# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1538298'
_audit_update_record             
;
2017-03-16 deposited with the CCDC.
2017-05-04 downloaded from the CCDC.
;
_audit_creation_date             2017-03-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cd I4, 2(C8 H12 N)'
_chemical_formula_sum            'C16 H24 Cd I4 N2'
_chemical_formula_weight         864.37
_chemical_melting_point          ?
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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   10.8728(17)
_cell_length_b                   8.4539(11)
_cell_length_c                   13.6191(18)
_cell_angle_alpha                90
_cell_angle_beta                 98.521(4)
_cell_angle_gamma                90
_cell_volume                     1238.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6518
_cell_measurement_temperature    320(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.02
_shelx_estimated_absorpt_T_max   1.000
_shelx_estimated_absorpt_T_min   0.273
_exptl_absorpt_coefficient_mu    5.870
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ABSCOR
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             788
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   1.000000
_exptl_transmission_factor_min   0.273454
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6876
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         3.025
_diffrn_ambient_temperature      320(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2101
_reflns_number_total             2538
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.145
_refine_diff_density_min         -2.148
_refine_diff_density_rms         0.322
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.221
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2538
_refine_ls_number_restraints     118
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0704
_refine_ls_restrained_S_all      1.202
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0862P)²+8.8105P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1979
_refine_ls_wR_factor_ref         0.2099
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
2. Restrained distances
 C9-C10 = C10-C11 = C1-C2 = C2-C3
 1.5 with sigma of 0.02
 N1-C1 = N2-C9
 1.47 with sigma of 0.02
 N1-C2 = C1-C3 = N2-C10 = C9-C11
 2.52 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N1 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8
\\sim N2 \\sim C9 \\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15
\\sim C16: within 1.6A with sigma of 0.02 and sigma for terminal atoms of 0.04
4. Others
 Fixed Sof: I3(0.5) N1(0.5) H1A(0.5) H1B(0.5) H1C(0.5) C1(0.5) H1D(0.5)
 H1E(0.5) C2(0.5) H2A(0.5) H2B(0.5) C3(0.5) C4(0.5) H4(0.5) C5(0.5) H5(0.5)
 C6(0.5) H6(0.5) C7(0.5) H7(0.5) C8(0.5) H8(0.5) N2(0.5) H2C(0.5) H2D(0.5)
 H2E(0.5) C9(0.5) H9A(0.5) H9B(0.5) C10(0.5) H10A(0.5) H10B(0.5) C11(0.5)
 C12(0.5) H12(0.5) C13(0.5) H13(0.5) C14(0.5) H14(0.5) C15(0.5) H15(0.5)
 C16(0.5) H16(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1D,H1E), C2(H2A,H2B), C9(H9A,H9B), C10(H10A,H10B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
5.c Fitted hexagon refined as free rotating group:
 C3(C4,C5,C6,C7,C8), C11(C12,C13,C14,C15,C16)
5.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), N2(H2C,H2D,H2E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
I1 I 0.29090(14) 0.250000 0.66117(10) 0.0886(5) Uani 1 2 d S T P A .
I2 I 0.33193(10) -0.01356(10) 0.38163(7) 0.0770(4) Uani 1 1 d . . . . .
Cd1 Cd 0.22717(13) 0.250000 0.45768(10) 0.0619(4) Uani 1 2 d S T P . .
