# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350

_publ_contact_author_name        'Can-Zhong Lu'
_publ_contact_author_address     
;
State Key Laboratory of Structural Chemistry,
Fujian Institute of Research on the Structure of Matter,
the Chinese Academy of Sciences,
Fuzhou, Fujian 350002,
P. R. China
;

_publ_contact_author_email       czlu@fjirsm.ac.cn
loop_
_publ_author_name
'Zhen-Lan Fang'
'Jian-Gang He'
'Qiang Ju'
'Rong-Ming Yu'
'Jian Zhang'
;
Can-Zhong Lu
;

#=================================END

data_6
_database_code_depnum_ccdc_archive 'CCDC 762256'
#TrackingRef '1-6.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 Cu3 I2 N5'
_chemical_formula_sum            'C12 H8 Cu3 I2 N5'
_chemical_formula_weight         666.68

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'
O O 0.0106 0.0060 '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           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   17.57(2)
_cell_length_b                   15.185(7)
_cell_length_c                   13.384(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.595(6)
_cell_angle_gamma                90.00
_cell_volume                     3136(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3890
_cell_measurement_theta_min      3.1938
_cell_measurement_theta_max      27.4680

_exptl_crystal_description       Prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.1600
_exptl_crystal_size_mid          0.1000
_exptl_crystal_size_min          0.0600
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.829
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2464
_exptl_absorpt_coefficient_mu    7.972
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.400
_exptl_absorpt_correction_T_max  0.620
_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         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Mercury70
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 14.6306
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11883
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3601
_reflns_number_gt                3073
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_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 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^)+(0.0952P)^2^+73.2222P] 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    conster
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3584
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1699
_refine_ls_wR_factor_gt          0.1602
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
Cu4 Cu 0.5000 0.13725(9) 0.2500 0.0293(4) Uani 1 2 d S . .
Cu3 Cu 0.24043(7) 0.25435(7) 0.38250(11) 0.0282(3) Uani 1 1 d . . .
Cu2 Cu 0.21957(8) 0.02820(7) 0.33569(13) 0.0349(3) Uani 1 1 d . . .
Cu1 Cu 0.2500 -0.2500 0.5000 0.0680(7) Uani 1 2 d S . .
I1 I 0.15593(3) 0.13581(3) 0.44024(5) 0.02031(18) Uani 1 1 d . . .
I2 I 0.30674(5) -0.10446(5) 0.51845(7) 0.0502(3) Uani 1 1 d . . .
N3 N 0.4313(4) 0.1383(4) 0.3234(6) 0.0151(13) Uani 1 1 d . . .
C6 C 0.3839(5) 0.0689(5) 0.3238(6) 0.0153(14) Uani 1 1 d . . .
C10 C 0.3554(5) 0.3625(4) 0.2758(7) 0.0165(15) Uani 1 1 d . . .
H13A H 0.2981 0.3443 0.2333 0.020 Uiso 1 1 calc R . .
C12 C 0.3894(5) 0.2083(5) 0.3349(7) 0.0146(14) Uani 1 1 d . . .
C4 C 0.4040(5) -0.0239(5) 0.3160(7) 0.0146(14) Uani 1 1 d . . .
N5 N 0.3542(5) -0.1675(4) 0.2363(7) 0.0213(14) Uani 1 1 d . . .
C5 C 0.3402(5) -0.0803(5) 0.2414(7) 0.0195(16) Uani 1 1 d . . .
H9A H 0.2857 -0.0574 0.1929 0.023 Uiso 1 1 calc R . .
C8 C 0.5214(6) 0.4142(6) 0.4003(9) 0.033(2) Uani 1 1 d . . .
H8A H 0.5781 0.4342 0.4432 0.040 Uiso 1 1 calc R . .
C3 C 0.4876(5) -0.0561(6) 0.3828(7) 0.0210(16) Uani 1 1 d . . .
H7A H 0.5329 -0.0186 0.4282 0.025 Uiso 1 1 calc R . .
C11 C 0.4172(5) 0.3000(5) 0.3387(7) 0.0147(14) Uani 1 1 d . . .
C9 C 0.4563(6) 0.4727(5) 0.3368(8) 0.0274(19) Uani 1 1 d . . .
H4A H 0.4705 0.5319 0.3386 0.033 Uiso 1 1 calc R . .
C2 C 0.5013(6) -0.1460(6) 0.3798(8) 0.0253(18) Uani 1 1 d . . .
H3A H 0.5555 -0.1702 0.4265 0.030 Uiso 1 1 calc R . .
C7 C 0.5031(5) 0.3269(6) 0.4005(8) 0.0270(19) Uani 1 1 d . . .
H2A H 0.5469 0.2864 0.4409 0.032 Uiso 1 1 calc R . .
C1 C 0.4333(6) -0.1989(5) 0.3064(8) 0.0239(17) Uani 1 1 d . . .
H1A H 0.4431 -0.2590 0.3058 0.029 Uiso 1 1 calc R . .
N2 N 0.3162(4) 0.0941(4) 0.3375(6) 0.0173(13) Uani 1 1 d . . .
N4 N 0.3735(4) 0.4486(4) 0.2725(6) 0.0207(14) Uani 1 1 d . . .
N1 N 0.3203(4) 0.1851(4) 0.3450(6) 0.0151(13) 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
Cu4 0.0411(9) 0.0145(7) 0.0556(11) 0.000 0.0420(9) 0.000
Cu3 0.0261(6) 0.0143(5) 0.0529(8) 0.0068(5) 0.0260(5) 0.0056(4)
Cu2 0.0287(6) 0.0198(6) 0.0666(9) -0.0152(5) 0.0311(6) -0.0109(4)
Cu1 0.0728(17) 0.0511(14) 0.0731(18) 0.0047(12) 0.0292(14) -0.0053(12)
I1 0.0263(3) 0.0119(3) 0.0304(3) -0.00332(19) 0.0198(2) -0.00387(18)
I2 0.0538(5) 0.0421(4) 0.0386(4) 0.0054(3) 0.0093(4) -0.0047(3)
N3 0.014(3) 0.012(3) 0.021(3) -0.001(2) 0.010(3) 0.000(2)
C6 0.017(3) 0.011(3) 0.019(4) -0.003(3) 0.009(3) 0.001(3)
C10 0.016(3) 0.006(3) 0.028(4) 0.001(3) 0.010(3) -0.002(3)
C12 0.014(3) 0.012(3) 0.024(4) 0.002(3) 0.013(3) -0.001(3)
C4 0.021(3) 0.008(3) 0.021(4) 0.003(3) 0.014(3) 0.002(3)
N5 0.026(3) 0.008(3) 0.035(4) -0.005(3) 0.019(3) -0.004(3)
C5 0.019(4) 0.014(4) 0.030(4) -0.004(3) 0.015(3) 0.001(3)
C8 0.023(4) 0.026(5) 0.046(6) 0.002(4) 0.012(4) -0.007(4)
C3 0.022(4) 0.021(4) 0.021(4) -0.009(3) 0.012(3) -0.004(3)
C11 0.020(3) 0.005(3) 0.023(4) -0.002(3) 0.014(3) -0.004(3)
C9 0.031(4) 0.011(4) 0.044(5) 0.003(3) 0.021(4) -0.002(3)
C2 0.025(4) 0.025(4) 0.022(4) 0.004(3) 0.009(3) 0.014(3)
C7 0.019(4) 0.021(4) 0.037(5) 0.007(4) 0.010(4) 0.004(3)
C1 0.034(4) 0.012(4) 0.029(4) 0.000(3) 0.017(4) 0.012(3)
N2 0.015(3) 0.010(3) 0.029(4) -0.002(3) 0.012(3) -0.001(2)
N4 0.024(3) 0.007(3) 0.035(4) 0.005(3) 0.018(3) 0.000(2)
N1 0.022(3) 0.004(3) 0.026(3) -0.002(2) 0.016(3) -0.001(2)

