# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 Cu2 N12 O0'
_chemical_formula_weight         549.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   19.1704(3)
_cell_length_b                   10.4373(2)
_cell_length_c                   9.36570(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.2850(10)
_cell_angle_gamma                90.00
_cell_volume                     1870.88(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4684
_cell_measurement_theta_min      4.8255
_cell_measurement_theta_max      74.0815

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.951
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    3.169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6653
_exptl_absorpt_correction_T_max  0.7219
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean none
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            7530
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.83
_diffrn_reflns_theta_max         74.24
_reflns_number_total             3721
_reflns_number_gt                3345
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_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 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)+(0.0396P)²+0.9923P] 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         3721
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0286
_refine_ls_wR_factor_ref         0.0772
_refine_ls_wR_factor_gt          0.0747
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
Cu1 Cu -0.938378(13) 0.57824(3) -0.87415(3) 0.00754(9) Uani 1 1 d . . .
Cu2 Cu -0.436257(14) 0.89936(3) -0.37392(3) 0.00867(9) Uani 1 1 d . . .
N9 N -0.46084(8) 0.72220(16) -0.28417(15) 0.0086(3) Uani 1 1 d . . .
N4 N -1.03140(8) 0.24254(16) -0.73388(15) 0.0087(3) Uani 1 1 d . . .
N3 N -1.06751(8) 0.26989(16) -0.85826(15) 0.0094(3) Uani 1 1 d . . .
N1 N -0.99122(8) 0.42276(15) -0.82212(15) 0.0070(3) Uani 1 1 d . . .
N2 N -1.04325(8) 0.37650(16) -0.91051(15) 0.0077(3) Uani 1 1 d . . .
N12 N -0.50487(8) 0.54795(16) -0.18853(16) 0.0082(3) Uani 1 1 d . . .
N11 N -0.45088(8) 0.59348(16) -0.10260(16) 0.0091(3) Uani 1 1 d . . .
N7 N -0.83183(8) 0.59837(16) -0.84163(17) 0.0094(3) Uani 1 1 d . . .
C10 C -0.71012(10) 0.3483(2) -0.26287(19) 0.0111(4) Uani 1 1 d . . .
H10A H -0.6942 0.2931 -0.3318 0.013 Uiso 1 1 calc R . .
N5 N -0.77661(8) 0.39384(16) -0.26214(16) 0.0094(3) Uani 1 1 d . . .
C13 C -0.78581(9) 0.56059(19) -0.74091(18) 0.0093(4) Uani 1 1 d . . .
H13A H -0.7922 0.4911 -0.6808 0.011 Uiso 1 1 calc R . .
C16 C -0.58053(9) 0.73875(19) -0.49087(19) 0.0101(4) Uani 1 1 d . . .
H16A H -0.5571 0.8141 -0.4654 0.012 Uiso 1 1 calc R . .
C3 C -0.91979(9) 0.46927(19) -0.53025(19) 0.0097(4) Uani 1 1 d . . .
H3A H -0.9446 0.5406 -0.5642 0.012 Uiso 1 1 calc R . .
C1 C -0.98483(9) 0.33825(18) -0.71415(18) 0.0070(3) Uani 1 1 d . . .
C15 C -0.63283(9) 0.74073(19) -0.59903(18) 0.0102(4) Uani 1 1 d . . .
H15A H -0.6438 0.8165 -0.6474 0.012 Uiso 1 1 calc R . .
N8 N -0.72762(8) 0.63590(16) -0.73547(16) 0.0089(3) Uani 1 1 d . . .
C4 C -0.86972(10) 0.48266(19) -0.41807(18) 0.0101(4) Uani 1 1 d . . .
H4A H -0.8620 0.5620 -0.3749 0.012 Uiso 1 1 calc R . .
N10 N -0.42465(8) 0.69596(16) -0.16029(16) 0.0104(3) Uani 1 1 d . . .
C20 C -0.50955(9) 0.62954(18) -0.29977(18) 0.0081(3) Uani 1 1 d . . .
