# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 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_mo_dd18010_0m
_database_code_depnum_ccdc_archive 'CCDC 1838524'
_audit_update_record             
;
2018-04-20 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 F4 I2 N2 O2'
_chemical_formula_weight         746.26

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'
F F 0.0171 0.0103 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 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, -z'

_cell_length_a                   4.0465(2)
_cell_length_b                   12.2676(7)
_cell_length_c                   14.3472(8)
_cell_angle_alpha                82.585(2)
_cell_angle_beta                 82.769(2)
_cell_angle_gamma                83.758(2)
_cell_volume                     697.53(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9260
_cell_measurement_theta_min      4.678
_cell_measurement_theta_max      55.141

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.309
_shelx_estimated_absorpt_T_min   0.695
_shelx_estimated_absorpt_T_max   0.802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5347
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19042
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.339
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2691
_reflns_number_gt                2646
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0217P)²+0.5341P] 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     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2691
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0165
_refine_ls_R_factor_gt           0.0162
_refine_ls_wR_factor_ref         0.0460
_refine_ls_wR_factor_gt          0.0458
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.078 0.500 0.500 61 28 ' '
_platon_squeeze_details          
;
;




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 0.30486(3) 0.25901(2) 0.92578(2) 0.02713(8) Uani 1 1 d . . . . .
N1 N 0.5127(5) 0.46655(16) 0.85578(15) 0.0361(4) Uani 1 1 d . . . . .
O1 O 0.7204(5) 1.20041(14) 0.55584(12) 0.0399(4) Uani 1 1 d . . . . .
F1 F 0.0655(4) 0.07592(12) 0.81346(9) 0.0407(3) Uani 1 1 d . . . . .
F2 F -0.1843(4) -0.11560(11) 0.86945(10) 0.0390(3) Uani 1 1 d . . . . .
C1 C 0.8526(6) 1.09919(19) 0.53025(15) 0.0318(5) Uani 1 1 d . . . . .
C2 C 0.7993(6) 1.00015(19) 0.58548(16) 0.0330(5) Uani 1 1 d . . . . .
H2 H 0.6622 1.0007 0.6443 0.040 Uiso 1 1 calc R U . . .
C3 C 0.9428(6) 0.89931(19) 0.55651(15) 0.0309(5) Uani 1 1 d . . . . .
C4 C 0.8861(6) 0.79349(19) 0.61327(16) 0.0333(5) Uani 1 1 d . . . . .
H4 H 1.0174 0.7301 0.5929 0.040 Uiso 1 1 calc R U . . .
C5 C 0.6701(6) 0.77699(19) 0.69034(16) 0.0323(5) Uani 1 1 d . . . . .
H5 H 0.5363 0.8397 0.7112 0.039 Uiso 1 1 calc R U . . .
C6 C 0.6218(6) 0.66930(18) 0.74587(15) 0.0296(5) Uani 1 1 d . . . . .
C7 C 0.7744(7) 0.5692(2) 0.71800(19) 0.0430(6) Uani 1 1 d . . . . .
H7 H 0.9199 0.5680 0.6607 0.052 Uiso 1 1 calc R U . . .
C8 C 0.7122(7) 0.4716(2) 0.7744(2) 0.0430(6) Uani 1 1 d . . . . .
H8 H 0.8178 0.4044 0.7539 0.052 Uiso 1 1 calc R U . . .
C9 C 0.3701(6) 0.5616(2) 0.88273(18) 0.0380(5) Uani 1 1 d . . . . .
H9 H 0.2286 0.5599 0.9409 0.046 Uiso 1 1 calc R U . . .
C10 C 0.4155(6) 0.66322(19) 0.83083(17) 0.0353(5) Uani 1 1 d . . . . .
H10 H 0.3054 0.7287 0.8534 0.042 Uiso 1 1 calc R U . . .
C11 C 0.5110(7) 1.2023(2) 0.64281(18) 0.0438(6) Uani 1 1 d . . . . .
H11A H 0.3181 1.1609 0.6412 0.066 Uiso 1 1 calc R U . . .
H11B H 0.4329 1.2788 0.6526 0.066 Uiso 1 1 calc R U . . .
H11C H 0.6372 1.1682 0.6948 0.066 Uiso 1 1 calc R U . . .
C12 C 0.1307(5) 0.10310(16) 0.96999(15) 0.0245(4) Uani 1 1 d . . . . .
C13 C 0.0357(5) 0.04000(17) 0.90685(14) 0.0263(4) Uani 1 1 d . . . . .
C14 C -0.0926(5) -0.05993(17) 0.93571(15) 0.0261(4) Uani 1 1 d . . . . .


