# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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 1469547'
_audit_update_record             
;
2016-03-19 deposited with the CCDC.
2016-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6 Cu3 I2 N3 O2, H2 O'
_chemical_formula_sum            'C9 H8 Cu3 I2 N3 O3'
_chemical_formula_weight         650.60

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'
O O 0.0106 0.0060 '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'
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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'


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                   10.7462(3)
_cell_length_b                   10.2236(2)
_cell_length_c                   13.2338(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.619(2)
_cell_angle_gamma                90.00
_cell_volume                     1446.94(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1981
_cell_measurement_theta_min      3.0620
_cell_measurement_theta_max      29.1144

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.987
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    8.643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3007
_exptl_absorpt_correction_T_max  0.3349
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_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  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5314
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2541
_reflns_number_gt                2203
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?


_refine_special_details          
; 
omit -2 50
omit  -2   1   2
omit    -1   1   2
omit     1   1   2
omit     0   2   2
omit     2   0   2
 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)+(0.0289P)²+5.0307P] 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         2541
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0741
_refine_ls_wR_factor_gt          0.0696
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
C1 C -0.0875(5) 0.9907(5) 0.8249(4) 0.0248(12) Uani 1 1 d . . .
C2 C -0.0899(6) 0.9242(7) 0.7352(5) 0.0404(16) Uani 1 1 d . . .
H2 H -0.1606 0.8770 0.7109 0.049 Uiso 1 1 calc R . .
C3 C 0.0136(6) 0.9276(7) 0.6809(5) 0.0417(17) Uani 1 1 d . . .
H3 H 0.0126 0.8812 0.6204 0.050 Uiso 1 1 calc R . .
C4 C 0.1183(5) 0.9990(5) 0.7152(5) 0.0277(13) Uani 1 1 d . . .
C5 C 0.1197(6) 1.0646(6) 0.8067(5) 0.0336(14) Uani 1 1 d . . .
H5 H 0.1901 1.1121 0.8311 0.040 Uiso 1 1 calc R . .
C6 C 0.0170(5) 1.0601(6) 0.8624(5) 0.0315(14) Uani 1 1 d . . .
H6 H 0.0186 1.1035 0.9243 0.038 Uiso 1 1 calc R . .
C7 C -0.2455(5) 1.0913(6) 0.9280(4) 0.0295(13) Uani 1 1 d . . .
H7 H -0.2078 1.1728 0.9379 0.035 Uiso 1 1 calc R . .
C8 C -0.2833(5) 0.8939(6) 0.8790(5) 0.0322(14) Uani 1 1 d . . .
H8 H -0.2766 0.8123 0.8489 0.039 Uiso 1 1 calc R . .
C9 C 0.2280(6) 1.0061(6) 0.6537(5) 0.0321(14) Uani 1 1 d . . .
Cu1 Cu 0.47100(7) 0.66379(7) 0.46409(6) 0.0377(2) Uani 1 1 d . . .
Cu2 Cu 0.36293(9) 0.93039(11) 0.48685(7) 0.0588(3) Uani 1 1 d . . .
Cu3 Cu 0.52392(9) 0.90992(10) 0.36713(10) 0.0699(3) Uani 1 1 d . . .
I1 I 0.42420(4) 1.16016(4) 0.39805(3) 0.03559(13) Uani 1 1 d . . .
I2 I 0.32529(4) 0.77972(4) 0.32161(3) 0.03652(14) Uani 1 1 d . . .
N1 N -0.1972(4) 0.9904(4) 0.8784(3) 0.0244(10) Uani 1 1 d . . .
N2 N -0.3770(4) 0.9314(4) 0.9277(4) 0.0288(11) Uani 1 1 d . . .
N3 N -0.3520(4) 1.0583(4) 0.9599(4) 0.0277(11) Uani 1 1 d . . .
O1 O 0.3132(4) 1.0851(4) 0.6831(4) 0.0407(11) Uani 1 1 d . . .
O2 O 0.2255(4) 0.9335(4) 0.5766(3) 0.0408(11) Uani 1 1 d . . .
O3 O 0.0203(11) 0.7771(10) 0.4421(8) 0.167(4) Uani 1 1 d . . .
H31 H -0.0015 0.8170 0.3869 0.251 Uiso 1 1 d R . .
H32 H 0.0811 0.7874 0.4875 0.251 Uiso 1 1 d R . .