C19 C -0.64941(10) 0.51298(19) -0.56995(19) 0.0108(4) Uani 1 1 d . . .
H19A H -0.6717 0.4373 -0.5983 0.013 Uiso 1 1 calc R . .
C7 C -0.89609(9) 0.24293(19) -0.54016(19) 0.0098(4) Uani 1 1 d . . .
H7A H -0.9058 0.1625 -0.5792 0.012 Uiso 1 1 calc R . .
C6 C -0.84461(10) 0.25600(19) -0.42970(19) 0.0108(4) Uani 1 1 d . . .
H6A H -0.8195 0.1850 -0.3959 0.013 Uiso 1 1 calc R . .
C17 C -0.56246(9) 0.6250(2) -0.41956(18) 0.0088(4) Uani 1 1 d . . .
C2 C -0.93310(9) 0.34946(19) -0.59238(18) 0.0077(3) Uani 1 1 d . . .
N6 N -0.67125(8) 0.39252(16) -0.15335(17) 0.0105(3) Uani 1 1 d . . .
C18 C -0.59626(10) 0.51150(19) -0.46224(19) 0.0107(4) Uani 1 1 d . . .
H18A H -0.5832 0.4345 -0.4184 0.013 Uiso 1 1 calc R . .
C12 C -0.73864(10) 0.72898(19) -0.83925(18) 0.0101(4) Uani 1 1 d . . .
H12A H -0.7087 0.7956 -0.8600 0.012 Uiso 1 1 calc R . .
C9 C -0.71471(10) 0.46866(19) -0.07676(19) 0.0112(4) Uani 1 1 d . . .
H9A H -0.7016 0.5108 0.0081 0.013 Uiso 1 1 calc R . .
C5 C -0.83130(9) 0.3763(2) -0.37083(18) 0.0091(4) Uani 1 1 d . . .
C14 C -0.66888(9) 0.6286(2) -0.63484(18) 0.0092(4) Uani 1 1 d . . .
C11 C -0.80198(10) 0.70349(19) -0.90469(18) 0.0104(4) Uani 1 1 d . . .
H11A H -0.8224 0.7498 -0.9809 0.013 Uiso 1 1 calc R . .
C8 C -0.77944(10) 0.47296(19) -0.14366(18) 0.0116(4) Uani 1 1 d . . .
H8A H -0.8178 0.5194 -0.1157 0.014 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
Cu1 N1 1.9884(16) . ?
Cu1 N7 2.0586(16) . ?
Cu1 N2 2.0816(15) 3_363 ?
Cu1 N4 2.0898(16) 2_353 ?
Cu2 N12 2.0240(16) 2_454 ?
Cu2 N6 2.0633(16) 2_454 ?
Cu2 N9 2.0959(16) . ?
Cu2 N11 2.1453(15) 4_575 ?
N9 N10 1.345(2) . ?
N9 C20 1.347(2) . ?
N4 C1 1.345(2) . ?
N4 N3 1.351(2) . ?
N4 Cu1 2.0898(16) 2_343 ?
N3 N2 1.311(2) . ?
N1 C1 1.342(2) . ?
N1 N2 1.349(2) . ?
N2 Cu1 2.0816(15) 3_363 ?
N12 C20 1.345(2) . ?
N12 N11 1.360(2) . ?
N12 Cu2 2.0240(16) 2_444 ?
N11 N10 1.312(2) . ?
N11 Cu2 2.1453(15) 4_576 ?
N7 C13 1.315(2) . ?
N7 C11 1.385(2) . ?
C10 N6 1.316(2) . ?
C10 N5 1.361(2) . ?
C10 H10A 0.9300 . ?
N5 C8 1.387(2) . ?
N5 C5 1.430(2) . ?
C13 N8 1.363(2) . ?
C13 H13A 0.9300 . ?
C16 C15 1.384(3) . ?
C16 C17 1.396(3) . ?
C16 H16A 0.9300 . ?
C3 C4 1.389(3) . ?
C3 C2 1.397(3) . ?
