# 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_72
_database_code_depnum_ccdc_archive 'CCDC 1439857'
_audit_update_record             
;
2016-01-27 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;
#=====================================================================


_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
4(C5 H Cd0.75 O4), 4(C2.50 H2.5 N0.50), 2(H2 O)
;
_chemical_formula_sum            'C30 H18 Cd3 N2 O18'
_chemical_formula_weight         1031.66

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'
Cd Cd 0.1185 4.6533 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           72
_space_group_name_H-M_alt        'I b a m'
_space_group_name_Hall           '-I 2 2c'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   20.7803(12)
_cell_length_b                   7.9154(8)
_cell_length_c                   17.299(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2845.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00(13)
_cell_measurement_reflns_used    797
_cell_measurement_theta_min      4.2420
_cell_measurement_theta_max      73.3880

_exptl_crystal_description       Prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.408
_exptl_crystal_F_000             2000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    18.701
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.127
_exptl_absorpt_correction_T_max  0.473
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100.00(13)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            3992
_diffrn_reflns_av_unetI/netI     0.0733
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.113
_diffrn_reflns_theta_max         88.787
_diffrn_reflns_theta_full        67.680
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1645
_reflns_number_gt                990
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 The H atoms of lattice water molecule were included from the
 difmap. The O-H and H-H distances were restrained by the DFIX commmand.
 
 The C-C and C-N distances of the diprotonated 4,4'-bipyridinium cation were 
 restrained by the SADI command.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0355P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1645
_refine_ls_number_parameters     155
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1067
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.998
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.5000 0.0000 0.2500 0.0199(2) Uani 1 4 d S T P . .
Cd2 Cd 0.30182(3) 0.0000 0.2500 0.0216(2) Uani 1 2 d S T P . .
O11 O 0.2454(3) 0.4310(7) 0.3600(3) 0.0515(16) Uani 1 1 d . . . . .
O12 O 0.3152(2) 0.2797(5) 0.2924(2) 0.0242(10) Uani 1 1 d . . . . .
O13 O 0.3931(2) -0.0244(6) 0.3304(3) 0.0275(12) Uani 1 1 d . . . . .
O14 O 0.4624(2) 0.1861(6) 0.3389(3) 0.0328(12) Uani 1 1 d . . . . .
C10 C 0.2974(4) 0.3296(11) 0.5000 0.0165(19) Uani 1 2 d S T P . .
H10A H 0.2623 0.4026 0.5000 0.020 Uiso 1 2 calc R U P . .
C11 C 0.3233(3) 0.2757(7) 0.4299(3) 0.0158(13) Uani 1 1 d . . . . .
C12 C 0.3784(3) 0.1742(8) 0.4301(3) 0.0174(13) Uani 1 1 d . . . . .
C13 C 0.4051(4) 0.1299(11) 0.5000 0.021(2) Uani 1 2 d S T P . .
H13A H 0.4429 0.0672 0.5000 0.025 Uiso 1 2 calc R U P . .
C14 C 0.2935(3) 0.3330(8) 0.3554(4) 0.0196(14) Uani 1 1 d . . . . .
C15 C 0.4125(3) 0.1095(10) 0.3597(4) 0.0250(17) Uani 1 1 d . . . . .
N21 N 0.3648(6) 0.7162(15) 0.5634(7) 0.040(4) Uani 0.5 1 d D . P A 1
H21A H 0.3313 0.7696 0.5794 0.048 Uiso 0.5 1 calc R U P A 1
C20 C 0.4036(6) 0.6396(16) 0.6167(9) 0.036(4) Uani 0.5 1 d D . P A 1
H20A H 0.3937 0.6457 0.6690 0.043 Uiso 0.5 1 calc R U P A 1
C21 C 0.4572(7) 0.5536(18) 0.5925(8) 0.038(4) Uani 0.5 1 d D . P A 1
H21B H 0.4843 0.5008 0.6280 0.046 Uiso 0.5 1 calc R U P A 1
C22 C 0.4701(6) 0.5474(15) 0.5144(7) 0.030(5) Uani 0.5 1 d D . P A 1
C23 C 0.4315(6) 0.6301(19) 0.4615(9) 0.049(5) Uani 0.5 1 d D . P A 1
H23A H 0.4426 0.6305 0.4095 0.058 Uiso 0.5 1 calc R U P A 1
C24 C 0.3770(6) 0.711(2) 0.4857(8) 0.034(5) Uani 0.5 1 d D . P A 1
H24A H 0.3492 0.7616 0.4505 0.041 Uiso 0.5 1 calc R U P A 1
O1W O 0.4303(10) 0.5000 0.7500 0.234(10) Uani 1 2 d DS T P . .
H1 H 0.394(3) 0.43(2) 0.720(12) 0.351 Uiso 1 1 d D U . . .