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
C1 0.022(3) 0.026(3) 0.028(3) 0.002(2) 0.013(2) -0.001(2)
C2 0.022(3) 0.055(4) 0.046(4) -0.017(3) 0.012(3) -0.010(3)
C3 0.035(4) 0.055(4) 0.038(4) -0.020(3) 0.019(3) -0.005(3)
C4 0.025(3) 0.024(3) 0.037(3) 0.000(2) 0.017(3) -0.002(2)
C5 0.023(3) 0.038(3) 0.042(4) -0.005(3) 0.011(3) -0.006(3)
C6 0.028(3) 0.038(3) 0.031(3) -0.008(3) 0.010(3) -0.005(3)
C7 0.026(3) 0.027(3) 0.037(3) -0.006(3) 0.013(3) -0.002(3)
C8 0.029(3) 0.029(3) 0.041(4) 0.000(3) 0.015(3) 0.000(3)
C9 0.031(3) 0.025(3) 0.042(4) 0.000(3) 0.016(3) 0.004(3)
Cu1 0.0271(4) 0.0377(4) 0.0518(5) 0.0111(4) 0.0212(4) 0.0058(3)
Cu2 0.0567(6) 0.0771(7) 0.0487(6) -0.0117(5) 0.0355(5) -0.0051(5)
Cu3 0.0375(5) 0.0690(7) 0.1106(9) -0.0191(6) 0.0452(6) -0.0157(5)
I1 0.0360(2) 0.0307(2) 0.0394(2) -0.00001(17) 0.00027(18) -0.00094(18)
I2 0.0416(3) 0.0314(2) 0.0349(2) -0.00164(17) -0.00462(18) -0.00484(18)
N1 0.021(2) 0.026(2) 0.028(2) -0.003(2) 0.013(2) 0.000(2)
N2 0.028(3) 0.025(2) 0.037(3) -0.001(2) 0.016(2) -0.004(2)
N3 0.024(3) 0.025(2) 0.036(3) -0.004(2) 0.013(2) -0.001(2)
O1 0.034(2) 0.037(2) 0.056(3) -0.010(2) 0.026(2) -0.009(2)
O2 0.035(2) 0.047(3) 0.044(3) -0.006(2) 0.022(2) -0.003(2)
O3 0.203(12) 0.168(9) 0.129(8) 0.033(7) 0.004(8) 0.009(9)

_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
C1 C2 1.366(8) . ?
C1 C6 1.380(8) . ?
C1 N1 1.433(7) . ?
C2 C3 1.383(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(8) . ?
C4 C9 1.498(8) . ?
C5 C6 1.386(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N3 1.302(7) . ?
C7 N1 1.353(7) . ?
C7 H7 0.9300 . ?
C8 N2 1.305(7) . ?
C8 N1 1.353(7) . ?
C8 H8 0.9300 . ?
C9 O1 1.253(7) . ?
C9 O2 1.260(7) . ?
Cu1 N2 2.000(5) 4_675 ?
Cu1 N3 2.015(4) 2_546 ?
Cu1 I2 2.6142(9) . ?
Cu1 I1 2.7265(10) 3_676 ?
Cu1 Cu3 2.9060(13) . ?
Cu1 Cu2 2.9895(13) . ?
Cu2 O2 1.984(4) . ?
Cu2 Cu3 2.4666(12) . ?
Cu2 I2 2.6731(10) . ?
Cu2 Cu3 2.7236(15) 3_676 ?
Cu2 I1 2.7358(11) . ?
Cu2 I1 2.7798(12) 3_676 ?
Cu3 O1 1.933(4) 3_676 ?
Cu3 I2 2.5376(10) . ?
Cu3 Cu2 2.7236(15) 3_676 ?
Cu3 I1 2.8191(11) . ?
I1 Cu1 2.7265(10) 3_676 ?
I1 Cu2 2.7798(12) 3_676 ?
N2 N3 1.384(6) . ?
N2 Cu1 2.000(5) 4_476 ?
N3 Cu1 2.015(4) 2_556 ?
O1 Cu3 1.933(4) 3_676 ?
O3 H31 0.8499 . ?
O3 H32 0.8500 . ?

