# Electronic Supplementary Material (ESI) for Analyst.
# 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_L
_database_code_depnum_ccdc_archive 'CCDC 1534470'
_audit_update_record             
;
2017-02-23 deposited with the CCDC.
2017-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H42 N2, 2(I)'
_chemical_formula_sum            'C42 H42 I2 N2'
_chemical_formula_weight         828.58

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           178
_space_group_name_H-M_alt        'P 61 2 2'
_space_group_name_Hall           'P 61 2 (0 0 -1)'

_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, x, z+1/6'
'-y, -x, -z+5/6'
'-y, x-y, z+1/3'
'-x, -x+y, -z+2/3'
'x-y, -y, -z'
'-x, -y, z+1/2'
'-x+y, y, -z+1/2'
'x, x-y, -z+1/6'
'y, -x+y, z+5/6'
'-x+y, -x, z+2/3'
'y, x, -z+1/3'

_cell_length_a                   15.6598(11)
_cell_length_b                   15.6598(11)
_cell_length_c                   34.080(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7237.7(13)
_cell_formula_units_Z            6
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2887
_cell_measurement_theta_min      3.1460
_cell_measurement_theta_max      18.4140

_exptl_crystal_description       plate
_exptl_crystal_colour            'orange red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_F_000             2484.0
_exptl_transmission_factor_min   0.678
_exptl_transmission_factor_max   0.747
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    1.327
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD and area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22856
_diffrn_reflns_av_unetI/netI     0.1265
_diffrn_reflns_av_R_equivalents  0.1630
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         3.063
_diffrn_reflns_theta_max         28.894
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5814
_reflns_number_gt                2029
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.653
_reflns_Friedel_fraction_max     0.877
_reflns_Friedel_fraction_full    0.999

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1400P)²+0.3538P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.14(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5814
_refine_ls_number_parameters     212
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1956
_refine_ls_R_factor_gt           0.1231
_refine_ls_wR_factor_ref         0.3489
_refine_ls_wR_factor_gt          0.3163
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.098
_refine_ls_shift/su_mean         0.014