C3 H3A 0.9300 . ?
C1 C2 1.473(2) . ?
C15 C14 1.390(3) . ?
C15 H15A 0.9300 . ?
N8 C12 1.382(2) . ?
N8 C14 1.428(2) . ?
C4 C5 1.390(3) . ?
C4 H4A 0.9300 . ?
C20 C17 1.469(2) . ?
C19 C14 1.392(3) . ?
C19 C18 1.392(3) . ?
C19 H19A 0.9300 . ?
C7 C6 1.395(3) . ?
C7 C2 1.393(3) . ?
C7 H7A 0.9300 . ?
C6 C5 1.389(3) . ?
C6 H6A 0.9300 . ?
C17 C18 1.398(3) . ?
N6 C9 1.382(2) . ?
N6 Cu2 2.0633(16) 2_444 ?
C18 H18A 0.9300 . ?
C12 C11 1.355(3) . ?
C12 H12A 0.9300 . ?
C9 C8 1.358(3) . ?
C9 H9A 0.9300 . ?
C11 H11A 0.9300 . ?
C8 H8A 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
N1 Cu1 N7 124.21(7) . . ?
N1 Cu1 N2 111.25(6) . 3_363 ?
N7 Cu1 N2 103.39(6) . 3_363 ?
N1 Cu1 N4 113.06(6) . 2_353 ?
N7 Cu1 N4 98.33(6) . 2_353 ?
N2 Cu1 N4 104.28(6) 3_363 2_353 ?
N12 Cu2 N6 124.07(7) 2_454 2_454 ?
N12 Cu2 N9 114.72(6) 2_454 . ?
N6 Cu2 N9 99.54(6) 2_454 . ?
N12 Cu2 N11 102.63(6) 2_454 4_575 ?
N6 Cu2 N11 101.38(6) 2_454 4_575 ?
N9 Cu2 N11 114.30(6) . 4_575 ?
N10 N9 C20 105.51(15) . . ?
N10 N9 Cu2 114.12(12) . . ?
C20 N9 Cu2 139.52(12) . . ?
C1 N4 N3 105.35(15) . . ?
C1 N4 Cu1 137.98(12) . 2_343 ?
N3 N4 Cu1 116.64(12) . 2_343 ?
N2 N3 N4 109.02(14) . . ?
C1 N1 N2 105.05(15) . . ?
C1 N1 Cu1 134.05(13) . . ?
N2 N1 Cu1 120.73(12) . . ?
N3 N2 N1 109.89(14) . . ?
N3 N2 Cu1 120.67(12) . 3_363 ?
N1 N2 Cu1 126.27(12) . 3_363 ?
C20 N12 N11 104.59(15) . . ?
C20 N12 Cu2 134.08(13) . 2_444 ?
N11 N12 Cu2 120.99(12) . 2_444 ?
N10 N11 N12 109.76(14) . . ?
N10 N11 Cu2 110.59(11) . 4_576 ?
N12 N11 Cu2 130.88(12) . 4_576 ?
C13 N7 C11 105.48(16) . . ?
C13 N7 Cu1 134.03(13) . . ?
C11 N7 Cu1 116.64(12) . . ?
N6 C10 N5 111.25(17) . . ?
N6 C10 H10A 124.4 . . ?
N5 C10 H10A 124.4 . . ?
C10 N5 C8 106.95(15) . . ?
C10 N5 C5 126.89(16) . . ?
C8 N5 C5 125.80(16) . . ?
N7 C13 N8 111.59(17) . . ?
N7 C13 H13A 124.2 . . ?
N8 C13 H13A 124.2 . . ?
C15 C16 C17 120.83(18) . . ?
C15 C16 H16A 119.6 . . ?
C17 C16 H16A 119.6 . . ?
C4 C3 C2 120.47(18) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
N1 C1 N4 110.69(15) . . ?
N1 C1 C2 124.03(16) . . ?
N4 C1 C2 125.28(16) . . ?
C16 C15 C14 119.55(18) . . ?
