# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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 1049827'
_audit_update_record             
;
2015-02-16 deposited with the CCDC.
2015-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C10 H8 Cu3 I2 N4 O5), H2O'
_chemical_formula_sum            'C20 H18 Cu6 I4 N8 O11'
_chemical_formula_weight         1435.32

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           orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   7.6681(8)
_cell_length_b                   31.909(3)
_cell_length_c                   15.4268(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3774.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.526
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2672.0
_exptl_absorpt_coefficient_mu    6.650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3497
_exptl_absorpt_correction_T_max  0.5560
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            21363
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         27.94
_reflns_number_total             4540
_reflns_number_gt                3414
_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)+(0.0437P)²+26.7612P] 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       0.00006(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4540
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_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 0.08571(11) 0.06192(3) 0.32611(6) 0.0351(2) Uani 1 1 d . . .
Cu2 Cu 0.07830(11) 0.03422(3) 0.02995(6) 0.0361(2) Uani 1 1 d . . .
Cu3 Cu 0.24911(10) 0.22911(2) -0.12667(6) 0.0352(2) Uani 1 1 d . . .
I1 I 0.26207(6) 0.023765(14) 0.45058(3) 0.03621(14) Uani 1 1 d . . .
I2 I 0.25545(6) 0.047867(16) 0.17888(3) 0.03815(14) Uani 1 1 d . . .
C1 C 0.4834(9) 0.1695(2) -0.0704(5) 0.0398(17) Uani 1 1 d . . .
C2 C 0.3055(8) 0.1486(2) -0.0645(4) 0.0309(14) Uani 1 1 d . . .
C3 C 0.2803(8) 0.1081(2) -0.0351(5) 0.0336(15) Uani 1 1 d . . .
H3A H 0.3758 0.0924 -0.0170 0.040 Uiso 1 1 calc R . .
C4 C -0.0121(9) 0.1142(2) -0.0608(5) 0.0359(16) Uani 1 1 d . . .
H4A H -0.1237 0.1028 -0.0612 0.043 Uiso 1 1 calc R . .
C5 C 0.0125(9) 0.1550(2) -0.0898(5) 0.0412(18) Uani 1 1 d . . .
H5A H -0.0830 0.1706 -0.1084 0.049 Uiso 1 1 calc R . .
C6 C 0.4867(9) 0.2057(2) 0.3609(6) 0.0441(19) Uani 1 1 d . . .
C7 C 0.3107(8) 0.1851(2) 0.3599(5) 0.0328(15) Uani 1 1 d . . .
C8 C 0.2862(9) 0.1420(2) 0.3503(5) 0.0361(16) Uani 1 1 d . . .
H8A H 0.3825 0.1244 0.3454 0.043 Uiso 1 1 calc R . .
C9 C -0.0091(8) 0.15240(19) 0.3581(5) 0.0315(14) Uani 1 1 d . . .
H9A H -0.1219 0.1416 0.3584 0.038 Uiso 1 1 calc R . .
C10 C 0.0139(9) 0.19504(19) 0.3679(5) 0.0354(16) Uani 1 1 d . . .
H10A H -0.0827 0.2124 0.3744 0.043 Uiso 1 1 calc R . .
N1 N 0.1209(7) 0.09112(17) -0.0323(4) 0.0331(12) Uani 1 1 d . . .
N2 N 0.1712(7) 0.17226(16) -0.0912(4) 0.0318(12) Uani 1 1 d . . .
N3 N 0.1261(7) 0.12576(16) 0.3481(4) 0.0302(12) Uani 1 1 d . . .
N4 N 0.1743(7) 0.21159(16) 0.3681(4) 0.0333(13) Uani 1 1 d . . .
O1 O 0.4789(6) 0.20715(14) -0.1007(4) 0.0442(13) Uani 1 1 d . . .
O1W O 0.2551(7) 0.2187(2) -0.2691(4) 0.0589(16) Uani 1 1 d . . .
H1WA H 0.2536 0.1926 -0.2796 0.071 Uiso 1 1 d R . .
H1WB H 0.3489 0.2289 -0.2897 0.071 Uiso 1 1 d R . .