_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
Cd1 O14 2.268(4) . ?
Cd1 O14 2.268(4) 8_445 ?
Cd1 O14 2.268(4) 2_655 ?
Cd1 O14 2.268(5) 7_545 ?
Cd1 O13 2.628(4) 2_655 ?
Cd1 O13 2.628(4) 8_445 ?
Cd1 O13 2.628(4) 7_545 ?
Cd1 O13 2.628(4) . ?
Cd2 O11 2.209(4) 13 ?
Cd2 O11 2.209(4) 12_655 ?
Cd2 O12 2.348(4) 8_445 ?
Cd2 O12 2.348(4) . ?
Cd2 O13 2.361(4) 8_445 ?
Cd2 O13 2.361(4) . ?
O11 C14 1.267(7) . ?
O11 Cd2 2.210(4) 13 ?
O12 C14 1.253(7) . ?
O13 C15 1.241(8) . ?
O14 C15 1.255(8) . ?
C10 C11 1.393(7) . ?
C10 C11 1.393(7) 10_556 ?
C10 H10A 0.9300 . ?
C11 C12 1.398(8) . ?
C11 C14 1.500(8) . ?
C12 C13 1.376(7) . ?
C12 C15 1.499(8) . ?
C13 C12 1.376(7) 10_556 ?
C13 H13A 0.9300 . ?
N21 C20 1.366(9) . ?
N21 C24 1.369(9) . ?
N21 H21A 0.8600 . ?
C20 C21 1.371(9) . ?
C20 H20A 0.9300 . ?
C21 C22 1.379(9) . ?
C21 H21B 0.9300 . ?
C22 C23 1.381(8) . ?
C22 C22 1.53(3) 9_666 ?
C23 C24 1.368(9) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9300 . ?
O1W H1 1.06(5) . ?