C16 C15 H15A 120.2 . . ?
C14 C15 H15A 120.2 . . ?
C13 N8 C12 106.69(15) . . ?
C13 N8 C14 127.32(16) . . ?
C12 N8 C14 125.78(16) . . ?
C3 C4 C5 119.40(18) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
N11 N10 N9 109.29(15) . . ?
N12 C20 N9 110.84(15) . . ?
N12 C20 C17 125.72(17) . . ?
N9 C20 C17 123.36(17) . . ?
C14 C19 C18 119.51(18) . . ?
C14 C19 H19A 120.2 . . ?
C18 C19 H19A 120.2 . . ?
C6 C7 C2 120.46(18) . . ?
C6 C7 H7A 119.8 . . ?
C2 C7 H7A 119.8 . . ?
C5 C6 C7 119.27(18) . . ?
C5 C6 H6A 120.4 . . ?
C7 C6 H6A 120.4 . . ?
C18 C17 C16 119.06(17) . . ?
C18 C17 C20 122.27(18) . . ?
C16 C17 C20 118.66(17) . . ?
C3 C2 C7 119.43(16) . . ?
C3 C2 C1 119.52(17) . . ?
C7 C2 C1 121.03(17) . . ?
C10 N6 C9 105.95(16) . . ?
C10 N6 Cu2 128.72(13) . 2_444 ?
C9 N6 Cu2 122.93(13) . 2_444 ?
C19 C18 C17 120.39(18) . . ?
C19 C18 H18A 119.8 . . ?
C17 C18 H18A 119.8 . . ?
C11 C12 N8 106.09(17) . . ?
C11 C12 H12A 127.0 . . ?
N8 C12 H12A 127.0 . . ?
C8 C9 N6 109.98(16) . . ?
C8 C9 H9A 125.0 . . ?
N6 C9 H9A 125.0 . . ?
C6 C5 C4 120.89(17) . . ?
C6 C5 N5 120.57(17) . . ?
C4 C5 N5 118.52(17) . . ?
C19 C14 C15 120.47(17) . . ?
C19 C14 N8 121.05(17) . . ?
C15 C14 N8 118.44(17) . . ?
C12 C11 N7 110.12(16) . . ?
C12 C11 H11A 124.9 . . ?
N7 C11 H11A 124.9 . . ?
C9 C8 N5 105.84(16) . . ?
C9 C8 H8A 127.1 . . ?
N5 C8 H8A 127.1 . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        74.24
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.086
_database_code_depnum_ccdc_archive 'CCDC 983653'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H7 Cu2 I N6 O0'
_chemical_formula_weight         465.22

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   ' Pbca '

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

_cell_length_a                   13.5477(11)
_cell_length_b                   20.560(2)
_cell_length_c                   8.7151(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2427.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6989
_cell_measurement_theta_min      2.3370
_cell_measurement_theta_max      27.5555

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1759
_exptl_absorpt_coefficient_mu    6.040
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4644
_exptl_absorpt_correction_T_max  0.5834
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_device_type  none
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean none
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            17520
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         27.51
_reflns_number_total             2785
_reflns_number_gt                2525
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0336P)²+0.0000P] 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         2785
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0214
_refine_ls_wR_factor_ref         0.0544
_refine_ls_wR_factor_gt          0.0528
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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 0.471954(11) -0.095200(7) 0.93638(2) 0.02253(7) Uani 1 1 d . . .
Cu1 Cu 0.60657(2) -0.003145(17) 0.90002(4) 0.02744(9) Uani 1 1 d . . .
Cu2 Cu 0.29907(2) -0.091178(13) 0.76711(4) 0.02469(9) Uani 1 1 d . . .
N1 N 0.64309(14) 0.00891(9) 0.6754(2) 0.0197(4) Uani 1 1 d . . .
N2 N 0.72949(14) -0.01608(9) 0.6283(2) 0.0197(4) Uani 1 1 d . . .
N3 N 0.75628(14) 0.01158(9) 0.5004(2) 0.0198(4) Uani 1 1 d . . .