I3 I -0.02983(17) 0.2183(6) 0.40214(12) 0.0791(16) Uani 0.5 1 d . . . A -1
N1 N -0.044(2) 0.276(5) 0.6617(11) 0.077(10) Uani 0.5 1 d D U . B -1
H1A H 0.019702 0.310021 0.633660 0.093 Uiso 0.5 1 calc GR . . B -1
H1B H -0.112567 0.328919 0.636579 0.093 Uiso 0.5 1 calc GR . . B -1
H1C H -0.055862 0.173185 0.649500 0.093 Uiso 0.5 1 calc GR . . B -1
C1 C -0.019(2) 0.302(3) 0.7688(12) 0.072(7) Uani 0.5 1 d D U . B -1
H1D H -0.091410 0.350496 0.789556 0.086 Uiso 0.5 1 calc R . . B -1
H1E H 0.049031 0.377382 0.781949 0.086 Uiso 0.5 1 calc R . . B -1
C2 C 0.015(2) 0.160(3) 0.8323(13) 0.073(6) Uani 0.5 1 d D U . B -1
H2A H 0.071022 0.094293 0.801126 0.088 Uiso 0.5 1 calc R . . B -1
H2B H -0.060164 0.098766 0.835412 0.088 Uiso 0.5 1 calc R . . B -1
C3 C 0.0742(15) 0.197(2) 0.9358(8) 0.069(5) Uani 0.5 1 d D U . B -1
C4 C 0.1868(15) 0.277(3) 0.9575(12) 0.084(6) Uani 0.5 1 d G U . B -1
H4 H 0.232114 0.301905 0.906816 0.101 Uiso 0.5 1 calc R . . B -1
C5 C 0.2318(16) 0.318(3) 1.0549(14) 0.097(7) Uani 0.5 1 d G U . B -1
H5 H 0.307211 0.371567 1.069431 0.116 Uiso 0.5 1 calc R . . B -1
C6 C 0.164(2) 0.281(3) 1.1307(10) 0.097(8) Uani 0.5 1 d G U . B -1
H6 H 0.194268 0.308558 1.195847 0.116 Uiso 0.5 1 calc R . . B -1
C7 C 0.052(2) 0.201(2) 1.1090(10) 0.088(7) Uani 0.5 1 d G U . B -1
H7 H 0.006228 0.175885 1.159648 0.106 Uiso 0.5 1 calc R . . B -1
C8 C 0.0065(15) 0.159(2) 1.0115(12) 0.082(6) Uani 0.5 1 d G U . B -1
H8 H -0.068871 0.106221 0.997033 0.099 Uiso 0.5 1 calc R . . B -1
N2 N 0.607(2) 0.235(9) 0.3748(11) 0.085(9) Uani 0.5 1 d D U . C -1
H2C H 0.668589 0.165105 0.385420 0.102 Uiso 0.5 1 calc GR . . C -1
H2D H 0.537959 0.193083 0.391159 0.102 Uiso 0.5 1 calc GR . . C -1
H2E H 0.627410 0.320957 0.411723 0.102 Uiso 0.5 1 calc GR . . C -1
C9 C 0.586(3) 0.280(5) 0.2697(14) 0.104(9) Uani 0.5 1 d D U . C -1
H9A H 0.611414 0.389178 0.264571 0.124 Uiso 0.5 1 calc R . . C -1
H9B H 0.497598 0.274580 0.246420 0.124 Uiso 0.5 1 calc R . . C -1
C10 C 0.652(4) 0.183(4) 0.2005(15) 0.106(8) Uani 0.5 1 d D U . C -1
H10A H 0.617867 0.076578 0.195714 0.127 Uiso 0.5 1 calc R . . C -1
H10B H 0.739524 0.176382 0.226116 0.127 Uiso 0.5 1 calc R . . C -1
C11 C 0.634(2) 0.261(4) 0.0972(9) 0.100(6) Uani 0.5 1 d D U . C -1
C12 C 0.712(2) 0.159(3) 0.0557(15) 0.109(8) Uani 0.5 1 d G U . C -1
H12 H 0.774447 0.104685 0.096386 0.131 Uiso 0.5 1 calc R . . C -1
C13 C 0.699(2) 0.140(3) -0.0467(16) 0.106(8) Uani 0.5 1 d G U . C -1
H13 H 0.751271 0.071865 -0.074490 0.128 Uiso 0.5 1 calc R . . C -1
C14 C 0.606(2) 0.221(3) -0.1075(10) 0.085(7) Uani 0.5 1 d G U . C -1
H14 H 0.596493 0.208135 -0.176047 0.102 Uiso 0.5 1 calc R . . C -1
C15 C 0.527(2) 0.323(3) -0.0660(13) 0.089(7) Uani 0.5 1 d G U . C -1
H15 H 0.464890 0.377227 -0.106729 0.106 Uiso 0.5 1 calc R . . C -1
C16 C 0.541(2) 0.342(3) 0.0364(14) 0.093(7) Uani 0.5 1 d G U . C -1
H16 H 0.488063 0.410049 0.064147 0.112 Uiso 0.5 1 calc R . . C -1


_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
I1 Cd1 2.7553(19) . ?