_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
Cu4 N3 1.887(7) 2_655 ?
Cu4 N3 1.887(7) . ?
Cu3 N1 2.001(6) . ?
Cu3 N5 2.043(7) 4 ?
Cu3 I1 2.6723(18) . ?
Cu3 I1 2.7553(17) 7_556 ?
Cu3 Cu3 3.002(3) 7_556 ?
Cu2 N2 1.960(7) . ?
Cu2 N4 1.991(7) 4_545 ?
Cu2 I1 2.7161(17) . ?
Cu2 I2 2.9666(19) . ?
Cu1 I2 2.3884(13) 7_546 ?
Cu1 I2 2.3884(13) . ?
I1 Cu3 2.7553(17) 7_556 ?
N3 C12 1.343(9) . ?
N3 C6 1.344(10) . ?
C6 N2 1.343(10) . ?
C6 C4 1.470(10) . ?
C10 N4 1.351(9) . ?
C10 C11 1.383(10) . ?
C10 H13A 0.9300 . ?
C12 N1 1.330(9) . ?
C12 C11 1.470(10) . ?
C4 C5 1.383(11) . ?
C4 C3 1.392(11) . ?
N5 C1 1.339(11) . ?
N5 C5 1.355(10) . ?
N5 Cu3 2.043(7) 4_545 ?
C5 H9A 0.9300 . ?
C8 C7 1.365(13) . ?
C8 C9 1.374(13) . ?
C8 H8A 0.9300 . ?
C3 C2 1.389(12) . ?
C3 H7A 0.9300 . ?
C11 C7 1.391(11) . ?
C9 N4 1.339(11) . ?
C9 H4A 0.9300 . ?
C2 C1 1.383(13) . ?
C2 H3A 0.9300 . ?
C7 H2A 0.9300 . ?
C1 H1A 0.9300 . ?
N2 N1 1.385(9) . ?
N4 Cu2 1.991(7) 4 ?