N4 N 0.68715(14) 0.05466(9) 0.4573(2) 0.0199(4) Uani 1 1 d . . .
N5 N 0.29749(15) 0.22195(9) 0.6719(3) 0.0249(5) Uani 1 1 d . . .
N6 N 0.23071(15) 0.31391(10) 0.7502(2) 0.0255(5) Uani 1 1 d . . .
C1 C 0.61826(16) 0.05206(11) 0.5670(3) 0.0175(5) Uani 1 1 d . . .
C2 C 0.52927(17) 0.09300(11) 0.5753(3) 0.0188(5) Uani 1 1 d . . .
C3 C 0.52800(18) 0.15463(12) 0.5101(3) 0.0261(6) Uani 1 1 d . . .
H3A H 0.5804 0.1680 0.4487 0.031 Uiso 1 1 calc R . .
C4 C 0.44969(19) 0.19638(12) 0.5354(3) 0.0270(6) Uani 1 1 d . . .
H4A H 0.4487 0.2373 0.4901 0.032 Uiso 1 1 calc R . .
C5 C 0.37285(17) 0.17657(12) 0.6288(3) 0.0224(5) Uani 1 1 d . . .
C6 C 0.37051(18) 0.11464(12) 0.6881(3) 0.0255(6) Uani 1 1 d . . .
H6A H 0.3168 0.1010 0.7462 0.031 Uiso 1 1 calc R . .
C7 C 0.44858(17) 0.07250(12) 0.6610(3) 0.0226(5) Uani 1 1 d . . .
H7A H 0.4469 0.0305 0.7002 0.027 Uiso 1 1 calc R . .
C8 C 0.30840(18) 0.28682(12) 0.6895(3) 0.0274(6) Uani 1 1 d . . .
H8A H 0.3649 0.3096 0.6615 0.033 Uiso 1 1 calc R . .
C9 C 0.1652(2) 0.26366(13) 0.7719(4) 0.0368(7) Uani 1 1 d . . .
H9A H 0.1023 0.2681 0.8131 0.044 Uiso 1 1 calc R . .
C10 C 0.20506(19) 0.20721(13) 0.7252(4) 0.0371(7) Uani 1 1 d . . .
H10A H 0.1758 0.1663 0.7284 0.044 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 2.6474(4) . ?
I1 Cu1 2.6931(4) 5_657 ?
I1 Cu2 2.7693(4) . ?
Cu1 N1 2.034(2) . ?
Cu1 N3 2.061(2) 2_655 ?
Cu1 I1 2.6931(4) 5_657 ?
Cu1 Cu1 3.3752(7) 5_657 ?
Cu1 Cu2 3.4926(5) 6_657 ?
Cu2 N6 1.998(2) 7_655 ?
Cu2 N2 2.026(2) 6_557 ?
Cu2 N4 2.104(2) 5_656 ?
Cu2 Cu1 3.4926(5) 6_557 ?
N1 C1 1.339(3) . ?
N1 N2 1.343(3) . ?
N2 N3 1.303(3) . ?
N2 Cu2 2.026(2) 6_657 ?
N3 N4 1.343(3) . ?
N3 Cu1 2.061(2) 2_654 ?
N4 C1 1.337(3) . ?
N4 Cu2 2.104(2) 5_656 ?
N5 C8 1.351(3) . ?
N5 C10 1.369(3) . ?
N5 C5 1.433(3) . ?
N6 C8 1.303(3) . ?
N6 C9 1.375(3) . ?
N6 Cu2 1.998(2) 7_665 ?
C1 C2 1.472(3) . ?
C2 C7 1.389(3) . ?
C2 C3 1.389(3) . ?
C3 C4 1.382(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.383(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.375(3) . ?
C6 C7 1.388(3) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 H8A 0.9300 . ?
C9 C10 1.343(4) . ?
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 Cu1 78.390(13) . 5_657 ?
Cu1 I1 Cu2 119.836(12) . . ?
