# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_khd365h
_database_code_depnum_ccdc_archive 'CCDC 1822953'
_audit_update_record             
;
2018-02-08 deposited with the CCDC.
2018-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 Cd I2 N4 O2 S2'
_chemical_formula_weight         732.71

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 '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   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   9.0805(18)
_cell_length_b                   17.501(4)
_cell_length_c                   30.181(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4796.2(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4216
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      25.00

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.029
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2784
_exptl_absorpt_coefficient_mu    3.677
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2607
_exptl_absorpt_correction_T_max  0.4600
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13290
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_sigmaI/netI    0.0682
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4216
_reflns_number_gt                2270
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0369P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4216
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0814
_refine_ls_wR_factor_gt          0.0730
_refine_ls_goodness_of_fit_ref   0.814
_refine_ls_restrained_S_all      0.814
_refine_ls_shift/su_max          0.008
_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
Cd1 Cd -0.11052(5) 0.12462(3) 0.097042(14) 0.02977(12) Uani 1 1 d . . .
I1 I -0.33316(5) 0.12385(4) 0.166983(14) 0.04215(14) Uani 1 1 d . . .
I2 I -0.30298(5) 0.12724(5) 0.023069(15) 0.05224(16) Uani 1 1 d . . .
S1 S 0.12694(18) 0.12278(14) 0.20119(5) 0.0420(4) Uani 1 1 d . . .
S2 S 0.23966(19) 0.1229(3) 0.03804(5) 0.0416(4) Uani 1 1 d . . .
O1 O 0.0964(5) 0.1231(4) 0.15218(14) 0.0448(11) Uani 1 1 d . . .
O2 O 0.0735(5) 0.1233(4) 0.04236(14) 0.0445(11) Uani 1 1 d . . .
N1 N -0.0728(7) -0.0072(3) 0.10350(17) 0.0316(14) Uani 1 1 d . . .
N2 N -0.0082(8) -0.1066(3) 0.2281(2) 0.047(2) Uani 1 1 d . . .
N3 N 0.0006(8) -0.1484(4) 0.2681(2) 0.0457(19) Uani 1 1 d . . .
N4 N 0.0742(7) -0.2430(3) 0.39353(19) 0.0322(15) Uani 1 1 d . . .
C1 C -0.0665(8) -0.0395(4) 0.1434(2) 0.0306(17) Uani 1 1 d . . .
H1 H -0.0712 -0.0076 0.1680 0.037 Uiso 1 1 calc R . .
C2 C -0.0627(8) -0.0532(4) 0.0684(2) 0.0333(17) Uani 1 1 d . . .
H2 H -0.0636 -0.0313 0.0403 0.040 Uiso 1 1 calc R . .
C3 C -0.0512(8) -0.1314(8) 0.0717(2) 0.043(2) Uani 1 1 d . . .
H3 H -0.0447 -0.1617 0.0464 0.051 Uiso 1 1 calc R . .
C4 C -0.0496(9) -0.1644(4) 0.1137(3) 0.0411(19) Uani 1 1 d . . .
H4 H -0.0461 -0.2172 0.1168 0.049 Uiso 1 1 calc R . .
C5 C -0.0531(8) -0.1183(7) 0.1508(2) 0.0352(18) Uani 1 1 d . . .
C6 C -0.0406(9) -0.1498(4) 0.1951(2) 0.0383(19) Uani 1 1 d . . .
H6 H -0.0561 -0.2017 0.1997 0.046 Uiso 1 1 calc R . .
C7 C 0.0388(9) -0.1055(4) 0.2998(2) 0.038(2) Uani 1 1 d . . .
H7 H 0.0575 -0.0541 0.2944 0.046 Uiso 1 1 calc R . .
C8 C 0.0543(8) -0.1360(6) 0.3454(2) 0.0301(19) Uani 1 1 d . . .
C9 C 0.0581(9) -0.0865(4) 0.3811(3) 0.0386(18) Uani 1 1 d . . .
H9 H 0.0542 -0.0340 0.3767 0.046 Uiso 1 1 calc R . .