I2 Cd1 2.7720(13) . ?
Cd1 I3 2.797(2) . ?
N1 C1 1.461(17) . ?
C1 C2 1.493(17) . ?
C2 C3 1.494(17) . ?
C3 C4 1.3900 . ?
C3 C8 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C6 C7 1.3900 . ?
C7 C8 1.3900 . ?
N2 C9 1.465(19) . ?
C9 C10 1.503(18) . ?
C10 C11 1.538(18) . ?
C11 C12 1.3900 . ?
C11 C16 1.3900 . ?
C12 C13 1.3900 . ?
C13 C14 1.3900 . ?
C14 C15 1.3900 . ?
C15 C16 1.3900 . ?

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
I1 Cd1 I2 108.65(4) . . ?
I1 Cd1 I2 108.65(4) . 4_565 ?
I1 Cd1 I3 111.36(7) . . ?
I2 Cd1 I2 106.99(7) . 4_565 ?
I2 Cd1 I3 105.74(10) . . ?
I2 Cd1 I3 115.16(10) 4_565 . ?
N1 C1 C2 116.9(19) . . ?
C1 C2 C3 114.2(16) . . ?
C4 C3 C2 123.2(14) . . ?
C4 C3 C8 120.0 . . ?
C8 C3 C2 116.6(15) . . ?
C3 C4 C5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C7 C6 C5 120.0 . . ?
C6 C7 C8 120.0 . . ?
C7 C8 C3 120.0 . . ?
N2 C9 C10 117(2) . . ?
C9 C10 C11 109.5(16) . . ?
C12 C11 C10 96.1(16) . . ?
C12 C11 C16 120.0 . . ?
C16 C11 C10 137.7(18) . . ?
C11 C12 C13 120.0 . . ?
C14 C13 C12 120.0 . . ?
C13 C14 C15 120.0 . . ?
C16 C15 C14 120.0 . . ?
C15 C16 C11 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1538297'
_audit_update_record             
;
2017-03-16 deposited with the CCDC.
2017-05-04 downloaded from the CCDC.
;
_audit_creation_date             2017-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cd I4, 2(C8 H12 N)'
_chemical_formula_sum            'C16 H24 Cd I4 N2'
_chemical_formula_weight         864.37
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.7635(12)
_cell_length_b                   8.4013(8)
_cell_length_c                   13.5791(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.698(3)
_cell_angle_gamma                90
_cell_volume                     1213.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      27.515
_cell_measurement_theta_min      3.035
_shelx_estimated_absorpt_T_max   1.000
_shelx_estimated_absorpt_T_min   0.161
_exptl_absorpt_coefficient_mu    5.988
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.160778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ABSCOR
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             788
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   1.000000
_exptl_transmission_factor_min   0.160778
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9074
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.035
_diffrn_ambient_temperature      220(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4203
_reflns_number_total             4509
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.498
_refine_diff_density_min         -0.841
_refine_diff_density_rms         0.201
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.52(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         4509
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²+0.7820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1076
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.48(7)
 0.52(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
3. Restrained distances
 C1-C2 = C2-C3 = C10-C11
 1.52 with sigma of 0.02
 C9-C10
 1.51 with sigma of 0.01
4. Others
 Sof(I4')=1-FVAR(1)
 Sof(I4)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1D,H1E), C2(H2A,H2B), C9(H9A,H9B), C10(H10A,H10B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
5.c Fitted hexagon refined as free rotating group:
 C3(C4,C5,C6,C7,C8), C11(C12,C13,C14,C15,C16)
5.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), N2(H2C,H2D,H2E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
I1 I 0.70911(7) 0.2998(2) -0.16128(5) 0.0585(3) Uani 1 1 d . . . . .