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
I0AA I 0.35406(15) 0.30453(14) 0.45176(5) 0.1441(9) Uani 1 1 d . . . . .
C15 C 0.6335(11) 0.4674(8) 0.5591(3) 0.059(3) Uani 1 1 d . . . . .
H15 H 0.6737 0.5305 0.5492 0.071 Uiso 1 1 calc R U . . .
C16 C 0.6789(8) 0.4137(9) 0.5718(3) 0.054(3) Uani 1 1 d . . . . .
C18 C 0.7784(11) 0.4591(10) 0.5714(3) 0.067(3) Uani 1 1 d . . . . .
H18 H 0.8122 0.5237 0.5622 0.080 Uiso 1 1 calc R U . . .
C10 C 0.5355(11) 0.5920(9) 0.5365(3) 0.068(4) Uani 1 1 d . . . . .
N1 N 0.3895(8) 0.4537(9) 0.5548(3) 0.073(3) Uani 1 1 d . . . . .
C9 C 0.4463(14) 0.6092(11) 0.5314(5) 0.086(4) Uani 1 1 d . . . . .
C11 C 0.4879(11) 0.4941(13) 0.5508(4) 0.082(4) Uani 1 1 d . . . . .
C6 C 0.2595(16) 0.6007(14) 0.5337(4) 0.096(5) Uani 1 1 d . . . . .
H6 H 0.1983 0.5969 0.5342 0.116 Uiso 1 1 calc R U . . .
C3 C 0.4460(11) 0.6973(11) 0.5175(3) 0.067(3) Uani 1 1 d . . . . .
C13 C 0.5852(11) 0.5960(11) 0.4936(3) 0.072(4) Uani 1 1 d . . . . .
H13A H 0.6550 0.6232 0.4966 0.109 Uiso 1 1 calc R U . . .
H13B H 0.5730 0.6367 0.4760 0.109 Uiso 1 1 calc R U . . .
H13C H 0.5566 0.5306 0.4830 0.109 Uiso 1 1 calc R U . . .
C23 C 0.3545(15) 0.6907(12) 0.5218(3) 0.089(5) Uani 1 1 d . . . . .
C14 C 0.5327(12) 0.4317(10) 0.5604(4) 0.080(4) Uani 1 1 d . . . . .
H14 H 0.4912 0.3663 0.5675 0.096 Uiso 1 1 calc R U . . .
C5 C 0.330(2) 0.765(2) 0.5099(5) 0.128(9) Uani 1 1 d . . . . .
H5 H 0.2683 0.7603 0.5098 0.153 Uiso 1 1 calc R U . . .
C7 C 0.2766(15) 0.5219(17) 0.5442(5) 0.105(6) Uani 1 1 d . . . . .
H7 H 0.2235 0.4615 0.5517 0.126 Uiso 1 1 calc R U . . .
C8 C 0.3656(10) 0.5329(12) 0.5434(4) 0.069(3) Uani 1 1 d . . . . .
C21 C 0.530(2) 0.7842(14) 0.5051(4) 0.120(8) Uani 1 1 d . . . . .
H21 H 0.5922 0.7898 0.5037 0.144 Uiso 1 1 calc R U . . .
C12 C 0.6133(12) 0.6719(14) 0.5696(4) 0.087(4) Uani 1 1 d . . . . .
H12A H 0.5765 0.6830 0.5894 0.131 Uiso 1 1 calc R U . . .
H12B H 0.6573 0.7331 0.5568 0.131 Uiso 1 1 calc R U . . .
H12C H 0.6507 0.6453 0.5814 0.131 Uiso 1 1 calc R U . . .
C20 C 0.3150(13) 0.3567(16) 0.5676(6) 0.145(9) Uani 1 1 d D U . . .
H20A H 0.3278 0.3108 0.5533 0.174 Uiso 1 1 calc R U . . .
H20B H 0.2531 0.3477 0.5576 0.174 Uiso 1 1 calc R U . . .
C17 C 0.6298(16) 0.3149(8) 0.5833 0.066(5) Uani 1 2 d S T P . .
H17 H 0.5612 0.2806 0.5833 0.079 Uiso 1 2 calc R U P . .
C19 C 0.8349(11) 0.4175(6) 0.5833 0.057(4) Uani 1 2 d S T P . .
H19 H 0.9035 0.4518 0.5833 0.069 Uiso 1 2 calc R U P . .
C22 C 0.293(2) 0.318(3) 0.6101(5) 0.201(14) Uani 1 1 d D U . . .
H22A H 0.3266 0.2816 0.6154 0.302 Uiso 1 1 calc R U . . .
H22B H 0.2237 0.2755 0.6134 0.302 Uiso 1 1 calc R U . . .
H22C H 0.3166 0.3725 0.6279 0.302 Uiso 1 1 calc R U . . .
C25 C 0.425(2) 0.849(2) 0.4981(5) 0.125(8) Uani 1 1 d . . . . .
H25 H 0.4203 0.9040 0.4915 0.150 Uiso 1 1 calc R U . . .
C24 C 0.5135(17) 0.8638(11) 0.4948(4) 0.092(5) Uani 1 1 d . . . . .
H24 H 0.5647 0.9240 0.4861 0.110 Uiso 1 1 calc R 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
C15 C14 1.39(2) . ?
C15 C16 1.414(17) . ?
C16 C18 1.351(18) . ?
C16 C17 1.396(16) . ?
C18 C19 1.397(16) . ?
C10 C11 1.42(2) . ?
C10 C9 1.56(2) . ?
C10 C13 1.641(15) . ?
C10 C12 1.67(2) . ?
N1 C11 1.349(19) . ?
N1 C20 1.45(2) . ?
N1 C8 1.513(18) . ?
C9 C8 1.30(2) . ?
C9 C3 1.46(2) . ?
C11 C14 1.50(2) . ?
C6 C7 1.43(3) . ?
C6 C23 1.51(3) . ?
C3 C23 1.39(2) . ?
C3 C21 1.40(3) . ?
C23 C5 1.45(3) . ?
C5 C25 1.46(4) . ?
C7 C8 1.32(2) . ?
C21 C24 1.44(3) . ?
C20 C22 1.5400(13) . ?
C17 C16 1.396(16) 9_556 ?
C19 C18 1.397(16) 9_556 ?
C25 C24 1.29(3) . ?

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
C14 C15 C16 124.0(11) . . ?
C18 C16 C17 116.0(13) . . ?
C18 C16 C15 118.3(12) . . ?
C17 C16 C15 125.7(13) . . ?
C16 C18 C19 125.7(13) . . ?
C11 C10 C9 101.1(12) . . ?
C11 C10 C13 109.4(12) . . ?
C9 C10 C13 110.1(11) . . ?
C11 C10 C12 111.7(10) . . ?
C9 C10 C12 109.0(11) . . ?
C13 C10 C12 114.7(11) . . ?
C11 N1 C20 130.9(12) . . ?
C11 N1 C8 106.4(11) . . ?
C20 N1 C8 122.6(12) . . ?
C8 C9 C3 120.8(15) . . ?
C8 C9 C10 110.5(11) . . ?
C3 C9 C10 128.7(15) . . ?
N1 C11 C10 113.7(12) . . ?
N1 C11 C14 118.2(13) . . ?
C10 C11 C14 128.1(14) . . ?
C7 C6 C23 110.5(17) . . ?
C23 C3 C21 122.5(16) . . ?
C23 C3 C9 112.6(14) . . ?
C21 C3 C9 124.6(16) . . ?
C3 C23 C5 126(2) . . ?
C3 C23 C6 126.7(15) . . ?
C5 C23 C6 107(2) . . ?
C15 C14 C11 122.8(13) . . ?
C23 C5 C25 104(2) . . ?
C8 C7 C6 121.6(19) . . ?
C9 C8 C7 127.3(15) . . ?
C9 C8 N1 108.1(11) . . ?
C7 C8 N1 124.5(15) . . ?
C3 C21 C24 115(2) . . ?
N1 C20 C22 127(2) . . ?
C16 C17 C16 123.0(18) 9_556 . ?
C18 C19 C18 113.4(16) 9_556 . ?
C24 C25 C5 135(2) . . ?
C25 C24 C21 118(2) . . ?

_refine_diff_density_max         0.702
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.157