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
N3 Cu4 N3 179.1(4) 2_655 . ?
N1 Cu3 N5 121.2(3) . 4 ?
N1 Cu3 I1 105.80(18) . . ?
N5 Cu3 I1 105.0(2) 4 . ?
N1 Cu3 I1 106.3(2) . 7_556 ?
N5 Cu3 I1 106.0(2) 4 7_556 ?
I1 Cu3 I1 112.87(7) . 7_556 ?
N1 Cu3 Cu3 120.0(2) . 7_556 ?
N5 Cu3 Cu3 118.9(2) 4 7_556 ?
I1 Cu3 Cu3 57.76(4) . 7_556 ?
I1 Cu3 Cu3 55.11(5) 7_556 7_556 ?
N2 Cu2 N4 136.4(3) . 4_545 ?
N2 Cu2 I1 104.7(2) . . ?
N4 Cu2 I1 110.0(2) 4_545 . ?
N2 Cu2 I2 103.5(2) . . ?
N4 Cu2 I2 96.2(2) 4_545 . ?
I1 Cu2 I2 99.28(7) . . ?
I2 Cu1 I2 180.00(4) 7_546 . ?
Cu3 I1 Cu2 80.42(6) . . ?
Cu3 I1 Cu3 67.13(7) . 7_556 ?
Cu2 I1 Cu3 122.84(8) . 7_556 ?
Cu1 I2 Cu2 121.19(5) . . ?
C12 N3 C6 104.1(6) . . ?
C12 N3 Cu4 126.1(5) . . ?
C6 N3 Cu4 123.3(5) . . ?
N2 C6 N3 111.7(6) . . ?
N2 C6 C4 122.8(7) . . ?
N3 C6 C4 125.4(7) . . ?
N4 C10 C11 123.7(7) . . ?
N4 C10 H13A 118.1 . . ?
C11 C10 H13A 118.1 . . ?
N1 C12 N3 112.3(6) . . ?
N1 C12 C11 123.5(7) . . ?
N3 C12 C11 124.2(6) . . ?
C5 C4 C3 119.2(7) . . ?
C5 C4 C6 120.3(7) . . ?
C3 C4 C6 120.5(7) . . ?
C1 N5 C5 117.8(7) . . ?
C1 N5 Cu3 121.6(6) . 4_545 ?
C5 N5 Cu3 120.5(6) . 4_545 ?
N5 C5 C4 122.5(7) . . ?
N5 C5 H9A 118.8 . . ?
C4 C5 H9A 118.8 . . ?
C7 C8 C9 120.1(8) . . ?
C7 C8 H8A 119.9 . . ?
C9 C8 H8A 119.9 . . ?
C2 C3 C4 118.1(7) . . ?
C2 C3 H7A 121.0 . . ?
C4 C3 H7A 121.0 . . ?
C10 C11 C7 118.2(7) . . ?
C10 C11 C12 118.6(7) . . ?
C7 C11 C12 123.2(7) . . ?
N4 C9 C8 123.2(8) . . ?
N4 C9 H4A 118.4 . . ?
C8 C9 H4A 118.4 . . ?
C1 C2 C3 119.2(8) . . ?
C1 C2 H3A 120.4 . . ?
C3 C2 H3A 120.4 . . ?
C8 C7 C11 118.3(8) . . ?
C8 C7 H2A 120.9 . . ?
C11 C7 H2A 120.9 . . ?
N5 C1 C2 123.0(7) . . ?
N5 C1 H1A 118.5 . . ?
C2 C1 H1A 118.5 . . ?
C6 N2 N1 105.9(6) . . ?
C6 N2 Cu2 132.2(5) . . ?
N1 N2 Cu2 121.7(5) . . ?
C9 N4 C10 116.4(7) . . ?
C9 N4 Cu2 124.3(6) . 4 ?
C10 N4 Cu2 119.1(6) . 4 ?
C12 N1 N2 106.0(6) . . ?
C12 N1 Cu3 132.1(5) . . ?
N2 N1 Cu3 121.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         4.411
_refine_diff_density_min         -2.537
_refine_diff_density_rms         0.304