O2 O 0.6122(7) 0.15115(18) -0.0454(5) 0.0602(17) Uani 1 1 d . . .
O7 O 0.6189(7) 0.18490(18) 0.3555(6) 0.073(2) Uani 1 1 d . . .
O8 O 0.4834(6) 0.24600(14) 0.3659(4) 0.0427(13) Uani 1 1 d . . .
O2W O 0.5000 0.1052(10) -0.2500 0.347(18) Uiso 1 2 d S . .
H2WA H 0.5684 0.0844 -0.2542 0.416 Uiso 1 1 d 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 N3 2.089(5) . ?
Cu1 I1 2.6454(10) . ?
Cu1 I2 2.6554(10) 3 ?
Cu1 I2 2.6559(10) . ?
Cu1 Cu1 2.6911(18) 3 ?
Cu1 Cu2 2.7007(13) 3 ?
Cu2 N1 2.080(5) . ?
Cu2 I1 2.6284(10) 7 ?
Cu2 I1 2.6483(10) 3 ?
Cu2 Cu2 2.6581(17) 5 ?
Cu2 Cu1 2.7007(13) 3 ?
Cu2 I2 2.7043(10) . ?
Cu3 O1 1.938(5) . ?
Cu3 O8 1.955(5) 2_554 ?
Cu3 N4 1.983(5) 2_554 ?
Cu3 N2 1.987(5) . ?
Cu3 O1W 2.222(6) . ?
I1 Cu2 2.6284(10) 7_556 ?
I1 Cu2 2.6483(10) 3 ?
I2 Cu1 2.6554(10) 3 ?
C1 O2 1.212(8) . ?
C1 O1 1.289(8) . ?
C1 C2 1.522(9) . ?
C2 N2 1.343(8) . ?
C2 C3 1.381(9) . ?
C3 N1 1.338(8) . ?
C3 H3A 0.9300 . ?
C4 N1 1.332(8) . ?
C4 C5 1.391(9) . ?
C4 H4A 0.9300 . ?
C5 N2 1.335(8) . ?
C5 H5A 0.9300 . ?
C6 O7 1.215(8) . ?
C6 O8 1.288(8) . ?
C6 C7 1.501(9) . ?
C7 N4 1.350(8) . ?
C7 C8 1.398(9) . ?
C8 N3 1.333(8) . ?
C8 H8A 0.9300 . ?
C9 N3 1.350(8) . ?
C9 C10 1.380(9) . ?
C9 H9A 0.9300 . ?
C10 N4 1.339(8) . ?
C10 H10A 0.9300 . ?
N4 Cu3 1.983(5) 2 ?
O1W H1WA 0.8504 . ?
O1W H1WB 0.8499 . ?
O8 Cu3 1.955(5) 2 ?
O2W H2WA 0.8497 . ?

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 Cu1 I1 104.76(16) . . ?
N3 Cu1 I2 108.40(15) . 3 ?
I1 Cu1 I2 116.55(3) . 3 ?
N3 Cu1 I2 103.36(16) . . ?
I1 Cu1 I2 107.01(3) . . ?
I2 Cu1 I2 115.44(3) 3 . ?
N3 Cu1 Cu1 102.39(15) . 3 ?
I1 Cu1 Cu1 152.02(2) . 3 ?
I2 Cu1 Cu1 59.57(3) 3 3 ?
I2 Cu1 Cu1 59.55(3) . 3 ?
N3 Cu1 Cu2 104.74(16) . 3 ?
I1 Cu1 Cu2 59.38(3) . 3 ?
I2 Cu1 Cu2 60.64(3) 3 3 ?
I2 Cu1 Cu2 151.18(4) . 3 ?
Cu1 Cu1 Cu2 119.34(5) 3 3 ?
N1 Cu2 I1 108.38(17) . 7 ?
N1 Cu2 I1 108.48(16) . 3 ?
I1 Cu2 I1 119.50(3) 7 3 ?
N1 Cu2 Cu2 128.87(17) . 5 ?
I1 Cu2 Cu2 60.12(3) 7 5 ?