I2 I 0.66057(10) 0.5427(2) 0.12364(7) 0.0494(2) Uani 1 1 d . . . . .
I3 I 0.67199(9) 0.0131(2) 0.11460(6) 0.0493(2) Uani 1 1 d . . . . .
I4 I 1.0315(3) 0.3156(17) 0.1002(4) 0.0576(16) Uani 0.79(4) 1 d . . P A 1
I4' I 1.0332(17) 0.253(5) 0.0999(14) 0.056(4) Uani 0.21(4) 1 d . . P A 2
Cd1 Cd 0.77156(7) 0.2857(2) 0.04323(5) 0.0419(2) Uani 1 1 d . . . . .
N1 N 1.0470(10) 0.2731(19) 0.8377(6) 0.060(3) Uani 1 1 d . . . . .
H1A H 1.090860 0.363053 0.846666 0.072 Uiso 1 1 calc GR . . . .
H1B H 1.091915 0.193631 0.868410 0.072 Uiso 1 1 calc GR . . . .
H1C H 0.975752 0.283613 0.862955 0.072 Uiso 1 1 calc GR . . . .
C1 C 1.0174(13) 0.2377(15) 0.7290(8) 0.054(3) Uani 1 1 d D . . . .
H1D H 0.949966 0.160238 0.717431 0.064 Uiso 1 1 calc R . . . .
H1E H 1.090772 0.192765 0.705823 0.064 Uiso 1 1 calc R . . . .
C2 C 0.9780(14) 0.3902(15) 0.6714(8) 0.052(3) Uani 1 1 d D . . . .
H2A H 1.050048 0.459761 0.671969 0.062 Uiso 1 1 calc R . . . .
H2B H 0.915115 0.446047 0.702348 0.062 Uiso 1 1 calc R . . . .
C3 C 0.9241(7) 0.3460(11) 0.5640(4) 0.046(3) Uani 1 1 d D . . . .
C4 C 0.9908(7) 0.3841(11) 0.4872(6) 0.055(3) Uani 1 1 d G . . . .
H4 H 1.067358 0.437055 0.501173 0.066 Uiso 1 1 calc R . . . .
C5 C 0.9432(10) 0.3431(13) 0.3897(5) 0.076(5) Uani 1 1 d G . . . .
H5 H 0.987849 0.368658 0.338285 0.091 Uiso 1 1 calc R . . . .
C6 C 0.8288(10) 0.2640(14) 0.3688(4) 0.072(4) Uani 1 1 d G . . . .
H6 H 0.796952 0.236585 0.303540 0.087 Uiso 1 1 calc R . . . .
C7 C 0.7621(8) 0.2259(13) 0.4456(6) 0.080(5) Uani 1 1 d G . . . .
H7 H 0.685563 0.172909 0.431683 0.097 Uiso 1 1 calc R . . . .
C8 C 0.8097(7) 0.2668(12) 0.5432(5) 0.055(3) Uani 1 1 d G . . . .
H8 H 0.765070 0.241304 0.594571 0.066 Uiso 1 1 calc R . . . .
N2 N 0.3908(10) 0.2747(19) 0.1282(6) 0.060(3) Uani 1 1 d . . . . .
H2C H 0.419545 0.192107 0.097251 0.072 Uiso 1 1 calc GR . . . .
H2D H 0.432064 0.362266 0.115367 0.072 Uiso 1 1 calc GR . . . .
H2E H 0.309173 0.287334 0.106497 0.072 Uiso 1 1 calc GR . . . .
C9 C 0.4104(15) 0.2451(15) 0.2374(8) 0.062(4) Uani 1 1 d D . . . .
H9A H 0.499869 0.236917 0.260786 0.075 Uiso 1 1 calc R . . . .