C10 C 0.0676(8) -0.1163(7) 0.4231(2) 0.040(2) Uani 1 1 d . . .
H10 H 0.0704 -0.0842 0.4477 0.048 Uiso 1 1 calc R . .
C11 C 0.0730(9) -0.1960(4) 0.4282(2) 0.0380(19) Uani 1 1 d . . .
H11 H 0.0759 -0.2165 0.4566 0.046 Uiso 1 1 calc R . .
C12 C 0.0644(8) -0.2141(4) 0.3531(2) 0.0291(16) Uani 1 1 d . . .
H12 H 0.0643 -0.2472 0.3290 0.035 Uiso 1 1 calc R . .
C13 C 0.2551(11) 0.1999(8) 0.2091(7) 0.076(7) Uani 1 1 d . . .
H13A H 0.3311 0.1970 0.1871 0.113 Uiso 1 1 calc R . .
H13B H 0.2983 0.1960 0.2381 0.113 Uiso 1 1 calc R . .
H13C H 0.2044 0.2478 0.2065 0.113 Uiso 1 1 calc R . .
C14 C 0.2518(7) 0.0457(8) 0.2115(6) 0.046(4) Uani 1 1 d . . .
H14A H 0.2014 -0.0021 0.2077 0.069 Uiso 1 1 calc R . .
H14B H 0.2884 0.0492 0.2413 0.069 Uiso 1 1 calc R . .
H14C H 0.3327 0.0486 0.1911 0.069 Uiso 1 1 calc R . .
C15 C 0.3039(12) 0.2014(6) 0.0704(3) 0.058(2) Uani 1 1 d . . .
H15A H 0.2813 0.2484 0.0554 0.087 Uiso 1 1 calc R . .
H15B H 0.4085 0.1973 0.0743 0.087 Uiso 1 1 calc R . .
H15C H 0.2565 0.2008 0.0988 0.087 Uiso 1 1 calc R . .
C16 C 0.3064(12) 0.0474(5) 0.0711(3) 0.057(2) Uani 1 1 d . . .
H16A H 0.2727 0.0539 0.1010 0.086 Uiso 1 1 calc R . .
H16B H 0.4121 0.0475 0.0706 0.086 Uiso 1 1 calc R . .
H16C H 0.2707 -0.0003 0.0597 0.086 Uiso 1 1 calc 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
Cd1 0.0355(3) 0.0243(2) 0.0296(2) -0.0002(3) -0.00028(19) -0.0006(3)
I1 0.0462(3) 0.0366(2) 0.0436(3) -0.0010(3) 0.0131(2) -0.0013(3)
I2 0.0394(3) 0.0765(4) 0.0408(3) 0.0006(4) -0.0120(2) -0.0012(4)
S1 0.0348(9) 0.0520(10) 0.0392(9) -0.0005(12) 0.0005(7) 0.0006(12)
S2 0.0343(8) 0.0565(11) 0.0339(8) -0.006(2) 0.0035(7) -0.0044(11)
O1 0.042(3) 0.047(3) 0.045(3) -0.001(3) -0.010(2) -0.001(3)
O2 0.034(2) 0.064(3) 0.035(2) -0.002(3) 0.0047(19) -0.007(3)
N1 0.037(4) 0.030(3) 0.028(3) 0.005(3) 0.000(3) -0.003(3)
N2 0.082(5) 0.030(5) 0.030(3) 0.009(3) -0.006(3) -0.002(3)
N3 0.067(5) 0.041(5) 0.029(3) 0.010(3) -0.008(3) -0.001(3)
N4 0.035(4) 0.026(3) 0.036(4) 0.001(3) -0.004(3) -0.002(3)
C1 0.037(4) 0.027(4) 0.028(4) -0.003(3) 0.002(3) 0.002(4)
C2 0.039(5) 0.038(5) 0.023(4) 0.003(3) 0.000(3) 0.005(4)
C3 0.059(5) 0.037(5) 0.033(4) -0.002(5) -0.003(3) 0.006(6)
C4 0.050(5) 0.026(4) 0.048(5) -0.002(4) 0.001(4) 0.006(4)