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
C2 C1 C6 120.9(5) . . ?
C2 C1 N1 118.8(5) . . ?
C6 C1 N1 120.3(5) . . ?
C1 C2 C3 119.4(6) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 120.9(6) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 118.8(5) . . ?
C3 C4 C9 120.5(5) . . ?
C5 C4 C9 120.7(5) . . ?
C4 C5 C6 120.6(6) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.3(5) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N3 C7 N1 110.6(5) . . ?
N3 C7 H7 124.7 . . ?
N1 C7 H7 124.7 . . ?
N2 C8 N1 110.5(5) . . ?
N2 C8 H8 124.8 . . ?
N1 C8 H8 124.8 . . ?
O1 C9 O2 126.0(6) . . ?
O1 C9 C4 116.9(5) . . ?
O2 C9 C4 117.1(5) . . ?
N2 Cu1 N3 115.67(18) 4_675 2_546 ?
N2 Cu1 I2 119.50(15) 4_675 . ?
N3 Cu1 I2 103.75(14) 2_546 . ?
N2 Cu1 I1 100.87(15) 4_675 3_676 ?
N3 Cu1 I1 105.07(14) 2_546 3_676 ?
I2 Cu1 I1 111.24(3) . 3_676 ?
N2 Cu1 Cu3 96.61(13) 4_675 . ?
N3 Cu1 Cu3 147.64(13) 2_546 . ?
I2 Cu1 Cu3 54.42(3) . . ?
I1 Cu1 Cu3 68.78(3) 3_676 . ?
N2 Cu1 Cu2 143.34(13) 4_675 . ?
N3 Cu1 Cu2 99.53(13) 2_546 . ?
I2 Cu1 Cu2 56.51(3) . . ?
I1 Cu1 Cu2 57.98(3) 3_676 . ?
Cu3 Cu1 Cu2 49.44(3) . . ?
O2 Cu2 Cu3 174.82(14) . . ?
O2 Cu2 I2 115.91(14) . . ?
Cu3 Cu2 I2 59.01(3) . . ?
O2 Cu2 Cu3 82.68(13) . 3_676 ?
Cu3 Cu2 Cu3 102.37(5) . 3_676 ?
I2 Cu2 Cu3 161.29(4) . 3_676 ?
O2 Cu2 I1 117.91(14) . . ?
Cu3 Cu2 I1 65.38(4) . . ?
I2 Cu2 I1 99.61(3) . . ?
Cu3 Cu2 I1 71.37(4) 3_676 . ?
O2 Cu2 I1 107.35(14) . 3_676 ?
Cu3 Cu2 I1 74.48(4) . 3_676 ?
I2 Cu2 I1 107.87(4) . 3_676 ?
Cu3 Cu2 I1 61.62(3) 3_676 3_676 ?
I1 Cu2 I1 107.55(4) . 3_676 ?
O2 Cu2 Cu1 113.21(14) . . ?
Cu3 Cu2 Cu1 63.52(4) . . ?
I2 Cu2 Cu1 54.64(3) . . ?
