# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_AGHadam_0m
_database_code_depnum_ccdc_archive 'CCDC 1915890'
loop_
_audit_author_name
_audit_author_address
'Ana Garcia Herraiz'
;ICIQ
Spain
;
_audit_update_record             
;
2019-05-14 deposited with the CCDC.	2019-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H16 I2 O2'
_chemical_formula_weight         446.05

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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.782(3)
_cell_length_b                   12.620(3)
_cell_length_c                   11.033(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.298(7)
_cell_angle_gamma                90
_cell_volume                     1440.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6590
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      30.92

_exptl_crystal_description       block
_exptl_crystal_colour            grey
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.056
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    4.351
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5887
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   SADABS-2014/4
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            14791
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.511
_diffrn_reflns_theta_max         31.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4563
_reflns_number_gt                3929
_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 v2014.9-0'
_computing_cell_refinement       'Bruker APEX2 v2014.9-0'
_computing_data_reduction        'Bruker APEX2 v2014.9-0'
_computing_structure_solution    Sir2014
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'shelXle (Hübschle, Sheldrick and Dittirch, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0454P)²+1.7012P] 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_number_reflns         4563
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0928
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_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
I1 I 0.35657(2) 0.28578(2) 0.68921(2) 0.04713(8) Uani 1 1 d . . . . .
I2 I 0.18159(3) 0.52797(2) 0.63949(2) 0.05511(9) Uani 1 1 d . . . . .
O1 O 0.0916(3) 0.2994(3) 0.3759(3) 0.0601(7) Uani 1 1 d . . . . .
O2 O 0.2630(2) 0.40758(19) 0.4056(2) 0.0425(5) Uani 1 1 d . . . . .
C1 C 0.1860(3) 0.3667(2) 0.5802(3) 0.0368(6) Uani 1 1 d . . . . .
H1 H 0.111622 0.330844 0.596326 0.044 Uiso 1 1 calc R U . . .
C2 C 0.1739(3) 0.3543(2) 0.4415(3) 0.0355(5) Uani 1 1 d . . . . .
C3 C 0.2764(3) 0.3978(2) 0.2758(3) 0.0362(5) Uani 1 1 d . . . . .
C4 C 0.3941(4) 0.4651(4) 0.2791(4) 0.0553(9) Uani 1 1 d . . . . .
H4A H 0.468378 0.438533 0.343667 0.066 Uiso 1 1 calc R U . . .
H4AB H 0.378785 0.537682 0.299998 0.066 Uiso 1 1 calc R U . . .
C5 C 0.4213(5) 0.4615(4) 0.1499(4) 0.0640(11) Uani 1 1 d . . . . .
H5 H 0.497424 0.504868 0.152588 0.077 Uiso 1 1 calc R U . . .
C6 C 0.3057(6) 0.5052(5) 0.0513(5) 0.0793(15) Uani 1 1 d . . . . .
H6A H 0.321988 0.504158 -0.030834 0.095 Uiso 1 1 calc R U . . .
H6AB H 0.290560 0.578031 0.071431 0.095 Uiso 1 1 calc R U . . .
C7 C 0.1862(5) 0.4373(6) 0.0479(4) 0.0829(17) Uani 1 1 d . . . . .
H7 H 0.111046 0.464341 -0.017020 0.099 Uiso 1 1 calc R U . . .
C8 C 0.1605(4) 0.4427(4) 0.1787(4) 0.0603(10) Uani 1 1 d . . . . .
H8A H 0.146387 0.515617 0.199365 0.072 Uiso 1 1 calc R U . . .
H8AB H 0.083837 0.402061 0.177770 0.072 Uiso 1 1 calc R U . . .
C9 C 0.3026(5) 0.2837(3) 0.2467(4) 0.0618(10) Uani 1 1 d . . . . .
H9A H 0.227961 0.240016 0.244135 0.074 Uiso 1 1 calc R U . . .
H9AB H 0.375908 0.256340 0.311751 0.074 Uiso 1 1 calc R U . . .
C10 C 0.3314(6) 0.2812(4) 0.1182(5) 0.0799(15) Uani 1 1 d . . . . .
H10 H 0.348881 0.207959 0.098509 0.096 Uiso 1 1 calc R U . . .
C11 C 0.2120(6) 0.3208(6) 0.0186(5) 0.095(2) Uani 1 1 d . . . . .
H11A H 0.138032 0.277247 0.019155 0.114 Uiso 1 1 calc R U . . .
H11B H 0.225660 0.316002 -0.064475 0.114 Uiso 1 1 calc R U . . .
C12 C 0.4463(5) 0.3487(5) 0.1187(5) 0.0776(14) Uani 1 1 d . . . . .
H12A H 0.462104 0.345929 0.036403 0.093 Uiso 1 1 calc R U . . .
H12B H 0.522331 0.321898 0.180766 0.093 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
I1 C1 2.152(3) . ?
I2 C1 2.142(3) . ?
O1 C2 1.197(4) . ?
O2 C2 1.321(4) . ?
O2 C3 1.483(4) . ?
C1 C2 1.508(4) . ?
C3 C8 1.510(5) . ?
C3 C4 1.518(5) . ?
C3 C9 1.519(5) . ?
C4 C5 1.535(5) . ?
C5 C12 1.507(7) . ?
C5 C6 1.510(8) . ?
C6 C7 1.540(8) . ?
C7 C8 1.546(6) . ?
C7 C11 1.548(9) . ?
C9 C10 1.534(7) . ?
C10 C12 1.502(8) . ?
C10 C11 1.523(9) . ?