C5 0.039(4) 0.037(5) 0.030(3) 0.008(5) -0.003(3) 0.004(5)
C6 0.053(5) 0.023(4) 0.039(4) 0.004(3) 0.005(4) 0.002(4)
C7 0.051(5) 0.031(5) 0.032(4) 0.003(3) 0.000(4) 0.001(4)
C8 0.033(4) 0.025(5) 0.033(3) 0.002(4) -0.001(3) -0.003(4)
C9 0.051(5) 0.028(4) 0.038(4) -0.001(4) -0.001(4) 0.005(4)
C10 0.051(5) 0.034(6) 0.035(4) -0.008(5) 0.004(3) 0.003(5)
C11 0.053(5) 0.034(4) 0.027(4) 0.002(3) -0.002(3) 0.006(4)
C12 0.036(4) 0.027(4) 0.024(4) -0.002(3) -0.004(3) 0.000(4)
C13 0.109(17) 0.050(10) 0.068(13) -0.027(9) -0.010(6) -0.011(6)
C14 0.026(7) 0.062(10) 0.050(10) 0.006(8) -0.008(3) 0.002(4)
C15 0.054(6) 0.053(6) 0.067(7) 0.000(5) -0.003(6) -0.009(6)
C16 0.044(6) 0.049(6) 0.079(7) -0.003(5) 0.001(6) 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
Cd1 N1 2.341(6) . ?
Cd1 O2 2.348(4) . ?
Cd1 N4 2.358(6) 3 ?
Cd1 O1 2.510(4) . ?
Cd1 I2 2.8356(8) . ?
Cd1 I1 2.9229(7) . ?
S1 O1 1.505(5) . ?
S1 C14 1.790(11) . ?
S1 C13 1.798(12) . ?
S2 O2 1.515(5) . ?
S2 C16 1.763(10) . ?
S2 C15 1.783(10) . ?
N1 C1 1.330(9) . ?
N1 C2 1.332(9) . ?
N2 C6 1.284(9) . ?
N2 N3 1.415(7) . ?
N3 C7 1.263(9) . ?
N4 C12 1.324(8) . ?
N4 C11 1.331(9) . ?
N4 Cd1 2.358(6) 3_545 ?
C1 C5 1.404(14) . ?
C1 H1 0.9300 . ?
C2 C3 1.377(15) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.450(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.484(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.381(11) . ?
C8 C12 1.390(12) . ?
C9 C10 1.374(11) . ?
C9 H9 0.9300 . ?
C10 C11 1.405(14) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 Cd1 O2 86.8(2) . . ?
N1 Cd1 N4 159.75(17) . 3 ?
O2 Cd1 N4 89.7(2) . 3 ?
N1 Cd1 O1 79.9(2) . . ?
O2 Cd1 O1 86.17(15) . . ?
N4 Cd1 O1 80.0(2) 3 . ?
N1 Cd1 I2 99.89(14) . . ?
O2 Cd1 I2 83.42(11) . . ?
N4 Cd1 I2 99.52(14) 3 . ?
O1 Cd1 I2 169.58(11) . . ?
N1 Cd1 I1 92.10(14) . . ?
O2 Cd1 I1 178.20(13) . . ?
N4 Cd1 I1 90.81(15) 3 . ?
O1 Cd1 I1 92.23(11) . . ?
I2 Cd1 I1 98.19(2) . . ?
O1 S1 C14 106.9(6) . . ?
O1 S1 C13 104.3(7) . . ?
C14 S1 C13 97.6(4) . . ?
O2 S2 C16 107.3(5) . . ?
O2 S2 C15 106.0(5) . . ?
C16 S2 C15 99.0(4) . . ?
S1 O1 Cd1 142.2(3) . . ?
S2 O2 Cd1 140.3(3) . . ?
C1 N1 C2 117.4(6) . . ?
C1 N1 Cd1 120.0(5) . . ?
C2 N1 Cd1 122.6(4) . . ?
C6 N2 N3 111.8(6) . . ?
C7 N3 N2 110.7(6) . . ?
C12 N4 C11 119.2(6) . . ?