_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 C12 2.104(2) . ?
N1 C9 1.325(3) . ?
N1 C8 1.332(3) . ?
O1 C1 1.374(3) . ?
O1 C11 1.419(3) . ?
F1 C13 1.350(2) . ?
F2 C14 1.349(3) . ?
C1 C2 1.384(3) . ?
C1 C3 1.405(3) 2_776 ?
C2 C3 1.399(3) . ?
C2 H2 0.9500 . ?
C3 C1 1.405(3) 2_776 ?
C3 C4 1.465(3) . ?
C4 C5 1.329(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.471(3) . ?
C5 H5 0.9500 . ?
C6 C10 1.386(3) . ?
C6 C7 1.396(4) . ?
C7 C8 1.384(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.379(3) . ?
C12 C14 1.384(3) 2_557 ?
C13 C14 1.377(3) . ?
C14 C12 1.384(3) 2_557 ?

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
C9 N1 C8 116.8(2) . . ?
C1 O1 C11 117.57(19) . . ?
O1 C1 C2 123.7(2) . . ?
O1 C1 C3 115.91(19) . 2_776 ?
C2 C1 C3 120.4(2) . 2_776 ?
C1 C2 C3 121.4(2) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C1 118.2(2) . 2_776 ?
C2 C3 C4 122.3(2) . . ?
C1 C3 C4 119.5(2) 2_776 . ?
C5 C4 C3 126.7(2) . . ?
C5 C4 H4 116.6 . . ?
C3 C4 H4 116.6 . . ?
C4 C5 C6 125.1(2) . . ?
C4 C5 H5 117.4 . . ?
C6 C5 H5 117.4 . . ?
C10 C6 C7 116.3(2) . . ?
C10 C6 C5 120.2(2) . . ?
C7 C6 C5 123.5(2) . . ?
C8 C7 C6 119.6(2) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
N1 C8 C7 123.7(2) . . ?
N1 C8 H8 118.2 . . ?
C7 C8 H8 118.2 . . ?
N1 C9 C10 123.7(2) . . ?
N1 C9 H9 118.2 . . ?
C10 C9 H9 118.2 . . ?
C9 C10 C6 120.0(2) . . ?
C9 C10 H10 120.0 . . ?
C6 C10 H10 120.0 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C14 116.20(19) . 2_557 ?
C13 C12 I1 121.75(15) . . ?
C14 C12 I1 122.00(16) 2_557 . ?
F1 C13 C14 117.86(19) . . ?
F1 C13 C12 120.03(19) . . ?
C14 C13 C12 122.11(19) . . ?
F2 C14 C13 118.31(19) . . ?
F2 C14 C12 120.01(19) . 2_557 ?
C13 C14 C12 121.7(2) . 2_557 ?

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
C11 O1 C1 C2 -1.6(3) . . . . ?
C11 O1 C1 C3 179.7(2) . . . 2_776 ?
O1 C1 C2 C3 -179.3(2) . . . . ?
C3 C1 C2 C3 -0.7(4) 2_776 . . . ?
C1 C2 C3 C1 0.7(4) . . . 2_776 ?
C1 C2 C3 C4 -179.2(2) . . . . ?
C2 C3 C4 C5 8.6(4) . . . . ?
C1 C3 C4 C5 -171.3(2) 2_776 . . . ?
C3 C4 C5 C6 -179.6(2) . . . . ?
C4 C5 C6 C10 173.0(2) . . . . ?
C4 C5 C6 C7 -7.1(4) . . . . ?
C10 C6 C7 C8 0.5(4) . . . . ?
C5 C6 C7 C8 -179.5(2) . . . . ?
C9 N1 C8 C7 -0.3(4) . . . . ?
C6 C7 C8 N1 -0.3(5) . . . . ?
C8 N1 C9 C10 0.7(4) . . . . ?
N1 C9 C10 C6 -0.5(4) . . . . ?
C7 C6 C10 C9 -0.1(4) . . . . ?
C5 C6 C10 C9 179.8(2) . . . . ?
C14 C12 C13 F1 -179.83(19) 2_557 . . . ?
I1 C12 C13 F1 2.6(3) . . . . ?
C14 C12 C13 C14 0.5(3) 2_557 . . . ?
I1 C12 C13 C14 -177.05(16) . . . . ?
F1 C13 C14 F2 -0.7(3) . . . . ?
C12 C13 C14 F2 178.94(19) . . . . ?
F1 C13 C14 C12 179.80(19) . . . 2_557 ?
C12 C13 C14 C12 -0.6(4) . . . 2_557 ?

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
C10 H10 F2 0.95 2.61 3.490(3) 154.5 1_565

_refine_diff_density_max         0.476
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.061

_shelxl_version_number           2013-4