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
C2 O2 C3 121.5(2) . . ?
C2 C1 I2 114.0(2) . . ?
C2 C1 I1 109.6(2) . . ?
I2 C1 I1 111.67(13) . . ?
O1 C2 O2 126.3(3) . . ?
O1 C2 C1 120.8(3) . . ?
O2 C2 C1 112.8(2) . . ?
O2 C3 C8 111.6(3) . . ?
O2 C3 C4 103.7(2) . . ?
C8 C3 C4 109.1(3) . . ?
O2 C3 C9 110.9(3) . . ?
C8 C3 C9 111.8(3) . . ?
C4 C3 C9 109.3(3) . . ?
C3 C4 C5 109.7(3) . . ?
C12 C5 C6 110.2(4) . . ?
C12 C5 C4 109.5(4) . . ?
C6 C5 C4 108.9(4) . . ?
C5 C6 C7 109.3(4) . . ?
C6 C7 C8 108.7(4) . . ?
C6 C7 C11 109.6(5) . . ?
C8 C7 C11 109.1(4) . . ?
C3 C8 C7 108.4(3) . . ?
C3 C9 C10 108.3(3) . . ?
C12 C10 C11 110.2(5) . . ?
C12 C10 C9 111.4(4) . . ?
C11 C10 C9 108.1(4) . . ?
C10 C11 C7 109.0(4) . . ?
C10 C12 C5 109.6(4) . . ?

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
C3 O2 C2 O1 -4.8(5) . . . . ?
C3 O2 C2 C1 174.0(2) . . . . ?
I2 C1 C2 O1 -125.0(3) . . . . ?
I1 C1 C2 O1 109.1(3) . . . . ?
I2 C1 C2 O2 56.1(3) . . . . ?
I1 C1 C2 O2 -69.8(3) . . . . ?
C2 O2 C3 C8 66.6(4) . . . . ?
C2 O2 C3 C4 -176.1(3) . . . . ?
C2 O2 C3 C9 -58.9(4) . . . . ?
O2 C3 C4 C5 179.3(3) . . . . ?
C8 C3 C4 C5 -61.6(4) . . . . ?
C9 C3 C4 C5 60.9(5) . . . . ?
C3 C4 C5 C12 -60.0(5) . . . . ?
C3 C4 C5 C6 60.6(5) . . . . ?
C12 C5 C6 C7 60.0(5) . . . . ?
C4 C5 C6 C7 -60.1(5) . . . . ?
C5 C6 C7 C8 60.9(6) . . . . ?
C5 C6 C7 C11 -58.3(5) . . . . ?
O2 C3 C8 C7 175.8(4) . . . . ?
C4 C3 C8 C7 61.8(5) . . . . ?
C9 C3 C8 C7 -59.3(5) . . . . ?
C6 C7 C8 C3 -61.4(6) . . . . ?
C11 C7 C8 C3 58.1(5) . . . . ?
O2 C3 C9 C10 -173.3(4) . . . . ?
C8 C3 C9 C10 61.3(5) . . . . ?
C4 C3 C9 C10 -59.6(5) . . . . ?
C3 C9 C10 C12 59.4(6) . . . . ?
C3 C9 C10 C11 -61.9(5) . . . . ?
C12 C10 C11 C7 -59.1(5) . . . . ?
C9 C10 C11 C7 62.9(5) . . . . ?
C6 C7 C11 C10 57.6(5) . . . . ?
C8 C7 C11 C10 -61.3(6) . . . . ?
C11 C10 C12 C5 60.9(5) . . . . ?
C9 C10 C12 C5 -59.2(6) . . . . ?
C6 C5 C12 C10 -61.3(5) . . . . ?
C4 C5 C12 C10 58.4(6) . . . . ?

_refine_diff_density_max         1.441
_refine_diff_density_min         -2.211
_refine_diff_density_rms         0.173