C12 N4 Cd1 119.8(5) . 3_545 ?
C11 N4 Cd1 120.9(5) . 3_545 ?
N1 C1 C5 124.5(7) . . ?
N1 C1 H1 117.8 . . ?
C5 C1 H1 117.8 . . ?
N1 C2 C3 123.3(6) . . ?
N1 C2 H2 118.4 . . ?
C3 C2 H2 118.4 . . ?
C2 C3 C4 118.5(8) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 119.8(9) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C1 116.5(7) . . ?
C4 C5 C6 121.6(10) . . ?
C1 C5 C6 121.9(8) . . ?
N2 C6 C5 120.6(7) . . ?
N2 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
N3 C7 C8 121.0(7) . . ?
N3 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C12 119.0(7) . . ?
C9 C8 C7 120.1(8) . . ?
C12 C8 C7 121.0(7) . . ?
C10 C9 C8 118.9(8) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 118.7(8) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
N4 C11 C10 121.8(7) . . ?
N4 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
N4 C12 C8 122.3(7) . . ?
N4 C12 H12 118.8 . . ?
C8 C12 H12 118.8 . . ?
S1 C13 H13A 109.5 . . ?
S1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
S1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
S1 C14 H14A 109.5 . . ?
S1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
S2 C15 H15A 109.5 . . ?
S2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
S2 C16 H16A 109.5 . . ?
S2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
S2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 S1 O1 Cd1 128.8(6) . . . . ?
C13 S1 O1 Cd1 -128.4(7) . . . . ?
N1 Cd1 O1 S1 -92.5(6) . . . . ?
O2 Cd1 O1 S1 -179.9(6) . . . . ?
N4 Cd1 O1 S1 89.7(6) 3 . . . ?
I2 Cd1 O1 S1 177.8(3) . . . . ?
I1 Cd1 O1 S1 -0.7(6) . . . . ?
C16 S2 O2 Cd1 52.2(9) . . . . ?
C15 S2 O2 Cd1 -52.8(8) . . . . ?
N1 Cd1 O2 S2 -81.0(7) . . . . ?
N4 Cd1 O2 S2 79.1(7) 3 . . . ?
O1 Cd1 O2 S2 -0.9(7) . . . . ?
I2 Cd1 O2 S2 178.7(7) . . . . ?
I1 Cd1 O2 S2 -28(6) . . . . ?
O2 Cd1 N1 C1 136.6(6) . . . . ?
N4 Cd1 N1 C1 56.1(8) 3 . . . ?
O1 Cd1 N1 C1 49.9(6) . . . . ?
I2 Cd1 N1 C1 -140.6(5) . . . . ?
I1 Cd1 N1 C1 -41.9(6) . . . . ?
O2 Cd1 N1 C2 -46.1(6) . . . . ?
N4 Cd1 N1 C2 -126.6(6) 3 . . . ?
O1 Cd1 N1 C2 -132.8(6) . . . . ?
I2 Cd1 N1 C2 36.6(6) . . . . ?
I1 Cd1 N1 C2 135.3(6) . . . . ?
C6 N2 N3 C7 177.1(8) . . . . ?
C2 N1 C1 C5 -1.4(12) . . . . ?
Cd1 N1 C1 C5 176.0(6) . . . . ?
C1 N1 C2 C3 2.2(12) . . . . ?
Cd1 N1 C2 C3 -175.1(6) . . . . ?
N1 C2 C3 C4 -0.2(13) . . . . ?
C2 C3 C4 C5 -2.7(12) . . . . ?
C3 C4 C5 C1 3.4(11) . . . . ?
C3 C4 C5 C6 -175.4(7) . . . . ?
N1 C1 C5 C4 -1.4(12) . . . . ?
N1 C1 C5 C6 177.4(7) . . . . ?
N3 N2 C6 C5 -179.2(7) . . . . ?
C4 C5 C6 N2 162.9(8) . . . . ?
C1 C5 C6 N2 -15.8(12) . . . . ?
N2 N3 C7 C8 179.3(7) . . . . ?
N3 C7 C8 C9 -163.1(8) . . . . ?
