
C5 N4 1.349(12) . ?
C5 C6 1.360(14) . ?
C5 H5 0.9500 . ?
C7 C6 1.366(14) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
N1 C2 1.329(10) . ?
N1 C1 1.376(10) . ?
N3 C2 1.355(12) . ?
N3 N2 1.377(10) . ?
N3 H3 0.8800 . ?
N2 C1 1.320(10) . ?
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 I1 Cu2 61.08(4) 9_655 58_676 ?
Cu2 I1 Cu2 59.00(4) 9_655 . ?
Cu2 I1 Cu2 59.51(4) 58_676 . ?
N1 Cu1 S1 122.9(2) . 61_566 ?
N1 Cu1 S1 122.6(2) . 62_655 ?
S1 Cu1 S1 113.21(9) 61_566 62_655 ?
N4 Cu2 I1 109.9(2) . 9_655 ?
N4 Cu2 Cu2 143.4(3) . 9_655 ?
I1 Cu2 Cu2 62.87(4) 9_655 9_655 ?
N4 Cu2 I1 105.1(2) . 80_664 ?
I1 Cu2 I1 113.81(4) 9_655 80_664 ?
Cu2 Cu2 I1 110.52(2) 9_655 80_664 ?
N4 Cu2 Cu2 139.2(2) . 58_676 ?
I1 Cu2 Cu2 110.85(4) 9_655 58_676 ?
Cu2 Cu2 Cu2 60.59(3) 9_655 58_676 ?
I1 Cu2 Cu2 58.38(5) 80_664 58_676 ?
N4 Cu2 Cu2 150.8(3) . 80_664 ?
I1 Cu2 Cu2 60.54(3) 9_655 80_664 ?
Cu2 Cu2 Cu2 60.59(3) 9_655 80_664 ?
I1 Cu2 Cu2 61.47(5) 80_664 80_664 ?
Cu2 Cu2 Cu2 58.81(5) 58_676 80_664 ?
N4 Cu2 I1 101.9(3) . . ?
I1 Cu2 I1 115.17(4) 9_655 . ?
Cu2 Cu2 I1 58.13(4) 9_655 . ?
I1 Cu2 I1 109.84(4) 80_664 . ?
Cu2 Cu2 I1 59.01(4) 58_676 . ?
Cu2 Cu2 I1 107.10(4) 80_664 . ?
C1 S1 Cu1 102.2(3) . 62_655 ?
C1 S1 Cu1 103.8(3) . 61_566 ?
Cu1 S1 Cu1 100.17(8) 62_655 61_566 ?
N4 C4 C3 123.5(10) . . ?
N4 C4 H4 118.3 . . ?
C3 C4 H4 118.3 . . ?
C7 C3 C4 118.1(9) . . ?
C7 C3 C2 121.3(9) . . ?
C4 C3 C2 120.6(9) . . ?
N4 C5 C6 121.7(9) . . ?
N4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C3 C7 C6 118.1(10) . . ?
C3 C7 H7 121.0 . . ?
C6 C7 H7 121.0 . . ?
C5 C6 C7 120.2(10) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C4 N4 C5 117.7(8) . . ?
C4 N4 Cu2 119.5(6) . . ?
C5 N4 Cu2 122.8(6) . . ?
C2 N1 C1 104.9(6) . . ?
C2 N1 Cu1 136.6(6) . . ?
C1 N1 Cu1 118.5(5) . . ?
C2 N3 N2 101.0(7) . . ?
C2 N3 H3 129.5 . . ?
N2 N3 H3 129.5 . . ?
N1 C2 N3 114.0(8) . . ?
N1 C2 C3 126.8(8) . . ?
N3 C2 C3 118.9(8) . . ?
C1 N2 N3 112.4(8) . . ?
N2 C1 N1 107.2(7) . . ?
N2 C1 S1 125.4(7) . . ?
N1 C1 S1 127.5(5) . . ?
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.084
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.138