H9B H 0.372482 0.143781 0.249955 0.075 Uiso 1 1 calc R . . . .
C11 C 0.3664(9) 0.3290(11) 0.4047(4) 0.056(3) Uani 1 1 d D . . . .
C12 C 0.4604(8) 0.4007(11) 0.4715(6) 0.067(4) Uani 1 1 d G . . . .
H12 H 0.517687 0.468828 0.448248 0.080 Uiso 1 1 calc R . . . .
C13 C 0.4689(9) 0.3708(13) 0.5729(6) 0.073(5) Uani 1 1 d G . . . .
H13 H 0.531769 0.418823 0.617601 0.087 Uiso 1 1 calc R . . . .
C14 C 0.3833(11) 0.2690(13) 0.6076(5) 0.065(4) Uani 1 1 d G . . . .
H14 H 0.388960 0.248990 0.675507 0.078 Uiso 1 1 calc R . . . .
C15 C 0.2893(10) 0.1972(12) 0.5408(8) 0.086(5) Uani 1 1 d G . . . .
H15 H 0.232069 0.129159 0.564062 0.103 Uiso 1 1 calc R . . . .
C16 C 0.2809(8) 0.2272(12) 0.4394(7) 0.074(5) Uani 1 1 d G . . . .
H16 H 0.217985 0.179161 0.394709 0.088 Uiso 1 1 calc R . . . .
C10 C 0.3567(19) 0.3709(19) 0.2958(9) 0.083(6) Uani 1 1 d D . . . .
H10A H 0.269041 0.386864 0.268357 0.100 Uiso 1 1 calc R . . . .
H10B H 0.400773 0.470137 0.289249 0.100 Uiso 1 1 calc 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
I1 Cd1 2.7593(10) . ?
I2 Cd1 2.7710(11) . ?
I3 Cd1 2.7654(12) . ?
I4 Cd1 2.799(4) . ?
I4' Cd1 2.819(19) . ?
N1 C1 1.492(13) . ?
C1 C2 1.528(15) . ?
C2 C3 1.531(12) . ?
C3 C4 1.3900 . ?
C3 C8 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C6 C7 1.3900 . ?
C7 C8 1.3900 . ?
N2 C9 1.487(14) . ?
C9 C10 1.489(11) . ?
C11 C12 1.3900 . ?
C11 C16 1.3900 . ?
C11 C10 1.509(13) . ?
C12 C13 1.3900 . ?
C13 C14 1.3900 . ?
C14 C15 1.3900 . ?
C15 C16 1.3900 . ?

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
I1 Cd1 I2 108.00(4) . . ?
I1 Cd1 I3 109.88(4) . . ?
I1 Cd1 I4 110.82(12) . . ?
I1 Cd1 I4' 111.1(4) . . ?
I2 Cd1 I4 107.1(2) . . ?
I2 Cd1 I4' 116.2(9) . . ?
I3 Cd1 I2 107.12(3) . . ?
I3 Cd1 I4 113.7(3) . . ?
I3 Cd1 I4' 104.3(6) . . ?
N1 C1 C2 109.9(10) . . ?
C1 C2 C3 108.7(9) . . ?
C4 C3 C2 119.6(7) . . ?
C4 C3 C8 120.0 . . ?
C8 C3 C2 120.4(7) . . ?
C5 C4 C3 120.0 . . ?
C4 C5 C6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C6 C7 C8 120.0 . . ?
C7 C8 C3 120.0 . . ?
N2 C9 C10 113.9(11) . . ?
C12 C11 C16 120.0 . . ?
C12 C11 C10 118.3(11) . . ?
C16 C11 C10 121.6(11) . . ?
C11 C12 C13 120.0 . . ?
C14 C13 C12 120.0 . . ?
C15 C14 C13 120.0 . . ?
C16 C15 C14 120.0 . . ?
C15 C16 C11 120.0 . . ?
C9 C10 C11 112.4(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.48(7)
2 0.52(7)