N3 C7 C8 C12 16.5(12) . . . . ?
C12 C8 C9 C10 -1.7(12) . . . . ?
C7 C8 C9 C10 177.9(7) . . . . ?
C8 C9 C10 C11 -0.1(12) . . . . ?
C12 N4 C11 C10 -2.6(12) . . . . ?
Cd1 N4 C11 C10 173.0(6) 3_545 . . . ?
C9 C10 C11 N4 2.3(13) . . . . ?
C11 N4 C12 C8 0.6(11) . . . . ?
Cd1 N4 C12 C8 -175.0(5) 3_545 . . . ?
C9 C8 C12 N4 1.5(12) . . . . ?
C7 C8 C12 N4 -178.1(7) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.451
_refine_diff_density_min         -0.766
_refine_diff_density_rms         0.143
####################################################################### 
# 
# 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_khd292b
_database_code_depnum_ccdc_archive 'CCDC 1822954'
_audit_update_record             
;
2018-02-08 deposited with the CCDC.
2018-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 Cd I2 N4'
_chemical_formula_sum            'C12 H10 Cd I2 N4'
_chemical_formula_weight         576.45

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'
Cd Cd -0.8075 1.2024 '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   Pnma
_symmetry_space_group_name_Hall  '-P 2ac 2n'

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

_cell_length_a                   8.5800(17)
_cell_length_b                   15.794(3)
_cell_length_c                   11.736(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1590.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1450
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      24.99

_exptl_crystal_description       octahedron
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    5.247
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.3020
_exptl_absorpt_correction_T_max  0.3537
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4530
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1450
_reflns_number_gt                1109
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0537P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1450
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0917
_refine_ls_wR_factor_gt          0.0874
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_restrained_S_all      0.949
_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
Cd1 Cd 0.21793(7) 0.2500 0.50735(6) 0.0377(2) Uani 1 2 d S . .
I2 I 0.47394(8) 0.2500 0.37583(6) 0.0540(2) Uani 1 2 d S . .
I1 I 0.16663(9) 0.2500 0.73391(6) 0.0602(3) Uani 1 2 d S . .
N2 N -0.4285(5) 0.5012(4) 0.4701(5) 0.0385(13) Uani 1 1 d . . .
N1 N 0.0571(6) 0.3562(3) 0.4392(5) 0.0342(12) Uani 1 1 d . . .
C2 C 0.1018(7) 0.4067(4) 0.3541(6) 0.0384(16) Uani 1 1 d . . .
H2 H 0.1979 0.3968 0.3199 0.046 Uiso 1 1 calc R . .
C4 C -0.1317(7) 0.4865(4) 0.3619(6) 0.0366(14) Uani 1 1 d . . .
H4 H -0.1934 0.5311 0.3366 0.044 Uiso 1 1 calc R . .
C5 C -0.1838(6) 0.4336(4) 0.4474(5) 0.0310(14) Uani 1 1 d . . .
C1 C -0.0854(7) 0.3698(4) 0.4835(6) 0.0360(15) Uani 1 1 d . . .
H1 H -0.1194 0.3342 0.5415 0.043 Uiso 1 1 calc R . .
C3 C 0.0128(7) 0.4724(5) 0.3147(5) 0.0401(16) Uani 1 1 d . . .
H3 H 0.0496 0.5071 0.2566 0.048 Uiso 1 1 calc R . .
C6 C -0.3368(7) 0.4431(5) 0.5007(5) 0.0372(15) Uani 1 1 d . . .