Cu3 Cu2 Cu1 117.85(5) 3_676 . ?
I1 Cu2 Cu1 128.86(3) . . ?
I1 Cu2 Cu1 56.26(3) 3_676 . ?
O1 Cu3 Cu2 159.11(16) 3_676 . ?
O1 Cu3 I2 134.54(14) 3_676 . ?
Cu2 Cu3 I2 64.56(3) . . ?
O1 Cu3 Cu2 82.62(14) 3_676 3_676 ?
Cu2 Cu3 Cu2 77.63(5) . 3_676 ?
I2 Cu3 Cu2 142.15(4) . 3_676 ?
O1 Cu3 I1 113.32(13) 3_676 . ?
Cu2 Cu3 I1 61.92(3) . . ?
I2 Cu3 I1 100.82(4) . . ?
Cu2 Cu3 I1 60.17(3) 3_676 . ?
O1 Cu3 Cu1 113.43(14) 3_676 . ?
Cu2 Cu3 Cu1 67.04(4) . . ?
I2 Cu3 Cu1 56.92(3) . . ?
Cu2 Cu3 Cu1 107.39(5) 3_676 . ?
I1 Cu3 Cu1 128.91(4) . . ?
Cu1 I1 Cu2 112.36(3) 3_676 . ?
Cu1 I1 Cu2 65.76(3) 3_676 3_676 ?
Cu2 I1 Cu2 72.45(4) . 3_676 ?
Cu1 I1 Cu3 123.94(3) 3_676 . ?
Cu2 I1 Cu3 52.70(3) . . ?
Cu2 I1 Cu3 58.21(3) 3_676 . ?
Cu3 I2 Cu1 68.66(4) . . ?
Cu3 I2 Cu2 56.43(3) . . ?
Cu1 I2 Cu2 68.85(3) . . ?
C8 N1 C7 105.0(5) . . ?
C8 N1 C1 126.9(5) . . ?
C7 N1 C1 127.7(5) . . ?
C8 N2 N3 106.9(5) . . ?
C8 N2 Cu1 131.6(4) . 4_476 ?
N3 N2 Cu1 121.4(3) . 4_476 ?
C7 N3 N2 107.0(4) . . ?
C7 N3 Cu1 130.1(4) . 2_556 ?
N2 N3 Cu1 122.8(3) . 2_556 ?
C9 O1 Cu3 124.7(4) . 3_676 ?
C9 O2 Cu2 122.4(4) . . ?
H31 O3 H32 132.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H32 O2 0.85 2.38 3.133(12) 147.8 .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.104
_refine_diff_density_min         -1.188
_refine_diff_density_rms         0.133
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1469548'
_audit_update_record             
;
2016-03-19 deposited with the CCDC.
2016-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 Cu2 I N6 O6'
_chemical_formula_sum            'C18 H17 Cu2 I N6 O6'
_chemical_formula_weight         667.38