I1 Cu2 Cu2 59.38(3) 3 5 ?
N1 Cu2 Cu1 99.62(17) . 3 ?
I1 Cu2 Cu1 149.66(4) 7 3 ?
I1 Cu2 Cu1 59.27(3) 3 3 ?
Cu2 Cu2 Cu1 110.14(5) 5 3 ?
N1 Cu2 I2 99.96(16) . . ?
I1 Cu2 I2 103.87(3) 7 . ?
I1 Cu2 I2 114.77(4) 3 . ?
Cu2 Cu2 I2 130.89(5) 5 . ?
Cu1 Cu2 I2 58.85(3) 3 . ?
O1 Cu3 O8 171.1(2) . 2_554 ?
O1 Cu3 N4 94.8(2) . 2_554 ?
O8 Cu3 N4 83.1(2) 2_554 2_554 ?
O1 Cu3 N2 83.5(2) . . ?
O8 Cu3 N2 96.5(2) 2_554 . ?
N4 Cu3 N2 166.3(3) 2_554 . ?
O1 Cu3 O1W 97.6(2) . . ?
O8 Cu3 O1W 91.2(2) 2_554 . ?
N4 Cu3 O1W 95.5(2) 2_554 . ?
N2 Cu3 O1W 98.2(2) . . ?
Cu2 I1 Cu1 112.83(3) 7_556 . ?
Cu2 I1 Cu2 60.50(3) 7_556 3 ?
Cu1 I1 Cu2 61.35(3) . 3 ?
Cu1 I2 Cu1 60.89(3) 3 . ?
Cu1 I2 Cu2 60.51(3) 3 . ?
Cu1 I2 Cu2 120.50(3) . . ?
O2 C1 O1 126.0(6) . . ?
O2 C1 C2 119.9(6) . . ?
O1 C1 C2 114.0(6) . . ?
N2 C2 C3 121.3(6) . . ?
N2 C2 C1 115.0(5) . . ?
C3 C2 C1 123.8(6) . . ?
N1 C3 C2 121.2(6) . . ?
N1 C3 H3A 119.4 . . ?
C2 C3 H3A 119.4 . . ?
N1 C4 C5 121.3(6) . . ?
N1 C4 H4A 119.3 . . ?
C5 C4 H4A 119.3 . . ?
N2 C5 C4 121.0(6) . . ?
N2 C5 H5A 119.5 . . ?
C4 C5 H5A 119.5 . . ?
O7 C6 O8 124.5(6) . . ?
O7 C6 C7 120.7(6) . . ?
O8 C6 C7 114.8(6) . . ?
N4 C7 C8 121.5(6) . . ?
N4 C7 C6 114.9(6) . . ?
C8 C7 C6 123.6(6) . . ?
N3 C8 C7 120.6(6) . . ?
N3 C8 H8A 119.7 . . ?
C7 C8 H8A 119.7 . . ?
N3 C9 C10 122.3(6) . . ?
N3 C9 H9A 118.8 . . ?
C10 C9 H9A 118.8 . . ?
N4 C10 C9 120.4(6) . . ?
N4 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
C4 N1 C3 117.7(5) . . ?
C4 N1 Cu2 121.0(4) . . ?
C3 N1 Cu2 120.8(4) . . ?
C5 N2 C2 117.5(5) . . ?
C5 N2 Cu3 130.9(5) . . ?
C2 N2 Cu3 111.6(4) . . ?
C8 N3 C9 117.4(5) . . ?
C8 N3 Cu1 121.3(4) . . ?
C9 N3 Cu1 121.2(4) . . ?
C10 N4 C7 117.7(5) . . ?
C10 N4 Cu3 130.4(4) . 2 ?
C7 N4 Cu3 111.8(4) . 2 ?
C1 O1 Cu3 115.9(4) . . ?
Cu3 O1W H1WA 109.5 . . ?
Cu3 O1W H1WB 109.3 . . ?
H1WA O1W H1WB 108.2 . . ?
C6 O8 Cu3 115.3(4) . 2 ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        27.94
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         1.816
_refine_diff_density_min         -1.019
_refine_diff_density_rms         0.168