Cu1 I1 Cu2 85.728(11) 5_657 . ?
N1 Cu1 N3 101.51(8) . 2_655 ?
N1 Cu1 I1 111.71(6) . . ?
N3 Cu1 I1 120.67(6) 2_655 . ?
N1 Cu1 I1 120.93(5) . 5_657 ?
N3 Cu1 I1 101.22(6) 2_655 5_657 ?
I1 Cu1 I1 101.610(13) . 5_657 ?
N1 Cu1 Cu1 134.45(6) . 5_657 ?
N3 Cu1 Cu1 123.73(6) 2_655 5_657 ?
I1 Cu1 Cu1 51.407(10) . 5_657 ?
I1 Cu1 Cu1 50.203(10) 5_657 5_657 ?
N1 Cu1 Cu2 58.68(5) . 6_657 ?
N3 Cu1 Cu2 57.33(6) 2_655 6_657 ?
I1 Cu1 Cu2 101.176(14) . 6_657 ?
I1 Cu1 Cu2 154.797(14) 5_657 6_657 ?
Cu1 Cu1 Cu2 150.926(18) 5_657 6_657 ?
N6 Cu2 N2 133.13(8) 7_655 6_557 ?
N6 Cu2 N4 107.33(8) 7_655 5_656 ?
N2 Cu2 N4 100.82(8) 6_557 5_656 ?
N6 Cu2 I1 100.42(6) 7_655 . ?
N2 Cu2 I1 100.17(6) 6_557 . ?
N4 Cu2 I1 115.53(6) 5_656 . ?
N6 Cu2 Cu1 108.94(6) 7_655 6_557 ?
N2 Cu2 Cu1 56.31(6) 6_557 6_557 ?
N4 Cu2 Cu1 59.57(5) 5_656 6_557 ?
I1 Cu2 Cu1 150.360(12) . 6_557 ?
C1 N1 N2 104.86(19) . . ?
C1 N1 Cu1 134.33(16) . . ?
N2 N1 Cu1 117.37(15) . . ?
N3 N2 N1 109.73(18) . . ?
N3 N2 Cu2 126.02(14) . 6_657 ?
N1 N2 Cu2 124.03(15) . 6_657 ?
N2 N3 N4 109.43(18) . . ?
N2 N3 Cu1 125.28(14) . 2_654 ?
N4 N3 Cu1 124.46(15) . 2_654 ?
C1 N4 N3 105.12(19) . . ?
C1 N4 Cu2 137.81(16) . 5_656 ?
N3 N4 Cu2 115.69(15) . 5_656 ?
C8 N5 C10 106.3(2) . . ?
C8 N5 C5 126.5(2) . . ?
C10 N5 C5 126.6(2) . . ?
C8 N6 C9 104.8(2) . . ?
C8 N6 Cu2 127.63(18) . 7_665 ?
C9 N6 Cu2 126.40(17) . 7_665 ?
N4 C1 N1 110.8(2) . . ?
N4 C1 C2 125.7(2) . . ?
N1 C1 C2 123.4(2) . . ?
C7 C2 C3 119.1(2) . . ?
C7 C2 C1 119.8(2) . . ?
C3 C2 C1 120.8(2) . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C3 C4 C5 119.3(2) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 N5 119.2(2) . . ?
C4 C5 N5 119.9(2) . . ?
C5 C6 C7 119.8(2) . . ?
C5 C6 H6A 120.1 . . ?
C7 C6 H6A 120.1 . . ?
C2 C7 C6 120.1(2) . . ?
C2 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
N6 C8 N5 112.3(2) . . ?
N6 C8 H8A 123.8 . . ?
N5 C8 H8A 123.8 . . ?
C10 C9 N6 110.4(2) . . ?
C10 C9 H9A 124.8 . . ?
N6 C9 H9A 124.8 . . ?
C9 C10 N5 106.2(2) . . ?
C9 C10 H10A 126.9 . . ?
N5 C10 H10A 126.9 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.095



_database_code_depnum_ccdc_archive 'CCDC 983654'