H6 H -0.3669 0.4059 0.5579 0.045 Uiso 1 1 calc 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
Cd1 0.0319(3) 0.0353(4) 0.0459(4) 0.000 0.0043(3) 0.000
I2 0.0437(4) 0.0470(4) 0.0712(5) 0.000 0.0209(3) 0.000
I1 0.0626(5) 0.0767(6) 0.0414(4) 0.000 -0.0043(3) 0.000
N2 0.032(2) 0.048(3) 0.036(3) 0.002(3) 0.000(2) 0.009(3)
N1 0.033(3) 0.031(3) 0.038(3) -0.001(3) 0.003(2) 0.004(2)
C2 0.031(3) 0.050(4) 0.034(4) -0.002(3) 0.005(3) 0.000(3)
C4 0.038(3) 0.035(4) 0.037(4) 0.002(3) -0.008(3) -0.001(3)
C5 0.032(3) 0.032(3) 0.029(3) -0.005(3) -0.002(2) 0.002(3)
C1 0.035(3) 0.039(4) 0.034(4) -0.003(3) 0.003(3) -0.003(3)
C3 0.044(4) 0.045(4) 0.032(4) 0.003(3) 0.001(3) -0.004(3)
C6 0.036(3) 0.044(4) 0.032(3) -0.007(3) 0.003(3) 0.005(3)

_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 N1 2.315(5) 7_565 ?
Cd1 N1 2.315(5) . ?
Cd1 I2 2.6846(10) . ?
Cd1 I1 2.6951(12) . ?
N2 C6 1.260(8) . ?
N2 N2 1.415(10) 5_466 ?
N1 C2 1.334(9) . ?
N1 C1 1.345(7) . ?
C2 C3 1.368(10) . ?
C2 H2 0.9300 . ?
C4 C3 1.377(9) . ?
C4 C5 1.380(9) . ?
C4 H4 0.9300 . ?
C5 C1 1.381(9) . ?
C5 C6 1.461(8) . ?
C1 H1 0.9300 . ?
C3 H3 0.9300 . ?
C6 H6 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 Cd1 N1 92.9(3) 7_565 . ?
N1 Cd1 I2 106.80(13) 7_565 . ?
N1 Cd1 I2 106.80(13) . . ?
N1 Cd1 I1 104.10(13) 7_565 . ?
N1 Cd1 I1 104.10(13) . . ?
I2 Cd1 I1 134.49(4) . . ?
C6 N2 N2 112.4(7) . 5_466 ?
C2 N1 C1 117.1(5) . . ?
C2 N1 Cd1 121.4(4) . . ?
C1 N1 Cd1 121.6(4) . . ?
N1 C2 C3 123.1(6) . . ?
N1 C2 H2 118.5 . . ?
C3 C2 H2 118.5 . . ?
C3 C4 C5 119.1(6) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C1 117.8(5) . . ?
C4 C5 C6 122.6(6) . . ?
C1 C5 C6 119.6(6) . . ?
N1 C1 C5 123.6(6) . . ?
N1 C1 H1 118.2 . . ?
C5 C1 H1 118.2 . . ?
C2 C3 C4 119.3(6) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
N2 C6 C5 120.9(6) . . ?
N2 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cd1 N1 C2 -112.0(5) 7_565 . . . ?
I2 Cd1 N1 C2 -3.5(5) . . . . ?
I1 Cd1 N1 C2 142.7(5) . . . . ?
N1 Cd1 N1 C1 68.0(5) 7_565 . . . ?
I2 Cd1 N1 C1 176.5(4) . . . . ?
I1 Cd1 N1 C1 -37.4(5) . . . . ?
C1 N1 C2 C3 2.9(10) . . . . ?
Cd1 N1 C2 C3 -177.2(5) . . . . ?
C3 C4 C5 C1 1.6(9) . . . . ?
C3 C4 C5 C6 -178.8(6) . . . . ?
C2 N1 C1 C5 -1.6(9) . . . . ?
Cd1 N1 C1 C5 178.4(5) . . . . ?
C4 C5 C1 N1 -0.6(10) . . . . ?
C6 C5 C1 N1 179.8(6) . . . . ?
N1 C2 C3 C4 -1.9(10) . . . . ?
C5 C4 C3 C2 -0.5(10) . . . . ?
N2 N2 C6 C5 178.8(7) 5_466 . . . ?
C4 C5 C6 N2 -0.1(9) . . . . ?
C1 C5 C6 N2 179.5(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
C3 H3 N2 0.93 2.67 3.410(8) 137.2 6_656

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.241
_refine_diff_density_min         -0.954
_refine_diff_density_rms         0.175