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   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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                   20.8927(11)
_cell_length_b                   14.2874(6)
_cell_length_c                   7.2925(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.832(6)
_cell_angle_gamma                90.00
_cell_volume                     2060.30(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2140
_cell_measurement_theta_min      3.1309
_cell_measurement_theta_max      29.2005

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1304
_exptl_absorpt_coefficient_mu    3.615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6131
_exptl_absorpt_correction_T_max  0.6709
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_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  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3802
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.40
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1796
_reflns_number_gt                1666
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
omit -2 50
 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)+(0.0398P)²+3.4668P] 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     SHELXL
_refine_ls_extinction_coef       0.0051(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1796
_refine_ls_number_parameters     152
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0716
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.090
_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
C1 C 0.37963(19) 0.3084(2) 0.2776(5) 0.0227(8) Uani 1 1 d . . .
H1 H 0.3799 0.2864 0.3979 0.027 Uiso 1 1 calc R . .
C2 C 0.3707(2) 0.3143(2) -0.0243(5) 0.0240(8) Uani 1 1 d . . .
H2 H 0.3636 0.2973 -0.1525 0.029 Uiso 1 1 calc R . .
C3 C 0.35252(19) 0.1561(2) 0.1000(6) 0.0227(8) Uani 1 1 d . . .
C4 C 0.4021(2) 0.0963(2) 0.2078(6) 0.0291(9) Uani 1 1 d . . .
H4 H 0.4429 0.1195 0.2894 0.035 Uiso 1 1 calc R . .
C5 C 0.3901(2) 0.0010(3) 0.1925(6) 0.0293(9) Uani 1 1 d . . .
H5 H 0.4234 -0.0403 0.2630 0.035 Uiso 1 1 calc R . .
C6 C 0.32898(19) -0.0333(2) 0.0733(5) 0.0228(8) Uani 1 1 d . . .
C7 C 0.2796(2) 0.0283(3) -0.0319(6) 0.0279(8) Uani 1 1 d . . .
H7 H 0.2381 0.0055 -0.1108 0.034 Uiso 1 1 calc R . .
C8 C 0.2917(2) 0.1235(3) -0.0199(6) 0.0281(9) Uani 1 1 d . . .
H8 H 0.2590 0.1650 -0.0924 0.034 Uiso 1 1 calc R . .
C9 C 0.3174(2) -0.1374(3) 0.0610(5) 0.0246(8) Uani 1 1 d . . .
Cu1 Cu 0.42293(3) 0.50187(3) -0.07210(7) 0.02872(18) Uani 1 1 d . . .
I1 I 0.5000 0.40356(2) -0.2500 0.01914(16) Uani 1 2 d S . .
N1 N 0.36613(15) 0.25586(19) 0.1160(4) 0.0214(6) Uani 1 1 d . . .
N2 N 0.38669(16) 0.39839(19) 0.0467(4) 0.0210(7) Uani 1 1 d . . .
N3 N 0.39226(16) 0.39458(19) 0.2409(4) 0.0199(6) Uani 1 1 d . . .
O1 O 0.36565(15) -0.19090(17) 0.1253(4) 0.0325(6) Uani 1 1 d . . .
O2 O 0.25653(16) -0.16459(19) -0.0151(5) 0.0444(8) Uani 1 1 d . . .
H2A H 0.2522 -0.2170 0.0252 0.067 Uiso 0.50 1 calc PR . .
O3 O 0.5033(6) 0.1691(6) 0.5984(17) 0.224(5) Uani 1 1 d U . .
H31 H 0.4785 0.1650 0.6701 0.337 Uiso 1 1 d R . .
H32 H 0.5392 0.1979 0.6619 0.337 Uiso 1 1 d R . .

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
C1 0.033(2) 0.0167(17) 0.0173(18) -0.0005(14) 0.0070(16) -0.0067(16)
C2 0.038(2) 0.0164(17) 0.0189(18) -0.0039(15) 0.0101(16) -0.0083(16)
C3 0.0293(19) 0.0123(16) 0.029(2) -0.0028(15) 0.0123(16) -0.0062(15)
C4 0.0249(19) 0.023(2) 0.033(2) -0.0032(16) -0.0003(18) -0.0052(16)
C5 0.033(2) 0.0192(19) 0.031(2) -0.0009(16) 0.0040(18) 0.0004(16)
C6 0.0287(19) 0.0163(17) 0.026(2) -0.0041(15) 0.0126(16) -0.0041(16)
C7 0.0240(19) 0.0224(19) 0.034(2) -0.0045(17) 0.0042(17) -0.0041(17)
C8 0.028(2) 0.0182(17) 0.033(2) -0.0016(17) 0.0043(18) 0.0021(17)
C9 0.036(2) 0.0159(18) 0.022(2) -0.0024(15) 0.0101(17) -0.0034(17)
Cu1 0.0491(3) 0.0163(3) 0.0205(3) 0.00477(17) 0.0109(2) -0.0008(2)
I1 0.0211(2) 0.0173(2) 0.0168(2) 0.000 0.00313(14) 0.000
N1 0.0285(16) 0.0142(14) 0.0215(16) -0.0051(12) 0.0080(13) -0.0064(13)
N2 0.0278(16) 0.0188(15) 0.0157(15) -0.0018(12) 0.0061(13) -0.0053(13)
N3 0.0258(15) 0.0164(14) 0.0171(15) -0.0014(12) 0.0063(13) -0.0028(12)
O1 0.0418(16) 0.0183(13) 0.0358(16) 0.0003(12) 0.0104(13) -0.0006(13)
O2 0.0424(17) 0.0171(15) 0.061(2) -0.0002(14) -0.0001(16) -0.0097(13)
O3 0.195(8) 0.224(8) 0.240(8) -0.015(7) 0.050(7) 0.010(6)