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
O14 Cd1 O14 139.7(2) . 8_445 ?
O14 Cd1 O14 94.6(2) . 2_655 ?
O14 Cd1 O14 99.0(2) 8_445 2_655 ?
O14 Cd1 O14 99.0(2) . 7_545 ?
O14 Cd1 O14 94.6(2) 8_445 7_545 ?
O14 Cd1 O14 139.7(2) 2_655 7_545 ?
O14 Cd1 O13 83.34(15) . 2_655 ?
O14 Cd1 O13 134.24(15) 8_445 2_655 ?
O14 Cd1 O13 52.97(15) 2_655 2_655 ?
O14 Cd1 O13 91.18(16) 7_545 2_655 ?
O14 Cd1 O13 91.18(16) . 8_445 ?
O14 Cd1 O13 52.97(15) 8_445 8_445 ?
O14 Cd1 O13 134.24(15) 2_655 8_445 ?
O14 Cd1 O13 83.34(15) 7_545 8_445 ?
O13 Cd1 O13 171.6(2) 2_655 8_445 ?
O14 Cd1 O13 134.24(15) . 7_545 ?
O14 Cd1 O13 83.34(15) 8_445 7_545 ?
O14 Cd1 O13 91.18(16) 2_655 7_545 ?
O14 Cd1 O13 52.97(15) 7_545 7_545 ?
O13 Cd1 O13 64.64(19) 2_655 7_545 ?
O13 Cd1 O13 116.0(2) 8_445 7_545 ?
O14 Cd1 O13 52.97(15) . . ?
O14 Cd1 O13 91.18(16) 8_445 . ?
O14 Cd1 O13 83.34(15) 2_655 . ?
O14 Cd1 O13 134.24(15) 7_545 . ?
O13 Cd1 O13 116.0(2) 2_655 . ?
O13 Cd1 O13 64.64(19) 8_445 . ?
O13 Cd1 O13 171.6(2) 7_545 . ?
O11 Cd2 O11 127.2(3) 13 12_655 ?
O11 Cd2 O12 90.97(18) 13 8_445 ?
O11 Cd2 O12 95.07(18) 12_655 8_445 ?
O11 Cd2 O12 95.07(18) 13 . ?
O11 Cd2 O12 90.96(18) 12_655 . ?
O12 Cd2 O12 166.4(2) 8_445 . ?
O11 Cd2 O13 80.18(18) 13 8_445 ?
O11 Cd2 O13 152.23(19) 12_655 8_445 ?
O12 Cd2 O13 78.34(15) 8_445 8_445 ?
O12 Cd2 O13 90.68(16) . 8_445 ?
O11 Cd2 O13 152.23(19) 13 . ?
O11 Cd2 O13 80.18(18) 12_655 . ?
O12 Cd2 O13 90.68(16) 8_445 . ?
O12 Cd2 O13 78.34(15) . . ?
O13 Cd2 O13 73.0(2) 8_445 . ?
C14 O11 Cd2 116.6(4) . 13 ?
C14 O12 Cd2 123.1(4) . . ?
C15 O13 Cd2 115.5(4) . . ?
C15 O13 Cd1 83.1(4) . . ?
Cd2 O13 Cd1 111.17(17) . . ?
C15 O14 Cd1 99.5(4) . . ?
C11 C10 C11 121.0(8) . 10_556 ?
C11 C10 H10A 119.5 . . ?
C11 C10 H10A 119.5 10_556 . ?
C10 C11 C12 119.3(6) . . ?
C10 C11 C14 119.7(6) . . ?
C12 C11 C14 120.9(5) . . ?
C13 C12 C11 118.6(6) . . ?
C13 C12 C15 115.9(6) . . ?
C11 C12 C15 125.5(5) . . ?
C12 C13 C12 123.0(8) 10_556 . ?
C12 C13 H13A 118.5 10_556 . ?
C12 C13 H13A 118.5 . . ?
O12 C14 O11 122.9(6) . . ?
O12 C14 C11 119.8(6) . . ?
O11 C14 C11 117.2(6) . . ?
O13 C15 O14 124.2(6) . . ?
O13 C15 C12 118.0(6) . . ?
O14 C15 C12 117.4(6) . . ?
C20 N21 C24 122.6(13) . . ?
C20 N21 H21A 118.7 . . ?
C24 N21 H21A 118.7 . . ?
N21 C20 C21 119.7(14) . . ?
N21 C20 H20A 120.1 . . ?
C21 C20 H20A 120.1 . . ?
C20 C21 C22 118.3(14) . . ?
C20 C21 H21B 120.9 . . ?
C22 C21 H21B 120.9 . . ?
C21 C22 C23 121.3(14) . . ?
C21 C22 C22 119.5(13) . 9_666 ?
C23 C22 C22 119.2(14) . 9_666 ?
C24 C23 C22 120.1(14) . . ?
C24 C23 H23A 120.0 . . ?
C22 C23 H23A 120.0 . . ?
C23 C24 N21 117.9(14) . . ?
C23 C24 H24A 121.1 . . ?
N21 C24 H24A 121.1 . . ?

_refine_diff_density_max         1.336
_refine_diff_density_min         -1.193
_refine_diff_density_rms         0.162

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 'hydrothermal reaction'
_chemical_properties_physical    'Light-sensitive, Photo-sensitive'
_exptl_crystal_preparation       Luminescent