_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
C1 N3 1.305(4) . ?
C1 N1 1.348(4) . ?
C1 H1 0.9300 . ?
C2 N2 1.309(4) . ?
C2 N1 1.348(5) . ?
C2 H2 0.9300 . ?
C3 C8 1.371(5) . ?
C3 C4 1.377(5) . ?
C3 N1 1.450(4) . ?
C4 C5 1.382(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(6) . ?
C6 C9 1.505(5) . ?
C7 C8 1.381(5) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 O1 1.231(5) . ?
C9 O2 1.272(5) . ?
Cu1 N3 1.974(3) 6_565 ?
Cu1 N2 1.983(3) . ?
Cu1 I1 2.7375(5) 5_665 ?
Cu1 I1 2.7563(5) . ?
Cu1 Cu1 3.0484(11) 5_665 ?
I1 Cu1 2.7375(5) 5_665 ?
I1 Cu1 2.7375(5) 6_565 ?
I1 Cu1 2.7563(5) 2_654 ?
N2 N3 1.384(4) . ?
N3 Cu1 1.974(3) 6_566 ?
O2 H2A 0.8200 . ?
O3 H31 0.8499 . ?
O3 H32 0.8500 . ?

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 C1 N1 110.2(3) . . ?
N3 C1 H1 124.9 . . ?
N1 C1 H1 124.9 . . ?
N2 C2 N1 109.9(3) . . ?
N2 C2 H2 125.1 . . ?
N1 C2 H2 125.1 . . ?
C8 C3 C4 121.6(3) . . ?
C8 C3 N1 120.2(4) . . ?
C4 C3 N1 118.2(3) . . ?
C3 C4 C5 118.8(4) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 120.5(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C7 119.7(3) . . ?
C5 C6 C9 119.1(3) . . ?
C7 C6 C9 121.2(3) . . ?
C8 C7 C6 120.2(4) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C3 C8 C7 119.3(4) . . ?
C3 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
O1 C9 O2 123.9(3) . . ?
O1 C9 C6 119.6(3) . . ?
O2 C9 C6 116.5(3) . . ?
N3 Cu1 N2 140.90(13) 6_565 . ?
N3 Cu1 I1 101.12(9) 6_565 5_665 ?
N2 Cu1 I1 101.23(9) . 5_665 ?
N3 Cu1 I1 99.53(9) 6_565 . ?
N2 Cu1 I1 100.90(9) . . ?
I1 Cu1 I1 112.60(2) 5_665 . ?
N3 Cu1 Cu1 108.83(9) 6_565 5_665 ?
N2 Cu1 Cu1 110.24(10) . 5_665 ?
I1 Cu1 Cu1 56.592(16) 5_665 5_665 ?
I1 Cu1 Cu1 56.004(16) . 5_665 ?
Cu1 I1 Cu1 120.85(2) 5_665 6_565 ?
Cu1 I1 Cu1 83.176(13) 5_665 2_654 ?
Cu1 I1 Cu1 67.40(2) 6_565 2_654 ?
Cu1 I1 Cu1 67.40(2) 5_665 . ?
Cu1 I1 Cu1 83.176(13) 6_565 . ?
Cu1 I1 Cu1 118.72(2) 2_654 . ?
C2 N1 C1 105.8(3) . . ?
C2 N1 C3 127.4(3) . . ?
C1 N1 C3 126.7(3) . . ?
C2 N2 N3 107.2(3) . . ?
C2 N2 Cu1 126.6(2) . . ?
N3 N2 Cu1 124.0(2) . . ?
C1 N3 N2 106.9(3) . . ?
C1 N3 Cu1 127.4(2) . 6_566 ?
N2 N3 Cu1 125.4(2) . 6_566 ?
C9 O2 H2A 109.5 . . ?
H31 O3 H32 107.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A O2 0.82 1.70 2.473(5) 156.3 7_545
O3 H31 O1 0.85 2.30 2.962(11) 134.7 6_556
O3 H32 O1 0.85 2.09 2.844(12) 147.2 5_656

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.889
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.109
